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-c3a75813d0b24864aa4f7cd526efd6aa | ord-7d96e6d24ff1482d847701b6c8e3136c | CCOC(=O)CC1c2ccccc2C(=O)N1CC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2ccccc2C1CC(=O)NC(=N)N | CC(C)([O-])C.[K+].[Cl-].NC(=[NH2+])N.C(C(C)C)N1C(C2=CC=CC=C2C1=O)CC(=O)OCC>>C(C(C)C)N1C(C2=CC=CC=C2C1=O)CC(=O)NC(=N)N | CCO[C:16]([CH2:15][CH:14]1[N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21)=[O:17].[NH2:18][C:19]([NH2:20])=[NH2+:21]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH:14]1[CH2:15][C:16](=[O:17])[NH:18][C:19](=[NH:20])[NH2:21] | CCOC(=O)CC1c2ccccc2C(=O)N1CC(C)C.NC(N)=[NH2+] | CC(C)CN1C(=O)c2ccccc2C1CC(=O)NC(=N)N | null | null | null | Acylation | OtherReaction | 2a0d0bb811d7d0d78ab0e0e0dd422aa0d95347cc6185304b02293baab0b54666 | bd0631f52f11765fc496c7945dc73cbc70f74ea4cf87d492a8fafb124a54fd13 | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[NH2+;D1:6]=[C;H0;D3;+0:7](-[NH2;D1;+0:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[NH2;D1;+0:6])=[NH;D1;+0:9] | 57.3 | [{"value": 57.3, "product": "C(C(C)C)N1C(C2=CC=CC=C2C1=O)CC(=O)NC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 24 | HOUR | N-[(2-Isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 1, starting with 5 g of potassium tert-butoxide, 5.2 g of guanidinium chloride and 2.5 g of ethyl (2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol1-yl)acetate. The reaction mixture is stirred at a temperature in the region o... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide.Primary amine | null | null | c1ccc2c(c1)C[NH]C2 | HO- | null | 20 | 24 | CCOC(=O)CC1c2ccccc2C(=O)N1CC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2ccccc2C1CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-af40e167416b4c3fa5b7ec94e55ef1e1 | CC(C)CN1C(=O)c2ccccc2C1O.CCOCC>>CCOC(=O)CC1c2ccccc2C(=O)N1CC(C)C | O.C(C)OCC.[H-].[Na+].OC1N(C(C2=CC=CC=C12)=O)CC(C)C>>C(C(C)C)N1C(C2=CC=CC=C2C1=O)CC(=O)OCC | [OH:5][CH:7]1[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14](=[O:15])[N:16]1[CH2:17][CH:18]([CH3:19])[CH3:20].[CH3:1][CH2:2][O:3][CH2:4][CH3:6]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14](=[O:15])[N:16]1[CH2:17][CH:18]([CH3:19])[CH3:20] | CC(C)CN1C(=O)c2ccccc2C1O.CCOCC | CCOC(=O)CC1c2ccccc2C(=O)N1CC(C)C | null | null | COCCOC | Heteroatom Alkylation and Arylation | OtherReaction | 48a0bd460ac260e177ffa262698d9e6ae802769dd91076aaf638df24b5a534e1 | 79b1dc52d3be254effebd4b18222e0510623f9682e37c200296c41f37c9f0926 | O=C1NCc2ccccc21 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9].[C:10]-[#8:11]-[CH2;D2;+0:12]-[CH3;D1;+0:13]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[CH2;D2;+0:13]-[C;H0;D3;+0:12](=[O;H0;D1;+0:9])-[#8:11]-[C:10] | null | [] | 0 | CELSIUS | null | null | 7.7 cm3 of triethyl phosphonoacetate are added dropwise, while keeping the temperature below 10° C., to a suspension of 1.6 g of 60% sodium hydride in 60 cm3 of 1,2-dimethoxyethane under an inert atmosphere and cooled to 0° C., with stirring. The reaction mixture is allowed to warm to a temperature in the region of 20°... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol | Ester | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | null | COCCOC | 0 | null | CC(C)CN1C(=O)c2ccccc2C1O.CCOCC>COCCOC>CCOC(=O)CC1c2ccccc2C(=O)N1CC(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7e460edd1088419d97082403be921997 | CC(C)CN1C(=O)c2ccccc2C1=O>>CC(C)CN1C(=O)c2ccccc2C1O | C(C(C)C)N1C(C=2C(C1=O)=CC=CC2)=O.O>>OC1N(C(C2=CC=CC=C12)=O)CC(C)C | [CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14]1=[O:15]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH:14]1[OH:15] | CC(C)CN1C(=O)c2ccccc2C1=O | CC(C)CN1C(=O)c2ccccc2C1O | null | null | [BH4-].[K+].CO | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1NCc2ccccc21 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 88.4 | [{"value": 88.4, "product": "OC1N(C(C2=CC=CC=C12)=O)CC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | 3-Hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 6.5 g of N-isobutylphthalimide in 60 cm3 of methanol and 1.7 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours and is then cooled to a temperature in the re... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | null | [BH4-].[K+].CO | 20 | 20 | CC(C)CN1C(=O)c2ccccc2C1=O>[BH4-].[K+].CO>CC(C)CN1C(=O)c2ccccc2C1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-597f172c828f4bd1b22ce94f8d6514bb | CC(C)CN.O=C1OC(=O)c2ccccc21>>CC(C)CN1C(=O)c2ccccc2C1=O | C(C(C)C)N.C1(C=2C(C(=O)O1)=CC=CC2)=O>>C(C(C)C)N1C(C=2C(C1=O)=CC=CC2)=O | [CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5].O1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14]1=[O:15]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14]1=[O:15] | CC(C)CN.O=C1OC(=O)c2ccccc21 | CC(C)CN1C(=O)c2ccccc2C1=O | null | null | C1(=CC=CC=C1)C | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[c:10](:[c:11]):[c:8](:[c:9])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | null | [] | 60 | CELSIUS | 2 | HOUR | A solution of 3.2 cm3 of isobutylamine in 3 cm3 of toluene is added to a suspension of 5.2 g of phthalic anhydride in 50 cm3 of toluene, with stirring. The reaction mixture is heated at a temperature in the region of 60° C. for 1 hour, and then at a temperature in the region of 100° C. for 2 hours. Dean-Stark apparatus... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | C1(=CC=CC=C1)C | 60 | 2 | CC(C)CN.O=C1OC(=O)c2ccccc21>C1(=CC=CC=C1)C>CC(C)CN1C(=O)c2ccccc2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b257c35695494c6886e15c8930a34970 | CCOC(=O)CC1c2ccccc2C(=O)N1CC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2ccccc2C1CC(=O)NC(=N)N | CC(C)([O-])C.[K+].[Cl-].NC(=[NH2+])N.C(C(C)C)N1C(C2=CC=CC=C2C1=O)CC(=O)OCC>>C(C(C)C)N1C(C2=CC=CC=C2C1=O)CC(=O)NC(=N)N | CCO[C:16]([CH2:15][CH:14]1[N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21)=[O:17].[NH2:18][C:19]([NH2:20])=[NH2+:21]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH:14]1[CH2:15][C:16](=[O:17])[NH:18][C:19](=[NH:20])[NH2:21] | CCOC(=O)CC1c2ccccc2C(=O)N1CC(C)C.NC(N)=[NH2+] | CC(C)CN1C(=O)c2ccccc2C1CC(=O)NC(=N)N | null | null | null | Acylation | OtherReaction | 2a0d0bb811d7d0d78ab0e0e0dd422aa0d95347cc6185304b02293baab0b54666 | bd0631f52f11765fc496c7945dc73cbc70f74ea4cf87d492a8fafb124a54fd13 | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[NH2+;D1:6]=[C;H0;D3;+0:7](-[NH2;D1;+0:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[NH2;D1;+0:6])=[NH;D1;+0:9] | 57.3 | [{"value": 57.3, "product": "C(C(C)C)N1C(C2=CC=CC=C2C1=O)CC(=O)NC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 40 | HOUR | (−)-N-[(2-Isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-y)acetyl]guanidine is prepared as described in Example 1, starting with 2.6 g of potassium tert-butoxide, 2.6 g of guanidinium chloride and 1.25 g of ethyl (−)-(2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol1-y)acetate. The reaction mixture is stirred at a temperature in the... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide.Primary amine | null | null | c1ccc2c(c1)C[NH]C2 | HO- | null | 20 | 40 | CCOC(=O)CC1c2ccccc2C(=O)N1CC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2ccccc2C1CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a066f5e8073d4560a443fc206aa48bfe | CCOC(=O)CC1c2ccccc2C(=O)N1CC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2ccccc2C1CC(=O)NC(=N)N | CC(C)([O-])C.[K+].[Cl-].NC(=[NH2+])N.C(C(C)C)N1C(C2=CC=CC=C2C1=O)CC(=O)OCC>>C(C(C)C)N1C(C2=CC=CC=C2C1=O)CC(=O)NC(=N)N | CCO[C:16]([CH2:15][CH:14]1[N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21)=[O:17].[NH2:18][C:19]([NH2:20])=[NH2+:21]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH:14]1[CH2:15][C:16](=[O:17])[NH:18][C:19](=[NH:20])[NH2:21] | CCOC(=O)CC1c2ccccc2C(=O)N1CC(C)C.NC(N)=[NH2+] | CC(C)CN1C(=O)c2ccccc2C1CC(=O)NC(=N)N | null | null | null | Acylation | OtherReaction | 2a0d0bb811d7d0d78ab0e0e0dd422aa0d95347cc6185304b02293baab0b54666 | bd0631f52f11765fc496c7945dc73cbc70f74ea4cf87d492a8fafb124a54fd13 | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[NH2+;D1:6]=[C;H0;D3;+0:7](-[NH2;D1;+0:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[NH2;D1;+0:6])=[NH;D1;+0:9] | 53.5 | [{"value": 53.5, "product": "C(C(C)C)N1C(C2=CC=CC=C2C1=O)CC(=O)NC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 40 | HOUR | (+)-N-[(2-Isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 1, starting with 2.0 g of potassium tert-butoxide, 2.1 g of guanidinium chloride and 1.0 g of ethyl (+)-(2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol1-y)acetate. The reaction mixture is stirred at a temperature in the... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide.Primary amine | null | null | c1ccc2c(c1)C[NH]C2 | HO- | null | 20 | 40 | CCOC(=O)CC1c2ccccc2C(=O)N1CC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2ccccc2C1CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b2dd0a2274da4fd9a4bbd7aca7dd0685 | CCCN1C(=O)c2ccccc2C1CC(=O)OCC.NC(N)=[NH2+]>>CCCN1C(=O)c2ccccc2C1CC(=O)NC(=N)N | CC(C)([O-])C.[K+].[Cl-].NC(=[NH2+])N.O=C1N(C(C2=CC=CC=C12)CC(=O)OCC)CCC>>O=C1N(C(C2=CC=CC=C12)CC(=O)NC(=N)N)CCC | CCO[C:15]([CH2:14][CH:13]1[N:4]([CH2:3][CH2:2][CH3:1])[C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21)=[O:16].[NH2+:17]=[C:18]([NH2:19])[NH2:20]>>[CH3:1][CH2:2][CH2:3][N:4]1[C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH:13]1[CH2:14][C:15](=[O:16])[NH:17][C:18](=[NH:19])[NH2:20] | CCCN1C(=O)c2ccccc2C1CC(=O)OCC.NC(N)=[NH2+] | CCCN1C(=O)c2ccccc2C1CC(=O)NC(=N)N | null | null | O | Acylation | OtherReaction | 09bfb108fb5b69552e7dcf8792cd0918114fd6e590129b579cec1dd12722db62 | e35fd5a84c281db4b9a756e738b7d6904fa44bd3c94329564f747de651850e99 | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[N;D1;H2:6]-[C;H0;D3;+0:7](=[NH2+;D1:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[N;D1;H2:6])=[NH;D1;+0:9] | 31.8 | [{"value": 31.8, "product": "O=C1N(C(C2=CC=CC=C12)CC(=O)NC(=N)N)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1 | HOUR | N-[(3-Oxo-2-propyl-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 1, starting with 3.9 g of potassium tert-butoxide, 3.3 g of guanidinium chloride and 1.8 g of ethyl (3-oxo-2-propyl-2,3-dihydro-1H-isoindol1-yl)acetate. The reaction mixture is stirred at a temperature in the region of ... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2 | HO- | O | 20 | 1 | CCCN1C(=O)c2ccccc2C1CC(=O)OCC.NC(N)=[NH2+]>O>CCCN1C(=O)c2ccccc2C1CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b899b9d8d8054722b2f738da334d7782 | CCCN1C(=O)c2ccccc2C1=O>>CCCN1C(=O)c2ccccc2C1O | C(CC)N1C(C=2C(C1=O)=CC=CC2)=O>>OC1N(C(C2=CC=CC=C12)=O)CCC | [CH3:1][CH2:2][CH2:3][N:4]1[C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]1=[O:14]>>[CH3:1][CH2:2][CH2:3][N:4]1[C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH:13]1[OH:14] | CCCN1C(=O)c2ccccc2C1=O | CCCN1C(=O)c2ccccc2C1O | null | null | [BH4-].[K+].CO | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1NCc2ccccc21 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 66 | [{"value": 66.0, "product": "OC1N(C(C2=CC=CC=C12)=O)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | 3-Hydroxy-2-propyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 1.5 g of N-propylphthalimide in 25 cm3 of methanol and 0.48 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours and is then cooled to a temperature in the regio... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | null | [BH4-].[K+].CO | 20 | 20 | CCCN1C(=O)c2ccccc2C1=O>[BH4-].[K+].CO>CCCN1C(=O)c2ccccc2C1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3070f13bd72545d38a8514b0b4057615 | CCOC(=O)CC1c2ccccc2C(=O)N1CC.NC(N)=[NH2+]>>CCN1C(=O)c2ccccc2C1CC(=O)NC(=N)N | CC(C)([O-])C.[K+].[Cl-].NC(=[NH2+])N.C(C)N1C(C2=CC=CC=C2C1=O)CC(=O)OCC>>C(C)N1C(C2=CC=CC=C2C1=O)CC(=O)NC(=N)N | CCO[C:14]([CH2:13][CH:12]1[N:3]([CH2:2][CH3:1])[C:4](=[O:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]21)=[O:15].[NH2:16][C:17]([NH2:18])=[NH2+:19]>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[CH:12]1[CH2:13][C:14](=[O:15])[NH:16][C:17](=[NH:18])[NH2:19] | CCOC(=O)CC1c2ccccc2C(=O)N1CC.NC(N)=[NH2+] | CCN1C(=O)c2ccccc2C1CC(=O)NC(=N)N | null | null | O | Acylation | OtherReaction | 2a0d0bb811d7d0d78ab0e0e0dd422aa0d95347cc6185304b02293baab0b54666 | bd0631f52f11765fc496c7945dc73cbc70f74ea4cf87d492a8fafb124a54fd13 | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[NH2+;D1:6]=[C;H0;D3;+0:7](-[NH2;D1;+0:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[NH2;D1;+0:6])=[NH;D1;+0:9] | 28 | [{"value": 28.0, "product": "C(C)N1C(C2=CC=CC=C2C1=O)CC(=O)NC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | N-[(2-Ethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 1, starting with 4.3 g of potassium tert-butoxide, 3.7 g of guanidinium chloride and 1.9 g of ethyl (2-ethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate. The reaction mixture is stirred at a temperature in the region of 2... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide.Primary amine | null | null | c1ccc2c(c1)C[NH]C2 | HO- | O | 20 | 20 | CCOC(=O)CC1c2ccccc2C(=O)N1CC.NC(N)=[NH2+]>O>CCN1C(=O)c2ccccc2C1CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a3a35763247f4b86877e29784c87ad69 | CCN1C(=O)c2ccccc2C1=O>>CCN1C(=O)c2ccccc2C1O | C(C)N1C(C=2C(C1=O)=CC=CC2)=O>>OC1N(C(C2=CC=CC=C12)=O)CC | [CH3:1][CH2:2][N:3]1[C:4](=[O:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[C:12]1=[O:13]>>[CH3:1][CH2:2][N:3]1[C:4](=[O:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[CH:12]1[OH:13] | CCN1C(=O)c2ccccc2C1=O | CCN1C(=O)c2ccccc2C1O | null | null | [BH4-].[K+].CO | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1NCc2ccccc21 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 47 | [{"value": 47.0, "product": "OC1N(C(C2=CC=CC=C12)=O)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | 3-Hydroxy-2-ethyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 4.0 g of N-ethylphthalimide in 20 cm3 of methanol and 1.2 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours and is then cooled to a temperature in the region o... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | null | [BH4-].[K+].CO | 20 | 20 | CCN1C(=O)c2ccccc2C1=O>[BH4-].[K+].CO>CCN1C(=O)c2ccccc2C1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fac0dd76dbd746cfa2286832699cea98 | CCOC(=O)CC1c2ccccc2C(=O)N1C(C)C.NC(N)=[NH2+]>>CC(C)N1C(=O)c2ccccc2C1CC(=O)NC(=N)N | CC(C)([O-])C.[K+].[Cl-].NC(=[NH2+])N.C(C)(C)N1C(C2=CC=CC=C2C1=O)CC(=O)OCC>>C(C)(C)N1C(C2=CC=CC=C2C1=O)CC(=O)NC(=N)N | CCO[C:15]([CH2:14][CH:13]1[N:4]([CH:2]([CH3:1])[CH3:3])[C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]21)=[O:16].[NH2:17][C:18]([NH2:19])=[NH2+:20]>>[CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH:13]1[CH2:14][C:15](=[O:16])[NH:17][C:18](=[NH:19])[NH2:20] | CCOC(=O)CC1c2ccccc2C(=O)N1C(C)C.NC(N)=[NH2+] | CC(C)N1C(=O)c2ccccc2C1CC(=O)NC(=N)N | null | null | O | Acylation | OtherReaction | 2a0d0bb811d7d0d78ab0e0e0dd422aa0d95347cc6185304b02293baab0b54666 | bd0631f52f11765fc496c7945dc73cbc70f74ea4cf87d492a8fafb124a54fd13 | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[NH2+;D1:6]=[C;H0;D3;+0:7](-[NH2;D1;+0:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[NH2;D1;+0:6])=[NH;D1;+0:9] | 6.8 | [{"value": 6.8, "product": "C(C)(C)N1C(C2=CC=CC=C2C1=O)CC(=O)NC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | N-[(2-Isopropyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 1, starting with 1.5 g of potassium tert-butoxide, 1.3 g of guanidinium chloride and 0.7 g of ethyl (2-isopropyl-3-oxo-2,3-dihydro-1H-isoindol1-yl)acetate. The reaction mixture is stirred at a temperature in the regi... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide.Primary amine | null | null | c1ccc2c(c1)C[NH]C2 | HO- | O | 20 | 20 | CCOC(=O)CC1c2ccccc2C(=O)N1C(C)C.NC(N)=[NH2+]>O>CC(C)N1C(=O)c2ccccc2C1CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2d56f0d53d9b445baa087d3657ed62bc | CC(C)N1C(=O)c2ccccc2C1=O>>CC(C)N1C(=O)c2ccccc2C1O | C(C)(C)N1C(C=2C(C1=O)=CC=CC2)=O>>OC1N(C(C2=CC=CC=C12)=O)C(C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[C:13]1=[O:14]>>[CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[CH:13]1[OH:14] | CC(C)N1C(=O)c2ccccc2C1=O | CC(C)N1C(=O)c2ccccc2C1O | null | null | [BH4-].[K+].CO | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1NCc2ccccc21 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 150.9 | [{"value": 150.9, "product": "OC1N(C(C2=CC=CC=C12)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | 3-Hydroxy-2-isopropyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 4.0 g of N-isopropylphthalimide in 20 cm3 of methanol and 1.1 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours and is then cooled to a temperature in the ... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | null | [BH4-].[K+].CO | 20 | 20 | CC(C)N1C(=O)c2ccccc2C1=O>[BH4-].[K+].CO>CC(C)N1C(=O)c2ccccc2C1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ecd23f1631294a80b9563074134158aa | O=C1c2ccccc2C(=O)N1CC1CC1>>O=C1c2ccccc2C(O)N1CC1CC1 | C1(CC1)CN1C(C=2C(C1=O)=CC=CC2)=O>>OC1N(C(C2=CC=CC=C12)=O)CC1CC1 | [O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH:13]1[CH2:14][CH2:15]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH:9]([OH:10])[N:11]1[CH2:12][CH:13]1[CH2:14][CH2:15]1 | O=C1c2ccccc2C(=O)N1CC1CC1 | O=C1c2ccccc2C(O)N1CC1CC1 | null | null | ClCCl.[BH4-].[K+].CO | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1c2ccccc2CN1CC1CC1 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 94.4 | [{"value": 94.4, "product": "OC1N(C(C2=CC=CC=C12)=O)CC1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | 3-Hydroxy-2-cyclopropylmethyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 4.3 g of N-cyclopropylmethylphthalimide in 40 cm3 of methanol and 1.2 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours and is then cooled to a tem... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC1 | null | ClCCl.[BH4-].[K+].CO | 20 | 20 | O=C1c2ccccc2C(=O)N1CC1CC1>ClCCl.[BH4-].[K+].CO>O=C1c2ccccc2C(O)N1CC1CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f97ef69472944c5491d3545fbca46f8e | NCC1CC1.O=C1OC(=O)c2ccccc21>>O=C1c2ccccc2C(=O)N1CC1CC1 | C1(C=2C(C(=O)O1)=CC=CC2)=O.C1(CC1)CN.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C1(CC1)CN1C(C=2C(C1=O)=CC=CC2)=O | [NH2:11][CH2:12][CH:13]1[CH2:14][CH2:15]1.O1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH:13]1[CH2:14][CH2:15]1 | NCC1CC1.O=C1OC(=O)c2ccccc21 | O=C1c2ccccc2C(=O)N1CC1CC1 | null | null | C1(=CC=CC=C1)C | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CC1CC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10](:[c:11])-[C;H0;D3;+0:5]-1=[O;D1;H0:4] | null | [] | 140 | CELSIUS | 16 | HOUR | N-Cyclopropylmethylphthalimide is prepared as described in Example 2, starting with 4 g of phthalic anhydride, 2.3 cm3 of cyclopropylmethylamine and a catalytic amount of para-toluenesulfonic acid in 40 cm3 of toluene. The reaction mixture is heated at a temperature in the region of 140° C. for 2 hours and is then cool... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC1 | HO- | C1(=CC=CC=C1)C | 140 | 16 | NCC1CC1.O=C1OC(=O)c2ccccc21>C1(=CC=CC=C1)C>O=C1c2ccccc2C(=O)N1CC1CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d79df0c8d25f43ae84c3534062ef46a2 | CCOC(=O)CC1c2ccccc2C(=O)N1Cc1ccccc1.NC(N)=[NH2+]>>N=C(N)NC(=O)CC1c2ccccc2C(=O)N1Cc1ccccc1 | [Na].[Na].C(C1=CC=CC=C1)N1C(C2=CC=CC=C2C1=O)CC(=O)OCC.[Cl-].NC(=[NH2+])N>>C(C1=CC=CC=C1)N1C(C2=CC=CC=C2C1=O)CC(=O)NC(=N)N | CCO[C:5](=[O:6])[CH2:7][CH:8]1[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15](=[O:16])[N:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[NH2:1][C:2]([NH2:3])=[NH2+:4]>>[NH:1]=[C:2]([NH2:3])[NH:4][C:5](=[O:6])[CH2:7][CH:8]1[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15](=[O:16])[N:17]1[CH2:18][c:19]1[cH:20][cH:... | CCOC(=O)CC1c2ccccc2C(=O)N1Cc1ccccc1.NC(N)=[NH2+] | N=C(N)NC(=O)CC1c2ccccc2C(=O)N1Cc1ccccc1 | null | null | C(C)O | Acylation | OtherReaction | 09bfb108fb5b69552e7dcf8792cd0918114fd6e590129b579cec1dd12722db62 | e35fd5a84c281db4b9a756e738b7d6904fa44bd3c94329564f747de651850e99 | O=C1c2ccccc2CN1Cc1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[N;D1;H2:6]-[C;H0;D3;+0:7](=[NH2+;D1:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[N;D1;H2:6])=[NH;D1;+0:9] | 57.6 | [{"value": 57.6, "product": "C(C1=CC=CC=C1)N1C(C2=CC=CC=C2C1=O)CC(=O)NC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1 | HOUR | 0.22 g of sodium is added to 20 cm3 of absolute ethanol under an inert atmosphere. After the sodium has totally disappeared, 0.94 g of guanidinium chloride is added. The reaction mixture is stirred under an inert atmosphere at a temperature in the region of 20° C. for 1 hour, followed by addition of a solution of 2 g o... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide | null | null | c1ccc2c(c1)C[NH]C2.c1ccccc1 | HO- | C(C)O | 20 | 1 | CCOC(=O)CC1c2ccccc2C(=O)N1Cc1ccccc1.NC(N)=[NH2+]>C(C)O>N=C(N)NC(=O)CC1c2ccccc2C(=O)N1Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-19c73cd70ac34a0cabf6a0b849c0f8e7 | CCOC(C)=O.O=C1c2ccccc2C(O)N1Cc1ccccc1>>CCOC(=O)CC1c2ccccc2C(=O)N1Cc1ccccc1 | C(C)(=O)OCC.