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-6d8bca8ea5284e3f8ed438df0067ff81 | Cn1ccnc1.O=C(c1ccc(F)cc1)c1ccc2nc(Cl)nc(-c3cccc(Cl)c3)c2c1>>Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2nc(Cl)nc(-c3cccc(Cl)c3)c2c1 | Cl[Si](CC)(CC)CC.ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(=O)C1=CC=C(C=C1)F.[Li]CCCC.CCCCCC.[Li]CCCC.CCCCCC.CN1C=NC=C1>>ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)F | [CH3:1][n:2]1[cH:3][n:4][cH:5][cH:6]1.[C:7](=[O:8])([c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1)[c:16]1[cH:17][cH:18][c:19]2[n:20][c:21]([Cl:22])[n:23][c:24](-[c:25]3[cH:26][cH:27][cH:28][c:29]([Cl:30])[cH:31]3)[c:32]2[cH:33]1>>[CH3:1][n:2]1[cH:3][n:4][cH:5][c:6]1[C:7]([OH:8])([c:9]1[cH:10][cH:11][c:12]([F:13])[c... | Cn1ccnc1.O=C(c1ccc(F)cc1)c1ccc2nc(Cl)nc(-c3cccc(Cl)c3)c2c1 | Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2nc(Cl)nc(-c3cccc(Cl)c3)c2c1 | null | null | O.CCOC(=O)C.C1CCOC1 | C-C Coupling | OtherReaction | 3433c90914e9b30e9a7c8b7d908911f5bba34cfc8cc88706413738357bc5fa4d | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1ccc(-c2ncnc3ccc(C(c4ccccc4)c4cnc[nH]4)cc23)cc1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[cH;D2;+0:6]:1.[O;H0;D1;+0:7]=[C;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]>>[C;D1;H3:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[c;H0;D3;+0:6]:1-[C;H0;D4;+0:8](-[OH;D1;+0:7])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14] | 0.8 | [{"value": 0.8, "product": "ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | 15 | MINUTE | BuLi 1.6M in hexane (46.5 ml, 0.0744 mol) was added dropwise at −70° C. to a mixture of 1-methyl-1H-imidazole (0.0744 mol) in THF (70 ml) under N2 flow. Chlorotriethyl-silane (0.0765 mol) was added dropwise at −70° C. The mixture was stirred at −70° C. for 15 minutes. BuLi 1.6M in hexane (41 ml, 0.0659 mol) was added d... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1c[nH]cn1 | c1cnc[nH]1 | c1cnc[nH]1.c1ccccc1.c1ccc2ncncc2c1.c1ccccc1 | null | O.CCOC(=O)C.C1CCOC1 | -70 | 0.25 | Cn1ccnc1.O=C(c1ccc(F)cc1)c1ccc2nc(Cl)nc(-c3cccc(Cl)c3)c2c1>O.CCOC(=O)C.C1CCOC1>Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2nc(Cl)nc(-c3cccc(Cl)c3)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eecfee5fb078407e937e0238498d097c | Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2nc(Cl)nc(-c3cccc(Cl)c3)c2c1.[N-]=[N+]=[N-]>>Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2c(c1)c(-c1cccc(Cl)c1)nc1nnnn12 | ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)F.[N-]=[N+]=[N-].[Na+]>>ClC=1C=C(C=CC1)C1=NC=2N(C3=CC=C(C=C13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)F)N=NN2 | Cl[c:31]1[n:30][c:22](-[c:23]2[cH:24][cH:25][cH:26][c:27]([Cl:28])[cH:29]2)[c:20]2[c:19]([cH:18][cH:17][c:16]([C:7]([c:6]3[n:2]([CH3:1])[cH:3][n:4][cH:5]3)([OH:8])[c:9]3[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]3)[cH:21]2)[n:35]1.[N-:32]=[N+:34]=[N-:33]>>[CH3:1][n:2]1[cH:3][n:4][cH:5][c:6]1[C:7]([OH:8])([c:9]1[cH:10][c... | Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2nc(Cl)nc(-c3cccc(Cl)c3)c2c1.[N-]=[N+]=[N-] | Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2c(c1)c(-c1cccc(Cl)c1)nc1nnnn12 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 4e0cb3e54897e660c5677e719a9c21ad2978ab17efb16dd9052e527979ac46a1 | 155f764f095c8454a4ad08aaa42f1abcb15d5bc1d4f122e4bcc624dd834362f2 | c1ccc(-c2nc3nnnn3c3ccc(C(c4ccccc4)c4cnc[nH]4)cc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[c:6]):[n;H0;D2;+0:7]:1.[N-;H0;D1:8]=[N+;H0;D2:9]=[N-;H0;D1:10]>>[c:6]:[c:5]1:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]2:[n;H0;D2;+0:8]:[n;H0;D2;+0:10]:[n;H0;D2;+0:9]:[n;H0;D3;+0:7]:1:2 | 58 | [{"value": 58.0, "product": "ClC=1C=C(C=CC1)C1=NC=2N(C3=CC=C(C=C13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)F)N=NN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.6, "product": "ClC=1C=C(C=CC1)C1=NC=2N(C3=CC=C(C=C13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)F)N=NN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 2 | HOUR | A mixture of intermediate 7 (0.0125 mol) and sodium azide (0.038 mol) in DMF (60 ml) was stirred at 90° C. for 2 hours, then brought to room temperature, poured out into ice water and stirred. The precipitate was filtered, washed with water, taken up in DCM, filtered, washed with diethyl ether and dried under a vacuo, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2ncncc2c1 | c1ccc2c(c1)cnc1nnnn12 | c1cnc[nH]1.c1ccccc1.c1ccccc1.c1ccc2c(c1)cnc1nnnn12 | Other | CN(C)C=O | 90 | 2 | Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2nc(Cl)nc(-c3cccc(Cl)c3)c2c1.[N-]=[N+]=[N-]>CN(C)C=O>Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2c(c1)c(-c1cccc(Cl)c1)nc1nnnn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-97c34b6fceb2400cb6294c78a72f8bf3 | Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2c(c1)c(-c1cccc(Cl)c1)nc1nnnn12>>Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2c(c1)C(c1cccc(Cl)c1)Nc1nnnn1-2 | C(Cl)Cl.[B-].[Na+].ClC=1C=C(C=CC1)C1=NC=2N(C3=CC=C(C=C13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)F)N=NN2>>ClC=1C=C(C=CC1)C1NC=2N(C3=CC=C(C=C13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)F)N=NN2 | [CH3:1][n:2]1[cH:3][n:4][cH:5][c:6]1[C:7]([OH:8])([c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1)[c:16]1[cH:17][cH:18][c:19]2[c:20]([cH:21]1)[c:22](-[c:23]1[cH:24][cH:25][cH:26][c:27]([Cl:28])[cH:29]1)[n:30][c:31]1[n:32][n:33][n:34][n:35]21>>[CH3:1][n:2]1[cH:3][n:4][cH:5][c:6]1[C:7]([OH:8])([c:9]1[cH:10][cH:11][c:12... | Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2c(c1)c(-c1cccc(Cl)c1)nc1nnnn12 | Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2c(c1)C(c1cccc(Cl)c1)Nc1nnnn1-2 | null | null | CO | Reduction | OtherReaction | 68fa0e5ecb7fd022bbef2c0545f4aab67cdefa951d7696965b374d746a3ba330 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | c1ccc(C2Nc3nnnn3-c3ccc(C(c4ccccc4)c4cnc[nH]4)cc32)cc1 | [c:1]:[c:2]:[c;H0;D3;+0:3]1:[c:4](:[c:5]):[c;H0;D3;+0:6](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[n;H0;D2;+0:12]:[c:13]2:[#7;a:14]:[#7;a:15]:[#7;a:16]:[n;H0;D3;+0:17]:2:1>>[c:1]:[c:2]:[c;H0;D3;+0:3]1:[c:4](:[c:5])-[CH;D3;+0:6](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11])-[NH;D2;+0:12]-[c:13]2:[#7;a:14]:[#7;a:15]:[... | 21.5 | [{"value": 21.0, "product": "ClC=1C=C(C=CC1)C1NC=2N(C3=CC=C(C=C13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)F)N=NN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.5, "product": "ClC=1C=C(C=CC1)C1NC=2N(C3=CC=C(C=C13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)F)N=NN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Sodium hydroborate (0.001 mol) was added portionwise at room temperature to a mixture of intermediate 8 (0.001 mol) in methanol (5 ml). The mixture was stirred at room temperature for 2 hours and poured out into ice water. DCM was added. The organic layer was washed with water, separated, dried (MgSO4), filtered and th... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccc2c(c1)cnc1nnnn12 | c1ccc2c(c1)CNc1nnnn12 | c1cnc[nH]1.c1ccccc1.c1ccccc1.c1ccc2c(c1)CNc1nnnn12 | null | CO | null | 2 | Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2c(c1)c(-c1cccc(Cl)c1)nc1nnnn12>CO>Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2c(c1)C(c1cccc(Cl)c1)Nc1nnnn1-2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7bfe84fd85094276ad6be475386f2c07 | COc1ccc(C(=O)N(C)OC)cc1.Clc1cccc(-c2onc3ccc(Br)cc23)c1>>COc1ccc(C(=O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1 | [Li]CCCC.BrC=1C=CC=2C(=C(ON2)C2=CC(=CC=C2)Cl)C1.CON(C(C1=CC=C(C=C1)OC)=O)C>>ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(=O)C2=CC=C(C=C2)OC | CON(C)[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:26][cH:25]1)=[O:8].Br[c:9]1[cH:10][cH:11][c:12]2[n:13][o:14][c:15](-[c:16]3[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]3)[c:23]2[cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]3[n:13][o:14][c:15](-[c:16]4[cH:17][cH:18][cH:19][c:20]... | COc1ccc(C(=O)N(C)OC)cc1.Clc1cccc(-c2onc3ccc(Br)cc23)c1 | COc1ccc(C(=O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | ed7d0f62acc084fc2d1c32686cb3eb636bc801b108aa5e5891b600d5eadc5405 | 7d9aa59f8ecc532475d910f9ab122332ecbb7f9444a37371b7c1bac80798d342 | O=C(c1ccccc1)c1ccc2noc(-c3ccccc3)c2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[#8;a:6]:[c:7]:[c:8]:2:[c:9]:1.C-O-N(-C)-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12](:[c:13]):[c:14]>>[O;D1;H0:11]=[C;H0;D3;+0:10](-[c:12](:[c:13]):[c:14])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[#8;a:6]:[c:7]:[c:8]:2:[c:9]:1 | 41 | [{"value": 41.0, "product": "ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(=O)C2=CC=C(C=C2)OC", "details": "PERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | 10 | MINUTE | 5-bromo-3-(3-chlorophenyl)-2,1-benzisoxazole (0.13 m) was added at −70° C. to THF (300 ml) under N2 flow. A solution of BuLi (0.143 mol) was added dropwise. The mixture was stirred at −70° C. for 10 minutes. A solution of N,4-dimethoxy-N-methylbenzamide (0.117 mol) in THF (100 ml) was added dropwise at −70° C. The mixt... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Ketone | c1ccc2nocc2c1 | c1ccc2nocc2c1 | c1ccccc1.c1ccc2nocc2c1.c1ccccc1 | HBr | C1CCOC1 | -70 | 0.166667 | COc1ccc(C(=O)N(C)OC)cc1.Clc1cccc(-c2onc3ccc(Br)cc23)c1>C1CCOC1>COc1ccc(C(=O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-caaed9f827414c17971404255f2117a8 | COc1ccc(C(=O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1>>COc1ccc(C(=O)c2ccc(N)c(C(=O)c3cccc(Cl)c3)c2)cc1 | ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(=O)C2=CC=C(C=C2)OC.C1CCOC1>>NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)OC)=O)C(=O)C1=CC(=CC=C1)Cl | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]3[n:13][o:16][c:15](-[c:17]4[cH:18][cH:19][cH:20][c:21]([Cl:22])[cH:23]4)[c:14]3[cH:24]2)[cH:25][cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([NH2:13])[c:14]([C:15](=[O:16])[c:17]3[cH:18][cH:19][cH:20][c:2... | COc1ccc(C(=O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1 | COc1ccc(C(=O)c2ccc(N)c(C(=O)c3cccc(Cl)c3)c2)cc1 | null | null | O | Miscellaneous | OtherReaction | 63dfc430e67d3a7ada3c7e8f6e094ee16a92b905651085a196381d3119990ee1 | 2e99338cc955e46b2c0e811178d7128dca9a68ef9fbb467724eba7220efe12b0 | O=C(c1ccccc1)c1cccc(C(=O)c2ccccc2)c1 | [c:1]:[c:2]1:[n;H0;D2;+0:3]:[o;H0;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:11]:1:[c:12]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:11](-[C;H0;D3;+0:5](=[O;H0;D1;+0:4])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:12] | 104.6 | [{"value": 104.6, "product": "NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)OC)=O)C(=O)C1=CC(=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Intermediate 10 (0.0536 mol) was added at room temperature to THF (200 ml). TiCl3 15% in water (120 ml) was added dropwise at room temperature. The mixture was stirred at room temperature for 3 hours, poured out into ice water and extracted with DCM. The organic layer was separated, washed with K2CO3 10% then with wate... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone.Primary amine | c1ccc2nocc2c1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | null | O | null | 3 | COc1ccc(C(=O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1>O>COc1ccc(C(=O)c2ccc(N)c(C(=O)c3cccc(Cl)c3)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cc951cb177d4449cbb7983bb42eb8ee5 | COc1ccc(C(=O)c2ccc(N)c(C(=O)c3cccc(Cl)c3)c2)cc1.O=C(Cl)C(Cl)(Cl)Cl>>COc1ccc(C(=O)c2ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c3cccc(Cl)c3)c2)cc1 | ClC(C(=O)Cl)(Cl)Cl.NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)OC)=O)C(=O)C1=CC(=CC=C1)Cl.C(C)N(CC)CC>>ClC(C(=O)NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)OC)=O)C(C1=CC(=CC=C1)Cl)=O)(Cl)Cl | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([NH2:13])[c:20]([C:21](=[O:22])[c:23]3[cH:24][cH:25][cH:26][c:27]([Cl:28])[cH:29]3)[cH:30]2)[cH:31][cH:32]1.Cl[C:14](=[O:15])[C:16]([Cl:17])([Cl:18])[Cl:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([NH:13][C:... | COc1ccc(C(=O)c2ccc(N)c(C(=O)c3cccc(Cl)c3)c2)cc1.O=C(Cl)C(Cl)(Cl)Cl | COc1ccc(C(=O)c2ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c3cccc(Cl)c3)c2)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(c1ccccc1)c1cccc(C(=O)c2ccccc2)c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])(-[Cl;D1;H0:5])-[Cl;D1;H0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]-[C:11]=[O;D1;H0:12]>>[Cl;D1;H0:4]-[C:3](-[Cl;D1;H0:5])(-[Cl;D1;H0:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]-[C:11]=[O;D1;H0:12] | 100 | [{"value": 100.0, "product": "ClC(C(=O)NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)OC)=O)C(C1=CC(=CC=C1)Cl)=O)(Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 30 | MINUTE | A mixture of intermediate 11 (0.0536 mol) in DCM (200 ml) was cooled to 5° C. under N2 flow. A solution of trichloro-acetylchloride (0.0643 mol) was added dropwise at 5° C. The mixture was stirred at 5° C. for 30 minutes. A solution of triethylamine (0.0643 mol) was added dropwise at 5° C. The mixture was stirred at 5°... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | 5 | 0.5 | COc1ccc(C(=O)c2ccc(N)c(C(=O)c3cccc(Cl)c3)c2)cc1.O=C(Cl)C(Cl)(Cl)Cl>C(Cl)Cl>COc1ccc(C(=O)c2ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c3cccc(Cl)c3)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0577cb35c37947539e65a4f808a902ca | COc1ccc(C(=O)c2ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c3cccc(Cl)c3)c2)cc1.[NH4+]>>COc1ccc(C(=O)c2ccc3[nH]c(=O)nc(-c4cccc(Cl)c4)c3c2)cc1 | [NH4+].C(C)(=O)[O-].ClC(C(=O)NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)OC)=O)C(C1=CC(=CC=C1)Cl)=O)(Cl)Cl>>ClC=1C=C(C=CC1)C1=NC(NC2=CC=C(C=C12)C(C1=CC=C(C=C1)OC)=O)=O | O=[C:17]([c:18]1[cH:19][cH:20][cH:21][c:22]([Cl:23])[cH:24]1)[c:25]1[c:12]([NH:13][C:14](C(Cl)(Cl)Cl)=[O:15])[cH:11][cH:10][c:9]([C:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28][cH:27]2)=[O:8])[cH:26]1.[NH4+:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]3[nH:13][c:14](=[O:15])[n:16][... | COc1ccc(C(=O)c2ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c3cccc(Cl)c3)c2)cc1.[NH4+] | COc1ccc(C(=O)c2ccc3[nH]c(=O)nc(-c4cccc(Cl)c4)c3c2)cc1 | null | null | CS(=O)C | Aromatic Heterocycle Formation | OtherReaction | 34356251393ced07649e3f2d79584418a4a8dc983e24c794ec9fd18e790ecc31 | 1620ff2b4fcf2514dc5381b8c0e77d605f9d7258e5a6b5dfb277498e8a5ebb1a | O=C(c1ccccc1)c1ccc2[nH]c(=O)nc(-c3ccccc3)c2c1 | Cl-C(-Cl)(-Cl)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6](-[C;H0;D3;+0:7](=O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:13].[NH4+;D0:14]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[n;H0;D2;+0:14]:[c;H0;D3;+0:7](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:6](:[c:13]):[c:4](:[c:5]):[nH;D2;+0:3]:1 | 77.3 | [{"value": 77.0, "product": "ClC=1C=C(C=CC1)C1=NC(NC2=CC=C(C=C12)C(C1=CC=C(C=C1)OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.3, "product": "ClC=1C=C(C=CC1)C1=NC(NC2=CC=C(C=C12)C(C1=CC=C(C=C1)OC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | Acetic acid, ammonium salt (0.107 mol) was added at room temperature to a mixture of intermediate 12 (0.0536 mol) in DMSO (250 ml). The mixture was stirred at 60° C. for 4 hours then brought to room temperature, poured out into ice water and stirred. The precipitate was filtered, washed with water and taken up in warm ... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ketone.Secondary amide | null | c1ccccc1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1.c1ccccc1 | HCl | CS(=O)C | 60 | 4 | COc1ccc(C(=O)c2ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c3cccc(Cl)c3)c2)cc1.[NH4+]>CS(=O)C>COc1ccc(C(=O)c2ccc3[nH]c(=O)nc(-c4cccc(Cl)c4)c3c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e9c107f6ada94c5c89435144078d6159 | COc1ccc(C(=O)c2ccc3[nH]c(=O)nc(-c4cccc(Cl)c4)c3c2)cc1.O=P(Cl)(Cl)Cl>>COc1ccc(C(=O)c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)cc1 | ClC=1C=C(C=CC1)C1=NC(NC2=CC=C(C=C12)C(C1=CC=C(C=C1)OC)=O)=O.P(=O)(Cl)(Cl)Cl>>ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(=O)C1=CC=C(C=C1)OC | O=[c:14]1[nH:13][c:12]2[cH:11][cH:10][c:9]([C:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:28][cH:27]3)=[O:8])[cH:26][c:25]2[c:17](-[c:18]2[cH:19][cH:20][cH:21][c:22]([Cl:23])[cH:24]2)[n:16]1.O=P(Cl)(Cl)[Cl:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]3[n:13][c:14]([Cl:15])[n:16][c:17]... | COc1ccc(C(=O)c2ccc3[nH]c(=O)nc(-c4cccc(Cl)c4)c3c2)cc1.O=P(Cl)(Cl)Cl | COc1ccc(C(=O)c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)cc1 | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C(c1ccccc1)c1ccc2ncnc(-c3ccccc3)c2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6](:[c:7]):[nH;D2;+0:8]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6](:[c:7]):[n;H0;D2;+0:8]:1 | 87 | [{"value": 87.0, "product": "ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(=O)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 3 | HOUR | Intermediate 13 (0.0432 mol) was added at room temperature to phosphoryl chloride (150 ml). The mixture was stirred at 100° C. for 3 hours then brought to room temperature. The solvent was evaporated till dryness. The residue was taken up in DCM. The solvent was evaporated. The residue was taken up in DCM. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1.c1ccccc1 | HCl | null | 100 | 3 | COc1ccc(C(=O)c2ccc3[nH]c(=O)nc(-c4cccc(Cl)c4)c3c2)cc1.O=P(Cl)(Cl)Cl>>COc1ccc(C(=O)c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a4fac1bba674e4796294de9779081be | COc1ccc(C(=O)c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)cc1.Cn1ccnc1>>COc1ccc(C(O)(c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)c2cncn2C)cc1 | [Li]CCCC.CN1C=NC=C1.ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(=O)C1=CC=C(C=C1)OC.Cl[Si](CC)(CC)CC>>ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]3[n:13][c:14]([Cl:15])[n:16][c:17](-[c:18]4[cH:19][cH:20][cH:21][c:22]([Cl:23])[cH:24]4)[c:25]3[cH:26]2)[cH:33][cH:34]1.[cH:27]1[cH:28][n:29][cH:30][n:31]1[CH3:32]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([OH:8])([c:9]2[cH:10][cH:11][c:12]3[n:... | COc1ccc(C(=O)c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)cc1.Cn1ccnc1 | COc1ccc(C(O)(c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)c2cncn2C)cc1 | null | null | O.CCOC(=O)C.C1CCOC1 | C-C Coupling | OtherReaction | 05395e7d28d1a7c287cdf9872044b38b254b469c1c451b45b37d37651dd6bc83 | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1ccc(-c2ncnc3ccc(C(c4ccccc4)c4cnc[nH]4)cc23)cc1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[cH;D2;+0:6]:1.[O;H0;D1;+0:7]=[C;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]>>[C;D1;H3:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[c;H0;D3;+0:6]:1-[C;H0;D4;+0:8](-[OH;D1;+0:7])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14] | 59 | [{"value": 59.0, "product": "ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.9, "product": "ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | nBuLi (0.0665 mol) was added dropwise at −70° C. to a solution of 1-methyl-1H-imidazole (0.0665 mol) in THF (60 ml) under N2 flow. The mixture was stirred for 15 minutes. Chlorotriethyl-silane (0.0684 mol) was added dropwise. The mixture was stirred for 15 minutes. nBuli (0.059 mol) was added dropwise. The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccc2ncncc2c1.c1ccccc1.c1c[nH]cn1 | null | O.CCOC(=O)C.C1CCOC1 | null | 0.25 | COc1ccc(C(=O)c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)cc1.Cn1ccnc1>O.CCOC(=O)C.C1CCOC1>COc1ccc(C(O)(c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)c2cncn2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3174410cc7aa4d319705df78235927e0 | COc1ccc(C(O)(c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)c2cncn2C)cc1.[N-]=[N+]=[N-]>>COc1ccc(C(O)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1 | ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)OC.[N-]=[N+]=[N-].[Na+]>>ClC=1C=C(C=CC1)C1=NC=2N(C3=CC=C(C=C13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)OC)N=NN2 | Cl[c:24]1[n:23][c:15](-[c:16]2[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]2)[c:13]2[c:12]([cH:11][cH:10][c:9]([C:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:36][cH:35]3)([OH:8])[c:29]3[cH:30][n:31][cH:32][n:33]3[CH3:34])[cH:14]2)[n:28]1.[N-:25]=[N+:27]=[N-:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([OH:8])([c:9]2[cH... | COc1ccc(C(O)(c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)c2cncn2C)cc1.[N-]=[N+]=[N-] | COc1ccc(C(O)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 4e0cb3e54897e660c5677e719a9c21ad2978ab17efb16dd9052e527979ac46a1 | 155f764f095c8454a4ad08aaa42f1abcb15d5bc1d4f122e4bcc624dd834362f2 | c1ccc(-c2nc3nnnn3c3ccc(C(c4ccccc4)c4cnc[nH]4)cc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[c:6]):[n;H0;D2;+0:7]:1.[N-;H0;D1:8]=[N+;H0;D2:9]=[N-;H0;D1:10]>>[c:6]:[c:5]1:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]2:[n;H0;D2;+0:8]:[n;H0;D2;+0:10]:[n;H0;D2;+0:9]:[n;H0;D3;+0:7]:1:2 | 80.7 | [{"value": 80.0, "product": "ClC=1C=C(C=CC1)C1=NC=2N(C3=CC=C(C=C13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)OC)N=NN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.7, "product": "ClC=1C=C(C=CC1)C1=NC=2N(C3=CC=C(C=C13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)OC)N=NN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 2 | HOUR | A mixture of intermediate 15 (0.0224 mol) and sodium azide (0.067 mol) in DMF (120 ml) was stirred at 90° C. for 2 hours, brought to room temperature, poured out into ice water and stirred. The precipitate was filtered, washed with water and taken up in DCM. The organic layer was washed with water, separated, dried (Mg... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2ncncc2c1 | c1ccc2c(c1)cnc1nnnn12 | c1ccccc1.c1ccccc1.c1ccc2c(c1)cnc1nnnn12.c1c[nH]cn1 | Other | CN(C)C=O | 90 | 2 | COc1ccc(C(O)(c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)c2cncn2C)cc1.[N-]=[N+]=[N-]>CN(C)C=O>COc1ccc(C(O)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4dfd5f10146d40e5832362af6c04be9c | COc1ccc(C(O)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1>>COc1ccc(C(O)(c2ccc3c(c2)C(c2cccc(Cl)c2)Nc2nnnn2-3)c2cncn2C)cc1 | C(Cl)Cl.[BH4-].