1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-methyl-N-(thietan-3-yl)-4-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzamide

HRID 1692567Notes

Reaction equation

HRID 1692567 reaction equation
Br.[S:2]1[CH2:5][CH:4]([NH2:6])[CH2:3]1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH3:30][C:31]1[CH:39]=[C:38]([C:40]2[CH2:41][C:42]([C:49]3[CH:54]=[C:53]([Cl:55])[C:52]([Cl:56])=[C:51]([Cl:57])[CH:50]=3)([C:45]([F:48])([F:47])[F:46])[CH2:43][N:44]=2)[CH:37]=[CH:36][C:32]=1[C:33](O)=[O:34]>CN(C)C=O.C(N(CC)CC)C.C(OC)(C)(C)C>[CH3:30][C:31]1[CH:39]=[C:38]([C:40]2[CH2:41][C:42]([C:49]3[CH:50]=[C:51]([Cl:57])[C:52]([Cl:56])=[C:53]([Cl:55])[CH:54]=3)([C:45]([F:46])([F:48])[F:47])[CH2:43][N:44]=2)[CH:37]=[CH:36][C:32]=1[C:33]([NH:6][CH:4]1[CH2:5][S:2][CH2:3]1)=[O:34]

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 53346555Thietan-3-amine hydrobromideHCID 582709962-methyl-4-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzoic acid

Product 1

HCID 582709782-methyl-N-(thietan-3-yl)-4-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzamide

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of thietan-3-amine hydrobromide in N,N-dimethylformamide, triethylamine was added at 0° C. Then 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (122 mg, 0.53 mmol), 1-hydroxybenzotriazole monohydrate (72 mg, 0.53 mmol), and 2-methyl-4-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]benzoic acid (200 mg, 0.44 mmol) were added to the solution. The reaction mixture was stirred overnight at room temperature and then diluted with t-BuOMe and washed with 2M HCl, and after that with H2O, saturated NaCl aq. and dried over MgSO4. After evaporation, the residue was purified with chromatography (220 mg, 95%).

Workup

  1. washwashed with 2M HCl
  2. dry with materialafter that with H2O, saturated NaCl aq. and dried over MgSO4
  3. customAfter evaporation
  4. customthe residue was purified with chromatography (220 mg, 95%)

Sources & evidence

ORD record
ord-39f0117e67a04a6f83a0d669e224091a
Source dataset
uspto-grants-2012_04
Patent number
US08158560B2

Reaction notes

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