5-Chloro-2-picolinic acid → HCID 66562362, compound

HRID 920190Notes

Reaction equation

HRID 920190 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:30])=[C:16]([C@:18]2([CH3:29])[CH2:23][S:22](=[O:25])(=[O:24])[C:21]([CH3:27])([CH3:26])[C:20]([NH2:28])=[N:19]2)[CH:17]=1>>[NH2:28][C:20]1[C:21]([CH3:26])([CH3:27])[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:30])([CH3:29])[N:19]=1

Participants

3

Reactant 2

HCID 27628725-Chloro-2-picolinic acidHCID 86715778HCID 86715778, compound

Product 1

HCID 66562362HCID 66562362, compoundYield 97.4%

Procedure

Prepared from 5-chloropicolinic acid (60.8 mg, 386 μmol, Eq: 1.1) 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 (105 mg, 351 μmol, Eq: 1.00) as described for example 2 (method b) to give the title compound (150 mg, 342 μmol, 97.4% yield) as a white foam. MS (ISP): m/z=439.3 [(M+H)+] and 441.2 [(M+2+H)+].

Sources & evidence

ORD record
ord-66fa17e94a824e4597144d234aab3ab0
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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