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 1186543Notes

Reaction equation

HRID 1186543 reaction equation
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

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-2adf30421db24e7fae0fa4356d1c02db
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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