2-Chlorobenzylamine → HCID 66546705, compound

HRID 1186566Notes

Reaction equation

HRID 1186566 reaction equation
CS([C:5]1[N:10]=[C:9]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([NH:20][CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[C:14]3=[N:13][CH:12]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[Cl:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32][NH2:33]>>[Cl:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32][NH:33][C:5]1[N:10]=[C:9]([C:11]2[N:15]3[CH:16]=[CH:17][N:18]=[C:19]([NH:20][CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[C:14]3=[N:13][CH:12]=2)[CH:8]=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 666482-ChlorobenzylamineHCID 68227155HCID 68227155, compound

Product 1

HCID 66546705HCID 66546705, compound

Conditions

Temperature
140 °C

Procedure

A mixture of [3-(2-methanesulfonyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-(2-morpholin-4-yl-ethyl)-amine (from Example 50 supra) (200 mg, 0.50 mmol) and 2-chlorobenzylamine (281 mg, 1.99 mmol) was heated at 140° C. with stirring for 2 hours. The oil was purified by chromatography (silica gel, 10 g, 200-300 mesh, eluting with dichloromethane:methanol 50:1 to 20:1) to afford the crude product (110 mg). Then the crude product was purified by prep-HPLC. Several drops of concentrated HCl were added to the fractions with product. After sonicating for several minutes, solution was concentrated under reduced pressure to afford {3-[2-(2-chloro-benzylamino)-pyrimidin-4-yl]-imidazo[1,2-a]pyrazin-8-yl}-(2-morpholin-4-yl-ethyl)-amine; hydrochloride. (Yield 58 mg, 25.1%). 1H NMR (300 MHz, CD3OD): δ 8.72 (s, 1H), 8.51 (s, 1H), 8.35 (s, 1H), 7.59 (d, 1H, J=6.9 Hz), 7.46-7.28 (m, 5H), 4.75 (brs, 2H), 4.17 (brs, 2H), 3.93 (brs, 4H), 3.59-3.28 (m, 5H). LC-MS: [M+H]+ 466.

Workup

  1. customThe oil was purified by chromatography (silica gel, 10 g, 200-300 mesh, eluting with dichloromethane:methanol 50:1 to 20:1)
  2. customto afford the crude product (110 mg)
  3. customThen the crude product was purified by prep-HPLC
  4. additionSeveral drops of concentrated HCl were added to the fractions with product
  5. customAfter sonicating for several minutes
  6. concentrationsolution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-78fd91b7d5f94f6c91c817eda3d25fca
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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