Methyl 2,2,2-trichloroacetimidate → Methyl 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-(trichloromethyl)-1H-benzimidazole-6-carboxylate

HRID 1521686Notes

Reaction equation

HRID 1521686 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[NH:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[Cl:24][C:25]([Cl:31])([Cl:30])[C:26](=N)OC>C(O)(=O)C>[C:20]([O:19][C:17]([NH:16][CH2:15][CH2:14][CH2:13][N:12]1[C:3]2[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=2[N:1]=[C:26]1[C:25]([Cl:31])([Cl:30])[Cl:24])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 100479Methyl 2,2,2-trichloroacetimidateHCID 11962077Methyl 4-amino-3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)benzoate

Product 1

HCID 67236445Methyl 1-{3-[(tert-butoxycarbonyl)amino]propyl}-2-(trichloromethyl)-1H-benzimidazole-6-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of methyl 4-amino-3-({3-[(tert-butoxycarbonyl)amino]propyl}amino)benzoate (4.7 g, 14.5 mmol) in acetic acid (50 mL) is added methyl trichloroacetimidate (3.1 g, 17.4 mmol). After 3 h at room temperature, the solvent is evaporated, the residue is dissolved in EtOAc, and is washed with Na2CO3 and brine. The organic layer is dried (Na2SO4) and evaporated. The residue is triturated with hexanes to afford the title compound (5.2 g, 80%) as a fine powder. LCMS (Method T), 1.85 min, 450.63 (MH+).

Workup

  1. customthe solvent is evaporated
  2. dissolutionthe residue is dissolved in EtOAc
  3. washis washed with Na2CO3 and brine
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. customevaporated
  6. customThe residue is triturated with hexanes

Sources & evidence

ORD record
ord-9060c1155b03415da17abcf4f32591ef
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

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