dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9e8897bc47224a0dafb7c308228916f4 | CCOC1=CCc2cccc(N=C=S)c2C1.[N-]=[N+]=NCC(=O)c1ccc(C(F)(F)F)cc1>>CCOC1=CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 | C(C)OC=1CC2=C(C=CC=C2CC1)N=C=S.N(=[N+]=[N-])CC(=O)C1=CC=C(C=C1)C(F)(F)F.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F | S=[C:13]=[N:12][c:11]1[cH:10][cH:9][cH:8][c:7]2[c:28]1[CH2:29][C:4]([O:3][CH2:2][CH3:1])=[CH:5][CH2:6]2.[N-]=[N+]=[N:14][CH2:15][C:16]([c:17]1[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]1)=[O:27]>>[CH3:1][CH2:2][O:3][C:4]1=[CH:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH:12][c:13]3[n:14][cH:15][c:16... | CCOC1=CCc2cccc(N=C=S)c2C1.[N-]=[N+]=NCC(=O)c1ccc(C(F)(F)F)cc1 | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | 308925f177354ae8700ee398a7647aaf489213eaacf0ba5850c303e603a910c8 | fff1fecf10f43f7b7b2f4a1a42805992525d7d039d15ced016ce6eb268a00bed | C1=CCc2c(cccc2Nc2ncc(-c3ccccc3)o2)C1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[N-]=[N+]=[N;H0;D2;+0:6]-[CH2;D2;+0:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:4]:[c:3](-[NH;D2;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[o;H0;D2;+0:9]:1)... | 22 | [{"value": 22.0, "product": "C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.8, "product": "C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the product of Example 1F (398 mg, 1.72 mmol), the product of Example 1G (473 mg, 2.07 mmol), and triphenyl phosphine (542 mg, 2.07 mmol) in dioxane (9 mL) was heated at 85° C. for 30 min. The solution was cooled to room temperature and evaporated in vacuo. The residue was chromatographed on silica gel, e... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Azide.Isothiocyanate | Secondary amine | null | c1cocn1 | C1=CCc2ccccc2C1.c1cocn1.c1ccccc1 | Other | O1CCOCC1 | null | null | CCOC1=CCc2cccc(N=C=S)c2C1.[N-]=[N+]=NCC(=O)c1ccc(C(F)(F)F)cc1>O1CCOCC1>CCOC1=CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7680cbe7cf2148f68c697c57fd8860cb | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1>>O=C1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 | C(=O)(O)[O-].[Na+].C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F.Cl>>FC(C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O)(F)F | CC[O:1][C:2]1=[CH:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]4)[o:25]3)[c:26]2[CH2:27]1>>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][c:18]([C:19]([F:... | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 | O=C1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 1a0269b029346ab05f1156601c24ee6b4906fe94a4a1e987a93732dd898a7bc6 | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | O=C1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[c:5]:[c:6]-[C:7]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:7]-[c:6]:[c:5]-[C:4]-[CH2;D2;+0:3]-1 | null | [] | 40 | CELSIUS | null | null | A solution of the product of Example 1H (150 mg, 0.375 mmol) in tetrahydrofuran (2.3 mL) was treated with 2N HCl (0.76 mL, 1.52 mmol), and the mixture was heated at 40° C. for 1 hour. After cooling to room temperature, the solution was brought to pH 8 with saturated NaHCO3 solution, and extracted with ethyl acetate. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1=CCc2ccccc2C1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1cocn1.c1ccccc1 | Other | O1CCCC1 | 40 | null | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1>O1CCCC1>O=C1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-804d787557284dee93f51a05aac0e144 | O=C1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1>>OC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 | O.FC(C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O)(F)F.[BH4-].[Na+]>>FC(C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)O)(F)F | [O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]4)[o:25]3)[c:26]2[CH2:27]1>>[OH:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][c:18]([C:19]([F:... | O=C1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 | OC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 | null | null | C(C)O | Reduction | Reduction of ketone to secondary alcohol | 3712a1f2cb52729543ec421b1a5b2fd3f779bad4223604244414834ade516040 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[c:6]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[c:6] | 56.4 | [{"value": 56.0, "product": "FC(C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)O)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.4, "product": "FC(C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | The product of Example 1I (60 mg, 0.161 mmol) in ethanol (6 mL) was treated at 0° C. with NaBH4 (7 mg, 0.184 mmol). The reaction was stirred at 0° C. for 1 hour and was then poured into H2O and extracted with ethyl acetate. The extracts were dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1cocn1.c1ccccc1 | null | C(C)O | 0 | 1 | O=C1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1>C(C)O>OC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c1809d109aec4eaeb4e7f2be076868e2 | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(C(C)(C)C)cc4)o3)c2C1>>CC(C)(C)c1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1 | C(C)(C)(C)C1=CC=C(C=C1)C1=CN=C(O1)NC1=CC=CC=2CC=C(CC12)OCC.C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F>>C(C)(C)(C)C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O | CC[O:22][C:21]1=[CH:23][CH2:24][c:18]2[cH:17][cH:16][cH:15][c:14]([NH:13][c:12]3[n:11][cH:10][c:9](-[c:8]4[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:27][cH:26]4)[o:25]3)[c:19]2[CH2:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][cH:17][c:18]4... | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(C(C)(C)C)cc4)o3)c2C1 | CC(C)(C)c1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1 | null | null | null | Miscellaneous | OtherReaction | 1a0269b029346ab05f1156601c24ee6b4906fe94a4a1e987a93732dd898a7bc6 | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | O=C1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[c:5]:[c:6]-[C:7]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:7]-[c:6]:[c:5]-[C:4]-[CH2;D2;+0:3]-1 | null | [] | null | null | null | null | The title compound was prepared using the procedure of Example 1I, substituting the product of Example 3A for the product of Example 1H.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1=CCc2ccccc2C1 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1cocn1.c1ccc2c(c1)CCCC2 | Other | null | null | null | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(C(C)(C)C)cc4)o3)c2C1>>CC(C)(C)c1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa326e3b66bb4c98a883b2eb808cbfbf | CC(C)(C)c1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1>>CC(C)(C)c1ccc(-c2cnc(Nc3cccc4c3CC(O)CC4)o2)cc1 | C(C)(C)(C)C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O.FC(C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O)(F)F>>C(C)(C)(C)C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)O | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][cH:17][c:18]4[c:19]3[CH2:20][C:21](=[O:22])[CH2:23][CH2:24]4)[o:25]2)[cH:26][cH:27]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][cH:17][c:18]4[... | CC(C)(C)c1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1 | CC(C)(C)c1ccc(-c2cnc(Nc3cccc4c3CC(O)CC4)o2)cc1 | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 3712a1f2cb52729543ec421b1a5b2fd3f779bad4223604244414834ade516040 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[c:6]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound was prepared using the procedure of Example 2, substituting the product of Example 3B for the product of Example 1I. 1H NMR (DMSO-d6) δ 9.07 (s, 1H), 7.58 (d, 1H, J=5.4 Hz), 7.46 (m, 3H), 7.30 (s, 1H), 7.08 (t, 1H, J=7.8 Hz), 6.83 (d, 1H, J=7.1 Hz), 4.80 (d, 1H, J=4.0 Hz), 3.91 (m, 1H), 2.72-2.96 (m,... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1cocn1.c1ccc2c(c1)CCCC2 | null | null | null | null | CC(C)(C)c1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1>>CC(C)(C)c1ccc(-c2cnc(Nc3cccc4c3CC(O)CC4)o2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-82859ca2f93d4f94a8a7922cf8f94173 | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(Cl)cc4)o3)c2C1>>O=C1CCc2cccc(Nc3ncc(-c4ccc(Cl)cc4)o3)c2C1 | ClC1=CC=C(C=C1)C1=CN=C(O1)NC1=CC=CC=2CC=C(CC12)OCC.C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F>>ClC1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O | CC[O:1][C:2]1=[CH:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]4)[o:22]3)[c:23]2[CH2:24]1>>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]4)[o:22]3... | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(Cl)cc4)o3)c2C1 | O=C1CCc2cccc(Nc3ncc(-c4ccc(Cl)cc4)o3)c2C1 | null | null | null | Miscellaneous | OtherReaction | 1a0269b029346ab05f1156601c24ee6b4906fe94a4a1e987a93732dd898a7bc6 | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | O=C1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[c:5]:[c:6]-[C:7]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:7]-[c:6]:[c:5]-[C:4]-[CH2;D2;+0:3]-1 | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 1I, substituting the product of Example 6B for the product of Example 1H.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1=CCc2ccccc2C1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1cocn1.c1ccccc1 | Other | null | null | null | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(Cl)cc4)o3)c2C1>>O=C1CCc2cccc(Nc3ncc(-c4ccc(Cl)cc4)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74e50e6b16b24894bbb79a422cd58a83 | O=C1CCc2cccc(Nc3ncc(-c4ccc(Cl)cc4)o3)c2C1>>OC1CCc2cccc(Nc3ncc(-c4ccc(Cl)cc4)o3)c2C1 | ClC1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O.FC(C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O)(F)F>>ClC1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)O | [O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]4)[o:22]3)[c:23]2[CH2:24]1>>[OH:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]4)[o:22]3... | O=C1CCc2cccc(Nc3ncc(-c4ccc(Cl)cc4)o3)c2C1 | OC1CCc2cccc(Nc3ncc(-c4ccc(Cl)cc4)o3)c2C1 | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 3712a1f2cb52729543ec421b1a5b2fd3f779bad4223604244414834ade516040 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[c:6]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 2, substituting the product of Example 6C for the product of Example 1I. 1H NMR (DMSO-d6) δ 9.16 (s, 1H), 7.43-7.57 (m, 6H), 7.09 (t, 1H, J=7.4 Hz), 6.83 (d, 1H, J=7.0 Hz), 4.80 (d, 1H, J=3.7 Hz), 3.92 (m, 1H), 2.72-2.98 (m, 4H), 1.86 (m, 1H), ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1cocn1.c1ccccc1 | null | null | null | null | O=C1CCc2cccc(Nc3ncc(-c4ccc(Cl)cc4)o3)c2C1>>OC1CCc2cccc(Nc3ncc(-c4ccc(Cl)cc4)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b79294e77d5c4d0e979ae029fe326835 | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1.CCOC1=CCc2cccc(Nc3ncc(-c4ccc(Cl)cc4)o3)c2C1>>O=C1CCc2cccc(Nc3ncc(-c4ccc(N5CCCC5)cc4)o3)c2C1 | ClC1=CC=C(C=C1)C1=CN=C(O1)NC1=CC=CC=2CC=C(CC12)OCC.C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F>>N1(CCCC1)C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O | FC(F)(F)c1ccc(-c2cnc([NH:19]c3cccc4c3CC(O[CH2:20][CH3:21])=CC4)o2)cc1.Cl[c:18]1[cH:17][cH:16][c:15](-[c:14]2[cH:13][n:12][c:11]([NH:10][c:9]3[cH:8][cH:7][cH:6][c:5]4[c:27]3[CH2:28][C:2]([O:1][CH2:23][CH3:22])=[CH:3][CH2:4]4)[o:26]2)[cH:25][cH:24]1>>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[... | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1.CCOC1=CCc2cccc(Nc3ncc(-c4ccc(Cl)cc4)o3)c2C1 | O=C1CCc2cccc(Nc3ncc(-c4ccc(N5CCCC5)cc4)o3)c2C1 | null | null | null | Acylation | OtherReaction | ee6c3a3c4ca9ccdc52a76a8208d2cbb288a6cf74ee0defb0da6208a0b58da0a8 | b71102a2a9381d5ea5cdf4f6200e7d5ba1948fedd5bb89a81ed64c935f28b70d | O=C1CCc2cccc(Nc3ncc(-c4ccc(N5CCCC5)cc4)o3)c2C1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH3;D1;+0:6]-[CH2;D2;+0:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:9]1=[CH;D2;+0:10]-[C:11]-[c:12]:[c:13]-[C:14]-1.F-C(-F)(-F)-c1:c:c:c(-c2:c:n:c(-[NH;D2;+0:15]-c3:c:c:c:c4:c:3-C-C(-O-[CH2;D2;+0:16]-[CH3;D1;+0:17])=C-C-4):o:2):c:c:1>>[O;H0;D1;+0:8]=[C;H0;D3;+0:9]1-[C:14]-[c:13]:[c:12]-[C... | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 1I, substituting the product of Example 7B for the product of Example 1H.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Ether.Ether.Secondary amine | Ketone.Tertiary amine | c1ccccc1.c1cocn1.C1=CCc2ccccc2C1.c1ccccc1.C1=CCc2ccccc2C1 | c1ccc2c(c1)CCCC2.c1ccccc1.C1CC[NH]C1 | c1ccc2c(c1)CCCC2.c1cocn1.c1ccccc1.C1CC[NH]C1 | HF | null | null | null | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1.CCOC1=CCc2cccc(Nc3ncc(-c4ccc(Cl)cc4)o3)c2C1>>O=C1CCc2cccc(Nc3ncc(-c4ccc(N5CCCC5)cc4)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1b3163007d4442298e13965c3baf5a21 | O=C1CCc2cccc(Nc3ncc(-c4ccc(N5CCCC5)cc4)o3)c2C1>>OC1CCc2cccc(Nc3ncc(-c4ccc(N5CCCC5)cc4)o3)c2C1 | N1(CCCC1)C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O.FC(C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O)(F)F>>N1(CCCC1)C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)O | [O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][c:18]([N:19]5[CH2:20][CH2:21][CH2:22][CH2:23]5)[cH:24][cH:25]4)[o:26]3)[c:27]2[CH2:28]1>>[OH:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][c:18... | O=C1CCc2cccc(Nc3ncc(-c4ccc(N5CCCC5)cc4)o3)c2C1 | OC1CCc2cccc(Nc3ncc(-c4ccc(N5CCCC5)cc4)o3)c2C1 | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 3712a1f2cb52729543ec421b1a5b2fd3f779bad4223604244414834ade516040 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1cc2c(c(Nc3ncc(-c4ccc(N5CCCC5)cc4)o3)c1)CCCC2 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[c:6]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 2, substituting the product of Example 7C for the product of Example 1I. 1H NMR (DMSO-d6) δ 8.86 (s, 1H), 7.61 (d, 2H, J=7.2 Hz), 7.37 (d, 1H, J=8.9 Hz), 7.07 (t, 1H, J=7.8 Hz), 7.02 (s, 1H), 6.80 (d, 1H, J=8.2 Hz), 6.57 (d, 2H, J=8.8 Hz), 4.79... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1cocn1.c1ccccc1.C1CC[NH]C1 | null | null | null | null | O=C1CCc2cccc(Nc3ncc(-c4ccc(N5CCCC5)cc4)o3)c2C1>>OC1CCc2cccc(Nc3ncc(-c4ccc(N5CCCC5)cc4)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3efeac350b1f49f39269681ba7eceaf9 | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(Br)cc4)o3)c2C1>>O=C1CCc2cccc(Nc3ncc(-c4ccc(Br)cc4)o3)c2C1 | BrC1=CC=C(C=C1)C1=CN=C(O1)NC1=CC=CC=2CC=C(CC12)OCC.C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F>>BrC1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O | CC[O:1][C:2]1=[CH:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][c:18]([Br:19])[cH:20][cH:21]4)[o:22]3)[c:23]2[CH2:24]1>>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][c:18]([Br:19])[cH:20][cH:21]4)[o:22]3... | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(Br)cc4)o3)c2C1 | O=C1CCc2cccc(Nc3ncc(-c4ccc(Br)cc4)o3)c2C1 | null | null | null | Miscellaneous | OtherReaction | 1a0269b029346ab05f1156601c24ee6b4906fe94a4a1e987a93732dd898a7bc6 | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | O=C1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[c:5]:[c:6]-[C:7]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:7]-[c:6]:[c:5]-[C:4]-[CH2;D2;+0:3]-1 | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 1I, substituting the product of Example 8B for the product of Example 1H.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1=CCc2ccccc2C1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1cocn1.c1ccccc1 | Other | null | null | null | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(Br)cc4)o3)c2C1>>O=C1CCc2cccc(Nc3ncc(-c4ccc(Br)cc4)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e0b39b2ec77b4b99b7fdf647f68a432b | O=C1CCc2cccc(Nc3ncc(-c4ccc(Br)cc4)o3)c2C1>>OC1CCc2cccc(Nc3ncc(-c4ccc(Br)cc4)o3)c2C1 | BrC1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O.FC(C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O)(F)F>>BrC1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)O | [O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][c:18]([Br:19])[cH:20][cH:21]4)[o:22]3)[c:23]2[CH2:24]1>>[OH:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][c:18]([Br:19])[cH:20][cH:21]4)[o:22]3... | O=C1CCc2cccc(Nc3ncc(-c4ccc(Br)cc4)o3)c2C1 | OC1CCc2cccc(Nc3ncc(-c4ccc(Br)cc4)o3)c2C1 | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 3712a1f2cb52729543ec421b1a5b2fd3f779bad4223604244414834ade516040 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[c:6]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 2, substituting the product of Example 8C for the product of Example 1I. 1H NMR (DMSO-d6) 69.17 (s, 1H), 7.43-7.57 (m, 6H), 7.10 (t, 1H, J=7.3 Hz), 6.81 (d, 1H, J=6.8 Hz), 4.80 (d, 1H, J=3.9 Hz), 3.90 (m, 1H), 2.68-2.96 (m, 4H), 1.82 (m, 1H), 1... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1cocn1.c1ccccc1 | null | null | null | null | O=C1CCc2cccc(Nc3ncc(-c4ccc(Br)cc4)o3)c2C1>>OC1CCc2cccc(Nc3ncc(-c4ccc(Br)cc4)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2430a2baa1bb4b2082efd8924dadceda | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(C)cc4)o3)c2C1>>Cc1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1 | C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C.C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F>>CC1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O | CC[O:19][C:18]1=[CH:20][CH2:21][c:15]2[cH:14][cH:13][cH:12][c:11]([NH:10][c:9]3[n:8][cH:7][c:6](-[c:5]4[cH:4][cH:3][c:2]([CH3:1])[cH:24][cH:23]4)[o:22]3)[c:16]2[CH2:17]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[CH2:17][C:18](=[O:19])[CH2:20][CH2:21]4)[o:2... | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(C)cc4)o3)c2C1 | Cc1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1 | null | null | null | Miscellaneous | OtherReaction | 1a0269b029346ab05f1156601c24ee6b4906fe94a4a1e987a93732dd898a7bc6 | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | O=C1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[c:5]:[c:6]-[C:7]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:7]-[c:6]:[c:5]-[C:4]-[CH2;D2;+0:3]-1 | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 1I, substituting the product of Example 9B for the product of Example 1H.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1=CCc2ccccc2C1 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1cocn1.c1ccc2c(c1)CCCC2 | Other | null | null | null | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(C)cc4)o3)c2C1>>Cc1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-df39debac6d94c92831d67bc336bea26 | Cc1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1>>Cc1ccc(-c2cnc(Nc3cccc4c3CC(O)CC4)o2)cc1 | CC1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O.FC(C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O)(F)F>>CC1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)O | [CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[CH2:17][C:18](=[O:19])[CH2:20][CH2:21]4)[o:22]2)[cH:23][cH:24]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[CH2:17][CH:18]([OH:19])[CH2:20][CH2:21]4)[o:2... | Cc1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1 | Cc1ccc(-c2cnc(Nc3cccc4c3CC(O)CC4)o2)cc1 | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 3712a1f2cb52729543ec421b1a5b2fd3f779bad4223604244414834ade516040 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[c:6]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 2, substituting the product of Example 9C for the product of Example 1I. 1H NMR (DMSO-d6) δ 9.05 (s, 1H), 7.58 (m, 1H), 7.44 (m, 2H), 7.29 (s, 1H), 7.19 (m, 2H), 7.06 (t, 1H, J=7.5 Hz), 6.83 (d, 1H, J=7.0 Hz), 4.80 (d, 1H, J=4.0 Hz), 3.92 (m, 1... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1cocn1.c1ccc2c(c1)CCCC2 | null | null | null | null | Cc1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1>>Cc1ccc(-c2cnc(Nc3cccc4c3CC(O)CC4)o2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f19b857cf5cc40d7ac8b80a2e7c73a4f | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(OC)cc4)o3)c2C1>>COc1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1 | C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)OC.C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F>>COC1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O | CC[O:20][C:19]1=[CH:21][CH2:22][c:16]2[cH:15][cH:14][cH:13][c:12]([NH:11][c:10]3[n:9][cH:8][c:7](-[c:6]4[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:25][cH:24]4)[o:23]3)[c:17]2[CH2:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][cH:15][c:16]4[c:17]3[CH2:18][C:19](=[O:20])[CH2:21][C... | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(OC)cc4)o3)c2C1 | COc1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1 | null | null | null | Miscellaneous | OtherReaction | 1a0269b029346ab05f1156601c24ee6b4906fe94a4a1e987a93732dd898a7bc6 | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | O=C1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[c:5]:[c:6]-[C:7]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:7]-[c:6]:[c:5]-[C:4]-[CH2;D2;+0:3]-1 | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 11, substituting the product of Example 10B for the product of Example 1H.