5-Cyanopyridine-2-carboxylic acid → HCID 90067089, compound

HRID 920194Notes

Reaction equation

HRID 920194 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:33])=[C:17]([C@@:19]2([CH3:32])[N:28]=[C:27]([NH2:29])[C:22]3([CH2:26][CH2:25][CH2:24][CH2:23]3)[S:21](=[O:31])(=[O:30])[CH2:20]2)[CH:18]=1>>[NH2:29][C:27]1[C:22]2([CH2:26][CH2:25][CH2:24][CH2:23]2)[S:21](=[O:30])(=[O:31])[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:33])([CH3:32])[N:28]=1

Participants

3

Reactant 2

HCID 124007345-Cyanopyridine-2-carboxylic acidHCID 89419817HCID 89419817, compound

Product 1

HCID 90067089HCID 90067089, compoundYield 45.7%

Procedure

Prepared from 5-cyanopicolinic acid (27.3 mg, 184 μmol, Eq: 1.2) and (R)-8-(5-amino-2-fluoro-phenyl)-8-methyl-6,6-dioxo-6λ6-thia-9-aza-spiro[4.5]dec-9-en-10-ylamine (50 mg, 154 μmol, Eq: 1.00) as described for example 2 (method b) to give the title compound (32 mg, 70.3 μmol, 45.7% yield) as a white foam. MS (ISP): m/z=456.5 [(M+H)+].

Sources & evidence

ORD record
ord-316a3700c79744e5b698f2b5464d33bb
Source dataset
uspto-grants-2016_03
Patent number
US09273042B2

Reaction notes

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