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Triethylamine → methyl 4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzoate

HRID 44223
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 44223
CS[C:3]1[C:4]2[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=2[NH:6][C:7]2[N:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1.[NH:18]([C:20]([C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1)=O)[NH2:19].C(N(CC)CC)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl.CO>[N:19]1[N:18]=[C:20]([C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=2)[N:9]2[C:3]=1[C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[NH:6][C:7]1[N:13]=[CH:12][CH:11]=[CH:10][C:8]2=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 596004Methyl 4-(hydrazinecarbonyl)benzoateHCID 1682401610-(Methylsulfanyl)-2,4,9-triazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,9,12,14-heptaene

Produkt 1

HCID 136163852methyl 4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzoate
Ausbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 6-(methylthio)-11H-benzo[e]pyrido[3,2-b][1,4]diazepine (2.5 g, 10.4 mmol) in dichloromethane (50 mL) and methanol (20 mL) was added the methyl 4-(hydrazinecarbonyl)benzoate (4.02 g, 20.7 mmol) followed by triethyl amine (1 mL) and p-toluenesulfonic acid monohydrate (3.3 g, 17.3 mmol). The reaction mixture was stirred at 70° C. for 20 hours. The mixture was partitioned between water (100 mL) and dichloromethane (150 mL). The phases were separated and the organic phase was washed with water (50 mL) and brine (50 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was triturated from ethyl acetate, the solid filtered off and dried undet vacuum, yielding the methyl 4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzoate as a yellow solid (1.7 g, 44%). M.p.>300° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.83 (s, 1H), 8.23 (dd, J=4.8, 1.6 Hz, 1H), 8.02 (dt, J=8.8, 1.8 Hz, 2H), 7.97 (dd, J=8.0, 1.6 Hz, 1H), 7.58 (dt, J=8.8, 1.8 Hz, 2H), 7.45 (td, J=5.1, 1.6 Hz, 1H), 7.35 (d, J=7.2 Hz, 1H), 7.2-7.1 (m, 2H), 6.91 (dd, J=8.4, 4.8 Hz, 1H), 3.88 (s, 3H); LCMS [M+H]: 370.

Aufarbeitung

  1. customThe mixture was partitioned between water (100 mL) and dichloromethane (150 mL)
  2. customThe phases were separated
  3. washthe organic phase was washed with water (50 mL) and brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated from ethyl acetate
  8. filtrationthe solid filtered off
  9. customdried undet vacuum

Quellen und Nachweise

ORD-Eintrag
ord-79e9a5fb9d124b6f8924805938853b05
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08541407B2

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