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-09d853b9f24644af997a1a56318ef3e7 | CCOC(=O)CC(=O)[O-].O=C(O)c1cccnc1>>CCOC(=O)CC(=O)c1cccnc1 | [Mg+2].[Cl-].[Cl-].[K+].C(CC(=O)[O-])(=O)OCC.C(C1=CN=CC=C1)(=O)O.C(=O)(C=1NC=CN1)C=1NC=CN1.[N-]1C=NC=C1>>O=C(CC(=O)OCC)C=1C=NC=CC1 | O=C([O-])[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].O[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][n:13][cH:14]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][n:13][cH:14]1 | CCOC(=O)CC(=O)[O-].O=C(O)c1cccnc1 | CCOC(=O)CC(=O)c1cccnc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 6e144dbbf281048ca902de5a0a54b731c99776ef982e7e4aab4fdee308ea4d06 | d5654c9a84fc42e383a200090b60ea1c499fce894824745135207b080d8463d3 | c1ccncc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].O=C(-[O-])-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]>>[C:12]-[#8:11]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 49.6 | [{"value": 49.5, "product": "O=C(CC(=O)OCC)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.6, "product": "O=C(CC(=O)OCC)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of nicotinic acid 5.00 g (40.6 mmol) in tetrahydrofuran 50 mL was added carbonyl diimidazole 9.76 g (60.9 mmol) at 5° C. and stirred at room temperature for 1 hour. In a separate flask, a suspension of MgCl2 4.64 g (48.7 mmol) and ethyl malonate potassium salt 10.37 g (60.92 mmol) in tetrahydrofuran 50 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ketone | null | null | c1ccncc1 | HO- | O1CCCC1 | null | 1 | CCOC(=O)CC(=O)[O-].O=C(O)c1cccnc1>O1CCCC1>CCOC(=O)CC(=O)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac8e82d8f35c4f6c97fbccb624da542a | CCC(Cl)C(=O)OC.COc1c(O)ccc2c1N=C(C=C(O)c1cccnc1)N1CCN=C21>>COC(=O)CCCOc1ccc2c(c1OC)N=C(C=C(O)c1cccnc1)N1CCN=C21 | O.Cl.OC(=CC1=NC=2C(=C(C=CC2C=2N1CCN2)O)OC)C=2C=NC=CC2.ClC(C(=O)OC)CC.C([O-])([O-])=O.[K+].[K+]>>OC(=CC1=NC=2C(=C(C=CC2C=2N1CCN2)OCCCC(=O)OC)OC)C=2C=NC=CC2 | Cl[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH3:7].[OH:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([c:14]1[O:15][CH3:16])[N:17]=[C:18]([CH:19]=[C:20]([OH:21])[c:22]1[cH:23][cH:24][cH:25][n:26][cH:27]1)[N:28]1[CH2:29][CH2:30][N:31]=[C:32]21>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]2[c:13]([c:... | CCC(Cl)C(=O)OC.COc1c(O)ccc2c1N=C(C=C(O)c1cccnc1)N1CCN=C21 | COC(=O)CCCOc1ccc2c(c1OC)N=C(C=C(O)c1cccnc1)N1CCN=C21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | a60236748d2543bdb97e5465447a595cd9bb5fef4e3fe96ed6af652af51cd157 | 94a54f0a6e629a85ca32b8fd3cf243ab64283e31ecfe8705ffe0df2304c488b4 | C(=Cc1cccnc1)C1=Nc2ccccc2C2=NCCN12 | Cl-[CH;D3;+0:1](-[C:2]-[CH3;D1;+0:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 59.3 | [{"value": 59.3, "product": "OC(=CC1=NC=2C(=C(C=CC2C=2N1CCN2)OCCCC(=O)OC)OC)C=2C=NC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.3, "product": "OC(=CC1=NC=2C(=C(C=CC2C=2N1CCN2)OCCCC(=O)OC)OC)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 4 | HOUR | A mixture of 5-(2-hydroxy-2-pyridin-3-ylvinyl)-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-8-ol hydrochloride (Example 1-4) 50.4 mg (0.14 mmol), methyl chloro-butyrate 22.2 mg (0.16 mmmol) and potassium carbonate 186.9 mg (1.35 mmmol) in N,N-dimethylformamide 1 mL was stirred at 120° C. for 4 hours. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccncc1.C1=Nc2ccccc2C2=NCCN12 | HCl | CN(C=O)C | 120 | 4 | CCC(Cl)C(=O)OC.COc1c(O)ccc2c1N=C(C=C(O)c1cccnc1)N1CCN=C21>CN(C=O)C>COC(=O)CCCOc1ccc2c(c1OC)N=C(C=C(O)c1cccnc1)N1CCN=C21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3045b9efc34946ce85d6b01e20d51553 | COC(=O)CCCOc1ccc2c(c1OC)N=C(C=C(O)c1cccnc1)N1CCN=C21>>COc1c(OCCCC(=O)O)ccc2c1N=C(C=C(O)c1cccnc1)N1CCN=C21 | OC(=CC1=NC=2C(=C(C=CC2C=2N1CCN2)OCCCC(=O)OC)OC)C=2C=NC=CC2.Cl>>OC(=CC1=NC=2C(=C(C=CC2C=2N1CCN2)OCCCC(=O)O)OC)C=2C=NC=CC2 | C[O:11][C:9]([CH2:8][CH2:7][CH2:6][O:5][c:4]1[c:3]([O:2][CH3:1])[c:15]2[c:14]([cH:13][cH:12]1)[C:31]1=[N:30][CH2:29][CH2:28][N:27]1[C:17]([CH:18]=[C:19]([OH:20])[c:21]1[cH:22][cH:23][cH:24][n:25][cH:26]1)=[N:16]2)=[O:10]>>[CH3:1][O:2][c:3]1[c:4]([O:5][CH2:6][CH2:7][CH2:8][C:9](=[O:10])[OH:11])[cH:12][cH:13][c:14]2[c:15... | COC(=O)CCCOc1ccc2c(c1OC)N=C(C=C(O)c1cccnc1)N1CCN=C21 | COc1c(OCCCC(=O)O)ccc2c1N=C(C=C(O)c1cccnc1)N1CCN=C21 | null | null | [Li+].[OH-].C(C)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C(=Cc1cccnc1)C1=Nc2ccccc2C2=NCCN12 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 51.7 | [{"value": 51.7, "product": "OC(=CC1=NC=2C(=C(C=CC2C=2N1CCN2)OCCCC(=O)O)OC)C=2C=NC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.3, "product": "OC(=CC1=NC=2C(=C(C=CC2C=2N1CCN2)OCCCC(=O)O)OC)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of methyl 4-{[5-(2-hydroxy-2-pyridin-3-ylvinyl)-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-8-yl]oxy}butanoate (example 1-5) 20.0 mg (0.05 mmol) in 1N LiOH solution 0.1 mL and ethanol 1.0 mL was stirred at room temperature for overnight. The reaction mixture was neutralized with 1N HCl solution and concent... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.C1=Nc2ccccc2C2=NCCN12 | Other | [Li+].[OH-].C(C)O | null | null | COC(=O)CCCOc1ccc2c(c1OC)N=C(C=C(O)c1cccnc1)N1CCN=C21>[Li+].[OH-].C(C)O>COc1c(OCCCC(=O)O)ccc2c1N=C(C=C(O)c1cccnc1)N1CCN=C21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c7c40b8ba8c245a6a51c6c57d6b6b973 | Cl>>Cl | OC(=CC1=NC=2C(=C(C=CC2C=2N1CCN2)OCCCC(=O)O)OC)C=2C=NC=CC2.Cl>>Cl.OC(=CC1=NC=2C(=C(C=CC2C=2N1CCN2)OCCCC(=O)O)OC)C=2C=NC=CC2 | [ClH:32]>>[ClH:32] | Cl | Cl | null | null | O1CCOCC1.C(C)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 92 | [{"value": 92.0, "product": "Cl.OC(=CC1=NC=2C(=C(C=CC2C=2N1CCN2)OCCCC(=O)O)OC)C=2C=NC=CC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 4-{[5-(2-hydroxy-2-pyridin-3-ylvinyl)-7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-8-yl]oxy}butanoic acid (Example 1-6) 4.0 mg (9.5 micromol) in 4N HCl in 1,4-dioxane 2.0 mL was stirred at room temperature for 2 hours. The reaction mixture was diluted with diethyl ether. The precipitate was collected to g... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O1CCOCC1.C(C)OCC | null | 2 | Cl>O1CCOCC1.C(C)OCC>Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4bbac139a9334ce9bc2e18c324b691ec | N#Cc1ccccc1N.NCCN>>Nc1ccccc1C1=NCCN1 | NC1=C(C#N)C=CC=C1.C(CN)N>>N1C(=NCC1)C1=C(N)C=CC=C1 | [NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8]#[N:9].N[CH2:10][CH2:11][NH2:12]>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8]1=[N:9][CH2:10][CH2:11][NH:12]1 | N#Cc1ccccc1N.NCCN | Nc1ccccc1C1=NCCN1 | null | P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3 | O | Heteroatom Alkylation and Arylation | OtherReaction | 44acbf70f9cc2ac0a229971bc6e7c77034e28fcd162de6449941e21cd576fef7 | e5ee524a9b0e5a2fe21766a24b1795b0d2b08a43f7dda8289a0ee59c7b4777e1 | c1ccc(C2=NCCN2)cc1 | N-[CH2;D2;+0:1]-[C:2]-[NH2;D1;+0:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[C;H0;D3;+0:5]1=[N;H0;D2;+0:4]-[CH2;D2;+0:1]-[C:2]-[NH;D2;+0:3]-1):[c:8] | 81.4 | [{"value": 81.0, "product": "N1C(=NCC1)C1=C(N)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.4, "product": "N1C(=NCC1)C1=C(N)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 2-Aminobenzonitrile (9.00 g, 76.2 mmol) was added at 0° C. to ethylenediamine (25.5 ml, 381 mmol) in small portions with stirring. After phosphorus pentasulfide (200 mg, 0.900 mmol) was added, the mixture was stirred at 100° C. overnight. After cooling to 0° C., the reaction was diluted with water. The resulting white ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Primary amine | Secondary amine | null | C1=NCCN1 | c1ccccc1.C1=NCCN1 | Other | P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3.O | 0 | null | N#Cc1ccccc1N.NCCN>P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3.O>Nc1ccccc1C1=NCCN1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-98b2241b8f4840818d172daa293a975c | N#CBr.Nc1ccccc1C1=NCCN1>>Br.NC1=Nc2ccccc2C2=NCCN12 | N1C(=NCC1)C1=C(N)C=CC=C1.N#CBr>>Br.N=1CCN2C(=NC=3C=CC=CC3C21)N | [Br:1][C:3]#[N:2].[NH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11]1=[N:12][CH2:13][CH2:14][NH:15]1>>[BrH:1].[NH2:2][C:3]1=[N:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[C:11]2=[N:12][CH2:13][CH2:14][N:15]12 | N#CBr.Nc1ccccc1C1=NCCN1 | Br.NC1=Nc2ccccc2C2=NCCN12 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 4efb46b182c6a436385a7238277900d32b3e1532cf788ff4f8cd430833519b7c | b57bdbe728a8b92000f0fde9e9afe3b122c54cb15f189300cc8bbbea277457ba | C1=Nc2ccccc2C2=NCCN12 | [Br;H0;D1;+0:1]-[C;H0;D2;+0:2]#[N;H0;D1;+0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]-[C:8]1=[#7:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[BrH;D0;+0:1].[NH2;D1;+0:3]-[C;H0;D3;+0:2]1=[N;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]-[C:8]2=[#7:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-2-1 | 60 | [{"value": 60.0, "product": "Br.N=1CCN2C(=NC=3C=CC=CC3C21)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.7, "product": "Br.N=1CCN2C(=NC=3C=CC=CC3C21)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a suspension of 2-(4,5-dihydro-1H-imidazol-2-yl)aniline (5.00 g, 31.0 mmol) in 85% methanol (60 ml) at 0° C. was added cyanogen bromide (3.61 g, 34.1 mmol) by portions. This mixture was stirred at room temperature overnight. After the mixture was concentrated under reduced pressure, the resulting precipitate was col... | 10.6084/m9.figshare.5104873.v1 | null | Haloalkyne.Nitrile.Primary amine.Secondary amine | Primary amine.Tertiary amine | C1=NCCN1 | C1=Nc2ccccc2C2=NCCN12 | C1=Nc2ccccc2C2=NCCN12 | null | CO | null | 8 | N#CBr.Nc1ccccc1C1=NCCN1>CO>Br.NC1=Nc2ccccc2C2=NCCN12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe28142336824e7f9659283a46f912fb | NC1=Nc2ccccc2C2=NCCN12.O=C(O)c1cccnc1>>O=C(NC1=Nc2ccccc2C2=NCCN12)c1cccnc1 | C(C)(C)N(C(C)C)CC.Br.N=1CCN2C(=NC=3C=CC=CC3C21)N.C(C1=CN=CC=C1)(=O)O.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N2CCCC2)(N2CCCC2)N2CCCC2>>N=1CCN2C(=NC=3C=CC=CC3C21)NC(C2=CN=CC=C2)=O | [NH2:3][C:4]1=[N:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[C:12]2=[N:13][CH2:14][CH2:15][N:16]12.O[C:2](=[O:1])[c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]1>>[O:1]=[C:2]([NH:3][C:4]1=[N:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[C:12]2=[N:13][CH2:14][CH2:15][N:16]12)[c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]1 | NC1=Nc2ccccc2C2=NCCN12.O=C(O)c1cccnc1 | O=C(NC1=Nc2ccccc2C2=NCCN12)c1cccnc1 | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC1=Nc2ccccc2C2=NCCN12)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[#7:8]=[C:9]-[#7:10](-[C:11])-[C:12](-[NH2;D1;+0:13])=[#7:14]-[c:15]>>[#7:8]=[C:9]-[#7:10](-[C:11])-[C:12](-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7])=[#7:14]-[c:15] | 83 | [{"value": 83.0, "product": "N=1CCN2C(=NC=3C=CC=CC3C21)NC(C2=CN=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.6, "product": "N=1CCN2C(=NC=3C=CC=CC3C21)NC(C2=CN=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a suspension of 2,3-dihydroimidazo[1,2-c]quinazolin-5-ylamine hydrobromide (500 mg, 1.87 mmol) and nicotinic acid (346 mg, 2.81 mmol) in N,N-dimethyl-formamide (25 ml) at room temperature was added benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (1.46 g, 2.81 mmol) followed by N,N-diisopropyl... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1=Nc2ccccc2C2=NCCN12.c1ccncc1 | HO- | CN(C=O)C | 80 | null | NC1=Nc2ccccc2C2=NCCN12.O=C(O)c1cccnc1>CN(C=O)C>O=C(NC1=Nc2ccccc2C2=NCCN12)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-77f063ab8c0444548594323e71e0a5fc | O=C(NC1=Nc2ccccc2C2=NCCN12)c1cccnc1>>O=C(NC1=Nc2ccccc2C2=NCCN12)c1cccnc1 | N=1CCN2C(=NC=3C=CC=CC3C21)NC(C2=CN=CC=C2)=O.Cl.O1CCOCC1>>Cl.N=1CCN2C(=NC=3C=CC=CC3C21)NC(C2=CN=CC=C2)=O | [O:2]=[C:3]([NH:4][C:5]1=[N:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]2=[N:14][CH2:15][CH2:16][N:17]12)[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1>>[O:2]=[C:3]([NH:4][C:5]1=[N:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]2=[N:14][CH2:15][CH2:16][N:17]12)[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1 | O=C(NC1=Nc2ccccc2C2=NCCN12)c1cccnc1 | O=C(NC1=Nc2ccccc2C2=NCCN12)c1cccnc1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(NC1=Nc2ccccc2C2=NCCN12)c1cccnc1 | null | null | [] | null | null | 1 | HOUR | To a suspension of N-(2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)nicotinamide (150 mg, 0.515 mmol) in tetrahydrofuran (4 ml) at 0° C. was added a 4N solution of hydrochloric acid in 1,4-dioxane (2 ml, 8 mmol). The mixture was stirred at room temperature for 1 h, and concentrated under reduced pressure. The resulting resi... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1=Nc2ccccc2C2=NCCN12.c1ccncc1 | null | O1CCCC1 | null | 1 | O=C(NC1=Nc2ccccc2C2=NCCN12)c1cccnc1>O1CCCC1>O=C(NC1=Nc2ccccc2C2=NCCN12)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0bf9b1a73b7943bf98bae5cd068b69a5 | C1COCCN1.N#Cc1ccc([N+](=O)[O-])cc1[N+](=O)[O-]>>N#Cc1ccc(N2CCOCC2)cc1[N+](=O)[O-] | [N+](=O)([O-])C1=C(C#N)C=CC(=C1)[N+](=O)[O-].N1CCOCC1.O>>N1(CCOCC1)C1=CC(=C(C#N)C=C1)[N+](=O)[O-] | N1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1.O=[N+:7]([O-])[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[c:14]([N+:15](=[O:16])[O-:17])[cH:13]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][c:14]1[N+:15](=[O:16])[O-:17] | C1COCCN1.N#Cc1ccc([N+](=O)[O-])cc1[N+](=O)[O-] | N#Cc1ccc(N2CCOCC2)cc1[N+](=O)[O-] | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | bc0dea069040db48802039025c14b9634c6344e4ef634236a0914ce32ee35aa4 | 7ead7227b7a45c6aa98f47083d1d36f2fd7b34b895239cc9a4160e9dc6908535 | c1ccc(N2CCOCC2)cc1 | N1-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-1.O=[N+;H0;D3:6](-[O-])-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[N;H0;D3;+0:6]1-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-1):[c:9] | 82.8 | [{"value": 74.5, "product": "N1(CCOCC1)C1=CC(=C(C#N)C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.8, "product": "N1(CCOCC1)C1=CC(=C(C#N)C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A mixture of 2,4-dinitrobenzonitrile 4.20 g (21.75 mmol) and morpholine 5.7 mL (66.0 mmol) in N,N-dimethyformamide 20 mL was stirred at room temperature for 20 hours. The reaction mixture was poured into water. The precipitate was collected and washed with water to give the title compound 4.20 g as orange solid. Yield ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HO- | CN(C=O)C | null | 20 | C1COCCN1.N#Cc1ccc([N+](=O)[O-])cc1[N+](=O)[O-]>CN(C=O)C>N#Cc1ccc(N2CCOCC2)cc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-75c0286756144202a871cac29c39630a | N#Cc1ccc(N2CCOCC2)cc1[N+](=O)[O-]>>N#Cc1ccc(N2CCOCC2)cc1N | O.O.[Sn](Cl)Cl.N1(CCOCC1)C1=CC(=C(C#N)C=C1)[N+](=O)[O-].[OH-].[Na+]>>NC1=C(C#N)C=CC(=C1)N1CCOCC1 | O=[N+:15]([O-])[c:14]1[c:3]([C:2]#[N:1])[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13][c:14]1[NH2:15] | N#Cc1ccc(N2CCOCC2)cc1[N+](=O)[O-] | N#Cc1ccc(N2CCOCC2)cc1N | null | null | Cl | 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] | 95.7 | [{"value": 95.0, "product": "NC1=C(C#N)C=CC(=C1)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.7, "product": "NC1=C(C#N)C=CC(=C1)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a cooled mixture of tin(II) chloride dihydrate 12.8 g (56.7 mmol) in conc. HCl 40 mL with ice bath was added 4-(morpholin-4-yl)-2-nitrobenzonitrile 4.20 g (16.09 mmol) and stirred at room temperature for 2 hours. The reaction mixture was poured into diluted NaOH solution and extracted into ethyl acetate. The organic... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1COCC[NH]1 | Other | Cl | null | 2 | N#Cc1ccc(N2CCOCC2)cc1[N+](=O)[O-]>Cl>N#Cc1ccc(N2CCOCC2)cc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b16afaa5ee724016950e8ef678ff18d8 | N#Cc1ccc(N2CCOCC2)cc1N.NCCN>>Nc1cc(N2CCOCC2)ccc1C1=NCCN1 | NC1=C(C#N)C=CC(=C1)N1CCOCC1.P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3.C(CN)N>>N1C(=NCC1)C1=C(C=C(C=C1)N1CCOCC1)N | [NH2:1][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[C:14]#[N:15].N[CH2:16][CH2:17][NH2:18]>>[NH2:1][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[C:14]1=[N:15][CH2:16][CH2:17][NH:18]1 | N#Cc1ccc(N2CCOCC2)cc1N.NCCN | Nc1cc(N2CCOCC2)ccc1C1=NCCN1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 44acbf70f9cc2ac0a229971bc6e7c77034e28fcd162de6449941e21cd576fef7 | e5ee524a9b0e5a2fe21766a24b1795b0d2b08a43f7dda8289a0ee59c7b4777e1 | c1cc(N2CCOCC2)ccc1C1=NCCN1 | N-[CH2;D2;+0:1]-[C:2]-[NH2;D1;+0:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[C;H0;D3;+0:5]1=[N;H0;D2;+0:4]-[CH2;D2;+0:1]-[C:2]-[NH;D2;+0:3]-1):[c:8] | 83.5 | [{"value": 83.5, "product": "N1C(=NCC1)C1=C(C=C(C=C1)N1CCOCC1)N", "details": "PERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 16 | HOUR | To a solution of 2-amino-4-(morpholin-4-yl)benzonitrile 3.65 g (18.0 mmol) in ethylenediamine 20 mL was added phosphorus pentasulfide 4.00 mg (0.018 mmol) and stirred at 140° C. for 16 hours. After cooling to room temperature, the solvent was evaporated. The residue was washed with water and diethyl ether to give the t... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Primary amine | Secondary amine | null | C1=NCCN1 | c1ccccc1.C1COCC[NH]1.C1=NCCN1 | Other | null | 140 | 16 | N#Cc1ccc(N2CCOCC2)cc1N.NCCN>>Nc1cc(N2CCOCC2)ccc1C1=NCCN1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ff01c9b644340078f0d6fba3c556412 | N#CBr.Nc1cc(N2CCOCC2)ccc1C1=NCCN1>>Br.NC1=Nc2cc(N3CCOCC3)ccc2C2=NCCN12 | N1C(=NCC1)C1=C(C=C(C=C1)N1CCOCC1)N.N#CBr>>Br.N1(CCOCC1)C=1C=CC=2C=3N(C(=NC2C1)N)CCN3 | [Br:1][C:3]#[N:2].[NH2:4][c:5]1[cH:6][c:7]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[cH:14][cH:15][c:16]1[C:17]1=[N:18][CH2:19][CH2:20][NH:21]1>>[BrH:1].[NH2:2][C:3]1=[N:4][c:5]2[cH:6][c:7]([N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[cH:14][cH:15][c:16]2[C:17]2=[N:18][CH2:19][CH2:20][N:21]12 | N#CBr.Nc1cc(N2CCOCC2)ccc1C1=NCCN1 | Br.NC1=Nc2cc(N3CCOCC3)ccc2C2=NCCN12 | null | null | CC(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 4efb46b182c6a436385a7238277900d32b3e1532cf788ff4f8cd430833519b7c | b57bdbe728a8b92000f0fde9e9afe3b122c54cb15f189300cc8bbbea277457ba | C1=Nc2cc(N3CCOCC3)ccc2C2=NCCN12 | [Br;H0;D1;+0:1]-[C;H0;D2;+0:2]#[N;H0;D1;+0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]-[C:8]1=[#7:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[BrH;D0;+0:1].[NH2;D1;+0:3]-[C;H0;D3;+0:2]1=[N;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]-[C:8]2=[#7:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-2-1 | 77.5 | [{"value": 77.5, "product": "Br.N1(CCOCC1)C=1C=CC=2C=3N(C(=NC2C1)N)CCN3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.3, "product": "Br.N1(CCOCC1)C=1C=CC=2C=3N(C(=NC2C1)N)CCN3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | To a suspension of [2-(4,5-dihydro-1H-imidazol-2-yl)-5-(morpholin-4-yl)phenyl]amine 3.60 g (14.6 mmol) in 2-propanol 20 mL was added cyanogen bromide 2.32 g (21.9mmol) portionwise at 0° C. and stirred at 100° C. for 2 hours. After cooling to room temperature, the precipitate was collected and washed with diethyl ether ... | 10.6084/m9.figshare.5104873.v1 | null | Haloalkyne.Nitrile.Primary amine.Secondary amine | Primary amine.Tertiary amine | C1=NCCN1 | C1=Nc2ccccc2C2=NCCN12 | C1COCC[NH]1.C1=Nc2ccccc2C2=NCCN12 | null | CC(C)O | 100 | 2 | N#CBr.Nc1cc(N2CCOCC2)ccc1C1=NCCN1>CC(C)O>Br.NC1=Nc2cc(N3CCOCC3)ccc2C2=NCCN12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5308777b6f2a48389bc80056f7c09538 | CC(=O)OC(C)=O.Nc1ccc(C(=O)O)cn1>>CC(=O)Nc1ccc(C(=O)O)cn1 | Cl.NC1=NC=C(C(=O)O)C=C1.C(C)(=O)OC(C)=O.C(C)(=O)OCC>>C(C)(=O)NC1=NC=C(C(=O)O)C=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][n:13]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[cH:12][n:13]1 | CC(=O)OC(C)=O.Nc1ccc(C(=O)O)cn1 | CC(=O)Nc1ccc(C(=O)O)cn1 | null | null | N1=CC=CC=C1 | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccncc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8] | 26 | [{"value": 26.0, "product": "C(C)(=O)NC1=NC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.9, "product": "C(C)(=O)NC1=NC=C(C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 24 | HOUR | A mixture of 6-aminonicotinic acid 5.00 g (36.5 mmol) and acetic anhydride 3.80 mL (40.2 mmol) in pyridine 30 mL was stirred at 140° C. for 24 hours. To the reaction mixture was added ethyl acetate and acidified with diluted HCl solution to pH 2. The organic layer was washed with water and brine, dried over MgSO4, filt... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccncc1 | HO- | N1=CC=CC=C1 | 140 | 24 | CC(=O)OC(C)=O.Nc1ccc(C(=O)O)cn1>N1=CC=CC=C1>CC(=O)Nc1ccc(C(=O)O)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4cb9f5ffb60e4973b48f0fd65fd117a7 | CC(=O)Nc1ccc(C(=O)O)cn1.NC1=Nc2cc(N3CCOCC3)ccc2C2=NCCN12>>CC(=O)Nc1ccc(C(=O)NC2=Nc3cc(N4CCOCC4)ccc3C3=NCCN23)cn1 | Br.N1(CCOCC1)C=1C=CC=2C=3N(C(=NC2C1)N)CCN3.C(C)(=O)NC1=NC=C(C(=O)O)C=C1.C(C)(C)N(C(C)C)CC.C(=O)(O)[O-].[Na+]>>C(C)(=O)NC1=NC=C(C(=O)NC2=NC=3C=C(C=CC3C=3N2CCN3)N3CCOCC3)C=C1 | O[C:9]([c:8]1[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[n:32][cH:31]1)=[O:10].[NH2:11][C:12]1=[N:13][c:14]2[cH:15][c:16]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[cH:23][cH:24][c:25]2[C:26]2=[N:27][CH2:28][CH2:29][N:30]12>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[NH:11][C:12]2=[N:13][c:... | CC(=O)Nc1ccc(C(=O)O)cn1.NC1=Nc2cc(N3CCOCC3)ccc2C2=NCCN12 | CC(=O)Nc1ccc(C(=O)NC2=Nc3cc(N4CCOCC4)ccc3C3=NCCN23)cn1 | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NC1=Nc2cc(N3CCOCC3)ccc2C2=NCCN12)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[#7:8]=[C:9]-[#7:10](-[C:11])-[C:12](-[NH2;D1;+0:13])=[#7:14]-[c:15]>>[#7:8]=[C:9]-[#7:10](-[C:11])-[C:12](-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7])=[#7:14]-[c:15] | 31.6 | [{"value": 31.6, "product": "C(C)(=O)NC1=NC=C(C(=O)NC2=NC=3C=C(C=CC3C=3N2CCN3)N3CCOCC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.6, "product": "C(C)(=O)NC1=NC=C(C(=O)NC2=NC=3C=C(C=CC3C=3N2CCN3)N3CCOCC3)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 16 | HOUR | To a mixture of 8-(morpholin-4-yl)-2,3-dihydroimidazo[1,2-c]quinazolin-5-amine hydrobromide 105.7 mg (0.30 mmol), 6-(acetamido)nicotinic acid 81.1 mg (0.45 mmol) and N,N-diisopropylethylamine 0.26 mL (1.50 mmol) in N,N-dimethylformamide 2 mL was added PyBOP((1H-1,2,3-benzotriazol-1-yloxy)(tripyrrolidin-1-yl)-phosphoniu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.C1COCC[NH]1.C1=Nc2ccccc2C2=NCCN12 | HO- | CN(C=O)C | 90 | 16 | CC(=O)Nc1ccc(C(=O)O)cn1.NC1=Nc2cc(N3CCOCC3)ccc2C2=NCCN12>CN(C=O)C>CC(=O)Nc1ccc(C(=O)NC2=Nc3cc(N4CCOCC4)ccc3C3=NCCN23)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2e64b0ca6e1142e8a6da646352088218 | Cl>>Cl | C(C)(=O)NC1=NC=C(C(=O)NC2=NC=3C=C(C=CC3C=3N2CCN3)N3CCOCC3)C=C1.Cl>>Cl.C(C)(=O)NC1=NC=C(C(=O)NC2=NC=3C=C(C=CC3C=3N2CCN3)N3CCOCC3)C=C1 | [ClH:33]>>[ClH:33] | Cl | Cl | null | null | O1CCOCC1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 78 | [{"value": 78.0, "product": "Cl.C(C)(=O)NC1=NC=C(C(=O)NC2=NC=3C=C(C=CC3C=3N2CCN3)N3CCOCC3)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | To a mixture of 6-(acetamido)-N-[8-(morpholin-4-yl)-2,3-dihydroimidazo[1,2-c]-quinazolin-5-yl]nicotinamide (Example 2-3) 20.0 mg (0.046 mmol) in 1,4-dioxane 1.5 mL was added 4N HCl in 1,4-dioxane 0.5 mL and stirred at room temperature for 40 minutes. The precipitate was collected and washed with diethyl ether to give t... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O1CCOCC1 | null | 0.666667 | Cl>O1CCOCC1>Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-658fe66ff5b84eeab89de6bd1ec70c73 | COc1ccc2c(c1)N=C(NC(=O)c1cccnc1)N1CCN=C21>>O=C(NC1=Nc2cc(O)ccc2C2=NCCN12)c1cccnc1 | COC=1C=CC=2C=3N(C(=NC2C1)NC(C1=CN=CC=C1)=O)CCN3.[S-2].[Na+].[Na+]>>OC=1C=CC=2C=3N(C(=NC2C1)NC(C1=CN=CC=C1)=O)CCN3 | C[O:9][c:8]1[cH:7][c:6]2[c:12]([cH:11][cH:10]1)[C:13]1=[N:14][CH2:15][CH2:16][N:17]1[C:4]([NH:3][C:2](=[O:1])[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1)=[N:5]2>>[O:1]=[C:2]([NH:3][C:4]1=[N:5][c:6]2[cH:7][c:8]([OH:9])[cH:10][cH:11][c:12]2[C:13]2=[N:14][CH2:15][CH2:16][N:17]12)[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1 | COc1ccc2c(c1)N=C(NC(=O)c1cccnc1)N1CCN=C21 | O=C(NC1=Nc2cc(O)ccc2C2=NCCN12)c1cccnc1 | null | null | CN1C(CCC1)=O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(NC1=Nc2ccccc2C2=NCCN12)c1cccnc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 69.9 | [{"value": 69.9, "product": "OC=1C=CC=2C=3N(C(=NC2C1)NC(C1=CN=CC=C1)=O)CCN3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.9, "product": "OC=1C=CC=2C=3N(C(=NC2C1)NC(C1=CN=CC=C1)=O)CCN3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | null | null | A suspension of N-(8-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)nicotinamide (example 2-22) 3.50 g (10.9 mmol) and sodium sulfide 4.25 g (54.5 mmol) in 1-methyl-2-pyrrolidinone 10 mL was heated to 160° C. for 4 hours (LC-MS indicated complete consumption of the starting material). The mixture was cooled to room t... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1=Nc2ccccc2C2=NCCN12.c1ccncc1 | Other | CN1C(CCC1)=O | 160 | null | COc1ccc2c(c1)N=C(NC(=O)c1cccnc1)N1CCN=C21>CN1C(CCC1)=O>O=C(NC1=Nc2cc(O)ccc2C2=NCCN12)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-69ebf4b0b9b8479bacbc0dd817d5ce7f | BrCCn1cccc1.O=C(NC1=Nc2cc(O)ccc2C2=NCCN12)c1cccnc1>>O=C(NC1=Nc2cc(OCCn3cccc3)ccc2C2=NCCN12)c1cccnc1 | OC=1C=CC=2C=3N(C(=NC2C1)NC(C1=CN=CC=C1)=O)CCN3.BrCCN1C=CC=C1.C([O-])([O-])=O.[K+].[K+]>>N1(C=CC=C1)CCOC=1C=CC=2C=3N(C(=NC2C1)NC(C1=CN=CC=C1)=O)CCN3 | Br[CH2:10][CH2:11][n:12]1[cH:13][cH:14][cH:15][cH:16]1.[O:1]=[C:2]([NH:3][C:4]1=[N:5][c:6]2[cH:7][c:8]([OH:9])[cH:17][cH:18][c:19]2[C:20]2=[N:21][CH2:22][CH2:23][N:24]12)[c:25]1[cH:26][cH:27][cH:28][n:29][cH:30]1>>[O:1]=[C:2]([NH:3][C:4]1=[N:5][c:6]2[cH:7][c:8]([O:9][CH2:10][CH2:11][n:12]3[cH:13][cH:14][cH:15][cH:16]3)... | BrCCn1cccc1.O=C(NC1=Nc2cc(O)ccc2C2=NCCN12)c1cccnc1 | O=C(NC1=Nc2cc(OCCn3cccc3)ccc2C2=NCCN12)c1cccnc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=C(NC1=Nc2cc(OCCn3cccc3)ccc2C2=NCCN12)c1cccnc1 | Br-[CH2;D2;+0:1]-[C:2]-[#7;a:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7;a:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 54 | [{"value": 54.0, "product": "N1(C=CC=C1)CCOC=1C=CC=2C=3N(C(=NC2C1)NC(C1=CN=CC=C1)=O)CCN3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.2, "product": "N1(C=CC=C1)CCOC=1C=CC=2C=3N(C(=NC2C1)NC(C1=CN=CC=C1)=O)CCN3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | The suspension of N-(8-Hydroxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)nicotinamide (example 2-1) 70.0 mg (0.23 mmol), N-(2-bromoethyl)pyrrole 47.6 mg (0.27 mmol) and potassium carbonate 126 mg (0.91 mmol) in N,N-dimethylformamide 5 mL was heated in a sealed tube to 120° C. for 3 hours. The reaction mixture was concen... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1cc[nH]c1.C1=Nc2ccccc2C2=NCCN12.c1ccncc1 | HBr | CN(C=O)C | 120 | null | BrCCn1cccc1.O=C(NC1=Nc2cc(O)ccc2C2=NCCN12)c1cccnc1>CN(C=O)C>O=C(NC1=Nc2cc(OCCn3cccc3)ccc2C2=NCCN12)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f5aca1aaf5c45609d0e4cb92dc33cde | Nc1ccccc1C1=NCCN1>>Nc1ccccc1-c1ncc[nH]1 | Br.N1C(=NCC1)C1=C(N)C=CC=C1.Cl.NO>>N1C(=NC=C1)C1=C(N)C=CC=C1 | [NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8]1=[N:9][CH2:10][CH2:11][NH:12]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[n:9][cH:10][cH:11][nH:12]1 | Nc1ccccc1C1=NCCN1 | Nc1ccccc1-c1ncc[nH]1 | null | [O-2].[O-2].[Mn+4] | O | Aromatic Heterocycle Formation | OtherReaction | 1720d4a06439f89550ac112855f8fefe948006b35f1e0b2c33f34624a268b0bc | e7755fc26c2ee565703ce58f70e69353872b755c86481e99a670e0a6a3491119 | c1ccc(-c2ncc[nH]2)cc1 | [N;D1;H2:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[C;H0;D3;+0:5]1=[N;H0;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[NH;D2;+0:9]-1):[c:10]:[c:11]>>[N;D1;H2:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[nH;D2;+0:9]:1):[c:10]:[c:11] | 61 | [{"value": 61.0, "product": "N1C(=NC=C1)C1=C(N)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.7, "product": "N1C(=NC=C1)C1=C(N)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 2-(4,5-dihydro-1H-imidazol-2-yl)aniline hydrobromide (50.0 mg, 0.207 mmol) and manganese dioxide (170 mg, 1.96 mmol) in N,N′-dimethylpropylenurea (2.0 mL) was heated at 150. (bath temp.). After 1 hour, the reaction mixture was cooled to room temperature, poured into a solution of hydroxylamine hydrochlorid... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | null | C1=NCCN1 | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | null | [O-2].[O-2].[Mn+4].O | null | 1 | Nc1ccccc1C1=NCCN1>[O-2].[O-2].[Mn+4].O>Nc1ccccc1-c1ncc[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3108ef504c664b249420a78df7493c47 | CCOC(=O)CC(=O)[O-].O=C(O)c1cccs1>>CCOC(=O)CC(=O)c1cccs1 | C(=O)(N1C=NC=C1)N1C=NC=C1.S1C(=CC=C1)C(=O)O.[Cl-].[Mg+2].[Cl-].C(C)OC(CC(=O)[O-])=O>>O=C(CC(=O)OCC)C=1SC=CC1 | O=C([O-])[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].O[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][s:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][s:13]1 | CCOC(=O)CC(=O)[O-].O=C(O)c1cccs1 | CCOC(=O)CC(=O)c1cccs1 | null | null | O1CCCC1.O | C-C Coupling | OtherReaction | 6e144dbbf281048ca902de5a0a54b731c99776ef982e7e4aab4fdee308ea4d06 | d5654c9a84fc42e383a200090b60ea1c499fce894824745135207b080d8463d3 | c1ccsc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].O=C(-[O-])-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 78.1 | [{"value": 78.0, "product": "O=C(CC(=O)OCC)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.1, "product": "O=C(CC(=O)OCC)C=1SC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of 2-thiophenecarboxylic acid (6.48 g, 50.57 mmol) in tetrahydrofurane (100 ml) at 5. was added 1,1′-Carbonyldiimidazole (8.61 g, 53.09 mmol) by portions. The mixture was allowed to warm to room temperature, and the stirring was continued for 1 hour. The reaction mixture was added into a suspension mixt... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ketone | null | null | c1ccsc1 | HO- | O1CCCC1.O | null | 1 | CCOC(=O)CC(=O)[O-].O=C(O)c1cccs1>O1CCCC1.O>CCOC(=O)CC(=O)c1cccs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e1a974e612b7416093fa8922a5458776 | CCOC(=O)CC(=O)c1cccs1.Nc1ccccc1-c1ncc[nH]1>>O/C(=C\c1nc2ccccc2c2nccn12)c1cccs1 | N1C(=NC=C1)C1=C(N)C=CC=C1.C(C)OC(CC(C=1SC=CC1)=O)=O>>N=1C=CN2C(=NC=3C=CC=CC3C21)\C=C(/O)\C=2SC=CC2 | CCO[C:4](=O)[CH2:3][C:2](=[O:1])[c:17]1[cH:18][cH:19][cH:20][s:21]1.[NH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1-[c:12]1[n:13][cH:14][cH:15][nH:16]1>>[OH:1]/[C:2](=[CH:3]\[c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[c:12]2[n:13][cH:14][cH:15][n:16]12)[c:17]1[cH:18][cH:19][cH:20][s:21]1 | CCOC(=O)CC(=O)c1cccs1.Nc1ccccc1-c1ncc[nH]1 | O/C(=C\c1nc2ccccc2c2nccn12)c1cccs1 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 63958d2e2fb7ad80138888731d61c3a8860d2ea9d68a16d9e81ad2f0f1e9bfea | 9ae1a6c835f6a334417a3d822f9365c0b2c2f1144b3c1761cf87e8e2433344ba | C(=Cc1nc2ccccc2c2nccn12)c1cccs1 | C-C-O-[C;H0;D3;+0:1](=O)-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[#16;a:7]:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[c;H0;D3;+0:13]1:[#7;a:14]:[c:15]:[c:16]:[nH;D2;+0:17]:1):[c:18]:[c:19]>>[OH;D1;+0:4]/[C;H0;D3;+0:3](=[CH;D2;+0:2]\[c;H0;D3;+0:1]1:[n;H0;D2;+0:9]:[c:10](:[c:11]):[c;H0;D3;+... | 33.2 | [{"value": 33.0, "product": "N=1C=CN2C(=NC=3C=CC=CC3C21)\\C=C(/O)\\C=2SC=CC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.2, "product": "N=1C=CN2C(=NC=3C=CC=CC3C21)\\C=C(/O)\\C=2SC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-(1H-imidazol-2-yl)aniline (60.0 mg, 0.38 mmol), ethyl3-oxo-3-(2-thienyl)propanoate (74.7 mg, 0.38 mmol) and p-tolenesulfonicacid monohydrate (36.1 mg, 0.19 mmol) in toluene (30 ml) was heated at reflux for 2 hours. After cooling to room temperature, the reaction mixture was poured into aqueous saturate N... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Enol | c1ccccc1.c1c[nH]cn1 | c1ccc2c(c1)ncn1ccnc21 | c1ccc2c(c1)ncn1ccnc21.c1ccsc1 | HO- | C1(=CC=CC=C1)C | null | null | CCOC(=O)CC(=O)c1cccs1.Nc1ccccc1-c1ncc[nH]1>C1(=CC=CC=C1)C>O/C(=C\c1nc2ccccc2c2nccn12)c1cccs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-acb5f2eb7f7347b5a7b2e2062208c006 | O/C(=C\c1nc2ccccc2c2nccn12)c1cccs1>>O/C(=C\c1nc2ccccc2c2nccn12)c1cccs1 | N=1C=CN2C(=NC=3C=CC=CC3C21)\C=C(/O)\C=2SC=CC2.Cl>>Cl.N=1C=CN2C(=NC=3C=CC=CC3C21)\C=C(/O)\C=2SC=CC2 | [OH:2]/[C:3](=[CH:4]\[c:5]1[n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[c:13]2[n:14][cH:15][cH:16][n:17]12)[c:18]1[cH:19][cH:20][cH:21][s:22]1>>[OH:2]/[C:3](=[CH:4]\[c:5]1[n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[c:13]2[n:14][cH:15][cH:16][n:17]12)[c:18]1[cH:19][cH:20][cH:21][s:22]1 | O/C(=C\c1nc2ccccc2c2nccn12)c1cccs1 | O/C(=C\c1nc2ccccc2c2nccn12)c1cccs1 | null | null | O1CCOCC1.C(Cl)(Cl)Cl.C(C)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C(=Cc1nc2ccccc2c2nccn12)c1cccs1 | null | null | [] | null | null | null | null | To a solution of (Z-2-imidazo[1,2-c]quinazolin-5-yl-1-(2-thienyl)ethenol (0.06 g, 0.07 mmol) in chloroform (1.0 ml) was added a 4N solution of HCl in 1,4-dioxane (0.5 ml). The mixture was diluted with ethyl ether, and the resulting precipitate was collected by filtration, washed with ethyl ether, and dried under reduce... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)ncn1ccnc21.c1ccsc1 | null | O1CCOCC1.C(Cl)(Cl)Cl.C(C)OCC | null | null | O/C(=C\c1nc2ccccc2c2nccn12)c1cccs1>O1CCOCC1.C(Cl)(Cl)Cl.C(C)OCC>O/C(=C\c1nc2ccccc2c2nccn12)c1cccs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-011aa2a49c6944ec819f2658840ab803 | N#CBr.Nc1ccccc1-c1ncc[nH]1>>Br.Nc1nc2ccccc2c2nccn12 | O.N1C(=NC=C1)C1=C(N)C=CC=C1.N#CBr>>Br.N=1C=CN2C(=NC=3C=CC=CC3C21)N | [Br:1][C:3]#[N:2].[NH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[n:12][cH:13][cH:14][nH:15]1>>[BrH:1].[NH2:2][c:3]1[n:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[c:11]2[n:12][cH:13][cH:14][n:15]12 | N#CBr.Nc1ccccc1-c1ncc[nH]1 | Br.Nc1nc2ccccc2c2nccn12 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | a899cda9eef44e1f98b1288eb7978bfd14dda01a38a843c5160b17d1f66d0e85 | ecfe44f67364ffe37819d7701600d32ae8d468ee41926a02afd56a1f6dc0756e | c1ccc2c(c1)ncn1ccnc21 | [Br;H0;D1;+0:1]-[C;H0;D2;+0:2]#[N;H0;D1;+0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1):[c:13]:[c:14]>>[BrH;D0;+0:1].[NH2;D1;+0:3]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c;H0;D3;+0:7](:[c:13]:[c:14]):[c;H0;D3;+0:8]2:[#7;a:9]:[c:10]:[c:11]:[n;H0;D3;+0:12]:... | 61 | [{"value": 61.0, "product": "Br.N=1C=CN2C(=NC=3C=CC=CC3C21)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.6, "product": "Br.N=1C=CN2C(=NC=3C=CC=CC3C21)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 2-(1H-imidazol-2-yl)aniline (0.06 g. 0.38 mmol) in methanol (3 ml) was added cyanogen bromide (0.05 g, 0.45 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting precipitate was collected by filtration, washed with acetone,... | 10.6084/m9.figshare.5104873.v1 | null | Haloalkyne.Nitrile.Primary amine | Primary amine | c1ccccc1.c1c[nH]cn1 | c1ccc2c(c1)ncn1ccnc21 | c1ccc2c(c1)ncn1ccnc21 | null | CO | null | 8 | N#CBr.Nc1ccccc1-c1ncc[nH]1>CO>Br.Nc1nc2ccccc2c2nccn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0673f2d150e94a16ba8313c89eab5b8a | Nc1nc2ccccc2c2nccn12.O=C(O)c1cccnc1>>O=C(Nc1nc2ccccc2c2nccn12)c1cccnc1 | C(C)(C)N(C(C)C)CC.Br.N=1C=CN2C(=NC=3C=CC=CC3C21)N.C(C1=CN=CC=C1)(=O)O.C(=O)(O)[O-].[Na+].F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N2CCCC2)(N2CCCC2)N2CCCC2>>N=1C=CN2C(=NC=3C=CC=CC3C21)NC(C2=CN=CC=C2)=O | [NH2:3][c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[c:12]2[n:13][cH:14][cH:15][n:16]12.O[C:2](=[O:1])[c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]1>>[O:1]=[C:2]([NH:3][c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[c:12]2[n:13][cH:14][cH:15][n:16]12)[c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]1 | Nc1nc2ccccc2c2nccn12.O=C(O)c1cccnc1 | O=C(Nc1nc2ccccc2c2nccn12)c1cccnc1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1nc2ccccc2c2nccn12)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[#7;a:10]:[c:11]):[#7;a:12]1:[c:13]:[#7;a:14]:[c:15]:[c:16]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[#7;a:10]:[c:11]):[#7;a:12]1:[c:13]:[#7;a:14]:[c:15]:[c:16]:1)-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 39.5 | [{"value": 39.0, "product": "N=1C=CN2C(=NC=3C=CC=CC3C21)NC(C2=CN=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.5, "product": "N=1C=CN2C(=NC=3C=CC=CC3C21)NC(C2=CN=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a mixture of imidazo[1,2-c]quinazolin-5-amine hydrobromide (93 mg, 0.35 mmol) and nicotinic acid (124 mg, 1.01 mmol) and DMF (2.5 ml) at room temperature was added benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (525 mg, 1.01 mmol) followed by N,N-diisopropylethyl amine (0.264 ml, 1.51 mmol),... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)ncn1ccnc21.c1ccncc1 | HO- | CN(C)C=O | null | 6 | Nc1nc2ccccc2c2nccn12.O=C(O)c1cccnc1>CN(C)C=O>O=C(Nc1nc2ccccc2c2nccn12)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-78514312fa364253bc66280673ba10bb | O=C(Nc1nc2ccccc2c2nccn12)c1cccnc1>>O=C(Nc1nc2ccccc2c2nccn12)c1cccnc1 | N=1C=CN2C(=NC=3C=CC=CC3C21)NC(C2=CN=CC=C2)=O.Cl>>Cl.N=1C=CN2C(=NC=3C=CC=CC3C21)NC(C2=CN=CC=C2)=O | [O:2]=[C:3]([NH:4][c:5]1[n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[c:13]2[n:14][cH:15][cH:16][n:17]12)[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1>>[O:2]=[C:3]([NH:4][c:5]1[n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[c:13]2[n:14][cH:15][cH:16][n:17]12)[c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1 | O=C(Nc1nc2ccccc2c2nccn12)c1cccnc1 | O=C(Nc1nc2ccccc2c2nccn12)c1cccnc1 | null | null | O1CCOCC1.CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(Nc1nc2ccccc2c2nccn12)c1cccnc1 | null | 89 | [{"value": 89.0, "product": "Cl.N=1C=CN2C(=NC=3C=CC=CC3C21)NC(C2=CN=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of N-imidazo[1,2-c]quinazolin-5-ylnicotinamide (40 mg, 0.14 mmol) in methanol (20 ml) was added a 4N solution of HCl in 1,4dioxane (0.5 ml). The mixture was concentrated under reduced pressure. The resulting solid was collected by filtration, washed with tetrahydrofurane and dried under reduced pressure t... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)ncn1ccnc21.c1ccncc1 | null | O1CCOCC1.CO | null | null | O=C(Nc1nc2ccccc2c2nccn12)c1cccnc1>O1CCOCC1.CO>O=C(Nc1nc2ccccc2c2nccn12)c1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1b22564fbbbe46659503648c16b91040 | CCOC(C)=O.COC(=O)c1cccc(C)n1>>CCOC(=O)CC(=O)c1cccc(C)n1 | COC(=O)C1=NC(=CC=C1)C.[O-]CC.[Na+].C1(=CC=CC=C1)C.C(C)(=O)OCC>>C(C)OC(CC(=O)C1=NC(=CC=C1)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH3:6].CO[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([CH3:14])[n:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([CH3:14])[n:15]1 | CCOC(C)=O.COC(=O)c1cccc(C)n1 | CCOC(=O)CC(=O)c1cccc(C)n1 | null | null | C(C)(=O)O | C-C Coupling | OtherReaction | 66fad61539a4377b2099bf2b4bbabe7e2e80878fd5eeb84b925f14180416e99f | 53456c3e87e97f512921684f59b54573df1eee9d8c313db55cd612727f50bb31 | c1ccncc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C:7]-[#8:8]-[C:9](-[CH3;D1;+0:10])=[O;D1;H0:11]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:11])-[CH2;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | 112.6 | [{"value": 112.6, "product": "C(C)OC(CC(=O)C1=NC(=CC=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 92 | CELSIUS | 1 | HOUR | Stir a mixture of sodium ethoxide (90 g, 1.32 mol), toluene (0.5 L), and ethyl acetate (0.2 L, 1.98 mol) in a 2 L flask equipped with reflux condenser, mechanical stirrer, and nitrogen inlet. After 1 h, add 6-methyl-pyridine-2-carboxylic acid methyl ester (Cheung, Y, Tetrahedron Lett. 1979, 40, 3809-10; 100 g, 0.66 mol... