1,2-Dibromoethane → Dibenzyl-[2,4-difluoro-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-phenyl]-amine

HRID 38107노트

반응식

HRID 38107 반응식
[CH2:1]([N:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:9]1[C:10]([F:28])=[C:11]([C:16]2[C:17]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[C:18]([SH:21])[NH:19][N:20]=2)[C:12]([F:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:43][CH2:44]Br>CN(C=O)C>[CH2:29]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C:16]2[C:17]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[C:18]3[S:21][CH2:43][CH2:44][N:19]3[N:20]=2)[C:10]=1[F:28])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

참가 물질

5

반응물 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 178505870HCID 178505870, 화합물

생성물 1

HCID 58477092Dibenzyl-[2,4-difluoro-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-phenyl]-amine수율 40.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5-(3-Dibenzylamino-2,6-difluoro-phenyl)-4-pyridin-4-yl-2H-pyrazole-3-thiol (1.26 g, 2.6 mmol) was dissolved in dry DMF (33 mL) under nitrogen atmosphere. Solid potassium carbonate (1.8 g, 13 mmol, 5 eq) was added followed by 1,2-dibromoethane (0.252 mL, 2.86 mmol, 1.1 eq) and the suspension was stirred at room temperature for 4 hours. DMF was then removed under reduced pressure and the residue was partitioned between saturated aqueous NaHCO3 and ethyl acetate. The organic phase was washed with brine, dried over Na2SO4 and evaporated to dryness. 537 mg of dibenzyl-[2,4-difluoro-3-(7-pyridin-4-yl-2,3-dihydro-pyrazolo[5,1-b]thiazol-6-yl)-phenyl]-amine were obtained as white solid (47% over 2 steps).

후처리

  1. customDMF was then removed under reduced pressure
  2. customthe residue was partitioned between saturated aqueous NaHCO3 and ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

출처 및 근거

ORD 기록
ord-2cecd265eb72433db66bed924129f72c
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524707B2

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