Hydrochloric Acid → N1-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-1-phenyl-propane-1,3-diamine

HRID 1186507Notes

Reaction equation

HRID 1186507 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH:10]([NH:17][C:18]1[N:23]=[C:22]([C:24]2[N:28]3[CH:29]=[CH:30][N:31]=[C:32]([N:33]4[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]4)[C:27]3=[N:26][CH:25]=2)[CH:21]=[CH:20][N:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(C)(C)C.Cl>C(O)C>[CH3:39][N:36]1[CH2:35][CH2:34][N:33]([C:32]2[C:27]3[N:28]([C:24]([C:22]4[CH:21]=[CH:20][N:19]=[C:18]([NH:17][CH:10]([C:11]5[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=5)[CH2:9][CH2:8][NH2:7])[N:23]=4)=[CH:25][N:26]=3)[CH:29]=[CH:30][N:31]=2)[CH2:38][CH2:37]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68226593(3-{4-[8-(4-Methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamino}-3-phenyl-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 66548624N1-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-1-phenyl-propane-1,3-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of crude (3-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamino}-3-phenyl-propyl)-carbamic acid tert-butyl ester (51 mg, 0.094 mmol) in ethanol (3 mL) was added concentrated hydrochloric acid (3 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 N1-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-1-phenyl-propane-1,3-diamine; hydrochloride. (Yield 59 mg, 100%).

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-8f17357661424844a113a82dea9972e0
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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