HCID 86655238, compound → HCID 67310994, compound

HRID 1256168Notes

Reaction equation

HRID 1256168 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][C:27]2[O:28][C:29]([CH3:32])=[N:30][N:31]=2)[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][C:27]2[O:28][C:29]([CH3:32])=[N:30][N:31]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 86655238HCID 86655238, compound

Product 1

HCID 67310994HCID 67310994, compoundYield 37.5%

Reagents, catalysts & solvents 2

HCID 223AmmoniumSolventHCID 887MethanolSolvent

Procedure

A solution of 2,2,2-trifluoro-N-(4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-3-((5-methyl-1,3,4-oxadiazol-2-yl)methyl)phenyl)acetamide (300 mg, 0.60 mmol) in 7M ammonium in MeOH (10 mL) was stirred in a sealed tube at 50° C. for 16 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 (90 mg, yield 37%). MS calcd for (C14H17BN4O5S): 400.2. MS found (ESI negative): (M−H)−=399.1. 1H NMR (DMSO-d6) δ (ppm): 10.0 (s, 1H), 9.20 (bs, 1H), 7.56 (d, J=8.8 Hz, 1H), 7.42 (s, 1H), 7.22 (d, J=8.4 Hz, 1H), 7.11 (d, J=8.4 Hz, 1H), 6.41 (d, J=8.4 Hz, 1H), 6.26 (s, 1H), 4.85 (s, 2H), 4.41 (s, 2H), 2.39 (s, 3H)

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-f38233a5ca1b433ba7fb433e7ada990c
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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