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

HRID 1186539Notes

Reaction equation

HRID 1186539 reaction equation
C(OC(=O)[NH:7][CH2:8][CH:9]([NH:15][C:16]1[N:21]=[C:20]([C:22]2[N:26]3[CH:27]=[CH:28][N:29]=[C:30]([N:31]4[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33][CH2:32]4)[C:25]3=[N:24][CH:23]=2)[CH:19]=[CH:18][N:17]=1)[C:10]1[CH:14]=[CH:13][S:12][CH:11]=1)(C)(C)C.Cl>C(O)C>[CH3:37][N:34]1[CH2:33][CH2:32][N:31]([C:30]2[C:25]3[N:26]([C:22]([C:20]4[CH:19]=[CH:18][N:17]=[C:16]([NH:15][CH:9]([C:10]5[CH:14]=[CH:13][S:12][CH:11]=5)[CH2:8][NH2:7])[N:21]=4)=[CH:23][N:24]=3)[CH:27]=[CH:28][N:29]=2)[CH2:36][CH2:35]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68226841(2-{4-[8-(4-Methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamino}-2-thiophen-3-yl-ethyl)-carbamic acid tert-butyl ester

Product 1

HCID 66546330N1-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-1-thiophen-3-yl-ethane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of crude (2-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamino}-2-thiophen-3-yl-ethyl)-carbamic acid tert-butyl ester (150 mg, 0.280 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 N1-{4-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-yl}-1-thiophen-3-yl-ethane-1,2-diamine; hydrochloride. (Yield 13 mg, 5.57%). 1H NMR (300 MHz, CD3OD): δ 8.81 (brs, 1H), 8.63 (s, 1H), 8.29 (d, 1H, J=6.0 Hz), 7.61-7.52 (m, 3H), 7.46-7.43 (m, 1H), 7.23 (d, 1H, J=5.1 Hz), 5.72 (brs, 1H), 5.47-5.43 (m, 2H), 3.63-3.60 (m, 4H), 3.50-3.48 (m, 2H), 3.29-3.26 (m, 2H), 2.89 (s, 3H). LC-MS: [M+H]+ 436.

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-35d65739f2e94d1f94806a9b54541d5d
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

Loading…