Benzylamine → HCID 66546148, compound

HRID 1186532Notes

Reaction equation

HRID 1186532 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.[CH2:29]([NH2:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH2:29]([NH:36][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)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 68227155HCID 68227155, compound

Product 1

HCID 66546148HCID 66546148, compound

Conditions

Temperature
140 °C

Procedure

The 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) (120 mg, 0.30 mmol) and benzylamine (128 mg, 1.19 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, 30:1 to 10:1) to afford the crude product (100 mg). 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-benzylamino-pyrimidin-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-(2-morpholin-4-yl-ethyl)-amine; hydrochloride. (Yield 25 mg, 19.5%). 1H NMR (300 MHz, CD3OD): δ 8.77 (s, 1H), 8.57-8.38 (m, 2H), 7.62 (d, 1H, J=6.6 Hz), 7.48-7.34 (m, 6H), 4.82 (brs, 2H), 4.21 (brs, 2H), 3.99 (brs, 4H), 3.63-3.47 (m, 6H). LC-MS: [M+H]+ 431.

Workup

  1. customThe oil was purified by chromatography (silica gel, 10 g, 200-300 mesh, eluting with dichloromethane:methanol, 30:1 to 10:1)
  2. customto afford the crude product (100 mg)
  3. customThe 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-31135ef1b4c14f8b9e83154a87b65b0c
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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