Potassium Carbonate → HCID 68465699, 화합물

HRID 131226노트

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HRID 131226 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18](F)[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:15]=2[F:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[F:31][C:32]([F:43])([F:42])[O:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=1>CN(C=O)C.ClCCl.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([NH:39][CH2:38][C:37]3[CH:40]=[CH:41][C:34]([O:33][C:32]([F:31])([F:42])[F:43])=[CH:35][CH:36]=3)[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:15]=2[F:24])[CH2:10][CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 5718464-(Trifluoromethoxy)benzylamineHCID 66712179HCID 66712179, 화합물

생성물 1

HCID 68465699HCID 68465699, 화합물수율 80.3%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 6344Dichloromethane용매

실험 절차

8 g of 4-(2,5-difluoro-4-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (23 mmol) and 3.82 g potassium carbonate (27.65 mmol) were suspended in 80 ml DMF under stirring and then treated dropwise within 10 min with a solution of 5.29 g of 4-trifluoromethoxy-benzylamine (27.65 mmol) in 30 ml DMF. The reaction mixture was then stirred for 48 h at rt, diluted with 500 ml dichloromethane and 1 liter of water. After separation, the organic phase was washed with brine (500 ml). The two aqueous phases were then reextracted with 2×250 ml dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated in vacuo. The solid residue was stirred with 150 ml heptane/ethylacetate 4:1. After 10 minutes the suspension was diluted with 100 ml heptane, and after additional 10 min stirring, filtered. After drying in vacuo, 9.5 g of 4-[2-fluoro-4-nitro-5-(4-trifluoromethoxy-benzylamino)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester was obtained as a yellow solid (80%). MS(ISP): 515.3 (M+H)+.

후처리

  1. stirringThe reaction mixture was then stirred for 48 h at rt
  2. customAfter separation
  3. washthe organic phase was washed with brine (500 ml)
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. stirringThe solid residue was stirred with 150 ml heptane/ethylacetate 4:1
  8. additionAfter 10 minutes the suspension was diluted with 100 ml heptane
  9. stirringafter additional 10 min stirring
  10. filtrationfiltered
  11. customAfter drying in vacuo

출처 및 근거

ORD 기록
ord-f932251f261f4026a334df9d14d9d324
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384945B2

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