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Triethylamine → Ethyl 3-[1-(2-{3-Methoxy-4-[(2-toluidinocarbonyl)amino]phenyl}acetyl)-1,2,3,4-tetrahydro-6-quinolinyl]propanoate

HRID 396714
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 396714
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([OH:23])=O)[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11].[NH:24]1[C:33]2[C:28](=[CH:29][C:30]([CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:31][CH:32]=2)[CH2:27][CH2:26][CH2:25]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>O1CCCC1.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([N:24]2[C:33]3[C:28](=[CH:29][C:30]([CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:31][CH:32]=3)[CH2:27][CH2:26][CH2:25]2)=[O:23])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[C:14]([CH3:19])=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:11]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 23003903Ethyl 3-(1,2,3,4-tetrahydro-6-quinolinyl)propanoate

Produkt 1

HCID 23003938
Ethyl 3-[1-(2-{3-Methoxy-4-[(2-toluidinocarbonyl)amino]phenyl}acetyl)-1,2,3,4-tetrahydro-6-quinolinyl]propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A stirred solution of 3-methoxy-4-[3-(2-methylphenyl)ureido]phenylacetic acid (0.232 g, prepared as described in Example 52B of International Patent Application Publication No. WO 96/22966) in anhydrous tetrahydrofuran (5 ml), under an atmosphere of argon and at 20° C., was treated with powdered molecular sieves 4 Å (2 g), ethyl 3-(1,2,3,4-tetrahydro-6-quinolinyl)propanoate (0.115 g, Reference Example 2), triethylamine (0.275 ml), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.223 g) and 4-dimethylaminopyridine (6 mg). After stirring at 20° C. for 1 hour the reaction mixture was filtered through a pad of celite. The filtrate was evaporated under reduced pressure (2.7 kPa) at 40° C. and the residue was treated with ethyl acetate (25 ml). The solution obtained was washed twice with saturated aqueous ammonium chloride solution (5 ml), then with water (5 ml), then dried over magnesium sulfate, and then evaporated under reduced pressure (2.7 kPa) at 40° C. The resulting white foamy solid (0.457 g) was subjected to flash chromatography on silica (0,040-0,063 mm) eluting with a mixture of cyclohexane and ethyl acetate (250 ml, 9:1, then 500 ml, 7:3, then 1000 ml, 4:6; v/v) to give the title compound (0.244 g) as a white foamy solid.

Aufarbeitung

  1. filtrationwas filtered through a pad of celite
  2. customThe filtrate was evaporated under reduced pressure (2.7 kPa) at 40° C.
  3. additionthe residue was treated with ethyl acetate (25 ml)
  4. customThe solution obtained
  5. washwas washed twice with saturated aqueous ammonium chloride solution (5 ml)
  6. dry with materialwith water (5 ml), then dried over magnesium sulfate
  7. customevaporated under reduced pressure (2.7 kPa) at 40° C
  8. washeluting with a mixture of cyclohexane and ethyl acetate (250 ml, 9:1

Quellen und Nachweise

ORD-Eintrag
ord-ce17e4befebd4ae7b33857e5758f7165
Quelldatensatz
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06608084B1

Notizen zur Reaktion

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