1-Hydroxybenzotriazole → N-[2-(Trifluoromethyl)benzyl]-5-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-2,3-dihydro-1-benzofuran-7-carboxamide

HRID 1505765Notes

Reaction equation

HRID 1505765 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([NH:11][C:12]1[CH:13]=[C:14]([C:21]([OH:23])=O)[C:15]2[O:19][CH2:18][CH2:17][C:16]=2[CH:20]=1)=[O:10].Cl.C(C(NCCCN(C)C)=N)C.ON1C2C=CC=CC=2N=N1.[F:48][C:49]([F:59])([F:58])[C:50]1[CH:57]=[CH:56][CH:55]=[CH:54][C:51]=1[CH2:52][NH2:53]>CN(C=O)C.C(N(CC)CC)C>[F:48][C:49]([F:58])([F:59])[C:50]1[CH:57]=[CH:56][CH:55]=[CH:54][C:51]=1[CH2:52][NH:53][C:21]([C:14]1[C:15]2[O:19][CH2:18][CH2:17][C:16]=2[CH:20]=[C:12]([NH:11][C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:25])([F:24])[F:1])=[O:10])[CH:13]=1)=[O:23]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 764472-(Trifluoromethyl)benzylamineHCID 90229275HCID 90229275, compoundHCID 178458058HCID 178458058, compound

Product 1

HCID 71532088N-[2-(Trifluoromethyl)benzyl]-5-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-2,3-dihydro-1-benzofuran-7-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 5-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-2,3-dihydro-1-benzofuran-7-carboxylic acid (35 mg) in DMF (2 mL), N′-(ethylcarbonimidoyl)-N,N-dimethyl-1,3-propanediamine hydrochloride (23 mg), 1-hydroxybenzotriazol (23 mg) and triethylamine (17 μL) were added. Under ice-cooling, to the mixture was added 2-(trifluoromethyl)benzylamine (15 μL), and it was stirred at room temperature overnight. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The ethyl acetate layer was washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was washed with n-hexane/ethyl acetate (1:1) and collected by filtration to obtain the titled compound (43 mg) as colorless powder. MS (ESI+) m/z 509 (M+H)+, Rt=2.31 minutes (method A)

Workup

  1. temperatureUnder ice-cooling, to the mixture
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed sequentially with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. washThe residue was washed with n-hexane/ethyl acetate (1:1)
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e8ff3c10c01d4f92bd89a9a451a210e2
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

Loading…