Acetic Acid → 1-(4-(((3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methyl)amino)phenyl)butan-1-one

HRID 593299

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.[CH3:13][C:14]1[C:18]([CH:19]=O)=[C:17]([CH3:21])[N:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:15]=1.C(O)(=O)C>C(Cl)Cl.CO.CC(N(C)C)=O>[CH3:13][C:14]1[C:18]([CH2:19][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)=[C:17]([CH3:21])[N:16]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:15]=1

Participants

Conditions

Temperature: 55 °C

Procedure

In a 20 ml vial, to a solution of solution of 1-(4-aminophenyl)butan-1-one (46 mg, 0.28 mmol) dissolved in DCM/MeOH (0.6 mL) was added a solution of 3,5-dimethyl-1-phenyl-1H-pyrazole-4-carbaldehyde (112 mg, 0.56 mmol) in DMA (1.8 mL). A solution of acetic acid (50 mg, 0.84 mmol) in DCM/MeOH (0.6 mL) was then added, followed by the addition of 361 mg of MP-CNBH3 resin (3 eq.; subst. 2.34 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 resulting residue was dissolved in 1:1 DMSO/MeOH. Purification by reverse phase HPLC (TFA method) gave the title compound.

Workup

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

Sources & evidence

ORD record: ord-753f62ebc22d4739aff3da88b7d0bec7
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242933B2

Linked notes

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