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-0387783899c642a8b7eb4ba379bcdf5d | ord-f1d1a30eab97407f8e26262ae5a1d46f | CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.O=C(Cl)c1cc(F)ccc1F>>CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)c3cc(F)ccc3F)cc2s1 | NCCC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.C(C)N(CC)CC.FC1=C(C(=O)Cl)C=C(C=C1)F>>C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)C(CCNC(C2=C(C=CC(=C2)F)F)=O)=O | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][CH2:16][NH2:17])[cH:28][c:29]2[s:30]1.Cl[C:18](=[O:19])[c:20]1[cH:21][c:22]([F:23])[cH:24][cH:25][c:26]1[F:27]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][CH2:16... | CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.O=C(Cl)c1cc(F)ccc1F | CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)c3cc(F)ccc3F)cc2s1 | null | null | CN(C)C=O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(CCNC(=O)c1ccccc1)c1ccc2ncsc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[C:7]-[C:8]-[C:9]=[O;D1;H0:10]>>[O;D1;H0:10]=[C:9]-[C:8]-[C:7]-[NH;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 22 | [{"value": 22.0, "product": "C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)C(CCNC(C2=C(C=CC(=C2)F)F)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Similar to the synthesis of Example 249, a mixture of 1-(6-(3-aminopropanoyl)-2-benzothiazolyl)-3-ethylurea, triethylamine and 2,5-difluorobenzoyl chloride in DMF was reacted to give the desired compound 0.019 g (22%). LC/MS 433.0 (M+1); LC retention time 2.94 min.
Conditions: See reaction.notes.procedure_details.
Work... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2scnc2c1.c1ccccc1 | HCl | CN(C)C=O | null | null | CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.O=C(Cl)c1cc(F)ccc1F>CN(C)C=O>CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)c3cc(F)ccc3F)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a17e519171264a8d8ae9d98f193b2ac4 | C=O.CCNC(=O)Nc1nc2ccc(Br)cc2s1.CN>>CCN1CN(C)CN(c2nc3ccc(Br)cc3s2)C1=O | BrC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.CN.C=O.CN1CCOCC1>>BrC1=CC2=C(N=C(S2)N2C(N(CN(C2)C)CC)=O)C=C1 | O=[CH2:7].[CH3:1][CH2:2][NH:3][C:19]([NH:8][c:9]1[n:10][c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]2[s:18]1)=[O:20].[NH2:5][CH3:6]>>[CH3:1][CH2:2][N:3]1[CH2:4][N:5]([CH3:6])[CH2:7][N:8]([c:9]2[n:10][c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][c:17]3[s:18]2)[C:19]1=[O:20] | C=O.CCNC(=O)Nc1nc2ccc(Br)cc2s1.CN | CCN1CN(C)CN(c2nc3ccc(Br)cc3s2)C1=O | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | bdea82356d1d675fe90b0ec07e79d17a706b5b14db216d1856803977c01f0274 | 2bbb8aef114a0ee542edb20042bb6d63f1fdf5f603b0aa000dfbb71b18ea52a0 | O=C1NCNCN1c1nc2ccccc2s1 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[C:3]-[NH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[c:8]1:[#16;a:9]:[c:10]:[c:11]:[#7;a:12]:1.[C;D1;H3:13]-[NH2;D1;+0:14]>>[C;D1;H3:2]-[C:3]-[N;H0;D3;+0:4]1-[C:15]-[N;H0;D3;+0:14](-[C;D1;H3:13])-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[c:8]2:[#16;a:9]:[c:10]:[c:11]:[#7;a:12]:2)-[C:5]-1=[O;D1;H0:6] | 88 | [{"value": 88.0, "product": "BrC1=CC2=C(N=C(S2)N2C(N(CN(C2)C)CC)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-(6-bromo-2-benzothiazolyl)-3-ethylurea, methylamine, formaldehyde, and N-methyl morpholine in a mixed solvent of ethanol and water was reacted to give the desired compound 1.56 g (88%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Urea.Primary amine | Urea.Tertiary amine | null | C1[NH]C[NH]C[NH]1 | C1[NH]C[NH]C[NH]1.c1ccc2scnc2c1 | null | O.C(C)O | null | null | C=O.CCNC(=O)Nc1nc2ccc(Br)cc2s1.CN>O.C(C)O>CCN1CN(C)CN(c2nc3ccc(Br)cc3s2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1d4c968dd1784c18a9903db176fc40d0 | CCNC(=O)Nc1nc2ccc(Br)cc2s1.Nc1cccc(OB(O)O)c1>>CCNC(=O)Nc1nc2ccc(-c3cccc(N)c3)cc2s1 | BrC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.NC=1C=C(C=CC1)OB(O)O.C([O-])(O)=O.[Na+].B(O)(O)O>>NC=1C=C(C=CC1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | Br[c:12]1[cH:11][cH:10][c:9]2[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:22][c:21]2[cH:20]1.OB(O)O[c:13]1[cH:14][cH:15][cH:16][c:17]([NH2:18])[cH:19]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][c:17]([NH2:18])[cH:19]3)[cH:20][c:21]2[s:22]1 | CCNC(=O)Nc1nc2ccc(Br)cc2s1.Nc1cccc(OB(O)O)c1 | CCNC(=O)Nc1nc2ccc(-c3cccc(N)c3)cc2s1 | 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.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=... | CO.CN(C)C=O.O | C-C Coupling | OtherReaction | aa027dae124148b64b7414f562fc7f3a3e2e442b5b0163b02cd26a28f42b2763 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2ccc3ncsc3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1.O-B(-O)-O-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1):[c:13]:[c:14] | 23.4 | [{"value": 23.0, "product": "NC=1C=C(C=CC1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.4, "product": "NC=1C=C(C=CC1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A suspension of 1-(6-bromo-2-benzothiazolyl)-3-ethylurea (0.300 g, 1.00 mmol), 3-aminophenyl boric acid (0.237 g, 1.50 mmol, 1.5 eq), and sodium bicarbonate (0.210 g, 2.50 mmol, 2.5 eq) in 8 mL of mixed solvent DMF/water (5/1) was purged with nitrogen gas. To the mixture, the catalyst Pd(PPh3)4 (0.058 g, 0.05 mmol, 0.0... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2scnc2c1.c1ccccc1 | c1ccc2scnc2c1.c1ccccc1 | c1ccc2scnc2c1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.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=... | 100 | null | CCNC(=O)Nc1nc2ccc(Br)cc2s1.Nc1cccc(OB(O)O)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.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... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-31942f7496ff4aef81cb98e3e09acc55 | CCNC(=O)Nc1nc2ccc(-c3cccc(N)c3)cc2s1.O=C=Nc1ccccc1>>CCNC(=O)Nc1nc2ccc(-c3cccc(NC(=O)Nc4ccccc4)c3)cc2s1 | NC=1C=C(C=CC1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.C(C)N(CC)CC.C1(=CC=CC=C1)N=C=O>>C1(=CC=CC=C1)NC(=O)NC=1C=C(C=CC1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][c:17]([NH2:18])[cH:28]3)[cH:29][c:30]2[s:31]1.[C:19](=[O:20])=[N:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][... | CCNC(=O)Nc1nc2ccc(-c3cccc(N)c3)cc2s1.O=C=Nc1ccccc1 | CCNC(=O)Nc1nc2ccc(-c3cccc(NC(=O)Nc4ccccc4)c3)cc2s1 | null | null | C1(=CC=CC=C1)C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1cccc(-c2ccc3ncsc3c2)c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 44 | [{"value": 44.0, "product": "C1(=CC=CC=C1)NC(=O)NC=1C=C(C=CC1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.0, "product": "C1(=CC=CC=C1)NC(=O)NC=1C=C(C=CC1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A suspension of 1-(6-(3-aminophenyl)-2-benzothiazolyl)-3-ethylurea (0.062 g, 0.20 mmol), triethylamine (0.083 mL, 0.60 mmol, 3.0 eq), and phenyl isocyanate (0.055 mL, 0.50 mmol, 2.5 eq) in 2 mL toluene was stirred at room temperature for about 1 hour. The white precipitation was filtered off, washed with Et2O and MeOH,... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2scnc2c1.c1ccccc1.c1ccccc1 | null | C1(=CC=CC=C1)C | null | 1 | CCNC(=O)Nc1nc2ccc(-c3cccc(N)c3)cc2s1.O=C=Nc1ccccc1>C1(=CC=CC=C1)C>CCNC(=O)Nc1nc2ccc(-c3cccc(NC(=O)Nc4ccccc4)c3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a5f3ce06d6ac4f33ac47c498605c9889 | CCNC(=O)Nc1nc2ccc(-c3cccc(N)c3)cc2s1>>CCNC(=O)Nc1nc2ccc(-c3cn[nH]c3)cc2s1 | NC=1C=C(C=CC1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.BrC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.C([O-])([O-])=O.[Na+].[Na+].CN(C)C=O.O>>N1N=CC(=C1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | c1c[c:13](-[c:12]2[cH:11][cH:10][c:9]3[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:20][c:19]3[cH:18]2)[cH:17][c:14]([NH2:15])c1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][n:15][nH:16][cH:17]3)[cH:18][c:19]2[s:20]1 | CCNC(=O)Nc1nc2ccc(-c3cccc(N)c3)cc2s1 | CCNC(=O)Nc1nc2ccc(-c3cn[nH]c3)cc2s1 | 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 | null | Miscellaneous | OtherReaction | 125e7881eb04548cc0dace591f5e79355c6f46f2637470f7f757777a6d630244 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | c1nc2ccc(-c3cn[nH]c3)cc2s1 | [#16;a:1]:[c:2]:[c:3]:[c:4](-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[NH2;D1;+0:8]):c:c:c:1):[c:9]>>[#16;a:1]:[c:2]:[c:3]:[c:4](-[c;H0;D3;+0:5]1:[cH;D2;+0:7]:[n;H0;D2;+0:8]:[#7;a:10]:[cH;D2;+0:6]:1):[c:9] | 30 | [{"value": 30.0, "product": "N1N=CC(=C1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Similar to the synthesis of 1-(6-(3-aminophenyl)-2-benzothiazolyl)-3-ethylurea, a mixture of 4-pyrazolylboronic pinacolate, 1-(6-bromo-2-benzothiazolyl)-3-ethylurea, sodium carbonate, and Pd(PPh3)4 in DMF/water mixed solvent was reacted to give the desired compound 0.543 g (30%). LC/MS 288.2 (M+1); LC retention time 2.... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccccc1 | c1cn[nH]c1 | c1ccc2scnc2c1.c1cn[nH]c1 | 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 | null | null | CCNC(=O)Nc1nc2ccc(-c3cccc(N)c3)cc2s1>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>CCNC(=O)Nc1nc2ccc(-c3cn[nH]c3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-60da8dac3f014ed1b9238d03474e7f55 | CCNC(=O)Nc1nc2ccc(Br)cc2s1.OB(O)Oc1ccc(Cl)cc1>>CCNC(=O)Nc1nc2ccc(-c3ccc(Cl)cc3)cc2s1 | BrC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.ClC1=CC=C(C=C1)OB(O)O.C([O-])(O)=O.[Na+]>>ClC1=CC=C(C=C1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | Br[c:12]1[cH:11][cH:10][c:9]2[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:22][c:21]2[cH:20]1.OB(O)O[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]3)[cH:20][c:21]2[s:22]1 | CCNC(=O)Nc1nc2ccc(Br)cc2s1.OB(O)Oc1ccc(Cl)cc1 | CCNC(=O)Nc1nc2ccc(-c3ccc(Cl)cc3)cc2s1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CN(C)C=O.O | C-C Coupling | OtherReaction | aa027dae124148b64b7414f562fc7f3a3e2e442b5b0163b02cd26a28f42b2763 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2ccc3ncsc3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1.O-B(-O)-O-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1):[c:13]:[c:14] | 18 | [{"value": 18.0, "product": "ClC1=CC=C(C=C1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Similar to the synthesis of 1-(6-(4-pyrrazolyl)-2-benzothiazolyl)-3-ethylurea, a mixture of 1-(6-bromo-2-benzothiazolyl)-3-ethylurea, 4-chlorophenylboric acid, sodium bicarbonate, and Pd(PPh3)4 in DMF/water mixed solvent (5/1) was reacted to give the desired compound 0.020 g (18%). LC/MS 330 (M−1); LC retention time 2.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2scnc2c1.c1ccccc1 | c1ccc2scnc2c1.c1ccccc1 | c1ccc2scnc2c1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C)C=O.O | null | null | CCNC(=O)Nc1nc2ccc(Br)cc2s1.OB(O)Oc1ccc(Cl)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C)C=O.O>CCNC(=O)Nc1nc2ccc(-c3ccc(Cl)cc3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-539abe6e916e46699d709602a0ec92f3 | CCNC(=O)Nc1nc2ccc(-c3cccc(N)c3)cc2s1.Cc1cccc(N=C=O)c1>>CCNC(=O)Nc1nc2ccc(-c3cccc(NC(=O)Nc4cccc(C)c4)c3)cc2s1 | NC=1C=C(C=CC1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.C(C)N(CC)CC.C1(=CC(=CC=C1)N=C=O)C.C1(=CC=CC=C1)NC(=O)NC=1C=C(C=CC1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1>>C1(=CC(=CC=C1)NC(=O)NC=1C=C(C=CC1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1)C | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][c:17]([NH2:18])[cH:29]3)[cH:30][c:31]2[s:32]1.[C:19](=[O:20])=[N:21][c:22]1[cH:23][cH:24][cH:25][c:26]([CH3:27])[cH:28]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14... | CCNC(=O)Nc1nc2ccc(-c3cccc(N)c3)cc2s1.Cc1cccc(N=C=O)c1 | CCNC(=O)Nc1nc2ccc(-c3cccc(NC(=O)Nc4cccc(C)c4)c3)cc2s1 | null | null | C1(=CC=CC=C1)C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1cccc(-c2ccc3ncsc3c2)c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 26 | [{"value": 26.0, "product": "C1(=CC(=CC=C1)NC(=O)NC=1C=C(C=CC1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Similar to the synthesis of 1-(6-(3-phenylaminocarbonylaminophenyl)-2-benzothiazolyl)-3-ethylurea, a mixture of 1-(6-(3-aminophenyl)-2-benzothiazolyl)-3-ethylurea, triethylamine, and 3-tolyl isocyanate in toluene was reacted to give the desired compound 0.023 g (26%). LC/MS 446.2 (M+1); LC retention time 3.76 min.
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2scnc2c1.c1ccccc1.c1ccccc1 | null | C1(=CC=CC=C1)C | null | null | CCNC(=O)Nc1nc2ccc(-c3cccc(N)c3)cc2s1.Cc1cccc(N=C=O)c1>C1(=CC=CC=C1)C>CCNC(=O)Nc1nc2ccc(-c3cccc(NC(=O)Nc4cccc(C)c4)c3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8af57543031d410a83801cfb7baaad6c | CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.O=C=Nc1ccccc1F>>CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)Nc3ccccc3F)cc2s1 | NCCC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.C(C)N(CC)CC.FC1=C(C=CC=C1)N=C=O>>FC1=C(C=CC=C1)NC(=O)NCCC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][CH2:16][NH2:17])[cH:28][c:29]2[s:30]1.[C:18](=[O:19])=[N:20][c:21]1[cH:22][cH:23][cH:24][cH:25][c:26]1[F:27]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[CH2:15][CH2:16][... | CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.O=C=Nc1ccccc1F | CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)Nc3ccccc3F)cc2s1 | null | null | CN(C)C=O | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCCC(=O)c1ccc2ncsc2c1)Nc1ccccc1 | [NH2;D1;+0:1]-[C:2]-[C:3]-[C:4]=[O;D1;H0:5].[O;D1;H0:6]=[C;H0;D2;+0:7]=[N;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[O;D1;H0:5]=[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-[C;H0;D3;+0:7](=[O;D1;H0:6])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 26 | [{"value": 26.0, "product": "FC1=C(C=CC=C1)NC(=O)NCCC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Similar to the synthesis of Example 249, a mixture of 1-(6-(3-aminopropanoyl)-2-benzothiazolyl)-3-ethylurea, triethylamine and 2-fluorophenyl isocyanate in DMF was reacted to give the desired compound 0.022 g (26%). LC/MS 430.01 (M+1); LC retention time 2.89 min.
Conditions: See reaction.notes.procedure_details.
Workup... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2scnc2c1.c1ccccc1 | null | CN(C)C=O | null | null | CCNC(=O)Nc1nc2ccc(C(=O)CCN)cc2s1.O=C=Nc1ccccc1F>CN(C)C=O>CCNC(=O)Nc1nc2ccc(C(=O)CCNC(=O)Nc3ccccc3F)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a17813f0e3914b2492892bf738b5e7ad | CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)CC2.NC(=S)c1cccnc1>>CCNC(=O)Nc1nc2c(s1)-c1nc(-c3cccnc3)sc1CC2 | BrC1C(C2=C(N=C(S2)NC(=O)NCC)CC1)=O.C(C1=CN=CC=C1)(=S)N>>C(C)NC(=O)NC=1SC2=C(N1)CCC1=C2N=C(S1)C=1C=NC=CC1 | O=[C:12]1[c:10]2[c:9]([n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:11]2)[CH2:24][CH2:23][CH:22]1Br.[NH2:13][C:14]([c:15]1[cH:16][cH:17][cH:18][n:19][cH:20]1)=[S:21]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:10]([s:11]1)-[c:12]1[n:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][n:19][cH:20]3)[s:21][c:... | CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)CC2.NC(=S)c1cccnc1 | CCNC(=O)Nc1nc2c(s1)-c1nc(-c3cccnc3)sc1CC2 | null | null | C(CC)O | Aromatic Heterocycle Formation | OtherReaction | a2f2eb51403d9a05fc98811e474b0ec19c56935250d376f54b58edbc25453242 | 2f7d3f716d5548dca0427566e115a085daf8db6f0505088ac8ec29cdf098ce85 | c1cncc(-c2nc3c(s2)CCc2ncsc2-3)c1 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-[c:4]2:[#7;a:5]:[c:6](-[#7:7]-[C:8]=[O;D1;H0:9]):[#16;a:10]:[c;H0;D3;+0:11]:2-[C;H0;D3;+0:12]-1=O.[NH2;D1;+0:13]-[C;H0;D3;+0:14](=[S;H0;D1;+0:15])-[c;H0;D3;+0:16]1:[c:17]:[c:18]:[c:19]:[#7;a:20]:[c:21]:1>>[O;D1;H0:9]=[C:8]-[#7:7]-[c:6]1:[#16;a:10]:[c;H0;D3;+0:11]2:[c:4](:[#7;a:5]:1)-[C:3]-[... | 36 | [{"value": 36.0, "product": "C(C)NC(=O)NC=1SC2=C(N1)CCC1=C2N=C(S1)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.4, "product": "C(C)NC(=O)NC=1SC2=C(N1)CCC1=C2N=C(S1)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | null | null | A suspension of N-(6-bromo-7-oxo-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)-N′-ethylurea (25 mg, 0.079 mmol) and thionicotinamide (11 mg, 0.079 mmol) in n-propanol (0.4 mL) was heated to about 105° C. for about 16 hrs. The reaction mixture was concentrated in vacuo and the residual crude material was purified by prepara... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Thioamide | null | c1nc2c(s1)CCCC2 | c1nc2c(s1)CCc1ncsc12 | c1ccncc1.c1nc2c(s1)CCc1ncsc12 | HBr | C(CC)O | 105 | null | CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)CC2.NC(=S)c1cccnc1>C(CC)O>CCNC(=O)Nc1nc2c(s1)-c1nc(-c3cccnc3)sc1CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-990155086c5549828f0ac2fa7edc056a | CCNC(=O)Nc1nc2c(s1)-c1nc(-c3cccnc3)sc1CC2>>CCNC(=O)Nc1nc2ccc3sc(-c4cccnc4)nc3c2s1 | C(C)NC(=O)NC=1SC2=C(N1)CCC1=C2N=C(S1)C=1C=NC=CC1.C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N>>C(C)NC(=O)NC=1SC2=C(N1)C=CC1=C2N=C(S1)C=1C=NC=CC1 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:23]([s:24]1)-[c:22]1[c:12]([s:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][n:19][cH:20]3)[n:21]1)[CH2:11][CH2:10]2>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]3[s:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][n:19][cH:20]4)[n:21][c:22]3[c:... | CCNC(=O)Nc1nc2c(s1)-c1nc(-c3cccnc3)sc1CC2 | CCNC(=O)Nc1nc2ccc3sc(-c4cccnc4)nc3c2s1 | null | null | C1(=CC=CC=C1)C | Oxidation | OtherReaction | 6cc44f1250f81f32b38c699e23b33fc31507bf469779f170eb8f74a5ac9acf35 | 82a3692de44364afcfd8cc4460435180e0752c31812bf6008d75e02664a32947 | c1cncc(-c2nc3c(ccc4ncsc43)s2)c1 | [#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5]1:[#16;a:6]:[c;H0;D3;+0:7]2:[c:8](:[#7;a:9]:1)-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[c:12]1:[#16;a:13]:[c:14](-[c:15]:[c:16]:[#7;a:17]):[#7;a:18]:[c;H0;D3;+0:19]:1-2>>[#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5]1:[#16;a:6]:[c;H0;D3;+0:7]2:[c:8](:[#7;a:9]:1):[cH;D2;+0:10]:[cH;D2;+0:11]:[c:12]1... | 30.1 | [{"value": 30.0, "product": "C(C)NC(=O)NC=1SC2=C(N1)C=CC1=C2N=C(S1)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.1, "product": "C(C)NC(=O)NC=1SC2=C(N1)C=CC1=C2N=C(S1)C=1C=NC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 35 | CELSIUS | null | null | A suspension of N-ethyl-N′-[7-(3-pyridyl)-4,5-dihydro[1,3]thiazolo[4′,5′: 3,4]benzo[d]-[1,3]thiazol-2-yl]urea (10 mg, 0.028 mmol) and DDQ (13 mg, 0.056 mmol) in toluene (1 mL) was heated to about 35° C. for about 3 hrs. The reaction mixture was concentrated in vacuo and purified by preparative HPLC. 3 mg (30%) pure pro... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1nc2c(s1)CCc1ncsc12 | c1nc2c(ccc3ncsc32)s1 | c1nc2c(ccc3ncsc32)s1.c1ccncc1 | null | C1(=CC=CC=C1)C | 35 | null | CCNC(=O)Nc1nc2c(s1)-c1nc(-c3cccnc3)sc1CC2>C1(=CC=CC=C1)C>CCNC(=O)Nc1nc2ccc3sc(-c4cccnc4)nc3c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ea8233a5c256454ba3ea6ba2c519a36d | CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)CC2.NC(=S)Nc1ccc(Br)cc1>>CCNC(=O)Nc1nc2c(s1)-c1nc(Nc3ccc(Br)cc3)sc1CC2 | BrC1C(C2=C(N=C(S2)NC(=O)NCC)CC1)=O.BrC1=CC=C(C=C1)NC(=S)N>>BrC1=CC=C(NC=2SC3=C(C4=C(N=C(S4)NC(=O)NCC)CC3)N2)C=C1 | O=[C:12]1[c:10]2[c:9]([n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:11]2)[CH2:26][CH2:25][CH:24]1Br.[NH2:13][C:14]([NH:15][c:16]1[cH:17][cH:18][c:19]([Br:20])[cH:21][cH:22]1)=[S:23]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:10]([s:11]1)-[c:12]1[n:13][c:14]([NH:15][c:16]3[cH:17][cH:18][c:19]([B... | CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)CC2.NC(=S)Nc1ccc(Br)cc1 | CCNC(=O)Nc1nc2c(s1)-c1nc(Nc3ccc(Br)cc3)sc1CC2 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | 03016e5ba09627f86c3cfb100e325f44ad6cb3c35403a92a8dc24b7eb7050d90 | 63720916d593fffe9896c07168d54e21e0baac636524cc58f558ccbd57d164ad | c1ccc(Nc2nc3c(s2)CCc2ncsc2-3)cc1 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-[c:4]2:[#7;a:5]:[c:6](-[#7:7]-[C:8]=[O;D1;H0:9]):[#16;a:10]:[c;H0;D3;+0:11]:2-[C;H0;D3;+0:12]-1=O.[NH2;D1;+0:13]-[C;H0;D3;+0:14](=[S;H0;D1;+0:15])-[#7:16]-[c:17]>>[O;D1;H0:9]=[C:8]-[#7:7]-[c:6]1:[#16;a:10]:[c;H0;D3;+0:11]2:[c:4](:[#7;a:5]:1)-[C:3]-[C:2]-[c;H0;D3;+0:1]1:[s;H0;D2;+0:15]:[c;H0... | null | [] | 65 | CELSIUS | null | null | A suspension of N-(6-bromo-7-oxo-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)-N′-ethylurea (50 mg, 0.16 mmol) and 4-bromo-phenyl-thiourea (36 mg, 0.16 mmol) in THF (1.0 mL) was heated to about 65° C. for about 1.5 hrs. The reaction mixture was pumped down and used in the next step without further purification.
Conditions:... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Thiourea | null | c1nc2c(s1)CCCC2 | c1nc2c(s1)CCc1ncsc12 | c1ccccc1.c1nc2c(s1)CCc1ncsc12 | HBr | C1CCOC1 | 65 | null | CCNC(=O)Nc1nc2c(s1)C(=O)C(Br)CC2.NC(=S)Nc1ccc(Br)cc1>C1CCOC1>CCNC(=O)Nc1nc2c(s1)-c1nc(Nc3ccc(Br)cc3)sc1CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-108f08c279ff47c1a94c99a2e3501eb7 | CCNC(=O)Nc1nc2c(s1)-c1nc(Nc3ccc(Br)cc3)sc1CC2>>CCNC(=O)Nc1nc2ccc3sc(Nc4ccc(Br)cc4)nc3c2s1 | BrC1=CC=C(NC=2SC3=C(C4=C(N=C(S4)NC(=O)NCC)CC3)N2)C=C1.C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N>>BrC1=CC=C(NC=2SC3=C(C4=C(N=C(S4)NC(=O)NCC)C=C3)N2)C=C1 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:25]([s:26]1)-[c:24]1[c:12]([s:13][c:14]([NH:15][c:16]3[cH:17][cH:18][c:19]([Br:20])[cH:21][cH:22]3)[n:23]1)[CH2:11][CH2:10]2>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]3[s:13][c:14]([NH:15][c:16]4[cH:17][cH:18][c:19]([Br:20])[c... | CCNC(=O)Nc1nc2c(s1)-c1nc(Nc3ccc(Br)cc3)sc1CC2 | CCNC(=O)Nc1nc2ccc3sc(Nc4ccc(Br)cc4)nc3c2s1 | null | null | C1(=CC=CC=C1)C | Oxidation | OtherReaction | 6cc44f1250f81f32b38c699e23b33fc31507bf469779f170eb8f74a5ac9acf35 | 82a3692de44364afcfd8cc4460435180e0752c31812bf6008d75e02664a32947 | c1ccc(Nc2nc3c(ccc4ncsc43)s2)cc1 | [#7:1]-[c:2]1:[#16;a:3]:[c:4]2:[c;H0;D3;+0:5](:[#7;a:6]:1)-[c;H0;D3;+0:7]1:[#16;a:8]:[c:9](-[#7:10]-[C:11](-[#7:12])=[O;D1;H0:13]):[#7;a:14]:[c:15]:1-[CH2;D2;+0:16]-[CH2;D2;+0:17]-2>>[#7:1]-[c:2]1:[#16;a:3]:[c:4]2:[cH;D2;+0:17]:[cH;D2;+0:16]:[c:15]3:[#7;a:14]:[c:9](-[#7:10]-[C:11](-[#7:12])=[O;D1;H0:13]):[#16;a:8]:[c;H... | null | [] | 20 | CELSIUS | 2 | HOUR | To a suspension of N-[7-(4-bromoanilino)-4,5-dihydro[1,3]thiazolo[4′,5′: 3,4]benzo[d][1,3]thiazol-2-yl]-N′-ethylurea (27 mg, 0.060 mmol) in toluene (2.0 mL) was added DDQ (28 mg, 0.125 mmol). The reaction mixture was stirred at about 20° C. for about 2 hrs. The reaction mixture was pumped down in vacuo and purified by ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1nc2c(s1)CCc1ncsc12 | c1nc2c(ccc3ncsc32)s1 | c1nc2c(ccc3ncsc32)s1.c1ccccc1 | null | C1(=CC=CC=C1)C | 20 | 2 | CCNC(=O)Nc1nc2c(s1)-c1nc(Nc3ccc(Br)cc3)sc1CC2>C1(=CC=CC=C1)C>CCNC(=O)Nc1nc2ccc3sc(Nc4ccc(Br)cc4)nc3c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-18fdaa5a2062445dbc2788aa4294d857 | C=O.CCNC(=O)Nc1nc2c(s1)C(=O)CCC2.CN>>CCN1CN(C)CN(c2nc3c(s2)C(=O)CCC3)C1=O | C(C)NC(=O)NC=1SC2=C(N1)CCCC2=O.C=O.CN.CN1CCOCC1>>C(C)N1C(N(CN(C1)C)C=1SC2=C(N1)CCCC2=O)=O | O=[CH2:7].[CH3:1][CH2:2][NH:3][C:19]([NH:8][c:9]1[n:10][c:11]2[c:12]([s:13]1)[C:14](=[O:15])[CH2:16][CH2:17][CH2:18]2)=[O:20].[NH2:5][CH3:6]>>[CH3:1][CH2:2][N:3]1[CH2:4][N:5]([CH3:6])[CH2:7][N:8]([c:9]2[n:10][c:11]3[c:12]([s:13]2)[C:14](=[O:15])[CH2:16][CH2:17][CH2:18]3)[C:19]1=[O:20] | C=O.CCNC(=O)Nc1nc2c(s1)C(=O)CCC2.CN | CCN1CN(C)CN(c2nc3c(s2)C(=O)CCC3)C1=O | null | null | CCO.O | Heteroatom Alkylation and Arylation | OtherReaction | bdea82356d1d675fe90b0ec07e79d17a706b5b14db216d1856803977c01f0274 | 2bbb8aef114a0ee542edb20042bb6d63f1fdf5f603b0aa000dfbb71b18ea52a0 | O=C1CCCc2nc(N3CNCNC3=O)sc21 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[C:3]-[NH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[c:8]1:[#16;a:9]:[c:10](:[c:11]:[#7;a:12]:1)-[C:13]=[O;D1;H0:14].[C;D1;H3:15]-[NH2;D1;+0:16]>>[C;D1;H3:2]-[C:3]-[N;H0;D3;+0:4]1-[C:17]-[N;H0;D3;+0:16](-[C;D1;H3:15])-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[c:8]2:[#16;a:9]:[c:10](:[c:11]:[#7;a:12]:2)... | 100.9 | [{"value": 100.9, "product": "C(C)N1C(N(CN(C1)C)C=1SC2=C(N1)CCCC2=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a suspension of N-ethyl-N′-(7-oxo-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)urea (10.0 g, 41.79 mmol) in EtOH/H2O (1/1, 300 mL) were added formaldehyde (37 wt % in H2O, 20.4 g, 417.87 mmol), methylamine (40 wt % in H2O, 10.8 mL, 125.37 mmol) and N-methylmorpholine (11.8 mL, 83.6 mmol). The suspension was heated to ab... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Urea.Primary amine | Urea.Tertiary amine | null | C1[NH]C[NH]C[NH]1 | C1[NH]C[NH]C[NH]1.c1nc2c(s1)CCCC2 | null | CCO.O | 60 | null | C=O.CCNC(=O)Nc1nc2c(s1)C(=O)CCC2.CN>CCO.O>CCN1CN(C)CN(c2nc3c(s2)C(=O)CCC3)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2df8a4191bd44591b7d0af914e3af49b | CCNC(=O)Nc1nc2c(s1)-c1[nH]ccc1CC2.N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O>>CCNC(=O)Nc1nc2c(s1)-c1c(ccn1C)CC2 | S1C(=NC=2CCC=3C=CNC3C21)NC(=O)NCC.C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N>>C(C)NC(=O)NC=1SC2=C(CCC=3C=CN(C23)C)N1 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:10]([s:11]1)-[c:12]1[c:13]([cH:14][cH:15][nH:16]1)[CH2:18][CH2:19]2.N#CC1=C([C:17]#N)C(=O)C(Cl)=C(Cl)C1=O>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:10]([s:11]1)-[c:12]1[c:13]([cH:14][cH:15][n:16]1[CH3:17])[CH2:18][CH2:19]2 | CCNC(=O)Nc1nc2c(s1)-c1[nH]ccc1CC2.N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O | CCNC(=O)Nc1nc2c(s1)-c1c(ccn1C)CC2 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 84baf968a077024b89fadfa4bd237c797aafaae6872f5075f083b59f5f6b7a01 | 2d200faa4c3734aabbf17905a35fb1786eb1df307ed4e3388becce1f621bbca2 | c1cc2c([nH]1)-c1scnc1CC2 | Cl-C1=C(-Cl)-C(=O)-C(-[C;H0;D2;+0:1]#N)=C(-C#N)-C-1=O.[#16;a:2]:[c:3](:[c:4]:[#7;a:5])-[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[#16;a:2]:[c:3](:[c:4]:[#7;a:5])-[c:6]1:[c:7]:[c:8]:[c:9]:[n;H0;D3;+0:10]:1-[CH3;D1;+0:1] | null | [] | 45 | CELSIUS | 4 | HOUR | To a suspension of N-(5,8-dihydro-4H-[1,3]thiazolo[4,5-g]indol-2-yl)-N′-ethylurea in toluene is added DDQ (1.1 eq.). The reaction mixture is stirred at about 45° C. for about 4 hrs. The reaction mixture is pumped down and the crude material is purified by preparative HPLC.
