Trifluoroacetic acid → HCID 178513585, compound

HRID 1297185Notes

Reaction equation

HRID 1297185 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[NH:27][C:26]3[CH:28]=[CH:29][C:30]([C:32](=[O:34])[NH2:33])=[CH:31][C:25]=3[N:24]=2)=[CH:19][CH:18]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[NH:27][C:26]3[CH:28]=[CH:29][C:30]([C:32]([NH2:33])=[O:34])=[CH:31][C:25]=3[N:24]=2)=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178451835HCID 178451835, compound

Product 1

HCID 178513585HCID 178513585, compoundYield 133.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cold solution of 2-{2-[4-(5-carbamoyl-1H-benzoimidazol-2-yl)-phenoxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (0.65 g, 1.4 mmol) in CH2Cl2 (15 mL) was slowly added TFA (3.8 mL). The solution was stirred and gradually warmed to rt over 2 h. All solvent was removed via toluene azeotrope to provide the 0.68 g (100%) of the product as a yellow solid. HPLC (Method C): Rt=3.87. MS (ESI+): mass calcd. for C21H24N4O2, 364.19; m/z found, 365.1 [M+H]+. 1H NMR (400 MHz, CD3OD): 6.20 (s, 1H), 8.05 (d, J=8.7 Hz, 2H), 7.79 (d, J=10.7 Hz, 1H), 7.73 (d, J=10.7 Hz, 1H), 7.20 (d, J=8.7 Hz, 2H), 4.23-4.19 (m, 2H), 3.31-3.28 (m, 2H), 3:03-2.89 (m, 1H), 2.17-2.11 (m, 1H), 2.10-1.98 (m, 2H), 1.83-1.76 (m, 2H), 1.64-1.44 (m, 3H).

Workup

  1. customAll solvent was removed via toluene

Sources & evidence

ORD record
ord-957e555a877e49fe95364e7c759585a6
Source dataset
uspto-grants-2007_07
Patent number
US07250427B2

Reaction notes

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