Pyridine → HCID 136138826, compound

HRID 2278562Notes

Reaction equation

HRID 2278562 reaction equation
[ClH:1].CN(C)[CH2:4][CH2:5][CH2:6]N=C=NCC.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[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+].[CH3:37]N(C)C=O>>[Cl:1][C:4]1[CH:5]=[CH:6][CH:37]=[C:18]2[C:17]=1[CH2:16][CH:15]([CH3:14])[N:13]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

5

Reactant 4

HCID 1049PyridineHCID 6228Dimethylformamide2×HCID 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 136138826HCID 136138826, compound

Procedure

549 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 350 μl of pyridine are added to a solution of 564 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate in 5 ml of N,N-dimethylformamide. The resulting suspension is stirred at ambient temperature for 10 minutes, and then a solution of 398 mg of 4-chloro-2-methyl-2,3-dihydro-1H-indoline [which can be prepared according to U.S. Pat. No. 4,416,884 (1983)] in 9 ml of N,N-dimethylformamide is rapidly added. The reaction mixture is stirred at ambient temperature for 16 hours, and then concentrated under reduced pressure. The residue is taken up in a mixture of 32 ml of water and 15 ml of ethyl acetate, and then the resulting product is stirred at ambient temperature for 3 hours. The precipitate formed is filtered off, and then rinsed successively with water, diisopropyl ether and diethyl ether. The solid obtained is dried with suction, and then dried under reduced pressure at 40° C. 485 mg of 2-[2-(4-chloro-2-methyl-2,3-dihydro-1H-indol-1-yl)-2-oxoethyl]-6-(morpholin-4-yl)pyrimidin-4(3H)-one are thus obtained in the form of a white crystalline powder, the characteristics of which are the following:

Workup

  1. stirringThe reaction mixture is stirred at ambient temperature for 16 hours
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue is taken up in a mixture of 32 ml of water and 15 ml of ethyl acetate
  4. stirringthe resulting product is stirred at ambient temperature for 3 hours
  5. customThe precipitate formed
  6. filtrationis filtered off
  7. washrinsed successively with water, diisopropyl ether and diethyl ether
  8. customThe solid obtained
  9. customis dried with suction
  10. customdried under reduced pressure at 40° C

Sources & evidence

ORD record
ord-7ba126475787426f9bcb2d5378ea0642
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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