2-Phenyl-2,3-dihydro-1H-indole → HCID 136378691, compound

HRID 2278632Notes

Reaction equation

HRID 2278632 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+].[C:19]1([CH:25]2[CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[NH:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl.CN(C)CCCN=C=NCC>N1C=CC=CC=1.CN(C)C=O>[N:1]1([C:7]2[N:8]=[C:9]([CH2:14][C:15](=[O:17])[N:26]3[C:27]4[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:33][CH:25]3[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[NH:10][C:11](=[O:13])[CH:12]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 1177592-Phenyl-2,3-dihydro-1H-indoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136378691HCID 136378691, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

(±)-6-(Morpholin-4-yl)-2-{2-oxo-2-[2-phenyl-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-one is prepared by following the procedure described in example 1d, step 3d, using 0.50 g of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate, 0.42 g of 2-phenylindoline (which can be prepared according to Santangelo, E. M. et al. Eur. J. Org. Chem. 2008, 5915), and 0.48 g of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride in a mixture of 0.31 ml of pyridine and 10 ml of N,N-dimethylformamide. After purification by chromatography on a 50 g column of 20-45 μm silica, elution being carried out with a 90/10 v/v dichloromethane/methanol mixture, 0.43 g of (±)-6-(morpholin-4-yl)-2-{2-oxo-2-[2-phenyl-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-one is obtained in the form of a cream-colored solid, the characteristics of which are the following:

Workup

  1. custom(±)-6-(Morpholin-4-yl)-2-{2-oxo-2-[2-phenyl-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-one is prepared
  2. customAfter purification by chromatography
  3. washon a 50 g column of 20-45 μm silica, elution

Sources & evidence

ORD record
ord-ebc5c6d902c64e519f4feeeb32944bd0
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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