Potassium Carbonate → 3-Amino-2-chloro-6-methyl-5,6,7,8-tetrahydro[1,6]naphthyridine

HRID 1066769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1066769
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][N:8]([CH3:12])[CH2:9][C:10]=2[CH:11]=1.[Cl:13]N1C(=O)CCC1=O.CC1C=CC(COC(NNC(C2C=NC=CN=2)=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>C(O)(=O)C.O.ClCCl>[NH2:1][C:2]1[C:3]([Cl:13])=[N:4][C:5]2[CH2:6][CH2:7][N:8]([CH3:12])[CH2:9][C:10]=2[CH:11]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 31398ChlorosuccinimideHCID 478568p-tolylmethyl N-(pyrazine-2-carbonylamino)carbamateHCID 117449583-Amino-5,6,7,8-tetrahydro-6-methyl-1,6-naphthyridine

Produkt 1

HCID 211964063-Amino-2-chloro-6-methyl-5,6,7,8-tetrahydro[1,6]naphthyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Amino-6-methyl-5,6,7,8-tetrahydro[1,6]naphthyridine D4 (900 mg, 5.52 mmol) was dissolved in acetic acid (50 ml) before being treated portionwise with N-chlorosuccinimide (1.11 g, 8.28 mmol) 20 min. The reaction mixture was stirred overnight at room temperature under argon. The reaction mixture was diluted with water (125 ml), basified to pH10 with solid K2CO3 and extracted with dichloromethane (×2). The combined organic extracts were washed with sodium bicarbonate, dried (MgSO4) and evaporation in vacuo gave a crude black solid. Flash chromatography using dichloromethane (10% MeOH) gave thetitle compound as a pale orange solid.

Aufarbeitung

  1. extractionextracted with dichloromethane (×2)
  2. washThe combined organic extracts were washed with sodium bicarbonate
  3. customdried
  4. custom(MgSO4) and evaporation in vacuo
  5. customgave a crude black solid
  6. customgave thetitle compound as a pale orange solid

Quellen und Nachweise

ORD-Eintrag
ord-d5c6bf76fcfc4e3797ab47b3513e3f4d
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06245778B1

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