dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac6f378a36264ca09a05c3888f6890ed | CCOc1ncnc2ccc(C=O)cc12.O=C1CSC(NCCc2cccc(F)c2)=N1>>CCOc1ncnc2ccc(/C=C3\SC(NCCc4cccc(F)c4)=NC3=O)cc12 | C(C)OC1=NC=NC2=CC=C(C=C12)C=O.FC=1C=C(C=CC1)CCNC=1SCC(N1)=O.N1CCCCC1>>C(C)OC1=NC=NC2=CC=C(C=C12)\C=C/1\C(N=C(S1)NCCC1=CC(=CC=C1)F)=O | O=[CH:12][c:11]1[cH:10][cH:9][c:8]2[n:7][cH:6][n:5][c:4]([O:3][CH2:2][CH3:1])[c:30]2[cH:29]1.[CH2:13]1[S:14][C:15]([NH:16][CH2:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][c:23]([F:24])[cH:25]2)=[N:26][C:27]1=[O:28]>>[CH3:1][CH2:2][O:3][c:4]1[n:5][cH:6][n:7][c:8]2[cH:9][cH:10][c:11](/[CH:12]=[C:13]3\[S:14][C:15]([NH:16][CH2... | CCOc1ncnc2ccc(C=O)cc12.O=C1CSC(NCCc2cccc(F)c2)=N1 | CCOc1ncnc2ccc(/C=C3\SC(NCCc4cccc(F)c4)=NC3=O)cc12 | null | null | C(C)O | C-C Coupling | Aldol condensation | 269ab2e573a3c091a52ebc4e3efbf6cfa420243fb0cbe3e1b0cb45b4df823f3b | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1N=C(NCCc2ccccc2)S/C1=C\c1ccc2ncncc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]=[C:8]-[#16:9]-[CH2;D2;+0:10]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]=[C:8]-[#16:9]/[C;H0;D3;+0:10]-1=[CH;D2;+0:1]\[c:2](:[c:3]):[c:4] | 30 | [{"value": 30.0, "product": "C(C)OC1=NC=NC2=CC=C(C=C12)\\C=C/1\\C(N=C(S1)NCCC1=CC(=CC=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.4, "product": "C(C)OC1=NC=NC2=CC=C(C=C12)\\C=C/1\\C(N=C(S1)NCCC1=CC(=CC=C1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The mixture of 4-ethoxy-quinazoline-6-carbaldehyde (example 10b, 20 mg, 0.1 mmol,), 2-[2-(3-Fluoro-phenyl)-ethylamino]-thiazol-4-one (example 10c, 24 mg, 0.1 mmol) and piperidine (10 ul, 0.1 mmol) in anhydrous ethyl alcohol (1 ml) was microwaved at 160° C. for 25 min. After cooling the reaction to room temperature, the... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1=NCCS1 | C1=NCCS1 | c1ccc2ncncc2c1.C1=NCCS1.c1ccccc1 | HO- | C(C)O | null | null | CCOc1ncnc2ccc(C=O)cc12.O=C1CSC(NCCc2cccc(F)c2)=N1>C(C)O>CCOc1ncnc2ccc(/C=C3\SC(NCCc4cccc(F)c4)=NC3=O)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8533b7a9ee9c407d98002ffd5212a1ef | CCOc1ncnc2ccc(C=O)cc12.COc1ccc(/C=C2\SC(=N)NC2=O)cc1OC1CCCC1>>CCOc1ncnc2ccc(/C=C3\SC(N)=NC3=O)cc12 | O.C(C)OC1=NC=NC2=CC=C(C=C12)C=O.COC=1C=CC(=CC1OC2CCCC2)/C=C\3/C(=O)NC(=N)S3.C(C)(=O)[O-].[Na+]>>NC=1S\C(\C(N1)=O)=C/C=1C=C2C(=NC=NC2=CC1)OCC | O=C[c:11]1[cH:10][cH:9][c:8]2[n:7][cH:6][n:5][c:4]([O:3][CH2:2][CH3:1])[c:21]2[cH:20]1.COc1ccc(/[CH:12]=[C:13]2\[S:14][C:15](=[NH:16])[NH:17][C:18]2=[O:19])cc1OC1CCCC1>>[CH3:1][CH2:2][O:3][c:4]1[n:5][cH:6][n:7][c:8]2[cH:9][cH:10][c:11](/[CH:12]=[C:13]3\[S:14][C:15]([NH2:16])=[N:17][C:18]3=[O:19])[cH:20][c:21]12 | CCOc1ncnc2ccc(C=O)cc12.COc1ccc(/C=C2\SC(=N)NC2=O)cc1OC1CCCC1 | CCOc1ncnc2ccc(/C=C3\SC(N)=NC3=O)cc12 | null | null | C(C)(=O)O | C-C Coupling | OtherReaction | 39cab3c4e7b3801c04d84b8d81e0bf02976d89d4417be7fffecbf82d4d69498d | 465c72fd7a2f8cddd3fe67ca188cc7da561e9bea7e014364b7550acaac0d730e | O=C1N=CS/C1=C\c1ccc2ncncc2c1 | C-O-c1:c:c:c(/[CH;D2;+0:1]=[C:2]2\[#16:3]-[C;H0;D3;+0:4](=[NH;D1;+0:5])-[NH;D2;+0:6]-[C:7]-2=[O;D1;H0:8]):c:c:1-O-C1-C-C-C-C-1.O=C-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12](:[#7;a:13]):[c:14](:[c:15]:1):[c:16]:[#7;a:17]>>[#7;a:17]:[c:16]:[c:14]1:[c:15]:[c;H0;D3;+0:9](/[CH;D2;+0:1]=[C:2]2\[#16:3]-[C;H0;D3;+0:4](-[NH2;D1;+0:5... | null | [] | null | null | null | null | The suspension of 4-ethoxy-quinazoline-6-carbaldehyde (example 10b) (1 equiv.), pseudothiohydantoin (1 equiv.), and sodium acetate (4 equiv.) in acetic acid was stirred under reflux for 12 h. After cooling to room temperature, water was added. The solid was collected by filtration, washed with water and dried to 2-amin... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Ether.Secondary amide.Monosulfide | Primary amine.Monosulfide | c1ccc2ncncc2c1.c1ccccc1.C1CSCN1.C1CCCC1 | c1ccc2ncncc2c1.C1=NCCS1 | c1ccc2ncncc2c1.C1=NCCS1 | HO- | C(C)(=O)O | null | null | CCOc1ncnc2ccc(C=O)cc12.COc1ccc(/C=C2\SC(=N)NC2=O)cc1OC1CCCC1>C(C)(=O)O>CCOc1ncnc2ccc(/C=C3\SC(N)=NC3=O)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ed5d8e8822e446090d4f49b7e4e1721 | N[C@@H]1C[C@H]1c1ccccc1.O=C1CSC(=S)N1>>O=C1CSC(N[C@@H]2C[C@H]2c2ccccc2)=N1 | CCN(C(C)C)C(C)C.C1(=CC=CC=C1)[C@H]1[C@@H](C1)N.S1C(=S)NC(=O)C1>>C1(=CC=CC=C1)[C@H]1[C@@H](C1)NC=1SCC(N1)=O | [NH2:6][C@@H:7]1[CH2:8][C@H:9]1[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.S=[C:5]1[S:4][CH2:3][C:2](=[O:1])[NH:16]1>>[O:1]=[C:2]1[CH2:3][S:4][C:5]([NH:6][C@@H:7]2[CH2:8][C@H:9]2[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)=[N:16]1 | N[C@@H]1C[C@H]1c1ccccc1.O=C1CSC(=S)N1 | O=C1CSC(N[C@@H]2C[C@H]2c2ccccc2)=N1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 064ec4f4c9b054f21155524d05c8912d1c47d6f5ce3afcc6942dcefbbf4c33bd | 084147ade391ce0e1f4741b2f27289756f43b75fc8236974db260253a45beca1 | O=C1CSC(N[C@@H]2C[C@H]2c2ccccc2)=N1 | S=[C;H0;D3;+0:1]1-[#16:2]-[C:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-1.[NH2;D1;+0:7]-[C:8]1-[C:9]-[C:10]-1>>[O;D1;H0:5]=[C:4]1-[C:3]-[#16:2]-[C;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]2-[C:9]-[C:10]-2)=[N;H0;D2;+0:6]-1 | null | [] | null | null | null | null | Similar procedure as described in example 10c was used, starting with (1R,2S)-2-phenyl-cyclopropylamine, rhodanine, mercuric chloride and DIEA to give 2-((1R,2S)-2-phenyl-cyclopropylamino)-thiazol-4-one. LC-MS m/e 232 (MH+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Thioamide.Secondary amide.Primary amine | Secondary amine.Monosulfide | C1CSCN1 | C1=NCCS1 | C1=NCCS1.C1CC1.c1ccccc1 | Other | null | null | null | N[C@@H]1C[C@H]1c1ccccc1.O=C1CSC(=S)N1>>O=C1CSC(N[C@@H]2C[C@H]2c2ccccc2)=N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6119456a886f44c8a859bfe7ffa6b0aa | Nc1ccc(Br)cc1C(=O)O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>>O=c1[nH]c2ccc(Br)cc2c(=O)o1 | ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl.N1=CC=CC=C1.NC1=C(C(=O)O)C=C(C=C1)Br>>BrC1=CC2=C(NC(OC2=O)=O)C=C1 | [NH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]1[C:11](=[O:12])[OH:13].ClC(Cl)(Cl)O[C:2](OC(Cl)(Cl)Cl)=[O:1]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][cH:6][c:7]([Br:8])[cH:9][c:10]2[c:11](=[O:12])[o:13]1 | Nc1ccc(Br)cc1C(=O)O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl | O=c1[nH]c2ccc(Br)cc2c(=O)o1 | null | null | ClCCl.C(C)#N | Aromatic Heterocycle Formation | OtherReaction | 4438482a7765163ba9d908bbdbc37c70f8a9bf9510d00368919b1c212294e061 | 978aee14c5a6c161c15b14d8af7d43f564770f634ab8a62eec842fdff80e6ac1 | O=c1[nH]c2ccccc2c(=O)o1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[OH;D1;+0:9]):[c:10]>>[O;D1;H0:8]=[c;H0;D3;+0:7]1:[o;H0;D2;+0:9]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:3]:[c:4](:[c:5]):[c:6]:1:[c:10] | 277.6 | [{"value": 93.0, "product": "BrC1=CC2=C(NC(OC2=O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 277.6, "product": "BrC1=CC2=C(NC(OC2=O)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 2-amino-5-bromo-benzoic acid (270 g, 1.25 mol) in acetonitrile (1250 mL) was added a solution of triphosgene (123.8 g, 416.7 mmol) in dichloromethane (DCM) (500 mL) and pyridine (197.5 g, 2.5 mol) simultaneously at 55° C. The resultant mixture was stirred for another 3 hours then cooled to room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Carboxylic acid.Primary amine | null | c1ccccc1 | c1ccc2ncocc2c1 | c1ccc2ncocc2c1 | HCl | ClCCl.C(C)#N | null | null | Nc1ccc(Br)cc1C(=O)O.O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl>ClCCl.C(C)#N>O=c1[nH]c2ccc(Br)cc2c(=O)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb105baebc4d4924b7b9b2c6c3bd8a2b | CNC(=N)SC.O=c1[nH]c2ccc(Br)cc2c(=O)o1>>CNc1nc(=O)c2cc(Br)ccc2[nH]1 | C([O-])([O-])=O.[Na+].[Na+].C(C)#N.BrC1=CC2=C(NC(OC2=O)=O)C=C1.CNC(SC)=N>>BrC=1C=C2C(N=C(NC2=CC1)NC)=O | CS[C:3]([NH:2][CH3:1])=[NH:4].O=c1o[c:5](=[O:6])[c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]2[nH:14]1>>[CH3:1][NH:2][c:3]1[n:4][c:5](=[O:6])[c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]2[nH:14]1 | CNC(=N)SC.O=c1[nH]c2ccc(Br)cc2c(=O)o1 | CNc1nc(=O)c2cc(Br)ccc2[nH]1 | null | null | O | Miscellaneous | OtherReaction | ff7f58ace9a104eb536c73d093925b800783331f6b321efacd4d24c23e524d1e | 64c541a76fd0ac6213d2fb5a2cc9d5505fa77e9af49a5bef8f7d5e31c19ebf30 | O=c1nc[nH]c2ccccc12 | C-S-[C;H0;D3;+0:1](=[NH;D1;+0:2])-[#7:3]-[C;D1;H3:4].O=c1:[nH;D2;+0:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:10](=[O;D1;H0:11]):o:1>>[C;D1;H3:4]-[#7:3]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:10](=[O;D1;H0:11]):[c:8](:[c:9]):[c:6](:[c:7]):[nH;D2;+0:5]:1 | 65 | [{"value": 65.0, "product": "BrC=1C=C2C(N=C(NC2=CC1)NC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a combined solution of acetonitrile (360 mL) and water (90 mL) was added 6-bromo-1H-benzo[d][1,3]oxazine-2,4-dione (24.2 g, 0.1 mol), 1,2-dimethyl-isothiourea hydriodic (23.2 g, 0.1 mol) followed by anhydrous sodium carbonate (11.7 g, 0.11 mol) and the mixture was heated to reflux for 3 hours. After cooling down, th... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | null | c1ccc2ncocc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | Other | O | null | null | CNC(=N)SC.O=c1[nH]c2ccc(Br)cc2c(=O)o1>O>CNc1nc(=O)c2cc(Br)ccc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ddb59a057d7a443dbf04b121b69d6a62 | CNc1nc(=O)c2cc(Br)ccc2[nH]1.O=P(Cl)(Cl)Cl>>CNc1nc(Cl)c2cc(Br)ccc2n1 | CN(C1=CC=CC=C1)C.BrC=1C=C2C(N=C(NC2=CC1)NC)=O.P(=O)(Cl)(Cl)Cl.[OH-].[Na+]>>BrC=1C=C2C(=NC(=NC2=CC1)NC)Cl | O=[c:5]1[n:4][c:3]([NH:2][CH3:1])[nH:14][c:13]2[c:7]1[cH:8][c:9]([Br:10])[cH:11][cH:12]2.O=P(Cl)(Cl)[Cl:6]>>[CH3:1][NH:2][c:3]1[n:4][c:5]([Cl:6])[c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]2[n:14]1 | CNc1nc(=O)c2cc(Br)ccc2[nH]1.O=P(Cl)(Cl)Cl | CNc1nc(Cl)c2cc(Br)ccc2n1 | null | null | null | Functional Group Interconversion | OtherReaction | 3788560e87eee8765e749543914a91a512631307b97fad163ebef894d2a0ea68 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ncncc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[#7;a:3]:[c:4](-[#7:5]):[nH;D2;+0:6]:[c:7](:[c:8]):[c:9]:1:[c:10]>>[#7:5]-[c:4]1:[#7;a:3]:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[c:9](:[c:10]):[c:7](:[c:8]):[n;H0;D2;+0:6]:1 | 46.6 | [{"value": 46.6, "product": "BrC=1C=C2C(=NC(=NC2=CC1)NC)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of phosphorus oxychloride (50 mL) was added powdered 6-bromo-2-methylamino-1H-quinazolin-4-one (10.0 g, 39.4 mmol) followed by dimethyl-phenyl-amine (8 mL) and the mixture was heated to reflux under N2 atmosphere for half an hour. After cooling down, the mixture was poured onto ice and basified with aqueo... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HCl | null | null | null | CNc1nc(=O)c2cc(Br)ccc2[nH]1.O=P(Cl)(Cl)Cl>>CNc1nc(Cl)c2cc(Br)ccc2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f060ebdb7bd541b3a7c86c1fbdefc008 | CC[O-].CNc1nc(Cl)c2cc(Br)ccc2n1>>CCOc1nc(NC)nc2ccc(Br)cc12 | [O-]CC.[Na+].BrC=1C=C2C(=NC(=NC2=CC1)NC)Cl>>BrC=1C=C2C(=NC(=NC2=CC1)NC)OCC | [CH3:1][CH2:2][O-:3].Cl[c:4]1[n:5][c:6]([NH:7][CH3:8])[n:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]12>>[CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]([NH:7][CH3:8])[n:9][c:10]2[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]12 | CC[O-].CNc1nc(Cl)c2cc(Br)ccc2n1 | CCOc1nc(NC)nc2ccc(Br)cc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b3369511118a10d7d701b55617dec1e99d233682c3e2c9839106d2edd5e7154d | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1ccc2ncncc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[C;D1;H3:9]-[C:10]-[O-;H0;D1:11]>>[C;D1;H3:9]-[C:10]-[O;H0;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8] | 29.8 | [{"value": 29.8, "product": "BrC=1C=C2C(=NC(=NC2=CC1)NC)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.8, "product": "BrC=1C=C2C(=NC(=NC2=CC1)NC)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of sodium ethoxide (8.11 g, 119.3 mmol) in absolute alcohol (150 mL) was added powder (6-bromo-4-chloro-quinazolin-2-yl)-methyl-amine (13 g, 47.7 mmol) in one portion and the mixture was stirred for 3 hours at room temperature under N2 atmosphere. The excess of alcohol was removed in vacuo and the residue... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | Other | null | null | 3 | CC[O-].CNc1nc(Cl)c2cc(Br)ccc2n1>>CCOc1nc(NC)nc2ccc(Br)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d50480a27e734a2ca3c9743866018e63 | CCOc1nc(NC)nc2ccc(Br)cc12>>CCOc1nc(NC)nc2ccc(C=O)cc12 | BrC=1C=C2C(=NC(=NC2=CC1)NC)OCC.C(C)#N.CS(=O)C.C(=O)[O-].[Na+]>>C(C)OC1=NC(=NC2=CC=C(C=C12)C=O)NC | Br[c:13]1[cH:12][cH:11][c:10]2[n:9][c:6]([NH:7][CH3:8])[n:5][c:4]([O:3][CH2:2][CH3:1])[c:17]2[cH:16]1>>[CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]([NH:7][CH3:8])[n:9][c:10]2[cH:11][cH:12][c:13]([CH:14]=[O:15])[cH:16][c:17]12 | CCOc1nc(NC)nc2ccc(Br)cc12 | CCOc1nc(NC)nc2ccc(C=O)cc12 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O | Oxidation | OtherReaction | e53ab74e2bb75782cbcfd1829b902e03eb16583a37234800ac88e85646ec8ded | c25c3c47812a3895da25740aba48490812213ba83ecb1b4955751c5b0488c20c | c1ccc2ncncc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[c:7]:1):[c:8]:[#7;a:9]>>[#7;a:9]:[c:8]:[c:6]1:[c:7]:[c;H0;D3;+0:1](-[C:10]=[O;D1;H0:11]):[c:2]:[c:3]:[c:4]:1:[#7;a:5] | 30.1 | [{"value": 30.0, "product": "C(C)OC1=NC(=NC2=CC=C(C=C12)C=O)NC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.1, "product": "C(C)OC1=NC(=NC2=CC=C(C=C12)C=O)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | To a combined solution of acetonitrile (40 mL) and DMSO (40 mL) was added tetrakis(triphenylphosphine)palladium(0) (1.65 g, 1.43 mmol), anhydrous sodium formate (5.82 g, 85.6 mmol) followed by powder (6-bromo-4-ethoxy-quinazolin-2-yl)-methyl-amine (4 g, 14.3 mmol) and the resultant mixture was heated to 85° C., 50 psi ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aldehyde | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | Br- | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O | null | 48 | CCOc1nc(NC)nc2ccc(Br)cc12>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O>CCOc1nc(NC)nc2ccc(C=O)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-160243ad90a7412693e3a5dd49a9d7f0 | NCc1ccccc1Cl.O=C1CSC(=S)N1>>O=C1CSC(NCc2ccccc2Cl)=N1 | CCN(C(C)C)C(C)C.ClC1=C(CN)C=CC=C1.S1C(=S)NC(=O)C1>>ClC1=C(CNC=2SCC(N2)=O)C=CC=C1 | [NH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[Cl:14].S=[C:5]1[S:4][CH2:3][C:2](=[O:1])[NH:15]1>>[O:1]=[C:2]1[CH2:3][S:4][C:5]([NH:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[Cl:14])=[N:15]1 | NCc1ccccc1Cl.O=C1CSC(=S)N1 | O=C1CSC(NCc2ccccc2Cl)=N1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 064ec4f4c9b054f21155524d05c8912d1c47d6f5ce3afcc6942dcefbbf4c33bd | 084147ade391ce0e1f4741b2f27289756f43b75fc8236974db260253a45beca1 | O=C1CSC(NCc2ccccc2)=N1 | S=[C;H0;D3;+0:1]1-[#16:2]-[C:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-1.[NH2;D1;+0:7]-[C:8]-[c:9]>>[O;D1;H0:5]=[C:4]1-[C:3]-[#16:2]-[C;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[c:9])=[N;H0;D2;+0:6]-1 | null | [] | null | null | null | null | Similar procedure as described in example 10c was used, starting with 2-chloro-benzylamine, rhodanine, mercuric chloride and DIEA to give 2-(2-chloro-benzylamino)-thiazol-4-one. LC-MS m/e 241 (MH+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Thioamide.Secondary amide.Primary amine | Secondary amine.Monosulfide | C1CSCN1 | C1=NCCS1 | C1=NCCS1.c1ccccc1 | Other | null | null | null | NCc1ccccc1Cl.O=C1CSC(=S)N1>>O=C1CSC(NCc2ccccc2Cl)=N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d6e2ca4977c14602ad60670b8cba3b6b | CCOc1nc(NC)nc2ccc(C=O)cc12.O=C1CSC(NCc2ccccc2Cl)=N1>>CCOc1nc(NC)nc2ccc(C=C3SC(NCc4ccccc4Cl)=NC3=O)cc12 | ClC1=C(CNC=2SCC(N2)=O)C=CC=C1.C(C)OC1=NC(=NC2=CC=C(C=C12)C=O)NC.C(C1=CC=CC=C1)(=O)O.N1CCCCC1>>ClC1=C(CNC=2SC(C(N2)=O)=CC=2C=C3C(=NC(=NC3=CC2)NC)OCC)C=CC=C1 | O=[CH:14][c:13]1[cH:12][cH:11][c:10]2[n:9][c:6]([NH:7][CH3:8])[n:5][c:4]([O:3][CH2:2][CH3:1])[c:31]2[cH:30]1.[CH2:15]1[S:16][C:17]([NH:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[Cl:26])=[N:27][C:28]1=[O:29]>>[CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]([NH:7][CH3:8])[n:9][c:10]2[cH:11][cH:12][c:13]([CH:14]=[C:15]3[S:... | CCOc1nc(NC)nc2ccc(C=O)cc12.O=C1CSC(NCc2ccccc2Cl)=N1 | CCOc1nc(NC)nc2ccc(C=C3SC(NCc4ccccc4Cl)=NC3=O)cc12 | null | null | C1(=CC=CC=C1)C | C-C Coupling | Aldol condensation | 269ab2e573a3c091a52ebc4e3efbf6cfa420243fb0cbe3e1b0cb45b4df823f3b | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1N=C(NCc2ccccc2)SC1=Cc1ccc2ncncc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]=[C:8]-[#16:9]-[CH2;D2;+0:10]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]=[C:8]-[#16:9]-[C;H0;D3;+0:10]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 150 | CELSIUS | null | null | To a suspension of 2-(2-chloro-benzylamino)-thiazol-4-one (example 13a, 38.5. mg, 0.16 mmole), and 4-ethoxy-2-methylamino-quinazoline-6-carbaldehyde (example 12f, 45.5 mg, 0.20 mmole) in 2 mL of toluene in a microwave tube were added benzoic acid (2.0 mg, 0.016 mmole) and piperidine (1.5 mg, 0.02 mmole). The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1=NCCS1 | C1=NCCS1 | c1ccc2ncncc2c1.C1=NCCS1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | 150 | null | CCOc1nc(NC)nc2ccc(C=O)cc12.O=C1CSC(NCc2ccccc2Cl)=N1>C1(=CC=CC=C1)C>CCOc1nc(NC)nc2ccc(C=C3SC(NCc4ccccc4Cl)=NC3=O)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa6831f0a5fb436195e70ba8fb5525d5 | Cc1ccsc1CN.O=C1CSC(=S)N1>>Cc1ccsc1CNC1=NC(=O)CS1 | CC1=C(SC=C1)CN.S1C(=S)NC(=O)C1.C(C)(C)N(CC)C(C)C>>CC1=C(SC=C1)CNC=1SCC(N1)=O | [CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1[CH2:7][NH2:8].S=[C:9]1[NH:10][C:11](=[O:12])[CH2:13][S:14]1>>[CH3:1][c:2]1[cH:3][cH:4][s:5][c:6]1[CH2:7][NH:8][C:9]1=[N:10][C:11](=[O:12])[CH2:13][S:14]1 | Cc1ccsc1CN.O=C1CSC(=S)N1 | Cc1ccsc1CNC1=NC(=O)CS1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 064ec4f4c9b054f21155524d05c8912d1c47d6f5ce3afcc6942dcefbbf4c33bd | 084147ade391ce0e1f4741b2f27289756f43b75fc8236974db260253a45beca1 | O=C1CSC(NCc2cccs2)=N1 | S=[C;H0;D3;+0:1]1-[#16:2]-[C:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-1.[#16;a:7]:[c:8]-[C:9]-[NH2;D1;+0:10]>>[#16;a:7]:[c:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1]1=[N;H0;D2;+0:6]-[C:4](=[O;D1;H0:5])-[C:3]-[#16:2]-1 | 31.5 | [{"value": 31.5, "product": "CC1=C(SC=C1)CNC=1SCC(N1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.3, "product": "CC1=C(SC=C1)CNC=1SCC(N1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | DAY | To a solution of 3-methyl-thiophen-2-ylmethylamine (700 mg, 5.5 mmol) and rhodanine (732 mg, 5.5 mmol) in acetonitrile (30 mL) was added diisopropylethylamine (DIEA) (1.91 mL, 11 mmol) at room temperature. Then, this solution was cooled to 0° C. and mercuric chloride (1.52 g, 5.6 mmol) was added in one portion. After a... | 10.6084/m9.figshare.5104873.v1 | null | Thioamide.Secondary amide.Primary amine | Secondary amine.Monosulfide | C1CSCN1 | C1=NCCS1 | c1ccsc1.C1=NCCS1 | Other | C(C)#N | 0 | 72 | Cc1ccsc1CN.O=C1CSC(=S)N1>C(C)#N>Cc1ccsc1CNC1=NC(=O)CS1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eecd9b28c4a9488cac0498959b85a29f | CCOc1nc(NC)nc2ccc(C=O)cc12.Cc1ccsc1CNC1=NC(=O)CS1>>CCOc1nc(NC)nc2ccc(C=C3SC(NCc4sccc4C)=NC3=O)cc12 | CC1=C(SC=C1)CNC=1SCC(N1)=O.C(C)OC1=NC(=NC2=CC=C(C=C12)C=O)NC.C(C1=CC=CC=C1)(=O)O.N1CCCCC1>>C(C)OC1=NC(=NC2=CC=C(C=C12)C=C1C(N=C(S1)NCC=1SC=CC1C)=O)NC | O=[CH:14][c:13]1[cH:12][cH:11][c:10]2[n:9][c:6]([NH:7][CH3:8])[n:5][c:4]([O:3][CH2:2][CH3:1])[c:30]2[cH:29]1.[CH2:15]1[S:16][C:17]([NH:18][CH2:19][c:20]2[s:21][cH:22][cH:23][c:24]2[CH3:25])=[N:26][C:27]1=[O:28]>>[CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]([NH:7][CH3:8])[n:9][c:10]2[cH:11][cH:12][c:13]([CH:14]=[C:15]3[S:16][C:1... | CCOc1nc(NC)nc2ccc(C=O)cc12.Cc1ccsc1CNC1=NC(=O)CS1 | CCOc1nc(NC)nc2ccc(C=C3SC(NCc4sccc4C)=NC3=O)cc12 | null | null | C1(=CC=CC=C1)C | C-C Coupling | Aldol condensation | 269ab2e573a3c091a52ebc4e3efbf6cfa420243fb0cbe3e1b0cb45b4df823f3b | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1N=C(NCc2cccs2)SC1=Cc1ccc2ncncc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]=[C:8]-[#16:9]-[CH2;D2;+0:10]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]=[C:8]-[#16:9]-[C;H0;D3;+0:10]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 150 | CELSIUS | null | null | To a suspension of 2-[(3-methyl-thiophen-2-ylmethyl)-amino]-thiazol-4-one (36.2. mg, 0.16 mmole), and 4-ethoxy-2-methylamino-quinazoline-6-carbaldehyde (example 12f, 45.5 mg, 0.20 mmole) in 2 mL of toluene in a microwave tube were added benzoic acid (2.0 mg, 0.016 mmole) and piperidine (1.5 mg, 0.02 mmole). The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1=NCCS1 | C1=NCCS1 | c1ccc2ncncc2c1.C1=NCCS1.c1ccsc1 | HO- | C1(=CC=CC=C1)C | 150 | null | CCOc1nc(NC)nc2ccc(C=O)cc12.Cc1ccsc1CNC1=NC(=O)CS1>C1(=CC=CC=C1)C>CCOc1nc(NC)nc2ccc(C=C3SC(NCc4sccc4C)=NC3=O)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-26ca6e323b3c47bda99c583f50a3b29a | NCc1ccc(F)c(Cl)c1.O=C1CSC(=S)N1>>O=C1CSC(NCc2ccc(F)c(Cl)c2)=N1 | CCN(C(C)C)C(C)C.ClC=1C=C(CN)C=CC1F.S1C(=S)NC(=O)C1>>ClC=1C=C(CNC=2SCC(N2)=O)C=CC1F | [NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([Cl:14])[cH:15]1.S=[C:5]1[S:4][CH2:3][C:2](=[O:1])[NH:16]1>>[O:1]=[C:2]1[CH2:3][S:4][C:5]([NH:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([F:12])[c:13]([Cl:14])[cH:15]2)=[N:16]1 | NCc1ccc(F)c(Cl)c1.O=C1CSC(=S)N1 | O=C1CSC(NCc2ccc(F)c(Cl)c2)=N1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 064ec4f4c9b054f21155524d05c8912d1c47d6f5ce3afcc6942dcefbbf4c33bd | 084147ade391ce0e1f4741b2f27289756f43b75fc8236974db260253a45beca1 | O=C1CSC(NCc2ccccc2)=N1 | S=[C;H0;D3;+0:1]1-[#16:2]-[C:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-1.[NH2;D1;+0:7]-[C:8]-[c:9]>>[O;D1;H0:5]=[C:4]1-[C:3]-[#16:2]-[C;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[c:9])=[N;H0;D2;+0:6]-1 | null | [] | null | null | null | null | Similar procedure as described in example 15a was used, starting with 3-chloro-4-fluoro-benzylamine, rhodanine, mercuric chloride and DIEA to give 2-(3-chloro-4-fluoro-benzylamino)-thiazol-4-one. LC-MS m/e 259 (MH+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Thioamide.Secondary amide.Primary amine | Secondary amine.Monosulfide | C1CSCN1 | C1=NCCS1 | C1=NCCS1.c1ccccc1 | Other | null | null | null | NCc1ccc(F)c(Cl)c1.O=C1CSC(=S)N1>>O=C1CSC(NCc2ccc(F)c(Cl)c2)=N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74f8334e53e642c69aef0092773c67d0 | NCc1ccc(F)cc1Cl.O=C1CSC(=S)N1>>O=C1CSC(NCc2ccc(F)cc2Cl)=N1 | CCN(C(C)C)C(C)C.ClC1=C(CN)C=CC(=C1)F.S1C(=S)NC(=O)C1>>ClC1=C(CNC=2SCC(N2)=O)C=CC(=C1)F | [NH2:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]1[Cl:15].S=[C:5]1[S:4][CH2:3][C:2](=[O:1])[NH:16]1>>[O:1]=[C:2]1[CH2:3][S:4][C:5]([NH:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[Cl:15])=[N:16]1 | NCc1ccc(F)cc1Cl.O=C1CSC(=S)N1 | O=C1CSC(NCc2ccc(F)cc2Cl)=N1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 064ec4f4c9b054f21155524d05c8912d1c47d6f5ce3afcc6942dcefbbf4c33bd | 084147ade391ce0e1f4741b2f27289756f43b75fc8236974db260253a45beca1 | O=C1CSC(NCc2ccccc2)=N1 | S=[C;H0;D3;+0:1]1-[#16:2]-[C:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-1.