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-b6144c65f26f4ab9b05a510cb7e2755e | BrBr.O=[N+]([O-])c1ncccc1O>>O=[N+]([O-])c1nc(Br)ccc1O | OC=1C(=NC=CC1)[N+](=O)[O-].C[O-].[Na+].BrBr>>BrC1=NC(=C(C=C1)O)[N+](=O)[O-] | Br[Br:7].[O:1]=[N+:2]([O-:3])[c:4]1[n:5][cH:6][cH:8][cH:9][c:10]1[OH:11]>>[O:1]=[N+:2]([O-:3])[c:4]1[n:5][c:6]([Br:7])[cH:8][cH:9][c:10]1[OH:11] | BrBr.O=[N+]([O-])c1ncccc1O | O=[N+]([O-])c1nc(Br)ccc1O | null | null | CO | Functional Group Interconversion | Bromination | 66a492ff31bfcbb52d9a760416ba269a4cf5a439a6c2ca9c2c3a3ed0a750b974 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccncc1 | Br-[Br;H0;D1;+0:1].[c:2]:[#7;a:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[#7;a:3]:[c:2]):[c:5]:[c:6] | 97.9 | [{"value": 96.0, "product": "BrC1=NC(=C(C=C1)O)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.9, "product": "BrC1=NC(=C(C=C1)O)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | 3-Hydroxy-2-nitropyridine (20 g, 0.143 mole) was dissolved in methanol (400 ml) and a solution of 25% sodium methoxide in methanol (33 ml, 0.13 mol) was added at room temperature. The mixture was stirred for 30 minutes, then cooled to 0° C., and bromine (7.2 ml, 0.14 mol) was added slowly. The reaction was then stirred... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | CO | 0 | 0.5 | BrBr.O=[N+]([O-])c1ncccc1O>CO>O=[N+]([O-])c1nc(Br)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1771243a14b444e290dbf8af8b46e80b | CCOCC.O=[N+]([O-])c1nc(Br)ccc1O>>CCOC(=O)COc1ccc(Br)nc1[N+](=O)[O-] | BrC1=NC(=C(C=C1)O)[N+](=O)[O-].C([O-])([O-])=O.[K+].[K+].CCOCC>>BrC1=CC=C(C(=N1)[N+](=O)[O-])OCC(=O)OCC | C(O[CH2:2][CH3:1])[CH3:6].[OH:7][c:8]1[cH:9][cH:10][c:11]([Br:12])[n:13][c:14]1[N+:15](=[O:16])[O-:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([Br:12])[n:13][c:14]1[N+:15](=[O:16])[O-:17] | CCOCC.O=[N+]([O-])c1nc(Br)ccc1O | CCOC(=O)COc1ccc(Br)nc1[N+](=O)[O-] | null | BrCC(=O)OCC | CC(=O)C | Acylation | OtherReaction | 93235095ed013a545ed42057f29dfe7f5561f72d80c5f9ee196c3c3abbd5e217 | e631da849ef77beac2d347b14b0af45e91e172bce5709654eb3b64211e5e4963 | c1ccncc1 | [#7;+:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[OH;D1;+0:6]):[c:7].[C;D1;H3:8]-[CH2;D2;+0:9]-O-C-[CH3;D1;+0:10]>>[#7;+:1]-[c:2](:[#7;a:3]:[c:4]):[c:5](-[O;H0;D2;+0:6]-[CH2;D2;+0:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[CH2;D2;+0:9]-[C;D1;H3:8]):[c:7] | 89 | [{"value": 89.0, "product": "BrC1=CC=C(C(=N1)[N+](=O)[O-])OCC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The hydroxypyridine (f) (30 g, 0.14 mol) was suspended in acetone (200 ml), and potassium carbonate (39 g, 0.28 mol) was added, followed by ethyl bromoacetate (15.7 ml, 0.14 mmol). The reaction was heated at reflux for 10 hours, then was cooled to room temperature and diluted with Et2O. The precipitate was removed by s... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Aromatic alcohol | Ester.Ether | null | null | c1ccncc1 | HO- | BrCC(=O)OCC.CC(=O)C | null | null | CCOCC.O=[N+]([O-])c1nc(Br)ccc1O>BrCC(=O)OCC.CC(=O)C>CCOC(=O)COc1ccc(Br)nc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-62eb967c72434b2d84f262d2fa92c337 | O=C1COc2ccc(Br)nc2N1.OB(O)/C=C/c1ccccc1>>O=C1COc2ccc(/C=C/c3ccccc3)nc2N1 | BrC=1C=CC=2OCC(NC2N1)=O.C1(=CC=CC=C1)/C=C/B(O)O.C([O-])([O-])=O.[K+].[K+]>>C(=C\C1=CC=CC=C1)/C=1C=CC=2OCC(NC2N1)=O | Br[c:8]1[cH:7][cH:6][c:5]2[c:18]([n:17]1)[NH:19][C:2](=[O:1])[CH2:3][O:4]2.OB(O)/[CH:9]=[CH:10]/[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6][cH:7][c:8](/[CH:9]=[CH:10]/[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:17][c:18]2[NH:19]1 | O=C1COc2ccc(Br)nc2N1.OB(O)/C=C/c1ccccc1 | O=C1COc2ccc(/C=C/c3ccccc3)nc2N1 | 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 | O1CCOCC1.O.CCOC(=O)C | C-C Coupling | Suzuki coupling with boronic acids | 78d8ad3441f90b689fe1e4594cfb21db4fe84d29bf0173beafcec322882a7de6 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C1COc2ccc(/C=C/c3ccccc3)nc2N1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[c:5]:[c:6].O-B(-O)/[CH;D2;+0:7]=[C:8]/[c:9](:[c:10]):[c:11]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](/[CH;D2;+0:7]=[C:8]/[c:9](:[c:10]):[c:11]):[c:5]:[c:6] | 38 | [{"value": 38.0, "product": "C(=C\\C1=CC=CC=C1)/C=1C=CC=2OCC(NC2N1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.7, "product": "C(=C\\C1=CC=CC=C1)/C=1C=CC=2OCC(NC2N1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The bromopyridine (h) (6.0 g, 26.3 mmol) and trans-2-phenylvinylboronic acid (3.9 g, 26.3 mmol) were dissolved in 1,4-dioxane (150 ml) and the solution was degassed with argon. (Ph3P)4Pd (230 mg, 0.2 mmol) was added, followed by a solution of potassium carbonate (6.9 g, 50 mmol) in water (20 ml). The reaction was heate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cnc2c(c1)OCCN2 | c1cnc2c(c1)OCCN2 | c1cnc2c(c1)OCCN2.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.O.CCOC(=O)C | null | null | O=C1COc2ccc(Br)nc2N1.OB(O)/C=C/c1ccccc1>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.O1CCOCC1.O.CCOC(=O)C>O=C1COc2ccc(/C=C/c3ccccc3)nc2N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa7e0147be2e4f0db41ecde21e4aadae | C[O-].Clc1ccc2cccc(OCc3ccccc3)c2n1>>COc1ccc2cccc(OCc3ccccc3)c2n1 | ClC1=NC2=C(C=CC=C2C=C1)OCC1=CC=CC=C1.C[O-].[Na+]>>C(C1=CC=CC=C1)OC=1C=CC=C2C=CC(=NC12)OC | [CH3:1][O-:2].Cl[c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[c:19]2[n:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[c:19]2[n:20]1 | C[O-].Clc1ccc2cccc(OCc3ccccc3)c2n1 | COc1ccc2cccc(OCc3ccccc3)c2n1 | null | null | C1(=CC=CC=C1)C.CO | Heteroatom Alkylation and Arylation | OtherReaction | dd6932defb2e2d09070bf47b6101415c37de430a4951062bc340a73ed05c28e0 | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1ccc(COc2cccc3cccnc23)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[O-;H0;D1:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 92 | [{"value": 92.0, "product": "C(C1=CC=CC=C1)OC=1C=CC=C2C=CC(=NC12)OC", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 8 | HOUR | The crude 2-chloro-8-benzyloxyquinoline from above was dissolved in toluene (10 mL) and added to a stirred 25 wt % solution of NaOMe in MeOH (50 mL). The reaction solution was heated with stirring overnight at 70° C. After cooling to room temperature, the reaction solution was poured onto ice and extracted with toluene... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | Other | C1(=CC=CC=C1)C.CO | 70 | 8 | C[O-].Clc1ccc2cccc(OCc3ccccc3)c2n1>C1(=CC=CC=C1)C.CO>COc1ccc2cccc(OCc3ccccc3)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-22eb2861c23d43d680bdd14f2f88c5d2 | CC(C)(C)OC(=O)N1CC[C@H](NCc2ccccc2)[C@H](F)C1>>CC(C)(C)OC(=O)N1CC[C@@H](N)[C@@H](F)C1 | C(C1=CC=CC=C1)N[C@@H]1[C@@H](CN(CC1)C(=O)OC(C)(C)C)F.Cl>>N[C@H]1[C@H](CN(CC1)C(=O)OC(C)(C)C)F | c1ccc(C[NH:12][C@H:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:15][C@H:13]2[F:14])cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]([NH2:12])[C@@H:13]([F:14])[CH2:15]1 | CC(C)(C)OC(=O)N1CC[C@H](NCc2ccccc2)[C@H](F)C1 | CC(C)(C)OC(=O)N1CC[C@@H](N)[C@@H](F)C1 | null | [Pd] | CCO | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | C1CCNCC1 | [C:1]-[C:2](-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1)-[C:4]>>[C:1]-[C:2](-[NH2;D1;+0:3])-[C:4] | 53 | [{"value": 53.0, "product": "N[C@H]1[C@H](CN(CC1)C(=O)OC(C)(C)C)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of the enantiomeric mixture of cis-4-benzylamino-1-tert-butoxycarbonyl-3-fluoropiperidine (prepared according to the procedures of J. Med. Chem. 1999, 42, 2087-2104, 1.0 g, 3.2 mmole) in EtOH (40 mL) was added 3 N HCl (2.5 L) and 10% Pd/C (50 mg). The reaction was shaken under H2 (40 psi) on a Parr appara... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | C1CC[NH]CC1 | Other | [Pd].CCO | null | 14 | CC(C)(C)OC(=O)N1CC[C@H](NCc2ccccc2)[C@H](F)C1>[Pd].CCO>CC(C)(C)OC(=O)N1CC[C@@H](N)[C@@H](F)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ccf3fbfdecfa45b4b7a9b1ffc953c189 | CCOC(=O)CS.COC(=O)c1ccc(Br)c(N)n1>>COC(=O)c1ccc2c(n1)NC(=O)CS2 | SCC(=O)OCC.[H-].[Na+].NC1=C(C=CC(=N1)C(=O)OC)Br>>O=C1NC2=C(SC1)C=CC(=N2)C(=O)OC | CCO[C:12](=[O:13])[CH2:14][SH:15].Br[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[n:10][c:9]1[NH2:11]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([n:10]1)[NH:11][C:12](=[O:13])[CH2:14][S:15]2 | CCOC(=O)CS.COC(=O)c1ccc(Br)c(N)n1 | COC(=O)c1ccc2c(n1)NC(=O)CS2 | null | null | CN(C)C=O.CCOC(=O)C | Acylation | OtherReaction | fd7342aebd388ea0258590b8154abb6692348e465fe66bbcd1afc68573c01546 | 998b836dac7df9ef4e0c29fab0a2e58509223c9eecb587a6e49e6cb1927e3269 | O=C1CSc2cccnc2N1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[C:5](-[#8:6])=[O;D1;H0:7]):[#7;a:8]:[c:9]:1-[NH2;D1;+0:10].C-C-O-[C;H0;D3;+0:11](=[O;D1;H0:12])-[C:13]-[SH;D1;+0:14]>>[#8:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[#7;a:8]:[c:9]2:[c;H0;D3;+0:1](:[c:2]:[c:3]:1)-[S;H0;D2;+0:14]-[C:13]-[C;H0;D3;+0:11](=[O;D1;H0:12])-[NH;D2;+0:10]-2 | null | [] | null | null | 16 | HOUR | A solution of ethyl 2-mercaptoacetate (1.473 ml) in DMF (48 ml) was ice-cooled and treated with sodium hydride (540 mg of a 60% dispersion in oil). After 1 hour methyl 6-amino-5-bromopyridine-2-carboxylate (3 g) (T. R. Kelly and F. Lang, J. Org. Chem. 61, 1996, 4623-4633) was added and the mixture stirred for 16 hours ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Primary amine.Aliphatic thiol | Secondary amide.Monosulfide | c1ccncc1 | c1cnc2c(c1)SCCN2 | c1cnc2c(c1)SCCN2 | HBr | CN(C)C=O.CCOC(=O)C | null | 16 | CCOC(=O)CS.COC(=O)c1ccc(Br)c(N)n1>CN(C)C=O.CCOC(=O)C>COC(=O)c1ccc2c(n1)NC(=O)CS2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5389309b1db84247bd8965dc569dee38 | Nc1ccc2c(c1)OCCO2.O=C1CCC(=O)N1Br>>Nc1cc2c(cc1Br)OCCO2 | O1CCOC2=C1C=CC(=C2)N.BrN1C(CCC1=O)=O>>BrC=1C(=CC2=C(OCCO2)C1)N | [NH2:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][cH:7]1)[O:9][CH2:10][CH2:11][O:12]2.O=C1CCC(=O)N1[Br:8]>>[NH2:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[Br:8])[O:9][CH2:10][CH2:11][O:12]2 | Nc1ccc2c(c1)OCCO2.O=C1CCC(=O)N1Br | Nc1cc2c(cc1Br)OCCO2 | null | S(O)(O)(=O)=O | O1CCCC1 | Functional Group Interconversion | Bromination | a683c5962e98910595430760c059b8fbd3e5a3a01d899cb18c746d382c82d9f0 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc2c(c1)OCCO2 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8:2]-[c:3]:[c:4]:[cH;D2;+0:5]:[c:6](-[N;D1;H2:7]):[c:8]>>[#8:2]-[c:3]:[c:4]:[c;H0;D3;+0:5](-[Br;H0;D1;+0:1]):[c:6](-[N;D1;H2:7]):[c:8] | 93 | [{"value": 93.0, "product": "BrC=1C(=CC2=C(OCCO2)C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.2, "product": "BrC=1C(=CC2=C(OCCO2)C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,3-dihydro-benzo[1,4]dioxin-6-ylamine (1 g, 6.6 mmol) in tetrahydrofuran (15 ml) was cooled to −78 deg C. then treated with 1 drop of concentrated sulphuric acid followed by N-bromosuccinimide (1.2 g, 6.6 mmol). The mixture was allowed to warm to room temperature over 1 hour then evaporated. The residue ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccc2c(c1)OCCO2.C1CCNC1 | c1ccc2c(c1)OCCO2 | c1ccc2c(c1)OCCO2 | HO- | S(O)(O)(=O)=O.O1CCCC1 | null | null | Nc1ccc2c(c1)OCCO2.O=C1CCC(=O)N1Br>S(O)(O)(=O)=O.O1CCCC1>Nc1cc2c(cc1Br)OCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-921de28713984b36864e4ef621b2a860 | BrP(Br)Br.CN(C)C=O.O=c1ccc2ccccc2[nH]1>>Brc1ccnc2ccc3c(c12)OCCO3 | N1C(C=CC2=CC=CC=C12)=O.CN(C)C=O.P(Br)(Br)Br.C([O-])([O-])=O.[Na+].[Na+]>>BrC1=CC=NC2=CC=C3C(=C12)OCCO3 | BrP(Br)[Br:1].CN([CH3:13])[CH:14]=[O:15].O=[c:4]1[cH:3][cH:2][c:11]2[c:6]([nH:5]1)[cH:7][cH:8][cH:9][cH:10]2>>[Br:1][c:2]1[cH:3][cH:4][n:5][c:6]2[cH:7][cH:8][c:9]3[c:10]([c:11]12)[O:12][CH2:13][CH2:14][O:15]3 | BrP(Br)Br.CN(C)C=O.O=c1ccc2ccccc2[nH]1 | Brc1ccnc2ccc3c(c12)OCCO3 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a884ada1d83074db56440d3d8c610de7c4a9b0d902fc0d7423cd90106971a138 | d96acf91751850980fec5b70a04aae6e61f0a8ec112a6f241542bec65b10b883 | c1cnc2ccc3c(c2c1)OCCO3 | Br-P(-Br)-[Br;H0;D1;+0:1].C-N(-[CH3;D1;+0:2])-[CH;D2;+0:3]=[O;H0;D1;+0:4].O=[c;H0;D3;+0:5]1:[c:6]:[cH;D2;+0:7]:[c:8]2:[cH;D2;+0:9]:[cH;D2;+0:10]:[c:11]:[c:12]:[c:13]:2:[nH;D2;+0:14]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:7]1:[c:6]:[cH;D2;+0:5]:[n;H0;D2;+0:14]:[c:13]2:[c:12]:[c:11]:[c;H0;D3;+0:10]3:[c;H0;D3;+0:9](:[c:8]:2:1)-[#... | null | [] | null | null | null | null | The quinolinone (4d) in dry DMF (8 mL) was cooled in ice and phosphorus tribromide (0.7 mL) added drop-wise, and the mixture was stirred, with ice-cooling for 30 minutes then allowed to warm to room temperature and stirred for a further 2 hours. It was cooled in ice and sodium carbonate solution was added and the solid... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aromatic halide.Ether.Ether | c1ccc2ccccc2n1 | c1cnc2ccc3c(c2c1)OCCO3 | c1cnc2ccc3c(c2c1)OCCO3 | HBr | null | null | null | BrP(Br)Br.CN(C)C=O.O=c1ccc2ccccc2[nH]1>>Brc1ccnc2ccc3c(c12)OCCO3 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1340d3bd4404429894d76f1b31fee918 | CC(C)[Si](Cl)(C(C)C)C(C)C.Nc1c(O)cccc1[N+](=O)[O-]>>CC(C)[Si](Oc1cccc([N+](=O)[O-])c1N)(C(C)C)C(C)C | NC1=C(C=CC=C1[N+](=O)[O-])O.N1C=NC=C1.Cl[Si](C(C)C)(C(C)C)C(C)C>>[N+](=O)([O-])C1=C(C(=CC=C1)O[Si](C(C)C)(C(C)C)C(C)C)N | Cl[Si:4]([CH:2]([CH3:1])[CH3:3])([CH:16]([CH3:17])[CH3:18])[CH:19]([CH3:20])[CH3:21].[OH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[c:14]1[NH2:15]>>[CH3:1][CH:2]([CH3:3])[Si:4]([O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[c:14]1[NH2:15])([CH:16]([CH3:17])[CH3:18])[CH:19]([CH3:20])[CH3:21] | CC(C)[Si](Cl)(C(C)C)C(C)C.Nc1c(O)cccc1[N+](=O)[O-] | CC(C)[Si](Oc1cccc([N+](=O)[O-])c1N)(C(C)C)C(C)C | null | null | O1CCCC1 | Protection | Alcohol protection with silyl ethers | b0a79881d208ba0e98fadf827b99c8e154abae20183442d92687b20dcffdaf4c | d57b05ecffa00e68e6b49fce42d0b589b6267b94f85326e13293a0e3abd8a48b | c1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](-[C;D1;H3:9])-[C;D1;H3:10].[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])-[Si;H0;D4;+0:1](-[O;H0;D2;+0:11]-[c:12](:[c:13]):[c:14])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](-[C;D1;H3:9])-[C;D1;H3:10] | 105.4 | [{"value": 105.4, "product": "[N+](=O)([O-])C1=C(C(=CC=C1)O[Si](C(C)C)(C(C)C)C(C)C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-amino-3-nitro-phenol (42.9 g, 278 mmol) and imidazole (28.4 g, 417 mmol) in tetrahydrofuran (750 ml) was treated with chloro-triisopropyl-silane (62.3 g, 323 mmol). After 18 hours the mixture was filtered, diluted with ethyl acetate, washed with water, dried and evaporated to give an oil (91 g).
Conditi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | Silyl protective group | null | null | c1ccccc1 | HCl | O1CCCC1 | null | null | CC(C)[Si](Cl)(C(C)C)C(C)C.Nc1c(O)cccc1[N+](=O)[O-]>O1CCCC1>CC(C)[Si](Oc1cccc([N+](=O)[O-])c1N)(C(C)C)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cc3e14f7f9fe48f6a3d9e72cd7594f8e | N.O=c1cc(CO)occ1OCc1ccccc1>>O=c1cc(CO)[nH]cc1OCc1ccccc1 | C(C1=CC=CC=C1)OC=1C(C=C(OC1)CO)=O.C1=C(OC=C(C1=O)O)CO.N.COC1=CC=CC=C1OC(CO)C(C2=CC(=C(C=C2)O)OC)O>>C(C1=CC=CC=C1)OC=1C(C=C(NC1)CO)=O | [NH3:7].o1[c:4]([CH2:5][OH:6])[cH:3][c:2](=[O:1])[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:8]1>>[O:1]=[c:2]1[cH:3][c:4]([CH2:5][OH:6])[nH:7][cH:8][c:9]1[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | N.O=c1cc(CO)occ1OCc1ccccc1 | O=c1cc(CO)[nH]cc1OCc1ccccc1 | null | null | C(C)O | Miscellaneous | OtherReaction | a770a0f1322d1d6fc09ae7bc719fc50a835416dcc33e1a46a0f3709d69d63210 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=c1cc[nH]cc1OCc1ccccc1 | [#8:1]-[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[C:6]-[O;D1;H1:7]):o:[cH;D2;+0:8]:1.[NH3;D0;+0:9]>>[#8:1]-[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[C:6]-[O;D1;H1:7]):[nH;D2;+0:9]:[cH;D2;+0:8]:1 | null | [] | null | null | null | null | A mixture of 5-benzyloxy-2-hydroxymethyl-4-pyrone (prepared from Kojic acid by the method of D. Erol, J. Med. Chem., 1994, 29, 893) (9.7 g, 40 mmol), concentrated aqueous (880) ammonia (100 mL), and ethanol (20 mL) was heated to reflux overnight. The mixture was allowed to cool to room temperature then filtered. The re... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccocc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HO- | C(C)O | null | null | N.O=c1cc(CO)occ1OCc1ccccc1>C(C)O>O=c1cc(CO)[nH]cc1OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2034badeb438445dac16877f59b9ef1e | BrP(Br)Br.CN(C)C=O.O=c1[nH]c2ccccc2cc1Cl>>Clc1cnc2ccc3c(c2c1Br)OCCO3 | ClC=1C(NC2=CC=CC=C2C1)=O.CN(C)C=O.P(Br)(Br)Br.C([O-])([O-])=O.[Na+].[Na+]>>BrC1=C(C=NC2=CC=C3C(=C12)OCCO3)Cl | BrP(Br)[Br:12].CN([CH3:14])[CH:15]=[O:16].[Cl:1][c:2]1[c:3](=[O:13])[nH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[cH:11]1>>[Cl:1][c:2]1[cH:3][n:4][c:5]2[cH:6][cH:7][c:8]3[c:9]([c:10]2[c:11]1[Br:12])[O:13][CH2:14][CH2:15][O:16]3 | BrP(Br)Br.CN(C)C=O.O=c1[nH]c2ccccc2cc1Cl | Clc1cnc2ccc3c(c2c1Br)OCCO3 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c498ab1945e046e969baffc85889dd5f9a4435d12d5e5cb25029d0a429a69d13 | d96acf91751850980fec5b70a04aae6e61f0a8ec112a6f241542bec65b10b883 | c1cnc2ccc3c(c2c1)OCCO3 | Br-P(-Br)-[Br;H0;D1;+0:1].C-N(-[CH3;D1;+0:2])-[CH;D2;+0:3]=[O;H0;D1;+0:4].[Cl;D1;H0:5]-[c:6]1:[cH;D2;+0:7]:[c:8]2:[cH;D2;+0:9]:[cH;D2;+0:10]:[c:11]:[c:12]:[c:13]:2:[nH;D2;+0:14]:[c;H0;D3;+0:15]:1=[O;H0;D1;+0:16]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:7]1:[c:8]2:[c:13](:[c:12]:[c:11]:[c;H0;D3;+0:10]3:[c;H0;D3;+0:9]:2-[O;H0;D2;+0:... | null | [] | null | null | null | null | The chloroquinolone (7a) in dry DMF (8 mL) was cooled in ice and phosphorus tribromide (0.7 mL) added drop-wise, and the mixture was stirred, with ice-cooling for 30 minutes then allowed to warm to room temperature and stirred for a further 2 hours. It was cooled in ice and sodium carbonate solution was added and the s... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aromatic halide.Ether.Ether | c1cnc2ccccc2c1 | c1cnc2ccc3c(c2c1)OCCO3 | c1cnc2ccc3c(c2c1)OCCO3 | HBr | null | null | null | BrP(Br)Br.CN(C)C=O.O=c1[nH]c2ccccc2cc1Cl>>Clc1cnc2ccc3c(c2c1Br)OCCO3 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-60614bbfc0554c2f9387e571239d1365 | CC(C)(C)OC(=O)NC1CCN(CCc2ccnc3ccccc23)CC1.ClC(Cl)Cl>>Cl.Cl.Cl.NC1CCN(CCc2ccnc3ccccc23)CC1 | N1=CC=C(C2=CC=CC=C12)CCN1CCC(CC1)NC(OC(C)(C)C)=O.C(Cl)(Cl)Cl>>Cl.Cl.Cl.N1=CC=C(C2=CC=CC=C12)CCN1CCC(CC1)N | CC(C)(C)OC(=O)[NH:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:9][CH2:10][c:11]2[cH:12][cH:13][n:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1.C([Cl:1])([Cl:2])[Cl:3]>>[ClH:1].[ClH:2].[ClH:3].[NH2:4][CH:5]1[CH2:6][CH2:7][N:8]([CH2:9][CH2:10][c:11]2[cH:12][cH:13][n:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)... | CC(C)(C)OC(=O)NC1CCN(CCc2ccnc3ccccc23)CC1.ClC(Cl)Cl | Cl.Cl.Cl.NC1CCN(CCc2ccnc3ccccc23)CC1 | null | null | Cl.O1CCOCC1 | Miscellaneous | OtherReaction | 9af4569dd9ae207ad9732ca20e1ec8fa52873c2a73ee1ffb49355c6a5b75afa5 | 31d55efd31a51120d5a13a16573aae7ab930291a25034a46043f117def7cff3c | c1ccc2c(CCN3CCCCC3)ccnc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4].[Cl;H0;D1;+0:5]-C(-[Cl;H0;D1;+0:6])-[Cl;H0;D1;+0:7]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4].[ClH;D0;+0:5].[ClH;D0;+0:6].[ClH;D0;+0:7] | 100 | [{"value": 100.0, "product": "Cl.Cl.Cl.N1=CC=C(C2=CC=CC=C12)CCN1CCC(CC1)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 1,1-dimethylethyl {1-[2-(4-quinolinyl)ethyl]-4-piperidinyl}carbamate (9a) (278 mg) was dissolved in chloroform and diluted with 4N HCl in dioxane solution. After stirring two hours, the reaction mixture was evaporated to dryness to afford the product as a solid (180 mg, 100%).
