HCID 68226974, compound → N-{3-[6-(4-chloro-benzylamino)-pyridin-2-yl]-imidazo[1,2-a]pyrazin-8-yl}-cyclohexane-1,4-diamine

HRID 1186563Notes

Reaction equation

HRID 1186563 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][CH:27]=[C:26]([NH:30][CH2:31][C:32]5[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=5)[N:25]=4)=[CH:22][N:23]=3)[CH:18]=[CH:19][N:20]=2)[CH2:10][CH2:9]1)(C)(C)C>C(O)C.Cl>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][NH:30][C:26]2[N:25]=[C:24]([C:21]3[N:17]4[CH:18]=[CH:19][N:20]=[C:15]([NH:14][CH:11]5[CH2:10][CH2:9][CH:8]([NH2:7])[CH2:13][CH2:12]5)[C:16]4=[N:23][CH:22]=3)[CH:29]=[CH:28][CH:27]=2)=[CH:33][CH:34]=1

Participants

4

Reactant 1

HCID 68226974HCID 68226974, compound

Product 1

HCID 66546701N-{3-[6-(4-chloro-benzylamino)-pyridin-2-yl]-imidazo[1,2-a]pyrazin-8-yl}-cyclohexane-1,4-diamine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of (4-{3-[6-(4-chloro-benzylamino)-pyridin-2-yl]-imidazo[1,2-a]pyrazin-8-ylamino}-cyclohexyl)-carbamic acid tert-butyl ester (214 mg, 0.39 mmol) in ethanol (4 mL) and concentrated HCl (4 mL) was stirred at room temperature overnight. The reaction mixture was then concentrated under reduced pressure. The residue was purified by preparative-HPLC to give N-{3-[6-(4-chloro-benzylamino)-pyridin-2-yl]-imidazo[1,2-a]pyrazin-8-yl}-cyclohexane-1,4-diamine; hydrochloride. (Yield 80 mg). 1HNMR (300 MHz, CD3OD): δ 8.22 (d, 1H, J=5.7 Hz), 8.19 (s, 1H), 7.89 (t, 1H, J=8.7 Hz), 7.46-7.39 (m, 4H), 7.23 (d, 1H, J=6.9 Hz), 7.17 (d, 1H, J=5.7 Hz), 7.02 (d, 1H, J=8.7 Hz), 4.70 (s, 2H), 4.04 (brs, 1H), 3.25 (brs, 1H), 2.23 (brs, 4H), 1.81-1.71 (m, 4H). LC-MS: [M+H]+ 448.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe residue was purified by preparative-HPLC

Sources & evidence

ORD record
ord-7b1048ce326743dd8c92e965e2e11cf4
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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