1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → tert-butyl 2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxoethylcarbamate

HRID 1162293ノート

反応式

HRID 1162293 の反応式
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[CH3:36][C:37]1[N:41]2[C:42](=[O:51])[N:43]([CH:45]3[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]3)[CH2:44][C:40]2=[CH:39][N:38]=1.C1CCN2C(=NCCC2)CC1>C(#N)C.C(N(CC)CC)C>[CH3:36][C:37]1[N:41]2[C:42](=[O:51])[N:43]([CH:45]3[CH2:50][CH2:49][N:48]([C:10](=[O:12])[CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH2:47][CH2:46]3)[CH2:44][C:40]2=[CH:39][N:38]=1

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 230840945-methyl-2-(4-piperidinyl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one dihydrochloride

生成物 1

HCID 23138308tert-butyl 2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxoethylcarbamate収率 66%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 8471Triethylamine溶媒

実験手順

To a solution of Boc-glycine (0.44 g) and HOBt (0.58 g) in acetonitrile (15 ml) was added WSC (0.72 g), and the reaction mixture was mixed at room temperature for 15 minutes. Then, a solution of 5-methyl-2-(4-piperidinyl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one dihydrochloride (0.73 g), DBU (0.75 ml) and triethylamine (1.1 ml) in acetonitrile (5 ml) was added thereto. The reaction mixture was mixed at room temperature for 15 hours, the solvent was then distilled off under reduced pressure, and the residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with an aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified with basic silica gel column (ethyl acetate to ethyl acetate/methanol=5/1) to obtain the title compound as a colorless solid (0.62 g, 66%).

後処理

  1. additionthe reaction mixture was mixed at room temperature for 15 minutes
  2. additionThe reaction mixture was mixed at room temperature for 15 hours
  3. distillationthe solvent was then distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with an aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified with basic silica gel column (ethyl acetate to ethyl acetate/methanol=5/1)

出典と根拠

ORDレコード
ord-9bcfd761a1764633b915e5172b4cf5ec
出典データセット
uspto-grants-2010_10
特許番号
US07820673B2

反応ノート

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