2-(Tributylstannyl)pyrazine → 3-[5-Amino-4-(3-pyrazin-2-yl-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide

HRID 251369

反応式

HRID 251369 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([Sn](CCCC)(CCCC)[C:34]1[CH:39]=[N:38][CH:37]=[CH:36][N:35]=1)CCC>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=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:34]2[CH:39]=[N:38][CH:37]=[CH:36][N:35]=2)[CH:22]=1

参加物

5

反応物 2

HCID 27373162-(Tributylstannyl)pyrazineHCID 111676593-(5-amino-4-(3-iodobenzoyl)-1H-pyrazol-1-yl)-N-cyclopropyl-4-methylbenzamide

生成物 1

HCID 113964923-[5-Amino-4-(3-pyrazin-2-yl-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methylbenzamide収率 5.2%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
160 °C

実験手順

To a stirred solution of 3-[5-amino-4-(3-iodo-benzoyl)-pyrazol -1-yl]-N-cyclopropyl-4-methylbenzamide (130 mg, 0.27 mmol) and 2-tributylstannylpyrazine (119 mg, 0.32 mmol) in DMF (2 mL) was added tetrakis(triphenylphosphine) palladium (catalytic) and the mixture was heated in microwave at 160° C. for 15 min. The solvent was removed and the residue was dissolved in EtOAc. The organics were washed by water, brine and concentrated. The crude material was purified by preparatory HPLC to provide the desired product as beige solid (6.2 mg, 5%). HPLC (4 minute 10-90 gradient) tR 2.12 min; MS m/z 439.19 [M+H]+.

後処理

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe organics were washed by water, brine
  4. concentrationconcentrated
  5. customThe crude material was purified by preparatory HPLC

出典と根拠

ORDレコード
ord-9df02e7ed1d64bc091fc26a838c8ba8b
出典データセット
uspto-grants-2011_01
特許番号
US07863314B2

関連ノート

読み込み中…