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-c3a75813d0b24864aa4f7cd526efd6aa | ord-49ca91ad7fb74f988528f46bcedfda07 | Cc1ccc(OS(=O)(=O)c2cccc(NS(=O)(=O)c3cc(O)c4ccc(NC(=O)Nc5ccc6c(O)cc(S(=O)(=O)Nc7cccc(S(=O)(=O)Oc8ccc(C)cc8)c7)cc6c5)cc4c3)c2)cc1.O=C(Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.O=C(Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1>>O=C(Nc1ccc2c(O)cc(S(=O)(=... | OC1=CC(=CC2=CC(=CC=C12)NC(NC1=CC2=CC(=CC(=C2C=C1)O)S(=O)(=O)NC1=CC(=CC=C1)S(=O)(=O)OC1=CC=C(C=C1)C)=O)S(=O)(=O)NC=1C=C(C=CC1)S(=O)(=O)OC1=CC=C(C=C1)C.[Na+].[Na+].S(=O)(=O)(O)C=1C=C(C=CC1)NS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NC(=O)NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)[O-].S(=O)(=O)(O)C=1C=C(C=CC1)NS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NC(=... | Cc1ccc(O[S:21]([c:20]2[cH:19][cH:18][cH:17][c:16]([NH:15][S:12]([c:11]3[cH:10][c:8]([OH:9])[c:7]4[cH:6][cH:5][c:4]([NH:3][C:2](=[O:1])[NH:29][c:30]5[cH:31][cH:32][c:33]6[c:34]([OH:35])[cH:36][c:37]([S:38](=[O:39])(=[O:40])[NH:41][c:42]7[cH:43][cH:44][cH:45][c:46]([S:47](Oc8ccc(C)cc8)(=[O:48])=[O:49])[cH:51]7)[cH:52][c:... | Cc1ccc(OS(=O)(=O)c2cccc(NS(=O)(=O)c3cc(O)c4ccc(NC(=O)Nc5ccc6c(O)cc(S(=O)(=O)Nc7cccc(S(=O)(=O)Oc8ccc(C)cc8)c7)cc6c5)cc4c3)c2)cc1.O=C(Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.O=C(Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1 | O=C(Nc1ccc2c(O)cc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1)Nc1ccc2c(O)cc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1 | null | null | null | Miscellaneous | OtherReaction | c44a3d0b1866e40b32c9c79793b8c42ba731fb8965ea70b5cd359af8a1546910 | 32cc1167ae83b7e02af505f483839c787441349f55b7abb28acc9a9bb101c437 | O=C(Nc1ccc2ccc(S(=O)(=O)Nc3ccccc3)cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3ccccc3)cc2c1 | C-c1:c:c:c(-O-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]):c:c:1.C-c1:c:c:c(-O-[S;H0;D4;+0:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10](:[c:11]):[c:12]):c:c:1.O=C(-N-c1:c:c:c2:c:c:c(-S(=O)(=O)-[O-]):c:c:2:c:1)-N-c1:c:c:c2:c:c:c(-S(=O)(=O)-N-c3:c:c:c:c(-S(=O)(=O)-[OH;D1;+0:13]):c:3):c:c:2:c:1.O=C(-N-c1:c:c:c... | null | [] | null | null | null | null | This compound was prepared from compound 11 according to the procedure described for the synthesis of compound 12.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Sulfonamide.Urea.Urea.Sulfonic acid.Sulfonic acid.Sulfonic acid.Sulfonic acid.Sulfonate.Sulfonate | Sulfonic acid.Sulfonic acid | c1ccccc1.c1ccccc1.c1ccc2ccccc2c1.c1ccc2ccccc2c1.c1ccccc1.c1ccc2ccccc2c1.c1ccc2ccccc2c1.c1ccccc1 | null | c1ccc2ccccc2c1.c1ccccc1.c1ccc2ccccc2c1.c1ccccc1 | HO- | null | null | null | Cc1ccc(OS(=O)(=O)c2cccc(NS(=O)(=O)c3cc(O)c4ccc(NC(=O)Nc5ccc6c(O)cc(S(=O)(=O)Nc7cccc(S(=O)(=O)Oc8ccc(C)cc8)c7)cc6c5)cc4c3)c2)cc1.O=C(Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.O=C(Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1>>O=C(Nc1ccc2c(O)cc(S(=O)(=... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4cfc17a8dc7541c4a99b863a0fe071df | CCOC(=O)COc1cc(S(=O)(=O)O)cc2cc(NC(=O)Nc3ccc4c(O)cc(S(=O)(=O)[O-])cc4c3)ccc12.CCOC(=O)COc1cc(S(=O)(=O)O)cc2cc(NC(=O)Nc3ccc4c(O)cc(S(=O)(=O)[O-])cc4c3)ccc12>>O=C([O-])COc1cc(S(=O)(=O)O)cc2cc(NC(=O)Nc3ccc4c(O)cc(S(=O)(=O)O)cc4c3)ccc12.O=C([O-])COc1cc(S(=O)(=O)O)cc2cc(NC(=O)Nc3ccc4c(O)cc(S(=O)(=O)O)cc4c3)ccc12.[Na+] | [NH4+].[NH4+].C(C)OC(=O)COC1=C2C=CC(=CC2=CC(=C1)S(=O)(=O)O)NC(=O)NC1=CC=C2C(=CC(=CC2=C1)S(=O)(=O)[O-])O.C(C)OC(=O)COC1=C2C=CC(=CC2=CC(=C1)S(=O)(=O)O)NC(=O)NC1=CC=C2C(=CC(=CC2=C1)S(=O)(=O)[O-])O.[OH-].[Na+].Cl>>[Na+].[Na+].OC1=C2C=CC(=CC2=CC(=C1)S(=O)(=O)O)NC(=O)NC=1C=C2C=C(C=C(C2=CC1)OCC(=O)[O-])S(=O)(=O)O.OC1=C2C=CC(=... | CC[O:3][C:2](=[O:1])[CH2:4][O:5][c:6]1[cH:7][c:8]([S:9](=[O:10])(=[O:11])[OH:12])[cH:13][c:14]2[cH:15][c:16]([NH:17][C:18](=[O:19])[NH:20][c:21]3[cH:22][cH:23][c:24]4[c:25]([OH:26])[cH:27][c:28]([S:29](=[O:30])(=[O:31])[O-:32])[cH:33][c:34]4[cH:35]3)[cH:36][cH:37][c:38]12.CC[O:41][C:40](=[O:39])[CH2:42][O:43][c:44]1[cH... | CCOC(=O)COc1cc(S(=O)(=O)O)cc2cc(NC(=O)Nc3ccc4c(O)cc(S(=O)(=O)[O-])cc4c3)ccc12.CCOC(=O)COc1cc(S(=O)(=O)O)cc2cc(NC(=O)Nc3ccc4c(O)cc(S(=O)(=O)[O-])cc4c3)ccc12 | O=C([O-])COc1cc(S(=O)(=O)O)cc2cc(NC(=O)Nc3ccc4c(O)cc(S(=O)(=O)O)cc4c3)ccc12.O=C([O-])COc1cc(S(=O)(=O)O)cc2cc(NC(=O)Nc3ccc4c(O)cc(S(=O)(=O)O)cc4c3)ccc12.[Na+] | null | null | null | Miscellaneous | OtherReaction | ad25e0e38e4e58ba7eaff41ed26f52321618d1a7f9a5e5ce366a94e912478d84 | ec1b4cbc36c81a2bdcb1853a9605a22897489bd540e9dce16dea81e87307b9cf | O=C(Nc1ccc2ccccc2c1)Nc1ccc2ccccc2c1.O=C(Nc1ccc2ccccc2c1)Nc1ccc2ccccc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[O-;H0;D1:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9].C-C-[O;H0;D2;+0:10]-[C:11](-[C:12])=[O;D1;H0:13].[O-;H0;D1:14]-[#16:15](=[O;D1;H0:16])(=[O;D1;H0:17])-[c:18]>>[C:3]-[C:2](-[O-;H0;D1:1])=[O;D1;H0:4].[O;D1;H0:7]=[#16:6](=[O;D1;H0:8])(-[OH;D1;+0:5])-[c:9].[C:12]-[C:11](-[... | null | [] | null | null | 18 | HOUR | To 25 mg (0.04 mmol) of compound 94 was added 1 mL of 5 N NaOH. The solution was allowed to stir for 18 hours at ambient temperature. The pH was lowered to 1 with aqueous HCl and the resulting solid was collected by vacuum filtration to afford 16 mg of compound 96.
Conditions: See reaction.notes.procedure_details.
Work... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | null | null | null | c1ccc2ccccc2c1.c1ccc2ccccc2c1.c1ccc2ccccc2c1.c1ccc2ccccc2c1 | Other | null | null | 18 | CCOC(=O)COc1cc(S(=O)(=O)O)cc2cc(NC(=O)Nc3ccc4c(O)cc(S(=O)(=O)[O-])cc4c3)ccc12.CCOC(=O)COc1cc(S(=O)(=O)O)cc2cc(NC(=O)Nc3ccc4c(O)cc(S(=O)(=O)[O-])cc4c3)ccc12>>O=C([O-])COc1cc(S(=O)(=O)O)cc2cc(NC(=O)Nc3ccc4c(O)cc(S(=O)(=O)O)cc4c3)ccc12.O=C([O-])COc1cc(S(=O)(=O)O)cc2cc(NC(=O)Nc3ccc4c(O)cc(S(=O)(=O)O)cc4c3)ccc12.[Na+] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-86d1c4f394a0491a9858d47adc5f5943 | C1CCOC1.C[O-].Cc1ccc(OS(=O)(=O)c2cccc(NS(=O)(=O)c3ccc4ccc(NC(=O)Nc5ccc6ccc(S(=O)(=O)Nc7cccc(S(=O)(=O)Oc8ccc(C)cc8)c7)cc6c5)cc4c3)c2)cc1>>O=C(Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)[O-])c3)cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.O=C(Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)[O-])c3)cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cc... | CC1=CC=C(C=C1)OS(=O)(=O)C=1C=C(C=CC1)NS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NC(=O)NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)NC=1C=C(C=CC1)S(=O)(=O)OC1=CC=C(C=C1)C.C[O-].[Na+].C1CCOC1.Cl>>[Na+].[Na+].S(=O)(=O)(O)C=1C=C(C=CC1)NS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NC(=O)NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)NC=1C=C(C=CC1)S(=O)(=O)[O-].S(=O)(=O)(O)C=1C=C(... | [CH2:4]1[O:21][CH2:49][CH2:44][CH2:43]1.[O-:23][CH3:34].[O:1]=[C:2]([NH:3][c:81]1[cH:82][cH:83][c:84]2[cH:85][cH:86][c:87]([S:88](=[O:48])(=[O:89])[NH:91][c:92]3[cH:93][cH:94][cH:95][c:96]([S:97](=[O:98])(=[O:99])[O:100][c:29]4[cH:30][cH:31][c:32]([CH3:33])[cH:51][cH:52]4)[cH:101]3)[cH:102][c:103]2[cH:104]1)[NH:55][c:5... | C1CCOC1.C[O-].Cc1ccc(OS(=O)(=O)c2cccc(NS(=O)(=O)c3ccc4ccc(NC(=O)Nc5ccc6ccc(S(=O)(=O)Nc7cccc(S(=O)(=O)Oc8ccc(C)cc8)c7)cc6c5)cc4c3)c2)cc1 | O=C(Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)[O-])c3)cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.O=C(Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)[O-])c3)cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.[Na+] | null | null | O.CO | Aromatic Heterocycle Formation | OtherReaction | 7a4728662244d3bd6da1991adcfb1701cd456ffa004cbf91cf978bfdaae74315 | 25840246cb850879fc4eb85689e90207f001fb9320606401c2271a44acad0c96 | O=C(Nc1ccc2ccc(S(=O)(=O)Nc3ccccc3)cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3ccccc3)cc2c1.O=C(Nc1ccc2ccc(S(=O)(=O)Nc3ccccc3)cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3ccccc3)cc2c1 | [CH2;D2;+0:1]1-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-[CH2;D2;+0:5]-1.[CH3;D1;+0:6]-[O-;H0;D1:7].[CH3;D1;+0:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[c:11]:[c;H0;D3;+0:12](-[O;H0;D2;+0:13]-[#16:14](=[O;D1;H0:15])(=[O;D1;H0:16])-[c:17]:[c:18]:[c:19](-[NH;D2;+0:20]-[S;H0;D4;+0:21](=[O;D1;H0:22])(=[O;D1;H0:23])-[c;H0;D3;+0:24... | null | [] | null | null | 2 | DAY | To 20 mg (0.02 mole) of compound 112 was added 1.5 mL of 1.37 M sodium methoxide in methanol, 1 mL of water, and 0.5 mL of THF. The resulting solution was allowed to stir at ambient temperature for 2 days. The reaction was acidified with 1 N HCl (aqueous) and the organic volatiles removed in vacuo. The solid precipitat... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Sulfonamide.Ether.Urea | Sulfonamide.Sulfonamide.Sulfonamide.Sulfonamide.Urea.Urea.Sulfonic acid.Sulfonic acid | C1CCOC1.c1ccc2ccccc2c1.c1ccccc1.c1ccc2ccccc2c1.c1ccccc1 | c1ccc2ccccc2c1.c1ccccc1.c1ccc2ccccc2c1.c1ccccc1.c1ccc2ccccc2c1.c1ccc2ccccc2c1 | c1ccc2ccccc2c1.c1ccccc1.c1ccc2ccccc2c1.c1ccccc1.c1ccc2ccccc2c1.c1ccccc1.c1ccc2ccccc2c1.c1ccccc1 | null | O.CO | null | 48 | C1CCOC1.C[O-].Cc1ccc(OS(=O)(=O)c2cccc(NS(=O)(=O)c3ccc4ccc(NC(=O)Nc5ccc6ccc(S(=O)(=O)Nc7cccc(S(=O)(=O)Oc8ccc(C)cc8)c7)cc6c5)cc4c3)c2)cc1>O.CO>O=C(Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)[O-])c3)cc2c1)Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)O)c3)cc2c1.O=C(Nc1ccc2ccc(S(=O)(=O)Nc3cccc(S(=O)(=O)[O-])c3)cc2c1)Nc1ccc2ccc(S(=O)(=O)N... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b083c6100e4b4eea844e4ac00200b6b7 | COC(=O)c1cccc(NC(=O)c2ccc3ccc(NC(=O)OCC4c5ccccc5-c5ccccc54)cc3c2)c1>>COC(=O)c1cccc(NC(=O)c2ccc3ccc(N)cc3c2)c1 | C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)NC1=CC=C2C=CC(=CC2=C1)C(=O)NC=1C=C(C(=O)OC)C=CC1.ClCCl.N1CCCCC1>>NC1=CC=C2C=CC(=CC2=C1)C(=O)NC=1C=C(C(=O)OC)C=CC1 | O=C(OCC1c2ccccc2-c2ccccc21)[NH:20][c:19]1[cH:18][cH:17][c:16]2[cH:15][cH:14][c:13]([C:11]([NH:10][c:9]3[cH:8][cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:24]3)=[O:12])[cH:23][c:22]2[cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([NH:10][C:11](=[O:12])[c:13]2[cH:14][cH:15][c:16]3[cH:17][cH:18][c:19](... | COC(=O)c1cccc(NC(=O)c2ccc3ccc(NC(=O)OCC4c5ccccc5-c5ccccc54)cc3c2)c1 | COC(=O)c1cccc(NC(=O)c2ccc3ccc(N)cc3c2)c1 | null | null | C1CCOC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 6b8c76d50ec667b483b13f7e325104eed6ba06fddb821da46e405c5dce0a3de5 | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=C(Nc1ccccc1)c1ccc2ccccc2c1 | O=C(-O-C-C1-c2:c:c:c:c:c:2-c2:c:c:c:c:c:2-1)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 3 | HOUR | To 380 mg (0.70 mmol) of compound 109 was added 30 mL of dichloromethane, 3 mL of THF and 1 mL of piperidine. The resulting clear solution was allowed to stir for 3 hours. Then, the reaction was extracted with ethyl acetate and 1N HCl (aqueous). The dried organic layer (magnesium sulfate) was filtered and the volatiles... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccc2c(c1)Cc1ccccc12 | null | c1ccccc1.c1ccc2ccccc2c1 | HO- | C1CCOC1 | null | 3 | COC(=O)c1cccc(NC(=O)c2ccc3ccc(NC(=O)OCC4c5ccccc5-c5ccccc54)cc3c2)c1>C1CCOC1>COC(=O)c1cccc(NC(=O)c2ccc3ccc(N)cc3c2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e6ec6444e7a244958e2f3cc3d981ef0a | C1CCOC1.C1CCOC1.COC(=O)c1cccc(NC(=O)c2ccc3ccc(N)cc3c2)c1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.[OH-]>>COC(=O)c1cccc(NC(=O)c2ccc3ccc(NC(=O)Nc4ccc5ccc(C(=O)Nc6cccc(C(=O)OC)c6)cc5c4)cc3c2)c1 | ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl.Cl.C1CCOC1.[OH-].[Na+].NC1=CC=C2C=CC(=CC2=C1)C(=O)NC=1C=C(C(=O)OC)C=CC1.C1CCOC1>>COC(=O)C=1C=C(C=CC1)NC(=O)C1=CC=C2C=CC(=CC2=C1)NC(=O)NC1=CC=C2C=CC(=CC2=C1)C(=O)NC=1C=C(C(=O)OC)C=CC1 | O1[CH2:1][CH2:13][CH2:49][CH2:48]1.O1[CH2:14][CH2:15][CH2:16][CH2:17]1.[NH2:10][c:24]1[cH:25][cH:26][c:27]2[cH:28][cH:29][c:30]([C:31](=[O:32])[NH:33][c:34]3[cH:35][cH:36][cH:37][c:38]([C:39](=[O:40])[O:41][CH3:42])[cH:43]3)[cH:44][c:45]2[cH:46]1.Cl[C:3](Cl)(Cl)[O:4][C:11](=[O:12])[O:22][C:21](Cl)(Cl)Cl.[OH-:2]>>[CH3:1... | C1CCOC1.C1CCOC1.COC(=O)c1cccc(NC(=O)c2ccc3ccc(N)cc3c2)c1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.[OH-] | COC(=O)c1cccc(NC(=O)c2ccc3ccc(NC(=O)Nc4ccc5ccc(C(=O)Nc6cccc(C(=O)OC)c6)cc5c4)cc3c2)c1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | c604bf4ebdd9e9af936096f0053cc06d1765174d984485c15795ce1d53372706 | 6fcb91a2a6fb3baf2ecbeefdfa36091cbf862720f91bfd944f9fc330b353dd47 | O=C(Nc1ccc2ccc(C(=O)Nc3ccccc3)cc2c1)Nc1ccc2ccc(C(=O)Nc3ccccc3)cc2c1 | Cl-[C;H0;D4;+0:1](-Cl)(-Cl)-[O;H0;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[C;H0;D4;+0:6](-Cl)(-Cl)-Cl.O1-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-1.O1-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[CH2;D2;+0:13]-[CH2;D2;+0:14]-1.[NH2;D1;+0:15]-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:19]:[c:20].[OH-;D0:21]>>[CH3... | null | [] | null | null | null | null | To 21 mg (0.07 mmol) of compound 111 dissolved in 2 mL of THF and 1 mL of water was added, portionwise and alternating, a solution of 112 μL of 5 N NaOH (aqueous) in 1 mL of water followed by a solution of 28 mg (0.10 mmol) of triphosgene in 1 mL of THF. The reaction was acidified with 1N HCl and the volatiles were rem... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Ether.Ether.Primary amine | Ester.Urea.Secondary amide | C1CCOC1.C1CCOC1.c1ccc2ccccc2c1 | c1ccccc1.c1ccc2ccccc2c1.c1ccc2ccccc2c1 | c1ccccc1.c1ccc2ccccc2c1.c1ccc2ccccc2c1.c1ccccc1 | HCl | O | null | null | C1CCOC1.C1CCOC1.COC(=O)c1cccc(NC(=O)c2ccc3ccc(N)cc3c2)c1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.[OH-]>O>COC(=O)c1cccc(NC(=O)c2ccc3ccc(NC(=O)Nc4ccc5ccc(C(=O)Nc6cccc(C(=O)OC)c6)cc5c4)cc3c2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f9be0e01620342b8a8afc6d51c128097 | COC(=O)c1cccc(NC(=O)c2ccc3ccc(N)cc3c2)c1>>Nc1ccc2ccc(C(=O)Nc3cccc(C(=O)O)c3)cc2c1 | Cl.NC1=CC=C2C=CC(=CC2=C1)C(=O)NC=1C=C(C(=O)OC)C=CC1.CO.[OH-].[Li+]>>NC1=CC=C2C=CC(=CC2=C1)C(=O)NC=1C=C(C(=O)O)C=CC1 | C[O:19][C:17]([c:16]1[cH:15][cH:14][cH:13][c:12]([NH:11][C:9]([c:8]2[cH:7][cH:6][c:5]3[cH:4][cH:3][c:2]([NH2:1])[cH:23][c:22]3[cH:21]2)=[O:10])[cH:20]1)=[O:18]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][c:8]([C:9](=[O:10])[NH:11][c:12]3[cH:13][cH:14][cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20]3)[cH:21][c:22]2[cH:23]1 | COC(=O)c1cccc(NC(=O)c2ccc3ccc(N)cc3c2)c1 | Nc1ccc2ccc(C(=O)Nc3cccc(C(=O)O)c3)cc2c1 | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1ccccc1)c1ccc2ccccc2c1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 16 | HOUR | To 51 mg (0.16 mmol) of compound 111 was added 1 mL of methanol. 1 mL of water, and 800 μL of 1N lithium hydroxide (aqueous). The reaction was allowed to stir for 16 hours at ambient temperature. The pH of the solution was lowered to 3 with 1N HCl (aqueous) and the volatiles removed in vacuo. The resulting solid was su... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2ccccc2c1.c1ccccc1 | Other | O | null | 16 | COC(=O)c1cccc(NC(=O)c2ccc3ccc(N)cc3c2)c1>O>Nc1ccc2ccc(C(=O)Nc3cccc(C(=O)O)c3)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-afc33c74768f48aca0a7160392b544d4 | C1CCOC1.C1CCOC1.Nc1ccc2ccc(C(=O)Nc3cccc(C(=O)O)c3)cc2c1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.[OH-]>>O=C(Nc1ccc2ccc(C(=O)Nc3cccc(C(=O)O)c3)cc2c1)Nc1ccc2ccc(C(=O)Nc3cccc(C(=O)O)c3)cc2c1 | ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl.Cl.C1CCOC1.[OH-].[Na+].NC1=CC=C2C=CC(=CC2=C1)C(=O)NC=1C=C(C(=O)O)C=CC1.C1CCOC1>>C(=O)(O)C=1C=C(C=CC1)NC(=O)C1=CC=C2C=CC(=CC2=C1)NC(=O)NC1=CC=C2C=CC(=CC2=C1)C(=O)NC=1C=C(C(=O)O)C=CC1 | O1[CH2:39][CH2:40][CH2:41][CH2:45]1.O1[CH2:27][CH2:47][CH2:30][CH2:33]1.[NH2:3][c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][c:10]([C:11](=[O:12])[NH:13][c:14]3[cH:15][cH:16][cH:17][c:18]([C:19](=[O:20])[OH:21])[cH:22]3)[cH:23][c:24]2[cH:25]1.Cl[C:2](Cl)(Cl)[O:1][C:34](=[O:35])[O:44][C:42](Cl)(Cl)Cl.[OH-:43]>>[O:1]=[C:2]([NH:3]... | C1CCOC1.C1CCOC1.Nc1ccc2ccc(C(=O)Nc3cccc(C(=O)O)c3)cc2c1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.[OH-] | O=C(Nc1ccc2ccc(C(=O)Nc3cccc(C(=O)O)c3)cc2c1)Nc1ccc2ccc(C(=O)Nc3cccc(C(=O)O)c3)cc2c1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 8b0ba0ec828b3ada75eee1377f3d7c0b11ee612c1f1ed34e7829a7bf2cce5d7b | 368e32562919214ae4654aba521d118fd5b472b75e028b786b52c27fe9f10e35 | O=C(Nc1ccc2ccc(C(=O)Nc3ccccc3)cc2c1)Nc1ccc2ccc(C(=O)Nc3ccccc3)cc2c1 | Cl-[C;H0;D4;+0:1](-Cl)(-Cl)-[O;H0;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[C;H0;D4;+0:6](-Cl)(-Cl)-Cl.O1-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-1.O1-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[CH2;D2;+0:13]-[CH2;D2;+0:14]-1.[NH2;D1;+0:15]-[c:16](:[c:17]):[c:18].[OH-;D0:19]>>[O;D1;H0:4]=[C;H0;D3;+0:3](... | null | [] | null | null | null | null | To 10 mg (0.03 mmol) of compound 115 dissolved in 2 mL of THF and 1 mL of water was added, portionwise and alternating, a solution of 40 μL of 5 N NaOH (aqueous) in 0.2 mL of water followed by a solution of 4 mg (0.02 mmol) of triphosgene in 0.2 mL of THF. The reaction was acidified with 1N HCl and the volatiles were r... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Ether.Ether.Primary amine | Carboxylic acid.Urea.Secondary amide | C1CCOC1.C1CCOC1 | c1ccc2ccccc2c1.c1ccccc1 | c1ccc2ccccc2c1.c1ccccc1.c1ccc2ccccc2c1.c1ccccc1 | HCl | O | null | null | C1CCOC1.C1CCOC1.Nc1ccc2ccc(C(=O)Nc3cccc(C(=O)O)c3)cc2c1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.[OH-]>O>O=C(Nc1ccc2ccc(C(=O)Nc3cccc(C(=O)O)c3)cc2c1)Nc1ccc2ccc(C(=O)Nc3cccc(C(=O)O)c3)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9ca64eda72ed45958f0f229fc7b46a78 | COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(NCCNc4ccc5ccc(S(=O)(=O)Nc6ccc(O)c(C(=O)OC)c6)cc5c4)cc3c2)ccc1O>>O=C(O)c1cc(NS(=O)(=O)c2ccc3ccc(NCCNc4ccc5ccc(S(=O)(=O)Nc6ccc(O)c(C(=O)O)c6)cc5c4)cc3c2)ccc1O | OC1=C(C(=O)OC)C=C(C=C1)NS(=O)(=O)C1=CC2=CC(=CC=C2C=C1)NCCNC1=CC2=CC(=CC=C2C=C1)S(=O)(=O)NC1=CC(=C(C=C1)O)C(=O)OC.C([O-])([O-])=O.[Na+].[Na+].S(=O)([O-])S(=O)[O-].[Na+].[Na+]>>C(=O)(O)C=1C=C(C=CC1O)NS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NCCNC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)NC=1C=CC(=C(C(=O)O)C1)O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][c:6]([NH:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][c:14]3[cH:15][cH:16][c:17]([NH:18][CH2:19][CH2:20][NH:21][c:22]4[cH:23][cH:24][c:25]5[cH:26][cH:27][c:28]([S:29](=[O:30])(=[O:31])[NH:32][c:33]6[cH:34][cH:35][c:36]([OH:37])[c:38]([C:39](=[O:40])[O:41]C)[cH:42]6)[cH:43][c:44]5[cH:45]... | COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(NCCNc4ccc5ccc(S(=O)(=O)Nc6ccc(O)c(C(=O)OC)c6)cc5c4)cc3c2)ccc1O | O=C(O)c1cc(NS(=O)(=O)c2ccc3ccc(NCCNc4ccc5ccc(S(=O)(=O)Nc6ccc(O)c(C(=O)O)c6)cc5c4)cc3c2)ccc1O | null | null | CN(C)C=O | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | O=S(=O)(Nc1ccccc1)c1ccc2ccc(NCCNc3ccc4ccc(S(=O)(=O)Nc5ccccc5)cc4c3)cc2c1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4].[O;D1;H0:7]=[C:6](-[OH;D1;+0:5])-[c:8] | 40.4 | [{"value": 40.4, "product": "C(=O)(O)C=1C=C(C=CC1O)NS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NCCNC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)NC=1C=CC(=C(C(=O)O)C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 22 | HOUR | To 64 mg (0.08 mmol) of compound 120 was added 20 mL of saturated sodium carbonate, 76 mg of sodium hydrosulfite (Na2S2O4), and 2 mL of DMF. The reaction was allowed to stir at ambient temperature for 22 hours. Then, the reaction was extracted with ethyl acetate and 1 N HCl. The organic layer was dried (MgSO4), filtere... