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-dd260658769041a1a6db30df808d65ab | COC(=O)c1ccc(C=C[N+](=O)[O-])cc1>>COC(=O)c1ccc(CCN)cc1 | COC(C1=CC=C(C=C1)C=C[N+](=O)[O-])=O.[H][H].[H][H]>>COC(C1=CC=C(C=C1)CCN)=O | O=[N+:11]([O-])[CH:10]=[CH:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:13][cH:12]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][CH2:10][NH2:11])[cH:12][cH:13]1 | COC(=O)c1ccc(C=C[N+](=O)[O-])cc1 | COC(=O)c1ccc(CCN)cc1 | null | [Pd] | C(C)(=O)O.C(C)O | Reduction | OtherReaction | 4337e4e8b75c4193a30be38c3139251eb50201a1e90dac1ecfc293dd3e226a46 | 1ad3bfd18d4cba7c52a6c2c4705cfa4e2dc99589d9555154a809489f21a7a436 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[CH;D2;+0:2]=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6] | 103.9 | [{"value": 103.9, "product": "COC(C1=CC=C(C=C1)CCN)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Palladium on carbon (10%, 50 mg) was added to a solution of 4-(2-nitrovinyl)benzoic acid methyl ester (228 mg) in 5 mL of ethyl alcohol and 2 mL of acetic acid. The reaction vessel was saturated with hydrogen and stirred under a 1 atm hydrogen atmosphere for 20 h. The vessel was saturated with nitrogen and filtered thr... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)(=O)O.C(C)O | null | null | COC(=O)c1ccc(C=C[N+](=O)[O-])cc1>[Pd].C(C)(=O)O.C(C)O>COC(=O)c1ccc(CCN)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6430fc8d554d40e2b51cd9ef7a03c206 | Cc1cc(C=C[N+](=O)[O-])cc(C)c1O[Si](C)(C)C(C)(C)C>>Cc1cc(CCN)cc(C)c1O[Si](C)(C)C(C)(C)C | C(C)(C)(C)[Si](C)(C)OC1=C(C=C(C=C1C)C=C[N+](=O)[O-])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[Si](C)(C)(C(C)(C)C)OC1=C(C=C(C=C1C)CCN)C | O=[N+:7]([O-])[CH:6]=[CH:5][c:4]1[cH:3][c:2]([CH3:1])[c:11]([O:12][Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19])[c:9]([CH3:10])[cH:8]1>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][CH2:6][NH2:7])[cH:8][c:9]([CH3:10])[c:11]1[O:12][Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19] | Cc1cc(C=C[N+](=O)[O-])cc(C)c1O[Si](C)(C)C(C)(C)C | Cc1cc(CCN)cc(C)c1O[Si](C)(C)C(C)(C)C | null | null | C(C)OCC | Reduction | OtherReaction | 4337e4e8b75c4193a30be38c3139251eb50201a1e90dac1ecfc293dd3e226a46 | 1ad3bfd18d4cba7c52a6c2c4705cfa4e2dc99589d9555154a809489f21a7a436 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[CH;D2;+0:2]=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[c:4](:[c:5]):[c:6] | 55 | [{"value": 55.0, "product": "[Si](C)(C)(C(C)(C)C)OC1=C(C=C(C=C1C)CCN)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | A solution of tert-butyl-[2,6-dimethyl-4-(2-nitrovinyl)phenoxy]dimethylsilane (0.20 g) in 15 mL diethyl ether was cooled to 0° C. Lithium aluminum hydride (0.20 g) was added in portions to the stirring nitroalkene solution. The resulting slurry was refluxed for 3 h and then cooled to 0° C. The mixture is carefully quen... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Primary amine | null | null | c1ccccc1 | Other | C(C)OCC | 0 | 0.25 | Cc1cc(C=C[N+](=O)[O-])cc(C)c1O[Si](C)(C)C(C)(C)C>C(C)OCC>Cc1cc(CCN)cc(C)c1O[Si](C)(C)C(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-05979e650a604461bc29aa3be1d9d2c3 | NCc1ccc(C(=O)O)cc1>>NCc1ccc(CO)cc1 | NCC1=CC=C(C(=O)O)C=C1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>NCC1=CC=C(C=C1)CO | O=[C:7]([c:6]1[cH:5][cH:4][c:3]([CH2:2][NH2:1])[cH:10][cH:9]1)[OH:8]>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:9][cH:10]1 | NCc1ccc(C(=O)O)cc1 | NCc1ccc(CO)cc1 | null | null | C(C)OCC | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccccc1 | 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] | 82.6 | [{"value": 82.6, "product": "NCC1=CC=C(C=C1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | A solution of 4-aminomethyl-benzoic acid (0.20 g) in 20 mL diethyl ether was cooled to 0° C. Lithium aluminum hydride (0.19 g) was added in portions to the stirring carboxylic acid solution. The resulting slurry was stirred for 20 h and then cooled to 0 C. The mixture was carefully quenched by the sequential addition o... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1 | Other | C(C)OCC | null | 20 | NCc1ccc(C(=O)O)cc1>C(C)OCC>NCc1ccc(CO)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-443e59999fd64eac976cc8d305d90497 | COc1ccc2c(c1)CCCC(OC)(OC)C2>>COc1ccc2c(c1)CCCC(=O)C2 | COC=1C=CC2=C(CCCC(C2)(OC)OC)C1.O.C1(=CC=C(C=C1)S(=O)(=O)O)C.CC(=O)C>>COC=1C=CC2=C(CCCC(C2)=O)C1 | CO[C:12]1([O:13]C)[CH2:11][CH2:10][CH2:9][c:7]2[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]2)[CH2:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH2:11][C:12](=[O:13])[CH2:14]2 | COc1ccc2c(c1)CCCC(OC)(OC)C2 | COc1ccc2c(c1)CCCC(=O)C2 | null | null | ClCCl.O.C(O)([O-])=O.[Na+] | Miscellaneous | Ketal hydrolysis to ketone | f78aada599ca643af43e8e424ed4099b5663efd62ba1db7cf970a2d69a85f55e | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1CCCc2ccccc2C1 | C-O-[C;H0;D4;+0:1](-[O;H0;D2;+0:2]-C)(-[C:3]-[C:4])-[C:5]-[c:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:5]-[c:6] | 80.2 | [{"value": 80.2, "product": "COC=1C=CC2=C(CCCC(C2)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2,6,6-trimethoxy-6,7,8,9-tetrahydro-5H-benzocycloheptene (387 mg) and p-toluenesulfonic acid monohydrate (31 mg) was stirred in 5 mL of 1:1 water:acetone. The mixture was diluted with 50 mL of dichloromethane and 50 mL of saturated sodium hydrogen carbonate. The aqueous layer was re-extracted with 50 mL m... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | c1ccc2c(c1)CCCCC2 | c1ccc2c(c1)CCCCC2 | c1ccc2c(c1)CCCCC2 | HO- | ClCCl.O.C(O)([O-])=O.[Na+] | null | null | COc1ccc2c(c1)CCCC(OC)(OC)C2>ClCCl.O.C(O)([O-])=O.[Na+]>COc1ccc2c(c1)CCCC(=O)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cf21a2c6a3124730980c313880a02012 | CCOC(=O)C=Cc1ccc(OC)cc1.C[N+](=O)[O-]>>CCOC(=O)CC(C[N+](=O)[O-])c1ccc(OC)cc1 | C(C)OC(C=CC1=CC=C(C=C1)OC)=O.CN(C(N(C)C)=N)C.[N+](=O)([O-])C>>C(C)OC(CC(C[N+](=O)[O-])C1=CC=C(C=C1)OC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[CH:7][c:12]1[cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18][cH:19]1.[CH3:8][N+:9](=[O:10])[O-:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]([CH2:8][N+:9](=[O:10])[O-:11])[c:12]1[cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18][cH:19]1 | CCOC(=O)C=Cc1ccc(OC)cc1.C[N+](=O)[O-] | CCOC(=O)CC(C[N+](=O)[O-])c1ccc(OC)cc1 | null | null | null | C-C Coupling | Michael addition methyl | 50ea1c0ba058ccacb15ab052551689abf7203df0eb57f759b19d338f06631649 | 6f872e1e6593abcdd0d9fb5775fd31c259676a11a338f4f9b2b3594108a0aabd | c1ccccc1 | [CH3;D1;+0:1]-[#7;+:2](-[O;-;D1;H0:3])=[O;D1;H0:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D2;+0:9]=[CH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[CH;D3;+0:10](-[CH2;D2;+0:1]-[#7;+:2](-[O;-;D1;H0:3])=[O;D1;H0:4])-[c:11](:[c:12]):[c:13] | null | [] | null | null | null | null | A solution of 3-(4-methoxy-phenyl)acrylic acid ethyl ester (1.0 g) and tetramethyl-guanidine (125 μL) was stirred for 24 h at 70° C. in 2.5 mL nitromethane. The solvent was evaporated and the resulting residue was partitioned in 50 mL 1 N hydrochloric acid and 50 mL ethyl ether. The ethyl ether phase was collected and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitro group | Ester.Nitro group | null | null | c1ccccc1 | null | null | null | null | CCOC(=O)C=Cc1ccc(OC)cc1.C[N+](=O)[O-]>>CCOC(=O)CC(C[N+](=O)[O-])c1ccc(OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-51057ba33ac843df960a60de27fd9d4c | N#Cc1c[nH]c2ccccc12>>NCc1c[nH]c2ccccc12 | [H-].[Al+3].[Li+].[H-].[H-].[H-].N1C=C(C2=CC=CC=C12)C#N.O1CCCC1>>N1C=C(C2=CC=CC=C12)CN | [N:1]#[C:2][c:3]1[cH:4][nH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]12>>[NH2:1][CH2:2][c:3]1[cH:4][nH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]12 | N#Cc1c[nH]c2ccccc12 | NCc1c[nH]c2ccccc12 | null | null | O1CCOCC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc2[nH]ccc2c1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:1 | 54.5 | [{"value": 54.5, "product": "N1C=C(C2=CC=CC=C12)CN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | Lithium aluminum hydride (100 mg) was added to a solution of 1H-indole-3-carbonitrile (100 mg) in 15 mL of 2:1 dioxane:tetrahydrofuran. The mixture was refluxed for 0.5 h, then cooled to 0 C and quenched by the sequential addition of 0.1 mL water, 0.1 mL 3 N sodium hydroxide, and 0.3 mL more water. After the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccc2[nH]ccc2c1 | null | O1CCOCC1 | null | 0.25 | N#Cc1c[nH]c2ccccc12>O1CCOCC1>NCc1c[nH]c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e5c557f7a27d4624a1960146dfa584ae | COc1ccc2c(CCN)c[nH]c2c1>>NCCc1c[nH]c2cc(O)ccc12 | [H-].C(C(C)C)[Al+]CC(C)C.COC1=CC=C2C(=CNC2=C1)CCN>>NCCC1=CNC2=CC(=CC=C12)O | C[O:10][c:9]1[cH:8][c:7]2[nH:6][cH:5][c:4]([CH2:3][CH2:2][NH2:1])[c:13]2[cH:12][cH:11]1>>[NH2:1][CH2:2][CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][c:9]([OH:10])[cH:11][cH:12][c:13]12 | COc1ccc2c(CCN)c[nH]c2c1 | NCCc1c[nH]c2cc(O)ccc12 | null | null | C1(=CC=CC=C1)C | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2[nH]ccc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 68.2 | [{"value": 68.2, "product": "NCCC1=CNC2=CC(=CC=C12)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | Diisobutylaluminum hydride (1 M in toluene, 15 mL) was slowly added to a suspension of 2-(6-methoxy-1H-indol-3-yl)ethylamine (250 mg) in 20 mL of toluene. The resulting clear solution was refluxed for 10 h, then cooled to 0° C. and quenched by the careful addition of 20 mL of 1:1 methyl alcohol:water. The mixture was s... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2[nH]ccc2c1 | Other | C1(=CC=CC=C1)C | 0 | 0.25 | COc1ccc2c(CCN)c[nH]c2c1>C1(=CC=CC=C1)C>NCCc1c[nH]c2cc(O)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-94519c87f60641e69754c5d68bb615e7 | C=O.NCCc1c[nH]c2ccc(O)cc12>>Oc1ccc2[nH]c3c(c2c1)CCNC3 | Cl.NCCC1=CNC2=CC=C(C=C12)O.C=O.C(C)(=O)O>>Cl.C1NCCC=2C3=CC(=CC=C3NC12)O | O=[CH2:15].[OH:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][cH:8][c:9]([CH2:12][CH2:13][NH2:14])[c:10]2[cH:11]1>>[OH:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[c:9]([c:10]2[cH:11]1)[CH2:12][CH2:13][NH:14][CH2:15]3 | C=O.NCCc1c[nH]c2ccc(O)cc12 | Oc1ccc2[nH]c3c(c2c1)CCNC3 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 9266c73c6bd92c1e1d5661d1c7ea0b602764aa1f6f11776c4b52067dc1538fcc | cf32f1267c674fd84d46b8a676a46bd4e3a018dea282d34ea9ab93d79b66d0ee | c1ccc2c3c([nH]c2c1)CNCC3 | O=[CH2;D1;+0:1].[NH2;D1;+0:2]-[C:3]-[C:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[cH;D2;+0:9]:1>>[#7;a:8]1:[c:7]:[c:6]:[c:5]2:[c;H0;D3;+0:9]:1-[CH2;D2;+0:1]-[NH;D2;+0:2]-[C:3]-[C:4]-2 | null | [] | null | null | null | null | To a solution of 3-(2-amino-ethyl)-1H-indol-5-ol hydrochloride (10.0 g) in 450 mL of absolute ethanol was added 1.6 g of paraformaldehyde and 5.4 mL of glacial acetic acid. The mixture was heated to reflux for 1.5 h then allowed to cool to rt. The white precipitate so formed was collected by filtration and dried under ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Secondary amine | c1ccc2[nH]ccc2c1 | c1ccc2c3c([nH]c2c1)CNCC3 | c1ccc2c3c([nH]c2c1)CNCC3 | HO- | C(C)O | null | null | C=O.NCCc1c[nH]c2ccc(O)cc12>C(C)O>Oc1ccc2[nH]c3c(c2c1)CCNC3 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ec54e13d81204fff901de7e6692aa8ad | NCCc1c[nH]c2ccc(O)cc12>>Oc1ccc2[nH]c3c(c2c1)CCNC3 | C(C)(=O)O.Cl.NCCC1=CNC2=CC=C(C=C12)O.C(C)=O>>C1NCCC=2C3=CC(=CC=C3NC12)O | [OH:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][cH:7][c:8]([CH2:11][CH2:12][NH2:13])[c:9]2[cH:10]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][c:7]3[c:8]([c:9]2[cH:10]1)[CH2:11][CH2:12][NH:13][CH2:14]3 | NCCc1c[nH]c2ccc(O)cc12 | Oc1ccc2[nH]c3c(c2c1)CCNC3 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | a264c9fddf76d4982cd14c054d97cbca1d44d9dd749e612ca0954da9145f0b03 | c6874c6af41d3b1c4f7668e1cd342c90252d0e77f4317d31b3193ebc2f9501a3 | c1ccc2c3c([nH]c2c1)CNCC3 | [NH2;D1;+0:1]-[C:2]-[C:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[cH;D2;+0:8]:1>>[#7;a:7]1:[c:6]:[c:5]:[c:4]2:[c;H0;D3;+0:8]:1-[C:9]-[NH;D2;+0:1]-[C:2]-[C:3]-2 | null | [] | 75 | CELSIUS | null | null | Acetic acid was added dropwise to a solution of 3-(2-amino-ethyl)-1H-indol-5-ol hydrochloride (200 mg) in 7 mL of methanol until the pH=4. Acetaldehyde (0.2 mL) was added and the mixture was heated at 75° C. in a sealed tube for 1 h. The tube was cooled to rt and unsealed. The solvent was evaporated yielding 160 mg of ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amine | c1ccc2[nH]ccc2c1 | c1ccc2c3c([nH]c2c1)CNCC3 | c1ccc2c3c([nH]c2c1)CNCC3 | Other | CO | 75 | null | NCCc1c[nH]c2ccc(O)cc12>CO>Oc1ccc2[nH]c3c(c2c1)CCNC3 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-600460d8babf4f8aadae29babece78a3 | CCOC(O)C(F)(F)F.NCCc1c[nH]c2ccc(O)cc12>>Oc1ccc2[nH]c3c(c2c1)CCNC3C(F)(F)F | Cl.NCCC1=CNC2=CC=C(C=C12)O.C(C)OC(C(F)(F)F)O.C(C)(=O)O>>Cl.FC(C1NCCC=2C3=CC(=CC=C3NC12)O)(F)F | CCO[CH:15](O)[C:16]([F:17])([F:18])[F:19].[OH:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][cH:8][c:9]([CH2:12][CH2:13][NH2:14])[c:10]2[cH:11]1>>[OH:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[c:9]([c:10]2[cH:11]1)[CH2:12][CH2:13][NH:14][CH:15]3[C:16]([F:17])([F:18])[F:19] | CCOC(O)C(F)(F)F.NCCc1c[nH]c2ccc(O)cc12 | Oc1ccc2[nH]c3c(c2c1)CCNC3C(F)(F)F | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | d5e69fdbb75f492eba4c0dbc1df53acfa69cf46b73abd788fa90dbc8af280801 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | c1ccc2c3c([nH]c2c1)CNCC3 | C-C-O-[CH;D3;+0:1](-O)-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[F;D1;H0:5].[NH2;D1;+0:6]-[C:7]-[C:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[cH;D2;+0:13]:1>>[F;D1;H0:3]-[C:2](-[F;D1;H0:4])(-[F;D1;H0:5])-[CH;D3;+0:1]1-[NH;D2;+0:6]-[C:7]-[C:8]-[c:9]2:[c:10]:[c:11]:[#7;a:12]:[c;H0;D3;+0:13]:2-1 | null | [] | null | null | null | null | A mixture of 3-(2-amino-ethyl)-1H-indol-5-ol hydrochloride (0.5 g), trifluoroacetaldehyde ethyl hemiacetal (0.35 mL), acetic acid (0.32 mL) and ethanol (22.5 mL) was heated at reflux for 16 h. The solvent and excess reagents were evaporated to dryness under vacuum. The residue was washed with diethyl ether to afford 1-... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary alcohol.Primary amine | Secondary amine | c1ccc2[nH]ccc2c1 | c1ccc2c3c([nH]c2c1)CNCC3 | c1ccc2c3c([nH]c2c1)CNCC3 | HO- | C(C)O | null | null | CCOC(O)C(F)(F)F.NCCc1c[nH]c2ccc(O)cc12>C(C)O>Oc1ccc2[nH]c3c(c2c1)CCNC3C(F)(F)F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1f048dede2bf4d0c8393ab8fe5ff7f6b | NCCc1c[nH]c2ccc(O)cc12>>Oc1ccc2[nH]c3c(c2c1)CCNC3 | C(C)(=O)O.Cl.NCCC1=CNC2=CC=C(C=C12)O.C(CC)=O>>C1NCCC=2C3=CC(=CC=C3NC12)O | [OH:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][cH:7][c:8]([CH2:11][CH2:12][NH2:13])[c:9]2[cH:10]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][c:7]3[c:8]([c:9]2[cH:10]1)[CH2:11][CH2:12][NH:13][CH2:14]3 | NCCc1c[nH]c2ccc(O)cc12 | Oc1ccc2[nH]c3c(c2c1)CCNC3 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | a264c9fddf76d4982cd14c054d97cbca1d44d9dd749e612ca0954da9145f0b03 | c6874c6af41d3b1c4f7668e1cd342c90252d0e77f4317d31b3193ebc2f9501a3 | c1ccc2c3c([nH]c2c1)CNCC3 | [NH2;D1;+0:1]-[C:2]-[C:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[cH;D2;+0:8]:1>>[#7;a:7]1:[c:6]:[c:5]:[c:4]2:[c;H0;D3;+0:8]:1-[C:9]-[NH;D2;+0:1]-[C:2]-[C:3]-2 | null | [] | 75 | CELSIUS | null | null | Acetic acid was added dropwise to a solution of 3-(2-amino-ethyl)-1H-indol-5-ol hydrochloride (200 mg) in 7 mL methanol until the pH=4. Propionaldehyde (0.2 mL) was added and the mixture was heated at 75° C. in a sealed tube for 1 h. The tube was cooled to rt and unsealed. The solvent was evaporated to yield 190 mg of ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amine | c1ccc2[nH]ccc2c1 | c1ccc2c3c([nH]c2c1)CNCC3 | c1ccc2c3c([nH]c2c1)CNCC3 | Other | CO | 75 | null | NCCc1c[nH]c2ccc(O)cc12>CO>Oc1ccc2[nH]c3c(c2c1)CCNC3 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-068e324f42144e96b9bab928625a14ad | COc1ccc([N+](=O)[O-])c(C)c1C>>COc1ccc2[nH]ccc2c1C | COC1=C(C(=C(C=C1)[N+](=O)[O-])C)C.COC(N(C)C)OC.C(C)N(CC)CC>>COC=1C(=C2C=CNC2=CC1)C | O=[N+:7]([O-])[c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:11]([CH3:12])[c:10]1[CH3:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][cH:8][cH:9][c:10]2[c:11]1[CH3:12] | COc1ccc([N+](=O)[O-])c(C)c1C | COc1ccc2[nH]ccc2c1C | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 557c60b8cea2f6249621605faa3355a7b28bb1f25c8d4d5ec9f8266b943c90e8 | 899ebca2d6bba86d6be0360dea40833668d6eca1204c0c9fa1f9358f23c9856e | c1ccc2[nH]ccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](-[CH3;D1;+0:5]):[c:6]>>[c:6]:[c:4]1:[cH;D2;+0:5]:[c:7]:[nH;D2;+0:1]:[c:2]:1:[c:3] | null | [] | null | null | 40 | MINUTE | A solution of 1-methoxy-2,3-dimethyl-4-nitro-benzene (5.0 g), N,N-dimethylformamide dimethylacetal (7.4 mL) and triethylamine (0.10 mL) in 25 mL of N,N-dimethylformamide was heated to reflux for 3 days under nitrogen. The volatiles were removed in vacuo and the resulting residue was dissolved in 40 mL of a 1:1 mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | null | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | Other | CN(C=O)C | null | 0.666667 | COc1ccc([N+](=O)[O-])c(C)c1C>CN(C=O)C>COc1ccc2[nH]ccc2c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cb0d67a099774221b16872d3e7d1a7ba | C=O.CNC.COc1ccc2[nH]ccc2c1C>>COc1ccc2[nH]cc(CN(C)C)c2c1C | C(C)(=O)O.CNC.C=O.COC=1C(=C2C=CNC2=CC1)C>>COC=1C(=C2C(=CNC2=CC1)CN(C)C)C | O=[CH2:13].[CH3:10][NH:11][CH3:12].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][cH:8][cH:9][c:14]2[c:15]1[CH3:16]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][cH:8][c:9]([CH2:10][N:11]([CH3:12])[CH3:13])[c:14]2[c:15]1[CH3:16] | C=O.CNC.COc1ccc2[nH]ccc2c1C | COc1ccc2[nH]cc(CN(C)C)c2c1C | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 14f2bfa3d907d463fab4dfc74293051dd668edd77fb6e0a45ccb47b35b91e990 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc2[nH]ccc2c1 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[NH;D2;+0:3]-[CH3;D1;+0:4].[c:5]:[c:6]1:[cH;D2;+0:7]:[c:8]:[#7;a:9]:[c:10]:1:[c:11]>>[C;D1;H3:2]-[N;H0;D3;+0:3](-[CH3;D1;+0:1])-[CH2;D2;+0:4]-[c;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[c:10](:[c:11]):[c:6]:1:[c:5] | null | [] | null | null | null | null | Acetic acid (0.39 mL) and dimethylamine (0.85 mL of a 40% aqueous solution) were added to a suspension of paraformaldehyde (0.21 g) in 25 mL ethanol. The mixture was heated to reflux until it was clear. The solution was cooled to rt and a solution of 5-methoxy-4-methyl-indole (1.0 g) in 25 mL of ethanol was added. The ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HO- | C(C)O | null | null | C=O.CNC.COc1ccc2[nH]ccc2c1C>C(C)O>COc1ccc2[nH]cc(CN(C)C)c2c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-72abe992e3ec45f2ad4431dc0d535d8d | COc1ccc2[nH]cc(CN(C)C)c2c1C.[C-]#N>>COc1ccc2[nH]cc(CC#N)c2c1C | [C-]#N.[K+].COC=1C(=C2C(=CNC2=CC1)CN(C)C)C>>COC=1C(=C2C(=CNC2=CC1)CC#N)C | CN(C)[CH2:10][c:9]1[cH:8][nH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:14]([CH3:15])[c:13]21.[C-:11]#[N:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][cH:8][c:9]([CH2:10][C:11]#[N:12])[c:13]2[c:14]1[CH3:15] | COc1ccc2[nH]cc(CN(C)C)c2c1C.[C-]#N | COc1ccc2[nH]cc(CC#N)c2c1C | null | null | O.CN(C=O)C | C-C Coupling | OtherReaction | 7c3cd4186d11953ea4e0b19a62fb50025f0b4718c21bc068a8f6361abc377dd4 | 5c74fd47885e128c4d459160e2b8f8075dc2f828c14f4443adde337b21dd6416 | c1ccc2[nH]ccc2c1 | C-N(-C)-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C-;H0;D1:7]#[N;D1;H0:8]>>[N;D1;H0:8]#[C;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 87.2 | [{"value": 87.2, "product": "COC=1C(=C2C(=CNC2=CC1)CC#N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of potassium cyanide (0.74 g) in 20 mL water was added a solution of (5-methoxy-4-methyl-1H-indol-3-ylmethyl)dimethylamine (0.5 g) in 20 mL of N,N-dimethylformamide. The solution was heated to reflux for 40 min, cooled to rt, and 40 mL of ice water was added. The aqueous layer was extracted with three por... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Nitrile | null | null | c1ccc2[nH]ccc2c1 | Other | O.CN(C=O)C | null | null | COc1ccc2[nH]cc(CN(C)C)c2c1C.[C-]#N>O.CN(C=O)C>COc1ccc2[nH]cc(CC#N)c2c1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5a7e3236c03546a79481668dbf1dafbb | CC(C)[Si](Cl)(C(C)C)C(C)C.NCCc1c[nH]c2ccc(O)cc12>>CC(C)[Si](Oc1ccc2[nH]cc(CCN)c2c1)(C(C)C)C(C)C | NCCC1=CNC2=CC=C(C=C12)O.N1C=NC=C1.C(C)(C)[Si](C(C)C)(C(C)C)Cl>>C(C)(C)[Si](OC=1C=C2C(=CNC2=CC1)CCN)(C(C)C)C(C)C | Cl[Si:4]([CH:2]([CH3:1])[CH3:3])([CH:18]([CH3:19])[CH3:20])[CH:21]([CH3:22])[CH3:23].[OH:5][c:6]1[cH:7][cH:8][c:9]2[nH:10][cH:11][c:12]([CH2:13][CH2:14][NH2:15])[c:16]2[cH:17]1>>[CH3:1][CH:2]([CH3:3])[Si:4]([O:5][c:6]1[cH:7][cH:8][c:9]2[nH:10][cH:11][c:12]([CH2:13][CH2:14][NH2:15])[c:16]2[cH:17]1)([CH:18]([CH3:19])[CH3... | CC(C)[Si](Cl)(C(C)C)C(C)C.NCCc1c[nH]c2ccc(O)cc12 | CC(C)[Si](Oc1ccc2[nH]cc(CCN)c2c1)(C(C)C)C(C)C | null | null | C(C)(=O)OCC.CN(C=O)C | Protection | Alcohol protection with silyl ethers | b0a79881d208ba0e98fadf827b99c8e154abae20183442d92687b20dcffdaf4c | d57b05ecffa00e68e6b49fce42d0b589b6267b94f85326e13293a0e3abd8a48b | c1ccc2[nH]ccc2c1 | Cl-[Si;H0;D4;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](-[C;D1;H3:9])-[C;D1;H3:10].