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

HRID 571868Notes

Reaction equation

HRID 571868 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[N:5]=[C:4]([C:10]([OH:12])=O)[CH:3]=1.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])=[C:28]([F:33])[CH:27]=2)[CH2:21]1)=O)(C)(C)C>>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[N:5]=[C:4]([C:10]([NH:32][C:29]2[CH:30]=[CH:31][C:26]([C@@H:22]3[O:23][CH2:24][CH2:25][NH:20][CH2:21]3)=[CH:27][C:28]=2[F:33])=[O:12])[CH:3]=1

Participants

3

Reactant 2

HCID 68325451(S)-tert-Butyl 2-(4-amino-3-fluorophenyl)morpholine-4-carboxylateHCID 722120334-Chloro-6-cyanopicolinic acid

Product 1

HCID 71087318(S)-4-Chloro-6-cyano-N-(2-fluoro-4-(morpholin-2-yl)phenyl)picolinamide hydrochloride

Procedure

In analogy to Example 83, step a) using 4-chloro-6-cyano-2-pyridine carboxylic acid (CAS 1060812-13-6) 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 (example 1 step h) instead of (+)-(R)-2-(4-Amino-2-fluoro-phenyl)-morpholine-4-carboxylic acid tert-butyl ester. White solid. MS (ISP): 359.1 ([M+H]+)

Sources & evidence

ORD record
ord-63e2fb8be3b04acd9e211e8e55574008
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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