Trifluoroacetic acid → HCID 89761796, compound

HRID 528592Notes

Reaction equation

HRID 528592 reaction equation
COC1C=CC(C[N:8]([C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]3[NH:20][CH2:19][CH2:18][O:17][C:16]=3[CH:21]=2)(=[O:11])=[O:10])=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[S:23]1[CH:24]=[CH:25][N:26]=[C:22]1[NH:8][S:9]([C:12]1[CH:13]=[CH:14][C:15]2[NH:20][CH2:19][CH2:18][O:17][C:16]=2[CH:21]=1)(=[O:10])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89761436N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide2×

Product 1

HCID 89761796HCID 89761796, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (Intermediate M; 0.200 g, 0.479 mmol) was dissolved in DCM (1.597 ml) and TFA (0.923 ml, 11.98 mmol) was added. The reaction was stirred at RT for 20 minutes at which time it was concentrated in vacuo. The crude reaction was purified via 2-g SCX column (product eluted with ammonia/methanol wash) to yield N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (0.142 g, 0.478 mmol, 100% yield). m/z (ESI) 298.2 (M+H)+.

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe crude reaction
  3. customwas purified via 2-g SCX column (product eluted with ammonia/methanol wash)

Sources & evidence

ORD record
ord-04c31575ce0c484787cffbcdce16df6e
Source dataset
uspto-grants-2016_05
Patent number
US09346798B2

Reaction notes

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