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

HRID 571880Notes

Reaction equation

HRID 571880 reaction equation
[ClH:1].[C:2]([C:4]1[CH:5]=[C:6]([CH:23]=[C:24]([O:26][CH3:27])[N:25]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]2[O:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[C:12](F)[CH:11]=1)=[O:8])#[N:3].C(OC(N1CCO[C@@H](C2C=CC(N)=C([Cl:48])C=2)C1)=O)(C)(C)C>>[ClH:48].[Cl:1][C:11]1[CH:12]=[C:13]([C@@H:16]2[O:21][CH2:20][CH2:19][NH:18][CH2:17]2)[CH:14]=[CH:15][C:10]=1[NH:9][C:7](=[O:8])[C:6]1[CH:23]=[C:24]([O:26][CH3:27])[N:25]=[C:4]([C:2]#[N:3])[CH:5]=1

Participants

3

Reactant 2

HCID 68325446(S)-tert-butyl 2-(4-amino-3-chlorophenyl)morpholine-4-carboxylateHCID 71087141(S)-2-Cyano-N-(3-fluoro-4-(morpholin-2-yl)phenyl)-6-methoxyisonicotinamide hydrochloride

Product 1

HCID 71086890(S)-N-(2-Chloro-4-(morpholin-2-yl)phenyl)-2-cyano-6-methoxyisonicotinamide hydrochloride

Procedure

In analogy to example 83, step a) using 2-Cyano-6-methoxy-isonicotinic acid (described in example 107) 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-2b78a057bacd47298a07ee157f07086a
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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