Trifluoroacetic acid → HCID 89761866, compound

HRID 528656Notes

Reaction equation

HRID 528656 reaction equation
[OH:1][C:2]([CH3:40])([CH3:39])[CH2:3][O:4][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.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:1][C:2]([CH3:40])([CH3:39])[CH2:3][O:4][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:22])=[O:23])[CH:19]=[CH:20][C:12]1=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89761565HCID 89761565, compound

Product 1

HCID 89761866HCID 89761866, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-(2-hydroxy-2-methylpropoxy)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (600 mg, 0.585 mmol) in DCM (5 mL) was added TFA (1.4 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 the crude material which was purified by prep HPLC purification to obtain 4-(2-(2-hydroxy-2-methylpropoxy)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (120 mg, 26.0%) as a white solid. m/z (ESI) 461.8 (M+H)+. 1H NMR (400 MHz, DMSO) δ 12.50 (s, 1H), 7.38-7.24 (m, 2H), 7.20 (d, J=4.6 Hz, 1H), 7.16-6.95 (m, 4H), 6.76 (d, J=4.3 Hz, 1H), 6.23-6.00 (m, 1H), 4.46 (s, 1H), 4.31 (d, J=3.9 Hz, 2H), 3.61-3.58 (m, 4H), 0.83 (s, 6H).

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 the crude material which
  6. customwas purified by prep HPLC purification

Sources & evidence

ORD record
ord-9eb5b46eea744d429b152acffdba718e
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

Loading…