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-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1239a307ee3d4a5296ffa6fb6b34bcfc | COC(=O)C#CC(=O)OC.COC(=O)c1c(N)cccc1OC>>COC(=O)c1nc2cccc(OC)c2c(O)c1C(=O)OC | NC1=C(C(=O)OC)C(=CC=C1)OC.C(#CC(=O)OC)C(=O)OC.CC(C)([O-])C.[K+]>>OC1=C(C(=NC2=CC=CC(=C12)OC)C(=O)OC)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[C:5]#[C:17][C:18](=[O:19])[O:20][CH3:21].CO[C:15]([c:14]1[c:7]([NH2:6])[cH:8][cH:9][cH:10][c:11]1[O:12][CH3:13])=[O:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]2[cH:8][cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]2[c:15]([OH:16])[c:17]1[C:18](=[O:19])[O:20][CH3:21] | COC(=O)C#CC(=O)OC.COC(=O)c1c(N)cccc1OC | COC(=O)c1nc2cccc(OC)c2c(O)c1C(=O)OC | null | null | C(C)(C)(C)O | Aromatic Heterocycle Formation | OtherReaction | f5368757c96521e83619cf21dfc52b28c31825e0516659832aaa47488ac6716c | bbcf1c85e1dbdba58f5fefc8b60992ba8e370d006abd0aa7780d40fd3f3dc3a2 | c1ccc2ncccc2c1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7].[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C;H0;D2;+0:12]#[C;H0;D2;+0:13]-[C:14](=[O;D1;H0:15])-[#8:16]-[C;D1;H3:17]>>[C;D1;H3:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[c;H0;D3;+0:12]1:[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3](:[c:4]):[c;H0;D3;+0:1](-[OH;D1;+... | 65 | [{"value": 65.0, "product": "OC1=C(C(=NC2=CC=CC(=C12)OC)C(=O)OC)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of methyl 2-amino-6-methoxybenzoate ((1.30 g, 7.17 mM) and dimethyl acetylenedicarboxylate (1.17 g, 8.23 mM) in t-butanol (11 mL) was refluxed under a nitrogen atmosphere for 4 hr. The reaction mixture was cooled to room temperature, potassium t-butoxide (0.92 g, 8.23 mM) was added, and the resulting mixture... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Primary amine | Ester.Ester.Aromatic alcohol | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | C(C)(C)(C)O | null | null | COC(=O)C#CC(=O)OC.COC(=O)c1c(N)cccc1OC>C(C)(C)(C)O>COC(=O)c1nc2cccc(OC)c2c(O)c1C(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e1f559619b474a8e8ddc858df147e65a | COC(=O)c1nc2cc(Cl)ccc2c(Cl)c1C(=O)OC>>COC(=O)c1cc2ccc(Cl)cc2nc1C(=O)OC | ClC1=C(C(=NC2=CC(=CC=C12)Cl)C(=O)OC)C(=O)OC.C(=O)[O-].[Na+].O>>ClC1=CC=C2C=C(C(=NC2=C1)C(=O)OC)C(=O)OC | Cl[c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:15]([C:16](=[O:17])[O:18][CH3:19])[n:14][c:13]2[c:7]1[cH:8][cH:9][c:10]([Cl:11])[cH:12]2>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]2[n:14][c:15]1[C:16](=[O:17])[O:18][CH3:19] | COC(=O)c1nc2cc(Cl)ccc2c(Cl)c1C(=O)OC | COC(=O)c1cc2ccc(Cl)cc2nc1C(=O)OC | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CN(C=O)C | Functional Group Interconversion | Aromatic dehalogenation | 9d8b09641537c9b7067a6060cf65ecd110c7af466a7b229ce3601533f966554e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6]):[c:7](-[C:8](-[#8:9])=[O;D1;H0:10]):[#7;a:11]:[c:12](:[c:13]):[c:14]:1:[c:15]>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#7;a:11]:[c:12](:[c:13]):[c:14](:[c:15]):[cH;D2;+0:1]:[c:2]:1-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6] | 134.8 | [{"value": 134.8, "product": "ClC1=CC=C2C=C(C(=NC2=C1)C(=O)OC)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of dimethyl 4,7-dichloroquinoline-2,3-dicarboxylate (5.00 g, 15.9 mM), sodium formate (1.63 g, 23.9 mM) and tetrakis(triphenylphosphine)palladium(0) (0.92 g, 0.80 mM) in anhydrous dimethylformamide (75 mL) under a nitrogen atmosphere was heated at 90°-95° C. for 7 hr. No reaction occurred so the react... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | Other | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C=O)C | null | null | COC(=O)c1nc2cc(Cl)ccc2c(Cl)c1C(=O)OC>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C=O)C>COC(=O)c1cc2ccc(Cl)cc2nc1C(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-454fe2e70f3f4c0c89014e75840e632f | COC(=O)c1nc2ccccc2c(N)c1C(=O)OC.NN>>Nc1c2ccccc2nc2c(=O)[nH][nH]c(=O)c12 | NC1=C(C(=NC2=CC=CC=C12)C(=O)OC)C(=O)OC.O.NN>>NC1=C2C(=NC=3C=CC=CC13)C(NNC2=O)=O | CO[C:11]([c:10]1[n:9][c:8]2[c:3]([c:2]([NH2:1])[c:17]1[C:15](OC)=[O:16])[cH:4][cH:5][cH:6][cH:7]2)=[O:12].[NH2:13][NH2:14]>>[NH2:1][c:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[n:9][c:10]2[c:11](=[O:12])[nH:13][nH:14][c:15](=[O:16])[c:17]12 | COC(=O)c1nc2ccccc2c(N)c1C(=O)OC.NN | Nc1c2ccccc2nc2c(=O)[nH][nH]c(=O)c12 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | ec1917a0188259fb1d502a40ed3d9aad8b3b567f28677d868775be5ee838e719 | 1775b7eba35fc46eaa0b0ad39cde9e207db465168e4fe5d9832db816e257be74 | O=c1[nH][nH]c(=O)c2nc3ccccc3cc12 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[#7;a:4]:[c:5]):[c:6](-[C;H0;D3;+0:7](=[O;D1;H0:8])-O-C):[c:9].[NH2;D1;+0:10]-[NH2;D1;+0:11]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:10]:[nH;D2;+0:11]:[c;H0;D3;+0:7](=[O;D1;H0:8]):[c:6](:[c:9]):[c:3]:1:[#7;a:4]:[c:5] | 98.8 | [{"value": 68.0, "product": "NC1=C2C(=NC=3C=CC=CC13)C(NNC2=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.8, "product": "NC1=C2C(=NC=3C=CC=CC13)C(NNC2=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of dimethyl 4-aminoquinoline-2,3-dicarboxylate (0.15 g, 0.58 mM) in ethanol (4 mL) was added hydrazine hydrate (1.46 g, 29.2 mM) and the resulting solution was refluxed for 3 hr. The reaction mixture was cooled to room temperature and filtered to separate the yellow precipitate (0.12 g). This mate... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester.Ester | null | c1ccc2ncccc2c1 | C1=c2cc3ccccc3nc2=CNN1 | C1=c2cc3ccccc3nc2=CNN1 | HO- | C(C)O | null | null | COC(=O)c1nc2ccccc2c(N)c1C(=O)OC.NN>C(C)O>Nc1c2ccccc2nc2c(=O)[nH][nH]c(=O)c12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-07ccba316ab64ff1a0c5fdbf401e073f | COC(=O)C#CC(=O)OC.N#Cc1ccccc1N>>COC(=O)/C=C(\Nc1ccccc1C#N)C(=O)OC | NC1=C(C#N)C=CC=C1.C(#CC(=O)OC)C(=O)OC>>C(#N)C1=C(N/C(/C(=O)OC)=C\C(=O)OC)C=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[C:5]#[C:6][C:16](=[O:17])[O:18][CH3:19].[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[C:14]#[N:15]>>[CH3:1][O:2][C:3](=[O:4])/[CH:5]=[C:6](\[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[C:14]#[N:15])[C:16](=[O:17])[O:18][CH3:19] | COC(=O)C#CC(=O)OC.N#Cc1ccccc1N | COC(=O)/C=C(\Nc1ccccc1C#N)C(=O)OC | null | null | C(C)(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 3d5adf24dd93857513fe82642f7d3d4feab92a8bf952edd7458e6f077b54016e | cb45d3f2664ea1c07edca6192a95c91d6c98f4c61196cc5a896d41447e7a94b5 | c1ccccc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D2;+0:5]#[C;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])/[C;H0;D3;+0:5](=[CH;D2;+0:6]/[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10])-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14] | 44.3 | [{"value": 44.3, "product": "C(#N)C1=C(N/C(/C(=O)OC)=C\\C(=O)OC)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-aminobenzonitrile (5.00 g, 42.3 mM) and dimethyl acetylenedicarboxylate (6.42 g, 45.2 mM) in t-butanol (70.5 mL) was refluxed under a nitrogen atmosphere for 12 hr. After cooling the reaction mixture to room temperature, a precipitate formed and was collected by filtration. The material was washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Enamine | null | null | c1ccccc1 | null | C(C)(C)(C)O | null | null | COC(=O)C#CC(=O)OC.N#Cc1ccccc1N>C(C)(C)(C)O>COC(=O)/C=C(\Nc1ccccc1C#N)C(=O)OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-57ce19bea6534a878ad8a04143464a6c | O.O=C1Nc2cc(I)ccc2C1=O>>O=c1[nH]c2cc(I)ccc2c(=O)o1 | IC1=CC=C2C(C(NC2=C1)=O)=O.O>>IC1=CC2=C(C(OC(N2)=O)=O)C=C1 | [OH2:13].[O:1]=[C:2]1[NH:3][c:4]2[cH:5][c:6]([I:7])[cH:8][cH:9][c:10]2[C:11]1=[O:12]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([I:7])[cH:8][cH:9][c:10]2[c:11](=[O:12])[o:13]1 | O.O=C1Nc2cc(I)ccc2C1=O | O=c1[nH]c2cc(I)ccc2c(=O)o1 | null | [O-2].[O-2].[O-2].[Cr+6] | C(C)(=O)O.C(C)(=O)OC(C)=O | Miscellaneous | OtherReaction | 5d9736fd05de108b71c591acfae61cb6af4635bfbe20446a56c7b74a3d5953af | 8242b1e5e71ebd9e44538af93284e3a1145dd4183387fabf58d37d4a04b884a5 | O=c1[nH]c2ccccc2c(=O)o1 | [O;D1;H0:1]=[C;H0;D3;+0:2]1-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]-1:[c:9].[OH2;D0;+0:10]>>[O;D1;H0:1]=[c;H0;D3;+0:2]1:[o;H0;D2;+0:10]:[c;H0;D3;+0:3](=[O;D1;H0:4]):[nH;D2;+0:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 81.8 | [{"value": 81.8, "product": "IC1=CC2=C(C(OC(N2)=O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a stirred warm (80° C.) solution of 6-iodo-1H-indole-2,3-dione (3.0 g, 11 mM) in acetic acid (10 mL) and acetic anhydride (10 mL) was added in small portions chromium trioxide (1.83 g, 18.3 mM) while maintaining the temperature of the reaction mixture at 80°-90° C. The reaction mixture was then heated at 80° C. for ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amide | null | c1ccc2c(c1)CCN2 | c1ccc2cocnc2c1 | c1ccc2cocnc2c1 | null | [O-2].[O-2].[O-2].[Cr+6].C(C)(=O)O.C(C)(=O)OC(C)=O | 80 | null | O.O=C1Nc2cc(I)ccc2C1=O>[O-2].[O-2].[O-2].[Cr+6].C(C)(=O)O.C(C)(=O)OC(C)=O>O=c1[nH]c2cc(I)ccc2c(=O)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c4712f788bc44516bf8778e183920013 | O=c1[nH]c2cc(I)ccc2c(=O)o1>>COC(=O)c1ccc(I)cc1N | O.[OH-].[Na+].IC1=CC2=C(C(OC(N2)=O)=O)C=C1>>NC1=C(C(=O)OC)C=CC(=C1)I | O=[c:1]1[o:2][c:3](=[O:4])[c:5]2[cH:6][cH:7][c:8]([I:9])[cH:10][c:11]2[nH:12]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([I:9])[cH:10][c:11]1[NH2:12] | O=c1[nH]c2cc(I)ccc2c(=O)o1 | COC(=O)c1ccc(I)cc1N | null | null | CO | Reduction | OtherReaction | fb3a8999d982d1c42a150fbbeb96fa0db2838a9c48a5140f183de4d3421c8ad6 | 9f87be38aa9793f80b3cef223629015a04ccba30a9633b313486e0a6edc9c43d | c1ccccc1 | O=[c;H0;D3;+0:1]1:[nH;D2;+0:2]:[c:3](:[c:4]):[c:5](:[c:6]):[c;H0;D3;+0:7](=[O;D1;H0:8]):[o;H0;D2;+0:9]:1>>[CH3;D1;+0:1]-[O;H0;D2;+0:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:5](:[c:6]):[c:3](-[NH2;D1;+0:2]):[c:4] | 80.2 | [{"value": 80.0, "product": "NC1=C(C(=O)OC)C=CC(=C1)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.2, "product": "NC1=C(C(=O)OC)C=CC(=C1)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a stirred solution of sodium hydroxide (0.048 g, 1.2 mM) in methanol (4.5 mL) was added 7-iodo-2H-3,1-benzoxazine-2,4(1H)-dione (2.6 g, 9.0 mM). The mixture was heated at 60° C. for 7 hr and the resulting solution was cooled, poured into water and extracted with ethyl acetate. The combined extracts were washed once ... | 10.6084/m9.figshare.5104873.v1 | null | null | Ester.Primary amine | c1ccc2cocnc2c1 | c1ccccc1 | c1ccccc1 | Other | CO | 60 | null | O=c1[nH]c2cc(I)ccc2c(=O)o1>CO>COC(=O)c1ccc(I)cc1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ec04a768a81546c687358bb4525e5d24 | CCOC(=O)CC(=O)C(=O)OCC.O=c1[nH]c2cc(Br)ccc2c(=O)o1>>CCOC(=O)c1nc2cc(Br)ccc2c(O)c1C(=O)OCC | [Na].O=C(C(=O)OCC)CC(=O)OCC.BrC1=CC2=C(C(OC(N2)=O)=O)C=C1>>BrC1=CC=C2C(=C(C(=NC2=C1)C(=O)OCC)C(=O)OCC)O | O=[C:17]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:18](=[O:19])[O:20][CH2:21][CH3:22].O=c1[nH:7][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]2[c:15](=O)[o:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]2[cH:9][c:10]([Br:11])[cH:12][cH:13][c:14]2[c:15]([OH:16])[c:17]1[C:18](=[O:19])[O:20][CH2:21][CH3:22] | CCOC(=O)CC(=O)C(=O)OCC.O=c1[nH]c2cc(Br)ccc2c(=O)o1 | CCOC(=O)c1nc2cc(Br)ccc2c(O)c1C(=O)OCC | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 6a57a3597d32a89058ecee7d5f10c7dfe66b566f5458c9a02f9ca35e0d21a60d | 9da8ba30ba25142ceb94d865cd4c0f29929d07b92e6a842861f67100ed84de1c | c1ccc2ncccc2c1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10].O=[c;H0;D3;+0:11]1:[o;H0;D2;+0:12]:c(=O):[nH;D2;+0:13]:[c:14](:[c:15]):[c:16]:1:[c:17]>>[C:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[c;H0;D3;+0:1]1:[c;H0;D3;+0:11](-[OH;D1;+0:12]):[c:16](:[c:17]):[c:14](:[c:15]):[n;H0;D2;+0:13]:[c... | 24 | [{"value": 24.0, "product": "BrC1=CC=C2C(=C(C(=NC2=C1)C(=O)OCC)C(=O)OCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.7, "product": "BrC1=CC=C2C(=C(C(=NC2=C1)C(=O)OCC)C(=O)OCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | null | null | To a stirred mixture of diethyl oxosuccinate sodium salt (1.31 g, 6.23 mM) in dimethylformamide (DMF, 15 mL) under a nitrogen atmosphere was added a solution of 7-bromo-2H-3,1-benzoxazine-2,4(1H)-dione (1.50 g, 6.20 mM) in DMF (15 mL). The resulting reaction mixture was heated to 130° C. over 2.5 hr and then refluxed f... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ester | Ester.Ester.Aromatic alcohol | c1ccc2cocnc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | CN(C=O)C | 130 | null | CCOC(=O)CC(=O)C(=O)OCC.O=c1[nH]c2cc(Br)ccc2c(=O)o1>CN(C=O)C>CCOC(=O)c1nc2cc(Br)ccc2c(O)c1C(=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4afa85f5bd694c988e0706bc73077ac1 | O=C(Cl)CCc1ccccc1.O=c1[nH][nH]c(=O)c2c(O)c3ccc(Cl)cc3nc12>>O=C(CCc1ccccc1)Oc1n[nH]c(=O)c2nc3cc(Cl)ccc3c(O)c12 | ClC=1C=CC=2C(=C3C(=NC2C1)C(NNC3=O)=O)O.C(CCC1=CC=CC=C1)(=O)Cl>>ClC=1C=CC=2C(=C3C(=NC2C1)C(NN=C3OC(CCC3=CC=CC=C3)=O)=O)O | Cl[C:2](=[O:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[O:11]=[c:12]1[nH:13][nH:14][c:15](=[O:16])[c:17]2[n:18][c:19]3[cH:20][c:21]([Cl:22])[cH:23][cH:24][c:25]3[c:26]([OH:27])[c:28]12>>[O:1]=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[O:11][c:12]1[n:13][nH:14][c:15](=[O:16])[c:17]2[n:18][c... | O=C(Cl)CCc1ccccc1.O=c1[nH][nH]c(=O)c2c(O)c3ccc(Cl)cc3nc12 | O=C(CCc1ccccc1)Oc1n[nH]c(=O)c2nc3cc(Cl)ccc3c(O)c12 | null | null | N1=CC=CC=C1.O | Acylation | OtherReaction | b18d846ff0412004ceb2ba9c6d237268ee56f1c008c4c07cdd457eed44dc75b6 | 74160603d2471b6dce676fdb61c753a80de32635d34da1c285b2b50abd3324f9 | O=C(CCc1ccccc1)Oc1n[nH]c(=O)c2nc3ccccc3cc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[O;H0;D1;+0:5]=[c;H0;D3;+0:6]1:[nH;D2;+0:7]:[#7;a:8]:[c:9]:[c:10](:[#7;a:11]:[c:12]):[c:13]:1:[c:14]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[c:10](:[#7;a:11]:[c:12]):[c:13]:1:[c:14] | null | [] | null | null | 2 | HOUR | A mixture of 7-chloro-2,3-dihydro-10-hydroxypyridazino[4,5-b]quinoline-1,4-dione (0.60 g, 2.3 mM), as prepared in Example 2, and hydrocinnamoyl chloride (1.15 g, 6.84 mM) in pyridine (9 mL) was refluxed for 1 hr. Upon cooling to room temperature, the solution solidified. After 2 hr at room temperature, the mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ester | C1=c2cc3ccccc3nc2=CNN1 | c1ccc2cc3cnncc3nc2c1 | c1ccccc1.c1ccc2cc3cnncc3nc2c1 | HCl | N1=CC=CC=C1.O | null | 2 | O=C(Cl)CCc1ccccc1.O=c1[nH][nH]c(=O)c2c(O)c3ccc(Cl)cc3nc12>N1=CC=CC=C1.O>O=C(CCc1ccccc1)Oc1n[nH]c(=O)c2nc3cc(Cl)ccc3c(O)c12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dd94778e10ec4f848d748b205dfbec9e | CCOC(=O)CC(=O)C(=O)OCC.O=c1[nH]c2c(Cl)cccc2c(=O)o1>>CCOC(=O)c1nc2c(Cl)cccc2c(O)c1C(=O)OCC | [Na].O=C(C(=O)OCC)CC(=O)OCC.ClC1=CC=CC=2C(OC(NC21)=O)=O.O>>ClC=1C=CC=C2C(=C(C(=NC12)C(=O)OCC)C(=O)OCC)O | O=[C:17]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:18](=[O:19])[O:20][CH2:21][CH3:22].O=c1[nH:7][c:8]2[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]2[c:15](=O)[o:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]2[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]2[c:15]([OH:16])[c:17]1[C:18](=[O:19])[O:20][CH2:21][CH3:22] | CCOC(=O)CC(=O)C(=O)OCC.O=c1[nH]c2c(Cl)cccc2c(=O)o1 | CCOC(=O)c1nc2c(Cl)cccc2c(O)c1C(=O)OCC | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 2eef483005397da632942cbbc21d7e5da2fabb0c9f19f10dc593f88983716aee | 9da8ba30ba25142ceb94d865cd4c0f29929d07b92e6a842861f67100ed84de1c | c1ccc2ncccc2c1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10].O=[c;H0;D3;+0:11]1:[o;H0;D2;+0:12]:c(=O):[nH;D2;+0:13]:[c:14](:[c:15]):[c:16]:1:[c:17]>>[C:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[c;H0;D3;+0:1]1:[c;H0;D3;+0:11](-[OH;D1;+0:12]):[c:16](:[c:17]):[c:14](:[c:15]):[n;H0;D2;+0:13]:[c... | 43.8 | [{"value": 43.8, "product": "ClC=1C=CC=C2C(=C(C(=NC12)C(=O)OCC)C(=O)OCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | null | null | To a stirred mixture of diethyl oxosuccinate sodium salt (2.31 g, 11.0 mM) in dimethylformamide (20 mL) under a nitrogen atmosphere was added 8-chloro-2H-3,1-benzoxazine-2,4(1H)-dione (2.17 g, 11.0 mM). The resulting mixture was heated slowly to 130° C. and maintained at this temperature for 2.5 hr. After cooling, the ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ester | Ester.Ester.Aromatic alcohol | c1ocnc2ccccc12 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | CN(C=O)C | 130 | null | CCOC(=O)CC(=O)C(=O)OCC.O=c1[nH]c2c(Cl)cccc2c(=O)o1>CN(C=O)C>CCOC(=O)c1nc2c(Cl)cccc2c(O)c1C(=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b6d9760dfaec4627a210e1ab02e7806c | O=c1[nH]c2cccc(I)c2c(=O)o1>>COC(=O)c1c(N)cccc1I | [OH-].[Na+].IC1=CC=CC2=C1C(OC(N2)=O)=O>>NC1=C(C(=O)OC)C(=CC=C1)I | O=[c:1]1[o:2][c:3](=[O:4])[c:5]2[c:6]([nH:7]1)[cH:8][cH:9][cH:10][c:11]2[I:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:8][cH:9][cH:10][c:11]1[I:12] | O=c1[nH]c2cccc(I)c2c(=O)o1 | COC(=O)c1c(N)cccc1I | null | [OH-].[Na+] | CO | Reduction | OtherReaction | 4a877ce7f9d8b0e05ec6ae8c859c09c08e7f1fd55a56b7ca38718591b6593140 | 9f87be38aa9793f80b3cef223629015a04ccba30a9633b313486e0a6edc9c43d | c1ccccc1 | O=[c;H0;D3;+0:1]1:[nH;D2;+0:2]:[c:3](:[c:4]):[c:5](:[c:6]):[c;H0;D3;+0:7](=[O;D1;H0:8]):[o;H0;D2;+0:9]:1>>[CH3;D1;+0:1]-[O;H0;D2;+0:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:5](:[c:6]):[c:3](-[NH2;D1;+0:2]):[c:4] | 78.4 | [{"value": 78.4, "product": "NC1=C(C(=O)OC)C(=CC=C1)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.4, "product": "NC1=C(C(=O)OC)C(=CC=C1)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | To a stirred solution of sodium hydroxide (0.35 g, 8.8 mM) in methanol (31 mL) was added 5-iodo-2H-3,1-benzoxazine-2,4(1H)-dione (18.5 g, 64.0 mM). The mixture was heated at 60° C. for 1.5 hr. An additional quantitiy of sodium hydroxide (0.10 g, 2.5 mM) was added to the reaction mixture and stirring at 60° C. was conti... | 10.6084/m9.figshare.5104873.v1 | null | null | Ester.Primary amine | c1nc2ccccc2co1 | c1ccccc1 | c1ccccc1 | Other | [OH-].[Na+].CO | 60 | 1 | O=c1[nH]c2cccc(I)c2c(=O)o1>[OH-].[Na+].CO>COC(=O)c1c(N)cccc1I |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d1949a80f5a34ab9a1a505ee7b40c299 | COc1c(Cl)cc([N+](=O)[O-])cc1Cl>>COc1c(Cl)cc(N)cc1Cl | [OH-].[Na+].ClC1=C(C(=CC(=C1)[N+](=O)[O-])Cl)OC.O.O.[Sn](Cl)Cl>>ClC=1C=C(N)C=C(C1OC)Cl | O=[N+:8]([O-])[c:7]1[cH:6][c:4]([Cl:5])[c:3]([O:2][CH3:1])[c:10]([Cl:11])[cH:9]1>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([NH2:8])[cH:9][c:10]1[Cl:11] | COc1c(Cl)cc([N+](=O)[O-])cc1Cl | COc1c(Cl)cc(N)cc1Cl | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 83.7 | [{"value": 83.7, "product": "ClC=1C=C(N)C=C(C1OC)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.7, "product": "ClC=1C=C(N)C=C(C1OC)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 2,6-dichloro-4-nitroanisole (4.6 g, 21 mM) and tin(II) dichloride dihydrate (23.4 g, 104 mM) in ethanol (72 mL) was refluxed for 3 hr. After cooling to room temperature, the reaction mixture was poured into ice water which was then treated with 2N sodium hydroxide until the solution became basic. T... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | C(C)O | null | null | COc1c(Cl)cc([N+](=O)[O-])cc1Cl>C(C)O>COc1c(Cl)cc(N)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-96c9427d56a846deb08ae5a7e598c8e7 | CI.COc1c(Cl)cc(NC(=O)OC(C)(C)C)c(C(=O)O)c1Cl>>COC(=O)c1c(NC(=O)OC(C)(C)C)cc(Cl)c(OC)c1Cl | O.[H-].