Pyridine → HCID 136069606, compound

HRID 2278616Notes

Reaction equation

HRID 2278616 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.CN(C)[CH2:10][CH2:11][CH2:12]N=C=NCC.[N:19]1([C:25]2[N:26]=[C:27]([CH2:32][C:33]([O-:35])=O)[NH:28][C:29](=[O:31])[CH:30]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.[Na+].N1(C2N=C(CC(=O)N3[C:59]4[C:54](=[C:55]([O:60][C:61](F)(F)F)[CH:56]=[CH:57][CH:58]=4)CC3)NC(=O)C=2)CCOCC1>CN(C)C=O.C(OCC)(=O)C.O>[CH3:61][O:60][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][C:54]=1[C:10]1[CH:11]=[CH:12][CH:2]=[C:3]2[C:4]=1[CH2:5][CH2:6][N:1]2[C:33](=[O:35])[CH2:32][C:27]1[NH:28][C:29](=[O:31])[CH:30]=[C:25]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[N:26]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetateHCID 136069600HCID 136069600, compound

Product 1

HCID 136069606HCID 136069606, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.105 ml of pyridine and 165 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are successively added to a solution of 170 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (example 1d, step 2d) in 3 ml of N,N-dimethylformamide. After stirring at ambient temperature for 15 minutes, 140 mg of 4-(2-methoxyphenyl)-2,3-dihydro-1H-indole (reference example 3d) are added. The reaction mixture is stirred at ambient temperature for 16 hours, and then 20 ml of water and 3 ml of ethyl acetate are added. After stirring at ambient temperature for 1 hour, the precipitate formed is filtered off, and then rinsed successively with water and diethyl ether. After drying under reduced pressure at 40° C., 202 mg of 2-{2-[4-(2-methoxyphenyl)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-6-(morpholin-4-yl)pyrimidin-4(3H)-one are obtained in the form of a pale pink solid, the characteristics of which are the following:

Workup

  1. stirringThe reaction mixture is stirred at ambient temperature for 16 hours
  2. stirringAfter stirring at ambient temperature for 1 hour
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. washrinsed successively with water and diethyl ether
  6. customAfter drying under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-3387e96d4cc24722a2a6dbddb696ac47
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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