HCID 66589717, compound → HCID 178428222, compound

HRID 1091818Notes

Reaction equation

HRID 1091818 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([CH:12]2[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[SH:8].[Cl:15][C:16]1[N:21]=[C:20](S(C)(=O)=O)[N:19]=[C:18]([NH:26][C:27]2[NH:31][N:30]=[C:29]([CH3:32])[CH:28]=2)[CH:17]=1>C(O)(C)(C)C.CCOC(C)=O>[CH3:32][C:29]1[CH:28]=[C:27]([NH:26][C:18]2[CH:17]=[C:16]([Cl:15])[N:21]=[C:20]([S:8][C:7]3[CH:6]=[CH:5][C:4]([NH:9][C:10]([CH:12]4[CH2:13][CH2:14]4)=[O:11])=[CH:3][C:2]=3[F:1])[N:19]=2)[NH:31][N:30]=1

Participants

5

Reactant 2

HCID 66589717HCID 66589717, compoundHCID 178428229HCID 178428229, compound

Product 1

HCID 178428222HCID 178428222, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(3-fluoro-4-mercaptophenyl)cyclopropane-carboxamide (1.0 g, 4.8 mmol) and 6-chloro-N-(3-methyl-1H-pyrazol-5-yl)-2-(methylsulfonyl)pyrimidin-4-amine (1.4 g, 4.8 mmol) in t-butanol (10 ml) was heated 70° C. for 18 h. Reaction mixture cooled to room temperature then diluted with EtOAc (60 ml), washed with sat. NaHCO3 solution (30 ml), brine (30 ml), dried (MgSO4), filtered and concentrated in vacuo. Crude product was purified by flash chromatography on silica (EtOAc/Petrol 20 to 60%) to give the title compound as white solid (800 mg, 40%). ES+ 419.

Workup

  1. customReaction mixture
  2. washwashed with sat. NaHCO3 solution (30 ml), brine (30 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customCrude product was purified by flash chromatography on silica (EtOAc/Petrol 20 to 60%)

Sources & evidence

ORD record
ord-75f0a6283194458b8329299983f97ee1
Source dataset
uspto-grants-2012_03
Patent number
US08129399B2

Reaction notes

Loading…