4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}-3-[({6-[2,6-difluoro-4-(methylsulfinyl)phenyl]-5-fluoropyridin-2-yl}carbonyl)amino]-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate

Base Information

• Chemical Name: 4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}-3-[({6-[2,6-difluoro-4-(methylsulfinyl)phenyl]-5-fluoropyridin-2-yl}carbonyl)amino]-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate
• CAS No.: 1620013-35-5
• Molecular Formula: C₃₄H₃₈F₃N₅O₆S
• Molecular Weight: 701.767
• Mol file: 1620013-35-5.mol

Synonyms:4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}-3-[({6-[2,6-difluoro-4-(methylsulfinyl)phenyl]-5-fluoropyridin-2-yl}carbonyl)amino]-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate

Chemical Property of 4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}-3-[({6-[2,6-difluoro-4-(methylsulfinyl)phenyl]-5-fluoropyridin-2-yl}carbonyl)amino]-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}-3-[({6-[2,6-difluoro-4-(methylsulfinyl)phenyl]-5-fluoropyridin-2-yl}carbonyl)amino]-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate

There total 24 articles about 4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}-3-[({6-[2,6-difluoro-4-(methylsulfinyl)phenyl]-5-fluoropyridin-2-yl}carbonyl)amino]-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 17.0%

6-[2,6-difluoro-4-(methylsulfinyl)phenyl]-5-fluoropyridine-2-carboxylic acid (1395985-74-6) + 3-amino-4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate (1620012-66-9) → 4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}-3-[({6-[2,6-difluoro-4-(methylsulfinyl)phenyl]-5-fluoropyridin-2-yl}carbonyl)amino]-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate (1620013-35-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 - 30 ℃; for 16h;

Reference yield:

(S)-5-oxopyrrolidine-2-carbonyl chloride (74936-93-9) → 4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}-3-[({6-[2,6-difluoro-4-(methylsulfinyl)phenyl]-5-fluoropyridin-2-yl}carbonyl)amino]-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate (1620013-35-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: dmap; triethylamine / ethyl acetate / 2 h / 20 - 30 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

2.2: 16 h / -78 - 30 °C

3.1: sodium tetrahydroborate / ethanol; tetrahydrofuran / 16 h / -10 - 30 °C

4.1: triethylamine / dichloromethane / 1 h / 0 °C

5.1: 18 h / 70 °C

6.1: hydrogen; palladium 10% on activated carbon / methanol / 15 h / 20 - 30 °C / 760.05 Torr

7.1: triethylamine / isopropyl alcohol / 0.67 h / 100 °C

8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 30 °C

9.1: 0.5 h / 90 °C / Sealed tube

10.1: iron; acetic acid / 3 h / 20 - 30 °C

11.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 - 30 °C

With dmap; sodium tetrahydroborate; palladium 10% on activated carbon; hydrogen; iron; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol;

Reference yield:

(2S,4R)-methanesulfonic acid 2-tert-butoxycarbonylamino-5-methanesulfonyloxy-4-methyl-pentyl ester (1203651-05-1) → 4-{(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-methylpiperidin-1-yl}-3-[({6-[2,6-difluoro-4-(methylsulfinyl)phenyl]-5-fluoropyridin-2-yl}carbonyl)amino]-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate (1620013-35-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 18 h / 70 °C

2: hydrogen; palladium 10% on activated carbon / methanol / 15 h / 20 - 30 °C / 760.05 Torr

3: triethylamine / isopropyl alcohol / 0.67 h / 100 °C

4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 - 30 °C

5: 0.5 h / 90 °C / Sealed tube

6: iron; acetic acid / 3 h / 20 - 30 °C

7: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 - 30 °C

With palladium 10% on activated carbon; hydrogen; iron; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

upstream raw materials:

(S)-5-oxopyrrolidine-2-carbonyl chloride

(2S,4R)-methanesulfonic acid 2-tert-butoxycarbonylamino-5-methanesulfonyloxy-4-methyl-pentyl ester

2,3-cyclopentenopyridine

6,7-dihydro-5H-cyclopenta[b]pyridine 1-oxide

Downstream raw materials:

N-{4-[(3S,5R)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-3-yl}-6-[2,6-difluoro-4-(methylsulfinyl)phenyl]-5-fluoropyridine-2-carboxamide

C₃₂H₃₆F₃N₅O₅S