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4-Iodo-2-methoxynicotinaldehyde → 4-[2-(4-Iodo-2-methoxy-pyridin-3-yl)-7-methyl-3H-benzoimidazol-5-yl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1354627
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1354627
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([CH3:20])[C:17]([NH2:21])=[C:16]([NH2:22])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I:23][C:24]1[CH:29]=[CH:28][N:27]=[C:26]([O:30][CH3:31])[C:25]=1[CH:32]=O>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([CH3:20])[C:17]3[N:21]=[C:32]([C:25]4[C:26]([O:30][CH3:31])=[N:27][CH:28]=[CH:29][C:24]=4[I:23])[NH:22][C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 100383814-Iodo-2-methoxynicotinaldehydeHCID 235419144-(3,4-Diamino-5-methyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 235419074-[2-(4-Iodo-2-methoxy-pyridin-3-yl)-7-methyl-3H-benzoimidazol-5-yl]-piperazine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 4-(3,4-Diamino-5-methyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (44.6 mmol—assuming 100% conversion in previous step) in methanol (ca 2700 mL) at 0° C. under a nitrogen atmosphere was slowly added (2 h) via addition funnel, a solution of 4-iodo-2-methoxy-pyridine-3-carbaldehyde (15.0 g, 57.1 mmol) in anhydrous methanol (225 mL). The resulting solution was then stirred at 0° C. for an additional 30 min,. the cooling bath was removed, and the reaction mixture was allowed to stir at room temperature in the presence of air for 72 h. The resulting solution was concentrated in vacuo and the residue was dissolved in dichloromethane (1500 mL) and the solvent removed in vacuo (repeated 3×). The resulting dark foamy solid was dried under high vacuum. 1H NMR (500 MHz, CDCl3) δ 7.82 (d, 1H, J=5.4 Hz), 7.50 (d, 1H, J=5.4 Hz), 6.98 (brs, 1H), 6.90 (brs, 1H), 4.05 (s, 3H), 3.67–3.58 (m, 4H), 3.18–3.09 (m, 4H), 2.63 (s, 3H), 1.49 (s, 9H);. LCMS (M+H)+ m/z 550.

Aufarbeitung

  1. additionvia addition funnel
  2. customthe cooling bath was removed
  3. stirringto stir at room temperature in the presence of air for 72 h
  4. concentrationThe resulting solution was concentrated in vacuo
  5. dissolutionthe residue was dissolved in dichloromethane (1500 mL)
  6. customthe solvent removed in vacuo (repeated 3×)
  7. customThe resulting dark foamy solid was dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-39bc6e5e51b04d39a2a85f674574eaf1
Quelldatensatz
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07223757B2

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