Acetic Acid → 1-{3-[4-(1,1-Dioxo-1H-1lambda6-benzo[d]isothiazol-3-yl)-piperazin-1-yl]-propyl}-5-methanesulfonyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine

HRID 734143

Reaktionsgleichung

Reaktionsgleichung von HRID 734143
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][C:8]2[N:11]([CH2:24][CH2:25][CH:26]=O)[N:12]=[C:13]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[C:7]=2[CH2:6]1)(=[O:4])=[O:3].[N:28]1([C:34]2[C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=3[S:36](=[O:44])(=[O:43])[N:35]=2)[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:44]=[S:36]1(=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[C:34]([N:28]2[CH2:33][CH2:32][N:31]([CH2:26][CH2:25][CH2:24][N:11]3[C:8]4[CH2:9][CH2:10][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:6][C:7]=4[C:13]([C:14]4[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=4)=[N:12]3)[CH2:30][CH2:29]2)=[N:35]1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 6957183-(Piperazin-1-yl)-1,2-benzothiazole-1,1-dioneHCID 5049666Sodium triacetoxyborohydrideHCID 222938973-[5-Methanesulfonyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-propionaldehyde

Produkt 1

HCID 102330481-{3-[4-(1,1-Dioxo-1H-1lambda6-benzo[d]isothiazol-3-yl)-piperazin-1-yl]-propyl}-5-methanesulfonyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-[5-methanesulfonyl-3-(4-trifluoromethyl-phenyl) -4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-propionaldehyde (0.040 g, 0.13 mmol) and 3-piperazin-1-yl-benzo[d]isothiazole 1,1-dioxide (0.050 g, 0.21 mmol) in CH2Cl2 (0.5 mL), glacial AcOH (12 μL, 0.21 mmol) was added and stirred for 15 min at room temperature. NaBH(OAc)3 (0.058 g, 0.27 mmol) was added and stirred under nitrogen overnight. Saturated NaHCO3 (0.5 mL) was then added and stirred for 15 min. The layers separated and the aqueous layer was extracted with CH2Cl2 (0.5 mL). MPLC (silica, 2-15% MeOH/CH2Cl2) afforded the desired product as a white solid (0.048 g, 76%). TLC (silica, 12% MeOH/CH2Cl2): Rf=0.50. MS (electrospray): exact mass calculated for C28H31F3N6O4S2, 636.18; m/z found, 637.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.94 (dd, J=0.8, 7.6 Hz, 1H), 7.86 (d, J=7.8 Hz, 1H), 7.75 (d, J=8.3 Hz, 2H), 7.73-7.63 (m, 2H), 7.68 (d, J=8.3 Hz, 2H), 4.57 (s, 2H), 4.17 (t, J=6.9 Hz, 2H), 4.04 (br s, 4H), 3.69 (t, J=5.7 Hz, 2H), 2.94 (s, 3H), 2.92 (t, J=6.2 Hz, 2H), 2.62 (t, J=5.0 Hz, 4H), 2.44 (t, J=6.6 Hz, 2H), 2.13 (q, J=6.6 Hz, 2H).

Aufarbeitung

  1. stirringstirred under nitrogen overnight
  2. stirringstirred for 15 min
  3. customThe layers separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (0.5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-d49e229dc3a843e79e87d43310e67cbe
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589202B2

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