Hydrochloric Acid → N1-{6-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyridin-2-yl}-1-phenyl-ethane-1,2-diamine

HRID 1186509Notes

Reaction equation

HRID 1186509 reaction equation
C(OC(=O)[NH:7][CH2:8][CH:9]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[N:27]3[CH:28]=[CH:29][N:30]=[C:31]([N:32]4[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]4)[C:26]3=[N:25][CH:24]=2)[N:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.Cl>C(O)C>[CH3:38][N:35]1[CH2:34][CH2:33][N:32]([C:31]2[C:26]3[N:27]([C:23]([C:19]4[N:18]=[C:17]([NH:16][CH:9]([C:10]5[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=5)[CH2:8][NH2:7])[CH:22]=[CH:21][CH:20]=4)=[CH:24][N:25]=3)[CH:28]=[CH:29][N:30]=2)[CH2:37][CH2:36]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68226762(2-{6-[8-(4-Methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyridin-2-ylamino}-2-phenyl-ethyl)-carbamic acid tert-butyl ester

Product 1

HCID 66548626N1-{6-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyridin-2-yl}-1-phenyl-ethane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of (2-{6-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyridin-2-ylamino}-2-phenyl-ethyl)-carbamic acid tert-butyl ester (30 mg, 0.06 mmol) and concentrated HCl (3 mL) in ethanol (3 mL) was stirred at room temperature for 15 hours. The reaction mixture was then concentrated under reduced pressure to give N1-{6-[8-(4-methyl-piperazin-1-yl)-imidazo[1,2-a]pyrazin-3-yl]-pyridin-2-yl}-1-phenyl-ethane-1,2-diamine; hydrochloride. (Yield 40 mg). 1HNMR (300 MHz, CD3OD): δ 8.54 (brs, 1H), 8.13 (s, 1H), 7.64-7.46 (m, 3H), 7.31-7.10 (m, 5H), 6.92 (d, 1H, J=8.1 Hz), 5.44 (brs, 3H), 3.93 (brs, 2H), 3.72-3.69 (m, 2H), 3.52-3.34 (m, 4H), 2.92 (s, 3H). LC-MS: [M+H]+ 429.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-c8a66478abf643629f4abb3ead173b25
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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