1,2-Dichloroethane → 1-[4-(Pyrimidin-2-ylaminomethyl)-piperidin-1-yl]4-thiophen-2-yl-butan-1-one

HRID 1351575

Reaktionsgleichung

Reaktionsgleichung von HRID 1351575
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17]CC2C=CC=CC=2)=O)[CH2:11][CH2:10]1.N1CCCCC1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[S:45]1[CH:49]=[CH:48][CH:47]=[C:46]1[CH2:50][CH2:51][CH2:52]C(O)=O>CN(C=O)C>[N:3]1[CH:4]=[CH:5][CH:6]=[N:1][C:2]=1[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15](=[O:17])[CH2:52][CH2:51][CH2:50][C:46]2[S:45][CH:49]=[CH:48][CH:47]=2)[CH2:13][CH2:14]1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 8082PiperidineHCID 757711-HydroxybenzotriazoleHCID 783864-(2-Thienyl)Butyric AcidHCID 9923385Benzyl 4-[(2-pyrimidinylamino)methyl]-1-piperidinecarboxylate

Produkt 1

HCID 221356711-[4-(Pyrimidin-2-ylaminomethyl)-piperidin-1-yl]4-thiophen-2-yl-butan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Benzyl 4-[(2-pyrimidinylamino)methyl]-1-piperidinecarboxylate (EXAMPLE 16) was hydrogenated as described in EXAMPLE 30, Step 1. The resulting piperidine was combined with EDC (1.3 equiv.), HOBT (1.0 equiv.), and 4-thiophen-2-yl-butyric acid (1.0 equiv.) in DMF and stirred for 2 h. The resulting reaction solution was partitioned into ethyl acetate and aqueous sodium bicarbonate. The organic layer was separated and washed with pH 4.5 citric acid buffer (10% citric acid and sodium hydroxide), dried (sodium sulfate), and concentrated to yield the desired 1-[4-(pyrimidin-2-ylaminomethyl)-piperidin-1-yl]4-thiophen-2-yl-butan-1-one. M.S. (M+1): 345.25

Aufarbeitung

  1. customThe resulting reaction solution
  2. customwas partitioned into ethyl acetate and aqueous sodium bicarbonate
  3. customThe organic layer was separated
  4. washwashed with pH 4.5 citric acid buffer (10% citric acid and sodium hydroxide)
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5b82b136b4e042d3bcae1409e7f09efc
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217716B2

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