Azetidine → 2-[2-(1-Azetidinyl)ethyl]-7-chloro-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one oxalate

HRID 4863

반응식

HRID 4863 반응식
[Cl:1][C:2]1[CH:12]=[N:11][C:10]2[O:9][CH:8]([CH2:13][CH2:14]Cl)[CH2:7][N:6]([CH3:16])[C:5](=[O:17])[C:4]=2[CH:3]=1.[C:18](=[O:21])([O-:20])[O-].[K+].[K+].[NH:24]1[CH2:27][CH2:26][CH2:25]1.[OH-:28].[NH4+]>CS(C)=O.O.CO.C(OCC)(=O)C>[C:5]([OH:17])(=[O:28])[C:18]([OH:20])=[O:21].[N:24]1([CH2:14][CH2:13][CH:8]2[CH2:7][N:6]([CH3:16])[C:5](=[O:17])[C:4]3[CH:3]=[C:2]([Cl:1])[CH:12]=[N:11][C:10]=3[O:9]2)[CH2:27][CH2:26][CH2:25]1

참가 물질

9

반응물 4

HCID 10422Azetidine3회HCID 11430Potassium CarbonateHCID 14923Ammonium HydroxideHCID 137264457-Chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-one

생성물 1

HCID 137266002-[2-(1-Azetidinyl)ethyl]-7-chloro-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one oxalate

시약·촉매·용매 4

HCID 679Dimethyl Sulfoxide용매HCID 887Methanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 6 g (0.022 mole) of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-one in 40 ml of dimethyl sulfoxide was added 8.0 g of crushed potassium carbonate and 1.5 g (0.026 mole) of azetidine. The reaction was stirred at room temperature for 24 hr. After checking ty TLC [7:2:1 by volume ethyl acetate:methanol:conc. ammonium hydroxide, another 0.4 g (0.007 mole) of azetidine was added. Two days later, another 0.5 g (0.0087 mole) of azetidine was added and the mixture stirred for 24 hr more. The reaction mixture was diluted with 100 ml of water and extracted with 4×100 ml of benzene. The organic extracts were combined, washed with 3×100 ml of water, dried over sodium sulfate, filtered, and concentrated by rotary evaporation. The syrupy residue was treated with oxalic acid in isopropyl alcohol. This yielded 4.2 g (56.5%) of white material, m.p. 169°-174° C. with decomposition.

후처리

  1. stirringthe mixture stirred for 24 hr more
  2. extractionextracted with 4×100 ml of benzene
  3. washwashed with 3×100 ml of water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. additionThe syrupy residue was treated with oxalic acid in isopropyl alcohol

출처 및 근거

ORD 기록
ord-c8d4455c6b164a84bffaf46314b5819e
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04727152

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