Trifluoroacetic acid → HCID 89761907, compound

HRID 528630Notes

Reaction equation

HRID 528630 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:14](=[O:15])[CH2:13][O:12][C:11]3[CH:16]=[C:17]([S:20]([N:23](CC4C=CC(OC)=CC=4)[C:24]4[S:25][CH:26]=[CH:27][N:28]=4)(=[O:22])=[O:21])[CH:18]=[CH:19][C:10]2=3)=[C:5]([O:38][CH3:39])[CH:4]=1)#[N:2].[Al].FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:14](=[O:15])[CH2:13][O:12][C:11]3[CH:16]=[C:17]([S:20]([NH:23][C:24]4[S:25][CH:26]=[CH:27][N:28]=4)(=[O:21])=[O:22])[CH:18]=[CH:19][C:10]2=3)=[C:5]([O:38][CH3:39])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 5359268AluminumHCID 89761784HCID 89761784, compound

Product 1

HCID 89761907HCID 89761907, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolved 4-(4-cyano-2-methoxyphenyl)-N-(4-methoxybenzyl)-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (133 mg, 0.236 mmol) in 500 μl of DCM in a 10 mL rbf (wrapped with aluminum foil to exclude light) and added trifloroacetic acid (500 μl, 5.91 mmol). The solution was maintained at rt for 30 min until reaction was complete by LCMS. The reaction mixture was concentrated via rotary evaporation then purified using reverse-phase HPLC with a Waters-Xbridge C18, 19×100 mm, 10 μm column with a gradient 5-95% acetonitrile and water with 0.1% NHOH to give 4-(4-cyano-2-methoxyphenyl)-3-oxo-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (23 mg, 0.052 mmol, 22% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 3.78 (s, 3 H) 4.89 (s, 2 H) 6.39 (d, J=8.48 Hz, 1 H) 6.80 (d, J=4.47 Hz, 1 H) 7.23 (d, J=4.47 Hz, 1 H) 7.28-7.35 (m, 1 H) 7.35-7.49 (m, 1 H) 7.53-7.66 (m, 2 H) 7.80 (s, 1 H). m/z ESI 441.0 (M−H)−.

Workup

  1. concentrationThe reaction mixture was concentrated via rotary evaporation
  2. customthen purified

Sources & evidence

ORD record
ord-a160fcb86a9b4629a49eace753f500ec
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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