Benzaldehyde → HCID 67519559, compound

HRID 81930Notes

Reaction equation

HRID 81930 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=C(C=O)C=1.[NH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[C:34]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=[C:26]([NH2:35])[C:25]=2[N:24]=[C:23]1[CH2:36][O:37][CH2:38][CH3:39].NCCCCN1C2C3C=CC=CC=3N=C(N)C=2N=C1COC.FC(F)(F)C([O-])=O>>[CH2:1]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[C:34]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[N:27]=[C:26]([NH2:35])[C:25]=2[N:24]=[C:23]1[CH2:36][O:37][CH2:38][CH3:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 240BenzaldehydeHCID 103713-PyridinecarboxaldehydeHCID 84468TrifluoroacetateHCID 187839531-(4-aminobutyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amineHCID 67519397HCID 67519397, compound

Product 1

HCID 67519559HCID 67519559, compound

Procedure

The compounds in the table below were prepared and purified according to the methods of Parts B and C of Examples 467-478 using 1-(4-benzylaminobutyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine in lieu of 2-methoxymethyl-1-{4-[(pyridin-3-ylmethyl)amino]butyl}-1H-imidazo[4,5-c]quinolin-4-amine. 1-(4-Benzylaminobutyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine was prepared according to the general method of Part A of Examples 467-478 using benzaldehyde in lieu of pyridine 3-carboxaldehyde and 1-(4-aminobutyl)-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine in lieu of 1-(4-aminobutyl)-2-methoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine. The table below shows the reagent used for each example, the structure of the resulting compound, and the observed accurate mass for the isolated trifluoroacetate salt.

Workup

  1. customThe compounds in the table below were prepared
  2. custompurified

Sources & evidence

ORD record
ord-79e4ec8e96b44d3a8d14f6b4c45e30e4
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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