Water → 9-tert-butyl-3-methoxy-2-bromo-14-chloro-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one

HRID 1971735노트

반응식

HRID 1971735 반응식
[C:1]([N:5]1[CH2:26][CH2:25][CH2:24][CH2:23][C:8]2[CH:9]=[C:10]3[C:19]4[CH:18]=[C:17]([Br:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:27])([CH3:4])([CH3:3])[CH3:2].[Cl:28]N1C(=O)CCC1=O.O>CN(C=O)C.[O-]S([O-])(=S)=O.[Na+].[Na+]>[C:1]([N:5]1[CH2:26][CH2:25][CH2:24][CH2:23][C:8]2[C:9]([Cl:28])=[C:10]3[C:19]4[CH:18]=[C:17]([Br:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:27])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 58124845HCID 58124845, 화합물

생성물 1

HCID 581249549-tert-butyl-3-methoxy-2-bromo-14-chloro-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one수율 91.2%

시약·촉매·용매 2

HCID 24477Sodium Thiosulfate촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 66 mg of 19d in 1 ml of DMF was added at 0° C. 27 mg of N-chlorosuccinimide. The mixture was stirred for 2 h. Then, 5 ml of water was added and 1 drop of a sat. Na2S2O3 solution. Stirring was continued for 5 min and the product was extracted into ethyl acetate. The extract was washed with water, dried, concentrated and the residue was treated with cold pentane, to provide 65 mg of 19e as a white crystalline material; Mp 203-205° C. MS-ESI: [M+1] 464.12, 465.10, 466.09, 467.08, 468.08 and 469.07.

후처리

  1. stirringStirring
  2. waitwas continued for 5 min
  3. extractionthe product was extracted into ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated
  7. additionthe residue was treated with cold pentane

출처 및 근거

ORD 기록
ord-e3f9961a01af4a5ea07992c330566ff2
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431564B2

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