Hydrochloric Acid → N-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl carbamothioyl)-2-(2-fluorophenyl)acetamide di-hydrochloride

HRID 1261363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1261363
[F:1][C:2]1[CH:3]=[C:4]([NH2:24])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[N:19]([CH3:23])[CH:20]=[CH:21][N:22]=3)[S:17][C:10]=12.[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][C:33]([N:35]=[C:36]=[S:37])=[O:34].[ClH:38]>C1COCC1.CO>[ClH:38].[ClH:38].[F:1][C:2]1[CH:3]=[C:4]([NH:24][C:36]([NH:35][C:33](=[O:34])[CH2:32][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[F:25])=[S:37])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[N:19]([CH3:23])[CH:20]=[CH:21][N:22]=3)[S:17][C:10]=12

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 167744322-(2-Fluorophenyl)acetyl isothiocyanateHCID 594244803-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine

Produkt 1

HCID 86604196N-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl carbamothioyl)-2-(2-fluorophenyl)acetamide di-hydrochlorideAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of aniline 219 (100 mg, 0.29 mmol, scheme 47) and 2-(2-fluorophenyl)acetyl isothiocyanate (115 mg, 0.58 mmol) in THF (3 mL) was stirred for 1 hour, loaded directly onto a column containing silica gel and eluted sequentially with EtOAc and EtOAc/MeOH (100:1), to produce a white solid. This material was suspended in MeOH (5 mL) and HCl (1.0M in ether, 1 mL) was added to form a clear solution that was evaporated to dryness. The residue was washed with ether, suspended in H2O, and lyophilized to afford the title compound (80 mg, 45% yield) as a yellowish solid. 1H-NMR (DMSO-d6) δ (ppm): 12.42(s, 1H), 11.88(s, 1H), 8.65(d. 1H, J=5.5 Hz), 8.20(s, 1H), 8.05(d, 1H, J=1.7 Hz), 7.74(s, 1H), 7.58-7.55(m, 3H) 7.39-7.32(m, 2H), 7.21-7.16(m, 2H), 6.82(d, 1H, J=5.5 Hz), 4.02(s, 3H), 3.93(s, 2H), MS (m/z): 536.2(M+H) (found).

Aufarbeitung

  1. additioncontaining silica gel
  2. washeluted sequentially with EtOAc and EtOAc/MeOH (100:1)
  3. customto produce a white solid
  4. customto form a clear solution that
  5. customwas evaporated to dryness
  6. washThe residue was washed with ether

Quellen und Nachweise

ORD-Eintrag
ord-f53004867e7b404ea31fb9d2d86bb624
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470850B2

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