[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])-[Si;H0;D4;+0:1](-[O;H0;D2;+0:11]-[c:12](:[c:13]):[c:14])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](-[C;D1;H3:9])-[C;D1;H3:10] | null | [] | null | null | null | null | A solution of 3-(2-amino-ethyl)-1H-indol-5-ol (3.0 g), imidazole (9.6 g), and triisopropylsilyl chloride (4.5 mL) was stirred in 20 mL N,N-dimethylformamide for 6 h. The solution was diluted with 100 mL of ethyl acetate and washed with 100 mL of sodium carbonate and 100 mL of saturated sodium chloride (3 times). The or... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | Silyl protective group | null | null | c1ccc2[nH]ccc2c1 | HCl | C(C)(=O)OCC.CN(C=O)C | null | null | CC(C)[Si](Cl)(C(C)C)C(C)C.NCCc1c[nH]c2ccc(O)cc12>C(C)(=O)OCC.CN(C=O)C>CC(C)[Si](Oc1ccc2[nH]cc(CCN)c2c1)(C(C)C)C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5ef23cd1e7d40e5b80f3c58363f7221 | CC(C)[Si](Oc1ccc2[nH]c3c(c2c1)CCN(C(=O)OC(C)(C)C)C3)(C(C)C)C(C)C.CI>>CC(C)[Si](Oc1ccc2c(c1)c1c(n2C)CN(C(=O)OC(C)(C)C)CC1)(C(C)C)C(C)C | IC.N1C=CC2=CC=CC=C12.C(C)(C)(C)OC(=O)N1CC=2NC3=CC=C(C=C3C2CC1)O[Si](C(C)C)(C(C)C)C(C)C.CC(C)([O-])C.[K+].C1COCCOCCOCCOCCOCCO1>>C(C)(C)(C)OC(=O)N1CC=2N(C3=CC=C(C=C3C2CC1)O[Si](C(C)C)(C(C)C)C(C)C)C | [CH3:1][CH:2]([CH3:3])[Si:4]([O:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[c:12]1[c:13]([nH:14]2)[CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]1)([CH:27]([CH3:28])[CH3:29])[CH:30]([CH3:31])[CH3:32].I[CH3:15]>>[CH3:1][CH:2]([CH3:3])[Si:4]([O:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:1... | CC(C)[Si](Oc1ccc2[nH]c3c(c2c1)CCN(C(=O)OC(C)(C)C)C3)(C(C)C)C(C)C.CI | CC(C)[Si](Oc1ccc2c(c1)c1c(n2C)CN(C(=O)OC(C)(C)C)CC1)(C(C)C)C(C)C | null | null | C(C)OCC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6bac1c67bf60d61953b9747b6c95faf1f808a374b9940a8973edc5ca13d75d23 | 7a358c636daddc97c1fb4c29f378044d7eac3f01815d9966e599841f642d631a | c1ccc2c3c([nH]c2c1)CNCC3 | I-[CH3;D1;+0:1].[#7:2]-[C:3]-[c:4]1:[c:5]:[c:6]:[c:7](:[c:8]):[nH;D2;+0:9]:1>>[#7:2]-[C:3]-[c:4]1:[c:5]:[c:6]:[c:7](:[c:8]):[n;H0;D3;+0:9]:1-[CH3;D1;+0:1] | 41.9 | [{"value": 41.9, "product": "C(C)(C)(C)OC(=O)N1CC=2N(C3=CC=C(C=C3C2CC1)O[Si](C(C)C)(C(C)C)C(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of 6-triisopropylsilanyloxy-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester (175 mg, 0.39 mmol) in 3 mL of ethyl ether was added to a vigorously stirring solution of potassium tert-butoxide (263 mg) and 18-crown-6 (16 mg) in 10 mL ethyl ether. After 10 min, iodomethane (73 uL) in 0.5 mL of ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c3c([nH]c2c1)C[NH]CC3 | c1ccc2[nH]c3c(c2c1)CCNC3 | c1ccc2[nH]c3c(c2c1)CCNC3 | HI | C(C)OCC | null | 0.166667 | CC(C)[Si](Oc1ccc2[nH]c3c(c2c1)CCN(C(=O)OC(C)(C)C)C3)(C(C)C)C(C)C.CI>C(C)OCC>CC(C)[Si](Oc1ccc2c(c1)c1c(n2C)CN(C(=O)OC(C)(C)C)CC1)(C(C)C)C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-635cce29b8b9494caf7fd86a177b023b | CC(C)[Si](Oc1ccc2c(c1)c1c(n2C)CN(C(=O)OC(C)(C)C)CC1)(C(C)C)C(C)C>>CC(C)[Si](Oc1ccc2c(c1)c1c(n2C)CNCC1)(C(C)C)C(C)C | C(C)(C)(C)OC(=O)N1CC=2N(C3=CC=C(C=C3C2CC1)O[Si](C(C)C)(C(C)C)C(C)C)C.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.CN1C2=CC=C(C=C2C=2CCNCC12)O[Si](C(C)C)(C(C)C)C(C)C | CC(C)(C)OC(=O)[N:17]1[CH2:16][c:13]2[c:12]([c:10]3[c:9]([cH:8][cH:7][c:6]([O:5][Si:4]([CH:2]([CH3:1])[CH3:3])([CH:20]([CH3:21])[CH3:22])[CH:23]([CH3:24])[CH3:25])[cH:11]3)[n:14]2[CH3:15])[CH2:19][CH2:18]1>>[CH3:1][CH:2]([CH3:3])[Si:4]([O:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[c:12]1[c:13]([n:14]2[CH3:15])[CH2:16][N... | CC(C)[Si](Oc1ccc2c(c1)c1c(n2C)CN(C(=O)OC(C)(C)C)CC1)(C(C)C)C(C)C | CC(C)[Si](Oc1ccc2c(c1)c1c(n2C)CNCC1)(C(C)C)C(C)C | null | null | ClCCl | Reduction | Boc amine deprotection | 4eea27ad39d12de8dd5d6a36d72a771aedfe3131a17bf914d9f1e564b91f016b | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc2c3c([nH]c2c1)CNCC3 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3]:[#7;a:4])-[C:5]-[C:6]>>[#7;a:4]:[c:3]-[C:2]-[NH;D2;+0:1]-[C:5]-[C:6] | null | [] | null | null | null | null | A solution of 9-methyl-6-triisopropylsilanyloxy-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester (175 mg) and 0.5 mL of trifluoroacetic acid in 3 mL dichloromethane was stirred for 4 h. The solvent was removed to afford 9-methyl-6-triisopropylsilanyloxy-2,3,4,9-tetrahydro-1H-β-carboline trifluoroacetat... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | c1ccc2nc3c(c2c1)CCNC3 | c1ccc2[nH]c3c(c2c1)CCNC3 | c1ccc2[nH]c3c(c2c1)CCNC3 | HO- | ClCCl | null | null | CC(C)[Si](Oc1ccc2c(c1)c1c(n2C)CN(C(=O)OC(C)(C)C)CC1)(C(C)C)C(C)C>ClCCl>CC(C)[Si](Oc1ccc2c(c1)c1c(n2C)CNCC1)(C(C)C)C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-acc4cf61188540a5b8199811016a6ac9 | C=C(C)[N+](=O)[O-].c1ccc(COc2ccc3[nH]ccc3c2)cc1>>CC(Cc1c[nH]c2ccc(OCc3ccccc3)cc12)[N+](=O)[O-] | C(C1=CC=CC=C1)OC=1C=C2C=CNC2=CC1.[N+](=O)([O-])C(=C)C>>C(C1=CC=CC=C1)OC=1C=C2C(=CNC2=CC1)CC(C)[N+](=O)[O-] | [CH3:1][C:2](=[CH2:3])[N+:21](=[O:22])[O-:23].[cH:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][c:20]12>>[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][c:20]12)[N+:21](=[O:22])[... | C=C(C)[N+](=O)[O-].c1ccc(COc2ccc3[nH]ccc3c2)cc1 | CC(Cc1c[nH]c2ccc(OCc3ccccc3)cc12)[N+](=O)[O-] | null | null | C1=CC=CC=C1 | C-C Coupling | Friedel-Crafts alkylation | afb2ffb7140546829340dde8c42a028fdc6d7228f80079fc6057f9ce4920725c | 62f7b8b1b06d8abe0a7458fcdb08bc1ff61c22493460bb08abd465e204dda1f5 | c1ccc(COc2ccc3[nH]ccc3c2)cc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](=[CH2;D1;+0:3])-[#7;+:4](-[O;-;D1;H0:5])=[O;D1;H0:6].[c:7]:[c:8]1:[cH;D2;+0:9]:[c:10]:[#7;a:11]:[c:12]:1:[c:13]>>[C;D1;H3:1]-[CH;D3;+0:2](-[CH2;D2;+0:3]-[c;H0;D3;+0:9]1:[c:10]:[#7;a:11]:[c:12](:[c:13]):[c:8]:1:[c:7])-[#7;+:4](-[O;-;D1;H0:5])=[O;D1;H0:6] | null | [] | null | null | null | null | To a stirred 0.5 M benzene solution of 5-benzyloxy-1H-indole (6 mL) was added 2-nitro-propene (5.2 mL of the 10% benzene solution). The reaction was heated at reflux under a nitrogen atmosphere overnight. The volatiles were removed and residue was purified by silica gel chromatography (20% EtOAc/hexanes) to afford 5-be... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Nitro group | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | null | C1=CC=CC=C1 | null | null | C=C(C)[N+](=O)[O-].c1ccc(COc2ccc3[nH]ccc3c2)cc1>C1=CC=CC=C1>CC(Cc1c[nH]c2ccc(OCc3ccccc3)cc12)[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c784588374a4ac3be3503b7507e6f15 | CC(Cc1c[nH]c2ccc(OCc3ccccc3)cc12)[N+](=O)[O-]>>CC(N)Cc1c[nH]c2ccc(OCc3ccccc3)cc12 | [H-].[Al+3].[Li+].[H-].[H-].[H-].C(C1=CC=CC=C1)OC=1C=C2C(=CNC2=CC1)CC(C)[N+](=O)[O-]>>C(C1=CC=CC=C1)OC=1C=C2C(=CNC2=CC1)CC(C)N | O=[N+:3]([O-])[CH:2]([CH3:1])[CH2:4][c:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][c:21]12>>[CH3:1][CH:2]([NH2:3])[CH2:4][c:5]1[cH:6][nH:7][c:8]2[cH:9][cH:10][c:11]([O:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][c:21]12 | CC(Cc1c[nH]c2ccc(OCc3ccccc3)cc12)[N+](=O)[O-] | CC(N)Cc1c[nH]c2ccc(OCc3ccccc3)cc12 | null | null | C(C)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(COc2ccc3[nH]ccc3c2)cc1 | O=[N+;H0;D3:1](-[O-])-[C:2](-[C:3])-[C;D1;H3:4]>>[C:3]-[C:2](-[C;D1;H3:4])-[NH2;D1;+0:1] | 51.1 | [{"value": 51.1, "product": "C(C1=CC=CC=C1)OC=1C=C2C(=CNC2=CC1)CC(C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a stirred suspension of lithium aluminum hydride (700 mg) in diethyl ether (25 mL) was slowly added a solution of 5-benzyloxy-3-(2-nitro-propyl)-1H-indole (650 mg) in diethyl ether (10 mL). The mixture was refluxed for 2 h. After cooling to rt, the reaction was quenched sequentially with 0.7 mL water, 0.7 mL 3 M aqu... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2[nH]ccc2c1.c1ccccc1 | Other | C(C)OCC | null | 0.5 | CC(Cc1c[nH]c2ccc(OCc3ccccc3)cc12)[N+](=O)[O-]>C(C)OCC>CC(N)Cc1c[nH]c2ccc(OCc3ccccc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d05eca1dd2af4e6f9d22796c7e4a4373 | C=O.CC(N)Cc1c[nH]c2ccc(OCc3ccccc3)cc12>>CC1Cc2c([nH]c3ccc(OCc4ccccc4)cc23)CN1 | C(C1=CC=CC=C1)OC=1C=C2C(=CNC2=CC1)CC(C)N.C=O.C(C)(=O)O>>C(C1=CC=CC=C1)OC=1C=C2C=3CC(NCC3NC2=CC1)C | O=[CH2:21].[CH3:1][CH:2]([CH2:3][c:4]1[cH:5][nH:6][c:7]2[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][c:20]12)[NH2:22]>>[CH3:1][CH:2]1[CH2:3][c:4]2[c:5]([nH:6][c:7]3[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]4[cH:14][cH:15][cH:16][cH:17][cH:18]4)[cH:19][c:20]23)[CH2:21][NH:22]1 | C=O.CC(N)Cc1c[nH]c2ccc(OCc3ccccc3)cc12 | CC1Cc2c([nH]c3ccc(OCc4ccccc4)cc23)CN1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 9266c73c6bd92c1e1d5661d1c7ea0b602764aa1f6f11776c4b52067dc1538fcc | cf32f1267c674fd84d46b8a676a46bd4e3a018dea282d34ea9ab93d79b66d0ee | c1ccc(COc2ccc3[nH]c4c(c3c2)CCNC4)cc1 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[C:3](-[NH2;D1;+0:4])-[C:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[cH;D2;+0:10]:1>>[C;D1;H3:2]-[C:3]1-[C:5]-[c:6]2:[c:7]:[c:8]:[#7;a:9]:[c;H0;D3;+0:10]:2-[CH2;D2;+0:1]-[NH;D2;+0:4]-1 | 65.1 | [{"value": 65.1, "product": "C(C1=CC=CC=C1)OC=1C=C2C=3CC(NCC3NC2=CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A mixture of 2-(5-benzyloxy-1H-indol-3-yl)-1-methyl-ethylamine (58 mg, 0.21 mmol), 37% formaldehyde (17 uL, 0.23 mmol) and ethanol (2 ml) was heated in a sealed tube at 80° C. for 2 h. The mixture was cooled to rt and acetic acid (60.6 uL, 1.05 mmol) was added. The mixture was heated again in a sealed tube at 80° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Secondary amine | c1ccc2[nH]ccc2c1 | c1ccc2c3c([nH]c2c1)CNCC3 | c1ccc2c3c([nH]c2c1)CNCC3.c1ccccc1 | HO- | C(C)O | 80 | null | C=O.CC(N)Cc1c[nH]c2ccc(OCc3ccccc3)cc12>C(C)O>CC1Cc2c([nH]c3ccc(OCc4ccccc4)cc23)CN1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6e073a3a3c75488e81aeb22ebd875f71 | CC1Cc2c([nH]c3ccc(OCc4ccccc4)cc23)CN1>>CC1Cc2c([nH]c3ccc(O)cc23)CN1 | C(C1=CC=CC=C1)OC=1C=C2C=3CC(NCC3NC2=CC1)C>>CC1NCC=2NC3=CC=C(C=C3C2C1)O | c1ccc(C[O:11][c:10]2[cH:9][cH:8][c:7]3[nH:6][c:5]4[c:4]([c:13]3[cH:12]2)[CH2:3][CH:2]([CH3:1])[NH:15][CH2:14]4)cc1>>[CH3:1][CH:2]1[CH2:3][c:4]2[c:5]([nH:6][c:7]3[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]23)[CH2:14][NH:15]1 | CC1Cc2c([nH]c3ccc(OCc4ccccc4)cc23)CN1 | CC1Cc2c([nH]c3ccc(O)cc23)CN1 | null | [Pd] | C(C)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c3c([nH]c2c1)CNCC3 | [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] | 72.3 | [{"value": 72.3, "product": "CC1NCC=2NC3=CC=C(C=C3C2C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A solution of 6-benzyloxy-3-methyl-2,3,4,9-tetrahydro-1H-β-carboline (60 mg) in ethanol (4 mL) was added to a suspension of 10% Pd/C (100 mg) in ethanol (10 mL). The mixture was stirred at rt for 16 h under an atmosphere of hydrogen. The mixture was filtered through celite and evaporation of the filtrate yielded 3-meth... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccc2c3c([nH]c2c1)CNCC3 | Other | [Pd].C(C)O | null | 16 | CC1Cc2c([nH]c3ccc(OCc4ccccc4)cc23)CN1>[Pd].C(C)O>CC1Cc2c([nH]c3ccc(O)cc23)CN1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-71c59c4825cc4dd98d2a6241a5eac55b | CC(=O)OC(C)=O.CCNc1ccc(OC)cc1>>COc1ccc(CCNC(C)=O)cc1 | COC1=CC=C(C=C1)NCC.C(C)N(CC)CC.C(C)(=O)OC(C)=O>>COC1=CC=C(C=C1)CCNC(C)=O | CC(=O)O[C:10]([CH3:11])=[O:12].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:9][CH2:8][CH3:7])[cH:13][cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][NH:9][C:10]([CH3:11])=[O:12])[cH:13][cH:14]1 | CC(=O)OC(C)=O.CCNc1ccc(OC)cc1 | COc1ccc(CCNC(C)=O)cc1 | null | null | ClCCl | Acylation | OtherReaction | f84cb424eca19d0f01a2c9486fe4404bd571d5320174f92f5d9317a9c8f7d146 | e10cc2d0356f91a769578cdf06c297fa361e6932d3e5ec3df3b0e48688c7ad1c | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[CH3;D1;+0:4]-[C:5]-[NH;D2;+0:6]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:6]-[C:5]-[CH2;D2;+0:4]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11] | null | [] | null | null | 3 | HOUR | To a mixture of (4-methoxy-phenyl)-ethylamine (10 g, Aldrich, U.S.A.) and triethylamine (10.1 mL) in dichloromethane (200 mL) was added acetic anhydride (7.4 g). The mixture was stirred at rt for 3 h and was washed successively with hydrochloric acid (1 M, 100 mL), 10% aqueous potassium carbonate (100 mL) and brine (10... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amine | Secondary amide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | ClCCl | null | 3 | CC(=O)OC(C)=O.CCNc1ccc(OC)cc1>ClCCl>COc1ccc(CCNC(C)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-30b35afd736244dbb5dcce6e7edbcd5b | COc1ccc(CCNC(C)=O)cc1>>COc1ccc2c(c1)C(C)=NCC2 | P(=O)(Cl)(Cl)Cl.COC1=CC=C(C=C1)CCNC(C)=O>>COC1=CC=C2CCN=C(C2=C1)C | O=[C:9]([CH3:10])[NH:11][CH2:12][CH2:13][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][cH:7]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH3:10])=[N:11][CH2:12][CH2:13]2 | COc1ccc(CCNC(C)=O)cc1 | COc1ccc2c(c1)C(C)=NCC2 | null | null | C(C)#N | Functional Group Interconversion | OtherReaction | 3d130227d6289b603b0e08a0df168cbdf5b579486c532fbe046c60faa6f7b086 | 9a0028c9231ad50183d9c88210ee9a64bc3340b25c296d3055a236dfcf8224cb | C1=NCCc2ccccc21 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:3]-[C:4]-[C:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[C;D1;H3:2]-[C;H0;D3;+0:1]1=[N;H0;D2;+0:3]-[C:4]-[C:5]-[c:6](:[c:7]):[c;H0;D3;+0:8]-1:[c:9]:[c:10] | 45.3 | [{"value": 45.3, "product": "COC1=CC=C2CCN=C(C2=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | Phosphorus oxychloride (22.5 mL) was added to a solution of N-[2-(4-methoxy-phenyl)-ethyl]-acetamide (6.5 g) in acetonitrile (200 mL). The mixture was heated at 120° C. in a sealed tube for 16 h. The solvent was evaporated. The residue was dissolved in dichloromethane (200 mL) and washed with aqueous sodium bicarbonate... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Substituted imine | c1ccccc1 | C1=NCCc2ccccc21 | C1=NCCc2ccccc21 | HO- | C(C)#N | 120 | null | COc1ccc(CCNC(C)=O)cc1>C(C)#N>COc1ccc2c(c1)C(C)=NCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ac6e3f79f8e84358b70ca30390b52cd6 | COc1ccc2c(c1)C(C)=NCC2>>COc1ccc2c(c1)C(C)NCC2 | C(#N)[BH3-].[Na+].COC1=CC=C2CCN=C(C2=C1)C.C([O-])(O)=O.[Na+]>>COC1=CC=C2CCNC(C2=C1)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9]([CH3:10])=[N:11][CH2:12][CH2:13]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH:9]([CH3:10])[NH:11][CH2:12][CH2:13]2 | COc1ccc2c(c1)C(C)=NCC2 | COc1ccc2c(c1)C(C)NCC2 | null | null | CO | Reduction | OtherReaction | d910bcf4f5bc5afea42a76e217bff0f95943b3d2f7ebee616a018ad6144c3bae | 469efbca661320a0d72c32f19625ec46edbc3ad7686cf46fdd0591eb136a8d7e | c1ccc2c(c1)CCNC2 | [C;D1;H3:1]-[C;H0;D3;+0:2]1=[N;H0;D2;+0:3]-[C:4]-[C:5]-[c:6]:[c:7]-1:[c:8]>>[C;D1;H3:1]-[CH;D3;+0:2]1-[NH;D2;+0:3]-[C:4]-[C:5]-[c:6]:[c:7]-1:[c:8] | 94.4 | [{"value": 94.4, "product": "COC1=CC=C2CCNC(C2=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Sodium cyanoborohydride (0.43 g) was added to a solution of 7-methoxy-1-methyl-3,4-dihydro-isoquinoline (2.67 g) in methanol (41 mL). The mixture was stirred at rt for 20 min. Aqueous sodium bicarbonate (saturated, 10 mL) was added to quench the excess hydride reagent. The methanol was evaporated under vacuum and the a... | 10.6084/m9.figshare.5104873.v1 | null | Substituted imine | Secondary amine | C1=NCCc2ccccc21 | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2 | null | CO | null | 0.333333 | COc1ccc2c(c1)C(C)=NCC2>CO>COc1ccc2c(c1)C(C)NCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1d4751cb30e84af5b29c7786c143530d | COc1ccc2c(c1)C(C)NCC2>>CC1NCCc2ccc(O)cc21 | Br.COC1=CC=C2CCNC(C2=C1)C>>Br.CC1NCCC2=CC=C(C=C12)O | C[O:11][c:10]1[cH:9][cH:8][c:7]2[c:13]([cH:12]1)[CH:3]([CH3:2])[NH:4][CH2:5][CH2:6]2>>[CH3:2][CH:3]1[NH:4][CH2:5][CH2:6][c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]21 | COc1ccc2c(c1)C(C)NCC2 | CC1NCCc2ccc(O)cc21 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2c(c1)CCNC2 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | Hydrobromic acid (48%, 46 mL) was added to the 7-methoxy-1-methyl-1,2,3,4-tetrahydro-isoquinoline (2.55 g) and the resulting mixture was heated at reflux for 16 h. Evaporation of the hydrobromic acid, followed by trituation with ethyl acetate (3×) afforded 1-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ol hydrogen bromide (... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2c(c1)CCNC2 | Other | null | null | null | COc1ccc2c(c1)C(C)NCC2>>CC1NCCc2ccc(O)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e7cbb3815910472891528b46b72c15cf | CC(=O)OC(C)=O.CCC(=O)Cl.CCNc1ccc(OC)cc1.COc1ccc(CCN)cc1C.COc1ccc(CCN)cc1OC>>CC1NCCc2cc(O)c(O)cc21.CCC1NCCc2ccc(O)cc21.Cc1cc2c(cc1O)C(C)NCC2 | C(CC)(=O)Cl.COC=1C=C(C=CC1OC)CCN.CC=1C=C(C=CC1OC)CCN.COC1=CC=C(C=C1)NCC.C(C)(=O)OC(C)=O>>C(C)C1NCCC2=CC=C(C=C12)O.CC1NCCC2=CC(=C(C=C12)O)O.CC1NCCC2=CC(=C(C=C12)O)C | CC(=O)O[C:35](=O)[CH3:5].O=[C:16](Cl)[CH2:15][CH3:14].[CH3:1][CH2:2][NH:3][c:6]1[cH:13][cH:12][c:10]([O:11][CH3:4])[cH:25][cH:26]1.[CH3:27][c:28]1[cH:29][c:30]([CH2:39][CH2:38][NH2:37])[cH:31][cH:32][c:33]1[O:34][CH3:36].C[O:9][c:8]1[cH:7][c:20]([CH2:19][CH2:18][NH2:17])[cH:21][cH:22][c:23]1[O:24]C>>[CH3:1][CH:2]1[NH:3... | CC(=O)OC(C)=O.CCC(=O)Cl.CCNc1ccc(OC)cc1.COc1ccc(CCN)cc1C.COc1ccc(CCN)cc1OC | CC1NCCc2cc(O)c(O)cc21.CCC1NCCc2ccc(O)cc21.Cc1cc2c(cc1O)C(C)NCC2 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 29d14da358f26f76de038bfcfdbefbecffc46177bbe74b649a40dcd521e7ce1e | e5b9c6ceab7b20564d639495e83b49368bd21745e8124e93806362a36c1b72ed | c1ccc2c(c1)CCNC2.c1ccc2c(c1)CCNC2.c1ccc2c(c1)CCNC2 | C-C(=O)-O-[C;H0;D3;+0:1](=O)-[CH3;D1;+0:2].C-[O;H0;D2;+0:3]-[c;H0;D3;+0:4]1:[c:5]:[c:6]:[c;H0;D3;+0:7](-[C:8]-[C:9]-[NH2;D1;+0:10]):[cH;D2;+0:11]:[c;H0;D3;+0:12]:1-[O;H0;D2;+0:13]-C.Cl-[C;H0;D3;+0:14](=O)-[C:15]-[C;D1;H3:16].[C;D1;H3:17]-[CH2;D2;+0:18]-[NH;D2;+0:19]-[c;H0;D3;+0:20]1:[cH;D2;+0:21]:[c:22]:[c;H0;D3;+0:23]... | null | [] | null | null | null | null | Similarly, 1-ethyl-1,2,3,4-tetrahydro-isoquinolin-7-ol was prepared by the above procedures by replacing the acetic anhydride in Procedure EEE with propionyl chloride. 1-Methyl-1,2,3,4-tetrahydro-isoquinoline-6,7-diol and 1,6-dimethyl-1,2,3,4-tetrahydro-isoquinolin-7-ol were prepared by replacing the (4-methoxy-phenyl)... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Anhydride.Ether.Ether.Ether.Ether.Primary amine.Primary amine.Secondary amine | Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Aromatic alcohol.Secondary amine.Secondary amine.Secondary amine | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccc2c(c1)CCNC2.c1ccc2c(c1)CCNC2.c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2.c1ccc2c(c1)CCNC2.c1ccc2c(c1)CCNC2 | HCl | null | null | null | CC(=O)OC(C)=O.CCC(=O)Cl.CCNc1ccc(OC)cc1.COc1ccc(CCN)cc1C.COc1ccc(CCN)cc1OC>>CC1NCCc2cc(O)c(O)cc21.CCC1NCCc2ccc(O)cc21.Cc1cc2c(cc1O)C(C)NCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f405ed59b2104cc7a767f0e2836109f2 | CC1Cc2ccc(O)cc2CN1.COc1ccc(CC(C)N)cc1>>COc1ccc(CC(C)=O)cc1.COc1ccc2c(c1)CNCC2.Oc1ccc2c(c1)CNCC2 | COC1=CC=C(C=C1)CC(C)N.CC1NCC2=CC(=CC=C2C1)O>>COC1=CC=C2CCNCC2=C1.C1NCCC2=CC=C(C=C12)O.COC1=CC=C(C=C1)CC(C)=O | [CH3:8][CH:23]1[NH:22][CH2:21][c:19]2[c:18]([cH:17][cH:16][c:15]([OH:10])[cH:20]2)[CH2:24]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][CH:34]([NH2:33])[CH3:35])[cH:11][cH:12]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C:8]([CH3:9])=[O:10])[cH:11][cH:12]1.[CH3:13][O:14][c:15]1[cH:16][cH:17][c:18]2[c:19]([cH:20]1)[CH... | CC1Cc2ccc(O)cc2CN1.COc1ccc(CC(C)N)cc1 | COc1ccc(CC(C)=O)cc1.COc1ccc2c(c1)CNCC2.Oc1ccc2c(c1)CNCC2 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | e0d1fb0c64421603d1f0572667ab29a6bd9256bed551bbf537a2838f3ac9c2f5 | 9ff0416bbd83dab48180f7136c92d7e2ee09ca2e0644c511ea308316868d05fb | c1ccc2c(c1)CCNC2.c1ccc2c(c1)CCNC2.c1ccccc1 | [CH3;D1;+0:1]-[CH;D3;+0:2](-[NH2;D1;+0:3])-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7].[CH3;D1;+0:8]-[CH;D3;+0:9]1-[#7:10]-[C:11]-[c:12]2:[c:13]:[c;H0;D3;+0:14](-[OH;D1;+0:15]):[c:16]:[c:17]:[c:18]:2-[C:19]-1>>[C;D1;H3:20]-[#8:21]-[c;H0;D3;+0:14]1:[c:16]:[c:17]:[c:18]2:[c:12](:[c:13]:1)-[C:11]-[#7:10]-[CH2;D2;+0:9]-[C:19]-2.[C;D... | null | [] | null | null | null | null | 7-Methoxy-1,2,3,4-tetrahydro-isoquinoline and 1,2,3,4-tetrahydro-isoquinolin-7-ol were prepared by a literature procedure (J. Med. Chem. 1987, 30, 2208–2216). 2-(4-Methoxy-phenyl)-1-methyl-ethylamine required for the preparation of 3-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ol was obtained from 1-(4-methoxy-phenyl)-prop... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine | Ketone.Ether.Aromatic alcohol.Secondary amine | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2.c1ccc2c(c1)CCNC2 | c1ccccc1.c1ccc2c(c1)CCNC2.c1ccc2c(c1)CCNC2 | Other | null | null | null | CC1Cc2ccc(O)cc2CN1.COc1ccc(CC(C)N)cc1>>COc1ccc(CC(C)=O)cc1.COc1ccc2c(c1)CNCC2.Oc1ccc2c(c1)CNCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-74c281cf5f35456f95f2ed72d145c0cd | CC(=O)N1CCc2ccc(S(=O)(=O)Cl)cc2C1.