Potassium Carbonate → HCID 86712485, compound

HRID 718743

Reaction equation

HRID 718743 reaction equation
[N:1]1([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][N:7]([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:6][CH2:5][N:4]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:44][C:45]([NH:47][CH2:48][C:49]1[N:50]=[C:51]2[C:56](=[C:57]3[C:62]=1[CH:61]=[CH:60][CH:59]=[CH:58]3)[CH:55]=[CH:54][CH:53]=[CH:52]2)=[O:46]>CC#N.CC#N.CN(C=O)C>[O:46]=[C:45]([NH:47][CH2:48][C:49]1[N:50]=[C:51]2[C:56](=[C:57]3[C:62]=1[CH:61]=[CH:60][CH:59]=[CH:58]3)[CH:55]=[CH:54][CH:53]=[CH:52]2)[CH2:44][N:10]1[CH2:9][CH2:8][N:7]([CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:6][CH2:5][N:4]([CH2:21][C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:3][CH2:2][N:1]([CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:12][CH2:11]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11237632Tri-tert-butyl 1,4,7,10-Tetraazacyclododecane-1,4,7-triacetateHCID 867124842-Chloro-N-(phenanthridin-6-ylmethyl)acetamide

Product 1

HCID 86712485HCID 86712485, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Procedure

Tri-tert-butyl 2,2′,2″-(1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate (33.5 mg, 65.1 mop was dissolved in dry CH3CN (10 mL) and magnetically stirred under N2(g). Anhydrous K2CO3 (30.0 mg, 0.217 mmol) was added, followed by 2-chloro-N-(phenanthridin-6-ylmethyl)acetamide (Weitz et al., J. Am. Chem. Soc., 2012, 134, 16099-16102) (15.4 mg, 54.2 mmol) dissolved in 15 mL CH3CN/DMF (2:1), and the reaction mixture was heated to reflux for 27 hours under N2(g). The reaction mixture was then filtered and concentrated under reduced pressure to yield a colorless glass that was used without further purification in the next step. 1H NMR (500 MHz, CDCl3) δ 1.45 (s, 27H), 2.70-3.21 (m, 16H), 3.37-3.42 (m, 6H), 5.41 (d, J=15 Hz, 2H), 7.66-7.87 (m, 3H), 8.02 (d, J=7.0 Hz, 1H), 8.22 8.28 (d, J=6.5 Hz, 1H), 8.55 (d, J=8.0 Hz, 1H), 8.63 (d, J=7.5 Hz, 1H), 8.77 (d, J=7.0 Hz, 1H). HRMS (ESI): calc for [C42H62N6O7]+ ([M+H]+): m/z 763.4753. found: 763.4739.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 27 hours under N2(g)
  3. filtrationThe reaction mixture was then filtered
  4. concentrationconcentrated under reduced pressure
  5. customto yield a colorless glass that
  6. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-2ead88fa8bfe460c9abc1dbc0fe05ead
Source dataset
uspto-grants-2015_11
Patent number
US09194802B2

Linked notes

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