(5-{5-[(5-chloro-pyridine-2-carbonyl)-amino]-2-fluoro-phenyl}-5-trifluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl)-carbamic acid tert-butyl ester → 5-Chloro-pyridine-2-carboxylic acid [3-(5-amino-3-trifluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide

HRID 81554Notes

Reaction equation

HRID 81554 reaction equation
C(OC(=O)[NH:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:18]2[CH:23]=[C:22]([NH:24][C:25]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][N:28]=3)=[O:26])[CH:21]=[CH:20][C:19]=2[F:34])([C:14]([F:17])([F:16])[F:15])[N:13]=1)(C)(C)C>Cl.O1CCOCC1>[NH2:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:18]2[CH:23]=[C:22]([NH:24][C:25]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][N:28]=3)=[O:26])[CH:21]=[CH:20][C:19]=2[F:34])([C:14]([F:17])([F:16])[F:15])[N:13]=1

Participants

4

Reactant 1

HCID 66665516(5-{5-[(5-chloro-pyridine-2-carbonyl)-amino]-2-fluoro-phenyl}-5-trifluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl)-carbamic acid tert-butyl ester

Product 1

HCID 509146895-Chloro-pyridine-2-carboxylic acid [3-(5-amino-3-trifluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 68 mg (0.136 mmol) (5-{5-[(5-chloro-pyridine-2-carbonyl)-amino]-2-fluoro-phenyl}-5-trifluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl)-carbamic acid tert-butyl ester in 2 ml 4N HCl in dioxane was stirred at 40° C. overnight. The mixture was concentrated and crystallized from EtOAc/hexane to yield the title compound as colorless crystals.

Workup

  1. concentrationThe mixture was concentrated
  2. customcrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-74399bbfe17c466c8b8a70884254ca4a
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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