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-03ba810b7f464a06b5d8787af2e8b64e | ord-3a460190a33246fe89fcd72452a31c42 | CC(C)C1CCC(=O)C(Br)C1.N#CC1(c2ccccc2)CCC(=O)CC1>>N#CC1(c2ccccc2)CCC(=O)C(Br)C1 | O=C1CCC(CC1)(C#N)C1=CC=CC=C1.BrC1C(CCC(C1)C(C)C)=O>>BrC1CC(CCC1=O)(C#N)C1=CC=CC=C1 | CC(C)C1C[CH2:11][C:12](=[O:13])[CH:14]([Br:15])[CH2:16]1.O=C1CC[C:3]([C:2]#[N:1])([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[CH2:10]C1>>[N:1]#[C:2][C:3]1([c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[CH2:10][CH2:11][C:12](=[O:13])[CH:14]([Br:15])[CH2:16]1 | CC(C)C1CCC(=O)C(Br)C1.N#CC1(c2ccccc2)CCC(=O)CC1 | N#CC1(c2ccccc2)CCC(=O)C(Br)C1 | null | null | null | C-C Coupling | Bromination | 63a5bbb7584869c734c57121d2a924fb323d55cf29a98933c11896490672bc05 | 6724ccabc3992a670343bf52a7363504b61386c3d76e13c5adf76934d5aec2b7 | O=C1CCC(c2ccccc2)CC1 | C-C(-C)-C1-C-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4](-[Br;D1;H0:5])-[CH2;D2;+0:6]-1.O=C1-C-C-[C;H0;D4;+0:7](-[C:8]#[N;D1;H0:9])(-[c:10](:[c:11]):[c:12])-[CH2;D2;+0:13]-C-1>>[Br;D1;H0:5]-[C:4]1-[CH2;D2;+0:6]-[C;H0;D4;+0:7](-[C:8]#[N;D1;H0:9])(-[c:10](:[c:11]):[c:12])-[CH2;D2;+0:13]-[CH2;D2;+0:1]-[C:2]-1=[O;D1;H0:3] | null | [] | null | null | null | null | The bromination of 4-oxo-1-phenyl-cyclohexanecarbonitrile takes place in a manner similar to that described above for the preparation of 2-bromo-4-isopropyl-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | c1ccccc1.C1CCCCC1 | HO- | null | null | null | CC(C)C1CCC(=O)C(Br)C1.N#CC1(c2ccccc2)CCC(=O)CC1>>N#CC1(c2ccccc2)CCC(=O)C(Br)C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-777ab7736df042afb2a421bd409f5134 | COCCOC.OB(O)Oc1ccc(F)cc1>>Fc1ccc(C2=CCC3(CC2)OCCO3)cc1 | COCCOC.C([O-])([O-])=O.[Na+].[Na+].FC1=CC=C(C=C1)OB(O)O.[Cl-].[Li+]>>FC1=CC=C(C=C1)C1=CCC2(OCCO2)CC1 | [CH3:7][O:15][CH2:14][CH2:13][O:12][CH3:8].OB(O)O[c:5]1[cH:4][cH:3][c:2]([F:1])[cH:17][cH:16]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][CH2:8][C:9]3([CH2:10][CH2:11]2)[O:12][CH2:13][CH2:14][O:15]3)[cH:16][cH:17]1 | COCCOC.OB(O)Oc1ccc(F)cc1 | Fc1ccc(C2=CCC3(CC2)OCCO3)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 73d3390cdfc82df940a9bfe109a2c7ae6eaff0c43ec12d38d34a324e77866b6b | 1a58d07059c3da57a6f490c1b3709f375685d946bef37dda9f78ddb82ba38d2b | C1=C(c2ccccc2)CCC2(C1)OCCO2 | O-B(-O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH3;D1;+0:6]-[O;H0;D2;+0:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-[CH3;D1;+0:11]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[C:12]1=[CH;D2;+0:6]-[CH2;D2;+0:11]-[C:13]2(-[C:14]-[C:15]-1)-[O;H0;D2;+0:10]-[C:9]-[C:8]-[O;H0;D2;+0:7]-2):[c:4]:[c:5] | null | [] | 80 | CELSIUS | 8 | HOUR | In an argon-charged flask, 2M sodium carbonate (4.8 mmol), 1,2-dimethoxyethane (8 ml), 4-fluorophenylboric acid (2.8 mmol), lithium chloride (6 mmol), 1,4-dioxaspiro[4.5]dec-7-en-8-yl-trifluormethane-sulphonic acid ester (2 mmol) and tetrakis(triphenyl-phosphine)palladium (0.1 mmol) are combined and stirred overnight a... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ether.Ether | c1ccccc1 | c1ccccc1.C1=CCC2(CC1)OCCO2 | c1ccccc1.C1=CCC2(CC1)OCCO2 | null | null | 80 | 8 | COCCOC.OB(O)Oc1ccc(F)cc1>>Fc1ccc(C2=CCC3(CC2)OCCO3)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d3ec7ce35c5743429efed8cc6b073b42 | Fc1ccc(C2=CCC3(CC2)OCCO3)cc1>>Fc1ccc(C2CCC3(CC2)OCCO3)cc1 | FC1=CC=C(C=C1)C1=CCC2(OCCO2)CC1.[H][H]>>FC1=CC=C(C=C1)C1CCC2(OCCO2)CC1 | [F:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[CH:7][CH2:8][C:9]3([CH2:10][CH2:11]2)[O:12][CH2:13][CH2:14][O:15]3)[cH:16][cH:17]1>>[F:1][c:2]1[cH:3][cH:4][c:5]([CH:6]2[CH2:7][CH2:8][C:9]3([CH2:10][CH2:11]2)[O:12][CH2:13][CH2:14][O:15]3)[cH:16][cH:17]1 | Fc1ccc(C2=CCC3(CC2)OCCO3)cc1 | Fc1ccc(C2CCC3(CC2)OCCO3)cc1 | null | [Pd] | null | Reduction | Hydrogenation (double to single) | 0d0e26d2718cccdfb38e87235a0691a84f376bed6c3bb4800c59f1ea8662f0be | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(C2CCC3(CC2)OCCO3)cc1 | [#8:1]-[C:2]1(-[#8:3])-[C:4]-[C:5]-[C;H0;D3;+0:6](-[c:7](:[c:8]):[c:9])=[CH;D2;+0:10]-[C:11]-1>>[#8:1]-[C:2]1(-[#8:3])-[C:4]-[C:5]-[CH;D3;+0:6](-[c:7](:[c:8]):[c:9])-[CH2;D2;+0:10]-[C:11]-1 | null | [] | null | null | null | null | 8-(4-fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene is hydrogenated using Pd/C with hydrogen. After filtering-off of the catalyst over celite and evaporating-off of the solvent, 8-(4-fluorophenyl)-1,4-dioxaspiro[4.5]decane is obtained in a quantitative yield: tR 3.65 min (LC-1); ESI-MS(+): m/z 237.26 [M+H]+.
Conditions: Se... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CCC2(CC1)OCCO2 | C1CCC2(CC1)OCCO2 | c1ccccc1.C1CCC2(CC1)OCCO2 | null | [Pd] | null | null | Fc1ccc(C2=CCC3(CC2)OCCO3)cc1>[Pd]>Fc1ccc(C2CCC3(CC2)OCCO3)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-078b576691f14997974b7557469bacb0 | Fc1ccc(C2CCC3(CC2)OCCO3)cc1>>O=C1CCC(c2ccc(F)cc2)CC1 | FC1=CC=C(C=C1)C1CCC2(OCCO2)CC1.S(O)(O)(=O)=O>>FC1=CC=C(C=C1)C1CCC(CC1)=O | C1C[O:1][C:2]2(O1)[CH2:3][CH2:4][CH:5]([c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]1)[CH2:13][CH2:14]2>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([c:6]2[cH:7][cH:8][c:9]([F:10])[cH:11][cH:12]2)[CH2:13][CH2:14]1 | Fc1ccc(C2CCC3(CC2)OCCO3)cc1 | O=C1CCC(c2ccc(F)cc2)CC1 | null | null | O1CCOCC1 | Miscellaneous | Ketal hydrolysis to ketone | 7165849453c1f3f22c37497ec202aa2a6a319b018b3ae9fffa16fa9182ebd128 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1CCC(c2ccccc2)CC1 | [C:1]-[C:2]-[C;H0;D4;+0:3]1(-O-C-C-[O;H0;D2;+0:4]-1)-[C:5]-[C:6]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6] | null | [] | null | null | 5 | HOUR | 8-(4-fluor-phenyl)-1,4-dioxaspiro[4.5]decane (2 mmol) is dissolved in dioxane (6.5 ml) and treated with 3 ml 50% aqueous sulphuric acid accompanied by stirring at room temperature for 5 hours. After dilution with water (12 ml) extraction is carried out twice with dichloromethane. The raw title compound is obtained from... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1CCC2(CC1)OCCO2 | C1CCCCC1 | C1CCCCC1.c1ccccc1 | HO- | O1CCOCC1 | null | 5 | Fc1ccc(C2CCC3(CC2)OCCO3)cc1>O1CCOCC1>O=C1CCC(c2ccc(F)cc2)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4e04740b06094fcd8dc0daa397a469a5 | CC(C)C1CCC(=O)C(Br)C1.CC1(C)CC(=O)CCC1c1ccccc1>>CC1(C)CC(=O)C(Br)CC1c1ccccc1 | CC1(CC(CCC1C1=CC=CC=C1)=O)C.BrC1C(CCC(C1)C(C)C)=O>>BrC1C(CC(C(C1)C1=CC=CC=C1)(C)C)=O | CC(C)C1CCC(=O)C([Br:8])C1.[CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[O:6])[CH2:7][CH2:9][CH:10]1[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[O:6])[CH:7]([Br:8])[CH2:9][CH:10]1[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | CC(C)C1CCC(=O)C(Br)C1.CC1(C)CC(=O)CCC1c1ccccc1 | CC1(C)CC(=O)C(Br)CC1c1ccccc1 | null | null | null | Functional Group Interconversion | Bromination | a46c7dc769608b8ec35dadd804e0f7a74a028f2146ee0122a9c24d2aaae96684 | af6f895a0e88516f0a2e7e54838a1e72c142a95d71091e6b02ff568a7310f7ea | O=C1CCC(c2ccccc2)CC1 | C-C(-C)-C1-C-C-C(=O)-C(-[Br;H0;D1;+0:1])-C-1.[C:2]-[C:3]-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[C:7]>>[Br;H0;D1;+0:1]-[CH;D3;+0:4](-[C:3]-[C:2])-[C:5](=[O;D1;H0:6])-[C:7] | null | [] | null | null | null | null | The bromination of 3,3-dimethyl-4-phenyl-cyclohexanone takes place in a manner similar to that described above for the preparation of 2-bromo-4-isopropyl-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ketone | Secondary halide | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1.c1ccccc1 | HO- | null | null | null | CC(C)C1CCC(=O)C(Br)C1.CC1(C)CC(=O)CCC1c1ccccc1>>CC1(C)CC(=O)C(Br)CC1c1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-471a2517555541d38d29395f8a35a9fa | CC1=CC(=O)CCC1c1ccccc1>>CC1(C)CC(=O)CCC1c1ccccc1 | [Cl-].[NH4+].C[Mg]Br.CC1=CC(CCC1C1=CC=CC=C1)=O.[Cl-].[Li+]>>CC1(CC(CCC1C1=CC=CC=C1)=O)C | [CH3:1][C:2]1=[CH:4][C:5](=[O:6])[CH2:7][CH2:8][CH:9]1[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[O:6])[CH2:7][CH2:8][CH:9]1[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | CC1=CC(=O)CCC1c1ccccc1 | CC1(C)CC(=O)CCC1c1ccccc1 | null | [Cu](I)I | O1CCCC1 | Miscellaneous | OtherReaction | 6e9787869cd4dbf8690f509ce612084cedf505cb67925714a831178fc724ad8b | f394080031812a9c0cde55fa330311dfe42bea38dbdf0b4621700859838ffa32 | O=C1CCC(c2ccccc2)CC1 | [C;D1;H3:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4](=[O;D1;H0:5])-[C:6]-[C:7]-[C:8]-1-[c:9]>>[C;D1;H3:1]-[C;H0;D4;+0:2]1(-[C;D1;H3:10])-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[C:6]-[C:7]-[C:8]-1-[c:9] | null | [] | 0 | CELSIUS | 10 | MINUTE | Lithium chloride (0.6 mmol) and copper iodide (0.3 mmol) are introduced first under argon in dry tetrahydrofuran (18 ml). At 0° C. 3-methyl-4-phenylcyclohex-2-enone (3 mmol) is added and stirring continues for another 10 min at this temperature. Then a solution of methylmagnesium bromide (3.6 mmol) is slowly added drop... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1=CCCCC1 | C1CCCCC1 | C1CCCCC1.c1ccccc1 | Other | [Cu](I)I.O1CCCC1 | 0 | 0.166667 | CC1=CC(=O)CCC1c1ccccc1>[Cu](I)I.O1CCCC1>CC1(C)CC(=O)CCC1c1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9141ed1670cb49bcba55b96621509c0b | CC1C=C(O[Si](C)(C)C)CCC1.O=C1CCC(=O)N1Br>>CC1CCCC(=O)C1Br | O.BrN1C(CCC1=O)=O.C(C)(=O)[O-].[Na+].C[Si](OC1=CC(CCC1)C)(C)C>>BrC1C(CCCC1C)=O | C[Si](C)(C)[O:7][C:6]1=[CH:8][CH:2]([CH3:1])[CH2:3][CH2:4][CH2:5]1.O=C1CCC(=O)N1[Br:9]>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][C:6](=[O:7])[CH:8]1[Br:9] | CC1C=C(O[Si](C)(C)C)CCC1.O=C1CCC(=O)N1Br | CC1CCCC(=O)C1Br | null | null | C1CCOC1.O.C(C)(=O)OCC | Acylation | OtherReaction | a481869d679e7e55762fb2c18738e6838b013f1f080b79d627d32a9817135bde | a78f0f07701299672b4977dec15f58d03068636e3802f8e034a287b0b3ba65d7 | O=C1CCCCC1 | C-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4](-[C;D1;H3:5])-[C:6]-[C:7]-[C:8]-1.O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:9]>>[Br;H0;D1;+0:9]-[CH;D3;+0:3]1-[C:4](-[C;D1;H3:5])-[C:6]-[C:7]-[C:8]-[C;H0;D3;+0:2]-1=[O;H0;D1;+0:1] | null | [] | null | null | 8 | HOUR | A solution of N-bromosuccinimide (0.48 mmol) and sodium acetate (0.04 mmol) in THF/water (1:1, 5.2 ml) is cooled to 0° C. and trimethyl-(3-methyl-cyclohex-1-enyloxy)-silane (0.4 mmol, 80% pure) is added dropwise. The reaction mixture is heated to room temperature and stirring is continued overnight. After addition of w... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Silyl protective group | Secondary halide.Ketone | C1=CCCCC1.C1CCNC1 | C1CCCCC1 | C1CCCCC1 | HO- | C1CCOC1.O.C(C)(=O)OCC | null | 8 | CC1C=C(O[Si](C)(C)C)CCC1.O=C1CCC(=O)N1Br>C1CCOC1.O.C(C)(=O)OCC>CC1CCCC(=O)C1Br |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-41159f44bf2445e8a3de45b320763f74 | CC(C)C1CCC(=O)C(Br)C1.O=C1CCCCC(c2ccccc2)C1>>O=C1CC(c2ccccc2)CCCC1Br | C1(=CC=CC=C1)C1CC(CCCC1)=O.BrC1C(CCC(C1)C(C)C)=O>>BrC1C(CC(CCC1)C1=CC=CC=C1)=O | CC(C)C1CCC(=O)[CH:14]([Br:15])C1.C1[C:2](=[O:1])[CH2:3][CH:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:11][CH2:12][CH2:13]1>>[O:1]=[C:2]1[CH2:3][CH:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:11][CH2:12][CH2:13][CH:14]1[Br:15] | CC(C)C1CCC(=O)C(Br)C1.O=C1CCCCC(c2ccccc2)C1 | O=C1CC(c2ccccc2)CCCC1Br | null | null | null | C-C Coupling | Bromination | 7365bbbba3204b7e4287acf29931e04384c48688b27647c0716b32f90cb64556 | 11cb2e088c8d020e4df2540bf2d884ae96f339bff038112e13fa7faafee127c0 | O=C1CCCCC(c2ccccc2)C1 | C-C(-C)-C1-C-C-C(=O)-[CH;D3;+0:1](-[Br;D1;H0:2])-C-1.[O;D1;H0:3]=[C;H0;D3;+0:4]1-C-[CH2;D2;+0:5]-[C:6]-[C:7]-[C:8]-[C:9]-1>>[Br;D1;H0:2]-[CH;D3;+0:1]1-[CH2;D2;+0:5]-[C:6]-[C:7]-[C:8]-[C:9]-[C;H0;D3;+0:4]-1=[O;D1;H0:3] | null | [] | null | null | null | null | The bromination of 3-phenylcycloheptanone takes place in a manner similar to that described above for the preparation of 2-bromo-4-isopropyl-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ketone | Secondary halide.Ketone | C1CCCCC1.C1CCCCCC1 | C1CCCCCC1 | C1CCCCCC1.c1ccccc1 | HO- | null | null | null | CC(C)C1CCC(=O)C(Br)C1.O=C1CCCCC(c2ccccc2)C1>>O=C1CC(c2ccccc2)CCCC1Br |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fc11e317df934ddb9fb4ad798f7add3e | CC(C)(C)C1CC(c2ccccc2)CCC1=O.CC(C)(C)C1CCCC(Cl)C1=O>>CC(C)(C)C1CC(c2ccccc2)CC(Cl)C1=O | C(C)(C)(C)C1C(CCC(C1)C1=CC=CC=C1)=O.C(C)(C)(C)C1C(C(CCC1)Cl)=O>>C(C)(C)(C)C1C(C(CC(C1)C1=CC=CC=C1)Cl)=O | CC(C)(C)C1C(=O)C[CH2:14][CH:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:6]1.C1C[CH:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:17](=[O:18])[CH:15]([Cl:16])C1>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH:5]1[CH2:6][CH:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14][CH:15]([Cl:16])[C:17]1=[O:18] | CC(C)(C)C1CC(c2ccccc2)CCC1=O.CC(C)(C)C1CCCC(Cl)C1=O | CC(C)(C)C1CC(c2ccccc2)CC(Cl)C1=O | null | null | null | C-C Coupling | Chlorination | b51efa558fa8fcc06d635bb9582af5d9535e70b2d77b877bfb91954c1bd42275 | 11cb2e088c8d020e4df2540bf2d884ae96f339bff038112e13fa7faafee127c0 | O=C1CCC(c2ccccc2)CC1 | C-C(-C)(-C)-C1-[CH2;D2;+0:1]-[C:2](-[c:3])-[CH2;D2;+0:4]-C-C-1=O.[C;D1;H3:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[CH;D3;+0:9]1-C-C-C-[CH;D3;+0:10](-[Cl;D1;H0:11])-[C:12]-1=[O;D1;H0:13]>>[C;D1;H3:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[CH;D3;+0:9]1-[CH2;D2;+0:1]-[C:2](-[c:3])-[CH2;D2;+0:4]-[CH;D3;+0:10](-[Cl;D1;H0:11])-[C:1... | null | [] | null | null | null | null | The chlorination of 2-tert-butyl-4-phenyl-cyclohexanone takes place in a manner similar to that described above for the preparation of 2-tert-butyl-6-chloro-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ketone | Secondary halide.Ketone | C1CCCCC1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1.c1ccccc1 | HO- | null | null | null | CC(C)(C)C1CC(c2ccccc2)CCC1=O.CC(C)(C)C1CCCC(Cl)C1=O>>CC(C)(C)C1CC(c2ccccc2)CC(Cl)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-03928dba07064fd18db97805e1109e87 | C[Si](C)(C)Cl.O=C1CCC(c2ccccc2)CC1>>C[Si](C)(C)OC1=CCC(c2ccccc2)CC1 | C[Si](Cl)(C)C.C1(=CC=CC=C1)C1CCC(CC1)=O.[I-].[Na+].C(C)N(CC)CC>>C[Si](OC1=CCC(CC1)C1=CC=CC=C1)(C)C | Cl[Si:2]([CH3:1])([CH3:3])[CH3:4].[O:5]=[C:6]1[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[O:5][C:6]1=[CH:7][CH2:8][CH:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1 | C[Si](C)(C)Cl.O=C1CCC(c2ccccc2)CC1 | C[Si](C)(C)OC1=CCC(c2ccccc2)CC1 | null | null | C(C)#N.CCCCCC.CCCCC | Acylation | OtherReaction | c546ff80aa8a81a3553de18a32f290b2242c2a5eb1cf5fc907626eb083315130 | c13dd54c2034fa9746e04e6d624199b4092538f90a428225c0e821f09d4466f2 | C1=CCC(c2ccccc2)CC1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[O;H0;D1;+0:5]=[C;H0;D3;+0:6]1-[C:7]-[C:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-1>>[C;D1;H3:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3])(-[C;D1;H3:4])-[O;H0;D2;+0:5]-[C;H0;D3;+0:6]1=[CH;D2;+0:11]-[C:10]-[C:9]-[C:8]-[C:7]-1 | 73 | [{"value": 73.0, "product": "C[Si](OC1=CCC(CC1)C1=CC=CC=C1)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.0, "product": "C[Si](OC1=CCC(CC1)C1=CC=CC=C1)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | sodium iodide (12.4 mmol) dissolved in acetonitrile (12.4 ml), is added dropwise at room temperature to a solution of 4-phenylcyclohexanone (10 mmol) in hexane (10 ml), followed by triethylamine (12.4 mmol) and trimethylchlorosilane (12.4 mmol). After stirring for two hours cold pentane and ice water are added. The aqu... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Silyl protective group | Silyl protective group | C1CCCCC1 | C1=CCCCC1 | C1=CCCCC1.c1ccccc1 | HCl | C(C)#N.CCCCCC.CCCCC | null | null | C[Si](C)(C)Cl.O=C1CCC(c2ccccc2)CC1>C(C)#N.CCCCCC.CCCCC>C[Si](C)(C)OC1=CCC(c2ccccc2)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1b1a75c210864a4abfc772d05a463448 | CC(C)(C)Cl.C[Si](C)(C)OC1=CCC(c2ccccc2)CC1>>CC(C)(C)C1CC(c2ccccc2)CCC1=O | C[Si](OC1=CCC(CC1)C1=CC=CC=C1)(C)C.C(C)(C)(C)Cl>>C(C)(C)(C)C1C(CCC(C1)C1=CC=CC=C1)=O | Cl[C:2]([CH3:1])([CH3:3])[CH3:4].C[Si](C)(C)[O:17][C:16]1=[CH:5][CH2:6][CH:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14][CH2:15]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[CH:5]1[CH2:6][CH:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14][CH2:15][C:16]1=[O:17] | CC(C)(C)Cl.C[Si](C)(C)OC1=CCC(c2ccccc2)CC1 | CC(C)(C)C1CC(c2ccccc2)CCC1=O | null | [Ti](Cl)(Cl)(Cl)Cl | ClCCl | Acylation | OtherReaction | 5875392a1e05762f5c26dcde040685a5624b03e73e17e34a8cd84896d2efbebd | 198da26d2d214228ef26ebe592c47a799ebcc514fa0271e738a12e899c91f3aa | O=C1CCC(c2ccccc2)CC1 | C-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[C:5]-[C:6]-[C:7]-1.Cl-[C;H0;D4;+0:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11]>>[C;D1;H3:9]-[C;H0;D4;+0:8](-[C;D1;H3:10])(-[C;D1;H3:11])-[CH;D3;+0:3]1-[C:4]-[C:5]-[C:6]-[C:7]-[C;H0;D3;+0:2]-1=[O;H0;D1;+0:1] | 15 | [{"value": 15.0, "product": "C(C)(C)(C)C1C(CCC(C1)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.9, "product": "C(C)(C)(C)C1C(CCC(C1)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -45 | CELSIUS | 3 | HOUR | Trimethyl-(4-phenyl-cyclohex-1-enyloxy)-silane (7.27 mmol) and tert-butyl chloride (7.85 mmol) are introduced first in dichloromethane under nitrogen and cooled to −45° C. A solution, also cooled to −45° C., of titanium tetrachloride (7.63 mmol) in dichloromethane (3.6 ml) is added, and stirring is continued for 3 hour... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Silyl protective group | Ketone | C1=CCCCC1 | C1CCCCC1 | C1CCCCC1.c1ccccc1 | HCl | [Ti](Cl)(Cl)(Cl)Cl.ClCCl | -45 | 3 | CC(C)(C)Cl.C[Si](C)(C)OC1=CCC(c2ccccc2)CC1>[Ti](Cl)(Cl)(Cl)Cl.ClCCl>CC(C)(C)C1CC(c2ccccc2)CCC1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-036640b60e664529845661e0ac98e940 | CC(C)(C)OC(=O)N1CCC(=O)C(Br)C1.NC(=S)N=C(N)N>>CC(C)(C)OC(=O)N1CCc2nc(NC(=N)N)sc2C1 | C(C)(C)(C)OC(=O)N1CC(C(CC1)=O)Br.C(=NC(=S)N)(N)N>>C(C)(C)(C)OC(=O)N1CC2=C(CC1)N=C(S2)NC(=N)N | O=[C:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:20][CH:19]1Br.[NH2:12][C:13]([N:14]=[C:15]([NH2:16])[NH2:17])=[S:18]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[n:12][c:13]([NH:14][C:15](=[NH:16])[NH2:17])[s:18][c:19]2[CH2:20]1 | CC(C)(C)OC(=O)N1CCC(=O)C(Br)C1.NC(=S)N=C(N)N | CC(C)(C)OC(=O)N1CCc2nc(NC(=N)N)sc2C1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 5cea5d5589d3f2de45b3ba7ec47b5e558a8868c8682c72dc7a9a0e3094417287 | b2acdbda34ff0f9c191e84f29366b133b5877f45419e401e78a1fee07acd5878 | c1nc2c(s1)CNCC2 | Br-[CH;D3;+0:1]1-[C:2]-[#7:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[C:11]-[C:12]-[C;H0;D3;+0:13]-1=O.[N;D1;H2:14]-[C;H0;D3;+0:15](-[NH2;D1;+0:16])=[N;H0;D2;+0:17]-[C;H0;D3;+0:18](-[NH2;D1;+0:19])=[S;H0;D1;+0:20]>>[C;D1;H3:8]-[C:7](-[C;D1;H3:9])(-[C;D1;H3:10])-[#8:6]-[C:4](=[O;D1;H... | null | [] | null | null | null | null | Analogously to the preparation of Example C-01, 3-bromo-4-oxo-piperidine-1-carboxylic acid tert-butyl ester is reacted with 2-imino-4-thiobiuret to form the title compound. tR 2.55 min (LC-1); ESI-MS (+): m/z 298.25 [M+H]+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Thioamide.Primary amine | Secondary amine | C1CC[NH]CC1 | c1nc2c(s1)C[NH]CC2 | c1nc2c(s1)C[NH]CC2 | HBr | null | null | null | CC(C)(C)OC(=O)N1CCC(=O)C(Br)C1.NC(=S)N=C(N)N>>CC(C)(C)OC(=O)N1CCc2nc(NC(=N)N)sc2C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0f91e36356c443afb325cec8d55ab4f8 | CC(C)(C)OC(=O)N1CCC(=O)CC1.CC(C)C1CCC(=O)C(Br)C1>>CC(C)(C)OC(=O)N1CCC(=O)C(Br)C1 | C(C)(C)(C)OC(=O)N1CCC(CC1)=O.BrC1C(CCC(C1)C(C)C)=O>>C(C)(C)(C)OC(=O)N1CC(C(CC1)=O)Br | O=C1C[CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:15]C1.CC(C)C1C[CH2:10][C:11](=[O:12])[CH:13]([Br:14])C1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C:11](=[O:12])[CH:13]([Br:14])[CH2:15]1 | CC(C)(C)OC(=O)N1CCC(=O)CC1.CC(C)C1CCC(=O)C(Br)C1 | CC(C)(C)OC(=O)N1CCC(=O)C(Br)C1 | null | null | null | C-C Coupling | Bromination | aea0acfa117d7c4a03b08dd8506eaaa376262fbddf747715f7e8138114b57118 | 11cb2e088c8d020e4df2540bf2d884ae96f339bff038112e13fa7faafee127c0 | O=C1CCNCC1 | C-C(-C)-C1-C-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH;D3;+0:4](-[Br;D1;H0:5])-C-1.O=C1-C-[CH2;D2;+0:6]-[#7:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[C;D1;H3:14])-[CH2;D2;+0:15]-C-1>>[Br;D1;H0:5]-[CH;D3;+0:4]1-[CH2;D2;+0:6]-[#7:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])... | null | [] | null | null | null | null | The bromination of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester takes place in a manner similar to that described above for the preparation of 2-bromo-4-isopropyl-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ketone | Secondary halide.Ketone | C1CC[NH]CC1.C1CCCCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(=O)CC1.CC(C)C1CCC(=O)C(Br)C1>>CC(C)(C)OC(=O)N1CCC(=O)C(Br)C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6b14da6e27204bad9338c2861405d99d | CCCCCCBr.N=C(N)Nc1nc2c(s1)CNCC2>>CCCCCCN1CCc2nc(NC(=N)N)sc2C1 | [OH-].