5-Chloro-2-picolinic acid → 5-Chloro-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 920188Notes

Reaction equation

HRID 920188 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([F:28])=[C:16]([C@:18]2([CH3:27])[CH2:23][S:22](=[O:25])(=[O:24])[CH2:21][C:20]([NH2:26])=[N:19]2)[CH:17]=1>>[NH2:26][C:20]1[CH2:21][S:22](=[O:24])(=[O:25])[CH2:23][C@:18]([C:16]2[CH:17]=[C:12]([NH:11][C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=3)=[O:10])[CH:13]=[CH:14][C:15]=2[F:28])([CH3:27])[N:19]=1

Participants

3

Reactant 2

HCID 27628725-Chloro-2-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 725481995-Chloro-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 46%

Procedure

Prepared from 5-chloropicolinic acid (73.5 mg, 466 μmol, Eq: 1.1) and (R)-5-(5-amino-2-fluoro-phenyl)-5-methyl-1,1-dioxo-1,2,5,6-tetrahydro-1λ6-[1,4]thiazin-3-ylamine (115 mg, 424 μmol, Eq: 1.00) as described for example 2 (method b) to give the title compound (80 mg, 195 μmol, 45.9% yield) as a light yellow solid. MS (ISP): m/z=411.4 [(M+H)+] and 413.2 [(M+2+H)+].

Sources & evidence

ORD record
ord-cd98dfb86c2e4cf9b95b8f6f5feffd4c
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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