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

反応式

[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]

参加物

実験手順

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.

後処理

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

出典と根拠

ORDレコード: ord-70caa8c509fc4d2d8a5457718d2c95ad
出典データセット: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09000154B2

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 2

実験手順

後処理

出典と根拠

関連ノート