Sodium Hydroxide → HCID 86686699, compound

HRID 572092Notes

Reaction equation

HRID 572092 reaction equation
[OH-].[Na+].[C:3]1([CH3:15])[CH:8]=[CH:7][C:6]([N:9]2[C:13]([NH2:14])=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1.Cl[C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18]>O.CCOC(C)=O>[Cl:22][C:21]([Cl:24])([Cl:23])[CH2:20][O:19][C:17](=[O:18])[NH:14][C:13]1[N:9]([C:6]2[CH:5]=[CH:4][C:3]([CH3:15])=[CH:8][CH:7]=2)[N:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 215851111-(4-Methylphenyl)-1H-pyrazol-5-amine

Product 1

HCID 86686699HCID 86686699, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

NaOH (107 mg, 2.67 mmol) was added to a stirred solution of 2-p-tolyl-2H-pyrazol-3-ylamine (for reference procedure see WO 2009/150614, which is incorporated herein by reference in its entirety, 346 mg, 2.00 mmol) in water (1 mL) and EtOAc (4 mL). The mixture was cooled to 0° C., and 2,2,2-trichloroethyl chloroformate (385 μL, 2.80 mmol) added. Stirring was continued for 30 min at 0° C. and then for 2 h at RT. The mixture was partitioned between water and EtOAc. The organic phase was washed with brine and concentrated to dryness in vacuo to give the title compound as an orange residue. LCMS (Method 3): Rt 3.90 min, m/z 348, 350 [MH+].

Workup

  1. waitfor 2 h at RT
  2. customThe mixture was partitioned between water and EtOAc
  3. washThe organic phase was washed with brine
  4. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-1589bdbec8f54303b53109157ba5f690
Source dataset
uspto-grants-2015_05
Patent number
US09029373B2

Reaction notes

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