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Alkenyl halide.Ketone.Ketone.Nitrile.Nitrile | null | c1cc2c(n1)c1scnc1CC2.C1=CCC=CC1 | c1nc2c(s1)c1nccc1CC2 | c1nc2c(s1)c1nccc1CC2 | Other | C1(=CC=CC=C1)C | 45 | 4 | CCNC(=O)Nc1nc2c(s1)-c1[nH]ccc1CC2.N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O>C1(=CC=CC=C1)C>CCNC(=O)Nc1nc2c(s1)-c1c(ccn1C)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5a0dc76b8b9c408797b9d2afd2580814 | CCNC(=O)Nc1nc2c(s1)-c1[nH]ccc1CC2>>CCNC(=O)Nc1nc2ccc3cc[nH]c3c2s1 | S1C(=NC=2CCC=3C=CNC3C21)NC(=O)NCC.C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N>>C(C)NC(=O)NC=1SC2=C(C=CC=3C=CNC23)N1 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:17]([s:18]1)-[c:16]1[c:12]([cH:13][cH:14][nH:15]1)[CH2:11][CH2:10]2>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]3[cH:13][cH:14][nH:15][c:16]3[c:17]2[s:18]1 | CCNC(=O)Nc1nc2c(s1)-c1[nH]ccc1CC2 | CCNC(=O)Nc1nc2ccc3cc[nH]c3c2s1 | null | null | C1(=CC=CC=C1)C | Oxidation | OtherReaction | b802f857f431ab302609f735d487880992dbf3e5284eb2e4c91a3a3d1c79f041 | 82a3692de44364afcfd8cc4460435180e0752c31812bf6008d75e02664a32947 | c1cc2ccc3ncsc3c2[nH]1 | [#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5]1:[#16;a:6]:[c;H0;D3;+0:7]2:[c:8](:[#7;a:9]:1)-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[c:12]1:[c:13]:[c:14]:[#7;a:15]:[c;H0;D3;+0:16]:1-2>>[#7:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5]1:[#16;a:6]:[c;H0;D3;+0:7]2:[c:8](:[#7;a:9]:1):[cH;D2;+0:10]:[cH;D2;+0:11]:[c:12]1:[c:13]:[c:14]:[#7;a:15]:[c;H0... | null | [] | 45 | CELSIUS | 4 | HOUR | To a suspension of N-(5,8-dihydro-4H-[1,3]thiazolo[4,5-g]indol-2-yl)-N′-ethylurea (81 mg, 0.308 mmol) in toluene (3.5 mL) was added DDQ (78 mg, 0.34 mmol). The reaction mixture was stirred at about 45° C. for about 4 hrs. The reaction mixture was pumped down and the crude material was purified by preparative HPLC. 3 mg... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc2c(n1)c1scnc1CC2 | c1cc2ccc3ncsc3c2n1 | c1cc2ccc3ncsc3c2n1 | null | C1(=CC=CC=C1)C | 45 | 4 | CCNC(=O)Nc1nc2c(s1)-c1[nH]ccc1CC2>C1(=CC=CC=C1)C>CCNC(=O)Nc1nc2ccc3cc[nH]c3c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b6a64fb918f4c86bf8bb7e50346ffdf | CCNC(=O)Nc1nc2c(s1)C(=O)CCC2.Sc1ccccc1.Sc1ccccc1>>CCNC(=O)Nc1nc2c(s1)C(Sc1ccccc1)(Sc1ccccc1)CCC2 | C1(=CC=CC=C1)S.C(C)NC(=O)NC=1SC2=C(N1)CCCC2=O.C1(=CC=CC=C1)S.Cl>>C1(=CC=CC=C1)SC1(CCCC=2N=C(SC21)NC(=O)NCC)SC2=CC=CC=C2 | O=[C:12]1[c:10]2[c:9]([n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:11]2)[CH2:29][CH2:28][CH2:27]1.[SH:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.[SH:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:10]([s:11]1)[C:12]([S:13][c:14]1[cH:15][cH:16][cH:1... | CCNC(=O)Nc1nc2c(s1)C(=O)CCC2.Sc1ccccc1.Sc1ccccc1 | CCNC(=O)Nc1nc2c(s1)C(Sc1ccccc1)(Sc1ccccc1)CCC2 | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | 4747cb78cac2aad592b3ca44c239eed0cadcb8b26140e70d1151774c59006c17 | 1d9d6ee9d77442dc1bde18cc35949be811ff28784f0810fab70dac59f3531b1b | c1ccc(SC2(Sc3ccccc3)CCCc3ncsc32)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[c:5]2:[#7;a:6]:[c:7]:[#16;a:8]:[c:9]:2-1.[SH;D1;+0:10]-[c:11](:[c:12]):[c:13].[SH;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[c:16]:[c:15](-[S;H0;D2;+0:14]-[C;H0;D4;+0:1]1(-[S;H0;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:2]-[C:3]-[C:4]-[c:5]2:[#7;a:6]:[c:7]:[#16;a:8]:[c:9]:2-1):[c:17] | 200.4 | [{"value": 200.4, "product": "C1(=CC=CC=C1)SC1(CCCC=2N=C(SC21)NC(=O)NCC)SC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 2 | HOUR | A suspension of N-ethyl-N′-(7-oxo-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)urea (1.0 g, 4.18 mmol) and thiophenol (0.59 mL, 4.74 mmol) in EtOH (20 mL) was saturated with HCl (g) at about 0° C. The reaction mixture was stirred at about 20° C. for about 2 hrs then a second portion of thiophenol (0.59 mL, 4.74 mmol) was a... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aromatic thiol.Aromatic thiol | Monosulfide.Monosulfide | c1nc2c(s1)CCCC2 | c1nc2c(s1)CCCC2 | c1ccccc1.c1ccccc1.c1nc2c(s1)CCCC2 | HO- | CCO | 20 | 2 | CCNC(=O)Nc1nc2c(s1)C(=O)CCC2.Sc1ccccc1.Sc1ccccc1>CCO>CCNC(=O)Nc1nc2c(s1)C(Sc1ccccc1)(Sc1ccccc1)CCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f52c1f5594b74389a752e81d2ba57891 | CCNC(=O)Nc1nc2c(s1)C(Sc1ccccc1)(Sc1ccccc1)CCC2>>CCNC(=O)Nc1nc2c(s1)C(Sc1ccccc1)=CCC2 | C1(=CC=CC=C1)SC1(CCCC=2N=C(SC21)NC(=O)NCC)SC2=CC=CC=C2.C1CCC2=NCCCN2CC1>>C(C)NC(=O)NC=1SC2=C(N1)CCC=C2SC2=CC=CC=C2 | c1ccc(S[C:12]2([S:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[c:10]3[c:9]([n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:11]3)[CH2:22][CH2:21][CH2:20]2)cc1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:10]([s:11]1)[C:12]([S:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)=[CH:20][CH2:21][CH2:22]... | CCNC(=O)Nc1nc2c(s1)C(Sc1ccccc1)(Sc1ccccc1)CCC2 | CCNC(=O)Nc1nc2c(s1)C(Sc1ccccc1)=CCC2 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | e423e2a86cc1dd1035cd2cbe91e6e3244b11d516e853e57c0ce703ec5d0c94ef | 187a3a019075e0537d9f98fccd322496a7034ae6952c500be4d0cad597e6f44b | C1=C(Sc2ccccc2)c2scnc2CC1 | [c:1]-[#16:2]-[C;H0;D4;+0:3]1(-S-c2:c:c:c:c:c:2)-[CH2;D2;+0:4]-[C:5]-[C:6]-[c:7]2:[#7;a:8]:[c:9]:[#16;a:10]:[c:11]:2-1>>[c:1]-[#16:2]-[C;H0;D3;+0:3]1=[CH;D2;+0:4]-[C:5]-[C:6]-[c:7]2:[#7;a:8]:[c:9]:[#16;a:10]:[c:11]:2-1 | null | [] | 20 | CELSIUS | 30 | MINUTE | To a suspension of N-[7,7-di(phenylsulfanyl)-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl]-N′-ethylurea (700 mg, 1.59 mmol) in THF (14.0 mL) was added DBU (0.36 mL, 2.38 mmol). The reaction mixture was stirred at about 20° C. for about 30 min. The reaction was concentrated in vacuo. The residual yellow oil was taken up in ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Monosulfide | Monosulfide | c1ccccc1.c1nc2c(s1)CCCC2 | C1=Cc2scnc2CC1 | c1ccccc1.C1=Cc2scnc2CC1 | Other | C1CCOC1 | 20 | 0.5 | CCNC(=O)Nc1nc2c(s1)C(Sc1ccccc1)(Sc1ccccc1)CCC2>C1CCOC1>CCNC(=O)Nc1nc2c(s1)C(Sc1ccccc1)=CCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-955b7113daa34b80b77e74e52f6c7686 | CCNC(=O)Nc1nc2c(s1)C(Sc1ccccc1)=CCC2>>CCNC(=O)Nc1nc2cccc(Sc3ccccc3)c2s1 | C(C)NC(=O)NC=1SC2=C(N1)CCC=C2SC2=CC=CC=C2.C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N>>C(C)NC(=O)NC=1SC2=C(N1)C=CC=C2SC2=CC=CC=C2 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:21]([s:22]1)[C:13]([S:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)=[CH:12][CH2:11][CH2:10]2>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][cH:12][c:13]([S:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]2[s:22]1 | CCNC(=O)Nc1nc2c(s1)C(Sc1ccccc1)=CCC2 | CCNC(=O)Nc1nc2cccc(Sc3ccccc3)c2s1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 2752eee2eb9332d422f07cd7f7d633729f7729d0e17a7bfc110572aa820f04b9 | 04aedd72d47e3929bd14c1ad18abeeed4729294a1bf9373b286439de2d28df92 | c1ccc(Sc2cccc3ncsc23)cc1 | [c:1]-[#16:2]-[C;H0;D3;+0:3]1=[CH;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7]2:[#7;a:8]:[c:9]:[#16;a:10]:[c:11]:2-1>>[c:1]-[#16:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[c:7]2:[#7;a:8]:[c:9]:[#16;a:10]:[c:11]:2:1 | null | [] | 20 | CELSIUS | 2 | HOUR | To a mixture of N-ethyl-N′-[7-(phenylsulfanyl)-4,5-dihydro-1,3-benzothiazol-2-yl]urea (crude product from the previous reaction, 1.59 mmol) in toluene (35.0 mL) was added DDQ (500 mg, 2.17 mmol). The reaction mixture was stirred at about 20° C. for about 2 hrs. The toluene was removed in vacuo and the crude material wa... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Monosulfide | C1=Cc2scnc2CC1 | c1ccc2scnc2c1 | c1ccc2scnc2c1.c1ccccc1 | null | C1(=CC=CC=C1)C | 20 | 2 | CCNC(=O)Nc1nc2c(s1)C(Sc1ccccc1)=CCC2>C1(=CC=CC=C1)C>CCNC(=O)Nc1nc2cccc(Sc3ccccc3)c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ac6888f33d2349549c68bc6416e95d15 | CCNC(=O)Nc1nc2cccc(Sc3ccccc3)c2s1.O=C(OO)c1cccc(Cl)c1>>CCNC(=O)Nc1nc2cccc(S(=O)c3ccccc3)c2s1 | C(C)NC(=O)NC=1SC2=C(N1)C=CC=C2SC2=CC=CC=C2.C1=CC(=CC(=C1)Cl)C(=O)OO>>C(C)NC(=O)NC=1SC2=C(N1)C=CC=C2S(=O)C2=CC=CC=C2 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][cH:12][c:13]([S:14][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[c:22]2[s:23]1.O=C(O[OH:15])c1cccc(Cl)c1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][cH:12][c:13]([S:14](=[O:15])[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[... | CCNC(=O)Nc1nc2cccc(Sc3ccccc3)c2s1.O=C(OO)c1cccc(Cl)c1 | CCNC(=O)Nc1nc2cccc(S(=O)c3ccccc3)c2s1 | null | null | C(Cl)Cl | Oxidation | Sulfanyl to sulfinyl_peroxide | 95b5106b07a173d8eafc1c9c8a6c938befe131c3d1caaf5886529b7aee55ea9d | 7652b53bb02130dccfe4b1e8905d7f3db7f05ff3a95a0003c1bab09b1ad4083e | O=S(c1ccccc1)c1cccc2ncsc12 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[c:2]:[c:3](-[S;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8]1:[#16;a:9]:[c:10]:[#7;a:11]:[c:12]:1>>[O;H0;D1;+0:1]=[S;H0;D3;+0:4](-[c:3](:[c:2]):[c:8]1:[#16;a:9]:[c:10]:[#7;a:11]:[c:12]:1)-[c:5](:[c:6]):[c:7] | 38.6 | [{"value": 29.0, "product": "C(C)NC(=O)NC=1SC2=C(N1)C=CC=C2S(=O)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.6, "product": "C(C)NC(=O)NC=1SC2=C(N1)C=CC=C2S(=O)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1.5 | HOUR | To a suspension of N-ethyl-N′-[7-(phenylsulfanyl)-1,3-benzothiazol-2-yl]urea (107 mg, 0.32 mmol) in CH2Cl2 (5 mL) was added MCPBA (60 mg, 0.24 mmol, 70%). The reaction mixture was stirred at about 20° C. for about 1.5 hrs. The reaction mixture was then concentrated in vacuo. The crude reaction mixture was purified by f... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfoxide | c1ccccc1 | null | c1ccc2scnc2c1.c1ccccc1 | HCl | C(Cl)Cl | 20 | 1.5 | CCNC(=O)Nc1nc2cccc(Sc3ccccc3)c2s1.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>CCNC(=O)Nc1nc2cccc(S(=O)c3ccccc3)c2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8cc7371e38f3460581b5e22886eb5510 | C1CNCCN1.O=C(NCCCCl)Nc1nc2ccc(Br)cc2s1>>O=C(NCCCN1CCNCC1)Nc1nc2ccc(Br)cc2s1 | BrC1=CC2=C(N=C(S2)NC(=O)NCCCCl)C=C1.N1CCNCC1>>BrC1=CC2=C(N=C(S2)NC(=O)NCCCN2CCNCC2)C=C1 | [NH:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1.Cl[CH2:6][CH2:5][CH2:4][NH:3][C:2](=[O:1])[NH:13][c:14]1[n:15][c:16]2[cH:17][cH:18][c:19]([Br:20])[cH:21][c:22]2[s:23]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1)[NH:13][c:14]1[n:15][c:16]2[cH:17][cH:18][c:19]([Br:20])[cH:21][c:22]... | C1CNCCN1.O=C(NCCCCl)Nc1nc2ccc(Br)cc2s1 | O=C(NCCCN1CCNCC1)Nc1nc2ccc(Br)cc2s1 | null | null | C1CCOC1.CCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 61ec49e5207aa33ebff7094bb66b1d997d4af14524931a8b3643ef7a94219a9a | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(NCCCN1CCNCC1)Nc1nc2ccccc2s1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | 55 | CELSIUS | null | null | To a mixture of N-(6-bromo-1,3-benzothiazol-2-yl)-N′-(3-chloropropyl)urea (100 mg, 0.287 mmol) in THF/EtOH (0.50/0.25 mL) was added piperazine (247 mg, 2.87 mmol). The reaction mixture was heated to about 55° C. for about 16 hrs. The crude reaction mixture was pumped down and purified by flash chromatography on SiO2.
C... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCCN1 | C1C[NH]CCN1 | C1C[NH]CCN1.c1ccc2scnc2c1 | HCl | C1CCOC1.CCO | 55 | null | C1CNCCN1.O=C(NCCCCl)Nc1nc2ccc(Br)cc2s1>C1CCOC1.CCO>O=C(NCCCN1CCNCC1)Nc1nc2ccc(Br)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eeb2af849bb244f29f28bc6c0698016c | CCOC(=O)CCCNC(=O)Nc1nc2ccc(Br)cc2s1>>O=C(O)CCCNC(=O)Nc1nc2ccc(Br)cc2s1 | Cl.BrC1=CC2=C(N=C(S2)NC(=O)NCCCC(=O)OCC)C=C1.[OH-].[Na+]>>BrC1=CC2=C(N=C(S2)NC(=O)NCCCC(=O)O)C=C1 | CC[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[NH:10][c:11]1[n:12][c:13]2[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]2[s:20]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:9])[NH:10][c:11]1[n:12][c:13]2[cH:14][cH:15][c:16]([Br:17])[cH:18][c:19]2[s:20]1 | CCOC(=O)CCCNC(=O)Nc1nc2ccc(Br)cc2s1 | O=C(O)CCCNC(=O)Nc1nc2ccc(Br)cc2s1 | null | null | C1CCOC1.CCO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2scnc2c1 | 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] | 15.4 | [{"value": 15.0, "product": "BrC1=CC2=C(N=C(S2)NC(=O)NCCCC(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.4, "product": "BrC1=CC2=C(N=C(S2)NC(=O)NCCCC(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 3 | HOUR | To a solution of ethyl 4-([(6-bromo-1,3-benzothiazol-2-yl)amino]carbonylamino)-butanoate (175 mg, 0.453 mmol) in THF/EtOH (1/1, 3 mL) was added 2 M NaOH (2.26 mL, 4.53 mmol). The reaction mixture was stirred at about 20° C. for about 3 hrs then 2 M HCl was added until pH<6 and a white precipitate was formed. The precip... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2scnc2c1 | Other | C1CCOC1.CCO | 20 | 3 | CCOC(=O)CCCNC(=O)Nc1nc2ccc(Br)cc2s1>C1CCOC1.CCO>O=C(O)CCCNC(=O)Nc1nc2ccc(Br)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a7c760657744469984c092df1b5dee3f | CCOC(=O)CCCNC(=O)Nc1nc2ccc(Br)cc2s1.CN1CCNCC1>>CN1CCN(C(=O)CCCNC(=O)Nc2nc3ccc(Br)cc3s2)CC1 | BrC1=CC2=C(N=C(S2)NC(=O)NCCCC(=O)OCC)C=C1.CN1CCNCC1>>BrC1=CC2=C(N=C(S2)NC(=O)NCCCC(=O)N2CCN(CC2)C)C=C1 | CCO[C:6](=[O:7])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:13])[NH:14][c:15]1[n:16][c:17]2[cH:18][cH:19][c:20]([Br:21])[cH:22][c:23]2[s:24]1.[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:25][CH2:26]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:13])[NH:14][c:15]2[n:16][c:17]3[cH:18][cH:19... | CCOC(=O)CCCNC(=O)Nc1nc2ccc(Br)cc2s1.CN1CCNCC1 | CN1CCN(C(=O)CCCNC(=O)Nc2nc3ccc(Br)cc3s2)CC1 | null | null | C1CCOC1 | Acylation | Aminolysis of esters | 44054b0a720986552e2e8320be5bb048d66cc126b8a9f454ed6799b617547a88 | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | O=C(NCCCC(=O)N1CCNCC1)Nc1nc2ccccc2s1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | 58.7 | [{"value": 53.0, "product": "BrC1=CC2=C(N=C(S2)NC(=O)NCCCC(=O)N2CCN(CC2)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.7, "product": "BrC1=CC2=C(N=C(S2)NC(=O)NCCCC(=O)N2CCN(CC2)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl 4-([(6-bromo-1,3-benzothiazol-2-yl)amino]carbonylamino)butanoate (100 mg, 0.259 mmol) was heated neat at about 80° C. in N-methyl-piperazine (259 mg, 2.59 mmol) for about 8 hrs. To the crude reaction mixture was added THF (2 mL), the ppt was filtered off and washed with THF (1 mL). The product was dried in vacuo ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2scnc2c1 | HO- | C1CCOC1 | null | null | CCOC(=O)CCCNC(=O)Nc1nc2ccc(Br)cc2s1.CN1CCNCC1>C1CCOC1>CN1CCN(C(=O)CCCNC(=O)Nc2nc3ccc(Br)cc3s2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c6be5838f30f427eb3af2ee3a70a8206 | CCNC(=O)Nc1nc2ccc(Br)cc2s1.OB(O)c1ccc(Cl)s1>>CCNC(=O)Nc1nc2ccc(-c3ccc(Cl)s3)cc2s1 | C([O-])([O-])=O.[Na+].[Na+].BrC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.COCCOC.ClC1=CC=C(S1)B(O)O>>ClC1=CC=C(S1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | Br[c:12]1[cH:11][cH:10][c:9]2[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:21][c:20]2[cH:19]1.OB(O)[c:13]1[cH:14][cH:15][c:16]([Cl:17])[s:18]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([Cl:17])[s:18]3)[cH:19][c:20]2[s:21]1 | CCNC(=O)Nc1nc2ccc(Br)cc2s1.OB(O)c1ccc(Cl)s1 | CCNC(=O)Nc1nc2ccc(-c3ccc(Cl)s3)cc2s1 | 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 | O | C-C Coupling | Suzuki coupling with boronic acids | 073b119126bd78a6aff4d8fd4da740f9dd6c6aad80d7cfe9f84366bdff0c4f84 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1csc(-c2ccc3ncsc3c2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1.O-B(-O)-[c;H0;D3;+0:10]1:[#16;a:11]:[c:12]:[c:13]:[c:14]:1>>[#16;a:11]1:[c:12]:[c:13]:[c:14]:[c;H0;D3;+0:10]:1-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1 | 16 | [{"value": 16.0, "product": "ClC1=CC=C(S1)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A 40 ml pressure tube was charged with about 100 mg N-(6-bromo-1,3-benzothiazol-2-yl)-N′-ethylurea, and about 2 ml ethylene glycol dimethyl ether. The slurry was stirred via magnetic stirbar followed by evacuation then release to nitrogen atmosphere (3 times). Next about 6 mol percent Pd(PPh3)4 was added, followed by a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2scnc2c1.c1ccsc1 | c1ccc2scnc2c1.c1ccsc1 | c1ccc2scnc2c1.c1ccsc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O | null | null | CCNC(=O)Nc1nc2ccc(Br)cc2s1.OB(O)c1ccc(Cl)s1>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.O>CCNC(=O)Nc1nc2ccc(-c3ccc(Cl)s3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-da8f787d822a47399faaf36eecd64351 | CCNC(=O)Nc1nc2ccc([N+](=O)[O-])cc2s1>>CCNC(=O)Nc1nc2ccc(-n3cccc3)cc2s1 | C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-]>>C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)N2C=CC=C2 | O=[N+:13]([O-])[c:12]1[cH:11][cH:10][c:9]2[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:20][c:19]2[cH:18]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12](-[n:13]3[cH:14][cH:15][cH:16][cH:17]3)[cH:18][c:19]2[s:20]1 | CCNC(=O)Nc1nc2ccc([N+](=O)[O-])cc2s1 | CCNC(=O)Nc1nc2ccc(-n3cccc3)cc2s1 | null | [Pt]=O | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 383fb3146c454a2e69adea831fdd6fe449f4652bf3b19b328514072b2babb695 | 899ebca2d6bba86d6be0360dea40833668d6eca1204c0c9fa1f9358f23c9856e | c1ccn(-c2ccc3ncsc3c2)c1 | O=[N+;H0;D3:1](-[O-])-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#16;a:8]:[c:9]:2:[c:10]:1>>[#16;a:8]1:[c:7]:[#7;a:6]:[c:5]2:[c:4]:[c:3]:[c;H0;D3;+0:2](-[n;H0;D3;+0:1]3:[c:11]:[c:12]:[c:13]:[c:14]:3):[c:10]:[c:9]:1:2 | null | [] | null | null | null | null | Charged about 500 mg N-ethyl-N′-(6-nitro-1,3-benzothiazol-2-yl)urea into about 75 ml ethanol. Added about 20 mg platinum oxide then evacuated and released to hydrogen three times. The system was then put under hydrogen pressure (about 20–40 psi) for about 5–20 hours. The reaction was stopped and the entire mass was fil... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | null | null | c1cc[nH]c1 | c1ccc2scnc2c1.c1cc[nH]c1 | null | [Pt]=O.C(C)O | null | null | CCNC(=O)Nc1nc2ccc([N+](=O)[O-])cc2s1>[Pt]=O.C(C)O>CCNC(=O)Nc1nc2ccc(-n3cccc3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d0a3bdf85e9b4840981acc50d0208080 | N#C[S-].N#Cc1ccc(N)cc1>>N#CCc1ccc2nc(N)sc2c1 | C(C1=CC=CC=C1)#N.[S-]C#N.[K+].NC1=CC=C(C#N)C=C1.BrBr>>NC=1SC2=C(N1)C=CC(=C2)CC#N | [C:9](#[N:10])[S-:11].[N:1]#[C:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:12][cH:13]1>>[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([NH2:10])[s:11][c:12]2[cH:13]1 | N#C[S-].N#Cc1ccc(N)cc1 | N#CCc1ccc2nc(N)sc2c1 | null | null | O.C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 397b96650975bf34f17e05ddbe438fef6e1fd7103ea65d5ad8b7aa4a37452d94 | 394ea87b83c9c542ea4eea948078b5a3b0234da2b1b0b3ed3a7f4d7a9ececa89 | c1ccc2scnc2c1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[S-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c:6]1:[c:7]:[cH;D2;+0:8]:[c:9](-[NH2;D1;+0:10]):[c:11]:[c:12]:1>>[N;H0;D1;+0:4]#[C:13]-[CH2;D2;+0:5]-[c:6]1:[c:7]:[c;H0;D3;+0:8]2:[s;H0;D2;+0:3]:[c;H0;D3;+0:2](-[NH2;D1;+0:1]):[n;H0;D2;+0:10]:[c:9]:2:[c:11]:[c:12]:1 | null | [] | 16 | CELSIUS | 16 | HOUR | 2 grams of 4-aminobenzonitrile is dissolved in about 40 mL acetic acid and the solution is cooled to about 16° C. About 3.3 g of potassium thiocyanate is added and the flask is equipped with an addition funnel. The addition funnel is charged with about 2.7 g bromine and about 5 ml acetic acid. This dark solution is the... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Nitrile.Primary amine | Nitrile.Primary amine | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | null | O.C(C)(=O)O | 16 | 16 | N#C[S-].N#Cc1ccc(N)cc1>O.C(C)(=O)O>N#CCc1ccc2nc(N)sc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5781a6f057c43938316f29e4db42aaf | CCN=C=O.N#Cc1ccc2nc(N)sc2c1>>CCNC(=O)Nc1nc2ccc(C#N)cc2s1 | NC=1SC2=C(N1)C=CC(=C2)C#N.C(C)N=C=O.C(C)N(CC)CC>>C(#N)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][c:16]2[s:17]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][c:16]2[s:17]1 | CCN=C=O.N#Cc1ccc2nc(N)sc2c1 | CCNC(=O)Nc1nc2ccc(C#N)cc2s1 | null | null | CN(C=O)C | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc2scnc2c1 | [C;D1;H3:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[C;D1;H3:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1 | null | [] | 80 | CELSIUS | 4 | HOUR | 0.2 grams of 2-amino-1,3-benzothiazole-6-carbonitrile is dissolved in about 5 ml dimethylformamide. About 0.2 ml of ethylisocyanate is added followed by about 0.3 ml triethylamine and the solution is heated to about 80° C. under good agitation. The solution is allowed to stir for about 4 hours then cooled to RT. The so... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2scnc2c1 | null | CN(C=O)C | 80 | 4 | CCN=C=O.N#Cc1ccc2nc(N)sc2c1>CN(C=O)C>CCNC(=O)Nc1nc2ccc(C#N)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-169aea1b049e4e39bff2a3959b722b9c | CCN1CN(C)CN(c2nc3ccc([N+](=O)[O-])c(CC#N)c3s2)C1=O>>CCN1CN(C)CN(c2nc3ccc4noc(C#N)c4c3s2)C1=O | C(C)N1C(N(CN(C1)C)C=1SC2=C(N1)C=CC(=C2CC#N)[N+](=O)[O-])=O.C(C)N(CC)CC.C[Si](C)(C)Cl>>C(C)N1C(N(CN(C1)C)C=1SC2=C(C=CC3=NOC(=C32)C#N)N1)=O | O=[N+:15]([c:14]1[cH:13][cH:12][c:11]2[n:10][c:9]([N:8]3[CH2:7][N:5]([CH3:6])[CH2:4][N:3]([CH2:2][CH3:1])[C:23]3=[O:24])[s:22][c:21]2[c:20]1[CH2:17][C:18]#[N:19])[O-:16]>>[CH3:1][CH2:2][N:3]1[CH2:4][N:5]([CH3:6])[CH2:7][N:8]([c:9]2[n:10][c:11]3[cH:12][cH:13][c:14]4[n:15][o:16][c:17]([C:18]#[N:19])[c:20]4[c:21]3[s:22]2)... | CCN1CN(C)CN(c2nc3ccc([N+](=O)[O-])c(CC#N)c3s2)C1=O | CCN1CN(C)CN(c2nc3ccc4noc(C#N)c4c3s2)C1=O | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 713cf10915426f5bdabff81cb22e1babf5494dc2aff023d41b0b0df6471156be | 899ebca2d6bba86d6be0360dea40833668d6eca1204c0c9fa1f9358f23c9856e | O=C1NCNCN1c1nc2ccc3nocc3c2s1 | O=[N+;H0;D3:1](-[O-;H0;D1:2])-[c:3](:[c:4]):[c:5](-[CH2;D2;+0:6]-[C:7]#[N;D1;H0:8]):[c:9]1:[#16;a:10]:[c:11]:[#7;a:12]:[c:13]:1>>[N;D1;H0:8]#[C:7]-[c;H0;D3;+0:6]1:[o;H0;D2;+0:2]:[n;H0;D2;+0:1]:[c:3](:[c:4]):[c:5]:1:[c:9]1:[#16;a:10]:[c:11]:[#7;a:12]:[c:13]:1 | null | [] | null | null | null | null | 0.2 g of [2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-6-nitro-1,3-benzothiazol-7-yl]methyl cyanide was charged into about 2 ml dimethylformamide. About 15 equivalents of triethylamine were then added followed by about 15 equivalents of trimethylsilyl chloride. The solution was stirred at room temperature for about ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | null | c1ccc2scnc2c1 | c1nc2ccc3nocc3c2s1 | C1[NH]C[NH]C[NH]1.c1nc2ccc3nocc3c2s1 | HO- | CN(C=O)C | null | null | CCN1CN(C)CN(c2nc3ccc([N+](=O)[O-])c(CC#N)c3s2)C1=O>CN(C=O)C>CCN1CN(C)CN(c2nc3ccc4noc(C#N)c4c3s2)C1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-34249f7514334ca392c080e846c96fb6 | CCNC(=O)Nc1nc2ccc(C#N)cc2s1.