1,2-Dichloroethane → 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (4-hydroxymethyl-tetrahydro-pyran-4-yl)-amide

HRID 2191585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2191585
[CH:1]1([C:4]2[N:5]=[C:6]3[C:12]([C:13]([OH:15])=O)=[CH:11][N:10]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1.C(Cl)CCl.[NH2:28][C:29]1([CH2:35][OH:36])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>C(Cl)Cl.CN(C)C1C=CN=CC=1.O>[OH:36][CH2:35][C:29]1([NH:28][C:13]([C:12]2[C:6]3[C:7](=[N:8][CH:9]=[C:4]([CH:1]4[CH2:3][CH2:2]4)[N:5]=3)[N:10]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=2)=[O:15])[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1

Komponenten

7

Edukt 3

HCID 111,2-DichloroethaneHCID 18316484(4-Aminooxan-4-yl)methanolHCID 578296532-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid

Produkt 1

HCID 670020152-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (4-hydroxymethyl-tetrahydro-pyran-4-yl)-amideAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (0.20 g, 0.59 mmol) in CH2Cl2 (5 mL) was added EDC (0.14 g, 0.72 mmol), 4-(dimethylamino)pyridine (0.088 g, 0.72 mmol), and (4-aminotetrahydropyran-4-yl)-methanol (0.094 g, 0.72 mmol). The reaction mixture was stirred at room temperature overnight then diluted with H2O and extracted with CH2Cl2. The combined organics were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by SiO2 chromatography (60% EtOAc/hexanes) to obtain 0.15 g (57%) of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (4-hydroxymethyl-tetrahydro-pyran-4-yl)-amide as an oil.

Aufarbeitung

  1. extractionextracted with CH2Cl2
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by SiO2 chromatography (60% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ebb5c94234ba4b2aa08442fe6767d172
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329699B2

Notizen zur Reaktion

Wird geladen…