3-(5-amino-4-(3-iodobenzoyl)-1H-pyrazol-1-yl)-N-cyclopropyl-4-methylbenzamide → Acumapimod

HRID 1959523Notes

Reaction equation

HRID 1959523 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](I)[CH:22]=1.[C:29]([Cu])#[N:30]>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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]([C:29]#[N:30])[CH:22]=1

Participants

5

Reactant 2

HCID 111676593-(5-amino-4-(3-iodobenzoyl)-1H-pyrazol-1-yl)-N-cyclopropyl-4-methylbenzamideHCID 178418546HCID 178418546, compound

Product 1

HCID 11338127AcumapimodYield 34%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-[5-amino-4-(3-iodobenzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide (110 mg, 0.23 mmol) in DMF (5 mL) was added CuCN (40 mg, 0.45 mmol) and tetrakis(triphenylphosphine)palladium (catalytic) and the mixture was heated at 100° C. over night under N2. The solvent was removed and the residue was suspended in EtOAc, and solids were filtered off. The filtrate was washed by water, brine, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography on silica gel (EtOAc). Product was obtained as a beige solid (30 mg, 34%). HPLC (4 minute 10-90 gradient) tR 2.02 min; MS m/z 386.13 [M+H]+.

Workup

  1. customThe solvent was removed
  2. filtrationsolids were filtered off
  3. washThe filtrate was washed by water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography on silica gel (EtOAc)

Sources & evidence

ORD record
ord-eb7efd3e8882493a906747516afb59dc
Source dataset
uspto-grants-2013_04
Patent number
US08410160B2

Reaction notes

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