Water → HCID 72682952, compound

HRID 1094931Notes

Reaction equation

HRID 1094931 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[S:10][CH:11]=[C:12]([C:15]([CH3:17])=O)[C:13]=2[OH:14])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:18]([C:20]([C:22]1[S:26][C:25]([C:27]([NH:29][CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:28])=[CH:24][CH:23]=1)=[O:21])[NH2:19].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[S:10][CH:11]=[C:12]([C:15](=[N:19][NH:18][C:20]([C:22]3[S:26][C:25]([C:27]([NH:29][CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:28])=[CH:24][CH:23]=3)=[O:21])[CH3:17])[C:13]=2[OH:14])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 442072882-(3,4-Dichlorophenyl)-3-hydroxy-4-(methylcarbonyl)thiopheneHCID 60206773HCID 60206773, compound

Product 1

HCID 72682952HCID 72682952, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-(3,4-Dichlorophenyl)-3-hydroxy-4-methylcarbonylthiophene (24 mg, 0.083 mmol) in isopropanol (2.0 mL) was heated with tert-butyl 3-{[5-(hydrazinocarbonyl)thiophene-2-carbonyl]amino}propionate (18 mg, 0.057 mmol) prepared in Reference Synthetic Example 7 and 6 mg of p-toluenesulfonic acid monohydrate at 100° C. for 8 hours and allowed to cool to room temperature. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed with water, methanol and chloroform and dried to give 28 mg of the desired product (yield 85%).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with water, methanol and chloroform
  3. customdried

Sources & evidence

ORD record
ord-f0e3ee56981a41379fb19517d469b758
Source dataset
uspto-grants-2012_03
Patent number
US08134013B2

Reaction notes

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