Triethylamine → 4-chloro-3-methoxy-N-(4-methyl-1,2,5-oxadiazol-3-yl)-2,3-dihydro-1-benzothiophene-5-carboxamide 1,1-dioxide

HRID 575915Notes

Reaction equation

HRID 575915 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]([O:13][CH3:14])[CH2:9][S:10](=[O:12])(=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]([OH:17])=O.[CH3:18][C:19]1[C:20]([NH2:24])=[N:21][O:22][N:23]=1.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[C:7]2[CH:8]([O:13][CH3:14])[CH2:9][S:10](=[O:11])(=[O:12])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]([NH:24][C:20]1[C:19]([CH3:18])=[N:23][O:22][N:21]=1)=[O:17]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 286743-Amino-4-methylfurazanHCID 111923Propylphosphonic anhydrideHCID 867154224-Chloro-3-methoxy-2,3-dihydro-1-benzothiophene-5-carboxylic acid 1,1-dioxide

Product 1

HCID 867154214-chloro-3-methoxy-N-(4-methyl-1,2,5-oxadiazol-3-yl)-2,3-dihydro-1-benzothiophene-5-carboxamide 1,1-dioxide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1.00 g (3.14 mmol) of 4-chloro-3-methoxy-2,3-dihydro-1-benzothiophene-5-carboxylic acid 1,1-dioxide and 0.33 g (3.15 mmol) of 4-methyl-1,2,5-oxadiazol-3-yl-amine were dissolved at room temperature (RT) in 35 ml of CH2Cl2, 3.02 g (4.74 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF) were added and the mixture was stirred at RT for 1 h. Subsequently, 2.18 ml (15.64 mmol) of triethylamine and 75 mg (0.61 mmol) of 4-dimethylaminopyridine (DMAP) were added and the whole mixture was stirred at RT for 16 h. This was followed by washing with water and twice with 6N hydrochloric acid, drying of the organic phase over Na2SO4 and filtration with suction through silica gel, washing through with 1:2 heptane/ethyl acetate and concentration. Yield 708 mg (63%).

Workup

  1. stirringthe whole mixture was stirred at RT for 16 h
  2. washby washing with water and twice with 6N hydrochloric acid
  3. dry with materialdrying of the organic phase over Na2SO4 and filtration with suction through silica gel
  4. washwashing through with 1:2 heptane/ethyl acetate and concentration

Sources & evidence

ORD record
ord-17834b21d09d441f81d075bdb2ca113d
Source dataset
uspto-grants-2015_05
Patent number
US09035067B2

Reaction notes

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