Ethyl Acetate → HCID 59557969, compound

HRID 221876Notes

Reaction equation

HRID 221876 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([S:13]([NH:16][CH2:17][CH2:18][O:19][CH3:20])(=[O:15])=[O:14])[CH:10]=[CH:11][CH:12]=2)[N:5]=[C:4]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:31]1([O:37][C:38](Cl)=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(OCC)(=O)C>C1COCC1>[C:31]1([O:37][C:38](=[O:39])[NH:1][C:2]2[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([S:13](=[O:14])(=[O:15])[NH:16][CH2:17][CH2:18][O:19][CH3:20])[CH:8]=3)[N:5]=[C:4]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:3]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 15891Phenyl chloroformateHCID 59557921HCID 59557921, compound

Product 1

HCID 59557969HCID 59557969, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-(5-amino-3-tert-butyl-pyrazol-1-yl)-N-(2-methoxyethyl)benzene sulfonamide (940 mg, 2.67 mmol) and solid sodium carbonate (493 mg, 5.87 mmol, 2.2 eq) in anhydrous THF was slowly added phenylchloroformate (0.40 mL, 3.20 mmol, 1.2 eq), and the reaction mixture was stirred at room temperature under nitrogen for 6 h. The reaction mixture was poured into ethyl acetate, and then the organic phase was separated and washed with water and brine, dried over Na2SO4, filtered, and concentrated at reduced pressure. Purification by MPLC (35% EtOAc/hexane) afforded the title compound (887 mg, 70%) as a white solid. 1H-NMR (CD3OD) δ 10.17 (broad s, 1H), 7.94 (t, J=1.5 Hz, 1H), 7.89 (t, J=6.0 Hz, 1H), 7.81 to 7.69 (m, 3H), 7.34 to 7.29 (m, 2H), 7.19 (t, J=7.2 Hz, 1H), 7.09 (broad s, 2H), 6.38 (s, 1H), 3.25 (t, J=6.0 Hz, 2H), 3.09 (s, 3H), 2.90 (broad s, 2H), 1.26 (s, 9H).

Workup

  1. customthe organic phase was separated
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure
  6. customPurification by MPLC (35% EtOAc/hexane)

Sources & evidence

ORD record
ord-33eed90256c147229324fee8441dcc93
Source dataset
uspto-grants-2012_06
Patent number
US08207166B2

Reaction notes

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