Benzaldehyde → HCID 67519559, compound

HRID 1925477Notes

Reaction equation

HRID 1925477 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 246-257 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 246-257 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-670d22e7650d45b1b1dcbbc30fc2da3a
Source dataset
uspto-grants-2012_05
Patent number
US08178677B2

Reaction notes

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