Diisopropylethylamine → 1-(4-Amino-3,5-difluorophenyl)-8-[(3-chloroisonicotinoyl)amino]-4,5-dihydro-1h-benzo[g]indazole-3-carboxamide

https://huagongshe.com/de/reaction/457333

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Diisopropylethylamine	HCID 81531	—
Edukt	3-Chloropyridine-4-carboxylic acid	HCID 2735816	—
Edukt	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Edukt	8-Amino-1-(4-amino-3,5-difluorophenyl)-4,5-dihydro-1h-benzo[g]indazole-3-carboxamide	HCID 22291529	—
Lösungsmittel	Dimethylformamide	HCID 6228	—
Produkt	1-(4-Amino-3,5-difluorophenyl)-8-[(3-chloroisonicotinoyl)amino]-4,5-dihydro-1h-benzo[g]indazole-3-carboxamide	HCID 22291509	15%

Reaktionsschritte

To a mixture of the product from step 3 (0.75 g, 0.0021 mol) and 3-chloroisonicotinic cid (0.33 g, 0.0023 mol) in 20 mL of DMF was added 1 mL of diisopropylethylamine, followed by the addition of HATU (0.9 g, 0.0023 mol). The reaction was stirred at room temperature for 16 h and concentrated. The crude was purified by reverse phase HPLC to give 0.15 g of 1-(4-amino-3,5-difluorophenyl)-8-[(3-chloroisonicotinoyl)amino]-4,5-dihydro-1H-benzo[g]indazole-3-carboxamide as a pale white solid (15% yield); 1HNMR (DMSO, 400 MHz) δ: 10.56 (s, 1H), 8.76 (s, 1H), 8.63 (d, 1H), 8.56 (s, 1H), 7.54 (d, 1H), 7.49 (dd, 1H), 7.35 (m, 2H), 7.31 (s, 1H), 6.71 (m, 2H), 5.88 (s, 2H), 2.92 (m, 4H); Anal. Calcd. for C24H17FClN6O2+0.5H2O: C, 57.21; H, 3.60; N, 16.68. Found: C, 56.91; H, 3.70; N, 16.64.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US07186743B2
Quelldatensatz	uspto-grants-2007_03
ORD ID	ord-51a8e724cb5c4401ae36db3c1ffed2fc
Quellennotiz	uspto-grants-2007_03