Hydrochloric Acid → 5-(2-Tert-butylpyridin-4-yl)-4-methylthiazol-2-amine

HRID 1516208Notes

Reaction equation

HRID 1516208 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]2[S:15][C:14]([NH:16]C(=O)C)=[N:13][C:12]=2[CH3:20])[CH:8]=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl>CCO>[C:1]([C:5]1[CH:10]=[C:9]([C:11]2[S:15][C:14]([NH2:16])=[N:13][C:12]=2[CH3:20])[CH:8]=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59293656N-[5-(2-tert-butyl-pyridin-4-yl)-4-methyl-thiazol-2-yl]acetamide

Product 1

HCID 574170735-(2-Tert-butylpyridin-4-yl)-4-methylthiazol-2-amineYield 69.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[5-(2-tert-butyl-pyridin-4-yl)-4-methyl-thiazol-2-yl]acetamide (Step 1.3) (2 g, 7 mmol), a 6N aqueous solution of HCl (10 mL) and EtOH (50 mL) is stirred for 2 h at 85° C., allowed to cool, quenched by addition of a saturated solution of NaHCO3 and extracted with DCM/MeOH (9:1, v/v). The organic phase is washed with a saturated solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (DCM/MeOH, 1:0→96:4) to afford 1.21 g of the title compound as a yellow solid: ESI-MS: 248.1 [M+H]+; TLC: Rf=0.36 (DCM/MeOH, 9:1).

Workup

  1. temperatureto cool
  2. customquenched by addition of a saturated solution of NaHCO3
  3. extractionextracted with DCM/MeOH (9:1
  4. washThe organic phase is washed with a saturated solution of NaHCO3
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by silica gel column chromatography (DCM/MeOH, 1:0→96:4)

Sources & evidence

ORD record
ord-3ac587b7591e42c9a8bdf057dc3837c4
Source dataset
uspto-grants-2012_07
Patent number
US08227462B2

Reaction notes

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