[H-].[Na+].OC1N(C(C2=CC=CC=C12)=O)CC1=CC=CC=C1.O>>C(C1=CC=CC=C1)N1C(C2=CC=CC=C2C1=O)CC(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH3:6].O[CH:7]1[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14](=[O:15])[N:16]1[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[C:14](=[O:15])[N:16]1[CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23... | CCOC(C)=O.O=C1c2ccccc2C(O)N1Cc1ccccc1 | CCOC(=O)CC1c2ccccc2C(=O)N1Cc1ccccc1 | null | null | COCCOC | C-C Coupling | OtherReaction | f15997e17baabc84ad1f24d90439ac1e1bf9c091e3c8b61c6d23db78bb59ba96 | ec740fdba0adc3c659d56447beb3ee7a35d222db2ebbeacae7f761e1e85567b3 | O=C1c2ccccc2CN1Cc1ccccc1 | O-[CH;D3;+0:1]1-[#7:2](-[C:3])-[C:4](=[O;D1;H0:5])-[c:6]:[c:7]-1:[c:8].[C:9]-[#8:10]-[C:11](-[CH3;D1;+0:12])=[O;D1;H0:13]>>[C:3]-[#7:2]1-[C:4](=[O;D1;H0:5])-[c:6]:[c:7](:[c:8])-[CH;D3;+0:1]-1-[CH2;D2;+0:12]-[C:11](=[O;D1;H0:13])-[#8:10]-[C:9] | null | [] | 20 | CELSIUS | null | null | Ethyl (2-benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate is prepared as described in Example 2, starting with 3.2 9 of 60% sodium hydride in 200 cm3 of 1,2-dimethoxyethane, 16.4 cm3 of triethyl phosphonoacetate and 9.5 g of 3-hydroxy-2benzyl-2,3-dihydroisoindol-1-one. The mixture is refluxed for 18 hours and is then ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol | Ester | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccccc1 | HO- | COCCOC | 20 | null | CCOC(C)=O.O=C1c2ccccc2C(O)N1Cc1ccccc1>COCCOC>CCOC(=O)CC1c2ccccc2C(=O)N1Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-54e689850d1440c6b6611a0b94b7c5ed | O=C1c2ccccc2C(=O)N1Cc1ccccc1>>O=C1c2ccccc2C(O)N1Cc1ccccc1 | C(C1=CC=CC=C1)N1C(C=2C(C1=O)=CC=CC2)=O.O>>OC1N(C(C2=CC=CC=C12)=O)CC1=CC=CC=C1 | [O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH:9]([OH:10])[N:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | O=C1c2ccccc2C(O)N1Cc1ccccc1 | null | null | [BH4-].[K+].CO | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1c2ccccc2CN1Cc1ccccc1 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 92.4 | [{"value": 92.4, "product": "OC1N(C(C2=CC=CC=C12)=O)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | 3-Hydroxy-2-benzyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 10.2 g of N-benzylphthalimide in 100 cm3 of methanol and 2.6 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours and is then cooled to a temperature in the regi... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccccc1 | null | [BH4-].[K+].CO | 20 | 20 | O=C1c2ccccc2C(=O)N1Cc1ccccc1>[BH4-].[K+].CO>O=C1c2ccccc2C(O)N1Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-660e8600ee76448898112dcc0dde93fb | NCc1ccccc1.O=C1OC(=O)c2ccccc21>>O=C1c2ccccc2C(=O)N1Cc1ccccc1 | C1(C=2C(C(=O)O1)=CC=CC2)=O.C(C1=CC=CC=C1)N>>C(C1=CC=CC=C1)N1C(C=2C(C1=O)=CC=CC2)=O | [NH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.O1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | NCc1ccccc1.O=C1OC(=O)c2ccccc21 | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | null | null | C([O-])(O)=O.[Na+].C1(=CC=CC=C1)C | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1Cc1ccccc1 | [NH2;D1;+0:1]-[C:2]-[c:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[O;D1;H0:4]=[C;H0;D3;+0:5]1-[N;H0;D3;+0:1](-[C:2]-[c:3])-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11] | null | [] | 140 | CELSIUS | null | null | N-Benzylphthalimide is prepared as described in Example 2, starting with 10 g of phthalic anhydride, 7.3 cm3 of benzylamine and a catalytic amount of paratoluenesulfonic acid in 100 cm3 of toluene. The reaction mixture is heated at a temperature in the region of 140° C. for 3 hours and is then cooled to a temperature i... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccccc1 | HO- | C([O-])(O)=O.[Na+].C1(=CC=CC=C1)C | 140 | null | NCc1ccccc1.O=C1OC(=O)c2ccccc21>C([O-])(O)=O.[Na+].C1(=CC=CC=C1)C>O=C1c2ccccc2C(=O)N1Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cfa06a4cd86d493babc00b0e2b633b2d | CCOC(=O)CC1c2cc(C(C)(C)C)ccc2C(=O)N1CC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2ccc(C(C)(C)C)cc2C1CC(=O)NC(=N)N | [Na].[Cl-].NC(=[NH2+])N.C(C)(C)(C)C1=CC=C2C(N(C(C2=C1)CC(=O)OCC)CC(C)C)=O>>C(C)(C)(C)C1=CC=C2C(N(C(C2=C1)CC(=O)NC(=N)N)CC(C)C)=O | CCO[C:20]([CH2:19][CH:18]1[N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][c:17]21)=[O:21].[NH2:22][C:23]([NH2:24])=[NH2+:25]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][c:17]2[... | CCOC(=O)CC1c2cc(C(C)(C)C)ccc2C(=O)N1CC(C)C.NC(N)=[NH2+] | CC(C)CN1C(=O)c2ccc(C(C)(C)C)cc2C1CC(=O)NC(=N)N | null | null | C(C)O | Acylation | OtherReaction | 2a0d0bb811d7d0d78ab0e0e0dd422aa0d95347cc6185304b02293baab0b54666 | bd0631f52f11765fc496c7945dc73cbc70f74ea4cf87d492a8fafb124a54fd13 | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[NH2+;D1:6]=[C;H0;D3;+0:7](-[NH2;D1;+0:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[NH2;D1;+0:6])=[NH;D1;+0:9] | 68.1 | [{"value": 68.1, "product": "C(C)(C)(C)C1=CC=C2C(N(C(C2=C1)CC(=O)NC(=N)N)CC(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 16 | HOUR | N-[(6-tert-Butyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 9, starting with 20 cm3 of absolute ethanol, 0.37 g of sodium, 1.56 g of guanidinium chloride and 3.53 g of ethyl (6-tert-butyl-2-isobutyl-3oxo-2,3-dihydro-1H-isoindol-1-yl)acetate in 10 cm3 of absolute e... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide.Primary amine | null | null | c1ccc2c(c1)C[NH]C2 | HO- | C(C)O | 20 | 16 | CCOC(=O)CC1c2cc(C(C)(C)C)ccc2C(=O)N1CC(C)C.NC(N)=[NH2+]>C(C)O>CC(C)CN1C(=O)c2ccc(C(C)(C)C)cc2C1CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-892763597df54b7aa3735c07130c2bb0 | CC(C)CN1C(=O)c2cc(C(C)(C)C)ccc2C1O.CC(C)CN1C(=O)c2ccc(C(C)(C)C)cc2C1O.COCCOC>>CCOC(=O)CC1c2cc(C(C)(C)C)ccc2C(=O)N1CC(C)C.CCOC(=O)CC1c2ccc(C(C)(C)C)cc2C(=O)N1CC(C)C | C(C)(C)(C)C1=CC=C2C(N(C(C2=C1)=O)CC(C)C)O.C(C)(C)(C)C=1C=C2C(N(C(C2=CC1)=O)CC(C)C)O.O.COCCOC.[H-].[Na+]>>C(C)(C)(C)C1=CC=C2C(N(C(C2=C1)CC(=O)OCC)CC(C)C)=O.C(C)(C)(C)C=1C=C2C(N(C(C2=CC1)CC(=O)OCC)CC(C)C)=O | [CH:7]1([OH:29])[c:17]2[c:8]([cH:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[cH:15][cH:16]2)[C:18](=[O:19])[N:20]1[CH2:21][CH:22]([CH3:23])[CH3:24].[OH:5][CH:31]1[c:41]2[c:32]([cH:33][cH:34][c:35]([C:36]([CH3:37])([CH3:38])[CH3:39])[cH:40]2)[C:42](=[O:43])[N:44]1[CH2:45][CH:46]([CH3:47])[CH3:48].[CH3:1][O:3][CH2:30][C... | CC(C)CN1C(=O)c2cc(C(C)(C)C)ccc2C1O.CC(C)CN1C(=O)c2ccc(C(C)(C)C)cc2C1O.COCCOC | CCOC(=O)CC1c2cc(C(C)(C)C)ccc2C(=O)N1CC(C)C.CCOC(=O)CC1c2ccc(C(C)(C)C)cc2C(=O)N1CC(C)C | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 362a955bcbf55b12a94bfc1a8d73c33ade6a4f218422d9efb2e5766930dcc44e | c862efb9e1d3c5540cbd521d716baf4935af99206f23dafb24139e94d1655cd7 | O=C1NCc2ccccc21.O=C1NCc2ccccc21 | [CH3;D1;+0:1]-[O;H0;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[#8:5]-[CH3;D1;+0:6].[C:7]-[#7:8]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c;H0;D3;+0:11]2:[c:12]:[c:13]:[c:14]:[c:15]:[c;H0;D3;+0:16]:2-[CH;D3;+0:17]-1-[OH;D1;+0:18].[C:19]-[#7:20]1-[C;H0;D3;+0:21](=[O;D1;H0:22])-[c;H0;D3;+0:23]2:[c:24]:[c:25]:[c:26]:[c:27]:[c;H0;D3;+0:2... | null | [] | 20 | CELSIUS | null | null | Ethyl (5-tert-butyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate and ethyl (6-tert-butyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate are prepared as described in Example 2, starting with 2.9 g of 60% sodium hydride in 200 cm3 of 1,2-dimethoxyethane, 15.2 cm3 of triethyl phosphonoacetate and 9.6 g of ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amide.Tertiary amide.Secondary alcohol.Secondary alcohol | Ester.Ester.Tertiary amide.Tertiary amide | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | Other | C(C)(=O)OCC | 20 | null | CC(C)CN1C(=O)c2cc(C(C)(C)C)ccc2C1O.CC(C)CN1C(=O)c2ccc(C(C)(C)C)cc2C1O.COCCOC>C(C)(=O)OCC>CCOC(=O)CC1c2cc(C(C)(C)C)ccc2C(=O)N1CC(C)C.CCOC(=O)CC1c2ccc(C(C)(C)C)cc2C(=O)N1CC(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4ae975eb7c3f4dfbbf156b0a5ec3ab12 | CC(C)CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O.O>>CC(C)CN1C(=O)c2cc(C(C)(C)C)ccc2C1O.CC(C)CN1C(=O)c2ccc(C(C)(C)C)cc2C1O | O.C(C)(C)(C)C=1C=C2C(C(=O)N(C2=O)CC(C)C)=CC1>>C(C)(C)(C)C=1C=C2C(N(C(C2=CC1)=O)CC(C)C)O.C(C)(C)(C)C1=CC=C2C(N(C(C2=C1)=O)CC(C)C)O | [CH3:1][C:11]([c:10]1[cH:9][c:8]2[c:17]([cH:16][cH:15]1)[C:18](=[O:19])[N:5]([CH2:4][CH:21]([CH3:20])[CH3:22])[C:6]2=[O:7])([CH3:12])[CH3:31].[OH2:26]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[cH:15][cH:16][c:17]2[CH:18]1[OH:19].[CH3:20][CH:21]([CH3:22])[CH2... | CC(C)CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O.O | CC(C)CN1C(=O)c2cc(C(C)(C)C)ccc2C1O.CC(C)CN1C(=O)c2ccc(C(C)(C)C)cc2C1O | null | null | [BH4-].[K+].CO | Aromatic Heterocycle Formation | OtherReaction | 80e81150c5344eb5948e5ffa5d451e70555c1fccb2813d6b936dafb1decbe38f | 635345e99333bb5633c1a982d8704d75548f9c7be11489a084be362ff1b669ae | O=C1NCc2ccccc21.O=C1NCc2ccccc21 | [C;D1;H3:1]-[C;H0;D4;+0:2](-[CH3;D1;+0:3])(-[CH3;D1;+0:4])-[c:5]1:[c:6]:[c:7]:[c:8]2:[c:9](:[c:10]:1)-[C:11](=[O;D1;H0:12])-[#7:13](-[CH2;D2;+0:14]-[CH;D3;+0:15](-[C;D1;H3:16])-[C;D1;H3:17])-[C;H0;D3;+0:18]-2=[O;H0;D1;+0:19].[OH2;D0;+0:20]>>[C;D1;H3:21]-[C;H0;D4;+0:4](-[C;D1;H3:22])(-[C;D1;H3:23])-[c:24](:[c:25]):[c:26... | null | [] | 20 | CELSIUS | 19 | HOUR | 5-tert-Butyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one and 6-tert-butyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one are prepared as described in Example 1, starting with 10.4 g of 4-tert-butyl-N-isobutylphthalimide in 60 cm3 of methanol and 2.3 g of potassium borohydride. The reaction mixture is stirred at a te... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Tertiary amide.Secondary alcohol.Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | Other | [BH4-].[K+].CO | 20 | 19 | CC(C)CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O.O>[BH4-].[K+].CO>CC(C)CN1C(=O)c2cc(C(C)(C)C)ccc2C1O.CC(C)CN1C(=O)c2ccc(C(C)(C)C)cc2C1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-aa44b9e4c6cb47cdafae0e1281440de9 | CC(C)(C)c1ccc2c(c1)C(=O)OC2=O.CC(C)CN>>CC(C)CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O | C(C)(C)(C)C=1C=C2C(C(=O)OC2=O)=CC1.C(C(C)C)N.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C)(C)(C)C=1C=C2C(C(=O)N(C2=O)CC(C)C)=CC1 | O1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][c:17]2[C:18]1=[O:19].[CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][c:17]2[C:18]1=[O:19] | CC(C)(C)c1ccc2c(c1)C(=O)OC2=O.CC(C)CN | CC(C)CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O | null | null | C1(=CC=CC=C1)C | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[c:10](:[c:11]):[c:8](:[c:9])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | null | [] | 75 | CELSIUS | null | null | 4-tert-Butyl-N-isobutylphthalimide is prepared as described in Example 2, starting with 10 g of 4-tert-butylphthalic anhydride and 4.9 cm3 of isobutylamine in 100 cm3 of toluene. The reaction mixture is heated at a temperature in the region of 75° C. for 10 minutes, followed by addition of a catalytic amount of para-to... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | C1(=CC=CC=C1)C | 75 | null | CC(C)(C)c1ccc2c(c1)C(=O)OC2=O.CC(C)CN>C1(=CC=CC=C1)C>CC(C)CN1C(=O)c2ccc(C(C)(C)C)cc2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f2c638ea59514f86964a17e8b70d8d03 | CCOC(=O)CC1c2ccc(C(C)(C)C)cc2C(=O)N1CC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2cc(C(C)(C)C)ccc2C1CC(=O)NC(=N)N | [Na].[Cl-].NC(=[NH2+])N.C(C)(C)(C)C=1C=C2C(N(C(C2=CC1)CC(=O)OCC)CC(C)C)=O>>C(C)(C)(C)C=1C=C2C(N(C(C2=CC1)CC(=O)NC(=N)N)CC(C)C)=O | CCO[C:20]([CH2:19][CH:18]1[N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:6](=[O:7])[c:8]2[cH:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[cH:15][cH:16][c:17]21)=[O:21].[NH2:22][C:23]([NH2:24])=[NH2+:25]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][c:10]([C:11]([CH3:12])([CH3:13])[CH3:14])[cH:15][cH:16][c:17]2[... | CCOC(=O)CC1c2ccc(C(C)(C)C)cc2C(=O)N1CC(C)C.NC(N)=[NH2+] | CC(C)CN1C(=O)c2cc(C(C)(C)C)ccc2C1CC(=O)NC(=N)N | null | null | C(C)O | Acylation | OtherReaction | 2a0d0bb811d7d0d78ab0e0e0dd422aa0d95347cc6185304b02293baab0b54666 | bd0631f52f11765fc496c7945dc73cbc70f74ea4cf87d492a8fafb124a54fd13 | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[NH2+;D1:6]=[C;H0;D3;+0:7](-[NH2;D1;+0:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[NH2;D1;+0:6])=[NH;D1;+0:9] | 58.5 | [{"value": 58.5, "product": "C(C)(C)(C)C=1C=C2C(N(C(C2=CC1)CC(=O)NC(=N)N)CC(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 18 | HOUR | N-[(5-tert-Butyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 9, starting with 10 cm3 of absolute ethanol, 0.19 g of sodium, 0.80 g of guanidinium chloride and 1.81 g of ethyl (5-tert-butyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate in 10 cm3 of absolute ... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide.Primary amine | null | null | c1ccc2c(c1)C[NH]C2 | HO- | C(C)O | 20 | 18 | CCOC(=O)CC1c2ccc(C(C)(C)C)cc2C(=O)N1CC(C)C.NC(N)=[NH2+]>C(C)O>CC(C)CN1C(=O)c2cc(C(C)(C)C)ccc2C1CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-59ecbc226b2140e2806ae1c04f1b3579 | CCOC(=O)CC1c2ccc(Cl)cc2C(=O)N1CC(C)C.NC(N)=[NH2+].[Cl-]>>CC(C)CN1C(=O)c2cc(Cl)ccc2C1CC(=O)NC(=N)N.CC(C)CN1C(=O)c2ccc(Cl)cc2C1CC(=O)NC(=N)N | [Cl-].NC(=[NH2+])N.ClC=1C=C2C(N(C(C2=CC1)CC(=O)OCC)CC(C)C)=O.[Na]>>ClC=1C=C2C(N(C(C2=CC1)CC(=O)NC(=N)N)CC(C)C)=O.ClC1=CC=C2C(N(C(C2=C1)CC(=O)NC(=N)N)CC(C)C)=O | [CH3:1][CH:2]([CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][c:10]([Cl:11])[cH:12][cH:13][c:14]2[CH:15]1[CH2:16][C:17]([O:18][CH2:35][CH3:33])=[O:29])[CH3:24].[NH2:19][C:20](=[NH2+:27])[NH2:43].[Cl-:34]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][c:10]([Cl:11])[cH:12][cH:13][c:14]2[CH:15]1[CH2:16][C:17](=[O:1... | CCOC(=O)CC1c2ccc(Cl)cc2C(=O)N1CC(C)C.NC(N)=[NH2+].[Cl-] | CC(C)CN1C(=O)c2cc(Cl)ccc2C1CC(=O)NC(=N)N.CC(C)CN1C(=O)c2ccc(Cl)cc2C1CC(=O)NC(=N)N | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 7c82fcc1e74bd5cbdb5491325bc7c3599033fa46b7fea7b0b39f8423f90c3bf1 | 0bacb8cb440162b22f0fcc771f33b210c66e45c5ea397677a82721c07267effe | O=C1NCc2ccccc21.O=C1NCc2ccccc21 | [C;D1;H3:1]-[CH;D3;+0:2](-[CH3;D1;+0:3])-[C:4]-[#7:5](-[C:6]-[C:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[O;H0;D2;+0:10]-[CH2;D2;+0:11]-[CH3;D1;+0:12])-[C:13]=[O;D1;H0:14].[Cl-;H0;D0:15].[NH2+;D1:16]=[C;H0;D3;+0:17](-[NH2;D1;+0:18])-[NH2;D1;+0:19]>>[#7:20]-[C:21](-[N;D1;H2:22])=[NH;D1;+0:19].[C:23]-[C:24]1-[N;H0;D3;+0:16](-[... | null | [] | 20 | CELSIUS | 18 | HOUR | N-[(5-Chloro-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine and N-[(6chloro-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine are prepared as described in Example 9, starting with 20 cm3 of absolute ethanol, 0.35 g of sodium, 1.46 g of guanidinium chloride and 3.1 g of ethyl (5-chloro-2-iso... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Aromatic halide.Secondary amide.Secondary amide.Tertiary amide.Primary amine.Primary amine | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | null | C(C)O | 20 | 18 | CCOC(=O)CC1c2ccc(Cl)cc2C(=O)N1CC(C)C.NC(N)=[NH2+].[Cl-]>C(C)O>CC(C)CN1C(=O)c2cc(Cl)ccc2C1CC(=O)NC(=N)N.CC(C)CN1C(=O)c2ccc(Cl)cc2C1CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e16c58598d4842e38ce7bee11878f750 | CC(C)CN1C(=O)c2cc(Cl)ccc2C1O.CC(C)CN1C(=O)c2ccc(Cl)cc2C1O.COCCOC>>CCOC(=O)CC1c2cc(Cl)ccc2C(=O)N1CC(C)C.CCOC(=O)CC1c2ccc(Cl)cc2C(=O)N1CC(C)C | ClC1=CC=C2C(N(C(C2=C1)=O)CC(C)C)O.[H-].[Na+].ClC=1C=C2C(N(C(C2=CC1)=O)CC(C)C)O.O.COCCOC>>ClC=1C=C2C(N(C(C2=CC1)CC(=O)OCC)CC(C)C)=O.ClC1=CC=C2C(N(C(C2=C1)CC(=O)OCC)CC(C)C)=O | [CH:7]1([OH:26])[c:14]2[c:8]([cH:9][c:10]([Cl:11])[cH:12][cH:13]2)[C:15](=[O:16])[N:17]1[CH2:18][CH:19]([CH3:21])[CH3:27].[OH:5][CH:28]1[c:35]2[c:29]([cH:30][cH:31][c:32]([Cl:33])[cH:34]2)[C:36](=[O:37])[N:38]1[CH2:39][CH:40]([CH3:41])[CH3:42].[CH2:1]([O:3][CH3:2])[CH2:25][O:24][CH3:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5]... | CC(C)CN1C(=O)c2cc(Cl)ccc2C1O.CC(C)CN1C(=O)c2ccc(Cl)cc2C1O.COCCOC | CCOC(=O)CC1c2cc(Cl)ccc2C(=O)N1CC(C)C.CCOC(=O)CC1c2ccc(Cl)cc2C(=O)N1CC(C)C | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 362a955bcbf55b12a94bfc1a8d73c33ade6a4f218422d9efb2e5766930dcc44e | c862efb9e1d3c5540cbd521d716baf4935af99206f23dafb24139e94d1655cd7 | O=C1NCc2ccccc21.O=C1NCc2ccccc21 | [C;D1;H3:1]-[CH;D3;+0:2](-[CH3;D1;+0:3])-[C:4]-[#7:5]1-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c:11]:[c:12]:[c;H0;D3;+0:13]:2-[CH;D3;+0:14]-1-[OH;D1;+0:15].[CH3;D1;+0:16]-[#8:17]-[CH2;D2;+0:18]-[CH2;D2;+0:19]-[O;H0;D2;+0:20]-[CH3;D1;+0:21].[C:22]-[#7:23]1-[C;H0;D3;+0:24](=[O;D1;H0:25])-[c;H0;D3;+0:26... | null | [] | 20 | CELSIUS | null | null | Ethyl (5-chloro-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate and ethyl (6-chloro-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate are prepared as described in Example 2, starting with 4 g of 60% sodium hydride in 200 cm3 of 1,2-dimethoxyethane, 20.3 cm3 of triethyl phosphonoacetate and 12 g of 5-chloro-3-... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amide.Tertiary amide.Secondary alcohol.Secondary alcohol | Ester.Ester.Tertiary amide.Tertiary amide | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | Other | C(C)(=O)OCC | 20 | null | CC(C)CN1C(=O)c2cc(Cl)ccc2C1O.CC(C)CN1C(=O)c2ccc(Cl)cc2C1O.COCCOC>C(C)(=O)OCC>CCOC(=O)CC1c2cc(Cl)ccc2C(=O)N1CC(C)C.CCOC(=O)CC1c2ccc(Cl)cc2C(=O)N1CC(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3b0e4232745a415f84ee421773f9dc6f | CC(C)CN1C(=O)c2ccc(Cl)cc2C1=O>>CC(C)CN1C(=O)c2ccc(Cl)cc2C1O | ClC=1C=C2C(C(=O)N(C2=O)CC(C)C)=CC1.O>>ClC=1C=C2C(N(C(C2=CC1)=O)CC(C)C)O | [CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]2[C:15]1=[O:16]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]2[CH:15]1[OH:16] | CC(C)CN1C(=O)c2ccc(Cl)cc2C1=O | CC(C)CN1C(=O)c2ccc(Cl)cc2C1O | null | null | [BH4-].[K+].CO | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1NCc2ccccc21 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | null | [] | 20 | CELSIUS | 20 | HOUR | 5-Chloro-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one and 6-chloro-3-hydroxy-2isobutyl-2,3-dihydroinsoindol-1-one are prepared as described in Example 1, starting with 12 g of 4-chloro-N-isobutylphthalimide in 100 cm3 of methanol and 3 g of potassium borohydride. The reaction mixture is stirred at a temperature in th... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | null | [BH4-].[K+].CO | 20 | 20 | CC(C)CN1C(=O)c2ccc(Cl)cc2C1=O>[BH4-].[K+].CO>CC(C)CN1C(=O)c2ccc(Cl)cc2C1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e924a00a32eb4943afc624d45db47c6f | CC(C)CN.O=C1OC(=O)c2cc(Cl)ccc21>>CC(C)CN1C(=O)c2ccc(Cl)cc2C1=O | ClC=1C=C2C(C(=O)OC2=O)=CC1.C(C(C)C)N.C1(=CC=C(C=C1)S(=O)(=O)O)C>>ClC=1C=C2C(C(=O)N(C2=O)CC(C)C)=CC1 | [CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5].O1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]2[C:15]1=[O:16]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]2[C:15]1=[O:16] | CC(C)CN.O=C1OC(=O)c2cc(Cl)ccc21 | CC(C)CN1C(=O)c2ccc(Cl)cc2C1=O | null | null | C([O-])(O)=O.[Na+].C1(=CC=CC=C1)C | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[c:10](:[c:11]):[c:8](:[c:9])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | null | [] | 140 | CELSIUS | null | null | 4-Chloro-N-isobutylphthalimide is prepared as described in Example 2, starting with 10 g of 4-chlorophthalic anhydride, 5.4 cm3 of isobutylamine and a catalytic amount of para-toluenesulfonic acid in 100 cm3 of toluene. The reaction mixture is heated at a temperature in the region of 140° C. for 16 hours and is then co... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | C([O-])(O)=O.[Na+].C1(=CC=CC=C1)C | 140 | null | CC(C)CN.O=C1OC(=O)c2cc(Cl)ccc21>C([O-])(O)=O.[Na+].C1(=CC=CC=C1)C>CC(C)CN1C(=O)c2ccc(Cl)cc2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5c5a65e00f3b41589c35f5315322a40f | CCOC(=O)CC1c2cc(Br)ccc2C(=O)N1CC(C)C.CCOC(=O)CC1c2ccc(Br)cc2C(=O)N1CC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2cc(Br)ccc2C1CC(=O)NC(=N)N.CC(C)CN1C(=O)c2ccc(Br)cc2C1CC(=O)NC(=N)N | BrC1=CC=C2C(N(C(C2=C1)CC(=O)OCC)CC(C)C)=O.[Cl-].NC(=[NH2+])N.BrC=1C=C2C(N(C(C2=CC1)CC(=O)OCC)CC(C)C)=O.[Na]>>BrC1=CC=C2C(N(C(C2=C1)CC(=O)NC(=N)N)CC(C)C)=O.BrC=1C=C2C(N(C(C2=CC1)CC(=O)NC(=N)N)CC(C)C)=O | CCO[C:20]([CH2:16][CH:15]1[N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:6](=[O:7])[c:14]2[c:8]1[cH:9][c:10]([Br:11])[cH:12][cH:13]2)=[O:18].C(O[C:39]([CH2:38][CH:37]1[N:27]([CH2:26][CH:24]([CH3:23])[CH3:25])[C:28](=[O:29])[c:36]2[c:30]1[cH:31][cH:32][c:33]([Br:34])[cH:35]2)=[O:40])[CH3:17].[NH2:19][C:42]([NH2:21])=[NH2+:41]>>... | CCOC(=O)CC1c2cc(Br)ccc2C(=O)N1CC(C)C.CCOC(=O)CC1c2ccc(Br)cc2C(=O)N1CC(C)C.NC(N)=[NH2+] | CC(C)CN1C(=O)c2cc(Br)ccc2C1CC(=O)NC(=N)N.CC(C)CN1C(=O)c2ccc(Br)cc2C1CC(=O)NC(=N)N | null | null | O.C(C)OCC.C(C)O | Acylation | OtherReaction | 58c7bbe22abce425286dc7c77ea04f5fe7262ea222c8df00fb60d9de48138947 | c13b7a4604f90d6b297071920a60f6e92464931ecb3ae9d252f9bb3cb252eb66 | O=C1NCc2ccccc21.O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH2;D2;+0:3]-[CH;D3;+0:4]1-[#7:5](-[C:6])-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c;H0;D3;+0:9]2:[c:10]:[c:11]:[c:12]:[c:13]:[c;H0;D3;+0:14]:2-1.