Acetamide → 4-Piperidinopiperidine-1-carbonyl chloride

HRID 1037627

反応式

HRID 1037627 の反応式
CCC1C=CC(=O)[C:5]2=C[C:7]3[CH2:25][N:24]4[C:10](=[CH:11][C:12]5[C@@](O)(CC)C(=O)OC[C:13]=5[C:22]4=O)[C:8]=3[NH:9][C:4]=12.[CH2:30]([Cl:32])Cl.C(N)(=[O:35])C.N1C=CC=CC=1>C(N(CC)CC)C>[N:24]1([CH:25]2[CH2:5][CH2:4][N:9]([C:30]([Cl:32])=[O:35])[CH2:8][CH2:7]2)[CH2:22][CH2:13][CH2:12][CH2:11][CH2:10]1

参加物

6

反応物 4

HCID 178AcetamideHCID 1049PyridineHCID 6344Dichloromethane2 回HCID 178436639(19S)-5,19-diethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),4,6,9,15(20)-hexaene-8,14,18-trione

生成物 1

HCID 98133754-Piperidinopiperidine-1-carbonyl chloride

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

反応条件

温度
35 °C

実験手順

In a suitable vessel were charged 7-Ethyl-10-hydroxycamptothecin (20 g), methylene dichloride, acetamide (3 gm) and pyridine (60 ml) under nitrogen atmosphere. A solution of [1,4′]bipiperidinyl-1′-carbonyl chloride (17.6 g), methylene dichloride and triethylamine (20 ml) was prepared and added to the above suspension and stirred at 30-40° C. for 2 hours. The solvent was distilled out under reduced pressure at 50° C. and hexane was added under stirring as an antisolvent to isolate crystalline compound. The crystalline compound was filtered, washed with hexane and dried under reduced pressure at 50° C. The yield was 28.4 g (95%). HPLC Purity—99.9%

後処理

  1. additionadded to the above suspension
  2. distillationThe solvent was distilled out under reduced pressure at 50° C.
  3. additionhexane was added
  4. stirringunder stirring as an antisolvent
  5. customto isolate crystalline compound
  6. filtrationThe crystalline compound was filtered
  7. washwashed with hexane
  8. customdried under reduced pressure at 50° C

出典と根拠

ORDレコード
ord-6518246a8d4847cfa3c153f2d56092e4
出典データセット
uspto-grants-2013_10
特許番号
US08546573B2

関連ノート

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