Sodium Bicarbonate → HCID 58026471, Verbindung

HRID 1367922Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1367922
[C:1]1([C:7]#[C:8][C:9]2[N:14]=[C:13]([C:15]([OH:17])=O)[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.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:8]#[C:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=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 669404046-Phenylethynyl-pyridine-2-carboxylic acidHCID 178508178HCID 178508178, Verbindung2×

Produkt 1

HCID 58026471HCID 58026471, VerbindungAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

0.05 (0.23 mmol) of the above synthesized 6-Phenylethynyl-pyridine-2-carboxylic acid, 0.095 g (0.25 mmol) of HBTU in a mixture of 2.0 ml of DMF and 0.20 mL of DIEA was reacted with 0.05 g (0.20 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. 5.0 mL of water and 5.0 mL of saturated NaHCO3 was added, and the resulting solid was filtered. The solid was washed with water and ether and dried to provide 0.04 g (43%) of 2-[(6-phenylethynyl-pyridine-2-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide. 1H-NMR (400 MHz, DMSO): 8.3 (d, 1H), 8.21 (t, 1H), 8.12 (bs, 1H), 8.02 (d, 1H), 7.94 (d, 1H), 7.72 (m, 2H), 7.50 (m, 4H), 7.40 (s, 2H) ppm; LCMS: 448 (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-239e517cd5da46c4a017389c74628427
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893267B2

Notizen zur Reaktion

Wird geladen…