Trifluoroacetic acid → HCID 68183042, compound

HRID 1615494Notes

Reaction equation

HRID 1615494 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[C:13]3[N:14]=[C:15]([C:17]4[C:18]([CH3:26])=[N:19][N:20]5[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=45)[S:16][C:12]=3[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13]3[N:14]=[C:15]([C:17]4[C:18]([CH3:26])=[N:19][N:20]5[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=45)[S:16][C:12]=3[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68182901HCID 68182901, compound

Product 1

HCID 68183042HCID 68183042, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

In a 500 mL round bottomed flask was placed 4-(4-chlorophenyl)-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-4,5,6,7-tetrahydro-1,3-benzothiazol-4-ol prepared above. The material was suspended in 1,2-dichloroethane (50 mL) and the suspension was stirred for 60 min at 90° C. To the hot solution were added triethylsilane (2 mL, 10 mmol) and trifluoroacetic acid (3 mL, 40 mmol). The mixture Was stirred for 2 days at the same temperature. The mixture was allowed to cool to rt and then concentrated under reduced pressure. The residue was diluted with EtOAc (100 mL) and then washed with a saturated aqueous solution of NaHCO3 (50 mL). The aqueous phase was extracted with EtOAc (50 mL). The combined organic phases were dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by pre-packed silica gel (40 g) column chromatography, eluting with 30% to 100% EtOAc/hexane to yield the title compound (622 mg; 91.8%) as a yellow crystalline solid. 1H NMR (400 MHz, d6-DMSO) δ ppm 8.66 (dt, 1H), 7.95 (dt, 1H), 7.33-7.37 (m, 3H), 7.16 (d, 2H), 6.96 (td, 1H), 4.27 (t, 1H), 2.84-2.93 (m, 2H), 2.56 (s, 3H), 2.15-2.21 (m, 1H), 1.77-1.88 (m, 3H).

Workup

  1. customIn a 500 mL round bottomed flask was placed
  2. stirringThe mixture Was stirred for 2 days at the same temperature
  3. temperatureto cool to rt
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was diluted with EtOAc (100 mL)
  6. washwashed with a saturated aqueous solution of NaHCO3 (50 mL)
  7. extractionThe aqueous phase was extracted with EtOAc (50 mL)
  8. dry with materialThe combined organic phases were dried over anhydrous MgSO4
  9. customInsoluble materials were removed by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by pre-packed silica gel (40 g) column chromatography
  12. washeluting with 30% to 100% EtOAc/hexane

Sources & evidence

ORD record
ord-3a612bc15bb64a06ae01d7bc46922b1e
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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