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1.c1ccc2ccccc2c1.c1ccc2ccccc2c1.c1ccccc1 | Other | CN(C)C=O | null | 22 | COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(NCCNc4ccc5ccc(S(=O)(=O)Nc6ccc(O)c(C(=O)OC)c6)cc5c4)cc3c2)ccc1O>CN(C)C=O>O=C(O)c1cc(NS(=O)(=O)c2ccc3ccc(NCCNc4ccc5ccc(S(=O)(=O)Nc6ccc(O)c(C(=O)O)c6)cc5c4)cc3c2)ccc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-85a8945eb96d4f8b9bad61099a78bf93 | O=C(O)c1cc(NS(=O)(=O)c2ccc3ccc(NCCNc4ccc5ccc(S(=O)(=O)Nc6ccc(O)c(C(=O)O)c6)cc5c4)cc3c2)ccc1O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>O=C(O)c1cc(NS(=O)(=O)c2ccc3ccc(N4CCN(c5ccc6ccc(S(=O)(=O)Nc7ccc(O)c(C(=O)O)c7)cc6c5)C4=O)cc3c2)ccc1O | Cl.ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl.C(=O)(O)C=1C=C(C=CC1O)NS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NCCNC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)NC=1C=CC(=C(C(=O)O)C1)O.ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl>>C(=O)(O)C=1C=C(C=CC1O)NS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)N1C(N(CC1)C1=CC=C2C=CC(=CC2=C1)S(=O)(=O)NC=1C=CC(=C(C(=O)O)C1)O)=O | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH:7][S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][c:14]3[cH:15][cH:16][c:17]([NH:18][CH2:19][CH2:20][NH:21][c:22]4[cH:23][cH:24][c:25]5[cH:26][cH:27][c:28]([S:29](=[O:30])(=[O:31])[NH:32][c:33]6[cH:34][cH:35][c:36]([OH:37])[c:38]([C:39](=[O:40])[OH:41])[cH:42]6)[cH:43][c:44]5[cH:45]... | O=C(O)c1cc(NS(=O)(=O)c2ccc3ccc(NCCNc4ccc5ccc(S(=O)(=O)Nc6ccc(O)c(C(=O)O)c6)cc5c4)cc3c2)ccc1O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | O=C(O)c1cc(NS(=O)(=O)c2ccc3ccc(N4CCN(c5ccc6ccc(S(=O)(=O)Nc7ccc(O)c(C(=O)O)c7)cc6c5)C4=O)cc3c2)ccc1O | null | null | O.C([O-])([O-])=O.[Na+].[Na+].CS(=O)C.O.C(C)#N.C1CCOC1 | Acylation | OtherReaction | 7f0731bb44e05053b427ee27fe964c9510939e60d570adf68d7728bd0b6ad4de | c77dcb628c46f34db12abe282042119a29544ea9236aafae076c5fc9c8355903 | O=C1N(c2ccc3ccc(S(=O)(=O)Nc4ccccc4)cc3c2)CCN1c1ccc2ccc(S(=O)(=O)Nc3ccccc3)cc2c1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[c:3]:[c:4](-[NH;D2;+0:5]-[C:6]-[C:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[N;H0;D3;+0:5](-[c:4](:[c:3]):[c:12])-[C:6]-[C:7]-[N;H0;D3;+0:8]-1-[c:9](:[c:10]):[c:11] | null | [] | null | null | 15 | MINUTE | To 8 mg (0.011 mmol) of compound 121 in 2 mL of saturated sodium carbonate and 2 mL of water was added 3 mg (0.010 mmol) of triphosgene dissolved in 0.5 mL of THF, dropwise. The addition was made over a period of 15 min. The reaction was judged incomplete by HPLC, so another 4.5 mg (0.015 mmol) of triphosgene in 0.5 mL... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Secondary amine.Secondary amine | Urea | null | C1C[NH]C[NH]1 | c1ccccc1.c1ccc2ccccc2c1.C1C[NH]C[NH]1.c1ccc2ccccc2c1.c1ccccc1 | HCl | O.C([O-])([O-])=O.[Na+].[Na+].CS(=O)C.O.C(C)#N.C1CCOC1 | null | 0.25 | O=C(O)c1cc(NS(=O)(=O)c2ccc3ccc(NCCNc4ccc5ccc(S(=O)(=O)Nc6ccc(O)c(C(=O)O)c6)cc5c4)cc3c2)ccc1O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>O.C([O-])([O-])=O.[Na+].[Na+].CS(=O)C.O.C(C)#N.C1CCOC1>O=C(O)c1cc(NS(=O)(=O)c2ccc3ccc(N4CCN(c5ccc6ccc(S(=O)(=O)Nc7ccc(O)c(C(=O)O)c7)cc6c5)C4=O)cc3c2)ccc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f09e7bbc3f314d7ea743e1a38425437f | O=[N+]([O-])c1ccc2ccc([N+](=O)[O-])cc2c1>>Nc1ccc2ccc(N)cc2c1 | [OH-].[Na+].[N+](=O)([O-])C1=CC2=CC(=CC=C2C=C1)[N+](=O)[O-].Cl.[Sn](Cl)Cl>>C1=C(C=CC2=CC=C(C=C12)N)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][c:8]([N+:9](=O)[O-])[cH:10][c:11]2[cH:12]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][c:8]([NH2:9])[cH:10][c:11]2[cH:12]1 | O=[N+]([O-])c1ccc2ccc([N+](=O)[O-])cc2c1 | Nc1ccc2ccc(N)cc2c1 | null | null | C(C)O | Reduction | OtherReaction | 6748a51a25102225412593c5a930e43f5a8904a80803177de025a6f83c59d65e | a303b0dfb15cc6bade463acf71681cf3ba7580b599dfa4d28d8caac83d08cd17 | c1ccc2ccccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4].O=[N+;H0;D3:5](-[O-])-[c:6](:[c:7]):[c:8]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | To 1.39 g (6.37 mmol) of 2,7-dinitronaphthalene (124) was added 25 mL of concentrated HCl and 15 mL of ethanol. Then, 9.6 g (50.9 mmol) of tin (II) chloride was added and the reaction was heated at 78 C for 24 hours. The reaction was made basic with NaOH and extracted with ethyl acetate. The ethyl acetate layer was dri... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group | Primary amine.Primary amine | null | null | c1ccc2ccccc2c1 | Other | C(C)O | null | null | O=[N+]([O-])c1ccc2ccc([N+](=O)[O-])cc2c1>C(C)O>Nc1ccc2ccc(N)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-77a1cfdf137a4ffeacaf6115c448d4a7 | CC(=O)OC(C)=O.Nc1ccc2ccc(S(=O)(=O)O)cc2c1>>CC(=O)Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1 | NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)O.NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)O.N1=CC=CC=C1.C(C)(=O)OC(C)=O.C[O-].[Na+]>>[Na+].C(C)(=O)NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)[O-] | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][c:11]([S:12](=[O:13])(=[O:14])[OH:15])[cH:16][c:17]2[cH:18]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][c:11]([S:12](=[O:13])(=[O:14])[O-:15])[cH:16][c:17]2[cH:18]1 | CC(=O)OC(C)=O.Nc1ccc2ccc(S(=O)(=O)O)cc2c1 | CC(=O)Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1 | null | null | CO | Acylation | OtherReaction | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccc2ccccc2c1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7].[O;D1;H0:8]=[#16:9](=[O;D1;H0:10])(-[OH;D1;+0:11])-[c:12]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7].[O-;H0;D1:11]-[#16:9](=[O;D1;H0:8])(=[O;D1;H0:10])-[c:12] | null | [] | null | null | 24 | HOUR | To 3.75 g (16.8 mmol) of 7-amino-naphthalene-2-sulfonic acid (compound 1) was added 20 mL each of pyridine and acetic anhydride. The reaction was allowed to stir at ambient temperature for 24 hours. The black reaction was cooled in an ice bath and then 45 mL of methanol was added slowly. After 1 hour, a solution of sod... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccc2ccccc2c1 | HO- | CO | null | 24 | CC(=O)OC(C)=O.Nc1ccc2ccc(S(=O)(=O)O)cc2c1>CO>CC(=O)Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-db77f95e579e42a3a79ed51eedf09b95 | CC(=O)Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1.O=P(Cl)(Cl)Cl>>CC(=O)Nc1ccc2ccc(S(=O)(=O)Cl)cc2c1 | [Na+].C(C)(=O)NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)[O-].P(=O)(Cl)(Cl)Cl>>ClS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NC(C)=O | [O-][S:12]([c:11]1[cH:10][cH:9][c:8]2[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:18][c:17]2[cH:16]1)(=[O:13])=[O:14].O=P(Cl)(Cl)[Cl:15]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][c:11]([S:12](=[O:13])(=[O:14])[Cl:15])[cH:16][c:17]2[cH:18]1 | CC(=O)Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1.O=P(Cl)(Cl)Cl | CC(=O)Nc1ccc2ccc(S(=O)(=O)Cl)cc2c1 | null | null | CC(=O)N(C)C | Functional Group Interconversion | OtherReaction | 1d60417dbcce8291d459a7fb34824cf29ea6f69a30ac46aeb585ac8e7b69013e | 4a93b4a9749514113cd3dffa44b64f21b1f88d26b8739299bcad711fe7a13a1b | c1ccc2ccccc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].[O-]-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7]>>[Cl;H0;D1;+0:1]-[S;H0;D4;+0:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 5 | HOUR | To 3.6 g (12.5 mmol) of compound 130 was added 100 mL of phosphorous oxychloride. Then, 4 mL of dimethylacetamide was added dropwise. The reaction was allowed to stir at ambient temperature for 5 hours and then was poured onto 2 L of ice. After the ice had melted, the solid precipitate was collected by vacuum filtratio... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonic acid | Sulfonyl halide | null | null | c1ccc2ccccc2c1 | Other | CC(=O)N(C)C | null | 5 | CC(=O)Nc1ccc2ccc(S(=O)(=O)[O-])cc2c1.O=P(Cl)(Cl)Cl>CC(=O)N(C)C>CC(=O)Nc1ccc2ccc(S(=O)(=O)Cl)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-48b67bb86430442891c6a781a03a2169 | CC(=O)Nc1ccc2ccc(S(=O)(=O)Cl)cc2c1.Nc1ccc(Cl)c(C(=O)O)c1>>CC(=O)Nc1ccc2ccc(S(=O)(=O)Nc3ccc(Cl)c(C(=O)O)c3)cc2c1 | NC=1C=CC(=C(C(=O)O)C1)Cl.ClS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NC(C)=O>>C(C)(=O)NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)NC=1C=CC(=C(C(=O)O)C1)Cl | Cl[S:12]([c:11]1[cH:10][cH:9][c:8]2[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:28][c:27]2[cH:26]1)(=[O:13])=[O:14].[NH2:15][c:16]1[cH:17][cH:18][c:19]([Cl:20])[c:21]([C:22](=[O:23])[OH:24])[cH:25]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][c:11]([S:12](=[O:13])(=[O:14])[NH:15][c:16]3[cH:17][... | CC(=O)Nc1ccc2ccc(S(=O)(=O)Cl)cc2c1.Nc1ccc(Cl)c(C(=O)O)c1 | CC(=O)Nc1ccc2ccc(S(=O)(=O)Nc3ccc(Cl)c(C(=O)O)c3)cc2c1 | null | null | N1=CC=CC=C1.C1CCOC1 | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=S(=O)(Nc1ccccc1)c1ccc2ccccc2c1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | null | [] | 5 | CELSIUS | 30 | MINUTE | To 15 g (0.087 mol) of 5-amino-2-chlorobenzoic acid was dissolved in 450 mL of THF and 15 mL of pyridine. The solution was cooled to 5° C. in an ice-water bath. Then, a solution of 20.8 g (0.074 mol) of compound 131 dissolved in 200 mL of THF was added over a 10 min period. The reaction was kept at 5° C. for 30 min, an... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2ccccc2c1.c1ccccc1 | HCl | N1=CC=CC=C1.C1CCOC1 | 5 | 0.5 | CC(=O)Nc1ccc2ccc(S(=O)(=O)Cl)cc2c1.Nc1ccc(Cl)c(C(=O)O)c1>N1=CC=CC=C1.C1CCOC1>CC(=O)Nc1ccc2ccc(S(=O)(=O)Nc3ccc(Cl)c(C(=O)O)c3)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7d3bb904dce746a8b16c8f0c5634b4a1 | CC(=O)Nc1ccc2ccc(S(=O)(=O)Nc3ccc(Cl)c(C(=O)O)c3)cc2c1>>Nc1ccc2ccc(S(=O)(=O)Nc3ccc(Cl)c(C(=O)O)c3)cc2c1 | C(C)(=O)NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)NC=1C=CC(=C(C(=O)O)C1)Cl.Cl>>NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)NC=1C=CC(=C(C(=O)O)C1)Cl | CC(=O)[NH:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][c:8]([S:9](=[O:10])(=[O:11])[NH:12][c:13]3[cH:14][cH:15][c:16]([Cl:17])[c:18]([C:19](=[O:20])[OH:21])[cH:22]3)[cH:23][c:24]2[cH:25]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][c:8]([S:9](=[O:10])(=[O:11])[NH:12][c:13]3[cH:14][cH:15][c:16]([Cl:17])[c:18]([C:19](=[O:20])... | CC(=O)Nc1ccc2ccc(S(=O)(=O)Nc3ccc(Cl)c(C(=O)O)c3)cc2c1 | Nc1ccc2ccc(S(=O)(=O)Nc3ccc(Cl)c(C(=O)O)c3)cc2c1 | null | null | [OH-].[Na+] | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | O=S(=O)(Nc1ccccc1)c1ccc2ccccc2c1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 93.7 | [{"value": 93.7, "product": "NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)NC=1C=CC(=C(C(=O)O)C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To 13.5 g (0.032 mol) of compound 132 was added 100 mL of 5N NaOH. This solution was heated at 50° C. for 8 hours. Then, the reaction was acidified-with 86 mL of 6N HCl and extracted with ethyl acetate. The ethyl acetate was washed with 1N HCl, water, and brine. The organic layer was dried (MgSO4), filtered, and the vo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccc2ccccc2c1.c1ccccc1 | HO- | [OH-].[Na+] | 50 | null | CC(=O)Nc1ccc2ccc(S(=O)(=O)Nc3ccc(Cl)c(C(=O)O)c3)cc2c1>[OH-].[Na+]>Nc1ccc2ccc(S(=O)(=O)Nc3ccc(Cl)c(C(=O)O)c3)cc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9d217d3fb93145c49068748249c315f8 | CO.Nc1ccc2ccc(S(=O)(=O)Nc3ccc(Cl)c(C(=O)O)c3)cc2c1>>COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N)cc3c2)ccc1Cl | NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)NC=1C=CC(=C(C(=O)O)C1)Cl.CO.Cl>>NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)NC=1C=CC(=C(C(=O)OC)C1)Cl | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][c:18]([NH2:19])[cH:20][c:21]3[cH:22]2)[cH:23][cH:24][c:25]1[Cl:26]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][c:18]([NH2:19])[cH:... | CO.Nc1ccc2ccc(S(=O)(=O)Nc3ccc(Cl)c(C(=O)O)c3)cc2c1 | COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N)cc3c2)ccc1Cl | null | null | O1CCOCC1 | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | O=S(=O)(Nc1ccccc1)c1ccc2ccccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 18 | HOUR | To 10.1 g (0.027 mol) of compound 133 dissolved in 250 mL of methanol was added 50 mL of 4 N HCl in dioxane. This solution was allowed to stir at ambient temperature for 18 hours. The reaction was incomplete, so it was heated at reflux for an additional 5 hours. Then, the volatiles were removed by rotary evaporation an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1.c1ccc2ccccc2c1 | HO- | O1CCOCC1 | null | 18 | CO.Nc1ccc2ccc(S(=O)(=O)Nc3ccc(Cl)c(C(=O)O)c3)cc2c1>O1CCOCC1>COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N)cc3c2)ccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c2b8f19994364a4d98d0897d016a3821 | COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N)cc3c2)ccc1Cl.S=C(n1ccnc1)n1ccnc1>>COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N=C=S)cc3c2)ccc1Cl | NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)NC=1C=CC(=C(C(=O)OC)C1)Cl.C(=S)(N1C=NC=C1)N1C=NC=C1.C1CCOC1>>ClC1=C(C(=O)OC)C=C(C=C1)NS(=O)(=O)C1=CC2=CC(=CC=C2C=C1)N=C=S | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][c:18]([NH2:19])[cH:22][c:23]3[cH:24]2)[cH:25][cH:26][c:27]1[Cl:28].c1cn([C:20](n2ccnc2)=[S:21])cn1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][c:15]3[cH:1... | COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N)cc3c2)ccc1Cl.S=C(n1ccnc1)n1ccnc1 | COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N=C=S)cc3c2)ccc1Cl | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | be7cda7c305cb7fe0f9c01bbc607472f3b10db5b9ac4c3f6176bd6d49196c1b0 | b9d004d515d4691c0e9944172fdecaa5dd531c6cfbffee450da8866f92f0f7d4 | O=S(=O)(Nc1ccccc1)c1ccc2ccccc2c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:5]=[C;H0;D3;+0:6](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[S;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | 95.8 | [{"value": 95.8, "product": "ClC1=C(C(=O)OC)C=C(C=C1)NS(=O)(=O)C1=CC2=CC(=CC=C2C=C1)N=C=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To 4.5 g (11.5 mmol) of compound 134 and 9.01 g (50.6 mmol) of 1,1′-thiocarbonyldiimidazole was added 50 mL of THF. The solution was allowed to stir at ambient temperature for 1.5 hours. Then, the reaction was poured into 300 mL of ethyl acetate and extracted with 1N HCl, water, and brine. The organic layer was dried (... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Thiocarbonyl | Isothiocyanate | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1.c1ccc2ccccc2c1 | Other | C(C)(=O)OCC | null | 1.5 | COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N)cc3c2)ccc1Cl.S=C(n1ccnc1)n1ccnc1>C(C)(=O)OCC>COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N=C=S)cc3c2)ccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9254a5d95bdd437794466ad3d5cabb83 | COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N=C=S)cc3c2)ccc1Cl.Nc1ccc2c(O)cc(S(=O)(=O)Nc3cccc(S(=O)(=O)[O-])c3)cc2c1>>COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(NC(=S)Nc4ccc5c(O)cc(S(=O)(=O)Nc6cccc(S(=O)(=O)O)c6)cc5c4)cc3c2)ccc1Cl | ClC1=C(C(=O)OC)C=C(C=C1)NS(=O)(=O)C1=CC2=CC(=CC=C2C=C1)N=C=S.[Na+].NC1=CC=C2C(=CC(=CC2=C1)S(=O)(=O)NC=1C=C(C=CC1)S(=O)(=O)[O-])O>>ClC1=C(C=C(C=C1)NS(=O)(=O)C1=CC=C2C=CC(=CC2=C1)NC(=S)NC1=CC=C2C(=CC(=CC2=C1)S(=O)(=O)NC=1C=C(C=CC1)S(=O)(=O)O)O)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][c:18]([N:19]=[C:20]=[S:21])[cH:48][c:49]3[cH:50]2)[cH:51][cH:52][c:53]1[Cl:54].[NH2:22][c:23]1[cH:24][cH:25][c:26]2[c:27]([OH:28])[cH:29][c:30]([S:31](=[O:32])(=[O:33])[NH:34][c:35]3[cH:36][cH:37][cH:38][c... | COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N=C=S)cc3c2)ccc1Cl.Nc1ccc2c(O)cc(S(=O)(=O)Nc3cccc(S(=O)(=O)[O-])c3)cc2c1 | COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(NC(=S)Nc4ccc5c(O)cc(S(=O)(=O)Nc6cccc(S(=O)(=O)O)c6)cc5c4)cc3c2)ccc1Cl | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | O=S(=O)(Nc1ccccc1)c1ccc2ccc(NC(=S)Nc3ccc4ccc(S(=O)(=O)Nc5ccccc5)cc4c3)cc2c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O-;H0;D1:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9].[S;D1;H0:10]=[C;H0;D2;+0:11]=[N;H0;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[O;D1;H0:7]=[#16:6](=[O;D1;H0:8])(-[OH;D1;+0:5])-[c:9].[S;D1;H0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15])-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 4 | DAY | To 170 mg (0.39 mmol) of compound 135 dissolved in 5 mL of DMF was added a solution of 100 mg (0.25 mmol) of compound 18 in 5 mL of DMF. The reaction was allowed to stir at ambient temperature. After 4 days, the DMF was removed by rotary evaporation and kept under high vacuum to remove traces of DMF. Then, the resultin... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | c1ccccc1.c1ccc2ccccc2c1.c1ccc2ccccc2c1.c1ccccc1 | null | CN(C)C=O | null | 96 | COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N=C=S)cc3c2)ccc1Cl.Nc1ccc2c(O)cc(S(=O)(=O)Nc3cccc(S(=O)(=O)[O-])c3)cc2c1>CN(C)C=O>COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(NC(=S)Nc4ccc5c(O)cc(S(=O)(=O)Nc6cccc(S(=O)(=O)O)c6)cc5c4)cc3c2)ccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-de621f935b8f431f98196f90fe51bfa6 | COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N)cc3c2)ccc1Cl.COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N=C=S)cc3c2)ccc1Cl>>COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(NC(=S)Nc4ccc5ccc(S(=O)(=O)Nc6ccc(Cl)c(C(=O)OC)c6)cc5c4)cc3c2)ccc1Cl | NC1=CC=C2C=CC(=CC2=C1)S(=O)(=O)NC=1C=CC(=C(C(=O)OC)C1)Cl.ClC1=C(C(=O)OC)C=C(C=C1)NS(=O)(=O)C1=CC2=CC(=CC=C2C=C1)N=C=S>>ClC1=C(C(=O)OC)C=C(C=C1)NS(=O)(=O)C1=CC2=CC(=CC=C2C=C1)NC(=S)NC1=CC2=CC(=CC=C2C=C1)S(=O)(=O)NC1=CC(=C(C=C1)Cl)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][c:15]3[cH:16][cH:17][c:18]([NH2:19])[cH:48][c:49]3[cH:50]2)[cH:51][cH:52][c:53]1[Cl:54].[C:20](=[S:21])=[N:22][c:23]1[cH:24][cH:25][c:26]2[cH:27][cH:28][c:29]([S:30](=[O:31])(=[O:32])[NH:33][c:34]3[cH:35][cH:36][c:37]([Cl:38])... | COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N)cc3c2)ccc1Cl.COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N=C=S)cc3c2)ccc1Cl | COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(NC(=S)Nc4ccc5ccc(S(=O)(=O)Nc6ccc(Cl)c(C(=O)OC)c6)cc5c4)cc3c2)ccc1Cl | null | null | ClCCl | Heteroatom Alkylation and Arylation | thiourea | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | O=S(=O)(Nc1ccccc1)c1ccc2ccc(NC(=S)Nc3ccc4ccc(S(=O)(=O)Nc5ccccc5)cc4c3)cc2c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[S;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 82.2 | [{"value": 82.2, "product": "ClC1=C(C(=O)OC)C=C(C=C1)NS(=O)(=O)C1=CC2=CC(=CC=C2C=C1)NC(=S)NC1=CC2=CC(=CC=C2C=C1)S(=O)(=O)NC1=CC(=C(C=C1)Cl)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | To 3.0 g (7.68 mmol) of compound 134 was added a solution of 4.0 g (9.24 mmol) of compound 135 in 200 mL of dichloromethane. The reaction was allowed to stir at ambient temperature for 48 hours. The fine, white solid was collected to give 5.2 g of compound 157.
Conditions: See reaction.notes.procedure_details.
