1,2-Dichloroethane → N-(2-hydroxyethyl)-6-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinamide

HRID 58108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58108
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][C:3]=1[C:11]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]2[C:12]=1[CH:13]=[N:14][NH:15]2.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[NH2:38][CH2:39][CH2:40][OH:41].C(N(C(C)C)C(C)C)C>CN(C=O)C.CCOC(C)=O>[OH:41][CH2:40][CH2:39][NH:38][C:8](=[O:10])[C:6]1[CH:5]=[CH:4][C:3]([C:11]2[CH:19]=[C:18]([C:20]([F:23])([F:21])[F:22])[CH:17]=[C:16]3[C:12]=2[CH:13]=[N:14][NH:15]3)=[C:2]([CH3:1])[N:7]=1

Komponenten

8

Edukt 5

HCID 111,2-DichloroethaneHCID 700EthanolamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 897833556-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinic acid

Produkt 1

HCID 89782824N-(2-hydroxyethyl)-6-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinamideAusbeute 36,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 6-methyl-5-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinic acid (1.6 g, 4.98 mmol) in DMF (20 mL) were added HOBt (0.942 g, 6.97 mmol), EDC (1.432 g, 7.47 mmol), 2-aminoethanol (0.913 g, 14.94 mmol), followed by N-ethyl-N-isopropylpropan-2-amine (4.34 mL, 24.90 mmol). The reaction mixture was stirred for 16 hours at room temperature, was subsequently diluted with EtOAc and was washed with brine. Volatiles were evaporated from the organic phase and the residue was purified by CombiFlash® chromatography, eluting with a gradient of 0-20% MeOH in DCM. The product-containing fractions were combined and concentrated in vacuo to give the title compound as a white solid (0.658 g, 36.3%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.43 (s, 3H), 3.44 (q, J=5.98 Hz, 2H), 3.57 (t, J=5.94 Hz, 2H), 7.38-7.44 (m, 1H), 7.90-8.07 (m, 4H), 8.70 (t, J=5.81 Hz, 1H); ESI-MS m/z [M+H]+ calc'd for C17H15F3N4O2, 365.1. found 365.2.

Aufarbeitung

  1. washwas washed with brine
  2. customVolatiles were evaporated from the organic phase
  3. customthe residue was purified by CombiFlash® chromatography
  4. washeluting with a gradient of 0-20% MeOH in DCM
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d8e84ccb75fa4262a6068ee19592e58f
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434743B2

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