dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c3612eda4c6d45ed866635a3ac024e58 | Clc1ccc(CBr)cc1.OCCO>>OCCOCc1ccc(Cl)cc1 | BrCC1=CC=C(C=C1)Cl.O.C(CO)O.[H-].[Na+].BrCC1=CC=C(C=C1)Cl>>ClC1=CC=C(C=C1)COCCO | Br[CH2:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1.[OH:1][CH2:2][CH2:3][OH:4]>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1 | Clc1ccc(CBr)cc1.OCCO | OCCOCc1ccc(Cl)cc1 | null | [N+](CCCC)(CCCC)(CCCC)CCCC.[I-] | CCOC(=O)C.C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 75 | [{"value": 75.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.0, "product": "ClC1=CC=C(C=C1)COCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.1, "product": "ClC1=CC=C(C=C1)COCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | Ethylene glycol (0.084 mL, 1.5 mmol) was added to NaH (38 mg, 1.52 mmol, 95% in oil) in THF (3 mL). 1-(Bromomethyl)-4-chlorobenzene (310 mg, 1.5 mmol) was added to the reaction, and the residual 1-(bromomethyl)-4-chlorobenzene was transferred to the reaction tube with additional THF (1 mL). (Bu)4NI (55 mg, 0.15 mmol) w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HBr | [N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CCOC(=O)C.C1CCOC1 | 60 | 4 | Clc1ccc(CBr)cc1.OCCO>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CCOC(=O)C.C1CCOC1>OCCOCc1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c08c9cc22e4f4c128ea4fe4967b73613 | Clc1ccc(COCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOCc3ccc(Cl)cc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCOCC1=CC=C(C=C1)Cl>>[Br-].ClC1=CC=C(C=C1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH2:19]([CH2:20][O:21][CH2:22][c:23]1[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]1)[Br:34].[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:15]12[CH2:16][CH2:17][N:18]([CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH... | Clc1ccc(COCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOCc3ccc(Cl)cc3)(CC1)CC2.[Br-] | null | null | CC#N.C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 32 | [{"value": 32.0, "product": "[Br-].ClC1=CC=C(C=C1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.4, "product": "[Br-].ClC1=CC=C(C=C1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 1-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (30 mg, 0.102 mmol) was added to a solution of 1-{[(2-bromoethyl)oxy]methyl}-4-chlorobenzene (36 mg, 0.143 mmol) in 2:3 CH3CN/CHCl3 (3 mL), and the reaction was heated at 60° C. for 96 h. The reaction was concentrated, and the crude product was washed with EtOAc (3×1 mL). T... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N.C(Cl)(Cl)Cl | 60 | null | Clc1ccc(COCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N.C(Cl)(Cl)Cl>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOCc3ccc(Cl)cc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da195746e8b64585a4d8579f249cf33d | BrCc1ccc(Br)cc1.OCCO>>OCCOCc1ccc(Br)cc1 | BrC1=CC=C(C=C1)CBr.O.C(CO)O.[H-].[Na+].BrC1=CC=C(C=C1)CBr>>BrC1=CC=C(C=C1)COCCO | Br[CH2:5][c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1.[OH:1][CH2:2][CH2:3][OH:4]>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1 | BrCc1ccc(Br)cc1.OCCO | OCCOCc1ccc(Br)cc1 | null | [N+](CCCC)(CCCC)(CCCC)CCCC.[I-] | CCOC(=O)C.C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 75 | [{"value": 75.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.0, "product": "BrC1=CC=C(C=C1)COCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.1, "product": "BrC1=CC=C(C=C1)COCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | Ethylene glycol (0.084 mL, 1.5 mmol) was added to NaH (38 mg, 1.52 mmol, 95% in oil) in THF (3 mL). 1-Bromo-4-(bromomethyl)benzene (370 mg, 1.5 mmol) was added to the reaction, and the residual 1-bromo-4-(bromomethyl)benzene was transferred to the reaction tube with additional THF (1 mL). (Bu)4NI (55 mg, 0.15 mmol) was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HBr | [N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CCOC(=O)C.C1CCOC1 | 60 | 4 | BrCc1ccc(Br)cc1.OCCO>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CCOC(=O)C.C1CCOC1>OCCOCc1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8cc54ebbce0942e7bc7ba981a5739e70 | BrCCOCc1ccc(Br)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOCc3ccc(Br)cc3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrC1=CC=C(C=C1)COCCBr>>[Br-].BrC1=CC=C(C=C1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH2:19]([CH2:20][O:21][CH2:22][c:23]1[cH:24][cH:25][c:26]([Br:27])[cH:28][cH:29]1)[Br:34].[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:15]12[CH2:16][CH2:17][N:18]([CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH... | BrCCOCc1ccc(Br)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOCc3ccc(Br)cc3)(CC1)CC2.[Br-] | null | null | CC#N.C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 46.2 | [{"value": 32.0, "product": "[Br-].BrC1=CC=C(C=C1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.2, "product": "[Br-].BrC1=CC=C(C=C1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 1-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (30 mg, 0.102 mmol) was added to a solution of 1-bromo-4-{[(2-bromoethyl)oxy]methyl}benzene (42 mg, 0.143 mmol) in 2:3 CH3CN/CHCl3 (3 mL), and the reaction was heated at 60° C. for 96 h. The reaction was concentrated, and the crude product was washed with EtOAc (3×1 mL). Th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N.C(Cl)(Cl)Cl | 60 | null | BrCCOCc1ccc(Br)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N.C(Cl)(Cl)Cl>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOCc3ccc(Br)cc3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1a5ebfa91f4c475b8fcde201942fbe7d | N#Cc1ccc(CBr)cc1.OCCO>>N#Cc1ccc(COCCO)cc1 | BrCC1=CC=C(C#N)C=C1.O.C(CO)O.[H-].[Na+].BrCC1=CC=C(C#N)C=C1>>OCCOCC1=CC=C(C#N)C=C1 | Br[CH2:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:13][cH:12]1.[OH:8][CH2:9][CH2:10][OH:11]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][CH2:9][CH2:10][OH:11])[cH:12][cH:13]1 | N#Cc1ccc(CBr)cc1.OCCO | N#Cc1ccc(COCCO)cc1 | null | [N+](CCCC)(CCCC)(CCCC)CCCC.[I-] | CCOC(=O)C.C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 75 | [{"value": 75.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.0, "product": "OCCOCC1=CC=C(C#N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.7, "product": "OCCOCC1=CC=C(C#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 4 | HOUR | Ethylene glycol (0.084 mL, 1.5 mmol) was added to NaH (38 mg, 1.52 mmol, 95% in oil) in THF (3 mL). 4-(Bromomethyl)benzonitrile (290 mg, 1.5 mmol) was added to the reaction, and the residual 4-(bromomethyl)benzonitrile was transferred to the reaction tube with additional THF (1 mL). (Bu)4NI (55 mg, 0.15 mmol) was then ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HBr | [N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CCOC(=O)C.C1CCOC1 | 60 | 4 | N#Cc1ccc(CBr)cc1.OCCO>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CCOC(=O)C.C1CCOC1>N#Cc1ccc(COCCO)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1949db0ade904857b83552841853c8d4 | N#Cc1ccc(COCCO)cc1.O=C1CCC(=O)N1Br>>N#Cc1ccc(COCCBr)cc1 | OCCOCC1=CC=C(C#N)C=C1.BrN1C(CCC1=O)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCOCC1=CC=C(C#N)C=C1 | O[CH2:10][CH2:9][O:8][CH2:7][c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:13][cH:12]1.O=C1CCC(=O)N1[Br:11]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][CH2:9][CH2:10][Br:11])[cH:12][cH:13]1 | N#Cc1ccc(COCCO)cc1.O=C1CCC(=O)N1Br | N#Cc1ccc(COCCBr)cc1 | null | null | [Al].C(Cl)Cl | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[#8:3].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:4]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[Br;H0;D1;+0:4] | 50 | [{"value": 50.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.0, "product": "BrCCOCC1=CC=C(C#N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.6, "product": "BrCCOCC1=CC=C(C#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of N-bromosuccinimide (272 mg, 1.53 mmol) in DCM (2.5 mL) was added to resin-bound triphenylphosphine (510 mg, 1.53 mEquiv, Fluka) in DCM (2.5 mL), and the reaction was stirred at rt for 10 min. A solution of 4-{[(2-hydroxyethyl)oxy]methyl}benzonitrile (95 mg, 0.536 mmol) in DCM (1.5 mL) was added to the rea... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | [Al].C(Cl)Cl | null | 0.166667 | N#Cc1ccc(COCCO)cc1.O=C1CCC(=O)N1Br>[Al].C(Cl)Cl>N#Cc1ccc(COCCBr)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c3ffc18703b44e8d8bbea0187632040a | N#Cc1ccc(COCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>N#Cc1ccc(COCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)cc1.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCOCC1=CC=C(C#N)C=C1>>[Br-].C(#N)C1=CC=C(C=C1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][CH2:9][CH2:10][Br:35])[cH:33][cH:34]1.[N:11]12[CH2:12][CH2:13][C:14]([C:15]([OH:16])([c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)([CH2:29][CH2:30]1)[CH2:31][CH2:32]2>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][CH2:9][CH2:10... | N#Cc1ccc(COCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | N#Cc1ccc(COCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)cc1.[Br-] | null | null | CC#N.C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 74 | [{"value": 74.0, "product": "[Br-].C(#N)C1=CC=C(C=C1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.5, "product": "[Br-].C(#N)C1=CC=C(C=C1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 1-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (30 mg, 0.102 mmol) was added to a solution of 4-{[(2-bromoethyl)oxy]methyl}benzonitrile (34 mg, 0.143 mmol) in 2:3 CH3CN/CHCl3 (3 mL), and the reaction was heated at 60° C. for 96 h. The reaction was concentrated, and the crude product was washed with EtOAc (3×1 mL). The p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N.C(Cl)(Cl)Cl | 60 | null | N#Cc1ccc(COCCBr)cc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N.C(Cl)(Cl)Cl>N#Cc1ccc(COCC[N+]23CCC(C(O)(c4ccccc4)c4ccccc4)(CC2)CC3)cc1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef216c40e654422aae51dcb913551bbb | O=C1CCC(=O)N1Br.OCCOCc1ccc2ccccc2c1>>BrCCOCc1ccc2ccccc2c1 | C1=C(C=CC2=CC=CC=C12)COCCO.BrN1C(CCC1=O)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCCOCC1=CC2=CC=CC=C2C=C1 | O=C1CCC(=O)N1[Br:1].O[CH2:2][CH2:3][O:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[cH:15]1>>[Br:1][CH2:2][CH2:3][O:4][CH2:5][c:6]1[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[cH:15]1 | O=C1CCC(=O)N1Br.OCCOCc1ccc2ccccc2c1 | BrCCOCc1ccc2ccccc2c1 | null | null | [Al].C(Cl)Cl | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | c1ccc2ccccc2c1 | O-[CH2;D2;+0:1]-[C:2]-[#8:3].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:4]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[Br;H0;D1;+0:4] | 50 | [{"value": 50.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.0, "product": "BrCCOCC1=CC2=CC=CC=C2C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.1, "product": "BrCCOCC1=CC2=CC=CC=C2C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of N-bromosuccinimide (272 mg, 1.53 mmol) in DCM (2.5 mL) was added to resin-bound triphenylphosphine (510 mg, 1.53 mEquiv, Fluka) in DCM (2.5 mL), and the reaction was stirred at rt for 10 min. A solution 2-[(2-naphthalenylmethyl)oxy]ethanol (101 mg, 0.499 mmol) in DCM (1.5 mL) was added to the reaction, an... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | c1ccc2ccccc2c1 | HO- | [Al].C(Cl)Cl | null | 0.166667 | O=C1CCC(=O)N1Br.OCCOCc1ccc2ccccc2c1>[Al].C(Cl)Cl>BrCCOCc1ccc2ccccc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e8994a2447bc4b6f8cc1ec95c995d207 | O=C1CCC(=O)N1Br.OCCOCc1cccc(F)c1>>Fc1cccc(COCCBr)c1 | BrN1C(CCC1=O)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.FC=1C=C(C=CC1)COCCO>>BrCCOCC1=CC(=CC=C1)F | O=C1CCC(=O)N1[Br:11].O[CH2:10][CH2:9][O:8][CH2:7][c:6]1[cH:5][cH:4][cH:3][c:2]([F:1])[cH:12]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][O:8][CH2:9][CH2:10][Br:11])[cH:12]1 | O=C1CCC(=O)N1Br.OCCOCc1cccc(F)c1 | Fc1cccc(COCCBr)c1 | null | null | [Al].C(Cl)Cl | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[#8:3].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:4]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[Br;H0;D1;+0:4] | 78.3 | [{"value": 50.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.0, "product": "BrCCOCC1=CC(=CC=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.3, "product": "BrCCOCC1=CC(=CC=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | N-bromosuccinimide (146 mg, 0.820 mmol) was added to resin-bound triphenylphosphine (274 mg, 0.822 mEquiv, Fluka) and 2-{[(3-fluorophenyl)methyl]oxy}ethanol (70 mg, 0.411 mmol) in DCM (4 mL). The reaction vial was sealed with a Teflon-lined cap, wrapped in aluminum foil, and shaken at rt for 17 h. The reaction was filt... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | [Al].C(Cl)Cl | null | 17 | O=C1CCC(=O)N1Br.OCCOCc1cccc(F)c1>[Al].C(Cl)Cl>Fc1cccc(COCCBr)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-88b5c8bb1642445bb21d30a6f962e3d2 | Fc1cccc(COCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOCc3cccc(F)c3)(CC1)CC2.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCOCC1=CC(=CC=C1)F>>[Br-].FC=1C=C(C=CC1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O | [CH2:19]([CH2:20][O:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][c:27]([F:28])[cH:29]1)[Br:34].[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:15]12[CH2:16][CH2:17][N:18]([CH2:30][CH2:31]1)[CH2:32][CH2:33]2>>[OH:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([c:9]1[cH:10][cH:... | Fc1cccc(COCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOCc3cccc(F)c3)(CC1)CC2.[Br-] | null | null | CC#N.C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 30 | [{"value": 30.0, "product": "[Br-].FC=1C=C(C=CC1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.6, "product": "[Br-].FC=1C=C(C=CC1)COCC[N+]12CCC(CC1)(CC2)C(C2=CC=CC=C2)(C2=CC=CC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 1-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (94 mg, 0.321 mmol) was added to a solution of 1-{[(2-bromoethyl)oxy]methyl}-3-fluorobenzene (75 mg, 0.321 mmol) in 2:3 CH3CN/CHCl3 (4 mL), and the reaction was heated at 60° C. for 3 days. The reaction was concentrated under reduced pressure, and the crude product was wash... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N.C(Cl)(Cl)Cl | 60 | null | Fc1cccc(COCCBr)c1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N.C(Cl)(Cl)Cl>OC(c1ccccc1)(c1ccccc1)C12CC[N+](CCOCc3cccc(F)c3)(CC1)CC2.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6b4c6e3ee2ac48639c228ce6b5bd67b4 | CC(C)(OCCO)c1ccccc1.O=C1CCC(=O)N1Br>>CC(C)(OCCBr)c1ccccc1 | BrN1C(CCC1=O)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CC(C)(C1=CC=CC=C1)OCCO>>BrCCOC(C)(C)C1=CC=CC=C1 | O[CH2:6][CH2:5][O:4][C:2]([CH3:1])([CH3:3])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.O=C1CCC(=O)N1[Br:7]>>[CH3:1][C:2]([CH3:3])([O:4][CH2:5][CH2:6][Br:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | CC(C)(OCCO)c1ccccc1.O=C1CCC(=O)N1Br | CC(C)(OCCBr)c1ccccc1 | null | null | [Al].C(Cl)Cl | Functional Group Interconversion | OtherReaction | f5aab884336f72e1370119b83151f1b95e31e5f052f259aee44382a5b9c14686 | 2aeb112456268e3e5dab065a03bb8fc4b6e8f1d07cae05ef26dce278613b654e | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[#8:3].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:4]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[Br;H0;D1;+0:4] | 50 | [{"value": 50.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.0, "product": "BrCCOC(C)(C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.0, "product": "BrCCOC(C)(C)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | N-bromosuccinimide (119 mg, 0.666 mmol) was added to resin-bound triphenylphosphine (222 mg, 0.666 mEquiv, Fluka) and 2-[(1-methyl-1-phenylethyl)oxy]ethanol (60 mg, 0.333 mmol) in DCM (4 mL). The reaction vial was sealed with a Teflon-lined cap, wrapped in aluminum foil, and shaken at rt for 17 h. The reaction was filt... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Primary alcohol | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | [Al].C(Cl)Cl | null | 17 | CC(C)(OCCO)c1ccccc1.O=C1CCC(=O)N1Br>[Al].C(Cl)Cl>CC(C)(OCCBr)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1f9533b920e545919121d1e736f1ba9c | CC(C)(OCCBr)c1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>CC(C)(OCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2)c1ccccc1.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.BrCCOC(C)(C)C1=CC=CC=C1>>[Br-].OC(C12CC[N+](CC1)(CC2)CCOC(C)(C2=CC=CC=C2)C)(C2=CC=CC=C2)C2=CC=CC=C2 | [CH3:1][C:2]([CH3:3])([O:4][CH2:5][CH2:6][Br:35])[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1.[N:7]12[CH2:8][CH2:9][C:10]([C:11]([OH:12])([c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)([CH2:25][CH2:26]1)[CH2:27][CH2:28]2>>[CH3:1][C:2]([CH3:3])([O:4][CH2:5][CH2:6][N+:7]12[CH2:8][... | CC(C)(OCCBr)c1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | CC(C)(OCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2)c1ccccc1.[Br-] | null | null | CC#N.C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 551ca9b38c767f8ca3093ced0cf834ba6857d4c8d7d9b3db122be6576377e292 | 3d861fb9efedfc352e8049eef974a995ad6d89e50a2cf826c8f45bd07b1b8172 | c1ccc(COCC[N+]23CCC(C(c4ccccc4)c4ccccc4)(CC2)CC3)cc1 | [#8:1]-[C:2]-[CH2;D2;+0:3]-[Br;H0;D1;+0:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[C:10]-[C:11]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[N+;H0;D4:7](-[C:6]-[C:5])(-[C:8]-[C:9])-[C:10]-[C:11].[Br-;H0;D0:4] | 24 | [{"value": 24.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOC(C)(C2=CC=CC=C2)C)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.0, "product": "[Br-].OC(C12CC[N+](CC1)(CC2)CCOC(C)(C2=CC=CC=C2)C)(C2=CC=CC=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | 1-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (41 mg, 0.14 mmol) was added to a solution of {1-[(2-bromoethyl)oxy]-1-methylethyl}benzene (34 mg, 0.14 mmol) in 2:3 CH3CN/CHCl3 (3 mL), and the reaction was heated at 60° C. for 3 days. The reaction was concentrated under reduced pressure, and the crude product was washed ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Tertiary amine | null | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH+]2CCC1CC2 | null | CC#N.C(Cl)(Cl)Cl | 60 | null | CC(C)(OCCBr)c1ccccc1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CC#N.C(Cl)(Cl)Cl>CC(C)(OCC[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2)c1ccccc1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c505c9a2b8534f8c9ac6527f9b6b81f2 | O=C(CBr)c1cc2ccccc2o1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>>O=C(C[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2)c1cc2ccccc2o1.[Br-] | N12CCC(CC1)(CC2)C(O)(C2=CC=CC=C2)C2=CC=CC=C2.O1C(=CC2=C1C=CC=C2)C(CBr)=O.CC#N>>[Br-].O1C(=CC2=C1C=CC=C2)C(C[N+]21CCC(CC2)(CC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)O)=O | [O:1]=[C:2]([CH2:3][Br:35])[c:26]1[cH:27][c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[o:34]1.[N:4]12[CH2:5][CH2:6][C:7]([C:8]([OH:9])([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)([CH2:22][CH2:23]1)[CH2:24][CH2:25]2>>[O:1]=[C:2]([CH2:3][N+:4]12[CH2:5][CH2:6][C:7]([C:8]([OH:9])([... | O=C(CBr)c1cc2ccccc2o1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2 | O=C(C[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2)c1cc2ccccc2o1.[Br-] | null | null | CS(=O)C.C(Cl)(Cl)Cl | Functional Group Interconversion | OtherReaction | 52967c6c525f6fd449388f2f21be62ee27cce2784f49d80eefef6fdd2bffd668 | 9b4d821c54deb0cc19603ec7f579dca6c7b9d0b891b757664ed6185aa11a3daf | O=C(C[N+]12CCC(C(c3ccccc3)c3ccccc3)(CC1)CC2)c1cc2ccccc2o1 | [#8;a:1]:[c:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[Br;H0;D1;+0:6].[C:7]-[C:8]-[N;H0;D3;+0:9](-[C:10]-[C:11])-[C:12]-[C:13]>>[#8;a:1]:[c:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[N+;H0;D4:9](-[C:8]-[C:7])(-[C:10]-[C:11])-[C:12]-[C:13].[Br-;H0;D0:6] | 57.4 | [{"value": 57.4, "product": "[Br-].O1C(=CC2=C1C=CC=C2)C(C[N+]21CCC(CC2)(CC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.1, "product": "[Br-].O1C(=CC2=C1C=CC=C2)C(C[N+]21CCC(CC2)(CC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | 60 | CELSIUS | null | null | 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (0.022 g, 0.075 mmol) was diluted in CHCl3 (1.8 mL) and dispensed directly into a 1 dram vial containing 1-(1-benzofuran-2-yl)-2-bromoethanone (0.027 g, 0.112 mmol). Added CH3CN (1.2 mL), the vial was fitted with stirring bar and capped. The reaction was stirred and heated ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Tertiary amine | Ketone | C1CN2CCC1CC2 | C1C[NH+]2CCC1CC2 | c1ccccc1.c1ccccc1.c1ccc2occc2c1.C1C[NH+]2CCC1CC2 | null | CS(=O)C.C(Cl)(Cl)Cl | 60 | null | O=C(CBr)c1cc2ccccc2o1.OC(c1ccccc1)(c1ccccc1)C12CCN(CC1)CC2>CS(=O)C.C(Cl)(Cl)Cl>O=C(C[N+]12CCC(C(O)(c3ccccc3)c3ccccc3)(CC1)CC2)c1cc2ccccc2o1.[Br-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f3523d38dea04e2c9576e6728fb67648 | CCc1nc(C)c(CCO)s1.O=[N+]([O-])O>>CCc1nc(C)c(CCO[N+](=O)[O-])s1 | C(C)C=1SC(=C(N1)C)CCO.