Trifluoroacetic acid → HCID 59128672, compound

HRID 1991096Notes

Reaction equation

HRID 1991096 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([S:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:18]=[C:13]3[C:12]([C:26]3[CH:27]=[N:28][N:29](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:30]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O.[SiH](C(C)C)(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([S:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:18]=[C:13]3[C:12]([C:26]3[CH:27]=[N:28][NH:29][CH:30]=3)=[CH:11]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 138754Silane, tris(1-methylethyl)-HCID 516892Sodium BicarbonateHCID 59128656HCID 59128656, compound

Product 1

HCID 59128672HCID 59128672, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 6 (346 mg, 0.51 mmol), CH2Cl2 (4.4 mL), CF3COOH (410 μL), H2O (41 μL) and i-Pr3SiH (207 μL) were stirred for 0.5 h then added dropwise to a stirred mixture of CH2Cl2/sat. aq. NaHCO3. The layers were separated and the aqueous phase extracted with more CH2Cl2 (3×), dried (MgSO4) and concentrated. The residue was separated by means of silicagel chromatography (SGC) using AcOEt:hexane as eluent in gradient up to 65:35 (v/v) to give 7 as a white solid (160 mg, 72%); 1H NMR (400 MHz, CDCl3+6 drops CD3OD) δ 7.10-7.28 (m, 5H), 7.47 (t, J=7.7 Hz, 2H), 7.56 (t, J=7.5 Hz, 1H), 7.75 (s, 2H), 7.78 (s, 1H), 8.01 (d, J=2.1 Hz, 1H), 8.13 (d, J=1.4 Hz, 1H), 8.16 (s, 1H), 8.42 (d, J=2.0 Hz, 1H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase extracted with more CH2Cl2 (3×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was separated by means of silicagel chromatography (SGC)

Sources & evidence

ORD record
ord-a09d3522faa9492f968d566a21564290
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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