Water → HCID 58379057, compound

HRID 1951159Notes

Reaction equation

HRID 1951159 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[NH:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1.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:19]2[CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][C@@H:14]2[CH3:13])=[N:3][N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 784901,4-DichlorophthalazineHCID 7023035(S)-1-Boc-3-methylpiperazine

Product 1

HCID 58379057HCID 58379057, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Heat a mixture of 1,4-dichlorophthalazine (10.0 g, 50.2 mmol), (S)-tert-butyl 3-methylpiperazine-1-carboxylate (15.1 g, 75.4 mmol) and triethylamine (21.0 mL, 150.7 mmol) in DMSO (200 mL) at 120° C. for 2 d. Pour the reaction mixture into water, rinsing with CH2Cl2. Extract with Et2O. Wash the organic layer with water (2×), 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 solid (6.0 g, 33%). ES/MS m/z (35Cl) 363.0 (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-e6ebf607436d455a9568f1f1eab48bf3
Source dataset
uspto-grants-2013_03
Patent number
US08404687B2

Reaction notes

Loading…