[OH-]>>CCNC(=O)Nc1nc2ccc(C(=O)O)cc2s1 | C(#N)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.[OH-].[K+].O1CCOCC1>>C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)C(=O)O | N#[C:13][c:12]1[cH:11][cH:10][c:9]2[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:18][c:17]2[cH:16]1.[OH-:14]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[OH:15])[cH:16][c:17]2[s:18]1 | CCNC(=O)Nc1nc2ccc(C#N)cc2s1.[OH-] | CCNC(=O)Nc1nc2ccc(C(=O)O)cc2s1 | null | null | null | Acylation | OtherReaction | e05c34ebe51fe654c61f91bb118ee544dcd0a035df9f073c07f2e1b77a1f299a | e722778fc7d66899e0f2f256942c8c213a77617f32bb1410d97747833c62e260 | c1ccc2scnc2c1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6].[OH-;D0:7]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](-[O;D1;H1:8])=[O;H0;D1;+0:7]):[c:3] | null | [] | null | null | null | null | About 60 mg N-(6-cyano-1,3-benzothiazol-2-yl)-N′-ethylurea was charged into about 5 mL of about a 1:1 mixture of about 2N aq KOH and dioxane. The reaction mixture was then brought to reflux for about 12–24 hours. Upon cooling, the reaction mixture was poured into about 25 mL of dilute aqueous acid. The white precipitat... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Carboxylic acid | null | null | c1ccc2scnc2c1 | null | null | null | null | CCNC(=O)Nc1nc2ccc(C#N)cc2s1.[OH-]>>CCNC(=O)Nc1nc2ccc(C(=O)O)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c31608d9ad04d16b80f61e52ee18c38 | CCN=C=O.Nc1nc2ccc(Br)cc2s1>>CCNC(=O)Nc1nc2ccc(Br)cc2s1 | BrC1=CC2=C(N=C(S2)N)C=C1.C(C)N=C=O.C(C)N(CC)CC>>BrC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]2[s:16]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][c:15]2[s:16]1 | CCN=C=O.Nc1nc2ccc(Br)cc2s1 | CCNC(=O)Nc1nc2ccc(Br)cc2s1 | null | null | CN(C)C=O | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc2scnc2c1 | [C;D1;H3:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[C;D1;H3:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1 | null | [] | 80 | CELSIUS | 4 | HOUR | About 0.75 g of 6-bromo-1,3-benzothiazol-2-amine (crude) is dissolved in about 15 mL DMF. About 0.5 mL of ethylisocyanate is added followed by about 0.9 mL triethylamine and the solution is heated to about 80° C. under good agitation. The solution is allowed to stir for about 4 hours then cooled to RT. The solvent is r... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2scnc2c1 | null | CN(C)C=O | 80 | 4 | CCN=C=O.Nc1nc2ccc(Br)cc2s1>CN(C)C=O>CCNC(=O)Nc1nc2ccc(Br)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-42e183c75b274ca58d1e4a2d590f020c | CCNC(=O)Nc1nc2ccc(C#N)cc2s1>>CCNC(=O)Nc1nc2ccc(C(N)=O)cc2s1 | C(#N)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.Cl.NO.C([O-])([O-])=O.[Na+].[Na+]>>C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)C(=O)N | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:16][c:17]2[s:18]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13]([NH2:14])=[O:15])[cH:16][c:17]2[s:18]1 | CCNC(=O)Nc1nc2ccc(C#N)cc2s1 | CCNC(=O)Nc1nc2ccc(C(N)=O)cc2s1 | null | null | null | Functional Group Addition | Nitrile to amide | 538c271df55faf6c40eed3b4a4f85f3f4e5c19a479326ea2f666ed82bd9b2b69 | 276fda5d5f5a53d66ac109e4f504751b1c2e3eef2b30a60eb746c3377c075030 | c1ccc2scnc2c1 | [#16;a:1]:[c:2]:[c:3]:[c:4](-[C;H0;D2;+0:5]#[N;H0;D1;+0:6]):[c:7]>>[#16;a:1]:[c:2]:[c:3]:[c:4](-[C;H0;D3;+0:5](-[NH2;D1;+0:6])=[O;D1;H0:8]):[c:7] | null | [] | null | null | null | null | About 1 g of N-(6-cyano-1,3-benzothiazol-2-yl)-N′-ethylurea was charged into about 30 mL of aqueous alkanol. Added about 0.6 g hydroxylamine hydrochloride and about 0.45 g sodium carbonate then heated to reflux. The solution was refluxed for about 4–8 hours then cooled to room temperature. The precipitate was recovered... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | c1ccc2scnc2c1 | Other | null | null | null | CCNC(=O)Nc1nc2ccc(C#N)cc2s1>>CCNC(=O)Nc1nc2ccc(C(N)=O)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e7c3ed99e5624aeda2d8f375a0cf6650 | CC(=O)O.CCNC(=O)Nc1nc2ccc(C(N)=NO)cc2s1>>CCNC(=O)Nc1nc2ccc(-c3noc(C)n3)cc2s1 | C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)C(N)=NO.C(C)(=O)O>>C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)C2=NOC(=N2)C | O=[C:16](O)[CH3:17].[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[N:14][OH:15])[NH2:18])[cH:19][c:20]2[s:21]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[n:14][o:15][c:16]([CH3:17])[n:18]3)[cH:19][c:20]2[s:21]1 | CC(=O)O.CCNC(=O)Nc1nc2ccc(C(N)=NO)cc2s1 | CCNC(=O)Nc1nc2ccc(-c3noc(C)n3)cc2s1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | a2ae31d0a4419b2c5154a805176ea647c4ecfa171a098253676fdd25dd7bb0eb | 125aa09f13da5a63d8a4326b5eb28b82ab752c0f025e52bd5183605dc71565a2 | c1nc(-c2ccc3ncsc3c2)no1 | O-[C;H0;D3;+0:1](=O)-[C;D1;H3:2].[NH2;D1;+0:3]-[C;H0;D3;+0:4](=[N;H0;D2;+0:5]-[OH;D1;+0:6])-[c;H0;D3;+0:7]1:[c:8]:[c:9]:[c:10]2:[#7;a:11]:[c:12]:[#16;a:13]:[c:14]:2:[c:15]:1>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:3]:[c;H0;D3;+0:4](-[c;H0;D3;+0:7]2:[c:8]:[c:9]:[c:10]3:[#7;a:11]:[c:12]:[#16;a:13]:[c:14]:3:[c:15]:2):[n;... | null | [] | 110 | CELSIUS | null | null | About 50 mg of 2-[(ethylamino)Carbonyl]amino-1,3-benzothiazole-6-carboxamideoxime was charged into about 1 mL of glacial acetic acid. The mixture was heated to about 110° C. then stirred at this temperature for about 12–20 hours. The solution was cooled to room temperature and the solvent was removed under reduced pres... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Oxime | null | null | c1ncon1 | c1ccc2scnc2c1.c1ncon1 | HO- | null | 110 | null | CC(=O)O.CCNC(=O)Nc1nc2ccc(C(N)=NO)cc2s1>>CCNC(=O)Nc1nc2ccc(-c3noc(C)n3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-032960dec0b94b21ba18a8f769a61520 | CCNC(=O)Nc1nc2ccc(C#N)cc2s1>>CCNC(=O)Nc1nc2ccc(CN)cc2s1 | C(#N)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>NCC1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:15][c:16]2[s:17]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([CH2:13][NH2:14])[cH:15][c:16]2[s:17]1 | CCNC(=O)Nc1nc2ccc(C#N)cc2s1 | CCNC(=O)Nc1nc2ccc(CN)cc2s1 | null | null | COCCOC | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc2scnc2c1 | [#16;a:1]:[c:2]:[c:3]:[c:4](-[C;H0;D2;+0:5]#[N;H0;D1;+0:6]):[c:7]>>[#16;a:1]:[c:2]:[c:3]:[c:4](-[CH2;D2;+0:5]-[NH2;D1;+0:6]):[c:7] | null | [] | null | null | null | null | About 0.05 g of N-(6-cyano-1,3-benzothiazol-2-yl)-N′-ethylurea was charged into about 10 mL of ethyleneglycol dimethylether. Introduced about 50 mg lithium aluminum hydride in several portions over about 12–24 hours. The slurry was quenched with about 5–10 mL ethyl acetate then about 1–2 mL of saturated aqueous sodium ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccc2scnc2c1 | null | COCCOC | null | null | CCNC(=O)Nc1nc2ccc(C#N)cc2s1>COCCOC>CCNC(=O)Nc1nc2ccc(CN)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1c22368b0e704f58812f062c12896e4b | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[N]=[N+]=[N-].CCNC(=O)Nc1nc2ccc(C#N)cc2s1>>CCNC(=O)Nc1nc2ccc(-c3nn[nH]n3)cc2s1 | C(#N)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1.N(=[N+]=[N-])[Sn](CCCC)(CCCC)CCCC>>C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)C=2N=NNN2 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[N:17]=[N+:15]=[N-:16].[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13]#[N:14])[cH:18][c:19]2[s:20]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[n:14][n:15][nH:16][n:17]3)[cH:18][c:19]2[s:20]1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[N]=[N+]=[N-].CCNC(=O)Nc1nc2ccc(C#N)cc2s1 | CCNC(=O)Nc1nc2ccc(-c3nn[nH]n3)cc2s1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | d793d4dee9d5a39dbd122d04a35a5f691674657d5f6e422ae31ce158ea438a57 | 95e338ac8e3158e8ab88ebe03ba7338cec0c32ed80de2cb9f73834a6f54aede3 | c1nc2ccc(-c3nn[nH]n3)cc2s1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[N;H0;D2;+0:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]2:[#7;a:10]:[c:11]:[#16;a:12]:[c:13]:2:[c:14]:1>>[#16;a:12]1:[c:11]:[#7;a:10]:[c:9]2:[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:5]3:[n;H0;D2;+0:4]:[n;H0;D2;+0:2]:[nH;D2;+0:3]... | null | [] | null | null | 30 | MINUTE | About 30 mg N-(6-cyano-1,3-benzothiazol-2-yl)-N′-ethylurea was charged into about 5 mL dry tetrahydrofuran. Added about 2 g of azidotributylstannane then refluxed for about 48–72 hours. The solvent was removed under reduced pressure then the crude oil was taken up in dichloromethane. About 0.5 mL of dilute aqueous hydr... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Nitrile.Tin | null | null | c1nnn[nH]1 | c1ccc2scnc2c1.c1nnn[nH]1 | Sn | O1CCCC1 | null | 0.5 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[N]=[N+]=[N-].CCNC(=O)Nc1nc2ccc(C#N)cc2s1>O1CCCC1>CCNC(=O)Nc1nc2ccc(-c3nn[nH]n3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7e0ae6c8d873495eb76902d9b21f0789 | CCN(CC)CC.CCN=C=NCCCN(C)C.CCNC(=O)Nc1nc2ccc(C(=O)O)cc2s1>>CCNC(=O)Nc1nc2ccc(C(=O)Nc3ccccc3)cc2s1 | Cl.C(C)N=C=NCCCN(C)C.C(C)NC(=O)NC=1SC2=C(N1)C=CC(=C2)C(=O)O.ClCCl.C(C)N(CC)CC>>C1(=CC=CC=C1)NC(=O)C1=CC2=C(N=C(S2)NC(=O)NCC)C=C1 | CCN(CC)[CH2:21][CH3:20].CN(C)C[CH2:19][CH2:18][N:15]=[C:16]=NC[CH3:17].O[C:13]([c:12]1[cH:11][cH:10][c:9]2[n:8][c:7]([NH:6][C:4]([NH:3][CH2:2][CH3:1])=[O:5])[s:24][c:23]2[cH:22]1)=[O:14]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[NH:15][c:16]3[cH:17][cH:18][cH:19][cH:2... | CCN(CC)CC.CCN=C=NCCCN(C)C.CCNC(=O)Nc1nc2ccc(C(=O)O)cc2s1 | CCNC(=O)Nc1nc2ccc(C(=O)Nc3ccccc3)cc2s1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ba6e95c4a5cac3abe5f8e61b2e9419dcca18b1f02d6ce345578d574e79b7e116 | 29bbbe02bc63f1a9bd090f686f9a3f9cb37bf2e7663e5d402874224454dc4e5c | O=C(Nc1ccccc1)c1ccc2ncsc2c1 | C-C-N(-C-C)-[CH2;D2;+0:1]-[CH3;D1;+0:2].C-N(-C)-C-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=N-C-[CH3;D1;+0:7].O-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c:10](:[c:11]):[c:12]:[c:13]:[#16;a:14]>>[#16;a:14]:[c:13]:[c:12]:[c:10](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[NH;D2;+0:5]-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[cH;D2;+0:4]:[cH;... | null | [] | null | null | null | null | About 0.2 g of 2-[(ethylamino)Carbonyl]amino-1,3-benzothiazole-6-carboxylic acid was dissolved into about 20 mL dichloromethane and about 0.2 mL triethylamine. Added about 1 eq of the appropriate amine followed by about 0.3 g of 1-ethyl-3-(3-dimethylaminopropyl)Carbodiimide hydrochloride then stirred at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amine.Tertiary amine | Secondary amide | null | c1ccccc1 | c1ccc2scnc2c1.c1ccccc1 | HO- | null | null | null | CCN(CC)CC.CCN=C=NCCCN(C)C.CCNC(=O)Nc1nc2ccc(C(=O)O)cc2s1>>CCNC(=O)Nc1nc2ccc(C(=O)Nc3ccccc3)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-157697f4a0e64340ac2d0e8d298b748a | CCN=C=O.N#CCc1ccc2nc(N)sc2c1>>CCNC(=O)Nc1nc2c(C#N)cc(C)cc2s1 | NC=1SC2=C(N1)C=CC(=C2)CC#N.C(C)N=C=O.C(C)N(CC)CC>>CC1=CC2=C(N=C(S2)NC(=O)NCC)C(=C1)C#N | [CH3:1][CH2:2][N:3]=[C:4]=[O:5].[NH2:6][c:7]1[n:8][c:9]2[cH:10][cH:13][c:14]([CH2:15][C:11]#[N:12])[cH:16][c:17]2[s:18]1>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[NH:6][c:7]1[n:8][c:9]2[c:10]([C:11]#[N:12])[cH:13][c:14]([CH3:15])[cH:16][c:17]2[s:18]1 | CCN=C=O.N#CCc1ccc2nc(N)sc2c1 | CCNC(=O)Nc1nc2c(C#N)cc(C)cc2s1 | null | null | CN(C=O)C | Acylation | OtherReaction | a555219857081d2ad7ef81ec69c218343654c5e77a343c85dbef6615c1f0d2c0 | f69bb2bb9d516dbd81508bf932ee71e4b87e59824894c0de2300897f5b49b745 | c1ccc2scnc2c1 | [C;D1;H3:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[N;D1;H0:6]#[C;H0;D2;+0:7]-[CH2;D2;+0:8]-[c:9]1:[c:10]:[cH;D2;+0:11]:[c:12]2:[#7;a:13]:[c:14](-[NH2;D1;+0:15]):[#16;a:16]:[c:17]:2:[c:18]:1>>[C;D1;H3:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:15]-[c:14]1:[#16;a:16]:[c:17]2:[c:18]:[c:9](-[CH3... | null | [] | 80 | CELSIUS | null | null | About 1 g of (2-amino-1,3-benzothiazol-6-yl)methyl cyanide is dissolved in about 10 ml dimethylformamide. About 0.8 ml of ethylisocyanate is added followed by about 1.4 ml triethylamine and the solution is heated to about 80° C. under good agitation. The solution is allowed to stir for about 4–6 hours then cooled to RT... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Isocyanate.Primary amine | Urea.Nitrile | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | null | CN(C=O)C | 80 | null | CCN=C=O.N#CCc1ccc2nc(N)sc2c1>CN(C=O)C>CCNC(=O)Nc1nc2c(C#N)cc(C)cc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-59f92c1ad5ac44d88c3cda7c11cfe96d | Brc1ccccn1.C#CCC>>CCC#Cc1ccccn1 | BrC1=NC=CC=C1.C#CCC>>C(#CCC)C1=NC=CC=C1 | Br[c:5]1[cH:6][cH:7][cH:8][cH:9][n:10]1.[CH3:1][CH2:2][C:3]#[CH:4]>>[CH3:1][CH2:2][C:3]#[C:4][c:5]1[cH:6][cH:7][cH:8][cH:9][n:10]1 | Brc1ccccn1.C#CCC | CCC#Cc1ccccn1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I | C(C)NCC | C-C Coupling | Sonogashira alkyne_aryl halide | d920908f7cd8d5c12cc1e0ae172ea45585ee68f03cd2df6faa8b9163bac60cda | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccncc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]#[CH;D1;+0:8]>>[C:6]-[C:7]#[C;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 84.3 | [{"value": 84.3, "product": "C(#CCC)C1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | After dissolving 2-bromopyridine (50 g) in diethylamine (500 mL) and adding dichlorobis(triphenylphosphine)palladium (II) (2.2 g) and copper iodide (0.3 g), the mixture was stirred at room temperature for 4 hours while introducing 1-butyne (100 g) as a gas. After bubbling in nitrogen, extraction was performed with ethy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I.C(C)NCC | null | 4 | Brc1ccccn1.C#CCC>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I.C(C)NCC>CCC#Cc1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a32947a36a4c48d3857c5a4f444f36ff | CCC#Cc1ccccn1.Cc1cc(C)c(S(=O)(=O)ON)c(C)c1>>CCC#Cc1cccc[n+]1N.Cc1cc(C)c(S(=O)(=O)[O-])c(C)c1 | C(#CCC)C1=NC=CC=C1.C1(=C(C(=CC(=C1)C)C)S(=O)(=O)ON)C.C(C)OCC>>C1(=C(C(=CC(=C1)C)C)S(=O)(=O)[O-])C.N[N+]1=C(C=CC=C1)C#CCC | [CH3:1][CH2:2][C:3]#[C:4][c:5]1[cH:6][cH:7][cH:8][cH:9][n:10]1.[NH2:11][O:21][S:18]([c:17]1[c:15]([CH3:16])[cH:14][c:13]([CH3:12])[cH:24][c:22]1[CH3:23])(=[O:19])=[O:20]>>[CH3:1][CH2:2][C:3]#[C:4][c:5]1[cH:6][cH:7][cH:8][cH:9][n+:10]1[NH2:11].[CH3:12][c:13]1[cH:14][c:15]([CH3:16])[c:17]([S:18](=[O:19])(=[O:20])[O-:21])... | CCC#Cc1ccccn1.Cc1cc(C)c(S(=O)(=O)ON)c(C)c1 | CCC#Cc1cccc[n+]1N.Cc1cc(C)c(S(=O)(=O)[O-])c(C)c1 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | cfb63745f189977587aa9e27a48e3c94bc67f3cedb55b082d16d68a474a5dc03 | 0fa8940bc5d0eb59a8f49f15dce42784db5d66cb6be3b4bd563c02ae729e2bb2 | c1cc[nH+]cc1.c1ccccc1 | [C;D1;H3:1]-[c:2]1:[c:3]:[c:4](-[C;D1;H3:5]):[c:6](-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[O;H0;D2;+0:10]-[NH2;D1;+0:11]):[c:12](-[C;D1;H3:13]):[c:14]:1.[C:15]-[C:16]#[C:17]-[c:18](:[c:19]):[n;H0;D2;+0:20]:[c:21]:[c:22]>>[C;D1;H3:1]-[c:2]1:[c:3]:[c:4](-[C;D1;H3:5]):[c:6](-[#16:7](-[O-;H0;D1:10])(=[O;D1;H0:8])=[O;D1;H0:9]... | 39.1 | [{"value": 39.1, "product": "C1(=C(C(=CC(=C1)C)C)S(=O)(=O)[O-])C.N[N+]1=C(C=CC=C1)C#CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | After dissolving 2-(1-butynyl)pyridine (12.8 g) in dichloromethane (60 mL), a solution of O-mesitylenesulfonylhydroxyamine (Reference document: Synthesis, 1997, 1) (20 g) in dichloromethane (132 mL) was added dropwise while cooling on ice, and the mixture was stirred for 30 minutes. Diethyl ether (2 L) was added to the... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Primary amine | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.c1ccccc1 | null | ClCCl | null | 0.5 | CCC#Cc1ccccn1.Cc1cc(C)c(S(=O)(=O)ON)c(C)c1>ClCCl>CCC#Cc1cccc[n+]1N.Cc1cc(C)c(S(=O)(=O)[O-])c(C)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e2417cce65cb4c1590485a0406f53f9b | CCC#Cc1cccc[n+]1N>>CCc1cc2ccccn2n1 | C1(=C(C(=CC(=C1)C)C)S(=O)(=O)[O-])C.N[N+]1=C(C=CC=C1)C#CCC.CC(C)([O-])C.[K+]>>C(C)C1=NN2C(C=CC=C2)=C1 | [CH3:1][CH2:2][C:3]#[C:4][c:5]1[cH:6][cH:7][cH:8][cH:9][n+:10]1[NH2:11]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][n:10]2[n:11]1 | CCC#Cc1cccc[n+]1N | CCc1cc2ccccn2n1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 76961428dc19075c072c6c5a3ec5b4a1395fb776af9a698445dd989c38b1f419 | f32b9a5ecc70d866a53cd56f9bc47b365771cdcbb02563cae8c78e4de228d870 | c1ccn2nccc2c1 | [C;D1;H3:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[c:5](:[c:6]):[n+;H0;D3:7](-[NH2;D1;+0:8]):[c:9]:[c:10]>>[C;D1;H3:1]-[C:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c:5](:[c:6]):[n;H0;D3;+0:7](:[c:9]:[c:10]):[n;H0;D2;+0:8]:1 | null | [] | null | null | 30 | MINUTE | A 6.1 g portion of the obtained N-amino-2-(1-butynyl)pyridinium mesitylenesulfonate was dissolved in tetrahydrofuran (600 mL), potassium tert-butoxide (3.55 g) was added at room temperature, and the mixture was vigorously stirred for 30 minutes. After adding ice water to the reaction mixture, extraction was performed w... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Alkyne | null | C1=CC=[NH+]C=C1 | c1ccn2nccc2c1 | c1ccn2nccc2c1 | null | O1CCCC1 | null | 0.5 | CCC#Cc1cccc[n+]1N>O1CCCC1>CCc1cc2ccccn2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2d57ba5cdf1547dca6908aa7dd81c8e7 | CCc1cc2ccccn2n1.ClC(Cl)(Br)C(Cl)(Cl)Br>>CCc1cc2cccc(Br)n2n1 | O.CCCCCC.C(CCC)[Li].C(C)C1=NN2C(C=CC=C2)=C1.BrC(C(Cl)(Cl)Br)(Cl)Cl>>BrC1=CC=CC=2N1N=C(C2)CC | [CH3:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][n:11]2[n:12]1.ClC(Cl)(Br)C(Cl)(Cl)[Br:10]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([Br:10])[n:11]2[n:12]1 | CCc1cc2ccccn2n1.ClC(Cl)(Br)C(Cl)(Cl)Br | CCc1cc2cccc(Br)n2n1 | null | null | O1CCCC1 | Functional Group Interconversion | Bromination | 239df31471b347eeb51abec73301027b6f1036c85391671e1491db98f67e85bb | 019ad5fd0dfe62cfb4244afde83961e2345586820445df7561489ed4a5d090fa | c1ccn2nccc2c1 | Br-C(-Cl)(-Cl)-C(-Cl)(-Cl)-[Br;H0;D1;+0:1].[c:2]:[#7;a:3]:[#7;a:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[#7;a:4](:[c:5]):[#7;a:3]:[c:2] | 73.1 | [{"value": 73.1, "product": "BrC1=CC=CC=2N1N=C(C2)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | After dissolving 2-ethylpyrazolo[1,5-a]pyridine (80 mg) in tetrahydrofuran (1 mL), an n-butyllithiumhexane solution (1.6 M; 0.58 mL) was added dropwise at −78° C. under a nitrogen stream, and the mixture was stirred for 30 minutes. A solution of 1,2-dibromo-1,1,2,2-tetrachloroethane (196 mg) in tetrahydrofuran (0.5 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide | Aromatic halide | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1ccn2nccc2c1 | HCl.Br- | O1CCCC1 | null | 0.5 | CCc1cc2ccccn2n1.ClC(Cl)(Br)C(Cl)(Cl)Br>O1CCCC1>CCc1cc2cccc(Br)n2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f014e611ef1f44afbd81fa386b31f468 | CCc1cc2cccc(Br)n2n1.OB(O)Oc1ccc(Cl)cc1Cl>>CCc1cc2cccc(-c3ccc(Cl)cc3Cl)n2n1 | BrC1=CC=CC=2N1N=C(C2)CC.ClC1=C(C=CC(=C1)Cl)OB(O)O.C([O-])([O-])=O.[Na+].[Na+].O>>ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2)CC | Br[c:9]1[cH:8][cH:7][cH:6][c:5]2[cH:4][c:3]([CH2:2][CH3:1])[n:19][n:18]21.OB(O)O[c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]1[Cl:17]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]3[Cl:17])[n:18]2[n:19]1 | CCc1cc2cccc(Br)n2n1.OB(O)Oc1ccc(Cl)cc1Cl | CCc1cc2cccc(-c3ccc(Cl)cc3Cl)n2n1 | 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 | C(C)(=O)OCC.C1(=CC=CC=C1)C.C(C)O | C-C Coupling | OtherReaction | 8b93332ffb86325cf5e747a3ea9faae13848b7451cf269888446bfaf73495994 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2cccc3ccnn23)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[#7;a:4](:[c:5]):[#7;a:6]:[c:7].O-B(-O)-O-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[Cl;D1;H0:12]):[c:13]>>[Cl;D1;H0:12]-[c:11](:[c:13]):[c;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[#7;a:4](:[c:5]):[#7;a:6]:[c:7]):[c:9]:[c:10] | 97.9 | [{"value": 97.9, "product": "ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 3 | HOUR | After dissolving 7-bromo-2-ethylpyrazolo[1,5-a]pyridine (300 mg) in ethanol (2 mL) and toluene (4 mL), 2,4-dichlorophenylboric acid (508 mg), tetrakis(triphenylphosphine)palladium (0) complex (154 mg) and 2 M aqueous sodium carbonate (1.33 mL) were added and the mixture was heated and stirred at 80° C. for 3 hours unde... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccn2nccc2c1.c1ccccc1 | c1ccn2nccc2c1.c1ccccc1 | c1ccn2nccc2c1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)(=O)OCC.C1(=CC=CC=C1)C.C(C)O | 80 | 3 | CCc1cc2cccc(Br)n2n1.OB(O)Oc1ccc(Cl)cc1Cl>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.C(C)(=O)OCC.C1(=CC=CC=C1)C.C(C)O>CCc1cc2cccc(-c3ccc(Cl)cc3Cl)n2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b0d69462f11d46589ba57d6318c7fae0 | CCc1cc2cccc(-c3ccc(Cl)cc3Cl)n2n1.O=[N+]=O>>CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1[N+](=O)[O-] | C(C)(=O)OCC.ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2)CC.F[B-](F)(F)F.O=[N+]=O>>ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2[N+](=O)[O-])CC | [CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]3[Cl:14])[cH:15][cH:16][cH:17][c:18]2[cH:19]1.[N+:20](=[O:21])=[O:22]>>[CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]3[Cl:14])[cH:15][cH:16][cH:17][c:18]2[c:19]1[N+:20](=[O:21])[O-:22] | CCc1cc2cccc(-c3ccc(Cl)cc3Cl)n2n1.O=[N+]=O | CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1[N+](=O)[O-] | null | null | C(C)#N | Functional Group Addition | OtherReaction | 65728576257e862e6f8831bda024c42d2bf3db26bad9969b734818bd376bd9c5 | 5c75a9bf759be9717d985245c85c84dbfff904ea5287869736b84fdaa57f1e27 | c1ccc(-c2cccc3ccnn23)cc1 | [C:1]-[c:2]1:[#7;a:3]:[#7;a:4](:[c:5]):[c:6](:[c:7]):[cH;D2;+0:8]:1.