Pyridine → HCID 136196449, compound

HRID 2278633Notes

Reaction equation

HRID 2278633 reaction equation
[N:1]1C=CC=C[CH:2]=1.[N:7]1([C:13]2[N:18]=[C:17]([CH2:19][C:20](=[O:36])[N:21]3[C:29]4[C:24](=[C:25](C5C=CN=CC=5)[CH:26]=[CH:27][CH:28]=4)[CH2:23][CH2:22]3)[NH:16][C:15](=[O:37])[CH:14]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.Cl.[CH3:39][N:40]([CH3:49])[CH2:41][CH2:42]CN=C=NCC.N1(C2N=C(CC([O-])=O)NC(=O)C=2)CCOCC1.[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[CH3:49][N:40]1[CH2:39][CH2:2][N:1]([C:25]2[CH:26]=[CH:27][CH:28]=[C:29]3[C:24]=2[CH2:23][CH2:22][N:21]3[C:20](=[O:36])[CH2:19][C:17]2[NH:16][C:15](=[O:37])[CH:14]=[C:13]([N:7]3[CH2:8][CH2:9][O:10][CH2:11][CH2:12]3)[N:18]=2)[CH2:42][CH2:41]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 136069609HCID 136069609, compound

Product 1

HCID 136196449HCID 136196449, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

8 ml of pyridine, 160 mg of 4-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-indole (reference example 10d) and 212 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are successively added to a solution of 288 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (example 1d, step 2d) in 8 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 48 hours. After the addition of 50 ml of water and extraction with ethyl acetate, the organic phases are combined and then dried over magnesium sulfate, filtered through sintered glass, and concentrated under reduced pressure. After purification of the residue by silica column chromatography, elution being carried out with a mixture of dichloromethane and 7N ammoniacal methanol (90/10), 29 mg of 2-{2-[4-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-6-(morpholin-4-yl)pyrimidin-4(3H)-one are obtained in the form of a white-pink powder, the characteristics of which are the following:

Workup

  1. dry with materialdried over magnesium sulfate
  2. filtrationfiltered through sintered glass
  3. concentrationconcentrated under reduced pressure
  4. customAfter purification of the residue
  5. washby silica column chromatography, elution
  6. additionbeing carried out with a mixture of dichloromethane and 7N ammoniacal methanol (90/10), 29 mg of 2-{2-[4-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-6-(morpholin-4-yl)pyrimidin-4(3H)-one
  7. customare obtained in the form of a white-pink powder

Sources & evidence

ORD record
ord-90c8bbadbb354762bbf975024f2710c9
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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