Isopropylamine → 6-[5-[(Cyclopropylamino)carbonyl]-2-methylphenyl]-N-(1-methylethyl)-1-phthalazinecarboxamide

HRID 2357630Notes

Reaction equation

HRID 2357630 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:14]=[C:15]([CH:22]=[CH:23][C:24]=3[CH3:25])[C:16]([NH:18][CH:19]3[CH2:21][CH2:20]3)=[O:17])=[CH:10][CH:11]=2)[CH:6]=[N:5][N:4]=1)#[N:2].[OH-:26].[K+].CN(C(ON1N=N[C:38]2[CH:39]=CC=N[C:37]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N)(C)C>C(O)C.O.C(OCC)(=O)C>[CH:19]1([NH:18][C:16]([C:15]2[CH:22]=[CH:23][C:24]([CH3:25])=[C:13]([C:9]3[CH:8]=[C:7]4[C:12](=[CH:11][CH:10]=3)[C:3]([C:1]([NH:2][CH:38]([CH3:39])[CH3:37])=[O:26])=[N:4][N:5]=[CH:6]4)[CH:14]=2)=[O:17])[CH2:20][CH2:21]1

Participants

7

Reactant 4

HCID 6363IsopropylamineHCID 14797Potassium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 68452746HCID 68452746, compound

Product 1

HCID 684556306-[5-[(Cyclopropylamino)carbonyl]-2-methylphenyl]-N-(1-methylethyl)-1-phthalazinecarboxamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 19096565Water ethanolSolvent

Procedure

3-(1-Cyanophthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide (115 mg, 350 μmol) and potassium hydroxide (39 mg, 700 μmol) were dissolved in ethanol/water (1:1) (3.50 mL) before it was placed in the microwave for 10 min at 120° C. The reaction mixture was concentrated before it was dissolved in dimethylformamide (700 μl); HATU (266 mg, 700 μmol) and isopropylamine (150 μl, 1751 μmol) were added. This was stirred at RT for 16 h before more HATU was added, and the reaction mixture was stirred at RT for 7 h. The reaction mixture was diluted with 100 mL of ethyl acetate, added to a separatory funnel, partitioned with water, washed 2× with 50 mL of water, separated, dried over sodium sulfate, concentrated in vacuo, and purified by HPLC to give the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated before it
  2. dissolutionwas dissolved in dimethylformamide (700 μl)
  3. additionwas added
  4. additionadded to a separatory funnel
  5. custompartitioned with water
  6. washwashed 2× with 50 mL of water
  7. customseparated
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. custompurified by HPLC

Sources & evidence

ORD record
ord-7787cc5079e646c0a36830e81bb265de
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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