5-(But-2-ynyloxy)pyrazine-2-carboxylic acid → HCID 71652164, compound

HRID 2178157Notes

Reaction equation

HRID 2178157 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C@:8]2([CH3:19])[CH2:13][C@@H:12]([C:14]([F:17])([F:16])[F:15])[O:11][C:10]([NH2:18])=[N:9]2)[CH:7]=1.[CH2:21]([O:25][C:26]1[N:27]=[CH:28][C:29]([C:32](O)=[O:33])=[N:30][CH:31]=1)[C:22]#[C:23][CH3:24]>>[NH2:18][C:10]1[O:11][C@H:12]([C:14]([F:16])([F:17])[F:15])[CH2:13][C@:8]([C:6]2[CH:7]=[C:2]([NH:1][C:32]([C:29]3[CH:28]=[N:27][C:26]([O:25][CH2:21][C:22]#[C:23][CH3:24])=[CH:31][N:30]=3)=[O:33])[CH:3]=[CH:4][C:5]=2[F:20])([CH3:19])[N:9]=1

Participants

3

Reactant 2

HCID 584486775-(But-2-ynyloxy)pyrazine-2-carboxylic acidHCID 71663148(4S,6S)-4-(5-amino-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

Product 1

HCID 71652164HCID 71652164, compound

Procedure

The coupling of (4S,6S)-4-(5-amino-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine (XI-1) and 5-(but-2-ynyloxy)pyrazine-2-carboxylic acid [G. Csjernyik et al. WO2012087237 (2012)] following General Procedure F yielded the title compound as a white solid. MS: m/z=466.5 [M+H]+.

Sources & evidence

ORD record
ord-7be9223d631b4963b3d25a1dff4222d8
Source dataset
uspto-grants-2015_06
Patent number
US09067926B2

Reaction notes

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