Triethylamine → 2-chloro-N-(5-ethyl-1,3,4-oxadiazol-2-yl)-4-(methylsulfonyl)benzamide

HRID 511741Notes

Reaction equation

HRID 511741 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]([OH:14])=O.[CH2:15]([C:17]1[O:21][C:20]([NH2:22])=[N:19][N:18]=1)[CH3:16].C(P1(=O)OP(=O)(CCC)OP(=O)(CCC)O1)CC.C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[C:12]([NH:22][C:20]1[O:21][C:17]([CH2:15][CH3:16])=[N:18][N:19]=1)=[O:14]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 3434875-Ethyl-1,3,4-oxadiazol-2-amineHCID 7358632-Chloro-4-(methylsulfonyl)benzoic acid

Product 1

HCID 683277192-chloro-N-(5-ethyl-1,3,4-oxadiazol-2-yl)-4-(methylsulfonyl)benzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

415 mg (1.77 mmol) of 2-chloro-4-(methylsulfonyl)benzenecarboxylic acid and 200 mg (1.77 mmol) of 5-ethyl-1,3,4-oxadiazol-2-amine are dissolved at RT in 9 ml of CH2Cl2. Then 1.68 g (2.64 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF) are added, the mixture is stirred at RT for one hour and then 0.246 ml (1.77 mmol) of triethylamine, 43 mg (0.35 mmol) of 4-dimethylaminopyridine are added. The reaction mixture is stirred at RT for 48 h and then washed twice with 4 ml each time of water, and purified by column chromatography (prep. HPLC; acetonitrile/water). Yield 41 mg (6%).

Workup

  1. stirringThe reaction mixture is stirred at RT for 48 h
  2. washwashed twice with 4 ml each time of water
  3. custompurified by column chromatography (prep. HPLC; acetonitrile/water)

Sources & evidence

ORD record
ord-51405c517d504c148b768f7e1aebb933
Source dataset
uspto-grants-2015_08
Patent number
US09101141B2

Reaction notes

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