HCID 22288411, compound → HCID 5329429, compound

HRID 968247Notes

Reaction equation

CS([C:5]1[N:10]=[C:9]([N:11]2[CH:15]=[CH:14][N:13]=[C:12]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:8]=[CH:7][N:6]=1)(=O)=O.[C:22]([N:25]1[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:33]=[C:34]([CH:36]=[C:37]([CH3:39])[CH:38]=2)[NH2:35])[CH2:27][CH2:26]1)(=[O:24])[CH3:23]>CO.C(Cl)Cl>[C:22]([N:25]1[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:33]=[C:34]([NH:35][C:5]3[N:10]=[C:9]([N:11]4[CH:15]=[CH:14][N:13]=[C:12]4[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:8]=[CH:7][N:6]=3)[CH:36]=[C:37]([CH3:39])[CH:38]=2)[CH2:27][CH2:26]1)(=[O:24])[CH3:23]

Participants

Conditions

Temperature: 130 °C

Procedure

2-(Methylsulfonyl)-4-(2-phenyl-1H-imidazol-1-yl)pyrimidine (1-3, 100 mg, 0.33 mmol) and 3-[(4-acetylpiperazin-1-yl)methyl]-5-methylaniline (240 mg) were combined neat and heated to 130° C. After 2 hours the mixture was cooled to room temperature. Flash column chromatography (gradient, 2-5% MeOH/CH2Cl2) gave the title compound as an off-white foam. 1H-NMR (300 MHz, CDCl3) δ 8.26 (d, J=5.5 Hz, 1H), 7.68 (d, J=1.53 Hz, 1H), 7.50 (m, 2H), 7.40 (m, 4H), 7.30 (s, 1H), 7.16 (s, 1H), 6.86 (s, 1H), 6.25 (d, J=5.49 Hz, 1H), 3.64 (t, J=5.19 Hz, 2H), 4H), 3.46 (m, 4H), 2.44 (m, 4H), 2.35 (s, 3H), 2.08 (s, 3H).

Workup

temperatureAfter 2 hours the mixture was cooled to room temperature

Sources & evidence

ORD record: ord-df30eb9f7097492f82ce0e5bc662ab61
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06958340B2

Reaction notes

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