[Na+].ClC=1C=C(C=CC1)C1=NC=2N(C3=CC=C(C=C13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)OC)N=NN2>>ClC=1C=C(C=CC1)C1NC=2N(C3=CC=C(C=C13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)OC)N=NN2 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([OH:8])([c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]2)[n:23][c:24]2[n:25][n:26][n:27][n:28]32)[c:29]2[cH:30][n:31][cH:32][n:33]2[CH3:34])[cH:35][cH:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([OH:8])([c:9]2[cH:10][cH:... | COc1ccc(C(O)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1 | COc1ccc(C(O)(c2ccc3c(c2)C(c2cccc(Cl)c2)Nc2nnnn2-3)c2cncn2C)cc1 | null | null | CO | Reduction | OtherReaction | 68fa0e5ecb7fd022bbef2c0545f4aab67cdefa951d7696965b374d746a3ba330 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | c1ccc(C2Nc3nnnn3-c3ccc(C(c4ccccc4)c4cnc[nH]4)cc32)cc1 | [c:1]:[c:2]:[c;H0;D3;+0:3]1:[c:4](:[c:5]):[c;H0;D3;+0:6](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[n;H0;D2;+0:12]:[c:13]2:[#7;a:14]:[#7;a:15]:[#7;a:16]:[n;H0;D3;+0:17]:2:1>>[c:1]:[c:2]:[c;H0;D3;+0:3]1:[c:4](:[c:5])-[CH;D3;+0:6](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11])-[NH;D2;+0:12]-[c:13]2:[#7;a:14]:[#7;a:15]:[... | 67 | [{"value": 67.0, "product": "ClC=1C=C(C=CC1)C1NC=2N(C3=CC=C(C=C13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)OC)N=NN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.7, "product": "ClC=1C=C(C=CC1)C1NC=2N(C3=CC=C(C=C13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)OC)N=NN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | NaBH4 (0.003 mol) was added portionwise at room temperature to a mixture of intermediate 16 (0.003 mol) in methanol (15 ml). The mixture was stirred at room temperature for 2 hours and poured out into ice water. DCM was added. The mixture was extracted with DCM. The organic layer was separated, dried (MgSO4), filtered,... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccc2c(c1)cnc1nnnn12 | c1ccc2c(c1)CNc1nnnn12 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CNc1nnnn12.c1c[nH]cn1 | null | CO | null | 2 | COc1ccc(C(O)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1>CO>COc1ccc(C(O)(c2ccc3c(c2)C(c2cccc(Cl)c2)Nc2nnnn2-3)c2cncn2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da903ade3be946ffa0911b31ee60f241 | Cc1ccc(C=O)cc1.Clc1cccc(-c2onc3ccc(Br)cc23)c1>>Cc1ccc(C(O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1 | BrC=1C=CC=2C(=C(ON2)C2=CC(=CC=C2)Cl)C1.CC1=CC=C(C=O)C=C1.[Li]CCCC.CCCCCC>>ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(O)C2=CC=C(C=C2)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]=[O:7])[cH:24][cH:25]1.Br[c:8]1[cH:9][cH:10][c:11]2[n:12][o:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][c:19]([Cl:20])[cH:21]3)[c:22]2[cH:23]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][cH:10][c:11]3[n:12][o:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][c:19]([Cl:20])[cH:21]4)... | Cc1ccc(C=O)cc1.Clc1cccc(-c2onc3ccc(Br)cc23)c1 | Cc1ccc(C(O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1 | null | null | C1CCOC1 | C-C Coupling | Grignard_alcohol | f822b053a4342903753b2398efb1ef26df143aa50697f50ef6a150fdf12a512a | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(Cc2ccc3noc(-c4ccccc4)c3c2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[c:4]:[#8;a:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1.[O;H0;D1;+0:10]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[OH;D1;+0:10]-[CH;D3;+0:11](-[c:12](:[c:13]):[c:14])-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[c:4]:[#8;a:5]:[#7;a:6]:[c:7]:2:[c:8]:[c:9]:1 | 38.3 | [{"value": 38.3, "product": "ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(O)C2=CC=C(C=C2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.3, "product": "ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(O)C2=CC=C(C=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | 15 | MINUTE | nBuLi 1.6 M in hexane (0.112 mol) was added dropwise at −70° C. under N2 flow to a mixture of 5-bromo-3-(3-chlorophenyl)-2,1-benzisoxazole (0.097 mol) in THF (300 ml). The mixture was stirred at −70° C. for 15 min. A mixture of 4-methylbenzaldehyde (0.112 mol) in THF (100 ml) was added dropwise. The mixture was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccc2nocc2c1 | c1ccc2nocc2c1 | c1ccccc1.c1ccc2nocc2c1.c1ccccc1 | Br- | C1CCOC1 | -70 | 0.25 | Cc1ccc(C=O)cc1.Clc1cccc(-c2onc3ccc(Br)cc23)c1>C1CCOC1>Cc1ccc(C(O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b8c3594ec5a64ca4a578b8f45428384d | Cc1ccc(C(O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1>>Cc1ccc(C(=O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1 | ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(O)C2=CC=C(C=C2)C>>ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(=O)C2=CC=C(C=C2)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][cH:10][c:11]3[n:12][o:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][c:19]([Cl:20])[cH:21]4)[c:22]3[cH:23]2)[cH:24][cH:25]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]3[n:12][o:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][c:19]([Cl:20])[cH:21]4)[c... | Cc1ccc(C(O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1 | Cc1ccc(C(=O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1 | null | O=[Mn]=O | O1CCOCC1 | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(c1ccccc1)c1ccc2noc(-c3ccccc3)c2c1 | [OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8] | 100 | [{"value": 100.0, "product": "ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(=O)C2=CC=C(C=C2)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.0, "product": "ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(=O)C2=CC=C(C=C2)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | A mixture of intermediate 18 (0.071 mol) and MnO2 (0.287 mol) in 1,4-dioxane (250 ml) was stirred at 80° C. for 2 hours, then cooled to room temperature, filtered over celite and washed with DCM. The solvent was evaporated till dryness, yielding 24.7 g (100%) of [3-(3-chlorophenyl)-2,1-benzisoxazol-5-yl](4-methylphenyl... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccc2nocc2c1.c1ccccc1 | null | O=[Mn]=O.O1CCOCC1 | 80 | 2 | Cc1ccc(C(O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1>O=[Mn]=O.O1CCOCC1>Cc1ccc(C(=O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-af8ca250e0d44d028c48e246ff3d4583 | Cc1ccc(C(=O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1>>Cc1ccc(C(=O)c2ccc(N)c(C(=O)c3cccc(Cl)c3)c2)cc1 | ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(=O)C2=CC=C(C=C2)C>>NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)C)=O)C(=O)C1=CC(=CC=C1)Cl | [CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]3[n:12][o:15][c:14](-[c:16]4[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]4)[c:13]3[cH:23]2)[cH:24][cH:25]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([NH2:12])[c:13]([C:14](=[O:15])[c:16]3[cH:17][cH:18][cH:19][c:20]([Cl:21])[... | Cc1ccc(C(=O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1 | Cc1ccc(C(=O)c2ccc(N)c(C(=O)c3cccc(Cl)c3)c2)cc1 | null | null | O.C1CCOC1 | Miscellaneous | OtherReaction | 63dfc430e67d3a7ada3c7e8f6e094ee16a92b905651085a196381d3119990ee1 | 2e99338cc955e46b2c0e811178d7128dca9a68ef9fbb467724eba7220efe12b0 | O=C(c1ccccc1)c1cccc(C(=O)c2ccccc2)c1 | [c:1]:[c:2]1:[n;H0;D2;+0:3]:[o;H0;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:11]:1:[c:12]>>[NH2;D1;+0:3]-[c:2](:[c:1]):[c:11](-[C;H0;D3;+0:5](=[O;H0;D1;+0:4])-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:12] | 82.6 | [{"value": 82.6, "product": "NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)C)=O)C(=O)C1=CC(=CC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.5, "product": "NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)C)=O)C(=O)C1=CC(=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of intermediate 19 (0.071 mol) in THF (250 ml) was cooled on an ice bath. TiCl3 15% in water (250 ml) was added dropwise. The mixture was stirred at room temperature overnight, then poured out into ice water and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was e... | 10.6084/m9.figshare.5104873.v1 | null | null | Ketone.Primary amine | c1ccc2nocc2c1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | null | O.C1CCOC1 | null | 8 | Cc1ccc(C(=O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1>O.C1CCOC1>Cc1ccc(C(=O)c2ccc(N)c(C(=O)c3cccc(Cl)c3)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2db6989bc5c143c3b9173ee3da57c93d | Cc1ccc(C(=O)c2ccc(N)c(C(=O)c3cccc(Cl)c3)c2)cc1.O=C(Cl)C(Cl)(Cl)Cl>>Cc1ccc(C(=O)c2ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c3cccc(Cl)c3)c2)cc1 | ClC(C(=O)Cl)(Cl)Cl.C(C)N(CC)CC.NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)C)=O)C(=O)C1=CC(=CC=C1)Cl>>ClC(C(=O)NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)C)=O)C(C1=CC(=CC=C1)Cl)=O)(Cl)Cl | [CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([NH2:12])[c:19]([C:20](=[O:21])[c:22]3[cH:23][cH:24][cH:25][c:26]([Cl:27])[cH:28]3)[cH:29]2)[cH:30][cH:31]1.Cl[C:13](=[O:14])[C:15]([Cl:16])([Cl:17])[Cl:18]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])... | Cc1ccc(C(=O)c2ccc(N)c(C(=O)c3cccc(Cl)c3)c2)cc1.O=C(Cl)C(Cl)(Cl)Cl | Cc1ccc(C(=O)c2ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c3cccc(Cl)c3)c2)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(c1ccccc1)c1cccc(C(=O)c2ccccc2)c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[Cl;D1;H0:4])(-[Cl;D1;H0:5])-[Cl;D1;H0:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]-[C:11]=[O;D1;H0:12]>>[Cl;D1;H0:4]-[C:3](-[Cl;D1;H0:5])(-[Cl;D1;H0:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]-[C:11]=[O;D1;H0:12] | 99.8 | [{"value": 99.8, "product": "ClC(C(=O)NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)C)=O)C(C1=CC(=CC=C1)Cl)=O)(Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Intermediate 20 (0.0085 mol) was added at 5° C. to DCM (30 ml) under N2 flow. trichloro-acetyl chloride (0.01 mol) then triethylamine (0.01 mol) were added dropwise. The mixture was brought to room temperature, stirred at room temperature for 3 hours, poured out into ice water and extracted with DCM. The organic layer ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 3 | Cc1ccc(C(=O)c2ccc(N)c(C(=O)c3cccc(Cl)c3)c2)cc1.O=C(Cl)C(Cl)(Cl)Cl>C(Cl)Cl>Cc1ccc(C(=O)c2ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c3cccc(Cl)c3)c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef68f45e67c84ed5b740f889c172e6d1 | Cc1ccc(C(=O)c2ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c3cccc(Cl)c3)c2)cc1.[NH4+]>>Cc1ccc(C(=O)c2ccc3[nH]c(=O)nc(-c4cccc(Cl)c4)c3c2)cc1 | ClC(C(=O)NC1=C(C=C(C=C1)C(C1=CC=C(C=C1)C)=O)C(C1=CC(=CC=C1)Cl)=O)(Cl)Cl.[NH4+].C(C)(=O)[O-]>>ClC=1C=C(C=CC1)C1=NC(NC2=CC=C(C=C12)C(C1=CC=C(C=C1)C)=O)=O | O=[C:16]([c:17]1[cH:18][cH:19][cH:20][c:21]([Cl:22])[cH:23]1)[c:24]1[c:11]([NH:12][C:13](C(Cl)(Cl)Cl)=[O:14])[cH:10][cH:9][c:8]([C:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:27][cH:26]2)=[O:7])[cH:25]1.[NH4+:15]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]3[nH:12][c:13](=[O:14])[n:15][c:16](-[c:17... | Cc1ccc(C(=O)c2ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c3cccc(Cl)c3)c2)cc1.[NH4+] | Cc1ccc(C(=O)c2ccc3[nH]c(=O)nc(-c4cccc(Cl)c4)c3c2)cc1 | null | null | CS(=O)C | Aromatic Heterocycle Formation | OtherReaction | 34356251393ced07649e3f2d79584418a4a8dc983e24c794ec9fd18e790ecc31 | 1620ff2b4fcf2514dc5381b8c0e77d605f9d7258e5a6b5dfb277498e8a5ebb1a | O=C(c1ccccc1)c1ccc2[nH]c(=O)nc(-c3ccccc3)c2c1 | Cl-C(-Cl)(-Cl)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6](-[C;H0;D3;+0:7](=O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:13].[NH4+;D0:14]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[n;H0;D2;+0:14]:[c;H0;D3;+0:7](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[c:6](:[c:13]):[c:4](:[c:5]):[nH;D2;+0:3]:1 | 63.4 | [{"value": 63.0, "product": "ClC=1C=C(C=CC1)C1=NC(NC2=CC=C(C=C12)C(C1=CC=C(C=C1)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.4, "product": "ClC=1C=C(C=CC1)C1=NC(NC2=CC=C(C=C12)C(C1=CC=C(C=C1)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | A mixture of intermediate 21 (0.0085 mol) and acetic acid, ammonium salt (0.0169 mol) in DMSO (42 ml) was stirred at 60° C. for 4 hours then cooled and poured out into ice water. The precipitate was filtered, washed with water, taken up in warm CH3CN, filtered off and dried under a vacuo, yielding 2.02 g (63%) of 4-(3-... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Ketone.Secondary amide | null | c1ccccc1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1.c1ccccc1 | HCl | CS(=O)C | 60 | 4 | Cc1ccc(C(=O)c2ccc(NC(=O)C(Cl)(Cl)Cl)c(C(=O)c3cccc(Cl)c3)c2)cc1.[NH4+]>CS(=O)C>Cc1ccc(C(=O)c2ccc3[nH]c(=O)nc(-c4cccc(Cl)c4)c3c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bd8f502824d94ebf940f9a1a526c49ba | Cc1ccc(C(=O)c2ccc3[nH]c(=O)nc(-c4cccc(Cl)c4)c3c2)cc1.O=P(Cl)(Cl)Cl>>Cc1ccc(C(=O)c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)cc1 | ClC=1C=C(C=CC1)C1=NC(NC2=CC=C(C=C12)C(C1=CC=C(C=C1)C)=O)=O.P(=O)(Cl)(Cl)Cl>>ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(=O)C1=CC=C(C=C1)C | O=[c:13]1[nH:12][c:11]2[cH:10][cH:9][c:8]([C:6]([c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:27][cH:26]3)=[O:7])[cH:25][c:24]2[c:16](-[c:17]2[cH:18][cH:19][cH:20][c:21]([Cl:22])[cH:23]2)[n:15]1.O=P(Cl)(Cl)[Cl:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]3[n:12][c:13]([Cl:14])[n:15][c:16](-[c:17]4[cH... | Cc1ccc(C(=O)c2ccc3[nH]c(=O)nc(-c4cccc(Cl)c4)c3c2)cc1.O=P(Cl)(Cl)Cl | Cc1ccc(C(=O)c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)cc1 | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C(c1ccccc1)c1ccc2ncnc(-c3ccccc3)c2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6](:[c:7]):[nH;D2;+0:8]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6](:[c:7]):[n;H0;D2;+0:8]:1 | 70 | [{"value": 70.0, "product": "ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(=O)C1=CC=C(C=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 4 | HOUR | A mixture of intermediate 22 (0.041 mol) in phosphoryl chloride (105 ml) was stirred at 100° C. for 4 hours then cooled. The solvent was evaporated. The residue was taken up DCM. The solvent was evaporated. The residue was taken up in DCM. The mixture was poured out into ice water, basified with K2CO3 10% and extracted... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1.c1ccccc1 | HCl | null | 100 | 4 | Cc1ccc(C(=O)c2ccc3[nH]c(=O)nc(-c4cccc(Cl)c4)c3c2)cc1.O=P(Cl)(Cl)Cl>>Cc1ccc(C(=O)c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c0c0c2a6fe664cd7b77993b86272439d | Cc1ccc(C(=O)c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)cc1.Cn1ccnc1>>Cc1ccc(C(O)(c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)c2cncn2C)cc1 | [Li]CCCC.Cl[Si](CC)(CC)CC.ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(=O)C1=CC=C(C=C1)C.[Li]CCCC.CN1C=NC=C1>>ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(O)(C1=CC=C(C=C1)C)C1=CN=CN1C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]3[n:12][c:13]([Cl:14])[n:15][c:16](-[c:17]4[cH:18][cH:19][cH:20][c:21]([Cl:22])[cH:23]4)[c:24]3[cH:25]2)[cH:32][cH:33]1.[cH:26]1[cH:27][n:28][cH:29][n:30]1[CH3:31]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]([OH:7])([c:8]2[cH:9][cH:10][c:11]3[n:12][c:13]([C... | Cc1ccc(C(=O)c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)cc1.Cn1ccnc1 | Cc1ccc(C(O)(c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)c2cncn2C)cc1 | null | null | O.C1CCOC1 | C-C Coupling | OtherReaction | 05395e7d28d1a7c287cdf9872044b38b254b469c1c451b45b37d37651dd6bc83 | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1ccc(-c2ncnc3ccc(C(c4ccccc4)c4cnc[nH]4)cc23)cc1 | [C;D1;H3:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[cH;D2;+0:6]:1.[O;H0;D1;+0:7]=[C;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]>>[C;D1;H3:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]:[c;H0;D3;+0:6]:1-[C;H0;D4;+0:8](-[OH;D1;+0:7])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14] | null | [] | -70 | CELSIUS | 15 | MINUTE | 1-Methyl-1H-imidazole (0.0507 mol) was added at −70° C. to THF (90 ml) under N2 flow. nBuLi (31.5 ml) was added dropwise. The mixture was stirred at −70° C. for 15 minutes. Chlorotriethyl-silane (0.0522 mol) was added dropwise. The mixture was stirred at −70° C. for 15 minutes. nBuLi (28 ml) was added. The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1ccc2ncncc2c1.c1ccccc1.c1c[nH]cn1 | null | O.C1CCOC1 | -70 | 0.25 | Cc1ccc(C(=O)c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)cc1.Cn1ccnc1>O.C1CCOC1>Cc1ccc(C(O)(c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)c2cncn2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1fc055abe78a4989857da9219b7cb752 | Cc1ccc(C(O)(c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)c2cncn2C)cc1.[N-]=[N+]=[N-]>>Cc1ccc(C(O)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1 | ClC1=NC2=CC=C(C=C2C(=N1)C1=CC(=CC=C1)Cl)C(O)(C1=CC=C(C=C1)C)C1=CN=CN1C.[N-]=[N+]=[N-].[Na+]>>ClC=1C=C(C=CC1)C1=NC=2N(C3=CC=C(C=C13)C(O)(C1=CC=C(C=C1)C)C1=CN=CN1C)N=NN2 | Cl[c:23]1[n:22][c:14](-[c:15]2[cH:16][cH:17][cH:18][c:19]([Cl:20])[cH:21]2)[c:12]2[c:11]([cH:10][cH:9][c:8]([C:6]([c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:35][cH:34]3)([OH:7])[c:28]3[cH:29][n:30][cH:31][n:32]3[CH3:33])[cH:13]2)[n:27]1.[N-:24]=[N+:26]=[N-:25]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]([OH:7])([c:8]2[cH:9][cH:10][... | Cc1ccc(C(O)(c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)c2cncn2C)cc1.[N-]=[N+]=[N-] | Cc1ccc(C(O)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 4e0cb3e54897e660c5677e719a9c21ad2978ab17efb16dd9052e527979ac46a1 | 155f764f095c8454a4ad08aaa42f1abcb15d5bc1d4f122e4bcc624dd834362f2 | c1ccc(-c2nc3nnnn3c3ccc(C(c4ccccc4)c4cnc[nH]4)cc23)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5](:[c:6]):[n;H0;D2;+0:7]:1.[N-;H0;D1:8]=[N+;H0;D2:9]=[N-;H0;D1:10]>>[c:6]:[c:5]1:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]2:[n;H0;D2;+0:8]:[n;H0;D2;+0:10]:[n;H0;D2;+0:9]:[n;H0;D3;+0:7]:1:2 | 72.7 | [{"value": 72.7, "product": "ClC=1C=C(C=CC1)C1=NC=2N(C3=CC=C(C=C13)C(O)(C1=CC=C(C=C1)C)C1=CN=CN1C)N=NN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 2 | HOUR | A mixture of intermediate 24 (0.0105 mol) and sodium azide (0.031 mol) in DMF (70 ml) was stirred at 90° C. for 2 hours then cooled and poured out into ice water. The precipitate was filtered and taken up in DCM. The organic layer was washed with water, separated, dried (MgSO4), filtered, and the solvent was evaporated... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2ncncc2c1 | c1ccc2c(c1)cnc1nnnn12 | c1ccccc1.c1ccccc1.c1ccc2c(c1)cnc1nnnn12.c1c[nH]cn1 | Other | CN(C)C=O | 90 | 2 | Cc1ccc(C(O)(c2ccc3nc(Cl)nc(-c4cccc(Cl)c4)c3c2)c2cncn2C)cc1.[N-]=[N+]=[N-]>CN(C)C=O>Cc1ccc(C(O)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1bbf580442944608dde689b3a7fc372 | Cc1ccc(C(O)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1.O=S(Cl)Cl>>Cc1ccc(C(Cl)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1.Cl | ClC=1C=C(C=CC1)C1=NC=2N(C3=CC=C(C=C13)C(O)(C1=CC=C(C=C1)C)C1=CN=CN1C)N=NN2.S(=O)(Cl)Cl>>Cl.ClC(C=1C=C2C(=NC=3N(C2=CC1)N=NN3)C3=CC(=CC=C3)Cl)(C3=CC=C(C=C3)C)C3=CN=CN3C | O[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:35][cH:34]1)([c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[c:14](-[c:15]1[cH:16][cH:17][cH:18][c:19]([Cl:20])[cH:21]1)[n:22][c:23]1[n:24][n:25][n:26][n:27]21)[c:28]1[cH:29][n:30][cH:31][n:32]1[CH3:33].O=S([Cl:7])[Cl:36]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]([Cl:7])([c:8]2[cH:9][c... | Cc1ccc(C(O)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1.O=S(Cl)Cl | Cc1ccc(C(Cl)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1.Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | 6d9c985570d7a3f52661c667c74572d2f612d2c4fc81ba7e9dc85123f9e01aa3 | 8285cf7af1061d4e517653bb3812cef162cb49ef59cff39f31a19b6e110ce1b3 | c1ccc(-c2nc3nnnn3c3ccc(C(c4ccccc4)c4cnc[nH]4)cc23)cc1 | O-[C;H0;D4;+0:1](-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1-[C;D1;H3:7])(-[c:8](:[c:9]):[c:10])-[c:11](:[c:12]):[c:13].O=S(-[Cl;H0;D1;+0:14])-[Cl;H0;D1;+0:15]>>[C;D1;H3:7]-[#7;a:6]1:[c:5]:[#7;a:4]:[c:3]:[c:2]:1-[C;H0;D4;+0:1](-[Cl;H0;D1;+0:15])(-[c:8](:[c:9]):[c:10])-[c:11](:[c:12]):[c:13].[ClH;D0;+0:14] | null | [] | 60 | CELSIUS | 3 | HOUR | A mixture of intermediate 25 (0.0083 mol) in thionyl chloride (80 ml) was stirred at 60° C. for 3 hours, then cooled and the solvent was evaporated. The residue was taken up in DCM. The solvent was evaporated, yielding 7-[chloro(1-methyl-1H-imidazol-5-yl)(4-methylphenyl)methyl]-5-(3-chlorophenyl)-tetrazolo[1,5-a]quinaz... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | Tertiary halide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)cnc1nnnn12.c1c[nH]cn1 | Other | null | 60 | 3 | Cc1ccc(C(O)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1.O=S(Cl)Cl>>Cc1ccc(C(Cl)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a3801d7d96d54cd2841fea0fa8ce85b6 | CC(C)O.Cc1ccc(C(Cl)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1.N>>Cc1ccc(C(N)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1.O | Cl.ClC(C=1C=C2C(=NC=3N(C2=CC1)N=NN3)C3=CC(=CC=C3)Cl)(C3=CC=C(C=C3)C)C3=CN=CN3C.N.CC(C)O>>O.ClC=1C=C(C=CC1)C1=NC=2N(C3=CC=C(C=C13)C(N)(C1=CC=C(C=C1)C)C1=CN=CN1C)N=NN2 | CC(C)[OH:36].Cl[C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:35][cH:34]1)([c:8]1[cH:9][cH:10][c:11]2[c:12]([cH:13]1)[c:14](-[c:15]1[cH:16][cH:17][cH:18][c:19]([Cl:20])[cH:21]1)[n:22][c:23]1[n:24][n:25][n:26][n:27]21)[c:28]1[cH:29][n:30][cH:31][n:32]1[CH3:33].[NH3:7]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH2:7])([c:8]2[cH:... | CC(C)O.Cc1ccc(C(Cl)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1.N | Cc1ccc(C(N)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1.O | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | cf04ad9dce2274e5d9a9cf24ee98c82defb9d00439b93dd2f2631fff7c8e202d | fb14544c66fca0b0883c6ebde415427401efbd881d01e0b9a902aed208e1aa10 | c1ccc(-c2nc3nnnn3c3ccc(C(c4ccccc4)c4cnc[nH]4)cc23)cc1 | C-C(-C)-[OH;D1;+0:1].Cl-[C;H0;D4;+0:2](-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1-[C;D1;H3:8])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14].[NH3;D0;+0:15]>>[C;D1;H3:8]-[#7;a:7]1:[c:6]:[#7;a:5]:[c:4]:[c:3]:1-[C;H0;D4;+0:2](-[NH2;D1;+0:15])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14].[OH2;D0;+0:1] | 33 | [{"value": 33.0, "product": "O.ClC=1C=C(C=CC1)C1=NC=2N(C3=CC=C(C=C13)C(N)(C1=CC=C(C=C1)C)C1=CN=CN1C)N=NN2", "details": "PERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 1 | HOUR | A mixture of intermediate 26 (0.0083 mol) in THF (80 ml) was cooled to 5° C. under N2 flow. NH3/iPrOH (80 ml) was added dropwise. The mixture was stirred at 5° C. for 1 hours, then brought to room temperature. The mixture was stirred at room temperature overnight, poured out into ice water and extracted with DCM. The o... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Secondary alcohol | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)cnc1nnnn12.c1c[nH]cn1 | HCl | C1CCOC1 | 5 | 1 | CC(C)O.Cc1ccc(C(Cl)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1.N>C1CCOC1>Cc1ccc(C(N)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1.O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8deae60c94284616a589f5ea5b9930c6 | Cc1ccc(C(N)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1>>Cc1ccc(C(N)(c2ccc3c(c2)C(c2cccc(Cl)c2)Nc2nnnn2-3)c2cncn2C)cc1 | C(Cl)Cl.[B-].