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Trifluoroacetic acid → 1-(2-(1,2,3,6-tetrahydropyridin-4-yl)-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide

HRID 1473328
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Reaktionsgleichung

Reaktionsgleichung von HRID 1473328
COC1C=C(OC)C=CC=1C[N:6]([C:43]1[S:44][CH:45]=[CH:46][N:47]=1)[S:7]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[C:16]([C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:21]=1[C:30]1[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH:31]=1)=[N:15][CH:14]=[CH:13]2)(=[O:9])=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:33]1[CH2:32][CH:31]=[C:30]([C:21]2[CH:22]=[C:23]([C:26]([F:29])([F:28])[F:27])[CH:24]=[CH:25][C:20]=2[C:16]2[C:17]3[C:12](=[CH:11][C:10]([S:7]([NH:6][C:43]4[S:44][CH:45]=[CH:46][N:47]=4)(=[O:9])=[O:8])=[CH:19][CH:18]=3)[CH:13]=[CH:14][N:15]=2)[CH2:35][CH2:34]1
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4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86687380tert-butyl 4-(2-(6-(N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)isoquinolin-1-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Produkt 1

HCID 866873811-(2-(1,2,3,6-tetrahydropyridin-4-yl)-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344Dichloromethane
Lösungsmittel

Versuchsvorschrift

Tert-butyl 4-(2-(6-(N-(2,4-dimethoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)isoquinolin-1-yl)-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate (0.073 g, 0.095 mmol) was dissolved in 1 mL of DCM and TFA (0.073 ml, 0.948 mmol) was added. The reaction was stirred overnight at room temperature. The solution was concentrated and concentrated from DCM two more times. The resulting yellow solid was triturated with diethyl ether and stirred for 15 minutes. The solution was filtered and the solids were washed with diethyl ether. The material was dissolved in methanol and loaded onto an SCX ion exchange column (pre-wetted with methanol) (Biotage AB, Uppsala, SE). The column was washed several times with methanol, then the product was liberated with 2.0 M ammonia/methanol solution. The filtrate was concentrated to afford 1-(2-(1,2,3,6-tetrahydropyridin-4-yl)-4-(trifluoromethyl)phenyl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ=8.60 (d, J=5.7 Hz, 1H), 8.44 (d, J=1.5 Hz, 1H), 8.05 (d, J=5.4 Hz, 1H), 7.93-7.79 (m, 2H), 7.72 (s, 1H), 7.61 (dd, J=8.4, 16.3 Hz, 2H), 6.96 (d, J=3.9 Hz, 1H), 6.52 (d, J=3.9 Hz, 1H), 5.49 (br. s., 1H), 3.24 (br. s., 2H), 2.72 (t, J=5.8 Hz, 2H), 2.04 (br. s., 2H). m/z (ESI) 517.2 (M+H)+.

Aufarbeitung

  1. concentrationThe solution was concentrated
  2. concentrationconcentrated from DCM two more times
  3. customThe resulting yellow solid was triturated with diethyl ether
  4. stirringstirred for 15 minutes
  5. filtrationThe solution was filtered
  6. washthe solids were washed with diethyl ether
  7. dissolutionThe material was dissolved in methanol
  8. washThe column was washed several times with methanol
  9. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-5b5444aa01654943867316b31891908c
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09012443B2

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