Diethyl Ether → HCID 58967516, compound

HRID 909345Notes

Reaction equation

HRID 909345 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:25][CH2:26][CH2:27][O:28][CH:29]([CH3:31])[CH3:30])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:12][C:11]=3[N+:10]([O-])=[CH:9][C:8]=2[N:24]=1)[CH3:2].[OH-].[NH4+:33].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(OCC)C>ClCCl>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:25][CH2:26][CH2:27][O:28][CH:29]([CH3:31])[CH3:30])[C:7]2[C:16]3[CH:15]=[CH:14][C:13]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[CH:12][C:11]=3[N:10]=[C:9]([NH2:33])[C:8]=2[N:24]=1)[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 67382408HCID 67382408, compound

Product 1

HCID 58967516HCID 58967516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Ethoxymethyl-1-(3-isopropoxypropyl)-7-(morpholin-4-yl)-1H-imidazo[4,5-c]quinoline 5-oxide from Part B was dissolved in dichloromethane (4 mL). Ammonium hydroxide (2 mL) was added, followed by p-toluenesulfonyl chloride (0.074 g). The reaction was stirred for 24 hours. The layers were separated and the aqueous fraction was extracted with dichloromethane. The combined organic fractions were concentrated under reduced pressure to yield a yellow-brown oil. The oil was covered with diethyl ether and a precipitate formed. The solid was recovered by filtration and then dried to provide 0.085 g of 2-ethoxymethyl-1-(3-isopropoxypropyl)-7-(morpholin-4-yl)-1H-imidazo[4,5-c]quinolin-4-amine as a white powder, mp 161-162.5° C.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous fraction was extracted with dichloromethane
  3. concentrationThe combined organic fractions were concentrated under reduced pressure
  4. customto yield a yellow-brown oil
  5. customa precipitate formed
  6. filtrationThe solid was recovered by filtration
  7. customdried

Sources & evidence

ORD record
ord-7391a342ae564123bd53ca414e3c00b3
Source dataset
uspto-grants-2011_09
Patent number
US08017779B2

Reaction notes

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