Lithium Hydroxide → HCID 68455974, compound

HRID 2357653Notes

Reaction equation

HRID 2357653 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=3[CH3:23])[C:16](OC)=[O:17])=[CH:10][CH:11]=2)[CH:6]=[N:5][N:4]=1)#[N:2].[Li+].[OH-:25].CN(C(ON1N=NC2[CH:37]=[CH:38][CH:39]=[N:40]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(N)CC1>C1COCC1.O.C(OCC)(=O)C>[CH:39]1([NH:40][C:16]([C:15]2[CH:20]=[CH:21][C:22]([CH3:23])=[C:13]([C:9]3[CH:8]=[C:7]4[C:12](=[CH:11][CH:10]=3)[C:3]([C:1]([NH2:2])=[O:25])=[N:4][N:5]=[CH:6]4)[CH:14]=2)=[O:17])[CH2:37][CH2:38]1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 69828CyclopropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68455479HCID 68455479, compound

Product 1

HCID 68455974HCID 68455974, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

Methyl 3-(1-cyanophthalazin-6-yl)-4-methylbenzoate (120 mg, 396 μmol) was dissolved in THF/water (4:1) (3.96 mL) and LiOH (19 mg, 791 μmol) was added. The reaction mixture was stirred at 50° C. for 5.5 h, concentrated, and lyophilyzed under house vacuum. The reaction mixture was dissolved in DMF (791 μl) and HATU (301 mg, 791 μmol) and cyclopropylamine (277 μl, 3956 μmol) were added and the mixture was stirred at RT for 16 h. The mixture was diluted with 100 mL ethyl acetate, and partitioned with sodium bicarbonate (saturated, aqueous). The organic layers were washed 3×20 mL with sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, concentrated in vacuo, and purified by HPLC to give the title compound. MS (ES+): 347 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe reaction mixture was dissolved in DMF (791 μl)
  3. stirringthe mixture was stirred at RT for 16 h
  4. custompartitioned with sodium bicarbonate (saturated, aqueous)
  5. washThe organic layers were washed 3×20 mL with sodium bicarbonate (saturated, aqueous)
  6. customseparated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. custompurified by HPLC

Sources & evidence

ORD record
ord-ca0fd3987ace4388b1ac43beffeef1bd
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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