Ammonium Hydroxide → 2-(4-(4-((6-Aminopyridazin-3-yl)sulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol

HRID 1972534노트

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HRID 1972534 반응식
Cl[C:2]1[N:7]=[N:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[NH4+:34]>CCO>[NH2:34][C:2]1[N:7]=[N:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 14923Ammonium HydroxideHCID 569326312-(4-(4-((6-Chloropyridazin-3-yl)sulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol

생성물 1

HCID 866703892-(4-(4-((6-Aminopyridazin-3-yl)sulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol수율 60.3%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
110 °C

실험 절차

To a 2 mL microwave vial was added 2-(4-(4-((6-chloropyridazin-3-yl)sulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (50 mg, 0.099 mmol), EtOH (1.0 mL) and ammonium hydroxide (2.0 mL, 51 mmol). The solution was heated in an Emrys Optimizer microwave reactor (Personal Chemistry, Biotage AB, Inc., Uppsala, Sweden) at 110° C. for 1 h and then concentrated. The resulting material was purified by silica gel chromatography (0 to 4% MeOH in CH2Cl2) to afford 2-(4-(4-((6-aminopyridazin-3-yl)sulfonyl)piperazin-1-yl)phenyl)-1,1,1,3,3,3-hexafluoro-2-propanol (29 mg) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.40 (s, 1H), 7.67 (d, J=9.4 Hz, 1H), 7.47 (d, J=8.6 Hz, 2H), 7.28 (s, 2H), 7.02 (d, J=9.0 Hz, 2H), 6.89 (d, J=9.2 Hz, 1H), 3.29-3.33 (m, 4H), 3.22-3.28 (m, 4H). m/z (ESI, +ve ion) 485.9 (M+H)+. GK-GKRP IC50 (Binding)=0.285 μM; GK-GKRP EC50 (LC MS/MS-2)=0.302 μM.

후처리

  1. concentrationconcentrated
  2. customThe resulting material was purified by silica gel chromatography (0 to 4% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-ff912096557048a493589630f3deaf5d
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431563B2

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