5-Cyanopyridine-2-carboxylic acid → HCID 66562670, compound

HRID 920191Notes

Reaction equation

HRID 920191 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]([OH:11])=O)=[N:7][CH:8]=1)#[N:2].[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([F:31])=[C:17]([C@:19]2([CH3:30])[CH2:24][S:23](=[O:26])(=[O:25])[C:22]([CH3:28])([CH3:27])[C:21]([NH2:29])=[N:20]2)[CH:18]=1>>[NH2:29][C:21]1[C:22]([CH3:27])([CH3:28])[S:23](=[O:25])(=[O:26])[CH2:24][C@:19]([C:17]2[CH:18]=[C:13]([NH:12][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=3)=[O:11])[CH:14]=[CH:15][C:16]=2[F:31])([CH3:30])[N:20]=1

Participants

3

Reactant 2

HCID 124007345-Cyanopyridine-2-carboxylic acidHCID 86715778HCID 86715778, compound

Product 1

HCID 66562670HCID 66562670, compoundYield 67.1%

Procedure

Prepared from 5-cyanopicolinic acid (57.1 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 (101 mg, 235 μmol, 67.1% yield) as a white foam. MS (ISP): m/z=430.3 [(M+H)+].

Sources & evidence

ORD record
ord-9f26f946a1794902a9325ac6638c1933
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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