1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 136069612, compound

HRID 2278624Notes

Reaction equation

HRID 2278624 reaction equation
N1(C2N=C(CC([O-])=O)NC(=O)C=2)CCOCC1.[Na+].[ClH:19].CN(C)CCCN=C=NCC.CO[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39]1[CH:47]=[CH:46][CH:45]=[C:44]2[C:40]=1[CH2:41][CH2:42][N:43]2[C:48](=[O:63])[CH2:49][C:50]1[NH:55][C:54](=[O:56])[CH:53]=[C:52]([N:57]2[CH2:62][CH2:61][O:60][CH2:59][CH2:58]2)[N:51]=1>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:19][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39]1[CH:47]=[CH:46][CH:45]=[C:44]2[C:40]=1[CH2:41][CH2:42][N:43]2[C:48](=[O:63])[CH2:49][C:50]1[NH:55][C:54](=[O:56])[CH:53]=[C:52]([N:57]2[CH2:62][CH2:61][O:60][CH2:59][CH2:58]2)[N:51]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetateHCID 136069606HCID 136069606, compound

Product 1

HCID 136069612HCID 136069612, compoundYield 110.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

300 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (example 1d, step 2d), 330 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 6 ml of pyridine are successively added to a solution of 264 mg of 4-(2-chlorophenyl)-2,3-dihydro-1H-indole (reference example 6d) in 5 ml of pyridine. The reaction mixture is stirred at ambient temperature for 4 days. The reaction medium is diluted with ethyl acetate (60 ml) and then successively washed with an aqueous 1M hydrochloric acid solution, an aqueous 1M sodium hydroxide solution, and a saturated aqueous sodium chloride solution. The organic phase is then dried over magnesium sulfate and filtered through sintered glass. A precipitate appears after a few hours, which is then filtered off through sintered glass and washed with diethyl ether. 294 mg of 2-{2-[4-(2-chlorophenyl)-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 1M hydrochloric acid solution
  2. dry with materialThe organic phase is then dried over magnesium sulfate
  3. filtrationfiltered through sintered glass
  4. waitA precipitate appears after a few hours
  5. filtrationwhich is then filtered off through sintered glass
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-45248d94dd8942f097b27bdaead5e9ef
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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