Potassium tert-butoxide → HCID 66958543, compound

HRID 1364019Notes

Reaction equation

HRID 1364019 reaction equation
CC(C)([O-])C.[K+].[Si:7]([O:14][CH:15]([CH2:25][N:26]1[C:38]2[C:37]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[N:31]=[CH:30][C:29]=2[N:28]=[C:27]1[CH2:39]Cl)[CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]>O1CCCC1>[Si:7]([O:14][CH:15]1[CH2:25][N:26]2[C:38]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=[CH:30][C:29]=3[N:28]=[C:27]2[CH2:39][N:17]([C:18]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:24])[CH2:16]1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 66958143HCID 66958143, compound

Product 1

HCID 66958543HCID 66958543, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium tert-butoxide (116.1 mL of a 1M solution in tetrahydrofuran) was added to a solution of tert-butyl 2-{[tert-butyl(dimethyl)silyl]oxy}-3-[2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propylcarbamate (42.72 g, 84.57 mmol) in anhydrous tetrahydrofuran (THF) (50 mL), and the reaction was stirred overnight at ambient temperature and then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with dichloromethane:methanol in a gradient from 99:1 to 95:5) to provide 20.23 g of tert-butyl 11-{[tert-butyl(dimethyl)silyl]oxy}-11,12-dihydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(10H)-carboxylate.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude product was purified by column chromatography on silica gel (
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-1042805d96244be0965885ef75e759a8
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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