Trifluoroacetic acid → N-(3-(1H-benzo[d]imidazol-2-yl)-1H-indazol-5-yl)-1,4-dimethylpiperidine-4-carboxamide

HRID 1047538Notes

Reaction equation

HRID 1047538 reaction equation
C(O)(C(F)(F)F)=O.[NH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([NH:26][C:27]([C:29]3([CH3:36])[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)=[O:28])[CH:24]=2)[N:19](C2CCCCO2)[N:18]=1>C(Cl)Cl>[NH:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]=[C:9]1[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([NH:26][C:27]([C:29]3([CH3:36])[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)=[O:28])[CH:24]=2)[NH:19][N:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136352251N-(3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)-1,4-dimethylpiperidine-4-carboxamide

Product 1

HCID 136232553N-(3-(1H-benzo[d]imidazol-2-yl)-1H-indazol-5-yl)-1,4-dimethylpiperidine-4-carboxamideYield 51.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.1 mL, 1.587 mmol) was added to a solution of N-(3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)-1,4-dimethylpiperidine-4-carboxamide (5 mg, 0.010 mmol) in CH2Cl2 (4 mL). The reaction mixture was stirred at room temperature for 24 h, and then the solvent was removed in vacuo. Purification by flash chromatography (6% CH3OH/CH2Cl2) afforded the title compound (2 mg) as a white solid. 1H NMR (400 MHz, CD3OD): δ 8.49 (bs, 1H), 7.64 (m, 4H), 7.29 (m, 2H), 3.49 (m, 2H), 3.18 (m, 2H), 2.91 (s, 3H), 2.59 (m, 2H), 1.46 (m, 2H), 1.28 (s, 3H); ESI-MS [M+H]+: 389.3.

Workup

  1. customthe solvent was removed in vacuo
  2. customPurification by flash chromatography (6% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-e4f64ab512144be997ccb77e653ca3c7
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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