[Na+].BrCCCCCC.N1=C(SC=2CNCCC21)NC(=N)N.C([O-])([O-])=O.[Cs+].[Cs+]>>C(CCCCC)N1CC2=C(CC1)N=C(S2)NC(=N)N | Br[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[NH:7]1[CH2:8][CH2:9][c:10]2[n:11][c:12]([NH:13][C:14](=[NH:15])[NH2:16])[s:17][c:18]2[CH2:19]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][c:10]2[n:11][c:12]([NH:13][C:14](=[NH:15])[NH2:16])[s:17][c:18]2[CH2:19]1 | CCCCCCBr.N=C(N)Nc1nc2c(s1)CNCC2 | CCCCCCN1CCc2nc(NC(=N)N)sc2C1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 290a75043f02ceb73ce8bdfbb1586e5817477e9af0d250975dbae2585f752260 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1nc2c(s1)CNCC2 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#16;a:4]:[c:5]1:[c:6](:[#7;a:7])-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-1>>[#16;a:4]:[c:5]1:[c:6](:[#7;a:7])-[C:8]-[C:9]-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:11]-1 | null | [] | null | null | 8 | HOUR | 1-bromohexane (0.11 mmol) is added to a suspension of N-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-yl)-guanidine (0.1 mmol) and caesium carbonate (0.22 mmol) in dimethylformamide (0.3 ml) and the reaction mixture is stirred overnight at room temperature. After adding 2M caustic soda solution (1 ml) the mixture is ex... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1nc2c(s1)CNCC2 | c1nc2c(s1)C[NH]CC2 | c1nc2c(s1)C[NH]CC2 | HBr | CN(C=O)C | null | 8 | CCCCCCBr.N=C(N)Nc1nc2c(s1)CNCC2>CN(C=O)C>CCCCCCN1CCc2nc(NC(=N)N)sc2C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d99e3ad127f8439ba0849a80a747879b | CCOC(=O)CCCCBr.CCOC(=O)CNCc1ccccc1>>CCOC(=O)CN(CCCCC(=O)O)Cc1ccccc1 | C(C)OC(CNCC1=CC=CC=C1)=O.C(C)OC(CCCCBr)=O.C([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)N(CCCCC(=O)O)CC(=O)OCC | CC[O:14][C:12]([CH2:11][CH2:10][CH2:9][CH2:8]Br)=[O:13].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]([CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[OH:14])[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | CCOC(=O)CCCCBr.CCOC(=O)CNCc1ccccc1 | CCOC(=O)CN(CCCCC(=O)O)Cc1ccccc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | d413f33705c3e77047c09232275aeff77dadbf668076df5e59ef9ae9126c6b77 | f2a50574915429f7b0a010ed2814b76ae640dbd3c0189b7c1be6ccb9f276d2cb | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-C-C.[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C:12]-[NH;D2;+0:13]-[C:14]-[c:15]>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C:12]-[N;H0;D3;+0:13](-[C:14]-[c:15])-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7] | 30 | [{"value": 30.0, "product": "C(C1=CC=CC=C1)N(CCCCC(=O)O)CC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | N-benzylglycine ethyl ester (1.87 ml) and 5-bromovaleric acid ethyl ester (1.92 ml) are dissolved in dimethylformamide (100 ml) and stirred in the presence of potassium carbonate (1.66 g) for 2 days at room temperature. The reaction is quenched with saturated aqueous ammonium chloride solution, and extraction is carrie... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Secondary amine | Carboxylic acid.Tertiary amine | null | null | c1ccccc1 | HBr | CN(C=O)C | null | null | CCOC(=O)CCCCBr.CCOC(=O)CNCc1ccccc1>CN(C=O)C>CCOC(=O)CN(CCCCC(=O)O)Cc1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4e89e4efeb0e4d1989b7de63082ffaf5 | CCOC(=O)CN(CCCCC(=O)O)Cc1ccccc1>>O=C1CCCCN(Cc2ccccc2)C1 | CC(C)(C)[O-].[K+].C(C1=CC=CC=C1)N(CCCCC(=O)O)CC(=O)OCC.Cl>>C(C1=CC=CC=C1)N1CC(CCCC1)=O | CCOC(=O)[CH2:15][N:7]([CH2:6][CH2:5][CH2:4][CH2:3][C:2](O)=[O:1])[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH2:5][CH2:6][N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1 | CCOC(=O)CN(CCCCC(=O)O)Cc1ccccc1 | O=C1CCCCN(Cc2ccccc2)C1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | e84f4305450d5bdda7d0015fd1e58943e82ab3396324f780f5869c9b6566bb1b | d5654c9a84fc42e383a200090b60ea1c499fce894824745135207b080d8463d3 | O=C1CCCCN(Cc2ccccc2)C1 | C-C-O-C(=O)-[CH2;D2;+0:1]-[#7:2](-[C:3])-[C:4].O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C:7]-[C:8]>>[C:8]-[C:7]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[CH2;D2;+0:1]-[#7:2](-[C:4])-[C:3] | 45 | [{"value": 45.0, "product": "C(C1=CC=CC=C1)N1CC(CCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.9, "product": "C(C1=CC=CC=C1)N1CC(CCCC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of potassium tert-butylate (336 mg) in toluene (2.5 ml) is refluxed for 10 min. Then 5-(benzyl-ethoxycarbonylmethyl-amino)-pentanoic acid (695 mg) in toluene (1 ml) is slowly added to the suspension and when the addition is complete the mixture is refluxed for another 1.5 hours. After cooling to room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ketone | null | C1CCC[NH]CC1 | C1CCC[NH]CC1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | CCOC(=O)CN(CCCCC(=O)O)Cc1ccccc1>C1(=CC=CC=C1)C>O=C1CCCCN(Cc2ccccc2)C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e2c1f42674774ba8814ec0d8b095ea7e | CC(C)C1CCC(=O)C(Br)C1.O=C1CCCCN(Cc2ccccc2)C1>>O=C1CN(Cc2ccccc2)CCCC1Br | C(C1=CC=CC=C1)N1CC(CCCC1)=O.BrC1C(CCC(C1)C(C)C)=O>>C(C1=CC=CC=C1)N1CC(C(CCC1)Br)=O | CC(C)C1CCC(=O)C([Br:16])C1.[O:1]=[C:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13][CH2:14][CH2:15]1>>[O:1]=[C:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13][CH2:14][CH:15]1[Br:16] | CC(C)C1CCC(=O)C(Br)C1.O=C1CCCCN(Cc2ccccc2)C1 | O=C1CN(Cc2ccccc2)CCCC1Br | null | null | null | Functional Group Interconversion | Bromination | 6f7f5d308be3c2af8f2cc07bf9302c3832c5a317d5b8f8e7b3f3ced339724fcb | af6f895a0e88516f0a2e7e54838a1e72c142a95d71091e6b02ff568a7310f7ea | O=C1CCCCN(Cc2ccccc2)C1 | C-C(-C)-C1-C-C-C(=O)-C(-[Br;H0;D1;+0:1])-C-1.[#7:2]-[C:3]-[C:4](=[O;D1;H0:5])-[CH2;D2;+0:6]-[C:7]-[C:8]>>[#7:2]-[C:3]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6](-[Br;H0;D1;+0:1])-[C:7]-[C:8] | null | [] | null | null | null | null | The bromination of 1-benzyl-azepan-3-one takes place in a manner similar to that described above for the preparation of 2-bromo-4-isopropyl-cyclohexanone. The title compound is reacted as a crude product without further characterization.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ketone | Secondary halide | C1CCCCC1.C1CCC[NH]CC1 | C1CCC[NH]CC1 | C1CCC[NH]CC1.c1ccccc1 | HO- | null | null | null | CC(C)C1CCC(=O)C(Br)C1.O=C1CCCCN(Cc2ccccc2)C1>>O=C1CN(Cc2ccccc2)CCCC1Br |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-98496fd20a5141068171bd4a1a3cc0ec | CCCCC(=O)Cl.N=C(N)Nc1nc2c(s1)CNCC2>>CCCCC(=O)C1NCCc2nc(NC(=N)N)sc21 | [OH-].[Na+].C(C)(C)N(CC)C(C)C.C(CCCC)(=O)Cl.Cl.Cl.N1=C(SC=2CNCCC21)NC(=N)N>>C(CCCC)(=O)C1NCCC2=C1SC(=N2)NC(=N)N | Cl[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[O:6].[CH2:7]1[NH:8][CH2:9][CH2:10][c:11]2[n:12][c:13]([NH:14][C:15](=[NH:16])[NH2:17])[s:18][c:19]21>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[CH:7]1[NH:8][CH2:9][CH2:10][c:11]2[n:12][c:13]([NH:14][C:15](=[NH:16])[NH2:17])[s:18][c:19]21 | CCCCC(=O)Cl.N=C(N)Nc1nc2c(s1)CNCC2 | CCCCC(=O)C1NCCc2nc(NC(=N)N)sc21 | null | null | CN(C=O)C.C(C)(=O)OCC | C-C Coupling | OtherReaction | 75cc5138054c1653c7535a76b156114150152377d8fb19daf76c40ae14cca432 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1nc2c(s1)CNCC2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#16;a:5]1:[c:6]:[#7;a:7]:[c:8]2:[c:9]:1-[CH2;D2;+0:10]-[#7:11]-[C:12]-[C:13]-2>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:10]1-[#7:11]-[C:12]-[C:13]-[c:8]2:[#7;a:7]:[c:6]:[#16;a:5]:[c:9]:2-1 | null | [] | null | null | 16 | HOUR | Diisopropylethylamine (0.22 mmol) and then pentanoyl chloride (0.11 mmol) are added to a stirred suspension of N-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-yl)-guanidine-dihydrochloride (0.1 mmol) in dimethylformamide (0.7 ml) and the reaction mixture is stirred for another 16 hours at room temperature. After the ad... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1nc2c(s1)CNCC2 | c1nc2c(s1)CNCC2 | c1nc2c(s1)CNCC2 | HCl | CN(C=O)C.C(C)(=O)OCC | null | 16 | CCCCC(=O)Cl.N=C(N)Nc1nc2c(s1)CNCC2>CN(C=O)C.C(C)(=O)OCC>CCCCC(=O)C1NCCc2nc(NC(=N)N)sc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fecbe090558448a4a06f30a565bfc4fc | C=CCC(=O)O.N=C(N)Nc1nc2c(s1)CNCC2>>C=CCC(=O)N1CCc2nc(NC(=N)N)sc2C1 | C(C)(C)N(CC)C(C)C.C(=C)CC(=O)O.N1N=NC2=C1C=CC=C2O[P+](N(C)C)(N(C)C)N(C)C.F[P-](F)(F)(F)(F)F.Cl.Cl.N1=C(SC=2CNCCC21)NC(=N)N.[OH-].[Na+]>>C(CC=C)(=O)N1CC2=C(CC1)N=C(S2)NC(=N)N | O[C:4]([CH2:3][CH:2]=[CH2:1])=[O:5].[NH:6]1[CH2:7][CH2:8][c:9]2[n:10][c:11]([NH:12][C:13](=[NH:14])[NH2:15])[s:16][c:17]2[CH2:18]1>>[CH2:1]=[CH:2][CH2:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][c:9]2[n:10][c:11]([NH:12][C:13](=[NH:14])[NH2:15])[s:16][c:17]2[CH2:18]1 | C=CCC(=O)O.N=C(N)Nc1nc2c(s1)CNCC2 | C=CCC(=O)N1CCc2nc(NC(=N)N)sc2C1 | null | null | CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 0b838e10b717562930e503a5fd1978a0641969d19d05c0e1b262f037b0d69d5b | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1nc2c(s1)CNCC2 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]=[C;D1;H2:5].[#16;a:6]:[c:7]1:[c:8](:[#7;a:9])-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-1>>[#16;a:6]:[c:7]1:[c:8](:[#7;a:9])-[C:10]-[C:11]-[N;H0;D3;+0:12](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]=[C;D1;H2:5])-[C:13]-1 | null | [] | null | null | 16 | HOUR | Diisopropylethylamine (0.22 mmol), vinyl acetic acid (0.11 mmol) and benzotriazolyloxy-tris-(dimethylamino)phosphonium-hexafluorophosphate (0.11 mmol) are added successively to a stirred suspension of N-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-yl)-guanidine-dihydrochloride (0.1 mmol) in dimethylformamide (0.7 mL),... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | c1nc2c(s1)CNCC2 | c1nc2c(s1)C[NH]CC2 | c1nc2c(s1)C[NH]CC2 | HO- | CN(C=O)C | null | 16 | C=CCC(=O)O.N=C(N)Nc1nc2c(s1)CNCC2>CN(C=O)C>C=CCC(=O)N1CCc2nc(NC(=N)N)sc2C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a03797be0d6c4f4e9452b66eee9f31f0 | N=C(N)Nc1nc2c(s1)CNCC2.O=C(Cl)OCc1ccccc1>>N=C(N)Nc1nc2c(s1)CN(C(=O)OCc1ccccc1)CC2 | C([O-])([O-])=O.[Na+].[Na+].ClC(=O)OCC1=CC=CC=C1.N1=C(SC=2CNCCC21)NC(=N)N.C(C)(C)N(CC)C(C)C>>C(C1=CC=CC=C1)OC(=O)N1CC2=C(CC1)N=C(S2)NC(=N)N | [NH:1]=[C:2]([NH2:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([s:9]1)[CH2:10][NH:11][CH2:22][CH2:23]2.Cl[C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[NH:1]=[C:2]([NH2:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([s:9]1)[CH2:10][N:11]([C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[CH2:22][... | N=C(N)Nc1nc2c(s1)CNCC2.O=C(Cl)OCc1ccccc1 | N=C(N)Nc1nc2c(s1)CN(C(=O)OCc1ccccc1)CC2 | null | null | CN(C=O)C.C(C)(=O)OCC | Protection | N-alkylation of secondary amines with alkyl halides | b566cbd89ee088029ba250e0972f43d9e855ace743b5f8322802597d49dc36db | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | O=C(OCc1ccccc1)N1CCc2ncsc2C1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#16;a:5]:[c:6]1:[c:7](:[#7;a:8])-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-1>>[#16;a:5]:[c:6]1:[c:7](:[#7;a:8])-[C:9]-[C:10]-[N;H0;D3;+0:11](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4])-[C:12]-1 | null | [] | null | null | 3 | HOUR | Benzyl chloroformate is added to a stirred suspension of N-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-yl)-guanidine (0.1 mmol) and diisopropylethylamine (0.22 mmol) in dimethylformamide (0.7 ml) and the mixture is stirred for another 3 hours at room temperature. After the addition of saturated aqueous sodium carbona... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | c1nc2c(s1)CNCC2 | c1nc2c(s1)C[NH]CC2 | c1nc2c(s1)C[NH]CC2.c1ccccc1 | HCl | CN(C=O)C.C(C)(=O)OCC | null | 3 | N=C(N)Nc1nc2c(s1)CNCC2.O=C(Cl)OCc1ccccc1>CN(C=O)C.C(C)(=O)OCC>N=C(N)Nc1nc2c(s1)CN(C(=O)OCc1ccccc1)CC2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-878a69e41b514e08afeac88bdd502b76 | N=C(N)Nc1nc2c(s1)CNCC2.O=C=Nc1ccccc1>>N=C(N)Nc1nc2c(s1)CN(C(=O)Nc1ccccc1)CC2 | C1(=CC=CC=C1)N=C=O.Cl.Cl.N1=C(SC=2CNCCC21)NC(=N)N.C([O-])([O-])=O.[Na+].[Na+].C(C)(C)N(CC)C(C)C>>C1(=CC=CC=C1)NC(=O)N1CC2=C(CC1)N=C(S2)NC(=N)N | [NH:1]=[C:2]([NH2:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([s:9]1)[CH2:10][NH:11][CH2:21][CH2:22]2.[C:12](=[O:13])=[N:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[NH:1]=[C:2]([NH2:3])[NH:4][c:5]1[n:6][c:7]2[c:8]([s:9]1)[CH2:10][N:11]([C:12](=[O:13])[NH:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[CH2:21][CH2:22]2 | N=C(N)Nc1nc2c(s1)CNCC2.O=C=Nc1ccccc1 | N=C(N)Nc1nc2c(s1)CN(C(=O)Nc1ccccc1)CC2 | null | null | CN(C=O)C | Acylation | Urea synthesis via isocyanate and secondary amine | 8cd91400c2e1a663d0576c91f93232ba5df262390560130f8c98d4511422f4d6 | 5272a383a93723269f1934f97993b0175b43cd993bcdf2f45add1dbb852d1e09 | O=C(Nc1ccccc1)N1CCc2ncsc2C1 | [#16;a:1]:[c:2]1:[c:3](:[#7;a:4])-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-1.[O;D1;H0:9]=[C;H0;D2;+0:10]=[N;H0;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[#16;a:1]:[c:2]1:[c:3](:[#7;a:4])-[C:5]-[C:6]-[N;H0;D3;+0:7](-[C;H0;D3;+0:10](=[O;D1;H0:9])-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[C:8]-1 | null | [] | null | null | 3 | HOUR | Diisopropylethylamine (0.2 mmol) and, after 5 min, phenyl isocyanate (0.11 mmol) are added to a suspension of N-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-yl)-guanidine dihydrochloride (0.1 mmol) in dimethylformamide (0.5 ml). The reaction mixture is stirred for another 3 hours at room temperature. Then saturated aq... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amine | Urea | c1nc2c(s1)CNCC2 | c1nc2c(s1)C[NH]CC2 | c1nc2c(s1)C[NH]CC2.c1ccccc1 | null | CN(C=O)C | null | 3 | N=C(N)Nc1nc2c(s1)CNCC2.O=C=Nc1ccccc1>CN(C=O)C>N=C(N)Nc1nc2c(s1)CN(C(=O)Nc1ccccc1)CC2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5d651716a5334dd585a5829f7b39f916 | CC(C)I.O=c1cc(C(F)(F)F)c2cc([N+](=O)[O-])ccc2[nH]1>>CC(C)Oc1cc(C(F)(F)F)c2cc(N)ccc2n1 | FC(C1=CC(NC2=CC=C(C=C12)[N+](=O)[O-])=O)(F)F.[F-].[Cs+].IC(C)C>>NC=1C=C2C(=CC(=NC2=CC1)OC(C)C)C(F)(F)F | I[CH:2]([CH3:1])[CH3:3].O=[N+:15]([O-])[c:14]1[cH:13][c:12]2[c:7]([C:8]([F:9])([F:10])[F:11])[cH:6][c:5](=[O:4])[nH:19][c:18]2[cH:17][cH:16]1>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[c:12]2[cH:13][c:14]([NH2:15])[cH:16][cH:17][c:18]2[n:19]1 | CC(C)I.O=c1cc(C(F)(F)F)c2cc([N+](=O)[O-])ccc2[nH]1 | CC(C)Oc1cc(C(F)(F)F)c2cc(N)ccc2n1 | null | null | CN(C)C=O | Functional Group Interconversion | OtherReaction | 96a3ae3ff20da279c9c8f69949c865da38ffaf99aead00d4e3a432672ba90e1a | 9783a2ae5121f50ea19ae067cb089d41d544d2877f024cc090ab114b831bf950 | c1ccc2ncccc2c1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].O=[N+;H0;D3:4](-[O-])-[c:5]1:[c:6]:[c:7]2:[c:8]:[c:9]:[c;H0;D3;+0:10](=[O;H0;D1;+0:11]):[nH;D2;+0:12]:[c:13]:2:[c:14]:[c:15]:1>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[O;H0;D2;+0:11]-[c;H0;D3;+0:10]1:[c:9]:[c:8]:[c:7]2:[c:6]:[c:5](-[NH2;D1;+0:4]):[c:15]:[c:14]:[c:13]:2:[n;H0;D2;... | 99.9 | [{"value": 90.0, "product": "NC=1C=C2C(=CC(=NC2=CC1)OC(C)C)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.9, "product": "NC=1C=C2C(=CC(=NC2=CC1)OC(C)C)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | In a 250-mL r.b. flask, a solution of 4-trifluoromethyl-6-nitroquinolinone (structure 1 of Scheme I) (3.78 g, 14.6 mmol) in DMF (75 mL) was treated with CsF (12.41 g, 73 mmol, 5.0 equiv.) and 2-iodopropane (11.09 g, 73 mmol, 5.0 equiv). The reaction mixture was stirred at room temperature (rt) for 18 h. The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Nitro group | Ether.Primary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | I- | CN(C)C=O | null | 18 | CC(C)I.O=c1cc(C(F)(F)F)c2cc([N+](=O)[O-])ccc2[nH]1>CN(C)C=O>CC(C)Oc1cc(C(F)(F)F)c2cc(N)ccc2n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-400cdce93deb4c6eb318c93910679f8e | NN.Nc1ccc2[nH]c(=O)cc(C(F)(F)F)c2c1>>NNc1ccc2[nH]c(=O)cc(C(F)(F)F)c2c1 | NN.N(=O)[O-].[Na+].NC=1C=C2C(=CC(NC2=CC1)=O)C(F)(F)F.O.O.Cl[Sn]Cl>>N(N)C=1C=C2C(=CC(NC2=CC1)=O)C(F)(F)F | N[NH2:1].[NH2:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8](=[O:9])[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[c:16]2[cH:17]1>>[NH2:1][NH:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8](=[O:9])[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[c:16]2[cH:17]1 | NN.Nc1ccc2[nH]c(=O)cc(C(F)(F)F)c2c1 | NNc1ccc2[nH]c(=O)cc(C(F)(F)F)c2c1 | null | null | O.Cl | Miscellaneous | OtherReaction | bff6efaab43fcaa1734c9c2b1bb92dedefa785fd0e1362752739094a114b1a2d | edabab25c27777c2204ef93ae7e0a2367d16ed129319c92fb41548ddcbd38608 | O=c1ccc2ccccc2[nH]1 | N-[NH2;D1;+0:1].[NH2;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[NH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | -1 | CELSIUS | 1 | HOUR | In a 250 mL r.b. flask a suspension of 6-amino-4-trifluoromethylquinolin-2(1H)-one (structure 8 of Scheme II, where R1=trifluoromethyl) (2.28 g, 10 mmol) in 10 mL conc. HCl was cooled to −1° C. and a solution of NaNO2 (0.40 g, 12 mmol) in water (5 mL) was added dropwise in 20 min. The dark yellow suspension was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary amine | Hydrazine | null | null | c1ccc2ncccc2c1 | Other | O.Cl | -1 | 1 | NN.Nc1ccc2[nH]c(=O)cc(C(F)(F)F)c2c1>O.Cl>NNc1ccc2[nH]c(=O)cc(C(F)(F)F)c2c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8a9091e348c5446da72de839ee69dbae | CCCN1c2cc3c(C(F)(F)F)cc(=O)[nH]c3cc2CCC1C.O=CC1CC1>>CC1CCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc2N1CC1CC1 | FC(C1=CC(NC2=CC=3CCC(N(C3C=C21)CCC)C)=O)(F)F.C1(CC1)C=O>>FC(C1=CC(NC2=CC=3CCC(N(C3C=C21)CC2CC2)C)=O)(F)F | CCC[N:20]1[CH:2]([CH3:1])[CH2:3][CH2:4][c:5]2[cH:6][c:7]3[nH:8][c:9](=[O:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[c:17]3[cH:18][c:19]21.O=[CH:21][CH:22]1[CH2:23][CH2:24]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]3[nH:8][c:9](=[O:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[c:17]3[cH:18][c:19]2[N:20]1[CH2... | CCCN1c2cc3c(C(F)(F)F)cc(=O)[nH]c3cc2CCC1C.O=CC1CC1 | CC1CCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc2N1CC1CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a7f7479928e5995278513189ca3eeee8f9be3deb4e93b7b07cc34795d8b5f4e7 | 2db92e8910de3b0427c118b680e1a0a612a1520e71fb0f87110d867c18814b86 | O=c1ccc2cc3c(cc2[nH]1)CCCN3CC1CC1 | C-C-C-[N;H0;D3;+0:1](-[C:2](-[C;D1;H3:3])-[C:4])-[c:5](:[c:6]):[c:7].O=[CH;D2;+0:8]-[C:9]1-[C:10]-[C:11]-1>>[C:4]-[C:2](-[C;D1;H3:3])-[N;H0;D3;+0:1](-[CH2;D2;+0:8]-[C:9]1-[C:10]-[C:11]-1)-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | This compound was prepared in a similar fashion as that described in Example 84 from Compound 187 (Structure 33 of Scheme VI, where R1=methyl, n=1) and cyclopropanecarboxaldehyde. 1H NMR (400 MHz, CDCl3) 10.91 (br. s, 1H), 7.14 (s, 1H), 7.01 (s, 1H), 6.94 (s, 1H), 3.65 (m, 1H), 3.35 (dd, 1H, J=15.0, 5.5), 3.09 (dd, 1H,... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Tertiary amine | Tertiary amine | c1ccc2cc3c(cc2n1)CC[CH]N3 | c1ccc2cc3c(cc2n1)CC[CH]N3 | c1ccc2cc3c(cc2n1)CC[CH]N3.C1CC1 | HO- | null | null | null | CCCN1c2cc3c(C(F)(F)F)cc(=O)[nH]c3cc2CCC1C.O=CC1CC1>>CC1CCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc2N1CC1CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c83558528a69411cbdd1d98c6c51341f | CC1CCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc2N1CC1CC1>>CCN1c2cc3c(C(F)(F)F)cc(=O)[nH]c3cc2CCC1C | FC(C1=CC(NC2=CC=3CCC(N(C3C=C21)CC2CC2)C)=O)(F)F.C(C)=O>>FC(C1=CC(NC2=CC=3CCC(N(C3C=C21)CC)C)=O)(F)F | C1C[CH:1]1[CH2:2][N:3]1[c:4]2[cH:5][c:6]3[c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][c:13](=[O:14])[nH:15][c:16]3[cH:17][c:18]2[CH2:19][CH2:20][CH:21]1[CH3:22]>>[CH3:1][CH2:2][N:3]1[c:4]2[cH:5][c:6]3[c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][c:13](=[O:14])[nH:15][c:16]3[cH:17][c:18]2[CH2:19][CH2:20][CH:21]1[CH3:22] | CC1CCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc2N1CC1CC1 | CCN1c2cc3c(C(F)(F)F)cc(=O)[nH]c3cc2CCC1C | null | null | null | Miscellaneous | OtherReaction | 703b19d9df1584a8849062009d9c34e1e955a1167cfa5924ffef1ba1358b7e81 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=c1ccc2cc3c(cc2[nH]1)CCCN3 | [#7:1]-[C:2]-[CH;D3;+0:3]1-C-C-1>>[#7:1]-[C:2]-[CH3;D1;+0:3] | null | [] | null | null | null | null | This compound was prepared in a similar fashion as that described in Example 84 from Compound 187 (Structure 33 of Scheme VI, where R1=methyl, n=1) and acetaldehyde. 1H NMR (400 MHz, CDCl3) 11.19 (br. s, 1H), 7.11 (s, 1H), 7.00 (s, 1H), 6.80 (s, 1H), 3.55 (m, 1H), 3.47-3.32 (m, 2H), 2.93-2.80 (m, 2H), 1.93-1.79 (m, 2H)... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1CC1 | null | c1ccc2cc3c(cc2n1)CC[CH]N3 | Other | null | null | null | CC1CCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc2N1CC1CC1>>CCN1c2cc3c(C(F)(F)F)cc(=O)[nH]c3cc2CCC1C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-98046a2630464160bd404d70de886952 | CCN1c2cc3c(C(F)(F)F)cc(=O)[nH]c3cc2CCC1C.CCOC(O)C(F)(F)F>>CC1CCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc2N1CC(F)(F)F | FC(C1=CC(NC2=CC=3CCC(N(C3C=C21)CC)C)=O)(F)F.C(C)OC(C(F)(F)F)O>>FC(C1=CC(NC2=CC=3CCC(N(C3C=C21)CC(F)(F)F)C)=O)(F)F | CC[N:20]1[CH:2]([CH3:1])[CH2:3][CH2:4][c:5]2[cH:6][c:7]3[nH:8][c:9](=[O:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[c:17]3[cH:18][c:19]21.CCO[CH:21](O)[C:22]([F:23])([F:24])[F:25]>>[CH3:1][CH:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]3[nH:8][c:9](=[O:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[c:17]3[cH:18][c:19]2[N:20... | CCN1c2cc3c(C(F)(F)F)cc(=O)[nH]c3cc2CCC1C.CCOC(O)C(F)(F)F | CC1CCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc2N1CC(F)(F)F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 61fde9879f7c934dcb2a0ff2ddfdb0a89d53886139ab30be4cbd0f2d64886e26 | 98256710607e1d9b88f97ae6ecaa66242f83220f290bf996d79cc1e54296ee07 | O=c1ccc2cc3c(cc2[nH]1)CCCN3 | C-C-O-[CH;D3;+0:1](-O)-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[F;D1;H0:5].C-C-[N;H0;D3;+0:6](-[C:7](-[C;D1;H3:8])-[C:9])-[c:10](:[c:11]):[c:12]>>[C:9]-[C:7](-[C;D1;H3:8])-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[F;D1;H0:5])-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | This compound was prepared in a similar fashion as that described in Example 84 from Compound 187 (Structure 33 of Scheme VI, where R1=methyl, n=1) and trifluoroacetaldehyde ethyl hemiacetal. 1H NMR (400 MHz, CDCl3) 11.08 (br. s, 1H), 7.06 (s, 1H), 7.00 (s, 1H), 6.99 (s, 1H), 3.99 (m, 1H), 3.81 (m, 1H), 3.67 (m, 1H), 3... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol.Tertiary amine | Tertiary amine | c1ccc2cc3c(cc2n1)CC[CH]N3 | c1ccc2cc3c(cc2n1)CC[CH]N3 | c1ccc2cc3c(cc2n1)CC[CH]N3 | HO- | null | null | null | CCN1c2cc3c(C(F)(F)F)cc(=O)[nH]c3cc2CCC1C.CCOC(O)C(F)(F)F>>CC1CCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc2N1CC(F)(F)F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2a6bbf7ff0534d48a19790d0a4deee4c | CC1CCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc2N1CC(F)(F)F>>O=c1cc(C(F)(F)F)c2cc3c(cc2[nH]1)CCCN3CC(F)(F)F | FC(C1=CC(NC2=CC=3CCC(N(C3C=C21)CC(F)(F)F)C)=O)(F)F.C(C)OC(C(F)(F)F)O>>FC(C1=CC(NC2=CC=3CCCN(C3C=C21)CC(F)(F)F)=O)(F)F | C[CH:18]1[CH2:17][CH2:16][c:12]2[c:11]([cH:10][c:9]3[c:4]([C:5]([F:6])([F:7])[F:8])[cH:3][c:2](=[O:1])[nH:15][c:14]3[cH:13]2)[N:19]1[CH2:20][C:21]([F:22])([F:23])[F:24]>>[O:1]=[c:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[c:9]2[cH:10][c:11]3[c:12]([cH:13][c:14]2[nH:15]1)[CH2:16][CH2:17][CH2:18][N:19]3[CH2:20][C:21]([F:22... | CC1CCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc2N1CC(F)(F)F | O=c1cc(C(F)(F)F)c2cc3c(cc2[nH]1)CCCN3CC(F)(F)F | null | null | null | Miscellaneous | OtherReaction | 423a2f76099ff52bccfb7b6a2e18cdef2ade2cd79e8b14d2af5265ce9eb028b1 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=c1ccc2cc3c(cc2[nH]1)CCCN3 | C-[CH;D3;+0:1](-[C:2]-[C:3])-[#7:4](-[C:5])-[c:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[#7:4](-[C:5])-[c:6] | null | [] | null | null | null | null | This compound was prepared in a similar fashion as that described in Example 84 from Compound 192 (Structure 33 of Scheme VI, where R1═H, n=1) and trifluoroacetaldehyde ethyl hemiacetal. 1H NMR (400 MHz, CDCl3) 11.32 (br. s, 1H), 7.11 (s, 1H), 7.02 (s, 1H), 6.99 (s, 1H), 3.88 (q, 2H, J=8.9), 3.47 (t, 2H, J=5.6), 2.93 (... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2cc3c(cc2n1)CC[CH]N3 | c1ccc2cc3c(cc2n1)CCCN3 | c1ccc2cc3c(cc2n1)CCCN3 | Other | null | null | null | CC1CCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc2N1CC(F)(F)F>>O=c1cc(C(F)(F)F)c2cc3c(cc2[nH]1)CCCN3CC(F)(F)F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-dd2664cfb2f14e25889c755ea373ac67 | CCC=O.O=c1cc(C(F)(F)F)c2cc3c(cc2[nH]1)CCCN3CC(F)(F)F>>CCCN1CCCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc21 | FC(C1=CC(NC2=CC=3CCCN(C3C=C21)CC(F)(F)F)=O)(F)F.C(CC)=O>>FC(C1=CC(NC2=CC=3CCCN(C3C=C21)CCC)=O)(F)F | O=[CH:3][CH2:2][CH3:1].FC(F)(F)C[N:4]1[CH2:5][CH2:6][CH2:7][c:8]2[cH:9][c:10]3[nH:11][c:12](=[O:13])[cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[c:20]3[cH:21][c:22]21>>[CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][CH2:7][c:8]2[cH:9][c:10]3[nH:11][c:12](=[O:13])[cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[c:20]3[cH:21][c:22]2... | CCC=O.O=c1cc(C(F)(F)F)c2cc3c(cc2[nH]1)CCCN3CC(F)(F)F | CCCN1CCCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | aadc8a7a685bf0f8e58d77107392bea77d65ed88586bf090bc79fe11c30a90fa | 17172fd7ba3a9b03249b2b2d84ba9c93c09a94e9e6198021ed6213a54128d638 | O=c1ccc2cc3c(cc2[nH]1)CCCN3 | F-C(-F)(-F)-C-[N;H0;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6].O=[CH;D2;+0:7]-[C:8]-[C;D1;H3:9]>>[C:3]-[C:2]-[N;H0;D3;+0:1](-[CH2;D2;+0:7]-[C:8]-[C;D1;H3:9])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | This compound was prepared in a similar fashion as that described in Example 84 from Compound 192 (Structure 33 of Scheme VI, where R1═H, n=1) and propionaldehyde. 1H NMR (400 MHz, CDCl3) 11.23 (br. s, 1H), 7.07 (s, 1H), 6.99 (s, 1H), 6.78 (s, 1H), 3.34 (t, 2H, J=5.6), 3.26 (t, 2H, J=7.4), 2.88 (t, 2H, J=6.3), 1.97 (m,... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aldehyde.Tertiary amine | Tertiary amine | c1ccc2cc3c(cc2n1)CCCN3 | c1ccc2cc3c(cc2n1)CCCN3 | c1ccc2cc3c(cc2n1)CCCN3 | HF | null | null | null | CCC=O.O=c1cc(C(F)(F)F)c2cc3c(cc2[nH]1)CCCN3CC(F)(F)F>>CCCN1CCCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7a53433ac6064883800fb9189592d274 | CCCN1CCCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc21>>CCN1CCCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc21 | FC(C1=CC(NC2=CC=3CCCN(C3C=C21)CCC)=O)(F)F.C(C)=O>>FC(C1=CC(NC2=CC=3CCCN(C3C=C21)CC)=O)(F)F | C[CH2:1][CH2:2][N:3]1[CH2:4][CH2:5][CH2:6][c:7]2[cH:8][c:9]3[nH:10][c:11](=[O:12])[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[c:19]3[cH:20][c:21]21>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][CH2:6][c:7]2[cH:8][c:9]3[nH:10][c:11](=[O:12])[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[c:19]3[cH:20][c:21]21 | CCCN1CCCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc21 | CCN1CCCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc21 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=c1ccc2cc3c(cc2[nH]1)CCCN3 | C-[CH2;D2;+0:1]-[C:2]-[#7:3]>>[#7:3]-[C:2]-[CH3;D1;+0:1] | null | [] | null | null | null | null | This compound was prepared in a similar fashion as that described in Example 84 from Compound 192 (Structure 33 of Scheme VI, where R1═H, n=1) and acetaldehyde. 1H NMR (400 MHz, CDCl3) 11.23 (br. s, 1H), 7.07 (s, 1H), 7.00 (s, 1H), 6.82 (s, 1H), 3.39 (q, 2H, J=7.1), 3.31 (t, 2H, J=5.6), 2.88 (t, 2H, J=6.4), 1.98 (m, 2H... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2cc3c(cc2n1)CCCN3 | Other | null | null | null | CCCN1CCCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc21>>CCN1CCCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc21 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1bab2121c57e480fb6fea7acf1aeed55 | CCN1CCCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc21.O=CC1CC1>>O=c1cc(C(F)(F)F)c2cc3c(cc2[nH]1)CCCN3CC1CC1 | FC(C1=CC(NC2=CC=3CCCN(C3C=C21)CC)=O)(F)F.C1(CC1)C=O>>FC(C1=CC(NC2=CC=3CCCN(C3C=C21)CC2CC2)=O)(F)F | CC[N:19]1[c:11]2[cH:10][c:9]3[c:4]([C:5]([F:6])([F:7])[F:8])[cH:3][c:2](=[O:1])[nH:15][c:14]3[cH:13][c:12]2[CH2:16][CH2:17][CH2:18]1.O=[CH:20][CH:21]1[CH2:22][CH2:23]1>>[O:1]=[c:2]1[cH:3][c:4]([C:5]([F:6])([F:7])[F:8])[c:9]2[cH:10][c:11]3[c:12]([cH:13][c:14]2[nH:15]1)[CH2:16][CH2:17][CH2:18][N:19]3[CH2:20][CH:21]1[CH2:... | CCN1CCCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc21.O=CC1CC1 | O=c1cc(C(F)(F)F)c2cc3c(cc2[nH]1)CCCN3CC1CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a039c447a43237c5c9d86b962761feb82e1bd4fbab0200a690d8ab9cdf0176f5 | 2db92e8910de3b0427c118b680e1a0a612a1520e71fb0f87110d867c18814b86 | O=c1ccc2cc3c(cc2[nH]1)CCCN3CC1CC1 | C-C-[N;H0;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6].O=[CH;D2;+0:7]-[C:8]1-[C:9]-[C:10]-1>>[C:3]-[C:2]-[N;H0;D3;+0:1](-[CH2;D2;+0:7]-[C:8]1-[C:9]-[C:10]-1)-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | This compound was prepared in a similar fashion as that described in Example 84 from Compound 192 (Structure 33 of Scheme VI, where R1═H, n=1) and cyclopropanecarboxaldehyde. 1H NMR (400 MHz, CDCl3) 11.44 (br. s, 1H), 7.06 (s, 1H), 7.00 (s, 1H), 6.92 (s, 1H), 3.40 (t, 2H, J=5.6), 3.21 (d, 2H, J=6.2), 2.90 (t, 2H, J=6.3... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Tertiary amine | Tertiary amine | c1ccc2cc3c(cc2n1)CCCN3 | c1ccc2cc3c(cc2n1)CCCN3 | c1ccc2cc3c(cc2n1)CCCN3.C1CC1 | HO- | null | null | null | CCN1CCCc2cc3[nH]c(=O)cc(C(F)(F)F)c3cc21.O=CC1CC1>>O=c1cc(C(F)(F)F)c2cc3c(cc2[nH]1)CCCN3CC1CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-01936e41f7b8411097cac0ece127d939 | C1CCOC1.CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)O.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.On1nnc2ccccc21>>CC(C)C[C@@H](NC(=O)[C@@H](Cc1ccccc1)NC(=O)OC(C)(C)C)C(=O)OCc1ccccc1 | CCN=C=NCCCN(C)C.N([C@H](CC1=CC=CC=C1)C(=O)O)C(=O)OC(C)(C)C.C1=CC=C2C(=C1)N=NN2O.O.CCN(C(C)C)C(C)C.C1CCOC1>>N([C@H](CC1=CC=CC=C1)C(=O)N[C@H](CC(C)C)C(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C | O1[CH2:31][CH2:30][CH2:29][CH2:34]1.[C@H:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[C:25](=[O:26])[OH:27].CC(C)N([CH:2](C)C)[CH2:28]C.CCN=[C:7]=[N:6][CH2:5]C[CH2:4]N([CH3:1])[CH3:3].c1c[cH:32][cH:33]c2c1nnn2[OH:8]>>[CH3:1][CH:2]([CH3:3])[CH2:4... | C1CCOC1.CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)O.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.On1nnc2ccccc21 | CC(C)C[C@@H](NC(=O)[C@@H](Cc1ccccc1)NC(=O)OC(C)(C)C)C(=O)OCc1ccccc1 | null | null | null | Acylation | OtherReaction | 3cc15fe545c55343313ca2ed99c5d01090584000858b7b955125c18f51f57e56 | bc8c034adb1d0ae860e65346523248e4908aabaf55689f1a91c05858dc8db84e | O=C(CCc1ccccc1)NCC(=O)OCc1ccccc1 | C-C-N=[C;H0;D2;+0:1]=[N;H0;D2;+0:2]-[CH2;D2;+0:3]-C-[CH2;D2;+0:4]-N(-[CH3;D1;+0:5])-[CH3;D1;+0:6].C-[CH2;D2;+0:7]-N(-C(-C)-C)-[CH;D3;+0:8](-C)-C.O1-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[CH2;D2;+0:12]-1.[C;D1;H3:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[#8:17]-[C:18](=[O;D1;H0:19])-[#7:20]-[C@H;D3;+0:21](-[C:22]-... | 88 | [{"value": 88.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | These syntheses were carried out according to the scheme shown in FIG. 4. The intermediates described below correspond to those shown in FIG. 4. To a suspension of Boc-D-Phe-OH intermediate I-1 (7.96 g, 30.0 mmol), D-Leu-OBn p-TsOH intermediate 1-2 (11.80 g, 30.0 mmol), HOBt monohydrate (4.46 g, 33.0 mmol) and DIEA (8.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Tertiary amine.Tertiary amine | Ester.Secondary amide | C1CCOC1.c1ccc2[nH]nnc2c1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | null | null | 8 | C1CCOC1.CC(C)(C)OC(=O)N[C@H](Cc1ccccc1)C(=O)O.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.On1nnc2ccccc21>>CC(C)C[C@@H](NC(=O)[C@@H](Cc1ccccc1)NC(=O)OC(C)(C)C)C(=O)OCc1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f8ba92078b904485847e2987af2a83d5 | CC(C)C[C@@H](NC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@@H](Cc1ccccc1)NC(=O)OC(C)(C)C)C(=O)OCc1ccccc1>>CC(C)C[C@@H](NC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@@H](Cc1ccccc1)NC(=O)OC(C)(C)C)C(=O)O | N([C@H](CC1=CC=CC=C1)C(=O)N[C@H](CC1=CC=CC=C1)C(=O)N[C@H](CC(C)C)C(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C>>N([C@H](CC1=CC=CC=C1)C(=O)N[C@H](CC1=CC=CC=C1)C(=O)N[C@H](CC(C)C)C(=O)O)C(=O)OC(C)(C)C | c1ccc(C[O:38][C:36]([C@@H:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[NH:6][C:7](=[O:8])[C@@H:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[NH:17][C:18](=[O:19])[C@@H:20]([CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[NH:28][C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:37])cc1>>[CH3:1][CH:2]([CH3:3]... | CC(C)C[C@@H](NC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@@H](Cc1ccccc1)NC(=O)OC(C)(C)C)C(=O)OCc1ccccc1 | CC(C)C[C@@H](NC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@@H](Cc1ccccc1)NC(=O)OC(C)(C)C)C(=O)O | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(CCc1ccccc1)NCCc1ccccc1 | [C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4] | null | [] | null | null | 8 | HOUR | In a flask flushed with nitrogen was added wet palladium on carbon (1.8 g) and a solution of Boc-D-Phe-D-Phe-D-Leu-OBn, intermediate 1-5 (11.1 g, 18.05 mmol) in methanol (50 μL). The mixture was stirred under a hydrogen balloon overnight. After filtration through celite, methanol was evaporated under reduced pressure. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | CO | null | 8 | CC(C)C[C@@H](NC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@@H](Cc1ccccc1)NC(=O)OC(C)(C)C)C(=O)OCc1ccccc1>CO>CC(C)C[C@@H](NC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@@H](Cc1ccccc1)NC(=O)OC(C)(C)C)C(=O)O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5891a95dbe0a4f5487ba99d0197a9015 | CCNC.Cc1cc(Oc2ccnc(N(C)c3ccccc3)n2)c(C)cc1N>>CCN(C)C=Nc1cc(C)c(Oc2ccnc(N(C)c3ccccc3)n2)cc1C | CNCC.NC1=CC(=C(OC2=NC(=NC=C2)N(C2=CC=CC=C2)C)C=C1C)C.COC(OC)OC.C1(=CC=C(C=C1)S(=O)(=O)O)C>>CC1=C(C=C(C(=C1)OC1=NC(=NC=C1)N(C1=CC=CC=C1)C)C)N=CN(C)CC | [CH3:1][CH2:2][NH:3][CH3:4].[NH2:6][c:7]1[cH:8][c:9]([CH3:10])[c:11]([O:12][c:13]2[cH:14][cH:15][n:16][c:17]([N:18]([CH3:19])[c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[n:26]2)[cH:27][c:28]1[CH3:29]>>[CH3:1][CH2:2][N:3]([CH3:4])[CH:5]=[N:6][c:7]1[cH:8][c:9]([CH3:10])[c:11]([O:12][c:13]2[cH:14][cH:15][n:16][c:17]([N:18... | CCNC.Cc1cc(Oc2ccnc(N(C)c3ccccc3)n2)c(C)cc1N | CCN(C)C=Nc1cc(C)c(Oc2ccnc(N(C)c3ccccc3)n2)cc1C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | fd5f18480460ffdcbb2cf67fb9a0ea027840d003b59d0f03e938676e8411277a | 94c1b22fc7ef4896e756a626b2579f8a24dd783d1ddcea171ef614b8292096fe | c1ccc(Nc2nccc(Oc3ccccc3)n2)cc1 | [C;D1;H3:1]-[C:2]-[NH;D2;+0:3]-[C;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:1]-[C:2]-[N;H0;D3;+0:3](-[C;D1;H3:4])-[C:9]=[N;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 18 | HOUR | To a mixture of 252 mg (0.7 mmol) of [4-(4-Amino-2,5-dimethyl-phenoxy)-pyrimidin-2-yl]-methyl-phenyl-amine and 4 ml of trimethoxymethane, 20 mg of p-toluene sulfonic acid were added. The reaction mixture was refluxed for 2 hrs and concentrated in vacuo. The mixture was solved in 10 ml of dichloromethane and 62 mg (1.05... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | Other | null | null | 18 | CCNC.Cc1cc(Oc2ccnc(N(C)c3ccccc3)n2)c(C)cc1N>>CCN(C)C=Nc1cc(C)c(Oc2ccnc(N(C)c3ccccc3)n2)cc1C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-610324e3dbed44829fe73fecbe0634b1 | Cc1cc(O)c(C)cc1N.Clc1ccnc(Cl)n1>>Cc1cc(Oc2ccnc(Cl)n2)c(C)cc1N | NC1=CC(=C(C=C1C)O)C.[OH-].[Na+].ClC1=NC=CC(=N1)Cl>>ClC1=NC=CC(=N1)OC1=CC(=C(C=C1C)N)C | [CH3:1][c:2]1[cH:3][c:4]([OH:5])[c:13]([CH3:14])[cH:15][c:16]1[NH2:17].Cl[c:6]1[cH:7][cH:8][n:9][c:10]([Cl:11])[n:12]1>>[CH3:1][c:2]1[cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][n:9][c:10]([Cl:11])[n:12]2)[c:13]([CH3:14])[cH:15][c:16]1[NH2:17] | Cc1cc(O)c(C)cc1N.Clc1ccnc(Cl)n1 | Cc1cc(Oc2ccnc(Cl)n2)c(C)cc1N | null | null | CC(=O)C.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 38da1e480b17968341fc50d07104da93d31f20765e3b36e5a0790cb6b1d88a10 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1.[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[Cl;D1;H0:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]):[c:7]:[c:6]:[#7;a:5]:1 | null | [] | null | null | 20 | HOUR | A solution of 7.55 g (55 mmol) 4-amino-2,5-dimethylphenol and 2.4 g NaOH (2M) in 30 ml water were added dropwise to a solution of 7.45 g (50.0 mmol) of 2,4-dichloropyrimidine in 50 ml of acetone. The reaction mixture was stirred for 20 h at ambient temperature. After concentration in vacuo and addition of 150 ml water ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1 | HCl | CC(=O)C.O | null | 20 | Cc1cc(O)c(C)cc1N.Clc1ccnc(Cl)n1>CC(=O)C.O>Cc1cc(Oc2ccnc(Cl)n2)c(C)cc1N |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-cc6e2af832e647b48d62bc7d748f45c5 | CNc1ccccc1.Cc1cc(Oc2ccnc(Cl)n2)c(C)cc1N>>Cc1cc(Oc2ccnc(N(C)c3ccccc3)n2)c(C)cc1N | ClC1=NC=CC(=N1)OC1=CC(=C(C=C1C)N)C.CNC1=CC=CC=C1.C(C)(=O)OCC>>NC1=CC(=C(OC2=NC(=NC=C2)N(C2=CC=CC=C2)C)C=C1C)C | [NH:11]([CH3:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.Cl[c:10]1[n:9][cH:8][cH:7][c:6]([O:5][c:4]2[cH:3][c:2]([CH3:1])[c:23]([NH2:24])[cH:22][c:20]2[CH3:21])[n:19]1>>[CH3:1][c:2]1[cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][n:9][c:10]([N:11]([CH3:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[n:19]2)[c:20]([CH3:21])[cH:... | CNc1ccccc1.Cc1cc(Oc2ccnc(Cl)n2)c(C)cc1N | Cc1cc(Oc2ccnc(N(C)c3ccccc3)n2)c(C)cc1N | null | null | Cl | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 8a13b42f4b06102b68f4963e65202071bf1d0630fbad1b11bbd8e99b9f9c8f34 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(Nc2nccc(Oc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:6]-[N;H0;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | A solution of 2.50 g (10 mmol) 4-(2-chloro-pyrimidin-4-yloxy)-2,5-dimethyl-phenylamine and 2.14 g N-methylaniline (20 mmol) in 50 ml hydrochloric acid were stirred for 20 h at 80° C. After cooling down to ambient temperature 50 ml ethyl acetate was added and the organic layer was separated. The water layer was brought ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | Cl | null | null | CNc1ccccc1.Cc1cc(Oc2ccnc(Cl)n2)c(C)cc1N>Cl>Cc1cc(Oc2ccnc(N(C)c3ccccc3)n2)c(C)cc1N |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-148cb1d56fd049cf839a5bc3d69b3e2b | CCN(C)C(OC)OC.Cc1cc(Oc2ccnc(Oc3cccc(Cl)c3C)n2)c(C)cc1N>>CCN(C)C=Nc1cc(C)c(Oc2ccnc(Oc3cccc(Cl)c3C)n2)cc1C | ClC=1C(=C(OC2=NC=CC(=N2)OC2=CC(=C(C=C2C)N)C)C=CC1)C.CO.COC(N(CC)C)OC>>ClC=1C(=C(OC2=NC=CC(=N2)OC2=CC(=C(C=C2C)N=CN(C)CC)C)C=CC1)C | CO[CH:5](OC)[N:3]([CH2:2][CH3:1])[CH3:4].[NH2:6][c:7]1[cH:8][c:9]([CH3:10])[c:11]([O:12][c:13]2[cH:14][cH:15][n:16][c:17]([O:18][c:19]3[cH:20][cH:21][cH:22][c:23]([Cl:24])[c:25]3[CH3:26])[n:27]2)[cH:28][c:29]1[CH3:30]>>[CH3:1][CH2:2][N:3]([CH3:4])[CH:5]=[N:6][c:7]1[cH:8][c:9]([CH3:10])[c:11]([O:12][c:13]2[cH:14][cH:15]... | CCN(C)C(OC)OC.Cc1cc(Oc2ccnc(Oc3cccc(Cl)c3C)n2)c(C)cc1N | CCN(C)C=Nc1cc(C)c(Oc2ccnc(Oc3cccc(Cl)c3C)n2)cc1C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0d701f00585e4f39a6a7fc9a495a6e4c12bb39eb0ddc06ef90888eddc323e4b7 | e5ad6b21478dc075562b413728aa025da8232f58653a7afd9501cb514659723b | c1ccc(Oc2ccnc(Oc3ccccc3)n2)cc1 | C-O-[CH;D3;+0:1](-O-C)-[#7:2](-[C:3])-[C;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:3]-[#7:2](-[C;D1;H3:4])-[CH;D2;+0:1]=[N;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | 45 | CELSIUS | 20 | HOUR | To a mixture of 293 mg (0.7 mmol) of 4-[2-(3-chloro-2-methyl-phenoxy)-pyrimidin-4-yloxy]-2,5-dimethyl-phenylamine in 20 ml methanol 182 mg (1.05 mmol) of N-(dimethoxymethyl)-N-methyl-ethanamine (77% pure) was added. The reaction mixture was stirred for 20 hrs at 45° C. The reaction mixture was dried over magnesium sulf... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine | null | null | null | c1ccccc1.c1cncnc1.c1ccccc1 | HO- | null | 45 | 20 | CCN(C)C(OC)OC.Cc1cc(Oc2ccnc(Oc3cccc(Cl)c3C)n2)c(C)cc1N>>CCN(C)C=Nc1cc(C)c(Oc2ccnc(Oc3cccc(Cl)c3C)n2)cc1C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-83ad101b069c418abead533afb70f9d8 | Cc1c(O)cccc1Cl.Cc1cc(Oc2ccnc(Cl)n2)c(C)cc1N>>Cc1cc(Oc2ccnc(Oc3cccc(Cl)c3C)n2)c(C)cc1N | O.ClC=1C(=C(C=CC1)O)C.[H-].[Na+].ClC1=NC=CC(=N1)OC1=CC(=C(C=C1C)N)C>>ClC=1C(=C(OC2=NC=CC(=N2)OC2=CC(=C(C=C2C)N)C)C=CC1)C | [OH:11][c:12]1[cH:13][cH:14][cH:15][c:16]([Cl:17])[c:18]1[CH3:19].Cl[c:10]1[n:9][cH:8][cH:7][c:6]([O:5][c:4]2[cH:3][c:2]([CH3:1])[c:24]([NH2:25])[cH:23][c:21]2[CH3:22])[n:20]1>>[CH3:1][c:2]1[cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][n:9][c:10]([O:11][c:12]3[cH:13][cH:14][cH:15][c:16]([Cl:17])[c:18]3[CH3:19])[n:20]2)[c:21]([CH... | Cc1c(O)cccc1Cl.Cc1cc(Oc2ccnc(Cl)n2)c(C)cc1N | Cc1cc(Oc2ccnc(Oc3cccc(Cl)c3C)n2)c(C)cc1N | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 38da1e480b17968341fc50d07104da93d31f20765e3b36e5a0790cb6b1d88a10 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccnc(Oc3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | 60 | CELSIUS | 20 | HOUR | A solution of 1.43 g (10 mmol) 3-chloro-2-methyl-phenol and 0.4 g sodium hydride (60% in paraffine, 10 mmol) in 20 ml THF were stirred for 30 min at ambient temperature. After adding 1.25 g (5 mmol) 4-(2-chloro-pyrimidin-4-yloxy)-2,5-dimethyl-phenylamine the mixture was stirred for 20 hrs at 60° C. After cooling down t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1ccccc1 | HCl | C1CCOC1 | 60 | 20 | Cc1c(O)cccc1Cl.Cc1cc(Oc2ccnc(Cl)n2)c(C)cc1N>C1CCOC1>Cc1cc(Oc2ccnc(Oc3cccc(Cl)c3C)n2)c(C)cc1N |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7ccb126b89ca40838648d5c99efc243b | CCN(C)C(OC)OC.Cc1cc(Oc2cc(C)c(N)cc2C)nc(Cl)n1>>CCN(C)C=Nc1cc(C)c(Oc2cc(C)nc(Cl)n2)cc1C | ClC1=NC(=CC(=N1)OC1=CC(=C(N)C=C1C)C)C.C(C)#N.COC(N(CC)C)OC>>ClC1=NC(=CC(=N1)OC1=CC(=C(C=C1C)N=CN(C)CC)C)C | CO[CH:5](OC)[N:3]([CH2:2][CH3:1])[CH3:4].