Morpholine → 4-{4-[3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-benzyl}-morpholine

HRID 623666

반응식

HRID 623666 반응식
CS(Cl)(=O)=O.[CH2:6]([O:13][C:14]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17]([CH:28]([CH3:30])[CH3:29])=[CH:16][C:15]=1[N:31]1[C:35]([C:36]2[CH:41]=[CH:40][C:39]([CH2:42]O)=[CH:38][CH:37]=2)=[CH:34][N:33]=[N:32]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1>C(Cl)Cl.CN(C=O)C>[CH2:6]([O:13][C:14]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:17]([CH:28]([CH3:30])[CH3:29])=[CH:16][C:15]=1[N:31]1[C:35]([C:36]2[CH:41]=[CH:40][C:39]([CH2:42][N:44]3[CH2:49][CH2:48][O:47][CH2:46][CH2:45]3)=[CH:38][CH:37]=2)=[CH:34][N:33]=[N:32]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

참가 물질

6

반응물 3

HCID 8083MorpholineHCID 31297Methanesulfonyl chlorideHCID 67985193{4-[3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-phenyl}-methanol

생성물 1

HCID 679854174-{4-[3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-benzyl}-morpholine수율 80%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

TEA (160 μl, 1.17 mmol) and MsCl (90 μl, 1.17 mmol) were added to a solution of {4-[3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-phenyl}-methanol (200 mg, 0.39 mmol) in DCM (5 ml) at 0° C. The solution was stirred for 30 minutes at 0° C. and for 12 hours at RT. The solvent was removed under reduced pressure and the reaction crude was dissolved in DMF (3 ml). Morpholine (1.17 mmol) and TEA (160 μl, 1.17 mmol) were added and the reaction mixture was stirred for 12 hours at RT. After standard work-up with AcOEt (4×30 ml) and washing with H2O (2×30 mL) and brine (2×30 ml), the solvent was evaporated under reduced pressure and the crude reaction mixture was purified by column chromatography (PE/AcOEt:20/80) to obtain the desired adduct as an oil.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe reaction crude
  3. stirringthe reaction mixture was stirred for 12 hours at RT
  4. washAfter standard work-up with AcOEt (4×30 ml) and washing with H2O (2×30 mL) and brine (2×30 ml)
  5. customthe solvent was evaporated under reduced pressure
  6. customthe crude reaction mixture
  7. customwas purified by column chromatography (PE/AcOEt:20/80)

출처 및 근거

ORD 기록
ord-c8c63ff405f8485cbd1e1dae2b349f79
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09302998B2

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