4-Methylmorpholine → 2,2,2-trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-(2-(methylsulfinyl)ethyl)phenyl)acetamide

HRID 1256159Notes

Reaction equation

HRID 1256159 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:9][O:8][B:7]([OH:10])[C:6]=2[CH:11]=1.CN1CCOCC1.[CH3:19][S:20]([CH2:22][CH2:23][C:24]1[CH:29]=[C:28]([NH:30][C:31](=[O:36])[C:32]([F:35])([F:34])[F:33])[CH:27]=[CH:26][C:25]=1[S:37](Cl)(=[O:39])=[O:38])=[O:21]>CC#N>[F:34][C:32]([F:33])([F:35])[C:31]([NH:30][C:28]1[CH:27]=[CH:26][C:25]([S:37](=[O:38])(=[O:39])[NH:1][C:2]2[CH:3]=[CH:4][C:5]3[CH2:9][O:8][B:7]([OH:10])[C:6]=3[CH:11]=2)=[C:24]([CH2:23][CH2:22][S:20]([CH3:19])=[O:21])[CH:29]=1)=[O:36]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-olHCID 86655228HCID 86655228, compound

Product 1

HCID 866552272,2,2-trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-(2-(methylsulfinyl)ethyl)phenyl)acetamideYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 6-amino-3H-benzo[c][1,2]oxaborol-1-ol (0.59 g, 3.9 mmol) and N-methylmorpholine (2.53 g, 25 mmol) in MeCN (70 mL) was added 2-(2-(methylsulfinyl)ethyl)-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride (1 g, crude, 2.6 mmol) in MeCN (20 mL) at 0° C., then the solution was stirred at room temperature overnight. The mixture was concentrated in vacuo, and ethyl acetate and water was added to the residue. The organic layer was dried over Na2SO4 and concentrated to give the crude product. The residue was purified by prep-HPLC (column: Luna 300×50.0 mm, 10 um; liquid phase: [A-H2O+0.05% TFA; B-MeCN] B %: 30%-60%, 25 min) to give 2,2,2-trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-(2-(methylsulfinyl)ethyl)phenyl)acetamide (0.3 g, yield 32%).

Workup

  1. concentrationThe mixture was concentrated in vacuo, and ethyl acetate and water
  2. additionwas added to the residue
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product
  6. customThe residue was purified by prep-HPLC (column: Luna 300×50.0 mm, 10 um; liquid phase: [A-H2O+0.05% TFA; B-MeCN] B %: 30%-60%, 25 min)

Sources & evidence

ORD record
ord-70b6744aa117436e94eb6b5a0ade6881
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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