Dimethylcarbamoyl Chloride → HCID 59240613, compound

HRID 42193Notes

Reaction equation

HRID 42193 reaction equation
[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[N:29]=[CH:28][C:27]([CH2:30][OH:31])=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:34][N:35]([CH3:39])[C:36](Cl)=[O:37]>C1COCC1>[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[N:29]=[CH:28][C:27]([CH2:30][O:31][C:36](=[O:37])[N:35]([CH3:39])[CH3:34])=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 24758Sodium hydride2×HCID 44186314HCID 44186314, compound

Product 1

HCID 59240613HCID 59240613, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{6-[4-(4-Benzyl-phthalazin-1-yl)-piperazin-1-yl]-pyridin-3-yl}-methanol (75 mg, 0.182 mmol) is dissolved in THF (1 mL) and added to a flask containing NaH (7.5 mg, 0.188 mmol). Stir 1 h at room temperature. Add dimethyl carbamoyl chloride (22 mg, 2.096 mmol) and stir for 16 h at room temperature. Incomplete conversion observed. Reaction is heated to 60° C. and stirred 16 h. Add additional NaH (7.5 mg, 0.188 mmol) is added and reaction quickly reaches 95% conversion. Concentrate reaction mixture in vacuo. The residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2) to afford the title compound (24 mg, 27%).

Workup

  1. additionadded to a flask
  2. customReaction
  3. temperatureis heated to 60° C.
  4. stirringstirred 16 h
  5. additionis added
  6. customreaction quickly reaches 95% conversion
  7. concentrationConcentrate
  8. customreaction mixture in vacuo
  9. customThe residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-4bc01c26076341bc9a73487b36911a30
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

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