5-(hydrazinecarbonyl)-N-(pyridine-4-ylmethyl)thiophene-2-carboxamide → HCID 86669400, compound

HRID 337383Notes

Reaction equation

HRID 337383 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:14]([CH3:15])[N:13]=[C:12]([C:16](=O)[CH3:17])[C:11]=3[OH:19])=[CH:7][CH:8]=2)[CH2:3][CH2:2]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][N:36]=[CH:35][CH:34]=2)=[O:30])=[CH:26][CH:25]=1)=[O:23])[NH2:21]>CS(C)=O>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[N:14]([CH3:15])[N:13]=[C:12]([C:16](=[N:21][NH:20][C:22]([C:24]4[S:28][C:27]([C:29]([NH:31][CH2:32][C:33]5[CH:34]=[CH:35][N:36]=[CH:37][CH:38]=5)=[O:30])=[CH:26][CH:25]=4)=[O:23])[CH3:17])[C:11]=3[OH:19])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 576881445-(hydrazinecarbonyl)-N-(pyridine-4-ylmethyl)thiophene-2-carboxamideHCID 68161693HCID 68161693, compound

Product 1

HCID 86669400HCID 86669400, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-[5-(2,3-Dihydro-1H-inden-5-yl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethanone (30 mg, 0.117 mmol) and 5-(hydrazinecarbonyl)-N-(pyridine-4-ylmethyl)thiophene-2-carboxamide (32 mg, 0.117 mmol, synthesized in accordance with WO2007010954) in dimethyl sulfoxide (0.9 mL) was heated at 100° C. for 3 days with stirring. After the reaction, the reaction solution was concentrated under reduced pressure. After addition of chloroform and ethyl acetate, the resulting crystals were collected by filtration and dried under reduced pressure to obtain the desired product (44 mg, 73% yield).

Workup

  1. customAfter the reaction
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additionAfter addition of chloroform and ethyl acetate
  4. filtrationthe resulting crystals were collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-6181af75428047a0af1225261683c0db
Source dataset
uspto-grants-2014_11
Patent number
US08889732B2

Reaction notes

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