(R)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-2-ethoxyisonicotinamide hydrochloride → (S)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-2-cyano-6-methylisonicotinamide hydrochloride

HRID 571871Notes

Reaction equation

HRID 571871 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:6]([OH:8])=O)#[N:2].Cl.[Cl:14][C:15]1[CH:16]=[C:17]([NH:27]C(=O)C2C=CN=C(OCC)C=2)[CH:18]=[CH:19][C:20]=1[C@H:21]1[O:26][CH2:25][CH2:24][NH:23][CH2:22]1>>[ClH:14].[Cl:14][C:15]1[CH:16]=[C:17]([NH:27][C:6](=[O:8])[C:5]2[CH:9]=[C:10]([CH3:12])[N:11]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH:18]=[CH:19][C:20]=1[C@@H:21]1[O:26][CH2:25][CH2:24][NH:23][CH2:22]1

Participants

3

Reactant 2

HCID 71087265(R)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-2-ethoxyisonicotinamide hydrochlorideHCID 722157192-Cyano-6-methylisonicotinic acid

Product 1

HCID 71086739(S)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-2-cyano-6-methylisonicotinamide hydrochloride

Procedure

In analogy to example 83, step a) using 2-Cyano-6-methyl-isonicotinic acid instead of 2-(trifluoromethyl)-4-pyridinecarboxylic acid (CAS 131747-41-6) and (−)-(S)-2-(4-Amino-2-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (preparation described in example 91) instead of (+)-(R)-2-(4-Amino-2-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester.

Sources & evidence

ORD record
ord-ea57fec50252413b9111e35c187268e2
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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