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1=CCc2ccccc2C1 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1cocn1.c1ccc2c(c1)CCCC2 | Other | null | null | null | CCOC1=CCc2cccc(Nc3ncc(-c4ccc(OC)cc4)o3)c2C1>>COc1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6d9a2a79dfd9410fab25d3fb90c9140a | COc1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1>>COc1ccc(-c2cnc(Nc3cccc4c3CC(O)CC4)o2)cc1 | COC1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O.FC(C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O)(F)F>>COC1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][cH:15][c:16]4[c:17]3[CH2:18][C:19](=[O:20])[CH2:21][CH2:22]4)[o:23]2)[cH:24][cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][cH:15][c:16]4[c:17]3[CH2:18][CH:19]([OH:20])[CH2:21][C... | COc1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1 | COc1ccc(-c2cnc(Nc3cccc4c3CC(O)CC4)o2)cc1 | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 3712a1f2cb52729543ec421b1a5b2fd3f779bad4223604244414834ade516040 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[c:6]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 2, substituting the product of Example 10C for the product of Example 1I. 1H NMR (DMSO-d6) δ 8.98 (s, 1H), 7.59 (d, 1H, J=7.8 Hz), 7.49 (d, 2H, J=8.8 Hz), 7.20 (s, 1H), 7.08 (t, 1H, J=7.6 Hz), 7.00 (d, 2H, J=8.8 Hz), 6.82 (d, 1H, J=7.4 Hz), 4.7... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1cocn1.c1ccc2c(c1)CCCC2 | null | null | null | null | COc1ccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)cc1>>COc1ccc(-c2cnc(Nc3cccc4c3CC(O)CC4)o2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac52da6b80b741f98f01699c0a3acced | CCOC1=CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1>>O=C1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 | C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=CC=C1.C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F>>C1(=CC=CC=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O | CC[O:1][C:2]1=[CH:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[o:21]3)[c:22]2[CH2:23]1>>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[o:21]3)[c:22]2[CH2:23]... | CCOC1=CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 | O=C1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 | null | null | null | Miscellaneous | OtherReaction | 1a0269b029346ab05f1156601c24ee6b4906fe94a4a1e987a93732dd898a7bc6 | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | O=C1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[c:5]:[c:6]-[C:7]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:7]-[c:6]:[c:5]-[C:4]-[CH2;D2;+0:3]-1 | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 1I, substituting the product of Example 11B for the product of Example 1H.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1=CCc2ccccc2C1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1cocn1.c1ccccc1 | Other | null | null | null | CCOC1=CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1>>O=C1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b104f7949564704b58f3de63e4cd4fe | O=C1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1>>OC1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 | C1(=CC=CC=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O.FC(C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O)(F)F>>C1(=CC=CC=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)O | [O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[o:21]3)[c:22]2[CH2:23]1>>[OH:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[o:21]3)[c:22]2[CH2:23]... | O=C1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 | OC1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 3712a1f2cb52729543ec421b1a5b2fd3f779bad4223604244414834ade516040 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[c:6]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 2, substituting the product of Example 11C for the product of Example 1I. 1H NMR (DMSO-d6) 9.11 (s, 1H), 7.59 (m, 3H), 7.41 (t, 2H, J=7.7 Hz), 7.37 (s, 1H), 7.25 (t, 1H, J=7.5 Hz), 7.09 (t, 1H, J=7.5 Hz), 6.84 (d, 1H, J=7.1 Hz), 4.80 (d, 1H, J=... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1cocn1.c1ccccc1 | null | null | null | null | O=C1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1>>OC1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5950d5627c664a5ea6e6310d5fd5e86f | CCOC1=CCc2cccc(Nc3ncc(C45CC6CC(CC(C6)C4)C5)o3)c2C1>>O=C1CCc2cccc(Nc3ncc(C45CC6CC(CC(C6)C4)C5)o3)c2C1 | C12(CC3CC(CC(C1)C3)C2)C2=CN=C(O2)NC2=CC=CC=3CC=C(CC23)OCC.C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F>>C12(CC3CC(CC(C1)C3)C2)C2=CN=C(O2)NC=2C=CC=C3CCC(CC23)=O | CC[O:1][C:2]1=[CH:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([C:15]45[CH2:16][CH:17]6[CH2:18][CH:19]([CH2:20][CH:21]([CH2:22]6)[CH2:23]4)[CH2:24]5)[o:25]3)[c:26]2[CH2:27]1>>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([C:15]45[CH2:16][CH:17]6[CH... | CCOC1=CCc2cccc(Nc3ncc(C45CC6CC(CC(C6)C4)C5)o3)c2C1 | O=C1CCc2cccc(Nc3ncc(C45CC6CC(CC(C6)C4)C5)o3)c2C1 | null | null | null | Miscellaneous | OtherReaction | 1a0269b029346ab05f1156601c24ee6b4906fe94a4a1e987a93732dd898a7bc6 | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | O=C1CCc2cccc(Nc3ncc(C45CC6CC(CC(C6)C4)C5)o3)c2C1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[c:5]:[c:6]-[C:7]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:7]-[c:6]:[c:5]-[C:4]-[CH2;D2;+0:3]-1 | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 1I, substituting the product of Example 12B for the product of Example 1H.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1=CCc2ccccc2C1 | c1ccc2c(c1)CCCC2 | c1cocn1.c1ccc2c(c1)CCCC2.C1C2CC3CC1CC(C2)C3 | Other | null | null | null | CCOC1=CCc2cccc(Nc3ncc(C45CC6CC(CC(C6)C4)C5)o3)c2C1>>O=C1CCc2cccc(Nc3ncc(C45CC6CC(CC(C6)C4)C5)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4c6a465caecf436582303e48303a9e11 | CCOC1=CCc2cccc(Nc3ncc(C)o3)c2C1>>Cc1cnc(Nc2cccc3c2CC(=O)CC3)o1 | C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C.C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F>>CC1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O | CC[O:15][C:14]1=[CH:16][CH2:17][c:11]2[cH:10][cH:9][cH:8][c:7]([NH:6][c:5]3[n:4][cH:3][c:2]([CH3:1])[o:18]3)[c:12]2[CH2:13]1>>[CH3:1][c:2]1[cH:3][n:4][c:5]([NH:6][c:7]2[cH:8][cH:9][cH:10][c:11]3[c:12]2[CH2:13][C:14](=[O:15])[CH2:16][CH2:17]3)[o:18]1 | CCOC1=CCc2cccc(Nc3ncc(C)o3)c2C1 | Cc1cnc(Nc2cccc3c2CC(=O)CC3)o1 | null | null | null | Miscellaneous | OtherReaction | 1a0269b029346ab05f1156601c24ee6b4906fe94a4a1e987a93732dd898a7bc6 | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | O=C1CCc2cccc(Nc3ncco3)c2C1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[c:5]:[c:6]-[C:7]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:7]-[c:6]:[c:5]-[C:4]-[CH2;D2;+0:3]-1 | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 1I, substituting the product of Example 13B for the product of Example 1H.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1=CCc2ccccc2C1 | c1ccc2c(c1)CCCC2 | c1cocn1.c1ccc2c(c1)CCCC2 | Other | null | null | null | CCOC1=CCc2cccc(Nc3ncc(C)o3)c2C1>>Cc1cnc(Nc2cccc3c2CC(=O)CC3)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c46d095cb52b4ad0a7f9d648e0710420 | CCOC1=CCc2cccc(Nc3ncc(-c4ccccc4C)o3)c2C1>>Cc1ccccc1-c1cnc(Nc2cccc3c2CC(=O)CC3)o1 | C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=C(C=CC=C1)C.C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F>>CC1=C(C=CC=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O | CC[O:21][C:20]1=[CH:22][CH2:23][c:17]2[cH:16][cH:15][cH:14][c:13]([NH:12][c:11]3[n:10][cH:9][c:8](-[c:7]4[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]4)[o:24]3)[c:18]2[CH2:19]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][n:10][c:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][c:17]3[c:18]2[CH2:19][C:20](=[O:21])[CH2:22]... | CCOC1=CCc2cccc(Nc3ncc(-c4ccccc4C)o3)c2C1 | Cc1ccccc1-c1cnc(Nc2cccc3c2CC(=O)CC3)o1 | null | null | null | Miscellaneous | OtherReaction | 1a0269b029346ab05f1156601c24ee6b4906fe94a4a1e987a93732dd898a7bc6 | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | O=C1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[c:5]:[c:6]-[C:7]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:7]-[c:6]:[c:5]-[C:4]-[CH2;D2;+0:3]-1 | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 11, substituting the product of Example 14B for the product of Example 1H.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1=CCc2ccccc2C1 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1cocn1.c1ccc2c(c1)CCCC2 | Other | null | null | null | CCOC1=CCc2cccc(Nc3ncc(-c4ccccc4C)o3)c2C1>>Cc1ccccc1-c1cnc(Nc2cccc3c2CC(=O)CC3)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-68253aafbae44171a40585fd4b90a0f6 | CCOC1=CCc2cccc(Nc3ncc(-c4cccc(C)c4)o3)c2C1>>Cc1cccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)c1 | C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC(=CC=C1)C.C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F>>CC=1C=C(C=CC1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O | CC[O:20][C:19]1=[CH:21][CH2:22][c:16]2[cH:15][cH:14][cH:13][c:12]([NH:11][c:10]3[n:9][cH:8][c:7](-[c:6]4[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:24]4)[o:23]3)[c:17]2[CH2:18]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][cH:15][c:16]4[c:17]3[CH2:18][C:19](=[O:20])[CH2:21][CH2:22... | CCOC1=CCc2cccc(Nc3ncc(-c4cccc(C)c4)o3)c2C1 | Cc1cccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)c1 | null | null | null | Miscellaneous | OtherReaction | 1a0269b029346ab05f1156601c24ee6b4906fe94a4a1e987a93732dd898a7bc6 | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | O=C1CCc2cccc(Nc3ncc(-c4ccccc4)o3)c2C1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[c:5]:[c:6]-[C:7]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:7]-[c:6]:[c:5]-[C:4]-[CH2;D2;+0:3]-1 | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 11, substituting the product of Example 15B for the product of Example 1H.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1=CCc2ccccc2C1 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1cocn1.c1ccc2c(c1)CCCC2 | Other | null | null | null | CCOC1=CCc2cccc(Nc3ncc(-c4cccc(C)c4)o3)c2C1>>Cc1cccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f483c9fe863e4f228bd6307a1ed68794 | Cc1cccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)c1>>Cc1cccc(-c2cnc(Nc3cccc4c3CC(O)CC4)o2)c1 | CC=1C=C(C=CC1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O.FC(C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O)(F)F>>CC=1C=C(C=CC1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][cH:15][c:16]4[c:17]3[CH2:18][C:19](=[O:20])[CH2:21][CH2:22]4)[o:23]2)[cH:24]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][cH:15][c:16]4[c:17]3[CH2:18][CH:19]([OH:20])[CH2:21][CH2:22... | Cc1cccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)c1 | Cc1cccc(-c2cnc(Nc3cccc4c3CC(O)CC4)o2)c1 | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 3712a1f2cb52729543ec421b1a5b2fd3f779bad4223604244414834ade516040 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[c:6]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 2, substituting the product of Example 15C for the product of Example 1I. 1H NMR (DMSO-d6) δ 9.08 (s, 1H), 7.58 (d, 1H, J=7.3 Hz), 7.26-7.39 (m, 4H), 7.04-7.12 (m, 2H), 6.83 (d, 1H, J=7.2 Hz), 4.81 (d, 1H, J=4.1 Hz), 3.93 (m, 1H), 2.73-2.97 (m,... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccccc1.c1cocn1.c1ccc2c(c1)CCCC2 | null | null | null | null | Cc1cccc(-c2cnc(Nc3cccc4c3CC(=O)CC4)o2)c1>>Cc1cccc(-c2cnc(Nc3cccc4c3CC(O)CC4)o2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bf899221f4fe47c0b99b1dc338c08f08 | BrCC1CO1.[Br][Mg][c]1ccccc1>>O=C(CBr)Cc1ccccc1 | O.C1(=CC=CC=C1)[Mg]Br.CC(=O)C.OS(=O)(=O)O.O=[Cr](=O)=O.C(Br)C1CO1>>BrCC(=O)CC1=CC=CC=C1 | [O:1]1[CH:2]([CH2:3][Br:4])[CH2:5]1.[Br][Mg][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[O:1]=[C:2]([CH2:3][Br:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | BrCC1CO1.[Br][Mg][c]1ccccc1 | O=C(CBr)Cc1ccccc1 | null | null | CC(=O)C.CCOCC | Acylation | OtherReaction | b10aa97a76eb9a89cd16304370084ba47308e8607bfd81a097d78135f98df871 | ec0ff780af42fae85b60f090ef0fa45884a198379b921e4e98688b67ac549630 | c1ccccc1 | [Br;D1;H0:1]-[C:2]-[CH;D3;+0:3]1-[CH2;D2;+0:4]-[O;H0;D2;+0:5]-1.[Br]-[Mg]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[Br;D1;H0:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:5])-[CH2;D2;+0:4]-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10] | 75.1 | [{"value": 75.0, "product": "BrCC(=O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.1, "product": "BrCC(=O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a suspension of CuBr (0.143 g, 0.997 mmol) in 25 mL dry ether was slowly added 1M phenylmagnesium bromide (10 mL, 10 mmol). Epibromohydrin (0.87 mL, 10.5 mmol) was then added dropwise. The reaction mixture was allowed to stir at −78° C. to room temperature overnight, poured into H2O and extracted with ether. The ext... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ether | Ketone | C1CO1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr.Mg | CC(=O)C.CCOCC | null | 8 | BrCC1CO1.[Br][Mg][c]1ccccc1>CC(=O)C.CCOCC>O=C(CBr)Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-235038e28aa0409f94bae4047a9eabcc | CCOC1=CCc2cccc(Nc3ncc(Cc4ccccc4)o3)c2C1>>O=C1CCc2cccc(Nc3ncc(Cc4ccccc4)o3)c2C1 | C(C1=CC=CC=C1)C1=CN=C(O1)NC1=CC=CC=2CC=C(CC12)OCC.C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F>>C(C1=CC=CC=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O | CC[O:1][C:2]1=[CH:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([CH2:15][c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21]4)[o:22]3)[c:23]2[CH2:24]1>>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([CH2:15][c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21]4)[o:22]3)[... | CCOC1=CCc2cccc(Nc3ncc(Cc4ccccc4)o3)c2C1 | O=C1CCc2cccc(Nc3ncc(Cc4ccccc4)o3)c2C1 | null | null | null | Miscellaneous | OtherReaction | 1a0269b029346ab05f1156601c24ee6b4906fe94a4a1e987a93732dd898a7bc6 | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | O=C1CCc2cccc(Nc3ncc(Cc4ccccc4)o3)c2C1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[c:5]:[c:6]-[C:7]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:7]-[c:6]:[c:5]-[C:4]-[CH2;D2;+0:3]-1 | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 1I, substituting the product of Example 16C for the product of Example 1H.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1=CCc2ccccc2C1 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1cocn1.c1ccccc1 | Other | null | null | null | CCOC1=CCc2cccc(Nc3ncc(Cc4ccccc4)o3)c2C1>>O=C1CCc2cccc(Nc3ncc(Cc4ccccc4)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-12beb2aa96624c63870a72e0e7136262 | O=C1CCc2cccc(Nc3ncc(Cc4ccccc4)o3)c2C1>>OC1CCc2cccc(Nc3ncc(Cc4ccccc4)o3)c2C1 | C(C1=CC=CC=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O.FC(C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O)(F)F>>C(C1=CC=CC=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)O | [O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([CH2:15][c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21]4)[o:22]3)[c:23]2[CH2:24]1>>[OH:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]([CH2:15][c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21]4)[o:22]3)[... | O=C1CCc2cccc(Nc3ncc(Cc4ccccc4)o3)c2C1 | OC1CCc2cccc(Nc3ncc(Cc4ccccc4)o3)c2C1 | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 3712a1f2cb52729543ec421b1a5b2fd3f779bad4223604244414834ade516040 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(Cc2cnc(Nc3cccc4c3CCCC4)o2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[c:6]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 2, substituting the product of Example 16D for the product of Example 1I. 1H NMR (DMSO-d6) δ 8.72 (s, 1H), 7.56-7.63 (m, 3H), 7.23-7.37 (m, 3H), 7.02 (t, 1H, J=7.5 Hz), 6.77 (d, 1H, J=7.3 Hz), 6.56 (s, 1H), 4.74 (d, 1H, J=3.7 Hz), 3.93 (s, 2H),... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2.c1cocn1.c1ccccc1 | null | null | null | null | O=C1CCc2cccc(Nc3ncc(Cc4ccccc4)o3)c2C1>>OC1CCc2cccc(Nc3ncc(Cc4ccccc4)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-544195d3ef3c4d3499786c1c851a4cdb | CC(C)(C)C(=O)CBr.[N-]=[N+]=[N-]>>CC(C)(C)C(=O)CN=[N+]=[N-] | BrCC(C(C)(C)C)=O.[N-]=[N+]=[N-].[Na+]>>N(=[N+]=[N-])CC(C(C)(C)C)=O | Br[CH2:7][C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6].[N-:8]=[N+:9]=[N-:10]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[CH2:7][N:8]=[N+:9]=[N-:10] | CC(C)(C)C(=O)CBr.[N-]=[N+]=[N-] | CC(C)(C)C(=O)CN=[N+]=[N-] | null | null | CC(=O)C.[Cl-].[Na+].O | Heteroatom Alkylation and Arylation | OtherReaction | 7fe919211b759a1428a74cb1057710661d1d522f092678548e8299963d0e0365 | f47c52494d5e4df5ea8fcd9d0881525b7662fe98ccef006a42d77c12f4514758 | null | Br-[CH2;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[N-;H0;D1:5]=[#7;+:6]=[N;-;D1;H0:7]>>[C:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[N;H0;D2;+0:5]=[#7;+:6]=[N;-;D1;H0:7] | 100.3 | [{"value": 100.0, "product": "N(=[N+]=[N-])CC(C(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.3, "product": "N(=[N+]=[N-])CC(C(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 1-bromopinacolone (0.5 mL, 3.7 mmol) and NaN3 (0.48 g, 7.38 mmol) in 50 mL acetone was stirred overnight at room temperature. It was then poured into brine and extracted with dichloromethane. The extracts were washed with brine, were dried over Na2SO4, filtered, and were evaporated to afford the title comp... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Azide | null | null | null | Br- | CC(=O)C.[Cl-].[Na+].O | null | 8 | CC(C)(C)C(=O)CBr.[N-]=[N+]=[N-]>CC(=O)C.[Cl-].[Na+].O>CC(C)(C)C(=O)CN=[N+]=[N-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3a9cf539baa1435c99db87d2c335cae5 | CCOC1=CCc2cccc(Nc3ncc(C(C)(C)C)o3)c2C1>>CC(C)(C)c1cnc(Nc2cccc3c2CC(=O)CC3)o1 | C(C)(C)(C)C1=CN=C(O1)NC1=CC=CC=2CC=C(CC12)OCC.C(C)OC1=CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F>>C(C)(C)(C)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O | CC[O:18][C:17]1=[CH:19][CH2:20][c:14]2[cH:13][cH:12][cH:11][c:10]([NH:9][c:8]3[n:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[o:21]3)[c:15]2[CH2:16]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][n:7][c:8]([NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]3[c:15]2[CH2:16][C:17](=[O:18])[CH2:19][CH2:20]3)[o:21]1 | CCOC1=CCc2cccc(Nc3ncc(C(C)(C)C)o3)c2C1 | CC(C)(C)c1cnc(Nc2cccc3c2CC(=O)CC3)o1 | null | null | null | Miscellaneous | OtherReaction | 1a0269b029346ab05f1156601c24ee6b4906fe94a4a1e987a93732dd898a7bc6 | 06ee4e636755478860a38bbf5b67d3037b3b941f1ee50aea08d8ea3a7f23e056 | O=C1CCc2cccc(Nc3ncco3)c2C1 | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[c:5]:[c:6]-[C:7]-1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:7]-[c:6]:[c:5]-[C:4]-[CH2;D2;+0:3]-1 | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 1I, substituting the product of Example 17B for the product of Example 1H.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ketone | C1=CCc2ccccc2C1 | c1ccc2c(c1)CCCC2 | c1cocn1.c1ccc2c(c1)CCCC2 | Other | null | null | null | CCOC1=CCc2cccc(Nc3ncc(C(C)(C)C)o3)c2C1>>CC(C)(C)c1cnc(Nc2cccc3c2CC(=O)CC3)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c7fa47d9c0bd4364964ee29cc9ebb1e2 | CC(C)(C)c1cnc(Nc2cccc3c2CC(=O)CC3)o1>>CC(C)(C)c1cnc(Nc2cccc3c2CC(O)CC3)o1 | C(C)(C)(C)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O.FC(C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)=O)(F)F>>C(C)(C)(C)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)O | [CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][n:7][c:8]([NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]3[c:15]2[CH2:16][C:17](=[O:18])[CH2:19][CH2:20]3)[o:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][n:7][c:8]([NH:9][c:10]2[cH:11][cH:12][cH:13][c:14]3[c:15]2[CH2:16][CH:17]([OH:18])[CH2:19][CH2:20]3)[o:21]1 | CC(C)(C)c1cnc(Nc2cccc3c2CC(=O)CC3)o1 | CC(C)(C)c1cnc(Nc2cccc3c2CC(O)CC3)o1 | null | null | null | Reduction | Reduction of ketone to secondary alcohol | 3712a1f2cb52729543ec421b1a5b2fd3f779bad4223604244414834ade516040 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1cc2c(c(Nc3ncco3)c1)CCCC2 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[c:6]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[c:6] | null | [] | null | null | null | null | The title compound was prepared using the procedure as described in Example 2, substituting the product of Example 17C for the product of Example 1I. 1H NMR (DMSO-d6) δ 8.66 (s, 1H), 7.53 (d, J=7.8 Hz, 1H), 7.01 (t, J=7.8 Hz, 1H), 6.75 (d, J=7.5 Hz, 1H), 6.44 (s, 1H), 4.76 (d, J=3.7 Hz, 1H), 3.94 (m, 1H), 2.61-2.99 (m,... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1cocn1.c1ccc2c(c1)CCCC2 | null | null | null | null | CC(C)(C)c1cnc(Nc2cccc3c2CC(=O)CC3)o1>>CC(C)(C)c1cnc(Nc2cccc3c2CC(O)CC3)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8b411211982241daabf946e933b4fdea | CC(C)(C)[Si](C)(C)Cl.Nc1cccc2c1CC(O)CC2>>CC(C)(C)[Si](C)(C)OC1CCc2cccc(N)c2C1 | NC=1C=CC=C2CCC(CC12)O.C(C)(C)(C)[Si](C)(C)Cl.N1C=NC=C1>>[Si](C)(C)(C(C)(C)C)OC1CCC=2C=CC=C(C2C1)N | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH:9]1[CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][c:16]([NH2:17])[c:18]2[CH2:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]1[CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][c:16]([NH2:17])[c:18]2[CH2:19]1 | CC(C)(C)[Si](C)(C)Cl.Nc1cccc2c1CC(O)CC2 | CC(C)(C)[Si](C)(C)OC1CCc2cccc(N)c2C1 | null | null | ClCCl | Protection | Alcohol protection with silyl ethers | e19079a85b3e2f818dbb25a774b915f0e7349126f5b76d72c22f1c90edfa8480 | 16de9d9d08d1cc67ec96e76fc213a6b49c0af7979ac901a377ee705ba5071899 | c1ccc2c(c1)CCCC2 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9](-[OH;D1;+0:10])-[C:11]>>[C:8]-[C:9](-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7])-[C:11] | null | [] | null | null | null | null | A mixture of the product of Example 18A (2.33 g, 14.3 mmol), tert-butylchlorodimethylsilane (2.6 g, 17.2 mmol), and imidazole (2.9 g, 42.3 mmol) was stirred in 40 mL of dichloromethane at rt overnight. The mixture was then washed several times with water and once with brine. Drying over Na2SO4, filtered and evaporation... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccc2c(c1)CCCC2 | HCl | ClCCl | null | null | CC(C)(C)[Si](C)(C)Cl.Nc1cccc2c1CC(O)CC2>ClCCl>CC(C)(C)[Si](C)(C)OC1CCc2cccc(N)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-973473a85bce4c61ad758d2f94b5d00c | CC(C)(C)[Si](C)(C)OC1CCc2cccc(N)c2C1.S=C(Oc1ccccn1)Oc1ccccn1>>CC(C)(C)[Si](C)(C)OC1CCc2cccc(N=C=S)c2C1 | [Si](C)(C)(C(C)(C)C)OC1CCC=2C=CC=C(C2C1)N.C1=CC=NC(=C1)OC(=S)OC2=CC=CC=N2>>C(C)(C)(C)[Si](C)(C)OC1CC2=C(C=CC=C2CC1)N=C=S | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]1[CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][c:16]([NH2:17])[c:20]2[CH2:21]1.c1ccc(O[C:18](Oc2ccccn2)=[S:19])nc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]1[CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][c:16]([N:17]=[C:18]=[S:19])[c... | CC(C)(C)[Si](C)(C)OC1CCc2cccc(N)c2C1.S=C(Oc1ccccn1)Oc1ccccn1 | CC(C)(C)[Si](C)(C)OC1CCc2cccc(N=C=S)c2C1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | 9a80968abe70879a9369740fc6263b884e7d64cc7f090788997500a3069df240 | 0bc85fa9e96d94388afe13d389361cafe3d77a7182964e359eefb70b6e8160bc | c1ccc2c(c1)CCCC2 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:5]=[C;H0;D3;+0:6](-O-c1:c:c:c:c:n:1)-O-c1:c:c:c:c:n:1>>[S;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | 72 | [{"value": 72.0, "product": "C(C)(C)(C)[Si](C)(C)OC1CC2=C(C=CC=C2CC1)N=C=S", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the product of Example 18B, 2-(tert-butyldimethylsilyl)-ol (1.4 g, 5.07 mmol) and di-2-pyridyl thionocarbonate (1.07 g, 4.61 mmol) in 30 mL dichloromethane was stirred at room temperature overnight. The mixture was evaporated, then the residue was taken up in 2 mL dichloromethane and filtered through sili... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine.Thiocarbonyl | Isothiocyanate | c1ccncc1.c1ccncc1 | null | c1ccc2c(c1)CCCC2 | HO- | ClCCl | null | null | CC(C)(C)[Si](C)(C)OC1CCc2cccc(N)c2C1.S=C(Oc1ccccn1)Oc1ccccn1>ClCCl>CC(C)(C)[Si](C)(C)OC1CCc2cccc(N=C=S)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c31e6070c6924d6d88a783bf76eea8cc | CC(C)(C)[Si](C)(C)OC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1.CI>>CN(c1ncc(-c2ccc(C(F)(F)F)cc2)o1)c1cccc2c1CC(O[Si](C)(C)C(C)(C)C)CC2 | C(C)(=O)OCC.IC.[Si](C)(C)(C(C)(C)C)OC1CCC=2C=CC=C(C2C1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F.[H-].[Na+]>>[Si](C)(C)(C(C)(C)C)OC1CCC=2C=CC=C(C2C1)N(C=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F)C | [NH:2]([c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[o:17]1)[c:18]1[cH:19][cH:20][cH:21][c:22]2[c:23]1[CH2:24][CH:25]([O:26][Si:27]([CH3:28])([CH3:29])[C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34][CH2:35]2.I[CH3:1]>>[CH3:1][N:2]([c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c... | CC(C)(C)[Si](C)(C)OC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1.CI | CN(c1ncc(-c2ccc(C(F)(F)F)cc2)o1)c1cccc2c1CC(O[Si](C)(C)C(C)(C)C)CC2 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e1587a52a1bca6a80c6048d43276d8bccf8d3e94e692e6b210e5fd3b22494187 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | I-[CH3;D1;+0:1].[c:2]:[c:3](-[NH;D2;+0:4]-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[#8;a:9]:1):[c:10]>>[CH3;D1;+0:1]-[N;H0;D3;+0:4](-[c:3](:[c:2]):[c:10])-[c:5]1:[#7;a:6]:[c:7]:[c:8]:[#8;a:9]:1 | 18 | [{"value": 18.0, "product": "[Si](C)(C)(C(C)(C)C)OC1CCC=2C=CC=C(C2C1)N(C=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | The product of Example 18D (300 mg, 0.615 mmol) in 5 mL N,N-dimethylformamide was treated with NaH (60% dispersion, 32 mg, 0.8 mmol) at rt. After stirring for 5 minutes, iodomethane (0.15 mL, 2.4 mmol) was added. The reaction was stirred at rt for 24 h, then it was poured into ethyl acetate and washed several times wit... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | null | null | c1cocn1.c1ccccc1.c1ccc2c(c1)CCCC2 | HI | CN(C=O)C | null | 0.083333 | CC(C)(C)[Si](C)(C)OC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1.CI>CN(C=O)C>CN(c1ncc(-c2ccc(C(F)(F)F)cc2)o1)c1cccc2c1CC(O[Si](C)(C)C(C)(C)C)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72ae43375b92458aa55315b89e4ff103 | CN(c1ncc(-c2ccc(C(F)(F)F)cc2)o1)c1cccc2c1CC(O[Si](C)(C)C(C)(C)C)CC2>>CN(c1ncc(-c2ccc(C(F)(F)F)cc2)o1)c1cccc2c1CC(O)CC2 | [Si](C)(C)(C(C)(C)C)OC1CCC=2C=CC=C(C2C1)N(C=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F)C.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>CN(C=1C=CC=C2CCC(CC12)O)C=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F | CC(C)(C)[Si](C)(C)[O:26][CH:25]1[CH2:24][c:23]2[c:18]([N:2]([CH3:1])[c:3]3[n:4][cH:5][c:6](-[c:7]4[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]4)[o:17]3)[cH:19][cH:20][cH:21][c:22]2[CH2:28][CH2:27]1>>[CH3:1][N:2]([c:3]1[n:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:1... | CN(c1ncc(-c2ccc(C(F)(F)F)cc2)o1)c1cccc2c1CC(O[Si](C)(C)C(C)(C)C)CC2 | CN(c1ncc(-c2ccc(C(F)(F)F)cc2)o1)c1cccc2c1CC(O)CC2 | null | null | O1CCCC1 | Deprotection | Alcohol deprotection from silyl ethers | 050b4fb4e1e9936189860d27dded10ae70a294a642c52f800eb9d5aaef7955cc | 88623e19d23cdfe8e1a4c167fd6cfc51d774a1c784b87a7bb2df8153ee93e67a | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[OH;D1;+0:1])-[C:4] | 62.1 | [{"value": 62.0, "product": "CN(C=1C=CC=C2CCC(CC12)O)C=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.1, "product": "CN(C=1C=CC=C2CCC(CC12)O)C=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of the product of Example 18E (56 mg, 0.112 mmol) in 6 mL of tetrahydrofuran was treated with a solution of tetrabutylammonium fluoride (1M-in-tetrahydrofuran, 1 mL, 1 mmol). The reaction mixture was stirred at rt for 4 h, then the solvent was evaporated, and the residue was chromatographed on silica gel, el... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Secondary alcohol | null | null | c1cocn1.c1ccccc1.c1ccc2c(c1)CCCC2 | Other | O1CCCC1 | null | 4 | CN(c1ncc(-c2ccc(C(F)(F)F)cc2)o1)c1cccc2c1CC(O[Si](C)(C)C(C)(C)C)CC2>O1CCCC1>CN(c1ncc(-c2ccc(C(F)(F)F)cc2)o1)c1cccc2c1CC(O)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-23d745707ea149d9b42a53d049222d2e | CC(=O)OC(C)=O.CC(C)(C)c1ccc(-c2cnc(Nc3cccc4c3CC(O)CC4)o2)cc1>>CC(=O)N(c1ncc(-c2ccc(C(C)(C)C)cc2)o1)c1cccc2c1CC(O)CC2 | C(C)(C)(C)C1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)O.C(C)(=O)OC(C)=O.C(C)N(CC)CC>>C(C)(C)(C)C1=CC=C(C=C1)C1=CN=C(O1)N(C(C)=O)C1=CC=CC=2CCC(CC12)O | CC(=O)O[C:2]([CH3:1])=[O:3].[NH:4]([c:5]1[n:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]2)[o:19]1)[c:20]1[cH:21][cH:22][cH:23][c:24]2[c:25]1[CH2:26][CH:27]([OH:28])[CH2:29][CH2:30]2>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[n:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([CH3:1... | CC(=O)OC(C)=O.CC(C)(C)c1ccc(-c2cnc(Nc3cccc4c3CC(O)CC4)o2)cc1 | CC(=O)N(c1ncc(-c2ccc(C(C)(C)C)cc2)o1)c1cccc2c1CC(O)CC2 | null | null | O1CCCC1.C(C)(=O)OCC | Acylation | Aminolysis of esters | 72a6d1966b6b15ac7195d4682af251dc9ffac857f784a4242970ab5c7a529369 | 6593c6062585994f02076cd3c86920ae7244b86659eab65c21b5a8628c6d4bb8 | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5](-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1):[c:12]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:6](-[c:5](:[c:4]):[c:12])-[c:7]1:[#7;a:8]:[c:9]:[c:10]:[#8;a:11]:1 | 45 | [{"value": 45.0, "product": "C(C)(C)(C)C1=CC=C(C=C1)C1=CN=C(O1)N(C(C)=O)C1=CC=CC=2CCC(CC12)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.7, "product": "C(C)(C)(C)C1=CC=C(C=C1)C1=CN=C(O1)N(C(C)=O)C1=CC=CC=2CCC(CC12)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The product of Example 3C (76 mg, 0.21 mmol) in 2 mL tetrahydrofuran was stirred with acetic anhydride (0.026 mL, 0.275 mmol) and triethylamine (0.088 mL, 0.63 mmol) at rt for 3 h. The reaction mixture was then diluted with ethyl acetate and washed with water and brine. The organic phase was dried over Na2SO4, filtered... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amine | Tertiary amide | null | null | c1cocn1.c1ccccc1.c1ccc2c(c1)CCCC2 | HO- | O1CCCC1.C(C)(=O)OCC | null | null | CC(=O)OC(C)=O.CC(C)(C)c1ccc(-c2cnc(Nc3cccc4c3CC(O)CC4)o2)cc1>O1CCCC1.C(C)(=O)OCC>CC(=O)N(c1ncc(-c2ccc(C(C)(C)C)cc2)o1)c1cccc2c1CC(O)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4df698c782f74511acf0e9ef72fa6cfb | CC(C)(C)[Si](C)(C)OC1CCc2cccc(N)c2C1.O=C(Cl)OCc1ccccc1>>O=C(Nc1cccc2c1CC(O)CC2)OCc1ccccc1 | C(C1=CC=CC=C1)OC(=O)Cl.[Si](C)(C)(C(C)(C)C)OC1CCC=2C=CC=C(C2C1)N.C(C)(C)N(CC)C(C)C>>C(C1=CC=CC=C1)OC(NC1=CC=CC=2CCC(CC12)O)=O | CC(C)(C)[Si](C)(C)[O:12][CH:11]1[CH2:10][c:9]2[c:4]([NH2:3])[cH:5][cH:6][cH:7][c:8]2[CH2:14][CH2:13]1.Cl[C:2](=[O:1])[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][c:8]2[c:9]1[CH2:10][CH:11]([OH:12])[CH2:13][CH2:14]2)[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21... | CC(C)(C)[Si](C)(C)OC1CCc2cccc(N)c2C1.O=C(Cl)OCc1ccccc1 | O=C(Nc1cccc2c1CC(O)CC2)OCc1ccccc1 | null | null | C(Cl)Cl | Protection | OtherReaction | 7a72cbf121ba675f0cecdef5b49e9b56603d9fb0a1cf0df901c5c50d27850c76 | c7adefa28b4f88b0e979fcb711af2761ecd5e569d557ede433b7717230eaf899 | O=C(Nc1cccc2c1CCCC2)OCc1ccccc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]-[c:5]:[c:6](-[NH2;D1;+0:7]):[c:8].Cl-[C;H0;D3;+0:9](=[O;D1;H0:10])-[#8:11]-[C:12]>>[C:3]-[C:2](-[OH;D1;+0:1])-[C:4]-[c:5]:[c:6](-[NH;D2;+0:7]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[#8:11]-[C:12]):[c:8] | 99.5 | [{"value": 99.5, "product": "C(C1=CC=CC=C1)OC(NC1=CC=CC=2CCC(CC12)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | Benzylchloroformate (6.96 g, 40.8 mmol) was added dropwise to a solution of Example 18B (10.3 g, 37.1 mmol,) and diisopropylethylamine (7.20 g, 55.7 mmol) in 120 mL CH2Cl2 at 0° C. The mixture was stirred for 18 hours gradually warming to ambient temperature after which the volatiles were evaporated under reduced press... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine.TMS ether protective group | Carbamic ester.Ether.Secondary alcohol | null | null | c1ccc2c(c1)CCCC2.c1ccccc1 | HCl | C(Cl)Cl | null | 18 | CC(C)(C)[Si](C)(C)OC1CCc2cccc(N)c2C1.O=C(Cl)OCc1ccccc1>C(Cl)Cl>O=C(Nc1cccc2c1CC(O)CC2)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-06edc073ef404cf997477c31844ab0dc | [N-]=[N+]=NC1CCc2cccc(NC(=O)OCc3ccccc3)c2C1>>NC1CCc2cccc(NC(=O)OCc3ccccc3)c2C1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C1=CC=CC=C1)OC(NC1=CC=CC=2CCC(CC12)N=[N+]=[N-])=O.O>>C(C1=CC=CC=C1)OC(NC1=CC=CC=2CCC(CC12)N)=O | [N-]=[N+]=[N:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]2[CH2:22]1>>[NH2:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]2[CH2:22]1 | [N-]=[N+]=NC1CCc2cccc(NC(=O)OCc3ccccc3)c2C1 | NC1CCc2cccc(NC(=O)OCc3ccccc3)c2C1 | null | null | C1CCOC1 | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=C(Nc1cccc2c1CCCC2)OCc1ccccc1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[N+]=[N-])-[C:4]>>[C:1]-[C:2](-[NH2;D1;+0:3])-[C:4] | 84.4 | [{"value": 83.0, "product": "C(C1=CC=CC=C1)OC(NC1=CC=CC=2CCC(CC12)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.4, "product": "C(C1=CC=CC=C1)OC(NC1=CC=CC=2CCC(CC12)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | Polymer supported triphenylphosphine (9.5 g, 28 mmol) was added to the product of Example 20B (4.6 g, 14 mmol) in THF (100 mL) containing 1.3 g (71 mmol) H2O. The mixture was stirred for 48 hours at ambient temperature, then diluted with THF and filtered through a pad of celite. The filter cake was washed with 3 solven... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccc2c(c1)CCCC2.c1ccccc1 | Other | C1CCOC1 | null | 48 | [N-]=[N+]=NC1CCc2cccc(NC(=O)OCc3ccccc3)c2C1>C1CCOC1>NC1CCc2cccc(NC(=O)OCc3ccccc3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-61106ec27caa41878b6dc1c4c80983f5 | CC(C)(C)OC(=O)NC1CCc2cccc(N=C=S)c2C1.Cc1ccc(C(=O)CN=[N+]=[N-])cc1>>Cc1ccc(-c2cnc(Nc3cccc4c3CC(NC(=O)OC(C)(C)C)CC4)o2)cc1 | N(=[N+]=[N-])CC(=O)C1=CC=C(C=C1)C(F)(F)F.C(C)(C)(C)OC(NC1CC2=C(C=CC=C2CC1)N=C=S)=O.C(C)OC=1CC2=C(C=CC=C2CC1)N=C=S.N(=[N+]=[N-])CC(=O)C1=CC=C(C=C1)C>>C(C)(C)(C)OC(NC1CC2=C(C=CC=C2CC1)NC=1OC(=CN1)C1=CC=C(C=C1)C)=O | S=[C:9]=[N:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]1[CH2:17][CH:18]([NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:27][CH2:28]2.[N-]=[N+]=[N:8][CH2:7][C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:31][cH:30]1)=[O:29]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13... | CC(C)(C)OC(=O)NC1CCc2cccc(N=C=S)c2C1.Cc1ccc(C(=O)CN=[N+]=[N-])cc1 | Cc1ccc(-c2cnc(Nc3cccc4c3CC(NC(=O)OC(C)(C)C)CC4)o2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 308925f177354ae8700ee398a7647aaf489213eaacf0ba5850c303e603a910c8 | fff1fecf10f43f7b7b2f4a1a42805992525d7d039d15ced016ce6eb268a00bed | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[N-]=[N+]=[N;H0;D2;+0:6]-[CH2;D2;+0:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:4]:[c:3](-[NH;D2;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[o;H0;D2;+0:9]:1)... | 83 | [{"value": 83.0, "product": "C(C)(C)(C)OC(NC1CC2=C(C=CC=C2CC1)NC=1OC(=CN1)C1=CC=C(C=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.9, "product": "C(C)(C)(C)OC(NC1CC2=C(C=CC=C2CC1)NC=1OC(=CN1)C1=CC=C(C=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared using the procedure as described in Example 1H, substituting the product of Example 20F (188 mg, 0.618 mmol) for the product of Example 1F and the product of Example 9A (130 mg, 0.741 mmol) for the product of Example 1G. The crude product was purified by flash chromatography eluting with... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Azide.Isothiocyanate | Secondary amine | null | c1cocn1 | c1ccccc1.c1cocn1.c1ccc2c(c1)CCCC2 | Other | null | null | null | CC(C)(C)OC(=O)NC1CCc2cccc(N=C=S)c2C1.Cc1ccc(C(=O)CN=[N+]=[N-])cc1>>Cc1ccc(-c2cnc(Nc3cccc4c3CC(NC(=O)OC(C)(C)C)CC4)o2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cc026df84b014b2786546b5466938416 | Cc1ccc(-c2cnc(Nc3cccc4c3CC(NC(=O)OC(C)(C)C)CC4)o2)cc1>>Cc1ccc(-c2cnc(Nc3cccc4c3CC(N)CC4)o2)cc1 | Cl.C(C)(C)(C)OC(NC1CC2=C(C=CC=C2CC1)NC=1OC(=CN1)C1=CC=C(C=C1)C)=O>>CC1=CC=C(C=C1)C1=CN=C(O1)NC1=CC=CC=2CCC(CC12)N | CC(C)(C)OC(=O)[NH:19][CH:18]1[CH2:17][c:16]2[c:11]([NH:10][c:9]3[n:8][cH:7][c:6](-[c:5]4[cH:4][cH:3][c:2]([CH3:1])[cH:24][cH:23]4)[o:22]3)[cH:12][cH:13][cH:14][c:15]2[CH2:21][CH2:20]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[CH2:17][CH:18]([NH2:19])[CH2:2... | Cc1ccc(-c2cnc(Nc3cccc4c3CC(NC(=O)OC(C)(C)C)CC4)o2)cc1 | Cc1ccc(-c2cnc(Nc3cccc4c3CC(N)CC4)o2)cc1 | null | null | O1CCOCC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | 45 | MINUTE | Hydrogen chloride in dioxane (4N, 7 mL, 28 mmol) was added to a suspension of 199 mg (0.474 mmol) of the product of Example 20G in 1 mL dioxane. After stirring 45 minutes, the mixture was quenched with 3N NaOH solution, then diluted with EtOAc and poured into water. The separated organic phase was washed with brine, dr... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1cocn1.c1ccc2c(c1)CCCC2 | HO- | O1CCOCC1 | null | 0.75 | Cc1ccc(-c2cnc(Nc3cccc4c3CC(NC(=O)OC(C)(C)C)CC4)o2)cc1>O1CCOCC1>Cc1ccc(-c2cnc(Nc3cccc4c3CC(N)CC4)o2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bbb72222bfc9488f83a78ce1022ac17a | CC(C)(C)OC(=O)NC1CCc2cccc(N=C=S)c2C1.[N-]=[N+]=NCC(=O)c1ccc(C(F)(F)F)cc1>>CC(C)(C)OC(=O)NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 | C(C)(C)(C)OC(NC1CC2=C(C=CC=C2CC1)N=C=S)=O.C(C)OC=1CC2=C(C=CC=C2CC1)N=C=S.N(=[N+]=[N-])CC(=O)C1=CC=C(C=C1)C(F)(F)F>>C(C)(C)(C)OC(NC1CC2=C(C=CC=C2CC1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F)=O | S=[C:18]=[N:17][c:16]1[cH:15][cH:14][cH:13][c:12]2[c:33]1[CH2:34][CH:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][CH2:11]2.[N-]=[N+]=[N:19][CH2:20][C:21]([c:22]1[cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30][cH:31]1)=[O:32]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[... | CC(C)(C)OC(=O)NC1CCc2cccc(N=C=S)c2C1.[N-]=[N+]=NCC(=O)c1ccc(C(F)(F)F)cc1 | CC(C)(C)OC(=O)NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 308925f177354ae8700ee398a7647aaf489213eaacf0ba5850c303e603a910c8 | fff1fecf10f43f7b7b2f4a1a42805992525d7d039d15ced016ce6eb268a00bed | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[N-]=[N+]=[N;H0;D2;+0:6]-[CH2;D2;+0:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:4]:[c:3](-[NH;D2;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[o;H0;D2;+0:9]:1)... | 37 | [{"value": 37.0, "product": "C(C)(C)(C)OC(NC1CC2=C(C=CC=C2CC1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.8, "product": "C(C)(C)(C)OC(NC1CC2=C(C=CC=C2CC1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared using the procedure as described in Example 1H, substituting the product of Example 20F (215 mg, 0.706 mmol) for the product of Example 1F, and the product of Example 1G (194 mg, 0.848 mmol). The crude product was purified by flash chromatography eluting with 20% EtOAc/hexane which gave ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Azide.Isothiocyanate | Secondary amine | null | c1cocn1 | c1ccc2c(c1)CCCC2.c1cocn1.c1ccccc1 | Other | null | null | null | CC(C)(C)OC(=O)NC1CCc2cccc(N=C=S)c2C1.[N-]=[N+]=NCC(=O)c1ccc(C(F)(F)F)cc1>>CC(C)(C)OC(=O)NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-821a060f8c434154a296276dd9d3588a | CC(C)(C)OC(=O)NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1>>NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 | C(C)(C)(C)OC(NC1CC2=C(C=CC=C2CC1)NC=1OC(=CN1)C1=CC=C(C=C1)C(F)(F)F)=O.C(C)(C)(C)OC(NC1CC2=C(C=CC=C2CC1)NC=1OC(=CN1)C1=CC=C(C=C1)C)=O>>FC(C1=CC=C(C=C1)C1=CN=C(O1)NC1=CC=CC=2CCC(CC12)N)(F)F | CC(C)(C)OC(=O)[NH:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]4)[o:25]3)[c:26]2[CH2:27]1>>[NH2:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][... | CC(C)(C)OC(=O)NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 | NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | 38.1 | [{"value": 38.0, "product": "FC(C1=CC=C(C=C1)C1=CN=C(O1)NC1=CC=CC=2CCC(CC12)N)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.1, "product": "FC(C1=CC=C(C=C1)C1=CN=C(O1)NC1=CC=CC=2CCC(CC12)N)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared using the procedure as described in Example 20H substituting the product of Example 21A (120 mg, 0.253 mmol) for the product of Example 20G. The crude product was purified by trituration with Et2O/hexanes which resulted in 36 mg (38%) of the title compound as a white solid. 1H NMR (DMSO-... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)CCCC2.c1cocn1.c1ccccc1 | HO- | null | null | null | CC(C)(C)OC(=O)NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1>>NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f927a438a17c4009a39ffd4602a2c56e | CC(C)(C)OC(=O)NC1CCc2cccc(N=C=S)c2C1.[N-]=[N+]=NCC(=O)c1ccc(C(F)(F)F)cc1F>>CC(C)(C)OC(=O)NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4F)o3)c2C1 | N(=[N+]=[N-])CC(=O)C1=CC=C(C=C1)C(F)(F)F.C(C)(C)(C)OC(NC1CC2=C(C=CC=C2CC1)N=C=S)=O.C(C)OC=1CC2=C(C=CC=C2CC1)N=C=S.N(=[N+]=[N-])CC(=O)C1=C(C=C(C=C1)C(F)(F)F)F>>C(C)(C)(C)OC(NC1CC2=C(C=CC=C2CC1)NC=1OC(=CN1)C1=C(C=C(C=C1)C(F)(F)F)F)=O | S=[C:18]=[N:17][c:16]1[cH:15][cH:14][cH:13][c:12]2[c:34]1[CH2:35][CH:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:10][CH2:11]2.[N-]=[N+]=[N:19][CH2:20][C:21]([c:22]1[cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30][c:31]1[F:32])=[O:33]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH... | CC(C)(C)OC(=O)NC1CCc2cccc(N=C=S)c2C1.