Acetamide → 4-Piperidinopiperidine-1-carbonyl chloride

HRID 1037627노트

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HRID 1037627 반응식
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

참가 물질

6

반응물 4

HCID 178AcetamideHCID 1049PyridineHCID 6344Dichloromethane2회HCID 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

생성물 1

HCID 98133754-Piperidinopiperidine-1-carbonyl chloride

시약·촉매·용매 1

HCID 8471Triethylamine용매

반응 조건

온도
35 °C

실험 절차

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%

후처리

  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

출처 및 근거

ORD 기록
ord-6518246a8d4847cfa3c153f2d56092e4
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546573B2

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