5-Amino-1-methyl-1H-pyrazole-4-carbonitrile → 4-amino-5-(1H-benzo[d]imidazol-2-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one

HRID 353804

Reaktionsgleichung

Reaktionsgleichung von HRID 353804
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]#[N:9].[NH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[CH2:19][C:20](OCC)=[O:21].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[NH2:9][C:8]1[C:3]2[CH:4]=[N:5][N:6]([CH3:7])[C:2]=2[NH:1][C:20](=[O:21])[C:19]=1[C:11]1[NH:10][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=1

Komponenten

5

Edukt 3

HCID 2197405-Amino-1-methyl-1H-pyrazole-4-carbonitrileHCID 308071ethyl 2-(1H-1,3-benzodiazol-2-yl)acetateHCID 2733832Lithium Hexamethyldisilazide

Produkt 1

HCID 1354961414-amino-5-(1H-benzo[d]imidazol-2-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-Amino-1-methyl-1H-pyrazole-4-carbonitrile (1.0 eq) and ethyl 1H-benzimidazol-2-ylacetate (1.0 eq) were dissolved in THF and dried over sieves. LiHMDS (3 eq) was added dropwise and the mixture stirred for 18 hours. The mixture was filtered and diluted with EtOAc, then washed with an aqueous saturated NH4Cl solution. The aqueous layer was washed with EtOAc (3×), and the organic layers combined, dried over MgSO4, and concentrated yielding pure product. LC/MS m/z 281.0 (MH+), Rt 1.41 minutes.

Aufarbeitung

  1. customdried over sieves
  2. filtrationThe mixture was filtered
  3. additiondiluted with EtOAc
  4. washwashed with an aqueous saturated NH4Cl solution
  5. washThe aqueous layer was washed with EtOAc (3×)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customyielding pure product

Quellen und Nachweise

ORD-Eintrag
ord-1c679456dc4d4e8aaad9c958ecf5ab34
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756383B2

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