HCID 57837464, compound → HCID 57837482, compound

HRID 731753Notes

Reaction equation

HRID 731753 reaction equation
C([NH:8][CH2:9][CH:10]([CH3:25])[C:11]([C:13]1[C:14]([CH:22]([CH3:24])[CH3:23])=[N:15][N:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=12)=[O:12])C1C=CC=CC=1>CO>[NH2:8][CH2:9][CH:10]([CH3:25])[C:11]([C:13]1[C:14]([CH:22]([CH3:24])[CH3:23])=[N:15][N:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=12)=[O:12]

Participants

3

Reactant 1

HCID 57837464HCID 57837464, compound

Product 1

HCID 57837482HCID 57837482, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(benzylamino)-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one (0.312 g, 0.93 mmol) was dissolved in MeOH (25 mL). The flask was evacuated and flushed with argon (3 cycles). Pd on C (0.312 g, 10 wt %) was added in small portions. The flask was then evacuated and flushed with hydrogen (4 cycles). The heterogeneous mixture was then vigorously stirred for 2 hours before evacuating and flushing with argon (3 cycles). The mixture was then filtered through Celite, washing with MeOH (50 mL), and concentrated. The dark yellow oil was then subjected to flash column chromatography (100% MeOH) while monitoring the fractions with HPLC and 1H NMR. The first major fractions contained 0.164 g (53% recovered starting material); which was followed by 0.0379 g (16% yield) of 3-amino-1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one as a yellow oil.

Workup

  1. customThe flask was evacuated
  2. customflushed with argon (3 cycles)
  3. additionPd on C (0.312 g, 10 wt %) was added in small portions
  4. customThe flask was then evacuated
  5. customflushed with hydrogen (4 cycles)
  6. custombefore evacuating
  7. customflushing with argon (3 cycles)
  8. filtrationThe mixture was then filtered through Celite
  9. washwashing with MeOH (50 mL)
  10. concentrationconcentrated
  11. custom0.164 g (53% recovered starting material)

Sources & evidence

ORD record
ord-32953f71f05e4afab928d3bae94e9acb
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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