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Trifluoroacetic acid → N-[2-[[[(4-Fluoro-3-methylphenyl)methyl]amino]carbonyl]-6,7,8,9-tetrahydro-3-hydroxy-7-(methoxymethyl)-4-oxo-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl]-N,N',N'-trimethyl-ethanediamide

HRID 75731
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 75731
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[N:13]=[C:14]3[C:20]4([N:23]([CH3:31])[C:24](=[O:30])[C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH2:21][CH2:22][C:17]([CH2:32][O:33]S(C5C=CC(C)=CC=5)(=O)=O)([CH2:18][CH2:19]4)[CH2:16][N:15]3[C:44](=[O:47])[C:45]=2[OH:46])=[O:11])=[CH:4][C:3]=1[CH3:48].[C:49](C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.F[B-](F)(F)F.C[O+](C)C.CC1C=CC=CN=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[N:13]=[C:14]3[C:20]4([N:23]([CH3:31])[C:24](=[O:30])[C:25]([N:27]([CH3:28])[CH3:29])=[O:26])[CH2:19][CH2:18][C:17]([CH2:32][O:33][CH3:49])([CH2:22][CH2:21]4)[CH2:16][N:15]3[C:44](=[O:47])[C:45]=2[OH:46])=[O:11])=[CH:4][C:3]=1[CH3:48]
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Komponenten

7

Edukt 5

HCID 6422Trifluoroacetic acidHCID 79752-MethylpyridineHCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)2×HCID 86674319N-[2-[[[(4-fluoro-3-methylphenyl)methyl]amino]carbonyl]-6,7,8,9-tetrahydro-3-hydroxy-7-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-4-oxo-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl]-N,N',N'-trimethyl-ethanediamide

Produkt 1

HCID 67960341N-[2-[[[(4-Fluoro-3-methylphenyl)methyl]amino]carbonyl]-6,7,8,9-tetrahydro-3-hydroxy-7-(methoxymethyl)-4-oxo-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl]-N,N',N'-trimethyl-ethanediamideAusbeute 3,79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-[2-[[[(4-fluoro-3-methylphenyl)methyl]amino]carbonyl]-6,7,8,9-tetrahydro-3-hydroxy-7-[[[(4-methylphenyl)sulfonyl]oxy]methyl]-4-oxo-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl]-N,N′,N′-trimethyl-ethanediamide, Intermediate 28, (100 mg, 0.161 mmol) in CH2Cl2 (10 mL) was added 2,6-di-tert-butyl-4-methylpyridine (166 mg, 0.807 mmol) and trimethyloxonium tetrafluoroborate (48.5 mg, 0.807 mmol) and the mixture was stirred at room temp for 16 h. Another 5 equiv each of methylpyridine and trimethyloxonium tetrafluoroborate were added and the mixture was stirred at room temp for 5 h. The reaction was quenched by addition of 1N KHSO4 (30 mL) and stirred for 10 min and extracted with CH2Cl2 (25 mL×2). The combined extracts were dried, filtered and concentrated. The crude material was then dissolved in CH2Cl2 (1 mL) and treated with TFA (1 mL, 12.98 mmol) at room temp for 16 h. The mixture was concentrated in vacuuo and purified by preparative HPLC to afford the title compound (3.5 mg, 6.12 mmol, 3.79% yield) as a thick film. 1H NMR (500 MHz, CDCl3) δ: 12.15 (1H, br. s.), 9.59 (1H, br. s.), 7.24-7.27 (1H, m), 7.17-7.23 (1H, m), 6.90-6.97 (1H, m), 4.71 (1H, d, J=15.6 Hz), 4.58-4.65 (1H, m), 4.43-4.48 (1H, m), 3.51 (1H, d, J=15.6 Hz), 3.39-3.45 (1H, m), 3.20 (2H, d, J=5.8 Hz), 3.05 (3H, s), 3.02 (3H, s), 3.00 (3H, s), 2.27 (3H, d, J=1.8 Hz), 2.08-2.12 (3H, m), 1.76-1.83 (1H, m), 1.66-1.74 (2H, m), 1.38-1.49 (1H, m). LCMS (M+H)=544.5.

Aufarbeitung

  1. stirringthe mixture was stirred at room temp for 5 h
  2. customThe reaction was quenched by addition of 1N KHSO4 (30 mL)
  3. stirringstirred for 10 min
  4. extractionextracted with CH2Cl2 (25 mL×2)
  5. customThe combined extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe crude material was then dissolved in CH2Cl2 (1 mL)
  9. concentrationThe mixture was concentrated in vacuuo
  10. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d29c2e97953849d588aeb51b5cdebb36
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08835411B2

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