Potassium Carbonate → (4R)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole-6carboxylic hydrazide

HRID 1289904노트

반응식

HRID 1289904 반응식
I[C:2]1[CH:10]=[CH:9][C:8]2[NH:7][CH:6]=[C:5]3[CH2:11][C@H:12]([N:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])[CH2:13][C:3]=1[C:4]=23.[OH:21][C:22]1C=CC=C[N:23]=1.C(=O)([O-])[O-].[K+].[K+].O.[NH2:35]N>C(#N)C.C(Cl)Cl>[CH2:15]([N:14]([CH2:18][CH2:19][CH3:20])[C@H:12]1[CH2:11][C:5]2=[CH:6][NH:7][C:8]3=[CH:9][CH:10]=[C:2]([C:22]([NH:23][NH2:35])=[O:21])[C:3](=[C:4]23)[CH2:13]1)[CH2:16][CH3:17]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 10691283(4S)-6-iodo-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indoleHCID 178516071HCID 178516071, 화합물

생성물 1

HCID 70284014(4R)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole-6carboxylic hydrazide

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 5.0 g (13.1 mmol) of (4S)-6-iodo-4-(di-n-propylamino)-1,3,4, 5-tetrahydrobenz [cd] indole in 250 ml of acetonitrile was added 3.5 g (37 mmol) of 2-hydroxypyridine, 16.9 g (122 mmol) of powdered potassium carbonate, and 0.30 g (0.26 mmol) of tetrakis (triphenylphosphine)palladium. The resultant mixture was heated at 65° C. under a carbon monoxide atmosphere for 14 hours. The cooled mixture was then treated with 2 ml of hydrazine hydrate and stirred for another 15 hours. After filtering, the mixture was concentrated in vacuo to provide a residue. This residue was taken up in methylene chloride and extracted with aqueous tartaric acid solution. The aqueous layer was basified with 1M sodium hydroxide solution and the product was extracted into methylene chloride. Evaporation of solvent in vacuo left an oily solid which, after thorough washing with a 1:2 mixture of toluene and hexane, afforded 0.60 g of (4R)-4-(di-n-propylamino) -1,3,4,5-tetrahydrobenz [cd]indole-6-carboxylic hydrazide.

후처리

  1. filtrationAfter filtering
  2. concentrationthe mixture was concentrated in vacuo
  3. customto provide a residue
  4. extractionextracted with aqueous tartaric acid solution
  5. extractionthe product was extracted into methylene chloride
  6. customEvaporation of solvent in vacuo
  7. waitleft an oily solid which
  8. washafter thorough washing with a 1:2 mixture of toluene and hexane

출처 및 근거

ORD 기록
ord-850ae2fc655b41c3bc97d99377e9a07b
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750554

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