Acetic Acid → 1-{4-[(Thiophen-3-ylmethyl)amino]phenyl}-butan-1-one

HRID 593298

Reaction equation

HRID 593298 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:12])[CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.[S:13]1[CH:17]=[CH:16][C:15]([CH:18]=O)=[CH:14]1.C(O)(=O)C>C(Cl)Cl.CO.CC(N(C)C)=O>[S:13]1[CH:17]=[CH:16][C:15]([CH2:18][NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8](=[O:12])[CH2:9][CH2:10][CH3:11])=[CH:6][CH:7]=2)=[CH:14]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 155271-Butanone, 1-(4-aminophenyl)-HCID 681353-Thiophenecarboxaldehyde

Product 1

HCID 251271501-{4-[(Thiophen-3-ylmethyl)amino]phenyl}-butan-1-one

Reagents, catalysts & solvents 2

HCID 31374DimethylacetamideSolventHCID 21226129Dichloromethane methanolSolvent2×

Conditions

Temperature
55 °C

Procedure

In a 20 mL vial, to a solution of 1-(4-aminophenyl)-butan-1-one (19.64 mg, 0.1 mmol) in DCM/MeOH (0.7 mL) was added a solution of thiophene-3-carbaldehyde (22.4 mg, 0.2 mmol) in DMA (0.8 mL). A solution of acetic acid (18 mg, 0.3 mmol) in DCM/MeOH (0.7 mL) was added, followed by the addition of 160 mg of MP-CNBH3 resin (3 eq.; subst. 2.25 mmoles/g). The vial was capped and was then heated with shaking overnight at 55° C. The progress of the reaction was monitored by LC/MS. After completion of the reaction, the reaction mixture was concentrated to dryness. The residue was dissolved in 1:1 DMSO/MeOH. Purification by reverse phase HPLC (TFA method) gave the title compound.

Workup

  1. customThe vial was capped
  2. temperaturewas then heated
  3. customAfter completion of the reaction
  4. concentrationthe reaction mixture was concentrated to dryness
  5. dissolutionThe residue was dissolved in 1:1 DMSO/MeOH
  6. customPurification by reverse phase HPLC (TFA method)

Sources & evidence

ORD record
ord-e90a9289aeec45d7859d29bd7bf3c7e6
Source dataset
uspto-grants-2016_01
Patent number
US09242933B2

Linked notes

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