[NH4+]>>Cl.NS(=O)(=O)c1ccc2c(c1)CNCC2 | C(C)(=O)N1CC2=CC(=CC=C2CC1)S(=O)(=O)Cl.[OH-].[NH4+]>>Cl.NS(=O)(=O)C1=CC=C2CCNCC2=C1 | CC(=O)[N:13]1[CH2:12][c:10]2[c:9]([cH:8][cH:7][c:6]([S:3]([Cl:1])(=[O:4])=[O:5])[cH:11]2)[CH2:15][CH2:14]1.[NH4+:2]>>[ClH:1].[NH2:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][NH:13][CH2:14][CH2:15]2 | CC(=O)N1CCc2ccc(S(=O)(=O)Cl)cc2C1.[NH4+] | Cl.NS(=O)(=O)c1ccc2c(c1)CNCC2 | null | null | null | Acylation | OtherReaction | 4822a6f8ba470df547671b5d980346ae85823deb027fe736e9611a9482c10d9d | 3b8068aab1cf0448cbb855780ec50f8b2896e7f98548e69bb9c61a7e43ec7b1d | c1ccc2c(c1)CCNC2 | C-C(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3]:[c:4]:[c:5](-[S;H0;D4;+0:6](-[Cl;H0;D1;+0:7])(=[O;D1;H0:8])=[O;D1;H0:9]):[c:10])-[C:11]-[C:12].[NH4+;D0:13]>>[C:12]-[C:11]-[NH;D2;+0:1]-[C:2]-[c:3]:[c:4]:[c:5](-[S;H0;D4;+0:6](-[NH2;D1;+0:13])(=[O;D1;H0:8])=[O;D1;H0:9]):[c:10].[ClH;D0;+0:7] | null | [] | null | null | 16 | HOUR | Ammonium hydroxide (conc., 20 mL) was added to 2-acetyl-1,2,3,4-tetrahydro-isoquinoline-7-sulfonyl chloride (2 g). The mixture was stirred at rt for 16 h. The ammonium hydroxide was evaporated under vacuum and hydrochloric acid (10%, 50 mL) was added to the residue. The mixture was heated at reflux for 4 h and the aque... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Sulfonyl halide | Sulfonamide.Secondary amine | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2 | HO- | null | null | 16 | CC(=O)N1CCc2ccc(S(=O)(=O)Cl)cc2C1.[NH4+]>>Cl.NS(=O)(=O)c1ccc2c(c1)CNCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4fa4e9c4bf0048689c33242d888f1867 | CC(=O)N1CCc2ccc(S(=O)(=O)Cl)cc2C1.CN>>CNS(=O)(=O)c1ccc2c(c1)CNCC2.Cl | CN.C(C)(=O)N1CC2=CC(=CC=C2CC1)S(=O)(=O)Cl>>Cl.CNS(=O)(=O)C1=CC=C2CCNCC2=C1 | CC(=O)[N:13]1[CH2:12][c:10]2[c:9]([cH:8][cH:7][c:6]([S:3](=[O:4])(=[O:5])[Cl:16])[cH:11]2)[CH2:15][CH2:14]1.[CH3:1][NH2:2]>>[CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]2[c:10]([cH:11]1)[CH2:12][NH:13][CH2:14][CH2:15]2.[ClH:16] | CC(=O)N1CCc2ccc(S(=O)(=O)Cl)cc2C1.CN | CNS(=O)(=O)c1ccc2c(c1)CNCC2.Cl | null | null | CO | Acylation | OtherReaction | fe60f003cd190fa50f5510acc547c61f90192acdb7bc0ce58caa021974851ac1 | 8428a752f1c8577e4e9c8ffeec828b03c7ee03aea400d2031cba94bc22c40c71 | c1ccc2c(c1)CCNC2 | C-C(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3]:[c:4]:[c:5](-[S;H0;D4;+0:6](-[Cl;H0;D1;+0:7])(=[O;D1;H0:8])=[O;D1;H0:9]):[c:10])-[C:11]-[C:12].[C;D1;H3:13]-[NH2;D1;+0:14]>>[C:12]-[C:11]-[NH;D2;+0:1]-[C:2]-[c:3]:[c:4]:[c:5](-[S;H0;D4;+0:6](=[O;D1;H0:8])(=[O;D1;H0:9])-[NH;D2;+0:14]-[C;D1;H3:13]):[c:10].[ClH;D0;+0:7] | null | [] | null | null | 16 | HOUR | Methylamine in methanol (2 M, 20 mL) was added to 2-acetyl-1,2,3,4-tetrahydro-isoquinoline-7-sulfonyl chloride (2 g). The mixture was stirred at rt for 16 h. Excess methylamine and methanol were evaporated under vacuum and hydrochloric acid (10%, 30 mL) was added to the residue. The mixture was heated at reflux for 3 h... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary amine.Sulfonyl halide | Sulfonamide.Secondary amine | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2 | HO- | CO | null | 16 | CC(=O)N1CCc2ccc(S(=O)(=O)Cl)cc2C1.CN>CO>CNS(=O)(=O)c1ccc2c(c1)CNCC2.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-714bcac5916344f08948f90775ba368f | COC(=O)c1ccc(OC)cc1C(=O)OC>>COc1ccc2c(c1)C(=O)OC2=O | Cl.COC(C=1C(C(=O)OC)=CC(=CC1)OC)=O.[OH-].[Na+]>>COC=1C=C2C(OC(C2=CC1)=O)=O | CO[C:9]([c:7]1[c:6]([C:12]([O:11]C)=[O:13])[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]1)=[O:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[O:11][C:12]2=[O:13] | COC(=O)c1ccc(OC)cc1C(=O)OC | COc1ccc2c(c1)C(=O)OC2=O | null | null | CO | Miscellaneous | OtherReaction | 6b6e371c9fe3ba7f1617a5ca6a2995d84bec575603645e5ac4552a1810bd4605 | 49a8abb00986d31e7ee8f04e3890cf8743fa6008a06052d95cb247a6ee1ee99e | O=C1OC(=O)c2ccccc21 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[O;H0;D2;+0:8]-[C:6](=[O;D1;H0:7])-[c:5]:[c:3]-1:[c:4] | 50.8 | [{"value": 50.8, "product": "COC=1C=C2C(OC(C2=CC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-methoxyphthalic acid dimethyl ester (3.1 g, Fluka, U.S.A.) in 10 mL methanol and 35 mL of a 1 M solution of aqueous sodium hydroxide was heated to reflux for 3 hours. The solution was allowed to cool to rt, acidified to pH 2 with 1 M hydrochloric acid, and extracted three times with ethyl acetate. The o... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Anhydride | null | c1ccc2c(c1)COC2 | c1ccc2c(c1)COC2 | HO- | CO | null | null | COC(=O)c1ccc(OC)cc1C(=O)OC>CO>COc1ccc2c(c1)C(=O)OC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9072369a27fd440b9e7ba1134c44b63f | COc1ccc2c(c1)CCN=C2C.O=C(Cl)OCc1ccccc1>>C=C1c2ccc(OC)cc2CCN1C(=O)OCc1ccccc1 | ClC(=O)OCC1=CC=CC=C1.COC=1C=C2CCN=C(C2=CC1)C.C(C)N(CC)CC>>C(C1=CC=CC=C1)OC(=O)N1C(C2=CC=C(C=C2CC1)OC)=C | [CH3:1][C:2]1=[N:13][CH2:12][CH2:11][c:10]2[c:3]1[cH:4][cH:5][c:6]([O:7][CH3:8])[cH:9]2.Cl[C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH2:1]=[C:2]1[c:3]2[cH:4][cH:5][c:6]([O:7][CH3:8])[cH:9][c:10]2[CH2:11][CH2:12][N:13]1[C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:2... | COc1ccc2c(c1)CCN=C2C.O=C(Cl)OCc1ccccc1 | C=C1c2ccc(OC)cc2CCN1C(=O)OCc1ccccc1 | null | null | ClCCl | Protection | OtherReaction | 45bc397217b12e71448812737af9528edb34da5185bb63fd5fb8648f5b1d0679 | 33cd800e4874e806fbe718e7fcd9caed85ebffc65bd7c8572b2ebc27dbf9a22a | C=C1c2ccccc2CCN1C(=O)OCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[CH3;D1;+0:5]-[C;H0;D3;+0:6]1=[N;H0;D2;+0:7]-[C:8]-[C:9]-[c:10]:[c:11]-1:[c:12]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7]1-[C:8]-[C:9]-[c:10]:[c:11](:[c:12])-[C;H0;D3;+0:6]-1=[CH2;D1;+0:5] | null | [] | null | null | 0.5 | HOUR | Benzyl chloroformate (0.30 mL) was added to an ice-cold solution of 6-methoxy-1-methyl-3,4-dihydroisoquinoline (0.36 g) and triethylamine (0.58 mL) in 10 mL dichloromethane. After 0.5 h, the volatile material was evaporated to furnish 0.66 g of 6-methoxy-1-methylene-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Substituted imine | Enamine.Carbamic ester | C1=NCCc2ccccc21 | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CC[NH]C2.c1ccccc1 | HCl | ClCCl | null | 0.5 | COc1ccc2c(c1)CCN=C2C.O=C(Cl)OCc1ccccc1>ClCCl>C=C1c2ccc(OC)cc2CCN1C(=O)OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-20d207dccb154960a6a6d8d38ffea590 | C=C1c2ccc(OC)cc2CCN1C(=O)OCc1ccccc1>>COc1ccc2c(c1)CCN(C(=O)OCc1ccccc1)C(=O)C2 | C(C1=CC=CC=C1)OC(=O)N1C(C2=CC=C(C=C2CC1)OC)=C.C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].C(C)(=O)[O-].[Pb+4]>>C(C1=CC=CC=C1)OC(=O)N1C(CC2=C(CC1)C=C(C=C2)OC)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[C:22]2=[CH2:24]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[C:22](=[O:2... | C=C1c2ccc(OC)cc2CCN1C(=O)OCc1ccccc1 | COc1ccc2c(c1)CCN(C(=O)OCc1ccccc1)C(=O)C2 | null | null | C(C)(=O)O | Oxidation | OtherReaction | 70dfda8d1b8b2a6284fda81905462b9551930136d814244a658bab832340303d | 7ef94548098a07efb37991201ddddd8c6b5dc1b4ed68e4abb2ce17c9099ca0e3 | O=C1Cc2ccccc2CCN1C(=O)OCc1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](:[c:10]:[c:11])-[C;H0;D3;+0:12]-1=[CH2;D1;+0:13]>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](:[c:10]:[c:11])-[CH2;D2;+0:13]-[C;H0;D3;+0:12]-1=[O;D1;H0:14] | 28.8 | [{"value": 28.8, "product": "C(C1=CC=CC=C1)OC(=O)N1C(CC2=C(CC1)C=C(C=C2)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 6-methoxy-1-methylene-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (0.66 g) in 20 mL of glacial acetic acid was added lead tetraacetate (1 g). The reaction was stirred overnight, then quenched by the addition of 2 mL of glycerol. The volatile material was evaporated and the resulting resi... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Substituted dicarboximide | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CC[NH]CC2 | c1ccc2c(c1)CC[NH]CC2.c1ccccc1 | Other | C(C)(=O)O | null | 8 | C=C1c2ccc(OC)cc2CCN1C(=O)OCc1ccccc1>C(C)(=O)O>COc1ccc2c(c1)CCN(C(=O)OCc1ccccc1)C(=O)C2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-141213c897394fb3aee98326e828dc45 | COc1ccc2c(c1)CCCC2=O>>COc1ccc2c(c1)CCCNC2=O | C([O-])([O-])=O.[K+].[K+].[N-]=[N+]=[N-].[Na+].COC=1C=C2CCCC(C2=CC1)=O>>COC1=CC2=C(C(NCCC2)=O)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH2:11][C:13]2=[O:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH2:11][NH:12][C:13]2=[O:14] | COc1ccc2c(c1)CCCC2=O | COc1ccc2c(c1)CCCNC2=O | null | null | Cl | Functional Group Addition | Schmidt ketone amide | 49e900339591aa4192907adb8a85aeba4b1fb0218669f100a6551598042fdcc9 | 2eb609f54422c0279557c5451dffbcf43fa7dc53a915eee10665042f34f6a171 | O=C1NCCCc2ccccc21 | [O;D1;H0:1]=[C;H0;D3;+0:2]1-[CH2;D2;+0:3]-[C:4]-[C:5]-[c:6]:[c:7]-1:[c:8]>>[O;D1;H0:1]=[C;H0;D3;+0:2]1-[#7:9]-[CH2;D2;+0:3]-[C:4]-[C:5]-[c:6]:[c:7]-1:[c:8] | null | [] | null | null | 20 | HOUR | Sodium azide (0.37 g) was slowly added in portions to a stirring ice-cold suspension of 6-methoxy-3,4-dihydro-2H-naphthalen-1-one in 10 mL of concentrated hydrochloric acid. The mixture was allowed to slowly warm to room temperature and stirred for 20 h. The mixture was poured onto ice and carefully neutralized with so... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary amide | c1ccc2c(c1)CCCC2 | c1ccc2c(c1)CCCNC2 | c1ccc2c(c1)CCCNC2 | Other | Cl | null | 20 | COc1ccc2c(c1)CCCC2=O>Cl>COc1ccc2c(c1)CCCNC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-366c487f99fe4d4cb442dff8b04764dd | O=C(O)/C=C/c1cnc[nH]1>>O=C(O)CCc1cnc[nH]1 | CO.C1=C(NC=N1)/C=C/C(=O)O.C1=C(NC=N1)/C=C/C(=O)O>>N1C=NC=C1CCC(=O)O | [O:1]=[C:2]([OH:3])/[CH:4]=[CH:5]/[c:6]1[cH:7][n:8][cH:9][nH:10]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][c:6]1[cH:7][n:8][cH:9][nH:10]1 | O=C(O)/C=C/c1cnc[nH]1 | O=C(O)CCc1cnc[nH]1 | null | [Pd] | Cl | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1c[nH]cn1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])/[CH;D2;+0:4]=[CH;D2;+0:5]/[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:1>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:1 | null | [] | null | null | 8 | HOUR | Urocanic acid (compound i, where R2 is H)(1.38 g, 10.0 mmol) was dissolved in 5% aqueous HCl (20 ml) plus MeOH (15 ml) containing 10% Pd on carbon (100 mg) and the mixture was shaken overnight under about 30 psi H2. The catalyst was removed by filtration through a 3 cm pad of diatomaceous earth and the filtrate was con... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1c[nH]cn1 | null | [Pd].Cl | null | 8 | O=C(O)/C=C/c1cnc[nH]1>[Pd].Cl>O=C(O)CCc1cnc[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ef9670467ce042908837aa3201aad1a7 | CCCC[C@H](NC(=O)OCc1ccccc1)c1nc(-c2ccccc2OC)cn1CC(=O)OCC>>CCCCC1=NC(=O)Cn2cc(-c3ccccc3OC)nc21 | C(C)OC(CN1C(=NC(=C1)C1=C(C=CC=C1)OC)[C@H](CCCC)NC(=O)OCC1=CC=CC=C1)=O>>C(CCC)C=1C=2N(CC(N1)=O)C=C(N2)C2=C(C=CC=C2)OC | CCO[C:7](=[O:8])[CH2:9][n:10]1[cH:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[O:19][CH3:20])[n:21][c:22]1[C@H:5]([CH2:4][CH2:3][CH2:2][CH3:1])[NH:6]C(=O)OCc1ccccc1>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1=[N:6][C:7](=[O:8])[CH2:9][n:10]2[cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[O:19][CH3:20])[n:21]... | CCCC[C@H](NC(=O)OCc1ccccc1)c1nc(-c2ccccc2OC)cn1CC(=O)OCC | CCCCC1=NC(=O)Cn2cc(-c3ccccc3OC)nc21 | null | [Pd] | CC(=O)O | Functional Group Interconversion | OtherReaction | 0d9e506bdb27b2a914459a10573bcce2bb30e095b8ab204847fed2c0e2e6a1c7 | ae018a397d89ef8eb9360d83a5906655aac51d703af7115c1ddc4824f1d4ea86 | O=C1Cn2cc(-c3ccccc3)nc2C=N1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:1-[C@H;D3;+0:9](-[C:10]-[C:11])-[NH;D2;+0:12]-C(=O)-O-C-c1:c:c:c:c:c:1>>[C:11]-[C:10]-[C;H0;D3;+0:9]1=[N;H0;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7;a:4]2:[c:5]:[c:6]:[#7;a:7]:[c:8]:2-1 | 87 | [{"value": 87.0, "product": "C(CCC)C=1C=2N(CC(N1)=O)C=C(N2)C2=C(C=CC=C2)OC", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 3 | HOUR | The product from Step 1.d. (compound v where R3 is n-butyl, R4 is 2-methoxyphenyl, and R5 and R6 are H) (11.5 g, 23.9 mmol) was dissolved in HOAc (100 ml) containing 10% Pd on carbon catalyst (500 mg) and hydrogenated under 50 psi of H2 for about 3 hours at room temperature. The catalyst was removed by filtration throu... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether | Substituted imine | c1ccccc1 | C1=NCCn2ccnc21 | C1=NCCn2ccnc21.c1ccccc1 | HO- | [Pd].CC(=O)O | 70 | 3 | CCCC[C@H](NC(=O)OCc1ccccc1)c1nc(-c2ccccc2OC)cn1CC(=O)OCC>[Pd].CC(=O)O>CCCCC1=NC(=O)Cn2cc(-c3ccccc3OC)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-385bbc0308b1431c9eb6627be4f10839 | CCCCC1=NC(=O)Cn2cc(-c3ccccc3OC)nc21>>CCCCC1NCCn2cc(-c3ccccc3OC)nc21 | C(=O)([O-])[O-].[K+].[K+].C(CCC)C=1C=2N(CC(N1)=O)C=C(N2)C2=C(C=CC=C2)OC.Cl>>C(CCC)C1C=2N(CCN1)C=C(N2)C2=C(C=CC=C2)OC | O=[C:7]1[N:6]=[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:21]2[n:9]([cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[O:18][CH3:19])[n:20]2)[CH2:8]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[NH:6][CH2:7][CH2:8][n:9]2[cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[O:18][CH3:19])[n:20][c:21]21 | CCCCC1=NC(=O)Cn2cc(-c3ccccc3OC)nc21 | CCCCC1NCCn2cc(-c3ccccc3OC)nc21 | null | null | C1CCOC1 | Reduction | OtherReaction | 71e03d3fe6ecedf179589cd00771ad8e8fb06fca88401c3088551ab64f803d00 | 469efbca661320a0d72c32f19625ec46edbc3ad7686cf46fdd0591eb136a8d7e | c1ccc(-c2cn3c(n2)CNCC3)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[#7;a:3]2:[c:4]:[c:5]:[#7;a:6]:[c:7]:2-[C;H0;D3;+0:8](-[C:9]-[C:10])=[N;H0;D2;+0:11]-1>>[C:10]-[C:9]-[CH;D3;+0:8]1-[NH;D2;+0:11]-[CH2;D2;+0:1]-[C:2]-[#7;a:3]2:[c:4]:[c:5]:[#7;a:6]:[c:7]:2-1 | 92 | [{"value": 92.0, "product": "C(CCC)C1C=2N(CCN1)C=C(N2)C2=C(C=CC=C2)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The product from Step 1.e. (6.13 g, 20.5 mmol) (compound vi where R3 is n-butyl, R4 is 2-methoxyphenyl, and R5 and R6 are H) was dissolved in THF (100 ml) and treated with 1M BH3H/TF (82.0 ml, 82.0 mmol) at room temperature for about 2 hours and then refluxed for about 3 hours. The mixture was cooled to room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Substituted imine | Secondary amine | C1=NCCn2ccnc21 | c1cn2c(n1)CNCC2 | c1cn2c(n1)CNCC2.c1ccccc1 | Other | C1CCOC1 | null | 2 | CCCCC1=NC(=O)Cn2cc(-c3ccccc3OC)nc21>C1CCOC1>CCCCC1NCCn2cc(-c3ccccc3OC)nc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-07fbb94ca125403ebc39e731af322d93 | CCCCC1c2nc(-c3ccccc3OC)cn2CCN1C(=O)CCc1cnc(C(=O)OC(C)(C)C)[nH]1>>CCCCC1c2nc(-c3ccccc3OC)cn2CCN1C(=O)CCc1cnc[nH]1 | C(CCC)C1C=2N(CCN1C(CCC1=CN=C(N1)C(=O)OC(C)(C)C)=O)C=C(N2)C2=C(C=CC=C2)OC.Cl>>C(CCC)C1C=2N(CCN1C(CCC1=CN=CN1)=O)C=C(N2)C2=C(C=CC=C2)OC | CC(C)(C)OC(=O)[c:29]1[n:28][cH:27][c:26]([CH2:25][CH2:24][C:22]([N:21]2[CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:6]3[n:7][c:8](-[c:9]4[cH:10][cH:11][cH:12][cH:13][c:14]4[O:15][CH3:16])[cH:17][n:18]3[CH2:19][CH2:20]2)=[O:23])[nH:30]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]1[c:6]2[n:7][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][c... | CCCCC1c2nc(-c3ccccc3OC)cn2CCN1C(=O)CCc1cnc(C(=O)OC(C)(C)C)[nH]1 | CCCCC1c2nc(-c3ccccc3OC)cn2CCN1C(=O)CCc1cnc[nH]1 | null | null | CO | Reduction | Decarboxylation | fbcd7878f9e8827b35e797ef93a74642f45544c45fddfbe1aca577a631b42980 | 819f23c772480c303ab85988e0c5df4366b1418d125c036e6f579b95e75e3482 | O=C(CCc1cnc[nH]1)N1CCn2cc(-c3ccccc3)nc2C1 | C-C(-C)(-C)-O-C(=O)-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:1>>[#7;a:2]1:[c:3]:[c:4]:[#7;a:5]:[cH;D2;+0:1]:1 | 47 | [{"value": 47.0, "product": "C(CCC)C1C=2N(CCN1C(CCC1=CN=CN1)=O)C=C(N2)C2=C(C=CC=C2)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | The product from Step 1.g. (450 mg, 0.89 mmol) was dissolved in MeOH (5 ml) and 4N HCl was added and the reaction was stirred at room temperature for about ½ hour. Solvents were removed under reduced pressure to yield 420 mg of crude product. Part of the crude (100 mg) was purified by preparative HPLC on a RAININ™ C18 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | null | c1c[nH]cn1 | c1c[nH]cn1 | c1cn2c(n1)C[NH]CC2.c1ccccc1.c1c[nH]cn1 | HO- | CO | null | 0.5 | CCCCC1c2nc(-c3ccccc3OC)cn2CCN1C(=O)CCc1cnc(C(=O)OC(C)(C)C)[nH]1>CO>CCCCC1c2nc(-c3ccccc3OC)cn2CCN1C(=O)CCc1cnc[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b7c13e6ceb0545a3b81fd45a3a9d8ec7 | CO.O=C(O)Cc1c[nH]cn1>>COC(=O)Cc1c[nH]cn1 | N1C=NC(=C1)CC(=O)O.[Na].CO>>N1C=NC(=C1)CC(=O)OC | [CH3:1][OH:2].O[C:3](=[O:4])[CH2:5][c:6]1[cH:7][nH:8][cH:9][n:10]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][nH:8][cH:9][n:10]1 | CO.O=C(O)Cc1c[nH]cn1 | COC(=O)Cc1c[nH]cn1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1c[nH]cn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4](:[#7;a:5]):[c:6]:[#7;a:7].[C;D1;H3:8]-[OH;D1;+0:9]>>[#7;a:5]:[c:4](-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C;D1;H3:8]):[c:6]:[#7;a:7] | null | [] | null | null | 0.5 | HOUR | A solution of 4-Imidazoleacetic acid, sodium salt, hydrate (compound ix, where R2 is H) (3.0 g, 18.1 mmol) in MeOH (50 ml) was cooled to about 0° C. and anhydrous HCl gas was bubbled into the mixture for about 15 minutes while maintaining reaction temperature below about 5° C. The reaction was stirred for about ½ hour ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1c[nH]cn1 | HO- | null | null | 0.5 | CO.O=C(O)Cc1c[nH]cn1>>COC(=O)Cc1c[nH]cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f14b9450f13e42b58be4c562d609b698 | COC(=O)Cc1c[nH]cn1.ClC(c1ccccc1)(c1ccccc1)c1ccccc1>>COC(=O)Cc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | N1C=NC(=C1)CC(=O)OC.ClC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCN(CC)CC>>C1(=CC=CC=C1)C(N1C=NC(=C1)CC(=O)OC)(C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][nH:8][cH:28][n:29]1.Cl[C:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][n:8]([C:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)([c:16]2[cH:1... | COC(=O)Cc1c[nH]cn1.ClC(c1ccccc1)(c1ccccc1)c1ccccc1 | COC(=O)Cc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e11c706bbc4ed4c537e0a88a7bb26c47a17011e98b2e37f239a30e81d0496061 | 677f263b618a481bcdc02c85060e6c44b1f44f328207057cd4782b98754b7773 | c1ccc(C(c2ccccc2)(c2ccccc2)n2ccnc2)cc1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[#8:11]-[C:12](=[O;D1;H0:13])-[C:14]-[c:15]1:[#7;a:16]:[c:17]:[nH;D2;+0:18]:[c:19]:1>>[#8:11]-[C:12](=[O;D1;H0:13])-[C:14]-[c:15]1:[#7;a:16]:[c:17]:[n;H0;D3;+0:18](-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9])... | 104 | [{"value": 104.0, "product": "C1(=CC=CC=C1)C(N1C=NC(=C1)CC(=O)OC)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | A solution of the product from Step 4.a. (3.2 g, 17.5 mmol) in DMF (50 ml) was treated with chlorotriphenylmethane (4.88 g, 17.5 mmol) and Et3N (5.4 ml, 38.5 mmol) and the reaction was stirred at room temperature for about 6 hours. The DMF was evaporated under reduced pressure and the residue was distributed between Et... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | null | 6 | COC(=O)Cc1c[nH]cn1.ClC(c1ccccc1)(c1ccccc1)c1ccccc1>CN(C)C=O>COC(=O)Cc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6cbd47be74554fafb353de8fa6d07f48 | ClC(c1ccccc1)(c1ccccc1)c1ccccc1.OCc1c[nH]cn1>>OCc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | Cl.OCC=1N=CNC1.Cl.OCC=1N=CNC1.ClC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCN(CC)CC>>OCC=1N=CN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | Cl[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[OH:1][CH2:2][c:3]1[cH:4][nH:5][cH:25][n:26]1>>[OH:1][CH2:2][c:3]1[cH:4][n:5]([C:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]2[cH:2... | ClC(c1ccccc1)(c1ccccc1)c1ccccc1.OCc1c[nH]cn1 | OCc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e11c706bbc4ed4c537e0a88a7bb26c47a17011e98b2e37f239a30e81d0496061 | 677f263b618a481bcdc02c85060e6c44b1f44f328207057cd4782b98754b7773 | c1ccc(C(c2ccccc2)(c2ccccc2)n2ccnc2)cc1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[C:11]-[c:12]1:[#7;a:13]:[c:14]:[nH;D2;+0:15]:[c:16]:1>>[C:11]-[c:12]1:[#7;a:13]:[c:14]:[n;H0;D3;+0:15](-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10]):[c:16]:1 | 78.3 | [{"value": 78.0, "product": "OCC=1N=CN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.3, "product": "OCC=1N=CN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Hydroxymethylimidazole hydrochloride (compound xiii where R2 is H) (2.50 g, 18.6 mmol) and Et3N (2.59 ml, 18.6 mmol) were combined in DMF (30 ml) and stirred at room temperature. A solution of chlorotriphenylmethane (5.19 g, 18.6 mmol) in DMF (25 ml) was added dropwise at room temperature and the resulting mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | null | null | ClC(c1ccccc1)(c1ccccc1)c1ccccc1.OCc1c[nH]cn1>CN(C)C=O>OCc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2dd48e91d9f149d4ba76a652ed59e760 | OCc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1>>O=Cc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | OCC=1N=CN(C1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CCN(CC)CC.O>>C1(=CC=CC=C1)C(N1C=NC(=C1)C=O)(C1=CC=CC=C1)C1=CC=CC=C1 | [OH:1][CH2:2][c:3]1[cH:4][n:5]([C:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[cH:25][n:26]1>>[O:1]=[CH:2][c:3]1[cH:4][n:5]([C:6]([c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]2[cH:20][... | OCc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | O=Cc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 | null | null | CS(=O)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(C(c2ccccc2)(c2ccccc2)n2ccnc2)cc1 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5](-[CH2;D2;+0:6]-[OH;D1;+0:7]):[c:8]:1>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5](-[CH;D2;+0:6]=[O;H0;D1;+0:7]):[c:8]:1 | null | [] | 110 | CELSIUS | null | null | The product from Step 8.a. (2.04 g, 6.00 mmol) was suspended in DMSO (10.0 ml) and Et3N (3.34 ml, 24.0 mmol) and SO3-pyridine complex (2.39 g, 15.0 mmol) were added at room temperature. The mixture was warmed at about 110° C. for about 1 hour and then allowed to cool. The mixture was poured into 150 ml H2O and the prod... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1c[nH]cn1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CS(=O)C | 110 | null | OCc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1>CS(=O)C>O=Cc1cn(C(c2ccccc2)(c2ccccc2)c2ccccc2)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0e8fc914af534bad8676cf7b7037aa71 | COc1ccccc1-c1cn2c(n1)C(CCO)N(C(=O)OC(C)(C)C)CC2.SC(c1ccccc1)(c1ccccc1)c1ccccc1>>COc1ccccc1-c1cn2c(n1)C(CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)N(C(=O)OC(C)(C)C)CC2 | CC(C)(OC(=O)N1C(C=2N(CC1)C=C(N2)C2=C(C=CC=C2)OC)CCO)C.CCOC(=O)/N=N/C(=O)OCC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)C(S)(C1=CC=CC=C1)C1=CC=CC=C1>>CC(C)(OC(=O)N1C(C=2N(CC1)C=C(N2)C2=C(C=CC=C2)OC)CCSC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C | O[CH2:16][CH2:15][CH:14]1[c:12]2[n:11]([cH:10][c:9](-[c:8]3[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]3)[n:13]2)[CH2:46][CH2:45][N:37]1[C:38](=[O:39])[O:40][C:41]([CH3:42])([CH3:43])[CH3:44].[SH:17][C:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)([c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[c:31]1[cH:32][cH:33][cH:3... | COc1ccccc1-c1cn2c(n1)C(CCO)N(C(=O)OC(C)(C)C)CC2.SC(c1ccccc1)(c1ccccc1)c1ccccc1 | COc1ccccc1-c1cn2c(n1)C(CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)N(C(=O)OC(C)(C)C)CC2 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 94a14d3014f7fdb5c4fa6f9f37d523bd85860ea21497647c55ba9393bbc36835 | f8355ba7e68f7d5b10019904f32df628ca7b7bc14adae6579e7d0de9afb40579 | c1ccc(-c2cn3c(n2)C(CCSC(c2ccccc2)(c2ccccc2)c2ccccc2)NCC3)cc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3]-[#7:4].[SH;D1;+0:5]-[C:6](-[c:7])(-[c:8])-[c:9]>>[#7:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:5]-[C:6](-[c:7])(-[c:8])-[c:9] | 111 | [{"value": 111.0, "product": "CC(C)(OC(=O)N1C(C=2N(CC1)C=C(N2)C2=C(C=CC=C2)OC)CCSC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 0.5 | HOUR | Triphenylphosphine (4.08 g, 15.5 mmol) was dissolved in THF (25 ml), cooled to about 0° C. under N2 and Diethylazodicarboxylate (2.45 ml, 15.54 mmol) was added at a dropwise rate so that the reaction temperature was maintained at about <3° C. Stirring was continued for about ½ hour at 0° C. A mixture of the triphenylme... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aliphatic thiol | Monosulfide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1cn2c(n1)C[NH]CC2 | HO- | C1CCOC1 | 0 | 0.5 | COc1ccccc1-c1cn2c(n1)C(CCO)N(C(=O)OC(C)(C)C)CC2.SC(c1ccccc1)(c1ccccc1)c1ccccc1>C1CCOC1>COc1ccccc1-c1cn2c(n1)C(CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)N(C(=O)OC(C)(C)C)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bc0ba97610434c6a8c9e80143daf1a08 | COc1ccccc1-c1cn2c(n1)C(CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)N(C(=O)OC(C)(C)C)CC2>>COc1ccccc1-c1cn2c(n1)C(CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)NCC2 | CC(C)(OC(=O)N1C(C=2N(CC1)C=C(N2)C2=C(C=CC=C2)OC)CCSC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C.C(=O)(O)[O-].[Na+]>>COC1=C(C=CC=C1)C=1N=C2N(CCNC2CCSC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C1 | CC(C)(C)OC(=O)[N:37]1[CH:14]([CH2:15][CH2:16][S:17][C:18]([c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)([c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[c:31]2[cH:32][cH:33][cH:34][cH:35][cH:36]2)[c:12]2[n:11]([cH:10][c:9](-[c:8]3[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]3)[n:13]2)[CH2:39][CH2:38]1>>[CH3:1][O:2][c:3]1[cH:4... | COc1ccccc1-c1cn2c(n1)C(CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)N(C(=O)OC(C)(C)C)CC2 | COc1ccccc1-c1cn2c(n1)C(CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)NCC2 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | 50881a0f5206784be890ae29efad1eb7c48349e710243625c7e9c8ae91f549ec | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2cn3c(n2)C(CCSC(c2ccccc2)(c2ccccc2)c2ccccc2)NCC3)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7;a:4]:[c:5](:[#7;a:6])-[C:7]-1-[C:8]>>[#7;a:6]:[c:5]1:[#7;a:4]-[C:3]-[C:2]-[NH;D2;+0:1]-[C:7]-1-[C:8] | 64 | [{"value": 64.0, "product": "COC1=C(C=CC=C1)C=1N=C2N(CCNC2CCSC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The product from Step 13.f. (2.50 g, 3.96 mmol) was dissolved in CH2Cl2 (16.0 ml) and treated with Tfa (4.0 ml) at room temperature under N2 for about 3.5 hours. The reaction was then poured cautiously into a saturated NaHCO3 solution (150 ml) and the product was extracted with CH2Cl2 (2×50 ml), dried over Na2SO4, filt... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | c1cn2c(n1)C[NH]CC2 | c1cn2c(n1)CNCC2 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1cn2c(n1)CNCC2 | HO- | C(Cl)Cl | null | null | COc1ccccc1-c1cn2c(n1)C(CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)N(C(=O)OC(C)(C)C)CC2>C(Cl)Cl>COc1ccccc1-c1cn2c(n1)C(CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)NCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2f69eb22a73548d49d0fdc2cd160693e | CC(C)(C)OC(=O)N[C@@H](CSC(c1ccccc1)(c1ccccc1)c1ccccc1)C(=O)O.COc1ccccc1-c1cn2c(n1)C(CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)NCC2>>COc1ccccc1-c1cn2c(n1)C(CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)N(C(=O)C(CSC(c1ccccc1)(c1ccccc1)c1ccccc1)NC(=O)OC(C)(C)C)CC2 | N([C@@H](CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C(=O)O)C(=O)OC(C)(C)C.CN1CCOCC1.C1=CC2=C(N=C1)N(N=N2)O.C(CCl)Cl.COC1=C(C=CC=C1)C=1N=C2N(CCNC2CCSC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C1>>CC(C)(OC(=O)NC(C(=O)N1C(C=2N(CC1)C=C(N2)C2=C(C=CC=C2)OC)CCSC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CSC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=C... | O[C:38](=[O:39])[C@H:40]([CH2:41][S:42][C:43]([c:44]1[cH:45][cH:46][cH:47][cH:48][cH:49]1)([c:50]1[cH:51][cH:52][cH:53][cH:54][cH:55]1)[c:56]1[cH:57][cH:58][cH:59][cH:60][cH:61]1)[NH:62][C:63](=[O:64])[O:65][C:66]([CH3:67])([CH3:68])[CH3:69].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][n:11]2[c:12]([n... | CC(C)(C)OC(=O)N[C@@H](CSC(c1ccccc1)(c1ccccc1)c1ccccc1)C(=O)O.COc1ccccc1-c1cn2c(n1)C(CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)NCC2 | COc1ccccc1-c1cn2c(n1)C(CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)N(C(=O)C(CSC(c1ccccc1)(c1ccccc1)c1ccccc1)NC(=O)OC(C)(C)C)CC2 | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 1515c28914c70e186c1937aeeb58be05749758709de3962e3729cd6b7a126c4d | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)N1CCn2cc(-c3ccccc3)nc2C1CCSC(c1ccccc1)(c1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C@@H;D3;+0:3](-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12]-[#16:13].[#7;a:14]:[c:15]1:[#7;a:16]-[C:17]-[C:18]-[NH;D2;+0:19]-[C:20]-1-[C:21]>>[#16:13]-[C:12]-[CH;D3;+0:3](-[#7:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C... | 97 | [{"value": 97.0, "product": "CC(C)(OC(=O)NC(C(=O)N1C(C=2N(CC1)C=C(N2)C2=C(C=CC=C2)OC)CCSC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)CSC(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of the product from Step 13.g. (compound xxi, where R2, R3, R5, R6, and R7 are H, R4 is 2-methoxyphenyl, and n is 1) (1.30 g, 2.45 mmol), Boc-(L)-Cys(Trt)-OH (1.14 g, 2.45 mmol), NMM (270 uL, 2.45 mmol), and HOAt (333 mg, 2.45 mmol) in THF (20 ml) was treated with EDC (470 mg, 2.45 mmol) at room temperature u... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | c1cn2c(n1)CNCC2 | c1cn2c(n1)C[NH]CC2 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1cn2c(n1)C[NH]CC2 | HO- | C1CCOC1 | null | 8 | CC(C)(C)OC(=O)N[C@@H](CSC(c1ccccc1)(c1ccccc1)c1ccccc1)C(=O)O.COc1ccccc1-c1cn2c(n1)C(CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)NCC2>C1CCOC1>COc1ccccc1-c1cn2c(n1)C(CCSC(c1ccccc1)(c1ccccc1)c1ccccc1)N(C(=O)C(CSC(c1ccccc1)(c1ccccc1)c1ccccc1)NC(=O)OC(C)(C)C)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eba8a3d7c9cc40e19409ef56651f619b | BrBr.CC(=O)c1ccccc1Br>>O=C(CBr)c1ccccc1Br | BrBr.BrC1=C(C=CC=C1)C(C)=O>>BrCC(=O)C1=C(C=CC=C1)Br | Br[Br:4].[O:1]=[C:2]([CH3:3])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Br:11]>>[O:1]=[C:2]([CH2:3][Br:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Br:11] | BrBr.CC(=O)c1ccccc1Br | O=C(CBr)c1ccccc1Br | null | null | C(C)(=O)O | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | null | null | Bromine (40.3 g, 0.25 mol) was added dropwise to a solution of 2′-Bromoacetophenone (50.0 g, 0.25 mol) in acetic acid (50 ml) over 1.5 hours at 15–20° C. The solution was then allowed to warm to room temperature and concentrated under reduced pressure to yield a crude product that was used without further purification.... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | C(C)(=O)O | null | null | BrBr.CC(=O)c1ccccc1Br>C(C)(=O)O>O=C(CBr)c1ccccc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed8ebcb207f34f5b8625d6d6eb29354b | CC(=O)OC1O[C@](COC(=O)c2ccccc2)([C@@H](CO)OC(=O)c2ccccc2)[C@H](OCc2ccccc2)[C@H]1OC(C)=O.Cc1c[nH]c(=O)[nH]c1=O>>CC(=O)O[C@H]1[C@H](n2cc(C)c(=O)[nH]c2=O)OC(COC(=O)c2ccccc2)(COC(=O)c2ccccc2)[C@@H]1OCc1ccccc1 | O(S(=O)(=O)C(F)(F)F)[Si](C)(C)C.C(C1=CC=CC=C1)(=O)O[C@@H]([C@@]1([C@@H]([C@H](C(OC(C)=O)O1)OC(C)=O)OCC1=CC=CC=C1)COC(C1=CC=CC=C1)=O)CO.N1C(=O)NC(=O)C(C)=C1.C(O)([O-])=O.[Na+].C/C(=N\[Si](C)(C)C)/O[Si](C)(C)C>>C(C)(=O)O[C@H]1[C@@H](OC([C@@H]1OCC1=CC=CC=C1)(COC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O)N1C(=O)NC(=O)C(C)=C1 | CC(=O)O[CH:6]1[C@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@@H:38]([O:39][CH2:40][c:41]2[cH:42][cH:43][cH:44][cH:45][cH:46]2)[C@@:17]([CH2:18][O:19][C:20](=[O:21])[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)([C@@H:28](CO)[O:29][C:30](=[O:31])[c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[O:16]1.[nH:7]1[cH:8][c:9]([CH3:10])[c:11](... | CC(=O)OC1O[C@](COC(=O)c2ccccc2)([C@@H](CO)OC(=O)c2ccccc2)[C@H](OCc2ccccc2)[C@H]1OC(C)=O.Cc1c[nH]c(=O)[nH]c1=O | CC(=O)O[C@H]1[C@H](n2cc(C)c(=O)[nH]c2=O)OC(COC(=O)c2ccccc2)(COC(=O)c2ccccc2)[C@@H]1OCc1ccccc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | f3f8c550d8457a079e03055f8ab87a709d542381968bdaf4cc2f2b67d5a0bf18 | d99239e46ca50ed49c94c79a936d1a41bb6ca066ecb2eb235c70828e67ae9de8 | O=C(OCC1(COC(=O)c2ccccc2)O[C@@H](n2ccc(=O)[nH]c2=O)C[C@H]1OCc1ccccc1)c1ccccc1 | C-C(=O)-O-[CH;D3;+0:1]1-[#8:2]-[C@;H0;D4;+0:3](-[C:4]-[#8:5]-[C:6]=[O;D1;H0:7])(-[C@@H;D3;+0:8](-C-O)-[#8:9]-[C:10](=[O;D1;H0:11])-[c:12])-[C:13](-[#8:14])-[C:15]-1-[#8:16]-[C:17](-[C;D1;H3:18])=[O;D1;H0:19].[O;D1;H0:20]=[c:21]1:[#7;a:22]:[c:23]:[c:24]:[c:25]:[nH;D2;+0:26]:1>>[#8:14]-[C:13]1-[C:15](-[#8:16]-[C:17](-[C;... | 85 | [{"value": 85.0, "product": "C(C)(=O)O[C@H]1[C@@H](OC([C@@H]1OCC1=CC=CC=C1)(COC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O)N1C(=O)NC(=O)C(C)=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.2, "product": "C(C)(=O)O[C@H]1[C@@H](OC([C@@H]1OCC1=CC=CC=C1)(COC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O)N1C(=O)NC(=O)C(C)=C1"... | 60 | CELSIUS | 1 | HOUR | To a stirred suspension of the anomeric mixture 3 (7.26 g, 0.013 mol) and thymine (3.25 g, 0.028 mol) in anhydrous acetonitrile (80 cm3) was added N,O-bis(trimethylsilyl)acetamide (19.1 cm3, 0.077 mol). The reaction mixture was stirred at 60° C. for 1 h and then cooled to 0° C. Trimethylsilyl triflate (4.1 cm3, 0.023 m... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Primary alcohol | Ester.Ether | C1CCOC1.c1cncnc1 | C1CCOC1.c1cncnc1 | C1CCOC1.c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(C)#N | 60 | 1 | CC(=O)OC1O[C@](COC(=O)c2ccccc2)([C@@H](CO)OC(=O)c2ccccc2)[C@H](OCc2ccccc2)[C@H]1OC(C)=O.Cc1c[nH]c(=O)[nH]c1=O>C(C)#N>CC(=O)O[C@H]1[C@H](n2cc(C)c(=O)[nH]c2=O)OC(COC(=O)c2ccccc2)(COC(=O)c2ccccc2)[C@@H]1OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5bfff2d50122426db511b3e9f2d81ec6 | CC(=O)O[C@H]1[C@H](n2cc(C)c(=O)[nH]c2=O)OC(COC(=O)c2ccccc2)(COC(=O)c2ccccc2)[C@@H]1OCc1ccccc1>>Cc1cn([C@@H]2OC(CO)(CO)[C@H](OCc3ccccc3)[C@H]2O)c(=O)[nH]c1=O | Cl.C(C)(=O)O[C@H]1[C@@H](OC([C@@H]1OCC1=CC=CC=C1)(COC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O)N1C(=O)NC(=O)C(C)=C1.C[O-].[Na+]>>C(C1=CC=CC=C1)O[C@@H]1[C@H]([C@@H](OC1(CO)CO)N1C(=O)NC(=O)C(C)=C1)O | CC(=O)[O:22][C@H:21]1[C@H:5]([n:4]2[cH:3][c:2]([CH3:1])[c:26](=[O:27])[nH:25][c:23]2=[O:24])[O:6][C:7]([CH2:8][O:9]C(=O)c2ccccc2)([CH2:10][O:11]C(=O)c2ccccc2)[C@@H:12]1[O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][c:2]1[cH:3][n:4]([C@@H:5]2[O:6][C:7]([CH2:8][OH:9])([CH2:10][OH:11])[C@H:12]([O:13][C... | CC(=O)O[C@H]1[C@H](n2cc(C)c(=O)[nH]c2=O)OC(COC(=O)c2ccccc2)(COC(=O)c2ccccc2)[C@@H]1OCc1ccccc1 | Cc1cn([C@@H]2OC(CO)(CO)[C@H](OCc3ccccc3)[C@H]2O)c(=O)[nH]c1=O | null | null | CO | Reduction | OtherReaction | 54b73b3c3d2295db61c7b82e0c48a84cdf0fff52c09808651452c3f5b5703cf0 | 862d22c00dba0369fa5bd9dacdeb4ed88b794a9b4815067d1c260dcbd3122add | O=c1ccn([C@H]2C[C@@H](OCc3ccccc3)CO2)c(=O)[nH]1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[C:4](-[C:5]-[O;H0;D2;+0:6]-C(=O)-c2:c:c:c:c:c:2)(-[C:7]-[O;H0;D2;+0:8]-C(=O)-c2:c:c:c:c:c:2)-[#8:9]-[C:10]-1>>[OH;D1;+0:6]-[C:5]-[C:4]1(-[C:7]-[OH;D1;+0:8])-[#8:9]-[C:10]-[C:2](-[OH;D1;+0:1])-[C:3]-1 | 91 | [{"value": 89.0, "product": "C(C1=CC=CC=C1)O[C@@H]1[C@H]([C@@H](OC1(CO)CO)N1C(=O)NC(=O)C(C)=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.0, "product": "C(C1=CC=CC=C1)O[C@@H]1[C@H]([C@@H](OC1(CO)CO)N1C(=O)NC(=O)C(C)=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a stirred solution of nucleoside 4 (9.00 g, 0.014 mol) in methanol (130 cm3) was added sodium methoxide (3.87 g, 0.0716 mol). The reaction mixture was stirred at room temperature for 4 h and then neutralised with dilute hydrochloric acid. The mixture was evaporated to dryness under reduced pressure followed by coeva... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Primary alcohol.Primary alcohol.Secondary alcohol | c1ccccc1.c1ccccc1 | null | c1cncnc1.C1CCOC1.c1ccccc1 | HO- | CO | null | 4 | CC(=O)O[C@H]1[C@H](n2cc(C)c(=O)[nH]c2=O)OC(COC(=O)c2ccccc2)(COC(=O)c2ccccc2)[C@@H]1OCc1ccccc1>CO>Cc1cn([C@@H]2OC(CO)(CO)[C@H](OCc3ccccc3)[C@H]2O)c(=O)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e288918a92354e2f82ef20876e9c4e95 | COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1.Cc1ccc(S(=O)(=O)OC[C@]2(CO)O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](O)[C@H]2OCc2ccccc2)cc1>>COc1ccc(C(OC[C@@]2(COS(=O)(=O)c3ccc(C)cc3)O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](O)[C@H]2OCc2ccccc2)(c2ccccc2)c2ccc(OC)cc2)cc1 | COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)Cl)C=C1.C(C1=CC=CC=C1)O[C@@H]1[C@H]([C@@H](O[C@@]1(CO)COS(=O)(=O)C1=CC=C(C=C1)C)N1C(=O)NC(=O)C(C)=C1)O.COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)Cl)C=C1>>C(C1=CC=CC=C1)O[C@@H]1[C@H]([C@@H](O[C@@]1(COC(C1=CC=C(C=C1)OC)(C1=CC=C(C=C1)OC)C1=CC=CC=C1)COS(=O)(=O)C1=CC=C(C=C1)C)N1C(=O)N... | Cl[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:60][cH:59]1)([c:45]1[cH:46][cH:47][cH:48][cH:49][cH:50]1)[c:51]1[cH:52][cH:53][c:54]([O:55][CH3:56])[cH:57][cH:58]1.[OH:8][CH2:9][C@@:10]1([CH2:11][O:12][S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][c:19]([CH3:20])[cH:21][cH:22]2)[O:23][C@@H:24]([n:25]2[cH:26][c:27]([CH3... | COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1.Cc1ccc(S(=O)(=O)OC[C@]2(CO)O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](O)[C@H]2OCc2ccccc2)cc1 | COc1ccc(C(OC[C@@]2(COS(=O)(=O)c3ccc(C)cc3)O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](O)[C@H]2OCc2ccccc2)(c2ccccc2)c2ccc(OC)cc2)cc1 | null | null | ClCCl.N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | fb955127af596450632db904a0236d35e158107f202af7adbe96e225ff5ada1f | 5adfb0e9c2ca3c5afac2c4b206fb6fda83b92f44074f2a75e26f913c192bc169 | O=c1ccn([C@H]2C[C@@H](OCc3ccccc3)[C@](COC(c3ccccc3)(c3ccccc3)c3ccccc3)(COS(=O)(=O)c3ccccc3)O2)c(=O)[nH]1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[#8:11]-[C:12]-[C:13]-[OH;D1;+0:14]>>[#8:11]-[C:12]-[C:13]-[O;H0;D2;+0:14]-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10] | 75 | [{"value": 75.0, "product": "C(C1=CC=CC=C1)O[C@@H]1[C@H]([C@@H](O[C@@]1(COC(C1=CC=C(C=C1)OC)(C1=CC=C(C=C1)OC)C1=CC=CC=C1)COS(=O)(=O)C1=CC=C(C=C1)C)N1C(=O)NC(=O)C(C)=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.5, "product": "C(C1=CC=CC=C1)O[C@@H]1[C@H]([C@@H](O[C@@]1(COC(C1=CC=C(C=C1)OC)(C1=CC=C... | null | null | 23 | HOUR | To a solution of nucleoside 6 (3.66 g, 6.88 mmol) in anhydrous pyridine (25 cm3) was added N,N-(dimethylamino)pyridine (0.84 g, 6.81 mmol) and 4,4′-dimethoxytrityl chloride (3.5 g, 13.2 mmol) and the mixture was stirred for 23 h at room temperature. Additional N,N-(dimethylamino)pyridine (0.250 g, 2.06 mmol) and 4,4′-d... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Primary alcohol | Ether | null | null | c1ccccc1.c1ccccc1.C1CCOC1.c1cncnc1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | ClCCl.N1=CC=CC=C1 | null | 23 | COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1.Cc1ccc(S(=O)(=O)OC[C@]2(CO)O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](O)[C@H]2OCc2ccccc2)cc1>ClCCl.N1=CC=CC=C1>COc1ccc(C(OC[C@@]2(COS(=O)(=O)c3ccc(C)cc3)O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](O)[C@H]2OCc2ccccc2)(c2ccccc2)c2ccc(OC)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a56ae67280a44f09cf792935a32deac | COc1ccc(C(OC[C@@]2(COS(=O)(=O)c3ccc(C)cc3)O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](O)[C@H]2OCc2ccccc2)(c2ccccc2)c2ccc(OC)cc2)cc1>>COc1ccc(C(OC[C@@]23CO[C@@H]([C@H](n4cc(C)c(=O)[nH]c4=O)O2)[C@H]3OCc2ccccc2)(c2ccccc2)c2ccc(OC)cc2)cc1 | ClCCl.C(O)([O-])=O.[Na+].C(C1=CC=CC=C1)O[C@@H]1[C@H]([C@@H](O[C@@]1(COC(C1=CC=C(C=C1)OC)(C1=CC=C(C=C1)OC)C1=CC=CC=C1)COS(=O)(=O)C1=CC=C(C=C1)C)N1C(=O)NC(=O)C(C)=C1)O.[H-].[Na+]>>C(C1=CC=CC=C1)O[C@H]1[C@]2(O[C@H]([C@@H]1OC2)N2C(=O)NC(=O)C(C)=C2)COC(C2=CC=C(C=C2)OC)(C2=CC=C(C=C2)OC)C2=CC=CC=C2 | Cc1ccc(S(=O)(=O)O[CH2:11][C@:10]2([CH2:9][O:8][C:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:49][cH:48]3)([c:34]3[cH:35][cH:36][cH:37][cH:38][cH:39]3)[c:40]3[cH:41][cH:42][c:43]([O:44][CH3:45])[cH:46][cH:47]3)[O:24][C@@H:14]([n:15]3[cH:16][c:17]([CH3:18])[c:19](=[O:20])[nH:21][c:22]3=[O:23])[C@H:13]([OH:12])[C@H:25]2[O... | COc1ccc(C(OC[C@@]2(COS(=O)(=O)c3ccc(C)cc3)O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](O)[C@H]2OCc2ccccc2)(c2ccccc2)c2ccc(OC)cc2)cc1 | COc1ccc(C(OC[C@@]23CO[C@@H]([C@H](n4cc(C)c(=O)[nH]c4=O)O2)[C@H]3OCc2ccccc2)(c2ccccc2)c2ccc(OC)cc2)cc1 | null | null | ClCCl.N1=CC=CC=C1.CN(C)C=O | Functional Group Interconversion | OtherReaction | 331430e1936e5695ba0860df10c92abe96a5c4020bc39c94c83a32f8a869bb80 | e9acbe4f8945dd1c4846cdd0e6082949a2428f00ae9db5a7480dd333e0e948f6 | O=c1ccn([C@@H]2O[C@@]3(COC(c4ccccc4)(c4ccccc4)c4ccccc4)CO[C@@H]2[C@H]3OCc2ccccc2)c(=O)[nH]1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]2(-[C:3])-[#8:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-2):c:c:1>>[C:3]-[C:2]12-[#8:4]-[C:5]-[C:6](-[C:8]-1)-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-2 | 96 | [{"value": 96.0, "product": "C(C1=CC=CC=C1)O[C@H]1[C@]2(O[C@H]([C@@H]1OC2)N2C(=O)NC(=O)C(C)=C2)COC(C2=CC=C(C=C2)OC)(C2=CC=C(C=C2)OC)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.4, "product": "C(C1=CC=CC=C1)O[C@H]1[C@]2(O[C@H]([C@@H]1OC2)N2C(=O)NC(=O)C(C)=C2)COC(C2=CC=C(C=C2)OC)(C2=CC=C(C=... | null | null | 25 | HOUR | To a solution of nucleoside 7 (4.22 g, 5.06 mmol) in anhydrous DMF (25 cm3) at 0° C. was added a 60% suspension of sodium hydride in mineral oil (w/w, 0.607 g, 1 5.7 mmol, added in four portions during 20 min) and the reaction mixture was stirred at room temperature for 25 h, cooled to 0° C. and diluted with dichlorome... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary alcohol | Ether | c1ccccc1 | C1O[C@H]2CO[C@H]1C2 | c1ccccc1.c1cncnc1.C1O[C@H]2CO[C@H]1C2.c1ccccc1.c1ccccc1.c1ccccc1 | TsOH.HO- | ClCCl.N1=CC=CC=C1.CN(C)C=O | null | 25 | COc1ccc(C(OC[C@@]2(COS(=O)(=O)c3ccc(C)cc3)O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](O)[C@H]2OCc2ccccc2)(c2ccccc2)c2ccc(OC)cc2)cc1>ClCCl.N1=CC=CC=C1.CN(C)C=O>COc1ccc(C(OC[C@@]23CO[C@@H]([C@H](n4cc(C)c(=O)[nH]c4=O)O2)[C@H]3OCc2ccccc2)(c2ccccc2)c2ccc(OC)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d941bde6761f4c328e8182f61055248b | COc1ccc(C(OC[C@@]23CO[C@@H]([C@H](n4cc(C)c(=O)[nH]c4=O)O2)[C@H]3OCc2ccccc2)(c2ccccc2)c2ccc(OC)cc2)cc1>>Cc1cn([C@@H]2O[C@@]3(CO)CO[C@@H]2[C@H]3O)c(=O)[nH]c1=O | C(C1=CC=CC=C1)O[C@H]1[C@]2(O[C@H]([C@@H]1OC2)N2C(=O)NC(=O)C(C)=C2)COC(C2=CC=C(C=C2)OC)(C2=CC=C(C=C2)OC)C2=CC=CC=C2>>O[C@H]1[C@]2(O[C@H]([C@@H]1OC2)N2C(=O)NC(=O)C(C)=C2)CO | COc1ccc(C(c2ccccc2)(c2ccc(OC)cc2)[O:9][CH2:8][C@:7]23[O:6][C@@H:5]([n:4]4[cH:3][c:2]([CH3:1])[c:18](=[O:19])[nH:17][c:15]4=[O:16])[C@H:12]([O:11][CH2:10]2)[C@H:13]3[O:14]Cc2ccccc2)cc1>>[CH3:1][c:2]1[cH:3][n:4]([C@@H:5]2[O:6][C@@:7]3([CH2:8][OH:9])[CH2:10][O:11][C@@H:12]2[C@H:13]3[OH:14])[c:15](=[O:16])[nH:17][c:18]1=[O... | COc1ccc(C(OC[C@@]23CO[C@@H]([C@H](n4cc(C)c(=O)[nH]c4=O)O2)[C@H]3OCc2ccccc2)(c2ccccc2)c2ccc(OC)cc2)cc1 | Cc1cn([C@@H]2O[C@@]3(CO)CO[C@@H]2[C@H]3O)c(=O)[nH]c1=O | null | [Pd] | CO | Reduction | OtherReaction | 584eab506ca4e9902fea84d81c320c35e85be77e7de7d9b80b0faed80654feed | 3881adf5a34b953060aef15713af994a062be50065fcd27b05641cb71c6511f2 | O=c1ccn([C@@H]2OC3CO[C@@H]2C3)c(=O)[nH]1 | C-O-c1:c:c:c(-C(-[O;H0;D2;+0:1]-[C:2]-[C:3](-[#8:4])-[C:5](-[O;H0;D2;+0:6]-C-c2:c:c:c:c:c:2)-[C:7]-[#8:8])(-c2:c:c:c:c:c:2)-c2:c:c:c(-O-C):c:c:2):c:c:1>>[#8:8]-[C:7]-[C:5](-[OH;D1;+0:6])-[C:3](-[C:2]-[OH;D1;+0:1])-[#8:4] | 82 | [{"value": 82.0, "product": "O[C@H]1[C@]2(O[C@H]([C@@H]1OC2)N2C(=O)NC(=O)C(C)=C2)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.8, "product": "O[C@H]1[C@]2(O[C@H]([C@@H]1OC2)N2C(=O)NC(=O)C(C)=C2)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 26 | HOUR | Nucleoside 8 (3.09 g, 4.66 mmol) was dissolved in methanol (40 cm3) and 10% palladium on carbon (3 g, suspended in methanol (20 cm3)) was added. The mixture was degassed and stirred under an atmosphere of hydrogen. After 26 h, the mixture was filtered (silica gel, washed with dichloromethane/methanol (700 cm3; 1:3, v/v... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Primary alcohol.Secondary alcohol | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | C1O[C@H]2CO[C@@H]1C2.c1cncnc1 | HO- | [Pd].CO | null | 26 | COc1ccc(C(OC[C@@]23CO[C@@H]([C@H](n4cc(C)c(=O)[nH]c4=O)O2)[C@H]3OCc2ccccc2)(c2ccccc2)c2ccc(OC)cc2)cc1>[Pd].CO>Cc1cn([C@@H]2O[C@@]3(CO)CO[C@@H]2[C@H]3O)c(=O)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f85f96ac167340d3b6eec326e09ec856 | COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1.Cc1cn([C@@H]2O[C@@]3(CO)CO[C@@H]2[C@H]3O)c(=O)[nH]c1=O>>COc1ccc(C(OC[C@@]23CO[C@@H]([C@H](n4cc(C)c(=O)[nH]c4=O)O2)[C@H]3O)(c2ccccc2)c2ccc(OC)cc2)cc1 | C(O)([O-])=O.[Na+].COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)Cl)C=C1.O[C@H]1[C@]2(O[C@H]([C@@H]1OC2)N2C(=O)NC(=O)C(C)=C2)CO.COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)Cl)C=C1>>COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)OC[C@]23O[C@H]([C@H](OC2)[C@H]3O)N3C(=O)NC(=O)C(C)=C3)C=C1 | Cl[C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:42][cH:41]1)([c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1)[c:33]1[cH:34][cH:35][c:36]([O:37][CH3:38])[cH:39][cH:40]1.[OH:8][CH2:9][C@@:10]12[CH2:11][O:12][C@@H:13]([C@H:14]([n:15]3[cH:16][c:17]([CH3:18])[c:19](=[O:20])[nH:21][c:22]3=[O:23])[O:24]1)[C@H:25]2[OH:26]>>[CH3:1... | COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1.Cc1cn([C@@H]2O[C@@]3(CO)CO[C@@H]2[C@H]3O)c(=O)[nH]c1=O | COc1ccc(C(OC[C@@]23CO[C@@H]([C@H](n4cc(C)c(=O)[nH]c4=O)O2)[C@H]3O)(c2ccccc2)c2ccc(OC)cc2)cc1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | fb955127af596450632db904a0236d35e158107f202af7adbe96e225ff5ada1f | 5adfb0e9c2ca3c5afac2c4b206fb6fda83b92f44074f2a75e26f913c192bc169 | O=c1ccn([C@@H]2O[C@@]3(COC(c4ccccc4)(c4ccccc4)c4ccccc4)CO[C@@H]2C3)c(=O)[nH]1 | Cl-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10].[#8:11]-[C:12]-[C:13]-[OH;D1;+0:14]>>[#8:11]-[C:12]-[C:13]-[O;H0;D2;+0:14]-[C;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[c:8](:[c:9]):[c:10] | 50 | [{"value": 50.0, "product": "COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)OC[C@]23O[C@H]([C@H](OC2)[C@H]3O)N3C(=O)NC(=O)C(C)=C3)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.0, "product": "COC1=CC=C(C(C2=CC=C(C=C2)OC)(C2=CC=CC=C2)OC[C@]23O[C@H]([C@H](OC2)[C@H]3O)N3C(=O)NC(=O)C(C)=C3)C=C1", "details":... | null | null | 21 | HOUR | To a stirred solution of nucleoside 9 (0.500 g, 1.85 mmol) in anhydrous pyridine (10 cm3) was added 4,4′-dimethoxytrityl chloride (0.941 g, 2.78 mmol) and the mixture was stirred for 25 h at room temperature for 25 h after which additional 4,4′-dimethoxytrityl chloride (0.062 g, 0.18 mmol) was added and stirring at roo... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Primary alcohol | Ether | null | null | C1O[C@H]2CO[C@H]1C2.c1ccccc1.c1cncnc1.c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | 21 | COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1.Cc1cn([C@@H]2O[C@@]3(CO)CO[C@@H]2[C@H]3O)c(=O)[nH]c1=O>N1=CC=CC=C1>COc1ccc(C(OC[C@@]23CO[C@@H]([C@H](n4cc(C)c(=O)[nH]c4=O)O2)[C@H]3O)(c2ccccc2)c2ccc(OC)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bdb07b42465b49e18d261ab22f0fce69 | CC(=O)OC1O[C@H]([C@@H](COC(=O)c2ccccc2)OCc2ccccc2)[C@@H](OCc2ccccc2)[C@H]1OC(C)=O.Cc1c[nH]c(=O)[nH]c1=O>>CC(=O)O[C@@H]1[C@H](OCc2ccccc2)[C@@H]([C@@H](COC(=O)c2ccccc2)OCc2ccccc2)O[C@H]1n1cc(C)c(=O)[nH]c1=O | C(O)([O-])=O.[Na+].C(C1=CC=CC=C1)(=O)OC[C@H]([C@@H]1[C@H]([C@H](C(OC(C)=O)O1)OC(C)=O)OCC1=CC=CC=C1)OCC1=CC=CC=C1.N1C(=O)NC(=O)C(C)=C1.O(S(=O)(=O)C(F)(F)F)[Si](C)(C)C>>C(C)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OCC1=CC=CC=C1)[C@H](OCC1=CC=CC=C1)COC(C1=CC=CC=C1)=O)N1C(=O)NC(=O)C(C)=C1 | CC(=O)O[CH:36]1[C@H:5]([O:4][C:2]([CH3:1])=[O:3])[C@H:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[C@@H:15]([C@@H:16]([CH2:17][O:18][C:19](=[O:20])[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[O:27][CH2:28][c:29]2[cH:30][cH:31][cH:32][cH:33][cH:34]2)[O:35]1.[nH:37]1[cH:38][c:39]([CH3:40])[c:41](=[O:42])[nH... | CC(=O)OC1O[C@H]([C@@H](COC(=O)c2ccccc2)OCc2ccccc2)[C@@H](OCc2ccccc2)[C@H]1OC(C)=O.Cc1c[nH]c(=O)[nH]c1=O | CC(=O)O[C@@H]1[C@H](OCc2ccccc2)[C@@H]([C@@H](COC(=O)c2ccccc2)OCc2ccccc2)O[C@H]1n1cc(C)c(=O)[nH]c1=O | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | f2636d20486b010c17ffd1989b837170c56e2ee0cfd7dfedf42269b47714189b | 555d70919b361b350c80f46e885ff5cda87616c212c907f1056db36bb1eb2375 | O=C(OC[C@@H](OCc1ccccc1)[C@H]1O[C@@H](n2ccc(=O)[nH]c2=O)C[C@@H]1OCc1ccccc1)c1ccccc1 | C-C(=O)-O-[CH;D3;+0:1]1-[#8:2]-[C:3]-[C:4]-[C:5]-1-[#8:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9].[O;D1;H0:10]=[c:11]1:[#7;a:12]:[c:13]:[c:14]:[c:15]:[nH;D2;+0:16]:1>>[C;D1;H3:8]-[C:7](=[O;D1;H0:9])-[#8:6]-[C:5]1-[C:4]-[C:3]-[#8:2]-[C@H;D3;+0:1]-1-[n;H0;D3;+0:16]1:[c:15]:[c:14]:[c:13]:[#7;a:12]:[c:11]:1=[O;D1;H0:10] | 81 | [{"value": 81.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1 | HOUR | To a stirred suspension of the anomeric mixture 14 (4.50 g, 8.21 mmol) and thymine (1.55 g, 12.31 mmol) in anhydrous acetonitrile (50 cm3) was added N,O-bis(trimethylsilyl)-acetamide (12.2 cm3, 49.3 mmol). The reaction mixture was stirred at 60° C. for 1 h and then cooled to 0° C. Trimethylsilyl triflate (2.97 cm3, 16.... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Ether | C1CCOC1.c1cncnc1 | C1CCOC1.c1cncnc1 | C1CCOC1.c1ccccc1.c1ccccc1.c1ccccc1.c1cncnc1 | HO- | C(C)#N | 60 | 1 | CC(=O)OC1O[C@H]([C@@H](COC(=O)c2ccccc2)OCc2ccccc2)[C@@H](OCc2ccccc2)[C@H]1OC(C)=O.Cc1c[nH]c(=O)[nH]c1=O>C(C)#N>CC(=O)O[C@@H]1[C@H](OCc2ccccc2)[C@@H]([C@@H](COC(=O)c2ccccc2)OCc2ccccc2)O[C@H]1n1cc(C)c(=O)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a99ac7b5da104cf58c343a9f780e764c | CC(=O)O[C@@H]1[C@H](OCc2ccccc2)[C@@H]([C@@H](COC(=O)c2ccccc2)OCc2ccccc2)O[C@H]1n1cc(C)c(=O)[nH]c1=O>>Cc1cn([C@@H]2O[C@H]([C@@H](CO)OCc3ccccc3)[C@@H](OCc3ccccc3)[C@H]2O)c(=O)[nH]c1=O | Cl.C(C)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OCC1=CC=CC=C1)[C@H](OCC1=CC=CC=C1)COC(C1=CC=CC=C1)=O)N1C(=O)NC(=O)C(C)=C1.C[O-].[Na+]>>C(C1=CC=CC=C1)O[C@H]1[C@H]([C@@H](O[C@@H]1[C@H](OCC1=CC=CC=C1)CO)N1C(=O)NC(=O)C(C)=C1)O | CC(=O)[O:29][C@H:28]1[C@H:5]([n:4]2[cH:3][c:2]([CH3:1])[c:33](=[O:34])[nH:32][c:30]2=[O:31])[O:6][C@H:7]([C@@H:8]([CH2:9][O:10]C(=O)c2ccccc2)[O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[C@H:19]1[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][c:2]1[cH:3][n:4]([C@@H:5]2[O:6][C@H:7]([C@@H:... | CC(=O)O[C@@H]1[C@H](OCc2ccccc2)[C@@H]([C@@H](COC(=O)c2ccccc2)OCc2ccccc2)O[C@H]1n1cc(C)c(=O)[nH]c1=O | Cc1cn([C@@H]2O[C@H]([C@@H](CO)OCc3ccccc3)[C@@H](OCc3ccccc3)[C@H]2O)c(=O)[nH]c1=O | null | null | CO | Reduction | OtherReaction | 6a18b7832afe994c2d9732498b0a23dd5121cfbb369dca00e8b5c0bfc25feea4 | f7eaf12d8ca7f7f33975963ce6d5d64e20763721d3f59f4cd8cae1a62b7f8497 | O=c1ccn([C@H]2C[C@H](OCc3ccccc3)[C@@H](COCc3ccccc3)O2)c(=O)[nH]1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#8:5].O=C(-[O;H0;D2;+0:6]-[C:7]-[C:8])-c1:c:c:c:c:c:1>>[#8:5]-[C:4]-[C:2](-[OH;D1;+0:1])-[C:3].[C:8]-[C:7]-[OH;D1;+0:6] | 88 | [{"value": 88.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | To a stirred solution of nucleoside 15 (3.00 g, 4.88 mmol) in methanol (50 cm3) was added sodium methoxide (0.79 g, 14.7 mmol). The reaction mixture was stirred for 14 h at room temperature and subsequently neutralised with dilute hydrochloric acid (5 cm3) whereupon ice-cold H2O (50 cm3) was added. The resulting mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Primary alcohol.Secondary alcohol | c1ccccc1 | null | c1cncnc1.C1CCOC1.c1ccccc1.c1ccccc1 | HO- | CO | null | 14 | CC(=O)O[C@@H]1[C@H](OCc2ccccc2)[C@@H]([C@@H](COC(=O)c2ccccc2)OCc2ccccc2)O[C@H]1n1cc(C)c(=O)[nH]c1=O>CO>Cc1cn([C@@H]2O[C@H]([C@@H](CO)OCc3ccccc3)[C@@H](OCc3ccccc3)[C@H]2O)c(=O)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-82b1b1af80764c67a36be49bb71bad5a | Cc1ccc(S(=O)(=O)Cl)cc1.Cc1cn([C@@H]2O[C@H]([C@@H](CO)OCc3ccccc3)[C@@H](OCc3ccccc3)[C@H]2O)c(=O)[nH]c1=O>>Cc1ccc(S(=O)(=O)OC[C@@H](OCc2ccccc2)[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](OS(=O)(=O)c3ccc(C)cc3)[C@@H]2OCc2ccccc2)cc1 | C(C1=CC=CC=C1)O[C@H]1[C@H]([C@@H](O[C@@H]1[C@H](OCC1=CC=CC=C1)CO)N1C(=O)NC(=O)C(C)=C1)O.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>C(C1=CC=CC=C1)O[C@H]1[C@H]([C@@H](O[C@@H]1[C@H](OCC1=CC=CC=C1)COS(=O)(=O)C1=CC=C(C=C1)C)N1C(=O)NC(=O)C(C)=C1)OS(=O)(=O)C1=CC=C(C=C1)C | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:54][cH:53]1)(=[O:7])=[O:8].[OH:9][CH2:10][C@@H:11]([O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[C@H:20]1[O:21][C@@H:22]([n:23]2[cH:24][c:25]([CH3:26])[c:27](=[O:28])[nH:29][c:30]2=[O:31])[C@H:32]([OH:33])[C@@H:44]1[O:45][CH2:46][c:47]1[cH:48][cH:37][cH:50][cH:51... | Cc1ccc(S(=O)(=O)Cl)cc1.Cc1cn([C@@H]2O[C@H]([C@@H](CO)OCc3ccccc3)[C@@H](OCc3ccccc3)[C@H]2O)c(=O)[nH]c1=O | Cc1ccc(S(=O)(=O)OC[C@@H](OCc2ccccc2)[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](OS(=O)(=O)c3ccc(C)cc3)[C@@H]2OCc2ccccc2)cc1 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | 42f7447215c45d28e2492ff8d5f5645367939cbe923c51b4ebf042c0e52e9e88 | ca0d6434ade0af19dc410836ea26fb3da252c834dc57cd6238ff02698f0a0c53 | O=c1ccn([C@@H]2O[C@H]([C@@H](COS(=O)(=O)c3ccccc3)OCc3ccccc3)[C@@H](OCc3ccccc3)[C@H]2OS(=O)(=O)c2ccccc2)c(=O)[nH]1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#8:7]-[C:8]-[C:9](-[OH;D1;+0:10])-[C:11].[C:12]-[C:13]-[OH;D1;+0:14].[C:15]-[c:16]1:[c:17]:[c:18]:[cH;D2;+0:19]:[cH;D2;+0:20]:[cH;D2;+0:21]:1>>[#8:7]-[C:8]-[C:9](-[O;H0;D2;+0:10]-[#16:22](=[O;D1;H0:23])(=[O;D1;H0:24])-[c;H0;D3;+0:20](:[c:25]:[c:26]):[c:... | 71 | [{"value": 71.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a stirred solution of nucleoside 16 (0.60 g, 1.28 mmol) in dichloromethane (70 cm3) at room temperature was added 4—N,N-(dimethylamino)pyridine (0.63g, 5.12 mmol) and p-toluenesulphonyl chloride (0.73 g, 3.84 mmol). After stirring for 3 h, ice-cold H2O (50 cm3) was added and extraction was performed using dichlorome... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Secondary alcohol.Sulfonyl halide | Tosylate.Tosylate | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.C1CCOC1.c1cncnc1.c1ccccc1.c1ccccc1 | null | ClCCl | null | 3 | Cc1ccc(S(=O)(=O)Cl)cc1.Cc1cn([C@@H]2O[C@H]([C@@H](CO)OCc3ccccc3)[C@@H](OCc3ccccc3)[C@H]2O)c(=O)[nH]c1=O>ClCCl>Cc1ccc(S(=O)(=O)OC[C@@H](OCc2ccccc2)[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](OS(=O)(=O)c3ccc(C)cc3)[C@@H]2OCc2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ecd940dc36e2454898ef625089e089bf | Cc1ccc(S(=O)(=O)OC[C@@H](OCc2ccccc2)[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](OS(=O)(=O)c3ccc(C)cc3)[C@@H]2OCc2ccccc2)cc1>>Cc1cn([C@@H]2O[C@H]3[C@@H](OCc4ccccc4)[C@@H]2OC[C@H]3OCc2ccccc2)c(=O)[nH]c1=O | Cl.[OH-].[Na+].C(C1=CC=CC=C1)O[C@H]1[C@H]([C@@H](O[C@@H]1[C@H](OCC1=CC=CC=C1)COS(=O)(=O)C1=CC=C(C=C1)C)N1C(=O)NC(=O)C(C)=C1)OS(=O)(=O)C1=CC=C(C=C1)C>>C(C1=CC=CC=C1)O[C@@H]1CO[C@@H]2[C@@H](O[C@H]1[C@H]2OCC2=CC=CC=C2)N2C(=O)NC(=O)C(C)=C2 | Cc1ccc(S(=O)(=O)O[C@H:17]2[C@H:5]([n:4]3[cH:3][c:2]([CH3:1])[c:32](=[O:33])[nH:31][c:29]3=[O:30])[O:6][C@H:7]([C@@H:20]([CH2:19][O:18]S(=O)(=O)c3ccc(C)cc3)[O:21][CH2:22][c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[C@H:8]2[O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)cc1>>[CH3:1][c:2]1[cH:3][n:4]([C@@H:5]2[O:... | Cc1ccc(S(=O)(=O)OC[C@@H](OCc2ccccc2)[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](OS(=O)(=O)c3ccc(C)cc3)[C@@H]2OCc2ccccc2)cc1 | Cc1cn([C@@H]2O[C@H]3[C@@H](OCc4ccccc4)[C@@H]2OC[C@H]3OCc2ccccc2)c(=O)[nH]c1=O | null | null | O.C(C)O | Functional Group Interconversion | OtherReaction | f0f096ff2057950c14a91a53c5ca9ea92813030bd2d0c62ee6df58496f620405 | 1483287add64469d2d41bff043a4d777ac42773fb66c8f24d5d17fa78208c16f | O=c1ccn([C@@H]2O[C@H]3[C@@H](OCc4ccccc4)[C@@H]2OC[C@H]3OCc2ccccc2)c(=O)[nH]1 | C-c1:c:c:c(-S(=O)(=O)-O-[C@H;D3;+0:1]2-[C:2](-[#7;a:3])-[#8:4]-[C:5](-[C:6]-[C:7]-[O;H0;D2;+0:8]-S(=O)(=O)-c3:c:c:c(-C):c:c:3)-[C:9]-2-[#8:10]):c:c:1>>[#7;a:3]-[C:2]1-[#8:4]-[C:5]2-[C:6]-[C:7]-[O;H0;D2;+0:8]-[C@H;D3;+0:1]-1-[C:9]-2-[#8:10] | 93 | [{"value": 93.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of nucleoside 17 (0.63 g, 0.81 mmol) in a mixture of ethanol and H2O (40 cm3, 1:1, v/v) at room temperature was added an aqueous solution of sodium hydroxide (1M, 7 cm3). The resulting mixture was heated under reflux for 16 h and then neutralised by addition of dilute hydrochloric acid (10 cm3). T... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Tosylate | Ether | c1ccccc1.C1CCOC1.c1ccccc1 | C1C[C@@H]2C[C@@H](CO2)O1 | c1cncnc1.c1ccccc1.C1C[C@@H]2C[C@@H](CO2)O1.c1ccccc1 | TsOH.HO- | O.C(C)O | null | null | Cc1ccc(S(=O)(=O)OC[C@@H](OCc2ccccc2)[C@H]2O[C@@H](n3cc(C)c(=O)[nH]c3=O)[C@H](OS(=O)(=O)c3ccc(C)cc3)[C@@H]2OCc2ccccc2)cc1>O.C(C)O>Cc1cn([C@@H]2O[C@H]3[C@@H](OCc4ccccc4)[C@@H]2OC[C@H]3OCc2ccccc2)c(=O)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b818d872f7424cc0b8956ae887e47d40 | Cc1cn([C@@H]2O[C@H]3[C@@H](OCc4ccccc4)[C@@H]2OC[C@H]3OCc2ccccc2)c(=O)[nH]c1=O>>Cc1cn([C@@H]2O[C@H]3[C@@H](O)[C@@H]2OC[C@H]3O)c(=O)[nH]c1=O | C(C1=CC=CC=C1)O[C@@H]1CO[C@@H]2[C@@H](O[C@H]1[C@H]2OCC2=CC=CC=C2)N2C(=O)NC(=O)C(C)=C2>>O[C@@H]1CO[C@@H]2[C@@H](O[C@H]1[C@H]2O)N2C(=O)NC(=O)C(C)=C2 | c1ccc(C[O:9][C@@H:8]2[C@@H:7]3[O:6][C@@H:5]([n:4]4[cH:3][c:2]([CH3:1])[c:18](=[O:19])[nH:17][c:15]4=[O:16])[C@H:10]2[O:11][CH2:12][C@H:13]3[O:14]Cc2ccccc2)cc1>>[CH3:1][c:2]1[cH:3][n:4]([C@@H:5]2[O:6][C@H:7]3[C@@H:8]([OH:9])[C@@H:10]2[O:11][CH2:12][C@H:13]3[OH:14])[c:15](=[O:16])[nH:17][c:18]1=[O:19] | Cc1cn([C@@H]2O[C@H]3[C@@H](OCc4ccccc4)[C@@H]2OC[C@H]3OCc2ccccc2)c(=O)[nH]c1=O | Cc1cn([C@@H]2O[C@H]3[C@@H](O)[C@@H]2OC[C@H]3O)c(=O)[nH]c1=O | null | [OH-].[OH-].[Pd+2] | C(C)O | Deprotection | OtherReaction | 3fe27ec170a80ca61e6080b0db8318fb5028033787aa0698b093689be5a0e0e2 | 3cb0396ca8ad36859ee8d51a67a558871ec1b96bb69d5cbac40dafd7041336b3 | O=c1ccn([C@@H]2O[C@@H]3CCO[C@H]2C3)c(=O)[nH]1 | [#8:1]-[C:2]1-[C:3](-[O;H0;D2;+0:4]-C-c2:c:c:c:c:c:2)-[C:5]-[#8:6]-[C:7]-[C:8]-1-[O;H0;D2;+0:9]-C-c1:c:c:c:c:c:1>>[#8:1]-[C:2]1-[C:3](-[OH;D1;+0:4])-[C:5]-[#8:6]-[C:7]-[C:8]-1-[OH;D1;+0:9] | 98 | [{"value": 98.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 26 | HOUR | Nucleoside 18 (0.27 g, 0.60 mmol) was dissolved in absolute ethanol (20 cm3) and 20% palladium hydroxide on carbon (0.25 g) was added. The mixture was degassed and placed under an atmosphere of hydrogen. After stirring for 26 h the catalyst was filtered off (silica gel, washed with methanol, 400 cm3) and the filtrate w... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Secondary alcohol.Secondary alcohol | c1ccccc1.c1ccccc1 | null | c1cncnc1.C1C[C@@H]2C[C@@H](CO2)O1 | Other | [OH-].[OH-].[Pd+2].C(C)O | null | 26 | Cc1cn([C@@H]2O[C@H]3[C@@H](OCc4ccccc4)[C@@H]2OC[C@H]3OCc2ccccc2)c(=O)[nH]c1=O>[OH-].[OH-].[Pd+2].C(C)O>Cc1cn([C@@H]2O[C@H]3[C@@H](O)[C@@H]2OC[C@H]3O)c(=O)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0f8d0671097c4c1fb7b5e5e1778ceb8b | C#CCN1CCCCC1.Cc1ccccc1I>>Cc1ccccc1C#CCN1CCCCC1 | IC1=C(C=CC=C1)C.C(C#C)N1CCCCC1>>C1(=C(C=CC=C1)C#CCN1CCCCC1)C | [CH:8]#[C:9][CH2:10][N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1.I[c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8]#[C:9][CH2:10][N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1 | C#CCN1CCCCC1.Cc1ccccc1I | Cc1ccccc1C#CCN1CCCCC1 | null | Cl[Pd-2](P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)Cl.[Cu]I | C(C)NCC | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1ccccc1)CN1CCCCC1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[C:7]-[C:8]#[CH;D1;+0:9]>>[C:7]-[C:8]#[C;H0;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6] | 62.3 | [{"value": 62.3, "product": "C1(=C(C=CC=C1)C#CCN1CCCCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-iodotoluene (6.54 g), N-(2-propynyl)piperidine (3.69 g), dichlorobis(triphenylphosphino)palladium(II) (0.05 g) and copper(I) iodide (0.1 g) in dry diethylamine (50 ml) was heated under reflux for 5 hours. The solvent was removed under reduced pressure and the residue was taken up in diethyl ether and was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]CC1 | HI | Cl[Pd-2](P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)Cl.[Cu]I.C(C)NCC | null | null | C#CCN1CCCCC1.Cc1ccccc1I>Cl[Pd-2](P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)(P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)Cl.[Cu]I.C(C)NCC>Cc1ccccc1C#CCN1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6115213f3bde4e5a9ca0fe44acf19734 | C#CCCl.C1CCNCC1>>C#CCN1CCCCC1 | C(C#C)Cl.N1CCCCC1>>C(C#C)N1CCCCC1 | Cl[CH2:3][C:2]#[CH:1].[NH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1>>[CH:1]#[C:2][CH2:3][N:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1 | C#CCCl.C1CCNCC1 | C#CCN1CCCCC1 | null | null | CO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1CCNCC1 | Cl-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3])-[C:7]-[C:8] | null | [] | null | null | null | null | With stirring, a solution of 2-propynyl chloride (40.31 g) in dry methanol (50 ml) was added dropwise to a solution of piperidine (92.14 g) in dry methanol (100 ml). The mixture was stirred at 25° C. for 3 hours and then filtered. The filtrate was concentrated under reduced pressure and the residue was distilled (boili... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HCl | CO | null | null | C#CCCl.C1CCNCC1>CO>C#CCN1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-407eb598551c4c3b88f8f45387ed5837 | C#CCN1CCC(C)CC1.Fc1cccc(I)c1>>CC1CCN(CC#Cc2cccc(F)c2)CC1 | FC=1C=C(C=CC1)I.CC1CCN(CC1)CC#C>>FC=1C=C(C=CC1)C#CCN1CCC(CC1)C | [CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][C:7]#[CH:8])[CH2:16][CH2:17]1.I[c:9]1[cH:10][cH:11][cH:12][c:13]([F:14])[cH:15]1>>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([CH2:6][C:7]#[C:8][c:9]2[cH:10][cH:11][cH:12][c:13]([F:14])[cH:15]2)[CH2:16][CH2:17]1 | C#CCN1CCC(C)CC1.Fc1cccc(I)c1 | CC1CCN(CC#Cc2cccc(F)c2)CC1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].[Cu]I.C=1(C(=CC=CC1)C(=O)P(C(=O)C=1C(=CC=CC1)C)C(=O)C=1C(=CC=CC1)C)C | C(C)NCC | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1ccccc1)CN1CCCCC1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]#[CH;D1;+0:8]>>[C:6]-[C:7]#[C;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 56.2 | [{"value": 56.2, "product": "FC=1C=C(C=CC1)C#CCN1CCC(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-fluoroiodobenzene (8.88 g), 4-methyl-1-(2-propynyl)piperidine (6.80 g), palladium acetate (0.045 g), tri-o-toloylphosphine (0.24 g) and copper(I) iodide (0.1 g) in dry diethylamine (50 ml) was heated under reflux for 5 hours. The solvent was removed under reduced pressure and the residue was taken up in ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | C1CC[NH]CC1.c1ccccc1 | HI | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].[Cu]I.C=1(C(=CC=CC1)C(=O)P(C(=O)C=1C(=CC=CC1)C)C(=O)C=1C(=CC=CC1)C)C.C(C)NCC | null | null | C#CCN1CCC(C)CC1.Fc1cccc(I)c1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].[Cu]I.C=1(C(=CC=CC1)C(=O)P(C(=O)C=1C(=CC=CC1)C)C(=O)C=1C(=CC=CC1)C)C.C(C)NCC>CC1CCN(CC#Cc2cccc(F)c2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3d1eef909b754b8da0b694cdccfec3a6 | C#CCBr.CC1CCNCC1>>C#CCN1CCC(C)CC1 | C(C#C)Br.CC1CCNCC1.C([O-])([O-])=O.