HCID 22648179, compound → HCID 22648041, compound

HRID 394121Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18](=[O:29])[CH2:19][N:20]2[CH2:25][CH2:24][N:23]([CH:26]([CH3:28])[CH3:27])[CH2:22][CH2:21]2)[CH:15]=[C:14]2[C:9]=1[CH2:10][N:11](CC1C=CC(OC)=CC=1)[C:12](=[O:38])[N:13]2[C:30]1[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=1[Cl:37]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:18](=[O:29])[CH2:19][N:20]2[CH2:21][CH2:22][N:23]([CH:26]([CH3:28])[CH3:27])[CH2:24][CH2:25]2)[CH:15]=[C:14]2[C:9]=1[CH2:10][NH:11][C:12](=[O:38])[N:13]2[C:30]1[C:31]([Cl:37])=[CH:32][CH:33]=[CH:34][C:35]=1[Cl:36]

Participants

Conditions

Temperature: 70 °C

Procedure

5-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-7-[(4-isopropylpiperazin-1-yl)acetyl]-3-(4-methoxybenzyl)-3,4-dihydroquinazolin-2(1H)-one (36 mg, 0.052 mmol) was dissolved in trifluoroacetic acid (0.8 mL), and this mixture was heated at 70° C. for 30 min. After cooling it down, trifluoroacetic acid was removed by co-evaporation with toluene to give crude product. This was purified by preparative thin layer chromatography using 5% 2M NH3 in MeOH/CH2Cl2 as an eluent to give the title compound. 1H NMR (CDCl3, 500 MHz): δ 7.54-7.29 (m, 8H); 6.94 (s, 1H); 5.44 (s, 1H); 4.47 (d, J=15.6 Hz, 1H); 4.29 (d, J=15.6 Hz, 1H); 3.54 (Abq, J=4.1, 14.9 Hz, 2H); 2.62 (m, 1H); 2.48 (brs, 8H); 1.03 (2 s, 6H). Mass spectrum (ESI): 571.2 (M+1).

Workup

temperatureAfter cooling it down
customtrifluoroacetic acid was removed by co-evaporation with toluene
customto give crude product
customThis was purified by preparative thin layer chromatography

Sources & evidence

ORD record: ord-b722e992aef443edafb1c4a955b39119
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809199B2

Reaction notes

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