(S)-tert-butyl 2-(4-amino-3-chlorophenyl)morpholine-4-carboxylate → (S)-N-(2-Chloro-4-(morpholin-2-yl)phenyl)-2-cyano-6-methylisonicotinamide hydrochloride

HRID 571879Notes

Reaction equation

HRID 571879 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)=C([Cl:47])C=2)C1)=O)(C)(C)C>>[ClH:2].[Cl:47][C:6]1[CH:7]=[C:8]([C@@H:9]2[O:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:3]=[CH:4][C:5]=1[NH:15][C:16](=[O:26])[C:17]1[CH:22]=[C:21]([CH3:23])[N:20]=[C:19]([C:24]#[N:25])[CH:18]=1

Participants

3

Reactant 2

HCID 68325446(S)-tert-butyl 2-(4-amino-3-chlorophenyl)morpholine-4-carboxylateHCID 71086739(S)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-2-cyano-6-methylisonicotinamide hydrochloride

Product 1

HCID 71086864(S)-N-(2-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 (described in example 112) instead of 2-(trifluoromethyl)-4-pyridinecarboxylic acid (CAS 131747-41-6) and (−)-(S)-2-(4-Amino-3-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (described in example 29a) instead of (+)-(R)-2-(4-Amino-2-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester.

Sources & evidence

ORD record
ord-c0a30b3c022b4beb8b991941f705cafa
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

Loading…