[K+].[K+]>>CC1CCN(CC1)CC#C | Br[CH2:3][C:2]#[CH:1].[NH:4]1[CH2:5][CH2:6][CH:7]([CH3:8])[CH2:9][CH2:10]1>>[CH:1]#[C:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([CH3:8])[CH2:9][CH2:10]1 | C#CCBr.CC1CCNCC1 | C#CCN1CCC(C)CC1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1CCNCC1 | Br-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]#[C;D1;H1:3])-[C:7]-[C:8] | 92 | [{"value": 92.0, "product": "CC1CCN(CC1)CC#C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 6 | HOUR | At 0–5° C., propargyl bromide (12.01 g) was added dropwise with stirring to a suspension of 4-methylpiperidine (10.0 g) and potassium carbonate (13.96 g) in dry acetone (80 ml). The mixture was stirred at 50° C. for 6 hours and then filtered. The filtrate was concentrated under reduced pressure and the residue was take... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HBr | CC(=O)C | 50 | 6 | C#CCBr.CC1CCNCC1>CC(=O)C>C#CCN1CCC(C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a76fbde539d14fbe965fa11a289cc844 | C#Cc1ccccc1.C1CCNCC1.C=O>>C(#Cc1ccccc1)CN1CCCCC1 | Cl.C1(=CC=CC=C1)C#C.N1CCCCC1.C=O>>C1(=CC=CC=C1)C#CCN1CCCCC1 | [CH:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1.[NH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1.O=[CH2:9]>>[C:1](#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[CH2:9][N:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1 | C#Cc1ccccc1.C1CCNCC1.C=O | C(#Cc1ccccc1)CN1CCCCC1 | null | [Cu]Cl | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 1c251f14c75b80b0dd3c8a9f2ea21fcdf95b017bc463f94c2b4be04acef3803b | 7dc88503da2577b71123fe820b1c2cdad87aca8735340a4da3de40929f65c4dd | C(#Cc1ccccc1)CN1CCCCC1 | O=[CH2;D1;+0:1].[CH;D1;+0:2]#[C:3]-[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C;H0;D2;+0:2]#[C:3]-[c:4])-[C:8]-[C:9] | 65.3 | [{"value": 65.3, "product": "C1(=CC=CC=C1)C#CCN1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | null | null | With stirring, a solution of phenylacetylene (10.2 g) in dioxane (10 ml), a solution of piperidine (13.3 g) in dioxane (10 ml) and copper(I) chloride (0.1 g) were added successively to a suspension of paraformaldehyde (3.6 g) in dioxane (10 ml). The mixture was heated under reflux for 6 hours, allowed to cool to 25° C.... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine.Alkyne | Tertiary amine.Alkyne | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HO- | [Cu]Cl.O1CCOCC1 | 25 | null | C#Cc1ccccc1.C1CCNCC1.C=O>[Cu]Cl.O1CCOCC1>C(#Cc1ccccc1)CN1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-02f0b0daf7f34f13804f67028ba672a7 | C1CCNCC1.FC(F)(F)c1cc(C#CCBr)cc(C(F)(F)F)c1>>FC(F)(F)c1cc(C#CCN2CCCCC2)cc(C(F)(F)F)c1 | FC(C=1C=C(C=C(C1)C(F)(F)F)C#CCBr)(F)F.N1CCCCC1.C([O-])([O-])=O.[K+].[K+]>>FC(C=1C=C(C=C(C1)C(F)(F)F)C#CCN1CCCCC1)(F)F | [NH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1.Br[CH2:10][C:9]#[C:8][c:7]1[cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:23][c:18]([C:19]([F:20])([F:21])[F:22])[cH:17]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][c:7]([C:8]#[C:9][CH2:10][N:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[cH:17][c:18]([C:19]([F:20])([F:21])[F:22])... | C1CCNCC1.FC(F)(F)c1cc(C#CCBr)cc(C(F)(F)F)c1 | FC(F)(F)c1cc(C#CCN2CCCCC2)cc(C(F)(F)F)c1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C(#Cc1ccccc1)CN1CCCCC1 | Br-[CH2;D2;+0:1]-[C:2]#[C:3]-[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C:2]#[C:3]-[c:4])-[C:8]-[C:9] | null | [] | null | null | 18 | HOUR | A mixture of 1-(3,5-bistrifluoromethylphenyl)-3-bromoprop-1-yne (2.53 g), piperidine (5 ml) and anhydrous potassium carbonate (5 g) in dry acetone (50 ml) was heated at reflux with stirring for 18 h. Removal of the solvent under reduced pressure and distillation of the residue under reduced pressure gave 2.26 g of an o... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HBr | CC(=O)C | null | 18 | C1CCNCC1.FC(F)(F)c1cc(C#CCBr)cc(C(F)(F)F)c1>CC(=O)C>FC(F)(F)c1cc(C#CCN2CCCCC2)cc(C(F)(F)F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed06c24c01b04411accf6dff0f2cccde | FC(F)(F)c1cc(C#CCN2CCCCC2)cc(C(F)(F)F)c1>>FC(F)(F)c1cc(C#CCN2CCCCC2)cc(C(F)(F)F)c1 | Cl.FC(C=1C=C(C=C(C1)C(F)(F)F)C#CCN1CCCCC1)(F)F>>Cl.FC(C=1C=C(C=C(C1)C(F)(F)F)C#CCN1CCCCC1)(F)F | [F:2][C:3]([F:4])([F:5])[c:6]1[cH:7][c:8]([C:9]#[C:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24]1>>[F:2][C:3]([F:4])([F:5])[c:6]1[cH:7][c:8]([C:9]#[C:10][CH2:11][N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[c... | FC(F)(F)c1cc(C#CCN2CCCCC2)cc(C(F)(F)F)c1 | FC(F)(F)c1cc(C#CCN2CCCCC2)cc(C(F)(F)F)c1 | null | null | C(C)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C(#Cc1ccccc1)CN1CCCCC1 | null | null | [] | null | null | null | null | An excess of dry HCl gas was passed through a solution of 1-(3,5-bistrifluoromethylphenyl)-3-piperidinoprop-1-yne (2.26 g) in dry diethyl ether (200 ml). Filtration, washing (diethyl ether) and drying of the resulting white precipitate gave 2.16 g of a fine white powder of melting point 214.5° C.
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.C1CC[NH]CC1 | null | C(C)OCC | null | null | FC(F)(F)c1cc(C#CCN2CCCCC2)cc(C(F)(F)F)c1>C(C)OCC>FC(F)(F)c1cc(C#CCN2CCCCC2)cc(C(F)(F)F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0a730dd69aee4455b345209e15cac609 | C1CCNCC1.O=[N+]([O-])c1ccc2nc(Cl)ccc2c1>>O=[N+]([O-])c1ccc2nc(N3CCCCC3)ccc2c1 | ClC1=NC2=CC=C(C=C2C=C1)[N+](=O)[O-].N1CCCCC1>>[N+](=O)([O-])C=1C=C2C=CC(=NC2=CC1)N1CCCCC1 | [NH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1.Cl[c:9]1[n:8][c:7]2[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:19][c:18]2[cH:17][cH:16]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([N:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)[cH:16][cH:17][c:18]2[cH:19]1 | C1CCNCC1.O=[N+]([O-])c1ccc2nc(Cl)ccc2c1 | O=[N+]([O-])c1ccc2nc(N3CCCCC3)ccc2c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 6ca896bdf5cf17e98a9402041cc62e117ebb3e6ff582ec413fbc5219ab9874c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2nc(N3CCCCC3)ccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5])-[C:9]-[C:10] | null | [] | null | null | null | null | The product (208 mg, 1.0 mmol) from Step B and piperidine (0.5 mL, 5 mmol) were mixed in absolute ethanol (3 mL) and then heated at reflux for 4 h. The reaction mixture was cooled to r.t., and the solvent removed under vacuum. The solids were taken up in EtOAc (125 mL). The mixture was transferred to a separatory funne... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNCC1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.C1CC[NH]CC1 | c1ccc2ncccc2c1.C1CC[NH]CC1 | HCl | C(C)O | null | null | C1CCNCC1.O=[N+]([O-])c1ccc2nc(Cl)ccc2c1>C(C)O>O=[N+]([O-])c1ccc2nc(N3CCCCC3)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7a8c29af5c6d4ed5850e6a506f148c64 | O=[N+]([O-])c1ccc2nc(N3CCCCC3)ccc2c1>>Nc1ccc2nc(N3CCCCC3)ccc2c1 | [N+](=O)([O-])C=1C=C2C=CC(=NC2=CC1)N1CCCCC1>>N1(CCCCC1)C1=NC2=CC=C(C=C2C=C1)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]3)[cH:14][cH:15][c:16]2[cH:17]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]3)[cH:14][cH:15][c:16]2[cH:17]1 | O=[N+]([O-])c1ccc2nc(N3CCCCC3)ccc2c1 | Nc1ccc2nc(N3CCCCC3)ccc2c1 | null | [OH-].[OH-].[Pd+2] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2nc(N3CCCCC3)ccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | The product (204 mg, 0.8 mmol) of Step C and palladium hydroxide on carbon (100 mg) was suspended in methanol. The resulting mixture was degassed then stirred under hydrogen atmosphere (balloon) until all the yellow solids had dissolved. The reaction mixture was filtered through filter aid and the solvent removed under... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1.C1CC[NH]CC1 | Other | [OH-].[OH-].[Pd+2].CO | null | null | O=[N+]([O-])c1ccc2nc(N3CCCCC3)ccc2c1>[OH-].[OH-].[Pd+2].CO>Nc1ccc2nc(N3CCCCC3)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-98ba0a4789094cd8bd645b484b6e0ba8 | O=C(Cl)C(=O)Cl.O=C(O)/C=C/c1ccc(Cl)cc1>>O=C(Cl)/C=C/c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)/C=C/C(=O)O.C(C(=O)Cl)(=O)Cl.CN(C=O)C>>ClC1=CC=C(C=C1)/C=C/C(=O)Cl | O=C(Cl)C(=O)[Cl:3].O[C:2](=[O:1])/[CH:4]=[CH:5]/[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1>>[O:1]=[C:2]([Cl:3])/[CH:4]=[CH:5]/[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1 | O=C(Cl)C(=O)Cl.O=C(O)/C=C/c1ccc(Cl)cc1 | O=C(Cl)/C=C/c1ccc(Cl)cc1 | null | null | C(Cl)Cl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccccc1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])/[C:4]=[C:5]/[c:6](:[c:7]):[c:8]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])/[C:4]=[C:5]/[c:6](:[c:7]):[c:8] | null | [] | null | null | 6 | HOUR | To a solution of (2E)-3-(4-chlorophenyl)prop-2-enoic acid (2.0 g, 11 mmol) in 50 mL methylene chloride was added oxalyl chloride (1.05 mL, 12.1 mmol) and N,N-dimethylformamide (0.05 mL, 0.6 mmol). The resulting mixture was stirred at r.t. for 6 h. The solvent was removed under vacuum. The resulting solid was diluted wi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | C(Cl)Cl | null | 6 | O=C(Cl)C(=O)Cl.O=C(O)/C=C/c1ccc(Cl)cc1>C(Cl)Cl>O=C(Cl)/C=C/c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7ea16d5540f64108a374fefb1059f324 | Nc1ccc2nc(N3CCCCC3)ccc2c1.O=C(Cl)/C=C/c1ccc(Cl)cc1>>Cl.O=C(/C=C/c1ccc(Cl)cc1)Nc1ccc2nc(N3CCCCC3)ccc2c1 | N1=C(C=CC2=CC(=CC=C12)N)N.N1(CCCCC1)C1=NC2=CC=C(C=C2C=C1)N.ClC1=CC=C(C=C1)/C=C/C(=O)Cl>>Cl.ClC1=CC=C(C=C1)/C=C/C(=O)NC=1C=C2C=CC(=NC2=CC1)N1CCCCC1 | [NH2:13][c:14]1[cH:15][cH:16][c:17]2[n:18][c:19]([N:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[cH:26][cH:27][c:28]2[cH:29]1.[Cl:1][C:3](=[O:2])/[CH:4]=[CH:5]/[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1>>[ClH:1].[O:2]=[C:3](/[CH:4]=[CH:5]/[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]1)[NH:13][c:14]1[cH:15][cH:1... | Nc1ccc2nc(N3CCCCC3)ccc2c1.O=C(Cl)/C=C/c1ccc(Cl)cc1 | Cl.O=C(/C=C/c1ccc(Cl)cc1)Nc1ccc2nc(N3CCCCC3)ccc2c1 | null | null | CCOCC.CC(=O)O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(/C=C/c1ccccc1)Nc1ccc2nc(N3CCCCC3)ccc2c1 | [Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])/[C:4]=[C:5]/[c:6](:[c:7]):[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[ClH;D0;+0:1].[O;D1;H0:3]=[C;H0;D3;+0:2](/[C:4]=[C:5]/[c:6](:[c:7]):[c:8])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12] | null | [] | null | null | 3 | HOUR | To a solution of the product of Step D (91 mg, 0.4 mmol) in 2 mL HOAc was added the product of Step E (64 mg, 0.32 mmol). The resulting mixture was stirred at r.t. for 3 h then diluted with 3 mL ether. The resulting mixture was filtered and the resulting solids were washed with ether. The solids were dried under vacuum... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccc2ncccc2c1.C1CC[NH]CC1 | null | CCOCC.CC(=O)O | null | 3 | Nc1ccc2nc(N3CCCCC3)ccc2c1.O=C(Cl)/C=C/c1ccc(Cl)cc1>CCOCC.CC(=O)O>Cl.O=C(/C=C/c1ccc(Cl)cc1)Nc1ccc2nc(N3CCCCC3)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a3165b7ee2534a77974b2be0553c8d96 | C1CC2CCC1CN2.O=[N+]([O-])c1ccc2nc(Cl)ccc2c1>>O=[N+]([O-])c1ccc2nc(N3CC4CCC3CC4)ccc2c1 | ClC1=NC2=CC=C(C=C2C=C1)[N+](=O)[O-].C1(=CC=C(C=C1)S(=O)(=O)O)C.C12NCC(CC1)CC2.C([O-])(O)=O.[Na+]>>C12N(CC(CC1)CC2)C2=NC1=CC=C(C=C1C=C2)[N+](=O)[O-] | [NH:10]1[CH2:11][CH:12]2[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]2.Cl[c:9]1[n:8][c:7]2[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:21][c:20]2[cH:19][cH:18]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([N:10]3[CH2:11][CH:12]4[CH2:13][CH2:14][CH:15]3[CH2:16][CH2:17]4)[cH:18][cH:19][c:20]2[cH:21]1 | C1CC2CCC1CN2.O=[N+]([O-])c1ccc2nc(Cl)ccc2c1 | O=[N+]([O-])c1ccc2nc(N3CC4CCC3CC4)ccc2c1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 5b793ed73287579d6768ac1b84becbeb1432f1e0031d905191aa89becd4e0492 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2nc(N3CC4CCC3CC4)ccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9](-[C:10])-[C:11]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5])-[C:9](-[C:10])-[C:11] | null | [] | null | null | null | null | A mixture of 2-chloro-6-nitroquinoline (5.0 g, 24 mmol, Example 1, Step B), 2-azabicyclo[2.2.2]octane p-toluenesulfonic acid salt (10.2 g, 36 mmol) and sodium bicarbonate (5.1 g, 60 mmol) were mixed in absolute ethanol (100 mL) and then heated at reflux for 24 h. The reaction mixture was cooled to r.t., and the solvent... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncccc2c1.C1CC2CCC1CN2 | c1ccc2ncccc2c1.C1CC2CCC1C[NH]2 | c1ccc2ncccc2c1.C1CC2CCC1C[NH]2 | HCl | C(C)O | null | null | C1CC2CCC1CN2.O=[N+]([O-])c1ccc2nc(Cl)ccc2c1>C(C)O>O=[N+]([O-])c1ccc2nc(N3CC4CCC3CC4)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-941df1acbb1249ef9c18b030f6937c2a | O=[N+]([O-])c1ccc2nc(N3CC4CCC3CC4)ccc2c1>>Nc1ccc2nc(N3CC4CCC3CC4)ccc2c1 | C12N(CC(CC1)CC2)C2=NC1=CC=C(C=C1C=C2)[N+](=O)[O-]>>C12N(CC(CC1)CC2)C2=NC1=CC=C(C=C1C=C2)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH:10]4[CH2:11][CH2:12][CH:13]3[CH2:14][CH2:15]4)[cH:16][cH:17][c:18]2[cH:19]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH:10]4[CH2:11][CH2:12][CH:13]3[CH2:14][CH2:15]4)[cH:16][cH:17][c:18]2[cH:19]1 | O=[N+]([O-])c1ccc2nc(N3CC4CCC3CC4)ccc2c1 | Nc1ccc2nc(N3CC4CCC3CC4)ccc2c1 | null | [OH-].[OH-].[Pd+2] | CO.C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2nc(N3CC4CCC3CC4)ccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 6 | HOUR | The product of Step A and palladium hydroxide on carbon (1.3 g, 20% by wt) was suspended in methanol (100 mL) and ethyl acetate (100 mL). The resulting mixture was degassed then stirred under hydrogen atmosphere (balloon) for 6 h. The reaction mixture was filtered through filter aid and the solvent removed under vacuum... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1.C1CC2CCC1C[NH]2 | Other | [OH-].[OH-].[Pd+2].CO.C(C)(=O)OCC | null | 6 | O=[N+]([O-])c1ccc2nc(N3CC4CCC3CC4)ccc2c1>[OH-].[OH-].[Pd+2].CO.C(C)(=O)OCC>Nc1ccc2nc(N3CC4CCC3CC4)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-88fe29ea69b54e5088b5bb28e789c315 | CC(C)(C)OC(=O)C=Cc1ccc(C(F)(F)F)nc1>>CC(C)(C)OC(=O)CCc1ccc(C(F)(F)F)nc1 | FC(C1=CC=C(C=N1)C=CC(=O)OC(C)(C)C)(F)F>>FC(C1=CC=C(C=N1)CCC(=O)OC(C)(C)C)(F)F | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH:8]=[CH:9][c:10]1[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[n:18][cH:19]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[n:18][cH:19]1 | CC(C)(C)OC(=O)C=Cc1ccc(C(F)(F)F)nc1 | CC(C)(C)OC(=O)CCc1ccc(C(F)(F)F)nc1 | null | [Pd] | CO | Reduction | Hydrogenation (double to single) | c04c38f95d7b746e5bdb99c368a7a33956c97b95b54c7ad89be2a85526386ec9 | 9a50abf8d2e4cd9195d7a0cadbe97483a261a81cf70b653cfddd5ecf76d383a6 | c1ccncc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D2;+0:8]=[CH;D2;+0:9]-[c:10](:[c:11]):[c:12]:[#7;a:13]:[c:14]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[c:10](:[c:11]):[c:12]:[#7;a:13]:[c:14] | null | [] | null | null | null | null | The product of Step C (2.2 g, 8.1 mmol) in 40 mL methanol and 5% palladium on carbon (0.25 g) was stirred under hydrogen atmosphere (balloon) for 1 h. The reaction mixture was filtered through filter aid and the solvent removed under vacuum to afford the product as a solid, MS: m/z 276 (MH+).
Conditions: See reaction.n... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccncc1 | null | [Pd].CO | null | null | CC(C)(C)OC(=O)C=Cc1ccc(C(F)(F)F)nc1>[Pd].CO>CC(C)(C)OC(=O)CCc1ccc(C(F)(F)F)nc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c1bf5a8f124408fb10931da146f70b7 | Nc1ccc2nc(N3CC4CCC3CC4)ccc2c1.O=C(O)CCc1ccc(C(F)(F)F)nc1>>O=C(CCc1ccc(C(F)(F)F)nc1)Nc1ccc2nc(N3CC4CCC3CC4)ccc2c1 | C12N(CC(CC1)CC2)C2=NC1=CC=C(C=C1C=C2)N.FC(C1=CC=C(C=N1)CCC(=O)O)(F)F.C(C)N(CC)CC.Cl.CN(CCCN=C=NCC)C>>C12N(CC(CC1)CC2)C2=NC1=CC=C(C=C1C=C2)NC(CCC=2C=NC(=CC2)C(F)(F)F)=O | [NH2:15][c:16]1[cH:17][cH:18][c:19]2[n:20][c:21]([N:22]3[CH2:23][CH:24]4[CH2:25][CH2:26][CH:27]3[CH2:28][CH2:29]4)[cH:30][cH:31][c:32]2[cH:33]1.O[C:2](=[O:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[n:13][cH:14]1>>[O:1]=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[n... | Nc1ccc2nc(N3CC4CCC3CC4)ccc2c1.O=C(O)CCc1ccc(C(F)(F)F)nc1 | O=C(CCc1ccc(C(F)(F)F)nc1)Nc1ccc2nc(N3CC4CCC3CC4)ccc2c1 | null | CN(C1=CC=NC=C1)C | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCc1cccnc1)Nc1ccc2nc(N3CC4CCC3CC4)ccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 3 | DAY | To a solution of the product of Step B (307 mg, 1.2 mmol), the product of Step E (404 mg, 1.2 mmol) and triethylamine (0.17 mL, 1.2 mmol) in 10 mL methylene chloride was added 4-dimethylaminopyridine (222 mg, 1.8 mmol) followed by 1-(3-dimethylaminopropyl)3-ethylcarbodiimide HCl (349 mg, 1.82 mmol). The resulting mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccc2ncccc2c1.C1CC2CCC1C[NH]2 | HO- | CN(C1=CC=NC=C1)C.C(Cl)Cl | null | 72 | Nc1ccc2nc(N3CC4CCC3CC4)ccc2c1.O=C(O)CCc1ccc(C(F)(F)F)nc1>CN(C1=CC=NC=C1)C.C(Cl)Cl>O=C(CCc1ccc(C(F)(F)F)nc1)Nc1ccc2nc(N3CC4CCC3CC4)ccc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0e4d511f1a244853a580e3f8bc3bfe7d | CSc1ccc(N=C=O)cc1.Nc1ccc2nc(N3CC4CCC3CC4)ccc2c1>>CSc1ccc(NC(=O)Nc2ccc3nc(N4CC5CCC4CC5)ccc3c2)cc1 | C12N(CC(CC1)CC2)C2=NC1=CC=C(C=C1C=C2)N.C(C)N(CC)CC.CSC1=CC=C(C=C1)N=C=O>>C12N(CC(CC1)CC2)C2=NC1=CC=C(C=C1C=C2)NC(=O)NC2=CC=C(C=C2)SC | [CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([N:7]=[C:8]=[O:9])[cH:29][cH:30]1.[NH2:10][c:11]1[cH:12][cH:13][c:14]2[n:15][c:16]([N:17]3[CH2:18][CH:19]4[CH2:20][CH2:21][CH:22]3[CH2:23][CH2:24]4)[cH:25][cH:26][c:27]2[cH:28]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[NH:10][c:11]2[cH:12][cH:13][c:14]3[n:15][c:16]([N... | CSc1ccc(N=C=O)cc1.Nc1ccc2nc(N3CC4CCC3CC4)ccc2c1 | CSc1ccc(NC(=O)Nc2ccc3nc(N4CC5CCC4CC5)ccc3c2)cc1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(Nc1ccccc1)Nc1ccc2nc(N3CC4CCC3CC4)ccc2c1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | 2 | HOUR | To a solution of 2-(2-azabicyclo[2.2.2]oct-2-yl)quinolin-6-amine (21 mg, 0.08 mmol, Example 119, Step B), triethylamine (0.013 mL, 0.09 mmol) in 1 mL methylene chloride was added 4-(methylthio)phenylisocyanate (15 mg, 0.09 mmol). The resulting mixture was stirred at r.t. for 2 h. The solvent was removed under vacuum an... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccc2ncccc2c1.C1CC2CCC1C[NH]2 | null | C(Cl)Cl | null | 2 | CSc1ccc(N=C=O)cc1.Nc1ccc2nc(N3CC4CCC3CC4)ccc2c1>C(Cl)Cl>CSc1ccc(NC(=O)Nc2ccc3nc(N4CC5CCC4CC5)ccc3c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d813e8fedc748868d00c8e9808dda4f | CCC(=O)Cl.Nc1ccc([N+](=O)[O-])cc1>>Cc1cc2cc([N+](=O)[O-])ccc2nc1Cl | C(C)N(CC)CC.P(=O)(Cl)(Cl)Cl.[N+](=O)([O-])C1=CC=C(N)C=C1.C(CC)(=O)Cl>>ClC1=NC2=CC=C(C=C2C=C1C)[N+](=O)[O-] | O=[C:14]([CH2:2][CH3:1])[Cl:15].[cH:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12]1[NH2:13]>>[CH3:1][c:2]1[cH:3][c:4]2[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][cH:11][c:12]2[n:13][c:14]1[Cl:15] | CCC(=O)Cl.Nc1ccc([N+](=O)[O-])cc1 | Cc1cc2cc([N+](=O)[O-])ccc2nc1Cl | null | null | C(Cl)(Cl)Cl.CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 81775abe7116e822e4b834c3d3d518d0edcb09b0ec8e35569a029e49c7a872c9 | bad03858dcf650cf645ccdaf2aaa3c22b96723f842a7ac6ef0b5bd082f0dbfb0 | c1ccc2ncccc2c1 | O=[C;H0;D3;+0:1](-[Cl;D1;H0:2])-[CH2;D2;+0:3]-[C;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[C;D1;H3:4]-[c;H0;D3;+0:3]1:[c:11]:[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:6](:[c:7]):[n;H0;D2;+0:5]:[c;H0;D3;+0:1]:1-[Cl;D1;H0:2] | null | [] | null | null | 2 | HOUR | To a solution of 4-nitroaniline (10 g, 72 mmol) in chloroform at 0° was added propionyl chloride (7 mL, 80 mol) followed by triethylamine (11.1 mL). The resulting solution was stirred for 2 h at r.t. at which time the reaction mixture was washed with aq. 2N HCl. The organic layer was dried filtered and the solvent remo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Aromatic halide | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | null | C(Cl)(Cl)Cl.CN(C=O)C | null | 2 | CCC(=O)Cl.Nc1ccc([N+](=O)[O-])cc1>C(Cl)(Cl)Cl.CN(C=O)C>Cc1cc2cc([N+](=O)[O-])ccc2nc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6fe6e3cc88c24bf59c2bd7d84afa2c25 | CCN.Cc1cc2cc([N+](=O)[O-])ccc2nc1Cl>>CCNc1nc2ccc([N+](=O)[O-])cc2cc1C | ClC1=NC2=CC=C(C=C2C=C1C)[N+](=O)[O-].C(C)N.CO>>C(C)NC1=NC2=CC=C(C=C2C=C1C)[N+](=O)[O-] | [CH3:1][CH2:2][NH2:3].Cl[c:4]1[n:5][c:6]2[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]2[cH:15][c:16]1[CH3:17]>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][c:6]2[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]2[cH:15][c:16]1[CH3:17] | CCN.Cc1cc2cc([N+](=O)[O-])ccc2nc1Cl | CCNc1nc2ccc([N+](=O)[O-])cc2cc1C | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6].[C;D1;H3:7]-[C:8]-[NH2;D1;+0:9]>>[C;D1;H3:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C;D1;H3:7]):[#7;a:2]:[c:3] | null | [] | null | null | null | null | The product (1 g, 4.5 mmol) from Step A and a solution of 2N ethylamine in methanol (5 mL, 25 mmol) were used to prepare the product according to the procedure of Example 1, Step C.
