Ethylenediamine → 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-oxazol-4-yl-ethyl)-amide

HRID 245902

Reaktionsgleichung

Reaktionsgleichung von HRID 245902
[O:1]1[CH:5]=[C:4]([CH:6]([NH:8][C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[C:28]5[C:23](=[CH:24][C:25]([F:29])=[CH:26][CH:27]=5)[N:22]([CH3:30])[N:21]=4)[N:18]=3)[N:13](COCC[Si](C)(C)C)[CH:12]=2)=[O:10])[CH3:7])[N:3]=[CH:2]1.FC(F)(F)C(O)=O.C(N)CN>ClCCl>[O:1]1[CH:5]=[C:4]([CH:6]([NH:8][C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([C:20]4[C:28]5[C:23](=[CH:24][C:25]([F:29])=[CH:26][CH:27]=5)[N:22]([CH3:30])[N:21]=4)[N:18]=3)[NH:13][CH:12]=2)=[O:10])[CH3:7])[N:3]=[CH:2]1

Komponenten

5

Edukt 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 712859922-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-oxazol-4-yl-ethyl)-amide

Produkt 1

HCID 712856492-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-oxazol-4-yl-ethyl)-amideAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a round-bottomed flask, 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-oxazol-4-yl-ethyl)-amide (110 mg, 0.205 mmol) was dissolved in dichloromethane (1 ml) and trifluoroacetic acid (0.63 ml, 8.2 mmol) was added. The reaction mixture was stirred at room temperature for 2 h then concentrated. The residue was dissolved in dichloromethane (1 ml) and ethylenediamine (0.83 ml, 12.3 mmol) was added. The yellow solution was stirred at room temperature for 1 h then quenched with water and diluted with ethyl acetate. The resulting suspension was filtered, washed with hot water and ethyl acetate and dried under high vacuum to provide 58 mg (70%) of 2-(6-fluoro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-oxazol-4-yl-ethyl)-amide as a light yellow powder. MS: (M+H)+=406; 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 12.83 (br. s., 1H), 9.12 (s, 1H), 8.42-8.51 (m, 2H), 8.32-8.42 (m, 2H), 8.20 (s, 1H), 7.68 (dd, J=9.8, 1.9 Hz, 1H), 7.04 (td, J=9.3, 1.9 Hz, 1H), 5.28-5.46 (m, 1H), 4.14 (s, 3H), 1.58 (d, J=6.8 Hz, 3H).

Aufarbeitung

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in dichloromethane (1 ml)
  3. stirringThe yellow solution was stirred at room temperature for 1 h
  4. customthen quenched with water
  5. additiondiluted with ethyl acetate
  6. filtrationThe resulting suspension was filtered
  7. washwashed with hot water and ethyl acetate
  8. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-109c0fa4e47f482e800bfaebd17cabfe
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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