Isopropyl isocyanate → HCID 58833708, compound

HRID 540915Notes

Reaction equation

HRID 540915 reaction equation
[CH:1]([N:4]=[C:5]=[O:6])([CH3:3])[CH3:2].[CH2:7]([O:9][CH2:10][C:11]1[N:12]([CH2:32][CH2:33][CH3:34])[C:13]2[C:22]3[CH:21]=[C:20]([O:23][CH:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)[CH:19]=[CH:18][C:17]=3[N:16]=[C:15]([NH2:30])[C:14]=2[N:31]=1)[CH3:8]>ClCCl>[NH2:30][C:15]1[C:14]2[N:31]=[C:11]([CH2:10][O:9][CH2:7][CH3:8])[N:12]([CH2:32][CH2:33][CH3:34])[C:13]=2[C:22]2[CH:21]=[C:20]([O:23][CH:24]3[CH2:25][CH2:26][N:27]([C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:28][CH2:29]3)[CH:19]=[CH:18][C:17]=2[N:16]=1

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 58833720HCID 58833720, compound

Product 1

HCID 58833708HCID 58833708, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Isopropyl isocyanate (0.190 mL, 1.90 mmol) was added dropwise to a solution of 2-(ethoxymethyl)-8-(piperidin-4-yloxy)-1-propyl-1H-imidazo[4,5-c]quinolin-4-amine (prepared as described in Example 411, 0.730 g, 1.90 mmol) in dichloromethane (15 mL) at room temperature. The reaction was diluted with dichloromethane and stirred vigorously. A precipitate formed that was isolated by filtration to afford 0.743 g of 4-{[4-amino-2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl]oxy}-N-isopropylpiperidine-1-carboxamide as a white solid, mp 236.5-239° C.

Workup

  1. customA precipitate formed
  2. customthat was isolated by filtration

Sources & evidence

ORD record
ord-ee39501b16da431294411febd936acd3
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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