3-Aminopyridine → 2-(6-chloro-1-methyl-1H-indazol-3-yl)-N-(pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246621

Reaktionsgleichung

Reaktionsgleichung von HRID 246621
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21]([OH:23])=O)=[CH:19][NH:18][C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C1C=CN=CC=1)C.CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21]([NH:30][C:26]5[CH:25]=[N:24][CH:29]=[CH:28][CH:27]=5)=[O:23])=[CH:19][NH:18][C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1

Komponenten

8

Edukt 5

HCID 100093-AminopyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 712800962-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Produkt 1

HCID 712796922-(6-chloro-1-methyl-1H-indazol-3-yl)-N-(pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.07 g, 0.3 mmol), pyridin-3-amine (0.05 g, 0.53 mmol), EDCI (0.057 g, 0.3 mmol), DMAP (0.037 g, 0.3 mmol), and DIPEA (0.163 g, 1.26 mmol) in 10 mL of DMF were stirred at room temperature for 5 hours. Then HATU (0.114 g, 0.3 mmol) was added, the final reaction mixture was stirred for additional. The solvent was removed under reduced pressure at 70° C. The residue was triturated with water, EtOAc and DMSO successively then decanted and dried to give 2-(6-chloro-1-methyl-1H-indazol-3-yl)-N-(pyridin-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.022 g, 26%) as a white solid. MS: (M+H)+=404; 1H NMR (300 MHz, DMSO): δ 10.20 (s, 1H), 9.09 (s, 1H), 8.90 (s, 1H), 8.63 (s, 1H), 8.54 (d, 1H, J=8.7 Hz), 8.34 (d, 1H, J=4.5 Hz), 8.26 (d, 1H, J=8.7 Hz), 7.98 (s, 1H), 7.47 (dd, 1H, J=8.4, 4.8 Hz), 7.22 (d, 1H, J=8.4 Hz), 4.17 (s, 3H).

Aufarbeitung

  1. customthe final reaction mixture
  2. stirringwas stirred for additional
  3. customThe solvent was removed under reduced pressure at 70° C
  4. customThe residue was triturated with water, EtOAc and DMSO successively
  5. customdecanted
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8c16b8cd204f49039518315217b668c6
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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