Pyridine → 6-(morpholin-4-yl)-2-{2-oxo-2-[4-(1-propylpiperidin-3-yl)-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-one

HRID 2278617Notes

Reaction equation

HRID 2278617 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N:8]1[C:13](=[O:14])[CH:12]=[C:11]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:10]=[C:9]1[CH2:21][C:22](=[O:36])[N:23]1[C:31]2[C:26](=[C:27](C(F)(F)F)[CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24]1.Cl.CN(C)[CH2:40][CH2:41][CH2:42]N=C=NCC.N1(C2N=C(CC([O-])=O)NC(=O)C=2)CCOCC1.[Na+]>CN(C)C=O>[N:15]1([C:11]2[N:10]=[C:9]([CH2:21][C:22](=[O:36])[N:23]3[C:31]4[C:26](=[C:27]([CH:3]5[CH2:4][CH2:5][CH2:6][N:1]([CH2:40][CH2:41][CH3:42])[CH2:2]5)[CH:28]=[CH:29][CH:30]=4)[CH2:25][CH2:24]3)[NH:8][C:13](=[O:14])[CH:12]=2)[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 573895513-methyl-6-(morpholin-4-yl)-2-{2-oxo-2-[4-(trifluoromethyl)-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-oneHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 1360696076-(morpholin-4-yl)-2-{2-oxo-2-[4-(1-propylpiperidin-3-yl)-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.2 ml of pyridine, 25.7 mg of 4-(1-propylpiperidin-3-yl)-2,3-dihydro-1H-indole (reference example 4d) and 17.8 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are successively added to a solution of 20.5 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (example 1d, step 2d) in 0.8 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 24 hours, and then concentrated under reduced pressure. The residue is taken up in 10 ml of water and then extracted with dichloromethane (4×20 ml). The organic phases are combined and then washed with water and concentrated under reduced pressure. After oven-drying, 16.1 mg of 6-(morpholin-4-yl)-2-{2-oxo-2-[4-(1-propylpiperidin-3-yl)-2,3-dihydro-1H-indol-1-yl]ethyl}pyrimidin-4(3H)-one are obtained in the form of a pink solid, the characteristics of which are the following:

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with dichloromethane (4×20 ml)
  3. washwashed with water
  4. concentrationconcentrated under reduced pressure
  5. customAfter oven-drying

Sources & evidence

ORD record
ord-8d04c01b63fa452b91cc7a9647e1e84c
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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