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

HRID 473100Notes

Reaction equation

HRID 473100 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6](Cl)(=[O:8])=[O:7].[NH2:10][CH:11]1[C:19]2[C:14](=[CH:15][C:16]([CH2:20][C:21]3[CH:22]=[C:23]([CH2:31][OH:32])[CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=3)=[CH:17][CH:18]=2)[CH2:13][CH2:12]1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:32][CH2:31][C:23]1[CH:22]=[C:21]([CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=1)[CH2:20][C:16]1[CH:15]=[C:14]2[C:19](=[CH:18][CH:17]=1)[CH:11]([NH:10][S:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:8])=[O:7])[CH2:12][CH2:13]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 66734486(3-((1-amino-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)phenyl)methanol

Product 1

HCID 70222834N-(5-(3-(hydroxymethyl)-5-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-1-yl)thiophene-2-sulfonamideYield 35.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-thiophenesulfonyl chloride (23 mg, 0.126 mmol) was added to a solution of (3-((1-amino-2,3-dihydro-1H-inden-5-yl)methyl)-5-(trifluoromethyl)phenyl)methanol (40 mg, 0.124 mmol) and triethylamine (34 μL, 0.244 mmol) in DCM (2 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 the title compound (20.8 mg, 35.7%). MS (ESI): m/z [M−H]− 466.0.

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-0047234ba91b4591bc49743de839244c
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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