Ethyl orthopropionate → tert-butyl 4-[(7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate

HRID 9441

Reaction equation

HRID 9441 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)=[CH:9][CH:8]=[C:7]([Br:27])[CH:6]=2.[C:28](OCC)(OCC)(OCC)[CH2:29][CH3:30]>>[Br:27][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[N:12]([CH2:13][CH:14]4[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:16][CH2:15]4)[C:28]([CH2:29][CH3:30])=[N:1][C:2]=3[CH:3]=[N:4][C:5]=2[CH:6]=1

Participants

3

Reactant 2

HCID 66995Ethyl orthopropionateHCID 21984428Tert-butyl 4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]piperidine-1-carboxylate

Product 1

HCID 21984257tert-butyl 4-[(7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylateYield 77.1%

Procedure

The method described in Part A of Examples 142–144 was used to treat tert-butyl 4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]piperidine-1-carboxylate (15.0 g, 34.5 mmol) with triethyl orthopropionate (6.68 g, 37.9 mmol). After completion, the reaction mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (eluting with 95:5 chloroform:CMA) followed by recrystallization from ethyl acetate to provide 12.6 g of tert-butyl 4-[(7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate as a white powder, mp 208–209° C.

Workup

  1. concentrationAfter completion, the reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash column chromatography on silica gel (eluting with 95:5 chloroform:CMA)
  3. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-9ba31f07c1b444a68ce2aed691763f55
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Linked notes

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