[NH2;D1;+0:7]-[C:8]-[c:9]>>[O;D1;H0:5]=[C:4]1-[C:3]-[#16:2]-[C;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[c:9])=[N;H0;D2;+0:6]-1 | null | [] | null | null | null | null | Similar procedure as described in example 15a was used, starting with 2-chloro-4-fluoro-benzylamine, rhodanine, mercuric chloride and DIEA to give 2-(2-chloro-4-fluoro-benzylamino)-thiazol-4-one. LC-MS m/e 259 (MH+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Thioamide.Secondary amide.Primary amine | Secondary amine.Monosulfide | C1CSCN1 | C1=NCCS1 | C1=NCCS1.c1ccccc1 | Other | null | null | null | NCc1ccc(F)cc1Cl.O=C1CSC(=S)N1>>O=C1CSC(NCc2ccc(F)cc2Cl)=N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b5bde04bde24eedbe620a834e25a596 | CCOc1nc(NC)nc2ccc(C=O)cc12.O=C1CSC(NCc2ccc(F)cc2Cl)=N1>>CCOc1nc(NC)nc2ccc(C=C3SC(NCc4ccc(F)cc4Cl)=NC3=O)cc12 | ClC1=C(CNC=2SCC(N2)=O)C=CC(=C1)F.C(C)OC1=NC(=NC2=CC=C(C=C12)C=O)NC.C(C1=CC=CC=C1)(=O)O.N1CCCCC1>>ClC1=C(CNC=2SC(C(N2)=O)=CC=2C=C3C(=NC(=NC3=CC2)NC)OCC)C=CC(=C1)F | O=[CH:14][c:13]1[cH:12][cH:11][c:10]2[n:9][c:6]([NH:7][CH3:8])[n:5][c:4]([O:3][CH2:2][CH3:1])[c:32]2[cH:31]1.[CH2:15]1[S:16][C:17]([NH:18][CH2:19][c:20]2[cH:21][cH:22][c:23]([F:24])[cH:25][c:26]2[Cl:27])=[N:28][C:29]1=[O:30]>>[CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]([NH:7][CH3:8])[n:9][c:10]2[cH:11][cH:12][c:13]([CH:14]=[C:... | CCOc1nc(NC)nc2ccc(C=O)cc12.O=C1CSC(NCc2ccc(F)cc2Cl)=N1 | CCOc1nc(NC)nc2ccc(C=C3SC(NCc4ccc(F)cc4Cl)=NC3=O)cc12 | null | null | C1(=CC=CC=C1)C | C-C Coupling | Aldol condensation | 269ab2e573a3c091a52ebc4e3efbf6cfa420243fb0cbe3e1b0cb45b4df823f3b | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1N=C(NCc2ccccc2)SC1=Cc1ccc2ncncc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]=[C:8]-[#16:9]-[CH2;D2;+0:10]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]=[C:8]-[#16:9]-[C;H0;D3;+0:10]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 150 | CELSIUS | null | null | To a suspension of 2-(2-chloro-4-fluoro-benzylamino)-thiazol-4-one (example 17a, 41.4 mg, 0.16 mmole), and 4-ethoxy-2-methylamino-quinazoline-6-carbaldehyde (example 12f, 45.5 mg, 0.20 mmole) in 2 mL of toluene in a microwave tube were added benzoic acid (2.0 mg, 0.016 mmole) and piperidine (1.5 mg, 0.02 mmole). The re... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1=NCCS1 | C1=NCCS1 | c1ccc2ncncc2c1.C1=NCCS1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | 150 | null | CCOc1nc(NC)nc2ccc(C=O)cc12.O=C1CSC(NCc2ccc(F)cc2Cl)=N1>C1(=CC=CC=C1)C>CCOc1nc(NC)nc2ccc(C=C3SC(NCc4ccc(F)cc4Cl)=NC3=O)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef29e45a96734e8fa693f15b781c59b7 | Cc1cccc(Cl)c1CN.O=C1CSC(=S)N1>>Cc1cccc(Cl)c1CNC1=NC(=O)CS1 | CCN(C(C)C)C(C)C.ClC1=C(CN)C(=CC=C1)C.S1C(=S)NC(=O)C1>>ClC1=C(CNC=2SCC(N2)=O)C(=CC=C1)C | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([Cl:7])[c:8]1[CH2:9][NH2:10].S=[C:11]1[NH:12][C:13](=[O:14])[CH2:15][S:16]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([Cl:7])[c:8]1[CH2:9][NH:10][C:11]1=[N:12][C:13](=[O:14])[CH2:15][S:16]1 | Cc1cccc(Cl)c1CN.O=C1CSC(=S)N1 | Cc1cccc(Cl)c1CNC1=NC(=O)CS1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 064ec4f4c9b054f21155524d05c8912d1c47d6f5ce3afcc6942dcefbbf4c33bd | 084147ade391ce0e1f4741b2f27289756f43b75fc8236974db260253a45beca1 | O=C1CSC(NCc2ccccc2)=N1 | S=[C;H0;D3;+0:1]1-[#16:2]-[C:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-1.[NH2;D1;+0:7]-[C:8]-[c:9]>>[O;D1;H0:5]=[C:4]1-[C:3]-[#16:2]-[C;H0;D3;+0:1](-[NH;D2;+0:7]-[C:8]-[c:9])=[N;H0;D2;+0:6]-1 | null | [] | null | null | null | null | Similar procedure as described in example 15a was used, starting with 2-chloro-6-methyl-benzylamine, rhodanine, mercuric chloride and DIEA to give 2-(2-chloro-6-methyl-benzylamino)-thiazol-4-one. LC-MS m/e 259 (MH+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Thioamide.Secondary amide.Primary amine | Secondary amine.Monosulfide | C1CSCN1 | C1=NCCS1 | c1ccccc1.C1=NCCS1 | Other | null | null | null | Cc1cccc(Cl)c1CN.O=C1CSC(=S)N1>>Cc1cccc(Cl)c1CNC1=NC(=O)CS1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-49a9ffcf884e421da94d258bd01174a3 | CCOc1nc(NC)nc2ccc(C=O)cc12.Cc1cccc(Cl)c1CNC1=NC(=O)CS1>>CCOc1nc(NC)nc2ccc(C=C3SC(NCc4c(C)cccc4Cl)=NC3=O)cc12 | ClC1=C(CNC=2SCC(N2)=O)C(=CC=C1)C.C(C)OC1=NC(=NC2=CC=C(C=C12)C=O)NC.C(C1=CC=CC=C1)(=O)O.N1CCCCC1>>ClC1=C(CNC=2SC(C(N2)=O)=CC=2C=C3C(=NC(=NC3=CC2)NC)OCC)C(=CC=C1)C | O=[CH:14][c:13]1[cH:12][cH:11][c:10]2[n:9][c:6]([NH:7][CH3:8])[n:5][c:4]([O:3][CH2:2][CH3:1])[c:32]2[cH:31]1.[CH2:15]1[S:16][C:17]([NH:18][CH2:19][c:20]2[c:21]([CH3:22])[cH:23][cH:24][cH:25][c:26]2[Cl:27])=[N:28][C:29]1=[O:30]>>[CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]([NH:7][CH3:8])[n:9][c:10]2[cH:11][cH:12][c:13]([CH:14]=[... | CCOc1nc(NC)nc2ccc(C=O)cc12.Cc1cccc(Cl)c1CNC1=NC(=O)CS1 | CCOc1nc(NC)nc2ccc(C=C3SC(NCc4c(C)cccc4Cl)=NC3=O)cc12 | null | null | C1(=CC=CC=C1)C | C-C Coupling | Aldol condensation | 269ab2e573a3c091a52ebc4e3efbf6cfa420243fb0cbe3e1b0cb45b4df823f3b | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1N=C(NCc2ccccc2)SC1=Cc1ccc2ncncc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]=[C:8]-[#16:9]-[CH2;D2;+0:10]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]=[C:8]-[#16:9]-[C;H0;D3;+0:10]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 150 | CELSIUS | null | null | To a suspension of 2-(2-chloro-6-methyl-benzylamino)-thiazol-4-one (example 18a, 40.8 mg, 0.16 mmole), and 4-ethoxy-2-methylamino-quinazoline-6-carbaldehyde (example 12f, 45.5 mg, 0.20 mmole) in 2 mL of toluene in a microwave tube were added benzoic acid (2.0 mg, 0.016 mmole) and piperidine (1.5 mg, 0.02 mmole). The re... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1=NCCS1 | C1=NCCS1 | c1ccc2ncncc2c1.C1=NCCS1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | 150 | null | CCOc1nc(NC)nc2ccc(C=O)cc12.Cc1cccc(Cl)c1CNC1=NC(=O)CS1>C1(=CC=CC=C1)C>CCOc1nc(NC)nc2ccc(C=C3SC(NCc4c(C)cccc4Cl)=NC3=O)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-46c5bfcfed364968b925e922f4a2064c | NCc1cccs1.O=C1CSC(=S)N1>>O=C1CSC(NCc2cccs2)=N1 | CCN(C(C)C)C(C)C.S1C(=CC=C1)CN.S1C(=S)NC(=O)C1>>S1C(=CC=C1)CNC=1SCC(N1)=O | [NH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][s:12]1.S=[C:5]1[S:4][CH2:3][C:2](=[O:1])[NH:13]1>>[O:1]=[C:2]1[CH2:3][S:4][C:5]([NH:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][s:12]2)=[N:13]1 | NCc1cccs1.O=C1CSC(=S)N1 | O=C1CSC(NCc2cccs2)=N1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 064ec4f4c9b054f21155524d05c8912d1c47d6f5ce3afcc6942dcefbbf4c33bd | 084147ade391ce0e1f4741b2f27289756f43b75fc8236974db260253a45beca1 | O=C1CSC(NCc2cccs2)=N1 | S=[C;H0;D3;+0:1]1-[#16:2]-[C:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-1.[#16;a:7]:[c:8]-[C:9]-[NH2;D1;+0:10]>>[#16;a:7]:[c:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1]1=[N;H0;D2;+0:6]-[C:4](=[O;D1;H0:5])-[C:3]-[#16:2]-1 | null | [] | null | null | null | null | Similar procedure as described in example 15a was used, starting with thiophen-2-ylmethyl-amine, rhodanine, mercuric chloride and DIEA to give 2-(thiophen-2-ylmethyl-amino)-thiazol-4-one. LC-MS m/e 259 (MH+).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Thioamide.Secondary amide.Primary amine | Secondary amine.Monosulfide | C1CSCN1 | C1=NCCS1 | C1=NCCS1.c1ccsc1 | Other | null | null | null | NCc1cccs1.O=C1CSC(=S)N1>>O=C1CSC(NCc2cccs2)=N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-49f3bc5cad5e43df963509fa7841c881 | CCOc1nc(NC)nc2ccc(C=O)cc12.O=C1CSC(NCc2cccs2)=N1>>CCOc1nc(NC)nc2ccc(C=C3SC(NCc4cccs4)=NC3=O)cc12 | S1C(=CC=C1)CNC=1SCC(N1)=O.C(C)OC1=NC(=NC2=CC=C(C=C12)C=O)NC.C(C1=CC=CC=C1)(=O)O.N1CCCCC1>>C(C)OC1=NC(=NC2=CC=C(C=C12)C=C1C(N=C(S1)NCC=1SC=CC1)=O)NC | O=[CH:14][c:13]1[cH:12][cH:11][c:10]2[n:9][c:6]([NH:7][CH3:8])[n:5][c:4]([O:3][CH2:2][CH3:1])[c:29]2[cH:28]1.[CH2:15]1[S:16][C:17]([NH:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][s:24]2)=[N:25][C:26]1=[O:27]>>[CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]([NH:7][CH3:8])[n:9][c:10]2[cH:11][cH:12][c:13]([CH:14]=[C:15]3[S:16][C:17]([NH:... | CCOc1nc(NC)nc2ccc(C=O)cc12.O=C1CSC(NCc2cccs2)=N1 | CCOc1nc(NC)nc2ccc(C=C3SC(NCc4cccs4)=NC3=O)cc12 | null | null | C1(=CC=CC=C1)C | C-C Coupling | Aldol condensation | 269ab2e573a3c091a52ebc4e3efbf6cfa420243fb0cbe3e1b0cb45b4df823f3b | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1N=C(NCc2cccs2)SC1=Cc1ccc2ncncc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]=[C:8]-[#16:9]-[CH2;D2;+0:10]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]=[C:8]-[#16:9]-[C;H0;D3;+0:10]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 150 | CELSIUS | null | null | To a suspension of 2-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one (34.0 mg, 0.16 mmole), and 4-ethoxy-2-methylamino-quinazoline-6-carbaldehyde (example 12f, 45.5 mg, 0.20 mmole) in 2 mL of toluene in a microwave tube were added benzoic acid (2.0 mg, 0.016 mmole) and piperidine (1.5 mg, 0.02 mmole). The reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1=NCCS1 | C1=NCCS1 | c1ccc2ncncc2c1.C1=NCCS1.c1ccsc1 | HO- | C1(=CC=CC=C1)C | 150 | null | CCOc1nc(NC)nc2ccc(C=O)cc12.O=C1CSC(NCc2cccs2)=N1>C1(=CC=CC=C1)C>CCOc1nc(NC)nc2ccc(C=C3SC(NCc4cccs4)=NC3=O)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-46aecee3d5644a9582b7730083cfa691 | CCOc1nc(NC)nc2ccc(C=O)cc12.O=C1CSC(NCCc2cccc(F)c2)=N1>>CCOc1nc(NC)nc2ccc(C=C3SC(NCCc4cccc(F)c4)=NC3=O)cc12 | FC=1C=C(C=CC1)CCNC=1SCC(N1)=O.C(C)OC1=NC(=NC2=CC=C(C=C12)C=O)NC.C(C1=CC=CC=C1)(=O)O.N1CCCCC1>>C(C)OC1=NC(=NC2=CC=C(C=C12)C=C1C(N=C(S1)NCCC1=CC(=CC=C1)F)=O)NC | O=[CH:14][c:13]1[cH:12][cH:11][c:10]2[n:9][c:6]([NH:7][CH3:8])[n:5][c:4]([O:3][CH2:2][CH3:1])[c:32]2[cH:31]1.[CH2:15]1[S:16][C:17]([NH:18][CH2:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][c:25]([F:26])[cH:27]2)=[N:28][C:29]1=[O:30]>>[CH3:1][CH2:2][O:3][c:4]1[n:5][c:6]([NH:7][CH3:8])[n:9][c:10]2[cH:11][cH:12][c:13]([CH:14]=[... | CCOc1nc(NC)nc2ccc(C=O)cc12.O=C1CSC(NCCc2cccc(F)c2)=N1 | CCOc1nc(NC)nc2ccc(C=C3SC(NCCc4cccc(F)c4)=NC3=O)cc12 | null | null | C1(=CC=CC=C1)C | C-C Coupling | Aldol condensation | 269ab2e573a3c091a52ebc4e3efbf6cfa420243fb0cbe3e1b0cb45b4df823f3b | d1104e4dc387c28c5ac408eab23aa043e968d3cfd16e99022454bf87ce31f401 | O=C1N=C(NCCc2ccccc2)SC1=Cc1ccc2ncncc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6]1-[#7:7]=[C:8]-[#16:9]-[CH2;D2;+0:10]-1>>[O;D1;H0:5]=[C:6]1-[#7:7]=[C:8]-[#16:9]-[C;H0;D3;+0:10]-1=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 150 | CELSIUS | null | null | To a suspension of 2-[2-(3-fluoro-phenyl)-ethylamino]-thiazol-4-one (example 10c, 38.1 mg, 0.16 mmole), and 4-ethoxy-2-methylamino-quinazoline-6-carbaldehyde (example 12f, 45.5 mg, 0.20 mmole) in 2 mL of toluene in a microwave tube were added benzoic acid (2.0 mg, 0.016 mmole) and piperidine (1.5 mg, 0.02 mmole). The r... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Monosulfide | Monosulfide | C1=NCCS1 | C1=NCCS1 | c1ccc2ncncc2c1.C1=NCCS1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | 150 | null | CCOc1nc(NC)nc2ccc(C=O)cc12.O=C1CSC(NCCc2cccc(F)c2)=N1>C1(=CC=CC=C1)C>CCOc1nc(NC)nc2ccc(C=C3SC(NCCc4cccc(F)c4)=NC3=O)cc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-66a02b1f01c7404e9caa322feff8cdd1 | BrCc1cccnc1.COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)NCC3>>COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(Cc1cccnc1)CC3 | Cl.COC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3.C(C)N(CC)CC.Br.BrCC=1C=NC=CC1.Br>>Br.COC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3CC=3C=NC=CC3 | Br[CH2:19][c:20]1[cH:21][cH:22][cH:23][n:24][cH:25]1.[CH3:2][O:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C@@:10]13[CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]1[C@@H:16]([CH2:17]2)[NH:18][CH2:26][CH2:27]3>>[CH3:2][O:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C@@:10]13[CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]1[C@@H:16]([CH2:17]2... | BrCc1cccnc1.COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)NCC3 | COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(Cc1cccnc1)CC3 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | d6e7f6e98779c888d504f2d324d290f2169204ce293e83f8a98f533bb30938c4 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cncc(CN2CC[C@]34CCCC[C@H]3[C@H]2Cc2ccccc24)c1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[C:7]-[C:8](-[C:9])-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:7]-[C:8](-[C:9])-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6])-[C:11]-[C:12] | 68 | [{"value": 68.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Similarly to the preparation of Example 4, the title compound was prepared from the reaction of (+)-3-methoxy-morphinan hydrochloride (1 g, 3.4 mmol) in THF (20 ml), triethylamine (1.43 ml, 10.3 mmol), and 3-(bromomethyl)pyridine hydrobromide (0.95 g, 3.75 mmol) gave a solid which was treated with 45% HBr to afford 1 g... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1ccc2c(c1)C[C@H]1NCC[C@@]23CCCC[C@@H]13 | c1ccc2c(c1)C[C@H]1[NH]CC[C@@]23CCCC[C@@H]13 | c1ccncc1.c1ccc2c(c1)C[C@H]1[NH]CC[C@@]23CCCC[C@@H]13 | HBr | C1CCOC1 | null | null | BrCc1cccnc1.COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)NCC3>C1CCOC1>COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(Cc1cccnc1)CC3 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb375a2a499941a982c6603454deb9e9 | CS(=O)(=O)Cl.OCc1cccs1>>CS(=O)(=O)OCc1cccs1 | S1C(=CC=C1)CO.C(C)N(CC)CC.CS(=O)(=O)Cl>>S(C)(=O)(=O)OCC=1SC=CC1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][s:11]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][c:7]1[cH:8][cH:9][cH:10][s:11]1 | CS(=O)(=O)Cl.OCc1cccs1 | CS(=O)(=O)OCc1cccs1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccsc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#16;a:5]:[c:6]-[C:7]-[OH;D1;+0:8]>>[#16;a:5]:[c:6]-[C:7]-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | null | null | 2-thienylmethanol mesylate is prepared by treating a solution of 2-thienylmethanol (5.57 g; 50 mmol) in methylene chloride (100 ml) and triethylamine (15.05 g, 150 mmol) at 0° C. with methanesulfonyl chloride (11.45 g, 100 mmol) dropwise and at RT 1 hr after the addition. The reaction mixture is poured into ice-water a... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccsc1 | HCl | C(Cl)Cl | null | null | CS(=O)(=O)Cl.OCc1cccs1>C(Cl)Cl>CS(=O)(=O)OCc1cccs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d7d00c2b9cdc4c18aaa938fb269d474e | CC(=O)OC(C)=O.COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)NCC3>>COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(C(C)=O)CC3 | C(C)(=O)OC(C)=O.Cl.COC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3.C(C)N(CC)CC>>COC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3C(C)=O | CC(=O)O[C:18]([CH3:19])=[O:20].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C@@:9]13[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]1[C@@H:15]([CH2:16]2)[NH:17][CH2:21][CH2:22]3>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C@@:9]13[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]1[C@@H:15]([CH2:16]2)[N:17]([C:18]([CH3:19])... | CC(=O)OC(C)=O.COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)NCC3 | COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(C(C)=O)CC3 | null | null | C1CCOC1 | Acylation | Aminolysis of esters | 624b7fc38699106de131f7576aa29ac24877d55b705371bb810ca254b65f8ffd | 6593c6062585994f02076cd3c86920ae7244b86659eab65c21b5a8628c6d4bb8 | c1ccc2c(c1)C[C@H]1NCC[C@@]23CCCC[C@@H]13 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[C:6])-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:4]-[C:5](-[C:6])-[N;H0;D3;+0:7](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:8]-[C:9] | 81.9 | [{"value": 81.0, "product": "COC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.9, "product": "COC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | Acetic anhydride (3.14 g, 30.76 mmol) was added to a solution of (+)-3-methoxy-morphinan hydrochloride (1.5 g, 5.1 mmol) in THF (30 ml) and triethylamine (8.7 g, 85.98 mmol) in the presence of nitrogen. The resulting solution was heated at 60° C. for 15 hr. The reaction mixture was cooled to room temperature and evapor... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amine | Tertiary amide | c1ccc2c(c1)C[C@H]1NCC[C@@]23CCCC[C@@H]13 | c1ccc2c(c1)C[C@H]1[NH]CC[C@@]23CCCC[C@@H]13 | c1ccc2c(c1)C[C@H]1[NH]CC[C@@]23CCCC[C@@H]13 | HO- | C1CCOC1 | 60 | null | CC(=O)OC(C)=O.COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)NCC3>C1CCOC1>COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(C(C)=O)CC3 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6d7d1b76c64b4f4bb2e305aa3f7ffb72 | COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)NCC3.O=C(O)c1ccc2[nH]ccc2c1>>COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(C(=O)c1ccc2[nH]ccc2c1)CC3 | C(C)N(CC)CC.C(C(=O)Cl)(=O)Cl.N1C=CC2=CC(=CC=C12)C(=O)O.Cl.COC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3>>COC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3C(=O)C=3C=C1C=CNC1=CC3 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C@@:9]13[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]1[C@@H:15]([CH2:16]2)[NH:17][CH2:29][CH2:30]3.O[C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]2[nH:24][cH:25][cH:26][c:27]2[cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C@@:9]13[CH2:10][CH2:11][CH2:12][CH2:13][C... | COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)NCC3.O=C(O)c1ccc2[nH]ccc2c1 | COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(C(=O)c1ccc2[nH]ccc2c1)CC3 | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 6ec84e357728f8c8343283fad132830039b758c15c96855f9a1bc8bb56f35291 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccc2[nH]ccc2c1)N1CC[C@]23CCCC[C@H]2[C@H]1Cc1ccccc13 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[C:8])-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:6]-[C:7](-[C:8])-[N;H0;D3;+0:9](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:10]-[C:11] | 28 | [{"value": 28.0, "product": "COC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3C(=O)C=3C=C1C=CNC1=CC3", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.0, "product": "COC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3C(=O)C=3C=C1C=CNC1=CC3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | Oxalyl chloride (15 ul, 0.14 mmol) at RT was added to a solution of indole-5-carboxylic acid (0.02 g, 0.12 mmol) in THF (1 ml). After stirring at RT for 10 h, the mixture was added THF (1 ml) followed by (+)-3-methoxy-morphinan hydrochloride (0.04 g, 0.12 mmol), then triethylamine (0.1 ml, 0.7 mmol) was added and stirr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | c1ccc2c(c1)C[C@H]1NCC[C@@]23CCCC[C@@H]13 | c1ccc2c(c1)C[C@H]1[NH]CC[C@@]23CCCC[C@@H]13 | c1ccc2[nH]ccc2c1.c1ccc2c(c1)C[C@H]1[NH]CC[C@@]23CCCC[C@@H]13 | HO- | C1CCOC1 | null | 10 | COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)NCC3.O=C(O)c1ccc2[nH]ccc2c1>C1CCOC1>COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(C(=O)c1ccc2[nH]ccc2c1)CC3 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6715e9f681ca4ab4baa95357fa832779 | Cc1ccc(CC2C3=C(CCCC3)CCN2C)cc1>>Cc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(C)CC3 | N.CC1=CC=C(CC2N(CCC=3CCCCC23)C)C=C1.P(O)(O)(O)=O>>CC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:15][CH:14]2[C:13]3=[C:8]([CH2:9][CH2:10][CH2:11][CH2:12]3)[CH2:19][CH2:18][N:16]2[CH3:17])[cH:6][cH:7]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C@@:8]13[CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]1[C@@H:14]([CH2:15]2)[N:16]([CH3:17])[CH2:18][CH2:19]3 | Cc1ccc(CC2C3=C(CCCC3)CCN2C)cc1 | Cc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(C)CC3 | null | null | O | C-C Coupling | OtherReaction | 844ea2338c23c51e2632ce16be5deb073b2d6bf2c7af5dedf5580d59c9b42547 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | c1ccc2c(c1)C[C@H]1NCC[C@@]23CCCC[C@@H]13 | [C;D1;H3:1]-[#7:2]1-[C:3]-[C:4]-[C;H0;D3;+0:5]2=[C;H0;D3;+0:6](-[C:7]-[C:8]-[C:9]-[C:10]-2)-[CH;D3;+0:11]-1-[C:12]-[c:13](:[c:14]):[cH;D2;+0:15]:[c:16]:[c:17]>>[C;D1;H3:1]-[#7:2]1-[C:3]-[C:4]-[C@;H0;D4;+0:5]23-[C:10]-[C:9]-[C:8]-[C:7]-[C@H;D3;+0:6]-2-[C@H;D3;+0:11]-1-[C:12]-[c:13](:[c:14]):[c;H0;D3;+0:15]-3:[c:16]:[c:1... | 27.5 | [{"value": 27.5, "product": "CC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 135 | CELSIUS | null | null | (+)-1-p-methylbenzyl-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline (26.5 g) was added to 85% phosphoric acid (130 ml) and the mixture was heated to 130-140° C. for 72 h. After the reaction was complete, the reaction mixture was poured into ice-water and the solution was made strongly alkaline by the addition of conc. ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1.C1CCC2=C(C1)CC[NH]C2 | c1ccc2c(c1)C[C@H]1[NH]CC[C@@]23CCCC[C@@H]13 | c1ccc2c(c1)C[C@H]1[NH]CC[C@@]23CCCC[C@@H]13 | null | O | 135 | null | Cc1ccc(CC2C3=C(CCCC3)CCN2C)cc1>O>Cc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(C)CC3 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-82721697c26e4583bd5e8d3a8bccfbe3 | COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)NCC3.O=[N+]([O-])c1ccc(Br)cc1>>COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(c1ccc([N+](=O)[O-])cc1)CC3 | P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.CCCCCC.O([Na])C(C)(C)C.COC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3.[N+](=O)([O-])C1=CC=C(C=C1)Br>>COC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3C3=CC=C(C=C3)[N+](=O)[O-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C@@:9]13[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]1[C@@H:15]([CH2:16]2)[NH:17][CH2:27][CH2:28]3.Br[c:18]1[cH:19][cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25][cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C@@:9]13[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]1[C@@... | COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)NCC3.O=[N+]([O-])c1ccc(Br)cc1 | COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(c1ccc([N+](=O)[O-])cc1)CC3 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | C1(=CC=CC=C1)C.C(Cl)Cl | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 4fcec184e9ed8a4453123071428c066e35723349125d7e939a62d47c304f0608 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CC[C@]34CCCC[C@H]3[C@H]2Cc2ccccc24)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7](-[C:8])-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:6]-[C:7](-[C:8])-[N;H0;D3;+0:9](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:10]-[C:11] | 30 | [{"value": 30.0, "product": "COC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3C3=CC=C(C=C3)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | Pd(OAc)2 (1.34 mg, 0.006 mmol) and 10% solution of P(t-Bu)3 in hexane (0.015 ml, 0.0048 mmol) were added to the suspension of NaO-t-Bu (86.4 g, 0.9 mmol), (+)-3-methoxy-morphinan (0.1645 g, 0.5 mmol) and 4-(nitro)-bromobenzene (0.1212 g, 0.6 mmol) in toluene (˜12 mL) in the presence of nitrogen. The resulting mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2c(c1)C[C@H]1NCC[C@@]23CCCC[C@@H]13.c1ccccc1 | c1ccccc1.c1ccc2c(c1)C[C@H]1[NH]CC[C@@]23CCCC[C@@H]13 | c1ccccc1.c1ccc2c(c1)C[C@H]1[NH]CC[C@@]23CCCC[C@@H]13 | HBr | CC(=O)[O-].CC(=O)[O-].