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Sodium Hydroxide → (2,6-difluorophenyl)-N-[5-(7-methyl-2H,3H-benzo[e]1,4-dioxin-6-yl)pyrazin-2-yl]carboxamide

HRID 1036142
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1036142
[CH3:1][C:2]1[C:3]([C:12]2[N:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=2)=[CH:4][C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1.[Cl-].[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1.[CH:28](N(C(C)C)CC)(C)C.[OH-:37].[Na+]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=1[C:28]([NH:18][C:15]1[CH:14]=[N:13][C:12]([C:3]2[C:2]([CH3:1])=[CH:11][C:6]3[O:7][CH2:8][CH2:9][O:10][C:5]=3[CH:4]=2)=[CH:17][N:16]=1)=[O:37]
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Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 584871165-(7-methyl-2H,3H-benzo[e]1,4-dioxin-6-yl)pyrazine-2-ylamineHCID 1317308842,6-Difluorobenzol chloride

Produkt 1

HCID 58487017(2,6-difluorophenyl)-N-[5-(7-methyl-2H,3H-benzo[e]1,4-dioxin-6-yl)pyrazin-2-yl]carboxamideAusbeute 9 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 184 (25 mg, 0.1 mmol) in CH2Cl2 was added 4-dimethylaminopyridine (DMAP, 1.2 mg, 0.01 mmol), 2,6-difluorobenzol chloride (53 mg, 0.3 mmol) and diisopropylethylamine (DIEA, 62 mg, 0.48 mmol). The reaction mixture was stirred for 2 h at room temperature. The reaction was quenched with saturated NaHCO3 (20 ml) and extracted with EtOAc. The organic solvent was removed in vacuo. The residue was dissolved in THF:MeOH (1:1) and added 1N NaOH (2 eq). The mixture was stirred for 10 min at ambient temperature. The reaction solution was concentrated in vacuo and residue was extracted with EtOAc. The crude product was purified by ISCO column and HPLC. Fractions containing pure product were combined and evaporated. The white solid 194 (3.3 mg, 9%) was obtained. LC-MS: calcd. for C20H15F2N3O3: 384 (M+1).

Aufarbeitung

  1. customThe reaction was quenched with saturated NaHCO3 (20 ml)
  2. extractionextracted with EtOAc
  3. customThe organic solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in THF:MeOH (1:1)
  5. stirringThe mixture was stirred for 10 min at ambient temperature
  6. concentrationThe reaction solution was concentrated in vacuo and residue
  7. extractionwas extracted with EtOAc
  8. customThe crude product was purified by ISCO column and HPLC
  9. additionFractions containing pure product
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2801b1818f1444f48e3a816ace20b7a8
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08546403B2

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