Dichloromethane → 5,6-Dimethoxy-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile

HRID 1796639Notes

Reaction equation

HRID 1796639 reaction equation
[OH:1][C:2]1[C:3]([O:27][CH3:28])=[C:4]2[C:9]([NH:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][CH:12]=3)=[C:8]([C:24]#[N:25])[CH:7]=[N:6][N:5]2[CH:26]=1.S(OC)(O[CH3:33])(=O)=O.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>CC(C)=O>[CH3:28][O:27][C:3]1[C:2]([O:1][CH3:33])=[CH:26][N:5]2[C:4]=1[C:9]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:16]=1)=[C:8]([C:24]#[N:25])[CH:7]=[N:6]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 221796556-Hydroxy-5-methoxy-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile

Product 1

HCID 221796025,6-Dimethoxy-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrileYield 88.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of compound from Example 399 (14 mg, 0.038 mmol), dimethyl sulfate (4 μl, 0.042 mmol), K2CO3 (14 mg, 0.101 mmol) in acetone (0.5 ml) was stirred at rt overnight. After regular workup, the title compound (13 mg, 88%) was obtained after silica gel flash column chromatography (100% CH2Cl2). LCMS Found: (M+H)+=387.1

Sources & evidence

ORD record
ord-6c8d19d4128445d29015e5c3110982b9
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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