Trifluoroacetic acid → (R)-1-(4-(6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)ethanone

HRID 80778노트

반응식

HRID 80778 반응식
[C:1](O)([C:3](F)(F)F)=[O:2].[CH:8]([C:11]1[CH:12]=[CH:13][C:14]([CH3:54])=[C:15]([N:17]2[CH2:53][CH2:52][C:20]3[N:21]=[C:22]([C:32]4[CH:40]=[CH:39][CH:38]=[C:37]5[C:33]=4[C:34]([CH3:51])=[CH:35][N:36]5[S:41]([C:44]4[CH:50]=[CH:49][C:47]([CH3:48])=[CH:46][CH:45]=4)(=[O:43])=[O:42])[N:23]=[C:24]([N:25]4[CH2:30][CH2:29][NH:28][CH2:27][C@H:26]4[CH3:31])[C:19]=3[CH2:18]2)[CH:16]=1)([CH3:10])[CH3:9].C(OC(=O)C)(=O)C.CCN(C(C)C)C(C)C>C(Cl)Cl.CCOC(C)=O>[CH:8]([C:11]1[CH:12]=[CH:13][C:14]([CH3:54])=[C:15]([N:17]2[CH2:53][CH2:52][C:20]3[N:21]=[C:22]([C:32]4[CH:40]=[CH:39][CH:38]=[C:37]5[C:33]=4[C:34]([CH3:51])=[CH:35][N:36]5[S:41]([C:44]4[CH:45]=[CH:46][C:47]([CH3:48])=[CH:49][CH:50]=4)(=[O:42])=[O:43])[N:23]=[C:24]([N:25]4[CH2:30][CH2:29][N:28]([C:1](=[O:2])[CH3:3])[CH2:27][C@H:26]4[CH3:31])[C:19]=3[CH2:18]2)[CH:16]=1)([CH3:10])[CH3:9]

참가 물질

7

반응물 4

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 71240674(R)-6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(2-methylpiperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

생성물 1

HCID 71240550(R)-1-(4-(6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)ethanone

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

The TFA salt of (R)-6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(2-methylpiperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (62 mg, 0.095 mmol) was dissolved in DCM (5 mL) and acetic anhydride (0.014 mL, 0.143 mmol) and DIEA (0.133 mL, 0.764 mmol) were added. The reaction was stirred at rt for 45 min and diluted with EtOAc, and washed successively with sat NaHCO3 and brine. The organic layer was then dried over Na2SO4 and filtered. After concentration, the resulting residue was purified by FCC (60-90% EtOAc/heptane) to provide (R)-1-(4-(6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)ethanone. MS (ESI+) m/z 691.4 (M+H)+.

후처리

  1. washwashed successively with sat NaHCO3 and brine
  2. dry with materialThe organic layer was then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationAfter concentration
  5. customthe resulting residue was purified by FCC (60-90% EtOAc/heptane)

출처 및 근거

ORD 기록
ord-d97f38b079554c3c89b7e13ce170f177
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846656B2

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