Trifluoroacetic acid → HCID 86717533, compound

HRID 712075Notes

Reaction equation

HRID 712075 reaction equation
[CH3:1][C:2]1[N:6](COCC[Si](C)(C)C)[N:5]=[C:4]([C:15]2[S:16][CH:17]=[CH:18][C:19]=2[NH:20][C:21](=O)OC(C)(C)C)[CH:3]=1.FC(F)(F)C(O)=O.COC(OC)N(C)C>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]2[N:5]([CH:21]=[N:20][C:19]3[CH:18]=[CH:17][S:16][C:15]=32)[N:6]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 78373Dimethylformamide dimethyl acetalHCID 86717532HCID 86717532, compound

Product 1

HCID 86717533HCID 86717533, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [2-(5-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazol-3-yl)-3-thienyl]carbamate (3.2 g, 7.8 mmol) in methylene chloride (23 mL) was added trifluoroacetic acid (23 mL). After stirring at room temperature for 5 h, the solvent was removed. The residue was dissolved in THF (40 mL) and treated with 1,1-dimethoxy-N,N-dimethylmethanamine (1.56 mL, 11.7 mmol). The resulting solution was heated at 80° C. for 1 h. The solvent was removed under reduced pressure. The crude was purified with flash chromatography (eluting with a gradient of 0-20% ethyl acetate in hexanes) to give the desired product as white solid. 1H NMR (300 MHz, CD3OD) δ 9.09 (1H, s), 7.81 (1H, d, J=5.3 Hz), 7.45 (1H, d, J=5.3 Hz), 6.60 (1H, s), 2.49 (3H, s) ppm. LCMS calculated for C9H8N3S (M+H)+: m/z=190.0. Found: 190.0.

Workup

  1. customthe solvent was removed
  2. dissolutionThe residue was dissolved in THF (40 mL)
  3. temperatureThe resulting solution was heated at 80° C. for 1 h
  4. customThe solvent was removed under reduced pressure
  5. customThe crude was purified with flash chromatography (
  6. washeluting with a gradient of 0-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e3366cc3ba5742aea21c1ec8c4ba1fd5
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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