[C:15]-[#7:16]1-[C;H0;D3;+0:17](=[O;D1;H0:18])-[c;H0;D3;+0:19]2:[c:20]:[c:21]:[c:22]:[c:23]:[c;H0;D3;+0:24]:2-[CH;D3;+0:25]-1-[C:26]-[C;H0;D3;+0:2... | null | [] | 20 | CELSIUS | 16 | HOUR | N-[(5-Bromo-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine and N-[(6-bromo-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine are prepared as described in Example 9, starting with 30 cm3 of absolute ethanol, 0.36 g of sodium, 1.5 g of guanidinium chloride and 3.7 g of ethyl (5-bromo-2-isobut... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester.Ester.Tertiary amide.Tertiary amide | Secondary amide.Secondary amide.Tertiary amide.Tertiary amide.Primary amine.Primary amine | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | HO- | O.C(C)OCC.C(C)O | 20 | 16 | CCOC(=O)CC1c2cc(Br)ccc2C(=O)N1CC(C)C.CCOC(=O)CC1c2ccc(Br)cc2C(=O)N1CC(C)C.NC(N)=[NH2+]>O.C(C)OCC.C(C)O>CC(C)CN1C(=O)c2cc(Br)ccc2C1CC(=O)NC(=N)N.CC(C)CN1C(=O)c2ccc(Br)cc2C1CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3008eb1ac514440086fb77b46c5fc459 | CC(C)CN1C(=O)c2cc(Br)ccc2C1O.CC(C)CN1C(=O)c2ccc(Br)cc2C1O.COCCOC>>CCOC(=O)CC1c2cc(Br)ccc2C(=O)N1CC(C)C.CCOC(=O)CC1c2ccc(Br)cc2C(=O)N1CC(C)C | BrC1=CC=C2C(N(C(C2=C1)=O)CC(C)C)O.COCCOC.[H-].[Na+].O.BrC=1C=C2C(N(C(C2=CC1)=O)CC(C)C)O>>BrC1=CC=C2C(N(C(C2=C1)CC(=O)OCC)CC(C)C)=O.BrC=1C=C2C(N(C(C2=CC1)CC(=O)OCC)CC(C)C)=O | [CH:7]1([OH:26])[c:14]2[c:8]([cH:9][c:10]([Br:11])[cH:12][cH:13]2)[C:15](=[O:16])[N:17]1[CH2:18][CH:19]([CH3:21])[CH3:27].[OH:5][CH:28]1[c:35]2[c:29]([cH:30][cH:31][c:32]([Br:33])[cH:34]2)[C:36](=[O:37])[N:38]1[CH2:39][CH:40]([CH3:41])[CH3:42].[CH2:1]([O:3][CH3:2])[CH2:25][O:24][CH3:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5]... | CC(C)CN1C(=O)c2cc(Br)ccc2C1O.CC(C)CN1C(=O)c2ccc(Br)cc2C1O.COCCOC | CCOC(=O)CC1c2cc(Br)ccc2C(=O)N1CC(C)C.CCOC(=O)CC1c2ccc(Br)cc2C(=O)N1CC(C)C | null | null | null | Acylation | OtherReaction | 362a955bcbf55b12a94bfc1a8d73c33ade6a4f218422d9efb2e5766930dcc44e | c862efb9e1d3c5540cbd521d716baf4935af99206f23dafb24139e94d1655cd7 | O=C1NCc2ccccc21.O=C1NCc2ccccc21 | [C;D1;H3:1]-[CH;D3;+0:2](-[CH3;D1;+0:3])-[C:4]-[#7:5]1-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c:11]:[c:12]:[c;H0;D3;+0:13]:2-[CH;D3;+0:14]-1-[OH;D1;+0:15].[CH3;D1;+0:16]-[#8:17]-[CH2;D2;+0:18]-[CH2;D2;+0:19]-[O;H0;D2;+0:20]-[CH3;D1;+0:21].[C:22]-[#7:23]1-[C;H0;D3;+0:24](=[O;D1;H0:25])-[c;H0;D3;+0:26... | null | [] | 20 | CELSIUS | null | null | Ethyl (5-bromo-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate and ethyl (6-bromo-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate are prepared as described in Example 2, starting with 5.0 g of 60% sodium hydride in 250 cm3 of 1,2-dimethoxyethane, 24.8 cm3 of triethyl phosphonoacetate and 23.7 g of 5-bromo-3... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amide.Tertiary amide.Secondary alcohol.Secondary alcohol | Ester.Ester.Tertiary amide.Tertiary amide | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | Other | null | 20 | null | CC(C)CN1C(=O)c2cc(Br)ccc2C1O.CC(C)CN1C(=O)c2ccc(Br)cc2C1O.COCCOC>>CCOC(=O)CC1c2cc(Br)ccc2C(=O)N1CC(C)C.CCOC(=O)CC1c2ccc(Br)cc2C(=O)N1CC(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-afff836b6a81496ba9bb331b596140e9 | CC(C)CN1C(=O)c2ccc(Br)cc2C1=O>>CC(C)CN1C(=O)c2ccc(Br)cc2C1O | BrC=1C=C2C(C(=O)N(C2=O)CC(C)C)=CC1.O>>BrC=1C=C2C(N(C(C2=CC1)=O)CC(C)C)O | [CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]2[C:15]1=[O:16]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]2[CH:15]1[OH:16] | CC(C)CN1C(=O)c2ccc(Br)cc2C1=O | CC(C)CN1C(=O)c2ccc(Br)cc2C1O | null | null | [BH4-].[K+].CO | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1NCc2ccccc21 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 99.7 | [{"value": 99.7, "product": "BrC=1C=C2C(N(C(C2=CC1)=O)CC(C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 16 | HOUR | 5-Bromo-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one and 6-bromo-3-hydroxy-2-isobutyl-2,3-dihydroinsoindol-1-one are prepared as described in Example 1, starting with 23.6 g of 4-bromo-N-isobutylphthalimide in 200 cm3 of methanol and 4.5 g of potassium borohydride. The reaction mixture is stirred at a temperature in ... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | null | [BH4-].[K+].CO | 20 | 16 | CC(C)CN1C(=O)c2ccc(Br)cc2C1=O>[BH4-].[K+].CO>CC(C)CN1C(=O)c2ccc(Br)cc2C1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-db135124f2e94d89be47ea9aaeddff43 | CC(C)CN.O=C1OC(=O)c2cc(Br)ccc21>>CC(C)CN1C(=O)c2ccc(Br)cc2C1=O | BrC=1C=C2C(C(=O)OC2=O)=CC1.C(C(C)C)N.C1(=CC=C(C=C1)S(=O)(=O)O)C>>BrC=1C=C2C(C(=O)N(C2=O)CC(C)C)=CC1 | [CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5].O1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]2[C:15]1=[O:16]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][c:14]2[C:15]1=[O:16] | CC(C)CN.O=C1OC(=O)c2cc(Br)ccc21 | CC(C)CN1C(=O)c2ccc(Br)cc2C1=O | null | null | C1(=CC=CC=C1)C | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[c:10](:[c:11]):[c:8](:[c:9])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | null | [] | 140 | CELSIUS | null | null | 4-Bromo-N-isobutylphthalimide is prepared as described in Example 2, starting with 20 g of 4-bromophthalic anhydride, 9.2 cm3 of isobutylamine and a catalytic amount of para-toluenesulfonic acid in 200 cm3 of toluene. The reaction mixture is heated at a temperature in the region of 140° C. for 6 hours and is then coole... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | C1(=CC=CC=C1)C | 140 | null | CC(C)CN.O=C1OC(=O)c2cc(Br)ccc21>C1(=CC=CC=C1)C>CC(C)CN1C(=O)c2ccc(Br)cc2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a48b7957df4a4c8b9c68670db0bcf645 | CCOC(=O)CC1c2ccc(C(F)(F)F)cc2C(=O)N1CC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2cc(C(F)(F)F)ccc2C1CC(=O)NC(=N)N | [Na].[Cl-].NC(=[NH2+])N.FC(C=1C=C2C(N(C(C2=CC1)CC(=O)OCC)CC(C)C)=O)(F)F>>FC(C=1C=C2C(N(C(C2=CC1)CC(=O)NC(=N)N)CC(C)C)=O)(F)F | CCO[C:20]([CH2:19][CH:18]1[N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:6](=[O:7])[c:8]2[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16][c:17]21)=[O:21].[NH2:22][C:23]([NH2:24])=[NH2+:25]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16][c:17]2[CH:18]1[CH2:... | CCOC(=O)CC1c2ccc(C(F)(F)F)cc2C(=O)N1CC(C)C.NC(N)=[NH2+] | CC(C)CN1C(=O)c2cc(C(F)(F)F)ccc2C1CC(=O)NC(=N)N | null | null | C(C)OCC.C(C)O | Acylation | OtherReaction | 2a0d0bb811d7d0d78ab0e0e0dd422aa0d95347cc6185304b02293baab0b54666 | bd0631f52f11765fc496c7945dc73cbc70f74ea4cf87d492a8fafb124a54fd13 | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[NH2+;D1:6]=[C;H0;D3;+0:7](-[NH2;D1;+0:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[NH2;D1;+0:6])=[NH;D1;+0:9] | 17.6 | [{"value": 17.6, "product": "FC(C=1C=C2C(N(C(C2=CC1)CC(=O)NC(=N)N)CC(C)C)=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 16 | HOUR | N-[2-(2-Isobutyl-3-oxo-5-trifluoromethyl-2,3-dihydro-1H-isoindol-1-yl)-acetyl]-guanidine is prepared as described in Example 9, starting with 10 cm3 of absolute ethanol, 0.19 g of sodium, 0.78 g of guanidinium chloride and 1.86 g of ethyl (5-trifluoromethyl-2-isobutyl-3-oxo-2,3-dihyrdo-1H-isoindol-1-yl)acetate in 10 cm... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide.Primary amine | null | null | c1ccc2c(c1)C[NH]C2 | HO- | C(C)OCC.C(C)O | 20 | 16 | CCOC(=O)CC1c2ccc(C(F)(F)F)cc2C(=O)N1CC(C)C.NC(N)=[NH2+]>C(C)OCC.C(C)O>CC(C)CN1C(=O)c2cc(C(F)(F)F)ccc2C1CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-11c04c56488c4ee4b02881805dd5137c | CCOC(=O)CC1c2cc(C(F)(F)F)ccc2C(=O)N1CC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2ccc(C(F)(F)F)cc2C1CC(=O)NC(=N)N | [Na].[Cl-].NC(=[NH2+])N.FC(C1=CC=C2C(N(C(C2=C1)CC(=O)OCC)CC(C)C)=O)(F)F>>C(C(C)C)N1C(C2=CC(=CC=C2C1=O)C(F)(F)F)CC(=O)NC(=N)N | CCO[C:20]([CH2:19][CH:18]1[N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][c:17]21)=[O:21].[NH2:22][C:23]([NH2:24])=[NH2+:25]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][c:17]2[CH:18]1[CH2:... | CCOC(=O)CC1c2cc(C(F)(F)F)ccc2C(=O)N1CC(C)C.NC(N)=[NH2+] | CC(C)CN1C(=O)c2ccc(C(F)(F)F)cc2C1CC(=O)NC(=N)N | null | null | C(C)OCC.C(C)O | Acylation | OtherReaction | 2a0d0bb811d7d0d78ab0e0e0dd422aa0d95347cc6185304b02293baab0b54666 | bd0631f52f11765fc496c7945dc73cbc70f74ea4cf87d492a8fafb124a54fd13 | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[NH2+;D1:6]=[C;H0;D3;+0:7](-[NH2;D1;+0:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[NH2;D1;+0:6])=[NH;D1;+0:9] | 7.6 | [{"value": 7.6, "product": "C(C(C)C)N1C(C2=CC(=CC=C2C1=O)C(F)(F)F)CC(=O)NC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 16 | HOUR | N-[2-(2-Isobutyl-3-oxo-6-trifluoromethyl-2,3-dihydro-1H-isoindol-1-yl)-acetyl]-guanidine is prepared as described in Example 9, starting with 10 cm3 of absolute ethanol, 0.13 g of sodium, 0.52 g of guanidinium chloride and 1.25 g of ethyl (6-trifluoromethyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate in 10 cm... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide.Primary amine | null | null | c1ccc2c(c1)C[NH]C2 | HO- | C(C)OCC.C(C)O | 20 | 16 | CCOC(=O)CC1c2cc(C(F)(F)F)ccc2C(=O)N1CC(C)C.NC(N)=[NH2+]>C(C)OCC.C(C)O>CC(C)CN1C(=O)c2ccc(C(F)(F)F)cc2C1CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b911b6e30eac40c5be3c86438d8fe792 | CC(C)CN1C(=O)c2cc(C(F)(F)F)ccc2C1O.CC(C)CN1C(=O)c2ccc(C(F)(F)F)cc2C1O.COCCOC>>CCOC(=O)CC1c2cc(C(F)(F)F)ccc2C(=O)N1CC(C)C.CCOC(=O)CC1c2ccc(C(F)(F)F)cc2C(=O)N1CC(C)C | FC(C1=CC=C2C(N(C(C2=C1)=O)CC(C)C)O)(F)F.COCCOC.[H-].[Na+].O.FC(C=1C=C2C(N(C(C2=CC1)=O)CC(C)C)O)(F)F>>FC(C1=CC=C2C(N(C(C2=C1)CC(=O)OCC)CC(C)C)=O)(F)F.FC(C=1C=C2C(N(C(C2=CC1)CC(=O)OCC)CC(C)C)=O)(F)F | [CH:7]1([OH:29])[c:17]2[c:8]([cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[C:18](=[O:19])[N:20]1[CH2:21][CH:22]([CH3:23])[CH3:24].[OH:5][CH:31]1[c:41]2[c:32]([cH:33][cH:34][c:35]([C:36]([F:37])([F:38])[F:39])[cH:40]2)[C:42](=[O:43])[N:44]1[CH2:45][CH:46]([CH3:47])[CH3:48].[CH3:1][O:3][CH2:30][CH2:28][O:27]... | CC(C)CN1C(=O)c2cc(C(F)(F)F)ccc2C1O.CC(C)CN1C(=O)c2ccc(C(F)(F)F)cc2C1O.COCCOC | CCOC(=O)CC1c2cc(C(F)(F)F)ccc2C(=O)N1CC(C)C.CCOC(=O)CC1c2ccc(C(F)(F)F)cc2C(=O)N1CC(C)C | null | null | null | Acylation | OtherReaction | 362a955bcbf55b12a94bfc1a8d73c33ade6a4f218422d9efb2e5766930dcc44e | c862efb9e1d3c5540cbd521d716baf4935af99206f23dafb24139e94d1655cd7 | O=C1NCc2ccccc21.O=C1NCc2ccccc21 | [CH3;D1;+0:1]-[O;H0;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[#8:5]-[CH3;D1;+0:6].[C:7]-[#7:8]1-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c;H0;D3;+0:11]2:[c:12]:[c:13]:[c:14]:[c:15]:[c;H0;D3;+0:16]:2-[CH;D3;+0:17]-1-[OH;D1;+0:18].[C:19]-[#7:20]1-[C;H0;D3;+0:21](=[O;D1;H0:22])-[c;H0;D3;+0:23]2:[c:24]:[c:25]:[c:26]:[c:27]:[c;H0;D3;+0:2... | null | [] | 20 | CELSIUS | null | null | Ethyl (5-trifluoromethyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate and ethyl (6-trifluoromethyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate are prepared as described in Example 2, starting with 1.32 g of 60% sodium hydride in 120 cm3 of 1,2-dimethoxyethane, 6.57 cm3 of triethyl phosphonoacetate an... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amide.Tertiary amide.Secondary alcohol.Secondary alcohol | Ester.Ester.Tertiary amide.Tertiary amide | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | Other | null | 20 | null | CC(C)CN1C(=O)c2cc(C(F)(F)F)ccc2C1O.CC(C)CN1C(=O)c2ccc(C(F)(F)F)cc2C1O.COCCOC>>CCOC(=O)CC1c2cc(C(F)(F)F)ccc2C(=O)N1CC(C)C.CCOC(=O)CC1c2ccc(C(F)(F)F)cc2C(=O)N1CC(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-80a11acd650b4e7eab47616b569985b3 | CC(C)CN1C(=O)c2ccc(C(F)(F)F)cc2C1=O.O>>CC(C)CN1C(=O)c2cc(C(F)(F)F)ccc2C1O.CC(C)CN1C(=O)c2ccc(C(F)(F)F)cc2C1O | FC(C=1C=C2C(C(=O)N(C2=O)CC(C)C)=CC1)(F)F.O>>FC(C1=CC=C2C(N(C(C2=C1)=O)CC(C)C)O)(F)F.FC(C=1C=C2C(N(C(C2=CC1)=O)CC(C)C)O)(F)F | [CH3:1][CH:21]([CH2:4][N:5]1[C:25](=[O:26])[c:27]2[cH:28][cH:29][c:30]([C:31]([F:12])([F:14])[F:34])[cH:35][c:36]2[C:37]1=[O:38])[CH3:11].[OH2:7]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16][c:17]2[CH:18]1[OH:19].[CH3:20][CH:21]([CH3:22])[CH2:23][N:24]1... | CC(C)CN1C(=O)c2ccc(C(F)(F)F)cc2C1=O.O | CC(C)CN1C(=O)c2cc(C(F)(F)F)ccc2C1O.CC(C)CN1C(=O)c2ccc(C(F)(F)F)cc2C1O | null | null | [BH4-].[K+].CO | Aromatic Heterocycle Formation | OtherReaction | e4f3ae5275cd862e13f3273d210cd60a39d558600dc1a0f4901b083f858ac0c0 | b62fa8b67b6dea62f57ad0bc3864994c950d139694efad0b1d73e172fc7e0cf5 | O=C1NCc2ccccc21.O=C1NCc2ccccc21 | [CH3;D1;+0:1]-[CH;D3;+0:2](-[CH3;D1;+0:3])-[CH2;D2;+0:4]-[N;H0;D3;+0:5]1-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8]2:[c:9]:[c:10]:[c:11](-[C;H0;D4;+0:12](-[F;D1;H0:13])(-[F;H0;D1;+0:14])-[F;H0;D1;+0:15]):[c:16]:[c:17]:2-[C;H0;D3;+0:18]-1=[O;H0;D1;+0:19].[OH2;D0;+0:20]>>[C;D1;H3:21]-[CH;D3;+0:2](-[C;D1;H3:22])-[C:23]-[#7:24]1-[... | 160.8 | [{"value": 160.8, "product": "FC(C=1C=C2C(N(C(C2=CC1)=O)CC(C)C)O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 16 | HOUR | 5-Trifluoromethyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one and 6-trifluoromethyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one are prepared as described in Example 1, starting with 14.9 g of 4-trifluoromethyl-N-isobutylphthalimide in 300 cm3 of methanol and 2.96 g of potassium borohydride. The reaction mixture i... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Substituted dicarboximide | Trifluoro group.Trifluoro group.Tertiary amide.Tertiary amide.Secondary alcohol.Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | Other | [BH4-].[K+].CO | 20 | 16 | CC(C)CN1C(=O)c2ccc(C(F)(F)F)cc2C1=O.O>[BH4-].[K+].CO>CC(C)CN1C(=O)c2cc(C(F)(F)F)ccc2C1O.CC(C)CN1C(=O)c2ccc(C(F)(F)F)cc2C1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bc678ceaffb94426a0467a40e180f547 | CC(C)CN.O=C1OC(=O)c2cc(C(F)(F)F)ccc21>>CC(C)CN1C(=O)c2ccc(C(F)(F)F)cc2C1=O | FC(C=1C=C2C(C(=O)OC2=O)=CC1)(F)F.C(C(C)C)N.C1(=CC=C(C=C1)S(=O)(=O)O)C>>FC(C=1C=C2C(C(=O)N(C2=O)CC(C)C)=CC1)(F)F | [CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5].O1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][c:17]2[C:18]1=[O:19]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][c:17]2[C:18]1=[O:19] | CC(C)CN.O=C1OC(=O)c2cc(C(F)(F)F)ccc21 | CC(C)CN1C(=O)c2ccc(C(F)(F)F)cc2C1=O | null | null | C1(=CC=CC=C1)C | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[c:10](:[c:11]):[c:8](:[c:9])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | null | [] | 140 | CELSIUS | null | null | 4-Trifluoromethyl-N-isobutylphthalimide is prepared as described in Example 2, starting with 14.8 g of 4-trifluoromethylphthalic anhydride, 7.2 cm3 of isobutylamine and a catalytic amount of para-toluenesulfonic acid in 160 cm3 of toluene. The reaction mixture is heated at a temperature in the region of 140° C. for 5 h... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | C1(=CC=CC=C1)C | 140 | null | CC(C)CN.O=C1OC(=O)c2cc(C(F)(F)F)ccc21>C1(=CC=CC=C1)C>CC(C)CN1C(=O)c2ccc(C(F)(F)F)cc2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fa2e29fc363c4393b8c8453589380eb7 | CCOC(=O)CC1c2ccc(OC(C)C)cc2C(=O)N1CC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2cc(OC(C)C)ccc2C1CC(=O)NC(=N)N | [Na].[Cl-].NC(=[NH2+])N.C(C)(C)OC=1C=C2C(N(C(C2=CC1)CC(=O)OCC)CC(C)C)=O>>C(C(C)C)N1C(C2=CC=C(C=C2C1=O)OC(C)C)CC(=O)NC(=N)N | CCO[C:20]([CH2:19][CH:18]1[N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:6](=[O:7])[c:8]2[cH:9][c:10]([O:11][CH:12]([CH3:13])[CH3:14])[cH:15][cH:16][c:17]21)=[O:21].[NH2:22][C:23]([NH2:24])=[NH2+:25]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][c:10]([O:11][CH:12]([CH3:13])[CH3:14])[cH:15][cH:16][c:17]2[CH:18]... | CCOC(=O)CC1c2ccc(OC(C)C)cc2C(=O)N1CC(C)C.NC(N)=[NH2+] | CC(C)CN1C(=O)c2cc(OC(C)C)ccc2C1CC(=O)NC(=N)N | null | null | C(C)O | Acylation | OtherReaction | 2a0d0bb811d7d0d78ab0e0e0dd422aa0d95347cc6185304b02293baab0b54666 | bd0631f52f11765fc496c7945dc73cbc70f74ea4cf87d492a8fafb124a54fd13 | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[NH2+;D1:6]=[C;H0;D3;+0:7](-[NH2;D1;+0:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[NH2;D1;+0:6])=[NH;D1;+0:9] | 4 | [{"value": 4.0, "product": "C(C(C)C)N1C(C2=CC=C(C=C2C1=O)OC(C)C)CC(=O)NC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 18 | HOUR | N-[2-(2-Isobutyl-5-isopropoxy-3-oxo-2,3-dihydro-1H-isoindol-1-yl)-acetyl]-guanidine is prepared as described in Example 9, starting with 20 cm3 of absolute ethanol, 0.086 g of sodium, 0.36 g of guanidinium chloride and 0.42 g of ethyl (5-isopropyloxy-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate. The reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide.Primary amine | null | null | c1ccc2c(c1)C[NH]C2 | HO- | C(C)O | 20 | 18 | CCOC(=O)CC1c2ccc(OC(C)C)cc2C(=O)N1CC(C)C.NC(N)=[NH2+]>C(C)O>CC(C)CN1C(=O)c2cc(OC(C)C)ccc2C1CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3f6aa0b566a4969bcee0ee90c3ebf10 | CC(C)CN1C(=O)c2ccc(OC(C)C)cc2C1O.O>>CCOC(=O)CC1c2ccc(OC(C)C)cc2C(=O)N1CC(C)C | [H-].[Na+].C(C)(C)OC=1C=C2C(N(C(C2=CC1)=O)CC(C)C)O.O>>C(C)(C)OC=1C=C2C(N(C(C2=CC1)CC(=O)OCC)CC(C)C)=O | [CH3:1][CH:13]([O:12][c:11]1[cH:9][c:8]2[c:17]([cH:16][cH:10]1)[C:18](=[O:19])[N:20]([CH2:21][CH:22]([CH3:23])[CH3:24])[CH:7]2[OH:5])[CH3:15].[OH2:3]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[c:8]2[cH:9][cH:10][c:11]([O:12][CH:13]([CH3:14])[CH3:15])[cH:16][c:17]2[C:18](=[O:19])[N:20]1[CH2:21][CH:22]([CH3:23])[CH3... | CC(C)CN1C(=O)c2ccc(OC(C)C)cc2C1O.O | CCOC(=O)CC1c2ccc(OC(C)C)cc2C(=O)N1CC(C)C | null | null | COCCOC | Acylation | OtherReaction | 9431162f4b61d6285783d941b2fe083a1e97fbfe6db09639a37d68fe4088d6a7 | f9d6c48cce2371b8da82e921e7975e3937854c11baada232d9ed3e1d8c7bc0db | O=C1NCc2ccccc21 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]2:[cH;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[#8:9]-[CH;D3;+0:10](-[C;D1;H3:11])-[CH3;D1;+0:12]):[cH;D2;+0:13]:[c:14]:2-[CH;D3;+0:15]-1-[OH;D1;+0:16].[OH2;D0;+0:17]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]2:[cH;D2;+0:6]:[c;H0;D3;+0:8](-[#8:9]-[CH;D3;+0:10](-[C;D1;H3:18])-[C;D1;H3:1... | null | [] | 20 | CELSIUS | null | null | Ethyl (5-isopropyloxy-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate is prepared as described in Example 2, starting with 0.149 g of 60% sodium hydride in 20 cm3 of 1,2-dimethoxyethane, 1.23 cm3 of triethyl phosphonoacetate and 1.08 g of 5-isopropyloxy-3-hydroxy-2-isobutyl-2,3-dihydro-isoindol-1-one. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol | Ester.Ether | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | Other | COCCOC | 20 | null | CC(C)CN1C(=O)c2ccc(OC(C)C)cc2C1O.O>COCCOC>CCOC(=O)CC1c2ccc(OC(C)C)cc2C(=O)N1CC(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-07df97015a174e91b1461d8c8e727946 | CC(C)CN1C(=O)c2ccc(OC(C)C)cc2C1=O>>CC(C)CN1C(=O)c2ccc(OC(C)C)cc2C1O | C(C(C)C)N1C(C=2C(C1=O)=CC(=CC2)OC(C)C)=O.O>>C(C)(C)OC=1C=C2C(N(C(C2=CC1)=O)CC(C)C)O | [CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([O:12][CH:13]([CH3:14])[CH3:15])[cH:16][c:17]2[C:18]1=[O:19]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([O:12][CH:13]([CH3:14])[CH3:15])[cH:16][c:17]2[CH:18]1[OH:19] | CC(C)CN1C(=O)c2ccc(OC(C)C)cc2C1=O | CC(C)CN1C(=O)c2ccc(OC(C)C)cc2C1O | null | null | [BH4-].[K+].CO | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1NCc2ccccc21 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 92.4 | [{"value": 92.4, "product": "C(C)(C)OC=1C=C2C(N(C(C2=CC1)=O)CC(C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 17 | HOUR | 5-Isopropyloxy-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 1.16 g of N-isobutyl-4-isopropyloxyphthalimide in 20 cm3 of methanol and 0.24 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 17 hours and then cool... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | null | [BH4-].[K+].CO | 20 | 17 | CC(C)CN1C(=O)c2ccc(OC(C)C)cc2C1=O>[BH4-].[K+].CO>CC(C)CN1C(=O)c2ccc(OC(C)C)cc2C1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c5f237b2d7c84b948202dfeb7e36f388 | CC(C)Br.CC(C)CN1C(=O)c2ccc(O)cc2C1=O>>CC(C)CN1C(=O)c2ccc(OC(C)C)cc2C1=O | OC=1C=C2C(C(=O)N(C2=O)CC(C)C)=CC1.BrC(C)C.C([O-])([O-])=O.[K+].[K+]>>C(C(C)C)N1C(C=2C(C1=O)=CC(=CC2)OC(C)C)=O | Br[CH:13]([CH3:14])[CH3:15].[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:16][c:17]2[C:18]1=[O:19]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([O:12][CH:13]([CH3:14])[CH3:15])[cH:16][c:17]2[C:18]1=[O:19] | CC(C)Br.CC(C)CN1C(=O)c2ccc(O)cc2C1=O | CC(C)CN1C(=O)c2ccc(OC(C)C)cc2C1=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | bff4876be49b448135c783dd3eeeb68ab3cc5bdc91beadda8a9095106cd5c747 | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | O=C1NC(=O)c2ccccc21 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 60 | CELSIUS | 17 | HOUR | A mixture of 1 g of 4-hydroxy-N-isobutylphthalimide, 0.85 cm3 of 2-bromopropane and 1.38 g of potassium carbonate in 5 cm3 of dimethylformamide is stirred at a temperature in the region of 60° C. for 17 hours. The reaction mixture is then cooled to a temperature in the region of 20° C. and then concentrated to dryness ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)C[NH]C2 | HBr | CN(C=O)C | 60 | 17 | CC(C)Br.CC(C)CN1C(=O)c2ccc(O)cc2C1=O>CN(C=O)C>CC(C)CN1C(=O)c2ccc(OC(C)C)cc2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5e041bb17b184daa98c689fd6550a79d | CC(=O)Oc1ccc2c(c1)C(=O)OC2=O.CC(C)CN>>CC(C)CN1C(=O)c2ccc(O)cc2C1=O | C(C)(=O)OC=1C=C2C(C(=O)OC2=O)=CC1.C(C(C)C)N.C1(=CC=C(C=C1)S(=O)(=O)O)C>>OC=1C=C2C(C(=O)N(C2=O)CC(C)C)=CC1 | CC(=O)[O:12][c:11]1[cH:10][cH:9][c:8]2[c:14]([cH:13]1)[C:15](=[O:16])O[C:6]2=[O:7].[CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:13][c:14]2[C:15]1=[O:16] | CC(=O)Oc1ccc2c(c1)C(=O)OC2=O.CC(C)CN | CC(C)CN1C(=O)c2ccc(O)cc2C1=O | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 4426da7b9ff3850b4860c68f12842b4a9b5cd80f984597b746fbea93119ad9c5 | 3854c499f8bc211ab83cf60501e3c53dcb79f3dde4ccfc877f4cac8c198a4d9c | O=C1NC(=O)c2ccccc21 | C-C(=O)-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5]2:[c:6](:[c:7]:1)-[C;H0;D3;+0:8](=[O;D1;H0:9])-O-[C;H0;D3;+0:10]-2=[O;D1;H0:11].[C:12]-[C:13]-[NH2;D1;+0:14]>>[C:12]-[C:13]-[N;H0;D3;+0:14]1-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c:6]2:[c:7]:[c:2](-[OH;D1;+0:1]):[c:3]:[c:4]:[c:5]:2-[C;H0;D3;+0:10]-1=[O;D1;H0:11] | null | [] | 140 | CELSIUS | 1.5 | HOUR | 4-Hydroxy-N-isobutylphthalimide is prepared as described in Example 2, starting with 7.26 g of 4-acetoxyphthalic anhydride, 7.35 cm3 of isobutylamine and a catalytic amount of para-toluenesulfonic acid in 75 cm3 of toluene. The reaction mixture is heated at a temperature in the region of 140° C. for 4 hours and then co... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Ester.Primary amine | Substituted dicarboximide.Aromatic alcohol | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | C1(=CC=CC=C1)C | 140 | 1.5 | CC(=O)Oc1ccc2c(c1)C(=O)OC2=O.CC(C)CN>C1(=CC=CC=C1)C>CC(C)CN1C(=O)c2ccc(O)cc2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e00eddfb4ac249bf9f014dfcc2aeece2 | CCOC(=O)CC1c2c(F)cccc2C(=O)N1CC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2cccc(F)c2C1CC(=O)NC(=N)N | CC(C)([O-])C.[K+].[Cl-].NC(=[NH2+])N.FC=1C=CC=C2C(N(C(C12)CC(=O)OCC)CC(C)C)=O>>FC=1C=CC=C2C(N(C(C12)CC(=O)NC(=N)N)CC(C)C)=O | CCO[C:17]([CH2:16][CH:15]1[N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][c:12]([F:13])[c:14]21)=[O:18].[NH2:19][C:20]([NH2:21])=[NH2+:22]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][c:12]([F:13])[c:14]2[CH:15]1[CH2:16][C:17](=[O:18])[NH:19][C:20](=[NH:21])[NH... | CCOC(=O)CC1c2c(F)cccc2C(=O)N1CC(C)C.NC(N)=[NH2+] | CC(C)CN1C(=O)c2cccc(F)c2C1CC(=O)NC(=N)N | null | null | null | Acylation | OtherReaction | 2a0d0bb811d7d0d78ab0e0e0dd422aa0d95347cc6185304b02293baab0b54666 | bd0631f52f11765fc496c7945dc73cbc70f74ea4cf87d492a8fafb124a54fd13 | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[NH2+;D1:6]=[C;H0;D3;+0:7](-[NH2;D1;+0:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[NH2;D1;+0:6])=[NH;D1;+0:9] | 21.4 | [{"value": 21.4, "product": "FC=1C=CC=C2C(N(C(C12)CC(=O)NC(=N)N)CC(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | N-[(7-Fluoro-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 1, starting with 1.29 g of potassium tert-butoxide, 1.32 g of guanidinium chloride and 0.67 g of ethyl (7-fluoro-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate. The reaction mixture is stirred at a tem... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide.Primary amine | null | null | c1ccc2c(c1)C[NH]C2 | HO- | null | 20 | 20 | CCOC(=O)CC1c2c(F)cccc2C(=O)N1CC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2cccc(F)c2C1CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eca74393ec4e4c3fb8f3921e68fd6d01 | CC(C)CN1C(=O)c2cccc(F)c2C1=O>>CC(C)CN1C(=O)c2cccc(F)c2C1O | FC1=C2C(C(=O)N(C2=O)CC(C)C)=CC=C1>>FC1=C2C(N(C(C2=CC=C1)=O)CC(C)C)O | [CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][c:12]([F:13])[c:14]2[C:15]1=[O:16]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][c:12]([F:13])[c:14]2[CH:15]1[OH:16] | CC(C)CN1C(=O)c2cccc(F)c2C1=O | CC(C)CN1C(=O)c2cccc(F)c2C1O | null | null | [BH4-].[K+].CO | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1NCc2ccccc21 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 88.9 | [{"value": 88.9, "product": "FC1=C2C(N(C(C2=CC=C1)=O)CC(C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 19 | HOUR | 4-Fluoro-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1 starting with 3.9 g of 3-fluoro-N-isobutylphthalimide in 20 cm3 of methanol and 0.95 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 19 hours and is then cooled to a tem... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | null | [BH4-].[K+].CO | 20 | 19 | CC(C)CN1C(=O)c2cccc(F)c2C1=O>[BH4-].[K+].CO>CC(C)CN1C(=O)c2cccc(F)c2C1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cbdf2c15a68c4c8bbaa462ea6aa0317e | CC(C)CN.O=C1OC(=O)c2c(F)cccc21>>CC(C)CN1C(=O)c2cccc(F)c2C1=O | FC1=C2C(C(=O)OC2=O)=CC=C1.C(C(C)C)N.C1(=CC=C(C=C1)S(=O)(=O)O)C>>FC1=C2C(C(=O)N(C2=O)CC(C)C)=CC=C1 | [CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5].O1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][c:12]([F:13])[c:14]2[C:15]1=[O:16]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][c:12]([F:13])[c:14]2[C:15]1=[O:16] | CC(C)CN.O=C1OC(=O)c2c(F)cccc21 | CC(C)CN1C(=O)c2cccc(F)c2C1=O | null | null | C1(=CC=CC=C1)C | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[c:10](:[c:11]):[c:8](:[c:9])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | null | [] | 140 | CELSIUS | null | null | 3-Fluoro-N-isobutylphthalimide is prepared as described in Example 2, starting with 3.4 g of 3-fluorophthalic anhydride, 2.0 cm3 of isobutylamine and a catalytic amount of para-toluenesulfonic acid in 20 cm3 of toluene. The reaction mixture is heated at a temperature in the region of 140° C. for 3 hours. After cooling ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | C1(=CC=CC=C1)C | 140 | null | CC(C)CN.O=C1OC(=O)c2c(F)cccc21>C1(=CC=CC=C1)C>CC(C)CN1C(=O)c2cccc(F)c2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6d16386a67ab42f5b744701a9d4bc6d1 | CCOC(=O)CC1c2cc(Cl)c(Cl)cc2C(=O)N1CC(C)C>>CC(C)CN1C(=O)c2cc(Cl)c(Cl)cc2C1CC(=O)O | [Na].[Na].ClC=1C=C2C(N(C(C2=CC1Cl)CC(=O)OCC)CC(C)C)=O.[Cl-].NC(=[NH2+])N>>ClC=1C=C2C(N(C(C2=CC1Cl)CC(=O)O)CC(C)C)=O | CC[O:20][C:18]([CH2:17][CH:16]1[N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:6](=[O:7])[c:8]2[cH:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14][c:15]21)=[O:19]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14][c:15]2[CH:16]1[CH2:17][C:18](=[O:19])[OH:20] | CCOC(=O)CC1c2cc(Cl)c(Cl)cc2C(=O)N1CC(C)C | CC(C)CN1C(=O)c2cc(Cl)c(Cl)cc2C1CC(=O)O | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1NCc2ccccc21 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 42.1 | [{"value": 42.1, "product": "ClC=1C=C2C(N(C(C2=CC1Cl)CC(=O)O)CC(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 1.5 | HOUR | 0.09 g of sodium is added to 5 cm3 of absolute ethanol under an inert atmosphere. After the sodium has totally disappeared, 0.04 g of guanidinium chloride is added. The reaction mixture is stirred under an inert atmosphere at a temperature in the region of 20° C. for 1.5 hours, followed by addition of a solution of 0.9... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)C[NH]C2 | Other | C(C)O | 20 | 1.5 | CCOC(=O)CC1c2cc(Cl)c(Cl)cc2C(=O)N1CC(C)C>C(C)O>CC(C)CN1C(=O)c2cc(Cl)c(Cl)cc2C1CC(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9390d1324720489caf2104fa47e0587a | CC(C)CN1C(=O)c2cc(Cl)c(Cl)cc2C1O.CCOCC>>CCOC(=O)CC1c2cc(Cl)c(Cl)cc2C(=O)N1CC(C)C | C(C)OCC.[H-].[Na+].ClC=1C=C2C(N(C(C2=CC1Cl)=O)CC(C)C)O.O>>ClC=1C=C2C(N(C(C2=CC1Cl)CC(=O)OCC)CC(C)C)=O | [OH:5][CH:7]1[c:8]2[cH:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14][c:15]2[C:16](=[O:17])[N:18]1[CH2:19][CH:20]([CH3:21])[CH3:22].[CH3:1][CH2:2][O:3][CH2:4][CH3:6]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[c:8]2[cH:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14][c:15]2[C:16](=[O:17])[N:18]1[CH2:19][CH:20]([CH3:21])[CH3:22] | CC(C)CN1C(=O)c2cc(Cl)c(Cl)cc2C1O.CCOCC | CCOC(=O)CC1c2cc(Cl)c(Cl)cc2C(=O)N1CC(C)C | null | null | COCCOC | Heteroatom Alkylation and Arylation | OtherReaction | 48a0bd460ac260e177ffa262698d9e6ae802769dd91076aaf638df24b5a534e1 | 79b1dc52d3be254effebd4b18222e0510623f9682e37c200296c41f37c9f0926 | O=C1NCc2ccccc21 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9].[C:10]-[#8:11]-[CH2;D2;+0:12]-[CH3;D1;+0:13]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[CH2;D2;+0:13]-[C;H0;D3;+0:12](=[O;H0;D1;+0:9])-[#8:11]-[C:10] | null | [] | 20 | CELSIUS | null | null | Ethyl (5,6-dichloro-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate is prepared as described in Example 2, starting with 0.75 g of 60% sodium hydride in 45 cm3 of 1,2-dimethoxyethane, 3.71 cm3 of triethyl phosphonoacetate and 3.42 g of 5,6-dichloro-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one. The mixture is re... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol | Ester | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | null | COCCOC | 20 | null | CC(C)CN1C(=O)c2cc(Cl)c(Cl)cc2C1O.CCOCC>COCCOC>CCOC(=O)CC1c2cc(Cl)c(Cl)cc2C(=O)N1CC(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-688d8d59ac9d4758847774241978eef8 | CC(C)CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O>>CC(C)CN1C(=O)c2cc(Cl)c(Cl)cc2C1O | ClC=1C=C2C(C(=O)N(C2=O)CC(C)C)=CC1Cl>>ClC=1C=C2C(N(C(C2=CC1Cl)=O)CC(C)C)O | [CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14][c:15]2[C:16]1=[O:17]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][c:10]([Cl:11])[c:12]([Cl:13])[cH:14][c:15]2[CH:16]1[OH:17] | CC(C)CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O | CC(C)CN1C(=O)c2cc(Cl)c(Cl)cc2C1O | null | null | [BH4-].[K+].CO | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1NCc2ccccc21 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 89.8 | [{"value": 89.8, "product": "ClC=1C=C2C(N(C(C2=CC1Cl)=O)CC(C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 16 | HOUR | 5,6-Dichloro-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 3.78 g of 4,5-dichloro-N-isobutylphthalimide in 75 cm3 of methanol and 0.75 g of potassium borohydride. The reaction mixture is stirred at a temperature in the region of 20° C. for 16 hours and is then coole... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | null | [BH4-].[K+].CO | 20 | 16 | CC(C)CN1C(=O)c2cc(Cl)c(Cl)cc2C1=O>[BH4-].[K+].CO>CC(C)CN1C(=O)c2cc(Cl)c(Cl)cc2C1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc7455381f9940a5aca8ac46fe9bacd5 | CCOC(=O)CC1c2c(F)ccc(F)c2C(=O)N1CC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2c(F)ccc(F)c2C1CC(=O)NC(=N)N | FC1=C2C(N(C(C2=C(C=C1)F)CC(=O)OCC)CC(C)C)=O.CC(C)([O-])C.[K+].[Cl-].NC(=[NH2+])N>>FC1=C2C(N(C(C2=C(C=C1)F)CC(=O)NC(=N)N)CC(C)C)=O | CCO[C:18]([CH2:17][CH:16]1[N:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[C:6](=[O:7])[c:8]2[c:9]([F:10])[cH:11][cH:12][c:13]([F:14])[c:15]21)=[O:19].[NH2:20][C:21]([NH2:22])=[NH2+:23]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[c:9]([F:10])[cH:11][cH:12][c:13]([F:14])[c:15]2[CH:16]1[CH2:17][C:18](=[O:19])[NH:20][C:21... | CCOC(=O)CC1c2c(F)ccc(F)c2C(=O)N1CC(C)C.NC(N)=[NH2+] | CC(C)CN1C(=O)c2c(F)ccc(F)c2C1CC(=O)NC(=N)N | null | null | null | Acylation | OtherReaction | 2a0d0bb811d7d0d78ab0e0e0dd422aa0d95347cc6185304b02293baab0b54666 | bd0631f52f11765fc496c7945dc73cbc70f74ea4cf87d492a8fafb124a54fd13 | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[NH2+;D1:6]=[C;H0;D3;+0:7](-[NH2;D1;+0:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[NH2;D1;+0:6])=[NH;D1;+0:9] | null | [] | 20 | CELSIUS | 20 | HOUR | N-[(4,7-Difluoro-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 1, starting with 2.68 g of potassium tert-butoxide, 2.74 g of guanidinium chloride and 1.49 g of ethyl (4,7-difluoro-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate. The reaction mixture is stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide.Primary amine | null | null | c1ccc2c(c1)C[NH]C2 | HO- | null | 20 | 20 | CCOC(=O)CC1c2c(F)ccc(F)c2C(=O)N1CC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2c(F)ccc(F)c2C1CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a79682152cf846e7b8e90f252d3d262e | CC(C)CN1C(=O)c2c(F)ccc(F)c2C1=O>>CC(C)CN1C(=O)c2c(F)ccc(F)c2C1O | FC1=C2C(C(=O)N(C2=O)CC(C)C)=C(C=C1)F.O>>FC1=C2C(N(C(C2=C(C=C1)F)=O)CC(C)C)O | [CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[c:9]([F:10])[cH:11][cH:12][c:13]([F:14])[c:15]2[C:16]1=[O:17]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[c:9]([F:10])[cH:11][cH:12][c:13]([F:14])[c:15]2[CH:16]1[OH:17] | CC(C)CN1C(=O)c2c(F)ccc(F)c2C1=O | CC(C)CN1C(=O)c2c(F)ccc(F)c2C1O | null | null | [BH4-].[K+].CO | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1NCc2ccccc21 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 87.9 | [{"value": 87.9, "product": "FC1=C2C(N(C(C2=C(C=C1)F)=O)CC(C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 3 | HOUR | 4,7-Difluoro-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one is prepared as described in Example 1, starting with 6.41 g of 3,6-difluoro-N-isobutylphthalimide in 70 cm3 of methanol and 1.44 g of potassium borohydride. The reaction mixture is: stirred at a temperature in the region of 20° C. for 3 hours and is then coole... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | null | [BH4-].[K+].CO | 20 | 3 | CC(C)CN1C(=O)c2c(F)ccc(F)c2C1=O>[BH4-].[K+].CO>CC(C)CN1C(=O)c2c(F)ccc(F)c2C1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f52fc0d1191e4205b49c3b05602ca96c | CC(C)CN.O=C1OC(=O)c2c(F)ccc(F)c21>>CC(C)CN1C(=O)c2c(F)ccc(F)c2C1=O | FC1=C2C(C(=O)OC2=O)=C(C=C1)F.C(C(C)C)N.C1(=CC=C(C=C1)S(=O)(=O)O)C>>FC1=C2C(C(=O)N(C2=O)CC(C)C)=C(C=C1)F | [CH3:1][CH:2]([CH3:3])[CH2:4][NH2:5].O1[C:6](=[O:7])[c:8]2[c:9]([F:10])[cH:11][cH:12][c:13]([F:14])[c:15]2[C:16]1=[O:17]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[c:9]([F:10])[cH:11][cH:12][c:13]([F:14])[c:15]2[C:16]1=[O:17] | CC(C)CN.O=C1OC(=O)c2c(F)ccc(F)c21 | CC(C)CN1C(=O)c2c(F)ccc(F)c2C1=O | null | null | C1(=CC=CC=C1)C | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[c:10](:[c:11]):[c:8](:[c:9])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | null | [] | 20 | CELSIUS | null | null | 3,6-Difluoro-N-isobutylphthalimide is prepared as described in Example 2, starting with 5.0 g of 3,6-difluorophthalic anhydride, 2.7 cm3 of isobutylamine and a catalytic amount of para-toluenesulfonic acid in 50 cm3 of toluene. The reaction mixture is refluxed for 3 hours. After cooling to a temperature in the region o... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | C1(=CC=CC=C1)C | 20 | null | CC(C)CN.O=C1OC(=O)c2c(F)ccc(F)c21>C1(=CC=CC=C1)C>CC(C)CN1C(=O)c2c(F)ccc(F)c2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-61eb84261ad642118fa00b49b9d4e4a9 | CCOC(=O)CC1c2cccc(C)c2C(=O)N1CC(C)C.NC(N)=[NH2+]>>Cc1cccc2c1C(=O)N(CC(C)C)C2CC(=O)NC(=N)N | CC(C)([O-])C.[K+].[Cl-].NC(=[NH2+])N.CC1=C2C(N(C(C2=CC=C1)CC(=O)OCC)CC(C)C)=O>>C(C(C)C)N1C(C2=CC=CC(=C2C1=O)C)CC(=O)NC(=N)N | CCO[C:17]([CH2:16][CH:15]1[c:6]2[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:7]2[C:8](=[O:9])[N:10]1[CH2:11][CH:12]([CH3:13])[CH3:14])=[O:18].[NH2:19][C:20]([NH2:21])=[NH2+:22]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[C:8](=[O:9])[N:10]([CH2:11][CH:12]([CH3:13])[CH3:14])[CH:15]2[CH2:16][C:17](=[O:18])[NH:19][C:20](=[NH:21])[... | CCOC(=O)CC1c2cccc(C)c2C(=O)N1CC(C)C.NC(N)=[NH2+] | Cc1cccc2c1C(=O)N(CC(C)C)C2CC(=O)NC(=N)N | null | null | O | Acylation | OtherReaction | 2a0d0bb811d7d0d78ab0e0e0dd422aa0d95347cc6185304b02293baab0b54666 | bd0631f52f11765fc496c7945dc73cbc70f74ea4cf87d492a8fafb124a54fd13 | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[NH2+;D1:6]=[C;H0;D3;+0:7](-[NH2;D1;+0:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[NH2;D1;+0:6])=[NH;D1;+0:9] | 55.8 | [{"value": 55.8, "product": "C(C(C)C)N1C(C2=CC=CC(=C2C1=O)C)CC(=O)NC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 20 | HOUR | N-[2-(2-Isobutyl-4-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)-acetyl]-guanidine is prepared as described in Example 1, starting with 0.68 of potassium tert-butoxide, 0.58 g of guanidinium chloride and 0.36 g of ethyl (4-methyl-2-isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate. The reaction mixture is stirred at a t... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide.Primary amine | null | null | c1ccc2c(c1)C[NH]C2 | HO- | O | 20 | 20 | CCOC(=O)CC1c2cccc(C)c2C(=O)N1CC(C)C.NC(N)=[NH2+]>O>Cc1cccc2c1C(=O)N(CC(C)C)C2CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2c8eea89a8d4460bbbfab07745eb889a | Cc1cccc2c1C(=O)N(CC(C)C)C2=O.O>>Cc1cccc2c1C(=O)N(CC(C)C)C2O.Cc1cccc2c1C(O)N(CC(C)C)C2=O | C(C(C)C)N1C(C=2C(C1=O)=C(C=CC2)C)=O.O>>CC=1C=CC=C2C(N(C(C12)=O)CC(C)C)O.CC1=C2C(N(C(C2=CC=C1)=O)CC(C)C)O | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[C:8](=[O:9])[N:10]([CH2:11][CH:12]([CH3:13])[CH3:18])[C:15]2=[O:32].[OH2:16]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]1[C:8](=[O:9])[N:10]([CH2:11][CH:12]([CH3:13])[CH3:14])[CH:15]2[OH:16].[CH3:17][c:18]1[cH:19][cH:20][cH:21][c:22]2[c:23]1[CH:24]([OH:25])[N:26]([CH2:27][CH:... | Cc1cccc2c1C(=O)N(CC(C)C)C2=O.O | Cc1cccc2c1C(=O)N(CC(C)C)C2O.Cc1cccc2c1C(O)N(CC(C)C)C2=O | null | null | [BH4-].[K+].CO | Aromatic Heterocycle Formation | OtherReaction | 80e81150c5344eb5948e5ffa5d451e70555c1fccb2813d6b936dafb1decbe38f | 635345e99333bb5633c1a982d8704d75548f9c7be11489a084be362ff1b669ae | O=C1NCc2ccccc21.O=C1NCc2ccccc21 | [C;D1;H3:1]-[CH;D3;+0:2](-[CH3;D1;+0:3])-[C:4]-[#7:5]1-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](:[c:10])-[C;H0;D3;+0:11]-1=[O;H0;D1;+0:12].[OH2;D0;+0:13]>>[C;D1;H3:1]-[CH;D3;+0:2](-[C;D1;H3:14])-[C:4]-[#7:5]1-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](:[c:10])-[CH;D3;+0:11]-1-[OH;D1;+0:13].[C;D1;H3:15]-[c;H0;D3;+0:3](:[c:16]:[c:17]):[c:18... | null | [] | 20 | CELSIUS | 65 | HOUR | 4-Methyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one and 7-methyl-3-hydroxy-2-isobutyl-2,3-dihydroisoindol-1-one are prepared as described in Example 1, starting with 5.4 g of N-isobutyl-3-methylphthalimide in 20 cm3 of methanol and 1.4 g of potassium borohydride. The reaction mixture is stirred at a temperature in ... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Tertiary amide.Secondary alcohol.Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | Other | [BH4-].[K+].CO | 20 | 65 | Cc1cccc2c1C(=O)N(CC(C)C)C2=O.O>[BH4-].[K+].CO>Cc1cccc2c1C(=O)N(CC(C)C)C2O.Cc1cccc2c1C(O)N(CC(C)C)C2=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-820aabc2f56042d9a7389117d47630dc | NCC(F)(F)F.O=C1OC(=O)c2cc(C(F)(F)F)ccc21>>O=C1c2ccc(C(F)(F)F)cc2C(=O)N1CC(F)(F)F | FC(C=1C=C2C(OC(C2=CC1)=O)=O)(F)F.FC(CN)(F)F>>FC(CN1C(C2=CC=C(C=C2C1=O)C(F)(F)F)=O)(F)F | [NH2:15][CH2:16][C:17]([F:18])([F:19])[F:20].O1[C:2](=[O:1])[c:3]2[cH:4][cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][c:12]2[C:13]1=[O:14]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][c:12]2[C:13](=[O:14])[N:15]1[CH2:16][C:17]([F:18])([F:19])[F:20] | NCC(F)(F)F.O=C1OC(=O)c2cc(C(F)(F)F)ccc21 | O=C1c2ccc(C(F)(F)F)cc2C(=O)N1CC(F)(F)F | null | C1(=CC=C(C=C1)S(=O)(=O)O)C | CC(OCC)=O | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1NC(=O)c2ccccc21 | [F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[F;D1;H0:1]-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[c:13](:[c:14]):[c:11](:[c:12])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | 80 | [{"value": 80.0, "product": "FC(CN1C(C2=CC=C(C=C2C1=O)C(F)(F)F)=O)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 5.0 g of 5-trifluoromethyl-isobenzofuran-1,3-dione were dissolved using 50 ml of toluene(anhydrous) and 4.6 g of 2,2,2-trifluoro-ethylamine added. The mixture was left at ambient temperature for 16 h. 50 mg of toluene-4-sulfonic acid were then added and the mixture was refluxed for 5 h. 200 ml of EA were added and the ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | C1(=CC=C(C=C1)S(=O)(=O)O)C.CC(OCC)=O | null | 16 | NCC(F)(F)F.O=C1OC(=O)c2cc(C(F)(F)F)ccc21>C1(=CC=C(C=C1)S(=O)(=O)O)C.CC(OCC)=O>O=C1c2ccc(C(F)(F)F)cc2C(=O)N1CC(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-23a394f5306546038bf275f24874feae | O=C(O)c1ccc(C(F)(F)F)cc1C(=O)O>>O=C1OC(=O)c2cc(C(F)(F)F)ccc21 | FC(C=1C=C(C(C(=O)O)=CC1)C(=O)O)(F)F.C(C)(=O)OC(C)=O>>FC(C=1C=C2C(OC(C2=CC1)=O)=O)(F)F | O[C:2](=[O:1])[c:15]1[c:6]([C:4]([OH:3])=[O:5])[cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]1>>[O:1]=[C:2]1[O:3][C:4](=[O:5])[c:6]2[cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]21 | O=C(O)c1ccc(C(F)(F)F)cc1C(=O)O | O=C1OC(=O)c2cc(C(F)(F)F)ccc21 | null | null | CC(=O)O | Miscellaneous | OtherReaction | f6c3b96e71f2dd62de4cd2f6ba0ee0d42dced7c72ed20a339ce5512c7fff8e4d | 22fb50577915472f1babb105381e408122dc09b3472eabb73e6e4daecfef90f6 | O=C1OC(=O)c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[O;H0;D2;+0:8]-[C:6](=[O;D1;H0:7])-[c:5]:[c:3]-1:[c:4] | null | [] | null | null | null | null | 25.0 g of 4-trifluoromethyl-phthalic acid were dissolved in 50 ml of HOAc and 15.1 ml of acetic anhydride added. The mixture was refluxed for 6 h. The solvent was then removed in vacuo. The residue was treated three times with 50 ml of toluene each followed by the removal of the solvent in vacuo. Yield 23.1 g of a colo... