Potassium Carbonate → HCID 22179696, compound

HRID 1796617Notes

Reaction equation

HRID 1796617 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:17])=[C:7]2[C:12](Cl)=[C:11]([C:14]#[N:15])[CH:10]=[N:9][N:8]2[CH:16]=1)=[O:4].[C:18]([O:22][C:23](=[O:42])[C:24]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][C:35]1[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=1)([CH3:26])[CH3:25])([CH3:21])([CH3:20])[CH3:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:6]([CH3:17])=[C:7]2[C:12]([NH:41][C:38]3[CH:39]=[CH:40][C:35]([O:34][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[O:27][C:24]([C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:42])([CH3:26])[CH3:25])=[CH:36][CH:37]=3)=[C:11]([C:14]#[N:15])[CH:10]=[N:9][N:8]2[CH:16]=1)=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 210251742-[2-(4-Amino-phenoxy)-phenoxy]-2-methyl-propionic acid tert-butyl esterHCID 69327667HCID 69327667, compound

Product 1

HCID 22179696HCID 22179696, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chloro-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester (prepared using the procedure of Example 1D) (320 mg, 1.28 mmol), aniline 388C (440 mg, 1.28 mmol) and K2CO3 (1.77 g, 12.8 mmol) in anhydrous DMF (8 ml) was stirred at rt for 16 h. After regular workup, the residue was purified by silica gel flash column chromatography to afford 388D (651 mg, 91%) as a faintly yellow solid (0%-4% EtOAc—CH2Cl2). LCMS Found: (M+H)+=556.8; (M−tBu+2H)+=500.9

Workup

  1. customprepared
  2. customAfter regular workup, the residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-02cdab12942c4f53809d9bc0de5ef5a8
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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