3,3-Dimethylbutylamine → HCID 10337683, compound

HRID 130985Notes

Reaction equation

HRID 130985 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([CH:18]=O)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[N:6]=[CH:7][C:8]([C:11]([NH2:13])=[O:12])=[N:9][CH:10]=1.[CH3:20][C:21]([CH3:26])([CH3:25])[CH2:22][CH2:23][NH2:24].[BH4-].[Na+]>CO>[CH3:20][C:21]([CH3:26])([CH3:25])[CH2:22][CH2:23][NH:24][CH2:18][C:16]1[CH:15]=[CH:14][C:3]([O:4][C:5]2[N:6]=[CH:7][C:8]([C:11]([NH2:13])=[O:12])=[N:9][CH:10]=2)=[C:2]([F:1])[CH:17]=1

Participants

5

Reactant 3

HCID 197093,3-DimethylbutylamineHCID 4311764Sodium borohydrideHCID 597300135-(2-Fluoro-4-formylphenoxy)pyrazine-2-carboxamide

Product 1

HCID 10337683HCID 10337683, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Place 5-(2-fluoro-4-formylphenoxy)pyrazine-2-carboxamide (Example 737, Part E) (0.350 g, 1.14 mmol), 3,3-dimethylbutylamine (0.19 g, 1.41 mmol) and 3 {acute over (Å)} molecular sieves in a vial. Add methanol (9.7 mL) cap and stir overnight. Add NaBH4 (0.053 g, 1.41 mmol) and stir until the gasses stop evolving. Filter the reaction mixture, then concentrate. Purify by eluting through a 40 g ISCO® column with 6% to 30% (2.0 M NH3 in methanol) in ethyl acetate to give the title compound (0.225 g, 49%): TOF MS ES+ 347.2 (M+H)+, HRMS calcd for C18H24N4O2F 347.1883 (M+H)+, found 347.1883, time 0.53 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=10.9 min, 100% purity.

Workup

  1. filtrationFilter the reaction mixture
  2. concentrationconcentrate
  3. customPurify
  4. washby eluting through a 40 g ISCO® column with 6% to 30% (2.0 M NH3 in methanol) in ethyl acetate

Sources & evidence

ORD record
ord-2f64c9dc48e440c08153156aed80d715
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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