Reaction SMILES: O1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][C:10]2[N:15]=[CH:14][C:13]([C:16]3[N:17]=[C:18]([C:23]4[O:24][C:25]([C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)=[N:26][N:27]=4)[C:19]([NH2:22])=[N:20][CH:21]=3)=[CH:12][CH:11]=2)[CH2:3]C1.COC1C=NC=CC=1C1N=C(C2OC(C3C=CC=CC=3)=NN=2)C(N)=NC=1.COC1N=CC(C2N=C(C3OC(C4C=CC=CC=4)=NN=3)C(N)=NC=2)=CC=1.CN(C)CCOC1C=C(C2N=C(C3OC(C4C=CC=CC=4)=NN=3)C(N)=NC=2)C=CN=1.C1(C2OC(C3C(N)=NC=C(C4C=NC(N5CCNCC5)=CC=4)N=3)=NN=2)C=CC=CC=1.NC1N=CC(C2C=CN=C(NCCN(C)C)C=2)=NC=1C1OC(C2C=CC=CC=2)=NN=1.CN(C)CCCOC1N=CC(C2N=C(C3OC(C4C=CC=CC=4)=NN=3)C(N)=NC=2)=CC=1.O1CCN(C2N=CC(C3N=C(C4OC(C5C=CC=CC=5)=NN=4)C(N)=NC=3)=CC=2)CC1>>[CH3:3][N:4]1[CH2:7][CH2:8][N:9]([C:10]2[N:15]=[CH:14][C:13]([C:16]3[N:17]=[C:18]([C:23]4[O:24][C:25]([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=5)=[N:26][N:27]=4)[C:19]([NH2:22])=[N:20][CH:21]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1
Reactant: Nc1ncc(-c2ccc(NCCN3CCOCC3)nc2)nc1-c1nnc(-c2ccccc2)o1
Agent: CN(C)CCCOc1ccc(-c2cnc(N)c(-c3nnc(-c4ccccc4)o3)n2)cn1
Agent: CN(C)CCNc1cc(-c2cnc(N)c(-c3nnc(-c4ccccc4)o3)n2)ccn1
Agent: CN(C)CCOc1cc(-c2cnc(N)c(-c3nnc(-c4ccccc4)o3)n2)ccn1
Product: CN1CCN(c2ccc(-c3cnc(N)c(-c4nnc(-c5ccccc5)o4)n3)cn2)CC1

Procedure:
Compound IA-72 5-[6-(2-morpholinoethylamino)-3-pyridyl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine 1H NMR (400.0 MHz, CDCl3) d 3.17 (br s, 4H), 3.29 (t, 2H), 3.92-3.94 (m, 6H), 7.03 (d, 1H), 7.51-7.58 (m, 3H), 8.18-8.21 (m, 2H), 8.38 (d, 1H), 8.49 (s, 1H) and 8.52 (s, 1H) ppm; MS (ES+) 445.2 Compound IA-86 5-(3-methoxy-4-pyridyl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine 1H NMR (400.0 MHz, DMSO) d 4.09 (s, 3H), 7.66-7.72 (m, 3H), 7.96 (br s, 2H), 8.12 (br d, 1H), 8.17 (dd, 2H), 8.47 (d, 1H), 8.64 (s, 1H) and 9.03 (s, 1H) ppm; MS (ES+) 347.1 Compound IA-117 5-(6-methoxy-3-pyridyl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine 1H NMR (400.0 MHz, DMSO) d 3.93 (s, 3H), 6.99 (d, 1H), 7.67-7.73 (m, 5H), 8.17-8.20 (m, 2H), 8.42 (dd, 1H), 8.93 (d, 1H) and 8.95 (s, 1H) ppm; MS (ES+) 347.1 Compound IA-165 5-[2-(2-dimethylaminoethyloxy)-4-pyridyl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine 1H NMR (400.0 MHz, DMSO) d 2.23 (s, 6H), 2.65 (t, 2H), 4.41 (t, 2H), 7.49 (s, 1H), 7.69-7.73 (m, 4H), 7.95 (br s, 2H), 8.16-8.19 (m, 2H), 8.28 (d, 1H) and 9.07 (s, 1H) ppm; MS (ES+) 404.1 Compound IA-186 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-(6-piperazin-1-yl-3-pyridyl)pyrazin-2-amine 1H NMR (400.0 MHz, DMSO) d 3.00 (br d, 4H), 3.58 (br t, 4H), 6.86 (d, 1H), 7.42-7.48 (m, 5H), 7.94 (dd, 2H), 8.09 (dd, 1H), 8.53 (br s, 2H), 8.68 (s, 1H) and 8.69 (d, 1H) ppm Compound IA-265 N′-[4-[5-amino-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-2-pyridyl]-N,N-dimethyl-ethane-1,2-diamine 1H NMR (400.0 MHz, DMSO) d 2.20 (s, 6H), 2.45 (t, 2H), 3.41 (q, 2H), 6.54 (t, 1H), 7.18 (dd, 1H), 7.21 (s, 1H), 7.67-7.74 (m, 3H), 7.86 (br s, 2H), 8.08 (d, 1H), 8.18 (dd, 2H) and 8.89 (s, 1H) ppm; MS (ES+) 403.2 Compound IA-279 5-[6-[3-(dimethylamino)propoxy]-3-pyridyl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine 1H NMR (400.0 MHz, DMSO) d 1.89 (quin, 2H), 2.16 (s, 6H), 2.36 (t, 2H), 4.35 (t, 2H), 6.96 (d, 1H), 7.68-7.71 (m, 5H), 8.17-8.19 (m, 2H), 8.40 (dd, 1H), 8.91 (d, 1H) and 8.94 (s, 1H) ppm; MS (ES+) 418.2 Compound IA-283 5-(6-morpholino-3-pyridyl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-amine 1H NMR (400.0 MHz, DMSO) d 3.33-3.35 (m, 4H), 3.52-3.54 (m, 4H), 6.79 (d, 1H), 7.42-7.51 (m, 5H), 7.95-7.97 (m, 2H), 8.07 (dd, 1H) and 8.69 (s, 2H) ppm; MS (ES+) 402.1