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-0387783899c642a8b7eb4ba379bcdf5d | ord-dfebadbfd36b490e8964a788e65992ad | CCOC(=O)CCCCCO.CS(=O)(=O)Cl>>CCOC(=O)CCCCCOS(C)(=O)=O | C(C)N(CC)CC.OCCCCCC(=O)OCC.CS(=O)(=O)Cl>>CS(=O)(=O)OCCCCCC(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].Cl[S:12]([CH3:13])(=[O:14])=[O:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][S:12]([CH3:13])(=[O:14])=[O:15] | CCOC(=O)CCCCCO.CS(=O)(=O)Cl | CCOC(=O)CCCCCOS(C)(=O)=O | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 85.3 | [{"value": 85.0, "product": "CS(=O)(=O)OCCCCCC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.3, "product": "CS(=O)(=O)OCCCCCC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of non-polydispersed ethyl 6-hydroxyhexanoate (50.76 ml, 50.41 g, 227 mmol) in dry dichloromethane (75 ml) was chilled in a ice bath and placed under a nitrogen atmosphere. Triethylamine (34.43 ml, 24.99 g, 247 mmol) was added. A solution of methanesulfonyl chloride (19.15 ml, 28.3 g, 247 mmol) in dry dichlo... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | null | HCl | ClCCl | null | null | CCOC(=O)CCCCCO.CS(=O)(=O)Cl>ClCCl>CCOC(=O)CCCCCOS(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9bba9a86065b4d8483308504bd153486 | CCOC(=O)CCCCCOS(C)(=O)=O.OCCOCCOCCOCCOCCOCCOCc1ccccc1>>CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCc1ccccc1 | CS(=O)(=O)OCCCCCC(=O)OCC.[H-].[Na+].C(C1=CC=CC=C1)OCCOCCOCCOCCOCCOCCO.[H-].[Na+]>>C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCOCC1=CC=CC=C1)=O | CS(=O)(=O)O[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH2:27][CH2:28][O:29][CH2:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][C... | CCOC(=O)CCCCCOS(C)(=O)=O.OCCOCCOCCOCCOCCOCCOCc1ccccc1 | CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCc1ccccc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 5c62be0c00207c22aa0b4ea40c3bc578847f280a3c2710713116f1e5286da21f | f5cafe2a44880b31731a61404bce855c60bfa52affda0d60b208bb5279cadd5b | c1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[C:2]-[C:3] | 44 | [{"value": 44.0, "product": "C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCOCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.8, "product": "C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCOCC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | Sodium hydride (3.225 g or a 60% oil dispersion, 80.6 mmol) was suspended in 80 ml of anhydrous toluene, placed under a nitrogen atmosphere and cooled in an ice bath. A solution of the non-polydispersed alcohol 16 (27.3 g, 73.3 mmol) in 80 ml dry toluene was added to the NaH suspension. The mixture was stirred at 0° C.... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Primary alcohol | Ether | null | null | c1ccccc1 | MsOH.HO- | C1(=CC=CC=C1)C | 0 | null | CCOC(=O)CCCCCOS(C)(=O)=O.OCCOCCOCCOCCOCCOCCOCc1ccccc1>C1(=CC=CC=C1)C>CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-67416f13c9b04edc8abc697d90f711e0 | CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCc1ccccc1>>CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCO | C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCOCC1=CC=CC=C1)=O>>C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCO)=O | c1ccc(C[O:29][CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:... | CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCc1ccccc1 | CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCO | null | [Pd] | C(C)O | Deprotection | Hydroxyl benzyl deprotection | c8a6fd2e05b2d36256c76b73aaf4118f20eb14abce1c0289b554265e30b218aa | 29a81fd08d26edc3da6d72c4958026f5af2119326dc1b4714ee5be1c41835609 | null | [C:1]-[C:2]-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2]-[OH;D1;+0:3] | 79 | [{"value": 79.0, "product": "C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCO)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.9, "product": "C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Non-polydispersed benzyl ether 18 (1.03 g, 2.0 mmol) was dissolved in 25 ml ethanol. To this solution was added 270 mg 10% Pd/C, and the mixture was placed under a hydrogen atmosphere and stirred for four hours, at which time TLC showed the complete disappearance of the starting material. The reaction mixture was filte... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol | c1ccccc1 | null | null | Other | [Pd].C(C)O | null | 4 | CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCc1ccccc1>[Pd].C(C)O>CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-16385851bfdb4201b9822debf3b17ac7 | CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCO.CS(=O)(=O)Cl>>CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCS(C)(=O)=O | C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCO)=O.C(C)N(CC)CC.CS(=O)(=O)Cl>>C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCS(=O)(=O)C)=O | O[CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].Cl[S:29]([CH3:30])(=[O:31])=[O:32]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][CH2:12]... | CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCO.CS(=O)(=O)Cl | CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCS(C)(=O)=O | null | null | ClCCl | Acylation | OtherReaction | 0ac8a603953c98c1814574689e0056190c62616c176b8b4c31c7acd96ef43528 | 7d02e147285bb417922c236d16ce79bf71b54bc3f6dc1c2237422f2069c2cc63 | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].O-[CH2;D2;+0:5]-[C:6]-[#8:7]>>[#8:7]-[C:6]-[CH2;D2;+0:5]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 85.4 | [{"value": 83.0, "product": "C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCS(=O)(=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.4, "product": "C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCS(=O)(=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | MINUTE | The non-polydispersed alcohol 19 (0.835 g, 1.97 mmol) was dissolved in 3.5 ml dry dichloromethane and placed under a nitrogen atmosphere. Triethylamine (0.301 ml, 0.219 g, 2.16 mmol) was added and the mixture was chilled in an ice bath. After two minutes, the methanesulfonyl chloride (0.16 ml, 0.248 g, 2.16 mmol) was a... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Sulfone | null | null | null | HCl | ClCCl | 0 | 0.033333 | CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCO.CS(=O)(=O)Cl>ClCCl>CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCS(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b91745a89bd4417cb01af8e321354d1d | CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCS(C)(=O)=O.COCCOCCO>>CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCCOC | C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCS(=O)(=O)C)=O.[H-].[Na+].COCCOCCO>>C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCOCCOC)=O | CS(=O)(=O)CCO[CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:26][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10... | CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCS(C)(=O)=O.COCCOCCO | CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCCOC | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 6d997269875377ef22a4c0d7efe65e0adbadca96f5ffe8e44c9a72e2d4e677ef | 0ce75b19ae964881255ad90d79aea86c56b1e7de58d067a06f3fccfc3b5cadf6 | null | C-S(=O)(=O)-C-C-O-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:5]-[C:4] | 62.6 | [{"value": 57.0, "product": "C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCOCCOC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.6, "product": "C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCOCCOC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 4 | HOUR | NaH (88 mg of a 60% dispersion in oil, 2.2 mmol) was suspended in anhydrous toluene (3 ml) under N2 and chilled to 0° C. Non-polydispersed diethylene glycol monomethyl ether (0.26 ml, 0.26 g, 2.2 mmol) that had been dried via azeotropic distillation with toluene was added. The reaction mixture was allowed to warm to ro... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol.Sulfone | Ether | null | null | null | HO- | C1(=CC=CC=C1)C | 0 | 4 | CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCS(C)(=O)=O.COCCOCCO>C1(=CC=CC=C1)C>CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCCOC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-70a9072728b24f74a2fb04d768f59dff | CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCCOC>>COCCOCCOCCOCCOCCOCCOCCOCCCCCC(=O)O | C(C)OC(CCCCCOCCOCCOCCOCCOCCOCCOCCOC)=O>>COCCOCCOCCOCCOCCOCCOCCOCCCCCC(=O)O | CC[O:31][C:29]([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])=[O:30]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH... | CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCCOC | COCCOCCOCCOCCOCCOCCOCCOCCCCCC(=O)O | null | null | [OH-].[Na+] | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | null | 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] | 70.3 | [{"value": 62.0, "product": "COCCOCCOCCOCCOCCOCCOCCOCCCCCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.3, "product": "COCCOCCOCCOCCOCCOCCOCCOCCCCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | Non-polydispersed ester 21 (0.25 g, 0.46 mmol) was stirred for 18 hours in 0.71 ml of 1 N NaOH. After 18 hours, the mixture was concentrated in vacuo to remove the alcohol and the residue dissolved in a further 10 ml of water. The aqueous solution was acidified to pH 2 with 2 N HCl and the product was extracted into di... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | null | Other | [OH-].[Na+] | null | 18 | CCOC(=O)CCCCCOCCOCCOCCOCCOCCOCCOCCOC>[OH-].[Na+]>COCCOCCOCCOCCOCCOCCOCCOCCCCCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c57b5f4f796a498980b66acdd117c019 | ClCc1ccccc1.OCCOCCOCCOCCO>>OCCOCCOCCOCCOCc1ccccc1 | C(COCCOCCOCCO)O.[OH-].[Na+].C(C1=CC=CC=C1)Cl>>C(C1=CC=CC=C1)OCCOCCOCCOCCO | Cl[CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1.[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][OH:13]>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | ClCc1ccccc1.OCCOCCOCCOCCO | OCCOCCOCCOCCOCc1ccccc1 | null | null | [Na+].[Cl-] | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 71 | [{"value": 71.0, "product": "C(C1=CC=CC=C1)OCCOCCOCCOCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.9, "product": "C(C1=CC=CC=C1)OCCOCCOCCOCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To the oil of non-polydispersed tetraethylene glycol (19.4 g, 0.10 mol) was added a solution of NaOH (4.0 g in 4.0 mL) and the reaction was stirred for 15 mm. Then benzyl chloride (3.54 mL, 30.8 mmol) was added and the reaction mixture was heated to 100° C. and stirred overnight. The reaction mixture was cooled to room... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1 | HCl | [Na+].[Cl-] | 100 | null | ClCc1ccccc1.OCCOCCOCCOCCO>[Na+].[Cl-]>OCCOCCOCCOCCOCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-746ede52140b4ff6b3a407b25a39a3df | OCCOCCOCCOCCO.OCCOCCOCCOCCOCc1ccccc1>>OCCOCCOCCOCCOCCOCCOCCOCCOCc1ccccc1 | [H-].[Na+].C(COCCOCCOCCO)O.S(C)(=O)(=O)[O-].C(C1=CC=CC=C1)OCCOCCOCCOCCO>>C(C1=CC=CC=C1)OCCOCCOCCOCCOCCOCCOCCOCCO | O[CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][OH:1].[OH:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2... | OCCOCCOCCOCCO.OCCOCCOCCOCCOCc1ccccc1 | OCCOCCOCCOCCOCCOCCOCCOCCOCc1ccccc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Alcohol to ether | 812cd07f4ebd43f56ac542d53752263143ebee112e6268c60a96876bb9ae6b95 | 31a44c623e879cda50fc3ef399266dde4d5f7d364c38209e2960d8959326fbb0 | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[C:5]-[C:4] | 34.5 | [{"value": 34.0, "product": "C(C1=CC=CC=C1)OCCOCCOCCOCCOCCOCCOCCOCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.5, "product": "C(C1=CC=CC=C1)OCCOCCOCCOCCOCCOCCOCCOCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of tetrahydrofuran (140 mL) containing sodium hydride (0.43 g, 18 mmol) was added dropwise a solution of non-polydispersed tetraethylene glycol (3.5 g, 18 mmol) in tetrahydrofuran (10 mL) and the reaction mixture was stirred for 1 h. Then mesylate of non-polydispersed tetraethylene glycol monobenzylether ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Primary alcohol | Ether | null | null | c1ccccc1 | HO- | O1CCCC1 | null | 1 | OCCOCCOCCOCCO.OCCOCCOCCOCCOCc1ccccc1>O1CCCC1>OCCOCCOCCOCCOCCOCCOCCOCCOCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-97ed9791eb8e474da058fdb5e2848beb | OCCOCCOCCO.OCCOCCOCCOCCOCCOCCO>>COCCOCCOCCOCCOCCOCCO | C(COCCOCCOCCOCCOCCO)O.C(=O)(Cl)Cl.C(COCCOCCO)O.C(=O)(Cl)Cl.C1(=CC=CC=C1)C>>COCCOCCOCCOCCOCCOCCO | [OH:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20].OCCOCCOCCO[CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][OH:2]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][OH:20] | OCCOCCOCCO.OCCOCCOCCOCCOCCOCCO | COCCOCCOCCOCCOCCOCCO | null | null | CCOC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 10f901834b998d67af93c14843d4ff9ef83fea029e2d7ebb1a7141118987c94c | d20b223689f1b397d568403780e4ac92290d10a44fac3bd5a5ecc93c0de7d4ca | null | O-C-C-O-C-C-O-C-C-O-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[OH;D1;+0:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[C:8]-[C:7].[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;D1;H3:10] | null | [] | null | null | 2.5 | HOUR | The following description refers to the scheme illustrated in FIG. 10. Non-polydispersed activated hexaethylene glycol monomethyl ether was prepared analogously to that of non-polydispersed triethylene glycol in Example 39 above. A 20% phosgene in toluene solution (35 mL, 6.66 g, 67.4 mmol phosgene) was chilled under a... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary alcohol.Primary alcohol.Primary alcohol | Ether.Ether | null | null | null | HO- | CCOC(=O)C | null | 2.5 | OCCOCCOCCO.OCCOCCOCCOCCOCCOCCO>CCOC(=O)C>COCCOCCOCCOCCOCCOCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c5ed056b08414006a18d1d645c955333 | CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.Cc1[nH][nH]c(=O)c1Cc1ccc(OC(C)C)cc1>>CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | C(C)(C)OC1=CC=C(C=C1)CC=1C(NNC1C)=O.CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)Br)OC(=O)C)OC(=O)C)OC(=O)C>>C(C)(C)OC1=CC=C(C=C1)CC=1C(=NNC1C)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O | Br[C@H:8]1[O:7][C@H:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])[C@@H:37]([O:38][C:39]([CH3:40])=[O:41])[C@H:32]([O:33][C:34]([CH3:35])=[O:36])[C@H:27]1[O:28][C:29]([CH3:30])=[O:31].[O:9]=[c:10]1[nH:11][nH:12][c:13]([CH3:14])[c:15]1[CH2:16][c:17]1[cH:18][cH:19][c:20]([O:21][CH:22]([CH3:23])[CH3:24])[cH:25][cH:26]1>>[CH3:1][C:2... | CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.Cc1[nH][nH]c(=O)c1Cc1ccc(OC(C)C)cc1 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | null | C([O-])([O-])=O.[Ag+2] | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 49b04419fad6ce95036469eff0b0bfaaabc2fb3bd31dcfbbcd47a76a3bff025b | 5cef8b32be1a1b6849554821131ec7ae3bfda59406cde9d9abe4b3a7d689dd3d | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | Br-[C@@H;D3;+0:1](-[#8:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[C:10]-[c:11]1:[c:12](-[C;D1;H3:13]):[#7;a:14]:[nH;D2;+0:15]:[c;H0;D3;+0:16]:1=[O;H0;D1;+0:17]>>[C:10]-[c:11]1:[c:12](-[C;D1;H3:13]):[#7;a:14]:[n;H0;D2;+0:15]:[c;H0;D3;+0:16]:1-[O;H0;D2;+0:17]-[C@H;D3;+0:1](-[#8:2]-[C:3])-[C:4](-[#8:5... | 39 | [{"value": 39.0, "product": "C(C)(C)OC1=CC=C(C=C1)CC=1C(=NNC1C)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 1,2-dihydro-4-[(4-isopropoxyphenyl)methyl]-5-methyl-3H-pyrazol-3-one (46 mg), acetobromo-α-D-glucose (99 mg) and 4A molecular sieves in tetrahydrofuran (3 mL) was added silver carbonate (66 mg), and the mixture was stirred under shading the light at 65° C. overnight. The reaction mixture was purified... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ether | Ether.Ether | C1CCOCC1.c1cn[nH]c1 | C1CCOCC1.c1cn[nH]c1 | C1CCOCC1.c1cn[nH]c1.c1ccccc1 | HBr | C([O-])([O-])=O.[Ag+2].O1CCCC1 | null | null | CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.Cc1[nH][nH]c(=O)c1Cc1ccc(OC(C)C)cc1>C([O-])([O-])=O.[Ag+2].O1CCCC1>CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b562d3e77f564e41b1f17ad26cfc3d50 | CI.COc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C)cc1>>COc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)nn(C)c2C)cc1 | COC1=CC=C(C=C1)CC=1C(=NNC1C)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O.C([O-])([O-])=O.[K+].[K+].IC>>COC1=CC=C(C=C1)CC=1C(=NN(C1C)C)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O | I[CH3:36].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][c:8]2[c:9]([O:10][C@@H:11]3[O:12][C@H:13]([CH2:14][O:15][C:16]([CH3:17])=[O:18])[C@@H:19]([O:20][C:21]([CH3:22])=[O:23])[C@H:24]([O:25][C:26]([CH3:27])=[O:28])[C@H:29]3[O:30][C:31]([CH3:32])=[O:33])[n:34][nH:35][c:37]2[CH3:38])[cH:39][cH:40]1>>[CH3:1][O:2][c:3]1[cH:... | CI.COc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C)cc1 | COc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)nn(C)c2C)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1feb5c3ff035c64f7021c6a0375839863d523e5d8e7a88a1745adbd51ab4e08b | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[nH;D2;+0:7]:1>>[C;D1;H3:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[n;H0;D3;+0:7]:1-[CH3;D1;+0:1] | 21.7 | [{"value": 21.7, "product": "COC1=CC=C(C=C1)CC=1C(=NN(C1C)C)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 8 | HOUR | A suspension of 4-[(4-methoxyphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (18 mg), potassium carbonate (14 mg) and iodomethane (4.7 mg) in acetonitrile (2 mL) was stirred at 75° C. overnight. The reaction mixture was filtered through celite®, and the solvent of the filtrate was r... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cn[nH]c1 | c1cn[nH]c1 | c1ccccc1.C1CCOCC1.c1cn[nH]c1 | HI | C(C)#N | 75 | 8 | CI.COc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C)cc1>C(C)#N>COc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)nn(C)c2C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e33a461d2e6540e4b73193f31070bcce | CI.CSc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C(F)(F)F)cc1>>CSc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)nn(C)c2C(F)(F)F)cc1 | CSC1=CC=C(C=C1)CC=1C(=NNC1C(F)(F)F)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O.C([O-])([O-])=O.[K+].[K+].IC>>CN1N=C(C(=C1C(F)(F)F)CC1=CC=C(C=C1)SC)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O | I[CH3:36].[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][c:8]2[c:9]([O:10][C@@H:11]3[O:12][C@H:13]([CH2:14][O:15][C:16]([CH3:17])=[O:18])[C@@H:19]([O:20][C:21]([CH3:22])=[O:23])[C@H:24]([O:25][C:26]([CH3:27])=[O:28])[C@H:29]3[O:30][C:31]([CH3:32])=[O:33])[n:34][nH:35][c:37]2[C:38]([F:39])([F:40])[F:41])[cH:42][cH:43]1>>[C... | CI.CSc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C(F)(F)F)cc1 | CSc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)nn(C)c2C(F)(F)F)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 1feb5c3ff035c64f7021c6a0375839863d523e5d8e7a88a1745adbd51ab4e08b | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | I-[CH3;D1;+0:1].[F;D1;H0:2]-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[nH;D2;+0:10]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:10]1:[#7;a:9]:[c:8]:[c:7]:[c:6]:1-[C:3](-[F;D1;H0:2])(-[F;D1;H0:4])-[F;D1;H0:5] | 42.4 | [{"value": 42.4, "product": "CN1N=C(C(=C1C(F)(F)F)CC1=CC=C(C=C1)SC)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 75 | CELSIUS | 8 | HOUR | A suspension of 4-[(4-metylthiophenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole (30 mg), potassium carbonate (8.0 mg) and iodomethane (8.2 mg) in tetrahydrofuran (1 mL) was stirred at 75° C. overnight. The reaction mixture was filtered through celite®, and the solvent of the... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cn[nH]c1 | c1cn[nH]c1 | c1ccccc1.C1CCOCC1.c1cn[nH]c1 | HI | O1CCCC1 | 75 | 8 | CI.CSc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C(F)(F)F)cc1>O1CCCC1>CSc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)nn(C)c2C(F)(F)F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d61b8c20f62f4e75b1837978d59d0a91 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O>>Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(OC(C)C)cc1 | C(C)(C)OC1=CC=C(C=C1)CC=1C(=NNC1C)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O.[OH-].[Na+]>>[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NNC(=C1CC1=CC=C(C=C1)OC(C)C)C | CC(=O)[O:11][CH2:10][C@H:9]1[O:8][C@@H:7]([O:6][c:5]2[n:4][nH:3][c:2]([CH3:1])[c:18]2[CH2:19][c:20]2[cH:21][cH:22][c:23]([O:24][CH:25]([CH3:26])[CH3:27])[cH:28][cH:29]2)[C@H:16]([O:17]C(C)=O)[C@@H:14]([O:15]C(C)=O)[C@@H:12]1[O:13]C(C)=O>>[CH3:1][c:2]1[nH:3][n:4][c:5]([O:6][C@@H:7]2[O:8][C@H:9]([CH2:10][OH:11])[C@@H:12]... | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(OC(C)C)cc1 | null | null | C(C)O | Reduction | OtherReaction | f25a9a23a5ab89548ff4c6a5183e7d00920a9005d871a82164b8da27dcb3ee4f | 613f6029949a010495656f96609cb4885878fc82e324c8aa3a03bf565e6d5cf2 | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]1-[#8:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C(-C)=O)-[C:8](-[O;H0;D2;+0:9]-C(-C)=O)-[C:10]-1-[O;H0;D2;+0:11]-C(-C)=O>>[OH;D1;+0:1]-[C:2]-[C:3]1-[#8:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8](-[OH;D1;+0:9])-[C:10]-1-[OH;D1;+0:11] | 90.3 | [{"value": 90.3, "product": "[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NNC(=C1CC1=CC=C(C=C1)OC(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 4-[(4-isopropoxyphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (61 mg) in ethanol (3 mL) was added 1 mol/L aqueous sodium hydroxide solution (0.53 mL), and the mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ester | Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1cn[nH]c1.C1CCOCC1.c1ccccc1 | HO- | C(C)O | null | 2 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O>C(C)O>Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(OC(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-537122eec4594f99b09680e5492ce3db | Cc1ccc(Cc2c(C)[nH][nH]c2=O)cc1>>Cc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1 | CC1=C(C(NN1)=O)CC1=CC=C(C=C1)C.CC1=C(C(=NN1)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O)CC1=CC=C(C=C1)C>>CC1=C(C(=NN1)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O)CC1=CC=C(C=C1)C.