Hydrochloride methanol → 3-(5-(2,5-Difluorophenyl)-3-(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propan-1-amine

HRID 2040359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2040359
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:11]([C:12]2[S:13][C:14]3[CH2:15][N:16]([CH3:21])[CH2:17][CH2:18][C:19]=3[N:20]=2)[N:10]=[C:9]([C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[F:29])[S:8]1)=[N+]=[N-].Cl.CO>CO.[Pd]>[F:29][C:23]1[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:22]=1[C:9]1[S:8][C:7]([CH2:6][CH2:5][CH2:4][NH2:1])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:11]([C:12]2[S:13][C:14]3[CH2:15][N:16]([CH3:21])[CH2:17][CH2:18][C:19]=3[N:20]=2)[N:10]=1

Komponenten

5

Edukt 2

HCID 21893726Hydrochloride methanolHCID 866087732-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

Produkt 1

HCID 119599503-(5-(2,5-Difluorophenyl)-3-(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propan-1-amineAusbeute 61,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine (0.046 g, 0.090 mmol) in 2 mL of methanol was added 1N HCl/MeOH (0.27 mL, 0.27 mmol) followed by 10% Pd/C (10 mg). The mixture was hydrogenated under a balloon atmosphere for 1 hour then filtered through GF paper and the filtrate concentrated in vacuo. The residue was triturated with diethyl ether, filtered, washed with ether and dried in vacuo to afford the desired product as a bright yellow solid (0.027 g, 50%). MS ESI (+) m/z 486 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 7.59 (m, 1H), 7.45 (d, 2H, J=7.6 Hz), 7.32 (m, 2H), 7.26 (m, 1H), 7.06 (m, 2H), 3.50 (m, 2H), 3.43 (m, 1H), 2.77 (t, 2H, J=6.9 Hz), 2.68 (m, 2H), 2.56 (m, 2H), 2.46 (s, 3H), 2.41 (m, 1H), 1.99 (m, 1H), 1.55 (m, 1H) ppm.

Aufarbeitung

  1. filtrationthen filtered through GF paper
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was triturated with diethyl ether
  4. filtrationfiltered
  5. washwashed with ether
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7892dd332d7d4bd5ae24d9603e0314c8
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580828B2

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