4-Methylmorpholine → 6-[5-(1-Anthraquinonecarbonyl)amino-1-pentanyl]-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]-hexadeca-1(16),12,14-triene

HRID 636320

Reaction equation

HRID 636320 reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][C:2]=1C(O)=O.CN1CC[O:24]CC1.[CH2:27]1[CH2:32]C[CH:30]([N:33]=[C:34]=NC2CCCCC2)[CH2:29][CH2:28]1.C1C=CC2N(O)N=NC=2C=1.[N+:52]([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[S:61]([N:64]1[CH2:78][CH2:77][NH:76][CH2:75][CH2:74][CH2:73][N:72]([S:79]([C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][C:83]=2[N+:88]([O-:90])=[O:89])(=[O:81])=[O:80])[CH2:71][C:70]2[N:91]=[C:66]([CH:67]=[CH:68][CH:69]=2)[CH2:65]1)(=[O:63])=[O:62])([O-:54])=[O:53]>C(Cl)Cl>[C:8]1([C:34]([NH:33][CH2:30][CH2:29][CH2:28][CH2:27][CH2:32][N:76]2[CH2:75][CH2:74][CH2:73][N:72]([S:79]([C:82]3[CH:87]=[CH:86][CH:85]=[CH:84][C:83]=3[N+:88]([O-:90])=[O:89])(=[O:81])=[O:80])[CH2:71][C:70]3[N:91]=[C:66]([CH:67]=[CH:68][CH:69]=3)[CH2:65][N:64]([S:61]([C:56]3[CH:57]=[CH:58][CH:59]=[CH:60][C:55]=3[N+:52]([O-:54])=[O:53])(=[O:63])=[O:62])[CH2:78][CH2:77]2)=[O:24])[C:7]2[C:6](=[O:16])[C:5]3[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=3)[C:13](=[O:15])[C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 670302-Anthraquinonecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 10555399HCID 10555399, compound

Product 1

HCID 212573426-[5-(1-Anthraquinonecarbonyl)amino-1-pentanyl]-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]-hexadeca-1(16),12,14-trieneYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of anthraquinone-2-carboxylic acid (151 mg, 0.6 mmol) and 4-methylmorpholine (91 mg, 0.9 mmol) in 10 mL of CH2Cl2 was stirred at rt for 30 min. After addition of DCC (124 mg, 0.6 mmol), HOBT (81 mg, 0.6 mmol), the solution was stirred another 30-min. A solution of 3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo-[10.3.1]hexadeca-1(16),12,14-triene (405 mg, 0.6 mmol) in 5 mL of CH2Cl2 was added to the above solution and the resulting solution was stirred for 30 h. The reaction solution was filtered and the filtrate was washed with brine, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography on a silica gel column using EtOAc as eluent to give 0.41 g (76%) of the title compound as a yellow foam. 1H NMR (CDCl3) δ 1.40-1.75 (m, 4H), 1.91-2.11 (m, 2H), 2.12-2.32 (m, 4H), 3.14-3.30 (m, 4H), 3.30-3.51 (m, 4H), 4.20-4.35 (m, 2H), 6.96-7.10 (br, 1H), 7.31-8.49 (m, 18H). HRMS (FAB) m/z 910.2506 (M+1)+ (C44H44N7O11S2 requires 910.2540). A satisfactory elemental analysis result was obtained for compound 6-[5-(1-Anthraquinonecarbonyl) amino-1-pentanyl]-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene (5) 5, a derivative of the title compound.

Workup

  1. stirringthe resulting solution was stirred for 30 h
  2. filtrationThe reaction solution was filtered
  3. washthe filtrate was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-74e731e32e1049b88fc7cb2d55874f15
Source dataset
uspto-grants-2001_02
Patent number
US06191273B1

Linked notes

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