Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 1-oxo-N-[3-(trifluoromethyl)-1,2-oxazol-5-yl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide

HRID 1748347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748347
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:25]=[C:26]1[C:32]2=[CH:33][C:34]3[CH:35]=[CH:36][C:37]([C:40]([OH:42])=O)=[CH:38][C:39]=3[N:31]2[CH2:30][CH2:29][CH2:28][NH:27]1.C(N=P1N(C)CCCN1C)(C)(C)C.[F:56][C:57]([F:65])([F:64])[C:58]1[CH:62]=[C:61]([NH2:63])[O:60][N:59]=1>ClC(Cl)C>[O:25]=[C:26]1[C:32]2=[CH:33][C:34]3[CH:35]=[CH:36][C:37]([C:40]([NH:63][C:61]4[O:60][N:59]=[C:58]([C:57]([F:65])([F:64])[F:56])[CH:62]=4)=[O:42])=[CH:38][C:39]=3[N:31]2[CH2:30][CH2:29][CH2:28][NH:27]1

Komponenten

6

Edukt 4

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 139139963-(Trifluoromethyl)-1,2-oxazol-5-amineHCID 672357061-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid2×HCID 178480484HCID 178480484, Verbindung

Produkt 1

HCID 683233941-oxo-N-[3-(trifluoromethyl)-1,2-oxazol-5-yl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamideAusbeute 15,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of HATU (0.086 g, 0.225 mmol) and 1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid (Intermediate J, 0.050 g, 0.205 mmol) in dichlorethane (1 mL) in a microwave vial is heated in a microwave reactor at 60° C. for 60 minutes. Polystyrene bound 2-tert-butylimino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (0.307 g, 0.615 mmol) and 3-trifluoromethyl-isoxazol-5-ylamine (0.094 g, 0.615 mmol) are added to the mixture and the vial is heated in a microwave at 120° C. for an additional 60 minutes. The resin is filtered off and washed several times with DMF. After the removal of solvent, the residue is purified by flash column chromatography using 5% methanol/dichlorormethane to afford title compound (0.012 g, 15.5%) as a white solid.

Aufarbeitung

  1. additionare added to the mixture
  2. temperaturethe vial is heated in a microwave at 120° C. for an additional 60 minutes
  3. filtrationThe resin is filtered off
  4. washwashed several times with DMF
  5. customAfter the removal of solvent
  6. customthe residue is purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cb794ca266b340dfae756487b04fe00f
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150577B2

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