Methyl iodide → 6-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid [(S)-2-cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-methyl-amide

HRID 624891Notes

Reaction equation

HRID 624891 reaction equation
[CH:1]1([CH2:4][C@H:5]([NH:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:24][C:23]([F:26])([F:25])[CH2:22]3)=[C:17]([O:27][CH2:28][CH:29]3[CH2:31][CH2:30]3)[N:16]=2)=[O:14])[C:6]2[N:10]=[C:9]([CH3:11])[O:8][N:7]=2)[CH2:3][CH2:2]1.[CH3:32]I.[H-].[Na+]>>[CH:1]1([CH2:4][C@H:5]([N:12]([CH3:32])[C:13]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:22][C:23]([F:25])([F:26])[CH2:24]3)=[C:17]([O:27][CH2:28][CH:29]3[CH2:31][CH2:30]3)[N:16]=2)=[O:14])[C:6]2[N:10]=[C:9]([CH3:11])[O:8][N:7]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 711056176-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid [(S)-2-cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide

Product 1

HCID 1184586316-Cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid [(S)-2-cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-methyl-amide

Procedure

In analogy to the procure described in Example 16 b), 6-cyclopropylmethoxy-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid [(S)-2-cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethyl]-amide was reacted with methyl iodide (CAN 74-88-4) in the presence of sodium hydride to give the title compound as colorless oil; MS (EI): m/e=448.2 [MH]+.

Sources & evidence

ORD record
ord-842365e9fd1746d0bf37209ef0ea9ad2
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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