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Water → N-[5-(Pyrido[3,2-e]pyrrolo[1,2-a]pyrazin-5(6H)ylcarbonyl)-2-pyridinyl]-5-fluoro-2-methylbenzamide

HRID 1290946
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HRID 1290946 반응식
[N:1]1[C:10]2[N:9]3[CH:11]=[CH:12][CH:13]=[C:8]3[CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[F:21][C:22]1[CH:23]=[CH:24][C:25]([CH3:40])=[C:26]([CH:39]=1)[C:27]([NH:29][C:30]1[N:35]=[CH:34][C:33]([C:36](Cl)=[O:37])=[CH:32][CH:31]=1)=[O:28].O>ClCCl>[N:1]1[C:10]2[N:9]3[CH:11]=[CH:12][CH:13]=[C:8]3[CH2:7][N:6]([C:36]([C:33]3[CH:32]=[CH:31][C:30]([NH:29][C:27](=[O:28])[C:26]4[CH:39]=[C:22]([F:21])[CH:23]=[CH:24][C:25]=4[CH3:40])=[N:35][CH:34]=3)=[O:37])[C:5]=2[CH:4]=[CH:3][CH:2]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 155082506-(5-Fluoro-2-methylbenzoyl)aminopyridine-3-carbonyl chlorideHCID 189175145,6-Dihydropyrido[3,2-e]pyrrolo[1,2-a]pyrazine

생성물 1

HCID 18917537N-[5-(Pyrido[3,2-e]pyrrolo[1,2-a]pyrazin-5(6H)ylcarbonyl)-2-pyridinyl]-5-fluoro-2-methylbenzamide수율 44.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a chilled (0° C.) solution of 0.343 g of 5,6-dihydropyrido[3,2-e]pyrrolo[1,2-a]pyrazine and 1.1 ml of triethylamine in 5 ml of dichloromethane is added 1.17 g of 6-(5-fluoro-2-methylbenzoyl)aminopyridine-3-carbonyl chloride. The mixture is stirred at room temperature for 16 hours. To the mixture is added 50 ml of dichloromethane and 20 ml of water. The organic layer is separated and washed with 20 ml each of 1M NaHCO3 and brine. The organic layer is dried (Na2SO4) and passed through a thin pad of hydrous magnesium silicate and the pad washed with dichloromethane. The filtrate is concentrated and the residue chromatographed on silica gel prep-plates with ethyl acetate-hexane (1:1) as eluent. The product is crystallized from ethyl acetate to give 0.38 g of white crystals, m.p. 226°-234° C.

후처리

  1. customThe organic layer is separated
  2. washwashed with 20 ml each of 1M NaHCO3 and brine
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. washthe pad washed with dichloromethane
  5. concentrationThe filtrate is concentrated
  6. customthe residue chromatographed on silica gel prep-plates with ethyl acetate-hexane (1:1) as eluent
  7. customThe product is crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-98f295130c4a40b498c9250bc129367e
출처 데이터셋
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05753648

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