Potassium Carbonate → HCID 11281004, compound

HRID 2297630Notes

Reaction equation

HRID 2297630 reaction equation
Cl[C:2]1[C:7]2[NH:8][C:9]([CH:11]([CH3:13])[CH3:12])=[N:10][C:6]=2[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-:15].[K+].[K+].Br[CH2:21][C:22]1[CH:31]=[C:30]2[C:25]([CH:26]=[CH:27][C:28]([C:32]3[N:36]=[C:35]([CH3:37])[O:34][N:33]=3)=[CH:29]2)=[CH:24][CH:23]=1>CN(C=O)C>[CH:11]([C:9]1[N:8]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]3[C:30](=[CH:29][C:28]([C:32]4[N:36]=[C:35]([CH3:37])[O:34][N:33]=4)=[CH:27][CH:26]=3)[CH:31]=2)[C:7]2[C:2](=[O:15])[NH:3][CH:4]=[CH:5][C:6]=2[N:10]=1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11220400HCID 11220400, compoundHCID 178439968HCID 178439968, compound

Product 1

HCID 11281004HCID 11281004, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of “AB” and 4-chloro-2-isopropyl-3H-imidazo[4,5-c]pyridine is found in the mother liquor. A solution of 0.877 g of “AB” and 0.691 g of potassium carbonate in 30 ml of DMF is stirred at room temperature for 30 minutes. 1.5 g of 3-(7-bromomethylnaphthalen-2-yl)-5-methyl[1,2,4]oxadiazole (m.p. 149-150°) are added and the mixture is stirred for 16 hours and worked up in the customary manner. After chromatography on silica gel, in addition to the two regioisomeric dialkylation products, the compound 2-isopropyl-3-[7-(5-methyl[1,2,4]oxadiazol-3-yl)naphth-2-ylmethyl]-5H-imidazo[4,5-c]pyridin-4-one (“BB”), m.p. 214-215° EI 399 is obtained

Workup

  1. additionAfter chromatography on silica gel, in addition to the two regioisomeric dialkylation products

Sources & evidence

ORD record
ord-d0a13e3872904f3c8ca735d3b698a594
Source dataset
uspto-grants-2002_12
Patent number
US06492384B1

Reaction notes

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