Ammonium → HCID 53234372, compound

HRID 1256106Notes

Reaction equation

HRID 1256106 reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](=[O:25])(=[O:24])[NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)=[C:8]([CH2:26][CH2:27][F:28])[CH:7]=1)=O.[NH4+]>CO>[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:13][C:14]2[CH:15]=[CH:16][C:17]3[CH2:21][O:20][B:19]([OH:22])[C:18]=3[CH:23]=2)(=[O:24])=[O:25])=[C:8]([CH2:26][CH2:27][F:28])[CH:7]=1

Participants

4

Reactant 2

HCID 223AmmoniumHCID 86655214HCID 86655214, compound

Product 1

HCID 53234372HCID 53234372, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 2,2,2-trifluoro-N-(3-(2-fluoroethyl)-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetamide (210 mg, 0.47 mmol) and 7M ammonium in MeOH (10 mL) in 10 mL of MeOH was stirred in a sealed tube at 60° C. for 2 hours. After concentrated, the crude mixture was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column) to give the title compound as a yellow solid (87 mg). MS calcd for (C15H16BFN2O4S): 350.1. MS found (ESI negative): (M−H)−=349.1. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.05 (s, 1H), 9.2 (bs, 1H), 7.57 (d, J=8.4 Hz, 1H), 7.42 (d, J=2 Hz, 2H), 7.22 (d, J=8 Hz, 1H), 7.12 (dd, J=8, 2 Hz, 1H), 6.46 (d, J=2 Hz, 1H), 6.40 (dd, J=8.4, 2 Hz, 1H), 5.5 (bs, 2H), 4.86 (s, 2H), 4.59 (dt, J=48, 6.4 Hz, 2H), 4.23 (dt, J=23, 6 Hz, 2H).

Workup

  1. concentrationAfter concentrated
  2. customthe crude mixture was purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Sources & evidence

ORD record
ord-764da36954474b108114b2fe4907e77f
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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