Trifluoroacetic acid → 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (4-hydroxymethyl-tetrahydro-pyran-4-yl)-amide

HRID 2191586Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2191586
[OH:1][CH2:2][C:3]1([NH:9][C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([CH:21]4[CH2:23][CH2:22]4)[N:19]=3)[N:14](COCC[Si](C)(C)C)[CH:13]=2)=[O:11])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.FC(F)(F)C(O)=O>C(Cl)Cl>[OH:1][CH2:2][C:3]1([NH:9][C:10]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([CH:21]4[CH2:23][CH2:22]4)[N:19]=3)[NH:14][CH:13]=2)=[O:11])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 670020152-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (4-hydroxymethyl-tetrahydro-pyran-4-yl)-amide

Produkt 1

HCID 547553722-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (4-hydroxymethyl-tetrahydro-pyran-4-yl)-amideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (4-hydroxymethyl-tetrahydro-pyran-4-yl)-amide (0.15 g, 0.33 mmol) in CH2Cl2 (7.5 mL) was added trifluoroacetic acid (1.5 mL). The reaction mixture was stirred at room temperature overnight then concentrated. The residue was dissolved in MeOH (10 mL) and H2O (1 mL) and Et3N (2 mL) were added. The reaction mixture was stirred at room temperature overnight then concentrated. The residue was triturated with Et2O to afford 96 mg (92%) of 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (4-hydroxymethyl-tetrahydro-pyran-4-yl)-amide as an off-white solid. MS: (M+H)+=317; mp=294.0-296.0.

Aufarbeitung

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in MeOH (10 mL)
  3. additionH2O (1 mL) and Et3N (2 mL) were added
  4. stirringThe reaction mixture was stirred at room temperature overnight
  5. concentrationthen concentrated
  6. customThe residue was triturated with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-9dd3bca75fee40bd9657c03eb7ef8c10
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329699B2

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