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1-Hydroxybenzotriazole → (S)-N-((3-Fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)-5-methoxy-6-nitropicolinamide

HRID 509391
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Reaktionsgleichung

Reaktionsgleichung von HRID 509391
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:12]([OH:14])=O)=[N:7][C:8]=1[N+:9]([O-:11])=[O:10].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[F:47][C:48]1[CH:49]=[C:50]([C@@H:59]([C:61]2[C:66]([F:67])=[CH:65][CH:64]=[CH:63][N:62]=2)[NH2:60])[CH:51]=[CH:52][C:53]=1[O:54][C:55]([F:58])([F:57])[F:56]>CN(C=O)C.CCCCCC.O.CCOC(C)=O>[F:47][C:48]1[CH:49]=[C:50]([C@@H:59]([C:61]2[C:66]([F:67])=[CH:65][CH:64]=[CH:63][N:62]=2)[NH:60][C:12](=[O:14])[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:8]([N+:9]([O-:11])=[O:10])[N:7]=2)[CH:51]=[CH:52][C:53]=1[O:54][C:55]([F:58])([F:57])[F:56]
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Komponenten

10

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 225980405-Methoxy-6-nitropicolinic acidHCID 86687985(S)-(3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methanamine hydrochloride2×

Produkt 1

HCID 71144173
(S)-N-((3-Fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)-5-methoxy-6-nitropicolinamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-methoxy-6-nitropicolinic acid (200 mg, 0.001 mol) in DMF was added EDCI.HCl (231.6 mg, 0.0012 mol, Molekula, India) followed by HOBt (164.7 mg, 0.0012 mol, Spectrochem, India), DIPEA (521.87 mg, 0.0040 mol, Spectrochem, India) and (S)-(3-fluoro-4-(trifluoromethoxy) phenyl) (3-fluoropyridin-2-yl) methanamine hydrochloride (349.83 mg, 0.0010 mmol, Intermediate 6) at 0° C. The reaction mixture was stirred at room temperature overnight. After completion of the reaction (monitored by TLC, 50% EtOAc in hexane), water (20 mL) was added to the reaction mixture, and the aqueous solution was extracted with EtOAc (20 mL×2). The combined organic layers were washed with water (100 mL×2). The organic layer was dried and concentrated providing a residue which was purified by silica gel (60-120 mesh) column chromatography eluting with 40-50% EtOAc in petroleum ether to give the title compound as a solid. 1H-NMR (400 MHz, DMSO-d6): δ 9.46 (d, J=7.6 Hz, 1H), 8.53 (d, J=4.4 Hz, 1H), 8.34 (d, J=8.4 Hz, 1H), 8.12 (d, J=8.8 Hz, 1H), 7.83 (t, J=9.6 Hz, 1H), 7.58-7.55 (m, 3H), 7.35 (d, J=8.4 Hz, 1H), 6.57 (d, J=7.2 Hz, 1H), 4.04 (s, 3H). MS (ESI, positive ion) m/z: 485 (M+H).

Aufarbeitung

  1. additionwas added to the reaction mixture
  2. extractionthe aqueous solution was extracted with EtOAc (20 mL×2)
  3. washThe combined organic layers were washed with water (100 mL×2)
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customproviding a residue which
  7. customwas purified by silica gel (60-120 mesh) column chromatography
  8. washeluting with 40-50% EtOAc in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-3394a8b7018f40739d6083ab633426a4
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09096527B2

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