Hydrochloric Acid → N'-Cyclopropyl-N2-(2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl)-1-benzofuran-2,6-dicarboxamide

HRID 2371069Notes

Reaction equation

HRID 2371069 reaction equation
[F:1][C:2]([F:30])([F:29])[CH:3]([NH:14][C:15]([C:17]1[O:18][C:19]2[CH:25]=[C:24]([C:26](O)=[O:27])[CH:23]=[CH:22][C:20]=2[CH:21]=1)=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[CH:50]1([NH2:53])[CH2:52][CH2:51]1.Cl>CN(C)C=O>[CH:50]1([NH:53][C:26]([C:24]2[CH:23]=[CH:22][C:20]3[CH:21]=[C:17]([C:15]([NH:14][CH:3]([C:4]4[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:12])([F:11])[F:13])[CH:5]=4)[C:2]([F:30])([F:1])[F:29])=[O:16])[O:18][C:19]=3[CH:25]=2)=[O:27])[CH2:52][CH2:51]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 69828CyclopropylamineHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 582479382-({2,2,2-Trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1-benzofuran-6-carboxylic acid

Product 1

HCID 58247948N'-Cyclopropyl-N2-(2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl)-1-benzofuran-2,6-dicarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-({2,2,2-trifluoro-1-[3-(trifluormethyl)phenyl]ethyl}carbamoyl)-1-benzofuran-6-carboxylic acid (100 mg, 0.21 mmol) in N,N-dimethylformamide (1 ml) was admixed with 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (100 mg, 0.46 mmol) and cyclopropylamine (36 mg, 0.63 mmol), and stirred in a closed vessel at 50° C. overnight. The cooled reaction solution was admixed with hydrochloric acid (1 M) and extracted with ethyl acetate. The organic phase was washed with sat, sodium hydrogencarbonate solution and saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure. The residue was chromatographed on a preparative HPLC with water/acetonitrile as the eluent (gradient=43 min from 10%, acetonitrile in water to 100% acetonitrile).

Workup

  1. customThe cooled reaction solution
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed
  4. dry with materialsodium hydrogencarbonate solution and saturated sodium chloride solution, dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue was chromatographed on a preparative HPLC with water/acetonitrile as the eluent (gradient=43 min from 10%, acetonitrile in water to 100% acetonitrile)

Sources & evidence

ORD record
ord-5a41eb776fbb4d6e866d4bbed58a86c3
Source dataset
uspto-grants-2014_04
Patent number
US08710242B2

Reaction notes

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