Conditions: See reaction.notes.procedure_d... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Secondary halide.Carbamic ester.Ether.Boc | Primary amine | null | null | C1CC[NH]CC1.c1ccc2ncccc2c1 | HO- | Cl.O1CCOCC1 | null | 2 | CC(C)(C)OC(=O)NC1CCN(CCc2ccnc3ccccc23)CC1.ClC(Cl)Cl>Cl.O1CCOCC1>Cl.Cl.Cl.NC1CCN(CCc2ccnc3ccccc23)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bd056aa6698646c688e0db6a8fc59919 | CC(C)(C)OC(=O)N[C@H]1CCN(C(=O)OCc2ccccc2)C[C@H]1O>>CC(C)(C)OC(=O)N[C@H]1CCNC[C@H]1O | C(C1=CC=CC=C1)OC(=O)N1C[C@H]([C@H](CC1)NC(=O)OC(C)(C)C)O>>C(C)(C)(C)OC(N[C@@H]1[C@@H](CNCC1)O)=O | O=C(OCc1ccccc1)[N:12]1[CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C@H:14]([OH:15])[CH2:13]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][NH:12][CH2:13][C@H:14]1[OH:15] | CC(C)(C)OC(=O)N[C@H]1CCN(C(=O)OCc2ccccc2)C[C@H]1O | CC(C)(C)OC(=O)N[C@H]1CCNC[C@H]1O | null | null | CO | Reduction | Hydrogenolysis of tertiary amines | ce0208fabe82d1244d7db7b6f7627b1b39a8cf3492e02720426849e93718e81c | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | C1CCNCC1 | O=C(-O-C-c1:c:c:c:c:c:1)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 100.5 | [{"value": 100.0, "product": "C(C)(C)(C)OC(N[C@@H]1[C@@H](CNCC1)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.5, "product": "C(C)(C)(C)OC(N[C@@H]1[C@@H](CNCC1)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | 10.0 g of cis-4-tert-Butoxycarbonylamino-3-hydroxy-piperidine-1-carboxylic acid benzyl ester slow running Isomer 2 (10b), was dissolved in methanol (350 mL) and was degassed. Pearlman's catalyst (palladium hydroxide on carbon, 20wt % Pd (dry basis), ≦50% water, 500 mg) was added and the mixture was purged with hydrogen... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1 | HO- | CO | null | 12 | CC(C)(C)OC(=O)N[C@H]1CCN(C(=O)OCc2ccccc2)C[C@H]1O>CO>CC(C)(C)OC(=O)N[C@H]1CCNC[C@H]1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e88a9445e8274bf7abe3c92f6eae2544 | CCOC(=O)CC(=O)C(C)C.N#CCC#N>>CCOC(=O)CC(=C(C#N)C#N)C(C)C | C(CC#N)#N.C(C)(=O)[O-].[NH4+].C(C)(=O)O.C(C(C)C)(=O)CC(=O)OCC>>C(#N)C(=C(CC(=O)OCC)C(C)C)C#N | O=[C:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:13]([CH3:14])[CH3:15].[CH2:8]([C:9]#[N:10])[C:11]#[N:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[C:8]([C:9]#[N:10])[C:11]#[N:12])[CH:13]([CH3:14])[CH3:15] | CCOC(=O)CC(=O)C(C)C.N#CCC#N | CCOC(=O)CC(=C(C#N)C#N)C(C)C | null | null | O.C1(=CC=CC=C1)C | C-C Coupling | Knoevenagel Condensation | b47050f08d82e3e68de9d69580af9026f89fe179af05d47a7df8437aa12924dc | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | null | O=[C;H0;D3;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C:7](-[C;D1;H3:8])-[C;D1;H3:9].[N;D1;H0:10]#[C:11]-[CH2;D2;+0:12]-[C:13]#[N;D1;H0:14]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C:2]-[C;H0;D3;+0:1](-[C:7](-[C;D1;H3:8])-[C;D1;H3:9])=[C;H0;D3;+0:12](-[C:13]#[N;D1;H0:14])-[C:11]#[N;D1;H0:10] | null | [] | null | null | null | null | 1.2 30 g of malononitrile, 3.3 g of ammonium acetate and 4 ml of acetic acid are added to a solution of 55 g of ethyl 2-(isobutyryl)acetate (“AA”) in 210 ml of toluene, and the mixture is boiled at 130° for 1 hour on a water separator. Conventional work-up gives 41.0 g of ethyl 4,4-di-cyano-3-isopropylbut-3-enoate (“AB... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | null | null | null | HO- | O.C1(=CC=CC=C1)C | null | null | CCOC(=O)CC(=O)C(C)C.N#CCC#N>O.C1(=CC=CC=C1)C>CCOC(=O)CC(=C(C#N)C#N)C(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-62c7a6143c584a9fa367b7bf3a5fe3c7 | CC(C)(C)OC(=O)N1CCC(=O)CC1>>CC(C)(C)OC(=O)N1CCC2(CC1)CO2 | O.CC(C)([O-])C.[K+].[I-].C[S+](=O)(C)C.O=C1CCN(CC1)C(=O)OC(C)(C)C>>O1CC12CCN(CC2)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[O:15])[CH2:12][CH2:13]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11]2([CH2:12][CH2:13]1)[CH2:14][O:15]2 | CC(C)(C)OC(=O)N1CCC(=O)CC1 | CC(C)(C)OC(=O)N1CCC2(CC1)CO2 | null | null | COCCOC | Heteroatom Alkylation and Arylation | OtherReaction | bdfeed694d8b2144eb92a8b3b3d70a45ccaea981e9f7225c925e2fa912434535 | 65a8af0997ec9f56fa44fac9e6db8d8aeec07e535d6b4d216a6180693919dc05 | C1CC2(CCN1)CO2 | [O;H0;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]-[C:4]-[#7:5]-[C:6]-[C:7]-1>>[#7:5]1-[C:6]-[C:7]-[C;H0;D4;+0:2]2(-[C:3]-[C:4]-1)-[C:8]-[O;H0;D2;+0:1]-2 | 81 | [{"value": 81.0, "product": "O1CC12CCN(CC2)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.8, "product": "O1CC12CCN(CC2)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Potassium t-butoxide (31 g) was added to a stirred suspension of trimethylsulfoxonium iodide (60.8 g) in 1,2-dimethoxyethane (250 ml) at 20° C. After 1 hour, the mixture was added portionwise over 30 minutes to a stirred solution of 4-oxo-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester (50 g) in 1,2-dimethoxyethan... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ether | C1CC[NH]CC1 | C1CC2(CC[NH]1)CO2 | C1CC2(CC[NH]1)CO2 | Other | COCCOC | null | 1 | CC(C)(C)OC(=O)N1CCC(=O)CC1>COCCOC>CC(C)(C)OC(=O)N1CCC2(CC1)CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-68adbf71b21c4ac5a649a3d1da610519 | COc1ccccc1O.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1>>COc1ccccc1O[C@H]1CO1 | O1[C@@H](C1)COS(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-].COC1=C(C=CC=C1)O.C(=O)([O-])[O-].[Cs+].[Cs+]>>COC1=C(O[C@@H]2OC2)C=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[OH:9].O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H:10]2[CH2:11][O:12]2)c1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][C@H:10]1[CH2:11][O:12]1 | COc1ccccc1O.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1 | COc1ccccc1O[C@H]1CO1 | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 90e2015c75c1aa7fb45757d0cec4851ab498e9ae8cc5d96067d701d7cedb3f04 | 6a4a37496c8fa805da52511d47e415dabfa74c75ee96853f49be12809561cdfa | c1ccc(O[C@H]2CO2)cc1 | O=[N+](-[O-])-c1:c:c:c:c(-S(=O)(=O)-O-C-[C@H;D3;+0:1]2-[#8:2]-[C:3]-2):c:1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[c:6]:[c:5](-[O;H0;D2;+0:4]-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-1):[c:7] | 85.3 | [{"value": 85.3, "product": "COC1=C(O[C@@H]2OC2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (777 mg, 3.0 mmol), 2-methoxyphenol (372.5 mg, 3.0 mmol) and Cs2CO3 (1.3 g, 4.0 mmol) in DMF was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over Na2SO4, filtered and co... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitro group.Aromatic alcohol.Sulfonate | Ether.Ether | c1ccccc1.C1CO1 | C1CO1 | c1ccccc1.C1CO1 | HO- | CN(C)C=O | null | 8 | COc1ccccc1O.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1>CN(C)C=O>COc1ccccc1O[C@H]1CO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-114f061e04114a049b83470f3a2890ef | CNC(=O)Cc1ccccc1O.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1>>CNC(=O)Cc1ccccc1OC[C@@H]1CO1 | OC1=C(C=CC=C1)CC(=O)NC.[N+](=O)([O-])C=1C=C(C=CC1)S(=O)(=O)OC[C@H]1OC1.C([O-])([O-])=O.[Cs+].[Cs+]>>CNC(CC1=C(C=CC=C1)OC[C@H]1OC1)=O | [CH3:1][NH:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12].O=[N+]([O-])c1cccc(S(=O)(=O)O[CH2:13][C@@H:14]2[CH2:15][O:16]2)c1>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[O:12][CH2:13][C@@H:14]1[CH2:15][O:16]1 | CNC(=O)Cc1ccccc1O.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1 | CNC(=O)Cc1ccccc1OC[C@@H]1CO1 | null | null | O.CN1C(CCC1)=O | Functional Group Interconversion | OtherReaction | 22667bd7d53403b8fb0e2b03e2cc7909a1ead78ba1b1129f63712994ec57cb5e | 0838e164784224d8b3203837b6896b22ff04a2d6540d985aab1ac4f48613d462 | c1ccc(OC[C@@H]2CO2)cc1 | O=[N+](-[O-])-c1:c:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4]-2):c:1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:8] | 28.9 | [{"value": 28.9, "product": "CNC(CC1=C(C=CC=C1)OC[C@H]1OC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 2-(2-hydroxyphenyl)-N-methylacetamide (1.00 g, 6.1 mmol) prepared according to a known procedure (Bernd, Peschke, Eur. J. Med. Chem., 2000, 35, 599-618), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (1.58 g, 6.1 mmol) and cesium carbonate (2.37 g, 7.3 mmol) in 1-methylpyrrolidin-2-one (15 ml) was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Aromatic alcohol.Sulfonate | Ether | c1ccccc1 | null | c1ccccc1.C1CO1 | HO- | O.CN1C(CCC1)=O | null | 8 | CNC(=O)Cc1ccccc1O.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1>O.CN1C(CCC1)=O>CNC(=O)Cc1ccccc1OC[C@@H]1CO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4d8fc751a0a4040a1047ec949143d05 | O=C(O)Cc1ccccc1O.O[C@H]1CCNC1>>O=C(Cc1ccccc1O)N1CC[C@H](O)C1 | N1C[C@H](CC1)O.OC1=C(C=CC=C1)CC(=O)O>>OC1=C(C=CC=C1)CC(=O)N1C[C@H](CC1)O | O[C:2](=[O:1])[CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[OH:10].[NH:11]1[CH2:12][CH2:13][C@H:14]([OH:15])[CH2:16]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[OH:10])[N:11]1[CH2:12][CH2:13][C@H:14]([OH:15])[CH2:16]1 | O=C(O)Cc1ccccc1O.O[C@H]1CCNC1 | O=C(Cc1ccccc1O)N1CC[C@H](O)C1 | null | null | CN(C)C=O | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | a590d96426a2fbaed42913d9daf8a16471a16de4978200f1d35a30a10009ebe7 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Cc1ccccc1)N1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C:5]1-[C:6]-[C:7]-[C:8]-[NH;D2;+0:9]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[N;H0;D3;+0:9]1-[C:5]-[C:6]-[C:7]-[C:8]-1 | 46.3 | [{"value": 46.3, "product": "OC1=C(C=CC=C1)CC(=O)N1C[C@H](CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | A mixture of (2-hydroxyphenyl)acetic acid (304 mg, 2.0 mmol) and N,N′-carbonyldiimidazole (405 mg, 2.5 mmol) in DMF (5 nL) was stirred at room temperature for 45 min. A solution of (3S)-pyrrolidin-3-ol (435 mg, 5.0 mmol) in DMF (1.5 mL) was added and the reaction mixture was stirred at room temperature overnight. The r... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HO- | CN(C)C=O | null | 0.75 | O=C(O)Cc1ccccc1O.O[C@H]1CCNC1>CN(C)C=O>O=C(Cc1ccccc1O)N1CC[C@H](O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c6bbb2234f50476c840d4ff4dd8187cf | O=C(Cc1ccccc1O)N1CC[C@H](O)C1.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1>>O=C(Cc1ccccc1OC[C@@H]1CO1)N1CC[C@H](O)C1 | O1[C@@H](C1)COS(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-].OC1=C(C=CC=C1)CC(=O)N1C[C@H](CC1)O.C(=O)([O-])[O-].[Cs+].[Cs+]>>O1[C@@H](C1)COC1=C(C=CC=C1)CC(=O)N1C[C@H](CC1)O | [O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[OH:10])[N:15]1[CH2:16][CH2:17][C@H:18]([OH:19])[CH2:20]1.O=[N+]([O-])c1cccc(S(=O)(=O)O[CH2:11][C@@H:12]2[CH2:13][O:14]2)c1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[O:10][CH2:11][C@@H:12]1[CH2:13][O:14]1)[N:15]1[CH2:16][CH2:17][C@H:18]([OH:19])[CH2:... | O=C(Cc1ccccc1O)N1CC[C@H](O)C1.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1 | O=C(Cc1ccccc1OC[C@@H]1CO1)N1CC[C@H](O)C1 | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 22667bd7d53403b8fb0e2b03e2cc7909a1ead78ba1b1129f63712994ec57cb5e | 0838e164784224d8b3203837b6896b22ff04a2d6540d985aab1ac4f48613d462 | O=C(Cc1ccccc1OC[C@@H]1CO1)N1CCCC1 | O=[N+](-[O-])-c1:c:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4]-2):c:1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:8] | 14.3 | [{"value": 14.3, "product": "O1[C@@H](C1)COC1=C(C=CC=C1)CC(=O)N1C[C@H](CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (228 mg, 0.88 mmol), (3S)-1-[(2-hydroxyphenyl)acetyl]pyrrolidin-3-ol (196 mg, 0.88 mmol) and Cs2CO3 (344 mg, 1.05 mmol) in DMF (5 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The organic lay... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Aromatic alcohol.Sulfonate | Ether | c1ccccc1 | null | c1ccccc1.C1CO1.C1CC[NH]C1 | HO- | CN(C)C=O | null | 8 | O=C(Cc1ccccc1O)N1CC[C@H](O)C1.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1>CN(C)C=O>O=C(Cc1ccccc1OC[C@@H]1CO1)N1CC[C@H](O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e72c213d05474d4890d4901341c88629 | CC(=O)OC(C)=O.COc1ccccc1CN>>CC(=O)NCc1ccccc1O | COC1=C(CN)C=CC=C1.C(C)(=O)OC(C)=O>>OC1=C(CNC(C)=O)C=CC=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].C[O:12][c:11]1[c:6]([CH2:5][NH2:4])[cH:7][cH:8][cH:9][cH:10]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12] | CC(=O)OC(C)=O.COc1ccccc1CN | CC(=O)NCc1ccccc1O | null | null | CO | Acylation | OtherReaction | a7082ad79b16f80dca94fefd65f42cddbc3c3cc388a3f69080e200a0f343b06f | b932aee8cf787372dd3cb58624c5f02988535b94a6333ae38c09dabd0bf4d6d3 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].C-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]-[C:8]-[NH2;D1;+0:9]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:9]-[C:8]-[c:7]:[c:5](-[OH;D1;+0:4]):[c:6] | 40.4 | [{"value": 40.4, "product": "OC1=C(CNC(C)=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | 2-Methoxybenzylamine (822 mg, 6.0 mmol) in methanol (10 mL) was treated with acetic anhydride (613 mg, 6.0 mmol) at room temperature for 2 h. The volatiles were removed in vacuo. The residue was dissolved in CH2Cl2, cooled to 0° C., 1M solution of BBr3 in CH2Cl2 (12 mL, 12.0 mml) was added slowly. After addition was co... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ether.Primary amine | Secondary amide.Aromatic alcohol | null | null | c1ccccc1 | HO- | CO | 0 | 8 | CC(=O)OC(C)=O.COc1ccccc1CN>CO>CC(=O)NCc1ccccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a891a99f7c7a4a67a6829b69796455f8 | CC(=O)NCc1ccccc1O.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1>>CC(=O)NCc1ccccc1OC[C@@H]1CO1 | OC1=C(CNC(C)=O)C=CC=C1.O1[C@@H](C1)COS(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-].C(=O)([O-])[O-].[Cs+].[Cs+]>>O1[C@@H](C1)COC1=C(CNC(C)=O)C=CC=C1 | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12].O=[N+]([O-])c1cccc(S(=O)(=O)O[CH2:13][C@@H:14]2[CH2:15][O:16]2)c1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[O:12][CH2:13][C@@H:14]1[CH2:15][O:16]1 | CC(=O)NCc1ccccc1O.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1 | CC(=O)NCc1ccccc1OC[C@@H]1CO1 | null | null | null | Functional Group Interconversion | OtherReaction | 22667bd7d53403b8fb0e2b03e2cc7909a1ead78ba1b1129f63712994ec57cb5e | 0838e164784224d8b3203837b6896b22ff04a2d6540d985aab1ac4f48613d462 | c1ccc(OC[C@@H]2CO2)cc1 | O=[N+](-[O-])-c1:c:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4]-2):c:1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:8] | 65.2 | [{"value": 65.2, "product": "O1[C@@H](C1)COC1=C(CNC(C)=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of N-(2-hydroxybenzyl)acetamide (382 mg, 2.31 mmol), (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (599 mg, 2.31 mmol) and Cs2CO3 (901 mg, 2.77 mmol) in DMP (5 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The organic layer was dried over N... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Aromatic alcohol.Sulfonate | Ether | c1ccccc1 | null | c1ccccc1.C1CO1 | HO- | null | null | 8 | CC(=O)NCc1ccccc1O.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1>>CC(=O)NCc1ccccc1OC[C@@H]1CO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef69b6f7495e473da852aa96bc95b40c | CN.COc1ccc(CC(=O)O)c(OC)c1>>CNC(=O)Cc1ccc(OC)cc1OC | C(C)(=O)OCC.COC1=C(C=CC(=C1)OC)CC(=O)O.C1=CN(C=N1)C(=O)N2C=CN=C2.CN>>COC1=C(C=CC(=C1)OC)CC(=O)NC | [CH3:1][NH2:2].O[C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH3:11])[cH:12][c:13]1[O:14][CH3:15]>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH3:11])[cH:12][c:13]1[O:14][CH3:15] | CN.COc1ccc(CC(=O)O)c(OC)c1 | CNC(=O)Cc1ccc(OC)cc1OC | null | null | O.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C;D1;H3:5]-[NH2;D1;+0:6]>>[C;D1;H3:5]-[NH;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | 73.3 | [{"value": 73.3, "product": "COC1=C(C=CC(=C1)OC)CC(=O)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | A mixture of (2,4-dimethoxyphenyl)acetic acid (577 mg, 3.0 mmol) and N,N-carbonyldiimidazole (608 mg, 3.75 mmol) in DMF (10 mL) was stirred at room temperature for 45 min, aqueous 40% methyl amine (4.5 mL) was added and the reaction mixture was stirred at room temperature over the week-end. The reaction mixture was is ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | O.CN(C)C=O | null | 0.75 | CN.COc1ccc(CC(=O)O)c(OC)c1>O.CN(C)C=O>CNC(=O)Cc1ccc(OC)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4df6b0a2d19445ef82ebb5c8053a5c34 | CNC(=O)Cc1ccc(OC)cc1OC.CO>>CNC(=O)Cc1ccc(O)cc1OC.CNC(=O)Cc1ccc(OC)cc1O | CO.COC1=C(C=CC(=C1)OC)CC(=O)NC.B(Br)(Br)Br>>OC1=C(C=CC(=C1)OC)CC(=O)NC.OC1=CC(=C(C=C1)CC(=O)NC)OC | [CH3:1][NH:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH3:15])[cH:11][c:12]1[O:13][CH3:14].[CH3:17][OH:18]>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:11][c:12]1[O:13][CH3:14].[CH3:15][NH:16][C:17](=[O:18])[CH2:19][c:20]1[cH:21][cH:22][c:23]([O:24][CH3:25])[cH:26][c:27]1[OH:28] | CNC(=O)Cc1ccc(OC)cc1OC.CO | CNC(=O)Cc1ccc(O)cc1OC.CNC(=O)Cc1ccc(OC)cc1O | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 74496ab60b015b44cd7c72128ad399821544f28cc7990de47702c32d5a37c44c | cd60a1d1b4f244c0fd53986563e105525cfc8b2fe02b7336bb25053cb1e3e0b8 | c1ccccc1.c1ccccc1 | [CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[CH3;D1;+0:6]-[OH;D1;+0:7]>>[CH3;D1;+0:1]-[#7:8]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[C:9]-[c:10].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 2.5 | HOUR | To a solution of 2-(2,4-dimethoxyphenyl)-N-methylacetamide (445 mg, 2.12 mmol) in CH2Cl2 (10 mL) was slowly added 1M BBr3 solution in CH2Cl2 (6.4 mL, 6.4 mmol). After addition was completed, the reaction mixture was stirred at 0° C. for 2.5 h, methanol (2 mL) was added and after 15 min the volatiles were removed in vac... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Methanol | Ether.Secondary amide.Aromatic alcohol.Aromatic alcohol | null | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | 0 | 2.5 | CNC(=O)Cc1ccc(OC)cc1OC.CO>C(Cl)Cl>CNC(=O)Cc1ccc(O)cc1OC.CNC(=O)Cc1ccc(OC)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bdf2fce010bd419281858860233fc2c2 | CNC(=O)Cc1ccc(OC)cc1O.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1>>CNC(=O)Cc1ccc(OC)cc1OC[C@@H]1CO1 | OC1=C(C=CC(=C1)OC)CC(=O)NC.[N+](=O)([O-])C=1C=C(C=CC1)S(=O)(=O)OC[C@H]1OC1.C(=O)([O-])[O-].[Cs+].[Cs+]>>COC1=CC(=C(C=C1)CC(=O)NC)OC[C@H]1OC1 | [CH3:1][NH:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH3:11])[cH:12][c:13]1[OH:14].O=[N+]([O-])c1cccc(S(=O)(=O)O[CH2:15][C@@H:16]2[CH2:17][O:18]2)c1>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH3:11])[cH:12][c:13]1[O:14][CH2:15][C@@H:16]1[CH2:17][O:18]1 | CNC(=O)Cc1ccc(OC)cc1O.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1 | CNC(=O)Cc1ccc(OC)cc1OC[C@@H]1CO1 | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 22667bd7d53403b8fb0e2b03e2cc7909a1ead78ba1b1129f63712994ec57cb5e | 0838e164784224d8b3203837b6896b22ff04a2d6540d985aab1ac4f48613d462 | c1ccc(OC[C@@H]2CO2)cc1 | O=[N+](-[O-])-c1:c:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4]-2):c:1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:8] | 94.3 | [{"value": 94.3, "product": "COC1=CC(=C(C=C1)CC(=O)NC)OC[C@H]1OC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 2-(2-hydroxy-4-methoxyphenyl)-N-methylacetamide (15 mg, 0.076 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (20 mg, 0.076 mmol) and Cs2CO3 (30 mg, 0.091 mmol) in DMF (1.5 mL) was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and H2O. The organic l... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Aromatic alcohol.Sulfonate | Ether | c1ccccc1 | null | c1ccccc1.C1CO1 | HO- | CN(C)C=O | null | 8 | CNC(=O)Cc1ccc(OC)cc1O.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1>CN(C)C=O>CNC(=O)Cc1ccc(OC)cc1OC[C@@H]1CO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ff70e2bfaed84faa9689afbb78621ac7 | COc1ccc([N+](=O)[O-])c(O)c1>>COc1ccc(NC(C)=O)c(O)c1 | [H][H].[N+](=O)([O-])C1=C(C=C(C=C1)OC)O.C1CCOC1>>OC1=C(C=CC(=C1)OC)NC(C)=O | [O-][N+:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:13][c:11]1[OH:12])=[O:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8]([CH3:9])=[O:10])[c:11]([OH:12])[cH:13]1 | COc1ccc([N+](=O)[O-])c(O)c1 | COc1ccc(NC(C)=O)c(O)c1 | null | [Pd] | null | Functional Group Interconversion | OtherReaction | 81e9c00cc56669b3382585c40a086ed7e5aaaab80bc5382ed121e4d5a293b433 | 013ea010a5fc8551154a976160b11b17bb85fae400bd37b37532ea17a3df22d8 | c1ccccc1 | [O-]-[N+;H0;D3:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[C;D1;H3:6]-[C:7](=[O;H0;D1;+0:2])-[NH;D2;+0:1]-[c:3](:[c:4]):[c:5] | 80 | [{"value": 80.0, "product": "OC1=C(C=CC(=C1)OC)NC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 2-Nitro-5-methoxyphenol (prepared from 3-methoxyphenol, R. J. Maleski, Synthetic Communications, 1993, 23, 343-348) (48.5 g, 0.287 mol) dissolved in THF (1.5 L) was hydrogenated at ambient temperature over night with 10% palladium on carbon (10 g) until 20.3 L of hydrogen was consumed. After filtration and evaporation ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Secondary amide | null | null | c1ccccc1 | null | [Pd] | 60 | null | COc1ccc([N+](=O)[O-])c(O)c1>[Pd]>COc1ccc(NC(C)=O)c(O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ec6e476ce1f4d9494af31ff61057d6f | COc1ccc(NC(C)=O)c(O)c1.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1>>COc1ccc(NC(C)=O)c(OC[C@@H]2CO2)c1 | N#N.OC1=C(C=CC(=C1)OC)NC(C)=O.[N+](=O)([O-])C=1C=C(C=CC1)S(=O)(=O)OC[C@H]1OC1.C([O-])([O-])=O.[Cs+].[Cs+]>>COC1=CC(=C(C=C1)NC(C)=O)OC[C@H]1OC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8]([CH3:9])=[O:10])[c:11]([OH:12])[cH:17]1.O=[N+]([O-])c1cccc(S(=O)(=O)O[CH2:13][C@@H:14]2[CH2:15][O:16]2)c1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8]([CH3:9])=[O:10])[c:11]([O:12][CH2:13][C@@H:14]2[CH2:15][O:16]2)[cH:17]1 | COc1ccc(NC(C)=O)c(O)c1.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1 | COc1ccc(NC(C)=O)c(OC[C@@H]2CO2)c1 | null | null | O.CN(C)C=O.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | 22667bd7d53403b8fb0e2b03e2cc7909a1ead78ba1b1129f63712994ec57cb5e | 0838e164784224d8b3203837b6896b22ff04a2d6540d985aab1ac4f48613d462 | c1ccc(OC[C@@H]2CO2)cc1 | O=[N+](-[O-])-c1:c:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4]-2):c:1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:8] | 122.2 | [{"value": 122.2, "product": "COC1=CC(=C(C=C1)NC(C)=O)OC[C@H]1OC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-(2-Hydroxy-4-methoxyphenyl)acetamide (18.12 g, 0.1 mol) and (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (25.92 g, 0.1 mol) were dissolved in dry DMF (75 mL) and stirred under nitrogen (N2) on an ice-bath. Cesium carbonate (35.8 g, 0.11 mol) was added and the stirring under N2 was continued at ambient temperature o... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Aromatic alcohol.Sulfonate | Ether | c1ccccc1 | null | c1ccccc1.C1CO1 | HO- | O.CN(C)C=O.C(C)(=O)OCC | null | null | COc1ccc(NC(C)=O)c(O)c1.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1>O.CN(C)C=O.C(C)(=O)OCC>COc1ccc(NC(C)=O)c(OC[C@@H]2CO2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-568c9d6a32e34e1fa7c3768c361c2f53 | C1CCNC1.COc1cc(C(C)(C)C)ccc1S(=O)(=O)Cl>>O=S(=O)(c1ccccc1O)N1CCCC1 | [Al+3].[Cl-].[Cl-].[Cl-].C(C)(C)(C)C1=CC(=C(C=C1)S(=O)(=O)Cl)OC.N1CCCC1>>N1(CCCC1)S(=O)(=O)C1=C(C=CC=C1)O | [NH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1.CC(C)(C)[c:7]1[cH:6][cH:5][c:4]([S:2](Cl)(=[O:1])=[O:3])[c:9]([O:10]C)[cH:8]1>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[OH:10])[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1 | C1CCNC1.COc1cc(C(C)(C)C)ccc1S(=O)(=O)Cl | O=S(=O)(c1ccccc1O)N1CCCC1 | null | null | CN(C)C=O.C=1(C(=CC=CC1)C)C | Acylation | OtherReaction | 8605744f3662cb4ab58973840d128f2a8ed018eba9c8f1edab4ee05d15b99b7e | 6412b36eb6c8e21e0b4f42463f9641dfd49e0e4c3c361b5df46599cf3df8e692 | O=S(=O)(c1ccccc1)N1CCCC1 | C-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c;H0;D3;+0:4](-C(-C)(-C)-C):[c:5]:[c:6]:[c:7]:1-[S;H0;D4;+0:8](-Cl)(=[O;D1;H0:9])=[O;D1;H0:10].[C:11]1-[C:12]-[C:13]-[C:14]-[NH;D2;+0:15]-1>>[O;D1;H0:9]=[S;H0;D4;+0:8](=[O;D1;H0:10])(-[N;H0;D3;+0:15]1-[C:11]-[C:12]-[C:13]-[C:14]-1)-[c:7]1:[c:6]:[c:5]:[cH;D2;+0:4]:[c:3]:[c:2]:1-[OH;D1;+0:1... | 53.3 | [{"value": 53.3, "product": "N1(CCCC1)S(=O)(=O)C1=C(C=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 4-tert-butyl-2-methoxybenzenesulfonyl chloride (258 mg, 0.99 mmol) in DMF (6 ml) was added pyrrolidine (70 mg, 0.99 mmol) and the solution was stirred at ambient temperature for 30 minutes, and concentrated in vacuo. The residue was dissolved in xylene (10 ml) and then added to mixture of AlCl3 (525 mg... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine.Sulfonyl halide | Aromatic alcohol.Tertiary amine | C1CCNC1.c1ccccc1 | c1ccccc1.C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HCl | CN(C)C=O.C=1(C(=CC=CC1)C)C | null | 0.5 | C1CCNC1.COc1cc(C(C)(C)C)ccc1S(=O)(=O)Cl>CN(C)C=O.C=1(C(=CC=CC1)C)C>O=S(=O)(c1ccccc1O)N1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bfba348b0a4443798a1486787f9034d3 | O=Cc1ccccc1O.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1>>O=Cc1ccccc1OC[C@@H]1CO1 | O.C(C=1C(O)=CC=CC1)=O.[N+](=O)([O-])C=1C=C(C=CC1)S(=O)(=O)OC[C@H]1OC1.C(=O)([O-])[O-].[Cs+].[Cs+]>>O1[C@@H](C1)COC1=C(C=O)C=CC=C1 | [O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[OH:9].O=[N+]([O-])c1cccc(S(=O)(=O)O[CH2:10][C@@H:11]2[CH2:12][O:13]2)c1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][C@@H:11]1[CH2:12][O:13]1 | O=Cc1ccccc1O.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1 | O=Cc1ccccc1OC[C@@H]1CO1 | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 22667bd7d53403b8fb0e2b03e2cc7909a1ead78ba1b1129f63712994ec57cb5e | 0838e164784224d8b3203837b6896b22ff04a2d6540d985aab1ac4f48613d462 | c1ccc(OC[C@@H]2CO2)cc1 | O=[N+](-[O-])-c1:c:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]2-[#8:3]-[C:4]-2):c:1.[O;D1;H0:5]=[C:6]-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[O;D1;H0:5]=[C:6]-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:10] | 114.8 | [{"value": 76.0, "product": "O1[C@@H](C1)COC1=C(C=O)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 114.8, "product": "O1[C@@H](C1)COC1=C(C=O)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Salicylaldehyde (486 mg, 3.99 mmol) and (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (900 mg, 3.47 mmol) was dissolved in DMF (5 ml) and Cs2CO3 (1.28 g, 3.94 mmol) was added. The reaction mixture stirred for 12 at room temperature. Water (100 ml) was added, and the mixture was extracted with DCM (2×50 ml). The combin... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Aromatic alcohol.Sulfonate | Ether | c1ccccc1 | null | c1ccccc1.C1CO1 | HO- | CN(C)C=O | null | null | O=Cc1ccccc1O.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1>CN(C)C=O>O=Cc1ccccc1OC[C@@H]1CO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f3955082ebdf49f99c8913127af764d7 | COC(=O)CBr.Oc1cc(O)c(Cl)cc1Cl>>COC(=O)COc1cc(O)c(Cl)cc1Cl | O.ClC1=C(C=C(O)C(=C1)Cl)O.C([O-])([O-])=O.[K+].[K+].BrCC(=O)OC>>ClC1=C(OCC(=O)OC)C=C(C(=C1)Cl)O | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][c:9]([OH:10])[c:11]([Cl:12])[cH:13][c:14]1[Cl:15]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([OH:10])[c:11]([Cl:12])[cH:13][c:14]1[Cl:15] | COC(=O)CBr.Oc1cc(O)c(Cl)cc1Cl | COC(=O)COc1cc(O)c(Cl)cc1Cl | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 23.2 | [{"value": 23.2, "product": "ClC1=C(OCC(=O)OC)C=C(C(=C1)Cl)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A mixture of 4,6-dichlororesorcinol (2 g), potassium carbonate (1.54 g) and methyl bromoacetate (1.71 g) in DMF (10 ml) was heated at 80° C. for 24 h. The resulting mixture was cooled and water (200 ml) added. Solid (bis-alkylated product) was filtered off, then the aqueous was acidified with aq. HCl, which was extract... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | CN(C)C=O | 80 | null | COC(=O)CBr.Oc1cc(O)c(Cl)cc1Cl>CN(C)C=O>COC(=O)COc1cc(O)c(Cl)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-177ff963ef76464a9e574524c23659ed | COC(=O)COc1cc(O)c(Cl)cc1Cl.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1>>COC(=O)COc1cc(OCC2CO2)c(Cl)cc1Cl | O.O1[C@@H](C1)COS(=O)(=O)C1=CC(=CC=C1)[N+](=O)[O-].ClC1=C(OCC(=O)OC)C=C(C(=C1)Cl)O.C(=O)([O-])[O-].[Cs+].[Cs+]>>COC(COC1=C(C=C(C(=C1)OCC1OC1)Cl)Cl)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([OH:10])[c:15]([Cl:16])[cH:17][c:18]1[Cl:19].O=[N+]([O-])c1cccc(S(=O)(=O)O[CH2:11][C@@H:12]2[CH2:13][O:14]2)c1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][c:9]([O:10][CH2:11][CH:12]2[CH2:13][O:14]2)[c:15]([Cl:16])[cH:17][c:18]1[Cl:19] | COC(=O)COc1cc(O)c(Cl)cc1Cl.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1 | COC(=O)COc1cc(OCC2CO2)c(Cl)cc1Cl | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 22667bd7d53403b8fb0e2b03e2cc7909a1ead78ba1b1129f63712994ec57cb5e | 0838e164784224d8b3203837b6896b22ff04a2d6540d985aab1ac4f48613d462 | c1ccc(OCC2CO2)cc1 | O=[N+](-[O-])-c1:c:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C@H;D3;+0:2]2-[#8:3]-[C:4]-2):c:1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[CH;D3;+0:2]1-[#8:3]-[C:4]-1):[c:8] | 46.4 | [{"value": 46.4, "product": "COC(COC1=C(C=C(C(=C1)OCC1OC1)Cl)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (0.4 g), methyl (2,4-dichloro-5-hydroxyphenoxy)acetate (0.39 g) and Cs2CO3 (0.58 g) in DMF (2 ml) was stirred at r.t. overnight. Water was added and (2,4-dichloro-5-oxiranylmethoxy-phenoxy)-acetic acid methyl ester (0.22 g) was isolated by filtration and dried... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Aromatic alcohol.Sulfonate | Ether | c1ccccc1 | null | c1ccccc1.C1CO1 | HO- | CN(C)C=O | null | 8 | COC(=O)COc1cc(O)c(Cl)cc1Cl.O=[N+]([O-])c1cccc(S(=O)(=O)OC[C@@H]2CO2)c1>CN(C)C=O>COC(=O)COc1cc(OCC2CO2)c(Cl)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb60650bae2546fa97103e49e3b80b1b | CC(C)(C)C(=O)OCCl.CCN1C(=O)C(C(=O)O)C(=O)c2cc(Nn3c(C)ccc3C)c(Cl)cc21>>CCN1C(=O)C(C(=O)OCOC(=O)C(C)(C)C)C(=O)c2cc(Nn3c(C)ccc3C)c(Cl)cc21 | N12CCCCCC2=NCCC1.ClC1=C(C=C2C(C(C(N(C2=C1)CC)=O)C(=O)O)=O)NN1C(=CC=C1C)C.C(C(C)(C)C)(=O)OCCl>>ClC1=C(C=C2C(C(C(N(C2=C1)CC)=O)C(=O)OCOC(C(C)(C)C)=O)=O)NN1C(=CC=C1C)C | Cl[CH2:10][O:11][C:12](=[O:13])[C:14]([CH3:15])([CH3:16])[CH3:17].[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH:6]([C:7](=[O:8])[OH:9])[C:18](=[O:19])[c:20]2[cH:21][c:22]([NH:23][n:24]3[c:25]([CH3:26])[cH:27][cH:28][c:29]3[CH3:30])[c:31]([Cl:32])[cH:33][c:34]21>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10]... | CC(C)(C)C(=O)OCCl.CCN1C(=O)C(C(=O)O)C(=O)c2cc(Nn3c(C)ccc3C)c(Cl)cc21 | CCN1C(=O)C(C(=O)OCOC(=O)C(C)(C)C)C(=O)c2cc(Nn3c(C)ccc3C)c(Cl)cc21 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | d0f2e7dd04291aff91491624f6ba09bd6ae2852adc109edeabfddd534d9ccfd8 | ebb133741743004d799d6738504ddfd5b4a53248a4f85602c0fff1c33566ad58 | O=C1CC(=O)c2cc(Nn3cccc3)ccc2N1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5].[#7:6]-[C:7](=[O;D1;H0:8])-[C:9](-[C:10](=[O;D1;H0:11])-[OH;D1;+0:12])-[C:13]=[O;D1;H0:14]>>[#7:6]-[C:7](=[O;D1;H0:8])-[C:9](-[C:10](=[O;D1;H0:11])-[O;H0;D2;+0:12]-[CH2;D2;+0:1]-[#8:2]-[C:3](-[C:4])=[O;D1;H0:5])-[C:13]=[O;D1;H0:14] | null | [] | null | null | 30 | MINUTE | 18 μl of 1,8-diazabicyclo[5.4.0]undec-7-ene were added to a solution of 21 mg of 7-chloro-6-(2,5-dimethylpyrrol-1-ylamino)-1-ethyl-4-oxo-1,4-dihydroquinolonecarboxylic acid (Example 36) in 3 ml of acetonitrile and stirred at room temperature for 30 minutes. Then 36 μl of chloromethyl pivalate were added, and reaction w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester.Ester | null | null | c1ccc2c(c1)CCC[NH]2.c1ccc[nH]1 | HCl | C(C)#N | null | 0.5 | CC(C)(C)C(=O)OCCl.CCN1C(=O)C(C(=O)O)C(=O)c2cc(Nn3c(C)ccc3C)c(Cl)cc21>C(C)#N>CCN1C(=O)C(C(=O)OCOC(=O)C(C)(C)C)C(=O)c2cc(Nn3c(C)ccc3C)c(Cl)cc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1e603eb5cd654201b6b599f477ad620a | CCN1C(=O)C(C(=O)OC)C(=O)c2cc(Br)cc(C)c21.Cc1cccnc1N>>CCN1C(=O)C(C(=O)OC)C(=O)c2cc(Nc3ncccc3C)cc(C)c21 | BrC=1C=C2C(C(C(N(C2=C(C1)C)CC)=O)C(=O)OC)=O.NC1=NC=CC=C1C.CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C(C=CC=C51)P(C6=CC=CC=C6)C7=CC=CC=C7)C.C([O-])([O-])=O.[Cs+].[Cs+]>>C(C)N1C(C(C(C2=CC(=CC(=C12)C)NC1=NC=CC=C1C)=O)C(=O)OC)=O | Br[c:15]1[cH:14][c:13]2[c:27]([c:25]([CH3:26])[cH:24]1)[N:3]([CH2:2][CH3:1])[C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH3:10])[C:11]2=[O:12].[NH2:16][c:17]1[n:18][cH:19][cH:20][cH:21][c:22]1[CH3:23]>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH3:10])[C:11](=[O:12])[c:13]2[cH:14][c:15]([NH:16][c:17]3[n:18]... | CCN1C(=O)C(C(=O)OC)C(=O)c2cc(Br)cc(C)c21.Cc1cccnc1N | CCN1C(=O)C(C(=O)OC)C(=O)c2cc(Nc3ncccc3C)cc(C)c21 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2] | O1CCOCC1.C(C)#N.O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 15b451da2ee5525bed9c0f9587f6aca3f4b560ed97efafb653fa9d150041c096 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C1CC(=O)c2cc(Nc3ccccn3)ccc2N1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[O;D1;H0:5]=[C:4]-[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]):[c:6]:[c:7] | null | [] | 80 | CELSIUS | null | null | 100 mg of methyl 6-bromo-1-ethyl-8-methyl-4-oxo-1,4-dihydroquinolone-3-carboxylate were transferred together with 40 mg of 2-amino-3-methylpyridine, 20 mg of Pd(OAc)2, 60 mg of XANTPHOS and 250 mg of cesium carbonate into a suitable reaction vessel, a protective gas atmosphere was generated with argon, and 10 ml of dio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2 | c1ccc2c(c1)CCC[NH]2.c1ccncc1 | HBr | CC(=O)[O-].CC(=O)[O-].[Pd+2].O1CCOCC1.C(C)#N.O | 80 | null | CCN1C(=O)C(C(=O)OC)C(=O)c2cc(Br)cc(C)c21.Cc1cccnc1N>CC(=O)[O-].CC(=O)[O-].[Pd+2].O1CCOCC1.C(C)#N.O>CCN1C(=O)C(C(=O)OC)C(=O)c2cc(Nc3ncccc3C)cc(C)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3c28c741a2714e57b6727b2b6fba0cab | CC#N.CCN1C(=O)C(C(=O)OC)C(=O)c2cc(Nc3ccc(OC)cc3C)cc(C)c21>>CCN1C(=O)C(C(=O)O)C(=O)c2cc(Nc3ncccc3C)cc(C)c21 | C(C)#N.[OH-].[Na+].C(C)N1C(C(C(C2=CC(=CC(=C12)C)NC1=C(C=C(C=C1)OC)C)=O)C(=O)OC)=O.C(C)#N>>C(C)N1C(C(C(C2=CC(=CC(=C12)C)NC1=NC=CC=C1C)=O)C(=O)O)=O | CC#[N:17].CO[c:19]1[cH:18]c[c:16]([NH:15][c:14]2[cH:13][c:12]3[c:26]([c:24]([CH3:25])[cH:23]2)[N:3]([CH2:2][CH3:1])[C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9]C)[C:10]3=[O:11])[c:21]([CH3:22])[cH:20]1>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[CH:6]([C:7](=[O:8])[OH:9])[C:10](=[O:11])[c:12]2[cH:13][c:14]([NH:15][c:16]3[n:17][cH:18][... | CC#N.CCN1C(=O)C(C(=O)OC)C(=O)c2cc(Nc3ccc(OC)cc3C)cc(C)c21 | CCN1C(=O)C(C(=O)O)C(=O)c2cc(Nc3ncccc3C)cc(C)c21 | null | null | O1CCOCC1.O | Miscellaneous | OtherReaction | 1ad6e5c4807ab7a25777871ab2bf9e0c2360b918ca30d0bd1cfde9e31e13dd0f | 342ae371817ff52211ae1fbd2418a1da815ec23722cf57c4273c7ac8958f460a | O=C1CC(=O)c2cc(Nc3ccccn3)ccc2N1 | C-C#[N;H0;D1;+0:1].C-O-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C;D1;H3:5]):[c;H0;D3;+0:6](-[#7:7]-[c:8]):c:[cH;D2;+0:9]:1.C-[O;H0;D2;+0:10]-[C:11](=[O;D1;H0:12])-[C:13](-[C:14]=[O;D1;H0:15])-[C:16](=[O;D1;H0:17])-[#7:18]>>[#7:18]-[C:16](=[O;D1;H0:17])-[C:13](-[C:11](=[O;D1;H0:12])-[OH;D1;+0:10])-[C:14]=[O;D1;H0:15].[C;D1;H3:5]-[... | null | [] | 60 | CELSIUS | null | null | Methyl 1-ethyl-6-(4-methoxy-2-methylphenylamino)-8-methyl-4-oxo-1,4-dihydroquinolone-3-carboxylate (30 mg) was dissolved in 5 ml of dioxane, 2.5 equivalents of a 1 N NaOH solution were added, and the mixture was heated at 60° C. for 4 h. Removal of the solvent in vacuo was followed by chromatography on an HPLC system t... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Nitrile | Carboxylic acid | c1ccccc1 | c1ccncc1 | c1ccc2c(c1)CCC[NH]2.c1ccncc1 | HO- | O1CCOCC1.O | 60 | null | CC#N.CCN1C(=O)C(C(=O)OC)C(=O)c2cc(Nc3ccc(OC)cc3C)cc(C)c21>O1CCOCC1.O>CCN1C(=O)C(C(=O)O)C(=O)c2cc(Nc3ncccc3C)cc(C)c21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c6ed65c4c5784155ae2a68b08100f3ea | OCc1ccccc1C1(O)CCN(Cc2ccccc2)CC1>>c1ccc(CN2CCC3(CC2)OCc2ccccc23)cc1 | O.C(C)N(CC)CC.C(C1=CC=CC=C1)N1CCC(CC1)(O)C1=C(C=CC=C1)CO.CS(=O)(=O)Cl>>C(C1=CC=CC=C1)N1CCC2(CC1)OCC1=C2C=CC=C1 | O[CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[C:9]1([OH:12])[CH2:8][CH2:7][N:6]([CH2:5][c:4]2[cH:3][cH:2][cH:1][cH:21][cH:20]2)[CH2:11][CH2:10]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][C:9]3([CH2:10][CH2:11]2)[O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]23)[cH:20][cH:21]1 | OCc1ccccc1C1(O)CCN(Cc2ccccc2)CC1 | c1ccc(CN2CCC3(CC2)OCc2ccccc23)cc1 | null | null | CCOC(=O)C.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | a9cbb1c5ad4320623d0b9fd3535c90035d7c5accf3a9016c4e2ca4bbd46fd0d6 | 71d6b370ca48f1d75269bb2a372b1608a88e28617e379e11884cc0e510f32096 | c1ccc(CN2CCC3(CC2)OCc2ccccc23)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[OH;D1;+0:6])(-[C:7])-[C:8]>>[C:7]-[C:5]1(-[C:8])-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-1 | 94.7 | [{"value": 94.7, "product": "C(C1=CC=CC=C1)N1CCC2(CC1)OCC1=C2C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 53 | CELSIUS | null | null | Crude 1-benzyl-4-(2-hydroxymethyl-phenyl)-piperidin-4-ol (180 g, 0.605 mol) was dissolved in THF (1000 mL). Triethylamine (176.18 mL, 1.27 mol) was added. A solution of methanesulfonyl chloride (33.03 mL, 0.424 mol) in THF (100 mL) was added slowly which caused an increase of the temperature from ambient to 53° C. The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary alcohol | Ether | null | c1ccc2c(c1)COC21CC[NH]CC1 | c1ccccc1.c1ccc2c(c1)COC21CC[NH]CC1 | HO- | CCOC(=O)C.C1CCOC1 | 53 | null | OCc1ccccc1C1(O)CCN(Cc2ccccc2)CC1>CCOC(=O)C.C1CCOC1>c1ccc(CN2CCC3(CC2)OCc2ccccc23)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-627a698f7a0c4733b85160b7c609626d | c1ccc(CN2CCC3(CC2)OCc2ccccc23)cc1>>c1ccc2c(c1)COC21CCNCC1 | C(C1=CC=CC=C1)N1CCC2(CC1)OCC1=C2C=CC=C1>>N1CCC2(CC1)OCC1=C2C=CC=C1 | c1ccc(C[N:12]2[CH2:11][CH2:10][C:9]3([c:4]4[cH:3][cH:2][cH:1][cH:6][c:5]4[CH2:7][O:8]3)[CH2:14][CH2:13]2)cc1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[CH2:7][O:8][C:9]21[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1 | c1ccc(CN2CCC3(CC2)OCc2ccccc23)cc1 | c1ccc2c(c1)COC21CCNCC1 | null | [Ni] | CCO | Deprotection | Hydrogenolysis of tertiary amines | 93b113cf8b83bf01341fe499b5dcfe5933cf395612199dca5726a9f828c0d8ac | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc2c(c1)COC21CCNCC1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | 80.6 | [{"value": 80.0, "product": "N1CCC2(CC1)OCC1=C2C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.6, "product": "N1CCC2(CC1)OCC1=C2C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 19 | HOUR | 1′-Benzyl-3H-spiro[2-benzofuran-1,4′-piperidine] (119 g, 425.9 mmol) was dissolved EtOH (1 L) under argon and treated with Raney nickel (12 g) at ambient temperature for 1 h to absorb impurities which tended to poison the catalyst. Raney nickel was filtered off and the filtrate was hydrogenated in a steel autoclave ove... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1ccc2c(c1)COC21CC[NH]CC1 | c1ccc2c(c1)COC21CCNCC1 | c1ccc2c(c1)COC21CCNCC1 | Other | [Ni].CCO | null | 19 | c1ccc(CN2CCC3(CC2)OCc2ccccc23)cc1>[Ni].CCO>c1ccc2c(c1)COC21CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd6b3608e24a4c67b34d1bea3eb3db73 | O=C(Cl)CCl.c1ccc2c(c1)COC21CCNCC1>>O=C(CCl)N1CCC2(CC1)OCc1ccccc12 | N1CCC2(CC1)OCC1=C2C=CC=C1.C(C)N(C(C)C)C(C)C.ClCC(=O)Cl>>ClCC(=O)N1CCC2(CC1)OCC1=CC=CC=C12 | Cl[C:2](=[O:1])[CH2:3][Cl:4].[NH:5]1[CH2:6][CH2:7][C:8]2([CH2:9][CH2:10]1)[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]12>>[O:1]=[C:2]([CH2:3][Cl:4])[N:5]1[CH2:6][CH2:7][C:8]2([CH2:9][CH2:10]1)[O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]12 | O=C(Cl)CCl.c1ccc2c(c1)COC21CCNCC1 | O=C(CCl)N1CCC2(CC1)OCc1ccccc12 | null | null | C1CCOC1 | Acylation | N-alkylation of secondary amines with alkyl halides | d8b06ee30a38200511b325ad0a1f6ad946e3adb0a323e2be329f03e34e247eb5 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc2c(c1)COC21CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4])-[C:8]-[C:9] | null | [] | 20 | CELSIUS | 15 | MINUTE | 3H-spiro[2-benzofuran-1,4′-piperidine] (5 g, 26 mmol) was dissolved in THF (100 mL) and cooled in ice. Then N-ethyldiisopropylamine (4.94 mL, 29 mmol) and chloroacetyl chloride (2.31 mL, 29 mmol) were added. The mixture was stirred at 20° C. for 15 min. The solid was filtered off and washed with THF. The filtrate was e... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1ccc2c(c1)COC21CCNCC1 | c1ccc2c(c1)COC21CC[NH]CC1 | c1ccc2c(c1)COC21CC[NH]CC1 | HCl | C1CCOC1 | 20 | 0.25 | O=C(Cl)CCl.c1ccc2c(c1)COC21CCNCC1>C1CCOC1>O=C(CCl)N1CCC2(CC1)OCc1ccccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bf91387b33b445feb8e3e4035c5d2fe0 | C=CCOC(=O)Cl.CCOC(=O)CNC(c1ccccc1)c1ccc(Cl)cc1>>C=CCOC(=O)N(CC(=O)OCC)C(c1ccccc1)c1ccc(Cl)cc1 | ClC(=O)OCC=C.C(C)OC(CNC(C1=CC=CC=C1)C1=CC=C(C=C1)Cl)=O.C(C)N(C(C)C)C(C)C>>C(C)OC(CN(C(C1=CC=CC=C1)C1=CC=C(C=C1)Cl)C(=O)OCC=C)=O | Cl[C:5]([O:4][CH2:3][CH:2]=[CH2:1])=[O:6].[NH:7]([CH2:8][C:9](=[O:10])[O:11][CH2:12][CH3:13])[CH:14]([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[c:21]1[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]1>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[N:7]([CH2:8][C:9](=[O:10])[O:11][CH2:12][CH3:13])[CH:14]([c:15]1[cH:16][cH:17][cH:... | C=CCOC(=O)Cl.CCOC(=O)CNC(c1ccccc1)c1ccc(Cl)cc1 | C=CCOC(=O)N(CC(=O)OCC)C(c1ccccc1)c1ccc(Cl)cc1 | null | null | C(Cl)Cl | Protection | N-alkylation of secondary amines with alkyl halides | 496a200c7c2fc7c000296e03cda40efb8e258ccaeb02fa999285bf74ddc49346 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | c1ccc(Cc2ccccc2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4]-[C:5]=[C;D1;H2:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]-[NH;D2;+0:12]-[C:13](-[c:14])-[c:15]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C:11]-[N;H0;D3;+0:12](-[C:13](-[c:14])-[c:15])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4]-[C:5]=[C;D1;H2:6] | 79.1 | [{"value": 78.0, "product": "C(C)OC(CN(C(C1=CC=CC=C1)C1=CC=C(C=C1)Cl)C(=O)OCC=C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.1, "product": "C(C)OC(CN(C(C1=CC=CC=C1)C1=CC=C(C=C1)Cl)C(=O)OCC=C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 16 | HOUR | (RS)-{[(4-Chloro-phenyl)-phenyl-methyl]-amino}-acetic acid ethyl ester (18 g, 59 mmol) was dissolved under nitrogen in DCM (1500 mL), N-ethyldiisopropylamine (12.2 mL, 71 mmol) was added, cooled in ice and treated with a solution of allyl chloroformate (6.4 mL, 71 mmol) in DCM (50 mL). Stirring at 20° C. was continued ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | null | null | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | 20 | 16 | C=CCOC(=O)Cl.CCOC(=O)CNC(c1ccccc1)c1ccc(Cl)cc1>C(Cl)Cl>C=CCOC(=O)N(CC(=O)OCC)C(c1ccccc1)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d77408e7d6e04f77944eea3ea5207b47 | C=CCOC(=O)N(CC(=O)OCC)C(c1ccccc1)c1ccc(Cl)cc1>>C=CCOC(=O)N(CC(=O)O)C(c1ccccc1)c1ccc(Cl)cc1 | C(C)OC(CN(C(C1=CC=CC=C1)C1=CC=C(C=C1)Cl)C(=O)OCC=C)=O.O.CO.O.[OH-].[Li+]>>C(C=C)OC(=O)N(C(C1=CC=CC=C1)C1=CC=C(C=C1)Cl)CC(=O)O | CC[O:11][C:9]([CH2:8][N:7]([C:5]([O:4][CH2:3][CH:2]=[CH2:1])=[O:6])[CH:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[c:19]1[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]1)=[O:10]>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[N:7]([CH2:8][C:9](=[O:10])[OH:11])[CH:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[c:19]1[cH:20]... | C=CCOC(=O)N(CC(=O)OCC)C(c1ccccc1)c1ccc(Cl)cc1 | C=CCOC(=O)N(CC(=O)O)C(c1ccccc1)c1ccc(Cl)cc1 | null | null | C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cc2ccccc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 66.4 | [{"value": 66.0, "product": "C(C=C)OC(=O)N(C(C1=CC=CC=C1)C1=CC=C(C=C1)Cl)CC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.4, "product": "C(C=C)OC(=O)N(C(C1=CC=CC=C1)C1=CC=C(C=C1)Cl)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (RS)-{Allyloxycarbonyl-[(4-chloro-phenyl)-phenyl-methyl]-amino}-acetic acid ethyl ester (18 g, 46.4 mmol) was dissolved in THF (60 mL), water (60 mL), and MeOH (60 mL) and treated with lithium hydroxide monohydrate (3.9 g, 92 mmol) at 20° C. for 2 h. The mixture was evaporated and extracted with AcOEt, 1 N HCl and 50% ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | C1CCOC1 | null | null | C=CCOC(=O)N(CC(=O)OCC)C(c1ccccc1)c1ccc(Cl)cc1>C1CCOC1>C=CCOC(=O)N(CC(=O)O)C(c1ccccc1)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-096b44d1e51a4d24bf466367fbbf57f7 | N#Cc1ccc(Cl)cc1Cl.[Br][Mg][c]1ccccc1>>NC(c1ccccc1)c1ccc(Cl)cc1Cl | C1(=CC=CC=C1)[Mg]Br.ClC1=C(C#N)C=CC(=C1)Cl.[BH4-].[Na+]>>ClC1=C(C=CC(=C1)Cl)C(C1=CC=CC=C1)N | [N:1]#[C:2][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]1[Cl:16].[Br][Mg][c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1>>[NH2:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]1[Cl:16] | N#Cc1ccc(Cl)cc1Cl.[Br][Mg][c]1ccccc1 | NC(c1ccccc1)c1ccc(Cl)cc1Cl | null | null | CO | C-C Coupling | OtherReaction | d655319334cde411fe032f0ba49fa2a7007dfa6098da1ed88d27602fe05a5368 | 630c8ef26e23743bc5a2ea48dac4001f5f1fc60f9477586da3af2aa3eb733a51 | c1ccc(Cc2ccccc2)cc1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[N;H0;D1;+0:6]#[C;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[NH2;D1;+0:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | The title compound was prepared from 2,4-dichloro benzonitrile and a) phenyl magnesium bromide b) NaBH4 in MeOH in analogy to known methods.9
