Trifluoroacetic acid → 3-Cyano-4-(3-hydroxymethyl-4-phenoxy-phenylamino)-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester

HRID 1796632Notes

Reaction equation

HRID 1796632 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:39])=[C:8]2[C:13]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:17]([CH2:28][O:29]C4CCCCO4)[CH:16]=3)=[C:12]([C:36]#[N:37])[CH:11]=[N:10][N:9]2[CH:38]=1)=[O:5])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:39])=[C:8]2[C:13]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:17]([CH2:28][OH:29])[CH:16]=3)=[C:12]([C:36]#[N:37])[CH:11]=[N:10][N:9]2[CH:38]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69327665HCID 69327665, compound

Product 1

HCID 696493093-Cyano-4-(3-hydroxymethyl-4-phenoxy-phenylamino)-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl esterYield 43.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 394 (30 mg, 0.057 mmol) in CH2Cl2 (1 ml) was added TFA (300 μl). The mixture was stirred at rt for 30 min, concentrated and purified by silica gel flash column chromatography to give the title compound (11 mg, 44%) (30% EtOAc—Hexanes). LCMS Found: (M+H)+=443.2

Workup

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

Sources & evidence

ORD record
ord-6a7f17bf4de14c848a51bc8bbf22276e
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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