Ethanol → 2-(Methylamino)-2-oxoethyl 4-(5-{4-[(trifluoro-methyl)oxy]phenyl}-2-pyridyl)-1,4-diazepane-1-carboxylate

HRID 2246226노트

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HRID 2246226 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]([NH:21][CH3:22])=[O:20])=[O:16])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[F:23][C:24]([F:36])([F:35])[O:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1>[F:23][C:24]([F:35])([F:36])[O:25][C:26]1[CH:31]=[CH:30][C:29]([C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]([NH:21][CH3:22])=[O:20])=[O:16])[CH2:10][CH2:9]3)=[N:6][CH:7]=2)=[CH:28][CH:27]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 602095672-(Methylamino)-2-oxoethyl 4-(5-bromo-2-pyridyl)-1,4-diazepane-1-carboxylate

생성물 1

HCID 592182162-(Methylamino)-2-oxoethyl 4-(5-{4-[(trifluoro-methyl)oxy]phenyl}-2-pyridyl)-1,4-diazepane-1-carboxylate수율 57.5%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
150 °C

실험 절차

0.12 g (0.3 mmol) of 2-(methylamino)-2-oxoethyl 4-(5-bromo-2-pyridyl)-1,4-diazepane-1-carboxylate, prepared in step 11.3., 0.25 g (1.2 mmol) of 4-(trifluoromethoxy)-phenylboronic acid and 0.9 ml (1.8 mmol) of aqueous sodium carbonate solution (2M), suspended in 3.5 ml of toluene and 0.8 ml of ethanol are introduced into a Pyrex reactor. 0.07 g (0.06 mmol) of tetrakis-(triphenylphosphine)palladium is then added and, after sealing the reactor, it is maintained at 150° C. for 15 minutes under microwave irradiation. The organic phase is recovered after separation of the phases by settling, and the filtrate is concentrated under reduced pressure. The residue thus obtained is purified by chromatography on silica gel, eluting with a 30/70/5 mixture of ethyl acetate, cyclohexane and methanol. After crystallization from diisopropyl ether, 0.078 g of product is obtained in the form of a white solid.

후처리

  1. customThe organic phase is recovered
  2. customafter separation of the phases
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue thus obtained
  5. customis purified by chromatography on silica gel
  6. washeluting with a 30/70/5 mixture of ethyl acetate, cyclohexane and methanol
  7. customAfter crystallization from diisopropyl ether

출처 및 근거

ORD 기록
ord-b83348b615f14da28ef87f546705988d
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687503B2

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