CAS No.1310726-60-3,Upadacitinib Suppliers

Zibo Hangyu Biotechnology Development Co., Ltd

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Chinese Name: Upadacitinib Chinese synonym: ABT-494; upatinib English Name: Upadacitinib English synonyms: Upadacitinib; ABT-494; ABT-494 (Upadacitinib) free base CAS: 1310726-60-3 Molecular formula: C17H19F3N6O Molecular weight:

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Taizhou Crene Biotechnology co.ltd

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TaiChem Taizhou Limited

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Siwei Development Group Ltd.

Product name: Upadacitinib CAS No.：1310726-60-3 Molecule Formula：C17H19F3N6O Molecule Weight：380.37 Purity: 99.0% Package: 25kg/drum Description：White powder Manufacture Standards：Enterprise Standard TESTING ITEMS

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Zibo Dorne chemical technology co. LTD

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Shanghai Minstar Chemical Co., Ltd

Product Name: Upadacitinib Synonyms: Upadacitinib;ABT-494;ABT-494(Upadacitinib) free base;Upadacitinib (ABT-494);ABT-494 (Upadacitinib);Upadacitinib (Rinvoq);ABT-494; ABT494; ABT 494;CS-2730 CAS: 1310726-60-3 MF: C17H19F3N6O MW: 380.37

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Synthetic route

: C22H27F3N6O3

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
With butan-1-ol at 85 - 90℃;	95%

: 753-90-2
trifluoroethylamine

: (3S,4R)-benzyl-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)pyrrolidine-1-carboxylate

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Stage #1: (3S,4R)-benzyl-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)pyrrolidine-1-carboxylate With 2,6-dichloropyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0 - 20℃; Inert atmosphere; Stage #2: trifluoroethylamine In dichloromethane at 20℃; Inert atmosphere;	88%

: 753-90-2
trifluoroethylamine

: 8-((3R,4S)-4-ethylpyrrolidin-3-yl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine bishydrochloride

: 530-62-1
1,1'-carbonyldiimidazole

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Stage #1: trifluoroethylamine; 1,1'-carbonyldiimidazole In tetrahydrofuran at 30℃; for 1.33333h; Stage #2: 8-((3R,4S)-4-ethylpyrrolidin-3-yl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine bishydrochloride With dipotassium hydrogenphosphate; potassium hydroxide In tetrahydrofuran; water at 25℃; for 1h; pH=9; Concentration;	87%

...Expand

: 4556-25-6
trifluoromethylethylamine

: 8-((3R,4S)-4-ethylpyrrolidin-3-yl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Stage #1: trifluoromethylethylamine With triethylamine; 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: 8-((3R,4S)-4-ethylpyrrolidin-3-yl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine In dichloromethane for 6h;	71%

: ethyl N-[5-(4-methylbenzenesulfonyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]carbamate

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: lithium tert-butoxide / N,N-dimethyl acetamide / 0.5 h / -10 - 5 °C 1.2: 1 h / -10 °C 2.1: pyridine; trifluoroacetic anhydride / acetonitrile / 2 h / 75 °C 3.1: 10% palladium hydroxide on charcoal; hydrogen / ethanol / 16 h / 50 °C / 1794.37 Torr 3.2: 1 h 4.1: tetrahydrofuran / 1.33 h / 30 °C 4.2: 1 h / 25 °C / pH 9 View Scheme
Multi-step reaction with 5 steps 1: lithium tert-butoxide / N,N-dimethyl acetamide 2: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 3: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 4: hydrogen; 10 wt% Pd(OH)2 on carbon 5: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme

: dimethylsulfoxonium 2-((3R,4S)-1-benzyloxycarbonyl-4-ethylpyrrolidin-3-yl)-2-oxo-ethylide

