N,N-Dimethyl-1,3-propanediamine → HCID 10210345, compound

HRID 2179919Notes

Reaction equation

HRID 2179919 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]([CH3:43])[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20]3[N:25]=[C:24]([NH:26][C:27]4[CH:28]=[C:29]5[C:34](=[CH:35][CH:36]=4)[N:33]=[C:32]([CH3:37])[CH:31]=[C:30]5[N:38]([CH3:40])[CH3:39])[N:23]=[C:22](Cl)[N:21]=3)[CH:17]=2)[N:12]=[C:11]([CH3:42])[CH:10]=1.[CH3:44][N:45]([CH3:50])[CH2:46][CH2:47][CH2:48][NH2:49]>CN(C=O)C>[CH3:7][N:8]([CH3:43])[C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20]3[N:25]=[C:24]([NH:26][C:27]4[CH:28]=[C:29]5[C:34](=[CH:35][CH:36]=4)[N:33]=[C:32]([CH3:37])[CH:31]=[C:30]5[N:38]([CH3:40])[CH3:39])[N:23]=[C:22]([NH:49][CH2:48][CH2:47][CH2:46][N:45]([CH3:50])[CH3:44])[N:21]=3)[CH:17]=2)[N:12]=[C:11]([CH3:42])[CH:10]=1

Participants

5

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 11430Potassium CarbonateHCID 76327731HCID 76327731, compound

Product 1

HCID 10210345HCID 10210345, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

0.5 g (0.0036 mol) of potassium carbonate, 1 g (0.00189 mol) of 2,4-bis(4-dimethylamino-2-methylquinolin-6-yl)amino-6-chloro-[1,3,5]triazine prepared according to patent W0001561 and 1 ml (0.0078 mol) of N,N-dimethyl-1,3-propanediamine are successively loaded into a 250 ml round-bottomed flask containing 50 ml of DMF, with stirring, and then the mixture is heated for 15 hours at 100° C. The reaction medium is concentrated and taken up in 100 ml of water. The precipitate formed is filtered, washed with 2×50 ml of 0.1N NaOH and then dried. There are thus obtained 1.2 g of N,N′-bis(4-dimethylamino-2-methylquinolin-6-yl)-N″-(3-dimethylaminopropyl)-[1,3,5]triazine, which is purified by flash chromatography on 30 g of silica (35-70 μm), eluting with a mixture (85/10/5) of dichloromethane, methanol and triethylamine. There is thus obtained, after drying under vacuum at 40° C., 0.45 g (41%) of 2,4-bis(4-dimethylamino-2-methylquinolin-6-yl)amino-6-(3-dimethylaminopropyl)-amino-[1,3,5]triazine, in the form of a yellow powder whose characteristics are the following:

Workup

  1. customare successively loaded into a 250 ml round-bottomed flask
  2. concentrationThe reaction medium is concentrated
  3. customThe precipitate formed
  4. filtrationis filtered
  5. washwashed with 2×50 ml of 0.1N NaOH
  6. customdried
  7. customis purified by flash chromatography on 30 g of silica (35-70 μm)
  8. washeluting with a mixture (85/10/5) of dichloromethane, methanol and triethylamine
  9. customThere is thus obtained
  10. customafter drying under vacuum at 40° C.

Sources & evidence

ORD record
ord-04b44672380b4ed1b04d199a04a8c117
Source dataset
uspto-grants-2005_05
Patent number
US06887873B2

Reaction notes

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