Hydrochloric Acid → HCID 67497802, compound

HRID 1628273Notes

Reaction equation

HRID 1628273 reaction equation
[O:1]=[C:2]([NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]2[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=2)[CH:27]=1)[C@@H:3]([N:11]([CH2:19][C:20]1[N:21]=[CH:22][S:23][CH:24]=1)C(=O)OC(C)(C)C)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[H-].[Na+].[CH3:40]I.Cl>CN(C=O)C>[CH3:40][N:25]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]2[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=2)[CH:27]=1)[C:2](=[O:1])[C@@H:3]([NH:11][CH2:19][C:20]1[N:21]=[CH:22][S:23][CH:24]=1)[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69642202HCID 69642202, compound

Product 1

HCID 67497802HCID 67497802, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Amide 34.8.F (40 mg, 0.08 mmol) was dissolved in DMF, treated with NaH (3 mg, 0.08 mmol) and then MeI (5 μl, 0.08 mmol). The reaction mixture was partitioned with H2O/EtOAc. The organic layer was dried with sodium sulfate, filtered, and concentrated. The residue was purified on a prepHPLC (C18, ACN:H2O:0.1% TFA, gradient). The desired fractions were combined and partitioned with NaHCO3 (sat)/EtOAc. The organic layer was dried with sodium sulfate, filtered, and concentrated to yield 22 mg. The residue was treated with HCl (4.0 M, dioxane) and concentrated to dryness. The solid was partitioned with NaHCO3 (sat)/EtOAc. The organic layer was dried with sodium sulfate, filtered, and concentrated to yield 34.8 (15 mg). LC-MS (+esi, M+H+=429.1).

Workup

  1. customThe reaction mixture was partitioned with H2O/EtOAc
  2. dry with materialThe organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on a prepHPLC (C18, ACN:H2O:0.1% TFA, gradient)
  6. custompartitioned with NaHCO3 (sat)/EtOAc
  7. dry with materialThe organic layer was dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield 22 mg
  11. concentrationconcentrated to dryness
  12. customThe solid was partitioned with NaHCO3 (sat)/EtOAc
  13. dry with materialThe organic layer was dried with sodium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-02183891cde44617b1c51f17070dc30c
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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