Hydrochloric Acid → HCID 178468861, 화합물

HRID 230020

반응식

HRID 230020 반응식
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][CH:12]([C:14]2[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=2)[CH3:13])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:25]CN(C(C)C)C(C)C.C(Cl)(Cl)=S.[CH3:38][NH:39][C:40]1[C:41]([NH2:46])=[CH:42][CH:43]=[CH:44][CH:45]=1.Cl>ClCCl.FC(F)(F)C([O-])=O.[Hg+2].FC(F)(F)C([O-])=O>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([C:38]2[N:46]([CH3:25])[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=3[N:39]=2)[CH:12]([C:14]2[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=2)[CH3:13])[CH2:7][CH2:6]1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 10040ThiophosgeneHCID 78498N-Methyl-o-phenylenediamineHCID 81531Diisopropylethylamine2회HCID 178468863HCID 178468863, 화합물

생성물 1

HCID 178468861HCID 178468861, 화합물

시약·촉매·용매 2

HCID 2723924Mercury bis(trifluoroacetate)촉매HCID 6344Dichloromethane용매3회

반응 조건

온도
0 °C

실험 절차

To a 0° C. solution of ethyl 4-{1-[(trans-4-tert-butylcyclohexyl)amino]ethyl}benzoate (0.55 g, 1.66 mmol) and DIEA (0.35 mL, 1.99 mmol) in dry dichloromethane (15 mL) was slowly added thiophosgene (0.13 mL, 1.66 mmol). After stirring at 0° C. for 10 min and then at room temperature for 45 min, a solution of N-methylbenzene-1,2-diamine (0.22 g, 1.83 mmol) and DIEA (0.35 mL, 1.99 mmol) in dry dichloromethane (5 mL) was added. The reaction mixture was stirred for 1 h at ambient temperature and then diluted with dichloromethane (20 mL) and poured into aqueous HCl (1N, 20 mL). The organic layer was separated and washed with aqueous HCl (1N, 20 mL), saturated aqueous NaHCO3 (20 mL), brine (20 mL), dried over Na2SO4 and then concentrated to dryness. The residue was dissolved in dichloromethane (20 mL) and mercury (II) trifluoroacetate (0.80 g, 1.86 mmol) was added. The reaction mixture was stirred for 30 min at room temperature and then filtered through Celite. The organic solution was washed with saturated NaHCO3 (20 mL), dried over Na2SO4 and concentrated. Chromatography (15% EtOAc in Hexane) afforded ethyl 4-{1-[(trans-4-tert-butylcyclohexyl)(1-methyl-1H-benzimidazol-2-yl)amino]ethyl}benzoate. HPLC/MS: m/z=462.4 (M+1), Rt=3.46 min. 1H NMR (500 MHz, CDCl3): □ 8.03 (2H, d, J=8.2 Hz), 7.78 (1H, m), 7.52 (2H, d, J=8.2 Hz), 7.28 (3H, m), 4.80 (1H, q, J=6.5 Hz), 4.39 (2H, q, J=7.5 Hz), 3.72 (3H, s), 2.86 (1H, m), 2.14 (1H, m), 1.94 (1H, m), 1.72-1.64 (2H, m), 1.48 (1H, m), 1.41 (3H, t, J=7.5 Hz), 1.17 (3H, d, J=6.5 Hz), 0.95-0.75 (4H, m), 0.73 (9H, s).

후처리

  1. customTo a 0° C.
  2. waitat room temperature for 45 min
  3. stirringThe reaction mixture was stirred for 1 h at ambient temperature
  4. customThe organic layer was separated
  5. washwashed with aqueous HCl (1N, 20 mL), saturated aqueous NaHCO3 (20 mL), brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness
  8. dissolutionThe residue was dissolved in dichloromethane (20 mL)
  9. stirringThe reaction mixture was stirred for 30 min at room temperature
  10. filtrationfiltered through Celite
  11. washThe organic solution was washed with saturated NaHCO3 (20 mL)
  12. dry with materialdried over Na2SO4
  13. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2b877f7e8745481cafb2e8ba33458b5f
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563815B2

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