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p-Toluenesulfonic acid → 1-(Chloromethyl)-N-(2-hydroxyethyl)-3-[(E)-4-methoxycinnamoyl]-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-sulfonamide

HRID 2238381
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2238381
[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][C:14]([S:16]([NH:19][CH2:20][CH2:21][OH:22])(=[O:18])=[O:17])=[CH:15][C:9]=3[C:8]([N+:23]([O-:25])=[O:24])=[CH:7][C:6]=2[NH:5][CH2:4]1.[CH3:26][O:27][C:28]1[CH:38]=[CH:37][C:31](/[CH:32]=[CH:33]/[C:34](O)=[O:35])=[CH:30][CH:29]=1.CCN=C=NCCCN(C)C.CC1C=CC(S(O)(=O)=O)=CC=1>CO.Cl.O.CC(N(C)C)=O>[Cl:1][CH2:2][CH:3]1[C:11]2[C:10]3[CH:12]=[CH:13][C:14]([S:16]([NH:19][CH2:20][CH2:21][OH:22])(=[O:17])=[O:18])=[CH:15][C:9]=3[C:8]([N+:23]([O-:25])=[O:24])=[CH:7][C:6]=2[N:5]([C:34](=[O:35])/[CH:33]=[CH:32]/[C:31]2[CH:37]=[CH:38][C:28]([O:27][CH3:26])=[CH:29][CH:30]=2)[CH2:4]1
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Komponenten

8

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 6994144-Methoxycinnamic AcidHCID 686939191-(chloromethyl)-N-(2-hydroxyethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-sulfonamide

Produkt 1

HCID 115195861-(Chloromethyl)-N-(2-hydroxyethyl)-3-[(E)-4-methoxycinnamoyl]-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-sulfonamide
Ausbeute 65,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittelHCID 21893726Hydrochloride methanolLösungsmittel

Versuchsvorschrift

(Scheme C). Amine 121 (75 mg, 0.19 mmol) was dissolved in MeOH/HCl(g) at room temperature and the solution was evaporated to dryness under reduced pressure. (E)-4-methoxycinnamic acid (41 mg, 0.23 mmol), EDCI (149 mg, 0.78 mmol), anhydrous TsOH (30 mg, 0.17 mmol) and dry DMA (3 mL) were then added and the mixture was sired at room temperature for 2 h. The mixture was poured into water and the precipitate was collected, washed with water, dried and dissolved in the minimum volume of DMW at room temperature. The solution was diluted with EtOAc, filtered and then diluted with hexane and refrigerated to give 37 (68 mg, 64%): mp 250-251° C.; 1H NMR [(CD3)2SO)] δ 9.35 (s, 1H), 8.83 (d, J=1.6 Hz, 1H), 8.38 (d, J=8.9 Hz, 1H) 8.00 (dd, J=8.9, 1.7 Hz, 1H), 7.90 (t, J=5.8 Hz, 1H), 7.80 (d, J=8.8 Hz, 2H), 7.74 (d, J=15.3 Hz, 1H), 7.10 (d, J=15.3 z, 1H), 7.03 (d, J=8.81 Hz, 2H), 4.72-4.48 (m, 4 H), 4.13-4.06 (m, 2H), 3.83 (s, 3H), 3.38 (q, J=6.0 Hz, 2H), 2.87 (q, J=6.1 Hz, 2H). Anal. (C25H24ClN3O7S) C, H, N.

Aufarbeitung

  1. customthe solution was evaporated to dryness under reduced pressure
  2. customthe precipitate was collected
  3. washwashed with water
  4. customdried
  5. dissolutiondissolved in the minimum volume of DMW at room temperature
  6. additionThe solution was diluted with EtOAc
  7. filtrationfiltered
  8. additiondiluted with hexane

Quellen und Nachweise

ORD-Eintrag
ord-9c7104afe20d48db8113b17823042fb7
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07718688B2

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