Citric Acid → HCID 25012898, compound

HRID 589586Notes

Reaction equation

HRID 589586 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([C:9]1[CH:14]=[C:13]([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=3)[N:19]=2)[CH:12]=[CH:11][N:10]=1)[CH2:7][CH3:8].N1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[CH2:6]([C:9]1[CH:14]=[C:13]([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:21]=[CH:22][C:23]([NH:26][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:24][CH:25]=3)[N:19]=2)[CH:12]=[CH:11][N:10]=1)[CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 25012739HCID 25012739, compound

Product 1

HCID 25012898HCID 25012898, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In reaction (d) methanesulfonyl chloride (0.23 mL, 2.97 mmol) was added to a stirred solution of 16 (800 mg, 2.71 mmol) and pyridine (0.66 mL, 8.1 mmol) in CH2Cl2 (20 mL) at 0° C. After being stirred for 0.5 h, the mixture was poured into 2 M citric acid solution and extracted with EtOAc. The combined extracts were washed with saturated NaHCO3 solution and brine, dried over Na2SO4, and concentrated to produce N-(4-(2-(2-propylpyridin-4-yl)thiazol-4-yl)phenyl)methanesulfonamide 19 (880 mg, 87%) as a yellow foam.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6b7eaa6615ca41c7b89fe9331570f9ec
Source dataset
uspto-grants-2016_01
Patent number
US09233941B2

Reaction notes

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