[N+](=O)(O)[O-].S(O)(O)(=O)=O.[OH-].[Na+]>>C(C)C=1SC(=C(N1)C)CCO[N+](=O)[O-] | [CH3:1][CH2:2][c:3]1[n:4][c:5]([CH3:6])[c:7]([CH2:8][CH2:9][OH:10])[s:14]1.O[N+:11](=[O:12])[O-:13]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH3:6])[c:7]([CH2:8][CH2:9][O:10][N+:11](=[O:12])[O-:13])[s:14]1 | CCc1nc(C)c(CCO)s1.O=[N+]([O-])O | CCc1nc(C)c(CCO[N+](=O)[O-])s1 | null | null | O.CCCCCC | Functional Group Addition | OtherReaction | 6714972cf15c902e80468dfc00bd4702061f399559dac18663a04d0313578c58 | 56c31f2adb3c5cef6a017f5700f56bb2235baa5ecf98cc42dc8ccc6b8370bd25 | c1cscn1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3] | 58 | [{"value": 58.0, "product": "C(C)C=1SC(=C(N1)C)CCO[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | 2.5 | CELSIUS | 2 | HOUR | Fifteen (15) ml of nitric acid of (85-90%) were added dropwise to 15 ml of sulfuric acid (95-98%) over a time period of 20 minutes while keeping the temperature at 0-5° C. After 2 hours, 14.3 grams (83.60 mmole) of 2-ethyl-4-methyl-5-thiazoleethanol, prepared as described above, were added, while the temperature was st... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate.Primary alcohol | Nitrate | null | null | c1cscn1 | HO- | O.CCCCCC | 2.5 | 2 | CCc1nc(C)c(CCO)s1.O=[N+]([O-])O>O.CCCCCC>CCc1nc(C)c(CCO[N+](=O)[O-])s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d2b3e0b8d1334f7cb73bf12a5c35f31c | CC(=O)OCCC(Cl)C(C)=O.NC(N)=S>>Cc1nc(N)sc1CCO | NC(=S)N.C(C)(=O)OCCC(C(C)=O)Cl>>NC=1SC(=C(N1)C)CCO | CC(=O)[O:10][CH2:9][CH2:8][CH:7](Cl)[C:2](=O)[CH3:1].[NH2:3][C:4]([NH2:5])=[S:6]>>[CH3:1][c:2]1[n:3][c:4]([NH2:5])[s:6][c:7]1[CH2:8][CH2:9][OH:10] | CC(=O)OCCC(Cl)C(C)=O.NC(N)=S | Cc1nc(N)sc1CCO | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | b3c7ffcdfaa4e8556a9a3a0b684936f49f37ece8c04355b09719cc5bcd1d4acb | 4f627485f64841b5f8e456533089e71eb2604122f0ef3312d8d7ac771245aa1e | c1cscn1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]-[CH;D3;+0:4](-Cl)-[C;H0;D3;+0:5](=O)-[C;D1;H3:6].[N;D1;H2:7]-[C;H0;D3;+0:8](-[NH2;D1;+0:9])=[S;H0;D1;+0:10]>>[C;D1;H3:6]-[c;H0;D3;+0:5]1:[n;H0;D2;+0:9]:[c;H0;D3;+0:8](-[N;D1;H2:7]):[s;H0;D2;+0:10]:[c;H0;D3;+0:4]:1-[C:3]-[C:2]-[OH;D1;+0:1] | 72 | [{"value": 72.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 2-(2-Amino-4-methyl-thiazol-5-yl)-ethanol was prepared according to general procedures presented hereinabove, by adding 20 grams (0.263 moles) of thiourea to 200 ml of dry toluene, followed by addition of 47 grams (0.263 moles) of 5-acetoxy-3-chloro-2-pentanone over a time period of 20 minutes. The reaction mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ketone.Ester.Thiourea | Primary alcohol | null | c1cscn1 | c1cscn1 | HCl | C1(=CC=CC=C1)C | 80 | null | CC(=O)OCCC(Cl)C(C)=O.NC(N)=S>C1(=CC=CC=C1)C>Cc1nc(N)sc1CCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3827bb123715487491da1dadc3313d18 | Cc1nc(N)sc1CCO.O=[N+]([O-])O>>Cc1nc(N)sc1CCO[N+](=O)[O-] | NC=1SC(=C(N1)C)CCO.[N+](=O)(O)[O-].S(O)(O)(=O)=O.[OH-].[Na+].NC=1SC(=C(N1)C)CCO>>CC=1N=C(SC1CCO[N+](=O)[O-])N | O[CH2:9][CH2:8][c:7]1[c:2]([CH3:1])[n:3][c:4]([NH2:5])[s:6]1.[OH:10][N+:11](=[O:12])[O-:13]>>[CH3:1][c:2]1[n:3][c:4]([NH2:5])[s:6][c:7]1[CH2:8][CH2:9][O:10][N+:11](=[O:12])[O-:13] | Cc1nc(N)sc1CCO.O=[N+]([O-])O | Cc1nc(N)sc1CCO[N+](=O)[O-] | null | null | CCCCCC.O | Heteroatom Alkylation and Arylation | OtherReaction | 0fcd381b777d6629b0c9e6356597dd7aaabef76c7dfe47721d8d10b5fc8adb37 | 2ab4024aa17b6e89368e6fe8ee731d32c7611cb9b23de403e301e8362fea90b1 | c1cscn1 | O-[CH2;D2;+0:1]-[C:2]-[c:3](:[#16;a:4]):[c:5]:[#7;a:6].[O;-;D1;H0:7]-[#7;+:8](=[O;D1;H0:9])-[OH;D1;+0:10]>>[#16;a:4]:[c:3](-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[#7;+:8](-[O;-;D1;H0:7])=[O;D1;H0:9]):[c:5]:[#7;a:6] | 35 | [{"value": 35.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 3 | HOUR | Subsequently, 4-methyl-5-(2-nitrooxy-ethyl)-thiazole-2-ylamine was prepared by drop-wise addition of 1.59 grams of nitric acid (70%) to 2.48 grams of cooled sulfuric acid (95-98%) at 0-5° C. over a time period of 20 minutes. Following, 4 grams (0.025 moles) of 2-(2-Amino-4-methyl-thiazol-5-yl)-ethanol were added over a... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | c1cscn1 | HO- | CCCCCC.O | 25 | 3 | Cc1nc(N)sc1CCO.O=[N+]([O-])O>CCCCCC.O>Cc1nc(N)sc1CCO[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-88c60881f4094a009dcda25f699fbe6a | CO.Cc1ccccc1.NC(=S)c1cccnc1>>Cc1nc(-c2cccnc2)sc1CCO | CO.C(C1=CN=CC=C1)(=S)N.C1(=CC=CC=C1)C>>CC=1N=C(SC1CCO)C=1C=NC=CC1 | [CH3:14][OH:15].c1c[c:2]([CH3:1])[cH:12][cH:13]c1.[NH2:3][C:4]([c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1)=[S:11]>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][n:9][cH:10]2)[s:11][c:12]1[CH2:13][CH2:14][OH:15] | CO.Cc1ccccc1.NC(=S)c1cccnc1 | Cc1nc(-c2cccnc2)sc1CCO | null | null | null | C-C Coupling | OtherReaction | 1603bc26d4737ee6b1ef5c542f76023e106083e9ce28422ecf892406fe3aecff | e94b02b273fdd34e1629f268a3d00d66649efede4f293502196cb20007b61f4e | c1cncc(-c2nccs2)c1 | [C;D1;H3:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:c:c:c:1.[CH3;D1;+0:5]-[O;D1;H1:6].[NH2;D1;+0:7]-[C;H0;D3;+0:8](=[S;H0;D1;+0:9])-[c;H0;D3;+0:10]1:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:1>>[C;D1;H3:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:8](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[c:13]:[c:14]:[c:15]:2):[s;H0;D2;+0... | 31 | [{"value": 31.0, "product": "CC=1N=C(SC1CCO)C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 1 | HOUR | 2-(4-Methyl-2-pyridin-3-yl-thiazole-5-yl)-ethanol was prepared according to the general procedure presented hereinabove, by adding 20 grams (0.145 moles) of thionicotinamide (purchased from Acros, Belgium) to 200 ml of dry toluene, followed by addition of 26 grams (0.145 moles) of ACP over a time period of 20 minutes. ... | 10.6084/m9.figshare.5104873.v1 | null | Thioamide.Methanol | Primary alcohol | c1ccccc1 | c1cscn1 | c1cscn1.c1ccncc1 | Other | null | 80 | 1 | CO.Cc1ccccc1.NC(=S)c1cccnc1>>Cc1nc(-c2cccnc2)sc1CCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-230b5ddd9aae4d52abab35b0234b9d9c | Cc1nc(-c2cccnc2)sc1CCO.O=[N+]([O-])O>>Cc1nc(-c2cccnc2)sc1CCO[N+](=O)[O-] | [OH-].[Na+].[N+](=O)(O)[O-].S(O)(O)(=O)=O.CC=1N=C(SC1CCO)C=1C=NC=CC1>>CC=1N=C(SC1CCO[N+](=O)[O-])C=1C=NC=CC1 | [CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][n:9][cH:10]2)[s:11][c:12]1[CH2:13][CH2:14][OH:15].O[N+:16](=[O:17])[O-:18]>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][n:9][cH:10]2)[s:11][c:12]1[CH2:13][CH2:14][O:15][N+:16](=[O:17])[O-:18] | Cc1nc(-c2cccnc2)sc1CCO.O=[N+]([O-])O | Cc1nc(-c2cccnc2)sc1CCO[N+](=O)[O-] | null | null | O | Functional Group Addition | OtherReaction | 6714972cf15c902e80468dfc00bd4702061f399559dac18663a04d0313578c58 | 56c31f2adb3c5cef6a017f5700f56bb2235baa5ecf98cc42dc8ccc6b8370bd25 | c1cncc(-c2nccs2)c1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3] | 41 | [{"value": 41.0, "product": "CC=1N=C(SC1CCO[N+](=O)[O-])C=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | 2.5 | CELSIUS | 30 | MINUTE | 3-[4-Methyl-5-(2-nitrooxy-ethyl)-thiazole-2-yl]-pyridine was prepared by drop-wise addition of 1.145 gr. of nitric acid (70%) to 1.78 grams of cooled sulfuric acid (95-98%) at 0-5° C., followed by addition of 4 grams (0.0181 moles) 2-(4-methyl-2-pyridin-3-yl-thiazole-5-yl)-ethanol over a time period of 30 minutes at 0-... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate.Primary alcohol | Nitrate | null | null | c1cscn1.c1ccncc1 | HO- | O | 2.5 | 0.5 | Cc1nc(-c2cccnc2)sc1CCO.O=[N+]([O-])O>O>Cc1nc(-c2cccnc2)sc1CCO[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e73a1421b2394df2a99ce3f3b78ab590 | Cc1nc(NC(=O)c2cccnc2)sc1CCO.O=[N+]([O-])O>>Cc1nc(NC(=O)c2cccnc2)sc1CCO[N+](=O)[O-] | C(=O)(O)[O-].[Na+].C(=O)=O.[N+](=O)(O)[O-].C(C)(=O)OC(C)=O.OCCC1=C(N=C(S1)NC(C1=CN=CC=C1)=O)C>>CC=1N=C(SC1CCO[N+](=O)[O-])NC(C1=CN=CC=C1)=O | [CH3:1][c:2]1[n:3][c:4]([NH:5][C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[s:14][c:15]1[CH2:16][CH2:17][OH:18].O[N+:19](=[O:20])[O-:21]>>[CH3:1][c:2]1[n:3][c:4]([NH:5][C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][n:12][cH:13]2)[s:14][c:15]1[CH2:16][CH2:17][O:18][N+:19](=[O:20])[O-:21] | Cc1nc(NC(=O)c2cccnc2)sc1CCO.O=[N+]([O-])O | Cc1nc(NC(=O)c2cccnc2)sc1CCO[N+](=O)[O-] | null | null | null | Functional Group Addition | OtherReaction | 6714972cf15c902e80468dfc00bd4702061f399559dac18663a04d0313578c58 | 56c31f2adb3c5cef6a017f5700f56bb2235baa5ecf98cc42dc8ccc6b8370bd25 | O=C(Nc1nccs1)c1cccnc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3] | null | [] | 25 | CELSIUS | null | null | 70% nitric acid (1.2 ml) was added to acetic anhydride (5 ml) stirring and maintaining the temperture between 20-30° C. by external cooling. The mixture was cooled to −5° C. while stirring, followed by the addition of 1 gram of N-[5-(2-hydroxy-ethyl)-4-methyl-thiazol-2-yl]-nicotinamide. After 30 minutes at −5° C. the m... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate.Primary alcohol | Nitrate | null | null | c1cscn1.c1ccncc1 | HO- | null | 25 | null | Cc1nc(NC(=O)c2cccnc2)sc1CCO.O=[N+]([O-])O>>Cc1nc(NC(=O)c2cccnc2)sc1CCO[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c84105d71d88465885b48352ce306f1d | Cc1nc(N)sc1CCO[N+](=O)[O-].O=C(O)CCCCC1CCSS1>>Cc1nc(NC(=O)CCCCC2CCSS2)sc1CCO[N+](=O)[O-] | S1SC(CC1)CCCCC(=O)O.CC=1N=C(SC1CCO[N+](=O)[O-])N>>CC=1N=C(SC1CCO[N+](=O)[O-])NC(CCCCC1SSCC1)=O | [CH3:1][c:2]1[n:3][c:4]([NH2:5])[s:17][c:18]1[CH2:19][CH2:20][O:21][N+:22](=[O:23])[O-:24].O[C:6](=[O:7])[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH2:13][CH2:14][S:15][S:16]1>>[CH3:1][c:2]1[n:3][c:4]([NH:5][C:6](=[O:7])[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]2[CH2:13][CH2:14][S:15][S:16]2)[s:17][c:18]1[CH2:19][CH2:20][O:21]... | Cc1nc(N)sc1CCO[N+](=O)[O-].O=C(O)CCCCC1CCSS1 | Cc1nc(NC(=O)CCCCC2CCSS2)sc1CCO[N+](=O)[O-] | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCCCC1CCSS1)Nc1nccs1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1 | 51 | [{"value": 51.0, "product": "CC=1N=C(SC1CCO[N+](=O)[O-])NC(CCCCC1SSCC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Pet-151 was prepared according to the general procedure described hereinabove and the procedure described above for the preparation of Pet-154, using 5-[1,2]Dithiolan-3-yl-pentanoic acid (DL-Lipoic acid) and 4-methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylamine (Pet-10) as the starting materials, in an overall yield of 51% a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cscn1.C1CSSC1 | HO- | null | null | null | Cc1nc(N)sc1CCO[N+](=O)[O-].O=C(O)CCCCC1CCSS1>>Cc1nc(NC(=O)CCCCC2CCSS2)sc1CCO[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e7089e2426d4560b96cf5fa1593444c | CC(C)Cc1ccc(C(C)C(=O)O)cc1.Cc1nc(N)sc1CCO[N+](=O)[O-]>>Cc1nc(NC(=O)C(C)c2ccc(CC(C)C)cc2)sc1CCO[N+](=O)[O-] | C(C(C)C)C1=CC=C(C=C1)C(C(=O)O)C.CC=1N=C(SC1CCO[N+](=O)[O-])N>>C(C(C)C)C1=CC=C(C=C1)C(C(=O)NC=1SC(=C(N1)C)CCO[N+](=O)[O-])C | O[C:6](=[O:7])[CH:8]([CH3:9])[c:10]1[cH:11][cH:12][c:13]([CH2:14][CH:15]([CH3:16])[CH3:17])[cH:18][cH:19]1.[CH3:1][c:2]1[n:3][c:4]([NH2:5])[s:20][c:21]1[CH2:22][CH2:23][O:24][N+:25](=[O:26])[O-:27]>>[CH3:1][c:2]1[n:3][c:4]([NH:5][C:6](=[O:7])[CH:8]([CH3:9])[c:10]2[cH:11][cH:12][c:13]([CH2:14][CH:15]([CH3:16])[CH3:17])[... | CC(C)Cc1ccc(C(C)C(=O)O)cc1.Cc1nc(N)sc1CCO[N+](=O)[O-] | Cc1nc(NC(=O)C(C)c2ccc(CC(C)C)cc2)sc1CCO[N+](=O)[O-] | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccccc1)Nc1nccs1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[c:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[C;D1;H3:4]-[C:3](-[c:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1 | 63 | [{"value": 63.0, "product": "C(C(C)C)C1=CC=C(C=C1)C(C(=O)NC=1SC(=C(N1)C)CCO[N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Pet-152 was prepared according to the general procedure described hereinabove and the procedure described above for the preparation of Pet-154, using 2-(4-isobutyl-phenyl)-propionic acid (Ibuprofen) and 4-methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylamine (Pet-10) as the starting materials, in an overall yield of 63%.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cscn1.c1ccccc1 | HO- | null | null | null | CC(C)Cc1ccc(C(C)C(=O)O)cc1.Cc1nc(N)sc1CCO[N+](=O)[O-]>>Cc1nc(NC(=O)C(C)c2ccc(CC(C)C)cc2)sc1CCO[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dc56f15efd22405484bce4547bc8cd31 | CC(=O)Nc1ccc(C(=O)O)cc1.Cc1nc(N)sc1CCO[N+](=O)[O-]>>CC(=O)Nc1ccc(C(=O)Nc2nc(C)c(CCO[N+](=O)[O-])s2)cc1 | C(C)(=O)NC1=CC=C(C(=O)O)C=C1.CC=1N=C(SC1CCO[N+](=O)[O-])N>>C(C)(=O)NC1=CC=C(C(=O)NC=2SC(=C(N2)C)CCO[N+](=O)[O-])C=C1 | O[C:9]([c:8]1[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:25][cH:24]1)=[O:10].[NH2:11][c:12]1[n:13][c:14]([CH3:15])[c:16]([CH2:17][CH2:18][O:19][N+:20](=[O:21])[O-:22])[s:23]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[NH:11][c:12]2[n:13][c:14]([CH3:15])[c:16]([CH2:17][CH2:18][O:19][N+:20](=[... | CC(=O)Nc1ccc(C(=O)O)cc1.Cc1nc(N)sc1CCO[N+](=O)[O-] | CC(=O)Nc1ccc(C(=O)Nc2nc(C)c(CCO[N+](=O)[O-])s2)cc1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1nccs1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1)-[c:3](:[c:4]):[c:5] | 44 | [{"value": 44.0, "product": "C(C)(=O)NC1=CC=C(C(=O)NC=2SC(=C(N2)C)CCO[N+](=O)[O-])C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Pet-157 was prepared according to the general procedure described hereinabove and the procedure described above for the preparation of Pet-154, using 4-acetylamino-benzoic acid and 4-methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylamine (Pet-10) as the starting materials, in an overall yield of 44%.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1cscn1 | HO- | null | null | null | CC(=O)Nc1ccc(C(=O)O)cc1.Cc1nc(N)sc1CCO[N+](=O)[O-]>>CC(=O)Nc1ccc(C(=O)Nc2nc(C)c(CCO[N+](=O)[O-])s2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-09acce9ce1e7441cb249606fd174e3a9 | CCCCCCCCCCCCCCCC(=O)O.Cc1nc(N)sc1CCO[N+](=O)[O-]>>CCCCCCCCCCCCCCCC(=O)Nc1nc(C)c(CCO[N+](=O)[O-])s1 | C(CCCCCCCCCCCCCCC)(=O)O.CC=1N=C(SC1CCO[N+](=O)[O-])N>>CC=1N=C(SC1CCO[N+](=O)[O-])NC(CCCCCCCCCCCCCCC)=O | O[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:17].[NH2:18][c:19]1[n:20][c:21]([CH3:22])[c:23]([CH2:24][CH2:25][O:26][N+:27](=[O:28])[O-:29])[s:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:1... | CCCCCCCCCCCCCCCC(=O)O.Cc1nc(N)sc1CCO[N+](=O)[O-] | CCCCCCCCCCCCCCCC(=O)Nc1nc(C)c(CCO[N+](=O)[O-])s1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1cscn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1 | 62 | [{"value": 62.0, "product": "CC=1N=C(SC1CCO[N+](=O)[O-])NC(CCCCCCCCCCCCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Pet-158 was prepared according to the general procedure described hereinabove and the procedure described above for the preparation of Pet-154, using hexadecanoic acid (palmitic acid) and 4-methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylamine (Pet-10) as the starting materials, in an overall yield of 62%.
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cscn1 | HO- | null | null | null | CCCCCCCCCCCCCCCC(=O)O.Cc1nc(N)sc1CCO[N+](=O)[O-]>>CCCCCCCCCCCCCCCC(=O)Nc1nc(C)c(CCO[N+](=O)[O-])s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fff42f3e4eed464ab837458219e894d9 | CC(=O)Oc1ccccc1C(=O)O.Cc1nc(N)sc1CCO[N+](=O)[O-]>>CC(=O)Oc1ccccc1C(=O)Nc1nc(C)c(CCO[N+](=O)[O-])s1 | C(C)(=O)OC1=C(C(=O)O)C=CC=C1.CC=1N=C(SC1CCO[N+](=O)[O-])N>>CC=1N=C(SC1CCO[N+](=O)[O-])NC(=O)C1=C(C=CC=C1)OC(C)=O | O[C:11]([c:10]1[c:5]([O:4][C:2]([CH3:1])=[O:3])[cH:6][cH:7][cH:8][cH:9]1)=[O:12].[NH2:13][c:14]1[n:15][c:16]([CH3:17])[c:18]([CH2:19][CH2:20][O:21][N+:22](=[O:23])[O-:24])[s:25]1>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11](=[O:12])[NH:13][c:14]1[n:15][c:16]([CH3:17])[c:18]([CH2:19][CH2:20][O:2... | CC(=O)Oc1ccccc1C(=O)O.Cc1nc(N)sc1CCO[N+](=O)[O-] | CC(=O)Oc1ccccc1C(=O)Nc1nc(C)c(CCO[N+](=O)[O-])s1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1nccs1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1)-[c:3](:[c:4]):[c:5] | 25 | [{"value": 25.0, "product": "CC=1N=C(SC1CCO[N+](=O)[O-])NC(=O)C1=C(C=CC=C1)OC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Pet-159 was prepared according to the general procedure described hereinabove and the procedure described above for the preparation of Pet-154, using 2-acetoxy-benzoic acid (Aspirin) and 4-methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylamine (Pet-10) as the starting materials, in an overall yield of 25%.
Conditions: See react... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1cscn1 | HO- | null | null | null | CC(=O)Oc1ccccc1C(=O)O.Cc1nc(N)sc1CCO[N+](=O)[O-]>>CC(=O)Oc1ccccc1C(=O)Nc1nc(C)c(CCO[N+](=O)[O-])s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a706d0f6d47c4b31b53ed9d2c72390aa | Cc1nc(N)sc1CCO[N+](=O)[O-].O=C(O)C1CCCN1>>Cc1nc(NC(=O)C2CCCN2)sc1CCO[N+](=O)[O-] | N1C(CCC1)C(=O)O.CC=1N=C(SC1CCO[N+](=O)[O-])N>>CC=1N=C(SC1CCO[N+](=O)[O-])NC(=O)C1NCCC1 | [CH3:1][c:2]1[n:3][c:4]([NH2:5])[s:13][c:14]1[CH2:15][CH2:16][O:17][N+:18](=[O:19])[O-:20].O[C:6](=[O:7])[CH:8]1[CH2:9][CH2:10][CH2:11][NH:12]1>>[CH3:1][c:2]1[n:3][c:4]([NH:5][C:6](=[O:7])[CH:8]2[CH2:9][CH2:10][CH2:11][NH:12]2)[s:13][c:14]1[CH2:15][CH2:16][O:17][N+:18](=[O:19])[O-:20] | Cc1nc(N)sc1CCO[N+](=O)[O-].O=C(O)C1CCCN1 | Cc1nc(NC(=O)C2CCCN2)sc1CCO[N+](=O)[O-] | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1nccs1)C1CCCN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5]-[C:6].[NH2;D1;+0:7]-[c:8]1:[#16;a:9]:[c:10]:[c:11]:[#7;a:12]:1>>[C:6]-[#7:5]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8]1:[#16;a:9]:[c:10]:[c:11]:[#7;a:12]:1)-[C:4] | 55 | [{"value": 55.0, "product": "CC=1N=C(SC1CCO[N+](=O)[O-])NC(=O)C1NCCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Pet-160 was prepared according to the general procedure described hereinabove and the procedure described above for the preparation of Pet-154, using pyrrolidine-2-carboxylic acid and 4-methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylamine (Pet-10) as the starting materials, in an overall yield of 55%.
Conditions: See reaction... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cscn1.C1CCNC1 | HO- | null | null | null | Cc1nc(N)sc1CCO[N+](=O)[O-].O=C(O)C1CCCN1>>Cc1nc(NC(=O)C2CCCN2)sc1CCO[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-08fd21063e4742b0825fdf63b8fd7d76 | Cc1nc(N)sc1CCO[N+](=O)[O-].O=C(O)c1c(F)cccc1F>>Cc1nc(NC(=O)c2c(F)cccc2F)sc1CCO[N+](=O)[O-] | FC1=C(C(=O)O)C(=CC=C1)F.CC=1N=C(SC1CCO[N+](=O)[O-])N>>FC1=C(C(=O)NC=2SC(=C(N2)C)CCO[N+](=O)[O-])C(=CC=C1)F | [CH3:1][c:2]1[n:3][c:4]([NH2:5])[s:16][c:17]1[CH2:18][CH2:19][O:20][N+:21](=[O:22])[O-:23].O[C:6](=[O:7])[c:8]1[c:9]([F:10])[cH:11][cH:12][cH:13][c:14]1[F:15]>>[CH3:1][c:2]1[n:3][c:4]([NH:5][C:6](=[O:7])[c:8]2[c:9]([F:10])[cH:11][cH:12][cH:13][c:14]2[F:15])[s:16][c:17]1[CH2:18][CH2:19][O:20][N+:21](=[O:22])[O-:23] | Cc1nc(N)sc1CCO[N+](=O)[O-].O=C(O)c1c(F)cccc1F | Cc1nc(NC(=O)c2c(F)cccc2F)sc1CCO[N+](=O)[O-] | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1nccs1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1)-[c:3](:[c:4]):[c:5] | 72 | [{"value": 72.0, "product": "FC1=C(C(=O)NC=2SC(=C(N2)C)CCO[N+](=O)[O-])C(=CC=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Pet-161 was prepared according to the general procedure described hereinabove and the procedure described above for the preparation of Pet-154, using 2,6-difluoro-benzoic acid and 4-methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylamine (Pet-10) as the starting materials, in an overall yield of 72%.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cscn1.c1ccccc1 | HO- | null | null | null | Cc1nc(N)sc1CCO[N+](=O)[O-].O=C(O)c1c(F)cccc1F>>Cc1nc(NC(=O)c2c(F)cccc2F)sc1CCO[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-23aa47d2cd68400c88d95fc1a3e6dbcc | Cc1nc(N)sc1CCO[N+](=O)[O-].O=C(O)Cc1ccc(Cl)cc1Cl>>Cc1nc(NC(=O)Cc2ccc(Cl)cc2Cl)sc1CCO[N+](=O)[O-] | ClC1=C(C=CC(=C1)Cl)CC(=O)O.CC=1N=C(SC1CCO[N+](=O)[O-])N>>ClC1=C(C=CC(=C1)Cl)CC(=O)NC=1SC(=C(N1)C)CCO[N+](=O)[O-] | [CH3:1][c:2]1[n:3][c:4]([NH2:5])[s:17][c:18]1[CH2:19][CH2:20][O:21][N+:22](=[O:23])[O-:24].O[C:6](=[O:7])[CH2:8][c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]1[Cl:16]>>[CH3:1][c:2]1[n:3][c:4]([NH:5][C:6](=[O:7])[CH2:8][c:9]2[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]2[Cl:16])[s:17][c:18]1[CH2:19][CH2:20][O:21][N+:22](... | Cc1nc(N)sc1CCO[N+](=O)[O-].O=C(O)Cc1ccc(Cl)cc1Cl | Cc1nc(NC(=O)Cc2ccc(Cl)cc2Cl)sc1CCO[N+](=O)[O-] | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccccc1)Nc1nccs1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[NH2;D1;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]-[c:4])-[NH;D2;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1 | 69 | [{"value": 69.0, "product": "ClC1=C(C=CC(=C1)Cl)CC(=O)NC=1SC(=C(N1)C)CCO[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Pet-162 was prepared according to the general procedure described hereinabove and the procedure described above for the preparation of Pet-154, using (2,4-dichloro-phenyl)-acetic acid and 4-methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylamine (Pet-10) as the starting materials, in an overall yield of 69%.
