Acetohydrazide → Acetic acid N'-(2-{4,5-dimethyl-6-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridazin-3-yl}-acetyl)-hydrazide

HRID 447134Notes

Reaction equation

HRID 447134 reaction equation
[C:1]([NH:4][NH2:5])(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:15][C:16]1[C:21]([CH3:22])=[C:20]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][N:30]=3)[CH2:25][CH2:24]2)[N:19]=[N:18][C:17]=1[CH2:39][C:40](O)=[O:41].C1C=CC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:15][C:16]1[C:21]([CH3:22])=[C:20]([N:23]2[CH2:28][CH2:27][N:26]([C:29]3[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][N:30]=3)[CH2:25][CH2:24]2)[N:19]=[N:18][C:17]=1[CH2:39][C:40]([NH:5][NH:4][C:1](=[O:3])[CH3:2])=[O:41]

Participants

7

Reactant 5

HCID 14039AcetohydrazideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59191538{4,5-Dimethyl-6-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridazin-3-yl}-acetic acid

Product 1

HCID 59191525Acetic acid N'-(2-{4,5-dimethyl-6-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridazin-3-yl}-acetyl)-hydrazideYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acetic acid hydrazide (20.6 mg, 0.28 mmol) is added to a round-bottom flask under N2 followed by DMF (5 mL). Diisopropylethylamine (0.25 mL) is added and the reaction is stirred for 30 min. {4,5-Dimethyl-6-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazin-1-yl]-pyridazin-3-yl}-acetic acid (110 mg, 0.28 mmol) is added and the reaction is stirred for 1 h. HOBT (42 mg, 0.311 mmol) and HBTU (116.8 mg, 0.31 mmol) are added and the reaction is allowed to stir for 16 h. The crude reaction mixture is purified via flash chromatography on silica gel (0-30% methanol in dichloromethane) to afford the title compound (114 mg, 90%).

Workup

  1. additionis added
  2. stirringto stir for 16 h
  3. customThe crude reaction mixture
  4. customis purified via flash chromatography on silica gel (0-30% methanol in dichloromethane)

Sources & evidence

ORD record
ord-6dc2d91fa5234e7ab92763689813ca42
Source dataset
uspto-grants-2013_07
Patent number
US08481542B2

Reaction notes

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