tert-butyl N-(3-iodopropyl)carbamate → tert-butyl 3-{[1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}propylcarbamate

HRID 540822Notes

Reaction equation

HRID 540822 reaction equation
[CH3:1][CH:2]([CH3:21])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][C:12]([OH:17])=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[C:5]1[CH2:18][CH2:19][CH3:20].I[CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30]>O>[CH3:1][CH:2]([CH3:21])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][C:12]([O:17][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[C:5]1[CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 11231463tert-butyl N-(3-iodopropyl)carbamateHCID 1363405361-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-ol

Product 1

HCID 68969654tert-butyl 3-{[1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}propylcarbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A modification of the general method described in Part L of Example 2 was used to treat 1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-ol with tert-butyl 3-iodopropylcarbamate. The reaction mixture was diluted with water; a precipitate formed. The precipitate was isolated by filtration, washed with water and then with diethyl ether until the filtrate was clear, and dried overnight in a vacuum oven at 60° C. to yield tert-butyl 3-{[1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-7-yl]oxy}propylcarbamate as a tan powder.

Workup

  1. customa precipitate formed
  2. customThe precipitate was isolated by filtration
  3. washwashed with water
  4. customdried overnight in a vacuum oven at 60° C.

Sources & evidence

ORD record
ord-68590609b98941a5b2f3555bb00dc6f3
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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