Isoniazid → N-(5-(4-(4-Cyanophenyl)piperidine-1-carbonyl)-2-methylphenyl)-2-isonicotinoylhydrazinecarboxamide

HRID 541410Notes

Reaction equation

HRID 541410 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:5]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=[O:6].C(N(CC)CC)C.[C:32](Cl)(Cl)=[O:33].[C:36]([NH:44][NH2:45])(=[O:43])[C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1>C(Cl)Cl>[C:17]([C:16]1[CH:15]=[CH:14][C:13]([CH:10]2[CH2:9][CH2:8][N:7]([C:5]([C:4]3[CH:21]=[CH:22][C:23]([CH3:24])=[C:2]([NH:1][C:32]([NH:45][NH:44][C:36](=[O:43])[C:37]4[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=4)=[O:33])[CH:3]=3)=[O:6])[CH2:12][CH2:11]2)=[CH:20][CH:19]=1)#[N:18]

Participants

6

Reactant 4

HCID 3767IsoniazidHCID 6371PhosgeneHCID 8471TriethylamineHCID 576669154-(1-(3-Amino-4-methylbenzoyl)piperidin-4-yl)benzonitrile2×

Product 1

HCID 68288800N-(5-(4-(4-Cyanophenyl)piperidine-1-carbonyl)-2-methylphenyl)-2-isonicotinoylhydrazinecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-(1-(3-Amino-4-methylbenzoyl)piperidin-4-yl)benzonitrile (compound 121.1, 0.1 g, 0.31 mmol) and triethyl amine (0.09 ml, 0.62 mmol) in DCM (5 ml) was added to a solution of phosgene (20% in toluene, 0.31 ml, 0.62 mmol) in DCM (5 ml) at 0° C. After the resulting reaction mixture was stirred at room temperature for 1.5 hours, all solvents were removed under reduced pressure. The residue was dried under high-vacuum for 30 minutes then was re-dissolved in EtOH (5 ml). Isonicotinohydrazide (0.05 g, 0.34 mmol) was added. The mixture was heated at 80° C. over night. The ethanol was removed and the residue was purified using prep.-TLC (10% MeOH in DCM) to give the product as a light brown solid. Yield: 0.14 g, 93%. m/z (ES+) 483.2 (M+H)+.

Workup

  1. customAfter the resulting reaction mixture
  2. customall solvents were removed under reduced pressure
  3. customThe residue was dried under high-vacuum for 30 minutes
  4. dissolutionthen was re-dissolved in EtOH (5 ml)
  5. temperatureThe mixture was heated at 80° C. over night
  6. customThe ethanol was removed
  7. customthe residue was purified

Sources & evidence

ORD record
ord-e7134e189a0e40148226645e3d6d3836
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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