Trifluoroacetic acid → HCID 89761821, compound

HRID 528666Notes

Reaction equation

HRID 528666 reaction equation
COC1C=CC(C[N:8]([C:32]2[S:33][CH:34]=[CH:35][N:36]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[N:20]([C:21]4[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=4[C:23]([O:25][CH3:26])=[O:24])[CH2:19][CH2:18][O:17][C:16]=3[CH:31]=2)(=[O:11])=[O:10])=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[S:33]1[CH:34]=[CH:35][N:36]=[C:32]1[NH:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]2[N:20]([C:21]3[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=3[C:23]([O:25][CH3:26])=[O:24])[CH2:19][CH2:18][O:17][C:16]=2[CH:31]=1)(=[O:10])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89761814HCID 89761814, compound

Product 1

HCID 89761821HCID 89761821, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(7-(N-(4-methoxybenzyl)-N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)benzoate (From example 254, step 1; 1.2 g, 2.784 mmol) in DCM (40 mL) was added TFA (2.0 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 (20 mL) and the aqueous layer was extracted with DCM (2×20 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude material which was purified by combiflash column chromatography (column size: 12 g; elution: 0-50% ethyl acetate in hexane) to get methyl 2-(7-(N-(thiazol-2-yl)sulfamoyl)-2H-benzo[b][1,4]oxazin-4(3H)-yl)benzoate as a yellow solid (400 mg, 42.7%).

Workup

  1. customAfter completion, the reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (20 mL)
  2. extractionthe aqueous layer was extracted with DCM (2×20 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 combiflash column chromatography (column size: 12 g; elution: 0-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e65379b941bf4bc1932648a4500c2819
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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