Water → HCID 86670920, compound

HRID 1186493Notes

Reaction equation

HRID 1186493 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][N:15]=[C:16](Cl)[C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1.[N:18]1([CH2:24][CH2:25][NH2:26])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.CCN(CC)CC.O>CC(O)C>[Br:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][N:15]=[C:16]([NH:26][CH2:25][CH2:24][N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 4082852-MorpholinoethylamineHCID 86670917HCID 86670917, compound

Product 1

HCID 86670920HCID 86670920, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 3-(6-bromo-pyridin-2-yl)-8-chloro-imidazo[1,2-a]pyrazine (from Example 38 supra) (3.09 g, 10.0 mmol), 2-morpholin-4-yl-ethylamine (2.6 g, 20.0 mmol), NEt3 (2.02 g, 20.0 mmol) in 2-propanol (300 mL) was stirred and heated at reflux for 16 hours. The solution was then cooled to room temperature and poured into water. The resulted solid was filtered and washed with water. The crude product was purified by chromatography (CH2Cl2:CH3OH, 20:1) to give [3-(6-bromo-pyridin-2-yl)-imidazo[1,2-a]pyrazin-8-yl]-(2-morpholin-4-yl-ethyl)-amine. (Yield 2.5 g, 62%). LC-MS: [M+H]+ 403.

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 hours
  3. filtrationThe resulted solid was filtered
  4. washwashed with water
  5. customThe crude product was purified by chromatography (CH2Cl2:CH3OH, 20:1)

Sources & evidence

ORD record
ord-487c966197a540cc8e558966c93f51ef
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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