(4-Aminophenoxy)benzene → 3-Cyano-5-methoxy-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester

HRID 1796626Notes

Reaction equation

HRID 1796626 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:18][CH3:19])=[C:8]2[C:13](Cl)=[C:12]([C:15]#[N:16])[CH:11]=[N:10][N:9]2[CH:17]=1)=[O:5])[CH3:2].[O:20]([C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.COC(C1C(C)=C2C(NC3C=CC(OC4C=CC=CC=4OC(C(OC(C)(C)C)=O)(C)C)=CC=3)=C(C#N)C=NN2C=1)=O.C(OC(C1C(OC)=C2C(O)=C(C#N)C=NN2C=1)=O)C>>[CH2:1]([O:3][C:4]([C:6]1[C:7]([O:18][CH3:19])=[C:8]2[C:13]([NH:33][C:30]3[CH:29]=[CH:28][C:27]([O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:32][CH:31]=3)=[C:12]([C:15]#[N:16])[CH:11]=[N:10][N:9]2[CH:17]=1)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 8764(4-Aminophenoxy)benzeneHCID 22179696HCID 22179696, compoundHCID 693275004-Chloro-3-cyano-5-methoxy-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl esterHCID 178469451HCID 178469451, compound

Product 1

HCID 693274533-Cyano-5-methoxy-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl esterYield 50.3%

Procedure

The compound 393 was prepared from 0.37 g of crude 4-chloro-3-cyano-5-methoxy-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester and 4-phenoxy-phenylamine (0.24 g, 1.30 mmol) by a route analogous to that used for the preparation of compound 388D. 0.28 g of 393 was obtained in 49% yield for 3 steps from 393F. LCMS Found: (M+H)+=429.

Sources & evidence

ORD record
ord-a5c0d5ebf88a477f952185303c181f5b
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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