[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NNC(=C1CC1=CC=C(C=C1)C)C | [CH3:39][c:40]1[cH:41][cH:42][c:43]([CH2:44][c:45]2[c:46](=[O:47])[nH:59][nH:60][c:61]2[CH3:62])[cH:63][cH:64]1>>[CH3:39][c:40]1[cH:41][cH:42][c:43]([CH2:44][c:45]2[c:46]([O:47][C@@H:48]3[O:49][C@H:50]([CH2:51][OH:52])[C@@H:53]([OH:54])[C@H:55]([OH:56])[C@H:57]3[OH:58])[n:59][nH:60][c:61]2[CH3:62])[cH:63][cH:64]1 | Cc1ccc(Cc2c(C)[nH][nH]c2=O)cc1 | Cc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1 | null | null | null | Functional Group Interconversion | OtherReaction | ead1fc6f6adf9c6d299f2cfdd5a28b72dce9daf92747912a06341759e2e7b8cd | 6f24b6011ab4070dd247a50f72b747bca7d9d29ae512b8f5758535ae9ced16bd | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | [C:1]-[c:2]1:[c:3](-[C;D1;H3:4]):[#7;a:5]:[nH;D2;+0:6]:[c;H0;D3;+0:7]:1=[O;H0;D1;+0:8]>>[#8:9]-[C:10](-[O;H0;D2;+0:8]-[c;H0;D3;+0:7]1:[n;H0;D2;+0:6]:[#7;a:5]:[c:3](-[C;D1;H3:4]):[c:2]:1-[C:1])-[C:11] | null | [] | null | null | null | null | 5-Methyl-4-[(4-methylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole was prepared in a similar manner to that described in Reference Example 17 using 1,2-dihydro-5-methyl-4-[(4-methylphenyl)methyl]-3H-pyrazol-3-one instead of 1,2-dihydro-4-[(4-isopropoxyphenyl)methyl]-5-methyl-3H-pyrazol-3-o... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether.Ether.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | c1cn[nH]c1 | C1CCOCC1.c1cn[nH]c1 | c1ccccc1.C1CCOCC1.c1cn[nH]c1 | Other | null | null | null | Cc1ccc(Cc2c(C)[nH][nH]c2=O)cc1>>Cc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-179e2489aa3a402b93e9d427033a793a | CCc1ccc(Cc2c(C)[nH][nH]c2=O)cc1.CCc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C)cc1>>CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1.CCc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C)cc1 | C(C)C1=CC=C(C=C1)CC=1C(NNC1C)=O.C(C)C1=CC=C(C=C1)CC=1C(=NNC1C)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O>>C(C)C1=CC=C(C=C1)CC=1C(=NNC1C)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O.C(C)C1=CC=C(C=C1)CC=1C(=NNC1C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][c:8]2[c:9](=[O:10])[nH:22][nH:23][c:24]2[CH3:25])[cH:11][cH:27]1.[O:12]=[C:58]([O:57][C@H:56]1[C@H:38]([O:37][c:36]2[c:35]([CH2:34][c:33]3[cH:32][cH:31][c:30]([CH2:29][CH3:28])[cH:66][cH:65]3)[c:63]([CH3:64])[nH:62][n:61]2)[O:39][C@H:40]([CH2:41][O:42][C:43]([CH3:44])=[O:45... | CCc1ccc(Cc2c(C)[nH][nH]c2=O)cc1.CCc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C)cc1 | CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1.CCc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 592adb9d757535711ffe1e347e4e55cc6b2984a3700e5cdc8ea78b2758812a5c | 937ea61182978671c46bd7d19dc6fe5da5cc6e7bc7f356488afe6902ad80b54b | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1.c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | [C:1]-[#8:2]-[C;H0;D3;+0:3](-[C;D1;H3:4])=[O;H0;D1;+0:5].[C:6]-[c:7]1:[c:8]:[c:9]:[c;H0;D3;+0:10](-[C:11]-[c:12]2:[c:13](-[C;D1;H3:14]):[#7;a:15]:[nH;D2;+0:16]:[c;H0;D3;+0:17]:2=[O;H0;D1;+0:18]):[cH;D2;+0:19]:[cH;D2;+0:20]:1>>[C:1]-[#8:2]-[C;H0;D3;+0:3](-[C;D1;H3:4])=[O;D1;H0:21].[C:22]-[C:23]1-[C:24]-[C:25]-[C:26](-[O... | null | [] | null | null | null | null | 4-[(4-Ethylphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole was prepared in a similar manner to that described in Reference Example 17 using 4-[(4-ethylphenyl)methyl]-1,2-dihydro-5-methyl-3H-pyrazol-3-one instead of 1,2-dihydro-4-[(4-isopropoxyphenyl)methyl]-5-methyl-3H-pyrazol-3-one... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester.Ether.Ether.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | c1ccccc1.c1cn[nH]c1 | c1ccccc1.C1CCOCC1.c1cn[nH]c1 | c1ccccc1.C1CCOCC1.c1cn[nH]c1.c1ccccc1.C1CCOCC1.c1cn[nH]c1 | Other | null | null | null | CCc1ccc(Cc2c(C)[nH][nH]c2=O)cc1.CCc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C)cc1>>CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1.CCc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-838e05a218c94742b8a20712003758a3 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.Cc1ccc(Cc2c(C(F)(F)F)[nH][nH]c2=O)cc1>>CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.Cc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C(F)(F)F)cc1 | CC1=CC=C(C=C1)CC=1C(NNC1C(F)(F)F)=O.CC1=CC=C(C=C1)CC=1C(=NNC1C(F)(F)F)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O>>CC1=CC=C(C=C1)CC=1C(=NNC1C(F)(F)F)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O.[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NNC(=C1CC1=CC=C(C=C1)C)C(F)(F)... | [CH3:1][C:2](=[O:3])[O:55][CH2:54][C@H:6]1[O:7][C@@H:8]([O:9][c:10]2[n:11][nH:12][c:13]([C:14]([F:15])([F:16])[F:17])[c:18]2[CH2:19][c:20]2[cH:21][cH:22][c:23]([CH3:24])[cH:25][cH:26]2)[C@H:27]([O:28][C:29]([CH3:30])=[O:31])[C@@H:32]([O:33][C:34]([CH3:35])=[O:36])[C@@H:37]1[O:38][C:39]([CH3:40])=[O:41].[cH:5]1[c:43]([C... | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.Cc1ccc(Cc2c(C(F)(F)F)[nH][nH]c2=O)cc1 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.Cc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C(F)(F)F)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 0b8b5f6db4a34c743cc3167e2ce22fb696d301ae8448ac80920e3a63a1841af4 | 599bf7deebc0c24e008a302dfac22321b5f8821e672c2ca95f7e6500f7a0697c | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1.c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | [C;D1;H3:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5](-[C:6]-[c:7]2:[c:8](-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12]):[#7;a:13]:[nH;D2;+0:14]:[c;H0;D3;+0:15]:2=[O;H0;D1;+0:16]):[cH;D2;+0:17]:[cH;D2;+0:18]:1.[C:19]-[C:20](-[#8:21]-[C:22](-[C;D1;H3:23])=[O;D1;H0:24])-[C@@H;D3;+0:25](-[CH2;D2;+0:26]-[O;H0;D2;+0:27]-[C;H0;D... | null | [] | null | null | null | null | 4-[(4-Methylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole was prepared in a similar manner to that described in Reference Example 28 using 1,2-dihydro-4-[(4-methylphenyl)methyl]-5-trifluoromethyl-3H-pyrazol-3-one instead of 1,2-dihydro-4-[(4-methylthiophenyl)methyl]-5-tri... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Ester.Ether.Ether.Ether.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | C1CCOCC1.c1ccccc1.c1cn[nH]c1 | C1CCOCC1.c1ccccc1.C1CCOCC1.c1cn[nH]c1 | C1CCOCC1.c1cn[nH]c1.c1ccccc1.c1ccccc1.C1CCOCC1.c1cn[nH]c1 | Other | null | null | null | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.Cc1ccc(Cc2c(C(F)(F)F)[nH][nH]c2=O)cc1>>CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.Cc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C(F)(F)F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c7ae01a6659f4969a653293054d6e2c5 | CCc1ccc(Cc2c(C(F)(F)F)[nH][nH]c2=O)cc1.CCc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C(F)(F)F)cc1>>CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C(F)(F)F)cc1.CCc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C(F)(F)F)cc1 | C(C)C1=CC=C(C=C1)CC=1C(NNC1C(F)(F)F)=O.C(C)C1=CC=C(C=C1)CC=1C(=NNC1C(F)(F)F)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O>>C(C)C1=CC=C(C=C1)CC=1C(=NNC1C(F)(F)F)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O.C(C)C1=CC=C(C=C1)CC=1C(=NNC1C(F)(F)F)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[... | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][c:8]2[c:11](=[O:10])[nH:22][nH:23][c:24]2[C:25]([F:26])([F:27])[F:28])[cH:29][cH:30]1.[O:12]=[C:51]([O:50][C@@H:49]1[C@@H:43]([CH2:44][O:45][C:46]([CH3:47])=[O:48])[O:42][C@@H:41]([O:40][c:39]2[c:38]([CH2:37][c:36]3[cH:35][cH:34][c:33]([CH2:32][CH3:31])[cH:72][cH:71]3)[c:66... | CCc1ccc(Cc2c(C(F)(F)F)[nH][nH]c2=O)cc1.CCc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C(F)(F)F)cc1 | CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C(F)(F)F)cc1.CCc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C(F)(F)F)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 588966879a4e0a248367cf6537a49ab469bbb39132939017556322288c651d3c | 937ea61182978671c46bd7d19dc6fe5da5cc6e7bc7f356488afe6902ad80b54b | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1.c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | [C:1]-[#8:2]-[C;H0;D3;+0:3](-[C;D1;H3:4])=[O;H0;D1;+0:5].[F;D1;H0:6]-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[c:10]1:[#7;a:11]:[nH;D2;+0:12]:[c;H0;D3;+0:13](=[O;H0;D1;+0:14]):[c;H0;D3;+0:15]:1-[C:16]-[c:17]>>[C:1]-[#8:2]-[C;H0;D3;+0:3](-[C;D1;H3:4])=[O;D1;H0:18].[C:19]-[C:20]1-[C:21]-[C:22]-[C:23](-[O;D1;H1:24])-[C@H;D3;+0:1... | null | [] | null | null | null | null | 4-[(4-Ethylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole was prepared in a similar manner to that described in Reference Example 28 using 4-[(4-ethylphenyl)methyl]-1,2-dihydro-5-trifluoromethyl-3H-pyrazol-3-one instead of 1,2-dihydro-4-[(4-methylthiophenyl)methyl]-5-trifl... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester.Ether.Ether.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | c1cn[nH]c1 | C1CCOCC1.c1cn[nH]c1 | c1ccccc1.C1CCOCC1.c1cn[nH]c1.c1ccccc1.C1CCOCC1.c1cn[nH]c1 | Other | null | null | null | CCc1ccc(Cc2c(C(F)(F)F)[nH][nH]c2=O)cc1.CCc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C(F)(F)F)cc1>>CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C(F)(F)F)cc1.CCc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C(F)(F)F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-45f7121aed9348e4b12295753c2a5f23 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(C(C)C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.CC(C)c1ccc(Cc2c(C(F)(F)F)[nH][nH]c2=O)cc1>>CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(C(C)C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.CC(C)c1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C(F... | C(C)(C)C1=CC=C(C=C1)CC=1C(NNC1C(F)(F)F)=O.C(C)(C)C1=CC=C(C=C1)CC=1C(=NNC1C(F)(F)F)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O>>C(C)(C)C1=CC=C(C=C1)CC=1C(=NNC1C(F)(F)F)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O.[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NNC(=C1CC1=C... | [CH3:1][C:2](=[O:3])[O:59][CH2:58][C@H:6]1[O:7][C@@H:8]([O:9][c:10]2[n:11][nH:12][c:13]([C:14]([F:15])([F:16])[F:17])[c:18]2[CH2:19][c:20]2[cH:21][cH:22][c:23]([CH:24]([CH3:5])[CH3:25])[cH:27][cH:28]2)[C@H:29]([O:30][C:31]([CH3:32])=[O:33])[C@@H:34]([O:35][C:36]([CH3:37])=[O:38])[C@@H:39]1[O:40][C:41](=[O:4])[CH3:42].[... | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(C(C)C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.CC(C)c1ccc(Cc2c(C(F)(F)F)[nH][nH]c2=O)cc1 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(C(C)C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.CC(C)c1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C(F)(F)F)cc1 | null | null | null | Acylation | OtherReaction | 42b311b4525c90cc17b416d07ff3eab9ae67d2b5d627eeef62e3abdf7dafcd1a | 5c0fb37557b0c07a62063fc52ad33794ddafbacbff284feaf8591e504c1746af | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1.c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | [C;D1;H3:1]-[CH;D3;+0:2](-[CH3;D1;+0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8](-[#8:9]-[C;H0;D3;+0:10](-[C;D1;H3:11])=[O;H0;D1;+0:12])-[C@@H;D3;+0:13](-[CH2;D2;+0:14]-[O;H0;D2;+0:15]-[C;H0;D3;+0:16](-[C;D1;H3:17])=[O;D1;H0:18])-[#8:19]-[C:20].[C:21]-[c:22]1:[c:23](-[C:24](-[F;D1;H0:25])(-[F;D1;H0:26])-[F;D1;H0:27]):[#7;a:28]... | null | [] | null | null | null | null | 4-[(4-Isopropylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole was prepared in a similar manner to that described in Reference Example 28 using 1,2-dihydro-4-[(4-isopropylphenyl)methyl]-5-trifluoromethyl-3H-pyrazol-3-one instead of 1,2-dihydro-4-[(4-methylthiophenyl)methyl]... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether | Ester.Ester.Ether.Ether.Ether.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | C1CCOCC1.c1cn[nH]c1 | C1CCOCC1.C1CCOCC1.c1cn[nH]c1 | C1CCOCC1.c1cn[nH]c1.c1ccccc1.c1ccccc1.C1CCOCC1.c1cn[nH]c1 | Other | null | null | null | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(C(C)C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.CC(C)c1ccc(Cc2c(C(F)(F)F)[nH][nH]c2=O)cc1>>CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(C(C)C)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.CC(C)c1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C(F... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0f09344767634b0ea9b95aea6d8b3c62 | O=c1[nH][nH]c(C(F)(F)F)c1Cc1ccc(Cl)cc1>>OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(Cl)cc2)[C@H](O)[C@@H](O)[C@@H]1O | ClC1=CC=C(C=C1)CC=1C(NNC1C(F)(F)F)=O.ClC1=CC=C(C=C1)CC=1C(=NNC1C(F)(F)F)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O>>ClC1=CC=C(C=C1)CC=1C(=NNC1C(F)(F)F)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O.ClC1=CC=C(C=C1)CC=1C(=NNC1C(F)(F)F)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)... | [O:47]=[c:48]1[nH:49][nH:50][c:51]([C:52]([F:53])([F:54])[F:55])[c:56]1[CH2:57][c:58]1[cH:59][cH:60][c:61]([Cl:62])[cH:63][cH:64]1>>[OH:42][CH2:43][C@H:44]1[O:45][C@@H:46]([O:47][c:48]2[n:49][nH:50][c:51]([C:52]([F:53])([F:54])[F:55])[c:56]2[CH2:57][c:58]2[cH:59][cH:60][c:61]([Cl:62])[cH:63][cH:64]2)[C@H:65]([OH:66])[C... | O=c1[nH][nH]c(C(F)(F)F)c1Cc1ccc(Cl)cc1 | OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(Cl)cc2)[C@H](O)[C@@H](O)[C@@H]1O | null | null | null | Functional Group Interconversion | OtherReaction | ead1fc6f6adf9c6d299f2cfdd5a28b72dce9daf92747912a06341759e2e7b8cd | 6f24b6011ab4070dd247a50f72b747bca7d9d29ae512b8f5758535ae9ced16bd | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | [C:1]-[c:2]1:[c:3](-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7]):[#7;a:8]:[nH;D2;+0:9]:[c;H0;D3;+0:10]:1=[O;H0;D1;+0:11]>>[#8:12]-[C:13](-[O;H0;D2;+0:11]-[c;H0;D3;+0:10]1:[n;H0;D2;+0:9]:[#7;a:8]:[c:3](-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7]):[c:2]:1-[C:1])-[C:14] | null | [] | null | null | null | null | 4-[(4-Chlorophenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-trifluoromethyl-1H-pyrazole was prepared in a similar manner to that described in Reference Example 28 using 4-[(4-chlorophenyl)methyl]-1,2-dihydro-5-trifluoromethyl-3H-pyrazol-3-one instead of 1,2-dihydro-4-[(4-methylthiophenyl)methyl]-5-tri... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether.Ether.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | c1cn[nH]c1 | C1CCOCC1.c1cn[nH]c1 | C1CCOCC1.c1cn[nH]c1.c1ccccc1 | Other | null | null | null | O=c1[nH][nH]c(C(F)(F)F)c1Cc1ccc(Cl)cc1>>OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(Cl)cc2)[C@H](O)[C@@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ffb7d161865847f1bf650ced4312ad02 | CCCI.Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(OC(C)C)cc1>>CCCn1nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(Cc2ccc(OC(C)C)cc2)c1C | O.[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NNC(=C1CC1=CC=C(C=C1)OC(C)C)C.C([O-])([O-])=O.[Cs+].[Cs+].ICCC>>[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NN(C(=C1CC1=CC=C(C=C1)OC(C)C)C)CCC | I[CH2:3][CH2:2][CH3:1].[nH:4]1[n:5][c:6]([O:7][C@@H:8]2[O:9][C@H:10]([CH2:11][OH:12])[C@@H:13]([OH:14])[C@H:15]([OH:16])[C@H:17]2[OH:18])[c:19]([CH2:20][c:21]2[cH:22][cH:23][c:24]([O:25][CH:26]([CH3:27])[CH3:28])[cH:29][cH:30]2)[c:31]1[CH3:32]>>[CH3:1][CH2:2][CH2:3][n:4]1[n:5][c:6]([O:7][C@@H:8]2[O:9][C@H:10]([CH2:11][... | CCCI.Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(OC(C)C)cc1 | CCCn1nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(Cc2ccc(OC(C)C)cc2)c1C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 31849359320dc3760d1a762ce95f120a544970fcb32b476aacf584ef81779a29 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | I-[CH2;D2;+0:1]-[C:2]-[C;D1;H3:3].[C;D1;H3:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[C;D1;H3:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1-[C;D1;H3:4] | null | [] | null | null | 8 | HOUR | To a suspension of 3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole (50 mg) and cesium carbonate (0.20 g) in N,N-dimethylformamide (1 mL) was added 1-iodopropane (0.036 mL) at 50° C., and the mixture was stirred overnight. Water was added to the reaction mixture, and the resulting mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.C1CCOCC1.c1ccccc1 | HI | CN(C=O)C | null | 8 | CCCI.Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(OC(C)C)cc1>CN(C=O)C>CCCn1nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(Cc2ccc(OC(C)C)cc2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b2dea7738eaa4cfb935cd2bb2dc8e01e | CCI.COc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1>>CCn1nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(Cc2ccc(OC)cc2)c1C | [C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NNC(=C1CC1=CC=C(C=C1)OC)C.ICC>>C(C)N1N=C(C(=C1C)CC1=CC=C(C=C1)OC)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO | I[CH2:2][CH3:1].[nH:3]1[n:4][c:5]([O:6][C@@H:7]2[O:8][C@H:9]([CH2:10][OH:11])[C@@H:12]([OH:13])[C@H:14]([OH:15])[C@H:16]2[OH:17])[c:18]([CH2:19][c:20]2[cH:21][cH:22][c:23]([O:24][CH3:25])[cH:26][cH:27]2)[c:28]1[CH3:29]>>[CH3:1][CH2:2][n:3]1[n:4][c:5]([O:6][C@@H:7]2[O:8][C@H:9]([CH2:10][OH:11])[C@@H:12]([OH:13])[C@H:14]... | CCI.COc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1 | CCn1nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(Cc2ccc(OC)cc2)c1C | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 31849359320dc3760d1a762ce95f120a544970fcb32b476aacf584ef81779a29 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[C;D1;H3:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[nH;D2;+0:8]:1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[#7;a:7]:[c:6]:[c:5]:[c:4]:1-[C;D1;H3:3] | null | [] | null | null | null | null | The title compound was prepared in a similar manner to that described in Reference Example 63 using 3-(β-D-glucopyranosyloxy)-4-[(4-methoxyphenyl)methyl]-5-methyl-1H-pyrazole instead of 3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole and using iodoethane instead of 1-iodpropane.
Conditions... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.C1CCOCC1.c1ccccc1 | HI | null | null | null | CCI.COc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1>>CCn1nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(Cc2ccc(OC)cc2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-05a6febe076c439e80579d81cbc982c3 | CCI.CCOc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1>>CCOc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CC)c2C)cc1 | C(C)OC1=CC=C(C=C1)CC=1C(=NNC1C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO.ICC>>C(C)N1N=C(C(=C1C)CC1=CC=C(C=C1)OCC)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO | I[CH2:25][CH3:26].[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][c:9]2[c:10]([O:11][C@@H:12]3[O:13][C@H:14]([CH2:15][OH:16])[C@@H:17]([OH:18])[C@H:19]([OH:20])[C@H:21]3[OH:22])[n:23][nH:24][c:27]2[CH3:28])[cH:29][cH:30]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][c:9]2[c:10]([O:11][C@@H:12]3[O:13][C@H:14](... | CCI.CCOc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1 | CCOc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CC)c2C)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 31849359320dc3760d1a762ce95f120a544970fcb32b476aacf584ef81779a29 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[C;D1;H3:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[nH;D2;+0:8]:1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[#7;a:7]:[c:6]:[c:5]:[c:4]:1-[C;D1;H3:3] | null | [] | null | null | null | null | The title compound was prepared in a similar manner to that described in Reference Example 63 using 4-[(4-ethoxyphenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methyl-1H-pyrazole instead of 3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole and using iodoethane instead of 1-iodopropane.
Conditions... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cn[nH]c1 | c1cn[nH]c1 | c1ccccc1.C1CCOCC1.c1cn[nH]c1 | HI | null | null | null | CCI.CCOc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1>>CCOc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CC)c2C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-19f8ee4ff22a4d6a8da87a5c1406b98c | CCI.CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1>>CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CC)c2C)cc1 | C(C)C1=CC=C(C=C1)CC=1C(=NNC1C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO.ICC>>C(C)N1N=C(C(=C1C)CC1=CC=C(C=C1)CC)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO | I[CH2:24][CH3:25].[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][c:8]2[c:9]([O:10][C@@H:11]3[O:12][C@H:13]([CH2:14][OH:15])[C@@H:16]([OH:17])[C@H:18]([OH:19])[C@H:20]3[OH:21])[n:22][nH:23][c:26]2[CH3:27])[cH:28][cH:29]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][c:8]2[c:9]([O:10][C@@H:11]3[O:12][C@H:13]([CH2:14][OH:... | CCI.CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1 | CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CC)c2C)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 31849359320dc3760d1a762ce95f120a544970fcb32b476aacf584ef81779a29 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[C;D1;H3:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[nH;D2;+0:8]:1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[#7;a:7]:[c:6]:[c:5]:[c:4]:1-[C;D1;H3:3] | null | [] | null | null | null | null | The title compound was prepared in a similar manner to that described in Reference Example 63 using 4-[(4-ethylphenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methyl-1H-pyrazole instead of 3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole and using iodoethane instead of 1-iodopropane.
