Sodium Carbonate → HCID 178481935, compound

HRID 510453Notes

Reaction equation

HRID 510453 reaction equation
C(OC(=O)[NH:7][C:8]1[C:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=2[Cl:21])=[C:11]([OH:22])[N:10]([CH3:23])[N:9]=1)(C)(C)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:7][C:8]1[C:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=2[Cl:21])=[C:11]([OH:22])[N:10]([CH3:23])[N:9]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 178481936HCID 178481936, compound

Product 1

HCID 178481935HCID 178481935, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of tert-butyl(4-(2,3-dichlorobenzyl)-5-hydroxy-1-methyl-1H-pyrazol-3-yl)carbamate (15 g, 40 mmol) in DCM (150 mL), TFA (10 mL) was added dropwise at room temperature with stirring. The reaction mixture was stirred at room temperature overnight. Then the pH of the reaction mixture was adjusted to 10 with aq. Na2CO3, and extracted with DCM (100 mL*3). The combined organic layers were washed with brine, dried over Na2SO4, filtered and the filtrate was concentrated to provide the titled compound (7 g, 63%), as a white solid; LC/MS: MS (ES+) m/e 272 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.90 (s, 3H), 3.45 (s, 2H), 6.06 (s, 2H), 7.01 (d, J=7.8 Hz, 1H), 7.25 (t, J=7.8 Hz, 1H), 7.45 (d, J=7.8 Hz, 1H), 8.95 (s, 1H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. extractionextracted with DCM (100 mL*3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cb3a9d9d127244f1a59a83566fb5329c
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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