Methyl iodide → 5-Cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-pyridine-2-carboxylic acid [cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-methyl-amide

HRID 624893Notes

Reaction equation

HRID 624893 reaction equation
[CH:1]1([CH:4]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[CH2:22][CH2:21]3)=[C:16]([O:23][CH2:24][CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[N:15]=2)=[O:13])[C:5]2[N:9]=[C:8]([CH3:10])[O:7][N:6]=2)[CH2:3][CH2:2]1.[CH3:31]I.[H-].[Na+]>>[CH:1]1([CH:4]([N:11]([CH3:31])[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[CH2:22][CH2:21]3)=[C:16]([O:23][CH2:24][CH:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)[N:15]=2)=[O:13])[C:5]2[N:9]=[C:8]([CH3:10])[O:7][N:6]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 711056515-Cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-pyridine-2-carboxylic acid [cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-amide

Product 1

HCID 902153255-Cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-pyridine-2-carboxylic acid [cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-methyl-amide

Procedure

In analogy to the procure described in Example 16 b), 5-cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-pyridine-2-carboxylic acid [cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-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=427.2 [MH]+.

Sources & evidence

ORD record
ord-e8936f7d1da54f2ba9722fa725e90701
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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