Methanesulfonyl chloride → 3-[4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butynyl]quinoline

HRID 53640노트

반응식

HRID 53640 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]#[C:12][CH2:13][CH2:14]O)[CH:2]=1.C(N(CC)C(C)C)(C)C.CS(Cl)(=O)=O.[C:30]1([C:36]2[CH2:37][CH2:38][NH:39][CH2:40][CH:41]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)(O)[O-].[Na+]>CN(C)C1C=CN=CC=1>[C:30]1([C:36]2[CH2:41][CH2:40][N:39]([CH2:14][CH2:13][C:12]#[C:11][C:3]3[CH:2]=[N:1][C:10]4[C:5]([CH:4]=3)=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH2:38][CH:37]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

참가 물질

7

반응물 5

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 516892Sodium BicarbonateHCID 106317924-(3-Quinolinyl)-3-butyn-1-ol

생성물 1

HCID 99058843-[4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butynyl]quinoline

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

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온도
0 °C

실험 절차

A solution of the alcohol prepared in Step (a) (1.98 g, 0.01 mol), N,N-diisopropylethylamine (3.5 mL, 0.02 mol) and a catalytic amount of 4-dimethylaminopyridine is cooled to 0° C., and methanesulfonyl chloride (0.8 mL, 0.0105 mol) is added dropwise. The solution is stirred at 0° C. for 18 hours, and then concentrated under reduced pressure. The residue is taken up in dimethylformamide (20 mL), and to this solution is added 4-phenyl-1,2,3,6-tetrahydropyridine (2.41 g, 0.015 mol) and sodium bicarbonate (3.4 g, 0.04 mol). The mixture is heated at 40° C. for 5 hours, and the solvent is removed under reduced pressure. The residue is partitioned between 50 mL of ethyl acetate and 50 mL of water. The aqueous layer is extracted with 50 mL of ethyl acetate and the combined organic layers are dried (sodium sulfate), and the solvent is removed in vacuo. The residue is chromatographed (silica gel, 2% methanol/98% dichloromethane) to give the title compound, containing 0.4 mol of water; mp 94.3°-95.8° C.

후처리

  1. concentrationconcentrated under reduced pressure
  2. temperatureThe mixture is heated at 40° C. for 5 hours
  3. customthe solvent is removed under reduced pressure
  4. customThe residue is partitioned between 50 mL of ethyl acetate and 50 mL of water
  5. extractionThe aqueous layer is extracted with 50 mL of ethyl acetate
  6. dry with materialthe combined organic layers are dried (sodium sulfate)
  7. customthe solvent is removed in vacuo
  8. customThe residue is chromatographed (silica gel, 2% methanol/98% dichloromethane)

출처 및 근거

ORD 기록
ord-504a69a74ede4598b2f28cab21a8b610
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620988

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