Hydrochloric Acid → 5-Amino-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid

HRID 521833Notes

Reaction equation

HRID 521833 reaction equation
C(OC([NH:8][C:9]1[S:13][C:12]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])=[N:11][C:10]=1[C:22]([OH:24])=[O:23])=O)(C)(C)C.Cl.O1CCOCC1>CO>[NH2:8][C:9]1[S:13][C:12]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])=[N:11][C:10]=1[C:22]([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 674381985-((Tert-butoxycarbonyl)amino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid

Product 1

HCID 594556885-Amino-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid (530 mg, 1.49 mmol) in MeOH (10 mL) was added HCl in dioxane (4 M, 5 mL, 20.0 mmol). The reaction mixture was stirred at room temperature for 48 hr and the solvents removed under reduced pressure to give 5-amino-2-(2,6-difluorophenyl)thiazole-4-carboxylic acid as the hydrochloride salt. 1H NMR (400 MHz, d6-DMSO) δ 7.57-7.45 (m, 1H), 7.29-7.18 (m, 2H), 5.30 (br s, 3H).

Workup

  1. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-30e174f4ff8e4951a68ea50a657b75d3
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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