dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e9f16d4033b3426ca548f02ccc0c2b35 | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl.Cc1ccc(NS(N)(=O)=O)nc1>>COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccc(C)cn1 | CC=1C=CC(=NC1)NS(=O)(=O)N.ClC1=NC(=NC(=C1OC1=C(C=CC=C1)OC)Cl)C1=CC=NC=C1>>ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=NC=C(C=C1)C)(=O)=O)OC1=C(C=CC=C1)OC | Cl[c:22]1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:11]([Cl:12])[n:13][c:14](-[c:15]2[cH:16][cH:17][n:18][cH:19][cH:20]2)[n:21]1.[NH2:23][S:24](=[O:25])(=[O:26])[NH:27][c:28]1[cH:29][cH:30][c:31]([CH3:32])[cH:33][n:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[c:11]([Cl:12])[... | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl.Cc1ccc(NS(N)(=O)=O)nc1 | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccc(C)cn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 345edf40ad678aea0250ec5b3d6cc512d8eac020b2f4324f423c18b59726753e | e7974806b40218fa965bb62bf9c430cac38870897b20726116f8b48ae128dc55 | O=S(=O)(Nc1ccccn1)Nc1nc(-c2ccncc2)ncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1-[#8:9].[#7:10]-[#16:11](-[NH2;D1;+0:12])(=[O;D1;H0:13])=[O;D1;H0:14]>>[#7:10]-[#16:11](=[O;D1;H0:13])(=[O;D1;H0:14])-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1-[#8:9] | 17 | [{"value": 17.0, "product": "ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=NC=C(C=C1)C)(=O)=O)OC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the procedure described in referential Example 1e), 5-methyl-pyridine-2-sulfamic acid amide (252 mg, Referential Example 20) was reacted with 4,6-dichloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidine (410 mg, Referential Example 1d)) to give 5-methyl-pyridine-2-sulfamic acid-[6-chloro-5-(o-methoxyphenoxy)... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide | Sulfonamide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1.c1ccncc1 | HCl | null | null | null | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl.Cc1ccc(NS(N)(=O)=O)nc1>>COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccc(C)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3a2f19201fb4458e938ba790074c31b8 | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl.NS(=O)(=O)Nc1ccccn1>>COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccccn1 | N1=C(C=CC=C1)NS(=O)(=O)N.ClC1=NC(=NC(=C1OC1=C(C=CC=C1)OC)Cl)C1=CC=NC=C1>>ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=NC=CC=C1)(=O)=O)OC1=C(C=CC=C1)OC | Cl[c:22]1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:11]([Cl:12])[n:13][c:14](-[c:15]2[cH:16][cH:17][n:18][cH:19][cH:20]2)[n:21]1.[NH2:23][S:24](=[O:25])(=[O:26])[NH:27][c:28]1[cH:29][cH:30][cH:31][cH:32][n:33]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[c:11]([Cl:12])[n:13][c:1... | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl.NS(=O)(=O)Nc1ccccn1 | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccccn1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 345edf40ad678aea0250ec5b3d6cc512d8eac020b2f4324f423c18b59726753e | e7974806b40218fa965bb62bf9c430cac38870897b20726116f8b48ae128dc55 | O=S(=O)(Nc1ccccn1)Nc1nc(-c2ccncc2)ncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1-[#8:9].[#7:10]-[#16:11](-[NH2;D1;+0:12])(=[O;D1;H0:13])=[O;D1;H0:14]>>[#7:10]-[#16:11](=[O;D1;H0:13])(=[O;D1;H0:14])-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1-[#8:9] | 71.8 | [{"value": 71.8, "product": "ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=NC=CC=C1)(=O)=O)OC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the procedure described in referential Example 1e), pyridine-2-sulfamic acid amide (60 mg, Referential Example 21) was reacted with 4,6-dichloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidine (100 mg, Referential Example 1d)) to give pyridine-2-sulfamic acid-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-4-py... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide | Sulfonamide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1.c1ccncc1 | HCl | null | null | null | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl.NS(=O)(=O)Nc1ccccn1>>COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9ec8837a87b248b2b9999eaadda6b40a | CCNS(N)(=O)=O.COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl>>COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccccn1 | C(C)NS(N)(=O)=O.ClC1=NC(=NC(=C1OC1=C(C=CC=C1)OC)Cl)C1=CC=NC=C1>>ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=NC=CC=C1)(=O)=O)OC1=C(C=CC=C1)OC | [NH2:23][S:24](=[O:25])(=[O:26])[NH:33][CH2:29][CH3:30].Cl[c:32]1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:11]([Cl:12])[n:13][c:14](-[c:15]2[cH:16][cH:17][n:18][cH:19][cH:20]2)[n:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[c:11]([Cl:12])[n:13][c:14](-[c:15]2[cH:16][cH:17][... | CCNS(N)(=O)=O.COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccccn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 283ee355c481da0ae43e8a4ead3e293aa3222fc998e480675e520fef4ed3791e | 6303949decfda2ee299bbf5557020af70d269ae23a015f9213b4396280149edd | O=S(=O)(Nc1ccccn1)Nc1nc(-c2ccncc2)ncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c;H0;D3;+0:8]:1-[#8:9]-[c:10].[CH3;D1;+0:11]-[CH2;D2;+0:12]-[NH;D2;+0:13]-[S;H0;D4;+0:14](-[NH2;D1;+0:15])(=[O;D1;H0:16])=[O;D1;H0:17]>>[Cl;D1;H0:7]-[c:6]1:[#7;a:5]:[c:3](-[c:4]):[n;H0;D2;+0:2]:[c:18](-[NH;D2;+0:15]-[S;H0;D4;+0:14](=[O;D1;H0... | 100.5 | [{"value": 100.5, "product": "ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=NC=CC=C1)(=O)=O)OC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the procedure described in referential Example 1e), ethyl-sulfamic acid amide (40 mg, Referential Example 22) was reacted with 4,6-dichloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidine (100 mg, Referential Example 1d)) to give pyridine-2-sulfamic acid-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-4-pyrimid... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Sulfonamide.Aromatic halide.Ether | Sulfonamide.Sulfonamide.Ether | c1cncnc1 | c1cncnc1.c1ccncc1 | c1ccccc1.c1cncnc1.c1ccncc1.c1ccncc1 | HCl | null | null | null | CCNS(N)(=O)=O.COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl>>COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-74338b5aed30449facdcc0ace8215f09 | Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.Cc1ccc(NS(N)(=O)=O)cc1>>Cc1ccc(NS(=O)(=O)Nc2ncnc(Cl)c2-c2ccc(C)cc2)cc1 | C(C)(C)N(CC)C(C)C.ClC1=NC=NC(=C1C1=CC=C(C=C1)C)Cl.[K].CC1=CC=C(C=C1)NS(N)(=O)=O>>ClC1=C(C(=NC=N1)NS(NC1=CC=C(C=C1)C)(=O)=O)C1=CC=C(C=C1)C | Cl[c:11]1[n:12][cH:13][n:14][c:15]([Cl:16])[c:17]1-[c:18]1[cH:19][cH:20][c:21]([CH3:22])[cH:23][cH:24]1.[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][S:7](=[O:8])(=[O:9])[NH2:10])[cH:25][cH:26]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][S:7](=[O:8])(=[O:9])[NH:10][c:11]2[n:12][cH:13][n:14][c:15]([Cl:16])[c:17]2-[c:18]2[cH:19][cH:... | Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.Cc1ccc(NS(N)(=O)=O)cc1 | Cc1ccc(NS(=O)(=O)Nc2ncnc(Cl)c2-c2ccc(C)cc2)cc1 | null | null | CO.CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 345edf40ad678aea0250ec5b3d6cc512d8eac020b2f4324f423c18b59726753e | e7974806b40218fa965bb62bf9c430cac38870897b20726116f8b48ae128dc55 | O=S(=O)(Nc1ccccc1)Nc1ncncc1-c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[c:8].[#7:9]-[#16:10](-[NH2;D1;+0:11])(=[O;D1;H0:12])=[O;D1;H0:13]>>[#7:9]-[#16:10](=[O;D1;H0:12])(=[O;D1;H0:13])-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[c:8] | 62.1 | [{"value": 62.1, "product": "ClC1=C(C(=NC=N1)NS(NC1=CC=C(C=C1)C)(=O)=O)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | To 4,6-dichloro-5-p-tolyl-pyrimidine (Referential Example 7) (2.0 g) dissolved in DMSO (35 ml) was added di-isopropyl-ethyl-amine (1.46 ml) followed by addition of 4-methyl-phenyl sulfamic acid amide potassium salt (2.78 g) [prepared from the product described in Referential Example 19 and potassium tert.-butylate in m... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide | Sulfonamide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | CO.CS(=O)C | null | 48 | Cc1ccc(-c2c(Cl)ncnc2Cl)cc1.Cc1ccc(NS(N)(=O)=O)cc1>CO.CS(=O)C>Cc1ccc(NS(=O)(=O)Nc2ncnc(Cl)c2-c2ccc(C)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-101c7ac50baf4d4999c44b012e398b23 | Clc1ccc(-c2c(Cl)ncnc2Cl)cc1.NS(=O)(=O)NCc1ccccc1>>O=S(=O)(NCc1ccccc1)Nc1ncnc(Cl)c1-c1ccc(Cl)cc1 | C(C)(C)N(CC)C(C)C.ClC1=NC=NC(=C1C1=CC=C(C=C1)Cl)Cl.[K].C(C1=CC=CC=C1)NS(N)(=O)=O>>ClC1=C(C(=NC=N1)NS(NCC1=CC=CC=C1)(=O)=O)C1=CC=C(C=C1)Cl | Cl[c:13]1[n:14][cH:15][n:16][c:17]([Cl:18])[c:19]1-[c:20]1[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]1.[O:1]=[S:2](=[O:3])([NH:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[NH2:12]>>[O:1]=[S:2](=[O:3])([NH:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[NH:12][c:13]1[n:14][cH:15][n:16][c:17]([Cl:18])[c:19]1-[c:20... | Clc1ccc(-c2c(Cl)ncnc2Cl)cc1.NS(=O)(=O)NCc1ccccc1 | O=S(=O)(NCc1ccccc1)Nc1ncnc(Cl)c1-c1ccc(Cl)cc1 | null | null | CO.CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 345edf40ad678aea0250ec5b3d6cc512d8eac020b2f4324f423c18b59726753e | e7974806b40218fa965bb62bf9c430cac38870897b20726116f8b48ae128dc55 | O=S(=O)(NCc1ccccc1)Nc1ncncc1-c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[c:8].[#7:9]-[#16:10](-[NH2;D1;+0:11])(=[O;D1;H0:12])=[O;D1;H0:13]>>[#7:9]-[#16:10](=[O;D1;H0:12])(=[O;D1;H0:13])-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[c:8] | 44.1 | [{"value": 44.1, "product": "ClC1=C(C(=NC=N1)NS(NCC1=CC=CC=C1)(=O)=O)C1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To 4,6-dichloro-5-(4-chloro-phenyl)-pyrimidine (Referential Example 9) (2.59 g) dissolved in DMSO (14 ml) was added di-isopropyl-ethyl-amine (1.8 ml) followed by the addition of benzyl sulfamic acid amide potassium salt (2.25 g) [prepared from the product described in Referential Example 22 and potassium tert.-butylate... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide | Sulfonamide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | CO.CS(=O)C | null | 24 | Clc1ccc(-c2c(Cl)ncnc2Cl)cc1.NS(=O)(=O)NCc1ccccc1>CO.CS(=O)C>O=S(=O)(NCc1ccccc1)Nc1ncnc(Cl)c1-c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3f15be0b70554171a09e916b132ee286 | CO.COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccc(C(C)C)cc1>>COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OC | ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC.CO.C1CCOC1.[H-].[Na+]>>COC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC | [OH:36][CH3:37].Cl[c:35]1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:11]([NH:12][S:13](=[O:14])(=[O:15])[NH:16][c:17]2[cH:18][cH:19][c:20]([CH:21]([CH3:22])[CH3:23])[cH:24][cH:25]2)[n:26][c:27](-[c:28]2[cH:29][cH:30][n:31][cH:32][cH:33]2)[n:34]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:... | CO.COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccc(C(C)C)cc1 | COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 320b907a829de2b489cb2f69345494f41d68001a72a3955182cde184381510f6 | 23dafde907f7a74dc1d4cc65967b00a9b318897fe61a3d3c4a9fddf320485f17 | O=S(=O)(Nc1ccccc1)Nc1nc(-c2ccncc2)ncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[#7:7]):[c:8]:1-[#8:9].[C;D1;H3:10]-[OH;D1;+0:11]>>[#7:7]-[c:6]1:[#7;a:5]:[c:3](-[c:4]):[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:11]-[C;D1;H3:10]):[c:8]:1-[#8:9] | null | [] | 80 | CELSIUS | null | null | To a mixture of methanol (1 ml) and THF (2 ml) was added sodium hydride (100 mg, 60% dispersion in mineral oil) followed by the addition of 4-i-propyl-phenyl sulfamic acid-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide (100 mg, Referential Example 1e)). DMF (0.5 ml) was added and the reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Methanol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1ccncc1 | HCl | CN(C)C=O | 80 | null | CO.COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccc(C(C)C)cc1>CN(C)C=O>COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a308b8d7315b46f3a3735372c111dddd | C=CCO.COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccc(C(C)C)cc1>>C=CCOc1nc(-c2ccncc2)nc(NS(=O)(=O)Nc2ccc(C(C)C)cc2)c1Oc1ccccc1OC | ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC.C(C=C)O.C1CCOC1.[H-].[Na+]>>C(C=C)OC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC | [CH2:1]=[CH:2][CH2:3][OH:4].Cl[c:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][n:11][cH:12][cH:13]2)[n:14][c:15]([NH:16][S:17](=[O:18])(=[O:19])[NH:20][c:21]2[cH:22][cH:23][c:24]([CH:25]([CH3:26])[CH3:27])[cH:28][cH:29]2)[c:30]1[O:31][c:32]1[cH:33][cH:34][cH:35][cH:36][c:37]1[O:38][CH3:39]>>[CH2:1]=[CH:2][CH2:3][O:4][c:5]1[n:6][c... | C=CCO.COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccc(C(C)C)cc1 | C=CCOc1nc(-c2ccncc2)nc(NS(=O)(=O)Nc2ccc(C(C)C)cc2)c1Oc1ccccc1OC | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1ccccc1)Nc1nc(-c2ccncc2)ncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1-[#8:8].[C;D1;H2:9]=[C:10]-[C:11]-[OH;D1;+0:12]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:12]-[C:11]-[C:10]=[C;D1;H2:9]):[c:7]:1-[#8:8] | null | [] | 80 | CELSIUS | null | null | To a mixture of allyl alcohol (1 ml) and THF (2 ml) was added sodium hydride (100 mg, 60% dispersion in mineral oil) followed by the addition of 4-i-propyl-phenyl sulfamic acid-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide (100 mg, Referential Example 1e)). DMF (0.5 ml) was added and the reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccncc1.c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | 80 | null | C=CCO.COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccc(C(C)C)cc1>CN(C)C=O>C=CCOc1nc(-c2ccncc2)nc(NS(=O)(=O)Nc2ccc(C(C)C)cc2)c1Oc1ccccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd381fa9f51b40b4a02d97a29218a03d | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccc(C(C)C)cc1.OCCO>>COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCO | [H-].[Na+].C(CO)O.ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC>>OCCOC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC | Cl[c:35]1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:11]([NH:12][S:13](=[O:14])(=[O:15])[NH:16][c:17]2[cH:18][cH:19][c:20]([CH:21]([CH3:22])[CH3:23])[cH:24][cH:25]2)[n:26][c:27](-[c:28]2[cH:29][cH:30][n:31][cH:32][cH:33]2)[n:34]1.[OH:36][CH2:37][CH2:38][OH:39]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6]... | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccc(C(C)C)cc1.OCCO | COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCO | null | null | C(OC)COC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1ccccc1)Nc1nc(-c2ccncc2)ncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[#7:7]):[c:8]:1-[#8:9].[C:10]-[C:11]-[OH;D1;+0:12]>>[#7:7]-[c:6]1:[#7;a:5]:[c:3](-[c:4]):[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:12]-[C:11]-[C:10]):[c:8]:1-[#8:9] | null | [] | 80 | CELSIUS | 30 | MINUTE | Sodium hydride (17 mg, 60% dispersion in mineral oil) was added to ethylene glycol (1.2 ml) followed by addition of dimethoxyethane (0.5 ml). Stirring was continued for 30 min, then 4-i-propyl-phenyl sulfamic acid-[6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide (45 mg, Referential Example 1e)) was ad... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1ccncc1 | HCl | C(OC)COC | 80 | 0.5 | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1NS(=O)(=O)Nc1ccc(C(C)C)cc1.OCCO>C(OC)COC>COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fd75d1250ff34f74a530d064642bf2d5 | COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCO.Clc1ncccn1>>COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCOc1ncccn1 | CN(C)C=O.[H-].[Na+].OCCOC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC.ClC1=NC=CC=N1>>N1=C(N=CC=C1)OCCOC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[c:11]([NH:12][S:13](=[O:14])(=[O:15])[NH:16][c:17]2[cH:18][cH:19][c:20]([CH:21]([CH3:22])[CH3:23])[cH:24][cH:25]2)[n:26][c:27](-[c:28]2[cH:29][cH:30][n:31][cH:32][cH:33]2)[n:34][c:35]1[O:36][CH2:37][CH2:38][OH:39].Cl[c:40]1[n:41][cH:42][cH:43][cH:44][n:45]1>>... | COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCO.Clc1ncccn1 | COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCOc1ncccn1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1ccccc1)Nc1nc(-c2ccncc2)nc(OCCOc2ncccn2)c1Oc1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 73 | [{"value": 73.0, "product": "N1=C(N=CC=C1)OCCOC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 10 | MINUTE | 4-i-Propyl-phenyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide (60 mg, Example 3) was dissolved in THF (8 ml) and sodium hydride (14 mg, 60% dispersion in mineral oil) was added and stirring continued for 10 min. 2-Chloro-pyrimidine (22 mg) was added and the mixture was h... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1ccncc1.c1cncnc1 | HCl | C1CCOC1 | 60 | 0.166667 | COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCO.Clc1ncccn1>C1CCOC1>COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCOc1ncccn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a2a3024b09cf491db1828fcf80ec430e | COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCO.Clc1ncc(Br)cn1>>COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCOc1ncc(Br)cn1 | CN(C)C=O.OCCOC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC.[H-].[Na+].BrC=1C=NC(=NC1)Cl>>BrC=1C=NC(=NC1)OCCOC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[c:11]([NH:12][S:13](=[O:14])(=[O:15])[NH:16][c:17]2[cH:18][cH:19][c:20]([CH:21]([CH3:22])[CH3:23])[cH:24][cH:25]2)[n:26][c:27](-[c:28]2[cH:29][cH:30][n:31][cH:32][cH:33]2)[n:34][c:35]1[O:36][CH2:37][CH2:38][OH:39].Cl[c:40]1[n:41][cH:42][c:43]([Br:44])[cH:45][... | COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCO.Clc1ncc(Br)cn1 | COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCOc1ncc(Br)cn1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1ccccc1)Nc1nc(-c2ccncc2)nc(OCCOc2ncccn2)c1Oc1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 71.9 | [{"value": 71.9, "product": "BrC=1C=NC(=NC1)OCCOC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 10 | MINUTE | 4-i-Propyl-phenyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide (60 mg, Example 3) was dissoved in THF (8 ml). Sodium hydride (14 mg, 60% dispersion in mineral oil) was added and stirring continued for 10 min. 5-Bromo-2-chloro-pyrimidine (37 mg) was added and the mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1ccncc1.c1cncnc1 | HCl | C1CCOC1 | 60 | 0.166667 | COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCO.Clc1ncc(Br)cn1>C1CCOC1>COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCOc1ncc(Br)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d0ced6154e874d9fa7cf2d92247c694c | COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCO.FC(F)(F)c1ccc(Cl)nc1>>COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCOc1ccc(C(F)(F)F)cn1 | OCCOC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC.[H-].[Na+].FC(C=1C=CC(=NC1)Cl)(F)F>>FC(C=1C=CC(=NC1)OCCOC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC)(F)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[c:11]([NH:12][S:13](=[O:14])(=[O:15])[NH:16][c:17]2[cH:18][cH:19][c:20]([CH:21]([CH3:22])[CH3:23])[cH:24][cH:25]2)[n:26][c:27](-[c:28]2[cH:29][cH:30][n:31][cH:32][cH:33]2)[n:34][c:35]1[O:36][CH2:37][CH2:38][OH:39].Cl[c:40]1[cH:41][cH:42][c:43]([C:44]([F:45])(... | COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCO.FC(F)(F)c1ccc(Cl)nc1 | COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCOc1ccc(C(F)(F)F)cn1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | ea617b323b892eda23f5ae30e789991ea9692064ef355a16e8ed81c16e743d2b | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1ccccc1)Nc1nc(-c2ccncc2)nc(OCCOc2ccccn2)c1Oc1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 64.9 | [{"value": 64.9, "product": "FC(C=1C=CC(=NC1)OCCOC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NC1=CC=C(C=C1)C(C)C)(=O)=O)OC1=C(C=CC=C1)OC)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 10 | MINUTE | 4-i-Propyl-phenyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide (50 mg, Example 3) was dissolved in THF (8 ml). Sodium hydride (12 mg, 60% dispersion in mineral oil) was added and stirring continued for 10 min. 5-Trifluoromethyl-2-chloro-pyridine (28 mg) was added and the ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1ccncc1.c1ccncc1 | HCl | C1CCOC1 | 60 | 0.166667 | COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCO.FC(F)(F)c1ccc(Cl)nc1>C1CCOC1>COc1ccccc1Oc1c(NS(=O)(=O)Nc2ccc(C(C)C)cc2)nc(-c2ccncc2)nc1OCCOc1ccc(C(F)(F)F)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-54c27a8b69d64090a7bc68f329ae5eb1 | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl.N>>COc1ccccc1Oc1c(N)nc(-c2ccncc2)nc1Cl | ClC1=NC(=NC(=C1OC1=C(C=CC=C1)OC)Cl)C1=CC=NC=C1.N.N>>NC1=NC(=NC(=C1OC1=C(C=CC=C1)OC)Cl)C1=CC=NC=C1 | Cl[c:11]1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:22]([Cl:23])[n:21][c:14](-[c:15]2[cH:16][cH:17][n:18][cH:19][cH:20]2)[n:13]1.[NH3:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[c:11]([NH2:12])[n:13][c:14](-[c:15]2[cH:16][cH:17][n:18][cH:19][cH:20]2)[n:21][c:22]1[Cl:23] | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl.N | COc1ccccc1Oc1c(N)nc(-c2ccncc2)nc1Cl | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 90f3138935f3ad06434c84a4ac47f6a17b2b61711b0b3fffea5d29513d5b1a76 | c5668f64a1395fa45312378ed819baaeafc354cdb673b20226ea2853ed14db5d | c1ccc(Oc2cnc(-c3ccncc3)nc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1-[#8:9].[NH3;D0;+0:10]>>[#8:9]-[c:8]1:[c:6](-[Cl;D1;H0:7]):[#7;a:5]:[c:3](-[c:4]):[#7;a:2]:[c;H0;D3;+0:1]:1-[NH2;D1;+0:10] | null | [] | null | null | 18 | HOUR | 4,6-Dichloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidine (2.9 g, Referential Example 1d)) was suspended in dioxane (30 ml) and ammonia (gaseous) was introduced until the solution was saturated. Stirring was continued for 7 days while the saturation of the reaction mixture with ammonia (gaseous) was repeated every 16 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Primary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1 | HCl | O1CCOCC1 | null | 18 | COc1ccccc1Oc1c(Cl)nc(-c2ccncc2)nc1Cl.N>O1CCOCC1>COc1ccccc1Oc1c(N)nc(-c2ccncc2)nc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8747ffbddac545759a82510b3d14071c | CCNS(=O)(=O)Cl.COc1ccccc1Oc1c(N)nc(-c2ccncc2)nc1Cl>>CCNS(=O)(=O)Nc1nc(-c2ccncc2)nc(Cl)c1Oc1ccccc1OC | NC1=NC(=NC(=C1OC1=C(C=CC=C1)OC)Cl)C1=CC=NC=C1.C1CCC2=NCCCN2CC1.C(C)NS(=O)(=O)Cl>>ClC1=C(C(=NC(=N1)C1=CC=NC=C1)NS(NCC)(=O)=O)OC1=C(C=CC=C1)OC | Cl[S:4]([NH:3][CH2:2][CH3:1])(=[O:5])=[O:6].