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

HRID 74227Notes

Reaction equation

HRID 74227 reaction equation
[CH:1]1([NH:4][C:5]2[CH:11]=[CH:10][C:9]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=4[N:16]=3)=[CH:8][C:6]=2[NH2:7])[CH2:3][CH2:2]1.CO[C:23](OC)(OC)[CH3:24]>CO>[O:13]1[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=[C:12]1[C:9]1[CH:10]=[CH:11][C:5]2[N:4]([CH:1]3[CH2:2][CH2:3]3)[C:23]([CH3:24])=[N:7][C:6]=2[CH:8]=1

Participants

4

Reactant 2

HCID 15050Trimethyl orthoacetateHCID 674988612-(2-Cyclopropylaminoanilin-5-yl)benzoxazole

Product 1

HCID 674986355-(Benzoxazol-2-yl)-2-methyl-1-cyclopropylbenzimidazoleYield 51.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol (5 mL) solution of 2-(2-cyclopropylaminoanilin-5-yl)benzoxazole (see Working Example 53-1) (140 mg, 0.425 mmol) was added 1,1,1-trimethoxyethane (75 mg, 0.624 mmol), and this was stirred at room temperature for 6 hours. After the reaction was complete, this was concentrated, and the residue obtained was purified by silica gel column chromatography to yield the imidazole (63.5 mg, 42% yield).

Workup

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

Sources & evidence

ORD record
ord-ef31e465b2324e81baa23f57a715f056
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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