[N-]=[N+]=NCC(=O)c1ccc(C(F)(F)F)cc1F | CC(C)(C)OC(=O)NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4F)o3)c2C1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 308925f177354ae8700ee398a7647aaf489213eaacf0ba5850c303e603a910c8 | fff1fecf10f43f7b7b2f4a1a42805992525d7d039d15ced016ce6eb268a00bed | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[F;D1;H0:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[CH2;D2;+0:12]-[N;H0;D2;+0:13]=[N+]=[N-]):[c:14]:[c:15]>>[F;D1;H0:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](-[c;H0;D3;+0:10]1:[cH;D2;+0:12]:[n;H0;D2;+0:13]:[c;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3](:[c:4]):[c:... | 16 | [{"value": 16.0, "product": "C(C)(C)(C)OC(NC1CC2=C(C=CC=C2CC1)NC=1OC(=CN1)C1=C(C=C(C=C1)C(F)(F)F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.0, "product": "C(C)(C)(C)OC(NC1CC2=C(C=CC=C2CC1)NC=1OC(=CN1)C1=C(C=C(C=C1)C(F)(F)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared using the procedure as described in Example 1H, substituting the product of Example 20F (415 mg, 1.36 mmol) for the product of Example 1F and the product of Example 22A (404 mg, 1.63 mmol) for the product of Example 1G. The crude product was purified by flash chromatography eluting with ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Azide.Isothiocyanate | Secondary amine | null | c1cocn1 | c1ccc2c(c1)CCCC2.c1cocn1.c1ccccc1 | Other | null | null | null | CC(C)(C)OC(=O)NC1CCc2cccc(N=C=S)c2C1.[N-]=[N+]=NCC(=O)c1ccc(C(F)(F)F)cc1F>>CC(C)(C)OC(=O)NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4F)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cb420747152046439dfc72ae869b1f80 | CC(C)(C)OC(=O)NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4F)o3)c2C1>>NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4F)o3)c2C1 | I[Si](C)(C)C.C(C)(C)(C)OC(NC1CC2=C(C=CC=C2CC1)NC=1OC(=CN1)C1=C(C=C(C=C1)C(F)(F)F)F)=O>>FC1=C(C=CC(=C1)C(F)(F)F)C1=CN=C(O1)NC1=CC=CC=2CCC(CC12)N | CC(C)(C)OC(=O)[NH:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][c:24]4[F:25])[o:26]3)[c:27]2[CH2:28]1>>[NH2:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH... | CC(C)(C)OC(=O)NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4F)o3)c2C1 | NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4F)o3)c2C1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | 15 | MINUTE | Iodotrimethylsilane (52 mg, 0.260 mmol) was added dropwise to a solution of the product of Example 22B (107 mg, 0.218 mmol) in 1 mL CH2Cl2 at ambient temperature. After 15 minutes the reaction was diluted with CH2Cl2 and quenched with 1N aq NaOH solution. The mixture was stirred 15 minutes and then poured into water. T... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)CCCC2.c1cocn1.c1ccccc1 | HO- | C(Cl)Cl | null | 0.25 | CC(C)(C)OC(=O)NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4F)o3)c2C1>C(Cl)Cl>NC1CCc2cccc(Nc3ncc(-c4ccc(C(F)(F)F)cc4F)o3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a9be4f51300d46839baae8233fdcaff6 | CS(=O)(=O)Cl.NC1CCc2cccc(NC(=O)OCc3ccccc3)c2C1>>CS(=O)(=O)NC1CCc2cccc(NC(=O)OCc3ccccc3)c2C1 | O.CS(=O)(=O)Cl.C(C1=CC=CC=C1)OC(NC1=CC=CC=2CCC(CC12)N)=O.C(C)(C)N(CC)C(C)C>>C(C1=CC=CC=C1)OC(NC1=CC=CC=2CCC(CC12)NS(=O)(=O)C)=O | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[NH2:5][CH:6]1[CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[O:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:25]2[CH2:26]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][CH:6]1[CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[O:17][CH2:18][c:1... | CS(=O)(=O)Cl.NC1CCc2cccc(NC(=O)OCc3ccccc3)c2C1 | CS(=O)(=O)NC1CCc2cccc(NC(=O)OCc3ccccc3)c2C1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(Nc1cccc2c1CCCC2)OCc1ccccc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6](-[NH2;D1;+0:7])-[C:8]>>[C:5]-[C:6](-[NH;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:8] | 58.2 | [{"value": 58.0, "product": "C(C1=CC=CC=C1)OC(NC1=CC=CC=2CCC(CC12)NS(=O)(=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.2, "product": "C(C1=CC=CC=C1)OC(NC1=CC=CC=2CCC(CC12)NS(=O)(=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Methanesulfonyl chloride (176 mg, 1.54 mmol) was added dropwise to a solution of the product from Example 20C (381 mg, 1.29 mmol) and diisopropylethylamine (332 mg, 2.57 mmol) in 15 mL CH2Cl2 at ambient temperature. The mixture was stirred 30 minutes, diluted with methylene chloride and poured into water. The separated... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2c(c1)CCCC2.c1ccccc1 | HCl | C(Cl)Cl | null | 0.5 | CS(=O)(=O)Cl.NC1CCc2cccc(NC(=O)OCc3ccccc3)c2C1>C(Cl)Cl>CS(=O)(=O)NC1CCc2cccc(NC(=O)OCc3ccccc3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-69076bdd4b02416c8e9fe9ea490d68a5 | CS(=O)(=O)NC1CCc2cccc(NC(=O)OCc3ccccc3)c2C1>>CS(=O)(=O)NC1CCc2cccc(N)c2C1 | C(C1=CC=CC=C1)OC(NC1=CC=CC=2CCC(CC12)NS(=O)(=O)C)=O>>NC=1C=CC=C2CCC(CC12)NS(=O)(=O)C | O=C(OCc1ccccc1)[NH:14][c:13]1[cH:12][cH:11][cH:10][c:9]2[c:15]1[CH2:16][CH:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[CH2:7][CH2:8]2>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][CH:6]1[CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][c:13]([NH2:14])[c:15]2[CH2:16]1 | CS(=O)(=O)NC1CCc2cccc(NC(=O)OCc3ccccc3)c2C1 | CS(=O)(=O)NC1CCc2cccc(N)c2C1 | null | null | CO.C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | c1ccc2c(c1)CCCC2 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 72 | [{"value": 72.0, "product": "NC=1C=CC=C2CCC(CC12)NS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.8, "product": "NC=1C=CC=C2CCC(CC12)NS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared using the procedure as described in Example 20E substituting the product of Example 23A (280 mg, 0.748 mmol) for the product Example 20D. Flash chromatography (5% to 10% CH3OH/CH2Cl2) gave 129 mg (72%) of the title compound as a white solid. 1H NMR (DMSO-d6) δ 7.20 (d, J=7.5 Hz, 1H), 6.7... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1ccc2c(c1)CCCC2 | HO- | CO.C(Cl)Cl | null | null | CS(=O)(=O)NC1CCc2cccc(NC(=O)OCc3ccccc3)c2C1>CO.C(Cl)Cl>CS(=O)(=O)NC1CCc2cccc(N)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4ca613d4c76f43b0a96578213c5ac505 | CS(=O)(=O)NC1CCc2cccc(N=C=S)c2C1.Cc1ccc(C(=O)CN=[N+]=[N-])cc1>>Cc1ccc(-c2cnc(Nc3cccc4c3CC(NS(C)(=O)=O)CC4)o2)cc1 | N(=[N+]=[N-])CC(=O)C1=CC=C(C=C1)C(F)(F)F.N(=C=S)C=1C=CC=C2CCC(CC12)NS(=O)(=O)C.C(C)OC=1CC2=C(C=CC=C2CC1)N=C=S.N(=[N+]=[N-])CC(=O)C1=CC=C(C=C1)C>>CC1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)NS(=O)(=O)C | S=[C:9]=[N:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[c:16]1[CH2:17][CH:18]([NH:19][S:20]([CH3:21])(=[O:22])=[O:23])[CH2:24][CH2:25]2.[N-]=[N+]=[N:8][CH2:7][C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:28][cH:27]1)=[O:26]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[... | CS(=O)(=O)NC1CCc2cccc(N=C=S)c2C1.Cc1ccc(C(=O)CN=[N+]=[N-])cc1 | Cc1ccc(-c2cnc(Nc3cccc4c3CC(NS(C)(=O)=O)CC4)o2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 308925f177354ae8700ee398a7647aaf489213eaacf0ba5850c303e603a910c8 | fff1fecf10f43f7b7b2f4a1a42805992525d7d039d15ced016ce6eb268a00bed | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)o2)cc1 | S=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[N-]=[N+]=[N;H0;D2;+0:6]-[CH2;D2;+0:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[c:4]:[c:3](-[NH;D2;+0:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[o;H0;D2;+0:9]:1)... | 64.4 | [{"value": 64.0, "product": "CC1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)NS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.4, "product": "CC1=CC=C(C=C1)C1=CN=C(O1)NC=1C=CC=C2CCC(CC12)NS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared using the procedure as described in Example 1H, substituting the product of Example 23C (128 mg, 0.453 mmol) for the product of Example 1F and the product of Example 9A (95 mg, 0.544 mmol) for the product of Example 1G. The crude product was purified by flash chromatography eluting with ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Azide.Isothiocyanate | Secondary amine | null | c1cocn1 | c1ccccc1.c1cocn1.c1ccc2c(c1)CCCC2 | Other | null | null | null | CS(=O)(=O)NC1CCc2cccc(N=C=S)c2C1.Cc1ccc(C(=O)CN=[N+]=[N-])cc1>>Cc1ccc(-c2cnc(Nc3cccc4c3CC(NS(C)(=O)=O)CC4)o2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bdc3ee4fcf224c9cafaaaedd1562b4f3 | CC(C)(C)[Si](C)(C)OC1CCc2cccc(N=C=S)c2C1.N>>CC(C)(C)[Si](C)(C)OC1CCc2cccc(NC(N)=S)c2C1 | C(C)(C)(C)[Si](C)(C)OC1CC2=C(C=CC=C2CC1)N=C=S.N>>[Si](C)(C)(C(C)(C)C)OC1CCC=2C=CC=C(C2C1)NC(=S)N | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]1[CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][c:16]([N:17]=[C:18]=[S:20])[c:21]2[CH2:22]1.[NH3:19]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]1[CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][c:16]([NH:17][C:18]([NH2:19])=[S:20])[c:21]2... | CC(C)(C)[Si](C)(C)OC1CCc2cccc(N=C=S)c2C1.N | CC(C)(C)[Si](C)(C)OC1CCc2cccc(NC(N)=S)c2C1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 9ea44f258f40d07ea72818ac0d167217e6d11d32357aad8e81d4f079b5cbad85 | 8a79caa9356d3b30a3b61a9504f2b151cec34b3b4ac7afcdd36f0060d08e7701 | c1ccc2c(c1)CCCC2 | [NH3;D0;+0:1].[S;D1;H0:2]=[C;H0;D2;+0:3]=[N;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[NH2;D1;+0:1]-[C;H0;D3;+0:3](=[S;D1;H0:2])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 6 | HOUR | A solution of the product of Example 18C (1.25 g, 3.91 mmol) in THF (50 mL) was treated with 7N methanolic NH3 (5.6 mL, 39.1 mmol), and the mixture was stirred at room temperature for 6 hours. The mixture was partitioned between EtOAc and H2O, and the separated organic phase was washed with brine, dried over Na2SO4, fi... | 10.6084/m9.figshare.5104873.v1 | null | Isothiocyanate | Thiourea | null | null | c1ccc2c(c1)CCCC2 | null | C1CCOC1 | null | 6 | CC(C)(C)[Si](C)(C)OC1CCc2cccc(N=C=S)c2C1.N>C1CCOC1>CC(C)(C)[Si](C)(C)OC1CCc2cccc(NC(N)=S)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-437a814e1d3a49be80a33c254539f270 | CC(C)(C)[Si](C)(C)OC1CCc2cccc(NC(N)=S)c2C1.COC(OC)C(Br)c1ccccc1>>OC1CCc2cccc(Nc3ncc(-c4ccccc4)s3)c2C1 | [Si](C)(C)(C(C)(C)C)OC1CCC=2C=CC=C(C2C1)NC(=S)N.BrC(C(OC)OC)C1=CC=CC=C1>>C1(=CC=CC=C1)C1=CN=C(S1)NC=1C=CC=C2CCC(CC12)O | CC(C)(C)[Si](C)(C)[O:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][C:11]([NH2:12])=[S:21])[c:22]2[CH2:23]1.CO[CH:13](OC)[CH:14](Br)[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[OH:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][c... | CC(C)(C)[Si](C)(C)OC1CCc2cccc(NC(N)=S)c2C1.COC(OC)C(Br)c1ccccc1 | OC1CCc2cccc(Nc3ncc(-c4ccccc4)s3)c2C1 | null | null | Cl.CCO | Aromatic Heterocycle Formation | OtherReaction | a2bf14450b0dd3ceddf6727a9aa61ffed1bda6fceb69f3f5422c9bb90a172409 | 8988896a8635cb38cf035f5417195a7feb1a96e162d0f78b7e461c01ad2d74f7 | c1ccc(-c2cnc(Nc3cccc4c3CCCC4)s2)cc1 | Br-[CH;D3;+0:1](-[CH;D3;+0:2](-O-C)-O-C)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:8]-[C:9](-[C:10])-[C:11].[NH2;D1;+0:12]-[C;H0;D3;+0:13](=[S;H0;D1;+0:14])-[#7:15]-[c:16]>>[C:10]-[C:9](-[OH;D1;+0:8])-[C:11].[c:5]:[c:4]:[c;H0;D3;+0:3](-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[n;H0;D2;+0:12]:[c;... | null | [] | null | null | null | null | A mixture of the product of Example 24A (200 mg, 0.594 mmol) and the product of Example 24B (146 mg, 0.596 mmol) was refluxed for 2 hours in a mixture of EtOH (6 mL) and 1N HCl (1 mL). After cooling to room temperature, the mixture was quenched with saturated NaHCO3 solution and was extracted with EtOAc. The extracts w... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ether.Ether.Thiourea.TMS ether protective group | Secondary alcohol | null | c1cscn1 | c1ccc2c(c1)CCCC2.c1cscn1.c1ccccc1 | HBr | Cl.CCO | null | null | CC(C)(C)[Si](C)(C)OC1CCc2cccc(NC(N)=S)c2C1.COC(OC)C(Br)c1ccccc1>Cl.CCO>OC1CCc2cccc(Nc3ncc(-c4ccccc4)s3)c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-86bfba567d944b9db0ebec0b831653d9 | CCOC(=O)CBr.OCCOc1ccc(C(=C(CCCl)c2ccccc2)c2ccccc2)cc1>>CCOC(=O)COCCOc1ccc(C(=C(CCCl)c2ccccc2)c2ccccc2)cc1 | CCOC(=O)CBr.ClCCC(=C(C1=CC=CC=C1)C1=CC=C(OCCO)C=C1)C1=CC=CC=C1.ClCCC(=C(C1=CC=CC=C1)C1=CC=C(OCCO)C=C1)C1=CC=CC=C1.[H-].[Na+]>>C(C)OC(COCCOC1=CC=C(C=C1)C(=C(CCCl)C1=CC=CC=C1)C1=CC=CC=C1)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[C:16]([CH2:17][CH2:18][Cl:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[cH:32][cH:33]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][CH2:8][CH2:9][O:10][c:11]1[cH:12][c... | CCOC(=O)CBr.OCCOc1ccc(C(=C(CCCl)c2ccccc2)c2ccccc2)cc1 | CCOC(=O)COCCOc1ccc(C(=C(CCCl)c2ccccc2)c2ccccc2)cc1 | null | null | O1CCCC1.C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4541d644834c1bca555c4310180b1edadd2271c26488a32c314314a2e4f9c76f | 1858e49e1dc71f5ec31a1f9e719a3d52cdbfbbd98e3e0f8a48e0f56789173453 | C(=C(c1ccccc1)c1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[C:7]-[C:6] | null | [] | null | null | 5 | HOUR | 2-[4-(4-Chloro-1,2-diphenyl-but-1-enyl)-phenoxy]-ethanol (Compound II) (0.3 g, 0.79 mmol) was dissolved in tetrahydrofuran (5 ml) under a nitrogen atmosphere. Sodium hydride (0.058 g, 1.21 mmol) was added in THF (5 ml) to the solution and the mixture was stirred at room temperature for an hour. Then the mixture was coo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Primary alcohol | Ester.Ether | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HBr | O1CCCC1.C1CCOC1 | null | 5 | CCOC(=O)CBr.OCCOc1ccc(C(=C(CCCl)c2ccccc2)c2ccccc2)cc1>O1CCCC1.C1CCOC1>CCOC(=O)COCCOc1ccc(C(=C(CCCl)c2ccccc2)c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c273e1961db040fcb48a169d3d35292e | CCOC(=O)COCCOc1ccc(C(=C(CCCl)c2ccccc2)c2ccccc2)cc1>>OCCOCCOc1ccc(C(=C(CCCl)c2ccccc2)c2ccccc2)cc1 | C(C)OC(COCCOC1=CC=C(C=C1)C(=C(CCCl)C1=CC=CC=C1)C1=CC=CC=C1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>ClCCC(=C(C1=CC=CC=C1)C1=CC=C(OCCOCCO)C=C1)C1=CC=CC=C1 | CCO[C:2](=[O:1])[CH2:3][O:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[C:13]([CH2:14][CH2:15][Cl:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29][cH:30]1>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([C:12](=[C:13]([CH2:14][CH2:15][C... | CCOC(=O)COCCOc1ccc(C(=C(CCCl)c2ccccc2)c2ccccc2)cc1 | OCCOCCOc1ccc(C(=C(CCCl)c2ccccc2)c2ccccc2)cc1 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C(=C(c1ccccc1)c1ccccc1)c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[#8:4]>>[#8:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 68 | [{"value": 68.0, "product": "ClCCC(=C(C1=CC=CC=C1)C1=CC=C(OCCOCCO)C=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | {2-[4-(4-Chloro-1,2-diphenyl-but-1-enyl)-phenoxy]-ethoxy}-acetic acid ethyl ester was dissolved in tetrahydrofuran at room temperature under nitrogen atmosphere. Lithium aluminium hydride was added to the solution in small portions until the reduction reaction was complete. The reaction was quenched with saturated aque... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | null | CCOC(=O)COCCOc1ccc(C(=C(CCCl)c2ccccc2)c2ccccc2)cc1>O1CCCC1>OCCOCCOc1ccc(C(=C(CCCl)c2ccccc2)c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5ebf79b70122467190ee81021dc71ef2 | CCOC(C)=O.N#Cc1cnc2[nH]ccc2c1>>O=C(O)c1cnc2[nH]ccc2c1 | C(#N)C=1C=C2C=CNC2=NC1.Cl.C(C)(=O)OCC>>N1C=CC2=CC(=CN=C12)C(=O)O | CC[O:3]C(C)=[O:1].N#[C:2][c:4]1[cH:5][n:6][c:7]2[nH:8][cH:9][cH:10][c:11]2[cH:12]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6][c:7]2[nH:8][cH:9][cH:10][c:11]2[cH:12]1 | CCOC(C)=O.N#Cc1cnc2[nH]ccc2c1 | O=C(O)c1cnc2[nH]ccc2c1 | null | null | [OH-].[K+].C(C)O | Acylation | OtherReaction | 974e60925fd89af1c3b044d933553cce925faa6db18d80fa0703702af6700b36 | 35145860eafb9e213e05cd391336310346475d6c08ca0007d2df89a15df4c11f | c1cnc2[nH]ccc2c1 | C-C-[O;H0;D2;+0:1]-C(-C)=[O;H0;D1;+0:2].N#[C;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]:[#7;a:7]:[c:6]:[c:4](-[C;H0;D3;+0:3](=[O;H0;D1;+0:2])-[OH;D1;+0:1]):[c:5] | null | [] | 90 | CELSIUS | null | null | To a solution of 5-cyano-7-azaindole XXX (50 mg, 0.35 mmol) in ethanol (10 ml), 10% aqueous potassium hydroxide (15 ml) was added. The reaction was heated at 90° C. for two days after which the reaction was allowed to cool to room temperature. The pH was adjusted to 6 with 10% HCl and diluted with ethyl acetate (100 ml... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitrile | Carboxylic acid | null | null | c1cnc2[nH]ccc2c1 | Other | [OH-].[K+].C(C)O | 90 | null | CCOC(C)=O.N#Cc1cnc2[nH]ccc2c1>[OH-].[K+].C(C)O>O=C(O)c1cnc2[nH]ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-76fe9d6c366748d9a9430ed67f67ea7f | CC(C)(C)OC(=O)n1cc(CCl)c2cc(-c3ccsc3)cnc21>>Clc1ccnc2[nH]ccc12 | C(C)(C)(C)OC(=O)N1C=C(C=2C1=NC=C(C2)C2=CSC=C2)CCl.O(C)C=1C=C(C=CC1)[Mg]Br.C(#N)[Cu].P(OC)(OC)OC>>ClC1=C2C=CNC2=NC=C1 | CC(C)(C)OC(=O)[n:7]1[c:6]2[n:5][cH:4][c:3](-c3ccsc3)[cH:2][c:10]2[c:9](C[Cl:1])[cH:8]1>>[Cl:1][c:2]1[cH:3][cH:4][n:5][c:6]2[nH:7][cH:8][cH:9][c:10]12 | CC(C)(C)OC(=O)n1cc(CCl)c2cc(-c3ccsc3)cnc21 | Clc1ccnc2[nH]ccc12 | null | null | O1CCCC1.O | Functional Group Addition | OtherReaction | b2dc3c138b8f131d418a9f7c47abfd09c18bcb3146a112ac750fa9f4cfbcf939 | b6b2ecddeec6bb391e39e621b780f9e557d353cef38c753efd210cc93abc30b7 | c1cnc2[nH]ccc2c1 | C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:1]1:[c:2]:[c;H0;D3;+0:3](-C-[Cl;H0;D1;+0:4]):[c:5]2:[cH;D2;+0:6]:[c;H0;D3;+0:7](-c3:c:c:s:c:3):[c:8]:[#7;a:9]:[c:10]:2:1>>[Cl;H0;D1;+0:4]-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[c:8]:[#7;a:9]:[c:10]2:[nH;D2;+0:1]:[c:2]:[cH;D2;+0:3]:[c:5]:2:1 | null | [] | -20 | CELSIUS | 10 | MINUTE | Into a round bottom flask was added 1.0 M of 3-methoxylphenyl magnesium bromide in Tetrahydrofuran (1.0 mL) and Tetrahydrofuran (5.0 mL, 0.062 mol) under an atmosphere of Nitrogen. The reaction mixture was cooled to −20 Celsius, followed by addition of 0.7 M of CuCN.2LiCl in Tetrahydrofuran (1 mL). After 10 minutes, Tr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Boc | Aromatic halide | c1cnc2[nH]ccc2c1.c1ccsc1 | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | Other | O1CCCC1.O | -20 | 0.166667 | CC(C)(C)OC(=O)n1cc(CCl)c2cc(-c3ccsc3)cnc21>O1CCCC1.O>Clc1ccnc2[nH]ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-85b82fd38f6d4cab867a7ba10387a77a | COc1cccc(Cc2c[nH]c3ncc(-c4ccsc4)cc23)c1>>Oc1cccc(Cc2c[nH]c3ncc(-c4ccsc4)cc23)c1 | COC=1C=C(CC2=CNC3=NC=C(C=C32)C3=CSC=C3)C=CC1.C(Cl)Cl.B(Br)(Br)Br>>S1C=C(C=C1)C=1C=C2C(=NC1)NC=C2CC=2C=C(C=CC2)O | C[O:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][c:8]2[cH:9][nH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][s:18][cH:19]4)[cH:20][c:21]23)[cH:22]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][c:8]2[cH:9][nH:10][c:11]3[n:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][s:18][cH:19]4)[cH:20][c:21]23)[cH:22]1 | COc1cccc(Cc2c[nH]c3ncc(-c4ccsc4)cc23)c1 | Oc1cccc(Cc2c[nH]c3ncc(-c4ccsc4)cc23)c1 | null | null | O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(Cc2c[nH]c3ncc(-c4ccsc4)cc23)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 26.2 | [{"value": 26.2, "product": "S1C=C(C=C1)C=1C=C2C(=NC1)NC=C2CC=2C=C(C=CC2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | Into a Round bottom flask was added compound 14 (20.0 mg, 0.0000624 mol) and Methylene chloride (4.0 mL, 0.062 mol) at room temperature. Into the reaction mixture, was added 0.1 mL BBr3 (1.0M in). The reaction mixture was allowed to room temperature for 5 hours. TLC indicated the reaction was not complete. The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1cnc2[nH]ccc2c1.c1ccsc1 | Other | O | null | 5 | COc1cccc(Cc2c[nH]c3ncc(-c4ccsc4)cc23)c1>O>Oc1cccc(Cc2c[nH]c3ncc(-c4ccsc4)cc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8b3d0f255e5142aba8a6c9ba12abde13 | Brc1cnc2[nH]ccc2c1.CC(C)[Si](Cl)(C(C)C)C(C)C>>CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(Br)cnc21 | C(C)(C)[Si](C(C)C)(C(C)C)Cl.BrC=1C=C2C=CNC2=NC1.CN(C=O)C.[H-].[Na+]>>BrC=1C=C2C(=NC1)N(C=C2)[Si](C(C)C)(C(C)C)C(C)C | [nH:11]1[cH:12][cH:13][c:14]2[cH:15][c:16]([Br:17])[cH:18][n:19][c:20]12.Cl[Si:4]([CH:2]([CH3:1])[CH3:3])([CH:5]([CH3:6])[CH3:7])[CH:8]([CH3:9])[CH3:10]>>[CH3:1][CH:2]([CH3:3])[Si:4]([CH:5]([CH3:6])[CH3:7])([CH:8]([CH3:9])[CH3:10])[n:11]1[cH:12][cH:13][c:14]2[cH:15][c:16]([Br:17])[cH:18][n:19][c:20]12 | Brc1cnc2[nH]ccc2c1.CC(C)[Si](Cl)(C(C)C)C(C)C | CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(Br)cnc21 | null | null | O | Protection | OtherReaction | 65ce4b414ae07ab2c3f60ef013cc29d623200c80057d253aa2fce78608a65270 | f0dce65f75d702dc7e016c0abdb24b26134ae5c509e2d0da4a21967fb59ed09d | c1cnc2[nH]ccc2c1 | Cl-[Si;H0;D4;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](-[C;D1;H3:9])-[C;D1;H3:10].[c:11]:[#7;a:12]:[c:13]1:[c:14]:[c:15]:[c:16]:[nH;D2;+0:17]:1>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])-[Si;H0;D4;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[n;H0;D3;+0:17]1:[c:... | 74.3 | [{"value": 74.3, "product": "BrC=1C=C2C(=NC1)N(C=C2)[Si](C(C)C)(C(C)C)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Into a Round bottom flask was added 5-bromo-7-azaindole 1 (900.0 mg, 0.004568 mol) and N,N-Dimethylformamide (25.0 mL, 0.323 mol) and Sodium hydride (0.20 g, 0.0050 mol) at room temperature. After 10 minutes, Triisopropylsilyl chloride (1.1 mL, 0.0050 mol) was added to the reaction mixture. The reaction mixture was sti... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Silyl protective group | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | HCl | O | null | 0.166667 | Brc1cnc2[nH]ccc2c1.CC(C)[Si](Cl)(C(C)C)C(C)C>O>CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(Br)cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-99b3ffdc80ae42b88153b467d0b3963e | CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(Br)cnc21.O=C(Cl)OCc1ccccc1>>CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(C(=O)OCc3ccccc3)cnc21 | ClC(=O)OCC1=CC=CC=C1.C(C)(C)(C)[Li].BrC=1C=C2C(=NC1)N(C=C2)[Si](C(C)C)(C(C)C)C(C)C.CCOCC>>C(C1=CC=CC=C1)OC(=O)C=1C=C2C(=NC1)N(C=C2)[Si](C(C)C)(C(C)C)C(C)C | Br[c:16]1[cH:15][c:14]2[cH:13][cH:12][n:11]([Si:4]([CH:2]([CH3:1])[CH3:3])([CH:5]([CH3:6])[CH3:7])[CH:8]([CH3:9])[CH3:10])[c:29]2[n:28][cH:27]1.Cl[C:17](=[O:18])[O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][CH:2]([CH3:3])[Si:4]([CH:5]([CH3:6])[CH3:7])([CH:8]([CH3:9])[CH3:10])[n:11]1[cH:12][cH:13][c... | CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(Br)cnc21.O=C(Cl)OCc1ccccc1 | CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(C(=O)OCc3ccccc3)cnc21 | null | null | O.CCCCCCC | C-C Coupling | OtherReaction | 9ceb53217bc1dc6bab78b3fd8b7a0ade286a18a872a4ed00defe4c7de80e279b | e492b0c20aeea4be57b3b35f202d8ad0bd499fdae4bec30be882f32b4e25bf9b | O=C(OCc1ccccc1)c1cnc2[nH]ccc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[#7;a:6]:[c:7]:1.Cl-[C;H0;D3;+0:8](=[O;D1;H0:9])-[#8:10]-[C:11]>>[#7;a:5]:[c:4]1:[#7;a:6]:[c:7]:[c;H0;D3;+0:1](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[#8:10]-[C:11]):[c:2]:[c:3]:1 | 50.9 | [{"value": 50.9, "product": "C(C1=CC=CC=C1)OC(=O)C=1C=C2C(=NC1)N(C=C2)[Si](C(C)C)(C(C)C)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 90 | MINUTE | Into a Round bottom flask was added compound 20 (425.0 mg, 0.001203 mol) and Ether (8.0 mL, 0.076 mol) under an atmosphere of Nitrogen, −78 Celsius. Into the reaction mixture, was added 1.7 M of tert-Butyllithium in Heptane (1.5 mL) slowly. The reaction mixture was stirred at −78 Celsius for 90 minutes, followed by add... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide | Ester | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1.c1ccccc1 | Br- | O.CCCCCCC | -78 | 1.5 | CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(Br)cnc21.O=C(Cl)OCc1ccccc1>O.CCCCCCC>CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(C(=O)OCc3ccccc3)cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6103052002624290959dfc005b6a50fd | CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(C(=O)OCc3ccccc3)cnc21>>O=C(OCc1ccccc1)c1cnc2[nH]ccc2c1 | C(C1=CC=CC=C1)OC(=O)C=1C=C2C(=NC1)N(C=C2)[Si](C(C)C)(C(C)C)C(C)C.O1CCCC1.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(C1=CC=CC=C1)OC(=O)C=1C=C2C(=NC1)NC=C2 | CC(C)[Si](C(C)C)(C(C)C)[n:15]1[c:14]2[n:13][cH:12][c:11]([C:2](=[O:1])[O:3][CH2:4][c:5]3[cH:6][cH:7][cH:8][cH:9][cH:10]3)[cH:19][c:18]2[cH:17][cH:16]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][n:13][c:14]2[nH:15][cH:16][cH:17][c:18]2[cH:19]1 | CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(C(=O)OCc3ccccc3)cnc21 | O=C(OCc1ccccc1)c1cnc2[nH]ccc2c1 | null | null | O | Deprotection | OtherReaction | 8916a76698bef40e941b3438bdfbf2019165b5bbc17fb0532f33a225359b2345 | 97c217b2f55def3964724d0808498dda438b599ce2ff7b0e4e056e4419d08380 | O=C(OCc1ccccc1)c1cnc2[nH]ccc2c1 | C-C(-C)-[Si](-C(-C)-C)(-C(-C)-C)-[n;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:1:[#7;a:6]:[c:7]>>[c:7]:[#7;a:6]:[c:5]1:[c:4]:[c:3]:[c:2]:[nH;D2;+0:1]:1 | 35.6 | [{"value": 35.6, "product": "C(C1=CC=CC=C1)OC(=O)C=1C=C2C(=NC1)NC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Into a Round bottom flask was added compound 21 (250.0 mg, 0.0006118 mol) and Tetrahydrofuran (5.0 mL, 0.062 mol) and Tetra-n-butylammonium fluoride (190 mg, 0.00073 mol). The reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water, extracted with EtOAc. The organic l... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | null | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | c1ccccc1.c1cnc2[nH]ccc2c1 | Other | O | null | 0.5 | CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(C(=O)OCc3ccccc3)cnc21>O>O=C(OCc1ccccc1)c1cnc2[nH]ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-70c23076694c4c9490af5a7c39c65a97 | O=C(OCc1ccccc1)c1cnc2[nH]ccc2c1>>O=C(O)c1cnc2[nH]ccc2c1 | C(C1=CC=CC=C1)OC(=O)C=1C=C2C(=NC1)NC=C2.CO>>N1C=CC=2C1=NC=C(C2)C(=O)O | c1ccc(C[O:3][C:2](=[O:1])[c:4]2[cH:5][n:6][c:7]3[nH:8][cH:9][cH:10][c:11]3[cH:12]2)cc1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6][c:7]2[nH:8][cH:9][cH:10][c:11]2[cH:12]1 | O=C(OCc1ccccc1)c1cnc2[nH]ccc2c1 | O=C(O)c1cnc2[nH]ccc2c1 | null | [OH-].[Pd+2].[OH-].[Pd] | null | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cnc2[nH]ccc2c1 | [#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-C-c1:c:c:c:c:c:1>>[#7;a:1]:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6] | 99 | [{"value": 99.0, "product": "N1C=CC=2C1=NC=C(C2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Into a round bottom flask was added compound 22 (55.0 mg, 0.000218 mol) and palladium hydroxide, 20 wt. % Pd on carbon, wet (20.0 mg, 0.000142 mol) and Methanol (5.0 mL, 0.12 mol) under an atmosphere of Hydrogen. The reaction mixture was stirred at room temperature overnight. Filtration and concentration gave product 1... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1cnc2[nH]ccc2c1 | Other | [OH-].[Pd+2].[OH-].[Pd] | null | 8 | O=C(OCc1ccccc1)c1cnc2[nH]ccc2c1>[OH-].[Pd+2].[OH-].[Pd]>O=C(O)c1cnc2[nH]ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d4fb084fa70a4477a98bdbf348bba5d8 | NCc1ccccc1.O=C(O)c1cnc2[nH]ccc2c1>>O=C(NCc1ccccc1)c1cnc2[nH]ccc2c1 | N1C=CC=2C1=NC=C(C2)C(=O)O.C(C1=CC=CC=C1)N.C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F.C(C)N(CC)CC.O1CCCC1.CN(C=O)C.C(Cl)Cl>>C(C1=CC=CC=C1)NC(=O)C=1C=C2C(=NC1)NC=C2 | [NH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.O[C:2](=[O:1])[c:11]1[cH:12][n:13][c:14]2[nH:15][cH:16][cH:17][c:18]2[cH:19]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][n:13][c:14]2[nH:15][cH:16][cH:17][c:18]2[cH:19]1 | NCc1ccccc1.O=C(O)c1cnc2[nH]ccc2c1 | O=C(NCc1ccccc1)c1cnc2[nH]ccc2c1 | null | null | O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCc1ccccc1)c1cnc2[nH]ccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]:[#7;a:8].[NH2;D1;+0:9]-[C:10]-[c:11]>>[#7;a:8]:[c:7]:[#7;a:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:10]-[c:11]):[c:4] | 27.6 | [{"value": 27.6, "product": "C(C1=CC=CC=C1)NC(=O)C=1C=C2C(=NC1)NC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Into a Round bottom flask was added compound 15 (35.0 mg, 0.000216 mol) and benzylamine (0.05 mL, 0.0004 mol) and PyBroP (Bromotri(pyrrolidino)phosphonium hexafluorophosphate, 200.0 mg, 0.0004318 mol) and triethylamine (0.093 mL, 0.00067 mol) and tetrahydrofuran (5.0 mL, 0.062 mol) and N,N-dimethylformamide (10.0 mL, 0... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1cnc2[nH]ccc2c1 | HO- | O | null | 8 | NCc1ccccc1.O=C(O)c1cnc2[nH]ccc2c1>O>O=C(NCc1ccccc1)c1cnc2[nH]ccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-88985bc45ea44bc699882fcb5ed3728c | COc1cccc(C(=O)c2cn(C(=O)OC(C)(C)C)c3ncc(Br)cc23)c1.OB(O)c1ccsc1>>COc1cccc(C(=O)c2cn(C(=O)OC(C)(C)C)c3ncc(-c4ccsc4)cc23)c1 | C(C)(C)(C)OC(=O)N1C=C(C=2C1=NC=C(C2)Br)C(C2=CC(=CC=C2)OC)=O.C([O-])([O-])=O.[K+].[K+].S1C=C(C=C1)B(O)O.C1CCOC1>>C(C)(C)(C)OC(=O)N1C=C(C=2C1=NC=C(C2)C2=CSC=C2)C(C2=CC(=CC=C2)OC)=O | Br[c:23]1[cH:22][n:21][c:20]2[n:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:11][c:10]([C:8]([c:7]3[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31]3)=[O:9])[c:30]2[cH:29]1.OB(O)[c:24]1[cH:25][cH:26][s:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[c:10]2[cH:11][n:12]([C:13](=[O:14])... | COc1cccc(C(=O)c2cn(C(=O)OC(C)(C)C)c3ncc(Br)cc23)c1.OB(O)c1ccsc1 | COc1cccc(C(=O)c2cn(C(=O)OC(C)(C)C)c3ncc(-c4ccsc4)cc23)c1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O | C-C Coupling | Suzuki coupling with boronic acids | 99654ab6d01fd13223243ba65f19d3eacf3e403feb79dc54a90d5c792e8a24e6 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(c1ccccc1)c1c[nH]c2ncc(-c3ccsc3)cc12 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[#7;a:5]):[c:6]:[c:7]:1.O-B(-O)-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[#16;a:11]:[c:12]:1>>[#7;a:5]:[c:4]1:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:8]2:[c:9]:[c:10]:[#16;a:11]:[c:12]:2):[c:7]:[c:6]:1 | null | [] | 70 | CELSIUS | 8 | HOUR | Azaindole 26 (33 mg, 0.00076 mol), Potassium carbonate (44 mg, 0.00032 mol), 3-thiophene boronic acid (20 mg, 0.0002 mol), THF (7 mL), water (1.5 mL), and tetrakis(triphenylphosphine)palladium (0) (5 mg, 0.000004 mol) were added to a round bottom flask. The reaction mixture was stirred under nitrogen at 70° C. for over... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cnc2[nH]ccc2c1.c1ccsc1 | c1cnc2[nH]ccc2c1.c1ccsc1 | c1ccccc1.c1cnc2[nH]ccc2c1.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 | 70 | 8 | COc1cccc(C(=O)c2cn(C(=O)OC(C)(C)C)c3ncc(Br)cc23)c1.OB(O)c1ccsc1>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>COc1cccc(C(=O)c2cn(C(=O)OC(C)(C)C)c3ncc(-c4ccsc4)cc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8988b9ac601a49c4bc8d816c13dd86ed | Brc1cnc2[nH]ccc2c1.COc1cc(CBr)cc(OC)c1>>COc1cc(Cc2cc3cccnc3[nH]2)cc(OC)c1 | COC=1C=C(CBr)C=C(C1)OC.C[Mg]Br.BrC=1C=C2C=CNC2=NC1.C(Cl)Cl>>COC=1C=C(CC2=CC=3C(=NC=CC3)N2)C=C(C1)OC | Br[c:11]1[cH:10][c:9]2[cH:8][cH:7][nH:15][c:14]2[n:13][cH:12]1.Br[CH2:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[cH:20][c:17]([O:18][CH3:19])[cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][c:7]2[cH:8][c:9]3[cH:10][cH:11][cH:12][n:13][c:14]3[nH:15]2)[cH:16][c:17]([O:18][CH3:19])[cH:20]1 | Brc1cnc2[nH]ccc2c1.COc1cc(CBr)cc(OC)c1 | COc1cc(Cc2cc3cccnc3[nH]2)cc(OC)c1 | null | [Cl-].[Cl-].[Zn+2] | null | C-C Coupling | OtherReaction | c1152109619ed328d90aa3d88cfa5ab2a3e8fc844d9a27aa9416ab758e66804c | 84e12b0159f1d183204538a38a0b22f090552039c6c4b4ca4a95700e436c4e5e | c1ccc(Cc2cc3cccnc3[nH]2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].Br-[c;H0;D3;+0:5]1:[c:6]:[c:7]2:[c:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:[c:13]:1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[c;H0;D3;+0:9]1:[#7;a:10]:[c:11]2:[#7;a:12]:[c:13]:[cH;D2;+0:5]:[c:6]:[c:7]:2:[c:8]:1):[c:4] | 4.4 | [{"value": 4.4, "product": "COC=1C=C(CC2=CC=3C(=NC=CC3)N2)C=C(C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a round bottom flask, under an atmosphere of nitrogen, methylmagnesium bromide (0.16 mL, 1.4 mmol) was added to a solution of 7-azaindole (1) (0.150 g, 1.27 mmol) in anhydrous methylene chloride (12 mL, 0.19 mol), at room temperature. The resulting mixture was stirred at room temperature for one hour before zinc d... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide | null | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | c1ccccc1.c1cnc2[nH]ccc2c1 | Br- | [Cl-].[Cl-].[Zn+2] | null | null | Brc1cnc2[nH]ccc2c1.COc1cc(CBr)cc(OC)c1>[Cl-].[Cl-].[Zn+2]>COc1cc(Cc2cc3cccnc3[nH]2)cc(OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-395b2e6f341c4c33875dea5e7301a11f | O=C(Cl)c1ccccc1.c1cnc2[nH]ccc2c1>>O=C(c1ccccc1)c1c[nH]c2ncccc12 | COC=1C=C(C(=O)Cl)C=CC1.C(C1=CC=CC=C1)(=O)Cl.N1C=CC2=CC=CN=C12>>C(C1=CC=CC=C1)(=O)C1=CNC2=NC=CC=C12 | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1.[cH:9]1[cH:10][nH:11][c:12]2[n:13][cH:14][cH:15][cH:16][c:17]12>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][nH:11][c:12]2[n:13][cH:14][cH:15][cH:16][c:17]12 | O=C(Cl)c1ccccc1.c1cnc2[nH]ccc2c1 | O=C(c1ccccc1)c1c[nH]c2ncccc12 | null | null | null | C-C Coupling | Friedel-Crafts acylation | 1bac1dd3ebf1eec66abc5940fc68d0b3d89999c986d197b8a60e9b2fcd4b0fbd | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(c1ccccc1)c1c[nH]c2ncccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[c:6]:[#7;a:7]:[c:8]1:[#7;a:9]:[c:10]:[cH;D2;+0:11]:[c:12]:1:[c:13]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3](:[c:4]):[c:5])-[c;H0;D3;+0:11]1:[c:10]:[#7;a:9]:[c:8](:[#7;a:7]:[c:6]):[c:12]:1:[c:13] | null | [] | null | null | null | null | Compound 41 was prepared from 7-azaindole 2 using aluminum chloride as described previously for the synthesis of Compound 25, with benzoyl chloride substituted for m-methoxy-benzoyl chloride.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | c1ccccc1.c1cnc2[nH]ccc2c1 | HCl | null | null | null | O=C(Cl)c1ccccc1.c1cnc2[nH]ccc2c1>>O=C(c1ccccc1)c1c[nH]c2ncccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f90e7fc10824646b0d69448bb568be6 | COc1cccc(C(=O)c2cn([Si](C(C)C)(C(C)C)C(C)C)c3ncc(Br)cc23)c1.Nc1ccccc1>>COc1cccc(C(=O)c2c[nH]c3ncc(Nc4ccccc4)cc23)c1 | NC1=CC=CC=C1.CC(C)([O-])C.[Na+].COC=1C=C(C=CC1)C(=O)C1=CN(C2=NC=C(C=C21)Br)[Si](C(C)C)(C(C)C)C(C)C.C(C)(C)(C)P(C(C)(C)C)C(C)(C)C>>COC=1C=C(C=CC1)C(=O)C1=CNC2=NC=C(C=C21)NC2=CC=CC=C2 | CC(C)[Si](C(C)C)(C(C)C)[n:12]1[cH:11][c:10]([C:8]([c:7]2[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:26]2)=[O:9])[c:25]2[c:13]1[n:14][cH:15][c:16](Br)[cH:24]2.[NH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[c:10]2[cH:11][nH:12][c:13]3[n:14][cH:15][c:16]([NH:17][c... | COc1cccc(C(=O)c2cn([Si](C(C)C)(C(C)C)C(C)C)c3ncc(Br)cc23)c1.Nc1ccccc1 | COc1cccc(C(=O)c2c[nH]c3ncc(Nc4ccccc4)cc23)c1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 1e3cb8926352971c9972a67dd9bd9b914a4cf24cd9a13edbc2647774fe6ea3bf | 7dcec635abbef9e7d7353b185ca71653bb7e43a4c6979f411a400645c4386a53 | O=C(c1ccccc1)c1c[nH]c2ncc(Nc3ccccc3)cc12 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]2:[c:5](:[c:6]:1):[c:7](-[C:8]=[O;D1;H0:9]):[c:10]:[n;H0;D3;+0:11]:2-[Si](-C(-C)-C)(-C(-C)-C)-C(-C)-C.[NH2;D1;+0:12]-[c:13](:[c:14]):[c:15]>>[O;D1;H0:9]=[C:8]-[c:7]1:[c:10]:[nH;D2;+0:11]:[c:4]2:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]):[c:6]:[c:5]:1:2 | 28 | [{"value": 28.0, "product": "COC=1C=C(C=CC1)C(=O)C1=CNC2=NC=C(C=C21)NC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | Compound 292 (135 mg, 0.2769 mmol) was dissolved in toluene (4.2 mL), under and atmosphere of argon. Aniline (0.154 mL, 1.69 mmol) and sodium tert-butoxide (57.7 mg, 0.60 mmol) were added to the reaction. Into the reaction was added tri-tert-butyl-phosphine (9.0 mg, 0.040 mmol) and Tris(dibenzylideneacetone)dipalladium... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Silyl protective group | Secondary amine | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | c1ccccc1.c1cnc2[nH]ccc2c1.c1ccccc1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C | 95 | null | COc1cccc(C(=O)c2cn([Si](C(C)C)(C(C)C)C(C)C)c3ncc(Br)cc23)c1.Nc1ccccc1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C>COc1cccc(C(=O)c2c[nH]c3ncc(Nc4ccccc4)cc23)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4fd4253ff2664922b766e3523de10f2e | COc1cccc(C(=O)c2c[nH]c3ncc(Nc4ccccc4)cc23)c1>>O=C(c1cccc(O)c1)c1c[nH]c2ncc(Nc3ccccc3)cc12 | COC=1C=C(C=CC1)C(=O)C1=CNC2=NC=C(C=C21)NC2=CC=CC=C2.B(Br)(Br)Br>>OC=1C=C(C=CC1)C(=O)C1=CNC2=NC=C(C=C21)NC2=CC=CC=C2 | C[O:8][c:7]1[cH:6][cH:5][cH:4][c:3]([C:2](=[O:1])[c:10]2[cH:11][nH:12][c:13]3[n:14][cH:15][c:16]([NH:17][c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[cH:24][c:25]23)[cH:9]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][c:7]([OH:8])[cH:9]1)[c:10]1[cH:11][nH:12][c:13]2[n:14][cH:15][c:16]([NH:17][c:18]3[cH:19][cH:20][cH:21][cH:22]... | COc1cccc(C(=O)c2c[nH]c3ncc(Nc4ccccc4)cc23)c1 | O=C(c1cccc(O)c1)c1c[nH]c2ncc(Nc3ccccc3)cc12 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccccc1)c1c[nH]c2ncc(Nc3ccccc3)cc12 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | Compound 293 (26.6 mg, 0.079 mmol) was dissolved in methylene chloride (10 mL) under an atmosphere of nitrogen. Into the reaction mixture was added 1.0 M boron tribromide in methylene chloride (0.3 mL). The reaction was stirred at room temperature overnight. The solvent evaporated over time, so methylene chloride (10 m... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1cnc2[nH]ccc2c1.c1ccccc1 | Other | C(Cl)Cl | null | 8 | COc1cccc(C(=O)c2c[nH]c3ncc(Nc4ccccc4)cc23)c1>C(Cl)Cl>O=C(c1cccc(O)c1)c1c[nH]c2ncc(Nc3ccccc3)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-21086f2d03d74c19b2f186ae1e9e9f29 | O=C(O)c1cc(F)cc([N+](=O)[O-])c1.[Cl-]>>O=C(Cl)c1cc(F)cc([N+](=O)[O-])c1 | FC=1C=C(C(=O)O)C=C(C1)[N+](=O)[O-].N1C=CC2=CC=CN=C12.[Cl-].[Cl-].[Cl-].[Al+3]>>FC=1C=C(C(=O)Cl)C=C(C1)[N+](=O)[O-] | O[C:2](=[O:1])[c:4]1[cH:5][c:6]([F:7])[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1.[Cl-:3]>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][c:6]([F:7])[cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13]1 | O=C(O)c1cc(F)cc([N+](=O)[O-])c1.[Cl-] | O=C(Cl)c1cc(F)cc([N+](=O)[O-])c1 | null | null | S(=O)(Cl)Cl.C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_Salt | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[Cl-;H0;D0:6]>>[Cl;H0;D1;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 1 | HOUR | 3-fluoro-5-nitrobenzoic acid (2.00 g, 10.8 mmol) was dissolved in thionyl chloride (20.0 mL) and the reaction was heated to reflux overnight. The reaction was cooled and was concentrated to provide a white solid which was dried under vacuum overnight. Compound 2 (512 mg, 4.33 mmol) was dissolved in methylene chloride (... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HO- | S(=O)(Cl)Cl.C(Cl)Cl | null | 1 | O=C(O)c1cc(F)cc([N+](=O)[O-])c1.[Cl-]>S(=O)(Cl)Cl.C(Cl)Cl>O=C(Cl)c1cc(F)cc([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7199abe6a749449a9caa0f498e281032 | O=C(c1cc([N+](=O)[O-])ccc1F)c1c[nH]c2ncccc12>>Nc1ccc(F)c(-c2[nH]c3ncccc3c2C=O)c1 | FC1=C(C=C(C=C1)[N+](=O)[O-])C(=O)C1=CNC2=NC=CC=C21.C(C)O.O1CCCC1>>FC1=C(C=C(C=C1)N)C1=C(C=2C(=NC=CC2)N1)C=O | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([F:6])[c:7]([C:17]([c:16]2[cH:8][nH:9][c:10]3[n:11][cH:12][cH:13][cH:14][c:15]32)=[O:18])[cH:19]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([F:6])[c:7](-[c:8]2[nH:9][c:10]3[n:11][cH:12][cH:13][cH:14][c:15]3[c:16]2[CH:17]=[O:18])[cH:19]1 | O=C(c1cc([N+](=O)[O-])ccc1F)c1c[nH]c2ncccc12 | Nc1ccc(F)c(-c2[nH]c3ncccc3c2C=O)c1 | null | [Fe] | Cl | Functional Group Interconversion | OtherReaction | 8316c16cd2dd198a44007c9a2f5ac799636060e30b4f4c60b3052f9604ac2e2b | 1a01301d7fc4cd1d394b18e2088585f62bba220e7c2ff1786b6724e18199667f | c1ccc(-c2cc3cccnc3[nH]2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[c;H0;D3;+0:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7]2:[c:8]:[c:9](:[#7;a:10]):[#7;a:11]:[cH;D2;+0:12]:2):[c:13](-[F;D1;H0:14]):[c:15]:[c:16]:1>>[#7;a:10]:[c:9]1:[#7;a:11]:[c;H0;D3;+0:12](-[c;H0;D3;+0:4]2:[c:3]:[c:2](-[NH2;D1;+0:1]):[c:16]:[c:15]:[c:13]:2-[F;D1;H0:14]):[c:7](-[CH;D2;+0:5... | null | [] | null | null | null | null | Compound 295 (130 mg, 0.46 mmol) was suspended in 6 M hydrochloric acid (10.0 mL) and ethanol (5.0 mL) unser an atmosphere of nitrogen. Tetrahydrofuran (5.0 mL) was added to completely dissolve the compound. Iron (229 mg) was added to the mixture and the reaction was heated to reflux for 2.5 hours. The reaction was coo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitro group | Aldehyde.Primary amine | c1ccccc1.c1cnc2[nH]ccc2c1 | c1ccccc1.c1cnc2[nH]ccc2c1 | c1ccccc1.c1cnc2[nH]ccc2c1 | Other | [Fe].Cl | null | null | O=C(c1cc([N+](=O)[O-])ccc1F)c1c[nH]c2ncccc12>[Fe].Cl>Nc1ccc(F)c(-c2[nH]c3ncccc3c2C=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dd1152c3a76049c6ad7c10be67ed960f | Brc1ccc2c3c(cccc13)CC2.CC(C)OB(OC(C)C)OC(C)C>>OB(O)c1ccc2c3c(cccc13)CC2 | CCCCCC.C(CCC)[Li].C(C)(C)OB(OC(C)C)OC(C)C.BrC1=CC=C2CCC=3C=CC=C1C32.Cl>>C1CC2=CC=C(C3=CC=CC1=C23)B(O)O | Br[c:4]1[cH:5][cH:6][c:7]2[c:8]3[c:9]([cH:10][cH:11][cH:12][c:13]13)[CH2:14][CH2:15]2.CC(C)O[B:2]([O:1]C(C)C)[O:3]C(C)C>>[OH:1][B:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]3[c:9]([cH:10][cH:11][cH:12][c:13]13)[CH2:14][CH2:15]2 | Brc1ccc2c3c(cccc13)CC2.CC(C)OB(OC(C)C)OC(C)C | OB(O)c1ccc2c3c(cccc13)CC2 | null | null | CCOCC.C1(=CC=CC=C1)C | Miscellaneous | Preparation of boronic acids | 20702535d1548a560c369649c0cf6ee97c055bd1c92b6d7333e31b3e6d34e027 | dafd25fbe01879c365f8c874026e570f49824f4bb82016b29d0c5d21aeb58ca3 | c1cc2c3c(cccc3c1)CC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[c:6].C-C(-C)-O-[B;H0;D3;+0:7](-[O;H0;D2;+0:8]-C(-C)-C)-[O;H0;D2;+0:9]-C(-C)-C>>[OH;D1;+0:8]-[B;H0;D3;+0:7](-[OH;D1;+0:9])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[c:6] | 45 | [{"value": 45.0, "product": "C1CC2=CC=C(C3=CC=CC1=C23)B(O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Commercially available 5-bromo acenaphthene in an amount of 11.7 g was dissolved into a mixed solution of dehydrated toluene in an amount 50 milliliter and dehydrated ether in an amount of 50 milliliter, and the resultant solution was cooled down to −40° C. under an atmosphere of argon gas. Thirty five milliliter of 1.