HCID 68773176, compound → HCID 57785863, compound

HRID 1399123Notes

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:15]([CH2:16][CH2:17][CH2:18]O)[C:14]3[C:20]([C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:22]=[C:23]([Cl:24])[C:13]=3[N:12]=2)=[C:6]([CH3:29])[CH:5]=1)(=[O:3])[NH2:2]>C1C(Cl)=CC=C(Cl)C=1>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:11]3=[N:12][C:13]4[C:14](=[C:20]([C:25]([O:27][CH3:28])=[O:26])[CH:21]=[CH:22][C:23]=4[Cl:24])[N:15]3[CH2:16][CH2:17][CH2:18]2)=[C:6]([CH3:29])[CH:5]=1)(=[O:3])[NH2:2]

Participants

Conditions

Temperature: 110 °C

Procedure

Tsunoda reagent (904 mg, 3.74 mmol) was added to a stirred suspension of methyl 2-[(4-carbamoyl-2-methylphenyl)amino]-4-chloro-1-(3-hydroxypropyl)-1H-benzimidazole-7-carboxylate (1.30 g, 3.12 mmol) in dichlorobenzene (30 mL) at room temperature, and the mixture was stirred at 110° C. for 23 hr. The mixture was concentrated in vacuo, crystallized from ethyl acetate/diisopropyl ether and washed with diisopropyl ether to give the title compound as a pale yellow powder (761 mg, 1.91 mmol, 61%).

Workup

concentrationThe mixture was concentrated in vacuo
customcrystallized from ethyl acetate/diisopropyl ether
washwashed with diisopropyl ether

Sources & evidence

ORD record: ord-ae0f4238f35e47af90d908e76bf5a63a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901141B2

Reaction notes

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