HCID 86649103, compound → A-1242846

HRID 1470937Notes

Reaction equation

HRID 1470937 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C@H:15]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[CH2:14][CH2:13][C@H:12]2[C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CCCCCCC>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C@H:15]([C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=3)[CH2:14][CH2:13][C@H:12]2[C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 86649103HCID 86649103, compound

Product 1

HCID 67239053A-1242846

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

To a 160 ml Parr stirrer hydrogenation vessel was added the product from Example 37D (2 g, 4.49 mmol), followed by 60 ml of THF, and Raney Nickel Grace 2800 (1 g, 50 wt % (dry basis)) under a stream of nitrogen. The reactor was assembled and purged with nitrogen (8×20 psig) followed by purging with hydrogen (8×30 psig). The reactor was then pressurized to 30 psig with hydrogen and agitation (700 rpm) began and continued for a total of 16 h at room temperature. The slurry was filtered by vacuum filtration using a GF/F Whatman glass fiber filter. Evaporation of the filtrate to afford a slurry followed by the addition heptane and filtration gave the crude title compound, which was dried and used directly in the next step.

Workup

  1. dry with materialfollowed by 60 ml of THF, and Raney Nickel Grace 2800 (1 g, 50 wt % (dry basis)) under a stream of nitrogen
  2. custompurged with nitrogen (8×20 psig)
  3. customby purging with hydrogen (8×30 psig)
  4. customcontinued for a total of 16 h at room temperature
  5. filtrationThe slurry was filtered by vacuum filtration
  6. filtrationfilter
  7. customEvaporation of the filtrate
  8. customto afford a slurry

Sources & evidence

ORD record
ord-12f33ba0558a45d399e890783ed56d65
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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