Methyl 2,2,2-trichloroacetimidate → HCID 178494095, compound

HRID 470332Notes

Reaction equation

HRID 470332 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([O:14][CH3:15])=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[NH2:16].[Cl:17][C:18]([Cl:24])([Cl:23])[C:19](=N)OC>C(O)(=O)C>[CH3:15][O:14][C:9]1[C:8]([C:6]2[CH:5]=[CH:4][C:3]3[NH:16][C:19]([C:18]([Cl:24])([Cl:23])[Cl:17])=[N:1][C:2]=3[CH:7]=2)=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 100479Methyl 2,2,2-trichloroacetimidateHCID 59784760HCID 59784760, compound

Product 1

HCID 178494095HCID 178494095, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-amino-4-(2-methoxypyridin-3-yl)phenylamine 3 obtained from above reaction (0.215 g, 1 mmol) in acetic acid (2 mL) cooled to 0° C. was added methyl trichloroacetimidate (0.193 g, 1.1 mmol) under N2 atmosphere and resulting reaction mixture was stirred at room temperature for 3 h. Acetic acid was evaporated to give crude 5-(2-methoxypyridin-3-yl)-2-(trichloromethyl)-1H-benzimidazole which was used as such in the following step (0.3 g). Reference: Louvet, P.; Lallement, G.; Pemot-Marino, I.; Luu-Duc, C.; Blanchet, G. Eur. J. Med. Chem. 1993, 28, 71-75.

Workup

  1. customresulting
  2. customreaction mixture
  3. customAcetic acid was evaporated

Sources & evidence

ORD record
ord-60dd7c9d903f413c95d6fc238a2188bf
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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