4-(4-Methylpiperazin-1-yl)aniline → HCID 46701028, compound

HRID 1188712Notes

Reaction equation

HRID 1188712 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([N:12]1[C:17]3[N:18]=[C:19](S(C)=O)[N:20]=[CH:21][C:16]=3[CH:15]=[CH:14][C:13]1=[O:25])[CH2:9][CH2:8]2.[CH3:26][N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=2)[CH2:29][CH2:28]1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([N:12]1[C:17]3[N:18]=[C:19]([NH:37][C:36]4[CH:35]=[CH:34][C:33]([N:30]5[CH2:29][CH2:28][N:27]([CH3:26])[CH2:32][CH2:31]5)=[CH:39][CH:38]=4)[N:20]=[CH:21][C:16]=3[CH:15]=[CH:14][C:13]1=[O:25])[CH2:9][CH2:8]2

Participants

4

Reactant 2

HCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 66760404HCID 66760404, compound

Product 1

HCID 46701028HCID 46701028, compoundYield 8.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-(7-methoxy-2,3-dihydro-1H-inden-1-yl)-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one (0.29 g, 0.81 mmol) and 4-(4-methylpiperazino)aniline (0.15 g, 0.81 mmol) were stirred at 140° C. for 4 h. The reaction mixture was dissolved in dichloromethane (35 mL) and washed with 10% sodium hydroxide solution (1×15 mL) then with water (1×15 mL). The organic layer was dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel column chromatography using dichloromethane:methanol (9:1) to give 8-(7-methoxy-2,3-dihydro-1H-inden-1-yl)-2-(4-(4-methylpiperazin-1-yl)phenylamino)pyrido[2,3-d]pyrimidin-7(8H)-one (32 mg, 0.07 mmol, 8.6%) as the major product. ESMS m/z 483 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 9.81 (br. s., 1H), 8.73 (s, 1H), 7.77 (d, J=9.3 Hz, 1H), 7.61 (d, J=9.0 Hz, 2H), 7.14 (t, J=7.5 Hz, 1H), 6.89 (d, J=9.0 Hz, 2H), 6.87 (br.s., 1H), 6.84 (d, J=7.3 Hz, 1H), 6.65 (d, J=8.3 Hz, 1H), 6.13 (d, J=9.3 Hz, 1H), 3.43 (s, 3H), 3.10-3.00 (m, 4H), 3.00-2.85 (m, 2H), 2.45-2.38 (m, 4H), 2.35-2.25 (m, 2H), 2.20 (s, 3H).

Workup

  1. washwashed with 10% sodium hydroxide solution (1×15 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ac431b0464664eb8b55239770ac107f3
Source dataset
uspto-grants-2014_03
Patent number
US08674095B2

Reaction notes

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