Acetic Acid → HCID 69588712, compound

HRID 859142Notes

Reaction equation

HRID 859142 reaction equation
[CH3:1][C:2]1[C:10]([NH2:11])=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:12][CH2:13][C:14](=O)[CH2:15][CH3:16].[BH3-]C#N.[Na+].C(O)(=O)C>CO>[CH2:13]([CH:14]([NH:11][C:10]1[C:2]([CH3:1])=[N:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12)[CH2:15][CH3:16])[CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7288Ethyl ketoneHCID 5003444Sodium cyanoborohydrideHCID 19380186HCID 19380186, compound

Product 1

HCID 69588712HCID 69588712, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-methyl-3-amino-pyrazolo[1,5-a]pyridine (0.158 g, 1.07 mmol) and 3-pentanone (0.11 g, 0.14 mL, 1.29 mmol) in methanol (5.0 mL) was added NaCNBH3 (0.095 g, 1.5 mmol) and a drop of acetic acid. The mixture was stirred at room temperature for 18 h. The reaction was partitioned between CH2Cl2 and H2O. The layers were separated and the aqueous layer was extracted with CH2Cl2 (2×). The organic layers were combined and dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to column chromatography (15% ethyl acetate/hexane) to give 0.196 g (85%) of a yellow oil as the title compound: 1H NMR (400 MHz, CDCl3) δ 8.25 (d, J=7.0 Hz, 1H), 7.37 (d, J=8.9 Hz, 1H), 6.99–6.95 (m, 1H), 6.59 (t, J=6.8 Hz, 1H), 2.87 (quintet, J=5.9 Hz, 1H), 2.44 (s, 3H), 1.57–1.47 (m, 4H), 1.01 (t, J=7.4 Hz, 6H); HRMS (FAB) calcd for C13H19N3+H 218.1657. found 218.1647.

Workup

  1. customThe reaction was partitioned between CH2Cl2 and H2O
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (2×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-09001c2b1acb49f79e1d404981fa3dd2
Source dataset
uspto-grants-2006_12
Patent number
US07151109B2

Reaction notes

Loading…