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-d7098213ef994e7f871969c33d7d6733 | CCCCO.Oc1ccc(Br)cc1F>>CCCCOc1ccc(Br)cc1F | N(=NC(=O)OC(C)C)C(=O)OC(C)C.BrC1=CC(=C(C=C1)O)F.C(CCC)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrC1=CC(=C(C=C1)OCCCC)F | O[CH2:4][CH2:3][CH2:2][CH3:1].[OH:5][c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][c:12]1[F:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][c:12]1[F:13] | CCCCO.Oc1ccc(Br)cc1F | CCCCOc1ccc(Br)cc1F | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 95.6 | [{"value": 95.6, "product": "BrC1=CC(=C(C=C1)OCCCC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 0.315 mol of each of 4-bromo-2-fluorophenol (1), 1-butanol and triphenylphosphine were dissolved in 1000 ml of tetrahydrofuran, and 0.315 mol of diisopropyl azodicarboxylate was added dropwise at about 20° C. After the mixture had been stirred overnight, the solvent was removed by distillation in a rotary evaporator, a... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1 | HO- | O1CCCC1 | null | 8 | CCCCO.Oc1ccc(Br)cc1F>O1CCCC1>CCCCOc1ccc(Br)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d72ec14bcd7c4423a145eaa149263f3b | CCCCOc1ccc(-c2ccc(OCC)c(F)c2)cc1F.COC(=O)OC>>O=C1C=CC=C2C1=Cc1ccccc12 | C(OC)(OC)=O.C(CCC)[Li].Cl.C(C)OC1=C(C=C(C=C1)C1=CC(=C(C=C1)OCCCC)F)F>>C1(C=CC=C2C3=CC=CC=C3C=C12)=O | CCCCO[c:12]1[cH:11][cH:10][c:9](-[c:4]2[cH:3][c:8](F)[c:7](OCC)[cH:6][cH:5]2)[cH:14][c:13]1F.CO[C:2](OC)=[O:1]>>[O:1]=[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:7]1=[CH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]12 | CCCCOc1ccc(-c2ccc(OCC)c(F)c2)cc1F.COC(=O)OC | O=C1C=CC=C2C1=Cc1ccccc12 | null | null | O1CCCC1.CCCCCC | C-C Coupling | OtherReaction | e5b15ba84b2ba37cd733f78a51dce674bd6285e4b29a5f812aac175df36f2b0e | 15a1940e22270f845f5603712729e7f951ae2ac4f5fe74812a8b111b8bc3cb17 | O=C1C=CC=C2C1=Cc1ccccc12 | C-C-C-C-O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c;H0;D3;+0:4](-[c;H0;D3;+0:5]2:[cH;D2;+0:6]:[c;H0;D3;+0:7](-F):[c;H0;D3;+0:8](-O-C-C):[cH;D2;+0:9]:[cH;D2;+0:10]:2):[cH;D2;+0:11]:[c;H0;D3;+0:12]:1-F.C-O-[C;H0;D3;+0:13](=[O;D1;H0:14])-O-C>>[O;D1;H0:14]=[C;H0;D3;+0:13]1-[CH;D2;+0:6]=[CH;D2;+0:5]-[CH;D2;+0:10]=[C;H0;D3;+0:9]2-[C;H0... | null | [] | -70 | CELSIUS | 2 | HOUR | 60 mmol of 4-ethoxy-3,3′-difluoro-4′-butoxybiphenyl (5) are introduced into 200 ml of tetrahydrofuran, and the mixture is cooled to −70° C. 120 mmol of a 1.6 M solution of n-butyllithium in hexane are added dropwise, and the mixture is stirred at this temperature for 2 hours. 60 mmol of dimethyl carbonate are subsequen... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carbonic Ester.Ether.Ether | Ketone.Conjugated diene | c1ccccc1.c1ccccc1 | C1=CCC2=Cc3ccccc3C2=C1 | C1=CCC2=Cc3ccccc3C2=C1 | HF | O1CCCC1.CCCCCC | -70 | 2 | CCCCOc1ccc(-c2ccc(OCC)c(F)c2)cc1F.COC(=O)OC>O1CCCC1.CCCCCC>O=C1C=CC=C2C1=Cc1ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eca79e3229d14634afded7b73fa277ff | Brc1ccc(I)cc1.CCOc1ccc(B(O)O)c(F)c1F>>CCOc1ccc(C2(Br)C=CC=CC2)c(F)c1F | BrC1=CC=C(C=C1)I.Cl.[NH3+]N.FC1=C(C=CC(=C1F)OCC)B(O)O.B(=O)[O-].[Na+]>>BrC1(CC=CC=C1)C1=C(C(=C(C=C1)OCC)F)F | I[c:12]1[cH:11][cH:10][c:8]([Br:9])[cH:14][cH:13]1.OB(O)[c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[c:17]([F:18])[c:15]1[F:16]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([C:8]2([Br:9])[CH:10]=[CH:11][CH:12]=[CH:13][CH2:14]2)[c:15]([F:16])[c:17]1[F:18] | Brc1ccc(I)cc1.CCOc1ccc(B(O)O)c(F)c1F | CCOc1ccc(C2(Br)C=CC=CC2)c(F)c1F | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | O.O1CCCC1 | C-C Coupling | OtherReaction | 24147e6c17b57f1fbe9654a7dfabfddb33df908fb9bb12bacd88530f88c84429 | 26a064b072c3f632170c6bc35a0d0971310fe79472b0652670ca7488a1dfe506 | C1=CCC(c2ccccc2)C=C1 | I-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[Br;D1;H0:5]):[cH;D2;+0:6]:[cH;D2;+0:7]:1.O-B(-O)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[F;D1;H0:12]):[c:13]>>[Br;D1;H0:5]-[C;H0;D4;+0:4]1(-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11](-[F;D1;H0:12]):[c:13])-[CH2;D2;+0:6]-[CH;D2;+0:7]=[CH;D2;+0:1]-[CH;D2;+0:2]=[CH;D2;... | null | [] | 20 | CELSIUS | 5 | MINUTE | 0.450 mol of sodium metaborate are introduced into 240 ml of water. 0.012 mol of bis(triphenylphosphine)palladium(II) chloride, 0.6 mol of 4-bromo-1-iodobenzene (11) and 0.012 mol of hydrazinium hydrochloride are added, and the mixture is stirred at about 20° C. for 5 minutes. 0.6 mol of 2,3-difluoro-4-ethoxyphenylboro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Boronic acid | Tertiary halide.Conjugated diene | c1ccccc1.c1ccccc1 | c1ccccc1.C1=CCCC=C1 | c1ccccc1.C1=CCCC=C1 | I-.B | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.O.O1CCCC1 | 20 | 0.083333 | Brc1ccc(I)cc1.CCOc1ccc(B(O)O)c(F)c1F>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl.O.O1CCCC1>CCOc1ccc(C2(Br)C=CC=CC2)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0b9a94fdaf9742109279595824d5e13c | CCOc1ccc(-c2ccccc2B(O)O)c(F)c1F.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>c1ccc(-c2ccccc2-c2ccccc2)cc1 | FC1=C(C=CC(=C1F)OCC)C=1C(=CC=CC1)B(O)O.BrC1=CC(=C(C=C1)I)F.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C([O-])([O-])=O.[Na+].[Na+]>>C1(=CC=CC=C1)C=1C(=CC=CC1)C1=CC=CC=C1 | CCOc1ccc(-[c:10]2[c:5](B(O)O)[cH:6][cH:7][cH:8][cH:9]2)c(F)c1F.c1ccc(P([c:4]2[cH:3][cH:2][cH:1][cH:18][cH:17]2)[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)cc1>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1 | CCOc1ccc(-c2ccccc2B(O)O)c(F)c1F.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | c1ccc(-c2ccccc2-c2ccccc2)cc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | O.C(C)(C)O | C-C Coupling | OtherReaction | f8945fe9c079a69871e2c5a84e61f8ea58863b43334dfad26abc5ead49040606 | 77a9334ff309e7ea03168ea8c67a45d16cf2750ac0108bbb5ee5802c9501105d | c1ccc(-c2ccccc2-c2ccccc2)cc1 | C-C-O-c1:c:c:c(-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:2-B(-O)-O):c(-F):c:1-F.[c:7]:[c:8]:[c;H0;D3;+0:9](-P(-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14])-c1:c:c:c:c:c:1):[c:15]:[c:16]>>[c:7]:[c:8]:[c;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:1-[c;H0;D3;+0:10](:[c:11]:[c:12]):... | null | [] | null | null | null | null | 0.047 mol of 2′,3′-difluoro-4′-ethoxybiphenylboronic acid (14), 0.05 mol of 1-bromo-3-fluoro-4-iodobenzene (15), 1 mmol of palladium acetate, 2 mmol of triphenylphosphine, 25 ml of saturated sodium carbonate solution, 20 ml of water and 100 ml of isopropanol are initially introduced and refluxed overnight. Conventional... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Boronic acid | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HF.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.C(C)(C)O | null | null | CCOc1ccc(-c2ccccc2B(O)O)c(F)c1F.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].O.C(C)(C)O>c1ccc(-c2ccccc2-c2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d9f85d7ffa8444e78678cc9498e7bd8a | ClN1C=Cc2ccccc2C1.OB(O)c1ccccc1>>c1ccc(-c2nccc3ccccc23)cc1 | ClN1CC2=CC=CC=C2C=C1.C1(=CC=CC=C1)B(O)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+]>>C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12 | Cl[N:6]1[CH2:5][c:14]2[c:9]([cH:10][cH:11][cH:12][cH:13]2)[CH:8]=[CH:7]1.OB(O)[c:4]1[cH:3][cH:2][cH:1][cH:16][cH:15]1>>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[n:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[cH:15][cH:16]1 | ClN1C=Cc2ccccc2C1.OB(O)c1ccccc1 | c1ccc(-c2nccc3ccccc23)cc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C(OC)COC | C-C Coupling | OtherReaction | a68c8cee464e8b848d31a64c983925882ceef8ec8515b34c884232707601f1dd | 0bd0588c783a70e7d53efd630a4969b18d3b156f02f4c1f8e8551696045d6d66 | c1ccc(-c2nccc3ccccc23)cc1 | Cl-[N;H0;D3;+0:1]1-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5](:[c:6])-[CH;D2;+0:7]=[CH;D2;+0:8]-1.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[c:6]:[c:5]1:[cH;D2;+0:7]:[cH;D2;+0:8]:[n;H0;D2;+0:1]:[c;H0;D3;+0:2](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[c:3]:1:[c:4] | 96.9 | [{"value": 96.9, "product": "C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.9, "product": "C1(=CC=CC=C1)C1=NC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Chloro-isoquinoline (28.8 g, 0.176 mol), phenylboronic acid (25.7 g 0.211 mol), triphenylphosphine (4.6 g 17.6 mmol), palladium acetate (0.99 g 4.4 mmol) and 2M solution of potassium carbonate (65.7 g 0.475 mol) were added to 270 ml of dimethoxyethane. This mixture was stirred at reflux for 17 hrs. The mixture was th... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Boronic acid | null | C1=Cc2ccccc2C[NH]1.c1ccccc1 | c1ccccc1.c1ccc2cnccc2c1 | c1ccccc1.c1ccc2cnccc2c1 | HCl.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(OC)COC | null | null | ClN1C=Cc2ccccc2C1.OB(O)c1ccccc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(OC)COC>c1ccc(-c2nccc3ccccc23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f9a41ba85d96457aa547e1997e89c67d | C=C(C)C(=O)O.CC(C)(C)OC(=O)CBr>>C=C(C)C(=O)OCC(=O)OC(C)(C)C | N#N.C(C(=C)C)(=O)O.BrCC(=O)OC(C)(C)C.C1CCC2=NCCCN2CC1>>C(C)(C)(C)OC(COC(C(=C)C)=O)=O | [CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[OH:6].Br[CH2:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14]>>[CH2:1]=[C:2]([CH3:3])[C:4](=[O:5])[O:6][CH2:7][C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14] | C=C(C)C(=O)O.CC(C)(C)OC(=O)CBr | C=C(C)C(=O)OCC(=O)OC(C)(C)C | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | d0f2e7dd04291aff91491624f6ba09bd6ae2852adc109edeabfddd534d9ccfd8 | ebb133741743004d799d6738504ddfd5b4a53248a4f85602c0fff1c33566ad58 | null | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[C;D1;H2:9]=[C:10](-[C;D1;H3:11])-[C:12](=[O;D1;H0:13])-[OH;D1;+0:14]>>[C;D1;H2:9]=[C:10](-[C;D1;H3:11])-[C:12](=[O;D1;H0:13])-[O;H0;D2;+0:14]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8] | null | [] | null | null | 1 | HOUR | Methacrylic acid (8.06 g, 0.10 mole), t-butyl bromoacetate (19.50 g, 0.10 mole) and 1,8-diazabicyclo[5.4.0]undoc-7-ene, DBU, (15.20 g, 0.10 mole) and 150 ml toluene were combined in a 500 ml 3-neck flask equipped with condenser, nitrogen inlet, thermometer and magnetic stirrer bar. The reaction mixture was stirred at r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid | Ester.Ester | null | null | null | HBr | C1(=CC=CC=C1)C | null | 1 | C=C(C)C(=O)O.CC(C)(C)OC(=O)CBr>C1(=CC=CC=C1)C>C=C(C)C(=O)OCC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8ffe0e1859a94fc688a47d34ee7139b2 | CC(=O)Cl.CCN(CCO)c1ccccc1>>CCN(CCOC(C)=O)c1ccccc1 | O.C(C)N(C1=CC=CC=C1)CCO.C(C)N(CC)CC.C(C)(=O)Cl>>C(C)(=O)OCCN(C1=CC=CC=C1)CC | Cl[C:7]([CH3:8])=[O:9].[CH3:1][CH2:2][N:3]([CH2:4][CH2:5][OH:6])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH2:5][O:6][C:7]([CH3:8])=[O:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | CC(=O)Cl.CCN(CCO)c1ccccc1 | CCN(CCOC(C)=O)c1ccccc1 | null | null | CC(=O)C | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | c1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | 99.9 | [{"value": 99.9, "product": "C(C)(=O)OCCN(C1=CC=CC=C1)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 51.8 g of 2-(N-ethylanilino)ethanol and 31.7 g of triethylamine were dissolved in 320 ml of acetone, and to this solution 24.9 g of acetyl chloride was slowly added dropwise while stirring under ice cooling. This mixture was stirred for 3 hours at room temperature, and the reaction solution was poured into 500 ml of wa... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | c1ccccc1 | HCl | CC(=O)C | null | null | CC(=O)Cl.CCN(CCO)c1ccccc1>CC(=O)C>CCN(CCOC(C)=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-34275707ff204c1a9665c1e2feedc6dc | CCN(CCOC(C)=O)c1ccc(C=O)cc1.O=C1CCCCC1.[OH-]>>CCN(CCO)c1ccc(C=C2CCCC(=Cc3ccc(N(CC)CCO)cc3)C2=O)cc1 | C(C)(=O)OCCN(C1=CC=C(C=C1)C=O)CC.C1(CCCCC1)=O.[OH-].[Na+]>>C(C)N(C1=CC=C(C=C1)C=C1C(C(CCC1)=CC1=CC=C(C=C1)N(CCO)CC)=O)CCO | O=[C:2]([CH3:1])[O:6][CH2:5][CH2:4][N:3]([c:7]1[cH:8][cH:9][c:10]([CH:11]=O)[cH:32][cH:33]1)[CH2:23][CH3:24].[CH2:12]1[CH2:13][CH2:19][CH2:20][C:21](=[O:31])[CH2:30]1.[OH-:27]>>[CH3:1][CH2:2][N:3]([CH2:4][CH2:5][OH:6])[c:7]1[cH:8][cH:9][c:10]([CH:11]=[C:12]2[CH2:13][CH2:14][CH2:15][C:16](=[CH:17][c:18]3[cH:19][cH:20][c... | CCN(CCOC(C)=O)c1ccc(C=O)cc1.O=C1CCCCC1.[OH-] | CCN(CCO)c1ccc(C=C2CCCC(=Cc3ccc(N(CC)CCO)cc3)C2=O)cc1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | b192ce4c3d5c99a43991cddb805f904196d7633978bb5776af97c92a55a07b63 | 78009ba978d0ceae9d1dc423bbe7021c0591263ff5884ce533831826b7b1437a | O=C1C(=Cc2ccccc2)CCCC1=Cc1ccccc1 | O=[CH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[N;H0;D3;+0:6](-[C:7]-[C:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:10](=O)-[C;D1;H3:11])-[CH2;D2;+0:12]-[C;D1;H3:13]):[c:14]:[c:15]:1.[O;H0;D1;+0:16]=[C;H0;D3;+0:17]1-[CH2;D2;+0:18]-[CH2;D2;+0:19]-[CH2;D2;+0:20]-[CH2;D2;+0:21]-[CH2;D2;+0:22]-1.[OH-;D0:23]>>[C;D1;H3:11]-[CH2;D2;+0:10]-[N;H0;... | 185.2 | [{"value": 185.2, "product": "C(C)N(C1=CC=C(C=C1)C=C1C(C(CCC1)=CC1=CC=C(C=C1)N(CCO)CC)=O)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | 23.5 g of 2-(ethyl(4-formylphenyl)amino)ethyl acetate, 4.91 g of cyclohexanone and 150 ml of ethanol were mixed and to this was added an aqueous solution (25 ml) of 2.2 g of sodium hydroxide while stirring at 50° C. This mixture was further stirred for 5 hours. After cooling to room temperature, a precipitate was filtr... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone.Ester.Tertiary amine | Ketone.Primary alcohol.Primary alcohol.Tertiary amine.Tertiary amine | C1CCCCC1 | C1CCCCC1.c1ccccc1 | c1ccccc1.C1CCCCC1.c1ccccc1 | null | C(C)O | 50 | null | CCN(CCOC(C)=O)c1ccc(C=O)cc1.O=C1CCCCC1.[OH-]>C(C)O>CCN(CCO)c1ccc(C=C2CCCC(=Cc3ccc(N(CC)CCO)cc3)C2=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-276671e04862474aa4387e04ebc7e0b5 | Nc1ccc2c(=O)[nH][nH]c(=O)c2c1>>Nc1cccc2c(=O)[nH][nH]c(=O)c12 | CN(C)C=O.C1=CC2=C(C=C1N)C(=O)NNC2=O>>C1=CC2=C(C(=C1)N)C(=O)NNC2=O | [NH2:1][c:2]1[cH:3][c:13]2[c:6]([cH:5][cH:4]1)[c:7](=[O:8])[nH:9][nH:10][c:11]2=[O:12]>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7](=[O:8])[nH:9][nH:10][c:11](=[O:12])[c:13]12 | Nc1ccc2c(=O)[nH][nH]c(=O)c2c1 | Nc1cccc2c(=O)[nH][nH]c(=O)c12 | null | null | null | Miscellaneous | OtherReaction | 2958a78cdf1571124dfc971b67140b8b51f8a1fd9b61f3100d91245dc9f6104a | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=c1[nH][nH]c(=O)c2ccccc12 | [N;D1;H2:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c;H0;D3;+0:4]2:[c:5](=[O;D1;H0:6]):[#7;a:7]:[#7;a:8]:[c:9](=[O;D1;H0:10]):[c:11]:2:[c:12]:[cH;D2;+0:13]:1>>[N;D1;H2:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:13]:[c:12]:[c:11]2:[c:9](=[O;D1;H0:10]):[#7;a:8]:[#7;a:7]:[c:5](=[O;D1;H0:6]):[c;H0;D3;+0:4]:2:1 | null | [] | null | null | null | null | About 1 mg of Vitamin D binding protein, DBP, is buffer exchanged three times with 100 mM PBS at pH 8.2. The final volume was 200 uL. Succinyl-amino-buty-ethyl-isoluminol NHS ester (4.6 mg) is dissolved in DMF. The isoluminol (17 uL) is added to the DBP and the mixture is maintained at room temperature for about 1 hour... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=c2ccccc2=CNN1 | C1=c2ccccc2=CNN1 | C1=c2ccccc2=CNN1 | null | null | null | null | Nc1ccc2c(=O)[nH][nH]c(=O)c2c1>>Nc1cccc2c(=O)[nH][nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-34edcaa7e3ba4173928e329654c5e7d9 | O=C(CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21)NCCCCCC(=O)ON1C(=O)CC(S(=O)(=O)[O-])C1=O>>O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21 | C([O-])(O)=O.C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)NCCCCCC(=O)ON3C(=O)CC(C3=O)S(=O)(=O)[O-])NC(=O)N2.[Na+]>>OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12 | O=C(CCCCCN[C:2](=[O:1])[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:8]1[S:9][CH2:10][C@@H:11]2[NH:12][C:13](=[O:14])[NH:15][C@H:16]12)ON1C(=O)CC(S(=O)(=O)[O-])C1=O>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:8]1[S:9][CH2:10][C@@H:11]2[NH:12][C:13](=[O:14])[NH:15][C@H:16]12 | O=C(CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21)NCCCCCC(=O)ON1C(=O)CC(S(=O)(=O)[O-])C1=O | O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21 | null | null | O | Miscellaneous | Oxidation of amide to carboxylic acid | 62e278fda2673d37ab1043207b8d7b8eea62f64281613e4dde1953cdd8fd288d | a579c296c52361ddbd71a28ea32c062e3bd81eb84137ee3f44c507ab24af7ec9 | O=C1N[C@H]2CSC[C@H]2N1 | O=C(-C-C-C-C-C-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4])-O-N1-C(=O)-C-C(-S(=O)(=O)-[O-])-C-1=O>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;D1;H1:5] | null | [] | null | null | 4 | MINUTE | About 2.0 mg of DBP is buffer exchanged with 20 mM bicarbonate at pH 9.6 three times to give a final volume of 1.0 mL. Two aliquots of sulfo-NHS-LC-biotin (Pierce) are dissolved in water to give a 1 mg/mL solution just prior to addition. The first aliquot (10 uL) is added and the reaction is maintained at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Tertiary amide.Tertiary amide.Sulfonic acid | Carboxylic acid | C1CCNC1 | null | C1N[C@H]2CSC[C@H]2N1 | HO- | O | null | 0.066667 | O=C(CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21)NCCCCCC(=O)ON1C(=O)CC(S(=O)(=O)[O-])C1=O>O>O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a58080e00e764f4f9ecc3343f178b2be | O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO>>OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O | CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C=3C=CC=CC3)N)C(=O)O)C.CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C=3C=CC=CC3)N)C(=O)O)C.CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC.O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO.O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO.C[C@@H]1CC(=O)[C@]2([C@@H](O1)O[C@@H]3[C... | [OH:1][CH2:2][C@@H:3]([OH:4])[C@@H:11]([C@@H:9]([C@H:7]([CH:5]=[O:6])[OH:8])[OH:10])[OH:12]>>[OH:1][CH2:2][C@H:3]1[O:4][CH:5]([OH:6])[C@H:7]([OH:8])[C@@H:9]([OH:10])[C@H:11]1[OH:12] | O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO | OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O | null | null | OCC(O)CO | Heteroatom Alkylation and Arylation | OtherReaction | dd33a789286640dba431fbee315fe5133b49e36a8cf19e8a8c4cb319208abf4a | 125aab717b417847558f582772c0fc28476c151b88628553e6b2e16bfc3d5da7 | C1CCOCC1 | [C:1]-[C:2](-[OH;D1;+0:3])-[C:4]-[C:5]-[C:6](-[O;D1;H1:7])-[CH;D2;+0:8]=[O;H0;D1;+0:9]>>[C:1]-[C:2]1-[C:4]-[C:5]-[C:6](-[O;D1;H1:7])-[CH;D3;+0:8](-[OH;D1;+0:9])-[O;H0;D2;+0:3]-1 | null | [] | null | null | 8 | HOUR | Eight co-integrants each from the crosses summarized in Table 2 were streaked for single colonies (from cultures cryo-preserved in 10% glycerol; described in Section 6.4)) on Luria broth plates with ampicillin (100 μg/ml), spectinomycin (50 μg/ml) and gentamycin (10 μg/ml). Single colonies were inoculated into Luria br... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary alcohol | Ether.Secondary alcohol | null | C1CCOCC1 | C1CCOCC1 | null | OCC(O)CO | null | 8 | O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO>OCC(O)CO>OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d94a106a50a34f4c8ff61ec4d39c08b9 | CCCC(=O)Oc1cc2oc(=O)c(C(=O)NCC(=O)OCc3ccccc3)cc2cc1Cl>>CCCC(=O)Oc1cc2oc(=O)c(C(=O)NCC(=O)O)cc2cc1Cl | [H][H].C(CCC)(=O)OC1=C(C=C2C=C(C(OC2=C1)=O)C(=O)NCC(=O)OCC1=CC=CC=C1)Cl.C(C)(=O)O.[H][H]>>C(CCC)(=O)OC1=C(C=C2C=C(C(OC2=C1)=O)C(=O)NCC(=O)O)Cl | c1ccc(C[O:20][C:18]([CH2:17][NH:16][C:14]([c:13]2[c:11](=[O:12])[o:10][c:9]3[cH:8][c:7]([O:6][C:4]([CH2:3][CH2:2][CH3:1])=[O:5])[c:24]([Cl:25])[cH:23][c:22]3[cH:21]2)=[O:15])=[O:19])cc1>>[CH3:1][CH2:2][CH2:3][C:4](=[O:5])[O:6][c:7]1[cH:8][c:9]2[o:10][c:11](=[O:12])[c:13]([C:14](=[O:15])[NH:16][CH2:17][C:18](=[O:19])[OH... | CCCC(=O)Oc1cc2oc(=O)c(C(=O)NCC(=O)OCc3ccccc3)cc2cc1Cl | CCCC(=O)Oc1cc2oc(=O)c(C(=O)NCC(=O)O)cc2cc1Cl | null | [Pd] | O1CCOCC1 | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc2ccccc2o1 | [C:1]-[C:2](=[O;D1;H0:3])-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1>>[C:1]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:4] | null | [] | null | null | null | null | 7-Butyryloxy-3-carboxymethylaminocarbonyl-6-chlorocoumarin was prepared as follows. 920 mg (2 mMol) 7-butyryloxy-3-benzyloxycarbonylmethylaminocarbonyl-6-chlorocoumarin were dissolved in 50 ml dioxane. 100 mg palladium on carbon (10%) and 100 microliters acetic acid were added to the solution and the suspension stirred... