4-Chloro-6-cyanopicolinic acid → (S)-4-Chloro-6-cyano-N-(3-fluoro-4-(morpholin-2-yl)phenyl)picolinamide hydrochloride

HRID 571887Notes

Reaction equation

HRID 571887 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[N:5]=[C:4]([C:10]([OH:12])=O)[CH:3]=1.C(OC([N:20]1[CH2:25][CH2:24][O:23][C@@H:22]([C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][C:27]=2[F:33])[CH2:21]1)=O)(C)(C)C>>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[N:5]=[C:4]([C:10]([NH:32][C:29]2[CH:30]=[CH:31][C:26]([C@@H:22]3[O:23][CH2:24][CH2:25][NH:20][CH2:21]3)=[C:27]([F:33])[CH:28]=2)=[O:12])[CH:3]=1

Participants

3

Reactant 2

HCID 722120334-Chloro-6-cyanopicolinic acidHCID 86674698(-)-(S)-2-(4-Amino-2-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 71087118(S)-4-Chloro-6-cyano-N-(3-fluoro-4-(morpholin-2-yl)phenyl)picolinamide hydrochloride

Procedure

In analogy to example 83, step a) using 4-chloro-6-cyano-2-pyridine carboxylic acid (CAS 1060812-13-6) instead of 2-(trifluoromethyl)-4-pyridinecarboxylic acid (CAS 131747-41-6) and (−)-(S)-2-(4-Amino-2-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (described in example 83) instead of (+)-(R)-2-(4-Amino-2-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester.

Sources & evidence

ORD record
ord-b44e1cbf3edd4dd3a2b99ced2f378502
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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