Dimethylamine → HCID 59563517, compound

HRID 2090257Notes

Reaction equation

HRID 2090257 reaction equation
[CH3:1][NH:2][CH3:3].[NH2:4][C:5]1[C:14]2[N:15]=[C:16]([CH2:38][CH2:39][CH2:40][CH3:41])[N:17]([CH2:18][CH2:19][CH2:20][N:21]([CH2:26][C:27]3[CH:28]=[C:29]([CH2:33][C:34]([O:36][CH3:37])=[O:35])[CH:30]=[CH:31][CH:32]=3)[CH2:22][CH2:23][CH2:24]Cl)[C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]=1.[I-].[Na+]>C1COCC1.CN(C=O)C>[NH2:4][C:5]1[C:14]2[N:15]=[C:16]([CH2:38][CH2:39][CH2:40][CH3:41])[N:17]([CH2:18][CH2:19][CH2:20][N:21]([CH2:26][C:27]3[CH:28]=[C:29]([CH2:33][C:34]([O:36][CH3:37])=[O:35])[CH:30]=[CH:31][CH:32]=3)[CH2:22][CH2:23][CH2:24][N:2]([CH3:3])[CH3:1])[C:13]=2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:6]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 5238Sodium IodideHCID 68430884Methyl 2-(3-(((3-(4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)propyl)(3-chloropropyl)amino)methyl)phenyl)acetate

Product 1

HCID 59563517HCID 59563517, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A solution of dimethylamine in THF (2M, 6 mL) was added to a mixture of the product from step (ix) (1.17 mmol) and sodium iodide (250 mg) in DMF (5 mL) at rt. The mixture was heated at 55° C. in a sealed vessel for 24 h, cooled, filtered and the filtrate purifed by RPHPLC. The fractions containing the desired compound were evaporated to dryness and the residue triturated with ether/isohexane, 270 mg.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. additionThe fractions containing the desired compound
  4. customwere evaporated to dryness
  5. customthe residue triturated with ether/isohexane, 270 mg

Sources & evidence

ORD record
ord-fe3fa2379f044658bc5d5fce914054f3
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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