Water → HCID 58276885, compound

HRID 1478934Notes

Reaction equation

HRID 1478934 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([NH:13][C@@H:14]([CH2:29][C:30]3[N:31]=[CH:32][S:33][CH:34]=3)[C:15]([N:17]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:18][C:19]3[N:20]=[C:21]([CH3:24])[S:22][CH:23]=3)=[O:16])(=[O:12])=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].I[CH3:38].O>CN(C=O)C>[CH2:25]([N:17]([CH2:18][C:19]1[N:20]=[C:21]([CH3:24])[S:22][CH:23]=1)[C:15](=[O:16])[C@@H:14]([N:13]([CH3:38])[S:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH:2]=[CH:3][C:4]=2[CH:9]=1)(=[O:11])=[O:12])[CH2:29][C:30]1[N:31]=[CH:32][S:33][CH:34]=1)[CH:26]([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 44201083HCID 44201083, compound

Product 1

HCID 58276885HCID 58276885, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 58 (76 mg, 0.15 mmol) in DMF (1 ml) were added sodium hydride (12 mg, 0.30 mmol) and iodomethane (14 μl, 0.23 mmol). After 1 hr, water (7 ml) was added to quench the reaction. The aqueous phase was extracted with EtOAc (10 ml) and the organic layer was washed with brine (5 ml), dried over anhydrous MgSO4 and concentrated in vacuo. The crude material was purified by preparative TLC (EtOAc) to provide compound 80 (49 mg, 61%) as an oil. [M+H]+ 533.0, HPLC purity: >99%.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionThe aqueous phase was extracted with EtOAc (10 ml)
  4. washthe organic layer was washed with brine (5 ml)
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by preparative TLC (EtOAc)

Sources & evidence

ORD record
ord-b0ee403483024c52b14a30ba991df238
Source dataset
uspto-grants-2016_08
Patent number
US09403789B2

Reaction notes

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