5-(Difluoromethoxy)picolinic acid → 5-Difluoromethoxy-pyridine-2-carboxylic acid [3-((R)-5-amino-3-methyl-1,1-dioxo-1,2,3,6-tetrahydro-1lambda6-[1,4]thiazin-3-yl)-4-fluoro-phenyl]-amide

HRID 920189Notes

Reaction equation

HRID 920189 reaction equation
[F:1][CH:2]([F:13])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=1.[NH2:14][C:15]1[CH:16]=[CH:17][C:18]([F:31])=[C:19]([C@:21]2([CH3:30])[CH2:26][S:25](=[O:28])(=[O:27])[CH2:24][C:23]([NH2:29])=[N:22]2)[CH:20]=1>>[NH2:29][C:23]1[CH2:24][S:25](=[O:27])(=[O:28])[CH2:26][C@:21]([C:19]2[CH:20]=[C:15]([NH:14][C:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][CH:2]([F:1])[F:13])=[CH:9][N:8]=3)=[O:12])[CH:16]=[CH:17][C:18]=2[F:31])([CH3:30])[N:22]=1

Participants

3

Reactant 2

HCID 574758715-(Difluoromethoxy)picolinic acidHCID 90067101(R)-5-(5-amino-2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1lambda6-[1,4]thiazin-3-ylamine

Product 1

HCID 725479625-Difluoromethoxy-pyridine-2-carboxylic acid [3-((R)-5-amino-3-methyl-1,1-dioxo-1,2,3,6-tetrahydro-1lambda6-[1,4]thiazin-3-yl)-4-fluoro-phenyl]-amideYield 52.1%

Procedure

Prepared from 5-(difluoromethoxy)picolinic acid (69.7 mg, 369 μmol, Eq: 1.00) and (R)-5-(5-amino-2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1λ6-[1,4]thiazin-3-ylamine (100 mg, 369 μmol, Eq: 1.00) as described for example 2 (method b) to give the title compound (85 mg, 192 μmol, 52.1% yield) as a white foam. MS (ISP): m/z=443.4 [(M+H)].

Sources & evidence

ORD record
ord-2153c01f58e246c4a7b4d292984b9700
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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