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone | null | null | c1ccncc1 | HO- | C(C)(=O)O | 92 | 1 | CCOC(C)=O.COC(=O)c1cccc(C)n1>C(C)(=O)O>CCOC(=O)CC(=O)c1cccc(C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0f2ff0e0340d4868a4cf4ff638611eac | CCOC(=O)CC(=O)c1cccc(C)n1.NN1CCCC1=O>>CCOC(=O)CC(=NN1CCCC1=O)c1cccc(C)n1 | Cl.NN1C(CCC1)=O.C(C)OC(CC(=O)C1=NC(=CC=C1)C)=O.N1=CC=CC=C1>>C(C)OC(CC(=NN1C(CCC1)=O)C1=NC(=CC=C1)C)=O | O=[C:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:15]1[cH:16][cH:17][cH:18][c:19]([CH3:20])[n:21]1.[NH2:8][N:9]1[CH2:10][CH2:11][CH2:12][C:13]1=[O:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[N:8][N:9]1[CH2:10][CH2:11][CH2:12][C:13]1=[O:14])[c:15]1[cH:16][cH:17][cH:18][c:19]([CH3:20])[n:21]1 | CCOC(=O)CC(=O)c1cccc(C)n1.NN1CCCC1=O | CCOC(=O)CC(=NN1CCCC1=O)c1cccc(C)n1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | c69945ad5120b7f16dfc8592e8b603d143befb589c2a10c6f629e0efaa5d6175 | ac24b4d8621c562f7730855d0c8234199dd2eb11db82411f7f92e5c96064c963 | O=C1CCCN1N=Cc1ccccn1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[c:7](:[c:8]):[#7;a:9]:[c:10].[C:11]-[#7:12](-[NH2;D1;+0:13])-[C:14](=[O;D1;H0:15])-[C:16]>>[C:11]-[#7:12](-[N;H0;D2;+0:13]=[C;H0;D3;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[c:7](:[c:8]):[#7;a:9]:[c:10])-[C:14](=[O;D1;H0:15])-[C:16] | null | [] | null | null | 20 | HOUR | Add 1-aminopyrrolidin-2-one hydrochloride (Zubek, A. Z. Chem. 1969, 9(2), 58; 99.4 g, 0.73 mol) to a 3 L flask equipped with mechanical stirrer and nitrogen inlet. Add 3-[6-methyl-(pyridin-2-yl)]-3-oxo-propionic acid ethyl ester (Preparation 1, Part A; 154 g, 0.66 mol), and pyridine (280 mL). Stir the reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ketone | Hydrazone amide | null | null | C1CC[NH]C1.c1ccncc1 | HO- | O | null | 20 | CCOC(=O)CC(=O)c1cccc(C)n1.NN1CCCC1=O>O>CCOC(=O)CC(=NN1CCCC1=O)c1cccc(C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f887793b52fa489e8121b611c8ce465a | CCOC(=O)CC(=NN1CCCC1=O)c1cccc(C)n1>>Cc1cccc(-c2nn3c(c2C(=O)O)CCC3)n1 | Cl.[O-]CC.[Na+].C1(=CC=CC=C1)C.C(C)OC(CC(=NN1C(CCC1)=O)C1=NC(=CC=C1)C)=O>>CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C(=O)O | CC[O:14][C:12]([CH2:11][C:7]([c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:18]1)=[N:8][N:9]1[C:10](=O)[CH2:15][CH2:16][CH2:17]1)=[O:13]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([c:11]2[C:12](=[O:13])[OH:14])[CH2:15][CH2:16][CH2:17]3)[n:18]1 | CCOC(=O)CC(=NN1CCCC1=O)c1cccc(C)n1 | Cc1cccc(-c2nn3c(c2C(=O)O)CCC3)n1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 08588c2e42b9bae19c5594fe799e4dcff6d70c9c3733e37bbc82bfbd916a5357 | 56cfff3fccc1aaaa306668ef7b771d2c6c05ea185b1b211d2ac531d8d4734a40 | c1ccc(-c2cc3n(n2)CCC3)nc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[C;H0;D3;+0:5](=[N;H0;D2;+0:6]-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[C:10]-[C;H0;D3;+0:11]-1=O)-[c;H0;D3;+0:12](:[#7;a:13]:[c:14]):[c:15]:[c:16]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c;H0;D3;+0:4]1:[c;H0;D3;+0:11]2:[n;H0;D3;+0:7](:[n;H0;D2;+0:6]:[c;H0;D3;+0:5]:1-[c;H0;D3;+0:12](... | 86 | [{"value": 86.0, "product": "CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.8, "product": "CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | Add sodium ethoxide (90 g, 1.32 mol), toluene (5 L) and 3-[6-methyl-(pyridin-2-yl)]-3-(2-oxo-pyrrolidin-1-ylimino)-propionic acid ethyl ester (Preparation 1, Part B; 201 g, 0.661 mol) to a 22 L flask equipped with a mechanical stirrer, nitrogen inlet and a reflux condenser. Heat the mixture at 100° C. for 24 h then coo... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide.Ester | Carboxylic acid | C1CC[NH]C1 | c1cc2n(n1)CCC2 | c1ccncc1.c1cc2n(n1)CCC2 | HO- | O | 100 | null | CCOC(=O)CC(=NN1CCCC1=O)c1cccc(C)n1>O>Cc1cccc(-c2nn3c(c2C(=O)O)CCC3)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dc745e4b2b464c8493683d19b70aa782 | CC(C)OB(OC(C)C)OC(C)C.Cc1cccc(-c2nn3c(c2Br)CCC3)n1>>Cc1cccc(-c2nn3c(c2B(O)O)CCC3)n1 | BrC1=C2N(N=C1C1=NC(=CC=C1)C)CCC2.B(OC(C)C)(OC(C)C)OC(C)C.C(CCC)[Li]>>CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)B(O)O | CC(C)O[B:12]([O:13]C(C)C)[O:14]C(C)C.Br[c:11]1[c:7](-[c:6]2[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:18]2)[n:8][n:9]2[c:10]1[CH2:15][CH2:16][CH2:17]2>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][n:9]3[c:10]([c:11]2[B:12]([OH:13])[OH:14])[CH2:15][CH2:16][CH2:17]3)[n:18]1 | CC(C)OB(OC(C)C)OC(C)C.Cc1cccc(-c2nn3c(c2Br)CCC3)n1 | Cc1cccc(-c2nn3c(c2B(O)O)CCC3)n1 | null | null | O1CCCC1 | Miscellaneous | Preparation of boronic acids | 01484b4b6e5c07e8f05c1c52e26d37d5ebc3058d2f6fdf307d527d4b21c535b3 | dafd25fbe01879c365f8c874026e570f49824f4bb82016b29d0c5d21aeb58ca3 | c1ccc(-c2cc3n(n2)CCC3)nc1 | Br-[c;H0;D3;+0:1]1:[c:2](:[#7;a:3](:[#7;a:4]:[c:5]:1-[c:6]:[#7;a:7])-[C:8])-[C:9].C-C(-C)-O-[B;H0;D3;+0:10](-[O;H0;D2;+0:11]-C(-C)-C)-[O;H0;D2;+0:12]-C(-C)-C>>[#7;a:7]:[c:6]-[c:5]1:[#7;a:4]:[#7;a:3](:[c:2](:[c;H0;D3;+0:1]:1-[B;H0;D3;+0:10](-[OH;D1;+0:11])-[OH;D1;+0:12])-[C:9])-[C:8] | 73 | [{"value": 73.0, "product": "CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)B(O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.3, "product": "CC1=CC=CC(=N1)C=1C(=C2N(N1)CCC2)B(O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 25 | MINUTE | Place tetrahydrofuran (28.0 mL) in a 100 mL round-bottom flask equipped with a temperature probe, a magnetic stirrer, and a septum and put under a nitrogen atmosphere. Add 3-bromo-2-[6-methyl-(pyridin-2-yl)]-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (Preparation 1, Part D; 1.44 g, 5.18 mmol) and triisopropyl borate (3.10 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | c1cc2n(n1)CCC2 | c1cc2n(n1)CCC2 | c1ccncc1.c1cc2n(n1)CCC2 | HBr | O1CCCC1 | -78 | 0.416667 | CC(C)OB(OC(C)C)OC(C)C.Cc1cccc(-c2nn3c(c2Br)CCC3)n1>O1CCCC1>Cc1cccc(-c2nn3c(c2B(O)O)CCC3)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-553d874a2d1b469fb510ce29b1584ada | CCOC(=O)c1ccccn1.CCOC(C)=O>>CCOC(=O)CC(=O)c1ccccn1 | C(C)OC(=O)C1=NC=CC=C1.[O-]CC.[Na+].C(C)O.C(C)(=O)OCC>>C(C)OC(CC(C1=NC=CC=C1)=O)=O | CCO[C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH3:6]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1 | CCOC(=O)c1ccccn1.CCOC(C)=O | CCOC(=O)CC(=O)c1ccccn1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 66fad61539a4377b2099bf2b4bbabe7e2e80878fd5eeb84b925f14180416e99f | 53456c3e87e97f512921684f59b54573df1eee9d8c313db55cd612727f50bb31 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C:7]-[#8:8]-[C:9](-[CH3;D1;+0:10])=[O;D1;H0:11]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:11])-[CH2;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | 91 | [{"value": 91.0, "product": "C(C)OC(CC(C1=NC=CC=C1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.0, "product": "C(C)OC(CC(C1=NC=CC=C1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | Stir a mixture of sodium ethoxide (360 g, 5.29 mol), toluene (4 L), ethanol (18 mL, 0.265 mol), and ethyl acetate (1.04 L, 10.6 mol) in a 22 L flask equipped with a reflux condenser, nitrogen inlet, and mechanical stirrer. Stir for 1 h as the mixture warms to 26° C. Add pyridine-2-carboxylic acid ethyl ester (Fluka; 40... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone | null | null | c1ccncc1 | HO- | C1(=CC=CC=C1)C | 90 | null | CCOC(=O)c1ccccn1.CCOC(C)=O>C1(=CC=CC=C1)C>CCOC(=O)CC(=O)c1ccccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e17a2d234a344e6ebf59271ff54b42bc | CCOC(=O)CC(=O)c1ccccn1.NN1CCCC1=O>>CCOC(=O)CC(=NN1CCCC1=O)c1ccccn1 | Cl.NN1C(CCC1)=O.C(C)OC(CC(C1=NC=CC=C1)=O)=O.N1=CC=CC=C1>>C(C)OC(CC(C1=NC=CC=C1)=NN1C(CCC1)=O)=O | O=[C:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:15]1[cH:16][cH:17][cH:18][cH:19][n:20]1.[NH2:8][N:9]1[CH2:10][CH2:11][CH2:12][C:13]1=[O:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[N:8][N:9]1[CH2:10][CH2:11][CH2:12][C:13]1=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][n:20]1 | CCOC(=O)CC(=O)c1ccccn1.NN1CCCC1=O | CCOC(=O)CC(=NN1CCCC1=O)c1ccccn1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | c69945ad5120b7f16dfc8592e8b603d143befb589c2a10c6f629e0efaa5d6175 | ac24b4d8621c562f7730855d0c8234199dd2eb11db82411f7f92e5c96064c963 | O=C1CCCN1N=Cc1ccccn1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[c:7](:[c:8]):[#7;a:9]:[c:10].[C:11]-[#7:12](-[NH2;D1;+0:13])-[C:14](=[O;D1;H0:15])-[C:16]>>[C:11]-[#7:12](-[N;H0;D2;+0:13]=[C;H0;D3;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[c:7](:[c:8]):[#7;a:9]:[c:10])-[C:14](=[O;D1;H0:15])-[C:16] | 98 | [{"value": 98.0, "product": "C(C)OC(CC(C1=NC=CC=C1)=NN1C(CCC1)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | Place 1-aminopyrrolidin-2-one hydrochloride (Zubek, A. Z. Chem., 1969, 9(2), 58; 155.6 g, 1.14 mol) in a 3 L flask equipped with mechanical stirrer and nitrogen inlet. Add 3-oxo-3-pyridin-2-yl-propionic acid ethyl ester (Preparation 2, Part A; 200 g, 1.04 mol) and pyridine (400 mL). Stir the reaction mixture at room te... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ketone | Hydrazone amide | null | null | C1CC[NH]C1.c1ccncc1 | HO- | O | null | 20 | CCOC(=O)CC(=O)c1ccccn1.NN1CCCC1=O>O>CCOC(=O)CC(=NN1CCCC1=O)c1ccccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee20f97738554bb087fdded785a6af73 | CCOC(=O)CC(=NN1CCCC1=O)c1ccccn1>>O=C(O)c1c(-c2ccccn2)nn2c1CCC2 | Cl.[O-]CC.[Na+].C1(=CC=CC=C1)C.C(C)OC(CC(C1=NC=CC=C1)=NN1C(CCC1)=O)=O>>N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C(=O)O | CC[O:3][C:2](=[O:1])[CH2:4][C:5]([c:6]1[cH:7][cH:8][cH:9][cH:10][n:11]1)=[N:12][N:13]1[C:14](=O)[CH2:15][CH2:16][CH2:17]1>>[O:1]=[C:2]([OH:3])[c:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][n:11]2)[n:12][n:13]2[c:14]1[CH2:15][CH2:16][CH2:17]2 | CCOC(=O)CC(=NN1CCCC1=O)c1ccccn1 | O=C(O)c1c(-c2ccccn2)nn2c1CCC2 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 08588c2e42b9bae19c5594fe799e4dcff6d70c9c3733e37bbc82bfbd916a5357 | 56cfff3fccc1aaaa306668ef7b771d2c6c05ea185b1b211d2ac531d8d4734a40 | c1ccc(-c2cc3n(n2)CCC3)nc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[C;H0;D3;+0:5](=[N;H0;D2;+0:6]-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[C:10]-[C;H0;D3;+0:11]-1=O)-[c;H0;D3;+0:12](:[#7;a:13]:[c:14]):[c:15]:[c:16]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c;H0;D3;+0:4]1:[c;H0;D3;+0:11]2:[n;H0;D3;+0:7](:[n;H0;D2;+0:6]:[c;H0;D3;+0:5]:1-[c;H0;D3;+0:12](... | 93.2 | [{"value": 93.0, "product": "N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.2, "product": "N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | Add sodium ethoxide (145 g, 2.03 mol), followed by toluene (7 L) and 3-(2-oxo-pyrrolidin-1-ylimino)-3-(pyridin-2-yl)-propionic acid ethyl ester (Preparation 3, Part B; 280 g, 1.02 mol) to a 22 L flask equipped with mechanical stirrer, nitrogen inlet and a reflux condenser. Heat the mixture at 100° C. for 21 h. Cool to ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide.Ester | Carboxylic acid | C1CC[NH]C1 | c1cc2n(n1)CCC2 | c1ccncc1.c1cc2n(n1)CCC2 | HO- | O | 100 | null | CCOC(=O)CC(=NN1CCCC1=O)c1ccccn1>O>O=C(O)c1c(-c2ccccn2)nn2c1CCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3e9fe18969784c3d98b1483d8da8d936 | NC(=O)CCC(=O)NBr.O=C(O)c1c(-c2ccccn2)nn2c1CCC2>>Brc1c(-c2ccccn2)nn2c1CCC2 | N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C(=O)O.C([O-])(O)=O.[Na+].BrNC(CCC(=O)N)=O>>BrC1=C2N(N=C1C1=NC=CC=C1)CCC2 | NC(=O)CCC(=O)N[Br:1].O=C(O)[c:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][cH:8][n:9]2)[n:10][n:11]2[c:12]1[CH2:13][CH2:14][CH2:15]2>>[Br:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][cH:8][n:9]2)[n:10][n:11]2[c:12]1[CH2:13][CH2:14][CH2:15]2 | NC(=O)CCC(=O)NBr.O=C(O)c1c(-c2ccccn2)nn2c1CCC2 | Brc1c(-c2ccccn2)nn2c1CCC2 | null | null | O.CN(C)C=O.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | 8b8c70d4e8bb4e0f48d8bd7b9fb1eea054fb2a9e5d3234fd49918ae3d5edf1a0 | 7152e548e20ab177ec9c36dcbd6278f9362f912f2d7a61ce80771f344eb64217 | c1ccc(-c2cc3n(n2)CCC3)nc1 | N-C(=O)-C-C-C(=O)-N-[Br;H0;D1;+0:1].O-C(=O)-[c;H0;D3;+0:2]1:[c:3](:[#7;a:4](:[#7;a:5]:[c:6]:1-[c:7]:[#7;a:8])-[C:9])-[C:10]>>[#7;a:8]:[c:7]-[c:6]1:[#7;a:5]:[#7;a:4](:[c:3](:[c;H0;D3;+0:2]:1-[Br;H0;D1;+0:1])-[C:10])-[C:9] | 70.5 | [{"value": 70.0, "product": "BrC1=C2N(N=C1C1=NC=CC=C1)CCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.5, "product": "BrC1=C2N(N=C1C1=NC=CC=C1)CCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Stir a mixture of 2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid (Preparation 2C; 2 g, 8.7 mmol), sodium bicarbonate (3.3 g, 38.4 mmol), and N-bromosuccinamide (1.7 g, 9.6 mmol) in DMF (50 mL) at room temperature for 2 h. Dilute the crude mixture with water (50 mL) and ethyl acetate (100 mL). ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amide.Secondary amide | Aromatic halide | c1cc2n(n1)CCC2 | c1cc2n(n1)CCC2 | c1ccncc1.c1cc2n(n1)CCC2 | HO- | O.CN(C)C=O.C(C)(=O)OCC | null | null | NC(=O)CCC(=O)NBr.O=C(O)c1c(-c2ccccn2)nn2c1CCC2>O.CN(C)C=O.C(C)(=O)OCC>Brc1c(-c2ccccn2)nn2c1CCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6b50a2bbd3e14c1a869752d9e1f164f9 | Brc1c(-c2ccccn2)nn2c1CCC2.CC(C)OB(OC(C)C)OC(C)C>>OB(O)c1c(-c2ccccn2)nn2c1CCC2 | BrC1=C2N(N=C1C1=NC=CC=C1)CCC2.B(OC(C)C)(OC(C)C)OC(C)C.C(CCC)[Li]>>N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)B(O)O | Br[c:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][n:11]2)[n:12][n:13]2[c:14]1[CH2:15][CH2:16][CH2:17]2.CC(C)O[B:2]([O:1]C(C)C)[O:3]C(C)C>>[OH:1][B:2]([OH:3])[c:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][n:11]2)[n:12][n:13]2[c:14]1[CH2:15][CH2:16][CH2:17]2 | Brc1c(-c2ccccn2)nn2c1CCC2.CC(C)OB(OC(C)C)OC(C)C | OB(O)c1c(-c2ccccn2)nn2c1CCC2 | null | null | O1CCCC1 | Miscellaneous | Preparation of boronic acids | 01484b4b6e5c07e8f05c1c52e26d37d5ebc3058d2f6fdf307d527d4b21c535b3 | dafd25fbe01879c365f8c874026e570f49824f4bb82016b29d0c5d21aeb58ca3 | c1ccc(-c2cc3n(n2)CCC3)nc1 | Br-[c;H0;D3;+0:1]1:[c:2](:[#7;a:3](:[#7;a:4]:[c:5]:1-[c:6]:[#7;a:7])-[C:8])-[C:9].C-C(-C)-O-[B;H0;D3;+0:10](-[O;H0;D2;+0:11]-C(-C)-C)-[O;H0;D2;+0:12]-C(-C)-C>>[#7;a:7]:[c:6]-[c:5]1:[#7;a:4]:[#7;a:3](:[c:2](:[c;H0;D3;+0:1]:1-[B;H0;D3;+0:10](-[OH;D1;+0:11])-[OH;D1;+0:12])-[C:9])-[C:8] | 55 | [{"value": 55.0, "product": "N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)B(O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.8, "product": "N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)B(O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 25 | MINUTE | Place tetrahydrofuran (60.0 mL) in a 100 mL round-bottom flask equipped with a temperature probe, a magnetic stirrer, and a septum and put under a nitrogen atmosphere. Add 3-bromo-2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (Preparation 3, Part D; 3.00 g, 11.4 mmol) and triisopropyl borate (6.80 mL, 29.5 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | c1cc2n(n1)CCC2 | c1cc2n(n1)CCC2 | c1ccncc1.c1cc2n(n1)CCC2 | HBr | O1CCCC1 | -78 | 0.416667 | Brc1c(-c2ccccn2)nn2c1CCC2.CC(C)OB(OC(C)C)OC(C)C>O1CCCC1>OB(O)c1c(-c2ccccn2)nn2c1CCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c3650d1852364983bc95078ec95f688b | ClI.O=S(=O)(Cl)c1ccccc1.c1cnc2[nH]ccc2c1>>O=S(=O)(c1ccccc1)n1cc(I)c2cccnc21 | C(C)N(CC)CC.C1(=CC=CC=C1)S(=O)(=O)Cl.ICl.N1C=CC2=CC=CN=C12>>C1(=CC=CC=C1)S(=O)(=O)N1C=C(C=2C1=NC=CC2)I | Cl[I:13].Cl[S:2](=[O:1])(=[O:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.[nH:10]1[cH:11][cH:12][c:14]2[cH:15][cH:16][cH:17][n:18][c:19]12>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[n:10]1[cH:11][c:12]([I:13])[c:14]2[cH:15][cH:16][cH:17][n:18][c:19]12 | ClI.O=S(=O)(Cl)c1ccccc1.c1cnc2[nH]ccc2c1 | O=S(=O)(c1ccccc1)n1cc(I)c2cccnc21 | null | CN(C)C=1C=CN=CC1 | N1=CC=CC=C1.C(Cl)Cl.C(C)(=O)OCC | Miscellaneous | OtherReaction | b975ed4cf7a6a8c52b5a60108759572448cd95fb2de559827ec4d69c8a68204d | 51ac21fb371666dad6c719abf761fc77677c24795c2c33a15b0a4d5159f01965 | O=S(=O)(c1ccccc1)n1ccc2cccnc21 | Cl-[I;H0;D1;+0:1].Cl-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7].[c:8]:[c:9]1:[cH;D2;+0:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1:[#7;a:14]:[c:15]>>[I;H0;D1;+0:1]-[c;H0;D3;+0:10]1:[c:11]:[n;H0;D3;+0:12](-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7]):[c:13](:[#7;a:14]:[c:15]):[c:9]:1:[c:8] | 64 | [{"value": 64.0, "product": "C1(=CC=CC=C1)S(=O)(=O)N1C=C(C=2C1=NC=CC2)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.0, "product": "C1(=CC=CC=C1)S(=O)(=O)N1C=C(C=2C1=NC=CC2)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Add a solution of iodine monochloride (0.76 g, 4.7 mmol) in methylene chloride (4 mL) into a solution of 7-azaindole (Aldrich; 0.5 g, 4.2 mmol) in pyridine (4 mL) at 0° C. Stir the reaction at 0° C. for 15 min, then at room temperature for 30 min. Dilute with ethyl acetate and wash the organic phase with 1N aqueous hyd... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Aromatic halide | c1cnc2[nH]ccc2c1 | c1c[nH]c2ncccc12 | c1ccccc1.c1c[nH]c2ncccc12 | HCl | CN(C)C=1C=CN=CC1.N1=CC=CC=C1.C(Cl)Cl.C(C)(=O)OCC | null | 0.5 | ClI.O=S(=O)(Cl)c1ccccc1.c1cnc2[nH]ccc2c1>CN(C)C=1C=CN=CC1.N1=CC=CC=C1.C(Cl)Cl.C(C)(=O)OCC>O=S(=O)(c1ccccc1)n1cc(I)c2cccnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5703788575ec4eb7aea844932a8f0369 | Nc1cc[nH]n1.O=CC(Br)C=O>>Brc1cnc2[nH]ncc2c1 | BrC(C=O)C=O.NC1=NNC=C1>>BrC=1C=C2C(=NC1)NN=C2 | [NH2:4][c:5]1[n:6][nH:7][cH:8][cH:9]1.O=[CH:3][CH:2]([Br:1])[CH:10]=O>>[Br:1][c:2]1[cH:3][n:4][c:5]2[nH:6][n:7][cH:8][c:9]2[cH:10]1 | Nc1cc[nH]n1.O=CC(Br)C=O | Brc1cnc2[nH]ncc2c1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 32738e51f3f20f99e2893cbe6ca323912d37feaf4e65742f859b1117afe577f7 | a93805e04cc8dd14ac1dcf6fd44f35b336dc99c8be7299d44004d554881927e7 | c1cnc2[nH]ncc2c1 | O=[CH;D2;+0:1]-[CH;D3;+0:2](-[Br;D1;H0:3])-[CH;D2;+0:4]=O.[NH2;D1;+0:5]-[c:6]1:[cH;D2;+0:7]:[c:8]:[nH;D2;+0:9]:[n;H0;D2;+0:10]:1>>[Br;D1;H0:3]-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[c;H0;D3;+0:7]2:[c:8]:[n;H0;D2;+0:9]:[nH;D2;+0:10]:[c:6]:2:[n;H0;D2;+0:5]:[cH;D2;+0:4]:1 | 11.2 | [{"value": 11.0, "product": "BrC=1C=C2C(=NC1)NN=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.2, "product": "BrC=1C=C2C(=NC1)NN=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Dissolve 2-bromomalonaldehyde (Aldrich; 2.5 g, 16.5 mmol) and 3-aminopyrazole (Aldrich; 1.38 g, 16.5 mmol) in glacial acetic acid (25 mL) and reflux under nitrogen for 2 h. Concentrate under reduced pressure and dissolve the residue in absolute methanol (150 mL), vacuum filter through a pad of diatomaceous earth and co... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Aldehyde.Primary amine | Aromatic halide | c1cn[nH]c1 | c1cnc2[nH]ncc2c1 | c1cnc2[nH]ncc2c1 | HO- | C(C)(=O)O | null | null | Nc1cc[nH]n1.O=CC(Br)C=O>C(C)(=O)O>Brc1cnc2[nH]ncc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dd53d6932502484faa6025be9add0023 | Nc1ccnn1-c1ccccc1.O=CC(Br)C=O>>Brc1cnc2c(cnn2-c2ccccc2)c1 | C1(=CC=CC=C1)N1N=CC=C1N.BrC(C=O)C=O>>BrC=1C=C2C(=NC1)N(N=C2)C2=CC=CC=C2 | [NH2:4][c:5]1[cH:6][cH:7][n:8][n:9]1-[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.O=[CH:3][CH:2]([Br:1])[CH:16]=O>>[Br:1][c:2]1[cH:3][n:4][c:5]2[c:6]([cH:7][n:8][n:9]2-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16]1 | Nc1ccnn1-c1ccccc1.O=CC(Br)C=O | Brc1cnc2c(cnn2-c2ccccc2)c1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 588d35513d13b7edcdbab1f8b8ebcd6f6f6ab7c0443ebd853e1dc6bd13906ef7 | a93805e04cc8dd14ac1dcf6fd44f35b336dc99c8be7299d44004d554881927e7 | c1ccc(-n2ncc3cccnc32)cc1 | O=[CH;D2;+0:1]-[CH;D3;+0:2](-[Br;D1;H0:3])-[CH;D2;+0:4]=O.