Carbon Dioxide → HCID 58379073, compound

HRID 1951164Notes

Reaction equation

HRID 1951164 reaction equation
CO.C(=O)=O.C(Cl)(=O)C.[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([N:27]3[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[C@@H:29]([CH3:40])[CH2:28]3)=[N:19][N:18]=2)=[CH:13][CH:12]=1>CC(C)=O.O>[F:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]([N:27]3[CH2:32][CH2:31][NH:30][C@@H:29]([CH3:40])[CH2:28]3)=[N:19][N:18]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 887MethanolHCID 6367Acetyl chlorideHCID 58378949HCID 58378949, compound

Product 1

HCID 58379073HCID 58379073, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

Cool methanol (2.82 L) to 0° C. via a 1:1 acetone/water bath with dry ice, and add acetyl chloride (142 mL, 2.0 mol) dropwise over a period of 30 min, maintaining the temperature below 15° C. during the addition. Stir the mixture for 15 min. Add (S)-tert-butyl 4-(4-(4-fluorophenyl)phthalazin-1-yl)-2-methylpiperazine-1-carboxylate (282 g, 667 mmol) in one portion. Stir the mixture for 12 h at 25° C. Concentrate, and dissolve the residue in water (3.0 L). Add solid NaHCO3 until the pH is 7. Extract the product with CH2Cl2 (2×2.0 L), combine the organic layers, and concentrate to give the title compound as a brown crushable foam in quantitative yield (236 g, >100%). ES/MS m/z 323.0 (M+1).

Workup

  1. temperaturemaintaining the temperature below 15° C.
  2. additionduring the addition
  3. stirringStir the mixture for 12 h at 25° C
  4. concentrationConcentrate
  5. dissolutiondissolve the residue in water (3.0 L)
  6. additionAdd solid NaHCO3 until the pH is 7
  7. extractionExtract the product with CH2Cl2 (2×2.0 L)
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-4310e33463d341358fb6fedd60176182
Source dataset
uspto-grants-2013_03
Patent number
US08404687B2

Reaction notes

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