3,3-Difluoroazetidine hydrochloride → 6-Cyclopropylmethoxy-5-trifluoromethyl-pyridine-2-carboxylic acid [1-(3,3-difluoro-azetidine-1-carbonyl)-1-ethyl-propyl]-amide

HRID 632383Notes

Reaction equation

HRID 632383 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([NH:14][C:15]([CH2:21][CH3:22])([CH2:19][CH3:20])[C:16](O)=[O:17])=[O:13])[CH:9]=[CH:8][C:7]=2[C:23]([F:26])([F:25])[F:24])[CH2:3][CH2:2]1.Cl.[F:28][C:29]1([F:33])[CH2:32][NH:31][CH2:30]1>>[F:28][C:29]1([F:33])[CH2:32][N:31]([C:16]([C:15]([NH:14][C:12]([C:10]2[CH:9]=[CH:8][C:7]([C:23]([F:24])([F:26])[F:25])=[C:6]([O:5][CH2:4][CH:1]3[CH2:2][CH2:3]3)[N:11]=2)=[O:13])([CH2:19][CH3:20])[CH2:21][CH3:22])=[O:17])[CH2:30]1

Participants

3

Reactant 2

HCID 27582473,3-Difluoroazetidine hydrochlorideHCID 710874622-(6-(Cyclopropylmethoxy)-5-(trifluoromethyl)picolinamido)-2-ethylbutanoic acid

Product 1

HCID 711056996-Cyclopropylmethoxy-5-trifluoromethyl-pyridine-2-carboxylic acid [1-(3,3-difluoro-azetidine-1-carbonyl)-1-ethyl-propyl]-amide

Procedure

In analogy to the procedure described in Example 293, 2-[(6-cyclopropylmethoxy-5-trifluoromethyl-pyridine-2-carbonyl)-amino]-2-ethyl-butyric acid (Example 252 b) and 3,3-difluoroazetidine hydrochloride (CAN 288315-03-7) were condensed to the title product. MS (EI): m/e=450.0 [M+H]+.

Sources & evidence

ORD record
ord-f75e2e24f39747f384ca6d4808f36ec6
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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