Workup: ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | c1ccccc1.c1ccc2ccccc2c1.c1ccc2ccccc2c1.c1ccccc1 | null | ClCCl | null | 48 | COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N)cc3c2)ccc1Cl.COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(N=C=S)cc3c2)ccc1Cl>ClCCl>COC(=O)c1cc(NS(=O)(=O)c2ccc3ccc(NC(=S)Nc4ccc5ccc(S(=O)(=O)Nc6ccc(Cl)c(C(=O)OC)c6)cc5c4)cc3c2)ccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-07a7655d22c44b9194cd699db25c9830 | Nc1ccc(OCCO)c(N)c1.O=Cc1ccccc1>>Nc1cc(NCc2ccccc2)ccc1OCCO | NC1=C(OCCO)C=CC(=C1)N.C(C1=CC=CC=C1)=O.B.O1CCCC1>>NC1=C(OCCO)C=CC(=C1)NCC1=CC=CC=C1 | [NH2:1][c:2]1[cH:3][c:4]([NH2:5])[cH:13][cH:14][c:15]1[O:16][CH2:17][CH2:18][OH:19].O=[CH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[NH2:1][c:2]1[cH:3][c:4]([NH:5][CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[cH:13][cH:14][c:15]1[O:16][CH2:17][CH2:18][OH:19] | Nc1ccc(OCCO)c(N)c1.O=Cc1ccccc1 | Nc1cc(NCc2ccccc2)ccc1OCCO | null | null | O1CCCC1.CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CNc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | null | [] | null | null | 7 | HOUR | 2.66 g (10 mmol) of 2-(2,4-diaminophenoxy)ethanol and 1.06 g (10 mmol) of benzaldehyde were dissolved in methanol (dried over molecular sieve). After addition of 10 mg of molecular sieve, the reaction mixture was allowed to agitate 7 hours. Then, 20 mL of a solution of borane-tetrahydrofuran com-plex (1 M in tetrahydro... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | O1CCCC1.CO | null | 7 | Nc1ccc(OCCO)c(N)c1.O=Cc1ccccc1>O1CCCC1.CO>Nc1cc(NCc2ccccc2)ccc1OCCO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d4243873cd4a41a4b34b7ae55d858f59 | Ic1ccccc1.c1ccc(-c2ncc[nH]2)nc1>>c1ccc(-n2ccnc2-c2ccccn2)cc1 | N1=C(C=CC=C1)C=1NC=CN1.IC1=CC=CC=C1.C(=O)([O-])[O-].[Cs+].[Cs+]>>C1(=CC=CC=C1)N1C(=NC=C1)C1=NC=CC=C1 | I[c:4]1[cH:3][cH:2][cH:1][cH:17][cH:16]1.[nH:5]1[cH:6][cH:7][n:8][c:9]1-[c:10]1[cH:11][cH:12][cH:13][cH:14][n:15]1>>[cH:1]1[cH:2][cH:3][c:4](-[n:5]2[cH:6][cH:7][n:8][c:9]2-[c:10]2[cH:11][cH:12][cH:13][cH:14][n:15]2)[cH:16][cH:17]1 | Ic1ccccc1.c1ccc(-c2ncc[nH]2)nc1 | c1ccc(-n2ccnc2-c2ccccn2)cc1 | null | [Cu] | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 03854e27c36c357a72ea8df438000a0731263e0929d803025abb25baf2816b5b | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2-c2ccccn2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7;a:6]:[c:7]-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1>>[#7;a:6]:[c:7]-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[n;H0;D3;+0:12]:1-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | 2-(2-pyridyl)imidazole (6.91 g), iodobenzene (11.47 g), Cs2CO3 (25 g), and copper powder (15 g) were mixed in 60 mL anhydrous DMF in a 250 mL round bottom flask equipped with a magnetic stirrer and a reflux condesner. The mixture is degassed with N2 for 15 minutes at room temperature and then refluxed under N2 in an oi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1.c1c[nH]cn1 | c1ccccc1.c1ncc[nH]1 | c1ccccc1.c1ncc[nH]1.c1ccncc1 | HI | [Cu].CN(C)C=O | null | null | Ic1ccccc1.c1ccc(-c2ncc[nH]2)nc1>[Cu].CN(C)C=O>c1ccc(-n2ccnc2-c2ccccn2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-02215aa8ae9d45eb9264057804da3dfe | CCOC(=O)CN(CCN(CCN(CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O>>CCOC(=O)CN(CCN(CCN1CC(=O)OC(=O)C1)CC(=O)O)CC(=O)O | C(=O)(O)CN(CC(=O)O)CCN(CCN(CC(=O)O)CC(=O)OCC)CC(=O)O.N1=CC=CC=C1>>O=C1OC(CN(C1)CCN(CC(=O)O)CCN(CC(=O)O)CC(=O)OCC)=O | O[C:18](=[O:19])[CH2:20][N:13]([CH2:12][CH2:11][N:10]([CH2:9][CH2:8][N:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:25][C:26](=[O:27])[OH:28])[CH2:21][C:22](=[O:23])[OH:24])[CH2:14][C:15](=[O:16])[OH:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]([CH2:8][CH2:9][N:10]([CH2:11][CH2:12][N:13]1[CH2:14][C:15](=[O:16])... | CCOC(=O)CN(CCN(CCN(CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O | CCOC(=O)CN(CCN(CCN1CC(=O)OC(=O)C1)CC(=O)O)CC(=O)O | null | null | C(C)(=O)OC(C)=O | Miscellaneous | OtherReaction | 531356c2a2275fd45e5fe40cca6a0e44e1335d37c344fc2e6fa4338d12f7e5b0 | 22fb50577915472f1babb105381e408122dc09b3472eabb73e6e4daecfef90f6 | O=C1CNCC(=O)O1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[O;D1;H0:7]=[C:6]1-[C:5]-[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-1 | null | [] | null | null | 3 | DAY | A suspension of 21.1 g (50 mmol) of N3,N6-bis-(carboxymethyl)-N9-(ethoxy-carbonylmethyl)-3,6,9-triazaundecanedioic acid in 250 ml of acetic anhydride is allowed to stir for three days at room temperature after the addition of 42.2 ml of pyridine. Then, the precipitate is suctioned off, washed three times with 50 ml of ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | Anhydride | null | C1COCC[NH]1 | C1COCC[NH]1 | HO- | C(C)(=O)OC(C)=O | null | 72 | CCOC(=O)CN(CCN(CCN(CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O>C(C)(=O)OC(C)=O>CCOC(=O)CN(CCN(CCN1CC(=O)OC(=O)C1)CC(=O)O)CC(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ad13a89846244846b20e0bc80585411a | CCOC(=O)CN(CCN(CCN1CC(=O)OC(=O)C1)CC(=O)O)CC(=O)O.NCCCCCCCCCCC(=O)O>>O=C(O)CCCCCCCCCCNC(=O)CN(CCN(CCN(CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O | O=C1OC(CN(C1)CCN(CC(=O)O)CCN(CC(=O)O)CC(=O)OCC)=O.C(C)N(CC)CC.NCCCCCCCCCCC(=O)O>>C(=O)(O)CN(CC(=O)O)CCN(CCN(CC(=O)O)CC(NCCCCCCCCCCC(=O)O)=O)CC(=O)O | CC[O:28][C:15](=[O:16])[CH2:17][N:18]([CH2:19][CH2:20][N:21]([CH2:22][CH2:23][N:24]1[CH2:25][C:26](=[O:27])[O:32][C:30](=[O:31])[CH2:29]1)[CH2:33][C:34](=[O:35])[OH:36])[CH2:37][C:38](=[O:39])[OH:40].[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14]>>[O:1]=[C:2]([OH:3... | CCOC(=O)CN(CCN(CCN1CC(=O)OC(=O)C1)CC(=O)O)CC(=O)O.NCCCCCCCCCCC(=O)O | O=C(O)CCCCCCCCCCNC(=O)CN(CCN(CCN(CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O | null | null | CN(C=O)C | Protection | OtherReaction | 380041781ec6e021c96aea4edbd2b8eb6e47bf3d5a17e31bc58e8919fdfcd6b6 | f1df8e156b67a57efc2a412484a5cb2864f2dbf49f0d06e51b2a8082745c9eed | null | C-C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4]-[#7:5].[C:6]-[#7:7]1-[C:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-[C:12](=[O;D1;H0:13])-[C:14]-1.[C:15]-[C:16]-[NH2;D1;+0:17]>>[#7:5]-[C:4]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[NH;D2;+0:17]-[C:16]-[C:15].[C:6]-[#7:7](-[C:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[OH;D1;+0:1]... | null | [] | null | null | 8 | HOUR | 15.33 g (38 mmol) of N3-(2,6-dioxomorpholinoethyl)-N6-(ethoxy-carbonylmethyl)-3,6-diazaoctanedioic acid (Example 13a of EP 0331 616) is suspended in dimethylformamide (DMF) and mixed in an ice bath with 21.07 ml (152 mmol) of triethylamine and 7.65 g (38 mmol) of 11-aminoundecanoic acid. The temperature-is allowed to i... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Primary amine | Carboxylic acid.Carboxylic acid.Secondary amide | C1COCC[NH]1 | null | null | Other | CN(C=O)C | null | 8 | CCOC(=O)CN(CCN(CCN1CC(=O)OC(=O)C1)CC(=O)O)CC(=O)O.NCCCCCCCCCCC(=O)O>CN(C=O)C>O=C(O)CCCCCCCCCCNC(=O)CN(CCN(CCN(CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4e53680c6d4e485fa42a2e0d75347170 | CCCCCCC(N)CCCCCCCCCCC(=O)O.CCOC(=O)CN(CCN(CCN1CC(=O)OC(=O)C1)CC(=O)O)CC(=O)O>>CCCCCCC(C(=O)NCCCCCCCCCCCC(=O)O)N(CCN(CCN(CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O | Cl.O=C1OC(CN(C1)CCN(CC(=O)O)CCN(CC(=O)O)CC(=O)OCC)=O.C(C)N(CC)CC.NC(CCCCCCCCCCC(=O)O)CCCCCC>>C(=O)(O)CN(CC(=O)O)CCN(CCN(CC(=O)O)C(CCCCCC)C(NCCCCCCCCCCCC(=O)O)=O)CC(=O)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:11]([NH2:10])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:23])[OH:24].CC[O:35][C:33]([CH2:32][N:31]([CH2:30][CH2:29][N:28]([CH2:27][CH2:26][N:25]1[CH2:7][C:8](=[O:9])[O:47][C:45](=[O:46])[CH2:44]1)[CH2:40][C:41](=[O:42])[OH:43])... | CCCCCCC(N)CCCCCCCCCCC(=O)O.CCOC(=O)CN(CCN(CCN1CC(=O)OC(=O)C1)CC(=O)O)CC(=O)O | CCCCCCC(C(=O)NCCCCCCCCCCCC(=O)O)N(CCN(CCN(CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O | null | null | CN(C=O)C.[OH-].[Na+] | C-C Coupling | OtherReaction | c4b83999322515c2025d6fa8d6cd55523e7dc129860df00d93d56b7ae844453c | 67cc23faed448bed090055ee8538881132d17845d3c53822f057dc740ab781a9 | null | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].[C:5]-[#7:6]1-[C:7]-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:10]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[CH2;D2;+0:13]-1.[C:14]-[C:15]-[CH;D3;+0:16](-[NH2;D1;+0:17])-[CH2;D2;+0:18]-[C:19]-[C:20]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1].[C:14]-[C:15]-[CH2;D2;+0:16]-[NH;D2;+0:17]-[C;H0;D3;+0:11... | null | [] | null | null | 8 | HOUR | 15.33 g (38 mmol) of N3-(2,6-dioxomorpholinoethyl)-N6-(ethoxycarbonylmethyl)-3,6-diazaoctanedioic acid (Example 13a of EP 0 331 616) is suspended in 100 ml of dimethylformamide and mixed in an ice bath with 21.07 ml (152 mmol) of triethylamine and 11.36 g (38 mmol) of 12-aminooctadecanoic acid. After stirring overnight... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Primary amine | Carboxylic acid.Carboxylic acid.Secondary amide | C1COCC[NH]1 | null | null | Other | CN(C=O)C.[OH-].[Na+] | null | 8 | CCCCCCC(N)CCCCCCCCCCC(=O)O.CCOC(=O)CN(CCN(CCN1CC(=O)OC(=O)C1)CC(=O)O)CC(=O)O>CN(C=O)C.[OH-].[Na+]>CCCCCCC(C(=O)NCCCCCCCCCCCC(=O)O)N(CCN(CCN(CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-10e17dc4545e4605acbd5f1b6026a6d2 | CCOC(=O)CCCCCCCCCCN.O.O=C(O)CN(CCN1CC(=O)OC(=O)C1)CCN1CC(=O)OC(=O)C1>>CCOC(=O)CCCCCCCCCCNC(=O)CN(CCN(CCN(CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O | C(C)OC(CCCCCCCCCCN)=O.O.O=C1OC(CN(C1)CCN(CCN1CC(OC(C1)=O)=O)CC(=O)O)=O.C(C)N(CC)CC>>C(=O)(O)CN(CC(=O)O)CCN(CCN(CC(=O)O)CC(NCCCCCCCCCCC(=O)OCC)=O)CC(=O)O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16].[OH2:30].[C:17]1(=[O:18])[CH2:19][N:20]([CH2:21][CH2:22][N:26]([CH2:25][CH2:24][N:23]2[CH2:27][C:28](=[O:29])[O:38][C:36](=[O:37])[CH2:35]2)[CH2:31][C:32](=[O:33])[OH:34])[CH2:39][C:40](=[O:41])[O:42]1>>... | CCOC(=O)CCCCCCCCCCN.O.O=C(O)CN(CCN1CC(=O)OC(=O)C1)CCN1CC(=O)OC(=O)C1 | CCOC(=O)CCCCCCCCCCNC(=O)CN(CCN(CCN(CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O | null | null | CN(C=O)C | Protection | OtherReaction | 6bc1b01e4b2a6ffd6e7b8a96449c701acb4c4580c36842068019c63484004e32 | d7a98c1bd84add8ab431ff626f1143e7bbdf5491ba5aba32fcd183898e611844 | null | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-[C:6]-[#7:7](-[C:8]-[CH2;D2;+0:9]-[N;H0;D3;+0:10](-[C:11]-[C:12]-[N;H0;D3;+0:13]2-[C:14]-[C:15](=[O;D1;H0:16])-[O;H0;D2;+0:17]-[C;H0;D3;+0:18](=[O;D1;H0:19])-[CH2;D2;+0:20]-2)-[C:21]-[C:22](=[O;D1;H0:23])-[O;D1;H1:24])-[C:25]-[C:26](=[O;D1;H0:27])-[O;H0;D2;+0:28]-1.... | null | [] | 0 | CELSIUS | 8 | HOUR | 17.85 g (50 mmol) of 1.5-bis(2,6-dioxomorpholino)-3-carboxymethyl-3-azapentane is stirred in 200 ml of dimethylformamide and mixed with 9 ml (50 mmol) of water. The solution is heated for 3 hours to 70° C., cooled off to 0° C. and 36.07 ml (260 mmol) of triethylamine and 10.8 g. (50 mmol) of 11-aminoundecanoic acid eth... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Anhydride.Primary amine.Tertiary amine.Tertiary amine | Carboxylic acid.Carboxylic acid.Carboxylic acid.Secondary amide.Tertiary amine.Tertiary amine | C1COCC[NH]1.C1COCC[NH]1 | null | null | null | CN(C=O)C | 0 | 8 | CCOC(=O)CCCCCCCCCCN.O.O=C(O)CN(CCN1CC(=O)OC(=O)C1)CCN1CC(=O)OC(=O)C1>CN(C=O)C>CCOC(=O)CCCCCCCCCCNC(=O)CN(CCN(CCN(CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6411025ed138462dab56e0528ebb048d | CC(C)=O.CCn1c2ccccc2c2cc(C=NNc3ccccc3)ccc21>>CCn1c2ccccc2c2cc(C=NN(CC3CO3)c3ccccc3)ccc21 | CC(=O)C.C1(=CC=CC=C1)NN=CC=1C=CC=2N(C3=CC=CC=C3C2C1)CC.[OH-].[K+].C([O-])([O-])=O.[K+].[K+]>>O1C(CN(N=CC=2C=CC=3N(C4=CC=CC=C4C3C2)CC)C2=CC=CC=C2)C1 | [CH3:16][C:17]([CH3:18])=[O:19].[CH3:1][CH2:2][n:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]2[cH:11][c:12]([CH:13]=[N:14][NH:15][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[cH:26][cH:27][c:28]12>>[CH3:1][CH2:2][n:3]1[c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]2[cH:11][c:12]([CH:13]=[N:14][N:15]([CH2:16][CH:17]3[CH2:18]... | CC(C)=O.CCn1c2ccccc2c2cc(C=NNc3ccccc3)ccc21 | CCn1c2ccccc2c2cc(C=NN(CC3CO3)c3ccccc3)ccc21 | null | null | CCCCCC.CCOCC.C(Cl)C1CO1 | Heteroatom Alkylation and Arylation | OtherReaction | fab722ef38a601fd1739cd08a99e5ec076c91cff7a01183180f30d68b8d21695 | c381c7be960abc6402148b22148f7b9195e144b71496bf572eed664bae8a3675 | C(=NN(CC1CO1)c1ccccc1)c1ccc2[nH]c3ccccc3c2c1 | [CH3;D1;+0:1]-[C;H0;D3;+0:2](-[CH3;D1;+0:3])=[O;H0;D1;+0:4].[c:5]-[C:6]=[#7:7]-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[c:5]-[C:6]=[#7:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[CH;D3;+0:2]1-[CH2;D2;+0:3]-[O;H0;D2;+0:4]-1)-[c:9](:[c:10]):[c:11] | 81.2 | [{"value": 81.2, "product": "O1C(CN(N=CC=2C=CC=3N(C4=CC=CC=C4C3C2)CC)C2=CC=CC=C2)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 9-ethyl-3-carbazolecarboxaldehyde phenylhydrazone (3.1 g, 0.01 mol), 85% powdered potassium hydroxide (2.0g, 0.03 mol) and anhydrous potassium carbonate (˜5 g) in 25 ml of epichlorohydrin was stirred vigorously at 55–60° C. for 1.5–2 h. The course of the reaction was monitored using thin layer chromatograp... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ketone | Hydrazone.Ether | null | C1CO1 | c1ccc2[nH]c3ccccc3c2c1.C1CO1.c1ccccc1 | null | CCCCCC.CCOCC.C(Cl)C1CO1 | null | null | CC(C)=O.CCn1c2ccccc2c2cc(C=NNc3ccccc3)ccc21>CCCCCC.CCOCC.C(Cl)C1CO1>CCn1c2ccccc2c2cc(C=NN(CC3CO3)c3ccccc3)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-069148c0b05f4b968626e4d378ff94fa | CCN(CC)c1ccc(C=NNc2ccccc2)cc1.CCn1c2ccccc2c2cc(C=NN(CC3CO3)c3ccccc3)ccc21>>CCN(CC)c1ccc(C=NN(CC2CO2)c2ccccc2)cc1 | C=O.C=O.O1C(CN(N=CC=2C=CC=3N(C4=CC=CC=C4C3C2)CC)C2=CC=CC=C2)C1.C1(=CC=CC=C1)NN=CC=1C=CC=2N(C3=CC=CC=C3C2C1)CC.C1(=CC=CC=C1)NN=CC1=CC=C(C=C1)N(CC)CC>>O1C(CN(N=CC2=CC=C(C=C2)N(CC)CC)C2=CC=CC=C2)C1 | c1ccc(N[N:11]=[CH:10][c:9]2[cH:8][cH:7][c:6]([N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:24][cH:23]2)cc1.CCn1c2ccccc2c2cc(C=N[N:12]([CH2:13][CH:14]3[CH2:15][O:16]3)[c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)ccc21>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[c:6]1[cH:7][cH:8][c:9]([CH:10]=[N:11][N:12]([CH2:13][CH:14]2[CH2:15][O:16... | CCN(CC)c1ccc(C=NNc2ccccc2)cc1.CCn1c2ccccc2c2cc(C=NN(CC3CO3)c3ccccc3)ccc21 | CCN(CC)c1ccc(C=NN(CC2CO2)c2ccccc2)cc1 | null | null | null | Miscellaneous | OtherReaction | 6153061b4e3a083876321a90bbb0deb4d9147b088afb8482e9dc329013fe267e | 3e3dfc80a83d48f6316e36c52138c943a5ea31e33faf54e487b20834d7c2611f | C(=NN(CC1CO1)c1ccccc1)c1ccccc1 | C-C-n1:c2:c:c:c:c:c:2:c2:c:c(-C=N-[N;H0;D3;+0:1](-[C:2]-[C:3]-[#8:4])-[c:5](:[c:6]):[c:7]):c:c:c:2:1.[c:8]-[C:9]=[N;H0;D2;+0:10]-N-c1:c:c:c:c:c:1>>[#8:4]-[C:3]-[C:2]-[N;H0;D3;+0:1](-[N;H0;D2;+0:10]=[C:9]-[c:8])-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | 4-(Diethylamino)benzaldehyde N-2,3-epoxypropyl-N-phenylhydrazone was prepared according to the preparation procedure above for 9-ethyl-3-carbazolecarboxaldehyde N-2,3-epoxypropyl-N-phenylhydrazone except that 9-ethyl-3-carbazolecarboxaldehyde phenylhydrazone was replaced by 4-(diethylamino)benzaldehyde phenylhydrazone ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Hydrazone | Hydrazone | c1ccccc1.c1ccc2c(c1)[nH]c1ccccc12 | null | c1ccccc1.C1CO1.c1ccccc1 | Other | null | null | null | CCN(CC)c1ccc(C=NNc2ccccc2)cc1.CCn1c2ccccc2c2cc(C=NN(CC3CO3)c3ccccc3)ccc21>>CCN(CC)c1ccc(C=NN(CC2CO2)c2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3c0d343101884f729a2fce032cbee5eb | CC(C)N(PN(C(C)C)C(C)C)C(C)C.CC(C)NC(C)C.ClP(Cl)Cl>>CC(C)N(C(C)C)P(Cl)N(C(C)C)C(C)C | C(C)O.P(Cl)(Cl)Cl.C(C)(C)NC(C)C.C(C)(C)N(C(C)C)PN(C(C)C)C(C)C>>C(C)(C)N(C(C)C)P(Cl)N(C(C)C)C(C)C | CC(C)N(P[N:10]([CH:11]([CH3:12])[CH3:13])[CH:14]([CH3:15])[CH3:16])C(C)C.[CH3:1][CH:2]([CH3:3])[NH:4][CH:5]([CH3:6])[CH3:7].Cl[P:8](Cl)[Cl:9]>>[CH3:1][CH:2]([CH3:3])[N:4]([CH:5]([CH3:6])[CH3:7])[P:8]([Cl:9])[N:10]([CH:11]([CH3:12])[CH3:13])[CH:14]([CH3:15])[CH3:16] | CC(C)N(PN(C(C)C)C(C)C)C(C)C.CC(C)NC(C)C.ClP(Cl)Cl | CC(C)N(C(C)C)P(Cl)N(C(C)C)C(C)C | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | eddffc1f18f661ae266fa22d5dc859f89fee229f95a5be5dd8c7a1850d7eeef4 | 7023d3ed6b14188f646fa90fe3304f94ed4f0a41636b000bac9906170704b7ef | null | C-C(-C)-N(-P-[N;H0;D3;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-C(-C)-C.Cl-[P;H0;D3;+0:8](-Cl)-[Cl;D1;H0:9].[C;D1;H3:10]-[C:11](-[C;D1;H3:12])-[NH;D2;+0:13]-[C:14](-[C;D1;H3:15])-[C;D1;H3:16]>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])-[N;H0;D3;+0:1](-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[P;H0;D3;+0:8](... | null | [] | null | null | null | null | Bis(diisopropylamino)chlorophosphine was synthesized by reacting phosphorous trichloride and diisopropylamine in toluene. Fifty ml of the resulting bis(diisopropylamino)phosphine was placed in a 250 ml flask and 3.01 ml of ethanol added slowly over a two minute period and the reaction allowed to proceed for several day... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Tertiary amine.Tertiary amine | Tertiary amine.Tertiary amine | null | null | null | HCl | C1(=CC=CC=C1)C | null | null | CC(C)N(PN(C(C)C)C(C)C)C(C)C.CC(C)NC(C)C.ClP(Cl)Cl>C1(=CC=CC=C1)C>CC(C)N(C(C)C)P(Cl)N(C(C)C)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ae3fde27d5384a0abeb45a1cc4589100 | [Na+]>>[Na+] | [OH-].[Na+].C(C(CO)(CO)N)O.Cl>>C(C(CO)(CO)N)O.[OH-].[Na+] | [Na+:9]>>[Na+:9] | [Na+] | [Na+] | null | null | C(C(CO)(CO)N)O.C(CN(CC(=O)O)CC(=O)O)N(CC(=O)O)CC(=O)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | 70 | CELSIUS | null | null | To determine if heating the damaged DNA in the presence of salt can improve the amplification of this substrate, damaged DNA (25 ngs) was heated to 70° C. in the presence of a salt (Tris-EDTA (10 mM Tris pH 8.0 and 1 mM EDTA)) for 3 minutes, 25 ngs of native damaged sample was added back, and then the sample was cooled... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C(CO)(CO)N)O.C(CN(CC(=O)O)CC(=O)O)N(CC(=O)O)CC(=O)O | 70 | null | [Na+]>C(C(CO)(CO)N)O.C(CN(CC(=O)O)CC(=O)O)N(CC(=O)O)CC(=O)O>[Na+] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d2cd221f66824146ab105082b7fe3cf0 | CC(C)(C)OC(=O)NCCNC(=O)CBr.O=C(O)C(F)(F)F>>NCCNC(=O)CBr.O=C([O-])C(F)(F)F | BrCC(=O)NCCNC(=O)OC(C)(C)C.C(=O)(C(F)(F)F)O>>BrCC(=O)NCCN.FC(C(=O)[O-])(F)F | CC(C)(C)OC(=O)[NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[CH2:7][Br:8].[O:9]=[C:10]([OH:11])[C:12]([F:13])([F:14])[F:15]>>[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[CH2:7][Br:8].[O:9]=[C:10]([O-:11])[C:12]([F:13])([F:14])[F:15] | CC(C)(C)OC(=O)NCCNC(=O)CBr.O=C(O)C(F)(F)F | NCCNC(=O)CBr.O=C([O-])C(F)(F)F | null | null | ClCCl | Miscellaneous | OtherReaction | 200e7d0959435927bf3c32fc3f5547fea1fb2f71ddf167eb875ef78ef2491016 | 796edf5e07ba922d73012dd142556048cdd6456bcf9a2eb329b31c354361ae94 | null | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].[F;D1;H0:4]-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[C:8](=[O;D1;H0:9])-[OH;D1;+0:10]>>[C:3]-[C:2]-[NH2;D1;+0:1].[F;D1;H0:4]-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[C:8](-[O-;H0;D1:10])=[O;D1;H0:9] | null | [] | null | null | 30 | MINUTE | N-bromoacetyl-N′-BOC-ethylenediamine (2 is dissolved in 50% TFA in dichloromethane (5 ml of the solution per mmol of 3) at 20° C. The deprotection is allowed to proceed for 30 min, then the reaction mixture is concentrated on a rotary evaporator and solidifies upon addition of dry ethyl ether. The solid material is fil... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Boc | Primary amine | null | null | null | HO- | ClCCl | null | 0.5 | CC(C)(C)OC(=O)NCCNC(=O)CBr.O=C(O)C(F)(F)F>ClCCl>NCCNC(=O)CBr.O=C([O-])C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8b1bf344afac4e4d9cf9c7827cded9e5 | COP(=O)(OC)OC.Nc1nc2c(ncn2[C@@H]2O[C@H](CO)C[C@H]2O)c(=O)[nH]1>>Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)O)C[C@H]2O)c(=O)[nH]1 | [C@@H]1([C@H](O)C[C@@H](CO)O1)N1C=NC=2C(=O)NC(N)=NC12.[C@@H]1([C@H](O)C[C@@H](CO)O1)N1C=NC=2C(=O)NC(N)=NC12.COP(=O)(OC)OC.P(=O)(Cl)(Cl)Cl>>P(=O)(O)(O)OC[C@@H]1C[C@H]([C@@H](O1)N1C=NC=2C(=O)NC(N)=NC12)O | CO[P:14](=[O:15])([O:16]C)[O:17]C.[NH2:1][c:2]1[n:3][c:4]2[c:5]([n:6][cH:7][n:8]2[C@@H:9]2[O:10][C@H:11]([CH2:12][OH:13])[CH2:18][C@H:19]2[OH:20])[c:21](=[O:22])[nH:23]1>>[NH2:1][c:2]1[n:3][c:4]2[c:5]([n:6][cH:7][n:8]2[C@@H:9]2[O:10][C@H:11]([CH2:12][O:13][P:14](=[O:15])([OH:16])[OH:17])[CH2:18][C@H:19]2[OH:20])[c:21](... | COP(=O)(OC)OC.Nc1nc2c(ncn2[C@@H]2O[C@H](CO)C[C@H]2O)c(=O)[nH]1 | Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)O)C[C@H]2O)c(=O)[nH]1 | null | null | null | Miscellaneous | OtherReaction | b33b5b1c73040794426b58710e9df43eb6afb05a97193d1888f3f09bbd78a740 | 4849e38d2a94a9c5b21fea707c1e620c71a7333634a90a3629cdbc24fcbff129 | O=c1[nH]cnc2c1ncn2[C@H]1CCCO1 | C-O-[P;H0;D4;+0:1](=[O;D1;H0:2])(-[O;H0;D2;+0:3]-C)-[O;H0;D2;+0:4]-C.[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[P;H0;D4;+0:1](=[O;D1;H0:2])(-[OH;D1;+0:3])-[OH;D1;+0:4] | null | [] | null | null | null | null | 3′-Deoxyguanosine (Compound 1, commercial product from Sigma, 50 mg, 0.19 mmol) was stirred overnight with trimethylphosphate (2 mL) and phosphorus oxychloride (53 μL, 0.57 mmol) at 6° C. The reaction was quenched by adding 20 mL of water and neutralizing with 1 M NaHCO3. DEAE-Sephadex chromatography using a linear gra... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Phosphate ester | null | null | c1ncc2[nH]cnc2n1.C1CCOC1 | HO- | null | null | null | COP(=O)(OC)OC.Nc1nc2c(ncn2[C@@H]2O[C@H](CO)C[C@H]2O)c(=O)[nH]1>>Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)O)C[C@H]2O)c(=O)[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0b53857d38af4d8296b902528530f856 | CI.Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)C[C@H]2O)c(=O)[nH]1>>CN1CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)C[C@H]2O)c2nc(N)[nH]c(=O)c21 | P(O)(=O)(OP(=O)(O)O)OC[C@@H]1C[C@H]([C@@H](O1)N1C=NC=2C(=O)NC(N)=NC12)O.CS(=O)C.CN(C)C=O.CI>>P(O)(=O)(OP(=O)(O)O)OC[C@@H]1C[C@H]([C@@H](O1)N1CN(C=2C(=O)NC(N)=NC12)C)O | I[CH3:1].[n:2]1[cH:3][n:4]([C@@H:5]2[O:6][C@H:7]([CH2:8][O:9][P:10](=[O:11])([OH:12])[O:13][P:14](=[O:15])([OH:16])[OH:17])[CH2:18][C@H:19]2[OH:20])[c:21]2[n:22][c:23]([NH2:24])[nH:25][c:26](=[O:27])[c:28]12>>[CH3:1][N:2]1[CH2:3][N:4]([C@@H:5]2[O:6][C@H:7]([CH2:8][O:9][P:10](=[O:11])([OH:12])[O:13][P:14](=[O:15])([OH:1... | CI.Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)C[C@H]2O)c(=O)[nH]1 | CN1CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)C[C@H]2O)c2nc(N)[nH]c(=O)c21 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 453754ef287fc029322172b1bf659dbe63368ea842b9469692b1922396d9e73d | c85e543f4fd209b9b10885d7f60ab6a5ddf2a0681bb917a6d26f16908906d83b | O=c1[nH]cnc2c1NCN2[C@H]1CCCO1 | I-[CH3;D1;+0:1].