1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (R)-2-(3,5-dichlorophenylamino)-1-(3-((2-hydroxyethyl)(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)ethanone

HRID 919574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 919574
[NH:1]1[CH2:6][CH2:5][CH2:4][C@@H:3]([N:7]([C:11]2[C:12]3[CH:19]=[CH:18][N:17]([S:20]([C:23]4[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=4)(=[O:22])=[O:21])[C:13]=3[N:14]=[CH:15][N:16]=2)[CH2:8][CH2:9][OH:10])[CH2:2]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:51][C:52]1[CH:53]=[C:54]([NH:59][CH2:60][C:61](O)=[O:62])[CH:55]=[C:56]([Cl:58])[CH:57]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Cl:51][C:52]1[CH:53]=[C:54]([NH:59][CH2:60][C:61]([N:1]2[CH2:6][CH2:5][CH2:4][C@@H:3]([N:7]([CH2:8][CH2:9][OH:10])[C:11]3[C:12]4[CH:19]=[CH:18][N:17]([S:20]([C:23]5[CH:24]=[CH:25][C:26]([CH3:27])=[CH:28][CH:29]=5)(=[O:21])=[O:22])[C:13]=4[N:14]=[CH:15][N:16]=3)[CH2:2]2)=[O:62])[CH:55]=[C:56]([Cl:58])[CH:57]=1

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13138167(3,5-Dichlorophenyl)glycineHCID 69676526(R)-2-(piperidin-3-yl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethanol

Produkt 1

HCID 69676522(R)-2-(3,5-dichlorophenylamino)-1-(3-((2-hydroxyethyl)(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)ethanoneAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (R)-2-(piperidin-3-yl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethanol (0.9 mg, 2.2 mmol) in DMF (10 mL) was added EDCI (494 mg, 2.6 mmol), HOBt (351 mg, 2.6 mmol), 2-(3,5-dichlorophenylamino)acetic acid (475 mg, 2.16 mmol) and DIEA (0.574 ml, 3.24 mmol) at 0° C. The solution was stirred at rt over night, diluted with EtOAc (25 mL) and washed with water. The aqueous layer was extracted with EtOAc, dried (Na2SO4) and concentrated in vacuo to give a residue which was purified by column chromatography (silica gel, gradient 0-2% methanol in chloroform) to afford the titled compound (0.4 g, 30%). LCMS [M+1]: 617.

Aufarbeitung

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give a residue which
  6. customwas purified by column chromatography (silica gel, gradient 0-2% methanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-8599a715adf34f1d9f8b3b3870e6933a
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273028B2

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