N-(6-acetyl-2-methyl-3-methoxyphenyl)-4-isopropylthiazole-2-carboxamide
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Stage #1: N-(6-acetyl-2-methyl-3-methoxyphenyl)-4-isopropylthiazole-2-carboxamide With potassium tert-butylate In tert-butyl alcohol for 18h; Reflux; Inert atmosphere; Stage #2: With hydrogenchloride In water; ethyl acetate at 20℃; | 99% |
With potassium tert-butylate In tert-butyl alcohol for 18h; Inert atmosphere; Reflux; | 99% |
With potassium tert-butylate In tert-butyl alcohol at 100℃; for 8h; | 90% |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
With hydrogenchloride In water for 14h; Inert atmosphere; Reflux; | 80% |
3-methyl-butan-2-one
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: bromine / methanol / 3 h / -30 - 20 °C / Inert atmosphere 2.1: ethanol / 1.5 h / Inert atmosphere; Reflux 3.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere 4.1: HATU / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere 4.2: Inert atmosphere 5.1: potassium tert-butylate / tert-butyl alcohol / 18 h / Inert atmosphere; Reflux View Scheme |
1-(2-amino-4-methoxy-3-methyl-phenyl)ethanone
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: HATU / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: potassium tert-butylate / tert-butyl alcohol / 18 h / Inert atmosphere; Reflux View Scheme |
4-isopropylthiazole-2-carboxylic acid
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: HATU / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: potassium tert-butylate / tert-butyl alcohol / 18 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 3 steps 1: oxalyl dichloride / dichloromethane / 4.5 h / 0 - 20 °C 2: acetone / 4.5 h / 0 - 20 °C 3: potassium tert-butylate / tert-butyl alcohol / 8 h / 100 °C View Scheme |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere 2.1: HATU / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: potassium tert-butylate / tert-butyl alcohol / 18 h / Inert atmosphere; Reflux View Scheme |
1-bromo-3-methyl-2-butanone
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: ethanol / 1.5 h / Inert atmosphere; Reflux 2.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere 3.1: HATU / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere 3.2: Inert atmosphere 4.1: potassium tert-butylate / tert-butyl alcohol / 18 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 5 steps 1: ethanol / 2 h / 75 °C 2: lithium hydroxide monohydrate / methanol / 3.5 h / 0 - 20 °C 3: oxalyl dichloride / dichloromethane / 4.5 h / 0 - 20 °C 4: acetone / 4.5 h / 0 - 20 °C 5: potassium tert-butylate / tert-butyl alcohol / 8 h / 100 °C View Scheme |
2-methyl-3-methoxyaniline
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: boron trichloride / dichloromethane; para-xylene / 0.5 h / 0 °C / Inert atmosphere 1.2: 0.5 h / 0 °C / Inert atmosphere 1.3: 19.75 h / 0 - 70 °C / Inert atmosphere 2.1: HATU / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: potassium tert-butylate / tert-butyl alcohol / 18 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 7 steps 1: methanol / 4 h / 20 °C 2: Eaton′s Reagent / 1 h / 50 °C 3: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C 4: ammonia / methanol / 20 °C 5: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere 6: methanol / 48 h / 20 °C 7: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 7 steps 1: methanol / 4 h / 20 °C 2: Eaton′s Reagent / 1 h / 50 °C 3: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C 4: magnesium chloride / acetonitrile / 20 h / 80 °C 5: tetraphosphorus decasulfide; pyridine / 10 h / 110 °C / Inert atmosphere 6: manganese(IV) oxide / 24 h / Reflux 7: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 8 steps 1: methanol / 4 h / 20 °C 2: Eaton′s Reagent / 1 h / 50 °C 3: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C 4: ammonia / methanol / 20 °C 5: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere 6: potassium carbonate / methanol / 24 h / 50 °C 7: isopropyl alcohol / 24 h / 100 °C 8: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tetraphosphorus decasulfide; pyridine / 10 h / 110 °C / Inert atmosphere 2: manganese(IV) oxide / 24 h / Reflux 3: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: manganese(IV) oxide / 24 h / Reflux 2: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere 2: methanol / 48 h / 20 °C 3: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 4 steps 1: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere 2: potassium carbonate / methanol / 24 h / 50 °C 3: isopropyl alcohol / 24 h / 100 °C 4: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: methanol / 48 h / 20 °C 2: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate / methanol / 24 h / 50 °C 2: isopropyl alcohol / 24 h / 100 °C 3: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme |
