Hydrochloric Acid → HCID 136333942, compound

HRID 1426461Notes

Reaction equation

[Br:1][C:2]1[S:6][C:5]([C:7](=[O:9])[NH2:8])=[C:4]([NH:10][C:11]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=O)[CH:3]=1.[OH-].[Na+].Cl>COCCOC>[Br:1][C:2]1[S:6][C:5]2[C:7](=[O:9])[NH:8][C:11]([C:13]3[S:14][CH:15]=[CH:16][N:17]=3)=[N:10][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 3-amino-5-bromothiophene-2-carboxamide (200 mg) produced in Example 1, step D, triethylamine (0.19 mL) and tetrahydrofuran (4.0 μL) was added 1,3-thiazole-2-carbonyl chloride (0.22 g) at 0° C., and the mixture was stirred at room temperature for 2 hr. Water was poured into the reaction system, and the precipitate was collected by filtration to give N-(5-bromo-2-carbamoylthiophen-3-yl)-1,3-thiazole-2-carboxamide (290 mg) as a pale-yellow solid. To N-(5-bromo-2-carbamoylthiophen-3-yl)-1,3-thiazole-2-carboxamide produced above were added 2M aqueous sodium hydroxide solution (1.75 mL) and 1,2-dimethoxyethane (4.0 mL), and the mixture was stirred at 100° C. for 18 hr. The reaction system was neutralized with 1M hydrochloric acid at 0° C. The precipitate was collected by filtration to give the title compound (236 mg) as a white solid.

Workup

filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record: ord-e2d56285eaf54077aecefceffedf19fc
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933069B2

Reaction notes

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