HCID 86655023, compound → HCID 58333381, compound

HRID 2066892Notes

Reaction equation

HRID 2066892 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][C:15](=[N:18][O:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]#[N:27])[CH2:22][CH2:21]2)[CH2:14][CH2:13]1.[OH:28][NH:29][C:30](=N)[CH:31]([CH3:33])[CH3:32]>C(OCC)(=O)C.[Cl-].[Cl-].[Zn+2]>[CH:31]([C:30]1[N:27]=[C:26]([N:23]2[CH2:24][CH2:25][CH:20]([O:19][N:18]=[C:15]3[CH2:16][CH2:17][N:12]([C:3]4[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:9])=[O:10])=[CH:7][C:2]=4[F:1])[CH2:13][CH2:14]3)[CH2:21][CH2:22]2)[O:28][N:29]=1)([CH3:33])[CH3:32]

Participants

5

Reactant 2

HCID 86655023HCID 86655023, compoundHCID 178449908HCID 178449908, compound

Product 1

HCID 58333381HCID 58333381, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

68b (35 mg, 0.066 mmol) and 68a (8 mg, 0.08 mmol) were combined in ethyl acetate (1 mL) and 1N ZnCl2 (80 μL, 0.08 mmol) was added dropwise. After 1 h, the solvent was evaporated. 1 mL of ethanol and 0.5 mL of concentrated HCl were added and the mixture was heated to reflux. The solvent was removed and the crude mixture was purified on preparative HPLC to give 68-1: LC-MS 480.2 (MH+), tR=5.57 (Method 5).

Workup

  1. customthe solvent was evaporated
  2. addition1 mL of ethanol and 0.5 mL of concentrated HCl were added
  3. temperaturethe mixture was heated to reflux
  4. customThe solvent was removed
  5. customthe crude mixture was purified on preparative HPLC
  6. customto give 68-1

Sources & evidence

ORD record
ord-48cb117126574275b474e7ed042c68b9
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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