[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 1186565노트

반응식

HRID 1186565 반응식
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

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-d0a48cff6dbc46179be07d1cd29cb98f
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673905B2

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