[1-(4-chloro-benzyl)-1H-indol-3-yl]-[4-pyridin-2-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-methanone → HCID 178519950, compound

HRID 1793610Notes

Reaction equation

HRID 1793610 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]([C:18]3[N:19](COCC[Si](C)(C)C)[CH:20]=[C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[N:22]=3)=[O:17])=[CH:8]2)=[CH:4][CH:3]=1>C(O)C.Cl>[Cl:1][C:2]1[CH:38]=[CH:37][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]([C:18]3[NH:19][CH:20]=[C:21]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[N:22]=3)=[O:17])=[CH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 12146869[1-(4-chloro-benzyl)-1H-indol-3-yl]-[4-pyridin-2-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-methanone

Product 1

HCID 178519950HCID 178519950, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of [1-(4-Chloro-benzyl)-1H-indol-3-yl]-[4-pyridin-2-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-methanone (10 mg, 18.4 mmol) in ethanol (3 mL) was added 5 drops of concentrated HCl. The resultant solution was heated to 70° C. for 10 hours. Volatile components were then removed under reduced pressure. Pure product [1-(4-Chloro-benzyl)-1H-indol-3-yl]-(4-pyridin-2-yl-1H-imidazol-2-yl)-methanonone was precipitated out from diethyl ether (7 mg, 92%). 1H NMR (CD3OD/THF-d8): 5.7 (s, 2H), 7.2–7.5 (m, 7H), 7.9 (s, 1H), 8.45–8.65 (m, 2H), 8.85 (br, 1H), 9.85 (br, 1H). ESMS calcd for (C24H17ClN4O): 412.1; found: 413.1 (M+H)+.

Workup

  1. customVolatile components were then removed under reduced pressure
  2. customPure product [1-(4-Chloro-benzyl)-1H-indol-3-yl]-(4-pyridin-2-yl-1H-imidazol-2-yl)-methanonone was precipitated out from diethyl ether (7 mg, 92%)

Sources & evidence

ORD record
ord-d42d62dfba464ca38ebb2a68e6f7aad6
Source dataset
uspto-grants-2006_07
Patent number
US07081466B2

Reaction notes

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