dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-573e8af24c15454793a5a9bb824c9cdf | Brc1cnc(Nc2ccc(OCCN3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2csc(C(N)=O)c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>>N.NC(=O)c1cc(-c2cnc(Nc3ccc(OCCN4CCOCC4)cc3)c3ncnn23)cs1 | CC1(OB(OC1(C)C)C=1C=C(SC1)C(=O)N)C.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.C(=O)([O-])[O-].[Na+].[Na+].BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)OCCN2CCOCC2>>N.O1CCN(CC1)CCOC1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2 | Br[c:8]1[cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[cH:26][cH:27]2)[c:28]2[n:29][cH:30][n:31][n:32]12.CC1(C)OB(c2csc(C(=O)[NH2:1])c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-[c:7]4[cH:6][c:5]([C:3]([NH2:2])=[O:4])[s:34][cH:33]4)n4ncnc34)cc2)CC1>>[NH3:1... | Brc1cnc(Nc2ccc(OCCN3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2csc(C(N)=O)c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1 | N.NC(=O)c1cc(-c2cnc(Nc3ccc(OCCN4CCOCC4)cc3)c3ncnn23)cs1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1 | C-C Coupling | OtherReaction | 5d4ca946d437df36dd96fd1b6d9c8cdde8fc4524e5bae3cb1f7cc44766204f15 | 96e5f3628c1bd4659dd3e9821904115decf673d0e8e42bb7900b7f521b084c51 | c1nc2c(Nc3ccc(OCCN4CCOCC4)cc3)ncc(-c3ccsc3)n2n1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-c2:c:s:c(-C(=O)-[NH2;D1;+0:10]):c:2)-O-C-1(-C)-C.C-N1-C-C-N(-c2:c:c:c(-N-c3:n:c:c(-[c;H0;D3;+0:11]4:[c:12]:[#16;a:13]:[c:14](-[C:15](-[N;D1;H2:16])=[O;D1;H0:17]):[c:18]:4):n4:n:c:n:c:3:4):c:c:2)-C-C-1>>[N;D1;H2:16]-[C:15](... | 52 | [{"value": 52.0, "product": "O1CCN(CC1)CCOC1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4, using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-amine (113 mg, 0.27 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiophene-2-carboxamide (136 mg, 0.537 mmol), and Pd(PPh3)4 (78 mg, 0.067 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amide.Secondary amine.Tertiary amine.Tertiary amine.Boronic ester | null | c1cn2ncnc2cn1.B1OCCO1.c1ccsc1.C1CNCCN1.c1ccccc1.c1ccsc1.c1cn2ncnc2cn1 | c1ccsc1.c1cn2ncnc2cn1 | c1ccsc1.c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1 | null | null | Brc1cnc(Nc2ccc(OCCN3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2csc(C(N)=O)c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1>N.NC(=O)c1cc(... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a9c6a97dd90f40e88c5dd30e4580df9e | Brc1cnc(Nc2ccc(OCCN3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2ccc(C(N)=O)s2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>>N.NC(=O)c1ccc(-c2cnc(Nc3ccc(OCCN4CCOCC4)cc3)c3ncnn23)s1 | CC1(OB(OC1(C)C)C1=CC=C(S1)C(=O)N)C.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.C(=O)([O-])[O-].[Na+].[Na+].BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)OCCN2CCOCC2>>N.O1CCN(CC1)CCOC1=CC=C(C=C1)NC=1C=2N(C(=CN1)C1=CC=C(S1)C(=O)N)N=CN2 | Br[c:9]1[cH:10][n:11][c:12]([NH:13][c:14]2[cH:15][cH:16][c:17]([O:18][CH2:19][CH2:20][N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[cH:27][cH:28]2)[c:29]2[n:30][cH:31][n:32][n:33]12.CC1(C)OB([c:8]2[cH:7][cH:6][c:5]([C:3]([NH2:2])=[O:4])[s:34]2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(=O)[NH2:1])c4)n4ncnc34)cc2)CC1>>[NH3:1... | Brc1cnc(Nc2ccc(OCCN3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2ccc(C(N)=O)s2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1 | N.NC(=O)c1ccc(-c2cnc(Nc3ccc(OCCN4CCOCC4)cc3)c3ncnn23)s1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1 | C-C Coupling | OtherReaction | 5d4ca946d437df36dd96fd1b6d9c8cdde8fc4524e5bae3cb1f7cc44766204f15 | 96e5f3628c1bd4659dd3e9821904115decf673d0e8e42bb7900b7f521b084c51 | c1csc(-c2cnc(Nc3ccc(OCCN4CCOCC4)cc3)c3ncnn23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10]2:[#16;a:11]:[c:12](-[C:13](-[N;D1;H2:14])=[O;D1;H0:15]):[c:16]:[c:17]:2)-O-C-1(-C)-C.C-N1-C-C-N(-c2:c:c:c(-N-c3:n:c:c(-c4:c:s:c(-C(=O)-[NH2;D1;+0:18]):c:4):n4:n:c:n:c:3:4):c:c:2)-C-C-1>>[N;D1;H2:14]-[C:13](... | 25 | [{"value": 25.0, "product": "O1CCN(CC1)CCOC1=CC=C(C=C1)NC=1C=2N(C(=CN1)C1=CC=C(S1)C(=O)N)N=CN2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4, using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-amine (118 mg, 0.28 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiophene-2-carboxamide (142 mg, 0.56 mmol), and Pd(PPh3)4 (81 mg, 0.07 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amide.Secondary amine.Tertiary amine.Tertiary amine.Boronic ester | null | c1cn2ncnc2cn1.B1OCCO1.c1ccsc1.C1CNCCN1.c1ccccc1.c1ccsc1.c1cn2ncnc2cn1 | c1ccsc1.c1cn2ncnc2cn1 | c1ccsc1.c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1 | null | null | Brc1cnc(Nc2ccc(OCCN3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2ccc(C(N)=O)s2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1>N.NC(=O)c1ccc... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f528335182e4588bf47d51a6b6245a2 | C1=COCCC1.c1cn[nH]c1>>c1cnn(C2CCCCO2)c1 | N1N=CC=C1.O1CCCC=C1>>O1C(CCCC1)N1N=CC=C1 | [CH:5]1=[CH:6][CH2:7][CH2:8][CH2:9][O:10]1.[cH:1]1[cH:2][n:3][nH:4][cH:11]1>>[cH:1]1[cH:2][n:3][n:4]([CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][O:10]2)[cH:11]1 | C1=COCCC1.c1cn[nH]c1 | c1cnn(C2CCCCO2)c1 | null | [H-].[Na+].C(=O)(C(F)(F)F)O | null | Heteroatom Alkylation and Arylation | OtherReaction | 1ec778c8f54d7ad18e95009f54038d9cdb57b9e363777849f1433a4ce7a5e2cb | c37c4c64b8e0c6e5b39694c16f8c97245b55f05530ce8b5df4dfb3a695b50244 | c1cnn(C2CCCCO2)c1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[nH;D2;+0:5]:1.[#8:6]1-[C:7]-[C:8]-[C:9]-[CH;D2;+0:10]=[CH;D2;+0:11]-1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[n;H0;D3;+0:5]:1-[CH;D3;+0:11]1-[#8:6]-[C:7]-[C:8]-[C:9]-[CH2;D2;+0:10]-1 | 104.2 | [{"value": 99.0, "product": "O1C(CCCC1)N1N=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.2, "product": "O1C(CCCC1)N1N=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 5 | HOUR | 1H-Pyrazole (14.3 g, 0.21 mol) is dissolved in 3,4-dihydro-2H-pyran (26.74 g, 0.32 mol) in the presence of a catalytic amount of TFA (0.1 mL, 1.3 mmol). The reaction mixture is stirred at 95° C. for 5 hours, cooled and then quenched using NaH (0.2 g, 5 mmol). The solvent is removed to give the title compound as a brown... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ether | C1=COCCC1.c1cn[nH]c1 | c1cn[nH]c1.C1CCOCC1 | c1cn[nH]c1.C1CCOCC1 | null | [H-].[Na+].C(=O)(C(F)(F)F)O | 95 | 5 | C1=COCCC1.c1cn[nH]c1>[H-].[Na+].C(=O)(C(F)(F)F)O>c1cnn(C2CCCCO2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-033ea64afce44276a7c4dac91d4384c8 | CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.Nc1ccc(N2CCOCC2)cc1.OB(O)N1CC=CN1>>c1cc(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c3ncnn23)[nH]n1 | CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.N1N(CC=C1)B(O)O.C(=O)([O-])[O-].[Na+].[Na+].N1(CCOCC1)C1=CC=C(C=C1)N>>N1(CCOCC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1NN=CC1)N=CN2 | CN1CCN(c2cc[c:9]([NH:8][c:7]3[n:6][cH:5][c:4](-[c:3]4cs[c:1](C(N)=O)[cH:2]4)[n:25]4[c:21]3[n:22][cH:23][n:24]4)[cH:20]c2)CC1.Nc1c[cH:19][c:12]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[cH:11][cH:10]1.OB(O)[N:26]1CC=C[NH:27]1>>[cH:1]1[cH:2][c:3](-[c:4]2[cH:5][n:6][c:7]([NH:8][c:9]3[cH:10][cH:11][c:12]([N:13]4[CH2:... | CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.Nc1ccc(N2CCOCC2)cc1.OB(O)N1CC=CN1 | c1cc(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c3ncnn23)[nH]n1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CN(C)C=O.C(=O)(O)[O-].[Na+] | Miscellaneous | OtherReaction | 382fe5a33715f095223f38950c48bec08e32887180f353c786d0a7db211a916e | 76c182260d9c73fd569006c43f3814f68c8d83080194fb7784bbe2c269a8e6b9 | c1cc(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c3ncnn23)[nH]n1 | C-N1-C-C-N(-c2:c:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[#7:3]-[c:4]3:[#7;a:5]:[c:6]:[c:7](-[c;H0;D3;+0:8]4:[c:9]:[c;H0;D3;+0:10](-C(-N)=O):s:c:4):[#7;a:11]4:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:4:3):c:c:2)-C-C-1.N-c1:[cH;D2;+0:16]:[c:17]:[c:18](-[#7:19]):[cH;D2;+0:20]:c:1.O-B(-O)-[N;H0;D3;+0:21]1-C-C=C-[NH;D2;+0:22]-1>>[#7:19]-[c:... | null | [] | 100 | CELSIUS | 18 | HOUR | This compound may be prepared using methods as described for Compound 6, step 4, using 5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(morpholin-4-yl)-phenyl]-amine (100 mg, 0.267 mmol), 1H-pyrazole-2-boronic acid (60 mg, 0.535 mmol), Pd(PPh3)4 (93 mg, 0.08 mmol) and Na2CO3 (88 mg, 0.80 mmol) in DMF (2 mL). The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Hydrazine.Primary amide.Primary amine.Tertiary amine.Tertiary amine | null | C1CNCCN1.c1ccccc1.c1ccsc1.c1ccccc1.C1=CN[NH]C1 | c1cn[nH]c1.c1ccccc1 | c1cn[nH]c1.c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C)C=O.C(=O)(O)[O-].[Na+] | 100 | 18 | CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.Nc1ccc(N2CCOCC2)cc1.OB(O)N1CC=CN1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C)C=O.C(=O)(O)[O-].[Na+]>c1cc(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e19017422ab14010904dfe523c48205d | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cn2)CC1.CC1(C)OB(c2csc(C(N)=O)c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>>CC(C)N1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.N | CC1(OB(OC1(C)C)C=1C=C(SC1)C(=O)N)C.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.C(=O)([O-])[O-].[Na+].[Na+].BrC1=CN=C(C=2N1N=CN2)NC=2C=NC(=CC2)N2CCN(CC2)C(C)C>>N.C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2 | Br[c:16]1[cH:15][n:14][c:13]([NH:12][c:11]2[cH:10][cH:9][c:8]([N:7]3[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:33][CH2:32]3)n[cH:30]2)[c:29]2[n:25]1[n:26][cH:27][n:28]2.CC1(C)OB([c:17]2[cH:18][s:19][c:20]([C:21]([NH2:22])=[O:23])[cH:24]2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(=O)[NH2:34])c4)n4ncnc34)c[cH:31]2)CC1>>[... | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cn2)CC1.CC1(C)OB(c2csc(C(N)=O)c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1 | CC(C)N1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.N | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1 | C-C Coupling | OtherReaction | cf5549799cc4acd18ed81259f1840ced3dc52c62c8411c2248454740f4743d6e | 96e5f3628c1bd4659dd3e9821904115decf673d0e8e42bb7900b7f521b084c51 | c1nc2c(Nc3ccc(N4CCNCC4)cc3)ncc(-c3ccsc3)n2n1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](-[#7:5]-[c:6]2:[c:7]:[c:8]:[c;H0;D3;+0:9](-[#7:10](-[C:11])-[C:12]):n:[cH;D2;+0:13]:2):[c:14]2:[#7;a:15]:[c:16]:[#7;a:17]:[#7;a:18]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:19]2:[c:20]:[#16;a:21]:[c:22](-[C:23](-[N;D1;H2:24])=[O;D1;H0:25]):[c:26]:2)-O-C-1(-C)-C.C-N1-C-C-N(-c2:[cH;D2;+0:27]:... | 61 | [{"value": 61.0, "product": "C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4, using 5-bromo-N-(6-(4-isopropylpiperazin-1-yl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine (100 mg, 0.24 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiophene-2-carboxamide (121 mg, 0.48 mmol), and Pd(PPh3)4 (69 mg, 0.05... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amide.Secondary amine.Tertiary amine.Tertiary amine.Boronic ester | null | c1ccncc1.c1cn2ncnc2cn1.B1OCCO1.c1ccsc1.C1CNCCN1.c1ccccc1.c1ccsc1.c1cn2ncnc2cn1 | c1ccccc1.c1ccsc1.c1cn2ncnc2cn1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccsc1.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1 | null | null | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cn2)CC1.CC1(C)OB(c2csc(C(N)=O)c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1>CC(C)N1CC... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4682667b785a4aff8b0f28ad39cf080c | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnc(N(C(=O)OC(C)(C)C)c2ccc(N3CCOCC3)cc2)c2ncnn12.NC(=O)c1coc(Br)c1>>CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2cc(C(N)=O)co2)n2ncnc12.N | BrC1=CC(=CO1)C(=O)N.C(C)(C)(C)OC(N(C=1C=2N(C(=CN1)[Sn](CCCC)(CCCC)CCCC)N=CN2)C2=CC=C(C=C2)N2CCOCC2)=O>>N.C(C)(C)(C)OC(N(C1=CC=C(C=C1)N1CCOCC1)C=1C=2N(C(=CN1)C=1OC=C(C1)C(N)=O)N=CN2)=O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:24]1[cH:23][n:22][c:21]([N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:9]2[cH:10][cH:11][c:12]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[cH:19][cH:20]2)[c:37]2[n:33]1[n:34][cH:35][n:36]2.Br[c:25]1[cH:26][c:27]([C:28]([NH2:29])=[O:30])[cH:31][o:32]1>>[CH3:1][C:2]([CH3:... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnc(N(C(=O)OC(C)(C)C)c2ccc(N3CCOCC3)cc2)c2ncnn12.NC(=O)c1coc(Br)c1 | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2cc(C(N)=O)co2)n2ncnc12.N | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CN(C)C=O | C-C Coupling | Stille reaction_aryl | 2d93a19b76dcf287bebe9ba413007f5f606bbf0e5afcd12afd99e2d0ec809644 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1coc(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c3ncnn23)c1 | Br-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4](-[C:5](-[N;D1;H2:6])=[O;D1;H0:7]):[c:8]:1.C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:9]1:[c:10]:[#7;a:11]:[c:12]:[c:13]2:[#7;a:14]:[c:15]:[#7;a:16]:[#7;a:17]:2:1>>[N;D1;H2:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[c:8]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9]2:[c:10]:[#7;a:11]:[c:12]:[c... | 65.6 | [{"value": 33.0, "product": "C(C)(C)(C)OC(N(C1=CC=C(C=C1)N1CCOCC1)C=1C=2N(C(=CN1)C=1OC=C(C1)C(N)=O)N=CN2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.6, "product": "C(C)(C)(C)OC(N(C1=CC=C(C=C1)N1CCOCC1)C=1C=2N(C(=CN1)C=1OC=C(C1)C(N)=O)N=CN2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | This compound may be prepared using methods as described for Compound 35, step 3 using (4-morpholin-4-yl-phenyl)-(5-tributylstannanyl-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-carbamic acid tert-butyl ester (137 mg, 0.199 mmol), 5-bromo-furan-3-carboxamide (76 mg, 0.4 mmol) and Pd(PPh3)4 (23 mg, 0.020 mmol) in DMF (1 mL). Pu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1cn2ncnc2cn1.c1ccoc1 | c1ccoc1.c1cn2ncnc2cn1 | c1ccccc1.C1COCC[NH]1.c1ccoc1.c1cn2ncnc2cn1 | HBr.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C)C=O | null | null | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnc(N(C(=O)OC(C)(C)C)c2ccc(N3CCOCC3)cc2)c2ncnn12.NC(=O)c1coc(Br)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C)C=O>CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b9266df4202d4b82be65878f09012599 | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2cc(C(N)=O)co2)n2ncnc12>>NC(=O)c1coc(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c3ncnn23)c1 | C(C)(C)(C)OC(N(C1=CC=C(C=C1)N1CCOCC1)C=1C=2N(C(=CN1)C=1OC=C(C1)C(N)=O)N=CN2)=O.C(=O)([O-])[O-].[Na+].[Na+]>>O1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C1=CC(=CO1)C(=O)N)N=CN2 | CC(C)(C)OC(=O)[N:12]([c:11]1[n:10][cH:9][c:8](-[c:7]2[o:6][cH:5][c:4]([C:2]([NH2:1])=[O:3])[cH:30]2)[n:29]2[c:25]1[n:26][cH:27][n:28]2)[c:13]1[cH:14][cH:15][c:16]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[cH:23][cH:24]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][o:6][c:7](-[c:8]2[cH:9][n:10][c:11]([NH:12][c:13]3[cH:14][cH... | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2cc(C(N)=O)co2)n2ncnc12 | NC(=O)c1coc(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c3ncnn23)c1 | null | C(=O)(C(F)(F)F)O | C(Cl)Cl | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1coc(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c3ncnn23)c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:2:1)-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:2:1):[c:13] | null | [] | null | null | null | null | A solution of [5-(4-carbamoyl-furan-2-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester (33 mg, 0.065 mmol) in a mixture 1:1 DCM:TFA (2 mL) (2 drops of water) is stirred at room temperature for 2 hours. After addition of sat. Na2CO3, a precipitate is formed, collected by f... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccoc1.c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | HO- | C(=O)(C(F)(F)F)O.C(Cl)Cl | null | null | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2cc(C(N)=O)co2)n2ncnc12>C(=O)(C(F)(F)F)O.C(Cl)Cl>NC(=O)c1coc(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c3ncnn23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e6d1cc21a2374b188d7985459089b206 | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>>N.O=C1NCc2cc(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)ccc21 | CC1(OB(OC1(C)C)C=1C=C2CNC(C2=CC1)=O)C.BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2.CC1(OB(OC1(C)C)C=1C=C2CNC(C2=CC1)=O)C.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2>>N.O1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C3CNC(C3=CC1)=O)N=CN2 | Br[c:9]1[cH:10][n:11][c:12]([NH:13][c:14]2[cH:15][cH:16][c:17]([N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[cH:24][cH:25]2)[c:26]2[n:27][cH:28][n:29][n:30]12.CC1(C)OB([c:8]2[cH:7][c:6]3[c:33]([cH:32][cH:31]2)[C:3](=[O:2])[NH:4][CH2:5]3)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(=O)[NH2:1])c4)n4ncnc34)cc2)CC1>>[NH3:1].[O:2... | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1 | N.O=C1NCc2cc(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)ccc21 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+] | C-C Coupling | OtherReaction | d96e7a493e1619b343e6902e2f3e9ceea3531a747b8fbd8e81a720c753a845f2 | 96e5f3628c1bd4659dd3e9821904115decf673d0e8e42bb7900b7f521b084c51 | O=C1NCc2cc(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)ccc21 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-O-C-1(-C)-C.C-N1-C-C-N(-c2:c:c:c(-N-c3:n:c:c(-c4:c:s:c(-C(=O)-[NH2;D1;+0:15]):c:4):n4:n:c:n:c:3:4):c:c:2)-C-C-1>>[NH3;D0;+0:15].[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:... | 79 | [{"value": 79.0, "product": "O1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C3CNC(C3=CC1)=O)N=CN2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4 using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(4-morpholin-4-yl-phenyl)-amine (1.0 g, 2.67 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one (see description for Compound 79) (1.03 g, 4.01 mmol) and Pd(... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amide.Secondary amine.Tertiary amine.Tertiary amine.Boronic ester | null | c1cn2ncnc2cn1.B1OCCO1.c1ccc2c(c1)CNC2.C1CNCCN1.c1ccccc1.c1ccsc1.c1cn2ncnc2cn1 | c1ccc2c(c1)CNC2.c1cn2ncnc2cn1 | c1ccc2c(c1)CNC2.c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+] | null | null | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(=O)([O-])[O-... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2462972170de4c979b2ad2ad40df4acf | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2coc(C(N)=O)c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>>N.NC(=O)c1cc(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c3ncnn23)co1 | CC1(OB(OC1(C)C)C=1C=C(OC1)C(=O)N)C.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.C(=O)([O-])[O-].[Na+].[Na+].BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2>>N.O1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(OC1)C(=O)N)N=CN2 | Br[c:8]1[cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][c:16]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[cH:23][cH:24]2)[c:25]2[n:26][cH:27][n:28][n:29]12.CC1(C)OB([c:7]2[cH:6][c:5]([C:3]([NH2:2])=[O:4])[o:31][cH:30]2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(=O)[NH2:1])c4)n4ncnc34)cc2)CC1>>[NH3:1].[NH2:2][C:3](=[O:4])... | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2coc(C(N)=O)c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1 | N.NC(=O)c1cc(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c3ncnn23)co1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1 | C-C Coupling | OtherReaction | 5cb7909cd8a8fb68256336e464d1363240b5ce9f1a1aa9f9849dc58e4e9eb2b6 | 96e5f3628c1bd4659dd3e9821904115decf673d0e8e42bb7900b7f521b084c51 | c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3ccoc3)n2n1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10]2:[c:11]:[#8;a:12]:[c:13](-[C:14](-[N;D1;H2:15])=[O;D1;H0:16]):[c:17]:2)-O-C-1(-C)-C.C-N1-C-C-N(-c2:c:c:c(-N-c3:n:c:c(-c4:c:s:c(-C(=O)-[NH2;D1;+0:18]):c:4):n4:n:c:n:c:3:4):c:c:2)-C-C-1>>[N;D1;H2:15]-[C:14](=... | 65 | [{"value": 65.0, "product": "O1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(OC1)C(=O)N)N=CN2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4, using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(4-morpholin-4-yl-phenyl)-amine (78 mg, 0.16 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-furan-2-carboxylic acid amide (100 mg, 0.34 mmol), and Pd(PPh3)4 (60 mg, 0.052 mmol) in... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amide.Secondary amine.Tertiary amine.Tertiary amine.Boronic ester | null | c1cn2ncnc2cn1.B1OCCO1.c1ccoc1.C1CNCCN1.c1ccccc1.c1ccsc1.c1cn2ncnc2cn1 | c1ccoc1.c1cn2ncnc2cn1 | c1ccoc1.c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1 | null | null | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2coc(C(N)=O)c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1>N.NC(=O)c1cc(-c2... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4dc67b9fd0074c14b6e5e61824caa6be | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(Br)n2ncnc12.CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC>>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnc(N(C(=O)OC(C)(C)C)c2ccc(N3CCOCC3)cc2)c2ncnn12 | C(C)(C)(C)OC(N(C1=CC=C(C=C1)N1CCOCC1)C=1C=2N(C(=CN1)Br)N=CN2)=O.C(C)(C)[Mg]Cl.C(CCC)[Sn](CCCC)(CCCC)Cl>>C(C)(C)(C)OC(N(C=1C=2N(C(=CN1)[Sn](CCCC)(CCCC)CCCC)N=CN2)C2=CC=C(C=C2)N2CCOCC2)=O | Br[c:14]1[cH:15][n:16][c:17]([N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[c:26]2[cH:27][cH:28][c:29]([N:30]3[CH2:31][CH2:32][O:33][CH2:34][CH2:35]3)[cH:36][cH:37]2)[c:38]2[n:39][cH:40][n:41][n:42]12.[Cl][Sn:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13]... | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(Br)n2ncnc12.CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnc(N(C(=O)OC(C)(C)C)c2ccc(N3CCOCC3)cc2)c2ncnn12 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 858564ed3656a34d5d3476ad96880ed87dc5473e1498305aa6913cc5a6520b94 | d9bf9bd3fc00efb5d713d9ac7f168986c2c94f1f455d32bdc9901567c1014c76 | c1cn2ncnc2c(Nc2ccc(N3CCOCC3)cc2)n1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.[C:10]-[C:11]-[Sn;H0;D4;+0:12](-[Cl])(-[C:13]-[C:14])-[C:15]-[C:16]>>[C:10]-[C:11]-[Sn;H0;D4;+0:12](-[C:13]-[C:14])(-[C:15]-[C:16])-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1 | null | [] | null | null | 5 | MINUTE | To a cooled (−78° C.) solution of (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester (370 mg, 0.78 mmol) in THF (12 mL), are added 2M isopropylmagnesium chloride in THF (0.78 mL, 1.56 mmol), and after 5 minutes stirring, tributyltin chloride (0.42, 1.56 mmol) is added.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | Tin | c1cn2ncnc2cn1 | c1cn2ncnc2cn1 | c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | Br- | C1CCOC1 | null | 0.083333 | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(Br)n2ncnc12.CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC>C1CCOC1>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnc(N(C(=O)OC(C)(C)C)c2ccc(N3CCOCC3)cc2)c2ncnn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-67395b4e30f3477f8a384fb661774435 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnc(N(C(=O)OC(C)(C)C)c2ccc(N3CCOCC3)cc2)c2ncnn12.O=C1NCCc2cc(Br)ccc21>>CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2ccc3c(c2)CCNC3=O)n2ncnc12 | C(C)(C)(C)OC(N(C=1C=2N(C(=CN1)[Sn](CCCC)(CCCC)CCCC)N=CN2)C2=CC=C(C=C2)N2CCOCC2)=O.BrC=1C=C2CCNC(C2=CC1)=O>>C(C)(C)(C)OC(N(C=1C=2N(C(=CN1)C=1C=C3CCNC(C3=CC1)=O)N=CN2)C2=CC=C(C=C2)N2CCOCC2)=O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:24]1[cH:23][n:22][c:21]([N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:9]2[cH:10][cH:11][c:12]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[cH:19][cH:20]2)[c:40]2[n:36]1[n:37][cH:38][n:39]2.Br[c:25]1[cH:26][cH:27][c:28]2[c:29]([cH:30]1)[CH2:31][CH2:32][NH:33][C:34]2=[O:3... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnc(N(C(=O)OC(C)(C)C)c2ccc(N3CCOCC3)cc2)c2ncnn12.O=C1NCCc2cc(Br)ccc21 | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2ccc3c(c2)CCNC3=O)n2ncnc12 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CN(C)C=O | C-C Coupling | Stille reaction_aryl | aec2e584c41d2913f710da02512f5af7edead4672b622f92cfa7bacdc4552ce1 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | O=C1NCCc2cc(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)ccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[c:9]:[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[#7;a:14]:2:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[c:9]:[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[#7;a:14]:2:1):[c:4]:[c:5] | 37 | [{"value": 37.0, "product": "C(C)(C)(C)OC(N(C=1C=2N(C(=CN1)C=1C=C3CCNC(C3=CC1)=O)N=CN2)C2=CC=C(C=C2)N2CCOCC2)=O", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 8 | HOUR | To a degassed solution of (4-morpholin-4-yl-phenyl)-(5-tributylstannanyl-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-carbamic acid tert-butyl ester (100 mg, 0.15 mmol) and 6-bromo-3,4-dihydro-2H-isoquinolin-1-one in DMF (1 mL) is added tetrakis(triphenylphosphine)palladium(0) (17 mg, 0.015 mmol) and the reaction mixture is sti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1cn2ncnc2cn1.c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2.c1cn2ncnc2cn1 | c1ccccc1.C1COCC[NH]1.c1ccc2c(c1)CCNC2.c1cn2ncnc2cn1 | HBr.