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Nitrile | Primary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br-.Mg | CO | null | null | N#Cc1ccc(Cl)cc1Cl.[Br][Mg][c]1ccccc1>CO>NC(c1ccccc1)c1ccc(Cl)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-08f4ae8f84d840f4b1b84bd8b619e45d | CC(C)(C)OC(=O)N1CCC[C@H]1CI.C[Si](C)(C)OC(C#N)c1cccc(Cl)c1>>CC(C)(C)OC(=O)N1CCC[C@@H]1CC(=O)c1cccc(Cl)c1 | C(CCC)[Li].CCCCCC.ClC=1C=C(C=CC1)C(C#N)O[Si](C)(C)C.C(C)(C)(C)OC(=O)N1[C@@H](CCC1)CI.C(C)(C)NC(C)C>>C(C)(C)(C)OC(=O)N1[C@H](CCC1)CC(=O)C1=CC(=CC=C1)Cl | I[CH2:13][C@H:12]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10][CH2:11]1.C[Si](C)(C)[O:15][CH:14](C#N)[c:16]1[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]1[CH2:13][C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:19][c... | CC(C)(C)OC(=O)N1CCC[C@H]1CI.C[Si](C)(C)OC(C#N)c1cccc(Cl)c1 | CC(C)(C)OC(=O)N1CCC[C@@H]1CC(=O)c1cccc(Cl)c1 | null | null | C1CCOC1 | Acylation | OtherReaction | 2f7fd4e67eaf3a6246057d54b0da27ceec28f7d291e00643d614a8c0628e78e7 | 2311c6490617224163a02e02b413511508eebc59d4c2b62f531d149da3874318 | O=C(C[C@H]1CCCN1)c1ccccc1 | C-[Si](-C)(-C)-[O;H0;D2;+0:1]-[CH;D3;+0:2](-C#N)-[c:3](:[c:4]):[c:5].I-[CH2;D2;+0:6]-[C:7](-[C:8])-[#7:9](-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16])-[C:17]>>[C:8]-[C:7](-[CH2;D2;+0:6]-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[c:3](:[c:4]):[c:5])-[#7:9](-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]... | 31.5 | [{"value": 31.0, "product": "C(C)(C)(C)OC(=O)N1[C@H](CCC1)CC(=O)C1=CC(=CC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.5, "product": "C(C)(C)(C)OC(=O)N1[C@H](CCC1)CC(=O)C1=CC(=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | 15 | MINUTE | Diisopropylamine (764 uL, 5.4 mmol) was dissolved in THF (15 mL) under nitrogen and cooled to −70° C. Then a 1.6 M solution of butyllithium in hexane (3.4 mL, 5.4 mmol) was added and stirring at −70° C. was continued for 15 min. Then a solution of (3-chloro-phenyl)-trimethylsilanyloxy-acetonitrile (1.18 g, 4.9 mmol) in... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Nitrile.Silyl protective group | Ketone | null | null | C1CC[NH]C1.c1ccccc1 | HI | C1CCOC1 | -70 | 0.25 | CC(C)(C)OC(=O)N1CCC[C@H]1CI.C[Si](C)(C)OC(C#N)c1cccc(Cl)c1>C1CCOC1>CC(C)(C)OC(=O)N1CCC[C@@H]1CC(=O)c1cccc(Cl)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-09b1a57a01374b4bbdd4aa1797d597d4 | NC(c1ccccc1)c1ccccc1.O=C1OC2(CCN(C(=O)CCl)CC2)c2ccccc21>>O=C1OC2(CCN(C(=O)CNC(c3ccccc3)c3ccccc3)CC2)c2ccccc21 | O.ClCC(=O)N1CCC2(CC1)OC(C1=C2C=CC=C1)=O.C1(=CC=CC=C1)C(C1=CC=CC=C1)N.C(C)N(CC)CC>>C1(=CC=CC=C1)C(NCC(=O)N1CCC2(CC1)OC(C1=C2C=CC=C1)=O)C1=CC=CC=C1 | [NH2:11][CH:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.Cl[CH2:10][C:8]([N:7]1[CH2:6][CH2:5][C:4]2([O:3][C:2](=[O:1])[c:32]3[c:27]2[cH:28][cH:29][cH:30][cH:31]3)[CH2:26][CH2:25]1)=[O:9]>>[O:1]=[C:2]1[O:3][C:4]2([CH2:5][CH2:6][N:7]([C:8](=[O:9])[CH2:10][NH:11][CH:12]([c:13... | NC(c1ccccc1)c1ccccc1.O=C1OC2(CCN(C(=O)CCl)CC2)c2ccccc21 | O=C1OC2(CCN(C(=O)CNC(c3ccccc3)c3ccccc3)CC2)c2ccccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | O=C1OC2(CCN(C(=O)CNC(c3ccccc3)c3ccccc3)CC2)c2ccccc21 | Cl-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#7:4](-[C:5])-[C:6].[NH2;D1;+0:7]-[C:8](-[c:9])-[c:10]>>[C:5]-[#7:4](-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[NH;D2;+0:7]-[C:8](-[c:9])-[c:10])-[C:6] | null | [] | 25 | CELSIUS | 2.5 | DAY | 1′-(Chloroacetyl)-3H-spiro[2-benzofuran-1,4′-piperidine]-3-one (50 mg, 0.179 mmol)) and diphenylmethylamine (33 mg, 0.179 mmol) were dissolved in dry DMF (0.8 mL). Then triethylamine (0.074 mL, 0.536 mmol) was added and the reaction mixture was shaken at 25° C. for 2.5 days. Water (0.1 mL) was added and the whole mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)COC21CC[NH]CC1 | HCl | CN(C)C=O | 25 | 60 | NC(c1ccccc1)c1ccccc1.O=C1OC2(CCN(C(=O)CCl)CC2)c2ccccc21>CN(C)C=O>O=C1OC2(CCN(C(=O)CNC(c3ccccc3)c3ccccc3)CC2)c2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6cc1d263506d404fb7d6c7e0d9ac2aff | BrCCCBr.COC(=O)c1cc(Cl)cc(O)c1O>>COC(=O)c1cc(Cl)cc2c1OCCCO2 | COC(C1=C(C(=CC(=C1)Cl)O)O)=O.BrCCCBr.C(=O)([O-])[O-].[K+].[K+]>>ClC=1C=C(C2=C(OCCCO2)C1)C(=O)OC | Br[CH2:13][CH2:14][CH2:15]Br.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][c:10]([OH:16])[c:11]1[OH:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][c:10]2[c:11]1[O:12][CH2:13][CH2:14][CH2:15][O:16]2 | BrCCCBr.COC(=O)c1cc(Cl)cc(O)c1O | COC(=O)c1cc(Cl)cc2c1OCCCO2 | null | null | CC(C)=O | Heteroatom Alkylation and Arylation | OtherReaction | c1d419ba122c3b8de019e7646b88bc33cf015fa0a84461e5f233e021ae1598c1 | 3a4296ab1122b8b150c8c66756a35bcf5ed04942f87f4ab6361d5944860b5919 | c1ccc2c(c1)OCCCO2 | Br-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-Br.[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10](-[OH;D1;+0:11]):[c:12]>>[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8]1:[c:10](:[c:12])-[O;H0;D2;+0:11]-[CH2;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-1 | 94.8 | [{"value": 94.8, "product": "ClC=1C=C(C2=C(OCCCO2)C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5-chloro-2,3-dihydroxy-benzoic acid methyl ester (0.3 mol), 1,3-dibromopropane (0.42 mol) and K2CO3 (0.66 mol) in 2-propanone (500 ml) was stirred and refluxed for 20 hours, then filtered hot and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: DCM). T... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Aromatic alcohol.Aromatic alcohol | Ether.Ether | null | c1ccc2c(c1)OCCCO2 | c1ccc2c(c1)OCCCO2 | HBr | CC(C)=O | null | null | BrCCCBr.COC(=O)c1cc(Cl)cc(O)c1O>CC(C)=O>COC(=O)c1cc(Cl)cc2c1OCCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6c5f9646199d45d58af408ff2c6e6383 | COC(=O)c1cc(Cl)cc2c1OCCCO2>>O=C(O)c1cc(Cl)cc2c1OCCCO2 | ClC=1C=C(C2=C(OCCCO2)C1)C(=O)OC.[OH-].[K+].Cl>>ClC=1C=C(C2=C(OCCCO2)C1)C(=O)O | C[O:3][C:2](=[O:1])[c:4]1[cH:5][c:6]([Cl:7])[cH:8][c:9]2[c:10]1[O:11][CH2:12][CH2:13][CH2:14][O:15]2>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([Cl:7])[cH:8][c:9]2[c:10]1[O:11][CH2:12][CH2:13][CH2:14][O:15]2 | COC(=O)c1cc(Cl)cc2c1OCCCO2 | O=C(O)c1cc(Cl)cc2c1OCCCO2 | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(c1)OCCCO2 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 84 | [{"value": 84.0, "product": "ClC=1C=C(C2=C(OCCCO2)C1)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of intermediate (5) (0.25 mol) and KOH (1 mol) in water (650 ml) was stirred and refluxed for 2 hours. The reaction mixture was cooled, acidified with HCl and the resulting precipitate was filtered off, washed with water, and dried, yielding 48 g of 8-chloro-3,4-dihydro-2H-1,5-benzodioxepin-6-carboxylic acid ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)OCCCO2 | Other | O | null | null | COC(=O)c1cc(Cl)cc2c1OCCCO2>O>O=C(O)c1cc(Cl)cc2c1OCCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3b4d9a4c496a4452ae9c46989d1e0c69 | BrCCCBr.COC(=O)c1ccc(OC)c(O)c1O>>COC(=O)c1ccc(OC)c2c1OCCCO2 | COC(C1=C(C(=C(C=C1)OC)O)O)=O.BrCCCBr.C(=O)([O-])[O-].[K+].[K+]>>COC1=CC=C(C2=C1OCCCO2)C(=O)OC | Br[CH2:14][CH2:15][CH2:16]Br.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH3:10])[c:11]([OH:17])[c:12]1[OH:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH3:10])[c:11]2[c:12]1[O:13][CH2:14][CH2:15][CH2:16][O:17]2 | BrCCCBr.COC(=O)c1ccc(OC)c(O)c1O | COC(=O)c1ccc(OC)c2c1OCCCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | c1d419ba122c3b8de019e7646b88bc33cf015fa0a84461e5f233e021ae1598c1 | 3a4296ab1122b8b150c8c66756a35bcf5ed04942f87f4ab6361d5944860b5919 | c1ccc2c(c1)OCCCO2 | Br-[CH2;D2;+0:1]-[C:2]-[CH2;D2;+0:3]-Br.[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10](-[OH;D1;+0:11]):[c:12]>>[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8]1:[c:10](:[c:12])-[O;H0;D2;+0:11]-[CH2;D2;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-1 | null | [] | null | null | 7 | HOUR | A mixture of 2,3-dihydroxy-4-methoxy benzoic acid methyl ester (0.45 mol), 1,3-dibromopropane (0.72 mol), K2CO3 (155 g) and CuO (3.6 g) in DMF (2500 ml) was stirred at 120° C. to 130° C. for 7 hours, cooled and filtered. The solvent was evaporated. HCl (aqueous solution of 0.5 N, 1000 ml)) was added. The mixture was ex... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Aromatic alcohol.Aromatic alcohol | Ether.Ether | null | c1ccc2c(c1)OCCCO2 | c1ccc2c(c1)OCCCO2 | HBr | CN(C)C=O | null | 7 | BrCCCBr.COC(=O)c1ccc(OC)c(O)c1O>CN(C)C=O>COC(=O)c1ccc(OC)c2c1OCCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d2bdae1019994c7aaf9cdb2c198814c4 | COC(=O)c1ccc(OC)c2c1OCCCO2>>COc1ccc(C(=O)O)c2c1OCCCO2 | [OH-].[Na+].COC1=CC=C(C2=C1OCCCO2)C(=O)OC>>COC1=CC=C(C2=C1OCCCO2)C(=O)O | C[O:9][C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:11]2[c:10]1[O:12][CH2:13][CH2:14][CH2:15][O:16]2)=[O:8]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[c:10]2[c:11]1[O:12][CH2:13][CH2:14][CH2:15][O:16]2 | COC(=O)c1ccc(OC)c2c1OCCCO2 | COc1ccc(C(=O)O)c2c1OCCCO2 | null | null | C1CCOC1 | Miscellaneous | Ester saponification (methyl deprotection) | 5cec4ccba5f10a1a475c49408d1acd0ffa4d5bb122bd1ad044ed7538c9ff072b | 8413620f40b868549edce10ed0cfc150fb551ff1c319f26d7a73cf9403b87fb8 | c1ccc2c(c1)OCCCO2 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c:7](-[#8:8]):[c;H0;D3;+0:9]2:[c;H0;D3;+0:10]:1-[O;H0;D2;+0:11]-[C:12]-[C:13]-[C:14]-[O;H0;D2;+0:15]-2>>[#8:8]-[c:7]1:[c:6]:[c:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c;H0;D3;+0:10]2:[c;H0;D3;+0:9]:1-[O;H0;D2;+0:11]-[C:12]-[C:13]-[C:14]-[O;H0;D2;+0:15]-2 | null | [] | null | null | 8 | HOUR | A NaOH solution (500 ml, 2N) was added to a solution of intermediate (7) in THF (250 ml). The mixture was stirred at room temperature overnight. The solvent was evaporated partially. The residue was extrated with DCM. The mixture was separated into its layers. The aqueous layer was acidified with a concentrated HCl sol... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Ether | Carboxylic acid.Ether.Ether | c1ccc2c(c1)OCCCO2 | c1ccc2c(c1)OCCCO2 | c1ccc2c(c1)OCCCO2 | Other | C1CCOC1 | null | 8 | COC(=O)c1ccc(OC)c2c1OCCCO2>C1CCOC1>COc1ccc(C(=O)O)c2c1OCCCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b0375aad16d44a158bac5acbb28333a8 | CC(C)(C)OC(=O)N1CC[C@@H](CNCc2ccccc2)[C@H](O)C1>>CC(C)(C)OC(=O)N1CC[C@@H](CN)[C@H](O)C1 | O[C@@H]1CN(CC[C@H]1CNCC1=CC=CC=C1)C(=O)OC(C)(C)C.[H][H]>>NC[C@H]1[C@@H](CN(CC1)C(=O)OC(C)(C)C)O | c1ccc(C[NH:13][CH2:12][C@@H:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:16][C@H:14]2[OH:15])cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]([CH2:12][NH2:13])[C@H:14]([OH:15])[CH2:16]1 | CC(C)(C)OC(=O)N1CC[C@@H](CNCc2ccccc2)[C@H](O)C1 | CC(C)(C)OC(=O)N1CC[C@@H](CN)[C@H](O)C1 | null | [Pd] | CO | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | C1CCNCC1 | [C:1]-[C:2]-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2]-[NH2;D1;+0:3] | null | [] | null | null | null | null | A mixture of 1,1-dimethylethyl (trans)-3-hydroxy4-[[(phenylmethyl)amino]methyl]-1-piperidinecarboxylate [described in WO-00/37461 as intermediate (1-d)] (0.023 mol) in methanol (100 ml) was hydrogenated with palladium-on-carbon (10%, 1 g) as a catalyst. After uptake of hydrogen (1 equivalent), the catalyst was filtered... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | C1CC[NH]CC1 | Other | [Pd].CO | null | null | CC(C)(C)OC(=O)N1CC[C@@H](CNCc2ccccc2)[C@H](O)C1>[Pd].CO>CC(C)(C)OC(=O)N1CC[C@@H](CN)[C@H](O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9241ba2bd9ba484a94d312b23bf9c009 | CC(C)(C)OC(=O)N1CC[C@@H](CNCc2ccccc2)[C@H](O)C1>>CC(C)(C)OC(=O)N1CC[C@@H](CN)[C@H](O)C1 | O[C@@H]1CN(CC[C@H]1CNCC1=CC=CC=C1)C(=O)OC(C)(C)C.[H][H]>>NC[C@H]1[C@@H](CN(CC1)C(=O)OC(C)(C)C)O | c1ccc(C[NH:13][CH2:12][C@@H:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:16][C@H:14]2[OH:15])cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]([CH2:12][NH2:13])[C@H:14]([OH:15])[CH2:16]1 | CC(C)(C)OC(=O)N1CC[C@@H](CNCc2ccccc2)[C@H](O)C1 | CC(C)(C)OC(=O)N1CC[C@@H](CN)[C@H](O)C1 | null | [Pd] | CO | Deprotection | OtherReaction | 93c46c2f9981b731115295839d7158a8a73faedd00707b7604ace2fa5f580cbc | f6571fb5b7780a2b467937abfba91ba7d787f19d503265f299ff4a25a08963bd | C1CCNCC1 | [C:1]-[C:2]-[NH;D2;+0:3]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2]-[NH2;D1;+0:3] | 72.9 | [{"value": 72.9, "product": "NC[C@H]1[C@@H](CN(CC1)C(=O)OC(C)(C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of intermediate (21) (0.028 mol) in methanol (100 ml) was hydrogenated with palladium-on-carbon (10%, 2 g) as a catalyst. After uptake of hydrogen (1 equivalent) the catalyst was filtered off and the filtrate was evaporated, yielding 4.7 g of 1,1-dimethylethyl (3S-trans)-4-(aminomethyl)-3-hydroxy-1-piperidine... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Primary amine | c1ccccc1 | null | C1CC[NH]CC1 | Other | [Pd].CO | null | null | CC(C)(C)OC(=O)N1CC[C@@H](CNCc2ccccc2)[C@H](O)C1>[Pd].CO>CC(C)(C)OC(=O)N1CC[C@@H](CN)[C@H](O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bcc52f18ea254431843935fb7c8bcc82 | CO[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1COS(=O)(=O)c1ccc(C)cc1.N>>CO[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1CN | CC1=CC=C(C=C1)S(=O)(=O)OC[C@H]1[C@@H](CN(CC1)C(=O)OC(C)(C)C)OC.N>>NC[C@H]1[C@@H](CN(CC1)C(=O)OC(C)(C)C)OC | Cc1ccc(S(=O)(=O)O[CH2:16][C@H:15]2[C@H:3]([O:2][CH3:1])[CH2:4][N:5]([C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:13][CH2:14]2)cc1.[NH3:17]>>[CH3:1][O:2][C@@H:3]1[CH2:4][N:5]([C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:13][CH2:14][C@H:15]1[CH2:16][NH2:17] | CO[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1COS(=O)(=O)c1ccc(C)cc1.N | CO[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1CN | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 5aa46c46e8998fd2466004b65fd3c08103725e888876ac3e2ac0662ffe3b2f16 | 7960d8ab1775b6ecd2283b27f871a0f456284d9cc378526ddef93e6c31d6b8b8 | C1CCNCC1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]):c:c:1.[NH3;D0;+0:5]>>[C:3]-[C:2](-[CH2;D2;+0:1]-[NH2;D1;+0:5])-[C:4] | null | [] | null | null | null | null | A mixture of intermediate (23) (0.065 mol) in THF (250 ml) was treated with liquid NH3 in an autoclave at 125° C. during 16 hours. The reaction mixture was filtered and the filtrate was evaporated. The residue was partitioned between a 5% aqueous NaOH solution and DCM. The organic layer was separated, dried, filtered a... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate | Primary amine | c1ccccc1 | null | C1CC[NH]CC1 | TsOH.HO- | C1CCOC1 | null | null | CO[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1COS(=O)(=O)c1ccc(C)cc1.N>C1CCOC1>CO[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1CN |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-727062505c4d47119f0152126045a718 | C1CCNC1.CCOC(=O)c1nc(-c2ccc(Cl)cc2Cl)n(-c2ccc(Cl)cc2)c1CBr>>CCOC(=O)c1nc(-c2ccc(Cl)cc2Cl)n(-c2ccc(Cl)cc2)c1CN1CCCC1 | O.BrCC1=C(N=C(N1C1=CC=C(C=C1)Cl)C1=C(C=C(C=C1)Cl)Cl)C(=O)OCC.C(C)(C)N(CC)C(C)C.N1CCCC1>>ClC1=CC=C(C=C1)N1C(=NC(=C1CN1CCCC1)C(=O)OCC)C1=C(C=C(C=C1)Cl)Cl | [NH:27]1[CH2:28][CH2:29][CH2:30][CH2:31]1.Br[CH2:26][c:25]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]2[Cl:16])[n:17]1-[c:18]1[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14]... | C1CCNC1.CCOC(=O)c1nc(-c2ccc(Cl)cc2Cl)n(-c2ccc(Cl)cc2)c1CBr | CCOC(=O)c1nc(-c2ccc(Cl)cc2Cl)n(-c2ccc(Cl)cc2)c1CN1CCCC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(-c2ncc(CN3CCCC3)n2-c2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[#7;a:3](-[c:4]):[c:5]:[#7;a:6]:[c:7]:1-[C:8](-[#8:9])=[O;D1;H0:10].[C:11]1-[C:12]-[C:13]-[C:14]-[NH;D2;+0:15]-1>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[#7;a:6]:[c:5]:[#7;a:3](-[c:4]):[c:2]:1-[CH2;D2;+0:1]-[N;H0;D3;+0:15]1-[C:11]-[C:12]-[C:13]-[C:14]-1 | 32.3 | [{"value": 32.0, "product": "ClC1=CC=C(C=C1)N1C(=NC(=C1CN1CCCC1)C(=O)OCC)C1=C(C=C(C=C1)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.3, "product": "ClC1=CC=C(C=C1)N1C(=NC(=C1CN1CCCC1)C(=O)OCC)C1=C(C=C(C=C1)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Part B: To a magnetically stirred solution of ethyl 5-bromomethyl-1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-1H-imidazole-4-carboxylate (11.69 g, 23.9 mmol) in acetonitrile (40 ml) is added diisopropylethylamine (DIPEA) (5.2 ml, 30 mmol) and pyrrolidine (1.7 g, 23.9 mmol) and the resulting solution is reacted at room te... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1c[nH]cn1.c1ccccc1.c1ccccc1.C1CC[NH]C1 | HBr | C(C)#N | null | null | C1CCNC1.CCOC(=O)c1nc(-c2ccc(Cl)cc2Cl)n(-c2ccc(Cl)cc2)c1CBr>C(C)#N>CCOC(=O)c1nc(-c2ccc(Cl)cc2Cl)n(-c2ccc(Cl)cc2)c1CN1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-927809a31c014c9ab1479cdf5252b408 | CCOC(=O)c1nc(-c2ccc(Cl)cc2Cl)n(-c2ccc(Cl)cc2)c1CN1CCCC1.NC1CCCCC1>>O=C(NC1CCCCC1)c1nc(-c2ccc(Cl)cc2Cl)n(-c2ccc(Cl)cc2)c1CN1CCCC1 | C(=O)(O)[O-].[Na+].C1(CCCCC1)N.[Al](C)(C)C.ClC1=CC=C(C=C1)N1C(=NC(=C1CN1CCCC1)C(=O)OCC)C1=C(C=C(C=C1)Cl)Cl>>C1(CCCCC1)NC(=O)C=1N=C(N(C1CN1CCCC1)C1=CC=C(C=C1)Cl)C1=C(C=C(C=C1)Cl)Cl | CCO[C:2](=[O:1])[c:10]1[n:11][c:12](-[c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][c:19]2[Cl:20])[n:21](-[c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[c:29]1[CH2:30][N:31]1[CH2:32][CH2:33][CH2:34][CH2:35]1.[NH2:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1>>[O:1]=[C:2]([NH:3][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2... | CCOC(=O)c1nc(-c2ccc(Cl)cc2Cl)n(-c2ccc(Cl)cc2)c1CN1CCCC1.NC1CCCCC1 | O=C(NC1CCCCC1)c1nc(-c2ccc(Cl)cc2Cl)n(-c2ccc(Cl)cc2)c1CN1CCCC1 | null | null | ClCCl.CCCCCCC | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=C(NC1CCCCC1)c1nc(-c2ccccc2)n(-c2ccccc2)c1CN1CCCC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](-[c:7]):[c:8]:1-[C:9].[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13]>>[C:9]-[c:8]1:[#7;a:6](-[c:7]):[c:5]:[#7;a:4]:[c:3]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:12]-[C:11](-[C:10])-[C:13] | 53 | [{"value": 53.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Part C: Cyclohexylamine (0.91 ml, 8 mmol) is dissolved in dichloromethane (20 ml) and (CH3)3Al (4 ml of a 2 M solution in heptane, 8 mmol) is added. The resulting mixture is stirred for 10 minutes at room temperature and ethyl 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-(pyrrolidin-1-ylmethyl)-1H-imidazole-4-carboxylat... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | C1CCCCC1.c1c[nH]cn1.c1ccccc1.c1ccccc1.C1CC[NH]C1 | HO- | ClCCl.CCCCCCC | null | 0.166667 | CCOC(=O)c1nc(-c2ccc(Cl)cc2Cl)n(-c2ccc(Cl)cc2)c1CN1CCCC1.NC1CCCCC1>ClCCl.CCCCCCC>O=C(NC1CCCCC1)c1nc(-c2ccc(Cl)cc2Cl)n(-c2ccc(Cl)cc2)c1CN1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8ac91ea132b74e3ab3e10dd910e37d62 | COc1cc2c(N)ncnc2cc1OCC1CCN(C)CC1.O=C=Nc1c(Cl)cccc1Cl>>COc1cc2c(NC(=O)Nc3c(Cl)cccc3Cl)ncnc2cc1OCC1CCN(C)CC1 | ClC1=C(C(=CC=C1)Cl)N=C=O.NC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C>>ClC1=C(C(=CC=C1)Cl)NC(=O)NC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH2:7])[n:19][cH:20][n:21][c:22]2[cH:23][c:24]1[O:25][CH2:26][CH:27]1[CH2:28][CH2:29][N:30]([CH3:31])[CH2:32][CH2:33]1.[C:8](=[O:9])=[N:10][c:11]1[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]1[Cl:18]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][C:8](=[O:9])[NH:10][c:11]3[c:12]([Cl:13])[... | COc1cc2c(N)ncnc2cc1OCC1CCN(C)CC1.O=C=Nc1c(Cl)cccc1Cl | COc1cc2c(NC(=O)Nc3c(Cl)cccc3Cl)ncnc2cc1OCC1CCN(C)CC1 | null | null | CO.CN(C)C=O.C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1ncnc2cc(OCC3CCNCC3)ccc12 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[O;D1;H0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[O;D1;H0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | 19.2 | [{"value": 19.2, "product": "ClC1=C(C(=CC=C1)Cl)NC(=O)NC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 2,6Dichlorophenyl isocyanate (0.075 g) was added to a solution of 4amino-6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazoline (0.093 g) in a mixture of methylene chloride (2 ml) and DMF (0.1 ml) and the reaction mixture was stirred at ambient temperature for 16 hours. The resultant solid was isolated, redissolved in ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2ncncc2c1.C1CC[NH]CC1 | null | CO.CN(C)C=O.C(Cl)Cl | null | 16 | COc1cc2c(N)ncnc2cc1OCC1CCN(C)CC1.O=C=Nc1c(Cl)cccc1Cl>CO.CN(C)C=O.C(Cl)Cl>COc1cc2c(NC(=O)Nc3c(Cl)cccc3Cl)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1b7dbd0f593d4296aea6ff648e17ccf0 | NC=O.Nc1cc(F)ccc1C(=O)O>>O=c1[nH]cnc2cc(F)ccc12 | NC1=C(C(=O)O)C=CC(=C1)F.C(=O)N.O>>FC1=CC=C2C(NC=NC2=C1)=O | O=[CH:4][NH2:3].O[C:2](=[O:1])[c:12]1[c:6]([NH2:5])[cH:7][c:8]([F:9])[cH:10][cH:11]1>>[O:1]=[c:2]1[nH:3][cH:4][n:5][c:6]2[cH:7][c:8]([F:9])[cH:10][cH:11][c:12]12 | NC=O.Nc1cc(F)ccc1C(=O)O | O=c1[nH]cnc2cc(F)ccc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | fa5379c8482cb80a00fcd8aa505f907d855c75e02a2f2eed0f1501b224d6fd3c | 42d7d0d29a255bcbf4fdad9c0b39487d2cf609ac6796e99c9c033d59efbdbdc9 | O=c1[nH]cnc2ccccc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7].O=[CH;D2;+0:8]-[NH2;D1;+0:9]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:9]:[cH;D2;+0:8]:[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3]:1:[c:4] | null | [] | null | null | null | null | A solution of 2-amino-4-fluorobenzoic acid (3 g) in formamide (30 ml) was heated to 150° C. for 6 hours. The reaction mixture was poured onto a 1:1 mixture of ice and water (250 ml) and the precipitated solid was collected, washed with water and dried to give 7-fluoro-3,4-dihydroquinazolin-4-one (2.6 g)
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amide.Primary amine | null | c1ccccc1 | c1ccc2cncnc2c1 | c1ccc2cncnc2c1 | HO- | null | null | null | NC=O.Nc1cc(F)ccc1C(=O)O>>O=c1[nH]cnc2cc(F)ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0554dbf9a47943f5b233eaed385f3459 | CSc1ncnc2cc(O)ccc12.OC/C=C/CN1CCOCC1>>CSc1ncnc2cc(OC/C=C/CN3CCOCC3)ccc12 | O1CCN(CC1)C/C=C/CO.OC1=CC=C2C(=NC=NC2=C1)SC>>CSC1=NC=NC2=CC(=CC=C12)OC\C=C\CN1CCOCC1 | [CH3:1][S:2][c:3]1[n:4][cH:5][n:6][c:7]2[cH:8][c:9]([OH:10])[cH:21][cH:22][c:23]12.O[CH2:11]/[CH:12]=[CH:13]/[CH2:14][N:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1>>[CH3:1][S:2][c:3]1[n:4][cH:5][n:6][c:7]2[cH:8][c:9]([O:10][CH2:11]/[CH:12]=[CH:13]/[CH2:14][N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)[cH:21][cH:22][c:... | CSc1ncnc2cc(O)ccc12.OC/C=C/CN1CCOCC1 | CSc1ncnc2cc(OC/C=C/CN3CCOCC3)ccc12 | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | C(=C/CN1CCOCC1)\COc1ccc2cncnc2c1 | O-[CH2;D2;+0:1]/[C:2]=[C:3]/[C:4]-[#7:5].[#7;a:6]:[c:7]:[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[#7:5]-[C:4]/[C:3]=[C:2]/[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[c:9](:[c:11]):[c:8]:[c:7]:[#7;a:6] | 55.6 | [{"value": 55.6, "product": "CSC1=NC=NC2=CC(=CC=C12)OC\\C=C\\CN1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using an analogous procedure to that described in the second last paragraph of Note [12] above, (E)-4-morpholinobut-2-en-1-ol (J. Med. Chem., 1972, 15 110-112; 1.27 g), was reacted with 7-hydroxy-4-methylthioquinazoline (1.2 g) to give 4-methylthio -7-[(E)-4-morpholinobut-2-en-1-yloxy]quinazoline (1.15 g); NMR Spectrum... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2ncncc2c1.C1COCC[NH]1 | HO- | null | null | null | CSc1ncnc2cc(O)ccc12.OC/C=C/CN1CCOCC1>>CSc1ncnc2cc(OC/C=C/CN3CCOCC3)ccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ee3af91388349f0b7cf2785f42332cf | CNCCO.COCCBr>>COCCN(C)CCO | CNCCO.COCCBr.C(C)N(CC)CC>>COCCN(C)CCO | [NH:5]([CH3:6])[CH2:7][CH2:8][OH:9].Br[CH2:4][CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:6])[CH2:7][CH2:8][OH:9] | CNCCO.COCCBr | COCCN(C)CCO | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | null | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C;D1;H3:7])-[C:5]-[C:4] | 31.3 | [{"value": 31.0, "product": "COCCN(C)CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.3, "product": "COCCN(C)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-methylaminoethanol (5.4 g), 2-bromoethyl methyl ether (10 g), triethylamine (10 ml) and acetonitrile (70 ml) was stirred and heated to reflux for 16 hours. The mixture was cooled to ambient temperature and filtered. The filtrate was evaporated and the residue was triturated under diethyl ether. The organ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | null | HBr | C(C)#N | null | null | CNCCO.COCCBr>C(C)#N>COCCN(C)CCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e39095663e784efdaa75073a20978fac | C#CCCCCN1CCOCC1.COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1OS(=O)(=O)C(F)(F)F>>COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1C#CCCCCN1CCOCC1 | O1CCN(CC1)CCCCC#C.BrC1=C(OC2=NC=NC3=CC(=C(C=C23)OC)OS(=O)(=O)C(F)(F)F)C=CC(=C1)F>>BrC1=C(OC2=NC=NC3=CC(=C(C=C23)OC)C#CCCCCN2CCOCC2)C=CC(=C1)F | [CH:22]#[C:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[CH2:29][CH2:30][O:31][CH2:32][CH2:33]1.O=S(=O)(O[c:21]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]3[Br:15])[n:16][cH:17][n:18][c:19]2[cH:20]1)C(F)(F)F>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]([F... | C#CCCCCN1CCOCC1.COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1OS(=O)(=O)C(F)(F)F | COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1C#CCCCCN1CCOCC1 | null | null | null | C-C Coupling | Sonogashira alkyne_aryl OTf | 523611a94beb1862a838986e1c1be72d3c8cef4977ba92ce7cb712e2a55a2c9e | 32719cc33361c7806519cb2ede8ea1e1b28ea02ade479d3965d328b6ee502fdc | C(#Cc1ccc2c(Oc3ccccc3)ncnc2c1)CCCCN1CCOCC1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:2:[c:9]:[c:10]:1-[#8:11].[C:12]-[C:13]#[CH;D1;+0:14]>>[#8:11]-[c:10]1:[c:9]:[c:8]2:[c:7]:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:2:[c:2]:[c;H0;D3;+0:1]:1-[C;H0;D2;+0:14]#[C:13]-[C:12] | null | [] | null | null | null | null | Using an analogous procedure to that described in the second last paragraph of Note [115] above, 6-morpholino-1-hexyne was reacted with 4-(2-bromo-4-fluorophenoxy)-6-methoxy-7-trifluoromethanesulphonyloxyquinazoline to give 4-(2-bromo-4-fluorophenoxy)-6-methoxy-7-(6-morpholino-1-hexynyl)quinazoline, NMR Spectrum: (DMSO... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Alkyne | Alkyne | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1.C1COCC[NH]1 | TfOH.HO- | null | null | null | C#CCCCCN1CCOCC1.COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1OS(=O)(=O)C(F)(F)F>>COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1C#CCCCCN1CCOCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c8f5e5dd98b346de8f45e1bdf9ef3478 | C#CCCCCn1ccnc1C.COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1OS(=O)(=O)C(F)(F)F>>COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1C#CCCCCn1ccnc1C | CC=1N(C=CN1)CCCCC#C.BrC1=C(OC2=NC=NC3=CC(=C(C=C23)OC)OS(=O)(=O)C(F)(F)F)C=CC(=C1)F>>BrC1=C(OC2=NC=NC3=CC(=C(C=C23)OC)C#CCCCCN2C(=NC=C2)C)C=CC(=C1)F | [CH:22]#[C:23][CH2:24][CH2:25][CH2:26][CH2:27][n:28]1[cH:29][cH:30][n:31][c:32]1[CH3:33].O=S(=O)(O[c:21]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]3[Br:15])[n:16][cH:17][n:18][c:19]2[cH:20]1)C(F)(F)F>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]([F:12]... | C#CCCCCn1ccnc1C.COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1OS(=O)(=O)C(F)(F)F | COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1C#CCCCCn1ccnc1C | null | null | null | C-C Coupling | Sonogashira alkyne_aryl OTf | 523611a94beb1862a838986e1c1be72d3c8cef4977ba92ce7cb712e2a55a2c9e | 32719cc33361c7806519cb2ede8ea1e1b28ea02ade479d3965d328b6ee502fdc | C(#Cc1ccc2c(Oc3ccccc3)ncnc2c1)CCCCn1ccnc1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:2:[c:9]:[c:10]:1-[#8:11].[C:12]-[C:13]#[CH;D1;+0:14]>>[#8:11]-[c:10]1:[c:9]:[c:8]2:[c:7]:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:2:[c:2]:[c;H0;D3;+0:1]:1-[C;H0;D2;+0:14]#[C:13]-[C:12] | null | [] | null | null | null | null | Using an analogous procedure to that described in the second last paragraph of Note [115] above, 6-(2-methylimidazol-1-yl)-1-hexyne was reacted with 4-(2-bromo-4-fluorophenoxy)-6-methoxy-7-trifluoromethanesulphonyloxyquinazoline to give 4-(2-bromo-4-fluorophenoxy)-6-methoxy-7-[6-(2-methylimidazol-1-yl)-1-hexynyl]quinaz... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Alkyne | Alkyne | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1.c1ncc[nH]1 | TfOH.HO- | null | null | null | C#CCCCCn1ccnc1C.COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1OS(=O)(=O)C(F)(F)F>>COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1C#CCCCCn1ccnc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a8afa24a1c044fc791e16a63b6c2a83c | C#CCN(C)C.COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1OS(=O)(=O)C(F)(F)F>>COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1C#CCN(C)C | CN(CC#C)C.BrC1=C(OC2=NC=NC3=CC(=C(C=C23)OC)OS(=O)(=O)C(F)(F)F)C=CC(=C1)F>>BrC1=C(OC2=NC=NC3=CC(=C(C=C23)OC)C#CCN(C)C)C=CC(=C1)F | [CH:22]#[C:23][CH2:24][N:25]([CH3:26])[CH3:27].O=S(=O)(O[c:21]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]3[Br:15])[n:16][cH:17][n:18][c:19]2[cH:20]1)C(F)(F)F>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([O:7][c:8]3[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]3[Br:15])[n:16][cH:17][n:18]... | C#CCN(C)C.COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1OS(=O)(=O)C(F)(F)F | COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1C#CCN(C)C | null | null | null | C-C Coupling | Sonogashira alkyne_aryl OTf | 523611a94beb1862a838986e1c1be72d3c8cef4977ba92ce7cb712e2a55a2c9e | 32719cc33361c7806519cb2ede8ea1e1b28ea02ade479d3965d328b6ee502fdc | c1ccc(Oc2ncnc3ccccc23)cc1 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:2:[c:9]:[c:10]:1-[#8:11].[C:12]-[C:13]#[CH;D1;+0:14]>>[#8:11]-[c:10]1:[c:9]:[c:8]2:[c:7]:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:2:[c:2]:[c;H0;D3;+0:1]:1-[C;H0;D2;+0:14]#[C:13]-[C:12] | null | [] | null | null | null | null | Using an analogous procedure to that described in the second last paragraph of Note [115] above, 3-dimethylamino-1-propyne was reacted with 4-(2-bromo-4-fluorophenoxy)-6-methoxy-7-trifluoromethanesulphonyloxyquinazoline to give 4-(2-bromo-4-fluorophenoxy)-6-methoxy-7-(3-dimethylamino-1-propynyl)quinazoline; NMR Spectru... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Alkyne | Alkyne | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1 | TfOH.HO- | null | null | null | C#CCN(C)C.COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1OS(=O)(=O)C(F)(F)F>>COc1cc2c(Oc3ccc(F)cc3Br)ncnc2cc1C#CCN(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e7a45301d8946d69abc66b372b0dfab | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.Cc1ccc(C(=O)N(C)C)c(C)c1N>>Cc1ccc(C(=O)N(C)C)c(C)c1N=C=O | C(=O)(OC(C)(C)C)OC(=O)OC(C)(C)C.NC=1C(=C(C(=O)N(C)C)C=CC1C)C>>CN(C(=O)C=1C(=C(C(=CC1)C)N=C=O)C)C | CC(C)(C)OC(=O)O[C:15](OC(C)(C)C)=[O:16].[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]([CH3:9])[CH3:10])[c:11]([CH3:12])[c:13]1[NH2:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[N:8]([CH3:9])[CH3:10])[c:11]([CH3:12])[c:13]1[N:14]=[C:15]=[O:16] | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.Cc1ccc(C(=O)N(C)C)c(C)c1N | Cc1ccc(C(=O)N(C)C)c(C)c1N=C=O | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Miscellaneous | OtherReaction | 3cd5f0aa717382a4745722cddec8f691b422edb8a5dc1a0f3fbce8bff934ce45 | b9e1ae76a444e99a6d4011e4747d844adf461170a5129e76308b970e3bb21eec | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-C)(-C)-C.[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A solution of di-tert-butyl dicarbonate (0.081 g) in methylene chloride (1.6 ml) and a solution of 3-amino-N,N,2,4-tetramethylbenzamide (J. Chem. Soc., Perkin Trans. I, 1973, 1-4; 0.072 g) in methylene chloride (1.0 ml) were added in turn to a solution of 4-dimethylaminopyridine (0.004 g) in methylene chloride (0.4 ml)... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carbonic Ester.Carbonic Ester.Primary amine.Boc.Boc | Isocyanate | null | null | c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.C(Cl)Cl | null | null | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.Cc1ccc(C(=O)N(C)C)c(C)c1N>CN(C1=CC=NC=C1)C.C(Cl)Cl>Cc1ccc(C(=O)N(C)C)c(C)c1N=C=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a352f3faeaec4e41acb986fc86af8a56 | COc1cc2ncnc(N)c2cc1OC.O=C=Nc1c(Cl)cccc1Cl>>COc1cc2ncnc(NC(=O)Nc3c(Cl)cccc3Cl)c2cc1OC | ClC1=C(C(=CC=C1)Cl)N=C=O.NC1=NC=NC2=CC(=C(C=C12)OC)OC>>ClC1=C(C(=CC=C1)Cl)NC(=O)NC1=NC=NC2=CC(=C(C=C12)OC)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([NH2:10])[c:22]2[cH:23][c:24]1[O:25][CH3:26].[C:11](=[O:12])=[N:13][c:14]1[c:15]([Cl:16])[cH:17][cH:18][cH:19][c:20]1[Cl:21]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([NH:10][C:11](=[O:12])[NH:13][c:14]3[c:15]([Cl:16])[cH:17][cH:18][cH:19][c:20]3[Cl:21])[c:... | COc1cc2ncnc(N)c2cc1OC.O=C=Nc1c(Cl)cccc1Cl | COc1cc2ncnc(NC(=O)Nc3c(Cl)cccc3Cl)c2cc1OC | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1ncnc2ccccc12 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[O;D1;H0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[O;D1;H0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1)-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13] | null | [] | null | null | null | null | Using an analogous procedure to that described in Example 3, 2,6-dichlorophenyl isocyanate was reacted with 4-amino-6,7-dimethoxyquinazoline (European Patent Application No. 30156, Chemical Abstract volume 95, abstract 187290) to give the title compound; NMR Spectrum: (DMSOd6) 3.96 (s, 3H), 7.31 (m, 2H), 7.38 (t, 1H), ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2ncncc2c1.c1ccccc1 | null | null | null | null | COc1cc2ncnc(N)c2cc1OC.O=C=Nc1c(Cl)cccc1Cl>>COc1cc2ncnc(NC(=O)Nc3c(Cl)cccc3Cl)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8db3ef97975143c1821bcb5b829ec461 | Nc1ncnc2ccsc12.O=C=Nc1c(Cl)cccc1Cl>>O=C(Nc1c(Cl)cccc1Cl)Nc1ncnc2ccsc12 | ClC1=C(C(=CC=C1)Cl)N=C=O.NC=1C2=C(N=CN1)C=CS2>>ClC1=C(C(=CC=C1)Cl)NC(=O)NC=1C2=C(N=CN1)C=CS2 | [NH2:12][c:13]1[n:14][cH:15][n:16][c:17]2[cH:18][cH:19][s:20][c:21]12.[O:1]=[C:2]=[N:3][c:4]1[c:5]([Cl:6])[cH:7][cH:8][cH:9][c:10]1[Cl:11]>>[O:1]=[C:2]([NH:3][c:4]1[c:5]([Cl:6])[cH:7][cH:8][cH:9][c:10]1[Cl:11])[NH:12][c:13]1[n:14][cH:15][n:16][c:17]2[cH:18][cH:19][s:20][c:21]12 | Nc1ncnc2ccsc12.O=C=Nc1c(Cl)cccc1Cl | O=C(Nc1c(Cl)cccc1Cl)Nc1ncnc2ccsc12 | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1ncnc2ccsc12 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1:[#16;a:8]:[c:9].[O;D1;H0:10]=[C;H0;D2;+0:11]=[N;H0;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[O;D1;H0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1:[#16;a:8]:[c:9])-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15] | 229.1 | [{"value": 229.1, "product": "ClC1=C(C(=CC=C1)Cl)NC(=O)NC=1C2=C(N=CN1)C=CS2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,6-Dichlorophenyl isocyanate (0.075 g) was added to a mixture of 4-aminothieno[3,2-d]pyrimidine (Tetrahedron, 1971, 27, 487; 0.201 g) and acetonitrile (16 ml) and the resultant mixture was stirred at ambient temperature for 16 hours. The precipitate was isolated and washed in turn with diethyl ether and methanol. Ther... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ncc2sccc2n1 | null | C(C)#N | null | null | Nc1ncnc2ccsc12.O=C=Nc1c(Cl)cccc1Cl>C(C)#N>O=C(Nc1c(Cl)cccc1Cl)Nc1ncnc2ccsc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-994dff53fafe457cbc3288e93b74b995 | NCCN1CCCCC1.O=C(O)/C=C/c1cc2ncnc(NC(=O)Nc3c(Cl)cccc3Cl)c2s1>>O=C(/C=C/c1cc2ncnc(NC(=O)Nc3c(Cl)cccc3Cl)c2s1)NCCN1CCCCC1 | C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-].Cl.ClC1=C(C(=CC=C1)Cl)NC(NC=1C2=C(N=CN1)C=C(S2)/C=C/C(=O)O)=O.N1(CCCCC1)CCN.C(C)N(CC)CC>>ClC1=C(C(=CC=C1)Cl)NC(NC=1C2=C(N=CN1)C=C(S2)/C=C/C(=O)NCCN2CCCCC2)=O | [NH2:26][CH2:27][CH2:28][N:29]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1.O[C:2](=[O:1])/[CH:3]=[CH:4]/[c:5]1[cH:6][c:7]2[n:8][cH:9][n:10][c:11]([NH:12][C:13](=[O:14])[NH:15][c:16]3[c:17]([Cl:18])[cH:19][cH:20][cH:21][c:22]3[Cl:23])[c:24]2[s:25]1>>[O:1]=[C:2](/[CH:3]=[CH:4]/[c:5]1[cH:6][c:7]2[n:8][cH:9][n:10][c:11]([NH:... | NCCN1CCCCC1.O=C(O)/C=C/c1cc2ncnc(NC(=O)Nc3c(Cl)cccc3Cl)c2s1 | O=C(/C=C/c1cc2ncnc(NC(=O)Nc3c(Cl)cccc3Cl)c2s1)NCCN1CCCCC1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(/C=C/c1cc2ncnc(NC(=O)Nc3ccccc3)c2s1)NCCN1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4]/[c:5](:[#16;a:6]):[c:7]:[c:8]:[#7;a:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5](/[C:4]=[C:3]/[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:12]-[C:11]-[C:10]):[c:7]:[c:8]:[#7;a:9] | 67.9 | [{"value": 67.9, "product": "ClC1=C(C(=CC=C1)Cl)NC(NC=1C2=C(N=CN1)C=C(S2)/C=C/C(=O)NCCN2CCCCC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Diphenylphosphoryl azide (0.085 ml) was added to a mixture of (E)-3-{4-[3-(2,6-dichlorophenyl)ureido]thieno[3,2-d]pyrimidin-6-yl)acrylic acid hydrochloride salt (0.11 g), 2-piperidinoethylamine (0.064 g), triethylamine (0.07 ml) and DMF (1.5 ml). The mixture was stirred at ambient temperature for 16 hours. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ncc2sccc2n1.c1ccccc1.C1CC[NH]CC1 | HO- | CN(C)C=O | null | 16 | NCCN1CCCCC1.O=C(O)/C=C/c1cc2ncnc(NC(=O)Nc3c(Cl)cccc3Cl)c2s1>CN(C)C=O>O=C(/C=C/c1cc2ncnc(NC(=O)Nc3c(Cl)cccc3Cl)c2s1)NCCN1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8922c6727354989b9cc9e4f75720cd0 | COc1cc2c(N)ncnc2cc1OCC1CCN(C)CC1.O=C=NCc1ccccc1>>COc1cc2c(NC(=O)NCc3ccccc3)ncnc2cc1OCC1CCN(C)CC1 | C(C1=CC=CC=C1)N=C=O.NC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C>>C(C1=CC=CC=C1)NC(=O)NC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH2:7])[n:18][cH:19][n:20][c:21]2[cH:22][c:23]1[O:24][CH2:25][CH:26]1[CH2:27][CH2:28][N:29]([CH3:30])[CH2:31][CH2:32]1.[C:8](=[O:9])=[N:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][C:8](=[O:9])[NH:10][CH2:11][c:12]3[cH:13][cH:14]... | COc1cc2c(N)ncnc2cc1OCC1CCN(C)CC1.O=C=NCc1ccccc1 | COc1cc2c(NC(=O)NCc3ccccc3)ncnc2cc1OCC1CCN(C)CC1 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCc1ccccc1)Nc1ncnc2cc(OCC3CCNCC3)ccc12 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[O;D1;H0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[C:11]-[c:12]>>[O;D1;H0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[C:11]-[c:12])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | null | [] | 35 | CELSIUS | null | null | Using an analogous procedure to that described in Example 1 except that the reaction mixture was heated to 35° C. for 16 hours, benzyl isocyanate was reacted within 4-amino-6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazoline to give the title compound; NMR Spectrum: (DMSOd6): 1.3-1.5 (m, 2H), 1.8-1.9 (m, 4H), 1.95 (... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2ncncc2c1.C1CC[NH]CC1 | null | null | 35 | null | COc1cc2c(N)ncnc2cc1OCC1CCN(C)CC1.O=C=NCc1ccccc1>>COc1cc2c(NC(=O)NCc3ccccc3)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d6a5e42628a64b629fe82124f44b19d9 | COc1cc2c(N)ncnc2cc1OCC1CCN(C)CC1.O=C=NCCc1ccccc1>>COc1cc2c(NC(=O)NCCc3ccccc3)ncnc2cc1OCC1CCN(C)CC1 | C(CC1=CC=CC=C1)N=C=O.NC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)NC(=O)NCCC1=CC=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH2:7])[n:19][cH:20][n:21][c:22]2[cH:23][c:24]1[O:25][CH2:26][CH:27]1[CH2:28][CH2:29][N:30]([CH3:31])[CH2:32][CH2:33]1.[C:8](=[O:9])=[N:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][c:13... | COc1cc2c(N)ncnc2cc1OCC1CCN(C)CC1.O=C=NCCc1ccccc1 | COc1cc2c(NC(=O)NCCc3ccccc3)ncnc2cc1OCC1CCN(C)CC1 | null | null | null | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCCc1ccccc1)Nc1ncnc2cc(OCC3CCNCC3)ccc12 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[C;H0;D2;+0:4]=[O;D1;H0:5].