Sodium Hydroxide → 2-(1-methylethyl)cyclohepta[d]imidazol-4(1H)-one

HRID 1946466

반응식

HRID 1946466 반응식
[OH-].[Na+].CC1C=CC(S(O[C:14]2[C:20](=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=O)=O)=CC=1.[CH3:22][CH:23]([C:25]([NH2:27])=[NH:26])[CH3:24].Cl.[NH4+].[Cl-]>O.C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:22][CH:23]([C:25]1[NH:27][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:20](=[O:21])[C:14]=2[N:26]=1)[CH3:24]

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 562886Tropolone TosylateHCID 27820532-Methylpropanimidamide hydrochloride

생성물 1

HCID 116870252-(1-methylethyl)cyclohepta[d]imidazol-4(1H)-one수율 100.7%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
30 °C

실험 절차

To a mixture of sodium hydroxide 30% in water (24 g) and toluene (30 mL), tropolone tosylate (5 g), isopropylcarbamidine hydrochloride (2.2 g) and tetrabutylammonium bromide (2.3 g) were added successively and the RM was stirred and heated at 30° C. for 1 hour. The reaction mixture was cooled down to room temp, diluted with an excess of sat. aq. NH4Cl solution and then extracted with EtOAc (3×40 ml). The aqueous phase was again extracted with EtOAc (3×50 ml). All the organics were combined, dried (hydrophobic frit) and concentrated under vacuum. The residue was purified by reverse phase chromatography using an acetonitrile-0.1% TFA:Water-0.1% TFA 5%-50% gradient and a 50%-95% gradient. The desired fractions were combined and concentrated under vacuum to yield the title compound (3.4 g). LC/MS MH+ 189, Rt 1.18 min (5 minute run)

후처리

  1. additionwere added successively
  2. temperatureThe reaction mixture was cooled down to room temp
  3. extractionextracted with EtOAc (3×40 ml)
  4. extractionThe aqueous phase was again extracted with EtOAc (3×50 ml)
  5. customdried (hydrophobic frit)
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by reverse phase chromatography
  8. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-e564a288b51141cbb929d70d96eb9aa7
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399444B2

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