Potassium Carbonate → methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracen-9-yl)-4-amino-1H-imidazole-5-carboxylate

HRID 1650999

反応式

HRID 1650999 の反応式
[CH2:1]1[CH:14]2[CH:5]([CH2:6][C:7]3[C:12]([CH:13]2[NH:15][CH:16]=[N:17][C:18]#[N:19])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:4][CH2:3][CH2:2]1.[C:20](=O)([O-])[O-].[K+].[K+].Br[CH:27](C)[C:28]([O-:30])=[O:29]>CN(C)C=O.C1OCCOCCOCCOCCOCCOC1>[CH2:1]1[CH:14]2[CH:5]([CH2:6][C:7]3[C:12]([CH:13]2[N:15]2[C:27]([C:28]([O:30][CH3:20])=[O:29])=[C:18]([NH2:19])[N:17]=[CH:16]2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 14535398Alpha-bromopropionateHCID 178512230HCID 178512230、化合物

生成物 1

HCID 23050704methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracen-9-yl)-4-amino-1H-imidazole-5-carboxylate収率 43%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 2855718-Crown-6溶媒

実験手順

20.8 Parts of N-(1,2,3,4,4a,9,9a,10-octahydroanthracene-9-yl)-N'-cyano-formamidine were dissolved in 140 ml of N,N-dimethylformamide together with 0.1 parts of 18-crown-6. 28.4 Parts of potassium carbonate were added. The mixture was heated to +80° C. and 13.8 Parts of α-bromo-methyl-acetate were added. After 15 hours at +80° C. to +100° C. the reactants were poured on ice and the mixture was extracted with ether. The etheral extracts were dried with Na2SO4, filtered and concentrated. 21 Parts of crude residue were chromatographed on a silica gel column and extracted with an ethyl acetate/hexane mixture (1:1). 11.6 Parts (43%) of methyl 1-(1,2,3,4,4a,9,9a,10-octahydroanthracene-9-yl)-4amino-1H-imidazole-5-carboxylate (int. 15), mp. 155-159° C. were isolated.

後処理

  1. temperatureThe mixture was heated to +80° C.
  2. additionAfter 15 hours at +80° C. to +100° C. the reactants were poured on ice
  3. extractionthe mixture was extracted with ether
  4. dry with materialThe etheral extracts were dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custom21 Parts of crude residue were chromatographed on a silica gel column
  8. extractionextracted with an ethyl acetate/hexane mixture (1:1)

出典と根拠

ORDレコード
ord-8602da9df2cb4871b69c1d96b50b5e72
出典データセット
uspto-grants-1990_05
特許番号
US04927449

関連ノート

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