[Na+].O.ClC=1C=C(C=CC1)C1=NC=2N(C3=CC=C(C=C13)C(N)(C1=CC=C(C=C1)C)C1=CN=CN1C)N=NN2>>ClC=1C=C(C=CC1)C1NC=2N(C3=CC=C(C=C13)C(N)(C1=CC=C(C=C1)C)C1=CN=CN1C)N=NN2 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH2:7])([c:8]2[cH:9][cH:10][c:11]3[c:12]([cH:13]2)[c:14](-[c:15]2[cH:16][cH:17][cH:18][c:19]([Cl:20])[cH:21]2)[n:22][c:23]2[n:24][n:25][n:26][n:27]32)[c:28]2[cH:29][n:30][cH:31][n:32]2[CH3:33])[cH:34][cH:35]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH2:7])([c:8]2[cH:9][cH:10][c:11]3... | Cc1ccc(C(N)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1 | Cc1ccc(C(N)(c2ccc3c(c2)C(c2cccc(Cl)c2)Nc2nnnn2-3)c2cncn2C)cc1 | null | null | CO | Reduction | OtherReaction | 68fa0e5ecb7fd022bbef2c0545f4aab67cdefa951d7696965b374d746a3ba330 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | c1ccc(C2Nc3nnnn3-c3ccc(C(c4ccccc4)c4cnc[nH]4)cc32)cc1 | [c:1]:[c:2]1:[c;H0;D3;+0:3](:[c:4]:[c:5]):[n;H0;D3;+0:6]2:[#7;a:7]:[#7;a:8]:[#7;a:9]:[c:10]:2:[n;H0;D2;+0:11]:[c;H0;D3;+0:12]:1-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[c:1]:[c:2]1:[c;H0;D3;+0:3](:[c:4]:[c:5])-[n;H0;D3;+0:6]2:[#7;a:7]:[#7;a:8]:[#7;a:9]:[c:10]:2-[NH;D2;+0:11]-[CH;D3;+0:12]-1-[c;H0;D3;+0:13](:[c:1... | 29 | [{"value": 28.0, "product": "ClC=1C=C(C=CC1)C1NC=2N(C3=CC=C(C=C13)C(N)(C1=CC=C(C=C1)C)C1=CN=CN1C)N=NN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.0, "product": "ClC=1C=C(C=CC1)C1NC=2N(C3=CC=C(C=C13)C(N)(C1=CC=C(C=C1)C)C1=CN=CN1C)N=NN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Sodium hydroborate (0.0005 mol) was added portionwise at room temperature to a mixture of intermediate 27 (0.0005 mol) in methanol (2.5 ml). The mixture was stirred at room temperature for 2 hours and poured out into ice water. DCM was added. The mixture was extracted with DCM. The organic layer was separated, washed w... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccc2c(c1)cnc1nnnn12 | c1ccc2c(c1)CNc1nnnn12 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CNc1nnnn12.c1c[nH]cn1 | null | CO | null | 2 | Cc1ccc(C(N)(c2ccc3c(c2)c(-c2cccc(Cl)c2)nc2nnnn23)c2cncn2C)cc1>CO>Cc1ccc(C(N)(c2ccc3c(c2)C(c2cccc(Cl)c2)Nc2nnnn2-3)c2cncn2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-62b1e8b94e0e40819a548a7747a6c92b | Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2c(c1)C(c1cccc(Cl)c1)Nc1nnnn1-2>>Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2c(c1)C(c1cccc(Cl)c1)n1nnnc1N2 | ClC=1C=C(C=CC1)C1NC=2N(C3=CC=C(C=C13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)F)N=NN2>>ClC=1C=C(C=CC1)C1N2C(NC=3C=CC(=CC13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)F)=NN=N2 | [CH3:1][n:2]1[cH:3][n:4][cH:5][c:6]1[C:7]([OH:8])([c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1)[c:16]1[cH:17][cH:18][c:19]2[c:20]([cH:21]1)[CH:22]([c:23]1[cH:24][cH:25][cH:26][c:27]([Cl:28])[cH:29]1)[NH:30][c:34]1[n:33][n:32][n:31][n:35]1-2>>[CH3:1][n:2]1[cH:3][n:4][cH:5][c:6]1[C:7]([OH:8])([c:9]1[cH:10][cH:11][c:... | Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2c(c1)C(c1cccc(Cl)c1)Nc1nnnn1-2 | Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2c(c1)C(c1cccc(Cl)c1)n1nnnc1N2 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 9cbfd0d2b6f07cab6074b89f8abb2208b435e69c8c7659d1f6d9527cea17dc98 | 5599dd978d687c53db7fabb5eef54650a477ffd906dc8d69ec8c4f7876adabe2 | c1ccc(C(c2ccc3c(c2)C(c2ccccc2)n2nnnc2N3)c2cnc[nH]2)cc1 | [c:1]:[c:2]:[c;H0;D3;+0:3]1:[c:4](:[c:5])-[C:6](-[c:7])-[NH;D2;+0:8]-[c:9]2:[#7;a:10]:[#7;a:11]:[n;H0;D2;+0:12]:[n;H0;D3;+0:13]:2-1>>[c:1]:[c:2]:[c;H0;D3;+0:3]1:[c:4](:[c:5])-[C:6](-[c:7])-[n;H0;D3;+0:8]2:[n;H0;D2;+0:12]:[#7;a:11]:[#7;a:10]:[c:9]:2-[NH;D2;+0:13]-1 | 51.2 | [{"value": 50.0, "product": "ClC=1C=C(C=CC1)C1N2C(NC=3C=CC(=CC13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)F)=NN=N2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.2, "product": "ClC=1C=C(C=CC1)C1N2C(NC=3C=CC(=CC13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)F)=NN=N2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of intermediate 9 (0.0014 mol) in toluene (10 ml) was stirred and refluxed for 48 hours, then brought to room temperature and the solvent was evaporated till dryness. The residue was taken up in DCM. The solvent was evaporated till dryness. The residue was purified by column chromatography over kromasil® (10 ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Secondary amine | c1ccc2c(c1)CNc1nnnn12 | c1ccc2c(c1)Cn1nnnc1N2 | c1cnc[nH]1.c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1nnnc1N2 | null | C1(=CC=CC=C1)C | null | null | Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2c(c1)C(c1cccc(Cl)c1)Nc1nnnn1-2>C1(=CC=CC=C1)C>Cn1cncc1C(O)(c1ccc(F)cc1)c1ccc2c(c1)C(c1cccc(Cl)c1)n1nnnc1N2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee20223f472244bfac1603ceaa338f24 | COc1ccc(C(O)(c2ccc3c(c2)C(c2cccc(Cl)c2)Nc2nnnn2-3)c2cncn2C)cc1>>COc1ccc(C(O)(c2ccc3c(c2)C(c2cccc(Cl)c2)n2nnnc2N3)c2cncn2C)cc1 | ClC=1C=C(C=CC1)C1NC=2N(C3=CC=C(C=C13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)OC)N=NN2>>ClC=1C=C(C=CC1)C1N2C(NC=3C=CC(=CC13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)OC)=NN=N2 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([OH:8])([c:9]2[cH:10][cH:11][c:12]3[c:13]([cH:14]2)[CH:15]([c:16]2[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]2)[NH:23][c:27]2[n:26][n:25][n:24][n:28]2-3)[c:29]2[cH:30][n:31][cH:32][n:33]2[CH3:34])[cH:35][cH:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]([OH:8])([c:9]2[cH:10][c... | COc1ccc(C(O)(c2ccc3c(c2)C(c2cccc(Cl)c2)Nc2nnnn2-3)c2cncn2C)cc1 | COc1ccc(C(O)(c2ccc3c(c2)C(c2cccc(Cl)c2)n2nnnc2N3)c2cncn2C)cc1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 9cbfd0d2b6f07cab6074b89f8abb2208b435e69c8c7659d1f6d9527cea17dc98 | 5599dd978d687c53db7fabb5eef54650a477ffd906dc8d69ec8c4f7876adabe2 | c1ccc(C(c2ccc3c(c2)C(c2ccccc2)n2nnnc2N3)c2cnc[nH]2)cc1 | [c:1]:[c:2]:[c;H0;D3;+0:3]1:[c:4](:[c:5])-[C:6](-[c:7])-[NH;D2;+0:8]-[c:9]2:[#7;a:10]:[#7;a:11]:[n;H0;D2;+0:12]:[n;H0;D3;+0:13]:2-1>>[c:1]:[c:2]:[c;H0;D3;+0:3]1:[c:4](:[c:5])-[C:6](-[c:7])-[n;H0;D3;+0:8]2:[n;H0;D2;+0:12]:[#7;a:11]:[#7;a:10]:[c:9]:2-[NH;D2;+0:13]-1 | 27 | [{"value": 27.0, "product": "ClC=1C=C(C=CC1)C1N2C(NC=3C=CC(=CC13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)OC)=NN=N2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.7, "product": "ClC=1C=C(C=CC1)C1N2C(NC=3C=CC(=CC13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)OC)=NN=N2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of intermediate 17 (0.0006 mol) in toluene (10 ml) was stirred and refluxed for 5 hours, then brought to room temperature and the solvent, was evaporated till dryness. The residue was taken up in DCM. The solvent was evaporated till dryness. The residue was purified by column chromatography over kromasil® (10... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Secondary amine | c1ccc2c(c1)CNc1nnnn12 | c1ccc2c(c1)Cn1nnnc1N2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)Cn1nnnc1N2.c1c[nH]cn1 | null | C1(=CC=CC=C1)C | null | null | COc1ccc(C(O)(c2ccc3c(c2)C(c2cccc(Cl)c2)Nc2nnnn2-3)c2cncn2C)cc1>C1(=CC=CC=C1)C>COc1ccc(C(O)(c2ccc3c(c2)C(c2cccc(Cl)c2)n2nnnc2N3)c2cncn2C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f0885ae53cdd40c0bc3e07fc5ec6fe31 | CCO.Cn1cncc1C(O)(c1ccc(Cl)cc1)c1ccc2c(c1)C(c1cccc(Cl)c1)n1nnnc1N2.O>>COc1ccc(C(=O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1 | S(=O)(Cl)Cl.ClC=1C=C(C=CC1)C1N2C(NC=3C=CC(=CC13)C(O)(C1=CN=CN1C)C1=CC=C(C=C1)Cl)=NN=N2.CCO.O>>ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(=O)C2=CC=C(C=C2)OC | C[CH2:1][OH:2].Cn1cncc1[C:7]([c:6]1[cH:5][cH:4][c:3](Cl)[cH:26][cH:25]1)([OH:8])[c:9]1[cH:10][cH:11][c:12]2[c:23]([cH:24]1)[CH:15]([c:16]1[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]1)n1nnnc1[NH:13]2.[OH2:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]3[n:13][o:14][c:15](-[c:16]4[cH:17][... | CCO.Cn1cncc1C(O)(c1ccc(Cl)cc1)c1ccc2c(c1)C(c1cccc(Cl)c1)n1nnnc1N2.O | COc1ccc(C(=O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1 | null | null | C(Cl)Cl | Acylation | OtherReaction | b68ed1a6e78323296df0c70e8a7f898f2bf257898deedcee227a2db14e9afb08 | 3f2ec67fe5b8665c3f7e857fb9a10a89e35b1acb414473f30dcf33bfc4774a11 | O=C(c1ccccc1)c1ccc2noc(-c3ccccc3)c2c1 | C-[CH2;D2;+0:1]-[OH;D1;+0:2].C-n1:c:n:c:c:1-[C;H0;D4;+0:3](-[OH;D1;+0:4])(-[c:5]1:[c:6]:[c:7]:[c;H0;D3;+0:8](-Cl):[c:9]:[c:10]:1)-[c:11]1:[c:12]:[c:13]:[c:14]2:[c:15](:[c:16]:1)-[CH;D3;+0:17](-[c;H0;D3;+0:18](:[c:19]:[c:20]):[c:21]:[c:22])-n1:n:n:n:c:1-[NH;D2;+0:23]-2.[OH2;D0;+0:24]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c;H0;... | 17 | [{"value": 17.0, "product": "ClC=1C=C(C=CC1)C=1ON=C2C1C=C(C=C2)C(=O)C2=CC=C(C=C2)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Thionyl chloride (0.1 ml) was added at room temperature to a mixture of compound 1 (0.0002 mol) in EtOH (2 ml). The mixture was stirred at room temperature for 2 hours. Water was added. The mixture was taken up in DCM. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol.Tertiary alcohol.Secondary amine | Ketone.Ether | c1c[nH]cn1.c1ccccc1.c1ccc2c(c1)Cn1nnnc1N2 | c1ccccc1.c1ccc2nocc2c1 | c1ccccc1.c1ccc2nocc2c1.c1ccccc1 | HCl | C(Cl)Cl | null | 2 | CCO.Cn1cncc1C(O)(c1ccc(Cl)cc1)c1ccc2c(c1)C(c1cccc(Cl)c1)n1nnnc1N2.O>C(Cl)Cl>COc1ccc(C(=O)c2ccc3noc(-c4cccc(Cl)c4)c3c2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e6dc98f870d84313bb53e8114f279824 | O=C(O)C1(c2ccc(Cl)cc2)CCC1.OCC1CCCNC1>>O=C(N1CCCC(CO)C1)C1(c2ccc(Cl)cc2)CCC1 | N1CC(CCC1)CO.ClC1=CC=C(C=C1)C1(CCC1)C(=O)O.C(C)(C)N(CC)C(C)C.C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F>>ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CO | O[C:2](=[O:1])[C:11]1([c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[CH2:19][CH2:20][CH2:21]1.[NH:3]1[CH2:4][CH2:5][CH2:6][CH:7]([CH2:8][OH:9])[CH2:10]1>>[O:1]=[C:2]([N:3]1[CH2:4][CH2:5][CH2:6][CH:7]([CH2:8][OH:9])[CH2:10]1)[C:11]1([c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[CH2:19][CH2:20][CH2:21]1 | O=C(O)C1(c2ccc(Cl)cc2)CCC1.OCC1CCCNC1 | O=C(N1CCCC(CO)C1)C1(c2ccc(Cl)cc2)CCC1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(N1CCCCC1)C1(c2ccccc2)CCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])(-[C:5])-[C:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:5]-[C:3](-[c:4])(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9](-[C:10]-[C:11])-[C:8]-[C:7])-[C:6] | 43.4 | [{"value": 43.4, "product": "ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a solution of 3-piperidinemethanol (5.0 g, 43.4 mmol), 1-(4-chlorophenyl)-1-cyclobutanecarboxylic acid (9.14 g, 43.4 mmol), and diisopropylethylamine (11.22 g, 86.8 mmol) in dichloromethane (100 mL) at 0° C. was added PyBroP® (22.26 g, 47.8 mmol). The reaction was stirred at 0° C. for 1 h and then at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.C1CCC1 | HO- | ClCCl | 0 | 1 | O=C(O)C1(c2ccc(Cl)cc2)CCC1.OCC1CCCNC1>ClCCl>O=C(N1CCCC(CO)C1)C1(c2ccc(Cl)cc2)CCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1c0863060bf5429485d5a823cc840c77 | CS(=O)(=O)Cl.O=C(N1CCCC(CO)C1)C1(c2ccc(Cl)cc2)CCC1>>CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1 | ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CO.C(C)N(CC)CC.CS(=O)(=O)Cl>>ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)COS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][N:11]([C:12](=[O:13])[C:14]2([c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]3)[CH2:22][CH2:23][CH2:24]2)[CH2:25]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][N:11]([C:12](=[O:13])[C:14]2([c:15]3[cH:16][cH:17][c:18]([... | CS(=O)(=O)Cl.O=C(N1CCCC(CO)C1)C1(c2ccc(Cl)cc2)CCC1 | CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | O=C(N1CCCCC1)C1(c2ccccc2)CCC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 71 | [{"value": 71.0, "product": "ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)COS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.7, "product": "ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)COS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | The amide derivative 1 (5.0 g, 16.3 mmol) was dissolved in dichloromethane (50 mL) and cooled to 0° C. To this solution was added triethylamine (5.0 mL) followed by dropwise addition of methanesulfonyl chloride (2.05 g, 17.9 mmol). The reaction was stirred at 0 C. for 1 h, and then at room temperature overnight. The re... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]CC1.c1ccccc1.C1CCC1 | HCl | ClCCl | 0 | 1 | CS(=O)(=O)Cl.O=C(N1CCCC(CO)C1)C1(c2ccc(Cl)cc2)CCC1>ClCCl>CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f55b5e0e1b34aed9a393af46d3bc746 | COc1ccccc1N1CCNCC1.CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1>>COc1ccccc1N1CCN(CC2CCCN(C(=O)C3(c4ccc(Cl)cc4)CCC3)C2)CC1 | ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)COS(=O)(=O)C.COC1=C(C=CC=C1)N1CCNCC1.C(C)N(CC)CC>>ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][NH:12][CH2:33][CH2:34]1.CS(=O)(=O)O[CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][N:18]([C:19](=[O:20])[C:21]2([c:22]3[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]3)[CH2:29][CH2:30][CH2:31]2)[CH2:32]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[... | COc1ccccc1N1CCNCC1.CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1 | COc1ccccc1N1CCN(CC2CCCN(C(=O)C3(c4ccc(Cl)cc4)CCC3)C2)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Alkylation of amines | 1bf281a76f5d92191240c4561d80a265a934eb351041bae69548607f60e915b2 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=C(N1CCCC(CN2CCN(c3ccccc3)CC2)C1)C1(c2ccccc2)CCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#7:5]-[C:4]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1)-[C:3] | 43.1 | [{"value": 43.0, "product": "ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.1, "product": "ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2 (1.0 g, 2.60 mmol) in acetonitrile (25 mL) was added 1-(2-methoxyphenyl)piperazine (0.55 g, 2.86 mmol) and triethylamine (2 mL). The reaction was stirred and refluxed for 20 h. After cooling to room temperature, most of solvent was removed by rotary evaporation. The reaction mixture was partitioned b... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.C1CC[NH]CC1.c1ccccc1.C1CCC1 | MsOH.HO- | C(C)#N | null | null | COc1ccccc1N1CCNCC1.CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1>C(C)#N>COc1ccccc1N1CCN(CC2CCCN(C(=O)C3(c4ccc(Cl)cc4)CCC3)C2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-839499243f7b4daead6dc6bd98c0c6c8 | CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1.Clc1ccccc1N1CCNCC1>>O=C(N1CCCC(CN2CCN(c3ccccc3Cl)CC2)C1)C1(c2ccc(Cl)cc2)CCC1 | ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)COS(=O)(=O)C.ClC1=C(C=CC=C1)N1CCNCC1.C([O-])([O-])=O.[Cs+].[Cs+]>>ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)Cl | CS(=O)(=O)O[CH2:8][CH:7]1[CH2:6][CH2:5][CH2:4][N:3]([C:2](=[O:1])[C:23]2([c:24]3[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]3)[CH2:31][CH2:32][CH2:33]2)[CH2:22]1.[NH:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[Cl:19])[CH2:20][CH2:21]1>>[O:1]=[C:2]([N:3]1[CH2:4][CH2:5][CH2:6][CH:7]([CH2:8][N:9]2[... | CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1.Clc1ccccc1N1CCNCC1 | O=C(N1CCCC(CN2CCN(c3ccccc3Cl)CC2)C1)C1(c2ccc(Cl)cc2)CCC1 | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=C(N1CCCC(CN2CCN(c3ccccc3)CC2)C1)C1(c2ccccc2)CCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#7:5]-[C:4]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1)-[C:3] | 42 | [{"value": 42.0, "product": "ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.9, "product": "ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound 7 was prepared using the method of described in Example 3, starting with compound 2 (1.0 g, 2.60 mmol), 1-(2-chlorophenyl)piperazine (0.56 g, 2.86 mmol), and cesium carbonate (1.27 g, 3.90 mmol) to give 7 (0.53 g, 42%); C27H33Cl2N3O, LRMS (m/z)=487 (MH+).
Conditions: See reaction.notes.procedure_details.
Worku... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.C1CCC1 | MsOH.HO- | null | null | null | CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1.Clc1ccccc1N1CCNCC1>>O=C(N1CCCC(CN2CCN(c3ccccc3Cl)CC2)C1)C1(c2ccc(Cl)cc2)CCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e6d3ae6968eb4aeebe2edddb0e93582c | CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1.Fc1ccccc1N1CCNCC1>>O=C(N1CCCC(CN2CCN(c3ccccc3F)CC2)C1)C1(c2ccc(Cl)cc2)CCC1 | ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)COS(=O)(=O)C.FC1=C(C=CC=C1)N1CCNCC1.C([O-])([O-])=O.[Cs+].[Cs+]>>ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)F | CS(=O)(=O)O[CH2:8][CH:7]1[CH2:6][CH2:5][CH2:4][N:3]([C:2](=[O:1])[C:23]2([c:24]3[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]3)[CH2:31][CH2:32][CH2:33]2)[CH2:22]1.[NH:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[F:19])[CH2:20][CH2:21]1>>[O:1]=[C:2]([N:3]1[CH2:4][CH2:5][CH2:6][CH:7]([CH2:8][N:9]2[C... | CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1.Fc1ccccc1N1CCNCC1 | O=C(N1CCCC(CN2CCN(c3ccccc3F)CC2)C1)C1(c2ccc(Cl)cc2)CCC1 | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=C(N1CCCC(CN2CCN(c3ccccc3)CC2)C1)C1(c2ccccc2)CCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#7:5]-[C:4]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1)-[C:3] | 46 | [{"value": 46.0, "product": "ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.8, "product": "ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound 8 was prepared using the method described in Example 3, starting with compound 2 (1.0 g, 2.60 mmol), 1-(2-fluorophenyl)piperazine (0.51 g, 2.86 mmol), and cesium carbonate (1.27 g, 3.90 mmol) to give 8 (0.56 g, 46%); C27H33ClFN3O, LRMS (m/z)=471 (MH+).
Conditions: See reaction.notes.procedure_details.
Workup: ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.C1CCC1 | MsOH.HO- | null | null | null | CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1.Fc1ccccc1N1CCNCC1>>O=C(N1CCCC(CN2CCN(c3ccccc3F)CC2)C1)C1(c2ccc(Cl)cc2)CCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1eff77d0a8f94fd79d80d99e54259ac7 | CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1.FC(F)(F)Oc1ccccc1N1CCNCC1>>O=C(N1CCCC(CN2CCN(c3ccccc3OC(F)(F)F)CC2)C1)C1(c2ccc(Cl)cc2)CCC1 | ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)COS(=O)(=O)C.FC(OC1=C(C=CC=C1)N1CCNCC1)(F)F.C([O-])([O-])=O.[Cs+].[Cs+]>>ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)OC(F)(F)F | CS(=O)(=O)O[CH2:8][CH:7]1[CH2:6][CH2:5][CH2:4][N:3]([C:2](=[O:1])[C:27]2([c:28]3[cH:29][cH:30][c:31]([Cl:32])[cH:33][cH:34]3)[CH2:35][CH2:36][CH2:37]2)[CH2:26]1.[NH:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[O:19][C:20]([F:21])([F:22])[F:23])[CH2:24][CH2:25]1>>[O:1]=[C:2]([N:3]1[CH2:4][CH2:5][... | CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1.FC(F)(F)Oc1ccccc1N1CCNCC1 | O=C(N1CCCC(CN2CCN(c3ccccc3OC(F)(F)F)CC2)C1)C1(c2ccc(Cl)cc2)CCC1 | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=C(N1CCCC(CN2CCN(c3ccccc3)CC2)C1)C1(c2ccccc2)CCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#7:5]-[C:4]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1)-[C:3] | 32.3 | [{"value": 32.0, "product": "ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)OC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.3, "product": "ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)OC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound 9 was prepared using the method described in Example 3, starting with compound 2 (1.0 g, 2.60 mmol), 1-(2-trifluoromethoxyphenyl)piperazine (0.70 g, 2.86 mmol), and cesium carbonate (1.27 g, 3.90 mmol) to give 9 (0.45 g, 32%); C28H33ClF3N3O2, LRMS (m/z)=537 (MH+).
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.C1CCC1 | MsOH.HO- | null | null | null | CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1.FC(F)(F)Oc1ccccc1N1CCNCC1>>O=C(N1CCCC(CN2CCN(c3ccccc3OC(F)(F)F)CC2)C1)C1(c2ccc(Cl)cc2)CCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e826ef96d0254473a066b1b2039e0662 | CC(C)Oc1ccccc1N1CCNCC1.CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1>>CC(C)Oc1ccccc1N1CCN(CC2CCCN(C(=O)C3(c4ccc(Cl)cc4)CCC3)C2)CC1 | ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)COS(=O)(=O)C.C(C)(C)OC1=C(C=CC=C1)N1CCNCC1.C([O-])([O-])=O.[Cs+].[Cs+]>>ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)OC(C)C | [CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[N:11]1[CH2:12][CH2:13][NH:14][CH2:35][CH2:36]1.CS(=O)(=O)O[CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][N:20]([C:21](=[O:22])[C:23]2([c:24]3[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]3)[CH2:31][CH2:32][CH2:33]2)[CH2:34]1>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6... | CC(C)Oc1ccccc1N1CCNCC1.CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1 | CC(C)Oc1ccccc1N1CCN(CC2CCCN(C(=O)C3(c4ccc(Cl)cc4)CCC3)C2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | 1bf281a76f5d92191240c4561d80a265a934eb351041bae69548607f60e915b2 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=C(N1CCCC(CN2CCN(c3ccccc3)CC2)C1)C1(c2ccccc2)CCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#7:5]-[C:4]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1)-[C:3] | 37 | [{"value": 37.0, "product": "ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)OC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.9, "product": "ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)OC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound 11 was prepared using the method described in Example 3, starting with compound 2 (1.0 g, 2.60 mmol), 1-(2-isopropoxyphenyl)piperazine (0.63 g, 2.86 mmol), and cesium carbonate (1.27 g, 3.90 mmol) to give 11 (0.49 g, 37%); C30H40ClN3O2, LRMS (m/z)=511 (MH+).
Conditions: See reaction.notes.procedure_details.
Wo... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.C1CC[NH]CC1.c1ccccc1.C1CCC1 | MsOH.HO- | null | null | null | CC(C)Oc1ccccc1N1CCNCC1.CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1>>CC(C)Oc1ccccc1N1CCN(CC2CCCN(C(=O)C3(c4ccc(Cl)cc4)CCC3)C2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-84a165eb047144dd97ead8cb0ccc328c | CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1.Oc1ccccc1N1CCNCC1>>O=C(N1CCCC(CN2CCN(c3ccccc3O)CC2)C1)C1(c2ccc(Cl)cc2)CCC1 | ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)COS(=O)(=O)C.OC1=C(C=CC=C1)N1CCNCC1.C([O-])([O-])=O.[Cs+].[Cs+]>>ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)O | CS(=O)(=O)O[CH2:8][CH:7]1[CH2:6][CH2:5][CH2:4][N:3]([C:2](=[O:1])[C:23]2([c:24]3[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]3)[CH2:31][CH2:32][CH2:33]2)[CH2:22]1.[NH:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[OH:19])[CH2:20][CH2:21]1>>[O:1]=[C:2]([N:3]1[CH2:4][CH2:5][CH2:6][CH:7]([CH2:8][N:9]2[... | CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1.Oc1ccccc1N1CCNCC1 | O=C(N1CCCC(CN2CCN(c3ccccc3O)CC2)C1)C1(c2ccc(Cl)cc2)CCC1 | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=C(N1CCCC(CN2CCN(c3ccccc3)CC2)C1)C1(c2ccccc2)CCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#7:5]-[C:4]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1)-[C:3] | 32 | [{"value": 32.0, "product": "ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.0, "product": "ClC1=CC=C(C=C1)C1(CCC1)C(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound 12 was prepared using the method described in Example 3, starting with compound 2 (1.0 g, 2.60 mmol), 1-(2-hydroxyphenyl)piperazine (0.51 g, 2.86 mmol), and cesium carbonate (1.27 g, 3.90 mmol) to give 12 (0.39 g, 32%); C27H34ClN3O2, LRMS (m/z)=469 (MH+).
Conditions: See reaction.notes.procedure_details.
