Pyridine → HCID 178491584, 화합물

HRID 1911300노트

반응식

HRID 1911300 반응식
ClC(N(C)C)=C(C)C.[CH3:9][O:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1.[NH2:20][C:21]1[N:25](C(OC(C)(C)C)=O)[N:24]=[C:23]([CH2:33][CH2:34][C:35]2[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[C:37]([O:43][CH3:44])[CH:36]=2)[CH:22]=1.N1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:42][O:41][C:39]1[CH:40]=[C:35]([CH2:34][CH2:33][C:23]2[CH:22]=[C:21]([NH:20][C:15](=[O:17])[C:14]3[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:19][CH:18]=3)[NH:25][N:24]=2)[CH:36]=[C:37]([O:43][CH3:44])[CH:38]=1

참가 물질

7

반응물 5

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 74784-Methoxybenzoic AcidHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 57440371Tert-butyl 5-amino-3-[2-(3,5-dimethoxyphenyl)ethyl]pyrazole-1-carboxylate

생성물 1

HCID 178491584HCID 178491584, 화합물수율 52%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

1-Chloro-N,N,2-trimethylprop-1-en-1-amine (89 μl, 0.63 mmol, 1.05 eq) was added dropwise to 4-methoxybenzoic acid (97 mg, 0.63 mmol, 1 eq) in DCM (1.5 ml) at ambient temperature. After stirring at ambient temperature for 1.5 h, a solution of tert-butyl 5-amino-3-[2-(3,5-dimethoxyphenyl)ethyl]pyrazole-1-carboxylate (199 mg, 0.57 mmol, 0.9 eq) and pyridine (142 μL, 1.74 mmol, 2.75 eq) in DCM (2 ml) was added to the reaction mixture and stirring was continued at ambient temperature for a further 3 h. A solution of TFA (386 μL, 5.2 mmol, 8.25 eq) in DCM (3.5 ml) was then added and stirring was continued at ambient temperature for 18 h. The reaction mixture was concentrated and the crude product was purified by reverse-phase prep. HPLC (basic) using a 33-53% gradient of acetonitrile in water containing 1% ammonium hydroxide solution. The clean fractions were taken and evaporated to afford the title compound as a colourless foamy solid (113 mg, 52% yield).

후처리

  1. stirringstirring
  2. waitwas continued at ambient temperature for a further 3 h
  3. stirringstirring
  4. waitwas continued at ambient temperature for 18 h
  5. concentrationThe reaction mixture was concentrated
  6. customthe crude product was purified by reverse-phase prep
  7. customevaporated

출처 및 근거

ORD 기록
ord-d4711669a2a64ad385801e9ba6075519
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604022B2

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