Hydrochloric Acid → HCID 67387040, 화합물

HRID 402035노트

반응식

HRID 402035 반응식
[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]

참가 물질

7

반응물 3

HCID 313Hydrochloric AcidHCID 62412tert-Butyl isocyanateHCID 67373992HCID 67373992, 화합물

생성물 1

HCID 67387040HCID 67387040, 화합물수율 126.4%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-78a15e79dd414dac9ada030029126832
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741900B2

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