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccc2occcc2c1 | Other | [Pd].O1CCOCC1 | null | null | CCCC(=O)Oc1cc2oc(=O)c(C(=O)NCC(=O)OCc3ccccc3)cc2cc1Cl>[Pd].O1CCOCC1>CCCC(=O)Oc1cc2oc(=O)c(C(=O)NCC(=O)O)cc2cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd15db25f90240b191400b49b2751000 | COc1ccc(CSCCCCCCCCCCCCBr)cc1.O=C(O)CCCCCCCCCCCS>>COc1ccc(CSCCCCCCCCCCCCSCCCCCCCCCCCC(=O)O)cc1 | COC1=CC=C(CSCCCCCCCCCCCCBr)C=C1.SCCCCCCCCCCCC(=O)O.C[O-].CO.CO>>COC1=CC=C(CSCCCCCCCCCCCCSCCCCCCCCCCCC(=O)O)C=C1 | Br[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][S:8][CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:37][cH:36]1.[SH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33](=[O:34])[OH:35]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH... | COc1ccc(CSCCCCCCCCCCCCBr)cc1.O=C(O)CCCCCCCCCCCS | COc1ccc(CSCCCCCCCCCCCCSCCCCCCCCCCCC(=O)O)cc1 | null | null | CCOC(=O)C.C(C)(=O)O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 77cd742b5ba20df0e225494f6e5f3d958ee82ce9a1b16fd99a2d9f8350b4fdc8 | b05f7dda7dad719ae1868a84c33eeaf5bf649036fc64173cf4774a5eb4d70181 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[SH;D1;+0:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:6]-[C:5]-[C:4] | 49 | [{"value": 49.0, "product": "COC1=CC=C(CSCCCCCCCCCCCCSCCCCCCCCCCCC(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.7, "product": "COC1=CC=C(CSCCCCCCCCCCCCSCCCCCCCCCCCC(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | Na (116 mg, 5 mmol) was dissolved it dry MeOH. 12-mercapto-1-dodecanoic acid (340 mg, 1.46 mmol)—synthesized according to JACS 115, 3458–3474, 1993—was added to the methoxide solution. After stirring with some heating for 5 min, (2) (497 mg, 1.24 mmol) was added to the reaction. The reaction became very viscous and an ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aliphatic thiol | Monosulfide | null | null | c1ccccc1 | HBr | CCOC(=O)C.C(C)(=O)O | null | 0.083333 | COc1ccc(CSCCCCCCCCCCCCBr)cc1.O=C(O)CCCCCCCCCCCS>CCOC(=O)C.C(C)(=O)O>COc1ccc(CSCCCCCCCCCCCCSCCCCCCCCCCCC(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2ab4c69ffe444c58afdc1046b831250f | C[N+](C)(C)CC(O)CCl.[Cl-]>>C[N+](C)(C)CCCO.[Cl-] | OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.[Cl-].ClCC(C[N+](C)(C)C)O.[OH-].[Na+].OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>[Cl-].OCCC[N+](C)(C)C.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO | Cl[CH2:7][CH:6]([CH2:5][N+:2]([CH3:1])([CH3:3])[CH3:4])[OH:8].[Cl-:21]>>[CH3:1][N+:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][CH2:7][OH:8].[Cl-:21] | C[N+](C)(C)CC(O)CCl.[Cl-] | C[N+](C)(C)CCCO.[Cl-] | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | fc951f63d0c998ede5197f634065a1790ab013a6437aa03e3288e50bfe0f5e60 | 83c338d888ff405ee347e0cb1ab22bb61cb7dfdd74f9374da3ce0a74792dced1 | null | Cl-[CH2;D2;+0:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[C:4]-[#7;+:5]>>[#7;+:5]-[C:4]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[OH;D1;+0:3] | null | [] | null | null | null | null | Herein is provided a synthesis procedure for the chloride salt of hydroxypropyltrimonium sorbitol (also referred to as ‘Sorbitol Monoquat’). A round bottom 250 ml flask was fitted with a mechanical stirrer. Into the flask was charged a mixture of sorbitol (10 g, 55.0 mmol) and 3-chloro-2-hydroxypropyl trimethylammonium... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary alcohol | Primary alcohol | null | null | null | Other | null | null | null | C[N+](C)(C)CC(O)CCl.[Cl-]>>C[N+](C)(C)CCCO.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b7b3ed40ed644461b6f858f1a00c0109 | C(=NC1CCCCC1)=NC1CCCCC1.CCNCC.COC(=O)C(N)Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1.Oc1cccc2[nH]nnc12>>COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C(N)Cc1c[nH]cn1.Cl | C(C)NCC.C1(CCCCC1)N=C=NC1CCCCC1.Cl.NC(CC1=CC=C(OC2=CC=C(C=C3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC.OC1=CC=CC=2NN=NC21>>Cl.Cl.NC(C(=O)NC(CC1=CC=C(OC2=CC=C(CC3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC)CC=1N=CNC1 | C1CCC(N=[C:31]=[N:32]C2CCCCC2)CC1.C[CH2:35][NH:36][CH2:37]C.[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][c:12]2[cH:13][cH:14][c:15]([CH:16]=[C:17]3[S:18][C:19](=[O:20])[NH:21][C:22]3=[O:23])[cH:24][cH:25]2)[cH:26][cH:27]1)[NH2:28].c1c[c:29]([OH:30])[c:34]2[c:33](c1)[nH]n[n:38]2>>[CH3:1][O:2][C... | C(=NC1CCCCC1)=NC1CCCCC1.CCNCC.COC(=O)C(N)Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1.Oc1cccc2[nH]nnc12 | COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C(N)Cc1c[nH]cn1.Cl | null | null | CN(C=O)C | Acylation | OtherReaction | 473e366d878e6f02fc99238eb9646fb1dcba650de30ad2973ed38753b5eb9ca0 | 3ca32cd4aad0c21eca7cfaa8c2b6f616c4b02f5e2f2fcbf465c0d443b194706c | O=C(CCc1c[nH]cn1)NCCc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1 | C-[CH2;D2;+0:1]-[NH;D2;+0:2]-[CH2;D2;+0:3]-C.C1-C-C-C(-N=[C;H0;D2;+0:4]=[N;H0;D2;+0:5]-C2-C-C-C-C-C-2)-C-C-1.[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12].[O;D1;H0:13]=[C:14]1-[#16:15]-[C;H0;D3;+0:16](=[CH;D2;+0:17]-[c:18](:[c:19]):[c:20])-[C:21](=[O;D1;H0:22])-[#7:23]-1.[OH;D1;+0:24]-[c;H0;D3;+... | 163.8 | [{"value": 79.0, "product": "Cl.Cl.NC(C(=O)NC(CC1=CC=C(OC2=CC=C(CC3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC)CC=1N=CNC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 163.8, "product": "Cl.Cl.NC(C(=O)NC(CC1=CC=C(OC2=CC=C(CC3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC)CC=1N=CNC1", "details": "CALCULATEDPERCENTYIELD", "is_desire... | null | null | 24 | HOUR | Diethylamine (1.04 ml, 6.0 mmol) and N,N′-dicyclohexylcarbodiimide (0.64 g, 3.13 mmol) were added to the stirred suspension of 5-[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione hydrochloride (1.3 g, 3.0 mmol), 2-N-t-butoxycarbonylamino-4-imidazole propionic acid (0.8 g, 3.13 mmol) and hy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine.Secondary amine.Monosulfide | Secondary amide.Primary amine.Monosulfide | C1CCCCC1.C1CCCCC1.C1CSCN1.c1ccc2[nH]nnc2c1 | C1CSCN1.c1c[nH]cn1 | c1ccccc1.c1ccccc1.C1CSCN1.c1c[nH]cn1 | Other | CN(C=O)C | null | 24 | C(=NC1CCCCC1)=NC1CCCCC1.CCNCC.COC(=O)C(N)Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1.Oc1cccc2[nH]nnc12>CN(C=O)C>COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C(N)Cc1c[nH]cn1.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-26ebee2f65de419a88e12f4b2597d1eb | C(=NC1CCCCC1)=NC1CCCCC1.CN(C)C=O.COC(=O)C(N)Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1>>COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C(N)Cc1c[nH]cn1.Cl | O.Cl.NC(CC1=CC=C(OC2=CC=C(C=C3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC.CN(C=O)C.C1(CCCCC1)N=C=NC1CCCCC1>>Cl.Cl.NC(C(=O)NC(CC1=CC=C(OC2=CC=C(CC3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC)CC=1N=CNC1 | C1CCC([N:32]=[C:31]=[N:38][CH:34]2[CH2:33]CCC[CH2:35]2)CC1.C[N:36]([CH:29]=[O:30])[CH3:37].[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][c:12]2[cH:13][cH:14][c:15]([CH:16]=[C:17]3[S:18][C:19](=[O:20])[NH:21][C:22]3=[O:23])[cH:24][cH:25]2)[cH:26][cH:27]1)[NH2:28]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]... | C(=NC1CCCCC1)=NC1CCCCC1.CN(C)C=O.COC(=O)C(N)Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1 | COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C(N)Cc1c[nH]cn1.Cl | null | null | null | Acylation | OtherReaction | 20b01e7dfa9851a73e9e8c5479f0a8661b682b55c889bfc071b442603174a3e5 | 1a4d3415d2184a745da04c57f5f66f1606ca66eda2f7c1d8c081f34200c7f7da | O=C(CCc1c[nH]cn1)NCCc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1 | C-[N;H0;D3;+0:1](-[CH3;D1;+0:2])-[CH;D2;+0:3]=[O;D1;H0:4].C1-C-C-C(-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[CH;D3;+0:8]2-[CH2;D2;+0:9]-C-C-C-[CH2;D2;+0:10]-2)-C-C-1.[C:11]-[C:12](-[NH2;D1;+0:13])-[C:14](=[O;D1;H0:15])-[#8:16]-[C;D1;H3:17].[O;D1;H0:18]=[C:19]1-[#16:20]-[C;H0;D3;+0:21](=[CH;D2;+0:22]-[c:23](:[c:24]... | 51 | [{"value": 51.0, "product": "Cl.Cl.NC(C(=O)NC(CC1=CC=C(OC2=CC=C(CC3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC)CC=1N=CNC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | A solution of 5-[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione hydrochloride (6 g, 13.7 mmol) and 2-N-t-butoxy-carbonylamino-4-imidazole propionic acid (5.2 g, 20.3 mmol) in N,N-dimethylformamide (200 ml) was stirred for 1 h at −10° C. N,N′-Dicyclohexylcarbodiimide (4.5 g, 21.8 mmol) wa... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary amine.Monosulfide | Secondary amide.Primary amine.Monosulfide | C1CCCCC1.C1CCCCC1.C1CSCN1 | C1CSCN1.c1c[nH]cn1 | c1ccccc1.c1ccccc1.C1CSCN1.c1c[nH]cn1 | Other | null | null | 12 | C(=NC1CCCCC1)=NC1CCCCC1.CN(C)C=O.COC(=O)C(N)Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1>>COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C(N)Cc1c[nH]cn1.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-63d709e139114d61af6aab85262e9c8f | CC(C)(C)OC(=O)N1CCCC1C(=O)O.COC(=O)C(N)Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1>>COC(=O)C(Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1)NC(=O)C1CCCN1C(=O)OC(C)(C)C | O.Cl.NC(CC1=CC=C(OC2=CC=C(C=C3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC.C(=O)(OC(C)(C)C)N1C(CCC1)C(=O)O.C1(CCCCC1)N=C=NC1CCCCC1>>C(C)(C)(C)OC(=O)N1C(CCC1)C(NC(CC1=CC=C(C=C1)OC1=CC=C(C=C1)C=C1C(NC(S1)=O)=O)C(=O)OC)=O | O[C:29](=[O:30])[CH:31]1[CH2:32][CH2:33][CH2:34][N:35]1[C:36](=[O:37])[O:38][C:39]([CH3:40])([CH3:41])[CH3:42].[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][c:12]2[cH:13][cH:14][c:15]([CH:16]=[C:17]3[S:18][C:19](=[O:20])[NH:21][C:22]3=[O:23])[cH:24][cH:25]2)[cH:26][cH:27]1)[NH2:28]>>[CH3:1][O:2... | CC(C)(C)OC(=O)N1CCCC1C(=O)O.COC(=O)C(N)Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1 | COC(=O)C(Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1)NC(=O)C1CCCN1C(=O)OC(C)(C)C | null | null | C(C)(=O)OCC.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1NC(=O)C(=Cc2ccc(Oc3ccc(CCNC(=O)C4CCCN4)cc3)cc2)S1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13].[C:14]-[C:15](-[NH2;D1;+0:16])-[C:17](=[O;D1;H0:18])-[#8:19]-[C;D1;H3:20]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:16]-[C:15](-[C:14])-[C:17](=[O;D1;H0:18])-[#8:19]-[C;D1;... | 32.4 | [{"value": 32.4, "product": "C(C)(C)(C)OC(=O)N1C(CCC1)C(NC(CC1=CC=C(C=C1)OC1=CC=C(C=C1)C=C1C(NC(S1)=O)=O)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.1, "product": "C(C)(C)(C)OC(=O)N1C(CCC1)C(NC(CC1=CC=C(C=C1)OC1=CC=C(C=C1)C=C1C(NC(S1)=O)=O)C(=O)OC)=O", "details": "CALCULATEDPERCENTYIELD",... | null | null | 10 | HOUR | A solution of 5[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione hydrochloride (2.5 g, 5.76 mmol) and N-Boc-pyrolidin-2-carboxylic acid (1.238 g, 5.76 mmol) in dimethyl formamide (25 ml) was stirred for 60 minutes at 0° C. N,N′-Dicyclohexylcarbodiimide (1.423 g, 6.91 mmol) was added to it ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1CSCN1.C1CC[NH]C1 | HO- | C(C)(=O)OCC.CN(C=O)C | null | 10 | CC(C)(C)OC(=O)N1CCCC1C(=O)O.COC(=O)C(N)Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1>C(C)(=O)OCC.CN(C=O)C>COC(=O)C(Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1)NC(=O)C1CCCN1C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-964f5c140dda483dbe6b8a944fee6afc | CC(C)(C)OC(=O)N1CCCC1C(=O)O.COC(=O)C(N)Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1>>COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C1CCCN1C(=O)OC(C)(C)C | O.Cl.NC(CC1=CC=C(OC2=CC=C(CC3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC.C(C)(C)(C)OC(=O)N1C(CCC1)C(=O)O.C1(CCCCC1)N=C=NC1CCCCC1>>C(C)(C)(C)OC(=O)N1C(CCC1)C(NC(CC1=CC=C(C=C1)OC1=CC=C(C=C1)CC1C(NC(S1)=O)=O)C(=O)OC)=O | O[C:29](=[O:30])[CH:31]1[CH2:32][CH2:33][CH2:34][N:35]1[C:36](=[O:37])[O:38][C:39]([CH3:40])([CH3:41])[CH3:42].[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][c:12]2[cH:13][cH:14][c:15]([CH2:16][CH:17]3[S:18][C:19](=[O:20])[NH:21][C:22]3=[O:23])[cH:24][cH:25]2)[cH:26][cH:27]1)[NH2:28]>>[CH3:1][O:... | CC(C)(C)OC(=O)N1CCCC1C(=O)O.COC(=O)C(N)Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1 | COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C1CCCN1C(=O)OC(C)(C)C | null | null | C(C)(=O)OCC.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1NC(=O)C(Cc2ccc(Oc3ccc(CCNC(=O)C4CCCN4)cc3)cc2)S1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12])-[C:13].[C:14]-[C:15](-[NH2;D1;+0:16])-[C:17](=[O;D1;H0:18])-[#8:19]-[C;D1;H3:20]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:16]-[C:15](-[C:14])-[C:17](=[O;D1;H0:18])-[#8:19]-[C;D1;... | 51.2 | [{"value": 51.2, "product": "C(C)(C)(C)OC(=O)N1C(CCC1)C(NC(CC1=CC=C(C=C1)OC1=CC=C(C=C1)CC1C(NC(S1)=O)=O)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 5-[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione hydrochloride (2.03 g, 4.65 mmol) and N-t-butoxycarbonylpyrrolidin-2-carboxylic acid (1 g, 4.65 mmol) in N,N-dimethylformamide (20 ml) was stirred for 1 h at 0° C. N,N′-Dicyclohexylcarbodiimide (0.96 g, 4.65 mmol) was added to th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1CSCN1.C1CC[NH]C1 | HO- | C(C)(=O)OCC.CN(C=O)C | null | 2 | CC(C)(C)OC(=O)N1CCCC1C(=O)O.COC(=O)C(N)Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1>C(C)(=O)OCC.CN(C=O)C>COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C1CCCN1C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0b5223ecf85040698165df61d6191fd1 | CC(NC(=O)OC(C)(C)C)C(=O)O.COC(=O)C(N)Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1>>COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C(C)NC(=O)OC(C)(C)C | O.Cl.NC(CC1=CC=C(OC2=CC=C(CC3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC.C(C)(C)(C)OC(=O)NC(C(=O)O)C.C1(CCCCC1)N=C=NC1CCCCC1>>C(C)(C)(C)OC(=O)NC(C(=O)NC(CC1=CC=C(OC2=CC=C(CC3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC)C | O[C:29](=[O:30])[CH:31]([CH3:32])[NH:33][C:34](=[O:35])[O:36][C:37]([CH3:38])([CH3:39])[CH3:40].[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][c:12]2[cH:13][cH:14][c:15]([CH2:16][CH:17]3[S:18][C:19](=[O:20])[NH:21][C:22]3=[O:23])[cH:24][cH:25]2)[cH:26][cH:27]1)[NH2:28]>>[CH3:1][O:2][C:3](=[O:4])... | CC(NC(=O)OC(C)(C)C)C(=O)O.COC(=O)C(N)Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1 | COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C(C)NC(=O)OC(C)(C)C | null | null | C(C)(=O)OCC.O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1NC(=O)C(Cc2ccc(Oc3ccccc3)cc2)S1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[C:13]-[C:14](-[NH2;D1;+0:15])-[C:16](=[O;D1;H0:17])-[#8:18]-[C;D1;H3:19]>>[C:13]-[C:14](-[NH;D2;+0:15]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]... | 23 | [{"value": 23.0, "product": "C(C)(C)(C)OC(=O)NC(C(=O)NC(CC1=CC=C(OC2=CC=C(CC3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A solution of 5-[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione hydrochloride (2.3 g, 5.27 mmol) and 2-t-butoxycarbonylaminopropionic acid (0.997 g, 5.27 mmol) in tetrahydrofuran (20 ml) was stirred for 1 h at 0° C. N,N′-Dicyclohexylcarbodiimide (1.086 g, 5.27 mmol) was added to this solution... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1CSCN1 | HO- | C(C)(=O)OCC.O1CCCC1 | null | 1.5 | CC(NC(=O)OC(C)(C)C)C(=O)O.COC(=O)C(N)Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1>C(C)(=O)OCC.O1CCCC1>COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C(C)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9c8ede02f9314b8780028afe08414a5a | COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C(C)NC(=O)OC(C)(C)C>>COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C(C)N | C(C)(C)(C)OC(=O)NC(C(=O)NC(CC1=CC=C(OC2=CC=C(CC3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC)C.Cl>>Cl.NC(C(=O)NC(CC1=CC=C(OC2=CC=C(CC3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC)C | CC(C)(C)OC(=O)[NH:33][CH:31]([C:29]([NH:28][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][c:12]2[cH:13][cH:14][c:15]([CH2:16][CH:17]3[S:18][C:19](=[O:20])[NH:21][C:22]3=[O:23])[cH:24][cH:25]2)[cH:26][cH:27]1)=[O:30])[CH3:32]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11... | COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C(C)NC(=O)OC(C)(C)C | COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C(C)N | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1NC(=O)C(Cc2ccc(Oc3ccccc3)cc2)S1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]-[C:8](-[#8:9])=[O;D1;H0:10]>>[#8:9]-[C:8](=[O;D1;H0:10])-[C:7]-[#7:6]-[C:4](=[O;D1;H0:5])-[C:2](-[C;D1;H3:3])-[NH2;D1;+0:1] | 66.3 | [{"value": 66.3, "product": "Cl.NC(C(=O)NC(CC1=CC=C(OC2=CC=C(CC3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-[4-(4-(2-(2-t-butoxycarbonylaminopropanamido}2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione (1 g, 1.75 mmol) in dichloromethane (10 ml) was bubbled with HCl gas at −10° C. for 50 minutes. The excess HCl gas was removed by N2 bubbling and concentrated to dryness to afford the title compound ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1.C1CSCN1 | HO- | ClCCl | null | null | COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C(C)NC(=O)OC(C)(C)C>ClCCl>COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)C(C)N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-69940fd1468f471fa545f355ebf47133 | CC(NC(=O)OC(C)(C)C)C(=O)O.COC(=O)C(N)Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1>>COC(=O)C(Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1)NC(=O)C(C)NC(=O)OC(C)(C)C | O.Cl.NC(CC1=CC=C(OC2=CC=C(C=C3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC.C(C)(C)(C)OC(=O)NC(C(=O)O)C.C1(CCCCC1)N=C=NC1CCCCC1>>C(C)(C)(C)OC(=O)NC(C(=O)NC(CC1=CC=C(OC2=CC=C(C=C3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC)C | O[C:29](=[O:30])[CH:31]([CH3:32])[NH:33][C:34](=[O:35])[O:36][C:37]([CH3:38])([CH3:39])[CH3:40].[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][c:12]2[cH:13][cH:14][c:15]([CH:16]=[C:17]3[S:18][C:19](=[O:20])[NH:21][C:22]3=[O:23])[cH:24][cH:25]2)[cH:26][cH:27]1)[NH2:28]>>[CH3:1][O:2][C:3](=[O:4])[... | CC(NC(=O)OC(C)(C)C)C(=O)O.COC(=O)C(N)Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1 | COC(=O)C(Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1)NC(=O)C(C)NC(=O)OC(C)(C)C | null | null | C(C)(=O)OCC.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1NC(=O)C(=Cc2ccc(Oc3ccccc3)cc2)S1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12].[C:13]-[C:14](-[NH2;D1;+0:15])-[C:16](=[O;D1;H0:17])-[#8:18]-[C;D1;H3:19]>>[C:13]-[C:14](-[NH;D2;+0:15]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6](=[O;D1;H0:7])-[#8:8]... | 36.3 | [{"value": 36.3, "product": "C(C)(C)(C)OC(=O)NC(C(=O)NC(CC1=CC=C(OC2=CC=C(C=C3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A solution of 5-[4-(4-(2-amino-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione hydrochloride (2 g, 4.6 mmol) and 2-t-butoxycarbonylamino propionic acid (0.87 g, 4.6 mmol) in dimethyl formamide (10 ml) was stirred for 1 h at 0° C. N,N′-Dicyclohexylcarbodiimide (1.139 g, 5.5 mmol) was added to this solut... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1CSCN1 | HO- | C(C)(=O)OCC.CN(C=O)C | null | 2 | CC(NC(=O)OC(C)(C)C)C(=O)O.COC(=O)C(N)Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1>C(C)(=O)OCC.CN(C=O)C>COC(=O)C(Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1)NC(=O)C(C)NC(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9e01c3eb0ed740a29320f8d952f36727 | COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)CNC(=O)OC(C)(C)C>>COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)CN | C(C)(C)(C)OC(=O)NCC(=O)NC(CC1=CC=C(OC2=CC=C(CC3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC.Cl>>Cl.NCC(=O)NC(CC1=CC=C(OC2=CC=C(CC3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC | CC(C)(C)OC(=O)[NH:32][CH2:31][C:29]([NH:28][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][c:12]2[cH:13][cH:14][c:15]([CH2:16][CH:17]3[S:18][C:19](=[O:20])[NH:21][C:22]3=[O:23])[cH:24][cH:25]2)[cH:26][cH:27]1)=[O:30]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][c:12]2[... | COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)CNC(=O)OC(C)(C)C | COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)CN | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1NC(=O)C(Cc2ccc(Oc3ccccc3)cc2)S1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[C:6]-[C:7](-[#8:8])=[O;D1;H0:9]>>[#8:8]-[C:7](=[O;D1;H0:9])-[C:6]-[#7:5]-[C:3](=[O;D1;H0:4])-[C:2]-[NH2;D1;+0:1] | 78.8 | [{"value": 78.8, "product": "Cl.NCC(=O)NC(CC1=CC=C(OC2=CC=C(CC3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-[4-(4-(2-(2-t-butoxycarbonylaminoacetamido)-2-methoxycarbonylethyl)phenoxy)benzyl]thiazolidin-2,4-dione (0.73 g, 1.31 mmol) in dichloromethane (30 ml) was bubbled with HCl gas at −10° C. for 1.25 h. The excess HCl gas was removed by N2 bubbling and the solvent was removed by distillation to provide the ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1.C1CSCN1 | HO- | ClCCl | null | null | COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)CNC(=O)OC(C)(C)C>ClCCl>COC(=O)C(Cc1ccc(Oc2ccc(CC3SC(=O)NC3=O)cc2)cc1)NC(=O)CN |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-25127b0bf1854ea0bc85f57270ceb0a7 | COC(=O)C(Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1)NC(=O)C(CCSC)NC(=O)OC(C)(C)C>>COC(=O)C(Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1)NC(=O)C(N)CCSC | CSCCC(C(=O)NC(CC1=CC=C(OC2=CC=C(C=C3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC)NC(=O)OC(C)(C)C.Cl>>Cl.CSCCC(C(=O)NC(CC1=CC=C(OC2=CC=C(C=C3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC)N | CC(C)(C)OC(=O)[NH:32][CH:31]([C:29]([NH:28][CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][c:12]2[cH:13][cH:14][c:15]([CH:16]=[C:17]3[S:18][C:19](=[O:20])[NH:21][C:22]3=[O:23])[cH:24][cH:25]2)[cH:26][cH:27]1)=[O:30])[CH2:33][CH2:34][S:35][CH3:36]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH... | COC(=O)C(Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1)NC(=O)C(CCSC)NC(=O)OC(C)(C)C | COC(=O)C(Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1)NC(=O)C(N)CCSC | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C1NC(=O)C(=Cc2ccc(Oc3ccccc3)cc2)S1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]-[C:8](-[#8:9])=[O;D1;H0:10]>>[#8:9]-[C:8](=[O;D1;H0:10])-[C:7]-[#7:6]-[C:4](=[O;D1;H0:5])-[C:2](-[C:3])-[NH2;D1;+0:1] | 80.6 | [{"value": 80.6, "product": "Cl.CSCCC(C(=O)NC(CC1=CC=C(OC2=CC=C(C=C3C(NC(S3)=O)=O)C=C2)C=C1)C(=O)OC)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 5-[4-(4-(2-(4-methylthio-2-t-butoxycarbonylaminobutyramido)-2-methoxycarbonylethyl)phenoxy)benzylidene]thiazolidin-2,4-dione (1.38 g, 2.2 mmol) in dichloromethane (30 ml) was bubbled with HCl gas at −10° C. for 80 minutes. The excess HCl gas was removed by N2 bubbling and the solvent was removed by distil... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccccc1.C1CSCN1 | HO- | ClCCl | null | null | COC(=O)C(Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1)NC(=O)C(CCSC)NC(=O)OC(C)(C)C>ClCCl>COC(=O)C(Cc1ccc(Oc2ccc(C=C3SC(=O)NC3=O)cc2)cc1)NC(=O)C(N)CCSC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b693a864a5f84c91904645550a8b9dac | COC(=O)c1ccc(C=O)cc1.c1ccc([P+](c2ccccc2)(c2ccccc2)C2CC2)cc1>>COC(=O)c1ccc(C=C2CC2)cc1 | O.[Br-].C1(CC1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.[H-].[Na+].COC(=O)C1=CC=C(C=C1)C=O>>C1(CC1)=CC1=CC=C(C(=O)OC)C=C1 | O=[CH:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:14][cH:13]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH:10]2[CH2:11][CH2:12]2)cc1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]=[C:10]2[CH2:11][CH2:12]2)[cH:13][cH:14]1 | COC(=O)c1ccc(C=O)cc1.c1ccc([P+](c2ccccc2)(c2ccccc2)C2CC2)cc1 | COC(=O)c1ccc(C=C2CC2)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | bd381618bc151c1640636a375a39e59b35fa6d8a00d5cfbbe1b09d2ed0b3fba6 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=C1CC1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]1-[C:6]-[CH;D3;+0:7]-1-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[c:3]:[c:2](-[CH;D2;+0:1]=[C;H0;D3;+0:7]1-[C:5]-[C:6]-1):[c:4] | 69.8 | [{"value": 69.8, "product": "C1(CC1)=CC1=CC=C(C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 2 | HOUR | To a suspension of sodium hydride (60%, 0.27 g) in tetrahydrofuran (40 mL) was added cyclopropyltriphenylphosphonium bromide (2.6 g), and the mixture was stirred at 70° C. for 2 hours. To the reaction mixture was added methyl terephthalaldehydate (1.0 g), and the mixture was stirred at 70° C. for 7 days. Water was adde... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CC1 | C1CC1 | c1ccccc1.C1CC1 | HO- | O1CCCC1 | 70 | 2 | COC(=O)c1ccc(C=O)cc1.c1ccc([P+](c2ccccc2)(c2ccccc2)C2CC2)cc1>O1CCCC1>COC(=O)c1ccc(C=C2CC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-777da998342d4afdbf69846fb21072a8 | COC(=O)c1ccc(C=C2CC2)cc1>>OCc1ccc(C=C2CC2)cc1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].C1(CC1)=CC1=CC=C(C(=O)OC)C=C1.O>>C1(CC1)=CC1=CC=C(CO)C=C1 | CO[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6]([CH:7]=[C:8]2[CH2:9][CH2:10]2)[cH:11][cH:12]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[C:8]2[CH2:9][CH2:10]2)[cH:11][cH:12]1 | COC(=O)c1ccc(C=C2CC2)cc1 | OCc1ccc(C=C2CC2)cc1 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C(=C1CC1)c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 101.3 | [{"value": 101.3, "product": "C1(CC1)=CC1=CC=C(CO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a suspension of lithium aluminum hydride (0.16 g) in tetrahydrofuran (30 mL) was added methyl 4-(cyclopropylidenemethyl)benzoate (0.80 g), and the mixture was stirred at room temperature for 5 hours. Water (0.4 mL) was added to the reaction mixture, and the mixture was stirred for 3 days. Insoluble materials were re... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.C1CC1 | Other | O1CCCC1 | null | 5 | COC(=O)c1ccc(C=C2CC2)cc1>O1CCCC1>OCc1ccc(C=C2CC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9ebaaf178676404ebfef3fc9396de50d | 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(C=C2CC2)cc1>>CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(C=C3CC3)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | CC1=C(C(NN1)=O)CC1=CC=C(C=C1)C=C1CC1.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>>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=C1CC1 | 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]([CH:21]=[C:22]2[CH2:23][CH2:24]2)[cH:25][cH:26]1>>[CH3:1][C:... | 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(C=C2CC2)cc1 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(C=C3CC3)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 | C(=C1CC1)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... | 16.2 | [{"value": 16.2, "product": "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=C1CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 8 | HOUR | To a suspension of 5-methyl-4-{[4-(cyclopropylidenemethyl)phenyl]methyl}-1,2-dihydro-3H-pyrazol-3-one (0.026 g) and acetobromo-α-D-glucose (0.049 g) in tetrahydrofuran was added silver carbonate (0.036 g), and the mixture was stirred at 60° C. overnight under light shielding. The reaction mixture was purified by column... | 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.C1CC1 | HBr | C([O-])([O-])=O.[Ag+2].O1CCCC1 | 60 | 8 | 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(C=C2CC2)cc1>C([O-])([O-])=O.[Ag+2].O1CCCC1>CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(C=C3CC3)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-19e9a998f28946868815e06a318ccf88 | Brc1ccc(C2CC2)cc1.CN(C)C=O>>O=Cc1ccc(C2CC2)cc1 | [Cl-].[NH4+].C(C)(C)(C)[Li].C1(CC1)C1=CC=C(C=C1)Br.CN(C=O)C>>C1(CC1)C1=CC=C(C=O)C=C1 | Br[c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][CH2:9]2)[cH:10][cH:11]1.CN(C)[CH:2]=[O:1]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][CH2:9]2)[cH:10][cH:11]1 | Brc1ccc(C2CC2)cc1.CN(C)C=O | O=Cc1ccc(C2CC2)cc1 | null | null | O1CCCC1 | C-C Coupling | Bouveault aldehyde synthesis | 4664d189e1ff40b394aee0a7d0943c7bfc06c1f81f238cff6865649dda594153 | afd09ced98f25d311f21cc04ba6a50fe7e5516de47e17484683ded13d323b1b2 | c1ccc(C2CC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-N(-C)-[CH;D2;+0:6]=[O;D1;H0:7]>>[O;D1;H0:7]=[CH;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | -78 | CELSIUS | 30 | MINUTE | To a solution of 4-bromostylene (1.83 g) in dichloromethane (5 mL) was added diethylzinc (1 mol/L, 30 mL) under an argon atmosphere at 0° C., and the mixture was stirred at the same temperature for 10 minutes. Chloroiodomethane (4.3 mL) was added to the mixture, and the mixture was warmed to room temperature and stirre... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Aldehyde | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC1 | HBr | O1CCCC1 | -78 | 0.5 | Brc1ccc(C2CC2)cc1.CN(C)C=O>O1CCCC1>O=Cc1ccc(C2CC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-621039449c2a4a8292dc2cf8bcf28ed2 | O=Cc1ccc(C2CC2)cc1>>OCc1ccc(C2CC2)cc1 | O.C1(CC1)C1=CC=C(C=O)C=C1.[BH4-].[Li+]>>C1(CC1)C1=CC=C(CO)C=C1 | [O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][CH2:9]2)[cH:10][cH:11]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH:7]2[CH2:8][CH2:9]2)[cH:10][cH:11]1 | O=Cc1ccc(C2CC2)cc1 | OCc1ccc(C2CC2)cc1 | null | null | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(C2CC2)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 95.9 | [{"value": 95.9, "product": "C1(CC1)C1=CC=C(CO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 4-cyclopropylbenzaldehyde (0.71 g) in methanol (10 mL) was added lithium borohydride (2 mol/L tetrahydrofuran solution, 3.7 mL), and the mixture was warmed to room temperature and stirred for 30 minutes. To the reaction mixture was added water, and the mixture was extracted with diethyl ether. The orga... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1.C1CC1 | null | CO | null | 0.5 | O=Cc1ccc(C2CC2)cc1>CO>OCc1ccc(C2CC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6e4a81ed99724d89ab0593aba47b36bc | CCC=O.CCP(=O)(CC)Cc1ccc(C(=O)OC)cc1>>CC/C=C/c1ccc(C(=O)OC)cc1 | [Cl-].[NH4+].C(C)P(=O)(CC)CC1=CC=C(C(=O)OC)C=C1.[H-].[Na+].C(CC)=O>>C(=C\CC)/C1=CC=C(C(=O)OC)C=C1 | O=[CH:3][CH2:2][CH3:1].CCP(=O)(CC)[CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[O:11][CH3:12])[cH:13][cH:14]1>>[CH3:1][CH2:2]/[CH:3]=[CH:4]/[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[O:11][CH3:12])[cH:13][cH:14]1 | CCC=O.CCP(=O)(CC)Cc1ccc(C(=O)OC)cc1 | CC/C=C/c1ccc(C(=O)OC)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 43d4e2f03e758941ee99f59641d5d56e6475fe935434d251d75d5cdebbe19869 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | c1ccccc1 | C-C-P(=O)(-C-C)-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].O=[CH;D2;+0:5]-[C:6]-[C;D1;H3:7]>>[C;D1;H3:7]-[C:6]/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | To a suspension of sodium hydride (60%, 0.97 g) in tetrahydrofuran (80 mL) was added methyl 4-(diethylphosphorylmethyl)benzoate (5.8 g) at 0° C., and the mixture was stirred for 30 minutes. To the reaction mixture was added a solution of propionaldehyde (1.6 mL) in tetrahydrofuran (10 mL), and the mixture was stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | null | null | c1ccccc1 | HO- | O1CCCC1 | null | 0.5 | CCC=O.CCP(=O)(CC)Cc1ccc(C(=O)OC)cc1>O1CCCC1>CC/C=C/c1ccc(C(=O)OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ca3864fed8fc4967bdbb8ce498ef21c7 | CCC=Cc1ccc(C(=O)OC)cc1>>CC/C=C/c1ccc(CO)cc1 | C(=CCC)C1=CC=C(C(=O)OC)C=C1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O.O>>C(=C\CC)/C1=CC=C(CO)C=C1 | CO[C:9]([c:8]1[cH:7][cH:6][c:5]([CH:4]=[CH:3][CH2:2][CH3:1])[cH:12][cH:11]1)=[O:10]>>[CH3:1][CH2:2]/[CH:3]=[CH:4]/[c:5]1[cH:6][cH:7][c:8]([CH2:9][OH:10])[cH:11][cH:12]1 | CCC=Cc1ccc(C(=O)OC)cc1 | CC/C=C/c1ccc(CO)cc1 | null | null | C(C)OCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 89.1 | [{"value": 89.1, "product": "C(=C\\CC)/C1=CC=C(CO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | To a suspension of lithium aluminum hydride (1.2 g) in diethyl ether (100 mL) was added a solution of methyl 4-(but-1-en-1-yl)benzoate (2.5 g) in diethyl ether (20 mL) at 0° C., and the mixture was heated under reflux for 30 mixture. After the reaction mixture was cooled to 0° C., to the mixture were added water (1.2 m... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | C(C)OCC | 0 | null | CCC=Cc1ccc(C(=O)OC)cc1>C(C)OCC>CC/C=C/c1ccc(CO)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e24f573036ff4a2aaa16817ca2bb8277 | COCCl.OCc1ccc(Br)cc1>>COCOCc1ccc(Br)cc1 | O.BrC1=CC=C(CO)C=C1.C(C)(C)N(CC)C(C)C.COCCl>>BrC1=CC=C(C=C1)COCOC | Cl[CH2:3][O:2][CH3:1].[OH:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1>>[CH3:1][O:2][CH2:3][O:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1 | COCCl.OCc1ccc(Br)cc1 | COCOCc1ccc(Br)cc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 27244342195fcd168f26a709ba63fe92c20aa8622e0ab7a8f8d1433cf4454d5d | 6b7bcf6411652db3d69b48a8c20d1194484df28a33661f5a192e999e8e5bbb75 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C;D1;H3:3].[OH;D1;+0:4]-[C:5]-[c:6]>>[C;D1;H3:3]-[#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[C:5]-[c:6] | 86.7 | [{"value": 86.7, "product": "BrC1=CC=C(C=C1)COCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a solution of 4-bromobenzyl alcohol (2.8 g) and diisopropylethylamine (2.5 g) in dichloromethane (30 mL) was added chloromethyl methyl ether (1.3 g) at 0° C., and the mixture was stirred at room temperature for 14 hours. To the reaction mixture was water, and the mixture was extracted diethyl ether. The organic laye... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Primary alcohol | Ether.Ether | null | null | c1ccccc1 | HCl | ClCCl | null | 14 | COCCl.OCc1ccc(Br)cc1>ClCCl>COCOCc1ccc(Br)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bf427509761f45f6aaacfa11f5e1b9a1 | CC(C)OB(OC(C)C)OC(C)C.COCOCc1ccc(Br)cc1>>COCOCc1ccc(OB(O)O)cc1 | Cl.B(OC(C)C)(OC(C)C)OC(C)C.BrC1=CC=C(C=C1)COCOC.C(CCC)[Li]>>COCOCC1=CC=C(C=C1)OB(O)O | CC(C)[O:10][B:11]([O:12]C(C)C)[O:13]C(C)C.Br[c:9]1[cH:8][cH:7][c:6]([CH2:5][O:4][CH2:3][O:2][CH3:1])[cH:15][cH:14]1>>[CH3:1][O:2][CH2:3][O:4][CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][B:11]([OH:12])[OH:13])[cH:14][cH:15]1 | CC(C)OB(OC(C)C)OC(C)C.COCOCc1ccc(Br)cc1 | COCOCc1ccc(OB(O)O)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | e9dbfb9f314e618f498ba931f950b90cc87acea41f31fcecb8d08ba23aa7f8e1 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].C-C(-C)-[O;H0;D2;+0:6]-[#5:7](-[O;H0;D2;+0:8]-C(-C)-C)-[O;H0;D2;+0:9]-C(-C)-C>>[OH;D1;+0:8]-[#5:7](-[OH;D1;+0:9])-[O;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 90.8 | [{"value": 90.8, "product": "COCOCC1=CC=C(C=C1)OB(O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 1-bromo-4-[(methoxymethyloxy)methyl]benzene (3.0 g) in tetrahydrofuran (52 mL) was added n-butyllithium (1.6 mol/L hexane solution, 9.3 mL) at −78° C., and the mixture was stirred for 30 minutes. To the reaction mixture was added triisopropyl borate (2.6 g), and the mixture was stirred at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | O1CCCC1 | null | 0.5 | CC(C)OB(OC(C)C)OC(C)C.COCOCc1ccc(Br)cc1>O1CCCC1>COCOCc1ccc(OB(O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-260a63fadb674591b1c496508b6d04c3 | Brc1nccs1.COCOCc1ccc(OB(O)O)cc1>>COCOCc1ccc(-c2nccs2)cc1 | COCOCC1=CC=C(C=C1)OB(O)O.BrC=1SC=CN1.[F-].[Cs+]>>COCOCC1=CC=C(C=C1)C=1SC=CN1 | Br[c:10]1[n:11][cH:12][cH:13][s:14]1.OB(O)O[c:9]1[cH:8][cH:7][c:6]([CH2:5][O:4][CH2:3][O:2][CH3:1])[cH:16][cH:15]1>>[CH3:1][O:2][CH2:3][O:4][CH2:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[n:11][cH:12][cH:13][s:14]2)[cH:15][cH:16]1 | Brc1nccs1.COCOCc1ccc(OB(O)O)cc1 | COCOCc1ccc(-c2nccs2)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC.C(C)O | C-C Coupling | OtherReaction | c5d70f44da54f3e70cb2853a91e1281ef6956874f04660e612a73059bc40890b | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2nccs2)cc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.O-B(-O)-O-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1):[c:9]:[c:10] | 46.5 | [{"value": 46.5, "product": "COCOCC1=CC=C(C=C1)C=1SC=CN1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 24 | HOUR | To a solution of 1-bromo-4-[(methoxymethyloxy)methyl]benzene (3.0 g) in tetrahydrofuran (52 mL) was added n-butyllithium (1.6 mol/L hexane solution, 9.3 mL) at −78° C., and the mixture was stirred for 30 minutes. To the reaction mixture was added triisopropyl borate (2.6 g), and the mixture was stirred at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cscn1.c1ccccc1 | c1ccccc1.c1cscn1 | c1ccccc1.c1cscn1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC.C(C)O | 85 | 24 | Brc1nccs1.COCOCc1ccc(OB(O)O)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC.C(C)O>COCOCc1ccc(-c2nccs2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ba1b19d3ae524c2aa76779742eed3d65 | COCOCc1ccc(-c2nccs2)cc1>>OCc1ccc(-c2nccs2)cc1 | O.Cl.COCOCC1=CC=C(C=C1)C=1SC=CN1.Cl>>S1C(=NC=C1)C1=CC=C(CO)C=C1 | COC[O:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][s:11]2)[cH:12][cH:13]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][cH:10][s:11]2)[cH:12][cH:13]1 | COCOCc1ccc(-c2nccs2)cc1 | OCc1ccc(-c2nccs2)cc1 | null | null | C(C)O | Reduction | Cleavage of alkoxy ethers to alcohols | c466c3bec39e9af8d3c14d52e5e6f58679d038f05bc956e4b63094a922799541 | a4561cbdd42f56679299e19ea8b11070a39a15f6a95fb8a877e677f11b7ff57f | c1ccc(-c2nccs2)cc1 | C-O-C-[O;H0;D2;+0:1]-[C:2]-[c:3]>>[OH;D1;+0:1]-[C:2]-[c:3] | 50.8 | [{"value": 50.8, "product": "S1C(=NC=C1)C1=CC=C(CO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 5 | HOUR | To a solution of 1-bromo-4-[(methoxymethyloxy)methyl]benzene (3.0 g) in tetrahydrofuran (52 mL) was added n-butyllithium (1.6 mol/L hexane solution, 9.3 mL) at −78° C., and the mixture was stirred for 30 minutes. To the reaction mixture was added triisopropyl borate (2.6 g), and the mixture was stirred at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol | null | null | c1ccccc1.c1cscn1 | HO- | C(C)O | 50 | 5 | COCOCc1ccc(-c2nccs2)cc1>C(C)O>OCc1ccc(-c2nccs2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9ea8bc6bb4054a54a4711a5394da890f | CCOC(=O)CP(=O)(OCC)OCC.CCOC(OCC)c1ccc(C=O)cc1>>CCOC(=O)C=Cc1ccc(C(OCC)OCC)cc1 | [Cl-].[NH4+].CCOC(C1=CC=C(C=C1)C=O)OCC.C(C)OP(=O)(OCC)CC(=O)OCC.[H-].[Na+]>>C(C)OC(C1=CC=C(C=CC(=O)OCC)C=C1)OCC | CCOP(=O)(OCC)[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].O=[CH:7][c:8]1[cH:9][cH:10][c:11]([CH:12]([O:13][CH2:14][CH3:15])[O:16][CH2:17][CH3:18])[cH:19][cH:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][c:8]1[cH:9][cH:10][c:11]([CH:12]([O:13][CH2:14][CH3:15])[O:16][CH2:17][CH3:18])[cH:19][cH:20]1 | CCOC(=O)CP(=O)(OCC)OCC.CCOC(OCC)c1ccc(C=O)cc1 | CCOC(=O)C=Cc1ccc(C(OCC)OCC)cc1 | null | null | O.O1CCCC1 | C-C Coupling | Wittig with Phosphonium | a86984aeb4a9963534e0b081b0ecca18455fda1775f36ce168d1ca4cf966df3e | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccccc1 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].O=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH;D2;+0:1]=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | 10 | MINUTE | To a solution of ethyl diethylphosphonoacetate (4.4 mL) in tetrahydrofuran (40 mL) was added sodium hydride (60%, 0.88 g) at 0° C., and the mixture was stirred for 10 minutes. To the reaction mixture was added a solution of terephthalaldehyde mono-(diethyl acetal) (4.2 g) in tetrahydrofuran (10 mL), and the mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | null | null | c1ccccc1 | HO- | O.O1CCCC1 | null | 0.166667 | CCOC(=O)CP(=O)(OCC)OCC.CCOC(OCC)c1ccc(C=O)cc1>O.O1CCCC1>CCOC(=O)C=Cc1ccc(C(OCC)OCC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5594bc4ab0f641049337d59474f1dcda | CCOC(=O)C=Cc1ccc(C(OCC)OCC)cc1>>CCOC(OCC)c1ccc(CCCO)cc1 | C(C)OC(C1=CC=C(C=CC(=O)OCC)C=C1)OCC>>C(C)OC(C1=CC=C(C=C1)CCCO)OCC | CCO[C:14]([CH:13]=[CH:12][c:11]1[cH:10][cH:9][c:8]([CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7])[cH:17][cH:16]1)=[O:15]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[c:8]1[cH:9][cH:10][c:11]([CH2:12][CH2:13][CH2:14][OH:15])[cH:16][cH:17]1 | CCOC(=O)C=Cc1ccc(C(OCC)OCC)cc1 | CCOC(OCC)c1ccc(CCCO)cc1 | null | [Pt] | O1CCCC1 | Reduction | OtherReaction | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D2;+0:3]=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7] | 94.6 | [{"value": 94.6, "product": "C(C)OC(C1=CC=C(C=C1)CCCO)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | To a solution of ethyl diethylphosphonoacetate (4.4 mL) in tetrahydrofuran (40 mL) was added sodium hydride (60%, 0.88 g) at 0° C., and the mixture was stirred for 10 minutes. To the reaction mixture was added a solution of terephthalaldehyde mono-(diethyl acetal) (4.2 g) in tetrahydrofuran (10 mL), and the mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | [Pt].O1CCCC1 | null | 10 | CCOC(=O)C=Cc1ccc(C(OCC)OCC)cc1>[Pt].O1CCCC1>CCOC(OCC)c1ccc(CCCO)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f8d46507f5dc462fa621f54e904a8352 | BrCc1ccccc1.CCOC(OCC)c1ccc(CCCO)cc1>>CCOC(OCC)c1ccc(CCCOCc2ccccc2)cc1 | O.C(C1=CC=CC=C1)Br.C(C)OC(C1=CC=C(C=C1)CCCO)OCC.[H-].