Trifluoroacetic acid → HCID 131726503, compound

HRID 216455Notes

Reaction equation

HRID 216455 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:22]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][C:25]=2[Cl:31])=[C:21]([F:32])[C:8]2[N:9]=[CH:10][N:11]([CH2:12][CH2:13][C:14]([O:16]C(C)(C)C)=[O:15])[C:7]=2[CH:6]=1)=[O:4].[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34]>C(Cl)Cl>[OH:39][C:33]([C:35]([F:38])([F:37])[F:36])=[O:34].[CH3:1][O:2][C:3]([C:5]1[C:22]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][C:25]=2[Cl:31])=[C:21]([F:32])[C:8]2[N:9]=[CH:10][N:11]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])[C:7]=2[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 668866626-(4-Bromo-2-chloro-phenylamino)-3-(2-tert-butoxycarbonyl-ethyl)-7-fluoro-3H-benzoimidazole-5-carboxylic acid methyl ester

Product 1

HCID 131726503HCID 131726503, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(4-Bromo-2-chloro-phenylamino)-3-(2-tert-butoxycarbonyl-ethyl)-7-fluoro-3H-benzoimidazole-5-carboxylic acid methyl ester (0.050 g, 0.095 mmol) is dissolved in methylene chloride (0.5 mL) and TFA (0.5 mL) is added. After 45 minutes, the reaction mixture is concentrated to dryness to give 0.49 g (88%)desired product: LC/MS ESI (+) m/z 472, 470 (M+ Br pattern) detected; 1H NMR (400 MHz, DMSO-d6) δ 8.51 (s, 1H), 8.20 (s, 1H), 8.13 (s, 1H), 7.64 (d, 1H), 7.29 (dd, 1H), 6.45 (dd, 1H), 4.55 (t, 2H), 2.89 (t, 2H).

Workup

  1. concentrationthe reaction mixture is concentrated to dryness

Sources & evidence

ORD record
ord-5f45551e6d3448b990194a0dc311d043
Source dataset
uspto-grants-2012_06
Patent number
US08193229B2

Reaction notes

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