Water → HCID 21833848, compound

HRID 1741108Notes

Reaction equation

HRID 1741108 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH:19]3[CH2:24][N:23]([CH3:25])[CH2:22][CH2:21][C:20]43[C:36]3[C:28](=[CH:29][C:30]5[CH2:31][CH2:32][NH:33][C:34]=5[CH:35]=3)[O:27][CH2:26]4)=[O:18])=[CH:13][CH:12]=2)=[C:7]([CH3:37])[CH:6]=1)=O.O.[NH2:39][NH2:40].O>CO>[NH:39]([C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH:19]3[CH2:24][N:23]([CH3:25])[CH2:22][CH2:21][C:20]43[C:36]3[C:28](=[CH:29][C:30]5[CH2:31][CH2:32][NH:33][C:34]=5[CH:35]=3)[O:27][CH2:26]4)=[O:18])=[CH:13][CH:12]=2)=[C:7]([CH3:37])[CH:6]=1)=[O:2])[NH2:40]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 21833716HCID 21833716, compound

Product 1

HCID 21833848HCID 21833848, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5'(4'-methoxycarbonyl-2'-methylbiphenyl-4-carbonyl)-1'-methyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (E22, 0.75 g, 1.5 mmole) in methanol (25 ml) was treated with hydrazine monohydrate (1.05 ml) and heated under reflux for 18 h. The reaction mixture was allowed to cool, then poured into water (50 ml) and the solid which precipitated out was filtered off and dried (0.61 g, 81%). A 50 mg portion was purified by preparative TLC on silica gel eluting with 20% methanol/chloroform to afford the title compound as a white solid mp. 130-135° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 h
  3. temperatureto cool
  4. customthe solid which precipitated out
  5. filtrationwas filtered off
  6. customdried (0.61 g, 81%)
  7. customA 50 mg portion was purified by preparative TLC on silica gel eluting with 20% methanol/chloroform

Sources & evidence

ORD record
ord-3a12074f423f4285b0d9d92c081b81fa
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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