6-Cyanopyridine-3-carboxylic acid → (S)-N-(2-Chloro-4-(morpholin-2-yl)phenyl)-6-cyanonicotinamide hydrochloride

HRID 571860Notes

Reaction equation

HRID 571860 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]([OH:11])=O)=[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:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[N:8][CH:7]=1

Participants

3

Reactant 2

HCID 27611086-Cyanopyridine-3-carboxylic acidHCID 68325446(S)-tert-butyl 2-(4-amino-3-chlorophenyl)morpholine-4-carboxylate

Product 1

HCID 71086975(S)-N-(2-Chloro-4-(morpholin-2-yl)phenyl)-6-cyanonicotinamide hydrochloride

Procedure

In analogy to example 79, step a) using 6-cyano-3-pyridinecarboxylic acid (CAS 70165-31-0) 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-ef0bae9a5b8749fe8f9955aa83998fca
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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