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid | Anhydride | null | c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2 | HO- | CC(=O)O | null | null | O=C(O)c1ccc(C(F)(F)F)cc1C(=O)O>CC(=O)O>O=C1OC(=O)c2cc(C(F)(F)F)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b3fcc1e7440b4a269d9af8201ea07c7b | O=C(O)c1ccc(Cl)cc1C(=O)NCCC(F)(F)F>>O=C1c2ccc(Cl)cc2C(=O)N1CCC(F)(F)F | ClC=1C=C(C(C(=O)O)=CC1)C(=O)NCCC(F)(F)F.C1(=CC=C(C=C1)S(=O)(=O)O)C>>ClC=1C=C2C(C(=O)N(C2=O)CCC(F)(F)F)=CC1 | O[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([Cl:7])[cH:8][c:9]1[C:10](=[O:11])[NH:12][CH2:13][CH2:14][C:15]([F:16])([F:17])[F:18]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][c:6]([Cl:7])[cH:8][c:9]2[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][C:15]([F:16])([F:17])[F:18] | O=C(O)c1ccc(Cl)cc1C(=O)NCCC(F)(F)F | O=C1c2ccc(Cl)cc2C(=O)N1CCC(F)(F)F | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | d7fbb0259b6b0f12e2c885b7412dd93beb3544caef7818f594854d3230028a3d | 48e6b2b999f3f15ec39998545386900040317bcbdbb4347c7e2886995a8c9772 | O=C1NC(=O)c2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:10]-[C:9]-[N;H0;D3;+0:8]1-[C:6](=[O;D1;H0:7])-[c:5]:[c:3](:[c:4])-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | 89.5 | [{"value": 89.5, "product": "ClC=1C=C2C(C(=O)N(C2=O)CCC(F)(F)F)=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | A mixture of 5.0 g of 4-chloro-N-(3,3,3-trifluoropropyl)phthalamic acid and 30 mg of para-toluenesulfonic acid in 100 cm3 of toluene is refluxed with stirring for 7 hours. The reaction mixture is then concentrated to dryness under reduced pressure. 4.2 g of 4-chloro-N-(3,3,3-trifluoropropyl)phthalimide are thus obtaine... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amide | Substituted dicarboximide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | C1(=CC=CC=C1)C | null | 7 | O=C(O)c1ccc(Cl)cc1C(=O)NCCC(F)(F)F>C1(=CC=CC=C1)C>O=C1c2ccc(Cl)cc2C(=O)N1CCC(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3fec2dd936f14d04bb58f9128fe4bd66 | FC(F)(F)CCI.O=C1NC(=O)c2cc(Cl)ccc21>>O=C(O)c1ccc(Cl)cc1C(=O)NCCC(F)(F)F | Cl.FC(CCI)(F)F.ClC=1C=C2C(C(=O)NC2=O)=CC1.C([O-])([O-])=O.[K+].[K+]>>ClC=1C=C(C(C(=O)O)=CC1)C(=O)NCCC(F)(F)F | I[CH2:14][CH2:15][C:16]([F:17])([F:18])[F:19].[O:1]=[C:2]1[c:4]2[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]2[C:11](=[O:12])[NH:13]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][c:10]1[C:11](=[O:12])[NH:13][CH2:14][CH2:15][C:16]([F:17])([F:18])[F:19] | FC(F)(F)CCI.O=C1NC(=O)c2cc(Cl)ccc21 | O=C(O)c1ccc(Cl)cc1C(=O)NCCC(F)(F)F | null | null | O.CN(C=O)C | Acylation | OtherReaction | d630c9baaf27a4550b2c2822f6f52caf76cae5da2ce55bafe9665fa3f6a17b02 | 9891512d75b55e457603aea4ae9bd9289966bb585bb045450013b8407ea1727c | c1ccccc1 | I-[CH2;D2;+0:1]-[C:2]-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6].[O;D1;H0:7]=[C:8]1-[NH;D2;+0:9]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[c:12](:[c:13]):[c:14]-1>>[F;D1;H0:4]-[C:3](-[F;D1;H0:5])(-[F;D1;H0:6])-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:9]-[C:8](=[O;D1;H0:7])-[c:14]:[c:12](-[C;H0;D3;+0:10](=[O;D1;H0:11])-[O;D1;H1:15]):[c:1... | 105.2 | [{"value": 105.2, "product": "ClC=1C=C(C(C(=O)O)=CC1)C(=O)NCCC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | null | null | 3.6 g of 1,1,1-trifluoro-3-iodopropane are added dropwise to a mixture of 7.5 g of 4-chlorophthalimide and 4.6 g of potassium carbonate in 40 cm3 of dimethylformamide at a temperature in the region of 110° C. with stirring. After stirring for 11 hours at a temperature in the region of 120° C., the reaction mixture is c... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Unsubstituted dicarboximide | Carboxylic acid.Secondary amide | c1ccc2c(c1)CNC2 | null | c1ccccc1 | null | O.CN(C=O)C | 20 | null | FC(F)(F)CCI.O=C1NC(=O)c2cc(Cl)ccc21>O.CN(C=O)C>O=C(O)c1ccc(Cl)cc1C(=O)NCCC(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a119c77f3fcb488fb7c2f4d718a10521 | NC=O.O=C1OC(=O)c2cc(Cl)ccc21>>O=C1NC(=O)c2cc(Cl)ccc21 | ClC=1C=C2C(C(=O)OC2=O)=CC1.C(=O)N.O>>ClC=1C=C2C(C(=O)NC2=O)=CC1 | O=C[NH2:3].O1[C:2](=[O:1])[c:12]2[c:6]([cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[C:4]1=[O:5]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[cH:7][c:8]([Cl:9])[cH:10][cH:11][c:12]21 | NC=O.O=C1OC(=O)c2cc(Cl)ccc21 | O=C1NC(=O)c2cc(Cl)ccc21 | null | null | null | Acylation | OtherReaction | 1b08e306e982a756f62b8091da5c6965e8ab805fb2f38ac4d4c370ba372f11cb | b1548f80df3f5850960252a7f6b180e1b02eb1ec59e1c45c5494f5aa39e38642 | O=C1NC(=O)c2ccccc21 | O=C-[NH2;D1;+0:1].[O;D1;H0:2]=[C;H0;D3;+0:3]1-O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8]-1:[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:3]1-[NH;D2;+0:1]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8]-1:[c:9] | 104.6 | [{"value": 104.6, "product": "ClC=1C=C2C(C(=O)NC2=O)=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 3 | HOUR | A solution of 10.0 g of 4-chlorophthalic anhydride in 24.6 g of formamide is heated at a temperature in the region of 120° C. with stirring for 3 hours and is then cooled to a temperature in the region of 20° C. and poured into 100 cm3 of water. After stirring for 30 minutes, the mixture is filtered and the precipitate... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amide | Unsubstituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)CNC2 | c1ccc2c(c1)CNC2 | HO- | null | 20 | 3 | NC=O.O=C1OC(=O)c2cc(Cl)ccc21>>O=C1NC(=O)c2cc(Cl)ccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-13d23906f9bf4fdab40d38eebd64d16c | CCCN.CCOC(=O)C(C)=Cc1ccccc1C(=O)O>>CCCNC(=O)c1ccccc1C=C(C)C(=O)OCC | C(CC)N.C(C)N(CC)CC.F[B-](F)(F)F.C(#N)C(C(=O)OCC)=NOC(=[N+](C)C)N(C)C.C(C)OC(=O)C(=CC1=C(C(=O)O)C=CC=C1)C.C(C)N(CC)CC>>CC(C(=O)OCC)=CC1=C(C=CC=C1)C(NCCC)=O | [CH3:1][CH2:2][CH2:3][NH2:4].O[C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[CH:13]=[C:14]([CH3:15])[C:16](=[O:17])[O:18][CH2:19][CH3:20]>>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[CH:13]=[C:14]([CH3:15])[C:16](=[O:17])[O:18][CH2:19][CH3:20] | CCCN.CCOC(=O)C(C)=Cc1ccccc1C(=O)O | CCCNC(=O)c1ccccc1C=C(C)C(=O)OCC | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[C:6]=[C:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:7]=[C:6]-[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9]-[C:8]):[c:4] | 79.9 | [{"value": 79.9, "product": "CC(C(=O)OCC)=CC1=C(C=CC=C1)C(NCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | A solution of 0.69 cm3 (5.0 mmol) of triethylamine and 1.64 g (5.0 mmol) of O-[(cyano(ethoxycarbonyl)methylene)amino]-1,1,3,3-tetramethyluronium tetrafluoroborate (“TOTU”) in 6 cm3 of dimethylformamide is added at 0° C. to a solution of 1.17 g (5.0 mmol) of 2-(2-ethoxycarbonylpropen-1-yl)benzoic acid in 10 cm3 of dimet... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | CN(C=O)C | 0 | 0.5 | CCCN.CCOC(=O)C(C)=Cc1ccccc1C(=O)O>CN(C=O)C>CCCNC(=O)c1ccccc1C=C(C)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6b8a37e00587416cad369e3624f6633b | CCOC(=O)C(C)=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccccc1C(=O)O>>CCOC(=O)C(C)=Cc1ccccc1C(=O)O | C(=O)C1=C(C(=O)O)C=CC=C1.C1(=CC=CC=C1)P(=C(C(=O)OCC)C)(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)OC(=O)C(=CC1=C(C(=O)O)C=CC=C1)C | c1ccc(P(c2ccccc2)(c2ccccc2)=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7])cc1.O=[CH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[C:15](=[O:16])[OH:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])=[CH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[C:15](=[O:16])[OH:17] | CCOC(=O)C(C)=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccccc1C(=O)O | CCOC(=O)C(C)=Cc1ccccc1C(=O)O | null | null | CN(C=O)C | C-C Coupling | Wittig reaction with triphenylphosphorane | 71bd2654cede51545adee465eb47bf49794d5c57afe21c7fb122478c5a700139 | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7].[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C;H0;D3;+0:12](-[C;D1;H3:13])=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C;H0;D3;+0:12](-[C;D1;H3:13])=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[O;D1;H1:7] | null | [] | 20 | CELSIUS | 1 | HOUR | A mixture of 5.0 g (33.3 mmol) of 2-formylbenzoic acid and 14.5 g (40.0 mmol) of ethyl 2-(triphenylphosphanylidene)propionate in 100 cm3 of dimethylformamide is stirred at a temperature in the region of 20° C. for 1 hour. After removal of the solvent, the residue is dissolved in dichloromethane and then extracted twice... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | CN(C=O)C | 20 | 1 | CCOC(=O)C(C)=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccccc1C(=O)O>CN(C=O)C>CCOC(=O)C(C)=Cc1ccccc1C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f35e3b4b3d3c485d9652df08ba3abb70 | CCCCNC(=O)c1ccccc1C=C(C)C(=O)OCC.NC(N)=[NH2+]>>CCCCN1C(=O)c2ccccc2C1C(C)C(=O)NC(=N)N | C(CCC)NC(=O)C1=C(C=CC=C1)C=C(C(=O)OCC)C.[Cl-].NC(=[NH2+])N.CC(C)([O-])C.[K+]>>C(CCC)N1C(C2=CC=CC=C2C1=O)C(C(=O)NC(=N)N)C | CCO[C:17]([C:15](=[CH:14][c:13]1[c:8]([C:6]([NH:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:7])[cH:9][cH:10][cH:11][cH:12]1)[CH3:16])=[O:18].[NH2:19][C:20]([NH2:21])=[NH2+:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH:14]1[CH:15]([CH3:16])[C:17](=[O:18])[NH:19][C:20](=[NH:21])[N... | CCCCNC(=O)c1ccccc1C=C(C)C(=O)OCC.NC(N)=[NH2+] | CCCCN1C(=O)c2ccccc2C1C(C)C(=O)NC(=N)N | null | null | CN(C=O)C | Acylation | OtherReaction | dcf49378e6619ff85ba9e749476a6064de1ac232fdca8843859076840b880ae5 | bfdf9d8794c4f418c67cbf27cf7a81922d1c4e071347e361c5160485b9471d6e | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-[C;D1;H3:4])=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]-[C:9](=[O;D1;H0:10])-[NH;D2;+0:11]-[C:12]-[C:13].[NH2+;D1:14]=[C;H0;D3;+0:15](-[NH2;D1;+0:16])-[NH2;D1;+0:17]>>[C:13]-[C:12]-[N;H0;D3;+0:11]1-[C:9](=[O;D1;H0:10])-[c:8]:[c:6](:[c:7])-[CH;D3;+0:5]-1-[CH;D3;+0:3](-[C;D1;H3:4]... | 93.1 | [{"value": 93.1, "product": "C(CCC)N1C(C2=CC=CC=C2C1=O)C(C(=O)NC(=N)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 45 | MINUTE | N-[2-(2-Butyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionyl]guanidine is prepared as described in Example 30, starting with 3.63 g (38.0 mmol) of guanidinium chloride in 20 cm3 of dimethylformamide and 3.84 g (34.2 mmol) of potassium tert-butoxide. The mixture is stirred for 45 minutes at a temperature in the region of ... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester.Secondary amide | Secondary amide.Tertiary amide.Primary amine | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | CN(C=O)C | 20 | 0.75 | CCCCNC(=O)c1ccccc1C=C(C)C(=O)OCC.NC(N)=[NH2+]>CN(C=O)C>CCCCN1C(=O)c2ccccc2C1C(C)C(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a9829b5a2b6d4b1e89b997d8209c3e25 | CCCCN.CCOC(=O)C(C)=Cc1ccccc1C(=O)O>>CCCCNC(=O)c1ccccc1C=C(C)C(=O)OCC | C(C)OC(=O)C(=CC1=C(C(=O)O)C=CC=C1)C.C(C)N(CC)CC.F[B-](F)(F)F.C(#N)C(C(=O)OCC)=NOC(=[N+](C)C)N(C)C.C(CCC)N.C(C)N(CC)CC>>C(CCC)NC(=O)C1=C(C=CC=C1)C=C(C(=O)OCC)C | [CH3:1][CH2:2][CH2:3][CH2:4][NH2:5].O[C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[CH:14]=[C:15]([CH3:16])[C:17](=[O:18])[O:19][CH2:20][CH3:21]>>[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[CH:14]=[C:15]([CH3:16])[C:17](=[O:18])[O:19][CH2:20][CH3:21] | CCCCN.CCOC(=O)C(C)=Cc1ccccc1C(=O)O | CCCCNC(=O)c1ccccc1C=C(C)C(=O)OCC | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[C:6]=[C:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:7]=[C:6]-[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9]-[C:8]):[c:4] | 78.1 | [{"value": 78.1, "product": "C(CCC)NC(=O)C1=C(C=CC=C1)C=C(C(=O)OCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl 3-(2-butylcarbamoylphenyl)-2-methylacrylate is prepared as described in Example 30, starting with 1.17 g (5.0 mmol) of 2-(2-ethoxycarbonylpropen-1-yl)benzoic acid in 10 cm3 of dimethylformamide, a solution of 0.69 cm3 (5.0 mmol) of triethylamine, 1.64 g (5.0 mmol) of O-[(cyano(ethoxycarbonyl)methylene)amino]-1,1,... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | CN(C=O)C | null | null | CCCCN.CCOC(=O)C(C)=Cc1ccccc1C(=O)O>CN(C=O)C>CCCCNC(=O)c1ccccc1C=C(C)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e9998e321b44409ca8f8cc9686415b43 | CCOC(=O)C(C)=Cc1ccccc1C(=O)NCC(C)C.NC(N)=[NH2+]>>CC(C)CN1C(=O)c2ccccc2C1C(C)C(=O)NC(=N)N | C(C(C)C)NC(=O)C1=C(C=CC=C1)C=C(C(=O)OCC)C.[Cl-].NC(=[NH2+])N.CC(C)([O-])C.[K+]>>C(C(C)C)N1C(C2=CC=CC=C2C1=O)C(C(=O)NC(=N)N)C | CCO[C:17]([C:15](=[CH:14][c:13]1[c:8]([C:6]([NH:5][CH2:4][CH:2]([CH3:1])[CH3:3])=[O:7])[cH:9][cH:10][cH:11][cH:12]1)[CH3:16])=[O:18].[NH2:19][C:20]([NH2:21])=[NH2+:22]>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[CH:14]1[CH:15]([CH3:16])[C:17](=[O:18])[NH:19][C:20](=[NH:21])... | CCOC(=O)C(C)=Cc1ccccc1C(=O)NCC(C)C.NC(N)=[NH2+] | CC(C)CN1C(=O)c2ccccc2C1C(C)C(=O)NC(=N)N | null | null | CN(C=O)C | Acylation | OtherReaction | dcf49378e6619ff85ba9e749476a6064de1ac232fdca8843859076840b880ae5 | bfdf9d8794c4f418c67cbf27cf7a81922d1c4e071347e361c5160485b9471d6e | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-[C;D1;H3:4])=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]-[C:9](=[O;D1;H0:10])-[NH;D2;+0:11]-[C:12]-[C:13].[NH2+;D1:14]=[C;H0;D3;+0:15](-[NH2;D1;+0:16])-[NH2;D1;+0:17]>>[C:13]-[C:12]-[N;H0;D3;+0:11]1-[C:9](=[O;D1;H0:10])-[c:8]:[c:6](:[c:7])-[CH;D3;+0:5]-1-[CH;D3;+0:3](-[C;D1;H3:4]... | 73.1 | [{"value": 73.1, "product": "C(C(C)C)N1C(C2=CC=CC=C2C1=O)C(C(=O)NC(=N)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 45 | MINUTE | N-[2-(2-Isobutyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)propionyl]guanidine is prepared as described in Example 30, starting with 3.73 g (39.0 mmol) of guanidinium chloride in 20 cm3 of dimethylformamide and 3.94 g (35.1 mmol) of potassium tert-butoxide. The mixture is stirred for 45 minutes at a temperature in the region ... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester.Secondary amide | Secondary amide.Tertiary amide.Primary amine | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | CN(C=O)C | 20 | 0.75 | CCOC(=O)C(C)=Cc1ccccc1C(=O)NCC(C)C.NC(N)=[NH2+]>CN(C=O)C>CC(C)CN1C(=O)c2ccccc2C1C(C)C(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4367c72295bc4b1ba1276fa164677eda | CC(C)CN.CCOC(=O)C(C)=Cc1ccccc1C(=O)O>>CCOC(=O)C(C)=Cc1ccccc1C(=O)NCC(C)C | C(C)OC(=O)C(=CC1=C(C(=O)O)C=CC=C1)C.C(C)N(CC)CC.F[B-](F)(F)F.C(#N)C(C(=O)OCC)=NOC(=[N+](C)C)N(C)C.C(C(C)C)N.C(C)N(CC)CC>>C(C(C)C)NC(=O)C1=C(C=CC=C1)C=C(C(=O)OCC)C | [NH2:17][CH2:18][CH:19]([CH3:20])[CH3:21].O[C:15]([c:14]1[c:9]([CH:8]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7])[cH:10][cH:11][cH:12][cH:13]1)=[O:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])=[CH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[C:15](=[O:16])[NH:17][CH2:18][CH:19]([CH3:20])[CH3:21] | CC(C)CN.CCOC(=O)C(C)=Cc1ccccc1C(=O)O | CCOC(=O)C(C)=Cc1ccccc1C(=O)NCC(C)C | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[C:6]=[C:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[C:6]=[C:7] | 79.5 | [{"value": 79.5, "product": "C(C(C)C)NC(=O)C1=C(C=CC=C1)C=C(C(=O)OCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ethyl 3-(2-isobutylcarbamoylphenyl)-2-methylacrylate is prepared as described in Example 30, starting with 1.17 g (5.0 mmol) of 2-(2-ethoxycarbonylpropen-1-yl)benzoic acid in 10 cm3 of dimethylformamide, a solution of 0.69 cm3 (5.0 mmol) of triethylamine, 1.64 g (5.0 mmol) of O-[(cyano(ethoxycarbonyl)methylene)amino]-1... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | CN(C=O)C | null | null | CC(C)CN.CCOC(=O)C(C)=Cc1ccccc1C(=O)O>CN(C=O)C>CCOC(=O)C(C)=Cc1ccccc1C(=O)NCC(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a4fe38235e304d6b9283db789fffcca0 | CCOC(=O)C(C)=Cc1ccccc1C(=O)O.NCCO>>CCOC(=O)C(C)=Cc1ccccc1C(=O)NCCO | C(O)CN.C(C)N(CC)CC.F[B-](F)(F)F.C(#N)C(C(=O)OCC)=NOC(=[N+](C)C)N(C)C.C(C)N(CC)CC.C(C)OC(=O)C(=CC1=C(C(=O)O)C=CC=C1)C>>OCCNC(=O)C1=C(C=CC=C1)C=C(C(=O)OCC)C | O[C:15]([c:14]1[c:9]([CH:8]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7])[cH:10][cH:11][cH:12][cH:13]1)=[O:16].[NH2:17][CH2:18][CH2:19][OH:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])=[CH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[C:15](=[O:16])[NH:17][CH2:18][CH2:19][OH:20] | CCOC(=O)C(C)=Cc1ccccc1C(=O)O.NCCO | CCOC(=O)C(C)=Cc1ccccc1C(=O)NCCO | null | null | CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[C:6]=[C:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[C:6]=[C:7] | null | [] | null | null | null | null | Ethyl 3-[2-(2-hydroxyethylcarbamoyl)phenyl]-2-methylacrylate is prepared as described in Example 30, starting with 1.17 g (5.0 mmol) of 2-(2-ethoxycarbonylpropen-1-yl)benzoic acid in 10 cm3 of dimethylformamide, a solution of 0.69 cm3 (5.0 mmol) of triethylamine and 1.64 g (5.0 mmol) of O-[(cyano(ethoxycarbonyl)methyle... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | CN(C=O)C | null | null | CCOC(=O)C(C)=Cc1ccccc1C(=O)O.NCCO>CN(C=O)C>CCOC(=O)C(C)=Cc1ccccc1C(=O)NCCO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b94f6d23a63143b8aab50c54215d1082 | CCOC(=O)CC1c2ccc(C)cc2C(=O)N1CC(C)C.NC(N)=[NH2+]>>Cc1ccc2c(c1)C(=O)N(CC(C)C)C2CC(=O)NC(=N)N | CC(C)([O-])C.[K+].[Cl-].NC(=[NH2+])N.C(C(C)C)N1C(C2=CC=C(C=C2C1=O)C)CC(=O)OCC>>C(C(C)C)N1C(C2=CC=C(C=C2C1=O)C)CC(=O)NC(=N)N | CCO[C:17]([CH2:16][CH:15]1[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:7][c:6]2[C:8](=[O:9])[N:10]1[CH2:11][CH:12]([CH3:13])[CH3:14])=[O:18].[NH2:19][C:20]([NH2:21])=[NH2+:22]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[N:10]([CH2:11][CH:12]([CH3:13])[CH3:14])[CH:15]2[CH2:16][C:17](=[O:18])[NH:19][C:20](=[NH:21]... | CCOC(=O)CC1c2ccc(C)cc2C(=O)N1CC(C)C.NC(N)=[NH2+] | Cc1ccc2c(c1)C(=O)N(CC(C)C)C2CC(=O)NC(=N)N | null | null | O | Acylation | OtherReaction | 2a0d0bb811d7d0d78ab0e0e0dd422aa0d95347cc6185304b02293baab0b54666 | bd0631f52f11765fc496c7945dc73cbc70f74ea4cf87d492a8fafb124a54fd13 | O=C1NCc2ccccc21 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5].[NH2+;D1:6]=[C;H0;D3;+0:7](-[NH2;D1;+0:8])-[NH2;D1;+0:9]>>[#7:5]-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C;H0;D3;+0:7](-[NH2;D1;+0:6])=[NH;D1;+0:9] | 70.2 | [{"value": 70.2, "product": "C(C(C)C)N1C(C2=CC=C(C=C2C1=O)C)CC(=O)NC(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 40 | HOUR | N-[(2-Isobutyl-5-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 1, starting with 1.75 g of potassium tert-butoxide, 1.78 g of guanidinium chloride and 0.9 g of ethyl (2-isobutyl-5-methyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetate. The reaction mixture is stirred at a temp... | 10.6084/m9.figshare.5104873.v1 | null | Amidinium.Amidinium.Ester | Secondary amide.Primary amine | null | null | c1ccc2c(c1)C[NH]C2 | HO- | O | 20 | 40 | CCOC(=O)CC1c2ccc(C)cc2C(=O)N1CC(C)C.NC(N)=[NH2+]>O>Cc1ccc2c(c1)C(=O)N(CC(C)C)C2CC(=O)NC(=N)N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7818423844994ab0963b37067607d149 | Cc1ccc2c(c1)C(=O)N(CC(C)C)C2=O.O>>Cc1ccc2c(c1)C(=O)N(CC(C)C)C2O.Cc1ccc2c(c1)C(O)N(CC(C)C)C2=O | O.C(C(C)C)N1C(C=2C(C1=O)=CC(=CC2)C)=O>>OC1N(C(C2=CC=C(C=C12)C)=O)CC(C)C.OC1N(C(C2=CC(=CC=C12)C)=O)CC(C)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[N:10]([CH2:11][CH:12]([CH3:13])[CH3:18])[C:15]2=[O:16].[OH2:25]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[N:10]([CH2:11][CH:12]([CH3:13])[CH3:14])[CH:15]2[OH:16].[CH3:17][c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23]1)[CH:24]([OH:25])[N:26]([CH2:2... | Cc1ccc2c(c1)C(=O)N(CC(C)C)C2=O.O | Cc1ccc2c(c1)C(=O)N(CC(C)C)C2O.Cc1ccc2c(c1)C(O)N(CC(C)C)C2=O | null | null | [BH4-].[K+].CO | Aromatic Heterocycle Formation | OtherReaction | 80e81150c5344eb5948e5ffa5d451e70555c1fccb2813d6b936dafb1decbe38f | 635345e99333bb5633c1a982d8704d75548f9c7be11489a084be362ff1b669ae | O=C1NCc2ccccc21.O=C1NCc2ccccc21 | [C;D1;H3:1]-[CH;D3;+0:2](-[CH3;D1;+0:3])-[C:4]-[#7:5]1-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](:[c:10])-[C;H0;D3;+0:11]-1=[O;H0;D1;+0:12].[OH2;D0;+0:13]>>[#7:14]-[C:15](-[OH;D1;+0:13])-[c:16]:[c:17]:[c;H0;D3;+0:3](-[C;D1;H3:18]):[c:19]:[c:20].[C;D1;H3:1]-[CH;D3;+0:2](-[C;D1;H3:21])-[C:4]-[#7:5]1-[C:6](=[O;D1;H0:7])-[c:8]:[c:9]... | null | [] | 20 | CELSIUS | 16 | HOUR | 3-Hydroxy-2-isobutyl-5-methyl-2,3-dihydroisoindol-1-one and 3-hydroxy-2-isobutyl-6-methyl-2,3-dihydroisoindol-1-one are prepared as described in Example 1, starting with 6.7 g of N-isobutyl-4-methylphthalimide in 65 cm3 of methanol and 1.7 g of potassium borohydride. The reaction mixture is stirred at a temperature in ... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Tertiary amide.Secondary alcohol.Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.c1ccc2c(c1)C[NH]C2 | Other | [BH4-].[K+].CO | 20 | 16 | Cc1ccc2c(c1)C(=O)N(CC(C)C)C2=O.O>[BH4-].