(4R)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole-6carboxylic hydrazide → (-)(4R)-6-(5-phenyl-1,3,4-oxadiazol-2yl)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole

HRID 1377815Notes

Reaction equation

HRID 1377815 reaction equation
[CH2:1]([N:4]([CH2:21][CH2:22][CH3:23])[C@H:5]1[CH2:20][C:9]2=[CH:10][NH:11][C:12]3=[CH:13][CH:14]=[C:15]([C:16]([NH:18][NH2:19])=[O:17])[C:7](=[C:8]23)[CH2:6]1)[CH2:2][CH3:3]>COC(OC)(OC)C1C=CC=CC=1.C(Cl)Cl>[C:7]1([C:15]2[O:17][C:16]([C:15]3[CH:14]=[CH:13][C:12]4[NH:11][CH:10]=[C:9]5[CH2:20][C@H:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:21][CH2:22][CH3:23])[CH2:6][C:7]=3[C:8]=45)=[N:18][N:19]=2)[CH:8]=[CH:9][CH:20]=[CH:5][CH:6]=1

Participants

4

Reactant 1

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

Product 1

HCID 22868970(-)(4R)-6-(5-phenyl-1,3,4-oxadiazol-2yl)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indoleYield 163.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 69720Trimethyl orthobeznoateSolvent

Procedure

A solution of 0.20 g (0.64 mmol) of (4R)-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[cd]indole-6-carboxylic hydrazide in 2.0 ml of trimethylorthobenzoate was heated at 135° C. under nitrogen for 5 hours. After cooling, the semisolid mixture was dissolved in methylene chloride and the product was extracted into aqueous tartaric acid. The aqueous solution was basified with sodium carbonate and the product was extracted into methylene chloride. Evaporation of the methylene chloride left crystalline product which was then chromatographed over 3 g of silica gel using ethyl acetate as eluent. The product from the column was recrystallized from toluene to give 0.21 g of title compound.

Workup

  1. temperatureAfter cooling
  2. extractionthe product was extracted into aqueous tartaric acid
  3. extractionthe product was extracted into methylene chloride
  4. customEvaporation of the methylene chloride
  5. waitleft crystalline product which
  6. customwas then chromatographed over 3 g of silica gel
  7. customThe product from the column was recrystallized from toluene

Sources & evidence

ORD record
ord-65456e9e228f4df6bc3465181e9399fd
Source dataset
uspto-grants-1997_09
Patent number
US05665758

Reaction notes

Loading…