Pyridine → HCID 136069609, compound

HRID 2278620Notes

Reaction equation

HRID 2278620 reaction equation
N1C=CC=CC=1.[N:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH2:15][CH2:16][NH:17]3)=[CH:9][CH:8]=1.Cl.CN(C)CCCN=C=NCC.[N:34]1([C:40]2[N:41]=[C:42]([CH2:47][C:48]([O-])=[O:49])[NH:43][C:44](=[O:46])[CH:45]=2)[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.[Na+]>CN(C)C=O>[N:34]1([C:40]2[N:41]=[C:42]([CH2:47][C:48](=[O:49])[N:17]3[C:18]4[C:14](=[C:13]([C:10]5[CH:11]=[CH:12][N:7]=[CH:8][CH:9]=5)[CH:21]=[CH:20][CH:19]=4)[CH2:15][CH2:16]3)[NH:43][C:44](=[O:46])[CH:45]=2)[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13276698HCID 13276698, compoundHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136069609HCID 136069609, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.2 ml of pyridine, 25 mg of 4-pyridin-4-yl-2,3-dihydro-1H-indole and 23 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are successively added to a solution of 26.7 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 filtered through sintered glass, and the precipitate is washed with water (2×1 ml) and oven-dried. 27.6 mg of 6-(morpholin-4-yl)-2-{2-oxo-2-[4-(pyridin-4-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. filtrationfiltered through sintered glass
  3. washthe precipitate is washed with water (2×1 ml)
  4. customoven-dried

Sources & evidence

ORD record
ord-78c7ead02dc04385ba9fff6ce84f955e
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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