Trifluoroacetic acid → HCID 178482099, compound

HRID 1668497Notes

Reaction equation

HRID 1668497 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][C:13]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([NH:25][C:26]([C:28]4[S:29][CH:30]=[CH:31][CH:32]=4)=[NH:27])=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[CH:12][CH2:11]1)C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][NH:2][CH:10]1[CH2:15][CH2:14][C:13]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([NH:25][C:26]([C:28]4[S:29][CH:30]=[CH:31][CH:32]=4)=[NH:27])=[CH:22][CH:23]=3)[NH:18][CH:17]=2)=[CH:12][CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178486006HCID 178486006, compound

Product 1

HCID 178482099HCID 178482099, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of compound 124 (0.14 g, 0.310 mmol) in CH2Cl2 (5 mL) was treated with 40% TFA in CH2Cl2 (5 mL) at 0° C. and the resulting solution was stirred at same temperature for 3 h. The solvent was evaporated, crude was diluted with 10% cold NH4OH solution (25 mL) and precipitated solid was filtered off. Crude product was dried and purified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:9) to obtain compound 125 (0.095 g, 88%) as a solid. 1H NMR (DMSO-d6) δ 1.36-1.48 (m, 1H), 1.90-1.98 (m, 2H), 2.34 (s, 3H), 2.38-2.64 (m, 4H), 6.07 (brs, 1H), 6.30 (brs, 2H), 6.58 (dd, 1H, J=1.2, 8.4 Hz), 6.81 (s, 1H), 7.09 (t, 1H, J=4.2 Hz), 7.20 (d, 1H, J=2.1 Hz), 7.59 (d, 1H, J=5.1 Hz), 7.68-7.72 (m, 2H), 10.79 (s, 1H); ESI-MS (m/z, %) 351 (MH+, 100), 119(91); ESI-HRMS calculated for C20H23N4S (MH+); calculated: 351.1637; observed: 351.1638.

Workup

  1. customThe solvent was evaporated
  2. additioncrude was diluted with 10% cold NH4OH solution (25 mL)
  3. customprecipitated solid
  4. filtrationwas filtered off
  5. customCrude product was dried
  6. custompurified by column chromatography (2 M NH3 in MeOH:CH2Cl2, 1:9)

Sources & evidence

ORD record
ord-ae62d3720300487a90b10fa608d5cafb
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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