Dichloromethane → (E)-3-(4-Ethoxycarbonylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochloride

HRID 1711836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1711836
C([O:5][C:6](=[O:27])/[CH:7]=[CH:8]/[C:9]1[CH:26]=[N:25][C:12]2[NH:13][C:14](=[O:24])[CH2:15][N:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][C:11]=2[CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:36]>>[ClH:36].[CH2:22]([O:21][C:19]([CH2:18][N:16]1[CH2:17][C:11]2[CH:10]=[C:9](/[CH:8]=[CH:7]/[C:6]([OH:27])=[O:5])[CH:26]=[N:25][C:12]=2[NH:13][C:14](=[O:24])[CH2:15]1)=[O:20])[CH3:23]

Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59456982(E)-3-(4-Ethoxycarbonylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid tert-butyl ester

Produkt 1

HCID 66966559(E)-3-(4-Ethoxycarbonylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochlorideAusbeute 88 %

Versuchsvorschrift

A solution of (E)-3-(4-ethoxycarbonylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid tert-butyl ester (1.14 g, 3.04 mmol) in CH2Cl2 (8 mL) was treated with TFA (8 mL). After stirring at room temperature under N2 for 45 min, the clear tan solution was concentrated in vacuo. The resulting oil was treated with anhydrous HCl in dioxane (10 mL, 4.0 M) and sonicated until the oil was converted to a fine off-white solid. The resulting mixture was diluted with Et2O (100 mL) and stirred under N2 for 20 min. The solid was isolated by filtration, washed with Et2O, and dried under vacuum at 50° C. overnight to give the title compound (1.05 g, 88%) as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 10.57 (s, 1H), 8.56-8.55 (m, 1H), 8.10 (s, 1H), 6.57 (d, J=16.0 Hz, 1H), 6.57 (d, J=16.0 Hz, 1H), 4.14-4.05 (m, 3H), 3.62-3.56 (m, 6H), 1.18 (t, J=7.1 Hz, 3H); MS (EST) m/e 320 (M+H)+.

Aufarbeitung

  1. concentrationthe clear tan solution was concentrated in vacuo
  2. additionThe resulting oil was treated with anhydrous HCl in dioxane (10 mL, 4.0 M)
  3. customsonicated until the oil
  4. additionThe resulting mixture was diluted with Et2O (100 mL)
  5. stirringstirred under N2 for 20 min
  6. customThe solid was isolated by filtration
  7. washwashed with Et2O
  8. customdried under vacuum at 50° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-05449d29eba0414c8326131608ae5bca
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790709B2

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