Potassium Carbonate → HCID 57629489, compound

HRID 2108356Notes

Reaction equation

HRID 2108356 reaction equation
[CH:1]1([C:4]2[CH:8]=[C:7]([NH2:9])[NH:6][N:5]=2)[CH2:3][CH2:2]1.Cl.Cl[CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH:1]1([C:4]2[CH:8]=[C:7]([NH2:9])[N:6]([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 178507266HCID 178507266, compound

Product 1

HCID 57629489HCID 57629489, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-cyclopropyl-1H-pyrazole-5-amine (250 mg, 2.0 mmol), 4-(2-chloroethyl)morpholine HCl salt (372 mg, 2.0 mmol) and potassium carbonate (829 mg, 6.0 mmol) in dry DMF (10 mL) was stirred at room temperature overnight. After being diluted with ethyl acetate (50 mL), the reaction mixture was filtered through a pad of Celite and rinsed with ethyl acetate (2×15 mL). The combined filtrates were concentrated in vacuo and purified by ISCO (CH2Cl2-MeOH—NH4OH: 100:0:0 to 90:10:1) on silica gel to afford the desired amino-pyrazole.

Workup

  1. filtrationthe reaction mixture was filtered through a pad of Celite
  2. washrinsed with ethyl acetate (2×15 mL)
  3. concentrationThe combined filtrates were concentrated in vacuo
  4. custompurified by ISCO (CH2Cl2-MeOH—NH4OH: 100:0:0 to 90:10:1) on silica gel

Sources & evidence

ORD record
ord-e7d41bef01e34ee0a96264c8afa52b0e
Source dataset
uspto-grants-2009_04
Patent number
US07514435B2

Reaction notes

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