Reaction SMILES: [Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:24])[N:7]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:8]([CH2:12][N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)=[N:9]2)=[CH:4][C:3]=1[CH2:25][N:26]([C:30]1[CH:42]=[CH:41][C:33]([C:34]([O:36]C(C)(C)C)=O)=[CH:32][CH:31]=1)[CH2:27][C:28]#[CH:29].[NH2:43][CH2:44][C:45]1[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl.FC(F)(F)C(O)=O.CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:24])[N:7]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:8]([CH2:12][N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)=[N:9]2)=[CH:4][C:3]=1[CH2:25][N:26]([C:30]1[CH:42]=[CH:41][C:33]([C:34]([NH:43][CH2:44][C:45]2[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=2)=[O:36])=[CH:32][CH:31]=1)[CH2:27][C:28]#[CH:29]
Reactant: NCc1cccnc1
Reactant: C#CCN(Cc1cc2c(=O)n(CC(=O)OC)c(CN3CCCCC3)nc2cc1Cl)c1ccc(C(=O)OC(C)(C)C)cc1
Agent: F[P-](F)(F)(F)(F)F
Agent: c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1
Solvent: ClCCl
Solvent: CN(C)C=O
Solvent: O=C(O)C(F)(F)F
Product: C#CCN(Cc1cc2c(=O)n(CC(=O)OC)c(CN3CCCCC3)nc2cc1Cl)c1ccc(C(=O)NCc2cccnc2)cc1
Reaction time: 0.05 h

Procedure:
A solution of tert-butyl 4-[N-[7-chloro-3-methoxycarbonylmethyl-4-oxo-2-piperidin-1-ylmethyl-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (0.087 g, 0.14 mmol) (Preparation Example 31) in dichloromethane (1.7 ml) and trifluoroacetic acid (2.3 ml) was stirred at room temperature for 55 min with protection from the light. The solvents was then removed in vacuo and the residue was triturated with ether and dried in vacuo ovcr P2O5. This solid was dissolved in anhydrous DMF (5 ml) under argon and the solution was placed in an ice-bath. A solution of 3-(aminomethyl)pyridine (0.024 g, 0.22 mmol) in DMF (0.2 ml) was then added followed by PyBOP® (0.082 g, 0.16 mmol) and dilsopropylethylamine (0.171 g, 1.3 mmol). Stirring was continued at 0° C. for 3 min; then the ice-bath was removed and the reaction mixture was stirred for an additional 3 h at room temperature before being partitioned between ethyl acetate (200 ml) and saturated aqueous bicarbonate (100 ml). The organic layer was washed with more saturated aqueous bicarbonate (100 ml) and the combined aqueous washings were extracted with ethyl acetate (2×50 ml). The combined ethyl acetate extracts were washed with brine (100 ml), dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography using a gradient of methanol in chloroform (0 to 3%) as eluant, then reprecipitated from dichloromethane/hexane to give a white solid which was collected by filtration, washed with hexane and dried in vacuo over P2O5 (0.036 g, 39%), mp 214-216° C.; 1H-NMR (DMSO-d6) 1.36 (m, 6H, piperidine CH2CH2CH2), 2.32 (m, 4H, piperidine CH2NCH2), 3.20(s, 1H, C≡CH), 3.58 (s, 2H, 2-CH2), 3.67 (s, 3H, CO2Me), 4.38 (s, 2H, CH,C≡C), 4.45 (d, J=5.7 Hz, 2H, CONHCH2), 4.78 (s, 2H, 6-CH2), 4.87(s, 2H, N3—CH2), 6.79 (d, J=8.8 Hz, 2H, 3,5′-ArH), 7.32 (dd, J=4.6, 7.8 Hz, 1H, pyr 5-H), 7.68 (d, J=7.7 Hz, 1H, pyr 4-H), 7.75 (d, J=8.7 Hz, 2H, 2′,6′-ArH), 7.85, 7.91 (2×s, 2H, 5-H, 8-H), 8.43 (d, J=3.6 Hz, 1H, pyr 6-H), 8.52 (s, 1H, pyr 2-H), 8.74 (t, J=5.9 Hz, 1H, CONH).; MS (FAB, m/z) 627, 629 [(M+H)+, 100%, 38% respectively; Cl isotopic pattern]. FAB-HRMS: measured 627.2504; calculated for C34H36ClN6O2 (M+H)+: 627.2487.