[NH2:7][c:8]1[n:9][c:10](-[c:11]2[cH:12][cH:13][n:14][cH:15][cH:16]2)[n:17][c:18]([Cl:19])[c:20]1[O:21][c:22]1[cH:23][cH:24][cH:25][cH:26][c:27]1[O:28][CH3:29]>>[CH3:1][CH2:2][NH:3][S:4](=[O:5])(=[O:6])[NH:7][c:8]1[n:9][c:10](-[c:11]2[cH:12][cH:13][n:14][cH:15][cH:16]2)[n:17]... | CCNS(=O)(=O)Cl.COc1ccccc1Oc1c(N)nc(-c2ccncc2)nc1Cl | CCNS(=O)(=O)Nc1nc(-c2ccncc2)nc(Cl)c1Oc1ccccc1OC | null | CN(C)C=1C=CN=CC1 | C1CCOC1.C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 79f8c5b4a38a78326b06fe818d16a864d10a3b32cd34e300057e08f5b58776e1 | 6630e3d6dc8a83d080e6361e8a6265158c2c9e15f17c9dff1184e40b54fc124d | c1ccc(Oc2cnc(-c3ccncc3)nc2)cc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[#7:4]-[C:5].[NH2;D1;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1>>[C:5]-[#7:4]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1 | null | [] | null | null | 12 | HOUR | 4-Amino-6-chloro-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidine (100 mg) was dissolved in THF (5 ml) and DCM (5 ml). DBU (46 mg) and DMAP (37 mg) were added followed by the addition of ethyl-sulfamoylchloride (prepared from ethylamine hydrochloride and sulfuryl chloride). The mixture was stirred for 12 h at r.t. The sol... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Primary amine | Sulfonamide.Sulfonamide | null | null | c1cncnc1.c1ccncc1.c1ccccc1 | HCl | CN(C)C=1C=CN=CC1.C1CCOC1.C(Cl)Cl | null | 12 | CCNS(=O)(=O)Cl.COc1ccccc1Oc1c(N)nc(-c2ccncc2)nc1Cl>CN(C)C=1C=CN=CC1.C1CCOC1.C(Cl)Cl>CCNS(=O)(=O)Nc1nc(-c2ccncc2)nc(Cl)c1Oc1ccccc1OC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-542f35727f4d4e29a5f0506e1410f87a | Cc1ccc(NS(=O)(=O)Nc2ncnc(Cl)c2-c2ccc(C)cc2)cc1.OCCO>>Cc1ccc(NS(=O)(=O)Nc2ncnc(OCCO)c2-c2ccc(C)cc2)cc1 | [Na].ClC1=C(C(=NC=N1)NS(NC1=CC=C(C=C1)C)(=O)=O)C1=CC=C(C=C1)C.COCCOC.C(CO)O.[Na]>>OCCOC1=C(C(=NC=N1)NS(NC1=CC=C(C=C1)C)(=O)=O)C1=CC=C(C=C1)C | Cl[c:15]1[n:14][cH:13][n:12][c:11]([NH:10][S:7]([NH:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:29][cH:28]2)(=[O:8])=[O:9])[c:20]1-[c:21]1[cH:22][cH:23][c:24]([CH3:25])[cH:26][cH:27]1.[OH:16][CH2:17][CH2:18][OH:19]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][S:7](=[O:8])(=[O:9])[NH:10][c:11]2[n:12][cH:13][n:14][c:15]([O:16][CH2:1... | Cc1ccc(NS(=O)(=O)Nc2ncnc(Cl)c2-c2ccc(C)cc2)cc1.OCCO | Cc1ccc(NS(=O)(=O)Nc2ncnc(OCCO)c2-c2ccc(C)cc2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1ccccc1)Nc1ncncc1-c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1-[c:8].[C:9]-[C:10]-[OH;D1;+0:11]>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:11]-[C:10]-[C:9]):[c:7]:1-[c:8] | null | [] | null | null | 4 | DAY | To a mixture of 1,2-dimethoxyethan (15 ml) and ethyleneglycol (40 ml) was added sodium (298 mg) in small portions. The mixture was stirred until the sodium was completely dissolved. Then DMF (15 ml), followed by 4-methyl-phenyl sulfamic acid-[6-chloro-5-(p-tolyl)-4-pyrimidinyl]-amide (1.0 g, Referential Example 14) was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | CN(C)C=O | null | 96 | Cc1ccc(NS(=O)(=O)Nc2ncnc(Cl)c2-c2ccc(C)cc2)cc1.OCCO>CN(C)C=O>Cc1ccc(NS(=O)(=O)Nc2ncnc(OCCO)c2-c2ccc(C)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-10a552460a6a408ea1a49c7fdf62806f | Cc1ccc(NS(=O)(=O)Nc2ncnc(OCCO)c2-c2ccc(C)cc2)cc1.Clc1ncc(Br)cn1>>Cc1ccc(NS(=O)(=O)Nc2ncnc(OCCOc3ncc(Br)cn3)c2-c2ccc(C)cc2)cc1 | C(CC(O)(C(=O)O)CC(=O)O)(=O)O.[H-].[Na+].OCCOC1=C(C(=NC=N1)NS(NC1=CC=C(C=C1)C)(=O)=O)C1=CC=C(C=C1)C.BrC=1C=NC(=NC1)Cl>>BrC=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)NS(NC1=CC=C(C=C1)C)(=O)=O)C1=CC=C(C=C1)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][S:7](=[O:8])(=[O:9])[NH:10][c:11]2[n:12][cH:13][n:14][c:15]([O:16][CH2:17][CH2:18][OH:19])[c:27]2-[c:28]2[cH:29][cH:30][c:31]([CH3:32])[cH:33][cH:34]2)[cH:35][cH:36]1.Cl[c:20]1[n:21][cH:22][c:23]([Br:24])[cH:25][n:26]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][S:7](=[O:8])(=[O:9])[NH:... | Cc1ccc(NS(=O)(=O)Nc2ncnc(OCCO)c2-c2ccc(C)cc2)cc1.Clc1ncc(Br)cn1 | Cc1ccc(NS(=O)(=O)Nc2ncnc(OCCOc3ncc(Br)cn3)c2-c2ccc(C)cc2)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(Nc1ccccc1)Nc1ncnc(OCCOc2ncccn2)c1-c1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 52.5 | [{"value": 52.5, "product": "BrC=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)NS(NC1=CC=C(C=C1)C)(=O)=O)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To 4-methyl-phenyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(p-tolyl)-4-pyrimidinyl]-amide (47 mg, Example 11) dissolved in THF (8 ml) was added sodium hydride (14.6 mg, 60% dispersion in mineral oil) and stirring was continued for 15 min followed by the addition of 5-bromo-2-chloro-pyrimidine (39 mg). Stirring was contin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1cncnc1.c1ccccc1 | HCl | C1CCOC1 | null | 0.25 | Cc1ccc(NS(=O)(=O)Nc2ncnc(OCCO)c2-c2ccc(C)cc2)cc1.Clc1ncc(Br)cn1>C1CCOC1>Cc1ccc(NS(=O)(=O)Nc2ncnc(OCCOc3ncc(Br)cn3)c2-c2ccc(C)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-acd75006bb814bdab99020ebd9053b27 | O=C(O)CC(O)(CC(=O)O)C(=O)O.O=S(=O)(NCc1ccccc1)Nc1ncnc(Cl)c1-c1ccc(Cl)cc1>>O=S(=O)(NCc1ccccc1)Nc1ncnc(OCCO)c1-c1ccc(Cl)cc1 | CC(C)([O-])C.[K+].ClC1=C(C(=NC=N1)NS(NCC1=CC=CC=C1)(=O)=O)C1=CC=C(C=C1)Cl.C(CC(O)(C(=O)O)CC(=O)O)(=O)O>>OCCOC1=C(C(=NC=N1)NS(NCC1=CC=CC=C1)(=O)=O)C1=CC=C(C=C1)Cl | O=C(O)CC(C(=O)O)([OH:18])[CH2:19][C:20](=O)[OH:21].Cl[c:17]1[n:16][cH:15][n:14][c:13]([NH:12][S:2](=[O:1])(=[O:3])[NH:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:22]1-[c:23]1[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]1>>[O:1]=[S:2](=[O:3])([NH:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[NH:12][c:13]1[n:14... | O=C(O)CC(O)(CC(=O)O)C(=O)O.O=S(=O)(NCc1ccccc1)Nc1ncnc(Cl)c1-c1ccc(Cl)cc1 | O=S(=O)(NCc1ccccc1)Nc1ncnc(OCCO)c1-c1ccc(Cl)cc1 | null | null | C(CO)O | Heteroatom Alkylation and Arylation | OtherReaction | b18ba87fb2ec0987a978e901bb5a53033e53fbf47b9296eda6a432ff7972ccf1 | 0d57d11c1ca6b9fbb36ccec54ea803b423eb00045b608c0a6b2fdbd90fbd86af | O=S(=O)(NCc1ccccc1)Nc1ncncc1-c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[c:7]:1-[c:8].O-C(=O)-C-C(-[OH;D1;+0:9])(-[CH2;D2;+0:10]-[C;H0;D3;+0:11](=O)-[O;D1;H1:12])-C(-O)=O>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[O;D1;H1:12]):[c:7]:1-[c:8] | null | [] | 102 | CELSIUS | null | null | Potassium tert.-butoxide (3.5 g) was dissolved in ethyleneglycol (35 ml), benzyl sulfamic acid-[6-chloro-5-(4-chlorophenyl)-4-pyrimidinyl]-amide (1.8 g, Referential Example 15) was added and the mixture was heated to 102° C. for 11 h. The mixture was poured onto ice/water and acidified to pH=4 with solid citric acid. T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Carboxylic acid.Carboxylic acid.Tertiary alcohol | Ether.Primary alcohol | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | C(CO)O | 102 | null | O=C(O)CC(O)(CC(=O)O)C(=O)O.O=S(=O)(NCc1ccccc1)Nc1ncnc(Cl)c1-c1ccc(Cl)cc1>C(CO)O>O=S(=O)(NCc1ccccc1)Nc1ncnc(OCCO)c1-c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fbd7d5ace7f143329a76ff9d61c40004 | COc1ccccc1Oc1c(Cl)nc(SC)nc1Cl.NS(=O)(=O)NCc1ccccc1>>COc1ccccc1Oc1c(Cl)nc(SC)nc1NS(=O)(=O)NCc1ccccc1 | ClC1=NC(=NC(=C1OC1=C(C=CC=C1)OC)Cl)SC.[K].C(C1=CC=CC=C1)NS(N)(=O)=O.C(CC(O)(C(=O)O)CC(=O)O)(=O)O>>ClC1=C(C(=NC(=N1)SC)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC=C1)OC | Cl[c:18]1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:11]([Cl:12])[n:13][c:14]([S:15][CH3:16])[n:17]1.[NH2:19][S:20](=[O:21])(=[O:22])[NH:23][CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[c:11]([Cl:12])[n:13][c:14]([S:15][CH3:16])[n... | COc1ccccc1Oc1c(Cl)nc(SC)nc1Cl.NS(=O)(=O)NCc1ccccc1 | COc1ccccc1Oc1c(Cl)nc(SC)nc1NS(=O)(=O)NCc1ccccc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 345edf40ad678aea0250ec5b3d6cc512d8eac020b2f4324f423c18b59726753e | e7974806b40218fa965bb62bf9c430cac38870897b20726116f8b48ae128dc55 | O=S(=O)(NCc1ccccc1)Nc1ncncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1-[#8:9].[#7:10]-[#16:11](-[NH2;D1;+0:12])(=[O;D1;H0:13])=[O;D1;H0:14]>>[#16:4]-[c:3]1:[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8](-[#8:9]):[c;H0;D3;+0:1](-[NH;D2;+0:12]-[#16:11](-[#7:10])(=[O;D1;H0:13])=[O;D1;H0:14]):[#7;a:2]:1 | 79.2 | [{"value": 79.2, "product": "ClC1=C(C(=NC(=N1)SC)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 18 | HOUR | 4,6-Dichloro-5-(2-methoxy-phenoxy)-2-methylsulfanyl-pyrimidine (1.5 g) was dissolved in DMSO (30 ml) and benzylsulfamic acid amide potassium salt (2.12 g, Referential Example 22) was added. Stirring was continued for 18 h. The reaction mixture was poured onto water, acidified by solid citric acid (1.9 g), cooled to 0° ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide | Sulfonamide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | CS(=O)C | 0 | 18 | COc1ccccc1Oc1c(Cl)nc(SC)nc1Cl.NS(=O)(=O)NCc1ccccc1>CS(=O)C>COc1ccccc1Oc1c(Cl)nc(SC)nc1NS(=O)(=O)NCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6ee78f80b18e4ed883b42873c9de4f88 | COc1ccccc1Oc1c(Cl)nc(SC)nc1NS(=O)(=O)NCc1ccccc1.O=C(O)CC(O)(CC(=O)O)C(=O)O>>COc1ccccc1Oc1c(NS(=O)(=O)NCc2ccccc2)nc(SC)nc1OCCO | ClC1=C(C(=NC(=N1)SC)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC=C1)OC.C(CC(O)(C(=O)O)CC(=O)O)(=O)O>>OCCOC1=C(C(=NC(=N1)SC)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC=C1)OC | Cl[c:29]1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:11]([NH:12][S:13](=[O:14])(=[O:15])[NH:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24][c:25]([S:26][CH3:27])[n:28]1.O=C(O)C(O)(C[C:31](=O)[OH:30])C[C:32](=O)[OH:33]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[c:11... | COc1ccccc1Oc1c(Cl)nc(SC)nc1NS(=O)(=O)NCc1ccccc1.O=C(O)CC(O)(CC(=O)O)C(=O)O | COc1ccccc1Oc1c(NS(=O)(=O)NCc2ccccc2)nc(SC)nc1OCCO | null | null | C(CO)O | Heteroatom Alkylation and Arylation | OtherReaction | b18ba87fb2ec0987a978e901bb5a53033e53fbf47b9296eda6a432ff7972ccf1 | 0d57d11c1ca6b9fbb36ccec54ea803b423eb00045b608c0a6b2fdbd90fbd86af | O=S(=O)(NCc1ccccc1)Nc1ncncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6](-[#7:7]):[c:8]:1-[#8:9].O-C(=O)-C(-O)(-C-[C;H0;D3;+0:10](=O)-[OH;D1;+0:11])-C-[C;H0;D3;+0:12](=O)-[O;D1;H1:13]>>[#16:4]-[c:3]1:[#7;a:5]:[c:6](-[#7:7]):[c:8](-[#8:9]):[c;H0;D3;+0:1](-[O;H0;D2;+0:11]-[CH2;D2;+0:10]-[CH2;D2;+0:12]-[O;D1;H1:13]):[#7;a:2]:1 | null | [] | 100 | CELSIUS | 40 | HOUR | Benzylsulfamic acid [6-chloro-5-(2-methoxy-phenoxy)-2-methylsulfanyl-pyrimidin-4-yl]-amide (1.75 g) was added to a solution of potassium tert.-butylate (1.87 g) in ethylene glycol (30 ml) and stirred at 100° C. for 40 h. The reaction mixture was poured onto water (120 ml), acidified with solid citric acid (1.9 g) and c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Carboxylic acid.Carboxylic acid.Tertiary alcohol | Ether.Primary alcohol | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1 | HCl | C(CO)O | 100 | 40 | COc1ccccc1Oc1c(Cl)nc(SC)nc1NS(=O)(=O)NCc1ccccc1.O=C(O)CC(O)(CC(=O)O)C(=O)O>C(CO)O>COc1ccccc1Oc1c(NS(=O)(=O)NCc2ccccc2)nc(SC)nc1OCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c351c2e4f8214539a2c6c19c44d24359 | C1COCCN1.COc1ccccc1Oc1c(NS(=O)(=O)NCc2ccccc2)nc(S(C)(=O)=O)nc1OCCO>>COc1ccccc1Oc1c(NS(=O)(=O)NCc2ccccc2)nc(N2CCOCC2)nc1OCCO | OCCOC1=C(C(=NC(=N1)S(=O)(=O)C)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC=C1)OC.N1CCOCC1.C(CC(O)(C(=O)O)CC(=O)O)(=O)O>>OCCOC1=C(C(=NC(=N1)N1CCOCC1)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC=C1)OC | [NH:26]1[CH2:27][CH2:28][O:29][CH2:30][CH2:31]1.CS(=O)(=O)[c:25]1[n:24][c:11]([NH:12][S:13](=[O:14])(=[O:15])[NH:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:33]([O:34][CH2:35][CH2:36][OH:37])[n:32]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][... | C1COCCN1.COc1ccccc1Oc1c(NS(=O)(=O)NCc2ccccc2)nc(S(C)(=O)=O)nc1OCCO | COc1ccccc1Oc1c(NS(=O)(=O)NCc2ccccc2)nc(N2CCOCC2)nc1OCCO | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | a229bf13f557504c39a1f354abc763ba9cdeb25f6d32f8670bca8649cb0049f3 | 22da100633727aad1f507a5545a4789af97f1ba2143d8d6cef2b1c60e063c167 | O=S(=O)(NCc1ccccc1)Nc1nc(N2CCOCC2)ncc1Oc1ccccc1 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1):[#7;a:4]:[c:5] | null | [] | 45 | CELSIUS | 48 | HOUR | Benzylsulfamic acid [6-(2-hydroxy-ethoxy)-2-methanesulfonyl-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide (85 mg) were dissolved in THF (2 ml) and morpholine (2 ml) was added. The reaction mixture was stirred at 45° C. for 48 hours, poured onto water, acidified with solid citric acid and extracted with EtOAc (2×). The co... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfone | Tertiary amine | C1COCCN1.c1cncnc1 | c1cncnc1.C1COCC[NH]1 | c1ccccc1.c1ccccc1.c1cncnc1.C1COCC[NH]1 | HO- | C1CCOC1 | 45 | 48 | C1COCCN1.COc1ccccc1Oc1c(NS(=O)(=O)NCc2ccccc2)nc(S(C)(=O)=O)nc1OCCO>C1CCOC1>COc1ccccc1Oc1c(NS(=O)(=O)NCc2ccccc2)nc(N2CCOCC2)nc1OCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8294d5b564034b9ba886a31d576bed35 | COc1ccccc1Oc1c(Cl)nc(-c2ccnc(C#N)c2)nc1Cl.NS(=O)(=O)NCc1ccccc1>>COc1ccccc1Oc1c(Cl)nc(-c2ccnc(C#N)c2)nc1NS(=O)(=O)NCc1ccccc1 | C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(C)N(C(C)C)C(C)C.[K].C(C1=CC=CC=C1)NS(N)(=O)=O.ClC1=NC(=NC(=C1OC1=C(C=CC=C1)OC)Cl)C1=CC(=NC=C1)C#N>>ClC1=C(C(=NC(=N1)C1=CC(=NC=C1)C#N)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC=C1)OC | Cl[c:24]1[c:10]([O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[c:11]([Cl:12])[n:13][c:14](-[c:15]2[cH:16][cH:17][n:18][c:19]([C:20]#[N:21])[cH:22]2)[n:23]1.[NH2:25][S:26](=[O:27])(=[O:28])[NH:29][CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[c... | COc1ccccc1Oc1c(Cl)nc(-c2ccnc(C#N)c2)nc1Cl.NS(=O)(=O)NCc1ccccc1 | COc1ccccc1Oc1c(Cl)nc(-c2ccnc(C#N)c2)nc1NS(=O)(=O)NCc1ccccc1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 345edf40ad678aea0250ec5b3d6cc512d8eac020b2f4324f423c18b59726753e | e7974806b40218fa965bb62bf9c430cac38870897b20726116f8b48ae128dc55 | O=S(=O)(NCc1ccccc1)Nc1nc(-c2ccncc2)ncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1-[#8:9].[#7:10]-[#16:11](-[NH2;D1;+0:12])(=[O;D1;H0:13])=[O;D1;H0:14]>>[#7:10]-[#16:11](=[O;D1;H0:13])(=[O;D1;H0:14])-[NH;D2;+0:12]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1-[#8:9] | 93 | [{"value": 93.0, "product": "ClC1=C(C(=NC(=N1)C1=CC(=NC=C1)C#N)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | 4-[4,6-Dichloro-5-(2-methoxy-phenoxy)-pyrimidin-2-yl]-pyridine-2-carbonitrile (3.2 g) was dissolved in DMSO (20 ml), N-ethyidiisopropylamine (1.7 ml) and benzylsulfamic acid amide potassium salt (3.52 g) was added. The mixture was stirred for 18 h at rt, poured onto ice/water, acidified with solid citric acid and the p... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide | Sulfonamide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccncc1.c1ccccc1 | HCl | CS(=O)C | null | 18 | COc1ccccc1Oc1c(Cl)nc(-c2ccnc(C#N)c2)nc1Cl.NS(=O)(=O)NCc1ccccc1>CS(=O)C>COc1ccccc1Oc1c(Cl)nc(-c2ccnc(C#N)c2)nc1NS(=O)(=O)NCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0b976c54799a443abc1b8ade62e50a2f | COc1ccccc1Oc1c(Cl)nc(-c2ccnc(C#N)c2)nc1NS(=O)(=O)NCc1ccccc1.[N-]=[N+]=[N-]>>COc1ccccc1Oc1c(Cl)nc(-c2ccnc(-c3nnn[nH]3)c2)nc1NS(=O)(=O)NCc1ccccc1 | ClC1=C(C(=NC(=N1)C1=CC(=NC=C1)C#N)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC=C1)OC.[N-]=[N+]=[N-].[Na+].[Cl-].[NH4+]>>ClC1=C(C(=NC(=N1)C1=CC(=NC=C1)C1=NN=NN1)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[c:11]([Cl:12])[n:13][c:14](-[c:15]2[cH:16][cH:17][n:18][c:19]([C:20]#[N:21])[cH:25]2)[n:26][c:27]1[NH:28][S:29](=[O:30])(=[O:31])[NH:32][CH2:33][c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1.[N-:22]=[N+:23]=[N-:24]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8... | COc1ccccc1Oc1c(Cl)nc(-c2ccnc(C#N)c2)nc1NS(=O)(=O)NCc1ccccc1.[N-]=[N+]=[N-] | COc1ccccc1Oc1c(Cl)nc(-c2ccnc(-c3nnn[nH]3)c2)nc1NS(=O)(=O)NCc1ccccc1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 237b84aaa459abf427f233dc6a07a1d9de824f980714e458423189bb68f60f12 | d8c808528b7ee68720aaeebd35cb6a2a30e344748d0066102cdae99843b93cf0 | O=S(=O)(NCc1ccccc1)Nc1nc(-c2ccnc(-c3nnn[nH]3)c2)ncc1Oc1ccccc1 | [N-;H0;D1:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[c:9]:[c:10]>>[c:10]:[c:9]:[c;H0;D3;+0:6](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:1]:[n;H0;D2;+0:2]:[nH;D2;+0:3]:1):[#7;a:7]:[c:8] | 37 | [{"value": 37.0, "product": "ClC1=C(C(=NC(=N1)C1=CC(=NC=C1)C1=NN=NN1)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 20 | HOUR | Benzylsulfamic acid [6-chloro-2-(2-cyano-pyridin-4-yl)-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide (4.17 g) was dissolved in DMF (55 ml). Sodium azide (5.2 g) and ammonium chloride (4.28 g) were added and the mixture was stirred for 20 h at 80° C. Then the mixture was pored onto water and extracted with EtOAc. The laye... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | null | c1nnn[nH]1 | c1ccccc1.c1cncnc1.c1ccncc1.c1nnn[nH]1.c1ccccc1 | null | CN(C)C=O | 80 | 20 | COc1ccccc1Oc1c(Cl)nc(-c2ccnc(C#N)c2)nc1NS(=O)(=O)NCc1ccccc1.[N-]=[N+]=[N-]>CN(C)C=O>COc1ccccc1Oc1c(Cl)nc(-c2ccnc(-c3nnn[nH]3)c2)nc1NS(=O)(=O)NCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-55d92de5fa0c4851ae06f9bff61c1f14 | COc1ccc(Cl)c(OC(C(=O)O)C(=O)O)c1.N=CN>>COc1ccc(Cl)c(Oc2c(O)ncnc2O)c1 | ClC1=C(OC(C(=O)O)C(=O)O)C=C(C=C1)OC.Cl.C(=N)N>>ClC1=C(OC=2C(=NC=NC2O)O)C=C(C=C1)OC | O=[C:11]([CH:10]([O:9][c:8]1[c:6]([Cl:7])[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:18]1)[C:16](=O)[OH:17])[OH:12].[NH:13]=[CH:14][NH2:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[c:8]([O:9][c:10]2[c:11]([OH:12])[n:13][cH:14][n:15][c:16]2[OH:17])[cH:18]1 | COc1ccc(Cl)c(OC(C(=O)O)C(=O)O)c1.N=CN | COc1ccc(Cl)c(Oc2c(O)ncnc2O)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b03631945f38bf302aeee4b9f74f85e65141b7a66cb69031caf004ec327f3dc0 | 31fac4e42cb8aa63b4d4c94f3c0d3cc94f37f20fca6f96719ed2a4be2a06cc7e | c1ccc(Oc2cncnc2)cc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[CH;D3;+0:3](-[#8:4]-[c:5])-[C;H0;D3;+0:6](=O)-[O;D1;H1:7].[NH2;D1;+0:8]-[CH;D2;+0:9]=[NH;D1;+0:10]>>[O;D1;H1:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[cH;D2;+0:9]:[n;H0;D2;+0:8]:[c;H0;D3;+0:6](-[O;D1;H1:7]):[c;H0;D3;+0:3]:1-[#8:4]-[c:5] | null | [] | null | null | null | null | 5-(2-Chloro-5-methoxy-phenoxy)-pyrimidine-4,6-diol was prepared from 2-(2-chloro-5-methoxy-phenoxy)-malonic acid dimnethyl ster and formamidine hydrochloride according to the procedure described in Referential Example 1c.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Ether.Primary amine | Ether.Aromatic alcohol.Aromatic alcohol | null | c1cncnc1 | c1ccccc1.c1cncnc1 | HO- | null | null | null | COc1ccc(Cl)c(OC(C(=O)O)C(=O)O)c1.N=CN>>COc1ccc(Cl)c(Oc2c(O)ncnc2O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-829e83a9265c4f86b928d2636b829e73 | COc1ccc(Cl)c(Oc2c(Cl)ncnc2Cl)c1.NS(=O)(=O)NCc1ccccc1>>COc1ccc(Cl)c(Oc2c(Cl)ncnc2NS(=O)(=O)NCc2ccccc2)c1 | ClC1=NC=NC(=C1OC1=C(C=CC(=C1)OC)Cl)Cl.[K].C(C1=CC=CC=C1)NS(N)(=O)=O>>ClC1=C(C(=NC=N1)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC(=C1)OC)Cl | Cl[c:16]1[c:10]([O:9][c:8]2[c:6]([Cl:7])[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:29]2)[c:11]([Cl:12])[n:13][cH:14][n:15]1.[NH2:17][S:18](=[O:19])(=[O:20])[NH:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[c:8]([O:9][c:10]2[c:11]([Cl:12])[n:13][cH:14][n:15][c:16]2[NH:17][S:... | COc1ccc(Cl)c(Oc2c(Cl)ncnc2Cl)c1.NS(=O)(=O)NCc1ccccc1 | COc1ccc(Cl)c(Oc2c(Cl)ncnc2NS(=O)(=O)NCc2ccccc2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 345edf40ad678aea0250ec5b3d6cc512d8eac020b2f4324f423c18b59726753e | e7974806b40218fa965bb62bf9c430cac38870897b20726116f8b48ae128dc55 | O=S(=O)(NCc1ccccc1)Nc1ncncc1Oc1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[#8:8].[#7:9]-[#16:10](-[NH2;D1;+0:11])(=[O;D1;H0:12])=[O;D1;H0:13]>>[#7:9]-[#16:10](=[O;D1;H0:12])(=[O;D1;H0:13])-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[#8:8] | 47 | [{"value": 47.0, "product": "ClC1=C(C(=NC=N1)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC(=C1)OC)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Benzylsulfamic acid [6-chloro-5-(2-chloro-5-methoxy-phenoxy)-pyrimidin-4-yl]-amide (0.7 g) was prepared from 4,6-dichloro-5-(2-chloro-5-methoxy-phenoxy)-pyrimidine (1 g) and benzylsulfamic acid amide potassium salt (1.21 g) according to the procedure described in Referential Example 15. LC-MS: tR=5.13; [M+H]+=456.91.
C... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Aromatic halide | Sulfonamide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | null | null | null | COc1ccc(Cl)c(Oc2c(Cl)ncnc2Cl)c1.NS(=O)(=O)NCc1ccccc1>>COc1ccc(Cl)c(Oc2c(Cl)ncnc2NS(=O)(=O)NCc2ccccc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3bb0dfd1ce95456b8756fcc5434fcc41 | COc1ccc(Cl)c(Oc2c(NS(=O)(=O)NCc3ccccc3)ncnc2OCCO)c1.Clc1ncc(Br)cn1>>COc1ccc(Cl)c(Oc2c(NS(=O)(=O)NCc3ccccc3)ncnc2OCCOc2ncc(Br)cn2)c1 | ClC1=C(OC=2C(=NC=NC2OCCO)NS(NCC2=CC=CC=C2)(=O)=O)C=C(C=C1)OC.BrC=1C=NC(=NC1)Cl>>BrC=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC(=C1)OC)Cl | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[c:8]([O:9][c:10]2[c:11]([NH:12][S:13](=[O:14])(=[O:15])[NH:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[n:24][cH:25][n:26][c:27]2[O:28][CH2:29][CH2:30][OH:31])[cH:39]1.Cl[c:32]1[n:33][cH:34][c:35]([Br:36])[cH:37][n:38]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[... | COc1ccc(Cl)c(Oc2c(NS(=O)(=O)NCc3ccccc3)ncnc2OCCO)c1.Clc1ncc(Br)cn1 | COc1ccc(Cl)c(Oc2c(NS(=O)(=O)NCc3ccccc3)ncnc2OCCOc2ncc(Br)cn2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(NCc1ccccc1)Nc1ncnc(OCCOc2ncccn2)c1Oc1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 48.4 | [{"value": 48.4, "product": "BrC=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC(=C1)OC)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Benzylsulfamic acid [6-[2-(5-bromo-pyrimidin-2-yloxy)-ethoxy]-5-(2-chloro-5-methoxy-phenoxy)-pyrimidin-4-yl]-amide (77 mg) (Example 212) was prepared from benzylsulfamic acid [5-(2-chloro-5-methoxy-phenoxy)-6-(2-hydroxy-ethoxy)-pyrimidin-4-yl]-amide (120 mg) (Example 211) and 5-bromo-2-chloropyrimidine (100 mg) accordi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1 | HCl | null | null | null | COc1ccc(Cl)c(Oc2c(NS(=O)(=O)NCc3ccccc3)ncnc2OCCO)c1.Clc1ncc(Br)cn1>>COc1ccc(Cl)c(Oc2c(NS(=O)(=O)NCc3ccccc3)ncnc2OCCOc2ncc(Br)cn2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0557e87742a0462f9f27941c55dcda0f | COc1ccc(Cl)c(Oc2c(NS(=O)(=O)NCc3ccccc3)ncnc2OCCO)c1.CSc1cnc(Cl)nc1>>COc1ccc(Cl)c(Oc2c(NS(=O)(=O)NCc3ccccc3)ncnc2OCCOc2ncc(SC)cn2)c1 | ClC1=C(OC=2C(=NC=NC2OCCO)NS(NCC2=CC=CC=C2)(=O)=O)C=C(C=C1)OC.CSC=1C=NC(=NC1)Cl>>CSC=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC(=C1)OC)Cl | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[c:8]([O:9][c:10]2[c:11]([NH:12][S:13](=[O:14])(=[O:15])[NH:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[n:24][cH:25][n:26][c:27]2[O:28][CH2:29][CH2:30][OH:31])[cH:40]1.Cl[c:32]1[n:33][cH:34][c:35]([S:36][CH3:37])[cH:38][n:39]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([... | COc1ccc(Cl)c(Oc2c(NS(=O)(=O)NCc3ccccc3)ncnc2OCCO)c1.CSc1cnc(Cl)nc1 | COc1ccc(Cl)c(Oc2c(NS(=O)(=O)NCc3ccccc3)ncnc2OCCOc2ncc(SC)cn2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(NCc1ccccc1)Nc1ncnc(OCCOc2ncccn2)c1Oc1ccccc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[OH;D1;+0:8]>>[C:6]-[C:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 45.7 | [{"value": 45.7, "product": "CSC=1C=NC(=NC1)OCCOC1=C(C(=NC=N1)NS(NCC1=CC=CC=C1)(=O)=O)OC1=C(C=CC(=C1)OC)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Benzylsulfamic acid [6-[2-(5-methylsulfanyl-pyrimidin-2-yloxy)-ethoxy]-5-(2-chloro-5-methoxy-phenoxy)-pyrimidin-4-yl]-amide (138 mg) (Example 213) was prepared from benzylsulfamic acid [5-(2-chloro-5-methoxy-phenoxy)-6-(2-hydroxy-ethoxy)-pyrimidin-4-yl]-amide (240 mg) (Example 211) and 5-methylsulfanyl-2-chloropyrimidi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1ccccc1.c1cncnc1.c1cncnc1 | HCl | null | null | null | COc1ccc(Cl)c(Oc2c(NS(=O)(=O)NCc3ccccc3)ncnc2OCCO)c1.CSc1cnc(Cl)nc1>>COc1ccc(Cl)c(Oc2c(NS(=O)(=O)NCc3ccccc3)ncnc2OCCOc2ncc(SC)cn2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e23d6a74247b400bb87430ce70adc43b | CCO.O=C(O)c1cc(F)c(F)c(F)c1F>>CCOC(=O)c1cc(F)c(F)c(F)c1F | C(=O)(O)[O-].[Na+].C(C)O.FC1=C(C(=O)O)C=C(C(=C1F)F)F.C(C(=O)Cl)(=O)Cl>>C(C)OC(C1=C(C(=C(C(=C1)F)F)F)F)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]([F:13])[c:14]1[F:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]([F:13])[c:14]1[F:15] | CCO.O=C(O)c1cc(F)c(F)c(F)c1F | CCOC(=O)c1cc(F)c(F)c(F)c1F | null | CN(C=O)C | ClCCl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 100.3 | [{"value": 100.3, "product": "C(C)OC(C1=C(C(=C(C(=C1)F)F)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | MINUTE | A solution of 2,3,4,5-tetrafluorobenzoic acid (4.68 g, 24.1 mmol) in dichloromethane (50 mL) at 0° C. is treated with oxalyl chloride (11.5 mL, 132 mmol) followed by N,N-dimethylformamide (4 drops). The mixture is stirred at 0° C. for 5 minutes and then at room temperature for 1.5 hours. The mixture is concentrated to ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C=O)C.ClCCl | 0 | 0.083333 | CCO.O=C(O)c1cc(F)c(F)c(F)c1F>CN(C=O)C.ClCCl>CCOC(=O)c1cc(F)c(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-58a59fa4c9c44e9090ed4436fa020b49 | CCO.O=C(O)c1c(F)cc(F)c(F)c1F>>CCOC(=O)c1c(F)cc(F)c(F)c1F | C(C)O.C(=O)(O)[O-].[Na+].C(C(=O)Cl)(=O)Cl.FC1=C(C(=O)O)C(=CC(=C1F)F)F>>C(C)OC(C1=C(C(=C(C=C1F)F)F)F)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[c:7]([F:8])[cH:9][c:10]([F:11])[c:12]([F:13])[c:14]1[F:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([F:8])[cH:9][c:10]([F:11])[c:12]([F:13])[c:14]1[F:15] | CCO.O=C(O)c1c(F)cc(F)c(F)c1F | CCOC(=O)c1c(F)cc(F)c(F)c1F | null | CN(C=O)C | ClCCl.C1=CC=CC=C1 | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 60.1 | [{"value": 60.1, "product": "C(C)OC(C1=C(C(=C(C=C1F)F)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 2,3,4,6-Tetrafluorobenzoic acid (4.8 g, 24.7 mmol) in dichloromethane (80 mL) is cooled to 0° C. under a nitrogen atmosphere and treated with oxalyl chloride (11.2 mL, 128 mmol) followed by anhydrous N,N-dimethylformamide (2 drops). The mixture is warmed to room temperature and stirred for 2 hours. The solution is co-e... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C=O)C.ClCCl.C1=CC=CC=C1 | null | 2 | CCO.O=C(O)c1c(F)cc(F)c(F)c1F>CN(C=O)C.ClCCl.C1=CC=CC=C1>CCOC(=O)c1c(F)cc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5a1e87024e2c4043be3cf1af09546602 | CCO.O=C(O)c1cc(F)c(F)c(Cl)c1F>>CCOC(=O)c1cc(F)c(F)c(Cl)c1F | ClC=1C(=C(C(=O)O)C=C(C1F)F)F.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C)OC(C1=C(C(=C(C(=C1)F)F)Cl)F)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]([Cl:13])[c:14]1[F:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]([Cl:13])[c:14]1[F:15] | CCO.O=C(O)c1cc(F)c(F)c(Cl)c1F | CCOC(=O)c1cc(F)c(F)c(Cl)c1F | null | CN(C=O)C | ClCCl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 100.6 | [{"value": 100.6, "product": "C(C)OC(C1=C(C(=C(C(=C1)F)F)Cl)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | To a solution of 3-chloro-2,4,5-trifluorobenzoic acid (Example 20, 4.90 g, 23.3 mmol) in dichloromethane (50 mL) is added oxalyl chloride (5.1 mL, 58.2 mmol) and N,N-dimethylformamide (1 drop). After 45 minutes, the reaction mixture is concentrated under vacuum. The resulting residue is dissolved in dichloromethane (50... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C=O)C.ClCCl | null | 0.75 | CCO.O=C(O)c1cc(F)c(F)c(Cl)c1F>CN(C=O)C.ClCCl>CCOC(=O)c1cc(F)c(F)c(Cl)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0840a894e93d4828b9a71ddc2cef0484 | O=C(O)c1c(F)c(F)c(F)c(F)c1F.OCc1ccccc1>>O=C(OCc1ccccc1)c1c(F)c(F)c(F)c(F)c1F | FC1=C(C(=O)O)C(=C(C(=C1F)F)F)F.C(C1=CC=CC=C1)O.Cl.CN(CCCN=C=NCC)C>>C(C1=CC=CC=C1)OC(C1=C(C(=C(C(=C1F)F)F)F)F)=O | O[C:2](=[O:1])[c:11]1[c:12]([F:13])[c:14]([F:15])[c:16]([F:17])[c:18]([F:19])[c:20]1[F:21].[OH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[c:12]([F:13])[c:14]([F:15])[c:16]([F:17])[c:18]([F:19])[c:20]1[F:21] | O=C(O)c1c(F)c(F)c(F)c(F)c1F.OCc1ccccc1 | O=C(OCc1ccccc1)c1c(F)c(F)c(F)c(F)c1F | null | CN(C1=CC=NC=C1)C | ClCCl.[Cl-].[Na+].O | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(OCc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[OH;D1;+0:6]-[C:7]-[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[O;H0;D2;+0:6]-[C:7]-[c:8])-[c:3](:[c:4]):[c:5] | 77.3 | [{"value": 77.3, "product": "C(C1=CC=CC=C1)OC(C1=C(C(=C(C(=C1F)F)F)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | A solution of 2,3,4,5,6-pentafluorobenzoic acid (15.25 g, 71.9 mmol), 4-dimethylaminopyridine (4.4 g, 36.0 mmol) and benzyl alcohol (7.4 mL, 71.5 mmol) in dichloromethane (150 mL) is cooled to 0° C. under an inert atmosphere. 1-[3-(Dimethylamino)propyl]-3-ethyl carbodiimide hydrochloride (16.7 g, 87.1 mmol) is added an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.ClCCl.[Cl-].[Na+].O | 0 | 2 | O=C(O)c1c(F)c(F)c(F)c(F)c1F.OCc1ccccc1>CN(C1=CC=NC=C1)C.ClCCl.[Cl-].[Na+].O>O=C(OCc1ccccc1)c1c(F)c(F)c(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3877a34e25a14eca872308956d9ca54b | CCO.O=C(O)c1cc(F)c(F)cc1F>>CCOC(=O)c1cc(F)c(F)cc1F | FC1=C(C(=O)O)C=C(C(=C1)F)F.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C)OC(C1=C(C=C(C(=C1)F)F)F)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[cH:12][c:13]1[F:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[cH:12][c:13]1[F:14] | CCO.O=C(O)c1cc(F)c(F)cc1F | CCOC(=O)c1cc(F)c(F)cc1F | null | CN(C=O)C | ClCCl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 97.3 | [{"value": 97.3, "product": "C(C)OC(C1=C(C=C(C(=C1)F)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | To a solution of 2,4,5-trifluorobenzoic acid (10.85 g, 61.6 mmol) in dichloromethane (100 mL) is added oxalyl chloride (13.5 mL, 154 mmol) and N,N-dimethylformamide (1 drop). After 45 minutes, the reaction mixture is concentrated under vacuum. The resulting residue is dissolved in dichloromethane (100 mL), and to this ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C=O)C.ClCCl | null | 0.75 | CCO.O=C(O)c1cc(F)c(F)cc1F>CN(C=O)C.ClCCl>CCOC(=O)c1cc(F)c(F)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-773f119220524fabb53ac3ee22baac20 | CCO.COc1c(F)c(F)cc(C(=O)O)c1F>>CCOC(=O)c1cc(F)c(F)c(OC)c1F | C(=O)(O)[O-].[Na+].C(C)O.FC1=C(C(=O)O)C=C(C(=C1OC)F)F.C(C(=O)Cl)(=O)Cl>>C(C)OC(C1=C(C(=C(C(=C1)F)F)OC)F)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]([O:13][CH3:14])[c:15]1[F:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]([O:13][CH3:14])[c:15]1[F:16] | CCO.COc1c(F)c(F)cc(C(=O)O)c1F | CCOC(=O)c1cc(F)c(F)c(OC)c1F | null | CN(C=O)C | ClCCl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 98.8 | [{"value": 98.8, "product": "C(C)OC(C1=C(C(=C(C(=C1)F)F)OC)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | MINUTE | A solution of 2,4,5-trifluoro-3-methoxybenzoic acid (2.513 g, 12.19 mmol) in dichloromethane (50 mL) at 0° C. is treated with oxalyl chloride (5.4 mL, 61.9 mmol) followed by N,N-dimethylformamide (4 drops). The mixture is stirred at 0° C. for 5 minutes and then at room temperature for 2.5 hours. The mixture is concentr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C=O)C.ClCCl | 0 | 0.083333 | CCO.COc1c(F)c(F)cc(C(=O)O)c1F>CN(C=O)C.ClCCl>CCOC(=O)c1cc(F)c(F)c(OC)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1ce2e721306346368ed59e7d64aa7c46 | CCO.O=C(O)c1ccc(F)c(F)c1F>>CCOC(=O)c1ccc(F)c(F)c1F | FC1=C(C(=O)O)C=CC(=C1F)F.C(C(=O)Cl)(=O)Cl.C(C)O>>C(C)OC(C1=C(C(=C(C=C1)F)F)F)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[c:13]1[F:14] | CCO.O=C(O)c1ccc(F)c(F)c1F | CCOC(=O)c1ccc(F)c(F)c1F | null | CN(C=O)C | ClCCl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 97.3 | [{"value": 97.3, "product": "C(C)OC(C1=C(C(=C(C=C1)F)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | To a solution of 2,3,4-trifluorobenzoic acid (10.85 g, 61.6 mmol) in dichloromethane (100 mL) is added oxalyl chloride (13.5 mL, 154 mmol) and N,N-dimethylformamide (3 drops). After 45 minutes, the reaction mixture is concentrated under vacuum. The resulting residue is dissolved in dichloromethane (100 mL) and to this ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C=O)C.ClCCl | null | 0.75 | CCO.O=C(O)c1ccc(F)c(F)c1F>CN(C=O)C.ClCCl>CCOC(=O)c1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-49a5979b87634687b079fe6f0767adec | CCO.COc1cc(C(=O)O)c(F)c(F)c1F>>CCOC(=O)c1cc(OC)c(F)c(F)c1F | C(=O)(O)[O-].[Na+].C(C)O.FC1=C(C(=O)O)C=C(C(=C1F)F)OC.C(C(=O)Cl)(=O)Cl>>C(C)OC(C1=C(C(=C(C(=C1)OC)F)F)F)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][c:8]([O:9][CH3:10])[c:11]([F:12])[c:13]([F:14])[c:15]1[F:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([O:9][CH3:10])[c:11]([F:12])[c:13]([F:14])[c:15]1[F:16] | CCO.COc1cc(C(=O)O)c(F)c(F)c1F | CCOC(=O)c1cc(OC)c(F)c(F)c1F | null | CN(C=O)C | ClCCl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 96.8 | [{"value": 96.8, "product": "C(C)OC(C1=C(C(=C(C(=C1)OC)F)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | A solution of 2,3,4-trifluoro-5-methoxybenzoic acid (Hayashi et al., Bull. Chem. Soc. Jap., 1972; 45(9):2909–2914, 3.443 g, 16.7 mmol) in dichloromethane (100 mL) at 0° C. is treated with oxalyl chloride (7 mL, 80 mmol) followed by N,N-dimethylformamide (4 drops). The mixture is stirred at room temperature for 3.5 hour... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C=O)C.ClCCl | null | 3.5 | CCO.COc1cc(C(=O)O)c(F)c(F)c1F>CN(C=O)C.ClCCl>CCOC(=O)c1cc(OC)c(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-94367b51827344b28aabf8e704d11349 | CCO.Cc1c(F)c(F)cc(C(=O)O)c1F>>CCOC(=O)c1cc(F)c(F)c(C)c1F | C(=O)(O)[O-].[Na+].C(C)O.CC=1C(=C(C(=O)O)C=C(C1F)F)F.C(C(=O)Cl)(=O)Cl>>C(C)OC(C1=C(C(=C(C(=C1)F)F)C)F)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]([CH3:13])[c:14]1[F:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]([CH3:13])[c:14]1[F:15] | CCO.Cc1c(F)c(F)cc(C(=O)O)c1F | CCOC(=O)c1cc(F)c(F)c(C)c1F | null | CN(C=O)C | ClCCl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C;D1;H3:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 77.1 | [{"value": 77.1, "product": "C(C)OC(C1=C(C(=C(C(=C1)F)F)C)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of 3-methyl-2,4,5-trifluorobenzoic acid (Shimizu T., Asai T., Kumai S., Jpn. Kokai Tokkyo Koho (1997) Japanese Appl. JP 95-219069, 4.3 g, 22.6 mmol) in dichloromethane (100 mL) at 0° C. is treated with oxalyl chloride (4.2 g, 33 mmol) followed by N,N-dimethylformamide (2 drops). The mixture is stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | CN(C=O)C.ClCCl | null | 3 | CCO.Cc1c(F)c(F)cc(C(=O)O)c1F>CN(C=O)C.ClCCl>CCOC(=O)c1cc(F)c(F)c(C)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fe4ad7640e624dbfaf995746fd968f26 | NOCc1ccccc1.O=Cc1c(F)c(F)cc(C(=O)O)c1F>>O=C(O)c1cc(F)c(F)c(C=NOCc2ccccc2)c1F | Cl.FC1=C(C(=O)O)C=C(C(=C1C=O)F)F.C(C)N(CC)CC.Cl.C(C1=CC=CC=C1)ON>>C(C1=CC=CC=C1)ON=CC=1C(=C(C(=O)O)C=C(C1F)F)F | [NH2:12][O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.O=[CH:11][c:10]1[c:8]([F:9])[c:6]([F:7])[cH:5][c:4]([C:2](=[O:1])[OH:3])[c:21]1[F:22]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[c:10]([CH:11]=[N:12][O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:21]1[F:22] | NOCc1ccccc1.O=Cc1c(F)c(F)cc(C(=O)O)c1F | O=C(O)c1cc(F)c(F)c(C=NOCc2ccccc2)c1F | null | null | O1CCCC1.[Cl-].[Na+].O | Heteroatom Alkylation and Arylation | OtherReaction | 54882f986dad145756472fc79464161665827db6af7b3780cb2b83c72b495424 | 3d6c7b6a0f29252ce5dcda36fa3ef05efc366c421f47850a88ae430c686fc79d | C(=NOCc1ccccc1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[NH2;D1;+0:7]>>[C:5]-[#8:6]-[N;H0;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 100 | [{"value": 100.0, "product": "C(C1=CC=CC=C1)ON=CC=1C(=C(C(=O)O)C=C(C1F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,4,5-Trifluoro-3-formylbenzoic acid (Horiuchi N., Yonezawa T., Chiba K., Yoshida H., PCT Int. Appl. [1999] WO 97-JP2918), (5.70 g, 27.9 mmol), triethylamine (11 mL, 78.9 mmol), O-benzylhydroxylamine hydrochloride (4.47 g, 28.0 mmol) and anhydrous tetrahydrofuran (150 mL) are stirred at room temperature for 50 hours. T... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | null | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCCC1.[Cl-].[Na+].O | null | null | NOCc1ccccc1.O=Cc1c(F)c(F)cc(C(=O)O)c1F>O1CCCC1.[Cl-].[Na+].O>O=C(O)c1cc(F)c(F)c(C=NOCc2ccccc2)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-86eb074600d544ca8411b5312724ec9d | CCO.O=C(O)c1cc(F)c(F)c(C=NOCc2ccccc2)c1F>>CCOC(=O)c1cc(F)c(F)c(C=NOCc2ccccc2)c1F | C(C1=CC=CC=C1)ON=CC=1C(=C(C(=O)O)C=C(C1F)F)F.C(C)O.Cl.C(C)N=C=NCCCN(C)C>>C(C)OC(C1=C(C(=C(C(=C1)F)F)C=NOCC1=CC=CC=C1)F)=O | O[CH2:2][CH3:1].[OH:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]([CH:13]=[N:14][O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]1[F:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]([CH:13]=[N:14][O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:2... | CCO.O=C(O)c1cc(F)c(F)c(C=NOCc2ccccc2)c1F | CCOC(=O)c1cc(F)c(F)c(C=NOCc2ccccc2)c1F | null | CN(C1=CC=NC=C1)C | ClCCl | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 3f9a9ace480b666da05fcfe5450d12b5c1ea5b0d435c195e1dd4bd20281604bb | dcbf04ec563ed0e9dfc79070490a028958024079a671c385858bb18cc8ec995a | C(=NOCc1ccccc1)c1ccccc1 | O-[CH2;D2;+0:1]-[C;D1;H3:2].[O;D1;H0:3]=[C:4](-[OH;D1;+0:5])-[c:6]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[C:4](=[O;D1;H0:3])-[c:6] | 53.3 | [{"value": 53.3, "product": "C(C)OC(C1=C(C(=C(C(=C1)F)F)C=NOCC1=CC=CC=C1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | 3-(Benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acid (0.117 g, 0.378 mmol), 4-dimethylaminopyridine (0.023 g, 0.189 mmol), anhydrous ethanol (0.030 mL, 0.517 mmol) are mixed in dichloromethane (6 mL), cooled to 0° C., and treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.082 g, 0.427 mmol). Af... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.ClCCl | 0 | 2 | CCO.O=C(O)c1cc(F)c(F)c(C=NOCc2ccccc2)c1F>CN(C1=CC=NC=C1)C.ClCCl>CCOC(=O)c1cc(F)c(F)c(C=NOCc2ccccc2)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5cc3631dde2a4f1db31e448dc5290720 | CC(C)(C)OC(=O)N[C@H]1CCNC1.CCOC(=O)c1cc(F)c(F)c(F)c1F>>CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1F | C(C)OC(C1=C(C(=C(C(=C1)F)F)F)F)=O.C(C)(C)(C)OC(N[C@@H]1CNCC1)=O.C(C)N(CC)CC>>C(C)OC(C1=C(C(=C(C(=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)F)=O | [NH:11]1[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]1.F[c:10]1[c:8]([F:9])[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:26]([F:27])[c:24]1[F:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([N:11]2[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[O:17])[O:... | CC(C)(C)OC(=O)N[C@H]1CCNC1.CCOC(=O)c1cc(F)c(F)c(F)c1F | CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1F | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]1-[C:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[F;D1;H0:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:8]-[C:9]-[C:10]-[C:11]-1):[c:5](-[F;D1;H0:6]):[c:7] | 74.5 | [{"value": 74.5, "product": "C(C)OC(C1=C(C(=C(C(=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,3,4,5-tetrafluorobenzoic acid ethyl ester (Example 1a, 4.03 g, 18.1 mmol), (S)-pyrrolidin-3-ylcarbamic acid tert-butyl ester (4.02 g, 21.6 mmol) (Sanchez J. P., Domagala J. M., Heifetz C. L., Priebe S. R., Sesnie J. A., Trehan A. K., J. Med. Chem., 1992; 35(10):1764–1773), and triethylamine (18.0 mL, 12... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | c1ccccc1.C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HF | C(C)#N | null | null | CC(C)(C)OC(=O)N[C@H]1CCNC1.CCOC(=O)c1cc(F)c(F)c(F)c1F>C(C)#N>CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-acbacd71398448cdac9007290ea3a3a2 | CC(C)(C)OC(=O)N[C@H]1CCNC1.CCOC(=O)c1c(F)cc(F)c(F)c1F>>CCOC(=O)c1c(F)cc(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1F | C(C)OC(C1=C(C(=C(C=C1F)F)F)F)=O.C(C)N(CC)CC.C(C)(C)(C)OC(N[C@@H]1CNCC1)=O>>C(C)OC(C1=C(C(=C(C=C1F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)F)=O | [NH:11]1[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]1.F[c:10]1[cH:9][c:7]([F:8])[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:26]([F:27])[c:24]1[F:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([F:8])[cH:9][c:10]([N:11]2[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[O:17])[O:... | CC(C)(C)OC(=O)N[C@H]1CCNC1.CCOC(=O)c1c(F)cc(F)c(F)c1F | CCOC(=O)c1c(F)cc(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1F | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:7]-[C:8]-[C:9]-[C:10]-1):[c:2]:[c:3] | 69.8 | [{"value": 69.8, "product": "C(C)OC(C1=C(C(=C(C=C1F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,3,4,6-tetrafluorobenzoic acid ethyl ester (Example 1b, 5.1 g, 22.9 mmol), triethylamine (22 mL, 157 mmol), and (S)-pyrrolidin-3-ylcarbamic acid tert-butyl ester (5.2 g, 27.9 mmol) in acetonitrile (60 mL) is stirred at room temperature for 64 hours. The mixture is concentrated in vacuo and the residue di... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | c1ccccc1.C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HF | C(C)#N | null | null | CC(C)(C)OC(=O)N[C@H]1CCNC1.CCOC(=O)c1c(F)cc(F)c(F)c1F>C(C)#N>CCOC(=O)c1c(F)cc(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2dd800356e8c4c8d8b56e82b571f1f7f | CC(C)(C)OC(=O)N[C@H]1CCNC1.CCOC(=O)c1cc(F)c(F)c(Cl)c1F>>CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1F | C(C)OC(C1=C(C(=C(C(=C1)F)F)Cl)F)=O.C(C)N(CC)CC.C(C)(C)(C)OC(N[C@@H]1CNCC1)=O>>C(C)OC(C1=C(C(=C(C(=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)Cl)F)=O | [NH:11]1[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]1.F[c:10]1[c:8]([F:9])[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:26]([F:27])[c:24]1[Cl:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([N:11]2[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[O:17])[O... | CC(C)(C)OC(=O)N[C@H]1CCNC1.CCOC(=O)c1cc(F)c(F)c(Cl)c1F | CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1F | null | null | C(C)(=O)OCC.C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[Cl;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]1-[C:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[Cl;D1;H0:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:8]-[C:9]-[C:10]-[C:11]-1):[c:5](-[F;D1;H0:6]):[c:7] | 100.1 | [{"value": 100.1, "product": "C(C)OC(C1=C(C(=C(C(=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)Cl)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | To a solution of 3-chloro-2,4,5-trifluorobenzoic acid ethyl ester (Example 1c, 5.50 g, 23.05 mmol) in acetonitrile (25 mL) is added triethylamine (6.43 mL, 46.1 mmol) and (S)-pyrrolidin-3-ylcarbamic acid tert-butyl ester (4.72 g, 25.4 mmol). After 48 hours, the mixture is diluted with ethyl acetate and washed with satu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | c1ccccc1.C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HF | C(C)(=O)OCC.C(C)#N | null | 48 | CC(C)(C)OC(=O)N[C@H]1CCNC1.CCOC(=O)c1cc(F)c(F)c(Cl)c1F>C(C)(=O)OCC.C(C)#N>CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0359e6b7f9d248c590d7dedd48f39951 | CC(C)(C)OC(=O)N[C@H]1CCNC1.O=C(OCc1ccccc1)c1c(F)c(F)c(F)c(F)c1F>>CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(F)c(C(=O)OCc3ccccc3)c(F)c2F)C1 | C(C1=CC=CC=C1)OC(C1=C(C(=C(C(=C1F)F)F)F)F)=O.C(C)N(CC)CC.C(C)(C)(C)OC(N[C@@H]1CNCC1)=O>>C(C1=CC=CC=C1)OC(C1=C(C(=C(C(=C1F)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)F)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][NH:12][CH2:33]1.F[c:13]1[c:14]([F:15])[c:16]([F:17])[c:18]([C:19](=[O:20])[O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:29]([F:30])[c:31]1[F:32]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][N... | CC(C)(C)OC(=O)N[C@H]1CCNC1.O=C(OCc1ccccc1)c1c(F)c(F)c(F)c(F)c1F | CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(F)c(C(=O)OCc3ccccc3)c(F)c2F)C1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(OCc1ccccc1)c1ccc(N2CCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]1-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[F;D1;H0:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:12]-[C:11]-1):[c:5](-[F;D1;H0:6]):[c:7] | 63.6 | [{"value": 63.6, "product": "C(C1=CC=CC=C1)OC(C1=C(C(=C(C(=C1F)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,3,4,5,6-pentafluorobenzoic acid benzyl ester (Example 1d, 8.05 g, 26.6 mmol), triethylamine (26 mL, 186 mmol), and (S)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (5.6 g, 30 mmol) in acetonitrile (150 mL) is stirred at room temperature for 24 hours. The solvent is removed under vacuum and the residue... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccccc1 | HF | C(C)#N | null | null | CC(C)(C)OC(=O)N[C@H]1CCNC1.O=C(OCc1ccccc1)c1c(F)c(F)c(F)c(F)c1F>C(C)#N>CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(F)c(C(=O)OCc3ccccc3)c(F)c2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1240102ce85149d2a6f45262f5dded3b | C1CCNC1.CCOC(=O)c1cc(F)c(F)cc1F>>CCOC(=O)c1cc(F)c(N2CCCC2)cc1F | C(C)OC(C1=C(C=C(C(=C1)F)F)F)=O.C(C)N(CC)CC.N1CCCC1>>C(C)OC(C1=C(C=C(C(=C1)F)N1CCCC1)F)=O | [NH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1.F[c:10]1[c:8]([F:9])[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:17]([F:18])[cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([N:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[cH:16][c:17]1[F:18] | C1CCNC1.CCOC(=O)c1cc(F)c(F)cc1F | CCOC(=O)c1cc(F)c(N2CCCC2)cc1F | null | null | C(C)(=O)OCC.C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:7]-[C:8]-[C:9]-[C:10]-1):[c:2]:[c:3] | 97 | [{"value": 97.0, "product": "C(C)OC(C1=C(C=C(C(=C1)F)N1CCCC1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 2,4,5-trifluorobenzoic acid ethyl ester (Example 1e, 4.32 g, 21.2 mmol) in acetonitrile (25 mL) is added triethylamine (5.9 mL, 42.3 mmol) and pyrrolidine (2.2 mL, 25.4 mmol). After 24 hours, the reaction mixture is diluted with ethyl acetate and washed with saturated NaHCO3, water, and brine. The orga... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | c1ccccc1.C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HF | C(C)(=O)OCC.C(C)#N | null | 24 | C1CCNC1.CCOC(=O)c1cc(F)c(F)cc1F>C(C)(=O)OCC.C(C)#N>CCOC(=O)c1cc(F)c(N2CCCC2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f2ce1d24c4af410d90ca4f96147cdb48 | CC(C)(C)OC(=O)NC1CCNC1.CCOC(=O)c1cc(F)c(F)c(OC)c1F>>CCOC(=O)c1cc(F)c(N2CCC(NC(=O)OC(C)(C)C)C2)c(OC)c1F | C(C)OC(C1=C(C(=C(C(=C1)F)F)OC)F)=O.C(C)(C)(C)OC(NC1CNCC1)=O.C(C)N(CC)CC>>C(C)OC(C1=C(C(=C(C(=C1)F)N1CC(CC1)NC(=O)OC(C)(C)C)OC)F)=O | [NH:11]1[CH2:12][CH2:13][CH:14]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]1.F[c:10]1[c:8]([F:9])[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:27]([F:28])[c:24]1[O:25][CH3:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([N:11]2[CH2:12][CH2:13][CH:14]([NH:15][C:16](=[O:1... | CC(C)(C)OC(=O)NC1CCNC1.CCOC(=O)c1cc(F)c(F)c(OC)c1F | CCOC(=O)c1cc(F)c(N2CCC(NC(=O)OC(C)(C)C)C2)c(OC)c1F | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[#8:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]1-[C:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[#8:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:8]-[C:9]-[C:10]-[C:11]-1):[c:5](-[F;D1;H0:6]):[c:7] | 77.6 | [{"value": 77.6, "product": "C(C)OC(C1=C(C(=C(C(=C1)F)N1CC(CC1)NC(=O)OC(C)(C)C)OC)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,4,5-trifluoro-3-methoxybenzoic acid ethyl ester (Example 1f, 2.821 g, 12.05 mmol), pyrrolidin-3-ylcarbamic acid tert-butyl ester (3.310 g, 17.77 mmol), and triethylamine (9.13 g, 12.6 mL, 90.23 mmol) in acetonitrile (50 mL) is heated at 40° C. under nitrogen for 2 days. The yellow solution is concentrat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | c1ccccc1.C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HF | C(C)#N | null | null | CC(C)(C)OC(=O)NC1CCNC1.CCOC(=O)c1cc(F)c(F)c(OC)c1F>C(C)#N>CCOC(=O)c1cc(F)c(N2CCC(NC(=O)OC(C)(C)C)C2)c(OC)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-61d96d89dc3346d09c856b21814d1a9f | CC(C)(C)OC(=O)NC1CCNC1.CCOC(=O)c1cc(F)c(F)c(Cl)c1F>>CCOC(=O)c1cc(F)c(N2CCC(NC(=O)OC(C)(C)C)C2)c(Cl)c1F | C(C)OC(C1=C(C(=C(C(=C1)F)F)Cl)F)=O.C(C)N(CC)CC.C(C)(C)(C)OC(NC1CNCC1)=O>>C(C)OC(C1=C(C(=C(C(=C1)F)N1CC(CC1)NC(=O)OC(C)(C)C)Cl)F)=O | [NH:11]1[CH2:12][CH2:13][CH:14]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]1.F[c:10]1[c:8]([F:9])[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:26]([F:27])[c:24]1[Cl:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([N:11]2[CH2:12][CH2:13][CH:14]([NH:15][C:16](=[O:17])[O:1... | CC(C)(C)OC(=O)NC1CCNC1.CCOC(=O)c1cc(F)c(F)c(Cl)c1F | CCOC(=O)c1cc(F)c(N2CCC(NC(=O)OC(C)(C)C)C2)c(Cl)c1F | null | null | C(C)(=O)OCC.C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[Cl;D1;H0:3]):[c:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]1-[C:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[Cl;D1;H0:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:8]-[C:9]-[C:10]-[C:11]-1):[c:5](-[F;D1;H0:6]):[c:7] | 98.6 | [{"value": 98.6, "product": "C(C)OC(C1=C(C(=C(C(=C1)F)N1CC(CC1)NC(=O)OC(C)(C)C)Cl)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | To a solution of 3-chloro-2,4,5-tri-fluorobenzoic acid ethyl ester (Example 1c, 5.50 g, 23.05 mmol) in acetonitrile (25 mL) is added triethylamine (6.43 mL, 46.1 mmol) and pyrrolidin-3-ylcarbamic acid tert-butyl ester (4.72 g, 25.4 mmol). After 48 hours, the mixture is diluted with ethyl acetate and washed with saturat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | c1ccccc1.C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HF | C(C)(=O)OCC.C(C)#N | null | 48 | CC(C)(C)OC(=O)NC1CCNC1.CCOC(=O)c1cc(F)c(F)c(Cl)c1F>C(C)(=O)OCC.C(C)#N>CCOC(=O)c1cc(F)c(N2CCC(NC(=O)OC(C)(C)C)C2)c(Cl)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4cd038f4ec2c4063a2e06a388d2c39ee | CC(C)(C)OC(=O)NC1CCNC1.CCOC(=O)c1ccc(F)c(F)c1F>>CCOC(=O)c1ccc(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1F | C(C)OC(C1=C(C(=C(C=C1)F)F)F)=O.C(C)(C)(C)OC(NC1CNCC1)=O.C(C)N(CC)CC>>C(C)OC(C1=C(C(=C(C=C1)N1CC(CC1)NC(=O)OC(C)(C)C)F)F)=O | [NH:10]1[CH2:11][CH2:12][CH:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22]1.F[c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:25]([F:26])[c:23]1[F:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][CH:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:1... | CC(C)(C)OC(=O)NC1CCNC1.CCOC(=O)c1ccc(F)c(F)c1F | CCOC(=O)c1ccc(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1F | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:7]-[C:8]-[C:9]-[C:10]-1):[c:2]:[c:3] | 70.1 | [{"value": 70.1, "product": "C(C)OC(C1=C(C(=C(C=C1)N1CC(CC1)NC(=O)OC(C)(C)C)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,3,4-trifluorobenzoic acid ethyl ester (Example 1g, 3.70 g, 18.1 mmol), pyrrolidin-3-ylcarbamic acid tert-butyl ester (4.02 g, 21.6 mmol), and triethylamine (18.0 mL, 129 mmol) in acetonitrile (50 mL) is heated at 50° C. under nitrogen atmosphere for 4.5 hours. The solution is concentrated in vacuo and p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | c1ccccc1.C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HF | C(C)#N | null | null | CC(C)(C)OC(=O)NC1CCNC1.CCOC(=O)c1ccc(F)c(F)c1F>C(C)#N>CCOC(=O)c1ccc(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0a282666be1a4e63bfa975c0f623bbd3 | CC(C)(C)OC(=O)NC1CCNC1.CCOC(=O)c1cc(F)c(F)cc1F>>CCOC(=O)c1cc(F)c(N2CCC(NC(=O)OC(C)(C)C)C2)cc1F | C(C)OC(C1=C(C=C(C(=C1)F)F)F)=O.C(C)N(CC)CC.C(C)(C)(C)OC(NC1CNCC1)=O>>C(C)OC(C1=C(C=C(C(=C1)F)N1CC(CC1)NC(=O)OC(C)(C)C)F)=O | [NH:11]1[CH2:12][CH2:13][CH:14]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]1.F[c:10]1[c:8]([F:9])[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:25]([F:26])[cH:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([N:11]2[CH2:12][CH2:13][CH:14]([NH:15][C:16](=[O:17])[O:18][C:1... | CC(C)(C)OC(=O)NC1CCNC1.CCOC(=O)c1cc(F)c(F)cc1F | CCOC(=O)c1cc(F)c(N2CCC(NC(=O)OC(C)(C)C)C2)cc1F | null | null | C(C)(=O)OCC.C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:7]-[C:8]-[C:9]-[C:10]-1):[c:2]:[c:3] | null | [] | null | null | 45 | HOUR | To a solution of 2,4,5-trifluorobenzoic acid ethyl ester (Example 1e, 14.8 g, 72.4 mmol) in acetonitrile (225 mL) is added triethylamine (65 mL, 466 mmol) and pyrrolidin-3-ylcarbamic acid tert-butyl ester (16.07 g, 86.2 mmol). After 45 hours, the reaction mixture is diluted with ethyl acetate and washed with saturated ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | c1ccccc1.C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HF | C(C)(=O)OCC.C(C)#N | null | 45 | CC(C)(C)OC(=O)NC1CCNC1.CCOC(=O)c1cc(F)c(F)cc1F>C(C)(=O)OCC.C(C)#N>CCOC(=O)c1cc(F)c(N2CCC(NC(=O)OC(C)(C)C)C2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0390ee46401f4971ae2800d3e2994491 | CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1F.NC1CC1>>CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1 | C(C)OC(C1=C(C(=C(C(=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)F)=O.C1(CC1)N>>C(C)OC(C1=C(C(=C(C(=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)NC1CC1)=O | F[c:26]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][c:8]([F:9])[c:10]([N:11]2[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]2)[c:24]1[F:25].[NH2:27][CH:28]1[CH2:29][CH2:30]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([N:11]2[CH2:12][CH2:13][C@H:14]... | CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1F.NC1CC1 | CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(NC2CC2)cc(N2CCCC2)c1 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]):[c:10].[NH2;D1;+0:11]-[C:12]1-[C:13]-[C:14]-1>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c:5](:[c:10]):[c;H0;D3;+0:1](-[NH;D2;+0:11]-[C:12]1-[C:13]-[C:14]-1):[c:2](-[F;D1;H0:3]):[c:4] | 83 | [{"value": 83.0, "product": "C(C)OC(C1=C(C(=C(C(=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)NC1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-[(S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-2,3,5-trifluorobenzoic acid ethyl ester (Example 2a, 1.95 g, 5.01 mmol) and cyclopropylamine (14.0 mL, 201 mmol) in dimethyl sulfoxide (5 mL) is heated in a sealed glass tube for 44.5 hours at 100° C. Compressed air is blown into the black solution to re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]C1.C1CC1 | HF | CS(=O)C | null | null | CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1F.NC1CC1>CS(=O)C>CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-57255046f53942d386f59bb285a97248 | CCOC(=O)c1c(F)cc(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1F.NC1CC1>>CCOC(=O)c1c(F)cc(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1 | C(C)OC(C1=C(C(=C(C=C1F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)F)=O.C1(CC1)N>>C(C)OC(C1=C(C(=C(C=C1F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)NC1CC1)=O | F[c:26]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:7]([F:8])[cH:9][c:10]([N:11]2[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]2)[c:24]1[F:25].[NH2:27][CH:28]1[CH2:29][CH2:30]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([F:8])[cH:9][c:10]([N:11]2[CH2:12][CH2:13][C@H:14]... | CCOC(=O)c1c(F)cc(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1F.NC1CC1 | CCOC(=O)c1c(F)cc(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(NC2CC2)cc(N2CCCC2)c1 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]):[c:10].[NH2;D1;+0:11]-[C:12]1-[C:13]-[C:14]-1>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c:5](:[c:10]):[c;H0;D3;+0:1](-[NH;D2;+0:11]-[C:12]1-[C:13]-[C:14]-1):[c:2](-[F;D1;H0:3]):[c:4] | 81.2 | [{"value": 81.2, "product": "C(C)OC(C1=C(C(=C(C=C1F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)NC1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-[(S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-2,3,6-trifluorobenzoic acid ethyl ester (Example 2b, 5.4 g, 13.9 mmol), cyclopropylamine (40 mL, 577 mmol), and dimethyl sulfoxide (28 mL) in a sealed glass tube is heated at 100° C. for 27 hours. The excess amine is removed by blowing in compressed air ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]C1.C1CC1 | HF | CS(=O)C | null | null | CCOC(=O)c1c(F)cc(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1F.NC1CC1>CS(=O)C>CCOC(=O)c1c(F)cc(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-17cd02a021354dd183a83816d55b9074 | CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1F.NC1CC1>>CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1NC1CC1 | C(C)OC(C1=C(C(=C(C(=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)Cl)F)=O.C1(CC1)N.CS(=O)C>>C(C)OC(C1=C(C(=C(C(=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)Cl)NC1CC1)=O | F[c:26]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][c:8]([F:9])[c:10]([N:11]2[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]2)[c:24]1[Cl:25].[NH2:27][CH:28]1[CH2:29][CH2:30]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([N:11]2[CH2:12][CH2:13][C@H:14... | CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1F.NC1CC1 | CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1NC1CC1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(NC2CC2)cc(N2CCCC2)c1 | F-[c;H0;D3;+0:1](:[c:2](-[Cl;D1;H0:3]):[c:4]):[c:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]):[c:10].[NH2;D1;+0:11]-[C:12]1-[C:13]-[C:14]-1>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c:5](:[c:10]):[c;H0;D3;+0:1](-[NH;D2;+0:11]-[C:12]1-[C:13]-[C:14]-1):[c:2](-[Cl;D1;H0:3]):[c:4] | 43.2 | [{"value": 43.2, "product": "C(C)OC(C1=C(C(=C(C(=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)Cl)NC1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-[(S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-3-chloro-2,5-difluorobenzoic acid ethyl ester (Example 2c, 9.34 g, 23.1 mmol), cyclopropylamine (16 mL, 228 mmol), and dimethyl sulfoxide (30 mL) is heated in a sealed tube at 110° C. for 3 days. After cooling to room temperature, the reaction mixture is... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]C1.C1CC1 | HF | C(C)(=O)OCC | null | null | CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1F.NC1CC1>C(C)(=O)OCC>CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1NC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bafe96c800354c5393ce9d00526fb0c7 | CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(F)c(C(=O)OCc3ccccc3)c(F)c2F)C1.NC1CC1>>CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(F)c(C(=O)OCc3ccccc3)c(NC3CC3)c2F)C1 | C(C1=CC=CC=C1)OC(C1=C(C(=C(C(=C1F)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)F)=O.C1(CC1)N>>C(C1=CC=CC=C1)OC(C1=C(C(=C(C(=C1F)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)NC1CC1)=O | F[c:29]1[c:18]([C:19](=[O:20])[O:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:16]([F:17])[c:14]([F:15])[c:13]([N:12]2[CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:36]2)[c:34]1[F:35].[NH2:30][CH:31]1[CH2:32][CH2:33]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:... | CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(F)c(C(=O)OCc3ccccc3)c(F)c2F)C1.NC1CC1 | CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(F)c(C(=O)OCc3ccccc3)c(NC3CC3)c2F)C1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(OCc1ccccc1)c1ccc(N2CCCC2)cc1NC1CC1 | F-[c;H0;D3;+0:1](:[c:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6]):[c:7]):[c:8](-[F;D1;H0:9]):[c:10].[NH2;D1;+0:11]-[C:12]1-[C:13]-[C:14]-1>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[c:2](:[c:7]):[c;H0;D3;+0:1](-[NH;D2;+0:11]-[C:12]1-[C:13]-[C:14]-1):[c:8](-[F;D1;H0:9]):[c:10] | 86.2 | [{"value": 86.2, "product": "C(C1=CC=CC=C1)OC(C1=C(C(=C(C(=C1F)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)NC1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-[(S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-2,3,5,6-tetrafluorobenzoic acid benzyl ester (Example 2d, 2.5 g, 5.3 mmol), cyclopropylamine (40 mL, 577 mmol), and dimethyl sulfoxide (20 mL) in a sealed glass tube is heated at 80° C. for 24 hours. The excess amine is removed by blowing in compressed a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1ccccc1.C1CC1 | HF | CS(=O)C | null | null | CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(F)c(C(=O)OCc3ccccc3)c(F)c2F)C1.NC1CC1>CS(=O)C>CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(F)c(C(=O)OCc3ccccc3)c(NC3CC3)c2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f10a2f09cda54566ab1f1c06aa827088 | CC(C)N.CCOC(=O)c1cc(F)c(N2CCC(NC(=O)OC(C)(C)C)C2)cc1F>>CCOC(=O)c1cc(F)c(N2CCC(NC(=O)OC(C)(C)C)C2)cc1NC(C)C | C(C)OC(C1=C(C=C(C(=C1)F)N1CC(CC1)NC(=O)OC(C)(C)C)F)=O.C(C)(C)N>>C(C)OC(C1=C(C=C(C(=C1)F)N1CC(CC1)NC(=O)OC(C)(C)C)NC(C)C)=O | [NH2:26][CH:27]([CH3:28])[CH3:29].F[c:25]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][c:8]([F:9])[c:10]([N:11]2[CH2:12][CH2:13][CH:14]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]2)[cH:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([N:11]2[CH2:12][CH2:13][CH:14]([NH:15... | CC(C)N.CCOC(=O)c1cc(F)c(N2CCC(NC(=O)OC(C)(C)C)C2)cc1F | CCOC(=O)c1cc(F)c(N2CCC(NC(=O)OC(C)(C)C)C2)cc1NC(C)C | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(N2CCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8]):[c:9].[C;D1;H3:10]-[C:11](-[C;D1;H3:12])-[NH2;D1;+0:13]>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:13]-[C:11](-[C;D1;H3:10])-[C;D1;H3:12]):[c:2]:[c:3] | 28.1 | [{"value": 28.1, "product": "C(C)OC(C1=C(C=C(C(=C1)F)N1CC(CC1)NC(=O)OC(C)(C)C)NC(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-[3-(tert-Butoxycarbonylamino)-pyrrolidin-1-yl]-2,5-difluorobenzoic acid ethyl ester (Example 2j, 5.4 g, 13.9 mmol), isopropylamine (40 mL, 469 mmol), and dimethyl sulfoxide (25 mL) are heated at 100° C. for 4 days in a sealed glass tube. The excess amine is removed by blowing in compressed air. The residue is filtere... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]C1 | HF | CS(=O)C | null | null | CC(C)N.CCOC(=O)c1cc(F)c(N2CCC(NC(=O)OC(C)(C)C)C2)cc1F>CS(=O)C>CCOC(=O)c1cc(F)c(N2CCC(NC(=O)OC(C)(C)C)C2)cc1NC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c9ad7ba81a844b13b2fa7d7f9fd4ed34 | CCC(C)N.CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1F>>CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1NC(C)CC | C(C)OC(C1=C(C(=C(C(=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)Cl)F)=O.C(C)(CC)N>>C(C)OC(C1=C(C(=C(C(=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)Cl)NC(C)CC)=O | [NH2:27][CH:28]([CH3:29])[CH2:30][CH3:31].F[c:26]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][c:8]([F:9])[c:10]([N:11]2[CH2:12][CH2:13][C@H:14]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]2)[c:24]1[Cl:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([N:11]2[CH2:12][CH2:13... | CCC(C)N.CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1F | CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1NC(C)CC | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(N2CCCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[Cl;D1;H0:3]):[c:4]):[c:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]):[c:10].[C:11]-[C:12](-[C;D1;H3:13])-[NH2;D1;+0:14]>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c:5](:[c:10]):[c;H0;D3;+0:1](-[NH;D2;+0:14]-[C:12](-[C:11])-[C;D1;H3:13]):[c:2](-[Cl;D1;H0:3]):[c:4] | 167.5 | [{"value": 167.5, "product": "C(C)OC(C1=C(C(=C(C(=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)Cl)NC(C)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-[(S)-3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-3-chloro-2,5-difluorobenzoic acid ethyl ester (Example 2c, 1.95 g, 4.81 mmol), sec-butylamine (30 mL, 296 mmol), and dimethyl sulfoxide (20 mL) are heated in a sealed glass tube at 110° C. for 24 hours. The reaction mixture is evaporated, and purification by column ch... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]C1 | HF | CS(=O)C | null | null | CCC(C)N.CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1F>CS(=O)C>CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1NC(C)CC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c69cc9c8887b40f49bc3a26eadc7f8aa | CCOC(=O)c1ccc(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1F.NC1CC1>>CCOC(=O)c1ccc(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1 | C(C)OC(C1=C(C(=C(C=C1)N1CC(CC1)NC(=O)OC(C)(C)C)F)F)=O.C1(CC1)N>>C(C)OC(C1=C(C(=C(C=C1)N1CC(CC1)NC(=O)OC(C)(C)C)F)NC1CC1)=O | F[c:25]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][CH:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22]2)[c:23]1[F:24].[NH2:26][CH:27]1[CH2:28][CH2:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][CH:13]([NH:14][C:15](=... | CCOC(=O)c1ccc(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1F.NC1CC1 | CCOC(=O)c1ccc(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1 | null | null | CN(C(C)=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(NC2CC2)cc(N2CCCC2)c1 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]):[c:10].[NH2;D1;+0:11]-[C:12]1-[C:13]-[C:14]-1>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c:5](:[c:10]):[c;H0;D3;+0:1](-[NH;D2;+0:11]-[C:12]1-[C:13]-[C:14]-1):[c:2](-[F;D1;H0:3]):[c:4] | 76.9 | [{"value": 76.9, "product": "C(C)OC(C1=C(C(=C(C=C1)N1CC(CC1)NC(=O)OC(C)(C)C)F)NC1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-[3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-2,3-difluorobenzoic acid ethyl ester (Example 2h, 1.85 g, 5.01 mmol) and cyclopropylamine (14.0 mL, 201 mmol) in N,N-dimethylacetamide (5 mL) is heated in a sealed glass tube for 48 hours at 100° C. The solution is then concentrated under high vacuum and pur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]C1.C1CC1 | HF | CN(C(C)=O)C | null | null | CCOC(=O)c1ccc(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1F.NC1CC1>CN(C(C)=O)C>CCOC(=O)c1ccc(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-04ac14ea81ab4703950b7e11ba716028 | CCOC(=O)c1cc(Cl)c(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1F.NC1CC1>>CCOC(=O)c1cc(Cl)c(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1 | C(C)OC(C1=C(C(=C(C(=C1)Cl)N1CC(CC1)NC(=O)OC(C)(C)C)F)F)=O.C1(CC1)N>>C(C)OC(C1=C(C(=C(C(=C1)Cl)N1CC(CC1)NC(=O)OC(C)(C)C)F)NC1CC1)=O | F[c:26]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][c:8]([Cl:9])[c:10]([N:11]2[CH2:12][CH2:13][CH:14]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23]2)[c:24]1[F:25].[NH2:27][CH:28]1[CH2:29][CH2:30]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([Cl:9])[c:10]([N:11]2[CH2:12][CH2:13][CH:14]... | CCOC(=O)c1cc(Cl)c(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1F.NC1CC1 | CCOC(=O)c1cc(Cl)c(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1 | null | null | CN(C(C)=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(NC2CC2)cc(N2CCCC2)c1 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]):[c:10].[NH2;D1;+0:11]-[C:12]1-[C:13]-[C:14]-1>>[C:9]-[#8:8]-[C:6](=[O;D1;H0:7])-[c:5](:[c:10]):[c;H0;D3;+0:1](-[NH;D2;+0:11]-[C:12]1-[C:13]-[C:14]-1):[c:2](-[F;D1;H0:3]):[c:4] | 48.7 | [{"value": 48.7, "product": "C(C)OC(C1=C(C(=C(C(=C1)Cl)N1CC(CC1)NC(=O)OC(C)(C)C)F)NC1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-[3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-5-chloro-2,3-difluorobenzoic acid ethyl ester (Example 21, 3.75 g, 9.3 mmol) and cyclopropylamine (14.0 mL, 201 mmol) in N,N-dimethylacetamide (5 mL) is heated in a sealed glass tube for 48 hours at 100° C. The solution is then concentrated under high vacuum... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]C1.C1CC1 | HF | CN(C(C)=O)C | null | null | CCOC(=O)c1cc(Cl)c(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1F.NC1CC1>CN(C(C)=O)C>CCOC(=O)c1cc(Cl)c(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ad384940417e4d18b0bae0170e802d31 | CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1NC1CC1>>CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)cc(C(=O)O)c(NC3CC3)c2Cl)C1 | C(C)OC(C1=C(C(=C(C(=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)Cl)NC1CC1)=O.[OH-].