1,2-Dichloroethane → 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide

HRID 1072132

Reaktionsgleichung

Reaktionsgleichung von HRID 1072132
[CH:1]([C:3]1[NH:7][C:6]([C:8]([OH:10])=O)=[CH:5][C:4]=1[CH3:11])=[O:2].[NH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>C(#N)C>[N:15]1([CH2:14][CH2:13][NH:12][C:8]([C:6]2[NH:7][C:3]([CH:1]=[O:2])=[C:4]([CH3:11])[CH:5]=2)=[O:10])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 4082852-MorpholinoethylamineHCID 98988845-formyl-4-methyl-1H-pyrrole-2-carboxylic Acid

Produkt 1

HCID 112770865-formyl-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amideAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a suspension of 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid (2 g, 13 mmol) in acetonitrile was added 4-(2-aminoethyl)morpholine (1.9 mL, 14 mmol), EDC (2.7 g, 14 mmol), HOBt (1.9 g, 14 mmol) and triethylamine (3.6 mL, 26 mmol) sequentially. The reaction mixture was stirred at room temperature for 12 hours and concentrated at reduced pressure. The residue was dissolved in 300 mL of 1N hydrogen chloride solution. The aqueous layer was washed with 150 mL of ethyl acetate twice and basified with sodium bicarbonate. The product was then extracted with 250 mL of dichloromethane twice, dried over MgSO4, and concentrated to afford 1.8 g (53%) of 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid (2-morpholin-4-yl-ethyl)-amide as a yellowish solid. 1H NMR (300 MHz, DMSO-d6) d 12.19 (br s, 1H, NH), 9.72 (s, 1H, CHO), 8.29 (br t, J=6.6 Hz, 1H, CONH), 6.65 (d, J=1.7 Hz, 1H), 3.5 (m, 4H), 3.3 (m, 2H, CONHCH2), 2.4 (m, 6H), 2.28 (s, 3H, CH3). MS m/z 265 [M+].

Aufarbeitung

  1. concentrationconcentrated at reduced pressure
  2. dissolutionThe residue was dissolved in 300 mL of 1N hydrogen chloride solution
  3. washThe aqueous layer was washed with 150 mL of ethyl acetate twice
  4. extractionThe product was then extracted with 250 mL of dichloromethane twice
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d08958097f554527b8490af95a96cb0b
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908930B2

Verknüpfte Notizen

Wird geladen…