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

HRID 74229Notes

Reaction equation

HRID 74229 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]2[CH:12]=[CH:11][C:10]([C:13]3[O:14][C:15]4[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=4[N:17]=3)=[CH:9][C:7]=2[NH2:8])[CH2:3][CH2:2]1.CO[C:24](OC)(OC)[CH3:25]>CO>[O:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=[C:13]1[C:10]1[CH:11]=[CH:12][C:6]2[N:5]([CH2:4][CH:1]3[CH2:2][CH2:3]3)[C:24]([CH3:25])=[N:8][C:7]=2[CH:9]=1

Participants

4

Reactant 2

HCID 15050Trimethyl orthoacetateHCID 67498091HCID 67498091, compound

Product 1

HCID 674980925-(Benzoxazol-2-yl)-2-methyl-1-cyclopropylmethylbenzimidazoleYield 63.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol (5 mL) solution of 2-(2-cyclopropylmethylaminoanilin-5-yl)benzoxazole (see Working Example 54-1) (140 mg, 0.425 mmol) was added 1,1,1-trimethoxyethane (75 mg, 0.624 mmol), and this was stirred at room temperature for 10 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 (81.9 mg, 54% yield) as pink crystals.

Workup

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

Sources & evidence

ORD record
ord-34159f691ed3462a99625c552f00d970
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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