Ethanol → HCID 10044033, compound

HRID 273316Notes

Reaction equation

HRID 273316 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][C:11](=[O:15])[N:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[CH:8]=[C:7]1[C:22]([NH2:24])=O.N1C=CC=CC=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.CCO>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][C:11](=[O:15])[N:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]=2[CH:8]=[C:7]1[C:22]#[N:24]

Participants

6

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 10384967HCID 10384967, compound

Product 1

HCID 10044033HCID 10044033, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of Example 32 (200 mg, 0.53 mmol) in DCM (2 ml) was treated with pyridine (0.11 ml 1.06 mmol) followed, after a few minutes, by TFAA (0.09 ml, 0.64 mmol). The reaction was stirred at r.t. for 15 minutes. EtOH (2 ml) was added and stirred for 5 minutes prior to removal of solvents in vacuo. The residue was dissolved in DCM (15 ml) and washed with copper(II) sulfate (2×10 ml), dried (MgSO4) and concentrated in vacuo to give the title compound (175 mg, 92%). δH (d3-MeOD) 7.87 (1H, d, J 9.7 Hz), 7.55-7.43 (3H, m), 7.32-7.23 (4H, m), 7.18 (1H, s), 7.06-7.03 (1H, m), 6.55 (1H, d, J 9.7 Hz), 6.25 (1H, s), 5.45 (2H, s). LCMS (ES+) RT 3.43 minutes, 360 [35Cl]:362 [37Cl] 3:1 (M+H+).

Workup

  1. stirringstirred for 5 minutes
  2. customto removal of solvents in vacuo
  3. dissolutionThe residue was dissolved in DCM (15 ml)
  4. washwashed with copper(II) sulfate (2×10 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-871573abe8944c2ab0fad86c3cdfaab1
Source dataset
uspto-grants-2008_11
Patent number
US07456286B2

Reaction notes

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