Trifluoroacetic acid → HCID 136232554, compound

HRID 1047545Notes

Reaction equation

HRID 1047545 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]([NH:29][CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]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]([NH:29][CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34]3)=[O:28])[CH:24]=2)[NH:19][N:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136352255HCID 136352255, compound

Product 1

HCID 136232554HCID 136232554, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.3 mL, 4.03 mmol) was added to a solution of 1-(3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)-3-cyclopentylurea (6 mg, 0.013 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 (4 mg) as an off-white solid. 1H NMR (400 MHz, CD3OD): δ 8.36 (s, 1H), 7.81 (m, 2H), 7.60 (d, 1H, J=8.8 Hz), 7.46 (m, 3H), 4.11 (t, 1H, J=6.4 Hz), 2.00 (m, 2H), 1.75 (m, 2H), 1.65 (m, 2H), 1.51 (m, 2H); ESI-MS [M+H]+: 361.3.

Workup

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

Sources & evidence

ORD record
ord-32ebda5d593b45e5a747ec072a9b37e2
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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