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: hydrogen bromide; acetic acid / tetrahydrofuran / 5 h / 40 °C 2.1: lithium tert-butoxide / N,N-dimethyl acetamide / 0.5 h / -10 - 5 °C 2.2: 1 h / -10 °C 3.1: pyridine; trifluoroacetic anhydride / acetonitrile / 2 h / 75 °C 4.1: 10% palladium hydroxide on charcoal; hydrogen / ethanol / 16 h / 50 °C / 1794.37 Torr 4.2: 1 h 5.1: tetrahydrofuran / 1.33 h / 30 °C 5.2: 1 h / 25 °C / pH 9 View Scheme
Multi-step reaction with 6 steps 1: lithium bromide; toluene-4-sulfonic acid 2: lithium tert-butoxide / N,N-dimethyl acetamide 3: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 4: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 5: hydrogen; 10 wt% Pd(OH)2 on carbon 6: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 7 steps 1: lithium bromide; toluene-4-sulfonic acid 2: sodium hydride / N,N-dimethyl-formamide 3: trifluoroacetic acid / dichloromethane 4: Lawessons reagent / 1,4-dioxane / 50 °C 5: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 6: hydrogen; 10 wt% Pd(OH)2 on carbon 7: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme

: 1428243-26-8
(3R,4S)-benzyl 3-(2-bromoacetyl)-4-ethylpyrrolidine-1-carboxylate

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: lithium tert-butoxide / N,N-dimethyl acetamide / 0.5 h / -10 - 5 °C 1.2: 1 h / -10 °C 2.1: pyridine; trifluoroacetic anhydride / acetonitrile / 2 h / 75 °C 3.1: 10% palladium hydroxide on charcoal; hydrogen / ethanol / 16 h / 50 °C / 1794.37 Torr 3.2: 1 h 4.1: tetrahydrofuran / 1.33 h / 30 °C 4.2: 1 h / 25 °C / pH 9 View Scheme
Multi-step reaction with 5 steps 1: lithium tert-butoxide / N,N-dimethyl acetamide 2: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 3: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 4: hydrogen; 10 wt% Pd(OH)2 on carbon 5: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 6 steps 1: sodium hydride / N,N-dimethyl-formamide 2: trifluoroacetic acid / dichloromethane 3: Lawessons reagent / 1,4-dioxane / 50 °C 4: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 5: hydrogen; 10 wt% Pd(OH)2 on carbon 6: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme

: (35,4R)-benzyl 3-ethyl-4-(2-((ethoxycarbonyl)(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)pyrrolidine-1-carboxylate

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: pyridine; trifluoroacetic anhydride / acetonitrile / 2 h / 75 °C 2.1: 10% palladium hydroxide on charcoal; hydrogen / ethanol / 16 h / 50 °C / 1794.37 Torr 2.2: 1 h 3.1: tetrahydrofuran / 1.33 h / 30 °C 3.2: 1 h / 25 °C / pH 9 View Scheme

: 1201186-54-0
2-bromo-5-(p-toluenesulfonyl)-5H-pyrrolo[2,3-b]pyrazine

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium carbonate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / toluene / 95 °C 1.2: 2 h 2.1: lithium tert-butoxide / N,N-dimethyl acetamide / 0.5 h / -10 - 5 °C 2.2: 1 h / -10 °C 3.1: pyridine; trifluoroacetic anhydride / acetonitrile / 2 h / 75 °C 4.1: 10% palladium hydroxide on charcoal; hydrogen / ethanol / 16 h / 50 °C / 1794.37 Torr 4.2: 1 h 5.1: tetrahydrofuran / 1.33 h / 30 °C 5.2: 1 h / 25 °C / pH 9 View Scheme
Multi-step reaction with 6 steps 1: potassium carbonate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / toluene / 95 °C 2: lithium tert-butoxide / N,N-dimethyl acetamide 3: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 4: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 5: hydrogen; 10 wt% Pd(OH)2 on carbon 6: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 7 steps 1: tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos; sodium t-butanolate / 1,4-dioxane / 90 °C 2: sodium hydride / N,N-dimethyl-formamide 3: hydrogenchloride / 1,4-dioxane 4: Lawessons reagent / 1,4-dioxane / 50 °C 5: hydrogen bromide; acetic acid 6: triethylamine / N,N-dimethyl-formamide / 55 °C 7: sodium hydroxide / 1,4-dioxane View Scheme

