Hydrochloric Acid → HCID 67373992、化合物

HRID 1972002ノート

反応式

HRID 1972002 の反応式
[ClH:1].Cl.Cl.[CH2:4]([C:8]1[N:9]=[N:10][C:11]([O:28][CH:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[CH:12][C:13]=1[C:14]1[CH:15]=[CH:16][C:17]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:18]([NH2:20])[CH:19]=1)[CH2:5][CH2:6][CH3:7].[C:36]([Cl:39])(=[O:38])[CH3:37].CCN(C(C)C)C(C)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOCC>[ClH:39].[ClH:1].[CH2:4]([C:8]1[N:9]=[N:10][C:11]([O:28][CH:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[CH:12][C:13]=1[C:14]1[CH:15]=[CH:16][C:17]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:18]([NH:20][C:36](=[O:38])[CH3:37])[CH:19]=1)[CH2:5][CH2:6][CH3:7]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 67374073HCID 67374073、化合物

生成物 1

HCID 67373992HCID 67373992、化合物収率 55.1%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 5-[3-butyl-6-(1-methyl-piperidin-4-yloxy)-pyridazin-4-yl]-2-cyclohexyloxy-phenylamine trihydrochloride (0.2 mmol, 110 mg) in DCM (1.0 mL) at 0° C. was added acetyl chloride (0.4 mmol, 29 μL), DIEA (0.4 mmol, 70 μL) and DMAP (5 mg). And the mixture was stirred at room temperature for 1 hour. It was then condensed 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, kept at room temperature for 10 min, condensed, triturated with hexanes to provide the title compound (61 mg). LCMS: m/z 482 [M+1]. 1H NMR (400 MHz, CDCl3): δ 8.43 (1H, s), 7.89 (1H, s), 6.97 (2H, s), 6.81 (1H, s), 5.60 (1H, bs), 4.37-4.43 (1H, m), 3.10-3.45 (4H, m), 2.90-2.95 (2H, m), 2.81 (3H, s), 2.35-2.61 (4H, m), 2.23 (3H, s), 1.25-1.87 (14H, m), 0.83 (3H, t).

後処理

  1. customcondensed 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. waitkept at room temperature for 10 min
  5. customcondensed
  6. customtriturated with hexanes

出典と根拠

ORDレコード
ord-e11fb8e592434f09912daaad192fd698
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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