[Na+]>>C(C)OC(C1=CC=C(C=C1)CCCOCC1=CC=CC=C1)OCC | Br[CH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[c:8]1[cH:9][cH:10][c:11]([CH2:12][CH2:13][CH2:14][OH:15])[cH:23][cH:24]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[c:8]1[cH:9][cH:10][c:11]([CH2:12][CH2:13][CH2:14][O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21]... | BrCc1ccccc1.CCOC(OCC)c1ccc(CCCO)cc1 | CCOC(OCC)c1ccc(CCCOCc2ccccc2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | c1ccc(CCCOCc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 5 | MINUTE | To a solution of ethyl diethylphosphonoacetate (4.4 mL) in tetrahydrofuran (40 mL) was added sodium hydride (60%, 0.88 g) at 0° C., and the mixture was stirred for 10 minutes. To the reaction mixture was added a solution of terephthalaldehyde mono-(diethyl acetal) (4.2 g) in tetrahydrofuran (10 mL), and the mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C=O)C | null | 0.083333 | BrCc1ccccc1.CCOC(OCC)c1ccc(CCCO)cc1>CN(C=O)C>CCOC(OCC)c1ccc(CCCOCc2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-77a21fdd8bff4c069bfb526f3490207b | CCOC(OCC)c1ccc(CCCOCc2ccccc2)cc1>>OCc1ccc(CCCOCc2ccccc2)cc1 | O.C(C)OC(C1=CC=C(C=C1)CCCOCC1=CC=CC=C1)OCC.Cl>>C(C1=CC=CC=C1)OCCCC1=CC=C(CO)C=C1 | CCO[CH:2]([O:1]CC)[c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19]1 | CCOC(OCC)c1ccc(CCCOCc2ccccc2)cc1 | OCc1ccc(CCCOCc2ccccc2)cc1 | null | null | O1CCCC1 | Reduction | OtherReaction | c466c3bec39e9af8d3c14d52e5e6f58679d038f05bc956e4b63094a922799541 | a4561cbdd42f56679299e19ea8b11070a39a15f6a95fb8a877e677f11b7ff57f | c1ccc(CCCOCc2ccccc2)cc1 | C-C-O-[CH;D3;+0:1](-[O;H0;D2;+0:2]-C-C)-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 74.1 | [{"value": 74.1, "product": "C(C1=CC=CC=C1)OCCCC1=CC=C(CO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of ethyl diethylphosphonoacetate (4.4 mL) in tetrahydrofuran (40 mL) was added sodium hydride (60%, 0.88 g) at 0° C., and the mixture was stirred for 10 minutes. To the reaction mixture was added a solution of terephthalaldehyde mono-(diethyl acetal) (4.2 g) in tetrahydrofuran (10 mL), and the mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | 1 | CCOC(OCC)c1ccc(CCCOCc2ccccc2)cc1>O1CCCC1>OCc1ccc(CCCOCc2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-455c633b370b4a5898ab60ef54ef475f | CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.O=c1[nH][nH]c(C(F)(F)F)c1Cc1ccc(CCCOCc2ccccc2)cc1>>CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(CCCOCc3ccccc3)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | C(C1=CC=CC=C1)OCCCC1=CC=C(C=C1)CC=1C(NNC1C(F)(F)F)=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([O-])([O-])=O.[K+].[K+]>>C(C1=CC=CC=C1)OCCCC1=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 | Br[C@H:8]1[O:7][C@H:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])[C@@H:47]([O:48][C:49]([CH3:50])=[O:51])[C@H:42]([O:43][C:44]([CH3:45])=[O:46])[C@H:37]1[O:38][C:39]([CH3:40])=[O:41].[O:9]=[c:10]1[nH:11][nH:12][c:13]([C:14]([F:15])([F:16])[F:17])[c:18]1[CH2:19][c:20]1[cH:21][cH:22][c:23]([CH2:24][CH2:25][CH2:26][O:27][CH2:28][c... | CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.O=c1[nH][nH]c(C(F)(F)F)c1Cc1ccc(CCCOCc2ccccc2)cc1 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(CCCOCc3ccccc3)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 49b04419fad6ce95036469eff0b0bfaaabc2fb3bd31dcfbbcd47a76a3bff025b | 5cef8b32be1a1b6849554821131ec7ae3bfda59406cde9d9abe4b3a7d689dd3d | c1ccc(COCCCc2ccc(Cc3c[nH]nc3O[C@H]3CCCCO3)cc2)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:13](-[F;D1;H0:14])(-[F;D1;H0:15])-[F;D1;H0:16]):[#7;a:17]:[nH;D2;+0:18]:[c;H0;D3;+0:19]:1=[O;H0;D1;+0:20]>>[C:10]-[c:11]1:[c:12](-[C:13](-[F;D1;H0:14])(-[F;D1;H0:15])-[F;D1;H0:16]):[#7;a:17]:[n;H0;D2;+0:18]:[... | 41.8 | [{"value": 41.8, "product": "C(C1=CC=CC=C1)OCCCC1=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", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 20 | HOUR | To a solution of 4-({4-[3-(benzyloxy)propyl]phenyl}methyl)-5-trifluoromethyl-1,2-dihydro-3H-pyrazole-3-one (0.83 g) and acetobromo-α-D-glucose (1.5 g) in acetonitrile (12 mL) was added potassium carbonate (0.55 g), and the mixture was stirred at 60° C. for 20 hours. Insoluble materials were removed by filtration, and t... | 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.c1ccccc1 | HBr | C(C)#N | 60 | 20 | CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.O=c1[nH][nH]c(C(F)(F)F)c1Cc1ccc(CCCOCc2ccccc2)cc1>C(C)#N>CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C(F)(F)F)c2Cc2ccc(CCCOCc3ccccc3)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-646484b9805f4ab1801c6600e812a249 | CC(C)[P+](c1ccccc1)(c1ccccc1)c1ccccc1.COC(=O)c1ccc(C=O)cc1>>COC(=O)c1ccc(C=C(C)C)cc1 | [Cl-].[NH4+].C(CCC)[Li].[I-].C(C)(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.COC(=O)C1=CC=C(C=C1)C=O>>CC(=CC1=CC=C(C(=O)OC)C=C1)C | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH:10]([CH3:11])[CH3:12])cc1.O=[CH:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:14][cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]=[C:10]([CH3:11])[CH3:12])[cH:13][cH:14]1 | CC(C)[P+](c1ccccc1)(c1ccccc1)c1ccccc1.COC(=O)c1ccc(C=O)cc1 | COC(=O)c1ccc(C=C(C)C)cc1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[CH;D3;+0:6](-[C;D1;H3:7])-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C;D1;H3:5]-[C;H0;D3;+0:6](-[C;D1;H3:7])=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 88.9 | [{"value": 88.9, "product": "CC(=CC1=CC=C(C(=O)OC)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a suspension of isopropyltriphenylphosphonium iodide (9.5 g) in tetrahydrofuran (90 mL) was added n-butyllithium (1.5 mol/L hexane solution, 15 mL) at 0° C., and the mixture was stirred for 15 minutes. To the reaction mixture was added a solution of methyl terephthalaldehydate (3.3 g) in tetrahydrofuran (10 mL), and... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1 | HO- | O1CCCC1 | null | 0.25 | CC(C)[P+](c1ccccc1)(c1ccccc1)c1ccccc1.COC(=O)c1ccc(C=O)cc1>O1CCCC1>COC(=O)c1ccc(C=C(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e354b1f01bf5458aaf4bf38d80edc405 | COC(=O)c1ccc(C=C(C)C)cc1>>CC(C)=Cc1ccc(CO)cc1 | CC(=CC1=CC=C(C(=O)OC)C=C1)C.O.[OH-].[Na+].O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>CC(=CC1=CC=C(CO)C=C1)C | CO[C:9]([c:8]1[cH:7][cH:6][c:5]([CH:4]=[C:2]([CH3:1])[CH3:3])[cH:12][cH:11]1)=[O:10]>>[CH3:1][C:2]([CH3:3])=[CH:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][OH:10])[cH:11][cH:12]1 | COC(=O)c1ccc(C=C(C)C)cc1 | CC(C)=Cc1ccc(CO)cc1 | null | null | C(C)OCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 96.6 | [{"value": 96.6, "product": "CC(=CC1=CC=C(CO)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a suspension of isopropyltriphenylphosphonium iodide (9.5 g) in tetrahydrofuran (90 mL) was added n-butyllithium (1.5 mol/L hexane solution, 15 mL) at 0° C., and the mixture was stirred for 15 minutes. To the reaction mixture was added a solution of methyl terephthalaldehydate (3.3 g) in tetrahydrofuran (10 mL), and... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | C(C)OCC | 0 | 0.5 | COC(=O)c1ccc(C=C(C)C)cc1>C(C)OCC>CC(C)=Cc1ccc(CO)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c7e2282149994952b0a66f32c7b5a32d | BrC(Br)(Br)Br.CC(C)=Cc1ccc(CO)cc1>>CC(C)=Cc1ccc(CBr)cc1 | O.CC(=CC1=CC=C(CO)C=C1)C.C(Br)(Br)(Br)Br.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>CC(=CC1=CC=C(CBr)C=C1)C | BrC(Br)(Br)[Br:10].O[CH2:9][c:8]1[cH:7][cH:6][c:5]([CH:4]=[C:2]([CH3:1])[CH3:3])[cH:12][cH:11]1>>[CH3:1][C:2]([CH3:3])=[CH:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][Br:10])[cH:11][cH:12]1 | BrC(Br)(Br)Br.CC(C)=Cc1ccc(CO)cc1 | CC(C)=Cc1ccc(CBr)cc1 | null | null | ClCCl | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | c1ccccc1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 3.5 | HOUR | To a solution of 4-(2-methylprop-1-en-1-yl)benzyl alcohol (0.60 g) and carbon tetrabromide (1.2 g) in dichloromethane (12 mL) was added triphenylphosphine (0.97 g) at 0° C., and the mixture was stirred at room temperature for 3.5 hours. To the reaction mixture was added water, and the mixture was extracted with hexane.... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | c1ccccc1 | HBr | ClCCl | null | 3.5 | BrC(Br)(Br)Br.CC(C)=Cc1ccc(CO)cc1>ClCCl>CC(C)=Cc1ccc(CBr)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d817accfc9194d7d8c056a712cc00b72 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(Br)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.OB(O)c1ccc(F)cc1>>CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(-c3ccc(F)cc3)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | BrC1=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.FC1=CC=C(C=C1)B(O)O.[F-].[Cs+]>>FC1=CC=C(C=C1)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 | Br[c:20]1[cH:19][cH:18][c:17]([CH2:16][c:15]2[c:10]([O:9][C@@H:8]3[O:7][C@H:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])[C@@H:40]([O:41][C:42]([CH3:43])=[O:44])[C@H:35]([O:36][C:37]([CH3:38])=[O:39])[C@H:30]3[O:31][C:32]([CH3:33])=[O:34])[n:11][nH:12][c:13]2[CH3:14])[cH:29][cH:28]1.OB(O)[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:2... | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(Br)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.OB(O)c1ccc(F)cc1 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(-c3ccc(F)cc3)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC.C(C)O | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc(Cc3c[nH]nc3O[C@H]3CCCCO3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 60.1 | [{"value": 60.1, "product": "FC1=CC=C(C=C1)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", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 18 | HOUR | A mixture of 4-[(4-bromophenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.099 g), 4-fluorophenylboronic acid (0.046 g), cesium fluoride (0.050 g) and tetrakis(triphenylphosphine)palladium(0) (0.0038 g) in 1,2-dimethoxyethane (1.3 mL), ethanol (0.3 mL) and water (0.3 mL) was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | C1CCOCC1.c1cn[nH]c1.c1ccccc1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC.C(C)O | 85 | 18 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(Br)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O.OB(O)c1ccc(F)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC.C(C)O>CC(=O)OC[C@H]1O[C@@H](O... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-97bf7a716be548b498b33e3b8c7e9ac9 | BrC1CCC1.O=Cc1ccc(O)cc1>>O=Cc1ccc(OC2CCC2)cc1 | [OH-].[Na+].OC1=CC=C(C=O)C=C1.C([O-])([O-])=O.[Cs+].[Cs+].C1(CCC1)Br>>C1(CCC1)OC1=CC=C(C=O)C=C1 | Br[CH:8]1[CH2:9][CH2:10][CH2:11]1.[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:12][cH:13]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]2[CH2:9][CH2:10][CH2:11]2)[cH:12][cH:13]1 | BrC1CCC1.O=Cc1ccc(O)cc1 | O=Cc1ccc(OC2CCC2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 6d96532a86b84488fc6bd0e5287d56cd1fadd66f51758349138c69702e9daf1b | cf768afb66ed5041aefdce1fa6d1e40995a1ab7c4b4a4ca47544fe49ee1e629f | c1ccc(OC2CCC2)cc1 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-1):[c:8] | 75.1 | [{"value": 75.1, "product": "C1(CCC1)OC1=CC=C(C=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 8 | HOUR | To a suspension of 4-hydroxybenzaldehyde (0.12 g) and cesium carbonate (0.49 g) in N,N-dimethylformamide (2 mL) was added cyclobutyl bromide (0.15 g), and the mixture was stirred at 65° C. overnight. To the reaction mixture was added 1 mol/L aqueous sodium hydroxide solution, and the mixture was extracted with diethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aromatic alcohol | Ether | C1CCC1 | C1CCC1 | c1ccccc1.C1CCC1 | HBr | CN(C=O)C | 65 | 8 | BrC1CCC1.O=Cc1ccc(O)cc1>CN(C=O)C>O=Cc1ccc(OC2CCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5f4ff8e070b54cb8ac8ee5860bef04f3 | O=Cc1ccc(OC2CCC2)cc1>>OCc1ccc(OC2CCC2)cc1 | Cl.C1(CCC1)OC1=CC=C(C=O)C=C1.[BH4-].[Na+]>>C1(CCC1)OC1=CC=C(CO)C=C1 | [O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]2[CH2:9][CH2:10][CH2:11]2)[cH:12][cH:13]1>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]2[CH2:9][CH2:10][CH2:11]2)[cH:12][cH:13]1 | O=Cc1ccc(OC2CCC2)cc1 | OCc1ccc(OC2CCC2)cc1 | null | null | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccc(OC2CCC2)cc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 91.3 | [{"value": 91.3, "product": "C1(CCC1)OC1=CC=C(CO)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a suspension of 4-hydroxybenzaldehyde (0.12 g) and cesium carbonate (0.49 g) in N,N-dimethylformamide (2 mL) was added cyclobutyl bromide (0.15 g), and the mixture was stirred at 65° C. overnight. To the reaction mixture was added 1 mol/L aqueous sodium hydroxide solution, and the mixture was extracted with diethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1.C1CCC1 | null | CO | null | 8 | O=Cc1ccc(OC2CCC2)cc1>CO>OCc1ccc(OC2CCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e4b9bbe846834bb582b1056ba6ea5d4b | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(-c3ccc(OCc4ccccc4)cc3)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O>>CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(-c3ccc(O)cc3)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | C(C1=CC=CC=C1)OC1=CC=C(C=C1)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>>OC1=CC=C(C=C1)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 | c1ccc(C[O:25][c:24]2[cH:23][cH:22][c:21](-[c:20]3[cH:19][cH:18][c:17]([CH2:16][c:15]4[c:10]([O:9][C@@H:8]5[O:7][C@H:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])[C@@H:40]([O:41][C:42]([CH3:43])=[O:44])[C@H:35]([O:36][C:37]([CH3:38])=[O:39])[C@H:30]5[O:31][C:32]([CH3:33])=[O:34])[n:11][nH:12][c:13]4[CH3:14])[cH:29][cH:28]3)[cH:2... | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(-c3ccc(OCc4ccccc4)cc3)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(-c3ccc(O)cc3)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | null | [C].[Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2ccc(Cc3c[nH]nc3O[C@H]3CCCCO3)cc2)cc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | 58.2 | [{"value": 58.2, "product": "OC1=CC=C(C=C1)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", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 11 | HOUR | To a solution of 4-({4-[4-(benzyloxy)phenyl]phenyl}methyl)-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.14 g) in methanol (3 mL) was added 10% palladium-carbon powder (0.030 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 11 hours. Insoluble materials were... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | C1CCOCC1.c1cn[nH]c1.c1ccccc1.c1ccccc1 | Other | [C].[Pd].CO | null | 11 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(-c3ccc(OCc4ccccc4)cc3)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O>[C].[Pd].CO>CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(-c3ccc(O)cc3)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6744837d271542169edc181f1b3dfcd3 | Cc1ccc(-c2ccccn2)cc1.O=C1CCC(=O)N1Cl>>ClCc1ccc(-c2ccccn2)cc1 | C1(=CC=C(C=C1)C1=NC=CC=C1)C.ClN1C(CCC1=O)=O>>N1=C(C=CC=C1)C1=CC=C(CCl)C=C1 | [CH3:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][n:12]2)[cH:13][cH:14]1.O=C1CCC(=O)N1[Cl:1]>>[Cl:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][n:12]2)[cH:13][cH:14]1 | Cc1ccc(-c2ccccn2)cc1.O=C1CCC(=O)N1Cl | ClCc1ccc(-c2ccccn2)cc1 | null | CC(C)(C#N)N=NC(C)(C)C#N | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Chlorination | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc(-c2ccccn2)cc1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 53.8 | [{"value": 53.8, "product": "N1=C(C=CC=C1)C1=CC=C(CCl)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-(p-tolyl)pyridine (1.7 g) and N-chlorosuccinimide (1.5 g) in carbon tetrachloride (30 mL) was added α,α-azobisisobutyronitrile (0.033 g), and the mixture was heated under reflux for 5 hours. Insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1.c1ccncc1 | HO- | CC(C)(C#N)N=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl | null | null | Cc1ccc(-c2ccccn2)cc1.O=C1CCC(=O)N1Cl>CC(C)(C#N)N=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl>ClCc1ccc(-c2ccccn2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-20c040d52e9041069b9315065b0b9dc3 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(C=C3CC3)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(C=C2CC2)cc1 | 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=C1CC1.C[O-].[Na+]>>[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NNC(=C1CC1=CC=C(C=C1)C=C1CC1)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]([CH:24]=[C:25]3[CH2:26][CH2:27]3)[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(C=C3CC3)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(C=C2CC2)cc1 | null | null | CO | Reduction | OtherReaction | f25a9a23a5ab89548ff4c6a5183e7d00920a9005d871a82164b8da27dcb3ee4f | 613f6029949a010495656f96609cb4885878fc82e324c8aa3a03bf565e6d5cf2 | C(=C1CC1)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] | 99.2 | [{"value": 99.2, "product": "[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NNC(=C1CC1=CC=C(C=C1)C=C1CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A solution of 5-methyl-4-{[4-(cyclopropylidenemethyl)phenyl]methyl}-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.010 g) in methanol (2 mL) was added sodium methoxide (28% methanol solution, 0.0020 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrat... | 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.C1CC1 | HO- | CO | null | 0.5 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(C=C3CC3)cc2)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O>CO>Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(C=C2CC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-712420777a354dadae1bb00c8c7fe75a | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(C3CC3)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(C2CC2)cc1 | 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)C1CC1.[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)C1CC1)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]([CH:24]3[CH2:25][CH2:26]3)[cH:27][cH:28]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]([OH:1... | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(C3CC3)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(C2CC2)cc1 | null | null | C(C)O | Reduction | OtherReaction | f25a9a23a5ab89548ff4c6a5183e7d00920a9005d871a82164b8da27dcb3ee4f | 613f6029949a010495656f96609cb4885878fc82e324c8aa3a03bf565e6d5cf2 | c1cc(C2CC2)ccc1Cc1c[nH]nc1O[C@H]1CCCCO1 | 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] | 88.9 | [{"value": 88.9, "product": "[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NNC(=C1CC1=CC=C(C=C1)C1CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 5-methyl-4-[(4-cyclopropylphenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.14 g) in ethanol (8.4 mL) was added 2 mol/L aqueous sodium hydroxide solution (0.63 mL), and the mixture was stirred at room temperature for 30 minutes. The solvent was removed under reduced pressur... | 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.C1CC1 | HO- | C(C)O | null | 0.5 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2ccc(C3CC3)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(C2CC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f73b9914b2544aef8093298d9c350683 | CC(C)I.Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(C2CC2)cc1>>Cc1c(Cc2ccc(C3CC3)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C(C)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)C1CC1)C.C([O-])([O-])=O.[Cs+].[Cs+].IC(C)C>>[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NN(C(=C1CC1=CC=C(C=C1)C1CC1)C)C(C)C | I[CH:29]([CH3:30])[CH3:31].[CH3:1][c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[cH:12][cH:13]2)[c:14]([O:15][C@@H:16]2[O:17][C@H:18]([CH2:19][OH:20])[C@@H:21]([OH:22])[C@H:23]([OH:24])[C@H:25]2[OH:26])[n:27][nH:28]1>>[CH3:1][c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[cH:1... | CC(C)I.Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(C2CC2)cc1 | Cc1c(Cc2ccc(C3CC3)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C(C)C | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 16e7264339c5da2b038fe36dfca9cfcc21c80f0292d644875f157fe8da0791e0 | 3456c966f3f7e7d410f206842ab08ae4d1cfab4368ca2a0de7a6ad251462e6f4 | c1cc(C2CC2)ccc1Cc1c[nH]nc1O[C@H]1CCCCO1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[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;H3:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[n;H0;D3;+0:9]:1-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3] | null | [] | null | null | 35 | MINUTE | To a suspension of 3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole (56 mg) and cesium carbonate (23 mg) in N,N-dimethylformamide (1.5 mL) was added 2-iodopropane (0.043 mL) at 80° C., and the mixture was stirred for 35 minutes. To the reaction mixture was added water, and the mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | null | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.C1CC1.C1CCOCC1 | HI | CN(C=O)C | null | 0.583333 | CC(C)I.Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(C2CC2)cc1>CN(C=O)C>Cc1c(Cc2ccc(C3CC3)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-26f326e36a904d5e9f2369e5f379ac90 | Cc1[nH][nH]c(=O)c1Cc1ccc(-c2ccccn2)cc1>>Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(-c2ccccn2)cc1 | CC1=C(C(NN1)=O)CC1=CC=C(C=C1)C1=NC=CC=C1.CC1=C(C(=NN1)O[C@H]1[C@](O)([C@@](O)([C@](O)([C@H](O1)C(O)C(C)=O)C(C)=O)C(C)=O)C(C)=O)CC1=CC=C(C=C1)C1=NC=CC=C1>>CC1=C(C(=NN1)O[C@H]1[C@](O)([C@@](O)([C@](O)([C@H](O1)C(O)C(C)=O)C(C)=O)C(C)=O)C(C)=O)CC1=CC=C(C=C1)C1=NC=CC=C1.[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NNC(=... | [CH3:44][c:45]1[nH:46][nH:47][c:48](=[O:49])[c:61]1[CH2:62][c:63]1[cH:64][cH:65][c:66](-[c:67]2[cH:68][cH:69][cH:70][cH:71][n:72]2)[cH:73][cH:74]1>>[CH3:44][c:45]1[nH:46][n:47][c:48]([O:49][C@@H:50]2[O:51][C@H:52]([CH2:53][OH:54])[C@@H:55]([OH:56])[C@H:57]([OH:58])[C@H:59]2[OH:60])[c:61]1[CH2:62][c:63]1[cH:64][cH:65][c... | Cc1[nH][nH]c(=O)c1Cc1ccc(-c2ccccn2)cc1 | Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(-c2ccccn2)cc1 | null | null | null | Functional Group Interconversion | OtherReaction | ead1fc6f6adf9c6d299f2cfdd5a28b72dce9daf92747912a06341759e2e7b8cd | 6f24b6011ab4070dd247a50f72b747bca7d9d29ae512b8f5758535ae9ced16bd | c1ccc(-c2ccc(Cc3c[nH]nc3O[C@H]3CCCCO3)cc2)nc1 | [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-(pyridin-2-yl)phenyl]methyl}-3-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-1H-pyrazole was prepared in a similar manner to that described in Example 4 using 5-methyl-4-{[4-(pyridin-2-yl)phenyl]methyl}-1,2-dihydro-3H-pyrazol-3-one instead of 5-methyl-4-[(4-cyclopropylphenyl)methyl]-1,2-dihydro-3H-pyrazol-... | 10.6084/m9.figshare.5104873.v1 | null | null | Ether.Ether.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | c1cn[nH]c1 | c1cn[nH]c1.C1CCOCC1 | c1cn[nH]c1.C1CCOCC1.c1ccccc1.c1ccncc1 | Other | null | null | null | Cc1[nH][nH]c(=O)c1Cc1ccc(-c2ccccn2)cc1>>Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(-c2ccccn2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e1891c54274e463798b044aadeb68576 | CC(=O)OCCBr.Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(C2CC2)cc1>>Cc1c(Cc2ccc(C3CC3)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1CCO | [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)C1CC1)C.C([O-])([O-])=O.[Cs+].[Cs+].C(C)(=O)OCCBr>>[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NN(C(=C1CC1=CC=C(C=C1)C1CC1)C)CCO | CC(=O)[O:31][CH2:30][CH2:29]Br.[CH3:1][c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[cH:12][cH:13]2)[c:14]([O:15][C@@H:16]2[O:17][C@H:18]([CH2:19][OH:20])[C@@H:21]([OH:22])[C@H:23]([OH:24])[C@H:25]2[OH:26])[n:27][nH:28]1>>[CH3:1][c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[... | CC(=O)OCCBr.Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(C2CC2)cc1 | Cc1c(Cc2ccc(C3CC3)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1CCO | null | null | CO.O.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | d852c722c2aca2b7d389659753689a45a4758ac8a419d359b535bfc85cb51b90 | 54abde2d478ff296b6bbfd081f08f62192a65526240f7099e8b16537b3165ae6 | c1cc(C2CC2)ccc1Cc1c[nH]nc1O[C@H]1CCCCO1 | Br-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-C(-C)=O.[C;D1;H3:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[C;D1;H3:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[n;H0;D3;+0:9]:1-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3] | null | [] | null | null | 2 | HOUR | To a suspension of 3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole (33 mg) and cesium carbonate (138 mg) in N,N-dimethylformamide (1 mL) was added 2-bromoethyl acetate (0.035 mL) at 40° C., and the mixture was stirred for 2 hours. To the reaction mixture was added water, and the mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Primary alcohol | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.C1CC1.C1CCOCC1 | HBr | CO.O.CN(C=O)C | null | 2 | CC(=O)OCCBr.Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(C2CC2)cc1>CO.O.CN(C=O)C>Cc1c(Cc2ccc(C3CC3)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1CCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-109fe8804b6a4af0845004d8cdb6b4e7 | BrCCOCc1ccccc1.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)nn(CCOCc3ccccc3)c2C)cc1 | [OH-].[Na+].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([O-])([O-])=O.[Cs+].[Cs+].C(C1=CC=CC=C1)OCCBr>>C(C1=CC=CC=C1)OCCN1N=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 | Br[CH2:24][CH2:25][O:26][CH2:27][c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1.CC(=O)[O:15][CH2:14][C@H:13]1[O:12][C@@H:11]([O:10][c:9]2[c:8]([CH2:7][c:6]3[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:37][cH:36]3)[c:34]([CH3:35])[nH:23][n:22]2)[C@H:20]([O:21]C(C)=O)[C@@H:18]([O:19]C(C)=O)[C@@H:16]1[O:17]C(C)=O>>[CH3:1][CH2:2][c:3]... | BrCCOCc1ccccc1.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)nn(CCOCc3ccccc3)c2C)cc1 | null | null | CO.O.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 6ee0687f8babb1e9e5cf5916e44ac5b5c459bb6a896b3332ada71047bcded01e | d801f850e0a060636a41be97e2f9380e4486de67ba2f3b00fe109c16997b93ef | c1ccc(COCCn2cc(Cc3ccccc3)c(O[C@H]3CCCCO3)n2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].C-C(=O)-[O;H0;D2;+0:4]-[C:5]-[C:6]1-[#8:7]-[C:8]-[C:9](-[O;H0;D2;+0:10]-C(-C)=O)-[C:11](-[O;H0;D2;+0:12]-C(-C)=O)-[C:13]-1-[O;H0;D2;+0:14]-C(-C)=O.[C;D1;H3:15]-[c:16]1:[c:17]:[c:18]:[#7;a:19]:[nH;D2;+0:20]:1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:20]1:[#7;a:19]:[c:18]:[c:17]:[c:16]:1-[C;D... | null | [] | 80 | CELSIUS | 30 | MINUTE | To a suspension of 4-[(4-ethylphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.030 g) and cesium carbonate (0.091 g) in acetonitrile (0.4 mL) was added benzyl(2-bromoethyl)ether (0.035 mL), and the mixture was stirred at 80° C. for 30 minutes. After cooling to room temperature, th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester.Ester.Ester | Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | c1cn[nH]c1 | c1cn[nH]c1 | c1ccccc1.C1CCOCC1.c1cn[nH]c1.c1ccccc1 | HBr | CO.O.C(C)#N | 80 | 0.5 | BrCCOCc1ccccc1.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>CO.O.C(C)#N>CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CCOCc3ccccc3)c2C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8b516180d4e44f6ab2a17607b71443c4 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2sccc2C)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O>>CSc1ccc(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[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O)CC=1SC=CC1C.C[O-].[Na+].C(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)SC)C | CC(=O)[O:15][CH2:14][C@H:13]1[O:12][C@@H:11]([O:10][c:9]2[c:8]([CH2:7][c:6]3[s:2][cH:3][cH:4][c:5]3[CH3:26])[c:24]([CH3:25])[nH:23][n:22]2)[C@H:20]([O:21]C(C)=O)[C@@H:18]([O:19]C(C)=O)[C@@H:16]1[O:17]C(C)=O>>[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][OH:15])[C@@H:16](... | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2sccc2C)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O | CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1 | null | null | null | Miscellaneous | OtherReaction | 0cdfed43039c68caaeff6b35e038f2ba97c89e0158bda5e1b4b95f9551247d29 | 1c2f9a866c22d324ca04dd42d041706cd3480ef8d7d753c19b41d48590c4c482 | 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.[CH3;D1;+0:12]-[c;H0;D3;+0:13]1:[c:14]:[cH;D2;+0:15]:[s;H0;D2;+0:16]:[c;H0;D3;+0:17]:1-[C:18]-[c:19]1:[c:20]:[#7;a:21]:[#7;a:22]:[c:23]:1>>[C;D1;H3:24]-[S;H0;D2;+0:16]-[c;H0;D3... | null | [] | null | null | 1 | HOUR | To a solution of 5-methyl-4-[(methylthiophenyl)methyl]-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.42 g) in ethanol (5 mL) was added sodium methoxide (28% methanol solution, 0.042 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pre... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester.Ester | Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Monosulfide | c1ccsc1 | c1ccccc1 | c1ccccc1.C1CCOCC1.c1cn[nH]c1 | HO- | null | null | 1 | CC(=O)OC[C@H]1O[C@@H](Oc2n[nH]c(C)c2Cc2sccc2C)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O>>CSc1ccc(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-565d90381b814599892f25d706657501 | 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}] | 65 | CELSIUS | 8 | HOUR | To a suspension of 4-[(4-isopropoxyphenyl)methyl]-5-methyl-1,2-dihydro-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 at 65° C. overnight under light shielding. The reaction mixture was purified b... | 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 | 65 | 8 | 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-65c85569dca248bba77632215a4e4b48 | 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-061bca7ca0d24355a6d61c73b9464cfc | CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CCOCc3ccccc3)c2C)cc1>>Cc1ccnn1CCO | C(C1=CC=CC=C1)OCCN1N=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>>OCCN1N=CC=C1C | CCc1ccc(C[c:3]2[c:2]([CH3:1])[n:6]([CH2:7][CH2:8][O:9]Cc3ccccc3)[n:5][c:4]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1>>[CH3:1][c:2]1[cH:3][cH:4][n:5][n:6]1[CH2:7][CH2:8][OH:9] | CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CCOCc3ccccc3)c2C)cc1 | Cc1ccnn1CCO | null | [C].[Pd] | C(C)O | Reduction | OtherReaction | 360868ba954e0c04c8c98a7bc724315b8b64f892bc0d297f40f854fdbe539055 | f2e1056b76894f3ffea8a99e38b24ab137cec9a13a66d2264741f4b40927f61c | c1cn[nH]c1 | C-C-c1:c:c:c(-C-[c;H0;D3;+0:1]2:[c:2](-[C;D1;H3:3]):[#7;a:4](-[C:5]-[C:6]-[O;H0;D2;+0:7]-C-c3:c:c:c:c:c:3):[#7;a:8]:[c;H0;D3;+0:9]:2-O-[C@H]2-O-[C@H](-C-O)-[C@@H](-O)-[C@H](-O)-[C@@H]-2-O):c:c:1>>[C;D1;H3:3]-[c:2]1:[cH;D2;+0:1]:[cH;D2;+0:9]:[#7;a:8]:[#7;a:4]:1-[C:5]-[C:6]-[OH;D1;+0:7] | 372.5 | [{"value": 372.5, "product": "OCCN1N=CC=C1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 1-(2-benzyloxyethyl)-4-[(4-ethylphenyl)methyl]-3-(β-D-glucopyranosyloxy)-5-methyl-1H-pyrazole (0.012 g) in ethanol (2 mL) was added a catalytic amount of 10% palladium-carbon powder, and the mixture was stirred at room temperature under a hydrogen atmosphere for 30 minutes. Insoluble materials were rem... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | Primary alcohol | c1ccccc1.c1cn[nH]c1.c1ccccc1.C1CCOCC1 | c1cc[nH]n1 | c1cc[nH]n1 | HO- | [C].[Pd].C(C)O | null | 0.5 | CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CCOCc3ccccc3)c2C)cc1>[C].[Pd].C(C)O>Cc1ccnn1CCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9a0224bc18ff4dde8591bc36f4b1149a | CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1.OCCCBr>>CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CCCO)c2C)cc1 | O.[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NNC(=C1CC1=CC=C(C=C1)SC)C.C([O-])([O-])=O.[Cs+].[Cs+].BrCCCO>>[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NN(C(=C1CC1=CC=C(C=C1)SC)C)CCCO | [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][OH:15])[C@@H:16]([OH:17])[C@H:18]([OH:19])[C@H:20]3[OH:21])[n:22][nH:23][c:28]2[CH3:29])[cH:30][cH:31]1.Br[CH2:24][CH2:25][CH2:26][OH:27]>>[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](... | CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1.OCCCBr | CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CCCO)c2C)cc1 | 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 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[nH;D2;+0:9]:1>>[C: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 | [] | 40 | CELSIUS | 8 | HOUR | To a suspension of 3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole (0.020 g) and cesium carbonate (0.11 g) in N,N-dimethylformamide (0.5 mL) was added 3-bromopropanol (0.022 mL), and the mixture was stirred at 40° C. overnight. To the reaction mixture was added water, and the mixture was p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cn[nH]c1 | c1cn[nH]c1 | c1ccccc1.C1CCOCC1.c1cn[nH]c1 | HBr | CN(C=O)C | 40 | 8 | CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1.OCCCBr>CN(C=O)C>CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CCCO)c2C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aa90f8b214a24555af3b5a9a4cc0ed66 | C=CCI.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=CCn1nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(Cc2ccc(CC)cc2)c1C | [OH-].[Na+].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([O-])([O-])=O.[Cs+].[Cs+].C(C=C)I>>C(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[CH2:3][CH:2]=[CH2:1].CC(=O)[O:12][CH2:11][C@H:10]1[O:9][C@@H:8]([O:7][c:6]2[n:5][nH:4][c:29]([CH3:30])[c:19]2[CH2:20][c:21]2[cH:22][cH:23][c:24]([CH2:25][CH3:26])[cH:27][cH:28]2)[C@H:17]([O:18]C(C)=O)[C@@H:15]([O:16]C(C)=O)[C@@H:13]1[O:14]C(C)=O>>[CH2:1]=[CH:2][CH2:3][n:4]1[n:5][c:6]([O:7][C@@H:8]2[O:9][C@H:10]([CH2:... | C=CCI.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=CCn1nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(Cc2ccc(CC)cc2)c1C | null | null | CO.O.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 86f197887924543584440aec8dd5852a59f1ca6af42669d4366a4869dc0f7b92 | f126eb1e2efac33fff492856e1c02e35fd2d9ad264b3d1e1e904df355a9609c4 | 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.[C;D1;H3:12]-[c:13]1:[c:14]:[c:15]:[#7;a:16]:[nH;D2;+0:17]:1.I-[CH2;D2;+0:18]-[C:19]=[C;D1;H2:20]>>[C;D1;H2:20]=[C:19]-[CH2;D2;+0:18]-[n;H0;D3;+0:17]1:[#7;a:16]:[c:15]:[c:14]:[... | null | [] | null | null | 1 | HOUR | To a suspension of 4-[(4-ethylphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.030 g) and cesium carbonate (0.036 g) in acetonitrile (0.4 mL) was added allyl iodide (0.010 mL), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture were added methanol ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester.Ester.Ester.Allyl | Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol.Allyl | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.C1CCOCC1.c1ccccc1 | HI | CO.O.C(C)#N | null | 1 | C=CCI.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>CO.O.C(C)#N>C=CCn1nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c(Cc2ccc(CC)cc2)c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-18c5dd7d2c2244d79595acf160ae3565 | BrCC1CC1.CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1>>CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CC3CC3)c2C)cc1 | [I-].[Na+].[C@@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)OC1=NNC(=C1CC1=CC=C(C=C1)SC)C.C([O-])([O-])=O.[Cs+].[Cs+].BrCC1CC1>>C1(CC1)CN1N=C(C(=C1C)CC1=CC=C(C=C1)SC)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO | Br[CH2:24][CH:25]1[CH2:26][CH2:27]1.[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][OH:15])[C@@H:16]([OH:17])[C@H:18]([OH:19])[C@H:20]3[OH:21])[n:22][nH:23][c:28]2[CH3:29])[cH:30][cH:31]1>>[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... | BrCC1CC1.CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1 | CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CC3CC3)c2C)cc1 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 31849359320dc3760d1a762ce95f120a544970fcb32b476aacf584ef81779a29 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cc2cn(CC3CC3)nc2O[C@H]2CCCCO2)cc1 | Br-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[nH;D2;+0:10]:1>>[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[n;H0;D3;+0:10]:1-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1 | null | [] | null | null | null | null | To a solution of 3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole (0.081 g) in N,N-dimethylformamide (1 mL) were added cesium carbonate (0.40 g), bromomethylcyclopropane (0.099 mL) and a catalytic amount of sodium iodide, and the mixture was stirred at room temperature for 7 days. Water was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cn[nH]c1 | c1cn[nH]c1 | c1ccccc1.C1CCOCC1.c1cn[nH]c1.C1CC1 | HBr | O.CN(C=O)C | null | null | BrCC1CC1.CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1>O.CN(C=O)C>CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CC3CC3)c2C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b269f573691d4ca6aca44037f3491647 | BrCCCOCc1ccccc1.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)nn(CCCO)c2C)cc1 | [OH-].[Na+].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([O-])([O-])=O.[Cs+].[Cs+].C(C1=CC=CC=C1)OCCCBr>>C(C)C1=CC=C(C=C1)CC=1C(=NN(C1C)CCCO)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO | Br[CH2:24][CH2:25][CH2:26][O:27]Cc1ccccc1.CC(=O)[O:15][CH2:14][C@H:13]1[O:12][C@@H:11]([O:10][c:9]2[c:8]([CH2:7][c:6]3[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:31][cH:30]3)[c:28]([CH3:29])[nH:23][n:22]2)[C@H:20]([O:21]C(C)=O)[C@@H:18]([O:19]C(C)=O)[C@@H:16]1[O:17]C(C)=O>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][c:8]2[c... | BrCCCOCc1ccccc1.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)nn(CCCO)c2C)cc1 | null | null | CO.O.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 9ab42c90d847e96b9b80d52bf0ff6ac70490bebeda01adde8871f99f9e0d96de | e25864d4e27a8101363e96bf37d311b351fc70dd354922080edad2faae228b3e | c1ccc(Cc2c[nH]nc2O[C@H]2CCCCO2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1.C-C(=O)-[O;H0;D2;+0:5]-[C:6]-[C:7]1-[#8:8]-[C:9]-[C:10](-[O;H0;D2;+0:11]-C(-C)=O)-[C:12](-[O;H0;D2;+0:13]-C(-C)=O)-[C:14]-1-[O;H0;D2;+0:15]-C(-C)=O.[C;D1;H3:16]-[c:17]1:[c:18]:[c:19]:[#7;a:20]:[nH;D2;+0:21]:1>>[C;D1;H3:16]-[c:17]1:[c:18]:[c:19]:[#7;a:20]:[n;H... | null | [] | 80 | CELSIUS | 30 | MINUTE | To a suspension of 4-[(4-ethylphenyl)methyl]-5-methyl-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.030 g) and cesium carbonate (0.091 g) in acetonitrile (0.4 mL) was added benzyl(3-bromopropyl)ether (0.039 mL), and the mixture was stirred at 80° C. for 30 minutes. To the reaction mixture were added m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester.Ester.Ester.Ether | Primary alcohol.Primary alcohol.Secondary alcohol.Secondary alcohol.Secondary alcohol | c1ccccc1.c1cn[nH]c1 | c1cn[nH]c1 | c1ccccc1.C1CCOCC1.c1cn[nH]c1 | HBr | CO.O.C(C)#N | 80 | 0.5 | BrCCCOCc1ccccc1.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>CO.O.C(C)#N>CCc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CCCO)c2C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0f63970ca7eb460d85e9a8fe0683d4ce | BrCC1CC1.Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(OC(C)C)cc1>>Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1CC1CC1 | 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.[I-].[Na+].BrCC1CC1>>C1(CC1)CN1N=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 | Br[CH2:30][CH:31]1[CH2:32][CH2:33]1.[CH3:1][c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][c:8]([O:9][CH:10]([CH3:11])[CH3:12])[cH:13][cH:14]2)[c:15]([O:16][C@@H:17]2[O:18][C@H:19]([CH2:20][OH:21])[C@@H:22]([OH:23])[C@H:24]([OH:25])[C@H:26]2[OH:27])[n:28][nH:29]1>>[CH3:1][c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][c:8]([O:9][CH:10]([C... | BrCC1CC1.Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(OC(C)C)cc1 | Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1CC1CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 31849359320dc3760d1a762ce95f120a544970fcb32b476aacf584ef81779a29 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(Cc2cn(CC3CC3)nc2O[C@H]2CCCCO2)cc1 | Br-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1.[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[nH;D2;+0:10]:1>>[C;D1;H3:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[n;H0;D3;+0:10]:1-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-1 | 60 | [{"value": 60.0, "product": "C1(CC1)CN1N=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", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a suspension of 3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole (0.050 g) cesium carbonate (0.20 g) and a catalytic amount of sodium iodide in N,N-dimethylformamide (1 mL) was added bromomethylcyclopropane (0.050 g) at 50° C., and the mixture was stirred for 3 days. Water was added to t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.C1CCOCC1.C1CC1 | HBr | CN(C=O)C | null | 72 | BrCC1CC1.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>Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1CC1CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c3d1338347874e4b9770a415431dc81b | BrC1CCCC1.Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(OC(C)C)cc1>>Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C1CCCC1 | 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+].C1(CCCC1)Br>>C1(CCCC1)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 | Br[CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34]1.