Conditions:... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cn[nH]c1 | c1cn[nH]c1 | c1ccccc1.C1CCOCC1.c1cn[nH]c1 | HI | null | null | null | CCI.CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1>>CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CC)c2C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3ed1aca0a08245a8b5c6dfa4d562e9ee | CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.CCSc1ccc(Cc2c(C)[nH][nH]c2=O)cc1>>CCSc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C)cc1 | C(C)SC1=CC=C(C=C1)CC=1C(NNC1C)=O.CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)Br)OC(=O)C)OC(=O)C)OC(=O)C>>C(C)SC1=CC=C(C=C1)CC=1C(=NNC1C)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O | Br[C@H:12]1[O:13][C@H:14]([CH2:15][O:16][C:17]([CH3:18])=[O:19])[C@@H:20]([O:21][C:22]([CH3:23])=[O:24])[C@H:25]([O:26][C:27]([CH3:28])=[O:29])[C@H:30]1[O:31][C:32]([CH3:33])=[O:34].[CH3:1][CH2:2][S:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][c:9]2[c:10](=[O:11])[nH:35][nH:36][c:37]2[CH3:38])[cH:39][cH:40]1>>[CH3:1][CH2:2][S:3][... | CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.CCSc1ccc(Cc2c(C)[nH][nH]c2=O)cc1 | CCSc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C)cc1 | null | C([O-])([O-])=O.[Ag+2] | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 49b04419fad6ce95036469eff0b0bfaaabc2fb3bd31dcfbbcd47a76a3bff025b | 5cef8b32be1a1b6849554821131ec7ae3bfda59406cde9d9abe4b3a7d689dd3d | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | Br-[C@@H;D3;+0:1](-[#8:2]-[C:3])-[C:4](-[#8:5]-[C:6](-[C;D1;H3:7])=[O;D1;H0:8])-[C:9].[C:10]-[c:11]1:[c:12](-[C;D1;H3:13]):[#7;a:14]:[nH;D2;+0:15]:[c;H0;D3;+0:16]:1=[O;H0;D1;+0:17]>>[C:3]-[#8:2]-[C@@H;D3;+0:1](-[O;H0;D2;+0:17]-[c;H0;D3;+0:16]1:[n;H0;D2;+0:15]:[#7;a:14]:[c:12](-[C;D1;H3:13]):[c:11]:1-[C:10])-[C:4](-[#8:... | 37.6 | [{"value": 37.6, "product": "C(C)SC1=CC=C(C=C1)CC=1C(=NNC1C)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 4-[(4-ethylthiophenyl)methyl]-1,2-dihydro-5-methyl-3H-pyrazol-3-one (1.6 g) and acetobromo-α-D-glucose (2.9 g) in tetrahydrofuran (30 mL) was added silver carbonate (2.1 g), and the mixture was stirred under shading the light at 60° C. overnight. The reaction mixture was purified by column chromatogr... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ether | Ether.Ether | C1CCOCC1.c1cn[nH]c1 | C1CCOCC1.c1cn[nH]c1 | c1ccccc1.C1CCOCC1.c1cn[nH]c1 | HBr | C([O-])([O-])=O.[Ag+2].O1CCCC1 | null | null | CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.CCSc1ccc(Cc2c(C)[nH][nH]c2=O)cc1>C([O-])([O-])=O.[Ag+2].O1CCCC1>CCSc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5c62563cce7147e181ec6bb887941a7f | CCSc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C)cc1>>CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1 | C(C)SC1=CC=C(C=C1)CC=1C(=NNC1C)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O.C[O-].[Na+]>>C(C)SC1=CC=C(C=C1)CC=1C(=NNC1C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO | CC(=O)[O:16][CH2:15][C@H:14]1[O:13][C@@H:12]([O:11][c:10]2[c:9]([CH2:8][c:7]3[cH:6][cH:5][c:4]([S:3][CH2:2][CH3:1])[cH:28][cH:27]3)[c:25]([CH3:26])[nH:24][n:23]2)[C@H:21]([O:22]C(C)=O)[C@@H:19]([O:20]C(C)=O)[C@@H:17]1[O:18]C(C)=O>>[CH3:1][CH2:2][S:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][c:9]2[c:10]([O:11][C@@H:12]3[O:13][C@H... | CCSc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C)cc1 | CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1 | null | null | CO | Reduction | OtherReaction | f25a9a23a5ab89548ff4c6a5183e7d00920a9005d871a82164b8da27dcb3ee4f | 613f6029949a010495656f96609cb4885878fc82e324c8aa3a03bf565e6d5cf2 | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]1-[#8:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C(-C)=O)-[C:8](-[O;H0;D2;+0:9]-C(-C)=O)-[C:10]-1-[O;H0;D2;+0:11]-C(-C)=O>>[OH;D1;+0:1]-[C:2]-[C:3]1-[#8:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8](-[OH;D1;+0:9])-[C:10]-1-[OH;D1;+0:11] | 94.3 | [{"value": 94.3, "product": "C(C)SC1=CC=C(C=C1)CC=1C(=NNC1C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 4-[(4-ethylthiophenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (1.3 g) in methanol (10 mL) was added sodium methoxide (28% methanol solution, 0.13 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pr... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ester | Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1ccccc1.C1CCOCC1.c1cn[nH]c1 | HO- | CO | null | 1 | CCSc1ccc(Cc2c(O[C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]3OC(C)=O)n[nH]c2C)cc1>CO>CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-98f3503a6a674d06900034c5fded6da5 | CCOC(=O)Cl.Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C(=O)OCc1ccccc1>>CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(=O)OCc3ccccc3)c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O | O.O.C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(C1=CC=CC=C1)OC(=O)N1N=C(C(=C1C)CC1=CC=C(C=C1)OC(C)C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO.ClC(=O)OCC>>C(C1=CC=CC=C1)OC(=O)N1N=C(C(=C1C)CC1=CC=C(C=C1)OC(C)C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)COC(=O)OCC | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:6][CH2:7][C@H:8]1[O:9][C@@H:10]([O:11][c:12]2[n:13][n:14]([C:15](=[O:16])[O:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[c:25]([CH3:26])[c:27]2[CH2:28][c:29]2[cH:30][cH:31][c:32]([O:33][CH:34]([CH3:35])[CH3:36])[cH:37][cH:38]2)[C@H:39]([OH:40])[C@@H:41]([OH:42])[C@@H:43... | CCOC(=O)Cl.Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C(=O)OCc1ccccc1 | CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(=O)OCc3ccccc3)c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O | null | null | CC1=NC(=CC(=C1)C)C | Acylation | Schotten-Baumann to ester | ab2604cac7a0887c37303ad0fec59fb6a84cf40820c840730a9f7f5636dcc83e | 7ed0ec8c4c25c8af523f531911c9dd0a60119de4cab841f882ce9a65c39be54c | O=C(OCc1ccccc1)n1cc(Cc2ccccc2)c(O[C@H]2CCCCO2)n1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | null | [] | null | null | 1 | DAY | To a solution of 1-(benzyloxycarbonyl)-3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methylpyrazole (0.20 g) in 2,4,6-trimethylpyridine (4 mL) was added ethyl chloroformate (0.092 mL), and the mixture was stirred at room temperature for 1 day. To the reaction mixture were added water and citric acid monohy... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary alcohol | Carbonic Ester | null | null | C1CCOCC1.c1cn[nH]c1.c1ccccc1.c1ccccc1 | HCl | CC1=NC(=CC(=C1)C)C | null | 24 | CCOC(=O)Cl.Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C(=O)OCc1ccccc1>CC1=NC(=CC(=C1)C)C>CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(=O)OCc3ccccc3)c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b17bdad534cf48f2a7bb48b047be9ec0 | CCOC(=O)Cl.Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C(C)C>>CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(C)C)c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O | O.C(CC(O)(C(=O)O)CC(=O)O)(=O)O.O.[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NN(C(=C1CC1=CC=C(C=C1)OC(C)C)C)C(C)C.ClC(=O)OCC>>C(C)OC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC1=NN(C(=C1CC1=CC=C(C=C1)OC(C)C)C)C(C)C)O)O)O | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:6][CH2:7][C@H:8]1[O:9][C@@H:10]([O:11][c:12]2[n:13][n:14]([CH:15]([CH3:16])[CH3:17])[c:18]([CH3:19])[c:20]2[CH2:21][c:22]2[cH:23][cH:24][c:25]([O:26][CH:27]([CH3:28])[CH3:29])[cH:30][cH:31]2)[C@H:32]([OH:33])[C@@H:34]([OH:35])[C@@H:36]1[OH:37]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[O:6... | CCOC(=O)Cl.Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C(C)C | CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(C)C)c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O | null | null | CC1=NC(=CC(=C1)C)C | Acylation | Schotten-Baumann to ester | ab2604cac7a0887c37303ad0fec59fb6a84cf40820c840730a9f7f5636dcc83e | 7ed0ec8c4c25c8af523f531911c9dd0a60119de4cab841f882ce9a65c39be54c | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | 72.4 | [{"value": 72.4, "product": "C(C)OC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC1=NN(C(=C1CC1=CC=C(C=C1)OC(C)C)C)C(C)C)O)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-1-isopropyl-5-methylpyrazole (0.10 g) in 2,4,6-trimethylpyridine (1 mL) was added ethyl chloroformate (0.072 g), and the mixture was stirred at room temperature overnight. To the reaction mixture were added citric acid monohydrate (3.3 g) and wat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary alcohol | Carbonic Ester | null | null | C1CCOCC1.c1cn[nH]c1.c1ccccc1 | HCl | CC1=NC(=CC(=C1)C)C | null | 8 | CCOC(=O)Cl.Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C(C)C>CC1=NC(=CC(=C1)C)C>CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(C)C)c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9fb0be25a7f347229a8718714c82051f | CCC(=O)Cl.Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C(C)C>>CCC(=O)OC[C@H]1O[C@@H](Oc2nn(C(C)C)c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O | O.C(CC(O)(C(=O)O)CC(=O)O)(=O)O.O.[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NN(C(=C1CC1=CC=C(C=C1)OC(C)C)C)C(C)C.C(CC)(=O)Cl>>C(C)(C)OC1=CC=C(C=C1)CC=1C(=NN(C1C)C(C)C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)COC(CC)=O | Cl[C:3]([CH2:2][CH3:1])=[O:4].[OH:5][CH2:6][C@H:7]1[O:8][C@@H:9]([O:10][c:11]2[n:12][n:13]([CH:14]([CH3:15])[CH3:16])[c:17]([CH3:18])[c:19]2[CH2:20][c:21]2[cH:22][cH:23][c:24]([O:25][CH:26]([CH3:27])[CH3:28])[cH:29][cH:30]2)[C@H:31]([OH:32])[C@@H:33]([OH:34])[C@@H:35]1[OH:36]>>[CH3:1][CH2:2][C:3](=[O:4])[O:5][CH2:6][C@... | CCC(=O)Cl.Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C(C)C | CCC(=O)OC[C@H]1O[C@@H](Oc2nn(C(C)C)c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O | null | null | CC1=NC(=CC(=C1)C)C | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4] | 65.8 | [{"value": 65.8, "product": "C(C)(C)OC1=CC=C(C=C1)CC=1C(=NN(C1C)C(C)C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)COC(CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a solution of 3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-1-isopropyl-5-methylpyrazole (0.10 g) in 2,4,6-trimethylpyridine (1 mL) was added propionyl chloride (0.072 g) at 0° C., and the mixture was stirred for 5 hours. To the reaction mixture were added citric acid monohydrate (3.3 g) and water, and th... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | C1CCOCC1.c1cn[nH]c1.c1ccccc1 | HCl | CC1=NC(=CC(=C1)C)C | null | 5 | CCC(=O)Cl.Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C(C)C>CC1=NC(=CC(=C1)C)C>CCC(=O)OC[C@H]1O[C@@H](Oc2nn(C(C)C)c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ecce5c467964454bbe231535179e1e69 | CCOC(=O)Cl.CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1.O=C(O)CC(O)(CC(=O)O)C(=O)O>>CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(=O)OCC)c(C)c2Cc2ccc(SCC)cc2)[C@H](O)[C@@H](O)[C@@H]1O | C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(C)SC1=CC=C(C=C1)CC=1C(=NNC1C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO.ClC(=O)OCC.CC1=NC(=CC(=C1)C)C>>C(C)OC(=O)N1N=C(C(=C1C)CC1=CC=C(C=C1)SCC)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)COC(=O)OCC | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:6][CH2:7][C@H:8]1[O:9][C@@H:10]([O:11][c:12]2[n:13][nH:14][c:20]([CH3:21])[c:22]2[CH2:23][c:24]2[cH:25][cH:26][c:27]([S:28][CH2:29][CH3:30])[cH:31][cH:32]2)[C@H:33]([OH:34])[C@@H:35]([OH:36])[C@@H:37]1[OH:38].O=C(O)CC(O)([C:15](=[O:16])[OH:17])[CH2:19][C:18](=O)O>>[CH3:1][CH2:2][O... | CCOC(=O)Cl.CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1.O=C(O)CC(O)(CC(=O)O)C(=O)O | CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(=O)OCC)c(C)c2Cc2ccc(SCC)cc2)[C@H](O)[C@@H](O)[C@@H]1O | null | null | null | Acylation | OtherReaction | 25ac7076f220199fa9802968180efa413e01911e390f776612160eaa82a53ea1 | 6bdfdcb713015be6a43be797a0fe1781e53e91e3d5184a1b120701f9dfb0ecd5 | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].O-C(=O)-C-C(-O)(-[CH2;D2;+0:5]-[C;H0;D3;+0:6](-O)=O)-[C;H0;D3;+0:7](=[O;D1;H0:8])-[OH;D1;+0:9].[#8:10]-[C:11]-[C:12]-[OH;D1;+0:13].[C;D1;H3:14]-[c:15]1:[c:16]:[c:17]:[#7;a:18]:[nH;D2;+0:19]:1>>[#8:10]-[C:11]-[C:12]-[O;H0;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C... | null | [] | null | null | 8 | HOUR | To a solution of 4-[(4-ethylthiophenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methyl-1H-pyrazole (0.03 g) in 2,4,6-trimethylpyridine (0.5 mL) was added ethyl chloroformate (0.021 mL), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 10% aqueous citric acid solution, and the resu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Carboxylic acid.Carboxylic acid.Ether.Primary alcohol.Tertiary alcohol | Carbonic Ester.Ether | c1cn[nH]c1 | c1cn[nH]c1 | C1CCOCC1.c1cn[nH]c1.c1ccccc1 | HCl | null | null | 8 | CCOC(=O)Cl.CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1.O=C(O)CC(O)(CC(=O)O)C(=O)O>>CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(=O)OCC)c(C)c2Cc2ccc(SCC)cc2)[C@H](O)[C@@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7b901fc15a6e4f8abc6c1204b5292bcc | CC(=O)OC(C)=O.CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1>>CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(C(C)=O)c2C)cc1 | C(C)SC1=CC=C(C=C1)CC=1C(=NNC1C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO.C(C)(=O)O.C(C)(=O)OC(C)=O>>C(C)(=O)N1N=C(C(=C1C)CC1=CC=C(C=C1)SCC)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO | CC(=O)O[C:25]([CH3:26])=[O:27].[CH3:1][CH2:2][S:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][c:9]2[c:10]([O:11][C@@H:12]3[O:13][C@H:14]([CH2:15][OH:16])[C@@H:17]([OH:18])[C@H:19]([OH:20])[C@H:21]3[OH:22])[n:23][nH:24][c:28]2[CH3:29])[cH:30][cH:31]1>>[CH3:1][CH2:2][S:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][c:9]2[c:10]([O:11][C@@H:12]3[O... | CC(=O)OC(C)=O.CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1 | CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(C(C)=O)c2C)cc1 | null | null | O1CCCC1 | Acylation | Ester with secondary amine to amide | 56aaf2cf99268e392c632e4472afccfbd54d38cd1eeb15e5e23759d356a361ff | 93289da630dbaf2d9339c4212dcd342dfbcc29df4e79a63418a0fd9f589abdc1 | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C;D1;H3:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[n;H0;D3;+0:9]1:[#7;a:8]:[c:7]:[c:6]:[c:5]:1-[C;D1;H3:4] | null | [] | null | null | 8 | HOUR | To a solution of 4-[(4-ethylthiophenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methyl-1H-pyrazole (0.41 g) in tetrahydrofuran (10 mL) were added acetic acid (0.11 mL) and acetic anhydride (0.18 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | null | c1cn[nH]c1 | c1cn[nH]c1 | c1ccccc1.C1CCOCC1.c1cn[nH]c1 | HO- | O1CCCC1 | null | 8 | CC(=O)OC(C)=O.CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1>O1CCCC1>CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(C(C)=O)c2C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e282bc156d3b4ff5858b7476742a21ad | CCOC(=O)Cl.CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(C(C)=O)c2C)cc1>>CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(C)=O)c(C)c2Cc2ccc(SCC)cc2)[C@H](O)[C@@H](O)[C@@H]1O | C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(C)(=O)N1N=C(C(=C1C)CC1=CC=C(C=C1)SCC)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO.ClC(=O)OCC>>C(C)(=O)N1N=C(C(=C1C)CC1=CC=C(C=C1)SCC)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)COC(=O)OCC | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:6][CH2:7][C@H:8]1[O:9][C@@H:10]([O:11][c:12]2[n:13][n:14]([C:15]([CH3:16])=[O:17])[c:18]([CH3:19])[c:20]2[CH2:21][c:22]2[cH:23][cH:24][c:25]([S:26][CH2:27][CH3:28])[cH:29][cH:30]2)[C@H:31]([OH:32])[C@@H:33]([OH:34])[C@@H:35]1[OH:36]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[O:6][CH2:7][C@... | CCOC(=O)Cl.CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(C(C)=O)c2C)cc1 | CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(C)=O)c(C)c2Cc2ccc(SCC)cc2)[C@H](O)[C@@H](O)[C@@H]1O | null | null | CC1=NC(=CC(=C1)C)C | Acylation | Schotten-Baumann to ester | ab2604cac7a0887c37303ad0fec59fb6a84cf40820c840730a9f7f5636dcc83e | 7ed0ec8c4c25c8af523f531911c9dd0a60119de4cab841f882ce9a65c39be54c | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | null | [] | null | null | 8 | HOUR | To a solution of 1-acetyl-4-[(4-ethylthiophenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methylpyrazole (0.03 g) in 2,4,6-trimethylpyridine (0.5 mL) was added ethyl chloroformate (0.012 mL), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 10% aqueous citric acid solution (5 mL), ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary alcohol | Carbonic Ester | null | null | C1CCOCC1.c1cn[nH]c1.c1ccccc1 | HCl | CC1=NC(=CC(=C1)C)C | null | 8 | CCOC(=O)Cl.CCSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(C(C)=O)c2C)cc1>CC1=NC(=CC(=C1)C)C>CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(C)=O)c(C)c2Cc2ccc(SCC)cc2)[C@H](O)[C@@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4262db90d0af4c18b5a901994af85b83 | CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(=O)OCc3ccccc3)c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O>>CCOC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O | C(C1=CC=CC=C1)OC(=O)N1N=C(C(=C1C)CC1=CC=C(C=C1)OC(C)C)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)COC(=O)OCC>>C(C)OC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC1=NNC(=C1CC1=CC=C(C=C1)OC(C)C)C)O)O)O | O=C(OCc1ccccc1)[n:14]1[n:13][c:12]([O:11][C@@H:10]2[O:9][C@H:8]([CH2:7][O:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[C@@H:33]([OH:34])[C@H:31]([OH:32])[C@H:29]2[OH:30])[c:17]([CH2:18][c:19]2[cH:20][cH:21][c:22]([O:23][CH:24]([CH3:25])[CH3:26])[cH:27][cH:28]2)[c:15]1[CH3:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[O:6][CH2:7][C@H:8]... | CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(=O)OCc3ccccc3)c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O | CCOC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O | null | [C].[Pd] | O1CCCC1 | Reduction | OtherReaction | d587e968ee9de3e2ff573387389369f09c440d928c6e38a3d9128364da37ee2d | 84394d34c591024a84d9393eb3e8adb8ada5a6225c3abafc4dae9aedd4568be4 | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | O=C(-O-C-c1:c:c:c:c:c:1)-[n;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c:5]:1-[C;D1;H3:6]>>[C;D1;H3:6]-[c:5]1:[c:4]:[c:3]:[#7;a:2]:[nH;D2;+0:1]:1 | null | [] | null | null | 3 | HOUR | To a solution of 1-(benzyloxycarbonyl)-3-(6-O-ethoxycarbonyl-β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methylpyrazole (0.17 g) in tetrahydrofuran (4 mL) was added 10% palladium-carbon powder, and the mixture was stirred under hydrogen atmosphere at room temperature for 3 hours. The resulting insoluble mat... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | C1CCOCC1.c1cn[nH]c1.c1ccccc1 | HO- | [C].[Pd].O1CCCC1 | null | 3 | CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(C(=O)OCc3ccccc3)c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O>[C].[Pd].O1CCCC1>CCOC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a5ae2e946a4948aca4eb77ede8b37b41 | Nc1nc(Cl)nc2c1ncn2[C@@H]1O[C@H](CCl)[C@@H](O)[C@H]1O.Nc1nc(I)nc2c1ncn2[C@@H]1O[C@H](CCl)[C@@H](O)[C@H]1O>>Nc1nc(Cl)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O | ClCl.IC=1N=C(C=2N=CN([C@H]3[C@H](O)[C@H](O)[C@@H](CCl)O3)C2N1)N.ClC=1N=C(C=2N=CN([C@H]3[C@H](O)[C@H](O)[C@@H](CCl)O3)C2N1)N>>ClC=1N=C(C=2N=CN([C@H]3[C@H](O)[C@H](O)[C@@H](CO)O3)C2N1)N | Cl[CH2:15][C@H:14]1[O:13][C@@H:12]([n:11]2[c:7]3[n:6][c:4]([Cl:5])[n:3][c:2]([NH2:1])[c:8]3[n:9][cH:10]2)[C@H:19]([OH:20])[C@@H:17]1[OH:18].Nc1nc(I)nc2c1ncn2[C@@H]1O[C@H](CCl)[C@@H]([OH:16])[C@H]1O>>[NH2:1][c:2]1[n:3][c:4]([Cl:5])[n:6][c:7]2[c:8]1[n:9][cH:10][n:11]2[C@@H:12]1[O:13][C@H:14]([CH2:15][OH:16])[C@@H:17]([OH... | Nc1nc(Cl)nc2c1ncn2[C@@H]1O[C@H](CCl)[C@@H](O)[C@H]1O.Nc1nc(I)nc2c1ncn2[C@@H]1O[C@H](CCl)[C@@H](O)[C@H]1O | Nc1nc(Cl)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 194871386fe34c7e62ea477c018dca459772fd4a44ef1daa20875dd076d9b80e | d0329aba55390fb73663ae2fd72c3b277f7b650cbad5bb393037c5158443d08c | c1ncc2ncn([C@H]3CCCO3)c2n1 | Cl-C-[C@H]1-O-[C@H](-n2:c:n:c3:c(-N):n:c(-I):n:c:3:2)-[C@@H](-O)-[C@@H]-1-[OH;D1;+0:1].Cl-[CH2;D2;+0:2]-[C:3](-[C:4])-[#8:5]-[C:6]>>[C:6]-[#8:5]-[C:3](-[CH2;D2;+0:2]-[OH;D1;+0:1])-[C:4] | null | [] | null | null | null | null | In yet another route the 5′-substituent was introduced prior to C2-substitution to circumvent all problems met in the previous routes. The method of Robins20 yielded 5′-deoxy-2-iodo-5′-chloroadenosine from 2-iodoadenosine (1). However, besides the 5′-hydroxyl group, also the 2-iodo group of 1 was replaced by chlorine t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Primary halide.Ether.Secondary alcohol.Secondary alcohol.Primary amine | Primary alcohol | c1ncc2[nH]cnc2n1.C1CCOC1 | null | c1ncc2[nH]cnc2n1.C1CCOC1 | HCl.I- | null | null | null | Nc1nc(Cl)nc2c1ncn2[C@@H]1O[C@H](CCl)[C@@H](O)[C@H]1O.Nc1nc(I)nc2c1ncn2[C@@H]1O[C@H](CCl)[C@@H](O)[C@H]1O>>Nc1nc(Cl)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ecf7348b03414725beb44f80588a50aa | COC[C@H]1O[C@@H](n2cnc3c(Cl)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NC1CCCC1>>COC[C@H]1O[C@@H](n2cnc3c(NC4CCCC4)ncnc32)[C@H](O)[C@@H]1O | ClC1=C2N=CN(C2=NC=N1)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC.C1(CCCC1)N>>C1(CCCC1)NC=1C=2N=CN([C@H]3[C@H](O)[C@H](O)[C@@H](COC)O3)C2N=CN1 | CC(=O)[O:23][C@H:22]1[C@H:6]([n:7]2[cH:8][n:9][c:10]3[c:11](Cl)[n:18][cH:19][n:20][c:21]23)[O:5][C@H:4]([CH2:3][O:2][CH3:1])[C@H:24]1[O:25]C(C)=O.