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

HRID 571851Notes

Reaction equation

HRID 571851 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[CH:6][N:5]=1)[CH3:2].C(OC([N:20]1[CH2:25][CH2:24][O:23][C@H:22]([C:26]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][C:27]=2[Cl:33])[CH2:21]1)=O)(C)(C)C>>[ClH:33].[Cl:33][C:27]1[CH:28]=[C:29]([NH:32][C:10](=[O:12])[C:8]2[CH:7]=[CH:6][N:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:9]=2)[CH:30]=[CH:31][C:26]=1[C@H:22]1[O:23][CH2:24][CH2:25][NH:20][CH2:21]1

Participants

3

Reactant 2

HCID 5924012-Ethoxyisonicotinic acidHCID 86674693(+)-(R)-2-(4-Amino-2-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 71087265(R)-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 (+)-(R)-2-(4-Amino-2-chloro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester 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-bbddc9adb9a14b259668e0e3e8c0cc88
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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