Water → HCID 58378949, compound

HRID 1951154Notes

Reaction equation

HRID 1951154 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[N:4][N:3]=1.[CH3:19][C@H:20]1[CH2:25][NH:24][CH2:23][CH2:22][N:21]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].C(N(CC)CC)C.O>CS(C)=O>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([N:24]3[CH2:23][CH2:22][N:21]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@@H:20]([CH3:19])[CH2:25]3)=[N:3][N:4]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 21152391-Chloro-4-(4-fluorophenyl)phthalazineHCID 10081508tert-Butyl (2S)-2-methylpiperazine-1-carboxylate

Product 1

HCID 58378949HCID 58378949, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Heat a mixture of 1-chloro-4-(4-fluorophenyl)phthalazine (5.0 g, 19.3 mmol), (S)-tert-butyl 2-methylpiperazine-1-carboxylate (5.03 g, 25.1 mmol) and triethylamine (8.1 mL, 59.0 mmol) in DMSO (97 mL) at 115° C. for 3 d. Pour the reaction mixture into water, rinsing with CH2Cl2. Extract with Et2O. Wash the organic layer with water (2×), then dry over Na2SO4 and concentrate under reduced pressure. Purify the resulting residue by flash silica gel chromatography (gradient of 0 to 20% EtOAc in CH2Cl2) to provide the title compound as a pale yellow foam (7.05 g, 84%). ES/MS m/z 423.2 (M+1).

Workup

  1. temperatureHeat
  2. washrinsing with CH2Cl2
  3. extractionExtract with Et2O
  4. washWash the organic layer with water (2×)
  5. dry with materialdry over Na2SO4
  6. concentrationconcentrate under reduced pressure
  7. customPurify the resulting residue by flash silica gel chromatography (gradient of 0 to 20% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-5f1491ef83a6478fbaa5a16c954b8234
Source dataset
uspto-grants-2013_03
Patent number
US08404687B2

Reaction notes

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