[NH2:6][c:7]1[cH:8][c:9]([CH3:10])[c:11]([O:12][c:13]2[cH:14][c:15]([CH3:16])[n:17][c:18]([Cl:19])[n:20]2)[cH:21][c:22]1[CH3:23]>>[CH3:1][CH2:2][N:3]([CH3:4])[CH:5]=[N:6][c:7]1[cH:8][c:9]([CH3:10])[c:11]([O:12][c:13]2[cH:14][c:15]([CH3:16])[n:17][c:18]([Cl:19])[n:20]2)[cH:21][c:... | CCN(C)C(OC)OC.Cc1cc(Oc2cc(C)c(N)cc2C)nc(Cl)n1 | CCN(C)C=Nc1cc(C)c(Oc2cc(C)nc(Cl)n2)cc1C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0d701f00585e4f39a6a7fc9a495a6e4c12bb39eb0ddc06ef90888eddc323e4b7 | e5ad6b21478dc075562b413728aa025da8232f58653a7afd9501cb514659723b | c1ccc(Oc2ccncn2)cc1 | C-O-[CH;D3;+0:1](-O-C)-[#7:2](-[C:3])-[C;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:3]-[#7:2](-[C;D1;H3:4])-[CH;D2;+0:1]=[N;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | To a mixture of 310 mg (0.8 mmol) of 4-[(2-chloro-6-methylpyrimidin-4-yl)oxy]-2,5-dimethyl-aniline in 20 ml acetonitrile 208 mg (1.5 mmol) of N-(dimethoxymethyl)-N-methylethanamine (77% pure) was added. The reaction mixture was refluxed for 20 hrs. The reaction mixture was concentrated in vacuo, diluted with ethyl acet... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine | null | null | null | c1ccccc1.c1cncnc1 | HO- | null | null | null | CCN(C)C(OC)OC.Cc1cc(Oc2cc(C)c(N)cc2C)nc(Cl)n1>>CCN(C)C=Nc1cc(C)c(Oc2cc(C)nc(Cl)n2)cc1C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a317305e306944ef82b1ad5a3fc53986 | CC(C)=O.Cc1cc(O)c(C)cc1N.Clc1ccnc(Cl)n1>>Cc1cc(Oc2cc(C)c(N)cc2C)nc(Cl)n1 | NC1=CC(=C(C=C1C)O)C.[OH-].[Na+].ClC1=NC=CC(=N1)Cl.CC(=O)C>>ClC1=NC(=CC(=N1)OC1=CC(=C(N)C=C1C)C)C | CC(=O)[CH3:1].[OH:5][c:6]1[cH:7][c:8]([CH3:9])[c:10]([NH2:11])[cH:12][c:13]1[CH3:14].Cl[c:2]1[cH:3][cH:4][n:15][c:16]([Cl:17])[n:18]1>>[CH3:1][c:2]1[cH:3][c:4]([O:5][c:6]2[cH:7][c:8]([CH3:9])[c:10]([NH2:11])[cH:12][c:13]2[CH3:14])[n:15][c:16]([Cl:17])[n:18]1 | CC(C)=O.Cc1cc(O)c(C)cc1N.Clc1ccnc(Cl)n1 | Cc1cc(Oc2cc(C)c(N)cc2C)nc(Cl)n1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | a5df4cfbbc04b45d1e67e4219d1ae31ff5489ab3b6fc41ee74c5ccf007dfeffd | d663e539a886cee8ab60903f3bf6f764156cd8d57154855d3b2e42ee05e2e520 | c1ccc(Oc2ccncn2)cc1 | C-C(=O)-[CH3;D1;+0:1].Cl-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4](-[Cl;D1;H0:5]):[#7;a:6]:[cH;D2;+0:7]:[c:8]:1.[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[CH3;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4](-[Cl;D1;H0:5]):[#7;a:6]:[c;H0;D3;+0:7](-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:8]:1 | null | [] | null | null | 20 | HOUR | A solution of 4.53 g (33 mmol) 4-amino-2,5-dimethylphenol and 1.44 g NaOH (2M) in 30 ml water were added dropwise to a solution of 4.89 g (30.0 mmol) of 2,4-dichloropyrimidine in 50 ml of acetone. The reaction mixture was stirred for 20 h at ambient temperature.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Aromatic alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | O | null | 20 | CC(C)=O.Cc1cc(O)c(C)cc1N.Clc1ccnc(Cl)n1>O>Cc1cc(Oc2cc(C)c(N)cc2C)nc(Cl)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7e6296a5515441d5b10b47b9b173f03f | CCN(C)c1nc(Oc2cc(C)c([N+](=O)[O-])cc2C)ncc1Cl>>CCN(C)c1nc(Oc2cc(C)c(N)cc2C)ncc1Cl | ClC=1C(=NC(=NC1)OC1=C(C=C(C(=C1)C)[N+](=O)[O-])C)N(C)CC.CO>>NC1=CC(=C(OC2=NC=C(C(=N2)N(C)CC)Cl)C=C1C)C | O=[N+:14]([O-])[c:13]1[c:11]([CH3:12])[cH:10][c:9]([O:8][c:7]2[n:6][c:5]([N:3]([CH2:2][CH3:1])[CH3:4])[c:20]([Cl:21])[cH:19][n:18]2)[c:16]([CH3:17])[cH:15]1>>[CH3:1][CH2:2][N:3]([CH3:4])[c:5]1[n:6][c:7]([O:8][c:9]2[cH:10][c:11]([CH3:12])[c:13]([NH2:14])[cH:15][c:16]2[CH3:17])[n:18][cH:19][c:20]1[Cl:21] | CCN(C)c1nc(Oc2cc(C)c([N+](=O)[O-])cc2C)ncc1Cl | CCN(C)c1nc(Oc2cc(C)c(N)cc2C)ncc1Cl | null | null | Cl | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Oc2ncccn2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | To a solution of 8.86 g (20 mmol) 5-chloro-2-(2,5-dimethyl-4-nitrophenoxy)-N-ethyl-N-methylpyrimidin-4-amine in 50 ml hydrochloric acid and 50 ml methanol 13.5 g (60 mmol) tin-(II)-dichloro dihydrate was added and the mixture was refluxed for 4 h. After cooling down to ambient temperature the formed precipitate was fil... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1cncnc1.c1ccccc1 | Other | Cl | null | null | CCN(C)c1nc(Oc2cc(C)c([N+](=O)[O-])cc2C)ncc1Cl>Cl>CCN(C)c1nc(Oc2cc(C)c(N)cc2C)ncc1Cl |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-aa3196a16d9a4431bf69a02926667947 | CCN(C)c1nc(Cl)ncc1Cl.Cc1cc([N+](=O)[O-])c(C)cc1O>>CCN(C)c1nc(Oc2cc(C)c([N+](=O)[O-])cc2C)ncc1Cl | O.ClC1=NC=C(C(=N1)N(C)CC)Cl.[N+](=O)([O-])C1=CC(=C(C=C1C)O)C.C([O-])([O-])=O.[K+].[K+]>>ClC=1C(=NC(=NC1)OC1=C(C=C(C(=C1)C)[N+](=O)[O-])C)N(C)CC | Cl[c:7]1[n:6][c:5]([N:3]([CH2:2][CH3:1])[CH3:4])[c:22]([Cl:23])[cH:21][n:20]1.[OH:8][c:9]1[cH:10][c:11]([CH3:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17][c:18]1[CH3:19]>>[CH3:1][CH2:2][N:3]([CH3:4])[c:5]1[n:6][c:7]([O:8][c:9]2[cH:10][c:11]([CH3:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17][c:18]2[CH3:19])[n:20][cH:21][c:22]... | CCN(C)c1nc(Cl)ncc1Cl.Cc1cc([N+](=O)[O-])c(C)cc1O | CCN(C)c1nc(Oc2cc(C)c([N+](=O)[O-])cc2C)ncc1Cl | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 38da1e480b17968341fc50d07104da93d31f20765e3b36e5a0790cb6b1d88a10 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ncccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[O;H0;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | A solution of 16.8 g (40 mmol) 2,5-dichloro-N-ethyl-N-methylpyrimidin-4-amine, 7.35 g 4-nitro-2,5-dimethylphenol (44 mmol) and 8.29 g potassium carbonate (60 mmol) in 70 ml DMF were stirred for 20 hrs at 100° C. After adding the mixture to 150 ml water the resulting suspension was extracted twice with 50 ml dichloromet... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccccc1 | HCl | CN(C)C=O | null | null | CCN(C)c1nc(Cl)ncc1Cl.Cc1cc([N+](=O)[O-])c(C)cc1O>CN(C)C=O>CCN(C)c1nc(Oc2cc(C)c([N+](=O)[O-])cc2C)ncc1Cl |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6d605ae120b142b89b2218dc15bdf324 | CC(C)(N)Cc1ccc(O)cc1.O=C1COc2ccc(OCc3ccccc3)cc2N1.O=CC=O>>CC(C)(Cc1ccc(O)cc1)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 | O.C(=O)C=O.C(C1=CC=CC=C1)OC=1C=CC2=C(NC(CO2)=O)C1.CC(CC1=CC=C(C=C1)O)(C)N.Cl>>CC(CC1=CC=C(C=C1)O)(C)NCC(O)C1=CC(=CC=2NC(COC21)=O)OCC2=CC=CC=C2 | [CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1)[NH2:12].[cH:16]1[cH:17][c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][c:28]2[c:29]1[O:30][CH2:31][C:32](=[O:33])[NH:34]2.O=[CH:13][CH:14]=[O:15]>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:... | CC(C)(N)Cc1ccc(O)cc1.O=C1COc2ccc(OCc3ccccc3)cc2N1.O=CC=O | CC(C)(Cc1ccc(O)cc1)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 619c7e68b8540fa680c96d7ad8234d3c387952bfcabed4479cea2cdd18dff6e7 | d154ed7dd4f927fea6b10a1aa061ef038a280660ef05fcec85f05b5ce4f82ab4 | O=C1COc2c(CCNCCc3ccccc3)cc(OCc3ccccc3)cc2N1 | O=[CH;D2;+0:1]-[CH;D2;+0:2]=[O;H0;D1;+0:3].[C:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[NH2;D1;+0:8].[O;D1;H0:9]=[C:10]1-[#7:11]-[c:12]:[c:13](:[cH;D2;+0:14]:[c:15]:[c:16])-[#8:17]-[C:18]-1>>[C:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[NH;D2;+0:8]-[CH2;D2;+0:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:13]... | null | [] | null | null | null | null | The title compound is prepared from 10 g of (6-benzyloxy-4H-benzo[1,4]oxazin-3-one)-glyoxal hydrate and 4.6 g of 1,1-dimethyl-2-(4-hydroxyphenyl)ethylamine analogously to the method for Example 3(a). Yield: 9.0 g (64%, hydrochloride); melting point: 255° C.-258° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde.Primary amine | Secondary alcohol.Secondary amine | c1ccc2c(c1)NCCO2 | c1ccc2c(c1)NCCO2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)NCCO2 | Other | null | null | null | CC(C)(N)Cc1ccc(O)cc1.O=C1COc2ccc(OCc3ccccc3)cc2N1.O=CC=O>>CC(C)(Cc1ccc(O)cc1)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5bbcde2c94ff44219208d4f11cce28a3 | CC(C)=O.CC(C)c1ccc(CCl)cc1>>CC(C)c1ccc(CC(C)(C)O)cc1 | C(C)(C)C1=CC=C(CCl)C=C1.CC(=O)C>>C(C)(C)C1=CC=C(C=C1)CC(C)(O)C | [C:9]([CH3:10])([CH3:11])=[O:12].Cl[CH2:8][c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:14][cH:13]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][C:9]([CH3:10])([CH3:11])[OH:12])[cH:13][cH:14]1 | CC(C)=O.CC(C)c1ccc(CCl)cc1 | CC(C)c1ccc(CC(C)(C)O)cc1 | null | null | null | C-C Coupling | Grignard_alcohol | 769c01a2de8a052c306a223603a055dda0fdbaa49ef786ff9ffa9776720852e2 | afe96a58b8c6ca4e103c0c96e2a417cdee8e581054f8e646150ad555cb751905 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C;H0;D3;+0:6](-[C;D1;H3:7])=[O;H0;D1;+0:8]>>[C;D1;H3:5]-[C;H0;D4;+0:6](-[C;D1;H3:7])(-[OH;D1;+0:8])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The reaction of a Grignard compound, prepared from 20 g (119 mmol) 4-isopropylbenzyl chloride, with 11.4 mL (155 mmol) acetone yields the target compound as a colorless oil. Yield: 13.0 g (57%); mass spectrometry: [M+H]+=193.
Conditions: See reaction.notes.procedure_details.
Workup: The reaction of a Grignard compound | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Tertiary alcohol | null | null | c1ccccc1 | Other | null | null | null | CC(C)=O.CC(C)c1ccc(CCl)cc1>>CC(C)c1ccc(CC(C)(C)O)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-748a663c6d14447a9d8b0cfd2ea31882 | CC(=O)NC(C)(C)Cc1ccc(C(C)C)cc1>>CC(C)c1ccc(CC(C)(C)N)cc1 | C(C)(C)C1=CC=C(C=C1)CC(C)(C)NC(C)=O.Cl>>C(C)(C)C1=CC=C(C=C1)CC(C)(C)N | CC(=O)[NH:12][C:9]([CH2:8][c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:14][cH:13]1)([CH3:10])[CH3:11]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][C:9]([CH3:10])([CH3:11])[NH2:12])[cH:13][cH:14]1 | CC(=O)NC(C)(C)Cc1ccc(C(C)C)cc1 | CC(C)c1ccc(CC(C)(C)N)cc1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccccc1 | C-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[C;D1;H3:5]>>[C:3]-[C:2](-[C;D1;H3:4])(-[C;D1;H3:5])-[NH2;D1;+0:1] | null | [] | null | null | null | null | Reaction of 9.80 g (42 mmol) of N-[2-(4-isopropylphenyl)-1,1-dimethylethyl]acetamide analogously to the method for Example 9(c). Yield: 7.00 g (71%, hydrochloride); melting point 202° C.-206° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1 | HO- | null | null | null | CC(=O)NC(C)(C)Cc1ccc(C(C)C)cc1>>CC(C)c1ccc(CC(C)(C)N)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f142153d51594f39b957e0c4213d6559 | CC(C)c1ccc(CC(C)(C)N)cc1.CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2>>CC(C)c1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1 | N.[BH4-].[Na+].Cl.C(C1=CC=CC=C1)OC1OC2=C(NC1=O)C=CC=C2C(C(O)OCC)=O.C(C)(C)C1=CC=C(C=C1)CC(C)(C)N>>C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=CC=C(C=C1)C(C)C)(C)C)O | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][C:9]([CH3:10])([CH3:11])[NH2:12])[cH:35][cH:36]1.CCO[CH:13](O)[C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:27][c:28]2[c:29]1[O:30][CH:31]([O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[C:32](=[O:33])[NH:34]2>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH2... | CC(C)c1ccc(CC(C)(C)N)cc1.CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2 | CC(C)c1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1 | null | null | C(C)(=O)OCC.CC(=O)C.O.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | e4b89399a4f55a0af960a37042cea8a8c75c6298d132f9a4be2364ae88492a84 | 4ef679604d0e977a363fff66519675c20f55f1d944c6c8949280ef4bc8f85467 | O=C1COc2c(CCNCCc3ccccc3)cc(OCc3ccccc3)cc2N1 | C-C-O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]1:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]2:[c:9]:1-[#8:10]-[CH;D3;+0:11](-[O;H0;D2;+0:12]-[C:13]-[c:14])-[C:15](=[O;D1;H0:16])-[#7:17]-2.[C:18]-[C:19](-[C;D1;H3:20])(-[C;D1;H3:21])-[NH2;D1;+0:22]>>[C:18]-[C:19](-[C;D1;H3:20])(-[C;D1;H3:21])-[NH;D2;+0:22]-[CH2;D2;+0:1]-... | null | [] | null | null | 1 | HOUR | 2.18 g (6.1 mmol) of benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 1.1 g (5.8 mmol) of 2-(4-isopropylphenyl)-1,1-dimethylethylamine are stirred in 40 mL ethanol at 50° C.-80° C. for one hour. After cooling to ambient temperature, 0.24 g (6.3 mmol) sodium borohydride is added. The mixture is stirr... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Ether.Secondary alcohol.Primary amine | Ether.Ether.Secondary alcohol.Secondary amine | c1ccc2c(c1)NCCO2 | c1ccc2c(c1)NCCO2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)NCCO2 | HO- | C(C)(=O)OCC.CC(=O)C.O.C(C)O | null | 1 | CC(C)c1ccc(CC(C)(C)N)cc1.CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2>C(C)(=O)OCC.CC(=O)C.O.C(C)O>CC(C)c1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7e398e689be1483499840935a90256d4 | CC(C)c1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1>>CC(C)c1ccc(CC(C)(C)NCC(O)c2cc(O)cc3c2OCC(=O)N3)cc1 | C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=CC=C(C=C1)C(C)C)(C)C)O>>OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=CC=C(C=C1)C(C)C)(C)C)O | c1ccc(C[O:19][c:18]2[cH:17][c:16]([CH:14]([CH2:13][NH:12][C:9]([CH2:8][c:7]3[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:29][cH:28]3)([CH3:10])[CH3:11])[OH:15])[c:22]3[c:21]([cH:20]2)[NH:27][C:25](=[O:26])[CH2:24][O:23]3)cc1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][C:9]([CH3:10])([CH3:11])[NH:12][CH2:13][... | CC(C)c1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1 | CC(C)c1ccc(CC(C)(C)NCC(O)c2cc(O)cc3c2OCC(=O)N3)cc1 | null | [Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1COc2c(CCNCCc3ccccc3)cccc2N1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | null | null | 1.6 g (3.0 mmol) of 6-benzyloxy-8-{1-hydroxy-2-[2-(4-isopropylphenyl)-1,1-dimethylethylamino]ethyl}-4H-benzo[1,4]oxazin-3-one is dissolved in methanol and hydrogenated with palladium on charcoal as catalyst at normal pressure and ambient temperature. The catalyst is suction filtered, the solvent distilled off, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)NCCO2 | Other | [Pd].CO | null | null | CC(C)c1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1>[Pd].CO>CC(C)c1ccc(CC(C)(C)NCC(O)c2cc(O)cc3c2OCC(=O)N3)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8627ea437cdb47b29433fbbf7c6e18c6 | CCc1ccc(CC(C)=O)cc1>>CCc1ccc(CC(C)(C)O)cc1 | [Cl-].[NH4+].C[Mg]Br.C(C)C1=CC=C(C=C1)CC(C)=O>>C(C)C1=CC=C(C=C1)CC(C)(O)C | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8]([CH3:10])=[O:11])[cH:12][cH:13]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8]([CH3:9])([CH3:10])[OH:11])[cH:12][cH:13]1 | CCc1ccc(CC(C)=O)cc1 | CCc1ccc(CC(C)(C)O)cc1 | null | null | C(C)OCC | Miscellaneous | OtherReaction | 7e61014f084ef66fe8691c8f1abaf493e11079effe9d87ae329e041d937b8b3a | 8811b4d793f7cfa9f0f1f47a008648edabb54f371f76dfa680dd5b2e1564c6c5 | c1ccccc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[C:4]-[c:5]>>[C;D1;H3:1]-[C;H0;D4;+0:2](-[C;D1;H3:6])(-[OH;D1;+0:3])-[C:4]-[c:5] | null | [] | null | null | null | null | 14.8 g (90 mmol) of 1-(4-ethylphenyl)propan-2-one dissolved in diethyl ether is added dropwise to 39 mL of a 3 molar solution of methylmagnesium bromide in diethyl ether while being cooled with an ice bath in such a way that the temperature does not exceed 30° C. After the addition has ended, the reaction mixture is re... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | null | null | c1ccccc1 | Other | C(C)OCC | null | null | CCc1ccc(CC(C)=O)cc1>C(C)OCC>CCc1ccc(CC(C)(C)O)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c2a674e1238f4dc8b04cc0d29f019f60 | CC#N.CCc1ccc(CC(C)(C)O)cc1.O=S(=O)(O)O>>CCc1ccc(CC(C)(C)NC(C)=O)cc1 | [OH-].[Na+].S(O)(O)(=O)=O.C(C)C1=CC=C(C=C1)CC(C)(O)C.C(C)#N>>C(C)C1=CC=C(C=C1)CC(C)(C)NC(C)=O | [N:11]#[C:12][CH3:13].O[C:8]([CH2:7][c:6]1[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:16][cH:15]1)([CH3:9])[CH3:10].O=S(=O)(O)[OH:14]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8]([CH3:9])([CH3:10])[NH:11][C:12]([CH3:13])=[O:14])[cH:15][cH:16]1 | CC#N.CCc1ccc(CC(C)(C)O)cc1.O=S(=O)(O)O | CCc1ccc(CC(C)(C)NC(C)=O)cc1 | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | 1d5b8ab7abc796c8fe1a4bbe88d643f3667784ffa1e5d5bdf2ecec75239c4174 | 351ef33c26e45ccdbae92f97c6925d748e3ebc471a863d8f431e8ded2d7e850d | c1ccccc1 | O-S(=O)(=O)-[OH;D1;+0:1].O-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[C:5]-[c:6].[C;D1;H3:7]-[C;H0;D2;+0:8]#[N;H0;D1;+0:9]>>[C;D1;H3:3]-[C;H0;D4;+0:2](-[C;D1;H3:4])(-[C:5]-[c:6])-[NH;D2;+0:9]-[C;H0;D3;+0:8](-[C;D1;H3:7])=[O;H0;D1;+0:1] | null | [] | null | null | 1 | HOUR | 6.2 mL of concentrated sulfuric acid is added dropwise to 15.5 g (87 mmol) of 1-(4-ethylphenyl)-2-methylpropan-2-ol in 4.8 mL (91 mmol) acetonitrile and 15 mL glacial acetic acid within 15 minutes, during which time the temperature rises to 65° C. It is then stirred for one hour, diluted with ice water, and made alkali... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Tertiary alcohol | Secondary amide | null | null | c1ccccc1 | HO- | C(C)(=O)O | null | 1 | CC#N.CCc1ccc(CC(C)(C)O)cc1.O=S(=O)(O)O>C(C)(=O)O>CCc1ccc(CC(C)(C)NC(C)=O)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d40536500a4f4ac6b14cb0966f32001e | CCc1ccc(CC(C)(C)NC(C)=O)cc1>>CCc1ccc(CC(C)(C)N)cc1 | C(C)C1=CC=C(C=C1)CC(C)(C)NC(C)=O.[OH-].[K+].Cl.C(C)OCC>>C(C)C1=CC=C(C=C1)CC(C)(C)N | CC(=O)[NH:11][C:8]([CH2:7][c:6]1[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:13][cH:12]1)([CH3:9])[CH3:10]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8]([CH3:9])([CH3:10])[NH2:11])[cH:12][cH:13]1 | CCc1ccc(CC(C)(C)NC(C)=O)cc1 | CCc1ccc(CC(C)(C)N)cc1 | null | null | C(CO)O.C(C)#N | Reduction | Hydrogenolysis of amides/imides/carbamates | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccccc1 | C-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[C;D1;H3:5]>>[C:3]-[C:2](-[C;D1;H3:4])(-[C;D1;H3:5])-[NH2;D1;+0:1] | null | [] | null | null | null | null | 16.3 g (74 mmol) of N-[2-(4-ethylphenyl)-1,1-dimethylethyl]acetamide and 8.0 g of potassium hydroxide are refluxed for 15 hours in 60 mL ethylene glycol. The reaction mixture is combined with ice water and extracted three times with diethyl ether. The combined organic phases are washed with water, dried with sodium sul... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1 | HO- | C(CO)O.C(C)#N | null | null | CCc1ccc(CC(C)(C)NC(C)=O)cc1>C(CO)O.C(C)#N>CCc1ccc(CC(C)(C)N)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a2344d268bf746db834448ce1d1b93c9 | CCOC(O)C(=O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2.CCc1ccc(CC(C)(C)N)cc1>>CCc1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1 | C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(C(O)OCC)=O.C(C)C1=CC=C(C=C1)CC(C)(C)N.Cl>>C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=CC=C(C=C1)CC)(C)C)O | CCO[CH:12](O)[C:13](=[O:14])[c:15]1[cH:16][c:17]([O:18][CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[cH:26][c:27]2[c:28]1[O:29][CH2:30][C:31](=[O:32])[NH:33]2.[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8]([CH3:9])([CH3:10])[NH2:11])[cH:34][cH:35]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8]([CH3:9])... | CCOC(O)C(=O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2.CCc1ccc(CC(C)(C)N)cc1 | CCc1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1fdebd18d8e186352a5054d1639a246066c291a759c2941bdb27defc05ab0b96 | 270f718637e505454980bf4a24a04f3a3a166f4d4160855797b4e1923ac25b66 | O=C1COc2c(CCNCCc3ccccc3)cc(OCc3ccccc3)cc2N1 | C-C-O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6]-[#8:7].[C:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[NH2;D1;+0:12]>>[#8:7]-[c:6]:[c:4](-[CH;D3;+0:2](-[OH;D1;+0:3])-[CH2;D2;+0:1]-[NH;D2;+0:12]-[C:9](-[C:8])(-[C;D1;H3:10])-[C;D1;H3:11]):[c:5] | null | [] | null | null | null | null | The target compound is prepared analogously to the method for Example 8(d) from 2.14 g (6.0 mmol) of 6-benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 1.0 g (5.6 mmol) of 2-(4-ethylphenyl)-1,1-dimethylethylamine. White solid. Yield: 1.7 g (54%, hydrochloride); melting point 210° C.-214° C.