[NH2;D1;+0:5]-[c:6]1:[cH;D2;+0:7]:[c:8]:[#7;a:9]:[#7;a:10]:1-[c:11]>>[Br;D1;H0:3]-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[c;H0;D3;+0:7]2:[c:8]:[#7;a:9]:[#7;a:10](-[c:11]):[c:6]:2:[n;H0;D2;+0:5]:[cH;D2;+0:4]:1 | 28.7 | [{"value": 28.0, "product": "BrC=1C=C2C(=NC1)N(N=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.7, "product": "BrC=1C=C2C(=NC1)N(N=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Dissolve 1-phenyl-5-aminopyrazole (Tokyo Kasei Kogyo Co. LTD; 1.5 g, 9.4 mmol) and 2-bromomalonaldehyde (Aldrich; 1.42 g, 9.4 mmol) in glacial acetic acid (170 mL) and reflux under nitrogen for 5 h. Concentrate under reduced pressure and purify via chromatography (silica gel, dichloromethane) to obtain 740 mg (28%) of ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Aldehyde.Primary amine | Aromatic halide | c1cc[nH]n1 | c1cnc2n[nH]cc2c1 | c1cnc2n[nH]cc2c1.c1ccccc1 | HO- | C(C)(=O)O | null | null | Nc1ccnn1-c1ccccc1.O=CC(Br)C=O>C(C)(=O)O>Brc1cnc2c(cnn2-c2ccccc2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-55273c1aa3e34e979796e4e2114b3cbe | Cn1nccc1N.O=CC(Br)C=O>>Cn1ncc2cc(Br)cnc21 | CN1N=CC=C1N.BrC(C=O)C=O>>BrC=1C=C2C(=NC1)N(N=C2)C | [CH3:1][n:2]1[n:3][cH:4][cH:5][c:11]1[NH2:10].O=[CH:6][CH:7]([Br:8])[CH:9]=O>>[CH3:1][n:2]1[n:3][cH:4][c:5]2[cH:6][c:7]([Br:8])[cH:9][n:10][c:11]12 | Cn1nccc1N.O=CC(Br)C=O | Cn1ncc2cc(Br)cnc21 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 32cf2f86e966ebfdc9e59cace89339fad0034c7c378972d27d9631aaa46e163f | a93805e04cc8dd14ac1dcf6fd44f35b336dc99c8be7299d44004d554881927e7 | c1cnc2[nH]ncc2c1 | O=[CH;D2;+0:1]-[CH;D3;+0:2](-[Br;D1;H0:3])-[CH;D2;+0:4]=O.[C;D1;H3:5]-[#7;a:6]1:[#7;a:7]:[c:8]:[cH;D2;+0:9]:[c:10]:1-[NH2;D1;+0:11]>>[Br;D1;H0:3]-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[c;H0;D3;+0:9]2:[c:8]:[#7;a:7]:[#7;a:6](-[C;D1;H3:5]):[c:10]:2:[n;H0;D2;+0:11]:[cH;D2;+0:4]:1 | 27.9 | [{"value": 27.0, "product": "BrC=1C=C2C(=NC1)N(N=C2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.9, "product": "BrC=1C=C2C(=NC1)N(N=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Dissolve 1-methyl-5-aminopyrazole (Butt Park LTD; 1.0 g, 10.3 mmol) and 2-bromomalonaldehyde (Aldrich; 1.55 g, 10.3 mmol) in glacial acetic acid (160 mL) and reflux under nitrogen for 48 h. Concentrate under reduced pressure and purify via chromatography (silica gel, 90% dichloromethane/10% diethyl ether) to obtain 610... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Aldehyde.Primary amine | Aromatic halide | c1ccn[nH]1 | c1cnc2[nH]ncc2c1 | c1cnc2[nH]ncc2c1 | HO- | C(C)(=O)O | null | null | Cn1nccc1N.O=CC(Br)C=O>C(C)(=O)O>Cn1ncc2cc(Br)cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c24db5fb71c547d8affbbcb03f234aa4 | CI.c1ccc(-c2nn3c(c2-c2ccnc4[nH]ccc24)CCC3)nc1>>Cn1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc21 | Cl.[H-].[K+].N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=C1C(=NC=C2)NC=C1.IC>>CN1C=CC=2C1=NC=CC2C2=C1N(N=C2C2=NC=CC=C2)CCC1 | I[CH3:1].[nH:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[c:8](-[c:9]4[cH:10][cH:11][cH:12][cH:13][n:14]4)[n:15][n:16]4[c:17]3[CH2:18][CH2:19][CH2:20]4)[cH:21][cH:22][n:23][c:24]12>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[c:8](-[c:9]4[cH:10][cH:11][cH:12][cH:13][n:14]4)[n:15][n:16]4[c:17]3[CH2:18][CH2:19][CH2:20]4)[cH:21][c... | CI.c1ccc(-c2nn3c(c2-c2ccnc4[nH]ccc24)CCC3)nc1 | Cn1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc21 | null | null | CCCCCC.CN(C=O)C.C(C)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | ae71ae396afb4259a35ac85913acc2369563a445c2808cc31c1dca2e0e80552a | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ccc(-c2nn3c(c2-c2ccnc4[nH]ccc24)CCC3)nc1 | I-[CH3;D1;+0:1].[c:2]:[#7;a:3]:[c:4]1:[c:5]:[c:6]:[c:7]:[nH;D2;+0:8]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:8]1:[c:7]:[c:6]:[c:5]:[c:4]:1:[#7;a:3]:[c:2] | 79.3 | [{"value": 79.0, "product": "CN1C=CC=2C1=NC=CC2C2=C1N(N=C2C2=NC=CC=C2)CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.3, "product": "CN1C=CC=2C1=NC=CC2C2=C1N(N=C2C2=NC=CC=C2)CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Dissolve 4-[2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-1H-pyrrolo[2,3-b]pyridine (Example 1; 0.150 g, 0.50 mmol) in N,N-dimethylformamide (10 ml). Add n-hexane (2 mL) and cool to 0° C. Add potassium hydride (35% suspension in mineral oil, 0.12 g, 1.0 mmol) and stir under nitrogen at 0° C. for 5 min. Ad... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cnc2[nH]ccc2c1 | c1ccnc2[nH]ccc12 | c1ccncc1.c1cc2n(n1)CCC2.c1ccnc2[nH]ccc12 | HI | CCCCCC.CN(C=O)C.C(C)OCC | null | null | CI.c1ccc(-c2nn3c(c2-c2ccnc4[nH]ccc24)CCC3)nc1>CCCCCC.CN(C=O)C.C(C)OCC>Cn1ccc2c(-c3c(-c4ccccn4)nn4c3CCC4)ccnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-85b8133d19774a839e866e15eabf782d | O=S(=O)(c1ccccc1)n1cc(I)c2cccnc21.OB(O)c1c(-c2ccccn2)nn2c1CCC2>>O=S(=O)(c1ccccc1)n1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2cccnc21 | C1(=CC=CC=C1)S(=O)(=O)N1C=C(C=2C1=NC=CC2)I.N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)B(O)O>>C1(=CC=CC=C1)S(=O)(=O)N1C=C(C=2C1=NC=CC2)C2=C1N(N=C2C2=NC=CC=C2)CCC1 | I[c:12]1[cH:11][n:10]([S:2](=[O:1])(=[O:3])[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[c:32]2[c:27]1[cH:28][cH:29][cH:30][n:31]2.OB(O)[c:13]1[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][n:20]2)[n:21][n:22]2[c:23]1[CH2:24][CH2:25][CH2:26]2>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[n:10]1[cH:11][c:12](-[c:13]... | O=S(=O)(c1ccccc1)n1cc(I)c2cccnc21.OB(O)c1c(-c2ccccn2)nn2c1CCC2 | O=S(=O)(c1ccccc1)n1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2cccnc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | f4d23c9df62bf010df4926cb296258d1e99570e02344e49741d8e9526551e283 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1ccccc1)n1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2cccnc21 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3](-[#16:4]):[c:5](:[#7;a:6]:[c:7]):[c:8]:1:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11](-[c:12]:[#7;a:13]):[#7;a:14]:[#7;a:15](:[c:16]:1-[C:17])-[C:18]>>[#16:4]-[#7;a:3]1:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10]2:[c:11](-[c:12]:[#7;a:13]):[#7;a:14]:[#7;a:15](:[c:16]:2-[C:17])-[C:18]):[c:8](:[c:9]):... | null | [] | null | null | null | null | Using Preparation 3A, 1-benzene-sulfonyl-3-iodo-1H-pyrrolo[2,3-b]pyridine (Preparation 5) is reacted with 2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-boronic acid (Preparation 2) to provide the titled product. MS (ES) m/z=442 (M+H).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1c[nH]c2ncccc12.c1cc2n(n1)CCC2 | c1cc2n(n1)CCC2.c1c[nH]c2ncccc12 | c1ccccc1.c1ccncc1.c1cc2n(n1)CCC2.c1c[nH]c2ncccc12 | HI.B | null | null | null | O=S(=O)(c1ccccc1)n1cc(I)c2cccnc21.OB(O)c1c(-c2ccccn2)nn2c1CCC2>>O=S(=O)(c1ccccc1)n1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2cccnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aec83f5b9e184fbb9c7e9c8347447d4c | O=S(=O)(c1ccccc1)n1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2cccnc21>>c1ccc(-c2nn3c(c2-c2c[nH]c4ncccc24)CCC3)nc1 | C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)S(=O)(=O)N1C=C(C=2C1=NC=CC2)C2=C1N(N=C2C2=NC=CC=C2)CCC1>>N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CNC1=NC=CC=C12 | O=S(=O)(c1ccccc1)[n:12]1[cH:11][c:10](-[c:9]2[c:5](-[c:4]3[cH:3][cH:2][cH:1][cH:23][n:22]3)[n:6][n:7]3[c:8]2[CH2:19][CH2:20][CH2:21]3)[c:18]2[c:13]1[n:14][cH:15][cH:16][cH:17]2>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[n:6][n:7]3[c:8]([c:9]2-[c:10]2[cH:11][nH:12][c:13]4[n:14][cH:15][cH:16][cH:17][c:18]24)[CH2:19][CH2:20][CH2:2... | O=S(=O)(c1ccccc1)n1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2cccnc21 | c1ccc(-c2nn3c(c2-c2c[nH]c4ncccc24)CCC3)nc1 | null | null | CO.O | Reduction | OtherReaction | b79b6b13e577ad6352dcacf5bbcedb9423c05433f113b00903a5ab65344382bb | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(-c2nn3c(c2-c2c[nH]c4ncccc24)CCC3)nc1 | O=S(=O)(-[n;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:1:[#7;a:6]:[c:7])-c1:c:c:c:c:c:1>>[c:7]:[#7;a:6]:[c:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | 68 | [{"value": 68.0, "product": "N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CNC1=NC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.9, "product": "N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CNC1=NC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Add potassium carbonate (21 mg, 0.15 mmol) to a solution of 1-benzenesulfonyl-3-[2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-1H-pyrrolo[2,3-b]pyridine (Example 3, Part A; 34 mg, 0.77 mmol) in methanol/water (0.9 mL/0.3 mL). Reflux the reaction overnight (16 h). Concentrate in vacuo, add aqueous sodium c... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1c[nH]c2ncccc12 | c1cnc2[nH]ccc2c1 | c1ccncc1.c1cnc2[nH]ccc2c1.c1cc2n(n1)CCC2 | HO- | CO.O | null | null | O=S(=O)(c1ccccc1)n1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2cccnc21>CO.O>c1ccc(-c2nn3c(c2-c2c[nH]c4ncccc24)CCC3)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f5a33ce93a8f4fcda9ec73b282de5200 | O=S(=O)(c1ccccc1)n1cc(I)c2ccncc21.OB(O)c1c(-c2ccccn2)nn2c1CCC2>>O=S(=O)(c1ccccc1)n1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2ccncc21 | C1(=CC=CC=C1)S(=O)(=O)N1C=C(C=2C1=CN=CC2)I.N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)B(O)O>>C1(=CC=CC=C1)S(=O)(=O)N1C=C(C=2C1=CN=CC2)C2=C1N(N=C2C2=NC=CC=C2)CCC1 | I[c:12]1[cH:11][n:10]([S:2](=[O:1])(=[O:3])[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[c:32]2[c:27]1[cH:28][cH:29][n:30][cH:31]2.OB(O)[c:13]1[c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][n:20]2)[n:21][n:22]2[c:23]1[CH2:24][CH2:25][CH2:26]2>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[n:10]1[cH:11][c:12](-[c:13]... | O=S(=O)(c1ccccc1)n1cc(I)c2ccncc21.OB(O)c1c(-c2ccccn2)nn2c1CCC2 | O=S(=O)(c1ccccc1)n1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2ccncc21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d207c2505c5fb39a11b46149df4a476f60f948af996d535ab0e1604410265e85 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1ccccc1)n1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2ccncc21 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3](-[#16:4]):[c:5]2:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:1.O-B(-O)-[c;H0;D3;+0:11]1:[c:12](-[c:13]:[#7;a:14]):[#7;a:15]:[#7;a:16](:[c:17]:1-[C:18])-[C:19]>>[#16:4]-[#7;a:3]1:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:11]2:[c:12](-[c:13]:[#7;a:14]):[#7;a:15]:[#7;a:16](:[c:17]:2-[C:18])-[C:19]):[c:10]... | null | [] | null | null | null | null | Using Preparation 3A, 1-benzenesulfonyl-3-iodo-1H-pyrrolo[2,3-c]pyridine (Preparation 8) is reacted with 2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-boronic acid (Preparation 2) to provide the titled product. MS (ES) m/z=442 (M+H).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1c[nH]c2cnccc12.c1cc2n(n1)CCC2 | c1cc2n(n1)CCC2.c1c[nH]c2cnccc12 | c1ccccc1.c1ccncc1.c1cc2n(n1)CCC2.c1c[nH]c2cnccc12 | HI.B | null | null | null | O=S(=O)(c1ccccc1)n1cc(I)c2ccncc21.OB(O)c1c(-c2ccccn2)nn2c1CCC2>>O=S(=O)(c1ccccc1)n1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2ccncc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b1b9ab84b54c47719578b7db7263db69 | O=S(=O)(c1ccccc1)n1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2ccncc21>>c1ccc(-c2nn3c(c2-c2c[nH]c4cnccc24)CCC3)nc1 | C([O-])([O-])=O.[K+].[K+].C1(=CC=CC=C1)S(=O)(=O)N1C=C(C=2C1=CN=CC2)C2=C1N(N=C2C2=NC=CC=C2)CCC1>>N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CNC1=CN=CC=C12 | O=S(=O)(c1ccccc1)[n:12]1[cH:11][c:10](-[c:9]2[c:5](-[c:4]3[cH:3][cH:2][cH:1][cH:23][n:22]3)[n:6][n:7]3[c:8]2[CH2:19][CH2:20][CH2:21]3)[c:18]2[c:13]1[cH:14][n:15][cH:16][cH:17]2>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[n:6][n:7]3[c:8]([c:9]2-[c:10]2[cH:11][nH:12][c:13]4[cH:14][n:15][cH:16][cH:17][c:18]24)[CH2:19][CH2:20][CH2:2... | O=S(=O)(c1ccccc1)n1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2ccncc21 | c1ccc(-c2nn3c(c2-c2c[nH]c4cnccc24)CCC3)nc1 | null | null | CO | Reduction | OtherReaction | 06293e793e0ea2e04051e7a91cf49b2f0688fde2b400f136456dfbecefae1f03 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(-c2nn3c(c2-c2c[nH]c4cnccc24)CCC3)nc1 | O=S(=O)(-[n;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:1:[c:6]:[#7;a:7]:[c:8])-c1:c:c:c:c:c:1>>[c:8]:[#7;a:7]:[c:6]:[c:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | 64.5 | [{"value": 64.0, "product": "N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CNC1=CN=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.5, "product": "N1=C(C=CC=C1)C=1C(=C2N(N1)CCC2)C2=CNC1=CN=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Add potassium carbonate (40 mg, 0.29 mmol) to a solution of 1-benzenesulfonyl-3-[2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-1H-pyrrolo[2,3-c]pyridine (Example 12, Part A; 16 mg, 0.036 mmol) in methanol (3 mL). Reflux the reaction mixture overnight (15 h). Concentrate the mixture in vacuo and purify by ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.c1c[nH]c2cnccc12 | c1cc2cc[nH]c2cn1 | c1ccncc1.c1cc2cc[nH]c2cn1.c1cc2n(n1)CCC2 | HO- | CO | null | null | O=S(=O)(c1ccccc1)n1cc(-c2c(-c3ccccn3)nn3c2CCC3)c2ccncc21>CO>c1ccc(-c2nn3c(c2-c2c[nH]c4cnccc24)CCC3)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-06b8962ae50e4e5fbb92e945f1106796 | O=C(Cl)C(=O)Cl.O=c1[nH]ccc2cccnc12>>Oc1nccc2ccc(Cl)nc12 | ClC1=CC(=CC=C1)C(=O)OO.C(C(=O)Cl)(=O)Cl.N1=CC=CC=2C=CNC(C12)=O>>ClC1=NC2=C(N=CC=C2C=C1)O | O=C(Cl)C(=O)[Cl:10].[O:1]=[c:2]1[nH:3][cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][n:11][c:12]12>>[OH:1][c:2]1[n:3][cH:4][cH:5][c:6]2[cH:7][cH:8][c:9]([Cl:10])[n:11][c:12]12 | O=C(Cl)C(=O)Cl.O=c1[nH]ccc2cccnc12 | Oc1nccc2ccc(Cl)nc12 | null | null | C(Cl)(Cl)Cl.CN(C=O)C | Functional Group Interconversion | OtherReaction | 1302ae76d6943833acfaba54330de76ac8e57dd44a677c26b341b5f8c8122622 | a6e46b9deb61fda6f88f40dc8ef4943b48440699c25353ef876d3cd2a93c0fee | c1cnc2cnccc2c1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].[O;H0;D1;+0:2]=[c;H0;D3;+0:3]1:[nH;D2;+0:4]:[c:5]:[c:6]:[c:7]2:[c:8]:[c:9]:[cH;D2;+0:10]:[#7;a:11]:[c:12]:2:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:10]1:[#7;a:11]:[c:12]2:[c:7](:[c:6]:[c:5]:[n;H0;D2;+0:4]:[c;H0;D3;+0:3]:2-[OH;D1;+0:2]):[c:8]:[c:9]:1 | null | [] | null | null | 30 | MINUTE | In accordance with Scheme 3, the compound of formula X, 1-oxy-7H-[1,7]naphthyridin-8-one can be prepared as follows: The compound of formula IX, 7H-[1,7]naphthyridin-8-one (which can be prepared from commercially available starting product in accordance with literature Chemical & Pharmaceutical Bullentin (1985), 33(2),... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide | Aromatic halide.Aromatic alcohol | c1nccc2cccnc12 | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | HCl | C(Cl)(Cl)Cl.CN(C=O)C | null | 0.5 | O=C(Cl)C(=O)Cl.O=c1[nH]ccc2cccnc12>C(Cl)(Cl)Cl.CN(C=O)C>Oc1nccc2ccc(Cl)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5937f0fba58341699293691ccde86743 | Cc1cccc(N)n1.Clc1nccc2cccnc12>>Cc1cccc(Nc2nccc3cccnc23)n1 | ClC=1N=CC=C2C=CC=NC12.NC1=NC(=CC=C1)C.C1(=CC=CC=C1)P(C1=CC=CC=2C(C3=CC=CC(=C3OC12)P(C1=CC=CC=C1)C1=CC=CC=C1)(C)C)C1=CC=CC=C1.C([O-])([O-])=O.[Cs+].[Cs+]>>CC1=CC=CC(=N1)NC=1N=CC=C2C=CC=NC12 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[n:18]1.Cl[c:8]1[n:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][n:16][c:17]12>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][c:12]3[cH:13][cH:14][cH:15][n:16][c:17]23)[n:18]1 | Cc1cccc(N)n1.Clc1nccc2cccnc12 | Cc1cccc(Nc2nccc3cccnc23)n1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 9aaceba939b33cad498c676d532db91be3635aea14c5a94e898ffbf17b5632f1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc3cccnc23)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]):[c:4](:[c:5]):[#7;a:6]:[c:7] | 34 | [{"value": 34.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 50 | MINUTE | 8-Chloro-[1,7]naphthyridine (Example A) (0.2 g, 1.2 mmol) and 2-amino-6-methylpyridine (0.13 g, 1.2 mmol) were dissolved in 8 ml dry dioxane. 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (145 mg, 0.24 mmol), cesium carbonate (0.63 g, 1.95 mmol) and tri(dibenzylideneacetone)dipalladium chloroform complex (0.13 g, 0.1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1ccncc1.c1cnc2cnccc2c1 | HCl | O1CCOCC1 | 150 | 0.833333 | Cc1cccc(N)n1.Clc1nccc2cccnc12>O1CCOCC1>Cc1cccc(Nc2nccc3cccnc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5bbf134c408f4de982eab3a1043e9241 | Clc1nccc2cccnc12.Nc1cccc(Cl)c1>>Clc1cccc(Nc2nccc3cccnc23)c1 | ClC=1N=CC=C2C=CC=NC12.ClC=1C=C(N)C=CC1>>ClC=1C=C(C=CC1)NC=1N=CC=C2C=CC=NC12 | Cl[c:8]1[n:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][n:16][c:17]12.[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[cH:18]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][cH:11][c:12]3[cH:13][cH:14][cH:15][n:16][c:17]23)[cH:18]1 | Clc1nccc2cccnc12.Nc1cccc(Cl)c1 | Clc1cccc(Nc2nccc3cccnc23)c1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 9aaceba939b33cad498c676d532db91be3635aea14c5a94e898ffbf17b5632f1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc3cccnc23)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:4](:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | null | null | The title compound, MS: m/e=256.0 (M+H+), was prepared in accordance with the general method of example 1 from 8-chloro-[1,7]naphthyridine and 3-chloroaniline.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1ccccc1.c1cnc2cnccc2c1 | HCl | null | null | null | Clc1nccc2cccnc12.Nc1cccc(Cl)c1>>Clc1cccc(Nc2nccc3cccnc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1467d2b8ac21406eb7f657c5285b5d8b | Clc1nccc2cccnc12.Nc1ccc(F)cn1>>Fc1ccc(Nc2nccc3cccnc23)nc1 | ClC=1N=CC=C2C=CC=NC12.NC1=NC=C(C=C1)F>>FC=1C=CC(=NC1)NC=1N=CC=C2C=CC=NC12 | Cl[c:7]1[n:8][cH:9][cH:10][c:11]2[cH:12][cH:13][cH:14][n:15][c:16]12.[F:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[n:17][cH:18]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][cH:10][c:11]3[cH:12][cH:13][cH:14][n:15][c:16]23)[n:17][cH:18]1 | Clc1nccc2cccnc12.Nc1ccc(F)cn1 | Fc1ccc(Nc2nccc3cccnc23)nc1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 9aaceba939b33cad498c676d532db91be3635aea14c5a94e898ffbf17b5632f1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc3cccnc23)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[c:5]:[c:4](:[#7;a:6]:[c:7]):[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | The title compound, MS: m/e=241.2 (M+H+), was prepared in accordance with the general method of example 1 from 8-chloro-[1,7]naphthyridine and 2-amino-5-fluoropyridine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1ccncc1.c1cnc2cnccc2c1 | HCl | null | null | null | Clc1nccc2cccnc12.Nc1ccc(F)cn1>>Fc1ccc(Nc2nccc3cccnc23)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-37c38bbc1f14453dbe62a6868d9020ab | Cc1csc(N)n1.Clc1nccc2cccnc12>>Cc1csc(Nc2nccc3cccnc23)n1 | ClC=1N=CC=C2C=CC=NC12.NC=1SC=C(N1)C>>CC=1N=C(SC1)NC=1N=CC=C2C=CC=NC12 | [CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:17]1.Cl[c:7]1[n:8][cH:9][cH:10][c:11]2[cH:12][cH:13][cH:14][n:15][c:16]12>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][cH:10][c:11]3[cH:12][cH:13][cH:14][n:15][c:16]23)[n:17]1 | Cc1csc(N)n1.Clc1nccc2cccnc12 | Cc1csc(Nc2nccc3cccnc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 9aaceba939b33cad498c676d532db91be3635aea14c5a94e898ffbf17b5632f1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cnc2c(Nc3nccs3)nccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[NH2;D1;+0:8]-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1>>[c:5]:[c:4](:[#7;a:6]:[c:7]):[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1):[#7;a:2]:[c:3] | null | [] | null | null | null | null | The title compound, MS: m/e=243.3 (M+H+), was prepared in accordance with the general method of example 1 from 8-chloro-[1,7]naphthyridine and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1cscn1.c1cnc2cnccc2c1 | HCl | null | null | null | Cc1csc(N)n1.Clc1nccc2cccnc12>>Cc1csc(Nc2nccc3cccnc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae19bdf49439425988639b55855b1245 | Cc1cccc(Br)n1.Nc1ncc(-c2cccnc2)c2cccnc12>>Cc1cccc(Nc2ncc(-c3cccnc3)c3cccnc23)n1 | N1=CC(=CC=C1)C1=C2C=CC=NC2=C(N=C1)N.BrC1=NC(=CC=C1)C.C1(=CC=CC=C1)P(C1=CC=CC=2C(C3=CC=CC(=C3OC12)P(C1=CC=CC=C1)C1=CC=CC=C1)(C)C)C1=CC=CC=C1.C([O-])([O-])=O.[Cs+].[Cs+]>>CC1=CC=CC(=N1)NC=1N=CC(=C2C=CC=NC12)C=1C=NC=CC1 | Br[c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[n:24]1.