Benzaldehyde → HCID 178480690, compound

HRID 736288Notes

Reaction equation

HRID 736288 reaction equation
[NH:1]([C:3]([C:5]1[S:28][C:8]2[NH:9][N:10]=[C:11]([NH:12][C:13](=[O:27])[C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[C:7]=2[CH:6]=1)=[O:4])[NH2:2].C(O)C.[CH:32](=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl>Cl.O1CCCC1>[CH:32](=[N:2][NH:1][C:3]([C:5]1[S:28][C:8]2[NH:9][N:10]=[C:11]([NH:12][C:13](=[O:27])[C:14]3[CH:15]=[CH:16][C:17]([N:20]4[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]4)=[CH:18][CH:19]=3)[C:7]=2[CH:6]=1)=[O:4])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 702EthanolHCID 178480689HCID 178480689, compound

Product 1

HCID 178480690HCID 178480690, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

N-(5-Hydrazinocarbonyl-1H-thieno[2,3-c]pyrazol-3-yl)-4-(4-methylpiperazin-1-yl)-benzamide (0.150 g, 0.318 mmol, 1 eq.), ethanol (1 mL) and, by syringe, benzaldehyde (0.048 mL, 0.47 mmol, 1.3 eq.) are placed in a dry 5 mL round-bottomed flask under argon. Two drops of 5 N hydrochloric acid are added to the suspension. The reaction mixture is stirred at a temperature in the region of 50° C. for 3 hours, the solvent is then evaporated off and the residue is placed directly on a column of neutralized silica gel. Elution is performed with a methanol/dichloromethane mixture (10/90 by volume). The product obtained is directly added to a mixture of 1 mL of tetrahydrofuran and 0.5 mL of 5 N hydrochloric acid. The precipitate obtained is filtered off, washed with water and dried. N-[5-(Benzylidenehydrazinocarbonyl)-1H-thieno[2,3-c]pyrazol-3-yl]-4-(4-methylpiperazin-1-yl)benzamide is obtained in the form of a white solid (0.029 g, 16%). MS: ES m/z=488 MH+ base peak. 1H NMR (400 MHz, (CD3)2SO-d6, δ in ppm): 2.53 (partially masked s, 3H); 2.87 (m, 4H); 3.47 (m, 4H); 7.03 (d, J=9.0 Hz, 2H); from 7.39 to 7.49 (m, 3H); 7.79 (d, J=7.5 Hz, 2H); 8.01 (d, J=9.0 Hz, 2H); 8.28 (s, 1H); 8.39 (s, 1H).

Workup

  1. customthe solvent is then evaporated off
  2. washElution
  3. customThe product obtained
  4. customThe precipitate obtained
  5. filtrationis filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-c8e9adad88c1450095ceb3b211bf45f7
Source dataset
uspto-grants-2009_09
Patent number
US07595320B2

Reaction notes

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