Hydrochloric Acid → N-{3-[2-(2-amino-1-phenyl-ethylamino)-pyrimidin-4-yl]-imidazo[1,2-a]pyrazin-8-yl}-cyclohexane-1,4-diamine

HRID 1186543노트

반응식

HRID 1186543 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][N:27]=[C:26]([NH:30][CH:31]([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)[CH2:32][NH:33]C(OC(C)(C)C)=O)[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>[NH2:33][CH2:32][CH: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:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 68227159(4-{3-[2-(2-Tert-butoxycarbonylamino-1-phenyl-ethylamino)-pyrimidin-4-yl]-imidazo[1,2-a]pyrazin-8-ylamino}-cyclohexyl)-carbamic acid tert-butyl ester

생성물 1

HCID 66546334N-{3-[2-(2-amino-1-phenyl-ethylamino)-pyrimidin-4-yl]-imidazo[1,2-a]pyrazin-8-yl}-cyclohexane-1,4-diamine

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of crude (4-{3-[2-(2-tert-butoxycarbonylamino-1-phenyl-ethylamino)-pyrimidin-4-yl]-imidazo[1,2-a]pyrazin-8-ylamino}-cyclohexyl)-carbamic acid tert-butyl ester (100 mg, 0.16 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-(2-amino-1-phenyl-ethylamino)-pyrimidin-4-yl]-imidazo[1,2-a]pyrazin-8-yl}-cyclohexane-1,4-diamine; hydrochloride. (Yield 26 mg, 16.3%). 1H NMR (300 MHz, CD3OD): δ 8.68 (s, 2H), 8.46 (brs, 1H), 7.63-7.61(m, 3H), 7.46-7.32(m, 4H), 5.78 (s, 1H), 4.05 (brs, 1H), 3.61-3.48(m, 2H), 3.23 (brs, 1H), 2.22 (brs, 4H), 1.76-1.71(m, 4H).

후처리

  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

출처 및 근거

ORD 기록
ord-2adf30421db24e7fae0fa4356d1c02db
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673905B2

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