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Boronic acid | c1cc2c3c(cccc3c1)CC2 | c1cc2c3c(cccc3c1)CC2 | c1cc2c3c(cccc3c1)CC2 | HBr | CCOCC.C1(=CC=CC=C1)C | null | null | Brc1ccc2c3c(cccc13)CC2.CC(C)OB(OC(C)C)OC(C)C>CCOCC.C1(=CC=CC=C1)C>OB(O)c1ccc2c3c(cccc13)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1164ab4d036488f946a39cdbfdcd8e0 | Brc1ccc(I)cc1.OB(O)c1ccc2c3c(cccc13)CC2>>Brc1ccc(-c2ccc3c4c(cccc24)CC3)cc1 | C([O-])([O-])=O.[Na+].[Na+].C1CC2=CC=C(C3=CC=CC1=C23)B(O)O.BrC1=CC=C(C=C1)I>>BrC1=CC=C(C=C1)C1=CC=C2CCC=3C=CC=C1C32 | I[c:5]1[cH:4][cH:3][c:2]([Br:1])[cH:19][cH:18]1.OB(O)[c:6]1[cH:7][cH:8][c:9]2[c:10]3[c:11]([cH:12][cH:13][cH:14][c:15]13)[CH2:16][CH2:17]2>>[Br:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]3[c:10]4[c:11]([cH:12][cH:13][cH:14][c:15]24)[CH2:16][CH2:17]3)[cH:18][cH:19]1 | Brc1ccc(I)cc1.OB(O)c1ccc2c3c(cccc13)CC2 | Brc1ccc(-c2ccc3c4c(cccc24)CC3)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | bbc412517dcb6c0b56dab3cbae1bbd9490fb399bfcffd5cc8e7523c757c37d7b | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3c4c(cccc24)CC3)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](:[c:10]):[c:11]>>[c:10]:[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:7]:[c:8] | 100 | [{"value": 100.0, "product": "BrC1=CC=C(C=C1)C1=CC=C2CCC=3C=CC=C1C32", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.5, "product": "BrC1=CC=C(C=C1)C1=CC=C2CCC=3C=CC=C1C32", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Five point nine gram of the 5-acenaphthene boronic acid obtained and 10.2 gram of 4-bromo iodobenzene were dissolved into 100 milliliter of toluene. Further adding tetrakistriphenylphosphinepalladium in an amount of 1.7 g and 2M-sodium carbonate aqueous solution in an amount of 45 milliliter, an atmospheric air was rep... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1cc2c3c(cccc3c1)CC2 | c1ccccc1.c1cc2c3c(cccc3c1)CC2 | c1ccccc1.c1cc2c3c(cccc3c1)CC2 | 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.C1(=CC=CC=C1)C | null | null | Brc1ccc(I)cc1.OB(O)c1ccc2c3c(cccc13)CC2>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.C1(=CC=CC=C1)C>Brc1ccc(-c2ccc3c4c(cccc24)CC3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0174edb295e24aa8bb39b70d6165f0c0 | C[N+](=O)[O-].Cc1ccc(C=O)cc1C>>Cc1ccc(/C=C/[N+](=O)[O-])cc1C | CC=1C=C(C=O)C=CC1C.C(C)(=O)[O-].[NH4+].[N+](=O)([O-])C.C(C)(=O)OC(C)=O>>CC=1C=C(C=CC1C)\C=C\[N+](=O)[O-] | [CH3:7][N+:8](=[O:9])[O-:10].O=[CH:6][c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:12]([CH3:13])[cH:11]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](/[CH:6]=[CH:7]/[N+:8](=[O:9])[O-:10])[cH:11][c:12]1[CH3:13] | C[N+](=O)[O-].Cc1ccc(C=O)cc1C | Cc1ccc(/C=C/[N+](=O)[O-])cc1C | null | null | C(C)(=O)O | C-C Coupling | OtherReaction | 7ede86d40d3d69f429dde089476c8b7ffa9b74bf3050590255e6323d013c2daf | f736727903c0ad5511d468246b8e380897fd19905174c118ffa4ed4d3651f6ea | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[#7;+:6](-[O;-;D1;H0:7])=[O;D1;H0:8]>>[O;-;D1;H0:7]-[#7;+:6](=[O;D1;H0:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 66.2 | [{"value": 66.0, "product": "CC=1C=C(C=CC1C)\\C=C\\[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.2, "product": "CC=1C=C(C=CC1C)\\C=C\\[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3,4-dimethylbenzaldehyde (20 mL, 0.15 mol), ammonium acetate (12.5 g, 0.16 mol), glacial acetic acid (65 mL), nitromethane (34 mL, 0.63 mol), and acetic anhydride (3.0 mL, 0.032 mol) is refluxed for 2 hours. The reaction is concentrated to an oil, then dichloromethane (100 mL) is added, and the solution i... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Enamine | null | null | c1ccccc1 | HO- | C(C)(=O)O | null | null | C[N+](=O)[O-].Cc1ccc(C=O)cc1C>C(C)(=O)O>Cc1ccc(/C=C/[N+](=O)[O-])cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cfc1e953b76e4abc85d8c0c35448e1c9 | COc1ccc(CCNC(CN)c2ccc(C)c(C)c2)cc1.O=C(n1ccnc1)n1ccnc1>>COc1ccc(CCN2C(=O)NCC2c2ccc(C)c(C)c2)cc1 | COC1=CC=C(C=C1)CCNC(CN)C1=CC(=C(C=C1)C)C.C(=O)(N1C=NC=C1)N1C=NC=C1>>COC1=CC=C(C=C1)CCN1C(NCC1C1=CC(=C(C=C1)C)C)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][CH:14]([CH2:13][NH2:12])[c:15]2[cH:16][cH:17][c:18]([CH3:19])[c:20]([CH3:21])[cH:22]2)[cH:23][cH:24]1.c1cn([C:10](n2ccnc2)=[O:11])cn1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[C:10](=[O:11])[NH:12][CH2:13][CH:14]2[c:15]2[cH:16][cH:17][c:18]([CH3:1... | COc1ccc(CCNC(CN)c2ccc(C)c(C)c2)cc1.O=C(n1ccnc1)n1ccnc1 | COc1ccc(CCN2C(=O)NCC2c2ccc(C)c(C)c2)cc1 | null | null | CN(C)C=O.C(C)(=O)OCC | Acylation | OtherReaction | d50ab08ba9b21e12798143263731d8e47a5fd3f51bea1aefeed0abbfa63d5047 | 092fb1988ce3c31a0210cc9ec123f317c79841c29a05a3f2098134944f12c379 | O=C1NCC(c2ccccc2)N1CCc1ccccc1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4](-[c:5])-[C:6]-[NH2;D1;+0:7].[O;D1;H0:8]=[C;H0;D3;+0:9](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C:4](-[c:5])-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:9]-1=[O;D1;H0:8] | 65 | [{"value": 65.0, "product": "COC1=CC=C(C=C1)CCN1C(NCC1C1=CC(=C(C=C1)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.9, "product": "COC1=CC=C(C=C1)CCN1C(NCC1C1=CC(=C(C=C1)C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 30 | MINUTE | To a solution of N1-[2-(4-methoxyphenyl)ethyl]-1-(3,4-dimethylphenyl)-1,2-ethanediamine (10.6 g, 0.0356 mol) in dry DMF (55 mL) is added 1,1′-carbonyldiimidazole (6.4 g, 0.0395 mol). The reaction is stirred at 50° C. for 30 minutes, cooled, diluted with ethyl acetate (300 mL), and washed with 0.5 N HCl and brine. The o... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | C1C[NH]CN1 | c1ccccc1.C1C[NH]CN1.c1ccccc1 | Other | CN(C)C=O.C(C)(=O)OCC | 50 | 0.5 | COc1ccc(CCNC(CN)c2ccc(C)c(C)c2)cc1.O=C(n1ccnc1)n1ccnc1>CN(C)C=O.C(C)(=O)OCC>COc1ccc(CCN2C(=O)NCC2c2ccc(C)c(C)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-61fc876da5f54b26bfc68d8caf3a79c8 | COc1ccc(CCN2C(=O)NCC2c2ccc(C)c(C)c2)cc1.ClCCl>>COc1ccc(CCN2C(=O)N(N)CC2c2ccc(C)c(C)c2)cc1.Cl | [OH-].[NH4+].COC1=CC=C(C=C1)CCN1C(NCC1C1=CC(=C(C=C1)C)C)=O.N(=O)[O-].[Na+].ClCCl>>Cl.NN1C(N(C(C1)C1=CC(=C(C=C1)C)C)CCC1=CC=C(C=C1)OC)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[C:10](=[O:11])[NH:12][CH2:14][CH:15]2[c:16]2[cH:17][cH:18][c:19]([CH3:20])[c:21]([CH3:22])[cH:23]2)[cH:24][cH:25]1.ClC[Cl:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[C:10](=[O:11])[N:12]([NH2:13])[CH2:14][CH:15]2[c:16]2[cH:17][cH:18][c:19]([CH3:... | COc1ccc(CCN2C(=O)NCC2c2ccc(C)c(C)c2)cc1.ClCCl | COc1ccc(CCN2C(=O)N(N)CC2c2ccc(C)c(C)c2)cc1.Cl | null | [Zn] | O.C(C)(=O)O | Miscellaneous | OtherReaction | 844ead4ea7cb048dfffc540c9f0257c074b54a8b0c0a2faaddac1a0f754bbb07 | b4208230c4f42580304215eb3ce59f3b440922e296f7400dfc07925a99e171b1 | O=C1NCC(c2ccccc2)N1CCc1ccccc1 | Cl-C-[Cl;H0;D1;+0:1].[C:2]-[#7:3]1-[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-1=[O;D1;H0:8]>>[C:2]-[#7:3]1-[C:4]-[C:5]-[N;H0;D3;+0:6](-[N;D1;H2:9])-[C:7]-1=[O;D1;H0:8].[ClH;D0;+0:1] | 81 | [{"value": 81.0, "product": "Cl.NN1C(N(C(C1)C1=CC(=C(C=C1)C)C)CCC1=CC=C(C=C1)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 8 | CELSIUS | 30 | MINUTE | To a solution of 1-[2-(4-methoxyphenyl)ethyl]-5-(3,4-dimethylphenyl)-2-imidazolidinone (2.0 g, 0.0062 mol) in glacial acetic acid (21 mL) is added a solution of sodium nitrite (0.58 g, 0.0084 mol) in H2O (2.8 mL) at room temperature over 2 minutes. The solution is stirred for 30 minutes and then cooled to 8° C. Zinc du... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Urea | Acylhydrazine.Urea | C1C[NH]CN1 | C1C[NH]C[NH]1 | c1ccccc1.C1C[NH]C[NH]1.c1ccccc1 | Other | [Zn].O.C(C)(=O)O | 8 | 0.5 | COc1ccc(CCN2C(=O)NCC2c2ccc(C)c(C)c2)cc1.ClCCl>[Zn].O.C(C)(=O)O>COc1ccc(CCN2C(=O)N(N)CC2c2ccc(C)c(C)c2)cc1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6e0c65a18d89421a8b5bbe7682cd0650 | COc1ccc(CCN)cc1>>COc1ccc(CCNC(C#N)c2ccc(OC)cc2)cc1 | COC1=CC=C(CCN)C=C1>>COC1=CC=C(C=C1)C(C#N)NCCC1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH2:9])[cH:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][CH:10]([C:11]#[N:12])[c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][cH:20]2)[cH:21][cH:22]1 | COc1ccc(CCN)cc1 | COc1ccc(CCNC(C#N)c2ccc(OC)cc2)cc1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | ab9098f36fb99d940166adcbf6ade8b799cb986f7f9be48dc6325eb784b7207f | 0d6b0457cf4162bb711561b092151571adf9dfb8ffd0397d0e0ebf83f79d5aee | c1ccc(CCNCc2ccccc2)cc1 | [C:1]-[C:2]-[NH2;D1;+0:3]>>[C:4]-[C:5](-[c:6])-[NH;D2;+0:3]-[C:2]-[C:1] | null | [] | 125 | CELSIUS | null | null | 4-Methoxyphenethylamine (1.2 mL, 8.2 mmol) and methanol (0.5 mL) are added to the crude material obtained above. The solution is heated to 125° C. for 15 minutes in a microwave reaction vessel after which the solution is concentrated in vacuo and the crude product obtained is used without further purification.
Conditio... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Ether.Nitrile.Secondary amine | null | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | CO | 125 | null | COc1ccc(CCN)cc1>CO>COc1ccc(CCNC(C#N)c2ccc(OC)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9e49041f207c48428e64c3482fdb574c | COc1ccc(CCNC(C#N)c2ccc(OC)cc2)cc1>>COc1ccc(CCNC(CN)c2ccc(OC)cc2)cc1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].COC1=CC=C(C=C1)C(C#N)NCCC1=CC=C(C=C1)OC>>COC1=CC=C(C=C1)CCNC(CN)C1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][CH:10]([C:11]#[N:12])[c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][cH:20]2)[cH:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][CH:10]([CH2:11][NH2:12])[c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][cH:20]2)[cH:21][cH:22]1 | COc1ccc(CCNC(C#N)c2ccc(OC)cc2)cc1 | COc1ccc(CCNC(CN)c2ccc(OC)cc2)cc1 | null | null | C(C)OCC | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(CCNCc2ccccc2)cc1 | [#7:1]-[C:2](-[c:3])-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[#7:1]-[C:2](-[c:3])-[CH2;D2;+0:4]-[NH2;D1;+0:5] | null | [] | 5 | CELSIUS | 1 | HOUR | The crude (4-methoxyphenyl)-[2-(4-methoxyphenyl)ethylamino]-acetonitrile obtained in the above procedure is dissolved in diethyl ether (20 mL) and this solution is slowly added to an ice-cold solution of lithium aluminum hydride (1.0M, 16 mL, 16 mmol) in diethyl ether. The cooling bath is removed and the solution is al... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.c1ccccc1 | null | C(C)OCC | 5 | 1 | COc1ccc(CCNC(C#N)c2ccc(OC)cc2)cc1>C(C)OCC>COc1ccc(CCNC(CN)c2ccc(OC)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d80edfccb92b467dbf498aed13f2b143 | COc1ccc(CCN2C(=O)N(N)CC2c2ccc(C)c(C)c2)cc1.CS(=O)(=O)Cl>>COc1ccc(CCN2C(=O)N(NS(C)(=O)=O)CC2c2ccc(C)c(C)c2)cc1 | CS(=O)(=O)Cl.Cl.NN1C(N(C(C1)C1=CC(=C(C=C1)C)C)CCC1=CC=C(C=C1)OC)=O.CCN(C(C)C)C(C)C>>CS(=O)(=O)NN1C(N(C(C1)C1=CC(=C(C=C1)C)C)CCC1=CC=C(C=C1)OC)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[C:10](=[O:11])[N:12]([NH2:13])[CH2:18][CH:19]2[c:20]2[cH:21][cH:22][c:23]([CH3:24])[c:25]([CH3:26])[cH:27]2)[cH:28][cH:29]1.Cl[S:14]([CH3:15])(=[O:16])=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[C:10](=[O:11])[N:12]([NH:13][S:14]([CH3:15])(=... | COc1ccc(CCN2C(=O)N(N)CC2c2ccc(C)c(C)c2)cc1.CS(=O)(=O)Cl | COc1ccc(CCN2C(=O)N(NS(C)(=O)=O)CC2c2ccc(C)c(C)c2)cc1 | null | null | ClCCl | Acylation | OtherReaction | 1d7782d13faad590a954d6d254ec5fc1e568084640ff236ac5cf433eecd9384e | 53d94e045a6cc897b7aa22bd88fc0cbf2a5e03cfb9e60b6d258d000dc8961a94 | O=C1NCC(c2ccccc2)N1CCc1ccccc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[#7:6]1-[C:7]-[C:8]-[#7:9](-[NH2;D1;+0:10])-[C:11]-1=[O;D1;H0:12]>>[C:5]-[#7:6]1-[C:7]-[C:8]-[#7:9](-[NH;D2;+0:10]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:11]-1=[O;D1;H0:12] | 48.2 | [{"value": 48.0, "product": "CS(=O)(=O)NN1C(N(C(C1)C1=CC(=C(C=C1)C)C)CCC1=CC=C(C=C1)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.2, "product": "CS(=O)(=O)NN1C(N(C(C1)C1=CC(=C(C=C1)C)C)CCC1=CC=C(C=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | A solution of 1-amino-3-[2-(4-methoxyphenyl)-ethyl]-4-(3,4-dimethylphenyl)-2-imidazolidinone hydrochloride (300 mg, 0.80 mmol) in dichloromethane (3.0 mL) and Hunig's base (0.31 mL, 1.8 mmol) is cooled in an ice bath and methanesulfonyl chloride (0.068 mL, 0.88 mmol) is added dropwise. The reaction is stirred cold for ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1C[NH]C[NH]1.c1ccccc1 | HCl | ClCCl | null | 0.75 | COc1ccc(CCN2C(=O)N(N)CC2c2ccc(C)c(C)c2)cc1.CS(=O)(=O)Cl>ClCCl>COc1ccc(CCN2C(=O)N(NS(C)(=O)=O)CC2c2ccc(C)c(C)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e35e3c5e220b4586b435a236b43a5731 | COc1ccc(CCCN2C(=O)NCC2c2ccc(OC)cc2)cc1>>COc1ccc(CCCN2C(=O)N(N)CC2c2ccc(OC)cc2)cc1 | COC1=CC=C(C=C1)CCCN1C(NCC1C1=CC=C(C=C1)OC)=O.N(=O)[O-].[Na+]>>NN1C(N(C(C1)C1=CC=C(C=C1)OC)CCCC1=CC=C(C=C1)OC)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][N:10]2[C:11](=[O:12])[NH:13][CH2:15][CH:16]2[c:17]2[cH:18][cH:19][c:20]([O:21][CH3:22])[cH:23][cH:24]2)[cH:25][cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][N:10]2[C:11](=[O:12])[N:13]([NH2:14])[CH2:15][CH:16]2[c:17]2[cH:18][cH:19][c:20]([O:... | COc1ccc(CCCN2C(=O)NCC2c2ccc(OC)cc2)cc1 | COc1ccc(CCCN2C(=O)N(N)CC2c2ccc(OC)cc2)cc1 | null | [Zn] | O.C(C)(=O)O | Miscellaneous | OtherReaction | ccd4775c8dee9e6e01b1e3aeda4923bd0a200db34cc134d9940048e3fe429d72 | 44dc6f378d07fd5433bf00a26d0988985866ee1c977ade741a011139c56e5666 | O=C1NCC(c2ccccc2)N1CCCc1ccccc1 | [C:1]-[#7:2]1-[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-1=[O;D1;H0:7]>>[C:1]-[#7:2]1-[C:3]-[C:4]-[N;H0;D3;+0:5](-[N;D1;H2:8])-[C:6]-1=[O;D1;H0:7] | 109.3 | [{"value": 109.3, "product": "NN1C(N(C(C1)C1=CC=C(C=C1)OC)CCCC1=CC=C(C=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 5 | MINUTE | To a solution of 1-[3-(4-methoxyphenyl)propyl]-5-[(4-methoxy)-phenyl]-2-imidazolidinone (0.6 g, 1.75 mmol) in acetic acid (15 mL) is added dropwise a solution of NaNO2 (0.12 g, 1.8 mmol) in water (1 mL). The mixture is cooled in an ice bath to 5° C. and zinc dust (0.6 g, 9 mmol) is added in portions (starting with 0.5 ... | 10.6084/m9.figshare.5104873.v1 | null | Urea | Acylhydrazine | C1C[NH]CN1 | C1C[NH]C[NH]1 | c1ccccc1.C1C[NH]C[NH]1.c1ccccc1 | Other | [Zn].O.C(C)(=O)O | 5 | 0.083333 | COc1ccc(CCCN2C(=O)NCC2c2ccc(OC)cc2)cc1>[Zn].O.C(C)(=O)O>COc1ccc(CCCN2C(=O)N(N)CC2c2ccc(OC)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-77747453736c49cdb794f9713a81a45d | COc1ccc(CCN2C(=O)N(N)CC2c2ccc(C3CC3)cc2)cc1.O=C(CS(=O)(=O)Cl)OCC1c2ccccc2-c2ccccc21>>COc1ccc(CCN2C(=O)N(NS(=O)(=O)CC(=O)OCC3c4ccccc4-c4ccccc43)CC2c2ccc(C3CC3)cc2)cc1 | C1(=CC=C(C=C1)S(=O)(=O)O)C.NN1C(N(C(C1)C1=CC=C(C=C1)C1CC1)CCC1=CC=C(C=C1)OC)=O.CN1CCOCC1.ClS(=O)(=O)CC(=O)OCC1C2=CC=CC=C2C=2C=CC=CC12>>C1=CC=CC=2C3=CC=CC=C3C(C12)COC(CS(=O)(=O)NN1C(N(C(C1)C1=CC=C(C=C1)C1CC1)CCC1=CC=C(C=C1)OC)=O)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[C:10](=[O:11])[N:12]([NH2:13])[CH2:35][CH:36]2[c:37]2[cH:38][cH:39][c:40]([CH:41]3[CH2:42][CH2:43]3)[cH:44][cH:45]2)[cH:46][cH:47]1.Cl[S:14](=[O:15])(=[O:16])[CH2:17][C:18](=[O:19])[O:20][CH2:21][CH:22]1[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2-[c:29]2[cH:30][cH... | COc1ccc(CCN2C(=O)N(N)CC2c2ccc(C3CC3)cc2)cc1.O=C(CS(=O)(=O)Cl)OCC1c2ccccc2-c2ccccc21 | COc1ccc(CCN2C(=O)N(NS(=O)(=O)CC(=O)OCC3c4ccccc4-c4ccccc43)CC2c2ccc(C3CC3)cc2)cc1 | null | null | ClCCl | Acylation | OtherReaction | 1d7782d13faad590a954d6d254ec5fc1e568084640ff236ac5cf433eecd9384e | 53d94e045a6cc897b7aa22bd88fc0cbf2a5e03cfb9e60b6d258d000dc8961a94 | O=C(CS(=O)(=O)NN1CC(c2ccc(C3CC3)cc2)N(CCc2ccccc2)C1=O)OCC1c2ccccc2-c2ccccc21 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8].[C:9]-[#7:10]1-[C:11]-[C:12]-[#7:13](-[NH2;D1;+0:14])-[C:15]-1=[O;D1;H0:16]>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[C:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:14]-[#7:13]1-[C:12]-[C:11]-[#7:10](-[C:9])-[C:15]-1=[O;D1;H0:16] | null | [] | null | null | 45 | MINUTE | To a solution of 1-amino-3-[2-(4-methoxyphenyl)ethyl]-4-(4-cyclopropylphenyl)-2-imidazolidinone p-toluenesulfonic acid salt (2.61 g, 0.0050 mol), dichloromethane (12 mL), and N-methylmorpholine (1.53 mL, 0.014 mol) is added a solution of 9H-fluoren-9-ylmethyl chlorosulfonylacetate, 14, (1.76 g, 0.0052 mol) in dichlorom... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1C[NH]C[NH]1.c1ccccc1.C1CC1.c1ccc2c(c1)Cc1ccccc12 | HCl | ClCCl | null | 0.75 | COc1ccc(CCN2C(=O)N(N)CC2c2ccc(C3CC3)cc2)cc1.O=C(CS(=O)(=O)Cl)OCC1c2ccccc2-c2ccccc21>ClCCl>COc1ccc(CCN2C(=O)N(NS(=O)(=O)CC(=O)OCC3c4ccccc4-c4ccccc43)CC2c2ccc(C3CC3)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e2a4c63e0e94f11b63e83d338fffb8a | COc1ccc(CCN2C(=O)N(NS(=O)(=O)CC(=O)OCC3c4ccccc4-c4ccccc43)CC2c2ccc(C3CC3)cc2)cc1>>COc1ccc(CCN2C(=O)N(NS(=O)(=O)CC(=O)O)CC2c2ccc(C3CC3)cc2)cc1 | C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)CS(=O)(=O)NN1C(N(C(C1)C1=CC=C(C=C1)C1CC1)CCC1=CC=C(C=C1)OC)=O.CCCCCCC=CCCC>>C1(CC1)C1=CC=C(C=C1)C1N(C(N(C1)NS(=O)(=O)CC(=O)O)=O)CCC1=CC=C(C=C1)OC | c1ccc2c(c1)-c1ccccc1C2C[O:20][C:18]([CH2:17][S:14]([NH:13][N:12]1[C:10](=[O:11])[N:9]([CH2:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:33][cH:32]2)[CH:22]([c:23]2[cH:24][cH:25][c:26]([CH:27]3[CH2:28][CH2:29]3)[cH:30][cH:31]2)[CH2:21]1)(=[O:15])=[O:16])=[O:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:... | COc1ccc(CCN2C(=O)N(NS(=O)(=O)CC(=O)OCC3c4ccccc4-c4ccccc43)CC2c2ccc(C3CC3)cc2)cc1 | COc1ccc(CCN2C(=O)N(NS(=O)(=O)CC(=O)O)CC2c2ccc(C3CC3)cc2)cc1 | null | null | CN(C)C=O | Deprotection | Ester saponification (alkyl deprotection) | d3b7b3cabb71120173ac440069c5202e6ad085630bbdda45bf6a334bdc5d7bc8 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1NCC(c2ccc(C3CC3)cc2)N1CCc1ccccc1 | [C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1>>[C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4] | 73.6 | [{"value": 73.6, "product": "C1(CC1)C1=CC=C(C=C1)C1N(C(N(C1)NS(=O)(=O)CC(=O)O)=O)CCC1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 1-[[(9H-fluoren-9-ylmethyloxy)carbonylmethyl]sulfonylamino]-3-[2-(4-methoxyphenyl)ethyl]-4-(4-cyclopropylphenyl)-2-imidazolidinone (2.0 g, 0.0031 mol) in DMF (15 mL) at room temperature is added 1,8-diazabycyclo[5.4.0]undec-7-ene (0.35 mL). The reaction is stirred for approximately one hour, diluted wi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccc2c(c1)Cc1ccccc12 | null | c1ccccc1.C1C[NH]C[NH]1.c1ccccc1.C1CC1 | Other | CN(C)C=O | null | 1 | COc1ccc(CCN2C(=O)N(NS(=O)(=O)CC(=O)OCC3c4ccccc4-c4ccccc43)CC2c2ccc(C3CC3)cc2)cc1>CN(C)C=O>COc1ccc(CCN2C(=O)N(NS(=O)(=O)CC(=O)O)CC2c2ccc(C3CC3)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e392c2c3ee674463b1d55d2a154a1447 | COc1ccc(CCN2C(=O)N(N)CC2c2ccc(OC)cc2)cc1.O=S(=O)(Cl)c1cccnc1>>COc1ccc(CCN2C(=O)N(NS(=O)(=O)c3cccnc3)CC2c2ccc(OC)cc2)cc1 | C=1(C(=CC=CC1)S(=O)(=O)O)C.NN1C(N(C(C1)C1=CC=C(C=C1)OC)CCC1=CC=C(C=C1)OC)=O.Cl.N1=CC(=CC=C1)S(=O)(=O)Cl.CN1CCOCC1>>N1=CC(=CC=C1)S(=O)(=O)NN1C(N(C(C1)C1=CC=C(C=C1)OC)CCC1=CC=C(C=C1)OC)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[C:10](=[O:11])[N:12]([NH2:13])[CH2:23][CH:24]2[c:25]2[cH:26][cH:27][c:28]([O:29][CH3:30])[cH:31][cH:32]2)[cH:33][cH:34]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][n:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[C:10](=[O:11])[... | COc1ccc(CCN2C(=O)N(N)CC2c2ccc(OC)cc2)cc1.O=S(=O)(Cl)c1cccnc1 | COc1ccc(CCN2C(=O)N(NS(=O)(=O)c3cccnc3)CC2c2ccc(OC)cc2)cc1 | null | null | ClCCl | Acylation | OtherReaction | 1d7782d13faad590a954d6d254ec5fc1e568084640ff236ac5cf433eecd9384e | 53d94e045a6cc897b7aa22bd88fc0cbf2a5e03cfb9e60b6d258d000dc8961a94 | O=C1N(NS(=O)(=O)c2cccnc2)CC(c2ccccc2)N1CCc1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[C:9]-[#7:10]1-[C:11]-[C:12]-[#7:13](-[NH2;D1;+0:14])-[C:15]-1=[O;D1;H0:16]>>[C:9]-[#7:10]1-[C:11]-[C:12]-[#7:13](-[NH;D2;+0:14]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8])-[C:15]-1=[O;D1;H0:16] | 42.9 | [{"value": 41.0, "product": "N1=CC(=CC=C1)S(=O)(=O)NN1C(N(C(C1)C1=CC=C(C=C1)OC)CCC1=CC=C(C=C1)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.9, "product": "N1=CC(=CC=C1)S(=O)(=O)NN1C(N(C(C1)C1=CC=C(C=C1)OC)CCC1=CC=C(C=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 1-Amino-3-[2-(4-methoxyphenyl)ethyl]-4-(4-methoxyphenyl)-2-imidazolidinone toluenesulfonic acid (0.3 g, 0.58 mmol) is stirred in dichloromethane (6 mL) and 3-pyridylsulfonylchloride HCl (135 mg, 0.63 mmol) is added followed by 4-methylmorpholine (0.2 mL). The mixture is heated in a microwave oven at 80° C. for 25 minut... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1C[NH]C[NH]1.c1ccncc1.c1ccccc1 | HCl | ClCCl | 80 | null | COc1ccc(CCN2C(=O)N(N)CC2c2ccc(OC)cc2)cc1.O=S(=O)(Cl)c1cccnc1>ClCCl>COc1ccc(CCN2C(=O)N(NS(=O)(=O)c3cccnc3)CC2c2ccc(OC)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe5f5e1e24c946f984ca9e9c09b48ce5 | CC(=O)Cl.COc1ccc(CCN2C(=O)N(N)CC2c2ccc(C)c(C)c2)cc1>>COc1ccc(CCN2C(=O)N(NC(C)=O)CC2c2ccc(C)c(C)c2)cc1 | Cl.NN1C(N(C(C1)C1=CC(=C(C=C1)C)C)CCC1=CC=C(C=C1)OC)=O.C(C)N(CC)CC.C(C)(=O)Cl>>C(C)(=O)NN1C(N(C(C1)C1=CC(=C(C=C1)C)C)CCC1=CC=C(C=C1)OC)=O | Cl[C:14]([CH3:15])=[O:16].