Tetrahydrofuran → 2-(4-tert-Butyl-3-chlorophenoxy)-N-[(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)methyl]acetamide

HRID 2108833노트

반응식

HRID 2108833 반응식
C1COCC1.[C:6]([C:10]1[CH:20]=[CH:19][C:13]([O:14][CH2:15][C:16]([OH:18])=O)=[CH:12][C:11]=1[Cl:21])([CH3:9])([CH3:8])[CH3:7].C1N=CN(C(N2C=NC=C2)=O)C=1.C(C1C=CC(OCC([NH:46][CH2:47][C:48]2[CH:57]=[CH:56][C:51]3[NH:52][C:53](=[O:55])[NH:54][C:50]=3[CH:49]=2)=O)=CC=1)(C)(C)C>C(N(CC)CC)C>[C:6]([C:10]1[CH:20]=[CH:19][C:13]([O:14][CH2:15][C:16]([NH:46][CH2:47][C:48]2[CH:57]=[CH:56][C:51]3[NH:52][C:53](=[O:55])[NH:54][C:50]=3[CH:49]=2)=[O:18])=[CH:12][C:11]=1[Cl:21])([CH3:7])([CH3:8])[CH3:9]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 159797742-(4-Tert-butylphenoxy)-n-[(2-oxo-2,3-dihydro-1h-benzimidazol-5-yl)methyl]acetamideHCID 21097497(4-tert-Butyl-3-chlorophenoxy)acetic acid

생성물 1

HCID 159797772-(4-tert-Butyl-3-chlorophenoxy)-N-[(2-oxo-2,3-dihydro-1H-benzimidazol-5-yl)methyl]acetamide수율 11%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

To a THF (3.0 ml) solution of the compound of 4A (109 mg, 0.45 mmol) was added CDI (73 mg, 0.45 mmol) at room temperature and the mixture was stirred for 2 hours followed by the additional stirring for 10 hours after the injection of triethylamine (0.3 ml) and the amine compound of Example 1 (156 mg, 0.5 mmol). The resulting precipitate was removed by filtration, followed by evaporation under reduced pressure to give the crude residue which was purified through silica gel column chromatography eluting with DCM/MeOH (9:1) to furnish the title compound as a white solid (19 mg, 11%). 1H NMR (CDCl3): δ 1.40 (9H, s), 4.29 (2H, d, J=5.9 Hz), 4.53 (2H, s), 6.78-6.92 (4H, m), 7.01 (1H, d, J=2.6 Hz), 7.37 (1H, d, J=8.5 Hz), 8.61 (1H, bt, J=6.6 Hz), 10.55, 1H, bs), 10.57 (1H, bs). MS (ESI) m/z 388 (M+H)+.

후처리

  1. customThe resulting precipitate was removed by filtration
  2. customfollowed by evaporation under reduced pressure
  3. customto give the crude residue which
  4. customwas purified through silica gel column chromatography
  5. washeluting with DCM/MeOH (9:1)

출처 및 근거

ORD 기록
ord-bb625c18640a4b7eb11a684059e04731
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514457B2

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