Trifluoroacetic acid → HCID 66785638, compound

HRID 1096636Notes

Reaction equation

HRID 1096636 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[N:18]([CH2:19][CH2:20][CH2:21][O:22][CH3:23])[C:17]3[C:24]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][CH:26]=[CH:27][C:16]=3[N:15]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:23][O:22][CH2:21][CH2:20][CH2:19][N:18]1[C:17]2[C:24]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][CH:26]=[CH:27][C:16]=2[N:15]=[C:14]1[CH:10]1[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66786161HCID 66786161, compound

Product 1

HCID 66785638HCID 66785638, compoundYield 18.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(1-(tert-butoxycarbonyl)piperidin-3-yl)-1-(3-methoxypropyl)-1H-benzo[d]imidazole-7-carboxylate (44B) (1.91 mmol, 400 mg) in DCM (10 mL) was added TFA (2 mL). The reaction solution was stirred at rt for 1 hr and then concentrated in vacuo. The residue was purified by preparative LC/MS (15-40% CH3CN in H2O) to afford methyl 1-(3-methoxypropyl)-2-(piperidin-3-yl)-1H-benzo[d]imidazole-7-carboxylate (44C) (0.36 mmol, 120 mg, yield: 18.8%). EST-MS: m/z 332.4 (M+H)+.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative LC/MS (15-40% CH3CN in H2O)

Sources & evidence

ORD record
ord-609990a34b7244c4800cd7cc237e6225
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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