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C)C=O | 90 | 8 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1cnc(N(C(=O)OC(C)(C)C)c2ccc(N3CCOCC3)cc2)c2ncnn12.O=C1NCCc2cc(Br)ccc21>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C)C=O>CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7938c3edbdc54f608874a20b6cd31716 | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2ccc3c(c2)CCNC3=O)n2ncnc12>>O=C1NCCc2cc(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)ccc21 | C(C)(C)(C)OC(N(C=1C=2N(C(=CN1)C=1C=C3CCNC(C3=CC1)=O)N=CN2)C2=CC=C(C=C2)N2CCOCC2)=O.C(=O)(C(F)(F)F)O>>N1(CCOCC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C3CCNC(C3=CC1)=O)N=CN2 | CC(C)(C)OC(=O)[N:13]([c:12]1[n:11][cH:10][c:9](-[c:8]2[cH:7][c:6]3[c:33]([cH:32][cH:31]2)[C:2](=[O:1])[NH:3][CH2:4][CH2:5]3)[n:30]2[c:26]1[n:27][cH:28][n:29]2)[c:14]1[cH:15][cH:16][c:17]([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[cH:24][cH:25]1>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][c:6]2[cH:7][c:8](-[c:9]3[cH:10][n:11... | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2ccc3c(c2)CCNC3=O)n2ncnc12 | O=C1NCCc2cc(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)ccc21 | null | C(Cl)Cl | null | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C1NCCc2cc(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)ccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:2:1)-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:2:1):[c:13] | null | [] | null | null | null | null | A solution of (4-morpholin-4-yl-phenyl)-[5-(1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-carbamic acid tert-butyl ester (30 mg, 0.055 mmol) in a 1:1 mixture of TFA:DCM (1 drop of H2O), is stirred at room temperature for 2 hours. The solvent is removed in vacuo and the residue partition... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccc2c(c1)CCNC2.c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | HO- | C(Cl)Cl | null | null | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2ccc3c(c2)CCNC3=O)n2ncnc12>C(Cl)Cl>O=C1NCCc2cc(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-53d975bc652a4e4b92204764fa281685 | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cn2)CC1.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>>CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccc5c(c4)CNC5=O)n4ncnc34)cc2)CC1.N | CC1(OB(OC1(C)C)C=1C=C2CNC(C2=CC1)=O)C.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.BrC1=CN=C(C=2N1N=CN2)NC=2C=NC(=CC2)N2CCN(CC2)C(C)C>>N.C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C3CNC(C3=CC1)=O)N=CN2 | Br[c:16]1[cH:15][n:14][c:13]([NH:12][c:11]2[cH:10][cH:9][c:8]([N:7]3[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:35][CH2:34]3)n[cH:32]2)[c:31]2[n:27]1[n:28][cH:29][n:30]2.CC1(C)OB([c:17]2[cH:18][cH:19][c:20]3[c:21]([cH:22]2)[CH2:23][NH:24][C:25]3=[O:26])OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(=O)[NH2:36])c4)n4ncnc34)c[... | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cn2)CC1.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1 | CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccc5c(c4)CNC5=O)n4ncnc34)cc2)CC1.N | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+] | C-C Coupling | OtherReaction | a2d6d816881570f37f8a1f9df37f734d7c5a33d1c9b1b2ab51414b770206e0a5 | 96e5f3628c1bd4659dd3e9821904115decf673d0e8e42bb7900b7f521b084c51 | O=C1NCc2cc(-c3cnc(Nc4ccc(N5CCNCC5)cc4)c4ncnn34)ccc21 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](-[#7:5]-[c:6]2:[c:7]:[c:8]:[c;H0;D3;+0:9](-[#7:10](-[C:11])-[C:12]):n:[cH;D2;+0:13]:2):[c:14]2:[#7;a:15]:[c:16]:[#7;a:17]:[#7;a:18]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:19](:[c:20]:[c:21]):[c:22]:[c:23])-O-C-1(-C)-C.C-N1-C-C-N(-c2:[cH;D2;+0:24]:c:c(-N-c3:n:c:c(-c4:c:s:c(-C(=O)-[NH2;D1;+... | 53 | [{"value": 53.0, "product": "C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C3CNC(C3=CC1)=O)N=CN2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4 using 5-bromo-N-(6-(4-isopropylpiperazin-1-yl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine (0.6 g, 1.44 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one (0.56 g, 2.16 mmol) and Pd(PPh3)4 (0.416 g, 0.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amide.Secondary amine.Tertiary amine.Tertiary amine.Boronic ester | null | c1ccncc1.c1cn2ncnc2cn1.B1OCCO1.c1ccc2c(c1)CNC2.C1CNCCN1.c1ccccc1.c1ccsc1.c1cn2ncnc2cn1 | c1ccccc1.c1ccc2c(c1)CNC2.c1cn2ncnc2cn1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CNC2.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+] | null | null | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cn2)CC1.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(=O)([... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-15d03c4c681e44989f868d3ab7184f0b | O=Cc1cc([N+](=O)[O-])ccc1N1CCOCC1>>O=[N+]([O-])c1ccc(N2CCOCC2)c(CO)c1 | N1(CCOCC1)C1=C(C=O)C=C(C=C1)[N+](=O)[O-].[BH4-].[Na+]>>N1(CCOCC1)C1=C(C=C(C=C1)[N+](=O)[O-])CO | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[c:14]([CH:15]=[O:16])[cH:17]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[c:14]([CH2:15][OH:16])[cH:17]1 | O=Cc1cc([N+](=O)[O-])ccc1N1CCOCC1 | O=[N+]([O-])c1ccc(N2CCOCC2)c(CO)c1 | null | null | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(N2CCOCC2)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 107.7 | [{"value": 107.7, "product": "N1(CCOCC1)C1=C(C=C(C=C1)[N+](=O)[O-])CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a cooled (0° C.) solution of 2-morpholin-4-yl-5-nitro-benzaldehyde (0.8 g, 3.39 mmol) in MeOH (5 mL) is added NaBH4 (0.125 g, 3.39 mmol) and the reaction mixture is stirred at room temperature for 3 hours. After quenching the reaction with water, the solvent is removed in vacuo and the residue dissolved in ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1.C1COCC[NH]1 | null | CO | null | 3 | O=Cc1cc([N+](=O)[O-])ccc1N1CCOCC1>CO>O=[N+]([O-])c1ccc(N2CCOCC2)c(CO)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-75019e1e3bef47e7aae77212098bbedc | O=[N+]([O-])c1ccc(N2CCOCC2)c(CO)c1>>Nc1ccc(N2CCOCC2)c(CO)c1 | N1(CCOCC1)C1=C(C=C(C=C1)[N+](=O)[O-])CO>>NC=1C=CC(=C(C1)CO)N1CCOCC1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[c:12]([CH2:13][OH:14])[cH:15]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)[c:12]([CH2:13][OH:14])[cH:15]1 | O=[N+]([O-])c1ccc(N2CCOCC2)c(CO)c1 | Nc1ccc(N2CCOCC2)c(CO)c1 | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCOCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 84.2 | [{"value": 83.0, "product": "NC=1C=CC(=C(C1)CO)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.2, "product": "NC=1C=CC(=C(C1)CO)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of (2-morpholin-4-yl-5-nitro-phenyl)-methanol (870 mg) in ethanol (40 mL) palladium hydroxide (87 mg) is added and the mixture is stirred in a Parr-apparatus under hydrogen pressure (10 bars) for 4 hours. The reaction mixture is filtrated over Celite 521, washed with ethanol and concentrated in vacuo to g... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1COCC[NH]1 | Other | C(C)O | null | 4 | O=[N+]([O-])c1ccc(N2CCOCC2)c(CO)c1>C(C)O>Nc1ccc(N2CCOCC2)c(CO)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c3d56357835e4c608cff369d74c8512d | Brc1ncc(Br)n2ncnc12.CC(C)(C)[SiH2]OC(C)(C)c1cc(N)ccc1N1CCOCC1>>CC(C)(C)[SiH2]OC(C)(C)c1cc(Nc2ncc(Br)n3ncnc23)ccc1N1CCOCC1 | BrC1=CN=C(C=2N1N=CN2)Br.C(C)(C)(C)[SiH2]OC(C=1C=C(C=CC1N1CCOCC1)N)(C)C.C(C)N(C(C)C)C(C)C>>BrC1=CN=C(C=2N1N=CN2)NC2=CC(=C(C=C2)N2CCOCC2)C(O[SiH2]C(C)(C)C)(C)C | Br[c:14]1[n:15][cH:16][c:17]([Br:18])[n:19]2[n:20][cH:21][n:22][c:23]12.[CH3:1][C:2]([CH3:3])([CH3:4])[SiH2:5][O:6][C:7]([CH3:8])([CH3:9])[c:10]1[cH:11][c:12]([NH2:13])[cH:24][cH:25][c:26]1[N:27]1[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[SiH2:5][O:6][C:7]([CH3:8])([CH3:9])[c:10]1[cH:11][c:... | Brc1ncc(Br)n2ncnc12.CC(C)(C)[SiH2]OC(C)(C)c1cc(N)ccc1N1CCOCC1 | CC(C)(C)[SiH2]OC(C)(C)c1cc(Nc2ncc(Br)n3ncnc23)ccc1N1CCOCC1 | null | null | CC(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | aecfb0ede2c5d7901fea69101287828edf21f7a6e48b6ff83fe43de0688f1ef1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn2ncnc2c(Nc2ccc(N3CCOCC3)cc2)n1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 46 | [{"value": 46.0, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC(=C(C=C2)N2CCOCC2)C(O[SiH2]C(C)(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.7, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC(=C(C=C2)N2CCOCC2)C(O[SiH2]C(C)(C)C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (0.391 g, 1.41 mmol), 3-(tert-butyl-dimethyl-silanyloxymethyl)-4-morpholin-4-yl-phenylamine (0.5 g, 1.55 mmol) and N-ethyldiisopropyl-amine (0.27 mL, 1.55 mmol) is heated at 90° C. in 2-propanol (10 mL) for 8 hours. The reaction mixture is evaporated to dryness an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cn2ncnc2cn1 | c1cn2ncnc2cn1 | c1ccccc1.c1cn2ncnc2cn1.C1COCC[NH]1 | HBr | CC(C)O | null | null | Brc1ncc(Br)n2ncnc12.CC(C)(C)[SiH2]OC(C)(C)c1cc(N)ccc1N1CCOCC1>CC(C)O>CC(C)(C)[SiH2]OC(C)(C)c1cc(Nc2ncc(Br)n3ncnc23)ccc1N1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-84ec7188b62045c095ea3d6a40c8ef00 | CC1(C)OB(c2cn[nH]c2)OC1(C)C.OCc1cc(Nc2ncc(Br)n3ncnc23)ccc1N1CCOCC1>>OCc1cc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)ccc1N1CCOCC1 | CC1(OB(OC1(C)C)C=1C=NNC1)C.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.BrC1=CN=C(C=2N1N=CN2)NC=2C=CC(=C(C2)CO)N2CCOCC2>>N1N=CC(=C1)C1=CN=C(C=2N1N=CN2)NC=2C=CC(=C(C2)CO)N2CCOCC2 | CC1(C)OB([c:11]2[cH:12][n:13][nH:14][cH:15]2)OC1(C)C.Br[c:10]1[cH:9][n:8][c:7]([NH:6][c:5]2[cH:4][c:3]([CH2:2][OH:1])[c:23]([N:24]3[CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[cH:22][cH:21]2)[c:20]2[n:16]1[n:17][cH:18][n:19]2>>[OH:1][CH2:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][n:13][nH:14][cH:15]3... | CC1(C)OB(c2cn[nH]c2)OC1(C)C.OCc1cc(Nc2ncc(Br)n3ncnc23)ccc1N1CCOCC1 | OCc1cc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)ccc1N1CCOCC1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+] | C-C Coupling | Suzuki coupling with boronic esters | 3b077e58a8068174133a7eecad35957570f9290725408c31a955826b02d2e470 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3cn[nH]c3)n2n1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[#7;a:13]:[c:14]:2)-O-C-1(-C)-C>>[#7;a:12]1:[#7;a:13]:[c:14]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[#7;a:3]:[c:4]:[c:5]3:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:3:2):[c:11]:1 | 12 | [{"value": 12.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4 using [5-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-2-morpholin-4-yl-phenyl]-methanol (85 mg, 0.21 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxa-borolan-2-yl)-1H-pyrazole (81 mg, 0.42 mmol) and Pd(PPh3)4 (60 mg, 0.052 mmol) in 1.5M Na2C... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1cn[nH]c1.c1cn2ncnc2cn1 | c1cn[nH]c1.c1cn2ncnc2cn1 | c1ccccc1.c1cn[nH]c1.c1cn2ncnc2cn1.C1COCC[NH]1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+] | null | null | CC1(C)OB(c2cn[nH]c2)OC1(C)C.OCc1cc(Nc2ncc(Br)n3ncnc23)ccc1N1CCOCC1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>OCc1cc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)ccc1N1CCOC... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a066fb1722274b7c9b1147bd17cfb52b | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2csc3ccccc23)OC1(C)C>>c1ccc2c(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)csc2c1 | BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2.CC1(OB(OC1(C)C)C=1C2=C(SC1)C=CC=C2)C>>S1C2=C(C(=C1)C1=CN=C(C=3N1N=CN3)NC3=CC=C(C=C3)N3CCOCC3)C=CC=C2 | Br[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][cH:13][c:14]([N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)[cH:21][cH:22]2)[c:23]2[n:24][cH:25][n:26][n:27]12.CC1(C)OB([c:5]2[c:4]3[cH:3][cH:2][cH:1][cH:31][c:30]3[s:29][cH:28]2)OC1(C)C>>[cH:1]1[cH:2][cH:3][c:4]2[c:5](-[c:6]3[cH:7][n:8][c:9]([NH:10][c:11]4[cH:12][cH:13][c... | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2csc3ccccc23)OC1(C)C | c1ccc2c(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)csc2c1 | null | null | null | C-C Coupling | Suzuki coupling with boronic esters | b93680bb40a0e9e2c1d4273451dc351a647432fa5a851c052732cedf7ebf5184 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc2c(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)csc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10]2:[c:11]:[#16;a:12]:[c:13](:[c:14]):[c:15]:2:[c:16])-O-C-1(-C)-C>>[c:14]:[c:13]1:[#16;a:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[#7;a:3]:[c:4]:[c:5]3:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:3:2):[c:15]:1:... | null | [] | null | null | null | null | This compound may be prepared using methods as described for Compound 120, using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(4-morpholin-4-ylphenyl)amine and 4,4,5,5-tetramethyl-2-benzo[b]thiophen-3-yl-[1,3,2]dioxaborolane in step 4. LCMS: Rt 0.84 min (95%), m/z (ESI) 402 (M+H)+.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1cn2ncnc2cn1.B1OCCO1.c1ccc2sccc2c1 | c1cn2ncnc2cn1.c1ccc2sccc2c1 | c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1.c1ccc2sccc2c1 | HBr.B | null | null | null | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2csc3ccccc23)OC1(C)C>>c1ccc2c(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)csc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-672580c563064a18b763e72fd568a784 | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2ccsc2)OC1(C)C>>c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3ccsc3)n2n1 | BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2.CC1(OB(OC1(C)C)C1=CSC=C1)C>>N1(CCOCC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C1=CSC=C1)N=CN2 | Br[c:20]1[cH:19][n:18][c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[cH:16][cH:17]2)[c:3]2[n:2][cH:1][n:27][n:26]21.CC1(C)OB([c:21]2[cH:22][cH:23][s:24][cH:25]2)OC1(C)C>>[cH:1]1[n:2][c:3]2[c:4]([NH:5][c:6]3[cH:7][cH:8][c:9]([N:10]4[CH2:11][CH2:12][O:13][CH2:14][CH2:15]4)[cH:16][cH:1... | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2ccsc2)OC1(C)C | c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3ccsc3)n2n1 | null | null | null | C-C Coupling | Suzuki coupling with boronic esters | 791f73e9e8c7588b7846191c9fedfcf6e2595c90e46d286b94f30804a763a2ec | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3ccsc3)n2n1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10]2:[c:11]:[c:12]:[#16;a:13]:[c:14]:2)-O-C-1(-C)-C>>[#16;a:13]1:[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[#7;a:3]:[c:4]:[c:5]3:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:3:2):[c:14]:1 | null | [] | null | null | null | null | This compound may be prepared using methods as described for Compound 120, using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(4-morpholin-4-ylphenyl)amine and 4,4,5,5-tetramethyl-2-thiophen-3-yl-[1,3,2]dioxaborolane in step 4. LCMS: Rt 1.19 min (95%), m/z (ESI) 379 (M+H)+.
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1cn2ncnc2cn1.B1OCCO1.c1ccsc1 | c1cn2ncnc2cn1.c1ccsc1 | c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1.c1ccsc1 | HBr.B | null | null | null | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2ccsc2)OC1(C)C>>c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3ccsc3)n2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-396a2a55c1a547f69c1569621ac6bcca | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CCc1c(B2OC(C)(C)C(C)(C)O2)cnn1C1CCCCO1>>CCc1[nH]ncc1-c1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12 | CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.C(=O)([O-])[O-].[Na+].[Na+].C(C)C1=C(C=NN1C1OCCCC1)B1OC(C(O1)(C)C)(C)C.C(C)C1=NN(C=C1B1OC(C(O1)(C)C)(C)C)C1OCCCC1.BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2>>C(C)C1=C(C=NN1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2 | Br[c:8]1[cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][c:16]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[cH:23][cH:24]2)[c:25]2[n:26][cH:27][n:28][n:29]12.CC1(C)OB([c:7]2[c:3]([CH2:2][CH3:1])[n:4](C3CCCCO3)[n:5][cH:6]2)OC1(C)C>>[CH3:1][CH2:2][c:3]1[nH:4][n:5][cH:6][c:7]1-[c:8]1[cH:9][n:10][c:11]([NH:12][c:13]2[cH:... | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CCc1c(B2OC(C)(C)C(C)(C)O2)cnn1C1CCCCO1 | CCc1[nH]ncc1-c1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1 | C-C Coupling | OtherReaction | 5b250e4178d9f7ec19c8f75544930eff90278ccea3ebf86411859b7895245136 | 664bb683b7d04c49fddf80239ea7ce0c421519efd3bdfdeb0820befa736cf196 | c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3cn[nH]c3)n2n1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[n;H0;D3;+0:13](-C3-C-C-C-C-O-3):[c:14]:2-[C:15])-O-C-1(-C)-C>>[C:15]-[c:14]1:[nH;D2;+0:13]:[#7;a:12]:[c:11]:[c;H0;D3;+0:10]:1-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#... | null | [] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4 using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(4-morpholin-4-yl-phenyl)-amine (0.032 g, 0.085 mmol), 5-ethyl-1-(tetrahydro-pyran-2-yl)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole and 3-ethyl-1-(tetrahydro-pyran-2-yl)-4... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Boronic ester | null | c1cn2ncnc2cn1.B1OCCO1.c1c[nH]nc1.C1CCOCC1 | c1cn[nH]c1.c1cn2ncnc2cn1 | c1cn[nH]c1.c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1 | null | null | Brc1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12.CCc1c(B2OC(C)(C)C(C)(C)O2)cnn1C1CCCCO1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1>CCc1[nH]ncc1-c1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bec95c032eb84b4ca0472d157d283fe2 | CCc1nn(C2CCCCO2)cc1-c1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12>>CCc1[nH]ncc1-c1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12 | C(C)C1=C(C=NN1C1OCCCC1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2.C(C)C1=NN(C=C1C1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2)C2OCCCC2.Cl>>C(C)C1=C(C=NN1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2 | C1CCC([n:5]2[n:4][c:3]([CH2:2][CH3:1])[c:7](-[c:8]3[cH:9][n:10][c:11]([NH:12][c:13]4[cH:14][cH:15][c:16]([N:17]5[CH2:18][CH2:19][O:20][CH2:21][CH2:22]5)[cH:23][cH:24]4)[c:25]4[n:26][cH:27][n:28][n:29]34)[cH:6]2)OC1>>[CH3:1][CH2:2][c:3]1[nH:4][n:5][cH:6][c:7]1-[c:8]1[cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][c:16](... | CCc1nn(C2CCCCO2)cc1-c1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12 | CCc1[nH]ncc1-c1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12 | null | null | CO | Reduction | OtherReaction | 961a72974526db3621ed05df5cf40c54af32f87acb02ef9960ca6098e4d5b0ab | 84394d34c591024a84d9393eb3e8adb8ada5a6225c3abafc4dae9aedd4568be4 | c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3cn[nH]c3)n2n1 | [C:1]-[c:2]1:[c:3]:[c:4]:[n;H0;D3;+0:5](-C2-C-C-C-C-O-2):[n;H0;D2;+0:6]:1>>[C:1]-[c:2]1:[c:3]:[c:4]:[n;H0;D2;+0:5]:[nH;D2;+0:6]:1 | 17 | [{"value": 17.0, "product": "C(C)C1=C(C=NN1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of {5-[5-ethyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyrazin-8-yl}-(4-morpholin-4-yl-phenyl)-amine and {5-[3-ethyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyrazin-8-yl}-(4-morpholin-4-yl-phenyl)-amine (40 mg, 0.077 mmol) and conc. HCl (0.3 mL) in MeOH (10 m... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | C1CCOCC1.c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | HO- | CO | null | null | CCc1nn(C2CCCCO2)cc1-c1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12>CO>CCc1[nH]ncc1-c1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4c857d3926b7406ebf93ef0b47bf93d2 | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(Br)n2ncnc12.CC1(C)OB(c2ccc3c(c2)S(=O)(=O)NC3=O)OC1(C)C>>CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2ccc3c(c2)S(=O)(=O)NC3=O)n2ncnc12 | C(=O)([O-])[O-].[Na+].[Na+].CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.C(C)(C)(C)OC(N(C1=CC=C(C=C1)N1CCOCC1)C=1C=2N(C(=CN1)Br)N=CN2)=O.O=S1(NC(C2=C1C=C(C=C2)B2OC(C(O2)(C)C)(C)C)=O)=O>>C(C)(C)(C)OC(N(C=1C=2N(C(=CN1)C1=CC3=C(C(NS3(=O)=O)=O)C=C1)N=CN2)C2=CC=C(C=C2)N2CCOCC2)=O | Br[c:24]1[cH:23][n:22][c:21]([N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:9]2[cH:10][cH:11][c:12]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[cH:19][cH:20]2)[c:41]2[n:37]1[n:38][cH:39][n:40]2.CC1(C)OB([c:25]2[cH:26][cH:27][c:28]3[c:29]([cH:30]2)[S:31](=[O:32])(=[O:33])[NH:34][C:35]3=[O:36])OC1(C)C>>[CH... | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(Br)n2ncnc12.CC1(C)OB(c2ccc3c(c2)S(=O)(=O)NC3=O)OC1(C)C | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2ccc3c(c2)S(=O)(=O)NC3=O)n2ncnc12 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic esters | a4e44fbcfebb2e9ed792a442fe98ba6e4e5c8972cb98fc27d617b9afb5655b91 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | O=C1NS(=O)(=O)c2cc(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)ccc21 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]-[#16:15])-O-C-1(-C)-C>>[#16:15]-[c:14]:[c:13]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1):[c:11]:[c:12] | 44 | [{"value": 44.0, "product": "C(C)(C)(C)OC(N(C=1C=2N(C(=CN1)C1=CC3=C(C(NS3(=O)=O)=O)C=C1)N=CN2)C2=CC=C(C=C2)N2CCOCC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.8, "product": "C(C)(C)(C)OC(N(C=1C=2N(C(=CN1)C1=CC3=C(C(NS3(=O)=O)=O)C=C1)N=CN2)C2=CC=C(C=C2)N2CCOCC2)=O", "details": "CALCULATEDPERCENTY... | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4 using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester (170 mg, 0.36 mmol), 1,1-dioxo-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2-dihydro-1λ6-benzo[d]isothiazol-3-one (374 mg, 0.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1cn2ncnc2cn1.B1OCCO1.c1ccc2c(c1)CNS2 | c1ccc2c(c1)CNS2.c1cn2ncnc2cn1 | c1ccccc1.C1COCC[NH]1.c1ccc2c(c1)CNS2.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1 | null | null | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(Br)n2ncnc12.CC1(C)OB(c2ccc3c(c2)S(=O)(=O)NC3=O)OC1(C)C>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1>CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a87de850dfd4c0298869c44948ccf9e | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2ccc3c(c2)S(=O)(=O)NC3=O)n2ncnc12>>O=C1NS(=O)(=O)c2cc(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)ccc21 | C(C)(C)(C)OC(N(C=1C=2N(C(=CN1)C1=CC3=C(C(NS3(=O)=O)=O)C=C1)N=CN2)C2=CC=C(C=C2)N2CCOCC2)=O>>N1(CCOCC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C1=CC3=C(C(NS3(=O)=O)=O)C=C1)N=CN2 | CC(C)(C)OC(=O)[N:14]([c:13]1[n:12][cH:11][c:10](-[c:9]2[cH:8][c:7]3[c:34]([cH:33][cH:32]2)[C:2](=[O:1])[NH:3][S:4]3(=[O:5])=[O:6])[n:31]2[c:27]1[n:28][cH:29][n:30]2)[c:15]1[cH:16][cH:17][c:18]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[cH:25][cH:26]1>>[O:1]=[C:2]1[NH:3][S:4](=[O:5])(=[O:6])[c:7]2[cH:8][c:9](-[c:10... | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2ccc3c(c2)S(=O)(=O)NC3=O)n2ncnc12 | O=C1NS(=O)(=O)c2cc(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)ccc21 | null | null | Cl.O1CCOCC1 | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C1NS(=O)(=O)c2cc(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)ccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:2:1)-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:2:1):[c:13] | 101.7 | [{"value": 100.0, "product": "N1(CCOCC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C1=CC3=C(C(NS3(=O)=O)=O)C=C1)N=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.7, "product": "N1(CCOCC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C1=CC3=C(C(NS3(=O)=O)=O)C=C1)N=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A suspension of (4-morpholin-4-yl-phenyl)-[5-(1,1,3-trioxo-2,3-dihydro-1H-1 λ6-benzo[d]isothiazol-6-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-carbamic acid tert-butyl ester (100 mg, 0.173 mmol) in 4M HCl (2.5 mL) in dioxane is stirred at room temperature for 2 hours. The solvent is removed under vacuum and the residue is... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccc2c(c1)CNS2.c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | HO- | Cl.O1CCOCC1 | null | 2 | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2ccc3c(c2)S(=O)(=O)NC3=O)n2ncnc12>Cl.O1CCOCC1>O=C1NS(=O)(=O)c2cc(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b56b59d5fa145af9eed651afa727787 | NC(=O)c1cc(B(O)O)cs1.c1nc2c(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)ncc(-c3cn[nH]c3)n2n1>>NC(=O)c1cc(-c2cnc(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)c3ncnn23)cs1 | C1(CC1)CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=NNC1)N=CN2.NC(=O)C=1SC=C(C1)B(O)O>>C1(CC1)CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2 | OB(O)[c:6]1[cH:5][c:4]([C:2]([NH2:1])=[O:3])[s:34][cH:33]1.c1n[nH]cc1-[c:7]1[cH:8][n:9][c:10]([NH:11][c:12]2[cH:13][cH:14][c:15]([N:16]3[CH2:17][CH2:18][N:19]([CH2:20][CH:21]4[CH2:22][CH2:23]4)[CH2:24][CH2:25]3)[cH:26][cH:27]2)[c:28]2[n:29][cH:30][n:31][n:32]12>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][n:9][... | NC(=O)c1cc(B(O)O)cs1.c1nc2c(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)ncc(-c3cn[nH]c3)n2n1 | NC(=O)c1cc(-c2cnc(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)c3ncnn23)cs1 | null | null | null | C-C Coupling | OtherReaction | f3b9026c2e0fca3f66449ae83278e72e26246a4e0c9e12eb550a3525259554d6 | fb7ad422d905bdc265298a43c871eec14eab0c8cca46cc3d1bd494f2a986d765 | c1nc2c(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)ncc(-c3ccsc3)n2n1 | O-B(-O)-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4](-[C:5](-[N;D1;H2:6])=[O;D1;H0:7]):[c:8]:1.[#7;a:9]1:[c:10]:[#7;a:11]:[#7;a:12]2:[c:13]:1:[c:14]:[#7;a:15]:[c:16]:[c;H0;D3;+0:17]:2-c1:c:[nH]:n:c:1>>[N;D1;H2:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[#16;a:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:17]2:[c:16]:[#7;a:15]:[c:14]:[c:13]3:[#7;a:... | null | [] | null | null | null | null | This compound may be prepared using methods as described for Compound 46, using 2-(aminocarbonyl)thiophene-4-boronic acid. LCMS: Rt=0.93 (95%), m/z (ESI) 475 (M+H)+.