[O;D1;H0:9]=[N+;H0;D2:10]=[O;H0;D1;+0:11]>>[C:1]-[c:2]1:[#7;a:3]:[#7;a:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8]:1-[N+;H0;D3:10](-[O-;H0;D1:11])=[O;D1;H0:9] | 35.6 | [{"value": 35.6, "product": "ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2[N+](=O)[O-])CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | After dissolving 7-(2,4-dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridine (280 mg) in acetonitrile (20 mL), nitronium tetrafluoroborate (255 mg) was added 4 times at 30 minute intervals while stirring on ice. The reaction mixture was added to ice water, extraction was performed with ethyl acetate and the extract was washe... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso.Nitroso | Nitro group | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1ccccc1.c1ccn2nccc2c1 | null | C(C)#N | null | null | CCc1cc2cccc(-c3ccc(Cl)cc3Cl)n2n1.O=[N+]=O>C(C)#N>CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9dbfc3c4f4ce448e87c72ec2f1ff0d08 | CCc1cc2cccc(Br)n2n1.O=[N+]=O>>CCc1nn2c(Br)cccc2c1[N+](=O)[O-] | C(C)(=O)OCC.BrC1=CC=CC=2N1N=C(C2)CC.F[B-](F)(F)F.O=[N+]=O>>BrC1=CC=CC=2N1N=C(C2[N+](=O)[O-])CC | [CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6]([Br:7])[cH:8][cH:9][cH:10][c:11]2[cH:12]1.[N+:13](=[O:14])=[O:15]>>[CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6]([Br:7])[cH:8][cH:9][cH:10][c:11]2[c:12]1[N+:13](=[O:14])[O-:15] | CCc1cc2cccc(Br)n2n1.O=[N+]=O | CCc1nn2c(Br)cccc2c1[N+](=O)[O-] | null | null | C(C)#N | Functional Group Addition | OtherReaction | 65728576257e862e6f8831bda024c42d2bf3db26bad9969b734818bd376bd9c5 | 5c75a9bf759be9717d985245c85c84dbfff904ea5287869736b84fdaa57f1e27 | c1ccn2nccc2c1 | [C:1]-[c:2]1:[#7;a:3]:[#7;a:4](:[c:5]):[c:6](:[c:7]):[cH;D2;+0:8]:1.[O;D1;H0:9]=[N+;H0;D2:10]=[O;H0;D1;+0:11]>>[C:1]-[c:2]1:[#7;a:3]:[#7;a:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8]:1-[N+;H0;D3:10](-[O-;H0;D1:11])=[O;D1;H0:9] | 50.8 | [{"value": 50.8, "product": "BrC1=CC=CC=2N1N=C(C2[N+](=O)[O-])CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | After dissolving 7-bromo-2-ethylpyrazolo[1,5-a]pyridine (1.1 g) in acetonitrile (20 mL), nitronium tetrafluoroborate (1.3 g) was added while stirring on ice, and stirring was continued for 30 minutes. The reaction mixture was added to ice water, extraction was performed with ethyl acetate and the extract was washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso.Nitroso | Nitro group | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1ccn2nccc2c1 | null | C(C)#N | null | 0.5 | CCc1cc2cccc(Br)n2n1.O=[N+]=O>C(C)#N>CCc1nn2c(Br)cccc2c1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9528c738ae574cb594267acce885900b | CCc1nn2c(Br)cccc2c1[N+](=O)[O-].COc1ccc(OB(O)O)c(Cl)c1>>CCc1nn2c(-c3ccc(OC)cc3Cl)cccc2c1[N+](=O)[O-] | BrC1=CC=CC=2N1N=C(C2[N+](=O)[O-])CC.ClC1=C(C=CC(=C1)OC)OB(O)O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C(C)(=O)OCC>>ClC1=C(C=CC(=C1)OC)C1=CC=CC=2N1N=C(C2[N+](=O)[O-])CC | Br[c:6]1[n:5]2[n:4][c:3]([CH2:2][CH3:1])[c:20]([N+:21](=[O:22])[O-:23])[c:19]2[cH:18][cH:17][cH:16]1.OB(O)O[c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][c:14]1[Cl:15]>>[CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][c:14]3[Cl:15])[cH:16][cH:17][cH:18][c:19]2[c:20]1[N+:21](=[O:22]... | CCc1nn2c(Br)cccc2c1[N+](=O)[O-].COc1ccc(OB(O)O)c(Cl)c1 | CCc1nn2c(-c3ccc(OC)cc3Cl)cccc2c1[N+](=O)[O-] | 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 | O.COCCOC | C-C Coupling | OtherReaction | 8b93332ffb86325cf5e747a3ea9faae13848b7451cf269888446bfaf73495994 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2cccc3ccnn23)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[#7;a:4](:[c:5]):[#7;a:6]:[c:7].O-B(-O)-O-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[Cl;D1;H0:12]):[c:13]>>[Cl;D1;H0:12]-[c:11](:[c:13]):[c;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[#7;a:4](:[c:5]):[#7;a:6]:[c:7]):[c:9]:[c:10] | 73.3 | [{"value": 73.3, "product": "ClC1=C(C=CC(=C1)OC)C1=CC=CC=2N1N=C(C2[N+](=O)[O-])CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 3 | HOUR | After dissolving 7-bromo-2-ethyl-3-nitropyrazolo[1,5-a]pyridine (100 mg) in 1,2-dimethoxyethane (6 mL) and water (1 mL), 2-chloro-4-methoxyphenylboric acid (138 mg), tetrakis(triphenylphosphine)palladium (0) complex (86 mg) and barium hydroxide octahydrate (233 mg) were added and the mixture was heated and stirred at 8... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccn2nccc2c1.c1ccccc1 | c1ccccc1.c1ccn2nccc2c1 | c1ccccc1.c1ccn2nccc2c1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | 80 | 3 | CCc1nn2c(Br)cccc2c1[N+](=O)[O-].COc1ccc(OB(O)O)c(Cl)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>CCc1nn2c(-c3ccc(OC)cc3Cl)cccc2c1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c955a68fd91c4d9193e9298121138839 | C#CCC.COc1cccnc1Br>>CCC#Cc1cc(OC)ccn1 | BrC1=NC=CC=C1OC.C#CCC.C(C)NCC>>C(#CCC)C1=NC=CC(=C1)OC | [CH3:1][CH2:2][C:3]#[CH:4].Br[c:6]1[c:7]([O:8][CH3:9])[cH:10][cH:11][cH:5][n:12]1>>[CH3:1][CH2:2][C:3]#[C:4][c:5]1[cH:6][c:7]([O:8][CH3:9])[cH:10][cH:11][n:12]1 | C#CCC.COc1cccnc1Br | CCC#Cc1cc(OC)ccn1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I | null | C-C Coupling | OtherReaction | d920908f7cd8d5c12cc1e0ae172ea45585ee68f03cd2df6faa8b9163bac60cda | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccncc1 | Br-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[cH;D2;+0:3]:[cH;D2;+0:4]:[c:5]:[c:6]:1-[#8:7].[C:8]-[C:9]#[CH;D1;+0:10]>>[#8:7]-[c:6]1:[c:5]:[cH;D2;+0:4]:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C;H0;D2;+0:10]#[C:9]-[C:8]):[cH;D2;+0:1]:1 | null | [] | null | null | 20 | HOUR | After adding dichlorobis(triphenylphosphine)palladium (II) (671 mg) and copper iodide (91 mg) to a solution of 2-bromo-3-methoxypyridine (18.0 g) in diethylamine (250 mL), 1-butyne (15.5 g) was bubbled through at room temperature, and the mixture was stirred for 20 hours. Upon completion of the reaction, the solvent wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I | null | 20 | C#CCC.COc1cccnc1Br>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.[Cu](I)I>CCC#Cc1cc(OC)ccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0fbfc8c11b524a2cb943421f7379b2a2 | CCC#Cc1cc(OC)ccn1.Cc1cc(C)c(S(=O)(=O)ON)c(C)c1>>CCC#Cc1cc(OC)cc[n+]1N.Cc1cc(C)c(S(=O)(=O)[O-])c(C)c1 | C(C)OCC.C(#CCC)C1=NC=CC(=C1)OC.C1(=C(C(=CC(=C1)C)C)S(=O)(=O)ON)C>>C1(=C(C(=CC(=C1)C)C)S(=O)(=O)[O-])C.N[N+]1=C(C=C(C=C1)OC)C#CCC | [CH3:1][CH2:2][C:3]#[C:4][c:5]1[cH:6][c:7]([O:8][CH3:9])[cH:10][cH:11][n:12]1.[NH2:13][O:23][S:20]([c:19]1[c:17]([CH3:18])[cH:16][c:15]([CH3:14])[cH:26][c:24]1[CH3:25])(=[O:21])=[O:22]>>[CH3:1][CH2:2][C:3]#[C:4][c:5]1[cH:6][c:7]([O:8][CH3:9])[cH:10][cH:11][n+:12]1[NH2:13].[CH3:14][c:15]1[cH:16][c:17]([CH3:18])[c:19]([S... | CCC#Cc1cc(OC)ccn1.Cc1cc(C)c(S(=O)(=O)ON)c(C)c1 | CCC#Cc1cc(OC)cc[n+]1N.Cc1cc(C)c(S(=O)(=O)[O-])c(C)c1 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | cfb63745f189977587aa9e27a48e3c94bc67f3cedb55b082d16d68a474a5dc03 | 0fa8940bc5d0eb59a8f49f15dce42784db5d66cb6be3b4bd563c02ae729e2bb2 | c1cc[nH+]cc1.c1ccccc1 | [C;D1;H3:1]-[c:2]1:[c:3]:[c:4](-[C;D1;H3:5]):[c:6](-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[O;H0;D2;+0:10]-[NH2;D1;+0:11]):[c:12](-[C;D1;H3:13]):[c:14]:1.[C:15]-[C:16]#[C:17]-[c:18](:[c:19]):[n;H0;D2;+0:20]:[c:21]:[c:22]>>[C;D1;H3:1]-[c:2]1:[c:3]:[c:4](-[C;D1;H3:5]):[c:6](-[#16:7](-[O-;H0;D1:10])(=[O;D1;H0:8])=[O;D1;H0:9]... | null | [] | null | null | 1 | HOUR | To a solution of the obtained 2-(1-butynyl)-4-methoxypyridine (10.0 g) in dichloromethane (100 mL) there was added dropwise a solution of O-mesitylenesulfonylhydroxyamine (16.0 g) in dichloromethane (100 mL) at 0° C., and the mixture was stirred for 1 hour. Diethyl ether (250 mL) was added to the reaction mixture, and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Primary amine | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.c1ccccc1 | null | ClCCl | null | 1 | CCC#Cc1cc(OC)ccn1.Cc1cc(C)c(S(=O)(=O)ON)c(C)c1>ClCCl>CCC#Cc1cc(OC)cc[n+]1N.Cc1cc(C)c(S(=O)(=O)[O-])c(C)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e725fe37874e4314be98d52b6aead169 | CCC#Cc1cc(OC)cc[n+]1N>>CCc1cc2c(OC)cccn2n1 | C(C)(=O)OCC.CC(C)([O-])C.[K+].C1(=C(C(=CC(=C1)C)C)S(=O)(=O)[O-])C.N[N+]1=C(C=C(C=C1)OC)C#CCC.O>>C(C)C1=NN2C(C(=CC=C2)OC)=C1 | [CH3:1][CH2:2][C:3]#[C:4][c:11]1[cH:5][c:6]([O:7][CH3:8])[cH:9][cH:10][n+:12]1[NH2:13]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([O:7][CH3:8])[cH:9][cH:10][cH:11][n:12]2[n:13]1 | CCC#Cc1cc(OC)cc[n+]1N | CCc1cc2c(OC)cccn2n1 | null | null | CN(C=O)C.O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 76961428dc19075c072c6c5a3ec5b4a1395fb776af9a698445dd989c38b1f419 | f32b9a5ecc70d866a53cd56f9bc47b365771cdcbb02563cae8c78e4de228d870 | c1ccn2nccc2c1 | [#8:1]-[c:2]1:[c:3]:[cH;D2;+0:4]:[n+;H0;D3:5](-[NH2;D1;+0:6]):[c;H0;D3;+0:7](-[C;H0;D2;+0:8]#[C;H0;D2;+0:9]-[C:10]-[C;D1;H3:11]):[cH;D2;+0:12]:1>>[#8:1]-[c:2]1:[c:3]:[cH;D2;+0:4]:[cH;D2;+0:7]:[n;H0;D3;+0:5]2:[n;H0;D2;+0:6]:[c;H0;D3;+0:9](-[C:10]-[C;D1;H3:11]):[cH;D2;+0:8]:[c;H0;D3;+0:12]:1:2 | 66.5 | [{"value": 66.5, "product": "C(C)C1=NN2C(C(=CC=C2)OC)=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Potassium tert-butoxide (11.1 g) was added to a solution of N-amino-2-(1-butynyl)-4-methoxypyridinium mesitylenesulfonate (20.7 g) in tetrahydrofuran (300 mL) and N,N-dimethylformamide (15 mL), and the mixture was stirred at room temperature for 1 hour. Water was added while cooling on ice, extraction was performed wit... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Alkyne | null | C1=CC=[NH+]C=C1 | c1ccn2nccc2c1 | c1ccn2nccc2c1 | null | CN(C=O)C.O1CCCC1 | null | 1 | CCC#Cc1cc(OC)cc[n+]1N>CN(C=O)C.O1CCCC1>CCc1cc2c(OC)cccn2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b182e6e6acd04d0da1ff082f2af748a0 | BrCCBr.CCc1cc2c(OC)cccn2n1>>CCc1cc2c(OC)ccc(Br)n2n1 | [Cl-].[NH4+].C(CCC)[Li].C(C)C1=NN2C(C(=CC=C2)OC)=C1.BrCCBr>>BrC1=CC=C(C=2N1N=C(C2)CC)OC | BrCC[Br:12].[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([O:7][CH3:8])[cH:9][cH:10][cH:11][n:13]2[n:14]1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([O:7][CH3:8])[cH:9][cH:10][c:11]([Br:12])[n:13]2[n:14]1 | BrCCBr.CCc1cc2c(OC)cccn2n1 | CCc1cc2c(OC)ccc(Br)n2n1 | null | null | O1CCCC1 | Functional Group Interconversion | Bromination | 45f2a64fd76bc339669d027148c9d9ecf1f240b29ad0040207cebf4b091ffdba | a8fd90d9727001deb7b4d3f63c2c94d8100018754aab15c0aa879096d979fed2 | c1ccn2nccc2c1 | Br-C-C-[Br;H0;D1;+0:1].[c:2]:[#7;a:3]:[#7;a:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[#7;a:4](:[c:5]):[#7;a:3]:[c:2] | null | [] | -78 | CELSIUS | 1 | HOUR | n-Butyllithium (1.31 mL) was slowly added dropwise to a solution of 2-ethyl-4-methoxypyrazolo[1,5-a]pyridine (303 mg) in tetrahydrofuran (15 mL) at −78° C. After stirring the mixture at −78° C. for 1 hour, 1,2-dibromoethane (0.18 mL) was added and stirring was continued for 1 hour. Saturated aqueous ammonium chloride w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | Aromatic halide | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1ccn2nccc2c1 | HBr | O1CCCC1 | -78 | 1 | BrCCBr.CCc1cc2c(OC)cccn2n1>O1CCCC1>CCc1cc2c(OC)ccc(Br)n2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6d8efc54b4a14188bbf41ce10a29232f | CCc1cc2c(OC)ccc(Br)n2n1.O=[N+]=O>>CCc1nn2c(Br)ccc(OC)c2c1[N+](=O)[O-] | F[B-](F)(F)F.O=[N+]=O.BrC1=CC=C(C=2N1N=C(C2)CC)OC.O>>BrC1=CC=C(C=2N1N=C(C2[N+](=O)[O-])CC)OC | [CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6]([Br:7])[cH:8][cH:9][c:10]([O:11][CH3:12])[c:13]2[cH:14]1.[N+:15](=[O:16])=[O:17]>>[CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6]([Br:7])[cH:8][cH:9][c:10]([O:11][CH3:12])[c:13]2[c:14]1[N+:15](=[O:16])[O-:17] | CCc1cc2c(OC)ccc(Br)n2n1.O=[N+]=O | CCc1nn2c(Br)ccc(OC)c2c1[N+](=O)[O-] | null | null | C(C)#N | Functional Group Addition | OtherReaction | 65728576257e862e6f8831bda024c42d2bf3db26bad9969b734818bd376bd9c5 | 5c75a9bf759be9717d985245c85c84dbfff904ea5287869736b84fdaa57f1e27 | c1ccn2nccc2c1 | [C:1]-[c:2]1:[#7;a:3]:[#7;a:4](:[c:5]):[c:6](:[c:7]):[cH;D2;+0:8]:1.[O;D1;H0:9]=[N+;H0;D2:10]=[O;H0;D1;+0:11]>>[C:1]-[c:2]1:[#7;a:3]:[#7;a:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8]:1-[N+;H0;D3:10](-[O-;H0;D1:11])=[O;D1;H0:9] | 47.9 | [{"value": 47.9, "product": "BrC1=CC=C(C=2N1N=C(C2[N+](=O)[O-])CC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | After adding nitronium tetrafluoroborate (176 mg) to a solution of 7-bromo-2-ethyl-4-methoxypyrazolo[1,5-a]pyridine (282 mg) in acetonitrile (20 mL) at 0° C., the mixture was stirred for 20 minutes. Upon completion of the reaction, water was added, extraction was performed with ethyl acetate, the extract was washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso.Nitroso | Nitro group | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1ccn2nccc2c1 | null | C(C)#N | null | 0.333333 | CCc1cc2c(OC)ccc(Br)n2n1.O=[N+]=O>C(C)#N>CCc1nn2c(Br)ccc(OC)c2c1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b861c7d6b3d849a4a898b1f520c04f67 | CCc1nn2c(Br)ccc(OC)c2c1[N+](=O)[O-].COc1cc(C)cc(C)c1OB(O)O>>CCc1nn2c(-c3c(C)cc(C)cc3OC)ccc(OC)c2c1[N+](=O)[O-] | CC1=CC(=C(C(=C1)C)OB(O)O)OC.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].BrC1=CC=C(C=2N1N=C(C2[N+](=O)[O-])CC)OC>>C(C)C1=NN2C(C(=CC=C2C2=C(C=C(C=C2C)C)OC)OC)=C1[N+](=O)[O-] | Br[c:6]1[n:5]2[n:4][c:3]([CH2:2][CH3:1])[c:23]([N+:24](=[O:25])[O-:26])[c:22]2[c:19]([O:20][CH3:21])[cH:18][cH:17]1.OB(O)O[c:7]1[c:8]([CH3:9])[cH:10][c:11]([CH3:12])[cH:13][c:14]1[O:15][CH3:16]>>[CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[c:8]([CH3:9])[cH:10][c:11]([CH3:12])[cH:13][c:14]3[O:15][CH3:16])[cH:17][cH:18][... | CCc1nn2c(Br)ccc(OC)c2c1[N+](=O)[O-].COc1cc(C)cc(C)c1OB(O)O | CCc1nn2c(-c3c(C)cc(C)cc3OC)ccc(OC)c2c1[N+](=O)[O-] | 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 | C(C)OCCOCC.O | C-C Coupling | OtherReaction | 8b93332ffb86325cf5e747a3ea9faae13848b7451cf269888446bfaf73495994 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2cccc3ccnn23)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[#7;a:4](:[c:5]):[#7;a:6]:[c:7].O-B(-O)-O-[c;H0;D3;+0:8](:[c:9](-[#8:10]):[c:11]):[c:12](-[C;D1;H3:13]):[c:14]>>[#8:10]-[c:9](:[c:11]):[c;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[#7;a:4](:[c:5]):[#7;a:6]:[c:7]):[c:12](-[C;D1;H3:13]):[c:14] | 98.3 | [{"value": 98.3, "product": "C(C)C1=NN2C(C(=CC=C2C2=C(C=C(C=C2C)C)OC)OC)=C1[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | After adding 4,6-dimethyl-2-methoxyphenylboric acid (191 mg), barium hydroxide octahydrate (334 mg) and tetrakis(triphenylphosphine)palladium (0) complex (123 mg) to a solution of 7-bromo-2-ethyl-4-methoxy-3-nitropyrazolo[1,5-a]pyridine (159 mg) in a mixture of ethyleneglycol diethyl ether (15 mL) and water (7.5 mL), t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccn2nccc2c1.c1ccccc1 | c1ccccc1.c1ccn2nccc2c1 | c1ccccc1.c1ccn2nccc2c1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)OCCOCC.O | 80 | null | CCc1nn2c(Br)ccc(OC)c2c1[N+](=O)[O-].COc1cc(C)cc(C)c1OB(O)O>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.C(C)OCCOCC.O>CCc1nn2c(-c3c(C)cc(C)cc3OC)ccc(OC)c2c1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1ccdaf7056bb4b19ac2246f9eba30bca | CSc1nn2ccccc2c1NC(=O)OC(C)(C)C.ICCI>>CSc1nn2c(I)cccc2c1NC(=O)OC(C)(C)C | [Cl-].[NH4+].ICCI.CSC1=NN2C(C=CC=C2)=C1NC(OC(C)(C)C)=O.C(CCC)[Li]>>IC1=CC=CC=2N1N=C(C2NC(OC(C)(C)C)=O)SC | [CH3:1][S:2][c:3]1[n:4][n:5]2[cH:6][cH:8][cH:9][cH:10][c:11]2[c:12]1[NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20].ICC[I:7]>>[CH3:1][S:2][c:3]1[n:4][n:5]2[c:6]([I:7])[cH:8][cH:9][cH:10][c:11]2[c:12]1[NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20] | CSc1nn2ccccc2c1NC(=O)OC(C)(C)C.ICCI | CSc1nn2c(I)cccc2c1NC(=O)OC(C)(C)C | null | null | O1CCCC1.CCCCCC | Functional Group Interconversion | OtherReaction | 45f2a64fd76bc339669d027148c9d9ecf1f240b29ad0040207cebf4b091ffdba | a8fd90d9727001deb7b4d3f63c2c94d8100018754aab15c0aa879096d979fed2 | c1ccn2nccc2c1 | I-C-C-[I;H0;D1;+0:1].[c:2]:[#7;a:3](:[#7;a:4]:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[I;H0;D1;+0:1]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[#7;a:3](:[c:2]):[#7;a:4]:[c:5] | null | [] | null | null | 30 | MINUTE | After dissolving tert-butyl N-[2-methylthiopyrazolo[1,5-a]pyridin-3-yl]carbamate (21.6 g) in tetrahydrofuran (1 L), a solution of n-butyllithium in hexane (1.6 M; 130 mL) was added dropwise at −78° C. under a nitrogen stream, and the mixture was stirred for 30 minutes. A solution of 1,2-diiodoethane (24 g) in tetrahydr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | Aromatic halide | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1ccn2nccc2c1 | HI | O1CCCC1.CCCCCC | null | 0.5 | CSc1nn2ccccc2c1NC(=O)OC(C)(C)C.ICCI>O1CCCC1.CCCCCC>CSc1nn2c(I)cccc2c1NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0fcd62becadc4836ba07d9659cf62752 | COc1cc2ccccn2n1.ClC(Cl)(Br)C(Cl)(Cl)Br>>COc1cc2cccc(Br)n2n1 | COC1=NN2C(C=CC=C2)=C1.BrC(C(Cl)(Cl)Br)(Cl)Cl.C(CCC)[Li]>>BrC1=CC=CC=2N1N=C(C2)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][n:11]2[n:12]1.ClC(Cl)(Br)C(Cl)(Cl)[Br:10]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([Br:10])[n:11]2[n:12]1 | COc1cc2ccccn2n1.ClC(Cl)(Br)C(Cl)(Cl)Br | COc1cc2cccc(Br)n2n1 | null | null | O1CCCC1.CCCCCC | Functional Group Interconversion | Bromination | 239df31471b347eeb51abec73301027b6f1036c85391671e1491db98f67e85bb | 019ad5fd0dfe62cfb4244afde83961e2345586820445df7561489ed4a5d090fa | c1ccn2nccc2c1 | Br-C(-Cl)(-Cl)-C(-Cl)(-Cl)-[Br;H0;D1;+0:1].[c:2]:[#7;a:3]:[#7;a:4](:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[#7;a:4](:[c:5]):[#7;a:3]:[c:2] | 64.8 | [{"value": 64.8, "product": "BrC1=CC=CC=2N1N=C(C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 2-methoxypyrazolo[1,5-a]pyridine (7.15 g) [CAS No.59942-88-0] in tetrahydrofuran (140 mL) was cooled to −78° C. under a nitrogen stream, and then a solution of n-butyllithium in hexane (1.6 M; 46 mL) was added dropwise and the mixture was stirred for 30 minutes. A solution of 1,2-dibromo-1,1,2,2-tetrachlo... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide | Aromatic halide | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1ccn2nccc2c1 | HCl.Br- | O1CCCC1.CCCCCC | null | 0.5 | COc1cc2ccccn2n1.ClC(Cl)(Br)C(Cl)(Cl)Br>O1CCCC1.CCCCCC>COc1cc2cccc(Br)n2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ef355f3f2c124d5b957d21085f07d951 | COc1cc2cccc(Br)n2n1>>COc1nn2c(Br)cccc2c1N=O | BrC1=CC=CC=2N1N=C(C2)OC.N(=O)[O-].[Na+]>>BrC1=CC=CC=2N1N=C(C2N=O)OC | [CH3:1][O:2][c:3]1[n:4][n:5]2[c:6]([Br:7])[cH:8][cH:9][cH:10][c:11]2[cH:12]1>>[CH3:1][O:2][c:3]1[n:4][n:5]2[c:6]([Br:7])[cH:8][cH:9][cH:10][c:11]2[c:12]1[N:13]=[O:14] | COc1cc2cccc(Br)n2n1 | COc1nn2c(Br)cccc2c1N=O | null | null | C(C)(=O)O | Functional Group Addition | OtherReaction | 4b02f502982406631ebbebfd6fef99bbb24047f7cb58e0c34794359c7b70b197 | c852dfd7a307035d7b21dc79db1d13bba1cfffe7578c3caa265be3f4f0c038c5 | c1ccn2nccc2c1 | [#8:1]-[c:2]1:[#7;a:3]:[#7;a:4](:[c:5]):[c:6](:[c:7]):[cH;D2;+0:8]:1>>[#8:1]-[c:2]1:[#7;a:3]:[#7;a:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8]:1-[#7:9]=[O;D1;H0:10] | null | [] | null | null | 30 | MINUTE | After dissolving 7-bromo-2-methoxypyrazolo[1,5-a]pyridine (400 mg) in acetic acid (4 mL), an aqueous solution (2 mL) containing sodium nitrite (134 mg) was added and the mixture was stirred at room temperature for 30 minutes. The precipitated crystals were collected by filtration and washed with water. After dissolving... | 10.6084/m9.figshare.5104873.v1 | null | null | Nitroso | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1ccn2nccc2c1 | Other | C(C)(=O)O | null | 0.5 | COc1cc2cccc(Br)n2n1>C(C)(=O)O>COc1nn2c(Br)cccc2c1N=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-52c83a0963b84c5a9ed2f488112b8ecf | COc1cc2cccc(Br)n2n1>>COc1nn2c(Br)cccc2c1N | N(=O)[O-].[Na+].BrC1=CC=CC=2N1N=C(C2)OC.C(C)O.O>>BrC1=CC=CC=2N1N=C(C2N)OC | [CH3:1][O:2][c:3]1[n:4][n:5]2[c:6]([Br:7])[cH:8][cH:9][cH:10][c:11]2[cH:12]1>>[CH3:1][O:2][c:3]1[n:4][n:5]2[c:6]([Br:7])[cH:8][cH:9][cH:10][c:11]2[c:12]1[NH2:13] | COc1cc2cccc(Br)n2n1 | COc1nn2c(Br)cccc2c1N | null | [Zn] | C(C)(=O)O | Functional Group Addition | OtherReaction | 6262fd7e727d841fb73851c8f5fc12593180081a96f2740304439e941350e2f8 | d69ce1fde4173969963123914389bef807fad83b73b8a587195a7122d5cdf1d2 | c1ccn2nccc2c1 | [#8:1]-[c:2]1:[#7;a:3]:[#7;a:4](:[c:5]):[c:6](:[c:7]):[cH;D2;+0:8]:1>>[#8:1]-[c:2]1:[#7;a:3]:[#7;a:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8]:1-[N;D1;H2:9] | 70.3 | [{"value": 70.3, "product": "BrC1=CC=CC=2N1N=C(C2N)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | After dissolving 7-bromo-2-methoxypyrazolo[1,5-a]pyridine (1 g) in acetic acid (10 mL), an aqueous solution (5 mL) containing sodium nitrite (334 mg) was added and the mixture was stirred at room temperature for 20 minutes. After adding ethanol (60 mL) and water (30 mL) to the reaction mixture, zinc powder (1 g) was ad... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1ccn2nccc2c1 | Other | [Zn].C(C)(=O)O | null | 0.333333 | COc1cc2cccc(Br)n2n1>[Zn].C(C)(=O)O>COc1nn2c(Br)cccc2c1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f6b1679482d14db0b11eddb742d1b067 | CCOB(OCC)OCC.CSc1nn2c(I)cccc2c1NC(=O)OC(C)(C)C>>CSc1nn2c(OB(O)O)cccc2c1NC(=O)OC(C)(C)C | [Cl-].[NH4+].C(CCC)[Li].IC1=CC=CC=2N1N=C(C2NC(OC(C)(C)C)=O)SC.C(C)OB(OCC)OCC>>C(C)(C)(C)OC(=O)NC=1C(=NN2C1C=CC=C2OB(O)O)SC | CC[O:7][B:8]([O:9]CC)[O:10]CC.I[c:6]1[n:5]2[n:4][c:3]([S:2][CH3:1])[c:15]([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[c:14]2[cH:13][cH:12][cH:11]1>>[CH3:1][S:2][c:3]1[n:4][n:5]2[c:6]([O:7][B:8]([OH:9])[OH:10])[cH:11][cH:12][cH:13][c:14]2[c:15]1[NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[C... | CCOB(OCC)OCC.CSc1nn2c(I)cccc2c1NC(=O)OC(C)(C)C | CSc1nn2c(OB(O)O)cccc2c1NC(=O)OC(C)(C)C | null | null | C(C)(=O)OCC.