(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 263527Notes

Reaction equation

HRID 263527 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 trimethyl-orthobenzoate 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-dcef09b90438454391c73b0e967ed39e
Source dataset
uspto-grants-1997_07
Patent number
US05643930

Reaction notes

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