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 221753Notes

Reaction equation

HRID 221753 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-942fd7121c714d01aa9060a979e91ef3
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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