1,4-Pentadien-3-one → 3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-N-[(S)-6-(4-oxo-piperidin-1-yl)-4,5,6,7-tetrahydro-benzothiazol-2-yl]-benzamide

HRID 1468189

반응식

HRID 1468189 반응식
[CH:1]([C:3]([CH:5]=[CH2:6])=[O:4])=[CH2:2].[NH2:7][C@H:8]1[CH2:39][CH2:38][C:11]2[N:12]=[C:13]([NH:15][C:16](=[O:37])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][N:24]4[CH:28]=[C:27]([C:29]5[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][CH:30]=5)[CH:26]=[N:25]4)[CH:18]=3)[S:14][C:10]=2[CH2:9]1>C(Cl)Cl.CO>[C:35]([C:32]1[CH:31]=[CH:30][C:29]([C:27]2[CH:26]=[N:25][N:24]([CH2:23][C:19]3[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=3)[C:16]([NH:15][C:13]3[S:14][C:10]4[CH2:9][C@@H:8]([N:7]5[CH2:6][CH2:5][C:3](=[O:4])[CH2:1][CH2:2]5)[CH2:39][CH2:38][C:11]=4[N:12]=3)=[O:37])[CH:28]=2)=[CH:34][CH:33]=1)#[N:36]

참가 물질

5

반응물 2

HCID 5431991,4-Pentadien-3-oneHCID 56966525N-((S)-6-amino-4,5,6,7-tetrahydro-benzothiazol-2-yl)-3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzamide

생성물 1

HCID 569660823-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-N-[(S)-6-(4-oxo-piperidin-1-yl)-4,5,6,7-tetrahydro-benzothiazol-2-yl]-benzamide수율 30%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매2회

실험 절차

Add a solution of divinyl ketone (0.08 g 1.03 mmol) in 1 mL of CH2Cl2 to a solution of N—((S)-6-amino-4,5,6,7-tetrahydro-benzothiazol-2-yl)-3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzamide (0.47 g, 1.03 mmol) in 10 mL of CH2Cl2 and 10 mL of MeOH. Stir the solution for 3 h at room temperature and concentrate the mixture. Purify the residue via column chromatography eluting with 1-10% CH2Cl2/MeOH to give 0.16 g, 30% yield of 3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-N—[(S)-6-(4-oxo-piperidin-1-yl)-4,5,6,7-tetrahydro-benzothiazol-2-yl]-benzamide. Both 1 cms and NMR show that the product exists as a mixture of ketone and hydrate. MS, ES+ 555.70 (M+H2O+H), rt 1.21 min.

후처리

  1. concentrationconcentrate the mixture
  2. customPurify the residue via column chromatography
  3. washeluting with 1-10% CH2Cl2/MeOH

출처 및 근거

ORD 기록
ord-70caa8c509fc4d2d8a5457718d2c95ad
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000154B2

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