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inquiry17β-[(N,N-dimethylcarbamoyl)thio]formyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-one androstone-1,4-diene
17-propionate carbothioic acid
Conditions | Yield |
---|---|
Stage #1: 17β-[(N,N-dimethylcarbamoyl)thio]formyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-one androstone-1,4-diene With methanol; potassium carbonate at 20℃; for 5 - 7h; Stage #2: With hydrogenchloride In water at 20℃; pH=1.5 - 2.0; Product distribution / selectivity; | 96.33% |
With calcium hydroxide In methanol at 25 - 30℃; for 24h; Reagent/catalyst; | 96.3% |
With potassium carbonate In methanol at 25℃; for 5h; Inert atmosphere; | 95% |
propionyl chloride
6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carbothioic acid
17-propionate carbothioic acid
Conditions | Yield |
---|---|
Stage #1: propionyl chloride; 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carbothioic acid With triethylamine In dichloromethane at -5℃; Stage #2: With diethylamine In acetone for 1h; regioselective reaction; | 91% |
With pyridine In acetone at -20 - -15℃; Product distribution / selectivity; | 88% |
With 1-methyl-1H-imidazole In acetone at -20 - -15℃; Product distribution / selectivity; | 88% |
6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid
17-propionate carbothioic acid
Conditions | Yield |
---|---|
Stage #1: 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid With 1-methyl-1H-imidazole In ISOPROPYLAMIDE at 50℃; Stage #2: With sodium hydrogensulfide In ISOPROPYLAMIDE at 35℃; for 0.25h; Stage #3: With hydrogenchloride In ISOPROPYLAMIDE; water pH=2; | 32% |
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 20 °C 2: Et2NH / Heating View Scheme | |
Multi-step reaction with 2 steps 1: sodium iodide; triethylamine / tetrahydrofuran / 4 h / 70 - 75 °C 2: morpholine / 3 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: triethylamine; sodium iodide / acetone; water / 6 h / 10 - 30 °C 1.2: 1 h / 0 °C 2.1: potassium carbonate / methanol / 5 h / 25 °C / Inert atmosphere View Scheme |
Propionic acid (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-propionylsulfanylcarbonyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester
17-propionate carbothioic acid
Conditions | Yield |
---|---|
With diethylamine In acetone for 1h; Yield given; |
C24H29F2O5S(1-)*K(1+)
17-propionate carbothioic acid
Conditions | Yield |
---|---|
With hydrogenchloride; water In methanol at 20℃; pH=1 - 2; |
6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carbothioic acid
17-propionate carbothioic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 0.75 h 2: Et2NH / acetone / 1 h View Scheme |
6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid
17-propionate carbothioic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: dimethylformamide / 4 h / Ambient temperature 2: H2S / dimethylformamide 3: Et3N / CH2Cl2 / 0.75 h 4: Et2NH / acetone / 1 h View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / acetone / 3 h / 0 - 5 °C 1.2: 2.5 h / 40 - 45 °C 2.1: sodium iodide; triethylamine / tetrahydrofuran / 4 h / 70 - 75 °C 3.1: morpholine / 3 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / acetone / 4 h / 10 - 25 °C 1.2: 10 - 25 °C 1.3: 0 °C / pH 1 - 1.5 2.1: triethylamine; sodium iodide / acetone; water / 6 h / 10 - 30 °C 2.2: 1 h / 0 °C 3.1: potassium carbonate / methanol / 5 h / 25 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / acetone / 1 h / 0 - 10 °C 1.2: 2 h 2.1: sodium iodide; triethylamine / tetrahydrofuran / 16 h / 20 °C 3.1: calcium hydroxide / methanol / 24 h / 25 - 30 °C View Scheme |
17-propionate carbothioic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2S / dimethylformamide 2: Et3N / CH2Cl2 / 0.75 h 3: Et2NH / acetone / 1 h View Scheme |
17-propionate carbothioic acid
