Triethylamine → N,N,2-Trimethyl-4-[(phenylmethyl)oxy]-1H-benzimidazole-6-carboxamide

HRID 2239290노트

반응식

HRID 2239290 반응식
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[C:8]([C:19]([OH:21])=O)[CH:9]=[C:10]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:4]=2[N:3]=1.Cl.[CH3:23][NH:24][CH3:25].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.CO>[CH3:23][N:24]([CH3:25])[C:19]([C:8]1[CH:9]=[C:10]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:4]2[N:3]=[C:2]([CH3:1])[NH:6][C:5]=2[CH:7]=1)=[O:21]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 685745314-(benzyloxy)-2-methyl-1H-benzo[d]imidazole-6-carboxylic acid

생성물 1

HCID 68574634N,N,2-Trimethyl-4-[(phenylmethyl)oxy]-1H-benzimidazole-6-carboxamide수율 89.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21584119Ethylacetate methanol용매

실험 절차

A mixture of 2-methyl-4-[(phenylmethyl)oxy]-1H-benzimidazole-6-carboxylic acid (5.0 g, 17.7 mmol, STEP 4), dimethylamine hydrochloride (4.33 g, 53.1 mmol), 2-[1H-benzotriazole-1-yl]-1,1,3,3-tetramethyluronium hexafluorophosphate (10.1 g, 26.6 mmol), and triethylamine (10.7 g, 106 mmol) in N,N-dimethylformamide (80 mL) was stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate/methanol (20:1), and washed with saturated ammonium chloride aqueous solution. The organic layer was dried over magnesium sulfate, and concentrated in vacuum. The residue was purified by column chromatography on silica gel (gradient elution from ethyl acetate only to ethyl acetate methanol 5:1) to afford the title compound as a white solid (4.90 g, 89%).

후처리

  1. washwashed with saturated ammonium chloride aqueous solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuum
  4. customThe residue was purified by column chromatography on silica gel (
  5. washgradient elution from ethyl acetate only to ethyl acetate methanol 5:1)

출처 및 근거

ORD 기록
ord-564ba6cec721409a9bbe4db84d6ea342
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723321B2

반응 노트

불러오는 중…