Triethylamine → HCID 90006117, compound

HRID 718742Notes

Reaction equation

HRID 718742 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][C:7]1[N:8]=[C:9]2[C:14](=[C:15]3[C:20]=1[CH:19]=[CH:18][CH:17]=[CH:16]3)[CH:13]=[CH:12][CH:11]=[CH:10]2)=[O:4].[NH:21]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28][NH:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH:13]1[C:14]2[C:9](=[N:8][C:7]([CH2:6][NH:5][C:3](=[O:4])[CH2:2][N:21]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28][NH:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[C:20]3[C:15]=2[CH:16]=[CH:17][CH:18]=[CH:19]3)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 649631,4,7,10-TetraazacyclododecaneHCID 867124842-Chloro-N-(phenanthridin-6-ylmethyl)acetamide

Product 1

HCID 90006117HCID 90006117, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of the chloro 9 (20.0 mg, 70.2 μmol) in anhydrous CHCl3 (5 mL) was added to a solution of cyclen (48.4 mg, 0.281 mmol) and triethylamine (11.7 μL, 84.2 μmol) in anhydrous CHCl3 (15 mL) under N2 (g). The reaction mixture was heated to reflux under N2 (g) for 23 hours. The reaction mixture was then allowed to cool to room temperature and washed with NaOH (aq) (1.0 M, 3×5 mL) and H2O (3×5 mL). The organic phase was dried over MgSO4, and concentrated under reduced pressure yielding product 10 as a colorless oil (13.9 mg, 47.1%). This procedure follows closely that developed by Gunnlaugsson and coworkers. (Massue et al. Tetrahedron Lett., 2007, 48, 8052-8055).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux under N2 (g) for 23 hours
  3. washwashed with NaOH (aq) (1.0 M, 3×5 mL) and H2O (3×5 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7032c9cfaf014cd299a8313934d2b44b
Source dataset
uspto-grants-2015_11
Patent number
US09194802B2

Reaction notes

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