Dimethylformamide → US9777003, Example 64

HRID 628310Notes

Reaction equation

HRID 628310 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:17]([CH3:20])=[N:18][N:19]=3)[C:11]=2[CH:10]=[C:9]1[C:21]1[CH:22]=[N:23][NH:24][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.[H-].[Na+].Cl[CH2:34][C:35]#[N:36]>>[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:17]([CH3:20])=[N:18][N:19]=3)[C:11]=2[CH:10]=[C:9]1[C:21]1[CH:22]=[N:23][N:24]([CH2:34][C:35]#[N:36])[CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 136963112US9777003, Example 63

Product 1

HCID 118159501US9777003, Example 64

Procedure

A solution of 6-benzyl-1-methyl-7-(1H-pyrazol-4-yl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (14 mg, 0.043 mmol, from Example 63) in DMF (0.56 mL, 7.2 mmol) was treated with NaH (5.1 mg, 0.21 mmol). After 10 minutes, the mixture was treated with chloroacetonitrile (8.1 μL, 0.13 mmol, Fluka). After 10 minutes, the reaction was quenched by the addition of water. The product was purified via preparative HPLC-MS (C18 eluting with a gradient of MeCN and H2O containing 0.15% NH4OH). Yield: (7.0 mg, 45%).

Workup

  1. waitAfter 10 minutes
  2. customthe reaction was quenched by the addition of 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-d872a90a200e4bc08111201ceb5666ae
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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