Trifluoroacetic acid → 3-{4-[Methyl-(1-methyl-2-phenylamino-1H-benzoimidazol-5-yl)-amino]-pyrimidin-2-ylamino}-benzenesulfonamide trifluoroacetic acid

HRID 1391605Notes

Reaction equation

HRID 1391605 reaction equation
Cl.C(OC(=O)[N:8]([C:15]1[N:19]([CH3:20])[C:18]2[CH:21]=[CH:22][C:23]([N:25]([CH3:43])[C:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([S:39](=[O:42])(=[O:41])[NH2:40])[CH:34]=4)[N:27]=3)=[CH:24][C:17]=2[N:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(C)(C)C.[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48]>C(Cl)Cl>[F:45][C:46]([F:51])([F:50])[C:47]([OH:49])=[O:48].[CH3:43][N:25]([C:23]1[CH:22]=[CH:21][C:18]2[N:19]([CH3:20])[C:15]([NH:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N:16][C:17]=2[CH:24]=1)[C:26]1[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C:33]2[CH:34]=[C:35]([S:39]([NH2:40])(=[O:42])=[O:41])[CH:36]=[CH:37][CH:38]=2)[N:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10153410(1-Methyl-5-(methyl-[2-(3-sulfamoyl-phenylamino)-pyrimidin-4-yl]-amino}-1H-benzoimidazol-2-yl)-phenyl-carbamic acid tert-butyl ester hydrochloride

Product 1

HCID 101533173-{4-[Methyl-(1-methyl-2-phenylamino-1H-benzoimidazol-5-yl)-amino]-pyrimidin-2-ylamino}-benzenesulfonamide trifluoroacetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1-Methyl-5-{methyl-[2-(3-sulfamoyl-phenylamino)-pyrimidin-4-yl]-amino}-1H-benzoimidazol-2-yl)-phenyl-carbamic acid tert-butyl ester hydrochloride was stirred in solution of 50% trifluoroacetic acid and methylene chloride and concentrated to give the title compound as a white solid. 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ 10.32 (br s, 1H), 9.54 (br s, 1H), 8.49 (s, 1H), 7.86 (d, J=6.9 Hz, 1H), 7.73-7.78 (m, 3H), 7.47-7.54 (m, 3H), 7.34-7.41 (m, 4H), 7.06-7.14 (m, m 2H), 5.80 (d, J=6.6 Hz, 1H), 3.78 (s, 3H), 3.53 (s, 3H). MS (ESI) m/z=501 [M+H]+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-58680de8d21543d8b968d50dc5836923
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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