Ethylamine → N-ethyl-4-methyl-3-(1-morpholinophthalazin-6-yl)benzamide

HRID 2357594Notes

Reaction equation

HRID 2357594 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[N:16][N:15]=[CH:14]2.[CH:27]([N:30](C(C)C)CC)(C)[CH3:28].C(N)C>S(Cl)(Cl)=O.O1CCCC1.CCOC(C)=O>[CH2:27]([NH:30][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[C:17]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[N:16][N:15]=[CH:14]3)[CH:4]=1)[CH3:28]

Participants

7

Reactant 3

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 251930634-Methyl-3-(1-morpholinophthalazin-6-yl)benzoic acid

Product 1

HCID 68453711N-ethyl-4-methyl-3-(1-morpholinophthalazin-6-yl)benzamide

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
65 °C

Procedure

4-Methyl-3-(1-morpholinophthalazin-6-yl)benzoic acid (100 mg, 286 μmol) was dissolved in thionyl chloride (5.7 mL) and heated to 65° C. for 1 h before being concentrated via rotovap. The crude reaction was dissolved in tetrahydrofuran 99.9% (5.7 mL) and diisopropylethylamine (150 μL, 859 μmol) and ethylamine—2 M in THF (0.71 mL) was added at 0° C. The reaction mixture was warmed to ambient temperature and stirred for 3 h. The reaction mixture was diluted with 50 mL of EtOAc, added to an addition funnel, partitioned with sodium bicarbonate (saturated, aqueous). The organic layers were washed 3 times with 50 mL of sodium bicarbonate (saturated, aqueous), combined, dried over sodium sulfate, and concentrated via rotovap to give a crude product. After purification by chromatography, the title compound was obtained. Found MS (ES+): 377(M+H)+.

Workup

  1. concentrationbefore being concentrated via rotovap
  2. customThe crude reaction
  3. temperatureThe reaction mixture was warmed to ambient temperature
  4. additionadded to an addition funnel
  5. custompartitioned with sodium bicarbonate (saturated, aqueous)
  6. washThe organic layers were washed 3 times with 50 mL of sodium bicarbonate (saturated, aqueous)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated via rotovap
  9. customto give a crude product
  10. customAfter purification by chromatography

Sources & evidence

ORD record
ord-9a4d91b2e88548878905d4a9f1428793
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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