Potassium Carbonate → 3-{5-Amino-4-[3-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-benzoyl]-pyrazol-1-yl}-N-cyclopropyl-4-methyl-benzamide

HRID 1959537Notes

Reaction equation

HRID 1959537 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:15][CH2:14]2)=[O:11])[N:5]=[CH:4][C:3]=1[C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=1.Cl[CH2:30][CH:31]1[CH2:35][O:34][C:33]([CH3:37])([CH3:36])[O:32]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:14][CH2:15]2)=[O:11])[N:5]=[CH:4][C:3]=1[C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:30][CH:31]2[CH2:35][O:34][C:33]([CH3:37])([CH3:36])[O:32]2)[CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 203744-(Chloromethyl)-2,2-dimethyl-1,3-dioxolaneHCID 112458363-[5-amino-4-(3-hydroxy-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide

Product 1

HCID 580889863-{5-Amino-4-[3-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-benzoyl]-pyrazol-1-yl}-N-cyclopropyl-4-methyl-benzamideYield 18.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a stirred solution of 3-[5-amino-4-(3-hydroxy-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide (75 mg, 0.2 mmol) and 4-chloromethyl-2,2-dimethyl-[1,3]dioxolane (36 mg, 0.24 mmol) were dissolved in DMF (4 ml) was added K2CO3 and the mixture stirred at 150° C. for 2 h in microwave oven. The solvent was removed, residue was dissolved in EtOAc, washed by water, brine, dried over Na2SO4, and concentrated. The residue was purified by column chromatography (EtOAc:Hex=3:1) and the product was obtained as a colorless oil (18 mg, 18%). HPLC (4 minute gradient) tR 2.57 min; MS m/z 491.11 [M+H]+.

Workup

  1. customThe solvent was removed
  2. dissolutionresidue was dissolved in EtOAc
  3. washwashed by water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (EtOAc:Hex=3:1)

Sources & evidence

ORD record
ord-5ed7e1b5b14f4c33906535d1d11c1d11
Source dataset
uspto-grants-2013_04
Patent number
US08410160B2

Reaction notes

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