4-Bromobenzoyl chloride → HCID 9850132, compound

HRID 458527Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

3-benzyl-2-(1-{[2-(dimethylamino)ethyl]amino}propyl)-3,5,6,7-tetrahydro-4H-cyclopenta[d]pyrimidin-4-one (1-4, 0.070 g, 0.20 mmol) was dissolved in CH2Cl2 (1.0 mL) and treated successively with 4-bromo-benzoylchloride (0.052 g, 0.24 mmol) and TEA (0.08 mL, 0.59 mmol). The reaction was stirred at 25° C. for 1 hour. The reaction was diluted with CH2Cl2 (10 mL), washed with 5% NaHCO3 and dried over MgSO4. The organics were concentrated under reduced pressure and subjected to preparative thin layer chromatography (SiO2, 5% MeOH/CH2Cl2) to provide N-[1-(3-benzyl-4-oxo-4,5,6,7-tetrahydro-3H-cyclopenta[d]pyrimidin-2-yl) propyl]-4-bromo-N-[2-(dimethylamino)ethyl]benzamide (1-5). 1H NMR (300 MHz, CDCl3) δ 7.53 (d, J=8.2 Hz, 2H), 7.31 (m, 5H), 12 (d, J=8.0 Hz, 2H), 5.98 (d, J=15.6 Hz, 1H), 5.85 (m, 1H), 4.99 (d, J=15.8 Hz, 1H), 3.36 (m, 2H), 2.90 (m, 4H), 2.10 (m, 4 H), 1.87 (s, 6H), 1.80 (m, 1H), 1.63 (m, 1H), 0.62 (m, 3H); MS 537.2 found, 537.5 required.

Workup

washwashed with 5% NaHCO3
dry with materialdried over MgSO4
concentrationThe organics were concentrated under reduced pressure

Sources & evidence

ORD record: ord-27a5773577de46e98913aa5411fea0d7
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192949B2

Reaction notes

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