Pyrazole → 2-[2-(4-Cyclobutylpiperazin-1-Yl)-2-Oxoethyl]-6-(1H-Pyrazol-1-Yl)-1,2,3,4-Tetrahydroisoquinoline

HRID 1713102ノート

反応式

HRID 1713102 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([CH2:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([CH:21]3[CH2:24][CH2:23][CH2:22]3)[CH2:17][CH2:16]1)=[O:14])[CH2:6][CH2:5]2.[NH:25]1[CH:29]=[CH:28][CH:27]=[N:26]1.C(=NO)C1C(=CC=CC=1)O.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[CH:21]1([N:18]2[CH2:19][CH2:20][N:15]([C:13](=[O:14])[CH2:12][N:7]3[CH2:6][CH2:5][C:4]4[C:9](=[CH:10][CH:11]=[C:2]([N:25]5[CH:29]=[CH:28][CH:27]=[N:26]5)[CH:3]=4)[CH2:8]3)[CH2:16][CH2:17]2)[CH2:24][CH2:23][CH2:22]1

参加物

6

反応物 4

HCID 1048PyrazoleHCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 574205706-Bromo-2-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinoline

生成物 1

HCID 247515112-[2-(4-Cyclobutylpiperazin-1-Yl)-2-Oxoethyl]-6-(1H-Pyrazol-1-Yl)-1,2,3,4-Tetrahydroisoquinoline

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
120 °C

実験手順

A mixture of 6-bromo-2-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-1,2,3,4-tetrahydroisoquinoline (120 mg, 0.307 mmol), pyrazole (31 mg, 0.46 mmol), Cu2O (4 mg, 0.03 mmol), salicylaldoxime (16 mg, 0.12 mmol) and Cs2CO3 (300 mg, 0.92 mmol) in CH3CN (8 mL) is degassed by argon and heated at 120° C. in a sealed tube overnight. EtOAc (10 mL) is added and the mixture is filtered. The organic layer is washed with brine (10 mL) and dried. Purification of the residue by PTLC gives title compound as a light yellow solid. MS (M+1): 380.2; 1H NMR (δ, CDCl3): 7.88 (d, 1H), 7.70 (d, 1H), 7.47 (d, 1H), 7.41 (dd, 1H), 7.08 (d, 1H), 6.45 (dd, 1H), 3.71 (s, 2H), 3.65 (t, 4H), 3.38 (s, 2H), 2.96 (t, 2H), 2.81 (t, 2H), 2.63-2.72 (m, 1H), 2.28 (q, 4H), 1.64-2.08 (m, 6H).

後処理

  1. customis degassed by argon
  2. additionEtOAc (10 mL) is added
  3. filtrationthe mixture is filtered
  4. washThe organic layer is washed with brine (10 mL)
  5. customdried
  6. customPurification of the residue by PTLC

出典と根拠

ORDレコード
ord-3fbd91f6ea6d45cb85018dcf3abc12ce
出典データセット
uspto-grants-2010_09
特許番号
US07795262B2

反応ノート

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