Isopropanol → HCID 86662394, compound

HRID 1188720Notes

Reaction equation

HRID 1188720 reaction equation
[ClH:1].[CH3:2][N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH2:18])=[NH:17])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.[OH-].[Na+].[CH:21](O)([CH3:23])[CH3:22]>>[Cl:1][C:22]1[N:6]=[CH:9][C:10]([C:11]2[CH:12]=[CH:13][N:18]=[C:16]([NH:15][C:12]3[CH:11]=[CH:10][C:9]([N:6]4[CH2:7][CH2:8][N:3]([CH3:2])[CH2:4][CH2:5]4)=[CH:14][CH:13]=3)[N:17]=2)=[CH:23][CH:21]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 178480748HCID 178480748, compound

Product 1

HCID 86662394HCID 86662394, compoundYield 33%

Procedure

4.22 g 1-(6-Chloro-pyridin-3-yl)-3-dimethylamino-propenone (20 mmol) was dissolved in 100 mL isopropanol, 5.92 g N-[4-(4-Methyl-piperazin-1-yl)-phenyl]-guanidine hydrochloride (20 mmol) and 0.96 g sodium hydroxide (24 mmol) were added and heated at reflux for 18 h. The mixture was allowed to cool to room temperature and stirred at room temperature for three days. The yellow-green precipitate was filtered to give [4-(6-Chloro-pyridin-3-yl)-pyrimidin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (2.50 g, Y=33%). Purity: 94% (LCMS); 1H NMR (400 MHz, DMSO-d6) δ ppm 9.49 (s, 1H), 9.14 (d, J=2.5 Hz, 1H), 8.54 (d, J=5.3 Hz, 1H), 8.52 (dd, J=8.5, 2.5 Hz, 1H), 7.70 (d, J=8.5 Hz, 1H), 7.60 (d, J=9.0 Hz, 2H), 7.41 (d, J=5.3 Hz, 1H), 6.91 (d, J=9.0 Hz, 2H), 3.03-3.10 (m, 4H), 2.42-2.47 (m, 4H), 2.22 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. filtrationThe yellow-green precipitate was filtered

Sources & evidence

ORD record
ord-7d1f01012232406a9e41eab8bf99a7e5
Source dataset
uspto-grants-2014_03
Patent number
US08674095B2

Reaction notes

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