Trifluoroacetic acid → HCID 178522440, compound

HRID 1012121Notes

Reaction equation

HRID 1012121 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:40]=[CH:39][C:19]3[NH:20][C:21]([C:23]4[C:27]([NH:28][C:29](=[O:38])[C:30]5[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:31]=5[F:37])=[CH:26][NH:25][N:24]=4)=[N:22][C:18]=3[CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:37][C:31]1[CH:32]=[CH:33][CH:34]=[C:35]([F:36])[C:30]=1[C:29]([NH:28][C:27]1[C:23]([C:21]2[NH:20][C:19]3[CH:39]=[CH:40][C:16]([O:15][CH2:14][CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)=[CH:17][C:18]=3[N:22]=2)=[N:24][NH:25][CH:26]=1)=[O:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178451987HCID 178451987, compound

Product 1

HCID 178522440HCID 178522440, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{2-[4-(2,6-Difluoro-benzoylamino)-1H-pyrazol-3-yl]-1H-benzimidazol-5-yloxymethyl}-piperidine-1-carboxylic acid tert-butyl ester (0.024 g, 0.043 mmol) (prepared in a manner analogous to Example 130) was treated with 1:1 TFA:DCM (2 ml) for 20 min. The solution was reduced in vacuo and azeotroped with toluene (×3). Purification by preparative LC/MS gave 2,6-difluoro-N-{3-[5-(piperidin-4-ylmethoxy)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl}-benzamide as a white solid (8 mg, 41%). (LC/MS: Rt 1.99, [M+H]+ 453.06).

Workup

  1. customazeotroped with toluene (×3)
  2. customPurification by preparative LC/MS

Sources & evidence

ORD record
ord-cc17134e7c7441ada822b22802336a06
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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