Potassium Carbonate → HCID 90403025, 화합물

HRID 2200714노트

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HRID 2200714 반응식
Br[C:2]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]2[C:8](=[O:19])[N:7]([CH2:20][CH2:21][CH2:22][OH:23])[C:6](=[O:24])[N:5]([CH3:25])[C:4]=2[N:3]=1.[Cl:26][C:27]1[CH:28]=[C:29]([OH:38])[CH:30]=[C:31]([O:33][C:34]([F:37])([F:36])[F:35])[CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:26][C:27]1[CH:28]=[C:29]([CH:30]=[C:31]([O:33][C:34]([F:35])([F:36])[F:37])[CH:32]=1)[O:38][C:2]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]2[C:8](=[O:19])[N:7]([CH2:20][CH2:21][CH2:22][OH:23])[C:6](=[O:24])[N:5]([CH3:25])[C:4]=2[N:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 467376533-Chloro-5-(trifluoromethoxy)phenolHCID 904024698-bromo-7-(4-chlorobenzyl)-1-(3-hydroxypropyl)-3-methyl-3,7-dihydro-1H-purine-2,6-dione2회

생성물 1

HCID 90403025HCID 90403025, 화합물수율 53.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

To a solution of the 8-bromo-7-(4-chlorobenzyl)-1-(3-hydroxypropyl)-3-methyl-1H-purine-2,6(3H,7H)— dione (50 mg, 0.116 mmol, intermediate 63) in DMF (2 mL) was added 3-chloro-5-(trifluoromethoxy)phenol (29.82 mg, 0.140 mmol) followed by potassium carbonate (24.24 mg, 0.175 mmol). The reaction was stirred at 85° C. for 2 h. The reaction was cooled and partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give crude product, which was purified by preparative HPLC to give 8-(3-chloro-5-(trifluoromethoxy)phenoxy)-7-(4-chlorobenzyl)-1-(3-hydroxypropyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (35 mg, 53.5% yield) as white solid. 1H-NMR (CD3OD) δ 7.458-7.435(m,3H), 7.381-7.365(m,3H), 7.361(s,1H), 5.507(s,2H), 4.138-4.102(t,2H), 3.640-3.608(t,2H), 3.448(s,3H), 1.905-1.871(m,2H). LCMS retention time 3.325 min; LCMS MH+ 559.

후처리

  1. temperatureThe reaction was cooled
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give crude product, which
  8. customwas purified by preparative HPLC

출처 및 근거

ORD 기록
ord-1c8da4d3d90f449abcb309e3d1c7677b
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359359B2

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