Diisopropylethylamine → HCID 10297834, compound

HRID 968256Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

2-Chloro-4-(2-phenyl-1H-imidazol-1-yl)pyrimidine (56 mg, 0.22 mmol) and 3-[(4-acetylpiperazin-1-yl)methyl]aniline (142 mg, 0.61 mmol) were mixed and heated neat to 100° C. After 2 hours the reaction was heated to 120° C. for 1 hour then to 140° C. for 1 hour. N,N-di-iso-propylethylamine (0.076 ml, 0.44 mol) was added and the reaction was heated for an additional 1.5 hours. The reaction was cooled, diluted with DMSO and directly purified by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA) to afford the title compound. 1H NMR (300 MHz, CDCl3) δ 8.29 (d, J=5.2 Hz, 1H), 7.67 (d, J=1.5 Hz, 1H), 7.52 (m, 3H), 7.41 (m, 4H), 7.25 (m, 2H), 7.02 (d, J=7.8 Hz, 1H), 6.30 (d, J=5.1 Hz, 1H), 3.63 (t, J=5.5 Hz, 2H), 3.52 (s, 2H), 3.47 (m, 2H), 2.45 (m, 4H), 2.08 (s, 3H).

Workup

temperatureAfter 2 hours the reaction was heated to 120° C. for 1 hour
temperaturethe reaction was heated for an additional 1.5 hours
temperatureThe reaction was cooled
customdirectly purified by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA)

Sources & evidence

ORD record: ord-bac4b0bb4ccf4b0fa3a23230b4c5106f
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06958340B2

Reaction notes

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