Diisopropylethylamine → Methyl 1-{[(3-chloro-2'-{4-chloro-3-[3-(dimethylamino)propoxy]-phenyl}-5-methyl-2,3'-bipyridin-6'-yl)carbonyl]amino}cyclohexane-carboxylate hydrochloride

HRID 244069

Reaktionsgleichung

Reaktionsgleichung von HRID 244069
[Cl:1][C:2]1[C:3]([C:9]2[C:10]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([O:25][CH2:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])[CH:19]=3)=[N:11][C:12]([C:15](O)=[O:16])=[CH:13][CH:14]=2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.CCN(C(C)C)C(C)C.Cl.[NH2:42][C:43]1([C:49]([O:51][CH3:52])=[O:50])[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(#N)C>[ClH:1].[Cl:1][C:2]1[C:3]([C:9]2[C:10]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([O:25][CH2:26][CH2:27][CH2:28][N:29]([CH3:30])[CH3:31])[CH:19]=3)=[N:11][C:12]([C:15]([NH:42][C:43]3([C:49]([O:51][CH3:52])=[O:50])[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]3)=[O:16])=[CH:13][CH:14]=2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22645079Methyl 1-aminocyclohexane-1-carboxylate hydrochlorideHCID 66840942HCID 66840942, Verbindung

Produkt 1

HCID 66840590Methyl 1-{[(3-chloro-2'-{4-chloro-3-[3-(dimethylamino)propoxy]-phenyl}-5-methyl-2,3'-bipyridin-6'-yl)carbonyl]amino}cyclohexane-carboxylate hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 134 mg (0.29 mmol) of 3-chloro-2′-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-methyl-2,3′-bipyridine-6′-carboxylic acid in 5 mL of anhydrous acetonitrile are successively added 0.18 mL (1.02 mmol) of DIEA and 56 mg (0.29 mmol) of methyl 1-aminocyclohexanecarboxylate hydrochloride. The mixture is cooled to 0° C. and 112 mg (0.35 mmol) of TBTU are added. After stirring for 18 hours between 0 and 10° C., the reaction medium is concentrated under reduced pressure and then taken up in 20 mL of a 1/1 EtOAc/ether mixture. After washing with 10 mL of water and 10 mL of saturated aqueous NaHCO3 solution, the organic phase is dried over Na2SO4 and concentrated under reduced pressure. 0.2 mL (0.1 mmol) of a 2N solution of HCl in ether and then 20 mL of anhydrous ether are added to the residue, taken up in 5 mL of DCM, which allows precipitation of 139 mg of methyl 1-{[(3-chloro-2′-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-methyl-2,3′-bipyridin-6′-yl)-carbonyl]amino}cyclohexanecarboxylate hydrochloride in the form of a white powder.

Aufarbeitung

  1. concentrationthe reaction medium is concentrated under reduced pressure
  2. washAfter washing with 10 mL of water and 10 mL of saturated aqueous NaHCO3 solution
  3. dry with materialthe organic phase is dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. addition0.2 mL (0.1 mmol) of a 2N solution of HCl in ether and then 20 mL of anhydrous ether are added to the residue
  6. customprecipitation of 139 mg of methyl 1-{[(3-chloro-2′-{4-chloro-3-[3-(dimethylamino)propoxy]phenyl}-5-methyl-2,3′-bipyridin-6′-yl)-carbonyl]amino}cyclohexanecarboxylate hydrochloride in the form of a white powder

Quellen und Nachweise

ORD-Eintrag
ord-82e6e57a8dcb47a1aa1e5a73e29b4e15
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653276B2

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