Triethylamine → HCID 60142300, compound

HRID 1475938Notes

Reaction equation

HRID 1475938 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:31](/[CH:32]=[CH:33]/[CH2:34][N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)=[C:13]3[CH:14]=[C:15]([C:18]([N:20]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[O:19])[CH:16]=[CH:17][N:12]3[N:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(N(CC)CC)C>CO.[Pd]>[OH:3][CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:31]([CH2:32][CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)=[C:13]3[CH:14]=[C:15]([C:18]([N:20]([CH2:26][CH2:27][CH:28]([CH3:29])[CH3:30])[CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[O:19])[CH:16]=[CH:17][N:12]3[N:11]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 60142164HCID 60142164, compound

Product 1

HCID 60142300HCID 60142300, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(E)-2-(4-acetylphenyl)-N,N-diisopentyl-3-(3-(piperidin-1-yl)prop-1-en-1-yl)pyrazolo[1,5-a]pyridine-5-carboxamide (80 mg, 0.15 mmol) was dissolved in MeOH (3 mL) and triethylamine (1 mL) and 10% Pd/C (40 mg) was added. The vessel was flushed with 3 cycles of vacuum then hydrogen from a balloon, and the reaction mixture was stirred for 4 h at room temperature, filtered through Celite and evaporated. The residue was purified by preparative HPLC on a reverse-phase Zorbax SB-C18 column 21.2×100 mm eluted with MeOH-water-0.1% TFA. Isocratic 30% for 3 minutes then Gradient 30% to 100% MeOH over 14 minutes. LCMS m/z 547.4 (weak) (M+H)+, 458.3 (strong). ret. time=2.35 min.

Workup

  1. customThe vessel was flushed with 3 cycles of vacuum
  2. filtrationfiltered through Celite
  3. customevaporated
  4. customThe residue was purified by preparative HPLC on a reverse-phase Zorbax
  5. washcolumn 21.2×100 mm eluted with MeOH-water-0.1% TFA
  6. waitIsocratic 30% for 3 minutes
  7. waitGradient 30% to 100% MeOH over 14 minutes

Sources & evidence

ORD record
ord-c5d4e2b03a0d47618e538d695d0b3031
Source dataset
uspto-grants-2015_04
Patent number
US09018395B2

Reaction notes

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