[CH3:1][c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][c:8]([O:9][CH:10]([CH3:11])[CH3:12])[cH:13][cH:14]2)[c:15]([O:16][C@@H:17]2[O:18][C@H:19]([CH2:20][OH:21])[C@@H:22]([OH:23])[C@H:24]([OH:25])[C@H:26]2[OH:27])[n:28][nH:29]1>>[CH3:1][c:2]1[c:3]([CH2:4][c:5]2[cH:6][cH:7][c:8]([O:9][C... | BrC1CCCC1.Cc1[nH]nc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c1Cc1ccc(OC(C)C)cc1 | Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C1CCCC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b6d603a26a93a1070dbd9cb4e26fba0f00d31dc341b43ea3961a58bc9ca18137 | 3456c966f3f7e7d410f206842ab08ae4d1cfab4368ca2a0de7a6ad251462e6f4 | c1ccc(Cc2cn(C3CCCC3)nc2O[C@H]2CCCCO2)cc1 | Br-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1.[C;D1;H3:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[nH;D2;+0:11]:1>>[C;D1;H3:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[n;H0;D3;+0:11]:1-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1 | 58.3 | [{"value": 58.3, "product": "C1(CCCC1)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", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a suspension of 3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole (0.050 g) and cesium carbonate (0.20 g) in N,N-dimethylformamide (1 mL) was added cyclopentyl bromide (0.055 g) at 80° C., and the mixture was stirred for 30 minutes. After cooling to room temperature, water was added to th... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide | null | C1CCCC1.c1cn[nH]c1 | c1cn[nH]c1.C1CCCC1 | c1cn[nH]c1.c1ccccc1.C1CCOCC1.C1CCCC1 | HBr | CN(C=O)C | null | 0.5 | BrC1CCCC1.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>Cc1c(Cc2ccc(OC(C)C)cc2)c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)nn1C1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2d65b92df53145f896e32cc79fe50f43 | 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)nn1CC1CC1>>CCC(=O)OC[C@H]1O[C@@H](Oc2nn(CC3CC3)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.C1(CC1)CN1N=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.C(CC)(=O)Cl>>C1(CC1)CN1N=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(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]([CH2:14][CH:15]3[CH2:16][CH2:17]3)[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][C:3](=[O:4])[O:5][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)nn1CC1CC1 | CCC(=O)OC[C@H]1O[C@@H](Oc2nn(CC3CC3)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(Cc2cn(CC3CC3)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] | 405.5 | [{"value": 405.5, "product": "C1(CC1)CN1N=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(CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 1-(cyclopropylmethyl)-3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole (0.40 g) in 2,4,6-trimethylpyridine (1.5 mL) was added propionyl chloride (0.0088 g) at 0° C., and the mixture was stirred for 3 hours. Citric acid monohydrate (3.3 g) and water were added to the reactio... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | C1CCOCC1.c1cn[nH]c1.C1CC1.c1ccccc1 | HCl | CC1=NC(=CC(=C1)C)C | null | 3 | 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)nn1CC1CC1>CC1=NC(=CC(=C1)C)C>CCC(=O)OC[C@H]1O[C@@H](Oc2nn(CC3CC3)c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a263acd080c74398b09f94a2fc949eda | 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)nn1CC1CC1>>CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(CC3CC3)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.C1(CC1)CN1N=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>>C1(CC1)CN1N=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]([CH2:15][CH:16]3[CH2:17][CH2:18]3)[c:19]([CH3:20])[c:21]2[CH2:22][c:23]2[cH:24][cH:25][c:26]([O:27][CH:28]([CH3:29])[CH3:30])[cH:31][cH:32]2)[C@H:33]([OH:34])[C@@H:35]([OH:36])[C@@H:37]1[OH:38]>>[CH3:1][CH2:2][O:3][C:4](=[O... | 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)nn1CC1CC1 | CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(CC3CC3)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(Cc2cn(CC3CC3)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] | 74.4 | [{"value": 74.4, "product": "C1(CC1)CN1N=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", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 1-(cyclopropylmethyl)-3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-1H-pyrazole (0.050 g) in 2,4,6-trimethylpyridine (1 mL) was added ethyl chloroformate (0.035 g), and the mixture was stirred at room temperature overnight. Citric acid monohydrate (3.3 g) and water were added to the... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary alcohol | Carbonic Ester | null | null | C1CCOCC1.c1cn[nH]c1.C1CC1.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)nn1CC1CC1>CC1=NC(=CC(=C1)C)C>CCOC(=O)OC[C@H]1O[C@@H](Oc2nn(CC3CC3)c(C)c2Cc2ccc(OC(C)C)cc2)[C@H](O)[C@@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c7f6d570e3cd42f6a92e57cb911288ae | CC[C@@H](C(N)=O)N1CCC(COS(C)(=O)=O)CC1=O.[I-]>>CC[C@@H](C(N)=O)N1CCC(CI)CC1=O | [I-].[Na+].CS(=O)(=O)OCC1CC(N(CC1)[C@@H](CC)C(=O)N)=O.[I-].[Na+]>>ICC1CC(N(CC1)[C@H](C(=O)N)CC)=O | CS(=O)(=O)O[CH2:11][CH:10]1[CH2:9][CH2:8][N:7]([C@@H:3]([CH2:2][CH3:1])[C:4]([NH2:5])=[O:6])[C:14](=[O:15])[CH2:13]1.[I-:12]>>[CH3:1][CH2:2][C@@H:3]([C:4]([NH2:5])=[O:6])[N:7]1[CH2:8][CH2:9][CH:10]([CH2:11][I:12])[CH2:13][C:14]1=[O:15] | CC[C@@H](C(N)=O)N1CCC(COS(C)(=O)=O)CC1=O.[I-] | CC[C@@H](C(N)=O)N1CCC(CI)CC1=O | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 119410ad0456baafba3b2935b12d3e44977c506a6dd8cacdd3e4fe37abe9db9f | ddf832dd4937bef392b42ed4281006ae20524cc7fc61b350edeb12d7b5bf783f | O=C1CCCCN1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[C:5](=[O;D1;H0:6])-[#7:7].[I-;H0;D0:8]>>[#7:7]-[C:5](=[O;D1;H0:6])-[C:4]-[C:2](-[CH2;D2;+0:1]-[I;H0;D1;+0:8])-[C:3] | 65,636,364 | [{"value": 66.0, "product": "ICC1CC(N(CC1)[C@H](C(=O)N)CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65636364.0, "product": "ICC1CC(N(CC1)[C@H](C(=O)N)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | HOUR | In a 150 ml three necked flask fitted with magnetic stirrer and reflux condenser, under inert atmosphere, 6.88 g (23.5 nmoles) of {1-[(1S)-1-(aminocarbonyl)propyl]-6-oxo-3-piperidinyl}methyl methanesulfonate 24 were dissolved in 86 ml of THF. 3.9 g (25.9 mmoles, 1.1 eq) of sodium iodide were added in one portion and th... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | Primary halide | null | null | C1CC[NH]CC1 | MsOH.HO- | C1CCOC1 | 0 | 5 | CC[C@@H](C(N)=O)N1CCC(COS(C)(=O)=O)CC1=O.[I-]>C1CCOC1>CC[C@@H](C(N)=O)N1CCC(CI)CC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1eef3dbcfb0c48a58fb44f859aa4293d | CCOC(=O)C(Br)CC.O=C1CCC(c2ccccc2)CN1>>CCOC(=O)C(CC)N1CC(c2ccccc2)CCC1=O | BrC(C(=O)OCC)CC.CC(C)([O-])C.[K+].C(C)(=O)OCC.C1(=CC=CC=C1)C1CCC(NC1)=O>>O=C1N(CC(CC1)C1=CC=CC=C1)C(C(=O)OCC)CC | Br[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH3:8].[NH:9]1[CH2:10][CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19][C:20]1=[O:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH3:8])[N:9]1[CH2:10][CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19][C:20]1=[O:21] | CCOC(=O)C(Br)CC.O=C1CCC(c2ccccc2)CN1 | CCOC(=O)C(CC)N1CC(c2ccccc2)CCC1=O | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bd0f600bacc94ea43dea015f98985d948c00d421c78f487c2d3e740688f9c6bb | 29b3e231b1d2708086b87ea5e8bddd4b64f3d7251e67b4cc4f6db43e63a60af6 | O=C1CCC(c2ccccc2)CN1 | Br-[CH;D3;+0:1](-[C:2]-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11](=[O;D1;H0:12])-[C:13]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[CH;D3;+0:1](-[C:2]-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[C:11](=[O;D1;H0:12])-[C:13] | 70.4 | [{"value": 70.4, "product": "O=C1N(CC(CC1)C1=CC=CC=C1)C(C(=O)OCC)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 19.1, "product": "O=C1N(CC(CC1)C1=CC=CC=C1)C(C(=O)OCC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 30 | MINUTE | In a 1 l three necked flask fitted with reflux condenser, magnetic stirrer and dropping funnel under inert atmosphere, 9.8 g (87 mmoles) of potassium t-butoxide were suspended in 600 ml of dry toluene. 11.8 g (67 mmoles) of 5-phenyl-2-piperidinone 25 were added, and the mixture stirred for 30 min. 17 g (87 mmoles) of e... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Secondary amide | Ester.Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | HBr | C1(=CC=CC=C1)C | 70 | 0.5 | CCOC(=O)C(Br)CC.O=C1CCC(c2ccccc2)CN1>C1(=CC=CC=C1)C>CCOC(=O)C(CC)N1CC(c2ccccc2)CCC1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-98c17061ed0941a5ba5bcf3a6530bf66 | CCOC(=O)C1CCC(=O)CC1>>CCOC(=O)C1CCNC(=O)CC1 | CS(=O)(=O)O.O=C1CCC(CC1)C(=O)OCC.C([O-])(O)=O.[Na+].[N-]=[N+]=[N-].[Na+]>>O=C1CCC(CCN1)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][C:10](=[O:11])[CH2:12][CH2:13]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][NH:9][C:10](=[O:11])[CH2:12][CH2:13]1 | CCOC(=O)C1CCC(=O)CC1 | CCOC(=O)C1CCNC(=O)CC1 | null | null | C(Cl)(Cl)Cl | Functional Group Addition | Schmidt ketone amide | bd03f575cc59664fd68bc4dea65aaf5b902271d018d65d5bd3b85398a36f8d70 | 2eb609f54422c0279557c5451dffbcf43fa7dc53a915eee10665042f34f6a171 | O=C1CCCCCN1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[C:5]-[C:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[C:5]-[C:6]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[#7:11]-[CH2;D2;+0:9]-[C:10]-1 | 70 | [{"value": 70.0, "product": "O=C1CCC(CCN1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.0, "product": "O=C1CCC(CCN1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | null | null | In a 250 ml three necked flask fitted with reflux condenser, magnetic stirrer and dropping funnel under inert atmosphere, 5.6 ml (5.98 g, 34 mmoles, 1 eq) of ethyl 4-oxocyclohexanecarboxylate 27 were dissolved in 50 ml of CHCl3. 6.65 g (102 mmole, 3 eq) of sodium azide were added, followed by 22.1 ml (32.8 g, 341 mmole... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary amide | C1CCCCC1 | C1CCCNCC1 | C1CCCNCC1 | Other | C(Cl)(Cl)Cl | 10 | null | CCOC(=O)C1CCC(=O)CC1>C(Cl)(Cl)Cl>CCOC(=O)C1CCNC(=O)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-82f8dd09f130443ab0aefbeeb0485fd7 | CCC(Br)C(=O)OC(C)(C)C.CCOC(=O)C1CCNC(=O)CC1>>CCOC(=O)C1CCC(=O)N(C(CC)C(=O)OC(C)(C)C)CC1 | [H-].[Na+].O=C1CCC(CCN1)C(=O)OCC.BrC(C(=O)OC(C)(C)C)CC>>C(C)(C)(C)OC(=O)C(CC)N1CCC(CCC1=O)C(=O)OCC | Br[CH:12]([CH2:13][CH3:14])[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21].[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][C:9](=[O:10])[NH:11][CH2:22][CH2:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][C:9](=[O:10])[N:11]([CH:12]([CH2:13][CH3:14])[C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20... | CCC(Br)C(=O)OC(C)(C)C.CCOC(=O)C1CCNC(=O)CC1 | CCOC(=O)C1CCC(=O)N(C(CC)C(=O)OC(C)(C)C)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 7e2d047380fda5ccab9522d1ecd6114ed9ac7870607d92d33de993ebbcc7e977 | 29b3e231b1d2708086b87ea5e8bddd4b64f3d7251e67b4cc4f6db43e63a60af6 | O=C1CCCCCN1 | Br-[CH;D3;+0:1](-[C:2]-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10].[C:11]-[C:12]-[NH;D2;+0:13]-[C:14](=[O;D1;H0:15])-[C:16]>>[C:11]-[C:12]-[N;H0;D3;+0:13](-[CH;D3;+0:1](-[C:2]-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[C:14](=[O;D1... | 94.4 | [{"value": 69.0, "product": "C(C)(C)(C)OC(=O)C(CC)N1CCC(CCC1=O)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.4, "product": "C(C)(C)(C)OC(=O)C(CC)N1CCC(CCC1=O)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | In a 150 ml three necked flask fitted with reflux condenser, magnetic stirrer and dropping funnel under inert atmosphere, 5.09 g (27.5 mmoles, 1 eq) of ethyl 7-oxo-4-azepanecarboxylate 28 and 12.27 g (55 mmoles, 2 eq) of tert-butyl 2-bromobutanoate were dissolved in 70 ml of acetonitrile. The temperature was raised to ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Secondary amide | Ester.Tertiary amide | C1CCCNCC1 | C1CCC[NH]CC1 | C1CCC[NH]CC1 | HBr | C(C)#N | 50 | null | CCC(Br)C(=O)OC(C)(C)C.CCOC(=O)C1CCNC(=O)CC1>C(C)#N>CCOC(=O)C1CCC(=O)N(C(CC)C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-645ca911aca9427b9ef5667e682c5d11 | CCOC(=O)C1CCC(=O)N(C(CC)C(=O)OC(C)(C)C)CC1>>CCOC(=O)C1CCC(=O)N(C(CC)C(=O)O)CC1 | C(C)(C)(C)OC(=O)C(CC)N1CCC(CCC1=O)C(=O)OCC.FC(C(=O)O)(F)F>>C(C)OC(=O)C1CCC(N(CC1)C(C(=O)O)CC)=O | CC(C)(C)[O:17][C:15]([CH:12]([N:11]1[C:9](=[O:10])[CH2:8][CH2:7][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:19][CH2:18]1)[CH2:13][CH3:14])=[O:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][C:9](=[O:10])[N:11]([CH:12]([CH2:13][CH3:14])[C:15](=[O:16])[OH:17])[CH2:18][CH2:19]1 | CCOC(=O)C1CCC(=O)N(C(CC)C(=O)OC(C)(C)C)CC1 | CCOC(=O)C1CCC(=O)N(C(CC)C(=O)O)CC1 | null | null | C(Cl)Cl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | O=C1CCCCCN1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | 0 | CELSIUS | 24 | HOUR | In a 25 ml three necked flask fitted with magnetic stirrer and dropping funnel under inert atmosphere, 1 g (3.1 mmoles) of pure ethyl 1-[1-(tert-butoxycarbonyl)propyl]-7-oxo-4-azepanecarboxylate 29 was dissolved in 5 ml of CH2Cl2. The mixture was cooled down to 0° C., 5 ml of trifluoroacetic acid was added. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | C1CCC[NH]CC1 | Other | C(Cl)Cl | 0 | 24 | CCOC(=O)C1CCC(=O)N(C(CC)C(=O)OC(C)(C)C)CC1>C(Cl)Cl>CCOC(=O)C1CCC(=O)N(C(CC)C(=O)O)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a657f347ef0e49a29c12131dbb390714 | C=CC(=O)Cl.Cc1cccc(C(=O)NC(C)C)c1N>>C=CC(=O)Nc1c(C)cccc1C(=O)NC(C)C | CN(C)C1=NC=CC=C1.NC1=C(C(=O)NC(C)C)C=CC=C1C.C(C)N(CC)CC.C(C=C)(=O)Cl.C(C=C)(=O)Cl>>CC=1C(=C(C(=O)NC(C)C)C=CC1)NC(C=C)=O | Cl[C:3]([CH:2]=[CH2:1])=[O:4].[NH2:5][c:6]1[c:7]([CH3:8])[cH:9][cH:10][cH:11][c:12]1[C:13](=[O:14])[NH:15][CH:16]([CH3:17])[CH3:18]>>[CH2:1]=[CH:2][C:3](=[O:4])[NH:5][c:6]1[c:7]([CH3:8])[cH:9][cH:10][cH:11][c:12]1[C:13](=[O:14])[NH:15][CH:16]([CH3:17])[CH3:18] | C=CC(=O)Cl.Cc1cccc(C(=O)NC(C)C)c1N | C=CC(=O)Nc1c(C)cccc1C(=O)NC(C)C | null | null | ClCCl.Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4].[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11]>>[#7:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C;D1;H2:4]):[c:11] | 52.4 | [{"value": 52.4, "product": "CC=1C(=C(C(=O)NC(C)C)C=CC1)NC(C=C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | To a solution of the title compound of Step B (0.93 g, 4.8 mmol) in dichloromethane (10 mL) was added triethylamine (0.876 mL, 6.2 mmol) and the mixture was cooled to 0° C. Acryloyl chloride (0.433 mL, 5.3 mmol) was then added and the mixture was warmed to ambient temperature and stirred overnight. Dimethylaminopyridin... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1 | HCl | ClCCl.Cl | 0 | 8 | C=CC(=O)Cl.Cc1cccc(C(=O)NC(C)C)c1N>ClCCl.Cl>C=CC(=O)Nc1c(C)cccc1C(=O)NC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a1a53def4c664a96999097c0e8311779 | COC(=O)C=O.NNc1ccccc1Cl>>COC(=O)/C=N/Nc1ccccc1Cl | C(C=O)(=O)OC.Cl.ClC1=C(C=CC=C1)NN>>ClC1=C(C=CC=C1)N\N=C\C(=O)OC | O=[CH:5][C:3]([O:2][CH3:1])=[O:4].[NH2:6][NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[Cl:14]>>[CH3:1][O:2][C:3](=[O:4])/[CH:5]=[N:6]/[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[Cl:14] | COC(=O)C=O.NNc1ccccc1Cl | COC(=O)/C=N/Nc1ccccc1Cl | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | c78be09cf200f3a07b02946ce0bbc22b647e9aaae7494d0480373904a4f330a9 | c3cbc07b90655a7aa9777b584274a03a2ec0cff34c5b5edc214a16916fe29f1c | c1ccccc1 | O=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[NH2;D1;+0:6]-[#7:7]-[c:8]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])/[CH;D2;+0:1]=[N;H0;D2;+0:6]/[#7:7]-[c:8] | null | [] | null | null | null | null | To a solution of methyl glyoxylate (6.8 g, 77 mmol) in methanol (150 mL) was added 2-chlorophenylhydrazine hydrochloride (12.5 g, 77 mmol) and the mixture was heated at reflux overnight, cooled and concentrated. The residue was re-dissolved in toluene and concentrated to give the title compound of Step A.
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aldehyde | Hydrazone | null | null | c1ccccc1 | HO- | CO | null | null | COC(=O)C=O.NNc1ccccc1Cl>CO>COC(=O)/C=N/Nc1ccccc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a30fcfbaca0f4f4f879d97038b13ac03 | COC(=O)/C=N/Nc1ccccc1Cl.O=C1CCC(=O)N1Br>>COC(=O)/C(Br)=N/Nc1ccccc1Cl | ClC1=C(C=CC=C1)N\N=C\C(=O)OC.BrN1C(CCC1=O)=O>>Br\C(\C(=O)OC)=N/NC1=C(C=CC=C1)Cl | [CH3:1][O:2][C:3](=[O:4])/[CH:5]=[N:7]/[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[Cl:15].O=C1CCC(=O)N1[Br:6]>>[CH3:1][O:2][C:3](=[O:4])/[C:5]([Br:6])=[N:7]/[NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[Cl:15] | COC(=O)/C=N/Nc1ccccc1Cl.O=C1CCC(=O)N1Br | COC(=O)/C(Br)=N/Nc1ccccc1Cl | null | null | O1CCCC1 | Functional Group Interconversion | Bromination | a7c00719e839face56bb6216cdade7363196489e7c6b7cc1c5406f7f68c2c5a7 | 68cd054524e636d74778502f9e7f5c5bef9bcf9a0813a8a4bfdcfd2b317bdb5c | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[C;D1;H3:2]-[#8:3]-[C:4](=[O;D1;H0:5])/[CH;D2;+0:6]=[#7:7]/[#7:8]-[c:9]>>[Br;H0;D1;+0:1]/[C;H0;D3;+0:6](=[#7:7]\[#7:8]-[c:9])-[C:4](=[O;D1;H0:5])-[#8:3]-[C;D1;H3:2] | 71.3 | [{"value": 71.3, "product": "Br\\C(\\C(=O)OC)=N/NC1=C(C=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of the title compound of Step A (16.5 g, 77 mmol) in tetrahydrofuran (150 mL) was added N-bromosuccinimide (13.7 g, 77 mmol) and the mixture was stirred at ambient temperature for 2 hours. The mixture was concentrated and extracted with hexane and the hexane solution was concentrated to give the title com... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ester.Tertiary amide.Tertiary amide | Hydrazone.Alkenyl halide | C1CCNC1 | null | c1ccccc1 | HO- | O1CCCC1 | null | 2 | COC(=O)/C=N/Nc1ccccc1Cl.O=C1CCC(=O)N1Br>O1CCCC1>COC(=O)/C(Br)=N/Nc1ccccc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b62c82ce4a9f497c902d1d7f12e1a2c2 | CC(c1ccccc1)n1ccnc1.O=C1CCN(Cc2ccccc2)CC1>>OC1(c2nccn2CCc2ccccc2)CCN(Cc2ccccc2)CC1 | C1(=CC=CC=C1)CN1CCC(CC1)=O.C1(=CC=CC=C1)C(C)N1C=NC=C1.C(CCC)[Li].CCCCCC>>C1(=CC=CC=C1)CCN1C(=NC=C1)C1(CCN(CC1)CC1=CC=CC=C1)O | [cH:3]1[n:4][cH:5][cH:6][n:7]1[CH:8]([CH3:9])[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[O:1]=[C:2]1[CH2:16][CH2:17][N:18]([CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][CH2:27]1>>[OH:1][C:2]1([c:3]2[n:4][cH:5][cH:6][n:7]2[CH2:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17][N:18]([C... | CC(c1ccccc1)n1ccnc1.O=C1CCN(Cc2ccccc2)CC1 | OC1(c2nccn2CCc2ccccc2)CCN(Cc2ccccc2)CC1 | null | null | C1CCOC1.O | C-C Coupling | OtherReaction | 104c0d12140db71c4a07a78a0bc19d9e90210ce156ef7bb9b397b7f586769b88 | 454f67ba8644982dc9f605915a0f36178771eadaffb50d3f1e0f17f2b6fdeb10 | c1ccc(CCn2ccnc2C2CCN(Cc3ccccc3)CC2)cc1 | [CH3;D1;+0:1]-[CH;D3;+0:2](-[#7;a:3]1:[c:4]:[c:5]:[#7;a:6]:[cH;D2;+0:7]:1)-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12].[O;H0;D1;+0:13]=[C;H0;D3;+0:14]1-[C:15]-[C:16]-[#7:17]-[C:18]-[C:19]-1>>[OH;D1;+0:13]-[C;H0;D4;+0:14]1(-[c;H0;D3;+0:7]2:[#7;a:6]:[c:5]:[c:4]:[#7;a:3]:2-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:8](:[c:9]... | 75 | [{"value": 75.0, "product": "C1(=CC=CC=C1)CCN1C(=NC=C1)C1(CCN(CC1)CC1=CC=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.0, "product": "C1(=CC=CC=C1)CCN1C(=NC=C1)C1(CCN(CC1)CC1=CC=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | null | null | A mixture of DIPA (1.4 mol) in THF (3000 ml) was stirred at −70° C. under N2 flow. Butyllithium 2.5 M/hexane (1.3 mol) was added portionwise at a temperature below −40° C. The mixture was stirred at −70° C. for 15 min. 1-phenylethyl-1H-imidazole (1 mol) dissolved in THF was added dropwise at a temperature below −55° C.... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Tertiary alcohol | c1c[nH]cn1.c1ccccc1.C1CC[NH]CC1 | c1ncc[nH]1.c1ccccc1.C1CC[NH]CC1 | c1ncc[nH]1.c1ccccc1.C1CC[NH]CC1.c1ccccc1 | null | C1CCOC1.O | -70 | null | CC(c1ccccc1)n1ccnc1.O=C1CCN(Cc2ccccc2)CC1>C1CCOC1.O>OC1(c2nccn2CCc2ccccc2)CCN(Cc2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-36dcda66a7bc4f35af86da77d22e3518 | OC1(c2nccn2Cc2ccccc2)CCN(Cc2ccccc2)CC1.[Cl-].[Cl-]>>Cl.Cl.c1ccc(CN2CCC3(CC2)c2ccccc2Cn2ccnc23)cc1 | [OH-].[Na+].C1(=CC=CC=C1)CN1CCC(CC1)(O)C=1N(C=CN1)CC1=CC=CC=C1.[Al+3].[Cl-].[Cl-].[Cl-].[Al+3].[Cl-].[Cl-].[Cl-]>>Cl.Cl.C1(=CC=CC=C1)CN1CCC2(CC1)C=1N(CC=3C=CC=CC32)C=CN1 | O[C:11]1([c:25]2[n:21]([CH2:20][c:19]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:22][cH:23][n:24]2)[CH2:10][CH2:9][N:8]([CH2:7][c:6]2[cH:5][cH:4][cH:3][cH:27][cH:26]2)[CH2:13][CH2:12]1.[Cl-:2].[Cl-:1]>>[ClH:1].[ClH:2].[cH:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[CH2:9][CH2:10][C:11]3([CH2:12][CH2:13]2)[c:14]2[cH:15][cH:16][cH:... | OC1(c2nccn2Cc2ccccc2)CCN(Cc2ccccc2)CC1.[Cl-].[Cl-] | Cl.Cl.c1ccc(CN2CCC3(CC2)c2ccccc2Cn2ccnc23)cc1 | null | null | null | C-C Coupling | OtherReaction | 57f4cf808426353a6122d5db873756c3882c9b4bca5ffeb055984b6b79f55f16 | 80806390361076ffee90cd775b1e87663148d08d65f5b27bdd06ebc36de07186 | c1ccc(CN2CCC3(CC2)c2ccccc2Cn2ccnc23)cc1 | O-[C;H0;D4;+0:1]1(-[c:2]2:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:2-[C:7]-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12])-[C:13]-[C:14]-[#7:15]-[C:16]-[C:17]-1.