Boron trifluoride etherate → HCID 178513156, 화합물

HRID 2203327노트

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HRID 2203327 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9](=O)[CH2:10][CH2:11][C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14].[C:20]([NH:23][NH2:24])([NH2:22])=[NH:21].Cl.B(F)(F)F.CCOCC>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1/[C:9](=[N:24]/[NH:23][C:20](=[NH:21])[NH2:22])/[CH2:10][CH2:11][C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14]

참가 물질

5

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HCID 8000Boron trifluoride etherateHCID 866789671-(2-Bromo-5-chlorophenyl)-4,4,5,5,5-pentafluoropentan-1-oneHCID 178418668HCID 178418668, 화합물

생성물 1

HCID 178513156HCID 178513156, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

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온도
100 °C

실험 절차

To a screw cap pressure vessel was added the intermediate from Step B (0.450 g, 1.2 mmol), aminoguanidine hydrochloride (0.456 g, 6.2 mmol), methanol (20 mL) and boron trifluoride diethyl etherate (0.94 mL, 7.4 mmol). The reaction solution was heated at 100° C. for 3 hours. The solution was concentrated and the residue partitioned between EtOAc and aqueous 1N NaOH. The organic phase was washed twice with aqueous 1N NaOH and brine (1×). The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to give the indicated compound as a mixture of E,Z hyrazone isomers. 1H NMR (500 MHz, CH3OH-d4): δ 7.60 (d, J=8.6 Hz, 1H); 7.26-7.23 (m, 1H); 7.18 (d, J=2.5 Hz, 1H); 2.74 (s, 2H); 2.56 (s, 2H). m/z=421.2 (M+H).

후처리

  1. customTo a screw cap pressure vessel
  2. concentrationThe solution was concentrated
  3. customthe residue partitioned between EtOAc and aqueous 1N NaOH
  4. washThe organic phase was washed twice with aqueous 1N NaOH and brine (1×)
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the indicated compound
  9. additionas a mixture of E,Z hyrazone isomers

출처 및 근거

ORD 기록
ord-04af3ed8111f40aa97bd75802e5ce216
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365574B2

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