Potassium Carbonate → HCID 59428130, compound

HRID 1480906Notes

Reaction equation

HRID 1480906 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:16]([N:22]3[CH:26]=[C:25]([C:27]([OH:29])=O)[CH:24]=[N:23]3)=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[NH:36]1[CH:40]=[CH:39]N=N1.C([O-])([O-])=O.[K+].[K+].S1(CCCC1)(=O)=O>C(O)(=O)C.ClCCl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[C:16]([N:22]3[CH:26]=[C:25]([C:27]4[O:29][CH:39]=[CH:40][N:36]=4)[CH:24]=[N:23]3)=[N:17][CH:18]=[C:19]([Cl:21])[CH:20]=2)(=[O:12])=[O:13])=[CH:9][CH:10]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 31347SulfolaneHCID 65578Oxalyl chlorideHCID 59428113HCID 59428113, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 59428130HCID 59428130, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A 25 mL scintillation vial was charged with 1-[3-(4-tert-butyl-benzenesulfonylamino)-5-chloro-pyridin-2-yl]-1H-pyrazole-4-carboxylic acid (87 mg, 0.2 mmol), oxalyl chloride (2 mL, 1.0 M solution in dichloromethane), and dichloromethane (3 mL). The mixture was stirred at room temperature for 2 hours, the volatiles removed in vacuo, and the residue further dried at reduced pressure for 4 hours. The scintillation vial containing the crude acid chloride was subsequently charged with 1H-1,2,3-triazole (34 mg, 0.5 mmol), K2CO3 (138 mg, 1.0 mmol), and sulfolane (2 mL). The vial was sealed and stirred at 80° C. for 16 hours. The reaction solution was neutralized to pH=7 with glacial acetic acid. The mixture was extracted with ethyl acetate (2×10 mL) and the combined organics were concentrated in vacuo. The residue was purified via preparative HPLC to afford 4-tert-butyl-N-[5-chloro-2-(4-oxazol-2-yl-pyrazol-1-yl)-pyridin-3-yl]-benzenesulfonamide as a white powder: MS (ES) M+H expected 458.1, found 458.0.

Workup

  1. customthe volatiles removed in vacuo
  2. customthe residue further dried at reduced pressure for 4 hours
  3. additionThe scintillation vial containing the crude acid chloride
  4. customThe vial was sealed
  5. stirringstirred at 80° C. for 16 hours
  6. extractionThe mixture was extracted with ethyl acetate (2×10 mL)
  7. concentrationthe combined organics were concentrated in vacuo
  8. customThe residue was purified via preparative HPLC

Sources & evidence

ORD record
ord-13a4733964524577a09833247aaca21d
Source dataset
uspto-grants-2016_08
Patent number
US09409909B2

Reaction notes

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