: (3R,4S)-1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylate

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: phosphoric acid / tert-butyl methyl ether / 0.5 h 1.2: 1.5 h / 20 °C 1.3: 2.25 h / -5 - -1 °C / Reflux 2.1: hydrogen bromide; acetic acid / tetrahydrofuran / 5 h / 40 °C 3.1: lithium tert-butoxide / N,N-dimethyl acetamide / 0.5 h / -10 - 5 °C 3.2: 1 h / -10 °C 4.1: pyridine; trifluoroacetic anhydride / acetonitrile / 2 h / 75 °C 5.1: 10% palladium hydroxide on charcoal; hydrogen / ethanol / 16 h / 50 °C / 1794.37 Torr 5.2: 1 h 6.1: tetrahydrofuran / 1.33 h / 30 °C 6.2: 1 h / 25 °C / pH 9 View Scheme
Multi-step reaction with 7 steps 1: 1,1'-carbonyldiimidazole 2: lithium bromide; toluene-4-sulfonic acid 3: lithium tert-butoxide / N,N-dimethyl acetamide 4: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 5: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 6: hydrogen; 10 wt% Pd(OH)2 on carbon 7: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 7 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 2: acetonitrile; tetrahydrofuran / 0 °C 3: lithium tert-butoxide / N,N-dimethyl acetamide 4: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 5: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 6: hydrogen; 10 wt% Pd(OH)2 on carbon 7: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme

: 875781-43-4
2-bromo-5H-pyrrolo[2,3-b]pyrazine

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: sodium hydride / N,N-dimethyl-formamide 2: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 95 °C 3: hydrogenchloride; water / 1,4-dioxane / 50 °C 4: diphenyl phosphoryl azide; triethylamine / 70 °C 5: sodium hydride / N,N-dimethyl-formamide 6: hydrogenchloride / 1,4-dioxane 7: Lawessons reagent / 1,4-dioxane / 50 °C 8: hydrogen bromide; acetic acid 9: triethylamine / N,N-dimethyl-formamide / 55 °C 10: sodium hydroxide / 1,4-dioxane View Scheme
Multi-step reaction with 10 steps 1: sodium hydride / N,N-dimethyl-formamide 2: bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 95 °C 3: hydrogenchloride; water / 1,4-dioxane / 50 °C 4: diphenyl phosphoryl azide; triethylamine / 70 °C 5: sodium hydride / N,N-dimethyl-formamide 6: trifluoroacetic acid / dichloromethane 7: Lawessons reagent / 1,4-dioxane / 50 °C 8: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 9: hydrogen; 10 wt% Pd(OH)2 on carbon 10: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 7 steps 1: sodium hydride / N,N-dimethyl-formamide 2: potassium carbonate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene / toluene / 95 °C 3: lithium tert-butoxide / N,N-dimethyl acetamide 4: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 5: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 6: hydrogen; 10 wt% Pd(OH)2 on carbon 7: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme

: methyl 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carboxylate

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: hydrogenchloride; water / 1,4-dioxane / 50 °C 2: diphenyl phosphoryl azide; triethylamine / 70 °C 3: sodium hydride / N,N-dimethyl-formamide 4: hydrogenchloride / 1,4-dioxane 5: Lawessons reagent / 1,4-dioxane / 50 °C 6: hydrogen bromide; acetic acid 7: triethylamine / N,N-dimethyl-formamide / 55 °C 8: sodium hydroxide / 1,4-dioxane View Scheme
Multi-step reaction with 8 steps 1: hydrogenchloride; water / 1,4-dioxane / 50 °C 2: diphenyl phosphoryl azide; triethylamine / 70 °C 3: sodium hydride / N,N-dimethyl-formamide 4: trifluoroacetic acid / dichloromethane 5: Lawessons reagent / 1,4-dioxane / 50 °C 6: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 7: hydrogen; 10 wt% Pd(OH)2 on carbon 8: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme

Yield

Multi-step reaction with 8 steps
1: hydrogenchloride; water / 1,4-dioxane / 50 °C
2: diphenyl phosphoryl azide; triethylamine / 70 °C
3: sodium hydride / N,N-dimethyl-formamide
4: hydrogenchloride / 1,4-dioxane
5: Lawessons reagent / 1,4-dioxane / 50 °C
6: hydrogen bromide; acetic acid
7: triethylamine / N,N-dimethyl-formamide / 55 °C
8: sodium hydroxide / 1,4-dioxane
View Scheme

