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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
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HRID 1987887 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-04ffb41c291b445f94ea5d25b05d44ee
출처 데이터셋
uspto-grants-2009_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07553836B2

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