HCID 69060862, compound → HCID 178424556, compound

HRID 1723867Notes

Reaction equation

HRID 1723867 reaction equation
C([N:5]1[C:9]([NH:10][C:11]([C:13]2[CH:28]=[CH:27][C:16]3[N:17]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=4)[CH:18]=[N:19][C:15]=3[CH:14]=2)=[O:12])=[CH:8][C:7]([C:29]2[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=2)=[N:6]1)(C)(C)C>C(O)=O>[C:31]1([CH3:35])[CH:32]=[CH:33][CH:34]=[C:29]([C:7]2[CH:8]=[C:9]([NH:10][C:11]([C:13]3[CH:28]=[CH:27][C:16]4[N:17]([C:20]5[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=5)[CH:18]=[N:19][C:15]=4[CH:14]=3)=[O:12])[NH:5][N:6]=2)[CH:30]=1

Participants

3

Reactant 1

HCID 69060862HCID 69060862, compound

Product 1

HCID 178424556HCID 178424556, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

General procedure for t-butyl cleavage: N-(2-tert-butyl-5-m-tolyl-2H-pyrazol-3-yl) 1-(3-Fluoro-phenyl)-1H-benzimidazole-5-carboxamide (110 mg, 0.235 mmol) was dissolved in formic acid (3 mL) and the mixture stirred at reflux for 30 min. The solvent was then evaporated and chased with CHCl3 and Et2O and the residue triturated with MeOH. The resulting precipitate was filtered off and washed with MeOH and CHCl3 to give N-(5-m-tolyl-2H-pyrazol-3-yl) 1-(3-fluorophenyl)-1H-benzimidazole-5-carboxamide: 1H NMR (400 MHz, CDCl3) δ 2.55 (s, 3H), 7.05 (br.s, 1H), 7.18 (br.d, J=8.4 Hz, 1H), 7.33-7.43 (m, 2H), 7.57 (br.d, J=7.6 Hz, 1H), 7.62 (br.d, J=8.0 Hz, 2H), 7.70-7.74 (m, 2H), 7.78 (d, J=8.4 Hz, 1H), 8.07 (dd, J=8.0 Hz, J=2.0 Hz, 1H), 8.54 (s, 1H), 8.75 (s, 1H); MS (ES+): m/z 412 [MH+].

Workup

  1. temperatureat reflux for 30 min
  2. customThe solvent was then evaporated
  3. customthe residue triturated with MeOH
  4. filtrationThe resulting precipitate was filtered off
  5. washwashed with MeOH and CHCl3

Sources & evidence

ORD record
ord-5568cec7b8aa48ddaac7e1015f023f1d
Source dataset
uspto-grants-2009_02
Patent number
US07485658B2

Reaction notes

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