[4-(3-{6-[(Thiophen-2-ylmethyl)-amino]-pyridin-2-yl}-imidazo[1,2-a]pyrazin-8-ylamino)-cyclohexyl]-carbamic acid tert-butyl ester → N-(3-{6-[(thiophen-2-ylmethyl)-amino]-pyridin-2-yl}-imidazo[1,2-a]pyrazin-8-yl)-cyclohexane-1,4-diamine

HRID 1186565Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186565
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][CH:27]=[C:26]([NH:30][CH2:31][C:32]5[S:33][CH:34]=[CH:35][CH:36]=5)[N:25]=4)=[CH:22][N:23]=3)[CH:18]=[CH:19][N:20]=2)[CH2:10][CH2:9]1)(C)(C)C>C(O)C.Cl>[S:33]1[CH:34]=[CH:35][CH:36]=[C:32]1[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][CH:27]=1

Komponenten

4

Edukt 1

HCID 68227100[4-(3-{6-[(Thiophen-2-ylmethyl)-amino]-pyridin-2-yl}-imidazo[1,2-a]pyrazin-8-ylamino)-cyclohexyl]-carbamic acid tert-butyl ester

Produkt 1

HCID 66546703N-(3-{6-[(thiophen-2-ylmethyl)-amino]-pyridin-2-yl}-imidazo[1,2-a]pyrazin-8-yl)-cyclohexane-1,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

The mixture of [4-(3-{6-[(thiophen-2-ylmethyl)-amino]-pyridin-2-yl}-imidazo[1,2-a]pyrazin-8-ylamino)-cyclohexyl]-carbamic acid tert-butyl ester (100 mg, 0.193 mmol) in ethanol (4 mL) and concentrated HCl (4 mL) was stirred at room temperature overnight. The reaction mixture was then concentrated under reduced pressure. The residue was purified by prepara-HPLC to give N-(3-{6-[(thiophen-2-ylmethyl)-amino]-pyridin-2-yl}-imidazo[1,2-a]pyrazin-8-yl)-cyclohexane-1,4-diamine; hydrochloride. (Yield 30 mg). 1HNMR (300 MHz, CD3OD): δ 8.59-8.56 (m, 1H), 8.38 (brs, 1H), 7.82 (d, 1H, J=9.0 Hz), 7.42-7.34 (m, 1H), 7.16-7.04 (m, 2H), 6.98-6.85 (m, 2H), 6.43-6.39 (m, 1H), 4.70 (d, 2H, J=5.1 Hz), 3.89-3.85 (m, 1H), 3.23-3.07 (m, 1H), 2.20-2.05 (m, 4H), 1.60-1.37 (m, 4H). LC-MS: [M+H]+ 420.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe residue was purified by prepara-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d0a48cff6dbc46179be07d1cd29cb98f
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673905B2

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