[Na+]>>C(C)(C)(C)OC(=O)N[C@@H]1CN(CC1)C1=C(C(=C(C(=O)O)C=C1F)NC1CC1)Cl | CC[O:20][C:18]([c:17]1[cH:16][c:14]([F:15])[c:13]([N:12]2[CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:28]2)[c:26]([Cl:27])[c:21]1[NH:22][CH:23]1[CH2:24][CH2:25]1)=[O:19]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][N:12]([c:13]2[c:14]([F:15])[cH:... | CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1NC1CC1 | CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)cc(C(=O)O)c(NC3CC3)c2Cl)C1 | null | null | CO.C(C)(=O)OCC.O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cc(NC2CC2)cc(N2CCCC2)c1 | C-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 | [] | 80 | CELSIUS | 20 | HOUR | To a solution of 4-[(S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-3-chloro-2-cyclopropylamino-5-fluorobenzoic acid ethyl ester (Example 3c, 2.90 g, 6.56 mmol) in methanol (30 mL) and tetrahydrofuran (30 mL) is added a 1N solution of sodium hydroxide (50 mL). The reaction mixture is stirred at 80° C. for 20 hours, co... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]C1.c1ccccc1.C1CC1 | Other | CO.C(C)(=O)OCC.O1CCCC1 | 80 | 20 | CCOC(=O)c1cc(F)c(N2CC[C@H](NC(=O)OC(C)(C)C)C2)c(Cl)c1NC1CC1>CO.C(C)(=O)OCC.O1CCCC1>CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)cc(C(=O)O)c(NC3CC3)c2Cl)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce8ce431edd04053a879283a27982b23 | CCOC(=O)c1cc(F)c(N2CCCC2)cc1NC1CC1>>O=C(O)c1cc(F)c(N2CCCC2)cc1NC1CC1 | C(C)OC(C1=C(C=C(C(=C1)F)N1CCCC1)NC1CC1)=O.[OH-].[Na+]>>C1(CC1)NC1=C(C(=O)O)C=C(C(=C1)N1CCCC1)F | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][c:6]([F:7])[c:8]([N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][c:15]1[NH:16][CH:17]1[CH2:18][CH2:19]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][c:15]1[NH:16][CH:17]1[CH2:18][CH2:19]1 | CCOC(=O)c1cc(F)c(N2CCCC2)cc1NC1CC1 | O=C(O)c1cc(F)c(N2CCCC2)cc1NC1CC1 | null | null | CO.C(C)(=O)OCC.O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cc(NC2CC2)cc(N2CCCC2)c1 | C-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] | 89.9 | [{"value": 89.9, "product": "C1(CC1)NC1=C(C(=O)O)C=C(C(=C1)N1CCCC1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 20 | HOUR | To a solution of 4-(pyrrolidin-1-yl)-2-cyclopropylamino-5-fluorobenzoic acid ethyl ester (Example 3e, 3.10 g, 10.4 mmol) in methanol (50 mL) and tetrahydrofuran (20 mL) is added 1N solution of sodium hydroxide (35 mL). The reaction mixture is stirred at 80° C. for 20 hours, cooled to room temperature, and diluted with ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1CC[NH]C1.C1CC1 | Other | CO.C(C)(=O)OCC.O1CCCC1 | 80 | 20 | CCOC(=O)c1cc(F)c(N2CCCC2)cc1NC1CC1>CO.C(C)(=O)OCC.O1CCCC1>O=C(O)c1cc(F)c(N2CCCC2)cc1NC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-389f49bf74d24494a85a7b0e9addedb2 | CCOC(=O)c1ccc(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1>>CC(C)(C)OC(=O)NC1CCN(c2ccc(C(=O)O)c(NC3CC3)c2F)C1 | C(C)OC(C1=C(C(=C(C=C1)N1CC(CC1)NC(=O)OC(C)(C)C)F)NC1CC1)=O.[OH-].[Na+]>>C(C)(C)(C)OC(=O)NC1CN(CC1)C1=C(C(=C(C(=O)O)C=C1)NC1CC1)F | CC[O:19][C:17]([c:16]1[cH:15][cH:14][c:13]([N:12]2[CH2:11][CH2:10][CH:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:27]2)[c:25]([F:26])[c:20]1[NH:21][CH:22]1[CH2:23][CH2:24]1)=[O:18]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH:14][cH:15][c:16]([C:17](... | CCOC(=O)c1ccc(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1 | CC(C)(C)OC(=O)NC1CCN(c2ccc(C(=O)O)c(NC3CC3)c2F)C1 | null | null | CO.O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cc(NC2CC2)cc(N2CCCC2)c1 | C-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] | 112.2 | [{"value": 112.2, "product": "C(C)(C)(C)OC(=O)NC1CN(CC1)C1=C(C(=C(C(=O)O)C=C1)NC1CC1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-[3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-2-cyclopropylamino-3-fluorobenzoic acid ethyl ester (Example 3j, 1.34 g, 3.29 mmol) and aqueous sodium hydroxide (2N, 20 mL) in tetrahydrofuran (20 mL) and methanol (20 mL) is refluxed for 1 hour. The solution is partially concentrated in vacuo, then acidifi... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]C1.c1ccccc1.C1CC1 | Other | CO.O1CCCC1 | null | null | CCOC(=O)c1ccc(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1>CO.O1CCCC1>CC(C)(C)OC(=O)NC1CCN(c2ccc(C(=O)O)c(NC3CC3)c2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a7f356a059ad4e31955c0bb42ee06496 | CCOC(=O)c1cc(Cl)c(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1>>CC(C)(C)OC(=O)NC1CCN(c2c(Cl)cc(C(=O)O)c(NC3CC3)c2F)C1 | C(C)OC(C1=C(C(=C(C(=C1)Cl)N1CC(CC1)NC(=O)OC(C)(C)C)F)NC1CC1)=O.[OH-].[Na+].CO>>C(C)(C)(C)OC(=O)NC1CN(CC1)C1=C(C(=C(C(=O)O)C=C1Cl)NC1CC1)F | CC[O:20][C:18]([c:17]1[cH:16][c:14]([Cl:15])[c:13]([N:12]2[CH2:11][CH2:10][CH:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:28]2)[c:26]([F:27])[c:21]1[NH:22][CH:23]1[CH2:24][CH2:25]1)=[O:19]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([c:13]2[c:14]([Cl:15])[cH:1... | CCOC(=O)c1cc(Cl)c(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1 | CC(C)(C)OC(=O)NC1CCN(c2c(Cl)cc(C(=O)O)c(NC3CC3)c2F)C1 | null | null | O1CCCC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cc(NC2CC2)cc(N2CCCC2)c1 | C-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] | 91.3 | [{"value": 91.3, "product": "C(C)(C)(C)OC(=O)NC1CN(CC1)C1=C(C(=C(C(=O)O)C=C1Cl)NC1CC1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-[3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-5-chloro-2-cyclopropylamino-3-fluorobenzoic acid ethyl ester (Example 3k, 2.00 g, 4.50 mmol) and aqueous sodium hydroxide (2.0N, 20 mL) in tetrahydrofuran (20 mL), and methanol (20 mL) is refluxed for 1 hour. The solution is partially concentrated in vacuo, ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]C1.c1ccccc1.C1CC1 | Other | O1CCCC1 | null | null | CCOC(=O)c1cc(Cl)c(N2CCC(NC(=O)OC(C)(C)C)C2)c(F)c1NC1CC1>O1CCCC1>CC(C)(C)OC(=O)NC1CCN(c2c(Cl)cc(C(=O)O)c(NC3CC3)c2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c17e0a2a9f6b4b76a94d85708a9a1372 | CCOC1(O[Si](C)(C)C)CC1.Nc1cc(F)c(F)cc1C(=O)O>>O=C(O)c1cc(F)c(F)cc1NC1CC1 | C(#N)[BH3-].[Na+].FC=1C=C(C(C(=O)O)=CC1F)N.C(C)(=O)O.C(C)OC1(CC1)O[Si](C)(C)C>>C1(CC1)NC1=C(C(=O)O)C=C(C(=C1)F)F | CCO[C:13]1(O[Si](C)(C)C)[CH2:14][CH2:15]1.[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[cH:10][c:11]1[NH2:12]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[cH:10][c:11]1[NH:12][CH:13]1[CH2:14][CH2:15]1 | CCOC1(O[Si](C)(C)C)CC1.Nc1cc(F)c(F)cc1C(=O)O | O=C(O)c1cc(F)c(F)cc1NC1CC1 | null | null | CO.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 98d8dfe2826a8c6338bf96b49d186b191d9599236f93ee5c29e87c823fb798b6 | ee949e00a6e6830a378056a2b6ec30dca5828fadb846505c80425caa906dfa25 | c1ccc(NC2CC2)cc1 | C-C-O-[C;H0;D4;+0:1]1(-O-[Si](-C)(-C)-C)-[C:2]-[C:3]-1.[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[O;D1;H0:9]=[C:8](-[O;D1;H1:10])-[c:7]:[c:5](-[NH;D2;+0:4]-[CH;D3;+0:1]1-[C:2]-[C:3]-1):[c:6] | 94.8 | [{"value": 94.8, "product": "C1(CC1)NC1=C(C(=O)O)C=C(C(=C1)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 4,5-difluoroanthranilic acid (1.13 g, 6.53 mmol) in anhydrous methanol (40 mL) is added molecular sieves (3 Å), acetic acid (3.70 mL, 65.3 mmol) and [(1-ethoxycyclopropyl)oxy]trimethylsilane (5.25 mL, 26.11 mmol). After 30 minutes, sodium cyanoborohydride (2.08 g, 32.64 mmol) is added, and the reaction... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine.Silyl protective group | Secondary amine | C1CC1 | C1CC1 | c1ccccc1.C1CC1 | HO- | CO.C(C)(=O)OCC | null | 0.5 | CCOC1(O[Si](C)(C)C)CC1.Nc1cc(F)c(F)cc1C(=O)O>CO.C(C)(=O)OCC>O=C(O)c1cc(F)c(F)cc1NC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0123970af20b4d508cbf2eed15a3b1af | Nc1ccc(F)cc1F.O=C(O)c1cc(F)c(F)cc1F>>O=C(O)c1cc(F)c(F)cc1Nc1ccc(F)cc1F | C(C)(C)[N-]C(C)C.[Li+].FC1=C(C(=O)O)C=C(C(=C1)F)F.C(CCC)[Li].FC1=C(N)C=CC(=C1)F.Cl.O1CCOCC1.C(C)(C)NC(C)C>>FC1=C(NC2=C(C(=O)O)C=C(C(=C2)F)F)C=CC(=C1)F | [NH2:12][c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][c:19]1[F:20].F[c:11]1[c:4]([C:2](=[O:1])[OH:3])[cH:5][c:6]([F:7])[c:8]([F:9])[cH:10]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[cH:10][c:11]1[NH:12][c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][c:19]1[F:20] | Nc1ccc(F)cc1F.O=C(O)c1cc(F)c(F)cc1F | O=C(O)c1cc(F)c(F)cc1Nc1ccc(F)cc1F | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:6]=[C:5](-[O;D1;H1:7])-[c:4](:[c:8]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:2]:[c:3] | 45 | [{"value": 45.0, "product": "FC1=C(NC2=C(C(=O)O)C=C(C(=C2)F)F)C=CC(=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 0.5 | HOUR | Lithium diisopropylamide is generated at −5° C. by combining diisopropylamine (7.2 mL, 51 mmol) and n-butyllithium (33 mL, 53 mmol) in anhydrous tetrahydrofuran (150 mL) under an inert atmosphere. After 0.5 hour, the solution is cooled to −78° C. and 2,4-difluoroaniline (3.46 mL, 34 mmol) is added and stirred for 2 hou... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | O1CCCC1 | -78 | 0.5 | Nc1ccc(F)cc1F.O=C(O)c1cc(F)c(F)cc1F>O1CCCC1>O=C(O)c1cc(F)c(F)cc1Nc1ccc(F)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ab04c13734c14f0eb76b4fd42879a70a | NC1CC1.O=C(O)c1cc(F)c(F)c(Cl)c1Br>>O=C(O)c1cc(F)c(F)c(Cl)c1NC1CC1 | BrC1=C(C(=O)O)C=C(C(=C1Cl)F)F.C1(CC1)N.C(C)(=O)[O-].[K+].C(C)N(CC)CC>>ClC=1C(=C(C(=O)O)C=C(C1F)F)NC1CC1 | [NH2:13][CH:14]1[CH2:15][CH2:16]1.Br[c:12]1[c:4]([C:2](=[O:1])[OH:3])[cH:5][c:6]([F:7])[c:8]([F:9])[c:10]1[Cl:11]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[c:10]([Cl:11])[c:12]1[NH:13][CH:14]1[CH2:15][CH2:16]1 | NC1CC1.O=C(O)c1cc(F)c(F)c(Cl)c1Br | O=C(O)c1cc(F)c(F)c(Cl)c1NC1CC1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NC2CC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2](-[Cl;D1;H0:3]):[c:4]):[c:5](-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]):[c:9].[NH2;D1;+0:10]-[C:11]1-[C:12]-[C:13]-1>>[Cl;D1;H0:3]-[c:2](:[c:4]):[c;H0;D3;+0:1](-[NH;D2;+0:10]-[C:11]1-[C:12]-[C:13]-1):[c:5](-[C:6](=[O;D1;H0:7])-[O;D1;H1:8]):[c:9] | 63.7 | [{"value": 63.7, "product": "ClC=1C(=C(C(=O)O)C=C(C1F)F)NC1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 16 | HOUR | In a sealed tube a mixture of 2-bromo-3-chloro-4,5-difluorobenzoic acid (Example 20, 7.96 g, 29.3 mmol), cyclopropyl amine (4.20 mL, 58.7 mmol), potassium acetate (5.77 g, 58.6 mmol), cupric acetate monohydrate (0.50 g, 2.5 mmol), and triethylamine (4.9 mL, 35.19 mmol) in isopropyl alcohol is stirred at 80° C. After 16... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC1 | HBr | C(C)(C)O | 80 | 16 | NC1CC1.O=C(O)c1cc(F)c(F)c(Cl)c1Br>C(C)(C)O>O=C(O)c1cc(F)c(F)c(Cl)c1NC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d6dea635e510434eb027e992714d250b | CC(C)(C)OC(=O)NN.O=C(O)c1cc(F)c(F)cc1NC1CC1>>CC(C)(C)OC(=O)NNC(=O)c1cc(F)c(F)cc1NC1CC1 | C1(CC1)NC1=C(C(=O)O)C=C(C(=C1)F)F.C(NN)(=O)OC(C)(C)C.C(C)N=C=NCCCN(C)C>>C(C)(C)(C)OC(=O)NNC(C1=C(C=C(C(=C1)F)F)NC1CC1)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][NH2:9].O[C:10](=[O:11])[c:12]1[cH:13][c:14]([F:15])[c:16]([F:17])[cH:18][c:19]1[NH:20][CH:21]1[CH2:22][CH2:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][NH:9][C:10](=[O:11])[c:12]1[cH:13][c:14]([F:15])[c:16]([F:17])[cH:18][c:19]1[NH:20][CH:21]1[CH2:2... | CC(C)(C)OC(=O)NN.O=C(O)c1cc(F)c(F)cc1NC1CC1 | CC(C)(C)OC(=O)NNC(=O)c1cc(F)c(F)cc1NC1CC1 | null | null | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 1bfc5046b360bb38c235d234cdd252f03d34a0792ef57a2cdb032482310d9689 | 1f93e2b4a6ed796a4645f0486672499ca332a9bc5c180e504c9a46d8eb8d844d | c1ccc(NC2CC2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[#7:13]-[NH2;D1;+0:14]>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[#7:13]-[NH;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 81.4 | [{"value": 81.4, "product": "C(C)(C)(C)OC(=O)NNC(C1=C(C=C(C(=C1)F)F)NC1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 2-cyclopropylamino-4,5-difluorobenzoic acid (Example 5) (1.32 g, 6.19 mmol) and tert-butyl carbazate (1.30 g, 9.75 mmol) in dichloromethane (30 mL) is added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (1.87 g, 9.75 mmol). After 16 hours, the reaction mixture is diluted with dichloromethane and washe... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carboxylic acid | Acylhydrazine.Acylhydrazine | null | null | c1ccccc1.C1CC1 | HO- | ClCCl | null | 16 | CC(C)(C)OC(=O)NN.O=C(O)c1cc(F)c(F)cc1NC1CC1>ClCCl>CC(C)(C)OC(=O)NNC(=O)c1cc(F)c(F)cc1NC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eeeb0d9ca8654a97b94c5952a45d29e4 | CC(C)(C)OC(=O)NN.O=C(O)c1cc(F)c(F)cc1Nc1ccc(F)cc1F>>CC(C)(C)OC(=O)N(N)C(=O)c1cc(F)c(F)cc1Nc1ccc(F)cc1F | FC1=C(NC2=C(C(=O)O)C=C(C(=C2)F)F)C=CC(=C1)F.C(NN)(=O)OC(C)(C)C.C(C)N=C=NCCCN(C)C>>C(C)(C)(C)OC(=O)N(N)C(C1=C(C=C(C(=C1)F)F)NC1=C(C=C(C=C1)F)F)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][NH2:9].O[C:10](=[O:11])[c:12]1[cH:13][c:14]([F:15])[c:16]([F:17])[cH:18][c:19]1[NH:20][c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][c:27]1[F:28]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([NH2:9])[C:10](=[O:11])[c:12]1[cH:13][c:14]([F:15])[c:16]([F:17])[cH... | CC(C)(C)OC(=O)NN.O=C(O)c1cc(F)c(F)cc1Nc1ccc(F)cc1F | CC(C)(C)OC(=O)N(N)C(=O)c1cc(F)c(F)cc1Nc1ccc(F)cc1F | null | null | ClCCl | Protection | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | c98ee5b7ab674ace8788dc72836dff1f14049f74d05f98c07e40c7e2dbb84b79 | ad033db82ebb2e7a535de94b1f0f3d4f69c3d8512618c4288ab7622a9f6af1cc | c1ccc(Nc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[NH;D2;+0:13]-[N;D1;H2:14]>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[N;H0;D3;+0:13](-[N;D1;H2:14])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 72.5 | [{"value": 72.5, "product": "C(C)(C)(C)OC(=O)N(N)C(C1=C(C=C(C(=C1)F)F)NC1=C(C=C(C=C1)F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 2-(2,4-difluoroanilino)-4,5-difluorobenzoic acid (Example 5, 2.18 g, 7.6 mmol) and tert-butyl carbazate (1.57 g, 11.8 mmol) in dichloromethane (30 mL) is added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (2.25 g, 11.77 mmol). After stirring for 16 hours at room temperature, the reaction mixture is d... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carbamic ester.Carboxylic acid | Acylhydrazine.Acylhydrazine | null | null | c1ccccc1.c1ccccc1 | HO- | ClCCl | null | 16 | CC(C)(C)OC(=O)NN.O=C(O)c1cc(F)c(F)cc1Nc1ccc(F)cc1F>ClCCl>CC(C)(C)OC(=O)N(N)C(=O)c1cc(F)c(F)cc1Nc1ccc(F)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2215a032e5f9454f83cc5b8245d8b56f | CC(C)(C)OC(=O)NN.O=C(O)c1cc(F)c(F)c(Cl)c1NC1CC1>>CC(C)(C)OC(=O)N(N)C(=O)c1cc(F)c(F)c(Cl)c1NC1CC1 | ClC=1C(=C(C(=O)O)C=C(C1F)F)NC1CC1.C(NN)(=O)OC(C)(C)C.C(C)N=C=NCCCN(C)C>>C(C)(C)(C)OC(=O)N(N)C(C1=C(C(=C(C(=C1)F)F)Cl)NC1CC1)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][NH2:9].O[C:10](=[O:11])[c:12]1[cH:13][c:14]([F:15])[c:16]([F:17])[c:18]([Cl:19])[c:20]1[NH:21][CH:22]1[CH2:23][CH2:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([NH2:9])[C:10](=[O:11])[c:12]1[cH:13][c:14]([F:15])[c:16]([F:17])[c:18]([Cl:19])[c:20]1[NH... | CC(C)(C)OC(=O)NN.O=C(O)c1cc(F)c(F)c(Cl)c1NC1CC1 | CC(C)(C)OC(=O)N(N)C(=O)c1cc(F)c(F)c(Cl)c1NC1CC1 | null | null | ClCCl | Protection | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | c98ee5b7ab674ace8788dc72836dff1f14049f74d05f98c07e40c7e2dbb84b79 | ad033db82ebb2e7a535de94b1f0f3d4f69c3d8512618c4288ab7622a9f6af1cc | c1ccc(NC2CC2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[NH;D2;+0:13]-[N;D1;H2:14]>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[#8:10]-[C:11](=[O;D1;H0:12])-[N;H0;D3;+0:13](-[N;D1;H2:14])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 63.1 | [{"value": 63.1, "product": "C(C)(C)(C)OC(=O)N(N)C(C1=C(C(=C(C(=C1)F)F)Cl)NC1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of 3-chloro-2-cyclopropylamino-4,5-difluorobenzoic acid (Example 5d, 2.09 g, 8.45 mmol) in dichloromethane (30 mL) is added tert-butyl carbazate (1.67 g, 12.7 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (2.43 g, 12.7 mmol). After 16 hours, the reaction mixture is diluted with dichloromethane ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Carbamic ester.Carboxylic acid | Acylhydrazine.Acylhydrazine | null | null | c1ccccc1.C1CC1 | HO- | ClCCl | null | 16 | CC(C)(C)OC(=O)NN.O=C(O)c1cc(F)c(F)c(Cl)c1NC1CC1>ClCCl>CC(C)(C)OC(=O)N(N)C(=O)c1cc(F)c(F)c(Cl)c1NC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-723272e4c50d4750ba96359bf38303f9 | COc1c(N2CC(C(C)N)C(C)(C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12.COc1c(N2CC(C(C)N)C(C)(C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12.COc1c(N2CC(C(C)NC(=O)OC(C)(C)C)C(C)(C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12.Cl>>N[C@@H]1CN(c2c(F)cc3c(=O)n(N)c(=O)n(C4CC4)c3c2Cl)C[C@H]1c1ccc(O)cc1 | Cl.NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1CC(C(C1)C(C)N)(C)C)OC)C1CC1)=O.Cl.NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1CC(C(C1)C(C)N)(C)C)OC)C1CC1)=O.C(C)(C)(C)OC(NC(C)C1CN(CC1(C)C)C1=C(C=C2C(N(C(N(C2=C1OC)C1CC1)=O)N)=O)F)=O>>Cl.NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1C[C@H]([C@@H](C1)C1=CC=C(C=C1)O)N)Cl)C1CC1)=O | COc1c(N2CC(C(C)N)C(C)(C)C2)c(F)cc2c(=O)n(N)c(=O)n([CH:26]3[CH2:27][CH2:28]3)c12.CO[c:32]1c(N2CC(C(C)N)C(C)(C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3C[CH2:31]3)c21.CO[c:22]1[c:6]([N:5]2[CH2:4][CH:3]([CH:25](C)[NH:2][C:29](OC(C)(C)C)=[O:30])C(C)(C)[CH2:24]2)[c:7]([F:8])[cH:9][c:10]2[c:11](=[O:12])[n:13]([NH2:14])[c:15](=[O:16])[n:1... | COc1c(N2CC(C(C)N)C(C)(C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12.COc1c(N2CC(C(C)N)C(C)(C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12.COc1c(N2CC(C(C)NC(=O)OC(C)(C)C)C(C)(C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12.Cl | N[C@@H]1CN(c2c(F)cc3c(=O)n(N)c(=O)n(C4CC4)c3c2Cl)C[C@H]1c1ccc(O)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1198f7ad564668c686597f068eb2d77a7f802ab881b1a1b5782f67d90e62603c | 4aafd3fbdb3033daa035ea8e47db79c24910ad3ef71801528a6032fcf9791bf4 | O=c1[nH]c(=O)n(C2CC2)c2cc(N3CC[C@H](c4ccccc4)C3)ccc12 | C-O-[c;H0;D3;+0:1](:[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1-[C:8]):[c:9](-[#7:10]1-[C:11]-[CH;D3;+0:12](-[CH;D3;+0:13](-C)-[NH;D2;+0:14]-[C;H0;D3;+0:15](=[O;H0;D1;+0:16])-O-C(-C)(-C)-C)-C(-C)(-C)-[CH2;D2;+0:17]-1):[c:18].C-O-[c;H0;D3;+0:19]1:c(-N2-C-C(-C(-C)-N)-C(-C)(-C)-C-2):c(-F):c:c2:c(=O):n(-N):c(=O):n(-C3-C-[... | null | [] | null | null | null | null | (gggg) 3-Amino-7-[4-(1-aminoethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-1H-quinazoline-2,4-dione hydrochloride (Compound 86) (mp 230° C., MS ES: m/z 406 (MH+)) from {1-[1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-7-yl)-4,4-dimethylpyrrolidin-3-yl]ethyl}car... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carbamic ester.Ether.Ether.Ether.Ether.Primary amine.Primary amine.Primary amine.Primary amine.Tertiary amine.Tertiary amine.Boc | Aromatic halide.Aromatic alcohol.Primary amine | C1CCNC1.c1ccc2ncncc2c1.C1CC1.C1CCNC1.c1ccc2ncncc2c1.C1CC1.C1CC[NH]C1.c1ccc2ncncc2c1 | C1CC[NH]C1.c1ccc2ncncc2c1.c1ccccc1 | C1CC[NH]C1.c1ccc2ncncc2c1.C1CC1.c1ccccc1 | HF | null | null | null | COc1c(N2CC(C(C)N)C(C)(C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12.COc1c(N2CC(C(C)N)C(C)(C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12.COc1c(N2CC(C(C)NC(=O)OC(C)(C)C)C(C)(C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12.Cl>>N[C@@H]1CN(c2c(F)cc3c(=O)n(N)c(=O)n(C4CC4)c3c2Cl)C[C@H]1c1ccc(O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-78d431e5d1344941ac084e1b69f85abf | Cc1c(N2CC3C(C2)C3NC(=O)OC(C)(C)C)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12.Cc1c(N2CC3C(N)C3C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12>>Cc1c(N2CC(C(C)N)C(C)(C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12 | Cl.NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1CC2C(C2C1)N)C)C1CC1)=O.Cl.NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1CC2C(C2C1)N)C)C1CC1)=O.C(C)(C)(C)OC(NC1C2CN(CC12)C1=C(C=C2C(N(C(N(C2=C1C)C1CC1)=O)N)=O)F)=O>>Cl.NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1CC(C(C1)C(C)N)(C)C)C)C1CC1)=O | CC(C)(C)OC(=O)[NH:9][CH:7]1[CH:6]2[CH2:5][N:4]([c:3]3[c:2]([CH3:1])[c:28]4[c:17]([cH:16][c:14]3[F:15])[c:18](=[O:19])[n:20]([NH2:21])[c:22](=[O:23])[n:24]4[CH:25]3[CH2:26][CH2:27]3)[CH2:11][CH:10]21.Cc1c(N2CC3[CH:8](N)[CH:12]3[CH2:13]2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12>>[CH3:1][c:2]1[c:3]([N:4]2[CH2:5][CH:6]([CH:7]([CH3... | Cc1c(N2CC3C(C2)C3NC(=O)OC(C)(C)C)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12.Cc1c(N2CC3C(N)C3C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12 | Cc1c(N2CC(C(C)N)C(C)(C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0e6ab62436720bc15a1cb658e7094c26f03aa45e11575f623e55e0444c758050 | 8fe70cbebf6ccf1f29514aa2b36dba78ff5ca891742687bf689e78cf1f7960ba | O=c1[nH]c(=O)n(C2CC2)c2cc(N3CCCC3)ccc12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[CH;D3;+0:2]1-[C:3]2-[C:4]-[N;H0;D3;+0:5](-[c:6](:[c:7]):[c:8]:[c:9]:[#7;a:10])-[CH2;D2;+0:11]-[CH;D3;+0:12]-2-1.C-c1:c(-N2-C-C3-[CH;D3;+0:13](-[CH2;D2;+0:14]-2)-[CH;D3;+0:15]-3-N):c(-F):c:c2:c(=O):n(-N):c(=O):n(-C3-C-C-3):c:1:2>>[#7;a:10]:[c:9]:[c:8]:[c:6](-[N;H0;D3;+0:5]1-[C:4]-[C:3](... | null | [] | null | null | null | null | (aaaaaa) 3-Amino-7-(6-amino-3-azabicyclo[3.1.0]hex-3-yl)-1-cyclopropyl-6-fluoro-8-methyl-1H-quinazoline-2,4-dione hydrochloride (Compound 134) (mp 180–182° C., MS ES: m/z 346 (MH+)) from [3-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxo-1,2,3,4-tetrahydroquinazolin-7-yl)-3-azabicyclo[3.1.0]hex-6-yl]carbamic acid te... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Primary amine.Primary amine.Tertiary amine.Tertiary amine.Boc | Primary amine.Tertiary amine | C1[NH]CC2CC12.C1NCC2CC12.c1ccc2ncncc2c1.C1CC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccc2ncncc2c1.C1CC1 | HF | null | null | null | Cc1c(N2CC3C(C2)C3NC(=O)OC(C)(C)C)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12.Cc1c(N2CC3C(N)C3C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12>>Cc1c(N2CC(C(C)N)C(C)(C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1844604fef6b40a99dc875eff2d94f9d | CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(F)c3c(=O)n(NC(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2F)C1.NCc1ccccc1>>CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(NCc3ccccc3)c3c(=O)n(NC(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2F)C1 | C(C)(C)(C)OC(NN1C(N(C2=C(C(=C(C(=C2C1=O)F)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)C1CC1)=O)=O.C(C)N(CC)CC.C(C1=CC=CC=C1)N>>C(C)(C)(C)OC(NN1C(N(C2=C(C(=C(C(=C2C1=O)NCC1=CC=CC=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)C1CC1)=O)=O | F[c:16]1[c:14]([F:15])[c:13]([N:12]2[CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:46]2)[c:44]([F:45])[c:43]2[c:25]1[c:26](=[O:27])[n:28]([NH:29][C:30](=[O:31])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[c:37](=[O:38])[n:39]2[CH:40]1[CH2:41][CH2:42]1.