Conditio... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Secondary alcohol.Primary amine | Secondary alcohol.Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)NCCO2 | HO- | null | null | null | CCOC(O)C(=O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2.CCc1ccc(CC(C)(C)N)cc1>>CCc1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a077ae3605094eb692cd00682fc03c6f | CC(C)=Cc1ccc(F)c(C)c1.O=S(=O)(O)O.[C-]#N>>Cc1cc(CC(C)(C)NC=O)ccc1F | [OH-].[Na+].S(O)(O)(=O)=O.[C-]#N.[Na+].FC1=C(C=C(C=C1)C=C(C)C)C>>FC1=C(C=C(C=C1)CC(C)(C)NC=O)C | [CH3:1][c:2]1[cH:3][c:4]([CH:5]=[C:6]([CH3:7])[CH3:8])[cH:12][cH:13][c:14]1[F:15].O=S(=O)(O)[OH:11].[N:9]#[C-:10]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][C:6]([CH3:7])([CH3:8])[NH:9][CH:10]=[O:11])[cH:12][cH:13][c:14]1[F:15] | CC(C)=Cc1ccc(F)c(C)c1.O=S(=O)(O)O.[C-]#N | Cc1cc(CC(C)(C)NC=O)ccc1F | null | null | C(C)(=O)O | Heteroatom Alkylation and Arylation | OtherReaction | a981f34c69e52391b77f7c941ccdb6ca0c3afd7148475c206b7953c81091b4a4 | 2ea4f633e477f6ccb356ebb42e8b8735f5a544f09735b4353e71b0e0474d153c | c1ccccc1 | O-S(=O)(=O)-[OH;D1;+0:1].[C-;H0;D1:2]#[N;H0;D1;+0:3].[C;D1;H3:4]-[C;H0;D3;+0:5](-[C;D1;H3:6])=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:4]-[C;H0;D4;+0:5](-[C;D1;H3:6])(-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10])-[NH;D2;+0:3]-[CH;D2;+0:2]=[O;H0;D1;+0:1] | null | [] | null | null | 1 | HOUR | 4.9 mL concentrated sulfuric acid are added dropwise at 5° C.-15° C. to 1.5 g (31 mmol) sodium cyanide in 5 mL glacial acetic acid. Then the mixture is combined with 3.9 g (24 mmol) of 1-fluoro-2-methyl-4-(2-methylpropenyl)benzene, dissolved in 10 mL glacial acetic acid, and stirred for 1 hour at 50° C.-60° C. The reac... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amide | null | null | c1ccccc1 | Other | C(C)(=O)O | null | 1 | CC(C)=Cc1ccc(F)c(C)c1.O=S(=O)(O)O.[C-]#N>C(C)(=O)O>Cc1cc(CC(C)(C)NC=O)ccc1F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4ed08f9c2c624361bf82204397ccf5ba | CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2.Cc1cc(CC(C)(C)N)ccc1F>>Cc1cc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)ccc1F | C(C1=CC=CC=C1)OC1OC2=C(NC1=O)C=CC=C2C(C(O)OCC)=O.FC1=C(C=C(C=C1)CC(C)(C)N)C.Cl>>C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=CC(=C(C=C1)F)C)(C)C)O | CCO[CH:10](O)[C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:24][c:25]2[c:26]1[O:27][CH:28]([O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[C:29](=[O:30])[NH:31]2.[CH3:1][c:2]1[cH:3][c:4]([CH2:5][C:6]([CH3:7])([CH3:8])[NH2:9])[cH:32][cH:33][c:34]1[F:35]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][C:6]([CH3:7])([CH3:8])[NH:9][... | CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2.Cc1cc(CC(C)(C)N)ccc1F | Cc1cc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)ccc1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e4b89399a4f55a0af960a37042cea8a8c75c6298d132f9a4be2364ae88492a84 | 4ef679604d0e977a363fff66519675c20f55f1d944c6c8949280ef4bc8f85467 | O=C1COc2c(CCNCCc3ccccc3)cc(OCc3ccccc3)cc2N1 | C-C-O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]1:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]2:[c:9]:1-[#8:10]-[CH;D3;+0:11](-[O;H0;D2;+0:12]-[C:13]-[c:14])-[C:15](=[O;D1;H0:16])-[#7:17]-2.[C:18]-[C:19](-[C;D1;H3:20])(-[C;D1;H3:21])-[NH2;D1;+0:22]>>[C:18]-[C:19](-[C;D1;H3:20])(-[C;D1;H3:21])-[NH;D2;+0:22]-[CH2;D2;+0:1]-... | null | [] | null | null | null | null | 1.10 g (3.1 mmol) of benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 0.50 g (2.8 mmol) of 2-(4-fluoro-3-methylphenyl)-1,1-dimethylethylamine are reacted and worked up analogously to the method for Example 8(d). White solid. Yield: 0.75 g (47%, hydrochloride); melting point 228° C.-230° C.
Condition... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Ether.Secondary alcohol.Primary amine | Ether.Ether.Secondary alcohol.Secondary amine | c1ccc2c(c1)NCCO2 | c1ccc2c(c1)NCCO2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)NCCO2 | HO- | null | null | null | CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2.Cc1cc(CC(C)(C)N)ccc1F>>Cc1cc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)ccc1F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2f2ca50b285c466c8332057972630786 | Cc1cc(F)ccc1CC(C)(C)NC=O>>Cc1cc(F)ccc1CC(C)(C)N | FC1=CC(=C(C=C1)CC(C)(C)NC=O)C.Cl>>FC1=CC(=C(C=C1)CC(C)(C)N)C | O=C[NH:13][C:10]([CH2:9][c:8]1[c:2]([CH3:1])[cH:3][c:4]([F:5])[cH:6][cH:7]1)([CH3:11])[CH3:12]>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][c:8]1[CH2:9][C:10]([CH3:11])([CH3:12])[NH2:13] | Cc1cc(F)ccc1CC(C)(C)NC=O | Cc1cc(F)ccc1CC(C)(C)N | null | null | null | Reduction | Reduction of primary amides to amines | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccccc1 | O=C-[NH;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[C;D1;H3:5]>>[C:3]-[C:2](-[C;D1;H3:4])(-[C;D1;H3:5])-[NH2;D1;+0:1] | null | [] | null | null | null | null | In order to prepare the amine, 27.0 g (130 mmol) of N-[2-(4-fluoro-2-methylphenyl)-1,1-dimethylethyl]formamide is reacted as described in the method for Example 10(c). White solid. Yield: 15.5 g (55%, hydrochloride); melting point: 277° C.-280° C.
Conditions: See reaction.notes.procedure_details.
Workup: is reacted | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1 | Other | null | null | null | Cc1cc(F)ccc1CC(C)(C)NC=O>>Cc1cc(F)ccc1CC(C)(C)N |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f053f0ee2a084b4fb3d6510862a29e13 | CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2.Cc1cc(F)ccc1CC(C)(C)N>>Cc1cc(F)ccc1CC(C)(C)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 | C(C1=CC=CC=C1)OC1OC2=C(NC1=O)C=CC=C2C(C(O)OCC)=O.FC1=CC(=C(C=C1)CC(C)(C)N)C.Cl>>C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=C(C=C(C=C1)F)C)(C)C)O | CCO[CH:14](O)[C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:28][c:29]2[c:30]1[O:31][CH:32]([O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[C:33](=[O:34])[NH:35]2.[CH3:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][c:8]1[CH2:9][C:10]([CH3:11])([CH3:12])[NH2:13]>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][c:8]1[CH2:9][C:10]... | CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2.Cc1cc(F)ccc1CC(C)(C)N | Cc1cc(F)ccc1CC(C)(C)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e4b89399a4f55a0af960a37042cea8a8c75c6298d132f9a4be2364ae88492a84 | 4ef679604d0e977a363fff66519675c20f55f1d944c6c8949280ef4bc8f85467 | O=C1COc2c(CCNCCc3ccccc3)cc(OCc3ccccc3)cc2N1 | C-C-O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]1:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]2:[c:9]:1-[#8:10]-[CH;D3;+0:11](-[O;H0;D2;+0:12]-[C:13]-[c:14])-[C:15](=[O;D1;H0:16])-[#7:17]-2.[C:18]-[C:19](-[C;D1;H3:20])(-[C;D1;H3:21])-[NH2;D1;+0:22]>>[C:18]-[C:19](-[C;D1;H3:20])(-[C;D1;H3:21])-[NH;D2;+0:22]-[CH2;D2;+0:1]-... | null | [] | null | null | null | null | Prepared analogously to the method for Example 8(d) from 0.95 g (2.66 mmol) of benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 0.43 g (2.37 mmol) of 2-(4-fluoro-2-methylphenyl)-1,1-dimethylethylamine. Yield: 0.75 g (55%, hydrochloride); melting point 233° C.-236° C.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Ether.Secondary alcohol.Primary amine | Ether.Ether.Secondary alcohol.Secondary amine | c1ccc2c(c1)NCCO2 | c1ccc2c(c1)NCCO2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)NCCO2 | HO- | null | null | null | CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2.Cc1cc(F)ccc1CC(C)(C)N>>Cc1cc(F)ccc1CC(C)(C)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-09a95e78dab74866bdc4b0f4e523c6ac | CC(C)=O.Fc1ccc([CH2][Mg][Br])c(F)c1>>CC(C)(O)Cc1ccc(F)cc1F | CC(=O)C.FC1=C(C[Mg]Br)C=CC(=C1)F.[Cl-].[NH4+]>>FC1=C(C=CC(=C1)F)CC(C)(O)C | [CH3:1][C:2]([CH3:3])=[O:4].[Br][Mg][CH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]1[F:13]>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]1[F:13] | CC(C)=O.Fc1ccc([CH2][Mg][Br])c(F)c1 | CC(C)(O)Cc1ccc(F)cc1F | null | null | C(C)OCC | C-C Coupling | Grignard from ketone to alcohol | 4737491c367e985251b8e6236de937de0f5f777bcb09b5971359565d81ed217a | 5854166cd4ea706bc07d74dc79eb8f4a990bc6c5eacbf0ca947d88ee86e78fdf | c1ccccc1 | [Br]-[Mg]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C;H0;D3;+0:6](-[C;D1;H3:7])=[O;H0;D1;+0:8]>>[C;D1;H3:5]-[C;H0;D4;+0:6](-[C;D1;H3:7])(-[OH;D1;+0:8])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 11.0 mL acetone, diluted with 50 mL diethyl ether, is added dropwise to a solution of 500 mL of 0.25 molar 2,4-difluorobenzylmagnesium bromide in diethyl ether within 20 minutes. Then the mixture is refluxed for 1.5 hours and then hydrolyzed with 10% ammonium chloride solution. The ether phase is separated off, washed ... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone | Tertiary alcohol | null | null | c1ccccc1 | Br-.Mg | C(C)OCC | null | null | CC(C)=O.Fc1ccc([CH2][Mg][Br])c(F)c1>C(C)OCC>CC(C)(O)Cc1ccc(F)cc1F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-bc346cb941f340ce911683fe0edb2057 | CC(C)(Cc1ccc(F)cc1F)NC=O>>CC(C)(N)Cc1ccc(F)cc1F | FC1=C(C=CC(=C1)F)CC(C)(C)NC=O.Cl>>FC1=C(C=CC(=C1)F)CC(C)(C)N | O=C[NH:4][C:2]([CH3:1])([CH3:3])[CH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]1[F:13]>>[CH3:1][C:2]([CH3:3])([NH2:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]1[F:13] | CC(C)(Cc1ccc(F)cc1F)NC=O | CC(C)(N)Cc1ccc(F)cc1F | null | null | null | Reduction | Reduction of primary amides to amines | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccccc1 | O=C-[NH;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[C;D1;H3:5]>>[C:3]-[C:2](-[C;D1;H3:4])(-[C;D1;H3:5])-[NH2;D1;+0:1] | null | [] | null | null | null | null | Reaction of 22.0 g (100 mmol) of N-[2-(2,4-difluorophenyl]-1,1-dimethylethyl]formamide analogously to the method for Example 10(c). Yield: 16.0 g (72%, hydrochloride); melting point: 201° C.-203° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1 | Other | null | null | null | CC(C)(Cc1ccc(F)cc1F)NC=O>>CC(C)(N)Cc1ccc(F)cc1F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b7003b58f246402ea58147ad3ad85e78 | CC(C)(N)Cc1ccc(F)cc1F.CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2>>CC(C)(Cc1ccc(F)cc1F)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 | C(C1=CC=CC=C1)OC1OC2=C(NC1=O)C=CC=C2C(C(O)OCC)=O.FC1=C(C=CC(=C1)F)CC(C)(C)N.Cl>>C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=C(C=C(C=C1)F)F)(C)C)O | [CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[F:12])[NH2:13].CCO[CH:14](O)[C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:28][c:29]2[c:30]1[O:31][CH:32]([O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[C:33](=[O:34])[NH:35]2>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][c:8]([F:9])[cH:1... | CC(C)(N)Cc1ccc(F)cc1F.CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2 | CC(C)(Cc1ccc(F)cc1F)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e4b89399a4f55a0af960a37042cea8a8c75c6298d132f9a4be2364ae88492a84 | 4ef679604d0e977a363fff66519675c20f55f1d944c6c8949280ef4bc8f85467 | O=C1COc2c(CCNCCc3ccccc3)cc(OCc3ccccc3)cc2N1 | C-C-O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]1:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]2:[c:9]:1-[#8:10]-[CH;D3;+0:11](-[O;H0;D2;+0:12]-[C:13]-[c:14])-[C:15](=[O;D1;H0:16])-[#7:17]-2.[C:18]-[C:19](-[C;D1;H3:20])(-[C;D1;H3:21])-[NH2;D1;+0:22]>>[C:18]-[C:19](-[C;D1;H3:20])(-[C;D1;H3:21])-[NH;D2;+0:22]-[CH2;D2;+0:1]-... | null | [] | null | null | null | null | Reaction of 0.89 g (2.49 mmol) of benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 0.40 g (2.16 mmol) of 2-(2,4-difluorophenyl)-1,1-dimethylethylamine in the manner described for Example 8(d). Yield: 0.80 g (62%, hydrochloride); melting point 245° C.-247° C.
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Ether.Secondary alcohol.Primary amine | Ether.Ether.Secondary alcohol.Secondary amine | c1ccc2c(c1)NCCO2 | c1ccc2c(c1)NCCO2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)NCCO2 | HO- | null | null | null | CC(C)(N)Cc1ccc(F)cc1F.CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2>>CC(C)(Cc1ccc(F)cc1F)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f7612df1b54540428f756596601daa60 | CC(C)=O.Fc1cc(F)cc(CBr)c1>>CC(C)(O)Cc1cc(F)cc(F)c1 | FC=1C=C(CBr)C=C(C1)F.CC(=O)C>>FC=1C=C(C=C(C1)F)CC(C)(O)C | [CH3:1][C:2]([CH3:3])=[O:4].Br[CH2:5][c:6]1[cH:7][c:8]([F:9])[cH:10][c:11]([F:12])[cH:13]1>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][c:6]1[cH:7][c:8]([F:9])[cH:10][c:11]([F:12])[cH:13]1 | CC(C)=O.Fc1cc(F)cc(CBr)c1 | CC(C)(O)Cc1cc(F)cc(F)c1 | null | null | null | C-C Coupling | Grignard_alcohol | 769c01a2de8a052c306a223603a055dda0fdbaa49ef786ff9ffa9776720852e2 | afe96a58b8c6ca4e103c0c96e2a417cdee8e581054f8e646150ad555cb751905 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C;H0;D3;+0:6](-[C;D1;H3:7])=[O;H0;D1;+0:8]>>[C;D1;H3:5]-[C;H0;D4;+0:6](-[C;D1;H3:7])(-[OH;D1;+0:8])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The target compound is obtained by reacting a Grignard compound, prepared from 25.0 g (121 mmol) of 3,5-difluorobenzyl bromide, with 12.6 mL (171 mmol) of acetone. Yellow oil. Yield: 13.5 g (60%).
Conditions: See reaction.notes.procedure_details.
Workup: The target compound is obtained | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Tertiary alcohol | null | null | c1ccccc1 | Br- | null | null | null | CC(C)=O.Fc1cc(F)cc(CBr)c1>>CC(C)(O)Cc1cc(F)cc(F)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f8948b8c649845d886b448e7bc2c74df | CC(C)(N)Cc1cc(F)cc(F)c1.CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2>>CC(C)(Cc1cc(F)cc(F)c1)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 | C(C1=CC=CC=C1)OC1OC2=C(NC1=O)C=CC=C2C(C(O)OCC)=O.FC=1C=C(C=C(C1)F)CC(C)(C)N.Cl>>C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=CC(=CC(=C1)F)F)(C)C)O | [CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][c:7]([F:8])[cH:9][c:10]([F:11])[cH:12]1)[NH2:13].CCO[CH:14](O)[C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:28][c:29]2[c:30]1[O:31][CH:32]([O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[C:33](=[O:34])[NH:35]2>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][c:7]([F:8])[cH:9][c:... | CC(C)(N)Cc1cc(F)cc(F)c1.CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2 | CC(C)(Cc1cc(F)cc(F)c1)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e4b89399a4f55a0af960a37042cea8a8c75c6298d132f9a4be2364ae88492a84 | 4ef679604d0e977a363fff66519675c20f55f1d944c6c8949280ef4bc8f85467 | O=C1COc2c(CCNCCc3ccccc3)cc(OCc3ccccc3)cc2N1 | C-C-O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]1:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]2:[c:9]:1-[#8:10]-[CH;D3;+0:11](-[O;H0;D2;+0:12]-[C:13]-[c:14])-[C:15](=[O;D1;H0:16])-[#7:17]-2.[C:18]-[C:19](-[C;D1;H3:20])(-[C;D1;H3:21])-[NH2;D1;+0:22]>>[C:18]-[C:19](-[C;D1;H3:20])(-[C;D1;H3:21])-[NH;D2;+0:22]-[CH2;D2;+0:1]-... | null | [] | null | null | null | null | Prepared from 1.73 g (4.84 mmol) of benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 0.80 g (4.32 mmol) of 2-(3,5-difluorophenyl)-1,1-dimethylethylamine in the usual way. Yield: 1.50 g (58%, hydrochloride); melting point: 240° C.-244° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Ether.Secondary alcohol.Primary amine | Ether.Ether.Secondary alcohol.Secondary amine | c1ccc2c(c1)NCCO2 | c1ccc2c(c1)NCCO2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)NCCO2 | HO- | null | null | null | CC(C)(N)Cc1cc(F)cc(F)c1.CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2>>CC(C)(Cc1cc(F)cc(F)c1)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-60a013527aac4b50984d7d3bd4bf5694 | CCOC(O)C(=O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2.CCOc1ccc(CC(C)(C)N)cc1>>CCOc1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1 | CC(=O)C.C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(C(O)OCC)=O.C(C)OC1=CC=C(C=C1)CC(C)(C)N.[BH4-].[Na+]>>C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=CC=C(C=C1)OCC)(C)C)O | CCO[CH:13](O)[C:14](=[O:15])[c:16]1[cH:17][c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:27][c:28]2[c:29]1[O:30][CH2:31][C:32](=[O:33])[NH:34]2.[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][C:9]([CH3:10])([CH3:11])[NH2:12])[cH:35][cH:36]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][C:... | CCOC(O)C(=O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2.CCOc1ccc(CC(C)(C)N)cc1 | CCOc1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1 | null | null | C(C)(=O)O.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 1fdebd18d8e186352a5054d1639a246066c291a759c2941bdb27defc05ab0b96 | 270f718637e505454980bf4a24a04f3a3a166f4d4160855797b4e1923ac25b66 | O=C1COc2c(CCNCCc3ccccc3)cc(OCc3ccccc3)cc2N1 | C-C-O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6]-[#8:7].[C:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[NH2;D1;+0:12]>>[#8:7]-[c:6]:[c:4](-[CH;D3;+0:2](-[OH;D1;+0:3])-[CH2;D2;+0:1]-[NH;D2;+0:12]-[C:9](-[C:8])(-[C;D1;H3:10])-[C;D1;H3:11]):[c:5] | null | [] | null | null | null | null | 2.14 g (6.0 mmol) of 6-benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 1.0 g (5.2 mmol) of 2-(4-ethoxyphenyl)-1,1-dimethylethylamine are stirred in 40 mL ethanol for one hour at 50° C.-80° C. After cooling to ambient temperature, 0.23 g (6.0 mmol) of sodium borohydride are added and the mixture is ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Secondary alcohol.Primary amine | Secondary alcohol.Secondary amine | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)NCCO2 | HO- | C(C)(=O)O.C(C)O | null | null | CCOC(O)C(=O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2.CCOc1ccc(CC(C)(C)N)cc1>C(C)(=O)O.C(C)O>CCOc1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6c1e7ebe7ac64f5ca4ace310742af500 | CCOc1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1>>CCOc1ccc(CC(C)(C)NCC(O)c2cc(O)cc3c2OCC(=O)N3)cc1 | C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=CC=C(C=C1)OCC)(C)C)O>>C(C)OC1=CC=C(C=C1)CC(C)(C)NCC(O)C1=CC(=CC=2NC(COC21)=O)O | c1ccc(C[O:19][c:18]2[cH:17][c:16]([CH:14]([CH2:13][NH:12][C:9]([CH2:8][c:7]3[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:29][cH:28]3)([CH3:10])[CH3:11])[OH:15])[c:22]3[c:21]([cH:20]2)[NH:27][C:25](=[O:26])[CH2:24][O:23]3)cc1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][C:9]([CH3:10])([CH3:11])[NH:12][CH2:13][CH:14]... | CCOc1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1 | CCOc1ccc(CC(C)(C)NCC(O)c2cc(O)cc3c2OCC(=O)N3)cc1 | null | [Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1COc2c(CCNCCc3ccccc3)cccc2N1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | null | null | 1.5 g (2.8 mmol) of 6-benzyloxy-8-{2-[2-(4-ethoxyphenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-4H-benzo[1,4]oxazin-3-one in 80 mL methanol are hydrogenated with 250 mg palladium on charcoal (10%) as catalyst at ambient temperature and normal pressure. The catalyst is suction filtered and the filtrate is evaporated do... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)NCCO2 | Other | [Pd].CO | null | null | CCOc1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1>[Pd].CO>CCOc1ccc(CC(C)(C)NCC(O)c2cc(O)cc3c2OCC(=O)N3)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-cee3b1257d7f45e59f2a7498651adc5e | Cc1cc(C)cc(CC(C)(C)NC=O)c1>>Cc1cc(C)cc(CC(C)(C)N)c1 | CC=1C=C(C=C(C1)C)CC(C)(C)NC=O.Cl>>CC=1C=C(C=C(C1)C)CC(C)(C)N | O=C[NH:12][C:9]([CH2:8][c:7]1[cH:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:13]1)([CH3:10])[CH3:11]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([CH2:8][C:9]([CH3:10])([CH3:11])[NH2:12])[cH:13]1 | Cc1cc(C)cc(CC(C)(C)NC=O)c1 | Cc1cc(C)cc(CC(C)(C)N)c1 | null | null | null | Reduction | Reduction of primary amides to amines | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccccc1 | O=C-[NH;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[C;D1;H3:5]>>[C:3]-[C:2](-[C;D1;H3:4])(-[C;D1;H3:5])-[NH2;D1;+0:1] | null | [] | null | null | null | null | By reacting 6.00 g (34 mmol) of 1-(3,5-dimethylphenyl)-2-methylpropanol-2-ol and 2.00 g (41 mmol) of sodium cyanide in a Ritter reaction, 2.40 g of 2-(3,5-dimethylphenyl)-1,1-dimethylethylformamide (35% yield) is obtained. To liberate the amine, the formamide (2.40 g, 11.7 mmol) is treated with hydrochloric acid. The m... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1 | Other | null | null | null | Cc1cc(C)cc(CC(C)(C)NC=O)c1>>Cc1cc(C)cc(CC(C)(C)N)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b454d9d260ae437a8d51681e85463c20 | CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2.Cc1cc(C)cc(CC(C)(C)N)c1>>Cc1cc(C)cc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)c1 | C(C1=CC=CC=C1)OC1OC2=C(NC1=O)C=CC=C2C(C(O)OCC)=O.CC=1C=C(C=C(C1)C)CC(C)(C)N.Cl>>C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=CC(=CC(=C1)C)C)(C)C)O | CCO[CH:13](O)[C:14](=[O:15])[c:16]1[cH:17][cH:18][cH:27][c:28]2[c:29]1[O:30][CH:31]([O:19][CH2:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1)[C:32](=[O:33])[NH:34]2.[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([CH2:8][C:9]([CH3:10])([CH3:11])[NH2:12])[cH:35]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([CH2:8][C:9](... | CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2.Cc1cc(C)cc(CC(C)(C)N)c1 | Cc1cc(C)cc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e4b89399a4f55a0af960a37042cea8a8c75c6298d132f9a4be2364ae88492a84 | 4ef679604d0e977a363fff66519675c20f55f1d944c6c8949280ef4bc8f85467 | O=C1COc2c(CCNCCc3ccccc3)cc(OCc3ccccc3)cc2N1 | C-C-O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]1:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]2:[c:9]:1-[#8:10]-[CH;D3;+0:11](-[O;H0;D2;+0:12]-[C:13]-[c:14])-[C:15](=[O;D1;H0:16])-[#7:17]-2.[C:18]-[C:19](-[C;D1;H3:20])(-[C;D1;H3:21])-[NH2;D1;+0:22]>>[C:18]-[C:19](-[C;D1;H3:20])(-[C;D1;H3:21])-[NH;D2;+0:22]-[CH2;D2;+0:1]-... | null | [] | null | null | null | null | Prepared analogously to the method for Example 8(d) from 1.47 g (4.1 mmol) of benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 0.65 g (3.7 mmol) of 2-(3,5-dimethylphenyl)-1,1-dimethylethylamine. Yield: 1.1 g (51%, hydrochloride); melting point: 220° C.-222° C.
