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Hydrochloric Acid → HCID 10297844, Verbindung

HRID 861131
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 861131
[CH:1]1([NH:6][C:7]2[N:12]3[N:13]=[C:14]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([N:34]=C(C5C=CC=CC=5)C5C=CC=CC=5)[CH:29]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]5[CH2:27][CH2:26][CH2:25][CH2:24]5)[N:17]=4)=[C:11]3[CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(=O)(O)[O-]>O1CCCC1.CCOCC>[NH2:34][C:30]1[CH:29]=[C:28]([C:14]2[C:15]([C:16]3[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]4[CH2:24][CH2:25][CH2:26][CH2:27]4)[N:17]=3)=[C:11]3[CH:10]=[CH:9][CH:8]=[C:7]([NH:6][CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[N:12]3[N:13]=2)[CH:33]=[CH:32][CH:31]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 769Bicarbonate IonHCID 57494736HCID 57494736, Verbindung

Produkt 1

HCID 10297844HCID 10297844, VerbindungAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×
HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-{3-[(diphenylmethylene)amino]phenyl}-pyrazolo[1,5-a]pyridin-7-amine (2.61 g, 4.22 mmol) in tetrahydrofuran (30 mL) at 0° C. was added 4N hydrochloric acid (20 mL) dropwise. Subsequently, the reaction mixture was stirred for 5 minutes. The reaction mixture was diluted with ether, then saturated aqueous bicarbonate was added slowly till the ether layer turned clear. The resulting mixture was stirred for 30 minutes. The phases were separated, the organic phase was washed with water, brine and dried (magnesium sulfate). Filtration and concentration of the filtrate to a solid, followed by recrystallization from ethyl acetate-hexanes, gave 2-(3-aminophenyl)-N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-7-amine (1.78 g, 93%) as a pale yellow solid. 1H NMR (CDCl3): δ 7.92 (d, 1H), 7.82 (d, 1H), 7.32 (t, 1H), 7.22 (m, 2H), 7.00–6.94 (m, 2H), 6.78 (m, 1H), 6.34 (d, 1H), 6.04 (m, 2H), 4.38 (m, 1H), 4.00 (m, 1H), 3.75 (broad, 2H), 2.14–2.05 (m, 4H), 1.83–1.54 (m, 12H); MS m/z 454 (M+1).

Aufarbeitung

  1. stirringThe resulting mixture was stirred for 30 minutes
  2. customThe phases were separated
  3. washthe organic phase was washed with water, brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationFiltration and concentration of the filtrate to a solid
  6. customfollowed by recrystallization from ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e695110f36f84b0f8f90cf1af53783ec
Quelldatensatz
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07153855B2

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