Chloroacetyl chloride → 2-chloro-N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N-methylacetamide

HRID 1668401노트

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HRID 1668401 반응식
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:18][C:17]3[C:16](=[O:19])[N:15]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([CH2:28][NH:29][CH3:30])=[CH:24][CH:23]=4)[CH:14]=[N:13][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1.[Cl:31][CH2:32][C:33](Cl)=[O:34].C(N(CC)CC)C.O1CCCC1>C(OCC)(=O)C>[Cl:31][CH2:32][C:33]([N:29]([CH2:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][CH2:20][N:15]2[C:16](=[O:19])[C:17]3[S:18][C:10]([C:7]4[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=4)=[CH:11][C:12]=3[N:13]=[CH:14]2)=[CH:23][CH:24]=1)[CH3:30])=[O:34]

참가 물질

6

반응물 4

HCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 673596986-(4-chlorophenyl)-3-(2-{4-[(methylamino)methyl]phenyl}ethyl)thieno[3,2-d]pyrimidin-4(3H)-one dihydrochloride

생성물 1

HCID 592398302-chloro-N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N-methylacetamide수율 64.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

A mixture of the compound (200 mg) obtained in Example 4, chloroacetyl chloride (51 mg), triethylamine (146 mg) and tetrahydrofuran (2 ml) was stirred at 60° C. for 1 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography [developing solvent:ethyl acetate-methanol (20:1, volume ratio)] and crystallized from hexane to give the title compound (130 mg) as a colorless powder.

후처리

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography [developing solvent:ethyl acetate-methanol (20:1, volume ratio)]
  5. customcrystallized from hexane

출처 및 근거

ORD 기록
ord-5ad54534f75d4252ba8ceea86b15a4f9
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989445B2

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