HCID 21025143, compound → 4-(4-{2-[1-(Carboxymethyl-carbamoyl)-1-methyl-ethoxy]-phenoxy}-phenylamino)-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester

HRID 1796619Notes

Reaction equation

HRID 1796619 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:45])=[C:7]2[C:12]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][C:28]([C:31](=[O:41])[NH:32][CH2:33][C:34]([O:36]C(C)(C)C)=[O:35])([CH3:30])[CH3:29])=[CH:16][CH:15]=3)=[C:11]([C:42]#[N:43])[CH:10]=[N:9][N:8]2[CH:44]=1)=[O:4]>C(O)(C(F)(F)F)=O.C(Cl)Cl.O>[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:45])=[C:7]2[C:12]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][C:28]([C:31](=[O:41])[NH:32][CH2:33][C:34]([OH:36])=[O:35])([CH3:30])[CH3:29])=[CH:16][CH:15]=3)=[C:11]([C:42]#[N:43])[CH:10]=[N:9][N:8]2[CH:44]=1)=[O:4]

Participants

3

Reactant 1

HCID 21025143HCID 21025143, compound

Product 1

HCID 210250354-(4-{2-[1-(Carboxymethyl-carbamoyl)-1-methyl-ethoxy]-phenoxy}-phenylamino)-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl esterYield 87.8%

Reagents, catalysts & solvents 1

HCID 18672661TFA dichloromethane waterSolvent

Procedure

A solution of ester 388 (292 mg, 0.476 mmol) in TFA/CH2Cl2/H2O (5 ml, 48/48/4) was stirred for 2 h at rt, concentrated and purified by silica gel flash column chromatography to afford the title compound (233 mg, 89%) as a crystalline yellow powder (4%-12% MeOH—CH2Cl2). LCMS Found: (M+H)+=558.0

Workup

  1. concentrationconcentrated
  2. custompurified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-3d9d7bfd972e4f1ea6ece9ba9b4c6e95
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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