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Dimethylformamide → 4-[2-(2,4-Dichloro-phenoxy)-phenylsulfamoyl]-N-{2-oxo-2-[4-(2-pyrrolidin-1-yl-ethyl)-piperazin-1-yl]-ethyl}-benzamide

HRID 446859
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HRID 446859 반응식
[Cl:1][C:2]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][S:12]([C:15]1[CH:27]=[CH:26][C:18]([C:19]([NH:21][CH2:22][C:23](O)=[O:24])=[O:20])=[CH:17][CH:16]=1)(=[O:14])=[O:13].[CH3:33][N:34]([CH3:37])[CH:35]=O.[CH3:38][N:39](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:40].F[P-](F)(F)(F)(F)F.[CH2:62]([N:64]([CH2:67][CH3:68])[CH2:65]C)[CH3:63]>ClCCl>[Cl:1][C:2]1[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([C:19]([NH:21][CH2:22][C:23](=[O:24])[N:39]2[CH2:40][CH2:35][N:34]([CH2:37][CH2:65][N:64]3[CH2:67][CH2:68][CH2:63][CH2:62]3)[CH2:33][CH2:38]2)=[O:20])=[CH:26][CH:27]=1)(=[O:14])=[O:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68493493{4-[2-(2,4-Dichloro-phenoxy)-phenylsulfamoyl]-benzoylamino}-acetic acid

생성물 1

HCID 248127564-[2-(2,4-Dichloro-phenoxy)-phenylsulfamoyl]-N-{2-oxo-2-[4-(2-pyrrolidin-1-yl-ethyl)-piperazin-1-yl]-ethyl}-benzamide
수율 82%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of {4-[2-(2,4-dichloro-phenoxy)-phenylsulfamoyl]-benzoylamino}-acetic acid (42 mg, 0.085 mmol) in a mixture of dichloromethane (2 mL) and dimethylformamide (0.2 mL) 1-(2-pyrrolidin-1-yl-ethyl)-piperazine (EMKA-Chemie) (18 mg, 0.1 mmol), HBTU (46 mg, 0.12 mmol) and triethylamine (60 μL, 0.4 mmol) were added. The mixture was stirred at room temperature for 24 h, then purified by column chromatography using Kieselgel 60 (0.015-0.040 mm) as adsorbent (Merck) and gradient elution starting with 100% A eluent and processing to a mixture of 70% A and 30% B eluent over a period of 15 minutes (eluent A: chloroform; eluent B: methanol containing 5% of ammonium hydroxide) to yield 45.8 mg (82%) of the title compound. MS (EI) 661.2 (MH+).

후처리

  1. additionwere added
  2. custompurified by column chromatography
  3. washas adsorbent (Merck) and gradient elution
  4. additionstarting with 100% A eluent and processing to a mixture of 70% A and 30% B eluent over a period of 15 minutes (eluent A: chloroform; eluent B: methanol containing 5% of ammonium hydroxide)

출처 및 근거

ORD 기록
ord-2e4ea148cb0e4562b3b4e03d1ad23298
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08481527B2

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