Hydrochloric Acid → tert-Butyl 2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1-benzofuran-6-carboxylate

HRID 339111

Reaction equation

HRID 339111 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:19]=[CH:18][C:11]2[CH:12]=[C:13]([C:15]([OH:17])=O)[O:14][C:10]=2[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:20][C:21]([F:35])([F:34])[CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1)[NH2:23].O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.Cl>CN(C)C=O>[F:20][C:21]([F:34])([F:35])[CH:22]([NH:23][C:15]([C:13]1[O:14][C:10]2[CH:9]=[C:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:19]=[CH:18][C:11]=2[CH:12]=1)=[O:17])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:32])([F:33])[F:31])[CH:25]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 438251722,2,2-Trifluoro-1-(3-(trifluoromethyl)phenyl)ethanamineHCID 582479766-(tert-Butoxycarbonyl)-1-benzofuran-2-carboxylic acid

Product 1

HCID 58247936tert-Butyl 2-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}carbamoyl)-1-benzofuran-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 6-(tert-butoxycarbonyl)-1-benzofuran-2-carboxylic acid (350 mg, 1.33 mmol) and 2,2,2-trifluoro-1-[3-trifluoromethylphenyl]ethanamine (357 mg, 1.46 mmol) in N,N-dimethylformamide (5 ml) was admixed with 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (304 mg, 1.46 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. This leaves 453 mg as a mixture of the tert-butyl ester and of the free acid, which was used for the next step without further purification.

Workup

  1. customThe cooled reaction solution
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with sat. sodium hydrogencarbonate solution and saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. additionThis leaves 453 mg as a mixture of the tert-butyl ester
  8. customof the free acid, which was used for the next step without further purification

Sources & evidence

ORD record
ord-1fe95d17e6f14f408ace0eabd2277447
Source dataset
uspto-grants-2014_11
Patent number
US08889878B2

Linked notes

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