[Cl-;H0;D0:18].[Cl-;H0;D0:19]>>[ClH;D0;+0:19].[ClH;D0;+0:18].[c:12]:[c:11]:[c;H0;D3;+0:10]1:[c:8](:[c:9])-[C:7]-[#7;a:6]2:[c:5]:[c:4]:[#7;a:3]:[c:2]:2-[C;H0;D4;+0:1]-12-[C:13]... | 1.8 | [{"value": 1.8, "product": "Cl.Cl.C1(=CC=CC=C1)CN1CCC2(CC1)C=1N(CC=3C=CC=CC32)C=CN1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 1 | HOUR | 1-(phenylmethyl)-4-[1-(phenylmethyl)-1H-imidazol-2-yl]-4-piperidinol (0.124 mol) and AlCl3 (0.31 mol) were stirred in a melt at 120° C. for 1 h. The mixture was cooled, AlCl3 (0.31 mol) was added and the mixture was stirred at 120° C. for 1 h. The mixture was poured into ice, alkalized with NaOH 50% and extracted with ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | c1ccccc1.C1CC[NH]CC1 | c1ccc2c(c1)Cn1ccnc1C21CC[NH]CC1 | c1ccccc1.c1ccc2c(c1)Cn1ccnc1C21CC[NH]CC1 | Other | null | 120 | 1 | OC1(c2nccn2Cc2ccccc2)CCN(Cc2ccccc2)CC1.[Cl-].[Cl-]>>Cl.Cl.c1ccc(CN2CCC3(CC2)c2ccccc2Cn2ccnc23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-208c125703734caba2a9259dcaadb6cc | CN1CCC(C(=O)Cl)(c2ccccc2)CC1.NCc1ccccc1>>CN1CCC(C(=O)NCc2ccccc2)(c2ccccc2)CC1 | CN1CCC(CC1)(C(=O)Cl)C1=CC=CC=C1.C1(=CC=CC=C1)CN.C(C)N(CC)CC.C(=O)([O-])[O-].[K+].[K+]>>CN1CCC(CC1)(C(=O)NCC1=CC=CC=C1)C1=CC=CC=C1 | Cl[C:6]([C:5]1([c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:4][CH2:3][N:2]([CH3:1])[CH2:23][CH2:22]1)=[O:7].[NH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][N:2]1[CH2:3][CH2:4][C:5]([C:6](=[O:7])[NH:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)([c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[... | CN1CCC(C(=O)Cl)(c2ccccc2)CC1.NCc1ccccc1 | CN1CCC(C(=O)NCc2ccccc2)(c2ccccc2)CC1 | null | null | O.C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1ccccc1)C1(c2ccccc2)CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])(-[C:5])-[C:6].[NH2;D1;+0:7]-[C:8]-[c:9]>>[C:5]-[C:3](-[c:4])(-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:8]-[c:9])-[C:6] | 95.3 | [{"value": 95.0, "product": "CN1CCC(CC1)(C(=O)NCC1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.3, "product": "CN1CCC(CC1)(C(=O)NCC1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 1-Methyl-4-phenyl-4-piperidinecarbonyl chloride (0.49 mol) was added portionwise at room temperature to a stirring mixture of benzenemethanamine (0.49 mol) and triethyl amine (1.223 mol) in CH2Cl2 (2500 ml). The mixture was stirred at room temperature for 1 hour. K2CO3 (150 g) and H2O were added. The mixture was stirre... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.c1ccccc1.c1ccccc1 | HCl | O.C(Cl)Cl | null | 1 | CN1CCC(C(=O)Cl)(c2ccccc2)CC1.NCc1ccccc1>O.C(Cl)Cl>CN1CCC(C(=O)NCc2ccccc2)(c2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-696b82fd9a0a4806818870df0e9948e3 | CN(C)C=O.c1ccc(CCCCn2ccnc2)cc1>>NC(=O)c1nccn1CCCCc1ccccc1 | [NH4+].[Cl-].CN(C=O)C.C(CCC)[Li].CCCCCC.C1(=CC=CC=C1)CCCCN1C=NC=C1>>C1(=CC=CC=C1)CCCCN1C(=NC=C1)C(=O)N | C[N:1](C)[CH:2]=[O:3].[cH:4]1[n:5][cH:6][cH:7][n:8]1[CH2:9][CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[NH2:1][C:2](=[O:3])[c:4]1[n:5][cH:6][cH:7][n:8]1[CH2:9][CH2:10][CH2:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | CN(C)C=O.c1ccc(CCCCn2ccnc2)cc1 | NC(=O)c1nccn1CCCCc1ccccc1 | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 7f57a7521d1baa0851e1141ce1cea38ee563de57b44f5f72d186fcb0ae1b20dd | 2b96b5a9b8a7ea9a2f788a30832f4ff1c689451b5a72ad75fa45cd01ef4810db | c1ccc(CCCCn2ccnc2)cc1 | C-[N;H0;D3;+0:1](-C)-[CH;D2;+0:2]=[O;D1;H0:3].[C:4]-[#7;a:5]1:[c:6]:[c:7]:[#7;a:8]:[cH;D2;+0:9]:1>>[C:4]-[#7;a:5]1:[c:6]:[c:7]:[#7;a:8]:[c;H0;D3;+0:9]:1-[C;H0;D3;+0:2](-[NH2;D1;+0:1])=[O;D1;H0:3] | null | [] | -78 | CELSIUS | null | null | Reaction under N2 atmosphere. A mixture of DIPA (0.455 mol) in THF (500 ml) was stirred at −78° C. Butyllithium, 2.5M/hexane (0.390 mol) was added dropwise at −40° C. The mixture was stirred for 15 min, then re-cooled to −78° C. A solution of 1-(4-phenylbutyl)-1H-imidazole, prepared according to the procedure described... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Primary amide | c1c[nH]cn1 | c1ncc[nH]1 | c1ncc[nH]1.c1ccccc1 | Other | C1CCOC1 | -78 | null | CN(C)C=O.c1ccc(CCCCn2ccnc2)cc1>C1CCOC1>NC(=O)c1nccn1CCCCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ebdb6c09cb774332a0a1cecc00fe64cd | CN(C)C=O.Oc1cc2c(cc1O)Cn1ccnc1C2>>COc1cc2c(cc1OC)Cn1ccnc1C2 | O.N=1C=CN2CC=3C=C(C(=CC3CC21)O)O.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>>COC=1C(=CC=2CC=3N(CC2C1)C=CN3)OC | CN([CH:1]=O)[CH3:10].[OH:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[OH:9])[CH2:11][n:12]1[cH:13][cH:14][n:15][c:16]1[CH2:17]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[O:9][CH3:10])[CH2:11][n:12]1[cH:13][cH:14][n:15][c:16]1[CH2:17]2 | CN(C)C=O.Oc1cc2c(cc1O)Cn1ccnc1C2 | COc1cc2c(cc1OC)Cn1ccnc1C2 | null | [Cl-].C1(=CC=CC=C1)[N+](C)(C)C | null | Heteroatom Alkylation and Arylation | OtherReaction | 05add0336860651e77560062fbde59de7637be14641b2137a48bb7a130e673d5 | 70540f8b47d0cb308c47727b03916eb5873a3febfc3e6645bdd3176ffa63991d | c1ccc2c(c1)Cc1nccn1C2 | C-N(-[CH3;D1;+0:1])-[CH;D2;+0:2]=O.[OH;D1;+0:3]-[c:4](:[c:5]):[c:6](-[OH;D1;+0:7]):[c:8]>>[CH3;D1;+0:1]-[O;H0;D2;+0:7]-[c:6](:[c:8]):[c:4](-[O;H0;D2;+0:3]-[CH3;D1;+0:2]):[c:5] | 8.4 | [{"value": 8.4, "product": "COC=1C(=CC=2CC=3N(CC2C1)C=CN3)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5,10-dihydro-imidazo[1,2-b]-isoquinoline-7,8-diol, obtained according to the procedure described in Ex.No. A8 c, (0.155 mol), phenyltrimethylammonium chloride (0.31 mol) and K2CO3 (0.68 mol) in DMF (400 ml) was stirred at 90° C. for 20 hours, cooled, poured out into H2O and filtered over dicalite. The filt... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Aromatic alcohol.Aromatic alcohol | Ether.Ether | null | null | c1ccc2c(c1)Cc1nccn1C2 | HO- | [Cl-].C1(=CC=CC=C1)[N+](C)(C)C | null | null | CN(C)C=O.Oc1cc2c(cc1O)Cn1ccnc1C2>[Cl-].C1(=CC=CC=C1)[N+](C)(C)C>COc1cc2c(cc1OC)Cn1ccnc1C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-825838bf0675463188070eeb1a8507bd | C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@H]43)[C@@H]1CC[C@@H]2O>>C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(=O)CC[C@@H]43)[C@@H]1CC[C@@H]2O | CCCCCCCC(=O)C(C(=O)CCCCCCC)(C(=O)CCCCCCC)[NH3+].[Cl-].C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=O)CC[C@H]34>>O[C@@H]1[C@]2(C)[C@@H](CC1)[C@@H]1CC[C@@H]3CC(CC[C@@H]3[C@H]1CC2)=O | [CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]3[C@@H:6]([CH2:7][CH2:8][C:9]4=[CH:10][C:11](=[O:12])[CH2:13][CH2:14][C@H:15]34)[C@@H:16]1[CH2:17][CH2:18][C@@H:19]2[OH:20]>>[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]3[C@@H:6]([CH2:7][CH2:8][C@@H:9]4[CH2:10][C:11](=[O:12])[CH2:13][CH2:14][C@H:15]34)[C@@H:16]1[CH2:17][CH2:18][C@@H:19]2[OH:... | C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@H]43)[C@@H]1CC[C@@H]2O | C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(=O)CC[C@@H]43)[C@@H]1CC[C@@H]2O | null | null | ClCCl.O | Reduction | Hydrogenation (double to single) | 57601b680323e405817ba7605c71f4c533dd9299fe6c475cc1627ae4949cdd43 | 0e0db21233797ec1d2a9464a1f32cef94e53e6a41f96d680fa1307067bbf01f2 | O=C1CC[C@H]2[C@H](CC[C@@H]3[C@@H]2CCC2CCC[C@H]23)C1 | [C:1]-[C:2]1-[C:3]-[C:4]-[C:5](=[O;D1;H0:6])-[CH;D2;+0:7]=[C;H0;D3;+0:8]-1-[C:9]-[C:10]>>[C:1]-[C:2]1-[C:3]-[C:4]-[C:5](=[O;D1;H0:6])-[CH2;D2;+0:7]-[C@H;D3;+0:8]-1-[C:9]-[C:10] | 107 | [{"value": 92.0, "product": "O[C@@H]1[C@]2(C)[C@@H](CC1)[C@@H]1CC[C@@H]3CC(CC[C@@H]3[C@H]1CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 107.0, "product": "O[C@@H]1[C@]2(C)[C@@H](CC1)[C@@H]1CC[C@@H]3CC(CC[C@@H]3[C@H]1CC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 19-nortestosterone (10.0 g, 35.5 mmol) in dichloromethane (100.0 ml) was mixed with the catalyst previously prepared from RhCl3.H2O (380 mg) and Aliquat-336® (800 mg) in water (10.0 ml) and dichloromethane (22.0 ml). The mixture was hydrogenated overnight at 20 psi. The product was washed twice with water... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone | C1=C2CC[C@H]3[C@@H]4CCC[C@@H]4CC[C@@H]3[C@H]2CCC1 | C1CC[C@H]2[C@@H](C1)CC[C@@H]1[C@@H]2CC[C@H]2CCC[C@H]21 | C1CC[C@H]2[C@@H](C1)CC[C@@H]1[C@@H]2CC[C@H]2CCC[C@H]21 | null | ClCCl.O | null | 8 | C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@H]43)[C@@H]1CC[C@@H]2O>ClCCl.O>C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(=O)CC[C@@H]43)[C@@H]1CC[C@@H]2O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-faa2f348d6f5478eb5c5bd468fd5e72f | C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC2=O.OCCO>>C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC21OCCO1 | C(CO)O.C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[NH+]1=CC=CC=C1.CCOC(=O)C.CCCCCC.OC1C[C@H]2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@H]2CC1)=O>>C1COC2([C@]3(C)[C@@H](CC2)[C@@H]2CC[C@@H]4CC(CC[C@@H]4[C@H]2CC3)O)O1 | [CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]3[C@@H:6]([CH2:7][CH2:8][C@@H:9]4[CH2:10][CH:11]([OH:12])[CH2:13][CH2:14][C@H:15]34)[C@@H:16]1[CH2:17][CH2:18][C:19]2=[O:20].O[CH2:21][CH2:22][OH:23]>>[CH3:1][C@:2]12[CH2:3][CH2:4][C@H:5]3[C@@H:6]([CH2:7][CH2:8][C@@H:9]4[CH2:10][CH:11]([OH:12])[CH2:13][CH2:14][C@H:15]34)[C@@H:16]1[CH... | C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC2=O.OCCO | C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC21OCCO1 | null | null | CCOC(=O)C.C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 41ae5195ba47d3db987aa5d31e3b31b1e97aef93f007000a7df7639fc806d9f0 | f8121a7732f8ef583111433d2b2d82886bf3a134c51dc6363d813c8cbf4e36f5 | C1CC[C@H]2[C@@H](C1)CC[C@@H]1[C@@H]2CCC2[C@H]1CCC21OCCO1 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].[C:4]-[C:5]1(-[C;D1;H3:6])-[C:7]-[C:8]-[C:9]-[C;H0;D3;+0:10]-1=[O;H0;D1;+0:11]>>[C:4]-[C:5]1(-[C;D1;H3:6])-[C:7]-[C:8]-[C:9]-[C;H0;D4;+0:10]-12-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-2 | 94.8 | [{"value": 94.5, "product": "C1COC2([C@]3(C)[C@@H](CC2)[C@@H]2CC[C@@H]4CC(CC[C@@H]4[C@H]2CC3)O)O1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.8, "product": "C1COC2([C@]3(C)[C@@H](CC2)[C@@H]2CC[C@@H]4CC(CC[C@@H]4[C@H]2CC3)O)O1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Compound 4(10 g, 36.2 mmol) was dissolved in dry benzene (150 ml) mixed with ethylene glycol (25 ml, 280 mmol) and pyridinium p-toluenesulfonate (1 g, 3.9 mmol) and refluxed using a Dean-stark separator overnight till no starting material was detected by TLC. The cold solution was diluted with EtOAc (100 ml), washed tw... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary alcohol.Primary alcohol | Ether.Ether | C1CC[C@H]2[C@@H](C1)CC[C@@H]1[C@@H]2CC[C@H]2CCC[C@H]21 | C1CC[C@H]2[C@@H](C1)CC[C@@H]1[C@@H]2CC[C@@H]2[C@H]1CCC21OCCO1 | C1CC[C@H]2[C@@H](C1)CC[C@@H]1[C@@H]2CC[C@@H]2[C@H]1CCC21OCCO1 | HO- | CCOC(=O)C.C1=CC=CC=C1 | null | 8 | C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC2=O.OCCO>CCOC(=O)C.C1=CC=CC=C1>C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC21OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-347b46abced84de9bf8ce6a178260fd5 | CCOC=C(C(=O)OCC)C(=O)OCC.CSC(=N)N>>CCOC(=O)c1cnc(SC)nc1O | [OH-].[Na+].CSC(=N)N.OS(=O)(=O)O.C(C)OC=C(C(=O)OCC)C(=O)OCC>>CSC1=NC=C(C(=N1)O)C(=O)OCC | CCO[CH:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:13](OCC)=[O:14].[NH2:8][C:9]([S:10][CH3:11])=[NH:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([S:10][CH3:11])[n:12][c:13]1[OH:14] | CCOC=C(C(=O)OCC)C(=O)OCC.CSC(=N)N | CCOC(=O)c1cnc(SC)nc1O | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | caf9cb78c7502ec533d5fe3b7a8a08e1fb6cf99301dd7b428451735db624aa4a | 06f73c43becdfac6f63abd2370cc1e14a2a3568880484871cbc0fc9a1c48b1b0 | c1cncnc1 | C-C-O-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-O-C-C.[C;D1;H3:9]-[#16:10]-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[NH;D1;+0:13]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D2;+0:12]:[c;H0;D3;+0:11](-[#16:10]-[C;D1;H3:9]):[n;H0;D2;+0:13]:[c;H0;D3;+0... | 61 | [{"value": 61.0, "product": "CSC1=NC=C(C(=N1)O)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.7, "product": "CSC1=NC=C(C(=N1)O)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a 4N sodium hydroxide solution (200 mL) was added S-methylisothioureasulfate (55.6 g, 0.2 mol), and after stirring for 30 min, at room temperature a solution of diethyl ethoxymethylenemalonate (80.8 mL, 0.35 mol) in ethanol (100 mL) was dropwise added slowly over 1 h. After stirring for 18 h, the precipitated crysta... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Primary amine.Monosulfide | Ester.Aromatic alcohol.Monosulfide | null | c1cncnc1 | c1cncnc1 | HO- | C(C)O | null | 18 | CCOC=C(C(=O)OCC)C(=O)OCC.CSC(=N)N>C(C)O>CCOC(=O)c1cnc(SC)nc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b3ebf651e99d40be9d11ee0c8e9016bb | CCOC(=O)c1cnc(SC)nc1O.c1ccc2c(c1)CCN2>>CCOC(=O)c1cnc(N2CCc3ccccc32)nc1O | N1CCC2=CC=CC=C12.CSC1=NC=C(C(=N1)O)C(=O)OCC>>OC1=NC(=NC=C1C(=O)OCC)N1CCC2=CC=CC=C12 | CS[c:9]1[n:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:20]([OH:21])[n:19]1.[NH:10]1[CH2:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[n:19][c:20]1[OH:21] | CCOC(=O)c1cnc(SC)nc1O.c1ccc2c(c1)CCN2 | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1O | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 4505c639bebc45c428c7c95a2ea93278a0c93ae321cd06f8fa554f9f2513cd5d | f5aa33108984aad43441754644c214239e577e2035dc027b4aa13ab85821a21b | c1cnc(N2CCc3ccccc32)nc1 | C-S-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[c:6]:[c:7]1:[c:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[c:6]:[c:7]1:[c:8]-[C:9]-[C:10]-[N;H0;D3;+0:11]-1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 77.1 | [{"value": 77.0, "product": "OC1=NC(=NC=C1C(=O)OCC)N1CCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.1, "product": "OC1=NC(=NC=C1C(=O)OCC)N1CCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of indoline (3.58 g, 30 mmol) in ethanol (50 mL) was added ethyl 2-methylthio-4-hydroxypyrimidine-5-carboxylate (5.35 g, 25 mmol) and the mixture was heated under reflux for 18 h. The reaction mixture was allowed to cool to room temperature and the precipitated crystals were collected by filtration. The c... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Monosulfide | Tertiary amine | c1cncnc1.c1ccc2c(c1)CCN2 | c1cncnc1.c1ccc2c(c1)CC[NH]2 | c1cncnc1.c1ccc2c(c1)CC[NH]2 | Other | C(C)O | null | null | CCOC(=O)c1cnc(SC)nc1O.c1ccc2c(c1)CCN2>C(C)O>CCOC(=O)c1cnc(N2CCc3ccccc32)nc1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-05fcf5b00c234f1c840e80e373f6affb | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1O.Fc1ccc(CBr)cc1>>CCOC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1 | O.OC1=NC(=NC=C1C(=O)OCC)N1CCC2=CC=CC=C12.C([O-])([O-])=O.[K+].[K+].FC1=CC=C(CBr)C=C1>>N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)F)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[n:19][c:20]1[OH:21].Br[CH2:22][c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c... | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1O.Fc1ccc(CBr)cc1 | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccnc(N3CCc4ccccc43)n2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1-[OH;D1;+0:14]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1-[O;H0;D2;+0:14]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 79.2 | [{"value": 79.0, "product": "N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)F)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.2, "product": "N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)F)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 18 | HOUR | To a solution of ethyl 4-hydroxy-2-(2,3-dihydro-1H-indol-1-yl)-5-pyrimidinecarboxylate (7.1 g, 27.6 mmol) in N,N-dimethylformamide (100 ml) were added potassium carbonate (7.8 g, 60 mmol) and 4-fluorobenzylbromide (3.74 ml, 30 mmol) and the mixture was stirred at 80° C. for 18 h. The reaction mixture was allowed to coo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1cncnc1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | HBr | CN(C=O)C | 80 | 18 | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1O.Fc1ccc(CBr)cc1>CN(C=O)C>CCOC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4b9b0f31ba6b4ff9aace7ffd9d916a47 | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1O.COc1ccc(CCl)cc1>>CCOC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(OC)cc1 | OC1=NC(=NC=C1C(=O)OCC)N1CCC2=CC=CC=C12.C([O-])([O-])=O.[K+].[K+].[I-].[Na+].COC1=CC=C(CCl)C=C1>>N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)OC)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[n:19][c:20]1[OH:21].Cl[CH2:22][c:23]1[cH:24][cH:25][c:26]([O:27][CH3:28])[cH:29][cH:30]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][... | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1O.COc1ccc(CCl)cc1 | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(OC)cc1 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(COc2ccnc(N3CCc4ccccc43)n2)cc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1-[OH;D1;+0:14]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1-[O;H0;D2;+0:14]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 78 | [{"value": 78.0, "product": "N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)OC)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.5, "product": "N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)OC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 18 | HOUR | To a solution of ethyl 4-hydroxy-2-(2,3-dihydro-1H-indol-1-yl)-5-pyrimidinecarboxylate (500 mg, 1.75 mmol) in N,N-dimethylformamide (10 mL) were added potassium carbonate (500 g, 4 mmol), sodium iodide (300 mg, 2 mmol) and 4-methoxybenzyl chloride (0.29 mL, 2 mmol), and the mixture was stirred at 80° C. for 18 h. The r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1cncnc1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | HCl | O.CN(C=O)C | 80 | 18 | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1O.COc1ccc(CCl)cc1>O.CN(C=O)C>CCOC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b563b66a76d47b3b1470b157246b957 | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1O.O=P(Cl)(Cl)Cl>>CCOC(=O)c1cnc(N2CCc3ccccc32)nc1Cl | OC1=NC(=NC=C1C(=O)OCC)N1CCC2=CC=CC=C12.P(=O)(Cl)(Cl)Cl>>ClC1=NC(=NC=C1C(=O)OCC)N1CCC2=CC=CC=C12 | O[c:20]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[n:19]1.O=P(Cl)(Cl)[Cl:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[n:19][c:20]1[Cl:21] | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1O.O=P(Cl)(Cl)Cl | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1Cl | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | c34cc3a735ba90a6ebc3a31af86c6a0085713d9dcab569055caa3b8d444bb07d | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1cnc(N2CCc3ccccc32)nc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4](-[#7:5]):[#7;a:6]:[c:7]:[c:8]:1-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]>>[#7:5]-[c:4]1:[#7;a:3]:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[c:8](-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]):[c:7]:[#7;a:6]:1 | 477.4 | [{"value": 100.0, "product": "ClC1=NC(=NC=C1C(=O)OCC)N1CCC2=CC=CC=C12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 477.4, "product": "ClC1=NC(=NC=C1C(=O)OCC)N1CCC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 15 | HOUR | To ethyl 4-hydroxy-2-(2,3-dihydro-1H-indol-1-yl)-5-pyrimidinecarboxylate (2.85 g, 10 mmol) was added phosphorus oxychloride (10 mL, 2 mmol) and the mixture was stirred at 120° C. for 15 h. The reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate, washed with satu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)CC[NH]2 | HCl | null | 120 | 15 | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1O.O=P(Cl)(Cl)Cl>>CCOC(=O)c1cnc(N2CCc3ccccc32)nc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-47cbd00618f04a099dd5260bd5b784b4 | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1Cl.OCc1ccc(OC(F)(F)F)cc1>>CCOC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(OC(F)(F)F)cc1 | O.ClC1=NC(=NC=C1C(=O)OCC)N1CCC2=CC=CC=C12.C([O-])([O-])=O.[K+].[K+].FC(OC1=CC=C(CO)C=C1)(F)F>>N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)OC(F)(F)F)C(=O)OCC | Cl[c:20]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[n:19]1.