HCID 86655242, compound → HCID 67312003, compound

HRID 1256172Notes

Reaction equation

HRID 1256172 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]([CH2:32][CH2:33][CH3:34])=[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]([CH2:32][CH2:33][CH3:34])=[N:30][N:31]=2)[CH:7]=1

Participants

4

Reactant 1

HCID 86655242HCID 86655242, compound

Product 1

HCID 67312003HCID 67312003, compoundYield 62%

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-propyl-1,3,4-oxadiazol-2-yl)methyl)phenyl)acetamide (390 mg, 0.74 mmol) in 7M ammonium in MeOH (10 mL) was stirred in a sealed tube at 50° C. for 4 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 (195 mg, yield 62%). MS calcd for (C19H21BN4O5S): 428.3. MS found (ESI negative): (M−H)−=427.1. 1H NMR (DMSO-d6) δ (ppm): 10.0 (s, 1H), 9.12 (bs, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.37 (s, 1H), 7.17 (d, J=8.0 Hz, 1H), 7.05 (d, J=8.4 Hz, 1H), 6.36 (d, J=8.8 Hz, 1H), 6.21 (s, 1H), 4.80 (s, 2H), 4.37 (s, 2H), 2.65 (q, 2H), 1.55 (m, 2H), 0.83 (t, 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-03c6aaaec3ad4dedadfba54545343a7b
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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