Hydrochloric Acid → HCID 57506655, compound

HRID 1430119Notes

Reaction equation

HRID 1430119 reaction equation
Cl.[N:2]1([C:7]2[N:12]=[C:11]([C:13]3[S:17][C:16]([NH:18]C(=O)C)=[N:15][C:14]=3[CH3:22])[CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][N:4]=[CH:3]1>C(O)C>[N:2]1([C:7]2[N:12]=[C:11]([C:13]3[S:17][C:16]([NH2:18])=[N:15][C:14]=3[CH3:22])[CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][N:4]=[CH:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57417075HCID 57417075, compound

Product 1

HCID 57506655HCID 57506655, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Conc. HCl (0.3 ml) is added to a suspension of N-[5-(6-imidazol-1-yl-pyridin-2-yl)-4-methyl-thiazol-2-yl]-acetamide (30 mg) in ethanol (2 ml) at room temperature. The mixture is heated at reflux for 7 hours. Following cooing the mixture is partitioned between saturated aqueous NaHCO3 and CH2Cl2 containing 10% methanol and extracted a further 4×CH2Cl2 containing 10% methanol. Evaporation of the organic layers gives the title compound as a beige solid. 1H nmr (d4-methanol, 400 MHz) 8.50 (s, 1H), 7.94-7.86 (m, 2H), 7.45-7.37 (m, 2H), 7.16 (s, 1H), 2.51 (s, 3H).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 7 hours
  3. customis partitioned between saturated aqueous NaHCO3 and CH2Cl2 containing 10% methanol
  4. extractionextracted a further 4×CH2Cl2 containing 10% methanol
  5. customEvaporation of the organic layers

Sources & evidence

ORD record
ord-11df96045ad141a8b83afa205baa2122
Source dataset
uspto-grants-2015_01
Patent number
US08940771B2

Reaction notes

Loading…