N-(4-(2-Amino-1,3-thiazol-4-yl)phenyl)acetamide → N-(4-(4-acetamidophenyl)thiazol-2-yl)-4-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)benzamide

HRID 1397901

Reaktionsgleichung

Reaktionsgleichung von HRID 1397901
[N:1]1([S:11]([C:14]2[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[NH2:23][C:24]1[S:25][CH:26]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([NH:35][C:36](=[O:38])[CH3:37])=[CH:31][CH:30]=2)[N:28]=1>>[C:36]([NH:35][C:32]1[CH:33]=[CH:34][C:29]([C:27]2[N:28]=[C:24]([NH:23][C:18](=[O:19])[C:17]3[CH:21]=[CH:22][C:14]([S:11]([N:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH2:4][CH2:3][CH2:2]4)(=[O:12])=[O:13])=[CH:15][CH:16]=3)[S:25][CH:26]=2)=[CH:30][CH:31]=1)(=[O:38])[CH3:37]

Komponenten

3

Edukt 2

HCID 519881N-(4-(2-Amino-1,3-thiazol-4-yl)phenyl)acetamideHCID 23189394-(1,2,3,4-Tetrahydroquinoline-1-sulfonyl)benzoic acid

Produkt 1

HCID 46912679N-(4-(4-acetamidophenyl)thiazol-2-yl)-4-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)benzamide

Versuchsvorschrift

4-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)benzoic acid (1) (100 mg, 0.32 mmol) was treated with N-(4-(2-aminothiazol-4-yl)phenyl)acetamide (57 mg, 0.24 mmol) using method B. The residue was purified using flash chromatography eluting with 0-60% EtOAc in hexanes to give N-(4-(4-acetamidophenyl)thiazol-2-yl)-4-(3,4-dihydroquinolin-1(2H)-ylsulfonyl)benzamide as a white solid. Yield: 28 mg (22%). 1H-NMR: 10.02 (s, 1H), 8.20 (d, J=8.5 Hz, 2H), 7.86 (d, J=8.5 Hz, 2H), 7.75 (d, J=8.5 Hz, 2H), 7.67-7.58 (m, 4H), 7.24-7.18 (m, 1H), 7.14-7.08 (m, 2H), 3.84-3.80 (m, 2H), 2.45 (t, J=7.0 Hz, 2H), 2.06 (s, 3H), 1.66-1.59 (m, 2H).

Aufarbeitung

  1. customThe residue was purified
  2. washeluting with 0-60% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e35d2b23e4de4d2c820f901b24ce7565
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901306B2

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