Water → tert-butyl (3S,5R)-3-{[(7-chlorothieno[3,2-b]pyridin-6-yl)carbonyl](2-methylpropyl)amino}-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate

HRID 2192866Notes

Reaction equation

HRID 2192866 reaction equation
[CH3:1][CH:2]([CH3:26])[CH2:3][NH:4][C@H:5]1[CH2:10][C@@H:9]([C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[O:12])[CH2:8][N:7]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:6]1.C(N(C(C)C)CC)(C)C.[Cl:36][C:37]1[C:42]([C:43](Cl)=[O:44])=[CH:41][N:40]=[C:39]2[CH:46]=[CH:47][S:48][C:38]=12.O>ClCCl>[Cl:36][C:37]1[C:42]([C:43]([N:4]([CH2:3][CH:2]([CH3:26])[CH3:1])[C@H:5]2[CH2:10][C@@H:9]([C:11]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[O:12])[CH2:8][N:7]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:6]2)=[O:44])=[CH:41][N:40]=[C:39]2[CH:46]=[CH:47][S:48][C:38]=12

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 59356577tert-Butyl (3S,5R)-3-(isobutylamino)-5-(morpholine-4-carbonyl)piperidine-1-carboxylateHCID 866492997-Chlorothieno[3,2-b]pyridine-6-carbonyl chloride

Product 1

HCID 59625380tert-butyl (3S,5R)-3-{[(7-chlorothieno[3,2-b]pyridin-6-yl)carbonyl](2-methylpropyl)amino}-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylateYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl (3S,5R)-3-[(2-methylpropyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate (100 mg) and diisopropylethylamine (0.095 ml) were dissolved in dichloromethane (3 ml), a solution of 7-chlorothieno[3,2-b]pyridine-6-carbonyl chloride (70 mg) in dichloromethane (2 ml) was added dropwise, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate was concentrated under reduced pressure to give the object compound (120 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. washthe fraction eluted with ethyl acetate
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-a7705331e6564f69a059ead2c35660f9
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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