1,4,7,10-Tetraazacyclododecane → HCID 57816368, compound

HRID 383195Notes

Reaction equation

HRID 383195 reaction equation
[NH:1]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:13]([O:20][C:21](=[O:38])[CH:22](Br)[CH2:23][CH2:24][CH2:25][N:26]1[C:34](=[O:35])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]1=[O:36])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC#N>[CH2:13]([O:20][C:21](=[O:38])[CH:22]([N:1]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)[CH2:23][CH2:24][CH2:25][N:26]1[C:27](=[O:36])[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:34]1=[O:35])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 649631,4,7,10-TetraazacyclododecaneHCID 58731563HCID 58731563, compound

Product 1

HCID 57816368HCID 57816368, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

55 g of cyclen base (320 mmol) are dissolved in 550 ml of CH3CN, to which 119.8 g of brominated derivative (2-bromo-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acid benzyl ester, 288 mmol) dissolved in 550 ml of CH3CN are added dropwise. The medium is stirred at ambient temperature overnight. The precipitate is filtered off and washed thoroughly with acetonitrile. 138 g of product are obtained in the form of a white powder (corrected yield 81.3%).

Workup

  1. additionare added dropwise
  2. filtrationThe precipitate is filtered off
  3. washwashed thoroughly with acetonitrile

Sources & evidence

ORD record
ord-9c57dc03620d4654bfc3504b55ad2625
Source dataset
uspto-grants-2013_02
Patent number
US08367039B2

Reaction notes

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