Tetrahydrofuran → HCID 71147266, compound

HRID 1409054Notes

Reaction equation

HRID 1409054 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([Br:7])[S:4][C:3]=1[C:8]([NH2:10])=[O:9].C(N(CC)CC)C.O1CCCC1.[S:23]1[CH:27]=[CH:26][N:25]=[C:24]1[C:28](Cl)=[O:29]>O>[Br:7][C:5]1[S:4][C:3]([C:8](=[O:9])[NH2:10])=[C:2]([NH:1][C:28]([C:24]2[S:23][CH:27]=[CH:26][N:25]=2)=[O:29])[CH:6]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 27952111,3-Thiazole-2-carbonyl chlorideHCID 219758623-Amino-5-bromothiophene-2-carboxamide

Product 1

HCID 71147266HCID 71147266, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 mL) 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

  1. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-a720d670375b47128f9fb0a757974fa1
Source dataset
uspto-grants-2014_12
Patent number
US08921354B2

Reaction notes

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