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Cesium carbonate → 2-[(5-Chloro-2-{[4-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide

HRID 1472551
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1472551
Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([NH:13][O:14][CH3:15])=[O:12])[C:5]([Cl:20])=[CH:4][N:3]=1.[CH3:21][C:22]1[CH:23]=[N:24][N:25]([CH:28]([CH3:30])[CH3:29])[C:26]=1[NH2:27].C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[Cl:20][C:5]1[C:6]([NH:8][C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([NH:13][O:14][CH3:15])=[O:12])=[CH:7][C:2]([NH:27][C:26]2[N:25]([CH:28]([CH3:30])[CH3:29])[N:24]=[CH:23][C:22]=2[CH3:21])=[N:3][CH:4]=1
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Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 290606024-methyl-1-(propan-2-yl)-1H-pyrazol-5-amineHCID 575168962-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide

Produkt 1

HCID 462150982-[(5-Chloro-2-{[4-methyl-1-(1-methylethyl)-1H-pyrazol-5-yl]amino}-4-pyridinyl)amino]-N-(methyloxy)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A microwave tube was charged with 2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide (100 mg, 0.32 mmol), 4-methyl-1-(1-methylethyl)-1H-pyrazol-5-amine (93.6 mg, 0.67 mmol), cesium carbonate (312.8 mg, 0.96 mmol) and DMF (5 mL). The reaction mixture was degassed under nitrogen for 10 min and palladium (II) acetate (3.6 mg, 0.016 mmol) and BINAP (19.9 mg, 0.032 mmol) were added. The reaction mixture was heated in an oil bath for 6 hours and then in a microwave at 150° C. for 40 min. The solvent was evaporated and the residue dissolved in MeOH. It was filtered thru celite and thru an Acrodisc to be purified on preparative Agilent HPLC (5 to 95% water:acetonitrile with 0.1% formic acid). Fractions were combined and evaporated. The brown oil residue was diluted in DMF and water was added. A precipitate crashed out. It was filtered and dried under vacuum at 40° C. for 6 hrs. LC-MS [M+H]+=415.1. 1H NMR (400 MHz, DMSO-d6) ppm 11.93 (s, 1 H) 9.48 (br. s., 1 H) 8.23 (s, 1 H) 7.93 (s, 1 H) 7.58 (d, J=7.83 Hz, 1 H) 7.50 (d, J=3.79 Hz, 2 H) 7.24 (s, 1 H) 7.12 (dt, J=7.83, 4.17 Hz, 1 H) 6.40 (br. s., 1 H) 4.33 (dt, J=13.14, 6.57 Hz, 1 H) 3.71 (s, 3 H) 1.78 (s, 3 H) 1.26 (d, J=6.57 Hz, 6 H).

Aufarbeitung

  1. customThe reaction mixture was degassed under nitrogen for 10 min
  2. temperatureThe reaction mixture was heated in an oil bath for 6 hours
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in MeOH
  5. filtrationIt was filtered thru celite
  6. customto be purified on preparative Agilent HPLC (5 to 95% water:acetonitrile with 0.1% formic acid)
  7. customevaporated
  8. additionThe brown oil residue was diluted in DMF
  9. additionwater was added
  10. filtrationIt was filtered
  11. customdried under vacuum at 40° C. for 6 hrs

Quellen und Nachweise

ORD-Eintrag
ord-9644236bb312404c974d6e16f62ff0ca
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09012479B2

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