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

HRID 593298

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HRID 593298 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 31374Dimethylacetamide용매HCID 21226129Dichloromethane methanol용매2회

반응 조건

온도
55 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e90a9289aeec45d7859d29bd7bf3c7e6
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242933B2

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