Iodoethane → HCID 118159934, compound

HRID 628331Notes

Reaction equation

HRID 628331 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:19]([CH3:22])=[N:20][N:21]=3)[C:13]=2[CH:12]=[C:11]1[C:23]1[NH:27][N:26]=[CH:25][CH:24]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH2:29][CH3:30]>CN(C=O)C>[CH2:3]([N:10]1[C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:19]([CH3:22])=[N:20][N:21]=3)[C:13]=2[CH:12]=[C:11]1[C:23]1[CH:24]=[CH:25][N:26]([CH2:29][CH3:30])[N:27]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 118159527HCID 118159527, compound

Product 1

HCID 118159934HCID 118159934, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (3.3 mg, 0.082 mmol, 60% in mineral oil) was added to a solution of 6-benzyl-1-methyl-7-(1H-pyrazol-5-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (5.4 mg, 0.016 mmol, from Example 62) in DMF (0.20 mL). After 10 minutes, iodoethane (3.9 μL, 0.049 mmol, Aldrich) was introduced. After 15 minutes reaction time, the reaction was quenched with water. The product was purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN and H2O containing 0.15% NH4OH). Yield: (3.1 mg, 53%).

Workup

  1. customAfter 15 minutes reaction time
  2. customthe reaction was quenched with water
  3. customThe product was purified via preparative HPLC-MS (C18
  4. washeluting with a gradient of MeCN and H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-a07b1cf46a3544789e917234ecd6b0d8
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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