1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 136138832, compound

HRID 2278567Notes

Reaction equation

HRID 2278567 reaction equation
N1(C2N=C(CC([O-])=O)NC(=O)C=2)CC[O:4]CC1.[Na+].Cl[C:20]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:21]=1[CH2:22][CH:23]([CH3:45])[N:24]2[C:29](=[O:44])[CH2:30][C:31]1[NH:36][C:35](=[O:37])[CH:34]=[C:33]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)[N:32]=1.Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1.CN(C)C=O>[OH:4][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:21]=1[CH2:22][CH:23]([CH3:45])[N:24]2[C:29](=[O:44])[CH2:30][C:31]1[NH:36][C:35](=[O:37])[CH:34]=[C:33]([N:38]2[CH2:43][CH2:42][O:41][CH2:40][CH2:39]2)[N:32]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetateHCID 136138826HCID 136138826, compound

Product 1

HCID 136138832HCID 136138832, compoundYield 107.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

The product is prepared by following the procedure described in example 1c using 1.2 g of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate, 0.82 g of 2-methyl-2,3-dihydro-1H-indol-4-ol [reference example 1c] and 1.17 g of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride in a mixture of 1.1 ml of pyridine and 25 ml of N,N-dimethylformamide. After purification of the residue by chromatography on a 90 g cartridge of 15-40 μm silica, elution being carried out with pure dichloromethane and then with 98/2 then 95/5 v/v dichloromethane/methanol mixtures at a flow rate of 80 ml/min, 0.84 g of 2-[2-(4-hydroxy-2-methyl-2,3-dihydro-1H-indol-1-yl)-2-oxoethyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one is obtained in the form of a very pale pink powder, the characteristics of which are the following:

Workup

  1. customThe product is prepared
  2. customAfter purification of the residue by chromatography
  3. washon a 90 g cartridge of 15-40 μm silica, elution

Sources & evidence

ORD record
ord-4a80c4c89bbb4145928df001918290b9
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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