Trifluoroacetic acid → HCID 178490693, compound

HRID 76258Notes

Reaction equation

HRID 76258 reaction equation
[C:1]([N:5]1[CH:9]=[C:8]([CH:10](O)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)/[C:7](=[N:18]/[C:19](=[O:29])[C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=2[O:27][CH3:28])/[S:6]1)([CH3:4])([CH3:3])[CH3:2].C([SiH](CC)CC)C.[C:37]([OH:43])([C:39]([F:42])([F:41])[F:40])=[O:38]>>[F:40][C:39]([F:42])([F:41])[C:37]([OH:43])=[O:38].[CH2:10]([C:8]1=[CH:9][N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[S:6]/[C:7]/1=[N:18]\[C:19](=[O:29])[C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[O:27][CH3:28])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 178490702HCID 178490702, compound

Product 2

HCID 6422Trifluoroacetic acidYield 0.1%HCID 178490693HCID 178490693, compoundYield 25%

Conditions

Temperature
60 °C

Procedure

The product from Example 31 (20 mg, 0.05 mmol) in TFA (0.5 mL) was treated with triethylsilane (54 mg, 0.5 mmol). The mixture was heated at 60° C. for 12 hrs, solvent evaporated and the residue purified by reverse phase preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile: 0.1% aqueous trifluoroacetic acid over 8 minutes (10 minutes run time) at a flow rate of 40 mL/minute to afford 4.8 mg (25%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.61 (s, 9 H) 3.93 (s, 3 H) 4.18 (s, 2 H) 6.92 (d, J=8.90 Hz, 1 H) 7.20-7.28 (m, 1 H) 7.29-7.39 (m, 5 H) 7.78 (s, 1 H) 8.14 (d, J=2.76 Hz, 1 H); MS (DCI/NH4+) m/z 415 (M+H)+.

Workup

  1. customsolvent evaporated
  2. customthe residue purified by reverse phase preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size)

Sources & evidence

ORD record
ord-765b13135e38462aa5a6df94328e8c48
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Reaction notes

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