4-(4-Ethylpiperazin-1-yl)aniline → HCID 16123801, compound

HRID 886800Notes

Reaction equation

[CH2:1]([N:3]1[C:8]2[N:9]=[C:10](S(C)(=O)=O)[N:11]=[C:12]([CH3:13])[C:7]=2[CH:6]=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:4]1=[O:24])[CH3:2].[CH2:25]([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)[CH3:26]>CS(C)=O>[CH2:1]([N:3]1[C:8]2[N:9]=[C:10]([NH:37][C:36]3[CH:35]=[CH:34][C:33]([N:30]4[CH2:29][CH2:28][N:27]([CH2:25][CH3:26])[CH2:32][CH2:31]4)=[CH:39][CH:38]=3)[N:11]=[C:12]([CH3:13])[C:7]=2[CH:6]=[C:5]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:4]1=[O:24])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

8-Ethyl-4-methyl-2-(methylsulfonyl)-6-phenylpyrido[2,3-d]pyrimidin-7(8H)-one (275 mg, 0.80 mmol) and 4-(4-ethylpiperazin-1-yl)aniline (197 mg, 1.2 equiv.) were added to dimethyl sulfoxide (5 mL) and the resulting mixture was heated to 100° C. and stirred overnight. After cooling to room temperature, the reaction was partitioned between aqueous and organic layers with ethyl acetate and H2O, organic layer was dried with anhydrous magnesium sulfate, filtered and evaporated, and directly applied to prep-LC to provide the title compound in (210.0 mg, 56% yield): 1H NMR (400 MHz, CDCl3): δ 7.80 (s, 1H), 7.62 (d, 2H), 7.60 (d, 2H), 7.40 (m, 2H), 7.18 (s, 1H), 6.95 (d, 2H), 4.50 (q, 2H), 3.22 (m, 4H), 2.70 (m, 4H), 2.60 (s, 3H), 2.50 (m, 2H), 1.40 (t, 3H), 1.20 (t, 3H); MS (EI) for C28H32N6O: 469.10 (MH+).

Workup

temperatureAfter cooling to room temperature
customthe reaction was partitioned between aqueous and organic layers with ethyl acetate and H2O, organic layer
dry with materialwas dried with anhydrous magnesium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-5b053878b1694d1a8cacd49462cb534f
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247408B2

Reaction notes

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