Borohydride → 6-(5-{[(2,2-Dimethylcyclopropylmethyl)amino]methyl]naphthalene-1-yloxy}nicotinamide

HRID 2060901Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2060901
[CH:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][N:15]=1)=O.Cl.[CH3:24][C:25]1([CH3:30])[CH2:27][CH:26]1[CH2:28][NH2:29].C(N(C(C)C)CC)(C)C.[BH4-]>O.CO.C(Cl)Cl>[CH3:24][C:25]1([CH3:30])[CH2:27][CH:26]1[CH2:28][NH:29][CH2:1][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[O:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][N:15]=1

Komponenten

7

Edukt 4

HCID 28123BorohydrideHCID 81531DiisopropylethylamineHCID 53433526(2,2-Dimethylcyclopropyl)methanamine hydrochlorideHCID 594013266-(5-Formylnaphthalen-1-yloxy)nicotinamide

Produkt 1

HCID 594013096-(5-{[(2,2-Dimethylcyclopropylmethyl)amino]methyl]naphthalene-1-yloxy}nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

To a solution of 6-(5-formylnaphthalen-1-yloxy)nicotinamide (Preparation 35) (200 mg, 0.68 mmol) and (2,2-dimethylcyclopropyl)methylamine hydrochloride (111 mg, 0.82 mmol) in a 1:1 mixture of MeOH/DCM (12 mL) was added PS-diisopropylethylamine (3.66 mmol/g, 374 mg, 1.37 mmol) and the reaction was stirred at rt for 16 h. PS-borohydride (2 mmol/g, 1.03 g, 2.05 mmol) was added and the reaction was stirred for 30 min Water (0.5 mL) was added and the mixture purified through an SCX column (10 g/70 mL) eluting with 1% NH4OH in MeOH. Solvent was removed in vacuo and the residue was triturated with EtOAc to give the title compound: RT=2.60 min; m/z (ES+)=376.2 [M+H]+.

Aufarbeitung

  1. additionwas added
  2. customthe mixture purified through an SCX column (10 g/70 mL)
  3. washeluting with 1% NH4OH in MeOH
  4. customSolvent was removed in vacuo
  5. customthe residue was triturated with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-80a63983084c4e23852074da73b27921
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278442B2

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