Water → HCID 57581497, compound

HRID 1951160Notes

Reaction equation

HRID 1951160 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Cl:12])=[N:4][N:3]=1.[CH3:13][C@H:14]1[CH2:19][NH:18][CH2:17][CH2:16][N:15]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(N(CC)CC)C.O>CS(C)=O>[Cl:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([N:18]2[CH2:17][CH2:16][N:15]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@@H:14]([CH3:13])[CH2:19]2)=[N:3][N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 784901,4-DichlorophthalazineHCID 10081508tert-Butyl (2S)-2-methylpiperazine-1-carboxylate

Product 1

HCID 57581497HCID 57581497, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Heat a mixture of 1,4-dichlorophthalazine (7.80 g, 39.2 mmol), (S)-tert-butyl 2-methylpiperazine-1-carboxylate (4.98 g, 24.9 mmol) and triethylamine (10.3 mL, 73.9 mmol) in DMSO (110 mL) at 80° C. for 18 h. Pour the reaction mixture into water, rinsing with EtOAc. Extract with EtOAc. Wash the organic layer with water (2×) and brine, and 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 (4.13 g, 46%). ES/MS m/z (35Cl) 363.0 (M+1).

Workup

  1. temperatureHeat
  2. washrinsing with EtOAc
  3. extractionExtract with EtOAc
  4. washWash the organic layer with water (2×) and brine
  5. dry with materialdry 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-0908e072b72441ed99e1ab916a86f698
Source dataset
uspto-grants-2013_03
Patent number
US08404687B2

Reaction notes

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