Triethylamine → N-(thietan-3-yl)-4-[3-(3,4,5-trichlorophenyl)-3-(trifluoro-methyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-(trifluoromethyl)benzamide

HRID 1692566Notes

Reaction equation

HRID 1692566 reaction equation
Br.[S:2]1[CH2:5][CH:4]([NH2:6])[CH2:3]1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[Cl:37][C:38]1[CH:39]=[C:40]([C:46]2([C:64]([F:67])([F:66])[F:65])[CH2:50][C:49]([C:51]3[CH:59]=[CH:58][C:54]([C:55](O)=[O:56])=[C:53]([C:60]([F:63])([F:62])[F:61])[CH:52]=3)=[N:48][CH2:47]2)[CH:41]=[C:42]([Cl:45])[C:43]=1[Cl:44]>C(OC)(C)(C)C>[S:2]1[CH2:5][CH:4]([NH:6][C:55](=[O:56])[C:54]2[CH:58]=[CH:59][C:51]([C:49]3[CH2:50][C:46]([C:40]4[CH:39]=[C:38]([Cl:37])[C:43]([Cl:44])=[C:42]([Cl:45])[CH:41]=4)([C:64]([F:65])([F:66])[F:67])[CH2:47][N:48]=3)=[CH:52][C:53]=2[C:60]([F:63])([F:62])[F:61])[CH2:3]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 53346555Thietan-3-amine hydrobromideHCID 582709924-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-(trifluoromethyl)benzoic acid

Product 1

HCID 58271002N-(thietan-3-yl)-4-[3-(3,4,5-trichlorophenyl)-3-(trifluoro-methyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-(trifluoromethyl)benzamideYield 68.6%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To the solution of thietan-3-amine hydrobromide (40 mg, 0.23 mmol) in 1,2-dichloromethane was added triethylamine (60 mg, 0.59 mmol) at 0° C. After that 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (54 mg, 0.23 mmol), 1-hydroxybenzotriazole monohydrate (32 mg, 0.23 mmol), and 4-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-(trifluoromethyl)benzoic acid (100 mg, 0.19 mmol) were added to the solution at 0° C. Then the reaction mixture was stirred overnight at room temperature and diluted with t-butylmethylether, and washed with water, and dried over magnesium sulfate anhydrous. After evaporation, the residue was purified with silicagel column chromatography to give 75 mg of N-(thietan-3-yl)-4-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-(trifluoromethyl)benzamide.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate anhydrous
  3. customAfter evaporation
  4. customthe residue was purified with silicagel column chromatography

Sources & evidence

ORD record
ord-31b10f3f257445c5a45883ce9b177faf
Source dataset
uspto-grants-2012_04
Patent number
US08158560B2

Reaction notes

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