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Potassium Carbonate → 1-(3-(3-bromo-2-methylimidazo[1,2-a]pyridin-8-yloxymethyl)-2,4-dichlorophenyl]-2-[(E)-3-[6-[(E)-2-(pyridin-4-yl)vinyl]pyridin-3-yl]acryloylaminomethyl]pyrrole

HRID 613625
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HRID 613625 반응식
[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([Cl:10])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH2:16][NH:17][C:18](=[O:35])/[CH:19]=[CH:20]/[C:21]1[CH:22]=[N:23][C:24](/[CH:27]=[CH:28]/[C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)=[CH:25][CH:26]=1.CS(Cl)(=O)=O.[Br:41][C:42]1[N:46]2[CH:47]=[CH:48][CH:49]=[C:50](O)[C:45]2=[N:44][C:43]=1[CH3:52].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.C(N(CC)CC)C>[Br:41][C:42]1[N:46]2[CH:47]=[CH:48][CH:49]=[C:50]([O:9][CH2:8][C:7]3[C:2]([Cl:1])=[C:3]([N:11]4[CH:15]=[CH:14][CH:13]=[C:12]4[CH2:16][NH:17][C:18](=[O:35])/[CH:19]=[CH:20]/[C:21]4[CH:22]=[N:23][C:24](/[CH:27]=[CH:28]/[C:29]5[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=5)=[CH:25][CH:26]=4)[CH:4]=[CH:5][C:6]=3[Cl:10])[C:45]2=[N:44][C:43]=1[CH3:52]
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참가 물질

8

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HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 183218891-(2,4-dichloro-3-hydroxymethylphenyl)-2-[(E)-3-[6-[(E)-2-(pyridin-4-yl)vinyl]pyridin-3-yl]acryloylaminomethyl]pyrroleHCID 183219553-Bromo-8-hydroxy-2-methylimidazo[1,2-a]pyridine

생성물 1

HCID 70255217
1-(3-(3-bromo-2-methylimidazo[1,2-a]pyridin-8-yloxymethyl)-2,4-dichlorophenyl]-2-[(E)-3-[6-[(E)-2-(pyridin-4-yl)vinyl]pyridin-3-yl]acryloylaminomethyl]pyrrole
수율 76.9%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

To a solution of 1-(2,4-dichloro-3-hydroxymethylphenyl)-2-[(E)-3-[6-[(E)-2-(pyridin-4-yl)vinyl]pyridin-3-yl]acryloylaminomethyl]pyrrole (70 mg) and triethylamine (28 mg) in N,N-dimethylformamide (1 ml) was added methanesulfonyl chloride (16.7 mg) under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature. To the mixture were added 3-bromo-8-hydroxy-2-methylimidazo[1,2-a]-pyridine (31.4 mg) and potassium carbonate (95.7 mg) at ambient temperature, and the mixture was stirred at the same temperature overnight. Water was added thereto, the resulting precipitates were collected by filtration. The residue was purified by preparative thin layer chromatography (chloroform:methanol=10:1, V/V) to give 1-[3-(3-bromo-2-methylimidazo[1,2-a]pyridin-8-yloxymethyl)-2,4-dichlorophenyl]-2-[(E)-3-[6-[(E)-2-(pyridin-4-yl)vinyl]-pyridin-3-yl]acryloylaminomethyl]pyrrole (76 mg) as yellow amorphous.

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature overnight
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration
  5. customThe residue was purified by preparative thin layer chromatography (chloroform:methanol=10:1, V/V)

출처 및 근거

ORD 기록
ord-17124088613b4d379327f4cda9ca3aec
출처 데이터셋
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06008229

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