3,5-Dichloro-2-pyridinecarboxylic acid → N-[3-[(4S)-2-amino-4-methyl-5,6-dihydro-1,3-oxazin-4-yl]-4-fluorophenyl]-3,5-dichloropyridine-2-carboxamide

HRID 2424344Notes

Reaction equation

HRID 2424344 reaction equation
C(OC(=O)[NH:7][C:8]1[O:9][CH2:10][CH2:11][C@:12]([C:15]2[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][C:16]=2[F:22])([CH3:14])[N:13]=1)(C)(C)C.[Cl:24][C:25]1[C:26]([C:32](O)=[O:33])=[N:27][CH:28]=[C:29]([Cl:31])[CH:30]=1>>[NH2:7][C:8]1[O:9][CH2:10][CH2:11][C@:12]([C:15]2[CH:20]=[C:19]([NH:21][C:32]([C:26]3[C:25]([Cl:24])=[CH:30][C:29]([Cl:31])=[CH:28][N:27]=3)=[O:33])[CH:18]=[CH:17][C:16]=2[F:22])([CH3:14])[N:13]=1

Participants

3

Reactant 2

HCID 2199893,5-Dichloro-2-pyridinecarboxylic acidHCID 67234727[(S)-4-(5-amino-2-fluoro-phenyl)-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-yl]-carbamic acid tert-butyl ester

Product 1

HCID 53241150N-[3-[(4S)-2-amino-4-methyl-5,6-dihydro-1,3-oxazin-4-yl]-4-fluorophenyl]-3,5-dichloropyridine-2-carboxamide

Procedure

The coupling of [(S)-4-(5-amino-2-fluoro-phenyl)-4-methyl-5,6-dihydro-4H-[1,3]oxazin-2-yl]-carbamic acid tert-butyl ester from experiment F1 (R3=Me) and 3,5-dichloro-pyridine-2-carboxylic acid followed by deprotection using procedure H yielded the title compound.

Sources & evidence

ORD record
ord-d9916881749b4cf184a7360800236e68
Source dataset
uspto-grants-2011_06
Patent number
US07964594B1

Reaction notes

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