Triethylamine → Methyl 4-chloro-1-(3-hydroxypropyl)-2-[(2,4,6-trichlorophenyl)amino]-1H-benzimidazole-7-carboxylate

HRID 1628554노트

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HRID 1628554 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:12][CH2:13][CH2:14][CH2:15][OH:16])[C:3]=1[NH:17][C:18](=S)[NH:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([Cl:27])=[CH:22][C:21]=1[Cl:28].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[C:3]2[N:17]=[C:18]([NH:19][C:20]3[C:25]([Cl:26])=[CH:24][C:23]([Cl:27])=[CH:22][C:21]=3[Cl:28])[N:12]([CH2:13][CH2:14][CH2:15][OH:16])[C:4]=2[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86632911Methyl 4-chloro-2-[(3-hydroxypropyl)amino]-3-{[(2,4,6-trichlorophenyl)carbamothioyl]amino}benzoate

생성물 1

HCID 68761466Methyl 4-chloro-1-(3-hydroxypropyl)-2-[(2,4,6-trichlorophenyl)amino]-1H-benzimidazole-7-carboxylate수율 96.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

A mixture of methyl 4-chloro-2-[(3-hydroxypropyl)amino]-3-{[(2,4,6-trichlorophenyl)carbamothioyl]amino}benzoate (285 mg, 0.574 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (121 mg, 0.631 mmol) and triethylamine (0.0880 mL, 0.631 mmol) in tetrahydrofuran (6 mL) was stirred at 50° C. for 14 hr. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (256 mg, 0.553 mmol, 96%).

후처리

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture

출처 및 근거

ORD 기록
ord-04b8d64b39324386a6fbc609e2a7c807
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785460B2

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