Sodium Bicarbonate → 2-{[6-(3-cyano-phenyl)-pyridine-2-carbonyl]-amino}-1H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide

HRID 1845021

Reaktionsgleichung

Reaktionsgleichung von HRID 1845021
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[C:13]([C:15]([OH:17])=O)[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:42]1[CH:46]=[CH:45][N:44]=[C:43]1[NH:47][C:48]([C:50]1[C:58]2[NH:57][C:56]([NH2:59])=[N:55][C:54]=2[CH:53]=[CH:52][CH:51]=1)=[O:49].C([O-])(O)=O.[Na+]>CN(C=O)C.CCN(C(C)C)C(C)C.O>[NH:44]1[CH:45]=[CH:46][N:42]=[C:43]1[NH:47][C:48]([C:50]1[C:58]2[N:57]=[C:56]([NH:59][C:15]([C:13]3[CH:12]=[CH:11][CH:10]=[C:9]([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=4)[N:14]=3)=[O:17])[NH:55][C:54]=2[CH:53]=[CH:52][CH:51]=1)=[O:49]

Komponenten

8

Edukt 4

HCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 24730129HCID 24730129, VerbindungHCID 178508178HCID 178508178, Verbindung2×

Produkt 1

HCID 669404392-{[6-(3-cyano-phenyl)-pyridine-2-carbonyl]-amino}-1H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amideAusbeute 21,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

0.12 g (0.51 mmol) of 6-(3-cyano-phenyl)-pyridine-2-carboxylic acid, 0.19 g (0.5 mmol) of HBTU in a mixture of 2.0 ml of DMF and 0.26 mL of DIEA was reacted with 0.1 g (0.41 mmol) of 2-amino-3H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide (Intermediate B) as described in general procedure A. The reaction mixture was cooled to r.t. and 5.0 mL of water and 5.0 mL of saturated NaHCO3 was added. The resulting solid was filtered, and the solid was washed with water and ether and dried to provide 0.04 g (17.5%) of 2-{[6-(3-cyano-phenyl)-pyridine-2-carbonyl]-amino}-1H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide. 1H-NMR (400 MHz, DMSO): 9.15 (s, 1H), 8.86 (s, 1H), 8.45(m, 1H), 8.24 (m, 2H), 7.99 (d, 1H), 7.92 (d, 1H), 7.87 (d, 1H), 7.72 (t, 1H), 7.41(t, 1H), 7.30 (s, 2H) ppm. LCMS: 449 (M+1)+.

Aufarbeitung

  1. filtrationThe resulting solid was filtered
  2. washthe solid was washed with water and ether
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c08fd1e03ca94c808f82f2834caf207e
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946259B2

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