Ethyl bromoacetate → [3-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-ylmethoxy]-acetic acid ethylester

HRID 1796652Notes

Reaction equation

[OH:1][CH2:2][C:3]1[C:4]([CH3:28])=[C:5]2[C:10]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:13]=3)=[C:9]([C:25]#[N:26])[CH:8]=[N:7][N:6]2[CH:27]=1.[CH2:29]([O:31][C:32](=[O:35])[CH2:33]Br)[CH3:30].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)(Cl)Cl>[CH2:29]([O:31][C:32](=[O:35])[CH2:33][O:1][CH2:2][C:3]1[C:4]([CH3:28])=[C:5]2[C:10]([NH:11][C:12]3[CH:13]=[CH:14][C:15]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:16][CH:17]=3)=[C:9]([C:25]#[N:26])[CH:8]=[N:7][N:6]2[CH:27]=1)[CH3:30]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-hydroxymethyl-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile (Example 3B) (36 mg, 0.097 mmol), bromo-acetic acid ethyl ester (24 mg, 0.146 mmol) and K2CO3 (67 mg, 0.48 mmol) in DMF (0.6 ml) was heated at 80° C. for 45 min, then diluted with CHCl3 (50 ml), washed with H2O (2×20 ml), dried with Na2SO4. Concentrated in vacuo and purified by prep. TLC to give the title compound (12.2 mg, 28%) (50% EtOAc—hexanes). It has a retention time of 6.62 min (standard LCl method, 8 min run). MS Found: (M+H)+=457.1

Workup

washwashed with H2O (2×20 ml)
dry with materialdried with Na2SO4
concentrationConcentrated in vacuo
custompurified by prep

Sources & evidence

ORD record: ord-74a4fdc92f6546fdb5241286e86af7bb
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030112B2

Reaction notes

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