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Ether.Secondary alcohol.Primary amine | Ether.Ether.Secondary alcohol.Secondary amine | c1ccc2c(c1)NCCO2 | c1ccc2c(c1)NCCO2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)NCCO2 | HO- | null | null | null | CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2.Cc1cc(C)cc(CC(C)(C)N)c1>>Cc1cc(C)cc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5f64649a2d3343dca5f41288ea2360de | Cc1cc(C)cc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)c1>>Cc1cc(C)cc(CC(C)(C)NCC(O)c2cc(O)cc3c2OCC(=O)N3)c1 | C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=CC(=CC(=C1)C)C)(C)C)O.Cl>>CC=1C=C(C=C(C1)C)CC(C)(C)NCC(O)C1=CC(=CC=2NC(COC21)=O)O | c1ccc(C[O:19][c:18]2[cH:17][c:16]([CH:14]([CH2:13][NH:12][C:9]([CH2:8][c:7]3[cH:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:28]3)([CH3:10])[CH3:11])[OH:15])[c:22]3[c:21]([cH:20]2)[NH:27][C:25](=[O:26])[CH2:24][O:23]3)cc1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7]([CH2:8][C:9]([CH3:10])([CH3:11])[NH:12][CH2:13][CH:14]([O... | Cc1cc(C)cc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)c1 | Cc1cc(C)cc(CC(C)(C)NCC(O)c2cc(O)cc3c2OCC(=O)N3)c1 | null | null | C(C)(C)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1COc2c(CCNCCc3ccccc3)cccc2N1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | null | null | The target compound was obtained after hydrogenolysis of 0.90 g (1.71 mmol) of 6-benzyloxy-8-{2-[2-(3,5-dimethylphenyl)-1,1-dimethylethylamino]-1-hydroxyethyl}-4H-benzo[1,4]oxazin-3-one and recrystallization of the crude product from isopropanol. White solid. Yield: 0.50 g (69%, hydrochloride); melting point: 235° C.-2... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)NCCO2 | Other | C(C)(C)O | null | null | Cc1cc(C)cc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)c1>C(C)(C)O>Cc1cc(C)cc(CC(C)(C)NCC(O)c2cc(O)cc3c2OCC(=O)N3)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5a2192e832a041c4a49798e2954a8d2e | CCOC(=O)CCCOc1ccc(CC(C)(C)N)cc1.CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2>>CCOC(=O)CCCOc1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1 | O.C(C1=CC=CC=C1)OC1OC2=C(NC1=O)C=CC=C2C(C(O)OCC)=O.NC(CC1=CC=C(OCCCC(=O)OCC)C=C1)(C)C.C(C(=O)O)(=O)O>>C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=CC=C(OCCCC(=O)OCC)C=C1)(C)C)O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][C:15]([CH3:16])([CH3:17])[NH2:18])[cH:41][cH:42]1.CCO[CH:19](O)[C:20](=[O:21])[c:22]1[cH:23][cH:24][cH:33][c:34]2[c:35]1[O:36][CH:37]([O:25][CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1)[C:38](=[O:39])[NH:40]2>>[CH3:1][... | CCOC(=O)CCCOc1ccc(CC(C)(C)N)cc1.CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2 | CCOC(=O)CCCOc1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1 | null | null | C(C)(=O)OCC.C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | e4b89399a4f55a0af960a37042cea8a8c75c6298d132f9a4be2364ae88492a84 | 4ef679604d0e977a363fff66519675c20f55f1d944c6c8949280ef4bc8f85467 | O=C1COc2c(CCNCCc3ccccc3)cc(OCc3ccccc3)cc2N1 | C-C-O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]1:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]2:[c:9]:1-[#8:10]-[CH;D3;+0:11](-[O;H0;D2;+0:12]-[C:13]-[c:14])-[C:15](=[O;D1;H0:16])-[#7:17]-2.[C:18]-[C:19](-[C;D1;H3:20])(-[C;D1;H3:21])-[NH2;D1;+0:22]>>[C:18]-[C:19](-[C;D1;H3:20])(-[C;D1;H3:21])-[NH;D2;+0:22]-[CH2;D2;+0:1]-... | null | [] | null | null | null | null | 1.20 g (3.36 mmol) of benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 0.90 g (3.22 mmol) of ethyl 4-[4-(2-amino-2-methylpropyl)phenoxy]butyrate are reacted in the manner described for Example 8(d). The crude product is dissolved in 10 mL ethyl acetate and 10 mL water and combined with oxalic acid w... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Ether.Secondary alcohol.Primary amine | Ether.Ether.Secondary alcohol.Secondary amine | c1ccc2c(c1)NCCO2 | c1ccc2c(c1)NCCO2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)NCCO2 | HO- | C(C)(=O)OCC.C(C)OCC | null | null | CCOC(=O)CCCOc1ccc(CC(C)(C)N)cc1.CCOC(O)C(=O)c1cccc2c1OC(OCc1ccccc1)C(=O)N2>C(C)(=O)OCC.C(C)OCC>CCOC(=O)CCCOc1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-db2eb28b40bd4d06ac41f90d4b5af7df | CCOC(=O)CCCOc1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1>>CC(C)(Cc1ccc(OCCCC(=O)O)cc1)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 | C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=CC=C(OCCCC(=O)OCC)C=C1)(C)C)O.[OH-].[Na+].Cl>>C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=CC=C(OCCCC(=O)O)C=C1)(C)C)O | CC[O:15][C:13]([CH2:12][CH2:11][CH2:10][O:9][c:8]1[cH:7][cH:6][c:5]([CH2:4][C:2]([CH3:1])([CH3:3])[NH:18][CH2:19][CH:20]([OH:21])[c:22]2[cH:23][c:24]([O:25][CH2:26][c:27]3[cH:28][cH:29][cH:30][cH:31][cH:32]3)[cH:33][c:34]3[c:35]2[O:36][CH2:37][C:38](=[O:39])[NH:40]3)[cH:17][cH:16]1)=[O:14]>>[CH3:1][C:2]([CH3:3])([CH2:4... | CCOC(=O)CCCOc1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1 | CC(C)(Cc1ccc(OCCCC(=O)O)cc1)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1COc2c(CCNCCc3ccccc3)cc(OCc3ccccc3)cc2N1 | 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] | null | [] | null | null | null | null | A solution of 1.00 g (1.73 mmol) of ethyl 4-(4-{2-[2-(6-benzyloxy-3-oxo-3,4-dihydro-2H-benzo [1,4]oxazin-8-yl)-2-hydroxyethylamino]-2-methylpropyl}phenoxy)butyrate in 25 mL methanol is combined with 2.5 mL of 1 N sodium hydroxide solution, refluxed for 30 minutes, and then neutralized with 1 N hydrochloric acid. The so... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)NCCO2 | Other | CO | null | null | CCOC(=O)CCCOc1ccc(CC(C)(C)NCC(O)c2cc(OCc3ccccc3)cc3c2OCC(=O)N3)cc1>CO>CC(C)(Cc1ccc(OCCCC(=O)O)cc1)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c6cafa93917c42c8b547e46c7f1577f2 | CC(C)(Cc1ccc(OCCCC(=O)O)cc1)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2>>CC(C)(Cc1ccc(OCCCC(=O)O)cc1)NCC(O)c1cc(O)cc2c1OCC(=O)N2 | C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(CNC(CC1=CC=C(OCCCC(=O)O)C=C1)(C)C)O.C(C)(=O)O>>OC(CNC(CC1=CC=C(OCCCC(=O)O)C=C1)(C)C)C1=CC(=CC=2NC(COC21)=O)O | c1ccc(C[O:25][c:24]2[cH:23][c:22]([CH:20]([CH2:19][NH:18][C:2]([CH3:1])([CH3:3])[CH2:4][c:5]3[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][C:13](=[O:14])[OH:15])[cH:16][cH:17]3)[OH:21])[c:28]3[c:27]([cH:26]2)[NH:33][C:31](=[O:32])[CH2:30][O:29]3)cc1>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][... | CC(C)(Cc1ccc(OCCCC(=O)O)cc1)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 | CC(C)(Cc1ccc(OCCCC(=O)O)cc1)NCC(O)c1cc(O)cc2c1OCC(=O)N2 | null | [Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1COc2c(CCNCCc3ccccc3)cccc2N1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | null | null | 0.70 g (1.28 mmol) of 4-(4-{2-[2-(6-benzyloxy-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin -8-yl)-2-hydroxyethylamino]-2-methylpropyl}phenoxy)butyric acid is dissolved in 25 mL methanol and 2 mL acetic acid and hydrogenated in the presence of 150 mg palladium on charcoal (10%) at ambient temperature and normal pressure. The c... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)NCCO2 | Other | [Pd].CO | null | null | CC(C)(Cc1ccc(OCCCC(=O)O)cc1)NCC(O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2>[Pd].CO>CC(C)(Cc1ccc(OCCCC(=O)O)cc1)NCC(O)c1cc(O)cc2c1OCC(=O)N2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-72dec086166f4873afdcae84023e3b58 | CC(C)=O.Fc1ccc(CBr)cc1F>>CC(C)(O)Cc1ccc(F)c(F)c1 | FC=1C=C(CBr)C=CC1F.CC(=O)C>>FC=1C=C(C=CC1F)CC(C)(O)C | [CH3:1][C:2]([CH3:3])=[O:4].Br[CH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[cH:13]1>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[cH:13]1 | CC(C)=O.Fc1ccc(CBr)cc1F | CC(C)(O)Cc1ccc(F)c(F)c1 | null | null | null | C-C Coupling | Grignard_alcohol | 769c01a2de8a052c306a223603a055dda0fdbaa49ef786ff9ffa9776720852e2 | afe96a58b8c6ca4e103c0c96e2a417cdee8e581054f8e646150ad555cb751905 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C;H0;D3;+0:6](-[C;D1;H3:7])=[O;H0;D1;+0:8]>>[C;D1;H3:5]-[C;H0;D4;+0:6](-[C;D1;H3:7])(-[OH;D1;+0:8])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | From 23.0 g (111 mmol) of 3,4-difluorobenzyl bromide a Grignard is prepared, which is then reacted with 11.6 mL (158 mmol) of acetone. Slightly yellow oil. Yield: 9.7 g (47%); Rf value: 0.55 (ethyl acetate-petroleum ether (1:3)).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Tertiary alcohol | null | null | c1ccccc1 | Br- | null | null | null | CC(C)=O.Fc1ccc(CBr)cc1F>>CC(C)(O)Cc1ccc(F)c(F)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-86e31ac1b8354a41b096ba2134231c71 | CC(C)(Cc1ccc(F)c(F)c1)NC=O>>CC(C)(N)Cc1ccc(F)c(F)c1 | FC=1C=C(C=CC1F)CC(C)(C)NC=O.Cl.[OH-].[Na+]>>FC=1C=C(C=CC1F)CC(C)(C)N | O=C[NH:4][C:2]([CH3:1])([CH3:3])[CH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[cH:13]1>>[CH3:1][C:2]([CH3:3])([NH2:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([F:10])[c:11]([F:12])[cH:13]1 | CC(C)(Cc1ccc(F)c(F)c1)NC=O | CC(C)(N)Cc1ccc(F)c(F)c1 | null | null | C(C)O | Reduction | Reduction of primary amides to amines | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccccc1 | O=C-[NH;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[C;D1;H3:5]>>[C:3]-[C:2](-[C;D1;H3:4])(-[C;D1;H3:5])-[NH2;D1;+0:1] | null | [] | null | null | null | null | 4.00 g (18.5 mmol) of N-[2-(3,4-difluorophenyl)-1,1-dimethylethyl]formamide is dissolved in ethanol, combined with concentrated hydrochloric acid, and refluxed overnight. The reaction solution is poured onto ice water, made alkaline with sodium hydroxide, and extracted with tert-butylmethyl ether. The organic phases ar... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1 | Other | C(C)O | null | null | CC(C)(Cc1ccc(F)c(F)c1)NC=O>C(C)O>CC(C)(N)Cc1ccc(F)c(F)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4441e79696ac40c1bf0f8abad85e67ee | CC(C)(N)Cc1ccc(F)c(F)c1.CCOC(O)C(=O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2>>CC(C)(Cc1ccc(F)c(F)c1)NCC(O)c1cc(O)cc2c1OCC(=O)N2 | [BH4-].[Li+].C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(C(O)OCC)=O.FC=1C=C(C=CC1F)CC(C)(C)N.ClCCl>>FC=1C=C(C=CC1F)CC(C)(C)NCC(O)C1=CC(=CC=2NC(COC21)=O)O | [CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][c:8]([F:9])[c:10]([F:11])[cH:12]1)[NH2:13].CCO[CH:14](O)[C:15](=[O:16])[c:17]1[cH:18][c:19]([O:20]Cc2ccccc2)[cH:21][c:22]2[c:23]1[O:24][CH2:25][C:26](=[O:27])[NH:28]2>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][c:8]([F:9])[c:10]([F:11])[cH:12]1)[NH:13][CH2:14][CH:15]... | CC(C)(N)Cc1ccc(F)c(F)c1.CCOC(O)C(=O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 | CC(C)(Cc1ccc(F)c(F)c1)NCC(O)c1cc(O)cc2c1OCC(=O)N2 | null | null | O.O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 04b439b3d895bbd6faf5428ecaae08a7adc8582b70157632abf55ece87447157 | ae7a1cd46b7f191be3befe95a798401405d2a42119bcb446aadd68bc9a1bd326 | O=C1COc2c(CCNCCc3ccccc3)cccc2N1 | C-C-O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]:[c:6](-[O;H0;D2;+0:7]-C-c1:c:c:c:c:c:1):[c:8]):[c:9]-[#8:10].[C:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[NH2;D1;+0:15]>>[#8:10]-[c:9]:[c:4](-[CH;D3;+0:2](-[OH;D1;+0:3])-[CH2;D2;+0:1]-[NH;D2;+0:15]-[C:12](-[C:11])(-[C;D1;H3:13])-[C;D1;H3:14]):[c:5]:[c:... | null | [] | 0 | CELSIUS | 30 | MINUTE | 357 mg (1 mmol) of 6-benzyloxy-8-(2-ethoxy-2-hydroxy-acetyl)-4H-benzo[1,4]oxazin-3-one and 185 mg (1 mmol) of 2-(3,4-difluorophenyl)-1,1-dimethylethylamine are stirred for 30 minutes in 5 mL tetrahydrofuran at ambient temperature. It is cooled to 0° C. and, under an argon atmosphere, 1.5 mL of a 2 molar solution of lit... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Secondary alcohol.Primary amine | Secondary alcohol.Aromatic alcohol.Secondary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)NCCO2 | HO- | O.O1CCCC1 | 0 | 0.5 | CC(C)(N)Cc1ccc(F)c(F)c1.CCOC(O)C(=O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2>O.O1CCCC1>CC(C)(Cc1ccc(F)c(F)c1)NCC(O)c1cc(O)cc2c1OCC(=O)N2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-68992909e6e54c8bb9f71e7686ac5303 | CC(C)(N)Cc1ccc(F)cc1Cl.CCOC(O)C(=O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2>>CC(C)(Cc1ccc(F)cc1Cl)NCC(O)c1cc(O)cc2c1OCC(=O)N2 | C(O)CN.C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(C(O)OCC)=O.ClC1=C(C=CC(=C1)F)CC(C)(C)N.[BH4-].[Li+].B(Br)(Br)Br>>ClC1=C(C=CC(=C1)F)CC(C)(C)NCC(O)C1=CC(=CC=2NC(COC21)=O)O | [CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[Cl:12])[NH2:13].CCO[CH:14](O)[C:15](=[O:16])[c:17]1[cH:18][c:19]([O:20]Cc2ccccc2)[cH:21][c:22]2[c:23]1[O:24][CH2:25][C:26](=[O:27])[NH:28]2>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[Cl:12])[NH:13][CH2:14][CH:15]([... | CC(C)(N)Cc1ccc(F)cc1Cl.CCOC(O)C(=O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2 | CC(C)(Cc1ccc(F)cc1Cl)NCC(O)c1cc(O)cc2c1OCC(=O)N2 | null | null | ClCCl.O | Heteroatom Alkylation and Arylation | OtherReaction | 04b439b3d895bbd6faf5428ecaae08a7adc8582b70157632abf55ece87447157 | ae7a1cd46b7f191be3befe95a798401405d2a42119bcb446aadd68bc9a1bd326 | O=C1COc2c(CCNCCc3ccccc3)cccc2N1 | C-C-O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]:[c:6](-[O;H0;D2;+0:7]-C-c1:c:c:c:c:c:1):[c:8]):[c:9]-[#8:10].[C:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[NH2;D1;+0:15]>>[#8:10]-[c:9]:[c:4](-[CH;D3;+0:2](-[OH;D1;+0:3])-[CH2;D2;+0:1]-[NH;D2;+0:15]-[C:12](-[C:11])(-[C;D1;H3:13])-[C;D1;H3:14]):[c:5]:[c:... | null | [] | -78 | CELSIUS | null | null | 357 mg (1 mmol) of 6-benzyloxy-8-(2-ethoxy-2-hydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 202 mg (1 mmol) of 2-(2-chloro-4-fluorophenyl)-1,1-dimethylethylamine are reacted with lithium borohydride analogously to the method for Example 10(d). To debenzylate the ethanolamine thus obtained, it is dissolved in 3 mL of dich... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Secondary alcohol.Primary amine | Secondary alcohol.Aromatic alcohol.Secondary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)NCCO2 | HO- | ClCCl.O | -78 | null | CC(C)(N)Cc1ccc(F)cc1Cl.CCOC(O)C(=O)c1cc(OCc2ccccc2)cc2c1OCC(=O)N2>ClCCl.O>CC(C)(Cc1ccc(F)cc1Cl)NCC(O)c1cc(O)cc2c1OCC(=O)N2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-07cf27db35be458b8df1e8c9dafe6b6e | CC(C)(N)Cc1ccc(Br)cc1.O=C1COc2c(cc(OCc3ccccc3)cc2C(=O)C(O)O)N1>>CC(C)(Cc1ccc(Br)cc1)NCC(O)c1cc(O)cc2c1OCC(=O)N2 | C(O)CN.C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(C(O)O)=O.BrC1=CC=C(C=C1)CC(C)(C)N>>BrC1=CC=C(C=C1)CC(C)(C)NCC(O)C1=CC(=CC=2NC(COC21)=O)O | [CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1)[NH2:12].O[CH:13](O)[C:14](=[O:15])[c:16]1[cH:17][c:18]([O:19]Cc2ccccc2)[cH:20][c:21]2[c:22]1[O:23][CH2:24][C:25](=[O:26])[NH:27]2>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1)[NH:12][CH2:13][CH:14]([OH:15])[c:16... | CC(C)(N)Cc1ccc(Br)cc1.O=C1COc2c(cc(OCc3ccccc3)cc2C(=O)C(O)O)N1 | CC(C)(Cc1ccc(Br)cc1)NCC(O)c1cc(O)cc2c1OCC(=O)N2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2f30b2ddfd3165049895fad12b56e7045a65b9fb994cf98033b34a0da07921b0 | f770f31138008786eba8b848b4fc2239127c6f6923d9ae1afd24b547ecc22539 | O=C1COc2c(CCNCCc3ccccc3)cccc2N1 | O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]:[c:6](-[O;H0;D2;+0:7]-C-c1:c:c:c:c:c:1):[c:8]):[c:9]-[#8:10].[C:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[NH2;D1;+0:15]>>[#8:10]-[c:9]:[c:4](-[CH;D3;+0:2](-[OH;D1;+0:3])-[CH2;D2;+0:1]-[NH;D2;+0:15]-[C:12](-[C:11])(-[C;D1;H3:13])-[C;D1;H3:14]):[c:5]:[c:6](-... | null | [] | null | null | null | null | The preparation of the ethanolamine and debenzylation were carried out as described in Example 19 from 300 mg (0.91 mmol) of 6-benzyloxy-8-(2,2-dihydroxy-acetyl)-4H-benzo[1,4]oxazin-3-one and 250 mg (1.09 mmol) of 2-(4-bromophenyl)-1,1-dimethylethylamine. Beige solid. Yield: 54 mg (14%); mass spectrometry: [M+H]+=435, ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Secondary alcohol.Secondary alcohol.Primary amine | Secondary alcohol.Aromatic alcohol.Secondary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)NCCO2 | HO- | null | null | null | CC(C)(N)Cc1ccc(Br)cc1.O=C1COc2c(cc(OCc3ccccc3)cc2C(=O)C(O)O)N1>>CC(C)(Cc1ccc(Br)cc1)NCC(O)c1cc(O)cc2c1OCC(=O)N2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b71c40ec675c45b69826f0b263f21708 | CC(C)(N)Cc1ccc(F)cc1.O=C1COc2c(cc(OCc3ccccc3)cc2C(=O)C(O)O)N1>>CC(C)(Cc1ccc(F)cc1)NCC(O)c1cc(O)cc2c1OCC(=O)N2 | C(O)([O-])=O.[Na+].C(C1=CC=CC=C1)OC=1C=C(C2=C(NC(CO2)=O)C1)C(C(O)O)=O.FC1=CC=C(C=C1)CC(C)(C)N.[BH4-].[Na+]>>FC1=CC=C(C=C1)CC(C)(C)NCC(O)C1=CC(=CC=2NC(COC21)=O)O | [CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1)[NH2:12].O[CH:13](O)[C:14](=[O:15])[c:16]1[cH:17][c:18]([O:19]Cc2ccccc2)[cH:20][c:21]2[c:22]1[O:23][CH2:24][C:25](=[O:26])[NH:27]2>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]1)[NH:12][CH2:13][CH:14]([OH:15])[c:16]1... | CC(C)(N)Cc1ccc(F)cc1.O=C1COc2c(cc(OCc3ccccc3)cc2C(=O)C(O)O)N1 | CC(C)(Cc1ccc(F)cc1)NCC(O)c1cc(O)cc2c1OCC(=O)N2 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 2f30b2ddfd3165049895fad12b56e7045a65b9fb994cf98033b34a0da07921b0 | f770f31138008786eba8b848b4fc2239127c6f6923d9ae1afd24b547ecc22539 | O=C1COc2c(CCNCCc3ccccc3)cccc2N1 | O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]:[c:6](-[O;H0;D2;+0:7]-C-c1:c:c:c:c:c:1):[c:8]):[c:9]-[#8:10].[C:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[NH2;D1;+0:15]>>[#8:10]-[c:9]:[c:4](-[CH;D3;+0:2](-[OH;D1;+0:3])-[CH2;D2;+0:1]-[NH;D2;+0:15]-[C:12](-[C:11])(-[C;D1;H3:13])-[C;D1;H3:14]):[c:5]:[c:6](-... | null | [] | 80 | CELSIUS | 1 | HOUR | 300 mg (0.91 mmol) of 6-benzyloxy-8-(2,2-dihydroxyacetyl)-4H-benzo[1,4]oxazin-3-one and 183 mg (1.09 mmol) of 2-(4-fluorophenyl)-1,1-dimethylethylamine were dissolved in 3 mL of ethanol. Molecular sieve was added and the mixture was heated to 80° C. for 30 minutes. After cooling to ambient temperature, 35 mg (0.91 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Secondary alcohol.Secondary alcohol.Primary amine | Secondary alcohol.Aromatic alcohol.Secondary amine | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)NCCO2 | HO- | C(C)O | 80 | 1 | CC(C)(N)Cc1ccc(F)cc1.O=C1COc2c(cc(OCc3ccccc3)cc2C(=O)C(O)O)N1>C(C)O>CC(C)(Cc1ccc(F)cc1)NCC(O)c1cc(O)cc2c1OCC(=O)N2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f033fc08e413473e9aec011917a7adb6 | Nc1ccc(Br)cn1.O=C(Cl)c1ccccc1[N+](=O)[O-]>>O=C(Nc1ccc(Br)cn1)c1ccccc1[N+](=O)[O-] | [N+](=O)([O-])C1=C(C(=O)Cl)C=CC=C1.NC1=NC=C(C=C1)Br.N1=CC=CC=C1>>BrC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)[N+](=O)[O-] | [NH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][n:10]1.Cl[C:2](=[O:1])[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[N+:17](=[O:18])[O-:19]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][n:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][c:16]1[N+:17](=[O:18])[O-:19] | Nc1ccc(Br)cn1.O=C(Cl)c1ccccc1[N+](=O)[O-] | O=C(Nc1ccc(Br)cn1)c1ccccc1[N+](=O)[O-] | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccn1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:3](:[c:4]):[c:5] | 77.9 | [{"value": 77.0, "product": "BrC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.9, "product": "BrC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-nitrobenzoyl chloride (3.70 g, 20 mmol, 1.0 equiv), 2-amino-5-bromopyridine (3.50 g, 1.0 equiv), pyridine (10 mL) in 25 mL of methylene chloride was stirred overnight. The volatile was evaporated, flash chromatography on silica gel gave N-(5-bromo-2-pyridinyl)-(2-nitro)phenylcarboxamide (5.02 g, 77%). M... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1 | HCl | C(Cl)Cl | null | null | Nc1ccc(Br)cn1.O=C(Cl)c1ccccc1[N+](=O)[O-]>C(Cl)Cl>O=C(Nc1ccc(Br)cn1)c1ccccc1[N+](=O)[O-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6e554be1ffae496eb14a7491361f0fb0 | CC1=CC(=O)OC1=O.Nc1ccc(Br)cn1>>CC1=CC(=O)N(c2ccc(Br)cn2)C1=O | C1(\C(\C)=C/C(=O)O1)=O.NC1=NC=C(C=C1)Br>>BrC=1C=CC(=NC1)N1C(C(=CC1=O)C)=O | O1[C:4](=[O:5])[CH:3]=[C:2]([CH3:1])[C:14]1=[O:15].[NH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][n:13]1>>[CH3:1][C:2]1=[CH:3][C:4](=[O:5])[N:6]([c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][n:13]2)[C:14]1=[O:15] | CC1=CC(=O)OC1=O.Nc1ccc(Br)cn1 | CC1=CC(=O)N(c2ccc(Br)cn2)C1=O | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | cab1acd179957d4f5c27ba23f314ee257f7d508deff2838c7964b1019063e651 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C=CC(=O)N1c1ccccn1 | [C;D1;H3:1]-[C:2]1=[C:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-O-[C;H0;D3;+0:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[C;D1;H3:1]-[C:2]1=[C:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:8](-[c:9](:[c:10]):[#7;a:11]:[c:12])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | 71 | [{"value": 71.0, "product": "BrC=1C=CC(=NC1)N1C(C(=CC1=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.8, "product": "BrC=1C=CC(=NC1)N1C(C(=CC1=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of citraconic anhydride (1.00 mL, 11.1 mmol) and 2-amino-5-bromopyridine (1.93 g, 11.2 mmol) in toluene (60 mL) was heated to reflux overnight. The solution was cooled down, filtered. The filtrate was concentrated in vacuo to give a solid (2.10 g, yield: 71%). MS 267 and 269 (M+H).