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cscn1.c1ccccc1 | HO- | null | null | null | Cc1nc(N)sc1CCO[N+](=O)[O-].O=C(O)Cc1ccc(Cl)cc1Cl>>Cc1nc(NC(=O)Cc2ccc(Cl)cc2Cl)sc1CCO[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a605c71b084f4c2f97dd5bc977f29a78 | Cc1nc(N)sc1CCO[N+](=O)[O-].O=C(O)COc1ccc(Cl)cc1Cl>>Cc1nc(NC(=O)COc2ccc(Cl)cc2Cl)sc1CCO[N+](=O)[O-] | ClC1=C(OCC(=O)O)C=CC(=C1)Cl.CC=1N=C(SC1CCO[N+](=O)[O-])N>>ClC1=C(OCC(=O)NC=2SC(=C(N2)C)CCO[N+](=O)[O-])C=CC(=C1)Cl | [CH3:1][c:2]1[n:3][c:4]([NH2:5])[s:18][c:19]1[CH2:20][CH2:21][O:22][N+:23](=[O:24])[O-:25].O[C:6](=[O:7])[CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]1[Cl:17]>>[CH3:1][c:2]1[n:3][c:4]([NH:5][C:6](=[O:7])[CH2:8][O:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]2[Cl:17])[s:18][c:19]1[CH2:20][CH2:21][O... | Cc1nc(N)sc1CCO[N+](=O)[O-].O=C(O)COc1ccc(Cl)cc1Cl | Cc1nc(NC(=O)COc2ccc(Cl)cc2Cl)sc1CCO[N+](=O)[O-] | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(COc1ccccc1)Nc1nccs1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#8:4].[NH2;D1;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1>>[#8:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6]1:[#16;a:7]:[c:8]:[c:9]:[#7;a:10]:1 | 77 | [{"value": 77.0, "product": "ClC1=C(OCC(=O)NC=2SC(=C(N2)C)CCO[N+](=O)[O-])C=CC(=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Pet-163 was prepared according to the general procedure described hereinabove and the procedure described above for the preparation of Pet-154, using (2,4-dichloro-phenoxy)-acetic acid and 4-methyl-5-(2-nitrooxy-ethyl)-thiazol-2-ylamine (Pet-10) as the starting materials, in an overall yield of 77%.
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cscn1.c1ccccc1 | HO- | null | null | null | Cc1nc(N)sc1CCO[N+](=O)[O-].O=C(O)COc1ccc(Cl)cc1Cl>>Cc1nc(NC(=O)COc2ccc(Cl)cc2Cl)sc1CCO[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fd8775bd22e142a9814d78f79ee99f8a | COc1ccc(C(=O)Cl)cc1.O=C(O)Cc1cc2ccccc2o1>>COC(=O)Cc1oc2ccccc2c1C(=O)c1ccc(OC)cc1 | C(Cl)Cl.C(Cl)Cl.O1C(=CC2=C1C=CC=C2)CC(=O)O.C(C1=CC=C(C=C1)OC)(=O)Cl.[Sn](Cl)(Cl)(Cl)Cl>>COC(CC=1OC2=C(C1C(C1=CC=C(C=C1)OC)=O)C=CC=C2)=O | Cl[C:15](=[O:16])[c:17]1[cH:18][cH:19][c:20]([O:21][CH3:22])[cH:23][cH:24]1.[OH:2][C:3](=[O:4])[CH2:5][c:6]1[o:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[o:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[c:14]1[C:15](=[O:16])[c:17]1[cH:18][cH:19][c:20]([O:21][CH3:22])[cH:23][c... | COc1ccc(C(=O)Cl)cc1.O=C(O)Cc1cc2ccccc2o1 | COC(=O)Cc1oc2ccccc2c1C(=O)c1ccc(OC)cc1 | null | null | null | C-C Coupling | OtherReaction | dddb846b90c82c349e0f5c6c03fe9fe176df774bdce0504a643fc52d81f035f3 | 3f61ba26fe9791436c27b93d0c669474775a60e3446708a267a9de08824bde1e | O=C(c1ccccc1)c1coc2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[O;D1;H0:6]=[C:7](-[OH;D1;+0:8])-[C:9]-[c:10]1:[#8;a:11]:[c:12](:[c:13]):[c:14](:[c:15]):[cH;D2;+0:16]:1>>[C;D1;H3:17]-[O;H0;D2;+0:8]-[C:7](=[O;D1;H0:6])-[C:9]-[c:10]1:[#8;a:11]:[c:12](:[c:13]):[c:14](:[c:15]):[c;H0;D3;+0:16]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4... | null | [] | 2.5 | CELSIUS | null | null | To the BFAA methyl ester from Step 1 (assumed 1× mole fraction) was added p-anisoyl chloride (approximately 1.08 parts by weight; 1.1× mole fraction), followed by methylene chloride (approximately 3.11 parts by weight). The mixture was stirred and cooled to about 0-5° C. Tin(IV) chloride (approximately 1.46 parts by we... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid | Ketone.Ester | c1ccc2occc2c1 | c1ccc2occc2c1 | c1ccc2occc2c1.c1ccccc1 | null | null | 2.5 | null | COc1ccc(C(=O)Cl)cc1.O=C(O)Cc1cc2ccccc2o1>>COC(=O)Cc1oc2ccccc2c1C(=O)c1ccc(OC)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7ad6453d4cf54be992778f7fe1e383c7 | COc1ccc2c(c1)C(=O)CCC2.N#CCC(=O)O>>COc1ccc2c(c1)C(CC#N)=CCC2 | COC1=CC=C2CCCC(C2=C1)=O.C(#N)CC(=O)O.C(CCCCCC)(=O)O.C(C1=CC=CC=C1)N>>COC1=CC=C2CCC=C(C2=C1)CC#N | O=[C:9]1[c:7]2[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]2)[CH2:15][CH2:14][CH2:13]1.O=C(O)[CH2:10][C:11]#[N:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH2:10][C:11]#[N:12])=[CH:13][CH2:14][CH2:15]2 | COc1ccc2c(c1)C(=O)CCC2.N#CCC(=O)O | COc1ccc2c(c1)C(CC#N)=CCC2 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 3e70e866b98f372e41911525859504a45209e8db64b85e08ca0b480f1563a6d5 | 02013e56752ca1fd9fb0bbdf226e0bfdac2dbd797ed2ed05b3b4588994250c74 | C1=Cc2ccccc2CC1 | O-C(=O)-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].O=[C;H0;D3;+0:4]1-[CH2;D2;+0:5]-[C:6]-[C:7]-[c:8]:[c:9]-1:[c:10]>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[C;H0;D3;+0:4]1=[CH;D2;+0:5]-[C:6]-[C:7]-[c:8]:[c:9]-1:[c:10] | 90 | [{"value": 90.0, "product": "COC1=CC=C2CCC=C(C2=C1)CC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | There are introduced into a 670 litre reactor 85.0 kg of 7-methoxy-1-tetralone, 60.3 kg of cyanoacetic acid and 15.6 kg of heptanoic acid in toluene in the presence of 12.7 kg of benzylamine. The mixture is heated at reflux. When all the starting substrate has disappeared, the solution is cooled and filtered. The preci... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | null | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | HO- | C1(=CC=CC=C1)C | null | null | COc1ccc2c(c1)C(=O)CCC2.N#CCC(=O)O>C1(=CC=CC=C1)C>COc1ccc2c(c1)C(CC#N)=CCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6f3259ed7688457f9829d89572f09c26 | COc1ccc2c(c1)C(CC#N)=CCC2>>COc1ccc2cccc(CC#N)c2c1 | COC1=CC=C2CCC=C(C2=C1)CC#N.C(C(=C)C)(=O)OCC=C>>COC1=CC=C2C=CC=C(C2=C1)CC#N | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:14]([cH:15]1)[C:10]([CH2:11][C:12]#[N:13])=[CH:9][CH2:8][CH2:7]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][C:12]#[N:13])[c:14]2[cH:15]1 | COc1ccc2c(c1)C(CC#N)=CCC2 | COc1ccc2cccc(CC#N)c2c1 | null | [Pd] | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 93b4073d401b9871f39ba19f09d22c2607d954c2113d57f576b8550ecea6c3e1 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2ccccc2c1 | [N;D1;H0:1]#[C:2]-[C:3]-[C;H0;D3;+0:4]1=[CH;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]-1:[c:11]>>[N;D1;H0:1]#[C:2]-[C:3]-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[c:8](:[c:9]):[c:10]:1:[c:11] | 91 | [{"value": 91.0, "product": "COC1=CC=C2C=CC=C(C2=C1)CC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | There are introduced into a 670 litre reactor 12.6 kg of 5% palladium-on-carbon in toluene, which is heated at reflux; then 96.1 kg of (7-methoxy-3,4-dihydro-1-naphthalenyl)-acetonitrile dissolved in toluene are added as well as 63.7 kg of allyl methacrylate. The reaction is continued at reflux and is followed by vapou... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=Cc2ccccc2CC1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | null | [Pd].C1(=CC=CC=C1)C | null | null | COc1ccc2c(c1)C(CC#N)=CCC2>[Pd].C1(=CC=CC=C1)C>COc1ccc2cccc(CC#N)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dd37ef5c614245cf806a221934f95997 | CC(=O)OC(C)=O.COc1ccc2cccc(CCN)c2c1>>COc1ccc2cccc(CCNC(C)=O)c2c1 | O.Cl.COC1=CC=C2C=CC=C(C2=C1)CCN.C(C)(=O)[O-].[Na+].C(C)(=O)OC(C)=O>>COC1=CC=C2C=CC=C(C2=C1)CCNC(C)=O | CC(=O)O[C:14]([CH3:15])=[O:16].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][CH2:12][NH2:13])[c:17]2[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][CH2:12][NH:13][C:14]([CH3:15])=[O:16])[c:17]2[cH:18]1 | CC(=O)OC(C)=O.COc1ccc2cccc(CCN)c2c1 | COc1ccc2cccc(CCNC(C)=O)c2c1 | null | null | C(C)O | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccc2ccccc2c1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 92.5 | [{"value": 92.5, "product": "COC1=CC=C2C=CC=C(C2=C1)CCNC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 173 kg of the compound obtained in Step C and 66 kg of sodium acetate in ethanol are introduced into a 1600 litre reactor. The mixture is stirred and then 79 kg of acetic anhydride are added; the reaction mixture is heated at reflux and 600 l of water are added. The reaction mixture is allowed to return to ambient temp... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccc2ccccc2c1 | HO- | C(C)O | null | null | CC(=O)OC(C)=O.COc1ccc2cccc(CCN)c2c1>C(C)O>COc1ccc2cccc(CCNC(C)=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-65669adb17ce443999a3c4154bfe5e13 | COc1ccc2c(c1)C(=O)CCC2.N#CCC(=O)O>>COc1ccc2c(c1)C(CC#N)=CCC2 | COC1=CC=C2CCCC(C2=C1)=O.C(#N)CC(=O)O.C(CCCCCC)(=O)O.NC1=CC=CC=C1>>COC1=CC=C2CCC=C(C2=C1)CC#N | O=[C:9]1[c:7]2[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]2)[CH2:15][CH2:14][CH2:13]1.O=C(O)[CH2:10][C:11]#[N:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH2:10][C:11]#[N:12])=[CH:13][CH2:14][CH2:15]2 | COc1ccc2c(c1)C(=O)CCC2.N#CCC(=O)O | COc1ccc2c(c1)C(CC#N)=CCC2 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 3e70e866b98f372e41911525859504a45209e8db64b85e08ca0b480f1563a6d5 | 02013e56752ca1fd9fb0bbdf226e0bfdac2dbd797ed2ed05b3b4588994250c74 | C1=Cc2ccccc2CC1 | O-C(=O)-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].O=[C;H0;D3;+0:4]1-[CH2;D2;+0:5]-[C:6]-[C:7]-[c:8]:[c:9]-1:[c:10]>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[C;H0;D3;+0:4]1=[CH;D2;+0:5]-[C:6]-[C:7]-[c:8]:[c:9]-1:[c:10] | 87 | [{"value": 87.0, "product": "COC1=CC=C2CCC=C(C2=C1)CC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | There are introduced into a 670 litre reactor 85.0 kg of 7-methoxy-1-tetralone, 60.3 kg of cyanoacetic acid and 15.6 kg of heptanoic acid in toluene in the presence of 11.0 kg of aniline. The mixture is heated at reflux. When all the starting substrate has disappeared, the solution is cooled and filtered. The precipita... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | null | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | HO- | C1(=CC=CC=C1)C | null | null | COc1ccc2c(c1)C(=O)CCC2.N#CCC(=O)O>C1(=CC=CC=C1)C>COc1ccc2c(c1)C(CC#N)=CCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-58e68d6ece3f454f9dbd51ec8dde8f80 | COc1ccc2c(c1)C(=O)CCC2.N#CCC(=O)O>>COc1ccc2c(c1)C(CC#N)=CCC2 | COC1=CC=C2CCCC(C2=C1)=O.C(#N)CC(=O)O.C(CCCCCC)(=O)O.C(C1=CC=CC=C1)N>>COC1=CC=C2CCC=C(C2=C1)CC#N | O=[C:9]1[c:7]2[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]2)[CH2:15][CH2:14][CH2:13]1.O=C(O)[CH2:10][C:11]#[N:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH2:10][C:11]#[N:12])=[CH:13][CH2:14][CH2:15]2 | COc1ccc2c(c1)C(=O)CCC2.N#CCC(=O)O | COc1ccc2c(c1)C(CC#N)=CCC2 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 3e70e866b98f372e41911525859504a45209e8db64b85e08ca0b480f1563a6d5 | 02013e56752ca1fd9fb0bbdf226e0bfdac2dbd797ed2ed05b3b4588994250c74 | C1=Cc2ccccc2CC1 | O-C(=O)-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].O=[C;H0;D3;+0:4]1-[CH2;D2;+0:5]-[C:6]-[C:7]-[c:8]:[c:9]-1:[c:10]>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[C;H0;D3;+0:4]1=[CH;D2;+0:5]-[C:6]-[C:7]-[c:8]:[c:9]-1:[c:10] | 90 | [{"value": 90.0, "product": "COC1=CC=C2CCC=C(C2=C1)CC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | There are introduced into a 670 liter reactor 85.0 kg of 7-methoxy-1-tetralone, 60.3 kg of cyanoacetic acid and 15.6 kg of heptanoic acid in toluene in the presence of 12.7 kg of benzylamine. The mixture is heated at reflux. When all the starting substrate has disappeared, the solution is cooled and filtered. The preci... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | null | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | HO- | C1(=CC=CC=C1)C | null | null | COc1ccc2c(c1)C(=O)CCC2.N#CCC(=O)O>C1(=CC=CC=C1)C>COc1ccc2c(c1)C(CC#N)=CCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c291f4ccf332430e8bb9d2beee8ef59b | COc1ccc2c(c1)C(CC#N)=CCC2>>COc1ccc2cccc(CC#N)c2c1 | COC1=CC=C2CCC=C(C2=C1)CC#N.C(C(=C)C)(=O)OCC=C>>COC1=CC=C2C=CC=C(C2=C1)CC#N | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:14]([cH:15]1)[C:10]([CH2:11][C:12]#[N:13])=[CH:9][CH2:8][CH2:7]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][C:12]#[N:13])[c:14]2[cH:15]1 | COc1ccc2c(c1)C(CC#N)=CCC2 | COc1ccc2cccc(CC#N)c2c1 | null | [Pd] | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 93b4073d401b9871f39ba19f09d22c2607d954c2113d57f576b8550ecea6c3e1 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc2ccccc2c1 | [N;D1;H0:1]#[C:2]-[C:3]-[C;H0;D3;+0:4]1=[CH;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]-1:[c:11]>>[N;D1;H0:1]#[C:2]-[C:3]-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[c:8](:[c:9]):[c:10]:1:[c:11] | 91 | [{"value": 91.0, "product": "COC1=CC=C2C=CC=C(C2=C1)CC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | There are introduced into a 670 liter reactor 12.6 kg of 5% palladium-on-carbon in toluene, which is heated at reflux; then 96.1 kg of (7-methoxy-3,4-dihydro-1-naphthalenyl)-acetonitrile dissolved in toluene are added as well as 63.7 kg of allyl methacrylate. The reaction is continued at reflux and is followed by vapou... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=Cc2ccccc2CC1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | null | [Pd].C1(=CC=CC=C1)C | null | null | COc1ccc2c(c1)C(CC#N)=CCC2>[Pd].C1(=CC=CC=C1)C>COc1ccc2cccc(CC#N)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-622244ec24d0411ab05fdf9ec7365129 | CC(=O)OC(C)=O.COc1ccc2cccc(CCN)c2c1>>COc1ccc2cccc(CCNC(C)=O)c2c1 | O.Cl.COC1=CC=C2C=CC=C(C2=C1)CCN.C(C)(=O)[O-].[Na+].C(C)(=O)OC(C)=O>>COC1=CC=C2C=CC=C(C2=C1)CCNC(C)=O | CC(=O)O[C:14]([CH3:15])=[O:16].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][CH2:12][NH2:13])[c:17]2[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([CH2:11][CH2:12][NH:13][C:14]([CH3:15])=[O:16])[c:17]2[cH:18]1 | CC(=O)OC(C)=O.COc1ccc2cccc(CCN)c2c1 | COc1ccc2cccc(CCNC(C)=O)c2c1 | null | null | C(C)O | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccc2ccccc2c1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 92.5 | [{"value": 92.5, "product": "COC1=CC=C2C=CC=C(C2=C1)CCNC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 173 kg of the compound obtained in Step C and 66 kg of sodium acetate in ethanol are introduced into a 1600 liter reactor. The mixture is stirred and then 79 kg of acetic anhydride are added; the reaction mixture is heated at reflux and 600 l of water are added. The reaction mixture is allowed to return to ambient temp... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccc2ccccc2c1 | HO- | C(C)O | null | null | CC(=O)OC(C)=O.COc1ccc2cccc(CCN)c2c1>C(C)O>COc1ccc2cccc(CCNC(C)=O)c2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2618a2fa553c4f2da02bd9a7282f33f1 | COc1ccc2c(c1)C(=O)CCC2.N#CCC(=O)O>>COc1ccc2c(c1)C(CC#N)=CCC2 | COC1=CC=C2CCCC(C2=C1)=O.C(#N)CC(=O)O.C(CCCCCC)(=O)O.NC1=CC=CC=C1>>COC1=CC=C2CCC=C(C2=C1)CC#N | O=[C:9]1[c:7]2[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]2)[CH2:15][CH2:14][CH2:13]1.O=C(O)[CH2:10][C:11]#[N:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH2:10][C:11]#[N:12])=[CH:13][CH2:14][CH2:15]2 | COc1ccc2c(c1)C(=O)CCC2.N#CCC(=O)O | COc1ccc2c(c1)C(CC#N)=CCC2 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 3e70e866b98f372e41911525859504a45209e8db64b85e08ca0b480f1563a6d5 | 02013e56752ca1fd9fb0bbdf226e0bfdac2dbd797ed2ed05b3b4588994250c74 | C1=Cc2ccccc2CC1 | O-C(=O)-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].O=[C;H0;D3;+0:4]1-[CH2;D2;+0:5]-[C:6]-[C:7]-[c:8]:[c:9]-1:[c:10]>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[C;H0;D3;+0:4]1=[CH;D2;+0:5]-[C:6]-[C:7]-[c:8]:[c:9]-1:[c:10] | 87 | [{"value": 87.0, "product": "COC1=CC=C2CCC=C(C2=C1)CC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | There are introduced into a 670 liter reactor 85.0 kg of 7-methoxy-1-tetralone, 60.3 kg of cyanoacetic acid and 15.6 kg of heptanoic acid in toluene in the presence of 11.0 kg of aniline. The mixture is heated at reflux. When all the starting substrate has disappeared, the solution is cooled and filtered. The precipita... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | null | c1ccc2c(c1)CCCC2 | C1=Cc2ccccc2CC1 | C1=Cc2ccccc2CC1 | HO- | C1(=CC=CC=C1)C | null | null | COc1ccc2c(c1)C(=O)CCC2.N#CCC(=O)O>C1(=CC=CC=C1)C>COc1ccc2c(c1)C(CC#N)=CCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-25599238006d4dc4b25790d8a0361922 | CC(C)I.Nc1ccccc1O>>CC(C)Nc1ccccc1O | IC(C)C.NC1=C(C=CC=C1)O.CN(C=O)C>>C(C)(C)NC1=C(C=CC=C1)O | I[CH:2]([CH3:1])[CH3:3].[NH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[OH:11]>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[OH:11] | CC(C)I.Nc1ccccc1O | CC(C)Nc1ccccc1O | null | C(O)([O-])=O.[K+] | O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | f34cfd111cb1c313e466b6e38dbeced3d9899f24c77e1e239b4fdfffb1642baf | f727fed8b2cf723a92e5af137ab57c7229fb353af6a01a0b7b0aeb3a7b28a8b4 | c1ccccc1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Into a 100 mL flask purged with nitrogen were added 12 g (109.92 mmol) of o-aminophenol and 60 mL of dimethylformamide (DMF), and the resultant mixture was stirred at room temperature and dissolved. Then, the obtained solution was mixed with 22.4 g (132 mmol) of 2-iodopropane such (molar ratio of 2-iodopropane to o-ami... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary amine | Secondary amine | null | null | c1ccccc1 | HI | C(O)([O-])=O.[K+].O | null | null | CC(C)I.Nc1ccccc1O>C(O)([O-])=O.[K+].O>CC(C)Nc1ccccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5fdff8ad94b1459fb6ebc4bbffce679d | CC(C)I.Nc1ccccc1O>>CC(C)Nc1ccccc1O | IC(C)C.NC1=C(C=CC=C1)O.IC(C)C>>C(C)(C)NC1=C(C=CC=C1)O | I[CH:2]([CH3:1])[CH3:3].[NH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[OH:11]>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[OH:11] | CC(C)I.Nc1ccccc1O | CC(C)Nc1ccccc1O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | f34cfd111cb1c313e466b6e38dbeced3d9899f24c77e1e239b4fdfffb1642baf | f727fed8b2cf723a92e5af137ab57c7229fb353af6a01a0b7b0aeb3a7b28a8b4 | c1ccccc1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 2 | HOUR | The same procedure as in Example 1 was repeated except that the molar ratio of 2-iodopropane to o-aminophenol was changed to 1.0, the 2-iodopropane was dropped over 3 h, and then the reaction mixture was stirred at room temperature for 2 h.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary amine | Secondary amine | null | null | c1ccccc1 | HI | null | null | 2 | CC(C)I.Nc1ccccc1O>>CC(C)Nc1ccccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a66bff23406847e9a3334b516b0044ad | CC(C)=O.Nc1ccccc1O>>CC(C)Nc1ccccc1O | NC1=C(C=CC=C1)O.CC(=O)C.[O-]S(=O)(=O)[O-].[Mg+2]>>C(C)(C)NC1=C(C=CC=C1)O | O=[C:2]([CH3:1])[CH3:3].[NH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[OH:11]>>[CH3:1][CH:2]([CH3:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[OH:11] | CC(C)=O.Nc1ccccc1O | CC(C)Nc1ccccc1O | null | [Pd] | null | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 100 | CELSIUS | null | null | Into a 300 mL autoclave were charged 12 g (109.92 mmol) of o-aminophenol, 100 mL (79 g; 1.4 mol) of acetone, 0.6 g of Pd/C (Pd content: 5% by mass) and 30 g of MgSO4, and the contents of the autoclave were heated at 100° C. while stirring under a hydrogen pressure of 1.0 MPa. After the elapse of 1 h, the hydrogen absor... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1 | Other | [Pd] | 100 | null | CC(C)=O.Nc1ccccc1O>[Pd]>CC(C)Nc1ccccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a4f48cb693294aaea3c29805e7a8377b | CCCCC(C)I.Nc1ccccc1O>>CCCCC(C)Nc1ccccc1O | IC(C)CCCC.NC1=C(C=CC=C1)O>>CC(CCCC)NC1=C(C=CC=C1)O | I[CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH3:6].[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14] | CCCCC(C)I.Nc1ccccc1O | CCCCC(C)Nc1ccccc1O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | f34cfd111cb1c313e466b6e38dbeced3d9899f24c77e1e239b4fdfffb1642baf | f727fed8b2cf723a92e5af137ab57c7229fb353af6a01a0b7b0aeb3a7b28a8b4 | c1ccccc1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 320 | MINUTE | The same procedure as in Example 4 was repeated except for using 2-iodohexane in place of 2-iodobutane, to conduct the reaction. As a result, it was confirmed that the rate of conversion of o-aminophenol was 93%, the selectivity to the N-monoalkylated compound was 41% and the oxygen absorption initiation time as an ind... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary amine | Secondary amine | null | null | c1ccccc1 | HI | null | null | 5.333333 | CCCCC(C)I.Nc1ccccc1O>>CCCCC(C)Nc1ccccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-25de0d922c614920bc11e2d755fc570c | CCCCC(C)I.Nc1ccccc1O>>CCCCC(C)Nc1ccccc1O | NC1=C(C=CC=C1)O.IC(C)CCCC.NC1=C(C=CC=C1)O.IC(C)CCCC>>CC(CCCC)NC1=C(C=CC=C1)O | I[CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH3:6].[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14] | CCCCC(C)I.Nc1ccccc1O | CCCCC(C)Nc1ccccc1O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | f34cfd111cb1c313e466b6e38dbeced3d9899f24c77e1e239b4fdfffb1642baf | f727fed8b2cf723a92e5af137ab57c7229fb353af6a01a0b7b0aeb3a7b28a8b4 | c1ccccc1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 0.5 | HOUR | The same procedure as in Example 6 was repeated except that the molar ratio of 2-iodohexane to o-aminophenol was changed to 0.8, the 2-iodohexane was dropped over 4.5 h, and then the reaction mixture was stirred at room temperature for 0.5 h. As a result, it was confirmed that the rate of conversion of o-aminophenol wa... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Primary amine | Secondary amine | null | null | c1ccccc1 | HI | null | null | 0.5 | CCCCC(C)I.Nc1ccccc1O>>CCCCC(C)Nc1ccccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-15517788c82a494ab29657e4fdbb073d | CCCCC(C)=O.Nc1ccccc1O>>CCCCC(C)Nc1ccccc1O | CC(CCCC)=O.NC1=C(C=CC=C1)O>>CC(CCCC)NC1=C(C=CC=C1)O | O=[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH3:6].[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14] | CCCCC(C)=O.Nc1ccccc1O | CCCCC(C)Nc1ccccc1O | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[CH;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 320 | MINUTE | The same procedure as in Example 3 was repeated except for using 145 mL (121 g; 1.2 mol) of 2-hexanone in place of 100 mL of acetone, to conduct the reaction. As a result, it was confirmed that the rate of conversion of o-aminophenol was 93%, the selectivity to the N-monoalkylated compound (molar ratio of the monoalkyl... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | c1ccccc1 | Other | null | null | 5.333333 | CCCCC(C)=O.Nc1ccccc1O>>CCCCC(C)Nc1ccccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b3d9903ac92242edb1c9ff9725e0d4ba | CCOC(=O)c1c(C)cc(Cl)nc1C>>Cc1cc(Cl)nc(C)c1C(=O)O | C(C)OC(C1=C(N=C(C=C1C)Cl)C)=O.[OH-].[Na+]>>ClC1=NC(=C(C(=O)O)C(=C1)C)C | CC[O:12][C:10]([c:9]1[c:2]([CH3:1])[cH:3][c:4]([Cl:5])[n:6][c:7]1[CH3:8])=[O:11]>>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[n:6][c:7]([CH3:8])[c:9]1[C:10](=[O:11])[OH:12] | CCOC(=O)c1c(C)cc(Cl)nc1C | Cc1cc(Cl)nc(C)c1C(=O)O | null | null | CCO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | 90 | CELSIUS | null | null | To a solution of 6-chloro-2,4-dimethyl-nicotinic acid ethyl ester (0.200 g, 0.930 mmol) in EtOH (1 mL) was added 4N NaOH (1 mL), and the mixture was heated at 90° C. for 1 h. After the mixture was cooled to room temperature EtOH was removed and the aqueous residue was acidified with 4N HCl to afford a white precipitate... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | Other | CCO | 90 | null | CCOC(=O)c1c(C)cc(Cl)nc1C>CCO>Cc1cc(Cl)nc(C)c1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-855c69ff66e3428d9430d67f6fe34fc3 | Cc1cc(N)nc(C)c1Br>>Cc1cc(F)nc(C)c1Br | NC1=NC(=C(C(=C1)C)Br)C.[H+].[B-](F)(F)(F)F.N(=O)[O-].[Na+]>>BrC=1C(=NC(=CC1C)F)C | N[c:4]1[cH:3][c:2]([CH3:1])[c:9]([Br:10])[c:7]([CH3:8])[n:6]1>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[n:6][c:7]([CH3:8])[c:9]1[Br:10] | Cc1cc(N)nc(C)c1Br | Cc1cc(F)nc(C)c1Br | null | null | O | Functional Group Interconversion | Primary amine to fluoride | c34356dee62682a5768cf6d77cd41509a1ca5fa7825c2ccee4407118d8ca7dbf | 9c224743a26d9e1c3135e4817dd611aec414d8ea156f02200a3aef865be78b01 | c1ccncc1 | N-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]>>[F;D1;H0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 36 | [{"value": 36.0, "product": "BrC=1C(=NC(=CC1C)F)C", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a suspension of 2-amino-5-bromo-4,6-dimethylpyridine (4.02 g, 20.0 mmol) in HBF4 (48% in water, 15 mL) cooled in an ice bath was added a solution of NaNO2 (1.73 g, 25.0 mmol) in water (5 mL). The reaction mixture turned clear, and 10 min later a precipitate was formed. The precipitate was collected by filtration, dr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | null | O | 90 | null | Cc1cc(N)nc(C)c1Br>O>Cc1cc(F)nc(C)c1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-530c13a757684a41ba0314864b7f377d | Cc1cc(F)nc(C)c1Br.O=C=O>>Cc1cc(F)nc(C)c1C(=O)O | C(=O)=O.BrC=1C(=NC(=CC1C)F)C.[Li]C(C)(C)C>>FC1=NC(=C(C(=O)O)C(=C1)C)C | Br[c:9]1[c:2]([CH3:1])[cH:3][c:4]([F:5])[n:6][c:7]1[CH3:8].[C:10](=[O:11])=[O:12]>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[n:6][c:7]([CH3:8])[c:9]1[C:10](=[O:11])[OH:12] | Cc1cc(F)nc(C)c1Br.O=C=O | Cc1cc(F)nc(C)c1C(=O)O | null | null | CCOCC | Acylation | OtherReaction | bc92cead4aa97e1764a195240ff3da90b47308e1f3e7797c5e074724c9e4e7cd | d0d963f3850574b1f0fda744314036458b2dd627cb0c4e2f893b9c52a88ad449 | c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2](-[C;D1;H3:3]):[c:4]:[c:5]:[#7;a:6]:[c:7]:1-[C;D1;H3:8].[O;D1;H0:9]=[C;H0;D2;+0:10]=[O;H0;D1;+0:11]>>[C;D1;H3:3]-[c:2]1:[c:4]:[c:5]:[#7;a:6]:[c:7](-[C;D1;H3:8]):[c;H0;D3;+0:1]:1-[C;H0;D3;+0:10](=[O;D1;H0:9])-[OH;D1;+0:11] | 73 | [{"value": 73.0, "product": "FC1=NC(=C(C(=O)O)C(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 10 | MINUTE | To a solution of 3-bromo-2,4-dimethyl-6-fluoropyridine (1.45 g, 7.10 mmol) in anhydrous Et2O (25 mL) at −78° C. was added t-BuLi (1.7M in pentane, 8.8 mL, 15 mmol) dropwise. After addition the mixture was stirred at −78° C. for 10 min, and CO2 was introduced. After 10 min the cooling bath was removed, and the bubbling ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbon dioxide | Carboxylic acid | c1ccncc1 | c1ccncc1 | c1ccncc1 | Br- | CCOCC | -78 | 0.166667 | Cc1cc(F)nc(C)c1Br.O=C=O>CCOCC>Cc1cc(F)nc(C)c1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0f1ac2612a434355a73f01bff15bcbfa | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1cc(Cl)nc(C)c1C(=O)O>>COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(Cl)nc3C)CC2)cc1 | NCC[C@@H](C)N1CCC(CC1)N(CC=1C=NC=CC1C)C1=CC=C(C=C1)OC.ClC1=NC(=C(C(=O)O)C(=C1)C)C.C=1C=CC2=C(C1)N=NN2O.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>>ClC1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=C1)C)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH2:8][c:9]2[cH:10][n:11][cH:12][cH:13][c:14]2[CH3:15])[CH:16]2[CH2:17][CH2:18][N:19]([C@H:20]([CH3:21])[CH2:22][CH2:23][NH2:24])[CH2:36][CH2:37]2)[cH:38][cH:39]1.O[C:25](=[O:26])[c:27]1[c:28]([CH3:29])[cH:30][c:31]([Cl:32])[n:33][c:34]1[CH3:35]>>[CH3:1][O:2][c:3]1[cH:4][cH:5]... | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1cc(Cl)nc(C)c1C(=O)O | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(Cl)nc3C)CC2)cc1 | null | null | [Cl-].[Na+].O.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCN1CCC(N(Cc2cccnc2)c2ccccc2)CC1)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8] | 80 | [{"value": 80.0, "product": "ClC1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.0, "product": "ClC1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | null | null | To a solution of [1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-(4-methoxy-phenyl)-(4-methyl-pyridin-3-ylmethyl)-amine (63 mg, 0.17 mmol) in DMF (1.5 mL) was added 6-chloro-2,4-dimethyl-nicotinic acid (40 mg, 0.22 mmol), HOBT (31 mg, 0.23 mmol), EDCI (44 mg, 0.23 mmol) and DIPEA (85 μL, 0.50 mmol). After the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HO- | [Cl-].[Na+].O.CN(C)C=O | null | null | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1cc(Cl)nc(C)c1C(=O)O>[Cl-].[Na+].O.CN(C)C=O>COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(Cl)nc3C)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8b45e0d9f49947e4994e06da3272a1f0 | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1cc(C#N)cc(C)c1C(=O)O>>COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C#N)cc3C)CC2)cc1 | C(#N)C1=CC(=C(C(=O)O)C(=C1)C)C.NCC[C@@H](C)N1CCC(CC1)N(CC=1C=NC=CC1C)C1=CC=C(C=C1)OC.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.C=1C=CC2=C(C1)N=NN2O>>C(#N)C1=CC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=C1)C)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH2:8][c:9]2[cH:10][n:11][cH:12][cH:13][c:14]2[CH3:15])[CH:16]2[CH2:17][CH2:18][N:19]([C@H:20]([CH3:21])[CH2:22][CH2:23][NH2:24])[CH2:37][CH2:38]2)[cH:39][cH:40]1.O[C:25](=[O:26])[c:27]1[c:28]([CH3:29])[cH:30][c:31]([C:32]#[N:33])[cH:34][c:35]1[CH3:36]>>[CH3:1][O:2][c:3]1[cH:4... | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1cc(C#N)cc(C)c1C(=O)O | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C#N)cc3C)CC2)cc1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCN1CCC(N(Cc2cccnc2)c2ccccc2)CC1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 54.5 | [{"value": 54.0, "product": "C(#N)C1=CC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.5, "product": "C(#N)C1=CC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_des... | 25 | CELSIUS | 16 | HOUR | (R)-[1-(3-Amino-1-methyl-propyl)-piperidin-4-yl]-(4-methoxy-phenyl)-(4-methyl-pyridin-3-ylmethyl)-amine (1.00 g, 2.62 mmol), EDCI (0.55 g, 2.88 mmol) and HOBT (0.39 g, 2.88 mmol) were combined in DMF (5 mL) to give a pale yellow solution. To this solution was added 4-cyano-2,6-dimethyl-benzoic acid (0.50 g, 2.88 mmol) ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccccc1 | HO- | CN(C)C=O | 25 | 16 | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1cc(C#N)cc(C)c1C(=O)O>CN(C)C=O>COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C#N)cc3C)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dd8a94e5895843958893a72fbcce13a9 | CNC.COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C(=O)O)cc3C)CC2)cc1>>COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C(=O)N(C)C)cc3C)CC2)cc1 | CNC.COC1=CC=C(C=C1)N(C1CCN(CC1)[C@@H](CCNC(C1=C(C=C(C(=O)O)C=C1C)C)=O)C)CC=1C=NC=CC1C.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.C=1C=CC2=C(C1)N=NN2O>>COC1=CC=C(C=C1)N(C1CCN(CC1)[C@@H](CCNC(C1=C(C=C(C(=O)N(C)C)C=C1C)C)=O)C)CC=1C=NC=CC1C | [NH:34]([CH3:35])[CH3:36].O[C:32]([c:31]1[cH:30][c:28]([CH3:29])[c:27]([C:25]([NH:24][CH2:23][CH2:22][C@H:20]([N:19]2[CH2:18][CH2:17][CH:16]([N:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:43][cH:42]3)[CH2:8][c:9]3[cH:10][n:11][cH:12][cH:13][c:14]3[CH3:15])[CH2:41][CH2:40]2)[CH3:21])=[O:26])[c:38]([CH3:39])[cH:37]1)=[O:... | CNC.COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C(=O)O)cc3C)CC2)cc1 | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C(=O)N(C)C)cc3C)CC2)cc1 | null | null | CN(C)C=O | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(NCCCN1CCC(N(Cc2cccnc2)c2ccccc2)CC1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[C;D1;H3:6]-[N;H0;D3;+0:7](-[C;D1;H3:8])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 39.8 | [{"value": 38.0, "product": "COC1=CC=C(C=C1)N(C1CCN(CC1)[C@@H](CCNC(C1=C(C=C(C(=O)N(C)C)C=C1C)C)=O)C)CC=1C=NC=CC1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.8, "product": "COC1=CC=C(C=C1)N(C1CCN(CC1)[C@@H](CCNC(C1=C(C=C(C(=O)N(C)C)C=C1C)C)=O)C)CC=1C=NC=CC1C", "details": "CALCULATEDPERCENTYIELD", "... | 25 | CELSIUS | 16 | HOUR | N-((R)-3-{4-[(4-Methoxy-phenyl)-(4-methyl-pyridin-3-ylmethyl)-amino]-piperidin-1-yl}-butyl)-3,5-dimethyl-terephthalamic acid (0.070 g, 0.12 mmol), EDCI (0.026 g, 0.13 mmol) and HOBT (0.019 g, 0.13 mmol) were combined in DMF (5 mL) to give a pale yellow solution. To this solution was added dimethylamine (2M in THF) (94 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccccc1 | HO- | CN(C)C=O | 25 | 16 | CNC.COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C(=O)O)cc3C)CC2)cc1>CN(C)C=O>COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C(=O)N(C)C)cc3C)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ddec1011fa542afb37a6fbc35319775 | C1CCOC1.CCN(C(C)C)C(C)C.COc1ccc(NC2CCN([C@H](C)CC#N)CC2)cc1>>COc1ccc(N(C(=O)c2cccnc2)C2CCN([C@H](C)CC#N)CC2)cc1 | COC1=CC=C(C=C1)NC1CCN(CC1)[C@@H](CC#N)C.CCN(C(C)C)C(C)C.C1CCOC1.C1CCOC1>>C(#N)C[C@@H](C)N1CCC(CC1)N(C(C1=CN=CC=C1)=O)C1=CC=C(C=C1)OC | [CH2:8]1[O:9][CH2:12][CH2:11][CH2:10]1.CC(C)[N:14]([CH:13](C)C)[CH2:15]C.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH:16]2[CH2:17][CH2:18][N:19]([C@H:20]([CH3:21])[CH2:22][C:23]#[N:24])[CH2:25][CH2:26]2)[cH:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][n:14][cH:15]2)[... | C1CCOC1.CCN(C(C)C)C(C)C.COc1ccc(NC2CCN([C@H](C)CC#N)CC2)cc1 | COc1ccc(N(C(=O)c2cccnc2)C2CCN([C@H](C)CC#N)CC2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 37940746f39442a9c99391a0cb033567cba8352cc93b35de95626b3248c780e8 | ed98d6b0d01b684eb61d4d1ba8fff62b10cbb8e0a3ae4422806c42e57a843ad5 | O=C(c1cccnc1)N(c1ccccc1)C1CCNCC1 | C-[CH2;D2;+0:1]-[N;H0;D3;+0:2](-C(-C)-C)-[CH;D3;+0:3](-C)-C.[CH2;D2;+0:4]1-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:8]-1.[C:9]-[C:10](-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[C:15]>>[C:9]-[C:10](-[N;H0;D3;+0:11](-[C;H0;D3;+0:8](=[O;H0;D1;+0:7])-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:3]:[n;H0;D2... | 81 | [{"value": 81.0, "product": "C(#N)C[C@@H](C)N1CCC(CC1)N(C(C1=CN=CC=C1)=O)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | The residue was suspended in THF (30 mL) and cooled to 0° C. A solution of (R)-3-[4-(4-methoxy-phenylamino)-piperidin-1-yl]-butyronitrile (1.09 g, 1 eq.) and DIPEA (1.5 mL, 2 eq.) in THF (10 mL) was added drop-wise and the mixture was stirred at 0° C. for 30 min. The reaction was quenched with saturated NaHCO3 (50 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine.Tertiary amine | Tertiary amide | C1CCOC1 | c1ccncc1 | c1ccccc1.c1ccncc1.C1CC[NH]CC1 | Other | null | 0 | 0.5 | C1CCOC1.CCN(C(C)C)C(C)C.COc1ccc(NC2CCN([C@H](C)CC#N)CC2)cc1>>COc1ccc(N(C(=O)c2cccnc2)C2CCN([C@H](C)CC#N)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-faa93dd4e7334d8b9a9238aa79125fb0 | COc1ccc(N(Cc2cccnc2)C2CCN([C@H](C)CCN)CC2)cc1.Cc1cc(Cl)nc(C)c1C(=O)O>>COc1ccc(N(Cc2cccnc2)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(Cl)nc3C)CC2)cc1 | ClC1=NC(=C(C(=O)O)C(=C1)C)C.C=1C=CC2=C(C1)N=NN2O.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.NCC[C@@H](C)N1CCC(CC1)N(CC=1C=NC=CC1)C1=CC=C(C=C1)OC>>ClC1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2)C2=CC=C(C=C2)OC)C(=C1)C)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][n:13][cH:14]2)[CH:15]2[CH2:16][CH2:17][N:18]([C@H:19]([CH3:20])[CH2:21][CH2:22][NH2:23])[CH2:35][CH2:36]2)[cH:37][cH:38]1.O[C:24](=[O:25])[c:26]1[c:27]([CH3:28])[cH:29][c:30]([Cl:31])[n:32][c:33]1[CH3:34]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([... | COc1ccc(N(Cc2cccnc2)C2CCN([C@H](C)CCN)CC2)cc1.Cc1cc(Cl)nc(C)c1C(=O)O | COc1ccc(N(Cc2cccnc2)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(Cl)nc3C)CC2)cc1 | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCN1CCC(N(Cc2cccnc2)c2ccccc2)CC1)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8] | 77.4 | [{"value": 77.0, "product": "ClC1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2)C2=CC=C(C=C2)OC)C(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.4, "product": "ClC1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2)C2=CC=C(C=C2)OC)C(=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | 6 | HOUR | (R)-[1-(3-Amino-1-methyl-propyl)-piperidin-4-yl]-(4-methoxy-phenyl)-pyridin-3-ylmethyl-amine (0.78 g, 2.12 mmol) was dissolved in DCM (10 mL). 6-Chloro-2,4-dimethyl-nicotinic acid (474 mg, 1.2 eq.), HOBT (430 mg, 1.5 eq.), DIPEA (760 μL, 2 eq.), and EDCI (612 mg, 1.5 eq.) were added sequentially. The mixture was stirre... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HO- | C(Cl)Cl | null | 6 | COc1ccc(N(Cc2cccnc2)C2CCN([C@H](C)CCN)CC2)cc1.Cc1cc(Cl)nc(C)c1C(=O)O>C(Cl)Cl>COc1ccc(N(Cc2cccnc2)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(Cl)nc3C)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c143259a8be47e1b953409dffc4771d | CC(C)N.COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C(=O)O)cc3C)CC2)cc1>>COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C(=O)NC(C)C)cc3C)CC2)cc1 | C(C)(C)N.COC1=CC=C(C=C1)N(C1CCN(CC1)[C@@H](CCNC(C1=C(C=C(C(=O)O)C=C1C)C)=O)C)CC=1C=NC=CC1C.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.C=1C=CC2=C(C1)N=NN2O>>C(C)(C)NC(C1=CC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=C1)C)C)=O | [NH2:34][CH:35]([CH3:36])[CH3:37].O[C:32]([c:31]1[cH:30][c:28]([CH3:29])[c:27]([C:25]([NH:24][CH2:23][CH2:22][C@H:20]([N:19]2[CH2:18][CH2:17][CH:16]([N:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:44][cH:43]3)[CH2:8][c:9]3[cH:10][n:11][cH:12][cH:13][c:14]3[CH3:15])[CH2:42][CH2:41]2)[CH3:21])=[O:26])[c:39]([CH3:40])[cH:3... | CC(C)N.COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C(=O)O)cc3C)CC2)cc1 | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C(=O)NC(C)C)cc3C)CC2)cc1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCN1CCC(N(Cc2cccnc2)c2ccccc2)CC1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[NH2;D1;+0:9]>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 86 | [{"value": 86.0, "product": "C(C)(C)NC(C1=CC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=C1)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.2, "product": "C(C)(C)NC(C1=CC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=C1)C)C)=O", "details": "CALCULATEDPERCEN... | 25 | CELSIUS | 16 | HOUR | N-((R)-3-{4-[(4-Methoxy-phenyl)-(4-methyl-pyridin-3-ylmethyl)-amino]-piperidin-1-yl}-butyl)-3,5-dimethyl-terephthalamic acid (0.050 g, 0.09 mmol), EDCI (0.019 g, 0.10 mmol) and HOBT (0.013 g, 0.10 mmol) were combined in DMF (5 mL) to give a pale yellow solution. To this solution was added isopropylamine (8 μL, 0.10 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccccc1 | HO- | CN(C)C=O | 25 | 16 | CC(C)N.COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C(=O)O)cc3C)CC2)cc1>CN(C)C=O>COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C(=O)NC(C)C)cc3C)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eafe50b759a641cfb474d19673f6e6eb | Cc1ccncc1C(=O)N(c1ccccc1)C1CCN([C@H](C)CC#N)CC1>>CO.Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCN)CC1.[NH4+].[OH-] | C(#N)C[C@@H](C)N1CCC(CC1)N(C(C1=CN=CC=C1C)=O)C1=CC=CC=C1.B.C1CCOC1>>CO.[NH4+].[OH-].NCC[C@@H](C)N1CCC(CC1)N(C1=CC=CC=C1)CC=1C=NC=CC1C | [CH3:3][c:4]1[cH:5][cH:6][n:7][cH:8][c:9]1[C:10]([N:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH:18]1[CH2:19][CH2:20][N:21]([C@H:22]([CH3:23])[CH2:24][C:25]#[N:26])[CH2:27][CH2:28]1)=[O:30]>>[CH3:1][OH:2].[CH3:3][c:4]1[cH:5][cH:6][n:7][cH:8][c:9]1[CH2:10][N:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[CH:18]... | Cc1ccncc1C(=O)N(c1ccccc1)C1CCN([C@H](C)CC#N)CC1 | CO.Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCN)CC1.[NH4+].[OH-] | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 22af2bea14d1cf545d28d9de9d4f225c4d7e76fe00dafaab9091df604db5de29 | e1d4af03a260be819cb21246909cc71b64110f879d6772c5c014369d46fd26b9 | c1ccc(N(Cc2cccnc2)C2CCNCC2)cc1 | [C:1]-[#7:2](-[c:3])-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10].[C:11]-[C:12]-[C;H0;D2;+0:13]#[N;H0;D1;+0:14]>>[C:1]-[#7:2](-[c:3])-[CH2;D2;+0:4]-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10].[C:11]-[C:12]-[CH2;D2;+0:13]-[NH2;D1;+0:14].