Sodium borohydride → 5-{4-[(3-Ethylpentylamino)methyl]phenoxy}thiophene-2-carboxamide

HRID 747553Notes

Reaction equation

HRID 747553 reaction equation
CC(C)CCN[CH2:6][C:7]1[CH:21]=[CH:20][C:10]([O:11][C:12]2[S:16][C:15]([C:17]([NH2:19])=[O:18])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1.[CH2:23]([CH:25]([CH2:29][CH3:30])[CH2:26][CH2:27][NH2:28])[CH3:24].[BH4-].[Na+]>CO>[CH2:23]([CH:25]([CH2:29][CH3:30])[CH2:26][CH2:27][NH:28][CH2:6][C:7]1[CH:21]=[CH:20][C:10]([O:11][C:12]2[S:16][C:15]([C:17]([NH2:19])=[O:18])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1)[CH3:24]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 103138305-{4-[(3-Methylbutylamino)methyl]phenoxy}thiophene-2-carboxamideHCID 157055453-Ethylpentan-1-amine

Product 1

HCID 100205505-{4-[(3-Ethylpentylamino)methyl]phenoxy}thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Place 5-(4-formylphenoxy)thiophene-2-carboxamide (Example 10, Part C) (0.235 g, 0.948 mmol), 3-ethylpentylamine (Part B) (0.115 g, 0.996 mmol) and 3 Å molecular sieves in a vial. Add methanol (4.7 mL), cap and stir overnight. Add NaBH4 (0.0359 g, 0.948 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% to 20% (2.0 M NH3 in methanol) in ethyl acetate over 45 minutes to give the title compound: TOF MS ES+ 347.2 (M+H)+, HRMS calcd for C19H27N2O2S 347.1793 (M+H)+, found 347.1799, time 0.38 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=12.4 min, 100% 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% to 20% (2.0 M NH3 in methanol) in ethyl acetate over 45 minutes

Sources & evidence

ORD record
ord-fd8e6a1b195a452f97a795de29f890a6
Source dataset
uspto-grants-2008_07
Patent number
US07396943B2

Reaction notes

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