1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 136069616, compound

HRID 2278628Notes

Reaction equation

HRID 2278628 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH2:10][CH2:11][NH:12]2.Cl.CN(C)CCCN=C=NCC.[N:29]1([C:35]2[N:36]=[C:37]([CH2:42][C:43]([O-])=[O:44])[NH:38][C:39](=[O:41])[CH:40]=2)[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.[Na+]>N1C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH2:10][CH2:11][N:12]2[C:43](=[O:44])[CH2:42][C:37]1[NH:38][C:39](=[O:41])[CH:40]=[C:35]([N:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)[N:36]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 76846507HCID 76846507, compoundHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136069616HCID 136069616, compoundYield 79.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

115 mg of 4-(2-fluorophenyl)-2,3-dihydro-1H-indole (diluted in 3 ml of pyridine) and 125 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride are successively added to a solution of 211 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (example 1d, step 2d) in 3 ml of pyridine. The reaction mixture is stirred at ambient temperature for 3 days. The reaction medium is diluted in ethyl acetate (100 ml) and then successively washed with an aqueous 1N hydrochloric acid solution, an aqueous 1N sodium hydroxide solution and a saturated aqueous sodium chloride solution. The organic phase is then dried over magnesium sulfate, filtered through sintered glass, and concentrated under reduced pressure. 187 mg of 2-{2-[4-(2-fluorophenyl)-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-6-(morpholin-4-yl)pyrimidin-4(3H)-one are obtained in the form of a beige solid, the characteristics of which are the following:

Workup

  1. washsuccessively washed with an aqueous 1N hydrochloric acid solution
  2. dry with materialThe organic phase is then dried over magnesium sulfate
  3. filtrationfiltered through sintered glass
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a2a7bb323c9f47c7937667d987537719
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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