Sodium hydride → 2,2-Dimethyl-4-(1-methyl-1,6-dihydro-6-oxo-3-pyridazinyl-amino)-6-cyano-3chromanol

HRID 2255046Notes

Reaction equation

HRID 2255046 reaction equation
[CH3:1][C:2]1([CH3:15])[CH:11]2[O:12][CH:10]2[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]#[N:14])[CH:8]=2)[O:3]1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20](=[O:23])[N:19]([CH3:24])[N:18]=1.[H-].[Na+]>CS(C)=O>[CH3:1][C:2]1([CH3:15])[CH:11]([OH:12])[CH:10]([NH:16][C:17]2[CH:22]=[CH:21][C:20](=[O:23])[N:19]([CH3:24])[N:18]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]#[N:14])[CH:8]=2)[O:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochromanHCID 157119126-Amino-2-methyl-2,3-dihydropyridazin-3-one

Product 1

HCID 99492442,2-Dimethyl-4-(1-methyl-1,6-dihydro-6-oxo-3-pyridazinyl-amino)-6-cyano-3chromanol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.0 g of 2,2-dimethyl-3,4-epoxy-6-cyanochroman ("IIa") are added to a mixture of 1.2 g of 3-amino-1-methyl-1,6-dihydropyridazin-6-one and 0.3 g of NaH (80% strength) in 50 ml of dimethyl sulfoxide (DMSO) at 25°, and the mixture is stirred for 4 hours. Customary working-up and purification by column chromatography (ethyl acetate/methanol) give 2,2-dimethyl-4-(1-methyl-1,6-dihydro-6-oxo-3-pyridazinyl-amino)-6-cyano-3chromanol, m.p. 117°-119°.

Workup

  1. custompurification by column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-974faf64399e4504babfa6a4636dc1c1
Source dataset
uspto-grants-1993_08
Patent number
US05238937

Reaction notes

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