Sodium borohydride → HCID 59729980, compound

HRID 130794Notes

Reaction equation

HRID 130794 reaction equation
[CH:1]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=2)=[C:5]([O:19][CH3:20])[CH:4]=1)=O.[CH3:21][CH:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][NH2:30])[CH2:24][CH2:23]1.[BH4-].[Na+]>CO>[CH3:20][O:19][C:5]1[CH:4]=[C:3]([CH2:1][NH:30][CH2:29][CH2:28][CH:25]2[CH2:26][CH2:27][CH:22]([CH3:21])[CH2:23][CH2:24]2)[CH:18]=[CH:17][C:6]=1[O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH2:14])=[O:13])=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 392350842-(4-Methylcyclohexyl)ethan-1-amineHCID 597300166-(4-Formyl-2-methoxyphenoxy)nicotinamide

Product 1

HCID 59729980HCID 59729980, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Place 6-(4-formyl-2-methoxyphenoxy)nicotinamide (Ex 414, Part B) (0.100 g, 0.367 mmol), 2-(4-methylcyclohexyl)ethylamine (0.0571 g, 0.404 mmol) and 3 {acute over (Å)} molecular sieves in a vial. Add methanol (3.6 mL), cap and stir the mixture overnight. Add NaBH4 (ca. 3-5 eq in two portions) and stir until the gasses stop evolving. Load the reaction mixture directly onto a 5 g ISCO® pre-load column. Dry the column in a vacuum oven at room temperature. Purify by eluting through a 10 g ISCO® column with 6% to 15% (2.0 M NH3 in methanol) in ethyl acetate to give 6-(2-methoxy-4-{[2-(4-methylcyclohexyl)ethylamino]methyl}phenoxy)nicotinamide. Dissolve the compound in dichloromethane (2.5 mL) and add 1 equivalent of 0.50 M methanesulfonic acid in dichloromethane. Stir the solution for a short time before concentrating to give the title compound: TOF MS ES+ 398.2 (M+H)+, HRMS calcd for C23H32N3O3 398.2444 (M+H)+, found 398.2440, time 0.52 min; Anal. Calcd for C23H31N3O3.0.5H2O: C, 57.35; H, 7.22; N, 8.36. Found: C, 57.33; H, 6.94; N, 8.34.

Workup

  1. customDry the column in a vacuum oven at room temperature
  2. customPurify
  3. washby eluting through a 10 g ISCO® column with 6% to 15% (2.0 M NH3 in methanol) in ethyl acetate

Sources & evidence

ORD record
ord-2e81ef4c6ee14667b149da35ce5850ef
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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