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

HRID 1419152Notes

Reaction equation

HRID 1419152 reaction equation
[C:1]([C:3]1[CH:33]=[CH:32][C:6]2[N:7]([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(OC(C)(C)C)=O)[CH2:21][CH:20]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1)#[N:2]>C(Cl)Cl>[C:1]([C:3]1[CH:33]=[CH:32][C:6]2[N:7]([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][NH:22][CH2:21][CH:20]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1)#[N:2]

Participants

3

Reactant 1

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

Product 1

HCID 443171785-Cyano-1-[3-(1,2,5,6-tetrahydropyrid-4-yl)indol-5-yl]-1H-benzimidazoleYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Cyano-1-[3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)indol-5-yl]-1H-benzimidazole was used, and methylene chloride was used as solvent. Filtration afforded the title compound (75%) as a yellow solid: mp, decomposes at 240° C.; IR (KBr) 2228 cm-1 ; 13C NMR (CD3OD) δ 144.4, 137.9, 133.6, 131.1, 129.9, 126.0, 125.3, 125.2, 120.1, 118.4, 118.3, 117.5, 117.3, 116.1, 114.8, 113.2, 112.9, 110.4, 66.7, 42.0, 40.9. Anal. calcd. for C21H17N5.1.1 C4H8O2 [dioxane].1.1 HCl: C, 64.03; H, 5.69; N, 14.70. Found: C, 64.20; H, 5.54; N, 14.47.

Workup

  1. filtrationFiltration

Sources & evidence

ORD record
ord-c8ae1feaaaa64e2bbf1d9501f7fb90b1
Source dataset
uspto-grants-1999_03
Patent number
US05886008

Reaction notes

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