dimethyl 2-(3-methoxy-2-methylphenylamino)-2-butenedioate
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: Eaton′s Reagent / 1 h / 50 °C 2: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C 3: ammonia / methanol / 20 °C 4: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere 5: methanol / 48 h / 20 °C 6: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 6 steps 1: Eaton′s Reagent / 1 h / 50 °C 2: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C 3: magnesium chloride / acetonitrile / 20 h / 80 °C 4: tetraphosphorus decasulfide; pyridine / 10 h / 110 °C / Inert atmosphere 5: manganese(IV) oxide / 24 h / Reflux 6: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 7 steps 1: Eaton′s Reagent / 1 h / 50 °C 2: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C 3: ammonia / methanol / 20 °C 4: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere 5: potassium carbonate / methanol / 24 h / 50 °C 6: isopropyl alcohol / 24 h / 100 °C 7: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: isopropyl alcohol / 24 h / 100 °C 2: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme |
methyl 4-hydroxy-7-methoxy-8-methylquinoline-2-carboxylate
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C 2: ammonia / methanol / 20 °C 3: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere 4: methanol / 48 h / 20 °C 5: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C 2: magnesium chloride / acetonitrile / 20 h / 80 °C 3: tetraphosphorus decasulfide; pyridine / 10 h / 110 °C / Inert atmosphere 4: manganese(IV) oxide / 24 h / Reflux 5: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 6 steps 1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C 2: ammonia / methanol / 20 °C 3: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere 4: potassium carbonate / methanol / 24 h / 50 °C 5: isopropyl alcohol / 24 h / 100 °C 6: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: ammonia / methanol / 20 °C 2: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere 3: methanol / 48 h / 20 °C 4: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 4 steps 1: magnesium chloride / acetonitrile / 20 h / 80 °C 2: tetraphosphorus decasulfide; pyridine / 10 h / 110 °C / Inert atmosphere 3: manganese(IV) oxide / 24 h / Reflux 4: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 5 steps 1: ammonia / methanol / 20 °C 2: Lawessons reagent / tetrahydrofuran / 5 h / Inert atmosphere 3: potassium carbonate / methanol / 24 h / 50 °C 4: isopropyl alcohol / 24 h / 100 °C 5: hydrogenchloride / water / 14 h / Inert atmosphere; Reflux View Scheme |
4-(1-methylethyl)thiazole-2-carboxylic acid ethyl ester
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: lithium hydroxide monohydrate / methanol / 3.5 h / 0 - 20 °C 2: oxalyl dichloride / dichloromethane / 4.5 h / 0 - 20 °C 3: acetone / 4.5 h / 0 - 20 °C 4: potassium tert-butylate / tert-butyl alcohol / 8 h / 100 °C View Scheme |
4-isopropylthiazole-2-carbonyl chloride
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: acetone / 4.5 h / 0 - 20 °C 2: potassium tert-butylate / tert-butyl alcohol / 8 h / 100 °C View Scheme |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
With NaOH In trichlorophosphate | 96% |
With sodium hydroxide; trichlorophosphate | 4.11 g (91%) |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester
C28H35N3O6S
Conditions | Yield |
---|---|
With 2-(diphenylphosphino)pyridine; di-isopropyl azodicarboxylate In tetrahydrofuran at -15 - 20℃; for 17h; | 85% |
With 2-(diphenylphosphino)pyridine; di-tert-butyl-diazodicarboxylate In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; | 80% |
With di-isopropyl azodicarboxylate In tetrahydrofuran at -15 - 20℃; Mitsunobu reaction; |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 50℃; | 80% |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 50℃; | 80% |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
