dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4d55731c11f64cea9f07bcf59e7d1826 | Cc1c(O)cccc1O.O=C1OC(=O)c2ccccc21>>Cc1c(O)ccc(C(=O)c2ccccc2C(=O)O)c1O | [Cl-].[Al+3].[Cl-].[Cl-].C1(C=2C(C(=O)O1)=CC=CC2)=O.OC1=C(C(=CC=C1)O)C>>OC1=C(C(=O)C2=C(C(=O)O)C=CC=C2)C=CC(=C1C)O | [CH3:1][c:2]1[c:3]([OH:4])[cH:5][cH:6][cH:7][c:19]1[OH:20].[C:8]1(=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16](=[O:17])[O:18]1>>[CH3:1][c:2]1[c:3]([OH:4])[cH:5][cH:6][c:7]([C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16](=[O:17])[OH:18])[c:19]1[OH:20] | Cc1c(O)cccc1O.O=C1OC(=O)c2ccccc21 | Cc1c(O)ccc(C(=O)c2ccccc2C(=O)O)c1O | null | null | ClCCl.ClCC(Cl)(Cl)Cl.C(C)(=O)OCC | C-C Coupling | OtherReaction | 8cdd0ddbe4a96a0e39dccfa37b4ea678b3d4a1fc9b3adf6c3819d3c2573775f2 | 866970e08f314f31ffc47d6eb535bcb1752d0b777915aef3e10fc0b2f15e8faf | O=C(c1ccccc1)c1ccccc1 | [O;D1;H0:1]=[C:2]1-[O;H0;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8]-1.[O;D1;H1:9]-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]:[c:14]>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[c:8]:[c:6](-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:10](-[O;D1;H1:9]):[c:11]):[c:7] | 42.2 | [{"value": 42.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.2, "product": null, "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Aluminum chloride (21.4 g, 161 mmol) was added to a stirring suspension of phthalic anhydride (6 g, 40 mmol) in tetrachloroethane (200 mL) under nitrogen. 1,3-Dihydroxy-2-methylbenzene (5 g, 40 mmol) was added and the mixture quickly thickened. After the precipitates were broken up with a spatula the reaction continued... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester | Carboxylic acid.Ketone | c1ccccc1.c1ccc2c(c1)COC2 | c1ccccc1 | c1ccccc1.c1ccccc1 | null | ClCCl.ClCC(Cl)(Cl)Cl.C(C)(=O)OCC | null | 1 | Cc1c(O)cccc1O.O=C1OC(=O)c2ccccc21>ClCCl.ClCC(Cl)(Cl)Cl.C(C)(=O)OCC>Cc1c(O)ccc(C(=O)c2ccccc2C(=O)O)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ddbb201535134dad8e2a408140bc94af | CC1CC2=C(C1)S(=O)c1cccc(-c3ccccc3)c12>>CC1=Cc2sc3cccc(-c4ccccc4)c3c2C1 | O.CC1CC2=C(C3=C(S2=O)C=CC=C3C3=CC=CC=C3)C1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C1(=CC=C(C=C1)S(=O)(=O)O)C>>CC1=CC2=C(C3=C(S2)C=CC=C3C3=CC=CC=C3)C1 | O=[S:5]1[C:4]2=[C:18]([c:17]3[c:6]1[cH:7][cH:8][cH:9][c:10]3-[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[CH2:19][CH:2]([CH3:1])[CH2:3]2>>[CH3:1][C:2]1=[CH:3][c:4]2[s:5][c:6]3[cH:7][cH:8][cH:9][c:10](-[c:11]4[cH:12][cH:13][cH:14][cH:15][cH:16]4)[c:17]3[c:18]2[CH2:19]1 | CC1CC2=C(C1)S(=O)c1cccc(-c3ccccc3)c12 | CC1=Cc2sc3cccc(-c4ccccc4)c3c2C1 | null | null | C1(=CC=CC=C1)C.C(C)OCC.C1CCOC1 | Oxidation | OtherReaction | 2e5b14f70bab3e92f0ae613379a343a11ac7267944a98a7b82eea4907067f05f | ec34655623154235bb8bc8c5d69eb54231762db22a4ef09b3b1ceac23d093bb8 | C1=Cc2sc3cccc(-c4ccccc4)c3c2C1 | O=[S;H0;D3;+0:1]1-[C;H0;D3;+0:2]2=[C;H0;D3;+0:3](-[C:4]-[CH;D3;+0:5](-[C;D1;H3:6])-[CH2;D2;+0:7]-2)-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C;D1;H3:6]-[C;H0;D3;+0:5]1=[CH;D2;+0:7]-[c;H0;D3;+0:2]2:[s;H0;D2;+0:1]:[c:10](:[c:11]):[c:8](:[c:9]):[c;H0;D3;+0:3]:2-[C:4]-1 | null | [] | null | null | 4 | HOUR | A solution of 81.4 g of 2-methyl-8-phenyl-1,2-dihydrobenzo[b]cyclopenta[d]thiophenone (0.29 mol) (1a) in 800 ml of THF was admixed at 0° C. with 225 ml of a 1.0 molar solution of lithium aluminum hydride (0.23 mol) in diethyl ether. The mixture was stirred at room temperature for another 4 hours. 25 ml of water were th... | 10.6084/m9.figshare.5104873.v1 | null | Sulfoxide | null | c1ccc2c3c(sc2c1)CCC3 | C1=Cc2sc3ccccc3c2C1 | C1=Cc2sc3ccccc3c2C1.c1ccccc1 | HO- | C1(=CC=CC=C1)C.C(C)OCC.C1CCOC1 | null | 4 | CC1CC2=C(C1)S(=O)c1cccc(-c3ccccc3)c12>C1(=CC=CC=C1)C.C(C)OCC.C1CCOC1>CC1=Cc2sc3cccc(-c4ccccc4)c3c2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ddc6f8d40731455e8ef752e5ae687e4a | Cc1ccc(CC(C#N)Cc2ccccc2)cc1.Cc1ccc(CCl)cc1>>Cc1ccc(CC(C#N)(Cc2ccc(C)cc2)c2ccc(C)cc2)cc1 | C1(=CC=CC=C1)C.CC1=CC=C(C=C1)CC(C#N)CC1=CC=CC=C1.[C-]#N.[Na+].C1(=CC=CC=C1)C.CC1=CC=C(CCl)C=C1>>CC1=CC=C(C=C1)CC(C#N)(CC1=CC=C(C=C1)C)C1=CC=C(C=C1)C | [cH:2]1[cH:3][cH:4][c:5]([CH2:6][CH:7]([C:8]#[N:9])[CH2:10][c:11]2[cH:12][cH:13][c:14]([CH3:15])[cH:16][cH:17]2)[cH:25][cH:26]1.ClC[c:18]1[cH:19][cH:20][c:21]([CH3:22])[cH:23][cH:24]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][C:7]([C:8]#[N:9])([CH2:10][c:11]2[cH:12][cH:13][c:14]([CH3:15])[cH:16][cH:17]2)[c:18]2[cH:19][cH... | Cc1ccc(CC(C#N)Cc2ccccc2)cc1.Cc1ccc(CCl)cc1 | Cc1ccc(CC(C#N)(Cc2ccc(C)cc2)c2ccc(C)cc2)cc1 | null | null | [OH-].[Na+] | C-C Coupling | OtherReaction | 88715193b4a8cb255fc607587ae7f05df300e25d320e8587aedf2525904dcb9f | f5e5e22797736d188bba28deb76a4cee8e4fee4dca04fe24f733d2ee68a23361 | c1ccc(CC(Cc2ccccc2)c2ccccc2)cc1 | Cl-C-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[N;D1;H0:6]#[C:7]-[CH;D3;+0:8](-[C:9]-[c:10])-[C:11]-[c:12]1:[c:13]:[c:14]:[cH;D2;+0:15]:[c:16]:[c:17]:1>>[C;D1;H3:18]-[c;H0;D3;+0:15]1:[c:14]:[c:13]:[c:12](-[C:11]-[C;H0;D4;+0:8](-[C:9]-[c:10])(-[C:7]#[N;D1;H0:6])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:17]:[c:16]:1 | null | [] | 40 | CELSIUS | 48 | HOUR | Part b. Preparation of 4-Methyl-(α-(4-methylphenyl)-(α-[(4-methylphenyl)methyl]-benzenepropanenitrile: A flask containing 1.0 g (2 mmol) of sodium cyanide (95%) dissolved in 5 mL of 50% NaOH aqueous solution is charged with 0.3 g silica catalyst, followed by 4-methylbenzyl chloride (6.8 mmol) and 1 mL toluene. The flas... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | [OH-].[Na+] | 40 | 48 | Cc1ccc(CC(C#N)Cc2ccccc2)cc1.Cc1ccc(CCl)cc1>[OH-].[Na+]>Cc1ccc(CC(C#N)(Cc2ccc(C)cc2)c2ccc(C)cc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fdaf0a98c11b4a719b9bfd0aefb8ab0c | COC(=O)CCC[N+](=O)[O-].N>>NC(=O)CCC[N+](=O)[O-] | [N+](=O)([O-])CCCC(=O)OC.N>>[N+](=O)([O-])CCCC(=O)N | CO[C:2](=[O:3])[CH2:4][CH2:5][CH2:6][N+:7](=[O:8])[O-:9].[NH3:1]>>[NH2:1][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][N+:7](=[O:8])[O-:9] | COC(=O)CCC[N+](=O)[O-].N | NC(=O)CCC[N+](=O)[O-] | null | null | CO | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH3;D0;+0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 78 | [{"value": 78.0, "product": "[N+](=O)([O-])CCCC(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | To a solution of methyl 4-nitrobutyrate (8.83 g, 60 mmol) in methanol (20 mL) at 0° C. was added a solution of ammonia in methanol (7N, 30 mL). The solution was then warmed to room temperature and stirred at for 72 h. The solvent was evaporated and the residue was re-crystallized from ethyl acetate to give the title pr... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | null | HO- | CO | null | 72 | COC(=O)CCC[N+](=O)[O-].N>CO>NC(=O)CCC[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d9eda4e4a48c457d943cfce1a204eb25 | NC(=O)CCC[N+](=O)[O-].OCCF>>NC(=O)CCC(C(O)CF)[N+](=O)[O-] | FCCO.[N+](=O)([O-])CCCC(=O)N.C(C(=O)Cl)(=O)Cl.CS(=O)C>>FCC(C(CCC(=O)N)[N+](=O)[O-])O | [NH2:1][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][N+:11](=[O:12])[O-:13].[CH2:7]([OH:8])[CH2:9][F:10]>>[NH2:1][C:2](=[O:3])[CH2:4][CH2:5][CH:6]([CH:7]([OH:8])[CH2:9][F:10])[N+:11](=[O:12])[O-:13] | NC(=O)CCC[N+](=O)[O-].OCCF | NC(=O)CCC(C(O)CF)[N+](=O)[O-] | null | null | ClCCl.CCN(CC)CC.C(Cl)Cl.C1CCOC1 | C-C Coupling | OtherReaction | a76739cb57e2584c86ca56ae2e25a18c069d633832049c5e8d43eaf1c7ff6072 | 9fa23f1768d037fcd2a30655674d1b20d68d9c34d67b82adb67ad3f0e3eeac7e | null | [F;D1;H0:1]-[C:2]-[CH2;D2;+0:3]-[O;D1;H1:4].[N;D1;H2:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[CH2;D2;+0:10]-[#7;+:11](-[O;-;D1;H0:12])=[O;D1;H0:13]>>[F;D1;H0:1]-[C:2]-[CH;D3;+0:3](-[O;D1;H1:4])-[CH;D3;+0:10](-[C:9]-[C:8]-[C:6](-[N;D1;H2:5])=[O;D1;H0:7])-[#7;+:11](-[O;-;D1;H0:12])=[O;D1;H0:13] | 41.2 | [{"value": 41.0, "product": "FCC(C(CCC(=O)N)[N+](=O)[O-])O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.2, "product": "FCC(C(CCC(=O)N)[N+](=O)[O-])O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | To a solution of oxalyl chloride (5.29 g, 41.4 mmol) in anhydrous dichloromethane (30 mL) at −78° C. was added anhydrous DMSO (6.2 mL, 87.4 mmol) dropwise with stirring in such a rate that the temperature was kept at −50 to −60° C. The solution was stirred for 15 min, then 2-fluoroethanol (1.62 mL, 27.6 mmol) was added... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary alcohol | Nitro group.Secondary alcohol | null | null | null | null | ClCCl.CCN(CC)CC.C(Cl)Cl.C1CCOC1 | 0 | null | NC(=O)CCC[N+](=O)[O-].OCCF>ClCCl.CCN(CC)CC.C(Cl)Cl.C1CCOC1>NC(=O)CCC(C(O)CF)[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e3c4ef72c9b34055b5a306d0ac722329 | NC(=O)CCC(C(O)CF)[N+](=O)[O-]>>NC(=O)CCC(N)C(O)CF | FCC(C(CCC(=O)N)[N+](=O)[O-])O>>NC(CCC(=O)N)C(CF)O | O=[N+:7]([O-])[CH:6]([CH2:5][CH2:4][C:2]([NH2:1])=[O:3])[CH:8]([OH:9])[CH2:10][F:11]>>[NH2:1][C:2](=[O:3])[CH2:4][CH2:5][CH:6]([NH2:7])[CH:8]([OH:9])[CH2:10][F:11] | NC(=O)CCC(C(O)CF)[N+](=O)[O-] | NC(=O)CCC(N)C(O)CF | null | [Ni] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | null | O=[N+;H0;D3:1](-[O-])-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[C:4])-[NH2;D1;+0:1] | null | [] | null | null | 6 | HOUR | To a solution of 6-fluoro-5-hydroxy-4-nitro-hexanoic acid amide (0.5 g, 2.58 mmol) in MeOH (20 mL) was added Raney Ni (about 200 mg), and the mixture was shaken under H2 (40-45 psi) at room temperature for 6 h. It was filtered and the catalyst was washed with MeOH (3×10 mL). The MeOH solution was evaporated and the res... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | null | Other | [Ni].CO | null | 6 | NC(=O)CCC(C(O)CF)[N+](=O)[O-]>[Ni].CO>NC(=O)CCC(N)C(O)CF |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd198af0bccc46ceba3df9a587ad8e88 | CN.COC(=O)CCC[N+](=O)[O-]>>CNC(=O)CCC[N+](=O)[O-] | [N+](=O)([O-])CCCC(=O)OC.CN>>CNC(CCC[N+](=O)[O-])=O | [CH3:1][NH2:2].CO[C:3](=[O:4])[CH2:5][CH2:6][CH2:7][N+:8](=[O:9])[O-:10]>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][N+:8](=[O:9])[O-:10] | CN.COC(=O)CCC[N+](=O)[O-] | CNC(=O)CCC[N+](=O)[O-] | null | null | null | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[NH2;D1;+0:6]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:6]-[C;D1;H3:5] | 98 | [{"value": 98.0, "product": "CNC(CCC[N+](=O)[O-])=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.6, "product": "CNC(CCC[N+](=O)[O-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | To a sealed reaction vessel was added methyl 4-nitrobutyrate (1.00 g, 6.80 mmol) and methylamine (2.0 M methylamine in MeOH, 50.0 mL, 100 mmol). The resulting yellow solution was stirred at room temperature for 20 h. The solvent was evaporated and the residue was purified by flash chromatography (silica gel, load: CH2C... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | null | HO- | null | null | 20 | CN.COC(=O)CCC[N+](=O)[O-]>>CNC(=O)CCC[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36430919cd3a43ee861a6cbe16004a7b | CNC(=O)CCC[N+](=O)[O-].OCCF>>CNC(=O)CCC(C(O)CF)[N+](=O)[O-] | CCN(CC)CC.CNC(CCC[N+](=O)[O-])=O.C(C(=O)Cl)(=O)Cl.CS(=O)C.FCCO>>CNC(CCC(C(CF)O)[N+](=O)[O-])=O | [CH3:1][NH:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][N+:12](=[O:13])[O-:14].[CH2:8]([OH:9])[CH2:10][F:11]>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][CH2:6][CH:7]([CH:8]([OH:9])[CH2:10][F:11])[N+:12](=[O:13])[O-:14] | CNC(=O)CCC[N+](=O)[O-].OCCF | CNC(=O)CCC(C(O)CF)[N+](=O)[O-] | null | null | ClCCl | C-C Coupling | OtherReaction | a76739cb57e2584c86ca56ae2e25a18c069d633832049c5e8d43eaf1c7ff6072 | 9fa23f1768d037fcd2a30655674d1b20d68d9c34d67b82adb67ad3f0e3eeac7e | null | [#7:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[CH2;D2;+0:6]-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9].[F;D1;H0:10]-[C:11]-[CH2;D2;+0:12]-[O;D1;H1:13]>>[#7:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[CH;D3;+0:6](-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9])-[CH;D3;+0:12](-[O;D1;H1:13])-[C:11]-[F;D1;H0:10] | 40 | [{"value": 40.0, "product": "CNC(CCC(C(CF)O)[N+](=O)[O-])=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.0, "product": "CNC(CCC(C(CF)O)[N+](=O)[O-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | To a clear solution of oxalyl chloride (2.0 M oxalyl chloride in dichloromethane, 0.868 g, 6.84 mmol) at −74° C. was added anhydrous DMSO (1.06 mL, 14.9 mmol) dropwise over 10 minutes while maintaining the internal temperature <−60° C. The white suspension was stirred for 15 min, then 2-fluoroethanol (0.273 mL, 4.65 mm... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary alcohol | Nitro group.Secondary alcohol | null | null | null | null | ClCCl | 0 | 0.25 | CNC(=O)CCC[N+](=O)[O-].OCCF>ClCCl>CNC(=O)CCC(C(O)CF)[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0b7d8e7f59b64f14b2c09fbad273ee7f | CNC(=O)CCC(C(O)CF)[N+](=O)[O-]>>CNC(=O)CCC(N)C(O)CF | CNC(CCC(C(CF)O)[N+](=O)[O-])=O>>CNC(CCC(C(CF)O)N)=O | O=[N+:8]([O-])[CH:7]([CH2:6][CH2:5][C:3]([NH:2][CH3:1])=[O:4])[CH:9]([OH:10])[CH2:11][F:12]>>[CH3:1][NH:2][C:3](=[O:4])[CH2:5][CH2:6][CH:7]([NH2:8])[CH:9]([OH:10])[CH2:11][F:12] | CNC(=O)CCC(C(O)CF)[N+](=O)[O-] | CNC(=O)CCC(N)C(O)CF | null | [Ni] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | null | O=[N+;H0;D3:1](-[O-])-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[C:4])-[NH2;D1;+0:1] | 90 | [{"value": 90.0, "product": "CNC(CCC(C(CF)O)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.9, "product": "CNC(CCC(C(CF)O)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of 6-fluoro-5-hydroxy-4-nitro-hexanoic acid methylamide (0.325 g, 1.56 mmol) in MeOH (12 mL) was added Raney Ni (about 0.12 g), and the mixture was shaken under H2 (40-45 psi) at room temperature for 18 h. The black mixture was filtered through celite, and the celite was washed with additional MeOH (100 m... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | null | Other | [Ni].CO | null | 18 | CNC(=O)CCC(C(O)CF)[N+](=O)[O-]>[Ni].CO>CNC(=O)CCC(N)C(O)CF |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b24b3951135941398bb6b1c74b84edca | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)NC(CC(=O)O)C(=O)CF.CNC>>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)NC(CC(=O)N(C)C)C(=O)CF | C(=O)(OCC1=CC=CC=C1)N[C@@H](C(C)C)C(=O)NC(CC(=O)O)C(CF)=O.CNC.CCN=C=NCCCN(C)C.C=1C=CC2=C(C1)N=NN2O>>CN(C(CC(C(CF)=O)NC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)=O)C | O[C:21]([CH2:20][CH:19]([NH:18][C:16]([C@H:4]([CH:2]([CH3:1])[CH3:3])[NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17])[C:26](=[O:27])[CH2:28][F:29])=[O:22].[NH:23]([CH3:24])[CH3:25]>>[CH3:1][CH:2]([CH3:3])[C@H:4]([NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]... | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)NC(CC(=O)O)C(=O)CF.CNC | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)NC(CC(=O)N(C)C)C(=O)CF | null | null | C(C)(=O)OCC.C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]=[O;D1;H0:6].[C;D1;H3:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C;D1;H3:7]-[N;H0;D3;+0:8](-[C;D1;H3:9])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5]=[O;D1;H0:6] | 6 | [{"value": 6.0, "product": "CN(C(CC(C(CF)=O)NC([C@@H](NC(=O)OCC1=CC=CC=C1)C(C)C)=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | To a solution of 3-(CBz-Val-amido)-5-fluoro-4-oxo-pentanoic acid (150 mg, 0.39 mmol) in THF (5 ml) was added a solution of 2.0 M dimethylamine in THF (0.2 ml, 0.4 mmol), EDCI (82.2 mg, 0.42 mmol) and HOBT (106 mg, 0.78 mmol) at 0° C. The resulting mixture was stirred for 2 h at 0° C., then was stirred at room temperatu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HO- | C(C)(=O)OCC.C1CCOC1 | 0 | 2 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)NC(CC(=O)O)C(=O)CF.CNC>C(C)(=O)OCC.C1CCOC1>CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)NC(CC(=O)N(C)C)C(=O)CF |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d9377c9ba184aa9b5aa36b9512eb16a | CNC.COC(=O)CCC[N+](=O)[O-]>>CN(C)C(=O)CCC[N+](=O)[O-] | [N+](=O)([O-])CCCC(=O)OC.O.CNC>>CN(C(CCC[N+](=O)[O-])=O)C | [CH3:1][NH:2][CH3:3].CO[C:4](=[O:5])[CH2:6][CH2:7][CH2:8][N+:9](=[O:10])[O-:11]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][CH2:7][CH2:8][N+:9](=[O:10])[O-:11] | CNC.COC(=O)CCC[N+](=O)[O-] | CN(C)C(=O)CCC[N+](=O)[O-] | null | null | CO | Acylation | Aminolysis of esters | d147787750807073759132276086de98566af6772417f9288b6300bf1de7801c | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | null | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C;D1;H3:5]-[NH;D2;+0:6]-[C;D1;H3:7]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:6](-[C;D1;H3:5])-[C;D1;H3:7] | 91 | [{"value": 91.0, "product": "CN(C(CCC[N+](=O)[O-])=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.9, "product": "CN(C(CCC[N+](=O)[O-])=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | To a solution of methyl 4-nitrobutyrate (1.0 g, 6.80 mmol) in methanol (10 ml) was added 40% dimethylamine water solution (12.5 ml, 102 mmol). The solution was stirred at room temperature for 48 h, concentrated by vacuum, and diluted with ethyl acetate (20 ml). The organic layer was dried and evaporated. The residue wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | null | null | HO- | CO | null | 48 | CNC.COC(=O)CCC[N+](=O)[O-]>CO>CN(C)C(=O)CCC[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0cc54313531741cf942a5ec76f15dffe | CN(C)C(=O)CCC[N+](=O)[O-].OCCF>>CN(C)C(=O)CCC(C(O)CF)[N+](=O)[O-] | CCN(CC)CC.CN(C(CCC[N+](=O)[O-])=O)C.C(C(=O)Cl)(=O)Cl.CS(=O)C.FCCO>>CN(C(CCC(C(CF)O)[N+](=O)[O-])=O)C | [CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][CH2:7][CH2:8][N+:13](=[O:14])[O-:15].[CH2:9]([OH:10])[CH2:11][F:12]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][CH2:7][CH:8]([CH:9]([OH:10])[CH2:11][F:12])[N+:13](=[O:14])[O-:15] | CN(C)C(=O)CCC[N+](=O)[O-].OCCF | CN(C)C(=O)CCC(C(O)CF)[N+](=O)[O-] | null | null | ClCCl.C(Cl)Cl | C-C Coupling | OtherReaction | a76739cb57e2584c86ca56ae2e25a18c069d633832049c5e8d43eaf1c7ff6072 | 9fa23f1768d037fcd2a30655674d1b20d68d9c34d67b82adb67ad3f0e3eeac7e | null | [#7:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[CH2;D2;+0:6]-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9].[F;D1;H0:10]-[C:11]-[CH2;D2;+0:12]-[O;D1;H1:13]>>[#7:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[CH;D3;+0:6](-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9])-[CH;D3;+0:12](-[O;D1;H1:13])-[C:11]-[F;D1;H0:10] | 89 | [{"value": 89.0, "product": "CN(C(CCC(C(CF)O)[N+](=O)[O-])=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.6, "product": "CN(C(CCC(C(CF)O)[N+](=O)[O-])=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 15 | MINUTE | To a cooled (−78° C.) solution of oxalyl chloride (0.9 ml, 9.63 mmol) in anhydrous dichloromethane (5 ml) was added anhydrous DMSO (1.4 ml, 19.38 mmol) dropwise and the reaction mixture was stirred for 15 min. A solution of 2-fluoroethanol (0.44 mL, 7.5 mmol) in dichloromethane (2 ml) was slowly added into the reaction... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Primary alcohol | Nitro group.Secondary alcohol | null | null | null | null | ClCCl.C(Cl)Cl | 0 | 0.25 | CN(C)C(=O)CCC[N+](=O)[O-].OCCF>ClCCl.C(Cl)Cl>CN(C)C(=O)CCC(C(O)CF)[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96b8dad7630b44038b0ed037edf7fea9 | CN(C)C(=O)CCC(C(O)CF)[N+](=O)[O-]>>CN(C)C(=O)CCC(N)C(O)CF | CN(C(CCC(C(CF)O)[N+](=O)[O-])=O)C>>CN(C(CCC(C(CF)O)N)=O)C | O=[N+:9]([O-])[CH:8]([CH2:7][CH2:6][C:4]([N:2]([CH3:1])[CH3:3])=[O:5])[CH:10]([OH:11])[CH2:12][F:13]>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[CH2:6][CH2:7][CH:8]([NH2:9])[CH:10]([OH:11])[CH2:12][F:13] | CN(C)C(=O)CCC(C(O)CF)[N+](=O)[O-] | CN(C)C(=O)CCC(N)C(O)CF | null | [Ni] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | null | O=[N+;H0;D3:1](-[O-])-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[C:4])-[NH2;D1;+0:1] | 87 | [{"value": 87.0, "product": "CN(C(CCC(C(CF)O)N)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.0, "product": "CN(C(CCC(C(CF)O)N)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a solution of 6-fluoro-5-hydroxy-4-nitro-hexanoic acid dimethylamide (1.22 g, 5.5 mmol) in MeOH (20 mL) was added Ranny Ni (about 500 mg), and the mixture was hydrogenated under 40-45 psi H2 at room temperature for 6 h. The catalyst was removed. The MeOH solution was evaporated and the residue oil (0.92 g, yield 87%... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | null | Other | [Ni].CO | null | 6 | CN(C)C(=O)CCC(C(O)CF)[N+](=O)[O-]>[Ni].CO>CN(C)C(=O)CCC(N)C(O)CF |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d0ce27d6184f4135ae882c06d881c0a7 | O=C(O)c1cc(F)ccc1F.OC[C@H]1CCCN1>>O=C1c2cc(F)ccc2OC[C@H]2CCCN12 | [H-].[Na+].N1[C@H](CCC1)CO.FC1=C(C(=O)O)C=C(C=C1)F.C(=O)(N1C=NC=C1)N1C=NC=C1>>FC=1C=CC2=C(C(N3[C@@H](CO2)CCC3)=O)C1 | O[C:2](=[O:1])[c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1F.