Water → HCID 58379021, compound

HRID 1951157Notes

Reaction equation

HRID 1951157 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.[CH2:19]([C@H:21]1[CH2:26][NH:25][CH2:24][CH2:23][N:22]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH3:20].C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[CH2:19]([C@H:21]1[CH2:26][N:25]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[N:4][N:3]=2)[CH2:24][CH2:23][N:22]1[C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 21152391-Chloro-4-(4-fluorophenyl)phthalazineHCID 17750462(S)-2-Ethylpiperazine, N1-BOC protected

Product 1

HCID 58379021HCID 58379021, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Heat a mixture of 1-chloro-4-(4-fluorophenyl)phthalazine (5.02 g, 19.4 mmol), (S)-tert-butyl 2-ethylpiperazine-1-carboxylate (5.00 g, 23.3 mmol) and K2CO3 (5.38 g, 38.9 mmol) in DMSO (75 mL) at 120° C. for 1 d. Pour the reaction mixture into water, rinsing with EtOAc. Extract with EtOAc. Wash the organic layer with water (2×), then brine, dry over Na2SO4, and concentrate under reduced pressure. Purify the resulting residue by flash silica gel chromatography (gradient of 20 to 80% EtOAc in hexanes) to provide the title compound (5.11 g, 60%). ES/MS m/z 437.2 (M+1).

Workup

  1. temperatureHeat
  2. washrinsing with EtOAc
  3. extractionExtract with EtOAc
  4. washWash the organic layer with water (2×)
  5. dry with materialbrine, dry over Na2SO4
  6. concentrationconcentrate under reduced pressure
  7. customPurify the resulting residue by flash silica gel chromatography (gradient of 20 to 80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8ee519979dc9466d8aa2cd852e9820af
Source dataset
uspto-grants-2013_03
Patent number
US08404687B2

Reaction notes

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