Potassium Carbonate → 1-Benzyl-5'-oxo-2'-(4-phenoxyphenyl)-5',6'-dihydro-4'H-spiro[piperidine-4,7'-pyrazolo[1,5-a]pyrimidine]-3'-carbonitrile

HRID 64310

反応式

HRID 64310 の反応式
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:9][CH:8]=2)[C:3]=1[C:20]#[N:21].[CH2:22]([N:29]1[CH2:34][CH2:33][C:32](=[CH:35][C:36](OCC)=[O:37])[CH2:31][CH2:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:22]([N:29]1[CH2:30][CH2:31][C:32]2([N:6]3[N:5]=[C:4]([C:7]4[CH:8]=[CH:9][C:10]([O:13][C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)=[CH:11][CH:12]=4)[C:3]([C:20]#[N:21])=[C:2]3[NH:1][C:36](=[O:37])[CH2:35]2)[CH2:33][CH2:34]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 10377866Ethyl 2-(1-benzylpiperidin-4-ylidene)acetateHCID 178509389HCID 178509389、化合物

生成物 1

HCID 1369837931-Benzyl-5'-oxo-2'-(4-phenoxyphenyl)-5',6'-dihydro-4'H-spiro[piperidine-4,7'-pyrazolo[1,5-a]pyrimidine]-3'-carbonitrile収率 54.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carbonitrile (1.0 g, 3.6 mmol), ethyl 2-(1-benzylpiperidin-4-ylidene)acetate (1.1 g, 4.3 mmol) and K2CO3 (745 mg, 5.4 mmol) in DMF (20 mL) was heated to 80° C. for 16 hr under N2. The reaction was quenched with water (20 mL) and extracted with EA (20 mL×3). The combined organic layers were dried over Na2SO4, concentrated and purified by chromatography column on silica gel using 30% of EA in PE as eluant to give the product (950 mg, 54.9%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 11.92 (s, 1H), 7.84 (d, J=8.8 Hz, 2H), 7.48-7.40 (m, 2H), 7.36-7.29 (m, 4H), 7.27-7.23 (m, 1H), 7.20 (t, J=7.6 Hz, 1H), 7.15-7.07 (m, 4H), 3.55 (s, 2H), 3.01 (s, 2H), 2.81-2.73 (m, 2H), 2.39-2.27 (m, 2H), 2.26-2.16 (m, 2H), 1.83-1.74 (m, 2H). MS (ESI, m/e) [M+1]+ 489.9.

後処理

  1. customThe reaction was quenched with water (20 mL)
  2. extractionextracted with EA (20 mL×3)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by chromatography column on silica gel using 30% of EA in PE as eluant

出典と根拠

ORDレコード
ord-808905ad54ce43d5a58d73a27bf6f506
出典データセット
uspto-grants-2016_09
特許番号
US09447106B2

関連ノート

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