Conditions: See reaction.notes.procedure_details.
Workup: This compound may be prepared | 10.6084/m9.figshare.5104873.v1 | null | Boronic acid | null | c1ccsc1.c1cn[nH]c1.c1cn2ncnc2cn1 | c1ccsc1.c1cn2ncnc2cn1 | c1ccsc1.c1ccccc1.C1C[NH]CC[NH]1.C1CC1.c1cn2ncnc2cn1 | HO-.B | null | null | null | NC(=O)c1cc(B(O)O)cs1.c1nc2c(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)ncc(-c3cn[nH]c3)n2n1>>NC(=O)c1cc(-c2cnc(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)c3ncnn23)cs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1efc6fe587264f8aaf7606db9287f461 | Brc1cnc(Nc2ccc(N3CCN(C4CC4)CC3)cc2)c2ncnn12.c1nc2c(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)ncc(-c3cn[nH]c3)n2n1>>c1nc2c(Nc3ccc(N4CCN(C5CC5)CC4)cc3)ncc(-c3cn[nH]c3)n2n1 | C1(CC1)CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=NNC1)N=CN2.BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCN(CC2)C2CC2>>C1(CC1)N1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=NNC1)N=CN2 | Brc1cnc(Nc2ccc(N3CCN([CH:14]4[CH2:15][CH2:16]4)CC3)cc2)c2ncnn12.C1CC1C[N:13]1[CH2:12][CH2:11][N:10]([c:9]2[cH:8][cH:7][c:6]([NH:5][c:4]3[c:3]4[n:2][cH:1][n:30][n:29]4[c:23](-[c:24]4[cH:25][n:26][nH:27][cH:28]4)[cH:22][n:21]3)[cH:20][cH:19]2)[CH2:18][CH2:17]1>>[cH:1]1[n:2][c:3]2[c:4]([NH:5][c:6]3[cH:7][cH:8][c:9]([N:10]... | Brc1cnc(Nc2ccc(N3CCN(C4CC4)CC3)cc2)c2ncnn12.c1nc2c(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)ncc(-c3cn[nH]c3)n2n1 | c1nc2c(Nc3ccc(N4CCN(C5CC5)CC4)cc3)ncc(-c3cn[nH]c3)n2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | dee39114e4673f33fbc41f563b9534d440103232ec7deedb605e56fdd0259127 | 620797dd8280f68fb96af89f30cfa19ffb92b9594066c67b5bfa02ac48fff79f | c1nc2c(Nc3ccc(N4CCN(C5CC5)CC4)cc3)ncc(-c3cn[nH]c3)n2n1 | Br-c1:c:n:c(-N-c2:c:c:c(-N3-C-C-N(-[CH;D3;+0:1]4-[C:2]-[C:3]-4)-C-C-3):c:c:2):c2:n:c:n:n:1:2.C1-C-C-1-C-[N;H0;D3;+0:4]1-[C:5]-[C:6]-[#7:7]-[C:8]-[C:9]-1>>[#7:7]1-[C:6]-[C:5]-[N;H0;D3;+0:4](-[CH;D3;+0:1]2-[C:2]-[C:3]-2)-[C:9]-[C:8]-1 | null | [] | null | null | null | null | This compound may be prepared using methods as described for Compound 46, using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(4-cyclopropylpiperazin-1-yl)-phenyl]amine. LCMS: Rt=0.84 (95%), m/z (ESI) 402 (M+H)+.
Conditions: See reaction.notes.procedure_details.
Workup: This compound may be prepared | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine.Tertiary amine.Tertiary amine.Tertiary amine | Tertiary amine | c1ccccc1.C1CNCCN1.C1CC1.c1cn2ncnc2cn1.C1CC1.C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.C1CC1 | c1ccccc1.C1C[NH]CC[NH]1.C1CC1.c1cn2ncnc2cn1.c1cn[nH]c1 | HBr | null | null | null | Brc1cnc(Nc2ccc(N3CCN(C4CC4)CC3)cc2)c2ncnn12.c1nc2c(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)ncc(-c3cn[nH]c3)n2n1>>c1nc2c(Nc3ccc(N4CCN(C5CC5)CC4)cc3)ncc(-c3cn[nH]c3)n2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-458f93ff7bf64ce7b249c7fe30a69a34 | O=C(N1CCC(c2ccc([N+](=O)[O-])cc2)CC1)C(F)(F)F>>O=[N+]([O-])c1ccc(C2CCN(CC(F)(F)F)CC2)cc1 | N#N.[BH4-].[Na+].FC(C(=O)N1CCC(CC1)C1=CC=C(C=C1)[N+](=O)[O-])(F)F.II>>FC(CN1CCC(CC1)C1=CC=C(C=C1)[N+](=O)[O-])(F)F | O=[C:12]([N:11]1[CH2:10][CH2:9][CH:8]([c:7]2[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:20][cH:19]2)[CH2:18][CH2:17]1)[C:13]([F:14])([F:15])[F:16]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][N:11]([CH2:12][C:13]([F:14])([F:15])[F:16])[CH2:17][CH2:18]2)[cH:19][cH:20]1 | O=C(N1CCC(c2ccc([N+](=O)[O-])cc2)CC1)C(F)(F)F | O=[N+]([O-])c1ccc(C2CCN(CC(F)(F)F)CC2)cc1 | null | null | C1CCOC1 | Reduction | Reduction of tertiary amides to amines | f74c5a050b269ec4da3871c266f01344b7447381f47cda744f8b1e9c225ae62d | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | c1ccc(C2CCNCC2)cc1 | O=[C;H0;D3;+0:1](-[#7:2](-[C:3])-[C:4])-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]>>[C:3]-[#7:2](-[CH2;D2;+0:1]-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8])-[C:4] | null | [] | 0 | CELSIUS | null | null | A solution of 1-trifluoroacetyl-4-(4-nitrophenyl)piperidine (1.42 g, 4.7 mmol) in THF (15 mL) is stirred in 25 mL 2-necked flask fitted with a condenser and pressure-equalizing addition funnel. The system is flushed with N2, NaBH4 (210 mg, 5.6 mmol) is added and the flask is cooled to 0° C. A solution of iodine (600 mg... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | null | null | c1ccccc1.C1CC[NH]CC1 | Other | C1CCOC1 | 0 | null | O=C(N1CCC(c2ccc([N+](=O)[O-])cc2)CC1)C(F)(F)F>C1CCOC1>O=[N+]([O-])c1ccc(C2CCN(CC(F)(F)F)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ceaf160cdc434884bdc4d842b0127abb | O=[N+]([O-])c1ccc(C2CCN(CC(F)(F)F)CC2)cc1>>O=CNc1ccc(C2CCN(CC(F)(F)F)CC2)cc1 | C(=O)[O-].[NH4+].FC(CN1CCC(CC1)C1=CC=C(C=C1)[N+](=O)[O-])(F)F.C(=O)[O-].[NH4+]>>FC(CN1CCC(CC1)C1=CC=C(C=C1)NC=O)(F)F | O=[N+:3]([O-])[c:4]1[cH:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][N:11]([CH2:12][C:13]([F:14])([F:15])[F:16])[CH2:17][CH2:18]2)[cH:19][cH:20]1>>[O:1]=[CH:2][NH:3][c:4]1[cH:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][N:11]([CH2:12][C:13]([F:14])([F:15])[F:16])[CH2:17][CH2:18]2)[cH:19][cH:20]1 | O=[N+]([O-])c1ccc(C2CCN(CC(F)(F)F)CC2)cc1 | O=CNc1ccc(C2CCN(CC(F)(F)F)CC2)cc1 | null | [Pd] | CCO.CCOC(=O)C | Functional Group Interconversion | OtherReaction | 81e9c00cc56669b3382585c40a086ed7e5aaaab80bc5382ed121e4d5a293b433 | 013ea010a5fc8551154a976160b11b17bb85fae400bd37b37532ea17a3df22d8 | c1ccc(C2CCNCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[O;D1;H0:5]=[C:6]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 77.8 | [{"value": 77.8, "product": "FC(CN1CCC(CC1)C1=CC=C(C=C1)NC=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ammonium formate (1.38 g, 22 mmol) and 10% Pd/C (230 mg, 0.2 mmol) are added to a solution of 1-(2,2,2-trifluoroethyl)-4-(4-nitrophenyl)piperidine (1.26 g, 4.4 mmol) in EtOH (10 mL) and EtOAc (10 mL). The suspension is heated at reflux for 24 hours, adding further portions of ammonium formate (2 g) after 4 h and 8 h. T... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Secondary amide | null | null | c1ccccc1.C1CC[NH]CC1 | null | [Pd].CCO.CCOC(=O)C | null | null | O=[N+]([O-])c1ccc(C2CCN(CC(F)(F)F)CC2)cc1>[Pd].CCO.CCOC(=O)C>O=CNc1ccc(C2CCN(CC(F)(F)F)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a806c2c14d04eb1937fed9f0b30ef37 | O=CNc1ccc(C2CCN(CC(F)(F)F)CC2)cc1>>Nc1ccc(C2CCN(CC(F)(F)F)CC2)cc1 | FC(CN1CCC(CC1)C1=CC=C(C=C1)NC=O)(F)F.Cl>>FC(CN1CCC(CC1)C1=CC=C(C=C1)N)(F)F | O=C[NH:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][CH2:8][N:9]([CH2:10][C:11]([F:12])([F:13])[F:14])[CH2:15][CH2:16]2)[cH:17][cH:18]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][CH2:8][N:9]([CH2:10][C:11]([F:12])([F:13])[F:14])[CH2:15][CH2:16]2)[cH:17][cH:18]1 | O=CNc1ccc(C2CCN(CC(F)(F)F)CC2)cc1 | Nc1ccc(C2CCN(CC(F)(F)F)CC2)cc1 | null | null | CO | Reduction | Reduction of primary amides to amines | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccc(C2CCNCC2)cc1 | O=C-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A solution of the formamide in MeOH (20 mL) is stirred at rt and HCl (conc., 1 mL) is added. The deep purple solution is heated at reflux for 1 h, cooled and the MeOH is evaporated. The residue is stirred with water (20 mL) and NaHCO3 (sat. aq.) is added until bubbling ceases. The mixture is extracted with DCM (20 mL, ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1.C1CC[NH]CC1 | Other | CO | null | null | O=CNc1ccc(C2CCN(CC(F)(F)F)CC2)cc1>CO>Nc1ccc(C2CCN(CC(F)(F)F)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c81a802209604c4eadda7d37f101c2c4 | Brc1ncc(Br)n2ncnc12.Nc1ccc(OCCN2CCOCC2)cc1>>Brc1cnc(Nc2ccc(OCCN3CCOCC3)cc2)c2ncnn12 | C(C)(C)N(C(C)C)CC.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.BrC1=CN=C(C=2N1N=CN2)Br.N1(CCOCC1)CCOC1=CC=C(C=C1)N>>BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)OCCN2CCOCC2 | Br[c:5]1[n:4][cH:3][c:2]([Br:1])[n:26]2[c:22]1[n:23][cH:24][n:25]2.[NH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[cH:20][cH:21]1>>[Br:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[cH:20... | Brc1ncc(Br)n2ncnc12.Nc1ccc(OCCN2CCOCC2)cc1 | Brc1cnc(Nc2ccc(OCCN3CCOCC3)cc2)c2ncnn12 | null | null | CC(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | aecfb0ede2c5d7901fea69101287828edf21f7a6e48b6ff83fe43de0688f1ef1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn2ncnc2c(Nc2ccc(OCCN3CCOCC3)cc2)n1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 86.2 | [{"value": 86.0, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)OCCN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.2, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)OCCN2CCOCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 8 | HOUR | According to the procedure described for Compound 6, step 1, 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (0.5 g, 1.799 mmol), 4-(2-morpholin-4-yl-ethoxy)-phenylamine (0.6 g, 4.5 mmol) and N,N-diisopropylethylamine (0.47 mL, 2.7 mmol) in 2-propanol (6 mL) are stirred at 95° C. overnight. After evaporation of the solvent ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cn2ncnc2cn1 | c1cn2ncnc2cn1 | c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | HBr | CC(C)O | 95 | 8 | Brc1ncc(Br)n2ncnc12.Nc1ccc(OCCN2CCOCC2)cc1>CC(C)O>Brc1cnc(Nc2ccc(OCCN3CCOCC3)cc2)c2ncnn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ce1195ef0cd43baac590902bcd96267 | Brc1cnc(Nc2ccc(OCCN3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C>>O=C1NCc2cc(-c3cnc(Nc4ccc(OCCN5CCOCC5)cc4)c4ncnn34)ccc21 | CC1(OB(OC1(C)C)C=1C=C2CNC(C2=CC1)=O)C.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.C(=O)([O-])[O-].[Na+].[Na+].BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)OCCN2CCOCC2>>O1CCN(CC1)CCOC1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C3CNC(C3=CC1)=O)N=CN2 | Br[c:8]1[cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)[cH:26][cH:27]2)[c:28]2[n:29][cH:30][n:31][n:32]12.CC1(C)OB([c:7]2[cH:6][c:5]3[c:35]([cH:34][cH:33]2)[C:2](=[O:1])[NH:3][CH2:4]3)OC1(C)C>>[O:1]=[C:2]1[NH:3][CH2:4][c:5]2[cH:6][c:7](-[c:8]3[... | Brc1cnc(Nc2ccc(OCCN3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C | O=C1NCc2cc(-c3cnc(Nc4ccc(OCCN5CCOCC5)cc4)c4ncnn34)ccc21 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic esters | 0e514a9992c96da29f2ec2414679fb7906a3f635b15b1ade3e33600ae6778418 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | O=C1NCc2cc(-c3cnc(Nc4ccc(OCCN5CCOCC5)cc4)c4ncnn34)ccc21 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-O-C-1(-C)-C>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1):[c:13]:[c:14] | 69 | [{"value": 69.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using the methods as described for Compound 6, step 4, using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-amine (80 mg, 0.19 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one (74 mg, 0.29 mmol), and Pd(PPh3)4 (55 mg, 0.0... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1cn2ncnc2cn1.B1OCCO1.c1ccc2c(c1)CNC2 | c1ccc2c(c1)CNC2.c1cn2ncnc2cn1 | c1ccc2c(c1)CNC2.c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1 | null | null | Brc1cnc(Nc2ccc(OCCN3CCOCC3)cc2)c2ncnn12.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1>O=C1NCc2cc(-c3cnc(Nc4ccc(OCCN5CCOCC5)cc4)c4ncnn34)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac7bb6b97fb5453da4d1ade21276404c | Brc1ncc(Br)n2ncnc12.Nc1ccc(N2CCOCC2)cc1F>>Fc1cc(N2CCOCC2)ccc1Nc1ncc(Br)n2ncnc12 | FC1=C(C=CC(=C1)N1CCOCC1)N.N12CCN(CC1)CC2.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.CCN(C(C)C)C(C)C.BrC1=CN=C(C=2N1N=CN2)Br>>BrC1=CN=C(C=2N1N=CN2)NC2=C(C=C(C=C2)N2CCOCC2)F | Br[c:15]1[n:16][cH:17][c:18]([Br:19])[n:20]2[n:21][cH:22][n:23][c:24]12.[F:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][cH:12][c:13]1[NH2:14]>>[F:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][cH:12][c:13]1[NH:14][c:15]1[n:16][cH:17][c:18]([Br:19])[n:20]2[n:21][cH:22][n:2... | Brc1ncc(Br)n2ncnc12.Nc1ccc(N2CCOCC2)cc1F | Fc1cc(N2CCOCC2)ccc1Nc1ncc(Br)n2ncnc12 | null | null | CC(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | aecfb0ede2c5d7901fea69101287828edf21f7a6e48b6ff83fe43de0688f1ef1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn2ncnc2c(Nc2ccc(N3CCOCC3)cc2)n1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 42 | [{"value": 42.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 1, using 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (0.105 g, 0.89 mmol), 2-fluoro-4-morpholin-4-yl-phenylamine (93 mg, 0.474 mmol), DIPEA (0.123 mL, 0.706 mmol) and 1,4-diazabicyclo[2.2.2]octane (53 mg, 0.472 mmol) in 2-propanol (2 mL). The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cn2ncnc2cn1 | c1cn2ncnc2cn1 | c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | HBr | CC(C)O | null | null | Brc1ncc(Br)n2ncnc12.Nc1ccc(N2CCOCC2)cc1F>CC(C)O>Fc1cc(N2CCOCC2)ccc1Nc1ncc(Br)n2ncnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-49a52185ac7d47708e965d2dad590b46 | CC1(C)OB(c2cn[nH]c2)OC1(C)C.Fc1cc(N2CCOCC2)ccc1Nc1ncc(Br)n2ncnc12>>Fc1cc(N2CCOCC2)ccc1Nc1ncc(-c2cn[nH]c2)n2ncnc12 | C(=O)([O-])[O-].[Na+].[Na+].CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.BrC1=CN=C(C=2N1N=CN2)NC2=C(C=C(C=C2)N2CCOCC2)F.CC1(OB(OC1(C)C)C=1C=NNC1)C>>FC1=C(C=CC(=C1)N1CCOCC1)NC=1C=2N(C(=CN1)C=1C=NNC1)N=CN2 | CC1(C)OB([c:19]2[cH:20][n:21][nH:22][cH:23]2)OC1(C)C.Br[c:18]1[cH:17][n:16][c:15]([NH:14][c:13]2[c:2]([F:1])[cH:3][c:4]([N:5]3[CH2:6][CH2:7][O:8][CH2:9][CH2:10]3)[cH:11][cH:12]2)[c:28]2[n:24]1[n:25][cH:26][n:27]2>>[F:1][c:2]1[cH:3][c:4]([N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[cH:11][cH:12][c:13]1[NH:14][c:15]1[n:16]... | CC1(C)OB(c2cn[nH]c2)OC1(C)C.Fc1cc(N2CCOCC2)ccc1Nc1ncc(Br)n2ncnc12 | Fc1cc(N2CCOCC2)ccc1Nc1ncc(-c2cn[nH]c2)n2ncnc12 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic esters | 3b077e58a8068174133a7eecad35957570f9290725408c31a955826b02d2e470 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3cn[nH]c3)n2n1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[#7;a:13]:[c:14]:2)-O-C-1(-C)-C>>[#7;a:3]1:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[#7;a:13]:[c:14]:2):[c:2]:1 | 38 | [{"value": 38.0, "product": "FC1=C(C=CC(=C1)N1CCOCC1)NC=1C=2N(C(=CN1)C=1C=NNC1)N=CN2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4, using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-(2-fluoro-4-morpholin-4-yl-phenyl)-amine (80 mg, 0.203 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (79 mg, 0.406 mmol), and Pd(PPh3)4 (59 mg, 0.051 mmol) in 1.5N Na... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1cn[nH]c1.c1cn2ncnc2cn1 | c1cn[nH]c1.c1cn2ncnc2cn1 | c1ccccc1.C1COCC[NH]1.c1cn[nH]c1.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1 | null | null | CC1(C)OB(c2cn[nH]c2)OC1(C)C.Fc1cc(N2CCOCC2)ccc1Nc1ncc(Br)n2ncnc12>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1>Fc1cc(N2CCOCC2)ccc1Nc1ncc(-c2cn[nH]c2)n2ncnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0b97dc8358f6448f9d7204d6e5127b9c | CC(C)(C)[Si](C)(C)Cl.OCc1[nH]ncc1Br>>CC(C)(C)[SiH2]OC(C)(C)c1[nH]ncc1Br | C(C)OCC.BrC1=C(NN=C1)CO.[Si](C)(C)(C(C)(C)C)Cl.N1C=NC=C1>>BrC=1C=NNC1C(O[SiH2]C(C)(C)C)(C)C | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:8])[CH3:9].[OH:6][CH2:7][c:10]1[nH:11][n:12][cH:13][c:14]1[Br:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[SiH2:5][O:6][C:7]([CH3:8])([CH3:9])[c:10]1[nH:11][n:12][cH:13][c:14]1[Br:15] | CC(C)(C)[Si](C)(C)Cl.OCc1[nH]ncc1Br | CC(C)(C)[SiH2]OC(C)(C)c1[nH]ncc1Br | null | null | CN(C=O)C | C-C Coupling | OtherReaction | 72a7646acc58c5670b83619272912c04ee14072de109d6c18abcc4d5ec13fed2 | 6b4e12c9a4ccedc8a11bbd8b74fb14ce3d1429a35cd9169d780ad652c7713b04 | c1cn[nH]c1 | Cl-[Si;H0;D4;+0:1](-[CH3;D1;+0:2])(-[CH3;D1;+0:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[OH;D1;+0:8]-[CH2;D2;+0:9]-[c:10]1:[#7;a:11]:[#7;a:12]:[c:13]:[c:14]:1>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[SiH2;D2;+0:1]-[O;H0;D2;+0:8]-[C;H0;D4;+0:9](-[CH3;D1;+0:2])(-[CH3;D1;+0:3])-[c:10]1:[#7;a:11]:[#7;a:12]:... | 98 | [{"value": 98.0, "product": "BrC=1C=NNC1C(O[SiH2]C(C)(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (4-bromo-2H-pyrazol-3-yl)-methanol (0.64 mg, 3.63 mmol), tert-butyldimethylsilyl chloride (0.82 g, 5.45 mmol) and imidazole (0.42 g, 6.18 mmol) in N,N-dimethylformamide (20 mL) is stirred at room temperature overnight. The reaction mixture is diluted with a 50:50 mixture diethyl ether:ethyl acetate and wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | null | null | null | c1cn[nH]c1 | HCl | CN(C=O)C | null | null | CC(C)(C)[Si](C)(C)Cl.OCc1[nH]ncc1Br>CN(C=O)C>CC(C)(C)[SiH2]OC(C)(C)c1[nH]ncc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b51b16d24d9643aebecc23fbf8993b4b | C1=COCCC1.CC(C)(C)[SiH2]OC(C)(C)c1[nH]ncc1Br>>CC(C)(C)[SiH2]OC(C)(C)c1c(Br)cnn1C1CCCCO1.CC(C)(C)[SiH2]OC(C)(C)c1nn(C2CCCCO2)cc1Br | BrC=1C=NNC1C(O[SiH2]C(C)(C)C)(C)C.O1CCCC=C1.[H-].[Na+]>>BrC=1C(=NN(C1)C1OCCCC1)C(O[SiH2]C(C)(C)C)(C)C.BrC=1C=NN(C1C(O[SiH2]C(C)(C)C)(C)C)C1OCCCC1 | [CH2:16]1[CH2:17][CH2:18][CH:19]=[CH:38][O:21]1.[CH3:1][C:2]([SiH2:5][O:6][C:7]([CH3:3])([c:10]1[c:11]([Br:12])[cH:13][n:14][nH:15]1)[CH3:23])([CH3:20])[CH3:36]>>[CH3:1][C:2]([CH3:3])([CH3:4])[SiH2:5][O:6][C:7]([CH3:8])([CH3:9])[c:10]1[c:11]([Br:12])[cH:13][n:14][n:15]1[CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][O:21]1.[C... | C1=COCCC1.CC(C)(C)[SiH2]OC(C)(C)c1[nH]ncc1Br | CC(C)(C)[SiH2]OC(C)(C)c1c(Br)cnn1C1CCCCO1.CC(C)(C)[SiH2]OC(C)(C)c1nn(C2CCCCO2)cc1Br | null | C(=O)(C(F)(F)F)O | null | Aromatic Heterocycle Formation | OtherReaction | 88a97baded83eeb8083ea7731d7e5aac9e2c1855aabd5adda9923edfb9093a2e | b856992715d7b099e07bf70aa7d3c0c9c5967b1df181936fb26bd813f188f1b0 | c1cnn(C2CCCCO2)c1.c1cnn(C2CCCCO2)c1 | [C;D1;H3:1]-[C;H0;D4;+0:2](-[CH3;D1;+0:3])(-[CH3;D1;+0:4])-[#14:5]-[#8:6]-[C;H0;D4;+0:7](-[CH3;D1;+0:8])(-[CH3;D1;+0:9])-[c:10]1:[c:11]:[c:12]:[#7;a:13]:[nH;D2;+0:14]:1.[C:15]1-[C:16]-[CH;D2;+0:17]=[CH;D2;+0:18]-[O;H0;D2;+0:19]-[CH2;D2;+0:20]-1>>[#8:21]-[#14:22]-[C;H0;D4;+0:8](-[C;D1;H3:23])(-[C;D1;H3:24])-[C;D1;H3:25]... | 111.8 | [{"value": 56.0, "product": "BrC=1C=NN(C1C(O[SiH2]C(C)(C)C)(C)C)C1OCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 111.8, "product": "BrC=1C=NN(C1C(O[SiH2]C(C)(C)C)(C)C)C1OCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 18 | HOUR | 4-Bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-1H-pyrazole (1 g, 3.45 mmol) is dissolved in 3,4-dihydro-2H-pyran (0.944 mL, 10.34 mmol) in the presence of a catalytic amount of TFA (0.0026 mL, 0.035 mmol). The reaction mixture is stirred at 90° C. for 18 hours, cooled and then quenched using NaH (4.69 mg, 0.206 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic halide.Ether.Ether | C1=COCCC1.c1cn[nH]c1 | c1cn[nH]c1.C1CCOCC1.c1c[nH]nc1.C1CCOCC1 | c1cn[nH]c1.C1CCOCC1.c1c[nH]nc1.C1CCOCC1 | Other | C(=O)(C(F)(F)F)O | 90 | 18 | C1=COCCC1.CC(C)(C)[SiH2]OC(C)(C)c1[nH]ncc1Br>C(=O)(C(F)(F)F)O>CC(C)(C)[SiH2]OC(C)(C)c1c(Br)cnn1C1CCCCO1.CC(C)(C)[SiH2]OC(C)(C)c1nn(C2CCCCO2)cc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2603bbe820c04d83bd8522fba1cbcf86 | CC(C)(C)[SiH2]OC(C)(C)c1c(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c3ncnn23)cnn1C1CCCOC1>>OCc1[nH]ncc1-c1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12 | C(C)(C)(C)[SiH2]OC(C1=NN(C=C1C1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2)C2COCCC2)(C)C.C(C)(C)(C)[SiH2]OC(C1=C(C=NN1C1COCCC1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCOCC2)(C)C.Cl>>O1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=NNC1CO)N=CN2 | CC(C)(C)[SiH2][O:1][C:2](C)(C)[c:3]1[n:4](C2CCCOC2)[n:5][cH:6][c:7]1-[c:8]1[cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][c:16]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[cH:23][cH:24]2)[c:25]2[n:26][cH:27][n:28][n:29]12>>[OH:1][CH2:2][c:3]1[nH:4][n:5][cH:6][c:7]1-[c:8]1[cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH... | CC(C)(C)[SiH2]OC(C)(C)c1c(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c3ncnn23)cnn1C1CCCOC1 | OCc1[nH]ncc1-c1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12 | null | null | CO | Reduction | OtherReaction | b83aaa72880f67296b021396a923e807e99ab3f7555f05c773f6f062a070e931 | f3c13c34886a9ee39fc7fda8af9901946f6871b5562065675a15384eea5a8281 | c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3cn[nH]c3)n2n1 | C-C(-C)(-C)-[SiH2]-[O;H0;D2;+0:1]-[C;H0;D4;+0:2](-C)(-C)-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[n;H0;D3;+0:7]:1-C1-C-C-C-O-C-1>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[nH;D2;+0:7]:1 | null | [] | null | null | null | null | A solution of {5-[3-(tert-butyl-dimethyl-silanyloxymethyl)-1-(tetrahydro-pyran-3-yl)-1H-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyrazin-8-yl}-(4-morpholin-4-yl-phenyl)-amine and {5-[5-(tert-butyl-dimethyl-silanyloxymethyl)-1-(tetrahydro-pyran-3-yl)-1H-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyrazin-8-yl}-(4-morpholin-4-yl-phen... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol | c1c[nH]nc1.C1CCOCC1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.C1COCC[NH]1.c1cn2ncnc2cn1 | HO- | CO | null | null | CC(C)(C)[SiH2]OC(C)(C)c1c(-c2cnc(Nc3ccc(N4CCOCC4)cc3)c3ncnn23)cnn1C1CCCOC1>CO>OCc1[nH]ncc1-c1cnc(Nc2ccc(N3CCOCC3)cc2)c2ncnn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5cf2e3e58a684a6fa54fbb1657752f1f | Brc1csc(Br)n1.CCOC(=O)OCC>>CCOC(=O)c1nc(Br)cs1 | C(OCC)(OCC)=O.BrC=1N=C(SC1)Br.C(C)(C)[Mg]Cl>>C(C)OC(=O)C=1SC=C(N1)Br | Br[c:6]1[n:7][c:8]([Br:9])[cH:10][s:11]1.CCO[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([Br:9])[cH:10][s:11]1 | Brc1csc(Br)n1.CCOC(=O)OCC | CCOC(=O)c1nc(Br)cs1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | eab4ec716edd47997f05b163a3ca9951e72a9d65e1083e2714b5da93c90a3eb8 | bcd3559e95d57605d0e6e7a6ba9cc016318f006dee2eacb538f0c39f9d5391eb | c1cscn1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.C-C-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[#8:8]-[C:9]>>[C:9]-[#8:8]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1 | 52 | [{"value": 52.0, "product": "C(C)OC(=O)C=1SC=C(N1)Br", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 0.25 | HOUR | To a solution of dibromothiazole (1 g, 4.15 mmol) in THF (15 mL) at 0° C., is added dropwise a solution of iPrMgCl in THF (2 M, 2.3 mL, 4.57 mmol, 1.10 equiv.). The reaction is stirred at 0° C. for 0.25 h. To the resulting orange solution is added via a cannula, diethyl carbonate (3 mL) in THF (5 ml). The resulting gre... