Water → 4-{4-[(3-Methylbutylamino) methyl]isoquinolin-1-yloxy}benzamide

HRID 2060897Notes

Reaction equation

HRID 2060897 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][CH:15]=2)=[N:5][CH:4]=1)=O.[CH3:23][CH:24]([CH3:28])[CH2:25][CH2:26][NH2:27].[BH4-].[Na+].O>CN(C=O)C>[CH3:23][CH:24]([CH3:28])[CH2:25][CH2:26][NH:27][CH2:1][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][CH:15]=2)=[N:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7894IsoamylamineHCID 4311764Sodium borohydrideHCID 594012974-(4-Formylisoquinolin-1-yloxy)benzamide

Product 1

HCID 251211304-{4-[(3-Methylbutylamino) methyl]isoquinolin-1-yloxy}benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-(4-formylisoquinolin-1-yloxy)benzamide (Preparation 16) (100 mg, 0.34 mmol) in DMF (10 mL) was added 3-methylbutylamine (40 μL, 0.34 mmol) and 4 Å molecular sieves (200 mg). The mixture was stirred at rt for 72 h before adding NaBH4 (65 mg, 1.7 mmol). After 16 h water (1 mL) was added. Solvent was removed in vacuo and the residue purified by column chromatography (NEt3: MeOH:DCM 3:30:500) to give the title compound: RT=2.47 min; m/z (ES+)=364.0 [M+H]+.

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue purified by column chromatography (NEt3: MeOH:DCM 3:30:500)

Sources & evidence

ORD record
ord-de7b1586164c4efcb9caba60d46e8409
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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