Isoamylamine → 2-{4-[(3-Methylbutylamino)methyl]phenoxy}thiazole-5-carboxamide

HRID 747557Notes

Reaction equation

HRID 747557 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[S:9][C:10]([C:13]([NH2:15])=[O:14])=[CH:11][N:12]=2)=[CH:5][CH:4]=1)=O.[CH2:18]([NH2:23])[CH2:19][CH:20]([CH3:22])[CH3:21].[BH4-].[Na+]>CO>[CH3:21][CH:20]([CH3:22])[CH2:19][CH2:18][NH:23][CH2:1][C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[S:9][C:10]([C:13]([NH2:15])=[O:14])=[CH:11][N:12]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7894IsoamylamineHCID 4311764Sodium borohydrideHCID 586773822-(4-Formylphenoxy)-5-thiazolecarboxamide

Product 1

HCID 117234862-{4-[(3-Methylbutylamino)methyl]phenoxy}thiazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Place 2-(4-formylphenoxy)thiazole-5-carboxamide (0.187 g, 0.755 mmol), isoamylamine (0.072 g, 0.831 mmol) and 3 Å molecular sieves in a vial. Add methanol (3.8 mL), cap and stir overnight. Add NaBH4 (0.029 g, 0.755 mmol) and stir until the gasses stop evolving. Load the reaction mixture directly onto a 25 g ISCO® pre-load column. Dry the column in a vacuum oven at room temperature. Purify by eluting through a 40 g ISCO® column with 5% (2.0 M NH3 in methanol) in ethyl acetate over 45 minutes to give the title compound: TOF MS ES+ 320.1 (M+H)+, HRMS calcd for C16H22N3O2S 320.1432 (M+H)+, found 320.1428, time 0.32 min; HPLC [YMC-Pro pack C-18 (150×4.6 mm, S-5 microm), 0.05% TFA/acetonitrile in 0.05% TFA/water at 1.0 mL/min, 10-20% over 5 min. 20-95% over 18], tR=9.7 min, 96.9% purity.

Workup

  1. customDry the column in a vacuum oven at room temperature
  2. customPurify
  3. washby eluting through a 40 g ISCO® column with 5% (2.0 M NH3 in methanol) in ethyl acetate over 45 minutes

Sources & evidence

ORD record
ord-e047d6c0b6a4425bb0f09674afd05074
Source dataset
uspto-grants-2008_07
Patent number
US07396943B2

Reaction notes

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