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1=CCOC1 | C1=CC[NH]C1 | C1=CC[NH]C1.c1ccncc1 | HO- | C1(=CC=CC=C1)C | null | null | CC1=CC(=O)OC1=O.Nc1ccc(Br)cn1>C1(=CC=CC=C1)C>CC1=CC(=O)N(c2ccc(Br)cn2)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8d1da3bc63a34c6499333c394caf4bb7 | Nc1ccc(Cl)cn1.O=c1[nH]c2ccc(Cl)cc2c(=O)o1>>Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 | ClC1=CC=C2C(C(=O)OC(N2)=O)=C1.NC1=NC=C(C=C1)Cl.C[Si](C)(C)[N-][Si](C)(C)C.[K+].C1(=CC=CC=C1)C>>NC1=C(C=C(C=C1)Cl)C(=O)NC1=NC=C(C=C1)Cl | [NH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][n:18]1.O=c1o[c:9](=[O:10])[c:8]2[c:2]([nH:1]1)[cH:3][cH:4][c:5]([Cl:6])[cH:7]2>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][n:18]1 | Nc1ccc(Cl)cn1.O=c1[nH]c2ccc(Cl)cc2c(=O)o1 | Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 | null | null | O1CCCC1 | Acylation | OtherReaction | b4c245015e48b9b60756b62e3f8985928af86452315d98417a25faace320d9ae | b609a70ccab739990a9ccc4ea2adcc77011bcd0c07154489a12420f7c0e7382e | O=C(Nc1ccccn1)c1ccccc1 | O=c1:[nH;D2;+0:1]:[c:2](:[c:3]):[c:4](:[c:5]):[c;H0;D3;+0:6](=[O;D1;H0:7]):o:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]):[c:5] | 100 | [{"value": 100.0, "product": "NC1=C(C=C(C=C1)Cl)C(=O)NC1=NC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.7, "product": "NC1=C(C=C(C=C1)Cl)C(=O)NC1=NC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 0.5 | HOUR | To a solution of 2-amino-5-chloropyridine (328 mg, 2.55 mmol) in tetrahydrofuran (5 ml) was 0.5M potassium bis(trimethylsilyl)amide in toluene (10 ml, 5.05 mmol) dropwise at −78° C. After stirred for additional 0.5 hr at −78° C., the mixture was added 5-chloroisatoic anhydride (0.5 g, 2.55 mmol) at −78° C. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide.Primary amine | c1ccc2ncocc2c1 | c1ccccc1 | c1ccccc1.c1ccncc1 | Other | O1CCCC1 | -78 | 0.5 | Nc1ccc(Cl)cn1.O=c1[nH]c2ccc(Cl)cc2c(=O)o1>O1CCCC1>Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-817195682fd24d17ad8fd66308dccb42 | CNCCN.N#Cc1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1>>CN1CCN=C1c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | CNCCN.ClC1=CC(=C(C=C1)NC(=O)C1=CC=C(C=C1)C#N)C(NC1=NC=C(C=C1)Cl)=O.S.IC>>ClC1=CC(=C(C=C1)NC(=O)C1=CC=C(C=C1)C=1N(CCN1)C)C(NC1=NC=C(C=C1)Cl)=O | N[CH2:4][CH2:3][NH:2][CH3:1].[N:5]#[C:6][c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[NH:13][c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]2[C:21](=[O:22])[NH:23][c:24]2[cH:25][cH:26][c:27]([Cl:28])[cH:29][n:30]2)[cH:31][cH:32]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]=[C:6]1[c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[NH:13][c:14]2... | CNCCN.N#Cc1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | CN1CCN=C1c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | null | N1=CC=CC=C1.CO.C(C)(=O)O.C(C)N(CC)CC | Heteroatom Alkylation and Arylation | OtherReaction | c60ad675bbef0aae4bc6f7e7229a0d6b3b6a784179e30b9e067ffd6151067a5c | 4290e5b2bf07838a6d478b39c42778e9467fef0b3ea75c8d873e295925a35d9e | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(C2=NCCN2)cc1 | N-[CH2;D2;+0:1]-[C:2]-[NH;D2;+0:3]-[C;D1;H3:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[N;H0;D3;+0:3]1-[C:2]-[CH2;D2;+0:1]-[N;H0;D2;+0:5]=[C;H0;D3;+0:6]-1-[c:7](:[c:8]):[c:9] | null | [] | null | null | 8 | HOUR | To a solution of the compound of N-{4-chloro-2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}(4-cyanophenyl)carboxamide (683 mg, 1.66 mmol) in anhydrous pyridine (10 ml) and triethyl amine (1 ml) was saturated with hydrogen sulfide gas at 0° C. The mixture was stirred at r.t. overnight. After the evaporated the solvent, the... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Secondary amine | Tertiary amine | null | C1=NCC[NH]1 | C1=NCC[NH]1.c1ccccc1.c1ccccc1.c1ccncc1 | Other | N1=CC=CC=C1.CO.C(C)(=O)O.C(C)N(CC)CC | null | 8 | CNCCN.N#Cc1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1>N1=CC=CC=C1.CO.C(C)(=O)O.C(C)N(CC)CC>CN1CCN=C1c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e59c414aabce448a84c9201254a5dd55 | Cc1ccc([N+](=O)[O-])c(C(=O)O)c1.Nc1ccc(Cl)cn1>>Cc1ccc([N+](=O)[O-])c(C(=O)Nc2ccc(Cl)cn2)c1 | CC=1C=CC(=C(C(=O)O)C1)[N+](=O)[O-].C(C(=O)Cl)(=O)Cl.NC1=NC=C(C=C1)Cl.N1=CC=CC=C1>>ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)C)[N+](=O)[O-] | O[C:10]([c:9]1[c:5]([N+:6](=[O:7])[O-:8])[cH:4][cH:3][c:2]([CH3:1])[cH:20]1)=[O:11].[NH2:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][n:19]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]([C:10](=[O:11])[NH:12][c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][n:19]2)[cH:20]1 | Cc1ccc([N+](=O)[O-])c(C(=O)O)c1.Nc1ccc(Cl)cn1 | Cc1ccc([N+](=O)[O-])c(C(=O)Nc2ccc(Cl)cn2)c1 | null | CN(C=O)C | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccn1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:3](:[c:4]):[c:5] | 92 | [{"value": 92.0, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.9, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 5-methyl-2-nitrobenzoic acid (1 g, 5.52 mmol) in dichloromethane (5 ml) was added oxalyl chloride (0.964 ml, 11.04 mmol) and a few drops of dimethylformamide. The mixture was stirred at r.t. for 2 hrs. After the evaporation of the solvent, the residue was dissolved in dichloromethane (5 ml). 2-amino-5-... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HO- | CN(C=O)C.ClCCl | null | 2 | Cc1ccc([N+](=O)[O-])c(C(=O)O)c1.Nc1ccc(Cl)cn1>CN(C=O)C.ClCCl>Cc1ccc([N+](=O)[O-])c(C(=O)Nc2ccc(Cl)cn2)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9232d5be6aa34d5ebcc88a513c1b7914 | Cc1ccc([N+](=O)[O-])c(C(=O)Nc2ccc(Cl)cn2)c1>>Nc1ccccc1C(=O)Nc1ccccn1.[Cl-] | ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)C)[N+](=O)[O-].[H][H]>>NC1=C(C=CC=C1)C(=O)NC1=NC=CC=C1.[Cl-] | C[c:5]1[cH:4][cH:3][c:2]([N+:1](=O)[O-])[c:7]([C:8](=[O:9])[NH:10][c:11]2[cH:12][cH:13][c:14]([Cl:17])[cH:15][n:16]2)[cH:6]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][n:16]1.[Cl-:17] | Cc1ccc([N+](=O)[O-])c(C(=O)Nc2ccc(Cl)cn2)c1 | Nc1ccccc1C(=O)Nc1ccccn1.[Cl-] | null | [Pt] | CO | Functional Group Interconversion | OtherReaction | 7335ad64e689ca4e08d92da67da5a4ba3d7b1ae27a9bb5d9a29f9de23a6b4f9a | f3a5ba2ad2c4d7897d16c1f6f55c603d6dd39035ce4ed56632c5b924cbe6ba83 | O=C(Nc1ccccn1)c1ccccc1 | C-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[N+;H0;D3:5](=O)-[O-]):[c:6](-[C:7](=[O;D1;H0:8])-[#7:9]-[c:10]2:[#7;a:11]:[c:12]:[c;H0;D3;+0:13](-[Cl;H0;D1;+0:14]):[c:15]:[c:16]:2):[c:17]:1>>[Cl-;H0;D0:14].[NH2;D1;+0:5]-[c:4]1:[c:3]:[c:2]:[cH;D2;+0:1]:[c:17]:[c:6]:1-[C:7](=[O;D1;H0:8])-[#7:9]-[c:10]1:[#7;a:11]:[c:12]:[cH;D2;+0:1... | null | [] | null | null | null | null | To a solution of the compound of N-(5-chloro(2-pyridyl))(5-methyl-2-nitrophenyl)carboxamide (1.48 g, 5.1 mmol) in methanol (10 ml) was added 5% Pt/C (1.48 g, 0.19 mmol). The mixture was applied hydrogen balloon at r.t. for 2 hrs. After the filtration by Celite, the filtrate was concentrated to give (2-aminophenyl)-N-(2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Nitro group | Primary amine | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | Other | [Pt].CO | null | null | Cc1ccc([N+](=O)[O-])c(C(=O)Nc2ccc(Cl)cn2)c1>[Pt].CO>Nc1ccccc1C(=O)Nc1ccccn1.[Cl-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2bbf6d4c24094021b4487360c5a0e84d | COc1cc(C(=O)O)c([N+](=O)[O-])c(OC)c1OC.Nc1ccc(Br)cn1>>COc1cc(C(=O)Nc2ccc(Br)cn2)c([N+](=O)[O-])c(OC)c1OC | COC=1C(=C(C(=O)O)C=C(C1OC)OC)[N+](=O)[O-].C(C(=O)Cl)(=O)Cl.NC1=NC=C(C=C1)Br.N1=CC=CC=C1>>BrC=1C=CC(=NC1)NC(=O)C1=C(C(=C(C(=C1)OC)OC)OC)[N+](=O)[O-] | O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH3:25])[c:20]([O:21][CH3:22])[c:16]1[N+:17](=[O:18])[O-:19])=[O:7].[NH2:8][c:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][n:15]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][n:15]2)[c:16]([N+:17](=[O:18])[O-:19])[c:20]([O:21... | COc1cc(C(=O)O)c([N+](=O)[O-])c(OC)c1OC.Nc1ccc(Br)cn1 | COc1cc(C(=O)Nc2ccc(Br)cn2)c([N+](=O)[O-])c(OC)c1OC | null | CN(C=O)C | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccn1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:3](:[c:4]):[c:5] | 98.3 | [{"value": 98.0, "product": "BrC=1C=CC(=NC1)NC(=O)C1=C(C(=C(C(=C1)OC)OC)OC)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.3, "product": "BrC=1C=CC(=NC1)NC(=O)C1=C(C(=C(C(=C1)OC)OC)OC)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3,4,5-trimethoxy-2-nitrobenzoic acid (0.5 g, 1.95 mmol) in dichloromethane (5 ml) was added oxalyl chloride (0.34 ml, 3.9 mmol) and a few drops of dimethylformamide. The mixture was stirred at r.t. for 2 hrs. After the evaporation of the solvent, the residue was dissolved in dichloromethane (5 ml). 2-a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1 | HO- | CN(C=O)C.ClCCl | null | 2 | COc1cc(C(=O)O)c([N+](=O)[O-])c(OC)c1OC.Nc1ccc(Br)cn1>CN(C=O)C.ClCCl>COc1cc(C(=O)Nc2ccc(Br)cn2)c([N+](=O)[O-])c(OC)c1OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-5d027d64052b488a8ef5f9422039c307 | COc1cc(C(=O)Nc2ccc(Br)cn2)c([N+](=O)[O-])c(OC)c1OC>>COc1cc(C(=O)Nc2ccc(Br)cn2)c(N)c(OC)c1OC | BrC=1C=CC(=NC1)NC(=O)C1=C(C(=C(C(=C1)OC)OC)OC)[N+](=O)[O-]>>NC1=C(C=C(C(=C1OC)OC)OC)C(=O)NC1=NC=C(C=C1)Br | O=[N+:17]([O-])[c:16]1[c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][n:15]2)[cH:4][c:3]([O:2][CH3:1])[c:21]([O:22][CH3:23])[c:18]1[O:19][CH3:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][n:15]2)[c:16]([NH2:17])[c:18]([O:19][CH3:20])[c:21]1[O:22][CH... | COc1cc(C(=O)Nc2ccc(Br)cn2)c([N+](=O)[O-])c(OC)c1OC | COc1cc(C(=O)Nc2ccc(Br)cn2)c(N)c(OC)c1OC | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(Nc1ccccn1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]-[C:5](-[#7:6])=[O;D1;H0:7]>>[#7:6]-[C:5](=[O;D1;H0:7])-[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 77.7 | [{"value": 77.0, "product": "NC1=C(C=C(C(=C1OC)OC)OC)C(=O)NC1=NC=C(C=C1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.7, "product": "NC1=C(C=C(C(=C1OC)OC)OC)C(=O)NC1=NC=C(C=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of the compound of N-(5-bromo(2-pyridyl))(3,4,5-trimethoxy-2-nitrophenyl)carboxamide (790 mg, 1.92 mmol) in ethyl acetate (5 ml) was added tin chloride (II) hydrate (1.73 g, 7.67 mmol). The mixture was stirred under reflux condition for 2 hrs. After filtered by Celite, the filtrate was added 1N sodium hyd... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccncc1 | Other | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)(=O)OCC | null | null | COc1cc(C(=O)Nc2ccc(Br)cn2)c([N+](=O)[O-])c(OC)c1OC>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)(=O)OCC>COc1cc(C(=O)Nc2ccc(Br)cn2)c(N)c(OC)c1OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7769d72acc204e3c94f7a4faf46f2404 | CNCCN.COc1cc(C(=O)Nc2ccc(Br)cn2)c(NC(=O)c2ccc(C#N)cc2)c(OC)c1OC>>COc1cc(C(=O)Nc2ccc(Br)cn2)c(NC(=O)c2ccc(C3=NCCN3C)cc2)c(OC)c1OC | BrC=1C=CC(=NC1)NC(=O)C1=CC(=C(C(=C1NC(=O)C1=CC=C(C=C1)C#N)OC)OC)OC.Cl.CNCCN>>BrC=1C=CC(=NC1)NC(=O)C1=CC(=C(C(=C1NC(=O)C1=CC=C(C=C1)C=1N(CCN1)C)OC)OC)OC | [NH2:25][CH2:26][CH2:27][NH:28][CH3:29].N#[C:24][c:23]1[cH:22][cH:21][c:20]([C:18]([NH:17][c:16]2[c:5]([C:6](=[O:7])[NH:8][c:9]3[cH:10][cH:11][c:12]([Br:13])[cH:14][n:15]3)[cH:4][c:3]([O:2][CH3:1])[c:35]([O:36][CH3:37])[c:32]2[O:33][CH3:34])=[O:19])[cH:31][cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][c:9]... | CNCCN.COc1cc(C(=O)Nc2ccc(Br)cn2)c(NC(=O)c2ccc(C#N)cc2)c(OC)c1OC | COc1cc(C(=O)Nc2ccc(Br)cn2)c(NC(=O)c2ccc(C3=NCCN3C)cc2)c(OC)c1OC | null | null | CO.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | c60ad675bbef0aae4bc6f7e7229a0d6b3b6a784179e30b9e067ffd6151067a5c | 4290e5b2bf07838a6d478b39c42778e9467fef0b3ea75c8d873e295925a35d9e | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(C2=NCCN2)cc1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C:7]-[C:8]-[NH2;D1;+0:9]>>[C;D1;H3:5]-[N;H0;D3;+0:6]1-[C:7]-[C:8]-[N;H0;D2;+0:9]=[C;H0;D3;+0:1]-1-[c:2](:[c:3]):[c:4] | 32 | [{"value": 32.0, "product": "BrC=1C=CC(=NC1)NC(=O)C1=CC(=C(C(=C1NC(=O)C1=CC=C(C=C1)C=1N(CCN1)C)OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.7, "product": "BrC=1C=CC(=NC1)NC(=O)C1=CC(=C(C(=C1NC(=O)C1=CC=C(C=C1)C=1N(CCN1)C)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of the compound of N-{6-[N-(5-bromo(2-pyridyl))carbamoyl]-2,3,4-trimethoxyphenyl}(4-cyanophenyl)carboxamide (680 mg, 1.33 mmol) in anhydrous methanol (5 ml) and ethyl acetate (10 ml) was saturated with hydrogen chloride gas at 0° C. The mixture was stirred at r.t. overnight. After the evaporated the solve... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Secondary amine | Tertiary amine | null | C1=NCC[NH]1 | c1ccccc1.c1ccncc1.c1ccccc1.C1=NCC[NH]1 | Other | CO.C(C)(=O)OCC | null | 8 | CNCCN.COc1cc(C(=O)Nc2ccc(Br)cn2)c(NC(=O)c2ccc(C#N)cc2)c(OC)c1OC>CO.C(C)(=O)OCC>COc1cc(C(=O)Nc2ccc(Br)cn2)c(NC(=O)c2ccc(C3=NCCN3C)cc2)c(OC)c1OC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1e221f4018b74cbe910c2e2fc6fd7adf | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1>>NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | C(C)(C)(C)NS(=O)(=O)C1=C(C=CC=C1)C1=CC=C(C=C1)C(=O)NC1=C(C=C(C=C1)Cl)C(=O)NC1=NC=C(C=C1)Cl>>ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)Cl)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)S(N)(=O)=O | CC(C)(C)[NH:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[NH:17][c:18]2[cH:19][cH:20][c:21]([Cl:22])[cH:23][c:24]2[C:25](=[O:26])[NH:27][c:28]2[cH:29][cH:30][c:31]([Cl:32])[cH:33][n:34]2)[cH:35][cH:36]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9... | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | null | FC(C(=O)O)(F)F | Deprotection | Tert-butyl deprotection of amine | f7e1da1b4c254f1e6d5afbf8cb56733a4fabd145b80e971e3b7e31007de9e7d6 | 278d0fb11b582c058ac903379d7fbe11ab8c395937a204965031cf0c344845a9 | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(-c2ccccc2)cc1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5]>>[NH2;D1;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5] | 25 | [{"value": 25.0, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)Cl)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)S(N)(=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | The mixture of the compound of (2-{[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]carbonylamino}-5-chlorophenyl)-N-(5-chloro(2-pyridyl))carboxamide example 12 (0.5 mmol) in trifluoroacetic acid (5 ml) was stirred at r.t. for 5 hrs. After the evaporation of solvent, the crude residue was purified by RP-HPLC to give N-... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccncc1 | Other | FC(C(=O)O)(F)F | null | 5 | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1>FC(C(=O)O)(F)F>NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6a9c648c8a92401d884fc1d049821c8d | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>>N=C(N)c1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | S.ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C#N.N1=CC=CC=C1.CI>>ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C(=N)N | [N:1]#[C:2][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][cH:12][c:13]([C:14](=[O:15])[NH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[C:23](=[O:24])[NH:25][c:26]2[cH:27][cH:28][c:29]([Cl:30])[cH:31][n:32]2)[cH:33][cH:34]1>>[NH:1]=[C:2]([NH2:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1-[c:10]1[cH:11][cH:12][c:13]([C:1... | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | N=C(N)c1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | null | C(C)(=O)O.CO.CC(=O)C.CCN(CC)CC | Functional Group Addition | OtherReaction | b3aaef1538bea73aa85740ccbb089c1b6ca4b164a10fd32235acb6c78d1de6d9 | d1a81d2cc57b1a744f94f80261b8629cf532e8b73012860cc8db4db5903fee1a | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(-c2ccccc2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[N;D1;H2:6]-[C;H0;D3;+0:2](=[NH;D1;+0:1])-[c:3](:[c:4]):[c:5] | 15 | [{"value": 15.0, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C(=N)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | A stream of H2S (g) was bubbled through a 0° C. solution of N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}[4-(2-cyanophenyl)phenyl]carboxamide (100 mg, 0.22 mmol, 1.0 equiv.) in 9 mL pyridine and 1 mL NEt3 until saturation. The mixture was stirred at rt for 1 day and evaporated. The resulting residue was treated with M... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccncc1 | Other | C(C)(=O)O.CO.CC(=O)C.CCN(CC)CC | null | 24 | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>C(C)(=O)O.CO.CC(=O)C.CCN(CC)CC>N=C(N)c1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d4ccddbfae804ede959e9ad19a2553fb | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1.NO>>O=C(Nc1ccccc1C(=O)Nc1ccc(Cl)cn1)c1ccc(-c2ccccc2C=NNO)cc1 | ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C#N.Cl.ON.C(C)N(CC)CC>>ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C=NNO | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][n:19]1)[c:20]1[cH:21][cH:22][c:23](-[c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]2[C:30]#[N:31])[cH:34][cH:35]1.[NH2:32][OH:33]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12... | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1.NO | O=C(Nc1ccccc1C(=O)Nc1ccc(Cl)cn1)c1ccc(-c2ccccc2C=NNO)cc1 | null | null | C(C)O | Miscellaneous | OtherReaction | 5ebc8ae9c43671ddb0100b0cbc1ec0c40d1e187e38be7171f745b68f0dc6a2a1 | 58f66636c1d89ede1b1e759542791677a2888499f20f253f7f8ee20c2e377b3e | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(-c2ccccc2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[O;D1;H1:7]>>[O;D1;H1:7]-[NH;D2;+0:6]-[N;H0;D2;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | 27.5 | [{"value": 27.5, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C=NNO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.4, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C=NNO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | DAY | A mixture of N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}[4-(2-cyanophenyl)phenyl]carboxamide (14 mg, 0.03 mmol, 1.0 equiv.), hydroxyamine hydrochloride (6.25 mg, 0.09 mmol, 3.0 equiv.) and triethyl amine (0.03 mL, 0.3 mmol, 10.0 equiv.) in ethanol (3 mL) was stirred at rt for 6 days, concentrated and HPLC (C18 rever... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Hydrazone | null | null | c1ccccc1.c1ccncc1.c1ccccc1.c1ccccc1 | null | C(C)O | null | 144 | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1.NO>C(C)O>O=C(Nc1ccccc1C(=O)Nc1ccc(Cl)cn1)c1ccc(-c2ccccc2C=NNO)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-df56acc56a7b43ff82539f9c599b7997 | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>>NCc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)C#N.[BH4-].[Na+]>>NCC1=C(C=CC=C1)C1=CC=C(C=C1)C(=O)NC1=C(C=CC=C1)C(NC1=NC=C(C=C1)Cl)=O | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[C:22](=[O:23])[NH:24][c:25]2[cH:26][cH:27][c:28]([Cl:29])[cH:30][n:31]2)[cH:32][cH:33]1>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14... | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | NCc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | [Co](Cl)Cl | CN(C)C=O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(-c2ccccc2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 43.1 | [{"value": 43.0, "product": "NCC1=C(C=CC=C1)C1=CC=C(C=C1)C(=O)NC1=C(C=CC=C1)C(NC1=NC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.1, "product": "NCC1=C(C=CC=C1)C1=CC=C(C=C1)C(=O)NC1=C(C=CC=C1)C(NC1=NC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | A mixture of N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}[4-(2-cyanophenyl)phenyl]carboxamide (200 mg, 0.442 mmol, 1.0 equiv.), cobalt chloride (86 mg, 0.664 mmol, 1.5 equiv.) and sodium borohydride (50 mg, 1.33 mmol, 3.0 equiv.) in DMF (15 mL) was stirred at 0° C. to rt for 3 days. The reaction was quenched with ice... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccncc1 | null | [Co](Cl)Cl.CN(C)C=O | null | 72 | N#Cc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>[Co](Cl)Cl.CN(C)C=O>NCc1ccccc1-c1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-25ac70975bee4da599786cc6820b43b6 | N#Cc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>>NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)C#N.[BH4-].[Na+]>>NCC1=CC=C(C=C1)C(=O)NC1=C(C=CC=C1)C(NC1=NC=C(C=C1)Cl)=O | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16](=[O:17])[NH:18][c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][n:25]2)[cH:26][cH:27]1>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16](=[O:17])[NH:18][c:19]2[cH:20... | N#Cc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | [Co](Cl)Cl | CN(C)C=O | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 32.3 | [{"value": 30.0, "product": "NCC1=CC=C(C=C1)C(=O)NC1=C(C=CC=C1)C(NC1=NC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.3, "product": "NCC1=CC=C(C=C1)C(=O)NC1=C(C=CC=C1)C(NC1=NC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | A mixture of N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}(4-cyanophenyl)carboxamide (1 g, 2.6 mmol, 1.0 equiv.), cobalt chloride (0.5 g, 3.85 mmol, 1.5 equiv.) and sodium borohydride (0.295 g, 7.8 mmol, 3.0 equiv.) in DMF (20 mL) was stirred at 0° C. to rt for 2.5 hr. The reaction was quenched with ice cubes, diluted... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccncc1 | null | [Co](Cl)Cl.CN(C)C=O | null | 2.5 | N#Cc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>[Co](Cl)Cl.CN(C)C=O>NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-adc2d14070de4043a6664ee9a6e9deaf | CSC1=NCCN1.NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>>O=C(Nc1ccccc1C(=O)Nc1ccc(Cl)cn1)c1ccc(CNC2=NCCN2)cc1 | NCC1=CC=C(C=C1)C(=O)NC1=C(C=CC=C1)C(NC1=NC=C(C=C1)Cl)=O.I.CSC=1NCCN1.C(C)N(CC)CC>>ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)CNC=1NCCN1 | CS[C:26]1=[N:27][CH2:28][CH2:29][NH:30]1.