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

HRID 1796642Notes

Reaction equation

HRID 1796642 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[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:18]([C:25]1[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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>>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13]([NH:31][C:28]3[CH:27]=[CH:26][C:25]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:30][CH:29]=3)=[C:12]([C:15]#[N:16])[CH:11]=[N:10][N:9]2[CH:17]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 8764(4-Aminophenoxy)benzeneHCID 22179696HCID 22179696, compoundHCID 69326995Ethyl 4-chloro-3-cyanopyrrolo[1,2-b]pyridazine-6-carboxylate

Product 1

HCID 696492943-Cyano-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl esterYield 53%

Procedure

Compound 403 was prepared from 403C and 4-phenoxy-phenylamine by a route analogous to that used for the preparation of 388D. Yield: 53%. MS Found: (M+H)+=399.2; 1H NMR (CDCl3) δ 8.1 and 7.9 (s, 1H each), 7.3 (m, 2H), 7.26 (m, 2H), 7.2 (m, 2H), 7.15 (m, 4H), 6.2 (s, 1H), 4.25 (q, J=7.2 Hz, 2H), 1.32 (t, J=7.2 Hz, 3H).

Sources & evidence

ORD record
ord-f0e4f803fd9343e9836a11f053f459fb
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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