Water → HCID 136138819, compound

HRID 2278514Notes

Reaction equation

HRID 2278514 reaction equation
[Br: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>[Br: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 67184N-bromobutanimideHCID 1355651592-{2-[(2S)-2-Methyl-2,3-dihydro-1H-indol-1-yl]-2-oxoethyl}-6-(4-morpholinyl)-4(1H)-pyrimidinone

Product 1

HCID 136138819HCID 136138819, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

100 mg of N-bromosuccinimide are added to a solution of 200 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 30 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 to 96/04 dichloromethane/methanol gradient, so as to give 93 mg of 5-bromo-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-c436a90d7d9042fdb32fa947b4b07f35
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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