Trifluoroacetic acid → HCID 18511561, compound

HRID 1819794Notes

Reaction equation

HRID 1819794 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[S:16][C:17]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:18]=3[N:19]=2)[CH:11]=[C:10]([Cl:25])[CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>>[Cl:25][C:10]1[CH:9]=[C:8]([NH2:7])[CH:13]=[C:12]([O:14][C:15]2[S:16][C:17]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:18]=3[N:19]=2)[CH:11]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67242037HCID 67242037, compound

Product 1

HCID 18511561HCID 18511561, compoundYield 88.5%

Procedure

To [3-chloro-5-(5-chloro-benzothiazol-2-yloxy)-phenyl]-carbamic acid tert-butyl ester (263, 1.17 g, 2.85 mmol) was added trifluoroacetic acid. The mixture was stirred at ambient temperature for 5 h, at which time TLC showed there was no starting material remained. The mixture was concentrated to dryness under reduced pressure, dissolved in EtOAc. The organic solution was washed with 1N NaOH, washed twice with a brine solution, dried over Na2SO4 and concentrated. The residue was purified by chromatography with CH2Cl2 to give 785 mg of product. 1H NMR (400 MHz, DMSO-d6) δ 7.98 (d, J=8.6 Hz, 1H), 7.82 (d, J=2.0 Hz, 1H), 6.62 (t, J=1.9 Hz, 1H), 6.58 (t, J=1.8 Hz, 1H), 6.50 (t, J=1.9 Hz, 1H), 5.81 (s, 2H). MS (EI): m/z 311 (M+H).

Workup

  1. concentrationThe mixture was concentrated to dryness under reduced pressure
  2. dissolutiondissolved in EtOAc
  3. washThe organic solution was washed with 1N NaOH
  4. washwashed twice with a brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography with CH2Cl2

Sources & evidence

ORD record
ord-e9e02b0c6a6e4efb91df434afee3336e
Source dataset
uspto-grants-2009_10
Patent number
US07601841B2

Reaction notes

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