HCID 68226737, compound → N-{3-[6-(3-chloro-benzylamino)-pyridin-2-yl]-imidazo[1,2-a]pyrazin-8-yl}-cyclohexane-1,4-diamine

HRID 1186555Notes

Reaction equation

HRID 1186555 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]=[C:34]([Cl:38])[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:34]1[CH:33]=[C:32]([CH:37]=[CH:36][CH:35]=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 68226737HCID 68226737, compound

Product 1

HCID 66546519N-{3-[6-(3-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-(3-chloro-benzylamino)-pyridin-2-yl]-imidazo[1,2-a]pyrazin-8-ylamino}-cyclohexyl)-carbamic acid tert-butyl ester (430 mg, 0.78 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 obtained crude product was purified by preparative-HPLC to give N-{3-[6-(3-chloro-benzylamino)-pyridin-2-yl]-imidazo[1,2-a]pyrazin-8-yl}-cyclohexane-1,4-diamine; hydrochloride. (Yield 100 mg). 1H NMR (300 MHz, CD3OD): δ 8.16-8.13 (m, 2H), 7.91 (t, 1H, J=8.1 Hz), 7.46 (s, 1H), 7.38-7.31 (m, 3H), 7.22-7.17 (m, 2H), 7.04 (d, 1H, J=8.7 Hz), 4.69 (s, 2H), 4.06 (s, 1H), 3.23 (brs, 1H), 2.21 (brs, 4H), 1.76-1.70 (m, 4H). LC-MS: [M+H]+ 448.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe obtained crude product
  3. customwas purified by preparative-HPLC

Sources & evidence

ORD record
ord-ca9ed1ba266342ec9aa2a3127d55291e
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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