[C:2]-[C:3](-[n;H0;D3;+0:4]1:[cH;D2;+0:5]:[n;H0;D2;+0:6]:[c:7]2:[c:8]:1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:2=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:2]-[C:3](-[N;H0;D3;+0:4]1-[CH2;D2;+0:5]-[N;H0;D3;+0:6](-[CH3;D1;+0:1])-[c:7]2:[c:8]-1:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:2=[O;D1;H0:13])-[#8:14]-[C:15] | 28 | [{"value": 28.0, "product": "P(O)(=O)(OP(=O)(O)O)OC[C@@H]1C[C@H]([C@@H](O1)N1CN(C=2C(=O)NC(N)=NC12)C)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound 5 (34 mg, 0.055 mmol) was mixed with 1 mL of dimethylsulfoxide, 1 mL of DMF, and 100 μL of methyl iodide at room temperature. After 3 h the reaction mixture was treated with 30 mL of cold water and extracted three times with 10-mL portions of diethyl ether. After neutralization with NaHCO3, chromatographic sep... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine.Tertiary amine | c1ncc2[nH]cnc2n1 | c1ncc2c(n1)NCN2 | C1CCOC1.c1ncc2c(n1)NCN2 | I- | O | null | null | CI.Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)C[C@H]2O)c(=O)[nH]1>O>CN1CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)C[C@H]2O)c2nc(N)[nH]c(=O)c21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0bd35f1dbed94cb695d4a4bbb4cd503e | CN1CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)C[C@H]2O)c2nc(N)[nH]c(=O)c21>>Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)C[C@H]2O)c(=O)[nH]1 | C(=O)(O)[O-].[Na+].P(O)(=O)(OP(=O)(O)O)OC[C@@H]1C[C@H]([C@@H](O1)N1CN(C=2C(=O)NC(N)=NC12)C)O.C(CN(CC(=O)O)CC(=O)O)N(CC(=O)O)CC(=O)O>>P(O)(=O)(OP(=O)(O)O)OC[C@@H]1C[C@H]([C@@H](O1)N1C=NC=2C(=O)NC(N)=NC12)O | C[N:6]1[c:5]2[c:4]([n:3][c:2]([NH2:1])[nH:27][c:25]2=[O:26])[N:8]([C@@H:9]2[O:10][C@H:11]([CH2:12][O:13][P:14](=[O:15])([OH:16])[O:17][P:18](=[O:19])([OH:20])[OH:21])[CH2:22][C@H:23]2[OH:24])[CH2:7]1>>[NH2:1][c:2]1[n:3][c:4]2[c:5]([n:6][cH:7][n:8]2[C@@H:9]2[O:10][C@H:11]([CH2:12][O:13][P:14](=[O:15])([OH:16])[O:17][P:1... | CN1CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)C[C@H]2O)c2nc(N)[nH]c(=O)c21 | Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)C[C@H]2O)c(=O)[nH]1 | null | [Cl-].[Cl-].[Zn+2] | O.CN(C)C=O | Miscellaneous | OtherReaction | 298d35e2eff25f5688105434c1398a56fd2f8efb335d8d4f0df65222f9ffb433 | abf0fa8ff387957ab6b76afc2c917d99e43e57de4619924b4d2a678ed546b1a1 | O=c1[nH]cnc2c1ncn2[C@H]1CCCO1 | C-[N;H0;D3;+0:1]1-[CH2;D2;+0:2]-[N;H0;D3;+0:3](-[C:4](-[C:5])-[#8:6]-[C:7])-[c:8]2:[#7;a:9]:[c:10]:[#7;a:11]:[c:12](=[O;D1;H0:13]):[c:14]:2-1>>[C:7]-[#8:6]-[C:4](-[n;H0;D3;+0:3]1:[cH;D2;+0:2]:[n;H0;D2;+0:1]:[c:14]2:[c:12](=[O;D1;H0:13]):[#7;a:11]:[c:10]:[#7;a:9]:[c:8]:2:1)-[C:5] | null | [] | null | null | 8 | HOUR | GMP (purchased from Sigma, converted to the TEA salt, 29 mg, 0.05 mmol), imidazole (17 mg, 0.25 mmol), and 2,2′-dithiodipyridine (22 mg, 0.1 mmol, purchased from Aldrich) were mixed in anhydrous DMF (1.2 mL) and TEA (7 μL). Triphenylphosphine (26 mg, 0.1 mmol) was added, and the mixture was stirred for 5 h at room temp... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine.Tertiary amine | null | c1ncc2c(n1)NCN2 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1CCOC1 | Other | [Cl-].[Cl-].[Zn+2].O.CN(C)C=O | null | 8 | CN1CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)C[C@H]2O)c2nc(N)[nH]c(=O)c21>[Cl-].[Cl-].[Zn+2].O.CN(C)C=O>Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)C[C@H]2O)c(=O)[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-285f84bea00e4a3ea1eb36053e52c544 | CN(C)C=O.Clc1ccnc(Cl)c1>>O=Cc1c(Cl)ccnc1Cl | [Cl-].[NH4+].ClC1=NC=CC(=C1)Cl.C(C)(C)[N-]C(C)C.[Li+].CN(C=O)C>>ClC1=NC=CC(=C1C=O)Cl | CN(C)[CH:2]=[O:1].[cH:3]1[c:4]([Cl:5])[cH:6][cH:7][n:8][c:9]1[Cl:10]>>[O:1]=[CH:2][c:3]1[c:4]([Cl:5])[cH:6][cH:7][n:8][c:9]1[Cl:10] | CN(C)C=O.Clc1ccnc(Cl)c1 | O=Cc1c(Cl)ccnc1Cl | null | null | O1CCCC1.O.C(Cl)Cl | C-C Coupling | OtherReaction | fdadf445bc7330d90b7bd9b20fa76e9137f072d7efd4f8187f2f956f7d29eb78 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccncc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[Cl;D1;H0:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8](-[Cl;D1;H0:9]):[cH;D2;+0:10]:1>>[Cl;D1;H0:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8](-[Cl;D1;H0:9]):[c;H0;D3;+0:10]:1-[CH;D2;+0:1]=[O;D1;H0:2] | null | [] | null | null | 3 | HOUR | Under nitrogen, a solution of 1.6 g of 2,4-dichloropyridine in 5 mL dry tetrahydrofuran (THF) was added to a solution of 6 mL of lithium diisopropyl amide in 25 mL of THF at −70° C., followed by stirring at this temperature for 3 hours. Then 1 mL of dry N,N-dimethylformamide was added at −70° C. followed by stirring at... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | O1CCCC1.O.C(Cl)Cl | null | 3 | CN(C)C=O.Clc1ccnc(Cl)c1>O1CCCC1.O.C(Cl)Cl>O=Cc1c(Cl)ccnc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2d0e35ce77454d3dba4f66033a8045cb | NS(=O)(=O)O.O=Cc1c(Cl)ccnc1Cl>>O=C(O)c1c(Cl)ccnc1Cl | Cl(=O)[O-].[Na+].S(N)(O)(=O)=O.ClC1=NC=CC(=C1C=O)Cl>>ClC1=C(C(=O)O)C(=CC=N1)Cl | NS(=O)(=O)[OH:3].[O:1]=[CH:2][c:4]1[c:5]([Cl:6])[cH:7][cH:8][n:9][c:10]1[Cl:11]>>[O:1]=[C:2]([OH:3])[c:4]1[c:5]([Cl:6])[cH:7][cH:8][n:9][c:10]1[Cl:11] | NS(=O)(=O)O.O=Cc1c(Cl)ccnc1Cl | O=C(O)c1c(Cl)ccnc1Cl | null | null | O.[OH-].[Na+].C1CCOC1 | Acylation | OtherReaction | f287b39bba0c1b0397a4f00e499125db790c794585d77f89499d60ab3c26798d | a8ae608e736a38cb1830db0bc435afaf4aadee39cc7dd85eee29358304f341fb | c1ccncc1 | N-S(=O)(=O)-[OH;D1;+0:1].[Cl;D1;H0:2]-[c:3](:[#7;a:4]:[c:5]):[c:6](-[CH;D2;+0:7]=[O;D1;H0:8]):[c:9]>>[Cl;D1;H0:2]-[c:3](:[#7;a:4]:[c:5]):[c:6](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[OH;D1;+0:1]):[c:9] | 50.4 | [{"value": 50.4, "product": "ClC1=C(C(=O)O)C(=CC=N1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 0.40 g of the aldehyde from Step B was dissolved in 6 mL of THF and then added to a solution of 0.27 g of sodium chlorite and 0.29 g of sulfamic acid in 6 mL of water. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with 1 N sodium hydroxide (10 mL) and ext... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aldehyde | Carboxylic acid | null | null | c1ccncc1 | HO- | O.[OH-].[Na+].C1CCOC1 | null | 8 | NS(=O)(=O)O.O=Cc1c(Cl)ccnc1Cl>O.[OH-].[Na+].C1CCOC1>O=C(O)c1c(Cl)ccnc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8ee93a0b463c4dbb86a4cad82feafe87 | NCc1ncc(C(F)(F)F)cc1Cl.O=C(O)c1c(Cl)ccnc1Cl>>O=C(NCc1ncc(C(F)(F)F)cc1Cl)c1c(Cl)ccnc1Cl | ClC1=C(C(=O)O)C(=CC=N1)Cl.Cl.NCC1=NC=C(C=C1Cl)C(F)(F)F.C(C)N(CC)CC>>ClC1=NC=CC(=C1C(=O)NCC1=NC=C(C=C1Cl)C(F)(F)F)Cl | [NH2:3][CH2:4][c:5]1[n:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]1[Cl:15].O[C:2](=[O:1])[c:16]1[c:17]([Cl:18])[cH:19][cH:20][n:21][c:22]1[Cl:23]>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[n:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]1[Cl:15])[c:16]1[c:17]([Cl:18])[cH:19][cH:20][n:21][c:22]1[Cl:23] | NCc1ncc(C(F)(F)F)cc1Cl.O=C(O)c1c(Cl)ccnc1Cl | O=C(NCc1ncc(C(F)(F)F)cc1Cl)c1c(Cl)ccnc1Cl | null | null | S(=O)(Cl)Cl.C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCc1ccccn1)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8].[#7;a:9]:[c:10]-[C:11]-[NH2;D1;+0:12]>>[#7;a:9]:[c:10]-[C:11]-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8] | null | [] | null | null | 8 | HOUR | A solution of 0.22 g of the acid from Step C was refluxed in thionyl chloride for 1 hour followed by removal of the solvent under vacuum to give an oil. The oil was dissolved in 1 mL of methylene chloride and added to a solution of 2-aminomethyl-3-chloro-5-trifluoromethylpyridine hydrochloride (0.25 g) and triethylamin... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccncc1 | HO- | S(=O)(Cl)Cl.C(Cl)Cl | null | 8 | NCc1ncc(C(F)(F)F)cc1Cl.O=C(O)c1c(Cl)ccnc1Cl>S(=O)(Cl)Cl.C(Cl)Cl>O=C(NCc1ncc(C(F)(F)F)cc1Cl)c1c(Cl)ccnc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a3080e5880ff42ab9444ce4821a81d0d | CCOC(=O)CN=C(c1ccccc1)c1ccccc1.CI.FC(F)(F)c1cnc(Cl)c(Cl)c1>>CC(N)c1ncc(C(F)(F)F)cc1Cl | CI.C(C)OC(CN=C(C1=CC=CC=C1)C1=CC=CC=C1)=O.[H-].[Na+].C([O-])([O-])=O.[Na+].[Na+].ClC1=NC=C(C=C1Cl)C(F)(F)F>>ClC=1C(=NC=C(C1)C(F)(F)F)C(N)C | CCOC(=O)[CH2:2][N:3]=C(c1ccccc1)c1ccccc1.I[CH3:1].Cl[c:4]1[n:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][c:13]1[Cl:14]>>[CH3:1][CH:2]([NH2:3])[c:4]1[n:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][c:13]1[Cl:14] | CCOC(=O)CN=C(c1ccccc1)c1ccccc1.CI.FC(F)(F)c1cnc(Cl)c(Cl)c1 | CC(N)c1ncc(C(F)(F)F)cc1Cl | null | null | Cl.CN(C=O)C | C-C Coupling | OtherReaction | 26e08ea7caef6cb4073aa081a2f046eca76795d0aa7419697914ad53218a2e59 | e9a2455378990d04facbca7856ccce224cff919e24b8d3142758c0d29a976781 | c1ccncc1 | C-C-O-C(=O)-[CH2;D2;+0:1]-[N;H0;D2;+0:2]=C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.Cl-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[c:6](-[Cl;D1;H0:7]):[c:8].I-[CH3;D1;+0:9]>>[CH3;D1;+0:9]-[CH;D3;+0:1](-[NH2;D1;+0:2])-[c;H0;D3;+0:3](:[#7;a:4]:[c:5]):[c:6](-[Cl;D1;H0:7]):[c:8] | 79.3 | [{"value": 79.3, "product": "ClC=1C(=NC=C(C1)C(F)(F)F)C(N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | N-(diphenylmethylene)glycine ethyl ester (2.25 g) was added to a suspension of sodium hydride (0.74 g of 60% oil dispersion) in 20 mL of dry N,N-dimethylformamide at room temperature, resulting in vigorous gas evolution. After stirring at room temperature for five minutes, 2 g of 2,3-dichloro-5-trifluoromethylpyridine ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Substituted imine | Primary amine | c1ccccc1.c1ccccc1.c1ccncc1 | c1ccncc1 | c1ccncc1 | HCl.I- | Cl.CN(C=O)C | null | 0.083333 | CCOC(=O)CN=C(c1ccccc1)c1ccccc1.CI.FC(F)(F)c1cnc(Cl)c(Cl)c1>Cl.CN(C=O)C>CC(N)c1ncc(C(F)(F)F)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b92e03430ce64cfd8549db8cb98d780c | CC(N)c1ncc(C(F)(F)F)cc1Cl.O=C(Cl)c1c(Cl)ccnc1Cl>>CC(NC(=O)c1c(Cl)ccnc1Cl)c1ncc(C(F)(F)F)cc1Cl | ClC1=C(C(=O)Cl)C(=CC=N1)Cl.ClC=1C(=NC=C(C1)C(F)(F)F)C(N)C.C(C)N(CC)CC>>ClC1=NC=CC(=C1C(=O)NC(C)C1=NC=C(C=C1Cl)C(F)(F)F)Cl | [CH3:1][CH:2]([NH2:3])[c:14]1[n:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][c:23]1[Cl:24].Cl[C:4](=[O:5])[c:6]1[c:7]([Cl:8])[cH:9][cH:10][n:11][c:12]1[Cl:13]>>[CH3:1][CH:2]([NH:3][C:4](=[O:5])[c:6]1[c:7]([Cl:8])[cH:9][cH:10][n:11][c:12]1[Cl:13])[c:14]1[n:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][c... | CC(N)c1ncc(C(F)(F)F)cc1Cl.O=C(Cl)c1c(Cl)ccnc1Cl | CC(NC(=O)c1c(Cl)ccnc1Cl)c1ncc(C(F)(F)F)cc1Cl | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1ccccn1)c1cccnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8].[#7;a:9]:[c:10]-[C:11](-[C;D1;H3:12])-[NH2;D1;+0:13]>>[#7;a:9]:[c:10]-[C:11](-[C;D1;H3:12])-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8] | null | [] | null | null | 8 | HOUR | 2,4-Dichloronicotinoyl chloride (0.40 g), made as in Example 1, Step C, was added to a solution of the amine intermediate from Step A (0.66 g) and triethylamine (0.70 g) in 30 mL of methylene chloride at room temperature followed by stirring overnight. The reaction mixture was distilled under vacuum to remove the solve... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccncc1 | HCl | C(Cl)Cl | null | 8 | CC(N)c1ncc(C(F)(F)F)cc1Cl.O=C(Cl)c1c(Cl)ccnc1Cl>C(Cl)Cl>CC(NC(=O)c1c(Cl)ccnc1Cl)c1ncc(C(F)(F)F)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6a4dd3eb78ac4e96a9746bc45aadf081 | CCOC(=O)CN=C(c1ccccc1)c1ccccc1.CI.Clc1cc(Br)cnc1Cl>>CC(N)c1ncc(Br)cc1Cl.Cl | CI.BrC=1C=C(C(=NC1)Cl)Cl.[H-].[Na+].C(C)OC(CN=C(C1=CC=CC=C1)C1=CC=CC=C1)=O>>Cl.BrC=1C=C(C(=NC1)C(N)C)Cl | CCOC(=O)[CH2:2][N:3]=C(c1ccccc1)c1ccccc1.I[CH3:1].[c:4]1([Cl:12])[n:5][cH:6][c:7]([Br:8])[cH:9][c:10]1[Cl:11]>>[CH3:1][CH:2]([NH2:3])[c:4]1[n:5][cH:6][c:7]([Br:8])[cH:9][c:10]1[Cl:11].[ClH:12] | CCOC(=O)CN=C(c1ccccc1)c1ccccc1.CI.Clc1cc(Br)cnc1Cl | CC(N)c1ncc(Br)cc1Cl.Cl | null | null | O.CN(C=O)C | C-C Coupling | OtherReaction | 26e08ea7caef6cb4073aa081a2f046eca76795d0aa7419697914ad53218a2e59 | e9a2455378990d04facbca7856ccce224cff919e24b8d3142758c0d29a976781 | c1ccncc1 | C-C-O-C(=O)-[CH2;D2;+0:1]-[N;H0;D2;+0:2]=C(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.I-[CH3;D1;+0:3].[Cl;D1;H0:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[Cl;H0;D1;+0:8]):[#7;a:9]:[c:10]>>[CH3;D1;+0:3]-[CH;D3;+0:1](-[NH2;D1;+0:2])-[c;H0;D3;+0:7](:[#7;a:9]:[c:10]):[c:5](-[Cl;D1;H0:4]):[c:6].[ClH;D0;+0:8] | 27.8 | [{"value": 27.8, "product": "Cl.BrC=1C=C(C(=NC1)C(N)C)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | Under nitrogen, 4.1 g of the title compound from Step B was added to a suspension of sodium hydride (60% oil suspension) in 30 mL of dry N,N-dimethylformamide, cooled to 0° C. N-(Diphenylmethylene)glycine ethyl ester (4.6 g) was added in portions with no exotherm, and the mixture was stirred at room temperature for 3 h... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Substituted imine | Primary amine | c1ccccc1.c1ccccc1.c1ccncc1 | c1ccncc1 | c1ccncc1 | HI | O.CN(C=O)C | 0 | 3 | CCOC(=O)CN=C(c1ccccc1)c1ccccc1.CI.Clc1cc(Br)cnc1Cl>O.CN(C=O)C>CC(N)c1ncc(Br)cc1Cl.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b7526cb3c00b4321a5b9b0c612c6bbab | CC(N)c1ncc(Br)cc1Cl.O=C(Cl)c1c(Cl)ccnc1Cl>>CC(NC(=O)c1c(Cl)ccnc1Cl)c1ncc(Br)cc1Cl | Cl.BrC=1C=C(C(=NC1)C(N)C)Cl.C(C)N(CC)CC.ClC1=C(C(=O)Cl)C(=CC=N1)Cl>>BrC=1C=C(C(=NC1)C(C)NC(=O)C=1C(=NC=CC1Cl)Cl)Cl | [CH3:1][CH:2]([NH2:3])[c:14]1[n:15][cH:16][c:17]([Br:18])[cH:19][c:20]1[Cl:21].Cl[C:4](=[O:5])[c:6]1[c:7]([Cl:8])[cH:9][cH:10][n:11][c:12]1[Cl:13]>>[CH3:1][CH:2]([NH:3][C:4](=[O:5])[c:6]1[c:7]([Cl:8])[cH:9][cH:10][n:11][c:12]1[Cl:13])[c:14]1[n:15][cH:16][c:17]([Br:18])[cH:19][c:20]1[Cl:21] | CC(N)c1ncc(Br)cc1Cl.O=C(Cl)c1c(Cl)ccnc1Cl | CC(NC(=O)c1c(Cl)ccnc1Cl)c1ncc(Br)cc1Cl | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1ccccn1)c1cccnc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8].[#7;a:9]:[c:10]-[C:11](-[C;D1;H3:12])-[NH2;D1;+0:13]>>[#7;a:9]:[c:10]-[C:11](-[C;D1;H3:12])-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8] | null | [] | null | null | 8 | HOUR | The product of Step C (0.80 g), 1.21 mL of triethyl amine and 0.62 g of 2,4-dichloronicotinoyl chloride were combined in that order at <20° C. in 25 mL of methylene chloride, and the mixture was stirred at room temperature overnight. The reaction mixture was reduced in vacuo to produce the title compound, a compound of... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccncc1 | HCl | C(Cl)Cl | null | 8 | CC(N)c1ncc(Br)cc1Cl.O=C(Cl)c1c(Cl)ccnc1Cl>C(Cl)Cl>CC(NC(=O)c1c(Cl)ccnc1Cl)c1ncc(Br)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-85b8f75242994a83a1b336b69db37d20 | O=P([O-])(O)O.[OH-]>>O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] | [Cl-].[K+].OP(=O)(O)[O-].[K+].Cl.[Cl-].[Cl-].[Ca+2].[OH-].[K+]>>P(=O)([O-])([O-])[O-].[Ca+2].P(=O)([O-])([O-])[O-].[Ca+2].[Ca+2] | [O:1]=[P:2]([O-:3])([OH:4])[OH:5].[OH-:6]>>[O:1]=[P:2]([O-:3])([O-:4])[O-:5].[O:6]=[P:7]([O-:8])([O-:9])[O-:10].[Ca+2:12].[Ca+2:13] | O=P([O-])(O)O.[OH-] | O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] | null | null | O | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | null | [O;-;D1;H0:1]-[#15:2](=[O;D1;H0:3])(-[OH;D1;+0:4])-[OH;D1;+0:5].[OH-;D0:6]>>[O-;H0;D1:4]-[#15:2](-[O-;H0;D1:5])(-[O;-;D1;H0:1])=[O;D1;H0:3].[O;-;D1;H0:7]-[#15:8](-[O;-;D1;H0:9])(-[O;-;D1;H0:10])=[O;H0;D1;+0:6] | null | [] | 22 | CELSIUS | 2 | DAY | Combine in a suitable vessel, 2.1M KCl (35 mL), 0.0175M CaCl2 (5 mL), 0.01M KH2PO4 (50mL), and de-ionized water (350 mL). A standard pH electrode equipped with a Standard Calomel Reference electrode is inserted and the temperature adjusted to 37° C. while purging of the solution of oxygen. Once the temperature and pH a... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | 22 | 48 | O=P([O-])(O)O.[OH-]>O>O=P([O-])([O-])[O-].O=P([O-])([O-])[O-].[Ca+2].[Ca+2] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7b9226836db4409dbcfc79f86487971f | CC(O)S.CCCCCCCCCCBr>>CCCCCCCCCCSC(C)O | C([O-])([O-])=O.[K+].[K+].C(CCCCCCCCC)Br.SC(C)O>>C(CCCCCCCCC)SC(C)O | [SH:11][CH:12]([CH3:13])[OH:14].Br[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][S:11][CH:12]([CH3:13])[OH:14] | CC(O)S.CCCCCCCCCCBr | CCCCCCCCCCSC(C)O | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 77cd742b5ba20df0e225494f6e5f3d958ee82ce9a1b16fd99a2d9f8350b4fdc8 | b05f7dda7dad719ae1868a84c33eeaf5bf649036fc64173cf4774a5eb4d70181 | null | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[C:5](-[O;D1;H1:6])-[SH;D1;+0:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:7]-[C:5](-[C;D1;H3:4])-[O;D1;H1:6] | 94 | [{"value": 94.0, "product": "C(CCCCCCCCC)SC(C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | Under nitrogen, to a suspension of potassium carbonate (27 g, 200 mmol) in acetone (100 ml) was added decyl bromide (10 ml, 50 mmol) and mercaptoethanol (4.4 ml, 63 mmol). The suspension was stirred at room temperature for 2 days, then partitioned between water and 80% hexane/ethyl acetate. The organic phase was washed... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aliphatic thiol | Monosulfide | null | null | null | HBr | CC(=O)C | null | 48 | CC(O)S.CCCCCCCCCCBr>CC(=O)C>CCCCCCCCCCSC(C)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0204cf93123c41c482663dcdcd943259 | COC(=O)c1ccc(C)c(Cl)c1.O=C1CCC(=O)N1Br>>COC(=O)c1ccc(CBr)c(Cl)c1 | ClC=1C=C(C(=O)OC)C=CC1C.C1CC(=O)N(C1=O)Br.CC(C)(C#N)N=NC(C)(C)C#N>>BrCC1=C(C=C(C(=O)OC)C=C1)Cl | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:11]([Cl:12])[cH:13]1.O=C1CCC(=O)N1[Br:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][Br:10])[c:11]([Cl:12])[cH:13]1 | COC(=O)c1ccc(C)c(Cl)c1.O=C1CCC(=O)N1Br | COC(=O)c1ccc(CBr)c(Cl)c1 | 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] | null | [] | null | null | null | null | To a solution of methyl 3-chloro-4-methylbenzoate (5.0 g, 27.1 mmol) in carbon tetrachloride (50 ml) were added NBS (5.8 g, 32.0 mmol) and AIBN (0.442 g, 2.70 mmol). The mixture was stirred at reflux for 18 h. The mixture was allowed to cool to room temperature and then concentrated in vacuo. The residue was purified b... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | COC(=O)c1ccc(C)c(Cl)c1.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>COC(=O)c1ccc(CBr)c(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-074409887c6b4491915eaa7115f068c1 | Cc1cc(Br)ccc1C#N.O=C=O>>Cc1cc(C(=O)O)ccc1C#N | BrC1=CC(=C(C#N)C=C1)C.C(CCC)[Li].C(=O)=O.O>>C(#N)C1=C(C=C(C(=O)O)C=C1)C | Br[c:4]1[cH:3][c:2]([CH3:1])[c:10]([C:11]#[N:12])[cH:9][cH:8]1.[C:5](=[O:6])=[O:7]>>[CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[OH:7])[cH:8][cH:9][c:10]1[C:11]#[N:12] | Cc1cc(Br)ccc1C#N.O=C=O | Cc1cc(C(=O)O)ccc1C#N | null | null | C1CCOC1 | Acylation | OtherReaction | 07ac4a201d363784a28677e85b547e572f4793f5010c94050885192cae13600e | d0d963f3850574b1f0fda744314036458b2dd627cb0c4e2f893b9c52a88ad449 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C;H0;D2;+0:7]=[O;H0;D1;+0:8]>>[O;D1;H0:6]=[C;H0;D3;+0:7](-[OH;D1;+0:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | -78 | CELSIUS | 1 | HOUR | To a solution of 4-bromo-2-methylbenzonitrile (2.0 g, 10.2 mmol) in THF (100 ml) at −78° C. under a nitrogen atmosphere was added dropwise a 2.5M solution of n-butyl lithium (4.48 ml, 11.2 mmol). The mixture was stirred at −78° C. for 1 h and then poured onto solid carbon dioxide (5 g) in THF (50 ml). The mixture was a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbon dioxide | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | C1CCOC1 | -78 | 1 | Cc1cc(Br)ccc1C#N.O=C=O>C1CCOC1>Cc1cc(C(=O)O)ccc1C#N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bb307fc894aa47c9b5892e951dbd34e2 | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O.CNC>>C[N-]C.O=C(O)[C@@H]1C[C@@H](O)CN1 | C(=O)(OC(C)(C)C)N1[C@H](C(=O)O)C[C@@H](O)C1.C(C)(C)N(C(C)C)CC.Cl.CNC>>C1[C@H](CN[C@@H]1C(=O)O)O.Cl.C[N-]C | CC(C)(C)OC(=O)[N:13]1[C@H:8]([C:6](=[O:5])[OH:7])[CH2:9][C@@H:10]([OH:11])[CH2:12]1.[CH3:1][NH:2][CH3:3]>>[CH3:1][N-:2][CH3:3].[O:5]=[C:6]([OH:7])[C@@H:8]1[CH2:9][C@@H:10]([OH:11])[CH2:12][NH:13]1 | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O.CNC | C[N-]C.O=C(O)[C@@H]1C[C@@H](O)CN1 | null | CN(C1=CC=NC=C1)C | ClCCl.Cl.O1CCOCC1 | Miscellaneous | OtherReaction | bb26b59b25b2aff8252cc85db25a312e509af21febf6ff44a37d46b4e518d6e9 | 06253d29486db69546b3461eb2ce8d291a76aee5f42427de5b29b705e0a811fc | C1CCNC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6](=[O;D1;H0:7])-[O;D1;H1:8].[C;D1;H3:9]-[NH;D2;+0:10]-[C;D1;H3:11]>>[C;D1;H3:9]-[N-;H0;D2:10]-[C;D1;H3:11].[O;D1;H0:7]=[C:6](-[O;D1;H1:8])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | null | null | 30 | HOUR | To a solution of BOC-hydroxyproline (2.99 g, 13.89 mmol) in dichloromethane (100 ml) were added N,N-diisopropylethylamine (3.7 ml, 21.24 mmol), 4-(dimethylamino)pyridine (1.74 g, 14.24 mmol), dimethylamine hydrochloride (1.72 g, 21.09 mmol) and WSCDI (3.17 g, 16.68 mmol). The mixture was stirred at room temperature for... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Secondary amine.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1CCNC1 | HO- | CN(C1=CC=NC=C1)C.ClCCl.Cl.O1CCOCC1 | null | 30 | CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1C(=O)O.CNC>CN(C1=CC=NC=C1)C.ClCCl.Cl.O1CCOCC1>C[N-]C.O=C(O)[C@@H]1C[C@@H](O)CN1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d413e2e553a4450385370e823e4fa83a | Nc1ccc([As](=O)(O)O)cc1.O=C(Br)CBr>>O=C(CBr)Nc1ccc([As](=O)(O)O)cc1 | C([O-])([O-])=O.C1=CC(=CC=C1N)[As](=O)(O)O.BrCC(=O)Br.C(=O)=O.C([O-])([O-])=O.[Na+].[Na+].BrCC(=O)Br.S(O)(O)(=O)=O>>BrCC(=O)NC1=CC=C(C=C1)[As](O)(O)=O | [NH2:5][c:6]1[cH:7][cH:8][c:9]([As:10](=[O:11])([OH:12])[OH:13])[cH:14][cH:15]1.Br[C:2](=[O:1])[CH2:3][Br:4]>>[O:1]=[C:2]([CH2:3][Br:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([As:10](=[O:11])([OH:12])[OH:13])[cH:14][cH:15]1 | Nc1ccc([As](=O)(O)O)cc1.O=C(Br)CBr | O=C(CBr)Nc1ccc([As](=O)(O)O)cc1 | null | null | ClCCl.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Br-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Br;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[Br;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 2.5 | HOUR | Sodium carbonate (40.14 g, 378.7 mmol) was added to water (200 mL) and stirred at room temperature until all solids had dissolved. To the stirred carbonate solution was added p-arsanilic acid (29.99 g, 138.2 mmol), portionwise, and the volume of the solution made up to 300 mL with addition of more water. The solution (... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HBr | ClCCl.O | null | 2.5 | Nc1ccc([As](=O)(O)O)cc1.O=C(Br)CBr>ClCCl.O>O=C(CBr)Nc1ccc([As](=O)(O)O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7de85a4229cb46598044063bcdac42a6 | O=C([O-])CC[C@H](NC(=O)CCS)C(=O)[O-].O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CC(=O)O)C(=O)O)cc1>>O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 | [As](=O)C1=CC=C(C=C1)NC(=O)CSCCC(=O)N[C@@H](CC(=O)O)C(=O)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.SCCC(=O)N[C@@H](CCC(=O)[O-])C(=O)[O-].