Trifluoroacetic acid → HCID 89761835, compound

HRID 528658Notes

Reaction equation

HRID 528658 reaction equation
O[C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][O:14][C:13]2[CH:17]=[C:18]([S:21]([N:24](CC3C=CC(OC)=CC=3)[C:25]3[S:26][CH:27]=[CH:28][N:29]=3)(=[O:23])=[O:22])[CH:19]=[CH:20][C:12]1=2)([CH3:4])[CH3:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:3]=[C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][O:14][C:13]2[CH:17]=[C:18]([S:21]([NH:24][C:25]3[S:26][CH:27]=[CH:28][N:29]=3)(=[O:23])=[O:22])[CH:19]=[CH:20][C:12]1=2)[CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89761688HCID 89761688, compound

Product 1

HCID 89761835HCID 89761835, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-(2-hydroxypropan-2-yl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (300 mg, 0.543 mmol) in DCM (5 mL) was added TFA (0.4 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 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 crude material (47% by LCMS) that was purified by prep HPLC to obtain 4-(2-(prop-1-en-2-yl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide as a white solid (45 mg, 20.0%). MS (ESI, positive ion) m/z; 414.1 (M+1). 1H NMR (400 MHz, DMSO) δ 12.51 (s, 1H), 7.50-7.26 (m, 4H), 7.21 (d, J=4.6 Hz, 1H), 7.16-6.94 (m, 1H), 6.77 (d, J=4.5 Hz, 1H), 6.23 (d, J=8.4 Hz, 1H), 5.10 (s, 1H), 4.96 (s, 1H), 4.41-4.08 (m, 2H), 3.52 (d, J=11.7 Hz, 2H), 1.96 (s, 3H).

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 under reduced pressure
  5. customto obtain crude material (47% by LCMS) that
  6. customwas purified by prep HPLC

Sources & evidence

ORD record
ord-df8b97715efd4d16b4edab476da9a9c2
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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