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

HRID 1946466

反応式

HRID 1946466 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
30 °C

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-e564a288b51141cbb929d70d96eb9aa7
出典データセット
uspto-grants-2013_03
特許番号
US08399444B2

関連ノート

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