[Na+].C(C)(C)(C)OC(=O)NC1=C(C(=O)O)C(=C(C(=C1)Cl)OC)Cl.IC>>C(C)(C)(C)OC(=O)NC1=C(C(=O)OC)C(=C(C(=C1)Cl)OC)Cl | I[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[cH:15][c:16]([Cl:17])[c:18]([O:19][CH3:20])[c:21]1[Cl:22]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[cH:15][c:16]([Cl:17])[c:18]([O:19][CH3:20])[c:21]1[Cl:22] | CI.COc1c(Cl)cc(NC(=O)OC(C)(C)C)c(C(=O)O)c1Cl | COC(=O)c1c(NC(=O)OC(C)(C)C)cc(Cl)c(OC)c1Cl | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | c1ccccc1 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | 96 | [{"value": 96.0, "product": "C(C)(C)(C)OC(=O)NC1=C(C(=O)OC)C(=C(C(=C1)Cl)OC)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.0, "product": "C(C)(C)(C)OC(=O)NC1=C(C(=O)OC)C(=C(C(=C1)Cl)OC)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a cold (ice bath) stirred solution of 2-(tert-butoxycarbonylamino)-4,6-dichloro-5-methoxybenzoic acid (2.0 g, 5.9 mM) in 20 mL of dry dimethylformamide under a nitrogen atmosphere was added sodium hydride (0.24 g, 5.9 mM); a precipitate formed which slowly redissolved on stirring. To the resulting stirred solution w... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccccc1 | HI | CN(C=O)C | null | null | CI.COc1c(Cl)cc(NC(=O)OC(C)(C)C)c(C(=O)O)c1Cl>CN(C=O)C>COC(=O)c1c(NC(=O)OC(C)(C)C)cc(Cl)c(OC)c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8d59dafca56b4fad8c6a7600ac1e67f1 | COC(=O)c1c(NC(=O)OC(C)(C)C)cc(Cl)c(OC)c1Cl>>COC(=O)c1c(N)cc(Cl)c(OC)c1Cl | C(C)(C)(C)OC(=O)NC1=C(C(=O)OC)C(=C(C(=C1)Cl)OC)Cl.FC(C(=O)O)(F)F>>NC1=C(C(=O)OC)C(=C(C(=C1)Cl)OC)Cl | CC(C)(C)OC(=O)[NH:7][c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[c:14]([Cl:15])[c:11]([O:12][CH3:13])[c:9]([Cl:10])[cH:8]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:8][c:9]([Cl:10])[c:11]([O:12][CH3:13])[c:14]1[Cl:15] | COC(=O)c1c(NC(=O)OC(C)(C)C)cc(Cl)c(OC)c1Cl | COC(=O)c1c(N)cc(Cl)c(OC)c1Cl | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 87 | [{"value": 87.0, "product": "NC1=C(C(=O)OC)C(=C(C(=C1)Cl)OC)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution o#methyl 2-(tert-butoxycarbonylamino)-4,6-dichloro-5-methoxybenzoate (2.3 g, 6.6 mM) and trifluoroacetic acid (6.0 g, 53 mM) in methylene chloride (23 mL) was stirred at room temperature for 1.5 hr. The reaction mixture was then washed with saturated aqueous sodium bicarbonate, drie (MgSO4), filtered and con... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | C(Cl)Cl | null | null | COC(=O)c1c(NC(=O)OC(C)(C)C)cc(Cl)c(OC)c1Cl>C(Cl)Cl>COC(=O)c1c(N)cc(Cl)c(OC)c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-212e81895b584e808d5abbbb91d99bed | CCc1cc(Br)cc2c1C(=O)C(=O)N2.O=C(O)c1cccc(OO)c1C(=O)O>>CCc1cc(Br)cc2[nH]c(=O)oc(=O)c12 | O.BrC1=CC(=C2C(C(NC2=C1)=O)=O)CC.C1=CC(=C(C(=C1)OO)C(=O)O)C(=O)O>>BrC1=CC2=C(C(OC(N2)=O)=O)C(=C1)CC | [CH3:1][CH2:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]2[c:15]1[C:13](=[O:14])[C:10](=[O:11])[NH:9]2.O=C(O)c1c(OO)cccc1C(=O)[OH:12]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]2[nH:9][c:10](=[O:11])[o:12][c:13](=[O:14])[c:15]12 | CCc1cc(Br)cc2c1C(=O)C(=O)N2.O=C(O)c1cccc(OO)c1C(=O)O | CCc1cc(Br)cc2[nH]c(=O)oc(=O)c12 | null | null | C(C)(=O)O | Miscellaneous | OtherReaction | c2de0b94b09bdf803797c35375a584c41aaa053492f400c41ac8174d57dd96c3 | 23ca1a4188e84983b2834b492c533f8abb5826e748f0ff4dba158b499183ccaa | O=c1[nH]c2ccccc2c(=O)o1 | O-O-c1:c:c:c:c(-C(=O)-[OH;D1;+0:1]):c:1-C(-O)=O.[O;D1;H0:2]=[C;H0;D3;+0:3]1-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7](:[c:8])-[C;H0;D3;+0:9]-1=[O;D1;H0:10]>>[O;D1;H0:2]=[c;H0;D3;+0:3]1:[nH;D2;+0:4]:[c:5](:[c:6]):[c:7](:[c:8]):[c;H0;D3;+0:9](=[O;D1;H0:10]):[o;H0;D2;+0:1]:1 | null | [] | null | null | null | null | A stirred solution of 6-bromo-4-ethyl-1H-indole-2,3-dione (2.64 g, 10.4 mM) and the hexahydrate magnesium salt of monoperoxyphthalic acid (80% pure, 3.54 g, 5.73 mM) in glacial acetic acid (30 mL) was stirred at 60° C. for 1 hr during which time a precipitate formed. The cooled reaction mixture was then poured into col... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Ketone.Secondary amide.Peroxide | null | c1ccc2c(c1)CCN2.c1ccccc1 | c1ccc2cocnc2c1 | c1ccc2cocnc2c1 | HO- | C(C)(=O)O | null | null | CCc1cc(Br)cc2c1C(=O)C(=O)N2.O=C(O)c1cccc(OO)c1C(=O)O>C(C)(=O)O>CCc1cc(Br)cc2[nH]c(=O)oc(=O)c12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1eb43454a5ef481dbf4ca95331913c1b | CC(C)(C)OC(=O)Nc1cc(Cl)cc(C(F)(F)F)c1.O=C=O>>CC(C)(C)OC(=O)c1cc(C(F)(F)F)cc(Cl)c1C(=O)O | O.C(C)(C)(C)OC(=O)NC1=CC(=CC(=C1)C(F)(F)F)Cl.O1CCCC1.C(C)(C)(C)[Li].C(=O)=O>>C(C)(C)(C)OC(=O)C1=C(C(=O)O)C(=CC(=C1)C(F)(F)F)Cl | N([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:8]1[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][c:16]([Cl:17])[cH:18]1.[C:19](=[O:20])=[O:21]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[c:8]1[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][c:16]([Cl:17])[c:18]1[C:19](=[O:20])[OH:21] | CC(C)(C)OC(=O)Nc1cc(Cl)cc(C(F)(F)F)c1.O=C=O | CC(C)(C)OC(=O)c1cc(C(F)(F)F)cc(Cl)c1C(=O)O | null | null | CCCCC | Acylation | OtherReaction | 475bed91ea8d3dff3b5c1b6e17807dec7cd6c0c6ce79e792e8fab4b47f7eaa2f | 210646275b30fec4c694f5e99452fb6596cdedc38c8ab4483898d142267efae2 | c1ccccc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-N-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[c:12](-[Cl;D1;H0:13]):[cH;D2;+0:14]:1.[O;D1;H0:15]=[C;H0;D2;+0:16]=[O;H0;D1;+0:17]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:1... | 82 | [{"value": 82.0, "product": "C(C)(C)(C)OC(=O)C1=C(C(=O)O)C(=CC(=C1)C(F)(F)F)Cl", "details": "PERCENTYIELD", "is_desired": false}] | -75 | CELSIUS | null | null | To a cold (-100° C.) stirred solution of N-(tert-butoxycarbonyl)-3-chloro-5-trifluoromethylaniline 93.4 g, 11.5 mM) in dry tetrahydrofuran (30 mL) under a nitrogen atmosphere was added dropwise t-butyllithium (14.2 mL of 1.7 M solution, 24.2 mM) in pentane. The temperature of the reaction mixture was maintained at -103... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Carbon dioxide.Boc | Carboxylic acid.Ester.Boc | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CCCCC | -75 | null | CC(C)(C)OC(=O)Nc1cc(Cl)cc(C(F)(F)F)c1.O=C=O>CCCCC>CC(C)(C)OC(=O)c1cc(C(F)(F)F)cc(Cl)c1C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0600c001c51645919f6df926c38c5514 | Nc1cc(Cl)cc(C(F)(F)F)c1C(=O)O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>O=c1[nH]c2cc(C(F)(F)F)cc(Cl)c2c(=O)o1 | O.NC1=C(C(=O)O)C(=CC(=C1)Cl)C(F)(F)F.ClC(Cl)(Cl)OC(OC(Cl)(Cl)Cl)=O>>ClC1=CC(=CC2=C1C(OC(N2)=O)=O)C(F)(F)F | [NH2:3][c:4]1[cH:5][c:12]([Cl:13])[cH:11][c:6]([C:7]([F:8])([F:9])[F:10])[c:14]1[C:15](=[O:16])[OH:17].ClC(Cl)(Cl)O[C:2](OC(Cl)(Cl)Cl)=[O:1]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][c:12]([Cl:13])[c:14]2[c:15](=[O:16])[o:17]1 | Nc1cc(Cl)cc(C(F)(F)F)c1C(=O)O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | O=c1[nH]c2cc(C(F)(F)F)cc(Cl)c2c(=O)o1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 473d8917d142d976b6bbb3c47c54cadfe4d17a751eabb736fd7b01b50c3ead61 | 8337e7dcd80ae495bd7effbccbb483dc6496434024ea4407e426959abd54f128 | O=c1[nH]c2ccccc2c(=O)o1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[Cl;D1;H0:3]-[c;H0;D3;+0:4]1:[c:5]:[c;H0;D3;+0:6](-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[F;D1;H0:10]):[c;H0;D3;+0:11](-[C;H0;D3;+0:12](=[O;D1;H0:13])-[OH;D1;+0:14]):[c:15](-[NH2;D1;+0:16]):[cH;D2;+0:17]:1>>[Cl;D1;H0:3]-[c;H0;D3;+0:4]1:[c:5]:[c;H0;D3;+0:6](-[C:... | null | [] | null | null | 2 | HOUR | To a stirred solution of 2-amino-4-chloro-6-trifluoromethylbenzoic acid (0.53 g, 2.2 mM) in dry tetrahydrofuran (6 mL) under a nitrogen atmosphere was added bis(trichloromethyl)carbonate (0.218 g, 0.734 mM). The resulting solution was stirred at room temperature for 2 hr, poured into water and the resulting mixture ext... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Aromatic halide.Carbonic Ester.Carboxylic acid.Primary amine | Aromatic halide | c1ccccc1 | c1ccc2cocnc2c1 | c1ccc2cocnc2c1 | HCl | O1CCCC1 | null | 2 | Nc1cc(Cl)cc(C(F)(F)F)c1C(=O)O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>O1CCCC1>O=c1[nH]c2cc(C(F)(F)F)cc(Cl)c2c(=O)o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-de691adb4df542928566b3b06e2c218d | O=c1[nH]c2cc(C(F)(F)F)cc(Cl)c2c(=O)o1>>COC(=O)c1c(N)cc(C(F)(F)F)cc1Cl | C(C)OCC.[OH-].[Na+].ClC1=CC(=CC2=C1C(OC(N2)=O)=O)C(F)(F)F>>NC1=C(C(=O)OC)C(=CC(=C1)C(F)(F)F)Cl | O=[c:1]1[o:2][c:3](=[O:4])[c:5]2[c:6]([nH:7]1)[cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][c:15]2[Cl:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH2:7])[cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][c:15]1[Cl:16] | O=c1[nH]c2cc(C(F)(F)F)cc(Cl)c2c(=O)o1 | COC(=O)c1c(N)cc(C(F)(F)F)cc1Cl | null | null | CO | Reduction | OtherReaction | fb3a8999d982d1c42a150fbbeb96fa0db2838a9c48a5140f183de4d3421c8ad6 | 9f87be38aa9793f80b3cef223629015a04ccba30a9633b313486e0a6edc9c43d | c1ccccc1 | O=[c;H0;D3;+0:1]1:[nH;D2;+0:2]:[c:3](:[c:4]):[c:5](:[c:6]):[c;H0;D3;+0:7](=[O;D1;H0:8]):[o;H0;D2;+0:9]:1>>[CH3;D1;+0:1]-[O;H0;D2;+0:9]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:5](:[c:6]):[c:3](-[NH2;D1;+0:2]):[c:4] | 88 | [{"value": 88.0, "product": "NC1=C(C(=O)OC)C(=CC(=C1)C(F)(F)F)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.3, "product": "NC1=C(C(=O)OC)C(=CC(=C1)C(F)(F)F)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a stirred solution of sodium hydroxide (0.012 g, 0.31 mM) in anhydrous methanol (1.5 mL) under a nitrogen atmosphere was added 5-chloro-7-trifluoromethyl-2H-3,1-benzoxazine-2,4(1H)-dione (0.60 g, 2.3 mM). The resulting mixture was warmed to 60° C. for 0.5 hr, allowed to cool to room temperature and poured into dieth... | 10.6084/m9.figshare.5104873.v1 | null | null | Ester.Primary amine | c1ccc2cocnc2c1 | c1ccccc1 | c1ccccc1 | Other | CO | 60 | null | O=c1[nH]c2cc(C(F)(F)F)cc(Cl)c2c(=O)o1>CO>COC(=O)c1c(N)cc(C(F)(F)F)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-fb1f425ed29c488e8ffdf69649ec7433 | Nc1cc(F)ccc1C(=O)O>>COC(=O)c1ccc(F)cc1N | C([O-])(O)=O.[Na+].NC1=C(C(=O)O)C=CC(=C1)F.Cl.Cl>>NC1=C(C(=O)OC)C=CC(=C1)F | [OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[NH2:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[NH2:12] | Nc1cc(F)ccc1C(=O)O | COC(=O)c1ccc(F)cc1N | null | null | CO.O | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | c1ccccc1 | [O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[c:4]>>[C;D1;H3:5]-[O;H0;D2;+0:3]-[C:2](=[O;D1;H0:1])-[c:4] | 80.6 | [{"value": 80.6, "product": "NC1=C(C(=O)OC)C=CC(=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution of 2-amino-4-fluorobenzoic acid (4.86 g, 31.3 mM) in anhydrous methanol (100 mL) was saturated with anhydrous hydrogen chloride and then refluxed for 4 days. During the reflux period, the reaction mixture was periodically resaturated with hydrogen chloride. After the reflux period, the reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccccc1 | Other | CO.O | null | null | Nc1cc(F)ccc1C(=O)O>CO.O>COC(=O)c1ccc(F)cc1N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d22c33b8f7f941c2ae9d370668c316af | CCOC(=O)c1nc2ccc([N+](=O)[O-])cc2c(O)c1C(=O)OCC>>CCOC(=O)c1nc2ccc(N)cc2c(O)c1C(=O)OCC | OC1=C(C(=NC2=CC=C(C=C12)[N+](=O)[O-])C(=O)OCC)C(=O)OCC.C(C)(=O)O>>NC=1C=C2C(=C(C(=NC2=CC1)C(=O)OCC)C(=O)OCC)O | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[n:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:17]([C:18](=[O:19])[O:20][CH2:21][CH3:22])[c:15]([OH:16])[c:14]2[cH:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:13][c:14]2[c:15]([OH:16])[c:17]1[C:18](=[O:19])[O:20][CH2:21][CH3:22] | CCOC(=O)c1nc2ccc([N+](=O)[O-])cc2c(O)c1C(=O)OCC | CCOC(=O)c1nc2ccc(N)cc2c(O)c1C(=O)OCC | null | [Fe] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ncccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 75.3 | [{"value": 75.3, "product": "NC=1C=C2C(=C(C(=NC2=CC1)C(=O)OCC)C(=O)OCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.1, "product": "NC=1C=C2C(=C(C(=NC2=CC1)C(=O)OCC)C(=O)OCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of diethyl 4-hydroxy-6-nitroquinoline-2,3-dicarboxylate (4.4 g, 13 mM), powdered iron (6.6 g, 118 mM) and glacial acetic acid (18.5 g, 307 mM) in ethanol (80 mL) was refluxed for 20 hr under a nitrogen atmosphere. The reaction mixture was cooled and filtered and the filtrate was concentrated. The dark... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1 | Other | [Fe].C(C)O | null | null | CCOC(=O)c1nc2ccc([N+](=O)[O-])cc2c(O)c1C(=O)OCC>[Fe].C(C)O>CCOC(=O)c1nc2ccc(N)cc2c(O)c1C(=O)OCC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9d0a22ff2cb4115aad368a06d554f16 | CCc1cc(Br)c2c(O)c(C(=O)NN)c(C(=O)NN)nc2c1>>CCc1cc(Br)c2c(O)c3c(=O)[nH][nH]c(=O)c3nc2c1 | N(N)C(=O)C1=NC2=CC(=CC(=C2C(=C1C(=O)NN)O)Br)CC>>BrC=1C=2C(=C3C(=NC2C=C(C1)CC)C(NNC3=O)=O)O | NN[C:15](=[O:16])[c:17]1[c:10]([C:11](=[O:12])[NH:13][NH2:14])[c:8]([OH:9])[c:7]2[c:5]([Br:6])[cH:4][c:3]([CH2:2][CH3:1])[cH:20][c:19]2[n:18]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([Br:6])[c:7]2[c:8]([OH:9])[c:10]3[c:11](=[O:12])[nH:13][nH:14][c:15](=[O:16])[c:17]3[n:18][c:19]2[cH:20]1 | CCc1cc(Br)c2c(O)c(C(=O)NN)c(C(=O)NN)nc2c1 | CCc1cc(Br)c2c(O)c3c(=O)[nH][nH]c(=O)c3nc2c1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | f3dbb0a7ecffef3e204ef147736503e670fedb65b98cbf3d826138146a8353d2 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | O=c1[nH][nH]c(=O)c2nc3ccccc3cc12 | N-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[#7;a:4]:[c:5]):[c:6](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[NH;D2;+0:9]-[NH2;D1;+0:10]):[c:11]>>[O;D1;H0:8]=[c;H0;D3;+0:7]1:[nH;D2;+0:9]:[nH;D2;+0:10]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[c:3](:[#7;a:4]:[c:5]):[c:6]:1:[c:11] | 70 | [{"value": 70.0, "product": "BrC=1C=2C(=C3C(=NC2C=C(C1)CC)C(NNC3=O)=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.5, "product": "BrC=1C=2C(=C3C(=NC2C=C(C1)CC)C(NNC3=O)=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 81 | CELSIUS | null | null | A stirred mixture of 2,3-bishydrazinocarbonyl-5-bromo-7-ethyl-4-hydroxyquinoline (0.40 g, 1.1 mM) in glacial acetic acid (12 mL) was heated at 81° C. for 1.5 hr. After cooling to room temperature, the reaction mixture was filtered and the collected solids washed with acetic acid and air dried to provide the title compo... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | c1ccc2ncccc2c1 | C1=c2cc3ccccc3nc2=CNN1 | C1=c2cc3ccccc3nc2=CNN1 | Other | C(C)(=O)O | 81 | null | CCc1cc(Br)c2c(O)c(C(=O)NN)c(C(=O)NN)nc2c1>C(C)(=O)O>CCc1cc(Br)c2c(O)c3c(=O)[nH][nH]c(=O)c3nc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-29cf4cf9cdd54ff580a9152a0791fb0b | Cc1ccc(N)c([N+](=O)[O-])c1.ClCl>>Cc1cc(Cl)c(N)c([N+](=O)[O-])c1 | CC1=CC(=C(N)C=C1)[N+](=O)[O-].ClCl>>ClC1=C(N)C(=CC(=C1)C)[N+](=O)[O-] | [CH3:1][c:2]1[cH:3][cH:4][c:6]([NH2:7])[c:8]([N+:9](=[O:10])[O-:11])[cH:12]1.Cl[Cl:5]>>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[c:6]([NH2:7])[c:8]([N+:9](=[O:10])[O-:11])[cH:12]1 | Cc1ccc(N)c([N+](=O)[O-])c1.ClCl | Cc1cc(Cl)c(N)c([N+](=O)[O-])c1 | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Chlorination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Cl-[Cl;H0;D1;+0:1].[N;D1;H2:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3](-[N;D1;H2:2]):[c:4] | 25 | [{"value": 25.0, "product": "ClC1=C(N)C(=CC(=C1)C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.0, "product": "ClC1=C(N)C(=CC(=C1)C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a stirred solution of 4-methyl-2-nitroaniline (19.69 g, 129.4 mM) in chloroform (200 mL) under a nitrogen atmosphere was added dropwise a solution of chlorine (10.15 g, 285.9 mM) in chloroform (100 mL) while maintaining the reaction mixture temperature below 30° C. The reaction mixture was stirred for 3 days and the... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | C(Cl)(Cl)Cl | null | 72 | Cc1ccc(N)c([N+](=O)[O-])c1.ClCl>C(Cl)(Cl)Cl>Cc1cc(Cl)c(N)c([N+](=O)[O-])c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b5beb2924d104c099a4a39902f3b9c14 | Cc1cc(Cl)c(N)c([N+](=O)[O-])c1>>Cc1cc(Cl)cc([N+](=O)[O-])c1 | N(=O)[O-].[Na+].ClC1=C(N)C(=CC(=C1)C)[N+](=O)[O-].S(O)(O)(=O)=O>>ClC=1C=C(C=C(C1)[N+](=O)[O-])C | N[c:6]1[c:4]([Cl:5])[cH:3][c:2]([CH3:1])[cH:11][c:7]1[N+:8](=[O:9])[O-:10]>>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11]1 | Cc1cc(Cl)c(N)c([N+](=O)[O-])c1 | Cc1cc(Cl)cc([N+](=O)[O-])c1 | null | null | C(C)O.O | Reduction | OtherReaction | a069304de6b46c6d557b2e80c544464adc3bb98001f26c098e87c25f29d552f9 | a4f16f822d2806606c05d0c4baa1761ad37a11006840dde863a01a253bdff5dd | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2](-[Cl;D1;H0:3]):[c:4]):[c:5](-[#7;+:6]):[c:7]>>[#7;+:6]-[c:5](:[c:7]):[cH;D2;+0:1]:[c:2](-[Cl;D1;H0:3]):[c:4] | 92 | [{"value": 92.0, "product": "ClC=1C=C(C=C(C1)[N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.0, "product": "ClC=1C=C(C=C(C1)[N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | To a stirred mixture of 2-chloro-4-methyl-6-nitroaniline (7.39 g, 39.7 mM) and concentrated sulfuric acid (6.2 mL) in absolute ethanol (50 mL) at 0°-5° C. was slowly added a solution of sodium nitrite (6.85 g, 99.3 mM) in water (6 mL). The temperature of the reaction mixture was not allowed to exceed 5° C. during the a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C(C)O.O | null | 0.5 | Cc1cc(Cl)c(N)c([N+](=O)[O-])c1>C(C)O.O>Cc1cc(Cl)cc([N+](=O)[O-])c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4061f90aaff7419f9113b9addf8ac370 | O=c1[nH][nH]c(=O)c2c(O)c3ccc(Cl)cc3nc12>>O=c1[nH][nH]c(=O)c2c(O)c3ccc(Cl)cc3nc12 | CO.[OH-].OCC[N+](C)(C)C.ClC=1C=CC=2C(=C3C(=NC2C1)C(NNC3=O)=O)O.C1(=CC=CC=C1)C>>OCC[N+](C)(C)C.ClC=1C=CC=2C(=C3C(=NC2C1)C(NNC3=O)=O)O | [O:8]=[c:9]1[nH:10][nH:11][c:12](=[O:13])[c:14]2[c:15]([OH:16])[c:17]3[cH:18][cH:19][c:20]([Cl:21])[cH:22][c:23]3[n:24][c:25]12>>[O:8]=[c:9]1[nH:10][nH:11][c:12](=[O:13])[c:14]2[c:15]([OH:16])[c:17]3[cH:18][cH:19][c:20]([Cl:21])[cH:22][c:23]3[n:24][c:25]12 | O=c1[nH][nH]c(=O)c2c(O)c3ccc(Cl)cc3nc12 | O=c1[nH][nH]c(=O)c2c(O)c3ccc(Cl)cc3nc12 | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=c1[nH][nH]c(=O)c2nc3ccccc3cc12 | null | 55 | [{"value": 55.0, "product": "OCC[N+](C)(C)C.ClC=1C=CC=2C(=C3C(=NC2C1)C(NNC3=O)=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred suspension of 7-chloro-2,3-dihydro-10-hydroxypyridazino[4,5-b]quinoline-1,4-dione (1.00 g, 3.8 mM) in water (40 mL) was added choline hydroxide (0.86 mL, 3.8 mM, 50 weight per cent, aqueous solution). Toluene (250 mL) was added to the resulting solution and the mixture was concentrated using a rotary evapo... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1=c2cc3ccccc3nc2=CNN1 | null | O | null | null | O=c1[nH][nH]c(=O)c2c(O)c3ccc(Cl)cc3nc12>O>O=c1[nH][nH]c(=O)c2c(O)c3ccc(Cl)cc3nc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0d0496f4365345e6a41504bd3b92e14d | CCOC(=O)CCNc1c2ccc(Cl)cc2nc2c(=O)[nH][nH]c(=O)c12>>O=C(O)CCNc1c2ccc(Cl)cc2nc2c(=O)[nH][nH]c(=O)c12 | C(C)OC(=O)CCNC1=C2C(=NC=3C=C(C=CC13)Cl)C(NNC2=O)=O.Cl>>C(=O)(O)CCNC1=C2C(=NC=3C=C(C=CC13)Cl)C(NNC2=O)=O | CC[O:3][C:2](=[O:1])[CH2:4][CH2:5][NH:6][c:7]1[c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]2[n:15][c:16]2[c:17](=[O:18])[nH:19][nH:20][c:21](=[O:22])[c:23]12>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][NH:6][c:7]1[c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]2[n:15][c:16]2[c:17](=[O:18])[nH:19][nH:20][c:21](=[O:22])[c:23]12 | CCOC(=O)CCNc1c2ccc(Cl)cc2nc2c(=O)[nH][nH]c(=O)c12 | O=C(O)CCNc1c2ccc(Cl)cc2nc2c(=O)[nH][nH]c(=O)c12 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1[nH][nH]c(=O)c2nc3ccccc3cc12 | C-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] | 97 | [{"value": 97.0, "product": "C(=O)(O)CCNC1=C2C(=NC=3C=C(C=CC13)Cl)C(NNC2=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.8, "product": "C(=O)(O)CCNC1=C2C(=NC=3C=C(C=CC13)Cl)C(NNC2=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 10-(2-ethoxycarbonylethylamino)-7-chloro-2,3-dihydropyridazino[4,5-b]quinoline-1,4-dione (0.08 g, 0.22 mM) and 1N hydrochloric acid was refluxed for 1 hr and then cooled to room temperature and filtered. The collected orange solid was washed with water and air dried to provide (0.07 g, 97%) the title compo... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1=c2cc3ccccc3nc2=CNN1 | Other | null | null | null | CCOC(=O)CCNc1c2ccc(Cl)cc2nc2c(=O)[nH][nH]c(=O)c12>>O=C(O)CCNc1c2ccc(Cl)cc2nc2c(=O)[nH][nH]c(=O)c12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3dd4f599f9304ea3aa6b0fcf1031451d | CCOC(=O)CCN.NNc1c2ccc(Cl)cc2nc2c(=O)[nH][nH]c(=O)c12>>CCOC(=O)CCNc1c2ccc(Cl)cc2nc2c(=O)[nH][nH]c(=O)c12 | Cl.ClC=1C=CC=2C(=C3C(=NC2C1)C(NNC3=O)=O)NN.Cl.C(C)OC(CCN)=O>>C(C)OC(=O)CCNC1=C2C(=NC=3C=C(C=CC13)Cl)C(NNC2=O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][NH2:8].NN[c:9]1[c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]2[n:17][c:18]2[c:19](=[O:20])[nH:21][nH:22][c:23](=[O:24])[c:25]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][NH:8][c:9]1[c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]2[n:17][c:18]2[c:19](=[O:20])[nH:2... | CCOC(=O)CCN.NNc1c2ccc(Cl)cc2nc2c(=O)[nH][nH]c(=O)c12 | CCOC(=O)CCNc1c2ccc(Cl)cc2nc2c(=O)[nH][nH]c(=O)c12 | null | null | N1=CC=CC=C1.O | Heteroatom Alkylation and Arylation | OtherReaction | f98d784ec192c3194744583e79effe31cacfed7ba6bd47589340e7ccc1df453b | 5f0b2233a04d0388eef58efc20aa7249a5468ae58d751d6d6865b0a04a6912a5 | O=c1[nH][nH]c(=O)c2nc3ccccc3cc12 | N-N-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]2:[c:8]:[#7;a:9]:[#7;a:10]:[c:11](=[O;D1;H0:12]):[c:13]:2:1.[#8:14]-[C:15](=[O;D1;H0:16])-[C:17]-[C:18]-[NH2;D1;+0:19]>>[#8:14]-[C:15](=[O;D1;H0:16])-[C:17]-[C:18]-[NH;D2;+0:19]-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]2:[c:8]:[#7;a:9]:[#7;a... | 13 | [{"value": 13.0, "product": "C(C)OC(=O)CCNC1=C2C(=NC=3C=C(C=CC13)Cl)C(NNC2=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.3, "product": "C(C)OC(=O)CCNC1=C2C(=NC=3C=C(C=CC13)Cl)C(NNC2=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 7-chloro-2,3-dihydro-10-hydrazinopyridazino[4,5-b]quinoline-1,4-dione hydrochloride (1.0 g, 2.9 mM, as prepared in Example 44) and beta alanine ethyl ester hydrochloride (49.0 g, 320 mM) in pyridine (52 mL) was refluxed for 23 hr. After cooling, the vigorously stirred reaction mixture was diluted slowly wi... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary amine | Secondary amine | C1=c2cc3ccccc3nc2=CNN1 | C1=c2cc3ccccc3nc2=CNN1 | C1=c2cc3ccccc3nc2=CNN1 | Other | N1=CC=CC=C1.O | null | null | CCOC(=O)CCN.NNc1c2ccc(Cl)cc2nc2c(=O)[nH][nH]c(=O)c12>N1=CC=CC=C1.O>CCOC(=O)CCNc1c2ccc(Cl)cc2nc2c(=O)[nH][nH]c(=O)c12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-94d9309832e348ba9c46db768414dfd5 | O=c1[nH][nH]c(=O)c2c(O)c3ccc(Br)cc3nc12>>O=c1[nH][nH]c(=O)c2c(O)c3ccc(Br)cc3nc12 | BrC=1C=CC=2C(=C3C(=NC2C1)C(NNC3=O)=O)O.[OH-].OCC[N+](C)(C)C>>OCC[N+](C)(C)C.BrC=1C=CC=2C(=C3C(=NC2C1)C(NNC3=O)=O)O | [O:8]=[c:9]1[nH:10][nH:11][c:12](=[O:13])[c:14]2[c:15]([OH:16])[c:17]3[cH:18][cH:19][c:20]([Br:21])[cH:22][c:23]3[n:24][c:25]12>>[O:8]=[c:9]1[nH:10][nH:11][c:12](=[O:13])[c:14]2[c:15]([OH:16])[c:17]3[cH:18][cH:19][c:20]([Br:21])[cH:22][c:23]3[n:24][c:25]12 | O=c1[nH][nH]c(=O)c2c(O)c3ccc(Br)cc3nc12 | O=c1[nH][nH]c(=O)c2c(O)c3ccc(Br)cc3nc12 | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=c1[nH][nH]c(=O)c2nc3ccccc3cc12 | null | 78 | [{"value": 78.0, "product": "OCC[N+](C)(C)C.BrC=1C=CC=2C(=C3C(=NC2C1)C(NNC3=O)=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.2, "product": "OCC[N+](C)(C)C.BrC=1C=CC=2C(=C3C(=NC2C1)C(NNC3=O)=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 7-bromo-2,3-dihydro-10-hydroxypyridazino[4,5-b]quinoline-1,4-dione (0.600g, 1.95 mM) in methanol (20 mL) was added choline hydroxide (0.24 g, 1.98 mM, 45% solution in methanol). The resulting solution was concentrated and the solid yellow residue was recrystallized from ethanol to provide (0.62 g, 78... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1=c2cc3ccccc3nc2=CNN1 | null | CO | null | null | O=c1[nH][nH]c(=O)c2c(O)c3ccc(Br)cc3nc12>CO>O=c1[nH][nH]c(=O)c2c(O)c3ccc(Br)cc3nc12 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0a45a609ac2e45e08721ea94db9274b3 | CC(C)[C@H](NC(=O)OC(C)(C)C)C(N)=O.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>>CC(C)[C@H](NC(=O)OC(C)(C)C)C(N)=S | C(=O)(OC(C)(C)C)N[C@@H](C(C)C)C(=O)N.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>C(=O)(OC(C)(C)C)N[C@@H](C(C)C)C(N)=S | O=[C:13]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[NH2:14].COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:15])S2)cc1>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13]([NH2:14])=[S:15] | CC(C)[C@H](NC(=O)OC(C)(C)C)C(N)=O.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1 | CC(C)[C@H](NC(=O)OC(C)(C)C)C(N)=S | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 613c2435b38505a097e2fde19577156c7ebdf46c5ee2d9d02c5db3750225691b | bad40f822f57ef1603ddc3833f08662df4bfc24add9b681d08e1ec3f67723ed7 | null | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[C;H0;D3;+0:2](-[N;D1;H2:3])-[C:4](-[C:5])-[#7:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13]>>[C:5]-[C:4](-[#7:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13])-[C;H0;D3;+0:2](-... | 70 | [{"value": 70.0, "product": "C(=O)(OC(C)(C)C)N[C@@H](C(C)C)C(N)=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.4, "product": "C(=O)(OC(C)(C)C)N[C@@H](C(C)C)C(N)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Boc-valineamide (0.5 g) was stirred in dry THF at room temperature under argon. Lawesson's reagent (1.56 g, 0.6 eq) was added and the mixture was stirred overnight. The solvent was evaporated and the residue chromatographed (silica, 2.5% methanol/dichloromethane) to give the title compound as a white solid (0.373 g, 70... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amide.Monosulfide.Monosulfide | Thioamide | c1ccccc1.P1SPS1.c1ccccc1 | null | null | Other | C1CCOC1 | null | 8 | CC(C)[C@H](NC(=O)OC(C)(C)C)C(N)=O.COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1>C1CCOC1>CC(C)[C@H](NC(=O)OC(C)(C)C)C(N)=S |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b0f251ba8a8b43138ec22405d9b99942 | CC(C)(C)[Si](C)(C)Cl.O[C@@H]1CCC[C@H]1O>>CC(C)(C)[Si](C)(C)O[C@@H]1CCC[C@H]1O | [C@@H]1([C@@H](CCC1)O)O.[Si](C)(C)(C(C)(C)C)Cl.N1C=NC=C1>>O([Si](C)(C)C(C)(C)C)[C@H]1[C@@H](CCC1)O | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][C@@H:9]1[CH2:10][CH2:11][CH2:12][C@H:13]1[OH:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C@@H:9]1[CH2:10][CH2:11][CH2:12][C@H:13]1[OH:14] | CC(C)(C)[Si](C)(C)Cl.O[C@@H]1CCC[C@H]1O | CC(C)(C)[Si](C)(C)O[C@@H]1CCC[C@H]1O | null | null | CN(C)C=O | Protection | Alcohol protection with silyl ethers | e19079a85b3e2f818dbb25a774b915f0e7349126f5b76d72c22f1c90edfa8480 | 16de9d9d08d1cc67ec96e76fc213a6b49c0af7979ac901a377ee705ba5071899 | C1CCCC1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9](-[OH;D1;+0:10])-[C:11]>>[C:8]-[C:9](-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7])-[C:11] | null | [] | 25 | CELSIUS | 8 | HOUR | To a mixture of t-butyldimethylsilyl chloride (5.08 g, 33.7 mmol) and imidazole (2.30 g, 33.7 mmol) in DMF (10 mL), a solution of trans-1,2-cyclopentanediol in DMF (4 mL) was added. The reaction mixture was stirred overnight at 25° C. The reaction mixture was diluted with ice water and extracted with ether. The ether e... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | TMS ether protective group | null | null | C1CCCC1 | HCl | CN(C)C=O | 25 | 8 | CC(C)(C)[Si](C)(C)Cl.O[C@@H]1CCC[C@H]1O>CN(C)C=O>CC(C)(C)[Si](C)(C)O[C@@H]1CCC[C@H]1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9364a4a06ced401991545a8820488b8f | [Li][CH2]CCC.c1ccc(COCn2ccnc2)cc1>>CC(C)C(O)c1nccn1COCc1ccccc1 | C(C1=CC=CC=C1)OCN1C=NC=C1.C1CCOC1.[Li]CCCC>>C(C1=CC=CC=C1)OCN1C(=NC=C1)C(C(C)C)O | [Li][CH2][CH2:1][CH2:2][CH3:3].[cH:6]1[n:7][cH:8][cH:9][n:10]1[CH2:11][O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][CH:2]([CH3:3])[CH:4]([OH:5])[c:6]1[n:7][cH:8][cH:9][n:10]1[CH2:11][O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | [Li][CH2]CCC.c1ccc(COCn2ccnc2)cc1 | CC(C)C(O)c1nccn1COCc1ccccc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 831678e4cbc436395546aca685c7c5e29bb63644a93b6ae8aa2e54462c0cc0e9 | 4ccdf76089dbbce498de631b1bc2db02ddd1c7c47d40bd0396e240884451beff | c1ccc(COCn2ccnc2)cc1 | [C;D1;H3:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2]-[Li].[C:4]-[#7;a:5]1:[c:6]:[c:7]:[#7;a:8]:[cH;D2;+0:9]:1>>[C:4]-[#7;a:5]1:[c:6]:[c:7]:[#7;a:8]:[c;H0;D3;+0:9]:1-[C:10](-[O;D1;H1:11])-[CH;D3;+0:2](-[C;D1;H3:1])-[CH3;D1;+0:3] | 69 | [{"value": 69.0, "product": "C(C1=CC=CC=C1)OCN1C(=NC=C1)C(C(C)C)O", "details": "PERCENTYIELD", "is_desired": false}] | -40 | CELSIUS | 15 | MINUTE | 1-benzyloxymethylimidazole prepared according to the procedure of Ngochindo, R., J. Chem. Res. (S), 58 (1990)) (3.76 g, 20 mmol), and THF (40 mL) at -40° C., was treated dropwise with n-BuLi (8.4 mL, 21 mmol, 2.5M in hexane). The resulting solution was stirred at -40° C. for 15 min, and i-butyraldehyde (2.0 mL, 22 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Alkyl lithium | Secondary alcohol | c1c[nH]cn1 | c1ncc[nH]1 | c1ncc[nH]1.c1ccccc1 | null | O | -40 | 0.25 | [Li][CH2]CCC.c1ccc(COCn2ccnc2)cc1>O>CC(C)C(O)c1nccn1COCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-af96ced584d54df9885b41c24ce0e973 | CC(=O)OC(C)(C)C.CC(C)C(=O)c1nc(COCc2ccccc2)c[nH]1>>CC(C)C(O)(CC(=O)OC(C)(C)C)c1nccn1COCc1ccccc1 | CN(C)P(=O)(N(C)C)N(C)C.C(=O)([O-])[O-].[K+].[K+].C(C)(=O)OC(C)(C)C.[Li]CCCC.C(C1=CC=CC=C1)OCC=1N=C(NC1)C(C(C)C)=O.C(C)(C)NC(C)C>>C(C1=CC=CC=C1)OCN1C(=NC=C1)C(CC(=O)OC(C)(C)C)(C(C)C)O | [CH3:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13].[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[c:14]1[n:15][c:16]([CH2:19][O:20][CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:17][nH:18]1>>[CH3:1][CH:2]([CH3:3])[C:4]([OH:5])([CH2:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[c:14]1[n:15][cH:16][cH:17... | CC(=O)OC(C)(C)C.CC(C)C(=O)c1nc(COCc2ccccc2)c[nH]1 | CC(C)C(O)(CC(=O)OC(C)(C)C)c1nccn1COCc1ccccc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | d9dc4e073f3bc32a587d45cd9254c140ef04fd88ac7b2286fe9f047820f70927 | 74b8d38f3ae0a76226c0d6ae6220b5ec0c4d96c96094da6befdb2ae8e1120e84 | c1ccc(COCn2ccnc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](-[CH3;D1;+0:7])=[O;D1;H0:8].[C:9]-[#8:10]-[CH2;D2;+0:11]-[c;H0;D3;+0:12]1:[#7;a:13]:[c:14](-[C;H0;D3;+0:15](=[O;H0;D1;+0:16])-[C:17](-[C;D1;H3:18])-[C;D1;H3:19]):[nH;D2;+0:20]:[c:21]:1>>[C:9]-[#8:10]-[CH2;D2;+0:11]-[n;H0;D3;+0:20]1:[c:21]:[cH;D2;+0:12]:[#7;a:13... | 90 | [{"value": 90.0, "product": "C(C1=CC=CC=C1)OCN1C(=NC=C1)C(CC(=O)OC(C)(C)C)(C(C)C)O", "details": "PERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | null | null | Diisopropylamine (83 μL, 0.59 mmol) and THF (1.5 mL) were cooled to -40° C. and n-BuLi (188 μL, 0.47 mmol, 2.5M in hexane) was added. The reaction mixture was warmed to -10° C. and stirred for 15 m, recooled to -70° C. and t-butyl acetate (63 μL, 0.47 mmol) was added. The reaction was stirred for 5 m, and HMPA (254 μL,... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ether | Ester.Ether.Tertiary alcohol | c1c[nH]cn1 | c1ncc[nH]1 | c1ncc[nH]1.c1ccccc1 | null | C1CCOC1 | -10 | null | CC(=O)OC(C)(C)C.CC(C)C(=O)c1nc(COCc2ccccc2)c[nH]1>C1CCOC1>CC(C)C(O)(CC(=O)OC(C)(C)C)c1nccn1COCc1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0fb4566f15574ed1bc3456297724c43f | CCOC(=O)c1cc2ccccc2n(C(C)C)c1=O>>CC(C)n1c(=O)c(C(=O)O)cc2ccccc21 | C(C)(C)N1C(C(=CC2=CC=CC=C12)C(=O)OCC)=O.[OH-].[Na+].C(C)O>>C(C)(C)N1C(C(=CC2=CC=CC=C12)C(=O)O)=O | CC[O:10][C:8]([c:7]1[c:5](=[O:6])[n:4]([CH:2]([CH3:1])[CH3:3])[c:17]2[c:12]([cH:11]1)[cH:13][cH:14][cH:15][cH:16]2)=[O:9]>>[CH3:1][CH:2]([CH3:3])[n:4]1[c:5](=[O:6])[c:7]([C:8](=[O:9])[OH:10])[cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12 | CCOC(=O)c1cc2ccccc2n(C(C)C)c1=O | CC(C)n1c(=O)c(C(=O)O)cc2ccccc21 | null | null | O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc2ccccc2[nH]1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 88.3 | [{"value": 88.3, "product": "C(C)(C)N1C(C(=CC2=CC=CC=C12)C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 1.55 g of ethyl 1-isopropyl-2(1H)-quinolone-3-carboxylate and 0.28 g of sodium hydroxide in a solvent mixture of 10 ml of ethanol and 2 ml of water was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and after addition of dil. hydrochloric acid, the precipitated s... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2ncccc2c1 | Other | O | null | 8 | CCOC(=O)c1cc2ccccc2n(C(C)C)c1=O>O>CC(C)n1c(=O)c(C(=O)O)cc2ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8547a040ad9a425c98f22d4b4c6c403c | CC(C)Nc1ccccc1CO>>CC(C)Nc1ccccc1C=O | C(C)(C)NC1=C(CO)C=CC=C1.ClC=1C(C(=C(C(C1Cl)=O)C#N)C#N)=O>>C(C)(C)NC1=C(C=O)C=CC=C1 | [CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][OH:12]>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH:11]=[O:12] | CC(C)Nc1ccccc1CO | CC(C)Nc1ccccc1C=O | null | null | O1CCOCC1 | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 80.1 | [{"value": 80.1, "product": "C(C)(C)NC1=C(C=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 9.6 g of 2-isopropylaminobenzyl alcohol in 200 ml of dioxane was added 13.2 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in several portions, followed by stirring for an hour. The solvent was evaporated, the reaction solution was concentrated, and methylene chloride was added thereto, followed ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | O1CCOCC1 | null | null | CC(C)Nc1ccccc1CO>O1CCOCC1>CC(C)Nc1ccccc1C=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6ea71cac5fe24314936a22d13c05f389 | CC(C)Nc1ccccc1C=O.CCOC(=O)CC(=O)OCC>>CCOC(=O)c1cc2ccccc2n(C(C)C)c1=O | C(C)(C)NC1=C(C=O)C=CC=C1.C(CC(=O)OCC)(=O)OCC.C([O-])(O)=O.[Na+]>>C(C)(C)N1C(C(=CC2=CC=CC=C12)C(=O)OCC)=O | O=[CH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[NH:14][CH:15]([CH3:16])[CH3:17].CCO[C:18]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[n:14]([CH:15]([CH3:16])[CH3:17])[c:18]1=[O:19] | CC(C)Nc1ccccc1C=O.CCOC(=O)CC(=O)OCC | CCOC(=O)c1cc2ccccc2n(C(C)C)c1=O | null | null | C(C)(=O)OC(C)=O | Aromatic Heterocycle Formation | OtherReaction | 729ffe8850d05b6f2f8f8601c180def2bd405d714b65f772032554626ca5b59d | e01ead31c330dcfd1f5449feed0e578553ffcacb3b875032b5383c9a1ab25b8b | O=c1ccc2ccccc2[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].O=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11](-[NH;D2;+0:12]-[C:13](-[C;D1;H3:14])-[C;D1;H3:15]):[c:16]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:3]1:[cH;D2;+0:8]:[c:9](:[c:10]):[c:11](:[c:16]):[n;H0;D3;+0:12](-[C:13](-[C;D1;H3:14])-[C;D1;H3:1... | 61.3 | [{"value": 61.3, "product": "C(C)(C)N1C(C(=CC2=CC=CC=C12)C(=O)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A solution of 7.5 g of 2-isopropylaminobenzaldehyde, 11.0 g of diethyl malonate and 11.6 g of sodium bicarbonate in 800 ml of acetic anhydride was stirred under heating at 100° C. for 15 hours. After evaporation of the solvent under reduced pressure, water was added, followed by extraction with ethyl acetate. The organ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Ester.Secondary amine | Ester | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | C(C)(=O)OC(C)=O | 100 | null | CC(C)Nc1ccccc1C=O.CCOC(=O)CC(=O)OCC>C(C)(=O)OC(C)=O>CCOC(=O)c1cc2ccccc2n(C(C)C)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-18f7f5d0bdf24923973a1222b73ecdad | CCOC(=O)c1c(-c2ccc3c(c2)OCO3)c2ccccc2[nH]c1=O>>O=C(O)c1c(-c2ccc3c(c2)OCO3)c2ccccc2[nH]c1=O | Cl.C(C)OC(=O)C=1C(NC2=CC=CC=C2C1C1=CC2=C(C=C1)OCO2)=O.CO.[OH-].[K+]>>C1OC=2C=C(C=CC2O1)C1=C(C(NC2=CC=CC=C12)=O)C(=O)O | CC[O:3][C:2](=[O:1])[c:4]1[c:5](-[c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11]2)[O:12][CH2:13][O:14]3)[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[nH:21][c:22]1=[O:23]>>[O:1]=[C:2]([OH:3])[c:4]1[c:5](-[c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11]2)[O:12][CH2:13][O:14]3)[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[nH:21][c:22]1=[O:23] | CCOC(=O)c1c(-c2ccc3c(c2)OCO3)c2ccccc2[nH]c1=O | O=C(O)c1c(-c2ccc3c(c2)OCO3)c2ccccc2[nH]c1=O | null | null | O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1cc(-c2ccc3c(c2)OCO3)c2ccccc2[nH]1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 95.4 | [{"value": 95.4, "product": "C1OC=2C=C(C=CC2O1)C1=C(C(NC2=CC=CC=C12)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.4, "product": "C1OC=2C=C(C=CC2O1)C1=C(C(NC2=CC=CC=C12)=O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1,2-dihydro-4-(3,4-methylenedioxyphenyl)-2-oxo-3-quinoline carboxylic acid ethyl ester (40 g, 118.6 mmol), methanol (200 ml), water (300 ml) and potassium hydroxide (33.3 g, 593.5 mmol) was refluxed with heat for 40 hours. To the reaction mixture was added 110 ml of 6N-HCl to acidify the mixture to obtain ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)OCO2.c1cnc2ccccc2c1 | Other | O | null | null | CCOC(=O)c1c(-c2ccc3c(c2)OCO3)c2ccccc2[nH]c1=O>O>O=C(O)c1c(-c2ccc3c(c2)OCO3)c2ccccc2[nH]c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-08a65d3d86274d87908614df5eeda1f8 | O=C(O)c1c(-c2ccc3c(c2)OCO3)c2ccccc2[nH]c1=O.O=P(Cl)(Cl)Cl>>O=C1c2cc3c(cc2-c2c1c(Cl)nc1ccccc21)OCO3 | C1OC=2C=C(C=CC2O1)C1=C(C(NC2=CC=CC=C12)=O)C(=O)O.P(=O)(Cl)(Cl)Cl>>ClC1=NC2=CC=CC=C2C2=C1C(C1=CC3=C(C=C12)OCO3)=O | O=[c:11]1[c:10]([C:2](O)=[O:1])[c:9](-[c:8]2[cH:3][cH:4][c:5]3[c:6]([cH:7]2)[O:20][CH2:21][O:22]3)[c:19]2[c:14]([nH:13]1)[cH:15][cH:16][cH:17][cH:18]2.O=P(Cl)(Cl)[Cl:12]>>[O:1]=[C:2]1[c:3]2[cH:4][c:5]3[c:6]([cH:7][c:8]2-[c:9]2[c:10]1[c:11]([Cl:12])[n:13][c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]21)[O:20][CH2:21][O:22]3 | O=C(O)c1c(-c2ccc3c(c2)OCO3)c2ccccc2[nH]c1=O.O=P(Cl)(Cl)Cl | O=C1c2cc3c(cc2-c2c1c(Cl)nc1ccccc21)OCO3 | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 543e37a7a1f36d75ee988a367790d70acab5cef0bd77b8e407415edb03f42eb1 | 3222cccc60f66cbdb8ac8bb7a1f67e9f671c77d8cc441c4fc8b05ddd04bfbcfc | O=C1c2cc3c(cc2-c2c1cnc1ccccc21)OCO3 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c:5](-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]-[#8:11]):[c:12]:[c:13](:[c:14]):[nH;D2;+0:15]:[c;H0;D3;+0:16]:1=O>>[#8:11]-[c:10]:[c:9]:[c;H0;D3;+0:8]1:[c:6](:[c:7])-[c:5]2:[c:12]:[c:13](:[c:14]):[n;H0;D2;+0:15]:[c;H0;D3;+0:16](-[Cl;H0;D1;+0:1]):[c:4]:2... | 59.9 | [{"value": 59.9, "product": "ClC1=NC2=CC=CC=C2C2=C1C(C1=CC3=C(C=C12)OCO3)=O", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A mixture of 1,2-dihydro-4-(3,4-methylenedioxyphenyl)-2-oxo-3-quinoline carboxylic acid obtained in reference example 1 (10 g, 32.3 mmol) and phosphorous oxychloride (100 ml, 1.07 mol) was refluxed with heat for 4 hours. The reaction mixture was distilled to dryness and washed with n-hexane several times. To the residu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Aromatic halide.Ketone | c1ccc2c(c1)OCO2.c1cnc2ccccc2c1 | c1ccc2c(c1)ncc1c2c2cc3c(cc2C1)OCO3 | c1ccc2c(c1)ncc1c2c2cc3c(cc2C1)OCO3 | HCl | O1CCCC1 | 90 | null | O=C(O)c1c(-c2ccc3c(c2)OCO3)c2ccccc2[nH]c1=O.O=P(Cl)(Cl)Cl>O1CCCC1>O=C1c2cc3c(cc2-c2c1c(Cl)nc1ccccc21)OCO3 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5080020aec3640ada6d73af7d0efbd44 | CCOC(=O)c1c(-c2ccccc2)c2ccccc2[nH]c1=O>>O=C(O)c1c(-c2ccccc2)c2ccccc2[nH]c1=O | Cl.C(C)OC(=O)C=1C(NC2=CC=CC=C2C1C1=CC=CC=C1)=O.C(C)O.[OH-].