[Pd+2].C1(=CC=CC=C1)C.C(Cl)Cl | 80 | null | COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)NCC3.O=[N+]([O-])c1ccc(Br)cc1>CC(=O)[O-].CC(=O)[O-].[Pd+2].C1(=CC=CC=C1)C.C(Cl)Cl>COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(c1ccc([N+](=O)[O-])cc1)CC3 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4df8c80e64824293bdb3f968211548c3 | COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(c1ccc([N+](=O)[O-])cc1)CC3>>COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(c1ccccc1)CC3 | P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.CCCCCC.O([Na])C(C)(C)C.COC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3C3=CC=C(C=C3)[N+](=O)[O-]>>COC=1C=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C2C1)CCN3C3=CC=CC=C3 | O=[N+]([O-])[c:21]1[cH:20][cH:19][c:18]([N:17]2[C@H:15]3[C@H:14]4[C@@:9]([c:7]5[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]5)[CH2:16]3)([CH2:10][CH2:11][CH2:12][CH2:13]4)[CH2:25][CH2:24]2)[cH:23][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C@@:9]13[CH2:10][CH2:11][CH2:12][CH2:13][C@H:14]1[C@@H:15]([CH2:1... | COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(c1ccc([N+](=O)[O-])cc1)CC3 | COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(c1ccccc1)CC3 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | null | Reduction | OtherReaction | 525eee524a7f66e15606f7834cdf83cedc15bc71d11833eaff42c5ce617a109c | a48304f1d491232fd73e82261ecea998a2c4787d8fac4a6a0f69a35adfcacd2c | c1ccc(N2CC[C@]34CCCC[C@H]3[C@H]2Cc2ccccc24)cc1 | O=[N+](-[O-])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[c:3]:[c:2]:[cH;D2;+0:1]:[c:4]:[c:5] | null | [] | null | null | null | null | Similar to the preparation of the compound of Example 13, the title compound is made from the reaction of Pd(OAc)2 (1.34 mg, 0.006 mmol), 10% solution of P(t-Bu)3 in hexane (0.015 ml, 0.0048 mmol), and NaO-t-Bu (86.4 g, 0.9 mmol) in the presence of argon and then a solution of (+)-3-methoxy-morphinan (0.1645 g, 0.5 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)C[C@H]1[NH]CC[C@@]23CCCC[C@@H]13 | Other | CC(=O)[O-].CC(=O)[O-].[Pd+2] | null | null | COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(c1ccc([N+](=O)[O-])cc1)CC3>CC(=O)[O-].CC(=O)[O-].[Pd+2]>COc1ccc2c(c1)[C@@]13CCCC[C@H]1[C@@H](C2)N(c1ccccc1)CC3 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-15d10bd3f6654c2abf1d809adcfc24c0 | BrCc1ccccc1.O=c1[nH]nc(Br)c2ccccc12>>O=c1c2ccccc2c(Br)nn1Cc1ccccc1 | C(C1=CC=CC=C1)Br.BrC1=NNC(C2=CC=CC=C12)=O.[H-].[Na+]>>C(C1=CC=CC=C1)N1C(C2=CC=CC=C2C(=N1)Br)=O | Br[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[O:1]=[c:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[c:9]([Br:10])[n:11][nH:12]1>>[O:1]=[c:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[c:9]([Br:10])[n:11][n:12]1[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | BrCc1ccccc1.O=c1[nH]nc(Br)c2ccccc12 | O=c1c2ccccc2c(Br)nn1Cc1ccccc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6baf9aa5a5bdd72a5bd77d59c3dada954aa9fe8ebd1adaa11fdfc80a754826ab | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1c2ccccc2cnn1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[c:6](:[c:7]):[nH;D2;+0:8]:[#7;a:9]:[c:10]>>[O;D1;H0:5]=[c:6](:[c:7]):[n;H0;D3;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[#7;a:9]:[c:10] | 56.3 | [{"value": 56.0, "product": "C(C1=CC=CC=C1)N1C(C2=CC=CC=C2C(=N1)Br)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.3, "product": "C(C1=CC=CC=C1)N1C(C2=CC=CC=C2C(=N1)Br)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 4-Bromo-2H-phthalazin-1-one (10.38 g, 46 mmol) was dissolved in dimethylformamide (DMF) (60 ml). To this was added NaH (60%, 1.55 g, 46.2 mmol) as a DMF suspension (20 ml). The mixture was stirred at RT for 30 mins then benzyl bromide (13.82 g, 50.8 mmol) was added in one portion as a solution in DMF (20 ml). The react... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1nncc2ccccc12 | c1ccc2cnncc2c1 | c1ccc2cnncc2c1.c1ccccc1 | HBr | CN(C=O)C | null | 0.5 | BrCc1ccccc1.O=c1[nH]nc(Br)c2ccccc12>CN(C=O)C>O=c1c2ccccc2c(Br)nn1Cc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c6f143917e1e44e6a87f700fe28f140d | Cc1cc(Nc2nn(CC(=O)c3ccccc3)c(=O)c3ccccc23)n[nH]1>>Cc1cc(Nc2nn(CC(O)c3ccccc3)c(=O)c3ccccc23)n[nH]1 | [BH4-].[Na+].CC1=CC(=NN1)NC1=NN(C(C2=CC=CC=C12)=O)CC(C1=CC=CC=C1)=O>>OC(CN1C(C2=CC=CC=C2C(=N1)NC1=NNC(=C1)C)=O)C1=CC=CC=C1 | [CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8]([CH2:9][C:10](=[O:11])[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:18](=[O:19])[c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]23)[n:26][nH:27]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8]([CH2:9][CH:10]([OH:11])[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[c:18](=[O:19])[... | Cc1cc(Nc2nn(CC(=O)c3ccccc3)c(=O)c3ccccc23)n[nH]1 | Cc1cc(Nc2nn(CC(O)c3ccccc3)c(=O)c3ccccc23)n[nH]1 | null | null | C1CCOC1 | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | O=c1c2ccccc2c(Nc2cc[nH]n2)nn1CCc1ccccc1 | [#7;a:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[#7;a:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7] | 12.2 | [{"value": 12.0, "product": "OC(CN1C(C2=CC=CC=C2C(=N1)NC1=NNC(=C1)C)=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.2, "product": "OC(CN1C(C2=CC=CC=C2C(=N1)NC1=NNC(=C1)C)=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Sodium borohydride (6 mg, 0.15 mmol) was added in one portion to a stirred solution of 4-(5-Methyl-1H-pyrazol-3-ylamino)-2-(2-oxo-2-phenyl-ethyl)-2H-phthalazin-1-one (17 mg, 0.05 mmol) (Example E-9) in THF (1 ml). The reaction mixture was stirred at RT for two hours. After this time LC-MS indicated complete consumption... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1cn[nH]c1.c1ccccc1.c1ccc2cnncc2c1 | null | C1CCOC1 | null | 2 | Cc1cc(Nc2nn(CC(=O)c3ccccc3)c(=O)c3ccccc23)n[nH]1>C1CCOC1>Cc1cc(Nc2nn(CC(O)c3ccccc3)c(=O)c3ccccc23)n[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bc96dc780e294cfc97da8f03327e0fdb | CC(Br)CO.O=c1[nH]nc(Br)c2ccc([N+](=O)[O-])cc12>>CC(C)n1nc(Br)c2ccc([N+](=O)[O-])cc2c1=O | [H-].[Na+].[H-].[Na+].BrC(CO)C.[N+](=O)([O-])C1=CC=C2C(=NNC(C2=C1)=O)Br>>[N+](=O)([O-])C1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br | O[CH2:3][CH:2](Br)[CH3:1].[nH:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]2[c:17]1=[O:18]>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]2[c:17]1=[O:18] | CC(Br)CO.O=c1[nH]nc(Br)c2ccc([N+](=O)[O-])cc12 | CC(C)n1nc(Br)c2ccc([N+](=O)[O-])cc2c1=O | null | null | CN(C=O)C | Functional Group Addition | OtherReaction | f75b244bf38a1cd663e2e5ba43469af9c7d04578ab5fad147069f6a5c1607a49 | 9e032178aca13feb73035ffbdf1bb99b66e7236d3e4262ac6530df8f2873c555 | O=c1[nH]ncc2ccccc12 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-O.[O;D1;H0:4]=[c:5](:[c:6]):[nH;D2;+0:7]:[#7;a:8]:[c:9]>>[C;D1;H3:2]-[CH;D3;+0:1](-[CH3;D1;+0:3])-[n;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:5](=[O;D1;H0:4]):[c:6] | 200.5 | [{"value": 40.0, "product": "[N+](=O)([O-])C1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 200.5, "product": "[N+](=O)([O-])C1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 7-Nitro-4-bromo-2H-phthalazin-1-one (84 g, 0.31 mol) was dissolved in dimethylformamide (DMF) (400 ml). To this was added NaH (60%, 7.5 g, 0.31 mol) as a DMF suspension (200 ml). The mixture was stirred at RT for 30 min then 2-bromo-propanol (7.7 g, 62 mmol) was added in one portion as a solution in DMF (250 ml). The r... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary alcohol | null | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | HBr | CN(C=O)C | null | 0.5 | CC(Br)CO.O=c1[nH]nc(Br)c2ccc([N+](=O)[O-])cc12>CN(C=O)C>CC(C)n1nc(Br)c2ccc([N+](=O)[O-])cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-00e3a981a4f744c4b8c8a283b4d93bc2 | CC(C)n1nc(Br)c2ccc([N+](=O)[O-])cc2c1=O>>CC(C)n1nc(Br)c2ccc(N)cc2c1=O | [N+](=O)([O-])C1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br.Cl>>NC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[c:6]([Br:7])[n:5][n:4]([CH:2]([CH3:1])[CH3:3])[c:15](=[O:16])[c:14]2[cH:13]1>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:13][c:14]2[c:15]1=[O:16] | CC(C)n1nc(Br)c2ccc([N+](=O)[O-])cc2c1=O | CC(C)n1nc(Br)c2ccc(N)cc2c1=O | null | [Fe] | O.CCO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1[nH]ncc2ccccc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99.2 | [{"value": 98.0, "product": "NC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.2, "product": "NC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 7-Nitro-2-Isopropyl-4-bromo-2H-phthalazin-1-one (4.6 g, 0.015 mol) was dissolved in a 5:1 mixture of EtOH and water (150 ml). To this solution was added iron powder (2.14 g, 0.039 mol) and concentrated HCl (1 ml), the mixture was heated to 80° C. for three hours. After this time, the reaction mixture was cooled to RT a... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2cnncc2c1 | Other | [Fe].O.CCO | 80 | null | CC(C)n1nc(Br)c2ccc([N+](=O)[O-])cc2c1=O>[Fe].O.CCO>CC(C)n1nc(Br)c2ccc(N)cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-44cb8c55a5864b4ba8165ac3f64e8624 | CC(C)n1nc(Br)c2ccc(N)cc2c1=O.ClCCOCCCl>>CC(C)n1nc(Br)c2ccc(N3CCOCC3)cc2c1=O | ClCCOCCCl.NC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br.C([O-])([O-])=O.[K+].[K+]>>O1CCN(CC1)C1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br | [CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:18][c:19]2[c:20]1=[O:21].Cl[CH2:13][CH2:14][O:15][CH2:16][CH2:17]Cl>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([N:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)[cH:18][c:19]2[c:20]1=[O:21] | CC(C)n1nc(Br)c2ccc(N)cc2c1=O.ClCCOCCCl | CC(C)n1nc(Br)c2ccc(N3CCOCC3)cc2c1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 96e983e5a21a49df63baecef913e7d3b8dacd6365c270725738379ba775c02bb | 631870b1ab33be0edc94bc9ae10321f1c5ede4dd4db77035c9d3979e4a2118fb | O=c1[nH]ncc2ccc(N3CCOCC3)cc12 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-Cl.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[N;H0;D3;+0:6]1-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-1):[c:9] | 20.3 | [{"value": 20.0, "product": "O1CCN(CC1)C1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.3, "product": "O1CCN(CC1)C1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 5 | MINUTE | To a solution of 7-Amino-2-Isopropyl-4-bromo-2H-phthalazin-1-one (0.8 g, 0.0028 mol) in DMF (8 ml), was added potassium carbonate (2 g, 0.014 mol). After 5 min, bis (2-chloroethyl) ether (0.41 g, 0.0028 mol) was added and the solution was heated to 140° C. for 24 hours. After this time LC-MS indicated the complete cons... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary amine | Tertiary amine | null | C1COCC[NH]1 | c1ccc2cnncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | 140 | 0.083333 | CC(C)n1nc(Br)c2ccc(N)cc2c1=O.ClCCOCCCl>CN(C)C=O>CC(C)n1nc(Br)c2ccc(N3CCOCC3)cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa6e9f922f1048edb9296feef49ee84b | CC(C)n1nc(Br)c2ccc(N)cc2c1=O.NC(N)=O>>CC(C)n1nc(Br)c2ccc(O)cc2c1=O | S(O)(O)(=O)=O.S(O)(O)(=O)=O.NC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br.NC(=O)N.N(=O)[O-].[Na+]>>OC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br | N[c:11]1[cH:10][cH:9][c:8]2[c:6]([Br:7])[n:5][n:4]([CH:2]([CH3:1])[CH3:3])[c:15](=[O:16])[c:14]2[cH:13]1.NC(N)=[O:12]>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:13][c:14]2[c:15]1=[O:16] | CC(C)n1nc(Br)c2ccc(N)cc2c1=O.NC(N)=O | CC(C)n1nc(Br)c2ccc(O)cc2c1=O | null | null | O.CC(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | cfab2f484739552aa5b4f343f8242b28711d19942fda9cb68cb2f81405944162 | 891ec3b13223a598ccf2a9d11ebe28aad97dbcc6e0037050822ea9d225a1dca7 | O=c1[nH]ncc2ccccc12 | N-C(-N)=[O;H0;D1;+0:1].N-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]:[c:5]:[c;H0;D3;+0:2](-[OH;D1;+0:1]):[c:3]:[c:4] | 93.2 | [{"value": 93.0, "product": "OC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.2, "product": "OC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | Concentrated sulfuric acid (17 ml) was added slowly to a solution of 7-Amino-2-Isopropyl-4-bromo-2H-phthalazin-1-one (4.6 g, 0.016 mol) in HOAc (50 ml). The reaction mixture was cooled to 0° C. and a solution of NaNO2 (1.52 g, 0.022 mol) in water (10 ml) was added dropwise. The reaction mixture was stirred for a furthe... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Primary amine | Aromatic alcohol | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | Other | O.CC(=O)O | 0 | 0.333333 | CC(C)n1nc(Br)c2ccc(N)cc2c1=O.NC(N)=O>O.CC(=O)O>CC(C)n1nc(Br)c2ccc(O)cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9c3d5b01b17f4236980893f85881ff76 | CC(C)n1nc(Br)c2ccc(O)cc2c1=O.CI>>COc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | OC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br.C(=O)([O-])[O-].[K+].[K+].CI>>COC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br | [OH:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([Br:8])[n:9][n:10]([CH:11]([CH3:12])[CH3:13])[c:14](=[O:15])[c:16]2[cH:17]1.I[CH3:1]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([Br:8])[n:9][n:10]([CH:11]([CH3:12])[CH3:13])[c:14](=[O:15])[c:16]2[cH:17]1 | CC(C)n1nc(Br)c2ccc(O)cc2c1=O.CI | COc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | O=c1[nH]ncc2ccccc12 | I-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 76.9 | [{"value": 76.0, "product": "COC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.9, "product": "COC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of 7-hydroxy-2-Isopropyl-4-bromo-2H-phthalazin-1-one (0.4 g, 1.4 mmol) in THF (5 ml) were added successively, K2CO3 (0.59 g, 4.3 mmol) and methyl iodide (0.22 g, 1.55 mmol) and the mixture was heated to reflux for 24 hours. After this time, LC-MS indicated complete consumption of starting material... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccc2cnncc2c1 | HI | C1CCOC1 | null | null | CC(C)n1nc(Br)c2ccc(O)cc2c1=O.CI>C1CCOC1>COc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eece5d09bc8a41989485de88b56741c1 | CC(C)n1nc(Br)c2ccc(N)cc2c1=O>>CC(C)n1nc(Br)c2ccc(S)cc2c1=O | NC(=O)N.O(C(=S)[S-])CC.[K+].[OH-].[Na+].Cl.S(O)(O)(=O)=O.NC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br.N(=O)[O-].[Na+]>>SC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br | N[c:11]1[cH:10][cH:9][c:8]2[c:6]([Br:7])[n:5][n:4]([CH:2]([CH3:1])[CH3:3])[c:15](=[O:16])[c:14]2[cH:13]1>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([SH:12])[cH:13][c:14]2[c:15]1=[O:16] | CC(C)n1nc(Br)c2ccc(N)cc2c1=O | CC(C)n1nc(Br)c2ccc(S)cc2c1=O | null | null | O.CC(=O)O.C(Cl)Cl | Functional Group Interconversion | OtherReaction | ca2588dce952a1b38d55c09e7b0383f4664bdfa6a4f49cfbfbed4e37e3a612af | 87c716ea3b1c83749a8df825a73e64f71848c6f0dfcd36a842cec45d5ae0fe3c | O=c1[nH]ncc2ccccc12 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]:[c:4]:[c;H0;D3;+0:1](-[S;D1;H1:8]):[c:2]:[c:3] | 48.6 | [{"value": 48.0, "product": "SC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.6, "product": "SC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | Concentrated sulfuric acid (5 ml) was added dropwise to a solution of 7-amino-2-isopropyl-4-bromo-2H-phthalazin-1-one (1.5 g, 5.3 mmol) in HOAc (15 ml) and the solution was cooled to 0° C. A solution of NaNO2 (0.5 g, 7.4 mmol) in water (2.5 ml) was added dropwise and the reaction mixture was stirred at 0° C. for 20 min... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic thiol | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | null | O.CC(=O)O.C(Cl)Cl | 0 | 0.333333 | CC(C)n1nc(Br)c2ccc(N)cc2c1=O>O.CC(=O)O.C(Cl)Cl>CC(C)n1nc(Br)c2ccc(S)cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e5a6c44deaa44f9d8c92aa3671b9df28 | CC(C)n1nc(Br)c2ccc(S)cc2c1=O.CI>>CSc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | CI.SC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br.[H-].[Na+]>>CSC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br | [SH:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([Br:8])[n:9][n:10]([CH:11]([CH3:12])[CH3:13])[c:14](=[O:15])[c:16]2[cH:17]1.I[CH3:1]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([Br:8])[n:9][n:10]([CH:11]([CH3:12])[CH3:13])[c:14](=[O:15])[c:16]2[cH:17]1 | CC(C)n1nc(Br)c2ccc(S)cc2c1=O.CI | CSc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | thioether_nucl_sub | cbeef1e4b9250d05ec80fbfc2f139c184e610b2c8de8aec4214044a1d69bd441 | a20e50d7df818b91ffc2e826d304ad74f6246978a284c599e867e2d806b7437e | O=c1[nH]ncc2ccccc12 | I-[CH3;D1;+0:1].[SH;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[S;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 54 | [{"value": 54.0, "product": "CSC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.0, "product": "CSC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 7-mercap-to-2-isopropyl-4-bromo-2H-phthalazin-1-one (0.77 g, 2.6 mmol) in THF (8 ml), was added NaH (60%, 0.13 g, 3.1 mmol) portion-wise. After stirring for 5 min, methyl iodide (0.44 g, 3.1 mmol) was added dropwise and stirring was continued for four hours. The mixture was concentrated under vacuum an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol | Monosulfide | null | null | c1ccc2cnncc2c1 | HI | C1CCOC1 | null | 0.083333 | CC(C)n1nc(Br)c2ccc(S)cc2c1=O.CI>C1CCOC1>CSc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-385fb057eda2459ba0712eb41836fdce | CSc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1>>Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(S(C)(=O)=O)ccc23)n[nH]1 | OOS(=O)[O-].[K+].C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)SC)=O.O1CCOCC1.O>>C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)S(=O)(=O)C)=O | [CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8]([CH:9]([CH3:10])[CH3:11])[c:12](=[O:13])[c:14]3[cH:15][c:16]([S:17][CH3:18])[cH:21][cH:22][c:23]23)[n:24][nH:25]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8]([CH:9]([CH3:10])[CH3:11])[c:12](=[O:13])[c:14]3[cH:15][c:16]([S:17]([CH3:18])(=[O:19])=[O:20])[cH:21][cH:22][... | CSc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1 | Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(S(C)(=O)=O)ccc23)n[nH]1 | null | null | O | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | O=c1[nH]nc(Nc2cc[nH]n2)c2ccccc12 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[C;D1;H3:1]-[S;H0;D4;+0:2](=[O;D1;H0:6])(=[O;D1;H0:7])-[c:3](:[c:4]):[c:5] | 25 | [{"value": 25.0, "product": "C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)S(=O)(=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Oxone (0.88 g, 1.4 mmol) was added in one portion to a stirred solution of 2-iso-propyl-4-(5-methyl-1H-pyrazol-3-ylamino)-7-methylsulfanyl-2H-phthalazin-1-one (0.12 g, 0.36 mmol) in a 4:1 mixture of dioxane/water (1.2 ml) and the reaction mixture was stirred at RT for one hour. The reaction mixture was diluted with wat... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1cn[nH]c1.c1ccc2cnncc2c1 | null | O | null | 1 | CSc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1>O>Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(S(C)(=O)=O)ccc23)n[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aef2170197764f63b3a6bd3bcd78ba7e | CNc1ccc2c(Br)nn(C(C)C)c(=O)c2c1.ClCCN1CCOCC1>>CC(C)n1nc(Br)c2ccc(N(C)CCN3CCOCC3)cc2c1=O | O.ClCCN1CCOCC1.BrC1=NN(C(C2=CC(=CC=C12)NC)=O)C(C)C.[H-].[Na+]>>BrC1=NN(C(C2=CC(=CC=C12)N(CCN1CCOCC1)C)=O)C(C)C | [CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([NH:12][CH3:13])[cH:22][c:23]2[c:24]1=[O:25].Cl[CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([N:12]([CH3:13])[CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][O:19][CH2... | CNc1ccc2c(Br)nn(C(C)C)c(=O)c2c1.ClCCN1CCOCC1 | CC(C)n1nc(Br)c2ccc(N(C)CCN3CCOCC3)cc2c1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=c1[nH]ncc2ccc(NCCN3CCOCC3)cc12 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[C;D1;H3:4]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:5](-[C;D1;H3:4])-[c:6](:[c:7]):[c:8] | 30 | [{"value": 30.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)N(CCN1CCOCC1)C)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.3, "product": "BrC1=NN(C(C2=CC(=CC=C12)N(CCN1CCOCC1)C)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 4-Bromo-2-isopropyl-7-methylamino-2H-phthalazin-1-one (0.13 g, 0.44 mmol) was dissolved in DMF (5 ml). To this was added NaH (60%, 0.053 g, 1.3 mmol) as a suspension in DMF (2 ml). The mixture was stirred at RT for 30 min then 4-(2-chloro-ethyl)-morpholine (0.12 g, 0.66 mmol) was added in one portion as a solution in D... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccc2cnncc2c1.C1COCC[NH]1 | HCl | CN(C)C=O | null | 0.5 | CNc1ccc2c(Br)nn(C(C)C)c(=O)c2c1.ClCCN1CCOCC1>CN(C)C=O>CC(C)n1nc(Br)c2ccc(N(C)CCN3CCOCC3)cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c7043891c3154eb2a99d8c1382fa8984 | CC(C)n1nc(Br)c2ccc(N)cc2c1=O.CN=C=O>>CNC(=O)Nc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | NC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br.[H-].[Na+].CN=C=O>>BrC1=NN(C(C2=CC(=CC=C12)NC(=O)NC)=O)C(C)C | [NH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([Br:11])[n:12][n:13]([CH:14]([CH3:15])[CH3:16])[c:17](=[O:18])[c:19]2[cH:20]1.[CH3:1][N:2]=[C:3]=[O:4]>>[CH3:1][NH:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([Br:11])[n:12][n:13]([CH:14]([CH3:15])[CH3:16])[c:17](=[O:18])[c:19]2[cH:20]1 | CC(C)n1nc(Br)c2ccc(N)cc2c1=O.CN=C=O | CNC(=O)Nc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | null | null | C1CCOC1 | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=c1[nH]ncc2ccccc12 | [C;D1;H3:1]-[N;H0;D2;+0:2]=[C;H0;D2;+0:3]=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:1]-[NH;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 78.3 | [{"value": 78.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)NC(=O)NC)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.3, "product": "BrC1=NN(C(C2=CC(=CC=C12)NC(=O)NC)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | 7-Amino-2-Isopropyl-4-bromo-2H-phthalazin-1-one (0.5 g, 1.77 mmol) was dissolved in THF (5 ml). To this was added NaH (60%, 0.14 g, 3.54 mmol) as a suspension in THF (2 ml) and the reaction mixture was stirred for 5 min. After this time methyl isocyanate (0.2 g, 3.55 mmol) was added in one portion and the reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2cnncc2c1 | null | C1CCOC1 | null | 0.083333 | CC(C)n1nc(Br)c2ccc(N)cc2c1=O.CN=C=O>C1CCOC1>CNC(=O)Nc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d0f23005a0142b0931500d5b443f3f2 | NN.O=C(O)c1ccc2c(c1)C(=O)OC2=O>>O=C(O)c1ccc2c(=O)[nH][nH]c(=O)c2c1 | O.NN.C1=CC2=C(C=C1C(=O)O)C(=O)OC2=O>>O=C1NNC(C2=CC(=CC=C12)C(=O)O)=O | [NH2:10][NH2:11].O1[C:8](=[O:9])[c:7]2[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:15][c:14]2[C:12]1=[O:13]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8](=[O:9])[nH:10][nH:11][c:12](=[O:13])[c:14]2[cH:15]1 | NN.O=C(O)c1ccc2c(c1)C(=O)OC2=O | O=C(O)c1ccc2c(=O)[nH][nH]c(=O)c2c1 | null | null | CC(=O)O | Miscellaneous | OtherReaction | 2eb41fd326d947b9a686dc388415f2cdee10671cc3d0a161b79e11b60824f49e | 7bb342cf852a2f6fefb018a30606d65eee2249c97e82671b7539980b110d9a4f | O=c1[nH][nH]c(=O)c2ccccc12 | [NH2;D1;+0:1]-[NH2;D1;+0:2].