[OH-;D0:5] | 79 | [{"value": 79.0, "product": "NCC[C@@H](C)N1CCC(CC1)N(C1=CC=CC=C1)CC=1C=NC=CC1C", "details": "PERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | To a solution of (R)-N-[1-(2-cyano-1-methyl-ethyl)-piperidin-4-yl]-4-methyl-N-phenyl-nicotinamide (3.85 g, 10.62 mmol) in THF (150 mL) was added a solution of borane-THF in THF (1.0 M, 63.72 mL, 63.7 mmol) and the reaction was refluxed for 16 h. The reaction was cooled and carefully quenched with 6N HCl (150 mL) and he... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Tertiary amide | Primary amine.Methanol | null | null | c1ccncc1.c1ccccc1.C1CC[NH]CC1 | Other | C1CCOC1 | 65 | null | Cc1ccncc1C(=O)N(c1ccccc1)C1CCN([C@H](C)CC#N)CC1>C1CCOC1>CO.Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCN)CC1.[NH4+].[OH-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f17dc19cfefe40469c44c002235ae5f0 | Cc1cc(C#N)cc(C)c1C(=O)O.Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCN)CC1>>Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(C#N)cc2C)CC1 | C(#N)C1=CC(=C(C(=O)O)C(=C1)C)C.NCC[C@@H](C)N1CCC(CC1)N(C1=CC=CC=C1)CC=1C=NC=CC1C.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.C=1C=CC2=C(C1)N=NN2O>>C(#N)C1=CC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C2=CC=CC=C2)CC=2C=NC=CC2C)C(=C1)C)C | O[C:25](=[O:26])[c:27]1[c:28]([CH3:29])[cH:30][c:31]([C:32]#[N:33])[cH:34][c:35]1[CH3:36].[CH3:1][c:2]1[cH:3][cH:4][n:5][cH:6][c:7]1[CH2:8][N:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[CH:16]1[CH2:17][CH2:18][N:19]([C@H:20]([CH3:21])[CH2:22][CH2:23][NH2:24])[CH2:37][CH2:38]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5][cH:6][c... | Cc1cc(C#N)cc(C)c1C(=O)O.Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCN)CC1 | Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(C#N)cc2C)CC1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCN1CCC(N(Cc2cccnc2)c2ccccc2)CC1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 72 | [{"value": 72.0, "product": "C(#N)C1=CC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C2=CC=CC=C2)CC=2C=NC=CC2C)C(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.9, "product": "C(#N)C1=CC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C2=CC=CC=C2)CC=2C=NC=CC2C)C(=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | 16 | HOUR | [1-((R)-3-Amino-1-methyl-propyl)-piperidin-4-yl]-(4-methyl-pyridin-3-ylmethyl)-phenyl-amine (200.0 mg, 0.57 mmol), EDCI (120.0 mg, 0.62 mmol) and HOBT (84.3 mg, 0.62 mmol) were combined in DMF (25 mL) to give a pale yellow solution. To this solution was added 4-cyano-2,6-dimethyl-benzoic acid (109.3 mg, 0.62 mmol) foll... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HO- | CN(C)C=O | null | 16 | Cc1cc(C#N)cc(C)c1C(=O)O.Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCN)CC1>CN(C)C=O>Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(C#N)cc2C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-16b1df0fd357424aa4c0d37b5488b6f8 | CCO.Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(C#N)cc2C)CC1.[OH-]>>Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(C(=O)O)cc2C)CC1 | C(#N)C1=CC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C2=CC=CC=C2)CC=2C=NC=CC2C)C(=C1)C)C.[OH-].[Na+].CCO>>CC=1C=C(C(=O)O)C=C(C1C(=O)NCC[C@@H](C)N1CCC(CC1)N(C1=CC=CC=C1)CC=1C=NC=CC1C)C | CC[OH:34].N#[C:32][c:31]1[cH:30][c:28]([CH3:29])[c:27]([C:25]([NH:24][CH2:23][CH2:22][C@H:20]([N:19]2[CH2:18][CH2:17][CH:16]([N:9]([CH2:8][c:7]3[c:2]([CH3:1])[cH:3][cH:4][n:5][cH:6]3)[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[CH2:39][CH2:38]2)[CH3:21])=[O:26])[c:36]([CH3:37])[cH:35]1.[OH-:33]>>[CH3:1][c:2]1[cH:3][cH:... | CCO.Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(C#N)cc2C)CC1.[OH-] | Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(C(=O)O)cc2C)CC1 | null | null | null | Acylation | OtherReaction | e41cdaf6ecb9257286a05c8e01433d124042c5939fb4d758964487a1f4637b56 | e38d1b350c527156572f58ef95bb65354ed43ce776b83f166b6fd042d5d9aca9 | O=C(NCCCN1CCC(N(Cc2cccnc2)c2ccccc2)CC1)c1ccccc1 | C-C-[OH;D1;+0:1].N#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[OH-;D0:6]>>[O;H0;D1;+0:6]=[C;H0;D3;+0:2](-[OH;D1;+0:1])-[c:3](:[c:4]):[c:5] | 100 | [{"value": 100.0, "product": "CC=1C=C(C(=O)O)C=C(C1C(=O)NCC[C@@H](C)N1CCC(CC1)N(C1=CC=CC=C1)CC=1C=NC=CC1C)C", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 18 | HOUR | To a solution of 4-cyano-2,6-dimethyl-N-((R)-3-{4-[(4-methyl-pyridin-3-ylmethyl)-phenyl-amino]-piperidin-1-yl}-butyl)-benzamide (0.21 g, 0.41 mmol) in EtOH (10 mL) was added 3N NaOH (5 mL) and the resulting colourless solution was stirred at 100° C. for 18 h. The EtOH was removed in vacuo and the pH adjusted to ˜5 befo... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary alcohol | Carboxylic acid | null | null | c1ccncc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1 | Other | null | 100 | 18 | CCO.Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(C#N)cc2C)CC1.[OH-]>>Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(C(=O)O)cc2C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-48e0b91def02474b9c6d4b1794f25246 | CC(C)N.Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(C(=O)O)cc2C)CC1>>Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(C(=O)NC(C)C)cc2C)CC1 | C(C)(C)N.CC=1C=C(C(=O)O)C=C(C1C(=O)NCC[C@@H](C)N1CCC(CC1)N(C1=CC=CC=C1)CC=1C=NC=CC1C)C.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.C=1C=CC2=C(C1)N=NN2O>>C(C)(C)NC(C1=CC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C2=CC=CC=C2)CC=2C=NC=CC2C)C(=C1)C)C)=O | [NH2:34][CH:35]([CH3:36])[CH3:37].O[C:32]([c:31]1[cH:30][c:28]([CH3:29])[c:27]([C:25]([NH:24][CH2:23][CH2:22][C@H:20]([N:19]2[CH2:18][CH2:17][CH:16]([N:9]([CH2:8][c:7]3[c:2]([CH3:1])[cH:3][cH:4][n:5][cH:6]3)[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[CH2:42][CH2:41]2)[CH3:21])=[O:26])[c:39]([CH3:40])[cH:38]1)=[O:33]>>... | CC(C)N.Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(C(=O)O)cc2C)CC1 | Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(C(=O)NC(C)C)cc2C)CC1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCN1CCC(N(Cc2cccnc2)c2ccccc2)CC1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[NH2;D1;+0:9]>>[C;D1;H3:6]-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 19.7 | [{"value": 19.0, "product": "C(C)(C)NC(C1=CC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C2=CC=CC=C2)CC=2C=NC=CC2C)C(=C1)C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 19.7, "product": "C(C)(C)NC(C1=CC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C2=CC=CC=C2)CC=2C=NC=CC2C)C(=C1)C)C)=O", "details": "CALCULATEDPERCENTYIELD",... | null | null | 16 | HOUR | 3,5-Dimethyl-N-((R)-3-{4-[(4-methyl-pyridin-3-ylmethyl)-phenyl-amino]-piperidin-1-yl}-butyl)-terephthalamic acid (50.0 mg, 0.09 mmol), EDCI (19.9 mg, 0.10 mmol) and HOBT (14.1 mg, 0.10 mmol) were combined in DMF (4 mL) to give a pale yellow solution. To this solution was added isopropylamine (8.9 μL, 0.10 mmol) followe... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1.C1CC[NH]CC1.c1ccccc1 | HO- | CN(C)C=O | null | 16 | CC(C)N.Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(C(=O)O)cc2C)CC1>CN(C)C=O>Cc1ccncc1CN(c1ccccc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(C(=O)NC(C)C)cc2C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-009a55b55ebb41f9a3d31789259d28a7 | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1cc(F)nc(C)c1C(=O)O>>COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(F)nc3C)CC2)cc1 | NCC[C@@H](C)N1CCC(CC1)N(CC=1C=NC=CC1C)C1=CC=C(C=C1)OC.FC1=NC(=C(C(=O)O)C(=C1)C)C.C=1C=CC2=C(C1)N=NN2O.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>>FC1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=C1)C)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH2:8][c:9]2[cH:10][n:11][cH:12][cH:13][c:14]2[CH3:15])[CH:16]2[CH2:17][CH2:18][N:19]([C@H:20]([CH3:21])[CH2:22][CH2:23][NH2:24])[CH2:36][CH2:37]2)[cH:38][cH:39]1.O[C:25](=[O:26])[c:27]1[c:28]([CH3:29])[cH:30][c:31]([F:32])[n:33][c:34]1[CH3:35]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][... | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1cc(F)nc(C)c1C(=O)O | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(F)nc3C)CC2)cc1 | null | null | [Cl-].[Na+].O.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCN1CCC(N(Cc2cccnc2)c2ccccc2)CC1)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8] | 68.1 | [{"value": 67.0, "product": "FC1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.1, "product": "FC1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | null | null | null | null | To a solution of [1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-(4-methoxy-phenyl)-(4-methyl-pyridin-3-ylmethyl)-amine (41 mg, 0.11 mmol) in DMF (0.5 mL) was added 6-fluoro-2,4-dimethyl-nicotinic acid (27 mg, 0.16 mmol), HOBT (20 mg, 0.15 mmol), EDCI (29 mg, 0.15 mmol) and DIPEA (55 μL, 0.32 mmol). After the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HO- | [Cl-].[Na+].O.CN(C)C=O | null | null | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1cc(F)nc(C)c1C(=O)O>[Cl-].[Na+].O.CN(C)C=O>COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(F)nc3C)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6008e08859864474be49f332de1a7652 | CCOc1ccc(N)cc1.C[C@H](CC#N)N1CCC(=O)CC1>>CCOc1ccc(NC2CCN([C@H](C)CC#N)CC2)cc1 | C(C)OC1=CC=C(N)C=C1.O=C1CCN(CC1)[C@@H](CC#N)C.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].C(=O)(O)[O-].[Na+].[OH-].[Na+]>>C(C)OC1=CC=C(C=C1)NC1CCN(CC1)[C@@H](CC#N)C | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:20][cH:21]1.O=[C:9]1[CH2:10][CH2:11][N:12]([C@H:13]([CH3:14])[CH2:15][C:16]#[N:17])[CH2:18][CH2:19]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH:8][CH:9]2[CH2:10][CH2:11][N:12]([C@H:13]([CH3:14])[CH2:15][C:16]#[N:17])[CH2:18][CH2:19]2)[cH:20][cH:21]1 | CCOc1ccc(N)cc1.C[C@H](CC#N)N1CCC(=O)CC1 | CCOc1ccc(NC2CCN([C@H](C)CC#N)CC2)cc1 | null | CC(=O)O | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 42e9e55fb09951ae64da272b20a0fe6708e6155493933c6a5b57bd203fbe3626 | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(NC2CCNCC2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:10] | 90 | [{"value": 90.0, "product": "C(C)OC1=CC=C(C=C1)NC1CCN(CC1)[C@@H](CC#N)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Following General Procedure A, a solution of 4-ethoxyaniline (0.48 g, 3.5 mmol) and (R)-3-(4-oxo-piperidin-1-yl)butyronitrile (0.49 g, 3.0 mmol) in CH2Cl2 (10 mL), was treated with glacial AcOH (3 drops) and NaBH(OAc)3 (0.93 g, 4.4 mmol), stirring for 16 h at room temperature. Saturated aqueous NaHCO3 solution (15 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | Other | CC(=O)O.C(Cl)Cl | null | 16 | CCOc1ccc(N)cc1.C[C@H](CC#N)N1CCC(=O)CC1>CC(=O)O.C(Cl)Cl>CCOc1ccc(NC2CCN([C@H](C)CC#N)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b222b2d037df440cacc60dbb104c5f4c | CCN(C(C)C)C(C)C.CCOc1ccc(NC2CCN([C@H](C)CC#N)CC2)cc1.Cl.O=C(Cl)c1cccnc1>>CCOc1ccc(N(C(=O)c2cccnc2)C2CCN([C@H](C)CC#N)CC2)cc1.ClCc1cccnc1 | C(C)OC1=CC=C(C=C1)NC1CCN(CC1)[C@@H](CC#N)C.Cl.C(C1=CN=CC=C1)(=O)Cl.CCN(C(C)C)C(C)C>>C(#N)C[C@@H](C)N1CCC(CC1)N(C(C1=CN=CC=C1)=O)C1=CC=C(C=C1)OCC.C(C1=CN=CC=C1)Cl | C[CH:31]([CH3:33])[N:36]([CH:35](C)[CH3:34])[CH2:37][CH3:32].[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH:8][CH:17]2[CH2:18][CH2:19][N:20]([C@H:21]([CH3:22])[CH2:23][C:24]#[N:25])[CH2:26][CH2:27]2)[cH:28][cH:29]1.[ClH:30].Cl[C:9](=[O:10])[c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6... | CCN(C(C)C)C(C)C.CCOc1ccc(NC2CCN([C@H](C)CC#N)CC2)cc1.Cl.O=C(Cl)c1cccnc1 | CCOc1ccc(N(C(=O)c2cccnc2)C2CCN([C@H](C)CC#N)CC2)cc1.ClCc1cccnc1 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | e0330530606d6a784d3a70e2975704cfc9607cf1c87b227e245980f6b85a023d | ee406d30f86b8705704e3298f32e9c2647763f41aea1b8edb9be2a097ae8bcfd | O=C(c1cccnc1)N(c1ccccc1)C1CCNCC1.c1ccncc1 | C-[CH;D3;+0:1](-[CH3;D1;+0:2])-[N;H0;D3;+0:3](-[CH2;D2;+0:4]-[CH3;D1;+0:5])-[CH;D3;+0:6](-C)-[CH3;D1;+0:7].Cl-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c:10](:[c:11]):[c:12]:[#7;a:13]:[c:14].[C:15]-[C:16](-[NH;D2;+0:17]-[c:18](:[c:19]):[c:20])-[C:21].[ClH;D0;+0:22]>>[C:15]-[C:16](-[N;H0;D3;+0:17](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c:1... | 88 | [{"value": 88.0, "product": "C(C1=CN=CC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 16 | HOUR | A solution of the above nitrile (0.18 g, 0.63 mmol) and nicotinoyl chloride hydrochloride (0.45 g, 2.5 mmol) in THF (6 mL) was then treated with DIPEA (0.55 mL, 3.2 mmol) and stirred at 80° C. for 16 h. The reaction was cooled to room temperature, concentrated under reduced pressure, diluted with CH2Cl2 (10 mL) and was... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine.Tertiary amine | Primary halide.Tertiary amide | null | c1ccncc1 | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HCl | C1CCOC1 | 80 | 16 | CCN(C(C)C)C(C)C.CCOc1ccc(NC2CCN([C@H](C)CC#N)CC2)cc1.Cl.O=C(Cl)c1cccnc1>C1CCOC1>CCOc1ccc(N(C(=O)c2cccnc2)C2CCN([C@H](C)CC#N)CC2)cc1.ClCc1cccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4d0e8fd9f7064dabb9e665dcb627e0c5 | COCCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1cc(Cl)nc(C)c1C(=O)O>>COCCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(Cl)nc3C)CC2)cc1 | NCC[C@@H](C)N1CCC(CC1)N(CC=1C=NC=CC1C)C1=CC=C(C=C1)OCCOC.CC1=C(C(=O)O)C(=CC(=N1)Cl)C.CCN(C(C)C)C(C)C.C=1C=CC2=C(C1)N=NN2O.CCN=C=NCCCN(C)C>>ClC1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OCCOC)C(=C1)C)C | [CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([N:10]([CH2:11][c:12]2[cH:13][n:14][cH:15][cH:16][c:17]2[CH3:18])[CH:19]2[CH2:20][CH2:21][N:22]([C@H:23]([CH3:24])[CH2:25][CH2:26][NH2:27])[CH2:39][CH2:40]2)[cH:41][cH:42]1.O[C:28](=[O:29])[c:30]1[c:31]([CH3:32])[cH:33][c:34]([Cl:35])[n:36][c:37]1[CH3:38]>>[CH3:1][... | COCCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1cc(Cl)nc(C)c1C(=O)O | COCCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(Cl)nc3C)CC2)cc1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCN1CCC(N(Cc2cccnc2)c2ccccc2)CC1)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8] | 23 | [{"value": 23.0, "product": "ClC1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OCCOC)C(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 22.8, "product": "ClC1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OCCOC)C(=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | 8 | HOUR | Following General Procedure C: To a solution of [1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-[4-(2-methoxy-ethoxy)-phenyl]-(4-methyl-pyridin-3-ylmethyl)-amine (130 mg, 0.31 mmol) and 2,4-dimethyl-6-chloronicotinic acid (68 mg, 0.31 mmol) in DMF (4 mL) was added DIPEA (0.8 mL), HOBT (75 mg, 0.56 mmol) and EDCI (89 m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HO- | CN(C)C=O | null | 8 | COCCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1cc(Cl)nc(C)c1C(=O)O>CN(C)C=O>COCCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(Cl)nc3C)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cadf53cc475544a8893ff05390b03c61 | CCOc1ccc(NC2CCN([C@H](C)CC#N)CC2)cc1.Cc1ccncc1C(=O)O>>CCOc1ccc(N(C(=O)c2cnccc2C)C2CCN([C@H](C)CC#N)CC2)cc1 | Cl.CC1=CC=NC=C1C(=O)O.C(C)OC1=CC=C(C=C1)NC1CCN(CC1)[C@@H](CC#N)C.CCN(CC)CC.C(C(=O)Cl)(=O)Cl>>C(#N)C[C@@H](C)N1CCC(CC1)N(C(C1=CN=CC=C1C)=O)C1=CC=C(C=C1)OCC | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([NH:8][CH:18]2[CH2:19][CH2:20][N:21]([C@H:22]([CH3:23])[CH2:24][C:25]#[N:26])[CH2:27][CH2:28]2)[cH:29][cH:30]1.O[C:9](=[O:10])[c:11]1[cH:12][n:13][cH:14][cH:15][c:16]1[CH3:17]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([N:8]([C:9](=[O:10])[c:11]2[cH:12][n:13][cH:14][cH:15][c:... | CCOc1ccc(NC2CCN([C@H](C)CC#N)CC2)cc1.Cc1ccncc1C(=O)O | CCOc1ccc(N(C(=O)c2cnccc2C)C2CCN([C@H](C)CC#N)CC2)cc1 | null | CN(C)C=O | C(Cl)Cl.C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cccnc1)N(c1ccccc1)C1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C:8]-[C:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:14]>>[C:8]-[C:9](-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7])-[c:11](:[c:12]):[c:13])-[C:14] | null | [] | null | null | 2 | HOUR | 4-Methyl-nicotinic acid hydrochloride (0.83 g, 4.8 mmol) was suspended in CH2Cl2 (25 mL) with DMF (6 drops). Oxalyl chloride (2.5 mL, 28.8 mmol) was added and the mixture stirred at room temperature for 2 h. The homogenous solution was then concentrated and dried in vacuo. To the solid was added THF (12.5 mL) and a sol... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1 | HO- | CN(C)C=O.C(Cl)Cl.C1CCOC1 | null | 2 | CCOc1ccc(NC2CCN([C@H](C)CC#N)CC2)cc1.Cc1ccncc1C(=O)O>CN(C)C=O.C(Cl)Cl.C1CCOC1>CCOc1ccc(N(C(=O)c2cnccc2C)C2CCN([C@H](C)CC#N)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4d29fa598da24304a5781972f6286d78 | Cc1ccncc1C(=O)N(c1ccc(C(F)(F)F)nc1)C1CCN([C@H](C)CC#N)CC1>>Cc1ccncc1CN(c1ccc(C(F)(F)F)nc1)C1CCN([C@H](C)CCN)CC1 | C(#N)C[C@@H](C)N1CCC(CC1)N(C(C1=CN=CC=C1C)=O)C=1C=NC(=CC1)C(F)(F)F.B.C1CCOC1>>NCC[C@@H](C)N1CCC(CC1)N(C=1C=NC(=CC1)C(F)(F)F)CC=1C=NC=CC1C | O=[C:8]([c:7]1[c:2]([CH3:1])[cH:3][cH:4][n:5][cH:6]1)[N:9]([c:10]1[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[n:18][cH:19]1)[CH:20]1[CH2:21][CH2:22][N:23]([C@H:24]([CH3:25])[CH2:26][C:27]#[N:28])[CH2:29][CH2:30]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5][cH:6][c:7]1[CH2:8][N:9]([c:10]1[cH:11][cH:12][c:13]([C:14]([F:15])([... | Cc1ccncc1C(=O)N(c1ccc(C(F)(F)F)nc1)C1CCN([C@H](C)CC#N)CC1 | Cc1ccncc1CN(c1ccc(C(F)(F)F)nc1)C1CCN([C@H](C)CCN)CC1 | null | null | C1CCOC1 | Reduction | OtherReaction | 145ac75eaac85beafa8bb4a24bfe019f61f7a12bff255f993b524d9d1bef1b2e | 50a36b824468b74e90e51d9cad0696fc1ccde4d0c59bcf6da5360a81d82b2e71 | c1cncc(CN(c2cccnc2)C2CCNCC2)c1 | O=[C;H0;D3;+0:1](-[#7:2](-[C:3])-[c:4]:[c:5]:[#7;a:6])-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11].[C:12]-[C:13]-[C;H0;D2;+0:14]#[N;H0;D1;+0:15]>>[#7;a:6]:[c:5]:[c:4]-[#7:2](-[C:3])-[CH2;D2;+0:1]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11].[C:12]-[C:13]-[CH2;D2;+0:14]-[NH2;D1;+0:15] | 58.5 | [{"value": 58.0, "product": "NCC[C@@H](C)N1CCC(CC1)N(C=1C=NC(=CC1)C(F)(F)F)CC=1C=NC=CC1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.5, "product": "NCC[C@@H](C)N1CCC(CC1)N(C=1C=NC(=CC1)C(F)(F)F)CC=1C=NC=CC1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | To a solution of (R)-N-[1-(2-cyano-1-methyl-ethyl)-piperidin-4-yl]-4-methyl-N-(6-trifluoromethyl-pyridin-3-yl)-nicotinamide (0.62 g, 1.44 mmol) in THF (25 mL) was added a solution of borane-THF in THF (1.0 M, 8.62 mL, 8.62 mmol) and the reaction was refluxed for 16 h. The reaction was cooled and carefully quenched with... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Tertiary amide | Primary amine | null | null | c1ccncc1.c1ccncc1.C1CC[NH]CC1 | Other | C1CCOC1 | 65 | null | Cc1ccncc1C(=O)N(c1ccc(C(F)(F)F)nc1)C1CCN([C@H](C)CC#N)CC1>C1CCOC1>Cc1ccncc1CN(c1ccc(C(F)(F)F)nc1)C1CCN([C@H](C)CCN)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bf83bf337f5742bfbdeac286f7db7407 | Cc1cc(Cl)nc(C)c1C(=O)O.Cc1ccncc1CN(c1ccc(C(F)(F)F)nc1)C1CCN([C@H](C)CCN)CC1>>Cc1ccncc1CN(c1ccc(C(F)(F)F)nc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(Cl)nc2C)CC1 | Cl.ClC1=NC(=C(C(=O)O)C(=C1)C)C.NCC[C@@H](C)N1CCC(CC1)N(C=1C=NC(=CC1)C(F)(F)F)CC=1C=NC=CC1C.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.C=1C=CC2=C(C1)N=NN2O>>ClC1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C=2C=NC(=CC2)C(F)(F)F)CC=2C=NC=CC2C)C(=C1)C)C | O[C:29](=[O:30])[c:31]1[c:32]([CH3:33])[cH:34][c:35]([Cl:36])[n:37][c:38]1[CH3:39].