Bicarbonate Ion → 2-Chloro-5-[[2-[[2-(1-methyl-1H-imidazol-5-yl)ethyl]amino]ethyl]amino]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 2085652노트

반응식

HRID 2085652 반응식
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([NH:22][CH2:23][CH2:24]Cl)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[CH3:26][N:27]1[C:31]([CH2:32][CH2:33][NH2:34])=[CH:30][N:29]=[CH:28]1.C(N(CC)C(C)C)(C)C.[I-].[K+].[Na].C(=O)([O-])O>C(O)CCC>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([NH:22][CH2:23][CH2:24][NH:34][CH2:33][CH2:32][C:31]2[N:27]([CH3:26])[CH:28]=[N:29][CH:30]=2)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]

참가 물질

8

반응물 6

HCID 769Bicarbonate IonHCID 4875Potassium IodideHCID 695203-MethylhistamineHCID 81531DiisopropylethylamineHCID 5360545SodiumHCID 114176532-Chloro-5-(2-chloroethyl)amino-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

생성물 1

HCID 102270742-Chloro-5-[[2-[[2-(1-methyl-1H-imidazol-5-yl)ethyl]amino]ethyl]amino]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide수율 43%

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

2-Chloro-5-[(2-chloroethyl)amino]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (Example 29c, 0.100 g), 3-methylhistamine (0.200 g), N,N-diisopropylethylamine (0.5 ml), potassium iodide (0.040 g) and n-butanol (4 ml) were heated together in a sealed tube at 110° C. for 24 h. The solution was cooled, poured into saturated aqueous sodium to hydrogencarbonate solution and extracted into ethyl acetate. The extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified on silica gel (eluant 19:1:0.1 dichloromethane/methanol/ammonia) to afford the title compound as a gum (0.053 g).

후처리

  1. temperatureThe solution was cooled
  2. extractionextracted into ethyl acetate
  3. dry with materialThe extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified on silica gel (eluant 19:1:0.1 dichloromethane/methanol/ammonia)

출처 및 근거

ORD 기록
ord-e26e1cfc620e49818caebf3f29c90281
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06720452B2

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