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 1879143노트

반응식

HRID 1879143 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d6d880feda7743e6b97565f51db3612d
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314138B2

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