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

HRID 593298

反応式

HRID 593298 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.[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

参加物

6

反応物 3

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

生成物 1

HCID 251271501-{4-[(Thiophen-3-ylmethyl)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 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.

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 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-e90a9289aeec45d7859d29bd7bf3c7e6
出典データセット
uspto-grants-2016_01
特許番号
US09242933B2

関連ノート

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