Trifluoroacetic acid → 4-(2-ethylphenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

HRID 528668Notes

Reaction equation

HRID 528668 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][O:12][C:11]2[CH:15]=[C:16]([S:19]([N:22](CC3C=CC(OC)=CC=3)[C:23]3[S:24][CH:25]=[CH:26][N:27]=3)(=[O:21])=[O:20])[CH:17]=[CH:18][C:10]1=2)[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][O:12][C:11]2[CH:15]=[C:16]([S:19]([NH:22][C:23]3[S:24][CH:25]=[CH:26][N:27]=3)(=[O:21])=[O:20])[CH:17]=[CH:18][C:10]1=2)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 897613484-(2-ethylphenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

Product 1

HCID 897616594-(2-ethylphenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamideYield 56.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-ethylphenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (400 mg, 0.77 mmol) in DCM (50 mL) was added TFA (2.0 mL) 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 ethyl acetate (2×50 mL). The combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude product which was purified by prep HPLC purification to obtain 4-(2-ethylphenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (176 mg, 56.9%) as a white solid. MS (ESI, positive ion) m/z; 402.3 (M+1). 1H NMR (400 MHz, DMSO) δ 12.51 (s, 1H), 7.42-7.38 (m, 1H), 7.33 (dt, J=4.4, 2.0 Hz, 2H), 7.29-7.24 (m, 1H), 7.21 (d, J=4.6 Hz, 1H), 7.12 (d, J=2.0 Hz, 1H), 7.08 (dd, J=8.5, 2.0 Hz, 1H), 6.77 (d, J=4.4 Hz, 1H), 6.00 (d, J=8.5 Hz, 1H), 4.34 (dd, J=10.2, 3.1 Hz, 2H), 3.74 (dt, J=7.3, 3.8 Hz, 1H), 3.51 (d, J=12.5 Hz, 1H), 2.47-2.44 (m, 2H), 1.11 (t, J=7.5 Hz, 3H).

Workup

  1. customAfter completion, the reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (20 mL)
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto obtain the crude product which
  6. customwas purified by prep HPLC purification

Sources & evidence

ORD record
ord-bd49ae269f8b4cb3a6edf660f16c558a
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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