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 80778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 80778
[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]

Komponenten

7

Edukt 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

Produkt 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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d97f38b079554c3c89b7e13ce170f177
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846656B2

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