Worku... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1CC[NH]CC1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.C1CCC1 | MsOH.HO- | null | null | null | CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCC2)C1.Oc1ccccc1N1CCNCC1>>O=C(N1CCCC(CN2CCN(c3ccccc3O)CC2)C1)C1(c2ccc(Cl)cc2)CCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1de4723cb91b4f48ba6cf29426e8ae90 | CC(C)(C)OC(=O)N1CCCC(CO)C1.CS(=O)(=O)Cl>>CC(C)(C)OC(=O)N1CCCC(COS(C)(=O)=O)C1 | CS(=O)(=O)Cl.C(C)(C)(C)OC(=O)N1CC(CCC1)CO.CCN(C(C)C)C(C)C>>C(C)(C)(C)OC(=O)N1CC(CCC1)COS(=O)(=O)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH:12]([CH2:13][OH:14])[CH2:19]1.Cl[S:15]([CH3:16])(=[O:17])=[O:18]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH:12]([CH2:13][O:14][S:15]([CH3:16])(=[O:17])=[O:18])[CH2:19]1 | CC(C)(C)OC(=O)N1CCCC(CO)C1.CS(=O)(=O)Cl | CC(C)(C)OC(=O)N1CCCC(COS(C)(=O)=O)C1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | C1CCNCC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 86 | [{"value": 86.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (9.41 g, 0.048 mol) in dichloromethane (200 mL) at room temperature was added iPr2NEt (14.1 g, 0.110 mol), followed by MsCl (5.5 g, 0.048 mol). The reaction mixture was allowed to stir for one hour before concentrating and purifying the resu... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]CC1 | HCl | ClCCl | null | 1 | CC(C)(C)OC(=O)N1CCCC(CO)C1.CS(=O)(=O)Cl>ClCCl>CC(C)(C)OC(=O)N1CCCC(COS(C)(=O)=O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-987342903f5641e0bac10390d6fc29ed | CC(C)(C)OC(=O)N1CCCC(COS(C)(=O)=O)C1.COc1ccccc1N1CCNCC1>>COc1ccccc1N1CCN(CC2CCCN(C(=O)OC(C)(C)C)C2)CC1 | COC1=C(C=CC=C1)N1CCNCC1.C(C)(C)(C)OC(=O)N1CC(CCC1)COS(=O)(=O)C.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)(C)OC(=O)N1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)OC | CS(=O)(=O)O[CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][NH:12][CH2:27][CH2:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([CH2:13][CH:14]2[CH2:15... | CC(C)(C)OC(=O)N1CCCC(COS(C)(=O)=O)C1.COc1ccccc1N1CCNCC1 | COc1ccccc1N1CCN(CC2CCCN(C(=O)OC(C)(C)C)C2)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Alkylation of amines | 1bf281a76f5d92191240c4561d80a265a934eb351041bae69548607f60e915b2 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | c1ccc(N2CCN(CC3CCCNC3)CC2)cc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#7:5]-[C:4]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1)-[C:3] | null | [] | null | null | null | null | To a solution of 3-methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester (11.06 g, 0.04 mol) in acetonitrile (180 mL) was added potassium carbonate (26 g, 0.19 mol) followed by 1-(2-methoxy-phenyl) piperazine (7.25 g, 0.04 mol). After completion of addition the reaction mixture was heated to reflux. Af... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.C1CC[NH]CC1 | MsOH.HO- | C(C)#N | null | null | CC(C)(C)OC(=O)N1CCCC(COS(C)(=O)=O)C1.COc1ccccc1N1CCNCC1>C(C)#N>COc1ccccc1N1CCN(CC2CCCN(C(=O)OC(C)(C)C)C2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3d2ddcff4e1c4aee8e997e55b2747644 | O=C(O)C1(c2ccc(Cl)cc2)CCCC1.OCC1CCCNC1>>O=C(N1CCCC(CO)C1)C1(c2ccc(Cl)cc2)CCCC1 | C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F.N1CC(CCC1)CO.ClC1=CC=C(C=C1)C1(CCCC1)C(=O)O.C(C)(C)N(CC)C(C)C>>ClC1=CC=C(C=C1)C1(CCCC1)C(=O)N1CC(CCC1)CO | O[C:2](=[O:1])[C:11]1([c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[CH2:19][CH2:20][CH2:21][CH2:22]1.[NH:3]1[CH2:4][CH2:5][CH2:6][CH:7]([CH2:8][OH:9])[CH2:10]1>>[O:1]=[C:2]([N:3]1[CH2:4][CH2:5][CH2:6][CH:7]([CH2:8][OH:9])[CH2:10]1)[C:11]1([c:12]2[cH:13][cH:14][c:15]([Cl:16])[cH:17][cH:18]2)[CH2:19][CH2:20][CH2:2... | O=C(O)C1(c2ccc(Cl)cc2)CCCC1.OCC1CCCNC1 | O=C(N1CCCC(CO)C1)C1(c2ccc(Cl)cc2)CCCC1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(N1CCCCC1)C1(c2ccccc2)CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])(-[C:5])-[C:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:5]-[C:3](-[c:4])(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9](-[C:10]-[C:11])-[C:8]-[C:7])-[C:6] | 156.9 | [{"value": 156.9, "product": "ClC1=CC=C(C=C1)C1(CCCC1)C(=O)N1CC(CCC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of piperdin-3-yl methanol (0.342 g, 2.97 mmol), 1-(4-chloro-phenyl)-cyclopentylcarboxylic acid (1.0 g, 4.45 mmol), diisopropylethyl amine (1.9, 15.00 mmol) in dichloromethane (7 mL) was stirred at room temperature. PyBroP (2.07 g, 4.45 mmol) was added and the reaction mixture continued stirring at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.C1CCCC1 | HO- | ClCCl | null | null | O=C(O)C1(c2ccc(Cl)cc2)CCCC1.OCC1CCCNC1>ClCCl>O=C(N1CCCC(CO)C1)C1(c2ccc(Cl)cc2)CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c5434389f3a442329f8bdc103ff7daa9 | CS(=O)(=O)Cl.O=C(N1CCCC(CO)C1)C1(c2ccc(Cl)cc2)CCCC1>>CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCCC2)C1 | CS(=O)(=O)Cl.ClC1=CC=C(C=C1)C1(CCCC1)C(=O)N1CC(CCC1)CO.CCN(C(C)C)C(C)C>>ClC1=CC=C(C=C1)C1(CCCC1)C(=O)N1CC(CCC1)COS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][N:11]([C:12](=[O:13])[C:14]2([c:15]3[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]3)[CH2:22][CH2:23][CH2:24][CH2:25]2)[CH2:26]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][N:11]([C:12](=[O:13])[C:14]2([c:15]3[cH:16][cH:17]... | CS(=O)(=O)Cl.O=C(N1CCCC(CO)C1)C1(c2ccc(Cl)cc2)CCCC1 | CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCCC2)C1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | O=C(N1CCCCC1)C1(c2ccccc2)CCCC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 56 | [{"value": 56.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of [1-(4-chloro-phenyl)-cyclopentyl]-(3-hydroxymethyl-piperidin-1-yl)-methanone (0.5 g, 1.55 mmol) in dichloromethane (9.5 mL) at room temperature was added iPr2NEt (0.5 g, 3.9 mmol) followed by MsCl (0.214 g, 1.86 mmol). The reaction mixture was allowed to stir for one hour before concentrating and purif... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]CC1.c1ccccc1.C1CCCC1 | HCl | ClCCl | null | 1 | CS(=O)(=O)Cl.O=C(N1CCCC(CO)C1)C1(c2ccc(Cl)cc2)CCCC1>ClCCl>CS(=O)(=O)OCC1CCCN(C(=O)C2(c3ccc(Cl)cc3)CCCC2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-126bbfff893842e280cfbd2c99e113f0 | CCOC(=O)C1CCCNC1.O=C(O)C1(c2ccc(Cl)cc2)CC1>>CCOC(=O)C1CCCN(C(=O)C2(c3ccc(Cl)cc3)CC2)C1 | C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)Br.F[P-](F)(F)(F)(F)F.C(C)OC(=O)C1CNCCC1.ClC1=CC=C(C=C1)C1(CC1)C(=O)O.C(C)(C)N(CC)C(C)C>>C(C)OC(=O)C1CN(CCC1)C(=O)C1(CC1)C1=CC=C(C=C1)Cl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][NH:10][CH2:23]1.O[C:11](=[O:12])[C:13]1([c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][N:10]([C:11](=[O:12])[C:13]2([c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]3)[CH2:2... | CCOC(=O)C1CCCNC1.O=C(O)C1(c2ccc(Cl)cc2)CC1 | CCOC(=O)C1CCCN(C(=O)C2(c3ccc(Cl)cc3)CC2)C1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(N1CCCCC1)C1(c2ccccc2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1(-[c:4])-[C:5]-[C:6]-1.[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]>>[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]-[C:11]-[N;H0;D3;+0:12](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1(-[c:4])-[C:5]-[C:6]-1)-[C:13]-[C:14] | 167.5 | [{"value": 167.5, "product": "C(C)OC(=O)C1CN(CCC1)C(=O)C1(CC1)C1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of piperidine-3-carboxylic acid ethyl ester (10.0 g, 0.032 mol), 1-(4-chloro-phenyl)-cyclopropylcarboxylic acid (9.57 g, 0.049 mol), diisopropylethyl amine (21.0 g, 0.16 mol) in dichloromethane (160 mL) was stirred at room temperature. PyBroP (22.6 g, 0.49 mol) was added and the reaction mixture continued st... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.C1CC1 | HO- | ClCCl | null | null | CCOC(=O)C1CCCNC1.O=C(O)C1(c2ccc(Cl)cc2)CC1>ClCCl>CCOC(=O)C1CCCN(C(=O)C2(c3ccc(Cl)cc3)CC2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eeb8b540ab9d40e081dbf145739db960 | COc1ccccc1N1CCNCC1.CS(=O)(=O)OCC1CCCN(CC2(c3ccc(Cl)cc3)CC2)C1>>COc1ccccc1N1CCN(CC2CCCN(CC3(c4ccc(Cl)cc4)CC3)C2)CC1 | C([O-])([O-])=O.[K+].[K+].ClC1=CC=C(C=C1)C1(CC1)CN1CC(CCC1)COS(=O)(=O)C.COC1=C(C=CC=C1)N1CCNCC1>>ClC1=CC=C(C=C1)C1(CC1)CN1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][NH:12][CH2:31][CH2:32]1.CS(=O)(=O)O[CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][N:18]([CH2:19][C:20]2([c:21]3[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]3)[CH2:28][CH2:29]2)[CH2:30]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11]... | COc1ccccc1N1CCNCC1.CS(=O)(=O)OCC1CCCN(CC2(c3ccc(Cl)cc3)CC2)C1 | COc1ccccc1N1CCN(CC2CCCN(CC3(c4ccc(Cl)cc4)CC3)C2)CC1 | null | null | O.C(C)#N | Heteroatom Alkylation and Arylation | Alkylation of amines | 1bf281a76f5d92191240c4561d80a265a934eb351041bae69548607f60e915b2 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | c1ccc(N2CCN(CC3CCCN(CC4(c5ccccc5)CC4)C3)CC2)cc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#7:5]-[C:4]-[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1)-[C:3] | 54.8 | [{"value": 54.8, "product": "ClC1=CC=C(C=C1)C1(CC1)CN1CC(CCC1)CN1CCN(CC1)C1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of methanesulfonic acid 1-[1-(4-chloro-phenyl)-cyclopropylmethyl]-piperidin-3-ylmethyl ester (2.94 g, 8.20 mmol) in acetonitrile (40.0 mL) at room temperature was added 1-(2-methoxy-phenyl)-piperazine (1.58 g, 8.20 mmol) followed by potassium carbonate (13.35 g, 41.0 mmol). The reaction mixture was reflux... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.C1CC[NH]CC1.c1ccccc1.C1CC1 | MsOH.HO- | O.C(C)#N | null | null | COc1ccccc1N1CCNCC1.CS(=O)(=O)OCC1CCCN(CC2(c3ccc(Cl)cc3)CC2)C1>O.C(C)#N>COc1ccccc1N1CCN(CC2CCCN(CC3(c4ccc(Cl)cc4)CC3)C2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0dbd4d7198d1482db8cfa43ccca46c06 | CCc1ccc(CCO)nc1.CS(=O)(=O)Cl.Cc1ccccc1>>CCc1ccc(CCOc2ccc(C=O)cc2)nc1 | C(C)C=1C=CC(=NC1)CCO.C(C)N(CC)CC.C1(=CC=CC=C1)C.CS(=O)(=O)Cl>>C(C)C=1C=CC(=NC1)CCOC1=CC=C(C=O)C=C1 | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][OH:9])[n:18][cH:19]1.CS(=O)(Cl)=[O:15].[c:10]1([CH3:14])[cH:11][cH:12][cH:13][cH:16][cH:17]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([CH:14]=[O:15])[cH:16][cH:17]2)[n:18][cH:19]1 | CCc1ccc(CCO)nc1.CS(=O)(=O)Cl.Cc1ccccc1 | CCc1ccc(CCOc2ccc(C=O)cc2)nc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 8135fceb97f19207e61861f22c88d41660fa03834381f75b5a09e5f0f896399b | ef7b7af1598f102ca0aae078b932ae9b72819eb1ae7b4b40e631ef4d878456f8 | c1ccc(OCCc2ccccn2)cc1 | C-S(-Cl)(=O)=[O;H0;D1;+0:1].[CH3;D1;+0:2]-[c;H0;D3;+0:3]1:[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]:1.[C:9]-[C:10]-[OH;D1;+0:11]>>[C:9]-[C:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6](-[CH;D2;+0:2]=[O;H0;D1;+0:1]):[c:7]:[c:8]:1 | null | [] | null | null | 1 | HOUR | 10 g of 5-ethyl-2-pyridine ethanol, 10.2 ml triethylamine and 75 ml toluene are added to the round bottom assembly at ambient temperature. Thereafter 6.16 ml methane sulfonyl chloride are added via dropping funnel in 1 hour. The reaction mixture is stirred at ambient temperature for 1 hour and then washed with water. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Aldehyde.Ether | c1ccccc1 | c1ccccc1 | c1ccncc1.c1ccccc1 | HCl | null | null | 1 | CCc1ccc(CCO)nc1.CS(=O)(=O)Cl.Cc1ccccc1>>CCc1ccc(CCOc2ccc(C=O)cc2)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-22689c6094034a408671349ef7f00a54 | O=Cc1ccc(OC(F)F)c(O)c1.O=[N+]([O-])c1ccc(F)c(Br)c1>>O=Cc1ccc(OC(F)F)c(Oc2ccc([N+](=O)[O-])cc2Br)c1 | BrC1=C(C=CC(=C1)[N+](=O)[O-])F.[F-].[K+].FC(OC1=C(C=C(C=O)C=C1)O)F>>FC(OC1=C(C=C(C=O)C=C1)OC1=C(C=C(C=C1)[N+](=O)[O-])Br)F | [O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]([F:9])[F:10])[c:11]([OH:12])[cH:23]1.F[c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][c:21]1[Br:22]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]([F:9])[F:10])[c:11]([O:12][c:13]2[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][c:21]2[Br:22])[cH:23]1 | O=Cc1ccc(OC(F)F)c(O)c1.O=[N+]([O-])c1ccc(F)c(Br)c1 | O=Cc1ccc(OC(F)F)c(Oc2ccc([N+](=O)[O-])cc2Br)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Br;D1;H0:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[Br;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:2]:[c:3] | null | [] | null | null | null | null | According to other embodiments, the present invention provides methods of preparing N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-methanesulfoneamide-dibenzo[b,d]furan-1-carboxamide comprising the steps of: (a) reacting 4-difluoromethoxy-3-hydroxybenzaldehyde with 2-bromo-1-fluoro-4-nitrobenzene in a first solvent com... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | null | null | null | O=Cc1ccc(OC(F)F)c(O)c1.O=[N+]([O-])c1ccc(F)c(Br)c1>>O=Cc1ccc(OC(F)F)c(Oc2ccc([N+](=O)[O-])cc2Br)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-715f96d68ecf4b60b50b33ade046d8dd | O=Cc1ccc(OC(F)F)c(O)c1.O=[N+]([O-])c1ccc(F)c(Br)c1>>O=Cc1ccc(OC(F)F)c(Oc2ccc([N+](=O)[O-])cc2Br)c1 | [F-].[K+].FC(OC1=C(C=C(C=O)C=C1)O)F.BrC1=C(C=CC(=C1)[N+](=O)[O-])F>>FC(OC1=C(C=C(C=O)C=C1)OC1=C(C=C(C=C1)[N+](=O)[O-])Br)F | [O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]([F:9])[F:10])[c:11]([OH:12])[cH:23]1.F[c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][c:21]1[Br:22]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]([F:9])[F:10])[c:11]([O:12][c:13]2[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][c:21]2[Br:22])[cH:23]1 | O=Cc1ccc(OC(F)F)c(O)c1.O=[N+]([O-])c1ccc(F)c(Br)c1 | O=Cc1ccc(OC(F)F)c(Oc2ccc([N+](=O)[O-])cc2Br)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Br;D1;H0:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[Br;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:2]:[c:3] | null | [] | null | null | null | null | In other embodiments, the present invention provides methods of preparing N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-methanesulfonamide-dibenzo[b,d]furan-1-carboxamide, as shown in FIG. 1. For example, 4-difluoromethoxy-3-hydroxybenzaldehyde may be reacted with 2-bromo-1-fluoro-4-nitrobenzene in a first solvent com... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | null | null | null | O=Cc1ccc(OC(F)F)c(O)c1.O=[N+]([O-])c1ccc(F)c(Br)c1>>O=Cc1ccc(OC(F)F)c(Oc2ccc([N+](=O)[O-])cc2Br)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0079d10c0e9d474da7f472c866bc5163 | O=C(Nc1c(Cl)cncc1Cl)c1ccc(OC(F)F)c2oc3ccc([N+](=O)[O-])cc3c12>>Nc1ccc2oc3c(OC(F)F)ccc(C(=O)Nc4c(Cl)cncc4Cl)c3c2c1 | ClC=1C=NC=C(C1NC(=O)C1=CC=C(C=2OC3=C(C21)C=C(C=C3)[N+](=O)[O-])OC(F)F)Cl.[In].ClC=1C=NC=C(C1NC(=O)C1=CC=C(C=2OC3=C(C21)C=C(C=C3)[N+](=O)[O-])OC(F)F)Cl.[In].[In]>>ClC=1C=NC=C(C1NC(=O)C1=CC=C(C=2OC3=C(C21)C=C(C=C3)N)OC(F)F)Cl | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[o:6][c:7]3[c:8]([O:9][CH:10]([F:11])[F:12])[cH:13][cH:14][c:15]([C:16](=[O:17])[NH:18][c:19]4[c:20]([Cl:21])[cH:22][n:23][cH:24][c:25]4[Cl:26])[c:27]3[c:28]2[cH:29]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[o:6][c:7]3[c:8]([O:9][CH:10]([F:11])[F:12])[cH:13][cH:14][c:15]([C:16](=[O:17])[NH... | O=C(Nc1c(Cl)cncc1Cl)c1ccc(OC(F)F)c2oc3ccc([N+](=O)[O-])cc3c12 | Nc1ccc2oc3c(OC(F)F)ccc(C(=O)Nc4c(Cl)cncc4Cl)c3c2c1 | null | null | [Cl-].[NH4+].[NH4+].[Cl-].C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(Nc1ccncc1)c1cccc2oc3ccccc3c12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 80 | CELSIUS | null | null | First, N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-aminodibenzo[b,d]furan-1-carboxamide was prepared by reacting N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide (prepared using the procedure of Example 4) with indium in ethanol and saturated ammonium chloride. To a 1 L 3-neck rou... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)oc1ccccc12.c1ccncc1 | Other | [Cl-].[NH4+].[NH4+].[Cl-].C(C)O | 80 | null | O=C(Nc1c(Cl)cncc1Cl)c1ccc(OC(F)F)c2oc3ccc([N+](=O)[O-])cc3c12>[Cl-].[NH4+].[NH4+].[Cl-].C(C)O>Nc1ccc2oc3c(OC(F)F)ccc(C(=O)Nc4c(Cl)cncc4Cl)c3c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6b0e8e1cb5944cfeb487d069970659bb | O=C(Nc1c(Cl)cncc1Cl)c1ccc(OC(F)F)c2oc3ccc([N+](=O)[O-])cc3c12>>Nc1ccc2oc3c(OC(F)F)ccc(C(=O)Nc4c(Cl)cncc4Cl)c3c2c1 | ClC=1C=NC=C(C1NC(=O)C1=CC=C(C=2OC3=C(C21)C=C(C=C3)[N+](=O)[O-])OC(F)F)Cl>>ClC=1C=NC=C(C1NC(=O)C1=CC=C(C=2OC3=C(C21)C=C(C=C3)N)OC(F)F)Cl | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[o:6][c:7]3[c:8]([O:9][CH:10]([F:11])[F:12])[cH:13][cH:14][c:15]([C:16](=[O:17])[NH:18][c:19]4[c:20]([Cl:21])[cH:22][n:23][cH:24][c:25]4[Cl:26])[c:27]3[c:28]2[cH:29]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[o:6][c:7]3[c:8]([O:9][CH:10]([F:11])[F:12])[cH:13][cH:14][c:15]([C:16](=[O:17])[NH... | O=C(Nc1c(Cl)cncc1Cl)c1ccc(OC(F)F)c2oc3ccc([N+](=O)[O-])cc3c12 | Nc1ccc2oc3c(OC(F)F)ccc(C(=O)Nc4c(Cl)cncc4Cl)c3c2c1 | null | [Ni].[Ni] | CN(C)C=O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(Nc1ccncc1)c1cccc2oc3ccccc3c12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 91.3 | [{"value": 91.3, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Second, N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-aminodibenzo[b,d]furan-1-carboxamide was prepared by reacting N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide (prepared using the procedure of Example 4) with Raney Nickel. In particular, to a 500 mL pressure vessel was added N′... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)oc1ccccc12.c1ccncc1 | Other | [Ni].[Ni].CN(C)C=O | null | null | O=C(Nc1c(Cl)cncc1Cl)c1ccc(OC(F)F)c2oc3ccc([N+](=O)[O-])cc3c12>[Ni].[Ni].CN(C)C=O>Nc1ccc2oc3c(OC(F)F)ccc(C(=O)Nc4c(Cl)cncc4Cl)c3c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-824f639efe49499785302908ee443f3a | O=C(Nc1c(Cl)cncc1Cl)c1ccc(OC(F)F)c2oc3ccc([N+](=O)[O-])cc3c12>>Nc1ccc2oc3c(OC(F)F)ccc(C(=O)Nc4c(Cl)cncc4Cl)c3c2c1 | [Cl-].[NH4+].ClC=1C=NC=C(C1NC(=O)C1=CC=C(C=2OC3=C(C21)C=C(C=C3)[N+](=O)[O-])OC(F)F)Cl>>ClC=1C=NC=C(C1NC(=O)C1=CC=C(C=2OC3=C(C21)C=C(C=C3)N)OC(F)F)Cl | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[o:6][c:7]3[c:8]([O:9][CH:10]([F:11])[F:12])[cH:13][cH:14][c:15]([C:16](=[O:17])[NH:18][c:19]4[c:20]([Cl:21])[cH:22][n:23][cH:24][c:25]4[Cl:26])[c:27]3[c:28]2[cH:29]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[o:6][c:7]3[c:8]([O:9][CH:10]([F:11])[F:12])[cH:13][cH:14][c:15]([C:16](=[O:17])[NH... | O=C(Nc1c(Cl)cncc1Cl)c1ccc(OC(F)F)c2oc3ccc([N+](=O)[O-])cc3c12 | Nc1ccc2oc3c(OC(F)F)ccc(C(=O)Nc4c(Cl)cncc4Cl)c3c2c1 | null | [Zn].[Zn] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(Nc1ccncc1)c1cccc2oc3ccccc3c12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 79.4 | [{"value": 79.4, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | Third, N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-aminodibenzo[b,d]furan-1-carboxamide was prepared by reacting N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide (prepared using the procedure of Example 4) with zinc. In particular, to a 250 mL 2-necked round bottom flask was added... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)oc1ccccc12.c1ccncc1 | Other | [Zn].[Zn].C(C)O | 95 | null | O=C(Nc1c(Cl)cncc1Cl)c1ccc(OC(F)F)c2oc3ccc([N+](=O)[O-])cc3c12>[Zn].[Zn].C(C)O>Nc1ccc2oc3c(OC(F)F)ccc(C(=O)Nc4c(Cl)cncc4Cl)c3c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e144463b449443ad8ea96c41bd4203b8 | O=C(Nc1c(Cl)cncc1Cl)c1ccc(OC(F)F)c2oc3ccc([N+](=O)[O-])cc3c12>>Nc1ccc2oc3c(OC(F)F)ccc(C(=O)Nc4c(Cl)cncc4Cl)c3c2c1 | ClC=1C=NC=C(C1NC(=O)C1=CC=C(C=2OC3=C(C21)C=C(C=C3)[N+](=O)[O-])OC(F)F)Cl.ClC=1C=NC=C(C1NC(=O)C1=CC=C(C=2OC3=C(C21)C=C(C=C3)[N+](=O)[O-])OC(F)F)Cl.Cl.[BH4-].[Na+].[BH4-].[Na+]>>ClC=1C=NC=C(C1NC(=O)C1=CC=C(C=2OC3=C(C21)C=C(C=C3)N)OC(F)F)Cl | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[o:6][c:7]3[c:8]([O:9][CH:10]([F:11])[F:12])[cH:13][cH:14][c:15]([C:16](=[O:17])[NH:18][c:19]4[c:20]([Cl:21])[cH:22][n:23][cH:24][c:25]4[Cl:26])[c:27]3[c:28]2[cH:29]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[o:6][c:7]3[c:8]([O:9][CH:10]([F:11])[F:12])[cH:13][cH:14][c:15]([C:16](=[O:17])[NH... | O=C(Nc1c(Cl)cncc1Cl)c1ccc(OC(F)F)c2oc3ccc([N+](=O)[O-])cc3c12 | Nc1ccc2oc3c(OC(F)F)ccc(C(=O)Nc4c(Cl)cncc4Cl)c3c2c1 | null | [Pd].[Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(Nc1ccncc1)c1cccc2oc3ccccc3c12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 7.5 | CELSIUS | null | null | Fourth, N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-aminodibenzo[b,d]furan-1-carboxamide was prepared by reacting N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-nitro-dibenzo[b,d]furan-1-carboxamide (prepared using the procedure of Example 4) with sodium borohydride in methanol and palladium on carbon (50% wet with ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)oc1ccccc12.c1ccncc1 | Other | [Pd].[Pd].CO | 7.5 | null | O=C(Nc1c(Cl)cncc1Cl)c1ccc(OC(F)F)c2oc3ccc([N+](=O)[O-])cc3c12>[Pd].[Pd].CO>Nc1ccc2oc3c(OC(F)F)ccc(C(=O)Nc4c(Cl)cncc4Cl)c3c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d32e44336ab474fa7ed89bdaf146243 | COc1ccccc1Cl.O=C(Cl)CCCl>>COc1cc2c(cc1Cl)C(=O)CC2 | S(O)(O)(=O)=O.ClC1=C(C=CC=C1)OC.ClCCC(=O)Cl.[Al+3].[Cl-].[Cl-].