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

반응식

HRID 636320 반응식
[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

참가 물질

7

반응물 5

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

생성물 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-triene수율 76%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-74e731e32e1049b88fc7cb2d55874f15
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06191273B1

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