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Triethylamine → 2-Chloro-5-[[2-[[2-(methylthio)ethyl]amino]ethyl]amino]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 2085650
Notes
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Reaction equation

HRID 2085650 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][S:27][CH2:28][CH2:29][NH2:30].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([NH:22][CH2:23][CH2:24][NH:30][CH2:29][CH2:28][S:27][CH3:26])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:11][CH:10]([CH2:16][CH:14]([CH2:13]3)[CH2:15]1)[CH2:9]2)=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 87697(2-(Methylthio)ethyl)amineHCID 516892Sodium BicarbonateHCID 114176532-Chloro-5-(2-chloroethyl)amino-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

Product 1

HCID 101138772-Chloro-5-[[2-[[2-(methylthio)ethyl]amino]ethyl]amino]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamideYield 56.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chloro-5-[(2-chloroethyl)amino]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.200 g, Example 29c), 2-(methylthio)ethylamine (0.478 g), triethylamine (0.7 ml) and tetrahydrofuran (4 ml) were heated together in a sealed tube at 80° C. for 24 h. The mixture was cooled, poured into saturated aqueous sodium hydrogencarbonate solution and extracted into ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified on silica gel (eluant 19:1/dichloromethane:methanol) to afford the title compound as a gum (0.129 g).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted into ethyl acetate
  3. dry with materialThe combined 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/dichloromethane:methanol)

Sources & evidence

ORD record
ord-776d93c5581f422786800515dcdad91e
Source dataset
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06720452B2

Reaction notes

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