Sodium hydride → US9777003, Example 24

HRID 628265Notes

Reaction equation

HRID 628265 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:8]2[C:9]3[CH:15]=[C:14]([CH3:16])[NH:13][C:10]=3[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1.Br[CH:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:19][CH2:20][CH2:21][CH3:22]>CN(C=O)C>[CH3:3][C:4]1[N:8]2[C:9]3[CH:15]=[C:14]([CH3:16])[N:13]([CH:18]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:19][CH2:20][CH2:21][CH3:22])[C:10]=3[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10900349(1-Bromopentyl)benzeneHCID 1369631111,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 118159523US9777003, Example 24

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.011 g, 0.27 mmol, 60% in mineral oil) was added to a solution of 1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (50.0 mg, 0.268 mmol, from Example 2, Step 5) in DMF (6 mL). After stirring for 10 minutes, (1-bromopentyl)benzene (0.061 g, 0.27 mmol, from Step 1) was added. After stirring for 45 minutes, the reaction was quenched by the addition of water and the mixture was diluted with MeCN, filtered and purified via preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (0.01 g, 10%).

Workup

  1. stirringAfter stirring for 45 minutes
  2. customthe reaction was quenched by the addition of water
  3. additionthe mixture was diluted with MeCN
  4. filtrationfiltered
  5. custompurified via preparative HPLC-MS (Waters XBridge C18
  6. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH) (0.01 g, 10%)

Sources & evidence

ORD record
ord-d5663a6d55b741bd9316bd34c98067b8
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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