Water → HCID 25117579, compound

HRID 2060896Notes

Reaction equation

HRID 2060896 reaction equation
[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][N:15]=2)=[CH:5][CH:4]=1)=O.[CH:23]1([CH2:28][CH2:29][NH2:30])[CH2:27][CH2:26][CH2:25][CH2:24]1.[BH4-].[Na+].O>CO>[CH:23]1([CH2:28][CH2:29][NH:30][CH2:1][C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]([O:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[CH:16][N:15]=3)=[CH:5][CH:4]=2)[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 53056502-CyclopentylethanamineHCID 59401307HCID 59401307, compound

Product 1

HCID 25117579HCID 25117579, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-(4-formylnaphthalen-1-yloxy)nicotinamide (Preparation 2) (200 mg, 0.7 mmol) in MeOH (10 mL) was added 2-cyclopentyl ethylamine (116 mg, 1.0 mmol) and 4 Å molecular sieves (200 mg). The mixture was stirred for 16 h before adding NaBH4 (130 mg, 3.4 mmol). After 1.5 h water (1 mL) was added and the mixture filtered. Solvent was removed in vacuo and the residue purified by column chromatography (0.5% NH3: 2% MeOH:DCM) to give the title compound: RT=2.68 min; m/z (ES+)=390.2 [M+H]+.

Workup

  1. filtrationthe mixture filtered
  2. customSolvent was removed in vacuo
  3. customthe residue purified by column chromatography (0.5% NH3: 2% MeOH:DCM)

Sources & evidence

ORD record
ord-323c30ad311d42b8b3a688fc8d31869d
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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