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Dimethylformamide → 10-{[2'-(Cyanomethyl)-1,1'-biphenyl-4-yl]carbonyl}-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

HRID 2244222
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2244222
S(Cl)(Cl)=O.[C:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=O)=[CH:16][CH:15]=1)#[N:6].[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][NH:30][C:31]([C:33]2[N:42]3[C:36]([CH2:37][NH:38][C:39]4[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=4[CH2:41]3)=[CH:35][CH:34]=2)=[O:32])[CH:24]=1.CN(C)C=O>O1CCOCC1>[C:5]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([C:20]([N:38]2[C:39]3[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=3[CH2:41][N:42]3[C:33]([C:31]([NH:30][CH2:29][C:25]4[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=4)=[O:32])=[CH:34][CH:35]=[C:36]3[CH2:37]2)=[O:22])=[CH:18][CH:19]=1)#[N:6]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22053658N-(3-Pyridinylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamideHCID 686894952'-(Cyanomethyl)-1,1'-biphenyl-4-carboxylic acid

Produkt 1

HCID 1595170510-{[2'-(Cyanomethyl)-1,1'-biphenyl-4-yl]carbonyl}-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 20 mL of thionyl chloride and 0.243 g (0.001 mol) of 2′-(cyanomethyl)-1,1′-biphenyl-4-carboxylic acid of Step A was heated under reflux for 1 hour. The excess thionyl chloride was removed in vacuo. To the residue was added 35 mL of dry 1,4-dioxane, 0.318 g (0.001 mol) of N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide and 0.122 g (0.001 mol) of N,N-dimethylformamide. The reaction was heated under reflux for three hours, cooled and evaporated to dryness. The residue was collected, washed with water and triturated with ether to give 0.62 g. of a tan solid, m.p. 105-108° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. customThe excess thionyl chloride was removed in vacuo
  4. temperatureThe reaction was heated
  5. temperatureunder reflux for three hours
  6. temperaturecooled
  7. customevaporated to dryness
  8. customThe residue was collected
  9. washwashed with water
  10. customtriturated with ether
  11. customto give 0.62 g

Quellen und Nachweise

ORD-Eintrag
ord-ea36873d3d2746f9b0f397cf0441c0dd
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07678787B2

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