Dimethylformamide → HCID 86598608, compound

HRID 915748Notes

Reaction equation

HRID 915748 reaction equation
[O:1]=[C:2]1[CH2:25][O:24][C:5]2=[CH:6][CH:7]=[C:8]3[C:12]([N:11]([CH2:13][CH:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15])[N:10]=[CH:9]3)=[C:4]2[NH:3]1.[H-].[Na+].IC.[CH3:30]N(C)C=O>O1CCCC1>[CH3:30][N:3]1[C:4]2[C:5](=[CH:6][CH:7]=[C:8]3[C:12]=2[N:11]([CH2:13][C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH3:15])[N:10]=[CH:9]3)[O:24][CH2:25][C:2]1=[O:1]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22255891HCID 22255891, compound

Product 1

HCID 86598608HCID 86598608, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 2, Step F (0.22 g, 0.64 mmol) in anhydrous tetrahydrofuran (30 mL) was added sodium hydride (60% dispersion, 28 mg, 0.70 mmol) and this mixture was stirred under a nitrogen atmosphere for 10 min. Iodomethane (99 mg, 44 uL, 0.70 mmol) was added and the mixture was stirred for 1 h followed by the addition of anhydrous dimethylformamide (20 mL); this mixture was stirred for 4 h, poured into ice water, and the solution was extracted with ethyl acetate (3×50 mL). The combined extracts were evaporated to a residue that was purified by chromatography (gradient, 20% to 50% ethyl acetate in hexane to give an oil (0.14 g, 57%): LC/MS (+APCI) m/z 361 (M+H).

Workup

  1. stirringthe mixture was stirred for 1 h
  2. stirringthis mixture was stirred for 4 h
  3. extractionthe solution was extracted with ethyl acetate (3×50 mL)
  4. customThe combined extracts were evaporated to a residue that
  5. customwas purified by chromatography (gradient, 20% to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8ef03801b4e84533874228843e4f9c41
Source dataset
uspto-grants-2007_09
Patent number
US07268131B2

Reaction notes

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