1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 136378694, compound

HRID 2278644Notes

Reaction equation

HRID 2278644 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH3:13][CH:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[C:23]([F:26])([F:25])[F:24])[NH:15]1.[N:27]1([C:33]2[N:34]=[C:35]([CH2:40][C:41]([O-])=[O:42])[NH:36][C:37](=[O:39])[CH:38]=2)[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.[Na+]>CN(C)C=O.N1C=CC=CC=1.O>[CH3:13][CH:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[C:23]([F:24])([F:26])[F:25])[N:15]1[C:41](=[O:42])[CH2:40][C:35]1[NH:36][C:37](=[O:39])[CH:38]=[C:33]([N:27]2[CH2:28][CH2:29][O:30][CH2:31][CH2:32]2)[N:34]=1

Participants

7

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57800076HCID 57800076, compoundHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136378694HCID 136378694, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

225 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 196 mg of 2-methyl-4-trifluoromethyl-2,3-dihydro-1H-indole are added to a solution of 259 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 and 3 ml of pyridine. The reaction mixture is stirred at ambient temperature for 20 hours and then diluted with water and extracted with ethyl acetate. The extracts are washed successively with water, a hydrochloric acid solution (1M), water and a saturated sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered, and concentrated under reduced pressure, so as to give 144 mg of 2-[2-(2-methyl-4-trifluoromethyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one in the form of a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts are washed successively with water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0154350cc8e34bee9a99acb0087d8208
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

Loading…