Triethylamine → 4-[5-[4-[amino(methylaminocarbonylimino)methyl]phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide

HRID 376069노트

반응식

HRID 376069 반응식
Cl.N[N:3]=[CH:4][C:5]1[CH:34]=[CH:33][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:30]=[CH:29][C:19]([C:20]([N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])=[O:21])=[CH:18][C:17]=2[O:31][CH3:32])=[CH:7][CH:6]=1.C([N:37](CC)CC)C.[CH3:42][N:43]=[C:44]=[O:45]>C(Cl)Cl>[NH2:3][C:4](=[N:37][C:44]([NH:43][CH3:42])=[O:45])[C:5]1[CH:34]=[CH:33][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:30]=[CH:29][C:19]([C:20]([N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])=[O:21])=[CH:18][C:17]=2[O:31][CH3:32])=[CH:7][CH:6]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 677447554-[5-[4-(aminoiminomethyl)phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide monohydrochloride

생성물 1

HCID 540275584-[5-[4-[amino(methylaminocarbonylimino)methyl]phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A stirred, 0° C. solution of 4-[5-[4-(aminoiminomethyl)phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide monohydrochloride (200 mg, 0.41 mmol) in 4.0 mL anhydrous methylene chloride is treated sequentially with triethylamine (0.068 mL, 0.48 mmol) and methyl isocyanate (0.030 mL, 0.49 mmol). The solution is stirred 30 minutes, concentrated in vacuo and the resulting solids are partitioned between ethyl acetate and water. The organic layer is washed with water and brine, dried over sodium sulfate and concentrated. The resulting material is purified by chromatography on silica gel (15 g) with 70-100% ethyl acetate/hexanes as the eluent to afford 4-[5-[4-[amino(methylaminocarbonylimino)methyl]phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide as a colorless foam:

후처리

  1. concentrationconcentrated in vacuo
  2. customthe resulting solids are partitioned between ethyl acetate and water
  3. washThe organic layer is washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting material is purified by chromatography on silica gel (15 g) with 70-100% ethyl acetate/hexanes as the eluent

출처 및 근거

ORD 기록
ord-959e85ed6cec4c66919e946c2fd78b7e
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05488160

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