Methanesulfonyl chloride → Methyl 8-[bis-(tert-butoxycarbonyl)amino]-pyrazolo[5,1-a]isoquinoline-7-carboxylate

HRID 595105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595105
CS(Cl)(=O)=O.[C:6]([O:10][C:11]([N:13]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:14]1[CH:23]=[CH:22][C:21]2[C:20]3=[CH:24][CH:25]=[N:26][N:19]3[CH2:18][CH:17](O)[C:16]=2[C:15]=1[C:28]([O:30][CH3:31])=[O:29])=[O:12])([CH3:9])([CH3:8])[CH3:7]>C(N(CC)CC)C.C(Cl)Cl>[C:35]([O:34][C:32]([N:13]([C:11]([O:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:12])[C:14]1[CH:23]=[CH:22][C:21]2[C:20]3=[CH:24][CH:25]=[N:26][N:19]3[CH:18]=[CH:17][C:16]=2[C:15]=1[C:28]([O:30][CH3:31])=[O:29])=[O:33])([CH3:38])([CH3:37])[CH3:36]

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 71005652Methyl 8-[bis-(tert-butoxycarbonyl)amino]-6-hydroxy-5,6-dihydro-pyrazolo[5,1-a]isoquinoline-7-carboxylate2×

Produkt 1

HCID 70984535Methyl 8-[bis-(tert-butoxycarbonyl)amino]-pyrazolo[5,1-a]isoquinoline-7-carboxylateAusbeute 100,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Methanesulfonyl chloride (0.5 mL) was added to a solution of methyl 8-[bis-(tert-butoxycarbonyl)amino]-6-hydroxy-5,6-dihydro-pyrazolo[5,1-a]isoquinoline-7-carboxylate (Intermediate 8, 0.290 g) in triethylamine (0.7 mL) and DCM (10 mL) and the reaction mixture was stirred at room temperature for 30 minutes. The resultant mixture was washed with 1M aqueous hydrochloric acid and the organic layer was separated, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to give methyl 8-[bis-(tert-butoxycarbonyl)amino]-pyrazolo[5,1-a]isoquinoline-7-carboxylate (0.280 g) as a gum.

Aufarbeitung

  1. washThe resultant mixture was washed with 1M aqueous hydrochloric acid
  2. customthe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c7209ccaa39648919564c25d4ec7b1fc
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242997B2

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