Hydrochloric Acid → N-[3-(2-benzylamino-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-cyclohexane-1,4-diamine

HRID 1186527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186527
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:16]3[N:17]([C:21]([C:24]4[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH2:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[N:25]=4)=[CH:22][N:23]=3)[CH:18]=[CH:19][N:20]=2)[CH2:10][CH2:9]1)(C)(C)C.Cl>C(O)C>[CH2:31]([NH:30][C:26]1[N:25]=[C:24]([C:21]2[N:17]3[CH:18]=[CH:19][N:20]=[C:15]([NH:14][CH:11]4[CH2:12][CH2:13][CH:8]([NH2:7])[CH2:9][CH2:10]4)[C:16]3=[N:23][CH:22]=2)[CH:29]=[CH:28][N:27]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 68227103{4-[3-(2-Benzylamino-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

Produkt 1

HCID 66546142N-[3-(2-benzylamino-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-cyclohexane-1,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of crude {4-[3-(2-benzylamino-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (400 mg, 0.182 mmol) in ethanol (5 mL) was added concentrated hydrochloric acid (5 mL) slowly. The reaction mixture was stirred at room temperature for 15 hours. The solvent was removed under reduced pressure and then the solid was purified by prep-HPLC. Several drops of concentrated HCl were added to the fractions with product. After sonicating for several minutes, solution was concentrated under reduced pressure to afford N-[3-(2-benzylamino-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-cyclohexane-1,4-diamine; hydrochloride. (Yield 33 mg, 28.9%). 1H NMR (300 MHz, CD3OD): δ 8.73 (s, 1H), 8.45 (brs, 2H), 7.61-7.32 (m, 7H), 4.91 (brs, 2H), 4.11 (brs, 1H), 3.25 (brs, 1H), 2.23 (brs, 4H), 1.77-1.75 (m, 4H). LC-MS: [M+H]+ 415.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe solid was purified by prep-HPLC
  3. additionSeveral drops of concentrated HCl were added to the fractions with product
  4. customAfter sonicating for several minutes
  5. concentrationsolution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-33b7ca9b90ac458f94e18cbc11c1338d
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673905B2

Notizen zur Reaktion

Wird geladen…