Trifluoroacetic acid → SB-747651A

HRID 1394201Notes

Reaction equation

HRID 1394201 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[C:17]3[N:24]([CH2:25][CH3:26])[C:23]([C:27]4[C:31]([NH2:32])=[N:30][O:29][N:28]=4)=[N:22][C:18]=3[CH:19]=[N:20][CH:21]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.CO>[NH2:32][C:31]1[C:27]([C:23]2[N:24]([CH2:25][CH3:26])[C:17]3[C:16]([CH2:15][NH:14][CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)=[CH:21][N:20]=[CH:19][C:18]=3[N:22]=2)=[N:28][O:29][N:30]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 691594734-{[2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-7-ylmethyl]-amino}-piperidine-1-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 11393719SB-747651AYield 91.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the product from Step 2 (0.075 g, 0.17 mmol) in dichoromethane (1 ml) was treated with trifluoroacetic acid (1 ml). After 2 hours the reaction was reduced in vacuo, dissolved in methanol and applied to a SCX ion exchange column and eluted with methanol and then a mixture of methanol/0.880 ammonia (9:1). The basic fractions were then reduced to afford the title compound, (0.053 g, 91%); MS (ES+) m/e 343 [M+H]+.

Workup

  1. washeluted with methanol
  2. additiona mixture of methanol/0.880 ammonia (9:1)

Sources & evidence

ORD record
ord-992f026bf4e749b4bf67e209e35ee839
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

Loading…