(1R,2R,4S)-1-benzyl 2-methyl 4-hydroxycyclopentane-1,2-dicarboxylate
C32H34N2O6S
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 0 - 20℃; for 2h; Product distribution / selectivity; Mitsunobu reaction; | 75% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Product distribution / selectivity; Mitsunobu reaction; | 71% |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
C26H35BrN2O8S2
C37H48N4O7S2
Conditions | Yield |
---|---|
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 75℃; | 74% |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -15℃; for 4h; Mitsunobu Displacement; Inert atmosphere; | 72% |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
methyl (1R,2R,4R)-2-[5-hexen-1-yl-(methyl)carbamoyl]-4-hydroxycyclopentanecarboxylate
methyl (1R,2R,4S)-2-[5-hexen-1-yl(methyl)carbamoyl]-4-[[2-(4-isopropyl-1,3-thiazol-2-yl)-7-methoxy-8-methyl-4-quinolinyl]oxy]cyclopentanecarboxylate
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 0 - 20℃; for 19 - 20h; Product distribution / selectivity; | 71% |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
ethyl(2S,6S,13aS,14aR,16aS)-6-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate
Conditions | Yield |
---|---|
Stage #1: 8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol; ethyl(2S,6S,13aS,14aR,16aS)-6-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-hydroxy-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxylate With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 18h; Stage #3: With hydrogenchloride In tetrahydrofuran; methanol | 61% |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
C21H32N2O8S
C37H46N4O7S
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 70℃; | 58% |
(1R,2S)-1-{[(1R,2R,4S)-2-(hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
ethyl (1R,2S)-2-ethenyl-1-({[(1R,2R,4R)-2-[hex-5-en-1-yl-(methyl)carbamoyl]-4-({7-methoxy-8-methyl-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinolin-4-yl}oxy)cyclopentyl]carbonyl}-amino)cyclopropanecarboxylate
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -15℃; for 4.5h; | 56% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -15℃; for 4.5h; | 56% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -15 - 20℃; Mitsunobu reaction; |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -15℃; for 4.5h; | 56% |
C25H32BrN3O9S2
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
C36H45N5O8S2
Conditions | Yield |
---|---|
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 75℃; | 45% |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
C19H28N2O8S
C35H42N4O7S
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 12h; | 30% |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Stage #1: 8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol; (1R,4R,6S,15R,18R)-18-(4-bromobenzenesulfonyloxy)-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.4.0.0]nonadec-7-ene-4-carboxylic acid methyl ester at 70℃; for 40h; Stage #2: With potassium carbonate In 1-methyl-pyrrolidin-2-one at 85℃; for 4h; | 27% |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
(1R,4S,14S,Z)-ethyl 4-(2-(2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yloxy)ethyl)-7-methyl-3,6-dioxo-2,5,7-triazabicyclo[12.1.0]pentadec-12-ene-1-carboxylate
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction; | 26% |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
18-hydroxy-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo-[14.3.0.0*4,6*]nonadec-7-ene-4-carboxyric acid ethyl ester
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Product distribution / selectivity; |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
C21H32N2O5
C38H48N4O6S
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine at -20 - 20℃; Mitsunobu reaction; |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
C22H34N2O5
C39H50N4O6S
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine at -20 - 20℃; Mitsunobu reaction; |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
C37H46N4O7S
Conditions | Yield |
---|---|
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 50℃; for 15h; Sealed tube; |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
