Triethylamine → 2-nitro-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide

HRID 2374864노트

반응식

HRID 2374864 반응식
[NH2:1][CH:2]([C:4]1[N:9]=[N:8][C:7]([NH:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=2)=[N:6][CH:5]=1)[CH3:3].C(N(CC)CC)C.[N+:30]([C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35](Cl)=[O:36])([O-:32])=[O:31]>ClCCl>[N+:30]([C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35]([NH:1][CH:2]([C:4]1[N:9]=[N:8][C:7]([NH:10][C:11]2[CH:12]=[C:13]([O:21][CH3:22])[C:14]([O:19][CH3:20])=[C:15]([O:17][CH3:18])[CH:16]=2)=[N:6][CH:5]=1)[CH3:3])=[O:36])([O-:32])=[O:31]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 118752-Nitrobenzoyl chlorideHCID 534044296-(1-aminoethyl)-N-(3,4,5-trimethoxyphenyl)-1,2,4-triazin-3-amine2회

생성물 1

HCID 587119782-nitro-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide수율 26.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 6-(1-aminoethyl)-N-(3,4,5-trimethoxyphenyl)-1,2,4-triazin-3-amine (Intermediate 9) (0.30 g, 1.0 mmol) in dichloromethane (10 mL) cooled to −78° C. was added triethylamine (0.42 mL, 3.0 mmol) and 2-nitrobenzoyl chloride (0.35 mL, 1.5 mmol). After stirring for one hour, the solution was quenched with water and allowed to warm to room temperature. The solution was diluted with dichloromethane (50 mL) and washed with 0.1N HCl (2×50 mL) and brine (50 mL). The solution was dried with magnesium sulfate and filtered, and silica gel (5 g) was added to the solution, followed by evaporation of the volatiles under reduced pressure. The pre-adsorbed solids were loaded into a solid loading cartridge and subjected to a gradient elution using ethyl acetate:hexane (20:80) to ethyl acetate:hexanes (100:0) using a RediSep silica gel cartridge (12 g; ISCO). The appropriate fractions were combined and concentrated under reduced pressure to give 2-nitro-N-(1-{3-[(3,4,5-trimethoxyphenyl)amino]-1,2,4-triazin-6-yl}ethyl)benzamide (0.12 g) as a white solid. MS m/z455 (M+1).

후처리

  1. customthe solution was quenched with water
  2. additionThe solution was diluted with dichloromethane (50 mL)
  3. washwashed with 0.1N HCl (2×50 mL) and brine (50 mL)
  4. dry with materialThe solution was dried with magnesium sulfate
  5. filtrationfiltered
  6. additionsilica gel (5 g) was added to the solution
  7. customfollowed by evaporation of the volatiles under reduced pressure
  8. washsubjected to a gradient elution
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-06ff9961733e4e0c84f8c5e2b1f880d0
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07462614B2

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