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[C:10](=[O:11])[N:12]([NH2:13])[CH2:17][CH:18]2[c:19]2[cH:20][cH:21][c:22]([CH3:23])[c:24]([CH3:25])[cH:26]2)[cH:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[C:10](=[O:11])[N:12]([NH:13][C:14]([CH3:15])=[O:16])[CH... | CC(=O)Cl.COc1ccc(CCN2C(=O)N(N)CC2c2ccc(C)c(C)c2)cc1 | COc1ccc(CCN2C(=O)N(NC(C)=O)CC2c2ccc(C)c(C)c2)cc1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | e9c0e57fff756e07b8f823de2eed1eeaae995a83400f2b5e18582349988c9a5f | 384006bf8ba751654aef497f42d95dd6fc64342c355d6ce7d0ea9a3aaffeacc6 | O=C1NCC(c2ccccc2)N1CCc1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[#7:5]1-[C:6]-[C:7]-[#7:8](-[NH2;D1;+0:9])-[C:10]-1=[O;D1;H0:11]>>[C:4]-[#7:5]1-[C:6]-[C:7]-[#7:8](-[NH;D2;+0:9]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:10]-1=[O;D1;H0:11] | 78 | [{"value": 78.0, "product": "C(C)(=O)NN1C(N(C(C1)C1=CC(=C(C=C1)C)C)CCC1=CC=C(C=C1)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.7, "product": "C(C)(=O)NN1C(N(C(C1)C1=CC(=C(C=C1)C)C)CCC1=CC=C(C=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | A solution of compound 1-amino-3-[2-(4-methoxy-phenyl)ethyl]-4-(3,4-dimethylphenyl)-2-imidazolidinone hydrochloride (300 mg, 0.80 mmol) in dichloromethane (3.0 mL) is cooled in an ice bath and triethylamine (0.26 mL, 1.8 mmol) is added, followed by dropwise addition of acetyl chloride (0.068 mL, 0.96 mmol). The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acylhydrazine | Acylhydrazine.Acylhydrazine | null | null | c1ccccc1.C1C[NH]C[NH]1.c1ccccc1 | HCl | ClCCl | null | 0.75 | CC(=O)Cl.COc1ccc(CCN2C(=O)N(N)CC2c2ccc(C)c(C)c2)cc1>ClCCl>COc1ccc(CCN2C(=O)N(NC(C)=O)CC2c2ccc(C)c(C)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-26b9fe0e3007440bab82313a178aeab4 | COc1ccc(CCN2C(=O)N(N)CC2c2ccc(C)c(C)c2)cc1.N#Cc1ccc(C=O)cc1>>COc1ccc(CCN2C(=O)N(NCc3ccc(C#N)cc3)CC2c2ccc(C)c(C)c2)cc1 | C(=O)(O)[O-].[Na+].Cl.NN1C(N(C(C1)C1=CC(=C(C=C1)C)C)CCC1=CC=C(C=C1)OC)=O.C(#N)C1=CC=C(C=O)C=C1.[BH3-]C#N.[Na+]>>C(#N)C1=CC=C(C=C1)CNN1C(N(C(C1)C1=CC(=C(C=C1)C)C)CCC1=CC=C(C=C1)OC)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[C:10](=[O:11])[N:12]([NH2:13])[CH2:23][CH:24]2[c:25]2[cH:26][cH:27][c:28]([CH3:29])[c:30]([CH3:31])[cH:32]2)[cH:33][cH:34]1.O=[CH:14][c:15]1[cH:16][cH:17][c:18]([C:19]#[N:20])[cH:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[C:10](=[O:11])... | COc1ccc(CCN2C(=O)N(N)CC2c2ccc(C)c(C)c2)cc1.N#Cc1ccc(C=O)cc1 | COc1ccc(CCN2C(=O)N(NCc3ccc(C#N)cc3)CC2c2ccc(C)c(C)c2)cc1 | null | null | O.C(C)(=O)O.C(C)(=O)OCC.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | dc689e6b884b4134f84d1fd26a965cadf5d14786fd8a8f3384ce2a1a986845e5 | 0f16807814c31902dff5230c73ab8d897e3cfa921d886582e67718c7f1350535 | O=C1N(NCc2ccccc2)CC(c2ccccc2)N1CCc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6]1-[C:7]-[C:8]-[#7:9](-[NH2;D1;+0:10])-[C:11]-1=[O;D1;H0:12]>>[C:5]-[#7:6]1-[C:7]-[C:8]-[#7:9](-[NH;D2;+0:10]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:11]-1=[O;D1;H0:12] | 40 | [{"value": 40.0, "product": "C(#N)C1=CC=C(C=C1)CNN1C(N(C(C1)C1=CC(=C(C=C1)C)C)CCC1=CC=C(C=C1)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.5, "product": "C(#N)C1=CC=C(C=C1)CNN1C(N(C(C1)C1=CC(=C(C=C1)C)C)CCC1=CC=C(C=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 1-amino-3-[2-(4-methoxy-phenyl)ethyl]-4-(3,4-dimethylphenyl)-2-imidazolidinone hydrochloride (350 mg, 0.93 mmol), THF (4.5 mL), and 4-cyanobenzaldehyde (131 mg, 1.0 mmol) is stirred at 50° C. for 30 minutes, then cooled in an ice bath and glacial acetic acid (3.5 mL) is added. To the resulting mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Aldehyde | Acylhydrazine | null | null | c1ccccc1.C1C[NH]C[NH]1.c1ccccc1.c1ccccc1 | Other | O.C(C)(=O)O.C(C)(=O)OCC.C1CCOC1 | null | 2 | COc1ccc(CCN2C(=O)N(N)CC2c2ccc(C)c(C)c2)cc1.N#Cc1ccc(C=O)cc1>O.C(C)(=O)O.C(C)(=O)OCC.C1CCOC1>COc1ccc(CCN2C(=O)N(NCc3ccc(C#N)cc3)CC2c2ccc(C)c(C)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee58c4eb028248dbac4fa8b5ddb7daab | COc1ccc(CCN2C(=O)N(N(Cc3ccncc3)C(=O)CC(C)(C)C)CC2c2ccc(C)c(C)c2)cc1>>COc1ccc(CCN2C(=O)N(NCc3ccncc3)CC2c2ccc(C)c(C)c2)cc1 | CC=1C=C(C=CC1C)C1N(C(N(C1)N(C(CC(C)(C)C)=O)CC1=CC=NC=C1)=O)CCC1=CC=C(C=C1)OC.C(C)[SiH](CC)CC.FC(C(=O)O)(F)F>>CC=1C=C(C=CC1C)C1N(C(N(C1)NCC1=CC=NC=C1)=O)CCC1=CC=C(C=C1)OC | CC(C)(C)CC(=O)[N:13]([N:12]1[C:10](=[O:11])[N:9]([CH2:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:32][cH:31]2)[CH:22]([c:23]2[cH:24][cH:25][c:26]([CH3:27])[c:28]([CH3:29])[cH:30]2)[CH2:21]1)[CH2:14][c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[C:10](=[O:11])[... | COc1ccc(CCN2C(=O)N(N(Cc3ccncc3)C(=O)CC(C)(C)C)CC2c2ccc(C)c(C)c2)cc1 | COc1ccc(CCN2C(=O)N(NCc3ccncc3)CC2c2ccc(C)c(C)c2)cc1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of tertiary amines | ceed3f5050850f6a35aa607e68a2954f707b86e70e8d191f84a6b9663a4f1df9 | c2cd32101c8ac07c536b0552d5e7106097880e67be7cc4b9c42843814449133e | O=C1N(NCc2ccncc2)CC(c2ccccc2)N1CCc1ccccc1 | C-C(-C)(-C)-C-C(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3])-[#7:4](-[C:5])-[C:6](=[O;D1;H0:7])-[#7:8]>>[#7:8]-[C:6](=[O;D1;H0:7])-[#7:4](-[NH;D2;+0:1]-[C:2]-[c:3])-[C:5] | 104.7 | [{"value": 76.0, "product": "CC=1C=C(C=CC1C)C1N(C(N(C1)NCC1=CC=NC=C1)=O)CCC1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.7, "product": "CC=1C=C(C=CC1C)C1N(C(N(C1)NCC1=CC=NC=C1)=O)CCC1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | A solution of N-{4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxo-imidazolidin-1-yl}-3,3-dimethyl-N-pyridin-4-ylmethyl-butyramide (205 mg, 0.386 mmol) in CH2Cl2 (1.5 mL) is cooled in an ice bath and triethylsilane (0.129 mL, 0.81 mmol) is added, followed by trifluoroacetic acid (1.5 mL). The ice bath is remove... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | Acylhydrazine | null | null | c1ccccc1.C1C[NH]C[NH]1.c1ccncc1.c1ccccc1 | HO- | C(Cl)Cl | null | 2.5 | COc1ccc(CCN2C(=O)N(N(Cc3ccncc3)C(=O)CC(C)(C)C)CC2c2ccc(C)c(C)c2)cc1>C(Cl)Cl>COc1ccc(CCN2C(=O)N(NCc3ccncc3)CC2c2ccc(C)c(C)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd20c2f31fb0433fb0efbb3a90109058 | COc1ccc(CC(=O)Cl)cc1.COc1ccc([C@@H](N)C(N)=O)cc1>>COc1ccc(CC(=O)N[C@@H](C(N)=O)c2ccc(OC)cc2)cc1 | O.N[C@@H](C(=O)N)C1=CC=C(C=C1)OC.C(C)N(CC)CC.COC1=CC=C(C=C1)CC(=O)Cl>>COC1=CC=C(C=C1)[C@H](C(=O)N)NC(CC1=CC=C(C=C1)OC)=O | Cl[C:8]([CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:24][cH:23]1)=[O:9].[NH2:10][C@@H:11]([C:12]([NH2:13])=[O:14])[c:15]1[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8](=[O:9])[NH:10][C@@H:11]([C:12]([NH2:13])=[O:14])[c:15]2[cH:16][cH:17][c:18]([O:19][CH3:20])[cH... | COc1ccc(CC(=O)Cl)cc1.COc1ccc([C@@H](N)C(N)=O)cc1 | COc1ccc(CC(=O)N[C@@H](C(N)=O)c2ccc(OC)cc2)cc1 | null | null | CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Cc1ccccc1)NCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[N;D1;H2:5]-[C:6](=[O;D1;H0:7])-[C:8](-[NH2;D1;+0:9])-[c:10]>>[N;D1;H2:5]-[C:6](=[O;D1;H0:7])-[C:8](-[c:10])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | 89 | [{"value": 89.0, "product": "COC1=CC=C(C=C1)[C@H](C(=O)N)NC(CC1=CC=C(C=C1)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.9, "product": "COC1=CC=C(C=C1)[C@H](C(=O)N)NC(CC1=CC=C(C=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A solution of (R)-2-amino-2-(4-methoxyphenyl)acetamide (200 g, 1.11 mol), triethylamine (124 g, 1.22 mol) in dimethylformamide (2 L) is cooled to 5° C. in an ice bath and (4-methoxyphenyl)acetyl chloride (225 g, 187 mL, 1.22 mol) is added dropwise at a rate which maintains the temperature in a range from 5° C. to 7° C.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | CN(C=O)C | null | 1.5 | COc1ccc(CC(=O)Cl)cc1.COc1ccc([C@@H](N)C(N)=O)cc1>CN(C=O)C>COc1ccc(CC(=O)N[C@@H](C(N)=O)c2ccc(OC)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-efd2d005c4974fceb69e34e9a02f044a | COc1ccc(CC(=O)N[C@@H](C(N)=O)c2ccc(OC)cc2)cc1>>COc1ccc(CCN[C@@H](CN)c2ccc(OC)cc2)cc1 | [OH-].[Na+].CSC.B.COC1=CC=C(C=C1)[C@H](C(=O)N)NC(CC1=CC=C(C=C1)OC)=O.Cl>>COC1=CC=C(C=C1)[C@H](CN)NCCC1=CC=C(C=C1)OC | O=[C:8]([CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22][cH:21]1)[NH:9][C@@H:10]([C:11](=O)[NH2:12])[c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][C@@H:10]([CH2:11][NH2:12])[c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][cH:20]2)[cH:21][cH:22]1 | COc1ccc(CC(=O)N[C@@H](C(N)=O)c2ccc(OC)cc2)cc1 | COc1ccc(CCN[C@@H](CN)c2ccc(OC)cc2)cc1 | null | null | O.C(Cl)Cl.C1CCOC1 | Reduction | OtherReaction | 04e43694977500644d0b633fb755e407fa4ef4bbf642031ff37112cef5da0b19 | 0be5ea9a8858a6554cb4f68acf3e53a0cda8aaf13d02d27311e5afd5d7b4e8fd | c1ccc(CCNCc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[N;D1;H2:2])-[C:3](-[c:4])-[#7:5]-[C;H0;D3;+0:6](=O)-[C:7]-[c:8]>>[N;D1;H2:2]-[CH2;D2;+0:1]-[C:3](-[c:4])-[#7:5]-[CH2;D2;+0:6]-[C:7]-[c:8] | 104.7 | [{"value": 104.7, "product": "COC1=CC=C(C=C1)[C@H](CN)NCCC1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-(R)-(4-methoxyphenyl)-2-[2-(4-methoxyphenyl)-acetylamino]-acetamide (316 g, 0.96 mol) in THF (2 L) is heated to 35° C. and borane dimethyl sulfide (428 mL, 4.28 mol) is added over approximately 1 hour after which the reaction is heated to reflux for 18 hours. After cooling the reaction solution to 8° C.... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Secondary amide | null | null | null | c1ccccc1.c1ccccc1 | Other | O.C(Cl)Cl.C1CCOC1 | null | null | COc1ccc(CC(=O)N[C@@H](C(N)=O)c2ccc(OC)cc2)cc1>O.C(Cl)Cl.C1CCOC1>COc1ccc(CCN[C@@H](CN)c2ccc(OC)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-89730026afe84821898c198094e13e2c | COc1ccc(CCN[C@@H](CN)c2ccc(OC)cc2)cc1.O=C(n1ccnc1)n1ccnc1>>COc1ccc(CCN2C(=O)NC[C@H]2c2ccc(OC)cc2)cc1 | Cl.COC1=CC=C(C=C1)[C@H](CN)NCCC1=CC=C(C=C1)OC.C(=O)(N1C=NC=C1)N1C=NC=C1>>COC1=CC=C(C=C1)[C@@H]1CNC(N1CCC1=CC=C(C=C1)OC)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][C@@H:14]([CH2:13][NH2:12])[c:15]2[cH:16][cH:17][c:18]([O:19][CH3:20])[cH:21][cH:22]2)[cH:23][cH:24]1.c1cn([C:10](n2ccnc2)=[O:11])cn1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[C:10](=[O:11])[NH:12][CH2:13][C@H:14]2[c:15]2[cH:16][cH:17][c:18]([O:19]... | COc1ccc(CCN[C@@H](CN)c2ccc(OC)cc2)cc1.O=C(n1ccnc1)n1ccnc1 | COc1ccc(CCN2C(=O)NC[C@H]2c2ccc(OC)cc2)cc1 | null | null | [Cl-].[Na+].O.C(C)(=O)OCC | Acylation | OtherReaction | d50ab08ba9b21e12798143263731d8e47a5fd3f51bea1aefeed0abbfa63d5047 | 092fb1988ce3c31a0210cc9ec123f317c79841c29a05a3f2098134944f12c379 | O=C1NC[C@@H](c2ccccc2)N1CCc1ccccc1 | [C:1]-[C:2]-[NH;D2;+0:3]-[C:4](-[c:5])-[C:6]-[NH2;D1;+0:7].[O;D1;H0:8]=[C;H0;D3;+0:9](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C:4](-[c:5])-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:9]-1=[O;D1;H0:8] | 96.9 | [{"value": 96.0, "product": "COC1=CC=C(C=C1)[C@@H]1CNC(N1CCC1=CC=C(C=C1)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.9, "product": "COC1=CC=C(C=C1)[C@@H]1CNC(N1CCC1=CC=C(C=C1)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-(R)-(4-methoxyphenyl)-N1-[2-(4-methoxyphenyl)ethyl]ethane-1,2-diamine (446 g, 1.48 mol) in ethyl acetate (2.25 L) is placed in a water bath and 1,1′-carbonyldiimidazole (264 g, 1.62 mol) is added in portions. The reaction is then heated to reflux for 1.5 hours after which the solution is cooled, treated... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | C1C[NH]CN1 | c1ccccc1.C1C[NH]CN1.c1ccccc1 | Other | [Cl-].[Na+].O.C(C)(=O)OCC | null | null | COc1ccc(CCN[C@@H](CN)c2ccc(OC)cc2)cc1.O=C(n1ccnc1)n1ccnc1>[Cl-].[Na+].O.C(C)(=O)OCC>COc1ccc(CCN2C(=O)NC[C@H]2c2ccc(OC)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b34076ae389d4507b8b9606ddb0eccac | COc1ccc(CCN2C(=O)N(N)C[C@H]2c2ccc(OC)cc2)cc1.CS(=O)(=O)Cl>>COc1ccc(CCN2C(=O)N(NS(C)(=O)=O)C[C@H]2c2ccc(OC)cc2)cc1 | CS(=O)(=O)Cl.NN1C(N([C@@H](C1)C1=CC=C(C=C1)OC)CCC1=CC=C(C=C1)OC)=O.N1=CC=CC=C1>>CS(=O)(=O)NN1C(N([C@@H](C1)C1=CC=C(C=C1)OC)CCC1=CC=C(C=C1)OC)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[C:10](=[O:11])[N:12]([NH2:13])[CH2:18][C@H:19]2[c:20]2[cH:21][cH:22][c:23]([O:24][CH3:25])[cH:26][cH:27]2)[cH:28][cH:29]1.Cl[S:14]([CH3:15])(=[O:16])=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][N:9]2[C:10](=[O:11])[N:12]([NH:13][S:14]([CH3:15])(=[O... | COc1ccc(CCN2C(=O)N(N)C[C@H]2c2ccc(OC)cc2)cc1.CS(=O)(=O)Cl | COc1ccc(CCN2C(=O)N(NS(C)(=O)=O)C[C@H]2c2ccc(OC)cc2)cc1 | null | null | ClCCl | Acylation | OtherReaction | 1d7782d13faad590a954d6d254ec5fc1e568084640ff236ac5cf433eecd9384e | 53d94e045a6cc897b7aa22bd88fc0cbf2a5e03cfb9e60b6d258d000dc8961a94 | O=C1NC[C@@H](c2ccccc2)N1CCc1ccccc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[#7:6]1-[C:7]-[C:8]-[#7:9](-[NH2;D1;+0:10])-[C:11]-1=[O;D1;H0:12]>>[C:5]-[#7:6]1-[C:7]-[C:8]-[#7:9](-[NH;D2;+0:10]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:11]-1=[O;D1;H0:12] | 75 | [{"value": 75.0, "product": "CS(=O)(=O)NN1C(N([C@@H](C1)C1=CC=C(C=C1)OC)CCC1=CC=C(C=C1)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | A solution of 1-amino-3-[2-(4-methoxyphenyl)-ethyl]-4-(R)-(4-methoxyphenyl)-2-imidazolidinone (247 g, 0.72 mol) in dichloromethane (2.35 L) and pyridine (174 mL, 2.15 mol) is cooled in an ice bath to 18° C. Methanesulfonyl chloride (73 mL, 0.94 mol) is added dropwise. The reaction is stirred cold for 2.5 hours then was... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.C1C[NH]C[NH]1.c1ccccc1 | HCl | ClCCl | null | 2.5 | COc1ccc(CCN2C(=O)N(N)C[C@H]2c2ccc(OC)cc2)cc1.CS(=O)(=O)Cl>ClCCl>COc1ccc(CCN2C(=O)N(NS(C)(=O)=O)C[C@H]2c2ccc(OC)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb58f2ccff594f4098f7a85cddd60ef3 | CC(=O)c1cc(O)ccc1O.CCCI>>CCCOc1ccc(O)c(C(C)=O)c1 | CC(=O)C1=C(C=CC(=C1)O)O.C(=O)([O-])[O-].[K+].[K+].C(CC)I>>OC1=C(C=C(C=C1)OCCC)C(C)=O | [OH:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([C:11]([CH3:12])=[O:13])[cH:14]1.I[CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[c:10]([C:11]([CH3:12])=[O:13])[cH:14]1 | CC(=O)c1cc(O)ccc1O.CCCI | CCCOc1ccc(O)c(C(C)=O)c1 | null | null | CC(=O)C.C(Cl)(Cl)Cl.CCOC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | I-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 89.3 | [{"value": 89.3, "product": "OC1=C(C=C(C=C1)OCCC)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 10 g of 2,5-dihydroxyacetophenone suspended in 100 ml of acetone are placed in a 500 ml round-bottomed flask and 9.14 g of anhydrous K2CO3 are added, followed by addition of 12.4 g of propyl iodide. The reaction medium is refluxed for 30 hours. After cooling to room temperature, the medium is filtered through Celite® a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HI | CC(=O)C.C(Cl)(Cl)Cl.CCOC(=O)C | null | null | CC(=O)c1cc(O)ccc1O.CCCI>CC(=O)C.C(Cl)(Cl)Cl.CCOC(=O)C>CCCOc1ccc(O)c(C(C)=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-00c2832e1d7d435798cbf6b75d1754c1 | CC(=O)OC(C)=O.CCCCc1ccc(O)cc1>>CCCCc1ccc(OC(C)=O)cc1 | CCCCC=1C=CC(=CC1)O.CC(=O)OC(=O)C.N1=CC=CC=C1>>C(C)(=O)OC1=CC=C(C=C1)CCCC | CC(=O)O[C:10]([CH3:11])=[O:12].[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:13][cH:14]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][C:10]([CH3:11])=[O:12])[cH:13][cH:14]1 | CC(=O)OC(C)=O.CCCCc1ccc(O)cc1 | CCCCc1ccc(OC(C)=O)cc1 | null | null | ClCCl | Acylation | Acetic anhydride and alcohol to ester | 55f321cc520ab80a97c517ea4db1ffe6ba0ea312e2db70f74b0966421bec0a44 | 96218bff9f96200922f4dff3481116557fe6986cba41ef7bff8cc8a0b43bd224 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 2 | HOUR | A solution of 10 g of 4-n-butylphenol, 10 ml of Ac2O and 8 ml of pyridine is stirred at reflux in 10 ml of dichloromethane. After 2 hours, the medium is cooled to room temperature, diluted with dichloromethane, washed with water, washed with 1M HCl solution, washed with saturated CuSO4 solution, washed with water and d... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol | Ester | null | null | c1ccccc1 | HO- | ClCCl | null | 2 | CC(=O)OC(C)=O.CCCCc1ccc(O)cc1>ClCCl>CCCCc1ccc(OC(C)=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe3059a5e2924c2891b8309964868356 | Cc1ccccc1.O=C([O-])C(F)(F)C(F)(F)F>>COc1ccc(C(F)(F)C(F)(F)F)cc1 | FC(C(C(=O)[O-])(F)F)(F)F.[K+].CN(C)C=O.C1(=CC=CC=C1)C>>COC1=CC=C(C=C1)C(C(F)(F)F)(F)F | c1[cH:5][cH:4][c:3]([CH3:1])[cH:15][cH:14]1.O=[C:6]([O-:2])[C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[F:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1 | Cc1ccccc1.O=C([O-])C(F)(F)C(F)(F)F | COc1ccc(C(F)(F)C(F)(F)F)cc1 | null | [Cu]I | null | Heteroatom Alkylation and Arylation | OtherReaction | cbbc4638d115b7ee7ae7ec7dbbd47b205d49359ed05e1559cd11cd47125e8d2e | 4872557aad018a5da67162c8c3d3939f17f713d6f4190285b52663574dbc6c51 | c1ccccc1 | O=[C;H0;D3;+0:1](-[O-;H0;D1:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[C:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9].[CH3;D1;+0:10]-[c;H0;D3;+0:11]1:[c:12]:[cH;D2;+0:13]:c:[cH;D2;+0:14]:[c:15]:1>>[CH3;D1;+0:10]-[O;H0;D2;+0:2]-[c;H0;D3;+0:11]1:[c:12]:[cH;D2;+0:13]:[c;H0;D3;+0:1](-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[C:6](-[F;D... | null | [] | 140 | CELSIUS | null | null | 8.3 g of potassium pentafluoropropionate and 9.8 g of CuI are introduced into a 500 ml three-necked flask equipped with Dean-Stark apparatus and a condenser, under an inert atmosphere. 90 ml of DMF and 110 ml of toluene are added. The medium is heated to 140° C. under nitrogen and 80 ml of toluene are distilled off. Th... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | [Cu]I | 140 | null | Cc1ccccc1.O=C([O-])C(F)(F)C(F)(F)F>[Cu]I>COc1ccc(C(F)(F)C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-90d7ef64429c415dae25b6d9e70f1340 | CC(=O)Cl.COc1ccc(C(F)(F)C(F)(F)F)cc1>>COc1ccc(C(F)(F)C(F)(F)F)cc1C(C)=O | C(C)(=O)Cl.[Li]CCCC.COC1=CC=C(C=C1)C(C(F)(F)F)(F)F>>COC1=C(C=C(C=C1)C(C(F)(F)F)(F)F)C(C)=O | Cl[C:16]([CH3:17])=[O:18].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[F:13])[cH:14][c:15]1[C:16]([CH3:17])=[O:18] | CC(=O)Cl.COc1ccc(C(F)(F)C(F)(F)F)cc1 | COc1ccc(C(F)(F)C(F)(F)F)cc1C(C)=O | null | [Cl-].[Zn+2].[Cl-] | CCCCCC.CCOCC.C1CCOC1 | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#8:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[#8:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[c:8]:[c:9] | null | [] | -70 | CELSIUS | 30 | MINUTE | 7.4 ml of BuLi at 2.5M in hexane are added, at −70° C., to a solution of 3.5 g of 1-methoxy-4-pentafluoroethylbenzene in 50 ml of anhydrous THF. The medium is stirred for 30 minutes at −70° C. and then for 45 minutes at 0° C. 15.5 ml of a 1M solution of zinc chloride in ether are then added. After stirring for 10 minut... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | [Cl-].[Zn+2].[Cl-].CCCCCC.CCOCC.C1CCOC1 | -70 | 0.5 | CC(=O)Cl.COc1ccc(C(F)(F)C(F)(F)F)cc1>[Cl-].[Zn+2].[Cl-].CCCCCC.CCOCC.C1CCOC1>COc1ccc(C(F)(F)C(F)(F)F)cc1C(C)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36cabad3c13f4f819dd6cafb2210ee4e | NC1CCN(Cc2ccccc2)CC1.O=C1CCOCC1>>c1ccc(CN2CCC(NC3CCOCC3)CC2)cc1 | NC1CCN(CC1)CC1=CC=CC=C1.C(=O)([O-])[O-].[Na+].[Na+].O1CCC(CC1)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>C(C1=CC=CC=C1)N1CCC(CC1)NC1CCOCC1 | [cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][CH:9]([NH2:10])[CH2:17][CH2:18]2)[cH:19][cH:20]1.O=[C:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][CH:9]([NH:10][CH:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[CH2:17][CH2:18]2)[cH:19][cH:20]1 | NC1CCN(Cc2ccccc2)CC1.O=C1CCOCC1 | c1ccc(CN2CCC(NC3CCOCC3)CC2)cc1 | null | null | ClCCCl.CCOC(=O)C | Heteroatom Alkylation and Arylation | Reductive amination with ketone | a62e19dcb64f6ab3f45c1165dbcd05391bd608bb6e9251e489061823f93611dc | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(CN2CCC(NC3CCOCC3)CC2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1.[C:7]-[C:8](-[NH2;D1;+0:9])-[C:10]>>[C:7]-[C:8](-[NH;D2;+0:9]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#8:4]-[C:5]-[C:6]-1)-[C:10] | 85.4 | [{"value": 85.4, "product": "C(C1=CC=CC=C1)N1CCC(CC1)NC1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | 19 g of 4-amino-1-benzylpiperidine are placed in 50 ml of 1,2-dichloroethane under dry nitrogen and 10 g of tetrahydropyran-4-one in 20 ml of 1,2-dichloro-ethane are added; after stirring for 10 minutes, 29.6 g of NaBH(OAc)3 are added and the mixture is then stirred for one day. 10% Na2CO3 solution and EtOAc are added ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CCOCC1 | C1CCOCC1 | c1ccccc1.C1CC[NH]CC1.C1CCOCC1 | Other | ClCCCl.CCOC(=O)C | null | 0.166667 | NC1CCN(Cc2ccccc2)CC1.O=C1CCOCC1>ClCCCl.CCOC(=O)C>c1ccc(CN2CCC(NC3CCOCC3)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5a6210c782834094a795c4f5957bab41 | CCOC(CBr)OCC.COC(=O)c1ccc(O)cc1>>CCOC(COc1ccc(C(=O)OC)cc1)OCC | OC1=CC=C(C(=O)OC)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCC(OCC)OCC>>C(C)OC(COC1=CC=C(C(=O)OC)C=C1)OCC | Br[CH2:5][CH:4]([O:3][CH2:2][CH3:1])[O:17][CH2:18][CH3:19].