5-Chloro-2-picolinic acid → HCID 89419854, compound

HRID 920195Notes

Reaction equation

HRID 920195 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:31])=[C:16]([C@@:18]2([CH3:30])[N:26]=[C:25]([NH2:27])[C:21]3([CH2:24][CH2:23][CH2:22]3)[S:20](=[O:29])(=[O:28])[CH2:19]2)[CH:17]=1>>[NH2:27][C:25]1[C:21]2([CH2:24][CH2:23][CH2:22]2)[S:20](=[O:28])(=[O:29])[CH2:19][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:31])([CH3:30])[N:26]=1

Participants

3

Reactant 2

HCID 27628725-Chloro-2-picolinic acidHCID 89419882HCID 89419882, compound

Product 1

HCID 89419854HCID 89419854, compoundYield 50,324.699%

Procedure

Prepared from 5-chloropicolinic acid (48.6 mg, 308 μmol, Eq: 1.2) and (R)-7-(5-amino-2-fluoro-phenyl)-7-methyl-5,5-dioxo-5λ6-thia-8-aza-spiro[3.5]non-8-en-9-ylamine (80 mg, 257 mmol, Eq: 1.00) as described for example 2 (method b) to give the title compound (70 mg, 155 mmol, 60.4% yield) as a light yellow foam. MS (ISP): m/z=451.4 [(M+H)+] and 453.2 [(M+2+H)+].

Sources & evidence

ORD record
ord-83365b870b8b4bde8e7cf26b638d948c
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

Loading…