[Cl-]>>ClC1=C(C=C2CCC(C2=C1)=O)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[Cl:9].Cl[C:10](=[O:11])[CH2:12][CH2:13]Cl>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[Cl:9])[C:10](=[O:11])[CH2:12][CH2:13]2 | COc1ccccc1Cl.O=C(Cl)CCCl | COc1cc2c(cc1Cl)C(=O)CC2 | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 54e4063f482a505c1566def1ae70d791f57b6a30eeb317d048d2c7802bd26423 | 4891bfec14a44c572847b13e296d05d3abe17c47adfe6f321080d329be8991f3 | O=C1CCc2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2]-[C;H0;D3;+0:3](-Cl)=[O;D1;H0:4].[c:5]1:[c:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[c:9]:[c:10]:1>>[O;D1;H0:4]=[C;H0;D3;+0:3]1-[C:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:7]2:[c:6]:[c:5]:[c:10]:[c:9]:[c;H0;D3;+0:8]:2-1 | null | [] | 100 | CELSIUS | 30 | MINUTE | To a solution of 1-chloro-2-methoxybenzene (12.8 mL, 100 mmol) and 3-chloropropanoyl chloride (10.5 mL, 110 mmol) in CH2Cl2 (100 mL) at 0° C. was added AlCl3 (14.6 g, 110 mmol) portionwise during about 1 minute. After 30 minutes, sulfuric acid (300 mL) was poured slowly into the reaction mixture during about 3 minutes.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary halide | Ketone | c1ccccc1 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HCl | C(Cl)Cl | 100 | 0.5 | COc1ccccc1Cl.O=C(Cl)CCCl>C(Cl)Cl>COc1cc2c(cc1Cl)C(=O)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-450375708e3e4b9e984a1b52160e2f1e | CCOC(=O)C#N.COc1cc2c(cc1Cl)C(=O)CC2>>CCOC(=O)C1Cc2cc(OC)c(Cl)cc2C1=O | C(#N)C(=O)OCC.ClC1=C(C=C2CCC(C2=C1)=O)OC.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>ClC1=C(C=C2CC(C(C2=C1)=O)C(=O)OCC)OC | N#C[C:4]([O:3][CH2:2][CH3:1])=[O:5].[CH2:6]1[CH2:7][c:8]2[cH:9][c:10]([O:11][CH3:12])[c:13]([Cl:14])[cH:15][c:16]2[C:17]1=[O:18]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][c:8]2[cH:9][c:10]([O:11][CH3:12])[c:13]([Cl:14])[cH:15][c:16]2[C:17]1=[O:18] | CCOC(=O)C#N.COc1cc2c(cc1Cl)C(=O)CC2 | CCOC(=O)C1Cc2cc(OC)c(Cl)cc2C1=O | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 0f8301238f55311e0fc642450d793fb0499dfa9b94fae7471e9160ef412b7dd2 | ea62efa90ef3cfb13125a23e62e9e1787aa2a0b0ee48c8a61b3326a3bda24134 | O=C1CCc2ccccc21 | N#C-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[O;D1;H0:5]=[C:6]1-[CH2;D2;+0:7]-[C:8]-[c:9]:[c:10]-1>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:7]1-[C:8]-[c:9]:[c:10]-[C:6]-1=[O;D1;H0:5] | null | [] | -78 | CELSIUS | null | null | To a solution of 6-chloro-5-methoxyindan-1-one (27.6 g, 141 mmol) in THF (630 mL) at −78° C. was added a 1.0M solution of lithium bis(trimethylsilyl)amide in THF (309 mL, 309 mmol) and then the solution was slowly warmed to ca −50° C. during 1 hour. After re-cooling to −78° C., ethyl cyanoformate (21.3 mL, 216 mmol) wa... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitrile | Ketone.Ester | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | Other | C1CCOC1 | -78 | null | CCOC(=O)C#N.COc1cc2c(cc1Cl)C(=O)CC2>C1CCOC1>CCOC(=O)C1Cc2cc(OC)c(Cl)cc2C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-92195910957b4b4d927968fab15171cd | CCOC(=O)C1Cc2cc(OC)c(Cl)cc2C1=O.FCCBr>>COc1cc2c(cc1Cl)C(=O)C(CCF)C2 | [OH-].[Na+].ClC1=C(C=C2CC(C(C2=C1)=O)C(=O)OCC)OC.C(=O)([O-])[O-].[K+].[K+].BrCCF>>ClC1=C(C=C2CC(C(C2=C1)=O)CCF)OC | CCOC(=O)[CH:12]1[C:10](=[O:11])[c:6]2[c:5]([cH:4][c:3]([O:2][CH3:1])[c:8]([Cl:9])[cH:7]2)[CH2:16]1.Br[CH2:13][CH2:14][F:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[Cl:9])[C:10](=[O:11])[CH:12]([CH2:13][CH2:14][F:15])[CH2:16]2 | CCOC(=O)C1Cc2cc(OC)c(Cl)cc2C1=O.FCCBr | COc1cc2c(cc1Cl)C(=O)C(CCF)C2 | null | null | O.CC(=O)N(C)C | C-C Coupling | OtherReaction | eaf2c6345598db4bafc43dfd5960e2c4d5dab87b5f467fecb90ec97d72862f5e | ce7b75becdbf06d1618bfce7bcc7e9c53441b0656e1b7c7325fe306df5895906 | O=C1CCc2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[F;D1;H0:3].C-C-O-C(=O)-[CH;D3;+0:4]1-[C:5]-[c:6]:[c:7]-[C:8]-1=[O;D1;H0:9]>>[F;D1;H0:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:4]1-[C:5]-[c:6]:[c:7]-[C:8]-1=[O;D1;H0:9] | null | [] | 65 | CELSIUS | 2 | HOUR | To a solution of ethyl 6-chloro-5-methoxy-1-oxoindane-2-carboxylate (crude product from the preceding step, ˜141 mmol) in anhydrous dimethylacetamide (540 mL) was added K2CO3 (39 g, 282 mmol), KI (46.8 g, 282 mmol) and 1-bromo-2-fluoroethane (13.5 mL, 183 mmol) and the mixture was stirred and heated at 65° C. for 6 hou... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ester | Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | HBr | O.CC(=O)N(C)C | 65 | 2 | CCOC(=O)C1Cc2cc(OC)c(Cl)cc2C1=O.FCCBr>O.CC(=O)N(C)C>COc1cc2c(cc1Cl)C(=O)C(CCF)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a422c20f5fe84af7b5f05ec4d1685d87 | C=CC(C)=O.COc1cc2c(cc1Cl)C(=O)C(CCF)C2>>COc1cc2c(cc1Cl)C(=O)C(CCF)(CCC(C)=O)C2 | [OH-].[K+].C(=C)C(=O)C.ClC1=C(C=C2CC(C(C2=C1)=O)CCF)OC.C=C[C@H]1C[N+]2(CC[C@H]1C[C@@H]2[C@H](C3=CC=NC4=CC=CC=C34)O)CC5=CC=C(C=C5)C(F)(F)F.[Br-]>>ClC1=C(C=C2CC(C(C2=C1)=O)(CCC(C)=O)CCF)OC | [CH2:16]=[CH:17][C:18]([CH3:19])=[O:20].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[Cl:9])[C:10](=[O:11])[CH:12]([CH2:13][CH2:14][F:15])[CH2:21]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[Cl:9])[C:10](=[O:11])[C:12]([CH2:13][CH2:14][F:15])([CH2:16][CH2:17][C:18]([CH3:19])=[O:20])[CH2:21]2 | C=CC(C)=O.COc1cc2c(cc1Cl)C(=O)C(CCF)C2 | COc1cc2c(cc1Cl)C(=O)C(CCF)(CCC(C)=O)C2 | null | null | ClCCl.C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | c504c0d32586144b6874498db3cc99d4d5bb675e1b2e725385a0386d3f14ac05 | 68a0b2d4768a64505cf15a6dd6bbd75216aef3c50fb86aff9b39341b3e49f06d | O=C1CCc2ccccc21 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:4]=[CH2;D1;+0:5].[C:6]-[C:7]-[CH;D3;+0:8]1-[C:9]-[c:10]:[c:11]-[C:12]-1=[O;D1;H0:13]>>[C:6]-[C:7]-[C;H0;D4;+0:8]1(-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[C:2](-[C;D1;H3:1])=[O;D1;H0:3])-[C:9]-[c:10]:[c:11]-[C:12]-1=[O;D1;H0:13] | null | [] | null | null | 30 | MINUTE | To a solution of 6-chloro-2-(2-fluoroethyl)-5-methoxyindan-1-one (34 g, 140 mmol) in toluene (1500 mL) was added N-[4-(trifluoromethyl)benzyl]cinchoninium bromide (13 g, 24 mmol) and the mixture was stirred at room temperature for 30 minutes. After cooling to 0° C., methyl vinyl ketone (20 mL, 240 mmol) was added follo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Vinyl | Ketone.Ketone | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | null | ClCCl.C1(=CC=CC=C1)C | null | 0.5 | C=CC(C)=O.COc1cc2c(cc1Cl)C(=O)C(CCF)C2>ClCCl.C1(=CC=CC=C1)C>COc1cc2c(cc1Cl)C(=O)C(CCF)(CCC(C)=O)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6fc3ff70fc1145e6965aa98f5831f3c5 | COc1cc2c(cc1Cl)C(=O)C(CCF)(CCC(C)=O)C2>>COc1cc2c(cc1Cl)C1=CC(=O)CCC1(CCF)C2 | ClC1=C(C=C2CC(C(C2=C1)=O)(CCC(C)=O)CCF)OC.C(C)(=O)O.N1CCCC1>>ClC=1C=C2C3=CC(CCC3(CC2=CC1OC)CCF)=O | O=[C:10]1[c:6]2[c:5]([cH:4][c:3]([O:2][CH3:1])[c:8]([Cl:9])[cH:7]2)[CH2:20][C:16]1([CH2:15][CH2:14][C:12]([CH3:11])=[O:13])[CH2:17][CH2:18][F:19]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[Cl:9])[C:10]1=[CH:11][C:12](=[O:13])[CH2:14][CH2:15][C:16]1([CH2:17][CH2:18][F:19])[CH2:20]2 | COc1cc2c(cc1Cl)C(=O)C(CCF)(CCC(C)=O)C2 | COc1cc2c(cc1Cl)C1=CC(=O)CCC1(CCF)C2 | null | null | C1(=CC=CC=C1)C.CCOC(=O)C | Functional Group Interconversion | OtherReaction | 85ff0aa8be631f96366b93c0f2ba199404913ad074e95e1352514ec4827258a9 | b7bc018679e3f4c5a72b49c90c858cc3bcb4db12dedb0216b468af50ef8a00a3 | O=C1C=C2c3ccccc3CC2CC1 | O=[C;H0;D3;+0:1]1-[c:2](:[c:3]):[c:4]-[C:5]-[C:6]-1(-[C:7])-[C:8]-[C:9]-[C:10](-[CH3;D1;+0:11])=[O;D1;H0:12]>>[C:7]-[C:6]12-[C:8]-[C:9]-[C:10](=[O;D1;H0:12])-[CH;D2;+0:11]=[C;H0;D3;+0:1]-1-[c:2](:[c:3]):[c:4]-[C:5]-2 | null | [] | 95 | CELSIUS | null | null | To a solution of 6-chloro-2-(2-fluoroethyl)-5-methoxy-2-(3-oxobutyl)indan-1-one (32 g, 102 mmol) in toluene (1000 mL) were added acetic acid (7.0 mL, 120 mmol) and pyrrolidine (10 mL, 120 mmol) and the solution was heated at 95° C. for 2 hours. After cooling to room temperature, the reaction mixture was diluted with Et... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | c1ccc2c(c1)CCC2 | C1=C2c3ccccc3CC2CCC1 | C1=C2c3ccccc3CC2CCC1 | HO- | C1(=CC=CC=C1)C.CCOC(=O)C | 95 | null | COc1cc2c(cc1Cl)C(=O)C(CCF)(CCC(C)=O)C2>C1(=CC=CC=C1)C.CCOC(=O)C>COc1cc2c(cc1Cl)C1=CC(=O)CCC1(CCF)C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bba0d7e5822746829124c9cba0e9bdee | O=C1C(C(F)(F)F)=C2c3cc(Cl)c4[nH]nnc4c3CC23CCC1C3>>O=C1C(C(F)(F)F)=C2c3ccc4[nH]nnc4c3CC23CCC1C3 | ClC1=CC=2C=3C4(CC2C=2N=NNC21)CCC(C(C3C(F)(F)F)=O)C4>>FC(C=1C(C2CCC3(C1C=1C=CC4=C(N=NN4)C1C3)C2)=O)(F)F | Cl[c:11]1[cH:10][c:9]2[c:17]([c:16]3[c:12]1[nH:13][n:14][n:15]3)[CH2:18][C:19]13[C:8]2=[C:3]([C:4]([F:5])([F:6])[F:7])[C:2](=[O:1])[CH:22]([CH2:21][CH2:20]1)[CH2:23]3>>[O:1]=[C:2]1[C:3]([C:4]([F:5])([F:6])[F:7])=[C:8]2[c:9]3[cH:10][cH:11][c:12]4[nH:13][n:14][n:15][c:16]4[c:17]3[CH2:18][C:19]23[CH2:20][CH2:21][CH:22]1[C... | O=C1C(C(F)(F)F)=C2c3cc(Cl)c4[nH]nnc4c3CC23CCC1C3 | O=C1C(C(F)(F)F)=C2c3ccc4[nH]nnc4c3CC23CCC1C3 | null | [OH-].[OH-].[Pd+2].[Pd].[OH-].[OH-].[Pd+2].[Pd] | ClCCl.CN(C)C=O | Functional Group Interconversion | Aromatic dehalogenation | 9e3085e60c60726e4eccbf2b3b9bcf4e8944c9db2a05e9b4833fce06217a9387 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=C1C=C2c3ccc4[nH]nnc4c3CC23CCC1C3 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](:[c:4]:[c:5]2:[#7;a:6]:[#7;a:7]:[#7;a:8]:[c:9]:2:1)-[C:10]=[C:11]>>[C:11]=[C:10]-[c:3]1:[c:2]:[cH;D2;+0:1]:[c:9]2:[#7;a:8]:[#7;a:7]:[#7;a:6]:[c:5]:2:[c:4]:1 | null | [] | null | null | 29 | HOUR | To a solution of 4-chloro-6-(trifluoromethyl)-3,9,10,11-tetrahydro-8,10a-methanocyclohepta-[1,2]indeno[4,5-d][1,2,3]triazol-7(8H)-one (2.3 g, crude product from the preceding step, ˜6.1 mmol) in DMF (230 mL) were added 20% Pd(OH)2 on carbon (1 g) and 5% palladium on calcium carbonate (1 g) and the mixture was hydrogena... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | C1=C2c3ccc4[nH]nnc4c3CC23CCC(C1)C3 | C1=C2c3ccc4[nH]nnc4c3CC23CCC(C1)C3 | C1=C2c3ccc4[nH]nnc4c3CC23CCC(C1)C3 | Other | [OH-].[OH-].[Pd+2].[Pd].[OH-].[OH-].[Pd+2].[Pd].ClCCl.CN(C)C=O | null | 29 | O=C1C(C(F)(F)F)=C2c3cc(Cl)c4[nH]nnc4c3CC23CCC1C3>[OH-].[OH-].[Pd+2].[Pd].[OH-].[OH-].[Pd+2].[Pd].ClCCl.CN(C)C=O>O=C1C(C(F)(F)F)=C2c3ccc4[nH]nnc4c3CC23CCC1C3 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee17a8ee917b4310acf2748350a329c2 | O=C1C(C(F)(F)F)=C2c3ccc4[nH]nnc4c3CC23CCC1C3>>O=C1C(C(F)(F)F)=C2c3ccc4[nH]nnc4c3C[C@@]23CC[C@@H]1C3 | FC(C=1C(C2CCC3(C1C=1C=CC4=C(N=NN4)C1C3)C2)=O)(F)F>>FC(C=1C([C@@H]2CC[C@]3(C1C=1C=CC4=C(N=NN4)C1C3)C2)=O)(F)F | [O:1]=[C:2]1[C:3]([C:4]([F:5])([F:6])[F:7])=[C:8]2[c:9]3[cH:10][cH:11][c:12]4[nH:13][n:14][n:15][c:16]4[c:17]3[CH2:18][C:19]23[CH2:20][CH2:21][CH:22]1[CH2:23]3>>[O:1]=[C:2]1[C:3]([C:4]([F:5])([F:6])[F:7])=[C:8]2[c:9]3[cH:10][cH:11][c:12]4[nH:13][n:14][n:15][c:16]4[c:17]3[CH2:18][C@@:19]23[CH2:20][CH2:21][C@@H:22]1[CH2:... | O=C1C(C(F)(F)F)=C2c3ccc4[nH]nnc4c3CC23CCC1C3 | O=C1C(C(F)(F)F)=C2c3ccc4[nH]nnc4c3C[C@@]23CC[C@@H]1C3 | null | null | C(C)O.CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1C=C2c3ccc4[nH]nnc4c3C[C@@]23CC[C@@H]1C3 | null | null | [] | null | null | null | null | 6-(trifluoromethyl)-3,9,10,11-tetrahydro-8,10a-methanocyclohepta-[1,2]indeno[4,5-d][1,2,3]triazol-7(8H)-one [1.8 g, (8R,10aS): (8S,10aR) enantiomeric ratio ˜2:1] was dissolved in 1/1 ethanol/methanol (130 mL) and resolved by chiral HPLC on a 2.0×25 cm Daicel Chiralcel OJ column (4 mL injections, elution with 35% EtOH:H... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1=C2c3ccc4[nH]nnc4c3C[C@@]23CC[C@@H](C1)C3 | null | C(C)O.CO | null | null | O=C1C(C(F)(F)F)=C2c3ccc4[nH]nnc4c3CC23CCC1C3>C(C)O.CO>O=C1C(C(F)(F)F)=C2c3ccc4[nH]nnc4c3C[C@@]23CC[C@@H]1C3 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c6a5076affd492bb306e26b8339b3a6 | CSCCO.O=C(O)CCl>>CSCCOCC(=O)O | CSCCO.[H-].[Na+].ClCC(=O)O.Cl.[Cl-].[Na+]>>CSCCOCC(=O)O | [CH3:1][S:2][CH2:3][CH2:4][OH:5].Cl[CH2:6][C:7](=[O:8])[OH:9]>>[CH3:1][S:2][CH2:3][CH2:4][O:5][CH2:6][C:7](=[O:8])[OH:9] | CSCCO.O=C(O)CCl | CSCCOCC(=O)O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | null | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4] | 69.5 | [{"value": 69.0, "product": "CSCCOCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.5, "product": "CSCCOCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 2-methylthioethanol (10.0 g, 0.108 mol) in dry tetrahydrofuran (25 ml) was added dropwise, over 30 min, to a suspension of sodium hydride (9.54 g of a 60% dispersion in mineral oil, 0.238 mol, washed twice with hexane) in dry tetrahydrofuran (250 ml) at 22° C. After 30 min, a solution of chloroacetic acid... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | null | HCl | O1CCCC1 | null | 0.5 | CSCCO.O=C(O)CCl>O1CCCC1>CSCCOCC(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ecbd4d63304a4295a8e3af1f88159dc3 | CCOC(=O)C(=O)OCC.CCOC(=O)COCc1ccccc1.CSCCOCC(=N)N>>CCOC(=O)c1nc(COCCSC)[nH]c(=O)c1OCc1ccccc1 | C(C(=O)OCC)(=O)OCC.C(C1=CC=CC=C1)OCC(=O)OCC.[H-].[Na+].Cl.CSCCOCC(=N)N.[O-]CC.[Na+]>>C(C1=CC=CC=C1)OC1=C(N=C(NC1=O)COCCSC)C(=O)OCC | CCO[C:6](=O)[C:4]([O:3][CH2:2][CH3:1])=[O:5].CCO[C:16](=[O:17])[CH2:18][O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.[NH2:7][C:8]([CH2:9][O:10][CH2:11][CH2:12][S:13][CH3:14])=[NH:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([CH2:9][O:10][CH2:11][CH2:12][S:13][CH3:14])[nH:15][c:16](=[O:17])[c:18]1[O... | CCOC(=O)C(=O)OCC.CCOC(=O)COCc1ccccc1.CSCCOCC(=N)N | CCOC(=O)c1nc(COCCSC)[nH]c(=O)c1OCc1ccccc1 | null | null | O1CCCC1.C(C)(=O)O.C(C)O | Aromatic Heterocycle Formation | OtherReaction | 46371e328b8a1712f756c7bcf70de676b2e5cf18d81f22c713bd44fafb3129e2 | ea76cf999399ad97517ace00236aa5bf5d606c07e4032211096f3bda6a8ec4ae | O=c1[nH]cncc1OCc1ccccc1 | C-C-O-[C;H0;D3;+0:1](=O)-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].C-C-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[#8:9]-[C:10].[#8:11]-[C:12]-[C;H0;D3;+0:13](-[NH2;D1;+0:14])=[NH;D1;+0:15]>>[#8:11]-[C:12]-[c;H0;D3;+0:13]1:[n;H0;D2;+0:14]:[c;H0;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5]):[c;H0;D3;+0:8](-[#8:9]-[C:10]):[c;H0;D... | 10.1 | [{"value": 10.0, "product": "C(C1=CC=CC=C1)OC1=C(N=C(NC1=O)COCCSC)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.1, "product": "C(C1=CC=CC=C1)OC1=C(N=C(NC1=O)COCCSC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 22 | CELSIUS | 18 | HOUR | Diethyl oxalate (2.77 g, 19.0 mmol) and ethyl benzyloxyacetate (3.69 g, 19.0 mmol) in dry tetrahydrofuran (30 ml) were treated at 22° C. with sodium hydride (0.83 g of a 60% dispersion in mineral oil, 20.9 mmol) followed by ethanol (10 μl) and the resulting mixture was stirred at 22° C. for 18 h. The tetrahydrofuran wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ether.Primary amine | Ester.Ether | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | O1CCCC1.C(C)(=O)O.C(C)O | 22 | 18 | CCOC(=O)C(=O)OCC.CCOC(=O)COCc1ccccc1.CSCCOCC(=N)N>O1CCCC1.C(C)(=O)O.C(C)O>CCOC(=O)c1nc(COCCSC)[nH]c(=O)c1OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a9e2ff3243384a1da476218e33659040 | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2>>O=C(O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2 | Cl.C(C)(=O)OCC.C(C1=CC=CC=C1)OC1=C(N=C2COCCN2C1=O)C(=O)OCC.[OH-].[Na+]>>C(C1=CC=CC=C1)OC1=C(N=C2COCCN2C1=O)C(=O)O | CC[O:3][C:2](=[O:1])[c:4]1[n:5][c:6]2[n:7]([c:8](=[O:9])[c:10]1[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19][CH2:20][O:21][CH2:22]2>>[O:1]=[C:2]([OH:3])[c:4]1[n:5][c:6]2[n:7]([c:8](=[O:9])[c:10]1[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[CH2:19][CH2:20][O:21][CH2:22]2 | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2 | O=C(O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1c(OCc2ccccc2)cnc2n1CCOC2 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 96 | [{"value": 96.0, "product": "C(C1=CC=CC=C1)OC1=C(N=C2COCCN2C1=O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 30 | MINUTE | A solution of intermediate 6, ethyl 3-(benzyloxy)-4-oxo-4,6,7,9-tetrahydropyrimido[2, 1-c][1,4]oxazine-2-carboxylate (0.300 g, 0.91 mmol) in ethanol (10 ml) was treated with 3 ml (3.0 mmol) of 1 N sodium hydroxide and stirred at 25° C. for 30 min. The solution was then acidified with 1 N hydrochloric acid, extracted wi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cnc2n(c1)CCOC2 | Other | C(C)O | 25 | 0.5 | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2>C(C)O>O=C(O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-882afcb75c084747b453be8718594113 | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2>>CCOC(=O)c1nc2n(c(=O)c1O)CCOC2 | [H][H].C(C1=CC=CC=C1)OC1=C(N=C2COCCN2C1=O)C(=O)OCC>>OC1=C(N=C2COCCN2C1=O)C(=O)OCC | c1ccc(C[O:13][c:12]2[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:7][c:8]3[n:9]([c:10]2=[O:11])[CH2:14][CH2:15][O:16][CH2:17]3)cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]2[n:9]([c:10](=[O:11])[c:12]1[OH:13])[CH2:14][CH2:15][O:16][CH2:17]2 | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2 | CCOC(=O)c1nc2n(c(=O)c1O)CCOC2 | null | [Pd] | C(C)(=O)OCC.C(C)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=c1ccnc2n1CCOC2 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7](:[c:8](=[O;D1;H0:9]):[c:10]:1-[O;H0;D2;+0:11]-C-c1:c:c:c:c:c:1)-[C:12]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7](:[c:8](=[O;D1;H0:9]):[c:10]:1-[OH;D1;+0:11])-[C:12] | 94 | [{"value": 94.0, "product": "OC1=C(N=C2COCCN2C1=O)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.3, "product": "OC1=C(N=C2COCCN2C1=O)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of intermediate 6, ethyl 3-benzyloxy-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylate, (0.236 g, 0.714 mmol) in a mixture of ethyl acetate (60 ml) and ethanol (20 ml) was treated with 1 atm of hydrogen at 25° C. over 10% palladium on activated carbon (0.10 g) for 2.5 h to give 0.160 g (94% y... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1cnc2n(c1)CCOC2 | Other | [Pd].C(C)(=O)OCC.C(C)O | null | null | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2>[Pd].C(C)(=O)OCC.C(C)O>CCOC(=O)c1nc2n(c(=O)c1O)CCOC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc1b33f1b3d544009377fcc2ac6b142b | CC(Br)C(=O)O.CSCCO>>CSCCOC(C)C(=O)O | CSCCO.[H-].[Na+].BrC(C(=O)O)C>>CSCCOC(C(=O)O)C | Br[CH:6]([CH3:7])[C:8](=[O:9])[OH:10].[CH3:1][S:2][CH2:3][CH2:4][OH:5]>>[CH3:1][S:2][CH2:3][CH2:4][O:5][CH:6]([CH3:7])[C:8](=[O:9])[OH:10] | CC(Br)C(=O)O.CSCCO | CSCCOC(C)C(=O)O | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | fda3169c328a6f91cb846e38fa3ac4b3ce257430d2fcd0b686a69a7f68177524 | 94d87fb4ea980bbbd72819243a58e7529341c8cedb8a1df6d3eb0aee97042951 | null | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[O;D1;H1:5] | 78 | [{"value": 78.0, "product": "CSCCOC(C(=O)O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.9, "product": "CSCCOC(C(=O)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Addition of 2-methylthioethanol (10.0 g, 0.108 mol) to sodium hydride (9.54 g of a 60% dispersion in mineral oil, 0.238 mol, washed twice with hexane) followed by reaction with 2-bromopropionic acid (16.6 g, 0.108 mol) gave 13.81 g (78% yield) of the title compound as a clear oil; bp 80-90° C./0.2 torr (bulb to bulb di... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary alcohol | Ether | null | null | null | HBr | null | null | null | CC(Br)C(=O)O.CSCCO>>CSCCOC(C)C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e961f4262fe4f58bd3081ac9c1db85e | CSCCOC(C)C(=O)O>>COC(=O)C(C)OCCSC | CSCCOC(C(=O)O)C.C(C(=O)Cl)(=O)Cl>>CSCCOC(C(=O)OC)C | [OH:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][CH2:8][CH2:9][S:10][CH3:11]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][CH2:8][CH2:9][S:10][CH3:11] | CSCCOC(C)C(=O)O | COC(=O)C(C)OCCSC | null | null | CO | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | null | [C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4]>>[C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[C;D1;H3:5] | 96 | [{"value": 96.0, "product": "CSCCOC(C(=O)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of intermediate 9, 2-(2-(methylthio)ethoxy)propanoic acid, (13.70 g, 0.083 mol) with oxalyl chloride followed by reaction with methanol gave 14.27 g (96% yield) of the title ester as a clear oil; bp 55-60° C./0.3 torr (bulb to bulb distillation, air bath temperature). 1HNMR 400 MHz (CDCl3) δ ppm: 1.42 (3H, d, ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | null | Other | CO | null | null | CSCCOC(C)C(=O)O>CO>COC(=O)C(C)OCCSC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-609db6aad0224a97bf8b94d9ef29a8ca | CCOC(=O)C(=O)OCC.CCOC(=O)COCc1ccccc1.CSCCOC(C)C(=N)N>>CCOC(=O)c1nc(C(C)OCCSC)[nH]c(=O)c1OCc1ccccc1 | C(C(=O)OCC)(=O)OCC.C(C1=CC=CC=C1)OCC(=O)OCC.[H-].[Na+].Cl.CSCCOC(C(=N)N)C.[O-]CC.[Na+]>>C(C1=CC=CC=C1)OC1=C(N=C(NC1=O)C(C)OCCSC)C(=O)OCC | CCO[C:6](=O)[C:4]([O:3][CH2:2][CH3:1])=[O:5].CCO[C:17](=[O:18])[CH2:19][O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.