Sodium Hydroxide → 4-(2,2-dimethyl-morpholin-4-ylmethyl)-1-(5-isopropyl-1H-indazol-4-yl)-3-methyl-isoquinolin-6-ol

HRID 606315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 606315
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]1[C:20]([CH:21]([CH3:23])[CH3:22])=[CH:19][CH:18]=[C:17]3[C:13]=1[CH:14]=[N:15][NH:16]3)=[N:7][C:6]([CH3:24])=[C:5]2[CH:25]=O.Cl.[CH3:28][C:29]1([CH3:35])[O:34][CH2:33][CH2:32][NH:31][CH2:30]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>C(Cl)Cl.CC(O)=O>[CH3:28][C:29]1([CH3:35])[O:34][CH2:33][CH2:32][N:31]([CH2:25][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([OH:1])[CH:3]=3)[C:8]([C:12]3[C:20]([CH:21]([CH3:22])[CH3:23])=[CH:19][CH:18]=[C:17]4[C:13]=3[CH:14]=[N:15][NH:16]4)=[N:7][C:6]=2[CH3:24])[CH2:30]1

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 220368882,2-Dimethylmorpholine hydrochlorideHCID 1363416606-hydroxy-1-(5-isopropyl-1H-indazol-4-yl)-3-methyl-isoquinoline-4-carbaldehyde

Produkt 1

HCID 1360104674-(2,2-dimethyl-morpholin-4-ylmethyl)-1-(5-isopropyl-1H-indazol-4-yl)-3-methyl-isoquinolin-6-olAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 6-hydroxy-1-(5-isopropyl-1H-indazol-4-yl)-3-methyl-isoquinoline-4-carbaldehyde (246 mg, 0.71 mmol), 2,2-dimethyl-morpholine hydrochloride (216 mg, 1.4 mmol), NaB(OAc)3H (451 mg, 2.1 mmol), and AcOH (30 uL) in DCM (10 ml) is stirred for 6 h at room temperature. 1N—NaOH (5 ml) is added and the mixture is extracted with DCM. The combined extracts are dried over Na2SO4 and concentrated in vacuo. The residue is chromatographed on silica gel eluting with DCM/MeOH (10:1) to give 207 mg of 4-(2,2-dimethyl-morpholin-4-ylmethyl)-1-(5-isopropyl-1H-indazol-4-yl)-3-methyl-isoquinolin-6-ol.

Aufarbeitung

  1. extractionthe mixture is extracted with DCM
  2. dry with materialThe combined extracts are dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue is chromatographed on silica gel eluting with DCM/MeOH (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-cde5cde8ca114a1a980e4a33279df693
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915288B2

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