Trifluoroacetic acid → [3-(5-Amino-3-methyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-phenyl]-(6-bromo-benzo[d]isothiazol-3-yl)-amine

HRID 925441Notes

Reaction equation

HRID 925441 reaction equation
C(OC(=O)[NH:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22]3[C:26]4[CH:27]=[CH:28][C:29]([Br:31])=[CH:30][C:25]=4[S:24][N:23]=3)[CH:16]=2)([CH3:14])[N:13]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C:8]1[CH2:9][O:10][CH2:11][C:12]([C:15]2[CH:16]=[C:17]([NH:21][C:22]3[C:26]4[CH:27]=[CH:28][C:29]([Br:31])=[CH:30][C:25]=4[S:24][N:23]=3)[CH:18]=[CH:19][CH:20]=2)([CH3:14])[N:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89500346HCID 89500346, compound

Product 1

HCID 71549811[3-(5-Amino-3-methyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-phenyl]-(6-bromo-benzo[d]isothiazol-3-yl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {5-[3-(6-Bromo-benzo[d]isothiazol-3-ylamino)-phenyl]-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-yl}-carbamic acid tert-butyl ester (36 mg, 0.07 mmol) in DCM (1 ml) was added at +5° C. 1 ml TFA. After 20 minutes the mixture was quenched with water and EtOH and evaporated. The residue was taken up in EtOAc/THF and washed with soda, dried with K2CO3 and purified by chromatography on silica gel (DCM/5% MeOH, then DCM/5-10% MeOH containing aq NH3) to yield the title compound.

Workup

  1. customAfter 20 minutes the mixture was quenched with water and EtOH
  2. customevaporated
  3. washwashed with soda
  4. dry with materialdried with K2CO3
  5. custompurified by chromatography on silica gel (DCM/5% MeOH

Sources & evidence

ORD record
ord-f0844b6c87ed449599c12e1f854d5bcf
Source dataset
uspto-grants-2016_03
Patent number
US09284284B2

Reaction notes

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