dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5829e421f6d240ab92acd0e56ae1352b | CC1CNCCN1.Cc1ccccc1S(=O)(=O)n1ccc2c(Br)cccc21>>Cc1ccccc1S(=O)(=O)n1ccc2c(N3CCNC(C)C3)cccc21 | BrC1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=C(C=CC=C1)C.CC1CNCCN1>>CC1CN(CCN1)C1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=C(C=CC=C1)C | [NH:16]1[CH2:17][CH2:18][NH:19][CH:20]([CH3:21])[CH2:22]1.Br[c:15]1[c:14]2[cH:13][cH:12][n:11]([S:8]([c:7]3[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]3)(=[O:9])=[O:10])[c:26]2[cH:25][cH:24][cH:23]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[n:11]1[cH:12][cH:13][c:14]2[c:15]([N:16]3[CH2:17][CH2:18][NH... | CC1CNCCN1.Cc1ccccc1S(=O)(=O)n1ccc2c(Br)cccc21 | Cc1ccccc1S(=O)(=O)n1ccc2c(N3CCNC(C)C3)cccc21 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 00599bbbffced01cd2985ebc9fbf67df1bcefb20b1163f91a23a7b690b4821bf | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=S(=O)(c1ccccc1)n1ccc2c(N3CCNCC3)cccc21 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[#16:7]):[c:8]:[c:9]:[c:10]:2:1.[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[#16:7]-[#7;a:6]1:[c:8]:[c:9]:[c:10]2:[c:5]:1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:2-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:16]-[C:15]-1 | 38 | [{"value": 38.0, "product": "CC1CN(CCN1)C1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=C(C=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The compound was prepared from 4-bromo-1-(2-methyl-benzenesulfonyl)-1H-indole and 3-methylpiperazine according to Method 1 to give 110 mg (38%) of a white solid: 1HNMR (CD3OD) δ 7.92–6.82 (m, 9H), 3.64–3.39 (m, 5H), 3.12–3.03 (m, 1H), 2.92–2.83 (m, 1H), 2.47 (s, 3H), 1.40 (d, J=7 Hz, 3H); MS (ESI) 370.0 (M+H)+; Purity ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cccc2[nH]ccc12 | C1C[NH]CCN1.c1cccc2[nH]ccc12 | c1ccccc1.C1C[NH]CCN1.c1cccc2[nH]ccc12 | HBr | null | null | null | CC1CNCCN1.Cc1ccccc1S(=O)(=O)n1ccc2c(Br)cccc21>>Cc1ccccc1S(=O)(=O)n1ccc2c(N3CCNC(C)C3)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-70012c0a48024771b36f75aabd29de67 | CN1C[C@@H]2C[C@H]1CN2.Cc1ccccc1S(=O)(=O)n1ccc2c(Br)cccc21>>Cc1ccccc1S(=O)(=O)n1ccc2c([C@@]34CN[C@H](CN3C)C4)cccc21 | BrC1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=C(C=CC=C1)C.CN1[C@@H]2CN[C@H](C1)C2>>CN1[C@]2(CN[C@H](C1)C2)C2=C1C=CN(C1=CC=C2)S(=O)(=O)C2=C(C=CC=C2)C | [C@H:16]12[CH2:17][NH:18][C@H:19]([CH2:20][N:21]1[CH3:22])[CH2:23]2.Br[c:15]1[c:14]2[cH:13][cH:12][n:11]([S:8]([c:7]3[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]3)(=[O:9])=[O:10])[c:27]2[cH:26][cH:25][cH:24]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[S:8](=[O:9])(=[O:10])[n:11]1[cH:12][cH:13][c:14]2[c:15]([C@@:16]34[CH2:1... | CN1C[C@@H]2C[C@H]1CN2.Cc1ccccc1S(=O)(=O)n1ccc2c(Br)cccc21 | Cc1ccccc1S(=O)(=O)n1ccc2c([C@@]34CN[C@H](CN3C)C4)cccc21 | null | null | null | C-C Coupling | OtherReaction | 21e20e13bace8be3fc08b2a1b2625699533da7e5587fa2d95baf7c5f850536e0 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | O=S(=O)(c1ccccc1)n1ccc2c([C@@]34CN[C@H](CN3)C4)cccc21 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[#16:7]):[c:8]:[c:9]:[c:10]:2:1.[C;D1;H3:11]-[#7:12]1-[C:13]-[C:14]2-[#7:15]-[C:16]-[C@@H;D3;+0:17]-1-[C:18]-2>>[#16:7]-[#7;a:6]1:[c:8]:[c:9]:[c:10]2:[c:5]:1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:2-[C@@;H0;D4;+0:17]12-[C:16]-[#7:15]-[C:14](-[C:13]-[#7:12]-1-[C;D1;H3:11])... | 19 | [{"value": 19.0, "product": "CN1[C@]2(CN[C@H](C1)C2)C2=C1C=CN(C1=CC=C2)S(=O)(=O)C2=C(C=CC=C2)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The compound was prepared from 4-bromo-1-(2-methyl-benzenesulfonyl)-1H-indole and (1S,4S)-2-methyl-2,5-diazabicyclo[2.2.1]heptane according to Method 1 to give 25 mg (19%) of a white solid: 1H NMR (CD3OD) δ 7.91–6.44 (m, 9H), 4.67–4.63 (m, 1H), 4.35–4.33 (m, 1H), 4.09–4.07 (m, 1H), 3.99–3.95 (m, 1H), 3.72–3.70 (m, 1H),... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | C1N[C@@H]2C[NH][C@H]1C2.c1cccc2[nH]ccc12 | C1N[C@@H]2C[NH][C@H]1C2.c1cccc2[nH]ccc12 | C1N[C@@H]2C[NH][C@H]1C2.c1ccccc1.c1cccc2[nH]ccc12 | HBr | null | null | null | CN1C[C@@H]2C[C@H]1CN2.Cc1ccccc1S(=O)(=O)n1ccc2c(Br)cccc21>>Cc1ccccc1S(=O)(=O)n1ccc2c([C@@]34CN[C@H](CN3C)C4)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ca781ecdb6a54777a07a8ce4c7128b30 | CCN1CCNCC1.O=S(=O)(c1ccccc1)n1ccc2c(Br)cccc21>>CCN1CCN(c2cccc3c2ccn3S(=O)(=O)c2ccccc2)CC1 | BrC1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=CC=CC=C1.C(C)N1CCNCC1>>C(C)N1CCN(CC1)C1=C2C=CN(C2=CC=C1)S(=O)(=O)C1=CC=CC=C1 | [CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][NH:6][CH2:25][CH2:26]1.Br[c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[cH:13][cH:14][n:15]2[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[cH:8][cH:9][cH:10][c:11]3[c:12]2[cH:13][cH:14][n:15]3[S:16](=[O:17])(=[O:18])[c:19]2... | CCN1CCNCC1.O=S(=O)(c1ccccc1)n1ccc2c(Br)cccc21 | CCN1CCN(c2cccc3c2ccn3S(=O)(=O)c2ccccc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 2bd3f0e7b0c672752798f8ae9143cd0c09f108cad412ec7b05ce2725693ded28 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=S(=O)(c1ccccc1)n1ccc2c(N3CCNCC3)cccc21 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6](-[#16:7]):[c:8]:[c:9]:[c:10]:2:1.[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[#16:7]-[#7;a:6]1:[c:8]:[c:9]:[c:10]2:[c:5]:1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:2-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:16]-[C:15]-1 | 48 | [{"value": 48.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared from 4-bromo-1-(benzenesulfonyl)-1H-indole and 4-ethylpiperazine according to Method 1 to afford 129 mg (48%) of a white solid: 1H NMR (CD3OD) δ 7.94–6.81 (m, 10 H), 3.69–3.62 (m, 4 H), 2.34–3.26 (partly hidden) (m, 4 H), 3.14–3.04 (m, 2 H), 1.40 (t, J=7 Hz, 3 H); MS (ESI) 370.1 (M+H)+; ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cccc2[nH]ccc12 | C1C[NH]CC[NH]1.c1cccc2[nH]ccc12 | C1C[NH]CC[NH]1.c1cccc2[nH]ccc12.c1ccccc1 | HBr | null | null | null | CCN1CCNCC1.O=S(=O)(c1ccccc1)n1ccc2c(Br)cccc21>>CCN1CCN(c2cccc3c2ccn3S(=O)(=O)c2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8008fa54facc4b4e9dcdeff3d5d00384 | Brc1ccc2[nH]ccc2c1.CC(C)[Si](Cl)(C(C)C)C(C)C>>CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(Br)ccc21 | [O-]S(=O)(=O)[O-].[Mg+2].[H-].[Na+].BrC=1C=C2C=CNC2=CC1.C(C)(C)[Si](C(C)C)(C(C)C)Cl>>BrC=1C=C2C=CN(C2=CC1)[Si](C(C)C)(C(C)C)C(C)C | [nH:11]1[cH:12][cH:13][c:14]2[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]12.Cl[Si:4]([CH:2]([CH3:1])[CH3:3])([CH:5]([CH3:6])[CH3:7])[CH:8]([CH3:9])[CH3:10]>>[CH3:1][CH:2]([CH3:3])[Si:4]([CH:5]([CH3:6])[CH3:7])([CH:8]([CH3:9])[CH3:10])[n:11]1[cH:12][cH:13][c:14]2[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]12 | Brc1ccc2[nH]ccc2c1.CC(C)[Si](Cl)(C(C)C)C(C)C | CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(Br)ccc21 | null | null | O.CN(C)C=O.C(Cl)Cl | Protection | OtherReaction | 279c1bacdf93fb106c64d785cead40315d8d0ab34370c5ee125a352a302a53c4 | f0dce65f75d702dc7e016c0abdb24b26134ae5c509e2d0da4a21967fb59ed09d | c1ccc2[nH]ccc2c1 | Cl-[Si;H0;D4;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[C:8](-[C;D1;H3:9])-[C;D1;H3:10].[c:11]:[c:12]1:[c:13]:[c:14]:[c:15]:[nH;D2;+0:16]:1>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])-[Si;H0;D4;+0:1](-[C:2](-[C;D1;H3:3])-[C;D1;H3:4])(-[C:5](-[C;D1;H3:6])-[C;D1;H3:7])-[n;H0;D3;+0:16]1:[c:15]:[c:14]... | 85 | [{"value": 85.0, "product": "BrC=1C=C2C=CN(C2=CC1)[Si](C(C)C)(C(C)C)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 5-Bromoindole (3.92 g; 20 mmol) was dissolved in DCM (100 mL) and DMF (1 mL). NaH (0.88 g, 22 mmol; 60% in oil) was added to the cooled solution. After stirring for 15 minutes, triisopropylsilyl chloride (3.86 g, 20 mmol) was added dropwise to the reaction mixture. After 3 h, water (1 mL) was added, followed by MgSO4. ... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Silyl protective group | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | HCl | O.CN(C)C=O.C(Cl)Cl | null | 0.25 | Brc1ccc2[nH]ccc2c1.CC(C)[Si](Cl)(C(C)C)C(C)C>O.CN(C)C=O.C(Cl)Cl>CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(Br)ccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d321082273d4ef781dc02b74cee9d6a | CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(Br)ccc21.CN1CCNCC1>>CN1CCN(c2ccc3[nH]ccc3c2)CC1 | BrC=1C=C2C=CN(C2=CC1)[Si](C(C)C)(C(C)C)C(C)C.CN1CCNCC1.CC(C)(C)[O-].[Na+]>>CN1CCN(CC1)C=1C=C2C=CNC2=CC1 | CC(C)[Si](C(C)C)(C(C)C)[n:10]1[c:9]2[cH:8][cH:7][c:6](Br)[cH:14][c:13]2[cH:12][cH:11]1.[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:15][CH2:16]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]3[nH:10][cH:11][cH:12][c:13]3[cH:14]2)[CH2:15][CH2:16]1 | CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(Br)ccc21.CN1CCNCC1 | CN1CCN(c2ccc3[nH]ccc3c2)CC1 | null | CC(=O)[O-].CC(=O)[O-].[Pd+2].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C | C=1(C(=CC=CC1)C)C | Heteroatom Alkylation and Arylation | OtherReaction | a4fe2e38d9325cd6286ff481b41b7116f113b6d7ad6f41036d7118f486e22175 | 922251cef8059c3b7abae2a8635a7998dd202ca1cb223b35107f237a60f4c110 | c1cc2cc(N3CCNCC3)ccc2[nH]1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[c:4]:[c:5]:[n;H0;D3;+0:6](-[Si](-C(-C)-C)(-C(-C)-C)-C(-C)-C):[c:7]:2:[c:8]:[c:9]:1.[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[#7:10]1-[C:11]-[C:12]-[N;H0;D3;+0:13](-[c;H0;D3;+0:1]2:[c:2]:[c:3]3:[c:4]:[c:5]:[nH;D2;+0:6]:[c:7]:3:[c:8]:[c:9]:2)-[C:14]-[C:15]-1 | 57 | [{"value": 57.0, "product": "CN1CCN(CC1)C=1C=C2C=CNC2=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.7, "product": "CN1CCN(CC1)C=1C=C2C=CNC2=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 5 | HOUR | 5-Bromo-1-triisopropylsilyl-indole (5.8 g, 16.4 mmol), N-methylpiperazine (1.8 g, 18 numol), NaOt-Bu (2.2 g, 23 mmol), Pd(OAc)2 (37 mg, 0.16 mmol), Pt-Bu3 (66 mg, 0.33 nmmol) and xylene (30 mL) were mixed and heated to 130° C. under stirring for 5 h. The crude material was chromatographed on a silica column using DCM/M... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine.Silyl protective group | Tertiary amine | c1ccc2[nH]ccc2c1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1 | HBr | CC(=O)[O-].CC(=O)[O-].[Pd+2].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.C=1(C(=CC=CC1)C)C | 130 | 5 | CC(C)[Si](C(C)C)(C(C)C)n1ccc2cc(Br)ccc21.CN1CCNCC1>CC(=O)[O-].CC(=O)[O-].[Pd+2].P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.C=1(C(=CC=CC1)C)C>CN1CCN(c2ccc3[nH]ccc3c2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed49fbd1fa8449b196577007bf5b1c3e | CN1CCN(c2ccc3[nH]ccc3c2)CC1.O=S(=O)(Cl)c1ccccc1>>CN1CCN(c2ccc3c(ccn3S(=O)(=O)c3ccccc3)c2)CC1 | CN1CCN(CC1)C=1C=C2C=CNC2=CC1.C1(=CC=CC=C1)S(=O)(=O)Cl.[OH-].[Na+]>>C1(=CC=CC=C1)S(=O)(=O)N1C=CC2=CC(=CC=C12)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11][cH:12][nH:13]3)[cH:23]2)[CH2:24][CH2:25]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]3[c:10]([cH:11][cH:12][n:13]3[S:14](=[O:15])(=[O:16])[c:17]3[cH:18][cH:19][cH:2... | CN1CCN(c2ccc3[nH]ccc3c2)CC1.O=S(=O)(Cl)c1ccccc1 | CN1CCN(c2ccc3c(ccn3S(=O)(=O)c3ccccc3)c2)CC1 | null | CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC.[Cl-] | C(Cl)Cl | Miscellaneous | OtherReaction | b2b0fa9a79049e6f5621e837ed4836919c6cf82dece4f60c93a30b12a3dbd400 | 5f0d826ff827e7d94d07bc9ee74d0a88c79bcf75bb024f05043486e1cbe294bd | O=S(=O)(c1ccccc1)n1ccc2cc(N3CCNCC3)ccc21 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[c:7]:[c:8]1:[c:9]:[c:10]:[c:11]:[nH;D2;+0:12]:1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[c:4](:[c:5]):[c:6])-[n;H0;D3;+0:12]1:[c:11]:[c:10]:[c:9]:[c:8]:1:[c:7] | 66 | [{"value": 66.0, "product": "C1(=CC=CC=C1)S(=O)(=O)N1C=CC2=CC(=CC=C12)N1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | 5-(4-Methylpiperazin-1-yl)-indole (215 mg, 1 mmol), benzenesulfonylchloride (265 mg, 1.5 mmol) and Aliquat 336 (10 mg) were dissolved in DCM (10 mL). Aqueous NaOH (20%, 2 mL) was added and the mixture was stirred vigorously for 6 h. The organic layer was separated, dried and concentrated to give the crude as an oil tha... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | C1C[NH]CC[NH]1.c1ccc2[nH]ccc2c1.c1ccccc1 | HCl | CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC.[Cl-].C(Cl)Cl | null | 6 | CN1CCN(c2ccc3[nH]ccc3c2)CC1.O=S(=O)(Cl)c1ccccc1>CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC.[Cl-].C(Cl)Cl>CN1CCN(c2ccc3c(ccn3S(=O)(=O)c3ccccc3)c2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6b2a56a0275840ea9924f474c1ec4f3d | COc1ccc(S(=O)(=O)n2ccc3cc(N4CCN(Cc5ccccc5)CC4)ccc32)cc1.ClCCl>>COc1ccc(S(=O)(=O)n2ccc3cc(N4CCNCC4)ccc32)cc1.Cl | COC1=CC=C(C=C1)S(=O)(=O)N1C=CC2=CC(=CC=C12)N1CCN(CC1)CC1=CC=CC=C1.C(Cl)Cl>>Cl.COC1=CC=C(C=C1)S(=O)(=O)N1C=CC2=CC(=CC=C12)N1CCNCC1 | c1ccc(C[N:19]2[CH2:18][CH2:17][N:16]([c:15]3[cH:14][c:13]4[cH:12][cH:11][n:10]([S:7]([c:6]5[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:26][cH:25]5)(=[O:8])=[O:9])[c:24]4[cH:23][cH:22]3)[CH2:21][CH2:20]2)cc1.ClC[Cl:27]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[n:10]2[cH:11][cH:12][c:13]3[cH:14][c:15]([N:16]4[CH2... | COc1ccc(S(=O)(=O)n2ccc3cc(N4CCN(Cc5ccccc5)CC4)ccc32)cc1.ClCCl | COc1ccc(S(=O)(=O)n2ccc3cc(N4CCNCC4)ccc32)cc1.Cl | null | null | null | Miscellaneous | OtherReaction | 219d8a9b9b7d68c72b8335df9a0598f7711239a8d4931603f9b986d05e0b7640 | 72096763e12909968ae463c1f826bfac3cb3bc06124d61804b8299d531b1571f | O=S(=O)(c1ccccc1)n1ccc2cc(N3CCNCC3)ccc21 | C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1)-c1:c:c:c:c:c:1.Cl-C-[Cl;H0;D1;+0:7]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[ClH;D0;+0:7] | null | [] | null | null | 2 | HOUR | N-(4-Methoxybenzenesulfonyl)-5-(4-benzylpiperazin-1-yl)-indole (0.25 g, 0.54 mmol) was dissolved in DCM (4 mL), a-chloroethyl chlorofonnate (0.150 g, 1.05 mmol) was added and the mixture left at room temperature for 2 h after which it was concentrated. MeOH (10 mL) was added and the mixture refluxed for 2 hrs and then ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Tertiary amine | Secondary amine | c1ccccc1.C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.c1ccc2[nH]ccc2c1.C1C[NH]CCN1 | HCl | null | null | 2 | COc1ccc(S(=O)(=O)n2ccc3cc(N4CCN(Cc5ccccc5)CC4)ccc32)cc1.ClCCl>>COc1ccc(S(=O)(=O)n2ccc3cc(N4CCNCC4)ccc32)cc1.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5f7ad1a822044384bf271b2d527fe775 | CC(C)(C)OC(=O)N1CCN(c2cccc3c2ccn3S(=O)(=O)c2ccccc2)CC1.II>>CC(C)(C)OC(=O)N1CCN(c2cccc3c2cc(I)n3S(=O)(=O)c2ccccc2)CC1 | C(CCC)[Mg]Cl.C(C)(C)NC(C)C.II.C1(=CC=CC=C1)S(=O)(=O)N1C=CC2=C(C=CC=C12)N1CCN(CC1)C(=O)OC(C)(C)C>>IC=1N(C2=CC=CC(=C2C1)N1CCN(CC1)C(=O)OC(C)(C)C)S(=O)(=O)C1=CC=CC=C1 | [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]2[cH:13][cH:14][cH:15][c:16]3[c:17]2[cH:18][cH:19][n:21]3[S:22](=[O:23])(=[O:24])[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[CH2:31][CH2:32]1.I[I:20]>>[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]2[cH... | CC(C)(C)OC(=O)N1CCN(c2cccc3c2ccn3S(=O)(=O)c2ccccc2)CC1.II | CC(C)(C)OC(=O)N1CCN(c2cccc3c2cc(I)n3S(=O)(=O)c2ccccc2)CC1 | null | null | C1CCOC1 | Functional Group Interconversion | OtherReaction | 9a5ab3d57cb6847f85ea8e60c046da965c324287562359aa5cdf7fd03f2812d2 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=S(=O)(c1ccccc1)n1ccc2c(N3CCNCC3)cccc21 | I-[I;H0;D1;+0:1].