2,4-Dichloro-1,3,5-triazine → tert-Butyl 5-(4-chloro-1,3,5-triazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

HRID 1525096

Reaktionsgleichung

Reaktionsgleichung von HRID 1525096
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:23][CH:22]2[CH:18]([CH2:19][NH:20][CH2:21]2)[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].CCN(C(C)C)C(C)C>C(#N)C.[NH4+].[Cl-]>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([N:20]2[CH2:19][CH:18]3[CH2:17][N:16]([C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[CH2:23][CH:22]3[CH2:21]2)[N:7]=1

Komponenten

6

Edukt 3

HCID 178102,4-Dichloro-1,3,5-triazineHCID 81531DiisopropylethylamineHCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylate

Produkt 1

HCID 86669174tert-Butyl 5-(4-chloro-1,3,5-triazin-2-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylateAusbeute 44,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittel2×HCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

To a solution of 2,4-dichloro-1,3,5-triazine (150 mg, 0.953 mmol) in ACN(5 mL) was added a solution of Intermediate 15 (202 mg, 0.953 mmol) and DIPEA (0.33 mL, 1.91 mmol) in ACN (5 mL) at 0° C. dropwise. After 10 min the mixture was diluted with saturated aqueous NH4Cl solution. The aqueous layer was then extracted with DCM and the combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. Chromatography (Hexanes to 80% EtOAc/Hexanes) afforded the desired product as a white solid (137 mg, 44%). MS (ESI) mass calculated for C14H20ClN5O2, 325.13; m/z found, 326.1.

Aufarbeitung

  1. extractionThe aqueous layer was then extracted with DCM
  2. dry with materialthe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bc0519cdef1448afa3d180a71afb5065
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079911B2

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