[OH:10][CH2:11][C@H:12]1[CH2:13][CH2:14][CH2:15][NH:16]1>>[O:1]=[C:2]1[c:3]2[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]2[O:10][CH2:11][C@H:12]2[CH2:13][CH2:14][CH2:15][N:16]12 | O=C(O)c1cc(F)ccc1F.OC[C@H]1CCCN1 | O=C1c2cc(F)ccc2OC[C@H]2CCCN12 | null | null | O.CN(C=O)C | Acylation | OtherReaction | 23bfe36333c10b78bd895c9451d67eefa4d1ac93dd42c9962d3361f874547a01 | 674260e6f21078d04350bbd52c1d1179d0c4074cbda516a19d557550f844f0ae | O=C1c2ccccc2OC[C@H]2CCCN12 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;H0;D3;+0:5](-O)=[O;D1;H0:6]):[c:7].[OH;D1;+0:8]-[C:9]-[C:10]1-[C:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[O;D1;H0:6]=[C;H0;D3;+0:5]1-[N;H0;D3;+0:14]2-[C:13]-[C:12]-[C:11]-[C:10]-2-[C:9]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]-1:[c:7] | 20.7 | [{"value": 20.7, "product": "FC=1C=CC2=C(C(N3[C@@H](CO2)CCC3)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2,5-difluorobenzoic acid (1.0 g; 6.325 mmol) in dimethylformamide (5 ml) was added 1,1′- carbonyldiimidazole (1.07 g; 6.64 mmol) and the solution stirred at room temperature for 1 h, followed by the addition of (R)-(−)-2-pyrrolidinemethanol (0.655 ml; 6.64 mmol). The reaction was stirred at room temper... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Primary alcohol.Secondary amine | Ether.Tertiary amide | c1ccccc1.C1CCNC1 | c1ccc2c(c1)CN1CCC[C@@H]1CO2 | c1ccc2c(c1)CN1CCC[C@@H]1CO2 | HF | O.CN(C=O)C | null | 1 | O=C(O)c1cc(F)ccc1F.OC[C@H]1CCCN1>O.CN(C=O)C>O=C1c2cc(F)ccc2OC[C@H]2CCCN12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7b425ad4d0054155806e5ccec0c6959c | O=C(Cl)c1cccc(Cl)c1F.OC[C@@H]1CCCN1>>O=C1c2cccc(Cl)c2OC[C@@H]2CCCN12 | C([O-])([O-])=O.[Cs+].[Cs+].ClC=1C(=C(C(=O)Cl)C=CC1)F.C(C)N(CC)CC.N1[C@@H](CCC1)CO>>ClC1=CC=CC=2C(N3[C@H](COC21)CCC3)=O | F[c:9]1[c:3]([C:2](Cl)=[O:1])[cH:4][cH:5][cH:6][c:7]1[Cl:8].[OH:10][CH2:11][C@@H:12]1[CH2:13][CH2:14][CH2:15][NH:16]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][c:7]([Cl:8])[c:9]2[O:10][CH2:11][C@@H:12]2[CH2:13][CH2:14][CH2:15][N:16]12 | O=C(Cl)c1cccc(Cl)c1F.OC[C@@H]1CCCN1 | O=C1c2cccc(Cl)c2OC[C@@H]2CCCN12 | null | null | O.CN(C=O)C | Acylation | OtherReaction | d7d785c5624ce826bd862e5b93570242be063be05747ca8fa1114a94351c3c6c | 6a6f4232184d0953b8cf75ef77862f7dc127a9ba2c08f4d8f3fd27d554ef6487 | O=C1c2ccccc2OC[C@@H]2CCCN12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c;H0;D3;+0:5](-F):[c:6](-[Cl;D1;H0:7]):[c:8].[OH;D1;+0:9]-[C:10]-[C:11]1-[C:12]-[C:13]-[C:14]-[NH;D2;+0:15]-1>>[Cl;D1;H0:7]-[c:6](:[c:8]):[c;H0;D3;+0:5]1:[c:3](:[c:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[C:12]-[C:11]-2-[C:10]-[O;H0;D2;+0:9]-1 | null | [] | 120 | CELSIUS | 1 | HOUR | To a solution of 3-chloro-2-fluorobenzoyl chloride (2.2 g; 11.4 mmol) in dimethylformamide (5 ml) was added triethylamine (1.7 mL; 11.7 mmol) and (S)-(+)-2-pyrrolidinemethanol (1.13 mL; 11.4 mmol). The mixture was stirred for 1 h then caesium carbonate (7.4 g; 22.7 mmol) was added and the reaction heated at 120° C. for... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide.Primary alcohol.Secondary amine | Ether.Tertiary amide | c1ccccc1.C1CCNC1 | c1ccc2c(c1)CN1CCC[C@H]1CO2 | c1ccc2c(c1)CN1CCC[C@H]1CO2 | HF | O.CN(C=O)C | 120 | 1 | O=C(Cl)c1cccc(Cl)c1F.OC[C@@H]1CCCN1>O.CN(C=O)C>O=C1c2cccc(Cl)c2OC[C@@H]2CCCN12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d66209a5de7c4b3787d8e73fb433a254 | C[O-].O=C1c2ccc(F)cc2OC[C@@H]2CCCN12>>COc1ccc2c(c1)OC[C@@H]1CCCN1C2=O | FC1=CC2=C(C(N3[C@H](CO2)CCC3)=O)C=C1.C[O-].[Na+]>>COC1=CC2=C(C(N3[C@H](CO2)CCC3)=O)C=C1 | [CH3:1][O-:2].F[c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[O:9][CH2:10][C@@H:11]1[CH2:12][CH2:13][CH2:14][N:15]1[C:16]2=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[O:9][CH2:10][C@@H:11]1[CH2:12][CH2:13][CH2:14][N:15]1[C:16]2=[O:17] | C[O-].O=C1c2ccc(F)cc2OC[C@@H]2CCCN12 | COc1ccc2c(c1)OC[C@@H]1CCCN1C2=O | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | a62a240686a795102d234d30bf6dad9bed77538a873e10e6cc2d9d68a2e1222d | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | O=C1c2ccccc2OC[C@@H]2CCCN12 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[#8:6].[C;D1;H3:7]-[O-;H0;D1:8]>>[#8:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[O;H0;D2;+0:8]-[C;D1;H3:7]):[c:2]:[c:3] | null | [] | 110 | CELSIUS | null | null | A solution of (S)-8-fluoro-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]-benzoxazepine-5-one (0.5 g; 2.14 mmol), prepared as described in Example 5A, and sodium methoxide (0.244 g; 4.52 mmol) in dimethylformamide (2 mL) was heated at 110° C. for 3 h. The reaction was diluted with water and extracted with ethyl acetat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccc2c(c1)CN1CCC[C@H]1CO2 | c1ccc2c(c1)CN1CCC[C@H]1CO2 | c1ccc2c(c1)CN1CCC[C@H]1CO2 | Other | O.CN(C=O)C | 110 | null | C[O-].O=C1c2ccc(F)cc2OC[C@@H]2CCCN12>O.CN(C=O)C>COc1ccc2c(c1)OC[C@@H]1CCCN1C2=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9e4e3e7114bc4854bd74b57e4f8595b1 | O=C1c2cc([N+](=O)[O-])ccc2OC[C@@H]2CCCN12>>Nc1ccc2c(c1)C(=O)N1CCC[C@H]1CO2 | [H][H].[N+](=O)([O-])C=1C=CC2=C(C(N3[C@H](CO2)CCC3)=O)C1.CO.[H][H]>>NC=1C=CC2=C(C(N3[C@H](CO2)CCC3)=O)C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[N:10]1[CH2:11][CH2:12][CH2:13][C@H:14]1[CH2:15][O:16]2>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[N:10]1[CH2:11][CH2:12][CH2:13][C@H:14]1[CH2:15][O:16]2 | O=C1c2cc([N+](=O)[O-])ccc2OC[C@@H]2CCCN12 | Nc1ccc2c(c1)C(=O)N1CCC[C@H]1CO2 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C1c2ccccc2OC[C@@H]2CCCN12 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 93.8 | [{"value": 93.8, "product": "NC=1C=CC2=C(C(N3[C@H](CO2)CCC3)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (S)-7-nitro-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]benzoxazepine-5-one (7.4 g), prepared as described in Example 3L, in ethanol (100 ml) and methanol (50 ml) was hydrogenated over 10% palladium on activated carbon under 2 bar hydrogen, until the uptake of hydrogen ceased. The mixture was filtered ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c(c1)CN1CCC[C@H]1CO2 | Other | [Pd].C(C)O | null | null | O=C1c2cc([N+](=O)[O-])ccc2OC[C@@H]2CCCN12>[Pd].C(C)O>Nc1ccc2c(c1)C(=O)N1CCC[C@H]1CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c8dbc932f36e4d468cc1d5184fcf87ba | CO.CS(C)=O.O=C1c2cc(Br)ccc2OC[C@@H]2CCCN12>>COC(=O)c1ccc2c(c1)C(=O)N1CCC[C@H]1CO2 | O.BrC=1C=CC2=C(C(N3[C@H](CO2)CCC3)=O)C1.CS(=O)C.C(C)N(CC)CC.CO>>C1CCN2[C@@H]1COC1=C(C2=O)C=C(C=C1)C(=O)OC | [CH3:1][OH:2].CS([CH3:3])=[O:4].Br[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11](=[O:12])[N:13]1[CH2:14][CH2:15][CH2:16][C@H:17]1[CH2:18][O:19]2>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[C:11](=[O:12])[N:13]1[CH2:14][CH2:15][CH2:16][C@H:17]1[CH2:18][O:19]2 | CO.CS(C)=O.O=C1c2cc(Br)ccc2OC[C@@H]2CCCN12 | COC(=O)c1ccc2c(c1)C(=O)N1CCC[C@H]1CO2 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 | null | Acylation | OtherReaction | 6cad2ea6287f11390421ca4725be2b428e8744bc4e6d97f84d1c65bb69b87673 | 16b52b877a927c213406a54b560a524723fe0fec6d136fd2e421a2bc59608f75 | O=C1c2ccccc2OC[C@@H]2CCCN12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](=[O;D1;H0:5])-[#7:6]):[c:7]:[c:8].C-S(-[CH3;D1;+0:9])=[O;H0;D1;+0:10].[C;D1;H3:11]-[OH;D1;+0:12]>>[#7:6]-[C:4](=[O;D1;H0:5])-[c:3]:[c:2]:[c;H0;D3;+0:1](-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[O;H0;D2;+0:12]-[C;D1;H3:11]):[c:7]:[c:8] | null | [] | 100 | CELSIUS | null | null | To a solution of (S)-7-Bromo-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]-benzoxazepine-5-one (5 g; 17.76 mmol), prepared as described in Example 3J, in dimethylsulfoxide (80 ml) was added palladium acetate (225 mg; 1 mmol), 1,3-bis-(diphenylphosphino)propane (413 mg; 1 mmol), triethylamine (5 ml; 36 mmol) and metha... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Sulfoxide.Methanol | Ester | c1ccc2c(c1)CN1CCC[C@H]1CO2 | c1ccc2c(c1)CN1CCC[C@H]1CO2 | c1ccc2c(c1)CN1CCC[C@H]1CO2 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 | 100 | null | CO.CS(C)=O.O=C1c2cc(Br)ccc2OC[C@@H]2CCCN12>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1.C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P(CCCP(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1>COC(=O)c1ccc2c(c1)C(=O)N1CCC[C@H]1CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-03bf3c73c5fb450a8bfebccbbc413983 | O=C(O)c1ccc2c(c1)C(=O)N1CCC[C@H]1CO2.O=S(Cl)Cl>>O=C(Cl)c1ccc2c(c1)C(=O)N1CCC[C@H]1CO2 | C1CCN2[C@@H]1COC1=C(C2=O)C=C(C=C1)C(=O)O.S(=O)(Cl)Cl>>C1CCN2[C@@H]1COC1=C(C2=O)C=C(C=C1)C(=O)Cl | O[C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][CH2:15][C@H:16]1[CH2:17][O:18]2.O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][CH2:15][C@H:16]1[CH2:17][O:18]2 | O=C(O)c1ccc2c(c1)C(=O)N1CCC[C@H]1CO2.O=S(Cl)Cl | O=C(Cl)c1ccc2c(c1)C(=O)N1CCC[C@H]1CO2 | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | O=C1c2ccccc2OC[C@@H]2CCCN12 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A solution of the above carboxylic acid derivative (2.38 g; 9.64 mmol) in thionyl chloride (10 ml) was heated under reflux for 1.5 h. The excess thionyl chloride was evaporated under reduced pressure to giving (S)-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]benzoxazepine-5-one-7-carboxylic acid chloride (2.56 g) as ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccc2c(c1)CN1CCC[C@H]1CO2 | HCl | null | null | null | O=C(O)c1ccc2c(c1)C(=O)N1CCC[C@H]1CO2.O=S(Cl)Cl>>O=C(Cl)c1ccc2c(c1)C(=O)N1CCC[C@H]1CO2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6cefee6797af4be89e1c69eee56f99c0 | O=C(O)c1ccccc1Cl.OC[C@@H]1CCCN1>>O=C(c1ccccc1Cl)N1CCC[C@H]1CO | N1[C@@H](CCC1)CO.ClC1=C(C(=O)O)C=CC=C1.C(=O)(N1C=NC=C1)N1C=NC=C1>>ClC1=C(C(=O)N2[C@@H](CCC2)CO)C=CC=C1 | O[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[Cl:9].[NH:10]1[CH2:11][CH2:12][CH2:13][C@H:14]1[CH2:15][OH:16]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[Cl:9])[N:10]1[CH2:11][CH2:12][CH2:13][C@H:14]1[CH2:15][OH:16] | O=C(O)c1ccccc1Cl.OC[C@@H]1CCCN1 | O=C(c1ccccc1Cl)N1CCC[C@H]1CO | null | null | CN(C=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | a590d96426a2fbaed42913d9daf8a16471a16de4978200f1d35a30a10009ebe7 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccccc1)N1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[C:6]-[C:7]1-[C:8]-[C:9]-[C:10]-[N;H0;D3;+0:11]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 66.6 | [{"value": 66.6, "product": "ClC1=C(C(=O)N2[C@@H](CCC2)CO)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To 2-chlorobenzoic acid (10 g; 63.9 mmol) in dimethylformamide (100 ml) under nitrogen was added carbonyldiimidazole (10.9 g; 67.1 mmol) and the solution stirred for 1 h at room temperature. (S)-(+)-2-pyrrolidinemethanol (7.56 ml, 76.6 mmol) was added and the mixture stirred at 40° C. for 18 h. The solvent was removed ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1 | HO- | CN(C=O)C | null | 1 | O=C(O)c1ccccc1Cl.OC[C@@H]1CCCN1>CN(C=O)C>O=C(c1ccccc1Cl)N1CCC[C@H]1CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-489ae4dc7feb4b79a81ff94f15195529 | O=C(c1ccccc1Cl)N1CCCC1CO>>CCC(O)[C@@H]1CCCN1C(=O)c1ccccc1Cl | C(C(=O)Cl)(=O)Cl.C(C)[Mg]Br.C(C)N(CC)CC.[Cl-].[NH4+].CS(=O)C.ClC1=C(C(=O)N2C(CCC2)CO)C=CC=C1>>ClC1=C(C(=O)N2[C@@H](CCC2)C(O)CC)C=CC=C1 | [CH2:3]([OH:4])[CH:5]1[CH2:6][CH2:7][CH2:8][N:9]1[C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[Cl:18]>>[CH3:1][CH2:2][CH:3]([OH:4])[C@@H:5]1[CH2:6][CH2:7][CH2:8][N:9]1[C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][c:17]1[Cl:18] | O=C(c1ccccc1Cl)N1CCCC1CO | CCC(O)[C@@H]1CCCN1C(=O)c1ccccc1Cl | null | null | O1CCCC1.C(C)O | Miscellaneous | OtherReaction | e1c73a3df7824bf651f4a0199a6c43c1af6351611188148386201ef6827ab78e | d31744c89f64d42a254255c6eb9d3a9e3c96fd70790b6d54cedb213f87ec2869 | O=C(c1ccccc1)N1CCCC1 | [O;D1;H0:1]=[C:2](-[c:3])-[#7:4]1-[C:5]-[C:6]-[C:7]-[CH;D3;+0:8]-1-[CH2;D2;+0:9]-[O;D1;H1:10]>>[C;D1;H3:11]-[C:12]-[CH;D3;+0:9](-[O;D1;H1:10])-[C@@H;D3;+0:8]1-[C:7]-[C:6]-[C:5]-[#7:4]-1-[C:2](=[O;D1;H0:1])-[c:3] | null | [] | 0 | CELSIUS | 15 | MINUTE | Tetrahydrofuran (24 ml) was cooled to −60° C. with stirring and oxalyl chloride (1.15 ml, 13.2 mmol) was added. Dimethylsulfoxide (0.98 ml, 13.8 mmol) was then added dropwise. The mixture was stirred for 20 minutes, then a solution of 1-(2-chlorobenzoyl)-2-pyrrolidinemethanol (3.0 g, 12.5 mmol) in tetrahydrofuran (24 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Secondary alcohol | null | null | C1CC[NH]C1.c1ccccc1 | Other | O1CCCC1.C(C)O | 0 | 0.25 | O=C(c1ccccc1Cl)N1CCCC1CO>O1CCCC1.C(C)O>CCC(O)[C@@H]1CCCN1C(=O)c1ccccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-26ae3fa05b0f47b48f9ceb895579711b | CCO.O=C(O)C1COCCN1>>CCOC(=O)C1COCCN1 | N1C(COCC1)C(=O)O.Cl.C(C)O>>N1C(COCC1)C(=O)OCC | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[CH:6]1[CH2:7][O:8][CH2:9][CH2:10][NH:11]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][O:8][CH2:9][CH2:10][NH:11]1 | CCO.O=C(O)C1COCCN1 | CCOC(=O)C1COCCN1 | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | C1COCCN1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#7:4]-[C:5])-[C:6]-[#8:7].[C;D1;H3:8]-[C:9]-[OH;D1;+0:10]>>[#8:7]-[C:6]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:10]-[C:9]-[C;D1;H3:8])-[#7:4]-[C:5] | null | [] | null | null | null | null | A solution of morpholine-3-carboxylic acid (4.035 g; 30.8 mmol) in ethanol (250 ml) was saturated with gaseous HCl, then stirred for a week. The solvent was evaporated and the residue taken up in water and made basic (pH ˜10) with sodium hydrogen carbonate and sodium carbonate. The mixture was then extracted with dichl... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | C1COCCN1 | HO- | null | null | null | CCO.O=C(O)C1COCCN1>>CCOC(=O)C1COCCN1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f6900f7a80e49c0abab2c878ff8e88b | O=C(Cl)c1ccccc1F.OCC1COCCN1>>O=C(c1ccccc1F)N1CCOCC1CO | [OH-].[Na+].OCC1NCCOC1.FC1=C(C(=O)Cl)C=CC=C1.C(C)N(CC)CC>>FC1=C(C(=O)N2C(COCC2)CO)C=CC=C1 | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[F:9].[NH:10]1[CH2:11][CH2:12][O:13][CH2:14][CH:15]1[CH2:16][OH:17]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[F:9])[N:10]1[CH2:11][CH2:12][O:13][CH2:14][CH:15]1[CH2:16][OH:17] | O=C(Cl)c1ccccc1F.OCC1COCCN1 | O=C(c1ccccc1F)N1CCOCC1CO | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | b2821ffedb27fdb32ee8909e6c37f5667f3a9287b29ba6c49c7967ceba44bfc3 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCOCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]1-[C:8]-[#8:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[C:6]-[C:7]1-[C:8]-[#8:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 23.4 | [{"value": 23.4, "product": "FC1=C(C(=O)N2C(COCC2)CO)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | To a solution of 3-(hydroxymethyl)morpholine (345 mg; 2.95 mmol) in dichloromethane (10 mL) was carefully added 2-fluorobenzoyl chloride (0.35 mL; 2.95 mmol) and triethylamine (0.62 mL; 4.42 mmol) and the reaction stirred for 0.5 h. The product was combined with 4 N NaOH (10 mL) to hydrolyse any ester and the organic l... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HCl | ClCCl | null | 0.5 | O=C(Cl)c1ccccc1F.OCC1COCCN1>ClCCl>O=C(c1ccccc1F)N1CCOCC1CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-86478f69b3b9453ab3de7d762b3d1c20 | CC(C)(C)OC(=O)N1CC[C@H]1CO>>OC[C@@H]1CCN1 | FC(C(=O)O)(F)F.C(C)(C)(C)OC(=O)N1[C@@H](CC1)CO>>FC(C(=O)O)(F)F.OC[C@H]1NCC1 | CC(C)(C)OC(=O)[N:13]1[C@H:10]([CH2:9][OH:8])[CH2:11][CH2:12]1>>[OH:8][CH2:9][C@@H:10]1[CH2:11][CH2:12][NH:13]1 | CC(C)(C)OC(=O)N1CC[C@H]1CO | OC[C@@H]1CCN1 | null | null | ClCCl | Reduction | Boc amine deprotection | 343286afc91dc16da2aad3490e802fd6b05a55674e1c7133ca7403ccd8e157ce | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | C1CNC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-1-[C:5]>>[C:5]-[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-1 | null | [] | 5 | CELSIUS | 18 | HOUR | Trifluoroacetic acid (5 ml) in dichloromethane (5 ml) was added to a stirred solution of (S)-N-tert-butoxycarbonyl-azetidin-2-ylmethanol (1.17 g, 6.25 mmol) in dichloromethane (8 ml) cooled to [5° C. under nitrogen. The reaction was stirred for 18 h with the temperature being allowed to rise slowly to RT. Solvent and e... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]C1 | C1CNC1 | C1CNC1 | HO- | ClCCl | 5 | 18 | CC(C)(C)OC(=O)N1CC[C@H]1CO>ClCCl>OC[C@@H]1CCN1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-26ef0bf8cefc43b28d81bcb0c136216e | O=C(Cl)c1ccccc1F.OC[C@@H]1CCN1>>O=C(c1ccccc1F)N1CC[C@H]1CO | O.C(C)N(CC)CC.FC(C(=O)O)(F)F.OC[C@H]1NCC1.FC1=C(C(=O)Cl)C=CC=C1>>FC1=C(C(=O)N2[C@@H](CC2)CO)C=CC=C1 | Cl[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[F:9].[NH:10]1[CH2:11][CH2:12][C@H:13]1[CH2:14][OH:15]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[F:9])[N:10]1[CH2:11][CH2:12][C@H:13]1[CH2:14][OH:15] | O=C(Cl)c1ccccc1F.OC[C@@H]1CCN1 | O=C(c1ccccc1F)N1CC[C@H]1CO | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | 97f50c50ea213cab4f62229ae029fca8cc0b30f15ba697a1ed4256ce0d0240f9 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[C:6]-[C:7]1-[C:8]-[C:9]-[N;H0;D3;+0:10]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 76.6 | [{"value": 76.6, "product": "FC1=C(C(=O)N2[C@@H](CC2)CO)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 18 | HOUR | Trifluoroacetic acid (5 ml) in dichloromethane (5 ml) was added to a stirred solution of (S)-N-tert-butoxycarbonyl-azetidin-2-ylmethanol (1.17 g, 6.25 mmol) in dichloromethane (8 ml) cooled to [5° C. under nitrogen. The reaction was stirred for 18 h with the temperature being allowed to rise slowly to RT. Solvent and e... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CNC1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1 | HCl | ClCCl | 5 | 18 | O=C(Cl)c1ccccc1F.OC[C@@H]1CCN1>ClCCl>O=C(c1ccccc1F)N1CC[C@H]1CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0871c3adbfeb4857b04fd8c8a3344c03 | CC(C)(N)CO.CCOC(=O)C=O>>CCOC(=O)C=NC(C)(C)CO | NC(CO)(C)C.C(C=O)(=O)OCC>>C(C)OC(C=NC(CO)(C)C)=O | [NH2:7][C:8]([CH3:9])([CH3:10])[CH2:11][OH:12].O=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[N:7][C:8]([CH3:9])([CH3:10])[CH2:11][OH:12] | CC(C)(N)CO.CCOC(=O)C=O | CCOC(=O)C=NC(C)(C)CO | null | null | ClCCl | Heteroatom Alkylation and Arylation | Addition of primary amines to aldehydes/thiocarbonyls | c0ee46365febfce308954dbfee3ff70942c53c609273206c43bba2b5d8dea241 | bcc3f7458a973689cc4eabdb9e84f23526abfc9cab8e4d6903f65e5b3b31e41f | null | O=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].[C:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[NH2;D1;+0:10]>>[C:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[N;H0;D2;+0:10]=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5] | 98.1 | [{"value": 98.1, "product": "C(C)OC(C=NC(CO)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 2-Amino-2-methyl-1-propanol (9.54 ml, 0.10 mol) was added to a stirred solution of ethyl glyoxylate (50% soln. in toluene, 21 ml, 0.10 mol) in dichloromethane (100 ml) in the presence of 4 Å molecular sieves. The reaction was stirred under nitrogen for 16 h whereupon the system was filtered through Dicalite® and washed... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Primary amine | Ester.Substituted imine | null | null | null | HO- | ClCCl | null | 16 | CC(C)(N)CO.CCOC(=O)C=O>ClCCl>CCOC(=O)C=NC(C)(C)CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a5edd38a6cbb402091566e721fbad95c | O=C1c2ccccc2OC[C@@H]2C[C@@H](O)CN12>>O=C1C[C@H]2COc3ccccc3C(=O)N2C1 | C(C)N(CC)CC.O[C@@H]1C[C@H]2COC3=C(C(N2C1)=O)C=CC=C3.C(C(=O)Cl)(=O)Cl.CS(=O)C>>O=C1C[C@H]2COC3=C(C(N2C1)=O)C=CC=C3 | [OH:1][C@@H:2]1[CH2:3][C@H:4]2[CH2:5][O:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[C:13](=[O:14])[N:15]2[CH2:16]1>>[O:1]=[C:2]1[CH2:3][C@H:4]2[CH2:5][O:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[C:13](=[O:14])[N:15]2[CH2:16]1 | O=C1c2ccccc2OC[C@@H]2C[C@@H](O)CN12 | O=C1C[C@H]2COc3ccccc3C(=O)N2C1 | null | null | ClCCl.O.C(C)(=O)OCC | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | aadb484e791821dc7b8867fa99c19a42d42ac05786c8a1d5f1886b77a56006b3 | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C1C[C@H]2COc3ccccc3C(=O)N2C1 | [O;D1;H0:1]=[C:2]-[#7:3]1-[C:4]-[C@H;D3;+0:5](-[OH;D1;+0:6])-[C:7]-[C:8]-1>>[O;D1;H0:1]=[C:2]-[#7:3]1-[C:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[C:7]-[C:8]-1 | 22.2 | [{"value": 22.2, "product": "O=C1C[C@H]2COC3=C(C(N2C1)=O)C=CC=C3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a stirred solution of oxalyl chloride (0.52 ml; 5.94 mmol) in dry dichloromethane (15 ml) cooled to −78° C. was added a solution of dimethylsulfoxide (0.81 ml, 11.42 mmol) in dry dichloromethane (2 ml). Stirring was continued for 10 minutes followed by dropwise addition of a solution of the material (1 g) prepared i... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | c1ccc2c(c1)CN1CCC[C@H]1CO2 | c1ccc2c(c1)CN1CCC[C@H]1CO2 | c1ccc2c(c1)CN1CCC[C@H]1CO2 | null | ClCCl.O.C(C)(=O)OCC | null | 0.166667 | O=C1c2ccccc2OC[C@@H]2C[C@@H](O)CN12>ClCCl.O.C(C)(=O)OCC>O=C1C[C@H]2COc3ccccc3C(=O)N2C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f03aa728ca143b69b12629aa0cc946b | Cc1c([N+](=O)[O-])c(=O)n(C)c(=O)n1C.O=Cc1ccccc1>>Cn1c(/C=C/c2ccccc2)c([N+](=O)[O-])c(=O)n(C)c1=O | CN1C(N(C(C(=C1C)[N+](=O)[O-])=O)C)=O.C(C1=CC=CC=C1)=O.N1CCCCC1>>CN1C(N(C(C(=C1\C=C\C1=CC=CC=C1)[N+](=O)[O-])=O)C)=O | [CH3:1][n:2]1[c:3]([CH3:4])[c:12]([N+:13](=[O:14])[O-:15])[c:16](=[O:17])[n:18]([CH3:19])[c:20]1=[O:21].O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[CH3:1][n:2]1[c:3](/[CH:4]=[CH:5]/[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]([N+:13](=[O:14])[O-:15])[c:16](=[O:17])[n:18]([CH3:19])[c:20]1=[O:21] | Cc1c([N+](=O)[O-])c(=O)n(C)c(=O)n1C.O=Cc1ccccc1 | Cn1c(/C=C/c2ccccc2)c([N+](=O)[O-])c(=O)n(C)c1=O | null | null | C(C)O | C-C Coupling | OtherReaction | 43d4e2f03e758941ee99f59641d5d56e6475fe935434d251d75d5cdebbe19869 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | O=c1cc(/C=C/c2ccccc2)[nH]c(=O)[nH]1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#7;a:6]1:[c:7]:[#7;a:8]:[c:9]:[c:10]:[c:11]:1-[CH3;D1;+0:12]>>[C;D1;H3:5]-[#7;a:6]1:[c:7]:[#7;a:8]:[c:9]:[c:10]:[c:11]:1/[CH;D2;+0:12]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 60.3 | [{"value": 60.0, "product": "CN1C(N(C(C(=C1\\C=C\\C1=CC=CC=C1)[N+](=O)[O-])=O)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.3, "product": "CN1C(N(C(C(=C1\\C=C\\C1=CC=CC=C1)[N+](=O)[O-])=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1,3,6-trimethyl-5-nitro-1H-pyrimidine-2,4dione (3.00 g, 15.06 mmol), benzaldehyde (1.58 ml, 15.56 mmol), piperidine (1.41 ml, 15.56 mmol) and a 3 Å molecular sieve (6.00 g) in ethanol (70 ml) was refluxed for 4 hours, filtered and the solid was treated with a mixture of chloroform and methanol. The resulti... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | null | null | c1cncnc1.c1ccccc1 | HO- | C(C)O | null | null | Cc1c([N+](=O)[O-])c(=O)n(C)c(=O)n1C.O=Cc1ccccc1>C(C)O>Cn1c(/C=C/c2ccccc2)c([N+](=O)[O-])c(=O)n(C)c1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa884b7c18a74d53a08928ef34d5e0f1 | CC(C)(C)OC(=O)N1CCNCC1.N#CC(C#N)=C(Cl)c1ccccc1>>CC(C)(C)OC(=O)N1CCN(C(=C(C#N)C#N)c2ccccc2)CC1 | C(C)N(CC)CC.C(=O)(OC(C)(C)C)N1CCNCC1.ClC(=C(C#N)C#N)C1=CC=CC=C1>>C(#N)C(=C(C1=CC=CC=C1)N1CCN(CC1)C(=O)OC(C)(C)C)C#N | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:24][CH2:25]1.Cl[C:12](=[C:13]([C:14]#[N:15])[C:16]#[N:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([C:12](=[C:13]([C:14]#[N:15])[C:16]#[N:17])[c:18]2[cH:19][cH... | CC(C)(C)OC(=O)N1CCNCC1.N#CC(C#N)=C(Cl)c1ccccc1 | CC(C)(C)OC(=O)N1CCN(C(=C(C#N)C#N)c2ccccc2)CC1 | null | null | CCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | fb39f623f1232e56ad2a7b112e7e066b171d60d4c8c9ff76b25b5902ba1dc6db | 24343b493406f30850a2e160dec6759b529ccec020e35365ba8d762a5dbc1073 | C=C(c1ccccc1)N1CCNCC1 | Cl-[C;H0;D3;+0:1](=[C:2](-[C:3]#[N;D1;H0:4])-[C:5]#[N;D1;H0:6])-[c:7](:[c:8]):[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[N;D1;H0:4]#[C:3]-[C:2](-[C:5]#[N;D1;H0:6])=[C;H0;D3;+0:1](-[N;H0;D3;+0:13]1-[C:14]-[C:15]-[#7:10]-[C:11]-[C:12]-1)-[c:7](:[c:8]):[c:9] | null | [] | null | null | 16 | HOUR | Triethyl amine (1 ml) was added into a solution of N-Boc piperazine (1 g) and 2-(chloro(phenyl)methylene)malononitrile (1 g) in EtOH (20 ml). After 16 hours at 115° C., the reaction mixture was cooled down and some of desired product, tert-butyl 4-(2,2-dicyano-1-phenylvinyl)piperazine-1-carboxylate, precipitated out fr... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Secondary amine | Enamine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | HCl | CCO | null | 16 | CC(C)(C)OC(=O)N1CCNCC1.N#CC(C#N)=C(Cl)c1ccccc1>CCO>CC(C)(C)OC(=O)N1CCN(C(=C(C#N)C#N)c2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3281829e234c47e6b97845298d15f7f6 | CC(C)(C)OC(=O)N1CCN(C(=C(C#N)C#N)c2ccccc2)CC1>>N#CC(C#N)=C(c1ccccc1)N1CCNCC1 | C(#N)C(=C(C1=CC=CC=C1)N1CCN(CC1)C(=O)OC(C)(C)C)C#N>>C1(=CC=CC=C1)C(=C(C#N)C#N)N1CCNCC1 | CC(C)(C)OC(=O)[N:16]1[CH2:15][CH2:14][N:13]([C:6](=[C:3]([C:2]#[N:1])[C:4]#[N:5])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:18][CH2:17]1>>[N:1]#[C:2][C:3]([C:4]#[N:5])=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[N:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1 | CC(C)(C)OC(=O)N1CCN(C(=C(C#N)C#N)c2ccccc2)CC1 | N#CC(C#N)=C(c1ccccc1)N1CCNCC1 | null | null | C(Cl)Cl.C(=O)(C(F)(F)F)O | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | C=C(c1ccccc1)N1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | 71 | [{"value": 71.0, "product": "C1(=CC=CC=C1)C(=C(C#N)C#N)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | tert-Butyl 4-(2,2-dicyano-1-phenylvinyl)piperazine-1-carboxylate (2 g) was dissolved in a 33.3% solution of TFA in methylene chloride (20 ml). After 16 hour at room temperature, solvents were removed under vacuum to offer a residue which was purified using silica gel chromatography to give 2-(phenyl(piperazin-1-yl)meth... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HO- | C(Cl)Cl.C(=O)(C(F)(F)F)O | null | 16 | CC(C)(C)OC(=O)N1CCN(C(=C(C#N)C#N)c2ccccc2)CC1>C(Cl)Cl.C(=O)(C(F)(F)F)O>N#CC(C#N)=C(c1ccccc1)N1CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cdffe3ca95c74105ab1185ec0bc6e856 | CC(C)(C)OC(=O)N1CCNCC1.N#CCC(=O)c1ccccc1>>CC(C)(C)OC(=O)N1CCN(C(=CC#N)c2ccccc2)CC1 | S(=O)(=O)(C1=CC=C(C)C=C1)O.O.C(=O)(OC(C)(C)C)N1CCNCC1.O=C(CC#N)C1=CC=CC=C1>>C(#N)C=C(C1=CC=CC=C1)N1CCN(CC1)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:22][CH2:23]1.O=[C:12]([CH2:13][C:14]#[N:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([C:12](=[CH:13][C:14]#[N:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[... | CC(C)(C)OC(=O)N1CCNCC1.N#CCC(=O)c1ccccc1 | CC(C)(C)OC(=O)N1CCN(C(=CC#N)c2ccccc2)CC1 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Addition of secondary amines to ketones/thiocarbonyls | da1a6cbc7a2bb40d48a0c07dcb1e78e01be6d794c0b21a1b4a382739931e7738 | 138241c15f26b169b1f757449030b8958b9839a8f1191f1f48fa6c1d9c98427e | [CH]=C(c1ccccc1)N1CCNCC1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C:3]#[N;D1;H0:4])-[c:5](:[c:6]):[c:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[N;D1;H0:4]#[C:3]-[CH;D2;+0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[#7:8]-[C:9]-[C:10]-1)-[c:5](:[c:6]):[c:7] | null | [] | 115 | CELSIUS | null | null | TsOH—H2O (1 g) was added into a solution of N-Boc piperazine (50 g) and 3-oxo-3-phenylpropanenitrile (19.49 g) in benzene (200 ml). The reaction mixture was heated up to 115° C. for 16 hours and resultant water was collected by Dean-Stark trap. After the solution was concentrated, a residue was obtained and further pur... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Enamine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | HO- | C1=CC=CC=C1 | 115 | null | CC(C)(C)OC(=O)N1CCNCC1.N#CCC(=O)c1ccccc1>C1=CC=CC=C1>CC(C)(C)OC(=O)N1CCN(C(=CC#N)c2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d21f6c4402e3420d8dff6e16a32fcaae | CC(C)(C)OC(=O)N1CCN(C(=CC#N)c2ccccc2)CC1>>N#CC=C(c1ccccc1)N1CCNCC1 | C(#N)C=C(C1=CC=CC=C1)N1CCN(CC1)C(=O)OC(C)(C)C>>C1(=CC=CC=C1)C(=CC#N)N1CCNCC1 | CC(C)(C)OC(=O)[N:14]1[CH2:13][CH2:12][N:11]([C:4](=[CH:3][C:2]#[N:1])[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:16][CH2:15]1>>[N:1]#[C:2][CH:3]=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1 | CC(C)(C)OC(=O)N1CCN(C(=CC#N)c2ccccc2)CC1 | N#CC=C(c1ccccc1)N1CCNCC1 | null | null | C(Cl)Cl.C(=O)(C(F)(F)F)O | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | [CH]=C(c1ccccc1)N1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | 1 | HOUR | tert-Butyl 4-(2-cyano-1-phenylvinyl)piperazine-1-carboxylate (600 mg) was dissolved in a 10% solution of TFA in methylene chloride (11 ml). After 1 hour at room temperature, the reaction mixture was partitioned between saturated NaHCO3 (20 ml) and EtOAc (20 ml), and the aqueous phase was extracted with EtOAc (3×20 ml).... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1 | HO- | C(Cl)Cl.C(=O)(C(F)(F)F)O | null | 1 | CC(C)(C)OC(=O)N1CCN(C(=CC#N)c2ccccc2)CC1>C(Cl)Cl.C(=O)(C(F)(F)F)O>N#CC=C(c1ccccc1)N1CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-38b7baa81a5a4dfba06ae10bb66987e8 | N#CC(C#N)=C(c1ccccc1)N1CCNCC1.O=C(Cl)C(=O)c1c[nH]c2cccc(F)c12>>N#CC(C#N)=C(c1ccccc1)N1CCN(C(=O)C(=O)c2c[nH]c3cccc(F)c23)CC1 | C(C)N(CC)CC.FC1=C2C(=CNC2=CC=C1)C(C(=O)Cl)=O.C1(=CC=CC=C1)C(=C(C#N)C#N)N1CCNCC1>>FC1=C2C(=CNC2=CC=C1)C(C(=O)N1CCN(CC1)C(=C(C#N)C#N)C1=CC=CC=C1)=O | [N:1]#[C:2][C:3]([C:4]#[N:5])=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[N:13]1[CH2:14][CH2:15][NH:16][CH2:31][CH2:32]1.Cl[C:17](=[O:18])[C:19](=[O:20])[c:21]1[cH:22][nH:23][c:24]2[cH:25][cH:26][cH:27][c:28]([F:29])[c:30]12>>[N:1]#[C:2][C:3]([C:4]#[N:5])=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[N:13]1[CH2:1... | N#CC(C#N)=C(c1ccccc1)N1CCNCC1.O=C(Cl)C(=O)c1c[nH]c2cccc(F)c12 | N#CC(C#N)=C(c1ccccc1)N1CCN(C(=O)C(=O)c2c[nH]c3cccc(F)c23)CC1 | null | null | C1CCOC1 | Acylation | N-alkylation of secondary amines with alkyl halides | fb1d4bfdc8484d3beb4f5a2f5f118fdb442bd6062c36ebdf1756cf55a6b42196 | 45bd90d69901afd73a792a8e298237e01711ace8aabc23c08b90247183376367 | C=C(c1ccccc1)N1CCN(C(=O)C(=O)c2c[nH]c3ccccc23)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[#7;a:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#7;a:7]:[c:6]:[c:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | 16 | HOUR | Triethyl amine (2 ml) was added into a solution of 2-(4-fluoro-1H-indol-3-yl)-2-oxoacetyl chloride (284 mg) and 2-(phenyl(piperazin-1-yl)methylene)malononitrile (300 mg) in dry THF (20 ml). After 16 hours, the reaction mixture was partitioned between saturated NaHCO3 (20 ml) and EtOAc (20 ml), and the aqueous phase was... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ketone.Secondary amine | Ketone.Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | HCl | C1CCOC1 | null | 16 | N#CC(C#N)=C(c1ccccc1)N1CCNCC1.O=C(Cl)C(=O)c1c[nH]c2cccc(F)c12>C1CCOC1>N#CC(C#N)=C(c1ccccc1)N1CCN(C(=O)C(=O)c2c[nH]c3cccc(F)c23)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-211a85b0eae84c81bc28ab31d4d18887 | N#CC(C#N)=C(c1ccccc1)N1CCNCC1.O=C(O)C(=O)c1c[nH]c2c(-n3ccnn3)ncc(F)c12>>N#CC(C#N)=C(c1ccccc1)N1CCN(C(=O)C(=O)c2c[nH]c3c(-n4ccnn4)ncc(F)c23)CC1 | CCN(C(C)C)C(C)C.FC1=C2C(=C(N=C1)N1N=NC=C1)NC=C2C(C(=O)O)=O.C1(=CC=CC=C1)C(=C(C#N)C#N)N1CCNCC1.C(C)OP(=O)(OCC)ON1N=NC2=C(C1=O)C=CC=C2>>FC1=C2C(=C(N=C1)N1N=NC=C1)NC=C2C(C(=O)N2CCN(CC2)C(=C(C#N)C#N)C2=CC=CC=C2)=O | [N:1]#[C:2][C:3]([C:4]#[N:5])=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[N:13]1[CH2:14][CH2:15][NH:16][CH2:36][CH2:37]1.O[C:17](=[O:18])[C:19](=[O:20])[c:21]1[cH:22][nH:23][c:24]2[c:25](-[n:26]3[cH:27][cH:28][n:29][n:30]3)[n:31][cH:32][c:33]([F:34])[c:35]12>>[N:1]#[C:2][C:3]([C:4]#[N:5])=[C:6]([c:7]1[cH:8][cH:9][c... | N#CC(C#N)=C(c1ccccc1)N1CCNCC1.O=C(O)C(=O)c1c[nH]c2c(-n3ccnn3)ncc(F)c12 | N#CC(C#N)=C(c1ccccc1)N1CCN(C(=O)C(=O)c2c[nH]c3c(-n4ccnn4)ncc(F)c23)CC1 | null | null | CN(C)C=O | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ec4549a741c3049bd1a976e49474da0a43114089beaee769b046eff196539f80 | 97511d740540e5b254d9cb7613bd570c71bcf3d9441b84419c4bf1beba0af4c8 | C=C(c1ccccc1)N1CCN(C(=O)C(=O)c2c[nH]c3c(-n4ccnn4)nccc23)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[#7;a:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#7;a:7]:[c:6]:[c:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | 16 | HOUR | 2-(4-fluoro-7-(1H-1,2,3-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetic acid (70 mg), 2-(phenyl(piperazin-1-yl)methylene)malononitrile (55 mg), 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT) (200 mg) and Hunig's Base (0.1 ml) were combined in 1.5 ml of DMF. The mixture was stirred at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Secondary amine | Ketone.Tertiary amide | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1c[nH]nn1.c1cc2cc[nH]c2cn1 | HO- | CN(C)C=O | null | 16 | N#CC(C#N)=C(c1ccccc1)N1CCNCC1.O=C(O)C(=O)c1c[nH]c2c(-n3ccnn3)ncc(F)c12>CN(C)C=O>N#CC(C#N)=C(c1ccccc1)N1CCN(C(=O)C(=O)c2c[nH]c3c(-n4ccnn4)ncc(F)c23)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2fb5853c35e0466c892e595cb8d83626 | N#CC(C#N)=C(Cl)c1ccccc1.O=C(C(=O)N1CCNCC1)c1c[nH]c2ccccc12>>N#CC(C#N)=C(c1ccccc1)N1CCN(C(=O)C(=O)c2c[nH]c3ccccc23)CC1 | C(C)N(CC)CC.N1C=C(C2=CC=CC=C12)C(C(=O)N1CCNCC1)=O.ClC(=C(C#N)C#N)C1=CC=CC=C1>>N1C=C(C2=CC=CC=C12)C(C(=O)N1CCN(CC1)C(=C(C#N)C#N)C1=CC=CC=C1)=O | Cl[C:6](=[C:3]([C:2]#[N:1])[C:4]#[N:5])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[NH:13]1[CH2:14][CH2:15][N:16]([C:17](=[O:18])[C:19](=[O:20])[c:21]2[cH:22][nH:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1>>[N:1]#[C:2][C:3]([C:4]#[N:5])=[C:6]([c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1)[N:13]1[CH2:14][CH... | N#CC(C#N)=C(Cl)c1ccccc1.O=C(C(=O)N1CCNCC1)c1c[nH]c2ccccc12 | N#CC(C#N)=C(c1ccccc1)N1CCN(C(=O)C(=O)c2c[nH]c3ccccc23)CC1 | null | null | CCO | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 22151336be5c8e8ab15ce2990713f7ae70624479d21088590ca38d3d2f1591e5 | 24343b493406f30850a2e160dec6759b529ccec020e35365ba8d762a5dbc1073 | C=C(c1ccccc1)N1CCN(C(=O)C(=O)c2c[nH]c3ccccc23)CC1 | Cl-[C;H0;D3;+0:1](=[C:2](-[C:3]#[N;D1;H0:4])-[C:5]#[N;D1;H0:6])-[c:7](:[c:8]):[c:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[N;D1;H0:4]#[C:3]-[C:2](-[C:5]#[N;D1;H0:6])=[C;H0;D3;+0:1](-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-1)-[c:7](:[c:8]):[c:9] | null | [] | null | null | 16 | HOUR | Triethyl amine (1 ml) was added into a solution of 1-(1H-indol-3-yl)-2-(piperazin-1-yl)ethane-1,2-dione (150 mg) and 2-(chloro(phenyl)methylene)malononitrile (110 mg) in EtOH (20 ml). After 16 hours at 115° C., the reaction mixture was cooled down. Then the solvents were removed to offer a residue which was purified us... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Secondary amine | Enamine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | HCl | CCO | null | 16 | N#CC(C#N)=C(Cl)c1ccccc1.O=C(C(=O)N1CCNCC1)c1c[nH]c2ccccc12>CCO>N#CC(C#N)=C(c1ccccc1)N1CCN(C(=O)C(=O)c2c[nH]c3ccccc23)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-066d3d069d40475f9aacc75728eab20e | COc1cccc(OC)c1O.O=C1CCC(=O)N1Br>>COc1cc(Br)cc(OC)c1O | COC1=C(C(=CC=C1)OC)O.BrN1C(CCC1=O)=O>>BrC1=CC(=C(C(=C1)OC)O)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:7][c:8]([O:9][CH3:10])[c:11]1[OH:12].O=C1CCC(=O)N1[Br:6]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Br:6])[cH:7][c:8]([O:9][CH3:10])[c:11]1[OH:12] | COc1cccc(OC)c1O.O=C1CCC(=O)N1Br | COc1cc(Br)cc(OC)c1O | null | null | C(Cl)Cl | Functional Group Interconversion | Bromination | 48c1dcf50945076da40bbd7976060ec1ea74b3478ef8c25d67664232b218095c | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[c:2]:[c:3]:[cH;D2;+0:4]:[c:5]:[c:6]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:4](:[c:3]:[c:2]):[c:5]:[c:6] | null | [] | -78 | CELSIUS | 4 | HOUR | To a cooled (−78° C.) solution of 2,6-dimetoxyphenol (13)(15 g, 97.35 mmol) in CH2Cl2 (200 ml) was added N-bromosuccinimide (17.4 g, 97.35 mmol) portionwise over twenty minutes. The reaction mixture was stirred at −78° C. under an inert atmosphere for four hours before being allowed to warm to room temperature where it... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccccc1.C1CCNC1 | c1ccccc1 | c1ccccc1 | HO- | C(Cl)Cl | -78 | 4 | COc1cccc(OC)c1O.O=C1CCC(=O)N1Br>C(Cl)Cl>COc1cc(Br)cc(OC)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-17fe669a02fd4025b1fe360eec5247ad | Brc1c[nH]cn1.Clc1nc(N2CCOCC2)nc(N2CCOCC2)n1>>BrC1=CN(c2nc(N3CCOCC3)nc(N3CCOCC3)n2)CN1 | BrC=1N=CNC1.[H-].[Na+].ClC1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1>>BrC=1NCN(C1)C1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1 | [Br:1][c:2]1[cH:3][nH:4][cH:23][n:24]1.Cl[c:5]1[n:6][c:7]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[n:14][c:15]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[n:22]1>>[Br:1][C:2]1=[CH:3][N:4]([c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[n:14][c:15]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[... | Brc1c[nH]cn1.Clc1nc(N2CCOCC2)nc(N2CCOCC2)n1 | BrC1=CN(c2nc(N3CCOCC3)nc(N3CCOCC3)n2)CN1 | null | null | O.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | f248f02f64c800c6f2e6b7c1717b14928ba91aa33dd9744d64abc358b0052acd | 73dea3bf6cead304fe87113eac383fc85bbcb21234d3dcdab06f3b60c1fb5569 | C1=CN(c2nc(N3CCOCC3)nc(N3CCOCC3)n2)CN1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[#7;a:7]:1.[Br;D1;H0:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[nH;D2;+0:11]:[cH;D2;+0:12]:[n;H0;D2;+0:13]:1>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]2-[CH2;D2;+0:12]-[NH;D2;+0:13]-[C;H0;D3;+0:9](-[Br;D1;H0:8])=[CH;D2;+0:10]-2):[#7;a:2]:1 | null | [] | 120 | CELSIUS | null | null | To a cooled solution of 4-bromo-1H-imidazole (0.249 g, 2.0 mmol) in anhydrous dimethylformamide (4 ml) was slowly added sodium hydride (60% dispersion in mineral oil) (0.088 g, 2.2 mmol). When the evolution of gas has ceased (30 mins), 2-chloro-4,6-di-morpholin-4-yl-[1,3,5]triazine (3b)(0.571 g, 2.00 mmol) was added in... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | Enamine.Enamine.Alkenyl halide | c1c[nH]cn1.c1ncncn1 | C1=C[NH]CN1.c1ncncn1 | C1=C[NH]CN1.c1ncncn1.C1COCC[NH]1.C1COCC[NH]1 | Other | O.CN(C=O)C | 120 | null | Brc1c[nH]cn1.Clc1nc(N2CCOCC2)nc(N2CCOCC2)n1>O.CN(C=O)C>BrC1=CN(c2nc(N3CCOCC3)nc(N3CCOCC3)n2)CN1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-615c3aa143234bda9e401a7d4278a91e | Brc1cn[nH]c1.Clc1nc(N2CCOCC2)nc(N2CCOCC2)n1>>Brc1cnn(-c2nc(N3CCOCC3)nc(N3CCOCC3)n2)c1 | BrC=1C=NNC1.[H-].[Na+].ClC1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1>>BrC=1C=NN(C1)C1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1 | [Br:1][c:2]1[cH:3][n:4][nH:5][cH:24]1.Cl[c:6]1[n:7][c:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[n:15][c:16]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[n:23]1>>[Br:1][c:2]1[cH:3][n:4][n:5](-[c:6]2[n:7][c:8]([N:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)[n:15][c:16]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:... | Brc1cn[nH]c1.Clc1nc(N2CCOCC2)nc(N2CCOCC2)n1 | Brc1cnn(-c2nc(N3CCOCC3)nc(N3CCOCC3)n2)c1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 245d3e640f59c763fdeb8bd6a6c7a48c60f9fe368160bdf9907bb43c19968e5d | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1cnn(-c2nc(N3CCOCC3)nc(N3CCOCC3)n2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7:4]):[#7;a:5]:[c:6]:[#7;a:7]:1.[#7;a:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1>>[#7:4]-[c:3]1:[#7;a:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:1](-[n;H0;D3;+0:12]2:[#7;a:8]:[c:9]:[c:10]:[c:11]:2):[#7;a:2]:1 | 92.4 | [{"value": 92.4, "product": "BrC=1C=NN(C1)C1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.1, "product": "BrC=1C=NN(C1)C1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a cooled (0° C.) solution of 4-bromopyrazole (0.29 g, 2.0 mmol) in anhydrous DMF (4 ml) was added NaH (60% dispersion in mineral oil, 0.088 g, 2.2 mmol) in a portionwise fashion over 10 minutes. The mixture allowed to warm to room temperature where it was stirred for 30 minutes before the adition of 2-Chloro-4,6-di-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cn[nH]c1.c1ncncn1 | c1cn[nH]c1.c1ncncn1 | c1cn[nH]c1.c1ncncn1.C1COCC[NH]1.C1COCC[NH]1 | HCl | O.CN(C)C=O | null | null | Brc1cn[nH]c1.Clc1nc(N2CCOCC2)nc(N2CCOCC2)n1>O.CN(C)C=O>Brc1cnn(-c2nc(N3CCOCC3)nc(N3CCOCC3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a7dda5cdea14111b7d1063352b9ecea | C1COCCN1.Clc1ccnc(Cl)n1>>Clc1nccc(N2CCOCC2)n1 | ClC1=NC=CC(=N1)Cl.C(C)N(CC)CC.N1CCOCC1>>ClC1=NC=CC(=N1)N1CCOCC1 | [NH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1.Cl[c:6]1[cH:5][cH:4][n:3][c:2]([Cl:1])[n:13]1>>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[n:13]1 | C1COCCN1.Clc1ccnc(Cl)n1 | Clc1nccc(N2CCOCC2)n1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | b6ba2533a469a91b7ece94b4a523fa9d9d9bc584236787b5a2be96cdf7a917fc | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(N2CCOCC2)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1.