Hydrochloric Acid → HCID 67373292, 화합물

HRID 1972005노트

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HRID 1972005 반응식
[ClH:1].Cl.[CH2:3]([C:7]1[N:8]=[N:9][C:10]([O:31][CH:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)=[CH:11][C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[C:17]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:18]=1)[CH2:4][CH2:5][CH3:6].[CH2:39](Br)[CH:40]([CH3:42])[CH3:41].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.O.CCOC(C)=O.C(Cl)Cl.CCOCC>[ClH:1].[ClH:1].[CH2:3]([C:7]1[N:8]=[N:9][C:10]([O:31][CH:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)=[CH:11][C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([O:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[C:17]([N:19]([CH2:39][CH:40]([CH3:42])[CH3:41])[S:20]([CH3:23])(=[O:21])=[O:22])[CH:18]=1)[CH2:4][CH2:5][CH3:6]

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 67374404HCID 67374404, 화합물

생성물 1

HCID 67373292HCID 67373292, 화합물수율 117.7%

시약·촉매·용매 4

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 22728543Water ethylacetate용매

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온도
90 °C

실험 절차

To a solution of N-{5-[3-butyl-6-(1-methyl-piperidin-4-yloxy)-pyridazin-4-yl]-2-cyclohexyloxy-phenyl}-methanesulfonamide dihydrochloride (0.1 mmol, 59 mg) in DMF (1.0 mL) was added isobutyl bromide (0.2 mmol, 22 μL), and potassium carbonate (0.4 mmol, 56 mg). And the mixture was stirred at 90° C. for 2 hours. It was then diluted with water/EtOAc. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (DCM to DCM+10% 2N NH3 in MeOH) to give a colorless sticky solid, which was dissolved in DCM (1.0 mL), 2N HCl in ether (1.0 mL) was added, condensed, triturated with hexanes to provide the title compound (38 mg). LCMS: m/z 574 [M+1]. 1H NMR (400 MHz, CD3OD): δ 7.39 (1H, d), 7.31 (1H, s), 7.25 (1H, d), 7.04 (1H, s), 5.42 (1H, bs), 4.46-4.53 (1H, m), 3.42-3.48 (1H, m), 2.98-3.30 (5H, m), 2.95 (3H, s), 2.90-2.94 (2H, m), 2.69 (3H, s), 2.09-2.30 (6H, m), 1.82-1.88 (2H, m), 1.20-1.69 (11H, m), 0.89-0.93 (6H, m), 0.79 (3H, t).

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by silica gel chromatography (DCM to DCM+10% 2N NH3 in MeOH)
  3. customto give a colorless sticky solid, which
  4. customcondensed
  5. customtriturated with hexanes

출처 및 근거

ORD 기록
ord-5b5c62c3ba33418198ef59e6c07a8b36
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431575B2

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