Oxalyl chloride → 3-Chloro-6-(pivalamidomethyl)-N-(1-(3-(trifluoromethyl)phenoxy)isoquinolin-5-yl)picolinamide

HRID 1469801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469801
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][C:7]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=2[CH:10]=[CH:9][N:8]=1.[Cl:23][C:24]1[C:25]([C:38](O)=[O:39])=[N:26][C:27]([CH2:30][NH:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:28][CH:29]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[Cl:23][C:24]1[C:25]([C:38]([NH:17][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:11]=2[CH:10]=[CH:9][N:8]=[C:7]3[O:6][C:5]2[CH:18]=[CH:19][CH:20]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:4]=2)=[O:39])=[N:26][C:27]([CH2:30][NH:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:34])[CH3:35])=[CH:28][CH:29]=1

Komponenten

7

Edukt 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 716780491-(3-(Trifluoromethyl)phenoxy)isoquinolin-5-amineHCID 866922263-Chloro-6-(pivalamidomethyl)picolinic acid

Produkt 1

HCID 716785453-Chloro-6-(pivalamidomethyl)-N-(1-(3-(trifluoromethyl)phenoxy)isoquinolin-5-yl)picolinamideAusbeute 10,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The title compound was prepared following the procedure described in Example-1 using 1-(3-(trifluoromethyl)phenoxy)isoquinolin-5-amine (Intermediate-6, 100 mg, 0.329 mmol), 3-chloro-6-(pivalamidomethyl)picolinic acid (Intermediate-3, 126 mg, 0.46 mmol), oxalyl chloride (87 mg, 0.69 mmol), DMF (1 drop) and DIPEA (129 mg, 1.00 mmol) in CH2Cl2 (5 mL) to afford 20 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.89 (s, 1H), 8.34-8.30 (m, 2H), 8.17 (d, J=7.5 Hz, 1H), 8.09 (d, J=8.4 Hz, 1H), 8.00 (d, J=6.3 Hz, 1H), 7.83-7.78 (t, J=7.8 Hz, 1H), 7.73-7.67 (m, 5H), 7.40 (d, J=8.7 Hz, 1H), 4.45 (d, J=6.0 Hz, 2H), 1.17 (s, 9H); MS [M+H]+: 557.18.

Aufarbeitung

  1. customThe title compound was prepared

Quellen und Nachweise

ORD-Eintrag
ord-5e337ce6274b43db963b511be4b3545d
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006257B2

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