Trifluoroacetic acid → HCID 11517063, compound

HRID 1821007Notes

Reaction equation

HRID 1821007 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])=[CH:20][C:19]=3[CH3:33])[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].FC(F)(F)C(O)=O.ClCCl.CO>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[CH:20][C:19]=3[CH3:33])[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21226129Dichloromethane methanolHCID 68894430HCID 68894430, compound

Product 1

HCID 11517063HCID 11517063, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(4-(5-(3-Cyano-4 isopropyloxyphenyl)-1,2,4-thiadiazol-3-yl)-3-methylphenyl)propanoate (110 mg, 0.23 mmol, from Step D) was treated with 20% solution of trifluoroacetic acid in dichloromethane (10 mL) for 3 h at rt. The solvents were removed under reduced pressure, residual solids dissolved in toluene and concentrated again. Pure product was isolated by a column chromatography using a Biotage 40S column (eluent: dichloromethane/methanol=9/1): 1H NMR (500 MHZ, CDCl3) δ 1.49 (d, J=6.5, 6H), 2.65 (s, 3H), 2.77 (t, J=8.0, 2H), 3.03 (t, J=8.0, 2H), 4.79 (sep, J=6.5, 1H), 7.11 (d, J=9.0, 1H), 7.21 (d, J=9.0, 1H), 7.24 (s, 1H), 7.70 (d, J=8.0, 1H), 8.17 (d, J=2.0, 1H), 8.25 (dd, J=8.0, 2.0, 1H).

Workup

  1. customThe solvents were removed under reduced pressure, residual solids
  2. dissolutiondissolved in toluene
  3. concentrationconcentrated again
  4. customPure product was isolated by a column chromatography

Sources & evidence

ORD record
ord-9e4da9d959c745148d943202156cd915
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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