Water → HCID 136069583, compound

HRID 2278512Notes

Reaction equation

HRID 2278512 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][C@H:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]1[C:19](=[O:34])[CH2:20][C:21]1[NH:26][C:25](=[O:27])[CH:24]=[C:23]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[N:22]=1.O.ClCCl>C(Cl)(Cl)Cl>[Cl:1][C:24]1[C:25](=[O:27])[NH:26][C:21]([CH2:20][C:19]([N:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:18][C@@H:10]2[CH3:9])=[O:34])=[N:22][C:23]=1[N:28]1[CH2:29][CH2:30][O:31][CH2:32][CH2:33]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 31398ChlorosuccinimideHCID 1355651592-{2-[(2S)-2-Methyl-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-6-(4-morpholinyl)-4(1H)-pyrimidinone

Product 1

HCID 136069583HCID 136069583, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

37.6 mg of N-chlorosuccinimide are added to a solution of 100 mg of 2-{2-[(2S)-2-methyl-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-6-(morpholin-4-yl)pyrimidin-4(3H)-one in 4 ml of chloroform. The reaction medium is stirred at ambient temperature for 2 hours. 5 ml of water and 20 ml of dichloromethane are added. After settling out, the organic phase is dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue obtained is purified on a silica column, eluent: 99/01 then 98/02 then 97/03 dichloromethane/methanol, so as to give 69 mg of 5-chloro-2-[2-((S)-2-methyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one, the characteristics of which are the following:

Workup

  1. dry with materialthe organic phase is dried over magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue obtained
  5. customis purified on a silica column, eluent

Sources & evidence

ORD record
ord-049311cfaec041d9b9aef42d502ba7a9
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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