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

HRID 219956ノート

反応式

HRID 219956 の反応式
[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

参加物

6

反応物 4

HCID 81531Diisopropylethylamine2 回HCID 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-7e34afec57ed4bb4b2278f2b51a567f2
出典データセット
uspto-grants-2012_06
特許番号
US08202865B2

反応ノート

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