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

HRID 593299

반응식

HRID 593299 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.[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

참가 물질

6

반응물 3

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

생성물 1

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

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

출처 및 근거

ORD 기록
ord-753f62ebc22d4739aff3da88b7d0bec7
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242933B2

연결된 노트

불러오는 중…