Water → N-(1-cyanocyclopropyl)-2-(1,6-dimethyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

HRID 246671Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246671
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:11])[CH:9]=2)[C:4]([C:12]2[N:17]=[C:16]3[C:18]([C:21](O)=[O:22])=[CH:19][NH:20][C:15]3=[N:14][CH:13]=2)=[N:3]1.Cl.[NH2:25][C:26]1([C:29]#[N:30])[CH2:28][CH2:27]1.CCN=C=NCCCN(C)C.O>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:29]([C:26]1([NH:25][C:21]([C:18]2[C:16]3=[N:17][C:12]([C:4]4[C:5]5[C:10](=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=5)[N:2]([CH3:1])[N:3]=4)=[CH:13][N:14]=[C:15]3[NH:20][CH:19]=2)=[O:22])[CH2:28][CH2:27]1)#[N:30]

Komponenten

7

Edukt 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 145863631-Amino-1-cyclopropanecarbonitrile hydrochlorideHCID 712798782-(1,6-dimethyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid

Produkt 1

HCID 71279810N-(1-cyanocyclopropyl)-2-(1,6-dimethyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamideAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred mixture of 2-(1,6-dimethyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (80 mg, 0.26 mmol) and 1-aminocyclopropanecarbonitrile hydrochloride (46 mg, 0.39 mmol) in DMF (3 mL) was added EDCI (100 mg, 0.52 mmol) followed by DMAP (63 mg, 0.52 mmol). The mixture was stirred at room temperature for 16 hours. Then the mixture was poured into water (5 mL) and filtered, the solid was washed with DMSO and MeOH then dried to give N-(1-cyanocyclopropyl)-2-(1,6-dimethyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (22 mg, 23%) as a white solid. MS: (M+H)+=372; 1H NMR (300 MHz, DMSO): δ 12.98 (s, 1H), 9.14 (s, 1H), 8.95 (s, 1H), 8.55 (s, 1H), 7.58 (s, 1H), 7.25 (d, 1H, J=8.4 Hz), 4.17 (s, 3H), 2.56 (s, 3H), 1.77 (d, 2H, J=6.0 Hz), 1.48-1.44 (m, 2H).

Aufarbeitung

  1. filtrationfiltered
  2. washthe solid was washed with DMSO and MeOH
  3. customthen dried

Quellen und Nachweise

ORD-Eintrag
ord-27add4af0890419c97833b505fee14cc
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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