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

HRID 2108833ノート

反応式

HRID 2108833 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-bb625c18640a4b7eb11a684059e04731
出典データセット
uspto-grants-2009_04
特許番号
US07514457B2

反応ノート

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