1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 136098496, compound

HRID 2278554Notes

Reaction equation

HRID 2278554 reaction equation
[Na].[CH3:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]2[N:10]=[C:11]([CH2:16][C:17]([OH:19])=O)[NH:12][C:13](=[O:15])[CH:14]=2)[CH2:4]1.[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:22]=1[CH2:23][CH2:24][NH:25]2.Cl.CN(C)CCCN=C=NCC>O.CN(C=O)C.N1C=CC=CC=1>[Cl:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:22]=1[CH2:23][CH2:24][N:25]2[C:17](=[O:19])[CH2:16][C:11]1[NH:12][C:13](=[O:15])[CH:14]=[C:9]([N:5]2[CH2:6][CH2:7][O:8][CH:3]([CH3:2])[CH2:4]2)[N:10]=1

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 30163064-ChloroindolineHCID 5360545SodiumHCID 136378672HCID 136378672, compound

Product 1

HCID 136098496HCID 136098496, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

0.975 g of the sodium salt of [4-(2-methylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid (example 1b, step 2b), 0.534 g of 4-chloroindoline, 0.57 ml of pyridine and 15 ml of DMF are placed in a round-bottomed flask, and then 0.9 g of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride is added. The reaction mixture is stirred at ambient temperature for 72 hours. The reaction mixture is poured into 50 ml of water, with stirring, and then the solid formed is filtered off through sintered glass and washed 3 times with approximately 15 ml of water, washed with 10 ml of EtOAc and rinsed with twice approximately 5 ml of diisopropyl ether, and the resulting product is left to air-dry under a hood. 2-[2-(4-Chloro-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2-methylmorpholin-4-yl)-3H-pyrimidin-4-one is isolated (0.98 g) and characterized in the form of an off-white solid (yield 71%).

Workup

  1. stirringwith stirring
  2. customthe solid formed
  3. filtrationis filtered off through sintered glass
  4. washwashed 3 times with approximately 15 ml of water
  5. washwashed with 10 ml of EtOAc
  6. washrinsed with twice approximately 5 ml of diisopropyl ether
  7. waitthe resulting product is left
  8. customto air-dry under a hood

Sources & evidence

ORD record
ord-f2deabe5b8694004883ce234c06ed041
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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