Hydrazine hydrate (1:1) → HCID 23107289, compound

HRID 1094999Notes

Reaction equation

HRID 1094999 reaction equation
C([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[S:8][C:7]=1[NH:19][C:20](=[O:33])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH:22]=1)=O)C.O.[NH2:35][NH2:36]>C(O)C>[CH2:31]([N:28]([CH2:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[C:20]([NH:19][C:7]1[S:8][C:9]([CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:10]([CH3:11])[C:6]=1[C:4]([NH:35][NH2:36])=[O:3])=[O:33])[CH2:29][CH3:30])[CH3:32]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66638661HCID 66638661, compound

Product 1

HCID 23107289HCID 23107289, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Subsequently, 2-(3-diethylaminomethyl-benzoylamino)-4-methyl-5-piperidin-1-ylmethylthiophene-3-carboxylic acid ethyl ester (79 mg) was dissolved in ethanol (10 ml), hydrazine monohydrate (2 ml) was added dropwise to the solution at room temperature, and a reaction was then allowed to proceed at that temperature for 12 hr. After the completion of the reaction, the reaction system was concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 3-diethylaminomethyl-N-(3-hydrazinocarbonyl-4-methyl-5-piperidin-1-ylmethylthiophen-2-yl)-benzamide as a useful intermediate (30 mg, yield 38%).

Workup

  1. customAfter the completion of the reaction
  2. concentrationthe reaction system was concentrated under the reduced pressure
  3. customThe residue was purified by column chromatography
  4. washeluted with a chloroform-methanol system

Sources & evidence

ORD record
ord-348fe8895b4f49949ecbe465c9b0296e
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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