Diisopropylethylamine → HCID 57581497, compound

HRID 1689955Notes

Reaction equation

HRID 1689955 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][NH:15][C@@H:14]([CH3:18])[CH2:13]2)=[N:4][N:3]=1.[C:19]([O:23][C:24](=O)[O:25]C(C)(C)C)([CH3:22])([CH3:21])[CH3:20].C(N(CC)C(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][N:15]([C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:25])[C@@H:14]([CH3:18])[CH2:13]2)=[N:4][N:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 57581479HCID 57581479, compound

Product 1

HCID 57581497HCID 57581497, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-1-chloro-4-(3-methylpiperazin-1-yl)phthalazine (1.50 g, 5.71 mmol) and di-t-butylcarbonate (1.73 g, 6.56 mmol) were dissolved in DMF (12 mL) and N,N-diisopropylethylamine (2 mL) and stirred at rt for 4 hours. The reaction was taken up in ethyl acetate (150 mL) and washed with aqueous K2CO3 (10%), water, and saturated sodium chloride. The organics were dried (MgSO4) and evaporated to give a yellow oil. Chromatography over silica gel with a gradient of hexanes/0-40% ethyl acetate gave an off-white solid. MS (M+H)+=363.1.

Workup

  1. washwashed with aqueous K2CO3 (10%), water, and saturated sodium chloride
  2. dry with materialThe organics were dried (MgSO4)
  3. customevaporated
  4. customto give a yellow oil

Sources & evidence

ORD record
ord-e3bfccb9a900465190a44ba76df2e277
Source dataset
uspto-grants-2012_04
Patent number
US08153633B2

Reaction notes

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