Triethylamine → Benzyl 2-[3-[(3-[(tert-Butoxycarbonyl)(methyl)amino]methylphenethyl)amino]-5-chloro-6-methyl-2-oxo-1(2H)-pyrazinyl]acetate

HRID 2228731노트

반응식

HRID 2228731 반응식
[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH2:17][NH2:18])[CH:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:20]([O:27][C:28](=[O:40])[CH2:29][N:30]1[C:35](=[O:36])[C:34](Cl)=[N:33][C:32]([Cl:38])=[C:31]1[CH3:39])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:7]([CH2:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[CH2:16][CH2:17][NH:18][C:34]1[C:35](=[O:36])[N:30]([CH2:29][C:28]([O:27][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:40])[C:31]([CH3:39])=[C:32]([Cl:38])[N:33]=1)[CH3:8])=[O:19])([CH3:3])([CH3:2])[CH3:4]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10663926Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetateHCID 18470795tert-Butyl N-[3-(2-aminoethyl)benzyl]-N-methylcarbamate

생성물 1

HCID 18470853Benzyl 2-[3-[(3-[(tert-Butoxycarbonyl)(methyl)amino]methylphenethyl)amino]-5-chloro-6-methyl-2-oxo-1(2H)-pyrazinyl]acetate수율 75%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

tert-Butyl-N-[3-(2-aminoethyl)benzyl]-N-methylcarbamate (preparation 15) (0.5 g, 1.89 mmol), benzyl-2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate (preparation 17) (0.6 g, 1.83 mmol) and triethylamine (0.5 ml, 3.66 mmol) in ethyl acetate (30 ml) were stirred at reflux for 24 hr. The resultant mixture was diluted with ethyl acetate (20 ml) and washed with water, sat aq brine, dried over MgSO4. Removal of the drying agent by filtration followed by evaporation of the solvent gave a red oil which was purified by chromatography (SiO2, gradient elution with 100% CH2Cl2; 99:1 CH2Cl2:MeOH; 98:2 CH2Cl2:MeOH) to give the desired product (0.76 g, 75%). 1H NMR (CDCl3) δ 1.45 (s, 9H), 2.20 (s, 3H), 2.80 (s, br, 3H), 2.90 (t, 2H), 3.70 (m, 2H), 4.20 (s, br, 2H), 4.80 (s, 2H), 5.20 (s, 2H), 6.10 (m, br, 1H), 7.10 (m, 3H), 7.25 (m, 1H), 7.35 (m, 5H). LRMS m/z=555.3 (M+1)+. Found C, 62.50, H, 6.34, N, 9.98%; C29H35N4O5Cl requires C, 62.75, H, 6.36, N, 10.09%.

후처리

  1. temperatureat reflux for 24 hr
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. customRemoval of the drying agent
  5. filtrationby filtration
  6. customfollowed by evaporation of the solvent
  7. customgave a red oil which
  8. customwas purified by chromatography (SiO2, gradient elution with 100% CH2Cl2; 99:1 CH2Cl2:MeOH; 98:2 CH2Cl2:MeOH)

출처 및 근거

ORD 기록
ord-7f0f8f459d1c4ae6b6409f6927cad00d
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06417203B1

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