[NH2:17][CH2:18][c:19]1[cH:20][cH:... | CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(F)c3c(=O)n(NC(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2F)C1.NCc1ccccc1 | CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(NCc3ccccc3)c3c(=O)n(NC(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2F)C1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1[nH]c(=O)n(C2CC2)c2cc(N3CCCC3)cc(NCc3ccccc3)c12 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4]:[c:5]:[c:6]2:[#7;a:7](-[C:8]):[c:9]:[#7;a:10](-[#7:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[C;D1;H3:18]):[c:19](=[O;D1;H0:20]):[c:21]:2:1.[NH2;D1;+0:22]-[C:23]-[c:24]>>[C:8]-[#7;a:7]1:[c:9]:[#7;a:10](-[#7:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]... | 86.8 | [{"value": 86.8, "product": "C(C)(C)(C)OC(NN1C(N(C2=C(C(=C(C(=C2C1=O)NCC1=CC=CC=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)C1CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of {7-[(S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-1-cyclopropyl-1,4-dihydro-2,4-dioxo-5,6,8-trifluoro-2H-quinazolin-3-yl}carbamic acid tert-butyl ester from Example 8 (0.51 g, 0.914 mmol), triethylamine (1.3 mL, 9.3 mmol), and benzylamine (0.50 mL, 4.6 mmol) in dimethyl sulfoxide (7.5 mL) is heated at ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | C1CC[NH]C1.c1ccccc1.c1ccc2ncncc2c1.C1CC1 | HF | CS(=O)C | null | null | CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(F)c3c(=O)n(NC(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2F)C1.NCc1ccccc1>CS(=O)C>CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(NCc3ccccc3)c3c(=O)n(NC(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-47358ccb45f14dbb802e1a7480724754 | CI.CN(C(=O)OC(C)(C)C)[C@H]1CCN(c2c(F)cc3c(=O)n(NC(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2Cl)C1>>CN(C(=O)OC(C)(C)C)[C@H]1CCN(c2c(F)cc3c(=O)n(N(C)C(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2Cl)C1 | IC.C(C)(C)(C)OC(NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1C[C@H](CC1)N(C)C(=O)OC(C)(C)C)Cl)C1CC1)=O)=O.[H-].[Na+]>>C(C)(C)(C)OC(N(C)N1C(N(C2=C(C(=C(C=C2C1=O)F)N1C[C@H](CC1)N(C)C(=O)OC(C)(C)C)Cl)C1CC1)=O)=O | I[CH3:23].[CH3:1][N:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[C@H:10]1[CH2:11][CH2:12][N:13]([c:14]2[c:15]([F:16])[cH:17][c:18]3[c:19](=[O:20])[n:21]([NH:22][C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[c:31](=[O:32])[n:33]([CH:34]4[CH2:35][CH2:36]4)[c:37]3[c:38]2[Cl:39])[CH2:40]1>>[CH3:1][N:2]([C... | CI.CN(C(=O)OC(C)(C)C)[C@H]1CCN(c2c(F)cc3c(=O)n(NC(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2Cl)C1 | CN(C(=O)OC(C)(C)C)[C@H]1CCN(c2c(F)cc3c(=O)n(N(C)C(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2Cl)C1 | null | null | CN(C=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 29c841ae076cb6ee785aad2a4e3ce1a9b47357d7ad25657b8d9991b1347f5721 | c485eddcb40c5a0d396ffdb624041effa09ee4f5ca2ecce3fe13077cf65004ed | O=c1[nH]c(=O)n(C2CC2)c2cc(N3CCCC3)ccc12 | I-[CH3;D1;+0:1].[#7;a:2]:[c:3]:[#7;a:4](-[NH;D2;+0:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12]):[c:13]>>[#7;a:2]:[c:3]:[#7;a:4](-[N;H0;D3;+0:5](-[CH3;D1;+0:1])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12]):[c:13] | 48.2 | [{"value": 48.2, "product": "C(C)(C)(C)OC(N(C)N1C(N(C2=C(C(=C(C=C2C1=O)F)N1C[C@H](CC1)N(C)C(=O)OC(C)(C)C)Cl)C1CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of {7-[(S)-3-(tert-butoxycarbonyl-N-methylamino)-pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl}carbamic acid tert-butyl ester from Example 8 (0.238 g, 0.421 mmol) in N,N-dimethylformamide (5 mL) at −78° C. under nitrogen atmosphere is added sodium hydride (60% d... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester | Carbamic ester | null | null | C1CC[NH]C1.c1ccc2ncncc2c1.C1CC1 | HI | CN(C=O)C.C(C)(=O)OCC | null | 0.5 | CI.CN(C(=O)OC(C)(C)C)[C@H]1CCN(c2c(F)cc3c(=O)n(NC(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2Cl)C1>CN(C=O)C.C(C)(=O)OCC>CN(C(=O)OC(C)(C)C)[C@H]1CCN(c2c(F)cc3c(=O)n(N(C)C(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2Cl)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c978877a17c84bafbb196b62c0e17983 | CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(NCc3ccccc3)c3c(=O)n(NC(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2F)C1>>CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(N)c3c(=O)n(NC(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2F)C1 | C(C)(C)(C)OC(NN1C(N(C2=C(C(=C(C(=C2C1=O)NCC1=CC=CC=C1)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)C1CC1)=O)=O>>C(C)(C)(C)OC(NN1C(N(C2=C(C(=C(C(=C2C1=O)N)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)C1CC1)=O)=O | c1ccc(C[NH:17][c:16]2[c:14]([F:15])[c:13]([N:12]3[CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:39]3)[c:37]([F:38])[c:36]3[c:18]2[c:19](=[O:20])[n:21]([NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[c:30](=[O:31])[n:32]3[CH:33]2[CH2:34][CH2:35]2)cc1>>[CH3:1][C:2]([CH... | CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(NCc3ccccc3)c3c(=O)n(NC(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2F)C1 | CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(N)c3c(=O)n(NC(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2F)C1 | null | [OH-].[OH-].[Pd+2] | O1CCCC1 | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | O=c1[nH]c(=O)n(C2CC2)c2cc(N3CCCC3)ccc12 | [#7;a:1]:[c:2]:[c:3](:[c:4]:[#7;a:5]):[c:6](-[NH;D2;+0:7]-C-c1:c:c:c:c:c:1):[c:8]>>[#7;a:1]:[c:2]:[c:3](:[c:4]:[#7;a:5]):[c:6](-[NH2;D1;+0:7]):[c:8] | 76 | [{"value": 76.0, "product": "C(C)(C)(C)OC(NN1C(N(C2=C(C(=C(C(=C2C1=O)N)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)C1CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | {7-[(S)-3-(tert-Butoxycarbonylamino)pyrrolidin-1-yl]-5-benzylamino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-2,4-dioxo-2H-quinazolin-3-yl}carbamic acid tert-butyl ester from Example 10 (0.435 g, 0.676 mmol) in tetrahydrofuran (20 mL) is hydrogenated at room temperature and atmospheric pressure over 20% palladium hydroxide... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | C1CC[NH]C1.c1ccc2ncncc2c1.C1CC1 | Other | [OH-].[OH-].[Pd+2].O1CCCC1 | null | null | CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(NCc3ccccc3)c3c(=O)n(NC(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2F)C1>[OH-].[OH-].[Pd+2].O1CCCC1>CC(C)(C)OC(=O)N[C@H]1CCN(c2c(F)c(N)c3c(=O)n(NC(=O)OC(C)(C)C)c(=O)n(C4CC4)c3c2F)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c2d5044022f14e53baf14d00dca00803 | CC(C)(C)OC(=O)N(N)C(=O)c1cc(F)c(F)c(Cl)c1NC1CC1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>CC(C)(C)OC(=O)Nn1c(=O)c2cc(F)c(F)c(Cl)c2n(C2CC2)c1=O | C(C)(C)(C)OC(=O)N(N)C(C1=C(C(=C(C(=C1)F)F)Cl)NC1CC1)=O.C([O-])([O-])=O.[K+].[K+].ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl.O1CCCC1>>C(C)(C)(C)OC(NN1C(N(C2=C(C(=C(C=C2C1=O)F)F)Cl)C1CC1)=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:9]([NH2:8])[C:10](=[O:11])[c:12]1[cH:13][c:14]([F:15])[c:16]([F:17])[c:18]([Cl:19])[c:20]1[NH:21][CH:22]1[CH2:23][CH2:24]1.ClC(Cl)(Cl)O[C:25](OC(Cl)(Cl)Cl)=[O:26]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][n:9]1[c:10](=[O:11])[c:12]2[cH:13][c:14]([F:15])[c... | CC(C)(C)OC(=O)N(N)C(=O)c1cc(F)c(F)c(Cl)c1NC1CC1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | CC(C)(C)OC(=O)Nn1c(=O)c2cc(F)c(F)c(Cl)c2n(C2CC2)c1=O | null | null | C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | c6b4d02c6c0bff2689f07d1c645d1cae1ec2640b111b023685404790b9cae33b | 4cbf753e6b20db27fb12d18a32e4abed7429535b4341cc531aae4e1f32e2aca8 | O=c1[nH]c(=O)n(C2CC2)c2ccccc12 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[C;D1;H3:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[#8:7]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[N;H0;D3;+0:10](-[NH2;D1;+0:11])-[C;H0;D3;+0:12](=[O;D1;H0:13])-[c:14](:[c:15]):[c:16](-[NH;D2;+0:17]-[C:18]1-[C:19]-[C:20]-1):[c:21]>>[C;D1;H3:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H... | null | [] | null | null | null | null | To a solution of (3-chloro-2-cyclopropylamino-4,5-difluorobenzoyl)-hydrazinecarboxylic acid tert-butyl ester (Example 6c) (1.93 g, 5.34 mmol) in tetrahydrofuran (50 mL) is added potassium carbonate (3.69 g, 26.7 mol) and triphosgene (2.06 g, 6.95 mmol). The reaction mixture is refluxed for 90 minutes, cooled to room te... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine.Trichloro group.Trichloro group.Carbamic ester.Carbonic Ester.Ether.Secondary amine.Boc | Carbamic ester.Ether.Boc | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CC1 | HCl | C(C)(=O)OCC | null | null | CC(C)(C)OC(=O)N(N)C(=O)c1cc(F)c(F)c(Cl)c1NC1CC1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>C(C)(=O)OCC>CC(C)(C)OC(=O)Nn1c(=O)c2cc(F)c(F)c(Cl)c2n(C2CC2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7f92a3d7fb874808929e1d951998575f | NN(Cc1ccccc1)Cc1ccccc1.Nc1cc(F)c(F)cc1C(=O)O>>Nc1cc(F)c(F)cc1C(=O)NN(Cc1ccccc1)Cc1ccccc1 | FC=1C=C(C(C(=O)O)=CC1F)N.C(C1=CC=CC=C1)N(N)CC1=CC=CC=C1.Cl.C(C)N=C=NCCCN(C)C>>C(C1=CC=CC=C1)N(NC(C1=C(C=C(C(=C1)F)F)N)=O)CC1=CC=CC=C1 | [NH2:12][N:13]([CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.O[C:10]([c:9]1[c:2]([NH2:1])[cH:3][c:4]([F:5])[c:6]([F:7])[cH:8]1)=[O:11]>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[c:6]([F:7])[cH:8][c:9]1[C:10](=[O:11])[NH:12][N:13]([CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19... | NN(Cc1ccccc1)Cc1ccccc1.Nc1cc(F)c(F)cc1C(=O)O | Nc1cc(F)c(F)cc1C(=O)NN(Cc1ccccc1)Cc1ccccc1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 87776deec7c8d787307af11af64c4c1226af5b5e46e4fe8124762f384e2eebf3 | 82203b4f77b2f7d17908f28dcc1ecc7f616d152f963b273ffea1254f61a0fe2d | O=C(NN(Cc1ccccc1)Cc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#7:7](-[C:8])-[NH2;D1;+0:9]>>[C:6]-[#7:7](-[C:8])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 157.5 | [{"value": 157.5, "product": "C(C1=CC=CC=C1)N(NC(C1=C(C=C(C(=C1)F)F)N)=O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 18 | HOUR | 4,5-Difluoroanthranilic acid (4.73 g, 27.3 mmol) and N,N-dibenzylhydrazine (8.69 g, 42 mmol) are combined in 200 mL of methylene chloride. 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDAC) (7.85 g, 41 mmol) is then added to this solution, and the mixture is stirred for 18 hours at 25° C., The solution ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carboxylic acid | Acylhydrazine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | 25 | 18 | NN(Cc1ccccc1)Cc1ccccc1.Nc1cc(F)c(F)cc1C(=O)O>C(Cl)Cl>Nc1cc(F)c(F)cc1C(=O)NN(Cc1ccccc1)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-80072c018d95452cb4a32b07e670454c | Nc1cc(F)c(F)cc1C(=O)NN(Cc1ccccc1)Cc1ccccc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>O=c1[nH]c2cc(F)c(F)cc2c(=O)n1N(Cc1ccccc1)Cc1ccccc1 | C(C1=CC=CC=C1)N(NC(C1=C(C=C(C(=C1)F)F)N)=O)CC1=CC=CC=C1.ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl.C(=O)(O)[O-].[Na+]>>C(C1=CC=CC=C1)N(N1C(NC2=CC(=C(C=C2C1=O)F)F)=O)CC1=CC=CC=C1 | [NH2:3][c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[cH:10][c:11]1[C:12](=[O:13])[NH:14][N:15]([CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1.ClC(Cl)(Cl)O[C:2](OC(Cl)(Cl)Cl)=[O:1]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([F:7])[c:8]([F:9])[cH:10][c:11]2[c:12](=[O:13])[n:14]1[... | Nc1cc(F)c(F)cc1C(=O)NN(Cc1ccccc1)Cc1ccccc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | O=c1[nH]c2cc(F)c(F)cc2c(=O)n1N(Cc1ccccc1)Cc1ccccc1 | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 3088685657879b5d46a8d3bdf91412bc59e92855b7b82124def1c1f5ec65dff3 | cbc1e68b05ec8e5493d5786cee084ad7a55547a0f4620c6ee39c1ab17c8df5ac | O=c1[nH]c2ccccc2c(=O)n1N(Cc1ccccc1)Cc1ccccc1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[C:3]-[#7:4](-[C:5])-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:9](:[c:10]):[c:11](-[NH2;D1;+0:12]):[c:13]>>[C:3]-[#7:4](-[C:5])-[n;H0;D3;+0:6]1:[c;H0;D3;+0:7](=[O;D1;H0:8]):[c:9](:[c:10]):[c:11](:[c:13]):[nH;D2;+0:12]:[c;H0;D3;+0:1]:1=[O;D1;H0:2] | 198.7 | [{"value": 198.7, "product": "C(C1=CC=CC=C1)N(N1C(NC2=CC(=C(C=C2C1=O)F)F)=O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 20 | HOUR | 2-Amino-4,5-difluorobenzoic acid, 2,2-dibenzylhydrazide (Example 15) (0.81 g, 2.2 mmol) and triphosgene (0.33 g, 1.1 mmol) are combined in 100 mL of methylene chloride and stirred at 25° C. for 20 hours. The solution is poured into 200 mL of saturated NaHCO3, the layers are separated, and the aqueous layer is washed th... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Trichloro group.Trichloro group.Carbonic Ester.Primary amine | null | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | 25 | 20 | Nc1cc(F)c(F)cc1C(=O)NN(Cc1ccccc1)Cc1ccccc1.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>C(Cl)Cl>O=c1[nH]c2cc(F)c(F)cc2c(=O)n1N(Cc1ccccc1)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-daaaaa8f0d4e49baa153f8600eb11663 | BrCC1CC1.O=c1[nH]c2cc(F)c(F)cc2c(=O)n1N(Cc1ccccc1)Cc1ccccc1>>O=c1c2cc(F)c(F)cc2n(CC2CC2)c(=O)n1N(Cc1ccccc1)Cc1ccccc1 | C(C1=CC=CC=C1)N(N1C(NC2=CC(=C(C=C2C1=O)F)F)=O)CC1=CC=CC=C1.[H-].[Na+].BrCC1CC1>>C(C1=CC=CC=C1)N(N1C(N(C2=CC(=C(C=C2C1=O)F)F)CC1CC1)=O)CC1=CC=CC=C1 | Br[CH2:12][CH:13]1[CH2:14][CH2:15]1.[O:1]=[c:2]1[c:3]2[cH:4][c:5]([F:6])[c:7]([F:8])[cH:9][c:10]2[nH:11][c:16](=[O:17])[n:18]1[N:19]([CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[CH2:27][c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[O:1]=[c:2]1[c:3]2[cH:4][c:5]([F:6])[c:7]([F:8])[cH:9][c:10]2[n:11]([CH2:12][CH:13... | BrCC1CC1.O=c1[nH]c2cc(F)c(F)cc2c(=O)n1N(Cc1ccccc1)Cc1ccccc1 | O=c1c2cc(F)c(F)cc2n(CC2CC2)c(=O)n1N(Cc1ccccc1)Cc1ccccc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0b0179903a04a1706fdb5bd83526eacf6acd2b47a87012dec86fcbe52dd05a28 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1c2ccccc2n(CC2CC2)c(=O)n1N(Cc1ccccc1)Cc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[#7:5]-[#7;a:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[nH;D2;+0:11]:[c:12]:1=[O;D1;H0:13]>>[#7:5]-[#7;a:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[C:2]2-[C:3]-[C:4]-2):[c:12]:1=[O;D1;H0:13] | 67 | [{"value": 67.0, "product": "C(C1=CC=CC=C1)N(N1C(N(C2=CC(=C(C=C2C1=O)F)F)CC1CC1)=O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 3-dibenzylamino-6,7-difluoro-1H-quinazoline-2,4-dione (Example 16) (0.43 g, 1.1 mmol) in 10 mL of N,N-dimethylformamide is added to a suspension of sodium hydride (0.05 g, 1.3 mmol) in 10 mL of N,N-dimethylformamide and stirred for 30 minutes. Bromomethylcyclopropane (0.16 mL, 1.6 mmol) is added, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CC1.c1ccccc1.c1ccccc1 | HBr | CN(C=O)C | null | 0.5 | BrCC1CC1.O=c1[nH]c2cc(F)c(F)cc2c(=O)n1N(Cc1ccccc1)Cc1ccccc1>CN(C=O)C>O=c1c2cc(F)c(F)cc2n(CC2CC2)c(=O)n1N(Cc1ccccc1)Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-de33f49a4f9a4548b0cd9c65b986092f | CCI.O=c1[nH]c2cc(F)c(F)cc2c(=O)n1N(Cc1ccccc1)Cc1ccccc1>>CCn1c(=O)n(N(Cc2ccccc2)Cc2ccccc2)c(=O)c2cc(F)c(F)cc21 | C(C1=CC=CC=C1)N(N1C(NC2=CC(=C(C=C2C1=O)F)F)=O)CC1=CC=CC=C1.[H-].[Na+].C(C)I>>C(C1=CC=CC=C1)N(N1C(N(C2=CC(=C(C=C2C1=O)F)F)CC)=O)CC1=CC=CC=C1 | I[CH2:2][CH3:1].[nH:3]1[c:4](=[O:5])[n:6]([N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:22](=[O:23])[c:24]2[cH:25][c:26]([F:27])[c:28]([F:29])[cH:30][c:31]12>>[CH3:1][CH2:2][n:3]1[c:4](=[O:5])[n:6]([N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[... | CCI.O=c1[nH]c2cc(F)c(F)cc2c(=O)n1N(Cc1ccccc1)Cc1ccccc1 | CCn1c(=O)n(N(Cc2ccccc2)Cc2ccccc2)c(=O)c2cc(F)c(F)cc21 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0b0179903a04a1706fdb5bd83526eacf6acd2b47a87012dec86fcbe52dd05a28 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1[nH]c2ccccc2c(=O)n1N(Cc1ccccc1)Cc1ccccc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[#7:3]-[#7;a:4]1:[c:5]:[c:6]:[c:7](:[c:8]):[nH;D2;+0:9]:[c:10]:1=[O;D1;H0:11]>>[#7:3]-[#7;a:4]1:[c:5]:[c:6]:[c:7](:[c:8]):[n;H0;D3;+0:9](-[CH2;D2;+0:1]-[C;D1;H3:2]):[c:10]:1=[O;D1;H0:11] | 73.3 | [{"value": 73.3, "product": "C(C1=CC=CC=C1)N(N1C(N(C2=CC(=C(C=C2C1=O)F)F)CC)=O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 3-dibenzylamino-6,7-difluoro-1H-quinazoline-2,4-dione (Example 16) (0.43 g, 1.1 mmol) in 10 mL of N,N-dimethylformamide is added to a suspension of sodium hydride (0.05 g, 1.3 mmol) in 10 mL of N,N-dimethylformamide and stirred for 30 minutes. Ethyl iodide (0.13 mL, 1.6 mmol) is added, and the mixture is ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccccc1.c1ccc2ncncc2c1 | HI | CN(C=O)C | null | 0.5 | CCI.O=c1[nH]c2cc(F)c(F)cc2c(=O)n1N(Cc1ccccc1)Cc1ccccc1>CN(C=O)C>CCn1c(=O)n(N(Cc2ccccc2)Cc2ccccc2)c(=O)c2cc(F)c(F)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-39a15fbd48b4456ab2e1fe32e0c4c74b | CC(C)(C)OC(=O)N(N)C(=O)c1ccccc1.O=C1CCC(=O)N1Cl>>CC(C)(C)OC(=O)N(NCl)C(=O)c1ccccc1 | C(C)(C)(C)OC(=O)N(N)C(C1=CC=CC=C1)=O.ClN1C(CCC1=O)=O>>C(C)(C)(C)OC(=O)N(NCl)C(C1=CC=CC=C1)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([NH2:9])[C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.O=C1CCC(=O)N1[Cl:10]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([NH:9][Cl:10])[C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | CC(C)(C)OC(=O)N(N)C(=O)c1ccccc1.O=C1CCC(=O)N1Cl | CC(C)(C)OC(=O)N(NCl)C(=O)c1ccccc1 | null | null | C(C)(=O)O.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | 5c1e0d52d03addd6eb6b1f4214099582787eed3578962faa0a1bba16dd9974fa | d6d9ae1904f6b2a8c6a1e2beda49b48f0e576035412716ace5f37cb3b01d1d12 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[C;D1;H3:2]-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[C:7](=[O;D1;H0:8])-[#7:9](-[NH2;D1;+0:10])-[C:11](=[O;D1;H0:12])-[c:13]>>[C;D1;H3:2]-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[#8:6]-[C:7](=[O;D1;H0:8])-[#7:9](-[NH;D2;+0:10]-[Cl;H0;D1;+0:1])-[C:11](=[O;D1;H0:12])-[c:13] | null | [] | null | null | 1 | HOUR | To a solution of a benzoylhydrazinecarboxylic acid tert-butyl ester (Example 7) in acetic acid (5 mL) is added N-chlorosuccinimide (1.2 eq.). After 1 hour, the reaction mixture is diluted with ethyl acetate and washed with saturated NaHCO3, water, and brine. The organic layer is dried over MgSO4 and filtered. The filtr... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine.Tertiary amide.Tertiary amide | Acylhydrazine.Acylhydrazine | C1CCNC1 | null | c1ccccc1 | HO- | C(C)(=O)O.C(C)(=O)OCC | null | 1 | CC(C)(C)OC(=O)N(N)C(=O)c1ccccc1.O=C1CCC(=O)N1Cl>C(C)(=O)O.C(C)(=O)OCC>CC(C)(C)OC(=O)N(NCl)C(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cce603932cca4abba7de902112a6eb98 | CC(C)(C)OCl.Nc1cc(F)c(F)cc1C(=O)O>>Nc1c(C(=O)O)cc(F)c(F)c1Cl | FC=1C=C(C(C(=O)O)=CC1F)N.C(C)(=O)O.C(C)(C)(C)OCl>>ClC1=C(C(C(=O)O)=CC(=C1F)F)N | CC(C)(C)O[Cl:13].[NH2:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[cH:7][c:8]([F:9])[c:10]([F:11])[cH:12]1>>[NH2:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[cH:7][c:8]([F:9])[c:10]([F:11])[c:12]1[Cl:13] | CC(C)(C)OCl.Nc1cc(F)c(F)cc1C(=O)O | Nc1c(C(=O)O)cc(F)c(F)c1Cl | null | null | ClCCl.C(C)(=O)OCC | Functional Group Interconversion | Chlorination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | C-C(-C)(-C)-O-[Cl;H0;D1;+0:1].[F;D1;H0:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](-[N;D1;H2:7]):[c:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:3](-[F;D1;H0:2]):[c:4]):[c:6](-[N;D1;H2:7]):[c:8]-[C:9](=[O;D1;H0:10])-[O;D1;H1:11] | 100.8 | [{"value": 100.8, "product": "ClC1=C(C(C(=O)O)=CC(=C1F)F)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 4,5-difluoroanthranilic acid (2.45 g, 14.2 mmol) in dichloromethane (25 mL) is added acetic acid (10 mL) and hypochlorous acid tert-butyl ester (1.75 mL, 15.6 mmol). After 2 hours, the reaction mixture is diluted with ethyl acetate and washed with water and brine. The organic layer is dried over MgSO4,... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | ClCCl.C(C)(=O)OCC | null | 2 | CC(C)(C)OCl.Nc1cc(F)c(F)cc1C(=O)O>ClCCl.C(C)(=O)OCC>Nc1c(C(=O)O)cc(F)c(F)c1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fa7df086e4e6499c96d448bcfa269c2e | CC(C)(C)OCl.Nc1cc(F)ccc1C(=O)O>>Nc1cc(F)c(Cl)cc1C(=O)O | FC=1C=C(C(C(=O)O)=CC1)N.ClOC(C)(C)C>>ClC1=C(C=C(C(C(=O)O)=C1)N)F | CC(C)(C)O[Cl:7].[NH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:8][c:9]1[C:10](=[O:11])[OH:12]>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[c:6]([Cl:7])[cH:8][c:9]1[C:10](=[O:11])[OH:12] | CC(C)(C)OCl.Nc1cc(F)ccc1C(=O)O | Nc1cc(F)c(Cl)cc1C(=O)O | null | null | ClCCl.C(C)(=O)O.C(Cl)Cl | Functional Group Interconversion | Chlorination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | C-C(-C)(-C)-O-[Cl;H0;D1;+0:1].[F;D1;H0:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]):[c:3](-[F;D1;H0:2]):[c:4] | 111.2 | [{"value": 111.2, "product": "ClC1=C(C=C(C(C(=O)O)=C1)N)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | To a solution of 4-fluoroanthranilic acid (0.882 g, 5.69 mmol) in methylene chloride (50 ML) and acetic acid (10 mL) is added tert-butyl hypochlorite (0.71 mL, 6.25 mmol) solution in dichloromethane (1 mL) dropwise over 1 minute. After 90 minutes, the reaction mixture is washed with water and brine. The organic layer i... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | ClCCl.C(C)(=O)O.C(Cl)Cl | null | 1.5 | CC(C)(C)OCl.Nc1cc(F)ccc1C(=O)O>ClCCl.C(C)(=O)O.C(Cl)Cl>Nc1cc(F)c(Cl)cc1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-af712a0070fe42688003d15eb8dd1bab | CO.O=C(O)c1cc(F)c(F)cc1NC1CC1>>COC(=O)c1cc(F)c(F)cc1NC1CC1 | C1(CC1)NC1=C(C(=O)O)C=C(C(=C1)F)F.ClCCl.CO.C[Si](C)(C)C=[N+]=[N-]>>COC(C1=C(C=C(C(=C1)F)F)NC1CC1)=O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[c:9]([F:10])[cH:11][c:12]1[NH:13][CH:14]1[CH2:15][CH2:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[c:9]([F:10])[cH:11][c:12]1[NH:13][CH:14]1[CH2:15][CH2:16]1 | CO.O=C(O)c1cc(F)c(F)cc1NC1CC1 | COC(=O)c1cc(F)c(F)cc1NC1CC1 | null | null | O.C(=O)O | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccc(NC2CC2)cc1 | 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 | 0.5 | HOUR | To a solution of 2-cyclopropylamino-4,5-difluorobenzoic acid (Example 5a) (6.0 g, 28.1 mmol), dichloromethane (100 mL), and methanol (20 mL) is added (trimethylsilyl)diazomethane (2.9 M solution in hexane) dropwise until the evolution of gas stops. The solution is stirred at room temperature for 0.5 hour and 88% formic... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1.C1CC1 | HO- | O.C(=O)O | null | 0.5 | CO.O=C(O)c1cc(F)c(F)cc1NC1CC1>O.C(=O)O>COC(=O)c1cc(F)c(F)cc1NC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bf2e5b26c85a4325b8e0f4a034dc0c42 | CCOC(=O)c1cc(F)c(F)cc1NC1CC1.O=C=NSCl>>O=c1[nH]c(=O)n(C2CC2)c2cc(F)c(F)cc12 | C(C)OC(C1=C(C=C(C(=C1)F)F)NC1CC1)=O.ClSN=C=O>>C1(CC1)N1C(NC(C2=CC(=C(C=C12)F)F)=O)=O | CCO[C:2](=[O:1])[c:17]1[c:10]([NH:6][CH:7]2[CH2:8][CH2:9]2)[cH:11][c:12]([F:13])[c:14]([F:15])[cH:16]1.ClS[N:3]=[C:4]=[O:5]>>[O:1]=[c:2]1[nH:3][c:4](=[O:5])[n:6]([CH:7]2[CH2:8][CH2:9]2)[c:10]2[cH:11][c:12]([F:13])[c:14]([F:15])[cH:16][c:17]12 | CCOC(=O)c1cc(F)c(F)cc1NC1CC1.O=C=NSCl | O=c1[nH]c(=O)n(C2CC2)c2cc(F)c(F)cc12 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | 121620ba7556cb3be25b0e31bbbe99959c37e6879059ed5927290eacc9f43c1e | 3513c98a3be17756938dbfa89da7e867549065d9a015fcc025e780b6be802c11 | O=c1[nH]c(=O)n(C2CC2)c2ccccc12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[NH;D2;+0:6]-[C:7]1-[C:8]-[C:9]-1):[c:10].Cl-S-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:11]:[c;H0;D3;+0:12](=[O;D1;H0:13]):[n;H0;D3;+0:6](-[C:7]2-[C:8]-[C:9]-2):[c:5](:[c:10]):[c:3]:1:[c:4] | 38.2 | [{"value": 38.2, "product": "C1(CC1)N1C(NC(C2=CC(=C(C=C12)F)F)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | null | null | To a solution of 2-cyclopropylamino-4,5-difluorobenzoic acid ethyl ester (Example 22) (5.0 g, 22.0 mmol) in dry dichloromethane (120 mL) under a N2 atmosphere is added chlorosulfanyl isocyanate (3.11 g, 22 mmol). The solution is reacted at room temperature for 4 hours, and the solvent is removed under reduced pressure.... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine.Monosulfide | null | c1ccccc1 | c1ccc2ncncc2c1 | C1CC1.c1ccc2ncncc2c1 | HCl | ClCCl | -20 | null | CCOC(=O)c1cc(F)c(F)cc1NC1CC1.O=C=NSCl>ClCCl>O=c1[nH]c(=O)n(C2CC2)c2cc(F)c(F)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fa49a4c2dd0b4b8eb96227f4cd80fd12 | COc1c(F)c(F)cc(C(=O)NC(=O)NC2CC2)c1F>>COc1c(F)c(F)cc2c(=O)[nH]c(=O)n(C3CC3)c12 | [NH4+].[Cl-].C1(CC1)NC(=O)NC(C1=C(C(=C(C(=C1)F)F)OC)F)=O.[H-].[Na+]>>C1(CC1)N1C(NC(C2=CC(=C(C(=C12)OC)F)F)=O)=O | F[c:19]1[c:3]([O:2][CH3:1])[c:4]([F:5])[c:6]([F:7])[cH:8][c:9]1[C:10](=[O:11])[NH:12][C:13](=[O:14])[NH:15][CH:16]1[CH2:17][CH2:18]1>>[CH3:1][O:2][c:3]1[c:4]([F:5])[c:6]([F:7])[cH:8][c:9]2[c:10](=[O:11])[nH:12][c:13](=[O:14])[n:15]([CH:16]3[CH2:17][CH2:18]3)[c:19]12 | COc1c(F)c(F)cc(C(=O)NC(=O)NC2CC2)c1F | COc1c(F)c(F)cc2c(=O)[nH]c(=O)n(C3CC3)c12 | null | null | CN(C=O)C.O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 6e75d4eb6a84e483e2ddadbb951c8da924a964b9531d8911fcf248fc4015db7e | bb4080cca4c6d1e1f6fb16e2d4c2c839a823abdb78eb7b61ba313755abab2570 | O=c1[nH]c(=O)n(C2CC2)c2ccccc12 | F-[c;H0;D3;+0:1](:[c:2](-[#8:3]):[c:4]):[c:5](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[C;H0;D3;+0:9](=[O;D1;H0:10])-[NH;D2;+0:11]-[C:12]1-[C:13]-[C:14]-1):[c:15]>>[#8:3]-[c:2](:[c:4]):[c;H0;D3;+0:1]1:[c:5](:[c:15]):[c;H0;D3;+0:6](=[O;D1;H0:7]):[nH;D2;+0:8]:[c;H0;D3;+0:9](=[O;D1;H0:10]):[n;H0;D3;+0:11]:1-[C:12]1-[C:1... | null | [] | null | null | null | null | A solution of 1-cyclopropyl-3-(3-methoxy-2,4,5-trifluorobenzoyl)urea (Example 27b, 0.94 g, 3.26 mmol) in tetrahydrofuran (20 mL) and N,N-dimethylformamide (5 mL) is treated with sodium hydride (0.275 g, 6.8 mmol, 60% in mineral oil dispersion) and heated at reflux for 16 hours. The mixture is cooled, treated with satur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Urea.Unsubstituted dicarboximide | null | c1ccccc1 | c1ccc2cncnc2c1 | c1ccc2cncnc2c1.C1CC1 | HF | CN(C=O)C.O1CCCC1 | null | null | COc1c(F)c(F)cc(C(=O)NC(=O)NC2CC2)c1F>CN(C=O)C.O1CCCC1>COc1c(F)c(F)cc2c(=O)[nH]c(=O)n(C3CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9609d165691a467a99ceed9a09f8958b | COC(=O)c1cc(F)c(F)c2c1NC(C)CO2.O=C=NS(=O)(=O)Cl>>CC1COc2c(F)c(F)cc3c(=O)[nH]c(=O)n1c23 | COC(=O)C=1C=C(C(=C2C1NC(CO2)C)F)F.ClS(=O)(=O)N=C=O.C(C)N(CC)CC>>FC=1C=C2C(NC(N3C(COC(C1F)=C32)C)=O)=O | CO[C:12]([c:11]1[cH:10][c:8]([F:9])[c:6]([F:7])[c:5]2[c:18]1[NH:17][CH:2]([CH3:1])[CH2:3][O:4]2)=[O:13].O=S(=O)(Cl)[N:14]=[C:15]=[O:16]>>[CH3:1][CH:2]1[CH2:3][O:4][c:5]2[c:6]([F:7])[c:8]([F:9])[cH:10][c:11]3[c:12](=[O:13])[nH:14][c:15](=[O:16])[n:17]1[c:18]23 | COC(=O)c1cc(F)c(F)c2c1NC(C)CO2.O=C=NS(=O)(=O)Cl | CC1COc2c(F)c(F)cc3c(=O)[nH]c(=O)n1c23 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | 91ec8e3defb45cffcf889ff90e1ccb2a57c84d5e3659baecbf62a17c20847a03 | b2e640ad6adb277738cae8a944067d998d1107d1f884bf69b59d55eb50b99f16 | O=c1[nH]c(=O)n2c3c(cccc13)OCC2 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]1:[c:6]-[#8:7]-[C:8]-[C:9](-[C;D1;H3:10])-[NH;D2;+0:11]-1.Cl-S(=O)(=O)-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[O;D1;H0:14]>>[C;D1;H3:10]-[C:9]1-[C:8]-[#8:7]-[c:6]:[c:5]2:[c:3](:[c:4]):[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:12]:[c;H0;D3;+0:13](=[O;D1;H0:14]):[n;H0;D3;+0:11]:2... | 15.9 | [{"value": 15.9, "product": "FC=1C=C2C(NC(N3C(COC(C1F)=C32)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of 1.5 g (6.2 mmol) of 7,8-difluoro-3-methyl-3,4-dihydro-2H-1,4-benzoxazine-5-carboxylic acid methyl ester (Example 32a) in 25 mL of dichloromethane is cooled to −20° C. and treated dropwise with 0.92 g (6.5 mmol) of chlorosulfonyl isocyanate. The reaction is stirred at room temperature for 18 hours and the ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | null | c1ccc2c(c1)NCCO2 | c1cc2c3c(cncn3[CH]CO2)c1 | c1cc2c3c(cncn3[CH]CO2)c1 | HCl | ClCCl | null | 18 | COC(=O)c1cc(F)c(F)c2c1NC(C)CO2.O=C=NS(=O)(=O)Cl>ClCCl>CC1COc2c(F)c(F)cc3c(=O)[nH]c(=O)n1c23 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-52f47f320e094ba2afae0887085e38a9 | COC(=O)c1cc(F)c(F)c2c1NC(C)CC2.O=C=NS(=O)(=O)Cl>>CC1CCc2c(F)c(F)cc3c(=O)[nH]c(=O)n1c23 | COC(=O)C=1C=C(C(=C2CCC(NC12)C)F)F.ClS(=O)(=O)N=C=O.C(C)(=O)[O-].[Na+].CC(C)([O-])C.[Na+]>>FC1=C(C=C2C(NC(N3C2=C1CCC3C)=O)=O)F | CO[C:12]([c:11]1[cH:10][c:8]([F:9])[c:6]([F:7])[c:5]2[c:18]1[NH:17][CH:2]([CH3:1])[CH2:3][CH2:4]2)=[O:13].O=S(=O)(Cl)[N:14]=[C:15]=[O:16]>>[CH3:1][CH:2]1[CH2:3][CH2:4][c:5]2[c:6]([F:7])[c:8]([F:9])[cH:10][c:11]3[c:12](=[O:13])[nH:14][c:15](=[O:16])[n:17]1[c:18]23 | COC(=O)c1cc(F)c(F)c2c1NC(C)CC2.O=C=NS(=O)(=O)Cl | CC1CCc2c(F)c(F)cc3c(=O)[nH]c(=O)n1c23 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | 5bd582ecfe6bc34a51834b8f636a21d51ead25d0f8a0211e2b466981179d44dc | b2e640ad6adb277738cae8a944067d998d1107d1f884bf69b59d55eb50b99f16 | O=c1[nH]c(=O)n2c3c(cccc13)CCC2 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](:[c:6])-[NH;D2;+0:7]-[C:8](-[C;D1;H3:9])-[C:10].Cl-S(=O)(=O)-[N;H0;D2;+0:11]=[C;H0;D2;+0:12]=[O;D1;H0:13]>>[C:10]-[C:8](-[C;D1;H3:9])-[n;H0;D3;+0:7]1:[c:5](:[c:6]):[c:3](:[c:4]):[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:11]:[c;H0;D3;+0:12]:1=[O;D1;H0:13] | 72.1 | [{"value": 72.1, "product": "FC1=C(C=C2C(NC(N3C2=C1CCC3C)=O)=O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 1 | HOUR | A solution of 1.07 g (4.4 mmol) of 5,6-difluoro-2-methyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (Example 32) in 25 mL of dichloromethane is cooled to −20° C. and treated dropwise with 0.85 g (6.0 mmol) of chlorosulfonyl isocyanate. The reaction is stirred at −20° C. for 1 hour, treated with 1.0 g (... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | null | c1ccc2c(c1)CCCN2 | c1cc2c3c(cncn3[CH]CC2)c1 | c1cc2c3c(cncn3[CH]CC2)c1 | HCl | ClCCl | -20 | 1 | COC(=O)c1cc(F)c(F)c2c1NC(C)CC2.O=C=NS(=O)(=O)Cl>ClCCl>CC1CCc2c(F)c(F)cc3c(=O)[nH]c(=O)n1c23 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-296269dc43554704b3f2db025bb12e66 | CCOC(=O)c1cc(F)c(SC)nc1NC1CC1.O=C=NS(=O)(=O)Cl>>CSc1nc2c(cc1F)c(=O)[nH]c(=O)n2C1CC1 | CC(C)([O-])C.[Na+].ClS(=O)(=O)N=C=O.C(C)(=O)[O-].[Na+].C1(CC1)NC1=C(C(=O)OCC)C=C(C(=N1)SC)F>>C1(CC1)N1C(NC(C2=C1N=C(C(=C2)F)SC)=O)=O | CCO[C:10]([c:6]1[c:5]([NH:15][CH:16]2[CH2:17][CH2:18]2)[n:4][c:3]([S:2][CH3:1])[c:8]([F:9])[cH:7]1)=[O:11].O=S(=O)(Cl)[N:12]=[C:13]=[O:14]>>[CH3:1][S:2][c:3]1[n:4][c:5]2[c:6]([cH:7][c:8]1[F:9])[c:10](=[O:11])[nH:12][c:13](=[O:14])[n:15]2[CH:16]1[CH2:17][CH2:18]1 | CCOC(=O)c1cc(F)c(SC)nc1NC1CC1.O=C=NS(=O)(=O)Cl | CSc1nc2c(cc1F)c(=O)[nH]c(=O)n2C1CC1 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | 5c0ad477af7d88500bf09ffb09fd74c76841c245ef9275b206c3966597586cbd | b2e640ad6adb277738cae8a944067d998d1107d1f884bf69b59d55eb50b99f16 | O=c1[nH]c(=O)n(C2CC2)c2ncccc12 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[NH;D2;+0:6]-[C:7]1-[C:8]-[C:9]-1):[#7;a:10]:[c:11].Cl-S(=O)(=O)-[N;H0;D2;+0:12]=[C;H0;D2;+0:13]=[O;D1;H0:14]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:12]:[c;H0;D3;+0:13](=[O;D1;H0:14]):[n;H0;D3;+0:6](-[C:7]2-[C:8]-[C:9]-2):[c:5](:[#7;a:10]:[c:11]):[c:3]:1:[c:4] | 18.5 | [{"value": 18.5, "product": "C1(CC1)N1C(NC(C2=C1N=C(C(=C2)F)SC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 3 | HOUR | A solution of 4.1 g (15.2 mmol) of ethyl 2-cyclopropylamino-5-fluoro-6-methylsulfanylnicotinate (Example 34) in 125 mL of dichloromethane is cooled to −20° C. and treated dropwise with 5.24 g (37 mmol) of chlorosulfonyl isocyanate. The reaction is stirred at −20° C. for 3 hours and allowed to come to room temperature o... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | null | c1ccncc1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.C1CC1 | HCl | ClCCl | -20 | 3 | CCOC(=O)c1cc(F)c(SC)nc1NC1CC1.O=C=NS(=O)(=O)Cl>ClCCl>CSc1nc2c(cc1F)c(=O)[nH]c(=O)n2C1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-185d4e0e534448e7ba4c8a2b3a5896e9 | O=[N+]([O-])c1ccc(NO)c([N+](=O)[O-])c1.O=c1[nH]c(=O)n(C2CC2)c2nc(Cl)c(F)cc12>>Nn1c(=O)c2cc(F)c(Cl)nc2n(C2CC2)c1=O | ClC=1C(=CC2=C(N(C(NC2=O)=O)C2CC2)N1)F.[H-].[Na+].[N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])NO>>NN1C(N(C2=C(C1=O)C=C(C(=N2)Cl)F)C2CC2)=O | O=[N+]([O-])c1ccc([NH:1]O)c([N+](=O)[O-])c1.[nH:2]1[c:3](=[O:4])[c:5]2[cH:6][c:7]([F:8])[c:9]([Cl:10])[n:11][c:12]2[n:13]([CH:14]2[CH2:15][CH2:16]2)[c:17]1=[O:18]>>[NH2:1][n:2]1[c:3](=[O:4])[c:5]2[cH:6][c:7]([F:8])[c:9]([Cl:10])[n:11][c:12]2[n:13]([CH:14]2[CH2:15][CH2:16]2)[c:17]1=[O:18] | O=[N+]([O-])c1ccc(NO)c([N+](=O)[O-])c1.O=c1[nH]c(=O)n(C2CC2)c2nc(Cl)c(F)cc12 | Nn1c(=O)c2cc(F)c(Cl)nc2n(C2CC2)c1=O | null | null | CN(C=O)C.O1CCOCC1 | Miscellaneous | OtherReaction | 197fc1cd782bf0a9ab124bb6694fcd605cef406f0748e8fd9b8cb146776d967a | 3bddf3a0255acf51e70359a0ac8208ce5eb2b81944f30a388fe53f3d9c8f01da | O=c1[nH]c(=O)n(C2CC2)c2ncccc12 | O-[NH;D2;+0:1]-c1:c:c:c(-[N+](=O)-[O-]):c:c:1-[N+](=O)-[O-].[#7;a:2]:[c:3]1:[c:4]:[c:5](=[O;D1;H0:6]):[nH;D2;+0:7]:[c:8](=[O;D1;H0:9]):[#7;a:10]:1-[C:11]>>[#7;a:2]:[c:3]1:[c:4]:[c:5](=[O;D1;H0:6]):[n;H0;D3;+0:7](-[NH2;D1;+0:1]):[c:8](=[O;D1;H0:9]):[#7;a:10]:1-[C:11] | 65.3 | [{"value": 65.3, "product": "NN1C(N(C2=C(C1=O)C=C(C(=N2)Cl)F)C2CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 3.83 g (15 mmol) of 7-chloro-1-cyclopropyl-6-fluoro-1H-pyrido[2,3-d]pyrimidine-2,4-dione (Example 23i) in 50 mL of dimethylformamide-dioxane (1:1) is cooled to 0° C. and treated portionwise with 0.8 g (20 mmol) of 60% sodium hydride/mineral oil. The reaction is stirred to room temperature for 30 minutes, ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group.Secondary amine | Primary amine | c1ccccc1.c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.C1CC1 | HO- | CN(C=O)C.O1CCOCC1 | null | 0.5 | O=[N+]([O-])c1ccc(NO)c([N+](=O)[O-])c1.O=c1[nH]c(=O)n(C2CC2)c2nc(Cl)c(F)cc12>CN(C=O)C.O1CCOCC1>Nn1c(=O)c2cc(F)c(Cl)nc2n(C2CC2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4df6972c6e4c48278a3fccf487f8d5a4 | O=[N+]([O-])c1ccc(NO)c([N+](=O)[O-])c1.O=c1[nH]c(=O)n(C2CC2)c2nc(S(=O)(O)=S)c(F)cc12>>Nn1c(=O)c2cc(F)c(S(=O)(O)=S)nc2n(C2CC2)c1=O | [N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])NO.C1(CC1)N1C(NC(C2=C1N=C(C(=C2)F)S(=O)(O)=S)=O)=O.[H-].[Na+]>>NN1C(N(C2=C(C1=O)C=C(C(=N2)S(=O)(O)=S)F)C2CC2)=O | O=[N+]([O-])c1ccc([NH:1]O)c([N+](=O)[O-])c1.[nH:2]1[c:3](=[O:4])[c:5]2[cH:6][c:7]([F:8])[c:9]([S:10](=[O:11])([OH:12])=[S:13])[n:14][c:15]2[n:16]([CH:17]2[CH2:18][CH2:19]2)[c:20]1=[O:21]>>[NH2:1][n:2]1[c:3](=[O:4])[c:5]2[cH:6][c:7]([F:8])[c:9]([S:10](=[O:11])([OH:12])=[S:13])[n:14][c:15]2[n:16]([CH:17]2[CH2:18][CH2:19]... | O=[N+]([O-])c1ccc(NO)c([N+](=O)[O-])c1.O=c1[nH]c(=O)n(C2CC2)c2nc(S(=O)(O)=S)c(F)cc12 | Nn1c(=O)c2cc(F)c(S(=O)(O)=S)nc2n(C2CC2)c1=O | null | null | CN(C=O)C.O1CCOCC1 | Miscellaneous | OtherReaction | 197fc1cd782bf0a9ab124bb6694fcd605cef406f0748e8fd9b8cb146776d967a | 3bddf3a0255acf51e70359a0ac8208ce5eb2b81944f30a388fe53f3d9c8f01da | O=c1[nH]c(=O)n(C2CC2)c2ncccc12 | O-[NH;D2;+0:1]-c1:c:c:c(-[N+](=O)-[O-]):c:c:1-[N+](=O)-[O-].[#7;a:2]:[c:3]1:[c:4]:[c:5](=[O;D1;H0:6]):[nH;D2;+0:7]:[c:8](=[O;D1;H0:9]):[#7;a:10]:1-[C:11]>>[#7;a:2]:[c:3]1:[c:4]:[c:5](=[O;D1;H0:6]):[n;H0;D3;+0:7](-[NH2;D1;+0:1]):[c:8](=[O;D1;H0:9]):[#7;a:10]:1-[C:11] | 76.7 | [{"value": 76.7, "product": "NN1C(N(C2=C(C1=O)C=C(C(=N2)S(=O)(O)=S)F)C2CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 0.47 g (1.57 mmol) of 1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidine-7-thiosulfonic acid (Example 35) in 20 mL of dimethylformamide/dioxane (1:1) is treated portionwise with 0.08 g (2.0 mmol) of 60% sodium hydride/mineral oil. The reaction is stirred at room temperature for 1 ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group.Secondary amine | Primary amine | c1ccccc1.c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.C1CC1 | HO- | CN(C=O)C.O1CCOCC1 | null | 1 | O=[N+]([O-])c1ccc(NO)c([N+](=O)[O-])c1.O=c1[nH]c(=O)n(C2CC2)c2nc(S(=O)(O)=S)c(F)cc12>CN(C=O)C.O1CCOCC1>Nn1c(=O)c2cc(F)c(S(=O)(O)=S)nc2n(C2CC2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9b30bb348856466e831c1ac5c92d19a5 | O=[N+]([O-])c1ccc(NO)c([N+](=O)[O-])c1.O=c1[nH]c(=O)n(C2CC2)c2cc(F)c(F)cc12>>Nn1c(=O)c2cc(F)c(F)cc2n(C2CC2)c1=O | [N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])NO.C1(CC1)N1C(NC(C2=CC(=C(C=C12)F)F)=O)=O.O1CCCC1.[H-].[Na+]>>NN1C(N(C2=CC(=C(C=C2C1=O)F)F)C1CC1)=O | O=[N+]([O-])c1ccc([NH:1]O)c([N+](=O)[O-])c1.[nH:2]1[c:3](=[O:4])[c:5]2[cH:6][c:7]([F:8])[c:9]([F:10])[cH:11][c:12]2[n:13]([CH:14]2[CH2:15][CH2:16]2)[c:17]1=[O:18]>>[NH2:1][n:2]1[c:3](=[O:4])[c:5]2[cH:6][c:7]([F:8])[c:9]([F:10])[cH:11][c:12]2[n:13]([CH:14]2[CH2:15][CH2:16]2)[c:17]1=[O:18] | O=[N+]([O-])c1ccc(NO)c([N+](=O)[O-])c1.O=c1[nH]c(=O)n(C2CC2)c2cc(F)c(F)cc12 | Nn1c(=O)c2cc(F)c(F)cc2n(C2CC2)c1=O | null | null | CN(C=O)C.O1CCOCC1 | Miscellaneous | OtherReaction | 7d9afd8ce69d2cc21587dcf7a5296320785ec57dbd2625a7e8258b9a211370fb | 3bddf3a0255acf51e70359a0ac8208ce5eb2b81944f30a388fe53f3d9c8f01da | O=c1[nH]c(=O)n(C2CC2)c2ccccc12 | O-[NH;D2;+0:1]-c1:c:c:c(-[N+](=O)-[O-]):c:c:1-[N+](=O)-[O-].[C:2]-[#7;a:3]1:[c:4]:[c:5]:[c:6](=[O;D1;H0:7]):[nH;D2;+0:8]:[c:9]:1=[O;D1;H0:10]>>[C:2]-[#7;a:3]1:[c:4]:[c:5]:[c:6](=[O;D1;H0:7]):[n;H0;D3;+0:8](-[NH2;D1;+0:1]):[c:9]:1=[O;D1;H0:10] | null | [] | 50 | CELSIUS | 25 | MINUTE | To a solution of a 1-cyclopropyl-6,7-difluoro-1H-quinazoline-2,4-dione (Example 23) in 1:1 dry tetrahydrofuran or dioxane and dry N,N-dimethylformamide is added portionwise sodium hydride (1.1 eq., 60% mineral oil dispersion) at room temperature. After stirring at 50° C. for 20 to 30 minutes, the resulting solution is ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group.Secondary amine | Primary amine | c1ccccc1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.C1CC1 | HO- | CN(C=O)C.O1CCOCC1 | 50 | 0.416667 | O=[N+]([O-])c1ccc(NO)c([N+](=O)[O-])c1.O=c1[nH]c(=O)n(C2CC2)c2cc(F)c(F)cc12>CN(C=O)C.O1CCOCC1>Nn1c(=O)c2cc(F)c(F)cc2n(C2CC2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-73b7642ecef9423da7f5d61ee74ce612 | CC(C)(C)OC(=O)N[C@H]1CCNC1.Nn1c(=O)c2cc(F)c(F)cc2n(C2CC2)c1=O>>CC(C)(C)OC(=O)N[C@H]1CCN(c2cc3c(cc2F)c(=O)n(N)c(=O)n3C2CC2)C1 | NN1C(N(C2=CC(=C(C=C2C1=O)F)F)C1CC1)=O.C(C)N(CC)CC.C(C)(C)(C)OC(N[C@@H]1CNCC1)=O>>NN1C(N(C2=CC(=C(C=C2C1=O)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)C1CC1)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][NH:12][CH2:30]1.F[c:13]1[cH:14][c:15]2[c:16]([cH:17][c:18]1[F:19])[c:20](=[O:21])[n:22]([NH2:23])[c:24](=[O:25])[n:26]2[CH:27]1[CH2:28][CH2:29]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][N:12]([c:13]2[cH... | CC(C)(C)OC(=O)N[C@H]1CCNC1.Nn1c(=O)c2cc(F)c(F)cc2n(C2CC2)c1=O | CC(C)(C)OC(=O)N[C@H]1CCN(c2cc3c(cc2F)c(=O)n(N)c(=O)n3C2CC2)C1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 7104773b13be215efb267302b4d954626cc11870e7067ef3d0293812a217ef67 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)n(C2CC2)c2cc(N3CCCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4](-[C:5]):[c:6]:[#7;a:7]:[c:8]:[c:9]:2:[c:10]:[c:11]:1-[F;D1;H0:12].[C:13]1-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[C:5]-[#7;a:4]1:[c:6]:[#7;a:7]:[c:8]:[c:9]2:[c:10]:[c:11](-[F;D1;H0:12]):[c;H0;D3;+0:1](-[N;H0;D3;+0:15]3-[C:14]-[C:13]-[C:17]-[C:16]-3):[c:2]:[c:3]:1:2 | 88.2 | [{"value": 88.2, "product": "NN1C(N(C2=CC(=C(C=C2C1=O)F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)C1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-amino-1-cyclopropyl-6,7-difluoro-1H-quinazoline-2,4-dione (Example 24a) (50.0 mg, 0.20 mmol) and triethylamine (74 mg, 0.74 mmol) in acetonitrile (3 mL) is added (S)-pyrrolidin-3-yl carbamic acid tert-butyl ester (74 mg, 0.40 mmol). The solution is refluxed for 18 hours, the solvent is removed under ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccc2ncncc2c1 | C1CC[NH]C1.c1ccc2ncncc2c1 | C1CC[NH]C1.c1ccc2ncncc2c1.C1CC1 | HF | C(C)#N | null | null | CC(C)(C)OC(=O)N[C@H]1CCNC1.Nn1c(=O)c2cc(F)c(F)cc2n(C2CC2)c1=O>C(C)#N>CC(C)(C)OC(=O)N[C@H]1CCN(c2cc3c(cc2F)c(=O)n(N)c(=O)n3C2CC2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-950eac8099204e9080cda488ff8ca284 | NC(=O)c1cc(F)c(Cl)nc1Cl.NC1CC1.O=C(Cl)C(=O)Cl>>O=C(NC(=O)c1cc(F)c(Cl)nc1Cl)NC1CC1 | C1(CC1)N.ClC1=C(C(=O)N)C=C(C(=N1)Cl)F.C(C(=O)Cl)(=O)Cl>>C1(CC1)NC(=O)NC(=O)C=1C(=NC(=C(C1)F)Cl)Cl | [NH2:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([Cl:11])[n:12][c:13]1[Cl:14].[NH2:15][CH:16]1[CH2:17][CH2:18]1.O=C(Cl)[C:2](Cl)=[O:1]>>[O:1]=[C:2]([NH:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([Cl:11])[n:12][c:13]1[Cl:14])[NH:15][CH:16]1[CH2:17][CH2:18]1 | NC(=O)c1cc(F)c(Cl)nc1Cl.NC1CC1.O=C(Cl)C(=O)Cl | O=C(NC(=O)c1cc(F)c(Cl)nc1Cl)NC1CC1 | null | null | ClCCl | Acylation | OtherReaction | e577f99702a17443c4b63368819f851a2e250f46104b0e197927714259e13f75 | 9d850324b70133759eb17211f422ea0eaaa4ed393624ec3b50fcd43d8091d8bd | O=C(NC(=O)c1cccnc1)NC1CC1 | Cl-C(=O)-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[#7;a:3]:[c:4]:[c:5]-[C:6](-[NH2;D1;+0:7])=[O;D1;H0:8].[NH2;D1;+0:9]-[C:10]1-[C:11]-[C:12]-1>>[#7;a:3]:[c:4]:[c:5]-[C:6](=[O;D1;H0:8])-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:10]1-[C:11]-[C:12]-1 | 98.5 | [{"value": 98.5, "product": "C1(CC1)NC(=O)NC(=O)C=1C(=NC(=C(C1)F)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 0.5 | HOUR | A solution of 5.8 g (27.8 mmol) of 2,6-dichloro-5-fluoronicotinamide (Chem. Pharm. Bull., 1987; 35:2280) in 60 mL of dichloromethane is treated dropwise with 5.1 g (40 mmol) of oxalyl chloride, and the reaction mixture is heated at reflux for 18 hours. The solvent is removed in vacuo, and the residue is dissolved in 50... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amide.Primary amine | Urea | null | null | c1ccncc1.C1CC1 | HCl | ClCCl | -20 | 0.5 | NC(=O)c1cc(F)c(Cl)nc1Cl.NC1CC1.O=C(Cl)C(=O)Cl>ClCCl>O=C(NC(=O)c1cc(F)c(Cl)nc1Cl)NC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d0534481b2c24568a736f1aa50104b5f | COc1c(F)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12.C[C@H](NC(=O)OC(C)(C)C)[C@@H]1CCNC1>>COc1c(N2CC[C@H]([C@@H](C)NC(=O)OC(C)(C)C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12 | NN1C(N(C2=C(C(=C(C=C2C1=O)F)F)OC)C1CC1)=O.C(C)(C)(C)OC(N[C@@H](C)[C@H]1CNCC1)=O.C(C)N(CC)CC.CS(=O)C>>C(C)(C)(C)OC(N[C@H](C)[C@@H]1CN(CC1)C1=C(C=C2C(N(C(N(C2=C1OC)C1CC1)=O)N)=O)F)=O | F[c:4]1[c:3]([O:2][CH3:1])[c:34]2[c:23]([cH:22][c:20]1[F:21])[c:24](=[O:25])[n:26]([NH2:27])[c:28](=[O:29])[n:30]2[CH:31]1[CH2:32][CH2:33]1.[NH:5]1[CH2:6][CH2:7][C@@H:8]([C@H:9]([CH3:10])[NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19]1>>[CH3:1][O:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][C@H:8]([C@@H:9... | COc1c(F)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12.C[C@H](NC(=O)OC(C)(C)C)[C@@H]1CCNC1 | COc1c(N2CC[C@H]([C@@H](C)NC(=O)OC(C)(C)C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12 | null | null | O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 7104773b13be215efb267302b4d954626cc11870e7067ef3d0293812a217ef67 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)n(C2CC2)c2cc(N3CCCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[#7;a:9](-[C:10]):[c:11]:2:[c:12]:1-[#8:13].[C:14]1-[C:15]-[C:16]-[C:17]-[NH;D2;+0:18]-1>>[#8:13]-[c:12]1:[c:11]2:[#7;a:9](-[C:10]):[c:8]:[#7;a:7]:[c:6]:[c:5]:2:[c:4]:[c:2](-[F;D1;H0:3]):[c;H0;D3;+0:1]:1-[N;H0;D3;+0:18]1-[C:14]-[C:15]-[C:16]-[C:17]... | 96.3 | [{"value": 96.3, "product": "C(C)(C)(C)OC(N[C@H](C)[C@@H]1CN(CC1)C1=C(C=C2C(N(C(N(C2=C1OC)C1CC1)=O)N)=O)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 0.57 g (2.0 mmol) of 3-amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1H-quinazoline-2,4-dione (Example 24d), 0.64 g (3.0 mmol) of ((S)-(R)-1-pyrrolidin-3-ylethyl)carbamic acid tert-butyl ester (J. Het. Chem., 1992; 29:1481), 0.81 g (8.0 mmol) of triethylamine and 10 mL of dimethyl sulfoxide is heated at 110°... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncncc2c1.C1CCNC1 | C1CC[NH]C1.c1ccc2ncncc2c1 | C1CC[NH]C1.c1ccc2ncncc2c1.C1CC1 | HF | O | null | null | COc1c(F)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12.C[C@H](NC(=O)OC(C)(C)C)[C@@H]1CCNC1>O>COc1c(N2CC[C@H]([C@@H](C)NC(=O)OC(C)(C)C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a0bbca28098c41ebaaa22e11a823a20d | C[C@H](NC(=O)OC(C)(C)C)[C@@H]1CCNC1.Cc1c(F)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12>>Cc1c(N2CC[C@H]([C@@H](C)NC(=O)OC(C)(C)C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12 | N1CCCC1.C(C)N(CC)CC.NN1C(N(C2=C(C(=C(C=C2C1=O)F)F)C)C1CC1)=O.C(C)(C)(C)OC(N[C@@H](C)[C@H]1CNCC1)=O.C(C)N(CC)CC>>C(C)(C)(C)OC(N[C@H](C)[C@@H]1CN(CC1)C1=C(C=C2C(N(C(N(C2=C1C)C1CC1)=O)N)=O)F)=O | [NH:4]1[CH2:5][CH2:6][C@@H:7]([C@H:8]([CH3:9])[NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18]1.F[c:3]1[c:2]([CH3:1])[c:33]2[c:22]([cH:21][c:19]1[F:20])[c:23](=[O:24])[n:25]([NH2:26])[c:27](=[O:28])[n:29]2[CH:30]1[CH2:31][CH2:32]1>>[CH3:1][c:2]1[c:3]([N:4]2[CH2:5][CH2:6][C@H:7]([C@@H:8]([CH3:9])[... | C[C@H](NC(=O)OC(C)(C)C)[C@@H]1CCNC1.Cc1c(F)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12 | Cc1c(N2CC[C@H]([C@@H](C)NC(=O)OC(C)(C)C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12 | null | null | CS(=O)C.O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 7104773b13be215efb267302b4d954626cc11870e7067ef3d0293812a217ef67 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)n(C2CC2)c2cc(N3CCCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[#7;a:9](-[C:10]):[c:11]:2:[c:12]:1-[C;D1;H3:13].