[K+].CO>Cc1ccc2c(c1)C(=O)N(CC(C)C)C2O.Cc1ccc2c(c1)C(O)N(CC(C)C)C2=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8d0acc1108a0435e9315b9e987106bc9 | CC(C)CN.Cc1ccc2c(c1)C(=O)OC2=O>>Cc1ccc2c(c1)C(=O)N(CC(C)C)C2=O | CC=1C=C2C(C(=O)OC2=O)=CC1.C(C(C)C)N.C1(=CC=C(C=C1)S(=O)(=O)O)C>>C(C(C)C)N1C(C=2C(C1=O)=CC(=CC2)C)=O | [NH2:10][CH2:11][CH:12]([CH3:13])[CH3:14].O1[C:8](=[O:9])[c:6]2[c:5]([cH:4][cH:3][c:2]([CH3:1])[cH:7]2)[C:15]1=[O:16]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[N:10]([CH2:11][CH:12]([CH3:13])[CH3:14])[C:15]2=[O:16] | CC(C)CN.Cc1ccc2c(c1)C(=O)OC2=O | Cc1ccc2c(c1)C(=O)N(CC(C)C)C2=O | null | null | C1(=CC=CC=C1)C | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1NC(=O)c2ccccc21 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[c:10](:[c:11]):[c:8](:[c:9])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | null | [] | 140 | CELSIUS | null | null | N-Isobutyl-4-methylphthalimide is prepared as described in Example 2, starting with 6.0 g of 4-methylphthalic anhydride, 3.7 cm3 of isobutylamine and a catalytic amount of para-toluenesulphonic acid in 60 cm3 of toluene. The reaction mixture is heated at a temperature in the region of 140° C. for three hours and is the... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | C1(=CC=CC=C1)C | 140 | null | CC(C)CN.Cc1ccc2c(c1)C(=O)OC2=O>C1(=CC=CC=C1)C>Cc1ccc2c(c1)C(=O)N(CC(C)C)C2=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a67c2ef8ada640688782f3602f512067 | CCOC(=O)CP(=O)(OCC)OCC.CS(=O)(=O)c1ccc2c(c1)C(O)N(CC(F)(F)F)C2=O>>CCOC(=O)CC1c2cc(S(C)(=O)=O)ccc2C(=O)N1CC(F)(F)F | [H-].[Na+].OC1N(C(C2=CC=C(C=C12)S(=O)(=O)C)=O)CC(F)(F)F.CC(OCC)=O.C(C)OC(CP(=O)(OCC)OCC)=O>>C(C)OC(CC1N(C(C2=CC=C(C=C12)S(=O)(=O)C)=O)CC(F)(F)F)=O | CCOP(=O)(OCC)[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].O[CH:7]1[c:8]2[cH:9][c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15][cH:16][c:17]2[C:18](=[O:19])[N:20]1[CH2:21][C:22]([F:23])([F:24])[F:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[c:8]2[cH:9][c:10]([S:11]([CH3:12])(=[O:13])=[O:14])[cH:15][cH:16][c:17]2[C:18](... | CCOC(=O)CP(=O)(OCC)OCC.CS(=O)(=O)c1ccc2c(c1)C(O)N(CC(F)(F)F)C2=O | CCOC(=O)CC1c2cc(S(C)(=O)=O)ccc2C(=O)N1CC(F)(F)F | null | null | COCCOC | C-C Coupling | OtherReaction | f15997e17baabc84ad1f24d90439ac1e1bf9c091e3c8b61c6d23db78bb59ba96 | ec740fdba0adc3c659d56447beb3ee7a35d222db2ebbeacae7f761e1e85567b3 | O=C1NCc2ccccc21 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].O-[CH;D3;+0:6]1-[#7:7](-[C:8])-[C:9](=[O;D1;H0:10])-[c:11]:[c:12]-1:[c:13]>>[C:8]-[#7:7]1-[C:9](=[O;D1;H0:10])-[c:11]:[c:12](:[c:13])-[CH;D3;+0:6]-1-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5] | null | [] | null | null | 1 | HOUR | 0.56 g of a 60% suspension of NaH in mineral oil were suspended in 20 ml of DME. Afterwards, 2.8 ml of (diethoxy-phosphoryl)-acetic acid ethyl ester were added dropwise at ambient temperature and the mixture stirred for 1 h at that temperature. A solution prepared of 3-hydroxy-5-methanesulfonyl-2-(2,2,2-trifluoro-ethyl... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol | Ester | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HO- | COCCOC | null | 1 | CCOC(=O)CP(=O)(OCC)OCC.CS(=O)(=O)c1ccc2c(c1)C(O)N(CC(F)(F)F)C2=O>COCCOC>CCOC(=O)CC1c2cc(S(C)(=O)=O)ccc2C(=O)N1CC(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5390950b57c245ada9df498f35e40b07 | CS(=O)(=O)c1ccc2c(c1)C(=O)N(CC(F)(F)F)C2=O>>CS(=O)(=O)c1ccc2c(c1)C(O)N(CC(F)(F)F)C2=O | CS(=O)(=O)C=1C=C2C(N(C(C2=CC1)=O)CC(F)(F)F)=O.CO>>OC1N(C(C2=CC=C(C=C12)S(=O)(=O)C)=O)CC(F)(F)F | [CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11](=[O:12])[N:13]([CH2:14][C:15]([F:16])([F:17])[F:18])[C:19]2=[O:20]>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[CH:11]([OH:12])[N:13]([CH2:14][C:15]([F:16])([F:17])[F:18])[C:19]2=[O:20] | CS(=O)(=O)c1ccc2c(c1)C(=O)N(CC(F)(F)F)C2=O | CS(=O)(=O)c1ccc2c(c1)C(O)N(CC(F)(F)F)C2=O | null | null | O | Reduction | OtherReaction | e8ffc87e9d14ec555652bcd3de186a7602297c1d65bf6096cdb1ce7e169ed644 | 6c2222fa5333790df8c936ae3761255cb080c6e237292637f62137781815b926 | O=C1NCc2ccccc21 | [C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[C;H0;D3;+0:8]-1=[O;H0;D1;+0:9]>>[C:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](:[c:7])-[CH;D3;+0:8]-1-[OH;D1;+0:9] | 40.9 | [{"value": 40.9, "product": "OC1N(C(C2=CC=C(C=C12)S(=O)(=O)C)=O)CC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | 3.4 g of 5-methanesulfonyl-2-(2,2,2-trifluoro-ethyl)-isoindole-1,3-dione were dissolved using 240 ml of MeOH. 0.63 g of KBH4 were then added in small portions at ambient temperature. The reaction mixture was stirred for 20 h at ambient temperature and subsequently poured into 1 l of water at 0° C. The aqueous layer was... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Secondary alcohol | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | null | O | null | 20 | CS(=O)(=O)c1ccc2c(c1)C(=O)N(CC(F)(F)F)C2=O>O>CS(=O)(=O)c1ccc2c(c1)C(O)N(CC(F)(F)F)C2=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b1499d818a0a41168cce09489ab320a9 | CCOC(=O)CC1c2cc(C(F)(F)F)ccc2C(=O)N1CC1CC1>>O=C(O)CC1c2cc(C(F)(F)F)ccc2C(=O)N1CC1CC1 | C(C)OC(CC1N(C(C2=CC=C(C=C12)C(F)(F)F)=O)CC1CC1)=O.[OH-].[Na+]>>C1(CC1)CN1C(C2=CC(=CC=C2C1=O)C(F)(F)F)CC(=O)O | CC[O:3][C:2](=[O:1])[CH2:4][CH:5]1[c:6]2[cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]2[C:16](=[O:17])[N:18]1[CH2:19][CH:20]1[CH2:21][CH2:22]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH:5]1[c:6]2[cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14][c:15]2[C:16](=[O:17])[N:18]1[CH2:19][CH:20]1[CH2:21][CH2:22]1 | CCOC(=O)CC1c2cc(C(F)(F)F)ccc2C(=O)N1CC1CC1 | O=C(O)CC1c2cc(C(F)(F)F)ccc2C(=O)N1CC1CC1 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1c2ccccc2CN1CC1CC1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 38.1 | [{"value": 38.1, "product": "C1(CC1)CN1C(C2=CC(=CC=C2C1=O)C(F)(F)F)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 1.0 g of (2-cyclopropylmethyl-3-oxo-6-trifluoromethyl-2,3-dihydro-1H-isoindol-1-yl)acetic acid ethyl ester were dissolved using 10 ml of ethanol and 3.5 ml of a 1 N aqueous solution of NaOH added. The mixture was stirred for 3 h at ambient temperature and then the solvent removed in vacuo. Afterwards, 30 ml of water we... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2c(c1)C[NH]C2.C1CC1 | Other | C(C)O | null | 3 | CCOC(=O)CC1c2cc(C(F)(F)F)ccc2C(=O)N1CC1CC1>C(C)O>O=C(O)CC1c2cc(C(F)(F)F)ccc2C(=O)N1CC1CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-49d1b00280dc4566a34df497dbc0ccdf | COc1cc(C=CC(=O)c2cc(OC)c(OC)c(OC)c2)cc(Br)c1OC.OB(O)c1cccs1>>COc1cc(C(=O)C=Cc2cc(OC)c(OC)c(-c3cccs3)c2)cc(OC)c1OC | O.S1C(=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+].BrC=1C=C(C=C(C1OC)OC)C=CC(=O)C1=CC(=C(C(=C1)OC)OC)OC>>COC=1C=C(C=C(C1OC)C=1SC=CC1)C=CC(=O)C1=CC(=C(C(=C1)OC)OC)OC | Br[c:26]1[cH:25][c:5]([CH:6]=[CH:8][C:9](=[O:7])[c:10]2[cH:11][c:12]([O:13][CH3:14])[c:15]([O:16][CH3:17])[c:18]([O:27][CH3:28])[cH:24]2)[cH:4][c:3]([O:2][CH3:1])[c:29]1[O:30][CH3:31].OB(O)[c:19]1[cH:20][cH:21][cH:22][s:23]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH:8]=[CH:9][c:10]2[cH:11][c:12]([O:13][CH3:14])[c... | COc1cc(C=CC(=O)c2cc(OC)c(OC)c(OC)c2)cc(Br)c1OC.OB(O)c1cccs1 | COc1cc(C(=O)C=Cc2cc(OC)c(OC)c(-c3cccs3)c2)cc(OC)c1OC | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC | C-C Coupling | Suzuki coupling with boronic acids | b91b99e20230b8ee23ff9c0be751d7e6e9088c9bf2e3c3634cb219f57c76935c | 3574f5ee80f247e8e9144c7409a97dc71fd4c3d1727016fd405b163a1bb17c74 | O=C(C=Cc1cccc(-c2cccs2)c1)c1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[CH;D2;+0:4]=[CH;D2;+0:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c:8]2:[c:9]:[c:10]:[c:11](-[#8:12]):[c;H0;D3;+0:13](-[O;H0;D2;+0:14]-[C;D1;H3:15]):[c:16]:2):[c:17]:[c:18]:[c:19]:1-[#8:20].O-B(-O)-[c;H0;D3;+0:21]1:[#16;a:22]:[c:23]:[c:24]:[c:25]:1>>[#8:12]-[c:11]1:[c:10]:[c:9]:[c:8](-[CH;D2;+0... | 90 | [{"value": 90.0, "product": "COC=1C=C(C=C(C1OC)C=1SC=CC1)C=CC(=O)C1=CC(=C(C(=C1)OC)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.7, "product": "COC=1C=C(C=C(C1OC)C=1SC=CC1)C=CC(=O)C1=CC(=C(C(=C1)OC)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | 3-(3-Bromo-4,5-dimethoxyphenyl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one (0.105 g, 0.2 mmol) from Ex-1A was dissolved in ethylene glycol dimethyl ether (20 mL). Tetrakis(triphenylphosphine)palladium(0) (0.116 g, 0.1 mmol) was added, and the mixture was stirred at room temperature under nitrogen for 5 min. 2-Thiopheneb... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ether.Boronic acid | Ketone.Ether | c1ccccc1.c1ccccc1.c1ccsc1 | c1ccccc1.c1ccccc1.c1ccsc1 | c1ccccc1.c1ccccc1.c1ccsc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC | null | 0.083333 | COc1cc(C=CC(=O)c2cc(OC)c(OC)c(OC)c2)cc(Br)c1OC.OB(O)c1cccs1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC>COc1cc(C(=O)C=Cc2cc(OC)c(OC)c(-c3cccs3)c2)cc(OC)c1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-099c434db9f545c5b23d9e1b226a3eb0 | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cc2ccccc2s1>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O | O.S1C2=C(C=C1B(O)O)C=CC=C2.C([O-])([O-])=O.[Na+].[Na+].BrC=1C(=CC(=C(C=O)C1)OC)OC>>S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)OC)OC)C=CC=C2 | Br[c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:19]([CH:20]=[O:21])[cH:18]1.OB(O)[c:9]1[cH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[s:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[s:17]2)[cH:18][c:19]1[CH:20]=[O:21] | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cc2ccccc2s1 | COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC | C-C Coupling | Suzuki coupling with boronic acids | a1259a94b31ac9f1988cb839e0910c5b2437b7522341904299ff46277eacea87 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3ccccc3s2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1):[c:2]:[c:3]-[C:4]=[O;D1;H0:5] | 83 | [{"value": 83.0, "product": "S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)OC)OC)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.6, "product": "S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)OC)OC)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | Ex-6A: 5-Bromo-2,4-dimethoxybenzaldehyde (4.9 g, 20.0 mmol) was dissolved in ethylene glycol dimethyl ether (50 mL). Tetrakis(triphenylphosphine)palladium(0) (2.32 g, 2 mmol) was added, and the mixture was stirred at room temperature under nitrogen for 5 min. Benzo[b]thiophene-2-boronic acid (4.27 g, 24 mmol) and sodiu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2sccc2c1 | c1ccccc1.c1ccc2sccc2c1 | c1ccccc1.c1ccc2sccc2c1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC | null | 0.083333 | COc1cc(OC)c(C=O)cc1Br.OB(O)c1cc2ccccc2s1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC>COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-98b804334ce24a75927b047571b456ff | COc1cc(C(C)=O)cc(OC)c1OC.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=CC(=O)c1cc(OC)c(OC)c(OC)c1 | COC=1C=C(C=C(C1OC)OC)C(C)=O.[OH-].[Na+].S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)OC)OC)C=CC=C2>>S1C2=C(C=C1C=1C(=CC(=C(C1)C=CC(=O)C1=CC(=C(C(=C1)OC)OC)OC)OC)OC)C=CC=C2 | [CH3:21][C:22](=[O:23])[c:24]1[cH:25][c:26]([O:27][CH3:28])[c:29]([O:30][CH3:31])[c:32]([O:33][CH3:34])[cH:35]1.O=[CH:20][c:19]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[s:17]2)[cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11... | COc1cc(C(C)=O)cc(OC)c1OC.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O | COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=CC(=O)c1cc(OC)c(OC)c(OC)c1 | null | null | C(C)O | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(C=Cc1cccc(-c2cc3ccccc3s2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])-[CH;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 92 | [{"value": 92.0, "product": "S1C2=C(C=C1C=1C(=CC(=C(C1)C=CC(=O)C1=CC(=C(C(=C1)OC)OC)OC)OC)OC)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.0, "product": "S1C2=C(C=C1C=1C(=CC(=C(C1)C=CC(=O)C1=CC(=C(C(=C1)OC)OC)OC)OC)OC)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 3′,4′,5′-Trimethoxyacetophenone (1.62 g, 7.7 mmol) was dissolved in ethanol (50 mL). Sodium hydroxide solution (50%, 4 mL) was added and the mixture was stirred at room temperature for 30 minutes. 5-(Benzo[b]thien-2-yl)-2,4-dimethoxybenzaldehyde (2.2 g, 7.7 mmol) from Ex-6A was added, and the mixture was stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccc2sccc2c1.c1ccccc1 | HO- | C(C)O | null | 0.5 | COc1cc(C(C)=O)cc(OC)c1OC.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O>C(C)O>COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=CC(=O)c1cc(OC)c(OC)c(OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-754c7a9dc18444ce999681af4bf22fa9 | COc1cc(I)ccc1C(C)=O.OB(O)c1cccs1>>COc1cc(-c2cccs2)ccc1C(C)=O | O.S1C(=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+].IC1=CC(=C(C=C1)C(C)=O)OC>>COC1=C(C=CC(=C1)C=1SC=CC1)C(C)=O | I[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:13]([C:14]([CH3:15])=[O:16])[cH:12][cH:11]1.OB(O)[c:6]1[cH:7][cH:8][cH:9][s:10]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][s:10]2)[cH:11][cH:12][c:13]1[C:14]([CH3:15])=[O:16] | COc1cc(I)ccc1C(C)=O.OB(O)c1cccs1 | COc1cc(-c2cccs2)ccc1C(C)=O | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC | C-C Coupling | Suzuki coupling with boronic acids | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccs2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[c:10]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6]1:[#16;a:7]:[c:8]:[c:9]:[c:10]:1):[c:4]:[c:5] | 98 | [{"value": 98.0, "product": "COC1=C(C=CC(=C1)C=1SC=CC1)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.1, "product": "COC1=C(C=CC(=C1)C=1SC=CC1)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-57a: 4′-iodo-2′-methoxyacetophenone (1.08 g, 3.9 mmol) in ethylene glycol dimethyl ether (50 ml) was degassed for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.456 g, 0.39 mmol), thiophene-2-boronic acid (0.75 g, 5.9 mmol), and sodium carbonate solution (2 m, 4 ml, 8 mmol) were added. The mixture was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | HI.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC | null | null | COc1cc(I)ccc1C(C)=O.OB(O)c1cccs1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC>COc1cc(-c2cccs2)ccc1C(C)=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-080b4e4ea4564d1bb6cac95e8adafada | COc1cc(-c2cccs2)ccc1C(C)=O.O=Cc1ccc(F)c(F)c1>>COc1cc(-c2cccs2)ccc1C(=O)C=Cc1ccc(F)c(F)c1 | COC1=C(C=CC(=C1)C=1SC=CC1)C(C)=O.FC=1C=C(C=O)C=CC1F.C([O-])([O-])=O.[Cs+].[Cs+]>>FC=1C=C(C=CC1F)C=CC(=O)C1=C(C=C(C=C1)C=1SC=CC1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][s:10]2)[cH:11][cH:12][c:13]1[C:14](=[O:15])[CH3:16].O=[CH:17][c:18]1[cH:19][cH:20][c:21]([F:22])[c:23]([F:24])[cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][s:10]2)[cH:11][cH:12][c:13]1[C:14](=[O:15])[CH:16]=[CH:17][c:18]1[cH:19][cH:20][c:21]([F... | COc1cc(-c2cccs2)ccc1C(C)=O.O=Cc1ccc(F)c(F)c1 | COc1cc(-c2cccs2)ccc1C(=O)C=Cc1ccc(F)c(F)c1 | null | null | O1CCCC1 | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(C=Cc1ccccc1)c1ccc(-c2cccs2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])-[CH;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 69.1 | [{"value": 69.0, "product": "FC=1C=C(C=CC1F)C=CC(=O)C1=C(C=C(C=C1)C=1SC=CC1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.1, "product": "FC=1C=C(C=CC1F)C=CC(=O)C1=C(C=C(C=C1)C=1SC=CC1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The 2′-methoxy-4′-(thien-2-yl)acetophenone (0.30 g, 1.3 mmol) from Ex-57A and 3,4-difluorobenzaldehyde 0.19 g, 1.3 mmol) were mixed in tetrahydrofuran (THF, 10 mL). Cesium carbonate (1.2 g, 3.9 mmol) was added, and the mixture was stirred at reflux overnight. Upon cooling to room temperature, the mixture was filtered, ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | HO- | O1CCCC1 | null | null | COc1cc(-c2cccs2)ccc1C(C)=O.O=Cc1ccc(F)c(F)c1>O1CCCC1>COc1cc(-c2cccs2)ccc1C(=O)C=Cc1ccc(F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2095895f6d47499b941b0e13f624eeae | CC(C)(C)[Si](C)(C)Cl.COc1cc(C(C)=O)cc(OC)c1O>>COc1cc(C(C)=O)cc(OC)c1O[Si](C)(C)C(C)(C)C | OC1=C(C=C(C=C1OC)C(C)=O)OC.[Si](C)(C)(C(C)(C)C)Cl.N1C=NC=C1>>COC=1C=C(C=C(C1O[Si](C)(C)C(C)(C)C)OC)C(C)=O | Cl[Si:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[CH3:21].[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][c:10]([O:11][CH3:12])[c:13]1[OH:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][c:10]([O:11][CH3:12])[c:13]1[O:14][Si:15]([CH3:16])([CH3:17])[C:18]([CH3:19])([CH3:20])[CH3:21] | CC(C)(C)[Si](C)(C)Cl.COc1cc(C(C)=O)cc(OC)c1O | COc1cc(C(C)=O)cc(OC)c1O[Si](C)(C)C(C)(C)C | null | null | CN(C=O)C | Protection | Alcohol protection with silyl ethers | 91043baed1393f1ecd2302d7d0b31c01cf171d3977dd7c70afa1da52fa298c73 | 4a917c959d011f885a1269fa3c1f022ee5e09144996246d24e42e65634a451ac | c1ccccc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3])(-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | 81 | [{"value": 81.0, "product": "COC=1C=C(C=C(C1O[Si](C)(C)C(C)(C)C)OC)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.8, "product": "COC=1C=C(C=C(C1O[Si](C)(C)C(C)(C)C)OC)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Ex-59A: To a solution of 4′-hydroxy-3′,5′-dimethoxyacetophenone (1 g, 5.1 mmol) in N,N-dimethylformamide were added tert-butyldimethylsilyl chloride (1,15 g, 7.6 mmol) and imidazole (0.69 g, 10.2 mmol). The mixture was stirred at room temperature overnight. Upon quenching with 1 M sulfuric acid solution, the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccccc1 | HCl | CN(C=O)C | null | 8 | CC(C)(C)[Si](C)(C)Cl.COc1cc(C(C)=O)cc(OC)c1O>CN(C=O)C>COc1cc(C(C)=O)cc(OC)c1O[Si](C)(C)C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7211d0c745c549738a94877ba304ff6d | COc1cc(C(C)=O)cc(OC)c1O[Si](C)(C)C(C)(C)C.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=CC(=O)c1cc(OC)c(O[Si](C)(C)C(C)(C)C)c(OC)c1 | C(C)(C)[N-]C(C)C.[Li+].S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)OC)OC)C=CC=C2.COC=1C=C(C=C(C1O[Si](C)(C)C(C)(C)C)OC)C(C)=O>>S1C2=C(C=C1C=1C(=CC(=C(C1)C=CC(=O)C1=CC(=C(C(=C1)OC)O[Si](C)(C)C(C)(C)C)OC)OC)OC)C=CC=C2 | [CH3:21][C:22](=[O:23])[c:24]1[cH:25][c:26]([O:27][CH3:28])[c:29]([O:30][Si:31]([CH3:32])([CH3:33])[C:34]([CH3:35])([CH3:36])[CH3:37])[c:38]([O:39][CH3:40])[cH:41]1.O=[CH:20][c:19]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[s:17]2)[cH:18]1>>[CH3:1][O:2][c:... | COc1cc(C(C)=O)cc(OC)c1O[Si](C)(C)C(C)(C)C.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O | COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=CC(=O)c1cc(OC)c(O[Si](C)(C)C(C)(C)C)c(OC)c1 | null | null | O1CCCC1 | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(C=Cc1cccc(-c2cc3ccccc3s2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])-[CH;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 20 | [{"value": 20.0, "product": "S1C2=C(C=C1C=1C(=CC(=C(C1)C=CC(=O)C1=CC(=C(C(=C1)OC)O[Si](C)(C)C(C)(C)C)OC)OC)OC)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Ex-59B: To a solution of 3′,5′-dimethoxy-4′-(tert-butyldimethylsiloxy)acetophenone, from Ex-59A (0.5 g, 1.6 mmol) in tetrahydrofuran (10 mL) chilled with ice/water was added lithium diisopropylamide (2 M, 0.8 mL, 1.6 mmol). The mixture was stirred for 20 minutes while chilled. Then 5-(benzo[b]thien-2-yl)-2,4-dimethoxyb... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccc2sccc2c1.c1ccccc1 | HO- | O1CCCC1 | null | 0.333333 | COc1cc(C(C)=O)cc(OC)c1O[Si](C)(C)C(C)(C)C.COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O>O1CCCC1>COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=CC(=O)c1cc(OC)c(O[Si](C)(C)C(C)(C)C)c(OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4c4e46db8cf141edbd9902f9bd36d633 | COC1=C(O[SiH3])C(C(=O)C=Cc2cc(-c3cc4ccccc4s3)c(OC)cc2OC)C(C)(C)C(OC)=C1C(C)(C)C>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=CC(=O)c1cc(OC)c(O)c(OC)c1 | S1C2=C(C=C1C=1C(=CC(=C(C1)C=CC(=O)C1C(=C(C(=C(C1(C)C)OC)C(C)(C)C)OC)O[SiH3])OC)OC)C=CC=C2.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC.O1CCCC1>>S1C2=C(C=C1C=1C(=CC(=C(C1)C=CC(=O)C1=CC(=C(C(=C1)OC)O)OC)OC)OC)C=CC=C2 | CC(C)(C)[C:25]1=[C:26]([O:27][CH3:28])[C:34](C)(C)[CH:24]([C:22]([CH:21]=[CH:20][c:19]2[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]3[cH:10][c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]4[s:17]3)[cH:18]2)=[O:23])[C:31]([O:32][SiH3])=[C:29]1[O:30][CH3:33]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[c... | COC1=C(O[SiH3])C(C(=O)C=Cc2cc(-c3cc4ccccc4s3)c(OC)cc2OC)C(C)(C)C(OC)=C1C(C)(C)C | COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=CC(=O)c1cc(OC)c(O)c(OC)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 29ddbc8423b0fa3458daa9ba69e19baa703f62fadf1e6e8f61328f5a7c67b877 | 049fcc0c22defb2af711e7312f2f90383f80c333f7d8cf0e6c6e9942cae1c523 | O=C(C=Cc1cccc(-c2cc3ccccc3s2)c1)c1ccccc1 | C-C(-C)(-C)-[C;H0;D3;+0:1]1=[C;H0;D3;+0:2](-[#8:3]-[C;D1;H3:4])-[C;H0;D4;+0:5](-C)(-C)-[CH;D3;+0:6](-[C:7](=[O;D1;H0:8])-[C:9]=[C:10]-[c:11])-[C;H0;D3;+0:12](-[O;H0;D2;+0:13]-[SiH3])=[C;H0;D3;+0:14]-1-[O;H0;D2;+0:15]-[CH3;D1;+0:16]>>[C;D1;H3:4]-[#8:3]-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[c;H0;D3;+0:6](-[C:7](=[O;D1;H0:8])-[C:... | 46 | [{"value": 46.0, "product": "S1C2=C(C=C1C=1C(=CC(=C(C1)C=CC(=O)C1=CC(=C(C(=C1)OC)O)OC)OC)OC)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-[5-(benzo[b]thien-2-yl)2,4-dimethoxyphenyl]-1-(4-tert-butyldimethyl-siloxy-3,5-dimethoxyphenyl)-2-propen-1-one, from Ex-59B, (0.135 g, 0.228 mmol) in tetrahydrofuran (2 mL) was added tetrabutylammonium fluoride (0.061 g. 0.228 mmol), and the mixture was stirred at room temperature for two hours. Upon... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether | Ketone.Ether.Ether.Aromatic alcohol | C1=CCCC=C1 | c1ccccc1 | c1ccccc1.c1ccc2sccc2c1.c1ccccc1 | Other | null | null | 2 | COC1=C(O[SiH3])C(C(=O)C=Cc2cc(-c3cc4ccccc4s3)c(OC)cc2OC)C(C)(C)C(OC)=C1C(C)(C)C>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=CC(=O)c1cc(OC)c(O)c(OC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1a6cab735b784644a4361ba81a9aa295 | CCOC(=O)CO.COc1cc(C(C)=O)cc(OC)c1O>>CCOC(=O)c1c(OC)cc(C(=O)COC)cc1OC | COC=1C=C(C=C(C1O)OC)C(C)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(CO)(=O)OCC.CCOC(=O)/N=N/C(=O)OCC>>C(C)OC(=O)C1=C(C=C(C=C1OC)C(COC)=O)OC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:16][OH:15].O[c:6]1[c:7]([O:8][CH3:9])[cH:10][c:11]([C:12](=[O:13])[CH3:14])[cH:17][c:18]1[O:19][CH3:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([O:8][CH3:9])[cH:10][c:11]([C:12](=[O:13])[CH2:14][O:15][CH3:16])[cH:17][c:18]1[O:19][CH3:20] | CCOC(=O)CO.COc1cc(C(C)=O)cc(OC)c1O | CCOC(=O)c1c(OC)cc(C(=O)COC)cc1OC | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 4646b155988172b242d5137347c3b0b0feb8517577e33604b4123e53cd998f06 | 64fc23516941529f5dd54811af89d2b2e13a2dfe6a8d6790d171b8db884686ba | c1ccccc1 | O-[c;H0;D3;+0:1]1:[c:2](-[#8:3]):[c:4]:[c:5](-[C:6](-[CH3;D1;+0:7])=[O;D1;H0:8]):[c:9]:[c:10]:1-[#8:11].[C:12]-[#8:13]-[C;H0;D3;+0:14](=[O;D1;H0:15])-[CH2;D2;+0:16]-[OH;D1;+0:17]>>[#8:3]-[c:2]1:[c:4]:[c:5](-[C:6](=[O;D1;H0:8])-[CH2;D2;+0:7]-[O;H0;D2;+0:17]-[CH3;D1;+0:16]):[c:9]:[c:10](-[#8:11]):[c;H0;D3;+0:1]:1-[C;H0;D... | 35.9 | [{"value": 35.9, "product": "C(C)OC(=O)C1=C(C=C(C=C1OC)C(COC)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-61A: 3′,5′-Dimethoxy-4′-hydroxyacetophenone (6.03 g, 31 mmol) and triphenylphosphine (8.05 g, 31 mmol) were stirred in 124 mL of tetrahydrofuran (THF). The mixture was treated with ethyl glycolate (3.2 g, 31 mmol) and diethylazodicarboxylate (4.83 mL, 31 mmol). The reaction mixture was stirred under reflux for about... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary alcohol.Aromatic alcohol | Ketone.Ester.Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | O1CCCC1 | null | null | CCOC(=O)CO.COc1cc(C(C)=O)cc(OC)c1O>O1CCCC1>CCOC(=O)c1c(OC)cc(C(=O)COC)cc1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-772d75e44f814447a810e085fd5bd9f5 | BrBr.COc1ccc(C=O)c(O)c1>>COc1cc(O)c(C=O)cc1Br | OC1=C(C=O)C=CC(=C1)OC.BrBr>>BrC=1C(=CC(=C(C=O)C1)O)OC | Br[Br:12].[CH3:1][O:2][c:3]1[cH:4][c:5]([OH:6])[c:7]([CH:8]=[O:9])[cH:10][cH:11]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([OH:6])[c:7]([CH:8]=[O:9])[cH:10][c:11]1[Br:12] | BrBr.COc1ccc(C=O)c(O)c1 | COc1cc(O)c(C=O)cc1Br | null | null | ClCCl.CCOC(=O)C | Functional Group Interconversion | Bromination | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Br-[Br;H0;D1;+0:1].[#8:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]-[C:8]=[O;D1;H0:9]>>[#8:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[Br;H0;D1;+0:1]):[c:6]:[c:7]-[C:8]=[O;D1;H0:9] | 84.4 | [{"value": 84.4, "product": "BrC=1C(=CC(=C(C=O)C1)O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1.5 | HOUR | Ex-62A: A solution of 2-hydroxy-4-methoxybenzaldehyde (3.03 g, 20 mmol) in 25 mL of dichloromethane was cooled to 0° C. and treated dropwise with a solution of bromine (3.41 g, 21 mmol) in 10 mL of dichloromethane. The reaction mixture was stirred at 0° C. for 1.5 hours. The solvent was removed by rotary evaporation to... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | ClCCl.CCOC(=O)C | 0 | 1.5 | BrBr.COc1ccc(C=O)c(O)c1>ClCCl.CCOC(=O)C>COc1cc(O)c(C=O)cc1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3fdfa8d9995e4854b76f9b05e10b3ae5 | COc1cc(O)c(C=O)cc1Br.OB(O)c1cccs1>>COc1cc(O)c(C=O)cc1-c1cc2ccccc2s1 | N#N.BrC=1C(=CC(=C(C=O)C1)O)OC.S1C(=CC=C1)B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>>S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)O)OC)C=CC=C2 | Br[c:11]1[c:3]([O:2][CH3:1])[cH:4][c:5]([OH:6])[c:7]([CH:8]=[O:9])[cH:10]1.OB(O)[c:19]1[cH:18][cH:17][cH:12][s:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([OH:6])[c:7]([CH:8]=[O:9])[cH:10][c:11]1-[c:12]1[cH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[s:20]1 | COc1cc(O)c(C=O)cc1Br.OB(O)c1cccs1 | COc1cc(O)c(C=O)cc1-c1cc2ccccc2s1 | null | null | COCCOC | C-C Coupling | OtherReaction | 379ca588d522115c6f78ef009bec73b75a2690147aebc41a5faed8ff07b4966b | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3ccccc3s2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].O-B(-O)-[c;H0;D3;+0:9]1:[#16;a:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:[c:13]:1>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[c;H0;D3;+0:11]1:[#16;a:10]:[c;H0;D3;+0:9]2:[c:13]:[cH;D2;+0:12]:[c:14]:[c:15]:[c:16]:2:[c:17]:1):[c:2]:[c:3]-[C:4]=[O;D1;H0:5] | 170.1 | [{"value": 170.1, "product": "S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)O)OC)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Ex-62B: A stream of N2 was bubbled through a solution of 5-bromo-2-hydroxy-4-methoxybenzaldehyde (1 g, 4.3 mmol) from Ex-62A in 30 mL of ethylene glycol dimethyl ether for 15 min. Tetrakis-triphenylphosphine palladium (0) (0.5 g, 0.4 mmol) was added along with thiophene-2-boronic acid (1.2 g, 6.5 mmol) and 10 mL of Na2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccc2sccc2c1 | c1ccccc1.c1ccc2sccc2c1 | null | COCCOC | null | null | COc1cc(O)c(C=O)cc1Br.OB(O)c1cccs1>COCCOC>COc1cc(O)c(C=O)cc1-c1cc2ccccc2s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-53ea9cf14a8744f78909ae696f4bfac7 | C=COC(C)=O.CCCCOC(=O)c1ccccc1C(=O)OCCCC>>C=CCOC(=O)c1ccccc1C(=O)OCC=C | C(C=1C(C(=O)OCCCC)=CC=CC1)(=O)OCCCC.S(=O)(=O)([O-])OOS(=O)(=O)[O-].[NH4+].[NH4+].C(C)(=O)OC=C.C(C=1C(C(=O)OCCCC)=CC=CC1)(=O)OCCCC>>C(C=1C(C(=O)OCC=C)=CC=CC1)(=O)OCC=C | CC(=O)O[CH:2]=[CH2:1].CCC[CH2:3][O:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[C:13](=[O:14])[O:15][CH2:16][CH2:17][CH2:18]C>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][c:12]1[C:13](=[O:14])[O:15][CH2:16][CH:17]=[CH2:18] | C=COC(C)=O.CCCCOC(=O)c1ccccc1C(=O)OCCCC | C=CCOC(=O)c1ccccc1C(=O)OCC=C | null | null | O | C-C Coupling | OtherReaction | 5704e0572b2792055ea7ace0ab9d5c08e91a5bd5208446dc90bb3e4d4b22231a | e1ec59b264f7681b281d160d0ca665e90513d6835010c1042b2b30c575374e30 | c1ccccc1 | C-C(=O)-O-[CH;D2;+0:1]=[C;D1;H2:2].C-C-C-[CH2;D2;+0:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c:7].C-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[C:10]-[#8:11]-[C:12]=[O;D1;H0:13]>>[C;D1;H2:2]=[CH;D2;+0:1]-[CH2;D2;+0:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c:7].[CH2;D1;+0:8]=[CH;D2;+0:9]-[C:10]-[#8:11]-[C:12]=[O;D1;H0:13] | null | [] | 80 | CELSIUS | 5 | MINUTE | 0.2 g of defoamer and 12 g of Fixapret COC were added to and mixed with a solution of 47 g of polyvinyl alcohol in 600 g of water. The mixture was heated to about 80° C. About 90% of a catalyst solution of 1.3 g of ammonium persulfate in 6 g of water were then added and the mixture was homogenized for about 5 minutes. ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Vinyl | Ester.Allyl.Allyl | null | null | c1ccccc1 | HO- | O | 80 | 0.083333 | C=COC(C)=O.CCCCOC(=O)c1ccccc1C(=O)OCCCC>O>C=CCOC(=O)c1ccccc1C(=O)OCC=C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-15ed3afbed324fc5a0787f9298282063 | CC(C)(C)c1cc(CCN)cc(C(C)(C)C)c1O.CCCCOc1cc(C=CC(=O)O)cc(OCCCC)c1O>>CCCCOc1cc(C=CC(=O)NCCc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc(OCCCC)c1O | C1CCC(CC1)N=C=NC2CCCCC2.C(CCC)OC=1C=C(C=C(C1O)OCCCC)C=CC(=O)O.NCCC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C.C=1C=CC2=C(C1)N=NN2O>>C(CCC)OC=1C=C(C=C(C1O)OCCCC)C=CC(=O)NCCC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C | [NH2:13][CH2:14][CH2:15][c:16]1[cH:17][c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[c:23]([OH:24])[c:25]([C:26]([CH3:27])([CH3:28])[CH3:29])[cH:30]1.O[C:11]([CH:10]=[CH:9][c:8]1[cH:7][c:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:38]([OH:39])[c:32]([O:33][CH2:34][CH2:35][CH2:36][CH3:37])[cH:31]1)=[O:12]>>[CH3:1][CH2:2][CH2:3]... | CC(C)(C)c1cc(CCN)cc(C(C)(C)C)c1O.CCCCOc1cc(C=CC(=O)O)cc(OCCCC)c1O | CCCCOc1cc(C=CC(=O)NCCc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc(OCCCC)c1O | null | null | CC#N | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(C=Cc1ccccc1)NCCc1ccccc1 | 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] | 91.5 | [{"value": 91.0, "product": "C(CCC)OC=1C=C(C=C(C1O)OCCCC)C=CC(=O)NCCC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.5, "product": "C(CCC)OC=1C=C(C=C(C1O)OCCCC)C=CC(=O)NCCC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To the solution of 3-(3,5-dibutoxy-4-hydroxyphenyl)acrylic acid (130 mg, 0.421 mmol), 4-(2-aminoethyl)-2,6-di-t-butylphenol (110 mg, 0.441 mmol) and HOBT (70 mg, 0.51 mmol) in MeCN 10 ml were DCC at 0° C. After 5 minutes, the solution was stirred for 2 hours at room temperature. And then the precipitate was removed by ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CC#N | null | 0.083333 | CC(C)(C)c1cc(CCN)cc(C(C)(C)C)c1O.CCCCOc1cc(C=CC(=O)O)cc(OCCCC)c1O>CC#N>CCCCOc1cc(C=CC(=O)NCCc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc(OCCCC)c1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9510d77d582b450d883ef78c542b5bab | CC(C)(C)c1cc(CCN)cc(C(C)(C)C)c1O.CCCCOc1cc(C=CC(=O)O)cc(OCCCC)c1O.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C>>CCCCOc1cc(C=CC(=O)NCCCCc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc(OCCCC)c1O | F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(CCC)OC=1C=C(C=C(C1O)OCCCC)C=CC(=O)O.NCCC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C>>C(CCC)OC=1C=C(C=C(C1O)OCCCC)C=CC(=O)NCCCCC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C | [NH2:13][CH2:14][CH2:17][c:18]1[cH:19][c:20]([C:21]([CH3:22])([CH3:23])[CH3:24])[c:25]([OH:26])[c:27]([C:28]([CH3:29])([CH3:30])[CH3:31])[cH:32]1.O[C:11]([CH:10]=[CH:9][c:8]1[cH:7][c:6]([O:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:40]([OH:41])[c:34]([O:35][CH2:36][CH2:37][CH2:38][CH3:39])[cH:33]1)=[O:12].CN(C)[P+](On1nnc2cc[cH... | CC(C)(C)c1cc(CCN)cc(C(C)(C)C)c1O.CCCCOc1cc(C=CC(=O)O)cc(OCCCC)c1O.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C | CCCCOc1cc(C=CC(=O)NCCCCc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc(OCCCC)c1O | null | null | CCN(CC)CC.CN(C)C=O.C(Cl)Cl | Acylation | OtherReaction | a24117a319ae7f7ed0e2138d9be038d04bd20f7709e3d139967549efb1cd97fb | 6f35efba33558ef5fc3cd84a18d45a4f1577b28d410f08768b27ebd3b689ecd0 | O=C(C=Cc1ccccc1)NCCCCc1ccccc1 | C-N(-C)-[P+](-O-n1:n:n:c2:c:c:[cH;D2;+0:1]:[cH;D2;+0:2]:c:2:1)(-N(-C)-C)-N(-C)-C.O-[C;H0;D3;+0:3](=[O;D1;H0:4])-[C:5]=[C:6]-[c:7].[NH2;D1;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[O;D1;H0:4]=[C;H0;D3;+0:3](-[C:5]=[C:6]-[c:7])-[NH;D2;+0:8]-[CH2;D2;+0:9]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:10]-[c:11]... | 91 | [{"value": 91.0, "product": "C(CCC)OC=1C=C(C=C(C1O)OCCCC)C=CC(=O)NCCCCC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.8, "product": "C(CCC)OC=1C=C(C=C(C1O)OCCCC)C=CC(=O)NCCCCC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To the solution of 3-(3,5-dibutoxy-4-hydroxyphenyl) acrylic acid (53 mg, 0.17 mmol) in DMF (0.76 ml) and Et3N (39 μl), was added 4-(2-aminoethyl)-2,6-di-t-butylphenol (50 mg, 0.19 mmol) at 0° C. The obtained solution was added with the solution of benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphate... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Tertiary amine.Tertiary amine.Tertiary amine | Secondary amide | c1ccc2[nH]nnc2c1 | null | c1ccccc1.c1ccccc1 | HO- | CCN(CC)CC.CN(C)C=O.C(Cl)Cl | 0 | 0.5 | CC(C)(C)c1cc(CCN)cc(C(C)(C)C)c1O.CCCCOc1cc(C=CC(=O)O)cc(OCCCC)c1O.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C>CCN(CC)CC.CN(C)C=O.C(Cl)Cl>CCCCOc1cc(C=CC(=O)NCCCCc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc(OCCCC)c1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7feb93247a2c4c19a4a523417a2e1545 | CCC(CC)Oc1cc(C=CC(=O)O)cc(OC(CC)CC)c1O.Cc1ccc(CCCN)cc1C>>CCC(CC)Oc1cc(C=CC(=O)NCCCc2ccc(C)c(C)c2)cc(OC(CC)CC)c1O | C(C)C(CC)OC=1C=C(C=C(C1O)OC(CC)CC)C=CC(=O)O.CC=1C=C(C=CC1C)CCCN.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C>>C(C)C(CC)OC=1C=C(C=C(C1O)OC(CC)CC)C=CC(=O)NCCCC1=CC(=C(C=C1)C)C | O[C:12]([CH:11]=[CH:10][c:9]1[cH:8][c:7]([O:6][CH:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[c:34]([OH:35])[c:27]([O:28][CH:29]([CH2:30][CH3:31])[CH2:32][CH3:33])[cH:26]1)=[O:13].[NH2:14][CH2:15][CH2:16][CH2:17][c:18]1[cH:19][cH:20][c:21]([CH3:22])[c:23]([CH3:24])[cH:25]1>>[CH3:1][CH2:2][CH:3]([CH2:4][CH3:5])[O:6][c:7]1[cH:8][c... | CCC(CC)Oc1cc(C=CC(=O)O)cc(OC(CC)CC)c1O.Cc1ccc(CCCN)cc1C | CCC(CC)Oc1cc(C=CC(=O)NCCCc2ccc(C)c(C)c2)cc(OC(CC)CC)c1O | null | null | CCN(CC)CC.C(Cl)Cl.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(C=Cc1ccccc1)NCCCc1ccccc1 | 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] | 90 | [{"value": 90.0, "product": "C(C)C(CC)OC=1C=C(C=C(C1O)OC(CC)CC)C=CC(=O)NCCCC1=CC(=C(C=C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.0, "product": "C(C)C(CC)OC=1C=C(C=C(C1O)OC(CC)CC)C=CC(=O)NCCCC1=CC(=C(C=C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To the solution of 3-[3,5-bis-(1-ethylpropoxy)-4-hydroxyphenyl]acrylic acid (20 mg, 0.06 mmol) in DMF (0.2 ml) and Et3N (10 μl), was added 3(3,4-dimethylphenyl)propylamine (11 mg, 0.07 mmol) at 0° C. and was added the solution of BOP (29 mg, 0.07 mmol) in CH2Cl2 (0.2 ml). The solution was stirred for 30 minutes at 0° C... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CCN(CC)CC.C(Cl)Cl.CN(C)C=O | 0 | 0.5 | CCC(CC)Oc1cc(C=CC(=O)O)cc(OC(CC)CC)c1O.Cc1ccc(CCCN)cc1C>CCN(CC)CC.C(Cl)Cl.CN(C)C=O>CCC(CC)Oc1cc(C=CC(=O)NCCCc2ccc(C)c(C)c2)cc(OC(CC)CC)c1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7ef39f94167d459b9c350cc232bd33b7 | CC(C)(C)c1cc(CN)cc(C(C)(C)C)c1O.CCC(CC)Oc1cc(C=CC(=O)O)cc(OC(CC)CC)c1O>>CCC(CC)Oc1cc(C=CC(=O)NCc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc(OC(CC)CC)c1O | C(C)C(CC)OC=1C=C(C=C(C1O)OC(CC)CC)C=CC(=O)O.NCC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C>>C(C)C(CC)OC=1C=C(C=C(C1O)OC(CC)CC)C=CC(=O)NCC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C | [NH2:14][CH2:15][c:16]1[cH:17][c:18]([C:19]([CH3:20])([CH3:21])[CH3:22])[c:23]([OH:24])[c:25]([C:26]([CH3:27])([CH3:28])[CH3:29])[cH:30]1.O[C:12]([CH:11]=[CH:10][c:9]1[cH:8][c:7]([O:6][CH:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[c:39]([OH:40])[c:32]([O:33][CH:34]([CH2:35][CH3:36])[CH2:37][CH3:38])[cH:31]1)=[O:13]>>[CH3:1][CH2... | CC(C)(C)c1cc(CN)cc(C(C)(C)C)c1O.CCC(CC)Oc1cc(C=CC(=O)O)cc(OC(CC)CC)c1O | CCC(CC)Oc1cc(C=CC(=O)NCc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc(OC(CC)CC)c1O | null | null | CCN(CC)CC.C(Cl)Cl.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(C=Cc1ccccc1)NCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]=[C:4]-[c:5])-[NH;D2;+0:6]-[C:7]-[c:8] | 50.2 | [{"value": 50.0, "product": "C(C)C(CC)OC=1C=C(C=C(C1O)OC(CC)CC)C=CC(=O)NCC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.2, "product": "C(C)C(CC)OC=1C=C(C=C(C1O)OC(CC)CC)C=CC(=O)NCC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": f... | 0 | CELSIUS | 30 | MINUTE | To the solution of 3-[3,5-bis-(1-ethylpropoxy)-4-hydroxyphenyl]acrylic acid (30 mg, 0.09 mmol) in DMF (0.2 ml) and Et3N (10 μl), was added 4-aminomethyl-2,6-di-t-butylphenol (23 mg, 0.10 mmol) at 0° C. and was added the solution of BOP (44 mg, 0.10 mmol) in CH2Cl2 (0.6 ml). The solution was stirred for 30 minutes at 0°... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CCN(CC)CC.C(Cl)Cl.CN(C)C=O | 0 | 0.5 | CC(C)(C)c1cc(CN)cc(C(C)(C)C)c1O.CCC(CC)Oc1cc(C=CC(=O)O)cc(OC(CC)CC)c1O>CCN(CC)CC.C(Cl)Cl.CN(C)C=O>CCC(CC)Oc1cc(C=CC(=O)NCc2cc(C(C)(C)C)c(O)c(C(C)(C)C)c2)cc(OC(CC)CC)c1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b8d388da673d433cbe34ec1ef9a357e2 | CC(C)(C)c1ccc(CCCCN)c(C(C)(C)C)c1O.CCC(CC)Oc1cc(C=CC(=O)O)cc(OC(CC)CC)c1O>>C=C(C(=O)NCCCCc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1)c1cc(OC(CC)CC)c(O)c(OC(CC)CC)c1 | C(C)C(CC)OC=1C=C(C=C(C1O)OC(CC)CC)C=CC(=O)O.NCCCCC=1C(=C(C(=CC1)C(C)(C)C)O)C(C)(C)C.CN(C)C=O.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C>>C(C)C(CC)OC=1C=C(C=C(C1O)OC(CC)CC)C(C(=O)NCCCCC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)=C | [NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][c:10]1[cH:11][cH:12][c:17]([C:13]([CH3:14])([CH3:15])[CH3:16])[c:19]([OH:18])[c:24]1[C:20]([CH3:21])([CH3:22])[CH3:23].O[C:3]([CH:2]=[CH:1][c:25]1[cH:26][c:27]([O:28][CH:29]([CH2:30][CH3:31])[CH2:32][CH3:33])[c:34]([OH:35])[c:36]([O:37][CH:38]([CH2:39][CH3:40])[CH2:41][CH3:42])[cH:43... | CC(C)(C)c1ccc(CCCCN)c(C(C)(C)C)c1O.CCC(CC)Oc1cc(C=CC(=O)O)cc(OC(CC)CC)c1O | C=C(C(=O)NCCCCc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1)c1cc(OC(CC)CC)c(O)c(OC(CC)CC)c1 | null | null | CCN(CC)CC.C(Cl)Cl | Acylation | OtherReaction | add518fe46c2080b2e0073b1d5e90b43f22106f49c1c4ba985fd805ec54d04e4 | f73dd9323138d95383e7f39d832ec654c389295c6cf7ce02912884ce088ed6f6 | C=C(C(=O)NCCCCc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D2;+0:3]=[CH;D2;+0:4]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[C:10]-[C:11]-[NH2;D1;+0:12].[C:13]-[c:14]1:[c:15]:[cH;D2;+0:16]:[c;H0;D3;+0:17](-[C;H0;D4;+0:18](-[C;D1;H3:19])(-[C;D1;H3:20])-[C;D1;H3:21]):[c;H0;D3;+0:22](-[OH;D1;+0:23]):[c;H0;D3;+0:24]:1-[C;H0;D4;+0:25](-[C;D1;H3:26])... | 90 | [{"value": 90.0, "product": "C(C)C(CC)OC=1C=C(C=C(C1O)OC(CC)CC)C(C(=O)NCCCCC1=CC(=C(C(=C1)C(C)(C)C)O)C(C)(C)C)=C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To the solution of 3-[3,5-bis-(1-ethylpropoxy)-4-hydroxyphenyl]acrylic acid (30 mg, 0.09 mmol) in DMF (0.6 ml) and Et3N (13 μl) was added 4-(4-aminobutyl-2,6-di-t-butylphenol (28 mg, 0.10 mmol) at 0° C. and was added the solution of BOP (44 mg, 0.10 mmol) in CH2Cl2 (0.6 ml). The solution was stirred for 30 minutes at 0... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | Secondary amide.Aromatic alcohol.Vinyl | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | CCN(CC)CC.C(Cl)Cl | 0 | 0.5 | CC(C)(C)c1ccc(CCCCN)c(C(C)(C)C)c1O.CCC(CC)Oc1cc(C=CC(=O)O)cc(OC(CC)CC)c1O>CCN(CC)CC.C(Cl)Cl>C=C(C(=O)NCCCCc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1)c1cc(OC(CC)CC)c(O)c(OC(CC)CC)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ea81dd70bcd34b8da3a095b9c3d2d22e | CCCCCCOc1cc(C=CC(=O)O)cc(OCCCCCC)c1O.Nc1ccccc1O>>CCCCCCOc1cc(C=CC(=O)Nc2ccccc2O)cc(OCCCCCC)c1O | C(CCCCC)OC=1C=C(C=C(C1O)OCCCCCC)C=CC(=O)O.NC1=C(C=CC=C1)O.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C>>C(CCCCC)OC=1C=C(C=C(C1O)OCCCCCC)C=CC(=O)NC1=C(C=CC=C1)O | O[C:13]([CH:12]=[CH:11][c:10]1[cH:9][c:8]([O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:32]([OH:33])[c:24]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[cH:23]1)=[O:14].[NH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[OH:22]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][c:10]([CH:11]=[CH... | CCCCCCOc1cc(C=CC(=O)O)cc(OCCCCCC)c1O.Nc1ccccc1O | CCCCCCOc1cc(C=CC(=O)Nc2ccccc2O)cc(OCCCCCC)c1O | null | null | CCN(CC)CC.C(Cl)Cl.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(C=Cc1ccccc1)Nc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[C:3]=[C:4]-[c:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 34 | [{"value": 34.0, "product": "C(CCCCC)OC=1C=C(C=C(C1O)OCCCCCC)C=CC(=O)NC1=C(C=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.9, "product": "C(CCCCC)OC=1C=C(C=C(C1O)OCCCCCC)C=CC(=O)NC1=C(C=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To the solution of 3-(3,5-bishexyloxy-4-hydroxyphenyl) acrylic acid (40 mg, 0.11 mmol) in DMF (1 ml) and Et3N (17 μl), was added 2-aminophenol (13 mg, 0.12 mmol) at 0° C. and was added the solution of BOP (53 mg, 0.12 mmol) in CH2Cl2 (0.6 ml). The solution was stirred for 30 minutes at 0° C. and then was stirred for 1.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1 | HO- | CCN(CC)CC.C(Cl)Cl.CN(C)C=O | 0 | 0.5 | CCCCCCOc1cc(C=CC(=O)O)cc(OCCCCCC)c1O.Nc1ccccc1O>CCN(CC)CC.C(Cl)Cl.CN(C)C=O>CCCCCCOc1cc(C=CC(=O)Nc2ccccc2O)cc(OCCCCCC)c1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-775e1765b7fa43c09871eef7ae04f3c2 | CCCCCOc1cc(CO)cc(OCCCCC)c1O.O=C(CN1CCNCC1)c1ccc(F)cc1>>CCCCCOc1cc(CN2CCN(CC(=O)c3ccc(F)cc3)CC2)cc(OCCCCC)c1O | N(=NC(=O)OCC)C(=O)OCC.OCC1=CC(=C(C(=C1)OCCCCC)O)OCCCCC.FC1=CC=C(C=C1)C(CN1CCNCC1)=O.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>FC1=CC=C(C=C1)C(CN1CCN(CC1)CC1=CC(=C(C(=C1)OCCCCC)O)OCCCCC)=O | O[CH2:10][c:9]1[cH:8][c:7]([O:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:35]([OH:36])[c:28]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[cH:27]1.[NH:11]1[CH2:12][CH2:13][N:14]([CH2:15][C:16](=[O:17])[c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]2)[CH2:25][CH2:26]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:... | CCCCCOc1cc(CO)cc(OCCCCC)c1O.O=C(CN1CCNCC1)c1ccc(F)cc1 | CCCCCOc1cc(CN2CCN(CC(=O)c3ccc(F)cc3)CC2)cc(OCCCCC)c1O | null | null | O.