Hydrochloric Acid → 3-(1-Oxoisoquinolin-2(1H)-yl)-N-cyclopropyl-4-methylbenzamide

HRID 506969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 506969
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C:4](=O)[N:3]1[C:13]1[CH:14]=[C:15]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:16]([NH:18][CH:19]1[CH2:21][CH2:20]1)=[O:17].[BH4-].[Na+].Cl>CO.C(Cl)Cl>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]1[C:13]1[CH:14]=[C:15]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:16]([NH:18][CH:19]1[CH2:21][CH2:20]1)=[O:17]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 670185863-(1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)-N-cyclopropyl-4-methylbenzamide

Produkt 1

HCID 115877673-(1-Oxoisoquinolin-2(1H)-yl)-N-cyclopropyl-4-methylbenzamideAusbeute 51,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-(1,3-dioxo-3,4-dihydroisoquinolin-2(1H)-yl)-N-cyclopropyl-4-methylbenzamide (385 mg) in methanol (8 ml) and methylene chloride (19 ml) under an atmosphere of argon was added NaBH4 (48 mg) portionwise and the reaction stirred at room temperature for 17 hours. Concentrated hydrochloric acid (0.1 ml) was added and the reaction stirred for a further 30 minutes. The reaction mixture was concentrated and the residue resuspended in ethyl acetate, washed 1N NaOH, water, brine, dried (magnesium sulfate) and concentrated to give a white solid which was purified by column chromatography with a gradient of iso-hexane to 80% ethylacetate/iso-hexane to give 3-(1-Oxoisoquinolin-2(1H)-yl)-N-cyclopropyl-4-methylbenzamide as a white solid (190 mg); NMR Spectrum: (DMSOd6) 0.56 (m, 2H), 0.69 (m, 2H), 2.10 (s, 3H), 2.85 (m, 1H), 6.75 (d, 1H), 7.34 (d, 1H), 7.49 (d, 1H), 7.58 (m, 1H), 7.75-7.82 (m, 3H), 7.88 (d, 1H), 8.26 (d, 1H), 8.43 (d, 1H); Mass Spectrum: M+H+ 319.

Aufarbeitung

  1. stirringthe reaction stirred for a further 30 minutes
  2. concentrationThe reaction mixture was concentrated
  3. washwashed 1N NaOH, water, brine
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated
  6. customto give a white solid which
  7. customwas purified by column chromatography with a gradient of iso-hexane to 80% ethylacetate/iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-55f6b6a846704e52be31103e0f130f10
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786115B2

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