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

HRID 919583Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 919583
[CH2:1]([N:3]([C@H:23]1[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]1)[C:4]1[C:5]2[CH:12]=[CH:11][N:10]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:6]=2[N:7]=[CH:8][N:9]=1)[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:50][C:51]1[CH:52]=[C:53]([NH:58][CH2:59][C:60](O)=[O:61])[CH:54]=[C:55]([Cl:57])[CH:56]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Cl:50][C:51]1[CH:52]=[C:53]([NH:58][CH2:59][C:60]([N:25]2[CH2:26][CH2:27][CH2:28][C@H:23]([N:3]([CH2:1][CH3:2])[C:4]3[C:5]4[CH:12]=[CH:11][N:10]([S:13]([C:16]5[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=5)(=[O:14])=[O:15])[C:6]=4[N:7]=[CH:8][N:9]=3)[CH2:24]2)=[O:61])[CH:54]=[C:55]([Cl:57])[CH:56]=1

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 13138167(3,5-Dichlorophenyl)glycineHCID 118906729(S)-N-ethyl-N-(piperidin-3-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Produkt 1

HCID 86706457(S)-2-(3,5-dichlorophenylamino)-1-(3-(ethyl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)ethanoneAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (S)—N-ethyl-N-(piperidin-3-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (60 mg, 0.15 mmol), in DMF (5 mL), was added EDCI (34 mg, 0.18 mmol), HOBt (24 mg, 0.18 mmol), 2-(3,5-dichlorophenylamino)acetic acid (33 mg, 0.15 mmol) and DIEA (0.06 mL, 0.36 mmol) at 0° C. The reaction mixture was stirred overnight at rt. After completion of the reaction, the reaction mixture was diluted with EtOAc (25 mL) and the organic phase was washed with water (10 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to give the crude compound that was purified by column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford the titled compound (75 mg, 82%). LC-MS: m/z [M+1]=601.

Aufarbeitung

  1. customAfter completion of the reaction
  2. washthe organic phase was washed with water (10 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give the crude compound that
  6. customwas purified by column chromatography (silica gel, gradient MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-3b97322cd3ae419883c11ee7d8844959
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273028B2

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