[#16:2]-[#7;a:3]1:[c:4]:[c:5]:[c:6]:[cH;D2;+0:7]:1>>[#16:2]-[#7;a:3]1:[c:4]:[c:5]:[c:6]:[c;H0;D3;+0:7]:1-[I;H0;D1;+0:1] | null | [] | null | null | 4 | HOUR | A mixture of butylmagnesium chloride (1 mL, Immol, 2.0 M in ether) and di-isopropyl amine (0.279 mL, 2 mmol) in dry THF (5 mL) was stirred for 4 h under inert atmosphere at room temperature. A solution of tert-butyl 4-[1-(phenylsulfonyl)-1H-indol-4-yl]-1-piperazinecarboxylate (220 mg, 0.5 mmol) in THF (2 mL) was added ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cccc2[nH]ccc12 | c1cc2ccccc2[nH]1 | C1C[NH]CC[NH]1.c1cc2ccccc2[nH]1.c1ccccc1 | HI | C1CCOC1 | null | 4 | CC(C)(C)OC(=O)N1CCN(c2cccc3c2ccn3S(=O)(=O)c2ccccc2)CC1.II>C1CCOC1>CC(C)(C)OC(=O)N1CCN(c2cccc3c2cc(I)n3S(=O)(=O)c2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-126fbc52cb0b4e498ab0321d2c86dc56 | CC(C)(C)OC(=O)N1CCN(c2cccc3c2cc(I)n3S(=O)(=O)c2ccccc2)CC1.OB(O)c1ccccc1>>CC(C)(C)OC(=O)N1CCN(c2cccc3c2cc(-c2ccccc2)n3S(=O)(=O)c2ccccc2)CC1 | IC=1N(C2=CC=CC(=C2C1)N1CCN(CC1)C(=O)OC(C)(C)C)S(=O)(=O)C1=CC=CC=C1.C1(=CC=CC=C1)B(O)O.C(=O)([O-])[O-].[K+].[K+]>>C1(=CC=CC=C1)C=1N(C2=CC=CC(=C2C1)N1CCN(CC1)C(=O)OC(C)(C)C)S(=O)(=O)C1=CC=CC=C1 | I[c:19]1[cH:18][c:17]2[c:12]([N:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:37][CH2:36]3)[cH:13][cH:14][cH:15][c:16]2[n:26]1[S:27](=[O:28])(=[O:29])[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1.OB(O)[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[... | CC(C)(C)OC(=O)N1CCN(c2cccc3c2cc(I)n3S(=O)(=O)c2ccccc2)CC1.OB(O)c1ccccc1 | CC(C)(C)OC(=O)N1CCN(c2cccc3c2cc(-c2ccccc2)n3S(=O)(=O)c2ccccc2)CC1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C(OC)COC | C-C Coupling | Suzuki coupling with boronic acids | 3b8f3e0259b4769a5826e874d5636520024cfb748a43924162932bbdf29a40ad | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=S(=O)(c1ccccc1)n1c(-c2ccccc2)cc2c(N3CCNCC3)cccc21 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:1-[#16:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[#16:6]-[#7;a:5]1:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11] | null | [] | null | null | null | null | tert-Butyl 4-[2-iodo-1-(phenylsulfonyl)-1H-indol-4-yl]-1-piperazinecarboxylate(40 mg, 0.07 mmol), phenyl boronic acid (12 mg, 0.1 mmol), Pd(PPh3)4 (2 mg, 0.002 mmol) and a 2M aqueous solution of K2CO3 (0.075 mL) were stirred for 3 days at 80° C. in dimethoxyethane (2 mL). After evaporation of the solvent, the crude was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2ccccc2[nH]1.c1ccccc1 | c1cc2ccccc2[nH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1cc2ccccc2[nH]1.c1ccccc1.c1ccccc1 | HI.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C(OC)COC | null | null | CC(C)(C)OC(=O)N1CCN(c2cccc3c2cc(I)n3S(=O)(=O)c2ccccc2)CC1.OB(O)c1ccccc1>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.C(OC)COC>CC(C)(C)OC(=O)N1CCN(c2cccc3c2cc(-c2ccccc2)n3S(=O)(=O)c2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0935eb894ecc468c996ee9c9067d7403 | CC(C)(C)OC(=O)N1CCN(c2cccc3c2cc(-c2ccccc2)n3S(=O)(=O)c2ccccc2)CC1>>O=S(=O)(c1ccccc1)n1c(-c2ccccc2)cc2c(N3CCNCC3)cccc21 | C1(=CC=CC=C1)C=1N(C2=CC=CC(=C2C1)N1CCN(CC1)C(=O)OC(C)(C)C)S(=O)(=O)C1=CC=CC=C1.Cl>>Cl.C1(=CC=CC=C1)C=1N(C2=CC=CC(=C2C1)N1CCNCC1)S(=O)(=O)C1=CC=CC=C1 | CC(C)(C)OC(=O)[N:25]1[CH2:24][CH2:23][N:22]([c:21]2[c:20]3[cH:19][c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][cH:18]4)[n:11]([S:3](=[O:2])(=[O:4])[c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[c:31]3[cH:30][cH:29][cH:28]2)[CH2:27][CH2:26]1>>[O:2]=[S:3](=[O:4])([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[n:11]1[c:12](-[c:13]2[cH:14... | CC(C)(C)OC(=O)N1CCN(c2cccc3c2cc(-c2ccccc2)n3S(=O)(=O)c2ccccc2)CC1 | O=S(=O)(c1ccccc1)n1c(-c2ccccc2)cc2c(N3CCNCC3)cccc21 | null | null | CCOCC.C(Cl)Cl | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=S(=O)(c1ccccc1)n1c(-c2ccccc2)cc2c(N3CCNCC3)cccc21 | 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 | 2 | HOUR | tert-Butyl 4-[2-phenyl-1-(phenylsulfonyl)-1H-indol-4-yl]-1-piperazinecarboxylate (30 mg, 0.058 mmol) was dissolved in CH2Cl2 (1 mL) followed by addition of HCl in ether (1 mL). The reaction was shaken for 2 h at room temperature. The resulting precipitate was filtered off and washed with ether giving 20 mg of the desir... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.c1ccccc1.C1C[NH]CCN1.c1cc2ccccc2[nH]1 | HO- | CCOCC.C(Cl)Cl | null | 2 | CC(C)(C)OC(=O)N1CCN(c2cccc3c2cc(-c2ccccc2)n3S(=O)(=O)c2ccccc2)CC1>CCOCC.C(Cl)Cl>O=S(=O)(c1ccccc1)n1c(-c2ccccc2)cc2c(N3CCNCC3)cccc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-47a2ac6edb95468782048df6afee6428 | CCCCC1OC1COCC1OC1CCCC.Oc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1>>CCCCOCC(O)COc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 | C(CCC)C1C(COCC2C(CCCC)O2)O1.C1(=CC=CC2=CC=CC=C12)C1=C(C(=NN=N1)C1=C(C=C(C=C1)O)O)C1=CC=CC2=CC=CC=C12>>C1(=CC=CC2=CC=CC=C12)C1=C(C(=NN=N1)C1=C(C=C(C=C1)OCC(COCCCC)O)O)C1=CC=CC2=CC=CC=C12 | CCCCC1OC1[CH2:6][O:5][CH2:9][CH:7]1C([CH2:4][CH2:3][CH2:2][CH3:1])[O:8]1.[OH:10][c:11]1[cH:12][cH:13][c:14](-[c:15]2[n:16][n:17][n:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][c:24]4[cH:25][cH:26][cH:27][cH:28][c:29]34)[c:30]2-[c:31]2[cH:32][cH:33][cH:34][c:35]3[cH:36][cH:37][cH:38][cH:39][c:40]23)[c:41]([OH:42])[cH:43]1>>[... | CCCCC1OC1COCC1OC1CCCC.Oc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 | CCCCOCC(O)COc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 | null | [Br-].C(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 | C=1(C(=CC=CC1)C)C | Heteroatom Alkylation and Arylation | OtherReaction | 1284ad66a826e7d61792c06884b39028c70c990f357632fee5aaf7aa6734b38e | 8b15a186b171fde78b34460cf24368895f124a088810c2bdaa76ac96db4167da | c1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)cc1 | C-C-C-C-C1-O-C-1-[CH2;D2;+0:1]-[O;H0;D2;+0:2]-[CH2;D2;+0:3]-[CH;D3;+0:4]1-[O;H0;D2;+0:5]-C-1-[CH2;D2;+0:6]-[C:7]-[C:8].[OH;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[C:8]-[C:7]-[CH2;D2;+0:6]-[O;H0;D2;+0:2]-[CH2;D2;+0:1]-[CH;D3;+0:4](-[OH;D1;+0:5])-[CH2;D2;+0:3]-[O;H0;D2;+0:9]-[c:10](:[c:11]):[c:12] | null | [] | 25 | CELSIUS | 18 | HOUR | 6.60 g of butyl-2,3-epoxypropyl ether and 0.78 g of ethyl-triphenyl-phosphonium bromide are added to a solution of 20.0 g of the product from Example A6 in 200 ml of xylene. That reaction mixture is heated to boiling for 18 h. 0.5 g of activated carbon is then added to the reaction mixture and the resulting mixture is ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Aromatic alcohol | Ether.Ether.Secondary alcohol | C1CO1.C1CO1 | null | c1ccccc1.c1cnnnc1.c1ccc2ccccc2c1.c1ccc2ccccc2c1 | HO- | [Br-].C(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C=1(C(=CC=CC1)C)C | 25 | 18 | CCCCC1OC1COCC1OC1CCCC.Oc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1>[Br-].C(C)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C=1(C(=CC=CC1)C)C>CCCCOCC(O)COc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-692c51953fd446438dbb2938ec9d651f | CCOC(=O)C(C)Br.Oc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1>>CCOC(=O)C(C)Oc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 | C([O-])([O-])=O.[K+].[K+].C(C)OC(C(C)Br)=O.C1(=CC=CC2=CC=CC=C12)C1=C(C(=NN=N1)C1=C(C=C(C=C1)O)O)C1=CC=CC2=CC=CC=C12>>C1(=CC=CC2=CC=CC=C12)C1=C(C(=NN=N1)C1=C(C=C(C=C1)OC(C)C(=O)OCC)O)C1=CC=CC2=CC=CC=C12 | Br[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7].[OH:8][c:9]1[cH:10][cH:11][c:12](-[c:13]2[n:14][n:15][n:16][c:17](-[c:18]3[cH:19][cH:20][cH:21][c:22]4[cH:23][cH:24][cH:25][cH:26][c:27]34)[c:28]2-[c:29]2[cH:30][cH:31][cH:32][c:33]3[cH:34][cH:35][cH:36][cH:37][c:38]23)[c:39]([OH:40])[cH:41]1>>[CH3:1][CH2:2][O:3][C:4](=... | CCOC(=O)C(C)Br.Oc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 | CCOC(=O)C(C)Oc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a60236748d2543bdb97e5465447a595cd9bb5fef4e3fe96ed6af652af51cd157 | 94a54f0a6e629a85ca32b8fd3cf243ab64283e31ecfe8705ffe0df2304c488b4 | c1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)cc1 | Br-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | 125 | CELSIUS | null | null | 9.39 g of potassium carbonate and 9.02 g of 2-bromopropionic acid ethyl ester are added to a solution of 20.0 g of the product from Example A6 in 200 ml of DMF. The reaction mixture is heated at 125° C. for 3.5 h. The solid which precipitates is filtered off and washed with toluene. The combined organic phase is freed ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.c1cnnnc1.c1ccc2ccccc2c1.c1ccc2ccccc2c1 | HBr | CN(C)C=O | 125 | null | CCOC(=O)C(C)Br.Oc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1>CN(C)C=O>CCOC(=O)C(C)Oc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5ff40fbc24cd473c904d9efe22b51f9b | O=C1OCCO1.Oc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1>>OCCOc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 | C([O-])([O-])=O.[K+].[K+].C1(OCCO1)=O.C1(=CC=CC2=CC=CC=C12)C1=C(C(=NN=N1)C1=C(C=C(C=C1)O)O)C1=CC=CC2=CC=CC=C12>>C1(=CC=CC2=CC=CC=C12)C1=C(C(=NN=N1)C1=C(C=C(C=C1)OCCO)O)C1=CC=CC2=CC=CC=C12 | O=C1O[CH2:3][CH2:2][O:1]1.[OH:4][c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][n:11][n:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][c:18]4[cH:19][cH:20][cH:21][cH:22][c:23]34)[c:24]2-[c:25]2[cH:26][cH:27][cH:28][c:29]3[cH:30][cH:31][cH:32][cH:33][c:34]23)[c:35]([OH:36])[cH:37]1>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8](-[c:9... | O=C1OCCO1.Oc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 | OCCOc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 34950df4dc1bc6c778d9cfa26c728e443e4886f7382a4283f1fbae4a959b8c37 | c6f5c5ba2d936b513bc18d6bcb095f40591aa3ba8700a9f5b8ecbbdd690dab72 | c1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)cc1 | O=C1-O-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[OH;D1;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 140 | CELSIUS | null | null | 9.39 g of potassium carbonate and 4.39 g of ethylene carbonate are added to 20 g of the product from Example A6 in 200 ml of anhydrous DMF. The reaction mixture is heated at 140° C. for 18 h. The salts which precipitate are filtered off and washed with toluene. The combined organic phase is freed of solvent in vac. and... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Aromatic alcohol | Ether.Primary alcohol | C1COCO1 | null | c1ccccc1.c1cnnnc1.c1ccc2ccccc2c1.c1ccc2ccccc2c1 | Other | CN(C)C=O | 140 | null | O=C1OCCO1.Oc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1>CN(C)C=O>OCCOc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-32bf5b9791c7448ca1a7e797c6eb1088 | CC(=O)OC(C)=O.OCCOc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1>>CC(=O)OCCOc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 | C(C)(=O)OC(C)=O.C(C)N(CC)CC.CN(C)C1=NC=CC=C1.C1(=CC=CC2=CC=CC=C12)C1=C(C(=NN=N1)C1=C(C=C(C=C1)OCCO)O)C1=CC=CC2=CC=CC=C12>>C1(=CC=CC2=CC=CC=C12)C1=C(C(=NN=N1)C1=C(C=C(C=C1)OCCOC(C)=O)O)C1=CC=CC2=CC=CC=C12 | CC(=O)O[C:2]([CH3:1])=[O:3].[OH:4][CH2:5][CH2:6][O:7][c:8]1[cH:9][cH:10][c:11](-[c:12]2[n:13][n:14][n:15][c:16](-[c:17]3[cH:18][cH:19][cH:20][c:21]4[cH:22][cH:23][cH:24][cH:25][c:26]34)[c:27]2-[c:28]2[cH:29][cH:30][cH:31][c:32]3[cH:33][cH:34][cH:35][cH:36][c:37]23)[c:38]([OH:39])[cH:40]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:... | CC(=O)OC(C)=O.OCCOc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 | CC(=O)OCCOc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 | null | null | ClCCl | Acylation | Transesterification | f81e513b7b512b10157c16426844efd8d88e34c97987c1347c6ba8a688351205 | fc27d67c790d5fb520ba5d49de1490661fa5b822b714863734ce7e3029dfa84f | c1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5]-[OH;D1;+0:6]>>[C:4]-[C:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | null | null | 9.11 g of acetic anhydride, 18.1 g of triethylamine and 0.73 g of dimethylaminopyridine in 400 ml of anhydrous dichloromethane are added to the product from Example A9. The reaction mixture is heated to boiling. When the reaction is complete (monitoring by TLC), the solvent is removed in vac. and the residue is taken u... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol | Ester | null | null | c1ccccc1.c1cnnnc1.c1ccc2ccccc2c1.c1ccc2ccccc2c1 | HO- | ClCCl | null | null | CC(=O)OC(C)=O.OCCOc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1>ClCCl>CC(=O)OCCOc1ccc(-c2nnnc(-c3cccc4ccccc34)c2-c2cccc3ccccc23)c(O)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d113d1d13d1a417184600b4984e0e239 | CCOC(=O)CC(=O)c1ccccc1.CCOc1ccc2cc(C=O)c(Cl)nc2c1>>COc1ccc2cc(C(=O)O)c(-c3ccccc3)nc2c1 | C(C)OC(CC(C1=CC=CC=C1)=O)=O.ClC1=NC2=CC(=CC=C2C=C1C=O)OCC>>COC1=CC=C2C=C(C(=NC2=C1)C1=CC=CC=C1)C(=O)O | CCOC(CC(=O)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)=[O:10].C[CH2:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([CH:9]=[O:11])[c:12](Cl)[n:19][c:20]2[cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[n:19][c:20]2[cH:21]1 | CCOC(=O)CC(=O)c1ccccc1.CCOc1ccc2cc(C=O)c(Cl)nc2c1 | COc1ccc2cc(C(=O)O)c(-c3ccccc3)nc2c1 | null | null | null | C-C Coupling | OtherReaction | 7c32ce38a4e5a74c4a0618cbab27c8441499665a341484a6269105a706875c37 | 93b229beb20920ec85cc9e2c59882edfa4d0e5f2424e56e03aec0836f457e5a0 | c1ccc(-c2ccc3ccccc3n2)cc1 | C-C-O-C(=[O;H0;D1;+0:1])-C-C(=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].C-[CH2;D2;+0:7]-[#8:8]-[c:9].Cl-[c;H0;D3;+0:10](:[#7;a:11]:[c:12]):[c:13](-[CH;D2;+0:14]=[O;H0;D1;+0:15]):[c:16]>>[CH3;D1;+0:7]-[#8:8]-[c:9].[O;H0;D1;+0:1]=[C;H0;D3;+0:14](-[OH;D1;+0:15])-[c:13](:[c:16]):[c;H0;D3;+0:10](-[c;H0;D3;+0:2](:[c:3]:[c:... | null | [] | null | null | null | null | Following the procedure of Example 36 (a)-(b) substituting ethylbenzoylacetate in step 36 (a) gave the above named compound. LCMS m/e [M+H]+=280.2
Conditions: See reaction.notes.procedure_details.
