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Hydrazine hydrate (1:1) → HCID 66799788, Verbindung

HRID 528048
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 528048
[CH3:1][N:2]1[C:10]([C:11]([OH:13])=O)=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[N:14]1[CH2:19][CH2:18][CH:17]([N:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[NH:22][C:21]2=[O:29])[CH2:16][CH2:15]1.CN(C(O[N:38]1[N:46]=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.O.NN>C(OCC)(=O)C.CN(C)C=O>[CH3:1][N:2]1[C:10]([C:11]([NH:38][NH2:46])=[O:13])=[N:9][C:8]2[C:3]1=[N:4][CH:5]=[N:6][C:7]=2[N:14]1[CH2:15][CH2:16][CH:17]([N:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[NH:22][C:21]2=[O:29])[CH2:18][CH2:19]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 24654Hydrazine hydrate (1:1)HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66799955HCID 66799955, Verbindung

Produkt 1

HCID 66799788HCID 66799788, VerbindungAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a 10 mL round bottomed flask, 9-Methyl-6-[4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl]-9H-purine-8-carboxylic acid (250 mg, 0.68 mmol, 1 equiv) and HATU (390 mg, 1.03 mmol, 1.5 equiv) were suspended anhydrous dimethylformamide (3 mL). Diisopropylethylamine (235 μL, 1.35 mmol, 2 equiv) followed by hydrazine monohydrate (330 μL, 6.81 mmol, 10 equiv) were added and the reaction stirred for one hour. The reaction mixture was diluted with ethyl acetate (20 mL), and the extracted with water (10 mL). The combined aqueous layer was then acidified with 1N aqueous hydrochloric acid to precipitate the desired product. This precipitate was filtered off, washed with water (2 mL) and acetonitrile (1 mL) and air dried yielding 115 mg of 9-methyl-6-(4-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidin-1-yl)-9H-purine-8-carbohydrazide, which was used directly in the next step.

Aufarbeitung

  1. additionwere added
  2. extractionthe extracted with water (10 mL)
  3. customto precipitate the desired product
  4. filtrationThis precipitate was filtered off
  5. washwashed with water (2 mL) and acetonitrile (1 mL) and air
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ea8b9fe2c6ac4449a63496cdbf2465aa
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09346807B2

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