[#8:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[Cl;D1;H0:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]2-[C:10]-[C:9]-[#8:8]-[C:13]-[C:12]-2):[c:7]:[c:6]:[#7;a:5]:1 | 90.5 | [{"value": 90.0, "product": "ClC1=NC=CC(=N1)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.5, "product": "ClC1=NC=CC(=N1)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a cooled (0° C.) suspension of 2,4-dichloropyrimidine (20)(1.0 g, 6.7 mmol) in ethanol (20 ml), which was stirred under an inert atmosphere, was added triethylamine (1.4 ml, 10.1 mmol) and then morpholine (0.59 ml, 6.7 mmol). The mixture was maintained at this temperature for 3 hours whereupon it was concentrated in... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1cncnc1 | c1cncnc1.C1COCC[NH]1 | c1cncnc1.C1COCC[NH]1 | HCl | C(C)O | null | null | C1COCCN1.Clc1ccnc(Cl)n1>C(C)O>Clc1nccc(N2CCOCC2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e4859d64ceb545569fb5aa9671242aef | Brc1cn[nH]c1.Clc1nccc(N2CCOCC2)n1>>Brc1cnn(-c2nccc(N3CCOCC3)n2)c1 | O.[H-].[Na+].BrC=1C=NNC1.ClC1=NC=CC(=N1)N1CCOCC1>>BrC=1C=NN(C1)C1=NC=CC(=N1)N1CCOCC1 | [Br:1][c:2]1[cH:3][n:4][nH:5][cH:18]1.Cl[c:6]1[n:7][cH:8][cH:9][c:10]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[n:17]1>>[Br:1][c:2]1[cH:3][n:4][n:5](-[c:6]2[n:7][cH:8][cH:9][c:10]([N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[n:17]2)[cH:18]1 | Brc1cn[nH]c1.Clc1nccc(N2CCOCC2)n1 | Brc1cnn(-c2nccc(N3CCOCC3)n2)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 1bafe9814f38573617702c535870830ada71694bc4a8646acfa1e8fd935c7e26 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1cnn(-c2nccc(N3CCOCC3)n2)c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#7;a:6]1:[c:7]:[c:8]:[c:9]:[nH;D2;+0:10]:1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[n;H0;D3;+0:10]1:[#7;a:6]:[c:7]:[c:8]:[c:9]:1):[#7;a:4]:[c:5] | 93 | [{"value": 93.0, "product": "BrC=1C=NN(C1)C1=NC=CC(=N1)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "BrC=1C=NN(C1)C1=NC=CC(=N1)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 30 | MINUTE | To a cooled (0° C.) solution of 4-bromo-1H-pyrazole (0.74 g, 5.0 mmol) in anhydrous DMF (7 ml) was added NaH (60% dispersion in mineral oil, 0.22 g, 5.5 mmol) in a portionwise fashion over 10 minutes. The mixture was stirred like this for 30 minutes before the addition of 4-(2-chloro-pyrimidin-4-yl)-morpholine (21)(1.0... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cn[nH]c1.c1cncnc1 | c1cn[nH]c1.c1cncnc1 | c1cn[nH]c1.c1cncnc1.C1COCC[NH]1 | HCl | CN(C)C=O | 120 | 0.5 | Brc1cn[nH]c1.Clc1nccc(N2CCOCC2)n1>CN(C)C=O>Brc1cnn(-c2nccc(N3CCOCC3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6483d471942f45de88adb81834180996 | Brc1csc(Br)n1.Clc1ccnc(Cl)n1>>Clc1nccc(-c2nc(Br)cs2)n1 | C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N.[OH-].[Na+].O.C(CCC)[Li].ClC1=NC=CC(=N1)Cl.BrC=1SC=C(N1)Br>>BrC=1N=C(SC1)C1=NC(=NC=C1)Cl | Br[c:7]1[n:8][c:9]([Br:10])[cH:11][s:12]1.Cl[c:6]1[cH:5][cH:4][n:3][c:2]([Cl:1])[n:13]1>>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]([Br:10])[cH:11][s:12]2)[n:13]1 | Brc1csc(Br)n1.Clc1ccnc(Cl)n1 | Clc1nccc(-c2nc(Br)cs2)n1 | null | null | C(C)OCC.C1CCOC1 | C-C Coupling | OtherReaction | abe34db7de0cd3e25b9dfb203c87b62f1083867711857e7e9e860c85218983b5 | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | c1cc(-c2nccs2)ncn1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.Cl-[c;H0;D3;+0:6]1:[#7;a:7]:[c:8](-[Cl;D1;H0:9]):[#7;a:10]:[c:11]:[c:12]:1>>[Cl;D1;H0:9]-[c:8]1:[#7;a:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1]2:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:2):[c:12]:[c:11]:[#7;a:10]:1 | 76.8 | [{"value": 69.8, "product": "BrC=1N=C(SC1)C1=NC(=NC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.8, "product": "BrC=1N=C(SC1)C1=NC(=NC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a cooled (−78° C.) solution of 2,4-dibromothiazole (24)(0.73 g, 3.0 mmol) in anhydrous diethylether (7 ml) was added n-butyllithium (2.5M in hexane, 1.5 ml, 3.28 mmol) in a dropwise fashion via syringe. The yellow solution was stirred at −78° C. for 15 minutes before the addition of a suspension of 2-chloropyrimidin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1cscn1.c1cncnc1 | c1cncnc1.c1cscn1 | c1cncnc1.c1cscn1 | Br- | C(C)OCC.C1CCOC1 | null | 16 | Brc1csc(Br)n1.Clc1ccnc(Cl)n1>C(C)OCC.C1CCOC1>Clc1nccc(-c2nc(Br)cs2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3a6759d305be419e92d2860eee056958 | C1COCCN1.Clc1nccc(-c2nc(Br)cs2)n1>>Brc1csc(-c2ccnc(N3CCOCC3)n2)n1 | BrC=1N=C(SC1)C1=NC(=NC=C1)Cl.C([O-])([O-])=O.[K+].[K+].N1CCOCC1>>BrC=1N=C(SC1)C1=NC(=NC=C1)N1CCOCC1 | [NH:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1.Cl[c:10]1[n:9][cH:8][cH:7][c:6](-[c:5]2[s:4][cH:3][c:2]([Br:1])[n:18]2)[n:17]1>>[Br:1][c:2]1[cH:3][s:4][c:5](-[c:6]2[cH:7][cH:8][n:9][c:10]([N:11]3[CH2:12][CH2:13][O:14][CH2:15][CH2:16]3)[n:17]2)[n:18]1 | C1COCCN1.Clc1nccc(-c2nc(Br)cs2)n1 | Brc1csc(-c2ccnc(N3CCOCC3)n2)n1 | null | null | CCO | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | b6ba2533a469a91b7ece94b4a523fa9d9d9bc584236787b5a2be96cdf7a917fc | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(-c2nccs2)nc(N2CCOCC2)n1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1):[#7;a:4]:[c:5] | 30.6 | [{"value": 30.5, "product": "BrC=1N=C(SC1)C1=NC(=NC=C1)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.6, "product": "BrC=1N=C(SC1)C1=NC(=NC=C1)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | To a solution of 4-(4-Bromo-thiazol-2-yl)-2-chloro-pyrimidine (25)(0.498 g, 1.8 mmol) in EtOH (8 ml) was added powdered potassium carbonate (0.274 g, 1.98 mmol) and morpholine (0.17 ml, 1.98 mmol). The mixture was heated under the influence of microwave radiation (10 minutes, 90° C., high absorption setting). The react... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1cncnc1 | c1cncnc1.C1COCC[NH]1 | c1cscn1.c1cncnc1.C1COCC[NH]1 | HCl | CCO | 90 | null | C1COCCN1.Clc1nccc(-c2nc(Br)cs2)n1>CCO>Brc1csc(-c2ccnc(N3CCOCC3)n2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fd0e1166775446329d0e06439d41bdf5 | Brc1c[nH]cn1.Clc1nccc(N2CCOCC2)n1>>Brc1cn(-c2nccc(N3CCOCC3)n2)cn1 | ClC1=NC=CC(=N1)N1CCOCC1.BrC=1N=CNC1.CN(C)C=O.[H-].[Na+]>>BrC=1N=CN(C1)C1=NC=CC(=N1)N1CCOCC1 | [Br:1][c:2]1[cH:3][nH:4][cH:17][n:18]1.Cl[c:5]1[n:6][cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[n:16]1>>[Br:1][c:2]1[cH:3][n:4](-[c:5]2[n:6][cH:7][cH:8][c:9]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[n:16]2)[cH:17][n:18]1 | Brc1c[nH]cn1.Clc1nccc(N2CCOCC2)n1 | Brc1cn(-c2nccc(N3CCOCC3)n2)cn1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | e64c0bd3880a16dae8dbdce158f5a8057eade05f62dc3f1bd7056598cea48127 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1cn(-c2nccc(N3CCOCC3)n2)cn1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[Br;D1;H0:6]-[c:7]1:[#7;a:8]:[c:9]:[nH;D2;+0:10]:[c:11]:1>>[Br;D1;H0:6]-[c:7]1:[#7;a:8]:[c:9]:[n;H0;D3;+0:10](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:11]:1 | 94.4 | [{"value": 94.4, "product": "BrC=1N=CN(C1)C1=NC=CC(=N1)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.3, "product": "BrC=1N=CN(C1)C1=NC=CC(=N1)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | To a cooled (0° C.) solution of 4-bromo-1-H-imidazole (0.8 g, 4.0 mmol) in anhydrous DMF (5.0 mmol) was added NaH (60% dispersion in mineral oil, 0.176 g, 4.4 mmol) in a portionwise fashion over 10 minutes. When gas evolution had ceased, 4-(2-Chloro-pyrimidin-4-yl)-morpholine (21)(0.79 g, 4.00 mmol) was added and the m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1cncnc1 | c1c[nH]cn1.c1cncnc1 | c1c[nH]cn1.c1cncnc1.C1COCC[NH]1 | HCl | O | 120 | null | Brc1c[nH]cn1.Clc1nccc(N2CCOCC2)n1>O>Brc1cn(-c2nccc(N3CCOCC3)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-52fe52bb7b304fe7970cc8b40a43952c | CC(N)=O.O=C(O)c1ccncc1C(=O)O>>O=C1NC(=O)c2cnccc21 | C1=CN=CC(=C1C(=O)O)C(=O)O.C(C)(=O)OC(C)=O.C(C)(=O)N>>C1(NC(C=2C=NC=CC21)=O)=O | CC(=O)[NH2:3].O=[C:4]([OH:5])[c:6]1[cH:7][n:8][cH:9][cH:10][c:11]1[C:2](O)=[O:1]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[cH:7][n:8][cH:9][cH:10][c:11]21 | CC(N)=O.O=C(O)c1ccncc1C(=O)O | O=C1NC(=O)c2cnccc21 | null | null | null | Acylation | OtherReaction | 43b6b5d6adef6ba7cb5e531c3a02fe0b90a46df1821ce71e6c55d3c3bdfdbf2a | 77a5badbeb951d592954b9740fc504e79325b67a2746c9485dc5b63285d2756d | O=C1NC(=O)c2cnccc21 | C-C(=O)-[NH2;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1-[C;H0;D3;+0:10](=O)-[OH;D1;+0:11]>>[O;D1;H0:3]=[C;H0;D3;+0:2]1-[NH;D2;+0:1]-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[c:9]2:[c:8]:[#7;a:7]:[c:6]:[c:5]:[c:4]:2-1 | 95.1 | [{"value": 95.1, "product": "C1(NC(C=2C=NC=CC21)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.1, "product": "C1(NC(C=2C=NC=CC21)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 145 | CELSIUS | null | null | A suspension of cinchomeronic acid (30)(50 g, 300 mmol) in acetic anhydride (123.5 g, 1200 mmol) was heated to reflux (140-150° C.) until all solid material dissolved and the mixture was homogeneous. The mixture was then cooled and concentrated in vacuo. Acetamide (50 g, 846 mmol) was then added and the mixture heated ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amide | Unsubstituted dicarboximide | null | c1cc2c(cn1)CNC2 | c1cc2c(cn1)CNC2 | HO- | null | 145 | null | CC(N)=O.O=C(O)c1ccncc1C(=O)O>>O=C1NC(=O)c2cnccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-032bca659f594568b03efd61c7c2bb57 | N=CN.Nc1cnccc1C(=O)O>>Oc1ncnc2cnccc12 | NC1=C(C(=O)O)C=CN=C1.C(C)(=O)O.C(=N)N.C([O-])(O)=O.[Na+]>>N1=CN=C(C2=C1C=NC=C2)O | N[CH:4]=[NH:3].O=[C:2]([OH:1])[c:11]1[c:6]([NH2:5])[cH:7][n:8][cH:9][cH:10]1>>[OH:1][c:2]1[n:3][cH:4][n:5][c:6]2[cH:7][n:8][cH:9][cH:10][c:11]12 | N=CN.Nc1cnccc1C(=O)O | Oc1ncnc2cnccc12 | null | null | CC(=O)N(C)C | Aromatic Heterocycle Formation | OtherReaction | 5983bafb4e77f03ec2615bba50d52afd890f9ca3d277cb83c5de11a3b0833daf | 6a90cec53d476b6db41cf916b335df590ac09cb14a5414b8e4682f8f72909dd8 | c1cc2cncnc2cn1 | N-[CH;D2;+0:1]=[NH;D1;+0:2].O=[C;H0;D3;+0:3](-[O;D1;H1:4])-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1-[NH2;D1;+0:11]>>[O;D1;H1:4]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:2]:[cH;D2;+0:1]:[n;H0;D2;+0:11]:[c:10]2:[c:9]:[#7;a:8]:[c:7]:[c:6]:[c:5]:2:1 | 87.63 | [{"value": 87.63, "product": "N1=CN=C(C2=C1C=NC=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.6, "product": "N1=CN=C(C2=C1C=NC=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | A mixture of 3-amino-isonicotinic acid (32)(26.24 g, 190.0 mmol) and formamidine acetate (39.56 g, 380 mmol) in dimethylacetamide (100 ml) was stirred and heated to 150° C. The reaction was maintained at this temperature with stirring for 12 hours before it was allowed to cool to 25° C. and then basified with sodium bi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine.Primary amine | Aromatic alcohol | c1ccncc1 | c1cc2cncnc2cn1 | c1cc2cncnc2cn1 | HO- | CC(=O)N(C)C | 150 | null | N=CN.Nc1cnccc1C(=O)O>CC(=O)N(C)C>Oc1ncnc2cnccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-694e1296ac2d4f1a85bd1ff5e3a2b47a | O=S(Cl)Cl.Oc1ncnc2cnccc12>>Clc1ncnc2cnccc12 | N1=CN=C(C2=C1C=NC=C2)O.S(=O)(Cl)Cl>>ClC=1C2=C(N=CN1)C=NC=C2 | O=S(Cl)[Cl:1].O[c:2]1[n:3][cH:4][n:5][c:6]2[cH:7][n:8][cH:9][cH:10][c:11]12>>[Cl:1][c:2]1[n:3][cH:4][n:5][c:6]2[cH:7][n:8][cH:9][cH:10][c:11]12 | O=S(Cl)Cl.Oc1ncnc2cnccc12 | Clc1ncnc2cnccc12 | null | null | CN(C=O)C | Functional Group Interconversion | Alcohol to chloride_SOCl2 | 379ad084598c3abf990ee575bd8ec80c282f2a41f0cbf6134a97b9b785c01ef8 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1cc2cncnc2cn1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:[#7;a:8]:[c:9]:[c:10]:[c:11]:2:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:[#7;a:8]:[c:9]:[c:10]:[c:11]:2:1 | 99.4 | [{"value": 99.4, "product": "ClC=1C2=C(N=CN1)C=NC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of pyrido[3,4-d]pyrimidin-4-ol (33)(1.47 g, 10 mmol) in thionylchloride (30 ml) and dimethylformamide (50 μl, cat.) was heated to reflx (90° C.) for 1 hour. The mixture was then cooled and concentrated in vacuo and then diluted with CH2Cl2 (50 ml) which caused a suspension to form. The solid was removed by... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cc2cncnc2cn1 | c1cc2cncnc2cn1 | c1cc2cncnc2cn1 | HCl | CN(C=O)C | null | null | O=S(Cl)Cl.Oc1ncnc2cnccc12>CN(C=O)C>Clc1ncnc2cnccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-287bfa590a71430eb724d3040f8e4c30 | Clc1ncnc2cnccc12.NN>>NNc1ncnc2cnccc12 | ClC=1C2=C(N=CN1)C=NC=C2.NN>>N1=CN=C(C2=C1C=NC=C2)NN | Cl[c:3]1[n:4][cH:5][n:6][c:7]2[cH:8][n:9][cH:10][cH:11][c:12]12.[NH2:1][NH2:2]>>[NH2:1][NH:2][c:3]1[n:4][cH:5][n:6][c:7]2[cH:8][n:9][cH:10][cH:11][c:12]12 | Clc1ncnc2cnccc12.NN | NNc1ncnc2cnccc12 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | a9e93654e0985130bf9394ef9c97e19eab53d69ddd07f7ddf79f62aef60f7349 | 61806bbf8bb8981e140ee503663af0ef0e69dc4f34f6582f974a2e4218f7da88 | c1cc2cncnc2cn1 | 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.[N;D1;H2:11]-[NH2;D1;+0:12]>>[N;D1;H2:11]-[NH;D2;+0:12]-[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 | 96.9 | [{"value": 96.9, "product": "N1=CN=C(C2=C1C=NC=C2)NN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.8, "product": "N1=CN=C(C2=C1C=NC=C2)NN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a suspension of 4-Chloro-pyrido[3,4-d]pyrimidine (34)(1.65 g, 10 mmol) in anhydrous THF (10 ml) was added hydrazine (1M in THF, 30 ml, 30 mmol). The reaction mixture was stirred at room temperature for 5 hours whereupon a yellow precipitate formed. The solid was removed by filtration, washed with cold THF (10 ml) an... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide | Hydrazine | c1cc2cncnc2cn1 | c1cc2cncnc2cn1 | c1cc2cncnc2cn1 | HCl | C1CCOC1 | null | 5 | Clc1ncnc2cnccc12.NN>C1CCOC1>NNc1ncnc2cnccc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-910ef591d58d402f9d4f2ab8fd7ea233 | COCCO.Cc1cc(N)c(C(=O)O)cc1C.N=CN>>COc1cc2ncnc(O)c2cc1OC | NC1=C(C(=O)O)C=C(C(=C1)C)C.C(C)(=O)O.C(=N)N.COCCO>>COC=1C=C2C(=NC=NC2=CC1OC)O | C([CH2:1][OH:2])[O:14][CH3:15].C[c:3]1[cH:4][c:5]([NH2:6])[c:11]([C:9](=O)[OH:10])[cH:12][c:13]1C.N[CH:7]=[NH:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([OH:10])[c:11]2[cH:12][c:13]1[O:14][CH3:15] | COCCO.Cc1cc(N)c(C(=O)O)cc1C.N=CN | COc1cc2ncnc(O)c2cc1OC | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 95797d028ec933c0882fb4f6ae9edc5f6d59c5307ec06a2be881de9d669f7f4d | 9aaf9bbc14b4e82110f3bb8f121adfdcc23ebe1e85b49970f28f2996cc7467b5 | c1ccc2ncncc2c1 | C-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[C;H0;D3;+0:4](=O)-[O;D1;H1:5]):[c:6](-[NH2;D1;+0:7]):[c:8]:[c;H0;D3;+0:9]:1-C.N-[CH;D2;+0:10]=[NH;D1;+0:11].[C;D1;H3:12]-[O;H0;D2;+0:13]-C-[CH2;D2;+0:14]-[OH;D1;+0:15]>>[C;D1;H3:12]-[O;H0;D2;+0:13]-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[c:6](:[c:8]:[c;H0;D3;+0:9]:1-[O;H0;D2;+0:15]-[CH3;D1;+0:14])... | 86.2 | [{"value": 86.2, "product": "COC=1C=C2C(=NC=NC2=CC1OC)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-amino-4,5-dimethylbenzoic acid (37)(5 g, 25.30 mmol) and formamidine acetate (5.2 g, 50.00 mmol) were dissolved in 2-methoxyethanol (80 ml) and the mixture heated to reflux for 16 hours. The mixture was cooled and concentrated in vacuo and suspended in a small volume of water. Sodium bicarbonate (5% aqueous solution)... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Primary alcohol.Primary amine.Primary amine | Ether.Ether.Aromatic alcohol | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HO- | null | null | null | COCCO.Cc1cc(N)c(C(=O)O)cc1C.N=CN>>COc1cc2ncnc(O)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee1961e04388462793459e5e4568c33e | COc1cc2ncnc(O)c2cc1OC.ClCCCl>>COc1cc2ncnc(Cl)c2cc1OC | COC=1C=C2C(=NC=NC2=CC1OC)O.ClCCCl.C(C)(C)NC(C)C>>ClC1=NC=NC2=CC(=C(C=C12)OC)OC | O[c:9]1[n:8][cH:7][n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH3:15])[cH:12][c:11]21.ClCC[Cl:10]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([Cl:10])[c:11]2[cH:12][c:13]1[O:14][CH3:15] | COc1cc2ncnc(O)c2cc1OC.ClCCCl | COc1cc2ncnc(Cl)c2cc1OC | null | null | null | Functional Group Interconversion | Alcohol to chloride_Other | 160b9695b43da4320d92d63672a7a1481353e8305872af69b78f6687a62557ef | 74bb11031f02e9bea6212ccc07d644e568e549286fe7002f9fa7c0d1b5bcfcd9 | c1ccc2ncncc2c1 | Cl-C-C-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a: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:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | 88.9 | [{"value": 88.9, "product": "ClC1=NC=NC2=CC(=C(C=C12)OC)OC", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a suspension of 6,7-Dimethoxy-quinazolin-4-ol (1.65 g, 8.0 mmol) and phosporousoxychloride (1.52 ml, 16.4 mmol) in 1,2-dichloroethane (16 ml) was added diisopropylamine (3.48 ml, 20 mmol) in a dropwise fashion. The mixture was then heated to 80° C. under an inert atmosphere for 16 hours. After this time the reaction... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Aromatic alcohol | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HCl | null | 80 | null | COc1cc2ncnc(O)c2cc1OC.ClCCCl>>COc1cc2ncnc(Cl)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a30a485362424c4b8517d06d2a1f8278 | COc1cc2ncnc(Cl)c2cc1OC.NN>>COc1cc2ncnc(NN)c2cc1OC | ClC1=NC=NC2=CC(=C(C=C12)OC)OC.NN>>COC=1C=C2C(=NC=NC2=CC1OC)NN | Cl[c:9]1[n:8][cH:7][n:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:14]([O:15][CH3:16])[cH:13][c:12]21.[NH2:10][NH2:11]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[n:6][cH:7][n:8][c:9]([NH:10][NH2:11])[c:12]2[cH:13][c:14]1[O:15][CH3:16] | COc1cc2ncnc(Cl)c2cc1OC.NN | COc1cc2ncnc(NN)c2cc1OC | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 128faa8280e3694e54b70337c600ffe20c2c3650cfe2162f4ea879a74a34b2e6 | 61806bbf8bb8981e140ee503663af0ef0e69dc4f34f6582f974a2e4218f7da88 | c1ccc2ncncc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[N;D1;H2:9]-[NH2;D1;+0:10]>>[N;D1;H2:9]-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8] | 91 | [{"value": 91.0, "product": "COC=1C=C2C(=NC=NC2=CC1OC)NN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.3, "product": "COC=1C=C2C(=NC=NC2=CC1OC)NN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a suspension of 4-Chloro-6,7-dimethoxy-quinazoline (0.20 g, 0.89 mmol) in anhydrous THF (0.5 ml) was added hydrazine (1M in THF, 2.0 ml, 2.0 mmol). The mixture was stirred at room temperature for 16 hours whereupon a precipitate had formed which was removed by filtration and washed with cold THF to give the desired ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide | Hydrazine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HCl | C1CCOC1 | null | 16 | COc1cc2ncnc(Cl)c2cc1OC.NN>C1CCOC1>COc1cc2ncnc(NN)c2cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f308ab084e7e4581ab6ea97ce1ef1c30 | BrCCOCCBr.Nc1cccc([N+](=O)[O-])c1>>O=[N+]([O-])c1cccc(N2CCOCC2)c1 | [N+](=O)([O-])C=1C=C(N)C=CC1.BrCCOCCBr.C(C)(C)N(C(C)C)CC>>[N+](=O)([O-])C=1C=C(C=CC1)N1CCOCC1 | Br[CH2:10][CH2:11][O:12][CH2:13][CH2:14]Br.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([NH2:9])[cH:15]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15]1 | BrCCOCCBr.Nc1cccc([N+](=O)[O-])c1 | O=[N+]([O-])c1cccc(N2CCOCC2)c1 | null | null | C(Cl)Cl.CC(=O)N(C)C | Heteroatom Alkylation and Arylation | OtherReaction | 96e983e5a21a49df63baecef913e7d3b8dacd6365c270725738379ba775c02bb | 631870b1ab33be0edc94bc9ae10321f1c5ede4dd4db77035c9d3979e4a2118fb | c1ccc(N2CCOCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-Br.[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[N;H0;D3;+0:6]1-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-1):[c:9] | 100 | [{"value": 79.7, "product": "[N+](=O)([O-])C=1C=C(C=CC1)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.0, "product": "[N+](=O)([O-])C=1C=C(C=CC1)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | To a solution of 3-nitroaniline (42)(5.52 g, 40.00 mmol) in anhydrous dimethylacetamide (15 ml) was added 2-bromoethylether (7.52 ml, 60.00 mmol) and N,N-diisopropylethylamine (13.94 ml, 80.0 mmol). The mixture was then heated to 120° C. for 6 hours. After this time the reaction was cooled to room temperature which saw... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Primary amine | Tertiary amine | null | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HBr | C(Cl)Cl.CC(=O)N(C)C | 120 | null | BrCCOCCBr.Nc1cccc([N+](=O)[O-])c1>C(Cl)Cl.CC(=O)N(C)C>O=[N+]([O-])c1cccc(N2CCOCC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8513643c609c4e298d82a8cb8e6aed0e | O=[N+]([O-])c1cccc(N2CCOCC2)c1>>Nc1cccc(N2CCOCC2)c1 | [N+](=O)([O-])C=1C=C(C=CC1)N1CCOCC1>>N1(CCOCC1)C=1C=C(C=CC1)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13]1>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[cH:13]1 | O=[N+]([O-])c1cccc(N2CCOCC2)c1 | Nc1cccc(N2CCOCC2)c1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCOCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 95.2 | [{"value": 95.2, "product": "N1(CCOCC1)C=1C=C(C=CC1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.1, "product": "N1(CCOCC1)C=1C=C(C=CC1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a cooled (0° C.) solution of 4-(3-nitro-phenyl)-morpholine (43)(4.16 g, 20 mmol) in methanol (50 ml) was added Pd/C (10% loading, 460 mg). The mixture was stirred at room temperature under an H2 (1 atm) for 16 hrs. The mixture was then filtered through a Celite™ pad, the filtrate dried using MgSO4, filtered and conc... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.C1COCC[NH]1 | Other | [Pd].CO | null | 16 | O=[N+]([O-])c1cccc(N2CCOCC2)c1>[Pd].CO>Nc1cccc(N2CCOCC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c99b7303929b490fb4c110647f7dc8c3 | Nc1cccc(N2CCOCC2)c1>>NNc1cccc(N2CCOCC2)c1 | [OH-].[Na+].N(=O)[O-].[Na+].N1(CCOCC1)C=1C=C(C=CC1)N.O.O.[Sn](Cl)Cl>>N1(CCOCC1)C=1C=C(C=CC1)NN | [NH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[cH:14]1>>[NH2:1][NH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[cH:14]1 | Nc1cccc(N2CCOCC2)c1 | NNc1cccc(N2CCOCC2)c1 | null | null | Cl | Miscellaneous | OtherReaction | c4079cd46dafde13b56adeac363106820ab4184dee8b1ca632594de2bba804bd | 5c8e4e590249a630a16b10bd7a77b27600fffbea367a0b585a920dd877e5471b | c1ccc(N2CCOCC2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[N;D1;H2:5]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 79 | [{"value": 79.0, "product": "N1(CCOCC1)C=1C=C(C=CC1)NN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.6, "product": "N1(CCOCC1)C=1C=C(C=CC1)NN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a cooled (−5 ° C.) solution of 3-morpholin-4-yl-phenylamine (44)(0.18 g, 1.00 mmol) in 2M HCl(aq) was added sodium nitrite (69 mg, 1.00 mmol in 1 ml water) dropwise. The red solution was stirred at −5° C. for 10 minutes before the addition of tin (II) chloride dihydrate (1.13 g, 5.0 mmol). The mixture was stirred vi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Hydrazine | null | null | c1ccccc1.C1COCC[NH]1 | Other | Cl | null | null | Nc1cccc(N2CCOCC2)c1>Cl>NNc1cccc(N2CCOCC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0c6491ea44794e49912abacafa2be741 | Brc1cnc[nH]1.Clc1ccnc(Cl)n1>>Clc1nccc(-n2cncc2Br)n1 | O.BrC1=CN=CN1.ClC1=NC=CC(=N1)Cl.C([O-])([O-])=O.[K+].[K+]>>BrC1=CN=CN1C1=NC(=NC=C1)Cl | [nH:7]1[cH:8][n:9][cH:10][c:11]1[Br:12].Cl[c:6]1[cH:5][cH:4][n:3][c:2]([Cl:1])[n:13]1>>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6](-[n:7]2[cH:8][n:9][cH:10][c:11]2[Br:12])[n:13]1 | Brc1cnc[nH]1.Clc1ccnc(Cl)n1 | Clc1nccc(-n2cncc2Br)n1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 81a8af274888a1ce46b4f04ec3197b36b645c7f7cffa568e09093d352b49a738 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1cc(-n2ccnc2)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1.[Br;D1;H0:8]-[c:9]1:[c:10]:[#7;a:11]:[c:12]:[nH;D2;+0:13]:1>>[Br;D1;H0:8]-[c:9]1:[c:10]:[#7;a:11]:[c:12]:[n;H0;D3;+0:13]:1-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1 | 23.1 | [{"value": 23.0, "product": "BrC1=CN=CN1C1=NC(=NC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.1, "product": "BrC1=CN=CN1C1=NC(=NC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | To a solution of 2,4-dichloropyrimidine (0.447 g, 3 mmol) in anhydrous DMF (4 ml) was added potassium carbonate (0.415 g, 3 mmol). The reaction mixture was cooled (0° C.) under an inert atmosphere before the addition of 5-bromo-1-H-imidazole (0.441 g, 3 mmol) as solution in DMF (2 ml). The reaction was then allowed to ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1cncnc1 | c1cncnc1.c1cnc[nH]1 | c1cncnc1.c1cnc[nH]1 | HCl | CN(C)C=O | 0 | null | Brc1cnc[nH]1.Clc1ccnc(Cl)n1>CN(C)C=O>Clc1nccc(-n2cncc2Br)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-be8d5621b00248a9b7e90579189f0cfc | Brc1cn(-c2ccnc(N3CCOCC3)n2)cn1.COc1cccc(OC)c1O>>COc1cc(-c2cncn2-c2ccnc(N3CCOCC3)n2)cc(OC)c1O | BrC=1N=CN(C1)C1=NC(=NC=C1)N1CCOCC1.P(=O)([O-])([O-])[O-].[K+].[K+].[K+].COC1=C(C(=CC=C1)OC)O.B(O)O>>COC1=C(C(=CC(=C1)C=1N(C=NC1)C1=NC(=NC=C1)N1CCOCC1)OC)O | Br[c:7]1[cH:6][n:10](-[c:11]2[cH:12][cH:13][n:14][c:15]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[n:22]2)[cH:9][n:8]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:23][c:24]([O:25][CH3:26])[c:27]1[OH:28]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][n:8][cH:9][n:10]2-[c:11]2[cH:12][cH:13][n:14][c:15]([N:16]3[CH2:17][CH2:18][O... | Brc1cn(-c2ccnc(N3CCOCC3)n2)cn1.COc1cccc(OC)c1O | COc1cc(-c2cncn2-c2ccnc(N3CCOCC3)n2)cc(OC)c1O | null | null | O1CCOCC1.CC(=O)N(C)C | C-C Coupling | OtherReaction | 844cf792ab0cafb4af67f56a88ace2747e0faf85e02268ca713b25f81e565048 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2cncn2-c2ccnc(N3CCOCC3)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4](-[c:5]:[#7;a:6]):[cH;D2;+0:7]:1.[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]>>[#7;a:6]:[c:5]-[#7;a:4]1:[c:3]:[#7;a:2]:[cH;D2;+0:1]:[c;H0;D3;+0:7]:1-[c;H0;D3;+0:10](:[c:9]:[c:8]):[c:11]:[c:12] | 96.3 | [{"value": 96.0, "product": "COC1=C(C(=CC(=C1)C=1N(C=NC1)C1=NC(=NC=C1)N1CCOCC1)OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.3, "product": "COC1=C(C(=CC(=C1)C=1N(C=NC1)C1=NC(=NC=C1)N1CCOCC1)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 170 | CELSIUS | null | null | To a solution of 4-[4-(4-Bromo-imidazol-1-yl)-pyrimidin-2-yl]-morpholine (0.20 g, 0.65 mmol) in anhydrous dioxane (6 ml) and anhydrous DMA (0.6 m) was added tripotassium phosphate (0.28 g, 1.3 mmol) and 2,6-dimethoxy-phenol-boronic acid (0.18 g, 0.91 mmol). The resultant mixture was degassed with sonication for 10 minu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1ccccc1 | c1ccccc1.c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1.c1cncnc1.C1COCC[NH]1 | HBr | O1CCOCC1.CC(=O)N(C)C | 170 | null | Brc1cn(-c2ccnc(N3CCOCC3)n2)cn1.COc1cccc(OC)c1O>O1CCOCC1.CC(=O)N(C)C>COc1cc(-c2cncn2-c2ccnc(N3CCOCC3)n2)cc(OC)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-23d22030808947108ec6affc16e99c24 | Brc1c[nH]cn1.Clc1ccnc(Cl)n1>>Clc1nccc(-n2cnc(Br)c2)n1 | O.BrC=1N=CNC1.ClC1=NC=CC(=N1)Cl.C([O-])([O-])=O.[K+].[K+]>>BrC=1N=CN(C1)C1=NC(=NC=C1)Cl | [nH:7]1[cH:8][n:9][c:10]([Br:11])[cH:12]1.Cl[c:6]1[cH:5][cH:4][n:3][c:2]([Cl:1])[n:13]1>>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6](-[n:7]2[cH:8][n:9][c:10]([Br:11])[cH:12]2)[n:13]1 | Brc1c[nH]cn1.Clc1ccnc(Cl)n1 | Clc1nccc(-n2cnc(Br)c2)n1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | e64c0bd3880a16dae8dbdce158f5a8057eade05f62dc3f1bd7056598cea48127 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1cc(-n2ccnc2)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:1.[Br;D1;H0:8]-[c:9]1:[#7;a:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1>>[Br;D1;H0:8]-[c:9]1:[#7;a:10]:[c:11]:[n;H0;D3;+0:12](-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6]:[c:7]:2):[c:13]:1 | 23.1 | [{"value": 23.0, "product": "BrC=1N=CN(C1)C1=NC(=NC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.1, "product": "BrC=1N=CN(C1)C1=NC(=NC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | To a solution of 2,4-dichloropyrimidine (0.447 g, 3 mmol) in anhydrous DMF (4 ml) was added potassium carbonate (0.415 g, 3 mmol). The reaction mixture was cooled (0° C.) under an inert atmosphere before the addition of 4-bromo-1-H-imidazole (0.441 g, 3 mmol) as solution in DMF (2 ml). The reaction was then allowed to ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1cncnc1 | c1cncnc1.c1c[nH]cn1 | c1cncnc1.c1c[nH]cn1 | HCl | CN(C)C=O | 0 | null | Brc1c[nH]cn1.Clc1ccnc(Cl)n1>CN(C)C=O>Clc1nccc(-n2cnc(Br)c2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c0d2761665384129aebcdcaf6ef4867a | C1COCCN1.Clc1nccc(-n2cnc(Br)c2)n1>>Brc1cn(-c2ccnc(N3CCOCC3)n2)cn1 | N1CCOCC1.[H-].[Na+].BrC=1N=CN(C1)C1=NC(=NC=C1)Cl>>BrC=1N=CN(C1)C1=NC(=NC=C1)N1CCOCC1 | [NH:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1.Cl[c:9]1[n:8][cH:7][cH:6][c:5](-[n:4]2[cH:3][c:2]([Br:1])[n:18][cH:17]2)[n:16]1>>[Br:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][n:8][c:9]([N:10]3[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[n:16]2)[cH:17][n:18]1 | C1COCCN1.Clc1nccc(-n2cnc(Br)c2)n1 | Brc1cn(-c2ccnc(N3CCOCC3)n2)cn1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | b6ba2533a469a91b7ece94b4a523fa9d9d9bc584236787b5a2be96cdf7a917fc | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cn(-c2ccnc(N3CCOCC3)n2)cn1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1):[#7;a:4]:[c:5] | null | [] | null | null | null | null | To a cooled (0° C.) solution of morpholine (0.256 g, 2.94 mmol) in anhydrouse DMF (5 ml) was added NaH (0.117 g, 2.94 mmol, 60% disp' in mineral oil). The mixture was stirred at this temperature for 30 minutes before the addition of 4-(4-Bromo-imidazol-1-yl)-2-chloro-pyrimidine (0.64 g, 2.45 mmol). The reaction vessel ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1cncnc1 | c1cncnc1.C1COCC[NH]1 | c1c[nH]cn1.c1cncnc1.C1COCC[NH]1 | HCl | CN(C)C=O | null | null | C1COCCN1.Clc1nccc(-n2cnc(Br)c2)n1>CN(C)C=O>Brc1cn(-c2ccnc(N3CCOCC3)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d23601701674257bc08c9e2665decdf | Brc1cn(-c2ccnc(N3CCOCC3)n2)cn1.COc1cccc(OC)c1O>>COc1cc(-c2cncn2-c2ccnc(N3CCOCC3)n2)cc(OC)c1O | BrC=1N=CN(C1)C1=NC(=NC=C1)N1CCOCC1.P(=O)([O-])([O-])[O-].[K+].[K+].[K+].COC1=C(C(=CC=C1)OC)O.B(O)O>>COC1=C(C(=CC(=C1)C=1N(C=NC1)C1=NC(=NC=C1)N1CCOCC1)OC)O | Br[c:7]1[cH:6][n:10](-[c:11]2[cH:12][cH:13][n:14][c:15]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[n:22]2)[cH:9][n:8]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:23][c:24]([O:25][CH3:26])[c:27]1[OH:28]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][n:8][cH:9][n:10]2-[c:11]2[cH:12][cH:13][n:14][c:15]([N:16]3[CH2:17][CH2:18][O... | Brc1cn(-c2ccnc(N3CCOCC3)n2)cn1.COc1cccc(OC)c1O | COc1cc(-c2cncn2-c2ccnc(N3CCOCC3)n2)cc(OC)c1O | null | null | O1CCOCC1.CC(=O)N(C)C | C-C Coupling | OtherReaction | 844cf792ab0cafb4af67f56a88ace2747e0faf85e02268ca713b25f81e565048 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(-c2cncn2-c2ccnc(N3CCOCC3)n2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4](-[c:5]:[#7;a:6]):[cH;D2;+0:7]:1.[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]>>[#7;a:6]:[c:5]-[#7;a:4]1:[c:3]:[#7;a:2]:[cH;D2;+0:1]:[c;H0;D3;+0:7]:1-[c;H0;D3;+0:10](:[c:9]:[c:8]):[c:11]:[c:12] | 96.3 | [{"value": 96.0, "product": "COC1=C(C(=CC(=C1)C=1N(C=NC1)C1=NC(=NC=C1)N1CCOCC1)OC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.3, "product": "COC1=C(C(=CC(=C1)C=1N(C=NC1)C1=NC(=NC=C1)N1CCOCC1)OC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 170 | CELSIUS | null | null | To a solution of 4-[4-(4-Bromo-imidazol-1-yl)-pyrimidin-2-yl]-morpholine (0.20 g, 0.65 mmol) in anhydrous dioxane (6 ml) and anhydrous DMA (0.6 m) was added tripotassium phosphate (0.28 g, 1.3 mmol) and 2,6-dimethoxy-phenol-boronic acid (0.18 g, 0.91 mmol). The resultant mixture was degassed with sonication for 10 minu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1ccccc1 | c1ccccc1.c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1.c1cncnc1.C1COCC[NH]1 | HBr | O1CCOCC1.CC(=O)N(C)C | 170 | null | Brc1cn(-c2ccnc(N3CCOCC3)n2)cn1.COc1cccc(OC)c1O>O1CCOCC1.CC(=O)N(C)C>COc1cc(-c2cncn2-c2ccnc(N3CCOCC3)n2)cc(OC)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d16f1292e8045c985187f9ef64767a9 | Brc1csc(Br)n1.Clc1ncccn1>>Clc1nccc(-c2nc(Br)cs2)n1 | ClC1=NC=CC=N1.C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N.O.[OH-].[Na+].C(CCC)[Li].BrC=1SC=C(N1)Br>>BrC=1N=C(SC1)C1=NC(=NC=C1)Cl | Br[c:7]1[n:8][c:9]([Br:10])[cH:11][s:12]1.[Cl:1][c:2]1[n:3][cH:4][cH:5][cH:6][n:13]1>>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]([Br:10])[cH:11][s:12]2)[n:13]1 | Brc1csc(Br)n1.Clc1ncccn1 | Clc1nccc(-c2nc(Br)cs2)n1 | null | null | C(C)OCC.C1CCOC1 | C-C Coupling | OtherReaction | 981234079ebe4a72c4e2d22c2b43a445582326b46269b83374518510b146a29a | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1cc(-c2nccs2)ncn1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[Cl;D1;H0:6]-[c:7]1:[#7;a:8]:[cH;D2;+0:9]:[c:10]:[c:11]:[#7;a:12]:1>>[Cl;D1;H0:6]-[c:7]1:[#7;a:8]:[c;H0;D3;+0:9](-[c;H0;D3;+0:1]2:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:2):[c:10]:[c:11]:[#7;a:12]:1 | 99.8 | [{"value": 47.1, "product": "BrC=1N=C(SC1)C1=NC(=NC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.8, "product": "BrC=1N=C(SC1)C1=NC(=NC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a cooled (−78° C.) solution of 2,4-dibromothiazole (1.22 g, 5.0 mmol) in anhydrous diethyl ether (15 ml) was added n-Butyllithium (2.2 ml of 2.5 M solution in Hexanes, 5.5 mmol) in a dropwise fashion. The mixture was maintained at this temperature, with stirring, for 1 hour before a suspension of 2-chloropyrimidine ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cscn1.c1cncnc1 | c1cncnc1.c1cscn1 | c1cncnc1.c1cscn1 | HBr | C(C)OCC.C1CCOC1 | null | 1 | Brc1csc(Br)n1.Clc1ncccn1>C(C)OCC.C1CCOC1>Clc1nccc(-c2nc(Br)cs2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e63c85de40f042aaa9cf7b7f8d4fbffa | Brc1ccc(Br)o1.Clc1ncccn1>>Clc1nccc(-c2ccc(Br)o2)n1 | C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N.C(CCC)[Li].BrC=1OC(=CC1)Br.ClC1=NC=CC=N1>>BrC1=CC=C(O1)C1=NC(=NC=C1)Cl | Br[c:7]1[cH:8][cH:9][c:10]([Br:11])[o:12]1.[Cl:1][c:2]1[n:3][cH:4][cH:5][cH:6][n:13]1>>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Br:11])[o:12]2)[n:13]1 | Brc1ccc(Br)o1.Clc1ncccn1 | Clc1nccc(-c2ccc(Br)o2)n1 | null | null | CCOC(=O)C.C(C)OCC | C-C Coupling | OtherReaction | 1fb7301aeb37f7dce6f960069599ea4d881dea7dd95f059016b7a162ac28edb9 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1coc(-c2ccncn2)c1 | Br-[c;H0;D3;+0:1]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1.[Cl;D1;H0:6]-[c:7]1:[#7;a:8]:[cH;D2;+0:9]:[c:10]:[c:11]:[#7;a:12]:1>>[Cl;D1;H0:6]-[c:7]1:[#7;a:8]:[c;H0;D3;+0:9](-[c;H0;D3;+0:1]2:[#8;a:2]:[c:3]:[c:4]:[c:5]:2):[c:10]:[c:11]:[#7;a:12]:1 | 40.2 | [{"value": 40.2, "product": "BrC1=CC=C(O1)C1=NC(=NC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a cooled (−78° C.) solution of 2,5-dibromofurane (3.06 g, 8.88 mmol) in anhydrous diethyl ether (50 ml) was added n-Butyllithium (3.9 ml of 2.5M solution in Hexanes, 9.77 mmol). The mixture was stirred at this temperature for 90 minutes before the addition of 2-chloropyrimidine. The mixture was stirred for a further... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccoc1.c1cncnc1 | c1cncnc1.c1ccoc1 | c1cncnc1.c1ccoc1 | HBr | CCOC(=O)C.C(C)OCC | null | 0.5 | Brc1ccc(Br)o1.Clc1ncccn1>CCOC(=O)C.C(C)OCC>Clc1nccc(-c2ccc(Br)o2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-95a3cc50a6fa4d84a89131d02674c994 | Clc1cc(Cl)nc(Cl)n1.OB(O)c1ccco1>>Clc1cc(-c2ccco2)nc(Cl)n1 | ClC1=NC(=CC(=N1)Cl)Cl.O1C(=CC=C1)B(O)O.C([O-])([O-])=O.[K+].[K+]>>ClC1=NC(=CC(=N1)Cl)C=1OC=CC1 | Cl[c:4]1[cH:3][c:2]([Cl:1])[n:13][c:11]([Cl:12])[n:10]1.OB(O)[c:5]1[cH:6][cH:7][cH:8][o:9]1>>[Cl:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[n:10][c:11]([Cl:12])[n:13]1 | Clc1cc(Cl)nc(Cl)n1.OB(O)c1ccco1 | Clc1cc(-c2ccco2)nc(Cl)n1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | 10a97fb451331038632d4eab00d75ba2fa56f845cd92b47922f288fa162ae29c | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1coc(-c2ccncn2)c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1.O-B(-O)-[c;H0;D3;+0:9]1:[#8;a:10]:[c:11]:[c:12]:[c:13]:1>>[Cl;D1;H0:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9]2:[#8;a:10]:[c:11]:[c:12]:[c:13]:2):[c:8]:[c:6](-[Cl;D1;H0:7]):[#7;a:5]:1 | 116.9 | [{"value": 58.0, "product": "ClC1=NC(=CC(=N1)Cl)C=1OC=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 116.9, "product": "ClC1=NC(=CC(=N1)Cl)C=1OC=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | null | null | To a solution of 2,4,6-trichloropyrimidine (0.5 g, 2.73 mmol), 2-furanboronic acid (0.152 g, 1.36 mmol), potassium carbonate (0.377 g, 1.36 mmol)) in toluene (2.5 ml) was added tetrakis(triphenylphosphine)palladium (0.08 g, 0.068 mmol). The reaction vessel was sealed and heated under the influence of microwave radiatio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cncnc1.c1ccoc1 | c1cncnc1.c1ccoc1 | c1cncnc1.c1ccoc1 | HCl.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C | 130 | null | Clc1cc(Cl)nc(Cl)n1.OB(O)c1ccco1>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.C1(=CC=CC=C1)C>Clc1cc(-c2ccco2)nc(Cl)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aad6a35505cf413f8f81442d8ac5ff79 | Clc1cc(-c2ccco2)nc(Cl)n1.O=C1CCC(=O)N1Br>>Clc1cc(-c2ccc(Br)o2)nc(Cl)n1 | ClC1=NC(=CC(=N1)Cl)C=1OC=CC1.BrN1C(CCC1=O)=O>>BrC1=CC=C(O1)C1=NC(=NC(=C1)Cl)Cl | [Cl:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:10]2)[n:11][c:12]([Cl:13])[n:14]1.O=C1CCC(=O)N1[Br:9]>>[Cl:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([Br:9])[o:10]2)[n:11][c:12]([Cl:13])[n:14]1 | Clc1cc(-c2ccco2)nc(Cl)n1.O=C1CCC(=O)N1Br | Clc1cc(-c2ccc(Br)o2)nc(Cl)n1 | null | null | CN(C)C=O.CCOC(=O)C | Functional Group Interconversion | Bromination | c5c258c367f40c41fade67fa4750fbbb47b73b9a02d390d11e4f14dcb8424f93 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1coc(-c2ccncn2)c1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8;a:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:6]1:[#8;a:2]:[c:3]:[c:4]:[c:5]:1 | 99 | [{"value": 99.0, "product": "BrC1=CC=C(O1)C1=NC(=NC(=C1)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.4, "product": "BrC1=CC=C(O1)C1=NC(=NC(=C1)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of 2,4-Dichloro-6-furan-2-yl-pyrimidine (1.44 g, 6.71 mmol) in DMF (20 ml) was added N-bromosuccinimide (1.31 g, 7.38 mmol) in a portionwise fashion. The resultant mixture was stirred at room temperature for a 2.5 hours before being diluted in EtOAc (50 ml) and washed with water (2×50 ml). The org... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1ccoc1.C1CCNC1 | c1ccoc1 | c1cncnc1.c1ccoc1 | HO- | CN(C)C=O.CCOC(=O)C | null | null | Clc1cc(-c2ccco2)nc(Cl)n1.O=C1CCC(=O)N1Br>CN(C)C=O.CCOC(=O)C>Clc1cc(-c2ccc(Br)o2)nc(Cl)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dc280072dcda42c8ba814fb64f18c298 | C1COCCN1.CC(=O)N(C)C.CCN(C(C)C)C(C)C.Clc1cc(-c2ccc(Br)o2)nc(Cl)n1>>Brc1ccc(-c2cc(N3CCOCC3)nc(N3CCOCC3)n2)o1 | BrC1=CC=C(O1)C1=NC(=NC(=C1)Cl)Cl.N1CCOCC1.C(C)(C)N(C(C)C)CC.CC(=O)N(C)C>>BrC1=CC=C(O1)C1=NC(=NC(=C1)N1CCOCC1)N1CCOCC1 | [NH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1.CN(C)[C:19]([CH3:18])=[O:20].CC(C)[N:17](C(C)C)[CH2:22][CH3:21].Cl[c:8]1[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([Br:1])[o:24]2)[n:23][c:16](Cl)[n:15]1>>[Br:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([N:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)[n:15][c:16]([N:17]3[CH2:18][... | C1COCCN1.CC(=O)N(C)C.CCN(C(C)C)C(C)C.Clc1cc(-c2ccc(Br)o2)nc(Cl)n1 | Brc1ccc(-c2cc(N3CCOCC3)nc(N3CCOCC3)n2)o1 | null | null | CCOC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | d54716cbc115463dd993d711c8d100d4f9bb1277362ee3167798bf396caabc59 | 1c6534aa4d9bf765fffd0f91b65bac4b9aba2e23419e954057bef99f64a5391e | c1coc(-c2cc(N3CCOCC3)nc(N3CCOCC3)n2)c1 | C-C(-C)-[N;H0;D3;+0:1](-[C:2]-[CH3;D1;+0:3])-C(-C)-C.C-N(-C)-[C;H0;D3;+0:4](-[CH3;D1;+0:5])=[O;H0;D1;+0:6].Cl-[c;H0;D3;+0:7]1:[#7;a:8]:[c;H0;D3;+0:9](-Cl):[c:10]:[c:11](-[c:12]:[#8;a:13]):[#7;a:14]:1.[#8:15]1-[C:16]-[C:17]-[NH;D2;+0:18]-[C:19]-[C:20]-1>>[#8;a:13]:[c:12]-[c:11]1:[#7;a:14]:[c;H0;D3;+0:7](-[N;H0;D3;+0:1]2... | 37 | [{"value": 37.0, "product": "BrC1=CC=C(O1)C1=NC(=NC(=C1)N1CCOCC1)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | To a solution of 4-(5-Bromo-furan-2-yl)-2,6-dichloro-pyrimidine (1.93 g, 6.51 mmol) in DMA (35 ml) was added morpholine (2.83 g, 32.54 mmol) and N,N-diisopropylethylamine (4.21 g, 32.54 mmol). The reaction mixture was heated to 70° C. for 7 hours whereupon it was cooled and diluted with EtOAc (100 ml) and then washed w... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Tertiary amide.Secondary amine.Tertiary amine | Ether.Tertiary amine.Tertiary amine | C1COCCN1.c1cncnc1 | c1cncnc1.C1COCC[NH]1.C1COCC[NH]1 | c1ccoc1.c1cncnc1.C1COCC[NH]1.C1COCC[NH]1 | HCl | CCOC(=O)C | 70 | null | C1COCCN1.CC(=O)N(C)C.CCN(C(C)C)C(C)C.Clc1cc(-c2ccc(Br)o2)nc(Cl)n1>CCOC(=O)C>Brc1ccc(-c2cc(N3CCOCC3)nc(N3CCOCC3)n2)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-29590f2670a04d1d8482a49543b7c71c | Brc1csc(Br)c1.Clc1ncccn1>>Clc1nccc(-c2cc(Br)cs2)n1 | C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N.C(CCC)[Li].BrC=1SC=C(C1)Br.ClC1=NC=CC=N1>>BrC=1C=C(SC1)C1=NC(=NC=C1)Cl | Br[c:7]1[cH:8][c:9]([Br:10])[cH:11][s:12]1.[Cl:1][c:2]1[n:3][cH:4][cH:5][cH:6][n:13]1>>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([Br:10])[cH:11][s:12]2)[n:13]1 | Brc1csc(Br)c1.Clc1ncccn1 | Clc1nccc(-c2cc(Br)cs2)n1 | null | null | C(C)(=O)OCC.C(C)OCC | C-C Coupling | OtherReaction | e1672f5ac493608b92118561b5b7f9997b63eb7c75246f69153be7152d9c7116 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1csc(-c2ccncn2)c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1.