Workup: gave the | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde.Ketone.Ester.Ether | Carboxylic acid.Ether | c1ccccc1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1 | c1ccc2ncccc2c1.c1ccccc1 | HCl | null | null | null | CCOC(=O)CC(=O)c1ccccc1.CCOc1ccc2cc(C=O)c(Cl)nc2c1>>COc1ccc2cc(C(=O)O)c(-c3ccccc3)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8178b2b12697448ba91a6d555ccc7cb6 | CCN(C(C)C)C(C)C.CN(C)C=O.Nc1nc2ccccc2s1.O.O.c1ccncc1>>COc1ccc(N2CCOCC2)c2sc(NC(=O)c3ccnc(C)c3)nc12 | N1=CC=CC=C1.C(C)N(C(C)C)C(C)C.C(C(=O)Cl)(=O)Cl.NC=1SC2=C(N1)C=CC=C2.O.O.CN(C=O)C>>COC1=CC=C(C2=C1N=C(S2)NC(C2=CC(=NC=C2)C)=O)N2CCOCC2 | CC(C)[N:7]([CH:8](C)[CH3:9])[CH2:12][CH3:11].N([CH3:1])([CH:17]=[O:18])[CH3:24].[cH:3]1[cH:4][cH:5][cH:6][c:13]2[s:14][c:15]([NH2:16])[n:26][c:27]12.[OH2:2].[OH2:10].[cH:19]1[cH:20][cH:21][n:22][cH:23][cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[c:13]2[s:14][c:15]([NH:16][C... | CCN(C(C)C)C(C)C.CN(C)C=O.Nc1nc2ccccc2s1.O.O.c1ccncc1 | COc1ccc(N2CCOCC2)c2sc(NC(=O)c3ccnc(C)c3)nc12 | null | null | ClCCl | Acylation | OtherReaction | b08f9aa46f1770b44cd84d03ef101ac678522b800e2f06d35c445fa16f8b39c4 | a877756ff5419759c03e5250cdd4887729a56ef6e2c3602d08749a2de0da2361 | O=C(Nc1nc2cccc(N3CCOCC3)c2s1)c1ccncc1 | C-C(-C)-[N;H0;D3;+0:1](-[C:2]-[CH3;D1;+0:3])-[CH;D3;+0:4](-C)-[CH3;D1;+0:5].[#7;a:6]1:[c:7]:[c:8]:[cH;D2;+0:9]:[c:10]:[cH;D2;+0:11]:1.[CH3;D1;+0:12]-N(-[CH3;D1;+0:13])-[CH;D2;+0:14]=[O;D1;H0:15].[NH2;D1;+0:16]-[c:17]1:[#16;a:18]:[c:19]2:[cH;D2;+0:20]:[c:21]:[c:22]:[cH;D2;+0:23]:[c:24]:2:[#7;a:25]:1.[OH2;D0;+0:26].[OH2;... | null | [] | null | null | 0.2 | HOUR | 20.0 g Pyridine acid (115 mmol) were suspended at RT in 100 ml dichloromethane. 0.5 ml Dimethylformamide (6.5 mmol) was added, and after 0.2 h, 14.9 g oxalyl chloride (10.2 ml, 115 mmol) were added over 2 min. The dropping funnel was rinsed with 4 ml dichloromethane. The brown suspension was stirred at RT for 3 h. Then... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Primary amine.Tertiary amine | Ether.Ether.Secondary amide.Tertiary amine | c1ccc2scnc2c1.c1ccncc1 | C1COCC[NH]1.c1ccc2scnc2c1.c1ccncc1 | C1COCC[NH]1.c1ccc2scnc2c1.c1ccncc1 | Other | ClCCl | null | 0.2 | CCN(C(C)C)C(C)C.CN(C)C=O.Nc1nc2ccccc2s1.O.O.c1ccncc1>ClCCl>COc1ccc(N2CCOCC2)c2sc(NC(=O)c3ccnc(C)c3)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a6aafb44c9c446da727d1d1bc6b81be | COc1ccc(NC(C)=O)cc1NC(=S)NC(=O)c1ccccc1>>COc1ccc(NC(C)=O)c2sc(NC(=O)c3ccccc3)nc12 | CS(=O)C.Br.C(C1=CC=CC=C1)(=O)NC(NC=1C=C(C=CC1OC)NC(C)=O)=S>>C(C)(=O)NC1=CC=C(C=2N=C(SC21)NC(C2=CC=CC=C2)=O)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8]([CH3:9])=[O:10])[cH:11][c:24]1[NH:23][C:13](=[S:12])[NH:14][C:15](=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][C:8]([CH3:9])=[O:10])[c:11]2[s:12][c:13]([NH:14][C:15](=[O:16])[c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[n:... | COc1ccc(NC(C)=O)cc1NC(=S)NC(=O)c1ccccc1 | COc1ccc(NC(C)=O)c2sc(NC(=O)c3ccccc3)nc12 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 9fc354848fb2fb52ac9a677ec08efbe70faac27defb4ee4a070dc3814d93a73c | 01ff041a21adca51a94f69a62115e81e604cce12edd47d529ec3eedb88c39f4c | O=C(Nc1nc2ccccc2s1)c1ccccc1 | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8](-[NH;D2;+0:9]-[C;H0;D3;+0:10](=[S;H0;D1;+0:11])-[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]):[c:16]>>[C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#7:4]-[c:5](:[c:6]):[c;H0;D3;+0:7]1:[s;H0;D2;+0:11]:[c;H0;D3;+0:10](-[#7:12]-[C:13](=[O;D1;H0:14])-[c:15]):[n;H0;D2;+0:9]... | 86 | [{"value": 86.0, "product": "C(C)(=O)NC1=CC=C(C=2N=C(SC21)NC(C2=CC=CC=C2)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.8, "product": "C(C)(=O)NC1=CC=C(C=2N=C(SC21)NC(C2=CC=CC=C2)=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 1.5 | HOUR | To a suspension of 15.0 g (43.7 mmol) N-[3-(3-benzoyl-thioureido)-4-methoxy-phenyl]-acetamide in 200 ml glacial acetic acid was added 7.65 ml (43.6 mmol) of a 5.7 M solution of HBr in acetic acid, and the mixture was heated at 90° C. for 1 h. 2.5 ml (48.0 mmol) DMSO was then added, and stirring continued at 90° C. for ... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea | null | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1.c1ccccc1 | null | C(C)(=O)O | 90 | 1.5 | COc1ccc(NC(C)=O)cc1NC(=S)NC(=O)c1ccccc1>C(C)(=O)O>COc1ccc(NC(C)=O)c2sc(NC(=O)c3ccccc3)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d179064351194b43a86982c843ec674b | COc1ccc(N2CCN(C)C(=O)C2)cc1NC(N)=S>>COc1ccc(N2CCN(C)C(=O)C2)c2sc(N)nc12 | COC1=C(C=C(C=C1)N1CC(N(CC1)C)=O)NC(=S)N.Br.CC(=O)O.CS(=O)C>>NC=1SC2=C(N1)C(=CC=C2N2CC(N(CC2)C)=O)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH3:11])[C:12](=[O:13])[CH2:14]2)[cH:15][c:20]1[NH:19][C:17](=[S:16])[NH2:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH3:11])[C:12](=[O:13])[CH2:14]2)[c:15]2[s:16][c:17]([NH2:18])[n:19][c:20]12 | COc1ccc(N2CCN(C)C(=O)C2)cc1NC(N)=S | COc1ccc(N2CCN(C)C(=O)C2)c2sc(N)nc12 | null | null | CC(=O)O | Aromatic Heterocycle Formation | OtherReaction | 9fc354848fb2fb52ac9a677ec08efbe70faac27defb4ee4a070dc3814d93a73c | 01ff041a21adca51a94f69a62115e81e604cce12edd47d529ec3eedb88c39f4c | O=C1CN(c2cccc3ncsc23)CCN1 | [#7:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](-[N;D1;H2:8])=[S;H0;D1;+0:9]):[c:10]>>[#7:1]-[c:2](:[c:3]):[c;H0;D3;+0:4]1:[s;H0;D2;+0:9]:[c;H0;D3;+0:7](-[N;D1;H2:8]):[n;H0;D2;+0:6]:[c:5]:1:[c:10] | null | [] | null | null | null | null | From [2-methoxy-5-(4-methyl-3-oxo-piperazin-1-yl)-phenyl]-thiourea with HBr—AcOH (4 equiv.) and DMSO (2.4 equiv.) in AcOH. ES-MS m/e (%): 293 (M+H+, 100).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Thiourea | null | c1ccccc1 | c1ccc2scnc2c1 | C1C[NH]CC[NH]1.c1ccc2scnc2c1 | null | CC(=O)O | null | null | COc1ccc(N2CCN(C)C(=O)C2)cc1NC(N)=S>CC(=O)O>COc1ccc(N2CCN(C)C(=O)C2)c2sc(N)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-81cf14fa4bba449a837dcc91caaa551b | COc1ccc(N(Cc2ccc(C)cc2)Cc2ccc(C)cc2)cc1NC(=S)NC(=O)c1ccccc1>>COc1ccc(N(Cc2ccc(C)cc2)Cc2ccc(C)cc2)c2sc(NC(=O)c3ccccc3)nc12 | C(C1=CC=CC=C1)(=O)NC(=S)NC1=C(C=CC(=C1)N(CC1=CC=C(C=C1)C)CC1=CC=C(C=C1)C)OC.Br.CC(=O)O.CS(=O)C>>CC1=CC=C(CN(C2=CC=C(C=3N=C(SC32)NC(C3=CC=CC=C3)=O)OC)CC3=CC=C(C=C3)C)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH2:8][c:9]2[cH:10][cH:11][c:12]([CH3:13])[cH:14][cH:15]2)[CH2:16][c:17]2[cH:18][cH:19][c:20]([CH3:21])[cH:22][cH:23]2)[cH:24][c:37]1[NH:36][C:26](=[S:25])[NH:27][C:28](=[O:29])[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH2:8][c:9]2... | COc1ccc(N(Cc2ccc(C)cc2)Cc2ccc(C)cc2)cc1NC(=S)NC(=O)c1ccccc1 | COc1ccc(N(Cc2ccc(C)cc2)Cc2ccc(C)cc2)c2sc(NC(=O)c3ccccc3)nc12 | null | null | CC(=O)O | Aromatic Heterocycle Formation | OtherReaction | 9fc354848fb2fb52ac9a677ec08efbe70faac27defb4ee4a070dc3814d93a73c | 01ff041a21adca51a94f69a62115e81e604cce12edd47d529ec3eedb88c39f4c | O=C(Nc1nc2cccc(N(Cc3ccccc3)Cc3ccccc3)c2s1)c1ccccc1 | [#7:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[S;H0;D1;+0:8])-[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]):[c:13]>>[#7:1]-[c:2](:[c:3]):[c;H0;D3;+0:4]1:[s;H0;D2;+0:8]:[c;H0;D3;+0:7](-[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]):[n;H0;D2;+0:6]:[c:5]:1:[c:13] | null | [] | null | null | null | null | From 1-benzoyl-3-{5-[bis-(4-methyl-benzyl)-amino]-2-methoxy-phenyl}-thiourea with HBr—AcOH (2 equiv.) and DMSO (1.1 equiv.) in AcOH. ES-MS m/e (%): 508 (M+H+, 100).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Thiourea | null | c1ccccc1 | c1ccc2scnc2c1 | c1ccccc1.c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | null | CC(=O)O | null | null | COc1ccc(N(Cc2ccc(C)cc2)Cc2ccc(C)cc2)cc1NC(=S)NC(=O)c1ccccc1>CC(=O)O>COc1ccc(N(Cc2ccc(C)cc2)Cc2ccc(C)cc2)c2sc(NC(=O)c3ccccc3)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-225d37cb45ef48c3874c2173b78719eb | COCCN(C)c1ccc(OC)c(NC(N)=S)c1>>COCCN(C)c1ccc(OC)c2nc(N)sc12 | COC1=C(C=C(C=C1)N(C)CCOC)NC(=S)N.Br.CC(=O)O.CS(=O)C>>COC1=CC=C(C2=C1N=C(S2)N)N(C)CCOC | [CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:6])[c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[c:13]([NH:14][C:15]([NH2:16])=[S:17])[cH:18]1>>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:6])[c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[c:13]2[n:14][c:15]([NH2:16])[s:17][c:18]12 | COCCN(C)c1ccc(OC)c(NC(N)=S)c1 | COCCN(C)c1ccc(OC)c2nc(N)sc12 | null | null | CC(=O)O | Aromatic Heterocycle Formation | OtherReaction | 9fc354848fb2fb52ac9a677ec08efbe70faac27defb4ee4a070dc3814d93a73c | 01ff041a21adca51a94f69a62115e81e604cce12edd47d529ec3eedb88c39f4c | c1ccc2scnc2c1 | [#7:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5](-[NH;D2;+0:6]-[C;H0;D3;+0:7](-[N;D1;H2:8])=[S;H0;D1;+0:9]):[c:10]>>[#7:1]-[c:2](:[c:3]):[c;H0;D3;+0:4]1:[s;H0;D2;+0:9]:[c;H0;D3;+0:7](-[N;D1;H2:8]):[n;H0;D2;+0:6]:[c:5]:1:[c:10] | null | [] | null | null | null | null | From {2-methoxy-5-[(2-methoxy-ethyl)-methyl-amino]-phenyl}-thiourea with HBr—AcOH (2 equiv.) and DMSO (1.1 equiv.) in AcOH. ES-MS m/e (%): 268 (M+H+, 100).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Thiourea | null | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | null | CC(=O)O | null | null | COCCN(C)c1ccc(OC)c(NC(N)=S)c1>CC(=O)O>COCCN(C)c1ccc(OC)c2nc(N)sc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c38c04a2ff54f61871a1c6ab0095848 | Cc1ccc(NC(N)=S)cc1>>Cc1ccc2nc(N)sc2c1 | CS(=O)C.CC1=CC=C(C=C1)NC(=S)N.CC(=O)O.Br.CC(=O)O>>NC=1SC2=C(N1)C=CC(=C2)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7]([NH2:8])=[S:9])[cH:10][cH:11]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([NH2:8])[s:9][c:10]2[cH:11]1 | Cc1ccc(NC(N)=S)cc1 | Cc1ccc2nc(N)sc2c1 | null | null | CCOC(=O)C | Aromatic Heterocycle Formation | OtherReaction | 9fc354848fb2fb52ac9a677ec08efbe70faac27defb4ee4a070dc3814d93a73c | 01ff041a21adca51a94f69a62115e81e604cce12edd47d529ec3eedb88c39f4c | c1ccc2scnc2c1 | [N;D1;H2:1]-[C;H0;D3;+0:2](=[S;H0;D1;+0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[N;D1;H2:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:4]:[c:5](:[c:6]):[c;H0;D3;+0:7](:[c:8]:[c:9]):[s;H0;D2;+0:3]:1 | 67 | [{"value": 67.0, "product": "NC=1SC2=C(N1)C=CC(=C2)C", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 1 | HOUR | (4-Methylphenyl)thiourea (2 mmol) was added to AcOH (4 ml), and the suspension was heated to 80° C. To the solution formed was added 33% HBr in AcOH (4 mmol) followed by DMSO (2.1 mmol). After stirring at 80° C. for 1 h, the reaction mixture was cooled to 50° C., diluted with EtOAc (10 ml) and filtered. The product (as... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea | null | c1ccccc1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | null | CCOC(=O)C | 80 | 1 | Cc1ccc(NC(N)=S)cc1>CCOC(=O)C>Cc1ccc2nc(N)sc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-338e450e2b7f4467853415ac44b79a17 | CC(=O)c1ccc(O)cc1.ClCCCBr>>CC(=O)c1ccc(OCCCCl)cc1 | OC1=CC=C(C=C1)C(C)=O.BrCCCCl.C([O-])([O-])=O.[K+].[K+]>>ClCCCOC1=CC=C(C=C1)C(C)=O | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:13][cH:14]1.Br[CH2:9][CH2:10][CH2:11][Cl:12]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][Cl:12])[cH:13][cH:14]1 | CC(=O)c1ccc(O)cc1.ClCCCBr | CC(=O)c1ccc(OCCCCl)cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A mixture of p-hydroxyacetophenone (15 g) and 1-bromo-3-chloropropane (12 mL) in acetone (200 mL) was treated with potassium carbonate (17 g). The mixture was stirred at reflux temperature for 18 hours. The reaction was cooled to ambient temperature and filtered. The filtrate was concentrated in vacuo. The residue was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CC(=O)C | null | null | CC(=O)c1ccc(O)cc1.ClCCCBr>CC(=O)C>CC(=O)c1ccc(OCCCCl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eccea7879e364388a1e2ea38cb936705 | C1CCNCC1.Cc1ccn2cc(-c3ccc(OCCCCl)cc3)nc2c1>>Cc1ccn2cc(-c3ccc(OCCCN4CCCCC4)cc3)nc2c1 | ClCCCOC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1.N1CCCCC1>>N1(CCCCC1)CCCOC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1 | [NH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1.Cl[CH2:15][CH2:14][CH2:13][O:12][c:11]1[cH:10][cH:9][c:8](-[c:7]2[cH:6][n:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:26][c:25]3[n:24]2)[cH:23][cH:22]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]4[CH2:17][CH2:18][CH2:... | C1CCNCC1.Cc1ccn2cc(-c3ccc(OCCCCl)cc3)nc2c1 | Cc1ccn2cc(-c3ccc(OCCCN4CCCCC4)cc3)nc2c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccn2cc(-c3ccc(OCCCN4CCCCC4)cc3)nc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | The product of Step C (0.2 g) and piperidine (2.0 mL) were heated at reflux temperature for 5 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL). The aqueous portion was extracted with additional ethyl acetate (10 mL) and... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccn2ccnc2c1.c1ccccc1.C1CC[NH]CC1 | HCl | null | null | null | C1CCNCC1.Cc1ccn2cc(-c3ccc(OCCCCl)cc3)nc2c1>>Cc1ccn2cc(-c3ccc(OCCCN4CCCCC4)cc3)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4e59850cfc72451ebafb7bb369e48245 | BrBr.CC(=O)c1ccc(O)cc1>>O=C(CBr)c1ccc(O)cc1 | BrBr.CC(=O)C=1C=CC(=CC1)O.C([O-])(O)=O.[Na+]>>C1=CC(=CC=C1C(=O)CBr)O | Br[Br:4].[O:1]=[C:2]([CH3:3])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1>>[O:1]=[C:2]([CH2:3][Br:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1 | BrBr.CC(=O)c1ccc(O)cc1 | O=C(CBr)c1ccc(O)cc1 | null | null | CCOCC | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | 59.6 | [{"value": 59.6, "product": "C1=CC(=CC=C1C(=O)CBr)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Bromine (17.6 g, 110 mmol) was added dropwise to a 0° C. solution of 4-hydroxyacetophenone (15 g, 110 mmol) in ether (200 mL) over 20 minutes. The mixture was stirred for 1 hour. and poured carefully into saturated sodium bicarbonate solution (500 mL). The organics were washed with saturated sodium bicarbonate solution... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | CCOCC | null | 1 | BrBr.CC(=O)c1ccc(O)cc1>CCOCC>O=C(CBr)c1ccc(O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-89b3812d310740d09bd5715b636640df | CC(=O)c1cccc(O)c1.ClCCCBr>>CC(=O)c1cccc(OCCCCl)c1 | OC=1C=C(C=CC1)C(C)=O.BrCCCCl.C([O-])([O-])=O.[K+].[K+]>>ClCCCOC=1C=C(C=CC1)C(C)=O | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[cH:14]1.Br[CH2:10][CH2:11][CH2:12][Cl:13]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][Cl:13])[cH:14]1 | CC(=O)c1cccc(O)c1.ClCCCBr | CC(=O)c1cccc(OCCCCl)c1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A mixture of 3′-hydroxyacetophenone (5 g) and 1-bromo-3-chloropropane (5.0 mL) in acetone (40 mL) was treated with potassium carbonate (8.1 g). The mixture was stirred at reflux temperature for 17 hours. The reaction was cooled to ambient temperature and filtered. The filtrate was concentrated in vacuo. The residue was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CC(=O)C | null | null | CC(=O)c1cccc(O)c1.ClCCCBr>CC(=O)C>CC(=O)c1cccc(OCCCCl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc9dcb2a36e24c068b009367510622ad | BrBr.CC(=O)c1cccc(OCCCCl)c1>>O=C(CBr)c1cccc(OCCCCl)c1 | C([O-])(O)=O.[Na+].ClCCCOC=1C=C(C=CC1)C(C)=O.BrBr>>BrCC(=O)C1=CC(=CC=C1)OCCCCl | Br[Br:4].