Trifluoroacetic acid → HCID 89761996, compound

HRID 528663Notes

Reaction equation

HRID 528663 reaction equation
COC1C=CC(C[N:8]([C:33]2[S:34][CH:35]=[CH:36][N:37]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[N:20]([C:21]4[CH:31]=[CH:30][CH:29]=[CH:28][C:22]=4[O:23][CH2:24][C:25]([NH2:27])=[O:26])[CH2:19][CH2:18][O:17][C:16]=3[CH:32]=2)(=[O:11])=[O:10])=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[S:34]1[CH:35]=[CH:36][N:37]=[C:33]1[NH:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]2[N:20]([C:21]3[CH:31]=[CH:30][CH:29]=[CH:28][C:22]=3[O:23][CH2:24][C:25]([NH2:27])=[O:26])[CH2:19][CH2:18][O:17][C:16]=2[CH:32]=1)(=[O:10])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89762127HCID 89762127, compound

Product 1

HCID 89761996HCID 89761996, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-(7-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)phenoxy)acetamide (300 mg, 0.53 mmol) in DCM (30 mL) was added TFA (0.5 mL) at 0° C. The reaction mixture was stirred at ambient temperature for 5 h. After completion, the reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (50 mL) and extracted with ethyl acetate (2×50 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude material which was purified by prep HPLC purification to obtain 2-(2-(7-(N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)phenoxy)acetamide (55 mg, 13.7%) as an off white solid.

Workup

  1. customAfter completion, the reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (50 mL)
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto obtain the crude material which
  6. customwas purified by prep HPLC purification

Sources & evidence

ORD record
ord-29507ecbb10e41e18faadc475e58823c
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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