Multi-step reaction with 8 steps
1: hydrogenchloride; water / 1,4-dioxane / 50 °C
2: diphenyl phosphoryl azide; triethylamine / 70 °C
3: sodium hydride / N,N-dimethyl-formamide
4: trifluoroacetic acid / dichloromethane
5: Lawessons reagent / 1,4-dioxane / 50 °C
6: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C
7: hydrogen; 10 wt% Pd(OH)2 on carbon
8: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran
View Scheme

: 5-tosylpyrrolo[2,3-b]pyrazine-2-carboxylic acid hydrochloride

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: diphenyl phosphoryl azide; triethylamine / 70 °C 2: sodium hydride / N,N-dimethyl-formamide 3: hydrogenchloride / 1,4-dioxane 4: Lawessons reagent / 1,4-dioxane / 50 °C 5: hydrogen bromide; acetic acid 6: triethylamine / N,N-dimethyl-formamide / 55 °C 7: sodium hydroxide / 1,4-dioxane View Scheme
Multi-step reaction with 7 steps 1: diphenyl phosphoryl azide; triethylamine / 70 °C 2: sodium hydride / N,N-dimethyl-formamide 3: trifluoroacetic acid / dichloromethane 4: Lawessons reagent / 1,4-dioxane / 50 °C 5: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 6: hydrogen; 10 wt% Pd(OH)2 on carbon 7: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme

: 1201187-44-1
N-(5-(p-toluenesulfonyl)pyrrolo[2,3-b]pyrazin-2-yl)carbamic acid tert-butyl ester

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: sodium hydride / N,N-dimethyl-formamide 2: trifluoroacetic acid / dichloromethane 3: Lawessons reagent / 1,4-dioxane / 50 °C 4: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 5: hydrogen; 10 wt% Pd(OH)2 on carbon 6: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 6 steps 1: sodium hydride / N,N-dimethyl-formamide 2: hydrogenchloride / 1,4-dioxane 3: Lawessons reagent / 1,4-dioxane / 50 °C 4: hydrogen bromide; acetic acid 5: triethylamine / N,N-dimethyl-formamide / 55 °C 6: sodium hydroxide / 1,4-dioxane View Scheme
Multi-step reaction with 6 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1.5 h / 0 °C 1.2: 1 h / 0 °C 2.1: trifluoroacetic acid / dichloromethane / 4 h / 5 - 27 °C 3.1: Lawessons reagent / toluene; 1,4-dioxane / 4 h / 27 - 80 °C / Inert atmosphere 4.1: acetic acid; hydrogen bromide / 1,4-dioxane / 3 h / 27 - 60 °C 5.1: N,N-dimethyl-formamide / 16 h / 27 - 65 °C 5.2: 1 h / 27 - 65 °C 6.1: water; sodium hydroxide / 1,4-dioxane / 1 h / 27 - 55 °C View Scheme
Multi-step reaction with 5 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 2.1: trifluoroacetic anhydride / acetonitrile / 4 h / 75 °C 3.1: sodium hydroxide / tetrahydrofuran; water / 2 h / 30 °C 4.1: hydrogen; palladium 10% on activated carbon; 1,4-diaza-bicyclo[2.2.2]octane / ethanol; acetic acid / 15 h / 3800.26 Torr 5.1: triethylamine; 1,1'-carbonyldiimidazole / dichloromethane / 0.5 h / 20 °C 5.2: 6 h View Scheme
Multi-step reaction with 6 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 2 h 3.1: trifluoroacetic anhydride / acetonitrile / 3 h / 75 °C 4.1: sodium hydroxide / tetrahydrofuran; water / 2 h / 30 °C 5.1: hydrogen; palladium 10% on activated carbon; 1,4-diaza-bicyclo[2.2.2]octane / ethanol; acetic acid / 15 h / 3800.26 Torr 6.1: triethylamine; 1,1'-carbonyldiimidazole / dichloromethane / 0.5 h / 20 °C 6.2: 6 h View Scheme