[K+]>>C1(=CC=CC=C1)C1=C(C(NC2=CC=CC=C12)=O)C(=O)O | CC[O:3][C:2](=[O:1])[c:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[nH:18][c:19]1=[O:20]>>[O:1]=[C:2]([OH:3])[c:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[nH:18][c:19]1=[O:20] | CCOC(=O)c1c(-c2ccccc2)c2ccccc2[nH]c1=O | O=C(O)c1c(-c2ccccc2)c2ccccc2[nH]c1=O | null | null | O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1cc(-c2ccccc2)c2ccccc2[nH]1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 93.1 | [{"value": 92.9, "product": "C1(=CC=CC=C1)C1=C(C(NC2=CC=CC=C12)=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.1, "product": "C1(=CC=CC=C1)C1=C(C(NC2=CC=CC=C12)=O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1,2-dihydro-4-phenyl-2-oxo-3-quinoline carboxylic acid ethyl ester (5 g, 17 mmol), ethanol (20 ml), water (40 ml) and potassium hydroxide (5 g, mmol) was refluxed with heat for 1.5 hours. To the reaction mixture was added 60 ml of 2N-HCl to acidify the mixture to obtain a precipitated crystal by filtration... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cnc2ccccc2c1 | Other | O | null | null | CCOC(=O)c1c(-c2ccccc2)c2ccccc2[nH]c1=O>O>O=C(O)c1c(-c2ccccc2)c2ccccc2[nH]c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-40686f94c8ff48678189869d94122470 | CCOC(=O)c1c(-c2ccccc2)c2ccc(C)cc2[nH]c1=O>>Cc1ccc2c3c(c(=O)[nH]c2c1)C(=O)c1ccccc1-3 | C(C)OC(=O)C=1C(NC2=CC(=CC=C2C1C1=CC=CC=C1)C)=O>>CC1=CC=C2C3=C(C(NC2=C1)=O)C(C1=CC=CC=C13)=O | CCO[C:13]([c:7]1[c:6](-[c:20]2[cH:15][cH:19][cH:18][cH:17][cH:16]2)[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:12][c:11]2[nH:10][c:8]1=[O:9])=[O:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]3[c:7]([c:8](=[O:9])[nH:10][c:11]2[cH:12]1)[C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1-3 | CCOC(=O)c1c(-c2ccccc2)c2ccc(C)cc2[nH]c1=O | Cc1ccc2c3c(c(=O)[nH]c2c1)C(=O)c1ccccc1-3 | null | null | S(O)(O)(=O)=O | C-C Coupling | OtherReaction | 74cf47bc32c60b614b02500a53806bb8f623818590d3a4063f8137ba05983240 | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | O=C1c2ccccc2-c2c1c(=O)[nH]c1ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4](-[c;H0;D3;+0:5]2:[cH;D2;+0:6]:[cH;D2;+0:7]:[c:8]:[c:9]:[cH;D2;+0:10]:2):[c:11]:[c:12]:[#7;a:13]:[c:14]:1=[O;D1;H0:15]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[c:3]2:[c:4](:[c:11]:[c:12]:[#7;a:13]:[c:14]:2=[O;D1;H0:15])-[c;H0;D3;+0:5]2:[cH;D2;+0:7]:[c:8]:[c:9]:[cH;D2;+0:10]:[c;H0;D3;... | null | [] | 95 | CELSIUS | null | null | A mixture of 1,2-dihydro-4-phenyl-7-methyl-2-oxo-3-quinoline carboxylic acid ethyl ester (2.5 g, 8.1 mmol) and conc. sulfuric acid (20 ml) was stirred with heat at 95° C. for 10 hours. The reaction mixture was poured into ice water to obtain a crystal precipitated by filtration. The crystal obtained was washed with wat... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | c1ccccc1 | C1c2ccccc2c2c1cnc1ccccc12 | C1c2ccccc2c2c1cnc1ccccc12 | HO- | S(O)(O)(=O)=O | 95 | null | CCOC(=O)c1c(-c2ccccc2)c2ccc(C)cc2[nH]c1=O>S(O)(O)(=O)=O>Cc1ccc2c3c(c(=O)[nH]c2c1)C(=O)c1ccccc1-3 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d9236b54d4954b7aa9b9f3b9d4ae71c7 | Cc1ccc2c3c(c(=O)[nH]c2c1)C(=O)c1ccccc1-3.O=P(Cl)(Cl)Cl>>Cc1ccc2c3c(c(Cl)nc2c1)C(=O)c1ccccc1-3 | CC1=CC=C2C3=C(C(NC2=C1)=O)C(C1=CC=CC=C13)=O.P(=O)(Cl)(Cl)Cl>>ClC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)C | O=[c:8]1[c:7]2[c:6]([c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:12][c:11]3[nH:10]1)-[c:20]1[c:15]([cH:16][cH:17][cH:18][cH:19]1)[C:13]2=[O:14].O=P(Cl)(Cl)[Cl:9]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]3[c:7]([c:8]([Cl:9])[n:10][c:11]2[cH:12]1)[C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1-3 | Cc1ccc2c3c(c(=O)[nH]c2c1)C(=O)c1ccccc1-3.O=P(Cl)(Cl)Cl | Cc1ccc2c3c(c(Cl)nc2c1)C(=O)c1ccccc1-3 | null | null | null | Functional Group Interconversion | OtherReaction | 5e9dd541e33e00251f4cb33b88e87b9d504018c590d84ac6a9372bbc42fd7bc5 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C1c2ccccc2-c2c1cnc1ccccc21 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4](:[c:5]):[c:6]:[c:7]:[c:8]:1-[C:9](=[O;D1;H0:10])-[c:11]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4](:[c:5]):[c:6]:[c:7]:[c:8]:1-[C:9](=[O;D1;H0:10])-[c:11] | 73.4 | [{"value": 73.4, "product": "ClC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-methyl-5H-indeno[2,1-c]quinoline-6,7-dion obtained in reference example 5 (700 mg, 2.7 mmol) and phosphorous oxychloride (10 ml, 107 mmol) was refluxed with heat for 1.5 hours. The reaction mixture was distilled to dryness. To the residue was added water to obtain a crystal precipitated by filtration. Th... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | C1c2ccccc2c2c1cnc1ccccc12 | c1ccc2c(c1)Cc1cnc3ccccc3c12 | c1ccc2c(c1)Cc1cnc3ccccc3c12 | HCl | null | null | null | Cc1ccc2c3c(c(=O)[nH]c2c1)C(=O)c1ccccc1-3.O=P(Cl)(Cl)Cl>>Cc1ccc2c3c(c(Cl)nc2c1)C(=O)c1ccccc1-3 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c39dc7ddfdaf41718ff28171b32b7253 | CCC(CC)(C(=O)[O-])C(=O)[O-].CCO.COc1ccc(C(=O)c2ccccc2)c(N)c1>>CCOC(=O)c1c(-c2ccccc2)c2ccc(OC)cc2[nH]c1=O | C(C)O.NC1=C(C(=O)C2=CC=CC=C2)C=CC(=C1)OC.C(C)C(C(=O)[O-])(C(=O)[O-])CC>>C(C)OC(=O)C=1C(NC2=CC(=CC=C2C1C1=CC=CC=C1)OC)=O | CC[C:6](CC)([C:4]([O-])=[O:5])[C:23]([O-])=[O:24].[CH3:1][CH2:2][OH:3].O=[C:7]([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][c:21]1[NH2:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[c:14]2[cH:15][cH:16][c:17]([O:18][CH3:19])[c... | CCC(CC)(C(=O)[O-])C(=O)[O-].CCO.COc1ccc(C(=O)c2ccccc2)c(N)c1 | CCOC(=O)c1c(-c2ccccc2)c2ccc(OC)cc2[nH]c1=O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | a22b280606df717de5da2cb298275accbc9bf15ee6ef21165528469877751748 | 459e7381b48255c35b0f54131b1cc18a13864ee1e81675dcd1a560b0b90e67dd | O=c1cc(-c2ccccc2)c2ccccc2[nH]1 | C-C-[C;H0;D4;+0:1](-C-C)(-[C;H0;D3;+0:2](-[O-])=[O;D1;H0:3])-[C;H0;D3;+0:4](-[O-])=[O;D1;H0:5].O=[C;H0;D3;+0:6](-[c:7](:[c:8]):[c:9](-[NH2;D1;+0:10]):[c:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16].[C;D1;H3:17]-[C:18]-[OH;D1;+0:19]>>[C;D1;H3:17]-[C:18]-[O;H0;D2;+0:19]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c;H0;D3;+0:1]1:... | 90.2 | [{"value": 90.2, "product": "C(C)OC(=O)C=1C(NC2=CC(=CC=C2C1C1=CC=CC=C1)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | null | null | A mixture of 2-amino-4-methoxybenzophenone (20 g, 88 mmol), diethylmalonate (26.7 ml, 176 mmol), 1,8-diazabicyclo[5,2,0]-undeca-7-en (DBU) (0.66 ml, 4.4 mmol) was stirred with heat at 160° C. for 2 hours. The reaction mixture was cooled by air. To the cooled mixture was added ethanol (30 ml) to obtain a precipitated cr... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Primary amine | Ester | c1ccccc1 | c1cnc2ccccc2c1 | c1ccccc1.c1cnc2ccccc2c1 | HO- | null | 160 | null | CCC(CC)(C(=O)[O-])C(=O)[O-].CCO.COc1ccc(C(=O)c2ccccc2)c(N)c1>>CCOC(=O)c1c(-c2ccccc2)c2ccc(OC)cc2[nH]c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bd6b84b0847d406aae39ab734c84c1c7 | O=C1c2ccccc2-c2c1[nH]c(=O)c1ccccc21.O=P(Cl)(Cl)Cl>>O=C1c2ccccc2-c2c1nc(Cl)c1ccccc21 | C1=C2C3=C(NC(C2=CC=C1)=O)C(C1=CC=CC=C13)=O.P(=O)(Cl)(Cl)Cl>>ClC1=NC2=C(C3=CC=CC=C13)C1=CC=CC=C1C2=O | O=[c:12]1[nH:11][c:10]2[c:9]([c:19]3[c:14]1[cH:15][cH:16][cH:17][cH:18]3)-[c:8]1[c:3]([cH:4][cH:5][cH:6][cH:7]1)[C:2]2=[O:1].O=P(Cl)(Cl)[Cl:13]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2-[c:9]2[c:10]1[n:11][c:12]([Cl:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]21 | O=C1c2ccccc2-c2c1[nH]c(=O)c1ccccc21.O=P(Cl)(Cl)Cl | O=C1c2ccccc2-c2c1nc(Cl)c1ccccc21 | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | 1c742d69c8b6c3cd5770be5e58f0553876f7d2550b6be59e9046e3287dd7aaba | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C1c2ccccc2-c2c1ncc1ccccc21 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4](:[c:5]:[c:6]:[c:7]:1:[c:8])-[C:9](=[O;D1;H0:10])-[c:11]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4](:[c:5]:[c:6]:[c:7]:1:[c:8])-[C:9](=[O;D1;H0:10])-[c:11] | 78.7 | [{"value": 78.7, "product": "ClC1=NC2=C(C3=CC=CC=C13)C1=CC=CC=C1C2=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6H-indeno[2,1-c]isoquinoline-5,7-dion obtained in reference example 16 (26.6 g, 108 mmol) and phosphorous oxychloride (300 ml) was refluxed with heat in the presence of 1 ml of N,N-dimethylformamide for 2 hours. The reaction mixture was distilled to dryness. To the residue was added ice water to obtain a c... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | C1c2ccccc2c2c1ncc1ccccc12 | c1ccc2c(c1)Cc1ncc3ccccc3c12 | c1ccc2c(c1)Cc1ncc3ccccc3c12 | HCl | CN(C=O)C | null | null | O=C1c2ccccc2-c2c1[nH]c(=O)c1ccccc21.O=P(Cl)(Cl)Cl>CN(C=O)C>O=C1c2ccccc2-c2c1nc(Cl)c1ccccc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-afb2bac37106446f80150be5390395af | CN(C)CCN.O=C1c2ccccc2-c2c1c(Cl)nc1cc(F)ccc21>>CN(C)CCNc1nc2cc(F)ccc2c2c1C(=O)c1ccccc1-2.Cl.Cl | ClC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)F.CN(CCN)C>>Cl.Cl.CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)F | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH2:6].[c:7]1([Cl:26])[n:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][c:15]2[c:16]2[c:17]1[C:18](=[O:19])[c:20]1[cH:21][cH:22][cH:23][cH:24][c:25]1-2>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][c:7]1[n:8][c:9]2[cH:10][c:11]([F:12])[cH:13][cH:14][c:15]2[c:16]2[c:17]1[C:18](=[O:19])[c:20... | CN(C)CCN.O=C1c2ccccc2-c2c1c(Cl)nc1cc(F)ccc21 | CN(C)CCNc1nc2cc(F)ccc2c2c1C(=O)c1ccccc1-2.Cl.Cl | null | null | null | Functional Group Addition | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 18f2f261f905c62bee5916bb9821e685b82d92037febfdc52d35c3760f226e9a | 6f78585f8136bfeb64030c4a3c4021c4cf8a554288637e24070b99b83b5f9b48 | O=C1c2ccccc2-c2c1cnc1ccccc21 | [C:1]-[C:2]-[NH2;D1;+0:3].[Cl;H0;D1;+0:4]-[c;H0;D3;+0:5](:[#7;a:6]:[c:7]):[c:8](:[c:9])-[C:10](=[O;D1;H0:11])-[c:12]>>[C:1]-[C:2]-[NH;D2;+0:3]-[c;H0;D3;+0:5](:[#7;a:6]:[c:7]):[c:8](:[c:9])-[C:10](=[O;D1;H0:11])-[c:12].[ClH;D0;+0:4] | 68.6 | [{"value": 34.3, "product": "Cl.Cl.CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.6, "product": "Cl.Cl.CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a suspension of 6-chloro-3-fluoro-7H-indeno[2,1-c]quinoline-7-on (860 mg, 3.0 mmol) in pyrydine (10 ml) was added N,N-dimethylethylenediamine (800 mg, 9.0 mmol), and the mixture was stirred with heat at 90° C. for 12 hours. The reaction mixture was distilled to dryness. To the residue was added water and chloroform ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)Cc1cnc3ccccc3c12 | c1ccc2c(c1)Cc1cnc3ccccc3c12 | c1ccc2c(c1)Cc1cnc3ccccc3c12 | Other | null | 90 | null | CN(C)CCN.O=C1c2ccccc2-c2c1c(Cl)nc1cc(F)ccc21>>CN(C)CCNc1nc2cc(F)ccc2c2c1C(=O)c1ccccc1-2.Cl.Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7a2a319b1424424183bfefb01280793f | COc1ccc2c3c(c(NCCN(C)C)nc2c1)C(=O)c1ccccc1-3>>CN(C)CCNc1nc2cc(O)ccc2c2c1C(=O)c1ccccc1-2 | CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)OC.Br>>CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)O | C[O:12][c:11]1[cH:10][c:9]2[n:8][c:7]([NH:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])[c:17]3[c:16]([c:15]2[cH:14][cH:13]1)-[c:25]1[c:20]([cH:21][cH:22][cH:23][cH:24]1)[C:18]3=[O:19]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][c:7]1[n:8][c:9]2[cH:10][c:11]([OH:12])[cH:13][cH:14][c:15]2[c:16]2[c:17]1[C:18](=[O:19])[c:20]1[cH:2... | COc1ccc2c3c(c(NCCN(C)C)nc2c1)C(=O)c1ccccc1-3 | CN(C)CCNc1nc2cc(O)ccc2c2c1C(=O)c1ccccc1-2 | null | null | C(C)(=O)O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1c2ccccc2-c2c1cnc1ccccc21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 73.2 | [{"value": 73.0, "product": "CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.2, "product": "CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-(((dimethylamino)ethyl)amino)-3-methoxy-7H-indeno[2,1-c]quinoline-7-on obtained in example 1 (3 g, 8.6 mmol) in acetic acid (40 ml) was added 47% aqueous hydrobromic acid (40 ml), and the mixture was refluxed with heat for 60 hours. The reaction mixture was distilled to dryness. To the residue was ad... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2c(c1)Cc1cnc3ccccc3c12 | Other | C(C)(=O)O | null | null | COc1ccc2c3c(c(NCCN(C)C)nc2c1)C(=O)c1ccccc1-3>C(C)(=O)O>CN(C)CCNc1nc2cc(O)ccc2c2c1C(=O)c1ccccc1-2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c99b877e128f477eb3b3215ab9fd97e9 | CC(C)(C)C(=O)Cl.CN(C)CCNc1nc2cc(O)ccc2c2c1C(=O)c1ccccc1-2>>CN(C)CCNc1nc2cc(OC(=O)C(C)(C)C)ccc2c2c1C(=O)c1ccccc1-2 | CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)O.C(C(C)(C)C)(=O)Cl.O>>CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)OC(C(C)(C)C)=O | Cl[C:13](=[O:14])[C:15]([CH3:16])([CH3:17])[CH3:18].[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][c:7]1[n:8][c:9]2[cH:10][c:11]([OH:12])[cH:19][cH:20][c:21]2[c:22]2[c:23]1[C:24](=[O:25])[c:26]1[cH:27][cH:28][cH:29][cH:30][c:31]1-2>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][c:7]1[n:8][c:9]2[cH:10][c:11]([O:12][C:13](=[O:14]... | CC(C)(C)C(=O)Cl.CN(C)CCNc1nc2cc(O)ccc2c2c1C(=O)c1ccccc1-2 | CN(C)CCNc1nc2cc(OC(=O)C(C)(C)C)ccc2c2c1C(=O)c1ccccc1-2 | null | CN(C1=CC=NC=C1)C | ClCCl | Acylation | Schotten-Baumann to ester | 1cda078f55e64d9385e544d1067595d5e7672bbd1eff542e7a341817a2d8c4d5 | 6439fc27f97ee9ed7c11ef9b5032d9493d05f28a7bbb50d256a2d54d035fbfb2 | O=C1c2ccccc2-c2c1cnc1ccccc21 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[#7;a:7]:[c:8]:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[#7;a:7]:[c:8]:[c:9]:[c:10](-[O;H0;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6]):[c:12] | 83.8 | [{"value": 80.0, "product": "CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)OC(C(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.8, "product": "CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)OC(C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 6-(((dimethylamino)ethyl)amino)-3-hydroxy-7H-indeno[2,1-c]quinoline-7-on obtained in example 3 (100 mg, 0.3 mmol) in dichloromethane (10 ml) was added 4-dimethylaminopyridine (100 mg, 0.8 mmol) and pivaloyl chloride (37 μl, 0.3 mmol), and the mixture was stirred at room temperature for 3 hours. To the ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Ester | null | null | c1ccc2c(c1)Cc1cnc3ccccc3c12 | HCl | CN(C1=CC=NC=C1)C.ClCCl | null | 3 | CC(C)(C)C(=O)Cl.CN(C)CCNc1nc2cc(O)ccc2c2c1C(=O)c1ccccc1-2>CN(C1=CC=NC=C1)C.ClCCl>CN(C)CCNc1nc2cc(OC(=O)C(C)(C)C)ccc2c2c1C(=O)c1ccccc1-2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ce23a4c71bca4f4ba6dee847e17f8171 | CN(C)CCNc1nc2cc(O)ccc2c2c1C(=O)c1ccccc1-2.O=[N+]([O-])O>>CN(C)CCNc1nc2c([N+](=O)[O-])c(O)ccc2c2c1C(=O)c1ccccc1-2 | CN(C)CCNC1=NC2=CC(=CC=C2C2=C1C(C1=CC=CC=C12)=O)O.S(O)(O)(=O)=O.[N+](=O)(O)[O-]>>CN(C)CCNC1=NC2=C(C(=CC=C2C2=C1C(C1=CC=CC=C12)=O)O)[N+](=O)[O-] | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][c:7]1[n:8][c:9]2[cH:10][c:14]([OH:15])[cH:16][cH:17][c:18]2[c:19]2[c:20]1[C:21](=[O:22])[c:23]1[cH:24][cH:25][cH:26][cH:27][c:28]1-2.O[N+:11](=[O:12])[O-:13]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][c:7]1[n:8][c:9]2[c:10]([N+:11](=[O:12])[O-:13])[c:14]([OH:15])[cH:16][cH:17][... | CN(C)CCNc1nc2cc(O)ccc2c2c1C(=O)c1ccccc1-2.O=[N+]([O-])O | CN(C)CCNc1nc2c([N+](=O)[O-])c(O)ccc2c2c1C(=O)c1ccccc1-2 | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 72df91ab04c1aa0276ed1cd35e65c268b12f156077bf94b083e8543d8aab8581 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=C1c2ccccc2-c2c1cnc1ccccc21 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H1:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8](:[c:9]):[#7;a:10]:[c:11]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:7](:[c:5](-[O;D1;H1:4]):[c:6]):[c:8](:[c:9]):[#7;a:10]:[c:11] | 52.9 | [{"value": 52.9, "product": "CN(C)CCNC1=NC2=C(C(=CC=C2C2=C1C(C1=CC=CC=C12)=O)O)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 2 | HOUR | A mixture of 6-(((dimethylamino)ethyl)amino)-3-hydroxy-7H-indeno[2,1-c]quinoline-7-on obtained in example 3 (100 mg, 0.3 mmol), conc. sulfuric acid (1 ml) and nitric acid (1 ml) was stirred at 5° C. for 2 hours. The reaction mixture was poured into ice water, and a crystal precipitated was collected by filtration. The ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2c(c1)Cc1cnc3ccccc3c12 | c1ccc2c(c1)Cc1cnc3ccccc3c12 | c1ccc2c(c1)Cc1cnc3ccccc3c12 | HO- | null | 5 | 2 | CN(C)CCNc1nc2cc(O)ccc2c2c1C(=O)c1ccccc1-2.O=[N+]([O-])O>>CN(C)CCNc1nc2c([N+](=O)[O-])c(O)ccc2c2c1C(=O)c1ccccc1-2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9d97a55e700483bba5a21fd55b4d6fd | CN(C)CCO.O=C1c2cc3c(cc2-c2c1c(Cl)nc1ccccc21)OCO3>>CN(C)CCOc1nc2ccccc2c2c1C(=O)c1cc3c(cc1-2)OCO3 | [Na].CN(CCO)C.ClC1=NC2=CC=CC=C2C2=C1C(C1=CC3=C(C=C12)OCO3)=O>>CN(CCOC1=NC2=CC=CC=C2C2=C1C(C1=CC3=C(C=C12)OCO3)=O)C | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][OH:6].Cl[c:7]1[n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[c:15]2[c:16]1[C:17](=[O:18])[c:19]1[cH:20][c:21]3[c:22]([cH:23][c:24]1-2)[O:25][CH2:26][O:27]3>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][O:6][c:7]1[n:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[c:15]2[c:16]1[C:17](=[O:18])[c:19]... | CN(C)CCO.O=C1c2cc3c(cc2-c2c1c(Cl)nc1ccccc21)OCO3 | CN(C)CCOc1nc2ccccc2c2c1C(=O)c1cc3c(cc1-2)OCO3 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 466983d8c6e1d9879bb3fee50392b4818095df00410374b9b2492c0d73b38138 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=C1c2cc3c(cc2-c2c1cnc1ccccc21)OCO3 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5])-[C:6](=[O;D1;H0:7])-[c:8].[C:9]-[C:10]-[OH;D1;+0:11]>>[C:9]-[C:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5])-[C:6](=[O;D1;H0:7])-[c:8] | 68.1 | [{"value": 68.1, "product": "CN(CCOC1=NC2=CC=CC=C2C2=C1C(C1=CC3=C(C=C12)OCO3)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.1, "product": "CN(CCOC1=NC2=CC=CC=C2C2=C1C(C1=CC3=C(C=C12)OCO3)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a solution prepared with sodium (1.78 g, 77.4 mmol) and 2-dimethylaminoethanol (80 ml, 796 mmol) was added 6-chloro-9,10-methylenedioxy-7H-indeno[2,1-c]quinoline-7-on (8 g, 25.8 mmol) obtained in reference example 2, and the mixture was stirred with heat at 60° C. for 24 hours. The reaction mixture was poured into i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccc2c(c1)ncc1c2c2cc3c(cc2C1)OCO3 | c1ccc2c(c1)ncc1c2c2cc3c(cc2C1)OCO3 | c1ccc2c(c1)ncc1c2c2cc3c(cc2C1)OCO3 | HCl | null | 60 | null | CN(C)CCO.O=C1c2cc3c(cc2-c2c1c(Cl)nc1ccccc21)OCO3>>CN(C)CCOc1nc2ccccc2c2c1C(=O)c1cc3c(cc1-2)OCO3 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8b31f28fee234e13852a8ce8d1ee7421 | CSc1ncc(C#N)c(O)n1.O=P(Cl)(Cl)Cl>>CSc1ncc(C#N)c(Cl)n1 | C(#N)C=1C(=NC(=NC1)SC)O.P(=O)(Cl)(Cl)Cl>>ClC1=NC(=NC=C1C#N)SC | O[c:9]1[c:6]([C:7]#[N:8])[cH:5][n:4][c:3]([S:2][CH3:1])[n:11]1.O=P(Cl)(Cl)[Cl:10]>>[CH3:1][S:2][c:3]1[n:4][cH:5][c:6]([C:7]#[N:8])[c:9]([Cl:10])[n:11]1 | CSc1ncc(C#N)c(O)n1.O=P(Cl)(Cl)Cl | CSc1ncc(C#N)c(Cl)n1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | c34cc3a735ba90a6ebc3a31af86c6a0085713d9dcab569055caa3b8d444bb07d | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1cncnc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4](-[#16:5]):[#7;a:6]:[c:7]:[c:8]:1-[C:9]#[N;D1;H0:10]>>[#16:5]-[c:4]1:[#7;a:3]:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[c:8](-[C:9]#[N;D1;H0:10]):[c:7]:[#7;a:6]:1 | null | [] | null | null | null | null | A mixture of 5-cyano-4-hydroxy-2-methylsulfanylpyrimidine (48.33 g) from Example 1 and phosphorus oxychloride (150 mL) was heated at reflux for 3 hours. The reaction mixture was allowed to cool to room temperature, filtered, and the filtrate was concentrated to dryness under vacuum. The residue was partitioned between ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | null | null | null | CSc1ncc(C#N)c(O)n1.O=P(Cl)(Cl)Cl>>CSc1ncc(C#N)c(Cl)n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3c865d11870445439885fc69ae3775bc | CNc1nc(NN)ncc1C#N>>CNc1nc(N=[N+]=[N-])ncc1C#N | N(=O)[O-].