Ethyl Acetate → HCID 66958550, compound

HRID 1364035Notes

Reaction equation

HRID 1364035 reaction equation
Cl[CH2:2][C:3]1[N:4]([CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=1.CC(C)([O-])C.[K+].C(OCC)(=O)C>C1COCC1>[CH:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[C:5]1[N:4]3[CH2:16][CH2:17][CH2:18][N:19]([C:20]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:26])[CH2:2][C:3]3=[N:15][C:6]=1[CH:7]=[N:8]2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 66958458HCID 66958458, compound

Product 1

HCID 66958550HCID 66958550, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A modification of the method described in Part D of Example 4 was used to treat tert-butyl 3-[2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propylcarbamate (36.76 g, 98.1 mmol) with potassium tert-butoxide (107.9 mL of a 1 M solution in THF). Following the work-up procedure, the product was mixed with ethyl acetate. The resulting mixture was filtered to remove a solid, and the filtrate was concentrated under reduced pressure to provide 30.0 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. filtrationThe resulting mixture was filtered
  2. customto remove a solid
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1a4b62bfb0224396be205db8701e3ccd
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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