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

HRID 1258463ノート

反応式

HRID 1258463 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-9cb246d264dd44da904b1281e2360bd7
出典データセット
uspto-grants-2013_06
特許番号
US08466166B2

反応ノート

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