Nicotinic acid, hydrazide → HCID 15434926, compound

HRID 612405Notes

Reaction equation

HRID 612405 reaction equation
[CH:1]1([N:6]2[C:10]3[C:11](SC)=[N:12][CH2:13][CH2:14][C:9]=3[C:8]([CH2:17][CH3:18])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19]([NH:27][NH2:28])(=O)[C:20]1[CH:25]=[CH:24][CH:23]=[N:22][CH:21]=1>N1C=CC=CC=1>[CH:1]1([N:6]2[C:10]3[C:11]4[N:12]([C:19]([C:20]5[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=5)=[N:27][N:28]=4)[CH2:13][CH2:14][C:9]=3[C:8]([CH2:17][CH3:18])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 11112Nicotinic acid, hydrazideHCID 15434925HCID 15434925, compound

Product 1

HCID 15434926HCID 15434926, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
135 °C

Procedure

1-Cyclopentyl-4,5-dihydro-3-ethyl-7-methylthio-1H-pyrazolo[3,4-c]pyridine (0.036 grams, 0.14 mmoles) and nicotinic acid hydrazide (0.021 grams, 0.15 mmoles) was dissolved in anhydrous pyridine (5 ml) in a flame dried flask. An oven-dried condenser was added, which was septa sealed and had an outlet to a bubbler. A long stainless steel needle was pierced through the septa and condenser center into the magnetically stirred solution. Nitrogen was bubbled through the long needle. The flask was heated to 135° C. for 4 hours. The pyridine was then removed under nitrogen purge. The resulting oil was heated to 150° C. for 4 hours. The flask was cooled to ambient temperature and contained 0.045 grams of the crude title compound as a white solid. The crude product did not contain any impurities measurable by thin layer chromatography. The product can be purified by either column chromatography on a silica gel column using a gradient mixture of ethyl acetate/hexane as eluent or by recrystallization from a mixture of ethyl acetate in hexane. Melting Point 140-5° C. (crude); 1H NMR (300 MHz, CDCl3) δ 1.24 (t, J=7.6 Hz, 3H), 1.72 (m, 2H), 1.94 (m, 2H) 2.16 (m, 4H), 2.66 (q, J=7.6 Hz, 2H), 2.98 (t, J=7.0 Hz, 2H), 4.25 (t, J=7.0 Hz, 2H), 5.60 (quintet, J=7.7 Hz, 1H), 7.48 (dd, J=4.9 and 7.8 Hz, 1H), 8.05 (d, J=8.0 Hz, 1H), 8.75 (dd, J=1.4 and 4.9 Hz, 1H), 8.9 (d, J=1.7 Hz, 1H); Anal. calcd. for C19H22N6 : C, 68.23; H, 6.63; N, 25.13. Found: C, 67.39; H, 6.87; N, 24.00.

Workup

  1. customdried flask
  2. additionAn oven-dried condenser was added
  3. customwhich was septa sealed
  4. customNitrogen was bubbled through the long needle
  5. customThe pyridine was then removed under nitrogen
  6. custompurge
  7. temperatureThe resulting oil was heated to 150° C. for 4 hours
  8. temperatureThe flask was cooled to ambient temperature
  9. customThe product can be purified by either column chromatography on a silica gel column
  10. additiona gradient mixture of ethyl acetate/hexane as eluent
  11. customby recrystallization
  12. additionfrom a mixture of ethyl acetate in hexane

Sources & evidence

ORD record
ord-f5b63f01ecce4bb8a4ed3c124a0eecc0
Source dataset
uspto-grants-1999_12
Patent number
US06004974

Reaction notes

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