Hydrochloric Acid → 2-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (4-[1,4]diazepan-1-yl-phenyl)-amide hydrochloride

HRID 1509871Notes

Reaction equation

HRID 1509871 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[N:25]=[C:26]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[O:27][C:28]=3[C:29]([F:32])([F:31])[F:30])=[O:23])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.O1CCOCC1.[ClH:45]>CO>[ClH:45].[N:11]1([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[N:25]=[C:26]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[O:27][C:28]=3[C:29]([F:32])([F:30])[F:31])=[O:23])=[CH:17][CH:16]=2)[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59185678HCID 59185678, compound

Product 1

HCID 866388652-Phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (4-[1,4]diazepan-1-yl-phenyl)-amide hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-[1,4]diazepane-1-carboxylic acid tert-butyl ester (1.64 g, 3.1 mmol) in methanol (50 mL) and hydrogen chloride in dioxane (4M, 10 mL, 40 mmol) was stirred at room temperature for 24 hr. The solvents were removed under vacuum to yield 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (4-[1,4]diazepan-1-yl-phenyl)-amide hydrochloride salt (1.57 g, 99% yield) as a white solid. ES-MS for the neutral form C22H21F3N4O2 calcd. (m/e) 430, observed 431 (M+H).

Workup

  1. customThe solvents were removed under vacuum

Sources & evidence

ORD record
ord-223fab80a31c4b2e9985c2c5f6a4ea29
Source dataset
uspto-grants-2012_07
Patent number
US08211884B2

Reaction notes

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