Diisopropylethylamine → 3-[2-[4-[5-Phenyl-4-[(2,2,2-trifluoroethoxy)methyl]oxazol-2-yl]piperidino]ethyl]-6-methoxybenzenesulfonamide

HRID 2288992ノート

反応式

HRID 2288992 の反応式
[C:1]1([C:7]2[O:11][C:10]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[N:9][C:8]=2[CH2:18][O:19][CH2:20][C:21]([F:24])([F:23])[F:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:26][CH2:27][C:28]1[CH:29]=[CH:30][C:31]([O:38][CH3:39])=[C:32]([S:34]([NH2:37])(=[O:36])=[O:35])[CH:33]=1.N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1.CCN(C(C)C)C(C)C>O1CCOCC1>[CH3:39][O:38][C:31]1[CH:30]=[CH:29][C:28]([CH2:27][CH2:26][N:15]2[CH2:16][CH2:17][CH:12]([C:10]3[O:11][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[C:8]([CH2:18][O:19][CH2:20][C:21]([F:22])([F:23])[F:24])[N:9]=3)[CH2:13][CH2:14]2)=[CH:33][C:32]=1[S:34]([NH2:37])(=[O:36])=[O:35]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 1859152-NaphthylalanineHCID 187004435-(2-Chloroethyl)-2-methoxy-benzenesulfonamideHCID 187004502-(4-Piperidinyl)-4-(2,2,2-trifluoroethoxymethyl)-5-phenyloxazole

生成物 1

HCID 187004673-[2-[4-[5-Phenyl-4-[(2,2,2-trifluoroethoxy)methyl]oxazol-2-yl]piperidino]ethyl]-6-methoxybenzenesulfonamide

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To 4-[5-phenyl-4-(2,2,2-trifluoro-ethoxymethyl)-oxazol-2-yl]-piperidine (0.750 g), prepared as in Intermediate 5, in dioxane is added 5-(2-chloro-ethyl)-2-methoxy-benzenesulfonamide (0.716 g), prepared as in Intermediate 1, Nal (0.429 g) and DIEA (1.15 ml). After heating at 100° C. for 18 hours, the reaction mixture is partitioned between EtOAc and dilute NaHCO3 solution. The organic phase is washed with saturated brine, dried (NaSO4) and concentrated. The residue is dissolved in CHCl3 (20 mL) and preadsorbed onto silica gel. Purification by flash chromatography on silica gel using a MeOH-EtOAc gradient (2-10%), followed by radial chromotography using a MeOH-CH2Cl2 gradient (1-5%) and crystallization from CH2Cl2 -EtOAc affords the title compound as a white solid.

後処理

  1. customthe reaction mixture is partitioned between EtOAc and dilute NaHCO3 solution
  2. washThe organic phase is washed with saturated brine
  3. dry with materialdried (NaSO4)
  4. concentrationconcentrated
  5. dissolutionThe residue is dissolved in CHCl3 (20 mL)
  6. customPurification by flash chromatography on silica gel using a MeOH-EtOAc gradient (2-10%)
  7. customa MeOH-CH2Cl2 gradient (1-5%) and crystallization from CH2Cl2 -EtOAc

出典と根拠

ORDレコード
ord-d57a526d96084f2eb2bdb0037994045c
出典データセット
uspto-grants-2000_07
特許番号
US06090825

反応ノート

読み込み中…