Diisopropylethylamine → Methyl 4-methoxy-3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoate

HRID 219956노트

반응식

HRID 219956 반응식
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[CH:6][C:5]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:53][C:54](=[N:67]O)[C:55]1[CH:56]=[C:57]([CH:62]=[CH:63][C:64]=1[O:65][CH3:66])[C:58]([O:60][CH3:61])=[O:59]>CN(C=O)C>[CH3:66][O:65][C:64]1[CH:63]=[CH:62][C:57]([C:58]([O:60][CH3:61])=[O:59])=[CH:56][C:55]=1[C:54]1[N:53]=[C:10]([C:8]2[CH:7]=[CH:6][C:5]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])=[C:4]([CH2:3][O:2][CH3:1])[CH:9]=2)[O:12][N:67]=1

참가 물질

6

반응물 4

HCID 81531Diisopropylethylamine2회HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53410613Methyl 3-[amino(hydroxyimino)methyl]-4-methoxybenzoateHCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid

생성물 1

HCID 59495740Methyl 4-methoxy-3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of Intermediate 28 (149.42 mg; 0.58 mmol) and n-ethyldiisopropylamine (198.29 μL; 1.17 mmol) in anhydrous DMF (2 mL) and cooled at 0° C., HATU (221.67 mg; 0.58 mmol) was added and the mixture stirred at RT for 10 min. After this time, Intermediate 53 (100 mg; 0.60 mmol) and DIEA (0.10 mL) in anhydrous DMF (1 mL) were added and the mixture was heated at 80° C. for 18 h. The reaction mixture was cooled to RT, partitioned between water and Et2O, dried over MgSO4, filtered and evaporated under vacuum. Product was adsorbed on silica and purified by flash chromatography (cHex/EtOAc from 9:1 to 8:2), which gave the title compound as a colorless oil. LC/MS (Method B): 445.2 (M+H)+. HPLC (Method A) Rt 6.01 min (purity: 96.5%).

후처리

  1. temperaturethe mixture was heated at 80° C. for 18 h
  2. temperatureThe reaction mixture was cooled to RT
  3. custompartitioned between water and Et2O
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. custompurified by flash chromatography (cHex/EtOAc from 9:1 to 8:2), which

출처 및 근거

ORD 기록
ord-7e34afec57ed4bb4b2278f2b51a567f2
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202865B2

반응 노트

불러오는 중…