Dimethylformamide → US9777003, Example 7

HRID 628255Notes

Reaction equation

HRID 628255 reaction equation
C([O-])([O-])=O.[K+].[K+].Br.Br[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[CH3:16][C:17]1[N:21]2[C:22]3[CH:28]=[C:27]([CH3:29])[NH:26][C:23]=3[CH:24]=[CH:25][C:20]2=[N:19][N:18]=1.CN(C=O)C>CC#N>[CH3:16][C:17]1[N:21]2[C:22]3[CH:28]=[C:27]([CH3:29])[N:26]([CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=4)[C:23]=3[CH:24]=[CH:25][C:20]2=[N:19][N:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 1369631111,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 118159720US9777003, Example 7Yield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

K2CO3 (44 mg, 0.32 mmol) and 2-(bromomethyl)pyridine hydrobromide (0.027 g, 0.11 mmol, Aldrich) were added to a solution of 1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine (20. mg, 0.11 mmol) in DMF (3.0 mL, 39 mmol). After stirring at room temperature for 2 hours, the reaction was heated to 50° C. for 35 minutes. The reaction mixture was diluted with MeCN, filtered and purified by preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) to afford product (8.9 mg, 30%).

Workup

  1. temperaturethe reaction was heated to 50° C. for 35 minutes
  2. filtrationfiltered
  3. custompurified by preparative HPLC-MS (Waters XBridge C18
  4. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)

Sources & evidence

ORD record
ord-fab9f37f367346cf9abc21409c3286b5
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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