Ammonia hydroxide → HCID 67311505, compound

HRID 1256175Notes

Reaction equation

HRID 1256175 reaction equation
[F:1][C:2]1[C:11]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:22]C(=O)C(F)(F)F)=[CH:18][C:17]=2[CH2:29][C:30](OC)=[O:31])(=[O:15])=[O:14])=[CH:10][C:5]2[B:6]([OH:9])[O:7][CH2:8][C:4]=2[CH:3]=1.[OH-].[NH3:35]>CO>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([S:13](=[O:14])(=[O:15])[NH:12][C:11]2[C:2]([F:1])=[CH:3][C:4]3[CH2:8][O:7][B:6]([OH:9])[C:5]=3[CH:10]=2)=[C:17]([CH2:29][C:30]([NH2:35])=[O:31])[CH:18]=1

Participants

4

Reactant 2

HCID 21862953Ammonia hydroxideHCID 86655215HCID 86655215, compound

Product 1

HCID 67311505HCID 67311505, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To the solution of methyl 2-(2-(N-(5-fluoro-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)-5-(2,2,2-trifluoroacetamido)phenyl)acetate (480 mg, 1 mmol) in methanol (5 ml), added ammonia hydroxide (2 ml), heated at 100° C. in a sealed tube overnight. The result mixture was concentrated, then dissolved in DMSO and purified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column). The title compound was obtained as yellow solid. MS calcd for (C15H15BN3O5FS): 379.17. MS found (ESI negative): (M−H)−=378.1. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.64 (s, 1H), 9.20 (bs, 1H), 7.53 (d, J=8 Hz, 1H), 7.34 (s, 1H), 7.25 (d, J=8.8 Hz, 1H), 7.13 (d, J=10.4 Hz, 1H), 7.04 (s, 1H), 6.45 (d, J=2 Hz, 1H), 6.29 (dd, J=8.8 Hz, 1H), 4.82 (s, 2H).

Workup

  1. concentrationThe result mixture was concentrated
  2. dissolutiondissolved in DMSO
  3. custompurified by prep HPLC (SunFire Prep C18 OBD 5 uM 30×50 mm column)

Sources & evidence

ORD record
ord-bd27e41edb914fbb96f688f6f5e20351
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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