Methanol → 4-Cyano-1h-pyrrole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt

HRID 1992040Notes

Reaction equation

HRID 1992040 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[NH:24][CH:25]=[C:26]([C:28]#[N:29])[CH:27]=3)=[O:22])=[C:16]([C:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37].CO>C(Cl)Cl.CO>[F:39][C:38]([F:41])([F:40])[C:36]([OH:42])=[O:37].[C:30]1([C:16]2[CH:15]=[C:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)[CH:19]=[CH:18][C:17]=2[NH:20][C:21]([C:23]2[NH:24][CH:25]=[C:26]([C:28]#[N:29])[CH:27]=2)=[O:22])[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 586945824-{4-[(4-Cyano-1H-pyrrole-2-carbonyl)-amino]-3-cyclohex-1-enyl-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 116055404-Cyano-1h-pyrrole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid saltYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 36.0 mg (0.0759 mmol) 4-{4-[(4-cyano-1H-pyrrole-2-carbonyl)-amino]-3-cyclohex-1-enyl-phenyl}-piperidine-1-carboxylic acid tert-butyl ester (as prepared in the previous step) in 5 mL CH2Cl2 was treated with 4 drops MeOH and 1 mL TFA and stirred at RT for 2 h. MeOH (5 mL) was added, and solvents were evaporated in vacuo. Purification of the residue by RP-HPLC (C18) with 10-80% CH3CN in 0.1% TFA/H2O over 30 min afforded 22.0 mg (59%) of the title compound as a white solid: Mass spectrum (ESI, m/z): Calcd. for C23H26N4O, 375.2 (M+H), found 375.2.

Workup

  1. customsolvents were evaporated in vacuo
  2. customPurification of the residue by RP-HPLC (C18) with 10-80% CH3CN in 0.1% TFA/H2O over 30 min

Sources & evidence

ORD record
ord-b1eac0056db14cf39003843268d5d464
Source dataset
uspto-grants-2010_01
Patent number
US07645755B2

Reaction notes

Loading…