5-(hydrazinecarbonyl)-N-[4-(2-hydroxyethylcarbamoyl)benzyl]thiophene-2-carboxamide → 5-(2-{1-[4-Hydroxy-5-(5,6,7,8-tetrahydronaphthalen-2-yl)thiophen-3-yl]ethylidene}hydrazinecarbonyl)-N-[4-(2-hydroxyethylcarbamoyl)benzyl]thiophene-2-carboxamide

HRID 337387Notes

Reaction equation

HRID 337387 reaction equation
[OH:1][C:2]1[C:3]([C:17](=O)[CH3:18])=[CH:4][S:5][C:6]=1[C:7]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1.[NH:20]([C:22]([C:24]1[S:28][C:27]([C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39](=[O:44])[NH:40][CH2:41][CH2:42][OH:43])=[CH:35][CH:34]=2)=[O:30])=[CH:26][CH:25]=1)=[O:23])[NH2:21]>>[OH:1][C:2]1[C:3]([C:17](=[N:21][NH:20][C:22]([C:24]2[S:28][C:27]([C:29]([NH:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([C:39](=[O:44])[NH:40][CH2:41][CH2:42][OH:43])=[CH:35][CH:34]=3)=[O:30])=[CH:26][CH:25]=2)=[O:23])[CH3:18])=[CH:4][S:5][C:6]=1[C:7]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1

Participants

3

Reactant 2

HCID 676353705-(hydrazinecarbonyl)-N-[4-(2-hydroxyethylcarbamoyl)benzyl]thiophene-2-carboxamideHCID 681616421-[4-Hydroxy-5-(5,6,7,8-tetrahydronaphthalen-2-yl)thiophen-3-yl]ethanone

Product 1

HCID 759653875-(2-{1-[4-Hydroxy-5-(5,6,7,8-tetrahydronaphthalen-2-yl)thiophen-3-yl]ethylidene}hydrazinecarbonyl)-N-[4-(2-hydroxyethylcarbamoyl)benzyl]thiophene-2-carboxamideYield 65%

Procedure

Synthesis was carried out in the same manner as in Synthetic Example 1 by using 24.4 mg (0.0895 mmol) of 1-[4-hydroxy-5-(5,6,7,8-tetrahydronaphthalen-2-yl)thiophen-3-yl]ethanone and 32.6 mg (0.0900 mmol) of 5-(hydrazinecarbonyl)-N-[4-(2-hydroxyethylcarbamoyl)benzyl]thiophene-2-carboxamide to obtain the desired product (35.8 mg, yield 65%).

Workup

  1. customSynthesis

Sources & evidence

ORD record
ord-dfb60bf8396e465f9de77672c0c9355e
Source dataset
uspto-grants-2014_11
Patent number
US08889732B2

Reaction notes

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