Diisopropylethylamine → 2-(4-Chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylic acid N'-(4-methoxybenzyl)-N'-methyl hydrazide

HRID 1498922Notes

Reaction equation

HRID 1498922 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:14]([OH:16])=O)=[C:11]([CH3:13])[N:12]=2)=[C:4]([O:17][CH3:18])[CH:3]=1.[CH3:19][O:20][C:21]1[CH:30]=[CH:29][C:24]([CH2:25][N:26]([CH3:28])[NH2:27])=[CH:23][CH:22]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C.C1(C)C=CC=CC=1.CN(C)C=O>[CH3:19][O:20][C:21]1[CH:30]=[CH:29][C:24]([CH2:25][N:26]([CH3:28])[NH:27][C:14]([C:10]2[S:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=3[O:17][CH3:18])=[N:12][C:11]=2[CH3:13])=[O:16])=[CH:23][CH:22]=1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68017764N-(4-Methoxybenzyl)-N-methylhydrazineHCID 686420482-(4-Chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 686424892-(4-Chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylic acid N'-(4-methoxybenzyl)-N'-methyl hydrazideYield 67.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584019Toluene ethylacetateSolvent

Procedure

To N,N-dimethylformamide (12 ml), 2-(4-chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylic acid (1.02 g) prepared in Example 7-1, N-(4-methoxybenzyl)-N-methylhydrazine (718 mg) prepared in Example 14-1, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (828 mg), 1-hydroxy-1H-benzotriazole monohydrate (662 mg) and N,N-diisopropylethylamine (558 mg), and the mixture was stirred at a room temperature for 22 hours. An ethyl acetate-toluene (3:1) solution was added thereto. The resulting mixture was washed with water, a 5% potassium bisulfate aqueous solution, a saturated sodium bicarbonate solution and a saturated saline solution in order, and then dried over sodium sulfate and concentrated under a reduced pressure. The concentrate was purified by silica gel column chromatography (chloroform:methanol=100:1) to give the title compound (1.05 g, 67%).

Workup

  1. washThe resulting mixture was washed with water
  2. dry with materiala 5% potassium bisulfate aqueous solution, a saturated sodium bicarbonate solution and a saturated saline solution in order, and then dried over sodium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customThe concentrate was purified by silica gel column chromatography (chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-8784572d90ab4de899f78d5bdaace309
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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