3-phenylpyridine-2-carboxylic Acid → 3-Phenyl-pyridine-2-carboxylic acid [3-((S)-2-amino-4-methyl-5,6-dihydro-4H-[1,3]oxazin-4-yl)-4-fluoro-phenyl]-amide

HRID 2424353Notes

Reaction equation

HRID 2424353 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.[C:24]1([C:30]2[C:31]([C:36](O)=[O:37])=[N:32][CH:33]=[CH:34][CH:35]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[NH2:7][C:8]1[O:9][CH2:10][CH2:11][C@:12]([C:15]2[CH:20]=[C:19]([NH:21][C:36]([C:31]3[C:30]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:35][CH:34]=[CH:33][N:32]=3)=[O:37])[CH:18]=[CH:17][C:16]=2[F:22])([CH3:14])[N:13]=1

Participants

3

Reactant 2

HCID 27627893-phenylpyridine-2-carboxylic 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 532413473-Phenyl-pyridine-2-carboxylic acid [3-((S)-2-amino-4-methyl-5,6-dihydro-4H-[1,3]oxazin-4-yl)-4-fluoro-phenyl]-amide

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-phenyl-pyridine-2-carboxylic acid followed by deprotection using procedure H yielded the title compound.

Sources & evidence

ORD record
ord-fcb195fee3a343a98d032d4d214abc73
Source dataset
uspto-grants-2011_06
Patent number
US07964594B1

Reaction notes

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