[NH2:7][c:8]1[n:9][cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][n:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][n:22][c:23]12>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][n:16][cH:17]3)[c:18]3[cH:19][cH:20][cH:21][n:22][c:23]... | Cc1cccc(Br)n1.Nc1ncc(-c2cccnc2)c2cccnc12 | Cc1cccc(Nc2ncc(-c3cccnc3)c3cccnc23)n1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncc(-c3cccnc3)c3cccnc23)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](:[c:11]):[#7;a:12]:[c:13]>>[c:9]:[#7;a:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:10](:[c:11]):[#7;a:12]:[c:13] | 47 | [{"value": 47.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 20 | HOUR | 5-Pyridin-3-yl-[1,7]naphthyridin-8-ylamine (0.1 g, 0.45 mmol) and 2-bromo-6-methylpyridine (0.14 g, 0.8 mmol) were dissolved in 4 ml dry dioxane. 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (52 mg, 0.09 mmol), cesium carbonate (0.23 g, 0.72 mmol) and tri(dibenzylideneacetone)dipalladium chloroform complex (47 mg, 0... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccncc1.c1cnc2cnccc2c1 | HBr | O1CCOCC1 | 130 | 20 | Cc1cccc(Br)n1.Nc1ncc(-c2cccnc2)c2cccnc12>O1CCOCC1>Cc1cccc(Nc2ncc(-c3cccnc3)c3cccnc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e9ec4d1b82f5417492b9f25972dda543 | Clc1cccc(I)c1.Nc1ncc(-c2cccnc2)c2cccnc12>>Clc1cccc(Nc2ncc(-c3cccnc3)c3cccnc23)c1 | N1=CC(=CC=C1)C1=C2C=CC=NC2=C(N=C1)N.ClC1=CC(=CC=C1)I>>ClC=1C=C(C=CC1)NC=1N=CC(=C2C=CC=NC12)C=1C=NC=CC1 | I[c:6]1[cH:5][cH:4][cH:3][c:2]([Cl:1])[cH:24]1.[NH2:7][c:8]1[n:9][cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][n:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][n:22][c:23]12>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][n:16][cH:17]3)[c:18]3[cH:19][cH:20][cH:21][n:22][c:23]23... | Clc1cccc(I)c1.Nc1ncc(-c2cccnc2)c2cccnc12 | Clc1cccc(Nc2ncc(-c3cccnc3)c3cccnc23)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncc(-c3cccnc3)c3cccnc23)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](:[c:11]):[#7;a:12]:[c:13]>>[c:9]:[#7;a:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:10](:[c:11]):[#7;a:12]:[c:13] | null | [] | null | null | null | null | The title compound, MS: m/e=333.1 (M+H+), was prepared in accordance with the general method of example 6 step 3 from 5-pyridin-3-yl-[1,7]naphthyridin-8-ylamine and 1-chloro-3-iodobenzene.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1.c1cnc2cnccc2c1 | HI | null | null | null | Clc1cccc(I)c1.Nc1ncc(-c2cccnc2)c2cccnc12>>Clc1cccc(Nc2ncc(-c3cccnc3)c3cccnc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef62fafdc40e4c7f8b05de338f7534ca | Clc1cc(I)ccn1.Nc1ncc(-c2cccnc2)c2cccnc12>>Clc1cc(Nc2ncc(-c3cccnc3)c3cccnc23)ccn1 | N1=CC(=CC=C1)C1=C2C=CC=NC2=C(N=C1)N.ClC1=NC=CC(=C1)I>>ClC1=NC=CC(=C1)NC=1N=CC(=C2C=CC=NC12)C=1C=NC=CC1 | I[c:4]1[cH:3][c:2]([Cl:1])[n:24][cH:23][cH:22]1.[NH2:5][c:6]1[n:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][n:14][cH:15]2)[c:16]2[cH:17][cH:18][cH:19][n:20][c:21]12>>[Cl:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][cH:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][n:14][cH:15]3)[c:16]3[cH:17][cH:18][cH:19][n:20][c:21]23)[cH:22][cH:23]... | Clc1cc(I)ccn1.Nc1ncc(-c2cccnc2)c2cccnc12 | Clc1cc(Nc2ncc(-c3cccnc3)c3cccnc23)ccn1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncc(-c2cnc(Nc3ccncc3)c3ncccc23)c1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1.[NH2;D1;+0:8]-[c:9](:[#7;a:10]:[c:11]):[c:12](:[c:13]):[#7;a:14]:[c:15]>>[Cl;D1;H0:6]-[c:5]1:[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[#7;a:10]:[c:11]):[c:12](:[c:13]):[#7;a:14]:[c:15]):[c:7]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=334.2 (M+H+), was prepared in accordance with the general method of example 6 step 3 from 5-pyridin-3-yl-[1,7]naphthyridin-8-ylamine and 2-chloro-4-iodopyridine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccncc1.c1cnc2cnccc2c1 | HI | null | null | null | Clc1cc(I)ccn1.Nc1ncc(-c2cccnc2)c2cccnc12>>Clc1cc(Nc2ncc(-c3cccnc3)c3cccnc23)ccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-85cac396e4e94f9086f5e652b8e1564b | Cc1ccc(Br)nc1.Nc1ncc(-c2cccnc2)c2cccnc12>>Cc1ccc(Nc2ncc(-c3cccnc3)c3cccnc23)nc1 | N1=CC(=CC=C1)C1=C2C=CC=NC2=C(N=C1)N.BrC1=NC=C(C=C1)C>>CC=1C=CC(=NC1)NC=1N=CC(=C2C=CC=NC12)C=1C=NC=CC1 | Br[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:24][n:23]1.[NH2:6][c:7]1[n:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][n:21][c:22]12>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][n:15][cH:16]3)[c:17]3[cH:18][cH:19][cH:20][n:21][c:22]23)[n:2... | Cc1ccc(Br)nc1.Nc1ncc(-c2cccnc2)c2cccnc12 | Cc1ccc(Nc2ncc(-c3cccnc3)c3cccnc23)nc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncc(-c3cccnc3)c3cccnc23)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](:[c:11]):[#7;a:12]:[c:13]>>[c:11]:[c:10](:[#7;a:12]:[c:13]):[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:8]:[c:9] | null | [] | null | null | null | null | The title compound, MS: m/e=314.0 (M+H+), was prepared in accordance with the general method of example 6 step 3 from 5-pyridin-3-yl-[1,7]naphthyridin-8-ylamine and 2-bromo-5-methylpyridine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccncc1.c1cnc2cnccc2c1 | HBr | null | null | null | Cc1ccc(Br)nc1.Nc1ncc(-c2cccnc2)c2cccnc12>>Cc1ccc(Nc2ncc(-c3cccnc3)c3cccnc23)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-324df7cd464e42a6a2641a47a4b943fb | Fc1ccc(Br)nc1.Nc1ncc(-c2cccnc2)c2cccnc12>>Fc1ccc(Nc2ncc(-c3cccnc3)c3cccnc23)nc1 | N1=CC(=CC=C1)C1=C2C=CC=NC2=C(N=C1)N.BrC1=NC=C(C=C1)F>>FC=1C=CC(=NC1)NC=1N=CC(=C2C=CC=NC12)C=1C=NC=CC1 | Br[c:5]1[cH:4][cH:3][c:2]([F:1])[cH:24][n:23]1.[NH2:6][c:7]1[n:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][n:21][c:22]12>>[F:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][n:15][cH:16]3)[c:17]3[cH:18][cH:19][cH:20][n:21][c:22]23)[n:23][c... | Fc1ccc(Br)nc1.Nc1ncc(-c2cccnc2)c2cccnc12 | Fc1ccc(Nc2ncc(-c3cccnc3)c3cccnc23)nc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncc(-c3cccnc3)c3cccnc23)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](:[c:11]):[#7;a:12]:[c:13]>>[c:11]:[c:10](:[#7;a:12]:[c:13]):[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:8]:[c:9] | null | [] | null | null | null | null | The title compound, MS: m/e=318.1 (M+H+), was prepared in accordance with the general method of example 6 step 3 from 5-pyridin-3-yl-[1,7]naphthyridin-8-ylamine and 2-bromo-5-fluoro-pyridine (Example C).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccncc1.c1cnc2cnccc2c1 | HBr | null | null | null | Fc1ccc(Br)nc1.Nc1ncc(-c2cccnc2)c2cccnc12>>Fc1ccc(Nc2ncc(-c3cccnc3)c3cccnc23)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-33d16f82fb564435b4fa14d04e61ec2a | Fc1ccc(Br)nc1.Nc1ncc(-c2cncc(F)c2)c2cccnc12>>Fc1ccc(Nc2ncc(-c3cncc(F)c3)c3cccnc23)nc1 | FC=1C=C(C=NC1)C1=C2C=CC=NC2=C(N=C1)N.BrC1=NC=C(C=C1)F.C1(=CC=CC=C1)P(C1=CC=CC=2C(C3=CC=CC(=C3OC12)P(C1=CC=CC=C1)C1=CC=CC=C1)(C)C)C1=CC=CC=C1.C([O-])([O-])=O.[Cs+].[Cs+]>>FC=1C=CC(=NC1)NC=1N=CC(=C2C=CC=NC12)C=1C=NC=C(C1)F | Br[c:5]1[cH:4][cH:3][c:2]([F:1])[cH:25][n:24]1.[NH2:6][c:7]1[n:8][cH:9][c:10](-[c:11]2[cH:12][n:13][cH:14][c:15]([F:16])[cH:17]2)[c:18]2[cH:19][cH:20][cH:21][n:22][c:23]12>>[F:1][c:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][n:13][cH:14][c:15]([F:16])[cH:17]3)[c:18]3[cH:19][cH:20][cH:21][n:22][c:... | Fc1ccc(Br)nc1.Nc1ncc(-c2cncc(F)c2)c2cccnc12 | Fc1ccc(Nc2ncc(-c3cncc(F)c3)c3cccnc23)nc1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncc(-c3cccnc3)c3cccnc23)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](:[c:11]):[#7;a:12]:[c:13]>>[c:11]:[c:10](:[#7;a:12]:[c:13]):[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[#7;a:8]:[c:9] | 25 | [{"value": 25.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 20 | HOUR | 5-(5-Fluoro-pyridin-3-yl)-[1,7]naphthyridin-8-ylamine (0.1 g, 0.42 mmol) and 2-bromo-5-fluoropyridine (0.13 g, 0.76 mmol) (Example C) were dissolved in 3 ml dry dioxane. 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (48 mg, 0.084 mmol), cesium carbonate (0.22 g, 0.67 mmol) and tri(dibenzylideneacetone)dipalladium chl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccncc1.c1cnc2cnccc2c1 | HBr | O1CCOCC1 | 130 | 20 | Fc1ccc(Br)nc1.Nc1ncc(-c2cncc(F)c2)c2cccnc12>O1CCOCC1>Fc1ccc(Nc2ncc(-c3cncc(F)c3)c3cccnc23)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-18a9897268bd4a6ab6f168318dcee386 | Clc1ccc(Br)nc1.Nc1ncc(-c2cncc(F)c2)c2cccnc12>>Fc1cncc(-c2cnc(Nc3ccc(Cl)cn3)c3ncccc23)c1 | FC=1C=C(C=NC1)C1=C2C=CC=NC2=C(N=C1)N.BrC1=NC=C(C=C1)Cl>>ClC=1C=CC(=NC1)NC=1N=CC(=C2C=CC=NC12)C=1C=NC=C(C1)F | Br[c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][n:18]1.[F:1][c:2]1[cH:3][n:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]([NH2:11])[c:19]3[n:20][cH:21][cH:22][cH:23][c:24]23)[cH:25]1>>[F:1][c:2]1[cH:3][n:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([Cl:16])[cH:17][n:18]3)[c:19]3[n:20][cH:21][cH:22][c... | Clc1ccc(Br)nc1.Nc1ncc(-c2cncc(F)c2)c2cccnc12 | Fc1cncc(-c2cnc(Nc3ccc(Cl)cn3)c3ncccc23)c1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ncc(-c3cccnc3)c3cccnc23)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](:[c:11]):[#7;a:12]:[c:13]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[#7;a:8]:[c:9]):[c:10](:[c:11]):[#7;a:12]:[c:13]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | The title compound, MS: m/e=352.1 (M+H+), was prepared in accordance with the general method of example 15 step 3 from 5-(5-fluoro-pyridin-3-yl)-[1,7]naphthyridin-8-ylamine and 2-bromo-5-chloropyridine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccncc1.c1cnc2cnccc2c1 | HBr | null | null | null | Clc1ccc(Br)nc1.Nc1ncc(-c2cncc(F)c2)c2cccnc12>>Fc1cncc(-c2cnc(Nc3ccc(Cl)cn3)c3ncccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee25d65f03d5475cb74b9d5915ef83c5 | Cc1ccc2ccnc(Cl)c2n1.Cc1csc(N)n1>>Cc1csc(Nc2nccc3ccc(C)nc23)n1 | ClC=1N=CC=C2C=CC(=NC12)C.NC=1SC=C(N1)C>>CC1=NC2=C(N=CC=C2C=C1)NC=1SC=C(N1)C | Cl[c:7]1[n:8][cH:9][cH:10][c:11]2[cH:12][cH:13][c:14]([CH3:15])[n:16][c:17]12.[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:18]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][cH:10][c:11]3[cH:12][cH:13][c:14]([CH3:15])[n:16][c:17]23)[n:18]1 | Cc1ccc2ccnc(Cl)c2n1.Cc1csc(N)n1 | Cc1csc(Nc2nccc3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 9aaceba939b33cad498c676d532db91be3635aea14c5a94e898ffbf17b5632f1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cnc2c(Nc3nccs3)nccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[NH2;D1;+0:8]-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1>>[c:5]:[c:4](:[#7;a:6]:[c:7]):[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1):[#7;a:2]:[c:3] | null | [] | null | null | null | null | The title compound, MS: m/e=257.2 (M+H+), was prepared in accordance with the general method of example 1 from 8-chloro-2-methyl-[1,7]naphthyridine (Example E) and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1cscn1.c1cnc2cnccc2c1 | HCl | null | null | null | Cc1ccc2ccnc(Cl)c2n1.Cc1csc(N)n1>>Cc1csc(Nc2nccc3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bbd668156b2645fb9ff12d4b73e59082 | Cc1ccc2ccnc(Cl)c2n1.Nc1ccc(Cl)cn1>>Cc1ccc2ccnc(Nc3ccc(Cl)cn3)c2n1 | ClC=1N=CC=C2C=CC(=NC12)C.NC1=NC=C(C=C1)Cl>>ClC=1C=CC(=NC1)NC=1N=CC=C2C=CC(=NC12)C | Cl[c:9]1[n:8][cH:7][cH:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:19][c:18]21.[NH2:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][n:17]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][n:17]3)[c:18]2[n:19]1 | Cc1ccc2ccnc(Cl)c2n1.Nc1ccc(Cl)cn1 | Cc1ccc2ccnc(Nc3ccc(Cl)cn3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 9aaceba939b33cad498c676d532db91be3635aea14c5a94e898ffbf17b5632f1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc3cccnc23)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[c:10]:[c:9](-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]):[#7;a:11]:[c:12] | null | [] | null | null | null | null | The title compound, MS: m/e=271.3 (M+H+), was prepared in accordance with the general method of example 1 from 8-chloro-2-methyl-[1,7]naphthyridine (Example E) and 2-amino-5-chloropyridine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1cnc2cnccc2c1.c1ccncc1 | HCl | null | null | null | Cc1ccc2ccnc(Cl)c2n1.Nc1ccc(Cl)cn1>>Cc1ccc2ccnc(Nc3ccc(Cl)cn3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f3d4c0c1d8ae449d87cc74af3b913da1 | Cc1ccc2ccnc(Cl)c2n1.Nc1ccc(F)cn1>>Cc1ccc2ccnc(Nc3ccc(F)cn3)c2n1 | ClC=1N=CC=C2C=CC(=NC12)C.NC1=NC=C(C=C1)F>>FC=1C=CC(=NC1)NC=1N=CC=C2C=CC(=NC12)C | Cl[c:9]1[n:8][cH:7][cH:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:19][c:18]21.[NH2:10][c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][n:17]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]([F:15])[cH:16][n:17]3)[c:18]2[n:19]1 | Cc1ccc2ccnc(Cl)c2n1.Nc1ccc(F)cn1 | Cc1ccc2ccnc(Nc3ccc(F)cn3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 9aaceba939b33cad498c676d532db91be3635aea14c5a94e898ffbf17b5632f1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc3cccnc23)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[c:10]:[c:9](-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]):[#7;a:11]:[c:12] | null | [] | null | null | null | null | The title compound, MS: m/e=255.3 (M+H+), was prepared in accordance with the general method of example 1 from 8-chloro-2-methyl-[1,7]naphthyridine (Example E) and 2-amino-5-fluoropyridine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1cnc2cnccc2c1.c1ccncc1 | HCl | null | null | null | Cc1ccc2ccnc(Cl)c2n1.Nc1ccc(F)cn1>>Cc1ccc2ccnc(Nc3ccc(F)cn3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a8d13e19f784dc2a430598257aef855 | Cc1ccc2ccnc(Cl)c2n1.Nc1ccnc(Cl)c1>>Cc1ccc2ccnc(Nc3ccnc(Cl)c3)c2n1 | ClC=1N=CC=C2C=CC(=NC12)C.ClC1=NC=CC(=C1)N>>ClC1=NC=CC(=C1)NC=1N=CC=C2C=CC(=NC12)C | Cl[c:9]1[n:8][cH:7][cH:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:19][c:18]21.[NH2:10][c:11]1[cH:12][cH:13][n:14][c:15]([Cl:16])[cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][n:14][c:15]([Cl:16])[cH:17]3)[c:18]2[n:19]1 | Cc1ccc2ccnc(Cl)c2n1.Nc1ccnc(Cl)c1 | Cc1ccc2ccnc(Nc3ccnc(Cl)c3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 9aaceba939b33cad498c676d532db91be3635aea14c5a94e898ffbf17b5632f1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cnc2c(Nc3ccncc3)nccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[NH2;D1;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[c:7]:[#7;a:6]:[c:4](:[c:5]):[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1):[#7;a:2]:[c:3] | null | [] | null | null | null | null | The title compound, MS: m/e=271.2 (M+H+), was prepared in accordance with the general method of example 1 from 8-chloro-2-methyl-[1,7]naphthyridine (Example E) and 2-chloro-4-aminopyridine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1cnc2cnccc2c1.c1ccncc1 | HCl | null | null | null | Cc1ccc2ccnc(Cl)c2n1.Nc1ccnc(Cl)c1>>Cc1ccc2ccnc(Nc3ccnc(Cl)c3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-05997952be354d5190b6cd5cff4ad150 | Cc1ccc2ccnc(Cl)c2n1.Nc1cccc(Cl)c1>>Cc1ccc2ccnc(Nc3cccc(Cl)c3)c2n1 | ClC=1N=CC=C2C=CC(=NC12)C.ClC=1C=C(N)C=CC1>>ClC=1C=C(C=CC1)NC=1N=CC=C2C=CC(=NC12)C | Cl[c:9]1[n:8][cH:7][cH:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:19][c:18]21.[NH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]3)[c:18]2[n:19]1 | Cc1ccc2ccnc(Cl)c2n1.Nc1cccc(Cl)c1 | Cc1ccc2ccnc(Nc3cccc(Cl)c3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 9aaceba939b33cad498c676d532db91be3635aea14c5a94e898ffbf17b5632f1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc3cccnc23)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[c:10]:[c:9](-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]):[c:11] | null | [] | null | null | null | null | The title compound, MS: m/e=270.3/272.2 (M+H+), was prepared in accordance with the general method of example 1 from 8-chloro-2-methyl-[1,7]naphthyridine (Example E) and 3-chloroaniline.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1cnc2cnccc2c1.c1ccccc1 | HCl | null | null | null | Cc1ccc2ccnc(Cl)c2n1.Nc1cccc(Cl)c1>>Cc1ccc2ccnc(Nc3cccc(Cl)c3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f633ee4799454ad18ca22b3f5fdb2bc8 | Cc1ccc2ccnc(Cl)c2n1.Cn1ccc(N)n1>>Cc1ccc2ccnc(Nc3ccn(C)n3)c2n1 | ClC=1N=CC=C2C=CC(=NC12)C.CN1N=C(C=C1)N>>CC1=NC2=C(N=CC=C2C=C1)NC1=NN(C=C1)C | Cl[c:9]1[n:8][cH:7][cH:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:18][c:17]21.[NH2:10][c:11]1[cH:12][cH:13][n:14]([CH3:15])[n:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][n:14]([CH3:15])[n:16]3)[c:17]2[n:18]1 | Cc1ccc2ccnc(Cl)c2n1.Cn1ccc(N)n1 | Cc1ccc2ccnc(Nc3ccn(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 9aaceba939b33cad498c676d532db91be3635aea14c5a94e898ffbf17b5632f1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cnc2c(Nc3cc[nH]n3)nccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[C;D1;H3:8]-[#7;a:9]1:[#7;a:10]:[c:11](-[NH2;D1;+0:12]):[c:13]:[c:14]:1>>[C;D1;H3:8]-[#7;a:9]1:[#7;a:10]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]):[c:13]:[c:14]:1 | null | [] | null | null | null | null | The title compound, MS: m/e=240.3 (M+H+), was prepared in accordance with the general method of example 1 from 8-chloro-2-methyl-[1,7]naphthyridine (Example E) and 1-methyl-1H-pyrazol-3-ylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1cnc2cnccc2c1.c1cc[nH]n1 | HCl | null | null | null | Cc1ccc2ccnc(Cl)c2n1.Cn1ccc(N)n1>>Cc1ccc2ccnc(Nc3ccn(C)n3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ed477f8a60747ec93439a256352e767 | Cc1ccc2ccnc(Cl)c2n1.Cc1nc(N)cs1>>Cc1ccc2ccnc(Nc3csc(C)n3)c2n1 | ClC=1N=CC=C2C=CC(=NC12)C.NC=1N=C(SC1)C>>CC1=NC2=C(N=CC=C2C=C1)NC=1N=C(SC1)C | Cl[c:9]1[n:8][cH:7][cH:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:18][c:17]21.[NH2:10][c:11]1[cH:12][s:13][c:14]([CH3:15])[n:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][s:13][c:14]([CH3:15])[n:16]3)[c:17]2[n:18]1 | Cc1ccc2ccnc(Cl)c2n1.Cc1nc(N)cs1 | Cc1ccc2ccnc(Nc3csc(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 9aaceba939b33cad498c676d532db91be3635aea14c5a94e898ffbf17b5632f1 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cnc2c(Nc3cscn3)nccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[NH2;D1;+0:8]-[c:9]1:[#7;a:10]:[c:11]:[#16;a:12]:[c:13]:1>>[c:7]:[#7;a:6]:[c:4](:[c:5]):[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9]1:[#7;a:10]:[c:11]:[#16;a:12]:[c:13]:1):[#7;a:2]:[c:3] | null | [] | null | null | null | null | The title compound, MS: m/e=257.2 (M+H+), was prepared in accordance with the general method of example 1 from 8-chloro-2-methyl-[1,7]naphthyridine (Example E) and 4-amino-2-methylthiazole (Example F).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1cnc2cnccc2c1.c1cscn1 | HCl | null | null | null | Cc1ccc2ccnc(Cl)c2n1.Cc1nc(N)cs1>>Cc1ccc2ccnc(Nc3csc(C)n3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb5254cd0daa47f9b18dffbad37835dc | Cc1csc(N)n1.O=S(=O)(Oc1nccc2ccc(Cl)nc12)C(F)(F)F>>Cc1csc(Nc2nccc3ccc(Cl)nc23)n1 | ClC1=NC2=C(N=CC=C2C=C1)OS(=O)(=O)C(F)(F)F.NC=1SC=C(N1)C>>ClC1=NC2=C(N=CC=C2C=C1)NC=1SC=C(N1)C | [CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:18]1.O=S(=O)(O[c:7]1[n:8][cH:9][cH:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[n:16][c:17]12)C(F)(F)F>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][cH:10][c:11]3[cH:12][cH:13][c:14]([Cl:15])[n:16][c:17]23)[n:18]1 | Cc1csc(N)n1.O=S(=O)(Oc1nccc2ccc(Cl)nc12)C(F)(F)F | Cc1csc(Nc2nccc3ccc(Cl)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ad91d46cc6a050540b70db82f4fdeba263271e8c440ace2e3cd9dffe02939637 | bb10fd1f8b4c076f7383c064536fdfc446f12f8f31783c2e83c5124ffdf8d8a7 | c1cnc2c(Nc3nccs3)nccc2c1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[NH2;D1;+0:8]-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1>>[c:5]:[c:4](:[#7;a:6]:[c:7]):[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[#7;a:13]:1):[#7;a:2]:[c:3] | null | [] | null | null | null | null | The title compound, MS: m/e=277 (M+H+), was prepared in accordance with the general method of example 1 from trifluoro-methanesulfonic acid 2-chloro-[1,7]naphthyridin-8-yl ester (Example G) and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Primary amine | Secondary amine | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1cscn1.c1cnc2cnccc2c1 | TfOH.HO- | null | null | null | Cc1csc(N)n1.O=S(=O)(Oc1nccc2ccc(Cl)nc12)C(F)(F)F>>Cc1csc(Nc2nccc3ccc(Cl)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f890bc82a5114a1087e119534befe52f | Cc1nc(N)cs1.O=S(=O)(Oc1nccc2ccc(Cl)nc12)C(F)(F)F>>Cc1nc(Nc2nccc3ccc(Cl)nc23)cs1 | ClC1=NC2=C(N=CC=C2C=C1)OS(=O)(=O)C(F)(F)F.NC=1N=C(SC1)C>>ClC1=NC2=C(N=CC=C2C=C1)NC=1N=C(SC1)C | [CH3:1][c:2]1[n:3][c:4]([NH2:5])[cH:17][s:18]1.O=S(=O)(O[c:6]1[n:7][cH:8][cH:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[n:15][c:16]12)C(F)(F)F>>[CH3:1][c:2]1[n:3][c:4]([NH:5][c:6]2[n:7][cH:8][cH:9][c:10]3[cH:11][cH:12][c:13]([Cl:14])[n:15][c:16]23)[cH:17][s:18]1 | Cc1nc(N)cs1.O=S(=O)(Oc1nccc2ccc(Cl)nc12)C(F)(F)F | Cc1nc(Nc2nccc3ccc(Cl)nc23)cs1 | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ad91d46cc6a050540b70db82f4fdeba263271e8c440ace2e3cd9dffe02939637 | bb10fd1f8b4c076f7383c064536fdfc446f12f8f31783c2e83c5124ffdf8d8a7 | c1cnc2c(Nc3cscn3)nccc2c1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].