Trifluoroacetic acid → HCID 178521828, compound

HRID 1047568Notes

Reaction equation

HRID 1047568 reaction equation
C(O)(C(F)(F)F)=O.[O:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:43]=[CH:42][C:17]3[NH:18][C:19]([C:21]4[C:29]5[C:24](=[CH:25][CH:26]=[C:27]([NH:30][C:31]([CH:33]6[CH2:35][CH2:34]6)=[O:32])[CH:28]=5)[N:23](C5CCCCO5)[N:22]=4)=[N:20][C:16]=3[CH:15]=2)[CH2:10][CH2:9]1>C(Cl)Cl>[O:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:43]=[CH:42][C:17]3[NH:18][C:19]([C:21]4[C:29]5[C:24](=[CH:25][CH:26]=[C:27]([NH:30][C:31]([CH:33]6[CH2:34][CH2:35]6)=[O:32])[CH:28]=5)[NH:23][N:22]=4)=[N:20][C:16]=3[CH:15]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178521726HCID 178521726, compound

Product 1

HCID 178521828HCID 178521828, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.238 mL, 3.08 mmol) was added to solution of N-(3-(5-morpholino-1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)cyclopropanecarboxamide (15 mg, 0.031 mmol) in CH2Cl2 (5 mL). The reaction mixture was stirred overnight at room temperature, and then the solvent was removed in vacuum. Purification by flash column chromatography (5% CH3OH/CH2Cl2) afforded the title compound (10 mg) as a solid. 1H NMR: (400 MHz, CD3OD): δ 8.59 (d, 1H, J=1.2 Hz), 7.66 (m, 2H), 7.47 (dd, 1H, J=1.6 and 9.2 Hz), 7.31 (dd, 1H, J=2.0 and 9.2 Hz), 7.16 (s, 1H), 3.87 (m, 4H), 3.23 (m, 4H), 1.85 (m, 1H), 1.03 (m, 2H), 0.93 (m, 2H); ESI-MS [M+H]+: 403.19.

Workup

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

Sources & evidence

ORD record
ord-d3001b8fcd6444a7816f447221eb5b1b
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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