4-Methylmorpholine → HCID 86655210, compound

HRID 1256087Notes

Reaction equation

HRID 1256087 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.[O:19]=[C:20]([CH3:40])[CH2:21][CH2:22][C:23]1[CH:28]=[C:27]([NH:29][C:30](=[O:35])[C:31]([F:34])([F:33])[F:32])[CH:26]=[CH:25][C:24]=1[S:36](Cl)(=[O:38])=[O:37]>CC#N>[F:34][C:31]([F:32])([F:33])[C:30]([NH:29][C:27]1[CH:26]=[CH:25][C:24]([S:36](=[O:37])(=[O:38])[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:23]([CH2:22][CH2:21][C:20](=[O:19])[CH3:40])[CH:28]=1)=[O:35]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 37701876-Aminobenzo(c)(1,2)oxaborol-1(3H)-olHCID 86655211HCID 86655211, compound

Product 1

HCID 86655210HCID 86655210, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 6-amino-3H-benzo[c][1,2]oxaborol-1-ol (0.37 g, 2 mmol) and NMM (0.76 g, 7 mmol) in CH3CN (50 mL) was added a solution of 2-(3-oxobutyl)-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride (0.9 g, 2 mmol) in CH3CN (30 mL) dropwise at 0° C. The reaction mixture was stirred at room temperature for 2 hrs, then the reaction mixture was concentrated in vacuo, the residue was diluted with water and extracted with EtOAc, the organics was dried over Na2SO4, concentrated to give the crude product, the crude was purified by pre-HPLC (column: Luna 300×50.0 mm, 10 um; liquid phase: [A-H2O+0.05% TFA; B-MeCN] B %: 24%-51%, 23 min) to give 2,2,2-trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-(3-oxobutyl)phenyl)acetamide (0.5 g, yield 42%) as yellow solid.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with EtOAc
  4. dry with materialthe organics was dried over Na2SO4
  5. concentrationconcentrated
  6. customto give the crude product
  7. customthe crude was purified by pre-HPLC (column: Luna 300×50.0 mm, 10 um; liquid phase: [A-H2O+0.05% TFA; B-MeCN] B %: 24%-51%, 23 min)

Sources & evidence

ORD record
ord-25e25ef2315b46ff8d5b5d4dfbe57659
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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