[O:1]=[C:2]([CH3:3])[c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][CH2:13][Cl:14])[cH:15]1>>[O:1]=[C:2]([CH2:3][Br:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][CH2:13][Cl:14])[cH:15]1 | BrBr.CC(=O)c1cccc(OCCCCl)c1 | O=C(CBr)c1cccc(OCCCCl)c1 | null | null | CCOCC | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | 26 | HOUR | A solution of the product of Step A (2.1 g) in ether (11 mL) was treated with bromine (0.53 mL) and the mixture stirred for 26 hours. The mixture was poured into saturated sodium bicarbonate solution (50 mL) and the organic layer was separated. The aqueous layer was washed with a fresh portion of ether (50 mL) and the ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | CCOCC | null | 26 | BrBr.CC(=O)c1cccc(OCCCCl)c1>CCOCC>O=C(CBr)c1cccc(OCCCCl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-47a419c279bd4298997bf49bc82a7f5a | Cc1ccnc(N)c1.O=C(CBr)c1cccc(OCCCCl)c1>>Cc1ccn2cc(-c3cccc(OCCCCl)c3)nc2c1 | BrCC(=O)C1=CC(=CC=C1)OCCCCl.NC1=NC=CC(=C1)C>>ClCCCOC=1C=C(C=CC1)C=1N=C2N(C=CC(=C2)C)C1 | [CH3:1][c:2]1[cH:3][cH:4][n:5][c:20]([NH2:19])[cH:21]1.O=[C:7]([CH2:6]Br)[c:8]1[cH:9][cH:10][cH:11][c:12]([O:13][CH2:14][CH2:15][CH2:16][Cl:17])[cH:18]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][c:12]([O:13][CH2:14][CH2:15][CH2:16][Cl:17])[cH:18]3)[n:19][c:20]2[cH:21]1 | Cc1ccnc(N)c1.O=C(CBr)c1cccc(OCCCCl)c1 | Cc1ccn2cc(-c3cccc(OCCCCl)c3)nc2c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 98b9b4632b0457bc035e4a4d36e0a1658474c53cb0def2f4c4d097bbd0d48009 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc(-c2cn3ccccc3n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[n;H0;D2;+0:11]:[c:12]:[c:13]>>[c:7]:[c:6]:[c;H0;D3;+0:3](-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:11](:[c:12]:[c:13]):[c:9](:[c:10]):[n;H0;D2;+0:8]:1):[c:4]:[c:5] | 48.7 | [{"value": 48.7, "product": "ClCCCOC=1C=C(C=CC1)C=1N=C2N(C=CC(=C2)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the product of Step B (2.6 g) and 2-amino-4-picoline (0.96 g) in ethanol (10 mL) was heated at 73° C. for 2 hours. The reaction mixture was cooled to ambient temperature and the solvent evaporated in vacuo. The residue was dissolved in dichloromethane (75 mL), washed with saturated sodium bicarbonate solu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1.c1ccccc1 | HBr | C(C)O | null | null | Cc1ccnc(N)c1.O=C(CBr)c1cccc(OCCCCl)c1>C(C)O>Cc1ccn2cc(-c3cccc(OCCCCl)c3)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eaa02a8614da45c299af3040166d233e | C1CCNCC1.Cc1ccn2cc(-c3cccc(OCCCCl)c3)nc2c1>>Cc1ccn2cc(-c3cccc(OCCCN4CCCCC4)c3)nc2c1 | ClCCCOC=1C=C(C=CC1)C=1N=C2N(C=CC(=C2)C)C1.N1CCCCC1>>CC1=CC=2N(C=C1)C=C(N2)C2=CC(=CC=C2)OCCCN2CCCCC2 | [NH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1.Cl[CH2:16][CH2:15][CH2:14][O:13][c:12]1[cH:11][cH:10][cH:9][c:8](-[c:7]2[cH:6][n:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:26][c:25]3[n:24]2)[cH:23]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][cH:11][c:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]4[CH2:18][CH2:1... | C1CCNCC1.Cc1ccn2cc(-c3cccc(OCCCCl)c3)nc2c1 | Cc1ccn2cc(-c3cccc(OCCCN4CCCCC4)c3)nc2c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(OCCCN2CCCCC2)cc(-c2cn3ccccc3n2)c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | The product of Step C (271 mg) and piperidine (2.0 mL) were heated at 100° C. for 2 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL). The aqueous portion was extracted with a fresh portion of ethyl acetate (10 mL) and t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccn2ccnc2c1.c1ccccc1.C1CC[NH]CC1 | HCl | null | null | null | C1CCNCC1.Cc1ccn2cc(-c3cccc(OCCCCl)c3)nc2c1>>Cc1ccn2cc(-c3cccc(OCCCN4CCCCC4)c3)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-838c0cefe9b94edaae563cc0b0c31601 | ClCCCOc1ccc(-c2cn3ccccc3n2)cc1>>ClCCCOc1ccc(-c2cn3c(n2)CCCC3)cc1 | ClCCCOC1=CC=C(C=C1)C=1N=C2N(C=CC=C2)C1>>ClCCCOC1=CC=C(C=C1)C=1N=C2N(CCCC2)C1 | [Cl:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][n:12]3[c:13]([n:14]2)[cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20]1>>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][n:12]3[c:13]([n:14]2)[CH2:15][CH2:16][CH2:17][CH2:18]3)[cH:19][cH:20]1 | ClCCCOc1ccc(-c2cn3ccccc3n2)cc1 | ClCCCOc1ccc(-c2cn3c(n2)CCCC3)cc1 | null | [Pt](=O)=O | CO.C(C)O | Reduction | OtherReaction | 54bbe655e60ef26e7fb7e8075f0419068ea27c3108f7326bbc2999af51513576 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(-c2cn3c(n2)CCCC3)cc1 | [#7;a:1]1:[c:2]:[c:3]:[#7;a:4]2:[cH;D2;+0:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[c:9]:1:2>>[#7;a:1]1:[c:2]:[c:3]:[#7;a:4]2:[c:9]:1-[CH2;D2;+0:8]-[CH2;D2;+0:7]-[CH2;D2;+0:6]-[CH2;D2;+0:5]-2 | 96.4 | [{"value": 96.4, "product": "ClCCCOC1=CC=C(C=C1)C=1N=C2N(CCCC2)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a Parr bottle charged with a mixture of platinum (IV) oxide (30 mg) in ethanol (3 mL) was added a solution of the product of Step A (90 mg) in methanol (6 ml). The mixture was hydrogenated at 40 psi for 4 hours and filtered through a Celite pad which was rinsed with several additional milliliters of methanol and eth... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccn2ccnc2c1 | c1cn2c(n1)CCCC2 | c1ccccc1.c1cn2c(n1)CCCC2 | null | [Pt](=O)=O.CO.C(C)O | null | 4 | ClCCCOc1ccc(-c2cn3ccccc3n2)cc1>[Pt](=O)=O.CO.C(C)O>ClCCCOc1ccc(-c2cn3c(n2)CCCC3)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5cc812fae5524069a85a9f6a363f1a03 | C1CCNCC1.ClCCCOc1ccc(-c2cn3c(n2)CCCC3)cc1>>c1cc(-c2cn3c(n2)CCCC3)ccc1OCCCN1CCCCC1 | ClCCCOC1=CC=C(C=C1)C=1N=C2N(CCCC2)C1.N1CCCCC1>>N1(CCCCC1)CCCOC1=CC=C(C=C1)C=1N=C2N(CCCC2)C1 | [NH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1.Cl[CH2:19][CH2:18][CH2:17][O:16][c:15]1[cH:1][cH:2][c:3](-[c:4]2[cH:5][n:6]3[c:7]([n:8]2)[CH2:9][CH2:10][CH2:11][CH2:12]3)[cH:13][cH:14]1>>[cH:1]1[cH:2][c:3](-[c:4]2[cH:5][n:6]3[c:7]([n:8]2)[CH2:9][CH2:10][CH2:11][CH2:12]3)[cH:13][cH:14][c:15]1[O:16][CH2:17][CH2:18][CH2... | C1CCNCC1.ClCCCOc1ccc(-c2cn3c(n2)CCCC3)cc1 | c1cc(-c2cn3c(n2)CCCC3)ccc1OCCCN1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(-c2cn3c(n2)CCCC3)ccc1OCCCN1CCCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | The product of Step B (83 mg) and piperidine (1.0 mL) were heated at 100° C. for 1.5 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL). The aqueous portion was extracted with a fresh portion of ethyl acetate (2×10 mL) an... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1cn2c(n1)CCCC2.C1CC[NH]CC1 | HCl | null | null | null | C1CCNCC1.ClCCCOc1ccc(-c2cn3c(n2)CCCC3)cc1>>c1cc(-c2cn3c(n2)CCCC3)ccc1OCCCN1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-375e67c322b3421da715227098661d7f | C1CCNCC1.Cc1cc(OCCCCl)ccc1-c1cn2c(n1)CC(C)CC2>>Cc1cc(OCCCN2CCCCC2)ccc1-c1cn2c(n1)CC(C)CC2 | ClCCCOC1=CC(=C(C=C1)C=1N=C2N(CCC(C2)C)C1)C.N1CCCCC1>>CC1CC=2N(CC1)C=C(N2)C2=C(C=C(C=C2)OCCCN2CCCCC2)C | [NH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1.Cl[CH2:8][CH2:7][CH2:6][O:5][c:4]1[cH:3][c:2]([CH3:1])[c:17](-[c:18]2[cH:19][n:20]3[c:21]([n:22]2)[CH2:23][CH:24]([CH3:25])[CH2:26][CH2:27]3)[cH:16][cH:15]1>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][CH2:8][N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][cH:16]... | C1CCNCC1.Cc1cc(OCCCCl)ccc1-c1cn2c(n1)CC(C)CC2 | Cc1cc(OCCCN2CCCCC2)ccc1-c1cn2c(n1)CC(C)CC2 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(-c2cn3c(n2)CCCC3)ccc1OCCCN1CCCCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7]-[C:8] | null | [] | null | null | null | null | The product of Step A (49 mg) and piperidine (1.0 mL) were heated at 100° C. for 2 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL). The aqueous portion was extracted with a fresh portion of ethyl acetate (2×10 mL) and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1cn2c(n1)CCCC2 | HCl | null | null | null | C1CCNCC1.Cc1cc(OCCCCl)ccc1-c1cn2c(n1)CC(C)CC2>>Cc1cc(OCCCN2CCCCC2)ccc1-c1cn2c(n1)CC(C)CC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-15da65bf675c4180b4c07eda81b5323b | BrBr.CC(=O)c1ccc(OCCCCl)cc1F>>O=C(CBr)c1ccc(OCCCCl)cc1F | C([O-])(O)=O.[Na+].FC1=C(C=CC(=C1)OCCCCl)C(C)=O.BrBr>>BrCC(=O)C1=C(C=C(C=C1)OCCCCl)F | Br[Br:4].[O:1]=[C:2]([CH3:3])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][Cl:13])[cH:14][c:15]1[F:16]>>[O:1]=[C:2]([CH2:3][Br:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][CH2:12][Cl:13])[cH:14][c:15]1[F:16] | BrBr.CC(=O)c1ccc(OCCCCl)cc1F | O=C(CBr)c1ccc(OCCCCl)cc1F | null | null | CCOCC | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | 17 | HOUR | A solution of the product of Step A (2.3 g) in ether (10 mL) was treated with bromine (0.51 mL) and the mixture stirred for approximately 17 hours. The mixture was slowly poured into saturated sodium bicarbonate solution (40 mL) and then the organic layer was separated. The aqueous layer was washed with a fresh portion... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | CCOCC | null | 17 | BrBr.CC(=O)c1ccc(OCCCCl)cc1F>CCOCC>O=C(CBr)c1ccc(OCCCCl)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-95e42f03238643bf8dd17789479a8a05 | Cc1ccnc(N)c1.O=C(CBr)c1ccc(OCCCCl)cc1F>>Cc1ccn2cc(-c3ccc(OCCCCl)cc3F)nc2c1 | BrCC(=O)C1=C(C=C(C=C1)OCCCCl)F.NC1=NC=CC(=C1)C>>ClCCCOC1=CC(=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1)F | [CH3:1][c:2]1[cH:3][cH:4][n:5][c:21]([NH2:20])[cH:22]1.O=[C:7]([CH2:6]Br)[c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])[cH:17][c:18]1[F:19]>>[CH3:1][c:2]1[cH:3][cH:4][n:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])[cH:17][c:18]3[F:19])[n:20][c:21]2[cH:22]1 | Cc1ccnc(N)c1.O=C(CBr)c1ccc(OCCCCl)cc1F | Cc1ccn2cc(-c3ccc(OCCCCl)cc3F)nc2c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 98b9b4632b0457bc035e4a4d36e0a1658474c53cb0def2f4c4d097bbd0d48009 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc(-c2cn3ccccc3n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6](-[F;D1;H0:7]):[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[n;H0;D2;+0:12]:[c:13]:[c:14]>>[F;D1;H0:7]-[c:6](:[c:8]):[c;H0;D3;+0:3](-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:12](:[c:13]:[c:14]):[c:10](:[c:11]):[n;H0;D2;+0:9]:1):[c:4]:[c:5] | null | [] | null | null | null | null | A solution of the product of Step B (1.0 g) and 2-amino-4-picoline (0.357 g) in ethanol (4 mL) was heated at 73° C. for 18 hours. The reaction mixture was cooled to ambient temperature and the solvent evaporated in vacuo. A portion of the residue was purified via silica gel chromatography (ethyl acetate/hexane) directl... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1.c1ccccc1 | HBr | C(C)O | null | null | Cc1ccnc(N)c1.O=C(CBr)c1ccc(OCCCCl)cc1F>C(C)O>Cc1ccn2cc(-c3ccc(OCCCCl)cc3F)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-38df20f512e84f7faadc91d1b13aecdb | C1CCNCC1.Cc1ccn2cc(-c3ccc(OCCCCl)cc3F)nc2c1>>Cc1ccn2cc(-c3ccc(OCCCN4CCCCC4)cc3F)nc2c1 | ClCCCOC1=CC(=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1)F.N1CCCCC1>>N1(CCCCC1)CCCOC1=CC(=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1)F | [NH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1.Cl[CH2:15][CH2:14][CH2:13][O:12][c:11]1[cH:10][cH:9][c:8](-[c:7]2[cH:6][n:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:27][c:26]3[n:25]2)[c:23]([F:24])[cH:22]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]4[CH2:17][CH2:1... | C1CCNCC1.Cc1ccn2cc(-c3ccc(OCCCCl)cc3F)nc2c1 | Cc1ccn2cc(-c3ccc(OCCCN4CCCCC4)cc3F)nc2c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccn2cc(-c3ccc(OCCCN4CCCCC4)cc3)nc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | The product of Step C (118 mg) and piperidine (1.5 mL) were heated at 100° C. for 2.5 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL). The aqueous portion was extracted with additional ethyl acetate (10 mL) and the org... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccn2ccnc2c1.c1ccccc1.C1CC[NH]CC1 | HCl | null | null | null | C1CCNCC1.Cc1ccn2cc(-c3ccc(OCCCCl)cc3F)nc2c1>>Cc1ccn2cc(-c3ccc(OCCCN4CCCCC4)cc3F)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d09efd5bbd8744ae90df923aa5ef3ad5 | CC(=O)c1ccc(O)cc1C.ClCCCBr>>CC(=O)c1ccc(OCCCCl)cc1C | OC1=CC(=C(C=C1)C(C)=O)C.BrCCCCl.C([O-])([O-])=O.[K+].[K+]>>CC1=C(C=CC(=C1)OCCCCl)C(C)=O | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:13][c:14]1[CH3:15].Br[CH2:9][CH2:10][CH2:11][Cl:12]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][Cl:12])[cH:13][c:14]1[CH3:15] | CC(=O)c1ccc(O)cc1C.ClCCCBr | CC(=O)c1ccc(OCCCCl)cc1C | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 50 | CELSIUS | 18 | HOUR | A mixture of 4′-hydroxy-2′-methyl-acetophenone (10.5 g) and 1-bromo-3-chloropropane (7.6 mL) in acetone (70 mL) was treated with potassium carbonate (14.5 g). The mixture was stirred at 50° C. for approximately 18 hours. The reaction mixture was cooled to ambient temperature and partitioned between dichloromethane (200... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CC(=O)C | 50 | 18 | CC(=O)c1ccc(O)cc1C.ClCCCBr>CC(=O)C>CC(=O)c1ccc(OCCCCl)cc1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4527f79af08042b88d0e1d11f714554a | BrBr.CC(=O)c1ccc(OCCCCl)cc1C>>Cc1cc(OCCCCl)ccc1C(=O)CBr | C([O-])(O)=O.[Na+].CC1=C(C=CC(=C1)OCCCCl)C(C)=O.BrBr>>BrCC(=O)C1=C(C=C(C=C1)OCCCCl)C | Br[Br:16].[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][CH2:8][Cl:9])[cH:10][cH:11][c:12]1[C:13](=[O:14])[CH3:15]>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][CH2:8][Cl:9])[cH:10][cH:11][c:12]1[C:13](=[O:14])[CH2:15][Br:16] | BrBr.CC(=O)c1ccc(OCCCCl)cc1C | Cc1cc(OCCCCl)ccc1C(=O)CBr | null | null | CCOCC | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | 17 | HOUR | A solution of the product of Step A (9.33 g) in ether (42 mL) was treated with bromine (2.1 mL) and the mixture stirred for approximately 17 hours. The mixture was slowly poured into saturated sodium bicarbonate solution (100 mL) and then the organic layer was separated. The aqueous layer was washed with a fresh portio... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | CCOCC | null | 17 | BrBr.CC(=O)c1ccc(OCCCCl)cc1C>CCOCC>Cc1cc(OCCCCl)ccc1C(=O)CBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9e3c8858286e46a0b9d74b5d94f6f030 | Cc1cc(OCCCCl)ccc1C(=O)CBr.Cc1ccnc(N)c1>>Cc1ccn2cc(-c3ccc(OCCCCl)cc3C)nc2c1 | BrCC(=O)C1=C(C=C(C=C1)OCCCCl)C.NC1=NC=CC(=C1)C>>ClCCCOC1=CC(=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1)C | O=[C:7]([CH2:6]Br)[c:8]1[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])[cH:17][c:18]1[CH3:19].[CH3:1][c:2]1[cH:3][cH:4][n:5][c:21]([NH2:20])[cH:22]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])[cH:17][c:18]3[CH3:19])[n:20][c:21]2[cH:22]1 | Cc1cc(OCCCCl)ccc1C(=O)CBr.Cc1ccnc(N)c1 | Cc1ccn2cc(-c3ccc(OCCCCl)cc3C)nc2c1 | null | null | CO.ClCCl.C(C)O | Aromatic Heterocycle Formation | OtherReaction | 98b9b4632b0457bc035e4a4d36e0a1658474c53cb0def2f4c4d097bbd0d48009 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc(-c2cn3ccccc3n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6](-[C;D1;H3:7]):[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[n;H0;D2;+0:12]:[c:13]:[c:14]>>[C;D1;H3:7]-[c:6](:[c:8]):[c;H0;D3;+0:3](-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:12](:[c:13]:[c:14]):[c:10](:[c:11]):[n;H0;D2;+0:9]:1):[c:4]:[c:5] | null | [] | null | null | null | null | A solution of the product of Step B (6.77 g) and 2-amino-4-picoline (2.4 g) in ethanol (22 mL) was heated at 72° C. for 10 hours. The reaction mixture was cooled to ambient temperature and dissolved in methanol/dichloromethane and treated with Dowex® 550A basic resin until the pH of the mixture was 7. The resin was rem... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1.c1ccccc1 | HBr | CO.ClCCl.C(C)O | null | null | Cc1cc(OCCCCl)ccc1C(=O)CBr.Cc1ccnc(N)c1>CO.ClCCl.C(C)O>Cc1ccn2cc(-c3ccc(OCCCCl)cc3C)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-10566c0e50794107a81bcc44b7c8cf04 | C1CCNCC1.Cc1ccn2cc(-c3ccc(OCCCCl)cc3C)nc2c1>>Cc1ccn2cc(-c3ccc(OCCCN4CCCCC4)cc3C)nc2c1 | ClCCCOC1=CC(=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1)C.N1CCCCC1>>N1(CCCCC1)CCCOC1=CC(=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1)C | [NH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1.Cl[CH2:15][CH2:14][CH2:13][O:12][c:11]1[cH:10][cH:9][c:8](-[c:7]2[cH:6][n:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:27][c:26]3[n:25]2)[c:23]([CH3:24])[cH:22]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]4[CH2:17][CH2... | C1CCNCC1.Cc1ccn2cc(-c3ccc(OCCCCl)cc3C)nc2c1 | Cc1ccn2cc(-c3ccc(OCCCN4CCCCC4)cc3C)nc2c1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccn2cc(-c3ccc(OCCCN4CCCCC4)cc3)nc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | The product of Step C (200 mg) and piperidine (2.0 mL) were heated at 100° C. for 2.5 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL). The aqueous portion was extracted with additional ethyl acetate (10 mL) and the org... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccn2ccnc2c1.c1ccccc1.C1CC[NH]CC1 | HCl | null | null | null | C1CCNCC1.Cc1ccn2cc(-c3ccc(OCCCCl)cc3C)nc2c1>>Cc1ccn2cc(-c3ccc(OCCCN4CCCCC4)cc3C)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-979a976b36f74db790007f7dd4f936ca | COc1cc(C(=O)CBr)ccc1OCCCCl.Cc1ccnc(N)c1>>Br.COc1cc(-c2cn3ccc(C)cc3n2)ccc1OCCCCl | BrCC(=O)C1=CC(=C(C=C1)OCCCCl)OC.NC1=NC=CC(=C1)C>>Br.ClCCCOC1=C(C=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1)OC | O=[C:7]([c:6]1[cH:5][c:4]([O:3][CH3:2])[c:19]([O:20][CH2:21][CH2:22][CH2:23][Cl:24])[cH:18][cH:17]1)[CH2:8][Br:1].[n:9]1[cH:10][cH:11][c:12]([CH3:13])[cH:14][c:15]1[NH2:16]>>[BrH:1].[CH3:2][O:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][n:9]3[cH:10][cH:11][c:12]([CH3:13])[cH:14][c:15]3[n:16]2)[cH:17][cH:18][c:19]1[O:20][CH2:21][C... | COc1cc(C(=O)CBr)ccc1OCCCCl.Cc1ccnc(N)c1 | Br.COc1cc(-c2cn3ccc(C)cc3n2)ccc1OCCCCl | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 98b9b4632b0457bc035e4a4d36e0a1658474c53cb0def2f4c4d097bbd0d48009 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc(-c2cn3ccccc3n2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[Br;H0;D1;+0:3])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[n;H0;D2;+0:12]:[c:13]:[c:14]>>[BrH;D0;+0:3].[c:14]:[c:13]:[n;H0;D3;+0:12]1:[cH;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[n;H0;D2;+0:9]:[c:10]:1:[c:11] | 70.5 | [{"value": 70.5, "product": "Br.ClCCCOC1=C(C=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | A solution of the product of Step B (1.44 g) and 2-amino-4-picoline (0.486 g) in ethanol (6 mL) was heated at 73° C. for 1 hour. The reaction mixture was cooled to ambient temperature and evaporated to a yellow solid. The solid was stirred with 25 mL of dichloromethane for approximately 10 minutes. The mixture was filt... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | HO- | C(C)O | null | 0.166667 | COc1cc(C(=O)CBr)ccc1OCCCCl.Cc1ccnc(N)c1>C(C)O>Br.COc1cc(-c2cn3ccc(C)cc3n2)ccc1OCCCCl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-66426ac545ed4e13990d7efe19725d70 | C1CCNCC1.COc1cc(-c2cn3ccc(C)cc3n2)ccc1OCCCCl>>COc1cc(-c2cn3ccc(C)cc3n2)ccc1OCCCN1CCCCC1 | Br.ClCCCOC1=C(C=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1)OC.N1CCCCC1>>N1(CCCCC1)CCCOC1=C(C=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1)OC | [NH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1.Cl[CH2:22][CH2:21][CH2:20][O:19][c:18]1[c:3]([O:2][CH3:1])[cH:4][c:5](-[c:6]2[cH:7][n:8]3[cH:9][cH:10][c:11]([CH3:12])[cH:13][c:14]3[n:15]2)[cH:16][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][n:8]3[cH:9][cH:10][c:11]([CH3:12])[cH:13][c:14]3[n:15]2)[cH:16][cH:17... | C1CCNCC1.COc1cc(-c2cn3ccc(C)cc3n2)ccc1OCCCCl | COc1cc(-c2cn3ccc(C)cc3n2)ccc1OCCCN1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccn2cc(-c3ccc(OCCCN4CCCCC4)cc3)nc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | The product of Step C (184 mg) and piperidine (1.5 mL) were heated at 100° C. for 4 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL). The aqueous portion was extracted twice with additional ethyl acetate (10 mL) and onc... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccn2ccnc2c1.C1CC[NH]CC1 | HCl | null | null | null | C1CCNCC1.COc1cc(-c2cn3ccc(C)cc3n2)ccc1OCCCCl>>COc1cc(-c2cn3ccc(C)cc3n2)ccc1OCCCN1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-062f5d4b3c2849adbc8b1554248e2c83 | Cc1cccn2cc(-c3ccc([N+](=O)[O-])cc3)nc12>>Cc1cccn2cc(-c3ccc(N)cc3)nc12 | [N+](=O)([O-])C1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1.C1=CCC=CC1>>NC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1 | O=[N+:13]([O-])[c:12]1[cH:11][cH:10][c:9](-[c:8]2[cH:7][n:6]3[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:17]3[n:16]2)[cH:15][cH:14]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([NH2:13])[cH:14][cH:15]3)[n:16][c:17]12 | Cc1cccn2cc(-c3ccc([N+](=O)[O-])cc3)nc12 | Cc1cccn2cc(-c3ccc(N)cc3)nc12 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(-c2cn3ccccc3n2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 54.4 | [{"value": 54.4, "product": "NC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of the product of Step A (1.48 g) and 1,4-cyclohexadiene (6.2 mL) and palladium (10% wt on activated carbon) (1.4 g) in ethanol (100 mL) was stirred at reflux temperature for 2 hours and cooled to ambient temperature and stirred for 12 hours. The reaction mixture was filtered through a pad of celite and the c... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccn2ccnc2c1.c1ccccc1 | Other | [Pd].C(C)O | null | null | Cc1cccn2cc(-c3ccc([N+](=O)[O-])cc3)nc12>[Pd].C(C)O>Cc1cccn2cc(-c3ccc(N)cc3)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e9297e9f797943d9b05989f796ddd673 | Cc1cccn2cc(-c3ccc(N)cc3)nc12.O=C(O)CCN1CCCCC1>>Cc1cccn2cc(-c3ccc(NC(=O)CCN4CCCCC4)cc3)nc12 | N1(CCCCC1)CCC(=O)O.CCN=C=NCCCN(C)C.Cl.O.ON1N=NC2=C1C=CC=C2.NC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1.C(C)(C)N(C(C)C)CC>>N1(CCCCC1)CCC(=O)NC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([NH2:13])[cH:24][cH:25]3)[n:26][c:27]12.O[C:14](=[O:15])[CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([NH:13][C:14](=[O:15])[CH2:16][CH2:17][N:18]... | Cc1cccn2cc(-c3ccc(N)cc3)nc12.O=C(O)CCN1CCCCC1 | Cc1cccn2cc(-c3ccc(NC(=O)CCN4CCCCC4)cc3)nc12 | null | null | ClCCl.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCN1CCCCC1)Nc1ccc(-c2cn3ccccc3n2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 23.9 | [{"value": 23.9, "product": "N1(CCCCC1)CCC(=O)NC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a mixture of the product of Step B (330 mg) and N,N-diisopropylethylamine (0.28 mL) in dichloromethane (3 mL) and N,N-dimethylformamide (1 mL), was added 1-piperidinepropionic acid (256 mg), WSC.HCl (1-Ethyl-3-(3′dimethylaminopropyl)-carbodiimide.HCl) (312 mg), and 1-hydroxybenzotriazole hydrate (220 mg). The soluti... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccn2ccnc2c1.c1ccccc1.C1CC[NH]CC1 | HO- | ClCCl.CN(C=O)C | null | 18 | Cc1cccn2cc(-c3ccc(N)cc3)nc12.O=C(O)CCN1CCCCC1>ClCCl.CN(C=O)C>Cc1cccn2cc(-c3ccc(NC(=O)CCN4CCCCC4)cc3)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e96def60df7d43e5a370fd4e9b82ffa2 | Cc1cccn2cc(-c3ccc(NC(=O)CCN4CCCCC4)cc3)nc12>>Cc1cccn2cc(-c3ccc(NCCCN4CCCC4)cc3)nc12 | N1(CCCCC1)CCC(=O)NC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1>>N1(CCCC1)CCCNC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1 | O=[C:14]([NH:13][c:12]1[cH:11][cH:10][c:9](-[c:8]2[cH:7][n:6]3[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:25]3[n:24]2)[cH:23][cH:22]1)[CH2:15][CH2:16][N:17]1[CH2:18]C[CH2:19][CH2:20][CH2:21]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([NH:13][CH2:14][CH2:15][CH2:16][N:17]4[CH2:18][CH2:19][CH2:... | Cc1cccn2cc(-c3ccc(NC(=O)CCN4CCCCC4)cc3)nc12 | Cc1cccn2cc(-c3ccc(NCCCN4CCCC4)cc3)nc12 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 9c51f2ab4e8ed51c3fc6887357cca51449a8c34c42454c289e25fb78eb6c5b1b | a267a1d067671b1e552868d2a160d189ea3d111697964c07c12357f5fdb70c13 | c1ccn2cc(-c3ccc(NCCCN4CCCC4)cc3)nc2c1 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[C:4]-[C:5]-[#7:6]1-[C:7]-[C:8]-[CH2;D2;+0:9]-C-[CH2;D2;+0:10]-1>>[c:3]-[#7:2]-[CH2;D2;+0:1]-[C:4]-[C:5]-[#7:6]1-[C:7]-[C:8]-[CH2;D2;+0:9]-[CH2;D2;+0:10]-1 | 53.3 | [{"value": 53.3, "product": "N1(CCCC1)CCCNC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of the product of Step C (122 mg) and borane-methylsulfide complex (0.5 mL of a 2M solution in toluene) in toluene (3.5 mL) was stirred and heated at reflux for 18 hours. The mixture was cooled to ambient temperature and evaporated. The residue was treated with 1M HCl (10 mL) and heated to reflux. The aqueous... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | C1CC[NH]CC1 | C1CC[NH]C1 | c1ccn2ccnc2c1.c1ccccc1.C1CC[NH]C1 | Other | C1(=CC=CC=C1)C | null | null | Cc1cccn2cc(-c3ccc(NC(=O)CCN4CCCCC4)cc3)nc12>C1(=CC=CC=C1)C>Cc1cccn2cc(-c3ccc(NCCCN4CCCC4)cc3)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e6db157d18cf461c8d370ac086ebe049 | Cc1ccnc(N)c1.O=C(CBr)c1ccc(Br)cc1>>Cc1ccn2cc(-c3ccc(Br)cc3)nc2c1 | BrCC(=O)C1=CC=C(C=C1)Br.NC1=NC=CC(=C1)C>>BrC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1 | [CH3:1][c:2]1[cH:3][cH:4][n:5][c:16]([NH2:15])[cH:17]1.O=[C:7]([CH2:6]Br)[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]3)[n:15][c:16]2[cH:17]1 | Cc1ccnc(N)c1.O=C(CBr)c1ccc(Br)cc1 | Cc1ccn2cc(-c3ccc(Br)cc3)nc2c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 98b9b4632b0457bc035e4a4d36e0a1658474c53cb0def2f4c4d097bbd0d48009 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc(-c2cn3ccccc3n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[n;H0;D2;+0:11]:[c:12]:[c:13]>>[c:7]:[c:6]:[c;H0;D3;+0:3](-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:11](:[c:12]:[c:13]):[c:9](:[c:10]):[n;H0;D2;+0:8]:1):[c:4]:[c:5] | 56.8 | [{"value": 56.8, "product": "BrC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2,4′-dibromoacetophenone (22.4 g) and 2-amino-4-picoline (8.68 g) in ethanol (80 mL) was heated at reflux temperature for 3 hours. The reaction mixture was cooled to ambient temperature and the crystalline solid isolated by filtration, washed with ethanol and dried in vacuo to give the title compound (13.1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1.c1ccccc1 | HBr | C(C)O | null | null | Cc1ccnc(N)c1.O=C(CBr)c1ccc(Br)cc1>C(C)O>Cc1ccn2cc(-c3ccc(Br)cc3)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-68e35b96105c48e0ba0ea364160d7487 | C#CCCO.Cc1ccn2cc(-c3ccc(Br)cc3)nc2c1>>Cc1ccn2cc(-c3ccc(C#CCCO)cc3)nc2c1 | BrC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1.C(C)N(CC)CC.C(CC#C)O>>OCCC#CC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1 | [CH:12]#[C:13][CH2:14][CH2:15][OH:16].Br[c:11]1[cH:10][cH:9][c:8](-[c:7]2[cH:6][n:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:21][c:20]3[n:19]2)[cH:18][cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([C:12]#[C:13][CH2:14][CH2:15][OH:16])[cH:17][cH:18]3)[n:19][c:20]2[cH:21]1 | C#CCCO.Cc1ccn2cc(-c3ccc(Br)cc3)nc2c1 | Cc1ccn2cc(-c3ccc(C#CCCO)cc3)nc2c1 | 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.[Cu]I | C(C)#N | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc(-c2cn3ccccc3n2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[C:7]#[CH;D1;+0:8]>>[C:6]-[C:7]#[C;H0;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 71.7 | [{"value": 71.7, "product": "OCCC#CC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | The product of Step A (1.8 g) in dry acetonitrile (40 mL) was treated sequentially with tetrakis(triphenylphosphine)palladium(0) (0.1 g), triethylamine (1.27 g), and CuI (10 mg) then heated at 60° C. for 30 minutes. The mixture was cooled to ambient temperature, treated with 3-butyn-1-ol (0.361 g) and heated at reflux ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccn2ccnc2c1.c1ccccc1 | HBr | 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.[Cu]I.C(C)#N | 60 | null | C#CCCO.Cc1ccn2cc(-c3ccc(Br)cc3)nc2c1>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.[Cu]I.C(C)#N>Cc1ccn2cc(-c3ccc(C#CCCO)cc3)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c6120ca092854261beae89e60ccc5398 | CS(=O)(=O)Cl.Cc1ccn2cc(-c3ccc(C#CCCO)cc3)nc2c1>>Cc1ccn2cc(-c3ccc(C#CCCOS(C)(=O)=O)cc3)nc2c1 | CS(=O)(=O)Cl.OCCC#CC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1.N1=CC=CC=C1>>CS(=O)(=O)OCCC#CC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1 | Cl[S:17]([CH3:18])(=[O:19])=[O:20].[CH3:1][c:2]1[cH:3][cH:4][n:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([C:12]#[C:13][CH2:14][CH2:15][OH:16])[cH:21][cH:22]3)[n:23][c:24]2[cH:25]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([C:12]#[C:13][CH2:14][CH2:15][O:16][S:17]([CH3:18])(=[O:19])=[O:20])[... | CS(=O)(=O)Cl.Cc1ccn2cc(-c3ccc(C#CCCO)cc3)nc2c1 | Cc1ccn2cc(-c3ccc(C#CCCOS(C)(=O)=O)cc3)nc2c1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(-c2cn3ccccc3n2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]#[C:6]-[C:7]-[C:8]-[OH;D1;+0:9]>>[C:5]#[C:6]-[C:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 66.4 | [{"value": 66.4, "product": "CS(=O)(=O)OCCC#CC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | null | null | The product of Step B (0.135 g) in dichloromethane (3 mL) was treated with pyridine (0.37 g) and cooled to 10° C. The cold solution was treated with methanesulfonyl chloride (0.112 g) and allowed to stir and warm to ambient temperature over 18 hours. The reaction mixture was washed with 1% H2SO4 solution, saturated sod... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccn2ccnc2c1.c1ccccc1 | HCl | ClCCl | 10 | null | CS(=O)(=O)Cl.Cc1ccn2cc(-c3ccc(C#CCCO)cc3)nc2c1>ClCCl>Cc1ccn2cc(-c3ccc(C#CCCOS(C)(=O)=O)cc3)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6414fe018863447e9a234c42b7b4c928 | C1CCNCC1.Cc1ccn2cc(-c3ccc(C#CCCOS(C)(=O)=O)cc3)nc2c1>>Cc1ccn2cc(-c3ccc(C#CCCN4CCCCC4)cc3)nc2c1 | CO.ClCCl.CS(=O)(=O)OCCC#CC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1.N1CCCCC1.C([O-])([O-])=O.[K+].[K+]>>N1(CCCCC1)CCC#CC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1 | [NH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1.CS(=O)(=O)O[CH2:15][CH2:14][C:13]#[C:12][c:11]1[cH:10][cH:9][c:8](-[c:7]2[cH:6][n:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:26][c:25]3[n:24]2)[cH:23][cH:22]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([C:12]#[C:13][CH2:14][CH2:15][N:16]4[CH2:17][CH2:1... | C1CCNCC1.Cc1ccn2cc(-c3ccc(C#CCCOS(C)(=O)=O)cc3)nc2c1 | Cc1ccn2cc(-c3ccc(C#CCCN4CCCCC4)cc3)nc2c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Alkylation of amines | d9333bb5e81b2a4e56015146d2514db60fc0485d8a32b9d10434a86ed081ca83 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | C(#Cc1ccc(-c2cn3ccccc3n2)cc1)CCN1CCCCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3]#[C:4]-[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[C:3]#[C:4]-[c:5])-[C:9]-[C:10] | 103.2 | [{"value": 103.2, "product": "N1(CCCCC1)CCC#CC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The product of Step C (1.00 g) in acetonitrile (15 mL) was treated with piperidine (0.269 g) and potassium carbonate (1.17 g) and heated at reflux for 18 hours. The reaction mixture was cooled to ambient temperature, washed with water (20 mL), dried over magnesium sulfate, filtered and evaporated to give crude product.... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccn2ccnc2c1.c1ccccc1.C1CC[NH]CC1 | MsOH.HO- | C(C)#N | null | null | C1CCNCC1.Cc1ccn2cc(-c3ccc(C#CCCOS(C)(=O)=O)cc3)nc2c1>C(C)#N>Cc1ccn2cc(-c3ccc(C#CCCN4CCCCC4)cc3)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d7ef957ab1cf46f68f1f4c42cdc7ceea | C1CCNCC1.C=CCCBr>>C=CCCN1CCCCC1 | BrCCC=C.N1CCCCC1>>N1(CCCCC1)CCC=C | [NH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1.Br[CH2:4][CH2:3][CH:2]=[CH2:1]>>[CH2:1]=[CH:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1 | C1CCNCC1.C=CCCBr | C=CCCN1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1CCNCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]=[C;D1;H2:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C:2]-[C:3]=[C;D1;H2:4])-[C:8]-[C:9] | 93.4 | [{"value": 93.4, "product": "N1(CCCCC1)CCC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Bromobut-1-ene (1.35 g) was treated with piperidine (1.7 g) and heated at reflux for 3 hours. The mixture was cooled to ambient temperature, filtered and the residue washed with ether (50 mL). The combined filtrate and washings were evaporated to give the title compound (1.3 g).
