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Cesium carbonate → HCID 86731737, Verbindung

HRID 1504868
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1504868
Br[C:2]1[CH:3]=[C:4]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]2[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:5]=[N:6][C:7]=1[C:8]#[N:9].[NH2:25][C:26]1[N:31]=[C:30]([CH3:32])[C:29]([C:33]#[N:34])=[CH:28][CH:27]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>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]>[C:8]([C:7]1[N:6]=[CH:5][C:4]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]2[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:3][C:2]=1[NH:25][C:26]1[CH:27]=[CH:28][C:29]([C:33]#[N:34])=[C:30]([CH3:32])[N:31]=1)#[N:9]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 27946626-Amino-2-methylpyridine-3-carbonitrileHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86716545tert-butyl (1S,2R)-2-(5-bromo-6-cyanopyridin-3-ylamino)cyclohexylcarbamate

Produkt 1

HCID 86731737HCID 86731737, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a flask containing tert-butyl {(1S,2R)-2-[(5-bromo-6-cyanopyridin-3-yl)amino]cyclohexyl}carbamate (PrepEx 1.1) (120 mg, 0.30 mmol), 6-amino-2-methylpyridine-3-carbonitrile (40 mg, 0.30 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (29 mg, 0.061 mmol), Pd2(dba)3 (28 mg, 0.031 mmol) and cesium carbonate (198 mg, 0.609 mmol) was added degassed dioxane (3 mL). The reaction mixture was heated to 100° C. overnight. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and water, and the organic layer was separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by chromatography on silica gel (0-40% ethyl acetate/hexanes, linear gradient) afforded tert-butyl [(1S,2R)-2-({6-cyano-5-[(5-cyano-6-methylpyridin-2-yl)amino]pyridin-3-yl}amino)cyclohexyl]carbamate. MS ESI calc'd for C24H30N7O2 [M+H]+ 448. found 448. 1H NMR (500 MHz, DMSO-d6) δ 9.62 (s, 1H), 7.92-7.86 (m, 2H), 7.26 (s, 1H), 6.81 (d, J=8.8 Hz, 1H), 6.64 (d, J=8.5 Hz, 1H), 6.56 (d, J=7.7 Hz, 1), 3.75-3.64 (m, 2H), 2.47 (s, 3H), 1.75-1.42 (m, 8H), 1.26 (s, 9H).

Aufarbeitung

  1. additionwas added
  2. customdegassed dioxane (3 mL)
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additiondiluted with ethyl acetate and water
  5. customthe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification by chromatography on silica gel (0-40% ethyl acetate/hexanes, linear gradient)

Quellen und Nachweise

ORD-Eintrag
ord-9e5760f3c6494ffb9e5796e727f82a97
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09216173B2

Notizen zur Reaktion

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