2-Ethoxyisonicotinic acid → (S)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-2-ethoxyisonicotinamide hydrochloride

HRID 571854Notes

Reaction equation

HRID 571854 reaction equation
C(OC1C=C(C(O)=O)C=CN=1)C.Cl.[Cl:14][C:15]1[CH:16]=[C:17]([NH:27][C:28](=[O:38])[C:29]2[CH:34]=[CH:33][N:32]=[C:31]([O:35][CH2:36][CH3:37])[CH:30]=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:28](=[O:38])[C:29]2[CH:34]=[CH:33][N:32]=[C:31]([O:35][CH2:36][CH3:37])[CH:30]=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 5924012-Ethoxyisonicotinic acidHCID 71087265(R)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-2-ethoxyisonicotinamide hydrochloride

Product 1

HCID 71087355(S)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-2-ethoxyisonicotinamide hydrochloride

Procedure

In analogy to Example 83, step a) using 2-ethoxy-4-pyridinecarboxylic acid (CAS 91940-86-2) 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. Light yellow foam. MS (ISP): 362.0 ([M+H]+)

Sources & evidence

ORD record
ord-eefc002f3ae74fe1903c98028544fd9b
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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