Trifluoroacetic acid → HCID 136232547, compound

HRID 1047547Notes

Reaction equation

HRID 1047547 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[CH2:32][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]3)=[O:28])[CH:24]=2)[NH:19][N:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136352256HCID 136352256, compound

Product 1

HCID 136232547HCID 136232547, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.5 mL, 7.20 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-cyclopropylurea (10 mg, 0.024 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 (6 mg) as an off-white solid. 1H NMR (400 MHz, CD3OD): δ 8.53 (s, 1H), 7.69-7.67 (m, 2H), 7.59 (d, 1H, J=8.8 Hz), 7.27 (m, 3H), 3.91 (t, 2H, J=5.6 Hz), 3.62 (m, 1H), 2.64 (t, 2H, J=6.0 Hz); ESI-MS [M+H]+: 333.1.

Workup

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

Sources & evidence

ORD record
ord-ba98370006ab43eb9e02b85f39f10af6
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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