Iodoethane → HCID 118159856, compound

HRID 628332Notes

Reaction equation

HRID 628332 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[C:18]2[C:13](=[N:14][C:15]([N:19](C(OC(C)(C)C)=O)[NH:20][C:21](OC(C)(C)C)=O)=[CH:16][CH:17]=2)[CH:12]=[C:11]1[C:35]1[N:36]=[CH:37][N:38]([C:40](C2C=CC=CC=2)([C:47]2C=CC=CC=2)C2C=CC=CC=2)[CH:39]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH2:60]C>CN(C=O)C>[CH2:3]([N:10]1[C:18]2[CH:17]=[CH:16][C:15]3[N:14]([C:21]([CH3:60])=[N:20][N:19]=3)[C:13]=2[CH:12]=[C:11]1[C:35]1[N:36]=[CH:37][N:38]([CH2:40][CH3:47])[CH:39]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 118159532HCID 118159532, compound

Product 1

HCID 118159856HCID 118159856, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (3.1 mg, 0.078 mmol, 60% in mineral oil) was added to a solution of 6-benzyl-7-(1H-imidazol-4-yl)-1-methyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (5.1 mg, 0.016 mmol, from Example 74) in DMF (0.20 mL). After 10 minutes, iodoethane (3.7 μL, 0.046 mmol, Aldrich) was introduced and the reaction was allowed to proceed for 15 minutes, at which time it was quenched with water. Purification via preparative HPLC-MS (C18 eluting with a gradient of MeCN and H2O containing 0.15% NH4OH) afforded product (3.4 mg, 61%).

Workup

  1. waitto proceed for 15 minutes, at which time it
  2. customwas quenched with water
  3. customPurification via preparative HPLC-MS (C18
  4. washeluting with a gradient of MeCN and H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-5ebc35988761498b92bb648ae935a4e5
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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