Cyclopropanemethanamine → 5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid cyclopropylmethyl-amide

HRID 572278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572278
[CH3:1][C:2]1[C:3]([C:11]2[S:15][C:14]([C:16]([OH:18])=O)=[CH:13][CH:12]=2)=[N:4][O:5][C:6]=1[C:7]([F:10])([F:9])[F:8].[CH:19]1([CH2:22][NH2:23])[CH2:21][CH2:20]1>>[CH:19]1([CH2:22][NH:23][C:16]([C:14]2[S:15][C:11]([C:3]3[C:2]([CH3:1])=[C:6]([C:7]([F:8])([F:9])[F:10])[O:5][N:4]=3)=[CH:12][CH:13]=2)=[O:18])[CH2:21][CH2:20]1

Komponenten

3

Edukt 2

HCID 75646CyclopropanemethanamineHCID 252109975-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid

Produkt 1

HCID 252110965-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid cyclopropylmethyl-amideAusbeute 67 %

Versuchsvorschrift

Prepared from 5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and cyclopropylmethylamine by the method described in Example 2 Method B. The reaction mixture was evaporated in vacuo, triturated and filtered with the aid of water, then washed with an aqueous 1 N hydrochloric acid solution followed by water. The crude solid was then triturated with a 25% EtOAc/hexanes solution (3×1 mL) and air dried to afford product as a colorless solid (110 mg, 67%). 1H NMR (CDCl3) 0.27-0.32 (m, 2H), 0.55-0.61 (m, 2H), 1.03-1.12 (m, 1H), 2.37 (d, J=0.9, 3H), 3.31 (d, J=5.7, 1H), 3.33 (d, J=5.7, 1H), 6.23 (br s, 1H), 7.50 (d, J=4.0, 1H), 7.56 (d, J=4.0, 1H). 19F NMR −63.1. LC/MS 6.5 min, [M+1]+ 331.

Aufarbeitung

  1. customThe reaction mixture was evaporated in vacuo
  2. customtriturated
  3. filtrationfiltered with the aid of water
  4. washwashed with an aqueous 1 N hydrochloric acid solution
  5. customThe crude solid was then triturated with a 25% EtOAc/hexanes solution (3×1 mL) and air
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-be7aeb6ee50444209b8cbc771ed8e22d
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029397B2

Notizen zur Reaktion

Wird geladen…