5-Isopropyl-1,3,4-thiadiazol-2-amine → N-(5-Isopropyl-[1,3,4]thiadiazol-2-yl)-4-[2-(4-methoxy-phenyl)-oxazol-4-ylmethoxy]-benzenesulfonamide

HRID 604462Notes

Reaction equation

HRID 604462 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=3)[N:13]=2)=[CH:5][CH:4]=1.[CH:26]([C:29]1[S:33][C:32]([NH2:34])=[N:31][N:30]=1)([CH3:28])[CH3:27]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH:26]([C:29]1[S:33][C:32]([NH:34][S:22]([C:19]2[CH:20]=[CH:21][C:16]([O:15][CH2:14][C:12]3[N:13]=[C:9]([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[O:10][CH:11]=3)=[CH:17][CH:18]=2)(=[O:24])=[O:23])=[N:31][N:30]=1)([CH3:28])[CH3:27]

Participants

5

Reactant 2

HCID 1471515-Isopropyl-1,3,4-thiadiazol-2-amineHCID 575431834-[2-(4-Methoxy-phenyl)-oxazol-4-ylmethoxy]-benzenesulfonyl chloride

Product 1

HCID 16129045N-(5-Isopropyl-[1,3,4]thiadiazol-2-yl)-4-[2-(4-methoxy-phenyl)-oxazol-4-ylmethoxy]-benzenesulfonamideYield 2.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

580 mg 4-[2-(4-Methoxy-phenyl)-oxazol-4-ylmethoxy]-benzenesulfonyl chloride were added to a stirred solution of 275 mg 5-isopropyl-[1,3,4]thiadiazol-2-ylamine in 35 ml pyridine. 18 mg 4-Dimethylaminopyridine were added. The reaction mixture was stirred at room temperature overnight. The pyridine was removed in vacuo and the residue coevaporated with 15 ml toluene. The residue was purified by RP-HPLC to obtain 19 mg N-(5-Isopropyl-[1,3,4]thiadiazol-2-yl)-4-[2-(4-methoxy-phenyl)-oxazol-4-ylmethoxy]-benzenesulfonamide.

Workup

  1. customThe pyridine was removed in vacuo
  2. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-f4c67bcde69443aa9b5349e312d323ce
Source dataset
uspto-grants-2011_03
Patent number
US07910612B2

Reaction notes

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