Trifluoroacetic acid → HCID 66846903, compound

HRID 529750Notes

Reaction equation

HRID 529750 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 (method 1) [M+H]+=321.3, RT=3.63 min. 1H NMR (400 MHz, DMSO-d6): δ (ppm) 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-00a86bec18974557bd56baab659e639b
Source dataset
uspto-grants-2016_05
Patent number
US09346815B2

Reaction notes

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