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

HRID 884802

反応式

HRID 884802 の反応式
[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

参加物

5

反応物 2

HCID 111676593-(5-amino-4-(3-iodobenzoyl)-1H-pyrazol-1-yl)-N-cyclopropyl-4-methylbenzamideHCID 178418546HCID 178418546、化合物

生成物 1

HCID 11338127Acumapimod収率 34%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-f9dc9bb8e1a6467789ad741dfca425c1
出典データセット
uspto-grants-2012_08
特許番号
US08242117B2

関連ノート

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