Dicyclohexylcarbodiimide → HCID 59238973, compound

HRID 1949129Notes

Reaction equation

HRID 1949129 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][C:10]([C:16]([OH:18])=[O:17])=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[C:5]2[C:19]3[CH:20]=[C:21]([C:26]([OH:28])=[O:27])[CH:22]=[CH:23][C:24]=3[NH:25][C:4]=12.C1(NC(=NC2CCCCC2)O[CH2:38][CH2:39][N:40]([CH2:43][CH3:44])[CH2:41][CH3:42])CCCCC1.C1CCC(N=[C:59]=[N:60][CH:61]2[CH2:66]CCCC2)CC1.[CH3:67][CH2:68]OC(C)=O.[CH3:73]CCCCC>CN(C=O)C.Cl[Cu]>[CH3:1][O:2][C:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][C:10]([C:16]([O:18][CH2:67][CH2:68][N:60]([CH2:59][CH3:73])[CH2:61][CH3:66])=[O:17])=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[C:5]2[C:19]3[CH:20]=[C:21]([C:26]([O:28][CH2:44][CH2:43][N:40]([CH2:39][CH3:38])[CH2:41][CH3:42])=[O:27])[CH:22]=[CH:23][C:24]=3[NH:25][C:4]=12

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 21226206Ethyl acetate hexaneHCID 22025395HCID 22025395, compoundHCID 67212214HCID 67212214, compound2×

Product 1

HCID 59238973HCID 59238973, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-methoxy-5,7-dihydroindolo[2,3-b]carbazole-2,10-dicarboxylic acid (1 g, 2.67 mmol) and 2-(diethylamino)ethyl N,N′-dicyclohexylcarbamimidate (2.6 g, 8.0 mmol) in DMF (10 mL) was stirred at room temperature for 48 h. [2-(diethylamino)ethyl N,N′-dicyclohexylcarbamimidate was prepared from DCC (1 equivelent), N,N′-diethylethanolamine (1 equivelent) and CuCl (cat.) at 135° C. under microwave for 2 h]. The reaction mixture was diluted with 50% EtOAc/Hexane and washed with water. The combined organic layer was dried (MgSO4), concentrated, purified by chromatography to provide Bis(2-(diethylamino)ethyl) 6-methoxy-5,7-dihydroindolo[2,3-b]carbazole-2,10-dicarboxylate (85-90%). 1H NMR (300 MHz, CD3OD) δ ppm 8.83 (d, J=1.4 Hz, 2H), 8.59 (s, 1H), 8.05 (dd, J=1.4, 8.5 Hz, 2H), 7.49 (d, J=8.5 Hz, 2H), 4.43 (q, J=7.3 Hz, 4H), 4.32 (m, 2H), 3.18 (m, 2H), 1.47 (t, J=7.3 Hz, 6H).

Workup

  1. washwashed with water
  2. dry with materialThe combined organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by chromatography

Sources & evidence

ORD record
ord-ce2200358913417fb56f699c08674e35
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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