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Pyrazole → 5-(2-Chloro-4-(1H-pyrazol-1-yl)phenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine

HRID 579340
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 579340
C([O-])([O-])=O.[Cs+].[Cs+].[Cl:7][C:8]1[CH:13]=[C:12](F)[CH:11]=[CH:10][C:9]=1[C:15]1[S:19][C:18]([N:20]([CH3:31])[CH:21]2[CH2:26][C:25]([CH3:28])([CH3:27])[NH:24][C:23]([CH3:30])([CH3:29])[CH2:22]2)=[N:17][N:16]=1.[NH:32]1[CH:36]=[CH:35][CH:34]=[N:33]1>CN(C=O)C.C(Cl)Cl>[Cl:7][C:8]1[CH:13]=[C:12]([N:32]2[CH:36]=[CH:35][CH:34]=[N:33]2)[CH:11]=[CH:10][C:9]=1[C:15]1[S:19][C:18]([N:20]([CH3:31])[CH:21]2[CH2:26][C:25]([CH3:28])([CH3:27])[NH:24][C:23]([CH3:30])([CH3:29])[CH2:22]2)=[N:17][N:16]=1
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Komponenten

6

Edukt 3

HCID 1048PyrazoleHCID 10796Cesium carbonateHCID 867271615-(2-Chloro-4-fluorophenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine

Produkt 1

HCID 867271625-(2-Chloro-4-(1H-pyrazol-1-yl)phenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Cs2CO3 (128 mg, 0.392 mmol) was added to a stirred solution of 5-(2-chloro-4-fluorophenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,4-thiadiazol-2-amine (50 mg, 0.131 mmol) and 1H-pyrazole (13 mg, 0.196 mmol) in DMF (1.3 mL). The reaction mixture was stirred at room temperature for 4 days then warmed to 60° C. and stirred for an additional 18 hours. The reaction mixture was diluted with DCM (10 mL), filtered through celite, and the DCM was removed in vacuo to afford the crude product as a pale brown liquid. The crude material was purified by UV directed preparative HPLC under acidic conditions (formic acid modified), collecting at 324 nm. The product containing fractions were combined and loaded onto a 1 g SCX cartridge (pre-wet with MeOH). The cartridge was washed with MeOH (10 mL) then flushed with 10% DCM in [7M NH3 in MeOH] (10 mL). The DCM/MeOH/NH3 was removed in vacuo to afford the title compound as a clear glass-like solid (37 mg, 66% yield). LC-MS: Rt 0.97 min; MS m/z 431.5 [M+H]+ [Method A]. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.67 (d, J=2.53 Hz, 1H), 8.14 (dd, J=5.56, 3.03 Hz, 2H), 7.97-8.02 (m, 1H), 7.83 (d, J=1.52 Hz, 1H), 6.64-6.60 (m, 1H), 4.37 (tt, J=12.25, 3.16 Hz, 1H), 3.02 (s, 3H), 1.63 (dd, J=12.13, 3.03 Hz, 2H), 1.45 (t, J=12.13 Hz, 2H), 1.21 (s, 6H), 1.09 (s, 6H).

Aufarbeitung

  1. temperaturethen warmed to 60° C.
  2. stirringstirred for an additional 18 hours
  3. filtrationfiltered through celite
  4. customthe DCM was removed in vacuo
  5. customto afford the crude product as a pale brown liquid
  6. customThe crude material was purified by UV
  7. customcollecting at 324 nm
  8. additionThe product containing fractions
  9. washThe cartridge was washed with MeOH (10 mL)
  10. customthen flushed with 10% DCM in [7M NH3 in MeOH] (10 mL)
  11. customThe DCM/MeOH/NH3 was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0a8ae9e319c647ec9cdccf2e7d1fd3d9
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09040712B2

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