5-Cyanopyrazine-2-carboxylic acid → 5-Cyano-pyrazine-2-carboxylic acid [3-((4S,4aR,7aR)-2-amino-5,5-difluoro-4-methyl-4,4a,5,6,7,7a-hexahydro-cyclopenta[e][1,3]oxazin-4-yl)-4-fluoro-phenyl]-amide

HRID 710198Notes

Reaction equation

HRID 710198 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C@:8]2([CH3:20])[C@H:13]3[C:14]([F:18])([F:17])[CH2:15][CH2:16][C@H:12]3[O:11][C:10]([NH2:19])=[N:9]2)[CH:7]=1.[C:22]([C:24]1[N:25]=[CH:26][C:27]([C:30](O)=[O:31])=[N:28][CH:29]=1)#[N:23]>>[NH2:19][C:10]1[O:11][C@@H:12]2[CH2:16][CH2:15][C:14]([F:17])([F:18])[C@@H:13]2[C@:8]([C:6]2[CH:7]=[C:2]([NH:1][C:30]([C:27]3[CH:26]=[N:25][C:24]([C:22]#[N:23])=[CH:29][N:28]=3)=[O:31])[CH:3]=[CH:4][C:5]=2[F:21])([CH3:20])[N:9]=1

Participants

3

Reactant 2

HCID 704958325-Cyanopyrazine-2-carboxylic acidHCID 90021263(4S,4aR,7aR)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4-methyl-4,4a,5,6,7,7a-hexahydro-cyclopenta[e][1,3]oxazin-2-ylamine

Product 1

HCID 729437005-Cyano-pyrazine-2-carboxylic acid [3-((4S,4aR,7aR)-2-amino-5,5-difluoro-4-methyl-4,4a,5,6,7,7a-hexahydro-cyclopenta[e][1,3]oxazin-4-yl)-4-fluoro-phenyl]-amideYield 28%

Procedure

The coupling of (4S,4aR,7aR)-4-(5-amino-2-fluoro-phenyl)-5,5-difluoro-4-methyl-4,4a,5,6,7,7a-hexahydro-cyclopenta[e][1,3]oxazin-2-ylamine (intermediate XIIIa-1) and 5-cyano-pyrazine-2-carboxylic acid (CAS 1211533-09-3) following procedure Q yielded the title compound as a light yellow solid (28% yield). MS: m/z=431.3 [M+H]+.

Sources & evidence

ORD record
ord-1cf6d08c782e45f1a7d7fa4b8ce96fbf
Source dataset
uspto-grants-2015_11
Patent number
US09181232B2

Reaction notes

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