Morpholine → 4-{4-[4-(5-Bromo-pyridin-2-yl)-but-3-ynyl]-benzyl}-morpholine

HRID 1916540

반응식

HRID 1916540 반응식
CS(Cl)(=O)=O.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[C:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23]O)=[CH:19][CH:18]=2)=[N:11][CH:12]=1.C(N(C(C)C)C(C)C)C.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>C(Cl)Cl>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[C:14][CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:21][CH:22]=2)=[N:11][CH:12]=1

참가 물질

6

반응물 4

HCID 8083MorpholineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 69070552{4-[4-(5-Bromo-pyridin-2-yl)-but-3-ynyl]-phenyl}-methanol

생성물 1

HCID 690796844-{4-[4-(5-Bromo-pyridin-2-yl)-but-3-ynyl]-benzyl}-morpholine

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

36 μL (0.46 mmol) methanesulphonic acid chloride are added to a solution, cooled to 0° C., of 120 mg (0.38 mmol) {4-[4-(5-bromo-pyridin-2-yl)-but-3-ynyl]-phenyl}-methanol (Example 2.20a) in 5 mL DCM. A solution of 78 μL (0.46 mmol) ethyldiisopropylamine in 1 mL DCM is slowly added dropwise, the mixture is stirred for a further 30 min at 0° C., then 80 μL (0.92 mmol) of morpholine are added, the mixture is allowed to come up to RT and kept at RT for 2 h. The mixture is evaporated down i. vac., the residue is combined with 20 mL EtOAc and 10 mL water, acidified with 1 M HCl and the phases are separated. The aqueous phase is combined with 2 M Na2CO3 solution, extracted with 20 mL EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the product is obtained.

후처리

  1. customto come up to RT
  2. waitkept at RT for 2 h
  3. customThe mixture is evaporated down i
  4. customthe phases are separated
  5. extractionextracted with 20 mL EtOAc
  6. dry with materialthe organic phase is dried over Na2SO4
  7. customis obtained

출처 및 근거

ORD 기록
ord-a975bf584ea84da5ab7f977f3b368b43
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618132B2

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