[O;D1;H0:3]=[C;H0;D3;+0:4]1-O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9]-1:[c:10]>>[O;D1;H0:3]=[c;H0;D3;+0:4]1:[nH;D2;+0:2]:[nH;D2;+0:1]:[c;H0;D3;+0:5](=[O;D1;H0:6]):[c:7](:[c:8]):[c:9]:1:[c:10] | 85 | [{"value": 85.0, "product": "O=C1NNC(C2=CC(=CC=C12)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.9, "product": "O=C1NNC(C2=CC(=CC=C12)C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | Hydrazine hydrate (26 g, 0.52 mol) was added in one portion to a stirred mixture of 1,2,4-benzenetricarboxylic anhydride (100 g, 0.52 mol), in HOAc (1.0 L) at RT. The mixture was heated to 120° C. for 2 hours and then allowed to cool to RT. The solid was filtered, washed with water (250 ml) and dried in the vacuum oven... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Anhydride.Ester.Ester | null | c1ccc2c(c1)COC2 | C1=c2ccccc2=CNN1 | C1=c2ccccc2=CNN1 | HO- | CC(=O)O | 120 | null | NN.O=C(O)c1ccc2c(c1)C(=O)OC2=O>CC(=O)O>O=C(O)c1ccc2c(=O)[nH][nH]c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cbb317f0084440759e4678e33cddf86b | CCO.O=C(O)c1ccc2c(Br)n[nH]c(=O)c2c1>>CCOC(=O)c1ccc2c(Br)n[nH]c(=O)c2c1 | S(O)(O)(=O)=O.BrC1=NNC(C2=CC(=CC=C12)C(=O)O)=O.CCO>>C(C)OC(=O)C=1C=C2C(NN=C(C2=CC1)Br)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([Br:11])[n:12][nH:13][c:14](=[O:15])[c:16]2[cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([Br:11])[n:12][nH:13][c:14](=[O:15])[c:16]2[cH:17]1 | CCO.O=C(O)c1ccc2c(Br)n[nH]c(=O)c2c1 | CCOC(=O)c1ccc2c(Br)n[nH]c(=O)c2c1 | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=c1[nH]ncc2ccccc12 | 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] | 31 | [{"value": 31.0, "product": "C(C)OC(=O)C=1C=C2C(NN=C(C2=CC1)Br)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Concentrated sulfuric acid (40 ml) was added to a stirred solution of 1-Bromo-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid (85 g, 0.32 mol) in EtOH (500 ml) and the mixture was heated to reflux for 48 hours. After this time, the reaction mixture was cooled and the resulting precipitate was filtered. The precipitate ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccc2cnncc2c1 | HO- | null | null | null | CCO.O=C(O)c1ccc2c(Br)n[nH]c(=O)c2c1>>CCOC(=O)c1ccc2c(Br)n[nH]c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cfe9c22ebc4644fba436418c9b12ca56 | CC(Br)CO.CCOC(=O)c1ccc2c(Br)n[nH]c(=O)c2c1>>CCOC(=O)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | BrC(CO)C.C(C)OC(=O)C=1C=C2C(NN=C(C2=CC1)Br)=O.[H-].[Na+]>>C(C)OC(=O)C=1C=C2C(N(N=C(C2=CC1)Br)C(C)C)=O | O[CH2:16][CH:14](Br)[CH3:15].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([Br:11])[n:12][nH:13][c:17](=[O:18])[c:19]2[cH:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([Br:11])[n:12][n:13]([CH:14]([CH3:15])[CH3:16])[c:17](=[O:18])[c:19]2[cH:20]1 | CC(Br)CO.CCOC(=O)c1ccc2c(Br)n[nH]c(=O)c2c1 | CCOC(=O)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b13ee664a48205e8588ba2fe6c931f068eed8e0710341d0557b6e0be4fe35def | 2134b0ddabf7bc32ccd75d1ac86b03077ce2dab15f2fd4840f21221cbfe820dd | O=c1[nH]ncc2ccccc12 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-O.[O;D1;H0:4]=[c:5](:[c:6]):[nH;D2;+0:7]:[#7;a:8]:[c:9]>>[C;D1;H3:2]-[CH;D3;+0:1](-[CH3;D1;+0:3])-[n;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:5](=[O;D1;H0:4]):[c:6] | 34 | [{"value": 34.0, "product": "C(C)OC(=O)C=1C=C2C(N(N=C(C2=CC1)Br)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.9, "product": "C(C)OC(=O)C=1C=C2C(N(N=C(C2=CC1)Br)C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Bromo-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester (6 g, 0.02 mol) was dissolved in DMF (60 ml). To this was added NaH (60%, 0.97 g, 0.024 mol) as a DMF suspension (5 ml). The mixture was stirred at RT for 30 min then 2-bromo-propanol (3.7 g, 0.03 mol) was added in one portion as a solution in DMF (5 ml)... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary alcohol | null | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | HBr | CN(C)C=O | null | 0.5 | CC(Br)CO.CCOC(=O)c1ccc2c(Br)n[nH]c(=O)c2c1>CN(C)C=O>CCOC(=O)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-866127e293914165a8ab8b3a807a9b0f | CCOC(=O)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1>>CC(C)n1nc(Br)c2ccc(CO)cc2c1=O | [NH4+].[Cl-].[Li+].[BH4-].C(C)OC(=O)C=1C=C2C(N(N=C(C2=CC1)Br)C(C)C)=O.[Li+].[BH4-]>>BrC1=NN(C(C2=CC(=CC=C12)CO)=O)C(C)C | CCO[C:12]([c:11]1[cH:10][cH:9][c:8]2[c:6]([Br:7])[n:5][n:4]([CH:2]([CH3:1])[CH3:3])[c:16](=[O:17])[c:15]2[cH:14]1)=[O:13]>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([CH2:12][OH:13])[cH:14][c:15]2[c:16]1=[O:17] | CCOC(=O)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | CC(C)n1nc(Br)c2ccc(CO)cc2c1=O | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=c1[nH]ncc2ccccc12 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 44.5 | [{"value": 43.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)CO)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.5, "product": "BrC1=NN(C(C2=CC(=CC=C12)CO)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 24 | HOUR | Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester (2.3 g, 6.8 mmol) was suspended in THF (50 ml) and cooled to 0° C. To the suspension was added LiBH4 (5.1 ml of a 2M solution in THF, 10.2 mmol) dropwise, the suspension was allowed to warm to RT and stirred for 24 hours. After this time, LC-... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2cnncc2c1 | HO- | C1CCOC1 | 0 | 24 | CCOC(=O)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1>C1CCOC1>CC(C)n1nc(Br)c2ccc(CO)cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b4c14feb9c614272842705abd1c6a541 | CC(C)n1nc(Br)c2ccc(CO)cc2c1=O.CI>>COCc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | BrC1=NN(C(C2=CC(=CC=C12)CO)=O)C(C)C.[H-].[Na+].CI>>BrC1=NN(C(C2=CC(=CC=C12)COC)=O)C(C)C | [OH:2][CH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([Br:9])[n:10][n:11]([CH:12]([CH3:13])[CH3:14])[c:15](=[O:16])[c:17]2[cH:18]1.I[CH3:1]>>[CH3:1][O:2][CH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([Br:9])[n:10][n:11]([CH:12]([CH3:13])[CH3:14])[c:15](=[O:16])[c:17]2[cH:18]1 | CC(C)n1nc(Br)c2ccc(CO)cc2c1=O.CI | COCc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 31b37b19ff6de58cf584e89bae19f862b01d058b473835fea10bbd4c0a53fd14 | f3e76c16e7df5a83f618c93f8745117d548e410efce45e89753f2c180a9b20f8 | O=c1[nH]ncc2ccccc12 | I-[CH3;D1;+0:1].[OH;D1;+0:2]-[C:3]-[c:4]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[C:3]-[c:4] | 69.5 | [{"value": 69.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)COC)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.5, "product": "BrC1=NN(C(C2=CC(=CC=C12)COC)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | 4-Bromo-7-hydroxymethyl-2-isopropyl-2H-phthalazin-1-one (0.11 g, 0.37 mmol) was dissolved in THF (2 ml). To this was added NaH (60%, 0.019 g, 0.44 mmol) as a THF suspension (2 ml). To this was added methyl iodide (0.063 g, 0.48 mmol) and the reaction mixture was stirred for 20 hours. The reaction mixture was concentrat... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Ether | null | null | c1ccc2cnncc2c1 | HI | C1CCOC1 | null | 20 | CC(C)n1nc(Br)c2ccc(CO)cc2c1=O.CI>C1CCOC1>COCc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-02daeccc312a4d1cbe22a79517ab5588 | CC(C)n1nc(Br)c2ccc(CO)cc2c1=O.[Br-]>>CC(C)n1nc(Br)c2ccc(CBr)cc2c1=O | BrC1=NN(C(C2=CC(=CC=C12)CO)=O)C(C)C.C[Si](C)(C)Br.[Li+].[Br-]>>BrC1=NN(C(C2=CC(=CC=C12)CBr)=O)C(C)C | O[CH2:12][c:11]1[cH:10][cH:9][c:8]2[c:6]([Br:7])[n:5][n:4]([CH:2]([CH3:1])[CH3:3])[c:16](=[O:17])[c:15]2[cH:14]1.[Br-:13]>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([CH2:12][Br:13])[cH:14][c:15]2[c:16]1=[O:17] | CC(C)n1nc(Br)c2ccc(CO)cc2c1=O.[Br-] | CC(C)n1nc(Br)c2ccc(CBr)cc2c1=O | null | null | CC#N | Functional Group Interconversion | OtherReaction | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | O=c1[nH]ncc2ccccc12 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[Br-;H0;D0:5]>>[Br;H0;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 44.4 | [{"value": 44.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)CBr)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.4, "product": "BrC1=NN(C(C2=CC(=CC=C12)CBr)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A solution of 4-bromo-7-hydroxymethyl-2-isopropyl-2H-phthalazin-1-one (0.74 g, 2.5 mmol) in MeCN (5 ml) was added dropwise to a stirred suspension of trimethylsilyl bromide (TMSBr) (0.9 g, 6.3 mmol) and LiBr (0.41 g, 5 mmol) in MeCN (15 ml). The reaction mixture was heated to 80° C. for 24 hours, after which time the r... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccc2cnncc2c1 | HO- | CC#N | 80 | null | CC(C)n1nc(Br)c2ccc(CO)cc2c1=O.[Br-]>CC#N>CC(C)n1nc(Br)c2ccc(CBr)cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef186c37fc114633ac7ebc7c23f639f4 | CC(C)n1nc(Br)c2ccc(CBr)cc2c1=O.CN1CCNCC1>>CC(C)n1nc(Br)c2ccc(CN3CCN(C)CC3)cc2c1=O | BrC1=NN(C(C2=CC(=CC=C12)CBr)=O)C(C)C.CN1CCNCC1>>BrC1=NN(C(C2=CC(=CC=C12)CN1CCN(CC1)C)=O)C(C)C | Br[CH2:12][c:11]1[cH:10][cH:9][c:8]2[c:6]([Br:7])[n:5][n:4]([CH:2]([CH3:1])[CH3:3])[c:22](=[O:23])[c:21]2[cH:20]1.[NH:13]1[CH2:14][CH2:15][N:16]([CH3:17])[CH2:18][CH2:19]1>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([CH2:12][N:13]3[CH2:14][CH2:15][N:16]([CH3:17])[CH2:18][CH2:19]3)[cH:20][c:... | CC(C)n1nc(Br)c2ccc(CBr)cc2c1=O.CN1CCNCC1 | CC(C)n1nc(Br)c2ccc(CN3CCN(C)CC3)cc2c1=O | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=c1[nH]ncc2ccc(CN3CCNCC3)cc12 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1):[c:4] | 84 | [{"value": 84.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)CN1CCN(CC1)C)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)CN1CCN(CC1)C)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 4-Bromo-7-bromomethyl-2-isopropyl-2H-phthalazin-1-one (0.2 g, 0.56 mmol) was dissolved in THF (1 ml), to this was added N-methyl piperazine (0.14 g, 1.4 mmol) as a solution in THF (1 ml) and the reaction mixture was stirred for 1 hour. Whereupon LC-MS indicated complete consumption of starting material, the solvent was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2cnncc2c1.C1C[NH]CC[NH]1 | HBr | C1CCOC1 | null | 1 | CC(C)n1nc(Br)c2ccc(CBr)cc2c1=O.CN1CCNCC1>C1CCOC1>CC(C)n1nc(Br)c2ccc(CN3CCN(C)CC3)cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f1a70e7a2be4443788607e2c2a0efd53 | Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(C(C)(C)O[SiH2]C(C)(C)C)ccc23)nn1C(=O)OC(C)(C)C>>Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(CO)ccc23)nn1C(=O)OC(C)(C)C | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(C)(C)OC(=O)N1N=C(C=C1C)N(C1=NN(C(C2=CC(=CC=C12)C(O[SiH2]C(C)(C)C)(C)C)=O)C(C)C)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1N=C(C=C1C)N(C1=NN(C(C2=CC(=CC=C12)CO)=O)C(C)C)C(=O)OC(C)(C)C | CC(C)(C)[SiH2][O:25][C:24](C)(C)[c:23]1[cH:22][c:21]2[c:19](=[O:20])[n:15]([CH:16]([CH3:17])[CH3:18])[n:14][c:13]([N:5]([c:4]3[cH:3][c:2]([CH3:1])[n:30]([C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[n:29]3)[C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[c:28]2[cH:27][cH:26]1>>[CH3:1][c:2]1[cH:3][c:4]([N... | Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(C(C)(C)O[SiH2]C(C)(C)C)ccc23)nn1C(=O)OC(C)(C)C | Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(CO)ccc23)nn1C(=O)OC(C)(C)C | null | null | C1CCOC1 | Deprotection | OtherReaction | d7487e9652d81f9226fa8fb90bf02725deb1441d4abc97ee4fdbe439e00122e0 | ff9889ffd40f59bd281424811967f384d29acb01a2d54e10590c5a677f81d17a | O=c1[nH]nc(Nc2cc[nH]n2)c2ccccc12 | C-C(-C)(-C)-[SiH2]-[O;H0;D2;+0:1]-[C;H0;D4;+0:2](-C)(-C)-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 60.7 | [{"value": 45.0, "product": "C(C)(C)(C)OC(=O)N1N=C(C=C1C)N(C1=NN(C(C2=CC(=CC=C12)CO)=O)C(C)C)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.7, "product": "C(C)(C)(C)OC(=O)N1N=C(C=C1C)N(C1=NN(C(C2=CC(=CC=C12)CO)=O)C(C)C)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | 24 | HOUR | 3-{tert-Butoxycarbonyl-[6-(tert-butyl-dimethyl-silanyloxymethyl)-3-isopropyl-4-oxo-3,4-dihydro-phthalazin-1-yl]-amino}-5-methyl-pyrazole-1-carboxylic acid tert-butyl ester (0.78, 1.25 mmol) was dissolved in THF (3 ml), to this was added a 1M solution of tetrabutylammonium fluoride (TBAF) in THF (1.87 ml, 1.87 mmol) and... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | null | null | c1cc[nH]n1.c1ccc2cnncc2c1 | Other | C1CCOC1 | null | 24 | Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(C(C)(C)O[SiH2]C(C)(C)C)ccc23)nn1C(=O)OC(C)(C)C>C1CCOC1>Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(CO)ccc23)nn1C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e7325eba3805489c9300d96143e6601c | Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(CO)ccc23)nn1C(=O)OC(C)(C)C.O=C(O)c1ccccc1I(=O)=O>>Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(C(=O)O)ccc23)nn1C(=O)OC(C)(C)C | Cl(=O)[O-].[Na+].S(N)(O)(=O)=O.C(C)(C)(C)OC(=O)N1N=C(C=C1C)N(C1=NN(C(C2=CC(=CC=C12)CO)=O)C(C)C)C(=O)OC(C)(C)C.I(=O)(=O)C1=C(C(=O)O)C=CC=C1>>C(C)(C)(C)OC(=O)N(C1=NN(C(C2=CC(=CC=C12)C(=O)O)=O)C(C)C)C1=NN(C(=C1)C)C(=O)OC(C)(C)C | [CH3:1][c:2]1[cH:3][c:4]([N:5]([C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[c:13]2[n:14][n:15]([CH:16]([CH3:17])[CH3:18])[c:19](=[O:20])[c:21]3[cH:22][c:23]([CH2:24][OH:26])[cH:27][cH:28][c:29]23)[n:30][n:31]1[C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38].O=I(=O)c1ccccc1C(O)=[O:25]>>[CH3:1][c:2]1[cH:3]... | Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(CO)ccc23)nn1C(=O)OC(C)(C)C.O=C(O)c1ccccc1I(=O)=O | Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(C(=O)O)ccc23)nn1C(=O)OC(C)(C)C | null | null | O.CS(=O)C.C(Cl)Cl | Miscellaneous | OtherReaction | 4b8aa669cd30364b925ec9aa884128ecdc78480edb5ee6f55be0a39a277c0e54 | 4c0bee2a32eec97eb662589f8993ee5133fee245b98f7b691d89a3f3c7cd5676 | O=c1[nH]nc(Nc2cc[nH]n2)c2ccccc12 | O-C(=[O;H0;D1;+0:1])-c1:c:c:c:c:c:1-I(=O)=O.[O;D1;H1:2]-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H1:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4](:[c:5]):[c:6] | 44 | [{"value": 44.0, "product": "C(C)(C)(C)OC(=O)N(C1=NN(C(C2=CC(=CC=C12)C(=O)O)=O)C(C)C)C1=NN(C(=C1)C)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.8, "product": "C(C)(C)(C)OC(=O)N(C1=NN(C(C2=CC(=CC=C12)C(=O)O)=O)C(C)C)C1=NN(C(=C1)C)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is... | null | null | 24 | HOUR | 3-[tert-Butoxycarbonyl-(6-hydroxymethyl-3-isopropyl-4-oxo-3,4-dihydro-phthalazin-1-yl)-amino]-5-methyl-pyrazole-1-carboxylic acid tert-butyl ester (0.2 g, 0.39 mmol) was dissolved in DMSO (3 ml). To this was added 2-iodoxybenzoic acid (IBX) (0.22 g, 0.78 mmol) in one portion and the reaction mixture was stirred at RT f... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Primary alcohol | Carboxylic acid | c1ccccc1 | null | c1cc[nH]n1.c1ccc2cnncc2c1 | HI | O.CS(=O)C.C(Cl)Cl | null | 24 | Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(CO)ccc23)nn1C(=O)OC(C)(C)C.O=C(O)c1ccccc1I(=O)=O>O.CS(=O)C.C(Cl)Cl>Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(C(=O)O)ccc23)nn1C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d2a1829b0ff74d888e124005d86356a3 | Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(C(=O)O)ccc23)nn1C(=O)OC(C)(C)C>>Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(C(=O)O)ccc23)n[nH]1 | C(C)(C)(C)OC(=O)N(C1=NN(C(C2=CC(=CC=C12)C(=O)O)=O)C(C)C)C1=NN(C(=C1)C)C(=O)OC(C)(C)C>>C(C)(C)N1N=C(C2=CC=C(C=C2C1=O)C(=O)O)NC1=NNC(=C1)C | CC(C)(C)OC(=O)[N:5]([c:4]1[cH:3][c:2]([CH3:1])[n:24](C(=O)OC(C)(C)C)[n:23]1)[c:6]1[n:7][n:8]([CH:9]([CH3:10])[CH3:11])[c:12](=[O:13])[c:14]2[cH:15][c:16]([C:17](=[O:18])[OH:19])[cH:20][cH:21][c:22]12>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8]([CH:9]([CH3:10])[CH3:11])[c:12](=[O:13])[c:14]3[cH:15][c:16]([C:17](=[O... | Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(C(=O)O)ccc23)nn1C(=O)OC(C)(C)C | Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(C(=O)O)ccc23)n[nH]1 | null | null | C(=O)(C(F)(F)F)O.C(Cl)Cl | Reduction | OtherReaction | a4215d4df0b5986227f28cfb68f70f46bb429d0e8679bdb32fdf15f656c22052 | b6e7823586033bfbc03f4d0c8dc7543754c419d00fed6ec047b5fd9adf5eea30 | O=c1[nH]nc(Nc2cc[nH]n2)c2ccccc12 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[c:2]1:[#7;a:3]:[n;H0;D3;+0:4](-C(=O)-O-C(-C)(-C)-C):[c:5](-[C;D1;H3:6]):[c:7]:1)-[c:8](:[c:9]):[#7;a:10]:[#7;a:11](-[C:12]):[c:13]>>[C:12]-[#7;a:11](:[c:13]):[#7;a:10]:[c:8](-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[nH;D2;+0:4]:[c:5](-[C;D1;H3:6]):[c:7]:1):[c:9] | null | [] | null | null | 48 | HOUR | 1-[tert-Butoxycarbonyl-(1-tert-butoxycarbonyl-5-methyl-1H-pyrazol-3-yl)-amino]-3-isopropyl-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid (13.0 mg, 0.02 mmol) was dissolved in a 20% TFA/DCM solution (2 ml) and the reaction mixture was stirred for 48 hours. After this time, the reaction mixture was concentrated and the... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Boc.Boc | Secondary amine | c1cc[nH]n1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2cnncc2c1 | HO- | C(=O)(C(F)(F)F)O.C(Cl)Cl | null | 48 | Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(C(=O)O)ccc23)nn1C(=O)OC(C)(C)C>C(=O)(C(F)(F)F)O.C(Cl)Cl>Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(C(=O)O)ccc23)n[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-846d033a5567476b9e3db8735ab280f3 | C1COCCN1.Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(C(=O)O)ccc23)nn1C(=O)OC(C)(C)C>>Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(C(=O)N4CCOCC4)ccc23)n[nH]1 | C(C)(C)(C)OC(=O)N(C1=NN(C(C2=CC(=CC=C12)C(=O)O)=O)C(C)C)C1=NN(C(=C1)C)C(=O)OC(C)(C)C.N1CCOCC1.F[B-](F)(F)F.N1(N=NC2=C1C=CC=C2)OC(=[N+](C)C)N(C)C>>C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)C(=O)N1CCOCC1)=O | [NH:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1.CC(C)(C)OC(=O)[N:5]([c:4]1[cH:3][c:2]([CH3:1])[n:29](C(=O)OC(C)(C)C)[n:28]1)[c:6]1[n:7][n:8]([CH:9]([CH3:10])[CH3:11])[c:12](=[O:13])[c:14]2[cH:15][c:16]([C:17](O)=[O:18])[cH:25][cH:26][c:27]12>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8]([CH:9]([CH3:10])[CH3:11])[c:1... | C1COCCN1.Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(C(=O)O)ccc23)nn1C(=O)OC(C)(C)C | Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(C(=O)N4CCOCC4)ccc23)n[nH]1 | null | null | C(=O)(C(F)(F)F)O.C(Cl)Cl.CN(C)C=O | Acylation | OtherReaction | 2d2df448559efacfe483701200e87d8676e9059a957f4a66ee9ca853a9308e10 | dbaba5af57f77ad662016a18f28600679c02f082ca5a0998a13d94ae8dea4729 | O=C(c1ccc2c(Nc3cc[nH]n3)n[nH]c(=O)c2c1)N1CCOCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[c:2]1:[#7;a:3]:[n;H0;D3;+0:4](-C(=O)-O-C(-C)(-C)-C):[c:5](-[C;D1;H3:6]):[c:7]:1)-[c:8](:[c:9]):[#7;a:10]:[#7;a:11](-[C:12]):[c:13].O-[C;H0;D3;+0:14](=[O;D1;H0:15])-[c:16](:[c:17]):[c:18].[#8:19]1-[C:20]-[C:21]-[NH;D2;+0:22]-[C:23]-[C:24]-1>>[C:12]-[#7;a:11](:[c:13]):[#7;a:10]:[c:8](... | null | [] | 0 | CELSIUS | 24 | HOUR | 1-[tert-Butoxycarbonyl-(1-tert-butoxycarbonyl-5-methyl-1H-pyrazol-3-yl)-amino]-3-isopropyl-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid (13 mg, 0.025 mmol) was dissolved in DMF (2 ml). To this was added morpholine (6.4 mg, 0.075 mmol) and the reaction mixture was cooled to 0° C., 2-(1H-Benzotriazole-1-yl)-1,1,3,3-te... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Ether.Secondary amine.Boc.Boc | Tertiary amide.Secondary amine | C1COCCN1.c1cc[nH]n1 | c1cn[nH]c1.C1COCC[NH]1 | c1cn[nH]c1.c1ccc2cnncc2c1.C1COCC[NH]1 | HO- | C(=O)(C(F)(F)F)O.C(Cl)Cl.CN(C)C=O | 0 | 24 | C1COCCN1.Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(C(=O)O)ccc23)nn1C(=O)OC(C)(C)C>C(=O)(C(F)(F)F)O.C(Cl)Cl.CN(C)C=O>Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(C(=O)N4CCOCC4)ccc23)n[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-43a76ec34c624da5a3adf1c809658702 | CI.Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(C(=O)O)ccc23)nn1C(=O)OC(C)(C)C>>COC(=O)c1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1 | C(C)(C)(C)OC(=O)N(C1=NN(C(C2=CC(=CC=C12)C(=O)O)=O)C(C)C)C1=NN(C(=C1)C)C(=O)OC(C)(C)C.C(=O)([O-])[O-].[K+].[K+].CI>>COC(=O)C=1C=C2C(N(N=C(C2=CC1)NC1=NNC(=C1)C)C(C)C)=O | I[CH3:1].CC(C)(C)OC(=O)[N:10]([c:9]1[c:8]2[cH:7][cH:6][c:5]([C:3]([OH:2])=[O:4])[cH:25][c:24]2[c:22](=[O:23])[n:18]([CH:19]([CH3:20])[CH3:21])[n:17]1)[c:11]1[cH:12][c:13]([CH3:14])[n:15](C(=O)OC(C)(C)C)[n:16]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([NH:10][c:11]3[cH:12][c:13]([CH3:14])[nH:15][n:16]3)[n... | CI.Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(C(=O)O)ccc23)nn1C(=O)OC(C)(C)C | COC(=O)c1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | f95c6fa735c9028d9b63eeafad85fb95ff0b995b439af927d966180112d45546 | 53127ac04428c936ced305619a8078ffed9829d013ee3e724480da031b5c110a | O=c1[nH]nc(Nc2cc[nH]n2)c2ccccc12 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[c:2]1:[#7;a:3]:[n;H0;D3;+0:4](-C(=O)-O-C(-C)(-C)-C):[c:5](-[C;D1;H3:6]):[c:7]:1)-[c:8](:[c:9]):[#7;a:10]:[#7;a:11](-[C:12]):[c:13].[O;D1;H0:14]=[C:15](-[OH;D1;+0:16])-[c:17].I-[CH3;D1;+0:18]>>[CH3;D1;+0:18]-[O;H0;D2;+0:16]-[C:15](=[O;D1;H0:14])-[c:17].[C:12]-[#7;a:11](:[c:13]):[#7;a... | null | [] | null | null | 30 | MINUTE | 1-[tert-Butoxycarbonyl-(1-tert-butoxycarbonyl-5-methyl-1H-pyrazol-3-yl)-amino] -3-iso-propyl-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid (10 mg, 0.019 mmol) (Intermediate of Example M-1) was dissolved in DCM (1 ml). To this was added K2CO3 (3.1 mg, 0.028 mmol) followed by methyl iodide (3.3 mg, 0.028 mmol) and the ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Ether.Boc.Boc | Ester.Secondary amine | c1cc[nH]n1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccc2cnncc2c1 | HI | C(Cl)Cl | null | 0.5 | CI.Cc1cc(N(C(=O)OC(C)(C)C)c2nn(C(C)C)c(=O)c3cc(C(=O)O)ccc23)nn1C(=O)OC(C)(C)C>C(Cl)Cl>COC(=O)c1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d2e6c783f16f46398ced01d2a8d851dd | COCCN1NC(Br)(Br)c2ccccc2C1=O.Cc1cc(N)n(C(C)(C)C)n1>>COCCn1nc(Nc2cc(C)nn2C(C)(C)C)c2ccccc2c1=O | BrC1(NN(C(C2=CC=CC=C12)=O)CCOC)Br.C(C)(C)(C)N1N=C(C=C1N)C.C(=O)([O-])[O-].[Cs+].[Cs+].C1(=CC=CC=C1)P(C1=CC=CC=2C(C3=CC=CC(=C3OC12)P(C1=CC=CC=C1)C1=CC=CC=C1)(C)C)C1=CC=CC=C1>>C(C)(C)(C)N1N=C(C=C1NC1=NN(C(C2=CC=CC=C12)=O)CCOC)C | Br[C:7]1(Br)[NH:6][N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:25](=[O:26])[c:24]2[c:19]1[cH:20][cH:21][cH:22][cH:23]2.