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Morpholine → N-[5-(3-Methoxy-phenyl)-1H-pyrazol-3-yl]-4-morpholin-4-yl-butyramide

HRID 1695217
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1695217
COC1C=C(C2C=C(N)NN=2)C=CC=1.C(N(C(C)C)CC)(C)C.Br[CH2:25][CH2:26][CH2:27][C:28]([NH:30][C:31]1[CH:35]=[C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[CH:37]=2)[NH:33][N:32]=1)=[O:29].[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>CC(N(C)C)=O.C(Cl)Cl>[CH3:43][O:42][C:38]1[CH:37]=[C:36]([C:34]2[NH:33][N:32]=[C:31]([NH:30][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)[CH:35]=2)[CH:41]=[CH:40][CH:39]=1
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Komponenten

7

Edukt 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 671875504-bromo-N-[5-(3-methoxy-phenyl)-1H-pyrazol-3-yl]-butyramideHCID 178489814HCID 178489814, Verbindung

Produkt 1

HCID 25029480N-[5-(3-Methoxy-phenyl)-1H-pyrazol-3-yl]-4-morpholin-4-yl-butyramide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 31374DimethylacetamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 4-bromobutyryl chloride chloride (0.104 mL, 0.9 mmol) in dry DMA (1 mL) was cooled to −10° C. (ice/water bath) under N2; 5-(3-methoxy-phenyl)-2H-pyrazol-3-ylamine (170 mg, 0.9 mmol) and diisopropylethylamine (0.315 mL, 1.8 mmol) in dry DMA (1 ml) were added. Upon complete conversion to the intermediate 4-bromo-N-[5-(3-methoxy-phenyl)-1H-pyrazol-3-yl]-butyramide (as monitored by LC-MS), morpholine (0.079 mL, 0.9 mmol) was added and the mixture was heated at 60° C. for 16 hours. The residue was dissolved in DCM (2 mL) and washed with sat. Na2CO3 solution, The organic phase was concentrated under reduced pressure and the crude product was purified by SiO2 column (gradient from Acetonitrile 100% to MeCN/MeOH, NH3 90/10). The fractions containing the title compound were collected to afford 17 mg (5.5% of yield).

Aufarbeitung

  1. washwashed with sat. Na2CO3 solution
  2. concentrationThe organic phase was concentrated under reduced pressure
  3. customthe crude product was purified by SiO2 column (gradient from Acetonitrile 100% to MeCN/MeOH, NH3 90/10)
  4. additionThe fractions containing the title compound
  5. customwere collected
  6. customto afford
  7. custom17 mg (5.5% of yield)

Quellen und Nachweise

ORD-Eintrag
ord-51f93f3ebe0040c5bece6048fd271d5b
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08163729B2

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