5-Cyanopyridine-2-carboxylic acid → HCID 71204773, compound

HRID 1422593Notes

Reaction equation

HRID 1422593 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:24])=[C:6]([C@:8]23[CH2:15][C@H:14]2[CH2:13][CH2:12][S:11][C:10]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:9]3)[CH:7]=1.[C:25]([C:27]1[CH:28]=[CH:29][C:30]([C:33](O)=[O:34])=[N:31][CH:32]=1)#[N:26]>>[C:25]([C:27]1[CH:28]=[CH:29][C:30]([C:33]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([F:24])=[C:6]([C@:8]34[CH2:15][C@H:14]3[CH2:13][CH2:12][S:11][C:10]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[N:9]4)[CH:7]=2)=[O:34])=[N:31][CH:32]=1)#[N:26]

Participants

3

Reactant 2

HCID 124007345-Cyanopyridine-2-carboxylic acidHCID 86675579HCID 86675579, compound

Product 1

HCID 71204773HCID 71204773, compoundYield 46.5%

Procedure

Prepared in an analogous manner as described for intermediate rac-A9a from tert-butyl (1S,7S)-1-(5-amino-2-fluorophenyl)-4-thia-2-azabicyclo[5.1.0]oct-2-en-3-ylcarbamate (intermediate (−)-A8a) (86.7 mg, 247 μmol) and commercially available 5-cyanopicolinic acid to give the tert-butyl (1S,7S)-1-(5-(5-cyanopicolinamido)-2-fluorophenyl)-4-thia-2-azabicyclo[5.1.0]oct-2-en-3-ylcarbamate (65 mg, 135 μmol, 46.5% yield) as a yellow oil. MS (ISP): m/z=482.1 [(M+H)+].

Workup

  1. customPrepared in an analogous manner

Sources & evidence

ORD record
ord-cb29c5649d874490966e8742eaef4469
Source dataset
uspto-grants-2015_01
Patent number
US08927535B2

Reaction notes

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