[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][n:19]1)[c:20]1[cH:21][cH:22][c:23]([CH2:24][NH2:25])[cH:31][cH:32]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14]... | CSC1=NCCN1.NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | O=C(Nc1ccccc1C(=O)Nc1ccc(Cl)cn1)c1ccc(CNC2=NCCN2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | b8b2c7cb02682d6c06684e6c7b2dfb49c6d9023dd6b43e4d41769a82c503b02f | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(CNC2=NCCN2)cc1 | C-S-[C;H0;D3;+0:1]1=[#7:2]-[C:3]-[C:4]-[#7:5]-1.[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:8]-[C:7]-[NH;D2;+0:6]-[C;H0;D3;+0:1]1=[#7:2]-[C:3]-[C:4]-[#7:5]-1 | 15 | [{"value": 15.0, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)CNC=1NCCN1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.3, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)CNC=1NCCN1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of [4-(aminomethyl)phenyl]-N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}carboxamide (80 mg, 0.21 mmol), 2-methylthio-2-imidazoline hydriodide (77 mg, 0.315 mmol, 1.5 equiv.) and triethyl amine (0.5 mL) in 1 mL DMF was stirred at room temperature overnight, concentrated to dryness and HPLC (C18 reversed phase... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | C1=NCCN1 | C1=NCCN1 | c1ccccc1.c1ccncc1.c1ccccc1.C1=NCCN1 | Other | CN(C)C=O | null | 8 | CSC1=NCCN1.NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>CN(C)C=O>O=C(Nc1ccccc1C(=O)Nc1ccc(Cl)cn1)c1ccc(CNC2=NCCN2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-abaf463b08694e7e97c7286f7583efbb | CSC1=NCCN1C.NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>>CN1CCN=C1NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | NCC1=CC=C(C=C1)C(=O)NC1=C(C=CC=C1)C(NC1=NC=C(C=C1)Cl)=O.CN1C(=NCC1)SC.CCN(CC)CC>>ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)CNC=1N(CCN1)C | CS[C:6]1=[N:5][CH2:4][CH2:3][N:2]1[CH3:1].[NH2:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[NH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[C:22](=[O:23])[NH:24][c:25]2[cH:26][cH:27][c:28]([Cl:29])[cH:30][n:31]2)[cH:32][cH:33]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]=[C:6]1[NH:7][CH2:8][c:9]1[cH:10][cH:11][c:12]([C:1... | CSC1=NCCN1C.NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | CN1CCN=C1NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 3d9229dd690869c9ac61e6b6820af19abd0e765828a31068efa43748fe7d0ebd | 88e0224d19b2dce8f9987d52554afb32090d36ff7ee19e89dc5bf66d30974ec4 | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccc(CNC2=NCCN2)cc1 | C-S-[C;H0;D3;+0:1]1=[#7:2]-[C:3]-[C:4]-[#7:5]-1-[C;D1;H3:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[C;D1;H3:6]-[#7:5]1-[C:4]-[C:3]-[#7:2]=[C;H0;D3;+0:1]-1-[NH;D2;+0:7]-[C:8]-[c:9] | 65 | [{"value": 65.0, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)CNC=1N(CCN1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.6, "product": "ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC=C1)NC(=O)C1=CC=C(C=C1)CNC=1N(CCN1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 8 | HOUR | A mixture of [4-(aminomethyl)phenyl]-N-{2-[N-(5-chloro(2-pyridyl))carbamoyl]phenyl}carboxamide (74 mg, 0.195 mmol), 1-methyl-2-methylthio-2-imidazoline (25 mg, 0.195 mmol), NEt3 (2 mL) and pyridine (5 mL) was stirred at 80° C. overnight, concentrated and HPLC (C18 reversed phase) eluting with 0.1% TFA in H2O/CH3CN gave... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Monosulfide | Secondary amine | C1=NCC[NH]1 | C1=NCC[NH]1 | C1=NCC[NH]1.c1ccccc1.c1ccccc1.c1ccncc1 | Other | N1=CC=CC=C1 | 80 | 8 | CSC1=NCCN1C.NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1>N1=CC=CC=C1>CN1CCN=C1NCc1ccc(C(=O)Nc2ccccc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b7fdc228ba5a4a11b5ad77c59bddf049 | Nc1ccc(Br)cn1.O=C(O)c1cc(F)ccc1[N+](=O)[O-]>>O=C(Nc1ccc(Br)cn1)c1cc(F)ccc1[N+](=O)[O-] | FC=1C=CC(=C(C(=O)O)C1)[N+](=O)[O-].NC1=NC=C(C=C1)Br.P(=O)(Cl)(Cl)Cl>>BrC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)F)[N+](=O)[O-] | [NH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][n:10]1.O[C:2](=[O:1])[c:11]1[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]1[N+:18](=[O:19])[O-:20]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][n:10]1)[c:11]1[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]1[N+:18](=[O:19])[O-:20] | Nc1ccc(Br)cn1.O=C(O)c1cc(F)ccc1[N+](=O)[O-] | O=C(Nc1ccc(Br)cn1)c1cc(F)ccc1[N+](=O)[O-] | null | null | N1=CC=CC=C1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccn1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[#7;a:9]:[c:10])-[c:3](:[c:4]):[c:5] | 68.1 | [{"value": 68.0, "product": "BrC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)F)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.1, "product": "BrC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)F)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-fluoro-2-nitrobenzoic acid (10.0 g, 54 mmol, 1.0 equiv), 2-amino-5-bromopyridine (12.2 g, 1.3 equiv), in 80 mL of pyridine was treated with phosphorous oxychloride (25.3 g, 3.0 equiv) for 30 min. The volatile was evaporated and the residue was redissolved into EtOAc, washed with 1N HCl, saturated aqueou... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1 | HO- | N1=CC=CC=C1 | null | null | Nc1ccc(Br)cn1.O=C(O)c1cc(F)ccc1[N+](=O)[O-]>N1=CC=CC=C1>O=C(Nc1ccc(Br)cn1)c1cc(F)ccc1[N+](=O)[O-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-934bb560f06943beac5ef9af786f1c83 | COc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1.NO>>COc1ccc(NC(=O)c2ccc(C(N)=NO)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1 | ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)OC)NC(=O)C1=CC=C(C=C1)C#N.Cl.ON.CCN(CC)CC>>NC(C1=CC=C(C=C1)C(=O)NC1=C(C=C(C=C1)OC)C(=O)NC1=NC=C(C=C1)Cl)=NO | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([C:14]#[N:15])[cH:18][cH:19]2)[c:20]([C:21](=[O:22])[NH:23][c:24]2[cH:25][cH:26][c:27]([Cl:28])[cH:29][n:30]2)[cH:31]1.[NH2:16][OH:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([C:14]([NH2:15])=[... | COc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1.NO | COc1ccc(NC(=O)c2ccc(C(N)=NO)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1 | null | null | CCO | Heteroatom Alkylation and Arylation | Amidoxime from nitrile and hydroxylamine | 5f2123b5002b6939ec57e4f55921371a47c78c3ff253c724d87881638fedcd4f | ad3f1127a4d99506976df608684863fb1e08b35faede2d4e31cf4ca96393cd2e | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[O;D1;H1:7]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[N;H0;D2;+0:6]-[O;D1;H1:7])-[c:3](:[c:4]):[c:5] | null | [] | 60 | CELSIUS | 8 | HOUR | To a suspension of compound N-(5-chloro(2-pyridyl)){2-[(4-cyanophenyl)carbonylamino]-5-methoxyphenyl}carboxamide (150 mg) in EtOH (10 mL) was added hydroxyamine hydrochloride (80 mg) and Et3N (200 μL). The mixture was stirred at 60° C. overnight and the reaction was complete. The solvent was evaporated and the crude ma... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Primary amine.Oxime | null | null | c1ccccc1.c1ccccc1.c1ccncc1 | null | CCO | 60 | 8 | COc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1.NO>CCO>COc1ccc(NC(=O)c2ccc(C(N)=NO)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0cea701aedfa45818392ccfd94d67ffe | COc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1>>N#Cc1ccc(C(=O)Nc2ccc(O)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | ClC=1C=CC(=NC1)NC(=O)C1=C(C=CC(=C1)OC)NC(=O)C1=CC=C(C=C1)C#N.B(Br)(Br)Br>>ClC=1C=CC(=NC1)NC(=O)C1=CC(=CC=C1NC(=O)C1=CC=C(C=C1)C#N)O | C[O:14][c:13]1[cH:12][cH:11][c:10]([NH:9][C:7]([c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:28][cH:27]2)=[O:8])[c:16]([C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][c:23]([Cl:24])[cH:25][n:26]2)[cH:15]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([OH:14])[cH:15][c:16]2[C:17](=[O:18])[NH:1... | COc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1 | N#Cc1ccc(C(=O)Nc2ccc(O)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 90 | [{"value": 90.0, "product": "ClC=1C=CC(=NC1)NC(=O)C1=CC(=CC=C1NC(=O)C1=CC=C(C=C1)C#N)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | To a suspension of compound N-(5-chloro(2-pyridyl)){2-[(4-cyanophenyl)-carbonylamino]-5-methoxyphenyl}carboxamide (500 mg, 1.2 mmol) in DCM (100 mL) at −78° C. was added BBr3 (2 mL). The mixture was stirred at ambient temperatures for 72 hours. The solid was collected by filtration and was washed by DCM and water, drie... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1.c1ccncc1 | Other | C(Cl)Cl | null | 72 | COc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1>C(Cl)Cl>N#Cc1ccc(C(=O)Nc2ccc(O)cc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-66e3e8667dab4935b11f19d6ae8554e3 | CCOC(=O)CBr.N#Cc1ccc(C(=O)Nc2ccc(O)cc2C(=O)Nc2ccc(Cl)cn2)cc1>>CCOC(=O)COc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1 | ClC=1C=CC(=NC1)NC(=O)C1=CC(=CC=C1NC(=O)C1=CC=C(C=C1)C#N)O.C(=O)([O-])[O-].[Cs+].[Cs+].BrCC(=O)OCC>>ClC=1C=CC(=NC1)NC(=O)C=1C=C(OCC(=O)OCC)C=CC1NC(=O)C1=CC=C(C=C1)C#N | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[c:15]2[cH:16][cH:17][c:18]([C:19]#[N:20])[cH:21][cH:22]2)[c:23]([C:24](=[O:25])[NH:26][c:27]2[cH:28][cH:29][c:30]([Cl:31])[cH:32][n:33]2)[cH:34]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[cH:9][cH:10][c:11]([NH:12... | CCOC(=O)CBr.N#Cc1ccc(C(=O)Nc2ccc(O)cc2C(=O)Nc2ccc(Cl)cn2)cc1 | CCOC(=O)COc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1 | null | null | CCOC(=O)C.O.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 112.4 | [{"value": 112.4, "product": "ClC=1C=CC(=NC1)NC(=O)C=1C=C(OCC(=O)OCC)C=CC1NC(=O)C1=CC=C(C=C1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a mixture of compound N-(5-chloro(2-pyridyl)){6-[(4-cyanophenyl)-carbonylamino]-3-hydroxyphenyl}carboxamide (50 mg, 0.13 mmol) and Cs2CO3 (83 mg, 0.25 mmol) in DMF (1 mL) at room temperature was added ethyl bromoacetate (15 μL, 0.13 mmol). The mixture was stirred for 1 hour before diluted with EtOAc (20 mL) and wate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.c1ccccc1.c1ccncc1 | HBr | CCOC(=O)C.O.CN(C)C=O | null | 1 | CCOC(=O)CBr.N#Cc1ccc(C(=O)Nc2ccc(O)cc2C(=O)Nc2ccc(Cl)cn2)cc1>CCOC(=O)C.O.CN(C)C=O>CCOC(=O)COc1ccc(NC(=O)c2ccc(C#N)cc2)c(C(=O)Nc2ccc(Cl)cn2)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-77362edf322045e8a72f238e86be1f41 | Nc1ccc(Cl)cn1.O=c1[nH]c2ccc(Cl)cc2c(=O)o1>>Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 | ClC1=CC=C2C(C(=O)OC(N2)=O)=C1.NC1=NC=C(C=C1)Cl.C[Si](C)(C)[N-][Si](C)(C)C.[K+].C1(=CC=CC=C1)C>>NC1=C(C=C(C=C1)Cl)C(=O)NC1=NC=C(C=C1)Cl | [NH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][n:18]1.O=c1o[c:9](=[O:10])[c:8]2[c:2]([nH:1]1)[cH:3][cH:4][c:5]([Cl:6])[cH:7]2>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][n:18]1 | Nc1ccc(Cl)cn1.O=c1[nH]c2ccc(Cl)cc2c(=O)o1 | Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 | null | null | O1CCCC1 | Acylation | OtherReaction | b4c245015e48b9b60756b62e3f8985928af86452315d98417a25faace320d9ae | b609a70ccab739990a9ccc4ea2adcc77011bcd0c07154489a12420f7c0e7382e | O=C(Nc1ccccn1)c1ccccc1 | O=c1:[nH;D2;+0:1]:[c:2](:[c:3]):[c:4](:[c:5]):[c;H0;D3;+0:6](=[O;D1;H0:7]):o:1.[NH2;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]):[c:5] | 99 | [{"value": 99.0, "product": "NC1=C(C=C(C=C1)Cl)C(=O)NC1=NC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.6, "product": "NC1=C(C=C(C=C1)Cl)C(=O)NC1=NC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 0.5 | HOUR | To a solution of 2-amino-5-chloropyridine (787 mg, 6.1 mmol) in tetrahydrofuran (5 ml) was added 0.5M potassium bis(trimethylsilyl)amide in toluene (20 ml, 10.1 mmol) dropwise at −78° C. After stirred for additional 0.5 hr at −78° C., the mixture was added 5-chloroisatoic anhydride (1 g, 5.1 mmol) at −78° C. The mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide.Primary amine | c1ccc2ncocc2c1 | c1ccccc1 | c1ccccc1.c1ccncc1 | Other | O1CCCC1 | -78 | 0.5 | Nc1ccc(Cl)cn1.O=c1[nH]c2ccc(Cl)cc2c(=O)o1>O1CCCC1>Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-78423b0ee2724e0eb24f94e6674e11e0 | N#Cc1ccc(C(=O)O)c(F)c1.Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1>>N#Cc1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)c(F)c1 | FC1=C(C(=O)O)C=CC(=C1)C#N.NC1=C(C=C(C=C1)Cl)C(=O)NC1=NC=C(C=C1)Cl.N1=CC=CC=C1>>ClC1=CC(=C(C=C1)NC(=O)C1=C(C=C(C=C1)C#N)F)C(NC1=NC=C(C=C1)Cl)=O | O[C:7]([c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:29][c:27]1[F:28])=[O:8].[NH2:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]1[C:17](=[O:18])[NH:19][c:20]1[cH:21][cH:22][c:23]([Cl:24])[cH:25][n:26]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[NH:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]2[C:17](=[O:18]... | N#Cc1ccc(C(=O)O)c(F)c1.Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1 | N#Cc1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)c(F)c1 | null | null | ClCCl.S(=O)(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccccc1C(=O)Nc1ccccn1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH2;D1;+0:11]):[c:12]>>[#7:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:12] | 111.3 | [{"value": 78.0, "product": "ClC1=CC(=C(C=C1)NC(=O)C1=C(C=C(C=C1)C#N)F)C(NC1=NC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 111.3, "product": "ClC1=CC(=C(C=C1)NC(=O)C1=C(C=C(C=C1)C#N)F)C(NC1=NC=C(C=C1)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 2-fluoro-4-cyanobenzoic acid (1 g, 6.06 mmol) in thionyl chloride (5 ml) was refluxed for 2 hr. After concentration, the residue was dissolved in dichloromethane (5 ml). And a solution of the compound of (2-amino-5-chlorophenyl)-N-(5-chloro(2-pyridyl))carboxamide (1.2 g, 4.25 mmol) in dichloromethane (10 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccncc1 | HO- | ClCCl.S(=O)(Cl)Cl | null | 8 | N#Cc1ccc(C(=O)O)c(F)c1.Nc1ccc(Cl)cc1C(=O)Nc1ccc(Cl)cn1>ClCCl.S(=O)(Cl)Cl>N#Cc1ccc(C(=O)Nc2ccc(Cl)cc2C(=O)Nc2ccc(Cl)cn2)c(F)c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-81f661704e87442ca5d59fd306477d4f | COC(=O)c1sccc1N.N#Cc1ccc(C(=O)Cl)cc1>>COC(=O)c1sccc1NC(=O)c1ccc(C#N)cc1 | C(#N)C1=CC=C(C(=O)Cl)C=C1.NC1=C(SC=C1)C(=O)OC.C(C)N(CC)CC>>C(#N)C1=CC=C(C=C1)C(=O)NC1=C(SC=C1)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][cH:7][cH:8][c:9]1[NH2:10].Cl[C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][cH:7][cH:8][c:9]1[NH:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([C:17]#[N:18])[cH:19][cH:20]1 | COC(=O)c1sccc1N.N#Cc1ccc(C(=O)Cl)cc1 | COC(=O)c1sccc1NC(=O)c1ccc(C#N)cc1 | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccsc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1-[NH2;D1;+0:14]>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1-[NH;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 91 | [{"value": 91.0, "product": "C(#N)C1=CC=C(C=C1)C(=O)NC1=C(SC=C1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.5, "product": "C(#N)C1=CC=C(C=C1)C(=O)NC1=C(SC=C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A mixture of 4-cyanobenzoyl chloride (1.0500 g, 6.4 mmol), methyl 3-aminothiophenecarboxylate (1.0000 g, 6.4 mmol), and triethylamine (1 mL, 7.0 mmol) in dichloromethane was stirred at room temperature for 18 hours. The mixture was poured into a separatory funnel and washed by 1 N HCl. The organic layers were combined,... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccsc1.c1ccccc1 | HCl | ClCCl | null | 18 | COC(=O)c1sccc1N.N#Cc1ccc(C(=O)Cl)cc1>ClCCl>COC(=O)c1sccc1NC(=O)c1ccc(C#N)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c06c18e12e844b22ab1552843c34d3b0 | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Cl)cc1.Nc1ccsc1C(=O)Nc1cc(Cl)ccn1>>NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccsc2C(=O)Nc2ccc(Cl)cn2)cc1 | C(C)(C)(C)NS(=O)(=O)C1=C(C=CC=C1)C1=CC=C(C(=O)Cl)C=C1.NC1=C(SC=C1)C(=O)NC1=NC=CC(=C1)Cl.N1=CC=CC=C1.ClCCl.ClCCl>>ClC=1C=CC(=NC1)NC(=O)C=1SC=CC1NC(=O)C1=CC=C(C=C1)C1=C(C=CC=C1)S(N)(=O)=O | CC(C)(C)[NH:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:11]1[cH:12][cH:13][c:14]([C:15](Cl)=[O:16])[cH:33][cH:34]1.[NH2:17][c:18]1[cH:19][cH:20][s:21][c:22]1[C:23](=[O:24])[NH:25][c:26]1[cH:27][c:29]([Cl:30])[cH:28][cH:31][n:32]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1-[c:... | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Cl)cc1.Nc1ccsc1C(=O)Nc1cc(Cl)ccn1 | NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccsc2C(=O)Nc2ccc(Cl)cn2)cc1 | null | null | null | Acylation | OtherReaction | 62b79e27f73e217708be777171a101fdbc2ae1e8bb0a9b0fa120e1de8f226bfb | 5bed3f68e2efbf0da9a9b01be7a80f098581b44c7deee6d8009e459217c3f840 | O=C(Nc1ccsc1C(=O)Nc1ccccn1)c1ccc(-c2ccccc2)cc1 | C-C(-C)(-C)-[NH;D2;+0:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[c:5].Cl-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[Cl;D1;H0:11]-[c;H0;D3;+0:12]1:[cH;D2;+0:13]:[c:14](-[#7:15]-[C:16](=[O;D1;H0:17])-[c:18]2:[#16;a:19]:[c:20]:[c:21]:[c:22]:2-[NH2;D1;+0:23]):[#7;a:24]:[cH;D2;+0:25]:[cH;D2;+0:26]:1>>[Cl;D1;H0:11]-[c;H... | null | [] | null | null | null | null | A solution of 4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)benzoyl chloride (1 equiv), 3-amino-2-(4-chloro-2-pyridinyl)aminocarbonyl thiophene (1 equiv), pyridine (5 equiv) in dichloromethane was stirred at rt overnight. The mixture was diluted with dichloromethane, washed with water, dried over Na2SO4, filtered and evapor... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Sulfonamide.Aromatic halide.Primary amine | Sulfonamide.Aromatic halide.Secondary amide | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccccc1.c1ccsc1.c1ccncc1 | HCl | null | null | null | CC(C)(C)NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Cl)cc1.Nc1ccsc1C(=O)Nc1cc(Cl)ccn1>>NS(=O)(=O)c1ccccc1-c1ccc(C(=O)Nc2ccsc2C(=O)Nc2ccc(Cl)cn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-07517b26e624478c890fb3c51e114cc6 | CC1=CC(=O)OC1=O.Nc1ccc(Br)cn1>>CC1=CC(=O)N(c2ccc(Br)cn2)C1=O | C1(\C(\C)=C/C(=O)O1)=O.NC1=NC=C(C=C1)Br>>BrC=1C=CC(=NC1)N1C(C(=CC1=O)C)=O | O1[C:4](=[O:5])[CH:3]=[C:2]([CH3:1])[C:14]1=[O:15].[NH2:6][c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][n:13]1>>[CH3:1][C:2]1=[CH:3][C:4](=[O:5])[N:6]([c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][n:13]2)[C:14]1=[O:15] | CC1=CC(=O)OC1=O.Nc1ccc(Br)cn1 | CC1=CC(=O)N(c2ccc(Br)cn2)C1=O | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | cab1acd179957d4f5c27ba23f314ee257f7d508deff2838c7964b1019063e651 | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1C=CC(=O)N1c1ccccn1 | [C;D1;H3:1]-[C:2]1=[C:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-O-[C;H0;D3;+0:6]-1=[O;D1;H0:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[#7;a:11]:[c:12]>>[C;D1;H3:1]-[C:2]1=[C:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[N;H0;D3;+0:8](-[c:9](:[c:10]):[#7;a:11]:[c:12])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | 71 | [{"value": 71.0, "product": "BrC=1C=CC(=NC1)N1C(C(=CC1=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.8, "product": "BrC=1C=CC(=NC1)N1C(C(=CC1=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of citraconic anhydride (1.00 mL, 11.1 mmol) and 2-amino-5-bromopyridine (1.93 g, 11.2 mmol) in toluene (60 mL) was heated to reflux overnight. The solution was cooled down, filtered. The filtrate was concentrated in vacuo to give a solid (2.10 g, yield: 71%). MS 267 and 269 (M+H).
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | C1=CCOC1 | C1=CC[NH]C1 | C1=CC[NH]C1.c1ccncc1 | HO- | C1(=CC=CC=C1)C | null | null | CC1=CC(=O)OC1=O.Nc1ccc(Br)cn1>C1(=CC=CC=C1)C>CC1=CC(=O)N(c2ccc(Br)cn2)C1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ef5f9d8f8a9f41c1a294046e59611590 | N#Cc1cccc(O)c1.O=[N+]([O-])c1ccccc1F>>N#Cc1cccc(Oc2ccccc2[N+](=O)[O-])c1 | FC1=C(C=CC=C1)[N+](=O)[O-].OC=1C=C(C#N)C=CC1.C(=O)([O-])[O-].[K+].[K+]>>[N+](=O)([O-])C1=C(OC=2C=C(C#N)C=CC2)C=CC=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([OH:8])[cH:18]1.F[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[N+:15](=[O:16])[O-:17]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[N+:15](=[O:16])[O-:17])[cH:18]1 | N#Cc1cccc(O)c1.O=[N+]([O-])c1ccccc1F | N#Cc1cccc(Oc2ccccc2[N+](=O)[O-])c1 | null | null | CCOC(=O)C.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | e4ea1e38252bc3b9c5ec04486386725e6570ab3860d45e337a1d131319bbf0fc | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:2]:[c:3] | 99.2 | [{"value": 99.0, "product": "[N+](=O)([O-])C1=C(OC=2C=C(C#N)C=CC2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.2, "product": "[N+](=O)([O-])C1=C(OC=2C=C(C#N)C=CC2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 3 | HOUR | To a solution of 2-fluoro nitrobenzene (1.41 g, 10 mmol, 1.0 equiv) and 3-hydroxybenzonitrile (1.19 g, 1.0 equiv) in 10 mL of DMF was added K2CO3 (2.76 g, 2 equiv). After stirring at 60° C. for 3 h, the mixture was diluted with EtOAc and washed with H2O. The organic layer was dried over MgSO4, filtered and evaporated t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | CCOC(=O)C.CN(C)C=O | 60 | 3 | N#Cc1cccc(O)c1.O=[N+]([O-])c1ccccc1F>CCOC(=O)C.CN(C)C=O>N#Cc1cccc(Oc2ccccc2[N+](=O)[O-])c1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-23a25129716941e9a600ead660148e17 | N#Cc1cccc(Oc2ccccc2[N+](=O)[O-])c1>>N#Cc1cccc(Oc2ccccc2N)c1 | [N+](=O)([O-])C1=C(OC=2C=C(C#N)C=CC2)C=CC=C1.O.O.Cl[Sn]Cl>>NC1=C(OC=2C=C(C#N)C=CC2)C=CC=C1 | O=[N+:15]([O-])[c:14]1[c:9]([O:8][c:7]2[cH:6][cH:5][cH:4][c:3]([C:2]#[N:1])[cH:16]2)[cH:10][cH:11][cH:12][cH:13]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[NH2:15])[cH:16]1 | N#Cc1cccc(Oc2ccccc2[N+](=O)[O-])c1 | N#Cc1cccc(Oc2ccccc2N)c1 | null | null | CCO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Oc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99 | [{"value": 99.0, "product": "NC1=C(OC=2C=C(C#N)C=CC2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.9, "product": "NC1=C(OC=2C=C(C#N)C=CC2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-(2-nitrophenoxy)benzonitrile (1.21 g, 5 mmol, 1.0 equiv) in 30 mL of EtOH was treated with SnCl2.2H2O (3.38 g, 3 equiv) at reflux for 4 h. The volatile was evaporated and the residue was redissolved in EtOAc, washed with saturated aqueous NaHCO3 and 1N NaOH. The organic layer was dried over MgSO4, filte... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | CCO | null | null | N#Cc1cccc(Oc2ccccc2[N+](=O)[O-])c1>CCO>N#Cc1cccc(Oc2ccccc2N)c1 |
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