[NH2;D1;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1 | null | [] | null | null | null | null | Using an analogous procedure to that described in Example 3, phenethyl isocyanate was reacted with 4-amino-6methoxy-7-(N-methylpiperidin4ylmethoxy)quinazoline to give the title compound; NMR Spectrum: (CDCl3) 1.48 (m, 2H), 1.98 (m, 5H), 2.29 (s, 3H), 2.91 (m, 4H), 3.7 (q, 2H), 4.02 (d, 5H), 7.28 (m, partially obscured ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2ncncc2c1.C1CC[NH]CC1 | null | null | null | null | COc1cc2c(N)ncnc2cc1OCC1CCN(C)CC1.O=C=NCCc1ccccc1>>COc1cc2c(NC(=O)NCCc3ccccc3)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5236f07c1de741cbac7db4b973b3770a | COc1cc2c(NC(=O)Nc3c(Cl)cccc3Cl)ncnc2cc1OCCCN1CCC(CNC(=O)OC(C)(C)C)CC1>>COc1cc2c(NC(=O)Nc3c(Cl)cccc3Cl)ncnc2cc1OCCCN1CCC(CN)CC1 | C(C)(C)(C)OC(=O)NCC1CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)NC(=O)NC1=C(C=CC=C1Cl)Cl)OC.FC(C(=O)O)(F)F>>NCC1CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)NC(=O)NC1=C(C=CC=C1Cl)Cl)OC | CC(C)(C)OC(=O)[NH:34][CH2:33][CH:32]1[CH2:31][CH2:30][N:29]([CH2:28][CH2:27][CH2:26][O:25][c:24]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([NH:7][C:8](=[O:9])[NH:10][c:11]4[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]4[Cl:18])[n:19][cH:20][n:21][c:22]3[cH:23]2)[CH2:36][CH2:35]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][C:8](... | COc1cc2c(NC(=O)Nc3c(Cl)cccc3Cl)ncnc2cc1OCCCN1CCC(CNC(=O)OC(C)(C)C)CC1 | COc1cc2c(NC(=O)Nc3c(Cl)cccc3Cl)ncnc2cc1OCCCN1CCC(CN)CC1 | null | null | C(Cl)(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(Nc1ccccc1)Nc1ncnc2cc(OCCCN3CCCCC3)ccc12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 58.6 | [{"value": 58.6, "product": "NCC1CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)NC(=O)NC1=C(C=CC=C1Cl)Cl)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 40 | MINUTE | A mixture of 1-{7-[3-(4-tert-butoxycarbonylaminomethylpiperidin-1-yl)propoxy]-6-methoxyquinazolin-4-yl}-3-(2,6-dichlorophenyl)urea (0.075 g), trifluoroacetic acid (0.35 ml) and chloroform (1.5 ml) was stirred at ambient temperature for 40 minutes. The mixture was evaporated and the residue was stirred under a 1N aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HO- | C(Cl)(Cl)Cl | null | 0.666667 | COc1cc2c(NC(=O)Nc3c(Cl)cccc3Cl)ncnc2cc1OCCCN1CCC(CNC(=O)OC(C)(C)C)CC1>C(Cl)(Cl)Cl>COc1cc2c(NC(=O)Nc3c(Cl)cccc3Cl)ncnc2cc1OCCCN1CCC(CN)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b00c4a155d684d489c9cb91c53688a6e | COc1cc2c(NC(=O)Nc3c(C)cccc3C)ncnc2cc1OCCCN1CCC(CNC(=O)OC(C)(C)C)CC1>>COc1cc2c(NC(=O)Nc3c(C)cccc3C)ncnc2cc1OCCCN1CCC(CN)CC1 | C(C)(C)(C)OC(=O)NCC1CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)NC(=O)NC1=C(C=CC=C1C)C)OC.FC(C(=O)O)(F)F>>NCC1CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)NC(=O)NC1=C(C=CC=C1C)C)OC | CC(C)(C)OC(=O)[NH:34][CH2:33][CH:32]1[CH2:31][CH2:30][N:29]([CH2:28][CH2:27][CH2:26][O:25][c:24]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([NH:7][C:8](=[O:9])[NH:10][c:11]4[c:12]([CH3:13])[cH:14][cH:15][cH:16][c:17]4[CH3:18])[n:19][cH:20][n:21][c:22]3[cH:23]2)[CH2:36][CH2:35]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][C:8... | COc1cc2c(NC(=O)Nc3c(C)cccc3C)ncnc2cc1OCCCN1CCC(CNC(=O)OC(C)(C)C)CC1 | COc1cc2c(NC(=O)Nc3c(C)cccc3C)ncnc2cc1OCCCN1CCC(CN)CC1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(Nc1ccccc1)Nc1ncnc2cc(OCCCN3CCCCC3)ccc12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | Using an analogous procedure to that described in Example 21, 1-{7-[3-(4 tert-butoxycarbonylaminomethylpiperidin-1-yl)propoxy]-6-methoxyquinazolin-4-yl}-3-(2,6-dimethylphenyl)urea was reacted with trifluoroacetic acid to give the title compound; NMR Spectrum: (DMSOd6) 1.0-2.0 (m, 9H), 2.23 (s, 6H), 2.4 (m, 2H), 2.7-2.9... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HO- | null | null | null | COc1cc2c(NC(=O)Nc3c(C)cccc3C)ncnc2cc1OCCCN1CCC(CNC(=O)OC(C)(C)C)CC1>>COc1cc2c(NC(=O)Nc3c(C)cccc3C)ncnc2cc1OCCCN1CCC(CN)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-25debf80f27f40a4a5f9c837fb051e65 | COc1cc2c(NC(=O)Nc3c(C)cccc3Cl)ncnc2cc1OCCCN1CCC(CNC(=O)OC(C)(C)C)CC1>>COc1cc2c(NC(=O)Nc3c(C)cccc3Cl)ncnc2cc1OCCCN1CCC(CN)CC1 | C(C)(C)(C)OC(=O)NCC1CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)NC(=O)NC1=C(C=CC=C1C)Cl)OC.FC(C(=O)O)(F)F>>NCC1CCN(CC1)CCCOC1=C(C=C2C(=NC=NC2=C1)NC(=O)NC1=C(C=CC=C1C)Cl)OC | CC(C)(C)OC(=O)[NH:34][CH2:33][CH:32]1[CH2:31][CH2:30][N:29]([CH2:28][CH2:27][CH2:26][O:25][c:24]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([NH:7][C:8](=[O:9])[NH:10][c:11]4[c:12]([CH3:13])[cH:14][cH:15][cH:16][c:17]4[Cl:18])[n:19][cH:20][n:21][c:22]3[cH:23]2)[CH2:36][CH2:35]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][C:8]... | COc1cc2c(NC(=O)Nc3c(C)cccc3Cl)ncnc2cc1OCCCN1CCC(CNC(=O)OC(C)(C)C)CC1 | COc1cc2c(NC(=O)Nc3c(C)cccc3Cl)ncnc2cc1OCCCN1CCC(CN)CC1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(Nc1ccccc1)Nc1ncnc2cc(OCCCN3CCCCC3)ccc12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | Using an analogous procedure to that described in Example 21, 1-{7-[3-(4-tert-butoxycarbonylaminomethylpiperidin-1-yl)propoxy]-6-methoxyquinazolin-4-yl}-3-(2-chloro-6-methylphenyl)urea was reacted with trifluoroacetic acid to give the title compound; NMR Spectrum: (DMSOd6) 1.0-1.3 (m, 3H), 1.63 (d, 2H), 1.7-2.0 (m, 4H)... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HO- | null | null | null | COc1cc2c(NC(=O)Nc3c(C)cccc3Cl)ncnc2cc1OCCCN1CCC(CNC(=O)OC(C)(C)C)CC1>>COc1cc2c(NC(=O)Nc3c(C)cccc3Cl)ncnc2cc1OCCCN1CCC(CN)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-02e849ec93334d6dbdb5ddfd59d5f96a | COc1cc2c(N)ncnc2cc1OCC1CCN(C)CC1.Cc1cccc(C)c1N=C=S>>COc1cc2c(NC(=S)Nc3c(C)cccc3C)ncnc2cc1OCC1CCN(C)CC1 | CC1=C(C(=CC=C1)C)N=C=S.NC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C.[H-].[Na+]>>CC1=C(C(=CC=C1)C)NC(=S)NC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH2:7])[n:19][cH:20][n:21][c:22]2[cH:23][c:24]1[O:25][CH2:26][CH:27]1[CH2:28][CH2:29][N:30]([CH3:31])[CH2:32][CH2:33]1.[C:8](=[S:9])=[N:10][c:11]1[c:12]([CH3:13])[cH:14][cH:15][cH:16][c:17]1[CH3:18]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][C:8](=[S:9])[NH:10][c:11]3[c:12]([CH3:13... | COc1cc2c(N)ncnc2cc1OCC1CCN(C)CC1.Cc1cccc(C)c1N=C=S | COc1cc2c(NC(=S)Nc3c(C)cccc3C)ncnc2cc1OCC1CCN(C)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | thiourea | 9037f368cdf8e91fcd9f93f4d9cf27991f85fa921c9d19c7875d3a77561f439b | 0fbf3d6c8cd704ac451c2cf111f32090de5e76a9d41cce326e212c758f4ed46f | S=C(Nc1ccccc1)Nc1ncnc2cc(OCC3CCNCC3)ccc12 | [NH2;D1;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[S;D1;H0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[S;D1;H0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13])-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1 | 48.5 | [{"value": 48.5, "product": "CC1=C(C(=CC=C1)C)NC(=S)NC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A solution of 4-amino-6-methoxy-7-(1-methylpiperidin-4-ylmethoxy)quinazoline (150 mg) in DMF (4.5 ml) was added to sodium hydride (60% dispersion in mineral oil, 0.03 g) and the reaction mixture was stirred at ambient temperature for 20 minutes. 2,6-Dimethylphenyl isothiocyanate (0.162 g) was added and the mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Isothiocyanate | Thiourea | null | null | c1ccccc1.c1ccc2ncncc2c1.C1CC[NH]CC1 | null | CN(C)C=O | null | 0.333333 | COc1cc2c(N)ncnc2cc1OCC1CCN(C)CC1.Cc1cccc(C)c1N=C=S>CN(C)C=O>COc1cc2c(NC(=S)Nc3c(C)cccc3C)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bf683cd41b1c4328b10081e0ffda2ddb | COc1cc2c(NC(=S)Nc3c(C)cccc3C)ncnc2cc1OCC1CCN(C)CC1.N>>COc1cc2c(NC(=N)Nc3c(C)cccc3C)ncnc2cc1OCC1CCN(C)CC1 | N.CC1=C(C(=CC=C1)C)NC(=S)NC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C>>CC1=C(C(=CC=C1)C)NC(=N)NC1=NC=NC2=CC(=C(C=C12)OC)OCC1CCN(CC1)C | S=[C:8]([NH:7][c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][CH:27]3[CH2:28][CH2:29][N:30]([CH3:31])[CH2:32][CH2:33]3)[cH:23][c:22]2[n:21][cH:20][n:19]1)[NH:10][c:11]1[c:12]([CH3:13])[cH:14][cH:15][cH:16][c:17]1[CH3:18].[NH3:9]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][C:8](=[NH:9])[NH:10][c:11]3[c:12]([C... | COc1cc2c(NC(=S)Nc3c(C)cccc3C)ncnc2cc1OCC1CCN(C)CC1.N | COc1cc2c(NC(=N)Nc3c(C)cccc3C)ncnc2cc1OCC1CCN(C)CC1 | null | null | C(Cl)(Cl)Cl.CO | Heteroatom Alkylation and Arylation | OtherReaction | 67487dbd2c9f26053eb28d881e99dd20bae147d196eb1e5bafcb5ffcf2e4e325 | 11b251af32763a68dad1ec379720724b0b8f9520bc1c6c42378972cb96f53737 | N=C(Nc1ccccc1)Nc1ncnc2cc(OCC3CCNCC3)ccc12 | S=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[#7:4]-[c:5]:[#7;a:6].[NH3;D0;+0:7]>>[#7;a:6]:[c:5]-[#7:4]-[C;H0;D3;+0:1](=[NH;D1;+0:7])-[#7:2]-[c:3] | null | [] | null | null | null | null | Mercuric(II) oxide (0.059 g) was added to a mixture of 1-(2,6-dimethylphenyl)-3-[6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazolin-4-yl]thiourea (0.105 g), a 2M solution of ammonia in methanol (3 ml) and chloroform (1 ml) and the reaction mixture was stirred at ambient temperature for 2 hours. The mixture was evapo... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea | null | null | null | c1ccccc1.c1ccc2ncncc2c1.C1CC[NH]CC1 | Other | C(Cl)(Cl)Cl.CO | null | null | COc1cc2c(NC(=S)Nc3c(C)cccc3C)ncnc2cc1OCC1CCN(C)CC1.N>C(Cl)(Cl)Cl.CO>COc1cc2c(NC(=N)Nc3c(C)cccc3C)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e172c35e48a74f4d96107398c48503f1 | COc1cc2c(NC(=S)N[C@H](C)c3ccccc3)ncnc2cc1OCC1CCN(C)CC1.N>>COc1cc2c(NC(=N)N[C@H](C)c3ccccc3)ncnc2cc1OCC1CCN(C)CC1 | COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)NC(=S)N[C@@H](C1=CC=CC=C1)C.N>>COC=1C=C2C(=NC=NC2=CC1OCC1CCN(CC1)C)NC(=N)N[C@@H](C1=CC=CC=C1)C | S=[C:8]([NH:7][c:6]1[c:5]2[cH:4][c:3]([O:2][CH3:1])[c:24]([O:25][CH2:26][CH:27]3[CH2:28][CH2:29][N:30]([CH3:31])[CH2:32][CH2:33]3)[cH:23][c:22]2[n:21][cH:20][n:19]1)[NH:10][C@H:11]([CH3:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[NH3:9]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([NH:7][C:8](=[NH:9])[NH:10][C@H:11]([CH3:... | COc1cc2c(NC(=S)N[C@H](C)c3ccccc3)ncnc2cc1OCC1CCN(C)CC1.N | COc1cc2c(NC(=N)N[C@H](C)c3ccccc3)ncnc2cc1OCC1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 67487dbd2c9f26053eb28d881e99dd20bae147d196eb1e5bafcb5ffcf2e4e325 | 11b251af32763a68dad1ec379720724b0b8f9520bc1c6c42378972cb96f53737 | N=C(NCc1ccccc1)Nc1ncnc2cc(OCC3CCNCC3)ccc12 | S=[C;H0;D3;+0:1](-[#7:2]-[C:3])-[#7:4]-[c:5]:[#7;a:6].[NH3;D0;+0:7]>>[#7;a:6]:[c:5]-[#7:4]-[C;H0;D3;+0:1](=[NH;D1;+0:7])-[#7:2]-[C:3] | null | [] | null | null | null | null | Using an analogous procedure to that described in Example 29, 1 [6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazolin-4-yl]-3-[(R)-(+)-α-methylbenzyl]thiourea was reacted with ammonia to give the title compound; NMR Spectrum: (CDCl3)1.38-1.42 (m, 2H), 1.61 (d, 3H), 1.86-2.01 (q, 5H), 2.29 (s, 3H), 2.89 (d, 2H), 3.95 (... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea | null | null | null | c1ccccc1.c1ccc2ncncc2c1.C1CC[NH]CC1 | Other | null | null | null | COc1cc2c(NC(=S)N[C@H](C)c3ccccc3)ncnc2cc1OCC1CCN(C)CC1.N>>COc1cc2c(NC(=N)N[C@H](C)c3ccccc3)ncnc2cc1OCC1CCN(C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e167641bb4ba41f38ad99a7e66918a01 | COc1cc2ncnc(NC(=O)Nc3ccccc3[N+](=O)[O-])c2cc1OC>>COc1cc2ncnc(NC(=O)Nc3ccccc3N)c2cc1OC | COC=1C=C2C(=NC=NC2=CC1OC)NC(=O)NC1=C(C=CC=C1)[N+](=O)[O-]>>NC1=C(C=CC=C1)NC(=O)NC1=NC=NC2=CC(=C(C=C12)OC)OC | O=[N+:20]([O-])[c:19]1[c:14]([NH:13][C:11]([NH:10][c:9]2[n:8][cH:7][n:6][c:5]3[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH3:25])[cH:22][c:21]32)=[O:12])[cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([NH:10][C:11](=[O:12])[NH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[NH2:20])[c:21]2[... | COc1cc2ncnc(NC(=O)Nc3ccccc3[N+](=O)[O-])c2cc1OC | COc1cc2ncnc(NC(=O)Nc3ccccc3N)c2cc1OC | null | [Pd] | CN(C)C=O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(Nc1ccccc1)Nc1ncnc2ccccc12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 82.8 | [{"value": 62.0, "product": "NC1=C(C=CC=C1)NC(=O)NC1=NC=NC2=CC(=C(C=C12)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.8, "product": "NC1=C(C=CC=C1)NC(=O)NC1=NC=NC2=CC(=C(C=C12)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture of 1-(6,7dimethoxyquinazolin-4-yl)-3-(2-nitrophenyl)urea (0.18 g), 10% palladium charcoal catalyst (0.023 g) and DMF (10 ml) was stirred at ambient temperature under an atmosphere of hydrogen for 16 hours. The reaction mixture was filtered and the filtrate was evaporated. The resultant gum was triturated unde... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncncc2c1.c1ccccc1 | Other | [Pd].CN(C)C=O | null | 16 | COc1cc2ncnc(NC(=O)Nc3ccccc3[N+](=O)[O-])c2cc1OC>[Pd].CN(C)C=O>COc1cc2ncnc(NC(=O)Nc3ccccc3N)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-66c741410bb345ed9d80b0aae8b6e2b4 | CC(=O)OC(C)=O.O=C1O[C@@H](CO)CN1c1cccc(F)c1>>CC(=O)OC[C@H]1CN(c2cccc(F)c2)C(=O)O1 | C([O-])(O)=O.[Na+].FC=1C=C(C=CC1)N1C(O[C@H](C1)CO)=O.C(C)N(CC)CC.C(C)(=O)OC(C)=O>>FC=1C=C(C=CC1)N1C(O[C@H](C1)COC(C)=O)=O | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][c:13]([F:14])[cH:15]2)[C:16](=[O:17])[O:18]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][c:13]([F:14])[cH:15]2)[C:16](=[O:17])[O:18]1 | CC(=O)OC(C)=O.O=C1O[C@@H](CO)CN1c1cccc(F)c1 | CC(=O)OC[C@H]1CN(c2cccc(F)c2)C(=O)O1 | null | CN(C1=CC=NC=C1)C | ClCCl | Acylation | Transesterification | f81e513b7b512b10157c16426844efd8d88e34c97987c1347c6ba8a688351205 | fc27d67c790d5fb520ba5d49de1490661fa5b822b714863734ce7e3029dfa84f | O=C1OCCN1c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#8:4]-[C:5]-[C:6]-[OH;D1;+0:7]>>[#8:4]-[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 103.4 | [{"value": 103.4, "product": "FC=1C=C(C=CC1)N1C(O[C@H](C1)COC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | (5R)-3-(3-Fluorophenyl)-5-hydroxymethyl-1,3-oxazolidin-2-one (40 g, 0.189 M, see Upjohn WO 94-13649) was suspended by stirring in dry dichloromethane (400 mL) under nitrogen. Triethylamine (21 g, 0.208 M) and 4-dimethylaminopyridine (0.6 g, 4.9 mM) were added, followed by dropwise addition of acetic anhydride (20.3 g, ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol | Ester | null | null | C1COC[NH]1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.ClCCl | null | 18 | CC(=O)OC(C)=O.O=C1O[C@@H](CO)CN1c1cccc(F)c1>CN(C1=CC=NC=C1)C.ClCCl>CC(=O)OC[C@H]1CN(c2cccc(F)c2)C(=O)O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee34cd29f312461fa512c3186f3f44bd | CC(=O)OC[C@H]1CN(c2cccc(F)c2)C(=O)O1.II>>CC(=O)OC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1 | FC=1C=C(C=CC1)N1C(O[C@H](C1)COC(C)=O)=O.II>>FC=1C=C(C=CC1I)N1C(O[C@H](C1)COC(C)=O)=O | [CH3:1][C:2](=[O:3])[O:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][c:14]([F:15])[cH:16]2)[C:17](=[O:18])[O:19]1.I[I:13]>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([I:13])[c:14]([F:15])[cH:16]2)[C:17](=[O:18])[O:19]1 | CC(=O)OC[C@H]1CN(c2cccc(F)c2)C(=O)O1.II | CC(=O)OC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1 | null | FC(C(=O)[O-])(F)F.[Ag+].FC(C(=O)[O-])(F)F.[Ag+] | C(C)#N.C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C1OCCN1c1ccccc1 | I-[I;H0;D1;+0:1].[F;D1;H0:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[F;D1;H0:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[I;H0;D1;+0:1]):[c:6]:[c:7] | 106.8 | [{"value": 106.8, "product": "FC=1C=C(C=CC1I)N1C(O[C@H](C1)COC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | Acetic acid (5R)-3-(3-fluoro-phenyl)-1,3-oxazolidin-2-one-5-ylmethyl ester (15.2 g, 60 mM) was dissolved in a mixture of chloroform (100 mL) and acetonitrile (100 mL) under nitrogen, and silver trifluoroacetate (16.96 g, 77 mM) added. Iodine (18.07 g, 71 mM) was added in portions over 30 minutes to the vigorously stirr... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | C1COC[NH]1.c1ccccc1 | HI | FC(C(=O)[O-])(F)F.[Ag+].FC(C(=O)[O-])(F)F.[Ag+].C(C)#N.C(Cl)(Cl)Cl | null | 18 | CC(=O)OC[C@H]1CN(c2cccc(F)c2)C(=O)O1.II>FC(C(=O)[O-])(F)F.[Ag+].FC(C(=O)[O-])(F)F.[Ag+].C(C)#N.C(Cl)(Cl)Cl>CC(=O)OC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cee389fc35a04b8abdd2408ebd5e3784 | CC(=O)OC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1>>O=C1O[C@@H](CO)CN1c1ccc(I)c(F)c1 | FC=1C=C(C=CC1I)N1C(O[C@H](C1)COC(C)=O)=O.C([O-])([O-])=O.[K+].[K+].C(C)(=O)O.O>>FC=1C=C(C=CC1I)N1C(O[C@H](C1)CO)=O | CC(=O)[O:6][CH2:5][C@@H:4]1[O:3][C:2](=[O:1])[N:8]([c:9]2[cH:10][cH:11][c:12]([I:13])[c:14]([F:15])[cH:16]2)[CH2:7]1>>[O:1]=[C:2]1[O:3][C@@H:4]([CH2:5][OH:6])[CH2:7][N:8]1[c:9]1[cH:10][cH:11][c:12]([I:13])[c:14]([F:15])[cH:16]1 | CC(=O)OC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1 | O=C1O[C@@H](CO)CN1c1ccc(I)c(F)c1 | null | null | ClCCl.CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | O=C1OCCN1c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]-[#8:4]>>[#8:4]-[C:3]-[C:2]-[OH;D1;+0:1] | 86.2 | [{"value": 86.2, "product": "FC=1C=C(C=CC1I)N1C(O[C@H](C1)CO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Acetic acid (5R)-3-(3-fluoro-4-iodophenyl)-1,3-oxazolidin-2-one-5-ylmethyl ester (30 g, 79 mM) was treated with potassium carbonate (16.4 g, 0.119 mM) in a mixture of methanol (800 mL) and dichloromethane (240 mL) at ambient temperature for 25 minutes, then immediately neutralised by the addition of acetic acid (10 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1COC[NH]1.c1ccccc1 | HO- | ClCCl.CO | null | null | CC(=O)OC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1>ClCCl.CO>O=C1O[C@@H](CO)CN1c1ccc(I)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-746a69381cb548acbfa33ab1d8bdb906 | Brc1ccc(Br)nc1>>N#Cc1ccc(Br)cn1 | C(C)(=O)OCC.[OH-].[Na+].BrC1=NC=C(C=C1)Br.C(#N)[Cu]>>BrC=1C=NC(=CC1)C#N | Br[c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][n:9]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][n:9]1 | Brc1ccc(Br)nc1 | N#Cc1ccc(Br)cn1 | null | null | CN1CCCC1=O | Miscellaneous | OtherReaction | 8bb970223fb9058022a1c0cc1f9e538de973681a8f3a5dcbab2e4e1d78c06c44 | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccncc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]>>[N;D1;H0:6]#[C:7]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 28 | [{"value": 28.0, "product": "BrC=1C=NC(=CC1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.4, "product": "BrC=1C=NC(=CC1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 1 | HOUR | A stirred solution of 2,5-dibromopyridine (39.465 g, 0.17 mol) in anhydrous NMP (100 mL) was treated with CuCN (14.42 g, 0.17 mol) for 20 hours at 110° C. under nitrogen. The reaction mixture was cooled to 40° C. and treated with aqueous sodium hydroxide (2M; 200 mL) and then with ethyl acetate (200 mL). The mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccncc1 | c1ccncc1 | c1ccncc1 | Br- | CN1CCCC1=O | 40 | 1 | Brc1ccc(Br)nc1>CN1CCCC1=O>N#Cc1ccc(Br)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f08ba27cbfad482bb60f59a43d1dedba | N#Cc1ccc(Br)cn1.[N-]=[N+]=[N-]>>Brc1ccc(-c2nnn[nH]2)nc1 | BrC=1C=NC(=CC1)C#N.[N-]=[N+]=[N-].[Na+].[Cl-].[NH4+]>>BrC=1C=CC(=NC1)C1=NN=NN1 | [Br:1][c:2]1[cH:3][cH:4][c:5]([C:6]#[N:7])[n:11][cH:12]1.[N+:8](=[N-:9])=[N-:10]>>[Br:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8][n:9][nH:10]2)[n:11][cH:12]1 | N#Cc1ccc(Br)cn1.[N-]=[N+]=[N-] | Brc1ccc(-c2nnn[nH]2)nc1 | null | null | CN(C=O)C.C(C)(=O)OCC | Aromatic Heterocycle Formation | OtherReaction | 237b84aaa459abf427f233dc6a07a1d9de824f980714e458423189bb68f60f12 | d8c808528b7ee68720aaeebd35cb6a2a30e344748d0066102cdae99843b93cf0 | c1ccc(-c2nnn[nH]2)nc1 | [N-;H0;D1:1]=[N+;H0;D2:2]=[N-;H0;D1:3].[N;H0;D1;+0:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[#7;a:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:2]:[n;H0;D2;+0:3]:[nH;D2;+0:1]:1):[c:9]:[c:10] | null | [] | 120 | CELSIUS | null | null | A mixture of 3-bromo-6-cyano-pyridine (2 g, 10.9 mmol), sodium azide (0.85 g, 13 mmol), and ammonium chloride (0.59 g, 11 mmol) in N,N-dimethylformamide (20 mL) was heated for 1 h at 120° C. The reaction mixture was diluted with ethyl acetate (˜100 mL) and the product was isolated by filtration and then washed with eth... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | null | c1nnn[nH]1 | c1ccncc1.c1nnn[nH]1 | null | CN(C=O)C.C(C)(=O)OCC | 120 | null | N#Cc1ccc(Br)cn1.[N-]=[N+]=[N-]>CN(C=O)C.C(C)(=O)OCC>Brc1ccc(-c2nnn[nH]2)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6eb85ba576714ed78d7c0c2108d5cfa0 | C#CCO.[N-]=[N+]=NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1>>O=C1O[C@@H](Cn2cc(CO)nn2)CN1c1ccc(I)c(F)c1 | FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN=[N+]=[N-])=O.C(C#C)O>>FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN1N=NC(=C1)CO)=O | [CH:7]#[C:8][CH2:9][OH:10].[O:1]=[C:2]1[O:3][C@@H:4]([CH2:5][N:6]=[N+:12]=[N-:11])[CH2:13][N:14]1[c:15]1[cH:16][cH:17][c:18]([I:19])[c:20]([F:21])[cH:22]1>>[O:1]=[C:2]1[O:3][C@@H:4]([CH2:5][n:6]2[cH:7][c:8]([CH2:9][OH:10])[n:11][n:12]2)[CH2:13][N:14]1[c:15]1[cH:16][cH:17][c:18]([I:19])[c:20]([F:21])[cH:22]1 | C#CCO.[N-]=[N+]=NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1 | O=C1O[C@@H](Cn2cc(CO)nn2)CN1c1ccc(I)c(F)c1 | null | [Cu]I | C(C)#N | Aromatic Heterocycle Formation | Huisgen alkyne-azide 1,3 dipolar cycloaddition | 5fc85c7d5248d7441d4bc0614ca3ab351489100bea35d1544b87c09cc52684b2 | 1b28a956951e72cdb4476ce5c3f0edc31c5e777adf082b56541e25aaf43aafaa | O=C1O[C@@H](Cn2ccnn2)CN1c1ccccc1 | [#8:1]-[C:2]-[C:3]-[N;H0;D2;+0:4]=[N+;H0;D2:5]=[N-;H0;D1:6].[CH;D1;+0:7]#[C;H0;D2;+0:8]-[C:9]-[O;D1;H1:10]>>[#8:1]-[C:2]-[C:3]-[n;H0;D3;+0:4]1:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[C:9]-[O;D1;H1:10]):[n;H0;D2;+0:6]:[n;H0;D2;+0:5]:1 | null | [] | null | null | 8 | HOUR | A mixture of (5R)-3-(3-fluoro-4-iodophenyl)-5-azidomethyl-1,3-oxazolidin-2-one (10 g, 28 mmol) and propargyl alcohol (3.2 mL, 56 mmol) in acetonitrile (80 mL) was treated with CuI (526 mg, 2.8 mmol) and then stirred overnight. The solidified reaction mixture was extracted with ethyl acetate:acetonitrile, washed with wa... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Alkyne | null | null | c1c[nH]nn1 | C1COC[NH]1.c1c[nH]nn1.c1ccccc1 | null | [Cu]I.C(C)#N | null | 8 | C#CCO.