Trifluoroacetic acid → HCID 66846903, compound

HRID 1466680Notes

Reaction equation

HRID 1466680 reaction equation
C(O)(C(F)(F)F)=O.[Br:8][C:9]1[S:10][C:11]([NH:23]C(=O)OC(C)(C)C)=[C:12]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])[N:13]=1>C(Cl)Cl.O>[Br:8][C:9]1[S:10][C:11]([NH2:23])=[C:12]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[O:21][CH3:22])[N:13]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66847104HCID 66847104, compound

Product 1

HCID 66846903HCID 66846903, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent

Procedure

TFA (4.0 mL) was added to a solution of tert-butyl 2-bromo-4-(5-chloro-2-methoxyphenyl)thiazol-5-ylcarbamate (360 mg, 0.86 mmol) in DCM (10 mL) and water (3 drops). The reaction mixture was stirred for 1.5 hours at room temperature and then evaporated to dryness. The residue was taken up into DCM and washed with sodium hydrogen carbonate (sat. aq.), water and brine, and concentrated under vacuum to give 2-bromo-4-(5-chloro-2-methoxyphenyl)thiazol-5-amine as an orange residue. LCMS (ESI) m+H=321.3. NMR (400 MHz, DMSO-d6): δ 7.36 (d, 1H); 7.34-7.32 (m, 1H); 7.10 (d, 1H); 3.83 (s, 3H).

Workup

  1. customevaporated to dryness
  2. washwashed with sodium hydrogen carbonate (sat. aq.), water and brine
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9a3882ad4d7143e9afaaf6397dafc11c
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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