Conditions: See reaction.notes.procedure_details.
Workup: to prepare the product | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | null | null | null | CCN.Cc1cc2cc([N+](=O)[O-])ccc2nc1Cl>>CCNc1nc2ccc([N+](=O)[O-])cc2cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bc1ae466ad6d421a8c6e6bc08d31abd8 | CCNc1nc2ccc([N+](=O)[O-])cc2cc1C>>CCNc1nc2ccc(N)cc2cc1C | C(C)NC1=NC2=CC=C(C=C2C=C1C)[N+](=O)[O-]>>C(C)NC1=NC2=CC=C(C=C2C=C1C)N | O=[N+:10]([O-])[c:9]1[cH:8][cH:7][c:6]2[n:5][c:4]([NH:3][CH2:2][CH3:1])[c:14]([CH3:15])[cH:13][c:12]2[cH:11]1>>[CH3:1][CH2:2][NH:3][c:4]1[n:5][c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:11][c:12]2[cH:13][c:14]1[CH3:15] | CCNc1nc2ccc([N+](=O)[O-])cc2cc1C | CCNc1nc2ccc(N)cc2cc1C | null | [Pt]=O | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ncccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | The product (0.8 g) of Step B and platinum oxide on carbon (˜80 mg) was suspended in methanol. The resulting mixture was hydrogenated at 50 PSI for 1 h. The reaction mixture was filtered through filter aid and the solvent removed under vacuum to afford the product, which was used without further purification.
Condition... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1 | Other | [Pt]=O.CO | null | 1 | CCNc1nc2ccc([N+](=O)[O-])cc2cc1C>[Pt]=O.CO>CCNc1nc2ccc(N)cc2cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cfe0504a405f4962a2ce31424bdb5876 | Cc1cc(=O)[nH]c2ccccc12.O=P(Cl)(Cl)Cl.O=[N+]([O-])O>>Cc1cc(Cl)nc2ccc([N+](=O)[O-])cc12 | P(=O)(Cl)(Cl)Cl.CC1=CC(NC2=CC=CC=C12)=O.[N+](=O)(O)[O-]>>ClC1=NC2=CC=C(C=C2C(=C1)C)[N+](=O)[O-] | O=[c:4]1[cH:3][c:2]([CH3:1])[c:15]2[c:7]([nH:6]1)[cH:8][cH:9][cH:10][cH:14]2.O=P(Cl)(Cl)[Cl:5].O[N+:11](=[O:12])[O-:13]>>[CH3:1][c:2]1[cH:3][c:4]([Cl:5])[n:6][c:7]2[cH:8][cH:9][c:10]([N+:11](=[O:12])[O-:13])[cH:14][c:15]12 | Cc1cc(=O)[nH]c2ccccc12.O=P(Cl)(Cl)Cl.O=[N+]([O-])O | Cc1cc(Cl)nc2ccc([N+](=O)[O-])cc12 | null | null | S(O)(O)(=O)=O | Heteroatom Alkylation and Arylation | OtherReaction | f20387215d8594a87bef9da5b665c39f4e201faf5351d4443de4fbd02269cb14 | f6537f63bb6d84b288220699d1d6bf5b093efadadfedfa20e42b65bede0c93a6 | c1ccc2ncccc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[N+;H0;D3:2](-[O;-;D1;H0:3])=[O;D1;H0:4].O=[c;H0;D3;+0:5]1:[c:6]:[c:7]:[c:8]2:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]:[c:13]:2:[nH;D2;+0:14]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:5]1:[c:6]:[c:7]:[c:8]2:[c:9]:[c;H0;D3;+0:10](-[N+;H0;D3:2](-[O;-;D1;H0:3])=[O;D1;H0:4]):[c:11]:[c:12]:[c:13]:2:[n;H0;D2;+0... | null | [] | null | null | null | null | To a solution of 4-methylquinolin-2(1H)-one (11 g, 69 mmol) in concentrated sulfuric acid (100 mL) was added fuming nitric acid (2.7 mL, 80 mol). The temperature of the resulting solution rose to approximately 50°. The reaction mixture was heated at reflux for 1 h, cooled to r.t and carefully poured onto ice. The resul... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Aromatic halide.Nitro group | c1ccc2ccccc2n1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | S(O)(O)(=O)=O | null | null | Cc1cc(=O)[nH]c2ccccc12.O=P(Cl)(Cl)Cl.O=[N+]([O-])O>S(O)(O)(=O)=O>Cc1cc(Cl)nc2ccc([N+](=O)[O-])cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0cd5609f1a754f3db695d5fd5eadc6e8 | CNC.Cc1cc(Cl)nc2ccc([N+](=O)[O-])cc12>>Cc1cc(N(C)C)nc2ccc([N+](=O)[O-])cc12 | ClC1=NC2=CC=C(C=C2C(=C1)C)[N+](=O)[O-].CNC.CO>>CN(C1=NC2=CC=C(C=C2C(=C1)C)[N+](=O)[O-])C | [NH:5]([CH3:6])[CH3:7].Cl[c:4]1[cH:3][c:2]([CH3:1])[c:17]2[c:9]([n:8]1)[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16]2>>[CH3:1][c:2]1[cH:3][c:4]([N:5]([CH3:6])[CH3:7])[n:8][c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][c:17]12 | CNC.Cc1cc(Cl)nc2ccc([N+](=O)[O-])cc12 | Cc1cc(N(C)C)nc2ccc([N+](=O)[O-])cc12 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 58b519bcefc8b0884f30564d454d0bf8e19d1792705c71f74402c97f0a6633f3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[C;D1;H3:6]-[N;H0;D3;+0:7](-[C;D1;H3:8])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | The product was obtained from the product of Step A and a solution of 2N dimethylamine in methanol (5 mL, 25 mmol) according to the procedure of Example 1, Step C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | null | null | null | CNC.Cc1cc(Cl)nc2ccc([N+](=O)[O-])cc12>>Cc1cc(N(C)C)nc2ccc([N+](=O)[O-])cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-24b8824ab261437ea36ec379f8556894 | CI.Cc1cc(=O)[nH]c2ccccc12>>CCc1cc(=O)[nH]c2ccccc12 | CC1=CC(NC2=CC=CC=C12)=O.IC.C(CCC)[Li]>>C(C)C1=CC(NC2=CC=CC=C12)=O | I[CH3:1].[CH3:2][c:3]1[cH:4][c:5](=[O:6])[nH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12>>[CH3:1][CH2:2][c:3]1[cH:4][c:5](=[O:6])[nH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12 | CI.Cc1cc(=O)[nH]c2ccccc12 | CCc1cc(=O)[nH]c2ccccc12 | null | null | O1CCCC1 | C-C Coupling | Methylation with MeI_primary | 0e09d968095a587418cca2841b1e4f096e8103de8fbb60e833faf1fb3df36a41 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=c1ccc2ccccc2[nH]1 | I-[CH3;D1;+0:1].[CH3;D1;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | null | null | 0.5 | HOUR | To a suspension of 4-methylquinolin-2(1H)-one (5 g, 31 mmol) in anhydrous tetrahydrofuran (100 mL) under a nitrogen atmosphere cooled in an acetone/dry ice bath was added dropwise by syringe a 1.6N solution of n-butyl lithium in hexanes (49 mL, 78 mol). The resulting solution was warmed to r.t. for 2 h at which time io... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2ccccc2n1 | HI | O1CCCC1 | null | 0.5 | CI.Cc1cc(=O)[nH]c2ccccc12>O1CCCC1>CCc1cc(=O)[nH]c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1e08e61b53f5439a82e9262f353c1054 | CCc1cc(Cl)nc2ccc([N+](=O)[O-])cc12.CNC>>CCc1cc(N(C)C)nc2ccc([N+](=O)[O-])cc12 | ClC1=NC2=CC=C(C=C2C(=C1)CC)[N+](=O)[O-].CNC.CO>>C(C)C1=CC(=NC2=CC=C(C=C12)[N+](=O)[O-])N(C)C | Cl[c:5]1[cH:4][c:3]([CH2:2][CH3:1])[c:18]2[c:10]([n:9]1)[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]2.[NH:6]([CH3:7])[CH3:8]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([N:6]([CH3:7])[CH3:8])[n:9][c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][c:18]12 | CCc1cc(Cl)nc2ccc([N+](=O)[O-])cc12.CNC | CCc1cc(N(C)C)nc2ccc([N+](=O)[O-])cc12 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 58b519bcefc8b0884f30564d454d0bf8e19d1792705c71f74402c97f0a6633f3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C;D1;H3:8]>>[C;D1;H3:6]-[N;H0;D3;+0:7](-[C;D1;H3:8])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | The product was obtained from the product of Step B and a solution of 2N dimethyl-amine in methanol (5 mL, 25 mmol) according to the procedure of Example 1, Step C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | null | null | null | CCc1cc(Cl)nc2ccc([N+](=O)[O-])cc12.CNC>>CCc1cc(N(C)C)nc2ccc([N+](=O)[O-])cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce024ddd171d42738801fd911c4752bb | C/C(C(=O)[O-])=C(\C)C(=O)[O-].Nc1ccccc1I>>COC(=O)c1cc(=O)[nH]c2ccccc12 | IC1=C(N)C=CC=C1.C/C(=C(/C(=O)[O-])\C)/C(=O)[O-].C(C)N(CC)CC>>O=C1NC2=CC=CC=C2C(=C1)C(=O)OC | C/[C:6](=[C:5](\[CH3:1])[C:3]([O-:2])=[O:4])[C:7]([O-])=[O:8].I[c:15]1[c:10]([NH2:9])[cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](=[O:8])[nH:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]12 | C/C(C(=O)[O-])=C(\C)C(=O)[O-].Nc1ccccc1I | COC(=O)c1cc(=O)[nH]c2ccccc12 | null | C(C)(=O)[O-].C(C)(=O)[O-].[Pd+2] | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | 292f4863402eccd0a9f6dd16aafc3c44b8080c4e6519881a5c5ea4676bb35c24 | dae47bcfab7ed099e475eb403084a3a501504bafabddff3fe9757882fbed5be0 | O=c1ccc2ccccc2[nH]1 | C/[C;H0;D3;+0:1](=[C;H0;D3;+0:2](\[CH3;D1;+0:3])-[C:4](-[O-;H0;D1:5])=[O;D1;H0:6])-[C;H0;D3;+0:7](-[O-])=[O;D1;H0:8].I-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12](-[NH2;D1;+0:13]):[c:14]>>[CH3;D1;+0:3]-[O;H0;D2;+0:5]-[C:4](=[O;D1;H0:6])-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[c;H0;D3;+0:7](=[O;D1;H0:8]):[nH;D2;+0:13]:[c:12](:[c:14]):[... | null | [] | null | null | null | null | In a heavy-walled PYREX tube was placed 2-iodoaniline (2.84 g, 13 mmol), dimethylmaleate (2.44 g, 17 mmol), triethylamine (1.4 mL, 10 mmol), palladium diacetate (31 mg, 0.14 mmol) and 6 mL acetonitrile. The tube was flushed with nitrogen and sealed. The sealed tube was heated at 100° for 3.5 h then cooled to r.t. The t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Ester | c1ccccc1 | c1ccc2ccccc2n1 | c1ccc2ccccc2n1 | HI | C(C)(=O)[O-].C(C)(=O)[O-].[Pd+2].C(C)#N | null | null | C/C(C(=O)[O-])=C(\C)C(=O)[O-].Nc1ccccc1I>C(C)(=O)[O-].C(C)(=O)[O-].[Pd+2].C(C)#N>COC(=O)c1cc(=O)[nH]c2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d57d16896f9f4187ad5a58a2a543f654 | II.O=C1CCc2ccccc2N1>>O=C1CCc2cc(I)ccc2N1 | N1C(CCC2=CC=CC=C12)=O.II>>IC=1C=C2CCC(NC2=CC1)=O | I[I:8].[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:9][cH:10][c:11]2[NH:12]1>>[O:1]=[C:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([I:8])[cH:9][cH:10][c:11]2[NH:12]1 | II.O=C1CCc2ccccc2N1 | O=C1CCc2cc(I)ccc2N1 | null | S(=O)(=O)([O-])[O-].[Ag+].[Ag+] | C(C)O | Functional Group Interconversion | OtherReaction | 15c79cac3ef09004477b5129c0d571c16abbed1e80c5a42d5f5ded8c26dbac74 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C1CCc2ccccc2N1 | I-[I;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[I;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:3]:[c:2] | null | [] | null | null | 6 | HOUR | 3,4-Dihydroquinolin-2(1H)-one (7.5 g; 51 mmol) and silver (I) sulfate (17.5 g; 56.1 mmol) were suspended in ethanol (250 mL). A solution of iodine in ethanol (250 mL) was added slowly to the reaction over 1 hour. After 6 hours, the reaction was filtered through CELITE diatomaceous earth and washed copiously with methan... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2 | HI | S(=O)(=O)([O-])[O-].[Ag+].[Ag+].C(C)O | null | 6 | II.O=C1CCc2ccccc2N1>S(=O)(=O)([O-])[O-].[Ag+].[Ag+].C(C)O>O=C1CCc2cc(I)ccc2N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc386eeb65804bc3a3674cae524f7269 | O=C1CCc2cc(I)ccc2N1.[C-]#N>>N#Cc1ccc2c(c1)CCC(=O)N2 | IC=1C=C2CCC(NC2=CC1)=O.[C-]#N.[Na+]>>O=C1NC2=CC=C(C=C2CC1)C#N | I[c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][C:11](=[O:12])[NH:13]2.[N:1]#[C-:2]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][C:11](=[O:12])[NH:13]2 | O=C1CCc2cc(I)ccc2N1.[C-]#N | N#Cc1ccc2c(c1)CCC(=O)N2 | null | [Cu]I.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 | null | C-C Coupling | OtherReaction | 36fa9a6e6bf873a0f2099da43e55d765c21b9e5a7bf128c0f6fbc83033de8eb1 | 2549b026e730aedabd9d1c88337e10b7987bb7b86597cabf3fd7fef1a79c8a9a | O=C1CCc2ccccc2N1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C-;H0;D1:6]#[N;D1;H0:7]>>[N;D1;H0:7]#[C;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | 6-Iodo-3,4-dihydroquinolin-2(1H)-one (1.50 g; 5.50 mmol), sodium cyanide (0.54 g; 11.0 mmol), copper (I) iodide (0.105 g; 0.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.32 g; 0.3 mmol) were combined in a flask equipped with a reflux condenser. The flask was subjected to several evacuation-nitrogen purge cycl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2 | c1ccc2c(c1)CCCN2 | I- | [Cu]I.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 | null | null | O=C1CCc2cc(I)ccc2N1.[C-]#N>[Cu]I.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>N#Cc1ccc2c(c1)CCC(=O)N2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-410a6f1443c34331ba6735f7cc64c911 | CC(C)(C)C(=O)NC1CCN(c2ccc3cc(C#N)ccc3n2)C1.NO>>CC(C)(C)C(=O)NC1CCN(c2ccc3cc(C(=N)NO)ccc3n2)C1 | C(#N)C=1C=C2C=CC(=NC2=CC1)N1CC(CC1)NC(C(C)(C)C)=O.Cl.ON.C([O-])([O-])=O.[Na+].[Na+]>>ONC(C=1C=C2C=CC(=NC2=CC1)N1CC(CC1)NC(C(C)(C)C)=O)=N | [CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][CH:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]3[cH:16][c:17]([C:18]#[N:19])[cH:22][cH:23][c:24]3[n:25]2)[CH2:26]1.[NH2:20][OH:21]>>[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][CH:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]3[cH:16][c:17]([C:18](=[N... | CC(C)(C)C(=O)NC1CCN(c2ccc3cc(C#N)ccc3n2)C1.NO | CC(C)(C)C(=O)NC1CCN(c2ccc3cc(C(=N)NO)ccc3n2)C1 | null | null | ClCCl.O.C(C)O | Heteroatom Alkylation and Arylation | N-hydroxyimidamide from nitrile and hydroxylamine | 08a01a2d1cd9346f7b3dddbfcbf8124b349e5763794287a4a1b9ee287b4d6aa7 | 38c3b778e04536ea6155ce05fc7c4746354a32b3703099defb07490833e3a961 | c1ccc2nc(N3CCCC3)ccc2c1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[O;D1;H1:7]>>[NH;D1;+0:1]=[C;H0;D3;+0:2](-[NH;D2;+0:6]-[O;D1;H1:7])-[c:3](:[c:4]):[c:5] | null | [] | 90 | CELSIUS | null | null | A mixture of the product of Step D (60 mg; 0.1863 mmol), hydroxyl amine hydrochloride (3 eq.), sodium carbonate (4 eq.) in 1.5 mL water and 2.5 mL ethanol was heated to 90° C. for 6 h. The mixture was diluted with dichloromethane, washed twice with brine, dried over sodium sulfate, filtered through a fritted funnel and... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Secondary amine | null | null | C1CC[NH]C1.c1ccc2ncccc2c1 | null | ClCCl.O.C(C)O | 90 | null | CC(C)(C)C(=O)NC1CCN(c2ccc3cc(C#N)ccc3n2)C1.NO>ClCCl.O.C(C)O>CC(C)(C)C(=O)NC1CCN(c2ccc3cc(C(=N)NO)ccc3n2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5b2ee72421e84c96a53e63a90b2cd355 | CC(C(=O)O)c1ccc(C(F)(F)F)cc1.CC(C)(C)C(=O)NC1CCN(c2ccc3cc(C(=N)NO)ccc3n2)C1>>CC(C)(C)C(=O)NC1CCN(c2ccc3cc(-c4noc(CCc5ccc(C(F)(F)F)cc5)n4)ccc3n2)C1 | ONC(C=1C=C2C=CC(=NC2=CC1)N1CC(CC1)NC(C(C)(C)C)=O)=N.FC(C1=CC=C(C=C1)C(C(=O)O)C)(F)F.C(CCl)Cl>>CC(C(=O)NC1CN(CC1)C1=NC2=CC=C(C=C2C=C1)C1=NOC(=N1)CCC1=CC=C(C=C1)C(F)(F)F)(C)C | O=[C:21](O)[CH:23]([CH3:22])[c:24]1[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]1.[CH3:1][C:2]([CH3:3])([CH3:4])[C:5](=[O:6])[NH:7][CH:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]3[cH:16][c:17]([C:18]([NH:19][OH:20])=[NH:34])[cH:35][cH:36][c:37]3[n:38]2)[CH2:39]1>>[CH3:1][C:2]([CH3:3])([CH3:4... | CC(C(=O)O)c1ccc(C(F)(F)F)cc1.CC(C)(C)C(=O)NC1CCN(c2ccc3cc(C(=N)NO)ccc3n2)C1 | CC(C)(C)C(=O)NC1CCN(c2ccc3cc(-c4noc(CCc5ccc(C(F)(F)F)cc5)n4)ccc3n2)C1 | null | null | COCCOCCOC | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(CCc2nc(-c3ccc4nc(N5CCCC5)ccc4c3)no2)cc1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[CH3;D1;+0:3])-[c:4](:[c:5]):[c:6].[#7;a:7]:[c:8]1:[c:9]:[c:10]:[c;H0;D3;+0:11](-[C;H0;D3;+0:12](=[NH;D1;+0:13])-[NH;D2;+0:14]-[OH;D1;+0:15]):[c:16]:[c:17]:1>>[#7;a:7]:[c:8]1:[c:9]:[c:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:12]2:[n;H0;D2;+0:14]:[o;H0;D2;+0:15]:[c;H0;D3;+0:1](-[CH2;D2;+0:3]-[... | null | [] | 50 | CELSIUS | 18 | HOUR | To a mixture of the product of Step E, (66 mg) in anhydrous diglyme (2 mL) was added 4-trifluoromethylphenylpropionic acid (1.1 eq.) and EDC (2 eq.). The reaction mixture was heated to 50° C. overnight. After approximately 18 h, the mixture was heated at 110° C. for 2 hr. The mixture was cooled to r.t., quenched with w... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | C1CC[NH]C1.c1ccc2ncccc2c1.c1ncon1.c1ccccc1 | HO- | COCCOCCOC | 50 | 18 | CC(C(=O)O)c1ccc(C(F)(F)F)cc1.CC(C)(C)C(=O)NC1CCN(c2ccc3cc(C(=N)NO)ccc3n2)C1>COCCOCCOC>CC(C)(C)C(=O)NC1CCN(c2ccc3cc(-c4noc(CCc5ccc(C(F)(F)F)cc5)n4)ccc3n2)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1aa64b4167fe4b359e015b9b3ca05d8f | O=[N+]([O-])c1ccc(O)c(Br)c1.OCc1cccc(F)c1>>O=[N+]([O-])c1ccc(OCc2cccc(F)c2)c(Br)c1 | BrC1=C(C=CC(=C1)[N+](=O)[O-])O.FC=1C=C(CO)C=CC1.CC(C)OC(=O)/N=N/C(=O)OC(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrC1=C(C=CC(=C1)[N+](=O)[O-])OCC1=CC(=CC=C1)F | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[c:17]([Br:18])[cH:19]1.O[CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([F:15])[cH:16]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][c:14]([F:15])[cH:16]2)[c:17]([Br:18])[cH:19]1 | O=[N+]([O-])c1ccc(O)c(Br)c1.OCc1cccc(F)c1 | O=[N+]([O-])c1ccc(OCc2cccc(F)c2)c(Br)c1 | null | null | C1CCOC1.CCOC(=O)C.O | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(COc2ccccc2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 68 | [{"value": 68.0, "product": "BrC1=C(C=CC(=C1)[N+](=O)[O-])OCC1=CC(=CC=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.3, "product": "BrC1=C(C=CC(=C1)[N+](=O)[O-])OCC1=CC(=CC=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | 2-Bromo-4-nitrophenol (4.86 g, 0.0223 mol), triphenylphosphine (7.6 g, 0.0290 mol), 3-fluorobenzylalcohol (3.65 g, 0.0290 mol) were combined and dissolved in THF (89 mL). The reaction temperature was cooled to 0° C. and DIAD (4.50 g, 0.0290 mol) was added. The reaction was allowed to warm slowly to rt and stirred for 3... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HO- | C1CCOC1.CCOC(=O)C.O | 0 | 3 | O=[N+]([O-])c1ccc(O)c(Br)c1.OCc1cccc(F)c1>C1CCOC1.CCOC(=O)C.O>O=[N+]([O-])c1ccc(OCc2cccc(F)c2)c(Br)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-50a401181684469192a5170e3a2ba065 | CC(C)S(=O)(=O)CC#N>>CC(C)S(=O)(=O)CCN | C(C)(C)S(=O)(=O)CC#N.CSC.B.Cl>>C(C)(C)S(=O)(=O)CCN | [CH3:1][CH:2]([CH3:3])[S:4](=[O:5])(=[O:6])[CH2:7][C:8]#[N:9]>>[CH3:1][CH:2]([CH3:3])[S:4](=[O:5])(=[O:6])[CH2:7][CH2:8][NH2:9] | CC(C)S(=O)(=O)CC#N | CC(C)S(=O)(=O)CCN | null | null | C1CCOC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | null | [#16:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[#16:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | null | [] | null | null | 40 | MINUTE | Prepared according to Procedure K. 2-iso-Propylsulfonylacetonitrile (0.50 g, 3.39 mmol) was dissolved in THF and warmed to reflux under N2. Borane dimethylsulfide (2M, 1.7 mL, 3.39 mmol) was added dropwise and the reaction was stirred for an additional 40 minutes at reflux. After cooling the reaction to rt, HCl (2 M in... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | null | null | C1CCOC1 | null | 0.666667 | CC(C)S(=O)(=O)CC#N>C1CCOC1>CC(C)S(=O)(=O)CCN |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c203ffc909de4ce88f61035e85a6eb6c | Fc1cc2ncnc(Cl)c2cc1I.Nc1ccc(OCc2ccccc2)cc1>>Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I | Cl.ClC1=NC=NC2=CC(=C(C=C12)I)F.O1CCOCC1.Cl.C(C1=CC=CC=C1)OC1=CC=C(N)C=C1>>Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)I)F | Cl[c:9]1[n:8][cH:7][n:6][c:5]2[cH:4][c:3]([F:2])[c:27]([I:28])[cH:26][c:25]21.[NH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23][cH:24]1>>[F:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]4[cH:18][cH:19][cH:20][cH:21][c... | Fc1cc2ncnc(Cl)c2cc1I.Nc1ccc(OCc2ccccc2)cc1 | Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I | null | null | ClCCl | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4ccccc34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 79.1 | [{"value": 79.0, "product": "Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)I)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.1, "product": "Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)I)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | Prepared according to Procedure A from 4-chloro-6-iodo-7-fluoro-quinazoline hydrochloride (4.02 grams, 11.65 mmoles), anhydrous dioxane (70 ml), dichloromethane (20 ml), and 4-benzyloxyaniline hydrochloride (2.83 grams, 12 mmoles). The mixture was stirred and heated to 110° C. (oil bath temperature) for 16 hours, coole... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | HCl | ClCCl | 110 | null | Fc1cc2ncnc(Cl)c2cc1I.Nc1ccc(OCc2ccccc2)cc1>ClCCl>Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5899155eb2234a2e8997519924de4408 | Nc1ccc2c(=O)[nH]cnc2c1.[I-]>>O=c1[nH]cnc2cc(I)ccc12 | NC1=CC=C2C(NC=NC2=C1)=O.[I-].[K+].N(=O)[O-].[Na+]>>IC1=CC=C2C(NC=NC2=C1)=O | N[c:8]1[cH:7][c:6]2[n:5][cH:4][nH:3][c:2](=[O:1])[c:12]2[cH:11][cH:10]1.[I-:9]>>[O:1]=[c:2]1[nH:3][cH:4][n:5][c:6]2[cH:7][c:8]([I:9])[cH:10][cH:11][c:12]12 | Nc1ccc2c(=O)[nH]cnc2c1.[I-] | O=c1[nH]cnc2cc(I)ccc12 | null | null | O.Cl | Functional Group Interconversion | OtherReaction | 1fc01df8cde644f7b4f5f8066e7d4772323840e5c20b07166b24323c5f5d8071 | 9c224743a26d9e1c3135e4817dd611aec414d8ea156f02200a3aef865be78b01 | O=c1[nH]cnc2ccccc12 | N-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:1.[I-;H0;D0:11]>>[I;H0;D1;+0:11]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[c:5]:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10]:1 | 17.8 | [{"value": 17.8, "product": "IC1=CC=C2C(NC=NC2=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 10 | MINUTE | 7-Amino-quinazolin-4-one (R. Dempsy and E. Skito, Biochemistry, 30, 1991, 8480) (1.61 g) was suspended in 6N HCl (20 ml) and cooled in an ice bath. A solution of sodium nitrite (0.75 g) in water (10 ml) was added dropwise over 15 minutes. After a further 10 minutes, a solution of potassium iodide (1.66 g) in water (5 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2cncnc2c1 | c1ccc2cncnc2c1 | c1ccc2cncnc2c1 | Other | O.Cl | 20 | 0.166667 | Nc1ccc2c(=O)[nH]cnc2c1.