Acetone → 5-Cyano-1-[3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)indol-5-yl]-1H-benzimidazole

HRID 1419148Notes

Reaction equation

HRID 1419148 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[C:13]3[C:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH:20]=2)=[C:5]([N+:32]([O-])=O)[CH:4]=1)#[N:2].[CH2:35](OC=C(C#N)C#N)C.CC(C)=O>C(O)C.C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]2[N:9]([C:10]3[CH:11]=[C:12]4[C:16](=[CH:17][CH:18]=3)[NH:15][CH:14]=[C:13]4[C:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH:20]=3)[CH:35]=[N:32][C:5]=2[CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 180AcetoneHCID 671522-(Ethoxymethylene)propanedinitrileHCID 538656485-(4-Cyano-2-nitrophenyl)amino-3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-1H-indole

Product 1

HCID 542383575-Cyano-1-[3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)indol-5-yl]-1H-benzimidazoleYield 10%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

5-(4-Cyano-2-nitrophenyl)amino-3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-1H-indole was used. Reduction was by aqueous FeSO4 in ethanol, the cyclization reaction used ethoxymethylene malononitrile, and the cyclization reaction was heated for 56 hours. Chromatography using 5% acetone in methylene chloride afforded the title compound (10%) as a brown foam: Rf =0.5 in 5% acetone in methylene chloride; HRMS calculated for C26H25N5O2 439.2011, found 439.1999.

Workup

  1. customthe cyclization reaction
  2. customthe cyclization reaction
  3. temperaturewas heated for 56 hours

Sources & evidence

ORD record
ord-f37f864d6e5d4083845d628c313d5b37
Source dataset
uspto-grants-1999_03
Patent number
US05886008

Reaction notes

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