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HBr | null | null | null | C1CCNCC1.C=CCCBr>>C=CCCN1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c38ca98053b1466699d379c85b5bf9d3 | CS(=O)(=O)Cl.Cc1ccn2cc(-c3ccc(CCCCO)cc3)nc2c1>>Cc1ccn2cc(-c3ccc(CCCCOS(C)(=O)=O)cc3)nc2c1 | CS(=O)(=O)Cl.OCCCCC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1.C(C)N(CC)CC>>CS(=O)(=O)OCCCCC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1 | Cl[S:17]([CH3:18])(=[O:19])=[O:20].[CH3:1][c:2]1[cH:3][cH:4][n:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[cH:21][cH:22]3)[n:23][c:24]2[cH:25]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5]2[cH:6][c:7](-[c:8]3[cH:9][cH:10][c:11]([CH2:12][CH2:13][CH2:14][CH2:15][O:16][S:17]([CH3:18])(=[O:19])=[O... | CS(=O)(=O)Cl.Cc1ccn2cc(-c3ccc(CCCCO)cc3)nc2c1 | Cc1ccn2cc(-c3ccc(CCCCOS(C)(=O)=O)cc3)nc2c1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc(-c2cn3ccccc3n2)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 125.6 | [{"value": 125.6, "product": "CS(=O)(=O)OCCCCC1=CC=C(C=C1)C=1N=C2N(C=CC(=C2)C)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | The product of Step A (0.33 g) in dichloromethane (20 mL) was treated with triethylamine (0.36 g) and cooled to 0° C. The cold solution was treated with methanesulfonyl chloride (0.338 g) and allowed to stir and warm to ambient temperature over 18 hours. The reaction mixture was washed with water (50 mL), saturated sod... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccn2ccnc2c1.c1ccccc1 | HCl | ClCCl | 0 | null | CS(=O)(=O)Cl.Cc1ccn2cc(-c3ccc(CCCCO)cc3)nc2c1>ClCCl>Cc1ccn2cc(-c3ccc(CCCCOS(C)(=O)=O)cc3)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2927bd8c3c9846bbb36c39855a81a50c | C1CCNCC1.C=CCCBr>>C=CCCN1CCCCC1 | BrCCC=C.N1CCCCC1>>N1(CCCCC1)CCC=C | [NH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1.Br[CH2:4][CH2:3][CH:2]=[CH2:1]>>[CH2:1]=[CH:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1 | C1CCNCC1.C=CCCBr | C=CCCN1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | C1CCNCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]=[C;D1;H2:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[C:2]-[C:3]=[C;D1;H2:4])-[C:8]-[C:9] | 93.4 | [{"value": 74.15, "product": "N1(CCCCC1)CCC=C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.4, "product": "N1(CCCCC1)CCC=C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-bromo-3-butene (1.35 g, 10 mmol) and piperidine (1.70 g, 20 mmol) neat was refluxed under nitrogen atmosphere for 3 h. Cooled to RT, filtered and dissolved into ethyl ether (40 mL). Then solution was washed with water (2×30 mL) and dried over anhydrous Na2SO4, filtered and evaporated to dryness to yield ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | HBr | null | null | null | C1CCNCC1.C=CCCBr>>C=CCCN1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c56bedb66ea340c2b3e2c3252be8914e | BrBr.CC(=O)c1ccc(O)cc1>>O=C(CBr)c1ccc(O)cc1 | C([O-])(O)=O.[Na+].C(C)(=O)C1=CC=C(C=C1)O.BrBr>>C1=CC(=CC=C1C(=O)CBr)O | Br[Br:4].[O:1]=[C:2]([CH3:3])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1>>[O:1]=[C:2]([CH2:3][Br:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]1 | BrBr.CC(=O)c1ccc(O)cc1 | O=C(CBr)c1ccc(O)cc1 | null | null | CCOCC | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | 18 | HOUR | 4-Acetylphenol (20 g) in ether (200 mL) was treated with bromine (6.8 mL) and stirred at ambient temperature for 18 hours. The solution was poured into saturated sodium bicarbonate, stirred for 30 minutes and the organic layer separated. The organic portion was washed with saturated sodium bicarbonate, dried over magne... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | CCOCC | null | 18 | BrBr.CC(=O)c1ccc(O)cc1>CCOCC>O=C(CBr)c1ccc(O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b69a26f17c554d17b35eebf5deba32e4 | CC1(N)C=CC=CN1.O=C(CBr)c1ccc(O)cc1>>Cc1cccn2cc(-c3ccc(O)cc3)nc12 | C1=CC(=CC=C1C(=O)CBr)O.NC1(NC=CC=C1)C.C(C)O>>OC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1 | [CH3:1][C:2]1([NH2:16])[NH:6][CH:5]=[CH:4][CH:3]=[CH:17]1.O=[C:8]([CH2:7]Br)[c:9]1[cH:10][cH:11][c:12]([OH:13])[cH:14][cH:15]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([OH:13])[cH:14][cH:15]3)[n:16][c:17]12 | CC1(N)C=CC=CN1.O=C(CBr)c1ccc(O)cc1 | Cc1cccn2cc(-c3ccc(O)cc3)nc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | dcc35b455aa6ded0edfd1880624cde718e291658c25d8b6c50d957d5783886c6 | 8ff56414b472044d7e70d165dc39de3f03608b9f6c1d556e65c90c5fd5b309bc | c1ccc(-c2cn3ccccc3n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[C;D1;H3:8]-[C;H0;D4;+0:9]1(-[NH2;D1;+0:10])-[CH;D2;+0:11]=[CH;D2;+0:12]-[CH;D2;+0:13]=[CH;D2;+0:14]-[NH;D2;+0:15]-1>>[C;D1;H3:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:12]:[cH;D2;+0:13]:[cH;D2;+0:14]:[n;H0;D3;+0:15]2:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c;H0;D3;... | null | [] | null | null | null | null | The product of step A (30 g) and 2-aminopicoline (15 mL) in ethanol (200 mL) was heated at reflux temperature for 4 hours then cooled to ambient temperature. The resulting precipitate containing the title compound was isolated via filtration (27 g).
Conditions: See reaction.notes.procedure_details.
Workup: at reflux te... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Primary halide.Ketone.Primary amine.Conjugated diene | null | C1=CCNC=C1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1.c1ccccc1 | HBr | null | null | null | CC1(N)C=CC=CN1.O=C(CBr)c1ccc(O)cc1>>Cc1cccn2cc(-c3ccc(O)cc3)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-adab4b87712c4dafbdcd55a8abd05d2f | Cc1cccn2cc(-c3ccc(O)cc3)nc12.ClCC1CO1>>Cc1cccn2cc(-c3ccc(OCC4CO4)cc3)nc12 | C(Cl)C1CO1.OC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1.[OH-].[K+]>>O1C(COC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C)C2)C1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([OH:13])[cH:18][cH:19]3)[n:20][c:21]12.Cl[CH2:14][CH:15]1[CH2:16][O:17]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([O:13][CH2:14][CH:15]4[CH2:16][O:17]4)[cH:18][cH:19]3)[n:20][c:21]12 | Cc1cccn2cc(-c3ccc(O)cc3)nc12.ClCC1CO1 | Cc1cccn2cc(-c3ccc(OCC4CO4)cc3)nc12 | null | null | CO.ClCCl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccn2cc(-c3ccc(OCC4CO4)cc3)nc2c1 | Cl-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[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]1-[#8:3]-[C:4]-1):[c:8] | null | [] | null | null | 2 | HOUR | The product of Step B (27 g) in methanol (500 mL) was treated with potassium hydroxide (14 g) and stirred at ambient temperature for 2 hours. To this solution was then added epichlorohydrin (9.4 mL) and the mixture stirred for an additional 48 hours. The reaction mixture was diluted with dichloromethane, filtered and t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccn2ccnc2c1.c1ccccc1.C1CO1 | HCl | CO.ClCCl | null | 2 | Cc1cccn2cc(-c3ccc(O)cc3)nc12.ClCC1CO1>CO.ClCCl>Cc1cccn2cc(-c3ccc(OCC4CO4)cc3)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-838a0f414b414d4bad70479de4331dc3 | Cc1cccn2cc(-c3ccc(OCC4CO4)cc3)nc12>>CCCNCC(O)COc1ccc(-c2cn3cccc(C)c3n2)cc1 | O1C(COC2=CC=C(C=C2)C=2N=C3N(C=CC=C3C)C2)C1>>OC(COC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1)CNCCC | [cH:1]1[cH:11][c:10]([O:9][CH2:8][CH:6]2[CH2:5][O:7]2)[cH:25][cH:24][c:13]1-[c:14]1[n:4][c:22]2[n:16]([cH:15]1)[cH:17][cH:18][cH:19][c:20]2[CH3:21]>>[CH3:1][CH2:2][CH2:3][NH:4][CH2:5][CH:6]([OH:7])[CH2:8][O:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][n:16]3[cH:17][cH:18][cH:19][c:20]([CH3:21])[c:22]3[n:23]2)[cH:24][c... | Cc1cccn2cc(-c3ccc(OCC4CO4)cc3)nc12 | CCCNCC(O)COc1ccc(-c2cn3cccc(C)c3n2)cc1 | null | null | C(CC)N | Functional Group Addition | OtherReaction | c1fa4b1de46a50b1ef4f74b5af0e52ce254469c112d41f022f241d2db390e3fe | 36a3942562c2028f304a7b4f097e589a1695baad98c0df904b434bc04ee590c8 | c1ccc(-c2cn3ccccc3n2)cc1 | [C;D1;H3:1]-[c:2](:[c:3]):[c;H0;D3;+0:4]1:[n;H0;D2;+0:5]:[c;H0;D3;+0:6](-[c;H0;D3;+0:7]2:[c:8]:[c:9]:[c:10](-[#8:11]-[C:12]-[C:13]3-[CH2;D2;+0:14]-[O;H0;D2;+0:15]-3):[cH;D2;+0:16]:[cH;D2;+0:17]:2):[c:18]:[#7;a:19]:1:[c:20]>>[C;D1;H3:1]-[c:2](:[c:3]):[c;H0;D3;+0:4]1:[#7;a:21]:[c;H0;D3;+0:6](-[c;H0;D3;+0:7]2:[c:22]:[cH;D... | null | [] | null | null | null | null | The product of Step C (5.0 g) and propylamine (20 mL) was heated at 40° C. for 18 hours. The reaction was cooled to ambient temperature evaporated and the residue purified via silica gel chromatography (dichloromethane/methanol) to give the title compound which was converted to a HCl salt upon treatment with HCl/methan... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol.Secondary amine | c1ccccc1.C1CO1.c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | Other | C(CC)N | null | null | Cc1cccn2cc(-c3ccc(OCC4CO4)cc3)nc12>C(CC)N>CCCNCC(O)COc1ccc(-c2cn3cccc(C)c3n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c461a06a26c149e5be97585012d42e5c | C1CCNCC1.Cc1cccn2cc(-c3ccc(NS(=O)(=O)CCCCl)cc3)nc12>>Cc1cccn2cc(-c3ccc(NS(=O)(=O)CCCN4CCCCC4)cc3)nc12 | CC=1C=2N(C=CC1)C=C(N2)C2=CC=C(C=C2)NS(=O)(=O)CCCCl.N1CCCCC1>>CC=1C=2N(C=CC1)C=C(N2)C2=CC=C(C=C2)NS(=O)(=O)CCCN2CCCCC2 | [NH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1.Cl[CH2:19][CH2:18][CH2:17][S:14]([NH:13][c:12]1[cH:11][cH:10][c:9](-[c:8]2[cH:7][n:6]3[cH:5][cH:4][cH:3][c:2]([CH3:1])[c:29]3[n:28]2)[cH:27][cH:26]1)(=[O:15])=[O:16]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6]2[cH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([NH:13][S:14](=[O:15])(=[O... | C1CCNCC1.Cc1cccn2cc(-c3ccc(NS(=O)(=O)CCCCl)cc3)nc12 | Cc1cccn2cc(-c3ccc(NS(=O)(=O)CCCN4CCCCC4)cc3)nc12 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=S(=O)(CCCN1CCCCC1)Nc1ccc(-c2cn3ccccc3n2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | The product of Step A (65 mg) and piperidine (1.0 mL) were heated at 100° C. for 1.5 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (15 mL) and saturated sodium bicarbonate solution (15 mL). The aqueous portion was extracted with a fresh portion of ethyl acetate (15 mL) (2×)... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccn2ccnc2c1.c1ccccc1.C1CC[NH]CC1 | HCl | null | null | null | C1CCNCC1.Cc1cccn2cc(-c3ccc(NS(=O)(=O)CCCCl)cc3)nc12>>Cc1cccn2cc(-c3ccc(NS(=O)(=O)CCCN4CCCCC4)cc3)nc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f23b6d9e5abd4f8d9c2f50a4359ddf11 | CC(=O)OC(C)=O.Nc1ccc(I)cc1>>CC(=O)Nc1ccc(I)cc1 | IC1=CC=C(N)C=C1.C(C)(=O)OC(C)=O.N1=CC=CC=C1>>CC(=O)NC1=CC=C(C=C1)I | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]([I:9])[cH:10][cH:11]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([I:9])[cH:10][cH:11]1 | CC(=O)OC(C)=O.Nc1ccc(I)cc1 | CC(=O)Nc1ccc(I)cc1 | null | null | C(C)(=O)OCC | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 99 | [{"value": 99.0, "product": "CC(=O)NC1=CC=C(C=C1)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.8, "product": "CC(=O)NC1=CC=C(C=C1)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 4-Iodoaniline (11.0 g, 50.4 mmol) was dissolved in 60 mL of ethyl acetate and the solution was added with 10 mL of acetic anhydride (10.8 g, 106 mmol) and 7.8 mL of pyridine (7.65 g, 99.4 mmol), and the mixture was stirred at room temperature for 2 hours with an equipment of a CaCl2 tube. A solvent was evaporated under... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | C(C)(=O)OCC | null | 2 | CC(=O)OC(C)=O.Nc1ccc(I)cc1>C(C)(=O)OCC>CC(=O)Nc1ccc(I)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3c74f0dae9174e5a9b948560c4277649 | C=CCCCCCC>>C=CCCCCCC | C=C.C=CCCCCCC.C(C)=C1C2C=CC(C1)C2.C(C)=C1C2C=CC(C1)C2.[H][H].C=C.FC1=C(C(=C(C(=C1[B-](C1=C(C(=C(C(=C1F)F)F)F)F)(C1=C(C(=C(C(=C1F)F)F)F)F)C1=C(C(=C(C(=C1F)F)F)F)F)F)F)F)F.C[NH+](CCCCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCCCC.C(C)=C1C2C=CC(C1)C2>>C=C.C=CCCCCCC | [CH2:3]=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>>[CH2:3]=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10] | C=CCCCCCC | C=CCCCCCC | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | 130 | CELSIUS | null | null | All liquids except ethylidenenorbornene (ENB) and gas feeds were passed through columns of alumina and a decontaminant (Q-5™ catalyst available from Englehardt Chemicals Inc.) prior to introduction into the reactor. ENB was passed through a short column (3×10 cm) of alumina prior to introduction to the reactor. Catalys... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C1(=CC=CC=C1)C | 130 | null | C=CCCCCCC>C1(=CC=CC=C1)C>C=CCCCCCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d0cdd4fa01f49f6b53d97ccf3b91696 | COC(=N)N.N[C@@H](CSSC[C@H](N)C(=O)O)C(=O)O.[NH4+]>>N=C(N)NC(SSC[C@H](N)C(=O)O)[C@H](N)C(=O)O | C([C@@H](C(=O)O)N)SSC[C@@H](C(=O)O)N.S(=O)(=O)(O)O.COC(N)=N.[OH-].[NH4+]>>N(C(=N)N)C([C@@H](C(=O)O)N)SSC[C@@H](C(=O)O)N | CO[C:2](=[NH:3])[NH2:4].[CH2:5]([S:6][S:7][CH2:8][C@H:9]([NH2:10])[C:11](=[O:12])[OH:13])[C@H:14]([NH2:15])[C:16](=[O:17])[OH:18].[NH4+:1]>>[NH:1]=[C:2]([NH2:3])[NH:4][CH:5]([S:6][S:7][CH2:8][C@H:9]([NH2:10])[C:11](=[O:12])[OH:13])[C@H:14]([NH2:15])[C:16](=[O:17])[OH:18] | COC(=N)N.N[C@@H](CSSC[C@H](N)C(=O)O)C(=O)O.[NH4+] | N=C(N)NC(SSC[C@H](N)C(=O)O)[C@H](N)C(=O)O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 373c7bd4e08a01e3a77bece59caac21b8b46b97c32f64c35f9954632a004b442 | 6420dd724a727dc91eddb7b7ab11cf05df5a2d619d8d355c94d4b9a20938e740 | null | C-O-[C;H0;D3;+0:1](-[NH2;D1;+0:2])=[NH;D1;+0:3].[#16:4]-[#16:5]-[CH2;D2;+0:6]-[C:7](-[N;D1;H2:8])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11].[NH4+;D0:12]>>[#16:4]-[#16:5]-[CH;D3;+0:6](-[NH;D2;+0:2]-[C;H0;D3;+0:1](-[NH2;D1;+0:3])=[NH;D1;+0:12])-[C:7](-[N;D1;H2:8])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11] | null | [] | 60 | CELSIUS | null | null | To a solution of cystine (1 gm, 4.2 mmol) in ammonium hydroxide (10 mL) in a screw-capped vial was added O-methylisourea hydrogen sulfate (1.8 gm, 10 mmol). The vial was sealed and heated to 60° C. for 16 h. The solution was then cooled and the ammonium hydroxide was removed by rotary evaporation. The solid was then di... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Primary amine.Secondary amine | null | null | null | HO- | null | 60 | null | COC(=N)N.N[C@@H](CSSC[C@H](N)C(=O)O)C(=O)O.[NH4+]>>N=C(N)NC(SSC[C@H](N)C(=O)O)[C@H](N)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cbdb9df44d244fdc8371bcf42b84aa10 | CC(O)C(=O)c1ccccc1.CI>>COC(C)C(=O)c1ccccc1 | OC(C(=O)C1=CC=CC=C1)C.IC.C(=O)([O-])[O-].[K+].[K+]>>COC(C(=O)C1=CC=CC=C1)C | [OH:2][CH:3]([CH3:4])[C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.I[CH3:1]>>[CH3:1][O:2][CH:3]([CH3:4])[C:5](=[O:6])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | CC(O)C(=O)c1ccccc1.CI | COC(C)C(=O)c1ccccc1 | null | null | CC(=O)C.C(C)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 31ec8f945a35f4f87287620e27b68692ce42732551035fbac056df61d9acce14 | 08f7221cae607d413f579138dcaa6997bebcad2bbb42d2f1b3b2a2d886befb37 | c1ccccc1 | I-[CH3;D1;+0:1].[C;D1;H3:2]-[C:3](-[OH;D1;+0:4])-[C:5](=[O;D1;H0:6])-[c:7]>>[C;D1;H3:2]-[C:3](-[O;H0;D2;+0:4]-[CH3;D1;+0:1])-[C:5](=[O;D1;H0:6])-[c:7] | null | [] | null | null | null | null | A mixture of 2-hydroxypropiophenone (3.00 g, 20.0 mmol), iodomethane (3.40 g, 24.0 mmol), and K2CO3 (granular, anh.; 13.8 g, 99.9 mmol) was refluxed in acetone (75 mL) for 18 h. The reaction mixture was cooled to room temperature and the inorganic salts were removed by filtration. The filtrate was evaporated under vacu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ether | null | null | c1ccccc1 | HI | CC(=O)C.C(C)OCC | null | null | CC(O)C(=O)c1ccccc1.CI>CC(=O)C.C(C)OCC>COC(C)C(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-059b828bdb38424794d4aa280bc1785d | O[C@@H](CCCl)c1ccccc1.Oc1cccc(F)c1>>Fc1cccc(O[C@H](CCCl)c2ccccc2)c1 | CNCCC(C=1C=CC=CC1)OC=2C=CC(=CC2)C(F)(F)F.ClCC[C@H](O)C1=CC=CC=C1.FC=1C=C(C=CC1)O.N(=NC(=O)OCC)C(=O)OCC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>FC=1C=C(O[C@H](CCCl)C2=CC=CC=C2)C=CC1 | O[C@@H:8]([CH2:9][CH2:10][Cl:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([OH:7])[cH:18]1>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][C@H:8]([CH2:9][CH2:10][Cl:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18]1 | O[C@@H](CCCl)c1ccccc1.Oc1cccc(F)c1 | Fc1cccc(O[C@H](CCCl)c2ccccc2)c1 | null | null | C1CCOC1.C(C)OCC | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | aee3d691a6dfc6c8223fef7b9bb4e58ec7e16fbc345d424207a131929cdf1d03 | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1ccc(COc2ccccc2)cc1 | O-[C@@H;D3;+0:1](-[C:2]-[C:3])-[c:4](:[c:5]):[c:6].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C:3]-[C:2]-[C@@H;D3;+0:1](-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10])-[c:4](:[c:5]):[c:6] | 15.7 | [{"value": 15.7, "product": "FC=1C=C(O[C@H](CCCl)C2=CC=CC=C2)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.7, "product": "FC=1C=C(O[C@H](CCCl)C2=CC=CC=C2)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 18 | HOUR | Following a similar procedure for the chiral synthesis of fluoxetine [Srebnik, M. et al., J. Org. Chem. 25 53(13), 2916–20 (1988), hereby incorporated by reference herein], a solution of (S)-(−)3-chloro-1-phenyl-1-propanol (4.00 g, 23.4 mmol), 3-fluorophenol (2.63 g, 23.4 mmol), and diethyl azodicarboxylate (4.00 g, 23... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1 | HO- | C1CCOC1.C(C)OCC | 0 | 18 | O[C@@H](CCCl)c1ccccc1.Oc1cccc(F)c1>C1CCOC1.C(C)OCC>Fc1cccc(O[C@H](CCCl)c2ccccc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-abc62c4c493348adbd97077bae5dbf05 | Fc1cccc(O[C@H](CCCl)c2ccccc2)c1.[NH4+]>>NCC[C@@H](Oc1cccc(F)c1)c1ccccc1 | FC=1C=C(O[C@H](CCCl)C2=CC=CC=C2)C=CC1.[NH4+].[OH-].CCO.C(\C=C/C(=O)O)(=O)O>>FC=1C=C(O[C@H](CCN)C2=CC=CC=C2)C=CC1 | Cl[CH2:2][CH2:3][C@@H:4]([O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([F:11])[cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.[NH4+:1]>>[NH2:1][CH2:2][CH2:3][C@@H:4]([O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([F:11])[cH:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | Fc1cccc(O[C@H](CCCl)c2ccccc2)c1.[NH4+] | NCC[C@@H](Oc1cccc(F)c1)c1ccccc1 | null | null | CCOC(=O)C.C(C)#N | Functional Group Interconversion | OtherReaction | 4b60b38199c5e1c6265f0f00cb816ce522bef9386a0afaaa1b73d5504b655ff2 | ae87d719fccf317757aefe22b7505f050f2863a1ec19f3087f5f21097b5e15a5 | c1ccc(COc2ccccc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[NH4+;D0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH2;D1;+0:4] | null | [] | null | null | null | null | A solution of (R)-3-(3-fluorophenoxy)-3-phenylpropyl chloride (0.971 g, 3.96 mmol), conc. NH4OH (30 mL), and EtOH (20 mL) were shaken at 90° C. on a Parr apparatus (50–90 psig) for 18 h. The mixture was then evaporated under vacuum and the residue was dissolved in Et2O (100 mL) and washed with H2O (2×25 mL). The organi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Primary amine | null | null | c1ccccc1.c1ccccc1 | HCl | CCOC(=O)C.C(C)#N | null | null | Fc1cccc(O[C@H](CCCl)c2ccccc2)c1.[NH4+]>CCOC(=O)C.C(C)#N>NCC[C@@H](Oc1cccc(F)c1)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8b373ac0387f4214a1526b9b4b83818b | Cc1ccc(F)cc1C#N.O=C1CCC(=O)N1Br>>N#Cc1cc(F)ccc1CBr | FC=1C=CC(=C(C#N)C1)C.BrN1C(CCC1=O)=O>>BrCC1=C(C#N)C=C(C=C1)F | [N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[CH3:10].O=C1CCC(=O)N1[Br:11]>>[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[CH2:10][Br:11] | Cc1ccc(F)cc1C#N.O=C1CCC(=O)N1Br | N#Cc1cc(F)ccc1CBr | null | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 102 | [{"value": 102.0, "product": "BrCC1=C(C#N)C=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.7, "product": "BrCC1=C(C#N)C=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5-fluoro-2-methylbenzonitrile (10.0 g, 74.0 mmol), N-bromosuccinimide (NBS, 13.2 g, 74.0 mmol), benzoyl peroxide (0.2 g, 0.82 mmol), and carbon tetrachloride (100 mL) was refluxed for 18 h. The reaction mixture was then cooled to room temperature and filtered through fritted glass. The solid in the funnel ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(Cl)(Cl)(Cl)Cl | null | null | Cc1ccc(F)cc1C#N.O=C1CCC(=O)N1Br>C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(Cl)(Cl)(Cl)Cl>N#Cc1cc(F)ccc1CBr |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b1ca4ad206c7491da2afea1c84001543 | CCC(CC)(O[PH](=O)[O-])c1ccc(F)cc1C#N.O=Cc1ccc(F)cc1>>N#Cc1cc(F)ccc1C=Cc1ccc(F)cc1 | [Na+].[Cl-].[H-].[Na+].P(OC(C1=C(C=C(C=C1)F)C#N)(CC)CC)([O-])=O.FC1=CC=C(C=O)C=C1>>FC1=CC=C(C=C1)C=CC1=C(C#N)C=C(C=C1)F | CC[C:10](CC)(O[PH](=O)[O-])[c:9]1[c:3]([C:2]#[N:1])[cH:4][c:5]([F:6])[cH:7][cH:8]1.O=[CH:11][c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[CH:10]=[CH:11][c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1 | CCC(CC)(O[PH](=O)[O-])c1ccc(F)cc1C#N.O=Cc1ccc(F)cc1 | N#Cc1cc(F)ccc1C=Cc1ccc(F)cc1 | null | null | O.CN(C)C=O | C-C Coupling | OtherReaction | 43d4e2f03e758941ee99f59641d5d56e6475fe935434d251d75d5cdebbe19869 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=Cc1ccccc1)c1ccccc1 | C-C-[C;H0;D4;+0:1](-C-C)(-O-[PH](=O)-[O-])-[c:2](:[c:3]):[c:4].O=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[CH;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 23.2 | [{"value": 23.2, "product": "FC1=CC=C(C=C1)C=CC1=C(C#N)C=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.2, "product": "FC1=CC=C(C=C1)C=CC1=C(C#N)C=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Sodium hydride (60% in mineral oil; 1.66 g [0.993 g NaH], 1.4 mmol, 1.10 equiv) was added to a solution of diethyl-2-cyano-4-fluorobenzyl phosphonate (10.2 g-equiv, 37.6 mmol, 1.0 equiv) in DMF (40 mL) over a period of 2 min. The reaction was stirred for 20 min at room temperature. 4-Fluorobenzaldehyde (4.67 g, 38 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | null | null | c1ccccc1.c1ccccc1 | HO- | O.CN(C)C=O | null | 0.333333 | CCC(CC)(O[PH](=O)[O-])c1ccc(F)cc1C#N.O=Cc1ccc(F)cc1>O.CN(C)C=O>N#Cc1cc(F)ccc1C=Cc1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aab5917117c346febea6a78881833188 | N#Cc1cc(F)ccc1C=Cc1ccc(F)cc1>>N#Cc1cc(F)ccc1CCc1ccc(F)cc1 | FC1=CC=C(C=C1)C=CC1=C(C#N)C=C(C=C1)F>>FC1=CC=C(C=C1)CCC1=C(C#N)C=C(C=C1)F | [N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[CH:10]=[CH:11][c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[CH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1 | N#Cc1cc(F)ccc1C=Cc1ccc(F)cc1 | N#Cc1cc(F)ccc1CCc1ccc(F)cc1 | null | [Pd] | COCCOC | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(CCc2ccccc2)cc1 | [c:1]:[c:2](-[CH;D2;+0:3]=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8]>>[c:1]:[c:2](-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7]):[c:8] | 99.2 | [{"value": 99.0, "product": "FC1=CC=C(C=C1)CCC1=C(C#N)C=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.2, "product": "FC1=CC=C(C=C1)CCC1=C(C#N)C=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2-[2-(4-Fluorophenyl)ethenyl]-5-fluorobenzonitrile (2.1 g, 8.7 mmol) was dissolved in ethylene glycol dimethyl ether (100 mL). Palladium on charcoal (10% Pd; 0.20 g) was added, and the reaction mixture was shaken under 60 psig H2 for 1 h. The reaction mixture was then filtered through Celite®, and the filtrate was rota... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1 | null | [Pd].COCCOC | null | 1 | N#Cc1cc(F)ccc1C=Cc1ccc(F)cc1>[Pd].COCCOC>N#Cc1cc(F)ccc1CCc1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-46f23c8aa8a04871bdab7af10a51daaf | N#Cc1cc(F)ccc1CCc1ccc(F)cc1.O.[OH-]>>O=C(O)c1cc(F)ccc1CCc1ccc(F)cc1 | Cl.FC1=CC=C(C=C1)CCC1=C(C#N)C=C(C=C1)F.[OH-].[Na+].O>>FC1=CC=C(C=C1)CCC1=C(C(=O)O)C=C(C=C1)F | N#[C:2][c:4]1[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]1[CH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1.[OH2:1].[OH-:3]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([F:7])[cH:8][cH:9][c:10]1[CH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1 | N#Cc1cc(F)ccc1CCc1ccc(F)cc1.O.[OH-] | O=C(O)c1cc(F)ccc1CCc1ccc(F)cc1 | null | null | C(CO)O | Acylation | OtherReaction | e05c34ebe51fe654c61f91bb118ee544dcd0a035df9f073c07f2e1b77a1f299a | e722778fc7d66899e0f2f256942c8c213a77617f32bb1410d97747833c62e260 | c1ccc(CCc2ccccc2)cc1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH-;D0:5].[OH2;D0;+0:6]>>[O;H0;D1;+0:6]=[C;H0;D3;+0:1](-[OH;D1;+0:5])-[c:2](:[c:3]):[c:4] | 88.4 | [{"value": 88.4, "product": "FC1=CC=C(C=C1)CCC1=C(C(=O)O)C=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | 190 | CELSIUS | null | null | A mixture of 2-[2-(4-fluorophenyl)ethyl]-5-fluorobenzonitrile (2.12 g, 8.72 mmol, 1 equiv) and aq. NaOH (10N; 3.9 mL, 39.3 mmol, 4.5 equiv) in ethylene glycol (25 mL) was heated at 190° C. for 24 h. After allowing the mixture to cool, H2O (100 mL) was added followed by 12N HCl (8 mL). The cloudy mixture precipitated th... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | C(CO)O | 190 | null | N#Cc1cc(F)ccc1CCc1ccc(F)cc1.O.[OH-]>C(CO)O>O=C(O)c1cc(F)ccc1CCc1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d715ecfdb67a41a48509fd54ef0d2331 | O=C(O)c1cc(F)ccc1CCc1ccc(F)cc1>>O=C1c2cc(F)ccc2CCc2ccc(F)cc21 | [Cl-].[Al+3].[Cl-].[Cl-].FC1=CC=C(C=C1)CCC1=C(C(=O)O)C=C(C=C1)F.C(C(=O)Cl)(=O)Cl>>FC=1C=CC2=C(C(C3=C(CC2)C=CC(=C3)F)=O)C1 | O[C:2](=[O:1])[c:3]1[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]1[CH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1>>[O:1]=[C:2]1[c:3]2[cH:4][c:5]([F:6])[cH:7][cH:8][c:9]2[CH2:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][c:18]21 | O=C(O)c1cc(F)ccc1CCc1ccc(F)cc1 | O=C1c2cc(F)ccc2CCc2ccc(F)cc21 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 611168eee050a88dfe59513ec0572b8b402942d32cf1ab7ce65848aca3a001bb | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | O=C1c2ccccc2CCc2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[C:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](:[c:10]:[c:11])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 85 | [{"value": 85.0, "product": "FC=1C=CC2=C(C(C3=C(CC2)C=CC(=C3)F)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-[2-(4-fluorophenyl)ethyl]-5-fluorobenzoic acid (2.02 g, 7.71 mmol, 1 equiv) and oxalyl chloride (1.37 g, 10.8 mmol, 1.4 equiv) in CH2Cl2 (20 mL) was refluxed for 30 min. The resulting solution was then added to a stirring suspension of aluminum chloride (1.44 g, 10.8 mmol, 1.4 equiv) in CH2Cl2 (50 mL). T... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccc2c(c1)CCc1ccccc1C2 | c1ccc2c(c1)CCc1ccccc1C2 | HO- | C(Cl)Cl | null | null | O=C(O)c1cc(F)ccc1CCc1ccc(F)cc1>C(Cl)Cl>O=C1c2cc(F)ccc2CCc2ccc(F)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4debe123c0e647088929ba120d5af46f | N#Cc1ccccc1CCc1ccc(F)cc1.O.[OH-]>>O=C(O)c1ccccc1CCc1ccc(F)cc1 | Cl.FC1=CC=C(C=C1)CCC1=C(C#N)C=CC=C1.[OH-].[Na+].O>>FC1=CC=C(C=C1)CCC1=C(C(=O)O)C=CC=C1 | N#[C:2][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[CH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1.[OH2:1].[OH-:3]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[CH2:10][CH2:11][c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1 | N#Cc1ccccc1CCc1ccc(F)cc1.O.[OH-] | O=C(O)c1ccccc1CCc1ccc(F)cc1 | null | null | C(CO)O | Acylation | OtherReaction | e05c34ebe51fe654c61f91bb118ee544dcd0a035df9f073c07f2e1b77a1f299a | e722778fc7d66899e0f2f256942c8c213a77617f32bb1410d97747833c62e260 | c1ccc(CCc2ccccc2)cc1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH-;D0:5].[OH2;D0;+0:6]>>[O;H0;D1;+0:6]=[C;H0;D3;+0:1](-[OH;D1;+0:5])-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A mixture of 2-[2-(4-fluorophenyl)ethyl]benzonitrile (8.03 g, 35.6 mmol, 1 equiv) and aq. NaOH (10N; 16 mL, 160 mmol, 4.5 equiv) in ethylene glycol (100 mL) was heated to 190 C for 69 h. After allowing the reaction mixture to cool, H2O (300 mL) was added, followed by 12N HCl (16 mL). This mixture was extracted with CHC... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Carboxylic acid | null | null | c1ccccc1.c1ccccc1 | Other | C(CO)O | null | null | N#Cc1ccccc1CCc1ccc(F)cc1.O.[OH-]>C(CO)O>O=C(O)c1ccccc1CCc1ccc(F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f2d910d7234a4477bb0c1e7dddb48908 | O=C(O)c1ccccc1CCc1ccc(F)cc1>>O=C1c2ccccc2CCc2ccc(F)cc21 | [Cl-].[Al+3].[Cl-].[Cl-].FC1=CC=C(C=C1)CCC1=C(C(=O)O)C=CC=C1.C(C(=O)Cl)(=O)Cl>>FC=1C=CC2=C(C(C3=C(CC2)C=CC=C3)=O)C1 | O[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][CH2:10][c:11]2[cH:12][cH:13][c:14]([F:15])[cH:16][c:17]21 | O=C(O)c1ccccc1CCc1ccc(F)cc1 | O=C1c2ccccc2CCc2ccc(F)cc21 | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 611168eee050a88dfe59513ec0572b8b402942d32cf1ab7ce65848aca3a001bb | 6a71bb5a71b59feeb4f6a39b1b66fa450a058b64b0a3909e1a51c22473a141c5 | O=C1c2ccccc2CCc2ccccc21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[C:6]-[c:7](:[c:8]):[c;H0;D3;+0:9](:[c:10]:[c:11])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 99.7 | [{"value": 99.7, "product": "FC=1C=CC2=C(C(C3=C(CC2)C=CC=C3)=O)C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-[2-(4-fluorophenyl)ethyl]benzoic acid (4.00 g, 16.4 mmol, 1 equiv) and oxalyl chloride (2.0 mL, 2.9 g, 23 mmol, 1.4 equiv) in CH2Cl2 (50 mL) was refluxed for 30 min. The resulting solution was then added to a stirring suspension of aluminum chloride (3.0 g, 2.2 mmol, 1.4 equiv) in CH2Cl2 (50 mL). This mi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccccc1 | c1ccc2c(c1)CCc1ccccc1C2 | c1ccc2c(c1)CCc1ccccc1C2 | HO- | C(Cl)Cl | null | null | O=C(O)c1ccccc1CCc1ccc(F)cc1>C(Cl)Cl>O=C1c2ccccc2CCc2ccc(F)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fc08a00bc9a040b3a45a8e40ce7d7458 | CC(C)(C)S.Clc1cc(Cl)cc(Cl)c1>>CC(C)(Cc1cc(Cl)cc(Cl)c1)SC(C)(C)Cc1cc(Cl)cc(Cl)c1 | ClC1=CC(=CC(=C1)Cl)Cl.