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbonic Ester | Ester | c1cscn1 | c1cscn1 | c1cscn1 | HBr | C1CCOC1 | 0 | 0.25 | Brc1csc(Br)n1.CCOC(=O)OCC>C1CCOC1>CCOC(=O)c1nc(Br)cs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d3bbd687e934429f83c1107e159f79da | CCOC(=O)c1nc(Br)cs1.CN>>CNC(=O)c1nc(Br)cs1 | C(C)OC(=O)C=1SC=C(N1)Br.CN>>CNC(=O)C=1SC=C(N1)Br | CCO[C:3](=[O:4])[c:5]1[n:6][c:7]([Br:8])[cH:9][s:10]1.[CH3:1][NH2:2]>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[n:6][c:7]([Br:8])[cH:9][s:10]1 | CCOC(=O)c1nc(Br)cs1.CN | CNC(=O)c1nc(Br)cs1 | null | null | CO | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1cscn1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[c:6]:[#7;a:7]:1.[C;D1;H3:8]-[NH2;D1;+0:9]>>[C;D1;H3:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[c:6]:[#7;a:7]:1 | null | [] | null | null | 8 | HOUR | 4-Bromothiazole-2-carboxylic acid ethyl ester (500 mg, 2.13 mmol) is dissolved in methanol (1 mL) and methyl amine in methanol (10 mL) is added. The mixture is stirred overnight at room temperature. Evaporation of the solvent under reduced pressure affords the title compound as yellow solid. LCMS: Rt 0.92 min (100%) m/... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1cscn1 | HO- | CO | null | 8 | CCOC(=O)c1nc(Br)cs1.CN>CO>CNC(=O)c1nc(Br)cs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6069cd44fe0e4069aeb6700cbe77f949 | COC(=O)c1ccc(Br)cc1CBr.N>>O=C1NCc2cc(Br)ccc21 | COC(C1=C(C=C(C=C1)Br)CBr)=O.N>>BrC=1C=C2CNC(C2=CC1)=O | CO[C:2](=[O:1])[c:11]1[c:5]([CH2:4]Br)[cH:6][c:7]([Br:8])[cH:9][cH:10]1.[NH3:3]>>[O:1]=[C:2]1[NH:3][CH2:4][c:5]2[cH:6][c:7]([Br:8])[cH:9][cH:10][c:11]21 | COC(=O)c1ccc(Br)cc1CBr.N | O=C1NCc2cc(Br)ccc21 | null | null | null | Acylation | OtherReaction | bfe20f0aa9f011cd97f8730d82b7c7716781d101d55a13d6080c38f132dfa20e | 64fe73e2e83384d508c35f2187876b5b9badfa6118b2f44eff0dc89bfcf766e3 | O=C1NCc2ccccc21 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-O-C):[c:7].[NH3;D0;+0:8]>>[O;D1;H0:6]=[C;H0;D3;+0:5]1-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-1:[c:7] | 65 | [{"value": 65.0, "product": "BrC=1C=C2CNC(C2=CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Bromo-2-bromomethyl-benzoic acid methyl ester (0.5 g, 16.2 mmol) is treated with methanolic ammonia (10 mL, 7 N NH3 in MeOH) for 5 minutes at 90° C. After cooling to room temperature a precipitate is formed, collected by filtration and washed with a small amount of methanol to afford the title compound as a colourles... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Secondary amide | null | c1ccc2c(c1)CNC2 | c1ccc2c(c1)CNC2 | HBr | null | null | null | COC(=O)c1ccc(Br)cc1CBr.N>>O=C1NCc2cc(Br)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b08441a8fae42b5aa4c28a3eb8bc8dc | CC(C)N1CCNCC1.O=[N+]([O-])c1ccc(Cl)nc1>>CC(C)N1CCN(c2ccc([N+](=O)[O-])cn2)CC1 | ClC1=NC=C(C=C1)[N+](=O)[O-].C(C)(C)N1CCNCC1.C(=O)([O-])[O-].[K+].[K+]>>C(C)(C)N1CCN(CC1)C1=NC=C(C=C1)[N+](=O)[O-] | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][NH:7][CH2:17][CH2:18]1.Cl[c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][n:16]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][n:16]2)[CH2:17][CH2:18]1 | CC(C)N1CCNCC1.O=[N+]([O-])c1ccc(Cl)nc1 | CC(C)N1CCN(c2ccc([N+](=O)[O-])cn2)CC1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | fa523b05de53c4b0abc4cfee73617ebc93929b0985f4e85a4f5201b7c9df83f1 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[#7;a:2]:[c:3] | null | [] | 50 | CELSIUS | 4 | HOUR | To a solution of 2-chloro-5-nitropyridine (2.5 g, 15.7 mmol) in THF (25 mL), are added 1-isopropylpiperazine (2.01 g, 15.7 mmol) and K2CO3 (3.25 g, 23.6 mmol). The reaction mixture is stirred at 50° C. for 4 hours and then at 70° C. overnight. The solvent is removed in vacuo and the resultant orange solid is triturated... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1 | C1C[NH]CC[NH]1.c1ccncc1 | HCl | C1CCOC1 | 50 | 4 | CC(C)N1CCNCC1.O=[N+]([O-])c1ccc(Cl)nc1>C1CCOC1>CC(C)N1CCN(c2ccc([N+](=O)[O-])cn2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c30382f053ff4f0eb8c94e28cb95ba2f | CC(C)N1CCN(c2ccc([N+](=O)[O-])cn2)CC1>>CC(C)N1CCN(c2ccc(N)cn2)CC1 | C(C)(C)N1CCN(CC1)C1=NC=C(C=C1)[N+](=O)[O-].O.O.[Sn](Cl)Cl.Cl>>C(C)(C)N1CCN(CC1)C1=CC=C(C=N1)N | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]([N:7]2[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:16][CH2:15]2)[n:14][cH:13]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:13][n:14]2)[CH2:15][CH2:16]1 | CC(C)N1CCN(c2ccc([N+](=O)[O-])cn2)CC1 | CC(C)N1CCN(c2ccc(N)cn2)CC1 | null | null | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCNCC2)nc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 86 | [{"value": 86.0, "product": "C(C)(C)N1CCN(CC1)C1=CC=C(C=N1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.7, "product": "C(C)(C)N1CCN(CC1)C1=CC=C(C=N1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 1-Isopropyl-4-(5-nitro-pyridin-2-yl)-piperazine (0.9 g, 3.6 mmol) is dissolved in MeOH (20 mL) and tin (II) dichloride dihydrate (4 g, 18 mmol) is added. The mixture is cooled using a water bath and conc. HCl is added (4 mL). The reaction is stirred at room temperature overnight. After removing the methanol, the result... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]CC[NH]1.c1ccncc1 | Other | CO | null | 8 | CC(C)N1CCN(c2ccc([N+](=O)[O-])cn2)CC1>CO>CC(C)N1CCN(c2ccc(N)cn2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bd472570412c4388a8695015086d4763 | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cn2)CC1.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C>>CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccc5c(c4)CNC5=O)n4ncnc34)cn2)CC1 | CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.BrC1=CN=C(C=2N1N=CN2)NC=2C=NC(=CC2)N2CCN(CC2)C(C)C.CC1(OB(OC1(C)C)C=1C=C2CNC(C2=CC1)=O)C>>C(C)(C)N1CCN(CC1)C1=CC=C(C=N1)NC=1C=2N(C(=CN1)C=1C=C3CNC(C3=CC1)=O)N=CN2 | Br[c:16]1[cH:15][n:14][c:13]([NH:12][c:11]2[cH:10][cH:9][c:8]([N:7]3[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:35][CH2:34]3)[n:33][cH:32]2)[c:31]2[n:27]1[n:28][cH:29][n:30]2.CC1(C)OB([c:17]2[cH:18][cH:19][c:20]3[c:21]([cH:22]2)[CH2:23][NH:24][C:25]3=[O:26])OC1(C)C>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][N:7]([... | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cn2)CC1.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C | CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccc5c(c4)CNC5=O)n4ncnc34)cn2)CC1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+] | C-C Coupling | Suzuki coupling with boronic esters | 0e514a9992c96da29f2ec2414679fb7906a3f635b15b1ade3e33600ae6778418 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | O=C1NCc2cc(-c3cnc(Nc4ccc(N5CCNCC5)nc4)c4ncnn34)ccc21 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-O-C-1(-C)-C>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1):[c:13]:[c:14] | null | [] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4, using 5-bromo-N-(6-(4-isopropylpiperazin-1-yl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine (50 mg, 0.12 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one (56 mg, 0.216 mmol) and Pd(PPh3)4 (35 mg, 0.0... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1cn2ncnc2cn1.B1OCCO1.c1ccc2c(c1)CNC2 | c1ccc2c(c1)CNC2.c1cn2ncnc2cn1 | C1C[NH]CC[NH]1.c1ccncc1.c1ccc2c(c1)CNC2.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+] | null | null | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cn2)CC1.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccc5c(... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-724cebcaefc44d49bb6b890480f69a3c | CCOC(CBr)OCC.Sc1ccccc1Br>>CCOC=CSc1ccccc1Br | O.BrCC(OCC)OCC.BrC1=C(C=CC=C1)S.C([O-])([O-])=O.[K+].[K+]>>BrC1=C(C=CC=C1)SC=COCC | CCO[CH:4]([O:3][CH2:2][CH3:1])[CH2:5]Br.[SH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[Br:13]>>[CH3:1][CH2:2][O:3][CH:4]=[CH:5][S:6][c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[Br:13] | CCOC(CBr)OCC.Sc1ccccc1Br | CCOC=CSc1ccccc1Br | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | a25c6e5ccd76fa864f6dd7ef671ee1eef69d64bf541b51af8438489add3390ca | bc651cc20acc61bf6e1ff09b340bd291b6db4e7662a32e932f07f0a8e438a76d | c1ccccc1 | Br-[CH2;D2;+0:1]-[CH;D3;+0:2](-O-C-C)-[#8:3]-[C:4].[SH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[#8:3]-[CH;D2;+0:2]=[CH;D2;+0:1]-[S;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 2 | HOUR | To a solution of 2-bromothiophenol (10.50 g, 55.87 mmol) in dry DMF (50 mL) under nitrogen is added cautiously potassium carbonate (9.2 mL, 61.46 mmol, 1.10 equiv.). Once bubbling has subsided, 2-bromo-1,1-diethoxyethane (8.46 g, 61.46 mmol, 1.10 equiv.) is added to the mixture and stirred for 2 h at room temperature. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether.Aromatic thiol | Ether.Monosulfide | null | null | c1ccccc1 | HBr | CN(C)C=O | null | 2 | CCOC(CBr)OCC.Sc1ccccc1Br>CN(C)C=O>CCOC=CSc1ccccc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-25bb78cf37ed41c68f9f83ba102f470d | CCOC=CSc1ccccc1Br>>Brc1cccc2ccsc12 | BrC1=C(C=CC=C1)SC=COCC>>BrC1=CC=CC2=C1SC=C2 | CCO[CH:7]=[CH:8][S:9][c:10]1[c:2]([Br:1])[cH:3][cH:4][cH:5][cH:6]1>>[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[cH:7][cH:8][s:9][c:10]12 | CCOC=CSc1ccccc1Br | Brc1cccc2ccsc12 | null | null | ClC1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 3b3a47e1a37723cb89ea18d12710cf7a4e1e15dc1cbc211627933afbf6616922 | 4b36a288ef2269f6b903f0d10e5fd047b6de50e118af8eebc52b54cdfe6597f4 | c1ccc2sccc2c1 | C-C-O-[CH;D2;+0:1]=[CH;D2;+0:2]-[S;H0;D2;+0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[c:5]:[c:4]1:[s;H0;D2;+0:3]:[cH;D2;+0:2]:[cH;D2;+0:1]:[c;H0;D3;+0:6]:1:[c:7]:[c:8] | 35 | [{"value": 35.0, "product": "BrC1=CC=CC2=C1SC=C2", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | 1-Bromo-2-(2-ethoxyvinylsulfanyl)benzene is dissolved in chlorobenzene (50 mL) and the solution is heated to 70° C. PPA (10.5 mL) is then added carefully and the biphasic mixture is heated at 150° C. overnight. The resulting dark syrup is allowed to cool down and the supernatant solvent removed by pipette. Chlorobenzen... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Monosulfide | null | c1ccccc1 | c1ccc2sccc2c1 | c1ccc2sccc2c1 | HO- | ClC1=CC=CC=C1 | 70 | null | CCOC=CSc1ccccc1Br>ClC1=CC=CC=C1>Brc1cccc2ccsc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8557a574f6614ac88eef6422d26425a2 | Brc1cccc2ccsc12.CCOC(=O)OCC>>CCOC(=O)c1cccc2ccsc12 | C(OCC)(OCC)=O.BrC1=CC=CC2=C1SC=C2.[Mg].[Cl-].[NH4+].[Mg]>>C(C)OC(=O)C1=CC=CC2=C1SC=C2 | Br[c:6]1[cH:7][cH:8][cH:9][c:10]2[cH:11][cH:12][s:13][c:14]12.CCO[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]2[cH:11][cH:12][s:13][c:14]12 | Brc1cccc2ccsc12.CCOC(=O)OCC | CCOC(=O)c1cccc2ccsc12 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 1f5ef588d5d8a9fcdbeceb32da0c7a3570945b63c30fa4b3e818afd47f4f8213 | bcd3559e95d57605d0e6e7a6ba9cc016318f006dee2eacb538f0c39f9d5391eb | c1ccc2sccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#16;a:6]:[c:7].C-C-O-[C;H0;D3;+0:8](=[O;D1;H0:9])-[#8:10]-[C:11]>>[C:11]-[#8:10]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#16;a:6]:[c:7] | 71 | [{"value": 71.0, "product": "C(C)OC(=O)C1=CC=CC2=C1SC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 7-bromobenzo[b]thiophene (500 mg, 2.36 mmol) is dissolved in dry THF (5.0 mL) under nitrogen. Magnesium turnings (530 mg, 2.83 mmol, 1.20 equiv.) are added and the resulting mixture is heated at reflux until dissolution of the magnesium has occurred. The resulting cloudy yellow solution is allowed to cool to rt and die... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbonic Ester | Ester | c1ccc2sccc2c1 | c1ccc2sccc2c1 | c1ccc2sccc2c1 | HBr | C1CCOC1 | null | 1 | Brc1cccc2ccsc12.CCOC(=O)OCC>C1CCOC1>CCOC(=O)c1cccc2ccsc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1dccd73d7787490ab03944c011c536cb | CCOC(=O)c1cccc2ccsc12>>O=C(O)c1cccc2ccsc12 | C(C)OC(=O)C1=CC=CC2=C1SC=C2.[OH-].[Na+]>>S1C2=C(C=C1)C=CC=C2C(=O)O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:10][s:11][c:12]12>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:10][s:11][c:12]12 | CCOC(=O)c1cccc2ccsc12 | O=C(O)c1cccc2ccsc12 | null | null | O.CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2sccc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#16;a:6]>>[#16;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 59 | [{"value": 59.0, "product": "S1C2=C(C=C1)C=CC=C2C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 5.9, "product": "S1C2=C(C=C1)C=CC=C2C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of benzo[b]thiophene-7-carboxylic acid ethyl ester (1.0 g, 48 mmol) in methanol (10 mL) and water (10 mL) is added sodium hydroxide (5 g, excess). The solution is stirred at room temperature for 30 min; at which point all the ester has been consumed. The reaction mixture is adjusted to pH 1 by adding 6M H... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2sccc2c1 | Other | O.CO | null | 0.5 | CCOC(=O)c1cccc2ccsc12>O.CO>O=C(O)c1cccc2ccsc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1e72ea23b8e744db9713ae2ea73eeea8 | N.O=C(O)c1cccc2ccsc12>>NC(=O)c1cccc2ccsc12 | C(=O)(O)[O-].[Na+].S(=O)(Cl)Cl.S1C2=C(C=C1)C=CC=C2C(=O)O.N>>S1C2=C(C=C1)C=CC=C2C(=O)N | [NH3:1].O[C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:10][s:11][c:12]12>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:10][s:11][c:12]12 | N.O=C(O)c1cccc2ccsc12 | NC(=O)c1cccc2ccsc12 | null | null | ClCCl.O.CN(C)C=O | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | c1ccc2sccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](:[c:6]):[#16;a:7]:[c:8].[NH3;D0;+0:9]>>[NH2;D1;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](:[c:6]):[#16;a:7]:[c:8] | null | [] | null | null | 1 | HOUR | A solution of benzo[b]thiophene-7-carboxylic acid (505 mg, 2.84 mmol) in dichloromethane (10 mL) is stirred at rt and thionyl chloride (669 mg, 5.68 mmol, 2.0 equiv.) is added, followed by DMF (0.06 mL), causing gas evolution. The resulting solution is stirred at rt for 1 hour. Aqueous ammonia (10 mL) is then added cau... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccc2sccc2c1 | HO- | ClCCl.O.CN(C)C=O | null | 1 | N.O=C(O)c1cccc2ccsc12>ClCCl.O.CN(C)C=O>NC(=O)c1cccc2ccsc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a836a09183040de83db5060b8063243 | NC(=O)c1cccc2ccsc12.O=C1CCC(=O)N1Br>>NC(=O)c1cccc2c(Br)csc12 | C(C)(=O)O.S1C2=C(C=C1)C=CC=C2C(=O)N.C1CC(=O)N(C1=O)Br>>BrC=1C2=C(SC1)C(=CC=C2)C(=O)N | [NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[cH:9][cH:11][s:12][c:13]12.O=C1CCC(=O)N1[Br:10]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]([Br:10])[cH:11][s:12][c:13]12 | NC(=O)c1cccc2ccsc12.O=C1CCC(=O)N1Br | NC(=O)c1cccc2c(Br)csc12 | null | null | ClCCl | Functional Group Interconversion | Bromination | e44d0870c7c18b28c8897b5e91cec6d880d9714f95f6ff4571946e55f765cc6c | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc2sccc2c1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[N;D1;H2:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]1:[#16;a:7]:[c:8]:[cH;D2;+0:9]:[c:10]:1:[c:11]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:9]1:[c:8]:[#16;a:7]:[c:6](:[c:5]-[C:3](-[N;D1;H2:2])=[O;D1;H0:4]):[c:10]:1:[c:11] | 79 | [{"value": 79.0, "product": "BrC=1C2=C(SC1)C(=CC=C2)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of benzo[b]thiophene-7-carboxylic acid amide (500 mg, 2.82 mmol) in dichloromethane (5 mL) is stirred at rt and acetic acid (5 mL) is added followed by NBS (750 mg, 4.23 mmol, 1.5 equiv.). The reaction is stirred at room temperature for 1 hour at which point LC-MS analysis shows full conversion of the starti... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2sccc2c1.C1CCNC1 | c1ccc2sccc2c1 | c1ccc2sccc2c1 | HO- | ClCCl | null | 1 | NC(=O)c1cccc2ccsc12.O=C1CCC(=O)N1Br>ClCCl>NC(=O)c1cccc2c(Br)csc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-28eca8fe9b3f4156b195ed7665d89339 | Cc1cc(Br)ccn1>>Cc1cc(Br)cc[n+]1[O-] | BrC1=CC(=NC=C1)C.C1=CC(=CC(=C1)Cl)C(=O)OO>>BrC1=CC(=[N+](C=C1)[O-])C | [CH3:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][cH:7][n:8]1>>[CH3:1][c:2]1[cH:3][c:4]([Br:5])[cH:6][cH:7][n+:8]1[O-:9] | Cc1cc(Br)ccn1 | Cc1cc(Br)cc[n+]1[O-] | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 54415aed4bb61f76efee9ed140374352608210a9fed7c372975c12eb7023cea2 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1cc[nH+]cc1 | [C;D1;H3:1]-[c:2](:[c:3]):[n;H0;D2;+0:4]:[c:5]:[c:6]>>[C;D1;H3:1]-[c:2](:[c:3]):[n+;H0;D3:4](-[O;-;D1;H0:7]):[c:5]:[c:6] | null | [] | null | null | 3 | HOUR | A solution of 4-bromo-2-methylpyridine (5 g, 29 mmol) in DCM (20 mL) is cooled to 0° C. and m-CPBA (7.55 g, 43.87 mmol, 1.5 equiv.) is added portionwise over 30 min. The ice bath is then removed and the mixture is allowed to stir at room temperature for 3 hours. The resulting solution is diluted with sodium bicarbonate... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | null | C(Cl)Cl | null | 3 | Cc1cc(Br)ccn1>C(Cl)Cl>Cc1cc(Br)cc[n+]1[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0c44e6b863894bd3bbec0160a1725659 | CC(=O)OC(C)=O.Cc1cc(Br)cc[n+]1[O-]>>CC(=O)OCc1cc(Br)ccn1 | BrC1=CC(=[N+](C=C1)[O-])C.C(C)(=O)OC(C)=O>>BrC1=CC(=NC=C1)COC(C)=O | CC(=O)[O:4][C:2]([CH3:1])=[O:3].[O-][n+:12]1[c:6]([CH3:5])[cH:7][c:8]([Br:9])[cH:10][cH:11]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][cH:11][n:12]1 | CC(=O)OC(C)=O.Cc1cc(Br)cc[n+]1[O-] | CC(=O)OCc1cc(Br)ccn1 | null | null | C(Cl)Cl | Protection | OtherReaction | f4e85b633bf4e79d1b81c036d2f4e246a93c2eb8ec0202f93c45d73e710e4f0d | dd0b9e5a615173b1d6c9fe991a352f69d24fef80f4bf0eeab7c46667d446dcd0 | c1ccncc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].[CH3;D1;+0:5]-[c:6](:[c:7]):[n+;H0;D3:8](-[O-]):[c:9]:[c:10]>>[C;D1;H3:3]-[C:2](=[O;D1;H0:4])-[O;H0;D2;+0:1]-[CH2;D2;+0:5]-[c:6](:[c:7]):[n;H0;D2;+0:8]:[c:9]:[c:10] | null | [] | null | null | 1 | HOUR | To a solution of 4-bromo-2-methylpyridine-1-oxide (4.00 g, 21.40 mmol) in DCM (20 mL) is added acetic anhydride (6 mL). The mixture is stirred at room temperature for 1 hour and then heated at reflux overnight. The solvent is removed under vacuum and the crude product is filtered through a silica plug, eluting with DCM... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Ester | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1 | HO- | C(Cl)Cl | null | 1 | CC(=O)OC(C)=O.Cc1cc(Br)cc[n+]1[O-]>C(Cl)Cl>CC(=O)OCc1cc(Br)ccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe5a3b077fb944c992dad3b05162cbbe | CC(=O)OCc1cc(B2OC(C)(C)C(C)(C)O2)ccn1.CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1>>CC(=O)OCc1cc(-c2cnc(Nc3ccc(N4CCN(C(C)C)CC4)cc3)c3ncnn23)ccn1 | BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCN(CC2)C(C)C.C([O-])([O-])=O.[K+].[K+].CC1(OB(OC1(C)C)C1=CC(=NC=C1)COC(C)=O)C>>C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C1=CC(=NC=C1)COC(C)=O)N=CN2 | CC1(C)OB([c:8]2[cH:7][c:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])[n:36][cH:35][cH:34]2)OC1(C)C.Br[c:9]1[cH:10][n:11][c:12]([NH:13][c:14]2[cH:15][cH:16][c:17]([N:18]3[CH2:19][CH2:20][N:21]([CH:22]([CH3:23])[CH3:24])[CH2:25][CH2:26]3)[cH:27][cH:28]2)[c:29]2[n:30][cH:31][n:32][n:33]12>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[cH... | CC(=O)OCc1cc(B2OC(C)(C)C(C)(C)O2)ccn1.CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1 | CC(=O)OCc1cc(-c2cnc(Nc3ccc(N4CCN(C(C)C)CC4)cc3)c3ncnn23)ccn1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | O1CCOCC1.O | C-C Coupling | Suzuki coupling with boronic esters | 08de20b28f3001ce42d0191b8d9e5679e0920ef2236528a84beaa5bda4d8d3e0 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1cc(-c2cnc(Nc3ccc(N4CCNCC4)cc3)c3ncnn23)ccn1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10]2:[c:11]:[c:12]:[#7;a:13]:[c:14](-[C:15]):[c:16]:2)-O-C-1(-C)-C>>[C:15]-[c:14]1:[#7;a:13]:[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[#7;a:3]:[c:4]:[c:5]3:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:3:2):[c:1... | null | [] | null | null | null | null | A suspension of (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(4-isopropyl-piperazin-1-yl)phenyl]amine (300 mg, 0.723 mmol) and Pd(dppf)Cl2 (59 mg, 10 mol %) in 4/1 dioxane/water (5 mL) is stirred at rt and potassium carbonate (200 mg, 1.45 mmol, 2.0 equiv.) and acetic acid 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccncc1.c1cn2ncnc2cn1 | c1ccncc1.c1cn2ncnc2cn1 | c1ccncc1.c1ccccc1.C1C[NH]CC[NH]1.c1cn2ncnc2cn1 | HBr.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O | null | null | CC(=O)OCc1cc(B2OC(C)(C)C(C)(C)O2)ccn1.CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O>CC(=O)OCc1cc(-c2cnc(Nc3ccc(N4CCN(C(C)C)CC4)cc3)c3ncnn23)ccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-45edd5e34d214dc19202bd9f88e1479c | CC(=O)OCc1cc(-c2cnc(Nc3ccc(N4CCN(C(C)C)CC4)cc3)c3ncnn23)ccn1>>CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccnc(CO)c4)n4ncnc34)cc2)CC1 | C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C1=CC(=NC=C1)COC(C)=O)N=CN2.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C1=CC(=NC=C1)CO)N=CN2 | CC(=O)[O:23][CH2:22][c:21]1[n:20][cH:19][cH:18][c:17](-[c:16]2[cH:15][n:14][c:13]([NH:12][c:11]3[cH:10][cH:9][c:8]([N:7]4[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:33][CH2:32]4)[cH:31][cH:30]3)[c:29]3[n:25]2[n:26][cH:27][n:28]3)[cH:24]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH... | CC(=O)OCc1cc(-c2cnc(Nc3ccc(N4CCN(C(C)C)CC4)cc3)c3ncnn23)ccn1 | CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccnc(CO)c4)n4ncnc34)cc2)CC1 | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1cc(-c2cnc(Nc3ccc(N4CCNCC4)cc3)c3ncnn23)ccn1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[c:3]:[#7;a:4]>>[#7;a:4]:[c:3]-[C:2]-[OH;D1;+0:1] | 12.5 | [{"value": 12.5, "product": "C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C1=CC(=NC=C1)CO)N=CN2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Acetic acid 4-{8-[4-(4-isopropylpiperazin-1-yl)phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}pyridin-2-ylmethyl ester is stirred at room temperature overnight in 10 mL of a 1.5 M solution of potassium carbonate in methanol. The pH is then brought to neutral by addition of 10% aqueous citric acid and the mixture is ex... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccncc1.c1cn2ncnc2cn1 | HO- | CO | null | null | CC(=O)OCc1cc(-c2cnc(Nc3ccc(N4CCN(C(C)C)CC4)cc3)c3ncnn23)ccn1>CO>CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccnc(CO)c4)n4ncnc34)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e652935c29cc4a9a9e672a5a24d1ecaa | CC(C)N1CCNCC1.O=[N+]([O-])c1ccc(F)cc1>>CC(C)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1.N | FC1=CC=C(C=C1)[N+](=O)[O-].C(C)(C)N1CCNCC1.C(=O)([O-])[O-].[K+].[K+]>>N.C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-] | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][NH:7][CH2:17][CH2:18]1.F[c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[CH2:17][CH2:18]1.[NH3:19] | CC(C)N1CCNCC1.O=[N+]([O-])c1ccc(F)cc1 | CC(C)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1.N | null | null | C1CCOC1 | Functional Group Interconversion | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | c6c38d29142a1aca5d86f02d4b0c2562460ca1aec33aa213f11cd4062c6e7363 | 39ece5c8e1ec3e350cfadd8e37bb010493b934313e1cd5367f16de670d62b5af | c1ccc(N2CCNCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:2]:[c:3] | 185.8 | [{"value": 94.0, "product": "C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 185.8, "product": "C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 4-fluoronitrobenzene (5 g, 35.4 mmol) in THF (50 mL), 1-isopropylpiperazine (4.54 g, 35.4 mmol) and K2CO3 (7.35 g, 53.2 mmol) are added. The reaction mixture is stirred at room temperature overnight. The solvent is removed in vacuo and the residue is partitioned between EtOAc and water. The organic lay... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | null | C1CCOC1 | null | 8 | CC(C)N1CCNCC1.O=[N+]([O-])c1ccc(F)cc1>C1CCOC1>CC(C)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1.N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0b4e96c71ba444429a7116839d07adb3 | CC(C)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1>>CC(C)N1CCN(c2ccc(N)cc2)CC1 | C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-].O.O.[Sn](Cl)Cl.Cl>>C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)N | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]([N:7]2[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:16][CH2:15]2)[cH:14][cH:13]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:13][cH:14]2)[CH2:15][CH2:16]1 | CC(C)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1 | CC(C)N1CCN(c2ccc(N)cc2)CC1 | null | null | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCNCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 88 | [{"value": 88.0, "product": "C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.9, "product": "C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 1-Isopropyl-4-(4-nitro-phenyl)-piperazine (8.3 g, 33.2 mmol) is dissolved in MeOH (120 mL) and tin (II) dichloride dihydrate (37.4 g, 0.165 mol) is added. The mixture is cooled using a water bath and conc. HCl is added (36 mL). The reaction is stirred at room temperature overnight. After removing the methanol, the resu... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | CO | null | 8 | CC(C)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1>CO>CC(C)N1CCN(c2ccc(N)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2451d9c658d64830b9e953833027103d | Brc1ncc(Br)n2ncnc12.CC(C)N1CCN(c2ccc(N)cc2)CC1>>CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1 | C(C)(C)N(C(C)C)CC.BrC1=CN=C(C=2N1N=CN2)Br.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)N>>BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCN(CC2)C(C)C | Br[c:13]1[n:14][cH:15][c:16]([Br:17])[n:18]2[n:19][cH:20][n:21][c:22]12.[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:23][cH:24]2)[CH2:25][CH2:26]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH:12][c:13]3[n:14][cH:15][c:16]([Br:17])[n:18]4[n:19][... | Brc1ncc(Br)n2ncnc12.CC(C)N1CCN(c2ccc(N)cc2)CC1 | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1 | null | null | CC(C)O.C(C)OCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | aecfb0ede2c5d7901fea69101287828edf21f7a6e48b6ff83fe43de0688f1ef1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn2ncnc2c(Nc2ccc(N3CCNCC3)cc2)n1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | null | [] | 95 | CELSIUS | 8 | HOUR | This compound may be prepared using methods as described for Compound 6, step 1, using 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (2 g, 7.20 mmol), 4-(4-isopropyl-piperazin-1-yl)-phenylamine (1.89 g, 8.62 mmol) and N,N-diisopropylethylamine (1.88 mL, 10.8 mmol) in 2-propanol (30 mL) are stirred at 95° C. overnight. The... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cn2ncnc2cn1 | c1cn2ncnc2cn1 | C1C[NH]CC[NH]1.c1ccccc1.c1cn2ncnc2cn1 | HBr | CC(C)O.C(C)OCC | 95 | 8 | Brc1ncc(Br)n2ncnc12.CC(C)N1CCN(c2ccc(N)cc2)CC1>CC(C)O.C(C)OCC>CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2bd9f6e839c04a6b81426dc4856243ba | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cn2)CC1.CC1(C)OB(c2coc(C(N)=O)c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>>CC(C)N1CCN(c2ccc(Nc3ncc(-c4coc(C(N)=O)c4)n4ncnc34)cc2)CC1 | C(=O)([O-])[O-].[Na+].[Na+].CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.BrC1=CN=C(C=2N1N=CN2)NC=2C=NC(=CC2)N2CCN(CC2)C(C)C.CC1(OB(OC1(C)C)C=1C=C(OC1)C(=O)N)C>>C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(OC1)C(=O)N)N=CN2 | Br[c:16]1[cH:15][n:14][c:13]([NH:12][c:11]2[cH:10][cH:9][c:8]([N:7]3[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:33][CH2:32]3)n[cH:30]2)[c:29]2[n:25]1[n:26][cH:27][n:28]2.CC1(C)OB([c:17]2[cH:18][o:19][c:20]([C:21]([NH2:22])=[O:23])[cH:24]2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)c[cH:31]2)CC1>>[CH3:1][... | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cn2)CC1.CC1(C)OB(c2coc(C(N)=O)c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1 | CC(C)N1CCN(c2ccc(Nc3ncc(-c4coc(C(N)=O)c4)n4ncnc34)cc2)CC1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1 | C-C Coupling | OtherReaction | bf6d5b28da7df61f8a2a600f966a0396dfa36c38592da56b1b64fe7f4f86e80c | 96e5f3628c1bd4659dd3e9821904115decf673d0e8e42bb7900b7f521b084c51 | c1nc2c(Nc3ccc(N4CCNCC4)cc3)ncc(-c3ccoc3)n2n1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](-[#7:5]-[c:6]2:[c:7]:[c:8]:[c;H0;D3;+0:9](-[#7:10](-[C:11])-[C:12]):n:[cH;D2;+0:13]:2):[c:14]2:[#7;a:15]:[c:16]:[#7;a:17]:[#7;a:18]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:19]2:[c:20]:[#8;a:21]:[c:22](-[C:23](-[N;D1;H2:24])=[O;D1;H0:25]):[c:26]:2)-O-C-1(-C)-C.C-N1-C-C-N(-c2:[cH;D2;+0:27]:c... | null | [] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4, using 5-bromo-N-(6-(4-isopropylpiperazin-1-yl)pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-amine (80 mg, 0.21 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-furan-2-carboxylic acid amide (101 mg, 0.42 mmol), and Pd(PPh3)4 (62 mg,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amide.Secondary amine.Tertiary amine.Tertiary amine.Boronic ester | null | c1ccncc1.c1cn2ncnc2cn1.B1OCCO1.c1ccoc1.C1CNCCN1.c1ccccc1.c1ccsc1.c1cn2ncnc2cn1 | c1ccccc1.c1ccoc1.c1cn2ncnc2cn1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccoc1.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1 | null | null | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cn2)CC1.CC1(C)OB(c2coc(C(N)=O)c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1>CC(C)N1CC... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d1c0d6110ae46b5bac3913ab9dccf45 | CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccnc(CO)c4)n4ncnc34)cc2)CC1.CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cn2)CC1>>CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccnc(CO)c4)n4ncnc34)cn2)CC1 | C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C1=CC(=NC=C1)CO)N=CN2.BrC1=CN=C(C=2N1N=CN2)NC=2C=NC(=CC2)N2CCN(CC2)C(C)C>>C(C)(C)N1CCN(CC1)C1=CC=C(C=N1)NC=1C=2N(C(=CN1)C1=CC(=NC=C1)CO)N=CN2 | CC(C)N1CCN(c2ccc(N[c:13]3[n:14][cH:15][c:16](-[c:17]4[cH:18][cH:19][n:20][c:21]([CH2:22][OH:23])[cH:24]4)[n:25]4[n:26][cH:27][n:28][c:29]34)cc2)CC1.Brc1cnc([NH:12][c:11]2[cH:10][cH:9][c:8]([N:7]3[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:33][CH2:32]3)[n:31][cH:30]2)c2ncnn12>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2... | CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccnc(CO)c4)n4ncnc34)cc2)CC1.CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cn2)CC1 | CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccnc(CO)c4)n4ncnc34)cn2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d1da154872dac0258a7b32b30ccf643eba379743c3f0dca8db1ce5b9f2f57fb1 | 7d31f47e5761ed6e1805ce0becec02c3b3cb1ec75262e81cbdbb96933cfa3652 | c1cc(-c2cnc(Nc3ccc(N4CCNCC4)nc3)c3ncnn23)ccn1 | Br-c1:c:n:c(-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]):c2:n:c:n:n:1:2.C-C(-C)-N1-C-C-N(-c2:c:c:c(-N-[c;H0;D3;+0:7]3:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]4:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:4:3):c:c:2)-C-C-1>>[c:3]:[c:2](-[NH;D2;+0:1]-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]2:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:2:... | null | [] | null | null | null | null | This compound may be prepared using the methods as described for Compound 83, using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[6-(4-isopropylpiperazin-1-yl)pyridin-3-yl]amine in Step 4. LCMS: Rt=0.71 min (95%), m/z (ESI) 446 (M+H)+.
Conditions: See reaction.notes.procedure_details.
Workup: This compound may be prepa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine.Secondary amine.Tertiary amine.Tertiary amine | Secondary amine | C1CNCCN1.c1ccccc1.c1cn2ncnc2cn1.c1cn2ncnc2cn1 | c1cn2ncnc2cn1 | C1C[NH]CC[NH]1.c1ccncc1.c1ccncc1.c1cn2ncnc2cn1 | HBr | null | null | null | CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccnc(CO)c4)n4ncnc34)cc2)CC1.CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cn2)CC1>>CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccnc(CO)c4)n4ncnc34)cn2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-66a7e911dae54a91aadb01fdc0782deb | CC(C)I.O=[N+]([O-])c1ccc(C2CCNCC2)cc1>>CC(C)N1CCC(c2ccc([N+](=O)[O-])cc2)CC1 | [N+](=O)([O-])C1=CC=C(C=C1)C1CCNCC1.C(=O)([O-])[O-].[K+].[K+].IC(C)C>>C(C)(C)N1CCC(CC1)C1=CC=C(C=C1)[N+](=O)[O-] | I[CH:2]([CH3:1])[CH3:3].[NH:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[CH2:17][CH2:18]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[CH2:17][CH2:18]1 | CC(C)I.O=[N+]([O-])c1ccc(C2CCNCC2)cc1 | CC(C)N1CCC(c2ccc([N+](=O)[O-])cc2)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e607f8be86144f88f0e003ba760672ae287bda7930358cc9b18df3f78aaa9c0b | fb63ba09935e18320be03869002f6d5d0f0321fe7dbcd94a5ae956c3effd182d | c1ccc(C2CCNCC2)cc1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3])-[C:7]-[C:8] | 99.8 | [{"value": 99.8, "product": "C(C)(C)N1CCC(CC1)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-(4-Nitrophenyl)piperidine (250 mg, 1.21 mmol), K2CO3 (170 mg, 1.21 mmol) and 2-iodopropane (240 μL, 2.4 mmol) are stirred in acetonitrile (3 mL) in a sealed tube at 120° C. for 45 min. The mixture is cooled and the solvent removed under reduced pressure. The residue is partitioned between DCM (20 mL) and water (5 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | HI | C(C)#N | null | null | CC(C)I.O=[N+]([O-])c1ccc(C2CCNCC2)cc1>C(C)#N>CC(C)N1CCC(c2ccc([N+](=O)[O-])cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-47beca92f7bf46d2831f9c086d6c8527 | CC(C)N1CCC(c2ccc([N+](=O)[O-])cc2)CC1>>CC(C)N1CCC(c2ccc(N)cc2)CC1 | NN.C(C)(C)N1CCC(CC1)C1=CC=C(C=C1)[N+](=O)[O-]>>C(C)(C)N1CCC(CC1)C1=CC=C(C=C1)N | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]([CH:7]2[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:16][CH2:15]2)[cH:14][cH:13]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:13][cH:14]2)[CH2:15][CH2:16]1 | CC(C)N1CCC(c2ccc([N+](=O)[O-])cc2)CC1 | CC(C)N1CCC(c2ccc(N)cc2)CC1 | null | [Pd] | CCO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(C2CCNCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 72.2 | [{"value": 72.2, "product": "C(C)(C)N1CCC(CC1)C1=CC=C(C=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Hydrazine (35% by weight in water, 0.67 mL, 7.2 mmol) and 10% Pd/C (38 mg, 0.03 mmol) are added to a solution of 1-isopropyl-4-(4-nitrophenyl)piperidine (180 mg, 0.72 mmol) in EtOH (10 mL) and the mixture is heated at reflux for 3 h. After cooling, the mixture is filtered through celite and the solvent evaporated. The ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1CC[NH]CC1.c1ccccc1 | Other | [Pd].CCO | null | null | CC(C)N1CCC(c2ccc([N+](=O)[O-])cc2)CC1>[Pd].CCO>CC(C)N1CCC(c2ccc(N)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e23b0e2df6e24238abf41bf5301133be | Brc1ncc(Br)n2ncnc12.CC(C)N1CCC(c2ccc(N)cc2)CC1>>CC(C)N1CCC(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1 | C(C)(C)N(C(C)C)CC.C(C)(C)N1CCC(CC1)C1=CC=C(C=C1)N.BrC1=CN=C(C=2N1N=CN2)Br>>BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)C2CCN(CC2)C(C)C | Br[c:13]1[n:14][cH:15][c:16]([Br:17])[n:18]2[n:19][cH:20][n:21][c:22]12.[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:23][cH:24]2)[CH2:25][CH2:26]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][c:11]([NH:12][c:13]3[n:14][cH:15][c:16]([Br:17])[n:18]4[n:19... | Brc1ncc(Br)n2ncnc12.CC(C)N1CCC(c2ccc(N)cc2)CC1 | CC(C)N1CCC(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1 | null | null | CC(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | aecfb0ede2c5d7901fea69101287828edf21f7a6e48b6ff83fe43de0688f1ef1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn2ncnc2c(Nc2ccc(C3CCNCC3)cc2)n1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | null | [] | null | null | null | null | N,N-Diisopropylethylamine (200 μL, 1.2 mmol) is added to a mixture of 4-(1-isopropylpiperidin-4-yl)phenylamine (220 mg, 1.0 mmol) and 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (280 mg, 1.0 mmol) in iPrOH (5 mL) and heated at reflux for 48 h. The mixture is cooled and the solvent evaporated under reduced pressure to af... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cn2ncnc2cn1 | c1cn2ncnc2cn1 | C1CC[NH]CC1.c1ccccc1.c1cn2ncnc2cn1 | HBr | CC(C)O | null | null | Brc1ncc(Br)n2ncnc12.CC(C)N1CCC(c2ccc(N)cc2)CC1>CC(C)O>CC(C)N1CCC(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d3d356812b1f43bf9733b56ece81d4c4 | CC(C)(C)OC(=O)N1CCNC(=O)C1.Nc1ccc(I)cc1>>CC(C)(C)OC(=O)N1CCN(c2ccc(N)cc2)C(=O)C1 | IC1=CC=C(N)C=C1.C(C)(C)(C)OC(=O)N1CC(NCC1)=O.C(=O)([O-])[O-].[K+].[K+]>>C(C)(C)(C)OC(=O)N1CC(N(CC1)C1=CC=C(C=C1)N)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][C:19](=[O:20])[CH2:21]1.I[c:12]1[cH:13][cH:14][c:15]([NH2:16])[cH:17][cH:18]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([NH2:16])[cH:17][cH:18]2)[C:19](=[O:20])[CH2:21]1 | CC(C)(C)OC(=O)N1CCNC(=O)C1.Nc1ccc(I)cc1 | CC(C)(C)OC(=O)N1CCN(c2ccc(N)cc2)C(=O)C1 | null | [Cu]I | O1CCOCC1 | Heteroatom Alkylation and Arylation | Goldberg coupling | 5cf9fe2d19ef8ad0958a3c8d70022b236c24bed4db0b46e16406f2c36d7c335f | e3642f27d4c4bc101b8817e43c6aa5a22f60531030ee51c1c76056fd17c8df37 | O=C1CNCCN1c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[O;D1;H0:6]=[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 87 | [{"value": 87.0, "product": "C(C)(C)(C)OC(=O)N1CC(N(CC1)C1=CC=C(C=C1)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.6, "product": "C(C)(C)(C)OC(=O)N1CC(N(CC1)C1=CC=C(C=C1)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 119 | CELSIUS | null | null | A suspension of p-iodo-aniline (918 mg, 4.8 mmol), 3-oxo-piperazine-1-carboxylic acid tert-butyl ester (960 mg, 4.2 mmol) (1R,2R)-cyclohexane-1,2-diamine (0.05 mL, 0.42 mmol), copper (I) iodide (14.9 mg, 0.0042 mmol) and K2CO3 (1.19 g, 2.04 mmol) in dioxane (4 mL), is purged with nitrogen for 5 min in a reaction tube. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Tertiary amide | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HI | [Cu]I.O1CCOCC1 | 119 | null | CC(C)(C)OC(=O)N1CCNC(=O)C1.Nc1ccc(I)cc1>[Cu]I.O1CCOCC1>CC(C)(C)OC(=O)N1CCN(c2ccc(N)cc2)C(=O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-656a55838efe46668d7934a03825cb9b | Brc1ncc(Br)n2ncnc12.CC(C)(C)OC(=O)N1CCN(c2ccc(N)cc2)C(=O)C1>>CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)C(=O)C1 | C(C)N(C(C)C)C(C)C.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.BrC1=CN=C(C=2N1N=CN2)Br.C(C)(C)(C)OC(=O)N1CC(N(CC1)C1=CC=C(C=C1)N)=O>>C(C)(C)(C)OC(=O)N1CC(N(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)Br)N=CN2)=O | Br[c:17]1[n:18][cH:19][c:20]([Br:21])[n:22]2[n:23][cH:24][n:25][c:26]12.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([NH2:16])[cH:27][cH:28]2)[C:29](=[O:30])[CH2:31]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH... | Brc1ncc(Br)n2ncnc12.CC(C)(C)OC(=O)N1CCN(c2ccc(N)cc2)C(=O)C1 | CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)C(=O)C1 | null | null | CC(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | aecfb0ede2c5d7901fea69101287828edf21f7a6e48b6ff83fe43de0688f1ef1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1CNCCN1c1ccc(Nc2nccn3ncnc23)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 51.6 | [{"value": 51.0, "product": "C(C)(C)(C)OC(=O)N1CC(N(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)Br)N=CN2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.6, "product": "C(C)(C)(C)OC(=O)N1CC(N(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)Br)N=CN2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 1, using 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (0.283 g, 1.00 mmol), 4-(4-amino-phenyl)-3-oxo-piperazine-1-carboxylic acid ter-t-butyl ester (0.300 g, 1.00 mmol) and N-ethyldiisopropyl-amine (0.20 mL, 1.02 mmol) in 2-propanol (1 mL). Pur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cn2ncnc2cn1 | c1cn2ncnc2cn1 | C1C[NH]CC[NH]1.c1ccccc1.c1cn2ncnc2cn1 | HBr | CC(C)O | null | null | Brc1ncc(Br)n2ncnc12.CC(C)(C)OC(=O)N1CCN(c2ccc(N)cc2)C(=O)C1>CC(C)O>CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)C(=O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-80745bb0fef4445eb6ea2a08f0aacb4d | CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)C(=O)C1>>O=C1CNCCN1c1ccc(Nc2ncc(Br)n3ncnc23)cc1 | C(C)(C)(C)OC(=O)N1CC(N(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)Br)N=CN2)=O.C(=O)(C(F)(F)F)O>>BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2C(CNCC2)=O | CC(C)(C)OC(=O)[N:4]1[CH2:3][C:2](=[O:1])[N:7]([c:8]2[cH:9][cH:10][c:11]([NH:12][c:13]3[n:14][cH:15][c:16]([Br:17])[n:18]4[n:19][cH:20][n:21][c:22]34)[cH:23][cH:24]2)[CH2:6][CH2:5]1>>[O:1]=[C:2]1[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[c:8]1[cH:9][cH:10][c:11]([NH:12][c:13]2[n:14][cH:15][c:16]([Br:17])[n:18]3[n:19][cH:20][n:21... | CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)C(=O)C1 | O=C1CNCCN1c1ccc(Nc2ncc(Br)n3ncnc23)cc1 | null | null | C(Cl)Cl.C(=O)(O)[O-].[Na+] | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C1CNCCN1c1ccc(Nc2nccn3ncnc23)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5](-[c:6])-[C:7]-[C:8]-1>>[O;D1;H0:4]=[C:3]1-[C:2]-[NH;D2;+0:1]-[C:8]-[C:7]-[#7:5]-1-[c:6] | 78 | [{"value": 78.0, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2C(CNCC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2C(CNCC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-[4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-phenyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester (0.252 mg, 0.6 mmol) in 2:1 DCM:TFA (4.8 mL) is stirred for 1 hour at room temperature. The mixture is then diluted with DCM and basified with sat. NaHCO3. The aqueous layer is extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1.c1ccccc1.c1cn2ncnc2cn1 | HO- | C(Cl)Cl.C(=O)(O)[O-].[Na+] | null | null | CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)C(=O)C1>C(Cl)Cl.C(=O)(O)[O-].[Na+]>O=C1CNCCN1c1ccc(Nc2ncc(Br)n3ncnc23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-21d7e71ccb9b49acb3c3525c5cab7017 | O=C1CNCCN1c1ccc(Nc2ncc(Br)n3ncnc23)cc1.c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3cn[nH]c3)n2n1>>O=C1CNCCN1c1ccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)cc1 | CC(C)(C)[O-].[Na+].N1(CCOCC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=NNC1)N=CN2.BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2C(CNCC2)=O>>N1N=CC(=C1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2C(CNCC2)=O | Brc1cnc(Nc2c[cH:9][c:8]([N:7]3[C:2](=[O:1])[CH2:3][NH:4][CH2:5][CH2:6]3)[cH:28]c2)c2ncnn12.c1c(N2CCOCC2)c[cH:27][c:11]([NH:12][c:13]2[n:14][cH:15][c:16](-[c:17]3[cH:18][n:19][nH:20][cH:21]3)[n:22]3[n:23][cH:24][n:25][c:26]23)[cH:10]1>>[O:1]=[C:2]1[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[c:8]1[cH:9][cH:10][c:11]([NH:12][c:13]2... | O=C1CNCCN1c1ccc(Nc2ncc(Br)n3ncnc23)cc1.c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3cn[nH]c3)n2n1 | O=C1CNCCN1c1ccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CN(C)C=O.O | Miscellaneous | OtherReaction | 86ecf812006a71792fe0a5822d3580759e0bfe8f15868886516d1b5aead83a91 | 5e679d678442c10fe854b5580e44307cb1ba209a72c7b73f1ab7c0561ae39bd8 | O=C1CNCCN1c1ccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)cc1 | Br-c1:c:n:c(-N-c2:c:[cH;D2;+0:1]:[c:2](-[#7:3]-[C:4]=[O;D1;H0:5]):[cH;D2;+0:6]:c:2):c2:n:c:n:n:1:2.[#7:7]-[c:8]1:[cH;D2;+0:9]:c:c(-N2-C-C-O-C-C-2):c:[cH;D2;+0:10]:1>>[#7:7]-[c:8]1:[cH;D2;+0:9]:[cH;D2;+0:6]:[c:2](-[#7:3]-[C:4]=[O;D1;H0:5]):[cH;D2;+0:1]:[cH;D2;+0:10]:1 | 19 | [{"value": 19.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 1, step 5 using 1-[4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-phenyl]-piperazin-2-one (70 mg, 0.18 mmol) 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (64 mg, 0.33 mmol), Pd(PPh3)4 (21 mg, 18 μmol) and NaOtBu (70 mg, 0.72 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Secondary amine.Tertiary amine | null | c1ccccc1.c1cn2ncnc2cn1.c1ccccc1.C1COCCN1 | c1ccccc1 | C1C[NH]CCN1.c1ccccc1.c1cn[nH]c1.c1cn2ncnc2cn1 | HBr | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C)C=O.O | null | null | O=C1CNCCN1c1ccc(Nc2ncc(Br)n3ncnc23)cc1.c1nc2c(Nc3ccc(N4CCOCC4)cc3)ncc(-c3cn[nH]c3)n2n1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C)C=O.O>O=C1CNCCN1c1ccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3854d07172e940f88e508a0d34f2519e | CC(C)(C)N1CCNCC1.O=[N+]([O-])c1ccc(F)cc1>>CC(C)(C)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1.N | FC1=CC=C(C=C1)[N+](=O)[O-].C(C)(C)(C)N1CCNCC1.C(=O)([O-])[O-].[K+].