[N-]=[N+]=NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1>[Cu]I.C(C)#N>O=C1O[C@@H](Cn2cc(CO)nn2)CN1c1ccc(I)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cc09253487134a2a96f2d75154486a18 | BrC(Br)(Br)Br.O=C1O[C@@H](Cn2cc(CO)nn2)CN1c1ccc(I)c(F)c1>>O=C1O[C@@H](Cn2cc(CBr)nn2)CN1c1ccc(I)c(F)c1 | FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN1N=NC(=C1)CO)=O.C(Br)(Br)(Br)Br.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN1N=NC(=C1)CBr)=O | BrC(Br)(Br)[Br:10].O[CH2:9][c:8]1[cH:7][n:6]([CH2:5][C@@H:4]2[O:3][C:2](=[O:1])[N:14]([c:15]3[cH:16][cH:17][c:18]([I:19])[c:20]([F:21])[cH:22]3)[CH2:13]2)[n:12][n:11]1>>[O:1]=[C:2]1[O:3][C@@H:4]([CH2:5][n:6]2[cH:7][c:8]([CH2:9][Br:10])[n:11][n:12]2)[CH2:13][N:14]1[c:15]1[cH:16][cH:17][c:18]([I:19])[c:20]([F:21])[cH:22]... | BrC(Br)(Br)Br.O=C1O[C@@H](Cn2cc(CO)nn2)CN1c1ccc(I)c(F)c1 | O=C1O[C@@H](Cn2cc(CBr)nn2)CN1c1ccc(I)c(F)c1 | null | null | ClCCl | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | O=C1O[C@@H](Cn2ccnn2)CN1c1ccccc1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3]1:[#7;a:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[#7;a:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1 | 82.9 | [{"value": 82.9, "product": "FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN1N=NC(=C1)CBr)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | A stirred mixture of (5R)-3-(3-fluoro-4-iodophenyl)-5-(4-hydroxymethyl-1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (14.7 g, 35.1 mmol) and carbon tetrabromide (12.16 g, 36.7 mmol) in dichloromethane (1 L) was treated at 0° C. with triphenylphosphine (12.34 g, 61.2 mmol). The reaction mixture was stirred for 30 mi... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | C1COC[NH]1.c1c[nH]nn1.c1ccccc1 | HBr | ClCCl | 0 | 0.5 | BrC(Br)(Br)Br.O=C1O[C@@H](Cn2cc(CO)nn2)CN1c1ccc(I)c(F)c1>ClCCl>O=C1O[C@@H](Cn2cc(CBr)nn2)CN1c1ccc(I)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e5a205cdfd484f17b3e7fe7aacf8f026 | O=C1O[C@@H](Cn2cc(CBr)nn2)CN1c1ccc(I)c(F)c1.[F-]>>O=C1O[C@@H](Cn2cc(CF)nn2)CN1c1ccc(I)c(F)c1 | FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN1N=NC(=C1)CBr)=O.[F-].[K+].F[B-](F)(F)F.C(CCC)[N+]1=CN(C=C1)C>>FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN1N=NC(=C1)CF)=O | Br[CH2:9][c:8]1[cH:7][n:6]([CH2:5][C@@H:4]2[O:3][C:2](=[O:1])[N:14]([c:15]3[cH:16][cH:17][c:18]([I:19])[c:20]([F:21])[cH:22]3)[CH2:13]2)[n:12][n:11]1.[F-:10]>>[O:1]=[C:2]1[O:3][C@@H:4]([CH2:5][n:6]2[cH:7][c:8]([CH2:9][F:10])[n:11][n:12]2)[CH2:13][N:14]1[c:15]1[cH:16][cH:17][c:18]([I:19])[c:20]([F:21])[cH:22]1 | O=C1O[C@@H](Cn2cc(CBr)nn2)CN1c1ccc(I)c(F)c1.[F-] | O=C1O[C@@H](Cn2cc(CF)nn2)CN1c1ccc(I)c(F)c1 | null | null | C(C)#N.O.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | e944a2acb95a43a23818321f2ac2f96ba2f2b8d34f52c1cfd1e3802d2403177f | e2ca6f9fe1078a3836d617896a4e5cc310fb155ca459b021e2b549b3e61f1df7 | O=C1O[C@@H](Cn2ccnn2)CN1c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[#7;a:5](-[C:6]):[c:7]:1.[F-;H0;D0:8]>>[C:6]-[#7;a:5]1:[#7;a:4]:[#7;a:3]:[c:2](-[CH2;D2;+0:1]-[F;H0;D1;+0:8]):[c:7]:1 | 45 | [{"value": 45.0, "product": "FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN1N=NC(=C1)CF)=O", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A mixture of (5R)-3-(3-fluoro-4-iodophenyl)-5-(4-bromomethyl-1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (6.94 g, 14.4 mmol), potassium fluoride (4.19 g, 72.1 mmol), and 1-butyl-3-methylimidazolium tetrafluoroborate (18.4 mL) in acetonitrile (250 mL) and water (1.5 mL) was heated to 90° C. overnight. The reaction... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary halide | null | null | C1COC[NH]1.c1c[nH]nn1.c1ccccc1 | Br- | C(C)#N.O.C(C)(=O)OCC | 90 | null | O=C1O[C@@H](Cn2cc(CBr)nn2)CN1c1ccc(I)c(F)c1.[F-]>C(C)#N.O.C(C)(=O)OCC>O=C1O[C@@H](Cn2cc(CF)nn2)CN1c1ccc(I)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2bd0a83fae8045caac887b4543fd26f6 | CC1(C)OB(c2ccc(N3C[C@H](Cn4cc(Cl)nn4)OC3=O)cc2F)OC1(C)C.Cn1nnc(-c2ccc(Br)cn2)n1>>Cn1nnc(-c2ccc(-c3ccc(N4C[C@H](Cn5cc(Cl)nn5)OC4=O)cc3F)cn2)n1 | FC=1C=C(C=CC1B1OC(C(O1)(C)C)(C)C)N1C(O[C@H](C1)CN1N=NC(=C1)Cl)=O.BrC=1C=CC(=NC1)C=1N=NN(N1)C.C([O-])([O-])=O.[Na+].[Na+]>>FC=1C=C(C=CC1C=1C=NC(=CC1)C=1N=NN(N1)C)N1C(O[C@H](C1)CN1N=NC(=C1)Cl)=O | CC1(C)OB([c:10]2[cH:11][cH:12][c:13]([N:14]3[CH2:15][C@H:16]([CH2:17][n:18]4[cH:19][c:20]([Cl:21])[n:22][n:23]4)[O:24][C:25]3=[O:26])[cH:27][c:28]2[F:29])OC1(C)C.Br[c:9]1[cH:8][cH:7][c:6](-[c:5]2[n:4][n:3][n:2]([CH3:1])[n:32]2)[n:31][cH:30]1>>[CH3:1][n:2]1[n:3][n:4][c:5](-[c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11][cH:12][... | CC1(C)OB(c2ccc(N3C[C@H](Cn4cc(Cl)nn4)OC3=O)cc2F)OC1(C)C.Cn1nnc(-c2ccc(Br)cn2)n1 | Cn1nnc(-c2ccc(-c3ccc(N4C[C@H](Cn5cc(Cl)nn5)OC4=O)cc3F)cn2)n1 | null | null | CN(C=O)C | C-C Coupling | Suzuki coupling with boronic esters | 41faa5d7c8b2fa5e7977311a48e89454061b096772c8348f0e02516e76bb87f9 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | O=C1O[C@@H](Cn2ccnn2)CN1c1ccc(-c2ccc(-c3nn[nH]n3)nc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.C-C1(-C)-O-B(-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[F;D1;H0:11]):[c:12])-O-C-1(-C)-C>>[F;D1;H0:11]-[c:10](:[c:12]):[c;H0;D3;+0:7](-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1):[c:8]:[c:9] | null | [] | 70 | CELSIUS | null | null | A mixture of (5R)-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5-(4-chloro-1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (300 mg, 0.71 mmol), 5-bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine (170 mg, 0.71 mmol), and sodium carbonate (226 mg, 2.13 mmol) in N,N-dimethylformamide:water (5 mL, 10:1) ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccccc1.c1ccncc1 | c1ccncc1.c1ccccc1 | c1nnn[nH]1.c1ccncc1.c1ccccc1.C1COC[NH]1.c1c[nH]nn1 | HBr.B | CN(C=O)C | 70 | null | CC1(C)OB(c2ccc(N3C[C@H](Cn4cc(Cl)nn4)OC3=O)cc2F)OC1(C)C.Cn1nnc(-c2ccc(Br)cn2)n1>CN(C=O)C>Cn1nnc(-c2ccc(-c3ccc(N4C[C@H](Cn5cc(Cl)nn5)OC4=O)cc3F)cn2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-edac06a9f1bc42bead9591b4140e9181 | C=C(Cl)S(=O)(=O)Cl.[N-]=[N+]=NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1>>O=C1O[C@@H](Cn2cc(Cl)nn2)CN1c1ccc(I)c(F)c1 | FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN=[N+]=[N-])=O.ClC(=C)S(=O)(=O)Cl>>FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN1N=NC(=C1)Cl)=O | O=S(=O)(Cl)[C:8](=[CH2:7])[Cl:9].[O:1]=[C:2]1[O:3][C@@H:4]([CH2:5][N:6]=[N+:11]=[N-:10])[CH2:12][N:13]1[c:14]1[cH:15][cH:16][c:17]([I:18])[c:19]([F:20])[cH:21]1>>[O:1]=[C:2]1[O:3][C@@H:4]([CH2:5][n:6]2[cH:7][c:8]([Cl:9])[n:10][n:11]2)[CH2:12][N:13]1[c:14]1[cH:15][cH:16][c:17]([I:18])[c:19]([F:20])[cH:21]1 | C=C(Cl)S(=O)(=O)Cl.[N-]=[N+]=NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1 | O=C1O[C@@H](Cn2cc(Cl)nn2)CN1c1ccc(I)c(F)c1 | null | null | C(Cl)(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | bf30c78864c31013065fc8fc6af6ff0137a2436a6cb6eaa922765cbe186b7d1a | 426729057b3d9c007d75726a9dac854572b7675fee89d339100a3b522fc787c6 | O=C1O[C@@H](Cn2ccnn2)CN1c1ccccc1 | Cl-S(=O)(=O)-[C;H0;D3;+0:1](=[CH2;D1;+0:2])-[Cl;D1;H0:3].[#8:4]-[C:5]-[C:6]-[N;H0;D2;+0:7]=[N+;H0;D2:8]=[N-;H0;D1:9]>>[#8:4]-[C:5]-[C:6]-[n;H0;D3;+0:7]1:[cH;D2;+0:2]:[c;H0;D3;+0:1](-[Cl;D1;H0:3]):[n;H0;D2;+0:9]:[n;H0;D2;+0:8]:1 | 62 | [{"value": 62.0, "product": "FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN1N=NC(=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.7, "product": "FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN1N=NC(=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A stirred mixture of (5R)-3-(3-fluoro-4-iodophenyl)-5-azidomethyl-1,3-oxazolidin-2-one (1 g, 28 mmol) and 1-chloro-1-ethenesulfonyl chloride (1 g, 6.2 mmol) was heated in a pressure tube at 80° C. for one hour. The reaction mixture was cooled to room temperature, diluted with chloroform (15 mL), and heated at 80° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Azide.Sulfonyl halide.Vinyl | Aromatic halide | null | c1c[nH]nn1 | C1COC[NH]1.c1c[nH]nn1.c1ccccc1 | HCl | C(Cl)(Cl)Cl | 80 | null | C=C(Cl)S(=O)(=O)Cl.[N-]=[N+]=NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1>C(Cl)(Cl)Cl>O=C1O[C@@H](Cn2cc(Cl)nn2)CN1c1ccc(I)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ec23d976acb4f869970ee250c87a048 | Cn1nnc(-c2ccc(Br)cn2)n1.O=C(OO)c1cccc(Cl)c1>>Cn1nnc(-c2ccc(Br)c[n+]2[O-])n1 | BrC=1C=CC(=NC1)C=1N=NN(N1)C.ClC1=CC(=CC=C1)C(=O)OO>>BrC=1C=CC(=[N+](C1)[O-])C=1N=NN(N1)C | [CH3:1][n:2]1[n:3][n:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][n:12]2)[n:14]1.O=C(O[OH:13])c1cccc(Cl)c1>>[CH3:1][n:2]1[n:3][n:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][n+:12]2[O-:13])[n:14]1 | Cn1nnc(-c2ccc(Br)cn2)n1.O=C(OO)c1cccc(Cl)c1 | Cn1nnc(-c2ccc(Br)c[n+]2[O-])n1 | null | null | ClCCCl | Miscellaneous | OtherReaction | 5b2b5a1eb88c9671c4a604b6f76054cc01cd86a1985fc147f7e56f19c4844d35 | 98b338a9d01476c0929fd5672e7509121bfe69600fd72e4d1cc6f1782e2d05d9 | c1ccc(-c2nn[nH]n2)[nH+]c1 | Cl-c1:c:c:c:c(-C(=O)-O-[OH;D1;+0:1]):c:1.[c:2]:[c:3](-[c:4]1:[#7;a:5]:[#7;a:6]:[#7;a:7]:[#7;a:8]:1):[n;H0;D2;+0:9]:[c:10]:[c:11]>>[O-;H0;D1:1]-[n+;H0;D3:9](:[c:10]:[c:11]):[c:3](-[c:4]1:[#7;a:5]:[#7;a:6]:[#7;a:7]:[#7;a:8]:1):[c:2] | null | [] | 80 | CELSIUS | null | null | 5-Bromo-2-(2-methyl-2H-tetrazol-5-yl)pyridine (175 mg, 0.73 mM) and 3-chloroperbenzoic acid (wet, 70%: 0.50 g, 2.05 mM) were dissolved in 1,2-dichloroethane (5 ml) and heated at 80° C. for 1.5 hours. The mixture was submitted directly to silica gel chromatography, eluting with 25% acetonitrile in dichloromethane. 5-Bro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Peroxide | null | c1ccncc1.c1ccccc1 | C1=CC=[NH+]C=C1 | c1nnn[nH]1.C1=CC=[NH+]C=C1 | HCl | ClCCCl | 80 | null | Cn1nnc(-c2ccc(Br)cn2)n1.O=C(OO)c1cccc(Cl)c1>ClCCCl>Cn1nnc(-c2ccc(Br)c[n+]2[O-])n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3f12a9403865430ba3903a2d8356e26d | Cn1nnc(-c2ccc(-c3ccc(N4C[C@H](Cn5ccnn5)OC4=O)cc3F)cn2)n1>>Cn1nnc(-c2ccc(-c3ccc(N4C[C@H](Cn5ccnn5)OC4=O)cc3F)c[n+]2[O-])n1 | [N+]1(=CC=CC=C1)[O-].C([O-])([O-])=O.[K+].[K+].FC=1C=C(C=CC1C=1C=NC(=CC1)C=1N=NN(N1)C)N1C(O[C@H](C1)CN1N=NC=C1)=O>>FC=1C=C(C=CC1C=1C=[N+](C(=CC1)C=1N=NN(N1)C)[O-])N1C(O[C@H](C1)CN1N=NC=C1)=O | [CH3:1][n:2]1[n:3][n:4][c:5](-[c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([N:14]4[CH2:15][C@H:16]([CH2:17][n:18]5[cH:19][cH:20][n:21][n:22]5)[O:23][C:24]4=[O:25])[cH:26][c:27]3[F:28])[cH:29][n:30]2)[n:32]1>>[CH3:1][n:2]1[n:3][n:4][c:5](-[c:6]2[cH:7][cH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([N:14]4[CH2:15][C@H:1... | Cn1nnc(-c2ccc(-c3ccc(N4C[C@H](Cn5ccnn5)OC4=O)cc3F)cn2)n1 | Cn1nnc(-c2ccc(-c3ccc(N4C[C@H](Cn5ccnn5)OC4=O)cc3F)c[n+]2[O-])n1 | null | C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)[Pd-4](P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | O.C1CCOC1 | Functional Group Interconversion | OtherReaction | 54415aed4bb61f76efee9ed140374352608210a9fed7c372975c12eb7023cea2 | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | O=C1O[C@@H](Cn2ccnn2)CN1c1ccc(-c2ccc(-c3nn[nH]n3)[nH+]c2)cc1 | [c:1]:[c:2](-[c:3]1:[#7;a:4]:[#7;a:5]:[#7;a:6]:[#7;a:7]:1):[n;H0;D2;+0:8]:[c:9]:[c:10]>>[O;-;D1;H0:11]-[n+;H0;D3:8](:[c:9]:[c:10]):[c:2](-[c:3]1:[#7;a:4]:[#7;a:5]:[#7;a:6]:[#7;a:7]:1):[c:1] | null | [] | 75 | CELSIUS | null | null | The above sample of pyridine oxide was combined with (5R)-3-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (335 mg, 0.86 mMol, prepared as in Example 1), potassium carbonate (400 mg, 2.9 mMol), and tetrakis(triphenylphosphino)palladium(0) (80 mg, 0.... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccncc1 | C1=CC=[NH+]C=C1 | c1nnn[nH]1.C1=CC=[NH+]C=C1.c1ccccc1.C1COC[NH]1.c1c[nH]nn1 | null | C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)[Pd-4](P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O.C1CCOC1 | 75 | null | Cn1nnc(-c2ccc(-c3ccc(N4C[C@H](Cn5ccnn5)OC4=O)cc3F)cn2)n1>C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)[Pd-4](P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O.C1CCOC1>Cn1nnc(-c2ccc(-c3ccc(N4C[C@H](Cn5ccnn5)OC4=O)cc3F)c[n+]2[O-])n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-be20d78bd782404d815629aba0e2d753 | Brc1ccc(-c2nn[nH]n2)nc1.OCCBr>>OCCn1nnc(-c2ccc(Br)cn2)n1 | BrCCO.[OH-].[K+].BrCCO.BrC=1C=CC(=NC1)C=1N=NNN1.[OH-].[K+].[OH-].[K+].BrCCO>>BrC=1C=CC(=NC1)C=1N=NN(N1)CCO | [nH:4]1[n:5][n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][n:14]2)[n:15]1.Br[CH2:3][CH2:2][OH:1]>>[OH:1][CH2:2][CH2:3][n:4]1[n:5][n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][n:14]2)[n:15]1 | Brc1ccc(-c2nn[nH]n2)nc1.OCCBr | OCCn1nnc(-c2ccc(Br)cn2)n1 | null | null | C(CC)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | d0dd3dd2b46bfd4f8f4e1b252548af601e8d30e74f99752eac7644d53f95dabe | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(-c2nn[nH]n2)nc1 | Br-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[#7;a:4]:[c:5]-[c:6]1:[#7;a:7]:[nH;D2;+0:8]:[#7;a:9]:[#7;a:10]:1>>[#7;a:4]:[c:5]-[c:6]1:[#7;a:7]:[n;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3]):[#7;a:9]:[#7;a:10]:1 | 26.4 | [{"value": 24.0, "product": "BrC=1C=CC(=NC1)C=1N=NN(N1)CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.4, "product": "BrC=1C=CC(=NC1)C=1N=NN(N1)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 5-Bromo-2-(2H-tetrazol-5-yl)pyridine (WO 0194342 A1) (1.2 g, 5.3 mmol) was dissolved/suspended in 1-propanol (15 ml), a solution of potassium hydroxide (250 mg, 4.5 mmol) in 1-propanol (15 ml) was added and it was heated at 80° C. for 1 hour. 2-Bromoethanol (0.344 ml, 4.8 mmol) was added and it was refluxed for one day... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1nnn[nH]1 | c1nnn[nH]1 | c1nnn[nH]1.c1ccncc1 | HBr | C(CC)O | 80 | null | Brc1ccc(-c2nn[nH]n2)nc1.OCCBr>C(CC)O>OCCn1nnc(-c2ccc(Br)cn2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5f65c6596ddf4a568c66f998d56c951f | O=C1O[C@@H](Cn2cc(CO)nn2)CN1c1ccc(I)c(F)c1>>O=Cc1cn(C[C@H]2CN(c3ccc(I)c(F)c3)C(=O)O2)nn1 | FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN1N=NC(=C1)CO)=O>>FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN1N=NC(=C1)C=O)=O | [OH:1][CH2:2][c:3]1[cH:4][n:5]([CH2:6][C@H:7]2[CH2:8][N:9]([c:10]3[cH:11][cH:12][c:13]([I:14])[c:15]([F:16])[cH:17]3)[C:18](=[O:19])[O:20]2)[n:21][n:22]1>>[O:1]=[CH:2][c:3]1[cH:4][n:5]([CH2:6][C@H:7]2[CH2:8][N:9]([c:10]3[cH:11][cH:12][c:13]([I:14])[c:15]([F:16])[cH:17]3)[C:18](=[O:19])[O:20]2)[n:21][n:22]1 | O=C1O[C@@H](Cn2cc(CO)nn2)CN1c1ccc(I)c(F)c1 | O=Cc1cn(C[C@H]2CN(c3ccc(I)c(F)c3)C(=O)O2)nn1 | null | [O-2].[Mn+2] | O1CCOCC1 | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | O=C1O[C@@H](Cn2ccnn2)CN1c1ccccc1 | [C:1]-[#7;a:2]1:[#7;a:3]:[#7;a:4]:[c:5](-[CH2;D2;+0:6]-[OH;D1;+0:7]):[c:8]:1>>[C:1]-[#7;a:2]1:[#7;a:3]:[#7;a:4]:[c:5](-[CH;D2;+0:6]=[O;H0;D1;+0:7]):[c:8]:1 | null | [] | 70 | CELSIUS | null | null | (5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-hydroxymethyl-1H-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one (5.7 g, 13.6 mmol) and manganese oxide (3.56 g, 40.9 mmol) were mixed and heated up to 100° C. in dry 1,4-dioxane for 48 hours, then the mixture was cooled down to 70° C. and filtered through celite. The filtrate was concen... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1c[nH]nn1.C1COC[NH]1.c1ccccc1 | null | [O-2].[Mn+2].O1CCOCC1 | 70 | null | O=C1O[C@@H](Cn2cc(CO)nn2)CN1c1ccc(I)c(F)c1>[O-2].[Mn+2].O1CCOCC1>O=Cc1cn(C[C@H]2CN(c3ccc(I)c(F)c3)C(=O)O2)nn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de891f7c262a4a0481ecf8d5394091e6 | C#CCO.[N-]=[N+]=NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1>>O=C1O[C@@H](Cn2cc(CO)nn2)CN1c1ccc(I)c(F)c1 | FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN=[N+]=[N-])=O.C(C#C)O>>FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN1N=NC(=C1)CO)=O | [CH:7]#[C:8][CH2:9][OH:10].[O:1]=[C:2]1[O:3][C@@H:4]([CH2:5][N:6]=[N+:12]=[N-:11])[CH2:13][N:14]1[c:15]1[cH:16][cH:17][c:18]([I:19])[c:20]([F:21])[cH:22]1>>[O:1]=[C:2]1[O:3][C@@H:4]([CH2:5][n:6]2[cH:7][c:8]([CH2:9][OH:10])[n:11][n:12]2)[CH2:13][N:14]1[c:15]1[cH:16][cH:17][c:18]([I:19])[c:20]([F:21])[cH:22]1 | C#CCO.[N-]=[N+]=NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1 | O=C1O[C@@H](Cn2cc(CO)nn2)CN1c1ccc(I)c(F)c1 | null | [Cu]I | C(C)#N | Aromatic Heterocycle Formation | Huisgen alkyne-azide 1,3 dipolar cycloaddition | 5fc85c7d5248d7441d4bc0614ca3ab351489100bea35d1544b87c09cc52684b2 | 1b28a956951e72cdb4476ce5c3f0edc31c5e777adf082b56541e25aaf43aafaa | O=C1O[C@@H](Cn2ccnn2)CN1c1ccccc1 | [#8:1]-[C:2]-[C:3]-[N;H0;D2;+0:4]=[N+;H0;D2:5]=[N-;H0;D1:6].[CH;D1;+0:7]#[C;H0;D2;+0:8]-[C:9]-[O;D1;H1:10]>>[#8:1]-[C:2]-[C:3]-[n;H0;D3;+0:4]1:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[C:9]-[O;D1;H1:10]):[n;H0;D2;+0:6]:[n;H0;D2;+0:5]:1 | 105.1 | [{"value": 105.1, "product": "FC=1C=C(C=CC1I)N1C(O[C@H](C1)CN1N=NC(=C1)CO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (5R)-3-(3-Fluoro-4-iodophenyl)-5-(azidomethyl)oxazolidin-2-one (10 g, 28 mmol) was dissolved in acetonitrile (80 mL). Propargyl alcohol (3.2 mL, 56 mmol) was added and then CuI (526 mg, 2.8 mmol) and it was stirred overnight. The solidified reaction mixture was extracted with ethyl acetate/acetonitrile, washed with wat... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Alkyne | null | null | c1c[nH]nn1 | C1COC[NH]1.c1c[nH]nn1.c1ccccc1 | null | [Cu]I.C(C)#N | null | null | C#CCO.[N-]=[N+]=NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1>[Cu]I.C(C)#N>O=C1O[C@@H](Cn2cc(CO)nn2)CN1c1ccc(I)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-47e842f87cde4cdebc9744f952354621 | CC1(C)OB(c2ccc(N3C[C@H](Cn4ccnn4)OC3=O)cc2F)OC1(C)C.Cc1cn(-c2ccc(Br)c(C)n2)nn1>>Cc1cn(-c2ccc(-c3ccc(N4C[C@H](Cn5ccnn5)OC4=O)cc3F)c(C)n2)nn1 | BrC=1C(=NC(=CC1)N1N=NC(=C1)C)C.C([O-])([O-])=O.[K+].[K+].FC=1C=C(C=CC1B1OC(C(O1)(C)C)(C)C)N1C(O[C@H](C1)CN1N=NC=C1)=O>>FC=1C=C(C=CC1C=1C(=NC(=CC1)N1N=NC(=C1)C)C)N1C(O[C@H](C1)CN1N=NC=C1)=O | CC1(C)OB([c:9]2[cH:10][cH:11][c:12]([N:13]3[CH2:14][C@H:15]([CH2:16][n:17]4[cH:18][cH:19][n:20][n:21]4)[O:22][C:23]3=[O:24])[cH:25][c:26]2[F:27])OC1(C)C.Br[c:8]1[cH:7][cH:6][c:5](-[n:4]2[cH:3][c:2]([CH3:1])[n:32][n:31]2)[n:30][c:28]1[CH3:29]>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]... | CC1(C)OB(c2ccc(N3C[C@H](Cn4ccnn4)OC3=O)cc2F)OC1(C)C.Cc1cn(-c2ccc(Br)c(C)n2)nn1 | Cc1cn(-c2ccc(-c3ccc(N4C[C@H](Cn5ccnn5)OC4=O)cc3F)c(C)n2)nn1 | null | C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)[Pd-4](P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | O.CN(C)C=O | C-C Coupling | Suzuki coupling with boronic esters | 41faa5d7c8b2fa5e7977311a48e89454061b096772c8348f0e02516e76bb87f9 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | O=C1O[C@@H](Cn2ccnn2)CN1c1ccc(-c2ccc(-n3ccnn3)nc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[C;D1;H3:7].C-C1(-C)-O-B(-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[F;D1;H0:12]):[c:13])-O-C-1(-C)-C>>[C;D1;H3:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[F;D1;H0:12]):[c:13] | null | [] | 80 | CELSIUS | null | null | 3-Bromo-2-methyl-6-(4-methyl-1H-1,2,3-triazol-1-yl)pyridine (196 mg, 0.773 mmol), (5R)-3-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (300 mg, 0.773 mmol), potassium carbonate (320 mg, 2.31 mmol), and tetrakis(triphenylphosphino) palladium(0) (89 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | B1OCCO1.c1ccccc1.c1ccncc1 | c1ccncc1.c1ccccc1 | c1c[nH]nn1.c1ccncc1.c1ccccc1.C1COC[NH]1.c1c[nH]nn1 | HBr.B | C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)[Pd-4](P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O.CN(C)C=O | 80 | null | CC1(C)OB(c2ccc(N3C[C@H](Cn4ccnn4)OC3=O)cc2F)OC1(C)C.Cc1cn(-c2ccc(Br)c(C)n2)nn1>C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)[Pd-4](P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.O.CN(C)C=O>Cc1cn(-c2ccc(-c3ccc(N4C[C@H](Cn5ccnn5)OC4=O)cc3F)c(C)n2)nn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-42d0ee93fb3c470fbb2c1cd518101bc1 | CCOC(=O)c1cncn1-c1ccc(Br)cc1>>O=Cc1cncn1-c1ccc(Br)cc1 | BrC1=CC=C(C=C1)N1C=NC=C1C(=O)OCC.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>BrC1=CC=C(C=C1)N1C=NC=C1C=O | CCO[C:2](=[O:1])[c:3]1[cH:4][n:5][cH:6][n:7]1-[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1>>[O:1]=[CH:2][c:3]1[cH:4][n:5][cH:6][n:7]1-[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1 | CCOC(=O)c1cncn1-c1ccc(Br)cc1 | O=Cc1cncn1-c1ccc(Br)cc1 | null | O=[Mn]=O | null | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | c1ccc(-n2ccnc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1-[c:8]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1-[c:8] | null | [] | null | null | null | null | Ethyl 1-(4-bromophenyl)-1H-imidazole-5-carboxylate (4) was constructed through the condensation of tosylmethyl isocyanide and hemi-aminal 3, which in turn was produced by the addition of 4-bromoaniline (2) to ethyl glyoxalate (1). Ester 4 was reduced with LiAlH4 at −40° C. and the resulting alcohol 5 oxidised with MnO2... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1c[nH]cn1.c1ccccc1 | HO- | O=[Mn]=O | null | null | CCOC(=O)c1cncn1-c1ccc(Br)cc1>O=[Mn]=O>O=Cc1cncn1-c1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-656fa2eeb7774f56b51c184b681db2d5 | CCOC(=O)C=O.Nc1ccc(Br)cc1.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1>>CCOC(=O)c1cncn1-c1ccc(Br)cc1 | S(=O)(=O)(C1=CC=C(C)C=C1)C[N+]#[C-].C([O-])([O-])=O.