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5-Bromopyrimidine → HCID 16069044, Verbindung

HRID 2047569
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2047569
[N:1]1([C@@H:7]2[CH2:10][C@H:9]([C:11]3[S:12][C:13]4[CH:19]=[C:18]([NH2:20])[CH:17]=[CH:16][C:14]=4[N:15]=3)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:22]1[CH:23]=[N:24][CH:25]=[N:26][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[N:1]1([CH:7]2[CH2:10][CH:9]([C:11]3[S:12][C:13]4[CH:19]=[C:18]([NH:20][C:22]5[CH:23]=[N:24][CH:25]=[N:26][CH:27]=5)[CH:17]=[CH:16][C:14]=4[N:15]=3)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 783445-BromopyrimidineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 178507336HCID 178507336, Verbindung

Produkt 1

HCID 16069044HCID 16069044, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
Katalysator
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

The product of Example 101A (cis-2-(3-piperidin-1-yl-cyclobutyl)-benzothiazole-6-ylamine) (50 mg, 0.174 mmole), 5-bromopyrimidine (42 mg, 0.264 mmole), tris(dibenzylideneacetone)dipalladium (0) (6.5 mg, 0.007 mmole), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, 8.7 mg, 0.014 mmole) and sodium tert-butoxide (23 mg, 0.242 mmole) were charged in a tube and sealed. The tube was placed on high vacuum for 2 hours and refilled with nitrogen. Toluene (2 mL) was added and the reaction vessel was placed in a microwave reactor and heated at 145° C. for 15 minutes. After cooling to room temperature, the mixture was diluted with water and extracted three times with dichloromethane. The combined organic layers were concentrated and the crude product was purified by column chromatography (0.4% ammonium hydroxide and 4% methanol in dichloromethane). The product collected was a mixture of cis and trans isomers. 1H NMR (400 MHz, CDCl3) δ ppm 8.79 (s, 1H) 8.50-8.56 (m, 2H) 7.89 (d, J=8.90 Hz, 1H) 7.58 (d, J=2.15 Hz, 1H) 7.18 (dd, J=8.59, 2.15 Hz, 1H) 5.83 (s, 1H) 3.48-3.63 (m, 1H) 2.73-2.85 (m, 1H) 2.59-2.71 (m, 2H) 2.23-2.39 (m, 6H) 1.54-1.66 (m, 4H) 1.41-1.51 (m, 2H). MS: (M+H)+=366.

Aufarbeitung

  1. customsealed
  2. additionrefilled with nitrogen
  3. customthe reaction vessel was placed in a microwave reactor
  4. temperatureAfter cooling to room temperature
  5. extractionextracted three times with dichloromethane
  6. concentrationThe combined organic layers were concentrated
  7. customthe crude product was purified by column chromatography (0.4% ammonium hydroxide and 4% methanol in dichloromethane)
  8. customThe product collected
  9. additiona mixture of cis and trans isomers

Quellen und Nachweise

ORD-Eintrag
ord-585622fd7f2b40a097960c915a0eeac0
Quelldatensatz
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08592467B2

Notizen zur Reaktion

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