Potassium Carbonate → Ethyl 1-((1-(1-methylethylsulfonamido)-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

HRID 43032Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 43032
Cl[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([NH:12][S:13]([CH:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])[CH2:7][CH2:6]2.[F:19][C:20]([F:32])([F:31])[C:21]1[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:24][NH:23][N:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:17][CH:16]([S:13]([NH:12][CH:8]1[C:9]2[C:5](=[CH:4][C:3]([CH2:2][N:23]3[CH:24]=[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:21]([C:20]([F:19])([F:31])[F:32])=[N:22]3)=[CH:11][CH:10]=2)[CH2:6][CH2:7]1)(=[O:15])=[O:14])[CH3:18]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 67088048N-(5-(chloromethyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamideHCID 178469923HCID 178469923, Verbindung

Produkt 1

HCID 67088245Ethyl 1-((1-(1-methylethylsulfonamido)-2,3-dihydro-1H-inden-5-yl)methyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylateAusbeute 52,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To N-(5-(chloromethyl)-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide (0.250 mmol, 72 mg) in DMF (4 mL) was added ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate (0.250 mmol, 52.1 mg) and Potassium carbonate (0.750 mmol, 104 mg). The resultant solution was heated to 60° C. with stirring. After 1.5 h the reaction mixture was concentrated to remove DMF before partitioning between EtOAc/H2O and the phases mixed and separated. The organic layer was washed with water (×4) and brine before drying and concentration to a yellow oil. Purification on 10 g Si eluting with 1% MeOH/DCM gave the desired compound as an off-white solid (60 mg, 0.131 mmol, 52.2%). 1H NMR (400 MHz, CDCl3) δ 1.33 (t, 3H) 1.44 (d, 6H) 1.95 (m, 1H) 2.65 (m, 1H) 2.85 (m, 1H) 3.00 (m, 1H) 3.25 (m, 1H) 4.15 (d, 1H) 4.29 (q, 2H) 4.95 (m, 1H) 5.30 (s, 2H) 7.14 (s, 1H) 7.18 (d, 1H) 7.48 (d, 1H) 7.88 (s, 1H).

Aufarbeitung

  1. concentrationAfter 1.5 h the reaction mixture was concentrated
  2. customto remove DMF
  3. custombefore partitioning between EtOAc/H2O
  4. additionthe phases mixed
  5. customseparated
  6. washThe organic layer was washed with water (×4) and brine
  7. custombefore drying
  8. concentrationconcentration to a yellow oil
  9. customPurification on 10 g Si eluting with 1% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-906e5a7fdc734782b1a978506e01bb09
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536214B2

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