: C16H20BrNO3

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: sodium hydride / N,N-dimethyl-formamide 2: hydrogenchloride / 1,4-dioxane 3: Lawessons reagent / 1,4-dioxane / 50 °C 4: hydrogen bromide; acetic acid 5: triethylamine / N,N-dimethyl-formamide / 55 °C 6: sodium hydroxide / 1,4-dioxane View Scheme

: C34H39N5O7S

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: hydrogenchloride / 1,4-dioxane 2: Lawessons reagent / 1,4-dioxane / 50 °C 3: hydrogen bromide; acetic acid 4: triethylamine / N,N-dimethyl-formamide / 55 °C 5: sodium hydroxide / 1,4-dioxane View Scheme

: benzyl 3-ethyl-4-(2-((5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)amino)acetyl)pyrrolidine-1-carboxylate

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Lawessons reagent / 1,4-dioxane / 50 °C 2: hydrogen bromide; acetic acid 3: triethylamine / N,N-dimethyl-formamide / 55 °C 4: sodium hydroxide / 1,4-dioxane View Scheme

: C29H29N5O4S

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen bromide; acetic acid 2: triethylamine / N,N-dimethyl-formamide / 55 °C 3: sodium hydroxide / 1,4-dioxane View Scheme

: C21H23N5O2S

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 55 °C 2: sodium hydroxide / 1,4-dioxane View Scheme

: 1046861-47-5
N-(2,2,2-trifluoroethyl)-1H-imidazole-1-carboxamide

: 8-((3R,4S)-4-ethylpyrrolidin-3-yl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine bishydrochloride

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
With dipotassium hydrogenphosphate; potassium hydroxide In tetrahydrofuran

: C24H25F3N6O3S

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane

: 55314-57-3
ethyl pent-2-ynoate

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1: hydrogen; pyridine / tetrahydrofuran 2: trifluoroacetic acid / dichloromethane 3: hydrogen; 10 wt% Pd(OH)2 on carbon / ethanol 4: hydrogenchloride; water / 80 °C 5: sodium carbonate / 1,4-dioxane; water 6: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 7: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 8: acetonitrile; tetrahydrofuran / 0 °C 9: lithium tert-butoxide / N,N-dimethyl acetamide 10: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 11: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 12: hydrogen; 10 wt% Pd(OH)2 on carbon 13: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 13 steps 1: hydrogen; pyridine / tetrahydrofuran 2: trifluoroacetic acid / dichloromethane 3: hydrogen; 10 wt% Pd(OH)2 on carbon / ethanol 4: hydrogenchloride; water / 80 °C 5: sodium carbonate / 1,4-dioxane; water 6: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 7: acetonitrile; tetrahydrofuran / 0 °C 8: sodium hydride / N,N-dimethyl-formamide 9: hydrogenchloride / 1,4-dioxane 10: Lawessons reagent / 1,4-dioxane / 50 °C 11: hydrogen bromide; acetic acid 12: triethylamine / N,N-dimethyl-formamide / 55 °C 13: sodium hydroxide / 1,4-dioxane View Scheme
Multi-step reaction with 13 steps 1: hydrogen; pyridine / tetrahydrofuran 2: trifluoroacetic acid / dichloromethane 3: hydrogen; 10 wt% Pd(OH)2 on carbon / ethanol 4: hydrogenchloride; water / 80 °C 5: sodium carbonate / 1,4-dioxane; water 6: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 7: 1,1'-carbonyldiimidazole 8: lithium bromide; toluene-4-sulfonic acid 9: lithium tert-butoxide / N,N-dimethyl acetamide 10: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 11: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 12: hydrogen; 10 wt% Pd(OH)2 on carbon 13: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme

: 24410-84-2
ethyl (2E)-pentenoate

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: trifluoroacetic acid / dichloromethane 2: hydrogen; 10 wt% Pd(OH)2 on carbon / ethanol 3: hydrogenchloride; water / 80 °C 4: sodium carbonate / 1,4-dioxane; water 5: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 6: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 7: acetonitrile; tetrahydrofuran / 0 °C 8: lithium tert-butoxide / N,N-dimethyl acetamide 9: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 10: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 11: hydrogen; 10 wt% Pd(OH)2 on carbon 12: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 12 steps 1: trifluoroacetic acid / dichloromethane 2: hydrogen; 10 wt% Pd(OH)2 on carbon / ethanol 3: hydrogenchloride; water / 80 °C 4: sodium carbonate / 1,4-dioxane; water 5: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 6: acetonitrile; tetrahydrofuran / 0 °C 7: sodium hydride / N,N-dimethyl-formamide 8: hydrogenchloride / 1,4-dioxane 9: Lawessons reagent / 1,4-dioxane / 50 °C 10: hydrogen bromide; acetic acid 11: triethylamine / N,N-dimethyl-formamide / 55 °C 12: sodium hydroxide / 1,4-dioxane View Scheme
Multi-step reaction with 12 steps 1: trifluoroacetic acid / dichloromethane 2: hydrogen; 10 wt% Pd(OH)2 on carbon / ethanol 3: hydrogenchloride; water / 80 °C 4: sodium carbonate / 1,4-dioxane; water 5: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 6: 1,1'-carbonyldiimidazole 7: lithium bromide; toluene-4-sulfonic acid 8: lithium tert-butoxide / N,N-dimethyl acetamide 9: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 10: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 11: hydrogen; 10 wt% Pd(OH)2 on carbon 12: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 13 steps 1: trifluoroacetic acid / dichloromethane 2: hydrogen; 10 wt% Pd(OH)2 on carbon / ethanol 3: hydrogenchloride; water / 80 °C 4: sodium carbonate / 1,4-dioxane; water 5: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 6: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 7: acetonitrile; tetrahydrofuran / 0 °C 8: sodium hydride / N,N-dimethyl-formamide 9: trifluoroacetic acid / dichloromethane 10: Lawessons reagent / 1,4-dioxane / 50 °C 11: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 12: hydrogen; 10 wt% Pd(OH)2 on carbon 13: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 13 steps 1: trifluoroacetic acid / dichloromethane 2: hydrogen; 10 wt% Pd(OH)2 on carbon / ethanol 3: hydrogenchloride; water / 80 °C 4: sodium carbonate / 1,4-dioxane; water 5: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 6: 1,1'-carbonyldiimidazole 7: lithium bromide; toluene-4-sulfonic acid 8: sodium hydride / N,N-dimethyl-formamide 9: trifluoroacetic acid / dichloromethane 10: Lawessons reagent / 1,4-dioxane / 50 °C 11: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 12: hydrogen; 10 wt% Pd(OH)2 on carbon 13: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme

: ethyl 1-benzyl-4-ethylpyrrolidine-3-carboxylate

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: hydrogen; 10 wt% Pd(OH)2 on carbon / ethanol 2: hydrogenchloride; water / 80 °C 3: sodium carbonate / 1,4-dioxane; water 4: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 5: 1,1'-carbonyldiimidazole 6: lithium bromide; toluene-4-sulfonic acid 7: lithium tert-butoxide / N,N-dimethyl acetamide 8: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 9: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 10: hydrogen; 10 wt% Pd(OH)2 on carbon 11: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 11 steps 1: hydrogen; 10 wt% Pd(OH)2 on carbon / ethanol 2: hydrogenchloride; water / 80 °C 3: sodium carbonate / 1,4-dioxane; water 4: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 5: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 6: acetonitrile; tetrahydrofuran / 0 °C 7: lithium tert-butoxide / N,N-dimethyl acetamide 8: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 9: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 10: hydrogen; 10 wt% Pd(OH)2 on carbon 11: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 11 steps 1: hydrogen; 10 wt% Pd(OH)2 on carbon / ethanol 2: hydrogenchloride; water / 80 °C 3: sodium carbonate / 1,4-dioxane; water 4: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 5: acetonitrile; tetrahydrofuran / 0 °C 6: sodium hydride / N,N-dimethyl-formamide 7: hydrogenchloride / 1,4-dioxane 8: Lawessons reagent / 1,4-dioxane / 50 °C 9: hydrogen bromide; acetic acid 10: triethylamine / N,N-dimethyl-formamide / 55 °C 11: sodium hydroxide / 1,4-dioxane View Scheme

