Hydrochloric Acid → HCID 59208447, compound

HRID 2243068Notes

Reaction equation

HRID 2243068 reaction equation
N[C:2]1[S:3][C:4]([C:16]([O:18][CH3:19])=[O:17])=[C:5]([C:7]2[N:8]([CH2:12][CH2:13][O:14][CH3:15])[CH:9]=[CH:10][N:11]=2)[N:6]=1.[ClH:20].N([O-])=O.[Na+].NC(N)=O>C(O)(=O)C.O>[Cl:20][C:2]1[S:3][C:4]([C:16]([O:18][CH3:19])=[O:17])=[C:5]([C:7]2[N:8]([CH2:12][CH2:13][O:14][CH3:15])[CH:9]=[CH:10][N:11]=2)[N:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 23668193Sodium NitriteHCID 59208395HCID 59208395, compound2×

Product 1

HCID 59208447HCID 59208447, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

Methyl 2-amino-4-[1-(2-methoxyethyl)-1H-imidazol-2-yl]-1,3-thiazole-5-carboxylate (Intermediate 55; 0.55 g, 2.2 mmol) was suspended in glacial acetic acid (20 ml) and concentrated HCl (30 ml). The solution was cooled to 0° C. and a solution of sodium nitrite in water (15 ml) was added dropwise. After stirring at 0° C. for 10 min, the reaction was slowly warmed to room temperature and stirred for 1 hour. The reaction was followed by LCMS and once complete, a solution of urea (0.25 g) in water (10 ml) was added dropwise. After stirring at room temperature for 30 min, solvent was removed under reduced pressure. The residue was partitioned with sat. NaHCO3 (aq) and EtOAc. Extraction with EtOAc (×3), drying with MgSO4 and concentrating yielded an orange oil which was used without purification (0.20 g). MS (ES) (M+H)+: 302 for C11H12ClN3O3S; NMR: 3.34 (s, 3H), 3.62 (m, 2H), 3.81 (s, 3H), 4.22 (m, 2H), 7.24 (s, 2H).

Workup

  1. temperaturethe reaction was slowly warmed to room temperature
  2. stirringstirred for 1 hour
  3. stirringAfter stirring at room temperature for 30 min
  4. customsolvent was removed under reduced pressure
  5. customThe residue was partitioned with sat. NaHCO3 (aq) and EtOAc
  6. extractionExtraction with EtOAc (×3)
  7. dry with materialdrying with MgSO4
  8. concentrationconcentrating
  9. customyielded an orange oil which
  10. customwas used without purification (0.20 g)

Sources & evidence

ORD record
ord-bdbfd30252f34f42b87fc6be95a823c1
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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