Trifluoroacetic acid → HCID 136232543, compound

HRID 1047566Notes

Reaction equation

HRID 1047566 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[CH2:31][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]3)=[O:28])[CH:24]=2)[NH:19][N:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136352265HCID 136352265, compound

Product 1

HCID 136232543HCID 136232543, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (568 mg, 4.98 mmol) was added to solution of N-(3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)cyclopropanecarboxamide (20 mg, 0.050 mmol) in CH2Cl2 (5 mL). The reaction mixture was stirred overnight at room temperature, and then the solvent was removed in vacuo. Purification by flash column chromatography (5% CH3OH/CH2Cl2) afforded the title compound (10 mg) as a pale yellow solid. 1H NMR: (400 MHz, CD3OD): δ 8.63 (s, 1H), 7.80 (m, 2H), 7.68 (d, 1H, J=9.2 Hz), 7.57 (m 2H), 7.49 (d, 1H, J=8.8 Hz), 1.85 (m, 1H), 1.03 (m, 2H), 0.92 (m, 2H); ESI-MS [M+H]+: 318.06.

Workup

  1. customthe solvent was removed in vacuo
  2. customPurification by flash column chromatography (5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-74025debb326487fb2d7b4f4e5a1af54
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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