[NH2:7][C:8]([CH:9]([CH3:10])[O:11][CH2:12][CH2:13][S:14][CH3:15])=[NH:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([CH:9]([CH3:10])[O:11][CH2:12][CH2:13][S:14][CH3:15])[nH:16][c:17]... | CCOC(=O)C(=O)OCC.CCOC(=O)COCc1ccccc1.CSCCOC(C)C(=N)N | CCOC(=O)c1nc(C(C)OCCSC)[nH]c(=O)c1OCc1ccccc1 | null | null | O1CCCC1.C(C)O | Aromatic Heterocycle Formation | OtherReaction | 46371e328b8a1712f756c7bcf70de676b2e5cf18d81f22c713bd44fafb3129e2 | ea76cf999399ad97517ace00236aa5bf5d606c07e4032211096f3bda6a8ec4ae | O=c1[nH]cncc1OCc1ccccc1 | C-C-O-[C;H0;D3;+0:1](=O)-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].C-C-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[#8:9]-[C:10].[#8:11]-[C:12](-[C;D1;H3:13])-[C;H0;D3;+0:14](-[NH2;D1;+0:15])=[NH;D1;+0:16]>>[#8:11]-[C:12](-[C;D1;H3:13])-[c;H0;D3;+0:14]1:[n;H0;D2;+0:15]:[c;H0;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5]):[c;H0;D3... | 15.1 | [{"value": 15.0, "product": "C(C1=CC=CC=C1)OC1=C(N=C(NC1=O)C(C)OCCSC)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.1, "product": "C(C1=CC=CC=C1)OC1=C(N=C(NC1=O)C(C)OCCSC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Diethyl oxalate (5.66 g, 38.7 mmol) and ethyl benzyloxyacetate (7.52 g, 38.7 mmol) in dry tetrahydrofuran (60 ml) were treated at 22° C. with sodium hydride (1.70 g of a 60% dispersion in mineral oil, 42.5 mmol) and the condensation product was reacted with a mixture of intermediate 11, 2-(2-(methylthio)ethoxy)propanam... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ether.Primary amine | Ester.Ether | null | c1cncnc1 | c1cncnc1.c1ccccc1 | HO- | O1CCCC1.C(C)O | null | null | CCOC(=O)C(=O)OCC.CCOC(=O)COCc1ccccc1.CSCCOC(C)C(=N)N>O1CCCC1.C(C)O>CCOC(=O)c1nc(C(C)OCCSC)[nH]c(=O)c1OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f49ea71d7161479a8a4f4fd180901276 | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2C>>CCOC(=O)c1nc2n(c(=O)c1O)CCOC2C | C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)C)C(=O)OCC.[H][H]>>OC1=C(N=C2C(OCCN2C1=O)C)C(=O)OCC | c1ccc(C[O:13][c:12]2[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:7][c:8]3[n:9]([c:10]2=[O:11])[CH2:14][CH2:15][O:16][CH:17]3[CH3:18])cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]2[n:9]([c:10](=[O:11])[c:12]1[OH:13])[CH2:14][CH2:15][O:16][CH:17]2[CH3:18] | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2C | CCOC(=O)c1nc2n(c(=O)c1O)CCOC2C | null | [Pd] | C(C)(=O)OCC.C(C)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=c1ccnc2n1CCOC2 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7](:[c:8](=[O;D1;H0:9]):[c:10]:1-[O;H0;D2;+0:11]-C-c1:c:c:c:c:c:1)-[C:12]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7](:[c:8](=[O;D1;H0:9]):[c:10]:1-[OH;D1;+0:11])-[C:12] | 95.6 | [{"value": 95.0, "product": "OC1=C(N=C2C(OCCN2C1=O)C)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.6, "product": "OC1=C(N=C2C(OCCN2C1=O)C)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Hydrogenolysis of intermediate 14, ethyl 3-benzyloxy-9-methyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylate, (0.610 g, 1.77 mmol) in a mixture of ethyl acetate (75 ml) and ethanol (75 ml) at 25° C. over 10% palladium on activated carbon (0.20 g) under 1 atm of hydrogen for 2 h gave 0.430 g (95% yiel... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1cnc2n(c1)CCO[CH]2 | Other | [Pd].C(C)(=O)OCC.C(C)O | null | null | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2C>[Pd].C(C)(=O)OCC.C(C)O>CCOC(=O)c1nc2n(c(=O)c1O)CCOC2C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-110553af96dd488c97415d9811a0c00b | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2C>>CC1OCCn2c1nc(C(=O)O)c(OCc1ccccc1)c2=O | C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)C)C(=O)OCC>>C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)C)C(=O)O | CC[O:12][C:10]([c:9]1[n:8][c:7]2[n:6]([c:22](=[O:23])[c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[CH2:5][CH2:4][O:3][CH:2]2[CH3:1])=[O:11]>>[CH3:1][CH:2]1[O:3][CH2:4][CH2:5][n:6]2[c:7]1[n:8][c:9]([C:10](=[O:11])[OH:12])[c:13]([O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]2=[O:23] | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2C | CC1OCCn2c1nc(C(=O)O)c(OCc1ccccc1)c2=O | null | null | C(C)(=O)OCC.CCCCCC | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1c(OCc2ccccc2)cnc2n1CCOC2 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 96 | [{"value": 96.0, "product": "C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Saponification of intermediate 14, ethyl 3-benzyloxy-9-methyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylate, (0.225 g, 0.65 mmol) as described in the preparation of intermediate 7 gave 0.198 g (96% yield) of the title acid as white crystals; mp 167-168° C. (ethyl acetate-hexane). 1HNMR 400 MHz (CDCl... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cnc2n(c1)CCO[CH]2.c1ccccc1 | Other | C(C)(=O)OCC.CCCCCC | null | null | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2C>C(C)(=O)OCC.CCCCCC>CC1OCCn2c1nc(C(=O)O)c(OCc1ccccc1)c2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a6cfdad163f4f679e5626af00745182 | CSCCC=O.OCCO>>CSCCC1OCCO1 | CSCCC=O.C(CO)O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>CSCCC1OCCO1 | [CH3:1][S:2][CH2:3][CH2:4][CH:5]=[O:6].O[CH2:7][CH2:8][OH:9]>>[CH3:1][S:2][CH2:3][CH2:4][CH:5]1[O:6][CH2:7][CH2:8][O:9]1 | CSCCC=O.OCCO | CSCCC1OCCO1 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | fe0fbb45a87f24c1e456c6b4e41101562cd8f0af3ec376bb6115e7c1555d997b | 7ac65b5a5f576337ce8e86e0130eb9b4757ca21b2419a0e82bbdfd5def30ee73 | C1COCO1 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[C:4]-[C:5]-[CH;D2;+0:6]=[O;H0;D1;+0:7]>>[C:4]-[C:5]-[CH;D3;+0:6]1-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1 | null | [] | null | null | null | null | A solution of 3-(methylthio)propanal (5.2 g, 0.05 mol) and ethyleneglycol (3.4g. 0.055 mol) in 100 mL of benzene was treated with 300 mg p-toluenesulfonic acid and heated at reflux for 4 hrs. The solution was cooled and decanted. Concentration and drying in vacuo provided the title compound as a light yellow oil. 1H NM... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCO1 | C1COCO1 | HO- | C1=CC=CC=C1 | null | null | CSCCC=O.OCCO>C1=CC=CC=C1>CSCCC1OCCO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1dd8fca67b874a688e2ad49b85dbc1d1 | CSCCC(C#N)OCCO[Si](C)(C)C.N>>CSCCC(OCCO[Si](C)(C)C)C(=N)N | CSCCC(C#N)OCCO[Si](C)(C)C.N>>CSCCC(C(=N)N)OCCO[Si](C)(C)C | [CH3:1][S:2][CH2:3][CH2:4][CH:5]([O:6][CH2:7][CH2:8][O:9][Si:10]([CH3:11])([CH3:12])[CH3:13])[C:14]#[N:15].[NH3:16]>>[CH3:1][S:2][CH2:3][CH2:4][CH:5]([O:6][CH2:7][CH2:8][O:9][Si:10]([CH3:11])([CH3:12])[CH3:13])[C:14](=[NH:15])[NH2:16] | CSCCC(C#N)OCCO[Si](C)(C)C.N | CSCCC(OCCO[Si](C)(C)C)C(=N)N | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 080bc392517146a8e4e2652444810e882b6d922fa0c927a2aa6ffbd2ba45a361 | 807c02e8854fa1d85bad1ac2ebd73d5cdddf0728c08cb10c1d1278b952c720d7 | null | [#8:1]-[C:2](-[C:3])-[C;H0;D2;+0:4]#[N;H0;D1;+0:5].[NH3;D0;+0:6]>>[#8:1]-[C:2](-[C:3])-[C;H0;D3;+0:4](-[NH2;D1;+0:6])=[NH;D1;+0:5] | null | [] | 85 | CELSIUS | null | null | A solution of intermediate 18, 4-(methylthio)-2-(2-(trimethylsilyloxy)ethoxy)butanenitrile, (4.9 g, 0.02 mol) in 30 mL of methanol was saturated with ammonia. The flask was then sealed and heated in an oil bath at 80-90° C. for 16 hrs. After cooling, the flask was opened and the mixture concentrated in vacuo to give th... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | null | null | CO | 85 | null | CSCCC(C#N)OCCO[Si](C)(C)C.N>CO>CSCCC(OCCO[Si](C)(C)C)C(=N)N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0056a5d036354ceb9d834db32c6ae8e5 | CCOC(=O)c1nc(C(CCSC)OCCO)[nH]c(=O)c1OCc1ccccc1>>CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2CCSC | CSOC(=O)I.C(C1=CC=CC=C1)OC1=C(N=C(NC1=O)C(CCSC)OCCO)C(=O)OCC.CCN(CC)CC>>C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)CCSC)C(=O)OCC | O[CH2:21][CH2:22][O:23][CH:24]([c:8]1[n:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:12]([O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:10](=[O:11])[nH:9]1)[CH2:25][CH2:26][S:27][CH3:28]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]2[n:9]([c:10](=[O:11])[c:12]1[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18]... | CCOC(=O)c1nc(C(CCSC)OCCO)[nH]c(=O)c1OCc1ccccc1 | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2CCSC | null | null | CCOCC.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 3d4dd7481546b89bdfc13d988499cecab9925696be00935421ee0a9674a0a7e2 | 2ab4024aa17b6e89368e6fe8ee731d32c7611cb9b23de403e301e8362fea90b1 | O=c1c(OCc2ccccc2)cnc2n1CCOC2 | O-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[c:5]1:[#7;a:6]:[c:7](-[C:8](-[#8:9])=[O;D1;H0:10]):[c:11]:[c:12](=[O;D1;H0:13]):[nH;D2;+0:14]:1>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#7;a:6]:[c:5]2:[n;H0;D3;+0:14](:[c:12](=[O;D1;H0:13]):[c:11]:1)-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-2 | 52.4 | [{"value": 52.0, "product": "C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)CCSC)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.4, "product": "C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)CCSC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | To a solution of intermediate 20, ethyl 5-(benzyloxy)-2-(1-(2-hydroxyethoxy)-3-(methylthio)propyl)-6-oxo-1,6-dihydropyrimidine-4-carboxylate, (527 mg, 1.25 mmol) and Et3N (505 mg, 5 mmol) dissolved in 10 mL of CH2Cl2 was added a solution of CH3SO2CI (288 mg, 2.5 mmol) dissolved in 2 mL of CH2Cl2. This was stirred for 2... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | c1cncnc1 | c1cnc2n(c1)CCO[CH]2 | c1ccccc1.c1cnc2n(c1)CCO[CH]2 | HO- | CCOCC.C(Cl)Cl | null | 20 | CCOC(=O)c1nc(C(CCSC)OCCO)[nH]c(=O)c1OCc1ccccc1>CCOCC.C(Cl)Cl>CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2CCSC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5291017c03be47b0ae782e7a8b38a8ce | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2CCSC>>CSCCC1OCCn2c1nc(C(=O)O)c(OCc1ccccc1)c2=O | Cl.C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)CCSC)C(=O)OCC.[OH-].[Li+]>>C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)CCSC)C(=O)O | CC[O:15][C:13]([c:12]1[n:11][c:10]2[n:9]([c:25](=[O:26])[c:16]1[O:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[CH2:8][CH2:7][O:6][CH:5]2[CH2:4][CH2:3][S:2][CH3:1])=[O:14]>>[CH3:1][S:2][CH2:3][CH2:4][CH:5]1[O:6][CH2:7][CH2:8][n:9]2[c:10]1[n:11][c:12]([C:13](=[O:14])[OH:15])[c:16]([O:17][CH2:18][c:19]1[cH:20][... | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2CCSC | CSCCC1OCCn2c1nc(C(=O)O)c(OCc1ccccc1)c2=O | null | null | O1CCCC1.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1c(OCc2ccccc2)cnc2n1CCOC2 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 108.9 | [{"value": 88.0, "product": "C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)CCSC)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 108.9, "product": "C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)CCSC)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of intermediate 21, ethyl 3-(benzyloxy)-9-(2-(methylthio)ethyl)-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylate (97 mg, 0.2mmol) in 3 mL tetrahydrofuran was added lithium hydroxide (1 5 mg, 0.6 mmol) in 3 mL water. After 20 min the reaction mixture was acidified with 1N HCl and e... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cnc2n(c1)CCO[CH]2.c1ccccc1 | Other | O1CCCC1.O | null | null | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2CCSC>O1CCCC1.O>CSCCC1OCCn2c1nc(C(=O)O)c(OCc1ccccc1)c2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-124c1e87c7ed41acb94650cfba9e2194 | CC(C)(O)C#N.OCCCl>>CC(C)(C#N)OCCCl | CC(C#N)(O)C.ClCCO>>ClCCOC(C#N)(C)C | O[C:2]([CH3:1])([CH3:3])[C:4]#[N:5].[OH:6][CH2:7][CH2:8][Cl:9]>>[CH3:1][C:2]([CH3:3])([C:4]#[N:5])[O:6][CH2:7][CH2:8][Cl:9] | CC(C)(O)C#N.OCCCl | CC(C)(C#N)OCCCl | null | [Cl-].[Cl-].[Zn+2] | O | Heteroatom Alkylation and Arylation | Alcohol to ether | 684823df159a4c07d0a2a3c5a4e8843a8449fd560dd00a2ccbb32e95f87ee6bc | 71d6b370ca48f1d75269bb2a372b1608a88e28617e379e11884cc0e510f32096 | null | O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4]#[N;D1;H0:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4]#[N;D1;H0:5] | 63.8 | [{"value": 63.8, "product": "ClCCOC(C#N)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.8, "product": "ClCCOC(C#N)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 19 | HOUR | (Navalokina, R. Et al J. Org. Chem. USSR (Engl. Trans.), 1980, 16, 1382-1386. 2) Ramalingam, K. U.S. Pat. No. 4,864,051, 1989.). A 250 mL round bottom flask was charged with ZnCl2 (68.14 g, 0.5 mole) which was then fused by heating under vacuum. After returning to room temperature the material was placed under an atmos... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary alcohol | Ether | null | null | null | HO- | [Cl-].[Cl-].[Zn+2].O | 60 | 19 | CC(C)(O)C#N.OCCCl>[Cl-].[Cl-].[Zn+2].O>CC(C)(C#N)OCCCl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4f89fd02f88441029ad2c55e62c0b6f5 | CC(C)(C#N)OCCCl.CCOC(=O)C#CC(=O)OCC.NO>>CCOC(=O)CC1(C(=O)OCC)N=C2N(CCOC2(C)C)O1 | ClCCOC(C#N)(C)C.[Na+].[I-].NO.C(#CC(=O)OCC)C(=O)OCC>>C(C)OC(CC1(N=C2C(OCCN2O1)(C)C)C(=O)OCC)=O | Cl[CH2:16][CH2:17][O:18][C:19]([C:14]#[N:13])([CH3:20])[CH3:21].[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]#[C:7][C:8](=[O:9])[O:10][CH2:11][CH3:12].[NH2:15][OH:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7]1([C:8](=[O:9])[O:10][CH2:11][CH3:12])[N:13]=[C:14]2[N:15]([CH2:16][CH2:17][O:18][C:19]2([CH3:20])[CH3:21])[O:22]1 | CC(C)(C#N)OCCCl.CCOC(=O)C#CC(=O)OCC.NO | CCOC(=O)CC1(C(=O)OCC)N=C2N(CCOC2(C)C)O1 | null | null | C(C)(=O)OCC.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | a5917d702028448357f7058ae5e40c87e2d8f4c235ca1dccfb49bd3cb6625926 | 69880389a496532f744726aac1f0914237c6d43769e736157ffa6a51cc5861a0 | C1CN2OCN=C2CO1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;H0;D2;+0:7]#[N;H0;D1;+0:8].[C:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[C;H0;D2;+0:13]#[C;H0;D2;+0:14]-[C:15](=[O;D1;H0:16])-[#8:17]-[C:18].[NH2;D1;+0:19]-[OH;D1;+0:20]>>[C:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[C;H0;D4;+0:13]1(-[CH2;D2;+0:14]-[C:15](=[O;D1;H0:16])-... | 48.6 | [{"value": 48.6, "product": "C(C)OC(CC1(N=C2C(OCCN2O1)(C)C)C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.6, "product": "C(C)OC(CC1(N=C2C(OCCN2O1)(C)C)C(=O)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 1 | HOUR | To a stirred solution of intermediate 23, 2-(2-chloroethoxy)-2-methylpropanenitrile (14.7 g, 0.10 mole) and NaI (1.5 g, 10 mmol) in ethanol (50 mL) was added an aqueous solution (50%) of hydroxylamine (18.4 g, 0.30 mole) resulting in an exothermic reaction. Following this the reaction mixture was heated at 80° C. for 2... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester.Nitrile.Primary amine | Ester.Ester.Tertiary amine | null | C1CN2OCN=C2CO1 | C1CN2OCN=C2CO1 | HCl | C(C)(=O)OCC.C(C)O | 80 | 1 | CC(C)(C#N)OCCCl.CCOC(=O)C#CC(=O)OCC.NO>C(C)(=O)OCC.C(C)O>CCOC(=O)CC1(C(=O)OCC)N=C2N(CCOC2(C)C)O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a1e0766d68d419a8ed9541ae0e65e6a | CCOC(=O)CC1(C(=O)OCC)N=C2N(CCOC2(C)C)O1>>CCOC(=O)c1nc2n(c(=O)c1O)CCOC2(C)C | C(C)OC(CC1(N=C2C(OCCN2O1)(C)C)C(=O)OCC)=O.C(C)(=O)OCC>>OC1=C(N=C2C(OCCN2C1=O)(C)C)C(=O)OCC | CCO[C:10](=[O:11])[CH2:12][C:6]1([C:4]([O:3][CH2:2][CH3:1])=[O:5])[N:7]=[C:8]2[N:9]([O:13]1)[CH2:14][CH2:15][O:16][C:17]2([CH3:18])[CH3:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]2[n:9]([c:10](=[O:11])[c:12]1[OH:13])[CH2:14][CH2:15][O:16][C:17]2([CH3:18])[CH3:19] | CCOC(=O)CC1(C(=O)OCC)N=C2N(CCOC2(C)C)O1 | CCOC(=O)c1nc2n(c(=O)c1O)CCOC2(C)C | null | null | CC1=C(C=C(C=C1)C)C.CCOCC | Aromatic Heterocycle Formation | OtherReaction | a03f9eaa5e7eb0271a37ed1901b591f530bbce8c6ece25823a3d06c99dead24a | fa33563db5d782f36d1ac7f6cdbda7c5595318d1e5a1cdb5a6a9b112b123a622 | O=c1ccnc2n1CCOC2 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[C;H0;D4;+0:4]1(-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8])-[N;H0;D2;+0:9]=[C;H0;D3;+0:10]2-[N;H0;D3;+0:11](-[C:12]-[C:13]-[#8:14]-[C:15]-2(-[C;D1;H3:16])-[C;D1;H3:17])-[O;H0;D2;+0:18]-1>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:4]1:[n;H0;D2;+0:9]:[c;H0;D3;+0:10]2:[n;H0;D3;+0... | 18 | [{"value": 18.0, "product": "OC1=C(N=C2C(OCCN2C1=O)(C)C)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of intermediate 24, ethyl 2-(2-ethoxy-2-oxoethyl)-8,8-dimethyl-2,5,6,8-tetrahydro-[1,2,4]oxadiazolo[3,2-c][1,4]oxazine-2-carboxylate (31.16 g) in 1,2,4-trimethylbenzene (200 mL) was heated at 180° C. for 5 h. The resulting dark reaction solution was cooled then concentrated to give a dark brown paste which w... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Tertiary amine | Ester.Aromatic alcohol | C1CN2OCN=C2CO1 | C1OCCn2cccnc21 | C1OCCn2cccnc21 | HO- | CC1=C(C=C(C=C1)C)C.CCOCC | null | null | CCOC(=O)CC1(C(=O)OCC)N=C2N(CCOC2(C)C)O1>CC1=C(C=C(C=C1)C)C.CCOCC>CCOC(=O)c1nc2n(c(=O)c1O)CCOC2(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-46e52e1d4b404d63aee04a451e7bd9d5 | BrCc1ccccc1.CCOC(=O)c1nc2n(c(=O)c1O)CCOC2(C)C>>CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2(C)C | OC1=C(N=C2C(OCCN2C1=O)(C)C)C(=O)OCC.C(C1=CC=CC=C1)Br.C(=O)([O-])[O-].[K+].[K+]>>C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)(C)C)C(=O)OCC | Br[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]2[n:9]([c:10](=[O:11])[c:12]1[OH:13])[CH2:21][CH2:22][O:23][C:24]2([CH3:25])[CH3:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]2[n:9]([c:10](=[O:11])[c:12]1[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20... | BrCc1ccccc1.CCOC(=O)c1nc2n(c(=O)c1O)CCOC2(C)C | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2(C)C | null | null | CCOCC.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=c1c(OCc2ccccc2)cnc2n1CCOC2 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11](:[c:12](=[O;D1;H0:13]):[c:14]:1-[OH;D1;+0:15])-[C:16]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[#7;a:9]:[c:10]:[#7;a:11](:[c:12](=[O;D1;H0:13]):[c:14]:1-[O;H0;D2;+0:15]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:16] | 78 | [{"value": 78.0, "product": "C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)(C)C)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)(C)C)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | To a stirred solution of intermediate 25, ethyl 3-hydroxy-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4]oxazine-2-carboxylate, (2.68 g, 10 mmol) and benzyl bromide (1.43 mL, 12 mmol) in DMF (40 mL) was added K2CO3 (2.07 g, 20 mmol). After stirring 48 h at ambient temperature, the reaction mixture was diluted... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1OCCn2cccnc21 | HBr | CCOCC.CN(C)C=O | null | 48 | BrCc1ccccc1.CCOC(=O)c1nc2n(c(=O)c1O)CCOC2(C)C>CCOCC.CN(C)C=O>CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-063cc7d486744680af9ee528e8b6a26a | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2(C)C>>CC1(C)OCCn2c1nc(C(=O)O)c(OCc1ccccc1)c2=O | C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)(C)C)C(=O)OCC.O[Li].O>>C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)(C)C)C(=O)O | CC[O:13][C:11]([c:10]1[n:9][c:8]2[n:7]([c:23](=[O:24])[c:14]1[O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[CH2:6][CH2:5][O:4][C:2]2([CH3:1])[CH3:3])=[O:12]>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][CH2:6][n:7]2[c:8]1[n:9][c:10]([C:11](=[O:12])[OH:13])[c:14]([O:15][CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22... | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2(C)C | CC1(C)OCCn2c1nc(C(=O)O)c(OCc1ccccc1)c2=O | null | null | C(C)O.O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1c(OCc2ccccc2)cnc2n1CCOC2 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 99 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)(C)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.9, "product": "C(C1=CC=CC=C1)OC1=C(N=C2C(OCCN2C1=O)(C)C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of intermediate 26, ethyl 3-(benzyloxy)-9,9-dimethyl-4-oxo-4,6,7,9-tetrahydropyrimido[2,1-c][1,4] oxazine-2-carboxylate, (2.93 g, 8.2 mmol) and LiOH.H2O (0.84 g, 20 mmol) in 4:1 ethanol/tetrahydrofuran (50 mL) was stirred for 2 h at ambient temperature then concentrated under vacuum. The resulting yellow resi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1OCCn2cccnc21.c1ccccc1 | Other | C(C)O.O1CCCC1 | null | 2 | CCOC(=O)c1nc2n(c(=O)c1OCc1ccccc1)CCOC2(C)C>C(C)O.O1CCCC1>CC1(C)OCCn2c1nc(C(=O)O)c(OCc1ccccc1)c2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7e02cac3d14d472a81bae5ec19de709e | CCC(O)(C#N)CC.OCCCl>>CCC(C#N)(CC)OCCCl | C(C)C(C#N)(CC)O.ClCCO>>ClCCOC(C#N)(CC)CC | [CH3:1][CH2:2][C:3]([C:4]#[N:5])([CH2:6][CH3:7])[OH:8].O[CH2:9][CH2:10][Cl:11]>>[CH3:1][CH2:2][C:3]([C:4]#[N:5])([CH2:6][CH3:7])[O:8][CH2:9][CH2:10][Cl:11] | CCC(O)(C#N)CC.OCCCl | CCC(C#N)(CC)OCCCl | null | [Cl-].[Zn+2].[Cl-].[Zn] | O | Heteroatom Alkylation and Arylation | Alcohol to ether | 684823df159a4c07d0a2a3c5a4e8843a8449fd560dd00a2ccbb32e95f87ee6bc | 71d6b370ca48f1d75269bb2a372b1608a88e28617e379e11884cc0e510f32096 | null | O-[CH2;D2;+0:1]-[C:2]-[Cl;D1;H0:3].