Trifluoroacetic acid → HCID 178459710, compound

HRID 2066851Notes

Reaction equation

HRID 2066851 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([NH2:28])=[CH:23][C:22]=3[F:29])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].C(N(CC)CC)C.C([NH:44][C:45]([NH:47]C(OC(C)(C)C)=O)=S)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl.[Hg]Cl>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][N:14]=[C:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([F:27])[C:24]([NH:28][C:45]([NH2:47])=[NH:44])=[CH:23][C:22]=3[F:29])[CH2:17][CH2:16]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 5193990N,N'-Di-Boc-thioureaHCID 58333444HCID 58333444, compound

Product 1

HCID 178459710HCID 178459710, compound

Reagents, catalysts & solvents 2

HCID 24182Mercurous ChlorideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 34-1 (72.5 mg, 0.18 mmol) and triethylamine (0.15 mL, 1.07 mmol) in 1 mL of DCM, was added mercury chloride (60 mg, 0.22 mmol) and di-Boc-thiourea (60 mg, 0.22 mmol). The mixture was stirred at room temperature for 4 h. It was then diluted with DCM (40 mL), filtered through a pad of celite, water (40 mL) was added to the filtrate and the layers were separated. The aqueous layer was extracted with DCM (2×40 mL), the combined extracts were dried over magnesium sulfate, filtered and the solvent was removed under vacuum to give a yellow oil. The oil was dissolved in DCM (5 mL) and TFA (2 mL, 25.96 mmol) was added. The mixture was stirred at room temperature for 1 h and then concentrated and dissolved in DCM for purification on preparative HPLC to give 36-1: LC-MS 453.1 (MH), tR=5.05 (Method 2). EC50: 1320 nM.

Workup

  1. filtrationfiltered through a pad of celite, water (40 mL)
  2. additionwas added to the filtrate
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with DCM (2×40 mL)
  5. dry with materialthe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under vacuum
  8. customto give a yellow oil
  9. stirringThe mixture was stirred at room temperature for 1 h
  10. concentrationconcentrated
  11. dissolutiondissolved in DCM for purification on preparative HPLC
  12. customto give 36-1

Sources & evidence

ORD record
ord-b9ff8d24517f41409904b190734a8d08
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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