[NH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1>>[CH3:1][O:2][CH2:3][C@H:4]1[O:5][C@@H:6]([n:7]2[cH:8][n:9][c:10]3[c:11]([NH:12][CH:13]4[CH2:14][CH2:15][CH2:16][CH2:17]4)[n... | COC[C@H]1O[C@@H](n2cnc3c(Cl)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NC1CCCC1 | COC[C@H]1O[C@@H](n2cnc3c(NC4CCCC4)ncnc32)[C@H](O)[C@@H]1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 81607f2c1ac92882bcefa60134c8989268991a407436046a8187094e2509bf56 | b0ffde2ea7300acd54f7fec2dbf875bd9e51732578e96c453674091da31aef8e | c1nc(NC2CCCC2)c2ncn([C@H]3CCCO3)c2n1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3](-[O;H0;D2;+0:4]-C(-C)=O)-[C:5]-[#8:6]-[C:7]-1-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]2:[c:12]:1:[#7;a:13]:[c:14]:[#7;a:15]:[c;H0;D3;+0:16]:2-Cl.[C:17]-[C:18](-[NH2;D1;+0:19])-[C:20]>>[C:17]-[C:18](-[NH;D2;+0:19]-[c;H0;D3;+0:16]1:[#7;a:15]:[c:14]:[#7;a:13]:[c:12]2:[#7;a:8](-[C:7]3-[#8:6]-[C:... | null | [] | null | null | null | null | Method B. The reaction was carried out with 6-chloro-9-(2,3-di-O-acetyl-5-O-methyl-β-D-ribofuranosyl)-purine (60, 589 mg, 1.53 mmol) and cyclopentylamine (2.3 mmol, 227 μl). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 476 mg (1.36 mmol, 89%), mp 164–166° C.; Rf 0.51 (eluens 10% M... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester.Primary amine | Secondary alcohol.Secondary alcohol.Secondary amine | c1ncnc2[nH]cnc12 | c1ncnc2[nH]cnc12 | C1CCOC1.C1CCCC1.c1ncnc2[nH]cnc12 | HCl | null | null | null | COC[C@H]1O[C@@H](n2cnc3c(Cl)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NC1CCCC1>>COC[C@H]1O[C@@H](n2cnc3c(NC4CCCC4)ncnc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-29a8a013d9914b9b803ff6aed2e6c1d9 | COC[C@H]1O[C@@H](n2cnc3c(Cl)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NCc1cccc(I)c1>>COC[C@H]1O[C@@H](n2cnc3c(NCc4cccc(I)c4)ncnc32)[C@H](O)[C@@H]1O | ClC1=C2N=CN(C2=NC=N1)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC.IC=1C=C(CN)C=CC1.Cl>>IC=1C=C(CNC=2C=3N=CN([C@H]4[C@H](O)[C@H](O)[C@@H](COC)O4)C3N=CN2)C=CC1 | CC(=O)[O:26][C@H:25]1[C@H:6]([n:7]2[cH:8][n:9][c:10]3[c:11](Cl)[n:21][cH:22][n:23][c:24]23)[O:5][C@H:4]([CH2:3][O:2][CH3:1])[C@H:27]1[O:28]C(C)=O.[NH2:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][c:18]([I:19])[cH:20]1>>[CH3:1][O:2][CH2:3][C@H:4]1[O:5][C@@H:6]([n:7]2[cH:8][n:9][c:10]3[c:11]([NH:12][CH2:13][c:14]4[cH:15][cH:1... | COC[C@H]1O[C@@H](n2cnc3c(Cl)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NCc1cccc(I)c1 | COC[C@H]1O[C@@H](n2cnc3c(NCc4cccc(I)c4)ncnc32)[C@H](O)[C@@H]1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 81607f2c1ac92882bcefa60134c8989268991a407436046a8187094e2509bf56 | b0ffde2ea7300acd54f7fec2dbf875bd9e51732578e96c453674091da31aef8e | c1ccc(CNc2ncnc3c2ncn3[C@H]2CCCO2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3](-[O;H0;D2;+0:4]-C(-C)=O)-[C:5]-[#8:6]-[C:7]-1-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]2:[c:12]:1:[#7;a:13]:[c:14]:[#7;a:15]:[c;H0;D3;+0:16]:2-Cl.[NH2;D1;+0:17]-[C:18]-[c:19]>>[OH;D1;+0:1]-[C:2]1-[C:3](-[OH;D1;+0:4])-[C:5]-[#8:6]-[C:7]-1-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]2:[c:12]:1:[#7;a:13]:[c... | null | [] | null | null | null | null | Method B. The reaction was carried out with 6-chloro-9-(2,3-di-O-acetyl-5-O-methyl-β-D-ribofuranosyl)-purine (60, 363 mg, 0.94 mmol) and 3-iodobenzylamine.HCl (1.41 mmol, 380 mg). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 397 mg (0.80 mmol, 85%), mp 155–157° C.; Rf 0.54 (eluens... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester.Primary amine | Secondary alcohol.Secondary alcohol.Secondary amine | c1ncnc2[nH]cnc12 | c1ncnc2[nH]cnc12 | C1CCOC1.c1ccccc1.c1ncnc2[nH]cnc12 | HCl | null | null | null | COC[C@H]1O[C@@H](n2cnc3c(Cl)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NCc1cccc(I)c1>>COC[C@H]1O[C@@H](n2cnc3c(NCc4cccc(I)c4)ncnc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fc7530688a2b4b59b6358241b17eba03 | COC[C@H]1O[C@@H](n2cnc3c(Cl)nc(Cl)nc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NC1CCCC1>>COC[C@H]1O[C@@H](n2cnc3c(NC4CCCC4)nc(Cl)nc32)[C@H](O)[C@@H]1O | ClC1=NC(=C2N=CN(C2=N1)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC)Cl.C1(CCCC1)N>>C1(CCCC1)NC=1C=2N=CN([C@H]3[C@H](O)[C@H](O)[C@@H](COC)O3)C2N=C(N1)Cl | CC(=O)[O:24][C@H:23]1[C@H:6]([n:7]2[cH:8][n:9][c:10]3[c:11](Cl)[n:18][c:19]([Cl:20])[n:21][c:22]23)[O:5][C@H:4]([CH2:3][O:2][CH3:1])[C@H:25]1[O:26]C(C)=O.[NH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1>>[CH3:1][O:2][CH2:3][C@H:4]1[O:5][C@@H:6]([n:7]2[cH:8][n:9][c:10]3[c:11]([NH:12][CH:13]4[CH2:14][CH2:15][CH2:16][CH2... | COC[C@H]1O[C@@H](n2cnc3c(Cl)nc(Cl)nc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NC1CCCC1 | COC[C@H]1O[C@@H](n2cnc3c(NC4CCCC4)nc(Cl)nc32)[C@H](O)[C@@H]1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b5e5090d9c212d342e73833e2327e4c11ac049b9674b042645347d7b36ec0163 | b0ffde2ea7300acd54f7fec2dbf875bd9e51732578e96c453674091da31aef8e | c1nc(NC2CCCC2)c2ncn([C@H]3CCCO3)c2n1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3](-[O;H0;D2;+0:4]-C(-C)=O)-[C:5]-[#8:6]-[C:7]-1-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]2:[c:12]:1:[#7;a:13]:[c:14]:[#7;a:15]:[c;H0;D3;+0:16]:2-Cl.[C:17]-[C:18](-[NH2;D1;+0:19])-[C:20]>>[C:17]-[C:18](-[NH;D2;+0:19]-[c;H0;D3;+0:16]1:[#7;a:15]:[c:14]:[#7;a:13]:[c:12]2:[#7;a:8](-[C:7]3-[#8:6]-[C:... | null | [] | null | null | null | null | Method B. The reaction was carried out with 2,6-dichloro-9-(2,3-di-O-acetyl-5-O-methyl-β-D-ribofuranosyl)-purine (61, 505 mg, 1.2 mmol) and cyclopentylamine (1.8 mmol, 178 μL). The mixture was purified by column chromatography (eluens 2% MeOH in CH2Cl2). Yield 364 mg (0.95 mmol, 79%), mp 124–126° C.; Rf 0.15 (eluens 2%... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester.Primary amine | Secondary alcohol.Secondary alcohol.Secondary amine | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | C1CCOC1.C1CCCC1.c1ncc2nc[nH]c2n1 | HCl | null | null | null | COC[C@H]1O[C@@H](n2cnc3c(Cl)nc(Cl)nc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NC1CCCC1>>COC[C@H]1O[C@@H](n2cnc3c(NC4CCCC4)nc(Cl)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-26f4648a589c472e97796c0f8fadc0ad | COC[C@H]1O[C@@H](n2cnc3c(Cl)nc(Cl)nc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NCc1cccc(I)c1>>COC[C@H]1O[C@@H](n2cnc3c(NCc4cccc(I)c4)nc(Cl)nc32)[C@H](O)[C@@H]1O | ClC1=NC(=C2N=CN(C2=N1)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC)Cl.IC=1C=C(CN)C=CC1.Cl>>IC=1C=C(CNC=2C=3N=CN([C@H]4[C@H](O)[C@H](O)[C@@H](COC)O4)C3N=C(N2)Cl)C=CC1 | CC(=O)[O:27][C@H:26]1[C@H:6]([n:7]2[cH:8][n:9][c:10]3[c:11](Cl)[n:21][c:22]([Cl:23])[n:24][c:25]23)[O:5][C@H:4]([CH2:3][O:2][CH3:1])[C@H:28]1[O:29]C(C)=O.[NH2:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][c:18]([I:19])[cH:20]1>>[CH3:1][O:2][CH2:3][C@H:4]1[O:5][C@@H:6]([n:7]2[cH:8][n:9][c:10]3[c:11]([NH:12][CH2:13][c:14]4[cH:... | COC[C@H]1O[C@@H](n2cnc3c(Cl)nc(Cl)nc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NCc1cccc(I)c1 | COC[C@H]1O[C@@H](n2cnc3c(NCc4cccc(I)c4)nc(Cl)nc32)[C@H](O)[C@@H]1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b5e5090d9c212d342e73833e2327e4c11ac049b9674b042645347d7b36ec0163 | b0ffde2ea7300acd54f7fec2dbf875bd9e51732578e96c453674091da31aef8e | c1ccc(CNc2ncnc3c2ncn3[C@H]2CCCO2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3](-[O;H0;D2;+0:4]-C(-C)=O)-[C:5]-[#8:6]-[C:7]-1-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]2:[c:12]:1:[#7;a:13]:[c:14]:[#7;a:15]:[c;H0;D3;+0:16]:2-Cl.[NH2;D1;+0:17]-[C:18]-[c:19]>>[OH;D1;+0:1]-[C:2]1-[C:3](-[OH;D1;+0:4])-[C:5]-[#8:6]-[C:7]-1-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]2:[c:12]:1:[#7;a:13]:[c... | null | [] | null | null | null | null | Method B. The reaction was carried out with 2,6-dichloro-9-(2,3-di-O-acetyl-5-O-methyl-β-D-ribofuranosyl)-purine (61, 372 mg, 0.89 mmol) and 3-iodobenzylamine.HCl (1.34 mmol, 360 mg). The mixture was purified by column chromatography (eluens 2% MeOH in CH2Cl2). Yield 383 mg (0.72 mmol, 81%), mp 84–86° C.; Rf 0.59 (10% ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester.Primary amine | Secondary alcohol.Secondary alcohol.Secondary amine | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | C1CCOC1.c1ccccc1.c1ncc2nc[nH]c2n1 | HCl | null | null | null | COC[C@H]1O[C@@H](n2cnc3c(Cl)nc(Cl)nc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NCc1cccc(I)c1>>COC[C@H]1O[C@@H](n2cnc3c(NCc4cccc(I)c4)nc(Cl)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-67dd4af9dd1347f5969c02662dbd86bf | CCOC[C@H]1O[C@@H](n2cnc3c(Cl)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NC1CCCC1>>CCOC[C@H]1O[C@@H](n2cnc3c(NC4CCCC4)ncnc32)[C@H](O)[C@@H]1O | ClC1=C2N=CN(C2=NC=N1)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COCC.C1(CCCC1)N>>C1(CCCC1)NC=1C=2N=CN([C@H]3[C@H](O)[C@H](O)[C@@H](COCC)O3)C2N=CN1 | CC(=O)[O:24][C@H:23]1[C@H:7]([n:8]2[cH:9][n:10][c:11]3[c:12](Cl)[n:19][cH:20][n:21][c:22]23)[O:6][C@H:5]([CH2:4][O:3][CH2:2][CH3:1])[C@H:25]1[O:26]C(C)=O.[NH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1>>[CH3:1][CH2:2][O:3][CH2:4][C@H:5]1[O:6][C@@H:7]([n:8]2[cH:9][n:10][c:11]3[c:12]([NH:13][CH:14]4[CH2:15][CH2:16][CH2... | CCOC[C@H]1O[C@@H](n2cnc3c(Cl)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NC1CCCC1 | CCOC[C@H]1O[C@@H](n2cnc3c(NC4CCCC4)ncnc32)[C@H](O)[C@@H]1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 81607f2c1ac92882bcefa60134c8989268991a407436046a8187094e2509bf56 | b0ffde2ea7300acd54f7fec2dbf875bd9e51732578e96c453674091da31aef8e | c1nc(NC2CCCC2)c2ncn([C@H]3CCCO3)c2n1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3](-[O;H0;D2;+0:4]-C(-C)=O)-[C:5]-[#8:6]-[C:7]-1-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]2:[c:12]:1:[#7;a:13]:[c:14]:[#7;a:15]:[c;H0;D3;+0:16]:2-Cl.[C:17]-[C:18](-[NH2;D1;+0:19])-[C:20]>>[C:17]-[C:18](-[NH;D2;+0:19]-[c;H0;D3;+0:16]1:[#7;a:15]:[c:14]:[#7;a:13]:[c:12]2:[#7;a:8](-[C:7]3-[#8:6]-[C:... | null | [] | null | null | null | null | Method B. The reaction was carried out with 6-chloro-9-(2,3-di-O-acetyl-5-O-ethyl-β-D-ribofuranosyl)-purine (62, 502 mg, 1.26 mmol) and cyclopentylamine (1.89 mmol, 187 μL). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 316 mg (0.87 mmol, 69%), mp 134–136° C.; Rf 0.49 (eluens 10% M... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester.Primary amine | Secondary alcohol.Secondary alcohol.Secondary amine | c1ncnc2[nH]cnc12 | c1ncnc2[nH]cnc12 | C1CCOC1.C1CCCC1.c1ncnc2[nH]cnc12 | HCl | null | null | null | CCOC[C@H]1O[C@@H](n2cnc3c(Cl)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NC1CCCC1>>CCOC[C@H]1O[C@@H](n2cnc3c(NC4CCCC4)ncnc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f987bac8e4204a08947a7a5ff7139be3 | CCOC[C@H]1O[C@@H](n2cnc3c(Cl)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NCc1cccc(I)c1>>CCOC[C@H]1O[C@@H](n2cnc3c(NCc4cccc(I)c4)ncnc32)[C@H](O)[C@@H]1O | ClC1=C2N=CN(C2=NC=N1)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COCC.IC=1C=C(CN)C=CC1.Cl>>IC=1C=C(CNC=2C=3N=CN([C@H]4[C@H](O)[C@H](O)[C@@H](COCC)O4)C3N=CN2)C=CC1 | CC(=O)[O:27][C@H:26]1[C@H:7]([n:8]2[cH:9][n:10][c:11]3[c:12](Cl)[n:22][cH:23][n:24][c:25]23)[O:6][C@H:5]([CH2:4][O:3][CH2:2][CH3:1])[C@H:28]1[O:29]C(C)=O.[NH2:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][c:19]([I:20])[cH:21]1>>[CH3:1][CH2:2][O:3][CH2:4][C@H:5]1[O:6][C@@H:7]([n:8]2[cH:9][n:10][c:11]3[c:12]([NH:13][CH2:14][c:... | CCOC[C@H]1O[C@@H](n2cnc3c(Cl)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NCc1cccc(I)c1 | CCOC[C@H]1O[C@@H](n2cnc3c(NCc4cccc(I)c4)ncnc32)[C@H](O)[C@@H]1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 81607f2c1ac92882bcefa60134c8989268991a407436046a8187094e2509bf56 | b0ffde2ea7300acd54f7fec2dbf875bd9e51732578e96c453674091da31aef8e | c1ccc(CNc2ncnc3c2ncn3[C@H]2CCCO2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3](-[O;H0;D2;+0:4]-C(-C)=O)-[C:5]-[#8:6]-[C:7]-1-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]2:[c:12]:1:[#7;a:13]:[c:14]:[#7;a:15]:[c;H0;D3;+0:16]:2-Cl.[NH2;D1;+0:17]-[C:18]-[c:19]>>[OH;D1;+0:1]-[C:2]1-[C:3](-[OH;D1;+0:4])-[C:5]-[#8:6]-[C:7]-1-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]2:[c:12]:1:[#7;a:13]:[c... | null | [] | null | null | null | null | Method B. The reaction was carried out with 6-chloro-9-(2,3-di-O-acetyl-5-O-ethyl-β-D-ribofuranosyl)-purine (62, 367 mg, 0.92 mmol) and 3-iodobenzylamine.HCl (1.38 mmol, 372 mg). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 339 mg (0.66 mmol, 72%), mp 164–166° C.; Rf 0.40 (10% MeO... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester.Primary amine | Secondary alcohol.Secondary alcohol.Secondary amine | c1ncnc2[nH]cnc12 | c1ncnc2[nH]cnc12 | C1CCOC1.c1ccccc1.c1ncnc2[nH]cnc12 | HCl | null | null | null | CCOC[C@H]1O[C@@H](n2cnc3c(Cl)ncnc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NCc1cccc(I)c1>>CCOC[C@H]1O[C@@H](n2cnc3c(NCc4cccc(I)c4)ncnc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-227c8853310445f6bfa8c4ba4f49e960 | CCOC[C@H]1O[C@@H](n2cnc3c(Cl)nc(Cl)nc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NC1CCCC1>>CCOC[C@H]1O[C@@H](n2cnc3c(NC4CCCC4)nc(Cl)nc32)[C@H](O)[C@@H]1O | ClC1=NC(=C2N=CN(C2=N1)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COCC)Cl.C1(CCCC1)N>>C1(CCCC1)NC=1C=2N=CN([C@H]3[C@H](O)[C@H](O)[C@@H](COCC)O3)C2N=C(N1)Cl | CC(=O)[O:25][C@H:24]1[C@H:7]([n:8]2[cH:9][n:10][c:11]3[c:12](Cl)[n:19][c:20]([Cl:21])[n:22][c:23]23)[O:6][C@H:5]([CH2:4][O:3][CH2:2][CH3:1])[C@H:26]1[O:27]C(C)=O.[NH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1>>[CH3:1][CH2:2][O:3][CH2:4][C@H:5]1[O:6][C@@H:7]([n:8]2[cH:9][n:10][c:11]3[c:12]([NH:13][CH:14]4[CH2:15][CH2... | CCOC[C@H]1O[C@@H](n2cnc3c(Cl)nc(Cl)nc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NC1CCCC1 | CCOC[C@H]1O[C@@H](n2cnc3c(NC4CCCC4)nc(Cl)nc32)[C@H](O)[C@@H]1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b5e5090d9c212d342e73833e2327e4c11ac049b9674b042645347d7b36ec0163 | b0ffde2ea7300acd54f7fec2dbf875bd9e51732578e96c453674091da31aef8e | c1nc(NC2CCCC2)c2ncn([C@H]3CCCO3)c2n1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3](-[O;H0;D2;+0:4]-C(-C)=O)-[C:5]-[#8:6]-[C:7]-1-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]2:[c:12]:1:[#7;a:13]:[c:14]:[#7;a:15]:[c;H0;D3;+0:16]:2-Cl.[C:17]-[C:18](-[NH2;D1;+0:19])-[C:20]>>[C:17]-[C:18](-[NH;D2;+0:19]-[c;H0;D3;+0:16]1:[#7;a:15]:[c:14]:[#7;a:13]:[c:12]2:[#7;a:8](-[C:7]3-[#8:6]-[C:... | null | [] | null | null | null | null | Method B. The reaction was carried out with 2,6-dichloro-9-(2,3-di-O-acetyl-5-O-ethyl-β-D-ribofuranosyl)-purine (63, 505 mg, 1.16 mmol) and cyclopentylamine (1.74 mmol, 172 μL). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 323 mg (0.81 mmol, 70%), mp 114–116° C.; Rf 0.55 (10% MeOH... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester.Primary amine | Secondary alcohol.Secondary alcohol.Secondary amine | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | C1CCOC1.C1CCCC1.c1ncc2nc[nH]c2n1 | HCl | null | null | null | CCOC[C@H]1O[C@@H](n2cnc3c(Cl)nc(Cl)nc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NC1CCCC1>>CCOC[C@H]1O[C@@H](n2cnc3c(NC4CCCC4)nc(Cl)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e0bdacdc5f54682a3efd2afc10f8706 | CCOC[C@H]1O[C@@H](n2cnc3c(Cl)nc(Cl)nc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NCc1cccc(I)c1>>CCOC[C@H]1O[C@@H](n2cnc3c(NCc4cccc(I)c4)nc(Cl)nc32)[C@H](O)[C@@H]1O | ClC1=NC(=C2N=CN(C2=N1)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COCC)Cl.IC=1C=C(CN)C=CC1.Cl>>IC=1C=C(CNC=2C=3N=CN([C@H]4[C@H](O)[C@H](O)[C@@H](COCC)O4)C3N=C(N2)Cl)C=CC1 | CC(=O)[O:28][C@H:27]1[C@H:7]([n:8]2[cH:9][n:10][c:11]3[c:12](Cl)[n:22][c:23]([Cl:24])[n:25][c:26]23)[O:6][C@H:5]([CH2:4][O:3][CH2:2][CH3:1])[C@H:29]1[O:30]C(C)=O.[NH2:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][c:19]([I:20])[cH:21]1>>[CH3:1][CH2:2][O:3][CH2:4][C@H:5]1[O:6][C@@H:7]([n:8]2[cH:9][n:10][c:11]3[c:12]([NH:13][CH... | CCOC[C@H]1O[C@@H](n2cnc3c(Cl)nc(Cl)nc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NCc1cccc(I)c1 | CCOC[C@H]1O[C@@H](n2cnc3c(NCc4cccc(I)c4)nc(Cl)nc32)[C@H](O)[C@@H]1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b5e5090d9c212d342e73833e2327e4c11ac049b9674b042645347d7b36ec0163 | b0ffde2ea7300acd54f7fec2dbf875bd9e51732578e96c453674091da31aef8e | c1ccc(CNc2ncnc3c2ncn3[C@H]2CCCO2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3](-[O;H0;D2;+0:4]-C(-C)=O)-[C:5]-[#8:6]-[C:7]-1-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]2:[c:12]:1:[#7;a:13]:[c:14]:[#7;a:15]:[c;H0;D3;+0:16]:2-Cl.[NH2;D1;+0:17]-[C:18]-[c:19]>>[OH;D1;+0:1]-[C:2]1-[C:3](-[OH;D1;+0:4])-[C:5]-[#8:6]-[C:7]-1-[#7;a:8]1:[c:9]:[#7;a:10]:[c:11]2:[c:12]:1:[#7;a:13]:[c... | null | [] | null | null | null | null | Method B. The reaction was carried out with 2,6-dichloro-9-(2,3-di-O-acetyl-5-O-ethyl-β-D-ribofuranosyl)-purine (63, 375 mg, 0.87 mmol) and 3-iodobenzylamine.HCl (1.31 mmol, 352 mg). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 366 mg (0.67 mmol, 77%), mp 80–82° C.; Rf 0.53 (10% M... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester.Primary amine | Secondary alcohol.Secondary alcohol.Secondary amine | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | C1CCOC1.c1ccccc1.c1ncc2nc[nH]c2n1 | HCl | null | null | null | CCOC[C@H]1O[C@@H](n2cnc3c(Cl)nc(Cl)nc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O.NCc1cccc(I)c1>>CCOC[C@H]1O[C@@H](n2cnc3c(NCc4cccc(I)c4)nc(Cl)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-33f7d48ca5fb4896af7983cbb4253f72 | CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](COC2CC2)O[C@H]1n1cnc2c(Cl)nc(Cl)nc21.NC1CCCC1>>O[C@@H]1[C@H](O)[C@@H](COC2CC2)O[C@H]1n1cnc2c(NC3CCCC3)nc(Cl)nc21 | ClC1=NC(=C2N=CN(C2=N1)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC1CC1)Cl.C1(CCCC1)N>>C1(CCCC1)NC=1C=2N=CN([C@H]3[C@H](O)[C@H](O)[C@@H](COC4CC4)O3)C2N=C(N1)Cl | CC(=O)[O:1][C@@H:2]1[C@H:3]([O:4]C(C)=O)[C@@H:5]([CH2:6][O:7][CH:8]2[CH2:9][CH2:10]2)[O:11][C@H:12]1[n:13]1[cH:14][n:15][c:16]2[c:17](Cl)[n:24][c:25]([Cl:26])[n:27][c:28]12.[NH2:18][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1>>[OH:1][C@@H:2]1[C@H:3]([OH:4])[C@@H:5]([CH2:6][O:7][CH:8]2[CH2:9][CH2:10]2)[O:11][C@H:12]1[n:13]... | CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](COC2CC2)O[C@H]1n1cnc2c(Cl)nc(Cl)nc21.NC1CCCC1 | O[C@@H]1[C@H](O)[C@@H](COC2CC2)O[C@H]1n1cnc2c(NC3CCCC3)nc(Cl)nc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b5e5090d9c212d342e73833e2327e4c11ac049b9674b042645347d7b36ec0163 | b0ffde2ea7300acd54f7fec2dbf875bd9e51732578e96c453674091da31aef8e | c1nc(NC2CCCC2)c2ncn([C@H]3CC[C@@H](COC4CC4)O3)c2n1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3](-[#7;a:4]2:[c:5]:[#7;a:6]:[c:7]3:[c:8]:2:[#7;a:9]:[c:10]:[#7;a:11]:[c;H0;D3;+0:12]:3-Cl)-[#8:13]-[C:14]-[C:15]-1-[O;H0;D2;+0:16]-C(-C)=O.[C:17]-[C:18](-[NH2;D1;+0:19])-[C:20]>>[C:17]-[C:18](-[NH;D2;+0:19]-[c;H0;D3;+0:12]1:[#7;a:11]:[c:10]:[#7;a:9]:[c:8]2:[#7;a:4](-[C:3]3-[#8:13]-[C:1... | null | [] | null | null | null | null | Method B. The reaction was carried out with 2,6-dichloro-9-(2,3-di-O-acetyl-5-O-cyclopropyl-β-D-ribofuranosyl)-purine (65, 543 mg, 1.22 mmol) and cyclopentylamine (1.83 mmol, 180 μL). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 400 mg (0.98 mmol, 80%), mp 104–106° C.; Rf 0.51 (10... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester.Primary amine | Secondary alcohol.Secondary alcohol.Secondary amine | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | C1CCOC1.C1CC1.C1CCCC1.c1ncc2nc[nH]c2n1 | HCl | null | null | null | CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](COC2CC2)O[C@H]1n1cnc2c(Cl)nc(Cl)nc21.NC1CCCC1>>O[C@@H]1[C@H](O)[C@@H](COC2CC2)O[C@H]1n1cnc2c(NC3CCCC3)nc(Cl)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6fb65ac27b4e4300a6d9d193585491c1 | CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](COC2CC2)O[C@H]1n1cnc2c(Cl)nc(Cl)nc21.NCc1cccc(I)c1>>O[C@@H]1[C@H](O)[C@@H](COC2CC2)O[C@H]1n1cnc2c(NCc3cccc(I)c3)nc(Cl)nc21 | ClC1=NC(=C2N=CN(C2=N1)[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC1CC1)Cl.IC=1C=C(CN)C=CC1.Cl>>IC=1C=C(CNC=2C=3N=CN([C@H]4[C@H](O)[C@H](O)[C@@H](COC5CC5)O4)C3N=C(N2)Cl)C=CC1 | CC(=O)[O:1][C@@H:2]1[C@H:3]([O:4]C(C)=O)[C@@H:5]([CH2:6][O:7][CH:8]2[CH2:9][CH2:10]2)[O:11][C@H:12]1[n:13]1[cH:14][n:15][c:16]2[c:17](Cl)[n:27][c:28]([Cl:29])[n:30][c:31]12.[NH2:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][c:24]([I:25])[cH:26]1>>[OH:1][C@@H:2]1[C@H:3]([OH:4])[C@@H:5]([CH2:6][O:7][CH:8]2[CH2:9][CH2:10]2)[O:1... | CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](COC2CC2)O[C@H]1n1cnc2c(Cl)nc(Cl)nc21.NCc1cccc(I)c1 | O[C@@H]1[C@H](O)[C@@H](COC2CC2)O[C@H]1n1cnc2c(NCc3cccc(I)c3)nc(Cl)nc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b5e5090d9c212d342e73833e2327e4c11ac049b9674b042645347d7b36ec0163 | b0ffde2ea7300acd54f7fec2dbf875bd9e51732578e96c453674091da31aef8e | c1ccc(CNc2ncnc3c2ncn3[C@H]2CC[C@@H](COC3CC3)O2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3](-[#7;a:4]2:[c:5]:[#7;a:6]:[c:7]3:[c:8]:2:[#7;a:9]:[c:10]:[#7;a:11]:[c;H0;D3;+0:12]:3-Cl)-[#8:13]-[C:14]-[C:15]-1-[O;H0;D2;+0:16]-C(-C)=O.