[Na+].C(#N)C=1C(=NC(=NC1)NN)NC.Cl>>N(=[N+]=[N-])C1=NC=C(C(=N1)NC)C#N | [CH3:1][NH:2][c:3]1[n:4][c:5]([NH:6][NH2:7])[n:9][cH:10][c:11]1[C:12]#[N:13]>>[CH3:1][NH:2][c:3]1[n:4][c:5]([N:6]=[N+:7]=[N-:8])[n:9][cH:10][c:11]1[C:12]#[N:13] | CNc1nc(NN)ncc1C#N | CNc1nc(N=[N+]=[N-])ncc1C#N | null | null | O | Functional Group Interconversion | OtherReaction | 238247da1d2da37def182788bc0f9fd914e93bf24d8f65df54deba7c01d5ce90 | fcfda441f91d6f59460078f0578a86bbab055471ecbff1b88b2ee65bf6892672 | c1cncnc1 | [NH2;D1;+0:1]-[NH;D2;+0:2]-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7]>>[N;-;D1;H0:8]=[N+;H0;D2:1]=[N;H0;D2;+0:2]-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7] | 96.8 | [{"value": 96.8, "product": "N(=[N+]=[N-])C1=NC=C(C(=N1)NC)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 20 | MINUTE | To a cold (5° C.) solution of 5-cyano-2-hydrazino-4-methylamino-pyrimidine (21.7 g) from Example 4 in a mixture of water (260 mL) and concentrated HCl (26.5 mL) was added dropwise a solution of NaNO2 (10.03 g) in water (25 mL) with overhead mechanical stirring. A white precipitate formed and after the addition was comp... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine | Azide | null | null | c1cncnc1 | null | O | 5 | 0.333333 | CNc1nc(NN)ncc1C#N>O>CNc1nc(N=[N+]=[N-])ncc1C#N |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-30431f184fdc4b00a734c5fabc99cc4f | CNc1nc(N=[N+]=[N-])ncc1C#N.O=CO>>CNc1nc(N)ncc1C=O | N(=[N+]=[N-])C1=NC=C(C(=N1)NC)C#N.C(=O)O.[H][H]>>NC1=NC=C(C(=N1)NC)C=O | N#[C:10][c:9]1[c:3]([NH:2][CH3:1])[n:4][c:5]([N:6]=[N+]=[N-])[n:7][cH:8]1.OC=[O:11]>>[CH3:1][NH:2][c:3]1[n:4][c:5]([NH2:6])[n:7][cH:8][c:9]1[CH:10]=[O:11] | CNc1nc(N=[N+]=[N-])ncc1C#N.O=CO | CNc1nc(N)ncc1C=O | null | [Ni].[Ni] | null | Miscellaneous | OtherReaction | 3353e7bb07a95f9ddc36fda04e1ee037bcb76832d7d05908a7ce09412e4bd137 | f3e2c23d9f38fc7b23dd8650cee0eab791b6ee1ce7d6cb2640cd5ee5858186e4 | c1cncnc1 | N#[C;H0;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5](-[N;H0;D2;+0:6]=[N+]=[N-]):[#7;a:7]:[c:8]:1-[#7:9].O-C=[O;H0;D1;+0:10]>>[#7:9]-[c:8]1:[#7;a:7]:[c:5](-[NH2;D1;+0:6]):[#7;a:4]:[c:3]:[c:2]:1-[CH;D2;+0:1]=[O;H0;D1;+0:10] | null | [] | null | null | 30 | MINUTE | To a suspension of 2-azido-5-cyano-4-methylaminopyrimidine (22.24 g) from Example 5 in 400 mL of 50% aqueous formic acid was added Raney Nickel catalyst (5 g). The reaction mixture was shaken under an atmosphere of hydrogen (40.1 psi) in a Parr hydrogenation apparatus. There was a vigorous evolution of gas as the mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide.Nitrile | Aldehyde.Primary amine | null | null | c1cncnc1 | Other | [Ni].[Ni] | null | 0.5 | CNc1nc(N=[N+]=[N-])ncc1C#N.O=CO>[Ni].[Ni]>CNc1nc(N)ncc1C=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c7d58afcdbc5402387de5b23c0166a3e | N#CCc1c(Cl)cccc1Cl.Nc1ncc(C=O)c(N)n1>>Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | C(C)OCC[O-].[Na+].[Na].NC1=NC=C(C(=N1)N)C=O.ClC1=C(C(=CC=C1)Cl)CC#N>>NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)N | [CH2:7]([c:8]1[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]1[Cl:15])[C:16]#[N:17].O=[CH:6][c:5]1[cH:4][n:3][c:2]([NH2:1])[n:20][c:19]1[NH2:18]>>[NH2:1][c:2]1[n:3][cH:4][c:5]2[cH:6][c:7](-[c:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[Cl:15])[c:16]([NH2:17])[n:18][c:19]2[n:20]1 | N#CCc1c(Cl)cccc1Cl.Nc1ncc(C=O)c(N)n1 | Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 | null | null | C(C)OCCO | Aromatic Heterocycle Formation | OtherReaction | 457efb65ee92bdd64de5e4c4637aa6a6f5956ef7df9875f74f905470843f8329 | ee9b166152faf84f609712c2b467526aa08715073838c269f02320595214b178 | c1ccc(-c2cnc3ncncc3c2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH2;D1;+0:8].[Cl;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[CH2;D2;+0:13]-[C;H0;D2;+0:14]#[N;H0;D1;+0:15]):[c:16](-[Cl;D1;H0:17]):[c:18]>>[Cl;D1;H0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[c;H0;D3;+0:13]1:[cH;D2;+0:1]:[c:2]2:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:... | null | [] | null | null | null | null | (Prepared by the method of U.S. Pat. No. 3,534,039). To a solution of sodium 2-ethoxyethoxide prepared from 0.14 g of sodium and 60 mL of 2-ethoxyethanol was added 2.07 g of 2,4-diamino-5-pyrimidinecarboxaldehyde, and 2.79 g of 2,6-dichlorophenylacetonitrile. The mixture was heated at reflux for 4 hours, allowed to coo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Primary amine | Primary amine | c1cncnc1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | HO- | C(C)OCCO | null | null | N#CCc1c(Cl)cccc1Cl.Nc1ncc(C=O)c(N)n1>C(C)OCCO>Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(N)nc2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6e29f6338ec248b690e8a6491c1779c2 | CI.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(O)nc2n1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | [H-].[Na+].NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)O.CI>>NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)C | I[CH3:1].[n:2]1[c:3]([OH:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2[cH:16][n:17][c:18]([NH2:19])[n:20][c:21]12>>[CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2[cH:16][n:17][c:18]([NH2:19])[n:20][c:21]12 | CI.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(O)nc2n1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | null | null | CN(C=O)C | Acylation | OtherReaction | 7dd5a2fccb6323a5f77a4b63756fc3de8ac3d3fad89bb5d6740eb97207c75fcc | 112bab89a832807e83a4911f32b3895489765458263eca889524c8ed19f7b9da | O=c1[nH]c2ncncc2cc1-c1ccccc1 | I-[CH3;D1;+0:1].[OH;D1;+0:2]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:2:[c:11]:[c:12]:1-[c:13]>>[CH3;D1;+0:1]-[n;H0;D3;+0:4]1:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:2:[c:11]:[c:12](-[c:13]):[c;H0;D3;+0:3]:1=[O;H0;D1;+0:2] | 49.1 | [{"value": 49.1, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 3 | HOUR | To a mixture of 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7-ol (3.7 g) from Example 11 in dimethylformamide was added NaH (50% suspension in mineral oil, 0.64 g). The resulting slurry was heated at 65° C. for 0.5 hour until a solution formed. It was then cooled to 50° C. and a solution of methyl iodide (2.0... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | null | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1 | HI | CN(C=O)C | 65 | 3 | CI.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(O)nc2n1>CN(C=O)C>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f8431548c7b24ab7baaa89a876f8af64 | Cc1ccccc1-c1cc2cnc(N)nc2n(C)c1=N.O>>Cc1ccccc1-c1cc2cnc(N)nc2n(C)c1=O | CC1=C(C=CC=C1)C1=CC2=C(N=C(N=C2)N)N(C1=N)C.Cl.O>>NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2)C)=O)C | N=[c:19]1[c:8](-[c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]2)[cH:9][c:10]2[cH:11][n:12][c:13]([NH2:14])[n:15][c:16]2[n:17]1[CH3:18].[OH2:20]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][c:10]2[cH:11][n:12][c:13]([NH2:14])[n:15][c:16]2[n:17]([CH3:18])[c:19]1=[O:20] | Cc1ccccc1-c1cc2cnc(N)nc2n(C)c1=N.O | Cc1ccccc1-c1cc2cnc(N)nc2n(C)c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 7e90239cfce707b5d71d7acd2c9920e6ba1c56c90bac03a2d6d5e6e8da49f59b | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | O=c1[nH]c2ncncc2cc1-c1ccccc1 | N=[c;H0;D3;+0:1]1:[#7;a:2](-[C;D1;H3:3]):[c:4]2:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[c:10]:[c:11]:1-[c:12].[OH2;D0;+0:13]>>[C;D1;H3:3]-[#7;a:2]1:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[c:10]:[c:11](-[c:12]):[c;H0;D3;+0:1]:1=[O;H0;D1;+0:13] | null | [] | null | null | null | null | To a mixture of 6-(2-methylphenyl)-7-imino-8-methyl-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamine (0.30 g) from Example 8 and concentrated HCl (0.6 mL) was added water (11 mL). The reaction mixture was refluxed for 20 hours, then allowed to cool to room temperature. The white precipitate from the reaction mixture was fi... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1 | Other | null | null | null | Cc1ccccc1-c1cc2cnc(N)nc2n(C)c1=N.O>>Cc1ccccc1-c1cc2cnc(N)nc2n(C)c1=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-040121136d37435a8bcc1f1ef88ef22c | CC(=O)OC(C)=O.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21>>CC(=O)Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)C.C(C)(=O)OC(C)=O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC(C)=O)N(C1=O)C | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[n:6][cH:7][c:8]2[cH:9][c:10](-[c:11]3[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]3[Cl:18])[c:19](=[O:20])[n:21]([CH3:22])[c:23]2[n:24]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][cH:7][c:8]2[cH:9][c:10](-[c:11]3[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]3[Cl:18])[c:19](=[O:20])[n:21](... | CC(=O)OC(C)=O.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | CC(=O)Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | null | null | null | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | O=c1[nH]c2ncncc2cc1-c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]:[c:5]:[#7;a:6]:[c:7](-[NH2;D1;+0:8]):[#7;a:9]:[c:10]>>[#7;a:4]:[c:5]:[#7;a:6]:[c:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[#7;a:9]:[c:10] | null | [] | 25 | CELSIUS | null | null | A mixture of 64.2 mg (0.20 mmol) of 2-amino-6-(2,6-dichlorophenyl)-8-methyl-pyrido[2,3-d]pyrimidin-7(8H)-one (from Example 12) and 1 mL of acetic anhydride was heated to reflux. The resulting solution was maintained at reflux for 20 minutes and concentrated at atmospheric pressure to about 0.25 mL volume. The solution ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1cnc2ncncc2c1.c1ccccc1 | HO- | null | 25 | null | CC(=O)OC(C)=O.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21>>CC(=O)Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7f755484eae34b89a6dc4eb4bf6a4b14 | CNc1nc(SC)ncc1C#N.O>>CNc1nc(SC)ncc1C=O | C(#N)C=1C(=NC(=NC1)SC)NC.O>>CNC1=NC(=NC=C1C=O)SC | N#[C:11][c:10]1[c:3]([NH:2][CH3:1])[n:4][c:5]([S:6][CH3:7])[n:8][cH:9]1.[OH2:12]>>[CH3:1][NH:2][c:3]1[n:4][c:5]([S:6][CH3:7])[n:8][cH:9][c:10]1[CH:11]=[O:12] | CNc1nc(SC)ncc1C#N.O | CNc1nc(SC)ncc1C=O | null | null | C(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 26082e4725cd2a7c1eb6362fc44981286c2087c015aba2f1b570103659ffb41e | e783d65987caa6ceae095ff666413e4c8d25ead96c003eb4f99d66fc68c0b0bb | c1cncnc1 | N#[C;H0;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[#7:8].[OH2;D0;+0:9]>>[#7:8]-[c:7]1:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:1-[CH;D2;+0:1]=[O;H0;D1;+0:9] | null | [] | 25 | CELSIUS | 12 | HOUR | A solution of 4.00 g (0.022 mol) of 5-cyano-4-methylamino-2-methylsulfanyl-pyrimidine (from Example 3) in 150 mL of 50% aqueous formic acid was reacted with 6.0 g of water-wet Raney Nickel. The mixture was stirred at 25° C. for 12 hours. The solids were filtered and washed with 40 mL of 50% aqueous formic acid. With ic... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Aldehyde | null | null | c1cncnc1 | Other | C(=O)O | 25 | 12 | CNc1nc(SC)ncc1C#N.O>C(=O)O>CNc1nc(SC)ncc1C=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dd5613fe644d4335b125576fcb33212e | CCOC(=O)c1cnc(SC)nc1Cl.CN>>CCOC(=O)c1cnc(SC)nc1NC | CN.C(C)OC(=O)C=1C(=NC(=NC1)SC)Cl.C(C)N(CC)CC>>C(C)OC(=O)C=1C(=NC(=NC1)SC)NC | Cl[c:13]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][n:8][c:9]([S:10][CH3:11])[n:12]1.[NH2:14][CH3:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([S:10][CH3:11])[n:12][c:13]1[NH:14][CH3:15] | CCOC(=O)c1cnc(SC)nc1Cl.CN | CCOC(=O)c1cnc(SC)nc1NC | null | null | CCCCCC.O1CCCC1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[C;D1;H3:12]-[NH2;D1;+0:13]>>[#16:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:13]-[C;D1;H3:12]):[c:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]):[c:6]:[#7;a:5]:1 | 81 | [{"value": 81.0, "product": "C(C)OC(=O)C=1C(=NC(=NC1)SC)NC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.4, "product": "C(C)OC(=O)C=1C(=NC(=NC1)SC)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 30 | MINUTE | To a solution of 4-chloro-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester (18.66 g, 80.4 mmol) in 260 mL of tetrahydrofuran was added triethylamine (34 mL, 244 mmol), followed by 30 mL of a 40% aqueous solution of methylamine. The solution was stirred for 30 minutes at 25° C. then concentrated in vacuo and partiti... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | CCCCCC.O1CCCC1 | 25 | 0.5 | CCOC(=O)c1cnc(SC)nc1Cl.CN>CCCCCC.O1CCCC1>CCOC(=O)c1cnc(SC)nc1NC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-abfc9b5568f94a61bc5a0e552cd345d3 | CCOC(=O)c1cnc(SC)nc1NC>>CNc1nc(SC)ncc1CO | C(C)OC(=O)C=1C(=NC(=NC1)SC)NC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>CNC1=NC(=NC=C1CO)SC | CCO[C:11]([c:10]1[c:3]([NH:2][CH3:1])[n:4][c:5]([S:6][CH3:7])[n:8][cH:9]1)=[O:12]>>[CH3:1][NH:2][c:3]1[n:4][c:5]([S:6][CH3:7])[n:8][cH:9][c:10]1[CH2:11][OH:12] | CCOC(=O)c1cnc(SC)nc1NC | CNc1nc(SC)ncc1CO | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1cncnc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[#7:9]>>[#7:9]-[c:8]1:[#7;a:7]:[c:6]:[#7;a:5]:[c:4]:[c:3]:1-[CH2;D2;+0:1]-[OH;D1;+0:2] | 84 | [{"value": 84.0, "product": "CNC1=NC(=NC=C1CO)SC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.6, "product": "CNC1=NC(=NC=C1CO)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 4-methylamino-2-methylsulfanyl-5-pyrimidinecarboxylate ethyl ester (4.36 g, 19.3 mmol) in 60 mL of tetrahydrofuran was added dropwise to a room temperature suspension of lithium aluminum hydride (1.10 g, 29.0 mmol) in 40 mL of tetrahydrofuran. After 10 minutes the reaction was carefully quenched with 2 mL... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cncnc1 | HO- | O1CCCC1 | null | 1 | CCOC(=O)c1cnc(SC)nc1NC>O1CCCC1>CNc1nc(SC)ncc1CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8aa336f790624ad587b9c64aa9340829 | CNc1nc(SC)ncc1CO>>CNc1nc(SC)ncc1C=O | CNC1=NC(=NC=C1CO)SC.O.O.[Cr](=O)(=O)([O-])O[Cr](=O)(=O)[O-].[Na+].[Na+].O.O.[Cr](=O)(=O)([O-])O[Cr](=O)(=O)[O-].[Na+].[Na+]>>CNC1=NC(=NC=C1C=O)SC | [CH3:1][NH:2][c:3]1[n:4][c:5]([S:6][CH3:7])[n:8][cH:9][c:10]1[CH2:11][OH:12]>>[CH3:1][NH:2][c:3]1[n:4][c:5]([S:6][CH3:7])[n:8][cH:9][c:10]1[CH:11]=[O:12] | CNc1nc(SC)ncc1CO | CNc1nc(SC)ncc1C=O | null | null | C(C)(=O)O | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1cncnc1 | [#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH2;D2;+0:8]-[OH;D1;+0:9]>>[#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH;D2;+0:8]=[O;H0;D1;+0:9] | 30.2 | [{"value": 30.0, "product": "CNC1=NC(=NC=C1C=O)SC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.2, "product": "CNC1=NC(=NC=C1C=O)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 4-Methylamino-2-methylsulfanyl-5-pyrimidine-methanol (2.40 g, 13.0 mmol) in 7 mL of acetic acid was added to a solution of sodium dichromate-dihydrate (1.30 g, 4.4 mmol) in 6 mL of acetic acid. After 2 hours at room temperature, additional sodium dichromate-dihydrate (0.3 g, 1.0 mmol) in 1 mL of acetic acid was added. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cncnc1 | null | C(C)(=O)O | null | 2 | CNc1nc(SC)ncc1CO>C(C)(=O)O>CNc1nc(SC)ncc1C=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a7d5dc196a1f4db59fce7d32888d8b45 | CNc1nc(SC)ncc1C=O.N#CCc1c(Cl)cccc1Cl>>CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=N)n(C)c2n1 | C(C)(=O)OCC.C([O-])([O-])=O.[K+].[K+].CNC1=NC(=NC=C1C=O)SC.ClC1=C(C(=CC=C1)Cl)CC#N.CN(C=O)C>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=N)C | O=[CH:7][c:6]1[cH:5][n:4][c:3]([S:2][CH3:1])[n:22][c:21]1[NH:19][CH3:20].[CH2:8]([c:9]1[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]1[Cl:16])[C:17]#[N:18]>>[CH3:1][S:2][c:3]1[n:4][cH:5][c:6]2[cH:7][c:8](-[c:9]3[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]3[Cl:16])[c:17](=[NH:18])[n:19]([CH3:20])[c:21]2[n:22]1 | CNc1nc(SC)ncc1C=O.N#CCc1c(Cl)cccc1Cl | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=N)n(C)c2n1 | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 0563001d31884c03e15e9f4307d31ffde7ef37fabfd8267db28237eb39076249 | 869483589005a5aba7d1617b2e2f826aa2ded09152e8d61d0607fd18c3c9c8b9 | N=c1[nH]c2ncncc2cc1-c1ccccc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[NH;D2;+0:8]-[C;D1;H3:9].[Cl;D1;H0:10]-[c:11](:[c:12]):[c;H0;D3;+0:13](-[CH2;D2;+0:14]-[C;H0;D2;+0:15]#[N;H0;D1;+0:16]):[c:17](-[Cl;D1;H0:18]):[c:19]>>[C;D1;H3:9]-[n;H0;D3;+0:8]1:[c:7]2:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:[c:2]:2:[cH;D2;+0:1]:[c;H0;D3;+0:14](-[c;H0;... | 40 | [{"value": 40.0, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=N)C", "details": "PERCENTYIELD", "is_desired": false}] | 125 | CELSIUS | 6 | HOUR | Powdered potassium carbonate (0.8 g; 5.8 mmol) was added to a solution of 0.220 g (1.2 mmol) of the aldehyde from Example 18 and 0.235 g (1.26 mmol) (ca. 5% excess) of 2,6-dichlorophenylacetonitrile in 2.0 mL of dimethylformamide. The mixture was heated with stirring at 125° C. for 6 hours. Ethyl acetate (5 mL) was add... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Secondary amine | null | c1cncnc1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | HO- | C(Cl)Cl | 125 | 6 | CNc1nc(SC)ncc1C=O.N#CCc1c(Cl)cccc1Cl>C(Cl)Cl>CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=N)n(C)c2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-35741f9734764022a52b0d43501cf256 | CCOCCOc1ncc2cc(-c3c(Cl)cccc3Cl)c(=N)n(C)c2n1>>Cl.Cn1c(=N)c(-c2c(Cl)cccc2Cl)cc2cnc(O)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)OCCOCC)N(C1=N)C>>Cl.ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)O)N(C1=N)C | CCOCC[O:20][c:19]1[n:18][cH:17][c:16]2[cH:15][c:6](-[c:7]3[c:8]([Cl:1])[cH:10][cH:11][cH:12][c:13]3[Cl:14])[c:4](=[NH:5])[n:3]([CH3:2])[c:22]2[n:21]1>>[ClH:1].[CH3:2][n:3]1[c:4](=[NH:5])[c:6](-[c:7]2[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]2[Cl:14])[cH:15][c:16]2[cH:17][n:18][c:19]([OH:20])[n:21][c:22]12 | CCOCCOc1ncc2cc(-c3c(Cl)cccc3Cl)c(=N)n(C)c2n1 | Cl.Cn1c(=N)c(-c2c(Cl)cccc2Cl)cc2cnc(O)nc21 | null | null | Cl | Miscellaneous | OtherReaction | b4cea5b2d239b73e5c5aee3137cdaad3b3f8aa211f3a34a1cea4e9dd11de1feb | c427c467a576ca94eabe2e08bd6347a4b9bbc0385f3c9122178b52dbe50a75a3 | N=c1[nH]c2ncncc2cc1-c1ccccc1 | C-C-O-C-C-[O;H0;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](-[Cl;H0;D1;+0:13]):[c:14]:[c:15]>>[Cl;D1;H0:16]-[c;H0;D3;+0:12](:[c:14]:[c:15]):[c:10](-[c:9]:[c:8]:[#7;a:7]:[c:6]:[#7;a:5]:[c:2](-[OH;D1;+0:1]):[#7;a:3]:[c:4]):[c:11].[ClH;D0;+0:13] | null | [] | null | null | null | null | A solution of 78.0 mg (0.20 mmol) of the ethoxyethyl ether from Example 22 in 1.0 mL of 6N hydrochloric acid was heated at reflux for 5 minutes. The solvent was removed by evaporation under reduced pressure. The remaining solid hydrochloride salt was recrystallized from ethanol-ethyl acetate to afford crystalline 6-(2,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether | Aromatic halide.Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cnc2ncncc2c1 | HO- | Cl | null | null | CCOCCOc1ncc2cc(-c3c(Cl)cccc3Cl)c(=N)n(C)c2n1>Cl>Cl.Cn1c(=N)c(-c2c(Cl)cccc2Cl)cc2cnc(O)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9cc63b0f6a514bce8d35b9f03404b410 | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21>>Cn1c(=S)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)C.COC=1C=CC(=CC1)P2(=S)SP(=S)(S2)C=3C=CC(=CC3)OC>>NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=S)C | COc1ccc(P2(=S)SP(c3ccc(OC)cc3)(=[S:4])S2)cc1.O=[c:3]1[n:2]([CH3:1])[c:21]2[c:15]([cH:14][c:5]1-[c:6]1[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]1[Cl:13])[cH:16][n:17][c:18]([NH2:19])[n:20]2>>[CH3:1][n:2]1[c:3](=[S:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2[cH:16][n:17][c:18]([NH2:19])[n:... | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | Cn1c(=S)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | cffb02ee009c6075673bb4ccc2b6ab6758ccd066ab0e544ca5420e501c92747c | 6988b5bdf4783315bb3059677289ee20aff4c88fbf4684f4ee12b75839fcb0a0 | S=c1[nH]c2ncncc2cc1-c1ccccc1 | C-O-c1:c:c:c(-P2(=S)-S-P(=[S;H0;D1;+0:1])(-c3:c:c:c(-O-C):c:c:3)-S-2):c:c:1.O=[c;H0;D3;+0:2](:[#7;a:3](-[C;D1;H3:4]):[c:5]:[#7;a:6]):[c:7](-[c:8]):[c:9]>>[#7;a:6]:[c:5]:[#7;a:3](-[C;D1;H3:4]):[c;H0;D3;+0:2](=[S;H0;D1;+0:1]):[c:7](-[c:8]):[c:9] | null | [] | null | null | 24 | HOUR | A mixture of 0.321 g (1.0 mmol) of 2-amino-6-(2,6-dichlorophenyl)-8-methyl-pyrido[2,3-d]pyrimidin-7-(8H)-one from Example 12 and 0.404 g (1.0 mmol) of Lawesson's Reagent in 10 mL of pyridine was heated at reflux with stirring for 24 hours. The solvent was evaporated under reduced pressure, and the residue was triturate... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Monosulfide.Monosulfide | Thiocarbonyl | c1ccccc1.P1SPS1.c1ccccc1.c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1 | Other | N1=CC=CC=C1 | null | 24 | COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21>N1=CC=CC=C1>Cn1c(=S)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-de9b6ae759eb4e73bdbda8a0c8140fe5 | CC(=O)OC(C)=O.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=N)n(C)c2n1>>CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=NC(C)=O)n(C)c2n1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=N)C.C(C)(=O)OC(C)=O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=NC(C)=O)C | CC(=O)O[C:19]([CH3:20])=[O:21].[CH3:1][S:2][c:3]1[n:4][cH:5][c:6]2[cH:7][c:8](-[c:9]3[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]3[Cl:16])[c:17](=[NH:18])[n:22]([CH3:23])[c:24]2[n:25]1>>[CH3:1][S:2][c:3]1[n:4][cH:5][c:6]2[cH:7][c:8](-[c:9]3[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]3[Cl:16])[c:17](=[N:18][C:19]([CH3:20])=... | CC(=O)OC(C)=O.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=N)n(C)c2n1 | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=NC(C)=O)n(C)c2n1 | null | null | CCOCC | Acylation | Aminolysis of esters | 868ba94f028b30e9347f1568001d166d126ab48ad34862bd252bb72f87967edd | 93289da630dbaf2d9339c4212dcd342dfbcc29df4e79a63418a0fd9f589abdc1 | N=c1[nH]c2ncncc2cc1-c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]:[c:5]:[#7;a:6](-[C;D1;H3:7]):[c:8](=[NH;D1;+0:9]):[c:10]>>[#7;a:4]:[c:5]:[#7;a:6](-[C;D1;H3:7]):[c:8](=[N;H0;D2;+0:9]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:10] | null | [] | null | null | null | null | A mixture of 0.161 g (0.46 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3 -d]pyrimidin-7-ylideneamine from Example 19 and 1.0 mL of acetic anhydride was heated to solution at the boiling point. After 2 minutes of reflux, the solution was concentrated to one-half volume, whereupon crystals forme... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | null | null | null | c1cnc2ncncc2c1.c1ccccc1 | HO- | CCOCC | null | null | CC(=O)OC(C)=O.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=N)n(C)c2n1>CCOCC>CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=NC(C)=O)n(C)c2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dc089cf7000c4b12a70b5ffd130e6b36 | CCI.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(O)nc2n1>>CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)O.[H-].[Na+].C(C)I>>NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC | I[CH2:2][CH3:1].[n:3]1[c:4]([OH:5])[c:6](-[c:7]2[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]2[Cl:14])[cH:15][c:16]2[cH:17][n:18][c:19]([NH2:20])[n:21][c:22]12>>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6](-[c:7]2[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]2[Cl:14])[cH:15][c:16]2[cH:17][n:18][c:19]([NH2:20])[n:21][c:22]12 | CCI.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(O)nc2n1 | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | null | null | CN(C=O)C | Acylation | OtherReaction | d4508e77261150488c4c1380432c15a2d90e999afdd39fb804eb30619cd6fa28 | 1ace3814128badf62d481904cb0fc2463e51f1c5bfb35fa1f883a03bb843d915 | O=c1[nH]c2ncncc2cc1-c1ccccc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[OH;D1;+0:3]-[c;H0;D3;+0:4]1:[n;H0;D2;+0:5]:[c:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:2:[c:12]:[c:13]:1-[c:14]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:5]1:[c:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:2:[c:12]:[c:13](-[c:14]):[c;H0;D3;+0:4]:1=[O;H0;D1;+0:3] | 55.4 | [{"value": 55.0, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.4, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 3.5 | HOUR | To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (172 mg, 0.56 mmol) from Example 11. The mixture was heated at 50° C. for 1 hour resulting in a clear solution. Ethyl iodide (60 μL, 0.75 mmol) was added, and the sol... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | null | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1 | HI | CN(C=O)C | 50 | 3.5 | CCI.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(O)nc2n1>CN(C=O)C>CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e91dd296e2224593a86fc92fbc509e8b | CCCI.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(O)nc2n1>>CCCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | NC=1N=CC2=C(N1)N=C(C(=C2)C2=C(C=CC=C2Cl)Cl)O.[H-].[Na+].ICCC>>NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CCC | I[CH2:3][CH2:2][CH3:1].[n:4]1[c:5]([OH:6])[c:7](-[c:8]2[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]2[Cl:15])[cH:16][c:17]2[cH:18][n:19][c:20]([NH2:21])[n:22][c:23]12>>[CH3:1][CH2:2][CH2:3][n:4]1[c:5](=[O:6])[c:7](-[c:8]2[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]2[Cl:15])[cH:16][c:17]2[cH:18][n:19][c:20]([NH2:21])[n:22][c:2... | CCCI.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(O)nc2n1 | CCCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | null | null | CN(C=O)C | Acylation | OtherReaction | d4508e77261150488c4c1380432c15a2d90e999afdd39fb804eb30619cd6fa28 | 1ace3814128badf62d481904cb0fc2463e51f1c5bfb35fa1f883a03bb843d915 | O=c1[nH]c2ncncc2cc1-c1ccccc1 | I-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[OH;D1;+0:4]-[c;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[c:7]2:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[c:13]:[c:14]:1-[c:15]>>[C;D1;H3:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:6]1:[c:7]2:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[c:13]:[c:14](-[c:15]):[c;H0;D3;+0:5]:1=[O;H0;D1;+0:4] | 68 | [{"value": 68.0, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.0, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 10 | MINUTE | To a suspension of NaH (60% in mineral oil, 31 mg) in 6 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one from Example 11 (205 mg, 0.67 mmol). The mixture was heated at 50° C. for 1 hour resulting in a clear solution. 1-Iodopropane (100 μL, 1.03 mmol) was added, and the s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | null | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1 | HI | CN(C=O)C | 50 | 0.166667 | CCCI.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(O)nc2n1>CN(C=O)C>CCCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-01a5e0a168094896bccae2b3b8ee6758 | CCCCI.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>>CCCCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | NC=1N=CC2=C(N1)NC(C(=C2)C2=C(C=CC=C2Cl)Cl)=O.[H-].[Na+].ICCCC>>NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CCCC | I[CH2:4][CH2:3][CH2:2][CH3:1].[nH:5]1[c:6](=[O:7])[c:8](-[c:9]2[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]2[Cl:16])[cH:17][c:18]2[cH:19][n:20][c:21]([NH2:22])[n:23][c:24]12>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6](=[O:7])[c:8](-[c:9]2[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]2[Cl:16])[cH:17][c:18]2[cH:19][n:20][c:21]([N... | CCCCI.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1 | CCCCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c0bd97f4a1ce12437e73bb376c2b79161100c8750c084a20105c044989ac3551 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c2ncncc2cc1-c1ccccc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[c:5](:[c:6]):[nH;D2;+0:7]:[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:7](:[c:8]1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:[c:13]:1):[c:5](=[O;D1;H0:4]):[c:6] | 64 | [{"value": 64.0, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.4, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 30 | MINUTE | To a suspension of NaH (60% in mineral oil, 34 mg) in 6 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (202 mg, 0.66 mmol). The mixture was heated to 50° C., resulting in a clear solution. 1-Iodobutane (105 μL, 0.92 mmol) was added, and the solution was stirred at 50° ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1 | HI | CN(C=O)C | 50 | 0.5 | CCCCI.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>CN(C=O)C>CCCCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-398313438a35477a99dae3e5237c331e | CC(C)CI.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>>CC(C)Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | ICC(C)C.[H-].[Na+].NC=1N=CC2=C(N1)NC(C(=C2)C2=C(C=CC=C2Cl)Cl)=O.ICC(C)C>>NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC(C)C | I[CH2:4][CH:2]([CH3:1])[CH3:3].[nH:5]1[c:6](=[O:7])[c:8](-[c:9]2[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]2[Cl:16])[cH:17][c:18]2[cH:19][n:20][c:21]([NH2:22])[n:23][c:24]12>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[c:6](=[O:7])[c:8](-[c:9]2[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]2[Cl:16])[cH:17][c:18]2[cH:19][n:20][c:21](... | CC(C)CI.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1 | CC(C)Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | c0bd97f4a1ce12437e73bb376c2b79161100c8750c084a20105c044989ac3551 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c2ncncc2cc1-c1ccccc1 | I-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4].[O;D1;H0:5]=[c:6](:[c:7]):[nH;D2;+0:8]:[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])-[CH2;D2;+0:1]-[n;H0;D3;+0:8](:[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1):[c:6](=[O;D1;H0:5]):[c:7] | 51 | [{"value": 51.0, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.5, "product": "NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)CC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 30 | MINUTE | To a suspension of NaH (60% in mineral oil, 36 mg) in 8 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (205 mg, 0.67 mmol). The mixture was heated at 60° C. for 20 minutes resulting in a clear solution. 1-Iodo-2-methylpropane (110 μL, 0.94 mmol) was added, and the solu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1 | HI | CN(C=O)C | 60 | 0.5 | CC(C)CI.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>CN(C=O)C>CC(C)Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-db033153fe46420cb6ff2af2382ca19e | COC(=O)CCl.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>>COC(=O)Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | NC=1N=CC2=C(N1)NC(C(=C2)C2=C(C=CC=C2Cl)Cl)=O.[H-].[Na+].ClCC(=O)OC>>COC(CN1C(C(=CC2=C1N=C(N=C2)N)C2=C(C=CC=C2Cl)Cl)=O)=O | Cl[CH2:5][C:3]([O:2][CH3:1])=[O:4].[nH:6]1[c:7](=[O:8])[c:9](-[c:10]2[c:11]([Cl:12])[cH:13][cH:14][cH:15][c:16]2[Cl:17])[cH:18][c:19]2[cH:20][n:21][c:22]([NH2:23])[n:24][c:25]12>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][n:6]1[c:7](=[O:8])[c:9](-[c:10]2[c:11]([Cl:12])[cH:13][cH:14][cH:15][c:16]2[Cl:17])[cH:18][c:19]2[cH:20][n:2... | COC(=O)CCl.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1 | COC(=O)Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | fd5ba1af7389d33cca767aae97db8ad46db379d13a808cd30e0289a97675ed04 | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | O=c1[nH]c2ncncc2cc1-c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[O;D1;H0:6]=[c:7](:[c:8]):[nH;D2;+0:9]:[c:10]1:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[n;H0;D3;+0:9](:[c:10]1:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1):[c:7](=[O;D1;H0:6]):[c:8] | 61 | [{"value": 61.0, "product": "COC(CN1C(C(=CC2=C1N=C(N=C2)N)C2=C(C=CC=C2Cl)Cl)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.7, "product": "COC(CN1C(C(=CC2=C1N=C(N=C2)N)C2=C(C=CC=C2Cl)Cl)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 38 mg) in 6 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (203 mg, 0.66 mmol). The mixture was heated at 50° C. for 40 minutes resulting in a clear solution. Methyl chloroacetate (90 μL, 1.03 mmol) was added, and the solutio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1 | HCl | CN(C=O)C | 50 | null | COC(=O)CCl.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>CN(C=O)C>COC(=O)Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-16c20da4564840b98de831447344a71e | CC(C)(C)OC(=O)CBr.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>>CC(C)(C)OC(=O)Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | NC=1N=CC2=C(N1)NC(C(=C2)C2=C(C=CC=C2Cl)Cl)=O.[H-].[Na+].BrCC(=O)OC(C)(C)C>>C(C)(C)(C)OC(CN1C(C(=CC2=C1N=C(N=C2)N)C2=C(C=CC=C2Cl)Cl)=O)=O | Br[CH2:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[nH:9]1[c:10](=[O:11])[c:12](-[c:13]2[c:14]([Cl:15])[cH:16][cH:17][cH:18][c:19]2[Cl:20])[cH:21][c:22]2[cH:23][n:24][c:25]([NH2:26])[n:27][c:28]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][n:9]1[c:10](=[O:11])[c:12](-[c:13]2[c:14]([Cl:15])[cH:16][c... | CC(C)(C)OC(=O)CBr.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1 | CC(C)(C)OC(=O)Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Boc amine protection (ethyl Boc) | fd5ba1af7389d33cca767aae97db8ad46db379d13a808cd30e0289a97675ed04 | 6007d70cc3173f3039a472489995dad2781e8d749be1f1aa209b0bf2f190a4b4 | O=c1[nH]c2ncncc2cc1-c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[O;D1;H0:9]=[c:10](:[c:11]):[nH;D2;+0:12]:[c:13]1:[#7;a:14]:[c:15]:[#7;a:16]:[c:17]:[c:18]:1>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[n;H0;D3;+0:12](:[c:10](=[O;D1;H0:9]):[c:11]):[c:... | 30.1 | [{"value": 30.0, "product": "C(C)(C)(C)OC(CN1C(C(=CC2=C1N=C(N=C2)N)C2=C(C=CC=C2Cl)Cl)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.1, "product": "C(C)(C)(C)OC(CN1C(C(=CC2=C1N=C(N=C2)N)C2=C(C=CC=C2Cl)Cl)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a suspension of NaH (60% in mineral oil, 67 mg) in 10 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (398 mg, 1.30 mmol). The mixture was heated at 45° C. to 55° C. for 40 minutes resulting in a clear solution. Tert-butyl bromoacetate (250 μL, 1.69 mmol) was added, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1 | HBr | CN(C=O)C | 50 | null | CC(C)(C)OC(=O)CBr.Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)[nH]c2n1>CN(C=O)C>CC(C)(C)OC(=O)Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(N)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bfb87e53646f4c08bf6331ebf2a578a0 | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.O=C(OO)c1cccc(Cl)c1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21 | ClC1=CC(=CC=C1)C(=O)OO.ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=O)C.CS(=O)C>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)C | [CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2[cH:16][n:17][c:18]([S:19][CH3:20])[n:23][c:24]12.Clc1cccc(C(O[OH:22])=[O:21])c1>>[CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2[cH:16][n:17][c:18]([S:19]([CH3:20])... | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.O=C(OO)c1cccc(Cl)c1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21 | null | null | C(Cl)(Cl)Cl | Oxidation | OtherReaction | 84855dd3f46d7f633669ce7b0a2d1343353729d5975dd53fd20abc6eb43ece69 | dc6f43112eef310adb122ebf81e1733b34eff292ed27058fb45445842d61d3da | O=c1[nH]c2ncncc2cc1-c1ccccc1 | Cl-c1:c:c:c:c(-C(=[O;H0;D1;+0:1])-O-[OH;D1;+0:2]):c:1.[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[S;H0;D2;+0:7]-[C;D1;H3:8]):[#7;a:9]:[c:10]>>[#7;a:3]:[c:4]:[#7;a:5]:[c:6](-[S;H0;D4;+0:7](-[C;D1;H3:8])(=[O;H0;D1;+0:1])=[O;H0;D1;+0:2]):[#7;a:9]:[c:10] | null | [] | null | null | 8 | HOUR | A quantity of 0.346 g (1.00 mmol) of 50% to 60% m-chloroperbenzoic acid (assuming 50% peracid was present) was added at 25° C. to a stirred solution of 0.165 g (0.47 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37 in 15 mL of chloroform, and the solution was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfone | c1ccccc1 | null | c1ccccc1.c1cnc2ncncc2c1 | HCl | C(Cl)(Cl)Cl | null | 8 | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.O=C(OO)c1cccc(Cl)c1>C(Cl)(Cl)Cl>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a1fc3fad89df44fb9dcbd57241fd99a3 | CN.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>>CNc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=O)C.CN>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC)N(C1=O)C | [CH3:1][NH2:2].CS[c:3]1[n:4][cH:5][c:6]2[cH:7][c:8](-[c:9]3[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]3[Cl:16])[c:17](=[O:18])[n:19]([CH3:20])[c:21]2[n:22]1>>[CH3:1][NH:2][c:3]1[n:4][cH:5][c:6]2[cH:7][c:8](-[c:9]3[c:10]([Cl:11])[cH:12][cH:13][cH:14][c:15]3[Cl:16])[c:17](=[O:18])[n:19]([CH3:20])[c:21]2[n:22]1 | CN.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | CNc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | df9d6a54bbeb74919f9913aad742e0b7c3ffefcaa8d2bb485e4914ba80c410ee | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=c1[nH]c2ncncc2cc1-c1ccccc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[c:4]:[c:5]:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[C;D1;H3:10]-[NH2;D1;+0:11]>>[C;D1;H3:10]-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[c:4]:[c:5]:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9] | null | [] | null | null | 10 | MINUTE | A quantity of 0.165 g (0.47 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37 was placed in a pressure tube with a magnetic stirring bar. The tube was cooled in a dry ice-acetone bath and ca. 3 mL of monomethylamine gas was condensed in the tube. Dimethylformamide (... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | Other | CN(C=O)C | null | 0.166667 | CN.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>CN(C=O)C>CNc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3649f27493174d968301ce7cf9e817e4 | CNC.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>>CN(C)c1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=O)C.CNC>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)N(C)C)N(C1=O)C | [CH3:1][NH:2][CH3:3].CS[c:4]1[n:5][cH:6][c:7]2[cH:8][c:9](-[c:10]3[c:11]([Cl:12])[cH:13][cH:14][cH:15][c:16]3[Cl:17])[c:18](=[O:19])[n:20]([CH3:21])[c:22]2[n:23]1>>[CH3:1][N:2]([CH3:3])[c:4]1[n:5][cH:6][c:7]2[cH:8][c:9](-[c:10]3[c:11]([Cl:12])[cH:13][cH:14][cH:15][c:16]3[Cl:17])[c:18](=[O:19])[n:20]([CH3:21])[c:22]2[n:... | CNC.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | CN(C)c1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b04bf65d5ddea11036a7e6dd1f319b06acbc4399e4bf7e6a83cd4e2648a53efe | f5aa33108984aad43441754644c214239e577e2035dc027b4aa13ab85821a21b | O=c1[nH]c2ncncc2cc1-c1ccccc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[c:4]:[c:5]:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[C;D1;H3:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C;D1;H3:10]-[N;H0;D3;+0:11](-[C;D1;H3:12])-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[c:4]:[c:5]:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9] | null | [] | null | null | null | null | This compound was prepared by a procedure similar to that described in Example 40 starting with 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37 and dimethylamine gas; mp 256°-258° C.
