Trifluoroacetic acid → HCID 89761981, compound

HRID 528618Notes

Reaction equation

HRID 528618 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][O:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=1[N:20]1[C:25](=[O:26])[CH2:24][O:23][C:22]2[CH:27]=[C:28]([S:31]([N:34](CC3C=CC(OC)=CC=3)[C:35]3[S:36][CH:37]=[CH:38][N:39]=3)(=[O:33])=[O:32])[CH:29]=[CH:30][C:21]1=2>C(Cl)Cl>[CH3:8][O:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:17])[F:18])[CH:13]=[CH:12][C:11]=1[N:20]1[C:25](=[O:26])[CH2:24][O:23][C:22]2[CH:27]=[C:28]([S:31]([NH:34][C:35]3[S:36][CH:37]=[CH:38][N:39]=3)(=[O:32])=[O:33])[CH:29]=[CH:30][C:21]1=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89761995HCID 89761995, compound

Product 1

HCID 89761981HCID 89761981, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 25-mL round bottom flask was dissolved 4-(2-methoxy-4-(trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide in 4 mL of DCM then treated with TFA (2.384 mL, 30.9 mmol). After 30 min the reaction mixture was concentrated under reduced pressure and purified by MPLC (ISCO) with DCM:MeOH 100:0 to 90:10 to afforded 4-(2-methoxy-4-(trifluoromethyl)phenyl)-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H benzo[b][1,4]oxazine-7-sulfonamide (250 mg, 0.515 mmol, 83.0% yield from INTERMEDIate AB2) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.81 (s, 3 H) 4.91 (s, 2 H) 6.41 (d, J=8.41 Hz, 1 H) 6.83 (d, J=4.60 Hz, 1 H) 7.26 (d, J=4.60 Hz, 1 H) 7.34 (dd, J=8.36, 2.01 Hz, 1 H) 7.38 (d, J=1.96 Hz, 1 H) 7.51 (d, J=8.12 Hz, 1 H) 7.55-7.65 (m, 2 H) 12.75 (br. s., 1 H). m/z (ESI) 486.0 (M+H)+.

Workup

  1. concentrationAfter 30 min the reaction mixture was concentrated under reduced pressure
  2. custompurified by MPLC (ISCO) with DCM:MeOH 100:0 to 90:10

Sources & evidence

ORD record
ord-736bb5c801cf4e8ba875a94413bcce09
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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