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 810ae7d975735b006e602e09982cbde75f8a6d5ce6fe6c5403a0ef408492c5ce | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccn2nccc2c1 | C-C-[O;H0;D2;+0:1]-[#5:2](-[O;H0;D2;+0:3]-C-C)-[O;H0;D2;+0:4]-C-C.I-[c;H0;D3;+0:5](:[c:6]:[c:7]):[#7;a:8](:[c:9]):[#7;a:10]:[c:11]>>[OH;D1;+0:1]-[#5:2](-[OH;D1;+0:4])-[O;H0;D2;+0:3]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[#7;a:8](:[c:9]):[#7;a:10]:[c:11] | null | [] | -78 | CELSIUS | null | null | After dissolving tert-butyl N-(7-iodo-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl)carbamate (200 mg) in tetrahydrofuran (2 mL), the mixture was cooled to −78° C. and n-butyllithium (1.6 M; 0.66 mL) was added dropwise. The mixture was stirred for 1-hour at the same temperature, triethoxyborane (109 μL) was added and t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1ccn2nccc2c1 | HI | C(C)(=O)OCC.O1CCCC1 | -78 | null | CCOB(OCC)OCC.CSc1nn2c(I)cccc2c1NC(=O)OC(C)(C)C>C(C)(=O)OCC.O1CCCC1>CSc1nn2c(OB(O)O)cccc2c1NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ec0bfdfdbef34fc5a67d159cbe715afc | CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1[N+](=O)[O-]>>CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1N | O.C(C)(=O)O.ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2[N+](=O)[O-])CC>>ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2N)CC | O=[N+:20]([O-])[c:19]1[c:3]([CH2:2][CH3:1])[n:4][n:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]3[Cl:14])[cH:15][cH:16][cH:17][c:18]21>>[CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]3[Cl:14])[cH:15][cH:16][cH:17][c:18]2[c:19]1[NH2:20] | CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1[N+](=O)[O-] | CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1N | null | [Zn] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2cccc3ccnn23)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3](:[c:4]):[#7;a:5](:[c:6]):[#7;a:7]:[c:8]:1-[C:9]>>[C:9]-[c:8]1:[#7;a:7]:[#7;a:5](:[c:6]):[c:3](:[c:4]):[c:2]:1-[NH2;D1;+0:1] | 89.8 | [{"value": 89.8, "product": "ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2N)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | 7-(2,4-Dichlorophenyl)-2-ethyl-3-nitropyrazolo[1,5-a]pyridine (110 mg) was suspended in ethanol (6 mL), and then water (3 mL), acetic acid (1 mL) and zinc powder (220 mg) were added and the mixture was heated and stirred at 60° C. for 1 hour. The reaction mixture was filtered, water was added to the filtrate, extractio... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccn2nccc2c1 | Other | [Zn].C(C)O | 60 | 1 | CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1[N+](=O)[O-]>[Zn].C(C)O>CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3ab709c49b514c698590f2525c78e682 | CCc1nn2c(-c3ccc(OC)cc3Cl)cccc2c1[N+](=O)[O-]>>CCc1nn2c(-c3ccc(OC)cc3Cl)cccc2c1N | O.C(C)(=O)O.ClC1=C(C=CC(=C1)OC)C1=CC=CC=2N1N=C(C2[N+](=O)[O-])CC>>ClC1=C(C=CC(=C1)OC)C1=CC=CC=2N1N=C(C2N)CC | O=[N+:21]([O-])[c:20]1[c:3]([CH2:2][CH3:1])[n:4][n:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][c:14]3[Cl:15])[cH:16][cH:17][cH:18][c:19]21>>[CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][c:14]3[Cl:15])[cH:16][cH:17][cH:18][c:19]2[c:20]1[NH2:21] | CCc1nn2c(-c3ccc(OC)cc3Cl)cccc2c1[N+](=O)[O-] | CCc1nn2c(-c3ccc(OC)cc3Cl)cccc2c1N | null | [Zn] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2cccc3ccnn23)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3](:[c:4]):[#7;a:5](:[c:6]):[#7;a:7]:[c:8]:1-[C:9]>>[C:9]-[c:8]1:[#7;a:7]:[#7;a:5](:[c:6]):[c:3](:[c:4]):[c:2]:1-[NH2;D1;+0:1] | null | [] | 80 | CELSIUS | 30 | MINUTE | 7-(2-Chloro-4-methoxyphenyl)-2-ethyl-3-nitropyrazolo[1,5-a]pyridine (5 mg) was suspended in ethanol (2 mL), and then water (1 mL), acetic acid (0.5 mL) and zinc powder (10 mg) were added and the mixture was heated and stirred at 80° C. for 30 minutes. The reaction mixture was filtered, water was added to the filtrate, ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccn2nccc2c1 | Other | [Zn].C(C)O | 80 | 0.5 | CCc1nn2c(-c3ccc(OC)cc3Cl)cccc2c1[N+](=O)[O-]>[Zn].C(C)O>CCc1nn2c(-c3ccc(OC)cc3Cl)cccc2c1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ff5644163a6b494b9ede73774b11d44a | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1N>>CCCC(CC)Nc1c(CC)nn2c(-c3ccc(Cl)cc3Cl)cccc12 | O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2N)CC.S(=O)(=O)([O-])[O-].[Na+].[Na+]>>ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2NC(CC)CCC)CC | O=[C:1](O[BH-](O[C:2](=O)[CH3:3])O[C:4](=O)[CH3:5])[CH3:6].[NH2:7][c:8]1[c:9]([CH2:10][CH3:11])[n:12][n:13]2[c:14](-[c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]3[Cl:22])[cH:23][cH:24][cH:25][c:26]12>>[CH3:1][CH2:2][CH2:3][CH:4]([CH2:5][CH3:6])[NH:7][c:8]1[c:9]([CH2:10][CH3:11])[n:12][n:13]2[c:14](-[c:15]3[cH:16][c... | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1N | CCCC(CC)Nc1c(CC)nn2c(-c3ccc(Cl)cc3Cl)cccc12 | null | null | C(C)(=O)O.CCC(CCC)=O.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 3c2788b3f372b76c1d2ee0d77963cb247b210aa8a28e76637b4e731826c4252a | c6874c6af41d3b1c4f7668e1cd342c90252d0e77f4317d31b3193ebc2f9501a3 | c1ccc(-c2cccc3ccnn23)cc1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-O-[BH-](-O-[C;H0;D3;+0:3](=O)-[CH3;D1;+0:4])-O-[C;H0;D3;+0:5](=O)-[CH3;D1;+0:6].[C:7]-[c:8]1:[#7;a:9]:[#7;a:10](:[c:11]):[c:12](:[c:13]):[c:14]:1-[NH2;D1;+0:15]>>[C:7]-[c:8]1:[#7;a:9]:[#7;a:10](:[c:11]):[c:12](:[c:13]):[c:14]:1-[NH;D2;+0:15]-[CH;D3;+0:5](-[CH2;D2;+0:4]-[CH2;D2;+0:3]-[CH... | 109.8 | [{"value": 109.8, "product": "ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2NC(CC)CCC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | After dissolving [7-(2,4-dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]amine (30 mg) in acetic acid (1 mL), 3-hexanone (0.024 mL) and sodium sulfate (139 mg) were added and the mixture was stirred at room temperature for 30 minutes. Sodium triacetoxyborohydride (41.5 mg) was then added, and stirring was continued ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amine | null | null | c1ccccc1.c1ccn2nccc2c1 | B | C(C)(=O)O.CCC(CCC)=O.C(C)(=O)OCC | null | 0.5 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1N>C(C)(=O)O.CCC(CCC)=O.C(C)(=O)OCC>CCCC(CC)Nc1c(CC)nn2c(-c3ccc(Cl)cc3Cl)cccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ff1ad39d39ca41c0b5fe15c41495f583 | CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1NC(=O)OC(C)(C)C.COCCBr>>CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1NCCOC | [OH-].[Na+].COCCBr.Cl.C(C)(=O)OCC.ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2NC(OC(C)(C)C)=O)CC.[H-].[Na+]>>ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2NCCOC)CC | CC(C)(C)OC(=O)[NH:20][c:19]1[c:3]([CH2:2][CH3:1])[n:4][n:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]3[Cl:14])[cH:15][cH:16][cH:17][c:18]21.Br[CH2:21][CH2:22][O:23][CH3:24]>>[CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[cH:8][cH:9][c:10]([Cl:11])[cH:12][c:13]3[Cl:14])[cH:15][cH:16][cH:17][c:18]2[c:19]1[NH:20... | CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1NC(=O)OC(C)(C)C.COCCBr | CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1NCCOC | null | null | C(C)(=O)OCC.O.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 69c061c6c94f7bb4679b70bacb433db8423283dc2e1b30ca3ecd11460f64261e | f70e997aab372d6ab7cc33008ae9abfd0322142f702e724588c04ad331ebe638 | c1ccc(-c2cccc3ccnn23)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:4]-[c:5]1:[c:6](:[c:7]):[#7;a:8](:[c:9]):[#7;a:10]:[c:11]:1-[C:12]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5]1:[c:6](:[c:7]):[#7;a:8](:[c:9]):[#7;a:10]:[c:11]:1-[C:12] | null | [] | null | null | 1 | HOUR | After dissolving tert-butyl N-[7-(2,4-dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]carbamate (57 mg) in N,N-dimethylformamide (2 mL), sodium hydride (60%, 7.3 mg) was added while cooling on ice, and then 2-bromoethyl methyl ether (0.015 mL) was added and the mixture was stirred for 1 hour. Water was added to the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccccc1.c1ccn2nccc2c1 | HBr | C(C)(=O)OCC.O.CN(C=O)C | null | 1 | CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1NC(=O)OC(C)(C)C.COCCBr>C(C)(=O)OCC.O.CN(C=O)C>CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1NCCOC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5add00d2fc5045eab00f8af0fde67517 | CCC=O.CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1NCCOC>>CCCN(CCOC)c1c(CC)nn2c(-c3ccc(Cl)cc3Cl)cccc12 | ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2NCCOC)CC.C(CC)=O.S(O)(O)(=O)=O.[BH4-].[Na+]>>ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2N(CCC)CCOC)CC | O=[CH:3][CH2:2][CH3:1].[NH:4]([CH2:5][CH2:6][O:7][CH3:8])[c:9]1[c:10]([CH2:11][CH3:12])[n:13][n:14]2[c:15](-[c:16]3[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]3[Cl:23])[cH:24][cH:25][cH:26][c:27]12>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][O:7][CH3:8])[c:9]1[c:10]([CH2:11][CH3:12])[n:13][n:14]2[c:15](-[c:16]3[cH:17][cH:... | CCC=O.CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1NCCOC | CCCN(CCOC)c1c(CC)nn2c(-c3ccc(Cl)cc3Cl)cccc12 | null | null | O.O1CCCC1.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 6d9c60e7c47e75322fc9565d992b855788f3516a27cb14d7f9ed299e190b30d3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(-c2cccc3ccnn23)cc1 | O=[CH;D2;+0:1]-[C:2]-[C;D1;H3:3].[C:4]-[c:5]1:[#7;a:6]:[#7;a:7](:[c:8]):[c:9](:[c:10]):[c:11]:1-[NH;D2;+0:12]-[C:13]-[C:14]>>[C:4]-[c:5]1:[#7;a:6]:[#7;a:7](:[c:8]):[c:9](:[c:10]):[c:11]:1-[N;H0;D3;+0:12](-[C:13]-[C:14])-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3] | null | [] | null | null | 30 | MINUTE | N-[7-(2,4-Dichlorophenyl)-2-ethylpyrazolo[1,5-a]pyridin-3-yl]-N-(2-methoxyethyl)amine (14 mg) was dissolved in tetrahydrofuran (1 mL), and after adding propionaldehyde (0.016 mL) and 3 M aqueous sulfuric acid (0.77 mL), sodium borohydride (5.8 mg) was added in five portions while vigorously stirring on ice, and stirrin... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccn2nccc2c1 | Other | O.O1CCCC1.C(C)OCC | null | 0.5 | CCC=O.CCc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1NCCOC>O.O1CCCC1.C(C)OCC>CCCN(CCOC)c1c(CC)nn2c(-c3ccc(Cl)cc3Cl)cccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0b2809fa27c545c093353b72b8a559f2 | CCc1nn2c(Br)cccc2c1N(CC1CC1)CC1CCOC1.COc1cc(C)c(OB(O)O)c(OC)c1>>CCc1nn2c(-c3c(C)cc(OC)cc3OC)cccc2c1N(CC1CC1)CC1CCOC1 | BrC1=CC=CC=2N1N=C(C2N(CC2COCC2)CC2CC2)CC.COC1=C(C(=CC(=C1)OC)C)OB(O)O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C(C)(=O)OCC>>C1(CC1)CN(CC1COCC1)C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)OC)OC)CC | Br[c:6]1[n:5]2[n:4][c:3]([CH2:2][CH3:1])[c:22]([N:23]([CH2:24][CH:25]3[CH2:26][CH2:27]3)[CH2:28][CH:29]3[CH2:30][CH2:31][O:32][CH2:33]3)[c:21]2[cH:20][cH:19][cH:18]1.OB(O)O[c:7]1[c:8]([CH3:9])[cH:10][c:11]([O:12][CH3:13])[cH:14][c:15]1[O:16][CH3:17]>>[CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[c:8]([CH3:9])[cH:10][c:1... | CCc1nn2c(Br)cccc2c1N(CC1CC1)CC1CCOC1.COc1cc(C)c(OB(O)O)c(OC)c1 | CCc1nn2c(-c3c(C)cc(OC)cc3OC)cccc2c1N(CC1CC1)CC1CCOC1 | 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 | O.COCCOC | C-C Coupling | OtherReaction | 8b93332ffb86325cf5e747a3ea9faae13848b7451cf269888446bfaf73495994 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2cccc3c(N(CC4CC4)CC4CCOC4)cnn23)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[#7;a:4](:[c:5]):[#7;a:6]:[c:7].O-B(-O)-O-[c;H0;D3;+0:8](:[c:9](-[#8:10]):[c:11]):[c:12](-[C;D1;H3:13]):[c:14]>>[#8:10]-[c:9](:[c:11]):[c;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[#7;a:4](:[c:5]):[#7;a:6]:[c:7]):[c:12](-[C;D1;H3:13]):[c:14] | 49.4 | [{"value": 49.4, "product": "C1(CC1)CN(CC1COCC1)C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)OC)OC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 1 | HOUR | After dissolving N-(7-bromo-2-ethylpyrazolo[1,5-a]pyridin-3-yl)-N-cyclopropylmethyl-N-tetrahydro-3-furanylmethylamine (150 mg) in 1,2-dimethoxyethane (20 mL) and water (10 mL), 2,4-dimethoxy-6-methylphenylboric acid (155 mg), tetrakis(triphenylphosphine)palladium (0) complex (92 mg) and barium hydroxide octahydrate (25... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccn2nccc2c1.c1ccccc1 | c1ccccc1.c1ccn2nccc2c1 | c1ccccc1.c1ccn2nccc2c1.C1CC1.C1CCOC1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | 80 | 1 | CCc1nn2c(Br)cccc2c1N(CC1CC1)CC1CCOC1.COc1cc(C)c(OB(O)O)c(OC)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>CCc1nn2c(-c3c(C)cc(OC)cc3OC)cccc2c1N(CC1CC1)CC1CCOC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fd0739025446481b8005125345a3e12d | CCc1nn2c(-c3c(C)cc(C)cc3OC)cccc2c1NCC1CC1.O=CC1CCOCC1>>CCc1nn2c(-c3c(C)cc(C)cc3OC)cccc2c1N(CC1CCOCC1)CC1CC1 | C(O)([O-])=O.[Na+].C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].C1(CC1)CNC=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)CC.O1CCC(CC1)C=O>>C1(CC1)CN(CC1CCOCC1)C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)CC | [CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[c:8]([CH3:9])[cH:10][c:11]([CH3:12])[cH:13][c:14]3[O:15][CH3:16])[cH:17][cH:18][cH:19][c:20]2[c:21]1[NH:22][CH2:30][CH:31]1[CH2:32][CH2:33]1.O=[CH:23][CH:24]1[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1>>[CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[c:8]([CH3:9])[cH:10][c:11]([CH3... | CCc1nn2c(-c3c(C)cc(C)cc3OC)cccc2c1NCC1CC1.O=CC1CCOCC1 | CCc1nn2c(-c3c(C)cc(C)cc3OC)cccc2c1N(CC1CCOCC1)CC1CC1 | null | null | C(C)(=O)OCC.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 6d9c60e7c47e75322fc9565d992b855788f3516a27cb14d7f9ed299e190b30d3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(-c2cccc3c(N(CC4CCOCC4)CC4CC4)cnn23)cc1 | O=[CH;D2;+0:1]-[C:2](-[C:3])-[C:4].[C:5]-[c:6]1:[#7;a:7]:[#7;a:8](:[c:9]):[c:10](:[c:11]):[c:12]:1-[NH;D2;+0:13]-[C:14]-[C:15]>>[C:3]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13](-[C:14]-[C:15])-[c:12]1:[c:10](:[c:11]):[#7;a:8](:[c:9]):[#7;a:7]:[c:6]:1-[C:5])-[C:4] | 41 | [{"value": 41.0, "product": "C1(CC1)CN(CC1CCOCC1)C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | After dissolving N-cyclopropylmethyl-N-[2-ethyl-7-(2-methoxy-4,6-dimethylphenyl)pyrazolo[1,5-a]pyridin-3-yl]amine (255 mg) in tetrahydrofuran (2 mL), tetrahydro-2H-4-pyrancarbaldehyde (173 mg) [CAS No.50675-18-8] and sodium triacetoxyborohydride (241 mg) were added, and the mixture was stirred at room temperature for 1... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccn2nccc2c1.C1CCOCC1.C1CC1 | Other | C(C)(=O)OCC.O1CCCC1 | null | 1 | CCc1nn2c(-c3c(C)cc(C)cc3OC)cccc2c1NCC1CC1.O=CC1CCOCC1>C(C)(=O)OCC.O1CCCC1>CCc1nn2c(-c3c(C)cc(C)cc3OC)cccc2c1N(CC1CCOCC1)CC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-605836c3183744a0b6fa01960338a1b7 | CCc1nn2c(-c3c(C)cc(C)cc3OC)ccc(OC)c2c1[N+](=O)[O-]>>CCc1nn2c(-c3c(C)cc(C)cc3OC)ccc(OC)c2c1N | C(C)C1=NN2C(C(=CC=C2C2=C(C=C(C=C2C)C)OC)OC)=C1[N+](=O)[O-].C(C)(=O)O>>C(C)C1=NN2C(C(=CC=C2C2=C(C=C(C=C2C)C)OC)OC)=C1N | O=[N+:24]([O-])[c:23]1[c:3]([CH2:2][CH3:1])[n:4][n:5]2[c:6](-[c:7]3[c:8]([CH3:9])[cH:10][c:11]([CH3:12])[cH:13][c:14]3[O:15][CH3:16])[cH:17][cH:18][c:19]([O:20][CH3:21])[c:22]21>>[CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[c:8]([CH3:9])[cH:10][c:11]([CH3:12])[cH:13][c:14]3[O:15][CH3:16])[cH:17][cH:18][c:19]([O:20][CH3... | CCc1nn2c(-c3c(C)cc(C)cc3OC)ccc(OC)c2c1[N+](=O)[O-] | CCc1nn2c(-c3c(C)cc(C)cc3OC)ccc(OC)c2c1N | null | [Zn] | O.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2cccc3ccnn23)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3](:[c:4]):[#7;a:5](:[c:6]):[#7;a:7]:[c:8]:1-[C:9]>>[C:9]-[c:8]1:[#7;a:7]:[#7;a:5](:[c:6]):[c:3](:[c:4]):[c:2]:1-[NH2;D1;+0:1] | null | [] | 60 | CELSIUS | null | null | 2-Ethyl-4-methoxy-7-(2-methoxy-4,6-dimethylphenyl)-3-nitropyrazolo[1,5-a]pyridine (185 mg) was dissolved in a mixture of ethanol (7 mL) and water (7.5 mL), and then acetic acid (0.3 mL) and zinc powder (185 mg) were added and the reaction mixture was heated at 60° C. for 20 minutes. The reaction mixture was filtered wi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccn2nccc2c1 | Other | [Zn].O.C(C)O | 60 | null | CCc1nn2c(-c3c(C)cc(C)cc3OC)ccc(OC)c2c1[N+](=O)[O-]>[Zn].O.C(C)O>CCc1nn2c(-c3c(C)cc(C)cc3OC)ccc(OC)c2c1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bf2e18615a834fdc9d01496b0f8b0599 | CCC(=O)CC.CCc1nn2c(-c3c(C)cc(C)cc3OC)ccc(OC)c2c1N>>CCc1nn2c(-c3c(C)cc(C)cc3OC)ccc(OC)c2c1NC(CC)CC | [OH-].[Na+].C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].C(C)C1=NN2C(C(=CC=C2C2=C(C=C(C=C2C)C)OC)OC)=C1N.CCC(CC)=O>>C(C)C1=NN2C(C(=CC=C2C2=C(C=C(C=C2C)C)OC)OC)=C1NC(CC)CC | O=[C:25]([CH2:26][CH3:27])[CH2:28][CH3:29].[CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[c:8]([CH3:9])[cH:10][c:11]([CH3:12])[cH:13][c:14]3[O:15][CH3:16])[cH:17][cH:18][c:19]([O:20][CH3:21])[c:22]2[c:23]1[NH2:24]>>[CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[c:8]([CH3:9])[cH:10][c:11]([CH3:12])[cH:13][c:14]3[O:15][CH3:1... | CCC(=O)CC.CCc1nn2c(-c3c(C)cc(C)cc3OC)ccc(OC)c2c1N | CCc1nn2c(-c3c(C)cc(C)cc3OC)ccc(OC)c2c1NC(CC)CC | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(-c2cccc3ccnn23)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C;D1;H3:3])-[C:4]-[C;D1;H3:5].[C:6]-[c:7]1:[#7;a:8]:[#7;a:9](:[c:10]):[c:11](:[c:12]):[c:13]:1-[NH2;D1;+0:14]>>[C:6]-[c:7]1:[#7;a:8]:[#7;a:9](:[c:10]):[c:11](:[c:12]):[c:13]:1-[NH;D2;+0:14]-[CH;D3;+0:1](-[C:2]-[C;D1;H3:3])-[C:4]-[C;D1;H3:5] | null | [] | null | null | 3 | HOUR | To a solution of 2-ethyl-4-methoxy-7-(2-methoxy-4,6-dimethylphenyl)pyrazolo[1,5-a]pyridin-3-amine (100 mg) in acetic acid (10 mL) there was added 3-pentanone (0.04 mL), and then sodium triacetoxyborohydride (85.0 mg) was slowly added at room temperature and the mixture was stirred for 3 hours. A 5 N aqueous sodium hydr... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccn2nccc2c1 | Other | C(C)(=O)O | null | 3 | CCC(=O)CC.CCc1nn2c(-c3c(C)cc(C)cc3OC)ccc(OC)c2c1N>C(C)(=O)O>CCc1nn2c(-c3c(C)cc(C)cc3OC)ccc(OC)c2c1NC(CC)CC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0692695576e7425892dd86a2661444ee | CSc1nn2ccccc2c1NC(=O)OC(C)(C)C.ClC(Cl)(Br)C(Cl)(Cl)Br>>CSc1nn2c(Br)cccc2c1NC(=O)OC(C)(C)C | [Cl-].[NH4+].BrC(C(Cl)(Cl)Br)(Cl)Cl.CSC1=NN2C(C=CC=C2)=C1NC(OC(C)(C)C)=O.C(CCC)[Li]>>BrC1=CC=CC=2N1N=C(C2NC(OC(C)(C)C)=O)SC | [CH3:1][S:2][c:3]1[n:4][n:5]2[cH:6][cH:8][cH:9][cH:10][c:11]2[c:12]1[NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20].ClC(Cl)(Br)C(Cl)(Cl)[Br:7]>>[CH3:1][S:2][c:3]1[n:4][n:5]2[c:6]([Br:7])[cH:8][cH:9][cH:10][c:11]2[c:12]1[NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20] | CSc1nn2ccccc2c1NC(=O)OC(C)(C)C.ClC(Cl)(Br)C(Cl)(Cl)Br | CSc1nn2c(Br)cccc2c1NC(=O)OC(C)(C)C | null | null | O1CCCC1.CCCCCC | Functional Group Interconversion | Bromination | 239df31471b347eeb51abec73301027b6f1036c85391671e1491db98f67e85bb | 019ad5fd0dfe62cfb4244afde83961e2345586820445df7561489ed4a5d090fa | c1ccn2nccc2c1 | Br-C(-Cl)(-Cl)-C(-Cl)(-Cl)-[Br;H0;D1;+0:1].[c:2]:[#7;a:3](:[#7;a:4]:[c:5]):[cH;D2;+0:6]:[c:7]:[c:8]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[#7;a:3](:[c:2]):[#7;a:4]:[c:5] | null | [] | null | null | 30 | MINUTE | After dissolving tert-butyl N-[2-methylthiopyrazolo[1,5-a]pyridin-3-yl]carbamate (220 mg) in tetrahydrofuran (3 mL), a solution of n-butyllithium in hexane (1.6 M; 1.51 mL) was added dropwise at −78° C. under a nitrogen stream, and the mixture was stirred for 30 minutes. A solution of 1,2-dibromo-1,1,2,2-tetrachloroeth... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide | Aromatic halide | c1ccn2nccc2c1 | c1ccn2nccc2c1 | c1ccn2nccc2c1 | HCl.Br- | O1CCCC1.CCCCCC | null | 0.5 | CSc1nn2ccccc2c1NC(=O)OC(C)(C)C.ClC(Cl)(Br)C(Cl)(Cl)Br>O1CCCC1.CCCCCC>CSc1nn2c(Br)cccc2c1NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-85ce8db2a3f641468494fb3dc183a994 | COc1cc(C)cc(C)c1OB(O)O.CSc1nn2c(I)cccc2c1NC(=O)OC(C)(C)C>>COc1cc(C)cc(C)c1-c1cccc2c(NC(=O)OC(C)(C)C)c(SC)nn12 | IC1=CC=CC=2N1N=C(C2NC(OC(C)(C)C)=O)SC.CC1=CC(=C(C(=C1)C)OB(O)O)OC.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C(C)(=O)OCC>>COC1=C(C(=CC(=C1)C)C)C1=CC=CC=2N1N=C(C2NC(OC(C)(C)C)=O)SC | OB(O)O[c:10]1[c:3]([O:2][CH3:1])[cH:4][c:5]([CH3:6])[cH:7][c:8]1[CH3:9].I[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[c:25]([S:26][CH3:27])[n:28][n:29]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:... | COc1cc(C)cc(C)c1OB(O)O.CSc1nn2c(I)cccc2c1NC(=O)OC(C)(C)C | COc1cc(C)cc(C)c1-c1cccc2c(NC(=O)OC(C)(C)C)c(SC)nn12 | 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 | O.COCCOC | C-C Coupling | OtherReaction | 8b93332ffb86325cf5e747a3ea9faae13848b7451cf269888446bfaf73495994 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2cccc3ccnn23)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[#7;a:4](:[c:5]):[#7;a:6]:[c:7].O-B(-O)-O-[c;H0;D3;+0:8](:[c:9](-[#8:10]):[c:11]):[c:12](-[C;D1;H3:13]):[c:14]>>[#8:10]-[c:9](:[c:11]):[c;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[#7;a:4](:[c:5]):[#7;a:6]:[c:7]):[c:12](-[C;D1;H3:13]):[c:14] | 102.9 | [{"value": 102.9, "product": "COC1=C(C(=CC(=C1)C)C)C1=CC=CC=2N1N=C(C2NC(OC(C)(C)C)=O)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 3 | HOUR | After dissolving tert-butyl N-[7-iodo-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate (2.0 g) in 1,2-dimethoxyethane (60 mL) and water (30 mL), 4,6-dimethyl-2-methoxyphenylboric acid (1.33 g), tetrakis(triphenylphosphine)palladium (0) complex (865 mg) and barium hydroxide octahydrate (2.34 g) were added and the... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1ccn2nccc2c1 | c1ccccc1.c1ccn2nccc2c1 | c1ccccc1.c1ccn2nccc2c1 | HI.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | 80 | 3 | COc1cc(C)cc(C)c1OB(O)O.CSc1nn2c(I)cccc2c1NC(=O)OC(C)(C)C>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>COc1cc(C)cc(C)c1-c1cccc2c(NC(=O)OC(C)(C)C)c(SC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ac823638d3774542976566958b9ec3a3 | BrCC1CC1.COc1cc(C)cc(C)c1-c1cccc2c(NC(=O)OC(C)(C)C)c(SC)nn12>>COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)C(=O)OC(C)(C)C)c(SC)nn12 | O.BrCC1CC1.COC1=C(C(=CC(=C1)C)C)C1=CC=CC=2N1N=C(C2NC(OC(C)(C)C)=O)SC.[H-].[Na+]>>C1(CC1)CN(C(OC(C)(C)C)=O)C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)SC | Br[CH2:18][CH:19]1[CH2:20][CH2:21]1.