[C:4]-[C:5](-[C:6])(-[OH;D1;+0:7])-[C:8]#[N;D1;H0:9]>>[C:4]-[C:5](-[C:6])(-[C:8]#[N;D1;H0:9])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[Cl;D1;H0:3] | 39,471.1 | [{"value": 39471.1, "product": "ClCCOC(C#N)(CC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 20 | HOUR | Zinc chloride (68.1 g, 0.5 mol) was fused under vacuum as described in the procedure for the synthesis of intermediate 23. The molten zinc was cooled and the evacuated flask was flushed with nitrogen. The flask was loaded with intermediate 28, 2-ethyl-2-hydroxybutanenitrile, (40.3 g, 0.5 mol) and 2-chloroethanol (50.5 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary alcohol | Ether | null | null | null | HO- | [Cl-].[Zn+2].[Cl-].[Zn].O | 60 | 20 | CCC(O)(C#N)CC.OCCCl>[Cl-].[Zn+2].[Cl-].[Zn].O>CCC(C#N)(CC)OCCCl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ab0304298cbf48caa8874bbebe443ba8 | BrCc1ccccc1.CCOC(=O)c1nc(C(C)(C)OCCCCl)[nH]c(=O)c1O>>CC1(C)OCCCn2c1nc(C(=O)O)c(OCc1ccccc1)c2=O | C(C1=CC=CC=C1)Br.ClCCCOC(C)(C)C=1NC(C(=C(N1)C(=O)OCC)O)=O.C([O-])([O-])=O.[K+].[K+].O>>C(C1=CC=CC=C1)OC1=C(N=C2C(OCCCN2C1=O)(C)C)C(=O)O | Br[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1.CC[O:14][C:12]([c:11]1[n:10][c:9]([C:2]([CH3:1])([CH3:3])[O:4][CH2:5][CH2:6][CH2:7]Cl)[nH:8][c:24](=[O:25])[c:15]1[OH:16])=[O:13]>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][CH2:6][CH2:7][n:8]2[c:9]1[n:10][c:11]([C:12](=[O:13])[OH:14])[c:15]([O:16][CH2:17][c:18]1[cH:19][cH:... | BrCc1ccccc1.CCOC(=O)c1nc(C(C)(C)OCCCCl)[nH]c(=O)c1O | CC1(C)OCCCn2c1nc(C(=O)O)c(OCc1ccccc1)c2=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | de0a20280e677f94ca9d770b04253e74f22df4e7b24d912058580f57db6b1057 | 623e79ee6d04301e24a593b393382fd53fb40863aab75093f67aae06cd334cb4 | O=c1c(OCc2ccccc2)cnc2n1CCCOC2 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].C-C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[#7;a:9]:[c:10](-[C:11]):[nH;D2;+0:12]:[c:13](=[O;D1;H0:14]):[c:15]:1-[OH;D1;+0:16].Cl-[CH2;D2;+0:17]-[C:18]-[C:19]>>[C:11]-[c:10]1:[#7;a:9]:[c:8](-[C:6](=[O;D1;H0:7])-[OH;D1;+0:5]):[c:15](-[O;H0;D2;+0:16]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:... | 135.7 | [{"value": 100.0, "product": "C(C1=CC=CC=C1)OC1=C(N=C2C(OCCCN2C1=O)(C)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 135.7, "product": "C(C1=CC=CC=C1)OC1=C(N=C2C(OCCCN2C1=O)(C)C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 5 | HOUR | A suspension of intermediate 33, ethyl 2-(2-(3-chloropropoxy)propan-2-yl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate, (0.205 g, 0.64 mmol) and anhydrous potassium carbonate (0.361 g, 2.6 mmol) in anhydrous dimethylformamide (4 mL) was stirred at 60° C. for 5 hours. The reaction mixture was treated with benzyl ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Ester.Aromatic alcohol | Carboxylic acid.Ether | c1cncnc1 | C1OCCCn2cccnc21 | C1OCCCn2cccnc21.c1ccccc1 | HCl.Br- | CN(C=O)C | 60 | 5 | BrCc1ccccc1.CCOC(=O)c1nc(C(C)(C)OCCCCl)[nH]c(=O)c1O>CN(C=O)C>CC1(C)OCCCn2c1nc(C(=O)O)c(OCc1ccccc1)c2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-68aee97f0d9f4ec9b2a3d3c7715b29a2 | N#Cc1ccc(F)c2ccccc12>>NCc1ccc(F)c2ccccc12 | C(#N)C1=CC=C(C2=CC=CC=C12)F.Cl>>Cl.FC1=CC=C(C2=CC=CC=C12)CN | [N:2]#[C:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12>>[NH2:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12 | N#Cc1ccc(F)c2ccccc12 | NCc1ccc(F)c2ccccc12 | null | [Pd] | C(C)O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc2ccccc2c1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 44 | [{"value": 44.0, "product": "Cl.FC1=CC=C(C2=CC=CC=C12)CN", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-cyano-4-fluoronapthalene (1.05 g, 6.12 mmol) and 1.5 mL of HCl (aq.) in absolute ethanol (50 mL) was stirred under a hydrogen atmosphere (balloon) with 10% palladium on carbon (0.20 g) for 16 hours. The catalyst was removed by filtration through Celite, and the filtrate concentrated under vacuum. The re... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccc2ccccc2c1 | null | [Pd].C(C)O | null | null | N#Cc1ccc(F)c2ccccc12>[Pd].C(C)O>NCc1ccc(F)c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2fb731be3faf44ceab7ee9f2b74b19ef | CNC(=O)c1cc(F)ccc1CNC(=O)OC(C)(C)C>>CNC(=O)c1cc(F)ccc1CN | FC1=CC(=C(CNC(OC(C)(C)C)=O)C=C1)C(NC)=O.C(F)(F)(F)C(=O)O>>FC(C(=O)O)(F)F.NCC1=C(C(=O)NC)C=C(C=C1)F | CC(C)(C)OC(=O)[NH:13][CH2:12][c:11]1[c:5]([C:3]([NH:2][CH3:1])=[O:4])[cH:6][c:7]([F:8])[cH:9][cH:10]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]1[CH2:12][NH2:13] | CNC(=O)c1cc(F)ccc1CNC(=O)OC(C)(C)C | CNC(=O)c1cc(F)ccc1CN | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[c:3]>>[NH2;D1;+0:1]-[C:2]-[c:3] | 99 | [{"value": 99.0, "product": "FC(C(=O)O)(F)F.NCC1=C(C(=O)NC)C=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of tert-butyl 4-fluoro-2-(methylcarbamoyl)benzylcarbamate (7.70 g, 27.3 mmol; prepared from 2-bromo-5-fluorobenzoic acid using literature methods) in CH2Cl2 (100 mL) was added CF3CO2H (25 mL) and the mixture stirred at room temperature for 15 min. This was concentrated in vacuo and the residue triturated ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | C(Cl)Cl | null | 0.25 | CNC(=O)c1cc(F)ccc1CNC(=O)OC(C)(C)C>C(Cl)Cl>CNC(=O)c1cc(F)ccc1CN |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c45a397e4adf4ad7891030fc2fdac556 | CC(C)(C)OC(=O)NCc1ccc(F)cc1C(=O)NC1CC1>>NCc1ccc(F)cc1C(=O)NC1CC1 | C1(CC1)NC(=O)C1=C(CNC(OC(C)(C)C)=O)C=CC(=C1)F.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.NCC1=C(C(=O)NC2CC2)C=C(C=C1)F | CC(C)(C)OC(=O)[NH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]1[C:10](=[O:11])[NH:12][CH:13]1[CH2:14][CH2:15]1>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]1[C:10](=[O:11])[NH:12][CH:13]1[CH2:14][CH2:15]1 | CC(C)(C)OC(=O)NCc1ccc(F)cc1C(=O)NC1CC1 | NCc1ccc(F)cc1C(=O)NC1CC1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(NC1CC1)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[c:3]>>[NH2;D1;+0:1]-[C:2]-[c:3] | 100 | [{"value": 100.0, "product": "FC(C(=O)O)(F)F.NCC1=C(C(=O)NC2CC2)C=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of tert-butyl 2-(cyclopropylcarbamoyl)-4-fluorobenzylcarbamate (130 mg, 0.42 mmol) prepared according to literature methods, in CH2Cl2 (5 mL) was stirred with trifluoroacetic acid (3 mL) at room temperature for 10 min, then concentrated in vacuo to give 140 mg (Yield 100%) of the title compound as a foam: 1H... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.C1CC1 | HO- | C(Cl)Cl | null | null | CC(C)(C)OC(=O)NCc1ccc(F)cc1C(=O)NC1CC1>C(Cl)Cl>NCc1ccc(F)cc1C(=O)NC1CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6d16ec3a7661481db1600a6c44137855 | C1COCCN1.Cc1ccc(F)cc1C(=O)Cl>>Cc1ccc(F)cc1C(=O)N1CCOCC1 | N1CCOCC1.C(C)N(CC)CC.FC=1C=CC(=C(C(=O)Cl)C1)C>>FC=1C=CC(=C(C1)C(=O)N1CCOCC1)C | [NH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1.Cl[C:9]([c:8]1[c:2]([CH3:1])[cH:3][cH:4][c:5]([F:6])[cH:7]1)=[O:10]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([F:6])[cH:7][c:8]1[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1 | C1COCCN1.Cc1ccc(F)cc1C(=O)Cl | Cc1ccc(F)cc1C(=O)N1CCOCC1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b2821ffedb27fdb32ee8909e6c37f5667f3a9287b29ba6c49c7967ceba44bfc3 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCOCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1)-[c:3](:[c:4]):[c:5] | 98.1 | [{"value": 98.0, "product": "FC=1C=CC(=C(C1)C(=O)N1CCOCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.1, "product": "FC=1C=CC(=C(C1)C(=O)N1CCOCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of morpholine (870 mg, 10 mmol) and triethylamine (1.1 g, 10.8 mmol) in CH2Cl2 (15 mL) was added a solution of 5-fluoro-2-methylbenzoyl chloride (1.72 g, 10 mmol) in CH2Cl2 (5 mL), dropwise, and the mixture stirred for 15 min. The mixture was then washed with water, and the organic phase dried (MgSO4), fi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HCl | C(Cl)Cl | null | 0.25 | C1COCCN1.Cc1ccc(F)cc1C(=O)Cl>C(Cl)Cl>Cc1ccc(F)cc1C(=O)N1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f400d2481d4e4586a73dfda45b1fec36 | Cc1ccc(F)cc1C(=O)N1CCOCC1.O=C1CCC(=O)N1Br>>O=C(c1cc(F)ccc1CBr)N1CCOCC1 | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.FC=1C=CC(=C(C1)C(=O)N1CCOCC1)C.BrN1C(CCC1=O)=O>>BrCC1=C(C=C(C=C1)F)C(=O)N1CCOCC1 | [O:1]=[C:2]([c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[CH3:10])[N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1.O=C1CCC(=O)N1[Br:11]>>[O:1]=[C:2]([c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[CH2:10][Br:11])[N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1 | Cc1ccc(F)cc1C(=O)N1CCOCC1.O=C1CCC(=O)N1Br | O=C(c1cc(F)ccc1CBr)N1CCOCC1 | null | null | null | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | O=C(c1ccccc1)N1CCOCC1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[CH3;D1;+0:7]):[c:8]>>[#7:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[CH2;D2;+0:7]-[Br;H0;D1;+0:1]):[c:8] | 38.3 | [{"value": 38.0, "product": "BrCC1=C(C=C(C=C1)F)C(=O)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.3, "product": "BrCC1=C(C=C(C=C1)F)C(=O)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of intermediate 41, (5-fluoro-2-methylphenyl)(morpholino)methanone, (2.1 g, 9.5 mmol) and N-bromosuccinimide (2.0 g, 11 mmol) in CCl14 (30 mL) was heated at reflux. To this mixture was added benzoylperoxide (242 mg, 1 mmol) and the mixture heated at reflux for 2 hrs. After cooling, the insoluble materials wer... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1.C1COCC[NH]1 | HO- | null | null | null | Cc1ccc(F)cc1C(=O)N1CCOCC1.O=C1CCC(=O)N1Br>>O=C(c1cc(F)ccc1CBr)N1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f9c750b9df7c47f889d1206627e75429 | O=C(c1cc(F)ccc1CBr)N1CCOCC1.[N-]=[N+]=[N-]>>[N-]=[N+]=NCc1ccc(F)cc1C(=O)N1CCOCC1 | BrCC1=C(C=C(C=C1)F)C(=O)N1CCOCC1.[N-]=[N+]=[N-].[Na+]>>N(=[N+]=[N-])CC1=C(C=C(C=C1)F)C(=O)N1CCOCC1 | Br[CH2:4][c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[C:12](=[O:13])[N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1.[N-:1]=[N+:2]=[N-:3]>>[N-:1]=[N+:2]=[N:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[C:12](=[O:13])[N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1 | O=C(c1cc(F)ccc1CBr)N1CCOCC1.[N-]=[N+]=[N-] | [N-]=[N+]=NCc1ccc(F)cc1C(=O)N1CCOCC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 4b07a4c2a14d792a37e78a751619e60b15c60cbff0bebae1109754fb52d84cbb | 2d41632f7225d65cdc2ad8562dfb28f3f5a017f92040ed4ccafbb8154954c8fe | O=C(c1ccccc1)N1CCOCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#7:6])=[O;D1;H0:7].[N-;H0;D1:8]=[#7;+:9]=[N;-;D1;H0:10]>>[#7:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[CH2;D2;+0:1]-[N;H0;D2;+0:8]=[#7;+:9]=[N;-;D1;H0:10]):[c:3] | 88 | [{"value": 88.0, "product": "N(=[N+]=[N-])CC1=C(C=C(C=C1)F)C(=O)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.8, "product": "N(=[N+]=[N-])CC1=C(C=C(C=C1)F)C(=O)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of intermediate 42, (2-(bromomethyl)-5-fluorophenyl)(morpholino)methanone, (1.0 g, 3.32 mmol) in dimethylformamide (10 mL) was added sodium azide (230 mg, 3.5 mmol) and the mixture stirred under a nitrogen atmosphere for 1 h. The solvent was evaporated in vacuo, and the residue dissolved in CH2Cl2, then w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Azide | null | null | c1ccccc1.C1COCC[NH]1 | Br- | CN(C=O)C | null | 1 | O=C(c1cc(F)ccc1CBr)N1CCOCC1.[N-]=[N+]=[N-]>CN(C=O)C>[N-]=[N+]=NCc1ccc(F)cc1C(=O)N1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac032dcc7126421b87dbb8808b81f018 | CNC.Cc1ccc(F)cc1S(=O)(=O)Cl>>Cc1ccc(F)cc1S(=O)(=O)N(C)C | FC=1C=CC(=C(C1)S(=O)(=O)Cl)C.CNC>>FC=1C=CC(=C(C1)S(=O)(=O)N(C)C)C | [NH:12]([CH3:13])[CH3:14].Cl[S:9]([c:8]1[c:2]([CH3:1])[cH:3][cH:4][c:5]([F:6])[cH:7]1)(=[O:10])=[O:11]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([F:6])[cH:7][c:8]1[S:9](=[O:10])(=[O:11])[N:12]([CH3:13])[CH3:14] | CNC.Cc1ccc(F)cc1S(=O)(=O)Cl | Cc1ccc(F)cc1S(=O)(=O)N(C)C | null | null | O1CCCC1 | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) secondary amine | f885e88ea942f3030166da4c7f20dfb8bf6f1e152c7507d56458611df7dc3120 | 971e620478d668662a3bf915b510f5704d42a595d6ca9c67de007bd5d7063a75 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C;D1;H3:7]-[N;H0;D3;+0:8](-[C;D1;H3:9])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 90 | [{"value": 90.0, "product": "FC=1C=CC(=C(C1)S(=O)(=O)N(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 5-fluoro-2-methyl-benzenesulfonyl chloride (4.18 g, 20 mmol) in tetrahydrofuran (25 mL) was added, dropwise, a solution of dimethylamine in tetrahydrofuran (2M, 25 mL, 50 mmol) over 15 min. and the mixture stirred for 5 min. The insoluble materials were filtered and the filtrate concentrated. The resid... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | null | null | c1ccccc1 | HCl | O1CCCC1 | null | 0.083333 | CNC.Cc1ccc(F)cc1S(=O)(=O)Cl>O1CCCC1>Cc1ccc(F)cc1S(=O)(=O)N(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-43c328c276064e269b000c1cd2ba1bc1 | Cc1ccc(F)cc1S(=O)(=O)N(C)C.O=C1CCC(=O)N1Br>>CN(C)S(=O)(=O)c1cc(F)ccc1CBr | N(=NC(C#N)(C)C)C(C#N)(C)C.FC=1C=CC(=C(C1)S(=O)(=O)N(C)C)C.BrN1C(CCC1=O)=O>>BrCC1=C(C=C(C=C1)F)S(=O)(=O)N(C)C | [CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]1[CH3:14].O=C1CCC(=O)N1[Br:15]>>[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]1[CH2:14][Br:15] | Cc1ccc(F)cc1S(=O)(=O)N(C)C.O=C1CCC(=O)N1Br | CN(C)S(=O)(=O)c1cc(F)ccc1CBr | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 74.3 | [{"value": 74.0, "product": "BrCC1=C(C=C(C=C1)F)S(=O)(=O)N(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.3, "product": "BrCC1=C(C=C(C=C1)F)S(=O)(=O)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 5 | MINUTE | Under nitrogen, a mixture of intermediate 45, 5-fluoro-2,N,N-trimethyl-benzenesulfonamide, (435 mg, 2.0 mmol) and N-bromosuccinimide (391 mg, 2.2 mmol) in CCl4 (20 mL) was stirred at 80-90° C. for 5 min. To this mixture was added 2,2′-azobisisobutyronitrile (AIBN, 100 mg) and stirring continued at 80-90° C. for 30 min.... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(Cl)(Cl)(Cl)Cl | 85 | 0.083333 | Cc1ccc(F)cc1S(=O)(=O)N(C)C.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>CN(C)S(=O)(=O)c1cc(F)ccc1CBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae3c707c043f43aca3cf92f8e07f925a | CN(C)S(=O)(=O)c1cc(F)ccc1CBr.[N-]=[N+]=[N-]>>CN(C)S(=O)(=O)c1cc(F)ccc1CN=[N+]=[N-] | BrCC1=C(C=C(C=C1)F)S(=O)(=O)N(C)C.[N-]=[N+]=[N-].[Na+]>>N(=[N+]=[N-])CC1=C(C=C(C=C1)F)S(=O)(=O)N(C)C | Br[CH2:14][c:13]1[c:7]([S:4]([N:2]([CH3:1])[CH3:3])(=[O:5])=[O:6])[cH:8][c:9]([F:10])[cH:11][cH:12]1.[N-:15]=[N+:16]=[N-:17]>>[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]1[CH2:14][N:15]=[N+:16]=[N-:17] | CN(C)S(=O)(=O)c1cc(F)ccc1CBr.[N-]=[N+]=[N-] | CN(C)S(=O)(=O)c1cc(F)ccc1CN=[N+]=[N-] | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 4b07a4c2a14d792a37e78a751619e60b15c60cbff0bebae1109754fb52d84cbb | 2d41632f7225d65cdc2ad8562dfb28f3f5a017f92040ed4ccafbb8154954c8fe | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[N-;H0;D1:5]=[#7;+:6]=[N;-;D1;H0:7]>>[N;-;D1;H0:7]=[#7;+:6]=[N;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 87.3 | [{"value": 87.0, "product": "N(=[N+]=[N-])CC1=C(C=C(C=C1)F)S(=O)(=O)N(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.3, "product": "N(=[N+]=[N-])CC1=C(C=C(C=C1)F)S(=O)(=O)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 57.5 | CELSIUS | 30 | MINUTE | A mixture of intermediate 46, 2-bromomethyl-5-fluoro-N,N-dimethyl-benzenesulfonamide, (880 mg, 2.97 mmol) and sodium azide (200 mg, 3 mmol) in dimethylformamide (4 mL) was stirred at 55-60° C. for 30 min after which the solvent was removed in vacuo. The residue was partitioned between CH2Cl2 and water, and the organic ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Azide | null | null | c1ccccc1 | Br- | CN(C=O)C | 57.5 | 0.5 | CN(C)S(=O)(=O)c1cc(F)ccc1CBr.[N-]=[N+]=[N-]>CN(C=O)C>CN(C)S(=O)(=O)c1cc(F)ccc1CN=[N+]=[N-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-388c1aca927540cdb94fe526daca40c3 | CN(C)S(=O)(=O)c1cc(F)ccc1CN=[N+]=[N-]>>CN(C)S(=O)(=O)c1cc(F)ccc1CN | N(=[N+]=[N-])CC1=C(C=C(C=C1)F)S(=O)(=O)N(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>NCC1=C(C=C(C=C1)F)S(=O)(=O)N(C)C | [N-]=[N+]=[N:15][CH2:14][c:13]1[c:7]([S:4]([N:2]([CH3:1])[CH3:3])(=[O:5])=[O:6])[cH:8][c:9]([F:10])[cH:11][cH:12]1>>[CH3:1][N:2]([CH3:3])[S:4](=[O:5])(=[O:6])[c:7]1[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]1[CH2:14][NH2:15] | CN(C)S(=O)(=O)c1cc(F)ccc1CN=[N+]=[N-] | CN(C)S(=O)(=O)c1cc(F)ccc1CN | null | null | O1CCCC1.O | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | c1ccccc1 | [N-]=[N+]=[N;H0;D2;+0:1]-[C:2]-[c:3]>>[NH2;D1;+0:1]-[C:2]-[c:3] | 35 | [{"value": 35.0, "product": "NCC1=C(C=C(C=C1)F)S(=O)(=O)N(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.0, "product": "NCC1=C(C=C(C=C1)F)S(=O)(=O)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 1 | HOUR | To a solution of intermediate 47, 2-azidomethyl-5-fluoro-N,N-dimethyl-benzenesulfonamide, (660 mg, 2.6 mmol) in tetrahydrofuran (10 mL) and water (2 mL) was added triphenylphosphine (740 mg, 2.8 mmol), and the mixture stirred under nitrogen for 1 hr. The tetrahydrofuran was evaporated in vacuo and a mixture of the resi... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccccc1 | Other | O1CCCC1.O | 80 | 1 | CN(C)S(=O)(=O)c1cc(F)ccc1CN=[N+]=[N-]>O1CCCC1.O>CN(C)S(=O)(=O)c1cc(F)ccc1CN |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a9150065391045dd9e94b001e214dde4 | CN.Cc1ccc(F)cc1S(=O)(=O)Cl>>CNS(=O)(=O)c1cc(F)ccc1C | FC=1C=CC(=C(C1)S(=O)(=O)Cl)C.CN>>FC=1C=CC(=C(C1)S(=O)(=O)NC)C | [CH3:1][NH2:2].Cl[S:3](=[O:4])(=[O:5])[c:6]1[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]1[CH3:13]>>[CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]1[CH3:13] | CN.Cc1ccc(F)cc1S(=O)(=O)Cl | CNS(=O)(=O)c1cc(F)ccc1C | null | null | CC(=O)C | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 96 | [{"value": 96.0, "product": "FC=1C=CC(=C(C1)S(=O)(=O)NC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.0, "product": "FC=1C=CC(=C(C1)S(=O)(=O)NC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 5-fluoro-2-methyl-benzenesulfonyl chloride (4.18 g, 20 mmol) in acetone (20 mL) was added a 40% aqueous solution of methylamine (4.5 mL, 60 mmol) under nitrogen and the mixture stirred for 5 min. Acetone was removed in vacuo and the aqueous residue extracted with CH2Cl2. The CH2Cl2 extract was dried (N... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | CC(=O)C | null | 0.083333 | CN.Cc1ccc(F)cc1S(=O)(=O)Cl>CC(=O)C>CNS(=O)(=O)c1cc(F)ccc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2951742908a2472ab70fe369497278e0 | CNS(=O)(=O)c1cc(F)ccc1CN=[N+]=[N-]>>CNS(=O)(=O)c1cc(F)ccc1CN | N(=[N+]=[N-])CC1=C(C=C(C=C1)F)S(=O)(=O)NC.Cl>>Cl.NCC1=C(C=C(C=C1)F)S(=O)(=O)NC | [N-]=[N+]=[N:14][CH2:13][c:12]1[c:6]([S:3]([NH:2][CH3:1])(=[O:4])=[O:5])[cH:7][c:8]([F:9])[cH:10][cH:11]1>>[CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]1[CH2:13][NH2:14] | CNS(=O)(=O)c1cc(F)ccc1CN=[N+]=[N-] | CNS(=O)(=O)c1cc(F)ccc1CN | null | [Pd] | C(C)O | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | c1ccccc1 | [N-]=[N+]=[N;H0;D2;+0:1]-[C:2]-[c:3]>>[NH2;D1;+0:1]-[C:2]-[c:3] | 100 | [{"value": 100.0, "product": "Cl.NCC1=C(C=C(C=C1)F)S(=O)(=O)NC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of intermediate 51, 2-azidomethyl-5-fluoro-N-methyl-benzenesulfonamide, (560 mg, 2.3 mmol) in ethanol (10 mL) was added 6N HCl (1 mL) and 10% Pd—C (100 mg) and the mixture hydrogenated with 1 atm of H2 for 14 hrs. The catalyst was removed by filtration through Celite and the filtrate concentrated in vacuo... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)O | null | 14 | CNS(=O)(=O)c1cc(F)ccc1CN=[N+]=[N-]>[Pd].C(C)O>CNS(=O)(=O)c1cc(F)ccc1CN |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ddfe96bc6b2a4bb091b82ed029cae0e1 | Cc1ccc(F)cc1S(=O)(=O)Cl.[NH4+]>>Cc1ccc(F)cc1S(N)(=O)=O | FC=1C=CC(=C(C1)S(=O)(=O)Cl)C.[NH4+].[OH-]>>FC=1C=CC(=C(C1)S(=O)(=O)N)C | Cl[S:9]([c:8]1[c:2]([CH3:1])[cH:3][cH:4][c:5]([F:6])[cH:7]1)(=[O:11])=[O:12].[NH4+:10]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([F:6])[cH:7][c:8]1[S:9]([NH2:10])(=[O:11])=[O:12] | Cc1ccc(F)cc1S(=O)(=O)Cl.[NH4+] | Cc1ccc(F)cc1S(N)(=O)=O | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | 76fbc3582e2f63736dd65176b79ffad31881adfa34415872457e21307ad3c8dc | 8d9fe3486c870d18f12e4e21ee2410d7c9641745d38b34bc61fa11f384cef528 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH4+;D0:7]>>[NH2;D1;+0:7]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 98 | [{"value": 98.0, "product": "FC=1C=CC(=C(C1)S(=O)(=O)N)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-fluoro-2-methyl-benzenesulfonyl chloride (4.18 g, 20 mmol) in acetone (20 mL) was added, dropwise, concentrated NH4OH (3 mL) and the resulting mixture stirred for 5 min. Acetone was removed in vacuo and the precipitates were filtered, washed thoroughly with water and dried in vacuo to provide 3.7 g (... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | CC(=O)C | null | null | Cc1ccc(F)cc1S(=O)(=O)Cl.[NH4+]>CC(=O)C>Cc1ccc(F)cc1S(N)(=O)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-60bd8655d06b42f49624759eec58a5b2 | CI.Fc1ccc(Br)c(-c2nnn[nH]2)c1>>Cn1nnc(-c2cc(F)ccc2Br)n1 | BrC1=C(C=C(C=C1)F)C1=NN=NN1.IC.C([O-])([O-])=O.[K+].[K+]>>BrC1=C(C=C(C=C1)F)C=1N=NN(N1)C | I[CH3:1].