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4-Methylmorpholine → 8-anilino-N-hydroxy-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 44609
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 44609
[NH:1]([C:8]1[N:17]=[CH:16][C:15]2[CH2:14][CH2:13][C:12]3[C:18]([C:22]([OH:24])=O)=[N:19][N:20]([CH3:21])[C:11]=3[C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:25][N:26]1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.C1(C(NO)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O>[NH:1]([C:8]1[N:17]=[CH:16][C:15]2[CH2:14][CH2:13][C:12]3[C:18]([C:22]([NH:26][OH:25])=[O:24])=[N:19][N:20]([CH3:21])[C:11]=3[C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11311898TriphenylmethylhydroxylamineHCID 441296031-methyl-8-(phenylamino)-4,5-dihydro-1H-pyrazolo(4,3-h)quinazoline-3-carboxylic acid

Produkt 1

HCID 135980700
8-anilino-N-hydroxy-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide
Ausbeute 66,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 260 mg (0.81 mmol) of 8-anilino-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylic acid in 50 mL of anhydrous dimethylformamide 111 mg of N-hydroxybenzotriazole (0.81 mmol), 0.16 mL of N-methylmorpholine, 205 mg (1.07 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 585 mg (2.13 mmol) of triphenylmethylhydroxylamine were added consecutively. After 48 hours at room temperature the solvent was removed under reduced pressure and the residue taken up with dichloromethane and washed with water. The organic layer was then dried over sodium sulfate and evaporated. The crude was treated with 10 mL of a mixture dichloromethane-trifluoroacetic acid and after 4 hours the volatiles were removed in vacuo. The residue was redissolved with dichloromethane and washed with aqueous NaHCO3 and the product purified by chromatography on a silica gel column, eluted with CH2Cl2—CH3COCH3 4/1, to give 180 mg (66% yield) of the title compound.

Aufarbeitung

  1. customAfter 48 hours at room temperature the solvent was removed under reduced pressure
  2. washwashed with water
  3. dry with materialThe organic layer was then dried over sodium sulfate
  4. customevaporated
  5. additionThe crude was treated with 10 mL of a mixture dichloromethane-trifluoroacetic acid and after 4 hours the volatiles
  6. customwere removed in vacuo
  7. dissolutionThe residue was redissolved with dichloromethane
  8. washwashed with aqueous NaHCO3
  9. customthe product purified by chromatography on a silica gel column
  10. washeluted with CH2Cl2—CH3COCH3 4/1

Quellen und Nachweise

ORD-Eintrag
ord-61a5ed905f3e4f41b55418e755dae444
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08541429B2

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