4-Toluenesulfonyl chloride → 2-(Ethoxymethyl)-1-propyl-8-(tetrahydrofuran-3-yloxy)-1H-imidazo[4,5-c]quinolinamine

HRID 540910

Reaction equation

HRID 540910 reaction equation
C(OCC1[N:6](CCC)C2C3C=C(O)C=CC=3N=CC=2N=1)C.[CH2:22]([O:24][CH2:25][C:26]1[N:27]([CH2:45][CH2:46][CH3:47])[C:28]2[C:37]3[CH:36]=[C:35]([O:38][CH:39]4[CH2:43][CH2:42][O:41][CH2:40]4)[CH:34]=[CH:33][C:32]=3[N:31]=[CH:30][C:29]=2[N:44]=1)[CH3:23].OC1CCOC1.OCCCN1CCCC1=O.C(OCC1N(CCC)C2C3C=C(OC4CCOC4)C=CC=3N=C(N)C=2N=1)C.[OH-].[NH4+].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>>[CH2:22]([O:24][CH2:25][C:26]1([NH2:6])[NH:44][C:29]2[CH:30]=[N:31][C:32]3[CH:33]=[CH:34][C:35]([O:38][CH:39]4[CH2:43][CH2:42][O:41][CH2:40]4)=[CH:36][C:37]=3[C:28]=2[N:27]1[CH2:45][CH2:46][CH3:47])[CH3:23]

Participants

8

Reactant 7

HCID 73974-Toluenesulfonyl chlorideHCID 99603-Furanol, tetrahydro-HCID 14923Ammonium HydroxideHCID 5667441-(3-Hydroxypropyl)pyrrolidin-2-oneHCID 588337072-(ethoxymethyl)-1-propyl-8-(tetrahydrofuran-3-yloxy)-1H-imidazo[4,5-c]quinolin-4-amineHCID 670510882-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-ol2×HCID 689693812-(ethoxymethyl)-1-propyl-8-(tetrahydrofuran-3-yloxy)-1H-imidazo[4,5-c]quinoline2×

Product 1

HCID 695070192-(Ethoxymethyl)-1-propyl-8-(tetrahydrofuran-3-yloxy)-1H-imidazo[4,5-c]quinolinamine

Procedure

The synthesis of 2-(ethoxymethyl)-1-propyl-1H-imidazo[4,5-c]quinolin-8-ol is described in Parts A-I of Example 2. A modification of the method described in Part A of Example 405 was used to convert 2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-ol into 2-(ethoxymethyl)-1-propyl-8-(tetrahydrofuran-3-yloxy)-1H-imidazo[4,5-c]quinoline using 3-hydroxytetrahydrofuran in lieu of 1-(3-hydroxypropyl)pyrrolidin-2-one. Modifications of the methods described in Parts B and C of Example 405 were used to convert 2-(ethoxymethyl)-1-propyl-8-(tetrahydrofuran-3-yloxy)-1H-imidazo[4,5-c]quinoline into 2-(ethoxymethyl)-1-propyl-8-(tetrahydrofuran-3-yloxy)-1H-imidazo[4,5-c]quinolin-4-amine. Parts B and C were combined by omitting the aqueous work up of Part B, in other words, the ammonium hydroxide and p-toluenesulfonyl chloride reagents used in Part C were added to the reaction mixture in Part B. The reaction was worked up as described in Part C of Example 405. 2-(Ethoxymethyl)-1-propyl-8-(tetrahydrofuran-3-yloxy)-1H-imidazo[4,5-c]quinolinamine was isolated as tan needles, mp 173-175° C.

Workup

  1. additionwere added to the reaction mixture in Part B

Sources & evidence

ORD record
ord-d17847d026d645e0a37aadc57e04656b
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Linked notes

Loading…