Tetrahydrofuran → 6-Methylpyrazine-2-carboxylic acid

HRID 1942242Notes

Reaction equation

HRID 1942242 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].C[Mg+].[Br-].[CH2:38]1C[O:41]CC1>CCOCC>[CH3:30][C:26]1[N:25]=[C:24]([C:22]([OH:23])=[O:41])[CH:29]=[N:28][CH:27]=1.[OH:1][C:2]([CH3:38])([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

6

Reactant 3

HCID 8028TetrahydrofuranHCID 591610946-Methyl-pyrazine-2-carboxylic acid {3-[3-(2-oxo-propoxy)-benzoyl-amino]-adamantan-1-yl}-amideHCID 178418689HCID 178418689, compound

Product 2

HCID 4708976-Methylpyrazine-2-carboxylic acidHCID 591610666-Methyl-pyrazine-2-carboxylic acid {3-[3-(2-hydroxy-2-methylpropoxy)-benzoylamino]-adamantan-1-yl}-amide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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-2b3b634373dc41208eac09e2f9ddb1b7
Source dataset
uspto-grants-2013_03
Patent number
US08389519B2

Reaction notes

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