Hydrochloric Acid → HCID 67387040、化合物

HRID 402035ノート

反応式

HRID 402035 の反応式
[ClH:1].Cl.[CH2:3]([C:7]1[N:8]=[N:9][C:10]([O:30][CH:31]2[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]2)=[CH:11][C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([O:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[C:17]([NH:19][C:20](=[O:22])C)[CH:18]=1)[CH2:4][CH2:5][CH3:6].[C:38]([N:42]=C=O)([CH3:41])([CH3:40])[CH3:39].Cl>C1COCC1.C(Cl)Cl.CCOCC>[ClH:1].[ClH:1].[C:38]([NH:42][C:20]([NH:19][C:17]1[CH:18]=[C:13]([C:12]2[CH:11]=[C:10]([O:30][CH:31]3[CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][CH2:36]3)[N:9]=[N:8][C:7]=2[CH2:3][CH2:4][CH2:5][CH3:6])[CH:14]=[CH:15][C:16]=1[O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:22])([CH3:41])([CH3:40])[CH3:39]

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 62412tert-Butyl isocyanateHCID 67373992HCID 67373992、化合物

生成物 1

HCID 67387040HCID 67387040、化合物収率 126.4%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-[3-butyl-6-(1-methyl-piperidin-4-yloxy)-pyridazin-4-yl]-2-cyclohexyloxy-phenylamine (Example 62, 0.5 mmol, 219 mg) in dry THF (1.0 mL) was added tert-butyl isocyanate (1.5 mmol, 149 mg), and the mixture was stirred at room temperature over night. 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 (5.0 mL), 2N HCl in ether (5.0 mL) was added, kept at room temperature for 10 min, condensed, triturated with hexanes to provide the title compound (193 mg). LCMS: m/z 539 [M+1]. 1H NMR (400 MHz, CD3OD): δ 8.09-8.12 (1H, m), 7.55 and 7.65 (1H, s), 7.12-7.18 (1H, m), 7.00-7.08 (1H, m), 5.36-5.56 (1H, m), 4.41-4.48 (1H, m), 3.25-3.67 (4H, m), 3.08-3.15 (2H, m), 2.93 (3H, s), 2.02-2.58 (6H, m), 1.83-1.89 (2H, m), 1.40-1.70 (8H, m), 1.38 (9H, s), 1.26-1.36 (2H, 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. customcondensed
  5. customtriturated with hexanes

出典と根拠

ORDレコード
ord-78a15e79dd414dac9ada030029126832
出典データセット
uspto-grants-2014_06
特許番号
US08741900B2

反応ノート

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