1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 136378689, compound

HRID 2278587Notes

Reaction equation

HRID 2278587 reaction equation
[N:1]1([C:7]2[N:8]=[C:9]([CH2:14][C:15]([O-:17])=O)[NH:10][C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Na+].[CH2:19]([CH:21]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22]1)[CH3:20].Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1.CN(C)C=O>[CH2:19]([CH:21]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]1[C:15](=[O:17])[CH2:14][C:9]1[NH:10][C:11](=[O:13])[CH:12]=[C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)[N:8]=1)[CH3:20]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 107731212-ethyl-2,3-dihydro-1H-indoleHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136378689HCID 136378689, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

(±)-2-[2-(2-Ethyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one is prepared by following the procedure described in example 1c using 0.40 g of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate, 0.25 g of 2-ethylindoline [which can be prepared according to patent WO2009065920] and 0.39 g of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride in a mixture of 250 ml of pyridine and 6.5 ml of N,N-dimethylformamide. After purification by chromatography on a 25 g cartridge of 15-40 μm silica, elution being carried out successively with 99/1 then 98/2 and 97/3 v/v dichloromethane/methanol mixtures, at a flow rate of 30 ml/min, 0.35 g of (±)-2-[2-(2-ethyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one is obtained in the form of a white foam, the characteristics of which are the following:

Workup

  1. custom(±)-2-[2-(2-Ethyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one is prepared
  2. customAfter purification by chromatography
  3. washon a 25 g cartridge of 15-40 μm silica, elution

Sources & evidence

ORD record
ord-b02b8d74e7ae4ddc96e7432ad3d81f88
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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