Sodium Carbonate → HCID 68006956, Verbindung

HRID 526998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 526998
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@H:9]2[CH2:14][CH2:13][CH2:12][C@:11]([CH2:16][NH:17][C:18](=[O:20])[CH3:19])([OH:15])[CH2:10]2)[C:5]([F:21])=[CH:4][N:3]=1.[Cl:22][C:23]1[CH:24]=[C:25]2[C:31](B3OC(C)(C)C(C)(C)O3)=[CH:30][N:29](S(C3C=CC(C)=CC=3)(=O)=O)[C:26]2=[N:27][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.CS(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[ClH:1].[Cl:22][C:23]1[CH:24]=[C:25]2[C:31]([C:2]3[N:7]=[C:6]([NH:8][C@H:9]4[CH2:14][CH2:13][CH2:12][C@:11]([CH2:16][NH:17][C:18](=[O:20])[CH3:19])([OH:15])[CH2:10]4)[C:5]([F:21])=[CH:4][N:3]=3)=[CH:30][NH:29][C:26]2=[N:27][CH:28]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 575977475-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 86667427HCID 86667427, Verbindung2×

Produkt 1

HCID 68006956HCID 68006956, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

N-{[(1S,3S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)-1-hydroxycyclohexyl]-methyl}-acetamide, 46c, (0.2 g, 0.6 mmol) was dissolved in acetonitrile (6 mL) and treated with 5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine (0.5 g, 1.2 mmol) followed by Pd(PPh3)4 (0.07 g, 0.06 mmol). Aqueous 2M sodium carbonate (3.0 mL, 6.1 mmol) was added, and the vial was sealed and heated in the microwave to 130° C. for 30 min. The organic layer was collected and concentrated in vacuo to provide the crude product, which was dissolved in DMSO and purified by HPLC using 5-70% MeOH/H2O with 6 mM HCl over 15 minutes to provide after concentration 75 mg of N-{[(1S,3S)-3-(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-1-hydroxycyclohexyl]methyl}acetamide hydrochloride as an off-white crystalline solid.

Aufarbeitung

  1. customthe vial was sealed
  2. customThe organic layer was collected
  3. concentrationconcentrated in vacuo
  4. customto provide the crude product, which
  5. custompurified by HPLC
  6. customover 15 minutes

Quellen und Nachweise

ORD-Eintrag
ord-01343cdb79894fec9b1708f42a939e56
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345708B2

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