4-Methylmorpholine → HCID 86636865, compound

HRID 606028Notes

Reaction equation

HRID 606028 reaction equation
[CH:1]1([NH:4][C:5]2[C:10]([C:11]([OH:13])=O)=[CH:9][N:8]=[C:7]3[N:14]([CH2:17][CH3:18])[N:15]=[CH:16][C:6]=23)[CH2:3][CH2:2]1.Cl.[CH3:20][NH:21][O:22][CH3:23].OC1C2N=NNC=2C=CC=1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[CH:1]1([NH:4][C:5]2[C:10]([C:11]([N:21]([O:22][CH3:23])[CH3:20])=[O:13])=[CH:9][N:8]=[C:7]3[N:14]([CH2:17][CH3:18])[N:15]=[CH:16][C:6]=23)[CH2:2][CH2:3]1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66733147HCID 66733147, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 86636865HCID 86636865, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-cyclopropylamino-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (500 mg, 0.0020 mole) and N,O-dimethylhydroxylamine hydrochloride (298 mg, 0.0030 mole) were taken in dimethylformamide. At 0° C., hydroxybenzotriazole (550 mg, 0.0040 mole) and N-methylmorpholine (1.34 ml, 0.012 mole) were added and the reaction mixture was stirred for about 1 hour. 1-(3-dimethylaminopropyl) 3-ethyl carbodiimide hydrochloride (780 mg, 0.0040 mole) was added and the reaction mixture was stirred for about 14 hours. Water was added and extraction was carried out with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give an oily compound. Yield: 500 mg. m/z: (M++1) 290.2.

Workup

  1. stirringthe reaction mixture was stirred for about 14 hours
  2. extractionextraction
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give an oily compound

Sources & evidence

ORD record
ord-5f6cd106ee404be3990297f0dfa82aa7
Source dataset
uspto-grants-2011_03
Patent number
US07915286B2

Reaction notes

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