[nH:2]1[c:5](-[c:6]2[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]2[Br:13])[n:4][n:3][n:14]1>>[CH3:1][n:2]1[n:3][n:4][c:5](-[c:6]2[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]2[Br:13])[n:14]1 | CI.Fc1ccc(Br)c(-c2nnn[nH]2)c1 | Cn1nnc(-c2cc(F)ccc2Br)n1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 930a6fb6aac3708578433b04494cf2b3154f49b6b8d322e37696a99afead7aa0 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ccc(-c2nn[nH]n2)cc1 | I-[CH3;D1;+0:1].[c:2]:[c:3](-[c;H0;D3;+0:4]1:[#7;a:5]:[n;H0;D2;+0:6]:[n;H0;D2;+0:7]:[nH;D2;+0:8]:1):[c:9]>>[CH3;D1;+0:1]-[n;H0;D3;+0:8]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:4](-[c:3](:[c:2]):[c:9]):[#7;a:5]:[n;H0;D2;+0:6]:1 | 61.4 | [{"value": 61.0, "product": "BrC1=C(C=C(C=C1)F)C=1N=NN(N1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.4, "product": "BrC1=C(C=C(C=C1)F)C=1N=NN(N1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture of 5-(2-bromo-5-fluoro-phenyl)-1H-tetrazole (1.0 g, 4.12 mmol), iodomethane (1.12 g, 10 mmol) and potassium carbonate (1.5 g) in dimethylformamide (5 mL) was stirred at room temperature for 16 hrs, then concentrated in vacuo. The residue was purified by column chromatography (SiO2, CH2Cl2) to provide 650 mg (... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1nnn[nH]1 | c1nnn[nH]1 | c1nnn[nH]1.c1ccccc1 | HI | CN(C=O)C | null | 16 | CI.Fc1ccc(Br)c(-c2nnn[nH]2)c1>CN(C=O)C>Cn1nnc(-c2cc(F)ccc2Br)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f797b4d64954af09da982c4095dd489 | Cn1nnc(-c2cc(F)ccc2Br)n1>>Cn1nnc(-c2cc(F)ccc2C#N)n1 | BrC1=C(C=C(C=C1)F)C=1N=NN(N1)C.C(#N)[Cu]>>FC1=CC(=C(C#N)C=C1)C=1N=NN(N1)C | Br[c:12]1[c:6](-[c:5]2[n:4][n:3][n:2]([CH3:1])[n:15]2)[cH:7][c:8]([F:9])[cH:10][cH:11]1>>[CH3:1][n:2]1[n:3][n:4][c:5](-[c:6]2[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]2[C:13]#[N:14])[n:15]1 | Cn1nnc(-c2cc(F)ccc2Br)n1 | Cn1nnc(-c2cc(F)ccc2C#N)n1 | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccc(-c2nn[nH]n2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]1:[#7;a:6]:[#7;a:7]:[#7;a:8]:[#7;a:9]:1):[c:10]>>[N;D1;H0:11]#[C:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]1:[#7;a:6]:[#7;a:7]:[#7;a:8]:[#7;a:9]:1):[c:10] | 73.8 | [{"value": 73.0, "product": "FC1=CC(=C(C#N)C=C1)C=1N=NN(N1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.8, "product": "FC1=CC(=C(C#N)C=C1)C=1N=NN(N1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | null | null | A mixture of intermediate 57, 5-(2-bromo-5-fluoro-phenyl)-2-methyl-2H-tetrazole (650 mg, 2.53 mmol) and CuCN (224 mg, 2.5 mmol) in dimethylformamide (4 mL) was placed in a sealed tube and heated at 100-110° C. for 20 hrs. After cooling, the insoluble material was filtered, and the filtrate concentrated in vacuo. The re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1nnn[nH]1.c1ccccc1 | Br- | CN(C=O)C | 105 | null | Cn1nnc(-c2cc(F)ccc2Br)n1>CN(C=O)C>Cn1nnc(-c2cc(F)ccc2C#N)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0524e42510cf4de0bc37d7d302c23ab4 | Cn1nnc(-c2cc(F)ccc2C#N)n1>>Cn1nnc(-c2cc(F)ccc2CN)n1 | FC1=CC(=C(C#N)C=C1)C=1N=NN(N1)C.Cl>>Cl.FC1=CC(=C(C=C1)CN)C=1N=NN(N1)C | [CH3:2][n:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]2[C:14]#[N:15])[n:16]1>>[CH3:2][n:3]1[n:4][n:5][c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]2[CH2:14][NH2:15])[n:16]1 | Cn1nnc(-c2cc(F)ccc2C#N)n1 | Cn1nnc(-c2cc(F)ccc2CN)n1 | null | [Pd] | C(C)O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(-c2nn[nH]n2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 91 | [{"value": 91.0, "product": "Cl.FC1=CC(=C(C=C1)CN)C=1N=NN(N1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of intermediate 58, 4-fluoro-2-(2-methyl-2H-tetrazol-5-yl)-benzonitrile, (330 mg, 1.62 mmol) in ethanol (15 mL) was mixed with 6N HCl (1 mL) and 10% Pd—C (200 mg) under nitrogen. The mixture was then stirred under hydrogen (1 atm) for 3 hrs. After removing the catalyst, the filtrate was concentrated in vacuo... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1nnn[nH]1.c1ccccc1 | null | [Pd].C(C)O | null | 3 | Cn1nnc(-c2cc(F)ccc2C#N)n1>[Pd].C(C)O>Cn1nnc(-c2cc(F)ccc2CN)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a773c69ff8624e18b0f51793686c325a | CI.Fc1ccc(Br)c(-c2nnn[nH]2)c1>>CN1NNN=C1c1cc(F)ccc1Br | BrC1=C(C=C(C=C1)F)C1=NN=NN1.IC.C([O-])([O-])=O.[K+].[K+]>>BrC1=C(C=C(C=C1)F)C1=NNNN1C | I[CH3:1].[nH:2]1[n:3][n:4][n:5][c:6]1-[c:7]1[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]1[Br:14]>>[CH3:1][N:2]1[NH:3][NH:4][N:5]=[C:6]1[c:7]1[cH:8][c:9]([F:10])[cH:11][cH:12][c:13]1[Br:14] | CI.Fc1ccc(Br)c(-c2nnn[nH]2)c1 | CN1NNN=C1c1cc(F)ccc1Br | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 9f40d716090edf274a06270f0173c4842a11dbd9d7197a72e036e8809b4a71b3 | 3d5ff1578c40ec948155ee63e26bcd44ed5627e79f81174ca8ffe0dd119c4dba | c1ccc(C2=NNNN2)cc1 | I-[CH3;D1;+0:1].[Br;D1;H0:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[n;H0;D2;+0:8]:[n;H0;D2;+0:9]:[nH;D2;+0:10]:1):[c:11]:[c:12]>>[Br;D1;H0:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[C;H0;D3;+0:6]1=[N;H0;D2;+0:7]-[NH;D2;+0:8]-[NH;D2;+0:9]-[N;H0;D3;+0:10]-1-[CH3;D1;+0:1]):[c:11]:[c:12] | 33 | [{"value": 33.0, "product": "BrC1=C(C=C(C=C1)F)C1=NNNN1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.8, "product": "BrC1=C(C=C(C=C1)F)C1=NNNN1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture of 5-(2-bromo-5-fluoro-phenyl)-1H-tetrazole (1.0 g, 4.12 mmol), iodomethane (1.12 g, 10 mmol) and potassium carbonate (1.5 g) in dimethylformamide (5 mL) was stirred at room temperature for 16 hrs, then concentrated in vacuo. The residue was purified by column chromatography (SiO2, CH2Cl2) to provide 350 mg (... | 10.6084/m9.figshare.5104873.v1 | null | null | Hydrazine.Hydrazine.Hydrazone | c1nnn[nH]1 | C1=NNN[NH]1 | C1=NNN[NH]1.c1ccccc1 | I- | CN(C=O)C | null | 16 | CI.Fc1ccc(Br)c(-c2nnn[nH]2)c1>CN(C=O)C>CN1NNN=C1c1cc(F)ccc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-81c87b1311544d9497322a7ff86f5b41 | Cc1cccc(C2(C(F)(F)F)NN2)c1>>Cc1cccc(C2(C(F)(F)F)N=N2)c1 | S(=O)([O-])[O-].[Na+].[Na+].C(C)N(CC)CC.C1(=CC(=CC=C1)C1(NN1)C(F)(F)F)C.ClOC(C)(C)C>>C1(=CC(=CC=C1)C1(N=N1)C(F)(F)F)C | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7]2([C:8]([F:9])([F:10])[F:11])[NH:12][NH:13]2)[cH:14]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7]2([C:8]([F:9])([F:10])[F:11])[N:12]=[N:13]2)[cH:14]1 | Cc1cccc(C2(C(F)(F)F)NN2)c1 | Cc1cccc(C2(C(F)(F)F)N=N2)c1 | null | null | C(C)O | Oxidation | OtherReaction | d4c1c5f2d88466e394c71fa23b4075bc66d1d54dd18a34ff41659f0abcd991a3 | af0c3c0cbdc6de6fea6137c38d32e5f7501ca840baaaf07cf656287a9aaca482 | c1ccc(C2N=N2)cc1 | [F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C:5]1(-[c:6])-[NH;D2;+0:7]-[NH;D2;+0:8]-1>>[F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C:5]1(-[c:6])-[N;H0;D2;+0:7]=[N;H0;D2;+0:8]-1 | 80 | [{"value": 80.0, "product": "C1(=CC(=CC=C1)C1(N=N1)C(F)(F)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a cold stirring solution of 3-m-tolyl-3-trifluoromethyl-diaziridine (2.0 g, 10 mmol. prepared using the methods described in Doucet-Personeni C. et al., J. Med. Chem., 2001, 44, 3203 and Nassal, M. Liebigs Ann. Chem. 1983, 1510-1523 or in Stromgaard, K et al., J. Med. Chem., 2002, 45, 4038-46) in ethanol (20 mL) was... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine | Diazene | C1NN1 | C1N=N1 | c1ccccc1.C1N=N1 | null | C(C)O | null | 0.083333 | Cc1cccc(C2(C(F)(F)F)NN2)c1>C(C)O>Cc1cccc(C2(C(F)(F)F)N=N2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7965cd4c675942eaa86bbab692b71822 | Cc1cccc(C2(C(F)(F)F)N=N2)c1.O=C1CCC(=O)N1Br>>FC(F)(F)C1(c2cccc(CBr)c2)N=N1 | CC(C)(C#N)N=NC(C)(C)C#N.C1(=CC(=CC=C1)C1(N=N1)C(F)(F)F)C.BrN1C(CCC1=O)=O>>BrCC=1C=C(C=CC1)C1(N=N1)C(F)(F)F | [F:1][C:2]([F:3])([F:4])[C:5]1([c:6]2[cH:7][cH:8][cH:9][c:10]([CH3:11])[cH:13]2)[N:14]=[N:15]1.O=C1CCC(=O)N1[Br:12]>>[F:1][C:2]([F:3])([F:4])[C:5]1([c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][Br:12])[cH:13]2)[N:14]=[N:15]1 | Cc1cccc(C2(C(F)(F)F)N=N2)c1.O=C1CCC(=O)N1Br | FC(F)(F)C1(c2cccc(CBr)c2)N=N1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc(C2N=N2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 54 | [{"value": 54.0, "product": "BrCC=1C=C(C=CC1)C1(N=N1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.8, "product": "BrCC=1C=C(C=CC1)C1(N=N1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | To a solution of intermediate 63, 3-m-tolyl-3-trifluoromethyl-3H-diazirine, (200 mg, 1 mmol) in CCl4 (4 mL) was added N-bromosuccinimide (200 mg, 1.1 mmol, re-crystallized from water), and the stirred mixture heated at 85° C. To this was added AIBN (50 mg) and the mixture heated at reflux for an additional 2.5 hrs. Aft... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1.C1N=N1 | HO- | C(Cl)(Cl)(Cl)Cl | 85 | null | Cc1cccc(C2(C(F)(F)F)N=N2)c1.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>FC(F)(F)C1(c2cccc(CBr)c2)N=N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-37b72579dd824e4e8d39d5470bd1b8ce | FC(F)(F)C1(c2cccc(CBr)c2)N=N1.O=C1NC(=O)c2ccccc21>>O=C1c2ccccc2C(=O)N1Cc1cccc(C2(C(F)(F)F)NN2)c1 | BrCC=1C=C(C=CC1)C1(N=N1)C(F)(F)F.C1(C=2C(C(N1)=O)=CC=CC2)=O.[K]>>FC(C1(NN1)C=1C=C(CN2C(C3=CC=CC=C3C2=O)=O)C=CC1)(F)F | Br[CH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]2([C:19]([F:20])([F:21])[F:22])[N:23]=[N:24]2)[cH:25]1.[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[NH:11]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]([C:18]2([C:19]([F:20])([F:21])... | FC(F)(F)C1(c2cccc(CBr)c2)N=N1.O=C1NC(=O)c2ccccc21 | O=C1c2ccccc2C(=O)N1Cc1cccc(C2(C(F)(F)F)NN2)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 4c865fab9d111ad9e304f11b498345c27f408e173c6a7bf6511a237bc5654553 | 8b90dd121a9459404c29e364a2a5e48a7f20b27e963729932413919d6eb85963 | O=C1c2ccccc2C(=O)N1Cc1cccc(C2NN2)c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]-[C:6]1(-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[F;D1;H0:10])-[N;H0;D2;+0:11]=[N;H0;D2;+0:12]-1.[O;D1;H0:13]=[C:14]1-[NH;D2;+0:15]-[C:16](=[O;D1;H0:17])-[c:18]:[c:19]-1>>[F;D1;H0:8]-[C:7](-[F;D1;H0:9])(-[F;D1;H0:10])-[C:6]1(-[c:5]:[c:4]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:15]2-[C:16](=... | 82 | [{"value": 82.0, "product": "FC(C1(NN1)C=1C=C(CN2C(C3=CC=CC=C3C2=O)=O)C=CC1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.6, "product": "FC(C1(NN1)C=1C=C(CN2C(C3=CC=CC=C3C2=O)=O)C=CC1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A mixture of intermediate 64, 3-(3-bromomethyl-phenyl)-3-trifluoromethyl-3H-diazirine, (140 mg, 0.5 mmol) and potassium phthalimide (95 mg, 0.5 mmol) in dimethylformamide (1.5 mL) was stirred at room temperature for 3 hrs. Dimethylformamide was removed in vacuo. The residue was extracted with CH2Cl2, washed with water,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Diazene.Unsubstituted dicarboximide | Hydrazine.Substituted dicarboximide | C1N=N1.c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2.C1NN1 | c1ccc2c(c1)C[NH]C2.c1ccccc1.C1NN1 | Br- | CN(C=O)C | null | 3 | FC(F)(F)C1(c2cccc(CBr)c2)N=N1.O=C1NC(=O)c2ccccc21>CN(C=O)C>O=C1c2ccccc2C(=O)N1Cc1cccc(C2(C(F)(F)F)NN2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aaa5aabaae534c5d815aeb623e07bc90 | O=C1c2ccccc2C(=O)N1Cc1cccc(C2(C(F)(F)F)NN2)c1>>NCc1cccc(C2(C(F)(F)F)NN2)c1 | FC(C1(NN1)C=1C=C(CN2C(C3=CC=CC=C3C2=O)=O)C=CC1)(F)F.O.NN.FC(C1(N=N1)C=1C=C(C=CC1)CN)(F)F>>FC(C1(NN1)C=1C=C(C=CC1)CN)(F)F | O=C1c2ccccc2C(=O)[N:1]1[CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8]2([C:9]([F:10])([F:11])[F:12])[NH:13][NH:14]2)[cH:15]1>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8]2([C:9]([F:10])([F:11])[F:12])[NH:13][NH:14]2)[cH:15]1 | O=C1c2ccccc2C(=O)N1Cc1cccc(C2(C(F)(F)F)NN2)c1 | NCc1cccc(C2(C(F)(F)F)NN2)c1 | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | c1ccc(C2NN2)cc1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[c:3])-C(=O)-c2:c:c:c:c:c:2-1>>[NH2;D1;+0:1]-[C:2]-[c:3] | 54 | [{"value": 54.0, "product": "FC(C1(NN1)C=1C=C(C=CC1)CN)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.5, "product": "FC(C1(NN1)C=1C=C(C=CC1)CN)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | A stirred solution of intermediate 65, 2-[3-(3-trifluoromethyl-diaziridin-3-yl)-benzyl]-isoindole-1,3-dione, (150 mg, 0.43 mmol) in ethanol (2 mL) was treated with hydrazine hydrate (0.4 mL) at room temperature and the solution stirred for 3.5 hrs. After removing ethanol in vacuo, the residue was partitioned between CH... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccccc1.C1NN1 | HO- | C(C)O | null | 3.5 | O=C1c2ccccc2C(=O)N1Cc1cccc(C2(C(F)(F)F)NN2)c1>C(C)O>NCc1cccc(C2(C(F)(F)F)NN2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea34a7e330bd406f98bf6c5b058cab7f | N#Cc1ccc(F)cc1-n1cncn1.NCc1ccc(F)cc1-n1cncn1>>N#Cc1ccc(-n2cncn2)cc1F | FC1=CC(=C(C#N)C=C1)N1N=CN=C1.Cl.Cl.FC1=CC(=C(C=C1)CN)N1N=CN=C1>>N1(N=CN=C1)C1=CC(=C(C#N)C=C1)F | c1ncn(-[c:13]2[c:3]([C:2]#[N:1])[cH:4][cH:5][c:6]([F:14])[cH:12]2)n1.NCc1ccc(F)cc1-[n:7]1[cH:8][n:9][cH:10][n:11]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[cH:8][n:9][cH:10][n:11]2)[cH:12][c:13]1[F:14] | N#Cc1ccc(F)cc1-n1cncn1.NCc1ccc(F)cc1-n1cncn1 | N#Cc1ccc(-n2cncn2)cc1F | null | [Pd] | C(C)O | Functional Group Interconversion | OtherReaction | 1f1872775e17cb8e244c6640d13c32fd86cc500cb3ea463805aab065e2391190 | 5f74ebbd0d40da38f38937c5d779c9d8b532f0902c1ada6a7de5154c23d802dd | c1ccc(-n2cncn2)cc1 | F-c1:c:c:c(-C-N):c(-[n;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:2):c:1.[F;H0;D1;+0:6]-[c;H0;D3;+0:7]1:[c:8]:[c;H0;D3;+0:9](-n2:c:n:c:n:2):[c:10](-[C:11]#[N;D1;H0:12]):[c:13]:[c:14]:1>>[F;H0;D1;+0:6]-[c;H0;D3;+0:9]1:[c:8]:[c;H0;D3;+0:7](-[n;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:2):[c:14]:[c:13]:[c:10]:1-[C:11]#[N... | 99 | [{"value": 99.0, "product": "N1(N=CN=C1)C1=CC(=C(C#N)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | (4-Fluoro-2-(1H-1,2,4-triazol-1-yl)phenyl)methanamine hydrochloride). Intermediate 67, 4-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile, (2.46 g, 13.13 mmol) was dissolved in hot ethanol (150 mL). To this was added 1N HCl (15 mL) followed by 10% Pd—C (200 mg). The mixture was treated with H2 at 55 psi for 4 h in a Parr s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Aromatic halide | c1nnc[nH]1.c1ccccc1.c1ccccc1.c1nc[nH]n1 | c1ccccc1.c1nc[nH]n1 | c1ccccc1.c1nc[nH]n1 | HF | [Pd].C(C)O | null | null | N#Cc1ccc(F)cc1-n1cncn1.NCc1ccc(F)cc1-n1cncn1>[Pd].C(C)O>N#Cc1ccc(-n2cncn2)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2f40c7874c25448d95e5a817868bbd87 | N#Cc1ccc(F)cc1N1CCCCS1(=O)=O>>NCc1ccc(F)cc1N1CCCCS1(=O)=O | FC1=CC(=C(C#N)C=C1)N1S(CCCC1)(=O)=O.Cl>>Cl.FC1=CC(=C(C=C1)CN)N1S(CCCC1)(=O)=O | [N:2]#[C:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]1[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][S:16]1(=[O:17])=[O:18]>>[NH2:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]1[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][S:16]1(=[O:17])=[O:18] | N#Cc1ccc(F)cc1N1CCCCS1(=O)=O | NCc1ccc(F)cc1N1CCCCS1(=O)=O | null | [Pd] | C(C)O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | O=S1(=O)CCCCN1c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 100 | [{"value": 100.0, "product": "Cl.FC1=CC(=C(C=C1)CN)N1S(CCCC1)(=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Intermediate 75, 4-fluoro-2-(1,1-dioxo-1λ6-[1,2]thiazinan-2-yl)benzonitrile (1.37 g, 5.4 mmol) was dissolved in ethanol (120 mL). To this was added 1N HCl (20 mL) and a catalytic amount of 10% Pd—C. The mixture was shaken under hydrogen at 55 psi for 4 h then filtered through Celite and concentrated to give the title c... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.C1CCS[NH]C1 | null | [Pd].C(C)O | null | 4 | N#Cc1ccc(F)cc1N1CCCCS1(=O)=O>[Pd].C(C)O>NCc1ccc(F)cc1N1CCCCS1(=O)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-506faeaea3484a76b0b18dc850a6b2c1 | N#Cc1ccc(F)cc1-n1nccn1>>NCc1ccc(F)cc1-n1nccn1 | Cl.FC1=CC(=C(C#N)C=C1)N1N=CC=N1>>Cl.FC1=CC(=C(CN)C=C1)N1N=CC=N1 | [N:2]#[C:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]1-[n:11]1[n:12][cH:13][cH:14][n:15]1>>[NH2:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]1-[n:11]1[n:12][cH:13][cH:14][n:15]1 | N#Cc1ccc(F)cc1-n1nccn1 | NCc1ccc(F)cc1-n1nccn1 | null | [Pd] | C(C)O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(-n2nccn2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 4 | HOUR | Intermediate 77, 4-fluoro-2-1,2,3-triazol-2-yl-benzonitrile, (0.34 g, 1.8 mmol) was dissolved in ethanol (50 mL). 1N HCl (10 mL) was added along with a catalytic amount of 10%-Pd—C. The mixture was shaken under H2 at 55 psi for 4 h after which it was filtered through Celite and concentrated to give the title compound a... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.c1c[nH]nn1 | null | [Pd].C(C)O | null | 4 | N#Cc1ccc(F)cc1-n1nccn1>[Pd].C(C)O>NCc1ccc(F)cc1-n1nccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-66586bd856364f78a42cba315020169c | N#Cc1ccc(F)cc1F.c1c[nH]cn1>>N#Cc1ccc(F)cc1-n1ccnc1 | N1C=NC=C1.C([O-])([O-])=O.[K+].[K+].FC1=C(C#N)C=CC(=C1)F>>FC1=CC(=C(C#N)C=C1)N1C=NC=C1 | F[c:9]1[c:3]([C:2]#[N:1])[cH:4][cH:5][c:6]([F:7])[cH:8]1.[nH:10]1[cH:11][cH:12][n:13][cH:14]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]1-[n:10]1[cH:11][cH:12][n:13][cH:14]1 | N#Cc1ccc(F)cc1F.c1c[nH]cn1 | N#Cc1ccc(F)cc1-n1ccnc1 | null | null | O1CCCC1.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | b282a5e1885a37e36f5b39b22cb06585a64583e50efbafa1ce368e9c3dbc55f3 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[#7;a:8]1:[c:9]:[c:10]:[nH;D2;+0:11]:[c:12]:1>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[n;H0;D3;+0:11]1:[c:10]:[c:9]:[#7;a:8]:[c:12]:1):[c:2]:[c:3] | 9 | [{"value": 9.0, "product": "FC1=CC(=C(C#N)C=C1)N1C=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 9.0, "product": "FC1=CC(=C(C#N)C=C1)N1C=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of imidazole (4.45 g, 65.4 mmol) in tetrahydrofuran (30 mL) and dimethylformamide (10 mL) was added potassium carbonate (9.95 g, 72 mmol) and the mixture was stirred for 30 min at room temp. To this was added 2,4-difluorobenzonitrile (10.0 g, 72 mmol) and the mixture stirred at 90° C. for 3 h then at room... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | HF | O1CCCC1.CN(C=O)C | null | 0.5 | N#Cc1ccc(F)cc1F.c1c[nH]cn1>O1CCCC1.CN(C=O)C>N#Cc1ccc(F)cc1-n1ccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-992c8966662e45b99992fe347fd506a7 | N#Cc1cc(F)ccc1F.c1nc[nH]n1>>N#Cc1cc(F)ccc1-n1cncn1 | FC1=C(C#N)C=C(C=C1)F.[Na].N1N=CN=C1>>FC=1C=CC(=C(C#N)C1)N1N=CN=C1 | F[c:9]1[c:3]([C:2]#[N:1])[cH:4][c:5]([F:6])[cH:7][cH:8]1.[nH:10]1[cH:11][n:12][cH:13][n:14]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1-[n:10]1[cH:11][n:12][cH:13][n:14]1 | N#Cc1cc(F)ccc1F.c1nc[nH]n1 | N#Cc1cc(F)ccc1-n1cncn1 | null | null | CN(C=O)C.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | dff1d318970a706943117b26793c51edded6a9a33120b190609ee0c5e3cf31e9 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2cncn2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[#7;a:8]1:[c:9]:[nH;D2;+0:10]:[#7;a:11]:[c:12]:1>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[c;H0;D3;+0:1](-[n;H0;D3;+0:10]1:[#7;a:11]:[c:12]:[#7;a:8]:[c:9]:1):[c:2]:[c:3] | 49 | [{"value": 49.0, "product": "FC=1C=CC(=C(C#N)C1)N1N=CN=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.0, "product": "FC=1C=CC(=C(C#N)C1)N1N=CN=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A suspension of 2,5-diflurobenzonitrile (4.5 g, 32.35 mmol) and 1,2,4-triazole sodium salt (3.6 g, 40 mmol) in dimethylformamide (40 mL) was heated at 80° C. for 15 h. The reaction mixture was then cooled, diluted with CH2Cl2 (200 mL), washed with water (3×30 mL) and brine (30 mL), then dried (Na2SO4), filtered and con... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1nc[nH]n1 | c1ccccc1.c1nc[nH]n1 | c1ccccc1.c1nc[nH]n1 | HF | CN(C=O)C.C(Cl)Cl | 80 | null | N#Cc1cc(F)ccc1F.c1nc[nH]n1>CN(C=O)C.C(Cl)Cl>N#Cc1cc(F)ccc1-n1cncn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1a4f8e5372a424cab5cc30d6f794e58 | N#Cc1cc(F)ccc1-n1cncn1>>NCc1cc(F)ccc1-n1cncn1 | FC=1C=CC(=C(C#N)C1)N1N=CN=C1.Cl>>Cl.FC=1C=CC(=C(C1)CN)N1N=CN=C1 | [N:2]#[C:3][c:4]1[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]1-[n:11]1[cH:12][n:13][cH:14][n:15]1>>[NH2:2][CH2:3][c:4]1[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]1-[n:11]1[cH:12][n:13][cH:14][n:15]1 | N#Cc1cc(F)ccc1-n1cncn1 | NCc1cc(F)ccc1-n1cncn1 | null | null | C(C)O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(-n2cncn2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 98 | [{"value": 98.0, "product": "Cl.FC=1C=CC(=C(C1)CN)N1N=CN=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | A solution of intermediate 96, 5-fluoro-2-(1H-1,2,4-triazol-1-yl)benzonitrile (2.94 g, 15.59 mmol) in ethanol (100 mL) and 1N HCl (50 mL) was degassed by bubbling N2. Then, 10%Pd/C was added, the flask evacuated and vented to H2 three times and left on a Parr shaker under a H2 atmosphere (40 psi). After 6 h, the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.c1nc[nH]n1 | null | C(C)O | null | 6 | N#Cc1cc(F)ccc1-n1cncn1>C(C)O>NCc1cc(F)ccc1-n1cncn1 |
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