HCID 86655240, compound → HCID 67174085, compound

HRID 1256170Notes

Reaction equation

HRID 1256170 reaction equation
[CH2:1]([C:3]1[O:7][C:6]([CH2:8][C:9]2[CH:10]=[C:11]([NH:29]C(=O)C(F)(F)F)[CH:12]=[CH:13][C:14]=2[S:15](=[O:28])(=[O:27])[NH:16][C:17]2[CH:18]=[CH:19][C:20]3[CH2:24][O:23][B:22]([OH:25])[C:21]=3[CH:26]=2)=[N:5][N:4]=1)[CH3:2]>[NH4+].CO>[NH2:29][C:11]1[CH:12]=[CH:13][C:14]([S:15]([NH:16][C:17]2[CH:18]=[CH:19][C:20]3[CH2:24][O:23][B:22]([OH:25])[C:21]=3[CH:26]=2)(=[O:27])=[O:28])=[C:9]([CH2:8][C:6]2[O:7][C:3]([CH2:1][CH3:2])=[N:4][N:5]=2)[CH:10]=1

Participants

4

Reactant 1

HCID 86655240HCID 86655240, compound

Product 1

HCID 67174085HCID 67174085, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 223AmmoniumSolventHCID 887MethanolSolvent

Procedure

A solution of N-(3-((5-ethyl-1,3,4-oxadiazol-2-yl)methyl)-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)-2,2,2-trifluoroacetamide (390 mg, 0.76 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 (204 mg, yield 64%). MS calcd for (C18H19BN4O5S): 414.2, MS found (ESI negative): (M−H)−=413.1. 1H NMR (DMSO-d6) δ (ppm): 10.0 (s, 1H), 9.16 (bs, 1H), 7.56 (d, J=8.8 Hz, 1H), 7.42 (s, 1H), 7.22 (d, J=8.0 Hz, 1H), 7.11 (d, J=8.4 Hz, 1H), 6.42 (d, J=8.8 Hz, 1H), 6.26 (s, 1H), 4.85 (s, 2H), 4.42 (s, 2H), 2.75 (q, 2H), 1.19 (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-c56b15c3e1c8401fb95827d3a50cfc2a
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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