5-Cyanopyridine-2-carboxylic acid → HCID 71532014, compound

HRID 920196Notes

Reaction equation

HRID 920196 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:32])=[C:17]([C@@:19]2([CH3:31])[N:27]=[C:26]([NH2:28])[C:22]3([CH2:25][CH2:24][CH2:23]3)[S:21](=[O:30])(=[O:29])[CH2:20]2)[CH:18]=1>>[NH2:28][C:26]1[C:22]2([CH2:25][CH2:24][CH2:23]2)[S:21](=[O:29])(=[O:30])[CH2:20][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:32])([CH3:31])[N:27]=1

Participants

3

Reactant 2

HCID 124007345-Cyanopyridine-2-carboxylic acidHCID 89419882HCID 89419882, compound

Product 1

HCID 71532014HCID 71532014, compoundYield 39,419.602%

Procedure

Prepared from 5-cyanopicolinic acid (33.1 mg, 224 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 (58 mg, 186 mmol, Eq: 1.00) as described for example 2 (method b) to give the title compound (39 mg, 88.3 mmol, 47.4% yield) as a light yellow foam. MS (ISP): m/z=442.4 [(M+H)+].

Sources & evidence

ORD record
ord-35e24888b3694d34a41f8ecfb9102170
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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