[OH:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[cH:15][cH:16]1>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[cH:15][cH:16]1)[O:17][CH2:18][CH3:19] | CCOC(CBr)OCC.COC(=O)c1ccc(O)cc1 | CCOC(COc1ccc(C(=O)OC)cc1)OCC | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](-[#8:3])-[#8:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[#8:3]-[C:2](-[#8:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 94.6 | [{"value": 94.6, "product": "C(C)OC(COC1=CC=C(C(=O)OC)C=C1)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | A mixture containing 10 g of methyl 4-hydroxybenzoate and 22.71 g of K2CO3 in 100 ml of THF is heated at 100° C. for 5 min and cooled to room temperature, 15.54 g of 2-bromo-1,1-diethoxyethane are added and the mixture is stirred for 2 hours at room temperature and then for 32 hours at 100° C., and is allowed to return... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | C1CCOC1 | 100 | 2 | CCOC(CBr)OCC.COC(=O)c1ccc(O)cc1>C1CCOC1>CCOC(COc1ccc(C(=O)OC)cc1)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-56d02ca67e6945448b432ec28fca6a04 | CC#N.CCOC(C)=O.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.Nc1nccs1.O=C(O)c1ccc(CCCl)cc1>>CCCCc1ccc(OC)c(-c2csc(NC(=O)c3ccc(CCCl)cc3)n2)c1 | C1=CSC(=N1)N.CCOC(=O)C.CC#N.ClCCC1=CC=C(C(=O)O)C=C1.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C>>C(CCC)C=1C=CC(=C(C1)C=1N=C(SC1)NC(C1=CC=C(C=C1)CCCl)=O)OC | N#[C:2][CH3:1].CC(=O)[O:9][CH2:4][CH3:3].CN(C)[P+](On1nn[c:8]2[cH:7][cH:6][cH:5][cH:29][c:11]12)(N(C)C)N(C)[CH3:10].[cH:12]1[cH:13][s:14][c:15]([NH2:16])[n:28]1.O[C:17](=[O:18])[c:19]1[cH:20][cH:21][c:22]([CH2:23][CH2:24][Cl:25])[cH:26][cH:27]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH3:10])[c:11](-... | CC#N.CCOC(C)=O.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.Nc1nccs1.O=C(O)c1ccc(CCCl)cc1 | CCCCc1ccc(OC)c(-c2csc(NC(=O)c3ccc(CCCl)cc3)n2)c1 | null | null | CCN(CC)CC | Acylation | OtherReaction | a129d4fc0b898432ae1e08d0e260244a16aeed2650819f7291dab4e644ab5442 | 278ded22deb457a818a6290a8bb42ed13463006530e29ce68a54f12dd862b1e0 | O=C(Nc1nc(-c2ccccc2)cs1)c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[CH2;D2;+0:2]-[CH3;D1;+0:3].C-N(-C)-[P+](-O-n1:n:n:[c;H0;D3;+0:4]2:[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c;H0;D3;+0:9]:2:1)(-N(-C)-C)-N(-C)-[CH3;D1;+0:10].N#[C;H0;D2;+0:11]-[C;D1;H3:12].O-[C;H0;D3;+0:13](=[O;D1;H0:14])-[c:15](:[c:16]):[c:17].[NH2;D1;+0:18]-[c:19]1:[#16;a:20]:[c:21]:[cH;D2;+0:22]:[#7;a:... | null | [] | null | null | 48 | HOUR | A mixture containing 3 g of aminothiazole from Preparation 1.2, 10 ml of CH3CN, 2.54 g of 4-(2-chloroethyl)benzoic acid, 1.11 ml of Et3N and 6.1 g of BOP is prepared and stirred for 48 hours. The reaction medium is diluted with EtOAc and then washed with saturated Na2CO3 solution (twice) and with saturated NaCl solutio... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester.Nitrile.Primary amine.Tertiary amine.Tertiary amine.Tertiary amine | Ether.Secondary amide | c1ccc2[nH]nnc2c1.c1cscn1 | c1ccccc1.c1cscn1 | c1ccccc1.c1cscn1.c1ccccc1 | HO- | CCN(CC)CC | null | 48 | CC#N.CCOC(C)=O.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.Nc1nccs1.O=C(O)c1ccc(CCCl)cc1>CCN(CC)CC>CCCCc1ccc(OC)c(-c2csc(NC(=O)c3ccc(CCCl)cc3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a21cda3d25f44f7885ea0a6d5dc02417 | BrCCOC1CCCCO1.COC(=O)c1ccc(O)cc1>>COC(=O)c1ccc(OCCOC2CCCCO2)cc1 | OC1=CC=C(C(=O)OC)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCOC1OCCCC1>>O1C(CCCC1)OCCOC1=CC=C(C(=O)OC)C=C1 | Br[CH2:10][CH2:11][O:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][O:18]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:19][cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][O:12][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:18]2)[cH:19][cH:20]1 | BrCCOC1CCCCO1.COC(=O)c1ccc(O)cc1 | COC(=O)c1ccc(OCCOC2CCCCO2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCCOC2CCCCO2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 105.4 | [{"value": 105.4, "product": "O1C(CCCC1)OCCOC1=CC=C(C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture containing 40 g of methyl 4-hydroxybenzoate and 90.84 g of K2CO3 in 400 ml of DMF is heated to 100° C. and 71.47 g of 2-(2-bromoethoxy)tetrahydro-2H-pyran are added slowly, with continued heating for 8 hours. The inorganic material is filtered off and rinsed with DMF. The filtrate is evaporated under vacuum a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CCOCC1 | HBr | CN(C)C=O | 100 | null | BrCCOC1CCCCO1.COC(=O)c1ccc(O)cc1>CN(C)C=O>COC(=O)c1ccc(OCCOC2CCCCO2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36da2859f9214c56ba8c4ed5b878c3f6 | I>>[I-] | CN(C(=N)N(C)C)C.I>>[I-].CN(C(=N)N(C)C)C | [IH:9]>>[I-:9] | I | [I-] | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [IH;D0;+0:1]>>[I-;H0;D0:1] | null | [] | null | null | null | null | 1,1,3,3-tetramethylguanidine (1.21 g, 10.5 mmol) was dissolved in water (32.8 g). MoO3 (0.225 g, 1.58 mmol) and hydroiodic acid (1.65 g, 7.35 mmol, 57 wt % solution in water) were slowly added to this solution. This yielded a solution of 1,1,3,3-tetramethylguanidine iodide and 1,1,3,3-tetramethylguanidine molybdate wit... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | null | null | I>O>[I-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-167a0f3131e54aa1a7eb1b1d1f0fbb96 | O=C(O)CN(CC(=O)O)CP(=O)(O)O>>O=C(O)CNCP(=O)(O)O | P(=O)(O)(O)CN(CC(=O)O)CC(=O)O.P(=O)(O)(O)CN(CC(=O)O)CC(=O)O.O=O>>P(=O)(O)(O)CNCC(=O)O.P(=O)(O)(O)CN(CC(=O)O)CC(=O)O | O=C(O)C[N:19]([CH2:18][C:16](=[O:15])[OH:17])[CH2:20][P:21](=[O:22])([OH:23])[OH:24]>>[O:15]=[C:16]([OH:17])[CH2:18][NH:19][CH2:20][P:21](=[O:22])([OH:23])[OH:24] | O=C(O)CN(CC(=O)O)CP(=O)(O)O | O=C(O)CNCP(=O)(O)O | null | null | null | Reduction | Hydrogenolysis of tertiary amines | 72a33a1f24033d27534e201c6f7df73bbb43e65f22055b6ffe4c75743279e24d | d5c20295d11b0bf517c91c4a2785038fba42ae44b7ae51b79fc360a0e1a4fb12 | null | O-C(=O)-C-[N;H0;D3;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[O;D1;H1:5])-[C:6]-[#15:7]>>[#15:7]-[C:6]-[NH;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[O;D1;H1:5] | null | [] | null | null | null | null | Many of the various streams shown in FIG. 14A are analogous to those described above for the reaction system shown in FIG. 14 in which the adiabatic crystallizer 319 and the heat-driven evaporative crystallizer 343 are operated in a semi-parallel manner. An aqueous feed stream 301 comprising an N-(phosphonomethyl)imino... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amine | Secondary amine | null | null | null | HO- | null | null | null | O=C(O)CN(CC(=O)O)CP(=O)(O)O>>O=C(O)CNCP(=O)(O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff8c0eb5ff914c889b612fb608cbb1c6 | Clc1cc[c]([Mg][Br])cc1.O=Cc1ccc(Cl)cc1Cl>>OC(c1ccc(Cl)cc1)c1ccc(Cl)cc1Cl | ClC1=C(C=O)C=CC(=C1)Cl.ClC1=CC=C(C=C1)[Mg]Br>>ClC1=C(C(C2=CC=C(C=C2)Cl)O)C=CC(=C1)Cl | [Br][Mg][c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][cH:9]1.[O:1]=[CH:2][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]1[Cl:17]>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]1[Cl:17] | Clc1cc[c]([Mg][Br])cc1.O=Cc1ccc(Cl)cc1Cl | OC(c1ccc(Cl)cc1)c1ccc(Cl)cc1Cl | null | null | C(C)OCC | C-C Coupling | Grignard from aldehyde to alcohol | ad2add9c044125ce717c8f1f747992ed9f3fcddb29e094d415938fed9e82a5d3 | 38fa131ecaada942f85a297b49034b58ccef3f2e8ba6de5e28a59b5f4292ff1f | c1ccc(Cc2ccccc2)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;H0;D1;+0:6]=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[OH;D1;+0:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 73 | [{"value": 73.0, "product": "ClC1=C(C(C2=CC=C(C=C2)Cl)O)C=CC(=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.0, "product": "ClC1=C(C(C2=CC=C(C=C2)Cl)O)C=CC(=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a stirred solution of 2,4-dichlorobenzaldehyde (286 mmol) in diethyl ether (500 mL) was added 4-chlorophenylmagnesium bromide (1.0 M in diethyl ether, 286 mmol) dropwise at 0° C. over a period of 1 hour. The reaction was allowed to warm to ambient temperature, and stirred for 3 h. The reaction mixture was quenched w... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br-.Mg | C(C)OCC | null | 3 | Clc1cc[c]([Mg][Br])cc1.O=Cc1ccc(Cl)cc1Cl>C(C)OCC>OC(c1ccc(Cl)cc1)c1ccc(Cl)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a35001a2ca2e4f4a9f08929975dd943e | OC(c1ccc(Cl)cc1)c1ccc(Cl)cc1Cl.OC1CN(C(c2ccccc2)c2ccccc2)C1>>Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2Cl)cc1 | ClC1=C(C(C2=CC=C(C=C2)Cl)O)C=CC(=C1)Cl.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)O>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl | O[CH:6]([c:5]1[cH:4][cH:3][c:2]([Cl:1])[cH:34][cH:33]1)[c:25]1[cH:26][cH:27][c:28]([Cl:29])[cH:30][c:31]1[Cl:32].[OH:7][CH:8]1[CH2:9][N:10]([CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([O:7][CH:8]2[CH2:9][N:10]([CH:11]([c... | OC(c1ccc(Cl)cc1)c1ccc(Cl)cc1Cl.OC1CN(C(c2ccccc2)c2ccccc2)C1 | Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2Cl)cc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | ab0e50beb55eda2f96023d5223aabdb4b40bd8f8bf0e966622b4956651468e37 | 9f2e9a9638dcdcebec028641448b041be5c5e7e2c9998af6fd20f76a5512fb01 | c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2)cc1 | O-[CH;D3;+0:1](-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7].[OH;D1;+0:8]-[C:9]1-[C:10]-[#7:11]-[C:12]-1>>[c:3]:[c:2](-[CH;D3;+0:1](-[O;H0;D2;+0:8]-[C:9]1-[C:10]-[#7:11]-[C:12]-1)-[c:5](:[c:6]):[c:7]):[c:4] | 50 | [{"value": 50.0, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.7, "product": "C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,4,4′-trichlorobenzhydrol (2) (174 mmol), p-toluenesulfonic acid (174 mmol) and 1-benzhydryl-3-azetidinol (1) (87 mmol) in toluene (700 mL) was heated at reflux under Dean-Stark conditions for 30 minutes. The solution was cooled, washed with sodium hydrogen carbonate (saturated aqueous solution, 700 mL),... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol | Ether | null | null | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | OC(c1ccc(Cl)cc1)c1ccc(Cl)cc1Cl.OC1CN(C(c2ccccc2)c2ccccc2)C1>C1(=CC=CC=C1)C>Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-106c1a67238641f0957055dcc6230eb1 | CC(Cl)OC(=O)Cl.Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2Cl)cc1>>CCOC(C)=O.CO.[NH4+].[OH-] | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl.ClC(C)OC(=O)Cl>>C(C)(=O)OCC.CO.[OH-].[NH4+] | Cl[CH:2]([CH3:1])[O:3][C:4](Cl)=[O:6].Clc1ccc(C(c2ccc(Cl)[cH:5]c2)[O:8][CH:7]2C[N:9](C(c3ccccc3)c3ccccc3)C2)c(Cl)c1>>[CH3:1][CH2:2][O:3][C:4]([CH3:5])=[O:6].[CH3:7][OH:8].[NH4+:9].[OH-:10] | CC(Cl)OC(=O)Cl.Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2Cl)cc1 | CCOC(C)=O.CO.[NH4+].[OH-] | null | null | ClCCl | C-C Coupling | OtherReaction | 9be8b20ddcc71eed826554deb2ac2944fe1d45bf22daecd0f9be5047555d454d | 380b2645de96fe544527f7fae1f717a259193c362739b059c491bc04b8da11a4 | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[CH;D3;+0:4](-Cl)-[C;D1;H3:5].Cl-c1:[cH;D2;+0:6]:c:c(-C(-[O;H0;D2;+0:7]-[CH;D3;+0:8]2-C-[N;H0;D3;+0:9](-C(-c3:c:c:c:c:c:3)-c3:c:c:c:c:c:3)-C-2)-c2:c:c:c(-Cl):c:c:2-Cl):c:c:1>>[C;D1;H3:5]-[CH2;D2;+0:4]-[#8:3]-[C;H0;D3;+0:1](-[CH3;D1;+0:6])=[O;D1;H0:2].[CH3;D1;+0:8]-[OH;D1;+0:7].[NH... | 60 | [{"value": 60.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred solution of 1-benzhydryl-3-(2,4,4′-trichlorobenzhydryloxy)azetidine (3) (39 mmol) in dichloromethane (400 mL) was added 1-chloroethylchloroformate (98 mmol) dropwise at 0° C. and the reaction mixture stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, then dissolved in me... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide.Aromatic halide.Aromatic halide.Secondary halide.Ether.Ether.Tertiary amine | Ester.Methanol | c1ccccc1.c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1 | null | null | HCl | ClCCl | null | 8 | CC(Cl)OC(=O)Cl.Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2Cl)cc1>ClCCl>CCOC(C)=O.CO.[NH4+].[OH-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dadc29b445ee4248bebd3f3b717da235 | CC(C)(C)N=C=O.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2Cl)cc1>>CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1 | ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC(=C1)Cl.C(C)(C)(C)N=C=O.C(C)N(CC)CC>>ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC(=C1)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[N:5]=[C:6]=[O:7].[NH:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]2)[c:20]2[cH:21][cH:22][c:23]([Cl:24])[cH:25][c:26]2[Cl:27])[CH2:28]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([O:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([Cl... | CC(C)(C)N=C=O.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2Cl)cc1 | CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1 | null | null | ClCCl | Acylation | Urea synthesis via isocyanate and secondary amine | 2ebf7ef23b6849ca70c2e2956b56c445033b5017b9bc69ed1f5a167729b0c3a2 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[O;D1;H0:7].[C:8]1-[C:9]-[NH;D2;+0:10]-[C:11]-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:11]-1 | 33 | [{"value": 33.0, "product": "ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC(=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.0, "product": "ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CN(C2)C(=O)NC(C)(C)C)C=CC(=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a stirred solution of 3-(2,4,4′-trichlorobenzhydryloxy)azetidine (4) (3 mmol) in dichloromethane (10 mL) was added tert-butyl isocyanate (3 mmol) and triethylamine (catalytic amount) and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was eluted through a pre-wetted (CH2Cl2) SC... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | ClCCl | null | 3 | CC(C)(C)N=C=O.Clc1ccc(C(OC2CNC2)c2ccc(Cl)cc2Cl)cc1>ClCCl>CC(C)(C)NC(=O)N1CC(OC(c2ccc(Cl)cc2)c2ccc(Cl)cc2Cl)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a11525eb48d4e06a5e6cf67c09aa1bb | O=C(c1ccc(Cl)cc1)c1ccccc1Cl>>OC(c1ccc(Cl)cc1)c1ccccc1Cl | ClC1=C(C(=O)C2=CC=C(C=C2)Cl)C=CC=C1.[BH4-].[Na+]>>ClC1=C(C(C2=CC=C(C=C2)Cl)O)C=CC=C1 | [O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[Cl:16]>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][cH:9]1)[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[Cl:16] | O=C(c1ccc(Cl)cc1)c1ccccc1Cl | OC(c1ccc(Cl)cc1)c1ccccc1Cl | null | null | CO | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(Cc2ccccc2)cc1 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8] | 78 | [{"value": 78.0, "product": "ClC1=C(C(C2=CC=C(C=C2)Cl)O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.9, "product": "ClC1=C(C(C2=CC=C(C=C2)Cl)O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a stirred solution of 2,4′-dichlorobenzophenone (239 mmol) in methanol (400 mL) was added sodium borohydride (119 mmol) portionwise at 0° C. Reaction mixture was warmed to room temperature and stirred for 1 hour, then quenched with water and the methanol was removed under reduced pressure. The residue was diluted wi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1.c1ccccc1 | null | CO | null | 1 | O=C(c1ccc(Cl)cc1)c1ccccc1Cl>CO>OC(c1ccc(Cl)cc1)c1ccccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-19df17d08103449b8e050be2f961799e | OC(c1ccc(Cl)cc1)c1ccccc1Cl.OC1CN(C(c2ccccc2)c2ccccc2)C1>>Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2Cl)cc1 | ClC1=C(C(C2=CC=C(C=C2)Cl)O)C=CC=C1.C1(=CC=C(C=C1)S(=O)(=O)O)C.C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)O>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)Cl)C1=CC=C(C=C1)Cl | [Cl:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([OH:7])[c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]2[Cl:31])[cH:32][cH:33]1.O[CH:8]1[CH2:9][N:10]([CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([O:7][CH:8]2[CH2:9][N:10]([CH:11]([c:12]3[cH... | OC(c1ccc(Cl)cc1)c1ccccc1Cl.OC1CN(C(c2ccccc2)c2ccccc2)C1 | Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2Cl)cc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 93ff1e6bb4175b74747d15c5fea2c034a8b0a5670aa7d98aa342e77dee3c140b | 9f2e9a9638dcdcebec028641448b041be5c5e7e2c9998af6fd20f76a5512fb01 | c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[#7:3](-[C:4])-[C:5]-1.[OH;D1;+0:6]-[C:7](-[c:8])-[c:9]>>[C:4]-[#7:3]1-[C:2]-[CH;D3;+0:1](-[O;H0;D2;+0:6]-[C:7](-[c:8])-[c:9])-[C:5]-1 | null | [] | null | null | null | null | A solution of 2,4′-dichlorobenzhydrol (7) (178 mmol), p-toluenesulphonic acid (198 mmol) and 1-benzhydryl-3-azetidinol (1) (99 mmol) in toluene (500 mL) was heated at reflux in a Dean-Stark apparatus for 40 minutes. The solution was cooled, washed with sodium hydrogen carbonate (saturated aqueous solution, 700 mL), dri... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol | Ether | C1C[NH]C1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | OC(c1ccc(Cl)cc1)c1ccccc1Cl.OC1CN(C(c2ccccc2)c2ccccc2)C1>C1(=CC=CC=C1)C>Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ab1297454164a85bff1887573bddc30 | CC(Cl)OC(=O)Cl.Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2Cl)cc1>>Cl.Clc1ccc(C(OC2CNC2)c2ccccc2Cl)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=CC=C1)Cl)C1=CC=C(C=C1)Cl.ClC(C)OC(=O)Cl>>Cl.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1 | CC(Cl)OC(=O)[Cl:1].c1ccc(C(c2ccccc2)[N:11]2[CH2:10][CH:9]([O:8][CH:7]([c:6]3[cH:5][cH:4][c:3]([Cl:2])[cH:21][cH:20]3)[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[Cl:19])[CH2:12]2)cc1>>[ClH:1].[Cl:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([O:8][CH:9]2[CH2:10][NH:11][CH2:12]2)[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[Cl:19])[cH:20... | CC(Cl)OC(=O)Cl.Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2Cl)cc1 | Cl.Clc1ccc(C(OC2CNC2)c2ccccc2Cl)cc1 | null | null | ClCCl | Miscellaneous | OtherReaction | 89a5abfed04083d8a577adf1e6b601d847582832e04d2c8e6d772c9562443319 | 8680972761abf0bd12e62e23250487041204d99e9f76a29275e470fb95a71c86 | c1ccc(C(OC2CNC2)c2ccccc2)cc1 | C-C(-Cl)-O-C(=O)-[Cl;H0;D1;+0:1].[C:2]1-[C:3]-[C:4]-[N;H0;D3;+0:5]-1-C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:2]1-[C:3]-[C:4]-[NH;D2;+0:5]-1.[ClH;D0;+0:1] | 154.2 | [{"value": 77.0, "product": "Cl.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 154.2, "product": "Cl.ClC1=C(C(C2=CC=C(C=C2)Cl)OC2CNC2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred solution of 1-benzhydryl-3-(2,4′-dichlorobenzhydryloxy)azetidine (8) (38 mmol) in dichloromethane (400 mL) was added 1-chloroethylchloroformate (94 mmol) dropwise at 0° C. and the reaction mixture stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, then dissolved in metha... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary halide.Ether.Tertiary amine | Secondary amine | c1ccccc1.c1ccccc1.C1C[NH]C1 | C1CNC1 | c1ccccc1.C1CNC1.c1ccccc1 | HCl | ClCCl | null | 8 | CC(Cl)OC(=O)Cl.Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2Cl)cc1>ClCCl>Cl.Clc1ccc(C(OC2CNC2)c2ccccc2Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f45a528f3874963b37c93c375f2c487 | Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2Cl)cc1.OC1CN(C(c2ccccc2)c2ccccc2)C1>>Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2)cc1 | C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)O.ClC1=CC=C(C(C2=CC=C(C=C2)Cl)O)C=C1.C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=C(C=C(C=C1)Cl)Cl)C1=CC=C(C=C1)Cl>>C(C1=CC=CC=C1)(C1=CC=CC=C1)N1CC(C1)OC(C1=CC=C(C=C1)Cl)C1=CC=C(C=C1)Cl | Cl[c:31]1[c:25]([CH:6](OC2CN(C(c3ccccc3)c3ccccc3)C2)[c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:33][cH:32]2)[cH:26][cH:27][c:28]([Cl:29])[cH:30]1.[OH:7][CH:8]1[CH2:9][N:10]([CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH2:24]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([O:7][CH:8]2... | Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2Cl)cc1.OC1CN(C(c2ccccc2)c2ccccc2)C1 | Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d7f6f65d4bab12ad181b21ef5da5fd34bcec47ee618bc6cdb85803c6fe4a264f | 2bb09e0396e5cf4af4f8ab6d711e1aa6aaa68c6b2482b2b3ce2e97ed591ad47e | c1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccccc2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[CH;D3;+0:5](-O-C1-C-N(-C(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2)-C-1)-[c:6](:[c:7]):[c:8]):[c:9].[OH;D1;+0:10]-[C:11]1-[C:12]-[#7:13]-[C:14]-1>>[c:9]:[c:4](-[CH;D3;+0:5](-[O;H0;D2;+0:10]-[C:11]1-[C:12]-[#7:13]-[C:14]-1)-[c:6](:[c:7]):[c:8]):[cH;D2;+0:1]:[c:2]:[c:3] | null | [] | null | null | null | null | This material was prepared from 1-benzhydryl-3-azetidinol (1) (45.0 mmol) and 4,4′-dichlorobenzhydrol (90.0 mmol) using the procedure described for compound (3) (8.6 g, 40%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Secondary alcohol.Tertiary amine | Ether | c1ccccc1.C1CNC1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2Cl)cc1.OC1CN(C(c2ccccc2)c2ccccc2)C1>>Clc1ccc(C(OC2CN(C(c3ccccc3)c3ccccc3)C2)c2ccc(Cl)cc2)cc1 |
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