5-Difluoromethympyrazine-2-carboxylic acid → HCID 72548197, compound

HRID 920193Notes

Reaction equation

HRID 920193 reaction equation
[F:1][CH:2]([F:12])[C:3]1[N:4]=[CH:5][C:6]([C:9]([OH:11])=O)=[N:7][CH:8]=1.[NH2:13][C:14]1[CH:15]=[CH:16][C:17]([F:32])=[C:18]([C@:20]2([CH3:31])[CH2:25][S:24](=[O:27])(=[O:26])[C:23]([CH3:29])([CH3:28])[C:22]([NH2:30])=[N:21]2)[CH:19]=1>>[NH2:30][C:22]1[C:23]([CH3:28])([CH3:29])[S:24](=[O:26])(=[O:27])[CH2:25][C@:20]([C:18]2[CH:19]=[C:14]([NH:13][C:9]([C:6]3[CH:5]=[N:4][C:3]([CH:2]([F:1])[F:12])=[CH:8][N:7]=3)=[O:11])[CH:15]=[CH:16][C:17]=2[F:32])([CH3:31])[N:21]=1

Participants

3

Reactant 2

HCID 574685755-Difluoromethympyrazine-2-carboxylic acidHCID 86715778HCID 86715778, compound

Product 1

HCID 72548197HCID 72548197, compoundYield 47.9%

Procedure

Prepared from commercially available 5-(difluoromethyl)pyrazine-2-carboxylic acid (CAS-no. 1174321-06-2) (48.9 mg, 281 μmol, Eq: 1.2) and (R)-5-(5-amino-2-fluoro-phenyl)-2,2,5-trimethyl-1,1-dioxo-1,2,5,6-tetrahydro-1λ6-[1,4]thiazin-3-ylamine (70 mg, 234 μmol, Eq: 1.00) as described for example 2 (method b) to give the title compound (51 mg, 112 μmol, 47.9% yield) as a light yellow foam. MS (ISP): m/z=456.5 [(M+H)+].

Sources & evidence

ORD record
ord-0edab0933c53414688eac2b5cf37040d
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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