[CH3:1][c:2]1[cH:3][cH:4][n:5][cH:6][c:7]1[CH2:8][N:9]([c:10]1[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[n:18][cH:19]1)[CH:20]1[CH2:21][CH2:22][N:23]([C@H:24]([CH3:25])[CH2:26][CH2:27][NH2:28])[CH2:40][CH2:41]1>>[CH3:1][c:2]1[cH:... | Cc1cc(Cl)nc(C)c1C(=O)O.Cc1ccncc1CN(c1ccc(C(F)(F)F)nc1)C1CCN([C@H](C)CCN)CC1 | Cc1ccncc1CN(c1ccc(C(F)(F)F)nc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(Cl)nc2C)CC1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCN1CCC(N(Cc2cccnc2)c2cccnc2)CC1)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;D1;H3:6]):[#7;a:7]:[c:8] | 61 | [{"value": 60.0, "product": "ClC1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C=2C=NC(=CC2)C(F)(F)F)CC=2C=NC=CC2C)C(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.0, "product": "ClC1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C=2C=NC(=CC2)C(F)(F)F)CC=2C=NC=CC2C)C(=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "... | null | null | 16 | HOUR | [1-((R)-3-Amino-1-methyl-propyl)-piperidin-4-yl]-(4-methyl-pyridin-3-ylmethyl)-(6-trifluoromethyl-pyridin-3-yl)-amine (72.9 mg, 0.17 mmol), EDCI (36.4 mg, 0.19 mmol) and HOBT (25.7 mg, 0.19 mmol) were combined in DMF (5 mL) to give a pale yellow solution. To this solution was added 6-chloro-2,4-dimethyl-nicotinic acid ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HO- | CN(C)C=O | null | 16 | Cc1cc(Cl)nc(C)c1C(=O)O.Cc1ccncc1CN(c1ccc(C(F)(F)F)nc1)C1CCN([C@H](C)CCN)CC1>CN(C)C=O>Cc1ccncc1CN(c1ccc(C(F)(F)F)nc1)C1CCN([C@H](C)CCNC(=O)c2c(C)cc(Cl)nc2C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a764643ff0e4c8383b34a0d4d0450ea | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1ccnc(Cl)c1C(=O)O>>COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)ccnc3Cl)CC2)cc1 | ClC1=C(C(=O)O)C(=CC=N1)C.NCC[C@@H](C)N1CCC(CC1)N(CC=1C=NC=CC1C)C1=CC=C(C=C1)OC.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.C=1C=CC2=C(C1)N=NN2O>>ClC1=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=CC=N1)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH2:8][c:9]2[cH:10][n:11][cH:12][cH:13][c:14]2[CH3:15])[CH:16]2[CH2:17][CH2:18][N:19]([C@H:20]([CH3:21])[CH2:22][CH2:23][NH2:24])[CH2:35][CH2:36]2)[cH:37][cH:38]1.O[C:25](=[O:26])[c:27]1[c:28]([CH3:29])[cH:30][cH:31][n:32][c:33]1[Cl:34]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:... | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1ccnc(Cl)c1C(=O)O | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)ccnc3Cl)CC2)cc1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCN1CCC(N(Cc2cccnc2)c2ccccc2)CC1)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8] | 57.8 | [{"value": 57.0, "product": "ClC1=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=CC=N1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.8, "product": "ClC1=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=CC=N1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | 25 | CELSIUS | 16 | HOUR | (R)-[1-(3-Amino-1-methyl-propyl)-piperidin-4-yl]-(4-methoxy-phenyl)-(4-methyl-pyridin-3-ylmethyl)-amine (0.077 g, 0.20 mmol), EDCI (0.043 g, 0.22 mmol) and HOBT (0.030 g, 0.22 mmol) were combined in DMF (5 mL) to give a pale yellow solution. To this solution was added 2-chloro-4-methyl-nicotinic acid (0.038 g, 0.22 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HO- | CN(C)C=O | 25 | 16 | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1ccnc(Cl)c1C(=O)O>CN(C)C=O>COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)ccnc3Cl)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b8ae91da14864fe0bf8de2cacaeb0d4d | C[C@H](CC#N)N1CCC(=O)CC1.Nc1ccc(OC(F)F)cc1>>C[C@H](CC#N)N1CCC(Nc2ccc(OC(F)F)cc2)CC1 | FC(OC1=CC=C(N)C=C1)F.O=C1CCN(CC1)[C@@H](CC#N)C.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].C(=O)(O)[O-].[Na+].[OH-].[Na+]>>FC(OC1=CC=C(C=C1)NC1CCN(CC1)[C@@H](CC#N)C)F | O=[C:9]1[CH2:8][CH2:7][N:6]([C@H:2]([CH3:1])[CH2:3][C:4]#[N:5])[CH2:22][CH2:21]1.[NH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH:16]([F:17])[F:18])[cH:19][cH:20]1>>[CH3:1][C@H:2]([CH2:3][C:4]#[N:5])[N:6]1[CH2:7][CH2:8][CH:9]([NH:10][c:11]2[cH:12][cH:13][c:14]([O:15][CH:16]([F:17])[F:18])[cH:19][cH:20]2)[CH2:21][CH2:22]1 | C[C@H](CC#N)N1CCC(=O)CC1.Nc1ccc(OC(F)F)cc1 | C[C@H](CC#N)N1CCC(Nc2ccc(OC(F)F)cc2)CC1 | null | CC(=O)O | C(Cl)Cl | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 42e9e55fb09951ae64da272b20a0fe6708e6155493933c6a5b57bd203fbe3626 | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc(NC2CCNCC2)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[NH;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:10] | 76 | [{"value": 76.0, "product": "FC(OC1=CC=C(C=C1)NC1CCN(CC1)[C@@H](CC#N)C)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.8, "product": "FC(OC1=CC=C(C=C1)NC1CCN(CC1)[C@@H](CC#N)C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Following General Procedure A, a solution of 4-difluoromethoxyaniline (0.50 g, 3.1 mmol) and (R)-3-(4-oxo-piperidin-1-yl)-butyronitrile (0.44 g, 2.6 mmol) in CH2Cl2 (10 mL), was treated with glacial AcOH (3 drops) and NaBH(OAc)3 (0.83 g, 3.9 mmol), stirring for 16 h at room temperature. Saturated aqueous NaHCO3 solutio... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | Other | CC(=O)O.C(Cl)Cl | null | 16 | C[C@H](CC#N)N1CCC(=O)CC1.Nc1ccc(OC(F)F)cc1>CC(=O)O.C(Cl)Cl>C[C@H](CC#N)N1CCC(Nc2ccc(OC(F)F)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-509ba96307904656baf9865e99f729ea | C[C@H](CC#N)N1CCC(Nc2ccc(OC(F)F)cc2)CC1.O=C(Cl)c1cccnc1>>C[C@H](CC#N)N1CCC(N(C(=O)c2cccnc2)c2ccc(OC(F)F)cc2)CC1 | FC(OC1=CC=C(C=C1)NC1CCN(CC1)[C@@H](CC#N)C)F.Cl.C(C1=CN=CC=C1)(=O)Cl.CCN(C(C)C)C(C)C>>C(#N)C[C@@H](C)N1CCC(CC1)N(C(C1=CN=CC=C1)=O)C1=CC=C(C=C1)OC(F)F | [CH3:1][C@H:2]([CH2:3][C:4]#[N:5])[N:6]1[CH2:7][CH2:8][CH:9]([NH:10][c:19]2[cH:20][cH:21][c:22]([O:23][CH:24]([F:25])[F:26])[cH:27][cH:28]2)[CH2:29][CH2:30]1.Cl[C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1>>[CH3:1][C@H:2]([CH2:3][C:4]#[N:5])[N:6]1[CH2:7][CH2:8][CH:9]([N:10]([C:11](=[O:12])[c:13]2[cH:14][cH:... | C[C@H](CC#N)N1CCC(Nc2ccc(OC(F)F)cc2)CC1.O=C(Cl)c1cccnc1 | C[C@H](CC#N)N1CCC(N(C(=O)c2cccnc2)c2ccc(OC(F)F)cc2)CC1 | null | null | C1CCOC1 | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1cccnc1)N(c1ccccc1)C1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C:8]-[C:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13])-[C:14]>>[C:8]-[C:9](-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7])-[c:11](:[c:12]):[c:13])-[C:14] | 39 | [{"value": 39.0, "product": "C(#N)C[C@@H](C)N1CCC(CC1)N(C(C1=CN=CC=C1)=O)C1=CC=C(C=C1)OC(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.6, "product": "C(#N)C[C@@H](C)N1CCC(CC1)N(C(C1=CN=CC=C1)=O)C1=CC=C(C=C1)OC(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 16 | HOUR | A solution of the above nitrile (0.20 g, 0.65 mmol) and nicotinoyl chloride hydrochloride (0.46 g, 2.6 mmol) in THF (6 mL) was then treated with DIPEA (0.56 mL, 3.2 mmol) and stirred at 80° C. for 16 h. The reaction was cooled to room temperature, concentrated under reduced pressure, diluted with CH2Cl2 (10 mL) and was... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | C1CC[NH]CC1.c1ccncc1.c1ccccc1 | HCl | C1CCOC1 | 80 | 16 | C[C@H](CC#N)N1CCC(Nc2ccc(OC(F)F)cc2)CC1.O=C(Cl)c1cccnc1>C1CCOC1>C[C@H](CC#N)N1CCC(N(C(=O)c2cccnc2)c2ccc(OC(F)F)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9596365c0fe4c79911357cfa34a672d | COCCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1ccnc(Cl)c1C(=O)O>>COCCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)ccnc3Cl)CC2)cc1 | ClC1=C(C(=O)O)C(=CC=N1)C.NCC[C@@H](C)N1CCC(CC1)N(CC=1C=NC=CC1C)C1=CC=C(C=C1)OCCOC.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.C=1C=CC2=C(C1)N=NN2O>>ClC1=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OCCOC)C(=CC=N1)C | [CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([N:10]([CH2:11][c:12]2[cH:13][n:14][cH:15][cH:16][c:17]2[CH3:18])[CH:19]2[CH2:20][CH2:21][N:22]([C@H:23]([CH3:24])[CH2:25][CH2:26][NH2:27])[CH2:38][CH2:39]2)[cH:40][cH:41]1.O[C:28](=[O:29])[c:30]1[c:31]([CH3:32])[cH:33][cH:34][n:35][c:36]1[Cl:37]>>[CH3:1][O:2][CH2:... | COCCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1ccnc(Cl)c1C(=O)O | COCCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)ccnc3Cl)CC2)cc1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCN1CCC(N(Cc2cccnc2)c2ccccc2)CC1)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8] | 78.1 | [{"value": 76.0, "product": "ClC1=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OCCOC)C(=CC=N1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.1, "product": "ClC1=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OCCOC)C(=CC=N1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | 25 | CELSIUS | 16 | HOUR | (R)-[1-(3-Amino-1-methyl-propyl)-piperidin-4-yl]-[4-(2-methoxy-ethoxy)-phenyl]-(4-methyl-pyridin-3-ylmethyl)-amine (0.065 g, 0.15 mmol), EDCI (0.033 g, 0.17 mmol) and HOBT (0.023 g, 0.17 mmol) were combined in DMF (5 mL) to give a pale yellow solution. To this solution was added 2-chloro-4-methyl-nicotinic acid (0.029 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HO- | CN(C)C=O | 25 | 16 | COCCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1ccnc(Cl)c1C(=O)O>CN(C)C=O>COCCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)ccnc3Cl)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-66b8ab9f484d48448421cd75e67fabc9 | Cc1c(Br)cnc(N)c1Br>>Cc1ccnc(N)c1Br | BrC=1C(=NC=C(C1C)Br)N.[Li]CCCC>>BrC=1C(=NC=CC1C)N | Br[c:3]1[c:2]([CH3:1])[c:8]([Br:9])[c:6]([NH2:7])[n:5][cH:4]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([NH2:7])[c:8]1[Br:9] | Cc1c(Br)cnc(N)c1Br | Cc1ccnc(N)c1Br | null | null | C1CCOC1 | Functional Group Interconversion | Aromatic dehalogenation | ea85ec2fde5700c76b45764563e70d433b50e38e1af4209f646f155266c8ec96 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1-[C;D1;H3:7]>>[C;D1;H3:7]-[c:6]1:[c:5]:[c:4]:[#7;a:3]:[c:2]:[cH;D2;+0:1]:1 | 71 | [{"value": 71.0, "product": "BrC=1C(=NC=CC1C)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.7, "product": "BrC=1C(=NC=CC1C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | To a solution of 3,5-dibromo-4-methyl-pyridin-2-ylamine (3.38 g, 12.7 mmol) in THF (60 mL) cooled to −78° C. was added n-BuLi (1.9M in pentane) (13.4 mL, 25.4 mmol) to give an orange solution. The solution was stirred at −78° C. for 1 h and then quenched with water (10 mL). The pH of the mixture was adjusted to ˜12 wit... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1 | c1ccncc1 | c1ccncc1 | Br- | C1CCOC1 | -78 | 1 | Cc1c(Br)cnc(N)c1Br>C1CCOC1>Cc1ccnc(N)c1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f5e070cde61946ea91f96e687bae81a4 | BrBr.Cc1ccnc(N)c1Br>>Cc1ccnc(Br)c1Br | BrBr.BrC=1C(=NC=CC1C)N.N(=O)[O-].[Na+]>>BrC1=NC=CC(=C1Br)C | Br[Br:7].N[c:6]1[n:5][cH:4][cH:3][c:2]([CH3:1])[c:8]1[Br:9]>>[CH3:1][c:2]1[cH:3][cH:4][n:5][c:6]([Br:7])[c:8]1[Br:9] | BrBr.Cc1ccnc(N)c1Br | Cc1ccnc(Br)c1Br | null | null | O.Br | Functional Group Interconversion | OtherReaction | c34356dee62682a5768cf6d77cd41509a1ca5fa7825c2ccee4407118d8ca7dbf | 9c224743a26d9e1c3135e4817dd611aec414d8ea156f02200a3aef865be78b01 | c1ccncc1 | Br-[Br;H0;D1;+0:1].N-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5](-[Br;D1;H0:6]):[c:7]>>[Br;D1;H0:6]-[c:5](:[c:7]):[c;H0;D3;+0:2](-[Br;H0;D1;+0:1]):[#7;a:3]:[c:4] | 47 | [{"value": 47.0, "product": "BrC1=NC=CC(=C1Br)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.5, "product": "BrC1=NC=CC(=C1Br)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | null | null | Bromine (0.35 mL, 6.8 mmol) was added dropwise to a solution of 3-bromo-4-methyl-pyridin-2-ylamine (0.44 g, 2.4 mmol) in 48% HBr (3 mL) at −10° C. to give an orange slurry. After 5 minutes NaNO2 (0.47 g, 6.8 mmol), dissolved in water (1.5 mL), was added dropwise over 5 minutes. The dark brown mixture was slowly warmed ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | O.Br | 10 | null | BrBr.Cc1ccnc(N)c1Br>O.Br>Cc1ccnc(Br)c1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-64312fea85674ba9a2d7a2e8a7d0e318 | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1ccnc(Br)c1C(=O)O>>COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)ccnc3Br)CC2)cc1 | BrC1=C(C(=O)O)C(=CC=N1)C.NCC[C@@H](C)N1CCC(CC1)N(CC=1C=NC=CC1C)C1=CC=C(C=C1)OC.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.C=1C=CC2=C(C1)N=NN2O>>BrC1=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=CC=N1)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH2:8][c:9]2[cH:10][n:11][cH:12][cH:13][c:14]2[CH3:15])[CH:16]2[CH2:17][CH2:18][N:19]([C@H:20]([CH3:21])[CH2:22][CH2:23][NH2:24])[CH2:35][CH2:36]2)[cH:37][cH:38]1.O[C:25](=[O:26])[c:27]1[c:28]([CH3:29])[cH:30][cH:31][n:32][c:33]1[Br:34]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:... | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1ccnc(Br)c1C(=O)O | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)ccnc3Br)CC2)cc1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCN1CCC(N(Cc2cccnc2)c2ccccc2)CC1)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Br;D1;H0:6]):[#7;a:7]:[c:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[Br;D1;H0:6]-[c:5](:[#7;a:7]:[c:8]):[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C:10]-[C:9]):[c:4] | 38.3 | [{"value": 38.0, "product": "BrC1=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=CC=N1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.3, "product": "BrC1=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OC)C(=CC=N1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | 25 | CELSIUS | 16 | HOUR | (R)-[1-(3-Amino-1-methyl-propyl)-piperidin-4-yl]-(4-methoxy-phenyl)-(4-methyl-pyridin-3-ylmethyl)-amine (0.070 g, 0.18 mmol), EDCI (0.039 g, 0.20 mmol) and HOBT (0.027 g, 0.20 mmol) were combined in DMF (5 mL) to give a pale yellow solution. To this solution was added 2-bromo-4-methyl-nicotinic acid (0.043 g, 0.20 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HO- | CN(C)C=O | 25 | 16 | COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1ccnc(Br)c1C(=O)O>CN(C)C=O>COc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)ccnc3Br)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-873476fe926049c0be1279e11060cac2 | CCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1ccnc(Cl)c1C(=O)O>>CCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)ccnc3Cl)CC2)cc1 | ClC1=C(C(=O)O)C(=CC=N1)C.NCC[C@@H](C)N1CCC(CC1)N(CC=1C=NC=CC1C)C1=CC=C(C=C1)OCC.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.C=1C=CC2=C(C1)N=NN2O>>ClC1=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OCC)C(=CC=N1)C | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([N:8]([CH2:9][c:10]2[cH:11][n:12][cH:13][cH:14][c:15]2[CH3:16])[CH:17]2[CH2:18][CH2:19][N:20]([C@H:21]([CH3:22])[CH2:23][CH2:24][NH2:25])[CH2:36][CH2:37]2)[cH:38][cH:39]1.O[C:26](=[O:27])[c:28]1[c:29]([CH3:30])[cH:31][cH:32][n:33][c:34]1[Cl:35]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5]... | CCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1ccnc(Cl)c1C(=O)O | CCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)ccnc3Cl)CC2)cc1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCN1CCC(N(Cc2cccnc2)c2ccccc2)CC1)c1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[Cl;D1;H0:6]):[#7;a:7]:[c:8] | 61 | [{"value": 61.0, "product": "ClC1=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OCC)C(=CC=N1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.6, "product": "ClC1=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(CC=2C=NC=CC2C)C2=CC=C(C=C2)OCC)C(=CC=N1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | 16 | HOUR | [1-((R)-3-Amino-1-methyl-propyl)-piperidin-4-yl]-(4-ethoxy-phenyl)-(4-methyl-pyridin-3-ylmethyl)-amine (58.0 mg, 0.15 mmol), EDCI (30.9 mg, 0.16 mmol) and HOBT (21.8 mg, 0.16 mmol) were combined in DMF (5 mL) to give a pale yellow solution. To this solution was added 2-chloro-4-methyl-nicotinic acid (27.5 mg, 0.16 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HO- | CN(C)C=O | null | 16 | CCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCN)CC2)cc1.Cc1ccnc(Cl)c1C(=O)O>CN(C)C=O>CCOc1ccc(N(Cc2cnccc2C)C2CCN([C@H](C)CCNC(=O)c3c(C)ccnc3Cl)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-923f14f00a2b451ba7dd9e5e227f76e2 | COc1ccc(NC2CCN([C@H](C)CC#N)CC2)cc1>>COc1ccc(NC2CCN([C@H](C)CCN)CC2)cc1 | COC1=CC=C(C=C1)NC1CCN(CC1)[C@@H](CC#N)C>>NCC[C@@H](C)N1CCC(CC1)NC1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH:8]2[CH2:9][CH2:10][N:11]([C@H:12]([CH3:13])[CH2:14][C:15]#[N:16])[CH2:17][CH2:18]2)[cH:19][cH:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH:8]2[CH2:9][CH2:10][N:11]([C@H:12]([CH3:13])[CH2:14][CH2:15][NH2:16])[CH2:17][CH2:18]2)[cH:19][cH:20]1 | COc1ccc(NC2CCN([C@H](C)CC#N)CC2)cc1 | COc1ccc(NC2CCN([C@H](C)CCN)CC2)cc1 | null | [Ni] | CO.N | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(NC2CCNCC2)cc1 | [C:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | null | [] | null | null | 8 | HOUR | (R)-3-[4-(4-Methoxy-phenylamino)-piperidin-1-yl]-butyronitrile (0.53 g, 1.94 mmol) was dissolved in NH3 saturated MeOH (15 mL), treated with Raney nickel (excess), and placed under 45 psi H2 on a Parr shaker for 8 h. In a standard work-up the mixture was diluted with MeOH and filtered through celite. The cake was washe... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.C1CC[NH]CC1 | null | [Ni].CO.N | null | 8 | COc1ccc(NC2CCN([C@H](C)CC#N)CC2)cc1>[Ni].CO.N>COc1ccc(NC2CCN([C@H](C)CCN)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-164f1aed3a24455c921e368e084b7b1e | COc1ccc(NC2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1.N#Cc1cccc(CBr)n1>>COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1 | C(C)(C)(C)OC(NCC[C@@H](C)N1CCC(CC1)NC1=CC=C(C=C1)OC)=O.BrCC1=CC=CC(=N1)C#N.CCN(C(C)C)C(C)C>>C(C)(C)(C)OC(NCC[C@@H](C)N1CCC(CC1)N(C1=CC=C(C=C1)OC)CC1=NC(=CC=C1)C#N)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH:17]2[CH2:18][CH2:19][N:20]([C@H:21]([CH3:22])[CH2:23][CH2:24][NH:25][C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[CH2:33][CH2:34]2)[cH:35][cH:36]1.Br[CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([C:14]#[N:15])[n:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH2:8][... | COc1ccc(NC2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1.N#Cc1cccc(CBr)n1 | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1 | null | null | CC#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(N(Cc2ccccn2)C2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7](-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:12]>>[C:6]-[C:7](-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5])-[c:9](:[c:10]):[c:11])-[C:12] | 78 | [{"value": 78.0, "product": "C(C)(C)(C)OC(NCC[C@@H](C)N1CCC(CC1)N(C1=CC=C(C=C1)OC)CC1=NC(=CC=C1)C#N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.9, "product": "C(C)(C)(C)OC(NCC[C@@H](C)N1CCC(CC1)N(C1=CC=C(C=C1)OC)CC1=NC(=CC=C1)C#N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure E, (R)-{3-[4-(4-methoxy-phenylamino)-piperidin-1-yl]-butyl}-carbamic acid tert-butyl ester (0.681 g, 1.81 mmol), 6-bromomethyl-pyridine-2-carbonitrile (0.535 g, 2.71 mmol) and DIPEA (630 μL, 3.62 mmol) in CH3CN (20 mL) at 55° C. for 16 h gave the crude product as a pale brown oil. Purification b... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1 | HBr | CC#N | null | null | COc1ccc(NC2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1.N#Cc1cccc(CBr)n1>CC#N>COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e9f423d680642f49868daadd69064aa | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1.Cc1cc(C#N)cc(C)c1C(=O)O>>COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C#N)cc3C)CC2)cc1 | C(#N)C1=CC(=C(C(=O)O)C(=C1)C)C.CCN=C=NCCCN(C)C.C(C)(C)(C)OC(NCC[C@@H](C)N1CCC(CC1)N(C1=CC=C(C=C1)OC)CC1=NC(=CC=C1)C#N)=O.CCN(C(C)C)C(C)C.C=1C=CC2=C(C1)N=NN2O>>C(#N)C1=CC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C2=CC=C(C=C2)OC)CC2=NC(=CC=C2)C#N)C(=C1)C)C | CC(C)(C)O[C:26]([NH:25][CH2:24][CH2:23][C@H:21]([N:20]1[CH2:19][CH2:18][CH:17]([N:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:41][cH:40]2)[CH2:8][c:9]2[cH:10][cH:11][cH:12][c:13]([C:14]#[N:15])[n:16]2)[CH2:39][CH2:38]1)[CH3:22])=[O:27].O=C(O)[c:28]1[c:29]([CH3:30])[cH:31][c:32]([C:33]#[N:34])[cH:35][c:36]1[CH3:37]>>[CH... | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1.Cc1cc(C#N)cc(C)c1C(=O)O | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C#N)cc3C)CC2)cc1 | null | null | CN(C)C=O.C(Cl)Cl.C(=O)(C(F)(F)F)O | C-C Coupling | OtherReaction | f6cbb9addc61c47609dc5a88ea9f6b164426bf8e6967e66955dc9fb763a84567 | 58bf2849600aa08f4eb2f5f9a337b189d08e0e342e283e5c019ad8925a722909 | O=C(NCCCN1CCC(N(Cc2ccccn2)c2ccccc2)CC1)c1ccccc1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4].O-C(=O)-[c;H0;D3;+0:5](:[c:6](-[C;D1;H3:7]):[c:8]):[c:9](-[C;D1;H3:10]):[c:11]>>[C:4]-[#7:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:5](:[c:6](-[C;D1;H3:7]):[c:8]):[c:9](-[C;D1;H3:10]):[c:11] | 55.8 | [{"value": 55.0, "product": "C(#N)C1=CC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C2=CC=C(C=C2)OC)CC2=NC(=CC=C2)C#N)C(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.8, "product": "C(#N)C1=CC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C2=CC=C(C=C2)OC)CC2=NC(=CC=C2)C#N)C(=C1)C)C", "details": "CALCULATEDPERCENTYIELD",... | null | null | 1 | HOUR | (R)-(3-{4-[(6-Cyano-pyridin-2-ylmethyl)-(4-methoxy-phenyl)-amino]-piperidin-1-yl}-butyl)-carbamic acid tert-butyl ester (0.070 g, 0.14 mmol) was dissolved in a 3:1 mixture of CH2Cl2 and TFA and the mixture was stirred at room temperature for 1 h. The solvent was removed in vacuo and the resulting brown oil dried in vac... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Boc | Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccccc1 | HO- | CN(C)C=O.C(Cl)Cl.C(=O)(C(F)(F)F)O | null | 1 | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1.Cc1cc(C#N)cc(C)c1C(=O)O>CN(C)C=O.C(Cl)Cl.C(=O)(C(F)(F)F)O>COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C#N)cc3C)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2f1e8ce4e9b34e55bd6d302d6990b5ae | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1.Cc1cc(F)nc(C)c1C(=O)O>>COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(F)nc3C)CC2)cc1 | Cl.FC1=NC(=C(C(=O)O)C(=C1)C)C.CCN=C=NCCCN(C)C.C(C)(C)(C)OC(NCC[C@@H](C)N1CCC(CC1)N(C1=CC=C(C=C1)OC)CC1=NC(=CC=C1)C#N)=O.CCN(C(C)C)C(C)C.C=1C=CC2=C(C1)N=NN2O>>C(#N)C1=CC=CC(=N1)CN(C1CCN(CC1)[C@@H](CCNC(C1=C(N=C(C=C1C)F)C)=O)C)C1=CC=C(C=C1)OC | CC(C)(C)OC(=O)[NH:25][CH2:24][CH2:23][C@H:21]([N:20]1[CH2:19][CH2:18][CH:17]([N:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:40][cH:39]2)[CH2:8][c:9]2[cH:10][cH:11][cH:12][c:13]([C:14]#[N:15])[n:16]2)[CH2:38][CH2:37]1)[CH3:22].O[C:26](=[O:27])[c:28]1[c:29]([CH3:30])[cH:31][c:32]([F:33])[n:34][c:35]1[CH3:36]>>[CH3:1][O:2... | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1.Cc1cc(F)nc(C)c1C(=O)O | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(F)nc3C)CC2)cc1 | null | null | CN(C)C=O.C(Cl)Cl.C(=O)(C(F)(F)F)O | Acylation | OtherReaction | 510680c124a6407ad270065ce067b02da7b27d9b855c374df163b757a8749f7f | 7457c724cd0cfe2d26ffa0aef6c4027e2d3dc4704bac959e83de51cafcce5bb3 | O=C(NCCCN1CCC(N(Cc2ccccn2)c2ccccc2)CC1)c1cccnc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8](-[C;D1;H3:9]):[#7;a:10]:[c:11]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8](-[C;D1;H3:9]):[#7;a:10]:[c:11] | 76.1 | [{"value": 75.0, "product": "C(#N)C1=CC=CC(=N1)CN(C1CCN(CC1)[C@@H](CCNC(C1=C(N=C(C=C1C)F)C)=O)C)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.1, "product": "C(#N)C1=CC=CC(=N1)CN(C1CCN(CC1)[C@@H](CCNC(C1=C(N=C(C=C1C)F)C)=O)C)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_des... | null | null | 1 | HOUR | (R)-(3-{4-[(6-Cyano-pyridin-2-ylmethyl)-(4-methoxy-phenyl)-amino]-piperidin-1-yl}-butyl)-carbamic acid tert-butyl ester (0.070 g, 0.14 mmol) was dissolved in a 3:1 mixture of CH2Cl2 and TFA and the mixture was stirred at room temperature for 1 h. The solvent was removed in vacuo and the resulting brown oil dried in vac... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Boc | Secondary amide | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HO- | CN(C)C=O.C(Cl)Cl.C(=O)(C(F)(F)F)O | null | 1 | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1.Cc1cc(F)nc(C)c1C(=O)O>CN(C)C=O.C(Cl)Cl.C(=O)(C(F)(F)F)O>COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(F)nc3C)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2cc05f7aaf1049909b4586b2e824f3de | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1.Cc1cc(C#N)nc(C)c1C(=O)O>>COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C#N)nc3C)CC2)cc1 | Cl.C(#N)C1=NC(=C(C(=O)O)C(=C1)C)C.CCN=C=NCCCN(C)C.C(C)(C)(C)OC(NCC[C@@H](C)N1CCC(CC1)N(C1=CC=C(C=C1)OC)CC1=NC(=CC=C1)C#N)=O.CCN(C(C)C)C(C)C.C=1C=CC2=C(C1)N=NN2O>>C(#N)C1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C2=CC=C(C=C2)OC)CC2=NC(=CC=C2)C#N)C(=C1)C)C | CC(C)(C)OC(=O)[NH:25][CH2:24][CH2:23][C@H:21]([N:20]1[CH2:19][CH2:18][CH:17]([N:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:41][cH:40]2)[CH2:8][c:9]2[cH:10][cH:11][cH:12][c:13]([C:14]#[N:15])[n:16]2)[CH2:39][CH2:38]1)[CH3:22].O[C:26](=[O:27])[c:28]1[c:29]([CH3:30])[cH:31][c:32]([C:33]#[N:34])[n:35][c:36]1[CH3:37]>>[CH3... | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1.Cc1cc(C#N)nc(C)c1C(=O)O | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C#N)nc3C)CC2)cc1 | null | null | CN(C)C=O.C(Cl)Cl.C(=O)(C(F)(F)F)O | Acylation | OtherReaction | 510680c124a6407ad270065ce067b02da7b27d9b855c374df163b757a8749f7f | 7457c724cd0cfe2d26ffa0aef6c4027e2d3dc4704bac959e83de51cafcce5bb3 | O=C(NCCCN1CCC(N(Cc2ccccn2)c2ccccc2)CC1)c1cccnc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8](-[C;D1;H3:9]):[#7;a:10]:[c:11]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8](-[C;D1;H3:9]):[#7;a:10]:[c:11] | 53.1 | [{"value": 52.0, "product": "C(#N)C1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C2=CC=C(C=C2)OC)CC2=NC(=CC=C2)C#N)C(=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.1, "product": "C(#N)C1=NC(=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C2=CC=C(C=C2)OC)CC2=NC(=CC=C2)C#N)C(=C1)C)C", "details": "CALCULATEDPERCENTYIELD",... | null | null | 1 | HOUR | (R)-(3-{4-[(6-Cyano-pyridin-2-ylmethyl)-(4-methoxy-phenyl)-amino]-piperidin-1-yl}-butyl)-carbamic acid tert-butyl ester (0.070 g, 0.14 mmol) was dissolved in a 3:1 mixture of CH2Cl2 and TFA and the mixture was stirred at room temperature for 1 h. The solvent was removed in vacuo and the resulting brown oil dried in vac... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Boc | Secondary amide | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HO- | CN(C)C=O.C(Cl)Cl.C(=O)(C(F)(F)F)O | null | 1 | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1.Cc1cc(C#N)nc(C)c1C(=O)O>CN(C)C=O.C(Cl)Cl.C(=O)(C(F)(F)F)O>COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)c3c(C)cc(C#N)nc3C)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e725ff071635471b80f28a376be5b3e6 | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1.Cc1ccnc(Cl)c1C(=O)O>>COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)c3c(C)ccnc3Cl)CC2)cc1 | ClC1=C(C(=O)O)C(=CC=N1)C.CCN=C=NCCCN(C)C.C(C)(C)(C)OC(NCC[C@@H](C)N1CCC(CC1)N(C1=CC=C(C=C1)OC)CC1=NC(=CC=C1)C#N)=O.CCN(C(C)C)C(C)C.C=1C=CC2=C(C1)N=NN2O>>ClC1=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C2=CC=C(C=C2)OC)CC2=NC(=CC=C2)C#N)C(=CC=N1)C | CC(C)(C)OC(=O)[NH:25][CH2:24][CH2:23][C@H:21]([N:20]1[CH2:19][CH2:18][CH:17]([N:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:39][cH:38]2)[CH2:8][c:9]2[cH:10][cH:11][cH:12][c:13]([C:14]#[N:15])[n:16]2)[CH2:37][CH2:36]1)[CH3:22].O[C:26](=[O:27])[c:28]1[c:29]([CH3:30])[cH:31][cH:32][n:33][c:34]1[Cl:35]>>[CH3:1][O:2][c:3]1[... | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1.Cc1ccnc(Cl)c1C(=O)O | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)c3c(C)ccnc3Cl)CC2)cc1 | null | null | CN(C)C=O.C(Cl)Cl.C(=O)(C(F)(F)F)O | Acylation | OtherReaction | 510680c124a6407ad270065ce067b02da7b27d9b855c374df163b757a8749f7f | 7457c724cd0cfe2d26ffa0aef6c4027e2d3dc4704bac959e83de51cafcce5bb3 | O=C(NCCCN1CCC(N(Cc2ccccn2)c2ccccc2)CC1)c1cccnc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8](-[Cl;D1;H0:9]):[#7;a:10]:[c:11]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8](-[Cl;D1;H0:9]):[#7;a:10]:[c:11] | 35.3 | [{"value": 35.0, "product": "ClC1=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C2=CC=C(C=C2)OC)CC2=NC(=CC=C2)C#N)C(=CC=N1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.3, "product": "ClC1=C(C(=O)NCC[C@@H](C)N2CCC(CC2)N(C2=CC=C(C=C2)OC)CC2=NC(=CC=C2)C#N)C(=CC=N1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired... | null | null | 1 | HOUR | (R)-(3-{4-[(6-Cyano-pyridin-2-ylmethyl)-(4-methoxy-phenyl)-amino]-piperidin-1-yl}-butyl)-carbamic acid tert-butyl ester (0.070 g, 0.14 mmol) was dissolved in a 3:1 mixture of CH2Cl2 and TFA and the mixture was stirred at room temperature for 1 h. The solvent was removed in vacuo and the resulting brown oil dried in vac... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Boc | Secondary amide | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HO- | CN(C)C=O.C(Cl)Cl.C(=O)(C(F)(F)F)O | null | 1 | COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)OC(C)(C)C)CC2)cc1.Cc1ccnc(Cl)c1C(=O)O>CN(C)C=O.C(Cl)Cl.C(=O)(C(F)(F)F)O>COc1ccc(N(Cc2cccc(C#N)n2)C2CCN([C@H](C)CCNC(=O)c3c(C)ccnc3Cl)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-585dcb13e0bd4a6797ca4f3ed0712af5 | CC(=O)OO.Fc1cc(Cl)ccc1Br>>Oc1c(Cl)ccc(Br)c1F | C(C)(=O)OO.BrC1=C(C=C(C=C1)Cl)F.C(C)(C)[N-]C(C)C.[Li+].B(OC)(OC)OC>>BrC=1C(=C(C(=CC1)Cl)O)F | CC(=O)O[OH:1].[cH:2]1[c:3]([Cl:4])[cH:5][cH:6][c:7]([Br:8])[c:9]1[F:10]>>[OH:1][c:2]1[c:3]([Cl:4])[cH:5][cH:6][c:7]([Br:8])[c:9]1[F:10] | CC(=O)OO.Fc1cc(Cl)ccc1Br | Oc1c(Cl)ccc(Br)c1F | null | null | O1CCCC1.O | Heteroatom Alkylation and Arylation | OtherReaction | ae2c40671d5fdb818f0b6d803c1d8cceca080b6105aceeca1808a097ec52d441 | a2fdf414569b219d462bc05c91ebf31e5426b96645f5c78cb091f50cc92fc345 | c1ccccc1 | C-C(=O)-O-[OH;D1;+0:1].[Cl;D1;H0:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](-[F;D1;H0:7]):[c:8]>>[Cl;D1;H0:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[OH;D1;+0:1]):[c:6](-[F;D1;H0:7]):[c:8] | 63 | [{"value": 63.0, "product": "BrC=1C(=C(C(=CC1)Cl)O)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | null | null | A solution of 1-bromo-4-chloro-2-fluorobenzene (20.4 g, 0.100 mol) in tetrahydrofuran (THF; 50 mL) was slowly added to lithium diisopropyl amide (LDA; 0.125 mol) in THF (600 mL) at −50° C. After addition the solution was warmed to −20° C. and then cooled to −50° C. and a solution of trimethyl borate (13.5 g, 0.130 mol)... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | O1CCCC1.O | -20 | null | CC(=O)OO.Fc1cc(Cl)ccc1Br>O1CCCC1.O>Oc1c(Cl)ccc(Br)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b402ece11d846a0aa5858661deb5eb4 | CI.Oc1c(Cl)ccc(Br)c1F>>COc1c(Cl)ccc(Br)c1F | BrC=1C(=C(C(=CC1)Cl)O)F.CI.C([O-])([O-])=O.[K+].[K+]>>BrC1=C(C(=C(C=C1)Cl)OC)F | I[CH3:1].[OH:2][c:3]1[c:4]([Cl:5])[cH:6][cH:7][c:8]([Br:9])[c:10]1[F:11]>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][cH:7][c:8]([Br:9])[c:10]1[F:11] | CI.Oc1c(Cl)ccc(Br)c1F | COc1c(Cl)ccc(Br)c1F | null | null | C(C)#N.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccccc1 | I-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 96.9 | [{"value": 96.9, "product": "BrC1=C(C(=C(C=C1)Cl)OC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A heterogeneous mixture of 3-bromo-6-chloro-2-fluorophenol (14.4 g, 0.064 mol), methyl iodide (13.5 g, 0.096 mol) and potassium carbonate (8.8 g, 0.064 mol) in acetonitrile (100 mL) was heated under reflux for 2 hours. The mixture was cooled, diluted with water (100 mL) and extracted with ethyl ether (2×150 mL). The co... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1 | HI | C(C)#N.O | null | null | CI.Oc1c(Cl)ccc(Br)c1F>C(C)#N.O>COc1c(Cl)ccc(Br)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9e31a094b5ad4c52a5d3d502c4b2d626 | COc1cc(N)c(F)cc1Cl.[Br-]>>COc1cc(Br)c(F)cc1Cl | ClC1=CC(=C(N)C=C1OC)F.N(=O)[O-].[Na+].C(Cl)Cl.[Br-]>>BrC1=C(C=C(C(=C1)OC)Cl)F | N[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:10]([Cl:11])[cH:9][c:7]1[F:8].[Br-:6]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[c:7]([F:8])[cH:9][c:10]1[Cl:11] | COc1cc(N)c(F)cc1Cl.[Br-] | COc1cc(Br)c(F)cc1Cl | null | null | O.Br.C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | f4fea6a3c7b007f3829d29d893f3499a4094808c0f3b2211f4c3483919a690d8 | 9c224743a26d9e1c3135e4817dd611aec414d8ea156f02200a3aef865be78b01 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[Br-;H0;D0:7]>>[Br;H0;D1;+0:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6] | 49 | [{"value": 49.0, "product": "BrC1=C(C=C(C(=C1)OC)Cl)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 4-chloro-2-fluoro-5-methoxyaniline (25.0 g, 0.143 mol) in 10% HBr (250 mL) was cooled to 0° C. and a solution of sodium nitrite (15.0 g, 0.218 mol) in water (20 mL) was slowly added. Methylene chloride (50 mL) and curpric bromide (30.0 g, 0.244 mol) were added slowly and then the mixture was warmed to amb... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O.Br.C(C)(=O)OCC | null | 1 | COc1cc(N)c(F)cc1Cl.[Br-]>O.Br.C(C)(=O)OCC>COc1cc(Br)c(F)cc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1aaeb1a5cbf84234ad79bcf0802c033b | O=C([O-])C(F)(F)Cl.Oc1c(Cl)ccc(Br)c1F>>Fc1c(Br)ccc(Cl)c1OC(F)F | Cl.BrC=1C(=C(C(=CC1)Cl)O)F.ClC(C(=O)[O-])(F)F.[Na+].C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>>BrC1=C(C(=C(C=C1)Cl)OC(F)F)F | O=C([O-])[C:11](Cl)([F:12])[F:13].[F:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][c:7]([Cl:8])[c:9]1[OH:10]>>[F:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][c:7]([Cl:8])[c:9]1[O:10][CH:11]([F:12])[F:13] | O=C([O-])C(F)(F)Cl.Oc1c(Cl)ccc(Br)c1F | Fc1c(Br)ccc(Cl)c1OC(F)F | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 76f211f5353542c9b838eb8e1b527f9863b90e0b018b98c3cf34f50f16bd6596 | 5bf13e9b56816027718c6488fc8075a60a5c356ea2671f45c1f3f8f299767493 | c1ccccc1 | Cl-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;D1;H0:3])-C(=O)-[O-].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[F;D1;H0:2]-[CH;D3;+0:1](-[F;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 100 | CELSIUS | 8 | HOUR | To a solution of 3-bromo-6-chloro-2-fluorophenol (1.00 g, 4.44 mmol) and sodium chlorodifluoroacetate in dimethylformamide (DMF; 9 mL) was added potassium carbonate (1.22 g, 5.32 mmol) and water (1.77 mL) and the resulting mixture heated to 100° C. for 4 hours. The solution was cooled to ambient temperature and concent... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Aromatic alcohol | Secondary halide.Secondary halide.Ether | null | null | c1ccccc1 | Other | O.CN(C=O)C | 100 | 8 | O=C([O-])C(F)(F)Cl.Oc1c(Cl)ccc(Br)c1F>O.CN(C=O)C>Fc1c(Br)ccc(Cl)c1OC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c5668ed9c68646b79a8599eb7a65ab66 | CS(=O)(=O)OCC(F)F.Oc1c(Cl)ccc(Br)c1F>>Fc1c(Br)ccc(Cl)c1OCC(F)F | BrC=1C(=C(C(=CC1)Cl)O)F.[H-].[Na+].FC(COS(=O)(=O)C)F>>BrC1=C(C(=C(C=C1)Cl)OCC(F)F)F | CS(=O)(=O)O[CH2:11][CH:12]([F:13])[F:14].[F:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][c:7]([Cl:8])[c:9]1[OH:10]>>[F:1][c:2]1[c:3]([Br:4])[cH:5][cH:6][c:7]([Cl:8])[c:9]1[O:10][CH2:11][CH:12]([F:13])[F:14] | CS(=O)(=O)OCC(F)F.Oc1c(Cl)ccc(Br)c1F | Fc1c(Br)ccc(Cl)c1OCC(F)F | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 57201f1afbda3b7775282ca8e3c59a4fb8e542f888bbdbfa994f08238598f88e | b300ae9ac00448343b04f8595ac10c40ddc175401f75ad1a9cb423839305bb59 | c1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[F;D1;H0:3])-[F;D1;H0:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[F;D1;H0:3]-[C:2](-[F;D1;H0:4])-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8] | 45.6 | [{"value": 45.6, "product": "BrC1=C(C(=C(C=C1)Cl)OCC(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 1 | HOUR | A solution of 3-bromo-6-chloro-2-fluorophenol (15.4 g, 0.068 mol) in DMF (25 mL) was slowly added to a suspension of sodium hydride (60% dispersion in mineral oil) (4.0 g, 0.10 mol) in DMF (100 mL) and the mixture was stirred 1 hour. A solution of methanesulfonic acid 2,2 difluoroethyl ester (17.5 g, 0.109 mol) in DMF ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic alcohol | Ether | null | null | c1ccccc1 | MsOH.HO- | O.CN(C)C=O | 70 | 1 | CS(=O)(=O)OCC(F)F.Oc1c(Cl)ccc(Br)c1F>O.CN(C)C=O>Fc1c(Br)ccc(Cl)c1OCC(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-955dd2f4770745cb8dcda679fed99e91 | CSSC.Fc1cc(Cl)ccc1Br>>CSc1c(Cl)ccc(Br)c1F | BrC1=C(C=C(C=C1)Cl)F.[Li+].CC(C)[N-]C(C)C.CSSC>>BrC1=C(C(=C(C=C1)Cl)SC)F | CS[S:2][CH3:1].[cH:3]1[c:4]([Cl:5])[cH:6][cH:7][c:8]([Br:9])[c:10]1[F:11]>>[CH3:1][S:2][c:3]1[c:4]([Cl:5])[cH:6][cH:7][c:8]([Br:9])[c:10]1[F:11] | CSSC.Fc1cc(Cl)ccc1Br | CSc1c(Cl)ccc(Br)c1F | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | d3282bc7b18a5238324cec9d9661038d24b458acad1e5f5aaf30ae469238a3ba | 19099c5abc7af7f1b3d32ffaaaa6b84236f3e8c2bf9cb204008fe61bb9aa47e2 | c1ccccc1 | C-S-[S;H0;D2;+0:1]-[C;D1;H3:2].[Cl;D1;H0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7](-[F;D1;H0:8]):[c:9]>>[C;D1;H3:2]-[S;H0;D2;+0:1]-[c;H0;D3;+0:6](:[c:7](-[F;D1;H0:8]):[c:9]):[c:4](-[Cl;D1;H0:3]):[c:5] | 94 | [{"value": 94.0, "product": "BrC1=C(C(=C(C=C1)Cl)SC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | null | null | A solution of 1-bromo-4-chloro-2-fluorobenzene (20.4 g, 0.100 mol) in THF (50 mL) was slowly added to LDA (0.125 mol) in THF (600 mL) at −50° C. After addition, the solution was warmed to −20° C. and then cooled to −50° C. and a solution of dimethyldisulfide (18.8 g, 0.20 mol) in THF (50 mL) was slowly added and the mi... | 10.6084/m9.figshare.5104873.v1 | null | Disulfide | Monosulfide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C1CCOC1 | -20 | null | CSSC.Fc1cc(Cl)ccc1Br>C1CCOC1>CSc1c(Cl)ccc(Br)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9e560e11d2cb4d4284c5573b886e0e13 | CN(C)C=O.Fc1cc(Cl)ccc1Br>>O=Cc1c(Cl)ccc(Br)c1F | BrC1=C(C=C(C=C1)Cl)F.[Li+].CC(C)[N-]C(C)C.CN(C)C=O>>BrC=1C(=C(C=O)C(=CC1)Cl)F | CN(C)[CH:2]=[O:1].[cH:3]1[c:4]([Cl:5])[cH:6][cH:7][c:8]([Br:9])[c:10]1[F:11]>>[O:1]=[CH:2][c:3]1[c:4]([Cl:5])[cH:6][cH:7][c:8]([Br:9])[c:10]1[F:11] | CN(C)C=O.Fc1cc(Cl)ccc1Br | O=Cc1c(Cl)ccc(Br)c1F | null | null | C1CCOC1 | C-C Coupling | OtherReaction | aae5f0134f66d7b9e3ae1bdd9b3a75c7cb29a8908ff53e1c4658205cbcae8547 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccccc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[Cl;D1;H0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7](-[F;D1;H0:8]):[c:9]>>[Cl;D1;H0:3]-[c:4](:[c:5]):[c;H0;D3;+0:6](-[CH;D2;+0:1]=[O;D1;H0:2]):[c:7](-[F;D1;H0:8]):[c:9] | 169 | [{"value": 169.0, "product": "BrC=1C(=C(C=O)C(=CC1)Cl)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | null | null | A solution of 1-bromo-4-chloro-2-fluorobenzene (20.4 g, 0.100 mol) in THF (50 mL) was slowly added to LDA (0.125 mol) in THF (600 mL) at −50° C. After addition the solution was warmed to −20° C. and then cooled to −50° C. and a solution of DMF (14.6 g, 0.20 mol) in THF (50 mL) was slowly added and the reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C1CCOC1 | -20 | null | CN(C)C=O.Fc1cc(Cl)ccc1Br>C1CCOC1>O=Cc1c(Cl)ccc(Br)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dba4a3aa291242509a556925e6a204b4 | COc1c(C(F)F)ccc([N+](=O)[O-])c1Cl>>COc1c(C(F)F)ccc(N)c1Cl | ClC1=C(C=CC(=C1OC)C(F)F)[N+](=O)[O-]>>ClC1=C(N)C=CC(=C1OC)C(F)F | O=[N+:11]([O-])[c:10]1[cH:9][cH:8][c:4]([CH:5]([F:6])[F:7])[c:3]([O:2][CH3:1])[c:12]1[Cl:13]>>[CH3:1][O:2][c:3]1[c:4]([CH:5]([F:6])[F:7])[cH:8][cH:9][c:10]([NH2:11])[c:12]1[Cl:13] | COc1c(C(F)F)ccc([N+](=O)[O-])c1Cl | COc1c(C(F)F)ccc(N)c1Cl | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A solution of crude 2-chloro-4-difluoromethyl-3-methoxy-1-nitro-benzene in ethanol (50 mL) containing 5% palladium on charcoal (250 mg) was hydrogenated (50 psi) for 5 hours. The solution was filtered and concentrated to give 2-chloro-4-difluoromethyl-3-methoxyaniline (1.3 g, 48 mmol): LC/MS (m/z=207).
