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Ethyl Acetate → HCID 178433731, Verbindung

HRID 1909060
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1909060
CN(C[N:5]1[C:9]2=[N:10][C:11]([N:14]3[CH2:19][CH2:18][CH:17]([N:20]([CH3:22])[CH3:21])[CH2:16][CH2:15]3)=[CH:12][CH:13]=[C:8]2[N:7]=[CH:6]1)C.C(NC(C)C)(C)C.[Li].C[O:32][C:33](=O)[C:34]1[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[C:36]([C:42]2[C:46]([CH3:47])=[N:45][N:44]3[CH2:48][CH2:49][CH2:50][C:43]=23)[CH:35]=1.CCOC(C)=O>C1COCC1>[CH3:22][N:20]([CH3:21])[CH:17]1[CH2:16][CH2:15][N:14]([C:11]2[N:10]=[C:9]3[NH:5][C:6]([C:33]([C:34]4[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[C:36]([C:42]5[C:46]([CH3:47])=[N:45][N:44]6[CH2:48][CH2:49][CH2:50][C:43]=56)[CH:35]=4)=[O:32])=[N:7][C:8]3=[CH:13][CH:12]=2)[CH2:19][CH2:18]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 45051747Lithium diisopropylamineHCID 66599667[1-(3-dimethylaminomethyl-3H-imidazo[4,5-b]pyridin-5-yl)-piperidin-4-yl]-dimethyl-amineHCID 66599721HCID 66599721, Verbindung

Produkt 1

HCID 178433731HCID 178433731, VerbindungAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of [1-(3-dimethylaminomethyl-3H-imidazo[4,5-b]pyridin-5-yl)-piperidin-4-yl]-dimethyl-amine (0.36 g, 1.2 mmol) in THF (5 mL) at −78° C. under N2 was added dropwise a freshly prepared solution of lithium diisopropylamine (1M, 1.5 mL, 1.5 mmol) in THF. After 10 m at −78° C. a solution of 4-cyano-3-(2-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-benzoic acid methyl ester (0.28 g, 1.0 mmol) in THF (5 mL) was added. The reaction mixture was stirred at −78° C. under N2 for 15 m before quenching with a 1:1 solution of acetic acid and water (2 mL). After warming to room temperature the quenched reaction was diluted several fold EtOAc and washed with dilute NH4OH followed by brine. The organic layer was dried over Na2SO4, filtered and concentrated. After purifying the crude product by reverse phase HPLC, the product was neutralized with aqueous Na2CO3 yielding the desired product as a orange-colored solid (50 mg, 0.10 mmol). 1H NMR (400 MHz, DMSO-d6) □ ppm 1.32-1.44 (m, J=12.00, 11.81, 11.81, 3.79 Hz, 2H) 1.85 (d, J=10.61 Hz, 2H) 2.20 (s, 6H) 2.25 (s, 3H) 2.33-2.46 (m, 1H) 2.53-2.63 (m, 2H) 2.89-3.02 (m, 4H) 4.43 (d, J=13.14 Hz, 2H) 7.04 (d, J=9.09 Hz, 1H) 7.95 (d, J=9.09 Hz, 1H) 8.10 (d, J=8.08 Hz, 1H) 8.36 (d, J=7.58 Hz, 1H) 8.52 (s, 1H); MS m/z 495.5 (M+H)+.

Aufarbeitung

  1. custombefore quenching with a 1:1 solution of acetic acid and water (2 mL)
  2. temperatureAfter warming to room temperature
  3. customthe quenched reaction
  4. washwashed with dilute NH4OH
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customAfter purifying the crude product by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d2e0f81039e14b6b8378f55b6c401c1a
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08598217B2

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