N,N-dimethyl-2-piperazin-1-ylethanamine

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,4-Bis-benzyloxy-5-isopropyl-benzoyl chloride (200 mg, 0.5 mmol) was dissolved in DCM (5 ml), treated with 1-(2-dimethylaminoethyl)piperazine (83.6 mg, 0.53 mmol) and triethylamine (0.2 ml, then stirred for 1 hour at room temperature. The reaction mixture was diluted with DCM, washed with water and, dried (MgSO4) and evaporated to give 0.25 g of the title compound. MS: [M+H]+ 516. washed with water dried (MgSO4) evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-iodoquinolin-2(1H)-one (48 mg) in an oven-dried flask was added 18-crown-6 (34 mg), sodium t-butoxide (13 mg), tris(dibenzylideneacetone)dipalladium (0) (8.3 mg) and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (17 mg) and the flask carefully filled with argon. The N,N-dimethyl-N-(2-piperazin-1-ylethyl)amine (17 mg) and THF (2 mL) were then added and the reaction stirred at rt for 16 h. The reaction mixture was then filtered and concentrated and the residue purified by reverse phase HPLC to yield the title compound. 1H NMR (500 Hz, CDCl3): δ 7.62-7.35 (m, 8H); 6.74 (d, J=2.3 Hz, 1H); 6.49 (d, J=9.8 Hz, 1H); 5.86 (d, J=2.1 Hz, 1H); 3.16 (t, J=4.8 Hz, 4H); 2.57 (t, J=5.1 Hz, 4H); 2.53-2.46 (m, 4H), 2.28 (s, 6H). Mass spectrum: m/z 557 (M+H). the flask carefully filled with argon The reaction mixture was then filtered concentrated the residue purified by reverse phase HPLC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-({4-[2-(dimethylamino)ethyl]piperazin-1yl}sulfonyl)-3-(4-methoxybenzyl)-3,4-dihydroquinazolin-2(1H)-one was prepared from 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-sulfonyl chloride (COMPOUND CCC8) and N,N-dimethyl-2-piperazin-1-ylethanamine by a procedure analogous to that described in EXAMPLE CCC25, STEP B. Mass spectrum (ESI) 742 (M+1).