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Triethylamine → {2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethylamino}-acetic acid methyl ester

HRID 1747431
ノート
印刷プレビュー

反応式

HRID 1747431 の反応式
Br[CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[C:15]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:16]=3[S:17][CH:18]=2)[C:5]1=[O:24].[Cl-].[CH3:26][O:27][C:28]([CH2:30][NH3+:31])=[O:29].CCN(CC)CC.C([O-])([O-])=O.[Na+].[Na+]>CC#N.O>[CH3:26][O:27][C:28](=[O:29])[CH2:30][NH:31][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[C:15]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:16]=3[S:17][CH:18]=2)[C:5]1=[O:24]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471Triethylamine2 回HCID 10340Sodium Carbonate2 回HCID 11105367(Methoxycarbonylmethyl)ammonium chloride2 回HCID 594972451-(2-Bromo-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

生成物 1

HCID 67358337{2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethylamino}-acetic acid methyl ester
収率 98%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

1-(2-Bromo-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (30 mg, 0.075 mmol) is dissolved in CH3CN (0.5 mL)) and Methoxycarbonylmethyl-ammonium chloride (11 mg, 0.09 mmol) and Et3N (0.025 mL, 0.18 mmol) are added. The mixture is first stirred at room temperature for 16 hr. And then 11 mg of Na2CO3 is added and the mixture is stirred at room temperature for another 48 hr. Since the reaction is not completed, another 11 mg of Methoxycarbonylmethyl-ammonium chloride, 0.025 mL of Et3N and 11 mg of Na2CO3 are added. The mixture is then heated at 80° C. for 20 hrs. Then 10 mL of water is added and the mixture is extracted with EtOAc (3×15 mL). The organic layers are combined, dried and concentrated to give crude product. Purification by flash column chromatography affords 30 mg (98%) of {2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethylamino}-acetic acid methyl ester.

後処理

  1. additionare added
  2. stirringthe mixture is stirred at room temperature for another 48 hr
  3. temperatureThe mixture is then heated at 80° C. for 20 hrs
  4. extractionthe mixture is extracted with EtOAc (3×15 mL)
  5. customdried
  6. concentrationconcentrated
  7. customto give crude product
  8. customPurification by flash column chromatography

出典と根拠

ORDレコード
ord-208d8bdf998b4705b45254abc2e752a4
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09150556B2

反応ノート

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