Oxalyl chloride → 2-Chloro-5-(pivalamidomethyl)-N-(1-(3-(trifluoromethyl)phenoxy)isoquinolin-5-yl)benzamide

HRID 1469802Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469802
[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[CH:32]=[CH:31][C:30]([CH2:33][NH:34][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:29][C:25]=1[C:26](O)=[O:27].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[CH:32]=[CH:31][C:30]([CH2:33][NH:34][C:35](=[O:40])[C:36]([CH3:38])([CH3:37])[CH3:39])=[CH:29][C:25]=1[C:26]([NH:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[CH:10]=[CH:9][N:8]=[C:7]2[O:6][C:5]1[CH:18]=[CH:19][CH:20]=[C:3]([C:2]([F:1])([F:21])[F:22])[CH:4]=1)=[O:27]

Komponenten

7

Edukt 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 584832082-Chloro-5-[(2,2-dimethylpropanamido)methyl]benzoic acidHCID 716780491-(3-(Trifluoromethyl)phenoxy)isoquinolin-5-amine

Produkt 1

HCID 866922742-Chloro-5-(pivalamidomethyl)-N-(1-(3-(trifluoromethyl)phenoxy)isoquinolin-5-yl)benzamideAusbeute 16,9 %

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), 2-chloro-5-(pivalamidomethyl)benzoic acid (Intermediate-5, 133 mg, 0.493 mmol), oxalyl chloride (87 mg, 0.69 mmol), DMF (1 drop) and DIPEA (129 mg, 1.00 mmol) in CH2Cl2 (5 mL) to afford 31 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 10.76 (s, 1H), 8.32 (d, J=8.4 Hz, 1H), 8.22 (br t, 1H), 8.08 (d, J=7.2 Hz, 1H), 7.98 (d, J=5.7 Hz, 1H), 7.82-7.67 (m, 6H), 7.55 (m, 2H), 7.39 (d, 1H), 4.34-4.32 (d, J=5.7 Hz, 2H), 1.14 (s, 9H); MS [M+H]+: 556.16.

Aufarbeitung

  1. customThe title compound was prepared

Quellen und Nachweise

ORD-Eintrag
ord-5ca8ab0bbe73454894d18c673d94f348
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006257B2

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