Conditions | Yield |
---|---|
With sodium hydrogensulfide In ISOPROPYLAMIDE at 35℃; for 0.25h; |
17β-[(N,N-dimethylcarbamoyl)thio]formyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-one androstone-1,4-diene
A
methyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carboxylate
B
17-propionate carbothioic acid
Conditions | Yield |
---|---|
With methanol; potassium carbonate at 20℃; for 1 - 5h; Product distribution / selectivity; | |
With methanol; caesium carbonate at 20℃; for 1 - 5h; Product distribution / selectivity; |
propionyl chloride
diethylamine
6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carbothioic acid
17-propionate carbothioic acid
Conditions | Yield |
---|---|
With triethylamine In dichloromethane; ethyl acetate; acetone |
propanethioic acid
6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid
17-propionate carbothioic acid
Conditions | Yield |
---|---|
Stage #1: 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 5℃; for 18h; Inert atmosphere; Stage #2: propanethioic acid In tetrahydrofuran at 5 - 25℃; for 7h; Product distribution / selectivity; Inert atmosphere; |
flumetasone
17-propionate carbothioic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium periodate / water; tetrahydrofuran / 2 h / 25 - 30 °C 2.1: triethylamine / acetone / 3 h / 0 - 5 °C 2.2: 2.5 h / 40 - 45 °C 3.1: sodium iodide; triethylamine / tetrahydrofuran / 4 h / 70 - 75 °C 4.1: morpholine / 3 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: periodic acid / water; tetrahydrofuran / 2 h / 0 - 10 °C 2.1: triethylamine / acetone / 1 h / 0 - 10 °C 2.2: 2 h 3.1: sodium iodide; triethylamine / tetrahydrofuran / 16 h / 20 °C 4.1: calcium hydroxide / methanol / 24 h / 25 - 30 °C View Scheme |
17-propionate carbothioic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium hypobromide / 1,4-dioxane / 5 h / 8 °C 2.1: triethylamine / acetone / 4 h / 10 - 25 °C 2.2: 10 - 25 °C 2.3: 0 °C / pH 1 - 1.5 3.1: triethylamine; sodium iodide / acetone; water / 6 h / 10 - 30 °C 3.2: 1 h / 0 °C 4.1: potassium carbonate / methanol / 5 h / 25 °C / Inert atmosphere View Scheme |
bromoacetic acid
17-propionate carbothioic acid
6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxoandrosta-1,4-diene-17β-carbothioate
Conditions | Yield |
---|---|
Stage #1: bromoacetic acid; 17-propionate carbothioic acid With triethylamine In acetone at 25℃; for 5h; Stage #2: With hydrogenchloride In water; acetone at 0℃; pH=1 - 1.5; | 97.1% |
With triethylamine In dichloromethane at 20℃; |
17-propionate carbothioic acid
6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbonylsulfenic acid
Conditions | Yield |
---|---|
With water; urea In methanol at 10 - 15℃; for 1h; | 96.22% |
With dihydrogen peroxide In methanol at 10 - 20℃; for 1h; | 96.22% |
Conditions | Yield |
---|---|
With potassium hydrogencarbonate In N,N-dimethyl-formamide at -10 - 20℃; for 2h; | 91.7% |
With potassium carbonate In acetone at -5 - 0℃; for 2 - 5h; Product distribution / selectivity; | 84.51% |
Stage #1: 17-propionate carbothioic acid With potassium carbonate In acetone at 20℃; for 0.5h; Stage #2: bromofluoromethane In acetone at 0 - 5℃; | 80% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; for 6h; chemoselective reaction; | 82% |
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 22 - 25℃; for 0.25h; | 67.1% |
With potassium carbonate; sodium hydrogensulfite In acetone at -10℃; |
N-ethyl-N,N-diisopropylamine
17-propionate carbothioic acid
Conditions | Yield |
---|---|
In isopropyl alcohol at 5 - 25℃; for 3.25h; | 82% |
In isopropyl alcohol at 5 - 25℃; for 3.25h; | 82% |
chlorobromomethane
17-propionate carbothioic acid
S-chloromethyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In N,N-dimethyl acetamide for 2h; | 67% |
