Hydrochloric Acid → HCID 75202797, compound

HRID 1519131Notes

Reaction equation

HRID 1519131 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[C:9]([Cl:14])[CH:8]=2)[N:5]=[N:4][C:3]=1C(OCC)=O.[OH-].[Na+].Cl>>[Cl:14][C:9]1[CH:8]=[C:7]([NH:6][C:2]2[CH:3]=[N:4][NH:5][N:1]=2)[CH:12]=[CH:11][C:10]=1[F:13]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 82195429HCID 82195429, compound

Product 1

HCID 75202797HCID 75202797, compound

Conditions

Temperature
110 °C

Procedure

Ethyl 5-amino-1-(3-chloro-4-fluorophenyl)-1H-1,2,3-triazole-4-carboxylate 4a (120.0 mg, 0.4 mmol) was suspended in aqueous NaOH (4.00 mL of 2 M, 8.00 mmol) and the solution heated to reflux and stirred for 3 h. The solution was allowed to cool and acidified with 1M HCl and then extracted into EtOAc and the organic layer concentrated. The residue was dissolved in DMSO (2 mL) and heated to 110° C. for 3 h. The mixture was allowed to cool and purified by FractionLynx to afford the title compound I-13 as a white solid (56.8 mg, 64%). 1H NMR (500 MHz, d6-DMSO) δ 8.74 (1H, brs), 7.48-7.50 (1H, m), 7.31 (1H, s), 7.20-7.24 (1H, m), 7.10-7.13 (1H, m). MS m/z: 212.9 (M+H)+.

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux
  3. temperatureto cool
  4. extractionextracted into EtOAc
  5. concentrationthe organic layer concentrated
  6. dissolutionThe residue was dissolved in DMSO (2 mL)
  7. temperatureto cool
  8. custompurified by FractionLynx

Sources & evidence

ORD record
ord-44696fca57dd4ec3868287539326318c
Source dataset
uspto-grants-2015_07
Patent number
US09073875B2

Reaction notes

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