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

HRID 2288992노트

반응식

HRID 2288992 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d57a526d96084f2eb2bdb0037994045c
출처 데이터셋
uspto-grants-2000_07
특허 번호
US06090825

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