[NH2;D1;+0:8]-[c:9]1:[#7;a:10]:[c:11]:[#16;a:12]:[c:13]:1>>[c:5]:[c:4](:[#7;a:6]:[c:7]):[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9]1:[#7;a:10]:[c:11]:[#16;a:12]:[c:13]:1):[#7;a:2]:[c:3] | null | [] | null | null | null | null | The title compound, MS: m/e=277.0/279.1 (M+H+), was prepared in accordance with the general method of example 1 from trifluoro-methanesulfonic acid 2-chloro-[1,7]naphthyridin-8-yl ester (Example G) and 4-amino-2-methylthiazole (Example F).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Primary amine | Secondary amine | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1cscn1.c1cnc2cnccc2c1 | TfOH.HO- | null | null | null | Cc1nc(N)cs1.O=S(=O)(Oc1nccc2ccc(Cl)nc12)C(F)(F)F>>Cc1nc(Nc2nccc3ccc(Cl)nc23)cs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-450e80bcc42c4eca88a27fa08fd2eb33 | C[O-].Cc1csc(Nc2nccc3ccc(Cl)nc23)n1>>COc1ccc2ccnc(Nc3nc(C)cs3)c2n1 | ClC1=NC2=C(N=CC=C2C=C1)NC=1SC=C(N1)C.C[O-].[Na+]>>COC1=NC2=C(N=CC=C2C=C1)NC=1SC=C(N1)C | [CH3:1][O-:2].Cl[c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][n:9][c:10]([NH:11][c:12]3[n:13][c:14]([CH3:15])[cH:16][s:17]3)[c:18]2[n:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][n:9][c:10]([NH:11][c:12]3[n:13][c:14]([CH3:15])[cH:16][s:17]3)[c:18]2[n:19]1 | C[O-].Cc1csc(Nc2nccc3ccc(Cl)nc23)n1 | COc1ccc2ccnc(Nc3nc(C)cs3)c2n1 | null | null | S1(=O)(=O)CCCC1.O | Heteroatom Alkylation and Arylation | OtherReaction | ed549ea7bf277eeb8b3697ccd47fe641c45560609c0eddc48d7dd9c11f428437 | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1cnc2c(Nc3nccs3)nccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]):[c:6]:[c:7].[C;D1;H3:8]-[O-;H0;D1:9]>>[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[C;D1;H3:8]):[c:6]:[c:7] | 79 | [{"value": 79.0, "product": "COC1=NC2=C(N=CC=C2C=C1)NC=1SC=C(N1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.9, "product": "COC1=NC2=C(N=CC=C2C=C1)NC=1SC=C(N1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a solution of (2-chloro-[1,7]naphthyridin-8-yl)-(4-methyl-thiazol-2-yl)-amine (0.055 g, 0.20 mmol) in 1.5 ml sulfolane was added g sodium methylate (0.55, 1.0 mmol). The reaction mixture was heated for 10 min at 100° C. under microwave irradiation. The reaction mixture was diluted with water and extracted with three... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1cnc2cnccc2c1.c1cscn1 | Other | S1(=O)(=O)CCCC1.O | 100 | null | C[O-].Cc1csc(Nc2nccc3ccc(Cl)nc23)n1>S1(=O)(=O)CCCC1.O>COc1ccc2ccnc(Nc3nc(C)cs3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-14933857fb924fe7a32b63cd1e2c8b68 | Cc1csc(Nc2nccc3ccc(Cl)nc23)n1>>CCc1ccc2ccnc(Nc3nc(C)cs3)c2n1 | CCCCCC.ClC1=NC2=C(N=CC=C2C=C1)NC=1SC=C(N1)C.C(C)[Zn]CC>>C(C)C1=NC2=C(N=CC=C2C=C1)NC=1SC=C(N1)C | Cl[c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][n:9][c:10]([NH:11][c:12]3[n:13][c:14]([CH3:15])[cH:16][s:17]3)[c:18]2[n:19]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][n:9][c:10]([NH:11][c:12]3[n:13][c:14]([CH3:15])[cH:16][s:17]3)[c:18]2[n:19]1 | Cc1csc(Nc2nccc3ccc(Cl)nc23)n1 | CCc1ccc2ccnc(Nc3nc(C)cs3)c2n1 | 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 | O1CCCC1 | Functional Group Interconversion | OtherReaction | 98773c2547aed54ea1dd71d0ac6a4dbf8c36af7cd8980dd1183e0e7d65f3f1fd | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1cnc2c(Nc3nccs3)nccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]):[c:6]:[c:7]>>[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[C:8]-[C;D1;H3:9]):[c:6]:[c:7] | 28 | [{"value": 28.0, "product": "C(C)C1=NC2=C(N=CC=C2C=C1)NC=1SC=C(N1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (2-chloro-[1,7]naphthyridin-8-yl)-(4-methyl-thiazol-2-yl)-amine (0.055 g, 0.20 mmol) in 2 ml dry tetrahydrofuran (purged with argon) were subsequently added tetrakis(triphenylphosphine)palladium (0.011 g, 0.0095 mmol) and a 1.0 M solution of diethylzinc in n-hexane (0.4 ml, 0.4 mmol). The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cnc2cnccc2c1 | c1cnc2cnccc2c1 | c1cnc2cnccc2c1.c1cscn1 | 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.O1CCCC1 | null | null | Cc1csc(Nc2nccc3ccc(Cl)nc23)n1>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.O1CCCC1>CCc1ccc2ccnc(Nc3nc(C)cs3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-126026fb034148ac9862a5569f986898 | Cc1csc(N)n1.Clc1ncc(Br)c2cccnc12.OB(O)c1cncnc1>>Cc1csc(Nc2ncc(-c3cncnc3)c3cccnc23)n1 | BrC1=C2C=CC=NC2=C(N=C1)Cl.N1=CN=CC(=C1)B(O)O.NC=1SC=C(N1)C>>CC=1N=C(SC1)NC=1N=CC(=C2C=CC=NC12)C=1C=NC=NC1 | [CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:23]1.Cl[c:7]1[n:8][cH:9][c:10](Br)[c:17]2[cH:18][cH:19][cH:20][n:21][c:22]12.OB(O)[c:11]1[cH:12][n:13][cH:14][n:15][cH:16]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][n:13][cH:14][n:15][cH:16]3)[c:17]3[cH:18][cH:19][cH:20][n:21][c:22]23)[n:23]1 | Cc1csc(N)n1.Clc1ncc(Br)c2cccnc12.OB(O)c1cncnc1 | Cc1csc(Nc2ncc(-c3cncnc3)c3cccnc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4244081fc93cf0015a20104762a30e11c662ef9f6f0a107f9d9916fab9b5c60d | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3nccs3)ncc(-c3cncnc3)c2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c;H0;D3;+0:4](-Cl):[c:5](:[#7;a:6]:[c:7]):[c:8]:1:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:9]:[c:8]1:[c:5](:[#7;a:6]:[c:7]):[c;H0;D3;+0:4](-[NH;D2;+0:16]-[c:17]2:[#16;a:18]:[c:19]:[c:20]:[... | null | [] | null | null | null | null | The title compound, MS: m/e=321.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 5-bromo-8-chloro-[1,7]naphthyridine (Example H), 5-pyrimidineboronic acid and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1cncnc1 | c1cncnc1.c1cnc2cnccc2c1 | c1cscn1.c1cncnc1.c1cnc2cnccc2c1 | HCl.Br-.B | null | null | null | Cc1csc(N)n1.Clc1ncc(Br)c2cccnc12.OB(O)c1cncnc1>>Cc1csc(Nc2ncc(-c3cncnc3)c3cccnc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-411eba558a664c04b79f1f3db141366d | Cc1csc(N)n1.Clc1ncc(Br)c2cccnc12.OB(O)c1cccnc1>>Cc1csc(Nc2ncc(-c3cccnc3)c3cccnc23)n1 | BrC1=C2C=CC=NC2=C(N=C1)Cl.N1=CC=CC(=C1)B(O)O.NC=1SC=C(N1)C>>CC=1N=C(SC1)NC=1N=CC(=C2C=CC=NC12)C=1C=NC=CC1 | [CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:23]1.Cl[c:7]1[n:8][cH:9][c:10](Br)[c:17]2[cH:18][cH:19][cH:20][n:21][c:22]12.OB(O)[c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][n:15][cH:16]3)[c:17]3[cH:18][cH:19][cH:20][n:21][c:22]23)[n:23]... | Cc1csc(N)n1.Clc1ncc(Br)c2cccnc12.OB(O)c1cccnc1 | Cc1csc(Nc2ncc(-c3cccnc3)c3cccnc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3nccs3)c3ncccc23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c;H0;D3;+0:4](-Cl):[c:5](:[#7;a:6]:[c:7]):[c:8]:1:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:9]:[c:8]1:[c:5](:[#7;a:6]:[c:7]):[c;H0;D3;+0:4](-[NH;D2;+0:16]-[c:17]2:[#16;a:18]:[c:19]:[c:20]:[#7;... | null | [] | null | null | null | null | The title compound, MS: m/e=320.0 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 5-bromo-8-chloro-[1,7]naphthyridine (Example H), 5-pyridineboronic acid and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1cscn1.c1ccncc1.c1cnc2cnccc2c1 | HCl.Br-.B | null | null | null | Cc1csc(N)n1.Clc1ncc(Br)c2cccnc12.OB(O)c1cccnc1>>Cc1csc(Nc2ncc(-c3cccnc3)c3cccnc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0740054aff2446f588012d2b2a5ba8cd | Clc1ncc(Br)c2cccnc12.Cn1ccc(N)n1.OB(O)c1cccnc1>>Cn1ccc(Nc2ncc(-c3cccnc3)c3cccnc23)n1 | BrC1=C2C=CC=NC2=C(N=C1)Cl.N1=CC=CC(=C1)B(O)O.CN1N=C(C=C1)N>>CN1N=C(C=C1)NC=1N=CC(=C2C=CC=NC12)C=1C=NC=CC1 | Cl[c:7]1[n:8][cH:9][c:10](Br)[c:17]2[cH:18][cH:19][cH:20][n:21][c:22]12.[CH3:1][n:2]1[cH:3][cH:4][c:5]([NH2:6])[n:23]1.OB(O)[c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1>>[CH3:1][n:2]1[cH:3][cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][n:15][cH:16]3)[c:17]3[cH:18][cH:19][cH:20][n:21][c:22]23)[n:2... | Clc1ncc(Br)c2cccnc12.Cn1ccc(N)n1.OB(O)c1cccnc1 | Cn1ccc(Nc2ncc(-c3cccnc3)c3cccnc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3cc[nH]n3)c3ncccc23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c;H0;D3;+0:4](-Cl):[c:5](:[#7;a:6]:[c:7]):[c:8]:1:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1.[C;D1;H3:16]-[#7;a:17]1:[#7;a:18]:[c:19](-[NH2;D1;+0:20]):[c:21]:[c:22]:1>>[C;D1;H3:16]-[#7;a:17]1:[#7;a:18]:[c:19](-[NH;D2;+0:20]-[c;H0;D3;+0:4]2:[#7;a:3]:[c:2]:[c... | null | [] | null | null | null | null | The title compound, MS: m/e=303.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 5-bromo-8-chloro-[1,7]naphthyridine (Example H), 5-pyridineboronic acid and 1-methyl-1H-pyrazol-3-ylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1cc[nH]n1.c1ccncc1.c1cnc2cnccc2c1 | HCl.Br-.B | null | null | null | Clc1ncc(Br)c2cccnc12.Cn1ccc(N)n1.OB(O)c1cccnc1>>Cn1ccc(Nc2ncc(-c3cccnc3)c3cccnc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fd6575b9037a45eeb030e76a9944b47f | Cc1nc(N)cs1.Clc1ncc(Br)c2cccnc12.OB(O)c1cccnc1>>Cc1nc(Nc2ncc(-c3cccnc3)c3cccnc23)cs1 | BrC1=C2C=CC=NC2=C(N=C1)Cl.N1=CC=CC(=C1)B(O)O.NC=1N=C(SC1)C>>CC=1SC=C(N1)NC=1N=CC(=C2C=CC=NC12)C=1C=NC=CC1 | [CH3:1][c:2]1[n:3][c:4]([NH2:5])[cH:22][s:23]1.Cl[c:6]1[n:7][cH:8][c:9](Br)[c:16]2[cH:17][cH:18][cH:19][n:20][c:21]12.OB(O)[c:10]1[cH:11][cH:12][cH:13][n:14][cH:15]1>>[CH3:1][c:2]1[n:3][c:4]([NH:5][c:6]2[n:7][cH:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][n:14][cH:15]3)[c:16]3[cH:17][cH:18][cH:19][n:20][c:21]23)[cH:22][s:23]... | Cc1nc(N)cs1.Clc1ncc(Br)c2cccnc12.OB(O)c1cccnc1 | Cc1nc(Nc2ncc(-c3cccnc3)c3cccnc23)cs1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3cscn3)c3ncccc23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c;H0;D3;+0:4](-Cl):[c:5](:[#7;a:6]:[c:7]):[c:8]:1:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#7;a:18]:[c:19]:[#16;a:20]:[c:21]:1>>[c:9]:[c:8]1:[c:5](:[#7;a:6]:[c:7]):[c;H0;D3;+0:4](-[NH;D2;+0:16]-[c:17]2:[#7;a:18]:[c:19]:[#16;a:20]:[... | null | [] | null | null | null | null | The title compound, MS: m/e=320.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 5-bromo-8-chloro-[1,7]naphthyridine (Example H), 5-pyridineboronic acid and 4-amino-2-methylthiazole (Example F).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1cscn1.c1ccncc1.c1cnc2cnccc2c1 | HCl.Br-.B | null | null | null | Cc1nc(N)cs1.Clc1ncc(Br)c2cccnc12.OB(O)c1cccnc1>>Cc1nc(Nc2ncc(-c3cccnc3)c3cccnc23)cs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3427cc8164f7400fbf0bb2b25b3f21cf | Cc1nc(N)cs1.Clc1ncc(Br)c2cccnc12.OB(O)c1cncnc1>>Cc1nc(Nc2ncc(-c3cncnc3)c3cccnc23)cs1 | BrC1=C2C=CC=NC2=C(N=C1)Cl.N1=CN=CC(=C1)B(O)O.NC=1N=C(SC1)C>>CC=1SC=C(N1)NC=1N=CC(=C2C=CC=NC12)C=1C=NC=NC1 | [CH3:1][c:2]1[n:3][c:4]([NH2:5])[cH:22][s:23]1.Cl[c:6]1[n:7][cH:8][c:9](Br)[c:16]2[cH:17][cH:18][cH:19][n:20][c:21]12.OB(O)[c:10]1[cH:11][n:12][cH:13][n:14][cH:15]1>>[CH3:1][c:2]1[n:3][c:4]([NH:5][c:6]2[n:7][cH:8][c:9](-[c:10]3[cH:11][n:12][cH:13][n:14][cH:15]3)[c:16]3[cH:17][cH:18][cH:19][n:20][c:21]23)[cH:22][s:23]1 | Cc1nc(N)cs1.Clc1ncc(Br)c2cccnc12.OB(O)c1cncnc1 | Cc1nc(Nc2ncc(-c3cncnc3)c3cccnc23)cs1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4244081fc93cf0015a20104762a30e11c662ef9f6f0a107f9d9916fab9b5c60d | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3cscn3)ncc(-c3cncnc3)c2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c;H0;D3;+0:4](-Cl):[c:5](:[#7;a:6]:[c:7]):[c:8]:1:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#7;a:18]:[c:19]:[#16;a:20]:[c:21]:1>>[c:9]:[c:8]1:[c:5](:[#7;a:6]:[c:7]):[c;H0;D3;+0:4](-[NH;D2;+0:16]-[c:17]2:[#7;a:18]:[c:19]:[#16;a:20... | null | [] | null | null | null | null | The title compound, MS: m/e=321.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 5-bromo-8-chloro-[1,7]naphthyridine (Example H), 5-pyrimidineboronic acid and 4-amino-2-methylthiazole (Example F).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1cncnc1 | c1cncnc1.c1cnc2cnccc2c1 | c1cscn1.c1cncnc1.c1cnc2cnccc2c1 | HCl.Br-.B | null | null | null | Cc1nc(N)cs1.Clc1ncc(Br)c2cccnc12.OB(O)c1cncnc1>>Cc1nc(Nc2ncc(-c3cncnc3)c3cccnc23)cs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cac6be2d6fc7493b92cebf7e16bb87d5 | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1cccnc1>>Cc1csc(Nc2ncc(-c3cccnc3)c3ccc(C)nc23)n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.N1=CC(=CC=C1)B(O)O.NC=1SC=C(N1)C>>CC1=NC2=C(N=CC(=C2C=C1)C=1C=NC=CC1)NC=1SC=C(N1)C | Cl[c:7]1[n:8][cH:9][c:10](I)[c:17]2[cH:18][cH:19][c:20]([CH3:21])[n:22][c:23]12.[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:24]1.OB(O)[c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][n:15][cH:16]3)[c:17]3[cH:18][cH:19][c:20]([CH3:21])[n:2... | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1cccnc1 | Cc1csc(Nc2ncc(-c3cccnc3)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3nccs3)c3ncccc23)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:6]:[c:5]1:[c:7](:[#7;a:8]:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:16]-[c:17]2:[#16;a:18]:[c:19]:[c:20]:[#7;a... | null | [] | null | null | null | null | The title compound, MS: m/e=334.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 3-pyridineboronic acid and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1cscn1.c1ccncc1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1cccnc1>>Cc1csc(Nc2ncc(-c3cccnc3)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3b92ed255f6441148c52dd03745aac81 | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1ccc(F)cn1.OB(O)c1cccnc1>>Cc1ccc2c(-c3cccnc3)cnc(Nc3ccc(F)cn3)c2n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.N1=CC(=CC=C1)B(O)O.NC1=NC=C(C=C1)F>>FC=1C=CC(=NC1)NC=1N=CC(=C2C=CC(=NC12)C)C=1C=NC=CC1 | Cl[c:15]1[n:14][cH:13][c:6](I)[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:25][c:24]21.[NH2:16][c:17]1[cH:18][cH:19][c:20]([F:21])[cH:22][n:23]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][cH:10][n:11][cH:12]3)[cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][cH:19][c:20]([F:21]... | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1ccc(F)cn1.OB(O)c1cccnc1 | Cc1ccc2c(-c3cccnc3)cnc(Nc3ccc(F)cn3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1ccc(Nc2ncc(-c3cccnc3)c3cccnc23)nc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17](:[c:18]):[#7;a:19]:[c:20]>>[c:18]:[c:17](-[NH;D2;+0:16]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[c:13]... | null | [] | null | null | null | null | The title compound, MS: m/e=332.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 3-pyridineboronic acid and 2-amino-5-fluoropyridine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1ccncc1.c1cnc2cnccc2c1.c1ccncc1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1ccc(F)cn1.OB(O)c1cccnc1>>Cc1ccc2c(-c3cccnc3)cnc(Nc3ccc(F)cn3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eab36bf0923444048c7ba053e52f9259 | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nc(N)cs1.OB(O)c1cccnc1>>Cc1ccc2c(-c3cccnc3)cnc(Nc3csc(C)n3)c2n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.N1=CC(=CC=C1)B(O)O.NC=1N=C(SC1)C>>CC1=NC2=C(N=CC(=C2C=C1)C=1C=NC=CC1)NC=1N=C(SC1)C | Cl[c:15]1[n:14][cH:13][c:6](I)[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:24][c:23]21.[NH2:16][c:17]1[cH:18][s:19][c:20]([CH3:21])[n:22]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][cH:10][n:11][cH:12]3)[cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][s:19][c:20]([CH3:21])[n:2... | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nc(N)cs1.OB(O)c1cccnc1 | Cc1ccc2c(-c3cccnc3)cnc(Nc3csc(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3cscn3)c3ncccc23)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#7;a:18]:[c:19]:[#16;a:20]:[c:21]:1>>[c:9]:[#7;a:8]:[c:7]1:[c:5](:[c:6]):[c;H0;D3;+0:4](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:1... | null | [] | null | null | null | null | The title compound, MS: m/e=334.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 3-pyridineboronic acid and 4-amino-2-methylthiazole (Example F).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1ccncc1.c1cnc2cnccc2c1.c1cscn1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nc(N)cs1.OB(O)c1cccnc1>>Cc1ccc2c(-c3cccnc3)cnc(Nc3csc(C)n3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a347eff16674c3f923f542f868c5fee | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1ccnc(Cl)c1.OB(O)c1cccnc1>>Cc1ccc2c(-c3cccnc3)cnc(Nc3ccnc(Cl)c3)c2n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.N1=CC(=CC=C1)B(O)O.ClC1=NC=CC(=C1)N>>ClC1=NC=CC(=C1)NC=1N=CC(=C2C=CC(=NC12)C)C=1C=NC=CC1 | Cl[c:15]1[n:14][cH:13][c:6](I)[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:25][c:24]21.[NH2:16][c:17]1[cH:18][cH:19][n:20][c:21]([Cl:22])[cH:23]1.OB(O)[c:7]1[cH:8][cH:9][cH:10][n:11][cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][cH:10][n:11][cH:12]3)[cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][cH:19][n:20][c:21]... | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1ccnc(Cl)c1.OB(O)c1cccnc1 | Cc1ccc2c(-c3cccnc3)cnc(Nc3ccnc(Cl)c3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3ccncc3)c3ncccc23)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[c:18]:[c:19]:[#7;a:20]:[c:21]:[c:22]:1>>[c:9]:[#7;a:8]:[c:7]1:[c:5](:[c:6]):[c;H0;D3;+0:4](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[c:13]:[c:14]:[... | null | [] | null | null | null | null | The title compound, MS: m/e=348.2/350.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 3-pyridineboronic acid and 2-chloro-4-aminopyridine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1ccncc1.c1cnc2cnccc2c1.c1ccncc1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1ccnc(Cl)c1.OB(O)c1cccnc1>>Cc1ccc2c(-c3cccnc3)cnc(Nc3ccnc(Cl)c3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a407114103ed48cda5d83d1ca95f927a | COc1cccc(B(O)O)c1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1>>COc1cccc(-c2cnc(Nc3nc(C)cs3)c3nc(C)ccc23)c1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.COC=1C=C(C=CC1)B(O)O.NC=1SC=C(N1)C>>COC=1C=C(C=CC1)C1=C2C=CC(=NC2=C(N=C1)NC=1SC=C(N1)C)C | OB(O)[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:26]1.Cl[c:11]1[n:10][cH:9][c:8](I)[c:25]2[c:19]1[n:20][c:21]([CH3:22])[cH:23][cH:24]2.[NH2:12][c:13]1[n:14][c:15]([CH3:16])[cH:17][s:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10][c:11]([NH:12][c:13]3[n:14][c:15]([CH3:16])[cH:17][s:18]3)[c:19]3[n:... | COc1cccc(B(O)O)c1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1 | COc1cccc(-c2cnc(Nc3nc(C)cs3)c3nc(C)ccc23)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 117bb42e263c78d4972cfd9400f5c94ee60c425fe51a73efd45cb9b04229693d | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1ccc(-c2cnc(Nc3nccs3)c3ncccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[NH2;D1;+0:15]-[c:16]1:[#16;a:17]:[c:18]:[c:19]:[#7;a:20]:1>>[c:9]:[#7;a:8]:[c:7]1:[c:5](:[c:6]):[c;H0;D3;+0:4](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[c:3]:[#7;a:2]:[... | null | [] | null | null | null | null | The title compound, MS: m/e=363.