4-Methylmorpholine → 2-(3,4-Dichloro-phenylamino)-N-(2,2-dimethoxy-ethyl)-N-(3-piperidin-1-yl-propyl)-propionamide

HRID 1096272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096272
[CH3:1][O:2][CH:3]([O:15][CH3:16])[CH2:4][NH:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[Cl:17][C:18]1[CH:19]=[C:20]([NH:25][CH:26]([CH3:30])[C:27](O)=[O:28])[CH:21]=[CH:22][C:23]=1[Cl:24].CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[Cl:17][C:18]1[CH:19]=[C:20]([NH:25][CH:26]([CH3:30])[C:27]([N:5]([CH2:4][CH:3]([O:15][CH3:16])[O:2][CH3:1])[CH2:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:28])[CH:21]=[CH:22][C:23]=1[Cl:24]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 69164262-(3,4-Dichloro-phenylamino)-propionic Acid2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 63685354(2,2-Dimethoxy-ethyl)-(3-piperidin-1-yl-propyl)-amine

Produkt 1

HCID 667831682-(3,4-Dichloro-phenylamino)-N-(2,2-dimethoxy-ethyl)-N-(3-piperidin-1-yl-propyl)-propionamideAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (2,2-dimethoxy-ethyl)-(3-piperidin-1-yl-propyl)-amine (400 mg, 1.74 mmol) in N,N-dimethylformamide (4 mL) were added 2-(3,4-dichloro-phenylamino)-propionic acid (intermediate 11; 337 mg, 1.91 mmol), 4-methylmorpholine (527 mg, 5.21 mmol) and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (990 mg, 2.61 mmol) at RT, then after 2 h the reaction mixture was partitioned between EtOAc and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2; CH2Cl2/MeOH/25% aq. ammonia solution 90:10:0.25) afforded the title compound (545 mg, 70%). Yellow viscous oil, MS: 446.2 (M+H)+.

Aufarbeitung

  1. customafter 2 h the reaction mixture was partitioned between EtOAc and sat. aq. NaHCO3 solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d15508d7413f4fa68afba8c1a71b8519
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138175B2

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