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 2085652Notes

Reaction equation

HRID 2085652 reaction equation
[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]

Participants

8

Reactant 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

Product 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)-benzamideYield 43%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-e26e1cfc620e49818caebf3f29c90281
Source dataset
uspto-grants-2004_04
Patent number
US06720452B2

Reaction notes

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