Acetic Acid → HCID 178517425, compound

HRID 1262423Notes

Reaction equation

HRID 1262423 reaction equation
[F:1][C:2]1([F:24])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]3[N:19]4[C:14]([CH:15]=[N:16][C:17](S(C)(=O)=O)=[N:18]4)=[CH:13][CH:12]=3)[C:4]=2[O:3]1.[OH-].[Na+].C(O)(=[O:29])C>O1CCCC1.O>[F:1][C:2]1([F:24])[O:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([C:11]3[N:19]4[C:14]([CH:15]=[N:16][C:17]([OH:29])=[N:18]4)=[CH:13][CH:12]=3)[C:4]=2[O:3]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 667125787-(2,2-Difluoro-benzo[1,3]dioxol-4-yl)-2-methanesulfonyl-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 178517425HCID 178517425, compoundYield 91.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

7-(2,2-Difluoro-benzo[1,3]dioxol-4-yl)-2-methanesulfonyl-pyrrolo[2,1-f][1,2,4]triazine (0.410 g) was suspended in Tetrahydrofuran (2.00 mL), 5.0 M of Sodium hydroxide in Water (1.00 mL, 5.00 mmol) was added and the mixture was heated in a vial, in a block at 60° C. for 3 h. The mixture was then treated with a solution of Acetic acid (0.500 mL, 8.79 mmol) in Water (5.50 mL), generating an orange ppt. The mixture was cooled, the solids collected, washing with 10 mL water. Dry on the Buchner to afford 7-(2,2-Difluoro-benzo[1,3]dioxol-4-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol (0.310 g; Yield=78.6%). LCMS (HPLC): 0.97 min, m/z=292 (M+H); 1H-NMR (DMSO-d6): 11.97 (s, 1H), 9.10 (s, 1H), 8.38 (d, 1H, 8.0 Hz), 7.44 (d, 1H, J=7.9 Hz), 7.38 (m, 1H), 7.25 (d, 1H, J=4.8 Hz), 7.09 (d, 1H, J=4.8 Hz).

Workup

  1. temperatureThe mixture was cooled
  2. customthe solids collected
  3. washwashing with 10 mL water
  4. customDry on the Buchner

Sources & evidence

ORD record
ord-3c0bb9dc45b4494d9e7e03739a1414b0
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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