[NH2:8][c:9]1[cH:10][c:11]([CH3:12])[n:13][n:14]1[C:15]([CH3:16])([CH3:17])[CH3:18]>>[CH3:1][O:2][CH2:3][CH2:4][n:5]1[n:6][c:7]([NH:8][c:9]2[cH:10][c:11]([CH3:12])[n:13][n:14]2[C:15]([CH3:16])([CH3:17])[CH3:18]... | COCCN1NC(Br)(Br)c2ccccc2C1=O.Cc1cc(N)n(C(C)(C)C)n1 | COCCn1nc(Nc2cc(C)nn2C(C)(C)C)c2ccccc2c1=O | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O1CCOCC1.O | Protection | OtherReaction | 6568a3f99999b1d06d7bce2b306949027d75dccdb355515b33169362b38e2520 | 6b3e7409526833949cd1cabc365be823256728f8bca1489e91cac13b7df64018 | O=c1[nH]nc(Nc2ccn[nH]2)c2ccccc12 | Br-[C;H0;D4;+0:1]1(-Br)-[NH;D2;+0:2]-[N;H0;D3;+0:3](-[C:4]-[C:5])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11].[C:12]-[#7;a:13]1:[#7;a:14]:[c:15]:[c:16]:[c:17]:1-[NH2;D1;+0:18]>>[C:12]-[#7;a:13]1:[#7;a:14]:[c:15]:[c:16]:[c:17]:1-[NH;D2;+0:18]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[n;H0;D3;+0:3](-[C:4]-[C:5]):[c;... | 65 | [{"value": 65.0, "product": "C(C)(C)(C)N1N=C(C=C1NC1=NN(C(C2=CC=CC=C12)=O)CCOC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.7, "product": "C(C)(C)(C)N1N=C(C=C1NC1=NN(C(C2=CC=CC=C12)=O)CCOC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 8 | HOUR | 4-Bromo-2-(2-methoxyethyl)-4-bromo-2H-phthalazin-1-one (0.57 g, 2.0 mmol), 1-(tert-butyl)-3-methyl-1H-pyrazol-5-ylamine (0.46 g, 3.0 mmol), Cs2CO3 (0.98 mg, 3.0 mmol), tris(dibenzylideneacetone)-dipalladium (0) (0.092 g, 0.1 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.17 mg, 0.3 mmol) were dissolved in... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Tertiary halide.Tertiary halide.Primary amine | Secondary amine | c1ccc2c(c1)CN[NH]C2 | c1ccc2cnncc2c1 | c1cc[nH]n1.c1ccc2cnncc2c1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1.O | 130 | 8 | COCCN1NC(Br)(Br)c2ccccc2C1=O.Cc1cc(N)n(C(C)(C)C)n1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1.O>COCCn1nc(Nc2cc(C)nn2C(C)(C)C)c2ccccc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e033c88dbfea4a5d8f728e30e14989a2 | CC(C)c1ccc(NN)cc1.O=C1OC(=O)c2ccccc21>>CC(C)c1ccc(-n2nc(O)c3ccccc3c2=O)cc1 | Cl.C(C)(C)C1=CC=C(C=C1)NN.C1(C=2C(C(=O)O1)=CC=CC2)=O.O.C(=O)(O)[O-].[Na+]>>OC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)C(C)C | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][NH2:9])[cH:20][cH:21]1.O1[C:10](=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[C:18]1=[O:19]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7](-[n:8]2[n:9][c:10]([OH:11])[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[c:18]2=[O:19])[cH:20][cH:21]1 | CC(C)c1ccc(NN)cc1.O=C1OC(=O)c2ccccc21 | CC(C)c1ccc(-n2nc(O)c3ccccc3c2=O)cc1 | null | null | CC(=O)O | Miscellaneous | OtherReaction | 9ae05b8715b058eab04472a8d75553eb4ad446410693242c0b35af4fa9ebefd3 | c8f313725c64bf22e7bd79c82fb470d90d377272c01f895687191b28d98cf84d | O=c1c2ccccc2cnn1-c1ccccc1 | [NH2;D1;+0:1]-[NH;D2;+0:2]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[O;D1;H0:8]=[C;H0;D3;+0:9]1-O-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[c:12](:[c:13]):[c:14]-1:[c:15]>>[O;D1;H0:8]=[c;H0;D3;+0:9]1:[c:14](:[c:15]):[c:12](:[c:13]):[c;H0;D3;+0:10](-[OH;D1;+0:11]):[n;H0;D2;+0:1]:[n;H0;D3;+0:2]:1-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c... | 45 | [{"value": 45.0, "product": "OC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.5, "product": "OC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 125 | CELSIUS | null | null | 4-Isopropyl phenyl hydrazine hydrochloride (2.77 g, 14.6 mmol) was added in one portion to a stirred mixture of phthalic anhydride (2.0 g, 13 mmol) in HOAc (25 ml) at RT. The reaction mixture was heated to 125° C. for 2 hours, and then allowed to cool to RT. The resultant suspension was poured into H2O (100 ml), NaHCO3... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Anhydride.Ester.Ester | Aromatic alcohol | c1ccc2c(c1)COC2 | c1ccc2cnncc2c1 | c1ccccc1.c1ccc2cnncc2c1 | HO- | CC(=O)O | 125 | null | CC(C)c1ccc(NN)cc1.O=C1OC(=O)c2ccccc21>CC(=O)O>CC(C)c1ccc(-n2nc(O)c3ccccc3c2=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9390d35bf1aa41e2a0d7f442265d59bb | CC(C)c1ccc(-n2nc(O)c3ccccc3c2=O)cc1.O=P(Br)(Br)Br>>CC(C)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 | OC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)C(C)C.P(=O)(Br)(Br)Br.C(C)(C)(C)C1=C(C(=CC(=C1)C)C(C)(C)C)O>>BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)C(C)C | O[c:10]1[n:9][n:8](-[c:7]2[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:21][cH:20]2)[c:18](=[O:19])[c:17]2[c:12]1[cH:13][cH:14][cH:15][cH:16]2.O=P(Br)(Br)[Br:11]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7](-[n:8]2[n:9][c:10]([Br:11])[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[c:18]2=[O:19])[cH:20][cH:21]1 | CC(C)c1ccc(-n2nc(O)c3ccccc3c2=O)cc1.O=P(Br)(Br)Br | CC(C)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 | null | null | O | Functional Group Interconversion | OtherReaction | 06c5838cdb57cabe2d6458f62c09d8912e652528a8ca5b88b541675b701fe6ee | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | O=c1c2ccccc2cnn1-c1ccccc1 | Br-P(-Br)(=O)-[Br;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[#7;a:4](-[c:5]):[c:6]:[c:7]:[c:8]:1:[c:9]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[#7;a:4](-[c:5]):[c:6]:[c:7]:[c:8]:1:[c:9] | 41 | [{"value": 41.0, "product": "BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.5, "product": "BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Hydroxy-2-(4-isopropylphenyl)-2H-phthalazin-1-one (0.10 g, 0.36 mmol), phosphorus oxybromide (0.41 g, 1.4 mmol) and 2,6-di-tert-butyl-4-methylphenol (0.02 g, 0.09 mmol) were stirred at 150° C. for 30 min. H2O (100 ml) was added after cooling to RT. Extraction with DCM, drying of the combined organic phases over Na2SO... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | c1ccccc1.c1ccc2cnncc2c1 | HBr | O | null | null | CC(C)c1ccc(-n2nc(O)c3ccccc3c2=O)cc1.O=P(Br)(Br)Br>O>CC(C)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee7415b662b947ce8d13fbb7bcd579e5 | NNc1ccc(I)cc1.O=C1OC(=O)c2ccccc21>>O=c1c2ccccc2c(O)nn1-c1ccc(I)cc1 | IC1=CC=C(C=C1)NN.C1(C=2C(C(=O)O1)=CC=CC2)=O.O>>OC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)I | [NH2:11][NH:12][c:13]1[cH:14][cH:15][c:16]([I:17])[cH:18][cH:19]1.O1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10]>>[O:1]=[c:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[c:9]([OH:10])[n:11][n:12]1-[c:13]1[cH:14][cH:15][c:16]([I:17])[cH:18][cH:19]1 | NNc1ccc(I)cc1.O=C1OC(=O)c2ccccc21 | O=c1c2ccccc2c(O)nn1-c1ccc(I)cc1 | null | null | CC(=O)O | Miscellaneous | OtherReaction | 9ae05b8715b058eab04472a8d75553eb4ad446410693242c0b35af4fa9ebefd3 | c8f313725c64bf22e7bd79c82fb470d90d377272c01f895687191b28d98cf84d | O=c1c2ccccc2cnn1-c1ccccc1 | [NH2;D1;+0:1]-[NH;D2;+0:2]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[O;D1;H0:8]=[C;H0;D3;+0:9]1-O-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[c:12](:[c:13]):[c:14]-1:[c:15]>>[O;D1;H0:8]=[c;H0;D3;+0:9]1:[c:14](:[c:15]):[c:12](:[c:13]):[c;H0;D3;+0:10](-[OH;D1;+0:11]):[n;H0;D2;+0:1]:[n;H0;D3;+0:2]:1-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c... | 8.3 | [{"value": 8.0, "product": "OC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8.3, "product": "OC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 125 | CELSIUS | null | null | 4-Iodo phenyl hydrazine (8.97 g, 36.4 mmol) was added in one portion to a stirred mixture of phthalic anhydride (5.0 g, 33 mmol) in HOAc (40 ml) at RT. The reaction mixture was heated to 125° C. for 2 hours, and then allowed to cool to RT. The suspension was poured into H2O (100 ml) and the resulting solid was removed ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Anhydride.Ester.Ester | Aromatic alcohol | c1ccc2c(c1)COC2 | c1ccc2cnncc2c1 | c1ccc2cnncc2c1.c1ccccc1 | HO- | CC(=O)O | 125 | null | NNc1ccc(I)cc1.O=C1OC(=O)c2ccccc21>CC(=O)O>O=c1c2ccccc2c(O)nn1-c1ccc(I)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8bfa275789854f889496a16312b8b1e6 | O=c1c2ccccc2c(O)nn1-c1ccc(I)cc1.OB(O)c1ccccc1>>O=c1c2ccccc2c(O)nn1-c1ccc(-c2ccccc2)cc1 | OC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)I.C1(=CC=CC=C1)B(O)O.[F-].[K+]>>C1(=CC=C(C=C1)N1C(C2=CC=CC=C2C(=N1)O)=O)C1=CC=CC=C1 | I[c:16]1[cH:15][cH:14][c:13](-[n:12]2[c:2](=[O:1])[c:3]3[cH:4][cH:5][cH:6][cH:7][c:8]3[c:9]([OH:10])[n:11]2)[cH:24][cH:23]1.OB(O)[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[O:1]=[c:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[c:9]([OH:10])[n:11][n:12]1-[c:13]1[cH:14][cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22... | O=c1c2ccccc2c(O)nn1-c1ccc(I)cc1.OB(O)c1ccccc1 | O=c1c2ccccc2c(O)nn1-c1ccc(-c2ccccc2)cc1 | null | [Pd] | CO | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=c1c2ccccc2cnn1-c1ccc(-c2ccccc2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 78 | [{"value": 78.0, "product": "C1(=CC=C(C=C1)N1C(C2=CC=CC=C2C(=N1)O)=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.2, "product": "C1(=CC=C(C=C1)N1C(C2=CC=CC=C2C(=N1)O)=O)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Hydroxy-2-(4-iodophenyl)-2H-phthalazin-1-one (0.1 g, 0.3 mmol), phenyl boronic acid (0.04 g, 3 mmol), palladium black (0.02 g, 0.2 mmol) and KF (0.1 g, 18 mmol) were dissolved in MeOH (2 ml) and heated at reflux for 7 h. Removal of supernatant palladium by filtration, extraction with H2O and subsequent filtration of ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccc2cnncc2c1.c1ccccc1.c1ccccc1 | HI.B | [Pd].CO | null | null | O=c1c2ccccc2c(O)nn1-c1ccc(I)cc1.OB(O)c1ccccc1>[Pd].CO>O=c1c2ccccc2c(O)nn1-c1ccc(-c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ae98676653240b38ea79251b2ab7638 | Cc1cc(N)nn1C(C)(C)C.Cc1ccccc1-c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1>>Cc1ccccc1-c1ccc(-n2nc(Nc3cc(C)n(C(C)(C)C)n3)c3ccccc3c2=O)cc1 | BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C.C(C)(C)(C)N1N=C(C=C1C)N>>C(C)(C)(C)N1N=C(C=C1C)NC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C | [NH2:15][c:16]1[cH:17][c:18]([CH3:19])[n:20]([C:21]([CH3:22])([CH3:23])[CH3:24])[n:25]1.Br[c:14]1[n:13][n:12](-[c:11]2[cH:10][cH:9][c:8](-[c:7]3[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]3)[cH:35][cH:34]2)[c:32](=[O:33])[c:31]2[c:26]1[cH:27][cH:28][cH:29][cH:30]2>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[cH:9][cH:... | Cc1cc(N)nn1C(C)(C)C.Cc1ccccc1-c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 | Cc1ccccc1-c1ccc(-n2nc(Nc3cc(C)n(C(C)(C)C)n3)c3ccccc3c2=O)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | df3bfedad2a7f0f256464ab6dcf71ec93640ec0ccd579b3524f93860b3777b00 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1c2ccccc2c(Nc2cc[nH]n2)nn1-c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3](-[c:4]):[c:5]:[c:6]:[c:7]:1:[c:8].[C:9]-[#7;a:10]1:[#7;a:11]:[c:12](-[NH2;D1;+0:13]):[c:14]:[c:15]:1>>[C:9]-[#7;a:10]1:[#7;a:11]:[c:12](-[NH;D2;+0:13]-[c;H0;D3;+0:1]2:[#7;a:2]:[#7;a:3](-[c:4]):[c:5]:[c:6]:[c:7]:2:[c:8]):[c:14]:[c:15]:1 | 31 | [{"value": 31.0, "product": "C(C)(C)(C)N1N=C(C=C1C)NC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Bromo-2-(2′-methyl-biphenyl-4-yl)-2H-phtalazin-1-one (prepared from the appropriate starting materials in analogy to Method Q-1) was coupled with 1-tert-butyl-5-methyl-1H-pyrazol-3-ylamine in a Buchwald reaction as described in Method O to give the title compound (0.049 g, 31% yield). 1H-NMR: (400 MHz, D6-DMSO) 8.44 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | c1ccccc1.c1ccccc1.c1cc[nH]n1.c1ccc2cnncc2c1 | HBr | null | null | null | Cc1cc(N)nn1C(C)(C)C.Cc1ccccc1-c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1>>Cc1ccccc1-c1ccc(-n2nc(Nc3cc(C)n(C(C)(C)C)n3)c3ccccc3c2=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c29b0c5d146943498ead1a1135d007a0 | Cc1ccccc1-c1ccc(-n2nc(Nc3cc(C)n(C(C)(C)C)n3)c3ccccc3c2=O)cc1>>Cc1cc(Nc2nn(-c3ccc(-c4ccccc4C)cc3)c(=O)c3ccccc23)n[nH]1 | C(C)(C)(C)N1N=C(C=C1C)NC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C>>CC1=C(C=CC=C1)C1=CC=C(C=C1)N1C(C2=CC=CC=C2C(=N1)NC1=NNC(=C1)C)=O | CC(C)(C)[n:31]1[c:2]([CH3:1])[cH:3][c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11][c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[CH3:19])[cH:20][cH:21]3)[c:22](=[O:23])[c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]23)[n:30]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11][c:12](-[c:13]4[cH:14][... | Cc1ccccc1-c1ccc(-n2nc(Nc3cc(C)n(C(C)(C)C)n3)c3ccccc3c2=O)cc1 | Cc1cc(Nc2nn(-c3ccc(-c4ccccc4C)cc3)c(=O)c3ccccc23)n[nH]1 | null | null | C(=O)O | Deprotection | OtherReaction | a0192af0b7511f6d6cc432f36bd9f28eece2b654e788b7bbcaff6ec5f5442d28 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=c1c2ccccc2c(Nc2cc[nH]n2)nn1-c1ccc(-c2ccccc2)cc1 | C-C(-C)(-C)-[n;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1-[C;D1;H3:6]>>[C;D1;H3:6]-[c:5]1:[c:4]:[c:3]:[#7;a:2]:[nH;D2;+0:1]:1 | 83 | [{"value": 83.0, "product": "CC1=C(C=CC=C1)C1=CC=C(C=C1)N1C(C2=CC=CC=C2C(=N1)NC1=NNC(=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-(1-tert-Butyl-5-methyl-1H-pyrazol-3-ylamino)-2-(2′-methyl-biphenyl-4-yl)-2H-phtalazin-1-one was deprotected with formic acid as described in Method O to give the title compound (0.036 g, 83% yield). 1H-NMR: (400 MHz, D6-DMSO) 9.29 (1H, s), 8.52 (1H, d), 8.40 (1H, d), 8.17 (1H, s), 7.97 (1H, t), 7.93 (1H, t), 7.82 (2H... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc[nH]n1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccc2cnncc2c1 | Other | C(=O)O | null | null | Cc1ccccc1-c1ccc(-n2nc(Nc3cc(C)n(C(C)(C)C)n3)c3ccccc3c2=O)cc1>C(=O)O>Cc1cc(Nc2nn(-c3ccc(-c4ccccc4C)cc3)c(=O)c3ccccc23)n[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3dca0241a5eb440cb1fe3dd8e9e3268d | CN.O=C(O)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1>>CNC(=O)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 | BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C(=O)O)C=C1.C(=O)(N1C=NC=C1)N1C=NC=C1.CN>>BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C(=O)NC)C=C1 | [CH3:1][NH2:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[n:9]2[n:10][c:11]([Br:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[c:19]2=[O:20])[cH:21][cH:22]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[n:9]2[n:10][c:11]([Br:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[c:19]2=[O:20])[cH:21][cH:22]1 | CN.O=C(O)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 | CNC(=O)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 | null | null | CN(C)C=O.C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=c1c2ccccc2cnn1-c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[NH2;D1;+0:7]>>[C;D1;H3:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 77.9 | [{"value": 77.0, "product": "BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C(=O)NC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.9, "product": "BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C(=O)NC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 4-(4-Bromo-1-oxo-1H-phthalazin-2-yl)benzoic acid (0.15 g, 0.43 mmol) and 1,1′-carbonyldiimidazol (0.10 g, 0.65 mmol) were dissolved in DMF (10 ml) at RT. Methyl amine (0.33 ml of a 2M solution in THF, 0.65 mmol) were added and stirring was continued for 4 h. Evaporation of the solvent under reduced pressure, dilution w... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2cnncc2c1 | HO- | CN(C)C=O.C1CCOC1 | null | 4 | CN.O=C(O)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1>CN(C)C=O.C1CCOC1>CNC(=O)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b07406afbca042008efd59721c0618fa | CC(=O)Cl.Cc1cc(Nc2nn(-c3ccc(N)cc3)c(=O)c3ccccc23)n[nH]1>>CC(=O)Nc1ccc(-n2nc(Nc3cc(C)[nH]n3)c3ccccc3c2=O)cc1 | NC1=CC=C(C=C1)N1C(C2=CC=CC=C2C(=N1)NC1=NNC(=C1)C)=O.C(C)(=O)Cl>>CC1=CC(=NN1)NC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)NC(C)=O | Cl[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8](-[n:9]2[n:10][c:11]([NH:12][c:13]3[cH:14][c:15]([CH3:16])[nH:17][n:18]3)[c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]3[c:25]2=[O:26])[cH:27][cH:28]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8](-[n:9]2[n:10][c:11]([NH:12][c:13]3[cH:14][c:15]([CH3:16])[nH:17][n:18]... | CC(=O)Cl.Cc1cc(Nc2nn(-c3ccc(N)cc3)c(=O)c3ccccc23)n[nH]1 | CC(=O)Nc1ccc(-n2nc(Nc3cc(C)[nH]n3)c3ccccc3c2=O)cc1 | null | null | N1=CC=CC=C1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=c1c2ccccc2c(Nc2cc[nH]n2)nn1-c1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 30 | MINUTE | 2-(4-Amino-phenyl)-4-(5-methyl-1H-pyrazol-3-ylamino)-2H-phthalazin-1-one (C-2, 0.050 g, 0.15 mmol) was dissolved in pyridine (1 ml) at 0° C. Acetylchloride (0.024 ml, 0.33 mmol) was added and stirring was continued for 30 min at 0° C. before the mixture was allowed to warm to RT. The solvent was evaporated after 2 h st... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1cn[nH]c1.c1ccc2cnncc2c1 | HCl | N1=CC=CC=C1 | null | 0.5 | CC(=O)Cl.Cc1cc(Nc2nn(-c3ccc(N)cc3)c(=O)c3ccccc23)n[nH]1>N1=CC=CC=C1>CC(=O)Nc1ccc(-n2nc(Nc3cc(C)[nH]n3)c3ccccc3c2=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d7718a6e8fd4fbc9bbe76373cfb88cd | Cc1cc(Nc2nn(-c3ccc(Cl)cc3)c(=O)c3ccccc23)n[nH]1.Nc1ccccc1>>Cc1cc(Nc2nn(-c3ccc(Nc4ccccc4)cc3)c(=O)c3ccccc23)n[nH]1 | ClC1=CC=C(C=C1)N1C(C2=CC=CC=C2C(=N1)NC1=NNC(=C1)C)=O.NC1=CC=CC=C1.CC(C)(C)[O-].[Na+].C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C>>CC1=CC(=NN1)NC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)NC1=CC=CC=C1 | Cl[c:12]1[cH:11][cH:10][c:9](-[n:8]2[n:7][c:6]([NH:5][c:4]3[cH:3][c:2]([CH3:1])[nH:31][n:30]3)[c:29]3[c:24]([c:22]2=[O:23])[cH:25][cH:26][cH:27][cH:28]3)[cH:21][cH:20]1.[NH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11][c:12]([NH:13][c:14]4[cH:15][... | Cc1cc(Nc2nn(-c3ccc(Cl)cc3)c(=O)c3ccccc23)n[nH]1.Nc1ccccc1 | Cc1cc(Nc2nn(-c3ccc(Nc4ccccc4)cc3)c(=O)c3ccccc23)n[nH]1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1c2ccccc2c(Nc2cc[nH]n2)nn1-c1ccc(Nc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:4]:[c:5] | 2 | [{"value": 2.0, "product": "CC1=CC(=NN1)NC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)NC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 1.7, "product": "CC1=CC(=NN1)NC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)NC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(4-Chloro-phenyl)-4-(5-methyl-1H-pyrazol-3-ylamino)-2H-phthalazin-1-one (B-1, 0.10 g, 0.28 mmol), aniline (0.034 g, 0.37 mmol), NaOtBu (0.041 g, 0.43 mmol), tris-(dibenzylideneacetone)-dipalladium (0.026 g, 0.028 mmol) and 2-(di-t-butylphosphino)-biphenyl (0.017 g, 0.057 mmol) under argon were heated to 100° C. for 1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1cn[nH]c1.c1ccccc1.c1ccccc1.c1ccc2cnncc2c1 | HCl | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | null | null | Cc1cc(Nc2nn(-c3ccc(Cl)cc3)c(=O)c3ccccc23)n[nH]1.Nc1ccccc1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]>Cc1cc(Nc2nn(-c3ccc(Nc4ccccc4)cc3)c(=O)c3ccccc23)n[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-936b886980574373bfd547f0b63a6006 | Cc1cc(N)n(C(C)(C)C)n1.O=c1c2ccccc2c(Br)nn1-c1ccc(Cl)cc1>>Cc1cc(Nc2nn(-c3ccc(Cl)cc3)c(=O)c3ccccc23)n(C(C)(C)C)n1 | BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)Cl.C(C)(C)(C)N1N=C(C=C1N)C.C([O-])([O-])=O.[Cs+].[Cs+].C1(=CC=CC=C1)P(C1=CC=CC=2C(C3=CC=CC(=C3OC12)P(C1=CC=CC=C1)C1=CC=CC=C1)(C)C)C1=CC=CC=C1>>C(C)(C)(C)N1N=C(C=C1NC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)Cl)C | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:24]([C:25]([CH3:26])([CH3:27])[CH3:28])[n:29]1.Br[c:6]1[n:7][n:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]2)[c:16](=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]3)[c:16]... | Cc1cc(N)n(C(C)(C)C)n1.O=c1c2ccccc2c(Br)nn1-c1ccc(Cl)cc1 | Cc1cc(Nc2nn(-c3ccc(Cl)cc3)c(=O)c3ccccc23)n(C(C)(C)C)n1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | df3bfedad2a7f0f256464ab6dcf71ec93640ec0ccd579b3524f93860b3777b00 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1c2ccccc2c(Nc2ccn[nH]2)nn1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3](-[c:4]):[c:5]:[c:6]:[c:7]:1:[c:8].[C:9]-[#7;a:10]1:[#7;a:11]:[c:12]:[c:13]:[c:14]:1-[NH2;D1;+0:15]>>[C:9]-[#7;a:10]1:[#7;a:11]:[c:12]:[c:13]:[c:14]:1-[NH;D2;+0:15]-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3](-[c:4]):[c:5]:[c:6]:[c:7]:1:[c:8] | null | [] | null | null | null | null | 200 mg 4-Bromo-2-(4-chloro-phenyl)-2H-phthalazin-1-one (prepared as described in Method R), 91 mg 1-tert.-butyl-3-methyl-1H-pyrazol-5-ylamine, 310 mg cesium carbonate, 21 mg 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene and 16.4 mg tris-(di-benzylideneacetone)-dipalladium in 2 ml dry dioxane were stirred under nitrog... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | c1cc[nH]n1.c1ccccc1.c1ccc2cnncc2c1 | HBr | O1CCOCC1 | null | null | Cc1cc(N)n(C(C)(C)C)n1.O=c1c2ccccc2c(Br)nn1-c1ccc(Cl)cc1>O1CCOCC1>Cc1cc(Nc2nn(-c3ccc(Cl)cc3)c(=O)c3ccccc23)n(C(C)(C)C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7a1b197c94924105a72dc888b7eebf3f | C1CCNCC1.Cc1cc(Nc2nn(-c3ccc(Cl)cc3)c(=O)c3ccccc23)n(C(C)(C)C)n1>>Cc1cc(Nc2nn(-c3ccc(N4CCCCC4)cc3)c(=O)c3ccccc23)n(C(C)(C)C)n1 | C(C)(C)(C)N1N=C(C=C1NC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)Cl)C.N1CCCCC1.CC(C)(C)[O-].[Na+].C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C>>C(C)(C)(C)N1N=C(C=C1NC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)N1CCCCC1)C | [NH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1.Cl[c:12]1[cH:11][cH:10][c:9](-[n:8]2[n:7][c:6]([NH:5][c:4]3[cH:3][c:2]([CH3:1])[n:34][n:29]3[C:30]([CH3:31])([CH3:32])[CH3:33])[c:28]3[c:23]([c:21]2=[O:22])[cH:24][cH:25][cH:26][cH:27]3)[cH:20][cH:19]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:1... | C1CCNCC1.Cc1cc(Nc2nn(-c3ccc(Cl)cc3)c(=O)c3ccccc23)n(C(C)(C)C)n1 | Cc1cc(Nc2nn(-c3ccc(N4CCCCC4)cc3)c(=O)c3ccccc23)n(C(C)(C)C)n1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=c1c2ccccc2c(Nc2ccn[nH]2)nn1-c1ccc(N2CCCCC2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | 13 | [{"value": 13.0, "product": "C(C)(C)(C)N1N=C(C=C1NC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)N1CCCCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.3, "product": "C(C)(C)(C)N1N=C(C=C1NC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)N1CCCCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-(2-tert-Butyl-5-methyl-2H-pyrazol-3-ylamino)-2-(4-chlorophenyl)-2H-phthalazin-1-one (0.10 g, 0.25 mmol), piperidine (0.025 g, 0.29 mmol), NaOtBu (0.033 g, 0.34 mmol), tris-(dibenzylideneacetone)-dipalladium (0.06 g, 0.008 mmol) and 2-(di-t-butylphosphino)-biphenyl (0.004 g, 0.014 mmol) under argon were heated to 100°... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1 | c1cc[nH]n1.c1ccccc1.C1CC[NH]CC1.c1ccc2cnncc2c1 | HCl | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | null | null | C1CCNCC1.Cc1cc(Nc2nn(-c3ccc(Cl)cc3)c(=O)c3ccccc23)n(C(C)(C)C)n1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]>Cc1cc(Nc2nn(-c3ccc(N4CCCCC4)cc3)c(=O)c3ccccc23)n(C(C)(C)C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c11b2e091a434ce3a5ac087e934763d8 | Cc1cc(Nc2nn(-c3ccc(N4CCCCC4)cc3)c(=O)c3ccccc23)n(C(C)(C)C)n1>>Cc1cc(Nc2nn(-c3ccc(N4CCCCC4)cc3)c(=O)c3ccccc23)[nH]n1 | C(C)(C)(C)N1N=C(C=C1NC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)N1CCCCC1)C>>CC=1C=C(NN1)NC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)N1CCCCC1 | CC(C)(C)[n:29]1[c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11][c:12]([N:13]4[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]4)[cH:19][cH:20]3)[c:21](=[O:22])[c:23]3[cH:24][cH:25][cH:26][cH:27][c:28]23)[cH:3][c:2]([CH3:1])[n:30]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11][c:12]([N:13]4[CH2:14][CH2... | Cc1cc(Nc2nn(-c3ccc(N4CCCCC4)cc3)c(=O)c3ccccc23)n(C(C)(C)C)n1 | Cc1cc(Nc2nn(-c3ccc(N4CCCCC4)cc3)c(=O)c3ccccc23)[nH]n1 | null | null | C(=O)O.C(Cl)Cl | Deprotection | OtherReaction | a0192af0b7511f6d6cc432f36bd9f28eece2b654e788b7bbcaff6ec5f5442d28 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=c1c2ccccc2c(Nc2ccn[nH]2)nn1-c1ccc(N2CCCCC2)cc1 | C-C(-C)(-C)-[n;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1-[#7:6]>>[#7:6]-[c:5]1:[c:4]:[c:3]:[#7;a:2]:[nH;D2;+0:1]:1 | 57.6 | [{"value": 57.0, "product": "CC=1C=C(NN1)NC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)N1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.6, "product": "CC=1C=C(NN1)NC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)N1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | null | null | 4-(2-tert-Butyl-5-methyl-2H-pyrazol-3-ylamino)-2-(4-piperidin-1-yl-phenyl)-2H-phthalazin-1-one (0.012 g, 0.026 mmol) was dissolved in formic acid (1 ml) and heated at 95° C. for 4 h. The resulting raw product was dissolved in DCM, after evaporation of formic acid. Extraction with a saturated aqueous NaHCO3 solution, co... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc[nH]n1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.C1CC[NH]CC1.c1ccc2cnncc2c1 | Other | C(=O)O.C(Cl)Cl | 95 | null | Cc1cc(Nc2nn(-c3ccc(N4CCCCC4)cc3)c(=O)c3ccccc23)n(C(C)(C)C)n1>C(=O)O.C(Cl)Cl>Cc1cc(Nc2nn(-c3ccc(N4CCCCC4)cc3)c(=O)c3ccccc23)[nH]n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f71da353e1b5486fb7a994ac7a0fd029 | O=C1c2ccccc2C(=O)N1Nc1ccc(C(F)(F)F)cc1Cl>>O=c1[nH]n(-c2ccc(C(F)(F)F)cc2Cl)c(=O)c2ccccc12 | ClC1=C(C=CC(=C1)C(F)(F)F)NN1C(C2=CC=CC=C2C1=O)=O.ClC1=C(C=CC(=C1)C(F)(F)F)NN.[O-]CC.[Na+]>>ClC1=C(C=CC(=C1)C(F)(F)F)N1C(C2=CC=CC=C2C(N1)=O)=O | [O:1]=[C:2]1[N:3]([NH:4][c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]2[Cl:15])[C:16](=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]21>>[O:1]=[c:2]1[nH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]2[Cl:15])[c:16](=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12 | O=C1c2ccccc2C(=O)N1Nc1ccc(C(F)(F)F)cc1Cl | O=c1[nH]n(-c2ccc(C(F)(F)F)cc2Cl)c(=O)c2ccccc12 | null | null | CCO | Miscellaneous | OtherReaction | ed4e204457633c1559dd5376cb21dd5f2d8d95e71434bfc03e4b7b4a4ea68ba1 | 79b55640d2b701f8e538df71aa6805426e01a491c275f98bc763986302a740ca | O=c1[nH]n(-c2ccccc2)c(=O)c2ccccc12 | [Cl;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[NH;D2;+0:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:9](:[c:10]):[c:11](:[c:12])-[C;H0;D3;+0:13]-1=[O;D1;H0:14]):[c:15]:[c:16]>>[Cl;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[n;H0;D3;+0:5]1:[nH;D2;+0:6]:[c;H0;D3;+0:13](=[O;D1;H0:14]):[c:11](:[c:12]):[c:9](:[c:10]):[c;H0;D... | null | [] | 85 | CELSIUS | 2 | HOUR | 1.74 g 2-(2-Chloro-4-trifluoromethyl-phenylamino)-isoindole-1,3-dione (prepared from 2-chloro-4-trifluoromethyl-phenylhydrazine analogously to method A) in 80 ml dry EtOH were treated with 347 mg sodium ethoxide and the mixture was stirred at 85° C. for 2 hrs. After cooling, the mixture was evaporated and dissolved in ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | c1ccc2c(c1)C[NH]C2 | c1nncc2ccccc12 | c1ccccc1.c1nncc2ccccc12 | null | CCO | 85 | 2 | O=C1c2ccccc2C(=O)N1Nc1ccc(C(F)(F)F)cc1Cl>CCO>O=c1[nH]n(-c2ccc(C(F)(F)F)cc2Cl)c(=O)c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-31dcd2062b3b4bc9b735d00e5825c3f3 | O=c1c2ccccc2c(Br)nn1-c1ccc([N+](=O)[O-])cc1>>Nc1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 | BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)[N+](=O)[O-]>>NC1=CC=C(C=C1)N1C(C2=CC=CC=C2C(=N1)Br)=O | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5](-[n:6]2[n:7][c:8]([Br:9])[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[c:16]2=[O:17])[cH:18][cH:19]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[n:6]2[n:7][c:8]([Br:9])[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[c:16]2=[O:17])[cH:18][cH:19]1 | O=c1c2ccccc2c(Br)nn1-c1ccc([N+](=O)[O-])cc1 | Nc1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 | null | O=[Pt]=O | CCOC(=O)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1c2ccccc2cnn1-c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 67 | [{"value": 67.0, "product": "NC1=CC=C(C=C1)N1C(C2=CC=CC=C2C(=N1)Br)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.5, "product": "NC1=CC=C(C=C1)N1C(C2=CC=CC=C2C(=N1)Br)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 4-Bromo-2-(4-nitro-phenyl)-2H-phthalazin-1-one (see Method B) (1.0 g, 2.9 mmol) and PtO2 (0.13 g, 0.58 mmol) were dissolved in EtOAc (40 ml) at RT. The mixture was hydrogenated at ambient pressure for 2 h, before the catalyst was filtered off to yield title compound (0.61 g, 67% yield). 1H-NMR: (400 MHz, D6-DMSO) 8.34 ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2cnncc2c1 | Other | O=[Pt]=O.CCOC(=O)C | null | 2 | O=c1c2ccccc2c(Br)nn1-c1ccc([N+](=O)[O-])cc1>O=[Pt]=O.CCOC(=O)C>Nc1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-78c2137e25964d63bff8a2c9337b58ec | CC(=O)Nc1ccc(-n2nc(Br)c3ccccc3c2=O)cc1.CCI>>CCN(C(C)=O)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 | [H-].[Na+].BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)NC(C)=O.C(C)I>>BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)N(C(C)=O)CC | [NH:3]([C:4]([CH3:5])=[O:6])[c:7]1[cH:8][cH:9][c:10](-[n:11]2[n:12][c:13]([Br:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[c:21]2=[O:22])[cH:23][cH:24]1.I[CH2:2][CH3:1]>>[CH3:1][CH2:2][N:3]([C:4]([CH3:5])=[O:6])[c:7]1[cH:8][cH:9][c:10](-[n:11]2[n:12][c:13]([Br:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[c:21]2=[O:... | CC(=O)Nc1ccc(-n2nc(Br)c3ccccc3c2=O)cc1.CCI | CCN(C(C)=O)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | db9b1b8804b469c037e0a5ba95031d33e73dcd5fc2a6fa79163c623adf75f2a1 | 4a6c1e88c9e8bed487b746792f88d478ff36cc235f9a217d4632e6babdebdc9a | O=c1c2ccccc2cnn1-c1ccccc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[C;D1;H3:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:4](-[C;D1;H3:3])=[O;D1;H0:5])-[c:7](:[c:8]):[c:9] | 14 | [{"value": 14.0, "product": "BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)N(C(C)=O)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.9, "product": "BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)N(C(C)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | NaH (95%, 0.005 g, 0.21 mmol) was added slowly at RT to a solution of N-[4-(4-Bromo-1-oxo-1H-phthalazin-2-yl)-phenyl]acetamide (0.070 g, 0.20 mmol) in DMF (2 ml). Stirring was continued for 1 h before ethyl iodide (0.046 g, 0.29 mmol) was added. Stirring was continued for 12 h before the solvent was evaporated in vacuu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amide | Tertiary amide | null | null | c1ccccc1.c1ccc2cnncc2c1 | HI | CN(C)C=O | null | 12 | CC(=O)Nc1ccc(-n2nc(Br)c3ccccc3c2=O)cc1.CCI>CN(C)C=O>CCN(C(C)=O)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-893af672312646d793f180c0be289a75 | CCN(C(C)=O)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1.Cc1cc(N)nn1C(=O)OC(C)(C)C>>CCN(C(C)=O)c1ccc(-n2nc(Nc3cc(C)[nH]n3)c3ccccc3c2=O)cc1 | BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)N(C(C)=O)CC.C(C)(C)(C)OC(=O)N1N=C(C=C1C)N.C(=O)([O-])[O-].[Cs+].[Cs+].C1(=CC=CC=C1)P(C1=CC=CC=2C(C3=CC=CC(=C3OC12)P(C1=CC=CC=C1)C1=CC=CC=C1)(C)C)C1=CC=CC=C1>>C(C)N(C(C)=O)C1=CC=C(C=C1)N1C(C2=CC=CC=C2C(=N1)NC1=NNC(=C1)C)=O | Br[c:13]1[n:12][n:11](-[c:10]2[cH:9][cH:8][c:7]([N:3]([CH2:2][CH3:1])[C:4]([CH3:5])=[O:6])[cH:30][cH:29]2)[c:27](=[O:28])[c:26]2[c:21]1[cH:22][cH:23][cH:24][cH:25]2.CC(C)(C)OC(=O)[n:19]1[c:17]([CH3:18])[cH:16][c:15]([NH2:14])[n:20]1>>[CH3:1][CH2:2][N:3]([C:4]([CH3:5])=[O:6])[c:7]1[cH:8][cH:9][c:10](-[n:11]2[n:12][c:13]... | CCN(C(C)=O)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1.Cc1cc(N)nn1C(=O)OC(C)(C)C | CCN(C(C)=O)c1ccc(-n2nc(Nc3cc(C)[nH]n3)c3ccccc3c2=O)cc1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O | Heteroatom Alkylation and Arylation | OtherReaction | 727ec3a8ea2865973489639a32cf9e801f58db4c2ed20bdae1177d9ca76b4901 | 714b1e79c619852a8cc4d3efd820398d7a36b06618a87a6b24e58724f087eb50 | O=c1c2ccccc2c(Nc2cc[nH]n2)nn1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3](-[c:4]):[c:5]:[c:6]:[c:7]:1:[c:8].C-C(-C)(-C)-O-C(=O)-[n;H0;D3;+0:9]1:[#7;a:10]:[c:11](-[NH2;D1;+0:12]):[c:13]:[c:14]:1-[C;D1;H3:15]>>[C;D1;H3:15]-[c:14]1:[c:13]:[c:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1]2:[#7;a:2]:[#7;a:3](-[c:4]):[c:5]:[c:6]:[c:7]:2:[c:8]):[#7;a:10]:[nH;D2;+0:9]:1 | 27.6 | [{"value": 23.0, "product": "C(C)N(C(C)=O)C1=CC=C(C=C1)N1C(C2=CC=CC=C2C(=N1)NC1=NNC(=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.6, "product": "C(C)N(C(C)=O)C1=CC=C(C=C1)N1C(C2=CC=CC=C2C(=N1)NC1=NNC(=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-[4-(4-Bromo-1-oxo-1H-phthalazin-2-yl)-phenyl]-N-ethyl-acetamide (0.10 g, 0.027 mmol), 3-amino-5-methyl-pyrazole-1-carboxylic acid tert-butyl ester (0.006 g, 0.03 mmol), Cs2CO3 (0.01 g, 0.03 mmol), tris-(dibenzylideneacetone)-dipalladium (0.001 g, 0.001 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.002 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Primary amine.Boc | Secondary amine | c1ccc2cnncc2c1.c1cc[nH]n1 | c1cn[nH]c1.c1ccc2cnncc2c1 | c1ccccc1.c1cn[nH]c1.c1ccc2cnncc2c1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O | null | null | CCN(C(C)=O)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1.Cc1cc(N)nn1C(=O)OC(C)(C)C>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O>CCN(C(C)=O)c1ccc(-n2nc(Nc3cc(C)[nH]n3)c3ccccc3c2=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d0de79d32f94b1bac46ec1d0be142ad | CC(C)(C)[S-].O=c1c2ccccc2c(O)nn1-c1ccc(I)cc1>>CC(C)(C)Sc1ccc(-n2[nH]c(=O)c3ccccc3c2=O)cc1 | OC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)I.CC(C)(C)[S-].[Na+].C(CO)O.O>>C(C)(C)(C)SC1=CC=C(C=C1)N1C(C2=CC=CC=C2C(N1)=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[S-:5].I[c:6]1[cH:7][cH:8][c:9](-[n:10]2[n:11][c:12]([OH:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[c:20]2=[O:21])[cH:22][cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[S:5][c:6]1[cH:7][cH:8][c:9](-[n:10]2[nH:11][c:12](=[O:13])[c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[c:20]2=[O:21])[cH:22][c... | CC(C)(C)[S-].O=c1c2ccccc2c(O)nn1-c1ccc(I)cc1 | CC(C)(C)Sc1ccc(-n2[nH]c(=O)c3ccccc3c2=O)cc1 | null | [Cu]I | CN1C(CCC1)=O | Acylation | OtherReaction | 64cbb09a5ab577405ea5cfa10dfce42e76a2e0a7528168625741c34dd9e54b08 | 1c939e95dddf9213d9a60c74d697ca42a18d84a531614de813ecf769aefb5fdc | O=c1[nH]n(-c2ccccc2)c(=O)c2ccccc12 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[#7;a:5]2:[c:6]:[c:7]:[c:8](:[c:9]):[c;H0;D3;+0:10](-[OH;D1;+0:11]):[n;H0;D2;+0:12]:2):[c:13]:[c:14]:1.[C;D1;H3:15]-[C:16](-[C;D1;H3:17])(-[C;D1;H3:18])-[S-;H0;D1:19]>>[C;D1;H3:15]-[C:16](-[C;D1;H3:17])(-[C;D1;H3:18])-[S;H0;D2;+0:19]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[#7;a:5]2:[c:6... | null | [] | 150 | CELSIUS | 4 | DAY | 4-Hydroxy-2-(4-iodo-phenyl)-2H-phthalazin-1-one (see Method Q) (0.30 g, 0.8 mmol), sodium 2-methyl-propane-2-thiolate (0.094 g, 0.8 mmol), CuI (0.011 g, 0.06 mmol) and ethylene glycol (0.10 g, 1.6 mmol) were dissolved in N-methyl-pyrrolidinone (NMP) (0.5 ml) under argon and heated to 150° C. Stirring at this temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Monosulfide | c1ccccc1.c1ccc2cnncc2c1 | c1ccccc1.c1nncc2ccccc12 | c1ccccc1.c1nncc2ccccc12 | I- | [Cu]I.CN1C(CCC1)=O | 150 | 96 | CC(C)(C)[S-].O=c1c2ccccc2c(O)nn1-c1ccc(I)cc1>[Cu]I.CN1C(CCC1)=O>CC(C)(C)Sc1ccc(-n2[nH]c(=O)c3ccccc3c2=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-56bb6c0eb99b40758d12cfcc7d6b1c8b | CC(C)(C)S(=O)(=O)c1ccc(-n2[nH]c(=O)c3ccccc3c2=O)cc1.O=P(Br)(Br)Br>>CC(C)(C)S(=O)(=O)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 | CC(C)(C)S(=O)(=O)C1=CC=C(C=C1)N1C(C2=CC=CC=C2C(N1)=O)=O.P(=O)(Br)(Br)Br>>BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)S(=O)(=O)C(C)(C)C | O=[c:14]1[nH:13][n:12](-[c:11]2[cH:10][cH:9][c:8]([S:5]([C:2]([CH3:1])([CH3:3])[CH3:4])(=[O:6])=[O:7])[cH:25][cH:24]2)[c:22](=[O:23])[c:21]2[c:16]1[cH:17][cH:18][cH:19][cH:20]2.O=P(Br)(Br)[Br:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][c:11](-[n:12]2[n:13][c:14]([Br:15])[c:16]3[cH:17][cH... | CC(C)(C)S(=O)(=O)c1ccc(-n2[nH]c(=O)c3ccccc3c2=O)cc1.O=P(Br)(Br)Br | CC(C)(C)S(=O)(=O)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 | null | null | O | Functional Group Interconversion | OtherReaction | aec09823bf3fa9f4c0e2e35cd267307e3a1028afc5e7158b1c38e567a1405867 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=c1c2ccccc2cnn1-c1ccccc1 | Br-P(-Br)(=O)-[Br;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[#7;a:4](-[c:5]):[c:6]:[c:7]:[c:8]:1:[c:9]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[#7;a:4](-[c:5]):[c:6]:[c:7]:[c:8]:1:[c:9] | 25.4 | [{"value": 18.0, "product": "BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)S(=O)(=O)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 25.4, "product": "BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)S(=O)(=O)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-[4-(2-methyl-propane-2-sulfonyl)-phenyl]-2,3-dihydro-phthalazine-1,4-dione (0.20 g, 0.56 mmol) and phosphorus oxybromide (0.48 g, 1.7 mmol) were stirred at 150° C. for 1 h. H2O (50 ml) was added after cooling to RT. Extraction with DCM, drying of the combined organic phases over Na2SO4, evaporation of the solvent and... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1nncc2ccccc12 | c1ccc2cnncc2c1 | c1ccccc1.c1ccc2cnncc2c1 | HBr | O | null | null | CC(C)(C)S(=O)(=O)c1ccc(-n2[nH]c(=O)c3ccccc3c2=O)cc1.O=P(Br)(Br)Br>O>CC(C)(C)S(=O)(=O)c1ccc(-n2nc(Br)c3ccccc3c2=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fd6aee5fbb5e4233b94f6c26b29e4c9b | O=c1c2ccccc2c(O)nn1-c1ccc(I)cc1.Sc1ccccc1>>O=c1[nH]n(-c2ccc(Sc3ccccc3)cc2)c(=O)c2ccccc12 | OC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)I.C1(=CC=CC=C1)S.C(CO)O.O>>C1(=CC=CC=C1)SC1=CC=C(C=C1)N1C(C2=CC=CC=C2C(N1)=O)=O | I[c:8]1[cH:7][cH:6][c:5](-[n:4]2[n:3][c:2]([OH:1])[c:25]3[c:20]([c:18]2=[O:19])[cH:21][cH:22][cH:23][cH:24]3)[cH:17][cH:16]1.[SH:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[O:1]=[c:2]1[nH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([S:9][c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[cH:16][cH:17]2)[c:18](=[O:19])[c:20]2[cH:21][... | O=c1c2ccccc2c(O)nn1-c1ccc(I)cc1.Sc1ccccc1 | O=c1[nH]n(-c2ccc(Sc3ccccc3)cc2)c(=O)c2ccccc12 | null | [Cu]I | CN1C(CCC1)=O | Acylation | OtherReaction | 162ff50b85787eaf701655a7c5919461c16944a48adea402e2852c1687067a36 | 0fb1e3adaecd548000a3596df93e4b03126b3acab79ba56f4aa02bab2c8f2538 | O=c1[nH]n(-c2ccc(Sc3ccccc3)cc2)c(=O)c2ccccc12 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[#7;a:5]2:[c:6]:[c:7]:[c:8](:[c:9]):[c;H0;D3;+0:10](-[OH;D1;+0:11]):[n;H0;D2;+0:12]:2):[c:13]:[c:14]:1.[SH;D1;+0:15]-[c:16](:[c:17]):[c:18]>>[O;H0;D1;+0:11]=[c;H0;D3;+0:10]1:[nH;D2;+0:12]:[#7;a:5](-[c:4]2:[c:3]:[c:2]:[c;H0;D3;+0:1](-[S;H0;D2;+0:15]-[c:16](:[c:17]):[c:18]):[c:14]:[c:... | null | [] | 90 | CELSIUS | 26 | HOUR | 4-Hydroxy-2-(4-iodo-phenyl)-2H-phthalazin-1-one (see Method Q) (0.20 g, 0.55 mmol), thiophenol (0.061 g, 0.55 mmol), CuI (0.006 g, 0.03 mmol) and ethylene glycol (0.070 g, 1.1 mmol) were dissolved in N-methyl-pyrrolidinone (NMP) (1 ml) under argon and heated to 90° C. Stirring at this temperature was continued for 26 h... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol.Aromatic thiol | Monosulfide | c1ccccc1.c1ccc2cnncc2c1 | c1ccccc1.c1nncc2ccccc12 | c1ccccc1.c1ccccc1.c1nncc2ccccc12 | HI | [Cu]I.CN1C(CCC1)=O | 90 | 26 | O=c1c2ccccc2c(O)nn1-c1ccc(I)cc1.Sc1ccccc1>[Cu]I.CN1C(CCC1)=O>O=c1[nH]n(-c2ccc(Sc3ccccc3)cc2)c(=O)c2ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1e4b347d862345669bba467f15ee28c6 | O=P(Br)(Br)Br.O=c1[nH]n(-c2ccc(Sc3ccccc3)cc2)c(=O)c2ccccc12>>O=c1c2ccccc2c(Br)nn1-c1ccc(Sc2ccccc2)cc1 | C1(=CC=CC=C1)SC1=CC=C(C=C1)N1C(C2=CC=CC=C2C(N1)=O)=O.P(=O)(Br)(Br)Br>>BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)SC1=CC=CC=C1 | O=P(Br)(Br)[Br:10].O=[c:9]1[c:8]2[c:3]([c:2](=[O:1])[n:12](-[c:13]3[cH:14][cH:15][c:16]([S:17][c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[cH:24][cH:25]3)[nH:11]1)[cH:4][cH:5][cH:6][cH:7]2>>[O:1]=[c:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[c:9]([Br:10])[n:11][n:12]1-[c:13]1[cH:14][cH:15][c:16]([S:17][c:18]2[cH:19][cH:20... | O=P(Br)(Br)Br.O=c1[nH]n(-c2ccc(Sc3ccccc3)cc2)c(=O)c2ccccc12 | O=c1c2ccccc2c(Br)nn1-c1ccc(Sc2ccccc2)cc1 | null | null | O | Functional Group Interconversion | OtherReaction | aec09823bf3fa9f4c0e2e35cd267307e3a1028afc5e7158b1c38e567a1405867 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=c1c2ccccc2cnn1-c1ccc(Sc2ccccc2)cc1 | Br-P(-Br)(=O)-[Br;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[#7;a:4](-[c:5]):[c:6]:[c:7]:[c:8]:1:[c:9]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[#7;a:4](-[c:5]):[c:6]:[c:7]:[c:8]:1:[c:9] | 86 | [{"value": 86.0, "product": "BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)SC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.2, "product": "BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)SC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(4-Phenylsulfanyl-phenyl)-2,3-dihydro-phthalazine-1,4-dione (0.10 g, 0.29 mmol) and phosphorus oxybromide (0.33 g, 12 mmol) were stirred at 150° C. for 40 min. H2O (50 ml) was added after cooling to RT. Extraction with DCM, drying of the combined organic phases over Na2SO4, evaporation of the solvent and purification... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1nncc2ccccc12 | c1ccc2cnncc2c1 | c1ccc2cnncc2c1.c1ccccc1.c1ccccc1 | HBr | O | null | null | O=P(Br)(Br)Br.O=c1[nH]n(-c2ccc(Sc3ccccc3)cc2)c(=O)c2ccccc12>O>O=c1c2ccccc2c(Br)nn1-c1ccc(Sc2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-82d629c958ce4a21bb12097c136b6ec0 | O=C(OO)c1cccc(Cl)c1.O=c1c2ccccc2c(Br)nn1-c1ccc(Sc2ccccc2)cc1>>O=c1c2ccccc2c(Br)nn1-c1ccc(S(=O)c2ccccc2)cc1 | BrC1=NN(C(C2=CC=CC=C12)=O)C1=CC=C(C=C1)SC1=CC=CC=C1.C1=CC(=CC(=C1)Cl)C(=O)OO>>C1(=CC=CC=C1)S(=O)C1=CC=C(C=C1)N1C(C2=CC=CC=C2C(=N1)Br)=O | O=C(O[OH:18])c1cccc(Cl)c1.[O:1]=[c:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[c:9]([Br:10])[n:11][n:12]1-[c:13]1[cH:14][cH:15][c:16]([S:17][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:25][cH:26]1>>[O:1]=[c:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[c:9]([Br:10])[n:11][n:12]1-[c:13]1[cH:14][cH:15][c:16]([S:17](=[O:18])[c:1... | O=C(OO)c1cccc(Cl)c1.O=c1c2ccccc2c(Br)nn1-c1ccc(Sc2ccccc2)cc1 | O=c1c2ccccc2c(Br)nn1-c1ccc(S(=O)c2ccccc2)cc1 | null | null | C(Cl)Cl | Oxidation | Sulfanyl to sulfinyl_peroxide | 95b5106b07a173d8eafc1c9c8a6c938befe131c3d1caaf5886529b7aee55ea9d | 7652b53bb02130dccfe4b1e8905d7f3db7f05ff3a95a0003c1bab09b1ad4083e | O=c1c2ccccc2cnn1-c1ccc(S(=O)c2ccccc2)cc1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[c:2]:[c:3](-[S;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8]>>[O;H0;D1;+0:1]=[S;H0;D3;+0:4](-[c:3](:[c:2]):[c:8])-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | 4-Bromo-2-(4-phenylsulfanyl-phenyl)-2H-phthalazin-1-one (0.095 g, 0.23 mmol) and MCPBA (0.052 g, 0.23 mmol) were stirred at RT in DCM (1 ml) for 1 h. The title compound was obtained after evaporation of the solvent in vacuum and subsequent purification of the raw product by chromatography over silica gel with heptane:D... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfoxide | c1ccccc1 | null | c1ccc2cnncc2c1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | null | O=C(OO)c1cccc(Cl)c1.O=c1c2ccccc2c(Br)nn1-c1ccc(Sc2ccccc2)cc1>C(Cl)Cl>O=c1c2ccccc2c(Br)nn1-c1ccc(S(=O)c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3b5cbdaddb17473fa653398223052303 | CC(C)(C)c1ccc(-n2nc(Br)c3cc([N+](=O)[O-])ccc3c2=O)cc1.Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc([N+](=O)[O-])ccc23)n(C(C)(C)C)n1>>Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc(NC=O)ccc23)[nH]n1 | [N+](=O)([O-])C=1C=C2C(=NN(C(C2=CC1)=O)C1=CC=C(C=C1)C(C)(C)C)NC=1N(N=C(C1)C)C(C)(C)C.[N+](=O)([O-])C1=CC=C2C(=NN(C(C2=C1)=O)C1=CC=C(C=C1)C(C)(C)C)NC=1N(N=C(C1)C)C(C)(C)C.BrC1=NN(C(C2=CC=C(C=C12)[N+](=O)[O-])=O)C1=CC=C(C=C1)C(C)(C)C.BrC1=NN(C(C2=CC(=CC=C12)[N+](=O)[O-])=O)C1=CC=C(C=C1)C(C)(C)C.C(C)(C)(C)N1N=C(C=C1N)C.C(... | O=[N+]([O-])c1cc[c:21]2[c:19](=[O:20])[n:8](-[c:9]3[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]3)[n:7][c:6](Br)[c:29]2[cH:28]1.CC(C)(C)c1ccc(-n2nc([NH:5][c:4]3[cH:3][c:2]([CH3:1])[n:31][n:30]3C(C)(C)C)c3c[cH:27][c:23]([N+:24](=O)[O-])[cH:22]c3c2=O)cc1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7... | CC(C)(C)c1ccc(-n2nc(Br)c3cc([N+](=O)[O-])ccc3c2=O)cc1.Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc([N+](=O)[O-])ccc23)n(C(C)(C)C)n1 | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc(NC=O)ccc23)[nH]n1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O1CCOCC1.C(Cl)Cl | Acylation | OtherReaction | 5906b665aa1200c2bcacb28b526344ab523fc470edb36a76aa7587345beab6a8 | 00d2435902a2dab22b2847314e5d2ae0ea735ac21e786faac8cd8893a73550e4 | O=c1c2ccccc2c(Nc2ccn[nH]2)nn1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3](-[c:4]):[c:5](=[O;D1;H0:6]):[c;H0;D3;+0:7]2:c:c:c(-[N+](=O)-[O-]):[cH;D2;+0:8]:[c:9]:2:1.C-C(-C)(-C)-[n;H0;D3;+0:10]1:[#7;a:11]:[c:12]:[c:13]:[c:14]:1-[NH;D2;+0:15]-c1:n:n(-c2:c:c:c(-C(-C)(-C)-C):c:c:2):c(=O):c2:[cH;D2;+0:16]:[c:17](-[N+;H0;D3:18](=O)-[O-]):[cH;D2;+0:19]:c:c:1:2>>[O... | null | [] | null | null | 2 | HOUR | 6-Nitro-4-(2-tert-butyl-5-methyl-2H-pyrazol-3-ylamino)-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one and 7-Nitro-4-(2-tert-butyl-5-methyl-2H-pyrazol-3-ylamino)-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one: 4.56 g of a 1:1 mixture of 4-Bromo-2-(4-tert-butyl-phenyl)-6-nitro-2H-phthalazin-1-one and 4-Bromo-2-(4-tert-butyl-ph... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitro group.Nitro group.Secondary amine | Secondary amide.Secondary amine | c1ccc2cnncc2c1.c1ccccc1.c1cc[nH]n1.c1ccc2cnncc2c1 | c1cn[nH]c1.c1ccc2cnncc2c1 | c1cn[nH]c1.c1ccccc1.c1ccc2cnncc2c1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1.C(Cl)Cl | null | 2 | CC(C)(C)c1ccc(-n2nc(Br)c3cc([N+](=O)[O-])ccc3c2=O)cc1.Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc([N+](=O)[O-])ccc23)n(C(C)(C)C)n1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCOCC1.C(Cl)Cl>Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc(NC... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fd6f54c7484f461ba2f808382012ecd5 | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc([N+](=O)[O-])ccc23)n(C(C)(C)C)n1>>Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc(N)ccc23)n(C(C)(C)C)n1 | [N+](=O)([O-])C1=CC=C2C(=NN(C(C2=C1)=O)C1=CC=C(C=C1)C(C)(C)C)NC=1N(N=C(C1)C)C(C)(C)C>>NC1=CC=C2C(=NN(C(C2=C1)=O)C1=CC=C(C=C1)C(C)(C)C)NC=1N(N=C(C1)C)C(C)(C)C | O=[N+:24]([O-])[c:23]1[cH:22][c:21]2[c:19](=[O:20])[n:8](-[c:9]3[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]3)[n:7][c:6]([NH:5][c:4]3[cH:3][c:2]([CH3:1])[n:33][n:28]3[C:29]([CH3:30])([CH3:31])[CH3:32])[c:27]2[cH:26][cH:25]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11]... | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc([N+](=O)[O-])ccc23)n(C(C)(C)C)n1 | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc(N)ccc23)n(C(C)(C)C)n1 | null | [Pd] | CO.C1CCOC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1c2ccccc2c(Nc2ccn[nH]2)nn1-c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 66.7 | [{"value": 66.7, "product": "NC1=CC=C2C(=NN(C(C2=C1)=O)C1=CC=C(C=C1)C(C)(C)C)NC=1N(N=C(C1)C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.00 g of 7-Nitro-4-(2-tert-butyl-5-methyl-2H-pyrazol-3-ylamino)-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one were hydrogenated over palladium on charcoal in MeOH/THF 1:1 at RT. After completion of the reaction the catalyst was filtered off and the filtrate evaporated. The residue was dissolved in 50 ml DCM and extracte... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cc[nH]n1.c1ccccc1.c1ccc2cnncc2c1 | Other | [Pd].CO.C1CCOC1 | null | null | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc([N+](=O)[O-])ccc23)n(C(C)(C)C)n1>[Pd].CO.C1CCOC1>Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc(N)ccc23)n(C(C)(C)C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5d40a00290b843bfb559cceec1d3acca | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc(NC=O)ccc23)[nH]n1>>Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc(N)ccc23)[nH]n1 | C(C)(C)(C)C1=CC=C(C=C1)N1N=C(C2=CC=C(C=C2C1=O)NC=O)NC=1NN=C(C1)C>>NC1=CC=C2C(=NN(C(C2=C1)=O)C1=CC=C(C=C1)C(C)(C)C)NC=1NN=C(C1)C | O=C[NH:24][c:23]1[cH:22][c:21]2[c:19](=[O:20])[n:8](-[c:9]3[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]3)[n:7][c:6]([NH:5][c:4]3[cH:3][c:2]([CH3:1])[n:29][nH:28]3)[c:27]2[cH:26][cH:25]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:... | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc(NC=O)ccc23)[nH]n1 | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc(N)ccc23)[nH]n1 | null | null | Cl.CO | Reduction | Reduction of primary amides to amines | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | O=c1c2ccccc2c(Nc2ccn[nH]2)nn1-c1ccccc1 | O=C-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 47.6 | [{"value": 47.6, "product": "NC1=CC=C2C(=NN(C(C2=C1)=O)C1=CC=C(C=C1)C(C)(C)C)NC=1NN=C(C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 2 | HOUR | 9 mg of N-[3-(4-tert-Butyl-phenyl)-1-(5-methyl-2H-pyrazol-3-ylamino)-4-oxo-3,4-dihydro-phthalazin-6-yl]-formamide (ZB-1) in a mixture of 0.5 ml MeOH and 0.5 ml conc. HCl were stirred at 50° C. for 2 hrs. The mixture was evaporated under vacuum and the residue dissolved in DCM. The DCM solution was washed with sodium bi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1cn[nH]c1.c1ccccc1.c1ccc2cnncc2c1 | Other | Cl.CO | 50 | 2 | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc(NC=O)ccc23)[nH]n1>Cl.CO>Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc(N)ccc23)[nH]n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5fbb753d030045f8a4265ae61d012b82 | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc([N+](=O)[O-])ccc23)n(C(C)(C)C)n1>>Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc([N+](=O)[O-])ccc23)[nH]n1 | [N+](=O)([O-])C1=CC=C2C(=NN(C(C2=C1)=O)C1=CC=C(C=C1)C(C)(C)C)NC=1N(N=C(C1)C)C(C)(C)C>>C(C)(C)(C)C1=CC=C(C=C1)N1C(C2=CC(=CC=C2C(=N1)NC=1NN=C(C1)C)[N+](=O)[O-])=O | CC(C)(C)[n:30]1[c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]3)[c:19](=[O:20])[c:21]3[cH:22][c:23]([N+:24](=[O:25])[O-:26])[cH:27][cH:28][c:29]23)[cH:3][c:2]([CH3:1])[n:31]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11][c:12]([C:13]([C... | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc([N+](=O)[O-])ccc23)n(C(C)(C)C)n1 | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc([N+](=O)[O-])ccc23)[nH]n1 | null | null | C(=O)O | Deprotection | OtherReaction | a0192af0b7511f6d6cc432f36bd9f28eece2b654e788b7bbcaff6ec5f5442d28 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=c1c2ccccc2c(Nc2ccn[nH]2)nn1-c1ccccc1 | C-C(-C)(-C)-[n;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1-[#7:6]>>[#7:6]-[c:5]1:[c:4]:[c:3]:[#7;a:2]:[nH;D2;+0:1]:1 | 52.9 | [{"value": 52.9, "product": "C(C)(C)(C)C1=CC=C(C=C1)N1C(C2=CC(=CC=C2C(=N1)NC=1NN=C(C1)C)[N+](=O)[O-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 15 mg 7-Nitro-4-(2-tert-butyl-5-methyl-2H-pyrazol-3-ylamino)-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one (preparation see ZB-1) were deprotected by heating in formic acid as described for ZA-1. Evaporation of excess formic acid and chromatography of the residue on silica, eluting with DCM and then with DCM/MeOH 20:1 ga... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc[nH]n1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.c1ccc2cnncc2c1 | Other | C(=O)O | null | null | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc([N+](=O)[O-])ccc23)n(C(C)(C)C)n1>C(=O)O>Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3cc([N+](=O)[O-])ccc23)[nH]n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4d2a16ac4db64a7eb03b9bf96a70c771 | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc([N+](=O)[O-])cc23)n(C(C)(C)C)n1>>Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc([N+](=O)[O-])cc23)[nH]n1 | [N+](=O)([O-])C=1C=C2C(=NN(C(C2=CC1)=O)C1=CC=C(C=C1)C(C)(C)C)NC=1N(N=C(C1)C)C(C)(C)C>>C(C)(C)(C)C1=CC=C(C=C1)N1C(C2=CC=C(C=C2C(=N1)NC=1NN=C(C1)C)[N+](=O)[O-])=O | CC(C)(C)[n:30]1[c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]3)[c:19](=[O:20])[c:21]3[cH:22][cH:23][c:24]([N+:25](=[O:26])[O-:27])[cH:28][c:29]23)[cH:3][c:2]([CH3:1])[n:31]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11][c:12]([C:13]([C... | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc([N+](=O)[O-])cc23)n(C(C)(C)C)n1 | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc([N+](=O)[O-])cc23)[nH]n1 | null | null | C(=O)O | Deprotection | OtherReaction | a0192af0b7511f6d6cc432f36bd9f28eece2b654e788b7bbcaff6ec5f5442d28 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=c1c2ccccc2c(Nc2ccn[nH]2)nn1-c1ccccc1 | C-C(-C)(-C)-[n;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1-[#7:6]>>[#7:6]-[c:5]1:[c:4]:[c:3]:[#7;a:2]:[nH;D2;+0:1]:1 | 47.3 | [{"value": 47.3, "product": "C(C)(C)(C)C1=CC=C(C=C1)N1C(C2=CC=C(C=C2C(=N1)NC=1NN=C(C1)C)[N+](=O)[O-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 12 mg 6-Nitro-4-(2-tert-butyl-5-methyl-2H-pyrazol-3-ylamino)-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one (preparation see ZB-1) were deprotected by heating in formic acid as described for ZB-1. Evaporation of excess formic acid and chromatography of the residue on silica, eluting with DCM and then with DCM/MeOH 20:1 ga... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc[nH]n1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.c1ccc2cnncc2c1 | Other | C(=O)O | null | null | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc([N+](=O)[O-])cc23)n(C(C)(C)C)n1>C(=O)O>Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc([N+](=O)[O-])cc23)[nH]n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b82cdfe163a4f2cb12154477545a3b7 | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc(N)cc23)n(C(C)(C)C)n1>>Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc(N)cc23)[nH]n1 | NC=1C=C2C(=NN(C(C2=CC1)=O)C1=CC=C(C=C1)C(C)(C)C)NC=1N(N=C(C1)C)C(C)(C)C.Cl>>NC=1C=C2C(=NN(C(C2=CC1)=O)C1=CC=C(C=C1)C(C)(C)C)NC=1NN=C(C1)C | CC(C)(C)[n:28]1[c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]3)[c:19](=[O:20])[c:21]3[cH:22][cH:23][c:24]([NH2:25])[cH:26][c:27]23)[cH:3][c:2]([CH3:1])[n:29]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15... | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc(N)cc23)n(C(C)(C)C)n1 | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc(N)cc23)[nH]n1 | null | null | CO | Deprotection | OtherReaction | a0192af0b7511f6d6cc432f36bd9f28eece2b654e788b7bbcaff6ec5f5442d28 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=c1c2ccccc2c(Nc2ccn[nH]2)nn1-c1ccccc1 | C-C(-C)(-C)-[n;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1-[#7:6]>>[#7:6]-[c:5]1:[c:4]:[c:3]:[#7;a:2]:[nH;D2;+0:1]:1 | 45.8 | [{"value": 45.8, "product": "NC=1C=C2C(=NN(C(C2=CC1)=O)C1=CC=C(C=C1)C(C)(C)C)NC=1NN=C(C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 30 mg 6-amino-4-(2-tert-butyl-5-methyl-2H-pyrazol-3-ylamino)-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one were dissolved in 0.5 ml MeOH. 2 ml conc. HCl were added and the mixture was heated to 80° C. for 7 hrs. The mixture was evaporated under vacuum, the residue dissolved in DCM and washed with sodium bicarbonate solut... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc[nH]n1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.c1ccc2cnncc2c1 | Other | CO | 80 | null | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc(N)cc23)n(C(C)(C)C)n1>CO>Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc(N)cc23)[nH]n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c316b6106d424f979bd720905c4400ca | CC(C)(C)c1ccc(-n2nc(Br)c3cc(Br)ccc3c2=O)cc1.Cc1cc(N)n(C(C)(C)C)n1>>Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc(Br)cc23)n(C(C)(C)C)n1 | BrC1=NN(C(C2=CC=C(C=C12)Br)=O)C1=CC=C(C=C1)C(C)(C)C.C(C)(C)(C)N1N=C(C=C1N)C.C([O-])([O-])=O.[Cs+].[Cs+].C1(=CC=CC=C1)P(C1=CC=CC=2C(C3=CC=CC(=C3OC12)P(C1=CC=CC=C1)C1=CC=CC=C1)(C)C)C1=CC=CC=C1>>BrC=1C=C2C(=NN(C(C2=CC1)=O)C1=CC=C(C=C1)C(C)(C)C)NC=1N(N=C(C1)C)C(C)(C)C | Br[c:6]1[n:7][n:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]2)[c:19](=[O:20])[c:21]2[cH:22][cH:23][c:24]([Br:25])[cH:26][c:27]12.[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:28]([C:29]([CH3:30])([CH3:31])[CH3:32])[n:33]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11][c... | CC(C)(C)c1ccc(-n2nc(Br)c3cc(Br)ccc3c2=O)cc1.Cc1cc(N)n(C(C)(C)C)n1 | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc(Br)cc23)n(C(C)(C)C)n1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | df3bfedad2a7f0f256464ab6dcf71ec93640ec0ccd579b3524f93860b3777b00 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1c2ccccc2c(Nc2ccn[nH]2)nn1-c1ccccc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3](-[c:4]):[c:5]:[c:6]:[c:7]:1:[c:8].[C:9]-[#7;a:10]1:[#7;a:11]:[c:12]:[c:13]:[c:14]:1-[NH2;D1;+0:15]>>[C:9]-[#7;a:10]1:[#7;a:11]:[c:12]:[c:13]:[c:14]:1-[NH;D2;+0:15]-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3](-[c:4]):[c:5]:[c:6]:[c:7]:1:[c:8] | 194.9 | [{"value": 194.9, "product": "BrC=1C=C2C(=NN(C(C2=CC1)=O)C1=CC=C(C=C1)C(C)(C)C)NC=1N(N=C(C1)C)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 20 | HOUR | 11 mg 4,6-Dibromo-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one (preparation see ZA-1) were reacted with 39.0 mg 1-tert.-butyl-3-methyl-1H-pyrazol-5-ylamine, 132 mg cesium carbonate, 7.0 mg tris-(dibenzylideneacetone)-dipalladium and 8.8 mg 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene were stirred under argon at 100° ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | c1cc[nH]n1.c1ccccc1.c1ccc2cnncc2c1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | 100 | 20 | CC(C)(C)c1ccc(-n2nc(Br)c3cc(Br)ccc3c2=O)cc1.Cc1cc(N)n(C(C)(C)C)n1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]>Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc(Br)cc23)n(C(C)(C)C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e73b737e13e0450d8d66130b22ebe6c8 | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc(Br)cc23)n(C(C)(C)C)n1>>Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc(Br)cc23)[nH]n1 | BrC=1C=C2C(=NN(C(C2=CC1)=O)C1=CC=C(C=C1)C(C)(C)C)NC=1N(N=C(C1)C)C(C)(C)C>>BrC=1C=C2C(=NN(C(C2=CC1)=O)C1=CC=C(C=C1)C(C)(C)C)NC=1NN=C(C1)C | CC(C)(C)[n:28]1[c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]3)[c:19](=[O:20])[c:21]3[cH:22][cH:23][c:24]([Br:25])[cH:26][c:27]23)[cH:3][c:2]([CH3:1])[n:29]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8](-[c:9]3[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15]... | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc(Br)cc23)n(C(C)(C)C)n1 | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc(Br)cc23)[nH]n1 | null | null | C(=O)O | Deprotection | OtherReaction | a0192af0b7511f6d6cc432f36bd9f28eece2b654e788b7bbcaff6ec5f5442d28 | 30a26bc929988d0041b9998cdccd1d65eb125114a78065ed35d40f50c965c0a7 | O=c1c2ccccc2c(Nc2ccn[nH]2)nn1-c1ccccc1 | C-C(-C)(-C)-[n;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1-[#7:6]>>[#7:6]-[c:5]1:[c:4]:[c:3]:[#7;a:2]:[nH;D2;+0:1]:1 | null | [] | null | null | null | null | 15 mg of 6-Bromo-4-(2-tert-butyl-5-methyl-2H-pyrazol-3-ylamino)-2-(4-tert-butyl-phenyl)-2H-phthalazin-1-one were heated in formic acid for 5 hrs at 90° C., then evaporated and chromatographed on silica (DCM, then DCM/MeOH 40:1). Yield 10 mg. 1H-NMR: (400 MHz, D6-DMSO) 9.33 (1H, br s), 8.86 (1H, br s), 8.26 (1H, d), 8.8... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc[nH]n1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.c1ccc2cnncc2c1 | Other | C(=O)O | null | null | Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc(Br)cc23)n(C(C)(C)C)n1>C(=O)O>Cc1cc(Nc2nn(-c3ccc(C(C)(C)C)cc3)c(=O)c3ccc(Br)cc23)[nH]n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-08aa941a4c3d4dc4bcd7a1998e8308f1 | CC(C)Br.O=c1[nH]nc(Br)c2ccc([N+](=O)[O-])cc12>>CC(C)n1nc(Br)c2ccc([N+](=O)[O-])cc2c1=O | [H-].[Na+].BrC(C)C.[N+](=O)([O-])C=1C=C2C(=NNC(C2=CC1)=O)Br.[N+](=O)([O-])C1=CC=C2C(=NNC(C2=C1)=O)Br.[H-].[Na+]>>[N+](=O)([O-])C1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br | Br[CH:2]([CH3:1])[CH3:3].[nH:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]2[c:17]1=[O:18]>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]2[c:17]1=[O:18] | CC(C)Br.O=c1[nH]nc(Br)c2ccc([N+](=O)[O-])cc12 | CC(C)n1nc(Br)c2ccc([N+](=O)[O-])cc2c1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 9cdd026cfffefe57c026cfbe63ea07a00fa0efedbda74a2a161f9146dc75dbb7 | 3456c966f3f7e7d410f206842ab08ae4d1cfab4368ca2a0de7a6ad251462e6f4 | O=c1[nH]ncc2ccccc12 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[O;D1;H0:4]=[c:5](:[c:6]):[nH;D2;+0:7]:[#7;a:8]:[c:9]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[n;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:5](=[O;D1;H0:4]):[c:6] | 40 | [{"value": 40.0, "product": "[N+](=O)([O-])C1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of 6-nitro-4-bromo-2H-phthalazin-1-one and 7-nitro-4-bromo-2H-phthalazin-1-one (84 g, 0.31 mol) was dissolved in DMF (400 ml). To this was added NaH (60%, 7.5 g, 0.31 mol) as a DMF suspension (200 ml). The mixture was stirred at RT for 30 min then 2-bromo-propane (7.7 g, 62 mmol) was added in one portion as a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | null | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | HBr | CN(C)C=O | null | 0.5 | CC(C)Br.O=c1[nH]nc(Br)c2ccc([N+](=O)[O-])cc12>CN(C)C=O>CC(C)n1nc(Br)c2ccc([N+](=O)[O-])cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-82d4fcbba7f241208f050b6169693c8f | CC(C)n1nc(Br)c2ccc([N+](=O)[O-])cc2c1=O>>CC(C)n1nc(Br)c2ccc(N)cc2c1=O | [N+](=O)([O-])C1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br.Cl>>NC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]2[c:6]([Br:7])[n:5][n:4]([CH:2]([CH3:1])[CH3:3])[c:15](=[O:16])[c:14]2[cH:13]1>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:13][c:14]2[c:15]1=[O:16] | CC(C)n1nc(Br)c2ccc([N+](=O)[O-])cc2c1=O | CC(C)n1nc(Br)c2ccc(N)cc2c1=O | null | [Fe] | O.CCO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1[nH]ncc2ccccc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99.2 | [{"value": 98.0, "product": "NC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.2, "product": "NC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 7-Nitro-2-isopropyl-4-bromo-2H-phthalazin-1-one (4.6 g, 0.015 mol) was dissolved in a 5:1 mixture of EtOH and water (150 ml). To this solution was added iron powder (2.14 g, 0.039 mol) and concentrated HCl (1 ml), the mixture was heated to 80° C. for 3 hours. After this time, the reaction mixture was cooled to RT and f... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2cnncc2c1 | Other | [Fe].O.CCO | 80 | null | CC(C)n1nc(Br)c2ccc([N+](=O)[O-])cc2c1=O>[Fe].O.CCO>CC(C)n1nc(Br)c2ccc(N)cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0f65da7aec364288b45928dda596e908 | CC(C)n1nc(Br)c2ccc(N)cc2c1=O.NC(N)=O>>CC(C)n1nc(Br)c2ccc(O)cc2c1=O | S(O)(O)(=O)=O.S(O)(O)(=O)=O.NC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br.NC(=O)N.N(=O)[O-].[Na+]>>OC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br | N[c:11]1[cH:10][cH:9][c:8]2[c:6]([Br:7])[n:5][n:4]([CH:2]([CH3:1])[CH3:3])[c:15](=[O:16])[c:14]2[cH:13]1.NC(N)=[O:12]>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:13][c:14]2[c:15]1=[O:16] | CC(C)n1nc(Br)c2ccc(N)cc2c1=O.NC(N)=O | CC(C)n1nc(Br)c2ccc(O)cc2c1=O | null | null | O.CC(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | cfab2f484739552aa5b4f343f8242b28711d19942fda9cb68cb2f81405944162 | 891ec3b13223a598ccf2a9d11ebe28aad97dbcc6e0037050822ea9d225a1dca7 | O=c1[nH]ncc2ccccc12 | N-C(-N)=[O;H0;D1;+0:1].N-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]:[c:7]:[#7;a:8]>>[#7;a:8]:[c:7]:[c:6]:[c:5]:[c;H0;D3;+0:2](-[OH;D1;+0:1]):[c:3]:[c:4] | 93.2 | [{"value": 93.0, "product": "OC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.2, "product": "OC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | Concentrated sulfuric acid (17 ml) was added slowly to a solution of 7-amino-2-isopropyl-4-bromo-2H-phthalazin-1-one (4.6 g, 0.016 mol) in HOAc (50 ml). The reaction mixture was cooled to 0° C. and a solution of sodium nitrite (1.52 g, 0.022 mol) in water (10 ml) was added dropwise. The reaction mixture was stirred for... | 10.6084/m9.figshare.5104873.v1 | null | Urea.Primary amine | Aromatic alcohol | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | Other | O.CC(=O)O | 0 | 0.333333 | CC(C)n1nc(Br)c2ccc(N)cc2c1=O.NC(N)=O>O.CC(=O)O>CC(C)n1nc(Br)c2ccc(O)cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5068cdcca80b424da091e6122b654003 | CC(C)n1nc(Br)c2ccc(O)cc2c1=O.CSCCCl>>CSCCOc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | CSCCCl.OC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br.C([O-])([O-])=O.[K+].[K+]>>BrC1=NN(C(C2=CC(=CC=C12)OCCSC)=O)C(C)C | [OH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([Br:11])[n:12][n:13]([CH:14]([CH3:15])[CH3:16])[c:17](=[O:18])[c:19]2[cH:20]1.Cl[CH2:4][CH2:3][S:2][CH3:1]>>[CH3:1][S:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([Br:11])[n:12][n:13]([CH:14]([CH3:15])[CH3:16])[c:17](=[O:18])[c:19]2[cH:20]1 | CC(C)n1nc(Br)c2ccc(O)cc2c1=O.CSCCCl | CSCCOc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=c1[nH]ncc2ccccc12 | Cl-[CH2;D2;+0:1]-[C:2]-[#16:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#16:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 30 | [{"value": 24.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)OCCSC)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)OCCSC)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | MINUTE | To a solution of 7-hydroxy-2-isopropyl-4-bromo-2H-phthalazin-1-one (0.8 g, 0.0028 mol) in DMF (8 ml), was added potassium carbonate (2 g, 0.014 mol). After 5 min, 2-chloroethyl methyl sulfide (0.34 g, 0.0028 mol) was added and the solution was heated to 100° C. for 24 hours. After this time LC-MS indicated the complete... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2cnncc2c1 | HCl | CN(C)C=O | 100 | 0.083333 | CC(C)n1nc(Br)c2ccc(O)cc2c1=O.CSCCCl>CN(C)C=O>CSCCOc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-be436706b01948fcb9adab5d833f4aae | CSCCOc1ccc2c(Br)nn(C(C)C)c(=O)c2c1.Cc1cc(N)n[nH]1>>CSCCOc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1 | BrC1=NN(C(C2=CC(=CC=C12)OCCSC)=O)C(C)C.CC(C)([O-])C.[Na+].NC1=NNC(=C1)C.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C>>C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)OCCSC)=O | Br[c:10]1[c:9]2[cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][S:2][CH3:1])[cH:26][c:25]2[c:23](=[O:24])[n:19]([CH:20]([CH3:21])[CH3:22])[n:18]1.[NH2:11][c:12]1[cH:13][c:14]([CH3:15])[nH:16][n:17]1>>[CH3:1][S:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([NH:11][c:12]3[cH:13][c:14]([CH3:15])[nH:16][n:17]3)[n:18][n:19]([CH:... | CSCCOc1ccc2c(Br)nn(C(C)C)c(=O)c2c1.Cc1cc(N)n[nH]1 | CSCCOc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C(C)OCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | df3bfedad2a7f0f256464ab6dcf71ec93640ec0ccd579b3524f93860b3777b00 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=c1[nH]nc(Nc2cc[nH]n2)c2ccccc12 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3](-[C:4]):[c:5]:[c:6]:[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10]1:[#7;a:11]:[#7;a:12]:[c:13]:[c:14]:1>>[C:4]-[#7;a:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:9]-[c:10]2:[#7;a:11]:[#7;a:12]:[c:13]:[c:14]:2):[c:7](:[c:8]):[c:6]:[c:5]:1 | 23.4 | [{"value": 7.0, "product": "C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)OCCSC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.4, "product": "C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)OCCSC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | Degassed toluene (6 ml) and EtOH (3 ml) were added in one portion to a mixture of 4-bromo-2-isopropyl-7-(2-methylsulfanyl-ethoxy)-2H-phthalazin-1-one (0.3 g, 0.8 mmol), sodium t-butoxide (0.112 g, 1.2 mmol), 3-amino-5-methyl pyrazole (0.107 g, 1.2 mmol), tris-(dibenzylideneacetone)-dipalladium (0.038 g, 0.042 mmol) and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | c1cn[nH]c1.c1ccc2cnncc2c1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C(C)OCC | 100 | null | CSCCOc1ccc2c(Br)nn(C(C)C)c(=O)c2c1.Cc1cc(N)n[nH]1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C(C)OCC>CSCCOc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ced49b7e30a54950abb6c681fcae2c93 | CSCCOc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1.O=C(OO)c1cccc(Cl)c1>>Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(OCCS(C)=O)ccc23)n[nH]1 | C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)OCCSC)=O.ClC=1C=C(C(=O)OO)C=CC1>>C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)OCCS(=O)C)=O | [CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8]([CH:9]([CH3:10])[CH3:11])[c:12](=[O:13])[c:14]3[cH:15][c:16]([O:17][CH2:18][CH2:19][S:20][CH3:21])[cH:23][cH:24][c:25]23)[n:26][nH:27]1.O=C(O[OH:22])c1cccc(Cl)c1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8]([CH:9]([CH3:10])[CH3:11])[c:12](=[O:13])[c:14]3[cH:15][c:16](... | CSCCOc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1.O=C(OO)c1cccc(Cl)c1 | Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(OCCS(C)=O)ccc23)n[nH]1 | null | null | C(Cl)Cl | Oxidation | Sulfanyl to sulfinyl_peroxide | 95b5106b07a173d8eafc1c9c8a6c938befe131c3d1caaf5886529b7aee55ea9d | 7652b53bb02130dccfe4b1e8905d7f3db7f05ff3a95a0003c1bab09b1ad4083e | O=c1[nH]nc(Nc2cc[nH]n2)c2ccccc12 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[C:2]-[C:3]-[S;H0;D2;+0:4]-[C;D1;H3:5]>>[C:2]-[C:3]-[S;H0;D3;+0:4](-[C;D1;H3:5])=[O;H0;D1;+0:1] | 16.7 | [{"value": 14.0, "product": "C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)OCCS(=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.7, "product": "C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)OCCS(=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2-isopropyl-4-(5-methyl-1H-pyrazol-3-ylamino)-7-(2-methylsulfanyl-ethoxy)-2H-phthalazin-1-one (0.077 g, 0.23 mmol) in DCM (2 ml), was added m-chloro-peroxybenzoic acid (0.040 g, 0.23 mmol) portion wise. The solution was stirred at RT for 1 hour. After this time LC-MS indicated complete consumption of s... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide.Monosulfide | Sulfoxide | c1ccccc1 | null | c1cn[nH]c1.c1ccc2cnncc2c1 | HCl | C(Cl)Cl | null | 1 | CSCCOc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(OCCS(C)=O)ccc23)n[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1860911f12d94f24bc465153aac55072 | CNc1ccc2c(Br)nn(C(C)C)c(=O)c2c1.CSCCCl>>CSCCN(C)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | O.CSCCCl.BrC1=NN(C(C2=CC(=CC=C12)NC)=O)C(C)C.[H-].[Na+]>>BrC1=NN(C(C2=CC(=CC=C12)N(CCSC)C)=O)C(C)C | [NH:5]([CH3:6])[c:7]1[cH:8][cH:9][c:10]2[c:11]([Br:12])[n:13][n:14]([CH:15]([CH3:16])[CH3:17])[c:18](=[O:19])[c:20]2[cH:21]1.Cl[CH2:4][CH2:3][S:2][CH3:1]>>[CH3:1][S:2][CH2:3][CH2:4][N:5]([CH3:6])[c:7]1[cH:8][cH:9][c:10]2[c:11]([Br:12])[n:13][n:14]([CH:15]([CH3:16])[CH3:17])[c:18](=[O:19])[c:20]2[cH:21]1 | CNc1ccc2c(Br)nn(C(C)C)c(=O)c2c1.CSCCCl | CSCCN(C)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=c1[nH]ncc2ccccc12 | Cl-[CH2;D2;+0:1]-[C:2]-[#16:3].[C;D1;H3:4]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[#16:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:5](-[C;D1;H3:4])-[c:6](:[c:7]):[c:8] | 18 | [{"value": 18.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)N(CCSC)C)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.7, "product": "BrC1=NN(C(C2=CC(=CC=C12)N(CCSC)C)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 4-Bromo-2-isopropyl-7-methylamino-2H-phthalazin-1-one (0.095 g, 0.32 mmol) was dissolved in DMF (5 ml). To this was added NaH (60%, 0.015 g, 0.38 mmol) as a suspension in DMF (2 ml). The mixture was stirred at RT for 30 min then chloroethyl methyl sulfide (0.042 g, 0.38 mmol) was added in one portion as a solution in D... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccc2cnncc2c1 | HCl | CN(C)C=O | null | 0.5 | CNc1ccc2c(Br)nn(C(C)C)c(=O)c2c1.CSCCCl>CN(C)C=O>CSCCN(C)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-125e173b9c06410c8c1d292b9a52e61f | CC(C)n1nc(Br)c2ccc(N)cc2c1=O>>CC(C)n1nc(Br)c2ccc(S)cc2c1=O | NC(=O)N.O(C(=S)[S-])CC.[K+].[OH-].[Na+].Cl.S(O)(O)(=O)=O.NC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br.N(=O)[O-].[Na+]>>SC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br | N[c:11]1[cH:10][cH:9][c:8]2[c:6]([Br:7])[n:5][n:4]([CH:2]([CH3:1])[CH3:3])[c:15](=[O:16])[c:14]2[cH:13]1>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([SH:12])[cH:13][c:14]2[c:15]1=[O:16] | CC(C)n1nc(Br)c2ccc(N)cc2c1=O | CC(C)n1nc(Br)c2ccc(S)cc2c1=O | null | null | O.CC(=O)O.C(Cl)Cl | Functional Group Interconversion | OtherReaction | ca2588dce952a1b38d55c09e7b0383f4664bdfa6a4f49cfbfbed4e37e3a612af | 87c716ea3b1c83749a8df825a73e64f71848c6f0dfcd36a842cec45d5ae0fe3c | O=c1[nH]ncc2ccccc12 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]:[c:4]:[c;H0;D3;+0:1](-[S;D1;H1:8]):[c:2]:[c:3] | 48.6 | [{"value": 48.0, "product": "SC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.6, "product": "SC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | Concentrated sulfuric acid (5 ml) was added dropwise to a solution of 7-amino-2-isopropyl-4-bromo-2H-phthalazin-1-one (1.5 g, 5.3 mmol) in HOAc (15 ml) and the solution was cooled to 0° C. A solution of sodium nitrite (0.5 g, 7.4 mmol) in water (2.5 ml) was added dropwise and the reaction mixture was stirred at 0° C. f... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic thiol | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | null | O.CC(=O)O.C(Cl)Cl | 0 | 0.333333 | CC(C)n1nc(Br)c2ccc(N)cc2c1=O>O.CC(=O)O.C(Cl)Cl>CC(C)n1nc(Br)c2ccc(S)cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-20e7de7e885c432b9e6b3aef80ba8188 | CC(C)n1nc(Br)c2ccc(S)cc2c1=O.CSCCCl>>CSCCSc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | ClCCSC.SC1=CC=C2C(=NN(C(C2=C1)=O)C(C)C)Br.[H-].[Na+]>>BrC1=NN(C(C2=CC(=CC=C12)SCCSC)=O)C(C)C | [SH:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([Br:11])[n:12][n:13]([CH:14]([CH3:15])[CH3:16])[c:17](=[O:18])[c:19]2[cH:20]1.Cl[CH2:4][CH2:3][S:2][CH3:1]>>[CH3:1][S:2][CH2:3][CH2:4][S:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([Br:11])[n:12][n:13]([CH:14]([CH3:15])[CH3:16])[c:17](=[O:18])[c:19]2[cH:20]1 | CC(C)n1nc(Br)c2ccc(S)cc2c1=O.CSCCCl | CSCCSc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | O=c1[nH]ncc2ccccc12 | Cl-[CH2;D2;+0:1]-[C:2]-[#16:3].[SH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#16:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 90.7 | [{"value": 54.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)SCCSC)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.7, "product": "BrC1=NN(C(C2=CC(=CC=C12)SCCSC)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 5 | MINUTE | To a solution of crude 7-mercapto-2-isopropyl-4-bromo-2H-phthalazin-1-one (0.40 g, 1.3 mmol) in DMF (8 ml), was added NaH (60%, 0.064 g, 1.6 mmol) portion-wise. After stirring for 5 min, chloroethyl methylsulfide (0.17 g, 1.6 mmol) was added dropwise. The mixture was heated to 60° C. for two hours, after which time the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccc2cnncc2c1 | HCl | CN(C)C=O | 60 | 0.083333 | CC(C)n1nc(Br)c2ccc(S)cc2c1=O.CSCCCl>CN(C)C=O>CSCCSc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-78510a8ffd544d4f98a1aa1b8f9cdba4 | CSCCSc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1.O.O>>Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(S(=O)(=O)CCS(C)(=O)=O)ccc23)n[nH]1 | O.OOS(=O)[O-].[K+].C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)SCCSC)=O.O1CCOCC1.O>>C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)S(=O)(=O)CCS(=O)(=O)C)=O | [CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8]([CH:9]([CH3:10])[CH3:11])[c:12](=[O:13])[c:14]3[cH:15][c:16]([S:17][CH2:20][CH2:21][S:22][CH3:23])[cH:26][cH:27][c:28]23)[n:29][nH:30]1.[OH2:18].[OH2:25]>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][n:8]([CH:9]([CH3:10])[CH3:11])[c:12](=[O:13])[c:14]3[cH:15][c:16]([S:17](=... | CSCCSc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1.O.O | Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(S(=O)(=O)CCS(C)(=O)=O)ccc23)n[nH]1 | null | null | null | Oxidation | OtherReaction | 4c1073e3ef036e09213d4861abf2fb42a91ab53226c571ff17f5fd22f1926b30 | 07a1b35850329db9760274813b717ea647a40ef1a96eecf857705f567c82b42a | O=c1[nH]nc(Nc2cc[nH]n2)c2ccccc12 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[C:3]-[C:4]-[S;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[OH2;D0;+0:9].[OH2;D0;+0:10]>>[C;D1;H3:1]-[S;H0;D4;+0:2](=[O;D1;H0:11])(=[O;H0;D1;+0:10])-[C:3]-[C:4]-[S;H0;D4;+0:5](=[O;D1;H0:12])(=[O;H0;D1;+0:9])-[c:6](:[c:7]):[c:8] | 57 | [{"value": 57.0, "product": "C(C)(C)N1C(C2=CC(=CC=C2C(=N1)NC1=NNC(=C1)C)S(=O)(=O)CCS(=O)(=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Oxone (0.12 g, 0.07 mmol) was added in one portion to a stirred solution of 2-isopropyl-4-(5-methyl-1H-pyrazol-3-ylamino)-7-(2-methylsulfanyl-ethylsulfanyl)-2H-phthalazin-1-one (0.013 g, 0.03 mmol) in a 4:1 mixture of dioxane/water (1.2 ml) and the reaction mixture was stirred at RT for 1 hour. The reaction mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Monosulfide | Sulfone.Sulfone | null | null | c1cn[nH]c1.c1ccc2cnncc2c1 | null | null | null | 1 | CSCCSc1ccc2c(Nc3cc(C)[nH]n3)nn(C(C)C)c(=O)c2c1.O.O>>Cc1cc(Nc2nn(C(C)C)c(=O)c3cc(S(=O)(=O)CCS(C)(=O)=O)ccc23)n[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b38392a43aac4f7f825e10b1356bb2ff | CC(C)n1nc(Br)c2ccc(NC(=O)OC(C)(C)C)cc2c1=O.CN(C)C=O>>CC(C)n1nc(Br)c2ccc(N(CCN(C)C)C(=O)OC(C)(C)C)cc2c1=O | O.BrCCOC.CN(C)C=O.C(C)(C)(C)OC(NC=1C=C2C(N(N=C(C2=CC1)Br)C(C)C)=O)=O.CN(C)C=O.[H-].[Na+].CN(C)C=O>>C(C)(C)(C)OC(N(CCN(C)C)C=1C=C2C(N(N=C(C2=CC1)Br)C(C)C)=O)=O | [CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([NH:12][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[cH:25][c:26]2[c:27]1=[O:28].O=C[N:15]([CH3:16])[CH3:17]>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([N:12]([CH2:13][CH2:14][N:15]([CH3:16])[CH3:17])[C:18](... | CC(C)n1nc(Br)c2ccc(NC(=O)OC(C)(C)C)cc2c1=O.CN(C)C=O | CC(C)n1nc(Br)c2ccc(N(CCN(C)C)C(=O)OC(C)(C)C)cc2c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | ea77207d9dd23d35a428d665e888028d3d596782db5ec951b7167b17f9d3cddb | f4aef5e36b7682039182b2ffa973f3b4de374d9326293fecb3267c2d72a83935 | O=c1[nH]ncc2ccccc12 | O=C-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C;D1;H3:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#8:8]-[C:9](=[O;D1;H0:10])-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:2]-[N;H0;D3;+0:1](-[C;D1;H3:3])-[C:15]-[C:16]-[N;H0;D3;+0:11](-[C:9](=[O;D1;H0:10])-[#8:8]-[C:5](-[C;D1;H3:4])(-[C;D1;H3:6])-[C;D1;H3:7])-[c:12](:[c:13]):... | 23 | [{"value": 23.0, "product": "C(C)(C)(C)OC(N(CCN(C)C)C=1C=C2C(N(N=C(C2=CC1)Br)C(C)C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | (1-Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazin-6-yl)-carbamic acid tert-butyl ester (0.75 g, 1.96 mmol) was dissolved in DMF (10 ml). To this was added NaH (60%, 0.2 g, 4.9 mmol) as a suspension in DMF (5 ml). The mixture was stirred at RT for 30 min then 1-bromo-2-methoxyethane (0.4 g, 2.9 mmol) was added in one po... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Tertiary amide | Carbamic ester.Tertiary amine | null | null | c1ccc2cnncc2c1 | null | null | null | 0.5 | CC(C)n1nc(Br)c2ccc(NC(=O)OC(C)(C)C)cc2c1=O.CN(C)C=O>>CC(C)n1nc(Br)c2ccc(N(CCN(C)C)C(=O)OC(C)(C)C)cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4422387ee81c4337bcebf4753617b5b4 | NN.O=C(O)c1ccc2c(c1)C(=O)OC2=O>>O=C(O)c1ccc2c(=O)[nH][nH]c(=O)c2c1 | O.NN.C1=CC2=C(C=C1C(=O)O)C(=O)OC2=O>>O=C1NNC(C2=CC(=CC=C12)C(=O)O)=O | [NH2:10][NH2:11].O1[C:8](=[O:9])[c:7]2[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:15][c:14]2[C:12]1=[O:13]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8](=[O:9])[nH:10][nH:11][c:12](=[O:13])[c:14]2[cH:15]1 | NN.O=C(O)c1ccc2c(c1)C(=O)OC2=O | O=C(O)c1ccc2c(=O)[nH][nH]c(=O)c2c1 | null | null | CC(=O)O | Miscellaneous | OtherReaction | 2eb41fd326d947b9a686dc388415f2cdee10671cc3d0a161b79e11b60824f49e | 7bb342cf852a2f6fefb018a30606d65eee2249c97e82671b7539980b110d9a4f | O=c1[nH][nH]c(=O)c2ccccc12 | [NH2;D1;+0:1]-[NH2;D1;+0:2].[O;D1;H0:3]=[C;H0;D3;+0:4]1-O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9]-1:[c:10]>>[O;D1;H0:3]=[c;H0;D3;+0:4]1:[nH;D2;+0:2]:[nH;D2;+0:1]:[c;H0;D3;+0:5](=[O;D1;H0:6]):[c:7](:[c:8]):[c:9]:1:[c:10] | 85 | [{"value": 85.0, "product": "O=C1NNC(C2=CC(=CC=C12)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.9, "product": "O=C1NNC(C2=CC(=CC=C12)C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | Hydrazine hydrate (26 g, 0.52 mol) was added in one portion to a stirred mixture of 1,2,4-benzenetricarboxylic anhydride (100 g, 0.52 mol), in HOAc (1.0 L) at RT. The mixture was heated to 120° C. for 2 h and then allowed to cool to RT. The solid was filtered, washed with water (250 ml) and dried in the under vacuum at... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Anhydride.Ester.Ester | null | c1ccc2c(c1)COC2 | C1=c2ccccc2=CNN1 | C1=c2ccccc2=CNN1 | HO- | CC(=O)O | 120 | null | NN.O=C(O)c1ccc2c(c1)C(=O)OC2=O>CC(=O)O>O=C(O)c1ccc2c(=O)[nH][nH]c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-838951553ef546c1973ea38e16219174 | BrP(Br)(Br)(Br)Br.O=C(O)c1ccc2c(=O)[nH][nH]c(=O)c2c1>>O=C(O)c1ccc2c(Br)n[nH]c(=O)c2c1 | O=C1NNC(C2=CC(=CC=C12)C(=O)O)=O.P(Br)(Br)(Br)(Br)Br>>BrC1=NNC(C2=CC(=CC=C12)C(=O)O)=O | BrP(Br)(Br)(Br)[Br:9].O=[c:8]1[c:7]2[cH:6][cH:5][c:4]([C:2](=[O:1])[OH:3])[cH:15][c:14]2[c:12](=[O:13])[nH:11][nH:10]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([Br:9])[n:10][nH:11][c:12](=[O:13])[c:14]2[cH:15]1 | BrP(Br)(Br)(Br)Br.O=C(O)c1ccc2c(=O)[nH][nH]c(=O)c2c1 | O=C(O)c1ccc2c(Br)n[nH]c(=O)c2c1 | null | null | CC(=O)O.ClCCCl | Functional Group Interconversion | OtherReaction | 5901bbf9fba22c64f3482f65f42eacf0756ea8701e0de77786bd178b73613a5d | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=c1[nH]ncc2ccccc12 | Br-P(-Br)(-Br)(-Br)-[Br;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1:[c:8]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[#7;a:4]:[c:5]:[c:6]:[c:7]:1:[c:8] | 73 | [{"value": 73.0, "product": "BrC1=NNC(C2=CC(=CC=C12)C(=O)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.8, "product": "BrC1=NNC(C2=CC(=CC=C12)C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1,4-Dioxo-1,2,3,4-tetrahydro-phthalazine-6-carboxylic acid (91.0 g, 0.44 mol) was suspended in DCE (1.0 L) and phosphorus pentabromide (761.0 g, 1.77 mol) was added in three portions and the reaction heated to reflux for 24 hours. The reaction was cooled to RT and poured onto ice (2.5 kg) and the resulting precipitate ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | C1=c2ccccc2=CNN1 | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | HBr | CC(=O)O.ClCCCl | null | null | BrP(Br)(Br)(Br)Br.O=C(O)c1ccc2c(=O)[nH][nH]c(=O)c2c1>CC(=O)O.ClCCCl>O=C(O)c1ccc2c(Br)n[nH]c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-51191748fff74f2bbc598516fa53700f | CCO.O=C(O)c1ccc2c(Br)n[nH]c(=O)c2c1>>CCOC(=O)c1ccc2c(Br)n[nH]c(=O)c2c1 | S(O)(O)(=O)=O.BrC1=NNC(C2=CC(=CC=C12)C(=O)O)=O.CCO>>C(C)OC(=O)C=1C=C2C(NN=C(C2=CC1)Br)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([Br:11])[n:12][nH:13][c:14](=[O:15])[c:16]2[cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([Br:11])[n:12][nH:13][c:14](=[O:15])[c:16]2[cH:17]1 | CCO.O=C(O)c1ccc2c(Br)n[nH]c(=O)c2c1 | CCOC(=O)c1ccc2c(Br)n[nH]c(=O)c2c1 | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=c1[nH]ncc2ccccc12 | 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] | 31 | [{"value": 31.0, "product": "C(C)OC(=O)C=1C=C2C(NN=C(C2=CC1)Br)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Concentrated sulfuric acid (40 ml) was added to a stirred solution of 1-bromo-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid (85 g, 0.32 mol) in EtOH (500 ml) and the mixture was heated to reflux for 48 hours. After this time, the reaction mixture was cooled and the resulting precipitate was filtered. The precipitate ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccc2cnncc2c1 | HO- | null | null | null | CCO.O=C(O)c1ccc2c(Br)n[nH]c(=O)c2c1>>CCOC(=O)c1ccc2c(Br)n[nH]c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f9f5d09829445fa868973a8c1b155cd | CC(Br)CO.CCOC(=O)c1ccc2c(Br)n[nH]c(=O)c2c1>>CCOC(=O)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | BrC(CO)C.C(C)OC(=O)C=1C=C2C(NN=C(C2=CC1)Br)=O.[H-].[Na+]>>C(C)OC(=O)C=1C=C2C(N(N=C(C2=CC1)Br)C(C)C)=O | O[CH2:16][CH:14](Br)[CH3:15].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([Br:11])[n:12][nH:13][c:17](=[O:18])[c:19]2[cH:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([Br:11])[n:12][n:13]([CH:14]([CH3:15])[CH3:16])[c:17](=[O:18])[c:19]2[cH:20]1 | CC(Br)CO.CCOC(=O)c1ccc2c(Br)n[nH]c(=O)c2c1 | CCOC(=O)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b13ee664a48205e8588ba2fe6c931f068eed8e0710341d0557b6e0be4fe35def | 2134b0ddabf7bc32ccd75d1ac86b03077ce2dab15f2fd4840f21221cbfe820dd | O=c1[nH]ncc2ccccc12 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-O.[O;D1;H0:4]=[c:5](:[c:6]):[nH;D2;+0:7]:[#7;a:8]:[c:9]>>[C;D1;H3:2]-[CH;D3;+0:1](-[CH3;D1;+0:3])-[n;H0;D3;+0:7](:[#7;a:8]:[c:9]):[c:5](=[O;D1;H0:4]):[c:6] | 34 | [{"value": 34.0, "product": "C(C)OC(=O)C=1C=C2C(N(N=C(C2=CC1)Br)C(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.9, "product": "C(C)OC(=O)C=1C=C2C(N(N=C(C2=CC1)Br)C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 1-bromo-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester (6 g, 0.02 mol) was dissolved in DMF (60 ml). To this was added NaH (60%, 0.97 g, 0.024 mol) as a DMF suspension (5 ml). The mixture was stirred at RT for 30 min then 2-bromo-propanol (3.7 g, 0.03 mol) was added in one portion as a solution in DMF (5 m... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary alcohol | null | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | c1ccc2cnncc2c1 | HBr | CN(C)C=O | null | 0.5 | CC(Br)CO.CCOC(=O)c1ccc2c(Br)n[nH]c(=O)c2c1>CN(C)C=O>CCOC(=O)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5dbfc16dfc15488b9359043baca91a64 | CCOC(=O)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1>>CC(C)n1nc(Br)c2ccc(CO)cc2c1=O | [NH4+].[Cl-].[Li+].[BH4-].C(C)OC(=O)C=1C=C2C(N(N=C(C2=CC1)Br)C(C)C)=O.[Li+].[BH4-]>>BrC1=NN(C(C2=CC(=CC=C12)CO)=O)C(C)C | CCO[C:12]([c:11]1[cH:10][cH:9][c:8]2[c:6]([Br:7])[n:5][n:4]([CH:2]([CH3:1])[CH3:3])[c:16](=[O:17])[c:15]2[cH:14]1)=[O:13]>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([CH2:12][OH:13])[cH:14][c:15]2[c:16]1=[O:17] | CCOC(=O)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | CC(C)n1nc(Br)c2ccc(CO)cc2c1=O | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=c1[nH]ncc2ccccc12 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 44.5 | [{"value": 43.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)CO)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.5, "product": "BrC1=NN(C(C2=CC(=CC=C12)CO)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 24 | HOUR | 1-Bromo-3-isopropyl-4-oxo-3,4-dihydro-phthalazine-6-carboxylic acid ethyl ester (2.3 g, 6.8 mmol) was suspended in THF (50 ml) and cooled to 0° C. To the suspension was added LiBH4 (5.1 ml of a 2M solution in THF, 10.2 mmol) dropwise, the suspension was allowed to warm to RT and stirred for 24 hours. After this time, L... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2cnncc2c1 | HO- | C1CCOC1 | 0 | 24 | CCOC(=O)c1ccc2c(Br)nn(C(C)C)c(=O)c2c1>C1CCOC1>CC(C)n1nc(Br)c2ccc(CO)cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24d64ee3ce7b4da4be1bcda3a6f9ac68 | CC(C)n1nc(Br)c2ccc(CO)cc2c1=O.[Br-]>>CC(C)n1nc(Br)c2ccc(CBr)cc2c1=O | BrC1=NN(C(C2=CC(=CC=C12)CO)=O)C(C)C.C[Si](C)(C)Br.[Li+].[Br-]>>BrC1=NN(C(C2=CC(=CC=C12)CBr)=O)C(C)C | O[CH2:12][c:11]1[cH:10][cH:9][c:8]2[c:6]([Br:7])[n:5][n:4]([CH:2]([CH3:1])[CH3:3])[c:16](=[O:17])[c:15]2[cH:14]1.[Br-:13]>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([CH2:12][Br:13])[cH:14][c:15]2[c:16]1=[O:17] | CC(C)n1nc(Br)c2ccc(CO)cc2c1=O.[Br-] | CC(C)n1nc(Br)c2ccc(CBr)cc2c1=O | null | null | CC#N | Functional Group Interconversion | OtherReaction | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | O=c1[nH]ncc2ccccc12 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[Br-;H0;D0:5]>>[Br;H0;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 44.4 | [{"value": 44.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)CBr)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.4, "product": "BrC1=NN(C(C2=CC(=CC=C12)CBr)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A solution of 4-bromo-7-hydroxymethyl-2-isopropyl-2H-phthalazin-1-one (0.74 g, 2.5 mmol) in MeCN (5 ml) was added dropwise to a stirred suspension of TMSBr (0.9 g, 6.3 mmol) and LiBr (0.41 g, 5 mmol) in MeCN (15 ml). The reaction mixture was heated to 80° C. for 24 h, after which time the reaction mixture was cooled to... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccc2cnncc2c1 | HO- | CC#N | 80 | null | CC(C)n1nc(Br)c2ccc(CO)cc2c1=O.[Br-]>CC#N>CC(C)n1nc(Br)c2ccc(CBr)cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb4446fd96b64ba993f7f75bb602bcb5 | CC(C)n1nc(Br)c2ccc(CBr)cc2c1=O.OCC1CC1>>CC(C)n1nc(Br)c2ccc(COCC3CC3)cc2c1=O | BrC1=NN(C(C2=CC(=CC=C12)CBr)=O)C(C)C.C1(CC1)CO.[H-].[Na+]>>BrC1=NN(C(C2=CC(=CC=C12)COCC1CC1)=O)C(C)C | Br[CH2:12][c:11]1[cH:10][cH:9][c:8]2[c:6]([Br:7])[n:5][n:4]([CH:2]([CH3:1])[CH3:3])[c:20](=[O:21])[c:19]2[cH:18]1.[OH:13][CH2:14][CH:15]1[CH2:16][CH2:17]1>>[CH3:1][CH:2]([CH3:3])[n:4]1[n:5][c:6]([Br:7])[c:8]2[cH:9][cH:10][c:11]([CH2:12][O:13][CH2:14][CH:15]3[CH2:16][CH2:17]3)[cH:18][c:19]2[c:20]1=[O:21] | CC(C)n1nc(Br)c2ccc(CBr)cc2c1=O.OCC1CC1 | CC(C)n1nc(Br)c2ccc(COCC3CC3)cc2c1=O | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | O=c1[nH]ncc2ccc(COCC3CC3)cc12 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 87 | [{"value": 87.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)COCC1CC1)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.4, "product": "BrC1=NN(C(C2=CC(=CC=C12)COCC1CC1)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | Cyclopropyl-methanol (0.05 ml, 0.67 mmol) was dissolved in THF (1 ml). To this was added NaH (60%, 0.028 g, 0.72 mmol) in a single portion. The mixture was stirred at RT for 5 min then 4-bromo-7-bromomethyl-2-isopropyl-2H-phthalazin-1-one (0.2 g, 0.56 mmol) in THF (1 ml) was added in one portion and the reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccc2cnncc2c1.C1CC1 | HBr | C1CCOC1 | null | 0.083333 | CC(C)n1nc(Br)c2ccc(CBr)cc2c1=O.OCC1CC1>C1CCOC1>CC(C)n1nc(Br)c2ccc(COCC3CC3)cc2c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-84790ff519744daea89f8d0679fadac8 | CC(C)n1nc(Br)c2ccc(CBr)cc2c1=O.C[S-]>>CSCc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | C[S-].[Na+].BrC1=NN(C(C2=CC(=CC=C12)CBr)=O)C(C)C>>BrC1=NN(C(C2=CC(=CC=C12)CSC)=O)C(C)C | Br[CH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([Br:9])[n:10][n:11]([CH:12]([CH3:13])[CH3:14])[c:15](=[O:16])[c:17]2[cH:18]1.[CH3:1][S-:2]>>[CH3:1][S:2][CH2:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([Br:9])[n:10][n:11]([CH:12]([CH3:13])[CH3:14])[c:15](=[O:16])[c:17]2[cH:18]1 | CC(C)n1nc(Br)c2ccc(CBr)cc2c1=O.C[S-] | CSCc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 4f905981579db6f2866cc0ae1b975a1e274bbb1d618959665eb6b8e4dd6684b9 | e26f642c2dc9d150597dcc73347fb476ddd5d717501944aafd09c0558413a369 | O=c1[nH]ncc2ccccc12 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[S-;H0;D1:6]>>[C;D1;H3:5]-[S;H0;D2;+0:6]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 79.8 | [{"value": 79.0, "product": "BrC1=NN(C(C2=CC(=CC=C12)CSC)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.8, "product": "BrC1=NN(C(C2=CC(=CC=C12)CSC)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Sodium methanethiolate (0.23 g, 3.33 mmol) was dissolved in THF (1 ml) and added dropwise to a solution of 4-bromo-7-bromomethyl-2-isopropyl-2H-phthalazin-1-one (0.4 g, 1.11 mmol) in THF (10 ml). The mixture was stirred at RT for 3 hours whereupon LC-MS indicated complete consumption of starting material. The reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Monosulfide | null | null | c1ccc2cnncc2c1 | Br- | C1CCOC1 | null | 3 | CC(C)n1nc(Br)c2ccc(CBr)cc2c1=O.C[S-]>C1CCOC1>CSCc1ccc2c(Br)nn(C(C)C)c(=O)c2c1 |
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