Hydrochloric Acid → 1-(1,3-oxazol-2-ylmethyl)-1H-indazol-5-amine

HRID 1162237Notes

Reaction equation

HRID 1162237 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:14][C:15]1[O:16][CH:17]=[CH:18][N:19]=1)[N:9]=[CH:8]2)([O-])=O.Cl[Sn]Cl.[OH-].[Na+]>C(O)C>[O:16]1[CH:17]=[CH:18][N:19]=[C:15]1[CH2:14][N:10]1[C:11]2[C:7](=[CH:6][C:5]([NH2:2])=[CH:13][CH:12]=2)[CH:8]=[N:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 68618801HCID 68618801, compound

Product 1

HCID 686189121-(1,3-oxazol-2-ylmethyl)-1H-indazol-5-amineYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Concentrated HCl (2.5 mL) was added to a solution of 5-nitro-1-(1,3-oxazol-2-ylmethyl)-1H-indazole (456 mg, 1.87 mmol) and SnCl2 (1.42 g, 7.47 mmol) in ethanol (10 mL) and the mixture was heated at 50° C. for 4 hours. The mixture was cooled down, neutralized to pH 8 with 2N sodium hydroxide and extracted with ethyl acetate. The residue is purified on silica gel (EtOAc) to give 1-(1,3-oxazol-2-ylmethyl)-1H-indazol-5-amine (182 mg, 46%); NMR spectrum (CDCl3) 5.55 (s, 2H), 6.79 (d, 1H), 6.86 (s, 1H), 7.00 (s, 1H), 7.24 (d, 1H), 7.50 (s, 1H), 7.77 (s, 1H); Mass spectrum MH+ 215.

Workup

  1. temperatureThe mixture was cooled down
  2. extractionextracted with ethyl acetate
  3. customThe residue is purified on silica gel (EtOAc)

Sources & evidence

ORD record
ord-869171e8d1cf4f028aa6dc15b9ff997d
Source dataset
uspto-grants-2010_10
Patent number
US07820683B2

Reaction notes

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