1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 136378693, compound

HRID 2278637Notes

Reaction equation

HRID 2278637 reaction equation
N1(C2N=[C:9]([CH2:14][C:15]([O-])=O)NC(=O)C=2)CCOCC1.[Na+].[N:19]1([C:25]2[N:30]=[C:29]([CH2:31][C:32](=[O:48])[N:33]3[C:41]4[C:36](=[C:37](C5C=CC=CN=5)[CH:38]=[CH:39][CH:40]=4)[CH2:35][CH2:34]3)[NH:28][C:27](=[O:49])[CH:26]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1.CN(C)C=O>[CH:14]1([CH:34]2[CH2:35][C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:33]2[C:32](=[O:48])[CH2:31][C:29]2[NH:28][C:27](=[O:49])[CH:26]=[C:25]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[N:30]=2)[CH2:15][CH2:9]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 136069610HCID 136069610, compound

Product 1

HCID 136378693HCID 136378693, compoundYield 160.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

(±)-2-[2-(2-Cyclopropyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one is prepared by following the procedure described in example 1 using 0.90 g of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate, 0.60 g of (±)-2-cyclopropylindoline (reference example 12d) and 0.86 g of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride in a mixture of 0.56 ml of pyridine and 10 ml of N,N-dimethylformamide. After purification by chromatography on a 100 g column of 20-45 μm silica, elution being carried out with a 90/10 v/v dichloromethane/methanol mixture, 0.88 g of (±)-2-[2-(2-cyclopropyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one is obtained in the form of a cream foam, the characteristics of which are the following:

Workup

  1. custom(±)-2-[2-(2-Cyclopropyl-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 100 g column of 20-45 μm silica, elution

Sources & evidence

ORD record
ord-457b04ab2bd5467ebb00779b0bc7c760
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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