[Cl;D1;H0:6]-[c:7]1:[#7;a:8]:[cH;D2;+0:9]:[c:10]:[c:11]:[#7;a:12]:1>>[Cl;D1;H0:6]-[c:7]1:[#7;a:8]:[c;H0;D3;+0:9](-[c;H0;D3;+0:1]2:[#16;a:2]:[c:3]:[c:4]:[c:5]:2):[c:10]:[c:11]:[#7;a:12]:1 | 37 | [{"value": 37.0, "product": "BrC=1C=C(SC1)C1=NC(=NC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.9, "product": "BrC=1C=C(SC1)C1=NC(=NC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 30 | MINUTE | To a cooled (−78° C.) solution of 2,4-dibromothiophene (1 g, 4.13 mmol) in diethylether (30 ml) was added n-butyl lithium (2.5M in Hexanes, 4.55 mmol, 1.82 ml). The solution was maintained at this temperature for 1 hour before the addition of 2-chloropyrimidine (0.47 g, 4.13 mmol) in a single portion. The mixture was m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccsc1.c1cncnc1 | c1cncnc1.c1ccsc1 | c1cncnc1.c1ccsc1 | HBr | C(C)(=O)OCC.C(C)OCC | -78 | 0.5 | Brc1csc(Br)c1.Clc1ncccn1>C(C)(=O)OCC.C(C)OCC>Clc1nccc(-c2cc(Br)cs2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-56bb0cc15b044135b014d59f604e9693 | N#C[O-].Nc1ncccc1C(=O)O>>O=c1[nH]c(=O)c2cccnc2[nH]1 | NC1=C(C(=O)O)C=CC=N1.[Cl-].[NH4+].[O-]C#N.[K+]>>N1C(NC(C2=C1N=CC=C2)=O)=O | [O-:1][C:2]#[N:3].O[C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][n:10][c:11]1[NH2:12]>>[O:1]=[c:2]1[nH:3][c:4](=[O:5])[c:6]2[cH:7][cH:8][cH:9][n:10][c:11]2[nH:12]1 | N#C[O-].Nc1ncccc1C(=O)O | O=c1[nH]c(=O)c2cccnc2[nH]1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | c51f92ee998da8f6b25554f55d0c43da6abaff755f2e7598893294a09702c944 | c1ccf57c04ae079aa280df336a40d2004200703e7d31e551c16551a0131a704d | O=c1[nH]c(=O)c2cccnc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[#7;a:7]:[c:8].[N;H0;D1;+0:9]#[C;H0;D2;+0:10]-[O-;H0;D1:11]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:9]:[c;H0;D3;+0:10](=[O;H0;D1;+0:11]):[nH;D2;+0:6]:[c:5](:[#7;a:7]:[c:8]):[c:3]:1:[c:4] | 99.7 | [{"value": 99.0, "product": "N1C(NC(C2=C1N=CC=C2)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "N1C(NC(C2=C1N=CC=C2)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 200 | CELSIUS | 30 | MINUTE | A slurry of 2-aminonicotinic acid (10 g, 72.5 mmol), ammonium chloride (39 g, 725 mmol) and potassium cyanate (30 g, 362 mmol) in water (80 ml) was heated to 80° C. and maintained at this temperature with stirring for 30 minutes before being heated to 200° C. The mixture was stirred for 2 hours at this elevated tempera... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Nitrile.Primary amine | null | c1ccncc1 | c1ncc2cccnc2n1 | c1ncc2cccnc2n1 | HO- | O | 200 | 0.5 | N#C[O-].Nc1ncccc1C(=O)O>O>O=c1[nH]c(=O)c2cccnc2[nH]1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7c3d95e326b64e739752398e1f3b3878 | O=C(N1CCc2ccccc2CC1)C(F)(F)F.O=S(=O)(O)Cl>>O=C(N1CCc2ccc(S(=O)(=O)Cl)cc2CC1)C(F)(F)F | FC(C(=O)N1CCC2=C(CC1)C=CC=C2)(F)F.ClS(=O)(=O)O>>FC(C(=O)N1CCC2=C(CC1)C=CC(=C2)S(=O)(=O)Cl)(F)F | [O:1]=[C:2]([N:3]1[CH2:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:14][c:15]2[CH2:16][CH2:17]1)[C:18]([F:19])([F:20])[F:21].O=[S:10]([OH:11])(=[O:12])[Cl:13]>>[O:1]=[C:2]([N:3]1[CH2:4][CH2:5][c:6]2[cH:7][cH:8][c:9]([S:10](=[O:11])(=[O:12])[Cl:13])[cH:14][c:15]2[CH2:16][CH2:17]1)[C:18]([F:19])([F:20])[F:21] | O=C(N1CCc2ccccc2CC1)C(F)(F)F.O=S(=O)(O)Cl | O=C(N1CCc2ccc(S(=O)(=O)Cl)cc2CC1)C(F)(F)F | null | null | ClCCl | Protection | Aromatic sulfonyl chlorination | e214876e01ef40d6d966c37fa1c9cb6bd5a3863e25c8e1628e980007a763d16a | c731d053565135be022f3edbe36cf28a9b4364ca579bdb183b2db9578bab4695 | c1ccc2c(c1)CCNCC2 | O=[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])-[OH;D1;+0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;H0;D1;+0:4])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | 84.1 | [{"value": 84.1, "product": "FC(C(=O)N1CCC2=C(CC1)C=CC(=C2)S(=O)(=O)Cl)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of 3-trifluoroacetyl-2,3,4,5-tetrahydro-1H-3-benzazepine (see WO02/40471) (20 g, 80 mmol) in dichloromethane (50 mL) was added dropwise to a solution of chlorosulfonic acid (33 mL, 240 mmol) in more dichloromethane (200 mL) at 0° C. The resulting solution was stirred for 18 h without cooling then poured onto... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccc2c(c1)CC[NH]CC2 | c1ccc2c(c1)CC[NH]CC2 | c1ccc2c(c1)CC[NH]CC2 | HO- | ClCCl | null | 18 | O=C(N1CCc2ccccc2CC1)C(F)(F)F.O=S(=O)(O)Cl>ClCCl>O=C(N1CCc2ccc(S(=O)(=O)Cl)cc2CC1)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d21019d42db04134bf3db7424f83b87b | O=C(N1CCc2ccc(S(=O)(=O)Cl)cc2CC1)C(F)(F)F.[F-]>>O=C(N1CCc2ccc(S(=O)(=O)F)cc2CC1)C(F)(F)F | FC(C(=O)N1CCC2=C(CC1)C=CC(=C2)S(=O)(=O)Cl)(F)F.[F-].[K+].C(C)#N.O>>FC(C(=O)N1CCC2=C(CC1)C=CC(=C2)S(=O)(=O)F)(F)F | Cl[S:10]([c:9]1[cH:8][cH:7][c:6]2[c:15]([cH:14]1)[CH2:16][CH2:17][N:3]([C:2](=[O:1])[C:18]([F:19])([F:20])[F:21])[CH2:4][CH2:5]2)(=[O:11])=[O:12].[F-:13]>>[O:1]=[C:2]([N:3]1[CH2:4][CH2:5][c:6]2[cH:7][cH:8][c:9]([S:10](=[O:11])(=[O:12])[F:13])[cH:14][c:15]2[CH2:16][CH2:17]1)[C:18]([F:19])([F:20])[F:21] | O=C(N1CCc2ccc(S(=O)(=O)Cl)cc2CC1)C(F)(F)F.[F-] | O=C(N1CCc2ccc(S(=O)(=O)F)cc2CC1)C(F)(F)F | null | C1COCCOCCOCCOCCOCCO1 | C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | 1a5adee7f1ba8844d3aeea23793c6ed559c5770364925cb0ebd2c7a72ae17659 | 100ecb262b71c25deadc3940d6f3c2c0e7443b2546e5e1649d38d873195b4540 | c1ccc2c(c1)CCNCC2 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[F-;H0;D0:7]>>[F;H0;D1;+0:7]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 96.4 | [{"value": 96.4, "product": "FC(C(=O)N1CCC2=C(CC1)C=CC(=C2)S(=O)(=O)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 3-trifluoroacetyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7-sulfonyl chloride (23 g, 67 mmol), potassium fluoride (12 g, 200 mmol), 18-crown-6 (0.1 g), and acetonitrile (100 mL) was stirred overnight. Water (200 mL) and ethyl acetate (200 mL) were added and the organic layer was washed with brine (100 mL), dri... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | Sulfonyl halide | null | null | c1ccc2c(c1)CC[NH]CC2 | Other | C1COCCOCCOCCOCCOCCO1.C(C)(=O)OCC | null | 8 | O=C(N1CCc2ccc(S(=O)(=O)Cl)cc2CC1)C(F)(F)F.[F-]>C1COCCOCCOCCOCCOCCO1.C(C)(=O)OCC>O=C(N1CCc2ccc(S(=O)(=O)F)cc2CC1)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cfc0c3931452434e99dfef546e8575c2 | CC(C)(C)[Si](C)(C)Oc1cccc(Br)c1.O=C(N1CCc2ccc(S(=O)(=O)F)cc2CC1)C(F)(F)F>>CC(C)(C)[Si](C)(C)Oc1cccc(S(=O)(=O)c2ccc3c(c2)CCNCC3)c1 | FC(C(=O)N1CCC2=C(CC1)C=CC(=C2)S(=O)(=O)F)(F)F.[Si](C)(C)(C(C)(C)C)OC=1C=C(C=CC1)Br>>[Si](C)(C)(C(C)(C)C)OC=1C=C(C=CC1)S(=O)(=O)C1=CC2=C(CCNCC2)C=C1 | Br[c:13]1[cH:12][cH:11][cH:10][c:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[cH:28]1.O=C(C(F)(F)F)[N:25]1[CH2:24][CH2:23][c:21]2[c:20]([cH:19][cH:18][c:17]([S:14](F)(=[O:15])=[O:16])[cH:22]2)[CH2:27][CH2:26]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][c:9]1[cH:10][cH:11][cH:12][c:1... | CC(C)(C)[Si](C)(C)Oc1cccc(Br)c1.O=C(N1CCc2ccc(S(=O)(=O)F)cc2CC1)C(F)(F)F | CC(C)(C)[Si](C)(C)Oc1cccc(S(=O)(=O)c2ccc3c(c2)CCNCC3)c1 | null | null | null | Acylation | OtherReaction | 6193e5d632721178f9656fae9abea83329af35cc8f87fd550cf95b1e426558c8 | 2755a1c28492a748a54f12bcb171010f717ae8b51f9d9bd8090d67ab0d82aefa | O=S(=O)(c1ccccc1)c1ccc2c(c1)CCNCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].F-C(-F)(-F)-C(=O)-[N;H0;D3;+0:6](-[C:7]-[C:8])-[C:9]-[C:10].F-[S;H0;D4;+0:11](=[O;D1;H0:12])(=[O;D1;H0:13])-[c:14](:[c:15]):[c:16]>>[C:8]-[C:7]-[NH;D2;+0:6]-[C:9]-[C:10].[O;D1;H0:12]=[S;H0;D4;+0:11](=[O;D1;H0:13])(-[c:14](:[c:15]):[c:16])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c... | 80 | [{"value": 80.0, "product": "[Si](C)(C)(C(C)(C)C)OC=1C=C(C=CC1)S(=O)(=O)C1=CC2=C(CCNCC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared from 3-trifluoroacetyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7-sulfonyl fluoride and 3-t-butyldimethylsilyloxybromobenzene using the method of Example 1, yield 80%.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Tertiary amide.Sulfonyl halide | Secondary amine.Sulfone | c1ccccc1.c1ccc2c(c1)CC[NH]CC2 | c1ccccc1.c1ccc2c(c1)CCNCC2 | c1ccccc1.c1ccc2c(c1)CCNCC2 | Br- | null | null | null | CC(C)(C)[Si](C)(C)Oc1cccc(Br)c1.O=C(N1CCc2ccc(S(=O)(=O)F)cc2CC1)C(F)(F)F>>CC(C)(C)[Si](C)(C)Oc1cccc(S(=O)(=O)c2ccc3c(c2)CCNCC3)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-01757e51bf184b71beac0e80b6269a70 | CC(C)(C)OC(=O)N1CCc2ccc(S(=O)(=O)c3cccc(O[Si](C)(C)C(C)(C)C)c3)cc2CC1>>CC(C)(C)OC(=O)N1CCc2ccc(S(=O)(=O)c3cccc(O)c3)cc2CC1 | [Si](C)(C)(C(C)(C)C)OC=1C=C(C=CC1)S(=O)(=O)C1=CC2=C(CCN(CC2)C(=O)OC(C)(C)C)C=C1.O1CCCC1>>OC=1C=C(C=CC1)S(=O)(=O)C1=CC2=C(CCN(CC2)C(=O)OC(C)(C)C)C=C1 | CC(C)(C)[Si](C)(C)[O:23][c:22]1[cH:21][cH:20][cH:19][c:18]([S:15]([c:14]2[cH:13][cH:12][c:11]3[c:26]([cH:25]2)[CH2:27][CH2:28][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]3)(=[O:16])=[O:17])[cH:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14... | CC(C)(C)OC(=O)N1CCc2ccc(S(=O)(=O)c3cccc(O[Si](C)(C)C(C)(C)C)c3)cc2CC1 | CC(C)(C)OC(=O)N1CCc2ccc(S(=O)(=O)c3cccc(O)c3)cc2CC1 | null | null | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)OCC | Deprotection | Alcohol deprotection from silyl ethers | e70131badc7d7d580ed75b2dfb3ce6df2a5f496b2119611cf5354e1267babe73 | b09ece7bccc3ff762f4ff5407ad846fffba6d6a63735853c86a86d29904f54ed | O=S(=O)(c1ccccc1)c1ccc2c(c1)CCNCC2 | C-C(-C)(-C)-[Si](-C)(-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 | 1 | HOUR | 7-(3-t-Butyldimethysilyloxyphenylsulfonyl)-3-(t-butoxycarbonyl)-2,3,4,5-tetrahydro-1H-3-benzazepine (5.4 g, 10.5 mmol) was dissolved in a solution of tetra-n-butylammonium fluoride in tetrahydrofuran (15 mL, 1M, 15 mmol). The solution was stirred for 1 h then diluted with ethyl acetate (100 mL) and washed with saturate... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Aromatic alcohol | null | null | c1ccc2c(c1)CC[NH]CC2.c1ccccc1 | Other | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)OCC | null | 1 | CC(C)(C)OC(=O)N1CCc2ccc(S(=O)(=O)c3cccc(O[Si](C)(C)C(C)(C)C)c3)cc2CC1>[F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)OCC>CC(C)(C)OC(=O)N1CCc2ccc(S(=O)(=O)c3cccc(O)c3)cc2CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ba525f7bc4c7428ab27e6c146b106aa0 | C=O.COc1ccc2c(c1)CCNCC2>>COc1ccc2c(c1)CCN(C)CC2 | [OH-].[Na+].Cl.COC1=CC2=C(CCNCC2)C=C1.C=O.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>COC1=CC2=C(CCN(CC2)C)C=C1 | O=[CH2:12].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][NH:11][CH2:13][CH2:14]2>>[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]([CH3:12])[CH2:13][CH2:14]2 | C=O.COc1ccc2c(c1)CCNCC2 | COc1ccc2c(c1)CCN(C)CC2 | null | null | ClC(C)Cl.O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | 8d9cad772a98a414ce55384bd0cd4b440b5a4763409ac2b73eace6e178c9f3d7 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc2c(c1)CCNCC2 | O=[CH2;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[C:5]-[C:6] | 96.2 | [{"value": 96.2, "product": "COC1=CC2=C(CCN(CC2)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride (see EP 285287) (25 g, 125 mmol) and 37% formalin (25 mL) in dichloroethane (250 mL) was treated with sodium triacetoxyborohydride (30 g, 250 mmol) keeping the internal temperature below 20° C. After stirring for 2 h, water was added and the pH ad... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | c1ccc2c(c1)CCNCC2 | c1ccc2c(c1)CC[NH]CC2 | c1ccc2c(c1)CC[NH]CC2 | Other | ClC(C)Cl.O | null | 2 | C=O.COc1ccc2c(c1)CCNCC2>ClC(C)Cl.O>COc1ccc2c(c1)CCN(C)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b6ab01f798244e8b1487d9e6a44336f | COc1cc2c(cc1S(=O)(=O)F)CCN(C)CC2.Fc1cc[c]([Mg][Br])cc1>>COc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CCN(C)CC2 | O.O.O.O.C(=O)([O-])C(O)C(O)C(=O)[O-].[K+].[Na+].COC=1C(=CC2=C(CCN(CC2)C)C1)S(=O)(=O)F.O1CCCC1.FC1=CC=C(C=C1)[Mg]Br.O1CCCC1>>FC1=CC=C(C=C1)S(=O)(=O)C1=CC2=C(CCN(CC2)C)C=C1OC | F[S:9]([c:8]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([cH:7]1)[CH2:19][CH2:20][N:21]([CH3:22])[CH2:23][CH2:24]2)(=[O:10])=[O:11].[Br][Mg][c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1)[CH2:19][CH2:... | COc1cc2c(cc1S(=O)(=O)F)CCN(C)CC2.Fc1cc[c]([Mg][Br])cc1 | COc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CCN(C)CC2 | null | null | O.C(C)OCC | Acylation | OtherReaction | d3a1550ec4795e48cc883187edc9f1cd54940ff6c6a62bb29abb4ea513e92466 | 6c968a334f06fdfd129db7d45220d1f2fdc6c99d2a47f19e8815cbc66b1933fc | O=S(=O)(c1ccccc1)c1ccc2c(c1)CCNCC2 | F-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[Br]-[Mg]-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11] | 51 | [{"value": 51.0, "product": "FC1=CC=C(C=C1)S(=O)(=O)C1=CC2=C(CCN(CC2)C)C=C1OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | The sulfonyl fluoride D4 from Description 4 (25 g) was dissolved it dry tetrahydrofuran (250 mL) and 4-fluorophenylmagnesium bromide in tetrahydrofuran (2.5 equivalents) added over 15 min with ice bath cooling, an exotherm only apparent during the first part of the addition. Stirred overnight without cooling then added... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Sulfonyl halide | Sulfone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)CC[NH]CC2 | Br-.Mg | O.C(C)OCC | null | 8 | COc1cc2c(cc1S(=O)(=O)F)CCN(C)CC2.Fc1cc[c]([Mg][Br])cc1>O.C(C)OCC>COc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CCN(C)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4f8d102d083941a48b12fa9e1bf0b32b | COc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CCN(C)CC2>>CN1CCc2cc(O)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1 | FC1=CC=C(C=C1)S(=O)(=O)C1=CC2=C(CCN(CC2)C)C=C1OC.Br>>Br.FC1=CC=C(C=C1)S(=O)(=O)C=1C(=CC2=C(CCN(CC2)C)C1)O | C[O:9][c:8]1[cH:7][c:6]2[c:22]([cH:21][c:10]1[S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1)[CH2:23][CH2:24][N:3]([CH3:2])[CH2:4][CH2:5]2>>[CH3:2][N:3]1[CH2:4][CH2:5][c:6]2[cH:7][c:8]([OH:9])[c:10]([S:11](=[O:12])(=[O:13])[c:14]3[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]3)[cH:21][c:22]2[CH2:... | COc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CCN(C)CC2 | CN1CCc2cc(O)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=S(=O)(c1ccccc1)c1ccc2c(c1)CCNCC2 | 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 | A solution of D5 (300 mg, 0.86 mmol) in aqueous 48% HBr (10 mL) was heated at 120° C. overnight. The mixture was cooled to room temperature and the solvent removed, azeotroping with toluene. Diethyl ether was added to the residue to yield the title compound D6 as the hydrobromide salt (340 mg). MH+ 336. 1H NMR δ (DMSO-... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2c(c1)CC[NH]CC2.c1ccccc1 | Other | null | null | null | COc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CCN(C)CC2>>CN1CCc2cc(O)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-14a3949cfc4c4aacbddb66084abdf429 | CN1CCc2cc(O)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1.O=S(=O)(Cl)C(F)(F)F>>CN1CCc2cc(OS(=O)(=O)C(F)(F)F)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1 | Br.FC1=CC=C(C=C1)S(=O)(=O)C=1C(=CC2=C(CCN(CC2)C)C1)O.C(C)N(CC)CC.FC(S(=O)(=O)Cl)(F)F>>FC1=CC=C(C=C1)S(=O)(=O)C=1C(=CC2=C(CCN(CC2)C)C1)OS(=O)(=O)C(F)(F)F | [CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([OH:8])[c:16]([S:17](=[O:18])(=[O:19])[c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[cH:27][c:28]2[CH2:29][CH2:30]1.Cl[S:9](=[O:10])(=[O:11])[C:12]([F:13])([F:14])[F:15]>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([O:8][S:9](=[O:10])(=[O:11])[C:12]([F:13])([F:14])[F:1... | CN1CCc2cc(O)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1.O=S(=O)(Cl)C(F)(F)F | CN1CCc2cc(OS(=O)(=O)C(F)(F)F)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1 | null | null | CC(=O)C | Acylation | Formation of Sulfonic Esters | e49e8a89829d16e9baa8e4b4ff3af6cddf2c699437b103af5529e9352ca19049 | c097f7b561618d6c43a42a968be5ff80232867be01d32b7e03ea7efb85610798 | O=S(=O)(c1ccccc1)c1ccc2c(c1)CCNCC2 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4](-[F;D1;H0:5])(-[F;D1;H0:6])-[F;D1;H0:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:5]-[C:4](-[F;D1;H0:6])(-[F;D1;H0:7])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 70.4 | [{"value": 70.4, "product": "FC1=CC=C(C=C1)S(=O)(=O)C=1C(=CC2=C(CCN(CC2)C)C1)OS(=O)(=O)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To an ice bath cooled solution of D6 (340 mg, 0.82 mmol) in acetone (10 mL) was added triethylamine (0.29 mL, 2.1 mmol) followed by trifluoromethanesulfonyl chloride (0.13 mL, 1.2 mmol). The mixture was stirred at room temperature for 2 hours. The solvent was removed and the residue partitioned between dichloromethane ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Sulfonyl halide | Triflate | null | null | c1ccc2c(c1)CC[NH]CC2.c1ccccc1 | HCl | CC(=O)C | null | 2 | CN1CCc2cc(O)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1.O=S(=O)(Cl)C(F)(F)F>CC(=O)C>CN1CCc2cc(OS(=O)(=O)C(F)(F)F)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-120cde5cc5424870be0ea4daed0c917b | CN1CCc2cc(OS(=O)(=O)C(F)(F)F)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1>>Cc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CCN(C)CC2 | FC1=CC=C(C=C1)S(=O)(=O)C=1C(=CC2=C(CCN(CC2)C)C1)OS(=O)(=O)C(F)(F)F.[Cl-].C[Zn+]>>FC1=CC=C(C=C1)S(=O)(=O)C1=CC2=C(CCN(CC2)C)C=C1C | O=S(=O)(O[c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1)[CH2:18][CH2:19][N:20]([CH3:21])[CH2:22][CH2:23]2)C(F)(F)F>>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][c:7]1[S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1)[CH2:18][CH2:19][N:20]([CH... | CN1CCc2cc(OS(=O)(=O)C(F)(F)F)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1 | Cc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CCN(C)CC2 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCCC1 | Functional Group Interconversion | OtherReaction | 6e78485b98f35b42fc34f259d94889f9ed985aa9e228eb426d445382d0da9c4a | b176f4ca0adee4f5ff077805596a10ddc6aa820843e17b6a0f5ce62bb8d509d7 | O=S(=O)(c1ccccc1)c1ccc2c(c1)CCNCC2 | F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#16:5]):[c:6]>>[#16:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C;D1;H3:7]):[c:2]:[c:3] | 80 | [{"value": 80.0, "product": "FC1=CC=C(C=C1)S(=O)(=O)C1=CC2=C(CCN(CC2)C)C=C1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of D7 (100 mg, 0.21 mmol) in dry tetrahydrofuran (2 mL) was degassed with argon for 10 minutes. To the solution Pd(PPh3)4 (30 mg) was added followed by methylzinc chloride (0.22 mL, 0.43 mmol) then heated at reflux for 30 minutes. The mixture was cooled to room temperature and quenched with water. Extraction... | 10.6084/m9.figshare.5104873.v1 | null | Triflate | null | c1ccc2c(c1)CC[NH]CC2 | c1ccc2c(c1)CC[NH]CC2 | c1ccccc1.c1ccc2c(c1)CC[NH]CC2 | Other | 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.O1CCCC1 | null | null | CN1CCc2cc(OS(=O)(=O)C(F)(F)F)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1>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.O1CCCC1>Cc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CCN(C)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d1982c7754cb4989a741bba95f1a126f | CCOC(OCC)c1ccc(Br)cc1.COc1cc2c(cc1S(=O)(=O)F)CCN(C)CC2>>COc1cc2c(cc1S(=O)(=O)c1ccc(C=O)cc1)CCN(C)CC2 | C(=O)([O-])C(O)C(O)C(=O)[O-].[Na+].[K+].[Mg].C(C)OC(C1=CC=C(C=C1)Br)OCC.COC=1C(=CC2=C(CCN(CC2)C)C1)S(=O)(=O)F>>COC=1C(=CC2=C(CCN(CC2)C)C1)S(=O)(=O)C1=CC=C(C=O)C=C1 | CCO[CH:16]([c:15]1[cH:14][cH:13][c:12](Br)[cH:19][cH:18]1)[O:17]CC.F[S:9]([c:8]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([cH:7]1)[CH2:20][CH2:21][N:22]([CH3:23])[CH2:24][CH2:25]2)(=[O:10])=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH:16]=[O:17])[cH:18][cH:19... | CCOC(OCC)c1ccc(Br)cc1.COc1cc2c(cc1S(=O)(=O)F)CCN(C)CC2 | COc1cc2c(cc1S(=O)(=O)c1ccc(C=O)cc1)CCN(C)CC2 | null | null | O1CCCC1.O | Acylation | OtherReaction | c33d00ab8fcb3501f6b71677ee349d83851a79b870a8bfc0576c30d1df9173b4 | 2feba15f740da3bc2af8b8458bdf8a7e30c69ff439b9e8f1fd30a71ff53b6010 | O=S(=O)(c1ccccc1)c1ccc2c(c1)CCNCC2 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[CH;D3;+0:5](-O-C-C)-[O;H0;D2;+0:6]-C-C):[c:7]:[c:8]:1.F-[S;H0;D4;+0:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12](:[c:13]):[c:14]>>[O;D1;H0:10]=[S;H0;D4;+0:9](=[O;D1;H0:11])(-[c:12](:[c:13]):[c:14])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](-[CH;D2;+0:5]=[O;H0;D1;+0:6]):[c:7]:[c:8]:1 | null | [] | null | null | 4 | HOUR | Magnesium turnings (1.4 g) in tetrahydrofuran (10 mL) were stirred under an atmosphere of argon and treated with a solution of 4-bromobenzaldehyde diethyl acetal (15.5 g) in tetrahydrofuran (60 mL) The mixture was stirred for 4 hours then the sulfonyl fluoride D4 (5.46 g) was added and the mixture was stirred for 60 ho... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether.Sulfonyl halide | Aldehyde.Sulfone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)CC[NH]CC2 | HF.Br- | O1CCCC1.O | null | 4 | CCOC(OCC)c1ccc(Br)cc1.COc1cc2c(cc1S(=O)(=O)F)CCN(C)CC2>O1CCCC1.O>COc1cc2c(cc1S(=O)(=O)c1ccc(C=O)cc1)CCN(C)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f290ee7300f04238a1f48776ef0e0383 | Brc1ccc(Br)cc1.COc1cc2c(cc1S(=O)(=O)F)CCN(C)CC2>>COc1cc2c(cc1S(=O)(=O)c1ccc(Br)cc1)CCN(C)CC2 | COC=1C(=CC2=C(CCN(CC2)C)C1)S(=O)(=O)F.BrC1=CC=C(C=C1)Br.C(CCC)[Li]>>BrC1=CC=C(C=C1)S(=O)(=O)C1=CC2=C(CCN(CC2)C)C=C1OC | Br[c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1.F[S:9]([c:8]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([cH:7]1)[CH2:19][CH2:20][N:21]([CH3:22])[CH2:23][CH2:24]2)(=[O:10])=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1)[CH2:19][CH2:20][... | Brc1ccc(Br)cc1.COc1cc2c(cc1S(=O)(=O)F)CCN(C)CC2 | COc1cc2c(cc1S(=O)(=O)c1ccc(Br)cc1)CCN(C)CC2 | null | null | O1CCCC1 | Acylation | OtherReaction | 2ad8519fe2b2b4d2e6d223b5c60657948ad1e5cca83b308baf1d818e7b1f5d2e | 5b990d6b86247794ffaed33a136d2856335c1dc26b75f8c5136bcf915ea75fc0 | O=S(=O)(c1ccccc1)c1ccc2c(c1)CCNCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].F-[S;H0;D4;+0:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9](:[c:10]):[c:11]>>[O;D1;H0:7]=[S;H0;D4;+0:6](=[O;D1;H0:8])(-[c:9](:[c:10]):[c:11])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 2 | HOUR | To a stirred solution of 1,4-dibromobenzene (0.665 g, 2.82 mmol, 2.0 eq) in dry tetrahydrofuran (7 mL) under argon at −78° C. was added butyllithium (1.25 mL 2.5M in hexanes, 3.10 mmol, 2.2 eq) dropwise over 10 min. After a further 30 min. a suspension of sulfonyl fluoride D4 (0.385 g, 1.41 mmol, 1.0 eq) was added port... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Sulfonyl halide | Sulfone | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2c(c1)CC[NH]CC2 | Br- | O1CCCC1 | null | 2 | Brc1ccc(Br)cc1.COc1cc2c(cc1S(=O)(=O)F)CCN(C)CC2>O1CCCC1>COc1cc2c(cc1S(=O)(=O)c1ccc(Br)cc1)CCN(C)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-960e7ac0b2c94956a40d2aa634ceda51 | CC(C)(C)OC(=O)N1CCc2ccc(O)cc2CC1.CCI>>CCOc1ccc2c(c1)CCN(C(=O)OC(C)(C)C)CC2 | C(C)I.OC1=CC2=C(CCN(CC2)C(=O)OC(C)(C)C)C=C1.[H-].[Na+]>>C(C)OC1=CC2=C(CCN(CC2)C(=O)OC(C)(C)C)C=C1 | [OH:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]2.I[CH2:2][CH3:1]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]2 | CC(C)(C)OC(=O)N1CCc2ccc(O)cc2CC1.CCI | CCOc1ccc2c(c1)CCN(C(=O)OC(C)(C)C)CC2 | null | null | O.CN(C=O)C.C(C)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2c(c1)CCNCC2 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[OH;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4](:[c:5]):[c:6] | null | [] | null | null | 0.5 | HOUR | To a solution of 7-hydroxy-3-(t-butoxycarbonyl)-2,3,4,5-tetrahydro-1H-3-benzazepine (10 g, 38 mmol) in dimethylformamide (70 mL) was added sodium hydride (60% dispersion in oil, 1.5 g) and the resulting mixture stirred for 0.5 h. Ethyl iodide (3.6 mL, 45 mmol) was added and the mixture stirred for 12 h at 70° C. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CC[NH]CC2 | HI | O.CN(C=O)C.C(C)OCC | null | 0.5 | CC(C)(C)OC(=O)N1CCc2ccc(O)cc2CC1.CCI>O.CN(C=O)C.C(C)OCC>CCOc1ccc2c(c1)CCN(C(=O)OC(C)(C)C)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-50686108a18240839b80a372583cce2c | C=O.COc1cccc(CCN)c1>>COc1ccc2c(c1)CCNC2 | COC=1C=C(CCN)C=CC1.C=O.Cl>>Cl.COC=1C=C2CCNCC2=CC1 | O=[CH2:12].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH2:9][CH2:10][NH2:11])[cH:8]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][NH:11][CH2:12]2 | C=O.COc1cccc(CCN)c1 | COc1ccc2c(c1)CCNC2 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 70d5c5fa4829c190686519bd59ebafece61109628b82676e21fcfe08888b2885 | cf32f1267c674fd84d46b8a676a46bd4e3a018dea282d34ea9ab93d79b66d0ee | c1ccc2c(c1)CCNC2 | O=[CH2;D1;+0:1].[NH2;D1;+0:2]-[C:3]-[C:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[c:9]:[c:8]:[c;H0;D3;+0:7]1:[c:5](:[c:6])-[C:4]-[C:3]-[NH;D2;+0:2]-[CH2;D2;+0:1]-1 | 90 | [{"value": 90.0, "product": "Cl.COC=1C=C2CCNCC2=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a stirred suspension of 3-methoxyphenethylamine (50.4 g, 0.33 mol. 1.0 eq) in water (40 mL) was added 37% aqueous formaldehyde solution (27.5 mL, 1.1 eq) and stirring continued for 20 min. Concentrated HCl (80 mL) was added and the mixture heated at reflux for 1 h. After cooling to room temperature the mixture was e... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Secondary amine | c1ccccc1 | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2 | HO- | O | null | 0.333333 | C=O.COc1cccc(CCN)c1>O>COc1ccc2c(c1)CCNC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-52e84c99d66644eca7520e2124a0a150 | COC(=O)c1ccc(OC)cc1C(=O)OC>>COc1ccc(C(=O)O)c(C(=O)O)c1 | COC=1C=C(C(C(=O)OC)=CC1)C(=O)OC.Cl>>COC=1C=C(C(C(=O)O)=CC1)C(=O)O | C[O:9][C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:14][c:10]1[C:11](=[O:12])[O:13]C)=[O:8]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[c:10]([C:11](=[O:12])[OH:13])[cH:14]1 | COC(=O)c1ccc(OC)cc1C(=O)OC | COc1ccc(C(=O)O)c(C(=O)O)c1 | null | null | [OH-].[Na+] | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8] | null | [] | null | null | null | null | A solution of dimethyl 4-methoxyphthalate (20 g, 89 mmol) was heated at reflux in 10% aqueous sodium hydroxide (85 mL) for 1 hour. The mixture was cooled to room temperature then acidified to pH 1 using concentrated hydrochloric acid. The precipitate that formed was filtered off, washed with water and dried under vacuu... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1 | Other | [OH-].[Na+] | null | null | COC(=O)c1ccc(OC)cc1C(=O)OC>[OH-].[Na+]>COc1ccc(C(=O)O)c(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd0eaf6558a54fb7946bd90212aa4f02 | CN(C)C1(Sc2ccc(Br)cc2)CN(C(=O)OC(C)(C)C)CCc2ccccc21.O=C([O-])c1ccccc1C(=O)O[O-]>>CN(C)C1(S(=O)(=O)c2ccc(Br)cc2)CN(C(=O)OC(C)(C)C)CCc2ccccc21 | S(=O)([O-])[O-].[Na+].[Na+].C(C)(C)(C)OC(=O)N1CCC2=C(C(C1)(N(C)C)SC1=CC=C(C=C1)Br)C=CC=C2.O.O.O.O.O.O.C(C=1C(C(=O)[O-])=CC=CC1)(=O)O[O-].[Mg+2].O.O.O.O.O.O.O.C(C=1C(C(=O)[O-])=CC=CC1)(=O)O[O-].[Mg+2]>>CC(C)(C)OC(=O)N1CCC2=C(C(C1)(N(C)C)S(=O)(=O)C1=CC=C(C=C1)Br)C=CC=C2 | [CH3:1][N:2]([CH3:3])[C:4]1([S:5][c:8]2[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]2)[CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]21.O=C([O-])c1ccccc1C(O[O-:6])=[O:7]>>[CH3:1][N:2]([CH3:3])[C:4]1([S:5](=[O:6])(=[O:7])[c:8]2[cH:9][cH:10][c:... | CN(C)C1(Sc2ccc(Br)cc2)CN(C(=O)OC(C)(C)C)CCc2ccccc21.O=C([O-])c1ccccc1C(=O)O[O-] | CN(C)C1(S(=O)(=O)c2ccc(Br)cc2)CN(C(=O)OC(C)(C)C)CCc2ccccc21 | null | null | ClCCl.CO | Oxidation | OtherReaction | 044ec71636d0bbd77638c539a7db22702f1dcfe130f3df7267fdcef247bbaf2c | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | O=S(=O)(c1ccccc1)C1CNCCc2ccccc21 | O=C(-[O-])-c1:c:c:c:c:c:1-C(=[O;H0;D1;+0:1])-O-[O-;H0;D1:2].[#7:3]-[C:4]-[C:5](-[#7:6])(-[S;H0;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:11]>>[#7:3]-[C:4]-[C:5](-[#7:6])(-[S;H0;D4;+0:7](=[O;H0;D1;+0:2])(=[O;H0;D1;+0:1])-[c:8](:[c:9]):[c:10])-[c:11] | 105.3 | [{"value": 105.3, "product": "CC(C)(C)OC(=O)N1CCC2=C(C(C1)(N(C)C)S(=O)(=O)C1=CC=C(C=C1)Br)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | (4-Bromo-phenylsulfanyl)-dimethylamino-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester (2.8 g, 6.0 mmol) in dichloromethane (5 ml) was added to magnesium monoperoxyphthalate hexahydrate (MMPP) (7.4 g, 80%) in dichloromethane (20 ml) and methanol (3 ml) at 0° C. dropwise. After addition the mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | c1ccccc1 | null | c1ccccc1.c1ccc2c(c1)CC[NH]CC2 | HO- | ClCCl.CO | null | 1 | CN(C)C1(Sc2ccc(Br)cc2)CN(C(=O)OC(C)(C)C)CCc2ccccc21.O=C([O-])c1ccccc1C(=O)O[O-]>ClCCl.CO>CN(C)C1(S(=O)(=O)c2ccc(Br)cc2)CN(C(=O)OC(C)(C)C)CCc2ccccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cab4f33480a74a2e8c8345aa89758166 | CC(C)O.CN1CCc2cc(O)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1>>CC(C)Oc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CCN(C)CC2 | N(=NC(=O)OC(C)C)C(=O)OC(C)C.Br.FC1=CC=C(C=C1)S(=O)(=O)C=1C(=CC2=C(CCN(CC2)C)C1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(C)O>>FC1=CC=C(C=C1)S(=O)(=O)C1=CC2=C(CCN(CC2)C)C=C1OC(C)C | O[CH:2]([CH3:1])[CH3:3].[OH:4][c:5]1[cH:6][c:7]2[c:8]([cH:9][c:10]1[S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]1)[CH2:21][CH2:22][N:23]([CH3:24])[CH2:25][CH2:26]2>>[CH3:1][CH:2]([CH3:3])[O:4][c:5]1[cH:6][c:7]2[c:8]([cH:9][c:10]1[S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][c:17]([F:18])[cH:... | CC(C)O.CN1CCc2cc(O)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1 | CC(C)Oc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CCN(C)CC2 | null | null | O1CCCC1.CO.ClCCl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | aee3d691a6dfc6c8223fef7b9bb4e58ec7e16fbc345d424207a131929cdf1d03 | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | O=S(=O)(c1ccccc1)c1ccc2c(c1)CCNCC2 | O-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C;D1;H3:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 0 | CELSIUS | 1 | HOUR | The phenol (D6) (1.1 g), triphenylphosphine (1.7 g) and isopropanol (0.5 ml) were dissolved in tetrahydrofuran and cooled to 0° C., Diisopropyl azodicarboxylate (1.3 ml) was added dropwise and the mixture stirred at room temperature for 1 h. The mixture was passed through an SCX column and then chromatography on silica... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccc2c(c1)CC[NH]CC2 | HO- | O1CCCC1.CO.ClCCl | 0 | 1 | CC(C)O.CN1CCc2cc(O)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1>O1CCCC1.CO.ClCCl>CC(C)Oc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CCN(C)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f05c9949114a4dd3856211b123cedfc6 | CCI.O=Cc1ccccc1O>>CCOc1cccc(C=O)c1 | C(C)I.O.OC1=C(C=O)C=CC=C1.C([O-])([O-])=O.[K+].[K+]>>C(C)OC=1C=C(C=O)C=CC1 | I[CH2:2][CH3:1].[OH:3][c:4]1[cH:5][cH:6][cH:7][cH:11][c:8]1[CH:9]=[O:10]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH:9]=[O:10])[cH:11]1 | CCI.O=Cc1ccccc1O | CCOc1cccc(C=O)c1 | null | null | CC(=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 26d427df9d715d68fcbb6d1b8554fae49254196de3d80f7e6cc1b02ca1ef3d5b | 4d113d6363da57491050ec895b72d5021ae18d62b0c7a31ae7fa0aba6ea4d07b | c1ccccc1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[O;D1;H0:3]=[C:4]-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[cH;D2;+0:7]:[c:8]:[c:9]:[c;H0;D3;+0:10]:1-[OH;D1;+0:11]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:11]-[c;H0;D3;+0:10]1:[c:9]:[c:8]:[cH;D2;+0:7]:[c;H0;D3;+0:5](-[C:4]=[O;D1;H0:3]):[cH;D2;+0:6]:1 | 90.3 | [{"value": 90.3, "product": "C(C)OC=1C=C(C=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-hydroxybenzaldehyde (20 g, 163 mmol) in acetone (250 mL) was added anhydrous potassium carbonate (33 g, 239 mmol) followed by ethyl iodide (17 mL, 211 mmol). The mixture was heated at reflux for 12 hours. After cooling to room temperature water and ethyl acetate were added. The organic layer was remo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aldehyde.Aromatic alcohol | Aldehyde.Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | CC(=O)C.C(C)(=O)OCC | null | null | CCI.O=Cc1ccccc1O>CC(=O)C.C(C)(=O)OCC>CCOc1cccc(C=O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7468f6f5425a4ab6ada581796ad9d8dc | CCOc1cccc(C=O)c1.C[N+](=O)[O-]>>CCOc1cccc(CC[N+](=O)[O-])c1 | Cl.[N+](=O)([O-])C.C(C)OC=1C=C(C=O)C=CC1.[OH-].[Na+]>>C(C)OC1=CC(=CC=C1)CC[N+](=O)[O-] | O=[CH:9][c:8]1[cH:7][cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:14]1.[CH3:10][N+:11](=[O:12])[O-:13]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][CH2:10][N+:11](=[O:12])[O-:13])[cH:14]1 | CCOc1cccc(C=O)c1.C[N+](=O)[O-] | CCOc1cccc(CC[N+](=O)[O-])c1 | null | null | O.CO | C-C Coupling | OtherReaction | 2aac062ee2f26e6da210ad3b7dbad1aa2850296e05b079b1836469429292aa18 | 9b6235f29075db179203d7e497457b5b3f04cf0f1df0d248730a6d4be5cbe0e1 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[#7;+:6](-[O;-;D1;H0:7])=[O;D1;H0:8]>>[O;-;D1;H0:7]-[#7;+:6](=[O;D1;H0:8])-[CH2;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 37.5 | [{"value": 37.5, "product": "C(C)OC1=CC(=CC=C1)CC[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | null | null | A mixture of nitromethane (0.36 mL, 6.7 mmol) and 3-ethoxy-benzaldehyde (1 g, 6.7 mmol) in methanol (1.4 mL) was cooled to −10° C. To this mixture sodium hydroxide (0.28 g in 1 mL water) was added dropwise. The temperature during addition was maintained around 10° C. After 1 hour a yellow precipitate formed and water (... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Nitro group | null | null | c1ccccc1 | Other | O.CO | -10 | null | CCOc1cccc(C=O)c1.C[N+](=O)[O-]>O.CO>CCOc1cccc(CC[N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36b41ebb896b47749e4443362d11c61f | CCOc1cccc(CC[N+](=O)[O-])c1>>CCOc1cccc(CCN)c1 | [H-].[H-].[H-].[H-].[Li+].[Al+3].C(C)OC1=CC(=CC=C1)CC[N+](=O)[O-]>>C(C)OC=1C=C(C=CC1)CCN | O=[N+:11]([O-])[CH2:10][CH2:9][c:8]1[cH:7][cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:12]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][CH2:10][NH2:11])[cH:12]1 | CCOc1cccc(CC[N+](=O)[O-])c1 | CCOc1cccc(CCN)c1 | null | null | C1CCOC1 | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 53.5 | [{"value": 53.5, "product": "C(C)OC=1C=C(C=CC1)CCN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of LiAlH4 (1M in THF, 13 mL) was added dropwise a solution of 1-ethoxy-3-(2-nitro-ethyl)-benzene (0.5 g, 2.6 mmol) in THF (8 mL). The mixture was refluxed for two hours before allowing to cool and adding dropwise to rochelles salt. The mixture was extracted with ethyl acetate, dried with sodium sulfate an... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | C1CCOC1 | null | null | CCOc1cccc(CC[N+](=O)[O-])c1>C1CCOC1>CCOc1cccc(CCN)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b0f73e038fb84aee8e0beadb0311b188 | C=O.CCOc1cccc(CCN)c1>>CCOc1ccc2c(c1)CCNC2 | C(C)OC=1C=C(C=CC1)CCN.C=O>>C(C)OC=1C=C2CCNCC2=CC1 | O=[CH2:13].[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:10][CH2:11][NH2:12])[cH:9]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]2[c:8]([cH:9]1)[CH2:10][CH2:11][NH:12][CH2:13]2 | C=O.CCOc1cccc(CCN)c1 | CCOc1ccc2c(c1)CCNC2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 70d5c5fa4829c190686519bd59ebafece61109628b82676e21fcfe08888b2885 | cf32f1267c674fd84d46b8a676a46bd4e3a018dea282d34ea9ab93d79b66d0ee | c1ccc2c(c1)CCNC2 | O=[CH2;D1;+0:1].[NH2;D1;+0:2]-[C:3]-[C:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[c:9]:[c:8]:[c;H0;D3;+0:7]1:[c:5](:[c:6])-[C:4]-[C:3]-[NH;D2;+0:2]-[CH2;D2;+0:1]-1 | null | [] | 110 | CELSIUS | null | null | A stirred mixture of 2-(3-ethoxy-phenyl)-ethylamine (7.0 g, 42 mmol) and 37% aqueous formaldehyde solution (3.5 mL) was heated at 110° C. for 30 minutes. The stirring was stopped and the upper water layer was removed by pipette. To the resulting mixture water (5.25 mL) and concentrated HCl (10.5 mL) were added followed... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Secondary amine | c1ccccc1 | c1ccc2c(c1)CCNC2 | c1ccc2c(c1)CCNC2 | HO- | null | 110 | null | C=O.CCOc1cccc(CCN)c1>>CCOc1ccc2c(c1)CCNC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-92285f3590cb4cb1a48b6f87416fb2dd | CCOc1ccc2c(c1)CCN(C(=O)C(F)(F)F)C2.O=S(=O)(O)Cl>>CCOc1cc2c(cc1S(=O)(=O)Cl)CN(C(=O)C(F)(F)F)CC2 | ClS(=O)(=O)O.C(C)OC=1C=C2CCN(CC2=CC1)C(C(F)(F)F)=O>>C(C)OC=1C=C2CCN(CC2=CC1S(=O)(=O)Cl)C(C(F)(F)F)=O | [CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]2[c:7]([cH:8][cH:9]1)[CH2:14][N:15]([C:16](=[O:17])[C:18]([F:19])([F:20])[F:21])[CH2:22][CH2:23]2.O[S:10](=[O:11])(=[O:12])[Cl:13]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]2[c:7]([cH:8][c:9]1[S:10](=[O:11])(=[O:12])[Cl:13])[CH2:14][N:15]([C:16](=[O:17])[C:18]([F:19])([F:20])[F:21])[CH2:2... | CCOc1ccc2c(c1)CCN(C(=O)C(F)(F)F)C2.O=S(=O)(O)Cl | CCOc1cc2c(cc1S(=O)(=O)Cl)CN(C(=O)C(F)(F)F)CC2 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Aromatic sulfonyl chlorination | 08c56726959bc22d6fce4426725906f9f618a4de7e769b972b8c0d4124ab29f2 | d32b60b8f9bfd187c6c9f1eef6a22a00f53525a7532b83aba763d5389c9e4280 | c1ccc2c(c1)CCNC2 | O-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[#8:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4]):[c:9]:[c:10] | null | [] | null | null | 8 | HOUR | To a solution of chlorosulfonic acid (0.48 mL) in dichloromethane (5 mL) at 0° C. was added dropwise a solution of 1-(6-ethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-2,2,2-trifluoro-ethanone (0.39 g, 1.43 mmol). The mixture was stirred at room temperature overnight before partitioning between water and dichloromethane. The o... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CC[NH]C2 | HO- | ClCCl | null | 8 | CCOc1ccc2c(c1)CCN(C(=O)C(F)(F)F)C2.O=S(=O)(O)Cl>ClCCl>CCOc1cc2c(cc1S(=O)(=O)Cl)CN(C(=O)C(F)(F)F)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad90a8a3971b45b2bc09b7a4f4292bd3 | CCOc1cc2c(cc1S(=O)(=O)Cl)CN(C(=O)C(F)(F)F)CC2.[F-]>>CN1CCc2cc(N(C)C)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1 | C([O-])(O)=O.[Na+].C(C)OC=1C=C2CCN(CC2=CC1S(=O)(=O)Cl)C(C(F)(F)F)=O.[F-].[K+]>>FC1=CC=C(C=C1)S(=O)(=O)C=1C(=CC2=C(CCN(CC2)C)C1)N(C)C | O=[C:25]([N:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7](O[CH2:21][CH3:20])[c:11]([S:12](Cl)(=[O:13])=[O:14])[cH:22][c:23]2[CH2:24]1)[C:9](F)(F)F.[F-:19]>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([N:8]([CH3:9])[CH3:10])[c:11]([S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]3)[cH:22][c:23]2[CH2:24][CH... | CCOc1cc2c(cc1S(=O)(=O)Cl)CN(C(=O)C(F)(F)F)CC2.[F-] | CN1CCc2cc(N(C)C)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1 | null | null | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | 219e45de887ff04a222873e5ac3d5ee3e9b9d95d501f7ce62ea78da95032d49c | 90ed1df0f02fb73a8326e5e7ffb30f371e45d46c5534a208f9787b5a5902817a | O=S(=O)(c1ccccc1)c1ccc2c(c1)CCNCC2 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]2:[c:7](:[c:8]:[c;H0;D3;+0:9]:1-O-[CH2;D2;+0:10]-[CH3;D1;+0:11])-[C:12]-[C:13]-[N;H0;D3;+0:14](-[C;H0;D3;+0:15](=O)-[C;H0;D4;+0:16](-F)(-F)-F)-[CH2;D2;+0:17]-2.[F-;H0;D0:18]>>[C;D1;H3:19]-[#7:20](-[CH3;D1;+0:16])-[c;H0;D3;+0:9]1:[c:8]:[c:7]2:[c:6](:[c:5]:[... | 173.9 | [{"value": 173.9, "product": "FC1=CC=C(C=C1)S(=O)(=O)C=1C(=CC2=C(CCN(CC2)C)C1)N(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 6-ethoxy-2-(2,2,2-trifluoro-ethanoyl)-1,2,3,4-tetrahydro-isoquinoline-7-sulfonyl chloride (0.34 g, 0.92 mmol) in acetonitrile (3.8 mL) was added potassium fluoride (0.28 g, 4.8 mmol) and 18-crown-16 (1 crystal). The mixture was stirred at room temperature overnight before addition of aqueous sodium bic... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Ether.Tertiary amide.Sulfonyl halide | Aromatic halide.Tertiary amine.Tertiary amine.Sulfone | c1ccc2c(c1)CC[NH]C2 | c1ccc2c(c1)CC[NH]CC2.c1ccccc1 | c1ccc2c(c1)CC[NH]CC2.c1ccccc1 | null | C(C)#N | null | null | CCOc1cc2c(cc1S(=O)(=O)Cl)CN(C(=O)C(F)(F)F)CC2.[F-]>C(C)#N>CN1CCc2cc(N(C)C)c(S(=O)(=O)c3ccc(F)cc3)cc2CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-df9872deb0d9445d87ae5d0d8f80d9ae | CCOc1cc2c(cc1S(=O)(=O)F)CN(C(=O)C(F)(F)F)CC2.Fc1cc[c]([Mg][Br])cc1>>CCOc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CNCC2 | C(C)OC=1C=C2CCN(CC2=CC1S(=O)(=O)F)C(C(F)(F)F)=O.FC1=CC=C(C=C1)[Mg]Br>>C(C)OC=1C=C2CCNCC2=CC1S(=O)(=O)C1=CC=C(C=C1)F | O=C(C(F)(F)F)[N:21]1[CH2:20][c:7]2[c:6]([cH:5][c:4]([O:3][CH2:2][CH3:1])[c:9]([S:10](F)(=[O:11])=[O:12])[cH:8]2)[CH2:23][CH2:22]1.[Br][Mg][c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]2[c:7]([cH:8][c:9]1[S:10](=[O:11])(=[O:12])[c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1)... | CCOc1cc2c(cc1S(=O)(=O)F)CN(C(=O)C(F)(F)F)CC2.Fc1cc[c]([Mg][Br])cc1 | CCOc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CNCC2 | null | null | C1CCOC1 | Acylation | OtherReaction | 9f330a0f080738f40bea24ae1956d252f5f2f328d36eb2ebd7a13f4cd62a4b43 | 637ba004037973e9decb9a33ed61587de79ee840f11f04991f918ce83c7dbe89 | O=S(=O)(c1ccccc1)c1ccc2c(c1)CNCC2 | F-C(-F)(-F)-C(=O)-[N;H0;D3;+0:1](-[C:2]-[c:3]:[c:4]:[c:5](-[S;H0;D4;+0:6](-F)(=[O;D1;H0:7])=[O;D1;H0:8]):[c:9])-[C:10]-[C:11].[Br]-[Mg]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C:11]-[C:10]-[NH;D2;+0:1]-[C:2]-[c:3]:[c:4]:[c:5](-[S;H0;D4;+0:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:... | null | [] | null | null | 8 | HOUR | To an ice bath cooled solution of 6-ethoxy-2-(2,2,2-trifluoro-ethanoyl)-1,2,3,4-tetrahydro-isoquinoline-7-sulfonyl fluoride (1.30 g, 3.66 mmol) in THF (13 mL) was added dropwise 4-fluorophenylmagnesium bromide (18.3 mL, 18.3 mmol). The mixture was stirred at room temperature overnight before quenching with aqueous sodi... