Dimethylformamide → HCID 57633767, Verbindung

HRID 2240886Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240886
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:16][C:17]([F:20])([F:19])[F:18])[CH2:10][CH:11]([CH3:15])[C:12]([OH:14])=O)=[CH:5][C:4]=1[C:21]([F:24])([F:23])[F:22])#[N:2].C(Cl)(=O)C(Cl)=O.C[N:32](C=O)C.[NH4+].[OH-]>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:16][C:17]([F:20])([F:19])[F:18])[CH2:10][CH:11]([CH3:15])[C:12]([NH2:32])=[O:14])=[CH:5][C:4]=1[C:21]([F:23])([F:24])[F:22])#[N:2]

Komponenten

6

Edukt 4

HCID 6228Dimethylformamide2×HCID 14923Ammonium HydroxideHCID 65578Oxalyl chloride2×HCID 57633744HCID 57633744, Verbindung

Produkt 1

HCID 57633767HCID 57633767, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
42 °C

Versuchsvorschrift

To an ice-cold solution of 3-[[4-cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]-2-methylpropanoic acid (0.050 g, 0.14 mmol) in CH2Cl2 (3 mL), under nitrogen was added oxalyl chloride (0.023 g, 0.18 mmol) and DMF (cat) and the mixture was heated at 42° C. for 30 min. Upon cooling, additional oxalyl chloride (0.014 g, 0.11 mmol) and DMF (cat.) were added and heated for 30 min. Upon cooling, NH4OH (30% aqueous solution, 5 mL) was added and the mixture stirred at rt. After 1 h, the mixture was partitioned between CH2Cl2 and water. The organic phase was washed with 0.1N HCl and brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (1-5% MeOH—CH2Cl2 gradient) to give the title compound (0.044 g, 88% yield): 1H NMR (400 MHz, CDCl3) δ 7.58 (d, J=8.6 Hz, 1H), 7.01 (d, J=2.6 Hz, 1H), 6.89 (dd, J=8.6, 2.6 Hz, 1H), 5.70 (bs, NH), 5.54 (bs, NH), 4.22-4.08 (m, 2H), 3.85 (dd, J=15.4, 10.3 Hz, 1H), 3.54 (dd, J=15.4, 3.7 Hz, 1H), 2.80-2.70 (m, 1H), 1.23 (d, J=7.0 Hz, 3H).

Aufarbeitung

  1. temperatureUpon cooling
  2. temperatureheated for 30 min
  3. temperatureUpon cooling
  4. customthe mixture was partitioned between CH2Cl2 and water
  5. washThe organic phase was washed with 0.1N HCl and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (1-5% MeOH—CH2Cl2 gradient)

Quellen und Nachweise

ORD-Eintrag
ord-86cd01b9ece6482ea5036e32d26c4acb
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723385B2

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