6-Ethoxypyridine-3-carboxylic acid → (S)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-6-ethoxynicotinamide hydrochloride

HRID 571855Notes

Reaction equation

HRID 571855 reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[CH:8][C:7]([C:10]([OH:12])=O)=[CH:6][CH:5]=1)[CH3:2].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:10](=[O:12])[C:7]2[CH:6]=[CH:5][C:4]([O:3][CH2:1][CH3:2])=[N:9][CH:8]=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 64858176-Ethoxypyridine-3-carboxylic acidHCID 71087265(R)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-2-ethoxyisonicotinamide hydrochloride

Product 1

HCID 71087322(S)-N-(3-Chloro-4-(morpholin-2-yl)phenyl)-6-ethoxynicotinamide hydrochloride

Procedure

In analogy to Example 83, step a) using 6-ethoxy-3-pyridinecarboxylic acid (CAS 97455-65-7) 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. White solid. MS (ISP): 362.0 ([M+H]+)

Sources & evidence

ORD record
ord-afd7356c616942c98b2078891b0db8f2
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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