Acrylic Acid → N-(3-(4-(phenylthio)pyrimidin-2-ylamino)phenyl)acrylamide

HRID 81717

반응식

HRID 81717 반응식
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[CH:16]=3)[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22](O)(=[O:25])[CH:23]=[CH2:24].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.N1(C2C=CN=CC=2)CCCC1>ClCCl>[C:1]1([S:7][C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:16]=[C:17]([NH:21][C:22](=[O:25])[CH:23]=[CH2:24])[CH:18]=[CH:19][CH:20]=3)[N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 5

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 755674-PyrrolidinopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68746426N1-(4-(phenylthio)pyrimidin-2-yl)benzene-1,3-diamine

생성물 1

HCID 59491563N-(3-(4-(phenylthio)pyrimidin-2-ylamino)phenyl)acrylamide수율 33%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of N1-(4-(phenylthio)pyrimidin-2-yl)benzene-1,3-diamine (80 mg, 0.27 mmol) and acrylic acid (37 μL, 0.54 mmol) in anhydrous dichloromethane (2 mL), was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride salt (78 mg, 0.41 mmol), triethylamine (114 μL, 0.82 mmol) and 4-pyrrolidinopyridine (5 mg). The resulting mixture was stirred at room temperature under nitrogen atmosphere for 16 hours. It was diluted with dichloromethane (20 mL), washed with water, 2.0 Maqueous sodium carbonate solution, and dried (Na2SO4). After removal of the solvent in vacuo, the residue was flash chromatographed on silica gel using ethyl acetate:petroleum ether (50:50→100:0) as eluant to give the desired product (31 mg, 33%).

후처리

  1. washwashed with water, 2.0 Maqueous sodium carbonate solution
  2. dry with materialdried (Na2SO4)
  3. customAfter removal of the solvent in vacuo
  4. customchromatographed on silica gel

출처 및 근거

ORD 기록
ord-8ed5f0d69e874edf8a480bbff42c6d10
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846704B2

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