Methanol → 4-Methyl-5-(4-methyl-piperazine-1-sulfonyl)-thiazol-2-ylamine

HRID 1685536Notes

Reaction equation

HRID 1685536 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[S:15][C:14]([NH:16]C(=O)C)=[N:13][CH:12]=2)(=[O:10])=[O:9])[CH2:4][CH2:3]1.[CH3:20]O>Cl>[CH3:20][C:12]1[N:13]=[C:14]([NH2:16])[S:15][C:11]=1[S:8]([N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 887MethanolHCID 42560673Acetamide, N-[5-[(4-methyl-1-piperazinyl)sulfonyl]-2-thiazolyl]-

Product 1

HCID 639461724-Methyl-5-(4-methyl-piperazine-1-sulfonyl)-thiazol-2-ylamine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-[5-(4-methylpiperazine-1-sulfonyl)-thiazol-2-yl]-acetamide (1 g, 3.1 mmol) in methanol (5 mL) and 6 N hydrochloric acid (5 mL) was heated in a microwave oven (4×5 min at 80° C.). The reaction mixture was partly evaporated to remove most of the methanol, and the residue was washed with DCM (10 mL). The water phase was isolated, and the pH adjusted to 8-9. Extraction with DCM (3×25 mL), drying over anhydrous magnesium sulphate, and evaporation in vacuo gave white crystals of 4-methyl-5-(4-methyl-piperazine-1-sulfonyl)-thiazol-2-ylamine. Yield: 0.53 g (61%). 1H-NMR (CDCl3): δ 5.46 (m, 2H); 3.18 (m, 4H); 2.51 (m, 4H); 2.45 (s, 3H); 2.31 (s, 3H).

Workup

  1. customThe reaction mixture was partly evaporated
  2. customto remove most of the methanol
  3. washthe residue was washed with DCM (10 mL)
  4. customThe water phase was isolated
  5. extractionExtraction with DCM (3×25 mL)
  6. dry with materialdrying over anhydrous magnesium sulphate, and evaporation in vacuo

Sources & evidence

ORD record
ord-8ce18b69026c4a3ebebdc9db287193f0
Source dataset
uspto-grants-2012_04
Patent number
US08148412B2

Reaction notes

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