Conditions: See reaction.notes.procedure_details.
Workup: This compound was prepared by a ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Monosulfide | Tertiary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | Other | null | null | null | CNC.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>>CN(C)c1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-32eed9b20fbe4a80a60b8ae09427c623 | CCN.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>>CCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=O)C.C(C)N>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCC)N(C1=O)C | [CH3:1][CH2:2][NH2:3].CS[c:4]1[n:5][cH:6][c:7]2[cH:8][c:9](-[c:10]3[c:11]([Cl:12])[cH:13][cH:14][cH:15][c:16]3[Cl:17])[c:18](=[O:19])[n:20]([CH3:21])[c:22]2[n:23]1>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][cH:6][c:7]2[cH:8][c:9](-[c:10]3[c:11]([Cl:12])[cH:13][cH:14][cH:15][c:16]3[Cl:17])[c:18](=[O:19])[n:20]([CH3:21])[c:22]2[n:... | CCN.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | CCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | df9d6a54bbeb74919f9913aad742e0b7c3ffefcaa8d2bb485e4914ba80c410ee | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=c1[nH]c2ncncc2cc1-c1ccccc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[c:4]:[c:5]:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[C;D1;H3:10]-[C:11]-[NH2;D1;+0:12]>>[C;D1;H3:10]-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[c:4]:[c:5]:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9] | null | [] | null | null | null | null | This compound was prepared by a procedure similar to that described in Example 40 starting with 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37 and ethylamine gas; mp 180°-182° C.
Conditions: See reaction.notes.procedure_details.
Workup: This compound was prepared by a pro... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | Other | null | null | null | CCN.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>>CCNc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d04022b22bcd4100a137a9c7f735c157 | CC(C)N.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>>CC(C)Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=O)C.C(C)(C)N>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC(C)C)N(C1=O)C | [CH3:1][CH:2]([CH3:3])[NH2:4].CS[c:5]1[n:6][cH:7][c:8]2[cH:9][c:10](-[c:11]3[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]3[Cl:18])[c:19](=[O:20])[n:21]([CH3:22])[c:23]2[n:24]1>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[n:6][cH:7][c:8]2[cH:9][c:10](-[c:11]3[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]3[Cl:18])[c:19](=[O:20])[n:21]([... | CC(C)N.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | CC(C)Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | df9d6a54bbeb74919f9913aad742e0b7c3ffefcaa8d2bb485e4914ba80c410ee | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=c1[nH]c2ncncc2cc1-c1ccccc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[c:4]:[c:5]:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[C;D1;H3:10]-[C:11](-[C;D1;H3:12])-[NH2;D1;+0:13]>>[C;D1;H3:10]-[C:11](-[C;D1;H3:12])-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[c:4]:[c:5]:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9] | null | [] | null | null | null | null | This compound was prepared by a procedure similar to that described in Example 40 starting with 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37 and isopropylamine; mp 194°-196° C.
Conditions: See reaction.notes.procedure_details.
Workup: This compound was prepared by a pro... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | Other | null | null | null | CC(C)N.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>>CC(C)Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a8f31c3f69e44f889459e4fbf80bb158 | CCCCN.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>>CCCCNN1C=c2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2=NC1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=O)C.C(CCC)N>>C(CCC)NN1CN=C2C(=C1)C=C(C(N2C)=O)C2=C(C=CC=C2Cl)Cl | [CH3:1][CH2:2][CH2:3][CH2:4][NH2:5].CS[c:25]1[n:6][cH:7][c:8]2[cH:9][c:10](-[c:11]3[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]3[Cl:18])[c:19](=[O:20])[n:21]([CH3:22])[c:23]2[n:24]1>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][N:6]1[CH:7]=[c:8]2[cH:9][c:10](-[c:11]3[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]3[Cl:18])[c:19](=[O:20]... | CCCCN.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | CCCCNN1C=c2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2=NC1 | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 43f5647777f5edceda750ecd7279b6936f64c6fee7f4496ecb94ddf45531c6e6 | 95c7086dc5e33844e8536f4de4a4643f8c4c6db67b746c1239865f1497b14f4e | O=c1[nH]c2c(cc1-c1ccccc1)=CNCN=2 | C-S-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3]2:[#7;a:4](-[C;D1;H3:5]):[c:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:2:[cH;D2;+0:10]:[n;H0;D2;+0:11]:1.[C:12]-[C:13]-[NH2;D1;+0:14]>>[C:12]-[C:13]-[NH;D2;+0:14]-[N;H0;D3;+0:11]1-[CH2;D2;+0:1]-[N;H0;D2;+0:2]=[c;H0;D3;+0:3]2:[#7;a:4](-[C;D1;H3:5]):[c:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:2=[... | null | [] | 110 | CELSIUS | 1 | HOUR | A mixture of 0.177 g (0.50 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37, 10 mL of n-butylamine and 1.0 mL of dimethylformamide was heated with stirring to reflux (110° C. oil bath). After 1 hour, solution was complete. After 20 hours reflux, the excess amine an... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Hydrazine | c1cnc2ncncc2c1 | C1=c2cccnc2=NC[NH]1 | C1=c2cccnc2=NC[NH]1.c1ccccc1 | Other | CN(C=O)C | 110 | 1 | CCCCN.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>CN(C=O)C>CCCCNN1C=c2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2=NC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-25e5f36c73a5443aa2d8d2b4bbb40382 | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.NCc1ccccc1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NCc3ccccc3)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=O)C.C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)C | CS[c:18]1[n:17][cH:16][c:15]2[cH:14][c:5](-[c:6]3[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]3[Cl:13])[c:3](=[O:4])[n:2]([CH3:1])[c:28]2[n:27]1.[NH2:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2[cH:16][n:17][c:18]... | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.NCc1ccccc1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NCc3ccccc3)nc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | df9d6a54bbeb74919f9913aad742e0b7c3ffefcaa8d2bb485e4914ba80c410ee | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=c1[nH]c2nc(NCc3ccccc3)ncc2cc1-c1ccccc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[NH2;D1;+0:10]-[C:11]-[c:12]>>[C;D1;H3:8]-[#7;a:7](:[c:9]):[c:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[C:11]-[c:12]):[#7;a:2]:[c:3]:[c:4]:1 | 47.6 | [{"value": 47.6, "product": "C(C1=CC=CC=C1)NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 5 | MINUTE | A mixture of 0.165 g (0.47 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido-[2,3-d]pyrimidin-7-one of Example 37, 0.50 g (4.70 mmol) of benzylamine and 0.5 mL of dimethylformamide was heated with stirring in a 120° C. oil bath. After 5 minutes, solution was complete. After 5 hours, the excess amine a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | Other | CN(C=O)C | 120 | 0.083333 | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.NCc1ccccc1>CN(C=O)C>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NCc3ccccc3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ed41f375aaff41018a80d7b0ecb415a0 | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.NCCCN1CCOCC1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NCCCN3CCOCC3)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=O)C.NCCCN1CCOCC1>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCOCC2)N(C1=O)C | CS[c:18]1[n:17][cH:16][c:15]2[cH:14][c:5](-[c:6]3[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]3[Cl:13])[c:3](=[O:4])[n:2]([CH3:1])[c:30]2[n:29]1.[NH2:19][CH2:20][CH2:21][CH2:22][N:23]1[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1>>[CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2... | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.NCCCN1CCOCC1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NCCCN3CCOCC3)nc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | df9d6a54bbeb74919f9913aad742e0b7c3ffefcaa8d2bb485e4914ba80c410ee | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=c1[nH]c2nc(NCCCN3CCOCC3)ncc2cc1-c1ccccc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9] | null | [] | 125 | CELSIUS | 2 | MINUTE | A mixture of 0.165 g (0.47 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37, 1.00 g (6.90 mmol) of N-(3-aminopropyl)morpholine and 0.5 mL of dimethylformamide was heated with stirring in a 125° C. oil bath. After 2 minutes, solution was complete. After 1.5 hours, t... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.C1COCC[NH]1 | Other | CN(C=O)C | 125 | 0.033333 | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.NCCCN1CCOCC1>CN(C=O)C>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NCCCN3CCOCC3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4065ebd450dd42b9b396a7e3dbade98c | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.NCc1ccccn1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NCc3ccccn3)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=O)C.NCC1=NC=CC=C1>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCC2=NC=CC=C2)N(C1=O)C | CS[c:18]1[n:17][cH:16][c:15]2[cH:14][c:5](-[c:6]3[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]3[Cl:13])[c:3](=[O:4])[n:2]([CH3:1])[c:28]2[n:27]1.[NH2:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][n:26]1>>[CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2[cH:16][n:17][c:18](... | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.NCc1ccccn1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NCc3ccccn3)nc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | df9d6a54bbeb74919f9913aad742e0b7c3ffefcaa8d2bb485e4914ba80c410ee | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=c1[nH]c2nc(NCc3ccccn3)ncc2cc1-c1ccccc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[#7;a:10]:[c:11]-[C:12]-[NH2;D1;+0:13]>>[#7;a:10]:[c:11]-[C:12]-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9] | 38.7 | [{"value": 38.7, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCC2=NC=CC=C2)N(C1=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 2 | MINUTE | A mixture of 0.165 g (0.47 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37, 1.08 g (10.0 mmol) of 2-(aminomethyl)pyridine and 0.5 mL of dimethylformamide was heated with stirring in a 130° C. oil bath. After 2 minutes, solution was complete. After 2 hours, the exc... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccncc1 | Other | CN(C=O)C | 130 | 0.033333 | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.NCc1ccccn1>CN(C=O)C>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NCc3ccccn3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f149ec04b04c43cd9da4e5fa56e0fec3 | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.NCc1cccnc1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NCc3cccnc3)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=O)C.NCC=1C=NC=CC1>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCC=2C=NC=CC2)N(C1=O)C | CS[c:18]1[n:17][cH:16][c:15]2[cH:14][c:5](-[c:6]3[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]3[Cl:13])[c:3](=[O:4])[n:2]([CH3:1])[c:28]2[n:27]1.[NH2:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][n:25][cH:26]1>>[CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2[cH:16][n:17][c:18](... | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.NCc1cccnc1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NCc3cccnc3)nc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | df9d6a54bbeb74919f9913aad742e0b7c3ffefcaa8d2bb485e4914ba80c410ee | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=c1[nH]c2nc(NCc3cccnc3)ncc2cc1-c1ccccc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[#7;a:10]:[c:11]:[c:12]-[C:13]-[NH2;D1;+0:14]>>[#7;a:10]:[c:11]:[c:12]-[C:13]-[NH;D2;+0:14]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9] | null | [] | null | null | null | null | This compound was prepared by a procedure similar to that described in Example 49 starting with 0.165 g (0.47 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37 and 1.08 g (10.0 mmol) of 3-(aminomethyl)-pyridine yielding 0.053 g of pure product; mp 224°-226° C.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccncc1 | Other | null | null | null | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.NCc1cccnc1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NCc3cccnc3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3a132906f38a4c07b3d4eb7a38743313 | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.NCCc1ccccn1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NCCc3ccccn3)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=O)C.NCCC1=NC=CC=C1>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCC2=NC=CC=C2)N(C1=O)C | CS[c:18]1[n:17][cH:16][c:15]2[cH:14][c:5](-[c:6]3[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]3[Cl:13])[c:3](=[O:4])[n:2]([CH3:1])[c:29]2[n:28]1.[NH2:19][CH2:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][n:27]1>>[CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2[cH:16][n:17... | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.NCCc1ccccn1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NCCc3ccccn3)nc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | df9d6a54bbeb74919f9913aad742e0b7c3ffefcaa8d2bb485e4914ba80c410ee | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=c1[nH]c2nc(NCCc3ccccn3)ncc2cc1-c1ccccc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9] | null | [] | null | null | null | null | This compound was prepared by a procedure similar to that described in Example 49 starting with 0.165 g (0.47 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37 and 1.00 g (8.20 mmol) of 2-(2-aminoethyl)-pyridine yielding 0.082 g of pure product; mp 173°-174° C.
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccncc1 | Other | null | null | null | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.NCCc1ccccn1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NCCc3ccccn3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-16b1b5b57c634a8aa4a0c762c66831e2 | COc1ccccc1N1CCN(CCCN)CC1.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>>COc1ccccc1N1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)CC1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=O)C.NCCCN1CCN(CC1)C1=C(C=CC=C1)OC>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCN2CCN(CC2)C2=C(C=CC=C2)OC)N(C1=O)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([CH2:13][CH2:14][CH2:15][NH2:16])[CH2:37][CH2:38]1.CS[c:17]1[n:18][cH:19][c:20]2[cH:21][c:22](-[c:23]3[c:24]([Cl:25])[cH:26][cH:27][cH:28][c:29]3[Cl:30])[c:31](=[O:32])[n:33]([CH3:34])[c:35]2[n:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][... | COc1ccccc1N1CCN(CCCN)CC1.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | COc1ccccc1N1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | df9d6a54bbeb74919f9913aad742e0b7c3ffefcaa8d2bb485e4914ba80c410ee | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=c1[nH]c2nc(NCCCN3CCN(c4ccccc4)CC3)ncc2cc1-c1ccccc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9] | null | [] | null | null | null | null | This compound was prepared by a procedure similar to that described in Example 49 starting with 0.165 g (0.47 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37 and 1.00 g (4.00 mmol) of 1-(3-aminopropyl)-4-(2-methoxyphenyl)piperazine yielding 0.103 g of pure product... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.C1C[NH]CC[NH]1.c1cnc2ncncc2c1.c1ccccc1 | Other | null | null | null | COc1ccccc1N1CCN(CCCN)CC1.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>>COc1ccccc1N1CCN(CCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0aaab490559345e3a5659881e04302db | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.Nc1ccccc1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccccc3)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)C.NC1=CC=CC=C1>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC=CC=C2)N(C1=O)C | CS(=O)(=O)[c:18]1[n:17][cH:16][c:15]2[cH:14][c:5](-[c:6]3[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]3[Cl:13])[c:3](=[O:4])[n:2]([CH3:1])[c:27]2[n:26]1.[NH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2[cH:16][n:17][c:18]... | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.Nc1ccccc1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccccc3)nc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:8]-[#7;a:7](:[c:9]):[c:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:[c:4]:1 | null | [] | 184 | CELSIUS | null | null | A solution of 0.113 g (0.29 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 in 1.00 g (10.70 mmol) of aniline was maintained at reflux (184° C.) for 3 minutes. Most of the excess aniline was evaporated at reduced pressure. The remaining gum was dissolved in 1.0 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | null | 184 | null | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.Nc1ccccc1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccccc3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2fa6392e84c549aa85701a13e6abad4d | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.Nc1ccc(Cl)cc1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc(Cl)cc3)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)C.ClC1=CC=C(N)C=C1>>ClC1=CC=C(C=C1)NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)C | CS(=O)(=O)[c:18]1[n:17][cH:16][c:15]2[cH:14][c:5](-[c:6]3[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]3[Cl:13])[c:3](=[O:4])[n:2]([CH3:1])[c:28]2[n:27]1.[NH2:19][c:20]1[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]1>>[CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2[cH:16][n:1... | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.Nc1ccc(Cl)cc1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc(Cl)cc3)nc21 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:8]-[#7;a:7](:[c:9]):[c:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:[c:4]:1 | null | [] | 238 | CELSIUS | 5 | MINUTE | A mixture of 0.113 g (0.29 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 in 0.50 g (3.90 mmol) of 4-chloroaniline was heated, with stirring, at the boiling point (238° C.) for 5 minutes. Ethyl acetate (3 mL) was added to the cooled dark blue reaction solution. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | C(C)(=O)OCC | 238 | 0.083333 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.Nc1ccc(Cl)cc1>C(C)(=O)OCC>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc(Cl)cc3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-229e6ead42474df5b581ec87f76dc9f1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.Nc1ccc2c(c1)OCO2>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc4c(c3)OCO4)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)C.C1OC=2C=C(N)C=CC2O1>>O1COC2=C1C=CC(=C2)NC=2N=CC1=C(N2)N(C(C(=C1)C1=C(C=CC=C1Cl)Cl)=O)C | CS(=O)(=O)[c:18]1[n:17][cH:16][c:15]2[cH:14][c:5](-[c:6]3[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]3[Cl:13])[c:3](=[O:4])[n:2]([CH3:1])[c:30]2[n:29]1.[NH2:19][c:20]1[cH:21][cH:22][c:23]2[c:24]([cH:25]1)[O:26][CH2:27][O:28]2>>[CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:1... | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.Nc1ccc2c(c1)OCO2 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc4c(c3)OCO4)nc21 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(Nc3ccc4c(c3)OCO4)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:8]-[#7;a:7](:[c:9]):[c:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:[c:4]:1 | null | [] | 200 | CELSIUS | null | null | A mixture of 0.113 g (0.29 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.50 g (3.70 mmol) of 3,4-methylenedioxyaniline was heated, with stirring, in a 200° C. oil bath. The resulting solution was heated for 5 minutes and cooled to room temperature. Ethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccc2c(c1)OCO2 | HO- | C(C)(=O)OCC | 200 | null | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.Nc1ccc2c(c1)OCO2>C(C)(=O)OCC>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc4c(c3)OCO4)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-93c51878ae8a413eb4db15ce380f4843 | CN1CCN(CCCCN)CC1.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>>CN1CCN(CCCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)CC1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=O)C.NCCCCN1CCN(CC1)C>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCCN2CCN(CC2)C)N(C1=O)C | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH2:9][NH2:10])[CH2:31][CH2:32]1.CS[c:11]1[n:12][cH:13][c:14]2[cH:15][c:16](-[c:17]3[c:18]([Cl:19])[cH:20][cH:21][cH:22][c:23]3[Cl:24])[c:25](=[O:26])[n:27]([CH3:28])[c:29]2[n:30]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][c:11]2[n:12][c... | CN1CCN(CCCCN)CC1.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | CN1CCN(CCCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)CC1 | null | null | CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | df9d6a54bbeb74919f9913aad742e0b7c3ffefcaa8d2bb485e4914ba80c410ee | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=c1[nH]c2nc(NCCCCN3CCNCC3)ncc2cc1-c1ccccc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9] | null | [] | 170 | CELSIUS | 2 | MINUTE | A mixture of 0.152 g (0.43 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8-pyrido[2,3-d]pyrimidin-7-one of Example 37 and 0.50 g (2.90 mmol) of 1-(4-aminobutyl)-4-methylpiperazine was heated with stirring in a 170° C. oil bath. After 2 minutes, solution was complete. After 2 hours, the solution was cooled t... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | C1C[NH]CC[NH]1.c1cnc2ncncc2c1.c1ccccc1 | Other | CCOCC | 170 | 0.033333 | CN1CCN(CCCCN)CC1.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>CCOCC>CN1CCN(CCCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3191b5ba687c4a38ba69160188ee969d | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.NC1CCCCC1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NC3CCCCC3)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)C.C1(CCCCC1)N>>C1(CCCCC1)NC=1N=CC2=C(N1)N(C(C(=C2)C2=C(C=CC=C2Cl)Cl)=O)C | CS(=O)(=O)[c:18]1[n:17][cH:16][c:15]2[cH:14][c:5](-[c:6]3[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]3[Cl:13])[c:3](=[O:4])[n:2]([CH3:1])[c:27]2[n:26]1.[NH2:19][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1>>[CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2[cH:16][n:17]... | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.NC1CCCCC1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NC3CCCCC3)nc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(NC3CCCCC3)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13]>>[C:10]-[C:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9])-[C:13] | null | [] | 134 | CELSIUS | null | null | A mixture of 0.100 g (0.26 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.300 g (3.00 mmol) of cyclohexylamine was heated to the boiling point (134° C.). The resulting solution was heated at reflux for 2 minutes. Most of the excess amine was evaporated at ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.C1CCCCC1 | HO- | null | 134 | null | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.NC1CCCCC1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(NC3CCCCC3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7c0d2f4521364c5dbc8d4b38d2935639 | Cc1ccc(N)cc1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>>Cc1ccc(NN2C=c3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3=NC2)cc1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)C.CC1=CC=C(N)C=C1>>ClC1=C(C(=CC=C1)Cl)C1=CC=2C(=NCN(C2)NC2=CC=C(C=C2)C)N(C1=O)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:27][cH:28]1.CS(=O)(=O)[c:26]1[n:7][cH:8][c:9]2[cH:10][c:11](-[c:12]3[c:13]([Cl:14])[cH:15][cH:16][cH:17][c:18]3[Cl:19])[c:20](=[O:21])[n:22]([CH3:23])[c:24]2[n:25]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][N:7]2[CH:8]=[c:9]3[cH:10][c:11](-[c:12]4[c:13]([Cl:14])[cH:15][cH:16][cH:... | Cc1ccc(N)cc1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21 | Cc1ccc(NN2C=c3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3=NC2)cc1 | null | null | null | Miscellaneous | OtherReaction | 2261235475fc28ea339785b3b09ba6fac4ff17f1ffda032b5b9b36e8c4844217 | 01029f5a8ad6bf4b4408b4ba553d43977ce413937313c5e69fb72996996c7328 | O=c1[nH]c2c(cc1-c1ccccc1)=CN(Nc1ccccc1)CN=2 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3]2:[#7;a:4](-[C;D1;H3:5]):[c:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]:2:[cH;D2;+0:10]:[n;H0;D2;+0:11]:1.[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[C;D1;H3:5]-[#7;a:4]1:[c:6]:[c:7]:[c:8]:[c;H0;D3;+0:9]2:[c;H0;D3;+0:3]:1=[N;H0;D2;+0:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:11](-[NH;D2;+0:12]... | null | [] | 180 | CELSIUS | null | null | A mixture of 0.113 g (0.29 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.50 g (4.70 mmol) of 4-methylaniline was heated, with stirring, in a 180° C. oil bath. The resulting solution was heated for 10 minutes. Much of the excess 4-methylaniline was evapora... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Hydrazine | c1cnc2ncncc2c1 | C1=c2cccnc2=NC[NH]1 | c1ccccc1.C1=c2cccnc2=NC[NH]1.c1ccccc1 | HO- | null | 180 | null | Cc1ccc(N)cc1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>>Cc1ccc(NN2C=c3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3=NC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2385e0240fd44243a34f8caa93efa84f | COc1ccc(N)cc1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>>COc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)C.COC1=CC=C(N)C=C1>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC=C(C=C2)OC)N(C1=O)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:28][cH:29]1.CS(=O)(=O)[c:8]1[n:9][cH:10][c:11]2[cH:12][c:13](-[c:14]3[c:15]([Cl:16])[cH:17][cH:18][cH:19][c:20]3[Cl:21])[c:22](=[O:23])[n:24]([CH3:25])[c:26]2[n:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]3[cH:12][c:13](-[c:14]4[c:15]([Cl:16])[... | COc1ccc(N)cc1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21 | COc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[c:4]:[c:5]:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:8]-[#7;a:7](:[c:9]):[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:6]:[c:5]:[c:4]:1 | null | [] | 180 | CELSIUS | null | null | A mixture of 0.113 g (0.29 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.50 g (4.10 mmol) of 4-methoxyaniline was heated, with stirring, in a 180° C. oil bath. The resulting solution was heated for 10 minutes. Much of the excess aniline was evaporated at ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | null | 180 | null | COc1ccc(N)cc1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>>COc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8675cbe68b9f48d288dee7a6e5c59cad | CC(=O)OC(C)=O.CCn1c(=N)c(-c2c(Cl)cccc2Cl)cc2cnc(SC)nc21>>CCn1c(=NC(C)=O)c(-c2c(Cl)cccc2Cl)cc2cnc(SC)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=N)CC.C(C)(=O)OC(C)=O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=NC(C)=O)CC | CC(=O)O[C:6]([CH3:7])=[O:8].[CH3:1][CH2:2][n:3]1[c:4](=[NH:5])[c:9](-[c:10]2[c:11]([Cl:12])[cH:13][cH:14][cH:15][c:16]2[Cl:17])[cH:18][c:19]2[cH:20][n:21][c:22]([S:23][CH3:24])[n:25][c:26]12>>[CH3:1][CH2:2][n:3]1[c:4](=[N:5][C:6]([CH3:7])=[O:8])[c:9](-[c:10]2[c:11]([Cl:12])[cH:13][cH:14][cH:15][c:16]2[Cl:17])[cH:18][c:... | CC(=O)OC(C)=O.CCn1c(=N)c(-c2c(Cl)cccc2Cl)cc2cnc(SC)nc21 | CCn1c(=NC(C)=O)c(-c2c(Cl)cccc2Cl)cc2cnc(SC)nc21 | null | null | null | Acylation | Aminolysis of esters | 868ba94f028b30e9347f1568001d166d126ab48ad34862bd252bb72f87967edd | 93289da630dbaf2d9339c4212dcd342dfbcc29df4e79a63418a0fd9f589abdc1 | N=c1[nH]c2ncncc2cc1-c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]:[c:5]:[#7;a:6](-[C:7]):[c:8](=[NH;D1;+0:9]):[c:10]>>[#7;a:4]:[c:5]:[#7;a:6](-[C:7]):[c:8](=[N;H0;D2;+0:9]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:10] | null | [] | null | null | null | null | A mixture of 2.70 g (7.40 mmol) of 6-(2,6-dichlorophenyl)-8-ethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-ylideneamine of Example 65 and 15 mL of acetic anhydride was heated with stirring to the boiling point. The resulting solution was heated at reflux for 5 minutes and concentrated at reduced pressure to ca. 8 m... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | null | null | null | c1ccccc1.c1cnc2ncncc2c1 | HO- | null | null | null | CC(=O)OC(C)=O.CCn1c(=N)c(-c2c(Cl)cccc2Cl)cc2cnc(SC)nc21>>CCn1c(=NC(C)=O)c(-c2c(Cl)cccc2Cl)cc2cnc(SC)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4ca4e30594e44f88b0f99fc7322a410a | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.Nc1ccccc1>>CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccccc3)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)CC.NC1=CC=CC=C1>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC=CC=C2)N(C1=O)CC | CS(=O)(=O)[c:19]1[n:18][cH:17][c:16]2[cH:15][c:6](-[c:7]3[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]3[Cl:14])[c:4](=[O:5])[n:3]([CH2:2][CH3:1])[c:28]2[n:27]1.[NH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6](-[c:7]2[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]2[Cl:14])[cH:15][c:16]2[cH... | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.Nc1ccccc1 | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccccc3)nc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:8]-[#7;a:7](:[c:9]):[c:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:[c:4]:1 | null | [] | 195 | CELSIUS | null | null | A mixture of 0.134 g (0.33 mmol) of 6-(2,6-dichlorophenyl)-8-ethyl-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 68 and 0.500 g (5.40 mmol) of aniline was heated with stirring in a 195° C. oil bath to reflux. The resulting solution was maintained at reflux for 5 minutes. Most of the excess aniline was ev... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | null | 195 | null | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.Nc1ccccc1>>CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccccc3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2a5b023190f34924a6abcd11c41e178a | COc1ccccc1N.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>>COc1ccccc1Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)C.COC1=C(N)C=CC=C1>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=C(C=CC=C2)OC)N(C1=O)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH2:9].CS(=O)(=O)[c:10]1[n:11][cH:12][c:13]2[cH:14][c:15](-[c:16]3[c:17]([Cl:18])[cH:19][cH:20][cH:21][c:22]3[Cl:23])[c:24](=[O:25])[n:26]([CH3:27])[c:28]2[n:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[NH:9][c:10]1[n:11][cH:12][c:13]2[cH:14][c:15](-[c:16]3[c:1... | COc1ccccc1N.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21 | COc1ccccc1Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | null | null | CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:8]-[#7;a:7](:[c:9]):[c:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:[c:4]:1 | null | [] | 175 | CELSIUS | null | null | A mixture of 0.113 g (0.29 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.50 g (4.10 mmol) of 2-methoxyaniline was heated, with stirring, in a 175° C. oil bath. The resulting solution was heated for 5 minutes and cooled to room temperature. Ether (2 mL) wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | CCOCC | 175 | null | COc1ccccc1N.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>CCOCC>COc1ccccc1Nc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-eda16d28ddde4d29b868c0f9438c5f73 | COc1ccc(N)cc1C.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>>COc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1C | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)C.CC=1C=C(N)C=CC1OC>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC(=C(C=C2)OC)C)N(C1=O)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:28][c:29]1[CH3:30].CS(=O)(=O)[c:8]1[n:9][cH:10][c:11]2[cH:12][c:13](-[c:14]3[c:15]([Cl:16])[cH:17][cH:18][cH:19][c:20]3[Cl:21])[c:22](=[O:23])[n:24]([CH3:25])[c:26]2[n:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]3[cH:12][c:13](-[c:14]4[c:15]([C... | COc1ccc(N)cc1C.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21 | COc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1C | null | null | CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[c:4]:[c:5]:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:8]-[#7;a:7](:[c:9]):[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:6]:[c:5]:[c:4]:1 | null | [] | 165 | CELSIUS | null | null | A mixture of 0.113 g (0.29 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.40 g (2.90 mmol) of 3-methyl-4-methoxyaniline was heated, with stirring, in a 165° C. oil bath. The resulting solution was heated for 5 minutes and cooled to room temperature. Ether ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | CCOCC | 165 | null | COc1ccc(N)cc1C.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>CCOCC>COc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-68d8ae5623a045faa4752c54188d8074 | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.COc1ccc(N)cc1>>CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc(OC)cc3)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)CC.COC1=CC=C(N)C=C1>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC=C(C=C2)OC)N(C1=O)CC | CS(=O)(=O)[c:19]1[n:18][cH:17][c:16]2[cH:15][c:6](-[c:7]3[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]3[Cl:14])[c:4](=[O:5])[n:3]([CH2:2][CH3:1])[c:30]2[n:29]1.[NH2:20][c:21]1[cH:22][cH:23][c:24]([O:25][CH3:26])[cH:27][cH:28]1>>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6](-[c:7]2[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]2[Cl:14])[c... | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.COc1ccc(N)cc1 | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc(OC)cc3)nc21 | null | O | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:8]-[#7;a:7](:[c:9]):[c:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:[c:4]:1 | null | [] | null | null | null | null | A solution of 0.100 g (0.25 mmol) of 6-(2,6-dichlorophenyl)-8-ethyl-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 68 and 0.061 g (0.50 mmol) of 4-methoxyaniline in 0.5 mL of dimethylformamide was heated at reflux for 10 minutes. Three drops of water were added. Crystals separated on inducement. An additi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | O.CN(C=O)C | null | null | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.COc1ccc(N)cc1>O.CN(C=O)C>CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc(OC)cc3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e03019db057645d990f6974409cc35bc | CCOc1ccc(N)cc1.CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>>CCOc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(CC)c3n2)cc1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)CC.C(C)OC1=CC=C(N)C=C1>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC=C(C=C2)OCC)N(C1=O)CC | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:30][cH:31]1.CS(=O)(=O)[c:9]1[n:10][cH:11][c:12]2[cH:13][c:14](-[c:15]3[c:16]([Cl:17])[cH:18][cH:19][cH:20][c:21]3[Cl:22])[c:23](=[O:24])[n:25]([CH2:26][CH3:27])[c:28]2[n:29]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][c:12]3[cH:13][c:14](... | CCOc1ccc(N)cc1.CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21 | CCOc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(CC)c3n2)cc1 | null | null | C(C)(=O)O.O | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:8]-[#7;a:7](:[c:9]):[c:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:[c:4]:1 | null | [] | null | null | null | null | A mixture of 0.150 g (0.38 mmol) of 6-(2,6-dichlorophenyl)-8-ethyl-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 68 and 0.500 g (3.60 mmol) of 4-ethoxyaniline was fused in a 160° C. oil bath for 10 minutes. The dark violet melt was cooled and dissolved in 1 mL of warm glacial acetic acid. This solution w... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | C(C)(=O)O.O | null | null | CCOc1ccc(N)cc1.CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>C(C)(=O)O.O>CCOc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(CC)c3n2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-81f4c40125694e76a49bac3d81b5f484 | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.COc1ccc(N)cc1OC>>CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc(OC)c(OC)c3)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)CC.COC=1C=C(N)C=CC1OC>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC(=C(C=C2)OC)OC)N(C1=O)CC | CS(=O)(=O)[c:19]1[n:18][cH:17][c:16]2[cH:15][c:6](-[c:7]3[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]3[Cl:14])[c:4](=[O:5])[n:3]([CH2:2][CH3:1])[c:32]2[n:31]1.[NH2:20][c:21]1[cH:22][cH:23][c:24]([O:25][CH3:26])[c:27]([O:28][CH3:29])[cH:30]1>>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6](-[c:7]2[c:8]([Cl:9])[cH:10][cH:11][cH:12][c... | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.COc1ccc(N)cc1OC | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc(OC)c(OC)c3)nc21 | null | null | C(C)(=O)O.O | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:8]-[#7;a:7](:[c:9]):[c:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:[c:4]:1 | null | [] | 160 | CELSIUS | null | null | A mixture of 0.150 g (0.38 mmol) of 6-(2,6-dichlorophenyl)-8-ethyl-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 68 and 0.500 g (3.30 mmol) of 3,4-dimethoxyaniline was heated in a 160° C. oil bath for 5 minutes. The dark blue solution was cooled and dissolved in 2 mL of warm glacial acetic acid. This sol... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | C(C)(=O)O.O | 160 | null | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.COc1ccc(N)cc1OC>C(C)(=O)O.O>CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3ccc(OC)c(OC)c3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-76f6a432b29140da8181c2f2c78550f6 | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.COc1cc(N)cc(OC)c1OC>>CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3cc(OC)c(OC)c(OC)c3)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)CC.COC=1C=C(N)C=C(C1OC)OC>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC(=C(C(=C2)OC)OC)OC)N(C1=O)CC | CS(=O)(=O)[c:19]1[n:18][cH:17][c:16]2[cH:15][c:6](-[c:7]3[c:8]([Cl:9])[cH:10][cH:11][cH:12][c:13]3[Cl:14])[c:4](=[O:5])[n:3]([CH2:2][CH3:1])[c:34]2[n:33]1.[NH2:20][c:21]1[cH:22][c:23]([O:24][CH3:25])[c:26]([O:27][CH3:28])[c:29]([O:30][CH3:31])[cH:32]1>>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[c:6](-[c:7]2[c:8]([Cl:9])[cH:10][... | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.COc1cc(N)cc(OC)c1OC | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3cc(OC)c(OC)c(OC)c3)nc21 | null | null | C(C)(=O)O.O | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C:8]-[#7;a:7](:[c:9]):[c:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:[c:4]:1 | null | [] | 160 | CELSIUS | null | null | A mixture of 0.150 g (0.38 mmol) of 6-(2,6-dichlorophenyl)-8-ethyl-2-methanesulfonyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 68 and 0.500 g (2.70 mmol) of 3,4,5-trimethoxyaniline was heated in a 160° C. oil bath for 5 minutes. The dark solution was cooled and dissolved in 2 mL of warm glacial acetic acid. This solut... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | C(C)(=O)O.O | 160 | null | CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.COc1cc(N)cc(OC)c1OC>C(C)(=O)O.O>CCn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3cc(OC)c(OC)c(OC)c3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e995bd2a805644e4b3e1fc791d696150 | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.Nc1cccnc1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3cccnc3)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=O)C.NC=1C=NC=CC1.Cl.NC=1C=NC=CC1>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC=2C=NC=CC2)N(C1=O)C | CS[c:18]1[n:17][cH:16][c:15]2[cH:14][c:5](-[c:6]3[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]3[Cl:13])[c:3](=[O:4])[n:2]([CH3:1])[c:27]2[n:26]1.[NH2:19][c:20]1[cH:21][cH:22][cH:23][n:24][cH:25]1>>[CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2[cH:16][n:17][c:18]([NH:19][... | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.Nc1cccnc1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3cccnc3)nc21 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | df9d6a54bbeb74919f9913aad742e0b7c3ffefcaa8d2bb485e4914ba80c410ee | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=c1[nH]c2nc(Nc3cccnc3)ncc2cc1-c1ccccc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]:[#7;a:14]:[c:15]>>[C;D1;H3:8]-[#7;a:7](:[c:9]):[c:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]:[#7;a:14]:[c:15]):[#7;a:2]:[c:3]:[c:4]:1 | null | [] | 210 | CELSIUS | 1 | HOUR | A mixture of 0.165 g (0.47 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37, 0.500 g (5.30 mmol) of 3-aminopyridine base, and 0.066 g (0.50 mmol) of 3-aminopyridine hydrochloride was heated with stirring in a 210° C. oil bath for 1 hour. Water (5 mL) was added to t... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccncc1 | Other | O | 210 | 1 | CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1.Nc1cccnc1>O>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3cccnc3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0ccd6005f4ca42f39fa580909f4210c7 | CCN(CC)CCOc1ccc(N)cc1.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>>CCN(CC)CCOc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=O)C.C(C)N(CCOC1=CC=C(N)C=C1)CC.COCCOCCOC>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC=C(C=C2)OCCN(CC)CC)N(C1=O)C | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:34][cH:35]1.CS[c:14]1[n:15][cH:16][c:17]2[cH:18][c:19](-[c:20]3[c:21]([Cl:22])[cH:23][cH:24][cH:25][c:26]3[Cl:27])[c:28](=[O:29])[n:30]([CH3:31])[c:32]2[n:33]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:1... | CCN(CC)CCOc1ccc(N)cc1.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | CCN(CC)CCOc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | df9d6a54bbeb74919f9913aad742e0b7c3ffefcaa8d2bb485e4914ba80c410ee | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:8]-[#7;a:7](:[c:9]):[c:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:[c:4]:1 | null | [] | 150 | CELSIUS | null | null | A mixture of 0.155 g (0.40 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37, 0.167 g (0.80 mmol) of 4-(2-diethylaminoethoxy)aniline and 1 mL of (2-methoxyethyl)ether (bp 162° C.) was heated with stirring in a 150° C. oil bath. All solid gradually dissolved over a p... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | Other | O | 150 | null | CCN(CC)CCOc1ccc(N)cc1.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>O>CCN(CC)CCOc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-792d4796913a47ddb4ef1bb450d8932d | CN1CCN(CCCCCN)CC1.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>>CN1CCN(CCCCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)CC1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)SC)N(C1=O)C.NCCCCCN1CCN(CC1)C>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NCCCCCN2CCN(CC2)C)N(C1=O)C | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH2:11])[CH2:32][CH2:33]1.CS[c:12]1[n:13][cH:14][c:15]2[cH:16][c:17](-[c:18]3[c:19]([Cl:20])[cH:21][cH:22][cH:23][c:24]3[Cl:25])[c:26](=[O:27])[n:28]([CH3:29])[c:30]2[n:31]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11... | CN1CCN(CCCCCN)CC1.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1 | CN1CCN(CCCCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)CC1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | df9d6a54bbeb74919f9913aad742e0b7c3ffefcaa8d2bb485e4914ba80c410ee | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=c1[nH]c2nc(NCCCCCN3CCNCC3)ncc2cc1-c1ccccc1 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9] | null | [] | null | null | 2 | MINUTE | A mixture of 0.165 g (0.47 mmol) of 6-(2,6-dichlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 37 and 0.50 g (2.70 mmol) of 1-(5-aminopentyl)-4-methylpiperazine was heated with stirring in a 180° C. to 185° C. oil bath. After 2 minutes, solution was complete. After 0.5 hour, the solutio... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | C1C[NH]CC[NH]1.c1cnc2ncncc2c1.c1ccccc1 | Other | O | null | 0.033333 | CN1CCN(CCCCCN)CC1.CSc1ncc2cc(-c3c(Cl)cccc3Cl)c(=O)n(C)c2n1>O>CN1CCN(CCCCCNc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4b3709d670944052a53ca165365f8b96 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.Nc1cccc(CO)c1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3cccc(CO)c3)nc21 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)C.OCC=1C=C(N)C=CC1.C(C)(=O)O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC(=CC=C2)CO)N(C1=O)C | CS(=O)(=O)[c:18]1[n:17][cH:16][c:15]2[cH:14][c:5](-[c:6]3[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]3[Cl:13])[c:3](=[O:4])[n:2]([CH3:1])[c:29]2[n:28]1.[NH2:19][c:20]1[cH:21][cH:22][cH:23][c:24]([CH2:25][OH:26])[cH:27]1>>[CH3:1][n:2]1[c:3](=[O:4])[c:5](-[c:6]2[c:7]([Cl:8])[cH:9][cH:10][cH:11][c:12]2[Cl:13])[cH:14][c:15]2[cH... | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.Nc1cccc(CO)c1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3cccc(CO)c3)nc21 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:8]-[#7;a:7](:[c:9]):[c:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:[c:4]:1 | null | [] | 180 | CELSIUS | null | null | A mixture of 0.155 g (0.40 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.500 g (4.10 mmol) of 3-(hydroxymethyl)aniline was heated in a 180° C. oil bath for 10 minutes. At ca. 120° C., 2 mL of glacial acetic acid were added to dissolve the gum. Water (20 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | O | 180 | null | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21.Nc1cccc(CO)c1>O>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(Nc3cccc(CO)c3)nc21 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8f36c1ceeca8456d85e3fbff6f422fe7 | COc1cc(N)cc(OC)c1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>>COc1cc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc(OC)c1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)C.COC=1C=C(N)C=C(C1)OC.C(C)(=O)O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC(=CC(=C2)OC)OC)N(C1=O)C | [CH3:1][O:2][c:3]1[cH:4][c:5]([NH2:6])[cH:27][c:28]([O:29][CH3:30])[cH:31]1.CS(=O)(=O)[c:7]1[n:8][cH:9][c:10]2[cH:11][c:12](-[c:13]3[c:14]([Cl:15])[cH:16][cH:17][cH:18][c:19]3[Cl:20])[c:21](=[O:22])[n:23]([CH3:24])[c:25]2[n:26]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([NH:6][c:7]2[n:8][cH:9][c:10]3[cH:11][c:12](-[c:13]4[c:14]([... | COc1cc(N)cc(OC)c1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21 | COc1cc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc(OC)c1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[c:4]:[c:5]:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:8]-[#7;a:7](:[c:9]):[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:6]:[c:5]:[c:4]:1 | null | [] | 160 | CELSIUS | null | null | A mixture of 0.155 g (0.40 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.400 g (2.60 mmol) of 3,5-dimethoxyaniline was heated in a 160° C. oil bath for 5 minutes. At ca. 100° C., 1 mL of glacial acetic acid was added to the melt to dissolve. Water (10 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | O | 160 | null | COc1cc(N)cc(OC)c1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>O>COc1cc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc(OC)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4568d01a95fc402ebb6310c7c420554f | COC(=O)Cc1ccc(N)cc1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>>COC(=O)Cc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)C.NC1=CC=C(C=C1)CC(=O)OC.C(C)(=O)O>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC2=CC=C(C=C2)CC(=O)OC)N(C1=O)C | [CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:31][cH:32]1.CS(=O)(=O)[c:11]1[n:12][cH:13][c:14]2[cH:15][c:16](-[c:17]3[c:18]([Cl:19])[cH:20][cH:21][cH:22][c:23]3[Cl:24])[c:25](=[O:26])[n:27]([CH3:28])[c:29]2[n:30]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([NH:10][c:11]2[n:12][cH:13... | COC(=O)Cc1ccc(N)cc1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21 | COC(=O)Cc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(Nc3ccccc3)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:8]-[#7;a:7](:[c:9]):[c:5]1:[#7;a:6]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[#7;a:2]:[c:3]:[c:4]:1 | null | [] | null | null | null | null | A mixture of 0.226 g (0.58 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.40 g (2.80 mmol) of 4-aminophenylacetic acid, methyl ester base was heated in a 160° C. to 165° C. oil bath. The resulting solution was heated for 10 minutes and cooled to room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccccc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | O | null | null | COC(=O)Cc1ccc(N)cc1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>O>COC(=O)Cc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-09f50aa656964facbcc08ceb73b76632 | COc1ccc(N)cn1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>>COc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cn1 | ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)S(=O)(=O)C)N(C1=O)C.NC=1C=CC(=NC1)OC>>ClC1=C(C(=CC=C1)Cl)C1=CC2=C(N=C(N=C2)NC=2C=NC(=CC2)OC)N(C1=O)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:28][n:29]1.CS(=O)(=O)[c:8]1[n:9][cH:10][c:11]2[cH:12][c:13](-[c:14]3[c:15]([Cl:16])[cH:17][cH:18][cH:19][c:20]3[Cl:21])[c:22](=[O:23])[n:24]([CH3:25])[c:26]2[n:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]3[cH:12][c:13](-[c:14]4[c:15]([Cl:16])[c... | COc1ccc(N)cn1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21 | COc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cn1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 4829c7fa353840c036de48b4c116a7d68d2d5d8395d0f64d6e8c63d9a9bd4025 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | O=c1[nH]c2nc(Nc3cccnc3)ncc2cc1-c1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[c:4]:[c:5]:[#7;a:6]:1):[#7;a:7](-[C;D1;H3:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]:[#7;a:14]:[c:15]>>[C;D1;H3:8]-[#7;a:7](:[c:9]):[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]:[#7;a:14]:[c:15]):[#7;a:6]:[c:5]:[c:4]:1 | null | [] | 160 | CELSIUS | null | null | A mixture of 0.155 g (0.40 mmol) of 6-(2,6-dichlorophenyl)-2-methanesulfonyl-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one of Example 39 and 0.50 g (4.00 mmol) of 5-amino-2-methoxypyridine was heated, with stirring, in a 160° C. oil bath. The resulting solution was heated for 10 minutes and cooled to room temperature. Water... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1ccncc1.c1cnc2ncncc2c1.c1ccccc1 | HO- | O | 160 | null | COc1ccc(N)cn1.Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2cnc(S(C)(=O)=O)nc21>O>COc1ccc(Nc2ncc3cc(-c4c(Cl)cccc4Cl)c(=O)n(C)c3n2)cn1 |
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