HCID 86691861, compound → HCID 86691862, compound

HRID 1616250Notes

Reaction equation

HRID 1616250 reaction equation
[CH3:1][C:2]([CH3:26])([CH3:25])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C:13]3[CH:14]=[C:15]([CH2:20][C:21]#[N:22])[CH:16]=[CH:17][C:18]=3[CH3:19])=[CH:10][CH:11]=2)[N:6]([CH3:23])[C:5]1=[O:24]>N.CCO.[Ni]>[NH2:22][CH2:21][CH2:20][C:15]1[CH:16]=[CH:17][C:18]([CH3:19])=[C:13]([C:9]2[N:8]=[C:7]3[N:6]([CH3:23])[C:5](=[O:24])[N:4]([CH2:3][C:2]([CH3:1])([CH3:25])[CH3:26])[C:12]3=[CH:11][CH:10]=2)[CH:14]=1

Participants

5

Reactant 1

HCID 86691861HCID 86691861, compound

Product 1

HCID 86691862HCID 86691862, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

Raney 2800 Nickel (30 mg, suspended in water) was added to a 25 mL receiver flask. The black solid was rinsed with EtOH and a solution of 82-2 (38 mg, 0.11 mmol) dissolved in 2M ammonia in EtOH (2 mL) was added. The flask was purged with hydrogen and the reaction was stirred at room temperature under a balloon of hydrogen. After 3 hours, the flask was purged with nitrogen and the mixture was filtered, rinsed with EtOH and concentrated. Purified by reverse phase (Sunfire C18, 25-85% CH3CN/0.1% TFA in water) and the fractions containing product were passed through an SCX cation exchange column, washed with acetonitrile, and eluted with 2M ammonia in EtOH to give 82-3 as a colorless oil. HRMS (M+H)+: observed=353.2, calculated=353.5.

Workup

  1. washThe black solid was rinsed with EtOH
  2. additionwas added
  3. customThe flask was purged with hydrogen
  4. customthe flask was purged with nitrogen
  5. filtrationthe mixture was filtered
  6. washrinsed with EtOH
  7. concentrationconcentrated
  8. customPurified by reverse phase (Sunfire C18, 25-85% CH3CN/0.1% TFA in water)
  9. additionthe fractions containing product
  10. washwashed with acetonitrile
  11. washeluted with 2M ammonia in EtOH

Sources & evidence

ORD record
ord-15ed7b4c6b8a457ca4d84cdeb445c128
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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