Triethylamine → 2,2,2-trifluoro-N-(5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-1-yl)acetamide

HRID 473101Notes

Reaction equation

HRID 473101 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3](OC1C(F)=C(F)C(F)=C(F)C=1F)=[O:4].[NH2:19][CH:20]1[C:28]2[C:23](=[CH:24][C:25]([CH2:29][C:30]3[CH:31]=[C:32]([CH2:40][OH:41])[CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=3)=[CH:26][CH:27]=2)[CH2:22][CH2:21]1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]([F:18])([F:17])[C:3]([NH:19][CH:20]1[C:28]2[C:23](=[CH:24][C:25]([CH2:29][C:30]3[CH:35]=[C:34]([C:36]([F:37])([F:38])[F:39])[CH:33]=[C:32]([CH2:40][OH:41])[CH:31]=3)=[CH:26][CH:27]=2)[CH2:22][CH2:21]1)=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 66734486(3-((1-amino-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)phenyl)methanol

Product 1

HCID 866687492,2,2-trifluoro-N-(5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-1-yl)acetamideYield 27.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pentafluorophenyl trifluoroacetate (28 mg, 0.1 mmol) was added to a solution of (3-((1-amino-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)phenyl)methanol (30 mg, 0.093 mmol) and triethylamine (26 μL, 0.187) in DCM (1 mL). The reaction was stirred at rt for 24 h before aq. sat. NaHCO3 (2 mL) was added to the mixture and the whole was filtered over a phase separator. The organic filtrate was evaporated to dryness in a Genevac. The crude material was purified by prep. LCMS to afford LEBE27-031-2 the title compound (10.3 mg, 27.7%). MS (ESI): m/z [M−H]− 416.0

Workup

  1. additionwas added to the mixture
  2. filtrationthe whole was filtered over a phase separator
  3. customThe organic filtrate was evaporated to dryness in a Genevac
  4. customThe crude material was purified by prep

Sources & evidence

ORD record
ord-532505facd0640de8c1be978d7539527
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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