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Morpholine → HCID 68456406, compound

HRID 2357655
Notes
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Reaction equation

HRID 2357655 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-].[K+].N1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CN(C([O:41]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CCO.O.C(OCC)(=O)C>[CH:19]1([NH:18][C:16](=[O:17])[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]([N:2]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[O:41])=[N:4][N:5]=[CH:6]4)[CH:14]=2)[CH2:20][CH2:21]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8083MorpholineHCID 14797Potassium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68452746HCID 68452746, compound

Product 1

HCID 68456406HCID 68456406, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent
HCID 19096565Water ethanolSolvent

Conditions

Temperature
120 °C

Procedure

3-(1-Cyanophthalazin-6-yl)-N-cyclopropyl-4-methylbenzamide (115 mg, 350 μmol) was dissolved in EtOH/water (1:1) (3.50 mL) with potassium hydroxide (39 mg, 700 μmol) and heated in a microwave oven for 15 min at 120° C. The reaction mixture was concentrated in vacuo and dissolved in DMF (700 μl) and morpholine (152 μl, 1751 μmol) to which HATU (399 mg, 1051 μmol) was added. The reaction was stirred at RT for 16 h, then diluted with ethyl acetate, filtered, diluted with 50 mL ethyl acetate, and partitioned with sodium bicarbonate (saturated, aqueous). The organic layers were washed 2×20 mL with sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, concentrated in vacuo, and purified by flash chromatography to give the title compound. MS (ES+): 417 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in DMF (700 μl)
  3. filtrationfiltered
  4. additiondiluted with 50 mL ethyl acetate
  5. custompartitioned with sodium bicarbonate (saturated, aqueous)
  6. washThe organic layers were washed 2×20 mL with sodium bicarbonate (saturated, aqueous)
  7. customseparated
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. custompurified by flash chromatography

Sources & evidence

ORD record
ord-7b2d9d0804554d5f8a83bee72b8ab60d
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07759337B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes