HCID 18355035, compound → HCID 18354952, compound

HRID 429682Notes

Reaction equation

HRID 429682 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[NH:28][C:29]([C:31]1[C:39]2[N:38]=[C:37]([CH2:40][NH:41]C(OC(C)(C)C)=O)[NH:36][C:35]=2[CH:34]=[CH:33][CH:32]=1)=[O:30])[C:6]([N:8]([CH3:24])[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:7]>FC(F)(F)C(O)=O>[NH2:41][CH2:40][C:37]1[NH:36][C:35]2[CH:34]=[CH:33][CH:32]=[C:31]([C:29]([NH:28][C:27]3[CH:26]=[CH:25][C:5]([C:6]([N:8]([CH3:24])[C:9]4[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=4[O:16][CH2:17][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[O:7])=[CH:4][C:3]=3[O:2][CH3:1])=[O:30])[C:39]=2[N:38]=1

Participants

3

Reactant 1

HCID 18355035HCID 18355035, compound

Product 1

HCID 18354952HCID 18354952, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-methoxy-N-methyl-N-(4-methyl-2-benzyloxyphenyl)-4-[2-(tert-butoxycarbonyl)aminomethyl-1H-benzimidazol-4-yl]carbonylaminobenzamide (260 mg) in 90% trifluoroacetic acid (2 ml) was stirred at ambient temperature for 2 hours and the solvent was evaporated in vacuo. The residue was stirred with chloroform (10 ml) and saturated aqueous sodium hydrogencarbonate (10 ml) and the organic phase was separated. The solution was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by NH type silica gel column (chloroform) to give 4-(2-aminomethyl-1H-benzimidazol-4-yl)carbonylamino-3-methoxy-N-methyl-N-(4-methyl-2-benzyloxyphenyl)benzamide (130 mg).

Workup

  1. customthe solvent was evaporated in vacuo
  2. customthe organic phase was separated
  3. washThe solution was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by NH type silica gel column (chloroform)

Sources & evidence

ORD record
ord-724b92b4f96942ca9bde7c166e787a52
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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