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

HRID 593299

反応式

HRID 593299 の反応式
[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

参加物

6

反応物 3

HCID 176Acetic AcidHCID 155271-Butanone, 1-(4-aminophenyl)-HCID 891791H-Pyrazole-4-carboxaldehyde, 3,5-dimethyl-1-phenyl-

生成物 1

HCID 687227151-(4-(((3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methyl)amino)phenyl)butan-1-one

試薬・触媒・溶媒 2

HCID 31374Dimethylacetamide溶媒HCID 21226129Dichloromethane methanol溶媒2 回

反応条件

温度
55 °C

実験手順

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.

後処理

  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 resulting residue was dissolved in 1:1 DMSO/MeOH
  6. customPurification by reverse phase HPLC (TFA method)

出典と根拠

ORDレコード
ord-753f62ebc22d4739aff3da88b7d0bec7
出典データセット
uspto-grants-2016_01
特許番号
US09242933B2

関連ノート

読み込み中…