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Pyridine → 2-methoxy-N-((5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)acetamide

HRID 1049328
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Reaktionsgleichung

Reaktionsgleichung von HRID 1049328
[CH3:1][O:2][CH2:3][C:4]([NH2:6])=[O:5].C(Cl)(=O)[C:8](Cl)=[O:9].[CH3:13][N:14]1[CH:18]=[C:17]([C:19]2[CH:24]=[C:23]([O:25][C:26]3[CH:27]=[CH:28][C:29]([NH2:32])=[N:30][CH:31]=3)[CH:22]=[CH:21][N:20]=2)[CH:16]=[N:15]1.N1C=CC=CC=1>ClCCCl.C1COCC1>[CH3:1][O:2][CH2:3][C:4]([NH:6][C:8](=[O:9])[NH:32][C:29]1[CH:28]=[CH:27][C:26]([O:25][C:23]2[CH:22]=[CH:21][N:20]=[C:19]([C:17]3[CH:16]=[N:15][N:14]([CH3:13])[CH:18]=3)[CH:24]=2)=[CH:31][N:30]=1)=[O:5]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 1400602-MethoxyacetamideHCID 593227775-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)pyridin-2-amine

Produkt 1

HCID 862678492-methoxy-N-((5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)acetamideAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A suspension of Example B6 (0.060 g, 0.673 mmol) in DCE (4 mL) was treated with oxalyl chloride (0.059 mL, 0.673 mmol), stirred at RT for 1 h, then heated to 80° C. for 1.5 h. The mixture was cooled to RT, added drop-wise to a solution of Example A2 (0.15 g, 0.561 mmol) and pyridine (0.226 mL, 2.81 mmol) in THF (4 mL) and stirred at RT overnight. The mixture was treated with satd. Na2CO3, extracted with EtOAc (4×) and the combined organics were dried over Na2SO4 and concentrated to dryness. The material was treated with MeCN, sonicated and the resulting solid collected via filtration to afford 2-methoxy-N-((5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)carbamoyl)acetamide (186 mg, 87%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.78 (s, 1H), 10.71 (s, 1H), 8.37 (d, J=5.7 Hz, 1H), 8.27 (d, J=2.9 Hz, 1H), 8.26 (s, 1H), 8.03 (m, 1H), 7.96 (d, J=0.7 Hz, 1H), 7.74 (dd, J=9.0, 2.9 Hz, 1H), 7.23 (d, J=2.4 Hz, 1H), 6.71 (dd, J=5.7, 2.4 Hz, 1H), 4.11 (s, 2H), 3.84 (s, 3H), 3.34 (s, 3H); MS (ESI) m/z: 383.1 (M+H+).

Aufarbeitung

  1. temperatureheated to 80° C. for 1.5 h
  2. temperatureThe mixture was cooled to RT
  3. stirringstirred at RT overnight
  4. additionThe mixture was treated with satd
  5. extractionNa2CO3, extracted with EtOAc (4×)
  6. dry with materialthe combined organics were dried over Na2SO4
  7. concentrationconcentrated to dryness
  8. additionThe material was treated with MeCN
  9. customsonicated
  10. filtrationthe resulting solid collected via filtration

Quellen und Nachweise

ORD-Eintrag
ord-d74f0eae7c4c40e6a40d747415ff7351
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09382228B2

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