Trifluoroacetic acid → HCID 89761679, compound

HRID 528625Notes

Reaction equation

HRID 528625 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:26]=[CH:25][CH:24]=[CH:23][C:22]=4[S:27]([CH3:30])(=[O:29])=[O:28])[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>[CH3:30][S:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N:20]1[CH2:19][CH2:18][O:17][C:16]2[CH:31]=[C:12]([S:9]([NH:8][C:32]3[S:33][CH:34]=[CH:35][N:36]=3)(=[O:10])=[O:11])[CH:13]=[CH:14][C:15]1=2)(=[O:29])=[O:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89761890HCID 89761890, compound

Product 1

HCID 89761679HCID 89761679, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(4-methoxybenzyl)-4-(2-(methylsulfonyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (200 mg, 0.350 mmol) in DCM (5 mL) was added TFA (2 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 (10 mL) and extracted with DCM (2×10 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude material (71% by LCMS) that was purified by prep purification to obtain 4-(2-(methylsulfonyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (28 mg, 17.8%) as white solid. 1H NMR (400 MHz, DMSO) δ 12.51 (s, 1H), 8.07 (d, J=7.8 Hz, 1H), 7.85 (t, J=7.7 Hz, 1H), 7.77-7.54 (m, 2H), 7.19 (dd, J=15.2, 3.4 Hz, 2H), 7.08 (dd, J=8.7, 2.1 Hz, 1H), 6.77 (d, J=4.7 Hz, 1H), 6.21 (d, J=8.5 Hz, 1H), 4.42 (dt, J=10.9, 3.3 Hz, 1H), 4.34 (dd, J=10.9, 5.4 Hz, 1H), 3.61 (t, J=3.9 Hz, 2H), 3.18 (s, 3H); MS (ESI, positive ion) m/z: 452.0 (M+1).

Workup

  1. customAfter completion, the reaction mixture was quenched with saturated aqueous sodium bicarbonate solution (10 mL)
  2. extractionextracted with DCM (2×10 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto obtain the crude material (71% by LCMS) that
  6. customwas purified by prep purification

Sources & evidence

ORD record
ord-1889b4d1a6f8491c8d6449da003d9edc
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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