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)O | null | null | COc1c(C(F)F)ccc([N+](=O)[O-])c1Cl>[Pd].C(C)O>COc1c(C(F)F)ccc(N)c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f99afb92009b46ea86278f95b19f5328 | BrCCBr.COc1cc(NC(=O)C(C)(C)C)ccc1Cl>>COc1c(Cl)ccc(NC(=O)C(C)(C)C)c1Br | C(CBr)Br.C(C(C)(C)C)(=O)NC1=CC(=C(C=C1)Cl)OC.C(CCC)[Li]>>C(C(C)(C)C)(=O)NC1=C(C(=C(C=C1)Cl)OC)Br | BrCC[Br:17].[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16]1>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[C:12]([CH3:13])([CH3:14])[CH3:15])[c:16]1[Br:17] | BrCCBr.COc1cc(NC(=O)C(C)(C)C)ccc1Cl | COc1c(Cl)ccc(NC(=O)C(C)(C)C)c1Br | null | null | O1CCCC1 | Functional Group Interconversion | Bromination | 1bffa9e6a88fc427854b4c2a23217c0f7bd4696a238658efec7eb43cf40affbc | a8fd90d9727001deb7b4d3f63c2c94d8100018754aab15c0aa879096d979fed2 | c1ccccc1 | Br-C-C-[Br;H0;D1;+0:1].[#8:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](-[#7:7]-[C:8]=[O;D1;H0:9]):[c:10]>>[#8:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[Br;H0;D1;+0:1]):[c:6](-[#7:7]-[C:8]=[O;D1;H0:9]):[c:10] | 5.7 | [{"value": 5.7, "product": "C(C(C)(C)C)(=O)NC1=C(C(=C(C=C1)Cl)OC)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | To solution of N-pivaloyl-4-chloro-3-methoxyaniline (5.0 g, 21 mmol) in tetrahydrofuran (60 mL) at −60° C. was added n-butyl lithium (2.5M, 44 mmol). The solution was allowed to warm to 0° C. and stir for 3 hours. Ethylene dibromide (9.9 g, 53 mmol) was added and the solution stirred for 18 hours before being quenched ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | O1CCCC1 | 0 | 3 | BrCCBr.COc1cc(NC(=O)C(C)(C)C)ccc1Cl>O1CCCC1>COc1c(Cl)ccc(NC(=O)C(C)(C)C)c1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96567a27189e4f24a82283a924f1943f | COc1c(Cl)ccc(NC(=O)C(C)(C)C)c1Br.[I-]>>COc1c(Cl)ccc(I)c1Br | [I-].[Na+].C(C(C)(C)C)(=O)NC1=C(C(=C(C=C1)Cl)OC)Br.Cl.[Na].N(=O)[O-].[Na+]>>BrC1=C(C=CC(=C1OC)Cl)I | CC(C)(C)C(=O)N[c:8]1[cH:7][cH:6][c:4]([Cl:5])[c:3]([O:2][CH3:1])[c:10]1[Br:11].[I-:9]>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][cH:7][c:8]([I:9])[c:10]1[Br:11] | COc1c(Cl)ccc(NC(=O)C(C)(C)C)c1Br.[I-] | COc1c(Cl)ccc(I)c1Br | null | null | O1CCOCC1.O.C(Cl)Cl | Functional Group Interconversion | OtherReaction | 6fba08e28e8d005c3adccdac1e1479cbb249317f8fceb7a44e963e642ee0d6a1 | 10d5e9f7ea4e0a6d7c64f3eede8b2722c836d0e851a0ab7fb8f5aa5d2bdff633 | c1ccccc1 | C-C(-C)(-C)-C(=O)-N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[Br;D1;H0:5]):[c:6].[I-;H0;D0:7]>>[Br;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[I;H0;D1;+0:7]):[c:2]:[c:3] | 50 | [{"value": 50.0, "product": "BrC1=C(C=CC(=C1OC)Cl)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A solution of N-pivaloyl-2-bromo-4-chloro-3-methoxyaniline (3.7 g, 1.2 mmol) in dioxane (35 mL) was treated with concentrated hydrochloric acid (35 mL) and the solution heated under reflux for 2 hours. After the solution was cooled the pH was adjusted to 10 by addition of sodium hyrdroxide (50% solution) and extracted ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | O1CCOCC1.O.C(Cl)Cl | null | 0.333333 | COc1c(Cl)ccc(NC(=O)C(C)(C)C)c1Br.[I-]>O1CCOCC1.O.C(Cl)Cl>COc1c(Cl)ccc(I)c1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fcd268e8de5b42bc95b56204352314a9 | COc1c(C)ccc([N+](=O)[O-])c1Cl.O=S(=O)(O)O>>COc1c(C=O)ccc([N+](=O)[O-])c1Cl | ClC=1C(=C(C=CC1[N+](=O)[O-])C)OC.OS(=O)(=O)O>>ClC=1C(=C(C=O)C=CC1[N+](=O)[O-])OC | [CH3:1][O:2][c:3]1[c:4]([CH3:5])[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]1[Cl:14].O=S(=O)(O)[OH:6]>>[CH3:1][O:2][c:3]1[c:4]([CH:5]=[O:6])[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]1[Cl:14] | COc1c(C)ccc([N+](=O)[O-])c1Cl.O=S(=O)(O)O | COc1c(C=O)ccc([N+](=O)[O-])c1Cl | null | [O-2].[O-2].[O-2].[Cr+6] | C(C)(=O)O.C(C)(=O)OC(C)=O | Heteroatom Alkylation and Arylation | OtherReaction | d1efc7b17943090a212233fca54cb5e95d90b7fe4abb2ecc06d4334375905be3 | be117abed4a0a0378ea43d3a5c1ccf903b86823ade7e92fcb09d68743e45d19a | c1ccccc1 | O-S(=O)(=O)-[OH;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | 2.5 | CELSIUS | 30 | MINUTE | A solution of 3-chloro-2-methoxy-4-nitrotoluene (1.0 g, 5.0 mmol) in acetic acid (10 mL) and acetic anhydride (10 mL) was cooled to 5° C. and treated with 1 mL conc. H2SO4. Chromium trioxide (1.4 g, 14 mmol) was added in portions over 10 minutes while the reaction temperature was maintained at 0-5° C. After 30 minutes ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | null | null | c1ccccc1 | HO- | [O-2].[O-2].[O-2].[Cr+6].C(C)(=O)O.C(C)(=O)OC(C)=O | 2.5 | 0.5 | COc1c(C)ccc([N+](=O)[O-])c1Cl.O=S(=O)(O)O>[O-2].[O-2].[O-2].[Cr+6].C(C)(=O)O.C(C)(=O)OC(C)=O>COc1c(C=O)ccc([N+](=O)[O-])c1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fcbc04e978ae47ab8eafe9bfe2015273 | O=Cc1c(Cl)ccc(Br)c1F>>OCc1c(Cl)ccc(Br)c1F | BrC=1C(=C(C=O)C(=CC1)Cl)F.[BH4-].[Na+]>>BrC=1C(=C(C(=CC1)Cl)CO)F | [O:1]=[CH:2][c:3]1[c:4]([Cl:5])[cH:6][cH:7][c:8]([Br:9])[c:10]1[F:11]>>[OH:1][CH2:2][c:3]1[c:4]([Cl:5])[cH:6][cH:7][c:8]([Br:9])[c:10]1[F:11] | O=Cc1c(Cl)ccc(Br)c1F | OCc1c(Cl)ccc(Br)c1F | null | null | O.C(C)O | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 51.2 | [{"value": 51.2, "product": "BrC=1C(=C(C(=CC1)Cl)CO)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3-bromo-6-chloro-2-fluorobenzaldehyde (20.0 g, 0.084 mol) in ethanol (250 mL) was added sodium borohydride (6.4 g, 0.168 mol) and the reaction mixture was stirred at ambient temperature for 1 hour. The mixture was diluted with water (300 mL) and extracted with ethyl acetate (2×200 mL), dried (sodium su... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1 | null | O.C(C)O | null | 1 | O=Cc1c(Cl)ccc(Br)c1F>O.C(C)O>OCc1c(Cl)ccc(Br)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-453b25c3ec724026ab1fa4c7293ea4d7 | CCN(CC)S(F)(F)F.OCc1c(Cl)ccc(Br)c1F>>FCc1c(Cl)ccc(Br)c1F | C(C)N(CC)S(F)(F)F.BrC=1C(=C(C(=CC1)Cl)CO)F.C([O-])(O)=O.[Na+]>>BrC1=C(C(=C(C=C1)Cl)CF)F | CCN(CC)S(F)(F)[F:1].O[CH2:2][c:3]1[c:4]([Cl:5])[cH:6][cH:7][c:8]([Br:9])[c:10]1[F:11]>>[F:1][CH2:2][c:3]1[c:4]([Cl:5])[cH:6][cH:7][c:8]([Br:9])[c:10]1[F:11] | CCN(CC)S(F)(F)F.OCc1c(Cl)ccc(Br)c1F | FCc1c(Cl)ccc(Br)c1F | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | dbbac462603ac033e664af439abb66b6ed7f62a050ec8784cc63432806b53147 | 01bb6897491017986ad23d0ca606d7f8fde10cee91f632739e86b0f2d029f08a | c1ccccc1 | C-C-N(-C-C)-S(-F)(-F)-[F;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[F;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 55.8 | [{"value": 55.8, "product": "BrC1=C(C(=C(C=C1)Cl)CF)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of diethylamino sulfur trifluoride (7.6 g, 0.047 mol) in methylene chloride (25 mL) was slowly added to (3-bromo-6-chloro-2-fluorophenyl) methanol (10.3 g, 0.043 mol) in methylene chloride (150 mL) at 0° C. The solution was stirred at ambient temperature for 1 hour. A saturated solution of sodium bicarbonate... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Tertiary amine | Primary halide | null | null | c1ccccc1 | HF | C(Cl)Cl | null | 1 | CCN(CC)S(F)(F)F.OCc1c(Cl)ccc(Br)c1F>C(Cl)Cl>FCc1c(Cl)ccc(Br)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3a11670a4488410a9c3499f7a22e5f03 | COCBr.Fc1cc(Cl)ccc1Br>>COCc1c(Cl)ccc(Br)c1F | BrC1=C(C=C(C=C1)Cl)F.[Li+].CC(C)[N-]C(C)C.BrCOC>>BrC1=C(C(=C(C=C1)Cl)COC)F | Br[CH2:3][O:2][CH3:1].[cH:4]1[c:5]([Cl:6])[cH:7][cH:8][c:9]([Br:10])[c:11]1[F:12]>>[CH3:1][O:2][CH2:3][c:4]1[c:5]([Cl:6])[cH:7][cH:8][c:9]([Br:10])[c:11]1[F:12] | COCBr.Fc1cc(Cl)ccc1Br | COCc1c(Cl)ccc(Br)c1F | null | null | C1CCOC1 | C-C Coupling | Friedel-Crafts alkylation with halide | 19e1c9ead146f3ec155f78be3301959bd293e8f94fe62cc7a458225e0ca866ed | 2c1c1647472d7e3cff37f0f3aad955b760f0ad2f8b7aa7e7825b1c0344bab3bb | c1ccccc1 | Br-[CH2;D2;+0:1]-[#8:2]-[C;D1;H3:3].[Cl;D1;H0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8](-[F;D1;H0:9]):[c:10]>>[C;D1;H3:3]-[#8:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:7](:[c:8](-[F;D1;H0:9]):[c:10]):[c:5](-[Cl;D1;H0:4]):[c:6] | 71 | [{"value": 71.0, "product": "BrC1=C(C(=C(C=C1)Cl)COC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | null | null | A solution of 1-bromo-4-chloro-2-fluorobenzene (20.4 g, 0.100 mol) in THF (50 mL) was slowly added to LDA (0.125 mol) in THF (600 mL) at −50° C. After addition the solution was warmed to −20° C. and then cooled to −50° C. a solution of bromomethoxymethane (25 g, 0.200 mol) in THF (25 mL) was slowly added and the reacti... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | C1CCOC1 | -20 | null | COCBr.Fc1cc(Cl)ccc1Br>C1CCOC1>COCc1c(Cl)ccc(Br)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b45b3512a22140ab8e825793113bee86 | CC(C)OB(OC(C)C)OC(C)C.COc1c(Cl)ccc(Br)c1F.OCCCO>>COc1c(Cl)ccc(B2OCCCO2)c1F | BrC1=C(C(=C(C=C1)Cl)OC)F.C(CCO)O.C(C)(=O)Cl.C(CCC)[Li].B(OC(C)C)(OC(C)C)OC(C)C>>ClC1=C(C(=C(C=C1)B1OCCCO1)F)OC | CC(C)O[B:9](OC(C)C)OC(C)C.Br[c:8]1[cH:7][cH:6][c:4]([Cl:5])[c:3]([O:2][CH3:1])[c:15]1[F:16].[OH:10][CH2:11][CH2:12][CH2:13][OH:14]>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][cH:7][c:8]([B:9]2[O:10][CH2:11][CH2:12][CH2:13][O:14]2)[c:15]1[F:16] | CC(C)OB(OC(C)C)OC(C)C.COc1c(Cl)ccc(Br)c1F.OCCCO | COc1c(Cl)ccc(B2OCCCO2)c1F | null | null | O.C(C)OCC.C1CCOC1 | Functional Group Interconversion | OtherReaction | f661ccee5fc1a4c61c11642b615e99eb52369a13f2e1274a3105a0cc2139f68f | d81c0ca864a2ec9c27a080d942532d9fa8930cc1f578c7f476bff4d373972e9f | c1ccc(B2OCCCO2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].C-C(-C)-O-[B;H0;D3;+0:7](-O-C(-C)-C)-O-C(-C)-C.[OH;D1;+0:8]-[C:9]-[C:10]-[C:11]-[OH;D1;+0:12]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[B;H0;D3;+0:7]1-[O;H0;D2;+0:8]-[C:9]-[C:10]-[C:11]-[O;H0;D2;+0:12]-1):[c:2]:[c:3] | 144.2 | [{"value": 144.2, "product": "ClC1=C(C(=C(C=C1)B1OCCCO1)F)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a solution of 1-bromo-4-chloro-2-fluoro-3-methoxybenzene (10.4 g, 0.043 mol) in diethyl ether (150 mL) at −78° C. was slowly added n-butyl lithium (2.5M, 19.0 mL, 0.0475 mol) and the solution was stirred for 30 minutes. A solution of triisopropyl borate (12.0 g, 0.064 ml) in THF (25 mL) was slowly added and the solu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol.Primary alcohol | null | c1ccccc1 | c1ccccc1.[B]1OCCCO1 | c1ccccc1.[B]1OCCCO1 | HBr | O.C(C)OCC.C1CCOC1 | 0 | 0.5 | CC(C)OB(OC(C)C)OC(C)C.COc1c(Cl)ccc(Br)c1F.OCCCO>O.C(C)OCC.C1CCOC1>COc1c(Cl)ccc(B2OCCCO2)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a5cb17765ebb4b48bc8f91b25fd05994 | Oc1cccc(F)c1O>>Fc1cccc2c1OCO2 | C=1(O)C(O)=CC=CC1.BrCBr.O.FC1=C(C(O)=CC=C1)O>>FC1=C2C(=CC=C1)OCO2 | [F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([OH:10])[c:7]1[OH:8]>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[O:8][CH2:9][O:10]2 | Oc1cccc(F)c1O | Fc1cccc2c1OCO2 | null | [Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC | C(Cl)Cl.[OH-].[Na+] | Heteroatom Alkylation and Arylation | OtherReaction | 261b172e2e1399cf91c79807980a9085329a50a99ac6290cdd10f912d087070c | b56a881cca53d645d3ea21c88aa2f444e6fbc0455e71d7569115c4e79d3bc912 | c1ccc2c(c1)OCO2 | [OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6]>>[c:6]:[c:4]1:[c:2](:[c:3])-[O;H0;D2;+0:1]-[C:7]-[O;H0;D2;+0:5]-1 | null | [] | null | null | 2 | HOUR | Aliquot 336 (methyltrioctylammonium chloride, 0.63 g, 1.6 mmol), dibromomethane (40.7 g, 234.2 mmol) and water (31 mL) were placed in a 500 mL 3-necked flask equipped with an addition funnel, condenser and a stir bar. The addition funnel was charged with a solution of 3-fluorocatechol (20.0 g, 160 mmol) in 5M sodium hy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol | Ether.Ether | null | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | Other | [Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.C(Cl)Cl.[OH-].[Na+] | null | 2 | Oc1cccc(F)c1O>[Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.C(Cl)Cl.[OH-].[Na+]>Fc1cccc2c1OCO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e2fd3470e2344a3b83e5e13d3941608 | N#Cc1c(Cl)ccc(Br)c1F.O=S(=O)(O)O>>NC(=O)c1c(Cl)ccc(Br)c1F | S(O)(O)(=O)=O.BrC=1C(=C(C#N)C(=CC1)Cl)F.[OH-].[NH4+]>>BrC=1C(=C(C(=O)N)C(=CC1)Cl)F | [N:1]#[C:2][c:4]1[c:5]([Cl:6])[cH:7][cH:8][c:9]([Br:10])[c:11]1[F:12].O=S(=O)(O)[OH:3]>>[NH2:1][C:2](=[O:3])[c:4]1[c:5]([Cl:6])[cH:7][cH:8][c:9]([Br:10])[c:11]1[F:12] | N#Cc1c(Cl)ccc(Br)c1F.O=S(=O)(O)O | NC(=O)c1c(Cl)ccc(Br)c1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1d1793919e847ed86dcb16487e62464531560dbf4782f9a5875bfe7e0477a3ec | d6f9d146e8ef95e62f1a3ab55a7e3b4ceec8856a5f71b6dccd4ad850f945b658 | c1ccccc1 | O-S(=O)(=O)-[OH;D1;+0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[NH2;D1;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4](:[c:5]):[c:6] | null | [] | 55 | CELSIUS | null | null | Concentrated sulfuric acid (15 mL) was placed in a 100 mL 3-neck flask equipped with an internal thermometer and then heated to 55° C. 3-Bromo-2-fluoro-6-chlorobenzonitrile (11.0 g, 47 mmol) was added portion-wise to the acid with stirring maintaining the temperature above 50° C. The dark solution was heated at 65° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | c1ccccc1 | Other | null | 55 | null | N#Cc1c(Cl)ccc(Br)c1F.O=S(=O)(O)O>>NC(=O)c1c(Cl)ccc(Br)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-528c49f2164343678e241c928b704ab5 | COc1c(C)cc(F)cc1F.II>>COc1c(C)cc(F)c(I)c1F | FC1=C(C(=CC(=C1)F)C)OC.[Li+].CC(C)[N-]C(C)C.II>>FC1=C(C(=C(C(=C1)C)OC)F)I | [CH3:1][O:2][c:3]1[c:4]([CH3:5])[cH:6][c:7]([F:8])[cH:9][c:11]1[F:12].I[I:10]>>[CH3:1][O:2][c:3]1[c:4]([CH3:5])[cH:6][c:7]([F:8])[c:9]([I:10])[c:11]1[F:12] | COc1c(C)cc(F)cc1F.II | COc1c(C)cc(F)c(I)c1F | null | null | C(C)(=O)OCC.C1CCOC1 | Functional Group Interconversion | OtherReaction | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | I-[I;H0;D1;+0:1].[F;D1;H0:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](-[F;D1;H0:7]):[c:8]>>[F;D1;H0:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[I;H0;D1;+0:1]):[c:6](-[F;D1;H0:7]):[c:8] | null | [] | null | null | 45 | MINUTE | A solution of 1,5-difluoro-2-methoxy-3-methylbenzene (0.65 g, 4.1 mmol) in THF (1 mL) was added to LDA (4.3 mmol) in THF (10 mL) at −55° C. and the solution stirred for 45 minutes. Solid iodine (1.15 g, 4.5 mmol) was added and the solution allowed to warm to ambient temperature. The solution was diluted with ethyl acet... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | C(C)(=O)OCC.C1CCOC1 | null | 0.75 | COc1c(C)cc(F)cc1F.II>C(C)(=O)OCC.C1CCOC1>COc1c(C)cc(F)c(I)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef75023a8fa04d738e1b8f3f4b2cb0d7 | COc1c(F)cc(F)cc1Cl.II>>COc1c(Cl)cc(F)c(I)c1F | II.ClC1=C(C(=CC(=C1)F)F)OC.C(CCC)[Li]>>ClC1=C(C(=C(C(=C1)F)I)F)OC | [CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([F:8])[cH:9][c:11]1[F:12].I[I:10]>>[CH3:1][O:2][c:3]1[c:4]([Cl:5])[cH:6][c:7]([F:8])[c:9]([I:10])[c:11]1[F:12] | COc1c(F)cc(F)cc1Cl.II | COc1c(Cl)cc(F)c(I)c1F | null | null | S(=S)(=O)([O-])[O-].[Na+].[Na+].C(C)OCC.C1CCOC1 | Functional Group Interconversion | OtherReaction | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | I-[I;H0;D1;+0:1].[F;D1;H0:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](-[F;D1;H0:7]):[c:8]>>[F;D1;H0:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[I;H0;D1;+0:1]):[c:6](-[F;D1;H0:7]):[c:8] | null | [] | -75 | CELSIUS | 1 | HOUR | To a solution of 1-chloro-3,5-difluoro-2-methoxybenzene (2.0 g, 0.01 mol) in THF at −75° C. was added n-butyl lithium (2.5M in hexanes 6.7 mL) and the resulting solution was stirred at −75° C. for 1 hour. A solution of iodine (5.1 g, 0.02 mol) in THF (10 mL) was added and the reaction mixture was allowed to warm to amb... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | S(=S)(=O)([O-])[O-].[Na+].[Na+].C(C)OCC.C1CCOC1 | -75 | 1 | COc1c(F)cc(F)cc1Cl.II>S(=S)(=O)([O-])[O-].[Na+].[Na+].C(C)OCC.C1CCOC1>COc1c(Cl)cc(F)c(I)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-029465e19df24386aaf7b22cb26ff2d0 | CO.N#Cc1ccc(I)c(F)c1F>>COc1c(C#N)ccc(I)c1F | [H-].[Na+].CO.FC1=C(C#N)C=CC(=C1F)I>>FC=1C(=C(C#N)C=CC1I)OC | [CH3:1][OH:2].F[c:3]1[c:4]([C:5]#[N:6])[cH:7][cH:8][c:9]([I:10])[c:11]1[F:12]>>[CH3:1][O:2][c:3]1[c:4]([C:5]#[N:6])[cH:7][cH:8][c:9]([I:10])[c:11]1[F:12] | CO.N#Cc1ccc(I)c(F)c1F | COc1c(C#N)ccc(I)c1F | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 63a067904226f0ed76bf8a0a76c9d06ffd43386e7bc5fe344f44269368a678a1 | 23dafde907f7a74dc1d4cc65967b00a9b318897fe61a3d3c4a9fddf320485f17 | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[C:6]#[N;D1;H0:7]):[c:8].[C;D1;H3:9]-[OH;D1;+0:10]>>[C;D1;H3:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1](:[c:2](-[F;D1;H0:3]):[c:4]):[c:5](-[C:6]#[N;D1;H0:7]):[c:8] | 94.7 | [{"value": 94.7, "product": "FC=1C(=C(C#N)C=CC1I)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 10 | MINUTE | Sodium hydride (60 mg, 2.5 mmol) was slurried in DMF (15 mL) and treated with dry methanol (120 μl, 96 mg, 3.0 mmol). After stirring for 10 minutes at 25° C., the solution was cooled to −25° C. and treated with 2,3-difluoro-4-iodobenzonitrile (500 mg, 1.9 mmol). After 25 minutes, the mixture was quenched by addition of... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Methanol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | CN(C)C=O | 25 | 0.166667 | CO.N#Cc1ccc(I)c(F)c1F>CN(C)C=O>COc1c(C#N)ccc(I)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a2ad7ceeffe43bcbd3611d485143db7 | Cc1ccc(F)c(N)c1F.O=S(=O)(Cl)Cl>>Cc1c(Cl)cc(F)c(N)c1F | FC1=C(N)C(=CC=C1C)F.S(=O)(=O)(Cl)Cl>>ClC1=C(C(=C(N)C(=C1)F)F)C | [CH3:1][c:2]1[cH:3][cH:5][c:6]([F:7])[c:8]([NH2:9])[c:10]1[F:11].O=S(=O)(Cl)[Cl:4]>>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][c:6]([F:7])[c:8]([NH2:9])[c:10]1[F:11] | Cc1ccc(F)c(N)c1F.O=S(=O)(Cl)Cl | Cc1c(Cl)cc(F)c(N)c1F | null | null | C(C)(=O)O | Functional Group Interconversion | Chlorination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Cl-S(=O)(=O)-[Cl;H0;D1;+0:1].[C;D1;H3:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[C;D1;H3:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[Cl;H0;D1;+0:1]):[c:6]:[c:7] | 65.7 | [{"value": 65.7, "product": "ClC1=C(C(=C(N)C(=C1)F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,6-difluoro-3-methylaniline (15 g, 105 mmol) in acetic acid (80 mL) was heated to 70° C. and a solution of sulfuryl chloride (16.0 g, 115 mmol) in acetic acid (40 mL) was added dropwise over 20 minutes. The temperature was maintained for 3 hours, then cooled and concentrated. The residue taken into water... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | C(C)(=O)O | null | null | Cc1ccc(F)c(N)c1F.O=S(=O)(Cl)Cl>C(C)(=O)O>Cc1c(Cl)cc(F)c(N)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e2af558ef4584c13a57cdcb39236ea8c | C[Si](C)(C)Cl.Fc1cc(F)cc(Cl)c1>>C[Si](C)(C)c1c(F)cc(Cl)cc1F | C[Si](C)(C)Cl.FC=1C=C(C=C(C1)F)Cl.CN(CCN(C)C)C.C(CCC)[Li].[Cl-].[NH4+]>>ClC1=CC(=C(C(=C1)F)[Si](C)(C)C)F | Cl[Si:2]([CH3:1])([CH3:3])[CH3:4].[cH:5]1[c:6]([F:7])[cH:8][c:9]([Cl:10])[cH:11][c:12]1[F:13]>>[CH3:1][Si:2]([CH3:3])([CH3:4])[c:5]1[c:6]([F:7])[cH:8][c:9]([Cl:10])[cH:11][c:12]1[F:13] | C[Si](C)(C)Cl.Fc1cc(F)cc(Cl)c1 | C[Si](C)(C)c1c(F)cc(Cl)cc1F | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | f23ac93228f82637c1d8aa7bd66f17ca3b2108781d0ae51a0440944cf15dd599 | 62b25486659a0c3b8981491307676661488416039e4a601c8996c7216be92cf1 | c1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[F;D1;H0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9](-[F;D1;H0:10]):[c:11]>>[C;D1;H3:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3])(-[C;D1;H3:4])-[c;H0;D3;+0:8](:[c:6](-[F;D1;H0:5]):[c:7]):[c:9](-[F;D1;H0:10]):[c:11] | 89.6 | [{"value": 89.6, "product": "ClC1=CC(=C(C(=C1)F)[Si](C)(C)C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 3,5-difluoro-1-chlorobenzene (10.0 g, 67 mmol) and tetramethylethlenediamine (TMEDA; 7.8 g, 67 mmol) in THF (75 mL) at −75° C., was added n-butyl lithium (2.5M, 68 mmol) and the resulting solution stirred for 30 minutes. A solution of trimethylsilyl chloride (7.6 g, 70 mmol) in THF (15 mL) was added an... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Silyl protective group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | C1CCOC1 | null | 0.5 | C[Si](C)(C)Cl.Fc1cc(F)cc(Cl)c1>C1CCOC1>C[Si](C)(C)c1c(F)cc(Cl)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a53d013cd6db4dce9d7e555bc1afee8a | CN(C)C=O.C[Si](C)(C)c1c(F)cc(Cl)cc1F>>C[Si](C)(C)c1c(F)cc(Cl)c(C=O)c1F | ClC1=CC(=C(C(=C1)F)[Si](C)(C)C)F.CC1C(N(CCC1)C)(C)C.[Li].CN(C)C=O>>ClC1=CC(=C(C(=C1C=O)F)[Si](C)(C)C)F | CN(C)[CH:12]=[O:13].[CH3:1][Si:2]([CH3:3])([CH3:4])[c:5]1[c:6]([F:7])[cH:8][c:9]([Cl:10])[cH:11][c:14]1[F:15]>>[CH3:1][Si:2]([CH3:3])([CH3:4])[c:5]1[c:6]([F:7])[cH:8][c:9]([Cl:10])[c:11]([CH:12]=[O:13])[c:14]1[F:15] | CN(C)C=O.C[Si](C)(C)c1c(F)cc(Cl)cc1F | C[Si](C)(C)c1c(F)cc(Cl)c(C=O)c1F | null | null | C1CCOC1 | C-C Coupling | OtherReaction | aae5f0134f66d7b9e3ae1bdd9b3a75c7cb29a8908ff53e1c4658205cbcae8547 | f0bd75a0630092c31f21f61f4a015c77ae0dff14a0b742b4370d7a38fda490f7 | c1ccccc1 | C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2].[Cl;D1;H0:3]-[c:4](:[c:5]):[cH;D2;+0:6]:[c:7](-[F;D1;H0:8]):[c:9]>>[Cl;D1;H0:3]-[c:4](:[c:5]):[c;H0;D3;+0:6](-[CH;D2;+0:1]=[O;D1;H0:2]):[c:7](-[F;D1;H0:8]):[c:9] | 82.4 | [{"value": 82.4, "product": "ClC1=CC(=C(C(=C1C=O)F)[Si](C)(C)C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 1-chloro-3,5-difluoro-4-trimethylsilylbenzene (1.5 g, 6.8 mmol) in THF (10 mL) was added to a solution of lithium tetramethylpiperidine (14 mmol) in THF (15 mL) at −75° C. The solution was stirred for 2 hours then DMF (1.5 g, 20 mmol) was added and the solution allowed to warm to ambient temperature. The ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C1CCOC1 | null | 2 | CN(C)C=O.C[Si](C)(C)c1c(F)cc(Cl)cc1F>C1CCOC1>C[Si](C)(C)c1c(F)cc(Cl)c(C=O)c1F |
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