[K+]>>N.C(C)(C)(C)N1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-] | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]1[CH2:6][CH2:7][NH:8][CH2:18][CH2:19]1.F[c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1.[NH3:20] | CC(C)(C)N1CCNCC1.O=[N+]([O-])c1ccc(F)cc1 | CC(C)(C)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1.N | null | null | O1CCOCC1 | Functional Group Interconversion | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | c6c38d29142a1aca5d86f02d4b0c2562460ca1aec33aa213f11cd4062c6e7363 | 39ece5c8e1ec3e350cfadd8e37bb010493b934313e1cd5367f16de670d62b5af | c1ccc(N2CCNCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 118.5 | [{"value": 55.4, "product": "C(C)(C)(C)N1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 118.5, "product": "C(C)(C)(C)N1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 8 | HOUR | To a solution of 1-fluoro-4-nitro-benzene (314 mg, 2.23 mmol) and 4-tert-butyl-piperazine (1 g, 3.34 mmol) in dioxane (15 mL) is added K2CO3 (1.65 mg, 11.9 mmol) and the reaction is stirred at 130° C. overnight. The solvent is evaporated under vacuum and the residue is partitioned between ethyl acetate and water. The o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | null | O1CCOCC1 | 130 | 8 | CC(C)(C)N1CCNCC1.O=[N+]([O-])c1ccc(F)cc1>O1CCOCC1>CC(C)(C)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1.N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fbaea089ba5241909d095e7297b4658b | CC(C)(C)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1>>CC(C)(C)N1CCN(c2ccc(N)cc2)CC1 | C(C)(C)(C)N1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-].O.O.[Sn](Cl)Cl.Cl>>C(C)(C)(C)N1CCN(CC1)C1=CC=C(C=C1)N | O=[N+:13]([O-])[c:12]1[cH:11][cH:10][c:9]([N:8]2[CH2:7][CH2:6][N:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:17][CH2:16]2)[cH:15][cH:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:14][cH:15]2)[CH2:16][CH2:17]1 | CC(C)(C)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1 | CC(C)(C)N1CCN(c2ccc(N)cc2)CC1 | null | null | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCNCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 100 | [{"value": 99.0, "product": "C(C)(C)(C)N1CCN(CC1)C1=CC=C(C=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.0, "product": "C(C)(C)(C)N1CCN(CC1)C1=CC=C(C=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 8 | HOUR | 1-tert-Butyl-4-(4-nitro-phenyl)-piperazine (348 mg, 1.32 mmol) is dissolved in MeOH (10 mL) and tin (II) dichloride dihydrate (1.08 g, 4.79 mmol) is added. The mixture is cooled using a water bath and conc. HCl is added (3 mL). The reaction is stirred at 40° C. overnight. After removing the methanol, the resultant solu... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | CO | 40 | 8 | CC(C)(C)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1>CO>CC(C)(C)N1CCN(c2ccc(N)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e039fcd201442198ed4aec7b55f7875 | Brc1ncc(Br)n2ncnc12.CC(C)(C)N1CCN(c2ccc(N)cc2)CC1>>CC(C)(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1 | C(C)N(C(C)C)C(C)C.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.BrC1=CN=C(C=2N1N=CN2)Br.C(C)(C)(C)N1CCN(CC1)C1=CC=C(C=C1)N>>BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCN(CC2)C(C)(C)C | Br[c:14]1[n:15][cH:16][c:17]([Br:18])[n:19]2[n:20][cH:21][n:22][c:23]12.[CH3:1][C:2]([CH3:3])([CH3:4])[N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:24][cH:25]2)[CH2:26][CH2:27]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([NH:13][c:14]3[n:15][cH:16][c:17]([Br:... | Brc1ncc(Br)n2ncnc12.CC(C)(C)N1CCN(c2ccc(N)cc2)CC1 | CC(C)(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1 | null | null | CC(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | aecfb0ede2c5d7901fea69101287828edf21f7a6e48b6ff83fe43de0688f1ef1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cn2ncnc2c(Nc2ccc(N3CCNCC3)cc2)n1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 92.4 | [{"value": 92.0, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCN(CC2)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.4, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCN(CC2)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 1, using 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (0.308 g, 1.107 mmol), 4-(4-tert-butyl-piperazin-1-yl)-phenylamine (0.310 g, 1.33 mmol) and N-ethyldiisopropyl-amine (0.289 mL, 1.66 mmol) in 2-propanol (5 mL). The reaction mixture is parti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cn2ncnc2cn1 | c1cn2ncnc2cn1 | C1C[NH]CC[NH]1.c1ccccc1.c1cn2ncnc2cn1 | HBr | CC(C)O | null | null | Brc1ncc(Br)n2ncnc12.CC(C)(C)N1CCN(c2ccc(N)cc2)CC1>CC(C)O>CC(C)(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-792bf973e1ed4f4098679685b4aba99b | CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)C(=O)C1.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C>>CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3ncc(-c4ccc5c(c4)CNC5=O)n4ncnc34)cc2)C(=O)C1 | CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.CC1(OB(OC1(C)C)C=1C=C2CNC(C2=CC1)=O)C.C(=O)([O-])[O-].[Na+].[Na+].C(C)(C)(C)OC(=O)N1CC(N(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)Br)N=CN2)=O>>C(C)(C)(C)OC(=O)N1CC(N(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C3CNC(C3=CC1)=O)N=CN2)=O | Br[c:20]1[cH:19][n:18][c:17]([NH:16][c:15]2[cH:14][cH:13][c:12]([N:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:40][C:38]3=[O:39])[cH:37][cH:36]2)[c:35]2[n:31]1[n:32][cH:33][n:34]2.CC1(C)OB([c:21]2[cH:22][cH:23][c:24]3[c:25]([cH:26]2)[CH2:27][NH:28][C:29]3=[O:30])OC1(C)C>>[CH3:1][C:2](... | CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)C(=O)C1.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C | CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3ncc(-c4ccc5c(c4)CNC5=O)n4ncnc34)cc2)C(=O)C1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1.C1(=CC=CC=C1)C.[Cl-].[Na+].O | C-C Coupling | Suzuki coupling with boronic esters | 0e514a9992c96da29f2ec2414679fb7906a3f635b15b1ade3e33600ae6778418 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | O=C1NCc2cc(-c3cnc(Nc4ccc(N5CCNCC5=O)cc4)c4ncnn34)ccc21 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-O-C-1(-C)-C>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1):[c:13]:[c:14] | 47 | [{"value": 47.0, "product": "C(C)(C)(C)OC(=O)N1CC(N(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C3CNC(C3=CC1)=O)N=CN2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.2, "product": "C(C)(C)(C)OC(=O)N1CC(N(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C3CNC(C3=CC1)=O)N=CN2)=O", "details": "CALCULATEDPERCENTYIELD", "... | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4, using 4-[4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-phenyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester (115 mg, 0.24 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one (92 mg, 0.35 mmol), a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1cn2ncnc2cn1.B1OCCO1.c1ccc2c(c1)CNC2 | c1ccc2c(c1)CNC2.c1cn2ncnc2cn1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CNC2.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C1(=CC=CC=C1)C.[Cl-].[Na+].O | null | null | CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)C(=O)C1.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C1(=CC=CC=C1)C.[Cl-].[Na+].O>CC(C)(C)OC(=O)N1CCN... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3a63ddd80d1743edae2443277d01f2d4 | CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3ncc(-c4ccc5c(c4)CNC5=O)n4ncnc34)cc2)C(=O)C1>>O=C1NCc2cc(-c3cnc(Nc4ccc(N5CCNCC5=O)cc4)c4ncnn34)ccc21 | C(C)(C)(C)OC(=O)N1CC(N(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C3CNC(C3=CC1)=O)N=CN2)=O.C(=O)(C(F)(F)F)O>>O=C1N(CCNC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C3CNC(C3=CC1)=O)N=CN2 | CC(C)(C)OC(=O)[N:20]1[CH2:19][CH2:18][N:17]([c:16]2[cH:15][cH:14][c:13]([NH:12][c:11]3[n:10][cH:9][c:8](-[c:7]4[cH:6][c:5]5[c:33]([cH:32][cH:31]4)[C:2](=[O:1])[NH:3][CH2:4]5)[n:30]4[c:26]3[n:27][cH:28][n:29]4)[cH:25][cH:24]2)[C:22](=[O:23])[CH2:21]1>>[O:1]=[C:2]1[NH:3][CH2:4][c:5]2[cH:6][c:7](-[c:8]3[cH:9][n:10][c:11](... | CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3ncc(-c4ccc5c(c4)CNC5=O)n4ncnc34)cc2)C(=O)C1 | O=C1NCc2cc(-c3cnc(Nc4ccc(N5CCNCC5=O)cc4)c4ncnn34)ccc21 | null | null | C(Cl)Cl.C(=O)(O)[O-].[Na+] | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C1NCc2cc(-c3cnc(Nc4ccc(N5CCNCC5=O)cc4)c4ncnn34)ccc21 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4](-[c:5])-[C:6](=[O;D1;H0:7])-[C:8]-1>>[O;D1;H0:7]=[C:6]1-[C:8]-[NH;D2;+0:1]-[C:2]-[C:3]-[#7:4]-1-[c:5] | 86.3 | [{"value": 86.0, "product": "O=C1N(CCNC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C3CNC(C3=CC1)=O)N=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.3, "product": "O=C1N(CCNC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C3CNC(C3=CC1)=O)N=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-oxo-4-{4-[5-(1-oxo-2,3-dihydro-1H-isoindol-5-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester (59 mg, 0.1 mmol) in 3:1 DCM:TFA (1.2 mL) is stirred at room temperature for 1 hour. The reaction mixture is diluted with DCM and basified with sat. NaHCO3. The... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccc2c(c1)CNC2.c1ccccc1.C1C[NH]CCN1.c1cn2ncnc2cn1 | HO- | C(Cl)Cl.C(=O)(O)[O-].[Na+] | null | null | CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3ncc(-c4ccc5c(c4)CNC5=O)n4ncnc34)cc2)C(=O)C1>C(Cl)Cl.C(=O)(O)[O-].[Na+]>O=C1NCc2cc(-c3cnc(Nc4ccc(N5CCNCC5=O)cc4)c4ncnn34)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3d0cc6449da24f45998160c2fbd1552d | CN(C)C=O.O=C(O)c1c(F)cc(Br)cc1F>>COC(=O)c1c(F)cc(Br)cc1F | Cl.S(=O)(Cl)Cl.CN(C)C=O.BrC1=CC(=C(C(=O)O)C(=C1)F)F>>COC(C1=C(C=C(C=C1F)Br)F)=O | CN(C=O)[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[c:6]([F:7])[cH:8][c:9]([Br:10])[cH:11][c:12]1[F:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([F:7])[cH:8][c:9]([Br:10])[cH:11][c:12]1[F:13] | CN(C)C=O.O=C(O)c1c(F)cc(Br)cc1F | COC(=O)c1c(F)cc(Br)cc1F | null | null | C(Cl)Cl.CO | Heteroatom Alkylation and Arylation | O-methylation | c9172060953e4f6c47363a85681e8adf6b8a08eda11980515725076232558272 | 897317edf82e08b628c69c2b6ae6e330cef34fadcc7a095baba8a1e1a8ad34d6 | c1ccccc1 | C-N(-[CH3;D1;+0:1])-C=O.[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | null | [] | null | null | 2.5 | HOUR | To a suspension of 4-Bromo-2,6-difluoro-benzoic acid (5 g, 21 mmol) in DCM (10 mL) is added thionyl chloride (15 mL) and DMF (0.5 mL). The mixture is stirred at room temperature for 2.5 h. It is then cooled to 0° C. and MeOH (20 mL) is added carefully causing vigorous HCl evolution. After stirring for an additional 0.5... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide | Ester | null | null | c1ccccc1 | HO- | C(Cl)Cl.CO | null | 2.5 | CN(C)C=O.O=C(O)c1c(F)cc(Br)cc1F>C(Cl)Cl.CO>COC(=O)c1c(F)cc(Br)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2cbdcdb2a20b4923b72160aca7919a86 | COC(=O)c1c(F)cc(Br)cc1F.C[N+](=O)[O-]>>COC(=O)c1c(F)cc(Br)cc1C[N+](=O)[O-] | COC(C1=C(C=C(C=C1F)Br)F)=O.[N+](=O)([O-])C.[H-].[Na+].[O-]S(=O)(=O)[O-].[Mg+2]>>COC(C1=C(C=C(C=C1C[N+](=O)[O-])Br)F)=O | F[c:12]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:6]([F:7])[cH:8][c:9]([Br:10])[cH:11]1.[CH3:13][N+:14](=[O:15])[O-:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([F:7])[cH:8][c:9]([Br:10])[cH:11][c:12]1[CH2:13][N+:14](=[O:15])[O-:16] | COC(=O)c1c(F)cc(Br)cc1F.C[N+](=O)[O-] | COC(=O)c1c(F)cc(Br)cc1C[N+](=O)[O-] | null | null | CS(=O)C | C-C Coupling | OtherReaction | cd8b5052688b7919a207207149d12f6b6cbbc3b607c9eb9fde3a8ff930782506 | 5dcf4124513b16cd3f4b18ce2434242a66d25ddc466fbc0674492d31d46556fb | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8]):[c:9].[CH3;D1;+0:10]-[#7;+:11](-[O;-;D1;H0:12])=[O;D1;H0:13]>>[C;D1;H3:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[CH2;D2;+0:10]-[#7;+:11](-[O;-;D1;H0:12])=[O;D1;H0:13]):[c:2]:[c:3] | null | [] | null | null | 0.25 | HOUR | Nitromethane (10 mL, 169 mmol, 8 equiv.) is added cautiously to a suspension of sodium hydride (4.05 g, 169 mmol, 8 equiv.) and MgSO4 (40 g) in DMSO (100 mL) at rt and the resulting slurry is stirred for 0.25 h. To the resulting yellow slurry is added 4-bromo-2,6-difluorobenzoic acid methyl ester (5.3 g, 21 mmol) and t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitro group | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | CS(=O)C | null | 0.25 | COC(=O)c1c(F)cc(Br)cc1F.C[N+](=O)[O-]>CS(=O)C>COC(=O)c1c(F)cc(Br)cc1C[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d7a5d50cbcc84b2588b75eadef826e0e | COC(=O)c1c(F)cc(Br)cc1C[N+](=O)[O-]>>O=C1NCc2cc(Br)cc(F)c21 | N.COC(C1=C(C=C(C=C1C[N+](=O)[O-])Br)F)=O.C(=O)[O-].[NH4+]>>BrC=1C=C2CNC(C2=C(C1)F)=O | CO[C:2](=[O:1])[c:12]1[c:5]([CH2:4][N+:3](=O)[O-])[cH:6][c:7]([Br:8])[cH:9][c:10]1[F:11]>>[O:1]=[C:2]1[NH:3][CH2:4][c:5]2[cH:6][c:7]([Br:8])[cH:9][c:10]([F:11])[c:12]21 | COC(=O)c1c(F)cc(Br)cc1C[N+](=O)[O-] | O=C1NCc2cc(Br)cc(F)c21 | null | [Zn] | C(Cl)Cl.CO | Functional Group Interconversion | OtherReaction | 166d9d3d6afdc459f3b81568112cf297aeec7e6533dedd63b925cc3c46d90830 | 42f24d3b25bb26f4d7fac0ebbebf6d046ea37d400eb2e6f47c39069d069d5e9d | O=C1NCc2ccccc21 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[C:6]-[N+;H0;D3:7](=O)-[O-]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[NH;D2;+0:7]-[C:6]-[c:5]:[c:3]-1:[c:4] | null | [] | null | null | 0.3 | HOUR | Crude 4-bromo-2-fluoro-6-(nitromethyl)benzoic acid methyl ester from the previous step is dissolved in MeOH (100 mL). To this clear orange solution is added Zinc dust (3.35 g, 51.3 mmol, 3 equiv.) followed by ammonium formate (3.23 g, 51.3 mmol, 3 equiv.) which results in an exothermic reaction. After 0.3 h, 7M NH3 in ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group | Secondary amide | null | c1ccc2c(c1)CNC2 | c1ccc2c(c1)CNC2 | HO- | [Zn].C(Cl)Cl.CO | null | 0.3 | COC(=O)c1c(F)cc(Br)cc1C[N+](=O)[O-]>[Zn].C(Cl)Cl.CO>O=C1NCc2cc(Br)cc(F)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-31b3761fa2b2411d9d9313462cee3b07 | CC(C)=O.O=C1CNCCN1c1ccc(Nc2ncc(Br)n3ncnc23)cc1>>CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)C(=O)C1 | Cl.[BH3-]C#N.[Na+].BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2C(CNCC2)=O.C(C)(=O)O.CC(=O)[O-].[Na+].CC(=O)C>>BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2C(CN(CC2)C(C)C)=O | O=[C:2]([CH3:1])[CH3:3].[NH:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH:12][c:13]3[n:14][cH:15][c:16]([Br:17])[n:18]4[n:19][cH:20][n:21][c:22]34)[cH:23][cH:24]2)[C:25](=[O:26])[CH2:27]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH:12][c:13]3[n:14][cH:15][c:16]([Br:17])[n:18]4[... | CC(C)=O.O=C1CNCCN1c1ccc(Nc2ncc(Br)n3ncnc23)cc1 | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)C(=O)C1 | null | null | CO | Heteroatom Alkylation and Arylation | reductive amination | d4cc9a2a46f538d7a2ff577eac4d4531ea828578c3aec2ccd0e8c1d501914fc6 | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | O=C1CNCCN1c1ccc(Nc2nccn3ncnc23)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[O;D1;H0:4]=[C:5]1-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-[#7:10]-1-[c:11]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[N;H0;D3;+0:7]1-[C:6]-[C:5](=[O;D1;H0:4])-[#7:10](-[c:11])-[C:9]-[C:8]-1 | 25 | [{"value": 25.0, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2C(CN(CC2)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.3, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2C(CN(CC2)C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 1-[4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-phenyl]-piperazin-2-one (example 31, step 2) (180 mg, 0.47 mmol) in MeOH (4 mL) are added acetic acid (0.03 mL, 0.47 mmol), NaOAc (38 mg, 0.47 mmol) and acetone (0.2 mL, 1.18 mmol). The reaction mixture is stirred at room temperature for 1 hour the... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1cn2ncnc2cn1 | Other | CO | null | 1 | CC(C)=O.O=C1CNCCN1c1ccc(Nc2ncc(Br)n3ncnc23)cc1>CO>CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)C(=O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4aa3a42f7ba04c6ca4b3d36ee16a900e | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)C(=O)C1.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>>CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccc5c(c4)CNC5=O)n4ncnc34)cc2)C(=O)C1.N | C(=O)([O-])[O-].[Na+].[Na+].BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2C(CN(CC2)C(C)C)=O.CC1(OB(OC1(C)C)C=1C=C2CNC(C2=CC1)=O)C.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2>>N.C(C)(C)N1CC(N(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C3CNC(C3=CC1)=O)N=CN2)=O | Br[c:16]1[cH:15][n:14][c:13]([NH:12][c:11]2[cH:10][cH:9][c:8]([N:7]3[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:36][C:34]3=[O:35])[cH:33][cH:32]2)[c:31]2[n:27]1[n:28][cH:29][n:30]2.CC1(C)OB([c:17]2[cH:18][cH:19][c:20]3[c:21]([cH:22]2)[CH2:23][NH:24][C:25]3=[O:26])OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(=O)[NH2:37])c4)... | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)C(=O)C1.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1 | CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccc5c(c4)CNC5=O)n4ncnc34)cc2)C(=O)C1.N | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1.C1(=CC=CC=C1)C.[Cl-].[Na+].O | C-C Coupling | OtherReaction | d96e7a493e1619b343e6902e2f3e9ceea3531a747b8fbd8e81a720c753a845f2 | 96e5f3628c1bd4659dd3e9821904115decf673d0e8e42bb7900b7f521b084c51 | O=C1NCc2cc(-c3cnc(Nc4ccc(N5CCNCC5=O)cc4)c4ncnn34)ccc21 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-O-C-1(-C)-C.C-N1-C-C-N(-c2:c:c:c(-N-c3:n:c:c(-c4:c:s:c(-C(=O)-[NH2;D1;+0:15]):c:4):n4:n:c:n:c:3:4):c:c:2)-C-C-1>>[NH3;D0;+0:15].[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:... | 55 | [{"value": 55.0, "product": "C(C)(C)N1CC(N(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C3CNC(C3=CC1)=O)N=CN2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4, using 1-[4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-phenyl]-4-isopropyl-piperazin-2-one (40 mg, 0.09 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one (37 mg, 0.14 mmol), and Pd(PPh3)4 (31 mg, 0.02... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amide.Secondary amine.Tertiary amine.Tertiary amine.Boronic ester | null | c1cn2ncnc2cn1.B1OCCO1.c1ccc2c(c1)CNC2.C1CNCCN1.c1ccccc1.c1ccsc1.c1cn2ncnc2cn1 | c1ccc2c(c1)CNC2.c1cn2ncnc2cn1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CNC2.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C1(=CC=CC=C1)C.[Cl-].[Na+].O | null | null | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)C(=O)C1.CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C1(... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f2d8e5b64ea644f5b070681cb504cfdd | CI.COc1ccc(CBr)cc1.O=C1NCc2cc(Br)ccc21>>COc1ccc(CN2C(=O)c3ccc(Br)cc3C2(C)C)cc1 | BrC=1C=C2CNC(C2=CC1)=O.C1CCOC1.[H-].[Na+].COC1=CC=C(CBr)C=C1.IC.[NH4+].[Cl-].[H-].[Na+].[I-].C1CCOC1>>BrC=1C=C2C(N(C(C2=CC1)=O)CC1=CC=C(C=C1)OC)(C)C | I[CH3:20].Br[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22][cH:21]1.[NH:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]2[CH2:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[C:9](=[O:10])[c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]3[C:18]2([CH3:19])[CH3:20])[cH:21][cH:22]1 | CI.COc1ccc(CBr)cc1.O=C1NCc2cc(Br)ccc21 | COc1ccc(CN2C(=O)c3ccc(Br)cc3C2(C)C)cc1 | null | null | CN(C)C=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 9f5b0a1dbe0bd9f7211acdfdc653a03d59b835d4d029f835ea392c4ae188fa9a | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1c2ccccc2CN1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].I-[CH3;D1;+0:5].[O;D1;H0:6]=[C:7]1-[NH;D2;+0:8]-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12]-1>>[C;D1;H3:13]-[C;H0;D4;+0:9]1(-[CH3;D1;+0:5])-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:7](=[O;D1;H0:6])-[c:12]:[c:10]-1:[c:11] | null | [] | null | null | 4 | HOUR | A suspension of sodium hydride (130 mg, 60% dispersion in mineral oil, 3.2 mmol) and tetra-nbutylammonium iodide (243 mg, 0.68 mmol) in THF (20 mL) is stirred at rt and a solution of 5-bromo-2,3-dihydroisoindol-1-one (675 mg, 3.2 mmol) in THF (20 mL) and DMF (4 mL) is added. After 75 min 4-methoxybenzyl bromide (460 μL... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccccc1.c1ccc2c(c1)C[NH]C2 | Br-.I- | CN(C)C=O.C(C)(=O)OCC | null | 4 | CI.COc1ccc(CBr)cc1.O=C1NCc2cc(Br)ccc21>CN(C)C=O.C(C)(=O)OCC>COc1ccc(CN2C(=O)c3ccc(Br)cc3C2(C)C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3eae8be13edb415e92dc28b5f0766434 | COc1ccc(CN2C(=O)c3ccc(Br)cc3C2(C)C)cc1>>CC1(C)NC(=O)c2ccc(Br)cc21 | BrC=1C=C2C(N(C(C2=CC1)=O)CC1=CC=C(C=C1)OC)(C)C>>BrC=1C=C2C(NC(C2=CC1)=O)(C)C | COc1ccc(C[N:4]2[C:2]([CH3:1])([CH3:3])[c:13]3[c:7]([cH:8][cH:9][c:10]([Br:11])[cH:12]3)[C:5]2=[O:6])cc1>>[CH3:1][C:2]1([CH3:3])[NH:4][C:5](=[O:6])[c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][c:13]21 | COc1ccc(CN2C(=O)c3ccc(Br)cc3C2(C)C)cc1 | CC1(C)NC(=O)c2ccc(Br)cc21 | null | null | C(C)#N.O.C(C)(=O)OCC | Reduction | Hydrogenolysis of tertiary amines | e7566f8128c1a44807aeb07dea55552bf419d8005020ba5dabdef40b36726993 | 3da95258cd6a6ca6a5fed40d269eda3c543e9e67e5f33234974139a39c57d43d | O=C1NCc2ccccc21 | C-O-c1:c:c:c(-C-[N;H0;D3;+0:1]2-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]-[C:6]-2(-[C;D1;H3:7])-[C;D1;H3:8]):c:c:1>>[C;D1;H3:7]-[C:6]1(-[C;D1;H3:8])-[NH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]-1 | 86 | [{"value": 86.0, "product": "BrC=1C=C2C(NC(C2=CC1)=O)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-bromo-2-(4-methoxybenzyl)-3,3-dimethyl-2,3-dihydroisoindol-1-one (640 mg, 1.78 mmol) and ceric ammonium nitrate (2.91 g, 5.33 mmol) in acetonitrile (11 mL) and water (5 mL) is stirred at 0° C. for 45 min. The solution is diluted with ethyl acetate (100 mL) and washed with brine (40 mL). The organic solv... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amide | Secondary amide | c1ccccc1.