[Na+].[Na+].C([O-])(O)=O>>[As](=O)C1=CC=C(C=C1)NC(=O)CSCCC(=O)N[C@@H](CCC(=O)O)C(=O)O | O=C(CCS)N[C@H](C(=O)[O-])[CH2:18][CH2:19][C:20](=[O:21])[O-:22].O=C(O)C[C@H:17]([NH:16][C:14]([CH2:13][CH2:12][S:11][CH2:10][C:8]([NH:7][c:6]1[cH:5][cH:4][c:3]([As:2]=[O:1])[cH:27][cH:26]1)=[O:9])=[O:15])[C:23](=[O:24])[OH:25]>>[O:1]=[As:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[CH2:10][S:11][CH2:12][CH2:13][C:14](... | O=C([O-])CC[C@H](NC(=O)CCS)C(=O)[O-].O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CC(=O)O)C(=O)O)cc1 | O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 | null | null | CS(=O)C | C-C Coupling | OtherReaction | 27df6118213d0a186385ca2c07812d6bde0c77fb447f8e5ba884d3fa9fc2c7c8 | 4a0ad09b2376324fd5f347eb80435967738ca7e434f5634c3eca7157b018355a | c1ccccc1 | O-C(=O)-C-[C@H;D3;+0:1](-[#7:2]-[C:3](-[C:4])=[O;D1;H0:5])-[C:6](=[O;D1;H0:7])-[O;D1;H1:8].O=C(-C-C-S)-N-[C@H](-[CH2;D2;+0:9]-[C:10]-[C:11](-[O-;H0;D1:12])=[O;D1;H0:13])-C(=O)-[O-]>>[C:4]-[C:3](=[O;D1;H0:5])-[#7:2]-[C@@H;D3;+0:1](-[CH2;D2;+0:9]-[C:10]-[C:11](=[O;D1;H0:13])-[OH;D1;+0:12])-[C:6](=[O;D1;H0:7])-[O;D1;H1:8] | null | [] | null | null | null | null | The procedure used was the same as for N-(3-(4-arsenosophenylcarbamoylmethylthio)-propanoyl)-L-aspartic acid, using 2.63 mL (184 μmol) of 70.0 mM BRAO in DMSO, the disulfide of disodium N-(3-mercaptopropanoyl)-L-glutamate (0.61 g), 0.5 M bicarbonate buffer, pH 9 (10.52 mL, 5.3 mmol), and 0.69 M triphenylphosphine in DM... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amide.Aliphatic thiol | Carboxylic acid | null | null | c1ccccc1 | Other | CS(=O)C | null | null | O=C([O-])CC[C@H](NC(=O)CCS)C(=O)[O-].O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CC(=O)O)C(=O)O)cc1>CS(=O)C>O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e022ca322de149b8949ce4695c0de88c | O=C(CCS)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O.O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1>>O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@H]2C(O)O[C@H](CO)[C@@H](O)[C@@H]2O)cc1 | [As](=O)C1=CC=C(C=C1)NC(=O)CSCCC(=O)N[C@@H](CCC(=O)O)C(=O)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.SCCC(=O)N[C@H]1C(O)O[C@@H]([C@H]([C@@H]1O)O)CO.[Na].[Na].C([O-])(O)=O>>[As](=O)C1=CC=C(C=C1)NC(=O)CSCCC(=O)N[C@H]1C(O)O[C@@H]([C@H]([C@@H]1O)O)CO | O=C(CCS)[NH:16][C@H:17]1[CH:18]([OH:19])[O:20][C@H:21]([CH2:22][OH:23])[C@@H:24]([OH:25])[C@@H:26]1[OH:27].O=C(O)CC[C@H](N[C:14]([CH2:13][CH2:12][S:11][CH2:10][C:8]([NH:7][c:6]1[cH:5][cH:4][c:3]([As:2]=[O:1])[cH:29][cH:28]1)=[O:9])=[O:15])C(=O)O>>[O:1]=[As:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[CH2:10][S:11][CH2... | O=C(CCS)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O.O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 | O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@H]2C(O)O[C@H](CO)[C@@H](O)[C@@H]2O)cc1 | null | null | CS(=O)C | Acylation | OtherReaction | 36506d5556b04762dba6d7c1cd60be5c7bff26fb8832038c2f0dd5528c975f1c | 0e1078419ee18e1670d05b07c6b68c5e4f56a22cbc2db8c51866c068bd88bea7 | O=C(CSCCC(=O)N[C@@H]1CCCOC1)Nc1ccccc1 | O-C(=O)-C-C-[C@H](-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4])-C(-O)=O.O=C(-C-C-S)-[NH;D2;+0:5]-[C:6](-[C:7])-[C:8]-[#8:9]>>[#8:9]-[C:8]-[C:6](-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4])-[C:7] | null | [] | null | null | null | null | The procedure used was the same as for N-(3-(4-arsenosophenylcarbamoylmethylthio)propanoyl)-L-glutamic acid, using 3.00 mL (210 μmol) of 70.0 mM BRAO in DMSO, the disulfide of disodium N-(3-mercaptopropanoyl)-D-glucosamine (0.67 g), 0.5 M bicarbonate buffer, pH 9 (11.96 mL, 6.0 mmol), and 0.69 M triphenylphosphine in D... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Secondary amide.Secondary amide.Aliphatic thiol | Secondary amide | null | null | c1ccccc1.C1CCOCC1 | Other | CS(=O)C | null | null | O=C(CCS)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O.O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1>CS(=O)C>O=[As]c1ccc(NC(=O)CSCCC(=O)N[C@H]2C(O)O[C@H](CO)[C@@H](O)[C@@H]2O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-edf9fdfcefd14954ae03271d59898a8b | O=[N+]([O-])c1ccccc1Br.OB(O)c1ccc(Cl)cc1>>O=[N+]([O-])c1ccccc1-c1ccc(Cl)cc1 | BrC1=C(C=CC=C1)[N+](=O)[O-].ClC1=CC=C(C=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>ClC1=CC=C(C=C1)C1=C(C=CC=C1)[N+](=O)[O-] | Br[c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][cH:8]1.OB(O)[c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]1 | O=[N+]([O-])c1ccccc1Br.OB(O)c1ccc(Cl)cc1 | O=[N+]([O-])c1ccccc1-c1ccc(Cl)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C(C)O.C1CCOC1 | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[c:2]:[c:3] | 86.5 | [{"value": 86.5, "product": "ClC1=CC=C(C=C1)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of 2-bromonitrobenzene (646 mg) in THF (17 ml) under nitrogen was added tetrakis(triphenylphosphine)palladium (0) (900 mg). The resulting mixture was stirred at room temperature for 20 min, then a solution of 4-chlorophenylboronic acid (1.0 g) in ethanol (17 ml) was added and the resulting mixture stirred... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)O.C1CCOC1 | null | 0.333333 | O=[N+]([O-])c1ccccc1Br.OB(O)c1ccc(Cl)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(C)O.C1CCOC1>O=[N+]([O-])c1ccccc1-c1ccc(Cl)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f9a24497068a44d3b7a4d3c13a5cca3f | O=[N+]([O-])c1ccccc1-c1ccc(Cl)cc1>>Clc1ccc2c(c1)[nH]c1ccccc12 | ClC1=CC=C(C=C1)C1=C(C=CC=C1)[N+](=O)[O-].P(OCC)(OCC)OCC>>ClC1=CC=2NC3=CC=CC=C3C2C=C1 | O=[N+:8]([O-])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1-[c:5]1[cH:4][cH:3][c:2]([Cl:1])[cH:7][cH:6]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[nH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]21 | O=[N+]([O-])c1ccccc1-c1ccc(Cl)cc1 | Clc1ccc2c(c1)[nH]c1ccccc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | c5f4769fc5976180f530ad8a69b1753fde9d391f37b7a84ae146448896d5f600 | 899ebca2d6bba86d6be0360dea40833668d6eca1204c0c9fa1f9358f23c9856e | c1ccc2c(c1)[nH]c1ccccc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:5]1:[c:6]:[c:7]:[c:8]:[c:9]:[cH;D2;+0:10]:1):[c:11]:[c:12]>>[c:3]:[c:2]1:[nH;D2;+0:1]:[c;H0;D3;+0:10]2:[c:9]:[c:8]:[c:7]:[c:6]:[c;H0;D3;+0:5]:2:[c;H0;D3;+0:4]:1:[c:11]:[c:12] | 69.2 | [{"value": 69.2, "product": "ClC1=CC=2NC3=CC=CC=C3C2C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | A mixture of 4′-Chloro-2-nitrobiphenyl (640 mg) and triethyl phosphite (1.9 ml) was heated at 150° C. for 3 hrs. The mixture was then allowed to cool and purified by flash chromatography (5–10% ethyl acetate/hexane) to afford the sub-title compound as a white solid (382 mg): 1H NMR (400 MHz, d6-DMSO) δ 7.12–7.23 (2H, m... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | null | c1ccccc1.c1ccccc1 | c1ccc2c(c1)[nH]c1ccccc12 | c1ccc2c(c1)[nH]c1ccccc12 | Other | null | 150 | null | O=[N+]([O-])c1ccccc1-c1ccc(Cl)cc1>>Clc1ccc2c(c1)[nH]c1ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a4077a8ec4144f13941b8af582ce50fa | O=C(Cl)OC(Cl)(Cl)Cl>>NC(=O)Cl | ClC1=CC=2NC3=CC=CC=C3SC2C=C1.O=C(OC(Cl)(Cl)Cl)Cl>>C(N)(=O)Cl.ClC1=CC=2NC3=CC=CC=C3SC2C=C1 | ClC(Cl)(Cl)O[C:17](=[O:18])[Cl:19]>>[NH2:16][C:17](=[O:18])[Cl:19] | O=C(Cl)OC(Cl)(Cl)Cl | NC(=O)Cl | null | null | C=1(C(=CC=CC1)C)C | Miscellaneous | Ester with ammonia to amide | 05045ab1a8125e4d9e5981dd62e6d564464575f2ef96f214ea54e168eca913ff | 83ae9232acbb75071dd354fa93a31e52bf7784c0dbc48352b327235706cd1493 | null | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](-[Cl;D1;H0:2])=[O;D1;H0:3]>>[Cl;D1;H0:2]-[C;H0;D3;+0:1](-[N;D1;H2:4])=[O;D1;H0:3] | 152.2 | [{"value": 152.2, "product": "C(N)(=O)Cl.ClC1=CC=2NC3=CC=CC=C3SC2C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | To a suspension of 2-chlorophenothiazine (2 g) in xylene (20 ml)was added diphosgene (3.4 g). The mixture was heated to 140° C. for 18 hrs. The mixture was then cooled and the xylene removed under reduced pressure. The residue was purified by flash chromatography (2–5% ethyl acetate/hexane) to afford the sub-title comp... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trichloro group.Ether | Acyl halide.Primary amide | null | null | null | Other | C=1(C(=CC=CC1)C)C | 140 | null | O=C(Cl)OC(Cl)(Cl)Cl>C=1(C(=CC=CC1)C)C>NC(=O)Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-215e1a78f78e40ffbc1ff706fef971b2 | N#Cc1ncccc1F.[Cl-].[NH4+]>>Cl.N=C(N)c1ncccc1F | C[O-].[Na+].[Na].C(#N)C1=NC=CC=C1F.[Cl-].[NH4+].C(C)(=O)O>>Cl.C(N)(=N)C1=NC=CC=C1F | [N:2]#[C:3][c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[F:11].[Cl-:1].[NH4+:4]>>[ClH:1].[NH:2]=[C:3]([NH2:4])[c:5]1[n:6][cH:7][cH:8][cH:9][c:10]1[F:11] | N#Cc1ncccc1F.[Cl-].[NH4+] | Cl.N=C(N)c1ncccc1F | null | null | CO | Functional Group Interconversion | OtherReaction | 3b047a13c16a607c445b1c419e256808e8c9a0097d8fb9efd4e7970deb782b70 | 2882e57127fc469aa16ca9a2fd53388b6d97c74c76c010e6eb01be5726f46aa5 | c1ccncc1 | [Cl-;H0;D0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4](:[c:5]):[#7;a:6]:[c:7].[NH4+;D0:8]>>[ClH;D0;+0:1].[NH2;D1;+0:8]-[C;H0;D3;+0:3](=[NH;D1;+0:2])-[c:4](:[c:5]):[#7;a:6]:[c:7] | null | [] | 20 | CELSIUS | 72 | HOUR | A sodium methoxide solution made from 0.40 g (17.391 mmol) of sodium and 65 ml of methanol is added to a solution of 10.30 g (84.355 mmol) of the compound from Example II in 30 ml of methanol, and the mixture is stirred at 20° C. for 72 hours. 5.44 g (101.682 mmol) of ammonium chloride (powdered) and 17.39 mmol (1.04 m... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccncc1 | null | CO | 20 | 72 | N#Cc1ncccc1F.[Cl-].[NH4+]>CO>Cl.N=C(N)c1ncccc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fa415c37887b4ae1b30cfd84fac67006 | COC(=O)CC(C)=O.O=Cc1ccc(F)cc1Cl>>COC(=O)C(=Cc1ccc(F)cc1Cl)C(C)=O | C(C)(=O)O.N1CCCCC1.ClC1=C(C=O)C=CC(=C1)F.C(CC(=O)C)(=O)OC>>C(C)(=O)C(C(=O)OC)=CC1=C(C=C(C=C1)F)Cl | [CH3:1][O:2][C:3](=[O:4])[CH2:5][C:15]([CH3:16])=[O:17].O=[CH:6][c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]1[Cl:14]>>[CH3:1][O:2][C:3](=[O:4])[C:5](=[CH:6][c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]1[Cl:14])[C:15]([CH3:16])=[O:17] | COC(=O)CC(C)=O.O=Cc1ccc(F)cc1Cl | COC(=O)C(=Cc1ccc(F)cc1Cl)C(C)=O | null | null | C(C)(C)O | C-C Coupling | Aldol condensation | 2b064f56d0fb30f3c1f00b34a5283f06be8ba4a3c6226ddd5a2782886d46fcc6 | 9e67bfff0c53bb596af7a9a722d257d29d8c7cdfc3f48dea44b9b07e7d675755 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]>>[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12] | null | [] | null | null | 8 | HOUR | 1.7 ml of piperidine acetate are added to a solution of 50 g (315 mmol) of 2-chloro-4-fluorobenzaldehyde and 36.6 g (315 mmol) of methyl acetoacetate in 150 ml of isopropanol. Stirring at room temperature overnight is followed by dilution with dichloromethane and extraction with water, and the organic phase is dried ov... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone.Ester | null | null | c1ccccc1 | HO- | C(C)(C)O | null | 8 | COC(=O)CC(C)=O.O=Cc1ccc(F)cc1Cl>C(C)(C)O>COC(=O)C(=Cc1ccc(F)cc1Cl)C(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-66697104511a4a11a5a05a459f0b31cc | C1COCCN1.COC(=O)CC(=O)CCl>>COC(=O)CC(=O)CN1CCOCC1 | Cl.N1CCOCC1.ClCC(CC(=O)OC)=O.O>>N1(CCOCC1)CC(CC(=O)OC)=O | [NH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1.Cl[CH2:8][C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])=[O:7]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][C:6](=[O:7])[CH2:8][N:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1 | C1COCCN1.COC(=O)CC(=O)CCl | COC(=O)CC(=O)CN1CCOCC1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 505036e350a62516c632060eeae05d8239108a346b706af40653d2560d91da48 | 98b92c1800516dd6f2e7ad31e751bba9f02d8a8062f38a8945939bbe90ecca84 | C1COCCN1 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7].[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#8:8]-[C:13]-[C:12]-1 | null | [] | null | null | 4 | HOUR | 1.27 g (14.6 mmol) of morpholine are added to a solution of 1.0 g (6.64 mmol) of methyl 4-chloroacetoacetate in 10 ml of dichloromethane, and the mixture is stirred at room temperature for 4 hours. Water is then added and the mixture is neutralized with 2N hydrochloric acid. The organic phase is dried over sodium sulfa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Secondary amine | Ketone.Tertiary amine | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1 | HCl | ClCCl | null | 4 | C1COCCN1.COC(=O)CC(=O)CCl>ClCCl>COC(=O)CC(=O)CN1CCOCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0778915747554df0b33f837117a41077 | C=[N+]1CCSC1.COC(=O)C(=Cc1ccc(F)cc1Cl)C(C)=O>>COC(=O)C(=Cc1ccc(F)cc1Cl)C(=O)CCN1CCSC1 | C(C)(=O)C(C(=O)OC)=CC1=C(C=C(C=C1)F)Cl.[Cl-].C=[N+]1CSCC1>>ClC1=C(C=CC(=C1)F)C=C(C(=O)OC)C(CCN1CSCC1)=O | [CH2:18]=[N+:19]1[CH2:20][CH2:21][S:22][CH2:23]1.[CH3:1][O:2][C:3](=[O:4])[C:5](=[CH:6][c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]1[Cl:14])[C:15](=[O:16])[CH3:17]>>[CH3:1][O:2][C:3](=[O:4])[C:5](=[CH:6][c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]1[Cl:14])[C:15](=[O:16])[CH2:17][CH2:18][N:19]1[CH2:20][CH2:21][S:22][C... | C=[N+]1CCSC1.COC(=O)C(=Cc1ccc(F)cc1Cl)C(C)=O | COC(=O)C(=Cc1ccc(F)cc1Cl)C(=O)CCN1CCSC1 | null | null | C(C)#N | C-C Coupling | OtherReaction | 90033a86d9a3700fc87c4cb395c8f6538bb6a05ecf3d18ae755d55f073d59d54 | a72e6aa22aadb83ea40a91cbdaed3ede7144c65171b305afa9de820466fb88b0 | O=C(C=Cc1ccccc1)CCN1CCSC1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4](=[C:5]-[c:6])-[C:7](-[CH3;D1;+0:8])=[O;D1;H0:9].[CH2;D1;+0:10]=[N+;H0;D3:11]1-[C:12]-[C:13]-[#16:14]-[C:15]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4](=[C:5]-[c:6])-[C:7](=[O;D1;H0:9])-[CH2;D2;+0:8]-[CH2;D2;+0:10]-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[#16:14]-[C:15]-1 | null | [] | null | null | null | null | 3.24 g (12.6 mmol) of methyl 2-acetyl-3-(2-chloro-4-fluorophenyl)acrylate from Example VII are stirred with 1.74 g (12.6 mmol) of 3-methylene-1,3-thiazolidin-3-ium chloride [prepared in analogy to H. Mohrle et al., Z. Naturforsch. 42, 1035–1046 (1987)] in 50 ml of acetonitrile at 40° C. for 48 hours. After concentratio... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone.Tertiary amine | C1CSC[NH+]1 | C1CSC[NH]1 | c1ccccc1.C1CSC[NH]1 | null | C(C)#N | null | null | C=[N+]1CCSC1.COC(=O)C(=Cc1ccc(F)cc1Cl)C(C)=O>C(C)#N>COC(=O)C(=Cc1ccc(F)cc1Cl)C(=O)CCN1CCSC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d29d70ea4abd46d3b4624c631e1e26d1 | COC(=O)CC(=O)CCc1ccncc1.O=Cc1ccc(F)cc1Cl>>COC(=O)C(=Cc1ccc(F)cc1Cl)C(=O)CCc1ccncc1 | ClC1=C(C=O)C=CC(=C1)F.O=C(CC(=O)OC)CCC1=CC=NC=C1.N1CCCCC1.C(C)(=O)O>>ClC1=C(C=CC(=C1)F)C=C(C(=O)OC)C(CCC1=CC=NC=C1)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][C:15](=[O:16])[CH2:17][CH2:18][c:19]1[cH:20][cH:21][n:22][cH:23][cH:24]1.O=[CH:6][c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]1[Cl:14]>>[CH3:1][O:2][C:3](=[O:4])[C:5](=[CH:6][c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]1[Cl:14])[C:15](=[O:16])[CH2:17][CH2:18][c:19]1[cH:20][cH:21][n:22][... | COC(=O)CC(=O)CCc1ccncc1.O=Cc1ccc(F)cc1Cl | COC(=O)C(=Cc1ccc(F)cc1Cl)C(=O)CCc1ccncc1 | null | null | C(C)(C)O | C-C Coupling | Aldol condensation | 2b064f56d0fb30f3c1f00b34a5283f06be8ba4a3c6226ddd5a2782886d46fcc6 | 9e67bfff0c53bb596af7a9a722d257d29d8c7cdfc3f48dea44b9b07e7d675755 | O=C(C=Cc1ccccc1)CCc1ccncc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]>>[C:5]-[C:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12] | null | [] | null | null | 8 | HOUR | A solution of 2.44 g (15.4 mmol) of 2-chloro-4-fluorobenzaldehyde and 3.19 g (15.4 mmol) of the compound from Example X in 20 ml of isopropanol are mixed with 0.1 ml of piperidine and 0.13 ml of glacial acetic acid. Stirring at room temperature overnight is followed by concentration, and the residue is chromatographed ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone.Ester | null | null | c1ccccc1.c1ccncc1 | HO- | C(C)(C)O | null | 8 | COC(=O)CC(=O)CCc1ccncc1.O=Cc1ccc(F)cc1Cl>C(C)(C)O>COC(=O)C(=Cc1ccc(F)cc1Cl)C(=O)CCc1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dce66c4685444307a96de17501db1619 | COC(=O)CC(=O)CN1CCOCC1.N=C(N)c1ncc(F)cc1F.O=Cc1ccc(F)cc1Cl>>COC(=O)C1=C(CN2CCOCC2)NC(c2ncc(F)cc2F)=NC1c1ccc(F)cc1Cl | ClC1=C(C=O)C=CC(=C1)F.Cl.FC=1C(=NC=C(C1)F)C(N)=N.N1(CCOCC1)CC(CC(=O)OC)=O.C(C)(=O)[O-].[Na+]>>ClC1=C(C=CC(=C1)F)C1N=C(NC(=C1C(=O)OC)CN1CCOCC1)C1=NC=C(C=C1F)F | O=[C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:7][N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1.[NH2:14][C:15]([c:16]1[n:17][cH:18][c:19]([F:20])[cH:21][c:22]1[F:23])=[NH:24].O=[CH:25][c:26]1[cH:27][cH:28][c:29]([F:30])[cH:31][c:32]1[Cl:33]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH2:7][N:8]2[CH2:9][CH2:10][O:11][CH2:12][... | COC(=O)CC(=O)CN1CCOCC1.N=C(N)c1ncc(F)cc1F.O=Cc1ccc(F)cc1Cl | COC(=O)C1=C(CN2CCOCC2)NC(c2ncc(F)cc2F)=NC1c1ccc(F)cc1Cl | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 48d772594be48f3442c7bb7d62d12add8eb71f0fd4ce486666dd15fe84236fb4 | 1e00d85e932c07f2663034db4daa261f40e5c0023483a89d81f9cac80bdac4cf | C1=C(CN2CCOCC2)NC(c2ccccn2)=NC1c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[#7:3])-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8].O=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12].[#7;a:13]:[c:14]-[C:15](-[NH2;D1;+0:16])=[NH;D1;+0:17]>>[#7:3]-[C:2]-[C;H0;D3;+0:1]1=[C;H0;D3;+0:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8])-[CH;D3;+0:9](-[c:10](:[c:11]):[c:12])-[N;H0;D2;+0:17]=[C... | null | [] | null | null | null | null | A solution of 0.38 g (2.4 mmol) of 2-chloro-4-fluorobenzaldehyde in 10 ml of isopropanol is heated together with 0.46 g (2.4 mmol) of the compound from Example VI, 0.48 g (2.4 mmol) of the compound from Example VIII and 0.24 g (2.88 mmol) of sodium acetate under reflux for 2 hours. The reaction mixture is concentrated,... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ester.Primary amine | Enamine.Ester | null | C1=CNC=NC1 | C1=CNC=NC1.C1COCC[NH]1.c1ccncc1.c1ccccc1 | HO- | C(C)(C)O | null | null | COC(=O)CC(=O)CN1CCOCC1.N=C(N)c1ncc(F)cc1F.O=Cc1ccc(F)cc1Cl>C(C)(C)O>COC(=O)C1=C(CN2CCOCC2)NC(c2ncc(F)cc2F)=NC1c1ccc(F)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2fba051fc5664ebf804df2ddb251efca | COC(=O)C(=Cc1ccc(F)cc1Cl)C(=O)CCN1CCSC1.N=C(N)c1ncc(F)cc1F>>COC(=O)C1=C(CCN2CCSC2)NC(c2ncc(F)cc2F)=NC1c1ccc(F)cc1Cl | ClC1=C(C=CC(=C1)F)C=C(C(=O)OC)C(CCN1CSCC1)=O.Cl.FC=1C(=NC=C(C1)F)C(N)=N.C(C)(=O)[O-].[Na+]>>ClC1=C(C=CC(=C1)F)C1N=C(NC(=C1C(=O)OC)CCN1CSCC1)C1=NC=C(C=C1F)F | O=[C:6]([C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:25][c:26]1[cH:27][cH:28][c:29]([F:30])[cH:31][c:32]1[Cl:33])[CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][S:12][CH2:13]1.[NH2:14][C:15]([c:16]1[n:17][cH:18][c:19]([F:20])[cH:21][c:22]1[F:23])=[NH:24]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][S:12][CH... | COC(=O)C(=Cc1ccc(F)cc1Cl)C(=O)CCN1CCSC1.N=C(N)c1ncc(F)cc1F | COC(=O)C1=C(CCN2CCSC2)NC(c2ncc(F)cc2F)=NC1c1ccc(F)cc1Cl | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 9ab50850f7ed7b5264a8b4305f17dd4599c86fdc66a5eea2c8cb3ac6f30486cf | 228bcdaccb8d009aee7ac645576878a2e687b55f80a3a59bf7b8c6a649e8887c | C1=C(CCN2CCSC2)NC(c2ccccn2)=NC1c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C;H0;D3;+0:4](=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12].[#7;a:13]:[c:14]-[C:15](-[NH2;D1;+0:16])=[NH;D1;+0:17]>>[#7;a:13]:[c:14]-[C:15]1=[N;H0;D2;+0:17]-[CH;D3;+0:5](-[c:6](:[c:7]):[c:8])-[C;H0;D3;+0:4](-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12])=[C;H0;... | null | [] | null | null | null | null | A solution of 0.20 g (0.56 mmol) of the compound from Example IX in 5 ml of isopropanol is heated together with 0.11 g (0.56 mmol) of the compound from Example VI and 0.06 g (0.67 mmol) of sodium acetate under reflux for 2 hours. The reaction mixture is concentrated, and the residue is taken up in ethyl acetate and ext... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Enamine.Ester | null | C1=CNC=NC1 | C1=CNC=NC1.C1CSC[NH]1.c1ccncc1.c1ccccc1 | HO- | C(C)(C)O | null | null | COC(=O)C(=Cc1ccc(F)cc1Cl)C(=O)CCN1CCSC1.N=C(N)c1ncc(F)cc1F>C(C)(C)O>COC(=O)C1=C(CCN2CCSC2)NC(c2ncc(F)cc2F)=NC1c1ccc(F)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b610980781e74c28a501900471243f2b | C1CCNCC1.COC(=O)C1=C(CBr)NC(c2ncc(F)cc2F)=N[C@H]1c1ccc(F)cc1Cl>>COC(=O)C1=C(CN2CCCCC2)NC(c2ncc(F)cc2F)=N[C@H]1c1ccc(F)cc1Cl | BrCC1=C([C@@H](N=C(N1)C1=NC=C(C=C1F)F)C1=C(C=C(C=C1)F)Cl)C(=O)OC.N1CCCCC1>>ClC1=C(C=CC(=C1)F)[C@@H]1N=C(NC(=C1C(=O)OC)CN1CCCCC1)C1=NC=C(C=C1F)F | [NH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1.Br[CH2:7][C:6]1=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C@H:25]([c:26]2[cH:27][cH:28][c:29]([F:30])[cH:31][c:32]2[Cl:33])[N:24]=[C:15]([c:16]2[n:17][cH:18][c:19]([F:20])[cH:21][c:22]2[F:23])[NH:14]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH2:7][N:8]2[CH2:9][CH2:10][CH2:11][CH2:... | C1CCNCC1.COC(=O)C1=C(CBr)NC(c2ncc(F)cc2F)=N[C@H]1c1ccc(F)cc1Cl | COC(=O)C1=C(CN2CCCCC2)NC(c2ncc(F)cc2F)=N[C@H]1c1ccc(F)cc1Cl | null | null | O.CO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1=C(CN2CCCCC2)NC(c2ccccn2)=N[C@H]1c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]1=[C:3](-[C:4](-[#8:5])=[O;D1;H0:6])-[C:7]-[#7:8]=[C:9]-[#7:10]-1.[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]1=[C:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13](-[C:14]-[C:15])-[C:12]-[C:11])-[#7:10]-[C:9]=[#7:8]-[C:7]-1 | null | [] | null | null | 30 | MINUTE | A solution of 100 mg of freshly prepared methyl (R)-6-bromomethyl-4-(2-chloro-4-fluorophenyl)-2-(3,5-difluoro-2-pyridyl)-1,4-dihydropyrimidine-5-carboxylate from Example XIII in 0.5 ml of methanol is mixed with 5 equivalents of piperidine and stirred at room temperature for 30 minutes. The solution is diluted with wate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1=CNC=NC1.C1CC[NH]CC1.c1ccncc1.c1ccccc1 | HBr | O.CO | null | 0.5 | C1CCNCC1.COC(=O)C1=C(CBr)NC(c2ncc(F)cc2F)=N[C@H]1c1ccc(F)cc1Cl>O.CO>COC(=O)C1=C(CN2CCCCC2)NC(c2ncc(F)cc2F)=N[C@H]1c1ccc(F)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c0bdd281f2a1438cbfdc0ec971cfa863 | CC(C)(C)OC(=O)NCCC1CCCCN1.Fc1ccccn1>>CC(C)(C)OC(=O)NCCC1CCN(c2ccccn2)CC1 | C(C)(C)(C)OC(=O)NCCC1NCCCC1.CCN(C(C)C)C(C)C.FC1=NC=CC=C1>>C(C)(C)(C)OC(=O)NCCC1CCN(CC1)C1=NC=CC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][CH2:22][CH2:21][NH:14]1.F[c:15]1[cH:16][cH:17][cH:18][cH:19][n:20]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][cH:17][cH:18][cH:19][n:20]2)[CH2:21][CH2:2... | CC(C)(C)OC(=O)NCCC1CCCCN1.Fc1ccccn1 | CC(C)(C)OC(=O)NCCC1CCN(c2ccccn2)CC1 | null | null | CC#N | Heteroatom Alkylation and Arylation | OtherReaction | 10c6f9b26f855d26243e4771b69ba961e55fa770e633c60af6779c5e67cf6f43 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCCC2)nc1 | F-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[CH;D3;+0:8]1-[C:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[C:12]-[NH;D2;+0:13]-1>>[C:6]-[C:7]-[CH;D3;+0:8]1-[C:9]-[CH2;D2;+0:10]-[N;H0;D3;+0:13](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5])-[C:12]-[CH2;D2;+0:11]-1 | null | [] | 100 | CELSIUS | null | null | To a solution of N-t-butoxycarbonyl 2-(piperidin-2-yl)ethylamine (8.1 g) and DIEA (14.1 mL) in CH3CN (29 mL) is added 2-fluoropyridine (3.5 mL) and the resulting mixture is heated in a sealed-tube at 100° C. for three days. Solvent is removed and the crude product is purified via column chromatography (20% EtOAc/hexane... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccncc1 | C1CC[NH]CC1.c1ccncc1 | C1CC[NH]CC1.c1ccncc1 | HF | CC#N | 100 | null | CC(C)(C)OC(=O)NCCC1CCCCN1.Fc1ccccn1>CC#N>CC(C)(C)OC(=O)NCCC1CCN(c2ccccn2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-451df465c903453589d5e1a3fac260c1 | CC(C)(C)OC(=O)ONCCc1ccc(O)cc1.CN(C)C(=O)Cl>>CN(C)C(=O)Oc1ccc(CCNOC(=O)OC(C)(C)C)cc1 | CCOC(=O)C.C(C)(C)(C)OC(=O)ONCCC1=CC=C(C=C1)O.CCN(CC)CC.CN(C(=O)Cl)C>>C(C)(C)(C)OC(=O)ONCCC1=CC=C(C=C1)OC(=O)N(C)C | [OH:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][CH2:12][NH:13][O:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[cH:22][cH:23]1.Cl[C:4]([N:2]([CH3:1])[CH3:3])=[O:5]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[O:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][CH2:12][NH:13][O:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[... | CC(C)(C)OC(=O)ONCCc1ccc(O)cc1.CN(C)C(=O)Cl | CN(C)C(=O)Oc1ccc(CCNOC(=O)OC(C)(C)C)cc1 | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Protection | Schotten-Baumann to ester | 76fc23af07d8d02fec539138b5d326dfd4e833212bae1d173120f54983c8b7d8 | 4c7d92b589147a4e2aa8407ff52bd0eb1be84bdb6595779d27beb0c5d6fdd0e2 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 8 | HOUR | N-t-butoxycarbonyloxy 2-(4-hydroxyphenyl)ethylamine (2.53 g, 10.7 mmol), Et3N (2.96 mL, 2 eq.), a catalytic amount of DMAP (131 mg) and dimethylcarbamyl chloride (2.0 mL, 2 eq.) are mixed in CH2Cl2 at 0° C. The resulting mixture is stirred overnight. EtOAc is added to dilute the reaction mixture and then is washed with... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Aromatic alcohol | Carbamic ester | null | null | c1ccccc1 | HCl | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 8 | CC(C)(C)OC(=O)ONCCc1ccc(O)cc1.CN(C)C(=O)Cl>CN(C)C=1C=CN=CC1.C(Cl)Cl>CN(C)C(=O)Oc1ccc(CCNOC(=O)OC(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c05c840d82b94ae5a767d91914f93f0d | CC(C)(C)OC(=O)ONCCC1CCNCC1.Clc1ccncc1>>CC(C)(C)OC(=O)ONCCC1CCN(c2ccncc2)CC1 | C(C)(C)(C)OC(=O)ONCCC1CCNCC1.Cl.ClC1=CC=NC=C1>>C(C)(C)(C)OC(=O)ONCCC1CCN(CC1)C1=CC=NC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[O:8][NH:9][CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][NH:15][CH2:22][CH2:23]1.Cl[c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[O:8][NH:9][CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][N:15]([c:16]2[cH:17][cH:18][n:19][cH:20][cH:21]2)[... | CC(C)(C)OC(=O)ONCCC1CCNCC1.Clc1ccncc1 | CC(C)(C)OC(=O)ONCCC1CCN(c2ccncc2)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 10c6f9b26f855d26243e4771b69ba961e55fa770e633c60af6779c5e67cf6f43 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCCCC2)ccn1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1.[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1)-[C:10]-[C:11] | null | [] | null | null | null | null | N-t-butoxycarbonyloxy 2-(piperidin-4-yl)-ethylamine (prepared as above) (14.4 g, 50 mmol), 4-chloropyridine HCl (1.0 eq., 8.0 g), TEA (2.2 eq.) are mixed in ethanol, and maintained under reflux overnight. The desired compound, N-t-butoxycarbonyloxy 2-[1-(pyrid-4-yl)piperidin-4-yl]-ethylamine, is isolated by column chro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccncc1 | C1CC[NH]CC1.c1ccncc1 | C1CC[NH]CC1.c1ccncc1 | HCl | C(C)O | null | null | CC(C)(C)OC(=O)ONCCC1CCNCC1.Clc1ccncc1>C(C)O>CC(C)(C)OC(=O)ONCCC1CCN(c2ccncc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7720740d4fb445fe92169049cc1dcd51 | COC(=O)C[C@@H](N)C(=O)OC.O=Cc1ccccc1[N+](=O)[O-]>>COC(=O)CC(NCc1ccccc1[N+](=O)[O-])C(=O)OC | C(#N)[BH3-].[Na+].Cl.COC([C@H](N)CC(=O)OC)=O.C(C)(=O)[O-].[Na+].[N+](=O)([O-])C1=C(C=O)C=CC=C1>>COC(C(CC(=O)OC)NCC1=C(C=CC=C1)[N+](=O)[O-])=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][C@@H:6]([NH2:7])[C:18](=[O:19])[O:20][CH3:21].O=[CH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N+:15](=[O:16])[O-:17]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N+:15](=[O:16])[O-:17])[C:18](=[O:19])[O:20][CH3:21] | COC(=O)C[C@@H](N)C(=O)OC.O=Cc1ccccc1[N+](=O)[O-] | COC(=O)CC(NCc1ccccc1[N+](=O)[O-])C(=O)OC | null | null | C(C)O | Functional Group Addition | Reductive amination with aldehyde | d42fc338dbdae89d3c539bd9d12d3b5ac50c40ef3b87bdc4c4d930c8ee74fb7d | b4dd31b60400cab3abb24376ebe2822f4ce30c85b6d3b9ac994d7e3c5f2bfd96 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C@@H;D3;+0:10](-[NH2;D1;+0:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15]>>[C;D1;H3:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9]-[CH;D3;+0:10](-[NH;D2;+0:11]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15] | 99 | [{"value": 99.0, "product": "COC(C(CC(=O)OC)NCC1=C(C=CC=C1)[N+](=O)[O-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A mixture of D-aspartic acid dimethyl ester hydrochloride (4.2 g, 21.25 mmol) and sodium acetate (1.46 g, 17.85 mmol) was stirred in 25 mL of warm ethanol for 10 min. 2-Nitrobenzaldehyde (1.35 g, 8.936 mmol) was added and stirring was continued at room temperature for 1.5 h. Sodium cyanoborohydride (333.88 mg, 5.31 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1 | Other | C(C)O | null | 1.5 | COC(=O)C[C@@H](N)C(=O)OC.O=Cc1ccccc1[N+](=O)[O-]>C(C)O>COC(=O)CC(NCc1ccccc1[N+](=O)[O-])C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-23085d74e8b84ffc85b6cd273237a8e0 | COC(=O)CC(NCc1ccccc1[N+](=O)[O-])C(=O)OC>>COC(=O)CC(NCc1ccccc1N)C(=O)OC | COC(C(CC(=O)OC)NCC1=C(C=CC=C1)[N+](=O)[O-])=O.[H][H]>>COC(C(CC(=O)OC)NCC1=C(C=CC=C1)N)=O | O=[N+:15]([O-])[c:14]1[c:9]([CH2:8][NH:7][CH:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[C:16](=[O:17])[O:18][CH3:19])[cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]([NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[NH2:15])[C:16](=[O:17])[O:18][CH3:19] | COC(=O)CC(NCc1ccccc1[N+](=O)[O-])C(=O)OC | COC(=O)CC(NCc1ccccc1N)C(=O)OC | null | [Pt]=O | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A mixture of 2-(2-nitrobenzylamino)succinic acid dimethyl ester [from a) above] (7.6 g, 25.65 mmol) and platinum oxide (349.51 mg, 1.54 mmol) was shaken in methanol on a Parr hydrogenation apparatus under 50 psi of hydrogen gas. After 12 h the mixture was filtered and concentrated to give 6.6 g of the title compound as... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pt]=O.CO | null | null | COC(=O)CC(NCc1ccccc1[N+](=O)[O-])C(=O)OC>[Pt]=O.CO>COC(=O)CC(NCc1ccccc1N)C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a1c68688fb7b47d79881ac9a39a8a64e | Cc1ccc(C)c(Cl)c1.O=C(Cl)CCl>>Cc1cc(C(Cl)C(=O)c2ccccc2)c(C)cc1Cl | Cl.ClC1=C(C=CC(=C1)C)C.ClCC(=O)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>>ClC(C(=O)C1=CC=CC=C1)C1=C(C=C(C(=C1)C)Cl)C | [CH3:1][c:2]1[cH:3][cH:4][c:15]([CH3:16])[cH:17][c:18]1[Cl:19].Cl[C:7]([CH2:5][Cl:6])=[O:8]>>[CH3:1][c:2]1[cH:3][c:4]([CH:5]([Cl:6])[C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]([CH3:16])[cH:17][c:18]1[Cl:19] | Cc1ccc(C)c(Cl)c1.O=C(Cl)CCl | Cc1cc(C(Cl)C(=O)c2ccccc2)c(C)cc1Cl | null | null | ClCCl | C-C Coupling | OtherReaction | 56a84d07d0bd017de3dd7b9a9ed5a67f65827d0fa3295bee5693be9e4fd963da | ba69b70705cd1fcdb9b36f81083a099386aaa6cee03056e050a9d1c9fa61028c | O=C(Cc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[Cl;D1;H0:4].[C;D1;H3:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[C;D1;H3:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[CH;D3;+0:3](-[Cl;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:11](:[c:12]):[c:13]):[c:9]:[c:10] | 134.3 | [{"value": 134.3, "product": "ClC(C(=O)C1=CC=CC=C1)C1=C(C=C(C(=C1)C)Cl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A mixture of 2-chloro-1,4-dimethyl-benzene (5 g, 35.56 mmol) and chloroacetylchloride (4.0 g, 35.6 mmol) was cooled to 0° C. and treated with aluminum chloride (4.74 g, 35.6 mmol) in small portions. The reaction slurry was diluted with dichloromethane and allowed to warm to room temperature. After 30 min the reaction w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary halide | Secondary halide.Ketone | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | null | ClCCl | 0 | null | Cc1ccc(C)c(Cl)c1.O=C(Cl)CCl>ClCCl>Cc1cc(C(Cl)C(=O)c2ccccc2)c(C)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5c4064311ea74a27a6cc0b7160ecaad2 | CC(=O)N(Cc1ccc([C@@H]2CCCC[C@H]2C(=O)O)cc1)c1ccccn1.NC(=O)[C@@H](N)c1ccccc1>>CC(=O)N(Cc1ccc([C@@H]2CCCC[C@H]2C(=O)N[C@H](C(N)=O)c2ccccc2)cc1)c1ccccn1.N | CCN=C=NCCCN(C)C.Cl.N[C@H](C(=O)N)C1=CC=CC=C1.ON1N=NC2=C1C=CC=C2.C(C)(=O)N(C1=NC=CC=C1)CC1=CC=C(C=C1)[C@H]1[C@@H](CCCC1)C(=O)O>>N.C(C)(=O)N(C1=NC=CC=C1)CC1=CC=C(C=C1)[C@H]1[C@@H](CCCC1)C(=O)N[C@H](C(=O)N)C1=CC=CC=C1 | O[C:16]([C@H:15]1[C@H:10]([c:9]2[cH:8][cH:7][c:6]([CH2:5][N:4]([C:2]([CH3:1])=[O:3])[c:31]3[cH:32][cH:33][cH:34][cH:35][n:36]3)[cH:30][cH:29]2)[CH2:11][CH2:12][CH2:13][CH2:14]1)=[O:17].[NH2:18][C@H:19]([C:20]([NH2:21])=[O:22])[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][C:2](=[O:3])[N:4]([CH2:5][c:6]1[cH:7][cH:... | CC(=O)N(Cc1ccc([C@@H]2CCCC[C@H]2C(=O)O)cc1)c1ccccn1.NC(=O)[C@@H](N)c1ccccc1 | CC(=O)N(Cc1ccc([C@@H]2CCCC[C@H]2C(=O)N[C@H](C(N)=O)c2ccccc2)cc1)c1ccccn1.N | null | null | O.C(C)N(CC)CC.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCc1ccccc1)[C@@H]1CCCC[C@H]1c1ccc(CNc2ccccn2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[N;D1;H2:6]-[C:7](=[O;D1;H0:8])-[C:9](-[NH2;D1;+0:10])-[c:11]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9](-[c:11])-[C:7](-[N;D1;H2:6])=[O;D1;H0:8])-[C:5] | 128.9 | [{"value": 128.9, "product": "C(C)(=O)N(C1=NC=CC=C1)CC1=CC=C(C=C1)[C@H]1[C@@H](CCCC1)C(=O)N[C@H](C(=O)N)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | (1R,2R)-2-(4-{[Acetyl(2-pyridinyl)amino]methyl}phenyl)cyclohexanecarboxylic acid (0.44 g) is suspended in DMF (15 ml), (2S)-2-amino-2-phenylethanamide (0.37 g), triethylamine (0.68 ml), 1-hydroxybenzotriazole (0.18 g) and EDC hydrochloride (0.27 g) are admixed and the mixture is stirred at room temperature for 2 days. ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.C1CCCCC1.c1ccccc1.c1ccncc1 | null | O.C(C)N(CC)CC.CN(C)C=O | null | 48 | CC(=O)N(Cc1ccc([C@@H]2CCCC[C@H]2C(=O)O)cc1)c1ccccn1.NC(=O)[C@@H](N)c1ccccc1>O.C(C)N(CC)CC.CN(C)C=O>CC(=O)N(Cc1ccc([C@@H]2CCCC[C@H]2C(=O)N[C@H](C(N)=O)c2ccccc2)cc1)c1ccccn1.N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ea1ad38d1a944a9783b596f002b9656b | O=C(Cl)Cl.OCCNc1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1>>O=C1OCCN1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | C(=O)(Cl)Cl.ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)NCCO.C(C)N(CC)CC>>ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)N1C(OCC1)=O | Cl[C:2](Cl)=[O:1].[OH:3][CH2:4][CH2:5][NH:6][c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][n:13][c:14]([NH:15][c:16]3[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]3)[n:23]2)[cH:24][cH:25][n:26]1>>[O:1]=[C:2]1[O:3][CH2:4][CH2:5][N:6]1[c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][n:13][c:14]([NH:15][c:16]3[cH:17][cH:18][cH:19][c:20]([... | O=C(Cl)Cl.OCCNc1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | O=C1OCCN1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | null | null | C1(=CC=CC=C1)C.C1CCOC1 | Protection | OtherReaction | 409ae6db623d35a623c85b18f242b280b9f522a0888379bf2a8447d2f6ddaeaf | 09d34234396e4fcb6c9907d2b65f1830d32b6ae1889244c67d7e219c3cd01679 | O=C1OCCN1c1cc(-c2ccnc(Nc3ccccc3)n2)ccn1 | Cl-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[OH;D1;+0:3]-[C:4]-[C:5]-[NH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[O;H0;D2;+0:3]-[C:4]-[C:5]-[N;H0;D3;+0:6]-1-[c:7](:[c:8]):[#7;a:9]:[c:10] | null | [] | null | null | 1 | HOUR | Phosgene in toluene (1.9 ml of a 20% commercial solution, 3.5 mmol) is added within five minutes to a solution of 2-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-ylamino}-ethanol (0.88 g, 2.6 mmol) and triethylamine (1.7 ml, 11.7 mmol) in absolute THF (20 ml) at 50° C. After stirring the resulting suspension f... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary alcohol.Secondary amine | Carbamic ester | null | C1COC[NH]1 | C1COC[NH]1.c1ccncc1.c1cncnc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C.C1CCOC1 | null | 1 | O=C(Cl)Cl.OCCNc1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1>C1(=CC=CC=C1)C.C1CCOC1>O=C1OCCN1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-71b823c546504e85b63e3a1e74f4dfa2 | O=S(=O)(Cl)Cl.OCCNc1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1>>O=S1OCCN1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | S(=O)(=O)(Cl)Cl.ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)NCCO.C(C)N(CC)CC>>ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)N1S(OCC1)=O | O=[S:2](Cl)(Cl)=[O:1].[OH:3][CH2:4][CH2:5][NH:6][c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][n:13][c:14]([NH:15][c:16]3[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]3)[n:23]2)[cH:24][cH:25][n:26]1>>[O:1]=[S:2]1[O:3][CH2:4][CH2:5][N:6]1[c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][n:13][c:14]([NH:15][c:16]3[cH:17][cH:18][cH:19][c:2... | O=S(=O)(Cl)Cl.OCCNc1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | O=S1OCCN1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | null | null | C1CCOC1 | Acylation | OtherReaction | 3d2c53a666fb5a577b1313e56f6be1ee5645334dca79c4f10831a331b18034d8 | b742aca93543b8e281f953dd08553590c1a12f1562393e6d8aed2fc78e477c3c | O=S1OCCN1c1cc(-c2ccnc(Nc3ccccc3)n2)ccn1 | Cl-[S;H0;D4;+0:1](-Cl)(=O)=[O;D1;H0:2].[OH;D1;+0:3]-[C:4]-[C:5]-[NH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:2]=[S;H0;D3;+0:1]1-[O;H0;D2;+0:3]-[C:4]-[C:5]-[N;H0;D3;+0:6]-1-[c:7](:[c:8]):[#7;a:9]:[c:10] | null | [] | null | null | 4 | HOUR | A solution of sulfonyl chloride (0.63 g, 5.3 mmol) in THF (2 ml) is added within 5 minutes to a solution of 2-{4-(2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-ylamino}-ethanol (1.50 g, 4.4 mmol) and triethylamine (3.0 ml, 22 mmol) in absolute THF (20 ml) at +5° C. After stirring the resulting suspension for four ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine.Sulfinate | null | C1COS[NH]1 | C1COS[NH]1.c1ccncc1.c1cncnc1.c1ccccc1 | HCl | C1CCOC1 | null | 4 | O=S(=O)(Cl)Cl.OCCNc1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1>C1CCOC1>O=S1OCCN1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3e32834ca23542119a7a7a66f6b9d3a3 | Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1.O=C1CCCN1>>O=C1CCCN1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)Cl.[H-].[Na+].N1C(CCC1)=O>>ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)N1C(CCC1)=O | Cl[c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][n:13][c:14]([NH:15][c:16]3[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]3)[n:23]2)[cH:24][cH:25][n:26]1.[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][NH:6]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][N:6]1[c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][n:13][c:14]([NH:15][c:16]3[cH:17][cH:18][cH:19][c:20](... | Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1.O=C1CCCN1 | O=C1CCCN1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling | b9cb43b0feb9662c34b4660e88ec6e97dbcb0977de455f4966f2a9886c437142 | e3642f27d4c4bc101b8817e43c6aa5a22f60531030ee51c1c76056fd17c8df37 | O=C1CCCN1c1cc(-c2ccnc(Nc3ccccc3)n2)ccn1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[O;D1;H0:6]=[C:7]1-[C:8]-[C:9]-[C:10]-[N;H0;D3;+0:11]-1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | To a solution of (3-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-pyrimidin-2-yl]-amine (4.8 g, 0.015 mol) in pyrrolidon (20 ml) is added sodium hydride (1.93 g, 0.06 mmol of a 75% dispersion in oil) in several portions. The reaction temperature is slowly raised to +150° C. After 30 minutes the heating bath is removed and ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Tertiary amide | c1ccncc1.C1CCNC1 | C1CC[NH]C1.c1ccncc1 | C1CC[NH]C1.c1ccncc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1.O=C1CCCN1>>O=C1CCCN1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b25ff8a8ae9f4a798eef9fbbb9f0225d | CC1COC(=O)N1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1.COCCl>>COCN(c1cccc(Cl)c1)c1nccc(-c2ccnc(N3C(=O)OCC3C)c2)n1 | CC(C)([O-])C.[K+].ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)N1C(OCC1C)=O.ClCOC>>ClC=1C=C(C=CC1)N(C1=NC=CC(=N1)C1=CC(=NC=C1)N1C(OCC1C)=O)COC | [NH:4]([c:5]1[cH:6][cH:7][cH:8][c:9]([Cl:10])[cH:11]1)[c:12]1[n:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][n:20][c:21]([N:22]3[C:23](=[O:24])[O:25][CH2:26][CH:27]3[CH3:28])[cH:29]2)[n:30]1.Cl[CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][N:4]([c:5]1[cH:6][cH:7][cH:8][c:9]([Cl:10])[cH:11]1)[c:12]1[n:13][cH:14][cH:15][c:16... | CC1COC(=O)N1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1.COCCl | COCN(c1cccc(Cl)c1)c1nccc(-c2ccnc(N3C(=O)OCC3C)c2)n1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f05032bd478f2b29c3c411043d219bb8ead01c2b921229d97b766b64248a775b | ee76bd6f46dec2833a5164047e308d22b0c2f15c69808d0f3c01aa1cb3e372db | O=C1OCCN1c1cc(-c2ccnc(Nc3ccccc3)n2)ccn1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C;D1;H3:3].[c:4]:[c:5](-[NH;D2;+0:6]-[c:7](:[#7;a:8]:[c:9]):[#7;a:10]:[c:11]):[c:12]>>[C;D1;H3:3]-[#8:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[c:7](:[#7;a:8]:[c:9]):[#7;a:10]:[c:11])-[c:5](:[c:4]):[c:12] | null | [] | null | null | 5 | HOUR | Potassium t-butoxide (0.235 g, 2.1 mmol) is added at room temperature to a solution of 3-{4-[2-(3-chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4-methyl-oxazolidin-2-one (0.5 g, 1.3 mmol). After stirring the mixture for 10 minutes chloromethylmethylether (0.17 g, 2.1 mmol) in THF (3 ml) is added. The mixture is sti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Secondary amine | Ether.Tertiary amine | null | null | c1ccccc1.c1cncnc1.c1ccncc1.C1COC[NH]1 | HCl | C1CCOC1 | null | 5 | CC1COC(=O)N1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1.COCCl>C1CCOC1>COCN(c1cccc(Cl)c1)c1nccc(-c2ccnc(N3C(=O)OCC3C)c2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-093ba01bce4f43b0bc7ec98e3643815d | CC1CNC(=O)C1.Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1>>CC1CCC(=O)N1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)Cl.CC(C)(C)[O-].[Na+].CC1CC(NC1)=O>>ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)N1C(CCC1C)=O | [CH3:1][CH:2]1[CH2:3][NH:7][C:5](=[O:6])[CH2:4]1.Cl[c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([Cl:22])[cH:23]3)[n:24]2)[cH:25][cH:26][n:27]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][C:5](=[O:6])[N:7]1[c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][cH... | CC1CNC(=O)C1.Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1 | CC1CCC(=O)N1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.[Fe+2].CC(=O)[O-].CC(=O)[O-].[Pd+2] | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | b9cb43b0feb9662c34b4660e88ec6e97dbcb0977de455f4966f2a9886c437142 | e3642f27d4c4bc101b8817e43c6aa5a22f60531030ee51c1c76056fd17c8df37 | O=C1CCCN1c1cc(-c2ccnc(Nc3ccccc3)n2)ccn1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[CH;D3;+0:7]1-[CH2;D2;+0:8]-[NH;D2;+0:9]-[C:10](=[O;D1;H0:11])-[CH2;D2;+0:12]-1>>[C;D1;H3:6]-[CH;D3;+0:7]1-[CH2;D2;+0:8]-[CH2;D2;+0:12]-[C:10](=[O;D1;H0:11])-[N;H0;D3;+0:9]-1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | 120 | CELSIUS | null | null | In a Schlenk tube (3-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-pyrimidin-2-yl]-amine (0.95 g), NaOtBu (0.29 g), dppf (0.1 g), Pd(OAc)2 (0.01 g) and 4-methylpyrrolidin-2one (0.2 g) are added: Three consecutive cycles of vacuum/argon are applied. Thereafter, 10 ml of degassed dioxane is added and the solution is heated t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Tertiary amide | C1CCNC1.c1ccncc1 | C1CC[NH]C1.c1ccncc1 | C1CC[NH]C1.c1ccncc1.c1cncnc1.c1ccccc1 | HCl | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.[Fe+2].CC(=O)[O-].CC(=O)[O-].[Pd+2].O1CCOCC1 | 120 | null | CC1CNC(=O)C1.Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.[Fe+2].CC(=O)[O-].CC(=O)[O-].[Pd+2].O1CCOCC1>CC1CCC(=O)N1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d2089d2c66814fd7a72fe951028b76be | C[C@@H]1COC(=O)N1.Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1>>CC1COC(=O)N1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)Cl.C[C@H]1NC(OC1)=O.CC(C)(C)[O-].[Na+].CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C(C=CC=C51)P(C6=CC=CC=C6)C7=CC=CC=C7)C>>ClC=1C=C(C=CC1)NC1=NC=CC(=N1)C1=CC(=NC=C1)N1C(OCC1C)=O | [CH3:1][C@@H:2]1[CH2:3][O:4][C:5](=[O:6])[NH:7]1.Cl[c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][cH:19][cH:20][c:21]([Cl:22])[cH:23]3)[n:24]2)[cH:25][cH:26][n:27]1>>[CH3:1][CH:2]1[CH2:3][O:4][C:5](=[O:6])[N:7]1[c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][cH:1... | C[C@@H]1COC(=O)N1.Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1 | CC1COC(=O)N1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1(=CC=CC=C1)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Goldberg coupling | e9c601ac44256b6eca3bfb221d87a779ebbbdc2ae0ebb67158081cb6a72b3e6e | 23f4e0d8af1d86d8b907685b9e69e28ed17e2c9c83b8194f1d8a52eb89f58564 | O=C1OCCN1c1cc(-c2ccnc(Nc3ccccc3)n2)ccn1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[C@@H;D3;+0:7]1-[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[NH;D2;+0:12]-1>>[C;D1;H3:6]-[CH;D3;+0:7]1-[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[N;H0;D3;+0:12]-1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | 120 | CELSIUS | null | null | A solution of Xantphos (0.018 g) and Pd2(dba)3 (0.014 g) in toluene (2 ml) is stirred under argon at room temperature for 20 minutes. Then (3-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-pyrimidin-2-yl]-amine (0.20 g), (R)-4-methyl-oxazolidin-2-one (0.127 g), NaOtBu (0.085 g) and toluene ((2 ml) are added. The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester | Carbamic ester | C1COCN1.c1ccncc1 | C1COC[NH]1.c1ccncc1 | C1COC[NH]1.c1ccncc1.c1cncnc1.c1ccccc1 | HCl | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C.C(C)(=O)OCC | 120 | null | C[C@@H]1COC(=O)N1.Clc1cccc(Nc2nccc(-c3ccnc(Cl)c3)n2)c1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C.C(C)(=O)OCC>CC1COC(=O)N1c1cc(-c2ccnc(Nc3cccc(Cl)c3)n2)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cfcef71d43994b6d9aa998dc04b1073e | CS(=O)c1ccccc1.c1cnc2[nH]ccc2c1>>c1ccc(Sc2c[nH]c3ncccc23)cc1 | C(C)N(CC)CC.FC(C(=O)OC(C(F)(F)F)=O)(F)F.C1(=CC=CC=C1)S(=O)C.N1C=CC2=CC=CN=C12>>C1(=CC=CC=C1)SC1=CNC2=NC=CC=C21 | C[S:5](=O)[c:4]1[cH:3][cH:2][cH:1][cH:16][cH:15]1.