Trifluoroacetic acid → 1-(4-Chloro-2-(cyanomethoxy)phenyl)-N-(thiazol-2-YL)isoquinoline-6-sulfonamide 2,2,2-trifluoroacetate

HRID 1473589Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1473589
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([N:21](CC4C=CC(OC)=CC=4)[C:22]4[S:23][CH:24]=[CH:25][N:26]=4)(=[O:20])=[O:19])=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[C:4]([O:36][CH2:37][C:38]#[N:39])[CH:3]=1.[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41]>C(Cl)Cl>[F:43][C:42]([F:45])([F:44])[C:40]([OH:46])=[O:41].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([S:18]([NH:21][C:22]4[S:23][CH:24]=[CH:25][N:26]=4)(=[O:19])=[O:20])=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[C:4]([O:36][CH2:37][C:38]#[N:39])[CH:3]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 866876501-(4-Chloro-2-(cyanomethoxy)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-YL)isoquinoline-6-sulfonamide

Produkt 1

HCID 866876511-(4-Chloro-2-(cyanomethoxy)phenyl)-N-(thiazol-2-YL)isoquinoline-6-sulfonamide 2,2,2-trifluoroacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the light brown crude oil from Step 2 was added DCM (3 ml) and TFA (1 ml) and the mixture stirred at room temperature for 30 min affording PMB deprotection. The mixture was dried under reduced pressure and purified using basic, then acidic conditions, respectively affording product (16 mg, 16%). 1H NMR (400 MHz, DMSO-d6) δ=12.91 (br. s., 1H), 8.69 (d, J=5.8 Hz, 1H), 8.56 (d, J=1.9 Hz, 1H), 8.14 (d, J=5.2 Hz, 1H), 7.86 (dd, J=1.9, 8.9 Hz, 1H), 7.71 (d, J=8.9 Hz, 1H), 7.54 (d, J=1.9 Hz, 1H), 7.45 (d, J=8.1 Hz, 1H), 7.34 (dd, J=1.9, 8.1 Hz, 1H), 7.28 (d, J=4.6 Hz, 1H), 6.87 (d, J=4.6 Hz, 1H), 5.16 (d, J=1.0 Hz, 2H). m/z (ESI) 457.0 (M+H)+

Aufarbeitung

  1. customaffording PMB deprotection
  2. customThe mixture was dried under reduced pressure
  3. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-6a577c850259473eb90bbb4f02a2c1e8
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012443B2

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