Trifluoroacetic acid → HCID 178483561, compound

HRID 2274400Notes

Reaction equation

FC(F)(F)C(O)=O.[CH3:8][N:9]([CH3:44])[CH2:10][CH2:11][CH2:12][O:13][C:14]1[C:15]([F:43])=[CH:16][C:17]2[N:21]=[C:20]([C:22]3[C:26]([NH:27][C:28]([N:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[O:29])=[CH:25][N:24](C4CCCCO4)[N:23]=3)[NH:19][C:18]=2[CH:42]=1>ClCCl>[CH3:44][N:9]([CH3:8])[CH2:10][CH2:11][CH2:12][O:13][C:14]1[C:15]([F:43])=[CH:16][C:17]2[N:21]=[C:20]([C:22]3[C:26]([NH:27][C:28]([N:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)=[O:29])=[CH:25][NH:24][N:23]=3)[NH:19][C:18]=2[CH:42]=1

Participants

Conditions

Temperature: 22 °C

Procedure

0.5 mL of trifluoroacetic acid is added to a solution of 28 mg of piperidine-1-carboxylic acid [3-[6-(3-dimethylaminopropoxy)-5-fluoro-1H-benzimidazol-2-yl]-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]amide in solution in 1.5 mL of dichloromethane. The reaction medium is stirred at 22° C. for 16 hours. The reaction medium is concentrated under reduced pressure in a rotary evaporator, taken up several times with isopropyl ether and concentrated under reduced pressure in a rotary evaporator each time. 40 mg of N-{3-[6-(3-dimethylaminopropoxy)-5-fluoro-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl}piperidine-1-carboxamide are obtained in the form of trifluoroacetic acid salt. 1H NMR (300 MHz, DMSO-d6, δ in ppm): 1.47 to 1.72 (m, 6H); 2.19 (m, 2H); 2.84 (s, 6H); 3.27 (m, 2H); 3.42 (m, 4H); 4.22 (t, J=6.0 Hz, 2H); 7.40 (d, J=7.5 Hz, 1H); 7.65 (d, J=10.0 Hz, 1H); 8.00 (s, 1H).

Workup

concentrationThe reaction medium is concentrated under reduced pressure in a rotary evaporator
concentrationconcentrated under reduced pressure in a rotary evaporator each time

Sources & evidence

ORD record: ord-4f882fbc602b4944bc96d85d485f30a3
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126969B2

Reaction notes

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