[NH2;D1;+0:17]-[C:18]-[c:19]>>[OH;D1;+0:1]-[C:2]1-[C:3](-[#7;a:4]2:[c:5]:[#7;a:6]:[c:7]3:[c:8]:2:[#7;a:9]:[c:10]:[#7;a:11]:[c;H0;D3;+0:12]:3-[NH;D2... | null | [] | null | null | null | null | Method B. The reaction was carried out with 2,6-dichloro-9-(2,3-di-O-acetyl-5-O-cyclopropyl-β-D-ribofuranosyl)-purine (65, 483 mg, 1.08 mmol) and 3-iodobenzylamine.HCl (1.63 mmol, 439 mg). The mixture was purified by column chromatography (eluens 5% MeOH in CH2Cl2). Yield 435 mg (0.78 mmol, 72%), mp 94–96° C.; Rf 0.49 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester.Primary amine | Secondary alcohol.Secondary alcohol.Secondary amine | c1ncc2nc[nH]c2n1 | c1ncc2nc[nH]c2n1 | C1CCOC1.C1CC1.c1ccccc1.c1ncc2nc[nH]c2n1 | HCl | null | null | null | CC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](COC2CC2)O[C@H]1n1cnc2c(Cl)nc(Cl)nc21.NCc1cccc(I)c1>>O[C@@H]1[C@H](O)[C@@H](COC2CC2)O[C@H]1n1cnc2c(NCc3cccc(I)c3)nc(Cl)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4e344923b8de4e4cb0fa455e94767689 | CCOC(=O)N1CCN(C(=O)C(CCC(=O)OC(C)(C)C)NC(=O)OCc2ccccc2)CC1>>CCOC(=O)N1CCN(C(=O)C(N)CCC(=O)OC(C)(C)C)CC1 | C(C)OC(=O)N1CCN(CC1)C(=O)C(CCC(=O)OC(C)(C)C)NC(=O)OCC1=CC=CC=C1>>C(C)OC(=O)N1CCN(CC1)C(=O)C(CCC(=O)OC(C)(C)C)N | O=C(OCc1ccccc1)[NH:13][CH:12]([C:10]([N:9]1[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:24][CH2:23]1)=[O:11])[CH2:14][CH2:15][C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[CH:12]([NH2:13])[CH2:14][CH2:15][C:16](=[O:17])[O:1... | CCOC(=O)N1CCN(C(=O)C(CCC(=O)OC(C)(C)C)NC(=O)OCc2ccccc2)CC1 | CCOC(=O)N1CCN(C(=O)C(N)CCC(=O)OC(C)(C)C)CC1 | null | [Pd] | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | C1CNCCN1 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7])-[C:8]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#7:6](-[C:7])-[C:8] | 86.9 | [{"value": 86.9, "product": "C(C)OC(=O)N1CCN(CC1)C(=O)C(CCC(=O)OC(C)(C)C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Alternatively, N-benzyloxycarbonyl-L-glutamic acid y-t-butyl ester (34 g, 100 mmol) and EDCI (22 g, 110 mmol), HOBT (15 g, 110 mmol) were combined in 800 mL CH2Cl2 with triethylamine (24 mL, 172 mmol). The resulting reaction mixture was stirred at ambient temperature for 20 minutes, then 1-ethoxycarbonylpiperazine (18 ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | C1C[NH]CC[NH]1 | HO- | [Pd].CO | null | 1 | CCOC(=O)N1CCN(C(=O)C(CCC(=O)OC(C)(C)C)NC(=O)OCc2ccccc2)CC1>[Pd].CO>CCOC(=O)N1CCN(C(=O)C(N)CCC(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c21a7c9012845b8aa65e0a62e4a565a | COC(=O)c1cc(O)c2ccc(C)cc2n1>>Cc1ccc2c(O)cc(C(=O)O)nc2c1 | [Li+].[OH-].CC1=CC=C2C(=CC(=NC2=C1)C(=O)OC)O>>CC1=CC=C2C(=CC(=NC2=C1)C(=O)O)O | C[O:12][C:10]([c:9]1[cH:8][c:6]([OH:7])[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:15][c:14]2[n:13]1)=[O:11]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([OH:7])[cH:8][c:9]([C:10](=[O:11])[OH:12])[n:13][c:14]2[cH:15]1 | COC(=O)c1cc(O)c2ccc(C)cc2n1 | Cc1ccc2c(O)cc(C(=O)O)nc2c1 | null | null | CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2ncccc2c1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 98 | [{"value": 98.0, "product": "CC1=CC=C2C(=CC(=NC2=C1)C(=O)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.0, "product": "CC1=CC=C2C(=CC(=NC2=C1)C(=O)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 7-methyl-4-hydroxy-2-methoxycarbonylquinoline (6.45 g, 30.14 mmol) was suspended in MeOH (150 mL) and water (100 mL), and LiOH (3.08 g, 75.5 mmol) was added and stirred at ambient temperature for 2 hours. The methanol was evaporated in vacuo and residue was crystallized by addition of 2N hydrochloric acid. The resultin... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccc2ncccc2c1 | Other | CO.O | null | 2 | COC(=O)c1cc(O)c2ccc(C)cc2n1>CO.O>Cc1ccc2c(O)cc(C(=O)O)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c78937719c06435bb816f877129f639e | Cc1c(Cl)ccc([N+](=O)[O-])c1Cl>>Cc1c(Cl)ccc(N)c1Cl | Cl[Sn]Cl.O.ClC1=C(C(=CC=C1[N+](=O)[O-])Cl)C>>ClC1=C(C(=CC=C1N)Cl)C | O=[N+:8]([O-])[c:7]1[cH:6][cH:5][c:3]([Cl:4])[c:2]([CH3:1])[c:9]1[Cl:10]>>[CH3:1][c:2]1[c:3]([Cl:4])[cH:5][cH:6][c:7]([NH2:8])[c:9]1[Cl:10] | Cc1c(Cl)ccc([N+](=O)[O-])c1Cl | Cc1c(Cl)ccc(N)c1Cl | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99.4 | [{"value": 98.0, "product": "ClC1=C(C(=CC=C1N)Cl)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.4, "product": "ClC1=C(C(=CC=C1N)Cl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of SnCl2.H2O (140 g, 0.62 mol) in ethanol (350 mL) was added a solution of 2,6-dichloro-3-nitrotoluene (25 g, 0.12 mol) in ethanol (50 mL). The reaction mixture was refluxed for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in water (100 mL), pH was adjust... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | C(C)O | null | null | Cc1c(Cl)ccc([N+](=O)[O-])c1Cl>C(C)O>Cc1c(Cl)ccc(N)c1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b5891dc96b04f91a5dc14cb3e9eaccd | COC(=O)C#CC(=O)OC.Cc1c(Cl)ccc(N)c1Cl>>COC(=O)C1=Nc2c(cc(Cl)c(C)c2Cl)C(=O)C1 | ClC1=C(C(=CC=C1N)Cl)C.C(#CC(=O)OC)C(=O)OC>>COC(=O)C1=NC2=C(C(=C(C=C2C(C1)=O)Cl)C)Cl | CO[C:16](=[O:17])[C:18]#[C:5][C:3]([O:2][CH3:1])=[O:4].[NH2:6][c:7]1[cH:8][cH:9][c:10]([Cl:11])[c:12]([CH3:13])[c:14]1[Cl:15]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[N:6][c:7]2[c:8]([cH:9][c:10]([Cl:11])[c:12]([CH3:13])[c:14]2[Cl:15])[C:16](=[O:17])[CH2:18]1 | COC(=O)C#CC(=O)OC.Cc1c(Cl)ccc(N)c1Cl | COC(=O)C1=Nc2c(cc(Cl)c(C)c2Cl)C(=O)C1 | null | null | CO | C-C Coupling | OtherReaction | 61fc804c11347f8c552f8c71d7dc4ce5886428f16d518aef71ee84f77f5a9c95 | 343949bacd0ed413c45dfd95c6860d22174d279443176ded9b99285e6cad8fd2 | O=C1CC=Nc2ccccc21 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]:[c:14]>>[C;D1;H3:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[C;H0;D3;+0:4]1=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](:[c:13]:[c:14])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3... | 90.6 | [{"value": 85.0, "product": "COC(=O)C1=NC2=C(C(=C(C=C2C(C1)=O)Cl)C)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "COC(=O)C1=NC2=C(C(=C(C=C2C(C1)=O)Cl)C)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2,6-dichloro-3-aminotoluene (20.5 g, 0.11 mol) in methanol (300 mL) was added dimethyl acetylenedicarboxylate (15 mL, 0.12 mol) and the reaction mixture was refluxed for 2 hours. The reaction mixture was concentrated under reduced pressure to a yellow solid. Diphenyl ether (350 mL) was heated to 230–24... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Ketone.Ester.Substituted imine | c1ccccc1 | C1=Nc2ccccc2CC1 | C1=Nc2ccccc2CC1 | HO- | CO | null | null | COC(=O)C#CC(=O)OC.Cc1c(Cl)ccc(N)c1Cl>CO>COC(=O)C1=Nc2c(cc(Cl)c(C)c2Cl)C(=O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-05ad1be005714557ad95a163c097a8c8 | COC(=O)C1=Nc2c(cc(Cl)c(C)c2Cl)C(=O)C1>>Cc1ccc2c(c1)N=C(C(=O)O)CC2=O | COC(=O)C1=NC2=C(C(=C(C=C2C(C1)=O)Cl)C)Cl.O[Li].O>>C(=O)(O)C1=NC2=CC(=CC=C2C(C1)=O)C | C[O:12][C:10]([C:9]1=[N:8][c:6]2[c:5]([cH:4][c:3](Cl)[c:2]([CH3:1])[c:7]2Cl)[C:14](=[O:15])[CH2:13]1)=[O:11]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[N:8]=[C:9]([C:10](=[O:11])[OH:12])[CH2:13][C:14]2=[O:15] | COC(=O)C1=Nc2c(cc(Cl)c(C)c2Cl)C(=O)C1 | Cc1ccc2c(c1)N=C(C(=O)O)CC2=O | null | [Pd] | CO.O | Deprotection | OtherReaction | 0d8be8be1736f0cc7a7d011c6080f82485510feb0f29ef387af1701ae98d2bec | e8d4453c71c8f9a5295a75d92f53dd519bc5627be0865bd49270128a86291c44 | O=C1CC=Nc2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]=[#7:5]-[c:6]1:[c:7](:[c:8]:[c;H0;D3;+0:9](-Cl):[c:10](-[C;D1;H3:11]):[c;H0;D3;+0:12]:1-Cl)-[C:13]=[O;D1;H0:14]>>[C;D1;H3:11]-[c:10]1:[cH;D2;+0:9]:[c:8]:[c:7](:[c:6](:[cH;D2;+0:12]:1)-[#7:5]=[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])-[C:13]=[O;D1;H0:14] | 98.8 | [{"value": 90.0, "product": "C(=O)(O)C1=NC2=CC(=CC=C2C(C1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.8, "product": "C(=O)(O)C1=NC2=CC(=CC=C2C(C1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | 2-(Methoxycarbonyl)-4-oxo-6,8-dichloro-7-methylquinoline (28.5 g, 99.6 mmol) was suspended in methanol (1 L) and a solution of LiOH.H2O (20.5 g, 0.5 mol) in water (200 mL) was added to the solution. The resulting reaction mixture was stirred at ambient temperature for 0.5 hours. Pd/C (5.8 g) was added to the reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ester | Carboxylic acid | C1=Nc2ccccc2CC1 | C1=Nc2ccccc2CC1 | C1=Nc2ccccc2CC1 | Other | [Pd].CO.O | null | 0.5 | COC(=O)C1=Nc2c(cc(Cl)c(C)c2Cl)C(=O)C1>[Pd].CO.O>Cc1ccc2c(c1)N=C(C(=O)O)CC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b1946fdbc0c24122be9c85cffe1099fa | COC(=O)C#CC(=O)OC.Cc1cc(N)ccc1Cl>>COC(=O)C1=Nc2cc(C)c(Cl)cc2C(=O)C1 | ClC1=C(C=C(N)C=C1)C.C(#CC(=O)OC)C(=O)OC>>COC(=O)C1=NC2=CC(=C(C=C2C(C1)=O)Cl)C | CO[C:15](=[O:16])[C:17]#[C:5][C:3]([O:2][CH3:1])=[O:4].[NH2:6][c:7]1[cH:8][c:9]([CH3:10])[c:11]([Cl:12])[cH:13][cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[N:6][c:7]2[cH:8][c:9]([CH3:10])[c:11]([Cl:12])[cH:13][c:14]2[C:15](=[O:16])[CH2:17]1 | COC(=O)C#CC(=O)OC.Cc1cc(N)ccc1Cl | COC(=O)C1=Nc2cc(C)c(Cl)cc2C(=O)C1 | null | null | CO | C-C Coupling | OtherReaction | 61fc804c11347f8c552f8c71d7dc4ce5886428f16d518aef71ee84f77f5a9c95 | 343949bacd0ed413c45dfd95c6860d22174d279443176ded9b99285e6cad8fd2 | O=C1CC=Nc2ccccc21 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D2;+0:3]#[C;H0;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]:[c:14]>>[C;D1;H3:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[C;H0;D3;+0:4]1=[N;H0;D2;+0:9]-[c:10](:[c:11]):[c;H0;D3;+0:12](:[c:13]:[c:14])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3... | 81.7 | [{"value": 81.7, "product": "COC(=O)C1=NC2=CC(=C(C=C2C(C1)=O)Cl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Alternatively, to a solution of 4-chloro-3-methyl aniline (20.0 g, 0.141 mol) in MeOH (400 mL) was added drop-wise dimethyl acetylenedicarboxylate (21.07 g, 0.148 mol). The reaction mixture was stirred at ambient temperature for 30 minutes. The solvent was removed by evaporation and the residue was added to stirred dip... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Ketone.Ester.Substituted imine | c1ccccc1 | C1=Nc2ccccc2CC1 | C1=Nc2ccccc2CC1 | HO- | CO | null | 0.5 | COC(=O)C#CC(=O)OC.Cc1cc(N)ccc1Cl>CO>COC(=O)C1=Nc2cc(C)c(Cl)cc2C(=O)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-11b76eafc4824bf4a143a7e2a8c5476d | COC(=O)C1=Nc2cc(C)c(Cl)cc2C(=O)C1>>Cc1cc2c(cc1Cl)C(=O)CC(C(=O)O)=N2 | COC(=O)C1=NC2=CC(=C(C=C2C(C1)=O)Cl)C.[OH-].[Li+]>>C(=O)(O)C1=NC2=CC(=C(C=C2C(C1)=O)Cl)C | C[O:15][C:13]([C:12]1=[N:16][c:4]2[cH:3][c:2]([CH3:1])[c:7]([Cl:8])[cH:6][c:5]2[C:9](=[O:10])[CH2:11]1)=[O:14]>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[Cl:8])[C:9](=[O:10])[CH2:11][C:12]([C:13](=[O:14])[OH:15])=[N:16]2 | COC(=O)C1=Nc2cc(C)c(Cl)cc2C(=O)C1 | Cc1cc2c(cc1Cl)C(=O)CC(C(=O)O)=N2 | null | null | CO.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C1CC=Nc2ccccc21 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]=[#7:5]>>[#7:5]=[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 88.7 | [{"value": 88.0, "product": "C(=O)(O)C1=NC2=CC(=C(C=C2C(C1)=O)Cl)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.7, "product": "C(=O)(O)C1=NC2=CC(=C(C=C2C(C1)=O)Cl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 2-Methoxycarbonyl-6-chloro-7-methyl-4-oxoquinoline (7.00 g, 28.00 mmol) was suspended in 300 mL of MeOH and 100 mL of water. Lithium hydroxide (3.40 g, 90 mmol) was added and the reaction was stirred at room temp for 2 hours. The methanol was evaporated in vacuo and the product was crystallized by addition of 2N hydroc... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1=Nc2ccccc2CC1 | Other | CO.O | null | 2 | COC(=O)C1=Nc2cc(C)c(Cl)cc2C(=O)C1>CO.O>Cc1cc2c(cc1Cl)C(=O)CC(C(=O)O)=N2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3e19d64402b74de0a36f2cd83f967d78 | BrCc1ccccc1.O=C(O)c1cc(O)c2ccccc2n1>>O=C(OCc1ccccc1)c1cc(OCc2ccccc2)c2ccccc2n1 | C([O-])([O-])=O.[Cs+].[Cs+].C(=O)(O)C1=NC2=CC=CC=C2C(=C1)O.C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)OC(=O)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=CC=C1 | Br[CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[O:1]=[C:2]([OH:3])[c:11]1[cH:12][c:13]([OH:14])[c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]2[n:28]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:22]2[cH:23][cH:24][cH:... | BrCc1ccccc1.O=C(O)c1cc(O)c2ccccc2n1 | O=C(OCc1ccccc1)c1cc(OCc2ccccc2)c2ccccc2n1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 72d1c2b090053a23ad738a37a3cb5892dd40a7a11cc0ee31c0e0604d86872f07 | 6c958dcb3e552492aca64534cb11a4afa104129654bdbddfbe6a577b0564c983 | O=C(OCc1ccccc1)c1cc(OCc2ccccc2)c2ccccc2n1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C:6](-[OH;D1;+0:7])-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[c:12](-[OH;D1;+0:13]):[c:14]:1>>[O;D1;H0:5]=[C:6](-[O;H0;D2;+0:7]-[C:15]-[c:16])-[c:8]1:[#7;a:9]:[c:10]:[c:11]:[c:12](-[O;H0;D2;+0:13]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:14]:1 | 186.4 | [{"value": 186.4, "product": "C(C1=CC=CC=C1)OC(=O)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 1 | HOUR | 2-carboxy-4-hydroxyquinoline (5 g, 1.0 eq) was dissolved in 50 mL DMF. Cesium carbonate (20 g, 2.3 eq) was added to the solution and the resulting reaction mixture was heated at 50° C. for 20 minutes. Benzyl bromide (10 g, 2.1 eq) was added. The resulting reaction mixture was stirred at 50° C. for 1 hour. Then the reac... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid.Aromatic alcohol | Ester.Ether | null | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2ncccc2c1 | Br- | CN(C)C=O | 50 | 1 | BrCc1ccccc1.O=C(O)c1cc(O)c2ccccc2n1>CN(C)C=O>O=C(OCc1ccccc1)c1cc(OCc2ccccc2)c2ccccc2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ef9c288f8f7f4b24b03af86766954c93 | O=C(OCc1ccccc1)c1cc(OCc2ccccc2)c2ccccc2n1>>O=C(O)c1cc(OCc2ccccc2)c2ccccc2n1 | C(C1=CC=CC=C1)OC(=O)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=CC=C1.[Li+].[OH-]>>C(=O)(O)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=CC=C1 | c1ccc(C[O:3][C:2](=[O:1])[c:4]2[cH:5][c:6]([O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]3[n:21]2)cc1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[n:21]1 | O=C(OCc1ccccc1)c1cc(OCc2ccccc2)c2ccccc2n1 | O=C(O)c1cc(OCc2ccccc2)c2ccccc2n1 | null | null | C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(COc2ccnc3ccccc23)cc1 | [#7;a:1]:[c:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-C-c1:c:c:c:c:c:1>>[#7;a:1]:[c:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5] | 105.8 | [{"value": 105.8, "product": "C(=O)(O)C1=NC2=CC=CC=C2C(=C1)OCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 2-carboxy-4-hydroxyquinoline (5 g, 1.0 eq) was dissolved in 50 mL DMF. Cesium carbonate (20 g, 2.3 eq) was added to the solution and the resulting reaction mixture was heated at 50° C. for 20 minutes. Benzyl bromide (10 g, 2.1 eq) was added. The resulting reaction mixture was stirred at 50° C. for 1 hour. Then the reac... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccccc1.c1ccc2ncccc2c1 | Other | C1CCOC1 | null | 2 | O=C(OCc1ccccc1)c1cc(OCc2ccccc2)c2ccccc2n1>C1CCOC1>O=C(O)c1cc(OCc2ccccc2)c2ccccc2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bcd19a03fab24805954e9d09cca356c1 | Cc1ccc2c(O)cc(C(=O)O)nc2c1.ClP(Cl)(Cl)(Cl)Cl>>Cc1ccc2c(Cl)cc(C(=O)O)nc2c1 | [OH-].[K+].C(=O)(O)C1=NC2=CC(=CC=C2C(=C1)O)C.P(Cl)(Cl)(Cl)(Cl)Cl.[OH-].[Na+]>>C(=O)(O)C1=NC2=CC(=CC=C2C(=C1)Cl)C | O[c:6]1[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:15][c:14]2[n:13][c:9]([C:10](=[O:11])[OH:12])[cH:8]1.ClP(Cl)(Cl)(Cl)[Cl:7]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([Cl:7])[cH:8][c:9]([C:10](=[O:11])[OH:12])[n:13][c:14]2[cH:15]1 | Cc1ccc2c(O)cc(C(=O)O)nc2c1.ClP(Cl)(Cl)(Cl)Cl | Cc1ccc2c(Cl)cc(C(=O)O)nc2c1 | null | null | O=P(Cl)(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_Other | 27014e1419adc48e7dd5f2024d7f933bb85e42d4ec6c57e509da2884d477d689 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc2ncccc2c1 | Cl-P(-Cl)(-Cl)(-Cl)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[#7;a:8]:[c:9](:[c:10]):[c:11]:1:[c:12]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[C:5](=[O;D1;H0:6])-[O;D1;H1:7]):[#7;a:8]:[c:9](:[c:10]):[c:11]:1:[c:12] | 50 | [{"value": 50.0, "product": "C(=O)(O)C1=NC2=CC(=CC=C2C(=C1)Cl)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.2, "product": "C(=O)(O)C1=NC2=CC(=CC=C2C(=C1)Cl)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | null | null | To 20 mL POCl3 was added 2-carboxy-7-methyl-4-hydroxyquinoline (2.5 g, 12.3 mmol) and PCl5 (11.5 g, 55 mmol). The mixture was heated to 130° C. for 3 hours. The reaction mixture was cooled and poured onto ice. The solution was neutralized with solid NaOH and adjusted to pH 11 with solid KOH. The tan precipitate was fil... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | O=P(Cl)(Cl)Cl | 130 | null | Cc1ccc2c(O)cc(C(=O)O)nc2c1.ClP(Cl)(Cl)(Cl)Cl>O=P(Cl)(Cl)Cl>Cc1ccc2c(Cl)cc(C(=O)O)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3b8414190c404782927a055505deeae4 | CCCCC[C@H](O)/C=C/[C@H]1C(=O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O>>CCCCC[C@H](O)/C=C/[C@H]1C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O | C(C(CO)(CO)N)O.Cl.[Mg+2].[Cl-].[Cl-].CCCCC[C@@H](/C=C/[C@@H]1[C@H]([C@H](CC1=O)O)C/C=C/CCCC(=O)O)O>>CCCCC[C@@H](/C=C/[C@@H]1[C@H]([C@H](CC1=O)O)C/C=C\CCCC(=O)O)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:7])/[CH:8]=[CH:9]/[C@H:10]1[C:11](=[O:12])[CH2:13][C@H:14]([OH:15])[C@@H:16]1[CH2:17]/[CH:18]=[CH:19]/[CH2:20][CH2:21][CH2:22][C:23](=[O:24])[OH:25]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([OH:7])/[CH:8]=[CH:9]/[C@H:10]1[C:11](=[O:12])[CH2:13][C@H:14]([OH:15])[C@@H:16]... | CCCCC[C@H](O)/C=C/[C@H]1C(=O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O | CCCCC[C@H](O)/C=C/[C@H]1C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1CCCC1 | null | null | [] | null | null | null | null | To a binding-reaction solution (50 mM Tris/HCl, pH 7.4, 5 mM MgCl2) (0.2 ml) were added the human platelet membrane fraction (0.1 mg) and 5 nM [3H]PGD2 (115 Ci/mmol), and the mixture was reacted at 4° C. for 90 min. After the reaction, the mixture was filtered through a glass fiber filter paper and washed several times... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | C1CCCC1 | null | null | null | null | CCCCC[C@H](O)/C=C/[C@H]1C(=O)C[C@H](O)[C@@H]1C/C=C/CCCC(=O)O>>CCCCC[C@H](O)/C=C/[C@H]1C(=O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d902f388819647f19c93534fd4a3ba09 | O=C(O)c1cccc2[nH]ccc12.c1ccc(CCN2CCNCC2)cc1>>Cl.O=C(c1cccc2[nH]ccc12)N1CCN(CCc2ccccc2)CC1 | C(=O)(O)C1=C2C=CNC2=CC=C1.[I-].ClC1=[N+](C=CC=C1)C.C(CC1=CC=CC=C1)N1CCNCC1.C(C)N(C(C)C)C(C)C>>Cl.N1C=CC2=C(C=CC=C12)C(=O)N1CCN(CC1)CCC1=CC=CC=C1 | O[C:3](=[O:2])[c:4]1[cH:5][cH:6][cH:7][c:8]2[nH:9][cH:10][cH:11][c:12]12.[NH:13]1[CH2:14][CH2:15][N:16]([CH2:17][CH2:18][c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[CH2:25][CH2:26]1>>[ClH:1].[O:2]=[C:3]([c:4]1[cH:5][cH:6][cH:7][c:8]2[nH:9][cH:10][cH:11][c:12]12)[N:13]1[CH2:14][CH2:15][N:16]([CH2:17][CH2:18][c:19]2[cH:2... | O=C(O)c1cccc2[nH]ccc12.c1ccc(CCN2CCNCC2)cc1 | Cl.O=C(c1cccc2[nH]ccc12)N1CCN(CCc2ccccc2)CC1 | null | null | CC(=O)C.CN1C(CCC1)=O | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cccc2[nH]ccc12)N1CCN(CCc2ccccc2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1):[c:4] | 100.1 | [{"value": 100.1, "product": "Cl.N1C=CC2=C(C=CC=C12)C(=O)N1CCN(CC1)CCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of 2.0 g of 4-carboxyindole and 8.1 g of 2-chloro-1-methylpyridinium iodide in 60 ml of N-methylpyrrolidone (NMP) is treated with a solution of 2.36 g of 4-phenethylpiperazine and 8.2 g of ethyldi-isopropylamine (EDIPA) in 20 ml of NMP and subsequently stirred at room temperature for 3 hours. The mixture is ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.c1ccccc1 | null | CC(=O)C.CN1C(CCC1)=O | null | 3 | O=C(O)c1cccc2[nH]ccc12.c1ccc(CCN2CCNCC2)cc1>CC(=O)C.CN1C(CCC1)=O>Cl.O=C(c1cccc2[nH]ccc12)N1CCN(CCc2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a9969a0f2f7a4f47a1fe7d91077a1b28 | CC(C)(C)OC(=O)CN.CC(C)(C)OC(=O)N[C@@H](C(=O)N1CCC[C@H]1C(=O)NCc1cc(Cl)ccc1OCC(=O)O)C1CCCCC1>>O=C1COc2ccc(Cl)cc2CNC(=O)[C@@H]2CCCN2C(=O)[C@@H](C2CCCCC2)NC(=O)CN1 | C(C)N(CC)CC.C1=CC2=C(N=C1)N(N=N2)O.C(CCl)Cl.C(C)(C)(C)OC(=O)N[C@@H](C(=O)N1[C@@H](CCC1)C(=O)NCC1=C(OCC(=O)O)C=CC(=C1)Cl)C1CCCCC1.Cl.C(C)(C)(C)OC(CN)=O.C(C)N(CC)CC.C1=CC2=C(N=C1)N(N=N2)O.C(CCl)Cl>>ClC=1C=CC2=C(CNC([C@H]3N(C([C@H](NC(CNC(CO2)=O)=O)C2CCCCC2)=O)CCC3)=O)C1 | CC(C)(C)OC(=O)[CH2:33][NH2:34].CC(C)(C)O[C:31]([NH:30][C@@H:23]([C:21]([N:20]1[C@H:16]([C:14]([NH:13][CH2:12][c:11]2[c:5]([O:4][CH2:3][C:2](O)=[O:1])[cH:6][cH:7][c:8]([Cl:9])[cH:10]2)=[O:15])[CH2:17][CH2:18][CH2:19]1)=[O:22])[CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1)=[O:32]>>[O:1]=[C:2]1[CH2:3][O:4][c:5]2[cH:6]... | CC(C)(C)OC(=O)CN.CC(C)(C)OC(=O)N[C@@H](C(=O)N1CCC[C@H]1C(=O)NCc1cc(Cl)ccc1OCC(=O)O)C1CCCCC1 | O=C1COc2ccc(Cl)cc2CNC(=O)[C@@H]2CCCN2C(=O)[C@@H](C2CCCCC2)NC(=O)CN1 | null | null | CCOC(=O)C.CN(C)C=O | Acylation | OtherReaction | 83b0767af68fd0802922a9e68b7484d54e581619eb5999fd6f900bb465811e37 | 85da09e33e9583b0a99af5e7800e74daa2c29830b7d9fcb9564274881dd8af16 | O=C1COc2ccccc2CNC(=O)[C@@H]2CCCN2C(=O)[C@@H](C2CCCCC2)NC(=O)CN1 | C-C(-C)(-C)-O-C(=O)-[CH2;D2;+0:1]-[NH2;D1;+0:2].C-C(-C)(-C)-O-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#7:5]-[C:6]-[C:7](-[#7:8])=[O;D1;H0:9].O-[C;H0;D3;+0:10](=[O;D1;H0:11])-[C:12]-[#8:13]>>[#7:8]-[C:7](=[O;D1;H0:9])-[C:6]-[#7:5]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[CH2;D2;+0:1]-[NH;D2;+0:2]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[C:12]-[#8:13... | null | [] | 0 | CELSIUS | 30 | MINUTE | To a solution of 0.049 g (0.09 mmol) [2-({[((2S)-1-{(2R)-2-[(tert-butoxycarbonyl) amino]-2-cyclohexylethanoyl} pyrrolidin-2-yl)carbonyl]amino} methyl)-4-chlorophenoxy]acetic acid (J. Med. Chem 1998, 41, 3210) in 3 mL DMF was added 0.018 g (0.1 mmol) glycine tertbutyl ester hydrochloride, 0.015 mL (0.1 mmol) triethylami... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ester.Ether.Primary amine.Boc.Boc | Secondary amide.Secondary amide | null | c1ccc2c(c1)CNC[C@@H]1CCCN1CCNCCNCCO2 | c1ccc2c(c1)CNC[C@@H]1CCCN1CCNCCNCCO2.C1CCCCC1 | HO- | CCOC(=O)C.CN(C)C=O | 0 | 0.5 | CC(C)(C)OC(=O)CN.CC(C)(C)OC(=O)N[C@@H](C(=O)N1CCC[C@H]1C(=O)NCc1cc(Cl)ccc1OCC(=O)O)C1CCCCC1>CCOC(=O)C.CN(C)C=O>O=C1COc2ccc(Cl)cc2CNC(=O)[C@@H]2CCCN2C(=O)[C@@H](C2CCCCC2)NC(=O)CN1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a34b72d6641642e8a67a6948726a049e | CCOC(=O)C[N+](=O)[O-].Cn1c(=O)oc(=O)c2ccccc21>>Cn1c(=O)c([N+](=O)[O-])c(O)c2ccccc21 | CN1C=2C(C(=O)OC1=O)=CC=CC2.Cl.C(C)OC(C[N+](=O)[O-])=O.[H-].[Na+].[H][H]>>OC1=C(C(N(C2=CC=CC=C12)C)=O)[N+](=O)[O-] | CCOC(=O)[CH2:5][N+:6](=[O:7])[O-:8].o1[c:3](=[O:4])[n:2]([CH3:1])[c:16]2[c:11]([c:9]1=[O:10])[cH:12][cH:13][cH:14][cH:15]2>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]([N+:6](=[O:7])[O-:8])[c:9]([OH:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12 | CCOC(=O)C[N+](=O)[O-].Cn1c(=O)oc(=O)c2ccccc21 | Cn1c(=O)c([N+](=O)[O-])c(O)c2ccccc21 | null | null | CC(=O)N(C)C | Miscellaneous | OtherReaction | 9f1cd067fb92ced8282918750f12d3f893b171f52d5440877d69c42079cef3af | aae580ef2b02838387dafe741a7f7280f903f5ce71ca5dcea45fbd2f70cde3b8 | O=c1ccc2ccccc2[nH]1 | C-C-O-C(=O)-[CH2;D2;+0:1]-[#7;+:2](-[O;-;D1;H0:3])=[O;D1;H0:4].[C;D1;H3:5]-[#7;a:6]1:[c:7](:[c:8]):[c:9](:[c:10]):[c;H0;D3;+0:11](=[O;H0;D1;+0:12]):o:[c;H0;D3;+0:13]:1=[O;D1;H0:14]>>[C;D1;H3:5]-[#7;a:6]1:[c:7](:[c:8]):[c:9](:[c:10]):[c;H0;D3;+0:11](-[OH;D1;+0:12]):[c;H0;D3;+0:1](-[#7;+:2](-[O;-;D1;H0:3])=[O;D1;H0:4]):[... | 27 | [{"value": 27.0, "product": "OC1=C(C(N(C2=CC=CC=C12)C)=O)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.9, "product": "OC1=C(C(N(C2=CC=CC=C12)C)=O)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A solution of ethylnitroacetate (15.96 g, 120 mmol) was added slowly in a suspension of sodium hydride (60% in mineral oil, 5.28 g, 132 mmol) in dimethylacetamide under N2 atmosphere. The mixture was allowed to stir at room temperature until the evolution of hydrogen gas ceased, then heated to 90° C. for 30 min. and co... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group | Nitro group.Aromatic alcohol | c1nc2ccccc2co1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | CC(=O)N(C)C | 90 | null | CCOC(=O)C[N+](=O)[O-].Cn1c(=O)oc(=O)c2ccccc21>CC(=O)N(C)C>Cn1c(=O)c([N+](=O)[O-])c(O)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e54e6113600045fa9609df769f8eb552 | CC(C)(C)OC(=O)N1CCNCC1.O=C(Cl)c1cccs1>>CC(C)(C)OC(=O)N1CCN(C(=O)c2cccs2)CC1 | S1C(=CC=C1)C(=O)Cl.C(C)(C)(C)OC(=O)N1CCNCC1>>C(C)(C)(C)OC(=O)N1CCN(CC1)C(=O)C=1SC=CC1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:19][CH2:20]1.Cl[C:12](=[O:13])[c:14]1[cH:15][cH:16][cH:17][s:18]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][cH:17][s:18]2)[CH2:19][CH2:20]1 | CC(C)(C)OC(=O)N1CCNCC1.O=C(Cl)c1cccs1 | CC(C)(C)OC(=O)N1CCN(C(=O)c2cccs2)CC1 | null | CN(C)C=1C=CN=CC1 | N1=CC=CC=C1 | Acylation | N-alkylation of secondary amines with alkyl halides | 008ee4368afbd52034630a2410a1738f53049b314574435184e4e0be81b96642 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1cccs1)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[#7:7]-[C:8]-[C:9]-1)-[c:3](:[c:4]):[#16;a:5]:[c:6] | 88.1 | [{"value": 88.0, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C(=O)C=1SC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.1, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C(=O)C=1SC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 2-Thiophenecarbonylchloride (2.04 g, 1.49 mL) was added to a solution of tertbutyl-1-piperazinecarboxylate (2.5 g, 13.4 mmol) and DMAP (20 mg) in pyridine (15 mL) at 0° C. under N2 atmosphere and stirred at room temperature for overnight. The mixture was poured into ice water, the precipitate was filtered, washed sever... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccsc1 | HCl | CN(C)C=1C=CN=CC1.N1=CC=CC=C1 | null | 8 | CC(C)(C)OC(=O)N1CCNCC1.O=C(Cl)c1cccs1>CN(C)C=1C=CN=CC1.N1=CC=CC=C1>CC(C)(C)OC(=O)N1CCN(C(=O)c2cccs2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-303d0064dc364a3489dbbedaa84ff1ac | CCOC(=O)CBr.Cc1ccc(S)cc1>>CCOC(=O)CSc1ccc(C)cc1 | CC1=CC=C(C=C1)S.[H-].[Na+].C(C)OC(CBr)=O>>C(C)OC(CSC1=CC=C(C=C1)C)=O | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[SH:7][c:8]1[cH:9][cH:10][c:11]([CH3:12])[cH:13][cH:14]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][S:7][c:8]1[cH:9][cH:10][c:11]([CH3:12])[cH:13][cH:14]1 | CCOC(=O)CBr.Cc1ccc(S)cc1 | CCOC(=O)CSc1ccc(C)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | thioether_nucl_sub | f166e7385b573c9a16b8c0c50fdc295f5ffeb93ca128b039715b5275a6d52d4d | d03e1aefd322fd7bd17b31466f3c805b76027422225d66386ab24abbd950f9cb | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[SH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[S;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 99 | [{"value": 99.0, "product": "C(C)OC(CSC1=CC=C(C=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 4-methylbenzenethiol (5 g, 40.25) in dry THF was added dropwise to a suspension of NaH (60% in mineral oil, 1.98 g, 48.30) in THF at room temperature and stirred for 30 min. under N2 atmosphere. Ethylbromoacetate (4.9 mL, 44.27) was added slowly to this solution and further stirred at room temperature for... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic thiol | Ester.Monosulfide | null | null | c1ccccc1 | HBr | C1CCOC1 | null | 0.5 | CCOC(=O)CBr.Cc1ccc(S)cc1>C1CCOC1>CCOC(=O)CSc1ccc(C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-157b7894b4f7449aa2714755436d2131 | CCOC(=O)CS(C)(=O)=O.Cn1c(=O)oc(=O)c2ccccc21>>Cn1c(=O)c(S(C)(=O)=O)c(O)c2ccccc21 | CN1C=2C(C(=O)OC1=O)=CC=CC2.Cl.C(C)OC(CS(=O)(=O)C)=O.[H-].[Na+].[H][H]>>OC1=C(C(N(C2=CC=CC=C12)C)=O)S(=O)(=O)C | CCOC(=O)[CH2:5][S:6]([CH3:7])(=[O:8])=[O:9].o1[c:3](=[O:4])[n:2]([CH3:1])[c:17]2[c:12]([c:10]1=[O:11])[cH:13][cH:14][cH:15][cH:16]2>>[CH3:1][n:2]1[c:3](=[O:4])[c:5]([S:6]([CH3:7])(=[O:8])=[O:9])[c:10]([OH:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12 | CCOC(=O)CS(C)(=O)=O.Cn1c(=O)oc(=O)c2ccccc21 | Cn1c(=O)c(S(C)(=O)=O)c(O)c2ccccc21 | null | null | CC(=O)N(C)C | Miscellaneous | OtherReaction | 042875996d4215dc9e65184856fc80d10a90192b316c743b0fd800738b01cbe8 | 09cbafc950d6dd58e2d039683f7feb9653b73be50bd602d93d736eaefecf29c6 | O=c1ccc2ccccc2[nH]1 | C-C-O-C(=O)-[CH2;D2;+0:1]-[#16:2](-[C;D1;H3:3])(=[O;D1;H0:4])=[O;D1;H0:5].[C;D1;H3:6]-[#7;a:7]1:[c:8](:[c:9]):[c:10](:[c:11]):[c;H0;D3;+0:12](=[O;H0;D1;+0:13]):o:[c;H0;D3;+0:14]:1=[O;D1;H0:15]>>[C;D1;H3:6]-[#7;a:7]1:[c:8](:[c:9]):[c:10](:[c:11]):[c;H0;D3;+0:12](-[OH;D1;+0:13]):[c;H0;D3;+0:1](-[#16:2](-[C;D1;H3:3])(=[O;... | 48 | [{"value": 48.0, "product": "OC1=C(C(N(C2=CC=CC=C12)C)=O)S(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.9, "product": "OC1=C(C(N(C2=CC=CC=C12)C)=O)S(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A solution of ethylmethanesulfonylacetate (3.78 g, 22.74 mmol) was added slowly in a suspension of sodium hydride (60% in mineral oil, 1.07 g, 25 mmol) in dimethylacetamide under N2 atmosphere. The mixture was allowed to stir at room temperature until the evolution of hydrogen gas ceased, then heated to 90° C. for 30 m... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aromatic alcohol | c1nc2ccccc2co1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | CC(=O)N(C)C | 90 | null | CCOC(=O)CS(C)(=O)=O.Cn1c(=O)oc(=O)c2ccccc21>CC(=O)N(C)C>Cn1c(=O)c(S(C)(=O)=O)c(O)c2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5e984f0bb90a49f49c73a342593a21ea | CCC(CC)(C(=O)[O-])C(=O)[O-].O=c1[nH]c2ccccc2c(=O)o1>>CCOC(=O)c1c(O)c2ccccc2[nH]c1=O | C1=2C(=O)OC(NC1=CC=CC2)=O.CC(=O)N(C)C.Cl.C(C)C(C(=O)[O-])(C(=O)[O-])CC.[H-].[Na+].CC(=O)N(C)C.[H][H]>>C(C)OC(=O)C=1C(NC2=CC=CC=C2C1O)=O | CC[C:6](C(=O)[O-])([CH2:2][CH3:1])[C:4]([O-:3])=[O:5].o1[c:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[nH:15][c:16]1=[O:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([OH:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[nH:15][c:16]1=[O:17] | CCC(CC)(C(=O)[O-])C(=O)[O-].O=c1[nH]c2ccccc2c(=O)o1 | CCOC(=O)c1c(O)c2ccccc2[nH]c1=O | null | null | null | Protection | OtherReaction | 55a26eee32bed0eb795bc5197612c7390d9e3783c834a724afe5b2c38f6037bd | a8bb12d6e1c9c61f6e4997a40a83164abba682d53cbe433a81ee496453916abf | O=c1ccc2ccccc2[nH]1 | C-C-[C;H0;D4;+0:1](-[CH2;D2;+0:2]-[C;D1;H3:3])(-C(=O)-[O-])-[C:4](-[O-;H0;D1:5])=[O;D1;H0:6].[O;D1;H0:7]=[c;H0;D3;+0:8]1:[#7;a:9]:[c:10](:[c:11]):[c:12](:[c:13]):[c;H0;D3;+0:14](=[O;H0;D1;+0:15]):o:1>>[C;D1;H3:3]-[CH2;D2;+0:2]-[O;H0;D2;+0:5]-[C:4](=[O;D1;H0:6])-[c;H0;D3;+0:1]1:[c;H0;D3;+0:8](=[O;D1;H0:7]):[#7;a:9]:[c:1... | 47 | [{"value": 47.0, "product": "C(C)OC(=O)C=1C(NC2=CC=CC=C2C1O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A solution of diethylmalonate (80 g, 0.50 mol) was added slowly to a suspension of sodium hydride (60% in mineral oil, 22 g, 0.55 mol) in dimethylacetamide under N2 atmosphere. The mixture was allowed to stir at room temperature until the evolution of hydrogen gas ceased, then heated to 90° C. for 30 min. and cooled to... | 10.6084/m9.figshare.5104873.v1 | null | null | Ester.Aromatic alcohol | c1nc2ccccc2co1 | c1cnc2ccccc2c1 | c1cnc2ccccc2c1 | HO- | null | 90 | null | CCC(CC)(C(=O)[O-])C(=O)[O-].O=c1[nH]c2ccccc2c(=O)o1>>CCOC(=O)c1c(O)c2ccccc2[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-697eb1beb35a4059a73112f3071f16a1 | CCOC(=O)C(F)(F)F.CSc1ccc(C(C)=O)cc1>>CSc1ccc(C(=O)CC(=O)C(F)(F)F)cc1 | CC(=O)C1=CC=C(C=C1)SC.FC(C(=O)OCC)(F)F.C[O-].[Na+].CO.Cl>>FC(C(CC(=O)C1=CC=C(C=C1)SC)=O)(F)F | CCO[C:10](=[O:11])[C:12]([F:13])([F:14])[F:15].[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH3:9])[cH:16][cH:17]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH2:9][C:10](=[O:11])[C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1 | CCOC(=O)C(F)(F)F.CSc1ccc(C(C)=O)cc1 | CSc1ccc(C(=O)CC(=O)C(F)(F)F)cc1 | null | null | CC(C)(C)OC | C-C Coupling | OtherReaction | 32688b2be78fcb1623f924ded4f1da30562c8a1cc17a29844013a0b12a85add5 | da4745a356290ddd7ef0372302b86253afded9b0422422979166627a7dfa5740 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;D1;H0:6].[CH3;D1;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]>>[F;D1;H0:4]-[C:3](-[F;D1;H0:5])(-[F;D1;H0:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10] | 71 | [{"value": 71.0, "product": "FC(C(CC(=O)C1=CC=C(C=C1)SC)=O)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of ethyl trifluoroacetate (7.95 ml, 1.1 eq) in MTBE (125 ml) was added dropwise 25% sodium methoxide in methanol (16 ml, 1.2 eq). 4-Methylthioacetophenone (Aldrich, 10 g, 0.06 mol) was added portionwise and the mixture stirred at ambient temperature overnight. 2N Hydrochloric acid (40 ml) was added cautio... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone.Ketone | null | null | c1ccccc1 | HO- | CC(C)(C)OC | null | 8 | CCOC(=O)C(F)(F)F.CSc1ccc(C(C)=O)cc1>CC(C)(C)OC>CSc1ccc(C(=O)CC(=O)C(F)(F)F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e51691821d1c445ea36ecbddd8c1bb23 | CSC(=N)N.CSc1ccc(C(=O)CC(=O)C(F)(F)F)cc1>>CSc1ccc(-c2cc(C(F)(F)F)nc(SC)n2)cc1 | FC(C(CC(=O)C1=CC=C(C=C1)SC)=O)(F)F.S(=O)(=O)(O)O.CSC(N)=N.C(C)(=O)[O-].[Na+]>>CSC1=NC(=CC(=N1)C1=CC=C(C=C1)SC)C(F)(F)F | [NH2:14][C:15]([S:16][CH3:17])=[NH:18].O=[C:7]([c:6]1[cH:5][cH:4][c:3]([S:2][CH3:1])[cH:20][cH:19]1)[CH2:8][C:9](=O)[C:10]([F:11])([F:12])[F:13]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[n:14][c:15]([S:16][CH3:17])[n:18]2)[cH:19][cH:20]1 | CSC(=N)N.CSc1ccc(C(=O)CC(=O)C(F)(F)F)cc1 | CSc1ccc(-c2cc(C(F)(F)F)nc(SC)n2)cc1 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | e0331cabf8af13e5ec1457818b490434f9c26c5e26a948260b8ee78b7713c471 | 3f075207051648b96e612088db00199801a7e1bc3915759039d76cbd15758a8b | c1ccc(-c2ccncn2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=O)-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12].[C;D1;H3:13]-[#16:14]-[C;H0;D3;+0:15](-[NH2;D1;+0:16])=[NH;D1;+0:17]>>[C;D1;H3:13]-[#16:14]-[c;H0;D3;+0:15]1:[n;H0;D2;+0:16]:[c;H0;D3;+0:3](-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;... | 96.2 | [{"value": 96.2, "product": "CSC1=NC(=CC(=N1)C1=CC=C(C=C1)SC)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 4,4,4-trifluoro-1-[4-(methylthio)phenyl]butane-1,3-dione (5 g) and 2-methyl-2-thiopseudourea sulfate (5.1 g, 0.98 eq) in acetic acid (100 ml) was added sodium acetate (3 g, 2 eq) and heated under reflux for 8 h. The mixture was concentrated in vacuo and water (100 ml) added to give a solid, which was is... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine.Monosulfide | Monosulfide | null | c1cncnc1 | c1ccccc1.c1cncnc1 | HO- | C(C)(=O)O | null | null | CSC(=N)N.CSc1ccc(C(=O)CC(=O)C(F)(F)F)cc1>C(C)(=O)O>CSc1ccc(-c2cc(C(F)(F)F)nc(SC)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-32e67c2966e547bfa9726d4db0b83282 | CSc1ccc(B(O)O)cc1.CSc1nc(Cl)cc(C(F)(F)F)n1>>CSc1ccc(-c2cc(C(F)(F)F)nc(SC)n2)cc1 | ClC1=NC(=NC(=C1)C(F)(F)F)SC.CSC1=CC=C(C=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>CSC1=NC(=CC(=N1)C1=CC=C(C=C1)SC)C(F)(F)F | OB(O)[c:6]1[cH:5][cH:4][c:3]([S:2][CH3:1])[cH:20][cH:19]1.Cl[c:7]1[cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[n:14][c:15]([S:16][CH3:17])[n:18]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[n:14][c:15]([S:16][CH3:17])[n:18]2)[cH:19][cH:20]1 | CSc1ccc(B(O)O)cc1.CSc1nc(Cl)cc(C(F)(F)F)n1 | CSc1ccc(-c2cc(C(F)(F)F)nc(SC)n2)cc1 | null | null | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 5efc69cb0f56c6c241a71b9df28c03b094ed8fc2f31567997f12f88c03083478 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccncn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6](-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[F;D1;H0:10]):[c:11]:1.O-B(-O)-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[#16:4]-[c:3]1:[#7;a:5]:[c:6](-[C:7](-[F;D1;H0:8])(-[F;D1;H0:9])-[F;D1;H0:10]):[c:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16])... | 84 | [{"value": 84.0, "product": "CSC1=NC(=CC(=N1)C1=CC=C(C=C1)SC)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A mixture of 4-chloro-2-methylthio-6-(trifluoromethyl)pyrimidine (ButtPark Ltd, 2.86 g, 14.55 mmol), 4-(methylthio)phenylboronic acid (Aldrich, 2.83 g, 1.1 eq), tetrakistriphenylphosphine palladium (0) (0.2 g) and sodium carbonate (4.04 g, 2.6 eq) in DME (200 ml) and water (100 ml) was heated under reflux with stirring... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1 | c1ccccc1.c1cncnc1 | HCl.B | O.COCCOC | null | 24 | CSc1ccc(B(O)O)cc1.CSc1nc(Cl)cc(C(F)(F)F)n1>O.COCCOC>CSc1ccc(-c2cc(C(F)(F)F)nc(SC)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-17ed47ef835b4d92b99869f4520b7108 | CS(=O)(=O)c1ccc(-c2cc(C(F)(F)F)nc(S(C)(=O)=O)n2)cc1.NC1CCOCC1>>CS(=O)(=O)c1ccc(-c2cc(C(F)(F)F)nc(NC3CCOCC3)n2)cc1 | O.CS(=O)(=O)C1=NC(=CC(=N1)C1=CC=C(C=C1)S(=O)(=O)C)C(F)(F)F.O1CCC(CC1)N>>CS(=O)(=O)C1=CC=C(C=C1)C1=NC(=NC(=C1)C(F)(F)F)NC1CCOCC1 | CS(=O)(=O)[c:17]1[n:16][c:11]([C:12]([F:13])([F:14])[F:15])[cH:10][c:9](-[c:8]2[cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:27][cH:26]2)[n:25]1.[NH2:18][CH:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[n:16][c:17... | CS(=O)(=O)c1ccc(-c2cc(C(F)(F)F)nc(S(C)(=O)=O)n2)cc1.NC1CCOCC1 | CS(=O)(=O)c1ccc(-c2cc(C(F)(F)F)nc(NC3CCOCC3)n2)cc1 | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | OtherReaction | 289adcacbe89f1503fb3c9d1b660927aaeb421d7b5520077738f22dce3010144 | f263fb011eaf2f85af25e2af9b0908fb2797226f3495a5d6be9230bf229d4fae | c1ccc(-c2ccnc(NC3CCOCC3)n2)cc1 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9]>>[C:6]-[C:7](-[NH;D2;+0:8]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5])-[C:9] | 40 | [{"value": 40.0, "product": "CS(=O)(=O)C1=CC=C(C=C1)C1=NC(=NC(=C1)C(F)(F)F)NC1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.6, "product": "CS(=O)(=O)C1=CC=C(C=C1)C1=NC(=NC(=C1)C(F)(F)F)NC1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2-(methylsulfonyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyrimidine (0.277 g, 0.73 mmol) in N-methylpyrrolidone (1.25 ml) was added tetrahydro-2H-pyran-4-amine (0.147 g, 2 eq.), the mixture was stirred for 1 hour and then water (1.25 ml) was added dropwise. This resulted in a precipitate bein... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfone | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.C1CCOCC1 | HO- | CN1C(CCC1)=O | null | 1 | CS(=O)(=O)c1ccc(-c2cc(C(F)(F)F)nc(S(C)(=O)=O)n2)cc1.NC1CCOCC1>CN1C(CCC1)=O>CS(=O)(=O)c1ccc(-c2cc(C(F)(F)F)nc(NC3CCOCC3)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7489cadc00124f82a4089f651da7299f | CI.CS(=O)(=O)c1ccc(-c2cc(C(F)(F)F)nc(NC3CCOCC3)n2)cc1>>CN(c1nc(-c2ccc(S(C)(=O)=O)cc2)cc(C(F)(F)F)n1)C1CCOCC1 | IC.CS(=O)(=O)C1=CC=C(C=C1)C1=NC(=NC(=C1)C(F)(F)F)NC1CCOCC1.[H-].[Na+]>>CS(=O)(=O)C1=CC=C(C=C1)C1=NC(=NC(=C1)C(F)(F)F)N(C1CCOCC1)C | I[CH3:1].[NH:2]([c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[cH:14][cH:15]2)[cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[n:22]1)[CH:23]1[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1>>[CH3:1][N:2]([c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([S:10]([CH3:11])(=[O:12])=[O:13])[cH:14][cH:15]2)[cH:16][c... | CI.CS(=O)(=O)c1ccc(-c2cc(C(F)(F)F)nc(NC3CCOCC3)n2)cc1 | CN(c1nc(-c2ccc(S(C)(=O)=O)cc2)cc(C(F)(F)F)n1)C1CCOCC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e1587a52a1bca6a80c6048d43276d8bccf8d3e94e692e6b210e5fd3b22494187 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(-c2ccnc(NC3CCOCC3)n2)cc1 | I-[CH3;D1;+0:1].[C:2]-[C:3](-[NH;D2;+0:4]-[c:5](:[#7;a:6]:[c:7]):[#7;a:8]:[c:9])-[C:10]>>[C:2]-[C:3](-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[c:5](:[#7;a:6]:[c:7]):[#7;a:8]:[c:9])-[C:10] | null | [] | null | null | 30 | MINUTE | A solution of 4-[4-(methylsulfonyl)phenyl]-N-tetrahydro-2H-pyran-4-yl-6-(trifluoromethyl)pyrimidin-2-amine (0.05 g) in dry dimethylformamide (2 ml) was treated with sodium hydride (0.007 g, 60% in mineral oil) and the mixture stirred at ambient temperature for 30 minutes. Iodomethane (0.01 ml) was added and the mixture... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | null | null | c1cncnc1.c1ccccc1.C1CCOCC1 | HI | CN(C=O)C | null | 0.5 | CI.CS(=O)(=O)c1ccc(-c2cc(C(F)(F)F)nc(NC3CCOCC3)n2)cc1>CN(C=O)C>CN(c1nc(-c2ccc(S(C)(=O)=O)cc2)cc(C(F)(F)F)n1)C1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e47f298713b0429db9879ef8101f178d | COC(=O)c1cccc2[nH]ccc12>>OCc1cccc2[nH]ccc12 | [H-].[Al+3].[Li+].[H-].[H-].[H-].N1C=CC=2C(=CC=CC12)C(=O)OC>>OCC1=C2C=CNC2=CC=C1 | CO[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][c:7]2[nH:8][cH:9][cH:10][c:11]12>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[nH:8][cH:9][cH:10][c:11]12 | COC(=O)c1cccc2[nH]ccc12 | OCc1cccc2[nH]ccc12 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc2[nH]ccc2c1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:4] | 99.9 | [{"value": 99.0, "product": "OCC1=C2C=CNC2=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.9, "product": "OCC1=C2C=CNC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a mixture of lithium aluminum hydride (1.3 g, 34 mmol) in THF (200 mL), methyl 4-indole carboxylate (3.0 g, 17 mmol) in THF (100 mL) was added dropwise at room temperature. The reaction mixture was stirred at room temperature for 2 h and then quenched with ethyl acetate. The mixture was treated with water (1.3 mL), ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2[nH]ccc2c1 | Other | C1CCOC1 | null | 2 | COC(=O)c1cccc2[nH]ccc12>C1CCOC1>OCc1cccc2[nH]ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1c6c6e178aac4e5f90f9df9b818dcfd8 | OCc1cccc2[nH]ccc12>>O=Cc1cccc2[nH]ccc12 | OCC1=C2C=CNC2=CC=C1.C[N+]1(CCOCC1)[O-]>>N1C=CC=2C(=CC=CC12)C=O | [OH:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[nH:8][cH:9][cH:10][c:11]12>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[nH:8][cH:9][cH:10][c:11]12 | OCc1cccc2[nH]ccc12 | O=Cc1cccc2[nH]ccc12 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc2[nH]ccc2c1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[CH2;D2;+0:5]-[OH;D1;+0:6]):[c:7]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6]):[c:7] | 81 | [{"value": 80.0, "product": "N1C=CC=2C(=CC=CC12)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.0, "product": "N1C=CC=2C(=CC=CC12)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Tetrapropylammonium perruthenate (0.3 g, 0.85 mmol) was added in portions to a mixture of alcohol product from Step A (2.5 g, 17 mmol), N-methylmorpholine N-oxide (3.0 g, 25 mmol) and 4 A molecular sieves (3.0 g) in anhydrous methylene chloride (30 mL) at room temperature. The mixture was stirred at room temperature un... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccc2[nH]ccc2c1 | null | [Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.C(Cl)Cl | null | 1 | OCc1cccc2[nH]ccc12>[Ru](=O)(=O)(=O)[O-].C(CC)[N+](CCC)(CCC)CCC.C(Cl)Cl>O=Cc1cccc2[nH]ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-93083a9cf6604e6bb51a43977e057e85 | CN.O=Cc1cccc2[nH]ccc12>>NCc1cccc2[nH]ccc12 | N1C=CC=2C(=CC=CC12)C=O.O.CN.[BH4-].[Na+]>>NCC1=C2C=CNC2=CC=C1 | C[NH2:1].O=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[nH:8][cH:9][cH:10][c:11]12>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]2[nH:8][cH:9][cH:10][c:11]12 | CN.O=Cc1cccc2[nH]ccc12 | NCc1cccc2[nH]ccc12 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | d1a2545f3ec8db93b95967f7fae0eb0e5c148e57b578d5531dc41fef9bdc2fb0 | 65268f180191aacdedd4dc283ac42ccdf2bd90f4b1b48e746122cc8cd145fe75 | c1ccc2[nH]ccc2c1 | C-[NH2;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[CH2;D2;+0:2]-[NH2;D1;+0:1]):[c:4] | 88 | [{"value": 88.0, "product": "NCC1=C2C=CNC2=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of aldehyde product from Step B (2.0 g, 14 mmol) in methanol (100 mL), 40% methylamine in water (2.27 mL, 27.6 mmol) was added at room temperature over a period of 10 min. The mixture was stirred at room temperature under nitrogen overnight and then was cooled down to 0° C. Sodium borohydride (1.05 g, 27.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Primary amine | null | null | c1ccc2[nH]ccc2c1 | HO- | CO | null | 8 | CN.O=Cc1cccc2[nH]ccc12>CO>NCc1cccc2[nH]ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-63e285bda9ba407a84ecde47a841fc59 | COC(=O)C(=O)OC.c1ccc2[nH]ccc2c1>>Cn1ccc2ccccc21 | N1C=CC2=CC=CC=C12.C(C(=O)OC)(=O)OC.CC(C)([O-])C.[K+]>>CN1C=CC2=CC=CC=C12 | COC(=O)C(=O)O[CH3:1].[nH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12 | COC(=O)C(=O)OC.c1ccc2[nH]ccc2c1 | Cn1ccc2ccccc21 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-methylation | 45d087e669e7ced2fcca083b9a7995c8ca53d293f4ea7f1924a30828f449e6a8 | 96828a0648495aff2c1f536e3b5314dc763196d4ff5c85c4b65f7a1f616a38fb | c1ccc2[nH]ccc2c1 | C-O-C(=O)-C(=O)-O-[CH3;D1;+0:1].[c:2]:[c:3]1:[c:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[c:3]:1:[c:2] | null | [] | null | null | null | null | To a solution of indole product from Example 38, Step F (182 mg, 0.694 mmol) and dimethyl oxalate (90 mg, 0.76 mmol) in DMF (5 mL), potassium tert-butoxide (86 mg, 0.76 mmol) was added in one portion at room temperature under nitrogen. The reaction mixture was warmed to reflux under nitrogen for 30 min and then was coo... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | O.CN(C)C=O | null | null | COC(=O)C(=O)OC.c1ccc2[nH]ccc2c1>O.CN(C)C=O>Cn1ccc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-86f7c0e993814eafbc2709fb2bf80f41 | CCOC(=O)C(=O)OCC.c1ccc2[nH]ccc2c1>>CCn1ccc2ccccc21 | CC(C)([O-])C.[K+].N1C=CC2=CC=CC=C12.C(C(=O)OCC)(=O)OCC>>C(C)N1C=CC2=CC=CC=C12 | CCOC(=O)C(=O)O[CH2:2][CH3:1].[nH:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]12>>[CH3:1][CH2:2][n:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]12 | CCOC(=O)C(=O)OCC.c1ccc2[nH]ccc2c1 | CCn1ccc2ccccc21 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 45d087e669e7ced2fcca083b9a7995c8ca53d293f4ea7f1924a30828f449e6a8 | 96828a0648495aff2c1f536e3b5314dc763196d4ff5c85c4b65f7a1f616a38fb | c1ccc2[nH]ccc2c1 | C-C-O-C(=O)-C(=O)-O-[CH2;D2;+0:1]-[C;D1;H3:2].[c:3]:[c:4]1:[c:5]:[c:6]:[c:7]:[nH;D2;+0:8]:1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[c:7]:[c:6]:[c:5]:[c:4]:1:[c:3] | null | [] | null | null | null | null | To a solution of indole product in Example 38 (150 mg, 0.572 mmol) and diethyl oxalate (92 mg, 0.63 mmol) in DMF (5 mL), potassium tert-butoxide (71 mg, 0.63 mmol) was added in one portion at room temperature under nitrogen. The reaction mixture was warmed to reflux under nitrogen for 1 h and then was cooled down to ro... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | O.CN(C)C=O | null | null | CCOC(=O)C(=O)OCC.c1ccc2[nH]ccc2c1>O.CN(C)C=O>CCn1ccc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0ba1d7332534476289ac256d67cc7371 | C=O.c1ccc2c(c1)CCN2>>CN1CCc2ccccc21 | C(#N)[BH3-].[Na+].N1CCC2=CC=CC=C12.C(C)(=O)O.C=O>>CN1CCC2=CC=CC=C12 | O=[CH2:1].[NH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]21>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]21 | C=O.c1ccc2c(c1)CCN2 | CN1CCc2ccccc21 | null | null | CO | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | 831ca821d85adad567722fd7fff22eb37d2c95259b7c4e2e50be675464e6c02a | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc2c(c1)CCN2 | O=[CH2;D1;+0:1].[c:2]:[c:3]1:[c:4]-[C:5]-[C:6]-[NH;D2;+0:7]-1>>[CH3;D1;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[c:4]:[c:3]-1:[c:2] | null | [] | null | null | 1 | HOUR | To a solution of the indoline product of Example 42 (110 mg, 0.420 mmol) and acetic acid (0.1 mL) in methanol (4 mL), 37% aqueous formaldehyde (0.04 mL, 0.5 mmol) was added dropwise at room temperature. The reaction mixture was stirred at room temperature under nitrogen for 1 h, and then sodium cyanoborohydride (66 mg,... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | Other | CO | null | 1 | C=O.c1ccc2c(c1)CCN2>CO>CN1CCc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0d4e9f47c44c454597841332d2046dc8 | CN1CCc2ccccc21>>Cn1ccc2ccccc21 | CN1CCC2=CC=CC=C12>>CN1C=CC2=CC=CC=C12 | [CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]21>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12 | CN1CCc2ccccc21 | Cn1ccc2ccccc21 | null | O=[Mn]=O | C1(=CC=CC=C1)C | Oxidation | OtherReaction | e52f71b450655496f3d86d95ebb6e98299f0cbbc99b337ca618ec98c1c63efaa | d04c5715e362fd32bffcfe60290c32ad0adedbe2d4f79a927f35e0b5f372b098 | c1ccc2[nH]ccc2c1 | [C;D1;H3:1]-[N;H0;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]-1:[c:8]>>[C;D1;H3:1]-[n;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c:5](:[c:6]):[c:7]:1:[c:8] | 57 | [{"value": 57.0, "product": "CN1C=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The N-methyl indoline product in Example 47 (70 mg, 0.22 mmol) was dissolved in toluene (9 mL) in a 50-mL flask under N2 fitted with a condenser. MnO2 (199 mg, 2.3 mmol) was added, and the mixture was heated to ref lux for 1.5 h. The mixture was cooled to rt, Celite, and the pad was washed several times with liberal am... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | null | c1ccc2c(c1)CC[NH]2 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | null | O=[Mn]=O.C1(=CC=CC=C1)C | null | null | CN1CCc2ccccc21>O=[Mn]=O.C1(=CC=CC=C1)C>Cn1ccc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6a4156fc35c24ba285b9a00cd2e1360b | C=O.c1ccc2c(c1)CCN2>>CN1CCc2ccccc21 | C=O.N1CCC2=CC=CC=C12.[BH3-]C#N.[Na+]>>CN1CCC2=CC=CC=C12 | O=[CH2:1].[NH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]21>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]21 | C=O.c1ccc2c(c1)CCN2 | CN1CCc2ccccc21 | null | CC(=O)O | CO.C(Cl)Cl | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | 831ca821d85adad567722fd7fff22eb37d2c95259b7c4e2e50be675464e6c02a | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc2c(c1)CCN2 | O=[CH2;D1;+0:1].[c:2]:[c:3]1:[c:4]-[C:5]-[C:6]-[NH;D2;+0:7]-1>>[CH3;D1;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[c:4]:[c:3]-1:[c:2] | 214.5 | [{"value": 87.0, "product": "CN1CCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 214.5, "product": "CN1CCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | The indoline product from Example 47, Step B (16 mg, 0.049 mmol) was dissolved in MeOH (2 mL) in a 25-mL flask under N2. A catalytic amount of HOAc (1 drop) and aqueous formaldehyde (15 μL, 0.15 mmol) were added, and the mixture stirred for 1 h. NaBH3CN (16 mg, 0.25 mmol) was added, and the mixture stirred for an addit... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | Other | CC(=O)O.CO.C(Cl)Cl | null | 1 | C=O.c1ccc2c(c1)CCN2>CC(=O)O.CO.C(Cl)Cl>CN1CCc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b64fdbea791444629cd2b3cbd64f560b | COC(=O)C(=O)OC.c1ccc2[nH]ccc2c1>>Cn1ccc2ccccc21 | N1C=CC2=CC=CC=C12.C(C(=O)OC)(=O)OC.CC(C)([O-])C.[K+]>>CN1C=CC2=CC=CC=C12 | COC(=O)C(=O)O[CH3:1].[nH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12 | COC(=O)C(=O)OC.c1ccc2[nH]ccc2c1 | Cn1ccc2ccccc21 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-methylation | 45d087e669e7ced2fcca083b9a7995c8ca53d293f4ea7f1924a30828f449e6a8 | 96828a0648495aff2c1f536e3b5314dc763196d4ff5c85c4b65f7a1f616a38fb | c1ccc2[nH]ccc2c1 | C-O-C(=O)-C(=O)-O-[CH3;D1;+0:1].[c:2]:[c:3]1:[c:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[c:3]:1:[c:2] | 47 | [{"value": 47.0, "product": "CN1C=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The appropriate indole product prepared using the procedures of Example 38, Step F (41 mg, 0.137 mmol) and dimethyl oxalate (21 mg, 0.17 mmol) were dissolved in DMF (2 mL) under rapid stirring in a 25-mL flask under N2 fitted with a condenser. Potassium tert-butoxide (22 mg, 0.19 mmol) was added, and the mixture was he... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | O.CN(C)C=O | null | null | COC(=O)C(=O)OC.c1ccc2[nH]ccc2c1>O.CN(C)C=O>Cn1ccc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b7c4c1026904250a89432a905e688a7 | COC(=O)C(=O)OC.c1ccc2[nH]ccc2c1>>Cn1ccc2ccccc21 | N1C=CC2=CC=CC=C12.C(C(=O)OC)(=O)OC.CC(C)([O-])C.[K+]>>CN1C=CC2=CC=CC=C12 | COC(=O)C(=O)O[CH3:1].[nH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12 | COC(=O)C(=O)OC.c1ccc2[nH]ccc2c1 | Cn1ccc2ccccc21 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-methylation | 45d087e669e7ced2fcca083b9a7995c8ca53d293f4ea7f1924a30828f449e6a8 | 96828a0648495aff2c1f536e3b5314dc763196d4ff5c85c4b65f7a1f616a38fb | c1ccc2[nH]ccc2c1 | C-O-C(=O)-C(=O)-O-[CH3;D1;+0:1].[c:2]:[c:3]1:[c:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[c:3]:1:[c:2] | 226.3 | [{"value": 96.0, "product": "CN1C=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 226.3, "product": "CN1C=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of the indole product from Example 52 (160 mg, 0.539 mmol) and dimethyl oxalate (70 mg, 0.59 mmol) in DMF (5 mL), potassium tert-butoxide (66 mg, 0.59 mmol) was added in one portion at room temperature under nitrogen. The reaction mixture was warmed to reflux under nitrogen for 30 min and then was cooled ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | O.CN(C)C=O | null | null | COC(=O)C(=O)OC.c1ccc2[nH]ccc2c1>O.CN(C)C=O>Cn1ccc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-81bfe9d130b04b9b973e875432af5744 | C=O.c1ccc2c(c1)CCN2>>CN1CCc2ccccc21 | C(#N)[BH3-].[Na+].N1CCC2=CC=CC=C12.C(C)(=O)O.C=O>>CN1CCC2=CC=CC=C12 | O=[CH2:1].[NH:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]21>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]21 | C=O.c1ccc2c(c1)CCN2 | CN1CCc2ccccc21 | null | null | CO | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | 831ca821d85adad567722fd7fff22eb37d2c95259b7c4e2e50be675464e6c02a | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc2c(c1)CCN2 | O=[CH2;D1;+0:1].[c:2]:[c:3]1:[c:4]-[C:5]-[C:6]-[NH;D2;+0:7]-1>>[CH3;D1;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[c:4]:[c:3]-1:[c:2] | 74 | [{"value": 74.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of the resulting indoline(180 mg, 0.603 mmol) and acetic acid (0.1 mL) in methanol (5 mL), 37% aqueous formaldehyde (0.054 mL, 0.723 mmol) was added dropwise at 0° C. The reaction mixture was stirred at room temperature under nitrogen for 1 h, and then was cooled to 0° C. again. Sodium cyanoborohydride (9... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | Other | CO | null | 1 | C=O.c1ccc2c(c1)CCN2>CO>CN1CCc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ccc6e315b0734760bd2eddf77c0f3649 | COC(=O)C(=O)OC.c1ccc2[nH]ccc2c1>>Cn1ccc2ccccc21 | N1C=CC2=CC=CC=C12.C(C(=O)OC)(=O)OC.CC(C)([O-])C.[K+].Cl>>CN1C=CC2=CC=CC=C12 | COC(=O)C(=O)O[CH3:1].[nH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12 | COC(=O)C(=O)OC.c1ccc2[nH]ccc2c1 | Cn1ccc2ccccc21 | null | null | C(C)OCC.O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-methylation | 45d087e669e7ced2fcca083b9a7995c8ca53d293f4ea7f1924a30828f449e6a8 | 96828a0648495aff2c1f536e3b5314dc763196d4ff5c85c4b65f7a1f616a38fb | c1ccc2[nH]ccc2c1 | C-O-C(=O)-C(=O)-O-[CH3;D1;+0:1].[c:2]:[c:3]1:[c:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[c:3]:1:[c:2] | 95.3 | [{"value": 11.0, "product": "CN1C=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.3, "product": "CN1C=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The indole product from Example 56 (100 mg, 0.36 mmol) and dimethyl oxalate (46 mg, 0.39 mmol) in DMF (3 mL) were treated with potassium t-butoxide (44 mg, 0.39 mmol). The reaction was heated at reflux for 30 min. Reaction was cooled to room temperature and diluted with water (25 mL). Following extractions (3×) with et... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | C(C)OCC.O.CN(C)C=O | null | null | COC(=O)C(=O)OC.c1ccc2[nH]ccc2c1>C(C)OCC.O.CN(C)C=O>Cn1ccc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-767d7cb47d3e4231a793d88d4d6c76ea | COC(=O)C(=O)OC.c1ccc2[nH]ccc2c1>>Cn1ccc2ccccc21 | CC(C)([O-])C.[K+].N1C=CC2=CC=CC=C12.C(C(=O)OC)(=O)OC>>CN1C=CC2=CC=CC=C12 | COC(=O)C(=O)O[CH3:1].[nH:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12>>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12 | COC(=O)C(=O)OC.c1ccc2[nH]ccc2c1 | Cn1ccc2ccccc21 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-methylation | 45d087e669e7ced2fcca083b9a7995c8ca53d293f4ea7f1924a30828f449e6a8 | 96828a0648495aff2c1f536e3b5314dc763196d4ff5c85c4b65f7a1f616a38fb | c1ccc2[nH]ccc2c1 | C-O-C(=O)-C(=O)-O-[CH3;D1;+0:1].[c:2]:[c:3]1:[c:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1>>[CH3;D1;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[c:3]:1:[c:2] | 44 | [{"value": 44.0, "product": "CN1C=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Potassium tert-butoxide was added to a solution of the indole product of Example 61 (354 mg, 1.12 mmol) and dimethyl oxalate (145 mg, 1.23 mmol) in DMF (3 mL) and heated to reflux for 1 h. The mixture was cooled to room temperature and quenched with water (5 mL). After extraction (2×) with CH2Cl2, the organic layer was... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | CN(C)C=O | null | null | COC(=O)C(=O)OC.c1ccc2[nH]ccc2c1>CN(C)C=O>Cn1ccc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7062f8f9039d4fe2bc786da09f888f80 | Cn1ccc2ccccc21>>CN1CCc2ccccc21 | C(#N)[BH3-].[Na+].CN1C=CC2=CC=CC=C12>>CN1CCC2=CC=CC=C12 | [CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]21 | Cn1ccc2ccccc21 | CN1CCc2ccccc21 | null | null | O.C(C)(=O)O | Reduction | OtherReaction | 8369c7c8f75c2f50d07919bea8118ddc2d7f82699b4b8b9637911c242185a734 | 3f9bd1254c561719832bd71149feb4e99c5764db1feb47bf9fbdfb1c414d602b | c1ccc2c(c1)CCN2 | [C;D1;H3:1]-[n;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c:5](:[c:6]):[c:7]:1:[c:8]>>[C;D1;H3:1]-[N;H0;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]-1:[c:8] | 33.6 | [{"value": 15.0, "product": "CN1CCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.6, "product": "CN1CCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Sodium cyanoborohydride (63 mg, 1.004 mmol) was added to an ice-cold solution of the N-methyl indole (110 mg, 0.335 mmol) in glacial acetic acid (6 mL). The reaction mixture was allowed to warm to room temperature, stirred for 2 h, cooled in an ice bath, and diluted with H2O (10 mL). Ice-cold concentrated aq. ammonium ... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2c(c1)CC[NH]2 | c1ccc2c(c1)CC[NH]2 | null | O.C(C)(=O)O | null | 2 | Cn1ccc2ccccc21>O.C(C)(=O)O>CN1CCc2ccccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c9791b0aa5014cb2946e6ff3fc5f2c8a | CC(C(=O)O)(c1ccccc1)c1ccccc1.O=C(Cl)C(=O)Cl>>CC(C(=O)Cl)(c1ccccc1)c1ccccc1 | C(C(=O)Cl)(=O)Cl.C1(=CC=CC=C1)C(C(=O)O)(C)C1=CC=CC=C1>>C1(=CC=CC=C1)C(C(=O)Cl)(C)C1=CC=CC=C1 | O[C:3]([C:2]([CH3:1])([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)=[O:4].O=C(Cl)C(=O)[Cl:5]>>[CH3:1][C:2]([C:3](=[O:4])[Cl:5])([c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | CC(C(=O)O)(c1ccccc1)c1ccccc1.O=C(Cl)C(=O)Cl | CC(C(=O)Cl)(c1ccccc1)c1ccccc1 | null | CN(C=O)C | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccc(Cc2ccccc2)cc1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[C:4](-[C;D1;H3:5])(-[c:6])-[c:7]>>[C;D1;H3:5]-[C:4](-[c:6])(-[c:7])-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:3] | null | [] | 50 | CELSIUS | 0.5 | HOUR | 52.08 g (0.33 mol) of oxalyl chloride are slowly added dropwise at 20° C. to a suspension of 25.0 g (0.11 mol) of 2,2-diphenylpropionic acid, 100 mL of dichloromethane, and 4 drops of dimethylformamide. The mixture is stirred for 1 hour at 20° C. and 0.5 hour at 50° C. The solvent is distilled off and the residue remai... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1ccccc1.c1ccccc1 | HCl | CN(C=O)C.ClCCl | 50 | 0.5 | CC(C(=O)O)(c1ccccc1)c1ccccc1.O=C(Cl)C(=O)Cl>CN(C=O)C.ClCCl>CC(C(=O)Cl)(c1ccccc1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-06c14e7ef5bc4b458558b542fc10a30f | COc1cc(CCNCc2ccccc2C(=O)NCCCCc2ccccc2)ccc1C>>Cc1ccc(CCNCc2ccccc2C(=O)NCCCCc2ccccc2)cc1O | COC=1C=C(C=CC1C)CCNCC1=C(C(=O)NCCCCC2=CC=CC=C2)C=CC=C1.B(Br)(Br)Br.CO>>OC=1C=C(C=CC1C)CCNCC1=C(C(=O)NCCCCC2=CC=CC=C2)C=CC=C1 | C[O:31][c:30]1[c:2]([CH3:1])[cH:3][cH:4][c:5]([CH2:6][CH2:7][NH:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16](=[O:17])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH2:7][NH:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:1... | COc1cc(CCNCc2ccccc2C(=O)NCCCCc2ccccc2)ccc1C | Cc1ccc(CCNCc2ccccc2C(=O)NCCCCc2ccccc2)cc1O | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(NCCCCc1ccccc1)c1ccccc1CNCCc1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 14.5 | [{"value": 14.5, "product": "OC=1C=C(C=CC1C)CCNCC1=C(C(=O)NCCCCC2=CC=CC=C2)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Crude 2-{[2-(3-methoxy-4-methyl-phenyl)-ethylamino]-methyl}-N-(4-phenyl-butyl)-benzamide (derived via Procedure C from 200 mg resin) is dissolved in 3 mL of dichloromethane and treated with 0.5 mL of 1 M of boron tribromide in dichloromethane for 16 h. Methanol (3 mL) is carefully added and the volatiles are removed. T... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | ClCCl | null | null | COc1cc(CCNCc2ccccc2C(=O)NCCCCc2ccccc2)ccc1C>ClCCl>Cc1ccc(CCNCc2ccccc2C(=O)NCCCCc2ccccc2)cc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-66725a1049364b39b741a7bdee9695b0 | NC(=O)CC=Cc1ccccc1>>NCCC=Cc1ccccc1 | C1(=CC=CC=C1)C=CCC(=O)N.[H-].C(C(C)C)[Al+]CC(C)C>>C1(=CC=CC=C1)C=CCCN | O=[C:2]([NH2:1])[CH2:3][CH:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[NH2:1][CH2:2][CH2:3][CH:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | NC(=O)CC=Cc1ccccc1 | NCCC=Cc1ccccc1 | null | null | ClCCl | Reduction | Reduction of primary amides to amines | 71f4ab6e4ff9fd6ad8fb6a6879cdc6c258d35bb85b9b40ad2783b874bf909ba4 | 8776a0c3e2f32dafe87200a597cd55df0b01414bf133bdc9f8f7e1171014bfad | c1ccccc1 | O=[C;H0;D3;+0:1](-[N;D1;H2:2])-[C:3]-[C:4]=[C:5]-[c:6]>>[N;D1;H2:2]-[CH2;D2;+0:1]-[C:3]-[C:4]=[C:5]-[c:6] | 79.3 | [{"value": 79.0, "product": "C1(=CC=CC=C1)C=CCCN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.3, "product": "C1(=CC=CC=C1)C=CCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 4 | DAY | A suspension of 4-phenyl-but-3-enoic acid amide (5.0 g, 31 mmol) in 250 mL dichloromethane was cooled to 0° C. Diisobutylaluminum hydride (1 M in dichloromethane, 250 mL) was added and the resulting homogeneous mixture was allowed to slowly warm to rt. The reaction was stirred for 4 days then quenched by carefully pour... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | null | null | null | c1ccccc1 | Other | ClCCl | 0 | 96 | NC(=O)CC=Cc1ccccc1>ClCCl>NCCC=Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cdf5e48caf8840a28491872246f93c94 | NC(=O)CCOc1ccccc1>>NCCCOc1ccccc1 | O(C1=CC=CC=C1)CCC(=O)N.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>O(C1=CC=CC=C1)CCCN | O=[C:2]([NH2:1])[CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[NH2:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | NC(=O)CCOc1ccccc1 | NCCCOc1ccccc1 | null | null | C(C)OCC | Reduction | Reduction of primary amides to amines | 71f4ab6e4ff9fd6ad8fb6a6879cdc6c258d35bb85b9b40ad2783b874bf909ba4 | 8776a0c3e2f32dafe87200a597cd55df0b01414bf133bdc9f8f7e1171014bfad | c1ccccc1 | O=[C;H0;D3;+0:1](-[N;D1;H2:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[N;D1;H2:2] | 60.6 | [{"value": 60.6, "product": "O(C1=CC=CC=C1)CCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A solution of 3-phenoxy-propionamide (1.0 g, 6.0 mmol) in diethyl ether (30 mL) was cooled to 0 C. Lithium aluminum hydride (0.46 g, 12 mmol) was added in portions to the stirring amide solution. The resulting slurry was allowed to warm to rt and stirred for 20 h. The mixture was cooled to 0° C. and carefully quenched ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | null | null | null | c1ccccc1 | Other | C(C)OCC | null | 20 | NC(=O)CCOc1ccccc1>C(C)OCC>NCCCOc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e96b0f6e3a4f4f18982b5bc493f3a1d2 | O=C1c2ccccc2C(=O)N1CCCBr.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>O=C1c2ccccc2C(=O)N1CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.BrCCCN1C(C=2C(C1=O)=CC=CC2)=O>>[Br-].C1(C=2C(C(N1CCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O)=CC=CC2)=O | [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][CH2:13][CH2:14][Br:34].[P:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)([c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[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][... | O=C1c2ccccc2C(=O)N1CCCBr.