[cH:6]1[cH:7][nH:8][c:9]2[n:10][cH:11][cH:12][cH:13][c:14]12>>[cH:1]1[cH:2][cH:3][c:4]([S:5][c:6]2[cH:7][nH:8][c:9]3[n:10][cH:11][cH:12][cH:13][c:14]23)[cH:15][cH:16]1 | CS(=O)c1ccccc1.c1cnc2[nH]ccc2c1 | c1ccc(Sc2c[nH]c3ncccc23)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 06c320520f2d83a7287ab31c12dd62e88d64463c6ac161be5a7bebf2d6746c36 | 0eb0a8cdd12ffc1f7d863bcf1c3c069a35e140723fe4ca7bad40fe7e8e02c5c8 | c1ccc(Sc2c[nH]c3ncccc23)cc1 | C-[S;H0;D3;+0:1](=O)-[c:2](:[c:3]):[c:4].[c:5]:[#7;a:6]:[c:7]1:[#7;a:8]:[c:9]:[cH;D2;+0:10]:[c:11]:1:[c:12]>>[c:5]:[#7;a:6]:[c:7]1:[#7;a:8]:[c:9]:[c;H0;D3;+0:10](-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:11]:1:[c:12] | null | [] | -78 | CELSIUS | 30 | MINUTE | A solution of methyl phenyl sulfoxide (8.33 g, 59.4 mmol) in CH2Cl2 is chilled to −78° C. and treated dropwise with trifluoroacetic anhydride (4.1 mL, 5.3 mmol). After stirring for 30 min at −78° C., a solution of 7-azaindole (5.2 g, 44.0 mmol) in CH2Cl2 is added. After 30 min at −78° C., triethylamine (74 mL, 534 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Sulfoxide | Monosulfide | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | c1ccccc1.c1cnc2[nH]ccc2c1 | HO- | C(Cl)Cl | -78 | 0.5 | CS(=O)c1ccccc1.c1cnc2[nH]ccc2c1>C(Cl)Cl>c1ccc(Sc2c[nH]c3ncccc23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-437b7c64f26c4bc3adeafe32628d8bd2 | O=C([O-])c1ccccc1C(=O)[O-].O=S(=O)(c1ccccc1)c1cn(CCCl)c2ncccc12>>O=C1c2ccccc2C(=O)N1CCn1cc(S(=O)(=O)c2ccccc2)c2cccnc21 | ClCCN1C=C(C=2C1=NC=CC2)S(=O)(=O)C2=CC=CC=C2.C(C=1C(C(=O)[O-])=CC=CC1)(=O)[O-].[K+].[K+].CN(C)C=O>>C1(=CC=CC=C1)S(=O)(=O)C1=CN(C2=NC=CC=C21)CCN2C(C1=CC=CC=C1C2=O)=O | [O-][C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C:9]([O-])=[O:10].Cl[CH2:12][CH2:13][n:14]1[cH:15][c:16]([S:17](=[O:18])(=[O:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[cH:27][cH:28][cH:29][n:30][c:31]12>>[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][CH2:13][n:14]1[cH:1... | O=C([O-])c1ccccc1C(=O)[O-].O=S(=O)(c1ccccc1)c1cn(CCCl)c2ncccc12 | O=C1c2ccccc2C(=O)N1CCn1cc(S(=O)(=O)c2ccccc2)c2cccnc21 | null | null | O | Acylation | OtherReaction | 7109a0b7b31142140647b9aada26dd572effbedc40aa92fa31dc8d9953997543 | 0cc3f093347c0b80c39e6af1a676673d9441ad10581229b2df02da847c41edeb | O=C1c2ccccc2C(=O)N1CCn1cc(S(=O)(=O)c2ccccc2)c2cccnc21 | Cl-[CH2;D2;+0:1]-[C:2]-[#7;a:3].[O-]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8](-[C;H0;D3;+0:9](-[O-])=[O;D1;H0:10]):[c:11]>>[#7;a:3]-[C:2]-[CH2;D2;+0:1]-[#7:12]1-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8](:[c:11])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | 115 | CELSIUS | null | null | A solution of 1-(2-chloroethyl)-3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (3.84 g, 12.0 mmol) in DMF is treated with potassium phthalate (2.78 g, 15.0 mmol, heated at 115° C. for 16 h, cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined extracts are washed with brine, dried ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Substituted dicarboximide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccccc1.c1c[nH]c2ncccc12 | Other | O | 115 | null | O=C([O-])c1ccccc1C(=O)[O-].O=S(=O)(c1ccccc1)c1cn(CCCl)c2ncccc12>O>O=C1c2ccccc2C(=O)N1CCn1cc(S(=O)(=O)c2ccccc2)c2cccnc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-da1f783574de4c4192cd16468930a79e | ClCCl.O=C1c2ccccc2C(=O)N1CCn1cc(S(=O)(=O)c2ccccc2)c2cccnc21>>Cl.Cl.NCCn1cc(S(=O)(=O)c2ccccc2)c2cccnc21 | CO.C(Cl)Cl.C1(=CC=CC=C1)S(=O)(=O)C1=CN(C2=NC=CC=C21)CCN2C(C1=CC=CC=C1C2=O)=O.NN>>Cl.Cl.C1(=CC=CC=C1)S(=O)(=O)C1=CN(C2=NC=CC=C21)CCN | C([Cl:1])[Cl:2].O=C1c2ccccc2C(=O)[N:3]1[CH2:4][CH2:5][n:6]1[cH:7][c:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][n:22][c:23]12>>[ClH:1].[ClH:2].[NH2:3][CH2:4][CH2:5][n:6]1[cH:7][c:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][c... | ClCCl.O=C1c2ccccc2C(=O)N1CCn1cc(S(=O)(=O)c2ccccc2)c2cccnc21 | Cl.Cl.NCCn1cc(S(=O)(=O)c2ccccc2)c2cccnc21 | null | null | O1CCOCC1 | Miscellaneous | OtherReaction | b8e4253610d94953fc77d3656ad6916804db671c9799a208ba841862f10f631f | 4000bec491e6d5330b39405fcb2a0e221de2733c50afddf05930d05b326bf486 | O=S(=O)(c1ccccc1)c1c[nH]c2ncccc12 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3])-C(=O)-c2:c:c:c:c:c:2-1.[Cl;H0;D1;+0:4]-C-[Cl;H0;D1;+0:5]>>[C:3]-[C:2]-[NH2;D1;+0:1].[ClH;D0;+0:4].[ClH;D0;+0:5] | null | [] | 50 | CELSIUS | null | null | A solution of 2-{2-[3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-1-yl]ethyl}-1H-isoindole-1,3(2H)-dione (4.54 g, 10.5 mmol) in dioxane is treated with anhydrous hydrazine (8.3 mL, 265 mmol), heated at 50° C. for 3 h, concentrated in vacuo, diluted with water and extracted with CH2Cl2. The combined extracts are dried ove... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccccc1.c1c[nH]c2ncccc12 | HO- | O1CCOCC1 | 50 | null | ClCCl.O=C1c2ccccc2C(=O)N1CCn1cc(S(=O)(=O)c2ccccc2)c2cccnc21>O1CCOCC1>Cl.Cl.NCCn1cc(S(=O)(=O)c2ccccc2)c2cccnc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-02a1f083d3dc4686835dfcf7f1f1edb4 | CN(C)CCCl.O=S(=O)(c1ccccc1)c1c[nH]c2ncccc12>>CN(C)CCn1cc(S(=O)(=O)c2ccccc2)c2cccnc21.Cl | Cl.CN(CCCl)C.C1(=CC=CC=C1)S(=O)(=O)C1=CNC2=NC=CC=C21.[H-].[Na+]>>Cl.Cl.CN(CCN1C=C(C=2C1=NC=CC2)S(=O)(=O)C2=CC=CC=C2)C | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][Cl:25].[nH:6]1[cH:7][c:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][n:22][c:23]12>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][n:6]1[cH:7][c:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21... | CN(C)CCCl.O=S(=O)(c1ccccc1)c1c[nH]c2ncccc12 | CN(C)CCn1cc(S(=O)(=O)c2ccccc2)c2cccnc21.Cl | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 922dacf004d1919466c600e7d5478103889d64a4206d84075556a0260e407480 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=S(=O)(c1ccccc1)c1c[nH]c2ncccc12 | [#7:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[c:5]:[#7;a:6]:[c:7]1:[c:8]:[c:9]:[c:10]:[nH;D2;+0:11]:1>>[#7:1]-[C:2]-[CH2;D2;+0:3]-[n;H0;D3;+0:11]1:[c:10]:[c:9]:[c:8]:[c:7]:1:[#7;a:6]:[c:5].[ClH;D0;+0:4] | null | [] | 20 | CELSIUS | 3 | HOUR | A solution of 3-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (400 mg, 1.55 mmol) in dry DMF is chilled to 0° C., treated with sodium hydride (60% in oil, 97 mg, 2.43 mmol), stirred for 3 h at 20° C., cooled to −20° C., treated with 2-(dimethylamino)-ethyl chloride hydrochloride (336 mg, 2.33 mmol), stirred at 60° C. for ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnc2[nH]ccc2c1 | c1c[nH]c2ncccc12 | c1ccccc1.c1c[nH]c2ncccc12 | null | CN(C)C=O | 20 | 3 | CN(C)CCCl.O=S(=O)(c1ccccc1)c1c[nH]c2ncccc12>CN(C)C=O>CN(C)CCn1cc(S(=O)(=O)c2ccccc2)c2cccnc21.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-42df3d1f981f4040b278629780e78ee9 | II.c1cnc2[nH]ccc2c1>>Ic1c[nH]c2ncccc12 | N1C=CC2=CC=CN=C12.II.[I-].[K+].[OH-].[Na+]>>IC1=CNC2=NC=CC=C21 | I[I:1].[cH:2]1[cH:3][nH:4][c:5]2[n:6][cH:7][cH:8][cH:9][c:10]12>>[I:1][c:2]1[cH:3][nH:4][c:5]2[n:6][cH:7][cH:8][cH:9][c:10]12 | II.c1cnc2[nH]ccc2c1 | Ic1c[nH]c2ncccc12 | null | null | O.C(C)O | Functional Group Interconversion | OtherReaction | 397b1126cd4b423fd3adc318bdfd38847a6f87199ac2b8b69b189481f2f11ff5 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cnc2[nH]ccc2c1 | I-[I;H0;D1;+0:1].[c:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[cH;D2;+0:7]:[c:8]:1:[c:9]>>[I;H0;D1;+0:1]-[c;H0;D3;+0:7]1:[c:6]:[#7;a:5]:[c:4](:[#7;a:3]:[c:2]):[c:8]:1:[c:9] | null | [] | 20 | CELSIUS | 4 | HOUR | A solution of 7-azaindole (20.0 g, 169 mmol) in ethanol is treated with iodine (57.9 g, 228 mmol), potassium iodide (37.8 g, 228 mmol), and 1N aqueous NaOH (204 mL, 204 mmol). After stirring for 4 h at 20° C., the reaction is diluted with water and extracted with ethyl acetate. The organic extracts are combined and con... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | HI | O.C(C)O | 20 | 4 | II.c1cnc2[nH]ccc2c1>O.C(C)O>Ic1c[nH]c2ncccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2b16599a9bcf4da0a76f5b9fbcff1783 | Fc1ccc(S)cc1.Ic1c[nH]c2ncccc12>>Fc1ccc(Sc2c[nH]c3ncccc23)cc1 | IC1=CNC2=NC=CC=C21.FC1=CC=C(C=C1)S.C([O-])([O-])=O.[K+].[K+]>>FC1=CC=C(C=C1)SC1=CNC2=NC=CC=C21 | [F:1][c:2]1[cH:3][cH:4][c:5]([SH:6])[cH:16][cH:17]1.I[c:7]1[cH:8][nH:9][c:10]2[n:11][cH:12][cH:13][cH:14][c:15]12>>[F:1][c:2]1[cH:3][cH:4][c:5]([S:6][c:7]2[cH:8][nH:9][c:10]3[n:11][cH:12][cH:13][cH:14][c:15]23)[cH:16][cH:17]1 | Fc1ccc(S)cc1.Ic1c[nH]c2ncccc12 | Fc1ccc(Sc2c[nH]c3ncccc23)cc1 | null | [Cu](I)I | [NH4+].[OH-].CN(C)C=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution thiol | 85bf550d7a0bf07ee0141a0afecdd4d0d829b6ba6af3885132af75716f253a35 | 97e4acce9b485bd597e518526ab4e9623782b1c9043b6e30dd257d386e3e5b01 | c1ccc(Sc2c[nH]c3ncccc23)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4](:[#7;a:5]:[c:6]):[c:7]:1:[c:8].[SH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:6]:[#7;a:5]:[c:4]1:[#7;a:3]:[c:2]:[c;H0;D3;+0:1](-[S;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:7]:1:[c:8] | null | [] | 65 | CELSIUS | null | null | A solution of 3-iodo-1H-pyrrolo[2,3-b]pyridine (4.0 g, 16.4 mmol) in DMF is treated with 4-fluorobenzenethiol (2.09 mL, 19.7 mmol), potassium carbonate (3.40 g, 24.6 mmol), and copper iodide (4.21 g, 22.1 mmol). The reaction mixture is heated at 65° C. for 4 h, cooled, diluted with conc. aqueous NH4OH and extracted wit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic thiol | Monosulfide | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | c1ccccc1.c1cnc2[nH]ccc2c1 | HI | [Cu](I)I.[NH4+].[OH-].CN(C)C=O | 65 | null | Fc1ccc(S)cc1.Ic1c[nH]c2ncccc12>[Cu](I)I.[NH4+].[OH-].CN(C)C=O>Fc1ccc(Sc2c[nH]c3ncccc23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e23501d3e68a45eaad22311e408f649d | Fc1ccc(Sc2c[nH]c3ncccc23)cc1>>O=S(=O)(c1ccc(F)cc1)c1c[nH]c2ncccc12 | O.FC1=CC=C(C=C1)SC1=CNC2=NC=CC=C21.C(=O)(O)[O-].[Na+].O.OOS(=O)[O-].[K+]>>FC1=CC=C(C=C1)S(=O)(=O)C1=CNC2=NC=CC=C21 | [S:2]([c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[c:11]1[cH:12][nH:13][c:14]2[n:15][cH:16][cH:17][cH:18][c:19]12>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[c:11]1[cH:12][nH:13][c:14]2[n:15][cH:16][cH:17][cH:18][c:19]12 | Fc1ccc(Sc2c[nH]c3ncccc23)cc1 | O=S(=O)(c1ccc(F)cc1)c1c[nH]c2ncccc12 | null | null | CC(=O)C | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | O=S(=O)(c1ccccc1)c1c[nH]c2ncccc12 | [#7;a:1]:[c:2]1:[#7;a:3]:[c:4]:[c:5](-[S;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:10]:1>>[#7;a:1]:[c:2]1:[#7;a:3]:[c:4]:[c:5](-[S;H0;D4;+0:6](=[O;D1;H0:11])(=[O;D1;H0:12])-[c:7](:[c:8]):[c:9]):[c:10]:1 | null | [] | 20 | CELSIUS | 3 | HOUR | A solution of 3-[(4-fluorophenyl)thio]-1H-pyrrolo[2,3-b]pyridine (3.36 g, 13.8 mmol) in acetone is treated with a solution of NaHCO3 (2.90 g, 34.5 mmol) in water. The reaction is then treated with Oxone®1 (25.5 g, 41.4 mmol), stirred for 3 h at 20° C., diluted with water, cooled in an ice-water bath and filtered. The f... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1ccccc1.c1cnc2[nH]ccc2c1 | null | CC(=O)C | 20 | 3 | Fc1ccc(Sc2c[nH]c3ncccc23)cc1>CC(=O)C>O=S(=O)(c1ccc(F)cc1)c1c[nH]c2ncccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3364eb7fc144564b9cf7fd10114c659 | CN(C)CCCl.c1cnc2[nH]ccc2c1>>CN(C)CCn1ccc2cccnc21 | Cl.CN(CCCl)C.N1C=CC=2C1=NC=CC2.[H-].[Na+]>>CN(CCN1C=CC=2C1=NC=CC2)C | Cl[CH2:5][CH2:4][N:2]([CH3:1])[CH3:3].[nH:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][n:13][c:14]12>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][n:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][n:13][c:14]12 | CN(C)CCCl.c1cnc2[nH]ccc2c1 | CN(C)CCn1ccc2cccnc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 4a7f8f8b692ae2793badbdd1eea3a57bb8a1e51ed2fadb9f79ada1bda3f5e10a | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1cnc2[nH]ccc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[c:4]:[#7;a:5]:[c:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]:[c:6]:1:[#7;a:5]:[c:4] | 81 | [{"value": 81.0, "product": "CN(CCN1C=CC=2C1=NC=CC2)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A stirred solution of 1H-pyrrolo[2,3-b]pyridine (5.00 g, 42.3 mmol) in DMF at ambient temperature is treated with 95% sodium hydride in oil (3.78 g, 150 mmol). After gas evolution subsides, the reaction mixture is treated with 2-(dimethylamino)-ethyl chloride hydrochloride (6.40 g, 44.4 mmol), stirred for 16 h and conc... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | HCl | CN(C)C=O | null | 16 | CN(C)CCCl.c1cnc2[nH]ccc2c1>CN(C)C=O>CN(C)CCn1ccc2cccnc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-950e7e4cc06c48058a7258ddcd49622c | CC(Cl)OC(=O)Cl.CN(C)CCn1cc(S(=O)(=O)c2cccc(Cl)c2)c2cccnc21>>CNCCn1cc(S(=O)(=O)c2cccc(Cl)c2)c2cccnc21.Cl | ClC=1C=C(C=CC1)S(=O)(=O)C1=CN(C2=NC=CC=C21)CCN(C)C.ClC(=O)OC(C)Cl>>Cl.ClC=1C=C(C=CC1)S(=O)(=O)C1=CN(C2=NC=CC=C21)CCNC | CC(Cl)OC(=O)[Cl:24].C[N:2]([CH3:1])[CH2:3][CH2:4][n:5]1[cH:6][c:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]2)[c:18]2[cH:19][cH:20][cH:21][n:22][c:23]12>>[CH3:1][NH:2][CH2:3][CH2:4][n:5]1[cH:6][c:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][c:15]([Cl:16])[cH:17]2)[c:18]2[cH:19][c... | CC(Cl)OC(=O)Cl.CN(C)CCn1cc(S(=O)(=O)c2cccc(Cl)c2)c2cccnc21 | CNCCn1cc(S(=O)(=O)c2cccc(Cl)c2)c2cccnc21.Cl | null | null | ClCCCl | Miscellaneous | OtherReaction | 30528ffe0bec50529e03a9f155e678b6c8bb2b443b73569f6233d693c34db80a | 8680972761abf0bd12e62e23250487041204d99e9f76a29275e470fb95a71c86 | O=S(=O)(c1ccccc1)c1c[nH]c2ncccc12 | C-C(-Cl)-O-C(=O)-[Cl;H0;D1;+0:1].C-[N;H0;D3;+0:2](-[C;D1;H3:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[NH;D2;+0:2]-[C;D1;H3:3].[ClH;D0;+0:1] | 108.1 | [{"value": 60.0, "product": "Cl.ClC=1C=C(C=CC1)S(=O)(=O)C1=CN(C2=NC=CC=C21)CCNC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 108.1, "product": "Cl.ClC=1C=C(C=CC1)S(=O)(=O)C1=CN(C2=NC=CC=C21)CCNC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution under nitrogen of N-(2-{3-[(3-chlorophenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-1-yl}ethyl)-N,N-dimethylamine (0.540 g, 1.49 mmol) in 1,2-dichloroethane is treated with 1-chloroethyl chloroformate (0.40 mL, 3.7 mmol), heated at reflux temperature for 2 h cooled, and concentrated in vacuo. The resultant... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary halide.Ether.Tertiary amine | Secondary amine | null | null | c1ccccc1.c1c[nH]c2ncccc12 | HCl | ClCCCl | null | null | CC(Cl)OC(=O)Cl.CN(C)CCn1cc(S(=O)(=O)c2cccc(Cl)c2)c2cccnc21>ClCCCl>CNCCn1cc(S(=O)(=O)c2cccc(Cl)c2)c2cccnc21.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2a0c127228ab49ed83a2eb76d54c03ad | O=S(=O)(CCl)c1ccccc1.O=[N+]([O-])c1cc[n+]([O-])cc1>>O=[N+]([O-])c1cc[n+]([O-])cc1CS(=O)(=O)c1ccccc1 | [N+](=O)([O-])C1=CC=[N+](C=C1)[O-].ClCS(=O)(=O)C1=CC=CC=C1.Cl.[OH-].[K+]>>[N+](=O)([O-])C1=C(C=[N+](C=C1)[O-])CS(=O)(=O)C1=CC=CC=C1 | Cl[CH2:11][S:12](=[O:13])(=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][n+:7]([O-:8])[cH:9][cH:10]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][n+:7]([O-:8])[cH:9][c:10]1[CH2:11][S:12](=[O:13])(=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | O=S(=O)(CCl)c1ccccc1.O=[N+]([O-])c1cc[n+]([O-])cc1 | O=[N+]([O-])c1cc[n+]([O-])cc1CS(=O)(=O)c1ccccc1 | null | null | O.CS(=O)C | C-C Coupling | Friedel-Crafts alkylation with halide | beff72e2d1a9693b2842e7b3718f4795618b202db1e841737f807b1d01f525b8 | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | O=S(=O)(Cc1ccc[nH+]c1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5].[#7;+:6]-[c:7]1:[c:8]:[c:9]:[#7;a;+:10](-[O;-;D1;H0:11]):[c:12]:[cH;D2;+0:13]:1>>[#7;+:6]-[c:7]1:[c:8]:[c:9]:[#7;a;+:10](-[O;-;D1;H0:11]):[c:12]:[c;H0;D3;+0:13]:1-[CH2;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 41 | [{"value": 41.0, "product": "[N+](=O)([O-])C1=C(C=[N+](C=C1)[O-])CS(=O)(=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | Adapting the procedure of Makosza, et al, Liebigs Ann. Chem., 1984, 8–14, a stirred mixture of 4-nitro-pyridine-N-oxide (1.40 g, 10.0 mmol) and chloromethylphenylsulfone (1.92 g, 10.0 mmol) in DMSO (25 mL) in a cold water bath is treated with a solution of KOH (4.0 g, 71 mmol) in DMSO, stirred for 45 min, poured into 1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1.c1ccccc1 | HCl | O.CS(=O)C | null | 0.75 | O=S(=O)(CCl)c1ccccc1.O=[N+]([O-])c1cc[n+]([O-])cc1>O.CS(=O)C>O=[N+]([O-])c1cc[n+]([O-])cc1CS(=O)(=O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-00045ded613241848956e0cb1ebad899 | COc1ccc([N+](=O)[O-])cn1.O=S(=O)(CCl)c1ccccc1>>COc1ccc([N+](=O)[O-])c(CS(=O)(=O)c2ccccc2)n1 | C(C)(=O)O.COC1=NC=C(C=C1)[N+](=O)[O-].CC(C)(C)[O-].[K+].C1(=CC=CC=C1)S(=O)(=O)CCl>>COC1=CC=C(C(=N1)CS(=O)(=O)C1=CC=CC=C1)[N+](=O)[O-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][n:21]1.Cl[CH2:11][S:12](=[O:13])(=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[c:10]([CH2:11][S:12](=[O:13])(=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n:21]1 | COc1ccc([N+](=O)[O-])cn1.O=S(=O)(CCl)c1ccccc1 | COc1ccc([N+](=O)[O-])c(CS(=O)(=O)c2ccccc2)n1 | null | null | O1CCCC1 | C-C Coupling | Friedel-Crafts alkylation with halide | c918ab2b340de388cade9a755e451a5b4caeb6b1c32b83fb98e425e917520b3b | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | O=S(=O)(Cc1ccccn1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5].[#7;+:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[#7;a:10]:[c:11]>>[#7;+:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](-[CH2;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]):[#7;a:10]:[c:11] | 80 | [{"value": 80.0, "product": "COC1=CC=C(C(=N1)CS(=O)(=O)C1=CC=CC=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A 1M KOt-Bu solution in tetrahydrofuran (50 mL, 50 mmol) is cooled to −40° C., treated portion-wise with a solution of chloromethyl phenyl sulfone (4.39 g, 23.0 mmol) and then with a solution of 2-methoxy-5-nitropyridine (3.55 g, 23.0 mmol) in tetrahydrofuran, stirred for 45 min at −40° C., treated with glacial acetic ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | O1CCCC1 | null | null | COc1ccc([N+](=O)[O-])cn1.O=S(=O)(CCl)c1ccccc1>O1CCCC1>COc1ccc([N+](=O)[O-])c(CS(=O)(=O)c2ccccc2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0eb85c8880e1422abb387eb3d19ab874 | COc1ccc([N+](=O)[O-])c(CS(=O)(=O)c2ccccc2)n1>>COc1ccc(N)c(CS(=O)(=O)c2ccccc2)n1 | COC1=CC=C(C(=N1)CS(=O)(=O)C1=CC=CC=C1)[N+](=O)[O-].[Sn]>>NC=1C(=NC(=CC1)OC)CS(=O)(=O)C1=CC=CC=C1 | O=[N+:7]([O-])[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[n:19][c:8]1[CH2:9][S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[c:8]([CH2:9][S:10](=[O:11])(=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[n:19]1 | COc1ccc([N+](=O)[O-])c(CS(=O)(=O)c2ccccc2)n1 | COc1ccc(N)c(CS(=O)(=O)c2ccccc2)n1 | null | null | Cl.CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=S(=O)(Cc1ccccn1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[C:5]):[#7;a:6]:[c:7]>>[C:5]-[c:4](:[#7;a:6]:[c:7]):[c:2](-[NH2;D1;+0:1]):[c:3] | 94.5 | [{"value": 94.0, "product": "NC=1C(=NC(=CC1)OC)CS(=O)(=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.5, "product": "NC=1C(=NC(=CC1)OC)CS(=O)(=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 0.5 | HOUR | A stirred mixture of 6-methoxy-3-nitro-2-[(phenylsulfonyl)methyl]-pyridine (6.17 g, 20.0 mmol) in methanol and concentrated HCl (50 mL) is treated with thin strips of tin foil (10.0 g, 84.2 mmol), heated at 60° C. for 20 h, and filtered hot. The filtrate is poured over ice and 2.5N aqueous NaOH, stirred for 0.5 h and f... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccncc1.c1ccccc1 | Other | Cl.CO | 60 | 0.5 | COc1ccc([N+](=O)[O-])c(CS(=O)(=O)c2ccccc2)n1>Cl.CO>COc1ccc(N)c(CS(=O)(=O)c2ccccc2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4b10d66a37984dbc96ffa4e97a84c346 | CC1CCOC1=O.Clc1ccc(Br)c(Cl)c1>>CC(CCO)C(=O)c1ccc(Cl)cc1Cl | CC1C(=O)OCC1.ClC1=C(C=CC(=C1)Cl)Br.[Li]C(C)(C)C>>ClC1=C(C=CC(=C1)Cl)C(C(CCO)C)=O | [CH3:1][CH:2]1[CH2:3][CH2:4][O:5][C:6]1=[O:7].Br[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]1[Cl:15]>>[CH3:1][CH:2]([CH2:3][CH2:4][OH:5])[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]1[Cl:15] | CC1CCOC1=O.Clc1ccc(Br)c(Cl)c1 | CC(CCO)C(=O)c1ccc(Cl)cc1Cl | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 9b75c16b7b70513642dc717f02a37b46f62ec57b29b424807f67b50b4d55046b | ff736a8b8f5b9a2eccf12416f132f10f74245ffab7958d80d9a24a1730f9912c | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6].[C;D1;H3:7]-[C:8]1-[C:9]-[C:10]-[O;H0;D2;+0:11]-[C;H0;D3;+0:12]-1=[O;D1;H0:13]>>[C;D1;H3:7]-[C:8](-[C:9]-[C:10]-[OH;D1;+0:11])-[C;H0;D3;+0:12](=[O;D1;H0:13])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Cl;D1;H0:5]):[c:6] | 112.6 | [{"value": 112.6, "product": "ClC1=C(C=CC(=C1)Cl)C(C(CCO)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -95 | CELSIUS | 1 | HOUR | To a 2 L, 3-neck round bottom flask, equipped with a mechanic stirrer and an internal temperature controller, is added a solution of 2,4-dichlorobromobenzene (65.5 g, 290.7 mmol) in 1.1 L of THF under nitrogen. The solution is cooled to −95° C. with a MeOH/liquid nitrogen bath. To this solution is added t-BuLi (400 mL,... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Ketone.Primary alcohol | C1CCOC1.c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | C1CCOC1 | -95 | 1 | CC1CCOC1=O.Clc1ccc(Br)c(Cl)c1>C1CCOC1>CC(CCO)C(=O)c1ccc(Cl)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a48105930d4e48379b8a71afc60b946d | Cc1ccn(N2C(=O)c3ccccc3C2=O)c1-c1ccc(Cl)cc1Cl>>Cc1ccn(N)c1-c1ccc(Cl)cc1Cl | ClC1=C(C=CC(=C1)Cl)C=1N(C=CC1C)N1C(C2=CC=CC=C2C1=O)=O.O.NN>>ClC1=C(C=CC(=C1)Cl)C=1N(C=CC1C)N | O=C1c2ccccc2C(=O)[N:6]1[n:5]1[cH:4][cH:3][c:2]([CH3:1])[c:7]1-[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]1[Cl:15]>>[CH3:1][c:2]1[cH:3][cH:4][n:5]([NH2:6])[c:7]1-[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]1[Cl:15] | Cc1ccn(N2C(=O)c3ccccc3C2=O)c1-c1ccc(Cl)cc1Cl | Cc1ccn(N)c1-c1ccc(Cl)cc1Cl | null | null | CCO | Reduction | Phthalimide deprotection | 8c6c904eae7a7d528fa3eeedb7e9706448ab9f7df249a16fa865a9210a6adc85 | 892f9aeb7d80035b81a0f5a363c9ed6a90780ba9faa3f0708093fa283b8c9a24 | c1ccc(-c2ccc[nH]2)cc1 | O=C1-[N;H0;D3;+0:1](-[#7;a:2](:[c:3]):[c:4])-C(=O)-c2:c:c:c:c:c:2-1>>[NH2;D1;+0:1]-[#7;a:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a suspension of 2-[2-(2,4-dichlorophenyl)-3-methyl-1H-pyrrol-1-yl]-1H-isoindole-1,3(2H)-dione (3.71 g, 10.0 mmol) in EtOH (60.0 mL) is added hydrazine monohydrate (1.21 mL, 1.25 g, 25.0 mmol) at room temperature. The reaction mixture is heated at reflux for 2 h. After cooling down to room temperature, the mixture is... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1c[nH]cc1.c1ccccc1 | HO- | CCO | null | null | Cc1ccn(N2C(=O)c3ccccc3C2=O)c1-c1ccc(Cl)cc1Cl>CCO>Cc1ccn(N)c1-c1ccc(Cl)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f7540c29e2da4641995f0337818a3512 | CCOC(=O)/C=C(\C)OCC.Cc1ccn(N)c1-c1ccc(Cl)cc1Cl>>Cc1cc(O)c2cc(C)c(-c3ccc(Cl)cc3Cl)n2n1 | ClC1=C(C=CC(=C1)Cl)C=1N(C=CC1C)N.CCO/C(=C/C(=O)OCC)/C.C1(=CC=C(C=C1)S(=O)(=O)O)C>>ClC1=C(C=CC(=C1)Cl)C1=C(C=C2N1N=C(C=C2O)C)C | CCO/[C:2]([CH3:1])=[CH:3]/[C:4](OCC)=[O:5].[cH:6]1[cH:7][c:8]([CH3:9])[c:10](-[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[Cl:18])[n:19]1[NH2:20]>>[CH3:1][c:2]1[cH:3][c:4]([OH:5])[c:6]2[cH:7][c:8]([CH3:9])[c:10](-[c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]3[Cl:18])[n:19]2[n:20]1 | CCOC(=O)/C=C(\C)OCC.Cc1ccn(N)c1-c1ccc(Cl)cc1Cl | Cc1cc(O)c2cc(C)c(-c3ccc(Cl)cc3Cl)n2n1 | null | null | C(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | ee87b9cf540b79ea0c07617911c58b8a910e02da54d3591517ff27f07783feeb | c469b8a29859a9bb21f9f5379c07196f2b788ee30d8cf0c7f514636339cef44a | c1ccc(-c2ccc3cccnn23)cc1 | C-C-O/[C;H0;D3;+0:1](-[C;D1;H3:2])=[CH;D2;+0:3]/[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-O-C-C.[NH2;D1;+0:6]-[#7;a:7]1:[c:8]:[c:9]:[c:10]:[cH;D2;+0:11]:1>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[OH;D1;+0:5]):[c;H0;D3;+0:11]2:[c:10]:[c:9]:[c:8]:[#7;a:7]:2:[n;H0;D2;+0:6]:1 | null | [] | null | null | null | null | A mixture of 2-(2,4-dichlorophenyl)-3-methyl-1H-pyrrol-1-amine (2.34 g, 9.69 mmol), ethyl trans-3-ethoxycrotonate (1.58 g, 10.0 mmol) and p-toluenesulfonic acid (0.095 g, 0.50 mmol) in CHCl3 (100 mL) is refluxed with a Dean-Stark tube charged with molecular sieves for 24 h. After cooling down to room temperature, the m... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Primary amine | Aromatic alcohol | c1c[nH]cc1 | c1cnn2cccc2c1 | c1cnn2cccc2c1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | null | CCOC(=O)/C=C(\C)OCC.Cc1ccn(N)c1-c1ccc(Cl)cc1Cl>C(Cl)(Cl)Cl>Cc1cc(O)c2cc(C)c(-c3ccc(Cl)cc3Cl)n2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fe61709e1c724f8eba07bdae7be41dea | BrP(Br)Br.Cc1cc(O)c2cc(C)c(-c3ccc(Cl)cc3Cl)n2n1>>Cc1cc(Br)c2cc(C)c(-c3ccc(Cl)cc3Cl)n2n1 | ClC1=C(C=CC(=C1)Cl)C1=C(C=C2N1N=C(C=C2O)C)C.P(Br)(Br)Br.C(=O)(O)[O-].[Na+]>>BrC=1C=2N(N=C(C1)C)C(=C(C2)C)C2=C(C=C(C=C2)Cl)Cl | BrP(Br)[Br:5].O[c:4]1[cH:3][c:2]([CH3:1])[n:20][n:19]2[c:6]1[cH:7][c:8]([CH3:9])[c:10]2-[c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]1[Cl:18]>>[CH3:1][c:2]1[cH:3][c:4]([Br:5])[c:6]2[cH:7][c:8]([CH3:9])[c:10](-[c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]3[Cl:18])[n:19]2[n:20]1 | BrP(Br)Br.Cc1cc(O)c2cc(C)c(-c3ccc(Cl)cc3Cl)n2n1 | Cc1cc(Br)c2cc(C)c(-c3ccc(Cl)cc3Cl)n2n1 | null | null | BrC1=CC=CC=C1.C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | ff39b079d5712b2e8fb6051fea296d7ad7072dbbad8cafb15cf8deb18800be60 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(-c2ccc3cccnn23)cc1 | Br-P(-Br)-[Br;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C;D1;H3:5]):[#7;a:6]:[#7;a:7](:[c:8]):[c:9]:1:[c:10]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C;D1;H3:5]):[#7;a:6]:[#7;a:7](:[c:8]):[c:9]:1:[c:10] | null | [] | null | null | null | null | A solution of 7-(2,4-dichlorophenyl)-2,6-dimethylpyrrolo[1,2-b]pyridazin-4-ol (34.2 g, 111.5 mmol) and phosphorus tribromide (50 mL, 142.5 g, 526.4 mmol) in bromobenzene (500 mL) is refluxed for 1 h. After cooling to room temperature, the mixture is diluted with CHCl3. Saturated NaHCO3 solution is added at 0° C. to neu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cnn2cccc2c1 | c1cnn2cccc2c1 | c1cnn2cccc2c1.c1ccccc1 | HBr | BrC1=CC=CC=C1.C(Cl)(Cl)Cl | null | null | BrP(Br)Br.Cc1cc(O)c2cc(C)c(-c3ccc(Cl)cc3Cl)n2n1>BrC1=CC=CC=C1.C(Cl)(Cl)Cl>Cc1cc(Br)c2cc(C)c(-c3ccc(Cl)cc3Cl)n2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-75dba5912e8f4575b66e9d0fa05114ac | CCC(N)CC.Cc1cc(Br)c2cc(C)c(-c3ccc(Cl)cc3Cl)n2n1>>CCC(CC)Nc1cc(C)nn2c(-c3ccc(Cl)cc3Cl)c(C)cc12 | BrC=1C=2N(N=C(C1)C)C(=C(C2)C)C2=C(C=C(C=C2)Cl)Cl.C1(=CC=CC=C1)PC1=CC=CC=C1.C(=O)([O-])[O-].[Cs+].[Cs+].C(C)C(CC)N.C1(=CC=CC=C1)PC1=CC=CC=C1.C(C)C(CC)N>>ClC1=C(C=CC(=C1)Cl)C1=C(C=C2N1N=C(C=C2NC(CC)CC)C)C | [CH3:1][CH2:2][CH:3]([CH2:4][CH3:5])[NH2:6].Br[c:7]1[cH:8][c:9]([CH3:10])[n:11][n:12]2[c:13](-[c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]3[Cl:21])[c:22]([CH3:23])[cH:24][c:25]12>>[CH3:1][CH2:2][CH:3]([CH2:4][CH3:5])[NH:6][c:7]1[cH:8][c:9]([CH3:10])[n:11][n:12]2[c:13](-[c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][c... | CCC(N)CC.Cc1cc(Br)c2cc(C)c(-c3ccc(Cl)cc3Cl)n2n1 | CCC(CC)Nc1cc(C)nn2c(-c3ccc(Cl)cc3Cl)c(C)cc12 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O1CCOCC1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 7b4aa8211d99fef734da6c2f4e7ca387497d7f60a1c2445689c05518b4cf5c00 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2ccc3cccnn23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11](-[C:12])-[NH2;D1;+0:13]>>[C:10]-[C:11](-[C:12])-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | 5 | MINUTE | A mixture of 4-bromo-7-(2,4-dichlorophenyl)-2,6-dimethylpyrrolo[1,2-b]pyridazine (0.253 g, 0.683 mmol), 5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl](diphenyl)phosphine (0.043 g, 0.068 mmol), Cs2CO3 (0.311 g, 0.956 mmol) and Pd2(dba)3 (0.031 g, 0.034 mmol) in dioxane (7.0 mL) is stirred at room temperature for 5 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnn2cccc2c1 | c1cnn2cccc2c1 | c1ccccc1.c1cnn2cccc2c1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1 | null | 0.083333 | CCC(N)CC.Cc1cc(Br)c2cc(C)c(-c3ccc(Cl)cc3Cl)n2n1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1>CCC... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-612c05ec5c2e41d1a9c71169bc97def9 | COCC(N)COC.Cc1cc(Br)c2cc(C)c(-c3ccc(Cl)cc3Cl)n2n1>>COCC(COC)Nc1cc(C)nn2c(-c3ccc(Cl)cc3Cl)c(C)cc12 | COCC(COC)N.C1(CCCCC1)P(C1=C(C=CC=C1)C=1C(=CC=CC1)N(C)C)C1CCCCC1.BrC=1C=2N(N=C(C1)C)C(=C(C2)C)C2=C(C=C(C=C2)Cl)Cl.COCC(COC)N.C1(CCCCC1)P(C1=C(C=CC=C1)C=1C(=CC=CC1)N(C)C)C1CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>>ClC1=C(C=CC(=C1)Cl)C1=C(C=C2N1N=C(C=C2NC(COC)COC)C)C | [CH3:1][O:2][CH2:3][CH:4]([CH2:5][O:6][CH3:7])[NH2:8].Br[c:9]1[cH:10][c:11]([CH3:12])[n:13][n:14]2[c:15](-[c:16]3[cH:17][cH:18][c:19]([Cl:20])[cH:21][c:22]3[Cl:23])[c:24]([CH3:25])[cH:26][c:27]12>>[CH3:1][O:2][CH2:3][CH:4]([CH2:5][O:6][CH3:7])[NH:8][c:9]1[cH:10][c:11]([CH3:12])[n:13][n:14]2[c:15](-[c:16]3[cH:17][cH:18]... | COCC(N)COC.Cc1cc(Br)c2cc(C)c(-c3ccc(Cl)cc3Cl)n2n1 | COCC(COC)Nc1cc(C)nn2c(-c3ccc(Cl)cc3Cl)c(C)cc12 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | COCCOC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 7b4aa8211d99fef734da6c2f4e7ca387497d7f60a1c2445689c05518b4cf5c00 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2ccc3cccnn23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11](-[C:12])-[NH2;D1;+0:13]>>[C:10]-[C:11](-[C:12])-[NH;D2;+0:13]-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[#7;a:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | A mixture of 4-bromo-7-(2,4-dichlorophenyl)-2,6-dimethylpyrrolo[1,2-b]pyridazine (0.143 g, 0.387 mmol), 1,3-dimethoxypropan-2-amine (0.092 g, 0.774 mmol), 2′-(dicyclohexylphosphino)-N,N-dimethyl-1,1′-biphenyl-2-amine (0.011 g, 0.029 mmol), Cs2CO3 (0.176 g, 0.542 mmol) and Pd2(dba)3 (0.018 g, 0.02 mmol) in DME (5.0 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnn2cccc2c1 | c1cnn2cccc2c1 | c1ccccc1.c1cnn2cccc2c1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COCCOC | null | null | COCC(N)COC.Cc1cc(Br)c2cc(C)c(-c3ccc(Cl)cc3Cl)n2n1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].COCCOC>COC... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eeed86a1e6684f8f9caadda851bc0740 | C=C(C)CCl.CCOC(C)(O)OCC>>C=C(C)COC(C)(OCC)OCC | [H-].[Na+].C(C)OC(C)(O)OCC.C(C(C)=C)Cl>>C(C)OC(C)(OCC)OCC(C)=C | Cl[CH2:4][C:2](=[CH2:1])[CH3:3].[OH:5][C:6]([CH3:7])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13]>>[CH2:1]=[C:2]([CH3:3])[CH2:4][O:5][C:6]([CH3:7])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13] | C=C(C)CCl.CCOC(C)(O)OCC | C=C(C)COC(C)(OCC)OCC | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 9ef84a8c80411e848c10c5384ce78141e473ad5db44b97f46285876278d6d001 | 004868630acb495c3cf864467df50d8e3d3bf839809342ad5aeae72f8c34f6c8 | null | Cl-[CH2;D2;+0:1]-[C:2](=[C;D1;H2:3])-[C;D1;H3:4].[#8:5]-[C:6](-[#8:7])(-[C;D1;H3:8])-[OH;D1;+0:9]>>[#8:5]-[C:6](-[#8:7])(-[C;D1;H3:8])-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2](=[C;D1;H2:3])-[C;D1;H3:4] | 90 | [{"value": 90.0, "product": "C(C)OC(C)(OCC)OCC(C)=C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a cold (0° C.) suspension of NaH (2.68 g, 60%) in THF (150 mL) was added a solution of 1,1-diethoxyethanol [which was prepared according to the literature procedure of Zirkle, C. L. et. al. J. Org. Chem. 1961, 26, 395–407] (9.00 g) in THF (20 mL), and the reaction mixture was stirred at room temperature for 1 hour b... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary alcohol | Ether | null | null | null | HCl | C1CCOC1 | null | null | C=C(C)CCl.CCOC(C)(O)OCC>C1CCOC1>C=C(C)COC(C)(OCC)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-27a8acf820b94b2a9b5c234b63518568 | C=C(C)COC(C)(OCC)OCC.CCOC(C)=O>>CCOC(C)(OCC)OCC(C)=O | C(C)OC(C)(OCC)OCC(C)=C.CCOC(=O)C>>C(C)OC(C)(OCC(C)=O)OCC | C=[C:11]([CH2:10][O:9][C:4]([O:3][CH2:2][CH3:1])([CH3:5])[O:6][CH2:7][CH3:8])[CH3:12].CCOC(C)=[O:13]>>[CH3:1][CH2:2][O:3][C:4]([CH3:5])([O:6][CH2:7][CH3:8])[O:9][CH2:10][C:11]([CH3:12])=[O:13] | C=C(C)COC(C)(OCC)OCC.CCOC(C)=O | CCOC(C)(OCC)OCC(C)=O | null | null | null | Miscellaneous | OtherReaction | bc292b0288357b2a937ea84f024ba8d9150b3e3c9c101cd160c56ae820d122c2 | 5c14d692b47dc3a3876cd67890118ff3818be77bed9e4d9af560df791ea165f1 | null | C-C-O-C(-C)=[O;H0;D1;+0:1].C=[C;H0;D3;+0:2](-[C;D1;H3:3])-[C:4]-[#8:5]>>[#8:5]-[C:4]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[O;H0;D1;+0:1] | 82 | [{"value": 82.0, "product": "C(C)OC(C)(OCC(C)=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a cold (0° C.) suspension of NaH (2.68 g, 60%) in THF (150 mL) was added a solution of 1,1-diethoxyethanol [which was prepared according to the literature procedure of Zirkle, C. L. et. al. J. Org. Chem. 1961, 26, 395–407] (9.00 g) in THF (20 mL), and the reaction mixture was stirred at room temperature for 1 hour b... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Vinyl | Ketone | null | null | null | HO- | null | null | 8 | C=C(C)COC(C)(OCC)OCC.CCOC(C)=O>>CCOC(C)(OCC)OCC(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4d9422cf209442e1b9157087cf3a9eec | CCOC(=O)CC(C)=O.Nc1n[nH]cc1-c1ccc(Cl)cc1Cl>>Cc1cc(O)n2ncc(-c3ccc(Cl)cc3Cl)c2n1 | NC1=NNC=C1C1=C(C=C(C=C1)Cl)Cl.C(CC(=O)C)(=O)OCC>>ClC1=C(C=CC(=C1)Cl)C=1C=NN2C1N=C(C=C2O)C | CCO[C:4]([CH2:3][C:2](=O)[CH3:1])=[O:5].[n:6]1[nH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]2[Cl:17])[c:18]1[NH2:19]>>[CH3:1][c:2]1[cH:3][c:4]([OH:5])[n:6]2[n:7][cH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]3[Cl:17])[c:18]2[n:19]1 | CCOC(=O)CC(C)=O.Nc1n[nH]cc1-c1ccc(Cl)cc1Cl | Cc1cc(O)n2ncc(-c3ccc(Cl)cc3Cl)c2n1 | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | cf1b86977098d79b7be1ece6873bda7f30c6d01911ab0f65ca6847b1b18f1972 | e4cbab44abd9117eb42f959793b157d31b1dce9de3f9c3954c67bf975e572e43 | c1ccc(-c2cnn3cccnc23)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[C;D1;H3:5].[NH2;D1;+0:6]-[c:7]1:[c:8]:[c:9]:[nH;D2;+0:10]:[n;H0;D2;+0:11]:1>>[C;D1;H3:5]-[c;H0;D3;+0:4]1:[cH;D2;+0:3]:[c;H0;D3;+0:1](-[OH;D1;+0:2]):[n;H0;D3;+0:11]2:[n;H0;D2;+0:10]:[c:9]:[c:8]:[c:7]:2:[n;H0;D2;+0:6]:1 | null | [] | null | null | null | null | 3-Amino-4-(2,4-dichlorophenyl)pyrazole and ethyl acetoacetate (2 equivalents) were dissolved in dioxane and heated under reflux overnight. The mixture was concentrated in vacuo and diluted with ethyl acetate. An off-white solid formed after 2 days standing was collected by vacuum filtration, yielding 3-(2,4-dichlorophe... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Aromatic alcohol | c1cn[nH]c1 | c1cnc2ccnn2c1 | c1cnc2ccnn2c1.c1ccccc1 | HO- | O1CCOCC1 | null | null | CCOC(=O)CC(C)=O.Nc1n[nH]cc1-c1ccc(Cl)cc1Cl>O1CCOCC1>Cc1cc(O)n2ncc(-c3ccc(Cl)cc3Cl)c2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2156d1c017524a0cbee19821b8bddad0 | Cc1cc(O)n2nc(C)c(-c3ccc(N(C)C)nc3)c2n1.O=P(Cl)(Cl)Cl>>Cc1cc(Cl)n2nc(C)c(-c3ccc(N(C)C)nc3)c2n1 | CN(C1=NC=C(C=C1)C=1C(=NN2C1N=C(C=C2O)C)C)C.O=P(Cl)(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>>CN(C1=CC=C(C=N1)C=1C(=NN2C1N=C(C=C2Cl)C)C)C | O[c:4]1[cH:3][c:2]([CH3:1])[n:21][c:20]2[n:6]1[n:7][c:8]([CH3:9])[c:10]2-[c:11]1[cH:12][cH:13][c:14]([N:15]([CH3:16])[CH3:17])[n:18][cH:19]1.O=P(Cl)(Cl)[Cl:5]>>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[n:6]2[n:7][c:8]([CH3:9])[c:10](-[c:11]3[cH:12][cH:13][c:14]([N:15]([CH3:16])[CH3:17])[n:18][cH:19]3)[c:20]2[n:21]1 | Cc1cc(O)n2nc(C)c(-c3ccc(N(C)C)nc3)c2n1.O=P(Cl)(Cl)Cl | Cc1cc(Cl)n2nc(C)c(-c3ccc(N(C)C)nc3)c2n1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | 30db31a49fb136d312e5cd66a18ec0f0a14dbcb214980b33f05231569e6e02fd | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1cncc(-c2cnn3cccnc23)c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C;D1;H3:5]):[#7;a:6]:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[#7;a:11]:2:1>>[C;D1;H3:5]-[c:4]1:[#7;a:6]:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[#7;a:11]:2:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[c:3]:1 | null | [] | null | null | null | null | Intermediate 8 was dissolved in POCl3 (2 ml) and refluxed for 2 hours. The reaction mixture was cooled and poured onto ice. The solution was made basic (pH =9) by addition of solid sodium carbonate and extracted with diethyl ether. The combined organic layers were dried over sodium sulfate, filtered and concentrated, y... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1cnc2ccnn2c1.c1ccncc1 | HCl | null | null | null | Cc1cc(O)n2nc(C)c(-c3ccc(N(C)C)nc3)c2n1.O=P(Cl)(Cl)Cl>>Cc1cc(Cl)n2nc(C)c(-c3ccc(N(C)C)nc3)c2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6e017777e7694321af7690a84d3c006f | Cl>>Cl | Cl.CN(C1=CC(=C(C=N1)C=1C(=NN2C1N=C(C=C2N(CCC)CCC)C)C)C)C.Cl.CN(C1=CC(=C(C=N1)C=1C(=NN2C1N=C(C=C2N(CCC)CCC)C)C)C)C>>Cl.CN(C1=CC(=C(C=N1)C=1C(=NN2C1N=C(C=C2N(CCC)CCC)C)C)C)C | [ClH:29]>>[ClH:29] | Cl | Cl | null | null | C(Cl)Cl.C(C)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 98 | [{"value": 98.0, "product": "Cl.CN(C1=CC(=C(C=N1)C=1C(=NN2C1N=C(C=C2N(CCC)CCC)C)C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Compound 53 was also converted to its hydrochloric acid addition salt by dissolving compound 53 (8.1 g) in a mixture of diethyl ether (150 ml) and DCM (50 ml) and treating said mixture with HCl in diethyl ether (1 M, 21.3 ml) dropwise with stirring. The resulting off-white solid was collected by filtration, yielding 8.... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(Cl)Cl.C(C)OCC | null | null | Cl>C(Cl)Cl.C(C)OCC>Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ae3f8dbb508846458460d74a5e06fcf9 | O=C(Cl)CCCl.c1ccc2c(c1)CCN2>>O=C(CCCl)N1CCc2ccccc21 | N1CCC2=CC=CC=C12.C(C)N(CC)CC.ClCCC(=O)Cl>>ClCCC(=O)N1CCC2=CC=CC=C12 | Cl[C:2](=[O:1])[CH2:3][CH2:4][Cl:5].[NH:6]1[CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]21>>[O:1]=[C:2]([CH2:3][CH2:4][Cl:5])[N:6]1[CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]21 | O=C(Cl)CCCl.c1ccc2c(c1)CCN2 | O=C(CCCl)N1CCc2ccccc21 | null | null | O1CCCC1 | Acylation | N-alkylation of secondary amines with alkyl halides | a54af988dc8a0e6fa8c94962ffa120a4c8a47655c87b6249d21c160dad1c4f54 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc2c(c1)CCN2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[c:5]:[c:6]1:[c:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[c:7]:[c:6]-1:[c:5] | null | [] | 10 | CELSIUS | null | null | A mixture of 2,3-dihydro-1H-indole (50 g), triethylamine (132 g) and tetrahydrofuran (1000 mL) was cooled down to 10° C. followed by the addition (over a period of 60 min) of a solution of 3-chloropropanoyl chloride (55 g) in tetrahydrofuran (400 mL). The mixture was filtered, and the remaining solution was evaporated ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | HCl | O1CCCC1 | 10 | null | O=C(Cl)CCCl.c1ccc2c(c1)CCN2>O1CCCC1>O=C(CCCl)N1CCc2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d3a524826c144ae7a4391a161a3c47f7 | O=C(Cl)CCCCl.c1ccc2c(c1)CCN2>>O=C(CCCCl)N1CCc2ccccc21 | N1CCC2=CC=CC=C12.ClCCCC(=O)Cl>>ClCCCC(=O)N1CCC2=CC=CC=C12 | Cl[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][Cl:6].[NH:7]1[CH2:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]21>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][Cl:6])[N:7]1[CH2:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]21 | O=C(Cl)CCCCl.c1ccc2c(c1)CCN2 | O=C(CCCCl)N1CCc2ccccc21 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | a54af988dc8a0e6fa8c94962ffa120a4c8a47655c87b6249d21c160dad1c4f54 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc2c(c1)CCN2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[c:5]:[c:6]1:[c:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[c:7]:[c:6]-1:[c:5] | null | [] | null | null | null | null | from 2,3-dihydro-1H-indole and 4-chlorobutanoyl chloride
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | HCl | null | null | null | O=C(Cl)CCCCl.c1ccc2c(c1)CCN2>>O=C(CCCCl)N1CCc2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8927a7fafdc34fe5a65e186a76ac0ebf | O=C(Cl)CCCCBr.c1ccc2c(c1)CCN2>>O=C(CCCCBr)N1CCc2ccccc21 | N1CCC2=CC=CC=C12.BrCCCCC(=O)Cl>>BrCCCCC(=O)N1CCC2=CC=CC=C12 | Cl[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][CH2:6][Br:7].[NH:8]1[CH2:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][CH2:6][Br:7])[N:8]1[CH2:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]21 | O=C(Cl)CCCCBr.c1ccc2c(c1)CCN2 | O=C(CCCCBr)N1CCc2ccccc21 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | a54af988dc8a0e6fa8c94962ffa120a4c8a47655c87b6249d21c160dad1c4f54 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc2c(c1)CCN2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[c:5]:[c:6]1:[c:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[c:7]:[c:6]-1:[c:5] | null | [] | null | null | null | null | from 2,3-dihydro-1H-indole and 5-bromopentanoyl chloride
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | HCl | null | null | null | O=C(Cl)CCCCBr.c1ccc2c(c1)CCN2>>O=C(CCCCBr)N1CCc2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6d65ec534f0a41f98f5231e8018591cb | NNc1ccc(F)cc1.O=CCCCCCl>>Fc1ccc2[nH]cc(CCCCl)c2c1 | P(O)(O)(O)=O.ClCCCCC=O.Cl.FC1=CC=C(C=C1)NN.C1(=CC=CC=C1)C>>ClCCCC1=CNC2=CC=C(C=C12)F | N[NH:6][c:5]1[cH:4][cH:3][c:2]([F:1])[cH:14][cH:13]1.O=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11][Cl:12]>>[F:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][cH:7][c:8]([CH2:9][CH2:10][CH2:11][Cl:12])[c:13]2[cH:14]1 | NNc1ccc(F)cc1.O=CCCCCCl | Fc1ccc2[nH]cc(CCCCl)c2c1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 4c28518fc88ec2e861e2b49903fd43bb056f0a993696cb766272ba6bb12d67f0 | 611c3e56c6946eaed630b4073459f41d6d3a61372803fe7ee67c41f4faa161cd | c1ccc2[nH]ccc2c1 | N-[NH;D2;+0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].O=[CH;D2;+0:7]-[CH2;D2;+0:8]-[C:9]-[C:10]>>[C:10]-[C:9]-[c;H0;D3;+0:8]1:[cH;D2;+0:7]:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4]:1:[c:5]:[c:6] | null | [] | null | null | 15 | MINUTE | The compound 5-chloropentan-1-ol (16.2 mL) was dissolved in cold 5 mM 2,2,6,6-tetramethylpiperidine-1-yloxy (tempo) in dichloromethane (240 mL) and cooled down to 0° C. with an ice bath. Potassium bromide (0.5 M in water, 24 mL) was added, and this was followed by the addition (in one portion at 5° C. under vigorous st... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aldehyde | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | O | null | 0.25 | NNc1ccc(F)cc1.O=CCCCCCl>O>Fc1ccc2[nH]cc(CCCCl)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-370a6cbbe6c54647b332523ff0ceb3f5 | NNc1ccc(F)cc1.OCCCCCCCl>>Fc1ccc2[nH]cc(CCCCCl)c2c1 | ClCCCCCCO.Cl.FC1=CC=C(C=C1)NN>>ClCCCCC1=CNC2=CC=C(C=C12)F | N[NH:6][c:5]1[cH:4][cH:3][c:2]([F:1])[cH:15][cH:14]1.O[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][Cl:13]>>[F:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][cH:7][c:8]([CH2:9][CH2:10][CH2:11][CH2:12][Cl:13])[c:14]2[cH:15]1 | NNc1ccc(F)cc1.OCCCCCCCl | Fc1ccc2[nH]cc(CCCCCl)c2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 57b4ef29f6533e3c4b72380daff525f7a55da2c5aa3638e75c40d89e69b343d2 | 949182d4d3d2a116ebbe9c2bbc14a94f3ad8f06f100f80cebcd83e748e7d2ae5 | c1ccc2[nH]ccc2c1 | N-[NH;D2;+0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].O-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[C:9]-[C:10]>>[C:10]-[C:9]-[c;H0;D3;+0:8]1:[cH;D2;+0:7]:[nH;D2;+0:1]:[c:2](:[c:3]):[c;H0;D3;+0:4]:1:[c:5]:[c:6] | null | [] | null | null | null | null | from 6-chlorohexan-1-ol and 4-fluorophenylhydrazine hydrochloride
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary alcohol | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | null | null | null | NNc1ccc(F)cc1.OCCCCCCCl>>Fc1ccc2[nH]cc(CCCCCl)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5cf14fa7563d49d78e92d52b25a29237 | BrCCCCBr.O=C1CCc2ccccc2N1>>O=C1CCc2ccccc2N1CCCCBr | BrCCCCBr.[H-].[Na+].N1C(CCC2=CC=CC=C12)=O>>BrCCCCN1C(CCC2=CC=CC=C12)=O | Br[CH2:12][CH2:13][CH2:14][CH2:15][Br:16].[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[NH:11]1>>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][Br:16] | BrCCCCBr.O=C1CCc2ccccc2N1 | O=C1CCc2ccccc2N1CCCCBr | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e7b4b186b3651fd15b60671427dc34c5cd6cb02aa0116a7c1fd6c1cf6f406256 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=C1CCc2ccccc2N1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[C:5](=[O;D1;H0:6])-[C:4])-[c:8](:[c:9]):[c:10] | 75.1 | [{"value": 75.1, "product": "BrCCCCN1C(CCC2=CC=CC=C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A suspension of sodium hydride (6.8 g, 60% dispersion in mineral oil) and dimethyl formamide (200 mL) was kept at 20–30° C. followed by the addition of a solution of 3,4-dihydroquinolin-2(1H)-one (25 g) in dimethyl formamide (100 mL). The resulting mixture was stirred at room temperature for 30 min followed by the addi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2 | HBr | CN(C=O)C | null | 0.5 | BrCCCCBr.O=C1CCc2ccccc2N1>CN(C=O)C>O=C1CCc2ccccc2N1CCCCBr |
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