Methanesulfonic Acid → HCID 131735921, compound

HRID 2207432Notes

Reaction equation

HRID 2207432 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([B:11]([OH:13])[OH:12])[CH:10]=1)[C:5]([OH:7])=[O:6].Cl[C:15]1[N:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][N:16]=1.CS(O)(=O)=O>O1CCOCC1>[OH:12][B:11]([OH:13])[C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([NH:1][C:15]2[N:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][N:16]=2)[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 27377953-Amino-5-carboxybenzeneboronic acidHCID 27739122-Chloro-4-(trifluoromethyl)pyrimidine

Product 1

HCID 131735921HCID 131735921, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

3-Amino-5-(dihydroxyboranyl)benzoic acid (205 mg, 1.13 mmol) was added to a solution of 2-chloro-4-(trifluoromethyl)pyrimidine (203 mg, 1.11 mmol) in dioxane (3.00 mL). Methanesulfonic acid (70.0 μL, 1.08 mmol) was added to the reaction mixture and heated to reflux at 110° C. overnight. The reaction mixture was cooled to room temperature and the crude mixture was directly purified by reverse HPLC to afford 3-(dihydroxyboranyl)-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}benzoic acid. MS APCI C12H10BF3N3O4 [M+H]328. found 328.

Workup

  1. temperatureheated
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe crude mixture was directly purified by reverse HPLC

Sources & evidence

ORD record
ord-8348437442fd465bbae84c78cfd6824f
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

Loading…