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Trifluoro group.Tertiary amide.Sulfonyl halide | Secondary amine.Sulfone | c1ccc2c(c1)CC[NH]C2.c1ccccc1 | c1ccccc1.c1ccc2c(c1)CCNC2 | c1ccccc1.c1ccc2c(c1)CCNC2 | Br-.Mg | C1CCOC1 | null | 8 | CCOc1cc2c(cc1S(=O)(=O)F)CN(C(=O)C(F)(F)F)CC2.Fc1cc[c]([Mg][Br])cc1>C1CCOC1>CCOc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CNCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e3d57e90e24f442b8a01474c6fd65590 | Nc1ccc(Br)cc1.O=CO>>O=CNc1ccc(Br)cc1 | C(=O)O.C(C)(=O)OC(C)=O.BrC1=CC=C(N)C=C1>>BrC1=CC=C(C=C1)NC=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1.O[CH:2]=[O:1]>>[O:1]=[CH:2][NH:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1 | Nc1ccc(Br)cc1.O=CO | O=CNc1ccc(Br)cc1 | null | null | C1CCOC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[CH;D2;+0:1]=[O;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6] | 70.9 | [{"value": 70.9, "product": "BrC1=CC=C(C=C1)NC=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Formic acid (7 mL, 186 mmol) and acetic anhydride (140.1 mL, 150 mmol) were heated together at 55° C. for 2 hours. The mixture was cooled to room temperature, THF (11 mL) was added followed by 4-bromoaniline (10 g, 58 mmol) in THF (20 mL). The mixture was stirred at room temperature for 3 hours before evaporating to dr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | C1CCOC1 | null | 3 | Nc1ccc(Br)cc1.O=CO>C1CCOC1>O=CNc1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-684f4c64fb3a49e28cba37aa5a313993 | O=CNc1ccc(Br)cc1>>CNc1ccc(Br)cc1 | [OH-].[Na+].Cl.BrC1=CC=C(C=C1)NC=O.B(F)(F)F.CCOCC>>BrC1=CC=C(C=C1)NC | O=[CH:1][NH:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1>>[CH3:1][NH:2][c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1 | O=CNc1ccc(Br)cc1 | CNc1ccc(Br)cc1 | null | null | C1CCOC1 | Reduction | OtherReaction | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccccc1 | O=[CH;D2;+0:1]-[#7:2]-[c:3]>>[CH3;D1;+0:1]-[#7:2]-[c:3] | null | [] | null | null | 1 | HOUR | To a solution of N-(4-Bromo-phenyl)-formamide D32a (8.2 g, 41 mmol) in dry THF (100 mL) was added BF3.Et2O (8.2 mL, 61 mmol). The mixture was heated to reflux and BH3. THF (103 mL, 103 mmol) added dropwise, the mixture was heated for a further 2 hours. After cooling to room temperature concentrated HCl (100 mL) was add... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1 | Other | C1CCOC1 | null | 1 | O=CNc1ccc(Br)cc1>C1CCOC1>CNc1ccc(Br)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c54df880540c4dddbfd6c5b7e9c8d141 | O=C(N1CCc2ccc(S(=O)(=O)F)cc2CC1)C(F)(F)F.O=C1CCC(=O)N1I>>O=C(N1CCc2cc(S(=O)(=O)F)cc(I)c2CC1)C(F)(F)F | S(=O)([O-])[O-].[Na+].[Na+].C(O)([O-])=O.[Na+].FC(C(=O)N1CCC2=C(CC1)C=CC(=C2)S(=O)(=O)F)(F)F.IN1C(CCC1=O)=O>>FC(C(=O)N1CCC2=C(CC1)C(=CC(=C2)S(=O)(=O)F)I)(F)F | [O:1]=[C:2]([N:3]1[CH2:4][CH2:5][c:6]2[cH:7][cH:13][c:8]([S:9](=[O:10])(=[O:11])[F:12])[cH:14][c:16]2[CH2:17][CH2:18]1)[C:19]([F:20])([F:21])[F:22].O=C1CCC(=O)N1[I:15]>>[O:1]=[C:2]([N:3]1[CH2:4][CH2:5][c:6]2[cH:7][c:8]([S:9](=[O:10])(=[O:11])[F:12])[cH:13][c:14]([I:15])[c:16]2[CH2:17][CH2:18]1)[C:19]([F:20])([F:21])[F:... | O=C(N1CCc2ccc(S(=O)(=O)F)cc2CC1)C(F)(F)F.O=C1CCC(=O)N1I | O=C(N1CCc2cc(S(=O)(=O)F)cc(I)c2CC1)C(F)(F)F | null | null | FC(S(=O)(=O)O)(F)F | Functional Group Interconversion | OtherReaction | f7b05dea4b03981806ef03662eb6ab107185a1934650d49c256f196f61d6bff0 | 4ecbd0e25a7e72624ae9b9490ec32bd053132f892e8f9c2d48aba99121240c9d | c1ccc2c(c1)CCNCC2 | O=C1-C-C-C(=O)-N-1-[I;H0;D1;+0:1].[C:2]-[c:3]1:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[#16:6](-[F;D1;H0:7])(=[O;D1;H0:8])=[O;D1;H0:9]):[cH;D2;+0:10]:[cH;D2;+0:11]:[c:12]:1-[C:13]>>[C:2]-[c:3]1:[c:12](:[cH;D2;+0:11]:[c;H0;D3;+0:5](-[#16:6](-[F;D1;H0:7])(=[O;D1;H0:8])=[O;D1;H0:9]):[cH;D2;+0:10]:[c;H0;D3;+0:4]:1-[I;H0;D1;+0:1])-[C:... | 67.8 | [{"value": 67.8, "product": "FC(C(=O)N1CCC2=C(CC1)C(=CC(=C2)S(=O)(=O)F)I)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3-trifluoroacetyl-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonyl fluoride (D1) (5.3 g, 17 mmol) in trifluoromethanesulfonic acid (30 ml) at 0° C. was added portionwise N-iodosuccinimide (5.9 g, 25 mmol). The resulting solution was stirred for 1 h without cooling then poured into saturated aqueous sodium h... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Sulfonyl halide | Aromatic halide.Sulfonyl halide | c1ccc2c(c1)CC[NH]CC2.C1CCNC1 | c1ccc2c(c1)CC[NH]CC2 | c1ccc2c(c1)CC[NH]CC2 | HO- | FC(S(=O)(=O)O)(F)F | null | 1 | O=C(N1CCc2ccc(S(=O)(=O)F)cc2CC1)C(F)(F)F.O=C1CCC(=O)N1I>FC(S(=O)(=O)O)(F)F>O=C(N1CCc2cc(S(=O)(=O)F)cc(I)c2CC1)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-53c8c78f7b5a4025936fe3f2f7dc9b60 | Fc1cc[c]([Mg][Cl])cc1.O=C(N1CCc2cc(S(=O)(=O)F)cc(I)c2CC1)C(F)(F)F>>O=S(=O)(c1ccc(F)cc1)c1cc(I)c2c(c1)CCNCC2 | C(=O)([O-])C(O)C(O)C(=O)[O-].[K+].[Na+].FC(C(=O)N1CCC2=C(CC1)C(=CC(=C2)S(=O)(=O)F)I)(F)F.FC1=CC=C(C=C1)[Mg]Cl>>FC1=CC=C(C=C1)S(=O)(=O)C1=CC2=C(CCNCC2)C(=C1)I | [Cl][Mg][c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1.O=C(C(F)(F)F)[N:20]1[CH2:19][CH2:18][c:16]2[c:15]([c:13]([I:14])[cH:12][c:11]([S:2](F)(=[O:1])=[O:3])[cH:17]2)[CH2:22][CH2:21]1>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][cH:10]1)[c:11]1[cH:12][c:13]([I:14])[c:15]2[c:16]([cH:17]1)[CH2:18][CH2:19][NH:20... | Fc1cc[c]([Mg][Cl])cc1.O=C(N1CCc2cc(S(=O)(=O)F)cc(I)c2CC1)C(F)(F)F | O=S(=O)(c1ccc(F)cc1)c1cc(I)c2c(c1)CCNCC2 | null | null | O1CCCC1 | Acylation | OtherReaction | a8041dd1d68e41fd28bc65f8e638921fdb41157593f497948b1eeb7de2cd26b6 | 637ba004037973e9decb9a33ed61587de79ee840f11f04991f918ce83c7dbe89 | O=S(=O)(c1ccccc1)c1ccc2c(c1)CCNCC2 | F-C(-F)(-F)-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].F-[S;H0;D4;+0:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9](:[c:10]):[c:11].[Cl]-[Mg]-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5].[O;D1;H0:7]=[S;H0;D4;+0:6](=[O;D1;H0:8])(-[c:9](:[c:10]):[c:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:... | 48.4 | [{"value": 48.4, "product": "FC1=CC=C(C=C1)S(=O)(=O)C1=CC2=C(CCNCC2)C(=C1)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of 3-trifluoroacetyl-9-iodo-1,2,4,5-tetrahydro-3-benzazepine-7-sulfonyl fluoride (5.29, 11.5 mmol) in tetrahydrofuran (50 ml) was added 4-fluorophenylmagnesium chloride (50 ml, 1M in tetrahydrofuran, 50 mmol). The resulting solution was stirred for 18 h without cooling then poured into saturated aqueous s... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Trifluoro group.Tertiary amide.Sulfonyl halide | Secondary amine.Sulfone | c1ccccc1.c1ccc2c(c1)CC[NH]CC2 | c1ccccc1.c1ccc2c(c1)CCNCC2 | c1ccccc1.c1ccc2c(c1)CCNCC2 | Mg | O1CCCC1 | null | 18 | Fc1cc[c]([Mg][Cl])cc1.O=C(N1CCc2cc(S(=O)(=O)F)cc(I)c2CC1)C(F)(F)F>O1CCCC1>O=S(=O)(c1ccc(F)cc1)c1cc(I)c2c(c1)CCNCC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-45fb89563ed648a7b54d0cd553d9bb33 | C=O.O=S(=O)(c1ccc(F)cc1)c1cc(I)c2c(c1)CCNCC2>>CN1CCc2cc(S(=O)(=O)c3ccc(F)cc3)cc(I)c2CC1 | O.FC1=CC=C(C=C1)S(=O)(=O)C1=CC2=C(CCNCC2)C(=C1)I.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].C=O>>CN1CCC2=C(CC1)C(=CC(=C2)S(=O)(=O)C2=CC=C(C=C2)F)I | O=[CH2:1].[NH:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([S:8](=[O:9])(=[O:10])[c:11]3[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]3)[cH:18][c:19]([I:20])[c:21]2[CH2:22][CH2:23]1>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([S:8](=[O:9])(=[O:10])[c:11]3[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]3)[cH:18][c:19]([I:20])[c:21]2[CH2:... | C=O.O=S(=O)(c1ccc(F)cc1)c1cc(I)c2c(c1)CCNCC2 | CN1CCc2cc(S(=O)(=O)c3ccc(F)cc3)cc(I)c2CC1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | 8d9cad772a98a414ce55384bd0cd4b440b5a4763409ac2b73eace6e178c9f3d7 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | O=S(=O)(c1ccccc1)c1ccc2c(c1)CCNCC2 | O=[CH2;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[C:5]-[C:6] | 98 | [{"value": 98.0, "product": "CN1CCC2=C(CC1)C(=CC(=C2)S(=O)(=O)C2=CC=C(C=C2)F)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 7-(4-fluorophenylsulfonyl)-9-iodo-1,2,4,5-tetrahydro-3-benzazepine (2.4 g, 5.5 mmol) in dichloromethane (20 ml) were added sodium triacetoxyborohydride (1.8 g, 8.5 mmol) and formalin (1 ml, 37%, 12 mmol). The mixture was stirred for 2 h without cooling then poured into water (100 ml) and extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | c1ccc2c(c1)CCNCC2 | c1ccc2c(c1)CC[NH]CC2 | c1ccc2c(c1)CC[NH]CC2.c1ccccc1 | Other | ClCCl | null | 2 | C=O.O=S(=O)(c1ccc(F)cc1)c1cc(I)c2c(c1)CCNCC2>ClCCl>CN1CCc2cc(S(=O)(=O)c3ccc(F)cc3)cc(I)c2CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-77b6ebea9ae740e98152eae62cd359e5 | CN1CCc2cc(S(=O)(=O)c3ccc(F)cc3)cc(I)c2CC1.OB(O)c1ccccc1>>CN1CCc2cc(S(=O)(=O)c3ccc(F)cc3)cc(-c3ccccc3)c2CC1 | CN1CCC2=C(CC1)C(=CC(=C2)S(=O)(=O)C2=CC=C(C=C2)F)I.C1(=CC=CC=C1)B(O)O.C([O-])([O-])=O.[K+].[K+].C(C)O>>CN1CCC2=C(CC1)C(=CC(=C2)S(=O)(=O)C2=CC=C(C=C2)F)C2=CC=CC=C2 | I[c:19]1[cH:18][c:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]2)[cH:6][c:5]2[c:26]1[CH2:27][CH2:28][N:2]([CH3:1])[CH2:3][CH2:4]2.OB(O)[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][N:2]1[CH2:3][CH2:4][c:5]2[cH:6][c:7]([S:8](=[O:9])(=[O:10])[c:11]3[cH:12][cH:13][c:14]([F:15])[cH:16][c... | CN1CCc2cc(S(=O)(=O)c3ccc(F)cc3)cc(I)c2CC1.OB(O)c1ccccc1 | CN1CCc2cc(S(=O)(=O)c3ccc(F)cc3)cc(-c3ccccc3)c2CC1 | null | null | O.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | 7f1ca6395038443942566abe4f2d8e9ec4c2f872967e5e1105bc507e942be742 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1ccccc1)c1cc2c(c(-c3ccccc3)c1)CCNCC2 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5])-[C:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[C:6]-[c:4](:[c:5]):[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[c:2]:[c:3] | 75.9 | [{"value": 75.9, "product": "CN1CCC2=C(CC1)C(=CC(=C2)S(=O)(=O)C2=CC=C(C=C2)F)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of 3-methyl-7-(4fluorophenylsulfonyl)-9-iodo-1,2,4,5-tetrahydro-3-benzazepine (0.9 g, 2 mmol), phenylboronic acid (0.4 g, 3 mmol), potassium carbonate (1.6 g, 12 mmol), ethanol (6 ml), water (6 ml), and toluene (25 ml) was degassed, then tetrakis(triphenylphosphine)palladium (0) (100 mg) was added and the mix... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)CC[NH]CC2.c1ccccc1 | c1ccc2c(c1)CC[NH]CC2.c1ccccc1 | c1ccc2c(c1)CC[NH]CC2.c1ccccc1.c1ccccc1 | HI.B | O.C1(=CC=CC=C1)C | 60 | null | CN1CCc2cc(S(=O)(=O)c3ccc(F)cc3)cc(I)c2CC1.OB(O)c1ccccc1>O.C1(=CC=CC=C1)C>CN1CCc2cc(S(=O)(=O)c3ccc(F)cc3)cc(-c3ccccc3)c2CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bd6c72de39f6491b9953327da01f3109 | C=O.COc1cc2c(cc1S(=O)(=O)c1cccc(Oc3ccccc3)c1)CCNCC2>>COc1cc2c(cc1S(=O)(=O)c1cccc(Oc3ccccc3)c1)CCN(C)CC2 | Cl.COC1=CC2=C(CCNCC2)C=C1S(=O)(=O)C1=CC(=CC=C1)OC1=CC=CC=C1.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].C=O.ClCCCl>>Cl.COC1=CC2=C(CCN(CC2)C)C=C1S(=O)(=O)C1=CC(=CC=C1)OC1=CC=CC=C1 | O=[CH2:28].[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][c:16]([O:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[cH:24]1)[CH2:25][CH2:26][NH:27][CH2:29][CH2:30]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][c:... | C=O.COc1cc2c(cc1S(=O)(=O)c1cccc(Oc3ccccc3)c1)CCNCC2 | COc1cc2c(cc1S(=O)(=O)c1cccc(Oc3ccccc3)c1)CCN(C)CC2 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | 8d9cad772a98a414ce55384bd0cd4b440b5a4763409ac2b73eace6e178c9f3d7 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | O=S(=O)(c1cccc(Oc2ccccc2)c1)c1ccc2c(c1)CCNCC2 | O=[CH2;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[C:5]-[C:6] | null | [] | null | null | 18 | HOUR | A mixture of E1 hydrochloride salt (0.2 g, 0.5 mmol), sodium triacetoxyborohydride (400 MG), aqueous formaldehyde (0.5 mL, 37%), and 1,2-dichloroethane (10 mL containing 0.5 mL triethylamine) was stirred for 18 h then diluted with dichloromethane (50 mL) and washed with saturated aqueous sodium hydrogen carbonate (100 ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | c1ccc2c(c1)CCNCC2 | c1ccc2c(c1)CC[NH]CC2 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CC[NH]CC2 | Other | ClCCl | null | 18 | C=O.COc1cc2c(cc1S(=O)(=O)c1cccc(Oc3ccccc3)c1)CCNCC2>ClCCl>COc1cc2c(cc1S(=O)(=O)c1cccc(Oc3ccccc3)c1)CCN(C)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8b51d42ca3ac406ea1cccb22ac516ba1 | BrCc1ccccc1.CC(C)(C)OC(=O)N1CCc2ccc(S(=O)(=O)c3cccc(O)c3)cc2CC1>>CC(C)(C)OC(=O)N1CCc2ccc(S(=O)(=O)c3cccc(OCc4ccccc4)c3)cc2CC1 | C(C1=CC=CC=C1)Br.OC=1C=C(C=CC1)S(=O)(=O)C1=CC2=C(CCN(CC2)C(=O)OC(C)(C)C)C=C1.[H-].[Na+]>>C(C1=CC=CC=C1)OC=1C=C(C=CC1)S(=O)(=O)C1=CC2=C(CCN(CC2)C(=O)OC(C)(C)C)C=C1 | Br[CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([S:15](=[O:16])(=[O:17])[c:18]3[cH:19][cH:20][cH:21][c:22]([OH:23])[cH:31]3)[cH:32][c:33]2[CH2:34][CH2:35]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9... | BrCc1ccccc1.CC(C)(C)OC(=O)N1CCc2ccc(S(=O)(=O)c3cccc(O)c3)cc2CC1 | CC(C)(C)OC(=O)N1CCc2ccc(S(=O)(=O)c3cccc(OCc4ccccc4)c3)cc2CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | O=S(=O)(c1cccc(OCc2ccccc2)c1)c1ccc2c(c1)CCNCC2 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 60.5 | [{"value": 60.5, "product": "C(C1=CC=CC=C1)OC=1C=C(C=CC1)S(=O)(=O)C1=CC2=C(CCN(CC2)C(=O)OC(C)(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of D3 (270 mg, 0.67 mmol) in dimethylformamide (5 mL) was treated with 60% sodium hydride (40 mg) at 0° C., then allowed to warm to room temperature. Benzyl bromide (137 mg, 0.8 mmol) in dimethylformamide (2 mL) was added, and the solution stirred overnight. The mixture was then poured onto water and extract... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2c(c1)CC[NH]CC2.c1ccccc1.c1ccccc1 | HBr | CN(C=O)C | null | 8 | BrCc1ccccc1.CC(C)(C)OC(=O)N1CCc2ccc(S(=O)(=O)c3cccc(O)c3)cc2CC1>CN(C=O)C>CC(C)(C)OC(=O)N1CCc2ccc(S(=O)(=O)c3cccc(OCc4ccccc4)c3)cc2CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d4710f0d5c0440caa1a445c8db455730 | COc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CCN(C)CC2.OCc1ccc(Cl)cc1>>COc1cc2c(cc1S(=O)(=O)c1ccc(OCc3ccc(Cl)cc3)cc1)CCN(C)CC2 | Cl.[H-].[Na+].ClC1=CC=C(CO)C=C1.FC1=CC=C(C=C1)S(=O)(=O)C1=CC2=C(CCN(CC2)C)C=C1OC>>Cl.ClC1=CC=C(COC2=CC=C(C=C2)S(=O)(=O)C2=CC3=C(CCN(CC3)C)C=C2OC)C=C1 | F[c:15]1[cH:14][cH:13][c:12]([S:9]([c:8]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([cH:7]2)[CH2:27][CH2:28][N:29]([CH3:30])[CH2:31][CH2:32]3)(=[O:10])=[O:11])[cH:26][cH:25]1.[OH:16][CH2:17][c:18]1[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[S:9](=[O:10])(=[O:11])[c:12]1[cH:1... | COc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CCN(C)CC2.OCc1ccc(Cl)cc1 | COc1cc2c(cc1S(=O)(=O)c1ccc(OCc3ccc(Cl)cc3)cc1)CCN(C)CC2 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | O=S(=O)(c1ccc(OCc2ccccc2)cc1)c1ccc2c(c1)CCNCC2 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[OH;D1;+0:6]-[C:7]-[c:8]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:6]-[C:7]-[c:8]):[c:4]:[c:5] | null | [] | 40 | CELSIUS | 15 | MINUTE | Sodium hydride (60% in oil) (2.52 g, 63 mmol) was suspended in dry dimethylsulfoxide (30 mL) and 4-chlorobenzyl alcohol (12 g, 84 mmol) in dry dimethylsulfoxide (30 mL) was added over 15 min by syringe keeping the temperature below 30° C. (internal). This solution was stirred for 15 minutes to give a grey clear solutio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccc2c(c1)CC[NH]CC2 | HF | CS(=O)C | 40 | 0.25 | COc1cc2c(cc1S(=O)(=O)c1ccc(F)cc1)CCN(C)CC2.OCc1ccc(Cl)cc1>CS(=O)C>COc1cc2c(cc1S(=O)(=O)c1ccc(OCc3ccc(Cl)cc3)cc1)CCN(C)CC2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6705e99bb3be4740825ec1a8e362f849 | COc1cc2c(cc1S(=O)(=O)c1ccc(CO)cc1)CCN(C)CC2.Oc1ccc(Cl)cc1>>COc1cc2c(cc1S(=O)(=O)c1ccc(COc3ccc(Cl)cc3)cc1)CCN(C)CC2.Cl | COC=1C(=CC2=C(CCN(CC2)C)C1)S(=O)(=O)C1=CC=C(C=C1)CO.ClC1=CC=C(C=C1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=NC(=O)OC(C)C)C(=O)OC(C)C>>Cl.ClC1=CC=C(OCC2=CC=C(C=C2)S(=O)(=O)C2=CC3=C(CCN(CC3)C)C=C2OC)C=C1 | O[CH2:16][c:15]1[cH:14][cH:13][c:12]([S:9]([c:8]2[c:3]([O:2][CH3:1])[cH:4][c:5]3[c:6]([cH:7]2)[CH2:27][CH2:28][N:29]([CH3:30])[CH2:31][CH2:32]3)(=[O:10])=[O:11])[cH:26][cH:25]1.[OH:17][c:18]1[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[S:9](=[O:10])(=[O:11])[c:12]1[cH:1... | COc1cc2c(cc1S(=O)(=O)c1ccc(CO)cc1)CCN(C)CC2.Oc1ccc(Cl)cc1 | COc1cc2c(cc1S(=O)(=O)c1ccc(COc3ccc(Cl)cc3)cc1)CCN(C)CC2.Cl | null | null | O1CCCC1 | Functional Group Interconversion | Mitsunobu aryl ether | a813c8c5299b9ca52205848e98417aa39611779e13b2094d6922e6ded90b0789 | f8982f47f8461b9eb1ca09f034c55cfcbd62a43df12f9fa99bf4f6938573fbf7 | O=S(=O)(c1ccc(COc2ccccc2)cc1)c1ccc2c(c1)CCNCC2 | 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] | null | [] | null | null | 18 | HOUR | A solution of [4-(8-methoxy-3-methyl-2,3,4,5-tetrahydro-1-H-3-benzazepine-7-sulfonyl)-phenyl]-methanol D12 (0.12 g), 4-chlorophenol (0.042 g), triphenyl phosphine (0.087 g in tetrahydrofuran (5 mL) was treated with diisopropyl azodicarboxylate (0.066 g). The solution was stirred for 18 hour then the solvent was evapora... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)CC[NH]CC2 | null | O1CCCC1 | null | 18 | COc1cc2c(cc1S(=O)(=O)c1ccc(CO)cc1)CCN(C)CC2.Oc1ccc(Cl)cc1>O1CCCC1>COc1cc2c(cc1S(=O)(=O)c1ccc(COc3ccc(Cl)cc3)cc1)CCN(C)CC2.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6a08549888914b82a2f82521f1f35637 | CN(C)C=O.CN1CCc2cc(N(C)C)c(S(=O)(=O)c3ccc(Br)cc3)cc2CC1>>CN(C)C1(C)CNCCc2cc(S(=O)(=O)c3ccc(C=O)cc3)ccc21 | [Cl-].[NH4+].C(CCC)[Li].BrC1=CC=C(C=C1)S(=O)(=O)C=1C(=CC2=C(CCN(CC2)C)C1)N(C)C.O1CCCC1.CN(C=O)C>>CN(C)C1(CNCCC2=C1C=CC(=C2)S(=O)(=O)C2=CC=C(C=O)C=C2)C | CN(C)[CH:20]=[O:21].Br[c:19]1[cH:18][cH:17][c:16]([S:13]([c:12]2[cH:11][c:10]3[c:26]([cH:25][c:24]2[N:2]([CH3:1])[CH3:3])[CH2:4][CH2:6][N:7]([CH3:5])[CH2:8][CH2:9]3)(=[O:14])=[O:15])[cH:23][cH:22]1>>[CH3:1][N:2]([CH3:3])[C:4]1([CH3:5])[CH2:6][NH:7][CH2:8][CH2:9][c:10]2[cH:11][c:12]([S:13](=[O:14])(=[O:15])[c:16]3[cH:17... | CN(C)C=O.CN1CCc2cc(N(C)C)c(S(=O)(=O)c3ccc(Br)cc3)cc2CC1 | CN(C)C1(C)CNCCc2cc(S(=O)(=O)c3ccc(C=O)cc3)ccc21 | null | null | null | C-C Coupling | OtherReaction | 7206a498cd06f22153cf33764dfd81b017db539a3eed8b5fb14bffb21cf68af5 | 1e3d7a021393e2f12b9ffb3dc2e10bfb80f619b5ef977a323e8a43c83e2572e6 | O=S(=O)(c1ccccc1)c1ccc2c(c1)CCNCC2 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#16:6]-[c:7]1:[c:8]:[c:9]2:[c:10](:[c:11]:[c;H0;D3;+0:12]:1-[N;H0;D3;+0:13](-[C;D1;H3:14])-[C;D1;H3:15])-[CH2;D2;+0:16]-[C:17]-[N;H0;D3;+0:18](-[CH3;D1;+0:19])-[C:20]-[C:21]-2.C-N(-C)-[CH;D2;+0:22]=[O;D1;H0:23]>>[#16:6]-[c:7]1:[c:8]:[c:9]2:[c:10](:[c:11]:[cH;D2;+0:12]:1)-[C;... | null | [] | null | null | 2 | MINUTE | [8-(4-Bromo-benzenesulfonyl)3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]-dimethyl-amine (D28) (1.4 g, 3.4 mmol) was cooled to −78° C. in tetrahydrofuran (20 ml) under an argon atmosphere. n-Butyllithium (1.6 ml, 2.5M) was added dropwise and the mixture stirred for 2 mins. Dimethylformamide (300 mg) was added and t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide.Tertiary amine.Tertiary amine | Aldehyde.Secondary amine.Tertiary amine | c1ccccc1.c1ccc2c(c1)CC[NH]CC2 | c1ccc2c(c1)CCNCC2.c1ccccc1 | c1ccc2c(c1)CCNCC2.c1ccccc1 | HBr | null | null | 0.033333 | CN(C)C=O.CN1CCc2cc(N(C)C)c(S(=O)(=O)c3ccc(Br)cc3)cc2CC1>>CN(C)C1(C)CNCCc2cc(S(=O)(=O)c3ccc(C=O)cc3)ccc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a8f988beeb86475a8f9191addea1957b | CC(=O)c1cccc(O)c1.CN(C)C(=O)Cl>>CC(=O)c1cccc(OC(=O)N(C)C)c1 | [Cl-].[Na+].OC=1C=C(C=CC1)C(C)=O.[H-].[Na+].CN(C(=O)Cl)C>>CN(C(OC1=CC(=CC=C1)C(C)=O)=O)C | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:15]1.Cl[C:10](=[O:11])[N:12]([CH3:13])[CH3:14]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][C:10](=[O:11])[N:12]([CH3:13])[CH3:14])[cH:15]1 | CC(=O)c1cccc(O)c1.CN(C)C(=O)Cl | CC(=O)c1cccc(OC(=O)N(C)C)c1 | null | null | O1CCCC1 | Protection | Schotten-Baumann to ester | 76fc23af07d8d02fec539138b5d326dfd4e833212bae1d173120f54983c8b7d8 | 4c7d92b589147a4e2aa8407ff52bd0eb1be84bdb6595779d27beb0c5d6fdd0e2 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C;D1;H3:4])-[C;D1;H3:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H3:4]-[#7:3](-[C;D1;H3:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | 166.1 | [{"value": 166.1, "product": "CN(C(OC1=CC(=CC=C1)C(C)=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Tetrahydrofuran (100 ml) was added to sodium hydride (1.94 g, 45 mmol) under an atmosphere of nitrogen. To the suspension was added a tetrahydrofuran solution of 1-(3-hydroxyphenyl)ethanone (5.05 g, 37 mmol) in an ice bath. After stirring the mixture for 15 minutes dimethylcarbamyl chloride (1.7 ml, 19 mmol) was added ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Aromatic alcohol | Carbamic ester | null | null | c1ccccc1 | HCl | O1CCCC1 | null | 4 | CC(=O)c1cccc(O)c1.CN(C)C(=O)Cl>O1CCCC1>CC(=O)c1cccc(OC(=O)N(C)C)c1 |
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