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Formaldehyde → Pentafluorophenyl o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate

HRID 1289224
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HRID 1289224 반응식
C=O.[F:3][C:4]1[CH:23]=[C:22]([NH:24][CH:25]2[C:29]3[CH:30]=[C:31]4[C:36](=[CH:37][C:28]=3[CH2:27][CH2:26]2)[N:35]=[C:34]([CH3:38])[N:33]([CH2:39][O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[C:32]4=[O:47])[CH:21]=[CH:20][C:5]=1[C:6]([O:8][C:9]1[C:14]([F:15])=[C:13]([F:16])[C:12]([F:17])=[C:11]([F:18])[C:10]=1[F:19])=[O:7].[C:48]([BH3-])#N.[Na+].O>C(O)(=O)C>[F:3][C:4]1[CH:23]=[C:22]([N:24]([CH3:48])[CH:25]2[C:29]3[CH:30]=[C:31]4[C:36](=[CH:37][C:28]=3[CH2:27][CH2:26]2)[N:35]=[C:34]([CH3:38])[N:33]([CH2:39][O:40][C:41](=[O:46])[C:42]([CH3:43])([CH3:45])[CH3:44])[C:32]4=[O:47])[CH:21]=[CH:20][C:5]=1[C:6]([O:8][C:9]1[C:10]([F:19])=[C:11]([F:18])[C:12]([F:17])=[C:13]([F:16])[C:14]=1[F:15])=[O:7]
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참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 19066345Pentafluorophenyl o-fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate

생성물 1

HCID 19066320Pentafluorophenyl o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

An aqueous solution of formaldehyde (37% weight/volume, 17.55 ml) was added dropwise during 15 minutes to a stirred solution of pentafluorophenyl o-fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate (13 g), prepared as described in Example 1, in glacial acetic acid (100 ml). The mixture was stirred at ambient temperature for 1 hour. Sodium cyanoborohydride (1.36 g) was added portionwise during 30 minutes and the resultant mixture was stirred at ambient temperature for 2 hours. The mixture was poured onto a mixture of ice and water (500 ml) and extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated. The product was purified by column chromatography using increasingly polar mixtures of hexane and ethyl acetate as eluant. There was thus obtained pentafluorophenyl o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate (11 g);

후처리

  1. customprepared
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. customThe product was purified by column chromatography
  6. temperatureusing increasingly polar mixtures of hexane and ethyl acetate as eluant

출처 및 근거

ORD 기록
ord-437402b1b15541b4b1c2f3756e2da3c2
출처 데이터셋
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05747499

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