6-Cyanopyridine-2-carboxylic acid → (S)-N-(2-Chloro-4-(morpholin-2-yl)phenyl)-6-cyanopicolinamide hydrochloride

HRID 571857Notes

Reaction equation

HRID 571857 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=1)#[N:2].C(OC([N:19]1[CH2:24][CH2:23][O:22][C@@H:21]([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[C:27]([Cl:32])[CH:26]=2)[CH2:20]1)=O)(C)(C)C>>[ClH:32].[Cl:32][C:27]1[CH:26]=[C:25]([C@@H:21]2[O:22][CH2:23][CH2:24][NH:19][CH2:20]2)[CH:30]=[CH:29][C:28]=1[NH:31][C:9](=[O:11])[C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([C:1]#[N:2])[N:8]=1

Participants

3

Reactant 2

HCID 212530396-Cyanopyridine-2-carboxylic acidHCID 68325446(S)-tert-butyl 2-(4-amino-3-chlorophenyl)morpholine-4-carboxylate

Product 1

HCID 71087101(S)-N-(2-Chloro-4-(morpholin-2-yl)phenyl)-6-cyanopicolinamide hydrochloride

Procedure

In analogy to example 79, step a) using 6-cyano-2-pyridinecarboxylic acid (CAS 872602-74-9) instead of 4-cyanopicolinic acid (CAS 640296-19-1) and (−)-(S)-2-(4-Amino-3-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (example 29a) instead of (−)-(S)-2-(4-Amino-3-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester. White solid. MS (ISP): 341.1 ([M+H]+)

Sources & evidence

ORD record
ord-d84b939729e54f93a05f1b2a8754d64e
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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