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1,2-Dichloroethane → 4-(4-chlorophenyl)-N-(3-methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-1H-pyrrole-2-carboxamide

HRID 1987887
ノート
印刷プレビュー

反応式

HRID 1987887 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:17])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[C:27]([C:30](O)=[O:31])[NH:28][CH:29]=2)=[CH:21][CH:20]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[C:27]([C:30]([NH:17][C:5]3[CH:6]=[CH:7][C:8]([O:9][CH2:10][CH2:11][N:12]4[CH2:16][CH2:15][CH2:14][CH2:13]4)=[C:3]([O:2][CH3:1])[CH:4]=3)=[O:31])[NH:28][CH:29]=2)=[CH:21][CH:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 117365033-Methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)anilineHCID 128970994-(4-Chlorophenyl)-1H-pyrrole-2-carboxylic acid

生成物 1

HCID 672155844-(4-chlorophenyl)-N-(3-methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-1H-pyrrole-2-carboxamide
収率 99%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Following preparation as described in Patent: WO2002/101146, 3-methoxy-4-(2-(pyrrolidin-1-yl)ethoxy)benzenamine (59 mg, 0.25 mol) was stirred overnight in DMF (2 mL) containing with 4-(4-chlorophenyl)-1H-pyrrole-2-carboxylic acid (65 mg, 0.25 mol), EDC (96 mg, 0.50 mol), HOBT (77 mg, 0.50 mol) and NaHCO3 (116 mg, 1.37 mol). After dilution of the reaction with 40 mL of EtOAc, the organic layer was washed with H2O (10 mL×2) and brine. The organic layer was dried over Na2SO4, and conc. in vacuum to a brown oil. The oil was purified by flash column chromatography (silica gel, CH3OH in CH2Cl2, 0-10% gradient) to yield 109 mg (99%) of the title compound as a colorless oil. MS (ESI) 440 (M+H)+.

後処理

  1. custompreparation
  2. washthe organic layer was washed with H2O (10 mL×2) and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customThe oil was purified by flash column chromatography (silica gel, CH3OH in CH2Cl2, 0-10% gradient)

出典と根拠

ORDレコード
ord-04ffb41c291b445f94ea5d25b05d44ee
出典データセット
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07553836B2

反応ノート

読み込み中…

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