(2R,6S,13aS,14aR,16aS)-N-(cyclopropylsulfonyl)-2-{[8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinyl]oxy}-5,16-dioxo-6-[(1-pyrrolidinylcarbonyl)amino]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxamide
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 18 h / 0 - 20 °C / Inert atmosphere 2.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere 3.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 40 °C / Inert atmosphere 3.2: 18 h / 40 °C / Inert atmosphere 4.1: hydrogenchloride / 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide / 3 h / Inert atmosphere 5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 5.2: Inert atmosphere View Scheme |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 18 h / 0 - 20 °C / Inert atmosphere 2.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere 3.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 40 °C / Inert atmosphere 3.2: 18 h / 40 °C / Inert atmosphere 4.1: hydrogenchloride / 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide / 3 h / Inert atmosphere 5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 5.2: Inert atmosphere View Scheme |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 18 h / 0 - 20 °C / Inert atmosphere 2.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere 3.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 40 °C / Inert atmosphere 3.2: 18 h / 40 °C / Inert atmosphere 4.1: hydrogenchloride / 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide / 3 h / Inert atmosphere 5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 5.2: Inert atmosphere View Scheme |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
(2R,6S,13aS,14aR,16aS)-N-(cyclopropylsulfonyl)-6-{[(4-hydroxy-1-piperidinyl)carbonyl]amino}-2-{[8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinyl]oxy}-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16 ,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxamide
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 18 h / 0 - 20 °C / Inert atmosphere 2.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere 3.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 40 °C / Inert atmosphere 3.2: 18 h / 40 °C / Inert atmosphere 4.1: hydrogenchloride / 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide / 3 h / Inert atmosphere 5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 5.2: Inert atmosphere View Scheme |
8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinol
(2R,6S,13aS,14aR,16aS)-N-(cyclopropylsulfonyl)-6-({[4-(hydroxymethyl)-1-piperidinyl]carbonyl}amino)-2-{[8-methyl-2-[4-(1-methylethyl)-1,3-thiazol-2-yl]-7-(methyloxy)-4-quinolinyl]oxy}-5,16-dioxo-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5H)-carboxamide
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 18 h / 0 - 20 °C / Inert atmosphere 2.1: lithium hydroxide / tetrahydrofuran; methanol; water / 18 h / 20 °C / Inert atmosphere 3.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 40 °C / Inert atmosphere 3.2: 18 h / 40 °C / Inert atmosphere 4.1: hydrogenchloride / 1,4-dioxane; water; ethyl acetate; N,N-dimethyl-formamide / 3 h / Inert atmosphere 5.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 5.2: Inert atmosphere View Scheme |
The 2-(4-Isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol, with the cas registry number 923289-21-8, has other names as 4-quinolinol, 7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]-.
The physical properties of this chemical are as follows: (1)ACD/LogP: 5.71; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.03; (4)ACD/LogD (pH 7.4): 4.88; (5)#H bond acceptors: 4; (6)#H bond donors: 1; (7)#Freely Rotating Bonds: 4; (8)Polar Surface Area: 83.48 ; (9)Index of Refraction: 1.635; (10)Molar Refractivity: 90.82 cm3; (11)Molar Volume: 253.5 cm3; (12)Polarizability: 36×10-24 cm3; (13)Surface Tension: 51.8 dyne/cm; (14)Density: 1.24 g/cm3; (15)Flash Point: 267.1 °C; (16)Enthalpy of Vaporization: 82.03 kJ/mol; (17)Boiling Point: 518 °C at 760 mmHg; (18)Vapour Pressure: 2.37E-11 mmHg at 25°C.
In addition, you could convert the following datas into the molecular structure:
(1)SMILES:Cc1c(ccc2c1nc(cc2O)c3nc(cs3)C(C)C)OC
(2)InChI:InChI=1/C17H18N2O2S/c1-9(2)13-8-22-17(19-13)12-7-14(20)11-5-6-15(21-4)10(3)16(11)18-12/h5-9H,1-4H3,(H,18,20)
(3)InChIKey:LPPRPUJPNUYIKH-UHFFFAOYAQ
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