[OH:21][CH2:22][c:23]1[cH:24][cH:25][c:26]([O:27][C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][c:13]3... | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1Cl.OCc1ccc(OC(F)(F)F)cc1 | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(OC(F)(F)F)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(COc2ccnc(N3CCc4ccccc43)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[OH;D1;+0:12]-[C:13]-[c:14]>>[#7:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:12]-[C:13]-[c:14]):[c:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]):[c:6]:[#7;a:5]:1 | 53.2 | [{"value": 53.0, "product": "N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)OC(F)(F)F)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.2, "product": "N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)OCC1=CC=C(C=C1)OC(F)(F)F)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 18 | HOUR | To a solution of ethyl 4-chloro-2-(2,3-dihydro-1H-indol-1-yl)-5-pyrimidinecarboxylate (520 mg, 1.72 mmol) in N,N-dimethylformamide (5 mL) was added potassium carbonate (829 mg, 6 mmol) and 4-(trifluoromethoxy)benzyl alcohol (384 mg, 2 mmol) and the mixture was stirred at 100° C. for 18 h. The reaction mixture was allow... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | HCl | CN(C=O)C | 100 | 18 | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1Cl.OCc1ccc(OC(F)(F)F)cc1>CN(C=O)C>CCOC(=O)c1cnc(N2CCc3ccccc32)nc1OCc1ccc(OC(F)(F)F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a61417b4a55b431fb3b5c4a7891ca0c1 | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1Cl.NCc1ccc(F)cc1>>CCOC(=O)c1cnc(N2CCc3ccccc32)nc1NCc1ccc(F)cc1 | O.ClC1=NC(=NC=C1C(=O)OCC)N1CCC2=CC=CC=C12.C([O-])([O-])=O.[Na+].[Na+].FC1=CC=C(CN)C=C1>>N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)NCC1=CC=C(C=C1)F)C(=O)OCC | Cl[c:20]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]32)[n:19]1.[NH2:21][CH2:22][c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([N:10]2[CH2:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17... | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1Cl.NCc1ccc(F)cc1 | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1NCc1ccc(F)cc1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc(N3CCc4ccccc43)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[NH2;D1;+0:12]-[C:13]-[c:14]>>[#7:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:12]-[C:13]-[c:14]):[c:7](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]):[c:6]:[#7;a:5]:1 | 81.2 | [{"value": 81.0, "product": "N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)NCC1=CC=C(C=C1)F)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.2, "product": "N1(CCC2=CC=CC=C12)C1=NC=C(C(=N1)NCC1=CC=C(C=C1)F)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of ethyl 4-chloro-2-(2,3-dihydro-1H-indol-1-yl)-5-pyrimidinecarboxylate (607 mg, 2.0 mmol) in isopropanol (5 mL) were added sodium carbonate (424 mg, 4 mmol) and 4-fluorobenzylamine (313 mg, 4 mmol) and the mixture was heated under reflux for 18 h. The reaction mixture was allowed to cool to room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | HCl | C(C)(C)O | null | null | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1Cl.NCc1ccc(F)cc1>C(C)(C)O>CCOC(=O)c1cnc(N2CCc3ccccc32)nc1NCc1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-246db8c799c144b3969777dadbb12e19 | COc1ccc2[nH]ccc2c1>>COc1ccc2c(c1)CCN2 | COC=1C=C2C=CNC2=CC1.C(#N)[BH3-].[Na+]>>COC=1C=C2CCNC2=CC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[cH:9][cH:10][nH:11]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][NH:11]2 | COc1ccc2[nH]ccc2c1 | COc1ccc2c(c1)CCN2 | null | null | C(C)(=O)O | Reduction | OtherReaction | d7c64ff5bdeff25897e9ebfc8baf5f34c2f69037fd4e91a3394e3e20a554de0e | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | c1ccc2c(c1)CCN2 | [c:1]:[c:2]1:[nH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6]:1:[c:7]>>[c:1]:[c:2]1:[c:6](:[c:7])-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[NH;D2;+0:3]-1 | 94 | [{"value": 94.0, "product": "COC=1C=C2CCNC2=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.7, "product": "COC=1C=C2CCNC2=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of 5-methoxyindole (528 mg, 3.6 mmol) in acetic acid (5 mL) was added sodium cyanoborohydride (452 mg, 7.2 mmol) by small portions at room temperature and the mixture was stirred for 18 h in situ. The solvent was evaporated under reduced pressure and the obtained residue was dissolved in ethyl acetate. Th... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccc2[nH]ccc2c1 | c1ccc2c(c1)CCN2 | c1ccc2c(c1)CCN2 | null | C(C)(=O)O | null | 18 | COc1ccc2[nH]ccc2c1>C(C)(=O)O>COc1ccc2c(c1)CCN2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-44c45998a8b849329f98083d33b92282 | O=C(O)C1Cc2ccccc2N1>>OCC1Cc2ccccc2N1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].N1C(CC2=CC=CC=C12)C(=O)O.C(C)O.Cl>>OCC1NC2=CC=CC=C2C1 | O=[C:2]([OH:1])[CH:3]1[CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[NH:11]1>>[OH:1][CH2:2][CH:3]1[CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[NH:11]1 | O=C(O)C1Cc2ccccc2N1 | OCC1Cc2ccccc2N1 | null | null | O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc2c(c1)CCN2 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3](-[C:4])-[#7:5]-[c:6]>>[C:4]-[C:3](-[CH2;D2;+0:1]-[O;D1;H1:2])-[#7:5]-[c:6] | 64.3 | [{"value": 64.0, "product": "OCC1NC2=CC=CC=C2C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.3, "product": "OCC1NC2=CC=CC=C2C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 18 | HOUR | To a solution of (RS)-indoline-2-carboxylic acid (8.16 g, 50 mmol) in tetrahydrofuran (50 ml) was added under ice-cooling lithium aluminum hydride (5.7 g, 150 mmol) and the mixture was stirred at 60° C. for 18 h. The reaction mixture was stirred under ice-cooling and ethanol and 1N hydrochloric acid were added. The pre... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccc2c(c1)CCN2 | Other | O1CCCC1 | 60 | 18 | O=C(O)C1Cc2ccccc2N1>O1CCCC1>OCC1Cc2ccccc2N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2d6bc2f5413f417781b69375e7336008 | O=C(O)c1ccc2c(c1)CCO2>>OCc1ccc2c(c1)CCO2 | [H-].[Al+3].[Li+].[H-].[H-].[H-].O1C2=C(CC1)C=C(C=C2)C(=O)O.CO.Cl>>O1C2=C(CC1)C=C(C=C2)CO | O=[C:2]([OH:1])[c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][O:11]2>>[OH:1][CH2:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][O:11]2 | O=C(O)c1ccc2c(c1)CCO2 | OCc1ccc2c(c1)CCO2 | null | null | O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc2c(c1)CCO2 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 100 | [{"value": 100.0, "product": "O1C2=C(CC1)C=C(C=C2)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.9, "product": "O1C2=C(CC1)C=C(C=C2)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | To a solution of 2,3-dihydrobenzo[b]furan-5-carboxylic acid (1.64 g, 10 mmol) in tetrahydrofuran (10 mL) was added under ice-cooling lithium aluminum hydride (949 mg, 25 mmol) and the mixture was stirred at 60° C. for 1 h. The reaction mixture was stirred under ice-cooling and methanol and 1N hydrochloric acid were add... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccc2c(c1)CCO2 | Other | O1CCCC1 | 60 | 1 | O=C(O)c1ccc2c(c1)CCO2>O1CCCC1>OCc1ccc2c(c1)CCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-481ec1a85eb24912b47c7efbb63a5f15 | CS(=O)(=O)Cl.OCc1ccc2c(c1)CCO2>>ClCc1ccc2c(c1)CCO2 | O1C2=C(CC1)C=C(C=C2)CO.C(C)N(CC)CC.CS(=O)(=O)Cl>>O1C2=C(CC1)C=C(C=C2)CCl | CS(=O)(=O)[Cl:1].O[CH2:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][O:11]2>>[Cl:1][CH2:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][O:11]2 | CS(=O)(=O)Cl.OCc1ccc2c(c1)CCO2 | ClCc1ccc2c(c1)CCO2 | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_sulfonyl chloride | 58d25ddf86b8daa38762ecb08ed922faa2d01716f69924f9b8413703fe1b3fc7 | d5d71bad4297b1f4f93dd1d1d9cddf0bb6fadb3f4dca1f84369c4074a39097d6 | c1ccc2c(c1)CCO2 | C-S(=O)(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 100 | [{"value": 100.0, "product": "O1C2=C(CC1)C=C(C=C2)CCl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.9, "product": "O1C2=C(CC1)C=C(C=C2)CCl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of (2,3-dihydrobenzo[b]furan-5-yl)methanol (1.5 g, 10 mmol) in dichloromethane (10 mL) were added under ice-cooling triethylamine (1.67 mL, 12 mmol) and methanesulfonyl chloride (0.85 mL, 10 mmol) and the mixture was stirred at room temperature for 1 h. The solvent was evaporated under reduced pressure an... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Primary halide | null | null | c1ccc2c(c1)CCO2 | HO- | ClCCl | null | 1 | CS(=O)(=O)Cl.OCc1ccc2c(c1)CCO2>ClCCl>ClCc1ccc2c(c1)CCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-32baeeeecd374a7189596c7a144284aa | CI.CN(C)C=O.O=C(O)c1ccc(O)c(Cl)c1>>COC(=O)c1ccc(OC)c(Cl)c1 | O.ClC=1C=C(C(=O)O)C=CC1O.C([O-])([O-])=O.[K+].[K+].CI.CN(C=O)C>>ClC=1C=C(C(=O)OC)C=CC1OC | I[CH3:1].CN(C=O)[CH3:10].[OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[c:11]([Cl:12])[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH3:10])[c:11]([Cl:12])[cH:13]1 | CI.CN(C)C=O.O=C(O)c1ccc(O)c(Cl)c1 | COC(=O)c1ccc(OC)c(Cl)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 4e302a5c4b5749a27005cfac332d21a67cd4b03cabc4b79c56523042a9f3f68a | 11e44eaefaffcf2f4bedaafd68334cfa44459302a483454fd2d2ec963968ffac | c1ccccc1 | C-N(-[CH3;D1;+0:1])-C=O.I-[CH3;D1;+0:2].[O;D1;H0:3]=[C:4](-[OH;D1;+0:5])-[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[CH3;D1;+0:2]-[O;H0;D2;+0:5]-[C:4](=[O;D1;H0:3])-[c:6].[CH3;D1;+0:1]-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | 100 | [{"value": 100.0, "product": "ClC=1C=C(C(=O)OC)C=CC1OC", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | HOUR | To a solution of 3-chloro-4-hydroxybenzoic acid (3.45 g, 20 mmol) in N,N-dimethylformamide (10 mL) were added potassium carbonate (6.9 g, 50 mmol) and methyl iodide (large excess) and the mixture was stirred at 60° C. for 2 h. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HI | null | 60 | 2 | CI.CN(C)C=O.O=C(O)c1ccc(O)c(Cl)c1>>COC(=O)c1ccc(OC)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2bf43f8c975c483f9da765c710675886 | COC(=O)c1ccc(OC)c(Cl)c1>>COc1ccc(CO)cc1Cl | ClC=1C=C(C(=O)OC)C=CC1OC.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>>ClC=1C=C(CO)C=CC1OC | CO[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:10]([Cl:11])[cH:9]1)=[O:8]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:9][c:10]1[Cl:11] | COC(=O)c1ccc(OC)c(Cl)c1 | COc1ccc(CO)cc1Cl | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 106.2 | [{"value": 100.0, "product": "ClC=1C=C(CO)C=CC1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 106.2, "product": "ClC=1C=C(CO)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of methyl 3-chloro-4-methoxybenzoate (1.2 g, 6 mmol) in tetrahydrofuran (10 ml) was added under ice-cooling lithium aluminum hydride (455 mg, 12 mmol) and the mixture was stirred at room temperature for 1 h. The reaction mixture was stirred under ice-cooling and 0.1N hydrochloric acid was added. The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | Other | O1CCCC1 | null | 1 | COC(=O)c1ccc(OC)c(Cl)c1>O1CCCC1>COc1ccc(CO)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e4e85b88e8b940a682a714ca09b108c4 | COc1ccc(CO)cc1Cl.CS(=O)(=O)Cl>>COc1ccc(CCl)cc1Cl | ClC=1C=C(CO)C=CC1OC.C(C)N(CC)CC.CS(=O)(=O)Cl>>ClC=1C=C(CCl)C=CC1OC | O[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:10]([Cl:11])[cH:9]1.CS(=O)(=O)[Cl:8]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][Cl:8])[cH:9][c:10]1[Cl:11] | COc1ccc(CO)cc1Cl.CS(=O)(=O)Cl | COc1ccc(CCl)cc1Cl | null | null | O1CCCC1 | Functional Group Interconversion | Alcohol to chloride_sulfonyl chloride | 58d25ddf86b8daa38762ecb08ed922faa2d01716f69924f9b8413703fe1b3fc7 | d5d71bad4297b1f4f93dd1d1d9cddf0bb6fadb3f4dca1f84369c4074a39097d6 | c1ccccc1 | C-S(=O)(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 61.1 | [{"value": 61.0, "product": "ClC=1C=C(CCl)C=CC1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.1, "product": "ClC=1C=C(CCl)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of 3-chloro-4-methoxybenzyl alcohol (1.1 g, 6 mmol) in tetrahydrofuran (5 mL) were added under ice-cooling triethylamine (1.67 mL, 12 mmol) and methanesulfonyl chloride (0.51 ml, 6 mmol) and the mixture was stirred at room temperature for 18 h. The solvent was evaporated under reduced pressure and the obt... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Primary halide | null | null | c1ccccc1 | HO- | O1CCCC1 | null | 18 | COc1ccc(CO)cc1Cl.CS(=O)(=O)Cl>O1CCCC1>COc1ccc(CCl)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-731e44cf7bd248f291c99babee57228d | COc1ccc(C=O)cc1F>>COc1ccc(CO)cc1F | FC=1C=C(C=O)C=CC1OC.[BH4-].[Na+]>>FC=1C=C(CO)C=CC1OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[cH:9][c:10]1[F:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:9][c:10]1[F:11] | COc1ccc(C=O)cc1F | COc1ccc(CO)cc1F | null | null | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 100 | [{"value": 100.0, "product": "FC=1C=C(CO)C=CC1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.5, "product": "FC=1C=C(CO)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3-fluoro-4-methoxybenzaldehyde (1 g, 6.5 mmol) in methanol (15 mL) was added under ice-cooling sodium borohydride (378 mg, 10 mmol) and the mixture was stirred at room temperature for 1 h. The solvent was evaporated under reduced pressure and the obtained residue was dissolved in ethyl acetate. The org... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1 | null | CO | null | 1 | COc1ccc(C=O)cc1F>CO>COc1ccc(CO)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c80cfa37516948f992096c6023c594af | COc1ccc(CO)cc1F.CS(=O)(=O)Cl>>COc1ccc(CCl)cc1F | FC=1C=C(CO)C=CC1OC.C(C)N(CC)CC.CS(=O)(=O)Cl>>FC=1C=C(CCl)C=CC1OC | O[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:10]([F:11])[cH:9]1.CS(=O)(=O)[Cl:8]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][Cl:8])[cH:9][c:10]1[F:11] | COc1ccc(CO)cc1F.CS(=O)(=O)Cl | COc1ccc(CCl)cc1F | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_sulfonyl chloride | 58d25ddf86b8daa38762ecb08ed922faa2d01716f69924f9b8413703fe1b3fc7 | d5d71bad4297b1f4f93dd1d1d9cddf0bb6fadb3f4dca1f84369c4074a39097d6 | c1ccccc1 | C-S(=O)(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 100 | [{"value": 100.0, "product": "FC=1C=C(CCl)C=CC1OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.9, "product": "FC=1C=C(CCl)C=CC1OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 3-fluoro-4-methoxybenzyl alcohol (1 g, 6.5 mmol) in dichloromethane (10 mL) were added under ice-cooling triethylamine (1.8 mL, 13 mmol) and methanesulfonyl chloride (0.60 mL, 7 mmol) and the mixture was stirred at room temperature for 30 min. The solvent was evaporated under reduced pressure and the o... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Primary halide | null | null | c1ccccc1 | HO- | ClCCl | null | 0.5 | COc1ccc(CO)cc1F.CS(=O)(=O)Cl>ClCCl>COc1ccc(CCl)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c167f9a9f1b44cc9678a067bdab38e6 | CI.O=Cc1ccc(O)cc1Cl>>COc1ccc(C=O)c(Cl)c1 | O.ClC1=C(C=O)C=CC(=C1)O.C([O-])([O-])=O.[K+].[K+].CI>>ClC1=C(C=O)C=CC(=C1)OC | I[CH3:1].[OH:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9]([Cl:10])[cH:11]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9]([Cl:10])[cH:11]1 | CI.O=Cc1ccc(O)cc1Cl | COc1ccc(C=O)c(Cl)c1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b8b041187bac58376aae824630608e7deb49a01db3d652291f8b379c10d4e434 | 0f0966e3597a58033417ecee71659f4d0c082f95d46b1e52c95541e6e4a59086 | c1ccccc1 | I-[CH3;D1;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | 71 | [{"value": 70.0, "product": "ClC1=C(C=O)C=CC(=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.0, "product": "ClC1=C(C=O)C=CC(=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of 2-chloro-4-hydroxybenzaldehyde (2 g, 12.8 mmol) in N,N-dimethylformamide (25 mL) were added potassium carbonate (3.46 g, 25 mmol) and methyl iodide (large excess) and the mixture was stirred at room temperature for 18 h. Water was added to the reaction mixture and the mixture was extracted with ethyl a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Ether | null | null | c1ccccc1 | HI | CN(C=O)C | null | 18 | CI.O=Cc1ccc(O)cc1Cl>CN(C=O)C>COc1ccc(C=O)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8f16daff33a54d7dbea2b1c031fe1318 | COc1ccc(C=O)c(Cl)c1>>COc1ccc(CO)c(Cl)c1 | ClC1=C(C=O)C=CC(=C1)OC.[BH4-].[Na+]>>ClC1=C(CO)C=CC(=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9]([Cl:10])[cH:11]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[c:9]([Cl:10])[cH:11]1 | COc1ccc(C=O)c(Cl)c1 | COc1ccc(CO)c(Cl)c1 | null | null | CO | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | c1ccccc1 | [O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 97 | [{"value": 97.0, "product": "ClC1=C(CO)C=CC(=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.6, "product": "ClC1=C(CO)C=CC(=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 2-chloro-4-methoxybenzaldehyde (1.55 g, 9 mmol) in methanol (20 mL) was added under ice-cooling sodium borohydride (378 mg, 10 mmol) and the mixture was stirred at room temperature for 30 min. The solvent was evaporated under reduced pressure and the obtained residue was dissolved in ethyl acetate. The... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1 | null | CO | null | 0.5 | COc1ccc(C=O)c(Cl)c1>CO>COc1ccc(CO)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b00621e1ea214c459e6cb56650daa47b | COc1ccc(CO)c(Cl)c1.CS(=O)(=O)Cl>>COc1ccc(CCl)c(Cl)c1 | ClC1=C(CO)C=CC(=C1)OC.C(C)N(CC)CC.CS(=O)(=O)Cl>>ClC1=C(CCl)C=CC(=C1)OC | O[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:11][c:9]1[Cl:10].CS(=O)(=O)[Cl:8]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][Cl:8])[c:9]([Cl:10])[cH:11]1 | COc1ccc(CO)c(Cl)c1.CS(=O)(=O)Cl | COc1ccc(CCl)c(Cl)c1 | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_sulfonyl chloride | 58d25ddf86b8daa38762ecb08ed922faa2d01716f69924f9b8413703fe1b3fc7 | d5d71bad4297b1f4f93dd1d1d9cddf0bb6fadb3f4dca1f84369c4074a39097d6 | c1ccccc1 | C-S(=O)(=O)-[Cl;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 61 | [{"value": 61.0, "product": "ClC1=C(CCl)C=CC(=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.8, "product": "ClC1=C(CCl)C=CC(=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 2-chloro-4-methoxybenzyl alcohol (1.5 g, 8.7 mmol) in dichloromethane (10 mL) were added under ice-cooling triethylamine (2.4 mL, 17.4 mmol) and methanesulfonyl chloride (0.74 mL, 9.5 mmol) and the mixture was stirred at room temperature for 2 h. The solvent was evaporated under reduced pressure and th... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Primary halide | null | null | c1ccccc1 | HO- | ClCCl | null | 2 | COc1ccc(CO)c(Cl)c1.CS(=O)(=O)Cl>ClCCl>COc1ccc(CCl)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9d6f264348c148c5921ef355a3645ed6 | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1O.CCOC(=O)c1cnc(N2c3ccccc3C[C@H]2C)nc1O>>CCOC(=O)c1cnc(N2c3ccccc3C[C@H]2C)nc1OC(C)c1ccccc1 | OC1=NC(=NC=C1C(=O)OCC)N1CCC2=CC=CC=C12.OC1=NC(=NC=C1C(=O)OCC)N1[C@@H](CC2=CC=CC=C12)C>>C[C@H]1N(C2=CC=CC=C2C1)C1=NC=C(C(=N1)OC(C)C1=CC=CC=C1)C(=O)OCC | CCOC(=O)c1cnc(N2[CH2:24][CH2:23][c:25]3[cH:26][cH:27][cH:28][cH:29][c:30]32)nc1O.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([N:10]2[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[CH2:17][C@H:18]2[CH3:19])[n:20][c:21]1[OH:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]([N:10]2[c:11]3[cH:12][cH:13][cH:... | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1O.CCOC(=O)c1cnc(N2c3ccccc3C[C@H]2C)nc1O | CCOC(=O)c1cnc(N2c3ccccc3C[C@H]2C)nc1OC(C)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2724f80c2567a4f114f4a243ee529f50ccfc2f75653a37ba7ef63b9c8def247e | 3d147d59f10970b97131a934c589965ca51508f13649cb58509581dd98eb4186 | c1ccc(COc2ccnc(N3CCc4ccccc43)n2)cc1 | C-C-O-C(=O)-c1:c:n:c(-N2-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c;H0;D3;+0:5]-2:[c:6]:[c:7]):n:c:1-O.[#8:8]-[C:9](=[O;D1;H0:10])-[c:11]1:[c:12]:[#7;a:13]:[c:14]:[#7;a:15]:[c:16]:1-[OH;D1;+0:17]>>[#8:8]-[C:9](=[O;D1;H0:10])-[c:11]1:[c:12]:[#7;a:13]:[c:14]:[#7;a:15]:[c:16]:1-[O;H0;D2;+0:17]-[CH;D3;+0:2](-[CH3;D1;+0:1... | null | [] | null | null | null | null | In the same manner as in Reference Example 3-1 using ethyl 4-hydroxy-2-(2,3-dihydro-1H-indol-1-yl)-5-pyrimidinecarboxylate and ethyl 4-hydroxy-2-[(R)-2-methyl-2,3-dihydro-1H-indol-1-yl]-5-pyrimidinecarboxylate as starting materials, compounds of Reference Examples 26 and 27 were synthesized.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aromatic alcohol.Aromatic alcohol.Tertiary amine | Ether | c1cncnc1.c1ccc2c(c1)CCN2 | c1ccccc1 | c1cncnc1.c1ccc2c(c1)CC[NH]2.c1ccccc1 | HO- | null | null | null | CCOC(=O)c1cnc(N2CCc3ccccc32)nc1O.CCOC(=O)c1cnc(N2c3ccccc3C[C@H]2C)nc1O>>CCOC(=O)c1cnc(N2c3ccccc3C[C@H]2C)nc1OC(C)c1ccccc1 |
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