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 3-methoxyphenylboronic acid and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1ccccc1.c1cnc2cnccc2c1 | c1ccccc1.c1cnc2cnccc2c1 | c1ccccc1.c1cscn1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | COc1cccc(B(O)O)c1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1>>COc1cccc(-c2cnc(Nc3nc(C)cs3)c3nc(C)ccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c178662875c94cb994b137464d585260 | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1cccc(C(F)(F)F)c1>>Cc1csc(Nc2ncc(-c3cccc(C(F)(F)F)c3)c3ccc(C)nc23)n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.FC(C=1C=C(C=CC1)B(O)O)(F)F.NC=1SC=C(N1)C>>CC=1N=C(SC1)NC=1N=CC(=C2C=CC(=NC12)C)C1=CC(=CC=C1)C(F)(F)F | Cl[c:7]1[n:8][cH:9][c:10](I)[c:21]2[cH:22][cH:23][c:24]([CH3:25])[n:26][c:27]12.[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:28]1.OB(O)[c:11]1[cH:12][cH:13][cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][c:15]([C:16]([F:17])([F:1... | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1cccc(C(F)(F)F)c1 | Cc1csc(Nc2ncc(-c3cccc(C(F)(F)F)c3)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 117bb42e263c78d4972cfd9400f5c94ee60c425fe51a73efd45cb9b04229693d | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1ccc(-c2cnc(Nc3nccs3)c3ncccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[NH2;D1;+0:15]-[c:16]1:[#16;a:17]:[c:18]:[c:19]:[#7;a:20]:1>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:15]-[c:16]2:[#16;a:17]:[c:1... | null | [] | null | null | null | null | The title compound, MS: m/e=401.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 3-(trifluoromethyl)phenylboronic acid and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccccc1 | c1ccccc1.c1cnc2cnccc2c1 | c1cscn1.c1ccccc1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1cccc(C(F)(F)F)c1>>Cc1csc(Nc2ncc(-c3cccc(C(F)(F)F)c3)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff9ffbf26f7e49d2b69a8e069fa50e22 | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nc(N)cs1.OB(O)c1cncnc1>>Cc1ccc2c(-c3cncnc3)cnc(Nc3csc(C)n3)c2n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.N1=CN=CC(=C1)B(O)O.NC=1N=C(SC1)C>>CC1=NC2=C(N=CC(=C2C=C1)C=1C=NC=NC1)NC=1N=C(SC1)C | Cl[c:15]1[n:14][cH:13][c:6](I)[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:24][c:23]21.[NH2:16][c:17]1[cH:18][s:19][c:20]([CH3:21])[n:22]1.OB(O)[c:7]1[cH:8][n:9][cH:10][n:11][cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][n:9][cH:10][n:11][cH:12]3)[cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][s:19][c:20]([CH3:21])[n:22]... | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nc(N)cs1.OB(O)c1cncnc1 | Cc1ccc2c(-c3cncnc3)cnc(Nc3csc(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4244081fc93cf0015a20104762a30e11c662ef9f6f0a107f9d9916fab9b5c60d | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3cscn3)ncc(-c3cncnc3)c2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#7;a:18]:[c:19]:[#16;a:20]:[c:21]:1>>[c:9]:[#7;a:8]:[c:7]1:[c:5](:[c:6]):[c;H0;D3;+0:4](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[c:13]:[#7;a:14... | null | [] | null | null | null | null | The title compound, MS: m/e=335.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 5-pyrimidineboronic acid and 4-amino-2-methylthiazole (Example F).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1cncnc1 | c1cncnc1.c1cnc2cnccc2c1 | c1cncnc1.c1cnc2cnccc2c1.c1cscn1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nc(N)cs1.OB(O)c1cncnc1>>Cc1ccc2c(-c3cncnc3)cnc(Nc3csc(C)n3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-49090720f4af4bad98f01904fd8727ca | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nc(N)cs1.OB(O)c1ccc(Cl)nc1>>Cc1ccc2c(-c3ccc(Cl)nc3)cnc(Nc3csc(C)n3)c2n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.ClC1=NC=C(C=C1)B(O)O.NC=1N=C(SC1)C>>ClC1=CC=C(C=N1)C1=C2C=CC(=NC2=C(N=C1)NC=1N=C(SC1)C)C | Cl[c:16]1[n:15][cH:14][c:6](I)[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:25][c:24]21.[NH2:17][c:18]1[cH:19][s:20][c:21]([CH3:22])[n:23]1.OB(O)[c:7]1[cH:8][cH:9][c:10]([Cl:11])[n:12][cH:13]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([Cl:11])[n:12][cH:13]3)[cH:14][n:15][c:16]([NH:17][c:18]3[cH:19][s:20][c:2... | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nc(N)cs1.OB(O)c1ccc(Cl)nc1 | Cc1ccc2c(-c3ccc(Cl)nc3)cnc(Nc3csc(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3cscn3)c3ncccc23)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#7;a:18]:[c:19]:[#16;a:20]:[c:21]:1>>[c:9]:[#7;a:8]:[c:7]1:[c:5](:[c:6]):[c;H0;D3;+0:4](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:1... | null | [] | null | null | null | null | The title compound, MS: m/e=368.0 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 2-chloro-5-pyridineboronic acid and 4-amino-2-methylthiazole (Example F).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1ccncc1.c1cnc2cnccc2c1.c1cscn1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nc(N)cs1.OB(O)c1ccc(Cl)nc1>>Cc1ccc2c(-c3ccc(Cl)nc3)cnc(Nc3csc(C)n3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-284ffe250bfa4225abfe6ba4b76c6e8f | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1ccc(Cl)nc1>>Cc1csc(Nc2ncc(-c3ccc(Cl)nc3)c3ccc(C)nc23)n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.ClC1=NC=C(C=C1)B(O)O.NC=1SC=C(N1)C>>ClC1=CC=C(C=N1)C1=C2C=CC(=NC2=C(N=C1)NC=1SC=C(N1)C)C | Cl[c:7]1[n:8][cH:9][c:10](I)[c:18]2[cH:19][cH:20][c:21]([CH3:22])[n:23][c:24]12.[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:25]1.OB(O)[c:11]1[cH:12][cH:13][c:14]([Cl:15])[n:16][cH:17]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([Cl:15])[n:16][cH:17]3)[c:18]3[cH:19][cH:20][c:2... | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1ccc(Cl)nc1 | Cc1csc(Nc2ncc(-c3ccc(Cl)nc3)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3nccs3)c3ncccc23)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:6]:[c:5]1:[c:7](:[#7;a:8]:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:16]-[c:17]2:[#16;a:18]:[c:19]:[c:20]:[#7;a... | null | [] | null | null | null | null | The title compound, MS: m/e=368.1 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 2-chloro-5-pyridineboronic acid and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1cscn1.c1ccncc1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1ccc(Cl)nc1>>Cc1csc(Nc2ncc(-c3ccc(Cl)nc3)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1806a059892481980d624ecc85db751 | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.Cc1noc(C)c1B(O)O>>Cc1csc(Nc2ncc(-c3c(C)noc3C)c3ccc(C)nc23)n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.CC1=NOC(=C1B(O)O)C.NC=1SC=C(N1)C>>CC1=NOC(=C1C1=C2C=CC(=NC2=C(N=C1)NC=1SC=C(N1)C)C)C | Cl[c:7]1[n:8][cH:9][c:10](I)[c:18]2[cH:19][cH:20][c:21]([CH3:22])[n:23][c:24]12.[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:25]1.OB(O)[c:11]1[c:12]([CH3:13])[n:14][o:15][c:16]1[CH3:17]>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[c:12]([CH3:13])[n:14][o:15][c:16]3[CH3:17])[c:18]3[cH:19][cH:20][c:2... | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.Cc1noc(C)c1B(O)O | Cc1csc(Nc2ncc(-c3c(C)noc3C)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f5b7db0360d3103ef36380174e1d61c11cd883755146172aa8be1e12acf1f24d | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3nccs3)ncc(-c3cnoc3)c2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11](-[C;D1;H3:12]):[#7;a:13]:[#8;a:14]:[c:15]:1-[C;D1;H3:16].[NH2;D1;+0:17]-[c:18]1:[#16;a:19]:[c:20]:[c:21]:[#7;a:22]:1>>[C;D1;H3:12]-[c:11]1:[#7;a:13]:[#8;a:14]:[c:15](-[C;D1;H3:16]):[c;H0;D3;+0:10]:1... | null | [] | null | null | null | null | The title compound, MS: m/e=352.3 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 3,5-dimethyl-isoxazole-4-boronic acid and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1cnoc1 | c1cnoc1.c1cnc2cnccc2c1 | c1cscn1.c1cnoc1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.Cc1noc(C)c1B(O)O>>Cc1csc(Nc2ncc(-c3c(C)noc3C)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3a718bd1b48241e884f1fb3f74be1699 | Cc1cc(B(O)O)n(C)n1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1>>Cc1csc(Nc2ncc(-c3cc(C)nn3C)c3ccc(C)nc23)n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.CN1N=C(C=C1B(O)O)C.NC=1SC=C(N1)C>>CN1N=C(C=C1C1=C2C=CC(=NC2=C(N=C1)NC=1SC=C(N1)C)C)C | OB(O)[c:11]1[cH:12][c:13]([CH3:14])[n:15][n:16]1[CH3:17].Cl[c:7]1[n:8][cH:9][c:10](I)[c:18]2[cH:19][cH:20][c:21]([CH3:22])[n:23][c:24]12.[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:25]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][c:13]([CH3:14])[n:15][n:16]3[CH3:17])[c:18]3[cH:19][cH:20][c... | Cc1cc(B(O)O)n(C)n1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1 | Cc1csc(Nc2ncc(-c3cc(C)nn3C)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1db5ab63aab22f28a1b1f0861587bde4bafc83e5a9b1180b7d2ddfbaedff9645 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3nccs3)ncc(-c3ccn[nH]3)c2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12](-[C;D1;H3:13]):[#7;a:14]:[#7;a:15]:1-[C;D1;H3:16].[NH2;D1;+0:17]-[c:18]1:[#16;a:19]:[c:20]:[c:21]:[#7;a:22]:1>>[C;D1;H3:13]-[c:12]1:[#7;a:14]:[#7;a:15](-[C;D1;H3:16]):[c;H0;D3;+0:10](-[c;H0;D... | null | [] | null | null | null | null | The title compound, MS: m/e=351.3 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 1,3-dimethyl-1H-pyrazole-5-boronic acid (Example J) and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cc[nH]n1.c1cnc2cnccc2c1 | c1cc[nH]n1.c1cnc2cnccc2c1 | c1cscn1.c1cc[nH]n1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | Cc1cc(B(O)O)n(C)n1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1>>Cc1csc(Nc2ncc(-c3cc(C)nn3C)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ac3fdb2e11c45ecb858c06e97b2f356 | CC1(C)OB(c2ccc(C#N)nc2)OC1(C)C.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1>>Cc1csc(Nc2ncc(-c3ccc(C#N)nc3)c3ccc(C)nc23)n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.C(#N)C1=NC=C(C=C1)B1OC(C)(C)C(C)(C)O1.NC=1SC=C(N1)C>>CC1=NC2=C(N=CC(=C2C=C1)C=1C=CC(=NC1)C#N)NC=1SC=C(N1)C | CC1(C)OB([c:11]2[cH:12][cH:13][c:14]([C:15]#[N:16])[n:17][cH:18]2)OC1(C)C.Cl[c:7]1[n:8][cH:9][c:10](I)[c:19]2[cH:20][cH:21][c:22]([CH3:23])[n:24][c:25]12.[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:26]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([C:15]#[N:16])[n:17][cH:18]3)[... | CC1(C)OB(c2ccc(C#N)nc2)OC1(C)C.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1 | Cc1csc(Nc2ncc(-c3ccc(C#N)nc3)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 020e0487e0430b94f5c6b65305d4ffd9178757c503bba4d0387d9e232a40d42f | ce1e7614cf8e78a20760526f234cf5f9619b7c4aeac68f90c4799bf68c2f9a2b | c1cncc(-c2cnc(Nc3nccs3)c3ncccc23)c1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:2)-O-C-1(-C)-C.Cl-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9]:[c;H0;D3;+0:10](-I):[c:11](:[c:12]):[c:13]:1:[#7;a:14]:[c:15].[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:12]:[c:11]1:[c:13](:[#7;a:14]:[c:15]):[c;H0;D3;+0:7](-[NH;D2;+0:16]-[c:17]2:[#16;a... | null | [] | null | null | null | null | The title compound, MS: m/e=359.1 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 2-cyanopyridine-5-boronic acid pinacol ester and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic ester | Secondary amine | B1OCCO1.c1ccncc1.c1cnc2cnccc2c1 | c1ccncc1.c1cnc2cnccc2c1 | c1cscn1.c1ccncc1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | CC1(C)OB(c2ccc(C#N)nc2)OC1(C)C.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1>>Cc1csc(Nc2ncc(-c3ccc(C#N)nc3)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fd215a531ec049e38574871df42012a0 | CS(=O)(=O)c1cccc(B(O)O)c1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1>>Cc1csc(Nc2ncc(-c3cccc(S(C)(=O)=O)c3)c3ccc(C)nc23)n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.CS(=O)(=O)C=1C=C(C=CC1)B(O)O.NC=1SC=C(N1)C>>CS(=O)(=O)C=1C=C(C=CC1)C1=C2C=CC(=NC2=C(N=C1)NC=1SC=C(N1)C)C | OB(O)[c:11]1[cH:12][cH:13][cH:14][c:15]([S:16]([CH3:17])(=[O:18])=[O:19])[cH:20]1.Cl[c:7]1[n:8][cH:9][c:10](I)[c:21]2[cH:22][cH:23][c:24]([CH3:25])[n:26][c:27]12.[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:28]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][c:15]([S:16]([CH3:17]... | CS(=O)(=O)c1cccc(B(O)O)c1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1 | Cc1csc(Nc2ncc(-c3cccc(S(C)(=O)=O)c3)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 117bb42e263c78d4972cfd9400f5c94ee60c425fe51a73efd45cb9b04229693d | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1ccc(-c2cnc(Nc3nccs3)c3ncccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[NH2;D1;+0:15]-[c:16]1:[#16;a:17]:[c:18]:[c:19]:[#7;a:20]:1>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:15]-[c:16]2:[#16;a:17]:[c:1... | null | [] | null | null | null | null | The title compound, MS: m/e=411.1 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), (3-methylsulfonylphenyl)boronic acid and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1ccccc1.c1cnc2cnccc2c1 | c1ccccc1.c1cnc2cnccc2c1 | c1cscn1.c1ccccc1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | CS(=O)(=O)c1cccc(B(O)O)c1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1>>Cc1csc(Nc2ncc(-c3cccc(S(C)(=O)=O)c3)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d71cd4e9df4c4766abed69d5238539ff | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1cncnc1>>Cc1csc(Nc2ncc(-c3cncnc3)c3ccc(C)nc23)n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.N1=CN=CC(=C1)B(O)O.NC=1SC=C(N1)C>>CC1=NC2=C(N=CC(=C2C=C1)C=1C=NC=NC1)NC=1SC=C(N1)C | Cl[c:7]1[n:8][cH:9][c:10](I)[c:17]2[cH:18][cH:19][c:20]([CH3:21])[n:22][c:23]12.[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:24]1.OB(O)[c:11]1[cH:12][n:13][cH:14][n:15][cH:16]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][n:13][cH:14][n:15][cH:16]3)[c:17]3[cH:18][cH:19][c:20]([CH3:21])[n:22]... | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1cncnc1 | Cc1csc(Nc2ncc(-c3cncnc3)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4244081fc93cf0015a20104762a30e11c662ef9f6f0a107f9d9916fab9b5c60d | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3nccs3)ncc(-c3cncnc3)c2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:6]:[c:5]1:[c:7](:[#7;a:8]:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:16]-[c:17]2:[#16;a:18]:[c:19]:[c:20]:[#... | null | [] | null | null | null | null | The title compound, MS: m/e=335.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 5-pyrimidineboronic acid and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1cncnc1 | c1cncnc1.c1cnc2cnccc2c1 | c1cscn1.c1cncnc1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1cncnc1>>Cc1csc(Nc2ncc(-c3cncnc3)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a87c6e41ec94d0b8511c2cdb4f970f6 | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1ccncc1>>Cc1csc(Nc2ncc(-c3ccncc3)c3ccc(C)nc23)n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.N1=CC=C(C=C1)B(O)O.NC=1SC=C(N1)C>>CC1=NC2=C(N=CC(=C2C=C1)C1=CC=NC=C1)NC=1SC=C(N1)C | Cl[c:7]1[n:8][cH:9][c:10](I)[c:17]2[cH:18][cH:19][c:20]([CH3:21])[n:22][c:23]12.[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:24]1.OB(O)[c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][n:14][cH:15][cH:16]3)[c:17]3[cH:18][cH:19][c:20]([CH3:21])[n:2... | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1ccncc1 | Cc1csc(Nc2ncc(-c3ccncc3)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3nccs3)ncc(-c3ccncc3)c2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:6]:[c:5]1:[c:7](:[#7;a:8]:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:16]-[c:17]2:[#16;a:18]:[c:19]:[c:20]:[#7;a... | null | [] | null | null | null | null | The title compound, MS: m/e=334.1 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 4-pyridineboronic acid and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1cscn1.c1ccncc1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1ccncc1>>Cc1csc(Nc2ncc(-c3ccncc3)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f21362cf2e6849859ccf39fb6c5fcbb1 | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1ccncc1B(O)O.Cc1csc(N)n1>>Cc1csc(Nc2ncc(-c3cnccc3C)c3ccc(C)nc23)n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.CC1=C(C=NC=C1)B(O)O.NC=1SC=C(N1)C>>CC1=NC2=C(N=CC(=C2C=C1)C=1C=NC=CC1C)NC=1SC=C(N1)C | Cl[c:7]1[n:8][cH:9][c:10](I)[c:18]2[cH:19][cH:20][c:21]([CH3:22])[n:23][c:24]12.OB(O)[c:11]1[cH:12][n:13][cH:14][cH:15][c:16]1[CH3:17].[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:25]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][n:13][cH:14][cH:15][c:16]3[CH3:17])[c:18]3[cH:19][cH:20][c:21]... | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1ccncc1B(O)O.Cc1csc(N)n1 | Cc1csc(Nc2ncc(-c3cnccc3C)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3nccs3)c3ncccc23)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:1-[C;D1;H3:16].[NH2;D1;+0:17]-[c:18]1:[#16;a:19]:[c:20]:[c:21]:[#7;a:22]:1>>[C;D1;H3:16]-[c:15]1:[c:14]:[c:13]:[#7;a:12]:[c:11]:[c;H0;D3;+0:10]:1-[c;H0;D3;+0:4]1:[c:3]... | null | [] | null | null | null | null | The title compound, MS: m/e=348.1 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 4-methylpyridine-3-boronic acid and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1cscn1.c1ccncc1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1ccncc1B(O)O.Cc1csc(N)n1>>Cc1csc(Nc2ncc(-c3cnccc3C)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a65e17341233443f9f31a4ef6ab9fa96 | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1ccc(F)nc1>>Cc1csc(Nc2ncc(-c3ccc(F)nc3)c3ccc(C)nc23)n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.FC1=NC=C(C=C1)B(O)O.NC=1SC=C(N1)C>>FC1=CC=C(C=N1)C1=C2C=CC(=NC2=C(N=C1)NC=1SC=C(N1)C)C | Cl[c:7]1[n:8][cH:9][c:10](I)[c:18]2[cH:19][cH:20][c:21]([CH3:22])[n:23][c:24]12.[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:25]1.OB(O)[c:11]1[cH:12][cH:13][c:14]([F:15])[n:16][cH:17]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([F:15])[n:16][cH:17]3)[c:18]3[cH:19][cH:20][c:21]... | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1ccc(F)nc1 | Cc1csc(Nc2ncc(-c3ccc(F)nc3)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3nccs3)c3ncccc23)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[c:13]:[#7;a:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:6]:[c:5]1:[c:7](:[#7;a:8]:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:16]-[c:17]2:[#16;a:18]:[c:19]:[c:20]:[#7;a... | null | [] | null | null | null | null | The title compound, MS: m/e=352.1 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 2-fluoropyridine-5-boronic acid and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1cscn1.c1ccncc1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1ccc(F)nc1>>Cc1csc(Nc2ncc(-c3ccc(F)nc3)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da6ac694788a4813beec245acb7b4bbe | COc1ccc(B(O)O)cn1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1>>COc1ccc(-c2cnc(Nc3nc(C)cs3)c3nc(C)ccc23)cn1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.COC1=NC=C(C=C1)B(O)O.NC=1SC=C(N1)C>>COC1=CC=C(C=N1)C1=C2C=CC(=NC2=C(N=C1)NC=1SC=C(N1)C)C | OB(O)[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[n:26][cH:25]1.Cl[c:10]1[n:9][cH:8][c:7](I)[c:24]2[c:18]1[n:19][c:20]([CH3:21])[cH:22][cH:23]2.[NH2:11][c:12]1[n:13][c:14]([CH3:15])[cH:16][s:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]([NH:11][c:12]3[n:13][c:14]([CH3:15])[cH:16][s:17]3)[c:18]3[n:19][c:20... | COc1ccc(B(O)O)cn1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1 | COc1ccc(-c2cnc(Nc3nc(C)cs3)c3nc(C)ccc23)cn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3nccs3)c3ncccc23)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:9]:[#7;a:8]:[c:7]1:[c:5](:[c:6]):[c;H0;D3;+0:4](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:1... | null | [] | null | null | null | null | The title compound, MS: m/e=364.1 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 2-methoxypyridine-5-boronic acid and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1ccncc1.c1cnc2cnccc2c1 | c1ccncc1.c1cnc2cnccc2c1 | c1ccncc1.c1cscn1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | COc1ccc(B(O)O)cn1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1>>COc1ccc(-c2cnc(Nc3nc(C)cs3)c3nc(C)ccc23)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e6ab16a4655941c0aaf655306c68602f | COc1cncc(B2OC(C)(C)C(C)(C)O2)c1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1>>COc1cncc(-c2cnc(Nc3nc(C)cs3)c3nc(C)ccc23)c1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.COC=1C=NC=C(C1)B1OC(C)(C)C(C)(C)O1.NC=1SC=C(N1)C>>COC=1C=C(C=NC1)C1=C2C=CC(=NC2=C(N=C1)NC=1SC=C(N1)C)C | CC1(C)OB([c:7]2[cH:6][n:5][cH:4][c:3]([O:2][CH3:1])[cH:26]2)OC1(C)C.Cl[c:11]1[n:10][cH:9][c:8](I)[c:25]2[c:19]1[n:20][c:21]([CH3:22])[cH:23][cH:24]2.