(S)-tert-Butyl 2-(4-amino-3-fluorophenyl)morpholine-4-carboxylate → (S)-2-Cyano-N-(2-fluoro-4-(morpholin-2-yl)phenyl)-6-methoxyisonicotinamide hydrochloride

HRID 571878Notes

Reaction equation

HRID 571878 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([F:48])C=2)C1)=O)(C)(C)C>>[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)=[CH:12][C:11]=1[F:48])=[O:8])#[N:3]

Participants

3

Reactant 2

HCID 68325451(S)-tert-Butyl 2-(4-amino-3-fluorophenyl)morpholine-4-carboxylateHCID 71087141(S)-2-Cyano-N-(3-fluoro-4-(morpholin-2-yl)phenyl)-6-methoxyisonicotinamide hydrochloride

Product 1

HCID 71086689(S)-2-Cyano-N-(2-fluoro-4-(morpholin-2-yl)phenyl)-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-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (described in example 1 h) instead of (+)-(R)-2-(4-Amino-2-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester.

Sources & evidence

ORD record
ord-de4d2173711b4e0f9a06df372c420af3
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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