Benzyl Chloride → 6-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid benzyl-(1-trifluoromethyl-cyclopropyl)-amide

HRID 624875Notes

Reaction equation

HRID 624875 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([NH:14][C:15]3([C:18]([F:21])([F:20])[F:19])[CH2:17][CH2:16]3)=[O:13])[CH:9]=[CH:8][C:7]=2[N:22]2[CH2:25][C:24]([F:27])([F:26])[CH2:23]2)[CH2:3][CH2:2]1.Cl[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[H-].[Na+]>>[CH2:29]([N:14]([C:15]1([C:18]([F:21])([F:20])[F:19])[CH2:16][CH2:17]1)[C:12]([C:10]1[CH:9]=[CH:8][C:7]([N:22]2[CH2:25][C:24]([F:27])([F:26])[CH2:23]2)=[C:6]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)[N:11]=1)=[O:13])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 71105762HCID 71105762, compound

Product 1

HCID 762835806-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid benzyl-(1-trifluoromethyl-cyclopropyl)-amide

Procedure

In analogy to the procedure described in Example 16 b), 6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)-N-(1-(trifluoromethyl)cyclopropyl)picolinamide (Example 16 a) was reacted with (chloromethyl)benzene (CAN 27987-13-9) in the presence of sodium hydride to give the title compound as colorless oil; MS (EI): m/e=482.4 [MH]+.

Sources & evidence

ORD record
ord-38cd6ea9dc194b78ad6d8d69cd820c05
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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