Hydrochloric Acid → 4-Methyl-5-(2-(1-methylcyclopropyl)pyridin-4-yl)thiazol-2-amine

HRID 2066781Notes

Reaction equation

HRID 2066781 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:17]C(=O)C)[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]2([CH3:16])[CH2:15][CH2:14]2)[CH:8]=1.Cl>CCO>[CH3:1][C:2]1[N:3]=[C:4]([NH2:17])[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]2([CH3:16])[CH2:15][CH2:14]2)[CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86631917N-{4-methyl-5-[2-(1-methyl-cyclopropyl)-pyridin-4-yl]-thiazol-2-yl}-acetamide

Product 1

HCID 575066604-Methyl-5-(2-(1-methylcyclopropyl)pyridin-4-yl)thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-{4-methyl-5-[2-(1-methyl-cyclopropyl)-pyridin-4-yl]-thiazol-2-yl}-acetamide (Step 1.3) (34.8 mmol), a 6N aqueous solution of HCl (53 mL) and EtOH (265 mL) was stirred for 5 h at 85° C., cooled to rt and then concentrated. The residue was slowly diluted with a saturated solution of NaHCO3 and then extracted with EtOAc (3×). The combined organic phases were successively washed with a saturated solution of NaHCO3 and brine, dried (Na2SO4), filtered and concentrated. The residue was triturated with CH2Cl2 and then filtered to afford the title compound as a yellow-green solid. HPLC: t=3.55 min (method B); LC-MS: tR=1.03 min, [M+H]+ 246; TLC: Rf=0.26 (1:2 Hex/EtOAc).

Workup

  1. concentrationconcentrated
  2. additionThe residue was slowly diluted with a saturated solution of NaHCO3
  3. extractionextracted with EtOAc (3×)
  4. washThe combined organic phases were successively washed with a saturated solution of NaHCO3 and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated with CH2Cl2
  9. filtrationfiltered

Sources & evidence

ORD record
ord-816ac4350718400297c2e5cd79e2a998
Source dataset
uspto-grants-2012_10
Patent number
US08293753B2

Reaction notes

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