HCID 68227083, compound → N-{3-[6-(2-chloro-benzylamino)-pyridin-2-yl]-imidazo[1,2-a]pyrazin-8-yl}-cyclohexane-1,4-diamine

HRID 1186561Notes

Reaction equation

HRID 1186561 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][CH:35]=[CH:34][C:33]=5[Cl:38])[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:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[CH2:31][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[CH2:10][CH2:9][CH:8]([NH2:7])[CH2:13][CH2:12]4)[C:16]3=[N:23][CH:22]=2)[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 1

HCID 68227083HCID 68227083, compound

Product 1

HCID 66546525N-{3-[6-(2-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

The mixture of (4-{3-[6-(2-chloro-benzylamino)-pyridin-2-yl]-imidazo[1,2-a]pyrazin-8-ylamino}-cyclohexyl)-carbamic acid tert-butyl ester (227 mg, 0.41 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-(2-chloro-benzylamino)-pyridin-2-yl]-imidazo[1,2-a]pyrazin-8-yl}-cyclohexane-1,4-diamine; hydrochloride. (Yield 60 mg). 1HNMR (300 MHz, CD3OD): δ 8.25 (d, 1H, J=5.7 Hz), 8.19 (s, 1H), 7.88 (t, 1H, J=8.7 Hz), 7.53-7.50 (m, 2H), 7.35-7.22 (m, 3H), 7.10 (d, 1H, J=5.7 Hz), 7.02 (d, 1H, J=8.7 Hz), 4.77 (s, 2H), 4.05 (brs, 1H), 3.32 (brs, 1H), 2.23 (brs, 4H), 1.81-1.74 (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-10669eac100548369da8c091da6401b1
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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