3-[(4-Methylpiperazin-1-yl)methyl]aniline → 8-Indan-5-yl-2-[3-(4-methyl-piperazin-1-ylmethyl)-phenylamino]-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid amide

HRID 1989028Notes

Reaction equation

HRID 1989028 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:15]4[N:16]=[C:17](S(C)(=O)=O)[N:18]=[CH:19][C:14]=4[C:13](=[O:24])[C:12]([C:25]([NH2:27])=[O:26])=[CH:11]3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH3:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:35][C:36]2[CH:37]=[C:38]([NH2:42])[CH:39]=[CH:40][CH:41]=2)[CH2:31][CH2:30]1>CC(O)C>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[C:15]4[N:16]=[C:17]([NH:42][C:38]5[CH:39]=[CH:40][CH:41]=[C:36]([CH2:35][N:32]6[CH2:31][CH2:30][N:29]([CH3:28])[CH2:34][CH2:33]6)[CH:37]=5)[N:18]=[CH:19][C:14]=4[C:13](=[O:24])[C:12]([C:25]([NH2:27])=[O:26])=[CH:11]3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 64841863-[(4-Methylpiperazin-1-yl)methyl]anilineHCID 686788178-Indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid amide

Product 1

HCID 160594798-Indan-5-yl-2-[3-(4-methyl-piperazin-1-ylmethyl)-phenylamino]-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid amide (from Example 23 (b), 7 mg) in 1 mL of i-PrOH was added 3-(4-methyl-piperazin-1-ylmethyl)-phenylamine (5 mg). The mixture was stirred at 90° C. for 1 hr. After cooling down, the solvent was evaporated and the product was purified chromatographically (CH2Cl2/CH3OH/NH4OH (10:1:0.1, v/v)). The title compound was obtained as white solid (2.7 mg, 29%). 1H NMR (400 MHz, CDCl3) δ (ppm): 9.39 (br, 1H), 9.34 (s, 1H), 8.76 (s, 1H), 7.48 (br, 1H), 7.35 (d, J=8.0 Hz, 1H), 7.29 (br, 1H), 7.17 (s, 1H), 7.12 (d, J=8.0 Hz, 1H), 6.94 (br, 2H), 5.67 (br, 1H), 3.29 (br, 2H), 3.00 (t, J=7.3 Hz, 2H), 2.92 (t, J=7.3 Hz, 2H), 2.49 (br, 7H), 2.33 (br, 4H), 2.15 (m, 2H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C29H31N7O2: 510.25 (M+H), Found: 510.1.

Workup

  1. temperatureAfter cooling down
  2. customthe solvent was evaporated
  3. customthe product was purified chromatographically (CH2Cl2/CH3OH/NH4OH (10:1:0.1

Sources & evidence

ORD record
ord-793cd672c0fe4e6287b7b5d3eb488ff1
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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