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

반응식

HRID 734143 반응식
[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

참가 물질

7

반응물 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

생성물 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]pyridine수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d49e229dc3a843e79e87d43310e67cbe
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589202B2

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