Stage #1: 17-propionate carbothioic acid With sodium hydrogencarbonate In acetonitrile at 5℃; for 0.5h; Stage #2: chlorobromomethane In acetonitrile at 5 - 25℃; for 12h; |
17-propionate carbothioic acid
Conditions | Yield |
---|---|
Stage #1: (10-bromodecyl)phosphonic acid; 17-propionate carbothioic acid In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 63% |
Stage #1: (10-bromodecyl)phosphonic acid; 17-propionate carbothioic acid at 25℃; for 0.166667h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine at 25℃; Inert atmosphere; | 63% |
17-propionate carbothioic acid
17,17'-(trisulfanediyldicarbonyl)bis(6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxoandrosta-17α-yl) dipropanoate
Conditions | Yield |
---|---|
With thioacetic acid S-ethoxydisulfanyl ester In tetrachloromethane; dichloromethane for 8h; Reflux; | 42% |
4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one
17-propionate carbothioic acid
Conditions | Yield |
---|---|
With potassium carbonate In diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide | 27% |
2-buten-4-olide
17-propionate carbothioic acid
Conditions | Yield |
---|---|
With potassium carbonate In ethyl acetate; N,N-dimethyl-formamide | 3% |
17-propionate carbothioic acid
[18F]fluoromethylene toluene-4-sulfonate
Conditions | Yield |
---|---|
In acetonitrile at 110℃; for 0.333333h; | |
With potassium carbonate In acetonitrile at 110℃; for 0.75h; |
17-propionate carbothioic acid
flixotide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 67 percent / NaHCO3 / N,N-dimethyl-acetamide / 2 h 2: 85 percent / NaI / acetone / Heating 3: 74 percent / AgF / acetonitrile / 4 h / Ambient temperature View Scheme | |
Multi-step reaction with 5 steps 1: triethylamine / dichloromethane / 3 h / 20 °C 2: triethylamine / dmap / tetrahydrofuran / 20 °C 3: trifluoroacetic acid / 2 h / 20 °C 4: xenon fluoride / dichloromethane / 48 h / -10 °C 5: ammonia; methanol / 0.08 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1: triethylamine / dichloromethane / 3 h / 20 °C 2: triethylamine; dmap / tetrahydrofuran / 20 °C 3: trifluoroacetic acid / 2 h / 20 °C 4: xenon difluoride / dichloromethane / 48 h / -10 °C 5: ammonia / methanol / 0.08 h / 0 °C View Scheme |
17-propionate carbothioic acid
S-iodomethyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxo-androsta-1,4-diene-17β-carbothioate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 67 percent / NaHCO3 / N,N-dimethyl-acetamide / 2 h 2: 85 percent / NaI / acetone / Heating View Scheme |
formaldehyd
17-propionate carbothioic acid
S-hydroxymethyl 6α,9α-difluoro-16α-methyl-3-oxo-11β-hydroxy-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate
Conditions | Yield |
---|---|
In dichloromethane; water at 0℃; for 1h; |
Conditions | Yield |
---|---|
base; | |
With potassium thiosulfate; 2-methylacrylic acid 3-hydroxypropyl ester at 10℃; |
morpholine
N-methylcyclohexylamine
cyclohexylamine
diethylamine
triethylamine
N-cyclohexyl-cyclohexanamine
17-propionate carbothioic acid
Conditions | Yield |
---|---|
Combinatorial reaction / High throughput screening (HTS); |
α-methylene-γ-butyrolactone
17-propionate carbothioic acid
6α,9α-Difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxy-androsta-1,4-diene-17β-carbothioic acid S-(2-oxo-tetrahydro-furan-3-ylmethyl) ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide |
α-bromo-γ-butyrolactone
17-propionate carbothioic acid
6α,9α-Difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxy-androsta-1,4-diene-17β-carbothioic acid S-(2-oxo-tetrahydro-furan-3-yl) ester
Conditions | Yield |
---|---|
With potassium carbonate In ethyl acetate; N,N-dimethyl-formamide |
2-bromo-1-tetralone
17-propionate carbothioic acid
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 25 - 30℃; for 3h; |
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