Triethylamine → 7-(Benzyloxy)-1-(2-methoxyethyl)-N,N,2-trimethyl-1H-benzimidazole-5-carboxamide

HRID 1258463노트

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HRID 1258463 반응식
[CH2:1]([O:8][C:9]1[C:14]2[N:15]([CH2:19][CH2:20][O:21][CH3:22])[C:16]([CH3:18])=[N:17][C:13]=2[CH:12]=[C:11]([C:23]([OH:25])=O)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:27][NH:28][CH3:29].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:14]2[N:15]([CH2:19][CH2:20][O:21][CH3:22])[C:16]([CH3:18])=[N:17][C:13]=2[CH:12]=[C:11]([C:23]([N:28]([CH3:29])[CH3:27])=[O:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 672204647-(Benzyloxy)-1-(2-methoxyethyl)-2-methyl-1H-benzimidazole-5-carboxylic acid

생성물 1

HCID 672195137-(Benzyloxy)-1-(2-methoxyethyl)-N,N,2-trimethyl-1H-benzimidazole-5-carboxamide수율 93.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 7-(benzyloxy)-1-(2-methoxyethyl)-2-methyl-1H-benzimidazole-5-carboxylic acid (520 mg, 1.53 mmol, Step 5 of Example 1), dimethylamine hydrochloride (374 mg, 4.58 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (498 mg, 2.60 mmol), 1-hydroxybenzotriazole hydrate (413 mg, 3.06 mmol), and triethylamine (0.64 mL, 4.58 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 1 day. The mixture was poured onto water, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane/methanol (10:1) to afford the title compound as a white solid (524 mg, 93%).

후처리

  1. additionThe mixture was poured onto water
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane/methanol (10:1)

출처 및 근거

ORD 기록
ord-9cb246d264dd44da904b1281e2360bd7
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466166B2

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