Potassium tert-butoxide → HCID 66958550, compound

HRID 1364037Notes

Reaction equation

HRID 1364037 reaction equation
CC(C)([O-])C.[K+].Cl[CH2:8][C:9]1[N:10]([CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:21]=1>C1COCC1>[CH:19]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:20]=1[C:11]1[N:10]3[CH2:22][CH2:23][CH2:24][N:25]([C:26]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:32])[CH2:8][C:9]3=[N:21][C:12]=1[CH:13]=[N:14]2

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 66958458HCID 66958458, compound

Product 1

HCID 66958550HCID 66958550, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium tert-butoxide (77.2 mL of a 1 M solution in THF) was added to a solution of tert-butyl 3-[2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propylcarbamate (24.12 g, 64.34 mmol, prepared according to the methods described in Example 6 Parts A through C) in THF (250 mL), and the reaction was stirred overnight at ambient temperature. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluting with 2N ammonia in methanol/dichloromethane in a gradient from 0:100 to 15:85) to provide 9.1 g of tert-butyl 11,12-dihydro-8H-[1,4]diazepino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(10H)-carboxylate.

Workup

  1. customprepared
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (
  4. washeluting with 2N ammonia in methanol/dichloromethane in a gradient from 0:100 to 15:85)

Sources & evidence

ORD record
ord-02e7a68423e74d5da0a960417726c6dc
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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