[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]([NH:17][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[c:29]([S:30][CH3:31])[n:32][n:33]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[c... | BrCC1CC1.COc1cc(C)cc(C)c1-c1cccc2c(NC(=O)OC(C)(C)C)c(SC)nn12 | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)C(=O)OC(C)(C)C)c(SC)nn12 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 5da873da5e065666521679df8db5a1d2754540edd93ae40997847c9a24dedeb3 | c05cd517c346aa4e8e8e58218c491edaea33d354b5dba9eb90dac8ad97104f73 | c1ccc(-c2cccc3c(NCC4CC4)cnn23)cc1 | Br-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[#16:5]-[c:6]1:[#7;a:7]:[#7;a:8](:[c:9]):[c:10](:[c:11]):[c:12]:1-[NH;D2;+0:13]-[C:14](=[O;D1;H0:15])-[#8:16]-[C:17](-[C;D1;H3:18])(-[C;D1;H3:19])-[C;D1;H3:20]>>[#16:5]-[c:6]1:[#7;a:7]:[#7;a:8](:[c:9]):[c:10](:[c:11]):[c:12]:1-[N;H0;D3;+0:13](-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1)-[C... | null | [] | 40 | CELSIUS | 1 | HOUR | After dissolving tert-butyl N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate (400 mg) in N,N-dimethylformamide (5 mL), sodium hydride (60%, 58 mg) was added while cooling on ice, and then (bromomethyl)cyclopropane (111 μL) was added and the mixture was stirred for 1 hour at 40... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester | Carbamic ester | null | null | c1ccccc1.C1CC1.c1ccn2nccc2c1 | HBr | CN(C=O)C.C(C)(=O)OCC | 40 | 1 | BrCC1CC1.COc1cc(C)cc(C)c1-c1cccc2c(NC(=O)OC(C)(C)C)c(SC)nn12>CN(C=O)C.C(C)(=O)OCC>COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)C(=O)OC(C)(C)C)c(SC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-40db0070c5434809be40bc5733401f02 | COc1cc(C)cc(C)c1-c1cccc2c(NC(=O)OC(C)(C)C)c(SC)nn12>>COc1cc(C)cc(C)c1-c1cccc2c(N)c(SC)nn12 | COC1=C(C(=CC(=C1)C)C)C1=CC=CC=2N1N=C(C2NC(OC(C)(C)C)=O)SC.[OH-].[Na+]>>COC1=C(C(=CC(=C1)C)C)C1=CC=CC=2N1N=C(C2N)SC | CC(C)(C)OC(=O)[NH:17][c:16]1[c:15]2[cH:14][cH:13][cH:12][c:11](-[c:10]3[c:3]([O:2][CH3:1])[cH:4][c:5]([CH3:6])[cH:7][c:8]3[CH3:9])[n:22]2[n:21][c:18]1[S:19][CH3:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]([NH2:17])[c:18]([S:19][CH3:20])[n:21][n:22]12 | COc1cc(C)cc(C)c1-c1cccc2c(NC(=O)OC(C)(C)C)c(SC)nn12 | COc1cc(C)cc(C)c1-c1cccc2c(N)c(SC)nn12 | null | null | Cl.C(C)(=O)OCC | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(-c2cccc3ccnn23)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]1:[c:3](:[c:4]):[#7;a:5](:[c:6]):[#7;a:7]:[c:8]:1-[#16:9]>>[#16:9]-[c:8]1:[#7;a:7]:[#7;a:5](:[c:6]):[c:3](:[c:4]):[c:2]:1-[NH2;D1;+0:1] | null | [] | null | null | 1 | HOUR | tert-Butyl N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate (50 mg) was dissolved in a 4 N hydrochloric acid/ethyl acetate solution (2 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was neutralized with 5 N aqueous sodium hydroxide and ex... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccn2nccc2c1 | HO- | Cl.C(C)(=O)OCC | null | 1 | COc1cc(C)cc(C)c1-c1cccc2c(NC(=O)OC(C)(C)C)c(SC)nn12>Cl.C(C)(=O)OCC>COc1cc(C)cc(C)c1-c1cccc2c(N)c(SC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d6d9ef502a3f4df18fbb4eeb81fb5ea4 | CCCI.CSc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1NC(=O)OC(C)(C)C>>CCCNc1c(SC)nn2c(-c3ccc(Cl)cc3Cl)cccc12 | [OH-].[Na+].ICCC.Cl.C(C)(=O)OCC.ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2NC(OC(C)(C)C)=O)SC.[H-].[Na+]>>ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2NCCC)SC | I[CH2:3][CH2:2][CH3:1].CC(C)(C)OC(=O)[NH:4][c:5]1[c:6]([S:7][CH3:8])[n:9][n:10]2[c:11](-[c:12]3[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]3[Cl:19])[cH:20][cH:21][cH:22][c:23]12>>[CH3:1][CH2:2][CH2:3][NH:4][c:5]1[c:6]([S:7][CH3:8])[n:9][n:10]2[c:11](-[c:12]3[cH:13][cH:14][c:15]([Cl:16])[cH:17][c:18]3[Cl:19])[cH:20][cH:21... | CCCI.CSc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1NC(=O)OC(C)(C)C | CCCNc1c(SC)nn2c(-c3ccc(Cl)cc3Cl)cccc12 | null | null | C(C)(=O)OCC.O.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 69c061c6c94f7bb4679b70bacb433db8423283dc2e1b30ca3ecd11460f64261e | f70e997aab372d6ab7cc33008ae9abfd0322142f702e724588c04ad331ebe638 | c1ccc(-c2cccc3ccnn23)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]1:[c:3](:[c:4]):[#7;a:5](:[c:6]):[#7;a:7]:[c:8]:1-[#16:9].I-[CH2;D2;+0:10]-[C:11]-[C;D1;H3:12]>>[#16:9]-[c:8]1:[#7;a:7]:[#7;a:5](:[c:6]):[c:3](:[c:4]):[c:2]:1-[NH;D2;+0:1]-[CH2;D2;+0:10]-[C:11]-[C;D1;H3:12] | null | [] | null | null | 30 | MINUTE | After dissolving tert-butyl N-[7-(2,4-dichlorophenyl)-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]carbamate (150 mg) in N,N-dimethylformamide (3 mL), sodium hydride (60%, 21 mg) was added while cooling on ice, and then 1-iodopropane (0.041 mL) was added and the mixture was stirred for 30 minutes. Water was added to the rea... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccccc1.c1ccn2nccc2c1 | HI | C(C)(=O)OCC.O.CN(C=O)C | null | 0.5 | CCCI.CSc1nn2c(-c3ccc(Cl)cc3Cl)cccc2c1NC(=O)OC(C)(C)C>C(C)(=O)OCC.O.CN(C=O)C>CCCNc1c(SC)nn2c(-c3ccc(Cl)cc3Cl)cccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-37c8ee7b959f4025b20c8210680cbd20 | CCC=O.CCCNc1c(SC)nn2c(-c3ccc(Cl)cc3Cl)cccc12>>CCCN(CCC)c1c(SC)nn2c(-c3ccc(Cl)cc3Cl)cccc12 | ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2NCCC)SC.C(CC)=O.S(O)(O)(=O)=O.[BH4-].[Na+]>>ClC1=C(C=CC(=C1)Cl)C1=CC=CC=2N1N=C(C2N(CCC)CCC)SC | O=[CH:5][CH2:6][CH3:7].[CH3:1][CH2:2][CH2:3][NH:4][c:8]1[c:9]([S:10][CH3:11])[n:12][n:13]2[c:14](-[c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]3[Cl:22])[cH:23][cH:24][cH:25][c:26]12>>[CH3:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][CH3:7])[c:8]1[c:9]([S:10][CH3:11])[n:12][n:13]2[c:14](-[c:15]3[cH:16][cH:17][c:18]([Cl:19])... | CCC=O.CCCNc1c(SC)nn2c(-c3ccc(Cl)cc3Cl)cccc12 | CCCN(CCC)c1c(SC)nn2c(-c3ccc(Cl)cc3Cl)cccc12 | null | null | O.O1CCCC1.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 6d9c60e7c47e75322fc9565d992b855788f3516a27cb14d7f9ed299e190b30d3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(-c2cccc3ccnn23)cc1 | O=[CH;D2;+0:1]-[C:2]-[C;D1;H3:3].[#16:4]-[c:5]1:[#7;a:6]:[#7;a:7](:[c:8]):[c:9](:[c:10]):[c:11]:1-[NH;D2;+0:12]-[C:13]-[C:14]>>[#16:4]-[c:5]1:[#7;a:6]:[#7;a:7](:[c:8]):[c:9](:[c:10]):[c:11]:1-[N;H0;D3;+0:12](-[C:13]-[C:14])-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3] | null | [] | null | null | 30 | MINUTE | N-[7-(2,4-dichlorophenyl)-2-methylthiopyrazolo[1,5-a]pyridin-3-yl]-N-propylamine (59 mg) was dissolved in tetrahydrofuran (1 mL), and after adding propionaldehyde (0.035 mL) and 3 M aqueous sulfuric acid (0.16 mL), sodium borohydride (12 mg) was added in five portions while vigorously stirring on ice, and stirring was ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccn2nccc2c1 | Other | O.O1CCCC1.C(C)OCC | null | 0.5 | CCC=O.CCCNc1c(SC)nn2c(-c3ccc(Cl)cc3Cl)cccc12>O.O1CCCC1.C(C)OCC>CCCN(CCC)c1c(SC)nn2c(-c3ccc(Cl)cc3Cl)cccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-da5cc28d52f34a9bb0dac4ca84cbc6ef | COc1cc(C)cc(C)c1-c1cccc2c(NCC3CC3)c(SC)nn12.O=CC1CCOCC1>>COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CCOCC3)CC3CC3)c(SC)nn12 | C(O)([O-])=O.[Na+].C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].C1(CC1)CNC=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)SC.O1CCC(CC1)C=O>>C1(CC1)CN(CC1CCOCC1)C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)SC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]([NH:17][CH2:25][CH:26]3[CH2:27][CH2:28]3)[c:29]([S:30][CH3:31])[n:32][n:33]12.O=[CH:18][CH:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH... | COc1cc(C)cc(C)c1-c1cccc2c(NCC3CC3)c(SC)nn12.O=CC1CCOCC1 | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CCOCC3)CC3CC3)c(SC)nn12 | null | null | C(C)(=O)OCC.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 6d9c60e7c47e75322fc9565d992b855788f3516a27cb14d7f9ed299e190b30d3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(-c2cccc3c(N(CC4CCOCC4)CC4CC4)cnn23)cc1 | O=[CH;D2;+0:1]-[C:2](-[C:3])-[C:4].[#16:5]-[c:6]1:[#7;a:7]:[#7;a:8](:[c:9]):[c:10](:[c:11]):[c:12]:1-[NH;D2;+0:13]-[C:14]-[C:15]>>[#16:5]-[c:6]1:[#7;a:7]:[#7;a:8](:[c:9]):[c:10](:[c:11]):[c:12]:1-[N;H0;D3;+0:13](-[C:14]-[C:15])-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4] | 55.2 | [{"value": 55.2, "product": "C1(CC1)CN(CC1CCOCC1)C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | After dissolving N-cyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine (100 mg) in tetrahydrofuran (2 mL), tetrahydro-2H-4-pyrancarbaldehyde (78 mg) [CAS No. 50675-18-8] and sodium triacetoxyborohydride (87 mg) were added, and the mixture was stirred for 1 hour. Sat... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | null | null | c1ccccc1.C1CCOCC1.C1CC1.c1ccn2nccc2c1 | Other | C(C)(=O)OCC.O1CCCC1 | null | 1 | COc1cc(C)cc(C)c1-c1cccc2c(NCC3CC3)c(SC)nn12.O=CC1CCOCC1>C(C)(=O)OCC.O1CCCC1>COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CCOCC3)CC3CC3)c(SC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-913505a067b447da97fdb3eb4c2cf794 | COc1cc(C)cc(C)c1-c1cccc2c(NC(=O)OC(C)(C)C)c(SC)nn12.Cc1ccc(S(=O)(=O)OCC2CCO2)cc1>>COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CCO3)C(=O)OC(C)(C)C)c(SC)nn12 | CC1=CC=C(C=C1)S(=O)(=O)OCC1OCC1.O.COC1=C(C(=CC(=C1)C)C)C1=CC=CC=2N1N=C(C2NC(OC(C)(C)C)=O)SC.[H-].[Na+].[H-].[Na+].CC1=CC=C(C=C1)S(=O)(=O)OCC1OCC1>>COC1=C(C(=CC(=C1)C)C)C1=CC=CC=2N1N=C(C2N(C(OC(C)(C)C)=O)CC2OCC2)SC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]([NH:17][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[c:30]([S:31][CH3:32])[n:33][n:34]12.Cc1ccc(S(=O)(=O)O[CH2:18][CH:19]2[CH2:20][CH2:21][O:22]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8](... | COc1cc(C)cc(C)c1-c1cccc2c(NC(=O)OC(C)(C)C)c(SC)nn12.Cc1ccc(S(=O)(=O)OCC2CCO2)cc1 | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CCO3)C(=O)OC(C)(C)C)c(SC)nn12 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 06f01055eff894977eb696659764925ee324ab8b67c8917afae1d1a679aeeba8 | 0ad5e99f176c150355cbf68e0a10d4d18618ad9c86a6bf4c7c4407d9cc055d92 | c1ccc(-c2cccc3c(NCC4CCO4)cnn23)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4]-[C:5]-2):c:c:1.[#16:6]-[c:7]1:[#7;a:8]:[#7;a:9](:[c:10]):[c:11](:[c:12]):[c:13]:1-[NH;D2;+0:14]-[C:15](=[O;D1;H0:16])-[#8:17]-[C:18](-[C;D1;H3:19])(-[C;D1;H3:20])-[C;D1;H3:21]>>[#16:6]-[c:7]1:[#7;a:8]:[#7;a:9](:[c:10]):[c:11](:[c:12]):[c:13]:1-[N;H0;D3;+0:14](-[... | null | [] | null | null | 30 | MINUTE | After dissolving tert-butyl N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate (100 mg) in N,N-dimethylformamide (2 mL), sodium hydride (60%, 15 mg) was added while cooling on ice, the mixture was stirred for 30 minutes, 2-oxetanylmethyl 4-methyl-1-benzenesulfonate (70 mg) was a... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Carbamic ester | Carbamic ester | c1ccccc1 | null | c1ccccc1.C1COC1.c1ccn2nccc2c1 | TsOH.HO- | CN(C=O)C.C(C)(=O)OCC | null | 0.5 | COc1cc(C)cc(C)c1-c1cccc2c(NC(=O)OC(C)(C)C)c(SC)nn12.Cc1ccc(S(=O)(=O)OCC2CCO2)cc1>CN(C=O)C.C(C)(=O)OCC>COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CCO3)C(=O)OC(C)(C)C)c(SC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c46a2b2bab70456c9f3e8f570d3e7f62 | BrCC1CC1.COc1cc(C)cc(C)c1-c1cccc2c(NCC3CCO3)c(SC)nn12>>COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CCO3)c(SC)nn12 | O.C1(CC1)CBr.COC1=C(C(=CC(=C1)C)C)C1=CC=CC=2N1N=C(C2NCC2OCC2)SC.[H-].[Na+]>>C1(CC1)CN(CC1OCC1)C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)SC | Br[CH2:18][CH:19]1[CH2:20][CH2:21]1.[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]([NH:17][CH2:22][CH:23]3[CH2:24][CH2:25][O:26]3)[c:27]([S:28][CH3:29])[n:30][n:31]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:... | BrCC1CC1.COc1cc(C)cc(C)c1-c1cccc2c(NCC3CCO3)c(SC)nn12 | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CCO3)c(SC)nn12 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2cccc3c(N(CC4CC4)CC4CCO4)cnn23)cc1 | Br-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[#16:5]-[c:6]1:[#7;a:7]:[#7;a:8](:[c:9]):[c:10](:[c:11]):[c:12]:1-[NH;D2;+0:13]-[C:14]-[C:15]-[#8:16]>>[#16:5]-[c:6]1:[#7;a:7]:[#7;a:8](:[c:9]):[c:10](:[c:11]):[c:12]:1-[N;H0;D3;+0:13](-[C:14]-[C:15]-[#8:16])-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1 | null | [] | null | null | 12 | HOUR | After dissolving N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(2-oxetanylmethyl)amine (8 mg) in N,N-dimethylformamide (2 mL), sodium hydride (60%, 1.6 mg) was added while cooling on ice, and then cyclopropylmethyl bromide (3.8 μL) was added and the mixture was stirred at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.C1CC1.C1COC1.c1ccn2nccc2c1 | HBr | CN(C=O)C.C(C)(=O)OCC | null | 12 | BrCC1CC1.COc1cc(C)cc(C)c1-c1cccc2c(NCC3CCO3)c(SC)nn12>CN(C=O)C.C(C)(=O)OCC>COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CCO3)c(SC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f5c71bbf9f444b2692fe5173af016392 | C1CCOC1.COc1cc(C)cc(C)c1-c1cccc2c(NCC(C)OC(=O)c3ccccc3)c(SC)nn12>>COc1cc(C)cc(C)c1-c1cccc2c(NC(CC3CC3)C(C)O)c(SC)nn12 | [OH-].[Na+].S(O)(O)(=O)=O.C(C1=CC=CC=C1)(=O)OC(CNC=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)SC)C.O1CCCC1.[BH4-].[Na+]>>C1(CC1)CC(C(C)O)NC=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)SC | O1[CH2:19][CH2:20][CH2:21][CH2:22]1.O=C(c1ccccc1)[O:25][CH:23]([CH2:18][NH:17][c:16]1[c:15]2[cH:14][cH:13][cH:12][c:11](-[c:10]3[c:3]([O:2][CH3:1])[cH:4][c:5]([CH3:6])[cH:7][c:8]3[CH3:9])[n:30]2[n:29][c:26]1[S:27][CH3:28])[CH3:24]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][... | C1CCOC1.COc1cc(C)cc(C)c1-c1cccc2c(NCC(C)OC(=O)c3ccccc3)c(SC)nn12 | COc1cc(C)cc(C)c1-c1cccc2c(NC(CC3CC3)C(C)O)c(SC)nn12 | null | null | CO | C-C Coupling | OtherReaction | b94617f8cc97f0f6ad6b68ab8fdab0d84cbb8129539356a79030280a0a3f54a5 | ef48126ecdbc5cf772d16ea093bb244a788351fa21d111f53bb3935584423ba7 | c1ccc(-c2cccc3c(NCCC4CC4)cnn23)cc1 | O1-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C:3]-[CH2;D2;+0:4]-1.O=C(-[O;H0;D2;+0:5]-[C:6](-[C;D1;H3:7])-[CH2;D2;+0:8]-[#7:9]-[c:10]1:[c:11]:[#7;a:12]:[#7;a:13]:[c:14]:1)-c1:c:c:c:c:c:1>>[C;D1;H3:7]-[C:6](-[OH;D1;+0:5])-[CH;D3;+0:8](-[#7:9]-[c:10]1:[c:11]:[#7;a:12]:[#7;a:13]:[c:14]:1)-[CH2;D2;+0:1]-[CH;D3;+0:2]1-[C:3]-[CH2;D2;+0:4... | null | [] | null | null | 30 | MINUTE | Cyclopropanecarboxyaldehyde (0.047 mL) and 3 M sulfuric acid (0.21 mL) were added to a solution of 2-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amino-1-methylethyl benzoate (100 mg) in tetrahydrofuran (0.7 mL) while cooling on ice, and then sodium borohydride (16 mg) was slowly adde... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Secondary alcohol | C1CCOC1.c1ccccc1 | C1CC1 | c1ccccc1.C1CC1.c1ccn2nccc2c1 | HO- | CO | null | 0.5 | C1CCOC1.COc1cc(C)cc(C)c1-c1cccc2c(NCC(C)OC(=O)c3ccccc3)c(SC)nn12>CO>COc1cc(C)cc(C)c1-c1cccc2c(NC(CC3CC3)C(C)O)c(SC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9937cf80a3b14089a39c068e340e6f8e | COc1cc(C)cc(C)c1-c1cccc2c(NCC3CC3)c(SC)nn12.FCC1CO1>>COc1cc(C)cc(C)c1-c1cccc2c(NC(CC3CC3)C(O)CF)c(SC)nn12 | O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(F)C1CO1.C1(CC1)CNC=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)SC>>C1(CC1)CC(C(CF)O)NC=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)SC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]([NH:17][CH2:19][CH:20]3[CH2:21][CH2:22]3)[c:27]([S:28][CH3:29])[n:30][n:31]12.[CH2:18]1[CH:23]([CH2:25][F:26])[O:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:14... | COc1cc(C)cc(C)c1-c1cccc2c(NCC3CC3)c(SC)nn12.FCC1CO1 | COc1cc(C)cc(C)c1-c1cccc2c(NC(CC3CC3)C(O)CF)c(SC)nn12 | null | null | COCCOC | Heteroatom Alkylation and Arylation | OtherReaction | fda499d57f6b50af5f938aa2225714ba9c706cee24a0860e722578d35bd8f218 | 44f0f98267935086e7e06becbfd88bd9220317f0f521b960be901561fa43c70b | c1ccc(-c2cccc3c(NCCC4CC4)cnn23)cc1 | [#16:1]-[c:2]1:[#7;a:3]:[#7;a:4](:[c:5]):[c:6](:[c:7]):[c:8]:1-[NH;D2;+0:9]-[CH2;D2;+0:10]-[C:11]1-[C:12]-[C:13]-1.[C:14]-[C:15]1-[CH2;D2;+0:16]-[O;H0;D2;+0:17]-1>>[#16:1]-[c:2]1:[#7;a:3]:[#7;a:4](:[c:5]):[c:6](:[c:7]):[c:8]:1-[NH;D2;+0:9]-[CH;D3;+0:16](-[CH2;D2;+0:10]-[C:11]1-[C:12]-[C:13]-1)-[C:15](-[C:14])-[OH;D1;+0... | null | [] | null | null | null | null | p-Toluenesulfonic acid hydrate (40 mg) and epifluorohydrin (0.15 mL) [CAS No.503-09-3] were added to a solution of N-cyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine (50 mg) in 1,2-dimethoxyethane (0.40 mL), and the mixture was heated to reflux for 3 hours. After... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Secondary amine | C1CO1 | null | c1ccccc1.C1CC1.c1ccn2nccc2c1 | null | COCCOC | null | null | COc1cc(C)cc(C)c1-c1cccc2c(NCC3CC3)c(SC)nn12.FCC1CO1>COCCOC>COc1cc(C)cc(C)c1-c1cccc2c(NC(CC3CC3)C(O)CF)c(SC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-47a5528724e2431dbb12cb455458e194 | COc1cc(Br)ccc1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12>>COc1cc(C#N)ccc1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12 | BrC1=CC(=C(C=C1)C1=CC=CC=2N1N=C(C2N(CC2CC2)CC2CC2)SC)OC.CN(C=O)C.C(C)(=O)OCC>>C1(CC1)CN(C=1C(=NN2C1C=CC=C2C2=C(C=C(C#N)C=C2)OC)SC)CC2CC2 | Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]3[c:16]([N:17]([CH2:18][CH:19]4[CH2:20][CH2:21]4)[CH2:22][CH:23]4[CH2:24][CH2:25]4)[c:26]([S:27][CH3:28])[n:29][n:30]23)[cH:9][cH:8]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]#[N:7])[cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]([N:17]... | COc1cc(Br)ccc1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12 | COc1cc(C#N)ccc1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12 | null | [C-]#N.[Zn+2].[C-]#N | null | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccc(-c2cccc3c(N(CC4CC4)CC4CC4)cnn23)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[N;D1;H0:6]#[C:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 95 | CELSIUS | 12 | HOUR | After dissolving N-[7-(4-bromo-2-methoxyphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N,N-dicyclopropylmethylamine (60 mg) in N,N-dimethylformamide (0.26 mL), zinc cyanide (31 mg) and tetrakis (triphenylphosphine)palladium (0) complex (23 mg) were added, the mixture was heated and stirred at 95° C. for 12 hour... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC1.C1CC1.c1ccn2nccc2c1 | Br- | [C-]#N.[Zn+2].[C-]#N | 95 | 12 | COc1cc(Br)ccc1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12>[C-]#N.[Zn+2].[C-]#N>COc1cc(C#N)ccc1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1d28720315fc4f67a65cac0df851c4fc | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nccs1.COc1cc(Br)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12>>COc1cc(-c2nccs2)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12 | C(C)(=O)OCC.BrC1=CC(=C(C(=C1)C)C1=CC=CC=2N1N=C(C2N(CC2CC2)CC2CC2)SC)OC.C(CCC)[Sn](CCCC)(CCCC)C=1SC=CN1>>C1(CC1)CN(C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C=2SC=CN2)OC)SC)CC2CC2 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:6]1[n:7][cH:8][cH:9][s:10]1.Br[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:14](-[c:15]2[cH:16][cH:17][cH:18][c:19]3[c:20]([N:21]([CH2:22][CH:23]4[CH2:24][CH2:25]4)[CH2:26][CH:27]4[CH2:28][CH2:29]4)[c:30]([S:31][CH3:32])[n:33][n:34]23)[c:12]([CH3:13])[cH:11]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nccs1.COc1cc(Br)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12 | COc1cc(-c2nccs2)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12 | null | null | C1(=CC=CC=C1)C | C-C Coupling | Stille reaction_aryl | 11853d887eacc5b6acaefa13bd61251ef8f10709d6f24dc2d2a7d5e65c01de84 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1cc(-c2ccc(-c3nccs3)cc2)n2ncc(N(CC3CC3)CC3CC3)c2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1):[c:4]:[c:5] | 66.1 | [{"value": 66.1, "product": "C1(CC1)CN(C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C=2SC=CN2)OC)SC)CC2CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 2 | HOUR | After dissolving N-[7-(4-bromo-2-methoxy-6-methylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N,N-dicyclopropylmethylamine (45 mg) in toluene (0.60 mL), tributylstannylthiazole (52 mg) and tetrakis (triphenylphosphine)palladium (0) complex (9 mg) were added, the mixture was heated and stirred at 120° C. for 2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1cscn1.c1ccccc1 | c1ccccc1.c1cscn1 | c1ccccc1.c1cscn1.C1CC1.C1CC1.c1ccn2nccc2c1 | HBr.Sn | C1(=CC=CC=C1)C | 120 | 2 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nccs1.COc1cc(Br)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12>C1(=CC=CC=C1)C>COc1cc(-c2nccs2)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c733e954d17546e38092c836e263de83 | COc1cc(C)cc(C)c1-c1cccc2c(N(Cc3cccnc3OC)CC3CC3)c(SC)nn12>>COc1cc(C)cc(C)c1-c1cccc2c(NC(CC3CC3)c3cccnc3O)c(SC)nn12 | C(C)(=O)OCC.Cl.C(C)(=O)OCC.C1(CC1)CN(CC=1C(=NC=CC1)OC)C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)SC.C(O)([O-])=O.[Na+]>>C1(CC1)CC(C=1C(=NC=CC1)O)NC=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)SC | C[O:29][c:28]1[c:23]([CH2:18][N:17]([c:16]2[c:15]3[cH:14][cH:13][cH:12][c:11](-[c:10]4[c:3]([O:2][CH3:1])[cH:4][c:5]([CH3:6])[cH:7][c:8]4[CH3:9])[n:34]3[n:33][c:30]2[S:31][CH3:32])[CH2:19][CH:20]2[CH2:21][CH2:22]2)[cH:24][cH:25][cH:26][n:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH... | COc1cc(C)cc(C)c1-c1cccc2c(N(Cc3cccnc3OC)CC3CC3)c(SC)nn12 | COc1cc(C)cc(C)c1-c1cccc2c(NC(CC3CC3)c3cccnc3O)c(SC)nn12 | null | null | C(C)O | Miscellaneous | OtherReaction | 9660de0bb5f9f195c92f14621d75a61c29f6ba87ee4fab2c1992d94e74b6efb6 | 36d9f4bbb17f2f5f5fa17b7330992c2884d73646e1c559d6cf2ea48b72773382 | c1ccc(-c2cccc3c(NC(CC4CC4)c4cccnc4)cnn23)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[CH2;D2;+0:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:8]-[C:9]1-[C:10]-[C:11]-1)-[c:12]1:[c:13](:[c:14]):[#7;a:15](:[c:16]):[#7;a:17]:[c:18]:1-[#16:19]):[c:20]>>[#16:19]-[c:18]1:[#7;a:17]:[#7;a:15](:[c:16]):[c:13](:[c:14]):[c:12]:1-[NH;D2;+0:7]-[CH;D3;+0:6](-[CH2;D2;+0:8]-[C:9]1-[C:10]... | null | [] | null | null | null | null | After dissolving N-cyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]-N-[(2-methoxy-3-pyridyl)methyl]amine (63 mg) in ethanol (1 mL), a 4 N hydrochloric acid/ethyl acetate solution (1 mL) was added at room temperature and the mixture was heated to reflux for 3 hours. Sa... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amine | Aromatic alcohol.Secondary amine | null | null | c1ccccc1.C1CC1.c1ccncc1.c1ccn2nccc2c1 | Other | C(C)O | null | null | COc1cc(C)cc(C)c1-c1cccc2c(N(Cc3cccnc3OC)CC3CC3)c(SC)nn12>C(C)O>COc1cc(C)cc(C)c1-c1cccc2c(NC(CC3CC3)c3cccnc3O)c(SC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7700df5685184235ac02c3c0c47a1faa | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12>>CSc1nn2c(-c3c(C)cc(C)cc3O)cccc2c1N(CC1CC1)CC1CC1 | C(C)(=O)OCC.B(Br)(Br)Br.ClCCl.C1(CC1)CN(C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)SC)CC2CC2>>C1(CC1)CN(C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)O)SC)CC2CC2 | C[O:15][c:14]1[c:7](-[c:6]2[n:5]3[n:4][c:3]([S:2][CH3:1])[c:20]([N:21]([CH2:22][CH:23]4[CH2:24][CH2:25]4)[CH2:26][CH:27]4[CH2:28][CH2:29]4)[c:19]3[cH:18][cH:17][cH:16]2)[c:8]([CH3:9])[cH:10][c:11]([CH3:12])[cH:13]1>>[CH3:1][S:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[c:8]([CH3:9])[cH:10][c:11]([CH3:12])[cH:13][c:14]3[OH:15])[cH... | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12 | CSc1nn2c(-c3c(C)cc(C)cc3O)cccc2c1N(CC1CC1)CC1CC1 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2cccc3c(N(CC4CC4)CC4CC4)cnn23)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 50.2 | [{"value": 50.2, "product": "C1(CC1)CN(C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)O)SC)CC2CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A 1 M boron tribromide/dichloromethane solution (0.42 mL) was added to a solution of N,N-dicyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine (35 mg) in dichloromethane (10 mL) at room temperature under a nitrogen atmosphere, and the mixture was stirred for 10 minu... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccn2nccc2c1.C1CC1.C1CC1 | Other | ClCCl | null | 0.166667 | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12>ClCCl>CSc1nn2c(-c3c(C)cc(C)cc3O)cccc2c1N(CC1CC1)CC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9482f3b28cc4406ca403d81c37c7da8b | CCO.CSc1nn2c(-c3c(C)cc(C)cc3O)cccc2c1N(CC1CC1)CC1CC1>>CCOc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12 | C(C)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=NC(=O)OCC)C(=O)OCC.C1(CC1)CN(C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)O)SC)CC2CC2>>C1(CC1)CN(C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OCC)SC)CC2CC2 | O[CH2:2][CH3:1].[OH:3][c:4]1[cH:5][c:6]([CH3:7])[cH:8][c:9]([CH3:10])[c:11]1-[c:12]1[cH:13][cH:14][cH:15][c:16]2[c:17]([N:18]([CH2:19][CH:20]3[CH2:21][CH2:22]3)[CH2:23][CH:24]3[CH2:25][CH2:26]3)[c:27]([S:28][CH3:29])[n:30][n:31]12>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([CH3:7])[cH:8][c:9]([CH3:10])[c:11]1-[c:12]1[cH:13]... | CCO.CSc1nn2c(-c3c(C)cc(C)cc3O)cccc2c1N(CC1CC1)CC1CC1 | CCOc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12 | null | null | O.C(C)(=O)OCC.O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(-c2cccc3c(N(CC4CC4)CC4CC4)cnn23)cc1 | O-[CH2;D2;+0:1]-[C;D1;H3:2].[OH;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | 8 | HOUR | After adding ethanol (2 μL), triphenylphosphine (15 mg) and diethyl azodicarboxylate (9 μL) to a solution of 2-[3-[di(cyclopropylmethyl)amino]-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-7-yl]-3,5-dimethylphenol (15 mg) in tetrahydrofuran (0.45 mL) under a nitrogen atmosphere, the mixture was stirred at room temperature o... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CC1.C1CC1.c1ccn2nccc2c1 | HO- | O.C(C)(=O)OCC.O1CCCC1 | null | 8 | CCO.CSc1nn2c(-c3c(C)cc(C)cc3O)cccc2c1N(CC1CC1)CC1CC1>O.C(C)(=O)OCC.O1CCCC1>CCOc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-12b9d93cbaf540ff86cb12bccf40743c | CCOC1(O[Si](C)(C)C)CC1.COc1cc(C)cc(C)c1-c1cccc2c(NCC3CC3)c(SC)nn12>>COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)C3CC3)c(SC)nn12 | C1(CC1)CNC=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)SC.C(#N)[BH3-].[Na+].C(C)OC1(CC1)O[Si](C)(C)C.C(O)([O-])=O.[Na+]>>C1(CC1)N(C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)SC)CC2CC2 | CCO[C:22]1(O[Si](C)(C)C)[CH2:23][CH2:24]1.[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]([NH:17][CH2:18][CH:19]3[CH2:20][CH2:21]3)[c:25]([S:26][CH3:27])[n:28][n:29]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:... | CCOC1(O[Si](C)(C)C)CC1.COc1cc(C)cc(C)c1-c1cccc2c(NCC3CC3)c(SC)nn12 | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)C3CC3)c(SC)nn12 | null | null | CO.C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 1cd2925629819ee9966013ee23bd33624f46250d5e16eba4b07f5b29b953c5db | d68204a4cfa34cff6cd0e9ec3beba0b05875e761733cc428bd8f8c7f1d92fb07 | c1ccc(-c2cccc3c(N(CC4CC4)C4CC4)cnn23)cc1 | C-C-O-[C;H0;D4;+0:1]1(-O-[Si](-C)(-C)-C)-[C:2]-[C:3]-1.[#16:4]-[c:5]1:[#7;a:6]:[#7;a:7](:[c:8]):[c:9](:[c:10]):[c:11]:1-[NH;D2;+0:12]-[C:13]-[C:14]>>[#16:4]-[c:5]1:[#7;a:6]:[#7;a:7](:[c:8]):[c:9](:[c:10]):[c:11]:1-[N;H0;D3;+0:12](-[C:13]-[C:14])-[CH;D3;+0:1]1-[C:2]-[C:3]-1 | null | [] | null | null | null | null | After dissolving N-cyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine (100 mg) in methanol (10 mL), ((1-ethoxycyclopropyl)oxy)trimethylsilane (60 μL), acetic acid (298 μL) and sodium cyanoborohydride (171 mg) were added and the mixture was heated to reflux for 6 ho... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine.Silyl protective group | Tertiary amine | C1CC1 | C1CC1 | c1ccccc1.C1CC1.C1CC1.c1ccn2nccc2c1 | HO- | CO.C(C)(=O)O | null | null | CCOC1(O[Si](C)(C)C)CC1.COc1cc(C)cc(C)c1-c1cccc2c(NCC3CC3)c(SC)nn12>CO.C(C)(=O)O>COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)C3CC3)c(SC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1041e44b85e54e55bc7caa4f4b544baa | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12.O=C(OO)c1cccc(Cl)c1>>COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(S(C)=O)nn12 | C(C)(=O)OCC.ClC1=CC(=CC=C1)C(=O)OO.C1(CC1)CN(C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)SC)CC2CC2.O>>C1(CC1)CN(C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)S(=O)C)CC2CC2 | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]([N:17]([CH2:18][CH:19]3[CH2:20][CH2:21]3)[CH2:22][CH:23]3[CH2:24][CH2:25]3)[c:26]([S:27][CH3:28])[n:30][n:31]12.O=C(O[OH:29])c1cccc(Cl)c1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1... | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12.O=C(OO)c1cccc(Cl)c1 | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(S(C)=O)nn12 | null | null | ClCCl | Oxidation | Sulfanyl to sulfinyl_peroxide | 95b5106b07a173d8eafc1c9c8a6c938befe131c3d1caaf5886529b7aee55ea9d | 7652b53bb02130dccfe4b1e8905d7f3db7f05ff3a95a0003c1bab09b1ad4083e | c1ccc(-c2cccc3c(N(CC4CC4)CC4CC4)cnn23)cc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C;D1;H3:2]-[S;H0;D2;+0:3]-[c:4]1:[#7;a:5]:[#7;a:6](:[c:7]):[c:8]:[c:9]:1>>[C;D1;H3:2]-[S;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4]1:[#7;a:5]:[#7;a:6](:[c:7]):[c:8]:[c:9]:1 | 78 | [{"value": 78.0, "product": "C1(CC1)CN(C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)S(=O)C)CC2CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | m-Chloroperbenzoic acid (234 mg) was added to a solution of N,N-dicyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine (200 mg) in dichloromethane (10 mL) at 0° C., and the mixture was stirred for 2 hours. Water was added to the reaction mixture, extraction was perfo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfoxide | c1ccccc1 | null | c1ccccc1.C1CC1.C1CC1.c1ccn2nccc2c1 | HCl | ClCCl | null | 2 | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(SC)nn12.O=C(OO)c1cccc(Cl)c1>ClCCl>COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(S(C)=O)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0073396e34064309a3a1966475a4eabd | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(S(C)=O)nn12.O=C(OO)c1cccc(Cl)c1>>COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(S(C)(=O)=O)nn12 | C(C)(=O)OCC.ClC1=CC(=CC=C1)C(=O)OO.C1(CC1)CN(C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)S(=O)C)CC2CC2.O>>C1(CC1)CN(C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)S(=O)(=O)C)CC2CC2 | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]([N:17]([CH2:18][CH:19]3[CH2:20][CH2:21]3)[CH2:22][CH:23]3[CH2:24][CH2:25]3)[c:26]([S:27]([CH3:28])=[O:30])[n:31][n:32]12.OOC(c1cccc(Cl)c1)=[O:29]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1... | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(S(C)=O)nn12.O=C(OO)c1cccc(Cl)c1 | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(S(C)(=O)=O)nn12 | null | null | ClCCl | Oxidation | OtherReaction | acb5ca4c8f7333436ad9c46402b4d8d39ad383b29b18f83703b13602938a2ed3 | 5b256bc2e56a358558754dd634ffe9096ff47f39d0e6c3a4cca49ae176a9ce2c | c1ccc(-c2cccc3c(N(CC4CC4)CC4CC4)cnn23)cc1 | Cl-c1:c:c:c:c(-C(=[O;H0;D1;+0:1])-O-O):c:1.[C;D1;H3:2]-[S;H0;D3;+0:3](=[O;D1;H0:4])-[c:5]1:[#7;a:6]:[#7;a:7](:[c:8]):[c:9]:[c:10]:1>>[C;D1;H3:2]-[S;H0;D4;+0:3](=[O;D1;H0:4])(=[O;H0;D1;+0:1])-[c:5]1:[#7;a:6]:[#7;a:7](:[c:8]):[c:9]:[c:10]:1 | 5.4 | [{"value": 5.4, "product": "C1(CC1)CN(C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)S(=O)(=O)C)CC2CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | m-Chloroperbenzoic acid (91 mg) was added to a solution of N,N-dicyclopropylmethyl-N-[7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfinyl)pyrazolo[1,5-a]pyridin-3-yl]amine (162 mg) in dichloromethane (10 mL) at 0° C., and the mixture was stirred for 4 hours. Water was added to the reaction mixture, extraction was perfor... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Sulfoxide | Sulfone | c1ccccc1 | null | c1ccccc1.C1CC1.C1CC1.c1ccn2nccc2c1 | HCl | ClCCl | null | 4 | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(S(C)=O)nn12.O=C(OO)c1cccc(Cl)c1>ClCCl>COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CC3)CC3CC3)c(S(C)(=O)=O)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7ecab425a26b4e54a2d30fc679202989 | COc1cc(C)cc(C)c1-c1cccc2c(N=O)c(OC)nn12>>COc1cc(C)cc(C)c1-c1cccc2c(N)c(OC)nn12 | O.C(C)(=O)O.COC1=NN2C(C=CC=C2C2=C(C=C(C=C2C)C)OC)=C1N=O>>COC1=NN2C(C=CC=C2C2=C(C=C(C=C2C)C)OC)=C1N | O=[N:17][c:16]1[c:15]2[cH:14][cH:13][cH:12][c:11](-[c:10]3[c:3]([O:2][CH3:1])[cH:4][c:5]([CH3:6])[cH:7][c:8]3[CH3:9])[n:22]2[n:21][c:18]1[O:19][CH3:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]([NH2:17])[c:18]([O:19][CH3:20])[n:21][n:22]12 | COc1cc(C)cc(C)c1-c1cccc2c(N=O)c(OC)nn12 | COc1cc(C)cc(C)c1-c1cccc2c(N)c(OC)nn12 | null | [Zn] | C(C)O | Reduction | OtherReaction | 10bd501bc4fc8c6849398545fc18bd5f6b51ea4e37b15a00157d17550a6b88bf | 7085a0cec3cc6daaf2fab855d070c407558563b5b6837070687c0df0a552c6fe | c1ccc(-c2cccc3ccnn23)cc1 | O=[N;H0;D2;+0:1]-[c:2]1:[c:3](:[c:4]):[#7;a:5](:[c:6]):[#7;a:7]:[c:8]:1-[#8:9]>>[#8:9]-[c:8]1:[#7;a:7]:[#7;a:5](:[c:6]):[c:3](:[c:4]):[c:2]:1-[NH2;D1;+0:1] | null | [] | 60 | CELSIUS | 1 | HOUR | 2-Methoxy-7-(2-methoxy-4,6-dimethylphenyl)-3-nitrosopyrazolo[1,5-a]pyridine (200 mg) was suspended in ethanol (10 mL), and then water (5 mL), acetic acid (0.5 mL) and zinc powder (200 mg) were added and the mixture was heated and stirred at 60° C. for 1 hour. The reaction mixture was filtered, water was added to the fi... | 10.6084/m9.figshare.5104873.v1 | null | Nitroso | Primary amine | null | null | c1ccccc1.c1ccn2nccc2c1 | Other | [Zn].C(C)O | 60 | 1 | COc1cc(C)cc(C)c1-c1cccc2c(N=O)c(OC)nn12>[Zn].C(C)O>COc1cc(C)cc(C)c1-c1cccc2c(N)c(OC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-86b007e3ac12424397c9f7c9e7aff08f | COc1cc(C)c(OB(O)O)c(OC)c1.COc1nn2c(Br)cccc2c1NC(=O)OC(C)(C)C>>COc1cc(C)c(-c2cccc3c(NC(=O)OC(C)(C)C)c(OC)nn23)c(OC)c1 | BrC1=CC=CC=2N1N=C(C2NC(OC(C)(C)C)=O)OC.CC1=CC(=CC(=C1OB(O)O)OC)OC.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C(C)(=O)OCC>>COC1=C(C(=CC(=C1)OC)C)C1=CC=CC=2N1N=C(C2NC(OC(C)(C)C)=O)OC | OB(O)O[c:7]1[c:5]([CH3:6])[cH:4][c:3]([O:2][CH3:1])[cH:30][c:27]1[O:28][CH3:29].Br[c:8]1[cH:9][cH:10][cH:11][c:12]2[c:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[c:22]([O:23][CH3:24])[n:25][n:26]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[c:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]3[c:13]([NH:14][C:15... | COc1cc(C)c(OB(O)O)c(OC)c1.COc1nn2c(Br)cccc2c1NC(=O)OC(C)(C)C | COc1cc(C)c(-c2cccc3c(NC(=O)OC(C)(C)C)c(OC)nn23)c(OC)c1 | null | null | O.COCCOC | C-C Coupling | OtherReaction | 8b93332ffb86325cf5e747a3ea9faae13848b7451cf269888446bfaf73495994 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2cccc3ccnn23)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[#7;a:4](:[c:5]):[#7;a:6]:[c:7].O-B(-O)-O-[c;H0;D3;+0:8](:[c:9](-[#8:10]):[c:11]):[c:12](-[C;D1;H3:13]):[c:14]>>[#8:10]-[c:9](:[c:11]):[c;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[#7;a:4](:[c:5]):[#7;a:6]:[c:7]):[c:12](-[C;D1;H3:13]):[c:14] | 63.4 | [{"value": 63.4, "product": "COC1=C(C(=CC(=C1)OC)C)C1=CC=CC=2N1N=C(C2NC(OC(C)(C)C)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 3 | HOUR | After dissolving tert-butyl N-(7-bromo-2-methoxypyrazolo[1,5-a]pyridin-3-yl)carbamate (300 mg) in 1,2-dimethoxyethane (10 mL) and water (5 mL), 6-methyl-2,4-dimethoxyphenylboric acid (258 mg), tetrakis (triphenylphosphine)palladium (0) complex (203 mg) and barium hydroxide octahydrate (415 mg) were added and the mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1ccn2nccc2c1 | c1ccccc1.c1ccn2nccc2c1 | c1ccccc1.c1ccn2nccc2c1 | HBr.B | O.COCCOC | 80 | 3 | COc1cc(C)c(OB(O)O)c(OC)c1.COc1nn2c(Br)cccc2c1NC(=O)OC(C)(C)C>O.COCCOC>COc1cc(C)c(-c2cccc3c(NC(=O)OC(C)(C)C)c(OC)nn23)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a82f111339944dda3d2ac4aa6d1ffa2 | COc1cc(C)c(-c2cccc3c(NC(=O)OC(C)(C)C)c(OC)nn23)c(OC)c1.ClCC1CCCO1>>COc1cc(C)c(-c2cccc3c(N(CC4CCCO4)C(=O)OC(C)(C)C)c(OC)nn23)c(OC)c1 | O.O1C(CCC1)CCl.COC1=C(C(=CC(=C1)OC)C)C1=CC=CC=2N1N=C(C2NC(OC(C)(C)C)=O)OC.[H-].[Na+]>>COC1=C(C(=CC(=C1)OC)C)C1=CC=CC=2N1N=C(C2N(C(OC(C)(C)C)=O)CC2OCCC2)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[c:7](-[c:8]2[cH:9][cH:10][cH:11][c:12]3[c:13]([NH:14][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[c:28]([O:29][CH3:30])[n:31][n:32]23)[c:33]([O:34][CH3:35])[cH:36]1.Cl[CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][O:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[c:7](-[c:8]2[c... | COc1cc(C)c(-c2cccc3c(NC(=O)OC(C)(C)C)c(OC)nn23)c(OC)c1.ClCC1CCCO1 | COc1cc(C)c(-c2cccc3c(N(CC4CCCO4)C(=O)OC(C)(C)C)c(OC)nn23)c(OC)c1 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 5da873da5e065666521679df8db5a1d2754540edd93ae40997847c9a24dedeb3 | c05cd517c346aa4e8e8e58218c491edaea33d354b5dba9eb90dac8ad97104f73 | c1ccc(-c2cccc3c(NCC4CCCO4)cnn23)cc1 | Cl-[CH2;D2;+0:1]-[C:2](-[C:3])-[#8:4]-[C:5].[#8:6]-[c:7]1:[#7;a:8]:[#7;a:9](:[c:10]):[c:11](:[c:12]):[c:13]:1-[NH;D2;+0:14]-[C:15](=[O;D1;H0:16])-[#8:17]-[C:18](-[C;D1;H3:19])(-[C;D1;H3:20])-[C;D1;H3:21]>>[#8:6]-[c:7]1:[#7;a:8]:[#7;a:9](:[c:10]):[c:11](:[c:12]):[c:13]:1-[N;H0;D3;+0:14](-[CH2;D2;+0:1]-[C:2](-[C:3])-[#8:... | null | [] | 60 | CELSIUS | 3 | HOUR | After dissolving tert-butyl N-[7-(2,4-dimethoxy-6-methylphenyl)-2-methoxypyrazolo[1,5-a]pyridin-3-yl]carbamate (50 mg) in N,N-dimethylformamide (2 mL), sodium hydride (60%, 15 mg) was added while cooling on ice, and then 2-tetrahydrofuranylmethyl chloride (16 μL) was added and the mixture was stirred for 3 hours at 60°... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester | Carbamic ester | null | null | c1ccccc1.C1CCOC1.c1ccn2nccc2c1 | HCl | CN(C=O)C.C(C)(=O)OCC | 60 | 3 | COc1cc(C)c(-c2cccc3c(NC(=O)OC(C)(C)C)c(OC)nn23)c(OC)c1.ClCC1CCCO1>CN(C=O)C.C(C)(=O)OCC>COc1cc(C)c(-c2cccc3c(N(CC4CCCO4)C(=O)OC(C)(C)C)c(OC)nn23)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-32fabf1414554507bbceb57820f051af | COc1cc(C)cc(C)c1-c1cccc2c(NCC3CC3)c(OC)nn12.O=CC1CCOCC1>>COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CCOCC3)CC3CC3)c(OC)nn12 | C(O)([O-])=O.[Na+].C1(CC1)CNC=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)OC.O1CCC(CC1)C=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>C1(CC1)CN(CC1CCOCC1)C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]([NH:17][CH2:25][CH:26]3[CH2:27][CH2:28]3)[c:29]([O:30][CH3:31])[n:32][n:33]12.O=[CH:18][CH:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH... | COc1cc(C)cc(C)c1-c1cccc2c(NCC3CC3)c(OC)nn12.O=CC1CCOCC1 | COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CCOCC3)CC3CC3)c(OC)nn12 | null | null | C(C)(=O)OCC.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 6d9c60e7c47e75322fc9565d992b855788f3516a27cb14d7f9ed299e190b30d3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(-c2cccc3c(N(CC4CCOCC4)CC4CC4)cnn23)cc1 | O=[CH;D2;+0:1]-[C:2](-[C:3])-[C:4].[#8:5]-[c:6]1:[#7;a:7]:[#7;a:8](:[c:9]):[c:10](:[c:11]):[c:12]:1-[NH;D2;+0:13]-[C:14]-[C:15]>>[#8:5]-[c:6]1:[#7;a:7]:[#7;a:8](:[c:9]):[c:10](:[c:11]):[c:12]:1-[N;H0;D3;+0:13](-[C:14]-[C:15])-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4] | 70 | [{"value": 70.0, "product": "C1(CC1)CN(CC1CCOCC1)C=1C(=NN2C1C=CC=C2C2=C(C=C(C=C2C)C)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | After dissolving N-cyclopropylmethyl-N-[2-methoxy-7-(2-methoxy-4,6-dimethylphenyl)pyrazolo[1,5-a]pyridin-3-yl]amine (134 mg) in tetrahydrofuran (10 mL), tetrahydro-2H-4-pyrancarbaldehyde (131 mg) and sodium triacetoxyborohydride (243 mg) were added, and the mixture was stirred at room temperature for 1 hour. Saturated ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | null | null | c1ccccc1.C1CCOCC1.C1CC1.c1ccn2nccc2c1 | Other | C(C)(=O)OCC.O1CCCC1 | null | 1 | COc1cc(C)cc(C)c1-c1cccc2c(NCC3CC3)c(OC)nn12.O=CC1CCOCC1>C(C)(=O)OCC.O1CCCC1>COc1cc(C)cc(C)c1-c1cccc2c(N(CC3CCOCC3)CC3CC3)c(OC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-81978d40133b4b0b88cabb590d06abc3 | Brc1ccccn1.COc1cc(C)cc(C)c1-c1cccc2c(N)c(SC)nn12>>COc1cc(C)cc(C)c1-c1cccc2c(Nc3ccccn3)c(SC)nn12 | COC1=C(C(=CC(=C1)C)C)C1=CC=CC=2N1N=C(C2N)SC.CC(C)([O-])C.[Na+].BrC1=NC=CC=C1.O>>COC1=C(C(=CC(=C1)C)C)C1=CC=CC=2N1N=C(C2NC2=NC=CC=C2)SC | Br[c:18]1[cH:19][cH:20][cH:21][cH:22][n:23]1.[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]([NH2:17])[c:24]([S:25][CH3:26])[n:27][n:28]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][c:8]([CH3:9])[c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]([NH:17][c:18... | Brc1ccccn1.COc1cc(C)cc(C)c1-c1cccc2c(N)c(SC)nn12 | COc1cc(C)cc(C)c1-c1cccc2c(Nc3ccccn3)c(SC)nn12 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2cccc3c(Nc4ccccn4)cnn23)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#16:6]-[c:7]1:[#7;a:8]:[#7;a:9](:[c:10]):[c:11](:[c:12]):[c:13]:1-[NH2;D1;+0:14]>>[#16:6]-[c:7]1:[#7;a:8]:[#7;a:9](:[c:10]):[c:11](:[c:12]):[c:13]:1-[NH;D2;+0:14]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | 120 | CELSIUS | 5 | HOUR | After dissolving [7-(2-methoxy-4,6-dimethylphenyl)-2-(methylsulfanyl)pyrazolo[1,5-a]pyridin-3-yl]amine (40 mg) in toluene (1 mL), 2-bromopyridine (0.013 mL), sodium t-butoxide (25 mg) and dichlorobis(tri-o-tolylphosphine)palladium complex (3 mg) were added and the mixture was heated and stirred at 120° C. for 5 hours. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccn2nccc2c1 | HBr | C1(=CC=CC=C1)C | 120 | 5 | Brc1ccccn1.COc1cc(C)cc(C)c1-c1cccc2c(N)c(SC)nn12>C1(=CC=CC=C1)C>COc1cc(C)cc(C)c1-c1cccc2c(Nc3ccccn3)c(SC)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a6c0895ec1c047d8b96e9207f20ccfd8 | CCc1nn2c(-c3c(OC)cc(C)cc3OC)cccc2c1[N+](=O)[O-]>>CCc1nn2c(-c3c(OC)cc(C)cc3OC)cccc2c1N | COC1=C(C(=CC(=C1)C)OC)C1=CC=CC=2N1N=C(C2[N+](=O)[O-])CC.C(C)(=O)O>>COC1=C(C(=CC(=C1)C)OC)C1=CC=CC=2N1N=C(C2N)CC | O=[N+:23]([O-])[c:22]1[c:3]([CH2:2][CH3:1])[n:4][n:5]2[c:6](-[c:7]3[c:8]([O:9][CH3:10])[cH:11][c:12]([CH3:13])[cH:14][c:15]3[O:16][CH3:17])[cH:18][cH:19][cH:20][c:21]21>>[CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6](-[c:7]3[c:8]([O:9][CH3:10])[cH:11][c:12]([CH3:13])[cH:14][c:15]3[O:16][CH3:17])[cH:18][cH:19][cH:20][c:21]2[c:22]... | CCc1nn2c(-c3c(OC)cc(C)cc3OC)cccc2c1[N+](=O)[O-] | CCc1nn2c(-c3c(OC)cc(C)cc3OC)cccc2c1N | null | [Zn] | O.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2cccc3ccnn23)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3](:[c:4]):[#7;a:5](:[c:6]):[#7;a:7]:[c:8]:1-[C:9]>>[C:9]-[c:8]1:[#7;a:7]:[#7;a:5](:[c:6]):[c:3](:[c:4]):[c:2]:1-[NH2;D1;+0:1] | 91.4 | [{"value": 91.4, "product": "COC1=C(C(=CC(=C1)C)OC)C1=CC=CC=2N1N=C(C2N)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | HOUR | After dissolving 7-(2,6-dimethoxy-4-methylphenyl)-2-ethyl-3-nitropyrazolo[1,5-a]pyridine (600 mg) in a mixture of ethanol (30 mL) and water (30 mL), acetic acid (3 mL) and zinc powder (600 mg) were added and the mixture was stirred at 60° C. for 2 hours. The ethanol of the obtained reaction mixture was distilled off un... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccn2nccc2c1 | Other | [Zn].O.C(C)O | 60 | 2 | CCc1nn2c(-c3c(OC)cc(C)cc3OC)cccc2c1[N+](=O)[O-]>[Zn].O.C(C)O>CCc1nn2c(-c3c(OC)cc(C)cc3OC)cccc2c1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-081cc9df8950478ca48b57a906302cc0 | CCCC1(C(=O)OC)CCC1>>CCCC1(CO)CCC1 | [OH-].[Na+].[Li+].[BH4-].CO.COC(=O)C1(CCC1)CCC>>C(CC)C1(CCC1)CO | CO[C:5]([C:4]1([CH2:3][CH2:2][CH3:1])[CH2:7][CH2:8][CH2:9]1)=[O:6]>>[CH3:1][CH2:2][CH2:3][C:4]1([CH2:5][OH:6])[CH2:7][CH2:8][CH2:9]1 | CCCC1(C(=O)OC)CCC1 | CCCC1(CO)CCC1 | null | null | CCOCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1CCC1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])(-[C:5])-[C:6]>>[C:4]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])(-[C:5])-[C:6] | 87 | [{"value": 87.0, "product": "C(CC)C1(CCC1)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.1, "product": "C(CC)C1(CCC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | LiBH4 (524 mg, 24 mmol) and methanol (1 mL) were added to a 0° C. solution of 1-2 (1.935 g, 11.4 mmol) in ether (22 mL). After 1 h at 0° C. and 1.5 h at room temperature, 41 mL 2 M NaOH was slowly added and the resulting mixture was stirred for 1 h. The mixture was then extracted with dichloromethane (3×40 mL) and the ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1CCC1 | Other | CCOCC | null | 1 | CCCC1(C(=O)OC)CCC1>CCOCC>CCCC1(CO)CCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-421cfd5fe897437b9d9739632c65ce27 | CCCC1(CO)CCC1>>CCCC1(C=O)CCC1 | C[N+]1(CCOCC1)[O-].C(CC)C1(CCC1)CO.C(CC)C1(CCC1)CO>>C(CC)C1(CCC1)C=O | [CH3:1][CH2:2][CH2:3][C:4]1([CH2:5][OH:6])[CH2:7][CH2:8][CH2:9]1>>[CH3:1][CH2:2][CH2:3][C:4]1([CH:5]=[O:6])[CH2:7][CH2:8][CH2:9]1 | CCCC1(CO)CCC1 | CCCC1(C=O)CCC1 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | C1CCC1 | [C:1]-[C:2](-[CH2;D2;+0:3]-[OH;D1;+0:4])(-[C:5])-[C:6]>>[C:1]-[C:2](-[CH;D2;+0:3]=[O;H0;D1;+0:4])(-[C:5])-[C:6] | 218.9 | [{"value": 43.0, "product": "C(CC)C1(CCC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 218.9, "product": "C(CC)C1(CCC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | MINUTE | An ice-cold mixture of 4-methylmorpholine N-oxide (NMO) (1.683 g, 14.4 mmol), 1-3 (1.229 g, 9.59 mmol) and 4 Å molecular sieves (5.5 g) in dichloromethane (20 mL) was treated with tetrapropylammonium perruthenate (TPAP) (179 mg, 0.51 mmol). The mixture was stirred at 0° C. for 5 min. and then was allowed to warm to roo... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1CCC1 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.ClCCl | 0 | 0.083333 | CCCC1(CO)CCC1>[Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.ClCCl>CCCC1(C=O)CCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a1ca73b0fd194eeaa31cf248b261c57b | Brc1ccc(Br)cc1.O=C1CCC1>>OC1(c2ccc(Br)cc2)CCC1 | C1(CCC1)=O.C(CCC)[Li].BrC1=CC=C(C=C1)Br>>BrC1=CC=C(C=C1)C1(CCC1)O | Br[c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1.[O:1]=[C:2]1[CH2:10][CH2:11][CH2:12]1>>[OH:1][C:2]1([c:3]2[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]2)[CH2:10][CH2:11][CH2:12]1 | Brc1ccc(Br)cc1.O=C1CCC1 | OC1(c2ccc(Br)cc2)CCC1 | null | null | C1CCOC1 | C-C Coupling | Grignard_alcohol | 3a5d9845c3d2f80be158f958d196e542d3c9cb0b19bc769081c13a007c24e4af | b8801be51258f6ee39fb6aad45dd9677b1b9eed3d6e0018ffb065bca8e787abf | c1ccc(C2CCC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;H0;D1;+0:6]=[C;H0;D3;+0:7]1-[C:8]-[C:9]-[C:10]-1>>[OH;D1;+0:6]-[C;H0;D4;+0:7]1(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:8]-[C:9]-[C:10]-1 | 54 | [{"value": 54.0, "product": "BrC1=CC=C(C=C1)C1(CCC1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.5, "product": "BrC1=CC=C(C=C1)C1(CCC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | n-Butyllithium (1.2 mL 1.92 mmol, 1.6 M/hexanes) was added to a −78° C. solution of 1,4-dibromobenzene (489 mg, 2.07 mmol) in THF (4.2 mL). After 30 min., a solution of cyclobutanone (141 mg, 2.01 mmol) in 1 mL THF was added by cannula, rinsing with 0.5 mL THF. The reaction was allowed to warm to room temperature and a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone | Tertiary alcohol | c1ccccc1.C1CCC1 | c1ccccc1.C1CCC1 | c1ccccc1.C1CCC1 | Br- | C1CCOC1 | null | 0.5 | Brc1ccc(Br)cc1.O=C1CCC1>C1CCOC1>OC1(c2ccc(Br)cc2)CCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3369d74bfe9e4f18bb09dcce8d3f401e | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F.OC1(c2ccc(Br)cc2)CCC1>>CC(C)(C)[Si](C)(C)OC1(c2ccc(Br)cc2)CCC1 | C(=O)(O)[O-].[Na+].[Si](C)(C)(C(C)(C)C)OS(=O)(=O)C(F)(F)F.BrC1=CC=C(C=C1)C1(CCC1)O.C(C)N(CC)CC>>BrC1=CC=C(C=C1)C1(CCC1)O[Si](C)(C)C(C)(C)C | O=S(=O)(O[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])C(F)(F)F.[OH:8][C:9]1([c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[CH2:17][CH2:18][CH2:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][C:9]1([c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[CH2:17][CH2:18][CH2:19]1 | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F.OC1(c2ccc(Br)cc2)CCC1 | CC(C)(C)[Si](C)(C)OC1(c2ccc(Br)cc2)CCC1 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | 152128cfedc3a22a84819f5fcf8bc01877755d840307ac1d2f4a04a418ed7e06 | 3114efbb5e0c785f11675ccbdf25750cb947c476f01d430ea70f7cc96bcadffe | c1ccc(C2CCC2)cc1 | F-C(-F)(-F)-S(=O)(=O)-O-[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:12]>>[C:8]-[C:9](-[c:11])(-[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:12] | 93 | [{"value": 93.0, "product": "BrC1=CC=C(C=C1)C1(CCC1)O[Si](C)(C)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.7, "product": "BrC1=CC=C(C=C1)C1(CCC1)O[Si](C)(C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | TBSOTf (360 μL, 1.57 mmol) was added to a 0° C. solution of 3-1 (235 mg, 1.04 mmol) and triethylamine (450 μL, 3.23 mmol) in dichloromethane (3 mL). The reaction was allowed to warm to room temperature and after 1 h, saturated NaHCO3 solution was added. The resulting mixture was extracted with ethyl acetate (3×30 mL) a... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Tertiary alcohol.TMS ether protective group | TMS ether protective group | null | null | c1ccccc1.C1CCC1 | TfOH.HO- | ClCCl | null | null | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F.OC1(c2ccc(Br)cc2)CCC1>ClCCl>CC(C)(C)[Si](C)(C)OC1(c2ccc(Br)cc2)CCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-56cee961749d4215a576198071e7b15b | COC(=O)CCC/C=C\C[C@@H]1[C@@H](c2ccc(C(O[Si](C)(C)C(C)(C)C)C3CCCCC3)cc2)[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O.COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1c1ccc(C(O[Si](C)(C)C(C)(C)C)C2CCCCC2)cc1.[NH4+]>>CCCC1(C(O)c2cccc([C@H]3[C@H](O)CC(=O)[C@@H]3C/C=C\CCCC(=O)NCC)c2)CCC1 | OO.CCC([BH-](C(CC)C)C(CC)C)C.[Li+].COC(CCC\C=C/C[C@@H]1[C@H]([C@@H](CC1=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C=C1)C(C1CCCCC1)O[Si](C)(C)C(C)(C)C)=O.C1CCOC1.[NH4+].[Cl-].COC(CCC\C=C/C[C@@H]1[C@H]([C@@H](C[C@@H]1O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C=C1)C(C1CCCCC1)O[Si](C)(C)C(C)(C)C)=O>>C(C)NC(CCC\C=C/C[C@@H]1[C@H]([C@@H](CC1=O)O)C1=... | CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H](O)[C@H](C/C=C\CCCC(=O)O[CH3:28])[C@H]1[c:10]1[cH:9][cH:8][c:7]([CH:5]([CH:4]2[CH2:3][CH2:2][CH2:31][CH2:32][CH2:33]2)[O:6][Si](C)(C)C(C)(C)C)[cH:30][cH:11]1.CC(C)(C)[Si](C)(C)OC(c1ccc([C@H:12]2[C@H:13]([O:14][Si](C)(C)C(C)(C)C)[CH2:15][C:16](=[O:17])[C@@H:18]2[CH2:19]/[CH:20]=[CH:21]\[C... | COC(=O)CCC/C=C\C[C@@H]1[C@@H](c2ccc(C(O[Si](C)(C)C(C)(C)C)C3CCCCC3)cc2)[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O.COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1c1ccc(C(O[Si](C)(C)C(C)(C)C)C2CCCCC2)cc1.[NH4+] | CCCC1(C(O)c2cccc([C@H]3[C@H](O)CC(=O)[C@@H]3C/C=C\CCCC(=O)NCC)c2)CCC1 | null | null | null | Acylation | OtherReaction | 7aa04f3217d6ad7a241d201d3d07feb1c845f7bc217e01dcaf4ccb7a495fc249 | a17dcffa4b04b16f4a5640b70f8e15dde1c81ea8a0a6f337f33f222fc7b4d648 | O=C1CC[C@H](c2cccc(CC3CCC3)c2)C1 | C-C(-C)(-C)-[Si](-C)(-C)-O-C(-C1-C-C-[CH2;D2;+0:1]-C-C-1)-c1:c:c:c(-[C@H;D3;+0:2]2-[C:3](-[O;H0;D2;+0:4]-[Si](-C)(-C)-C(-C)(-C)-C)-[C:5]-[C:6](=[O;D1;H0:7])-[C:8]-2-[C:9]/[C:10]=[C:11]):c:c:1.[C:12]-[C:13]-[C;H0;D3;+0:14](=[O;D1;H0:15])-O-[CH3;D1;+0:16].C-C(-C)(-C)-[Si](-C)(-C)-O-[C@H]1-C-[C@H](-O)-[C@H](-C/C=C\C-C-C-C... | 93 | [{"value": 93.0, "product": "C(C)NC(CCC\\C=C/C[C@@H]1[C@H]([C@@H](CC1=O)O)C1=CC(=CC=C1)C(C1(CCC1)CCC)O)=O", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | Representative procedure for reduction of the C9 ketone: (Z)-7-((1R,2S,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{4-[(tert-butyl-dimethyl-silanyloxy)-cyclohexyl-methyl]-phenyl}-5-hydroxy-cyclopentyl)-hept-5-enoic acid methyl ester (6-1). L-selectride (300 μL, 0.3 mmol, 1 M/THF) was added to a −78° C. solution of keto... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Secondary alcohol.TMS ether protective group.TMS ether protective group.TMS ether protective group.TMS ether protective group | Secondary amide.Secondary alcohol.Secondary alcohol | C1CCCC1.c1ccccc1.C1CCCCC1.c1ccccc1.C1CCCC1.C1CCCCC1 | c1ccccc1.C1CCCC1.C1CCC1 | c1ccccc1.C1CCCC1.C1CCC1 | HO- | null | -78 | 0.5 | COC(=O)CCC/C=C\C[C@@H]1[C@@H](c2ccc(C(O[Si](C)(C)C(C)(C)C)C3CCCCC3)cc2)[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O.COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1c1ccc(C(O[Si](C)(C)C(C)(C)C)C2CCCCC2)cc1.[NH4+]>>CCCC1(C(O)c2cccc([C@H]3[C@H](O)CC(=O)[C@@H]3C/C=C\CCCC(=O)NCC)c2)CCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9f9946512fca429383854066dd37fe03 | COC(=O)CCC/C=C\C[C@@H]1[C@@H](c2ccc(C(O[Si](C)(C)C(C)(C)C)C3CCCCC3)cc2)[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1Cl>>COC(=O)CCC/C=C\C[C@@H]1[C@@H](c2ccc(C(O)C3CCCCC3)cc2)[C@H](O)C[C@H]1Cl | C1=CC=NC=C1.F.COC(CCC\C=C/C[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O[Si](C)(C)C(C)(C)C)C1=CC=C(C=C1)C(C1CCCCC1)O[Si](C)(C)C(C)(C)C)=O>>COC(CCC\C=C/C[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O)C1=CC=C(C=C1)C(O)C1CCCCC1)=O | CC(C)(C)[Si](C)(C)[O:18][CH:17]([c:16]1[cH:15][cH:14][c:13]([C@@H:12]2[C@@H:11]([CH2:10]/[CH:9]=[CH:8]\[CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[C@H:30]([Cl:31])[CH2:29][C@H:27]2[O:28][Si](C)(C)C(C)(C)C)[cH:26][cH:25]1)[CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:... | COC(=O)CCC/C=C\C[C@@H]1[C@@H](c2ccc(C(O[Si](C)(C)C(C)(C)C)C3CCCCC3)cc2)[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1Cl | COC(=O)CCC/C=C\C[C@@H]1[C@@H](c2ccc(C(O)C3CCCCC3)cc2)[C@H](O)C[C@H]1Cl | null | null | CC#N | Deprotection | OtherReaction | 3c4d3a3b788b4022df80488c890c930a0eff3addc93b825229adfe1b23285620 | c96f1dab6a2ddd7b236398a198654bbc85e92a2fc2f6e88d092d4f9a3211cc52 | c1cc(C2CCCC2)ccc1CC1CCCCC1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4].C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:5]-[C:6](-[C:7])-[c:8]>>[C:3]-[C:2](-[OH;D1;+0:1])-[C:4].[C:7]-[C:6](-[OH;D1;+0:5])-[c:8] | 232.6 | [{"value": 93.0, "product": "COC(CCC\\C=C/C[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O)C1=CC=C(C=C1)C(O)C1CCCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 232.6, "product": "COC(CCC\\C=C/C[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O)C1=CC=C(C=C1)C(O)C1CCCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | HF-pyridine (0.60 mL) was added to a 0° C. CH3CN solution of chloride 6-2 (24 mg, 20%) and the mono TBS derivative (36 mg, 36%). The reaction was stirred for 1 h, and then was quenched by addition of saturated NaHCO3 solution. The mixture was extracted with dichloromethane (3×30 mL) and the combined dichloromethane sol... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group.TMS ether protective group | Secondary alcohol.Secondary alcohol | null | null | C1CCCC1.c1ccccc1.C1CCCCC1 | Other | CC#N | null | 1 | COC(=O)CCC/C=C\C[C@@H]1[C@@H](c2ccc(C(O[Si](C)(C)C(C)(C)C)C3CCCCC3)cc2)[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1Cl>CC#N>COC(=O)CCC/C=C\C[C@@H]1[C@@H](c2ccc(C(O)C3CCCCC3)cc2)[C@H](O)C[C@H]1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-505d8cde1f644863b63884fad5906a16 | COc1ccc(CCl)cc1.OCc1ccc(Br)cc1>>COc1ccc(COCc2ccc(Br)cc2)cc1 | [NH4+].[Cl-].BrC1=CC=C(CO)C=C1.[H-].[Na+].COC1=CC=C(CCl)C=C1>>COC1=CC=C(COCC2=CC=C(C=C2)Br)C=C1 | Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18][cH:17]1.[OH:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]2)[cH:17][cH:18]1 | COc1ccc(CCl)cc1.OCc1ccc(Br)cc1 | COc1ccc(COCc2ccc(Br)cc2)cc1 | null | null | C1CCOC1.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccc(COCc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[C:6]-[c:7]>>[c:7]-[C:6]-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 98 | [{"value": 98.0, "product": "COC1=CC=C(COCC2=CC=C(C=C2)Br)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.9, "product": "COC1=CC=C(COCC2=CC=C(C=C2)Br)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A solution of 4-bromobenzyl alcohol (2.011 g, 10.7 mmol) in THF (42 mL) was added to a mixture of NaH (663 mg, 16.6 mmol, 60% in oil) in DMF (13 mL). The mixture was stirred for 1.5 h and 4-methoxybenzyl chloride (MPMCl, 2 mL, 14.8 mmol) was added. After 24 h, 100 mL saturated NH4Cl solution was added. The resulting mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HCl | C1CCOC1.CN(C)C=O | null | 1.5 | COc1ccc(CCl)cc1.OCc1ccc(Br)cc1>C1CCOC1.CN(C)C=O>COc1ccc(COCc2ccc(Br)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bb3f18366ce74ecf87b393633f01ba46 | COC(=O)CCC/C=C\C[C@@H]1[C@@H](c2ccc(CO)cc2)[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1Cl>>COC(=O)CCC/C=C\C[C@@H]1[C@@H](c2ccc(C=O)cc2)[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1Cl | COC(CCC\C=C/C[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O[Si](C)(C)C(C)(C)C)C1=CC=C(C=C1)CO)=O.C[N+]1(CCOCC1)[O-]>>COC(CCC\C=C/C[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O[Si](C)(C)C(C)(C)C)C1=CC=C(C=C1)C=O)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10][C@@H:11]1[C@@H:12]([c:13]2[cH:14][cH:15][c:16]([CH2:17][OH:18])[cH:19][cH:20]2)[C@H:21]([O:22][Si:23]([CH3:24])([CH3:25])[C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][C@H:31]1[Cl:32]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH2:10... | COC(=O)CCC/C=C\C[C@@H]1[C@@H](c2ccc(CO)cc2)[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1Cl | COC(=O)CCC/C=C\C[C@@H]1[C@@H](c2ccc(C=O)cc2)[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1Cl | null | CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(C2CCCC2)cc1 | [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] | 79.7 | [{"value": 79.0, "product": "COC(CCC\\C=C/C[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O[Si](C)(C)C(C)(C)C)C1=CC=C(C=C1)C=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.7, "product": "COC(CCC\\C=C/C[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O[Si](C)(C)C(C)(C)C)C1=CC=C(C=C1)C=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_d... | 0 | CELSIUS | 5 | MINUTE | An ice cold mixture of 9-1 (43 mg, 0.089 mmol), 4 Å molecular sieves (56 mg) and NMO (16 mg, 0.14 mmol) in dichloromethane (0.5 mL) was treated with TPAP (3 mg, 0.009 mmol). The mixture was stirred for 5 min. at 0° C. and then for 1 h at room temperature. The mixture was then filtered through a pad of silica gel, washi... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1CCCC1.c1ccccc1 | null | CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O.ClCCl | 0 | 0.083333 | COC(=O)CCC/C=C\C[C@@H]1[C@@H](c2ccc(CO)cc2)[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1Cl>CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O.ClCCl>COC(=O)CCC/C=C\C[C@@H]1[C@@H](c2ccc(C=O)cc2)[C@H](O[Si](C)(C)C(C)(C)C)C[C@H]1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-41d347d7d83e44799ee2817ae32e4c2a | COC(=O)COCC#CC[C@H]1C(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1c1ccc(C(O[Si](C)(C)C(C)(C)C)C2CCCCC2)cc1>>COC(=O)COCC#CC[C@@H]1[C@@H](c2ccc(C(O[Si](C)(C)C(C)(C)C)C3CCCCC3)cc2)[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O | [NH4+].[Cl-].CCC([BH-](C(CC)C)C(CC)C)C.[Li+].COC(COCC#CC[C@@H]1[C@H]([C@@H](CC1=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C=C1)C(C1CCCCC1)O[Si](C)(C)C(C)(C)C)=O.OO>>COC(COCC#CC[C@@H]1[C@H]([C@@H](C[C@@H]1O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C=C1)C(C1CCCCC1)O[Si](C)(C)C(C)(C)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][CH2:7][C:8]#[C:9][CH2:10][C@@H:11]1[C@@H:12]([c:13]2[cH:14][cH:15][c:16]([CH:17]([O:18][Si:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[CH3:25])[CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]3)[cH:32][cH:33]2)[C@H:34]([O:35][Si:36]([CH3:37])([CH3:38])[C:39]([CH3:40])([CH3:41]... | COC(=O)COCC#CC[C@H]1C(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1c1ccc(C(O[Si](C)(C)C(C)(C)C)C2CCCCC2)cc1 | COC(=O)COCC#CC[C@@H]1[C@@H](c2ccc(C(O[Si](C)(C)C(C)(C)C)C3CCCCC3)cc2)[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O | null | null | C1CCOC1 | Reduction | Reduction of ketone to secondary alcohol | 87d90128b40d1aec3bafae0cf798ca35261f3c820469cb5c329528b3141a9934 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1cc(C2CCCC2)ccc1CC1CCCCC1 | [C:1]#[C:2]-[C:3]-[C:4]1-[C:5]-[C:6]-[C:7]-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]#[C:2]-[C:3]-[C:4]1-[C:5]-[C:6]-[C:7]-[C@@H;D3;+0:8]-1-[OH;D1;+0:9] | 61.9 | [{"value": 61.0, "product": "COC(COCC#CC[C@@H]1[C@H]([C@@H](C[C@@H]1O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C=C1)C(C1CCCCC1)O[Si](C)(C)C(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.9, "product": "COC(COCC#CC[C@@H]1[C@H]([C@@H](C[C@@H]1O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C=C1)C(C1CCCCC1)O[Si](C)(C)C(C)(C)C... | null | null | 1 | HOUR | L-selectride (0.76 mL, 0.76 mmol, 1 M/THF) was added to a −78° C. THF (20 mL) solution of 10-3 (415 mg, 0.63 mmol). The reaction was stirred for 1 h and then 3% H2O2 (14 mL) was added. The resulting mixture was stirred at room temperature for 45 min. and then saturated NH4Cl solution (60 mL) was added. The resulting mi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | C1CCCC1 | C1CCCC1 | C1CCCC1.c1ccccc1.C1CCCCC1 | null | C1CCOC1 | null | 1 | COC(=O)COCC#CC[C@H]1C(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1c1ccc(C(O[Si](C)(C)C(C)(C)C)C2CCCCC2)cc1>C1CCOC1>COC(=O)COCC#CC[C@@H]1[C@@H](c2ccc(C(O[Si](C)(C)C(C)(C)C)C3CCCCC3)cc2)[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c426a0ed2b1a44ed82fd530164038e55 | COC(=O)COCC#CC[C@@H]1[C@@H](c2ccc(C(O)C3CCCCC3)cc2)[C@H](O)C[C@H]1Cl>>COC(=O)COCCCC[C@@H]1[C@@H](c2ccc(C(O)C3CCCCC3)cc2)[C@H](O)C[C@H]1Cl | COC(COCC#CC[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O)C1=CC=C(C=C1)C(O)C1CCCCC1)=O>>COC(COCCCC[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O)C1=CC=C(C=C1)C(O)C1CCCCC1)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][CH2:7][C:8]#[C:9][CH2:10][C@@H:11]1[C@@H:12]([c:13]2[cH:14][cH:15][c:16]([CH:17]([OH:18])[CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)[cH:25][cH:26]2)[C@H:27]([OH:28])[CH2:29][C@H:30]1[Cl:31]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]1[C@@H:12... | COC(=O)COCC#CC[C@@H]1[C@@H](c2ccc(C(O)C3CCCCC3)cc2)[C@H](O)C[C@H]1Cl | COC(=O)COCCCC[C@@H]1[C@@H](c2ccc(C(O)C3CCCCC3)cc2)[C@H](O)C[C@H]1Cl | null | [Pd] | C(C)(=O)OCC | Reduction | OtherReaction | 2bb8d5b532a2781e0a7c069a5cd3e8a7e8d44660c0ec1d9e17c04d8ba2cb383b | 1990560e9c55934bde8ca0feaed9c61d80f37f94f0cf240a9929dc374d0a33aa | c1cc(C2CCCC2)ccc1CC1CCCCC1 | [#8:1]-[C:2]-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[C:5]-[C:6]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C:5]-[C:6] | 75 | [{"value": 75.0, "product": "COC(COCCCC[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O)C1=CC=C(C=C1)C(O)C1CCCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.0, "product": "COC(COCCCC[C@@H]1[C@H]([C@@H](C[C@H]1Cl)O)C1=CC=C(C=C1)C(O)C1CCCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of 10-6 (11 mg, 0.024 mmol) and 5% Pd/C (6 mg, 0.003 mmol) in ethyl acetate (1 mL) was stirred under 1 atm H2 (balloon) for 18 h. The mixture was filtered and evaporated. The residue was purified by preparative TLC on silica gel (45% ethyl acetate/hexanes) to give 11-3 (8 mg, 0.018 mmol, 75%).
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne | null | null | null | C1CCCC1.c1ccccc1.C1CCCCC1 | null | [Pd].C(C)(=O)OCC | null | 18 | COC(=O)COCC#CC[C@@H]1[C@@H](c2ccc(C(O)C3CCCCC3)cc2)[C@H](O)C[C@H]1Cl>[Pd].C(C)(=O)OCC>COC(=O)COCCCC[C@@H]1[C@@H](c2ccc(C(O)C3CCCCC3)cc2)[C@H](O)C[C@H]1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-426359c53dc648d09a60e6e056d141f4 | COC(=O)COc1cccc(CO)c1.II>>COC(=O)COc1cccc(CI)c1 | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.N1C=NC=C1.II.COC(COC1=CC(=CC=C1)CO)=O>>COC(COC1=CC(=CC=C1)CI)=O | O[CH2:12][c:11]1[cH:10][cH:9][cH:8][c:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[cH:14]1.I[I:13]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]([CH2:12][I:13])[cH:14]1 | COC(=O)COc1cccc(CO)c1.II | COC(=O)COc1cccc(CI)c1 | null | null | ClCCl | Functional Group Interconversion | OtherReaction | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccccc1 | I-[I;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[I;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 93 | [{"value": 93.0, "product": "COC(COC1=CC(=CC=C1)CI)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.7, "product": "COC(COC1=CC(=CC=C1)CI)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | Dichloromethane (85 mL) was added to Ph3P (4.942 g, 18.8 mmol), imidazole (1.311 g, 19.3 mmol) and I2 (4.735 g, 18.7 mmol). The mixture was stirred for 5 min. and then a solution of 12-2 (2.937 g, 15.0 mmol) in 15 mL dichloromethane was added by cannula. The reaction was stirred for 3 h, silica gel was added and the mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccccc1 | HI | ClCCl | null | 0.083333 | COC(=O)COc1cccc(CO)c1.II>ClCCl>COC(=O)COc1cccc(CI)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-37fac7bdf06c46dc8609a5f9d997917f | COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1c1ccc2c(c1)CCC2OCc1ccc(OC)cc1>>COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc2c(c1)CCC2OCc1ccc(OC)cc1 | C(=O)(O)[O-].[Na+].COC(CCC\C=C/C[C@@H]1[C@H]([C@@H](CC1=O)O[Si](C)(C)C(C)(C)C)C=1C=C2CCC(C2=CC1)OCC1=CC=C(C=C1)OC)=O.O.C1CCOC1>>COC(CCC\C=C/C[C@@H]1[C@H]([C@@H](CC1=O)O)C=1C=C2CCC(C2=CC1)OCC1=CC=C(C=C1)OC)=O | CC(C)(C)[Si](C)(C)[O:16][C@@H:15]1[CH2:14][C:12](=[O:13])[C@H:11]([CH2:10]/[CH:9]=[CH:8]\[CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[C@H:17]1[c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23]1)[CH2:24][CH2:25][CH:26]2[O:27][CH2:28][c:29]1[cH:30][cH:31][c:32]([O:33][CH3:34])[cH:35][cH:36]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][... | COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1c1ccc2c(c1)CCC2OCc1ccc(OC)cc1 | COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc2c(c1)CCC2OCc1ccc(OC)cc1 | null | null | C(C)(=O)O | Deprotection | Alcohol deprotection from silyl ethers | 050b4fb4e1e9936189860d27dded10ae70a294a642c52f800eb9d5aaef7955cc | 88623e19d23cdfe8e1a4c167fd6cfc51d774a1c784b87a7bb2df8153ee93e67a | O=C1CC[C@H](c2ccc3c(c2)CCC3OCc2ccccc2)C1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]-[C:5]=[O;D1;H0:6]>>[C:3]-[C:2](-[OH;D1;+0:1])-[C:4]-[C:5]=[O;D1;H0:6] | 69.8 | [{"value": 67.0, "product": "COC(CCC\\C=C/C[C@@H]1[C@H]([C@@H](CC1=O)O)C=1C=C2CCC(C2=CC1)OCC1=CC=C(C=C1)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.8, "product": "COC(CCC\\C=C/C[C@@H]1[C@H]([C@@H](CC1=O)O)C=1C=C2CCC(C2=CC1)OCC1=CC=C(C=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired... | null | null | 2 | DAY | A mixture of 15-4 (20 mg, 0.032 mmol) in acetic acid (0.3 mL)/water (0.1 mL)/THF (0.1 mL) was stirred at room temperature. After two days, saturated NaHCO3 solution was added and the resulting mixture was extracted with dichloromethane (3×20 mL). The combined dichloromethane solution was dried (Na2SO4), filtered and ev... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Secondary alcohol | null | null | C1CCCC1.c1ccc2c(c1)CCC2.c1ccccc1 | Other | C(C)(=O)O | null | 48 | COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1c1ccc2c(c1)CCC2OCc1ccc(OC)cc1>C(C)(=O)O>COC(=O)CCC/C=C\C[C@H]1C(=O)C[C@@H](O)[C@@H]1c1ccc2c(c1)CCC2OCc1ccc(OC)cc1 |
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