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Methane → 9-[5-(3-{4-[Bis(2-chloroethyl)amino]phenyl}ureido)-2-methyl-phenylamino]-5-methyl-acridine-4-carboxylic acid (2-dimethylaminoethyl)amide

HRID 1514807
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1514807
Cl.Cl.[Cl:3][CH2:4][CH2:5][N:6]([CH2:14][CH2:15][Cl:16])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1.C.O=C(Cl)[O:20][C:21](Cl)(Cl)Cl.[CH3:26][N:27]([CH3:57])[CH2:28][CH2:29][NH:30][C:31]([C:33]1[C:46]2[C:37](=[C:38]([NH:48][C:49]3[CH:54]=[C:53]([NH2:55])[CH:52]=[CH:51][C:50]=3[CH3:56])[C:39]3[C:44]([N:45]=2)=[C:43]([CH3:47])[CH:42]=[CH:41][CH:40]=3)[CH:36]=[CH:35][CH:34]=1)=[O:32]>O1CCOCC1.CN(C=O)C.N1C=CC=CC=1>[CH3:57][N:27]([CH3:26])[CH2:28][CH2:29][NH:30][C:31]([C:33]1[C:46]2[C:37](=[C:38]([NH:48][C:49]3[CH:54]=[C:53]([NH:55][C:21]([NH:13][C:10]4[CH:11]=[CH:12][C:7]([N:6]([CH2:14][CH2:15][Cl:16])[CH2:5][CH2:4][Cl:3])=[CH:8][CH:9]=4)=[O:20])[CH:52]=[CH:51][C:50]=3[CH3:56])[C:39]3[C:44]([N:45]=2)=[C:43]([CH3:47])[CH:42]=[CH:41][CH:40]=3)[CH:36]=[CH:35][CH:34]=1)=[O:32]
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Komponenten

8

Edukt 4

HCID 297MethaneHCID 10426DiphosgeneHCID 111778369-(5-Amino-2-methyl-phenylamino)-5-methylacridine-4-carboxylic acid (2-dimethylaminoethyl)amideHCID 21276262N1,N1-bis(2-chloroethyl)benzene-1,4-diamine dihydrochloride

Produkt 1

HCID 250198579-[5-(3-{4-[Bis(2-chloroethyl)amino]phenyl}ureido)-2-methyl-phenylamino]-5-methyl-acridine-4-carboxylic acid (2-dimethylaminoethyl)amide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
92.5 °C

Versuchsvorschrift

To a suspension of N,N-bis(2-chloroethyl)benzene-1,4-diamine hydrochloride (37) (0.918 g, 3 mmol) and charcoal (20 mg) in dry dioxane (30 mL) was added diphosgene (0.494 g, 2.5 mmol). The reaction mixture was heated at 90-95° C. for 5 h. After cooling, the reaction mixture was filtered through a pad of Celite and the filtrate containing crude mustard isocyanate 39 was added dropwise into the solution of 9-(5-amino-2-methyl-phenylamino)-5-methylacridine-4-carboxylic acid (2-dimethylaminoethyl)amide (0.732 g, 1.7 mmol)33 in dry DMF (25 mL) containing pyridine (2 mL) at −10° C. and then stirred at room temperature for 24 h. The solvent removed under reduced pressure to dryness and the residue was dissolved in a mixture of CHCl3/MeOH containing silica gel (10 gm) and evaporated in vacuo to dryness. The residue was put on the top of a silica gel column (4×30 cm) and chromatographed using CHCl3/MeOH (100:5 v/v) as eluent. The fractions containing the main product were combined and evaporated in vacuo to dryness. The residue was recrystallized from EtOH/hexane to give 9-[5-(3-{4-[bis(2-chloroethyl)amino]phenyl}ureido)-2-methyl-phenylamino]-5-methyl-acridine-4-carboxylic acid (2-dimethylaminoethyl)amide (19, BO-1053); 0.385 g (32%); mp 286-289° C.; 1H NMR (DMSO-d6) δ 2.19 (3H, s, Me), 2.67 (6H, m, NMe2), 2.85 (3H, s, Me), 3.14 (2H, brs, CH2), 3.63-3.69 (8H, m, 4×CH2), 3.85 (2H, brs, CH2), 6.41 (1H, m, ArH,), 6.65 (2H, d, J=9.0 Hz, ArH), 6.97 (1H, m, ArH), 7.24 (2H, d, J=9.0 Hz, ArH), 7.36-7.44 (1H, m, ArH), 7.51 (1H, m, ArH), 7.74 (2H, m, ArH), 7.93 (1H, m, ArH), 8.09 (1H, m, ArH), 8.41 (1H, m, ArH), 8.67 (1H, m, ArH), 9.04 (1H, brs, exchangeable, NH), 9.45 (1H, brs, exchangeable, NH), 12.18 (1H, brs, exchangeable, NH). Anal. Calcld. for (C37H41Cl2N7O2.6H2O): C, 54.91; H, 5.20; N, 12.34. Found: C, 55.08; H, 5.32; N, 12.44.

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered through a pad of Celite
  3. additionthe filtrate containing crude mustard isocyanate 39
  4. customThe solvent removed under reduced pressure to dryness
  5. dissolutionthe residue was dissolved in a mixture of CHCl3/MeOH
  6. additioncontaining silica gel (10 gm)
  7. customevaporated in vacuo to dryness
  8. customchromatographed
  9. additionThe fractions containing the main product
  10. customevaporated in vacuo to dryness
  11. customThe residue was recrystallized from EtOH/hexane

Quellen und Nachweise

ORD-Eintrag
ord-a5d6772116a544a994c92601610fb765
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08222297B2

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