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)CNC2 | c1ccc2c(c1)CNC2 | HO- | C(C)#N.O.C(C)(=O)OCC | null | null | COc1ccc(CN2C(=O)c3ccc(Br)cc3C2(C)C)cc1>C(C)#N.O.C(C)(=O)OCC>CC1(C)NC(=O)c2ccc(Br)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-405bef0570904f9abc44789b427e7f09 | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1.CC1(C)NC(=O)c2ccc(Br)cc21>>CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccc5c(c4)C(C)(C)NC5=O)n4ncnc34)cc2)CC1 | BrC=1C=C2C(NC(C2=CC1)=O)(C)C.B([O-])[O-].BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)N2CCN(CC2)C(C)C>>C(C)(C)N1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C3C(NC(C3=CC1)=O)(C)C)N=CN2 | Br[c:16]1[cH:15][n:14][c:13]([NH:12][c:11]2[cH:10][cH:9][c:8]([N:7]3[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:37][CH2:36]3)[cH:35][cH:34]2)[c:33]2[n:29]1[n:30][cH:31][n:32]2.Br[c:17]1[cH:18][cH:19][c:20]2[c:21]([cH:22]1)[C:23]([CH3:24])([CH3:25])[NH:26][C:27]2=[O:28]>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][N:... | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1.CC1(C)NC(=O)c2ccc(Br)cc21 | CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccc5c(c4)C(C)(C)NC5=O)n4ncnc34)cc2)CC1 | null | null | null | C-C Coupling | Negishi | beec43a7e9690bedf06a3f41502760638b5f58c8f2a5cf6eff7eca2c4f053fe6 | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | O=C1NCc2cc(-c3cnc(Nc4ccc(N5CCNCC5)cc4)c4ncnn34)ccc21 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].Br-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[c:9]:[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[#7;a:14]:2:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[c:9]:[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[#7;a:14]:2:1):[c:4]:[c:5] | null | [] | null | null | null | null | 5-Bromo-3,3-dimethyl-2,3-dihydroisoindol-1-one is converted to the corresponding boronate in a fashion analogous to Intermediate 6, Step 3. This is then used to prepare the title compound from (5-bromo[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(4-isopropylpiperazin-1-yl)-phenyl]amine using methods as described for Compound... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1cn2ncnc2cn1.c1ccc2c(c1)CNC2 | c1ccc2c(c1)CNC2.c1cn2ncnc2cn1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)CNC2.c1cn2ncnc2cn1 | Br- | null | null | null | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2)CC1.CC1(C)NC(=O)c2ccc(Br)cc21>>CC(C)N1CCN(c2ccc(Nc3ncc(-c4ccc5c(c4)C(C)(C)NC5=O)n4ncnc34)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f5414befd6b43e4b8bf61b0c1b78428 | Brc1ncc(Br)n2ncnc12.COC(=O)c1ccc(N)cc1>>COC(=O)c1ccc(Nc2ncc(Br)n3ncnc23)cc1 | C(C)N(C(C)C)C(C)C.BrC1=CN=C(C=2N1N=CN2)Br.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.COC(C1=CC=C(C=C1)N)=O>>COC(C1=CC=C(C=C1)NC=1C=2N(C(=CN1)Br)N=CN2)=O | Br[c:10]1[n:11][cH:12][c:13]([Br:14])[n:15]2[n:16][cH:17][n:18][c:19]12.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:20][cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([NH:9][c:10]2[n:11][cH:12][c:13]([Br:14])[n:15]3[n:16][cH:17][n:18][c:19]23)[cH:20][cH:21]1 | Brc1ncc(Br)n2ncnc12.COC(=O)c1ccc(N)cc1 | COC(=O)c1ccc(Nc2ncc(Br)n3ncnc23)cc1 | null | null | CC(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | aecfb0ede2c5d7901fea69101287828edf21f7a6e48b6ff83fe43de0688f1ef1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccn3ncnc23)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | null | [] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 1 using 5,8-dibromo-[1,2,4]triazolo[1,5-a]pyrazine (250 mg, 0.90 mmol), 4-aminobenzoic methyl ester (163 mg, 1.08 mmol) and N-ethyldiisopropyl-amine (0.19 mL, 1.08 mmol) in 2-propanol (2.5 mL). The title compound is obtained after trituration... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cn2ncnc2cn1 | c1cn2ncnc2cn1 | c1ccccc1.c1cn2ncnc2cn1 | HBr | CC(C)O | null | null | Brc1ncc(Br)n2ncnc12.COC(=O)c1ccc(N)cc1>CC(C)O>COC(=O)c1ccc(Nc2ncc(Br)n3ncnc23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2e1ed6dc46e549f8adcab4603cc91303 | COC(=O)c1ccc(Nc2ncc(Br)n3ncnc23)cc1>>O=C(O)c1ccc(Nc2ncc(Br)n3ncnc23)cc1 | COC(C1=CC=C(C=C1)NC=1C=2N(C(=CN1)Br)N=CN2)=O.O.[OH-].[Li+].CO>>BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C(=O)O)C=C2 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([Br:13])[n:14]3[n:15][cH:16][n:17][c:18]23)[cH:19][cH:20]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]([Br:13])[n:14]3[n:15][cH:16][n:17][c:18]23)[cH:19][cH:20]1 | COC(=O)c1ccc(Nc2ncc(Br)n3ncnc23)cc1 | O=C(O)c1ccc(Nc2ncc(Br)n3ncnc23)cc1 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nccn3ncnc23)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 49 | [{"value": 49.0, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C(=O)O)C=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.7, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C(=O)O)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 4-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-benzoic acid methyl ester (460 mg, 1.32 mmol) is suspended in THF (11 mL) and a solution of lithium hydroxide monohydrate (554 mg, 13.2 mmol) in water (11 mL) is added. The reaction mixture is stirred at room temperature for 4 hours then methanol (11 mL) is added and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cn2ncnc2cn1 | Other | O.C1CCOC1 | null | 4 | COC(=O)c1ccc(Nc2ncc(Br)n3ncnc23)cc1>O.C1CCOC1>O=C(O)c1ccc(Nc2ncc(Br)n3ncnc23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b845953dd7eb40e0a2010114ce8d5640 | NCc1cccnc1.O=C(O)c1ccc(Nc2ncc(Br)n3ncnc23)cc1>>O=C(NCc1cccnc1)c1ccc(Nc2ncc(Br)n3ncnc23)cc1 | BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C(=O)O)C=C2.ON1N=NC2=C1C=CC=C2.O.C(C)N=C=NCCCN(C)C.N1=CC(=CC=C1)CN>>BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C(=O)NCC=1C=NC=CC1)C=C2 | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1.O[C:2](=[O:1])[c:11]1[cH:12][cH:13][c:14]([NH:15][c:16]2[n:17][cH:18][c:19]([Br:20])[n:21]3[n:22][cH:23][n:24][c:25]23)[cH:26][cH:27]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]([NH:15][c:16]2[n:17][cH:18][c:19]([Br:20]... | NCc1cccnc1.O=C(O)c1ccc(Nc2ncc(Br)n3ncnc23)cc1 | O=C(NCc1cccnc1)c1ccc(Nc2ncc(Br)n3ncnc23)cc1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCc1cccnc1)c1ccc(Nc2nccn3ncnc23)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]:[c:8]-[C:9]-[NH2;D1;+0:10]>>[#7;a:6]:[c:7]:[c:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 82.3 | [{"value": 82.0, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C(=O)NCC=1C=NC=CC1)C=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.3, "product": "BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C(=O)NCC=1C=NC=CC1)C=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-benzoic acid (0.230 g, 0.69 mmol), 3-hydroxybenzotriazole (0.103 g, 0.76 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrate (0.146 g, 0.76 mmol) in DMF (5 mL) and 3-picolylamine (0.077 mL, 0.76 mmol) is stirred at room temperature for 21 hours... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1.c1cn2ncnc2cn1 | HO- | CN(C)C=O | null | null | NCc1cccnc1.O=C(O)c1ccc(Nc2ncc(Br)n3ncnc23)cc1>CN(C)C=O>O=C(NCc1cccnc1)c1ccc(Nc2ncc(Br)n3ncnc23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f373c043f7f84a34a628cd9ded59a339 | CC1(C)OB(c2cn[nH]c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.O=C(NCc1cccnc1)c1ccc(Nc2ncc(Br)n3ncnc23)cc1>>N.O=C(NCc1cccnc1)c1ccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)cc1 | CC1(OB(OC1(C)C)C=1C=NNC1)C.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C(=O)NCC=1C=NC=CC1)C=C2>>N.N1N=CC(=C1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C(=O)NCC=1C=NC=CC1)C=C2 | CC1(C)OB([c:21]2[cH:22][n:23][nH:24][cH:25]2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(=O)[NH2:1])c4)n4ncnc34)cc2)CC1.Br[c:20]1[cH:19][n:18][c:17]([NH:16][c:15]2[cH:14][cH:13][c:12]([C:3](=[O:2])[NH:4][CH2:5][c:6]3[cH:7][cH:8][cH:9][n:10][cH:11]3)[cH:32][cH:31]2)[c:30]2[n:26]1[n:27][cH:28][n:29]2>>[NH3:1].[O:2]=[C:3]([NH:4]... | CC1(C)OB(c2cn[nH]c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.O=C(NCc1cccnc1)c1ccc(Nc2ncc(Br)n3ncnc23)cc1 | N.O=C(NCc1cccnc1)c1ccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1.C(=O)([O-])[O-].[K+].[K+] | C-C Coupling | OtherReaction | 5450a2db6e7305c45383870e931e62f9935b44015cf383067240af8b2a416783 | 96e5f3628c1bd4659dd3e9821904115decf673d0e8e42bb7900b7f521b084c51 | O=C(NCc1cccnc1)c1ccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[#7;a:13]:[c:14]:2)-O-C-1(-C)-C.C-N1-C-C-N(-c2:c:c:c(-N-c3:n:c:c(-c4:c:s:c(-C(=O)-[NH2;D1;+0:15]):c:4):n4:n:c:n:c:3:4):c:c:2)-C-C-1>>[#7;a:3]1:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]... | 20 | [{"value": 20.0, "product": "N1N=CC(=C1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C(=O)NCC=1C=NC=CC1)C=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4 using 4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-N-pyridin-3-ylmethyl-benzamide (100 mg, 0.24 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (93 mg, 0.48 mmol) and Pd(PPh3)4 (70 mg, 0.06 mmol) in 1.5M K2CO3 (aq... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amide.Secondary amine.Tertiary amine.Tertiary amine.Boronic ester | null | B1OCCO1.c1cn[nH]c1.C1CNCCN1.c1ccccc1.c1ccsc1.c1cn2ncnc2cn1.c1cn2ncnc2cn1 | c1cn[nH]c1.c1cn2ncnc2cn1 | c1ccncc1.c1ccccc1.c1cn[nH]c1.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(=O)([O-])[O-].[K+].[K+] | null | null | CC1(C)OB(c2cn[nH]c2)OC1(C)C.CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.O=C(NCc1cccnc1)c1ccc(Nc2ncc(Br)n3ncnc23)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(=O)([O-])[O-... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-21b1c2adf0644a34b21ca76c607e94a5 | CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.COc1cc(B(O)O)ccn1.O=C(NCc1cccnc1)c1ccc(Nc2ncc(Br)n3ncnc23)cc1>>COc1cc(-c2cnc(Nc3ccc(C(=O)NCc4cccnc4)cc3)c3ncnn23)ccn1.N | COC1=NC=CC(=C1)B(O)O.CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2.BrC1=CN=C(C=2N1N=CN2)NC2=CC=C(C(=O)NCC=1C=NC=CC1)C=C2>>N.COC1=NC=CC(=C1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C(=O)NCC=1C=NC=CC1)C=C2 | CN1CCN(c2ccc(Nc3ncc(-c4csc(C(=O)[NH2:35])c4)n4ncnc34)cc2)CC1.OB(O)[c:5]1[cH:4][c:3]([O:2][CH3:1])[n:34][cH:33][cH:32]1.Br[c:6]1[cH:7][n:8][c:9]([NH:10][c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[NH:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][n:23][cH:24]3)[cH:25][cH:26]2)[c:27]2[n:28][cH:29][n:30][n:31]12>>[CH3:1][O:2][c:3... | CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.COc1cc(B(O)O)ccn1.O=C(NCc1cccnc1)c1ccc(Nc2ncc(Br)n3ncnc23)cc1 | COc1cc(-c2cnc(Nc3ccc(C(=O)NCc4cccnc4)cc3)c3ncnn23)ccn1.N | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1.C(=O)([O-])[O-].[K+].[K+] | C-C Coupling | OtherReaction | 41d4aa0ca986d610e9fc08a0f4c103dba42089333936aa6db5645b06538ea4c0 | e56c7214f97d6930a188bbe94b3feccb44f2b9c6a54832ba0c9cbf78acce3e55 | O=C(NCc1cccnc1)c1ccc(Nc2ncc(-c3ccncc3)n3ncnc23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-N1-C-C-N(-c2:c:c:c(-N-c3:n:c:c(-c4:c:s:c(-C(=O)-[NH2;D1;+0:10]):c:4):n4:n:c:n:c:3:4):c:c:2)-C-C-1.O-B(-O)-[c;H0;D3;+0:11]1:[c:12]:[c:13]:[#7;a:14]:[c:15](-[#8:16]):[c:17]:1>>[#8:16]-[c:15]1:[#7;a:14]:[c:13]:[c:12]:[c;H0;D3;+0:11](-[c;... | 73 | [{"value": 73.0, "product": "COC1=NC=CC(=C1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C(=O)NCC=1C=NC=CC1)C=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound may be prepared using methods as described for Compound 6, step 4 using 4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-N-pyridin-3-ylmethyl-benzamide (120 mg, 0.28 mmol), 2-methoxypyridine-4-boronic acid (87 mg, 0.57 mmol) and Pd(PPh3)4 (81 mg, 0.07 mmol) in 1.5M K2CO3 (aq) (1.6 mL) and dioxane (2.9 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amide.Secondary amine.Tertiary amine.Tertiary amine.Boronic acid | null | C1CNCCN1.c1ccccc1.c1ccsc1.c1cn2ncnc2cn1.c1ccncc1.c1cn2ncnc2cn1 | c1ccncc1.c1cn2ncnc2cn1 | c1ccncc1.c1ccccc1.c1ccncc1.c1cn2ncnc2cn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(=O)([O-])[O-].[K+].[K+] | null | null | CN1CCN(c2ccc(Nc3ncc(-c4csc(C(N)=O)c4)n4ncnc34)cc2)CC1.COc1cc(B(O)O)ccn1.O=C(NCc1cccnc1)c1ccc(Nc2ncc(Br)n3ncnc23)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.C(=O)([O-])[O-].[K+].[K+... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c2f81362810d41deb825d38a2fa6e642 | COc1cc(-c2cnc(Nc3ccc(C(=O)NCc4cccnc4)cc3)c3ncnn23)ccn1>>O=C(NCc1cccnc1)c1ccc(Nc2ncc(-c3cc[nH]c(=O)c3)n3ncnc23)cc1 | COC1=NC=CC(=C1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C(=O)NCC=1C=NC=CC1)C=C2.Cl.[NH+]1=CC=CC=C1>>O=C1NC=CC(=C1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C(=O)NCC=1C=NC=CC1)C=C2 | C[O:25][c:24]1[n:23][cH:22][cH:21][c:20](-[c:19]2[cH:18][n:17][c:16]([NH:15][c:14]3[cH:13][cH:12][c:11]([C:2](=[O:1])[NH:3][CH2:4][c:5]4[cH:6][cH:7][cH:8][n:9][cH:10]4)[cH:33][cH:32]3)[c:31]3[n:27]2[n:28][cH:29][n:30]3)[cH:26]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14](... | COc1cc(-c2cnc(Nc3ccc(C(=O)NCc4cccnc4)cc3)c3ncnn23)ccn1 | O=C(NCc1cccnc1)c1ccc(Nc2ncc(-c3cc[nH]c(=O)c3)n3ncnc23)cc1 | null | null | O | Miscellaneous | OtherReaction | fb5da40428a7272a59dd461a4f5e161a7614b101c1a367e77b5ddd5b70c77e0d | 291cad8b6dfbbd2c823b5c9d45efc37a166dc3454a9f151ac48cb357f4bc155f | O=C(NCc1cccnc1)c1ccc(Nc2ncc(-c3cc[nH]c(=O)c3)n3ncnc23)cc1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[n;H0;D2;+0:7]:1>>[O;H0;D1;+0:1]=[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1 | 49 | [{"value": 49.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | A mixture of 4-[5-(2-methoxy-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino]-N-pyridin-3-ylmethyl-benzamide (71.5 mg, 0.16 mmol) and pyridinium hydrochloride (91 mg, 0.79 mmol) in water (0.5 mL) in a sealed tube is heated at 150° C. for 25 minutes. After this time the solvent is removed in vacuo. The residue is ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccncc1.c1cn2ncnc2cn1 | Other | O | 150 | null | COc1cc(-c2cnc(Nc3ccc(C(=O)NCc4cccnc4)cc3)c3ncnn23)ccn1>O>O=C(NCc1cccnc1)c1ccc(Nc2ncc(-c3cc[nH]c(=O)c3)n3ncnc23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-43a1ea37067d45fc96a9ae3ea13df240 | COc1cc([N+](=O)[O-])ccc1C(=O)O.Cc1ccc(CN)cn1>>COc1cc([N+](=O)[O-])ccc1C(=O)NCc1ccc(C)nc1 | CC1=CC=C(C=N1)CN.CN1CCOCC1.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.[B-](F)(F)(F)F.COC1=C(C(=O)O)C=CC(=C1)[N+](=O)[O-]>>COC1=C(C(=O)NCC=2C=NC(=CC2)C)C=CC(=C1)[N+](=O)[O-] | O[C:12]([c:11]1[c:3]([O:2][CH3:1])[cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][cH:10]1)=[O:13].[NH2:14][CH2:15][c:16]1[cH:17][cH:18][c:19]([CH3:20])[n:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][cH:10][c:11]1[C:12](=[O:13])[NH:14][CH2:15][c:16]1[cH:17][cH:18][c:19]([CH3:20])[n:21][cH:22]1 | COc1cc([N+](=O)[O-])ccc1C(=O)O.Cc1ccc(CN)cn1 | COc1cc([N+](=O)[O-])ccc1C(=O)NCc1ccc(C)nc1 | null | null | CN(C)C=O.C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCc1cccnc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]:[c:8]-[C:9]-[NH2;D1;+0:10]>>[#7;a:6]:[c:7]:[c:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 30 | MINUTE | 2-Methoxy-4-nitrobenzoic acid (293 mg, 1.49 mmol) is dissolved in DMF (2 mL) and 4-methylmorpholine (220 μL, 3.0 mmol) and TBTU (1.79 g, 1.7 mmol) are added. The mixture is stirred at rt for 30 min and C-(6-methylpyridin-3-yl)methylamine (400 mg, 3.27 mmol) is added. Stirring is continued at rt for 12 h. DCM (10 mL) is... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HO- | CN(C)C=O.C(Cl)Cl | null | 0.5 | COc1cc([N+](=O)[O-])ccc1C(=O)O.Cc1ccc(CN)cn1>CN(C)C=O.C(Cl)Cl>COc1cc([N+](=O)[O-])ccc1C(=O)NCc1ccc(C)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e09abf6fa88547ee8d2f16872d8b2a14 | COc1cc([N+](=O)[O-])ccc1C(=O)NCc1ccc(C)nc1>>COc1cc(N)ccc1C(=O)NCc1ccc(C)nc1 | COC1=C(C(=O)NCC=2C=NC(=CC2)C)C=CC(=C1)[N+](=O)[O-].C(=O)[O-].[NH4+]>>NC1=CC(=C(C(=O)NCC=2C=NC(=CC2)C)C=C1)OC | O=[N+:6]([O-])[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:9]([C:10](=[O:11])[NH:12][CH2:13][c:14]2[cH:15][cH:16][c:17]([CH3:18])[n:19][cH:20]2)[cH:8][cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12][CH2:13][c:14]1[cH:15][cH:16][c:17]([CH3:18])[n:19][cH:20]1 | COc1cc([N+](=O)[O-])ccc1C(=O)NCc1ccc(C)nc1 | COc1cc(N)ccc1C(=O)NCc1ccc(C)nc1 | null | [Pd] | CCO.CCOC(=O)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(NCc1cccnc1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A solution of 2-methoxy-N-(6-methylpyridin-3-yl)methyl-4-nitrobenzamide (448 mg, 1.49 mmol) in EtOH and EtOAc (8 mL each) is stirred and ammonium formate (375 mg, 6 mmol) and 10% Pd/C (100 mg) are added. The mixture is heated at reflux for 20 min, cooled, filtered through celite, the solid is washed with EtOH and the c... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccncc1 | Other | [Pd].CCO.CCOC(=O)C | null | null | COc1cc([N+](=O)[O-])ccc1C(=O)NCc1ccc(C)nc1>[Pd].CCO.CCOC(=O)C>COc1cc(N)ccc1C(=O)NCc1ccc(C)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3e583b69311444e6ac7f180eec252c3a | Brc1ncc(Br)n2ncnc12.COc1cc(N)ccc1C(=O)NCc1ccc(C)nc1>>Cc1ccc(CNC(=O)c2ccc(Nc3ncc(Br)n4ncnc34)cc2O)cn1 | BrC1=CN=C(C=2N1N=CN2)Br.NC1=CC(=C(C(=O)NCC=2C=NC(=CC2)C)C=C1)OC.C(=O)(O)[O-].[Na+].Br>>BrC1=CN=C(C=2N1N=CN2)NC2=CC(=C(C(=O)NCC=1C=NC(=CC1)C)C=C2)O | Br[c:15]1[n:16][cH:17][c:18]([Br:19])[n:20]2[n:21][cH:22][n:23][c:24]12.C[O:27][c:26]1[c:10]([C:8]([NH:7][CH2:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:29][cH:28]2)=[O:9])[cH:11][cH:12][c:13]([NH2:14])[cH:25]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([NH:14][c:15]3[n:16][cH:17][c... | Brc1ncc(Br)n2ncnc12.COc1cc(N)ccc1C(=O)NCc1ccc(C)nc1 | Cc1ccc(CNC(=O)c2ccc(Nc3ncc(Br)n4ncnc34)cc2O)cn1 | null | null | O.CC(C)O | Heteroatom Alkylation and Arylation | OtherReaction | e8830d2dc159e2698fd6973d85ee5c0f5af45e99dfb394e286d23433deb9893b | 6b24500fd64e6aa86066d0cc793af94111bb9f672d4a0bca714da9676cbd049d | O=C(NCc1cccnc1)c1ccc(Nc2nccn3ncnc23)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.C-[O;H0;D2;+0:10]-[c:11](:[c:12]-[C:13](-[#7:14])=[O;D1;H0:15]):[c:16]:[c:17](-[NH2;D1;+0:18]):[c:19]>>[#7:14]-[C:13](=[O;D1;H0:15])-[c:12]:[c:11](-[OH;D1;+0:10]):[c:16]:[c:17](-[NH;D2;+0:18]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5... | null | [] | null | null | null | null | 5,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine (285 mg, 1.03 mmol) and 4-amino-2-methoxy-N-[(6-methylpyridin-3-yl)methyl]benzamide (280 mg, 1.03 mmol) are stirred in iPrOH (5 mL) and HBr (48% aq., 380 μL) is added. The mixture is heated at reflux for 24 hours. The cooled suspension is poured into NaHCO3 (sat. aq., 25 mL) a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Primary amine | Aromatic alcohol.Secondary amine | c1cn2ncnc2cn1 | c1cn2ncnc2cn1 | c1ccncc1.c1ccccc1.c1cn2ncnc2cn1 | HBr | O.CC(C)O | null | null | Brc1ncc(Br)n2ncnc12.COc1cc(N)ccc1C(=O)NCc1ccc(C)nc1>O.CC(C)O>Cc1ccc(CNC(=O)c2ccc(Nc3ncc(Br)n4ncnc34)cc2O)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a4ed936621f141269e1e5d0a8eea41f3 | CO.Cc1ccc(CNC(=O)c2ccc(Nc3ncc(Br)n4ncnc34)cc2O)cn1.OB(O)c1cn[nH]c1>>COc1cc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)ccc1C(=O)NCc1ccc(C)nc1 | S(=O)(=O)(C)O.CO.N1N=CC(=C1)B(O)O.BrC1=CN=C(C=2N1N=CN2)NC2=CC(=C(C(=O)NCC=1C=NC(=CC1)C)C=C2)O.C(=O)([O-])[O-].[K+].[K+]>>COC1=C(C(=O)NCC=2C=NC(=CC2)C)C=CC(=C1)NC=1C=2N(C(=CN1)C=1C=NNC1)N=CN2 | O[CH3:1].Br[c:10]1[cH:9][n:8][c:7]([NH:6][c:5]2[cH:4][c:3]([OH:2])[c:23]([C:24](=[O:25])[NH:26][CH2:27][c:28]3[cH:29][cH:30][c:31]([CH3:32])[n:33][cH:34]3)[cH:22][cH:21]2)[c:20]2[n:16]1[n:17][cH:18][n:19]2.OB(O)[c:11]1[cH:12][n:13][nH:14][cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:... | CO.Cc1ccc(CNC(=O)c2ccc(Nc3ncc(Br)n4ncnc34)cc2O)cn1.OB(O)c1cn[nH]c1 | COc1cc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)ccc1C(=O)NCc1ccc(C)nc1 | null | null | CO.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 8295d8dececbac203070bd99fb61929320bf39ddf2b72d768876bc703cc58d7b | f5eba816ddabe8705e2883ca2473fe0e738ffcc54103fca4c8d83d6d2a00241c | O=C(NCc1cccnc1)c1ccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.[#7:10]-[C:11](=[O;D1;H0:12])-[c:13]:[c:14](-[OH;D1;+0:15]):[c:16].O-B(-O)-[c;H0;D3;+0:17]1:[c:18]:[#7;a:19]:[#7;a:20]:[c:21]:1.O-[CH3;D1;+0:22]>>[#7;a:19]1:[#7;a:20]:[c:21]:[c;H0;D3;+0:17](-[c;H0;D3;+0:1]2:[c:2]:[#7;a:3]:[c:4]:[c:5]3:[... | null | [] | null | null | 30 | SECOND | Pyrazole-4-boronic acid (19 mg, 0.17 mmol), 4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-2-hydroxy-N-[(6-methyl-pyridin-3-yl)methyl]benzamide (40 mg, 0.085 mmol), K2CO3 (24 mg, 0.17 mmol) and Pd(dppf)Cl2CH2Cl2 (4 mg, 0.005 mmol) are weighed into a sealable tube. The tube is flushed with nitrogen and dioxane-wate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol.Boronic acid.Methanol | Ether | c1cn2ncnc2cn1.c1cn[nH]c1 | c1cn[nH]c1.c1cn2ncnc2cn1 | c1ccccc1.c1cn[nH]c1.c1cn2ncnc2cn1.c1ccncc1 | HBr.B | CO.C(Cl)Cl | null | 0.008333 | CO.Cc1ccc(CNC(=O)c2ccc(Nc3ncc(Br)n4ncnc34)cc2O)cn1.OB(O)c1cn[nH]c1>CO.C(Cl)Cl>COc1cc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)ccc1C(=O)NCc1ccc(C)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-873f23cfc9084ae2bf7e9ba4c604e5c3 | COc1cc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)ccc1C(=O)NCc1ccc(C)nc1.NCc1ccccc1>>COc1cc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)ccc1C(=O)NCc1ccccc1 | COC1=C(C(=O)NCC=2C=NC(=CC2)C)C=CC(=C1)NC=1C=2N(C(=CN1)C=1C=NNC1)N=CN2.C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)NC(C1=C(C=C(C=C1)NC=1C=2N(C(=CN1)C=1C=NNC1)N=CN2)OC)=O | Cc1cc[c:28]([CH2:27][NH:26][C:24]([c:23]2[c:3]([O:2][CH3:1])[cH:4][c:5]([NH:6][c:7]3[n:8][cH:9][c:10](-[c:11]4[cH:12][n:13][nH:14][cH:15]4)[n:16]4[n:17][cH:18][n:19][c:20]34)[cH:21][cH:22]2)=[O:25])[cH:33]n1.NCc1c[cH:32][cH:31][cH:30][cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][... | COc1cc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)ccc1C(=O)NCc1ccc(C)nc1.NCc1ccccc1 | COc1cc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)ccc1C(=O)NCc1ccccc1 | null | null | null | Miscellaneous | OtherReaction | d1e52c14e3c13261c493bba43efa0cd5dea570c8557c0c45e5137a6ced83376d | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=C(NCc1ccccc1)c1ccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)cc1 | C-c1:c:c:[c;H0;D3;+0:1](-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5]):[cH;D2;+0:6]:n:1.N-C-c1:[cH;D2;+0:7]:[c:8]:[c:9]:[cH;D2;+0:10]:c:1>>[O;D1;H0:5]=[C:4]-[#7:3]-[C:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:7]:[c:8]:[c:9]:[cH;D2;+0:10]:[cH;D2;+0:6]:1 | null | [] | null | null | null | null | This compound may be prepared using the methods described for Compound 120, using benzylamine in step 1. LCMS: Rt 1.62 min (100%) m/z (ESI) 440 (M+H)+.
Conditions: See reaction.notes.procedure_details.