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | O=C1c2ccccc2C(=O)N1CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 72a5231b07f184f0ef4a0648badd4176f521b95f1ba3340a0f90d8894af47260 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | O=C1c2ccccc2C(=O)N1CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[C:4].[c:5]:[c:6](-[P;H0;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c:11](:[c:12]):[c:13]):[c:14]>>[Br-;H0;D0:1].[C:4]-[C:3]-[CH2;D2;+0:2]-[P+;H0;D4:7](-[c:6](:[c:5]):[c:14])(-[c:8](:[c:9]):[c:10])-[c:11](:[c:12]):[c:13] | 46.1 | [{"value": 46.1, "product": "[Br-].C1(C=2C(C(N1CCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The 3-phthalimidopropyltriphenylphosphonium bromide was prepared as follows. To a solution of triphenylphosphine (24.5 g, Aldrich, U.S.A.) in toluene (200 mL) was added N-(3-bromopropyl)phthalimide (25 g, Aldrich, U.S.A.). The mixture was heated to reflux overnight. The white solid so formed was isolated by filtration ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccc2c(c1)C[NH]C2.c1ccccc1.c1ccccc1.c1ccccc1 | null | C1(=CC=CC=C1)C | null | null | O=C1c2ccccc2C(=O)N1CCCBr.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C1(=CC=CC=C1)C>O=C1c2ccccc2C(=O)N1CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-789a855a27f04393a01aa7155bdee404 | O=C1c2ccccc2C(=O)N1CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1cccc(Cl)c1>>O=C1c2ccccc2C(=O)N1CC/C=C\c1cccc(Cl)c1 | O.[Br-].C1(C=2C(C(N1CCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=O)=CC=CC2)=O.ClC=1C=C(C=O)C=CC1.CC(C)([O-])C.[K+]>>ClC=1C=C(C=CC1)\C=C/CCN1C(C=2C(C1=O)=CC=CC2)=O | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:14][CH2:13][CH2:12][N:11]2[C:2](=[O:1])[c:3]3[cH:4][cH:5][cH:6][cH:7][c:8]3[C:9]2=[O:10])cc1.O=[CH:15][c:16]1[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13]/[CH:14]=[CH:15]\[c:16]1[cH:17][cH:18][cH:19]... | O=C1c2ccccc2C(=O)N1CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1cccc(Cl)c1 | O=C1c2ccccc2C(=O)N1CC/C=C\c1cccc(Cl)c1 | null | null | O1CCCC1 | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=C1c2ccccc2C(=O)N1CC/C=C\c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[CH2;D2;+0:7]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:5]-[C:6]/[CH;D2;+0:7]=[CH;D2;+0:1]\[c:2](:[c:3]):[c:4] | 64.3 | [{"value": 64.3, "product": "ClC=1C=C(C=CC1)\\C=C/CCN1C(C=2C(C1=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 20 | MINUTE | A mixture of 3-phthalimidopropyltriphenylphosphonium bromide (15.1 g) and 3-chlorobenzaldehyde (4.0 g, Aldrich, U.S.A.) in tetrahydrofuran (150 mL) was cooled to −78° C. in a dry ice/acetone bath. Potassium tert-butoxide (3.2 g) was added and the mixture was stirred for 20 min, then allowed to warm to 0° C. After four ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccc2c(c1)C[NH]C2.c1ccccc1 | HO- | O1CCCC1 | -78 | 0.333333 | O=C1c2ccccc2C(=O)N1CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1cccc(Cl)c1>O1CCCC1>O=C1c2ccccc2C(=O)N1CC/C=C\c1cccc(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a13bbd2a60c451086842b48e8e24bdf | O=C1c2ccccc2C(=O)N1CC/C=C\c1cccc(Cl)c1>>O=C1c2ccccc2C(=O)N1CC/C=C/c1cccc(Cl)c1 | ClC=1C=C(C=CC1)\C=C/CCN1C(C=2C(C1=O)=CC=CC2)=O.II>>ClC=1C=C(C=CC1)/C=C/CCN1C(C=2C(C1=O)=CC=CC2)=O | [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][CH2:13]/[CH:14]=[CH:15]\[c:16]1[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13]/[CH:14]=[CH:15]/[c:16]1[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]1 | O=C1c2ccccc2C(=O)N1CC/C=C\c1cccc(Cl)c1 | O=C1c2ccccc2C(=O)N1CC/C=C/c1cccc(Cl)c1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1c2ccccc2C(=O)N1CC/C=C/c1ccccc1 | null | 26.3 | [{"value": 26.3, "product": "ClC=1C=C(C=CC1)/C=C/CCN1C(C=2C(C1=O)=CC=CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of cis-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide (1.9 g) and iodine (50 mg) in 500 mL toluene was irradiated for 5 days with a 100-watt incandescent light bulb. The solvent was removed in vacuo and the residue was recrystallized from toluene/methanol to give 0.50 g of trans-N-[4-(3-chlorophenyl)-but-3-en... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)C[NH]C2.c1ccccc1 | null | C1(=CC=CC=C1)C | null | null | O=C1c2ccccc2C(=O)N1CC/C=C\c1cccc(Cl)c1>C1(=CC=CC=C1)C>O=C1c2ccccc2C(=O)N1CC/C=C/c1cccc(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3af9858d43a54428aca87fd4a926d00a | O=C1c2ccccc2C(=O)N1CC/C=C/c1cccc(Cl)c1>>NCC/C=C/c1cccc(Cl)c1 | ClC=1C=C(C=CC1)/C=C/CCN1C(C=2C(C1=O)=CC=CC2)=O.CN>>ClC=1C=C(C=CC1)/C=C/CCN | O=C1c2ccccc2C(=O)[N:1]1[CH2:2][CH2:3]/[CH:4]=[CH:5]/[c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[cH:12]1>>[NH2:1][CH2:2][CH2:3]/[CH:4]=[CH:5]/[c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[cH:12]1 | O=C1c2ccccc2C(=O)N1CC/C=C/c1cccc(Cl)c1 | NCC/C=C/c1cccc(Cl)c1 | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | c1ccccc1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3]/[C:4]=[C:5])-C(=O)-c2:c:c:c:c:c:2-1>>[C:5]=[C:4]/[C:3]-[C:2]-[NH2;D1;+0:1] | 68.6 | [{"value": 68.6, "product": "ClC=1C=C(C=CC1)/C=C/CCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of trans-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide (0.50 g) and methylamine (2 M in tetrahydrofuran, 8 mL) in 20 mL ethanol was heated to reflux for 4 h. The solution was cooled to rt and the solvent was removed in vacuo. The resulting residue was dissolved in ethyl acetate and extracted 3 times with 1 M... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccccc1 | HO- | C(C)O | null | null | O=C1c2ccccc2C(=O)N1CC/C=C/c1cccc(Cl)c1>C(C)O>NCC/C=C/c1cccc(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e071135198c14eb6b420a4e8a6fc2321 | O=C1c2ccccc2C(=O)N1CC/C=C\c1cccc(Cl)c1>>NCC/C=C\c1cccc(Cl)c1 | ClC=1C=C(C=CC1)\C=C/CCN1C(C2=CC=CC=C2C1=O)=O.O.NN>>ClC=1C=C(C=CC1)\C=C/CCN | O=C1c2ccccc2C(=O)[N:1]1[CH2:2][CH2:3]/[CH:4]=[CH:5]\[c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[cH:12]1>>[NH2:1][CH2:2][CH2:3]/[CH:4]=[CH:5]\[c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[cH:12]1 | O=C1c2ccccc2C(=O)N1CC/C=C\c1cccc(Cl)c1 | NCC/C=C\c1cccc(Cl)c1 | null | null | C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | c1ccccc1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[C:3]/[C:4]=[C:5])-C(=O)-c2:c:c:c:c:c:2-1>>[C:5]=[C:4]\[C:3]-[C:2]-[NH2;D1;+0:1] | 75.3 | [{"value": 75.3, "product": "ClC=1C=C(C=CC1)\\C=C/CCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of cis-2-[4-(3-chlorophenyl)-but-3-enyl]-isoindole-1,3-dione (5.7 g) and hydrazine hydrate (1.8 mL) in ethanol (180 mL) was heated at reflux for 16 h. The solution was allowed to cool to rt and the volatiles were removed in vacuo. The resulting residue was dissolved in 2 M sodium hydroxide and extracted thre... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccccc1 | HO- | C(C)O | null | null | O=C1c2ccccc2C(=O)N1CC/C=C\c1cccc(Cl)c1>C(C)O>NCC/C=C\c1cccc(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6eda0c359052479e89b251fa31711b9d | NCC/C=C\c1cccc(Cl)c1>>NCCCCc1cccc(Cl)c1 | ClC=1C=C(C=CC1)\C=C/CCN.[H][H]>>ClC=1C=C(C=CC1)CCCCN | [NH2:1][CH2:2][CH2:3]/[CH:4]=[CH:5]\[c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[cH:12]1>>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([Cl:11])[cH:12]1 | NCC/C=C\c1cccc(Cl)c1 | NCCCCc1cccc(Cl)c1 | null | O.[Pt](=O)=O | CO | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccccc1 | [C:1]-[C:2]/[CH;D2;+0:3]=[CH;D2;+0:4]\[c:5](:[c:6]):[c:7]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7] | 74.2 | [{"value": 74.2, "product": "ClC=1C=C(C=CC1)CCCCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of cis-4-(3-chlorophenyl)-but-3-enylamine (1.2 g) in 20 mL methanol was added to platinum(IV) oxide monohydrate (0.12 g). The mixture was stirred under 1 atm of hydrogen for 16 h. The mixture was filtered through celite, and the methanol was removed in vacuo to yield 0.9 g of 4-(3-chlorophenyl)-butylamine.
C... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | O.[Pt](=O)=O.CO | null | null | NCC/C=C\c1cccc(Cl)c1>O.[Pt](=O)=O.CO>NCCCCc1cccc(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-681f0d0de09a4023ad7560518cc95756 | C#CCCC(=O)O.Ic1ccccc1>>O=C(O)CCC#Cc1ccccc1 | C(CCC#C)(=O)O.IC1=CC=CC=C1>>C1(=CC=CC=C1)C#CCCC(=O)O | [O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6]#[CH:7].I[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][C:6]#[C:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | C#CCCC(=O)O.Ic1ccccc1 | O=C(O)CCC#Cc1ccccc1 | null | [Cu]I | C(C)NCC | 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:6]-[C:7]#[CH;D1;+0:8]>>[C:6]-[C:7]#[C;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 28.1 | [{"value": 28.1, "product": "C1(=CC=CC=C1)C#CCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of pent-4-ynoic acid (1.0 g, 10 mmol), iodobenzene (2.3 ml, 20 mmol), copper(I) iodide (75 mg, 0.40 mmol) and dichlorobis(triphenylphosphine)-platinum(II) (140 mg, 0.20 mmol) in 20 mL of diethylamine was stirred at rt for 3 days. The volatile material are evaporated by a rotary evaporator and the resulting r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | [Cu]I.C(C)NCC | null | null | C#CCCC(=O)O.Ic1ccccc1>[Cu]I.C(C)NCC>O=C(O)CCC#Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5939bb060647439fbc9218ef92c27765 | CC(C)(C)O.O=C(O)CCC#Cc1ccccc1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>>CC(C)(C)OC(=O)NCCC#Cc1ccccc1 | C(C)(C)(C)O.C1(=CC=CC=C1)C#CCCC(=O)O.C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-].C(C)N(CC)CC>>C(C)(C)(C)OC(NCCC#CC1=CC=CC=C1)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[OH:5].O[C:6](=[O:7])[CH2:10][CH2:9][C:11]#[C:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[N-]=[N+]=[N:8]P(=O)(c1ccccc1)c1ccccc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:11]#[C:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | CC(C)(C)O.O=C(O)CCC#Cc1ccccc1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1 | CC(C)(C)OC(=O)NCCC#Cc1ccccc1 | null | null | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 3b09548a8be6be1d34bf74d6a7f56636b811d5f7d65884189889317d43936360 | d454d72298ca0c051146c3817785c645d1b1b934cc33fa3fd1ddef4c6f8ea912 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C;H0;D2;+0:5]#[C:6]-[c:7].O=P(-[N;H0;D2;+0:8]=[N+]=[N-])(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.[C;D1;H3:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[OH;D1;+0:13]>>[C;D1;H3:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[O;H0;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-... | null | [] | null | null | null | null | A solution of 5-phenylpent-4-ynoic acid (0.49 g), diphenylphosphoryl azide (0.66 mL) and triethylamine (0.43 mL) was refluxed in 15 mL toluene for 3 h. The reaction was cooled to rt and t-butyl alcohol was added. The reaction was refluxed for 16 h, then the volatile materials were removed via a rotary evaporator. The r... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Azide.Tertiary alcohol.Alkyne | Carbamic ester.Ether.Alkyne.Boc | c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | CC(C)(C)O.O=C(O)CCC#Cc1ccccc1.[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1>C1(=CC=CC=C1)C>CC(C)(C)OC(=O)NCCC#Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-20d2e46c1d1247a2976c93d528f9a3be | CC(C)(C)OC(=O)NCCC#Cc1ccccc1>>NCCC#Cc1ccccc1 | C(C)(C)(C)OC(NCCC#CC1=CC=CC=C1)=O>>C1(=CC=CC=C1)C#CCCN | CC(C)(C)OC(=O)[NH:1][CH2:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[NH2:1][CH2:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | CC(C)(C)OC(=O)NCCC#Cc1ccccc1 | NCCC#Cc1ccccc1 | null | null | FC(C(=O)O)(F)F.ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]-[C:4]#[C:5]>>[C:5]#[C:4]-[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | A solution of (4-phenyl-but-3-ynyl)-carbamic acid tert-butyl ester (98 mg) was stirred for 0.5 h in 1:1 trifluoroacetic acid/dichloromethane (10 ml). The volatile materials were evaporated to give the crude 4-phenyl-but-3-ynylamine, which was used in subsequent transformations without further purification.
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | FC(C(=O)O)(F)F.ClCCl | null | null | CC(C)(C)OC(=O)NCCC#Cc1ccccc1>FC(C(=O)O)(F)F.ClCCl>NCCC#Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1ba07cbda9804effb51403d0992a3d41 | CC(C)(C)OC(=O)NCCC#Cc1ccccc1>>NCC/C=C\c1ccccc1 | C(C)(C)(C)OC(NCCC#CC1=CC=CC=C1)=O>>C1(=CC=CC=C1)\C=C/CCN | CC(C)(C)OC(=O)[NH:1][CH2:2][CH2:3][C:4]#[C:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[NH2:1][CH2:2][CH2:3]/[CH:4]=[CH:5]\[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | CC(C)(C)OC(=O)NCCC#Cc1ccccc1 | NCC/C=C\c1ccccc1 | null | [Pd] | N1=CC=CC=C1 | Reduction | OtherReaction | bdf47f7a69214a8798d851da4e6b88c297b2dfa3785dd56f75ad3d36b70fbc1b | 3e6629bb396188d3c28d59a900376b96b51b1cdb77716e7e78dd9f3f6ebcb98b | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]-[C;H0;D2;+0:4]#[C;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[NH2;D1;+0:1]-[C:2]-[C:3]/[CH;D2;+0:4]=[CH;D2;+0:5]\[c:6](:[c:7]):[c:8] | null | [] | null | null | 1 | HOUR | A suspension of palladium on barium sulfate (15 mg) was stirred for 15 min in 1 mL pyridine. (4-phenyl-but-3-ynyl)-carbamic acid tert-butyl ester (66 mg) was added and the solution was purged with hydrogen then stirred for 1 h under a hydrogen-filled balloon. The solution was diluted with ethyl acetate (10 ml) and wash... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Alkyne.Boc | Primary amine | null | null | c1ccccc1 | HO- | [Pd].N1=CC=CC=C1 | null | 1 | CC(C)(C)OC(=O)NCCC#Cc1ccccc1>[Pd].N1=CC=CC=C1>NCC/C=C\c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e6609cbcbab46a8a867933955519b54 | CC(C)(C)[Si](C)(C)Cl.NC(=O)Cc1ccc(O)c(Cl)c1>>CC(C)(C)[Si](C)(C)Oc1ccc(CC(N)=O)cc1Cl | ClC=1C=C(C=CC1O)CC(=O)N.N1C=NC=C1.[Si](C)(C)(C(C)(C)C)Cl>>[Si](C)(C)(C(C)(C)C)OC1=C(C=C(C=C1)CC(=O)N)Cl | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][C:14]([NH2:15])=[O:16])[cH:17][c:18]1[Cl:19]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][C:14]([NH2:15])=[O:16])[cH:17][c:18]1[Cl:19] | CC(C)(C)[Si](C)(C)Cl.NC(=O)Cc1ccc(O)c(Cl)c1 | CC(C)(C)[Si](C)(C)Oc1ccc(CC(N)=O)cc1Cl | null | null | C(C)(=O)OCC.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;H3:5]-[C:4](-[C;D1;H3:6])(-[C;D1;H3:7])-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 77.4 | [{"value": 77.4, "product": "[Si](C)(C)(C(C)(C)C)OC1=C(C=C(C=C1)CC(=O)N)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-(3-chloro-4-hydroxy-phenyl)-acetamide (100 mg), imidazole (184 mg), and tert-butyldimethylsilyl chloride (163 mg) was stirred for 2 h in 5 mL of dimethylformamide. The solution was diluted with 50 mL of ethyl acetate and washed with 50 mL of sodium carbonate. The ethyl acetate was evaporated to afford 1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccccc1 | HCl | C(C)(=O)OCC.CN(C=O)C | null | null | CC(C)(C)[Si](C)(C)Cl.NC(=O)Cc1ccc(O)c(Cl)c1>C(C)(=O)OCC.CN(C=O)C>CC(C)(C)[Si](C)(C)Oc1ccc(CC(N)=O)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-daa6f6f4c0d14c2293be4cc625e0a459 | CN.COc1ccc(CC(=O)O)cc1>>CNC(=O)Cc1ccc(OC)cc1 | CN.Cl.CN(CCCN=C=NCC)C.COC1=CC=C(C=C1)CC(=O)O.O.ON1NN=CC2=C1C=CC=C2>>COC1=CC=C(C=C1)CC(=O)NC | [CH3:1][NH2:2].O[C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH3:11])[cH:12][cH:13]1>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH3:11])[cH:12][cH:13]1 | CN.COc1ccc(CC(=O)O)cc1 | CNC(=O)Cc1ccc(OC)cc1 | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[C;D1;H3:5]-[NH2;D1;+0:6]>>[C;D1;H3:5]-[NH;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4] | 83.5 | [{"value": 83.5, "product": "COC1=CC=C(C=C1)CC(=O)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Solid 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.60 g) was added to a stirred suspension of (4-methoxyphenyl)acetic acid (0.50 g) and 1-hydroxybenzotriazine hydrate (0.40 g) in 10 mL tetrahydrofuran. The mixture was stirred for 30 min, then methylamine (2.0 M in THF, 6.0 mL) was added. Stirring was ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | O1CCCC1 | null | 0.5 | CN.COc1ccc(CC(=O)O)cc1>O1CCCC1>CNC(=O)Cc1ccc(OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-daef2d8ef2434000bcefaa426439a026 | COc1ccc(CC#N)c(C)c1C>>COc1ccc(CCN)c(C)c1C | COC1=C(C(=C(C=C1)CC#N)C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>COC1=C(C(=C(C=C1)CCN)C)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8]#[N:9])[c:10]([CH3:11])[c:12]1[CH3:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH2:9])[c:10]([CH3:11])[c:12]1[CH3:13] | COc1ccc(CC#N)c(C)c1C | COc1ccc(CCN)c(C)c1C | null | null | C(C)OCC | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[C:3]-[c:4]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[C:3]-[c:4] | 63.5 | [{"value": 63.5, "product": "COC1=C(C(=C(C=C1)CCN)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A solution of (4-methoxy-2,3-dimethylphenyl)acetonitrile (0.20 g) in 15 mL diethyl ether was cooled to 0° C. Lithium aluminum hydride (0.20 g) was added in portions to the stirring nitrile solution. The resulting slurry was allowed to warm to rt and stirred for 20 h. The mixture was cooled to 0° C. and carefully quench... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1 | null | C(C)OCC | null | 20 | COc1ccc(CC#N)c(C)c1C>C(C)OCC>COc1ccc(CCN)c(C)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-66b12eb350804cde8d3d3a98c42becda | CC(=O)Cc1ccc(O)cc1.[NH4+]>>CC(N)Cc1ccc(O)cc1 | Cl.OC1=CC=C(C=C1)CC(C)=O.C(C)(=O)[O-].[NH4+].C(#N)[BH3-].[Na+]>>NC(CC1=CC=C(C=C1)O)C | O=[C:2]([CH3:1])[CH2:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1.[NH4+:3]>>[CH3:1][CH:2]([NH2:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1 | CC(=O)Cc1ccc(O)cc1.[NH4+] | CC(N)Cc1ccc(O)cc1 | null | null | CO | Functional Group Interconversion | OtherReaction | 14af499c4b742b1ab2135a986a4f7f4e6dda0ad50987736be8cf00d531c63192 | 2ef9e3e9915394571ec6196ff6ea06bca9f3dff8c6f6f43c81edc876014a94a5 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[c:4].[NH4+;D0:5]>>[C;D1;H3:2]-[CH;D3;+0:1](-[NH2;D1;+0:5])-[C:3]-[c:4] | 56.2 | [{"value": 56.2, "product": "NC(CC1=CC=C(C=C1)O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | To a solution of 4-hydroxyphenylacetone (0.5 g, Avocado, U.K.) and ammonium acetate (2.54 g, Aldrich, U.S.A.) in 10 mL methanol was added 0.17 g of sodium cyanoborohydride (Aldrich, U.S.A.). After stirring for 72 h at rt, concentrated hydrochloric acid was added dropwise until the solution reached pH 2. The solvent was... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary amine | null | null | c1ccccc1 | HO- | CO | null | 72 | CC(=O)Cc1ccc(O)cc1.[NH4+]>CO>CC(N)Cc1ccc(O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b0f2e62aef4e412897ab38669bbf8635 | CN.COc1ccc2c(c1)CCC(=O)C2>>COc1ccc2c(c1)CCC(CN)C2 | Cl.COC=1C=C2CCC(CC2=CC1)=O.CN.C(#N)[BH3-].[Na+]>>COC=1C=C2CCC(CC2=CC1)CN | [CH3:12][NH2:13].O=[C:11]1[CH2:10][CH2:9][c:7]2[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]2)[CH2:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH:11]([CH2:12][NH2:13])[CH2:14]2 | CN.COc1ccc2c(c1)CCC(=O)C2 | COc1ccc2c(c1)CCC(CN)C2 | null | null | CO.O.C(C)(=O)O | C-C Coupling | OtherReaction | 77e08596fb56b235d4fb595234bafcf60240d809877bc471cb3cdd88ada4a972 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | c1ccc2c(c1)CCCC2 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[c:5].[CH3;D1;+0:6]-[N;D1;H2:7]>>[C:3]-[C:2]-[CH;D3;+0:1](-[CH2;D2;+0:6]-[N;D1;H2:7])-[C:4]-[c:5] | 41.9 | [{"value": 41.9, "product": "COC=1C=C2CCC(CC2=CC1)CN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6-methoxy-3,4-dihydro-1H-naphthalen-2-one (176 mg, Aldrich, U.S.A.), acetic acid (0.57 mL), methylamine (2.0 M in tetrahydrofuran, 5.0 mL), and sodium cyanoborohydride (64 mg) was stirred in 5 mL methanol for 20 h. The solution was acidified to a pH<2 with concentrated hydrochloric acid, diluted with wate... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCC2 | Other | CO.O.C(C)(=O)O | null | null | CN.COc1ccc2c(c1)CCC(=O)C2>CO.O.C(C)(=O)O>COc1ccc2c(c1)CCC(CN)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bbf5b318502845ec93a68e348bf67846 | COC(=O)c1ccc(C=O)cc1.C[N+](=O)[O-]>>COC(=O)c1ccc(C=C[N+](=O)[O-])cc1 | [OH-].[Na+].COC(C1=CC=C(C=C1)C=O)=O.[N+](=O)([O-])C>>COC(C1=CC=C(C=C1)C=C[N+](=O)[O-])=O | O=[CH:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:15][cH:14]1.[CH3:10][N+:11](=[O:12])[O-:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]=[CH:10][N+:11](=[O:12])[O-:13])[cH:14][cH:15]1 | COC(=O)c1ccc(C=O)cc1.C[N+](=O)[O-] | COC(=O)c1ccc(C=C[N+](=O)[O-])cc1 | null | null | CO | C-C Coupling | OtherReaction | 7ede86d40d3d69f429dde089476c8b7ffa9b74bf3050590255e6323d013c2daf | f736727903c0ad5511d468246b8e380897fd19905174c118ffa4ed4d3651f6ea | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[#7;+:6](-[O;-;D1;H0:7])=[O;D1;H0:8]>>[O;-;D1;H0:7]-[#7;+:6](=[O;D1;H0:8])-[CH;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 0.5 | HOUR | Sodium hydroxide (1 N, 2.3 mL) was added dropwise to 4-formyl-benzoic acid methyl ester (0.33 g) and nitromethane (0.11 ml) in 5 mL methanol at 0° C. The solution was acidified after 0.5 h and a precipitate was formed. The precipitate was isolated by filtration to give 228 mg of 4-(2-nitro-vinyl)-benzoic acid methyl es... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Enamine | null | null | c1ccccc1 | HO- | CO | null | 0.5 | COC(=O)c1ccc(C=O)cc1.C[N+](=O)[O-]>CO>COC(=O)c1ccc(C=C[N+](=O)[O-])cc1 |
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