[C:14]1-[C:15]-[C:16]-[C:17]-[NH;D2;+0:18]-1>>[C:10]-[#7;a:9]1:[c:8]:[#7;a:7]:[c:6]:[c:5]2:[c:4]:[c:2](-[F;D1;H0:3]):[c;H0;D3;+0:1](-[N;H0;D3;+0:18]3-[C:14]-[C:15]-[C:16]-[C:17]-3):[c:12](-[C;D1;H3:1... | 45.6 | [{"value": 45.6, "product": "C(C)(C)(C)OC(N[C@H](C)[C@@H]1CN(CC1)C1=C(C=C2C(N(C(N(C2=C1C)C1CC1)=O)N)=O)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A solution of 0.5 g (1.9 mmol) of 3-amino-1-cyclopropyl-6,7-difluoro-8-methyl-1H-quinazoline-2,4-dione (Example 24e), 0.64 g (3.0 mmol) of ((S)-(R)-1-pyrrolidin-3-ylethyl)carbamic acid tert-butyl ester, 0.81 g (8.0 mmol) of triethylamine and 10 mL of dimethyl sulfoxide is heated at 110° C. for 24 hours. After thin laye... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccc2ncncc2c1 | C1CC[NH]C1.c1ccc2ncncc2c1 | C1CC[NH]C1.c1ccc2ncncc2c1.C1CC1 | HF | CS(=O)C.O | 120 | null | C[C@H](NC(=O)OC(C)(C)C)[C@@H]1CCNC1.Cc1c(F)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12>CS(=O)C.O>Cc1c(N2CC[C@H]([C@@H](C)NC(=O)OC(C)(C)C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b89529cfade46778b1112e883018c13 | C[C@H](NC(=O)OC(C)(C)C)[C@H]1CCNC1.Cc1c(F)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12>>Cc1c(N2CC[C@H]([C@H](C)NC(=O)OC(C)(C)C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12 | N1CCCC1.C(C)N(CC)CC.NN1C(N(C2=C(C(=C(C=C2C1=O)F)F)C)C1CC1)=O.C(C)(C)(C)OC(N[C@@H](C)[C@@H]1CNCC1)=O.C(C)N(CC)CC>>C(C)(C)(C)OC(N[C@@H](C)[C@@H]1CN(CC1)C1=C(C=C2C(N(C(N(C2=C1C)C1CC1)=O)N)=O)F)=O | [NH:4]1[CH2:5][CH2:6][C@H:7]([C@H:8]([CH3:9])[NH:10][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:18]1.F[c:3]1[c:2]([CH3:1])[c:33]2[c:22]([cH:21][c:19]1[F:20])[c:23](=[O:24])[n:25]([NH2:26])[c:27](=[O:28])[n:29]2[CH:30]1[CH2:31][CH2:32]1>>[CH3:1][c:2]1[c:3]([N:4]2[CH2:5][CH2:6][C@H:7]([C@H:8]([CH3:9])[NH... | C[C@H](NC(=O)OC(C)(C)C)[C@H]1CCNC1.Cc1c(F)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12 | Cc1c(N2CC[C@H]([C@H](C)NC(=O)OC(C)(C)C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12 | null | null | CS(=O)C.O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 7104773b13be215efb267302b4d954626cc11870e7067ef3d0293812a217ef67 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)n(C2CC2)c2cc(N3CCCC3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[#7;a:9](-[C:10]):[c:11]:2:[c:12]:1-[C;D1;H3:13].[C:14]1-[C:15]-[C:16]-[C:17]-[NH;D2;+0:18]-1>>[C:10]-[#7;a:9]1:[c:8]:[#7;a:7]:[c:6]:[c:5]2:[c:4]:[c:2](-[F;D1;H0:3]):[c;H0;D3;+0:1](-[N;H0;D3;+0:18]3-[C:14]-[C:15]-[C:16]-[C:17]-3):[c:12](-[C;D1;H3:1... | 52.5 | [{"value": 52.5, "product": "C(C)(C)(C)OC(N[C@@H](C)[C@@H]1CN(CC1)C1=C(C=C2C(N(C(N(C2=C1C)C1CC1)=O)N)=O)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A solution of 0.5 g (1.9 mmol) of 3-amino-1-cyclopropyl-6,7-difluoro-8-methyl-1H-quinazoline-2,4-dione (Example 24e), 0.64 g (3.0 mmol) of ((S)-(S)-1-pyrrolidin-3-ylethyl)carbamic acid tert-butyl ester, 0.81 g (8.0 mmol) of triethylamine and 10 mL of dimethyl sulfoxide is heated at 110° C. for 24 hours. After thin laye... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccc2ncncc2c1 | C1CC[NH]C1.c1ccc2ncncc2c1 | C1CC[NH]C1.c1ccc2ncncc2c1.C1CC1 | HF | CS(=O)C.O | 120 | null | C[C@H](NC(=O)OC(C)(C)C)[C@H]1CCNC1.Cc1c(F)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12>CS(=O)C.O>Cc1c(N2CC[C@H]([C@H](C)NC(=O)OC(C)(C)C)C2)c(F)cc2c(=O)n(N)c(=O)n(C3CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e85e2ebb798446ffac97f400cdc25983 | CC(C)(C)OC(=O)N[C@H]1CCNC1.CC1COc2c(F)c(F)cc3c(=O)n(N)c(=O)n1c23>>CC1COc2c(N3CC[C@H](NC(=O)OC(C)(C)C)C3)c(F)cc3c(=O)n(N)c(=O)n1c23 | NN1C(N2C(COC=3C(=C(C=C(C1=O)C32)F)F)C)=O.C(C)(C)(C)OC(N[C@@H]1CNCC1)=O.C(C)N(CC)CC>>C(C)(C)(C)OC(N[C@@H]1CN(CC1)C1=C(C=C2C(N(C(N3C(COC1=C32)C)=O)N)=O)F)=O | [NH:7]1[CH2:8][CH2:9][C@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19]1.F[c:6]1[c:5]2[c:31]3[c:23]([cH:22][c:20]1[F:21])[c:24](=[O:25])[n:26]([NH2:27])[c:28](=[O:29])[n:30]3[CH:2]([CH3:1])[CH2:3][O:4]2>>[CH3:1][CH:2]1[CH2:3][O:4][c:5]2[c:6]([N:7]3[CH2:8][CH2:9][C@H:10]([NH:11][C:12](=[O:1... | CC(C)(C)OC(=O)N[C@H]1CCNC1.CC1COc2c(F)c(F)cc3c(=O)n(N)c(=O)n1c23 | CC1COc2c(N3CC[C@H](NC(=O)OC(C)(C)C)C3)c(F)cc3c(=O)n(N)c(=O)n1c23 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | da3d3dafeb9a0bcdf43850d6bbb3b56cb42f37c79a7b655b09d7a5a6d1690337 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)n2c3c(c(N4CCCC4)ccc13)OCC2 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[#7;a:9]3:[c:10]:2:[c:11]:1-[#8:12]-[C:13]-[C:14]-3.[C:15]1-[C:16]-[NH;D2;+0:17]-[C:18]-[C:19]-1>>[F;D1;H0:3]-[c:2]1:[c:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[#7;a:9]3:[c:10]:2:[c:11](:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:17]1-[C:16]-[C:15]-[C:19]-[C:18]-1)-[#8:1... | 104.1 | [{"value": 104.1, "product": "C(C)(C)(C)OC(N[C@@H]1CN(CC1)C1=C(C=C2C(N(C(N3C(COC1=C32)C)=O)N)=O)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 0.2 g (0.75 mmol) of 5-amino-8,9-difluoro-3-methyl-2,3-dihydro-1-oxa-3a,5-diazaphenalene-4,6-dione (Example 24h), 0.58 g (2.0 mmol) of (S)-3-pyrrolidinylcarbamic acid tert-butyl ester (J. Med. Chem., 1992; 35:1764), 0.5 g (0.5 mmol) of triethylamine and 20 mL of acetonitrile is heated at reflux for 18 hou... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1cc2c3c(cncn3[CH]CO2)c1 | C1CC[NH]C1.c1cc2c3c(cncn3[CH]CO2)c1 | C1CC[NH]C1.c1cc2c3c(cncn3[CH]CO2)c1 | HF | C(C)#N | null | null | CC(C)(C)OC(=O)N[C@H]1CCNC1.CC1COc2c(F)c(F)cc3c(=O)n(N)c(=O)n1c23>C(C)#N>CC1COc2c(N3CC[C@H](NC(=O)OC(C)(C)C)C3)c(F)cc3c(=O)n(N)c(=O)n1c23 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b8b2453d6ea8466d8369d3d209d68ab2 | CC1COc2c(F)c(F)cc3c(=O)n(N)c(=O)n1c23.C[C@@H](NC(=O)OC(C)(C)C)[C@H]1CCNC1>>CC1COc2c(N3CC[C@@H]([C@H](C)NC(=O)OC(C)(C)C)C3)c(F)cc3c(=O)n(N)c(=O)n1c23 | NN1C(N2C(COC=3C(=C(C=C(C1=O)C32)F)F)C)=O.C(C)(C)(C)OC(N[C@H](C)[C@@H]1CNCC1)=O.C(C)N(CC)CC>>C(C)(C)(C)OC(N[C@@H](C)[C@H]1CN(CC1)C1=C(C=C2C(N(C(N3C(COC1=C32)C)=O)N)=O)F)=O | F[c:6]1[c:5]2[c:33]3[c:25]([cH:24][c:22]1[F:23])[c:26](=[O:27])[n:28]([NH2:29])[c:30](=[O:31])[n:32]3[CH:2]([CH3:1])[CH2:3][O:4]2.[NH:7]1[CH2:8][CH2:9][C@H:10]([C@@H:11]([CH3:12])[NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21]1>>[CH3:1][CH:2]1[CH2:3][O:4][c:5]2[c:6]([N:7]3[CH2:8][CH2:9][C@@H:10]... | CC1COc2c(F)c(F)cc3c(=O)n(N)c(=O)n1c23.C[C@@H](NC(=O)OC(C)(C)C)[C@H]1CCNC1 | CC1COc2c(N3CC[C@@H]([C@H](C)NC(=O)OC(C)(C)C)C3)c(F)cc3c(=O)n(N)c(=O)n1c23 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | da3d3dafeb9a0bcdf43850d6bbb3b56cb42f37c79a7b655b09d7a5a6d1690337 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)n2c3c(c(N4CCCC4)ccc13)OCC2 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[#7;a:9]3:[c:10]:2:[c:11]:1-[#8:12]-[C:13]-[C:14]-3.[C:15]1-[C:16]-[NH;D2;+0:17]-[C:18]-[C:19]-1>>[F;D1;H0:3]-[c:2]1:[c:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[#7;a:9]3:[c:10]:2:[c:11](:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:17]1-[C:16]-[C:15]-[C:19]-[C:18]-1)-[#8:1... | 73.7 | [{"value": 73.7, "product": "C(C)(C)(C)OC(N[C@@H](C)[C@H]1CN(CC1)C1=C(C=C2C(N(C(N3C(COC1=C32)C)=O)N)=O)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 0.11 g (0.41 mmol) of 5-amino-8,9-difluoro-3-methyl-2,3-dihydro-1-oxa-3a,5-diazaphenalene-4,6-dione (Example 24h), 0.26 g (1.3 mmol) of ((R)-(S)-1-pyrrolidin-3-ylethyl)carbamic acid tert-butyl ester (J. Het. Chem., 1992; 29:1481), 0.25 g (2.5 mmol) of triethylamine and 10 mL of acetonitrile is heated at r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cc2c3c(cncn3[CH]CO2)c1.C1CCNC1 | C1CC[NH]C1.c1cc2c3c(cncn3[CH]CO2)c1 | C1CC[NH]C1.c1cc2c3c(cncn3[CH]CO2)c1 | HF | C(C)#N | null | null | CC1COc2c(F)c(F)cc3c(=O)n(N)c(=O)n1c23.C[C@@H](NC(=O)OC(C)(C)C)[C@H]1CCNC1>C(C)#N>CC1COc2c(N3CC[C@@H]([C@H](C)NC(=O)OC(C)(C)C)C3)c(F)cc3c(=O)n(N)c(=O)n1c23 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7529c8caf4b748479316487eac532aa3 | CC(C)(C)OC(=O)N[C@H]1CCNC1.CC1(N)CCc2c(F)c(F)cc3c(=O)[nH]c(=O)n1c23>>CC1CCc2c(N3CC[C@H](NC(=O)OC(C)(C)C)C3)c(F)cc3c(=O)n(N)c(=O)n1c23 | NC1(CCC=2C(=C(C=C3C(NC(N1C23)=O)=O)F)F)C.C(C)(C)(C)OC(N[C@@H]1CNCC1)=O.C(C)N(CC)CC.CS(=O)C>>C(C)(C)(C)OC(N[C@@H]1CN(CC1)C1=C(C=C2C(N(C(N3C2=C1CCC3C)=O)N)=O)F)=O | [NH:7]1[CH2:8][CH2:9][C@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19]1.F[c:6]1[c:5]2[c:31]3[c:23]([cH:22][c:20]1[F:21])[c:24](=[O:25])[nH:26][c:28](=[O:29])[n:30]3[C:2]([CH3:1])([NH2:27])[CH2:3][CH2:4]2>>[CH3:1][CH:2]1[CH2:3][CH2:4][c:5]2[c:6]([N:7]3[CH2:8][CH2:9][C@H:10]([NH:11][C:12](=... | CC(C)(C)OC(=O)N[C@H]1CCNC1.CC1(N)CCc2c(F)c(F)cc3c(=O)[nH]c(=O)n1c23 | CC1CCc2c(N3CC[C@H](NC(=O)OC(C)(C)C)C3)c(F)cc3c(=O)n(N)c(=O)n1c23 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 8b927508496a2bc8ede2a5265948ea4c2027370901c2ab699177b34dfe97a5fa | 3e73feb1dca6e66ea9b3917426713f608e758767b2fa3bbf3ea155f54ecc0d2a | O=c1[nH]c(=O)n2c3c(c(N4CCCC4)ccc13)CCC2 | F-[c;H0;D3;+0:1]1:[c:2](-[F;D1;H0:3]):[c:4]:[c:5]2:[c:6](=[O;D1;H0:7]):[nH;D2;+0:8]:[c:9](=[O;D1;H0:10]):[#7;a:11]3:[c:12]:2:[c:13]:1-[C:14]-[C:15]-[C;H0;D4;+0:16]-3(-[C;D1;H3:17])-[NH2;D1;+0:18].[C:19]1-[C:20]-[NH;D2;+0:21]-[C:22]-[C:23]-1>>[C;D1;H3:17]-[CH;D3;+0:16]1-[C:15]-[C:14]-[c:13]2:[c:12]3:[#7;a:11]-1:[c:9](=[... | 71.8 | [{"value": 71.8, "product": "C(C)(C)(C)OC(N[C@@H]1CN(CC1)C1=C(C=C2C(N(C(N3C2=C1CCC3C)=O)N)=O)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 0.12 g (0.45 mmol) of 5-amino-8,9-difluoro-5-methyl-6,7-dihydro-5H-pyrido[3,2,1-ij]quinazoline-1,3-dione (Example 24i), 0.34 g (1.8 mmol) of (S)-3-pyrrolidinylcarbamic acid tert-butyl ester (J. Med. Chem., 1992; 35:1764), 0.2 g (2.0 mmol) of triethylamine and 7 mL of dimethyl sulfoxide is heated at 110° C... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine.Secondary amine | Primary amine.Tertiary amine | C1CCNC1.C1CCc2cccc3cncn1c23 | C1CC[NH]C1.c1cc2c3c(cncn3[CH]CC2)c1 | C1CC[NH]C1.c1cc2c3c(cncn3[CH]CC2)c1 | HF | O | null | 1 | CC(C)(C)OC(=O)N[C@H]1CCNC1.CC1(N)CCc2c(F)c(F)cc3c(=O)[nH]c(=O)n1c23>O>CC1CCc2c(N3CC[C@H](NC(=O)OC(C)(C)C)C3)c(F)cc3c(=O)n(N)c(=O)n1c23 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2ab82c696e84490ebe8f5ae057f63112 | CC(C)(C)OC(=O)N[C@H]1CCNC1.Nn1c(=O)c2cc(F)c(Cl)nc2n(C2CC2)c1=O>>CC(C)(C)OC(=O)NC1CCN(c2nc3c(cc2F)c(=O)n(N)c(=O)n3C2CC2)C1 | NN1C(N(C2=C(C1=O)C=C(C(=N2)Cl)F)C2CC2)=O.C(C)(C)(C)OC(N[C@@H]1CNCC1)=O.C(C)(C)N(C(C)C)CC.C(C)#N>>C(C)(C)(C)OC(NC1CN(CC1)C=1C(=CC2=C(N(C(N(C2=O)N)=O)C2CC2)N1)F)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][NH:12][CH2:30]1.Cl[c:13]1[n:14][c:15]2[c:16]([cH:17][c:18]1[F:19])[c:20](=[O:21])[n:22]([NH2:23])[c:24](=[O:25])[n:26]2[CH:27]1[CH2:28][CH2:29]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:10][CH2:11][N:12]([c:13]2[n:1... | CC(C)(C)OC(=O)N[C@H]1CCNC1.Nn1c(=O)c2cc(F)c(Cl)nc2n(C2CC2)c1=O | CC(C)(C)OC(=O)NC1CCN(c2nc3c(cc2F)c(=O)n(N)c(=O)n3C2CC2)C1 | null | null | O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 8d4ca8461a6b23e91ba625c70adedcf11c9bf5e1ce707c6f73890ac66ced0170 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1[nH]c(=O)n(C2CC2)c2nc(N3CCCC3)ccc12 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]1-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[C:12]-[C:11]-1):[c:5](-[F;D1;H0:6]):[c:7] | 83.2 | [{"value": 83.2, "product": "C(C)(C)(C)OC(NC1CN(CC1)C=1C(=CC2=C(N(C(N(C2=O)N)=O)C2CC2)N1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A solution of 0.11 g (0.4 mmol) of 3-amino-7-chloro-1-cyclopropyl-6-fluoro-1H-pyrido[2,3-d]pyrimidine-2,4-dione (Example 24b), 0.105 g (0.56 mmol) of (S)-3-pyrrolidinylcarbamic acid tert-butyl ester (J. Med. Chem., 1992; 35:1764), 1.2 mL of N,N-diisopropylethylamine and 3 mL of acetonitrile is heated at 50° C. for 18 h... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1cnc2ncncc2c1 | C1CC[NH]C1.c1cnc2ncncc2c1 | C1CC[NH]C1.c1cnc2ncncc2c1.C1CC1 | HCl | O | 0 | null | CC(C)(C)OC(=O)N[C@H]1CCNC1.Nn1c(=O)c2cc(F)c(Cl)nc2n(C2CC2)c1=O>O>CC(C)(C)OC(=O)NC1CCN(c2nc3c(cc2F)c(=O)n(N)c(=O)n3C2CC2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7617c6a9714f4fc1badb4dccedb07ffc | C[C@@H](NC(=O)OC(C)(C)C)[C@H]1CCNC1.Nn1c(=O)c2cc(F)c(S(=O)(O)=S)nc2n(C2CC2)c1=O>>C[C@H](NC(=O)OC(C)(C)C)[C@@H]1CCN(c2nc3c(cc2F)c(=O)n(N)c(=O)n3C2CC2)C1 | NN1C(N(C2=C(C1=O)C=C(C(=N2)S(=O)(O)=S)F)C2CC2)=O.NN1C(N(C2=C(C1=O)C=C(C(=N2)S(=O)(O)=S)F)C2CC2)=O.C(C)(C)(C)OC(N[C@H](C)[C@@H]1CNCC1)=O.C(C)N(CC)CC>>C(C)(C)(C)OC(N[C@@H](C)[C@H]1CN(CC1)C=1C(=CC2=C(N(C(N(C2=O)N)=O)C2CC2)N1)F)=O | [CH3:1][C@@H:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[C@H:11]1[CH2:12][CH2:13][NH:14][CH2:32]1.O=S(O)(=S)[c:15]1[n:16][c:17]2[c:18]([cH:19][c:20]1[F:21])[c:22](=[O:23])[n:24]([NH2:25])[c:26](=[O:27])[n:28]2[CH:29]1[CH2:30][CH2:31]1>>[CH3:1][C@H:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:1... | C[C@@H](NC(=O)OC(C)(C)C)[C@H]1CCNC1.Nn1c(=O)c2cc(F)c(S(=O)(O)=S)nc2n(C2CC2)c1=O | C[C@H](NC(=O)OC(C)(C)C)[C@@H]1CCN(c2nc3c(cc2F)c(=O)n(N)c(=O)n3C2CC2)C1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 9048cbc1d11fe70a6a6f1ef740f2b1a546c5fb7a8d7b85bfb8434536f406efb7 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | O=c1[nH]c(=O)n(C2CC2)c2nc(N3CCCC3)ccc12 | O-S(=O)(=S)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]:[#7;a:4]):[c:5](-[F;D1;H0:6]):[c:7].[C:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-1>>[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[C:8]-[C:12]-1):[c:5](-[F;D1;H0:6]):[c:7] | 58.7 | [{"value": 58.7, "product": "C(C)(C)(C)OC(N[C@@H](C)[C@H]1CN(CC1)C=1C(=CC2=C(N(C(N(C2=O)N)=O)C2CC2)N1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of 0.12 g (0.38 mmol) of 3-amino-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidine-7-thiosulfonic acid (Compound 24c) in 10 mL of acetonitrile is treated with 0.24 g (1.14 mmol) of ((R)-(S)-1-pyrrolidin-3-ylethyl)carbamic acid tert-butyl ester (J. Het. Chem., 1992; 29:1481), 0.25 g ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | C1CCNC1.c1cnc2ncncc2c1 | C1CC[NH]C1.c1cnc2ncncc2c1 | C1CC[NH]C1.c1cnc2ncncc2c1.C1CC1 | Other | C(C)#N | null | 18 | C[C@@H](NC(=O)OC(C)(C)C)[C@H]1CCNC1.Nn1c(=O)c2cc(F)c(S(=O)(O)=S)nc2n(C2CC2)c1=O>C(C)#N>C[C@H](NC(=O)OC(C)(C)C)[C@@H]1CCN(c2nc3c(cc2F)c(=O)n(N)c(=O)n3C2CC2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b845dd2edd604c6ea501e182a83263a2 | CC1COc2c(ccc(F)c2F)N1.NO.OC(O)C(Cl)(Cl)Cl>>CC1COc2c(ccc(F)c2F)N1C(=O)C=NO | FC1=C(C2=C(NC(CO2)C)C=C1)F.Cl.Cl.NO.ClC(C(O)O)(Cl)Cl.O.O.O.O.O.O.O.O.O.O.S(=O)(=O)([O-])[O-].[Na+].[Na+]>>FC1=C(C2=C(N(C(CO2)C)C(C=NO)=O)C=C1)F | [CH3:1][CH:2]1[CH2:3][O:4][c:5]2[c:6]([cH:7][cH:8][c:9]([F:10])[c:11]2[F:12])[NH:13]1.[NH2:17][OH:18].O[CH:16]([C:14](Cl)(Cl)Cl)[OH:15]>>[CH3:1][CH:2]1[CH2:3][O:4][c:5]2[c:6]([cH:7][cH:8][c:9]([F:10])[c:11]2[F:12])[N:13]1[C:14](=[O:15])[CH:16]=[N:17][OH:18] | CC1COc2c(ccc(F)c2F)N1.NO.OC(O)C(Cl)(Cl)Cl | CC1COc2c(ccc(F)c2F)N1C(=O)C=NO | null | null | O | Acylation | OtherReaction | dfadd1c6df8f6d5a29d1115292936c8f1451835bff21769cf44d26ae746a2c72 | 52aca9b4c7d973694a75a6b6433690467b1da39a97cb47a62061db06e1a5716b | c1ccc2c(c1)NCCO2 | Cl-[C;H0;D4;+0:1](-Cl)(-Cl)-[CH;D3;+0:2](-O)-[OH;D1;+0:3].[C;D1;H3:4]-[C:5]1-[C:6]-[#8:7]-[c:8]:[c:9](:[c:10])-[NH;D2;+0:11]-1.[NH2;D1;+0:12]-[O;D1;H1:13]>>[C;D1;H3:4]-[C:5]1-[C:6]-[#8:7]-[c:8]:[c:9](:[c:10])-[N;H0;D3;+0:11]-1-[C;H0;D3;+0:1](=[O;H0;D1;+0:3])-[CH;D2;+0:2]=[N;H0;D2;+0:12]-[O;D1;H1:13] | null | [] | 77.5 | CELSIUS | null | null | A solution of 8.27 g (50 mmol) of chloral hydrate in 125 mL of water is treated with 112.8 g (0.35 mmol) of sodium sulfate decahydrate. The mixture is stirred and treated with a solution of 7,8-difluoro-3-methyl-3,4-dihydro-2H-benz[1,4]oxazine (Chem. Pharm. Bull., 1984; 32:4907) hydrochloride (prepared by dissolving 8.... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Secondary alcohol.Secondary alcohol.Primary amine.Secondary amine | Tertiary amide.Oxime | c1ccc2c(c1)NCCO2 | c1ccc2c(c1)[NH]CCO2 | c1ccc2c(c1)[NH]CCO2 | HCl | O | 77.5 | null | CC1COc2c(ccc(F)c2F)N1.NO.OC(O)C(Cl)(Cl)Cl>O>CC1COc2c(ccc(F)c2F)N1C(=O)C=NO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-053cc80fe9db4fb8b511eee6cdeb80be | CC1COc2c(ccc(F)c2F)N1C(=O)C=NO>>CC1COc2c(F)c(F)cc3c2N1C(=O)C3=O | FC1=C(C2=C(N(C(CO2)C)C(C=NO)=O)C=C1)F.S(O)(O)(=O)=O>>FC1=C2OCC(N3C(C(C(C=C1F)=C32)=O)=O)C | N(=[CH:16][C:14]([N:13]1[CH:2]([CH3:1])[CH2:3][O:4][c:5]2[c:6]([F:7])[c:8]([F:9])[cH:10][cH:11][c:12]21)=[O:15])[OH:17]>>[CH3:1][CH:2]1[CH2:3][O:4][c:5]2[c:6]([F:7])[c:8]([F:9])[cH:10][c:11]3[c:12]2[N:13]1[C:14](=[O:15])[C:16]3=[O:17] | CC1COc2c(ccc(F)c2F)N1C(=O)C=NO | CC1COc2c(F)c(F)cc3c2N1C(=O)C3=O | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 33b99c785a6c3c3568e3962623beb70c587545568ab3138e400dfd91fdc147c6 | ab4bf08516e66cf6fd8670ac9e8d4ecd074b35f40b66b51c2d0c9c0d98ab1c51 | O=C1C(=O)N2CCOc3cccc1c32 | [#8:1]-[c:2]:[c:3](:[cH;D2;+0:4]:[c:5]:[c:6])-[#7:7](-[C:8](=[O;D1;H0:9])-[CH;D2;+0:10]=N-[OH;D1;+0:11])-[C:12]>>[#8:1]-[c:2]:[c:3]1:[c;H0;D3;+0:4](:[c:5]:[c:6])-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[C:8](=[O;D1;H0:9])-[#7:7]-1-[C:12] | null | [] | 80 | CELSIUS | null | null | A solution of 45 mL of 98% sulfuric acid in 18 mL of water is heated to 50° C. to 60° C. and treated portionwise over 30 minutes with 10.5 g (41 mmol) of (7,8-difluoro-3-methyl-2,3-dihydro-1,4-benzoxazin-4-yl)oxoacetaldehyde oxime (Example 29). After the addition is complete, the reaction is heated to 80° C. for 15 min... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | Ketone | c1ccc2c(c1)[NH]CCO2 | c1cc2c3c(c1)OCCN3CC2 | c1cc2c3c(c1)OCCN3CC2 | Other | O | 80 | null | CC1COc2c(ccc(F)c2F)N1C(=O)C=NO>O>CC1COc2c(F)c(F)cc3c2N1C(=O)C3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4fd926229a494c629b68840a11ffe7c1 | CC1COc2c(F)c(F)cc3c2N1C(=O)C3=O.OO>>CC1COc2c(F)c(F)cc(C(=O)O)c2N1 | FC1=C2OCC(N3C(C(C(C=C1F)=C32)=O)=O)C.OO>>FC=1C(=C2C(NC(CO2)C)=C(C1)C(=O)O)F | O=C1[C:12](=[O:13])[c:11]2[cH:10][c:8]([F:9])[c:6]([F:7])[c:5]3[c:15]2[N:16]1[CH:2]([CH3:1])[CH2:3][O:4]3.O[OH:14]>>[CH3:1][CH:2]1[CH2:3][O:4][c:5]2[c:6]([F:7])[c:8]([F:9])[cH:10][c:11]([C:12](=[O:13])[OH:14])[c:15]2[NH:16]1 | CC1COc2c(F)c(F)cc3c2N1C(=O)C3=O.OO | CC1COc2c(F)c(F)cc(C(=O)O)c2N1 | null | null | [OH-].[Na+] | Acylation | OtherReaction | 331c26160f350780d6eb268d594f92792ab2a64f9a9c14591cbe111e0c7b4f03 | 74f47597d04f1974e1889dc872a1ecf734a11acc7611e0fce2bef841101f8996 | c1ccc2c(c1)NCCO2 | O-[OH;D1;+0:1].O=C1-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]2:[c:7]-[#8:8]-[C:9]-[C:10](-[C;D1;H3:11])-[N;H0;D3;+0:12]-1-2>>[C;D1;H3:11]-[C:10]1-[C:9]-[#8:8]-[c:7]:[c:6](:[c:4](-[C;H0;D3;+0:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:5])-[NH;D2;+0:12]-1 | null | [] | 5 | CELSIUS | null | null | A suspension of 6.9 g (28.8 mmol) of 6,7-difluoro-3-methyl-3,4-dihydro-5-oxa-2a-aza-acenaphthylene-1,2-dione (Example 30) in 250 mL of 4.5% aqueous sodium hydroxide is treated dropwise with 16.4 mL of 30% hydrogen peroxide over 1 hour. The reaction is filtered to remove a trace of insoluble material and the filtrate is... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Tertiary amide.Peroxide | Carboxylic acid.Secondary amine | c1cc2c3c(c1)OCCN3CC2 | c1ccc2c(c1)NCCO2 | c1ccc2c(c1)NCCO2 | Other | [OH-].[Na+] | 5 | null | CC1COc2c(F)c(F)cc3c2N1C(=O)C3=O.OO>[OH-].[Na+]>CC1COc2c(F)c(F)cc(C(=O)O)c2N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cf7993e3573e421a894de7cb83cffe3e | COC(=O)c1cc(F)c(F)c2ccc(C)nc12>>COC(=O)c1cc(F)c(F)c2c1NC(C)CC2 | COC(=O)C=1C=C(C(=C2C=CC(=NC12)C)F)F.O.[H][H]>>COC(=O)C=1C=C(C(=C2CCC(NC12)C)F)F | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[c:9]([F:10])[c:11]2[c:12]1[n:13][c:14]([CH3:15])[cH:16][cH:17]2>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[c:9]([F:10])[c:11]2[c:12]1[NH:13][CH:14]([CH3:15])[CH2:16][CH2:17]2 | COC(=O)c1cc(F)c(F)c2ccc(C)nc12 | COC(=O)c1cc(F)c(F)c2c1NC(C)CC2 | null | [Pt] | C(C)(=O)O | Reduction | OtherReaction | 0f501d7f6563b973124f46b9ac99227bf4e9d23710ef3fe61283d96ce59150d0 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | c1ccc2c(c1)CCCN2 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]1:[n;H0;D2;+0:6]:[c;H0;D3;+0:7](-[C;D1;H3:8]):[cH;D2;+0:9]:[cH;D2;+0:10]:[c:11]:1:[c:12]>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]1:[c:11](:[c:12])-[CH2;D2;+0:10]-[CH2;D2;+0:9]-[CH;D3;+0:7](-[C;D1;H3:8])-[NH;D2;+0:6]-1 | 68.9 | [{"value": 68.9, "product": "COC(=O)C=1C=C(C(=C2CCC(NC12)C)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 8.0 g (33.7 mmol) of 5,6-difluoro-2-methylquinoline-8-carboxylic acid methyl ester (Example 33) in 100 mL of glacial acetic acid is treated with 2.15 g of platinum on carbon (0.8 g of active catalyst+62.8% water) and then shaken in a hydrogen atmosphere at temperatures of 24° C. to 29° C. and pressures of... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccc2ncccc2c1 | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2 | null | [Pt].C(C)(=O)O | null | null | COC(=O)c1cc(F)c(F)c2ccc(C)nc12>[Pt].C(C)(=O)O>COC(=O)c1cc(F)c(F)c2c1NC(C)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2f6822f4b3d84e5c8faab5b8723b6257 | CCOC(=O)c1cc(F)c(SC)nc1Cl.NC1CC1>>CCOC(=O)c1cc(F)c(SC)nc1NC1CC1 | C(C)OC(C1=C(N=C(C(=C1)F)SC)Cl)=O.C1(CC1)N.C1(CC1)N>>C(C)OC(C1=C(N=C(C(=C1)F)SC)NC1CC1)=O | Cl[c:14]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][c:8]([F:9])[c:10]([S:11][CH3:12])[n:13]1.[NH2:15][CH:16]1[CH2:17][CH2:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([F:9])[c:10]([S:11][CH3:12])[n:13][c:14]1[NH:15][CH:16]1[CH2:17][CH2:18]1 | CCOC(=O)c1cc(F)c(SC)nc1Cl.NC1CC1 | CCOC(=O)c1cc(F)c(SC)nc1NC1CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(NC2CC2)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8]):[c:9].[NH2;D1;+0:10]-[C:11]1-[C:12]-[C:13]-1>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:10]-[C:11]1-[C:12]-[C:13]-1):[#7;a:2]:[c:3] | 69.1 | [{"value": 69.1, "product": "C(C)OC(C1=C(N=C(C(=C1)F)SC)NC1CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 8.7 g (34.8 mmol) of 2-chloro-5-fluoro-6-methylsulfanylnicotinic acid ethyl ester (J. Med. Chem., 1993; 36:2676) and 5.7 g (100 mmol) of cyclopropylamine in 100 mL of acetonitrile is heated at reflux for 18 hours. After TLC showed the presence of unreacted starting material, 4.12 g (72 mmol) of cyclopropy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CC1 | HCl | C(C)#N | null | null | CCOC(=O)c1cc(F)c(SC)nc1Cl.NC1CC1>C(C)#N>CCOC(=O)c1cc(F)c(SC)nc1NC1CC1 |
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