[I-]>O.Cl>O=c1[nH]cnc2cc(I)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1ca761a1bcfc4116b249e92d5f7ee400 | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2cc(I)ccc12>>Clc1ncnc2cc(I)ccc12 | IC1=CC=C2C(NC=NC2=C1)=O.P(=O)(Cl)(Cl)Cl>>ClC1=NC=NC2=CC(=CC=C12)I | O=P(Cl)(Cl)[Cl:1].O=[c:2]1[nH:3][cH:4][n:5][c:6]2[cH:7][c:8]([I:9])[cH:10][cH:11][c:12]12>>[Cl:1][c:2]1[n:3][cH:4][n:5][c:6]2[cH:7][c:8]([I:9])[cH:10][cH:11][c:12]12 | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2cc(I)ccc12 | Clc1ncnc2cc(I)ccc12 | null | null | null | Functional Group Interconversion | OtherReaction | 5d38f97f3712b237e9f3fba95a694ccb97b6e400bb6127459a74d91e2bc1ab18 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ncncc2c1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | null | null | null | null | 7-Iodoquinazolin-4-one (0.46 g) was treated with phosphorous oxychloride (5 ml) at reflux under nitrogen for 2 hours. The mixture was cooled, evaporated and partitioned between saturated aqueous sodium carbonate and ethyl acetate. The organic phase was dried and concentrated in vacuo to give the title compound (0.43 g)... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2cncnc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HCl | null | null | null | O=P(Cl)(Cl)Cl.O=c1[nH]cnc2cc(I)ccc12>>Clc1ncnc2cc(I)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c2342eecc704ff9bc874cc3b0f75bf2 | Nc1cc(F)ccc1C(=O)O>>Nc1cc(F)c(I)cc1C(=O)O | I(=O)(=O)Cl.I(=O)(=O)Cl.C(C1=CC=CC=C1)[N+](C)(C)C.ClCCl.NC1=C(C(=O)O)C=CC(=C1)F.C(O)([O-])=O.[Na+]>>NC1=C(C(=O)O)C=C(C(=C1)F)I | [NH2:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:8][c:9]1[C:10](=[O:11])[OH:12]>>[NH2:1][c:2]1[cH:3][c:4]([F:5])[c:6]([I:7])[cH:8][c:9]1[C:10](=[O:11])[OH:12] | Nc1cc(F)ccc1C(=O)O | Nc1cc(F)c(I)cc1C(=O)O | null | null | CO | Functional Group Addition | Aromatic iodination | 2e63a9b91d60f82a8e59b7c72ed55b9aec048f26be2f5eb9ca65b1b73867743c | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1ccccc1 | [F;D1;H0:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[F;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[I;D1;H0:10]):[c:5]:[c:6]-[C:7](=[O;D1;H0:8])-[O;D1;H1:9] | 77 | [{"value": 77.0, "product": "NC1=C(C(=O)O)C=C(C(=C1)F)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.0, "product": "NC1=C(C(=O)O)C=C(C(=C1)F)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | To a vigorously stirred solution of dichloromethane (700 ml), methanol (320 ml), and 2-amino-4-fluoro-benzoic acid (33.35 grams, 215 mmoles) was added solid sodium hydrogencarbonate (110 grams, 1.31 moles) followed by portion addition of benzyltrimethyl ammonium dichloroiodate (82.5 grams, 237 mmoles). The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CO | null | 48 | Nc1cc(F)ccc1C(=O)O>CO>Nc1cc(F)c(I)cc1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0bc8ffdbbaca41bcbaf4c615964c8a93 | Nc1cc(F)c(I)cc1C(=O)O.O=C(Cl)OC(Cl)(Cl)Cl>>O=c1[nH]c2cc(F)c(I)cc2c(=O)o1 | NC1=C(C(=O)O)C=C(C(=C1)F)I.ClC(Cl)(Cl)OC(=O)Cl>>FC=1C=C2C(C(=O)OC(N2)=O)=CC1I | [NH2:3][c:4]1[cH:5][c:6]([F:7])[c:8]([I:9])[cH:10][c:11]1[C:12](=[O:13])[OH:14].ClC(Cl)(Cl)O[C:2](Cl)=[O:1]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]([F:7])[c:8]([I:9])[cH:10][c:11]2[c:12](=[O:13])[o:14]1 | Nc1cc(F)c(I)cc1C(=O)O.O=C(Cl)OC(Cl)(Cl)Cl | O=c1[nH]c2cc(F)c(I)cc2c(=O)o1 | null | null | O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | fc15380ff4d79ccb35bf3855432af73f82f5e67c05b3e399eb4e4e9fc738479c | 1d99fb7140022ceb276e15a64139fff14e6daa2ce5fade57cf77a9575a5ee61e | O=c1[nH]c2ccccc2c(=O)o1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-Cl.[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6](-[C;H0;D3;+0:7](=[O;D1;H0:8])-[OH;D1;+0:9]):[c:10]>>[O;D1;H0:8]=[c;H0;D3;+0:7]1:[o;H0;D2;+0:9]:[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:3]:[c:4](:[c:5]):[c:6]:1:[c:10] | 90.4 | [{"value": 90.0, "product": "FC=1C=C2C(C(=O)OC(N2)=O)=CC1I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.4, "product": "FC=1C=C2C(C(=O)OC(N2)=O)=CC1I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Anhydrous dioxane (0.5 litres), 2-amino-4-fluoro-5-iodo-benzoic acid (46 grams, 164 mmoles), and trichloromethylchloroformate (97.4 grams, 492 mmoles) were added to a one litre one neck flask equipped with a magnetic stir bar and reflux condenser. The solution was placed under anhydrous nitrogen, stirred and heated to ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trichloro group.Carboxylic acid.Ether.Primary amine | null | c1ccccc1 | c1ccc2ncocc2c1 | c1ccc2ncocc2c1 | HCl | O1CCOCC1 | null | null | Nc1cc(F)c(I)cc1C(=O)O.O=C(Cl)OC(Cl)(Cl)Cl>O1CCOCC1>O=c1[nH]c2cc(F)c(I)cc2c(=O)o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0d4cdbe90b8748d0ab8949e429a5dc83 | N=CN.O=c1[nH]c2cc(F)c(I)cc2c(=O)o1>>Oc1ncnc2cc(F)c(I)cc12 | FC=1C=C2C(C(=O)OC(N2)=O)=CC1I.C(C)(=O)O.C(=N)N>>OC1=NC=NC2=CC(=C(C=C12)I)F | NC=[NH:3].O=[c:4]1o[c:2](=[O:1])[c:13]2[c:6]([nH:5]1)[cH:7][c:8]([F:9])[c:10]([I:11])[cH:12]2>>[OH:1][c:2]1[n:3][cH:4][n:5][c:6]2[cH:7][c:8]([F:9])[c:10]([I:11])[cH:12][c:13]12 | N=CN.O=c1[nH]c2cc(F)c(I)cc2c(=O)o1 | Oc1ncnc2cc(F)c(I)cc12 | null | null | CN(C=O)C | Miscellaneous | OtherReaction | 1838aa909a592eab94589c7b043b2a6a39303e9443aeb018fb34fd1bc651fb9a | cd196a3cba60b08ae897e4a23847dffdb90adc6b09740a5f115e8d6d87cf6580 | c1ccc2ncncc2c1 | N-C=[NH;D1;+0:1].O=[c;H0;D3;+0:2]1:[nH;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:7]):[c;H0;D3;+0:8](=[O;H0;D1;+0:9]):o:1>>[OH;D1;+0:9]-[c;H0;D3;+0:8]1:[n;H0;D2;+0:1]:[cH;D2;+0:2]:[n;H0;D2;+0:3]:[c:4](:[c:5]):[c:6]:1:[c:7] | 91.2 | [{"value": 91.0, "product": "OC1=NC=NC2=CC(=C(C=C12)I)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "OC1=NC=NC2=CC(=C(C=C12)I)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | Dimethylformamide (0.5 litres), 4-fluoro-5-iodo-isatoic anhydride (45 grams, 147 mmoles), and formamidine acetate (45.92 grams, 441 mmoles), were combined in a one litre one-neck flask fitted with a magnetic stir bar. The mixture was placed under anhydrous nitrogen and heated at 110° C. for 6 hours. The mixture was all... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic alcohol | c1ccc2ncocc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HO- | CN(C=O)C | 110 | null | N=CN.O=c1[nH]c2cc(F)c(I)cc2c(=O)o1>CN(C=O)C>Oc1ncnc2cc(F)c(I)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8c6e643ef7e94b1798220fa7e7df48ce | O=Cc1csc(Br)n1.OCCO>>Brc1nc(C2OCCO2)cs1 | BrC=1SC=C(N1)C=O.C(CO)O>>BrC=1SC=C(N1)C1OCCO1 | O=[CH:5][c:4]1[n:3][c:2]([Br:1])[s:11][cH:10]1.[OH:6][CH2:7][CH2:8][OH:9]>>[Br:1][c:2]1[n:3][c:4]([CH:5]2[O:6][CH2:7][CH2:8][O:9]2)[cH:10][s:11]1 | O=Cc1csc(Br)n1.OCCO | Brc1nc(C2OCCO2)cs1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | fe0fbb45a87f24c1e456c6b4e41101562cd8f0af3ec376bb6115e7c1555d997b | 7ac65b5a5f576337ce8e86e0130eb9b4757ca21b2419a0e82bbdfd5def30ee73 | c1nc(C2OCCO2)cs1 | O=[CH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#16;a:5]:[c:6]:1.[OH;D1;+0:7]-[C:8]-[C:9]-[OH;D1;+0:10]>>[#16;a:5]1:[c:6]:[c:2](-[CH;D3;+0:1]2-[O;H0;D2;+0:7]-[C:8]-[C:9]-[O;H0;D2;+0:10]-2):[#7;a:3]:[c:4]:1 | 74.7 | [{"value": 74.7, "product": "BrC=1SC=C(N1)C1OCCO1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Bromothiazole-4-carbaldehyde (6.56 g, 34.17 mmol) [A. T. Ung, S. G. Pyne/Tetrahedron: Asymmetry 9 (1998) 1395–1407] and ethylene glycol (5.72 ml, 102.5 mmol) were heated under reflux in toluene (50 ml), with a Dean and Stark trap fitted, for 18 hr. The product was concentrated and purified by column chromatography (1... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCO1 | c1cscn1.C1COCO1 | HO- | C1(=CC=CC=C1)C | null | null | O=Cc1csc(Br)n1.OCCO>C1(=CC=CC=C1)C>Brc1nc(C2OCCO2)cs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8f9cade0188a4427a37fc2196adc5311 | Brc1nc(C2OCCO2)cs1.CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC>>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1scnc1C1OCCO1 | C(CCC)[Sn](CCCC)(CCCC)Cl.C(CCC)[Li].CCCCCC.BrC=1SC=C(N1)C1OCCO1>>O1C(OCC1)C=1N=CSC1[Sn](CCCC)(CCCC)CCCC | Br[c:16]1[s:15][cH:14][c:18]([CH:19]2[O:20][CH2:21][CH2:22][O:23]2)[n:17]1.[Cl][Sn:5]([CH2:4][CH2:3][CH2:2][CH3:1])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][Sn:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][CH2:11][CH2:12][CH3:13])[c:14]1[s:15][cH:16][n:17][c:18]1[CH:19]1[O... | Brc1nc(C2OCCO2)cs1.CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1scnc1C1OCCO1 | null | null | C1CCOC1.O | Miscellaneous | OtherReaction | 8ae5fc7f9b4acc2fe8513c129e6d51d0ca2d3187413857a77607588f36f1db43 | 31a273782785992494eb6bb26e7d587fea5a029768e25f39f813b72e5d926c19 | c1nc(C2OCCO2)cs1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[cH;D2;+0:3]:[c:4](-[C:5](-[#8:6])-[#8:7]):[#7;a:8]:1.[C:9]-[C:10]-[Sn;H0;D4;+0:11](-[Cl])(-[C:12]-[C:13])-[C:14]-[C:15]>>[#8:6]-[C:5](-[c:4]1:[#7;a:8]:[cH;D2;+0:1]:[#16;a:2]:[c;H0;D3;+0:3]:1-[Sn;H0;D4;+0:11](-[C:10]-[C:9])(-[C:12]-[C:13])-[C:14]-[C:15])-[#8:7] | 98.1 | [{"value": 98.1, "product": "O1C(OCC1)C=1N=CSC1[Sn](CCCC)(CCCC)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Bromo-4-(1,3-dioxolan-2-yl) thiazole (6.4 g ,27.14 mmol) was stirred at −78° C. in dry THF (38 ml). 1.6M n butyl lithium in hexane (18.6 ml, 29.78 mmol) was added dropwise under nitrogen. After 30 min at this temperature, tributyl tin chloride (7.35 ml, 27.14 mmol) was added dropwise. The reaction was allowed to warm... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | Tin | c1cscn1 | c1cscn1 | c1cscn1.C1COCO1 | Br- | C1CCOC1.O | null | null | Brc1nc(C2OCCO2)cs1.CCC[CH2][Sn]([Cl])([CH2]CCC)[CH2]CCC>C1CCOC1.O>CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1scnc1C1OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a8e6fc294c5542ca964ef4ec188a5778 | Clc1ncnc2ccc(I)cc12.Nc1ccc(OCc2ccccc2)cc1>>Cl.Ic1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2c1 | ClC1=NC=NC2=CC=C(C=C12)I.C(C1=CC=CC=C1)OC1=CC=C(N)C=C1>>Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC=C(C=C12)I | [Cl:1][c:10]1[n:9][cH:8][n:7][c:6]2[cH:5][cH:4][c:3]([I:2])[cH:27][c:26]21.[NH2:11][c:12]1[cH:13][cH:14][c:15]([O:16][CH2:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][cH:25]1>>[ClH:1].[I:2][c:3]1[cH:4][cH:5][c:6]2[n:7][cH:8][n:9][c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([O:16][CH2:17][c:18]4[cH:19][cH:20][cH:... | Clc1ncnc2ccc(I)cc12.Nc1ccc(OCc2ccccc2)cc1 | Cl.Ic1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4ccccc34)cc2)cc1 | [Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[ClH;D0;+0:1].[c:12]:[c:11](-[NH;D2;+0:10]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]):[c:13] | 97.4 | [{"value": 97.4, "product": "Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC=C(C=C12)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Chloro-6-iodoquinazoline (8 g) was treated with 4-benzyloxyaniline (5.5 g) in acetonitrile (500 ml) at reflux under N2 for 18 hours. Subsequent cooling and filtration gave the title compound (13.13 g); δH [2H6]-DMSO 11.45 (1H, b, NH), 9.22 (1H, s, 5-H), 8.89 (1H, s, 2-H), 8.36 (1H, d, 7-H), 7.69 (1H, d, 8-H), 7.63 (2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | null | C(C)#N | null | null | Clc1ncnc2ccc(I)cc12.Nc1ccc(OCc2ccccc2)cc1>C(C)#N>Cl.Ic1ccc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce0a4ccfcaef4b198680731b618331df | Fc1cc2ncnc(Cl)c2cc1I.Nc1ccc(OCc2ccccc2)cc1>>Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I | Cl.ClC1=NC=NC2=CC(=C(C=C12)I)F.O1CCOCC1.Cl.C(C1=CC=CC=C1)OC1=CC=C(N)C=C1>>Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)I)F | Cl[c:9]1[n:8][cH:7][n:6][c:5]2[cH:4][c:3]([F:2])[c:27]([I:28])[cH:26][c:25]21.[NH2:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[cH:23][cH:24]1>>[F:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][c:14]([O:15][CH2:16][c:17]4[cH:18][cH:19][cH:20][cH:21][c... | Fc1cc2ncnc(Cl)c2cc1I.Nc1ccc(OCc2ccccc2)cc1 | Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I | null | null | ClCCl | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4ccccc34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[c:11]:[c:10](-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8]):[c:12] | 79.1 | [{"value": 79.0, "product": "Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)I)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.1, "product": "Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)I)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | Prepared according to Procedure A from 4-chloro-6-iodo-7-fluoro-quinazoline hydrochloride (4.02 grams, 11.65 mmoles), anhydrous dioxane (70 ml), dichloromethane (20 ml) and 4-benzyloxyaniline hydrochloride (2.83 grams, 12 mmoles). The mixture was stirred and heated to 110° C. (oil bath temperature) for 16 hours. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1 | HCl | ClCCl | 110 | null | Fc1cc2ncnc(Cl)c2cc1I.Nc1ccc(OCc2ccccc2)cc1>ClCCl>Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5fb41e082e254b2c9a8820aac25dfc35 | Clc1cc2c(Cl)ncnc2cn1.Nc1ccc(OCc2ccccc2)cc1>>Clc1cc2c(Nc3ccc(OCc4ccccc4)cc3)ncnc2cn1 | C(C1=CC=CC=C1)OC1=CC=C(N)C=C1.ClC=1C2=C(N=CN1)C=NC(=C2)Cl>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC=1C2=C(N=CN1)C=NC(=C2)Cl | Cl[c:5]1[c:4]2[cH:3][c:2]([Cl:1])[n:26][cH:25][c:24]2[n:23][cH:22][n:21]1.[NH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[cH:19][cH:20]1>>[Cl:1][c:2]1[cH:3][c:4]2[c:5]([NH:6][c:7]3[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]4[cH:14][cH:15][cH:16][cH:17][cH:18]4)[cH:19][cH:20]3)[n:2... | Clc1cc2c(Cl)ncnc2cn1.Nc1ccc(OCc2ccccc2)cc1 | Clc1cc2c(Nc3ccc(OCc4ccccc4)cc3)ncnc2cn1 | null | null | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | d7e80981ec4355d1692da3210ded123ee4151f1f202c481ca7dd6b10037b54ac | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cnccc34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[c:13]:[c:12](-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:1):[c:14] | null | [] | null | null | null | null | Prepared according to Procedure A from 4-benzyloxyaniline (1 eq) and 4,6-dichloro-pyrido[3,4-d]pyrimidine (1 eq); δH (CDCl3) 9.11 (1H, s), 8.78 (1H, s), 7.75 (1H, d), 7.56 (2H, dd), 7.40 (5H, m), 7.15 (2H, d), 5.10 (2H, s); m/z (M+1)+409.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cc2cncnc2cn1 | c1cc2cncnc2cn1 | c1ccccc1.c1ccccc1.c1cc2cncnc2cn1 | HCl | null | null | null | Clc1cc2c(Cl)ncnc2cn1.Nc1ccc(OCc2ccccc2)cc1>>Clc1cc2c(Nc3ccc(OCc4ccccc4)cc3)ncnc2cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8b3bea1d833140cf9b8c1582932f75e3 | Clc1cc2c(Cl)ncnc2cn1.Nc1ccc(OCc2cccc(F)c2)cc1>>Fc1cccc(COc2ccc(Nc3ncnc4cnc(Cl)cc34)cc2)c1 | ClC=1C2=C(N=CN1)C=NC(=C2)Cl.FC=1C=C(COC2=CC=C(N)C=C2)C=CC1>>ClC1=CC2=C(N=CN=C2NC2=CC=C(C=C2)OCC2=CC(=CC=C2)F)C=N1 | Cl[c:14]1[n:15][cH:16][n:17][c:18]2[cH:19][n:20][c:21]([Cl:22])[cH:23][c:24]12.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:25][cH:26]2)[cH:27]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([NH:13][c:14]3[n:15][cH:16][n:17][c:18]4[cH:19][n:20][c:21... | Clc1cc2c(Cl)ncnc2cn1.Nc1ccc(OCc2cccc(F)c2)cc1 | Fc1cccc(COc2ccc(Nc3ncnc4cnc(Cl)cc34)cc2)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | d7e80981ec4355d1692da3210ded123ee4151f1f202c481ca7dd6b10037b54ac | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(COc2ccc(Nc3ncnc4cnccc34)cc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:1.[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[c:13]:[c:12](-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:1):[c:14] | null | [] | null | null | null | null | 4,6-Dichloro-pyrido[3,4-d]pyrimidine (1 g) and 4-(3-fluorobenzyloxy)aniline (1.08 g) in acetonitrile (70 ml) were reacted together as in Procedure A. The product was collected by filtration as a yellow solid (1.86 g); m/z 381 (M+1)+.
Conditions: See reaction.notes.procedure_details.
Workup: The product was collected by... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cc2cncnc2cn1 | c1cc2cncnc2cn1 | c1ccccc1.c1ccccc1.c1cc2cncnc2cn1 | HCl | C(C)#N | null | null | Clc1cc2c(Cl)ncnc2cn1.Nc1ccc(OCc2cccc(F)c2)cc1>C(C)#N>Fc1cccc(COc2ccc(Nc3ncnc4cnc(Cl)cc34)cc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8d8f1c75637248039f15ee802bde1ef1 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Clc1cc2c(Nc3ccc(OCc4ccccc4)cc3)ncnc2cn1>>O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5ccccc5)cc4)ncnc3cn2)o1 | C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC=1C2=C(N=CN1)C=NC(=C2)Cl.O1C(OCC1)C1=CC=C(O1)[Sn](CCCC)(CCCC)CCCC>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC=1C2=C(N=CN1)C=NC(=C2)C2=CC=C(O2)C=O | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:6]1[cH:5][cH:4][c:3]([CH:2]2OCC[O:1]2)[o:32]1.Cl[c:7]1[cH:8][c:9]2[c:10]([NH:11][c:12]3[cH:13][cH:14][c:15]([O:16][CH2:17][c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[cH:24][cH:25]3)[n:26][cH:27][n:28][c:29]2[cH:30][n:31]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Clc1cc2c(Nc3ccc(OCc4ccccc4)cc3)ncnc2cn1 | O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5ccccc5)cc4)ncnc3cn2)o1 | null | null | Cl | Acylation | OtherReaction | cdcdbab2b874eab9bcd20f9243c192f8716be48b5b517ff2a103a9676e9c5a97 | f78ef97212accf10523047d1c7ef9c894dcd3eff344da65f910d057d1373fa81 | c1ccc(COc2ccc(Nc3ncnc4cnc(-c5ccco5)cc34)cc2)cc1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3](-[CH;D3;+0:4]2-O-C-C-[O;H0;D2;+0:5]-2):[c:6]:[c:7]:1.Cl-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10]:[c:11](:[#7;a:12]):[c:13](:[c:14]:[#7;a:15]):[c:16]:1>>[#7;a:15]:[c:14]:[c:13]1:[c:16]:[c;H0;D3;+0:8](-[c;H0;D3;+0:1]2:[#8;a:2]:[c:3](-[CH;D2;+0:4]=[O;H0;D1... | 52 | [{"value": 52.0, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC=1C2=C(N=CN1)C=NC(=C2)C2=CC=C(O2)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 51.9, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC=1C2=C(N=CN1)C=NC(=C2)C2=CC=C(O2)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | (4-Benzyloxyphenyl)-(6-chloro-pyrido[3,4-d]pyrimidin-4-yl)-amine (4.0 g, 11.0 mmol), 5-(1,3-dioxolan-2-yl)-2-(tributylstannyl)furan (J. Chem. Soc., Chem. Commun., (1988), 560) (6.0 g, 14.0 mmol) were reacted together in a procedure analogous to Procedure B above for 20 hrs. The reaction mixture was allowed to cool, 1N ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Tin | Aldehyde | c1ccoc1.C1COCO1.c1cc2cncnc2cn1 | c1ccoc1.c1cc2cncnc2cn1 | c1ccoc1.c1ccccc1.c1ccccc1.c1cc2cncnc2cn1 | HCl.Sn | Cl | null | 0.25 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Clc1cc2c(Nc3ccc(OCc4ccccc4)cc3)ncnc2cn1>Cl>O=Cc1ccc(-c2cc3c(Nc4ccc(OCc5ccccc5)cc4)ncnc3cn2)o1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2ed2edacb0cb469abc1fae984ae033a0 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I>>Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1 | Cl.C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)I)F.O1C(OCC1)C1=CC=C(O1)[Sn](CCCC)(CCCC)CCCC.C(C)(C)N(CC)C(C)C>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)C=1OC(=CC1)C1OCCO1)F | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:27]1[cH:28][cH:29][c:30]([CH:31]2[O:32][CH2:33][CH2:34][O:35]2)[o:36]1.I[c:26]1[c:2]([F:1])[cH:3][c:4]2[n:5][cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([O:14][CH2:15][c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21]4)[cH:22][cH:23]3)[c:24]2[cH:25]1>>[F:1][c:2]1[cH:3][c:4]2[n:5][cH:6][... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I | Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1 | null | null | CN(C)C=O | C-C Coupling | Stille reaction_aryl | e0837286282948e252601463def8f2065b37315796eaf567e28dfdae8becb931 | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | c1ccc(COc2ccc(Nc3ncnc4ccc(-c5ccc(C6OCCO6)o5)cc34)cc2)cc1 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1.I-[c;H0;D3;+0:6]1:[c:7]:[c:8](:[c:9]:[#7;a:10]):[c:11](:[#7;a:12]):[c:13]:[c:14]:1-[F;D1;H0:15]>>[#7;a:12]:[c:11]1:[c:13]:[c:14](-[F;D1;H0:15]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1]2:[#8;a:2]:[c:3]:[c:4]:[c:5]:2):[c:7]:[c:8]:1:[c:9]:[#7;... | 59.4 | [{"value": 59.0, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)C=1OC(=CC1)C1OCCO1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.4, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)NC1=NC=NC2=CC(=C(C=C12)C=1OC(=CC1)C1OCCO1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 4 | HOUR | Synthesized according to Procedure B from a solution of (4-benzyloxyphenyl)-(6-iodo-7-fluoro-quinazolin-4-yl)-amine hydrochloride (508 mg, 1 mmole), 5-(1,3-dioxolan-2-yl)-2-(tributylstannyl)furan (645 mg, 1.5 mmole), diisopropylethyl amine (650 mg, 5 mmole), and dichlorobis(triphenylphosphine) palladium (140 mg, 0.2 mm... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1ccoc1.c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccoc1 | c1ccc2ncncc2c1.c1ccccc1.c1ccccc1.c1ccoc1.C1COCO1 | HI.Sn | CN(C)C=O | 100 | 4 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1ccc(C2OCCO2)o1.Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1I>CN(C)C=O>Fc1cc2ncnc(Nc3ccc(OCc4ccccc4)cc3)c2cc1-c1ccc(C2OCCO2)o1 |
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