Trifluoroacetic acid → HCID 89761548, compound

HRID 528623Notes

Reaction equation

HRID 528623 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:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH2:28][CH2:29][O:30][CH3:31])[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>[CH3:31][O:30][CH2:29][CH2:28][O: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:32]=[C:12]([S:9]([NH:8][C:33]3[S:34][CH:35]=[CH:36][N:37]=3)(=[O:11])=[O:10])[CH:13]=[CH:14][C:15]1=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89761791HCID 89761791, compound

Product 1

HCID 89761548HCID 89761548, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(4-methoxybenzyl)-4-(2-(2-methoxyethoxyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (300 mg, 0.529 mmol) in DCM (6 mL) was added TFA (3 mL) at 0° C. The reaction mixture was stirred at ambient temperature for 2 h. After completion, the reaction mixture was quenched with saturated sodium bicarbonate solution (10 mL) and extracted with DCM (2×10 mL). The organic layer was dried over sodium sulfate and concentrated reduced pressure to obtain the crude material (36% by LCMS) that was purified by prep purification to obtain 4-(2-(2-methoxyethoxyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (38 mg, 16.1%) as white solid. 1H NMR (400 MHz, DMSO) δ 12.49 (s, 1H), 7.38-7.25 (m, 2H), 7.25-7.13 (m, 2H), 7.14-6.95 (m, 3H), 6.75 (d, J=4.6 Hz, 1H), 6.22 (d, J=8.5 Hz, 1H), 4.28 (t, J=4.3 Hz, 2H), 4.07 (dd, J=5.6, 3.5 Hz, 2H), 3.62 (t, J=4.1 Hz, 2H), 3.47 (t, J=4.5 Hz, 2H), 3.10 (s, 3H); MS (ESI, positive ion) m/z: 448.09 (M+1).

Workup

  1. customAfter completion, the reaction mixture was quenched with saturated 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 reduced pressure
  5. customto obtain the crude material (36% by LCMS) that
  6. customwas purified by prep purification

Sources & evidence

ORD record
ord-d3a64457f13d4a5687a1823447463bb3
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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