Trifluoroacetic acid → HCID 89761924, compound

HRID 528636Notes

Reaction equation

HRID 528636 reaction equation
COC1C=CC(C[N:8]([C:31]2[S:32][CH:33]=[CH:34][N:35]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[N:20]([C:21]4[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=4[C:23]([NH2:25])=[O:24])[CH2:19][CH2:18][O:17][C:16]=3[CH:30]=2)(=[O:11])=[O:10])=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[S:32]1[CH:33]=[CH:34][N:35]=[C:31]1[NH:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]2[N:20]([C:21]3[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=3[C:23]([NH2:25])=[O:24])[CH2:19][CH2:18][O:17][C:16]=2[CH:30]=1)(=[O:10])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89761826HCID 89761826, compound

Product 1

HCID 89761924HCID 89761924, compoundYield 3.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(7-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)benzamide (800 mg, 1.48 mmol) in DCM (15 mL) was added TFA (1.6 mL, Spectrochem) at 0° C. The reaction mixture was stirred at ambient temperature for 2 h. After completion, the reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (20 mL) and extracted with DCM (2×15 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by prep purification to obtain 2-(7-(N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)benzamide (21 mg, 3.38%) as white solid. 1H NMR (400 MHz, DMSO) δ 12.54 (s, 1H), 7.68 (s, 1H), 7.55 (t, J=7.8 Hz, 2H), 7.37 (dt, J=15.2, 7.7 Hz, 3H), 7.21 (d, J=4.6 Hz, 1H), 7.09 (d, J=1.9 Hz, 1H), 7.04 (dd, J=8.5, 2.0 Hz, 1H), 6.77 (d, J=4.4 Hz, 1H), 6.26 (d, J=8.5 Hz, 1H), 4.29-4.27 (s, 2H), 3.71-3.68 (m, 2H). LCMS (ESI) m/z; 417.5 (M+H).

Workup

  1. customAfter completion, the reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (20 mL)
  2. extractionextracted with DCM (2×15 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by prep purification

Sources & evidence

ORD record
ord-c53c4810d6dd472cb573acc1d2f66c1e
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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