4-methyl-2-[6-((E)-3-phenyl-propenyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide → 4-Methyl-2-[6-(3-phenyl-propyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide

HRID 1879143ノート

反応式

HRID 1879143 の反応式
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[N:20][CH:19]=[C:18](/[CH:22]=[CH:23]/[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:17]=2)=[N:13][C:12]=1[CH3:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[N:20][CH:19]=[C:18]([CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:17]=2)=[N:13][C:12]=1[CH3:31])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 1

HCID 684877744-methyl-2-[6-((E)-3-phenyl-propenyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide

生成物 1

HCID 594895384-Methyl-2-[6-(3-phenyl-propyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide収率 60%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

Part B. To a solution of 4-methyl-2-[6-((E)-3-phenyl-propenyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide (39 mg, 0.09 mmol, 1.0 equiv) in ethyl acetate was added Pd/C (15 mg, 10%). The flask was first purged with nitrogen, then with hydrogen. The reaction mixture was stirred at ambient temperature for 60 hr and monitored by LCMS. Upon completion, the reaction mixture was diluted with ethyl acetate, filtered through Celite and concentrated in vacuo. The crude product was purified by prep HPLC (acetonitrile/water, 0.1% trifluoroacetic acid) to afford 4-methyl-2-[6-(3-phenyl-propyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide (19 mg, 60%). 1H NMR (400 MHz, CD2Cl2) δ 9.14 (s, 1H), 9.12 (s, 1H), 7.14-7.36 (m, 10H), 6.23 (bs, 1H), 4.59 (d, J=8.0 Hz, 2H), 2.86 (t, J=8.0 Hz, 2H), 2.72 (s, 3H), 2.69-2.72 (m, 2H), 2.07-2.15 (m, 21-1); HRMS (M+H)+=429.17.

後処理

  1. customThe flask was first purged with nitrogen
  2. additionUpon completion, the reaction mixture was diluted with ethyl acetate
  3. filtrationfiltered through Celite
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by prep HPLC (acetonitrile/water, 0.1% trifluoroacetic acid)

出典と根拠

ORDレコード
ord-d6d880feda7743e6b97565f51db3612d
出典データセット
uspto-grants-2012_11
特許番号
US08314138B2

反応ノート

読み込み中…