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

HRID 1430146Notes

Reaction equation

HRID 1430146 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-amineYield 21.3%

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 401.3) (565 mg, 7 mmol), a 6N aqueous solution of HCl (3 mL) and EtOH (15 mL) is stirred for 3.5 h at 85° C., allowed to cool, quenched by addition of a saturated solution of NaHCO3 and extracted with DCM. 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→98:2) to afford 366 mg of the title compound as a yellow solid: ESI-MS: 246.1 [M+H]+; TLC: Rf=0.40 (DCM/MeOH, 9:1).

Workup

  1. temperatureto cool
  2. customquenched by addition of a saturated solution of NaHCO3
  3. extractionextracted with DCM
  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→98:2)

Sources & evidence

ORD record
ord-81a449a257b14f699994dabb24f87cac
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

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