: ethyl 4-ethylpyrrolidine-3-carboxylate

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: hydrogenchloride; water / 80 °C 2: sodium carbonate / 1,4-dioxane; water 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 4: acetonitrile; tetrahydrofuran / 0 °C 5: sodium hydride / N,N-dimethyl-formamide 6: hydrogenchloride / 1,4-dioxane 7: Lawessons reagent / 1,4-dioxane / 50 °C 8: hydrogen bromide; acetic acid 9: triethylamine / N,N-dimethyl-formamide / 55 °C 10: sodium hydroxide / 1,4-dioxane View Scheme
Multi-step reaction with 10 steps 1: hydrogenchloride; water / 80 °C 2: sodium carbonate / 1,4-dioxane; water 3: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 4: 1,1'-carbonyldiimidazole 5: lithium bromide; toluene-4-sulfonic acid 6: lithium tert-butoxide / N,N-dimethyl acetamide 7: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 8: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 9: hydrogen; 10 wt% Pd(OH)2 on carbon 10: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 10 steps 1: hydrogenchloride; water / 80 °C 2: sodium carbonate / 1,4-dioxane; water 3: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 4: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 5: acetonitrile; tetrahydrofuran / 0 °C 6: lithium tert-butoxide / N,N-dimethyl acetamide 7: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 8: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 9: hydrogen; 10 wt% Pd(OH)2 on carbon 10: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 11 steps 1: hydrogenchloride; water / 80 °C 2: sodium carbonate / 1,4-dioxane; water 3: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 4: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 5: acetonitrile; tetrahydrofuran / 0 °C 6: sodium hydride / N,N-dimethyl-formamide 7: trifluoroacetic acid / dichloromethane 8: Lawessons reagent / 1,4-dioxane / 50 °C 9: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 10: hydrogen; 10 wt% Pd(OH)2 on carbon 11: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 11 steps 1: hydrogenchloride; water / 80 °C 2: sodium carbonate / 1,4-dioxane; water 3: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 4: 1,1'-carbonyldiimidazole 5: lithium bromide; toluene-4-sulfonic acid 6: sodium hydride / N,N-dimethyl-formamide 7: trifluoroacetic acid / dichloromethane 8: Lawessons reagent / 1,4-dioxane / 50 °C 9: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 10: hydrogen; 10 wt% Pd(OH)2 on carbon 11: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme

: 4-ethylpyrrolidine-3-carboxylic acid

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: sodium carbonate / 1,4-dioxane; water 2: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 4: acetonitrile; tetrahydrofuran / 0 °C 5: sodium hydride / N,N-dimethyl-formamide 6: trifluoroacetic acid / dichloromethane 7: Lawessons reagent / 1,4-dioxane / 50 °C 8: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 9: hydrogen; 10 wt% Pd(OH)2 on carbon 10: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 10 steps 1: sodium carbonate / 1,4-dioxane; water 2: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 3: 1,1'-carbonyldiimidazole 4: lithium bromide; toluene-4-sulfonic acid 5: sodium hydride / N,N-dimethyl-formamide 6: trifluoroacetic acid / dichloromethane 7: Lawessons reagent / 1,4-dioxane / 50 °C 8: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 9: hydrogen; 10 wt% Pd(OH)2 on carbon 10: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 9 steps 1: sodium carbonate / 1,4-dioxane; water 2: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 3: 1,1'-carbonyldiimidazole 4: lithium bromide; toluene-4-sulfonic acid 5: lithium tert-butoxide / N,N-dimethyl acetamide 6: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 7: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 8: hydrogen; 10 wt% Pd(OH)2 on carbon 9: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme

: C12H21NO4

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: trifluoroacetic acid 2: sodium carbonate / 1,4-dioxane; water 3: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 4: 1,1'-carbonyldiimidazole 5: lithium bromide; toluene-4-sulfonic acid 6: lithium tert-butoxide / N,N-dimethyl acetamide 7: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 8: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 9: hydrogen; 10 wt% Pd(OH)2 on carbon 10: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 10 steps 1: trifluoroacetic acid 2: sodium carbonate / 1,4-dioxane; water 3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 4: acetonitrile; tetrahydrofuran / 0 °C 5: sodium hydride / N,N-dimethyl-formamide 6: hydrogenchloride / 1,4-dioxane 7: Lawessons reagent / 1,4-dioxane / 50 °C 8: hydrogen bromide; acetic acid 9: triethylamine / N,N-dimethyl-formamide / 55 °C 10: sodium hydroxide / 1,4-dioxane View Scheme
Multi-step reaction with 10 steps 1: trifluoroacetic acid 2: sodium carbonate / 1,4-dioxane; water 3: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 4: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 5: acetonitrile; tetrahydrofuran / 0 °C 6: lithium tert-butoxide / N,N-dimethyl acetamide 7: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 8: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 9: hydrogen; 10 wt% Pd(OH)2 on carbon 10: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 11 steps 1: trifluoroacetic acid 2: sodium carbonate / 1,4-dioxane; water 3: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 4: 1,1'-carbonyldiimidazole 5: lithium bromide; toluene-4-sulfonic acid 6: sodium hydride / N,N-dimethyl-formamide 7: trifluoroacetic acid / dichloromethane 8: Lawessons reagent / 1,4-dioxane / 50 °C 9: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 10: hydrogen; 10 wt% Pd(OH)2 on carbon 11: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 11 steps 1: trifluoroacetic acid 2: sodium carbonate / 1,4-dioxane; water 3: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 4: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 5: acetonitrile; tetrahydrofuran / 0 °C 6: sodium hydride / N,N-dimethyl-formamide 7: trifluoroacetic acid / dichloromethane 8: Lawessons reagent / 1,4-dioxane / 50 °C 9: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 10: hydrogen; 10 wt% Pd(OH)2 on carbon 11: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme

: 1-((benzyloxy)carbonyl)-4-ethylpyrrolidine-3-carboxylic acid

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 2: acetonitrile; tetrahydrofuran / 0 °C 3: sodium hydride / N,N-dimethyl-formamide 4: hydrogenchloride / 1,4-dioxane 5: Lawessons reagent / 1,4-dioxane / 50 °C 6: hydrogen bromide; acetic acid 7: triethylamine / N,N-dimethyl-formamide / 55 °C 8: sodium hydroxide / 1,4-dioxane View Scheme
Multi-step reaction with 8 steps 1: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 3: acetonitrile; tetrahydrofuran / 0 °C 4: lithium tert-butoxide / N,N-dimethyl acetamide 5: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 6: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 7: hydrogen; 10 wt% Pd(OH)2 on carbon 8: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme
Multi-step reaction with 8 steps 1: (R)-1-(1-Naphthyl)ethylamine / acetonitrile 2: 1,1'-carbonyldiimidazole 3: lithium bromide; toluene-4-sulfonic acid 4: lithium tert-butoxide / N,N-dimethyl acetamide 5: pyridine; trifluoroacetic anhydride / acetonitrile / 75 °C 6: sodium hydroxide / 2-methyltetrahydrofuran / 55 °C 7: hydrogen; 10 wt% Pd(OH)2 on carbon 8: dipotassium hydrogenphosphate; potassium hydroxide / tetrahydrofuran View Scheme

: C15H18ClNO3

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: acetonitrile; tetrahydrofuran / 0 °C 2: sodium hydride / N,N-dimethyl-formamide 3: hydrogenchloride / 1,4-dioxane 4: Lawessons reagent / 1,4-dioxane / 50 °C 5: hydrogen bromide; acetic acid 6: triethylamine / N,N-dimethyl-formamide / 55 °C 7: sodium hydroxide / 1,4-dioxane View Scheme

: 87-69-4
L-Tartaric acid

: 1310726-60-3
(3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

: (2R,3R)-2,3-dihydroxybutanedioic acid (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide

Conditions

Conditions	Yield
In water at 20℃; Solvent;
In water at 0℃;

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