[NH2:12][c:13]1[n:14][c:15]([CH3:16])[cH:17][s:18]1>>[CH3:1][O:2][c:3]1[cH:4][n:5][cH:6][c:7](-[c:8]2[cH:9][n:10][c:11]([NH:12][c:13]3[n:14][c:15]([CH3:16])[cH:17][s:18]3)... | COc1cncc(B2OC(C)(C)C(C)(C)O2)c1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1 | COc1cncc(-c2cnc(Nc3nc(C)cs3)c3nc(C)ccc23)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 020e0487e0430b94f5c6b65305d4ffd9178757c503bba4d0387d9e232a40d42f | ce1e7614cf8e78a20760526f234cf5f9619b7c4aeac68f90c4799bf68c2f9a2b | c1cncc(-c2cnc(Nc3nccs3)c3ncccc23)c1 | C-C1(-C)-O-B(-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:2)-O-C-1(-C)-C.Cl-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9]:[c;H0;D3;+0:10](-I):[c:11](:[c:12]):[c:13]:1:[#7;a:14]:[c:15].[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:15]:[#7;a:14]:[c:13]1:[c:11](:[c:12]):[c;H0;D3;+0:10](-[c;H0;D3;+0:1]2:[c:2]:[c:3]... | null | [] | null | null | null | null | The title compound, MS: m/e=364.1 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 3-methoxy-5-pyridineboronic acid pinacol ester and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic ester | Secondary amine | B1OCCO1.c1ccncc1.c1cnc2cnccc2c1 | c1ccncc1.c1cnc2cnccc2c1 | c1ccncc1.c1cscn1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | COc1cncc(B2OC(C)(C)C(C)(C)O2)c1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1>>COc1cncc(-c2cnc(Nc3nc(C)cs3)c3nc(C)ccc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e4c0d1a6065b4a09a196a771daeb1cdd | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1cccnc1B(O)O.Cc1csc(N)n1>>Cc1csc(Nc2ncc(-c3ncccc3C)c3ccc(C)nc23)n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.CC=1C(=NC=CC1)B(O)O.NC=1SC=C(N1)C>>CC1=NC2=C(N=CC(=C2C=C1)C1=NC=CC=C1C)NC=1SC=C(N1)C | Cl[c:7]1[n:8][cH:9][c:10](I)[c:18]2[cH:19][cH:20][c:21]([CH3:22])[n:23][c:24]12.OB(O)[c:11]1[n:12][cH:13][cH:14][cH:15][c:16]1[CH3:17].[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:25]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[n:12][cH:13][cH:14][cH:15][c:16]3[CH3:17])[c:18]3[cH:19][cH:20][c:21]... | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1cccnc1B(O)O.Cc1csc(N)n1 | Cc1csc(Nc2ncc(-c3ncccc3C)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1ccc(-c2cnc(Nc3nccs3)c3ncccc23)nc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[c:13](-[C;D1;H3:14]):[c:15].[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[C;D1;H3:14]-[c:13](:[c:15]):[c;H0;D3;+0:10](-[c;H0;D3;+0:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;... | null | [] | null | null | null | null | The title compound, MS: m/e=348.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 3-methylpyridine-2-boronic acid and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1cscn1.c1ccncc1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1cccnc1B(O)O.Cc1csc(N)n1>>Cc1csc(Nc2ncc(-c3ncccc3C)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b73d9c8c08aa4d90ab4f6fb64d5e25b7 | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1nc(C(F)(F)F)cs1.OB(O)c1cncnc1>>Cc1ccc2c(-c3cncnc3)cnc(Nc3nc(C(F)(F)F)cs3)c2n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.N1=CN=CC(=C1)B(O)O.NC=1SC=C(N1)C(F)(F)F>>CC1=NC2=C(N=CC(=C2C=C1)C=1C=NC=NC1)NC=1SC=C(N1)C(F)(F)F | Cl[c:15]1[n:14][cH:13][c:6](I)[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:27][c:26]21.[NH2:16][c:17]1[n:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][s:25]1.OB(O)[c:7]1[cH:8][n:9][cH:10][n:11][cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][n:9][cH:10][n:11][cH:12]3)[cH:13][n:14][c:15]([NH:16][c:17]3[n:18][c:19]([C... | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1nc(C(F)(F)F)cs1.OB(O)c1cncnc1 | Cc1ccc2c(-c3cncnc3)cnc(Nc3nc(C(F)(F)F)cs3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4244081fc93cf0015a20104762a30e11c662ef9f6f0a107f9d9916fab9b5c60d | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3nccs3)ncc(-c3cncnc3)c2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:9]:[#7;a:8]:[c:7]1:[c:5](:[c:6]):[c;H0;D3;+0:4](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[c:13]:[#7;a:14... | null | [] | null | null | null | null | The title compound, MS: m/e=389.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 5-pyrimidineboronic acid and 2-amino-4-(trifluoromethyl)thiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1cncnc1 | c1cncnc1.c1cnc2cnccc2c1 | c1cncnc1.c1cnc2cnccc2c1.c1cscn1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1nc(C(F)(F)F)cs1.OB(O)c1cncnc1>>Cc1ccc2c(-c3cncnc3)cnc(Nc3nc(C(F)(F)F)cs3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-23e706a96f3a4716881141931693c60c | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1nc(Cl)cs1.OB(O)c1cncnc1>>Cc1ccc2c(-c3cncnc3)cnc(Nc3nc(Cl)cs3)c2n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.N1=CN=CC(=C1)B(O)O.NC=1SC=C(N1)Cl>>ClC=1N=C(SC1)NC=1N=CC(=C2C=CC(=NC12)C)C=1C=NC=NC1 | Cl[c:15]1[n:14][cH:13][c:6](I)[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:24][c:23]21.[NH2:16][c:17]1[n:18][c:19]([Cl:20])[cH:21][s:22]1.OB(O)[c:7]1[cH:8][n:9][cH:10][n:11][cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][n:9][cH:10][n:11][cH:12]3)[cH:13][n:14][c:15]([NH:16][c:17]3[n:18][c:19]([Cl:20])[cH:21][s:22]3)... | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1nc(Cl)cs1.OB(O)c1cncnc1 | Cc1ccc2c(-c3cncnc3)cnc(Nc3nc(Cl)cs3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4244081fc93cf0015a20104762a30e11c662ef9f6f0a107f9d9916fab9b5c60d | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3nccs3)ncc(-c3cncnc3)c2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:9]:[#7;a:8]:[c:7]1:[c:5](:[c:6]):[c;H0;D3;+0:4](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[c:13]:[#7;a:14... | null | [] | null | null | null | null | The title compound, MS: m/e=354.9 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 5-pyrimidineboronic acid and 2-amino-4-chlorothiazole (Example K).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1cncnc1 | c1cncnc1.c1cnc2cnccc2c1 | c1cncnc1.c1cnc2cnccc2c1.c1cscn1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1nc(Cl)cs1.OB(O)c1cncnc1>>Cc1ccc2c(-c3cncnc3)cnc(Nc3nc(Cl)cs3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e6b8d0055844665bae77ba5f661a749 | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1cncc(F)c1>>Cc1csc(Nc2ncc(-c3cncc(F)c3)c3ccc(C)nc23)n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.FC=1C=NC=C(C1)B(O)O.NC=1SC=C(N1)C>>FC=1C=C(C=NC1)C1=C2C=CC(=NC2=C(N=C1)NC=1SC=C(N1)C)C | Cl[c:7]1[n:8][cH:9][c:10](I)[c:18]2[cH:19][cH:20][c:21]([CH3:22])[n:23][c:24]12.[CH3:1][c:2]1[cH:3][s:4][c:5]([NH2:6])[n:25]1.OB(O)[c:11]1[cH:12][n:13][cH:14][c:15]([F:16])[cH:17]1>>[CH3:1][c:2]1[cH:3][s:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10](-[c:11]3[cH:12][n:13][cH:14][c:15]([F:16])[cH:17]3)[c:18]3[cH:19][cH:20][c:21]... | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1cncc(F)c1 | Cc1csc(Nc2ncc(-c3cncc(F)c3)c3ccc(C)nc23)n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3nccs3)c3ncccc23)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:6]:[c:5]1:[c:7](:[#7;a:8]:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:16]-[c:17]2:[#16;a:18]:[c:19]:[c:20]:[#7;a... | null | [] | null | null | null | null | The title compound, MS: m/e=352.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 3-fluoro-5-pyridineboronic acid and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1cscn1.c1ccncc1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1.OB(O)c1cncc(F)c1>>Cc1csc(Nc2ncc(-c3cncc(F)c3)c3ccc(C)nc23)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8993cc82e4144605b5916d2099387376 | Cc1ccc(B(O)O)cn1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1>>Cc1ccc(-c2cnc(Nc3nc(C)cs3)c3nc(C)ccc23)cn1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.O.CC1=NC=C(C=C1)B(O)O.NC=1SC=C(N1)C>>CC1=NC2=C(N=CC(=C2C=C1)C=1C=NC(=CC1)C)NC=1SC=C(N1)C | OB(O)[c:5]1[cH:4][cH:3][c:2]([CH3:1])[n:25][cH:24]1.Cl[c:9]1[n:8][cH:7][c:6](I)[c:23]2[c:17]1[n:18][c:19]([CH3:20])[cH:21][cH:22]2.[NH2:10][c:11]1[n:12][c:13]([CH3:14])[cH:15][s:16]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]([NH:10][c:11]3[n:12][c:13]([CH3:14])[cH:15][s:16]3)[c:17]3[n:18][c:19]([CH3:20])[... | Cc1ccc(B(O)O)cn1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1 | Cc1ccc(-c2cnc(Nc3nc(C)cs3)c3nc(C)ccc23)cn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3nccs3)c3ncccc23)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]:[c:20]:[#7;a:21]:1>>[c:9]:[#7;a:8]:[c:7]1:[c:5](:[c:6]):[c;H0;D3;+0:4](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:1... | null | [] | null | null | null | null | The title compound, MS: m/e=348.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 2-methylpyridine-5-boronic acid hydrate and 2-amino-4-methylthiazole.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1ccncc1.c1cnc2cnccc2c1 | c1ccncc1.c1cnc2cnccc2c1 | c1ccncc1.c1cscn1.c1cnc2cnccc2c1 | HCl.I-.B | null | null | null | Cc1ccc(B(O)O)cn1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1csc(N)n1>>Cc1ccc(-c2cnc(Nc3nc(C)cs3)c3nc(C)ccc23)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-407b982ab82d4e89bd0a11c419fd97bf | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nccc(N)n1.OB(O)c1cncnc1>>Cc1ccc2c(-c3cncnc3)cnc(Nc3ccnc(C)n3)c2n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.N1=CN=CC(=C1)B(O)O.NC1=NC(=NC=C1)C>>CC1=NC=CC(=N1)NC=1N=CC(=C2C=CC(=NC12)C)C=1C=NC=NC1 | Cl[c:15]1[n:14][cH:13][c:6](I)[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:25][c:24]21.[NH2:16][c:17]1[cH:18][cH:19][n:20][c:21]([CH3:22])[n:23]1.OB(O)[c:7]1[cH:8][n:9][cH:10][n:11][cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][n:9][cH:10][n:11][cH:12]3)[cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][cH:19][n:20][c:21]([... | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nccc(N)n1.OB(O)c1cncnc1 | Cc1ccc2c(-c3cncnc3)cnc(Nc3ccnc(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4244081fc93cf0015a20104762a30e11c662ef9f6f0a107f9d9916fab9b5c60d | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3ccncn3)ncc(-c3cncnc3)c2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[#7;a:18]:[c:19]:[#7;a:20]:[c:21]:[c:22]:1>>[c:9]:[#7;a:8]:[c:7]1:[c:5](:[c:6]):[c;H0;D3;+0:4](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[c:13]:[#... | null | [] | null | null | null | null | The title compound, MS: m/e=330.1 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 5-pyrimidineboronic acid and 4-amino-2-methylpyrimidine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1cncnc1 | c1cncnc1.c1cnc2cnccc2c1 | c1cncnc1.c1cnc2cnccc2c1.c1cncnc1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nccc(N)n1.OB(O)c1cncnc1>>Cc1ccc2c(-c3cncnc3)cnc(Nc3ccnc(C)n3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7cdf3b2fa08a47c484b424cf51e87071 | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1ccnc(Cl)c1.OB(O)c1cncnc1>>Cc1ccc2c(-c3cncnc3)cnc(Nc3ccnc(Cl)c3)c2n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.N1=CN=CC(=C1)B(O)O.NC1=CC(=NC=C1)Cl>>ClC1=NC=CC(=C1)NC=1N=CC(=C2C=CC(=NC12)C)C=1C=NC=NC1 | Cl[c:15]1[n:14][cH:13][c:6](I)[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:25][c:24]21.[NH2:16][c:17]1[cH:18][cH:19][n:20][c:21]([Cl:22])[cH:23]1.OB(O)[c:7]1[cH:8][n:9][cH:10][n:11][cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][n:9][cH:10][n:11][cH:12]3)[cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][cH:19][n:20][c:21]([... | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1ccnc(Cl)c1.OB(O)c1cncnc1 | Cc1ccc2c(-c3cncnc3)cnc(Nc3ccnc(Cl)c3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4244081fc93cf0015a20104762a30e11c662ef9f6f0a107f9d9916fab9b5c60d | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3ccncc3)ncc(-c3cncnc3)c2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:1.[NH2;D1;+0:16]-[c:17]1:[c:18]:[c:19]:[#7;a:20]:[c:21]:[c:22]:1>>[c:9]:[#7;a:8]:[c:7]1:[c:5](:[c:6]):[c;H0;D3;+0:4](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[c:13]:[#7;a... | null | [] | null | null | null | null | The title compound, MS: m/e=349.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 5-pyrimidineboronic acid and 4-amino-2-chloropyridine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1cncnc1 | c1cncnc1.c1cnc2cnccc2c1 | c1cncnc1.c1cnc2cnccc2c1.c1ccncc1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Nc1ccnc(Cl)c1.OB(O)c1cncnc1>>Cc1ccc2c(-c3cncnc3)cnc(Nc3ccnc(Cl)c3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c6e12f66ffa48a48b47d319f6b6d44a | Cc1cc(B(O)O)n(C)n1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nc(N)cs1>>Cc1ccc2c(-c3cc(C)nn3C)cnc(Nc3csc(C)n3)c2n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.CN1N=C(C=C1B(O)O)C.NC=1N=C(SC1)C>>CN1N=C(C=C1C1=C2C=CC(=NC2=C(N=C1)NC=1N=C(SC1)C)C)C | OB(O)[c:7]1[cH:8][c:9]([CH3:10])[n:11][n:12]1[CH3:13].Cl[c:16]1[n:15][cH:14][c:6](I)[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:25][c:24]21.[NH2:17][c:18]1[cH:19][s:20][c:21]([CH3:22])[n:23]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][c:9]([CH3:10])[n:11][n:12]3[CH3:13])[cH:14][n:15][c:16]([NH:17][c:18]3[cH:19][s:20][c... | Cc1cc(B(O)O)n(C)n1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nc(N)cs1 | Cc1ccc2c(-c3cc(C)nn3C)cnc(Nc3csc(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1db5ab63aab22f28a1b1f0861587bde4bafc83e5a9b1180b7d2ddfbaedff9645 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3cscn3)ncc(-c3ccn[nH]3)c2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[c:12](-[C;D1;H3:13]):[#7;a:14]:[#7;a:15]:1-[C;D1;H3:16].[NH2;D1;+0:17]-[c:18]1:[#7;a:19]:[c:20]:[#16;a:21]:[c:22]:1>>[C;D1;H3:13]-[c:12]1:[#7;a:14]:[#7;a:15](-[C;D1;H3:16]):[c;H0;D3;+0:10](-[c;H0;D... | null | [] | null | null | null | null | The title compound, MS: m/e=351.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 1,3-dimethyl-1H-pyrazole-5-boronic acid (Example J) and 4-amino-2-methylthiazole (Example F).
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cc[nH]n1.c1cnc2cnccc2c1 | c1cc[nH]n1.c1cnc2cnccc2c1 | c1cc[nH]n1.c1cnc2cnccc2c1.c1cscn1 | HCl.I-.B | null | null | null | Cc1cc(B(O)O)n(C)n1.Cc1ccc2c(I)cnc(Cl)c2n1.Cc1nc(N)cs1>>Cc1ccc2c(-c3cc(C)nn3C)cnc(Nc3csc(C)n3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-32ab1c5b600542efb525eba78db2cc1a | Brc1ncccn1.Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1>>Cc1ccc2c(-c3ncccn3)cnc(Nc3csc(C)n3)c2n1 | ClC1=NC=C(C=2C=CC(=NC12)C)B(O)O.BrC1=NC=CC=N1.NC=1N=C(SC1)C>>CC1=NC2=C(N=CC(=C2C=C1)C1=NC=CC=N1)NC=1N=C(SC1)C | Br[c:7]1[n:8][cH:9][cH:10][cH:11][n:12]1.OB(O)[c:6]1[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:24][c:23]2[c:15](Cl)[n:14][cH:13]1.[NH2:16][c:17]1[cH:18][s:19][c:20]([CH3:21])[n:22]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[n:8][cH:9][cH:10][cH:11][n:12]3)[cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][s:19][c:20]([CH3:21])[n:22... | Brc1ncccn1.Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1 | Cc1ccc2c(-c3ncccn3)cnc(Nc3csc(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4244081fc93cf0015a20104762a30e11c662ef9f6f0a107f9d9916fab9b5c60d | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc(-c2cnc(Nc3cscn3)c3ncccc23)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8]:[c;H0;D3;+0:9](-B(-O)-O):[c:10](:[c:11]):[c:12]:1:[#7;a:13]:[c:14].[NH2;D1;+0:15]-[c:16]1:[#7;a:17]:[c:18]:[#16;a:19]:[c:20]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[c:8]:[#7;a:7]:[c;H0;D3;+0:6](-[NH;D2;+0:15]-[c:16]2:[#7;a:17... | null | [] | null | null | null | null | The title compound, MS: m/e=335.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-2-methyl-[1,7]naphthyridine-5-boronic acid (Example L), 2-bromopyrimidine and 4-amino-2-methylthiazole (Example F).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cncnc1.c1cnc2cnccc2c1 | c1cncnc1.c1cnc2cnccc2c1 | c1cncnc1.c1cnc2cnccc2c1.c1cscn1 | HCl.Br-.B | null | null | null | Brc1ncccn1.Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1>>Cc1ccc2c(-c3ncccn3)cnc(Nc3csc(C)n3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9dd1e635fbf5408eb7ddd21c248694de | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1.Cc1ncccc1Br>>Cc1ccc2c(-c3cccnc3C)cnc(Nc3csc(C)n3)c2n1 | ClC1=NC=C(C=2C=CC(=NC12)C)B(O)O.BrC=1C(=NC=CC1)C.NC=1N=C(SC1)C>>CC1=NC2=C(N=CC(=C2C=C1)C=1C(=NC=CC1)C)NC=1N=C(SC1)C | OB(O)[c:6]1[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:25][c:24]2[c:16](Cl)[n:15][cH:14]1.[NH2:17][c:18]1[cH:19][s:20][c:21]([CH3:22])[n:23]1.Br[c:7]1[cH:8][cH:9][cH:10][n:11][c:12]1[CH3:13]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][cH:9][cH:10][n:11][c:12]3[CH3:13])[cH:14][n:15][c:16]([NH:17][c:18]3[cH:19][s:20][c:21... | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1.Cc1ncccc1Br | Cc1ccc2c(-c3cccnc3C)cnc(Nc3csc(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 733370bfba1413f005d5574e2bd5ddcfddd1ba1c1ffa1172462b21d0628ee7e3 | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cncc(-c2cnc(Nc3cscn3)c3ncccc23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C;D1;H3:7].Cl-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10]:[c;H0;D3;+0:11](-B(-O)-O):[c:12](:[c:13]):[c:14]:1:[#7;a:15]:[c:16].[NH2;D1;+0:17]-[c:18]1:[#7;a:19]:[c:20]:[#16;a:21]:[c:22]:1>>[C;D1;H3:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:11]1:[c:10]:[#7... | null | [] | null | null | null | null | The title compound, MS: m/e=348.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-2-methyl-[1,7]naphthyridine-5-boronic acid (Example L), 3-bromo-2-methylpyridine and 4-amino-2-methylthiazole (Example F).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1ccncc1 | c1ccncc1.c1cnc2cnccc2c1 | c1ccncc1.c1cnc2cnccc2c1.c1cscn1 | HCl.Br-.B | null | null | null | Cc1ccc2c(B(O)O)cnc(Cl)c2n1.Cc1nc(N)cs1.Cc1ncccc1Br>>Cc1ccc2c(-c3cccnc3C)cnc(Nc3csc(C)n3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee2265af486a4d7984bae24e67a5347b | Cc1ccc2c(I)cnc(Cl)c2n1.Cn1ccc(N)n1.OB(O)c1cncnc1>>Cc1ccc2c(-c3cncnc3)cnc(Nc3ccn(C)n3)c2n1 | ClC=1N=CC(=C2C=CC(=NC12)C)I.N1=CN=CC(=C1)B(O)O.CN1N=C(C=C1)N>>CN1N=C(C=C1)NC=1N=CC(=C2C=CC(=NC12)C)C=1C=NC=NC1 | Cl[c:15]1[n:14][cH:13][c:6](I)[c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:24][c:23]21.[NH2:16][c:17]1[cH:18][cH:19][n:20]([CH3:21])[n:22]1.OB(O)[c:7]1[cH:8][n:9][cH:10][n:11][cH:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6](-[c:7]3[cH:8][n:9][cH:10][n:11][cH:12]3)[cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][cH:19][n:20]([CH3:21])[n:2... | Cc1ccc2c(I)cnc(Cl)c2n1.Cn1ccc(N)n1.OB(O)c1cncnc1 | Cc1ccc2c(-c3cncnc3)cnc(Nc3ccn(C)n3)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4244081fc93cf0015a20104762a30e11c662ef9f6f0a107f9d9916fab9b5c60d | 9727d519db9255a29f71e4ae6f86c9b68430035908d967236e60291d0748e38a | c1cnc2c(Nc3cc[nH]n3)ncc(-c3cncnc3)c2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c;H0;D3;+0:4](-I):[c:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].O-B(-O)-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[#7;a:14]:[c:15]:1.[C;D1;H3:16]-[#7;a:17]1:[#7;a:18]:[c:19](-[NH2;D1;+0:20]):[c:21]:[c:22]:1>>[C;D1;H3:16]-[#7;a:17]1:[#7;a:18]:[c:19](-[NH;D2;+0:20]-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:... | null | [] | null | null | null | null | The title compound, MS: m/e=318.2 (M+H+), was prepared in accordance with the general method of example 15 step 1 and step 3 from 8-chloro-5-iodo-2-methyl-[1,7]naphthyridine (Example I), 5-pyrimidineboronic acid and 1-methyl-1H-pyrazol-3-ylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Boronic acid | Secondary amine | c1cnc2cnccc2c1.c1cncnc1 | c1cncnc1.c1cnc2cnccc2c1 | c1cncnc1.c1cnc2cnccc2c1.c1cc[nH]n1 | HCl.I-.B | null | null | null | Cc1ccc2c(I)cnc(Cl)c2n1.Cn1ccc(N)n1.OB(O)c1cncnc1>>Cc1ccc2c(-c3cncnc3)cnc(Nc3ccn(C)n3)c2n1 |
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