Trimethyl orthoacetate → 5-(Benzoxazol-2-yl)-2-methyl-1-(2-phenylethyl)benzimidazole

HRID 74225Notes

Reaction equation

HRID 74225 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]3[O:18][C:19]4[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=4[N:21]=3)=[CH:13][C:11]=2[NH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO[C:28](OC)(OC)[CH3:29]>CO>[O:18]1[C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=[C:17]1[C:14]1[CH:15]=[CH:16][C:10]2[N:9]([CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:28]([CH3:29])=[N:12][C:11]=2[CH:13]=1

Participants

4

Reactant 2

HCID 15050Trimethyl orthoacetateHCID 674988582-(2-(2-Phenylethyl)aminoanilin-5-yl)benzoxazole

Product 1

HCID 674982835-(Benzoxazol-2-yl)-2-methyl-1-(2-phenylethyl)benzimidazoleYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol (5 mL) solution of 2-(2-(2-phenylethyl)aminoanilin-5-yl)benzoxazole (see Working Example 52-1) (140 mg, 0.425 mmol) was added 1,1,1-trimethoxyethane (61.3 mg, 0.510 mmol), and this was stirred at room temperature for 6 hours. After the reaction was complete, this was concentrated, and the residue obtained was purified by silica gel column chromatography to yield the title compound (98.4 mg, 66% yield) as white crystals.

Workup

  1. concentrationthis was concentrated
  2. customthe residue obtained
  3. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d790932fc97440b28878bf8ff9eb03ef
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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