Acetic Acid → N-((2-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazol-5-yl)methyl)-2-methoxyethanamine

HRID 409952노트

반응식

HRID 409952 반응식
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]([CH3:21])[C:16]([CH:19]=O)=[CH:17][N:18]=3)[S:13][C:6]=12.[CH3:29][O:30][CH2:31][CH2:32][NH2:33].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]([CH3:21])[C:16]([CH2:19][NH:33][CH2:32][CH2:31][O:30][CH3:29])=[CH:17][N:18]=3)[S:13][C:6]=12

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 80182-MethoxyethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 579195642-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazole-5-carbaldehyde

생성물 1

HCID 57919595N-((2-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazol-5-yl)methyl)-2-methoxyethanamine수율 100.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a suspension of 43 (1.3 g, 3.26 mmol) in dry DCM (50 mL) at RT was added 2-methoxyethanamine (1.226 g, 16.32 mmol), acetic acid (0.98 g, 16.32 mmol) and sodium triacetoxyborohydride (3.46 g, 16.32 mmol), and the reaction mixture was stirred at RT for 24 hours. It was then diluted with additional DCM and washed with saturated NaHCO3 solution, dried over Na2SO4, filtered and concentrated to dryness to afford 44 (1.5 g, 100% yield) as an yellow oil which was used crude in the next step with no additional purification. MS (m/z): 458.2 (M+H).

후처리

  1. washwashed with saturated NaHCO3 solution
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-a134b2434a2042208a09c62a648b6e18
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759522B2

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