Hydrochloric Acid → HCID 67373292、化合物

HRID 1972005ノート

反応式

HRID 1972005 の反応式
[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]

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 67374404HCID 67374404、化合物

生成物 1

HCID 67373292HCID 67373292、化合物収率 117.7%

試薬・触媒・溶媒 4

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 22728543Water ethylacetate溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5b5c62c3ba33418198ef59e6c07a8b36
出典データセット
uspto-grants-2013_04
特許番号
US08431575B2

反応ノート

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