6-Methyl-pyrazine-2-carboxylic acid {3-[3-(2-oxo-propoxy)-benzoyl-amino]-adamantan-1-yl}-amide → 6-Methyl-pyrazine-2-carboxylic acid {3-[3-(2-hydroxy-2-methylpropoxy)-benzoylamino]-adamantan-1-yl}-amide

HRID 218034Notes

Reaction equation

HRID 218034 reaction equation
[O:1]=[C:2]([CH3:34])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:31]=[CH:32][CH:33]=1)[C:8]([NH:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][C:13]([NH:21][C:22]([C:24]4[CH:29]=[N:28][CH:27]=[C:26]([CH3:30])[N:25]=4)=[O:23])([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:9].[CH3:35][Mg+].[Br-]>C1COCC1.CCOCC>[OH:1][C:2]([CH3:35])([CH3:34])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:31]=[CH:32][CH:33]=1)[C:8]([NH:10][C:11]12[CH2:18][CH:17]3[CH2:16][CH:15]([CH2:14][C:13]([NH:21][C:22]([C:24]4[CH:29]=[N:28][CH:27]=[C:26]([CH3:30])[N:25]=4)=[O:23])([CH2:19]3)[CH2:12]1)[CH2:20]2)=[O:9]

Participants

5

Reactant 2

HCID 591610946-Methyl-pyrazine-2-carboxylic acid {3-[3-(2-oxo-propoxy)-benzoyl-amino]-adamantan-1-yl}-amideHCID 178418689HCID 178418689, compound

Product 1

HCID 591610666-Methyl-pyrazine-2-carboxylic acid {3-[3-(2-hydroxy-2-methylpropoxy)-benzoylamino]-adamantan-1-yl}-amide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 6-methyl-pyrazine-2-carboxylic acid {3-[3-(2-oxo-propoxy)-benzoyl-amino]-adamantan-1-yl}-amide with MeMgBr in THF or ether at 0° C. could yield the title compound, 6-methyl-pyrazine-2-carboxylic acid {3-[3-(2-hydroxy-2-methylpropoxy)-benzoylamino]-adamantan-1-yl}-amide.

Sources & evidence

ORD record
ord-d0512a996ac74345a3ce2bbec0ae3e74
Source dataset
uspto-grants-2012_06
Patent number
US08198275B2

Reaction notes

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