Potassium tert-butoxide → HCID 66958691, compound

HRID 1364067Notes

Reaction equation

HRID 1364067 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]2[C:19]3[N:27]([CH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:26]([CH2:39]Cl)=[N:25][C:20]=3[CH:21]=[N:22][C:23]=2[CH:24]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([O:14][C:15]1[CH:24]=[C:23]2[C:18]([C:19]3[N:27]4[CH2:28][CH2:29][CH2:30][N:31]([C:32]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:38])[CH2:39][C:26]4=[N:25][C:20]=3[CH:21]=[N:22]2)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxide2×HCID 66958171HCID 66958171, compound

Product 1

HCID 66958691HCID 66958691, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Under a nitrogen atmosphere, potassium tert-butoxide (142.7 mL of a 1 M solution in THF) was added to a solution of tert-butyl 3-[7-benzyloxy-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propylcarbamate (57.2 g, 118.9 mmol) in THF (142.7 mL). After the reaction was stirred at ambient temperature for ten minutes, additional potassium tert-butoxide (32 mL of a 1 M solution in THF) was added. The reaction was stirred overnight at ambient temperature and concentrated under reduced pressure. The crude reaction mixture was purified by column chromatography on silica gel (eluting with 2 N ammonia in methanol/chloroform in a 67-minute gradient from 0:100 to 3:97) and recrystallized sequentially from dichloromethane and acetonitrile to provide 26.99 g of tert-butyl 3-benzyloxy-11,12-dihydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(10H)-carboxylate.

Workup

  1. stirringThe reaction was stirred overnight at ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe crude reaction mixture
  4. customwas purified by column chromatography on silica gel (
  5. washeluting with 2 N ammonia in methanol/chloroform in a 67-minute gradient from 0:100 to 3:97) and
  6. customrecrystallized sequentially from dichloromethane and acetonitrile

Sources & evidence

ORD record
ord-d83a8935273947b49bb0382144a6381a
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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