Trifluoroacetic acid → HCID 136232555, compound

HRID 1047549Notes

Reaction equation

HRID 1047549 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]([CH:29]3[CH2:34][CH2:33][N:32]([C:35]4[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=4)[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]([CH:29]3[CH2:30][CH2:31][N:32]([C:35]4[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=4)[CH2:33][CH2:34]3)=[O:28])[CH:24]=2)[NH:19][N:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136352257HCID 136352257, compound

Product 1

HCID 136232555HCID 136232555, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.5 mL, 6.90 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-(pyridin-4-yl)piperidine-4-carboxamide (12 mg, 0.023 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 (7 mg) as an off-white solid. 1H NMR (400 MHz, CD3OD): δ 8.50 (s, 1H), 8.10 (m, 2H), 7.73 (d, 1H, J=8.8 Hz), 7.65 (m, 2H), 7.57 (d, 1H, J=9.2 Hz), 7.27 (m, 2H), 6.94 (m, 2H), 4.17 (m, 2H), 3.11 (m, 2H), 2.77 (m, 1H), 2.03 (m, 2H), 1.89 (m, 2H); ESI-MS [M+2H/2]+: 219.61.

Workup

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

Sources & evidence

ORD record
ord-89c520055bc54d28b6c11317ce9e124f
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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