[K+].[K+].BrC1=CC=C(N)C=C1.C(C=O)(=O)OCC>>BrC1=CC=C(C=C1)N1C=NC=C1C(=O)OCC | O=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:10][c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1.Cc1ccc(S(=O)(=O)[CH2:7][N+:8]#[C-:9])cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][cH:9][n:10]1-[c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1 | CCOC(=O)C=O.Nc1ccc(Br)cc1.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1 | CCOC(=O)c1cncn1-c1ccc(Br)cc1 | null | null | O.CO | Functional Group Interconversion | OtherReaction | 790141dec70a8890d75a9279055d6de4d058fd396547d17fc6ff360602f4570d | 6dc0e887e4960e0f4d9a5a0cba684dc6d746b402ae31b1252885ca90017f6cab | c1ccc(-n2ccnc2)cc1 | C-c1:c:c:c(-S(=O)(=O)-[CH2;D2;+0:1]-[N+;H0;D2:2]#[C-;H0;D1:3]):c:c:1.O=[CH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8].[NH2;D1;+0:9]-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:4]1:[cH;D2;+0:1]:[n;H0;D2;+0:2]:[cH;D2;+0:3]:[n;H0;D3;+0:9]:1-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:... | null | [] | 65 | CELSIUS | null | null | To a solution of 4-bromoaniline (8.6 g, 50 mmol) in MeOH (100 mL) was added ethyl glyoxalate (12 mL, 60 mmol, 50% in toluene) and the resulting mixture heated at reflux for 3.5 h. The mixture was then concentrated in vacuo and the resulting residue reconstituted in anhydrous ethanol (100 mL) and treated with tosylmethy... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aldehyde.Ester.Isocyanide.Primary amine | Ester | c1ccccc1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1 | TsOH.HO- | O.CO | 65 | null | CCOC(=O)C=O.Nc1ccc(Br)cc1.[C-]#[N+]CS(=O)(=O)c1ccc(C)cc1>O.CO>CCOC(=O)c1cncn1-c1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b03797087294a0d99f2e58bd6eedff2 | CCOC(=O)c1cncn1-c1ccc(Br)cc1>>OCc1cncn1-c1ccc(Br)cc1 | BrC1=CC=C(C=C1)N1C=NC=C1C(=O)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>BrC1=CC=C(C=C1)N1C=NC=C1CO | CCO[C:2](=[O:1])[c:3]1[cH:4][n:5][cH:6][n:7]1-[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1>>[OH:1][CH2:2][c:3]1[cH:4][n:5][cH:6][n:7]1-[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1 | CCOC(=O)c1cncn1-c1ccc(Br)cc1 | OCc1cncn1-c1ccc(Br)cc1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-n2ccnc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1-[c:8]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1-[c:8] | null | [] | -20 | CELSIUS | null | null | To a solution of 3-(4-bromophenyl)-3H-imidazole-4-carboxylic acid ethyl ester (4) (590 mg, 2.0 mmol) in dry THF was added lithium aluminium hydride (2.4 mL, 2.4 mmol, 1.0M in THF) dropwise at −40° C. under nitrogen, and the resulting mixture slowly warmed to −20° C. over 1 h. The reaction mixture was then quenched with... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1c[nH]cn1.c1ccccc1 | HO- | C1CCOC1 | -20 | null | CCOC(=O)c1cncn1-c1ccc(Br)cc1>C1CCOC1>OCc1cncn1-c1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b1788e5ee98e4e9cbc69387c0824d955 | OCc1cncn1-c1ccc(Br)cc1>>O=Cc1cncn1-c1ccc(Br)cc1 | BrC1=CC=C(C=C1)N1C=NC=C1CO>>BrC1=CC=C(C=C1)N1C=NC=C1C=O | [OH:1][CH2:2][c:3]1[cH:4][n:5][cH:6][n:7]1-[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1>>[O:1]=[CH:2][c:3]1[cH:4][n:5][cH:6][n:7]1-[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1 | OCc1cncn1-c1ccc(Br)cc1 | O=Cc1cncn1-c1ccc(Br)cc1 | null | O=[Mn]=O | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(-n2ccnc2)cc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1-[c:8]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:1-[c:8] | null | [] | null | null | 8 | HOUR | To a solution of [3-(4-bromophenyl)-3H-imidazol-4-yl]-methanol (5) (500 mg, 2.0 mmol) in dry methylene chloride (30 mL) was added MnO2 (1.74 g, 20.0 mmol) and the resulting mixture stirred overnight at rt. The suspension was then filtered through Celite and the filtrate concentrated under reduced pressure to give 3-(4-... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1c[nH]cn1.c1ccccc1 | null | O=[Mn]=O.C(Cl)Cl | null | 8 | OCc1cncn1-c1ccc(Br)cc1>O=[Mn]=O.C(Cl)Cl>O=Cc1cncn1-c1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d3d304294c004309891cd15c622547b4 | CCOC(=O)CN=[N+]=[N-].O=Cc1cncn1-c1ccc(Br)cc1>>CCOC(=O)C(=Cc1cncn1-c1ccc(Br)cc1)N=[N+]=[N-] | [O-]CC.[K+].C(Cl)Cl.N(=[N+]=[N-])CC(=O)OCC.BrC1=CC=C(C=C1)N1C=NC=C1C=O>>N(=[N+]=[N-])C(C(=O)OCC)=CC=1N(C=NC1)C1=CC=C(C=C1)Br | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:20]=[N+:21]=[N-:22].O=[CH:7][c:8]1[cH:9][n:10][cH:11][n:12]1-[c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][c:8]1[cH:9][n:10][cH:11][n:12]1-[c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]1)[N:20]=[N+:21]=[N-:22] | CCOC(=O)CN=[N+]=[N-].O=Cc1cncn1-c1ccc(Br)cc1 | CCOC(=O)C(=Cc1cncn1-c1ccc(Br)cc1)N=[N+]=[N-] | null | null | CCO.C(C)O | C-C Coupling | Aldol condensation | a86984aeb4a9963534e0b081b0ecca18455fda1775f36ce168d1ca4cf966df3e | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccc(-n2ccnc2)cc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1-[c:7].[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[CH2;D2;+0:12]-[#7:13]=[#7;+:14]=[N;-;D1;H0:15]>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C;H0;D3;+0:12](-[#7:13]=[#7;+:14]=[N;-;D1;H0:15])=[CH;D2;+0:1]-[c:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1-[c:7] | null | [] | 0 | CELSIUS | 5 | HOUR | A commercially available 34% methylene chloride solution of ethyl azidoacetate (6.6 mL, 21.6 mmol) was concentrated in vacuo, the residue reconstituted in anhydrous ethanol (100 mL) and the resulting solution treated with 3-(4-bromophenyl)-3H-imidazole-4-carbaldehyde (6) (2.7 g, 10.8 mmol). The mixture was cooled to 0°... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | null | null | c1c[nH]cn1.c1ccccc1 | HO- | CCO.C(C)O | 0 | 5 | CCOC(=O)CN=[N+]=[N-].O=Cc1cncn1-c1ccc(Br)cc1>CCO.C(C)O>CCOC(=O)C(=Cc1cncn1-c1ccc(Br)cc1)N=[N+]=[N-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ace680e17e364703b31d189b7e87f60f | CCOC(=O)C(=Cc1cncn1-c1ccc(Br)cc1)N=[N+]=[N-]>>CCOC(=O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1 | N(=[N+]=[N-])C(C(=O)OCC)=CC=1N(C=NC1)C1=CC=C(C=C1)Br>>BrC1=CC=C(C=C1)N1C=NC2=C1C=C(N2)C(=O)OCC | [N-]=[N+]=[N:20][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:7][c:8]1[cH:9][n:10][cH:11][n:12]1-[c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([n:10][cH:11][n:12]2-[c:13]2[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]2)[nH:20]1 | CCOC(=O)C(=Cc1cncn1-c1ccc(Br)cc1)N=[N+]=[N-] | CCOC(=O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1 | null | null | CC=1C=CC(=CC1)C | Aromatic Heterocycle Formation | OtherReaction | 32d9ab007c9f73c24e4f800934abe1afd5a0f34e40aa15798048223246b54b0a | 92e44103d9eed82e18506de89438be8bcf71f9d4943ea64c754ba56033058a29 | c1ccc(-n2cnc3[nH]ccc32)cc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](=[CH;D2;+0:6]-[c:7]1:[cH;D2;+0:8]:[#7;a:9]:[c:10]:[#7;a:11]:1-[c:12])-[N;H0;D2;+0:13]=[N+]=[N-]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]2:[#7;a:11](-[c:12]):[c:10]:[#7;a:9]:[c;H0;D3;+0:8]:2:[nH;D2;+0:13]:1 | null | [] | null | null | null | null | A suspension of ethyl 2-azido-3-[3-(4-bromophenyl)-3H-imidazol-4-yl]acrylate (7) (240 mg) in p-xylene (10 mL) was heated at reflux under nitrogen for 30 min. The mixture was then cooled to rt, and the resulting white solid was collected by filtration, washed with hexane, and dried in air to yield ethyl 1-(4-bromophenyl... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Azide | Ester | c1c[nH]cn1 | c1cc2ncnc2n1 | c1cc2ncnc2n1.c1ccccc1 | Other | CC=1C=CC(=CC1)C | null | null | CCOC(=O)C(=Cc1cncn1-c1ccc(Br)cc1)N=[N+]=[N-]>CC=1C=CC(=CC1)C>CCOC(=O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4cc9605e04d242ada0ec88c62eaef81a | CCOC(=O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1>>CCOC(=O)c1cc2c(ncn2-c2ccccc2)[nH]1 | BrC1=CC=C(C=C1)N1C=NC2=C1C=C(N2)C(=O)OCC>>C1(=CC=CC=C1)N1C=NC2=C1C=C(N2)C(=O)OCC | Br[c:16]1[cH:15][cH:14][c:13](-[n:12]2[c:8]3[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[nH:19][c:9]3[n:10][cH:11]2)[cH:18][cH:17]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([n:10][cH:11][n:12]2-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[nH:19]1 | CCOC(=O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1 | CCOC(=O)c1cc2c(ncn2-c2ccccc2)[nH]1 | null | [Pd] | C(C)(=O)OCC.C(C)O | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccc(-n2cnc3[nH]ccc32)cc1 | Br-[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 | 16 | HOUR | A suspension of ethyl 1-(4-bromophenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate (EXAMPLE 1) (50 mg) and 10% Pd—C (100 mg) in ethanol (10 mL) and ethyl acetate (10 mL), was hydrogenated at atmospheric pressure for 16 h. The catalyst was removed by filtration through Celite and the filtrate concentrated in vacuo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1cc2ncnc2n1.c1ccccc1 | Br- | [Pd].C(C)(=O)OCC.C(C)O | null | 16 | CCOC(=O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1>[Pd].C(C)(=O)OCC.C(C)O>CCOC(=O)c1cc2c(ncn2-c2ccccc2)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74121647bdbe46a59ddd8d49912b0259 | CCOC(=O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1>>O=C(O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1 | BrC1=CC=C(C=C1)N1C=NC2=C1C=C(N2)C(=O)OCC.[OH-].[Na+].Cl>>BrC1=CC=C(C=C1)N1C=NC2=C1C=C(N2)C(=O)O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][c:6]2[c:7]([n:8][cH:9][n:10]2-[c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]2)[nH:18]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]2[c:7]([n:8][cH:9][n:10]2-[c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]2)[nH:18]1 | CCOC(=O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1 | O=C(O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-n2cnc3[nH]ccc32)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | null | null | To a suspension of ethyl 1-(4-bromophenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate (EXAMPLE 1) (95 mg) in ethanol (3 mL) was added 1 mL of 3N NaOH and the mixture heated at reflux for 6 h, after which time mixture was cooled to rt and acidified with 3N HCl to pH=3. The resulting off-white solid was collected b... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc2ncnc2n1.c1ccccc1 | Other | C(C)O | null | null | CCOC(=O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1>C(C)O>O=C(O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-125b9fe47c234e919dab90e1084a743f | COCCN.O=C(O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1>>COCCNC(=O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1 | COCCN.BrC1=CC=C(C=C1)N1C=NC2=C1C=C(N2)C(=O)O.C1=CN(C=N1)C(=O)N2C=CN=C2.CCN(C(C)C)C(C)C>>BrC1=CC=C(C=C1)N1C=NC2=C1C=C(N2)C(=O)NCCOC | [CH3:1][O:2][CH2:3][CH2:4][NH2:5].O[C:6](=[O:7])[c:8]1[cH:9][c:10]2[c:11]([n:12][cH:13][n:14]2-[c:15]2[cH:16][cH:17][c:18]([Br:19])[cH:20][cH:21]2)[nH:22]1>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[c:8]1[cH:9][c:10]2[c:11]([n:12][cH:13][n:14]2-[c:15]2[cH:16][cH:17][c:18]([Br:19])[cH:20][cH:21]2)[nH:22]1 | COCCN.O=C(O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1 | COCCNC(=O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1 | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(-n2cnc3[nH]ccc32)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5](:[#7;a:6]):[c:7](:[#7;a:8]):[c:9]:1.[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;a:6]:[c:5]1:[#7;a:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:12]-[C:11]-[C:10]):[c:9]:[c:7]:1:[#7;a:8] | null | [] | 60 | CELSIUS | 1 | HOUR | A mixture of 1-(4-bromophenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylic acid (70 mg, 0.23 mmol), CDI (75 mg, 0.46 mmol) and DIPEA (0.1 mL) in dry THF (3 mL) was stirred at 60° C. for 1 h and then treated with 2-methoxyethylamine (0.1 mL). After additional 2 h at 60° C., the mixture was concentrated under reduced... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cc2ncnc2n1.c1ccccc1 | HO- | C1CCOC1 | 60 | 1 | COCCN.O=C(O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1>C1CCOC1>COCCNC(=O)c1cc2c(ncn2-c2ccc(Br)cc2)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-635c09f7414c468697d9ae4969cf7673 | CCOC(=O)c1cc2c(ncn2-c2cccc(Br)c2)[nH]1.OB(O)c1ccsc1>>CCOC(=O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 | BrC=1C=C(C=CC1)N1C=NC2=C1C=C(N2)C(=O)OCC.BrC=1C=C(N)C=CC1.S1C=C(C=C1)B(O)O>>S1C=C(C=C1)C=1C=C(C=CC1)N1C=NC2=C1C=C(N2)C(=O)OCC | Br[c:17]1[cH:16][cH:15][cH:14][c:13](-[n:12]2[c:8]3[cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[nH:24][c:9]3[n:10][cH:11]2)[cH:23]1.OB(O)[c:18]1[cH:19][cH:20][s:21][cH:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]2[c:9]([n:10][cH:11][n:12]2-[c:13]2[cH:14][cH:15][cH:16][c:17](-[c:18]3[cH:19][cH:20][s:21][cH:2... | CCOC(=O)c1cc2c(ncn2-c2cccc(Br)c2)[nH]1.OB(O)c1ccsc1 | CCOC(=O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 | 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 | null | C-C Coupling | Suzuki coupling with boronic acids | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cc(-c2ccsc2)cc(-n2cnc3[nH]ccc32)c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[#16;a:9]:[c:10]:1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[#16;a:9]:[c:10]:1):[c:2]:[c:3] | 97.5 | [{"value": 97.5, "product": "S1C=C(C=C1)C=1C=C(C=CC1)N1C=NC2=C1C=C(N2)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | A flask containing a mixture of ethyl 1-(3-bromophenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate (334 mg, 1 mmol, prepared according to the procedure described for example 1 except using 3-bromoaniline in the first step) and 3-thiophene boronic acid (256 mg, 2 mmol) was degassed and placed under a nitrogen atmo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1cc2ncnc2n1.c1ccccc1.c1ccsc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | 85 | null | CCOC(=O)c1cc2c(ncn2-c2cccc(Br)c2)[nH]1.OB(O)c1ccsc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>CCOC(=O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1db183c7ce8e43e3853e245c13d60224 | CCOC(=O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1>>OCc1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 | S1C=C(C=C1)C=1C=C(C=CC1)N1C=NC2=C1C=C(N2)C(=O)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>S1C=C(C=C1)C=1C=C(C=CC1)N1C=NC2=C1C=C(N2)CO | CCO[C:2](=[O:1])[c:3]1[cH:4][c:5]2[c:6]([n:7][cH:8][n:9]2-[c:10]2[cH:11][cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][s:18][cH:19]3)[cH:20]2)[nH:21]1>>[OH:1][CH2:2][c:3]1[cH:4][c:5]2[c:6]([n:7][cH:8][n:9]2-[c:10]2[cH:11][cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][s:18][cH:19]3)[cH:20]2)[nH:21]1 | CCOC(=O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 | OCc1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1cc(-c2ccsc2)cc(-n2cnc3[nH]ccc32)c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[#7;a:4]:[c:5](:[#7;a:6]):[c:7](:[#7;a:8]):[c:9]:1>>[#7;a:6]:[c:5]1:[#7;a:4]:[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:9]:[c:7]:1:[#7;a:8] | 15.5 | [{"value": 15.5, "product": "S1C=C(C=C1)C=1C=C(C=CC1)N1C=NC2=C1C=C(N2)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.4, "product": "S1C=C(C=C1)C=1C=C(C=CC1)N1C=NC2=C1C=C(N2)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | null | null | To a solution of ethyl 1-(3-thien-3-ylphenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate (300 mg, 0.89 mmol) in dry THF (9 mL) was added lithium aluminum hydride (1.07 mL, 1.07 mmol, 1.0 M in THF) dropwise at −40° C. under nitrogen. The resulting solution was allowed to slowly warm to −20° C. over the course of 1... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cc2ncnc2n1.c1ccccc1.c1ccsc1 | HO- | C1CCOC1 | -20 | null | CCOC(=O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1>C1CCOC1>OCc1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-28461a2369bb4d2cbe3b1308af601c93 | CCOC(=O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1>>O=C(O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 | S1C=C(C=C1)C=1C=C(C=CC1)N1C=NC2=C1C=C(N2)C(=O)OCC.[OH-].[Na+].Cl>>S1C=C(C=C1)C=1C=C(C=CC1)N1C=NC2=C1C=C(N2)C(=O)O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][c:6]2[c:7]([n:8][cH:9][n:10]2-[c:11]2[cH:12][cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][s:19][cH:20]3)[cH:21]2)[nH:22]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]2[c:7]([n:8][cH:9][n:10]2-[c:11]2[cH:12][cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][s:19][cH:20]3)[cH:21]2)[nH:22]1 | CCOC(=O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 | O=C(O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 | null | null | C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cc(-c2ccsc2)cc(-n2cnc3[nH]ccc32)c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 68 | [{"value": 68.0, "product": "S1C=C(C=C1)C=1C=C(C=CC1)N1C=NC2=C1C=C(N2)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of ethyl 1-(3-thien-3-ylphenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate (500 mg, 1.5 mmol, prepared as described in the procedure for example 5) in THF (10 mL) was added aqueous sodium hydroxide (416 mg in 4 mL H2O, 10.4 mmol) and the mixture heated at reflux for 16 hr. After this time, t... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc2ncnc2n1.c1ccccc1.c1ccsc1 | Other | C1CCOC1 | null | null | CCOC(=O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1>C1CCOC1>O=C(O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-38445b03d25147f2bd695e5e6f7d387a | CN.O=C(O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1>>CNC(=O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 | O.S1C=C(C=C1)C=1C=C(C=CC1)N1C=NC2=C1C=C(N2)C(=O)O.C(CCl)Cl.CN>>CNC(=O)C1=CC2=C(N=CN2C2=CC(=CC=C2)C2=CSC=C2)N1 | [CH3:1][NH2:2].O[C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([n:9][cH:10][n:11]2-[c:12]2[cH:13][cH:14][cH:15][c:16](-[c:17]3[cH:18][cH:19][s:20][cH:21]3)[cH:22]2)[nH:23]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([n:9][cH:10][n:11]2-[c:12]2[cH:13][cH:14][cH:15][c:16](-[c:17]3[cH:18][cH:19][s:20][cH:21]3)[cH:22]2)[nH:2... | CN.O=C(O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 | CNC(=O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 | null | CN(C)C=1C=CN=CC1 | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1cc(-c2ccsc2)cc(-n2cnc3[nH]ccc32)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5](:[#7;a:6]):[c:7](:[#7;a:8]):[c:9]:1.[C;D1;H3:10]-[NH2;D1;+0:11]>>[#7;a:8]:[c:7]1:[c:9]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C;D1;H3:10]):[#7;a:4]:[c:5]:1:[#7;a:6] | 4.3 | [{"value": 4.3, "product": "CNC(=O)C1=CC2=C(N=CN2C2=CC(=CC=C2)C2=CSC=C2)N1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 4.2, "product": "CNC(=O)C1=CC2=C(N=CN2C2=CC(=CC=C2)C2=CSC=C2)N1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 1-(3-thien-3-ylphenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylic acid (60 mg, 0.2 mmol), EDC (44.6 mg, 0.97 mmol) and DMAP (7.1 mg, 0.06 mmol) in dry DMF (1.5 mL) was stirred at room temperature under nitrogen for 30 minutes. Methylamine (0.5 mL, 0.97 mmol, 2M solution in THF) was then added and the... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cc2ncnc2n1.c1ccccc1.c1ccsc1 | HO- | CN(C)C=1C=CN=CC1.CN(C)C=O | null | 8 | CN.O=C(O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1>CN(C)C=1C=CN=CC1.CN(C)C=O>CNC(=O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0b538ffc8bcd4c3f95e5a5c7483d1a82 | O=C(O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1>>COC(=O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 | S1C=C(C=C1)C=1C=C(C=CC1)N1C=NC2=C1C=C(N2)C(=O)O.C([O-])(O)=O.[Na+]>>S1C=C(C=C1)C=1C=C(C=CC1)N1C=NC2=C1C=C(N2)C(=O)OC | [OH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([n:9][cH:10][n:11]2-[c:12]2[cH:13][cH:14][cH:15][c:16](-[c:17]3[cH:18][cH:19][s:20][cH:21]3)[cH:22]2)[nH:23]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[c:8]([n:9][cH:10][n:11]2-[c:12]2[cH:13][cH:14][cH:15][c:16](-[c:17]3[cH:18][cH:19][s:20][cH:21]3)[cH:22]2)[nH:23]1 | O=C(O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 | COC(=O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 | null | S(O)(O)(=O)=O | CO | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | c1cc(-c2ccsc2)cc(-n2cnc3[nH]ccc32)c1 | [#7;a:1]:[c:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[#7;a:1]:[c:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[C;D1;H3:6] | 30.3 | [{"value": 30.3, "product": "S1C=C(C=C1)C=1C=C(C=CC1)N1C=NC2=C1C=C(N2)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of 1-(3-thien-3-ylphenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylic acid (200 mg, 0.65 mmol, prepared as described in the procedure for example 6) in methanol (10 mL) was added concentrated sulfuric acid (5 drops). The solution was heated at reflux for 36 h then cooled to room temperature, b... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1cc2ncnc2n1.c1ccccc1.c1ccsc1 | Other | S(O)(O)(=O)=O.CO | null | null | O=C(O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1>S(O)(O)(=O)=O.CO>COC(=O)c1cc2c(ncn2-c2cccc(-c3ccsc3)c2)[nH]1 |
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