Workup: This compound may be prepared | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccncc1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1cn[nH]c1.c1cn2ncnc2cn1.c1ccccc1 | Other | null | null | null | COc1cc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)ccc1C(=O)NCc1ccc(C)nc1.NCc1ccccc1>>COc1cc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)ccc1C(=O)NCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5a9e8cf340204f16a39d32d54c680c26 | Brc1ncc(Br)n2ncnc12.CCOC(=O)c1cccc(N)c1>>CCOC(=O)c1cccc(Nc2ncc(Br)n3ncnc23)c1 | BrC1=CN=C(C=2N1N=CN2)Br.NC=1C=C(C(=O)OCC)C=CC1.Br>>C(C)OC(C1=CC(=CC=C1)NC=1C=2N(C(=CN1)Br)N=CN2)=O | Br[c:12]1[n:13][cH:14][c:15]([Br:16])[n:17]2[n:18][cH:19][n:20][c:21]12.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH2:11])[cH:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH:11][c:12]2[n:13][cH:14][c:15]([Br:16])[n:17]3[n:18][cH:19][n:20][c:21]23)[cH:22]1 | Brc1ncc(Br)n2ncnc12.CCOC(=O)c1cccc(N)c1 | CCOC(=O)c1cccc(Nc2ncc(Br)n3ncnc23)c1 | null | null | CC(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | aecfb0ede2c5d7901fea69101287828edf21f7a6e48b6ff83fe43de0688f1ef1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccn3ncnc23)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 98 | [{"value": 98.0, "product": "C(C)OC(C1=CC(=CC=C1)NC=1C=2N(C(=CN1)Br)N=CN2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | 5,8-Dibromo-[1,2,4]triazolo[1,5-a]pyrazine (1.39 g, 5.00 mmol) and ethyl 3-aminobenzoate (0.93 g, 5.60 mmol) are stirred in iPrOH (10 mL) and HBr (48% aq., 1.14 mL, 10 mmol) is added. The mixture is heated at 85° C. for 4 h and then cooled to rt and quenched with NaHCO3 (sat. aq., 25 mL). The resulting suspension is co... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cn2ncnc2cn1 | c1cn2ncnc2cn1 | c1ccccc1.c1cn2ncnc2cn1 | HBr | CC(C)O | 85 | null | Brc1ncc(Br)n2ncnc12.CCOC(=O)c1cccc(N)c1>CC(C)O>CCOC(=O)c1cccc(Nc2ncc(Br)n3ncnc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e25402d3b56c47beafa2a07d55f06a9a | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCOC(=O)c1cccc(Nc2ncc(Br)n3ncnc23)c1>>CCOC(=O)c1cccc(N(C(=O)OC(C)(C)C)c2ncc(Br)n3ncnc23)c1 | C(C)OC(C1=CC(=CC=C1)NC=1C=2N(C(=CN1)Br)N=CN2)=O.O(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>C(C)OC(C1=CC(=CC=C1)N(C(=O)OC(C)(C)C)C=1C=2N(C(=CN1)Br)N=CN2)=O | CC(C)(C)OC(=O)O[C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH:11][c:19]2[n:20][cH:21][c:22]([Br:23])[n:24]3[n:25][cH:26][n:27][c:28]23)[cH:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([N:11]([C:12](=[O:13])[O:14][C:15]([... | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCOC(=O)c1cccc(Nc2ncc(Br)n3ncnc23)c1 | CCOC(=O)c1cccc(N(C(=O)OC(C)(C)C)c2ncc(Br)n3ncnc23)c1 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Protection | Boc amine protection with Boc anhydride | 179c37a0cfe150b9a322c3349c8b39605fd97b04b0abb3f5b3c182be0494cd4b | 7c9d9ba915c29b1020a278f50f3c8f9cc1fd09ebab5bff22f0c1b047d4ae169a | c1ccc(Nc2nccn3ncnc23)cc1 | C-C(-C)(-C)-O-C(=O)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[c:8]:[c:9](-[NH;D2;+0:10]-[c:11]1:[#7;a:12]:[c:13]:[c:14]:[#7;a:15]2:[#7;a:16]:[c:17]:[#7;a:18]:[c:19]:2:1):[c:20]>>[C;D1;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:10](-... | 81.1 | [{"value": 81.1, "product": "C(C)OC(C1=CC(=CC=C1)N(C(=O)OC(C)(C)C)C=1C=2N(C(=CN1)Br)N=CN2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 3-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)benzoic acid ethyl ester (1.79 g, 4.93 mmol) in DCM (20 mL) is stirred under N2 at rt and BOC2O (1.34 g, 6.16 mmol) and DMAP (0.30 g, 2.46 mmol) are added. Stirring is continued for 2 h, when LCMS indicates complete conversion of the starting material. Th... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carbonic Ester.Carbonic Ester.Secondary amine.Boc.Boc | Carbamic ester | null | null | c1ccccc1.c1cn2ncnc2cn1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 2 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCOC(=O)c1cccc(Nc2ncc(Br)n3ncnc23)c1>CN(C)C=1C=CN=CC1.C(Cl)Cl>CCOC(=O)c1cccc(N(C(=O)OC(C)(C)C)c2ncc(Br)n3ncnc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-330b23e505d84149a2cbb0351f283546 | CC1(C)OB(c2cn[nH]c2)OC1(C)C.CCOC(=O)c1cccc(N(C(=O)OC(C)(C)C)c2ncc(Br)n3ncnc23)c1>>CCOC(=O)c1cccc(N(C(=O)OC(C)(C)C)c2ncc(-c3cn[nH]c3)n3ncnc23)c1 | C(C)OC(C1=CC(=CC=C1)N(C(=O)OC(C)(C)C)C=1C=2N(C(=CN1)Br)N=CN2)=O.CC1(OB(OC1(C)C)C=1C=NNC1)C.C(=O)([O-])[O-].[K+].[K+]>>C(C)OC(C1=CC(=CC=C1)N(C=1C=2N(C(=CN1)C=1C=NNC1)N=CN2)C(=O)OC(C)(C)C)=O | CC1(C)OB([c:23]2[cH:24][n:25][nH:26][cH:27]2)OC1(C)C.Br[c:22]1[cH:21][n:20][c:19]([N:11]([c:10]2[cH:9][cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:33]2)[C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[c:32]2[n:28]1[n:29][cH:30][n:31]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([N:... | CC1(C)OB(c2cn[nH]c2)OC1(C)C.CCOC(=O)c1cccc(N(C(=O)OC(C)(C)C)c2ncc(Br)n3ncnc23)c1 | CCOC(=O)c1cccc(N(C(=O)OC(C)(C)C)c2ncc(-c3cn[nH]c3)n3ncnc23)c1 | null | null | O1CCOCC1.O | C-C Coupling | Suzuki coupling with boronic esters | 3b077e58a8068174133a7eecad35957570f9290725408c31a955826b02d2e470 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | c1ccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.C-C1(-C)-O-B(-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[#7;a:13]:[c:14]:2)-O-C-1(-C)-C>>[#7;a:3]1:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[#7;a:13]:[c:14]:2):[c:2]:1 | 108.6 | [{"value": 100.0, "product": "C(C)OC(C1=CC(=CC=C1)N(C=1C=2N(C(=CN1)C=1C=NNC1)N=CN2)C(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 108.6, "product": "C(C)OC(C1=CC(=CC=C1)N(C=1C=2N(C(=CN1)C=1C=NNC1)N=CN2)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 115 | CELSIUS | null | null | Nitrogen is bubbled through a mixture of 3-[(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-tert-butoxycarbonyl-amino]benzoic acid ethyl ester (0.58 g, 1.25 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (0.49 g, 2.50 mmol), K2CO3 (0.35 g, 2.50 mmol) and Pd(dppf)Cl2DCM (102 mg, 0.125 mmol) in dioxane ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1cn[nH]c1.c1cn2ncnc2cn1 | c1cn[nH]c1.c1cn2ncnc2cn1 | c1ccccc1.c1cn[nH]c1.c1cn2ncnc2cn1 | HBr.B | O1CCOCC1.O | 115 | null | CC1(C)OB(c2cn[nH]c2)OC1(C)C.CCOC(=O)c1cccc(N(C(=O)OC(C)(C)C)c2ncc(Br)n3ncnc23)c1>O1CCOCC1.O>CCOC(=O)c1cccc(N(C(=O)OC(C)(C)C)c2ncc(-c3cn[nH]c3)n3ncnc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-828742442cf1402b967da9c94c959a02 | CC(C)(C)OC(=O)N(c1cccc(C(=O)O)c1)c1ncc(-c2cn[nH]c2)n2ncnc12.CCN>>CCNC(=O)c1cccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)c1 | C(C)(C)(C)OC(=O)N(C=1C=C(C(=O)O)C=CC1)C=1C=2N(C(=CN1)C=1C=NNC1)N=CN2.C(C)N.Cl.C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=C5)N=N4.F[P-](F)(F)(F)(F)F>>C(C)NC(C1=CC(=CC=C1)NC=1C=2N(C(=CN1)C=1C=NNC1)N=CN2)=O | CC(C)(C)OC(=O)[N:11]([c:10]1[cH:9][cH:8][cH:7][c:6]([C:4](O)=[O:5])[cH:26]1)[c:12]1[n:13][cH:14][c:15](-[c:16]2[cH:17][n:18][nH:19][cH:20]2)[n:21]2[n:22][cH:23][n:24][c:25]12.[CH3:1][CH2:2][NH2:3]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH:11][c:12]2[n:13][cH:14][c:15](-[c:16]3[cH:17][n:18][nH... | CC(C)(C)OC(=O)N(c1cccc(C(=O)O)c1)c1ncc(-c2cn[nH]c2)n2ncnc12.CCN | CCNC(=O)c1cccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)c1 | null | null | CO.CCO.C(C)N(CC)CC.CN(C)C=O | Acylation | OtherReaction | f10fdabbb25888046326b895dd209630fab45b1d73614d556710fe29012f39e4 | 9f74be20683ae20656a7135e9a9eaad2dfa782f75ac656d32f38d1324fe876ad | c1ccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5](-[C;H0;D3;+0:6](-O)=[O;D1;H0:7]):[c:8])-[c:9]1:[#7;a:10]:[c:11]:[c:12]:[#7;a:13]2:[#7;a:14]:[c:15]:[#7;a:16]:[c:17]:2:1.[C;D1;H3:18]-[C:19]-[NH2;D1;+0:20]>>[C;D1;H3:18]-[C:19]-[NH;D2;+0:20]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:5](:[c:8]):[c:4]:[c:2](-[NH;D2;+0:1]... | 20.1 | [{"value": 20.1, "product": "C(C)NC(C1=CC(=CC=C1)NC=1C=2N(C(=CN1)C=1C=NNC1)N=CN2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 3-{tert-Butoxycarbonyl-[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-amino}benzoic acid (42 mg, 0.10 mmol), ethylamine (12 M aq., 42 μL, 0.50 mmol), and triethylamine (28 μL, 0.20 mmol) are stirred in DMF (0.30 mL) and PyBOP (57 mg, 0.11 mmol) is added. Stirring is continued overnight. The reaction mixture i... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Secondary amide.Secondary amine | null | null | c1ccccc1.c1cn[nH]c1.c1cn2ncnc2cn1 | HO- | CO.CCO.C(C)N(CC)CC.CN(C)C=O | null | 8 | CC(C)(C)OC(=O)N(c1cccc(C(=O)O)c1)c1ncc(-c2cn[nH]c2)n2ncnc12.CCN>CO.CCO.C(C)N(CC)CC.CN(C)C=O>CCNC(=O)c1cccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7c7545711ee54f68bf948b0658f08455 | CCNC(=O)c1cccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)c1.NCc1ccc(O)cc1>>O=C(NCc1ccc(O)cc1)c1cccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)c1 | C(C)NC(C1=CC(=CC=C1)NC=1C=2N(C(=CN1)C=1C=NNC1)N=CN2)=O.OC1=CC=C(CN)C=C1>>OC1=CC=C(CNC(C2=CC(=CC=C2)NC=2C=3N(C(=CN2)C=2C=NNC2)N=CN3)=O)C=C1 | CCN[C:2](=[O:1])[c:12]1[cH:13][cH:14][cH:15][c:16]([NH:17][c:18]2[n:19][cH:20][c:21](-[c:22]3[cH:23][n:24][nH:25][cH:26]3)[n:27]3[n:28][cH:29][n:30][c:31]23)[cH:32]1.[NH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1)[c:12]1[cH:13][cH:14... | CCNC(=O)c1cccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)c1.NCc1ccc(O)cc1 | O=C(NCc1ccc(O)cc1)c1cccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)c1 | null | null | null | Acylation | OtherReaction | 8ccec54884e2cbe7f97f6cea5ae365674b20e64bfde0c57faeea449854021acc | 4accd3f274dad8ca7d44350b7d7da15181b5e5579c068528178b23416d2aea4a | O=C(NCc1ccccc1)c1cccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)c1 | C-C-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]-[c:8])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | This compound may be prepared using methods as described for Compound 129, using 4-hydroxybenzylamine in step 5. LCMS: Rt=0.98 min (100%), m/z (ESI) 427 (M+H)+.
Conditions: See reaction.notes.procedure_details.
Workup: This compound may be prepared | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1cn[nH]c1.c1cn2ncnc2cn1 | Other | null | null | null | CCNC(=O)c1cccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)c1.NCc1ccc(O)cc1>>O=C(NCc1ccc(O)cc1)c1cccc(Nc2ncc(-c3cn[nH]c3)n3ncnc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de4280073ef14b95aee133186ee3a2e6 | NC(=O)c1cc(B(O)O)cs1.O=C(Cc1ccccc1)Nc1ccc(Nc2ncc(Br)n3ncnc23)cn1>>NC(=O)c1cc(-c2cnc(Nc3ccc(NC(=O)Cc4ccccc4)nc3)c3ncnn23)cs1 | COC1=C(C(=O)NCC=2C=NC(=CC2)C)C=CC(=C1)NC=1C=2N(C(=CN1)C=1C=NNC1)N=CN2.BrC1=CN=C(C=2N1N=CN2)NC=2C=CC(=NC2)NC(CC2=CC=CC=C2)=O.NC(=O)C=1SC=C(C1)B(O)O>>C1(=CC=CC=C1)CC(=O)NC1=CC=C(C=N1)NC=1C=2N(C(=CN1)C=1C=C(SC1)C(=O)N)N=CN2 | OB(O)[c:6]1[cH:5][c:4]([C:2]([NH2:1])=[O:3])[s:34][cH:33]1.Br[c:7]1[cH:8][n:9][c:10]([NH:11][c:12]2[cH:13][cH:14][c:15]([NH:16][C:17](=[O:18])[CH2:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[n:26][cH:27]2)[c:28]2[n:29][cH:30][n:31][n:32]12>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]([NH:11][c:12... | NC(=O)c1cc(B(O)O)cs1.O=C(Cc1ccccc1)Nc1ccc(Nc2ncc(Br)n3ncnc23)cn1 | NC(=O)c1cc(-c2cnc(Nc3ccc(NC(=O)Cc4ccccc4)nc3)c3ncnn23)cs1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 43d3551703d0592fc09d7e8a4fc6f079755043a628c77b3213d51db104641e47 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(Cc1ccccc1)Nc1ccc(Nc2ncc(-c3ccsc3)n3ncnc23)cn1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[#7;a:9]:2:1.O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#16;a:12]:[c:13](-[C:14](-[N;D1;H2:15])=[O;D1;H0:16]):[c:17]:1>>[N;D1;H2:15]-[C:14](=[O;D1;H0:16])-[c:13]1:[#16;a:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[#7;a:3]:[c:4]:[c:5]3:[#7;a:6]:[c:7]:[#... | null | [] | null | null | null | null | This compound may be prepared using methods as described for Compound 120, step 4, using N-[5-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-pyridin-2-yl]-2-phenylacetamide and 2-(aminocarbonyl)thiophene-4-boronic acid. LCMS: Rt 1.06 min (100%) m/z (ESI) 471 (M+H)+.
Conditions: See reaction.notes.procedure_details.
... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccsc1.c1cn2ncnc2cn1 | c1ccsc1.c1cn2ncnc2cn1 | c1ccsc1.c1ccncc1.c1ccccc1.c1cn2ncnc2cn1 | HBr.B | null | null | null | NC(=O)c1cc(B(O)O)cs1.O=C(Cc1ccccc1)Nc1ccc(Nc2ncc(Br)n3ncnc23)cn1>>NC(=O)c1cc(-c2cnc(Nc3ccc(NC(=O)Cc4ccccc4)nc3)c3ncnn23)cs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-412c6895c66746fb9d5be9457be48763 | CC(C)N1CCC(c2ccc(Nc3ncc(-c4cn[nH]c4)n4ncnc34)cc2)CC1.NC(=O)CBr>>NC(=O)CN1CCC(c2ccc(Nc3ncc(-c4cn[nH]c4)n4ncnc34)cc2)CC1 | C(C)(C)N1CCC(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=NNC1)N=CN2.BrCC(=O)N>>N1N=CC(=C1)C1=CN=C(C=2N1N=CN2)NC2=CC=C(C=C2)C2CCN(CC2)CC(=O)N | CC(C)[N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12]([NH:13][c:14]3[n:15][cH:16][c:17](-[c:18]4[cH:19][n:20][nH:21][cH:22]4)[n:23]4[n:24][cH:25][n:26][c:27]34)[cH:28][cH:29]2)[CH2:30][CH2:31]1.Br[CH2:4][C:2]([NH2:1])=[O:3]>>[NH2:1][C:2](=[O:3])[CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[cH:10][cH:11][c:12]([NH:13][c... | CC(C)N1CCC(c2ccc(Nc3ncc(-c4cn[nH]c4)n4ncnc34)cc2)CC1.NC(=O)CBr | NC(=O)CN1CCC(c2ccc(Nc3ncc(-c4cn[nH]c4)n4ncnc34)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 15cc3a5a9d32314b79094a0e5ab12888144a1ec35cfb2d8d6a128315fd0f10a2 | b6177f1fc9b2dcf6edc7b8787c5dfef88aa31b4557820e58fa8b5889998b8498 | c1nc2c(Nc3ccc(C4CCNCC4)cc3)ncc(-c3cn[nH]c3)n2n1 | Br-[CH2;D2;+0:1]-[C:2](-[N;D1;H2:3])=[O;D1;H0:4].C-C(-C)-[N;H0;D3;+0:5](-[C:6]-[C:7])-[C:8]-[C:9]>>[C:7]-[C:6]-[N;H0;D3;+0:5](-[CH2;D2;+0:1]-[C:2](-[N;D1;H2:3])=[O;D1;H0:4])-[C:8]-[C:9] | null | [] | null | null | null | null | This compound may be prepared using methods as described for Compound 84, using 2-bromoacetamide in step 1. LCMS: Rt=0.81 min (100%), m/z (ESI) 418 (M+H)+.
Conditions: See reaction.notes.procedure_details.
Workup: This compound may be prepared | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | Tertiary amine | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1cn[nH]c1.c1cn2ncnc2cn1 | HBr | null | null | null | CC(C)N1CCC(c2ccc(Nc3ncc(-c4cn[nH]c4)n4ncnc34)cc2)CC1.NC(=O)CBr>>NC(=O)CN1CCC(c2ccc(Nc3ncc(-c4cn[nH]c4)n4ncnc34)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e3efd46fcb63474ea53f3e896a9dbfb8 | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2C(F)(F)F)CC1.c1nc2c(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)ncc(-c3cn[nH]c3)n2n1>>CC(C)N1CCN(c2ccc(Nc3ncc(-c4cn[nH]c4)n4ncnc34)cc2C(F)(F)F)CC1 | C1(CC1)CN1CCN(CC1)C1=CC=C(C=C1)NC=1C=2N(C(=CN1)C=1C=NNC1)N=CN2.BrC1=CN=C(C=2N1N=CN2)NC2=CC(=C(C=C2)N2CCN(CC2)C(C)C)C(F)(F)F>>C(C)(C)N1CCN(CC1)C1=C(C=C(C=C1)NC=1C=2N(C(=CN1)C=1C=NNC1)N=CN2)C(F)(F)F | Brc1cnc(N[c:11]2[cH:10][cH:9][c:8]([N:7]3[CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH2:34][CH2:33]3)[c:28]([C:29]([F:30])([F:31])[F:32])[cH:27]2)c2ncnn12.c1cc([NH:12][c:13]2[n:14][cH:15][c:16](-[c:17]3[cH:18][n:19][nH:20][cH:21]3)[n:22]3[n:23][cH:24][n:25][c:26]23)ccc1N1CCN(CC2CC2)CC1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH... | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2C(F)(F)F)CC1.c1nc2c(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)ncc(-c3cn[nH]c3)n2n1 | CC(C)N1CCN(c2ccc(Nc3ncc(-c4cn[nH]c4)n4ncnc34)cc2C(F)(F)F)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 5ddda3b84343a55f86a0261fb38b43781f64e63aa92481f1cf27df1481179a38 | 7d31f47e5761ed6e1805ce0becec02c3b3cb1ec75262e81cbdbb96933cfa3652 | c1nc2c(Nc3ccc(N4CCNCC4)cc3)ncc(-c3cn[nH]c3)n2n1 | Br-c1:c:n:c(-N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):c2:n:c:n:n:1:2.C1-C-C-1-C-N1-C-C-N(-c2:c:c:c(-[NH;D2;+0:6]-[c:7]3:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]4:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:4:3):c:c:2)-C-C-1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#7;a:11]2:[#7;a:12]:[c:13]:[#7;a:14]:[c:... | null | [] | null | null | null | null | This compound may be prepared using methods as described for Compound 46, using (5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-[4-(4-isopropylpiperazin-1-yl)-3-trifluoromethylphenyl]amine. LCMS: Rt=0.99 (95%), m/z (ESI) 472 (M+H)+.
Conditions: See reaction.notes.procedure_details.
Workup: This compound may be prepared | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine.Secondary amine.Tertiary amine.Tertiary amine | Secondary amine | c1ccccc1.c1cn2ncnc2cn1.c1ccccc1.C1CNCCN1.C1CC1 | c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.c1cn[nH]c1.c1cn2ncnc2cn1 | HBr | null | null | null | CC(C)N1CCN(c2ccc(Nc3ncc(Br)n4ncnc34)cc2C(F)(F)F)CC1.c1nc2c(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)ncc(-c3cn[nH]c3)n2n1>>CC(C)N1CCN(c2ccc(Nc3ncc(-c4cn[nH]c4)n4ncnc34)cc2C(F)(F)F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d6cc889528434fa396a38aa8ba73abe0 | CC(C)O.O=C1c2ccccc2C(=O)C1(O)O.[NH4+]>>OC[C@H]1CNC[C@@H](O)[C@@H]1O | C(C)(C)O.O.[NH4+].[OH-].C1=CC=C2C(=C1)C(=O)C(C2=O)(O)O>>C1[C@@H]([C@H]([C@@H](CN1)O)O)CO | C[CH:2]([OH:1])[CH3:6].O=C1c2ccc[cH:4][c:3]2[C:9](=[O:10])[C:7]1(O)[OH:8].[NH4+:5]>>[OH:1][CH2:2][C@H:3]1[CH2:4][NH:5][CH2:6][C@@H:7]([OH:8])[C@@H:9]1[OH:10] | CC(C)O.O=C1c2ccccc2C(=O)C1(O)O.[NH4+] | OC[C@H]1CNC[C@@H](O)[C@@H]1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e73a4ecfdecb42a1d125106a488e57a4c13823fbf77aa549c85a69c894ce7237 | 6501933472fecd70b0b1194b8ef7ca3a85539167470ffd6be89ccc9ea97365d3 | C1CCNCC1 | C-[CH;D3;+0:1](-[CH3;D1;+0:2])-[O;D1;H1:3].O-[C;H0;D4;+0:4]1(-[O;D1;H1:5])-C(=O)-c2:c:c:c:[cH;D2;+0:6]:[c;H0;D3;+0:7]:2-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9].[NH4+;D0:10]>>[O;D1;H1:3]-[CH2;D2;+0:1]-[C@H;D3;+0:7]1-[CH2;D2;+0:6]-[NH;D2;+0:10]-[CH2;D2;+0:2]-[C@@H;D3;+0:4](-[O;D1;H1:5])-[C@@H;D3;+0:8]-1-[OH;D1;+0:9] | null | [] | null | null | 72 | HOUR | TLC was performed on the different fractions (silica gel, isopropanol:water:NH4OH (7:2:1) and detection was via imino sugar and ninhydrin spray. Fractions testing positive with the imino-sugar sprays were analyzed to determine purity, then combined and lyophilized for 72 hours.
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Secondary alcohol.Tertiary alcohol.Tertiary alcohol | Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary amine | c1ccc2c(c1)CCC2 | C1CCNCC1 | C1CCNCC1 | HO- | null | null | 72 | CC(C)O.O=C1c2ccccc2C(=O)C1(O)O.[NH4+]>>OC[C@H]1CNC[C@@H](O)[C@@H]1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-072ab9e7dac74a0bbec4b4073a868935 | OC[C@H]1CNC[C@@H](O)[C@@H]1O>>OC[C@H]1CNC[C@@H](O)[C@@H]1O | C1[C@@H]([C@H]([C@@H](CN1)O)O)CO.Cl>>C1[C@@H]([C@H]([C@@H](CN1)O)O)CO.Cl | [OH:2][CH2:3][C@H:4]1[CH2:5][NH:6][CH2:7][C@@H:8]([OH:9])[C@@H:10]1[OH:11]>>[OH:2][CH2:3][C@H:4]1[CH2:5][NH:6][CH2:7][C@@H:8]([OH:9])[C@@H:10]1[OH:11] | OC[C@H]1CNC[C@@H](O)[C@@H]1O | OC[C@H]1CNC[C@@H](O)[C@@H]1O | null | null | CO.CC(=O)C.C(C)(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C1CCNCC1 | null | null | [] | null | null | 8 | HOUR | Isofagomine free base (30 mg) was dissolved in MeOH (5 mL) and 4 N HCl (0.5 mL) in isopropanol and acetone (4.0 mL). The sample was stored refrigerated overnight and filtered. Crystals were observed in the solution. However, when filtered, the product was a yellow substance having a glue-like consistency.
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CCNCC1 | null | CO.CC(=O)C.C(C)(C)O | null | 8 | OC[C@H]1CNC[C@@H](O)[C@@H]1O>CO.CC(=O)C.C(C)(C)O>OC[C@H]1CNC[C@@H](O)[C@@H]1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-30f01609220f49bf9ce6795f15a73cfa | O=C[C@@H](O)[C@H](O)[C@H](O)CO.OCc1ccccc1>>O=C[C@](O)(Cc1ccccc1)[C@H](O)[C@H](O)CO | O=C[C@@H](O)[C@H](O)[C@H](O)CO.C(C1=CC=CC=C1)O.C(C)(=O)Cl>>C(C1=CC=CC=C1)[C@](C=O)(O)[C@H](O)[C@H](O)CO | [O:1]=[CH:2][C@@H:3]([OH:4])[C@H:12]([OH:13])[C@H:14]([OH:15])[CH2:16][OH:17].O[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[O:1]=[CH:2][C@:3]([OH:4])([CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[C@H:12]([OH:13])[C@H:14]([OH:15])[CH2:16][OH:17] | O=C[C@@H](O)[C@H](O)[C@H](O)CO.OCc1ccccc1 | O=C[C@](O)(Cc1ccccc1)[C@H](O)[C@H](O)CO | null | null | CC(C)(C)OC | C-C Coupling | OtherReaction | f42956668c59a62a2fe14af6f60169215fa9f76b367e8cc8580fced345e044dd | ad507317811a44d17061f0a40d99a489d6f22dc298e6a9d74de85776c8c90e8d | c1ccccc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[O;D1;H1:7])-[C@H;D3;+0:8](-[O;D1;H1:9])-[C:10]=[O;D1;H0:11]>>[C:5]-[C:6](-[O;D1;H1:7])-[C@;H0;D4;+0:8](-[O;D1;H1:9])(-[C:10]=[O;D1;H0:11])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 35 | CELSIUS | 8 | HOUR | D-Arabinose (50 kg, 330.04 moles) and benzyl alcohol (132.2 kg, 4.33 equivalents) were stirred and heated to 35° C. Acetyl chloride (10.9 kg, 0.42 equivalents), keeping the temperature <45° C., then stirred 50° C. overnight. The mixture was cooled to 20° C. and diluted with MTBE (600 kg). The mixture was stirred for 0.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol | Aldehyde.Tertiary alcohol | null | null | c1ccccc1 | HO- | CC(C)(C)OC | 35 | 8 | O=C[C@@H](O)[C@H](O)[C@H](O)CO.OCc1ccccc1>CC(C)(C)OC>O=C[C@](O)(Cc1ccccc1)[C@H](O)[C@H](O)CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-514b8a8d2cd3433a8ba8ddfb06d0d84a | O=C(O)[C@H](O)[C@@H](O)C(=O)O>>O=C([O-])[C@H](O)[C@@H](O)C(=O)[O-] | C([C@H](O)[C@@H](O)C(=O)O)(=O)O.C1[C@@H]([C@H]([C@@H](CN1)O)O)CO>>C1[C@@H]([C@H]([C@@H](CN1)O)O)CO.C(=O)([O-])[C@H](O)[C@@H](O)C(=O)[O-] | [O:1]=[C:2]([OH:3])[C@H:4]([OH:5])[C@@H:6]([OH:7])[C:8](=[O:9])[OH:10]>>[O:1]=[C:2]([O-:3])[C@H:4]([OH:5])[C@@H:6]([OH:7])[C:8](=[O:9])[O-:10] | O=C(O)[C@H](O)[C@@H](O)C(=O)O | O=C([O-])[C@H](O)[C@@H](O)C(=O)[O-] | null | null | O | Oxidation | OtherReaction | 4af04878ecd22d61c6d7d46db52e672904d5e72408231940a5cea872324a16a2 | 4e878a1fdc9370141a3ed00507bdfaa037f36d163bb15c5076375a9835c80b8f | null | [O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[O-;H0;D1:8]-[C:6](=[O;D1;H0:7])-[C:5]-[C:4]-[C:2](-[O-;H0;D1:3])=[O;D1;H0:1] | 137.5 | [{"value": 91.0, "product": "C1[C@@H]([C@H]([C@@H](CN1)O)O)CO.C(=O)([O-])[C@H](O)[C@@H](O)C(=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 137.5, "product": "C1[C@@H]([C@H]([C@@H](CN1)O)O)CO.C(=O)([O-])[C@H](O)[C@@H](O)C(=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of L-(+)-tartaric acid (102 mg, 0.679 mmol) in deionized water (1.0 mL) was added into the solution of isofagomine (200 mg, 2.0 equivalents) dissolved in deionized water (2.0 mL) at room temperature. The solution was stirred for 10 min and lyophilized overnight. The residue was further dried under vacuum at ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | null | null | null | null | null | O | null | 0.166667 | O=C(O)[C@H](O)[C@@H](O)C(=O)O>O>O=C([O-])[C@H](O)[C@@H](O)C(=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-67b86b27891f4c62aced766825510af3 | O=C(O)[C@@H](O)[C@H](O)C(=O)O>>O=C([O-])[C@@H](O)[C@H](O)C(=O)[O-] | C([C@@H](O)[C@H](O)C(=O)O)(=O)O.C1[C@@H]([C@H]([C@@H](CN1)O)O)CO>>C1[C@@H]([C@H]([C@@H](CN1)O)O)CO.C(=O)([O-])[C@@H](O)[C@H](O)C(=O)[O-] | [O:1]=[C:2]([OH:3])[C@@H:4]([OH:5])[C@H:6]([OH:7])[C:8](=[O:9])[OH:10]>>[O:1]=[C:2]([O-:3])[C@@H:4]([OH:5])[C@H:6]([OH:7])[C:8](=[O:9])[O-:10] | O=C(O)[C@@H](O)[C@H](O)C(=O)O | O=C([O-])[C@@H](O)[C@H](O)C(=O)[O-] | null | null | O | Oxidation | OtherReaction | 4af04878ecd22d61c6d7d46db52e672904d5e72408231940a5cea872324a16a2 | 4e878a1fdc9370141a3ed00507bdfaa037f36d163bb15c5076375a9835c80b8f | null | [O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[C:4]-[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[O-;H0;D1:8]-[C:6](=[O;D1;H0:7])-[C:5]-[C:4]-[C:2](-[O-;H0;D1:3])=[O;D1;H0:1] | 143.3 | [{"value": 95.0, "product": "C1[C@@H]([C@H]([C@@H](CN1)O)O)CO.C(=O)([O-])[C@@H](O)[C@H](O)C(=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 143.3, "product": "C1[C@@H]([C@H]([C@@H](CN1)O)O)CO.C(=O)([O-])[C@@H](O)[C@H](O)C(=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of D-(-)-tartaric acid (102 mg, 0.679 mmol) in deionized water (1.0 mL) was added into the solution of isofagomine (200 mg, 2.0 equivalents) dissolved in deionized water (2.0 mL) at room temperature. The solution was stirred for 10 min and lyophilized overnight. The residue was further dried under vacuum at ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | null | null | null | null | null | O | null | 0.166667 | O=C(O)[C@@H](O)[C@H](O)C(=O)O>O>O=C([O-])[C@@H](O)[C@H](O)C(=O)[O-] |
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