Trifluoroacetic acid → HCID 60054676, compound

HRID 1792879Notes

Reaction equation

HRID 1792879 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:43])[CH2:14][N:15]1[CH2:34][C@@H:33]([C:35]2[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=2)[C@:17]2([N:21]([CH3:22])[C:20](=[O:23])[N:19]([C:24]3[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=3)[C:18]2=[O:32])[CH2:16]1)(C)(C)C>C(Cl)Cl>[C:41]([C:38]1[CH:37]=[CH:36][C:35]([C@H:33]2[C@:17]3([N:21]([CH3:22])[C:20](=[O:23])[N:19]([C:24]4[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=4)[C:18]3=[O:32])[CH2:16][N:15]([CH2:14][C:13]([OH:43])=[O:12])[CH2:34]2)=[CH:40][CH:39]=1)#[N:42]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69586070HCID 69586070, compound

Product 1

HCID 60054676HCID 60054676, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4.8 ml, 59 mmol) was added to a solution of Example 63 (1.56 g, 2.95 mmol) in DCM (40 ml). The solution was refluxed for 3 h. It was then concentrated in vacuo and partitioned between EtOAc/aqueous NH4OH. The aqueous layer was acidified to pH=2 with SO2. The white precipitate was separated by filtration. The aqueous layer was extracted with DCM and concentrated to give white crystals which where combined with the precipitated solid to give, after drying, the above-titled compound (1.04 g), mp=220° C.

Workup

  1. temperatureThe solution was refluxed for 3 h
  2. concentrationIt was then concentrated in vacuo
  3. custompartitioned between EtOAc/aqueous NH4OH
  4. customThe white precipitate was separated by filtration
  5. extractionThe aqueous layer was extracted with DCM
  6. concentrationconcentrated
  7. customto give white crystals which where
  8. customto give
  9. customafter drying

Sources & evidence

ORD record
ord-2179b14edb1d4017bd86105da61999c7
Source dataset
uspto-grants-2006_07
Patent number
US07078420B2

Reaction notes

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