3-{4-[2-(4-chloro-phenyl)-7-oxo-7H-thieno[2,3-c]pyridin-6-yl]-phenylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester → (+/-)-Pyrrolidine-3-carboxylic acid {4-[2-(4-chloro-phenyl)-7-oxo-7H-thieno[2,3-c]pyridin-6-yl]-phenyl}-amide

HRID 2384945Notes

Reaction equation

HRID 2384945 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([C:13](=[O:38])[NH:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:26]=[CH:25][C:24]4[CH:27]=[C:28]([C:30]5[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=5)[S:29][C:23]=4[C:22]3=[O:37])=[CH:17][CH:16]=2)[CH2:9]1)=O)(C)(C)C>C(Cl)Cl>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([C:28]2[S:29][C:23]3[C:22](=[O:37])[N:21]([C:18]4[CH:17]=[CH:16][C:15]([NH:14][C:13]([CH:10]5[CH2:11][CH2:12][NH:8][CH2:9]5)=[O:38])=[CH:20][CH:19]=4)[CH:26]=[CH:25][C:24]=3[CH:27]=2)=[CH:31][CH:32]=1

Participants

3

Reactant 1

HCID 689499533-{4-[2-(4-chloro-phenyl)-7-oxo-7H-thieno[2,3-c]pyridin-6-yl]-phenylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86629215(+/-)-Pyrrolidine-3-carboxylic acid {4-[2-(4-chloro-phenyl)-7-oxo-7H-thieno[2,3-c]pyridin-6-yl]-phenyl}-amideYield 889%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add trifluoroacetic (1.06 mL, 14.1 mmol) to a solution of 3-{4-[2-(4-chloro-phenyl)-7-oxo-7H-thieno[2,3-c]pyridin-6-yl]-phenylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (0.12 g, 0.21 mmol) in CH2Cl2 (2 mL). Stir the mixture at RT for 2 h, and concentrate in vacuo. Dissolve the crude residue in CH2Cl2, filter through an SCX column with CH2Cl2 and MeOH, then elute the product with 2 N NH3 in MeOH. Concentrate the solution, then filter the solid with Et2O to give 0.84 g (88%) of the title compound. LC-ES/MS m/z (35Cl) 450.0 [M+H]+.

Workup

  1. concentrationconcentrate in vacuo
  2. dissolutionDissolve the crude residue in CH2Cl2
  3. filtrationfilter through an SCX column with CH2Cl2 and MeOH
  4. washelute the product with 2 N NH3 in MeOH
  5. concentrationConcentrate the solution
  6. filtrationfilter the solid with Et2O

Sources & evidence

ORD record
ord-70c447cb77aa4dd1839593d77faf0576
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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