1,4-Dioxane hydrochloride → 5-Chloro-pyridine-2-carboxylic acid[3-((R)-5-amino-3-fluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide hydrochloride

HRID 2196307Notes

Reaction equation

HRID 2196307 reaction equation
C(OC(=O)[NH:7][C:8]1[CH2:9][O:10][CH2:11][C@:12]([C:16]2[CH:21]=[C:20]([NH:22][C:23]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=3)=[O:24])[CH:19]=[CH:18][C:17]=2[F:32])([CH2:14][F:15])[N:13]=1)(C)(C)C.Cl.O1CCOCC1.Cl.CO>C(Cl)Cl>[ClH:31].[NH2:7][C:8]1[CH2:9][O:10][CH2:11][C@:12]([C:16]2[CH:21]=[C:20]([NH:22][C:23]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][N:26]=3)=[O:24])[CH:19]=[CH:18][C:17]=2[F:32])([CH2:14][F:15])[N:13]=1

Participants

5

Reactant 3

HCID 204431481,4-Dioxane hydrochlorideHCID 21893726Hydrochloride methanolHCID 66665679((R)-5-{5-[(5-Chloro-pyridine-2-carbonyl)-amino]-2-fluoro-phenyl}-5-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl)-carbamic acid tert-butyl ester

Product 1

HCID 666658865-Chloro-pyridine-2-carboxylic acid[3-((R)-5-amino-3-fluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-4-fluoro-phenyl]-amide hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ((R)-5-{5-[(5-chloro-pyridine-2-carbonyl)-amino]-2-fluoro-phenyl}-5-fluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl)-carbamic acid tert-butyl ester (106 mg, 0.22 mmol), 4 N HCl/Dioxan (1.1 ml, 4.41 mmol) and 3 N HCl/MeOH in CH2Cl2 was stirred for 15 h at room temperature and for 2 h at 40° C. to complete the conversion. The yellow solution was evaporated and taken up in MeOH. TBME was added and the white precipitate was filtered off to provide the title compound.

Workup

  1. customThe yellow solution was evaporated
  2. additionTBME was added
  3. filtrationthe white precipitate was filtered off

Sources & evidence

ORD record
ord-827f7532aa1c40b7bb5e40428acbc102
Source dataset
uspto-grants-2012_12
Patent number
US08338413B1

Reaction notes

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