Trifluoroacetic acid → HCID 178486807, compound

HRID 1009747Notes

Reaction equation

HRID 1009747 reaction equation
C(OC([NH:8][C:9]1[CH:13]=[C:12]([NH:14][C:15](=[O:38])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[C:33]4[C:28](=[CH:29][C:30]([O:36][CH3:37])=[C:31]([O:34][CH3:35])[CH:32]=4)[N:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)[N:11](CC2C=CC(OC)=C(OC)C=2)[N:10]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[NH2:8][C:9]1[CH:13]=[C:12]([NH:14][C:15](=[O:38])[CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24]3[C:33]4[C:28](=[CH:29][C:30]([O:36][CH3:37])=[C:31]([O:34][CH3:35])[CH:32]=4)[N:27]=[CH:26][CH:25]=3)=[CH:21][CH:22]=2)[NH:11][N:10]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67305027HCID 67305027, compound

Product 1

HCID 178486807HCID 178486807, compoundYield 35.9%

Procedure

A mixture of N-[3-(N-tert-butoxycarbonylamino)-1-(3,4-dimethoxybenzyl)pyrazol-5-yl]-2-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]acetamide (0.2 g) and trifluoroacetic acid (5 ml) was stirred at ambient temperature for 2 hours. The resultant mixture was evaporated. The residue was purified by column chromatography on silica using a solvent gradient from 49:1 to 9:1 of methylene chloride and a 3M methanolic ammonia solution as eluent. There was thus obtained the title compound (0.045 g); 1H NMR: (DMSOd6) 3.63 (s, 2H), 3.93 (s, 3H), 3.95 (s, 3H), 5.05 (br s, 2H), 5.58 (s, 1H), 6.5 (d, 1H), 7.23 (d, 2H), 7.41 (s, 1H), 7.45 (d, 2H), 7.51 (s, 1H), 8.5 (d, 1H), 10.35 (br s, 1H); Mass Spectrum: M+H+ 420.

Workup

  1. customThe resultant mixture was evaporated
  2. customThe residue was purified by column chromatography on silica using a solvent gradient from 49:1 to 9:1 of methylene chloride

Sources & evidence

ORD record
ord-f913f058db22468291da50fd10c9353e
Source dataset
uspto-grants-2011_07
Patent number
US07973164B2

Reaction notes

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