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 9885b3f1c049b08208f7467939360b5e493f0f916b8555f394ab4272f7b37bd7 | 87693a475e46c41583976158ec46dcaf8be8cc05c5635654a6a68033770f8d5c | O=C(CN1CCN(Cc2ccccc2)CC1)c1ccccc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1):[c:4] | 15.9 | [{"value": 15.0, "product": "FC1=CC=C(C=C1)C(CN1CCN(CC1)CC1=CC(=C(C(=C1)OCCCCC)O)OCCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.9, "product": "FC1=CC=C(C=C1)C(CN1CCN(CC1)CC1=CC(=C(C(=C1)OCCCCC)O)OCCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To the solution of 4-hydroxymethyl-2,6-bis-pentyloxyphenol (525 mg, 1.62 mmol), 1-(4-fluorophenyl)-2-piperazine-1-yl-ethanone (432 mg, 1.94 mmol) and PPh3 (509 mg, 1.94 mmol) in drying THF (10 ml) was dropped diethyl azodicarboxylate (0.38 ml, 2.43 mmol) at 0° C. and then was stirred 15 minutes at room temperature. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | O.C1CCOC1 | null | 0.25 | CCCCCOc1cc(CO)cc(OCCCCC)c1O.O=C(CN1CCNCC1)c1ccc(F)cc1>O.C1CCOC1>CCCCCOc1cc(CN2CCN(CC(=O)c3ccc(F)cc3)CC2)cc(OCCCCC)c1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-87cdbd6209e34c60b3fe63b0dfcb5ba8 | CCCCCCCCCOc1cc(C(=O)O)cc(OCCCCCCCCC)c1O.O=C(CN1CCNCC1)c1ccc(Cl)cc1>>CCCCCOc1cc(C(=O)N2CCN(CC(=O)c3ccc(Cl)cc3)CC2)cc(OCCCCC)c1O | OC1=C(C=C(C(=O)O)C=C1OCCCCCCCCC)OCCCCCCCCC.ClC1=CC=C(C=C1)C(CN1CCNCC1)=O.CCN=C=NCCCN(C)C.C=1C=CC2=C(C1)N=NN2O.C(=O)(O)[O-].[Na+]>>ClC1=CC=C(C=C1)C(CN1CCN(CC1)C(C1=CC(=C(C(=C1)OCCCCC)O)OCCCCC)=O)=O | CCCC[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][O:30][c:29]1[cH:28][c:9]([C:10](O)=[O:11])[cH:8][c:7]([O:6][CH2:5][CH2:4][CH2:3]CCCC[CH2:2][CH3:1])[c:36]1[OH:37].[NH:12]1[CH2:13][CH2:14][N:15]([CH2:16][C:17](=[O:18])[c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]2)[CH2:26][CH2:27]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][... | CCCCCCCCCOc1cc(C(=O)O)cc(OCCCCCCCCC)c1O.O=C(CN1CCNCC1)c1ccc(Cl)cc1 | CCCCCOc1cc(C(=O)N2CCN(CC(=O)c3ccc(Cl)cc3)CC2)cc(OCCCCC)c1O | null | null | CC#N | Acylation | OtherReaction | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CN1CCN(C(=O)c2ccccc2)CC1)c1ccccc1 | C-C-C-C-[CH2;D2;+0:1]-[C:2]-[C:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8].[C:9]-[C:10]-[CH2;D2;+0:11]-C-C-C-C-[CH2;D2;+0:12]-[C;D1;H3:13].[#7:14]1-[C:15]-[C:16]-[NH;D2;+0:17]-[C:18]-[C:19]-1>>[C:9]-[C:10]-[CH2;D2;+0:11]-[CH2;D2;+0:12]-[C;D1;H3:13].[C:3]-[C:2]-[CH3;D1;+0:1].[O;D1;H0:5]=[C;H0;D3;+0:4](-[N;H0;D... | 80.2 | [{"value": 66.0, "product": "ClC1=CC=C(C=C1)C(CN1CCN(CC1)C(C1=CC(=C(C(=C1)OCCCCC)O)OCCCCC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.2, "product": "ClC1=CC=C(C=C1)C(CN1CCN(CC1)C(C1=CC(=C(C(=C1)OCCCCC)O)OCCCCC)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To 4-hydroxy-3,5-bis-nonyloxy benzoic acid (98 mg, 0.23 mmol), 1-(4-chlorophenyl)-2-piperazine-1-yl-ethanone (111 mg, 0.46 mmol), EDCI (89 mg, 0.46 mmol) and HOBT (63 mg, 0.46 mmol) was added MeCN (3 ml) and stirred for 1 hour at room temperature. The solution was added with NaHCO3 to finish the reaction. The solution ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | HO- | CC#N | null | 1 | CCCCCCCCCOc1cc(C(=O)O)cc(OCCCCCCCCC)c1O.O=C(CN1CCNCC1)c1ccc(Cl)cc1>CC#N>CCCCCOc1cc(C(=O)N2CCN(CC(=O)c3ccc(Cl)cc3)CC2)cc(OCCCCC)c1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-478b6b6e95b94ca99e9f4c125d01b3e1 | COC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)F)C(F)(F)F.[Li+].[OH-]>>[Li][O]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(C(F)(F)F)C(F)(F)OC | FS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(C(F)(F)F)C(F)(F)OC.O.[OH-].[Li+]>>S(=O)(=O)(O[Li])C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(C(F)(F)F)C(F)(F)OC | F[S:3](=[O:4])(=[O:5])[C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[O:18][C:19]([F:20])([C:21]([F:22])([F:23])[F:24])[C:25]([F:26])([F:27])[O:28][CH3:29].[Li+:1].[OH-:2]>>[Li:1][O:2][S:3](=[O:4])(=[O:5])[C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[C:12]([F:13])([F:14])[C:15]([F:16])([... | COC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)F)C(F)(F)F.[Li+].[OH-] | [Li][O]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(C(F)(F)F)C(F)(F)OC | null | null | O | Acylation | OtherReaction | 9710abdc9908af230f0611317212db046ddbe9e4efaeaa534f6acc066fddc190 | 0294dd03ed5eb302c97e32c7940c77344565a5370a2663785e5aa80492855f80 | null | F-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4](-[C:5])(-[F;D1;H0:6])-[F;D1;H0:7].[Li+;H0;D0:8].[OH-;D0:9]>>[C:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;H0;D2;+0:9]-[Li;H0;D1;+0:8] | null | [] | 75 | CELSIUS | null | null | A 250 mL round bottom flask was charged with FSO2(CF2)4OCF(CF3)CF2OCH3 (23.3 g, 0.048 mole) deionized water (150 g) and lithium hydroxide monohydrate (4.08 g, 0.097 mole). The resulting mixture was heated at 75° C. for about 18 hours, filtered and the aqueous solution treated with 48% aqueous HF until slightly acidic t... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonate | null | null | null | HF | O | 75 | null | COC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)F)C(F)(F)F.[Li+].[OH-]>O>[Li][O]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC(F)(C(F)(F)F)C(F)(F)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-635850a0aa144e23a987da541fe10f93 | COC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)F.[Li+].[OH-]>>[Li][O]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC | [OH-].[Li+].FS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC.O.[OH-].[Li+].C(=O)=O>>S(=O)(=O)(O[Li])C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC | F[S:3](=[O:4])(=[O:5])[C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[O:18][CH3:19].[Li+:1].[OH-:2]>>[Li:1][O:2][S:3](=[O:4])(=[O:5])[C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[O:18][CH3:19] | COC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)F.[Li+].[OH-] | [Li][O]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC | null | null | O | Acylation | OtherReaction | 9710abdc9908af230f0611317212db046ddbe9e4efaeaa534f6acc066fddc190 | 0294dd03ed5eb302c97e32c7940c77344565a5370a2663785e5aa80492855f80 | null | F-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4](-[C:5])(-[F;D1;H0:6])-[F;D1;H0:7].[Li+;H0;D0:8].[OH-;D0:9]>>[C:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;H0;D2;+0:9]-[Li;H0;D1;+0:8] | null | [] | null | null | null | null | FSO2(CF2)4OCH3 (35.8 g, 0.114 mole) was treated with lithium hydroxide monohydrate (12 g, 0.285 mole) in deionized water (150 g) at 75° C. for six hours. After cooling to room temperature, two small pieces of solid carbon dioxide (Dry Ice) were added to neutralize the excess lithium hydroxide. The water was removed by ... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonate | null | null | null | HF | O | null | null | COC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)F.[Li+].[OH-]>O>[Li][O]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-83430d7bf97247ea87fe5e124cbf925b | CCOS(=O)(=O)OCC.O=C(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)F.[F-]>>CCOC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)F | FS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(=O)F.[F-].[K+].S(=O)(=O)(OCC)OCC.O>>FS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OCC | CCOS(=O)(=O)O[CH2:2][CH3:1].[O:3]=[C:4]([F:6])[C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[C:13]([F:14])([F:15])[S:16](=[O:17])(=[O:18])[F:19].[F-:5]>>[CH3:1][CH2:2][O:3][C:4]([F:5])([F:6])[C:7]([F:8])([F:9])[C:10]([F:11])([F:12])[C:13]([F:14])([F:15])[S:16](=[O:17])(=[O:18])[F:19] | CCOS(=O)(=O)OCC.O=C(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)F.[F-] | CCOC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)F | null | CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC.[Cl-] | COCCOCCOC | Heteroatom Alkylation and Arylation | OtherReaction | 4722b19e5c0bd8859e112a70b85350ef344086146f7bcb1e59f7dbf48410cff2 | e3109f17ac6917ddf8a840cf4f3485d420243744a4438cad70cf693ceb10c490 | null | C-C-O-S(=O)(=O)-O-[CH2;D2;+0:1]-[C;D1;H3:2].[C:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C;H0;D3;+0:7](-[F;D1;H0:8])=[O;H0;D1;+0:9].[F-;H0;D0:10]>>[C:3]-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[C;H0;D4;+0:7](-[F;D1;H0:8])(-[F;H0;D1;+0:10])-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C;D1;H3:2] | 62.5 | [{"value": 62.5, "product": "FS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 2 | HOUR | In a procedure similar to that described in Preparation of Precursor 1, FSO2(CF2)3COF (70 g, 0.25 mole), KF (21.8 g, 0.37 mole), diglyme (350 ml), Adogen 464 (10.5 g of a 56% solution in anhydrous diglyme) and diethyl sulfate (48 g, 0.312 mole) were combined and reacted at 52° C. for 16 hours. Deionized water (˜250 g) ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Tertiary halide.Tertiary halide.Ether | null | null | null | HO- | CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC.[Cl-].COCCOCCOC | 65 | 2 | CCOS(=O)(=O)OCC.O=C(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)F.[F-]>CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC.[Cl-].COCCOCCOC>CCOC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dff731d31c68444588826d90699f1aeb | O=C=O.O=S(=O)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OCc1ccccc1.[Li+]>>[Li][O]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OCc1ccccc1 | C(=O)=O.[OH-].[Li+].FS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OCC1=CC=CC=C1.[OH-].[Li+].[OH-]>>S(=O)(=O)(O[Li])C(F)(F)C(F)(F)C(F)(F)C(F)(F)OCC1=CC=CC=C1 | O=C=[O:5].F[S:3](=[O:2])(=[O:4])[C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[O:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.[Li+:1]>>[Li:1][O:2][S:3](=[O:4])(=[O:5])[C:6]([F:7])([F:8])[C:9]([F:10])([F:11])[C:12]([F:13])([F:14])[C:15]([F:16])([F:17])[O:18][CH2:19][c:20]1... | O=C=O.O=S(=O)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OCc1ccccc1.[Li+] | [Li][O]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OCc1ccccc1 | null | null | CO | Acylation | OtherReaction | 729cd61c01d81e8a6c1ab70187b764caa3de36172ac606c8e518f6b48bf433e9 | 54c7635ffde4d490c1c5e4e3c5f6d7559a2be37595812791a2f3bf2f290b4267 | c1ccccc1 | F-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;H0;D1;+0:3])-[C:4](-[C:5])(-[F;D1;H0:6])-[F;D1;H0:7].O=C=[O;H0;D1;+0:8].[Li+;H0;D0:9]>>[C:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;H0;D1;+0:8])-[O;H0;D2;+0:3]-[Li;H0;D1;+0:9] | null | [] | 75 | CELSIUS | null | null | FSO2(CF2)4OCH2C6H5 was treated with excess aqueous lithium hydroxide as described in Preparation of Precursor 3 except that the solution was heated at 75° C. for eighteen hours. After neutralization of the excess hydroxide with solid carbon dioxide, it was noted that a lower fluorochemical-containing phase was still pr... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide.Carbon dioxide | Sulfonate | null | null | c1ccccc1 | Other | CO | 75 | null | O=C=O.O=S(=O)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OCc1ccccc1.[Li+]>CO>[Li][O]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)OCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8279129301e5482eb7927fbcb8008844 | O=C(O)c1cc(C(=O)O)c(C(=O)O)cc1C(=O)O>>O=C(O)C1CC(C(=O)O)C(C(=O)O)CC1C(=O)O | [H][H].[H][H].C(C=1C(C(=O)O)=CC(C(=O)O)=C(C(=O)O)C1)(=O)O.[H][H]>>C1(C(CC(C(C1)C(=O)O)C(=O)O)C(=O)O)C(=O)O | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([C:7](=[O:8])[OH:9])[c:10]([C:11](=[O:12])[OH:13])[cH:14][c:15]1[C:16](=[O:17])[OH:18]>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH:6]([C:7](=[O:8])[OH:9])[CH:10]([C:11](=[O:12])[OH:13])[CH2:14][CH:15]1[C:16](=[O:17])[OH:18] | O=C(O)c1cc(C(=O)O)c(C(=O)O)cc1C(=O)O | O=C(O)C1CC(C(=O)O)C(C(=O)O)CC1C(=O)O | null | null | O | Reduction | Arene hydrogenation | cfd1f3b98f7cd3ca3735c14f302dc0acdc6f0d4501cd6920cbb5c1a3d892ff3a | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | C1CCCCC1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]):[c;H0;D3;+0:10](-[C:11](=[O;D1;H0:12])-[O;D1;H1:13]):[cH;D2;+0:14]:[c;H0;D3;+0:15]:1-[C:16](=[O;D1;H0:17])-[O;D1;H1:18]>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D3;+0:4]1-[CH2;D2;+0:5]-[CH;D3;+0:6](-[C:7](=[O;D1;H0... | 85.1 | [{"value": 85.0, "product": "C1(C(CC(C(C1)C(=O)O)C(=O)O)C(=O)O)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.1, "product": "C1(C(CC(C(C1)C(=O)O)C(=O)O)C(=O)O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | HOUR | A 5-L Hastelloy (HC22) autoclave was charged with 552 g of pyromellitic acid, 200 g of a catalyst of Rh supported on activated carbon (available from N.E. Chemcat Corporation) and 1656 g of water, and then the inner atmosphere was replaced with nitrogen gas while stirring the contents. Then, the inner atmosphere was re... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | C1CCCCC1 | C1CCCCC1 | null | O | 60 | 2 | O=C(O)c1cc(C(=O)O)c(C(=O)O)cc1C(=O)O>O>O=C(O)C1CC(C(=O)O)C(C(=O)O)CC1C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fdaf4ca57249458b81ef5c9679d8ec9e | O=C(O)C1CC(C(=O)O)C(C(=O)O)CC1C(=O)O>>O=C1OC(=O)C2CC3C(=O)OC(=O)C3CC12 | C1(C(CC(C(C1)C(=O)O)C(=O)O)C(=O)O)C(=O)O.C(C)(=O)OC(C)=O>>C1C2C(CC3C1C(=O)OC3=O)C(=O)OC2=O | O=[C:12]([OH:13])[CH:14]1[CH:8]([C:9](=[O:10])[OH:11])[CH2:7][CH:6]([C:4]([OH:3])=[O:5])[CH:16]([C:2](O)=[O:1])[CH2:15]1>>[O:1]=[C:2]1[O:3][C:4](=[O:5])[CH:6]2[CH2:7][CH:8]3[C:9](=[O:10])[O:11][C:12](=[O:13])[CH:14]3[CH2:15][CH:16]12 | O=C(O)C1CC(C(=O)O)C(C(=O)O)CC1C(=O)O | O=C1OC(=O)C2CC3C(=O)OC(=O)C3CC12 | null | null | null | Miscellaneous | OtherReaction | fdb3db752eaeb2c80fd8515b522bc844e84deaef56e7ac5590d174386d5f1fcb | e83a95bc3ef3bbc28a0f9ce60ccfbd3725429b901b391dbfdf0df35bff2f3261 | O=C1OC(=O)C2CC3C(=O)OC(=O)C3CC12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4]-[C:5](-[C;H0;D3;+0:6](=O)-[OH;D1;+0:7])-[C:8]-[C:9](=[O;D1;H0:10])-[OH;D1;+0:11])-[C:12]-[C:13](=[O;D1;H0:14])-[OH;D1;+0:15]>>[O;D1;H0:10]=[C:9]1-[C:8]-[C:5](-[C:4]-[C:3]2-[C:12]-[C:13](=[O;D1;H0:14])-[O;H0;D2;+0:15]-[C;H0;D3;+0:1]-2=[O;D1;H0:2])-[C;H0;D3;+0:6](=[O;H0;D1;+0:7... | 96.7 | [{"value": 96.6, "product": "C1C2C(CC3C1C(=O)OC3=O)C(=O)OC2=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.7, "product": "C1C2C(CC3C1C(=O)OC3=O)C(=O)OC2=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Into a 5-L separable glass flask equipped with a Dimroth condenser, were charged 450 g of 1,2,4,5-cyclohexanetetracarboxylic acid thus obtained and 4000 g of acetic anhydride, and the inner atmosphere was replaced with nitrogen gas while stirring the contents. The contents were heated to a refluxing temperature of the ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Carboxylic acid.Carboxylic acid | Anhydride.Anhydride | null | C1OCC2CC3COCC3CC12 | C1OCC2CC3COCC3CC12 | HO- | null | null | null | O=C(O)C1CC(C(=O)O)C(C(=O)O)CC1C(=O)O>>O=C1OC(=O)C2CC3C(=O)OC(=O)C3CC12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cf997285b9ea42099c032ff04f577df5 | Nc1ccccc1.O=C(O)c1ccccc1>>c1ccc(Nc2ccccc2)cc1 | C(C)(C)[N-]C(C)C.[Li+].NC1=CC=CC=C1.C[Si](N[Si](C)(C)C)(C)C.[Li].NC1=CC=CC=C1.C(C1=CC=CC=C1)(=O)O.C(C1=CC=CC=C1)(=O)O.C[Si](N[Si](C)(C)C)(C)C.[Li]>>C1(=CC=CC=C1)NC1=CC=CC=C1 | [cH:1]1[cH:2][cH:3][c:4]([NH2:5])[cH:12][cH:13]1.O=C(O)[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[cH:1]1[cH:2][cH:3][c:4]([NH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:12][cH:13]1 | Nc1ccccc1.O=C(O)c1ccccc1 | c1ccc(Nc2ccccc2)cc1 | null | null | O1CCCC1.C(C)#N.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 4459fb8c888ad7824c7447b1a12ec31571c303016262bf3b624feaa352de16d1 | fa64142892e6dfdb381fdd81c9f6becd1fc9340df98b16c99dcdc1b0c3fb2b30 | c1ccc(Nc2ccccc2)cc1 | O-C(=O)-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:4]:[c:5] | null | [] | -78 | CELSIUS | null | null | In Scheme 1, Step A, a 2-(arylamino)-benzoic acid or diphenylamine (3) is prepared from the coupling of a suitable benzoic acid (1) and a suitable aniline (2) in the presence of a strong base, for example, lithium 1,1,1,3,3,3-hexamethyldisilazane (LiHMDS) or lithium diisopropylamide, in a polar aprotic solvent such as ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | O1CCCC1.C(C)#N.CN(C=O)C | -78 | null | Nc1ccccc1.O=C(O)c1ccccc1>O1CCCC1.C(C)#N.CN(C=O)C>c1ccc(Nc2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5e94547ceccb45d0af9b3876b217d010 | C#C[Si](C)(C)C.Nc1ccc(I)cc1F>>C[Si](C)(C)C#Cc1ccc(N)c(F)c1 | FC1=C(N)C=CC(=C1)I.[Si](C)(C)(C)C#C>>FC1=C(N)C=CC(=C1)C#C[Si](C)(C)C | [CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[CH:6].I[c:7]1[cH:8][cH:9][c:10]([NH2:11])[c:12]([F:13])[cH:14]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[c:12]([F:13])[cH:14]1 | C#C[Si](C)(C)C.Nc1ccc(I)cc1F | C[Si](C)(C)C#Cc1ccc(N)c(F)c1 | null | [Cu]I.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | C(C)OCC | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#14:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:10]#[CH;D1;+0:11]>>[C;D1;H3:6]-[#14:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 15 | HOUR | 2-Fluoro-4-iodoaniline (5.00 g, 21.1 mmol), CuI (90 mg, 0.42 mmol), and (Ph3P)2PdCl2 (300 mg, 0.42 mmol) were weighed into a flask which was sealed and flushed with N2. A solution of TMS-acetylene (2.28 g, 23.2 mmol) in TEA (20 mL) was added, then the entire mixture stirred 15 hours at room temperature. The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | [Cu]I.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)OCC | null | 15 | C#C[Si](C)(C)C.Nc1ccc(I)cc1F>[Cu]I.Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.C(C)OCC>C[Si](C)(C)C#Cc1ccc(N)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1af78b468b504952ac05aa866c280e95 | C[Si](C)(C)C#Cc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F>>C[Si](C)(C)C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | [Li+].C[Si](C)(C)[N-][Si](C)(C)C.FC1=C(N)C=CC(=C1)C#C[Si](C)(C)C.FC1=C(C(=O)O)C=CC(=C1F)F>>FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C#C[Si](C)(C)C)F | [CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[c:23]([F:24])[cH:25]1.F[c:12]1[c:13]([C:14](=[O:15])[OH:16])[cH:17][cH:18][c:19]([F:20])[c:21]1[F:22]>>[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][c:7]1[cH:8][cH:9][c:10]([NH:11][c:12]2[c:13]([C:14](=[O:15])[OH:16])[cH:17][cH:18][c:19]([F:20])[... | C[Si](C)(C)C#Cc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F | C[Si](C)(C)C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation primary amine | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccccc2)cc1 | F-[c;H0;D3;+0:1](:[c:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5]):[c:6]):[c:7](-[F;D1;H0:8]):[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[F;D1;H0:8]-[c:7](:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[c:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5]):[c:6] | 59 | [{"value": 59.0, "product": "FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C#C[Si](C)(C)C)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.0, "product": "FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C#C[Si](C)(C)C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 15 | HOUR | A mixture of the product of Step A, 2-fluoro-4-[(trimethylsilyl)ethynyl]aniline (3.85 g, 18.6 mmol) and 2,3,4-trifluorobenzoic acid (3.27 g, 18.6 mmol) was dissolved in dry THF (25 mL). The flask was fitted with a pressure-equalising dropping funnel and the entire apparatus evacuated and flushed with N2. The solution w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HF | C1CCOC1 | -78 | 15 | C[Si](C)(C)C#Cc1ccc(N)c(F)c1.O=C(O)c1ccc(F)c(F)c1F>C1CCOC1>C[Si](C)(C)C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fc919ded7e0b4f518a6fe0d13ab6a378 | C[Si](C)(C)C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1>>C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C#C[Si](C)(C)C)F.C(=O)([O-])[O-].[K+].[K+]>>FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C#C)F | C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[OH:12])[cH:13][cH:14][c:15]([F:16])[c:17]2[F:18])[c:19]([F:20])[cH:21]1>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[c:9]([C:10](=[O:11])[OH:12])[cH:13][cH:14][c:15]([F:16])[c:17]2[F:18])[c:19]([F:20])[cH:21]1 | C[Si](C)(C)C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 | null | null | CO | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | c1ccc(Nc2ccccc2)cc1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3]>>[CH;D1;+0:1]#[C:2]-[c:3] | 99 | [{"value": 99.0, "product": "FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C#C)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.0, "product": "FC=1C(=C(C(=O)O)C=CC1F)NC1=C(C=C(C=C1)C#C)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | The product of Step B, 3,4-difluoro-2-[[2-fluoro-4-(trimethylsilylethynyl)phenyl]amino]benzoic acid (3.99 g, 11.0 mmol), was dissolved in MeOH (200 mL), to which was added K2CO3 (3.03 g, 22.0 mmol). This mixture was stirred at room temperature for 15 hours, then the reaction solvent removed under reduced pressure. The ... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1ccccc1.c1ccccc1 | Other | CO | null | 15 | C[Si](C)(C)C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1>CO>C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1 |
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