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

HRID 571875Notes

Reaction equation

HRID 571875 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:15][C:16](=[O:26])[C:17]2[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]([C:24]#[N:25])[CH:18]=2)[CH:6]=[CH:7][C:8]=1[C@@H:9]1[O:14][CH2:13][CH2:12][NH:11][CH2:10]1.C(OC(N1CCO[C@@H](C2C=CC(N)=CC=2[F:47])C1)=O)(C)(C)C>>[ClH:2].[C:24]([C:19]1[CH:18]=[C:17]([CH:22]=[C:21]([CH3:23])[N:20]=1)[C:16]([NH:15][C:5]1[CH:6]=[CH:7][C:8]([C@@H:9]2[O:14][CH2:13][CH2:12][NH:11][CH2:10]2)=[C:3]([F:47])[CH:4]=1)=[O:26])#[N:25]

Participants

3

Reactant 2

HCID 71086739(S)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-2-cyano-6-methylisonicotinamide hydrochlorideHCID 86674698(-)-(S)-2-(4-Amino-2-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 71086753(S)-2-Cyano-N-(3-fluoro-4-(morpholin-2-yl)phenyl)-6-methylisonicotinamide hydrochloride

Procedure

In analogy to example 83, step a) using 2-Cyano-6-methyl-isonicotinic acid (described in example 112) 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-0977c35d38aa413a828b4fff7a691671
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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