[OH-].[Na+].C(C)(C)(C)S>>ClC=1C=C(C=C(C1)Cl)CC(C)(C)SC(CC1=CC(=CC(=C1)Cl)Cl)(C)C | [CH3:1][C:2]([CH3:9])([CH3:10])[SH:13].[c:5]1([Cl:21])[cH:6][c:14]([Cl:8])[cH:25][c:23]([Cl:24])[cH:22]1>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][c:7]([Cl:8])[cH:9][c:10]([Cl:11])[cH:12]1)[S:13][C:14]([CH3:15])([CH3:16])[CH2:17][c:18]1[cH:19][c:20]([Cl:21])[cH:22][c:23]([Cl:24])[cH:25]1 | CC(C)(C)S.Clc1cc(Cl)cc(Cl)c1 | CC(C)(Cc1cc(Cl)cc(Cl)c1)SC(C)(C)Cc1cc(Cl)cc(Cl)c1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | null | Aromatic Heterocycle Formation | OtherReaction | 1dba0b8ead539332d4b58f97a2ae879a4255f03bcb8b1fad5c0f5cb3f34fe6cf | 8a46a2aeb20151a50f7a0b895c51ca25a6abdce5c315b62f9f2b6b429b45b7bb | c1ccc(CCSCCc2ccccc2)cc1 | [C;D1;H3:1]-[C;H0;D4;+0:2](-[CH3;D1;+0:3])(-[CH3;D1;+0:4])-[SH;D1;+0:5].[Cl;D1;H0:6]-[c:7]1:[cH;D2;+0:8]:[c;H0;D3;+0:9](-[Cl;H0;D1;+0:10]):[cH;D2;+0:11]:[c;H0;D3;+0:12](-[Cl;H0;D1;+0:13]):[cH;D2;+0:14]:1>>[C;D1;H3:15]-[C;H0;D4;+0:12](-[C;D1;H3:16])(-[C:17]-[c:18]1:[c:19]:[c:20](-[Cl;H0;D1;+0:10]):[cH;D2;+0:8]:[c:7](-[C... | 19 | [{"value": 19.0, "product": "ClC=1C=C(C=C(C1)Cl)CC(C)(C)SC(CC1=CC(=CC(=C1)Cl)Cl)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of 4N sodium hydroxide (0.8 ml) was added tert-butylmercaptan (0.406 ml). The mixture was stirred for 15 minutes at room temperature. Tetra n-butylammonium bromide (322 mg, 1 mmol) and 1,3,5-trichlorobenzene (1) (1.8 g, 10 mmol) were added thereto. The reaction mixture was refluxed at 140° C. for 6.5 hour... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aliphatic thiol | Aromatic halide.Aromatic halide.Aromatic halide.Monosulfide | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Other | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | null | 0.25 | CC(C)(C)S.Clc1cc(Cl)cc(Cl)c1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC>CC(C)(Cc1cc(Cl)cc(Cl)c1)SC(C)(C)Cc1cc(Cl)cc(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2f0a2acc9ff04ce9970e759f6806a4ac | CC(C)(C)S.Clc1cc(Cl)cc(Cl)c1>>CC(C)(Cc1cc(Cl)cc(Cl)c1)SC(C)(C)Cc1cc(Cl)cc(Cl)c1 | ClC1=CC(=CC(=C1)Cl)Cl.[OH-].[Na+].C(C)(C)(C)S>>ClC=1C=C(C=C(C1)Cl)CC(C)(C)SC(CC1=CC(=CC(=C1)Cl)Cl)(C)C | [CH3:1][C:2]([CH3:9])([CH3:10])[SH:13].[c:5]1([Cl:21])[cH:6][c:14]([Cl:8])[cH:25][c:23]([Cl:24])[cH:22]1>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][c:7]([Cl:8])[cH:9][c:10]([Cl:11])[cH:12]1)[S:13][C:14]([CH3:15])([CH3:16])[CH2:17][c:18]1[cH:19][c:20]([Cl:21])[cH:22][c:23]([Cl:24])[cH:25]1 | CC(C)(C)S.Clc1cc(Cl)cc(Cl)c1 | CC(C)(Cc1cc(Cl)cc(Cl)c1)SC(C)(C)Cc1cc(Cl)cc(Cl)c1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 1dba0b8ead539332d4b58f97a2ae879a4255f03bcb8b1fad5c0f5cb3f34fe6cf | 8a46a2aeb20151a50f7a0b895c51ca25a6abdce5c315b62f9f2b6b429b45b7bb | c1ccc(CCSCCc2ccccc2)cc1 | [C;D1;H3:1]-[C;H0;D4;+0:2](-[CH3;D1;+0:3])(-[CH3;D1;+0:4])-[SH;D1;+0:5].[Cl;D1;H0:6]-[c:7]1:[cH;D2;+0:8]:[c;H0;D3;+0:9](-[Cl;H0;D1;+0:10]):[cH;D2;+0:11]:[c;H0;D3;+0:12](-[Cl;H0;D1;+0:13]):[cH;D2;+0:14]:1>>[C;D1;H3:15]-[C;H0;D4;+0:12](-[C;D1;H3:16])(-[C:17]-[c:18]1:[c:19]:[c:20](-[Cl;H0;D1;+0:10]):[cH;D2;+0:8]:[c:7](-[C... | 41 | [{"value": 41.0, "product": "ClC=1C=C(C=C(C1)Cl)CC(C)(C)SC(CC1=CC(=CC(=C1)Cl)Cl)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of sodium hydroxide (120 mg, 3 mmol, in oil, 60% cont.) in anhydrous methanol (5 ml) was added tert-butyl mercaptan (0.406 ml). The mixture was stirred for 20 minutes at room temperature. The reaction mixture was concentrated dryness under reduced pressure. The obtained sodium isopropylmercaptan was disso... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aliphatic thiol | Aromatic halide.Aromatic halide.Aromatic halide.Monosulfide | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Other | CO | null | 0.333333 | CC(C)(C)S.Clc1cc(Cl)cc(Cl)c1>CO>CC(C)(Cc1cc(Cl)cc(Cl)c1)SC(C)(C)Cc1cc(Cl)cc(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d703faf9a4724073854aea47b7f469a8 | CC(C)c1c[nH]c(COCc2ccccc2)n1.ClSc1cc(Cl)cc(Cl)c1>>CC(C)c1nc(COCc2ccccc2)[nH]c1Sc1cc(Cl)cc(Cl)c1 | C(C1=CC=CC=C1)OCC=1NC=C(N1)C(C)C.C(C)N(CC)CC.O.ClC=1C=C(C=C(C1)Cl)SCl>>C(C1=CC=CC=C1)OCC=1NC(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl | [CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([CH2:7][O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[nH:16][cH:17]1.Cl[S:18][c:19]1[cH:20][c:21]([Cl:22])[cH:23][c:24]([Cl:25])[cH:26]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([CH2:7][O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[nH:16][c:17]1[S:18][c:19]1[cH:... | CC(C)c1c[nH]c(COCc2ccccc2)n1.ClSc1cc(Cl)cc(Cl)c1 | CC(C)c1nc(COCc2ccccc2)[nH]c1Sc1cc(Cl)cc(Cl)c1 | null | null | C(C)#N.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | a27b3294137f5604f3e4a02b9914786239987b987901dc64910b2c4e71e89f1b | 1d56361848b170d7aeb1292e5d4a0c5a5f2486eaf968085176af0d58840010a8 | c1ccc(COCc2ncc(Sc3ccccc3)[nH]2)cc1 | Cl-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[c:6]1:[#7;a:7]:[c:8](-[C:9]):[#7;a:10]:[cH;D2;+0:11]:1>>[C:5]-[c:6]1:[#7;a:7]:[c:8](-[C:9]):[#7;a:10]:[c;H0;D3;+0:11]:1-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | 82 | [{"value": 82.0, "product": "C(C1=CC=CC=C1)OCC=1NC(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.8, "product": "C(C1=CC=CC=C1)OCC=1NC(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 2-Benzyloxymethyl-4-isopropyl-1H-imidazole (7) (550 mg, 2.4 mmol), described as Reference Example 1 of WO 96/10019 was dissolved in a mixture of triethylamine 360 mg (3.6 mmol) and acetonitrile 4 ml. To the solution was added 3,5-dichlorobenzenesulfenyl chloride (3) 930 mg (4.4 mmol) at room temperature. The mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Monosulfide | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1.c1ccccc1 | HCl | C(C)#N.C1(=CC=CC=C1)C | null | 0.5 | CC(C)c1c[nH]c(COCc2ccccc2)n1.ClSc1cc(Cl)cc(Cl)c1>C(C)#N.C1(=CC=CC=C1)C>CC(C)c1nc(COCc2ccccc2)[nH]c1Sc1cc(Cl)cc(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-58ca58da0f794be99a415fb53af683dc | CC(C)c1cn(-c2ccncc2)c(COCc2ccccc2)n1.CCN(CC)CC.ClSc1cc(Cl)cc(Cl)c1>>CC(C)c1nc(COCc2ccccc2)n(Cc2ccncc2)c1Sc1cc(Cl)cc(Cl)c1 | O.C(C1=CC=CC=C1)OCC=1N(C=C(N1)C(C)C)C1=CC=NC=C1.ClC=1C=C(C=C(C1)Cl)SCl.C(C)N(CC)CC>>C(C1=CC=CC=C1)OCC=1N(C(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl)CC1=CC=NC=C1 | [CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([CH2:7][O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16](-[c:18]2[cH:19][cH:20][n:21][cH:22][cH:23]2)[cH:24]1.CCN(CC)C[CH3:17].Cl[S:25][c:26]1[cH:27][c:28]([Cl:29])[cH:30][c:31]([Cl:32])[cH:33]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([CH2:7][O:8][CH2:9][c:10]2[cH:11]... | CC(C)c1cn(-c2ccncc2)c(COCc2ccccc2)n1.CCN(CC)CC.ClSc1cc(Cl)cc(Cl)c1 | CC(C)c1nc(COCc2ccccc2)n(Cc2ccncc2)c1Sc1cc(Cl)cc(Cl)c1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | b48c8829a5b8dec1a39665e33dc4866777620cbdcb423e087e926191934ec764 | 767e871706dc009151ee30f93d289a0633dff06530bbb2ce94b89db7fbb3becd | c1ccc(COCc2ncc(Sc3ccccc3)n2Cc2ccncc2)cc1 | C-C-N(-C-C)-C-[CH3;D1;+0:1].Cl-[S;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[C:6]-[c:7]1:[#7;a:8]:[c:9](-[C:10]):[n;H0;D3;+0:11](-[c;H0;D3;+0:12]2:[c:13]:[c:14]:[#7;a:15]:[c:16]:[c:17]:2):[cH;D2;+0:18]:1>>[C:6]-[c:7]1:[#7;a:8]:[c:9](-[C:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[c;H0;D3;+0:12]2:[c:13]:[c:14]:[#7;a:15]:[c:16]:[c:17]:2)... | 81.3 | [{"value": 81.3, "product": "C(C1=CC=CC=C1)OCC=1N(C(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl)CC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.3, "product": "C(C1=CC=CC=C1)OCC=1N(C(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl)CC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | 2-Benzyloxymethyl-4-isopropyl-1-(pyridin-4-yl)-1H-imidazole (5) (10.0 g, 31.1 mmol) was dissolved in toluene (50 ml). The solution was added dropwise to a solution of 3,5-dichlorobenzenesulfenyl chloride (3) (8.0 g, 37.05 mmol) in toluene (24.7 g) under ice-cooling for 30 minutes. To the mixture was added dropwise trie... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine.Monosulfide | Monosulfide | c1cnc[nH]1.c1ccncc1 | c1c[nH]cn1.c1ccncc1 | c1c[nH]cn1.c1ccccc1.c1ccncc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | 1.5 | CC(C)c1cn(-c2ccncc2)c(COCc2ccccc2)n1.CCN(CC)CC.ClSc1cc(Cl)cc(Cl)c1>C1(=CC=CC=C1)C>CC(C)c1nc(COCc2ccccc2)n(Cc2ccncc2)c1Sc1cc(Cl)cc(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-817f567d751f49859e698e37d51e69b5 | CC(C)c1cn(-c2ccncc2)c(COCc2ccccc2)n1>>CC(C)c1cn(-c2ccncc2)c(CO)n1 | C(C1=CC=CC=C1)OCC=1N(C=C(N1)C(C)C)C1=CC=NC=C1.O.C1(=CC=CC=C1)C>>OCC=1N(C=C(N1)C(C)C)C1=CC=NC=C1 | c1ccc(C[O:15][CH2:14][c:13]2[n:6](-[c:7]3[cH:8][cH:9][n:10][cH:11][cH:12]3)[cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[n:16]2)cc1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][n:6](-[c:7]2[cH:8][cH:9][n:10][cH:11][cH:12]2)[c:13]([CH2:14][OH:15])[n:16]1 | CC(C)c1cn(-c2ccncc2)c(COCc2ccccc2)n1 | CC(C)c1cn(-c2ccncc2)c(CO)n1 | null | null | Cl | Deprotection | Hydroxyl benzyl deprotection | c8a6fd2e05b2d36256c76b73aaf4118f20eb14abce1c0289b554265e30b218aa | 29a81fd08d26edc3da6d72c4958026f5af2119326dc1b4714ee5be1c41835609 | c1cc(-n2ccnc2)ccn1 | [#7;a:1]:[c:2](-[C:3]-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1):[#7;a:5]>>[#7;a:1]:[c:2](-[C:3]-[OH;D1;+0:4]):[#7;a:5] | 86.6 | [{"value": 81.4, "product": "OCC=1N(C=C(N1)C(C)C)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.6, "product": "OCC=1N(C=C(N1)C(C)C)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 1 | HOUR | The compound (5) (20.0 g, 62.2 mmol) was suspended in 35% aqueous hydrochloric acid (100 ml). The solution was heated at 85° C. and stirred for 1 hour. The reaction mixture was cooled down to room temperature and water (100 ml) and toluene (44 ml) were added thereto with stirring. The aqueous layer was separated and ne... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol | c1ccccc1 | null | c1c[nH]cn1.c1ccncc1 | Other | Cl | 85 | 1 | CC(C)c1cn(-c2ccncc2)c(COCc2ccccc2)n1>Cl>CC(C)c1cn(-c2ccncc2)c(CO)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1b1cbabccb3541bf91aad69e89164acf | CC(=O)OCc1nc(C(C)C)cn1Cc1ccncc1.ClSc1cc(Cl)cc(Cl)c1>>CC(=O)OCc1nc(C(C)C)c(Sc2cc(Cl)cc(Cl)c2)n1Cc1ccncc1 | ClC=1C=C(C=C(C1)Cl)SCl.C(C)(=O)OCC=1N(C=C(N1)C(C)C)CC1=CC=NC=C1.C(C)N(CC)CC>>C(C)(=O)OCC=1N(C(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl)CC1=CC=NC=C1 | [CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[n:7][c:8]([CH:9]([CH3:10])[CH3:11])[cH:12][n:22]1[CH2:23][c:24]1[cH:25][cH:26][n:27][cH:28][cH:29]1.Cl[S:13][c:14]1[cH:15][c:16]([Cl:17])[cH:18][c:19]([Cl:20])[cH:21]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[n:7][c:8]([CH:9]([CH3:10])[CH3:11])[c:12]([S:13][c:14]2[cH:15][c:16]([Cl:... | CC(=O)OCc1nc(C(C)C)cn1Cc1ccncc1.ClSc1cc(Cl)cc(Cl)c1 | CC(=O)OCc1nc(C(C)C)c(Sc2cc(Cl)cc(Cl)c2)n1Cc1ccncc1 | null | null | C(C)#N.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 690eacd6c22fa21bb9792e4a2d7611543d6c69bb14eb007ea9f8411f0786da2b | 1d56361848b170d7aeb1292e5d4a0c5a5f2486eaf968085176af0d58840010a8 | c1ccc(Sc2cncn2Cc2ccncc2)cc1 | Cl-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7;a:6]1:[cH;D2;+0:7]:[c:8](-[C:9]):[#7;a:10]:[c:11]:1-[C:12]>>[C:5]-[#7;a:6]1:[c:11](-[C:12]):[#7;a:10]:[c:8](-[C:9]):[c;H0;D3;+0:7]:1-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | 82 | [{"value": 82.0, "product": "C(C)(=O)OCC=1N(C(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl)CC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.2, "product": "C(C)(=O)OCC=1N(C(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl)CC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of the compound (3) (0.97 g, 4.5 mmol) in toluene (1.88 g) was added dropwise a solution of the compound (10a) (0.87 g, 3.2 mmol) in acetonitrile (4 ml) under ice-cooling for 30 minutes. A solution of triethylamine (0.46 g, 4.5 mmol) in acetonitrile (0.5 ml) was added dropwise thereto for 15 minutes, and ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Monosulfide | c1cnc[nH]1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccccc1.c1ccncc1 | HCl | C(C)#N.C1(=CC=CC=C1)C | null | 0.25 | CC(=O)OCc1nc(C(C)C)cn1Cc1ccncc1.ClSc1cc(Cl)cc(Cl)c1>C(C)#N.C1(=CC=CC=C1)C>CC(=O)OCc1nc(C(C)C)c(Sc2cc(Cl)cc(Cl)c2)n1Cc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ba5fc1f5031f4ccfbaf80778181116c0 | CC(=O)OCc1nc(C(C)C)c(Sc2cc(Cl)cc(Cl)c2)n1Cc1ccncc1>>CC(C)c1nc(CO)n(Cc2ccncc2)c1Sc1cc(Cl)cc(Cl)c1 | C(C)(=O)OCC=1N(C(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl)CC1=CC=NC=C1.[OH-].[Na+]>>OCC=1N(C(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl)CC1=CC=NC=C1 | CC(=O)[O:8][CH2:7][c:6]1[n:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:17]([S:18][c:19]2[cH:20][c:21]([Cl:22])[cH:23][c:24]([Cl:25])[cH:26]2)[n:9]1[CH2:10][c:11]1[cH:12][cH:13][n:14][cH:15][cH:16]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([CH2:7][OH:8])[n:9]([CH2:10][c:11]2[cH:12][cH:13][n:14][cH:15][cH:16]2)[c:17]1[S:18][c:19]1[... | CC(=O)OCc1nc(C(C)C)c(Sc2cc(Cl)cc(Cl)c2)n1Cc1ccncc1 | CC(C)c1nc(CO)n(Cc2ccncc2)c1Sc1cc(Cl)cc(Cl)c1 | null | null | C(C)O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(Sc2cncn2Cc2ccncc2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[c:3](:[#7;a:4]):[#7;a:5]>>[#7;a:4]:[c:3](-[C:2]-[OH;D1;+0:1]):[#7;a:5] | 98.6 | [{"value": 96.9, "product": "OCC=1N(C(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl)CC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.6, "product": "OCC=1N(C(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl)CC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a suspension of the compound (11) (0.35 g, 0.77 mmol) obtained in Example 7 in ethanol (3.5 ml) was added 1N aqueous sodium hydroxide (0.82 ml) under ice-cooling. The reaction mixture was stirred for 30 minutes, concentrated under reduced pressure and extracted with ethyl acetate. The extract was washed with water a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1c[nH]cn1.c1ccncc1.c1ccccc1 | HO- | C(C)O | null | 0.5 | CC(=O)OCc1nc(C(C)C)c(Sc2cc(Cl)cc(Cl)c2)n1Cc1ccncc1>C(C)O>CC(C)c1nc(CO)n(Cc2ccncc2)c1Sc1cc(Cl)cc(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3456253717b045689467d4c971aaa76f | CC(C)c1cn(Cc2ccncc2)c(COC(N)=O)n1.ClSc1cc(Cl)cc(Cl)c1>>CC(C)c1nc(COC(N)=O)n(Cc2ccncc2)c1Sc1cc(Cl)cc(Cl)c1 | C(O)([O-])=O.[Na+].C(N)(=O)OCC=1N(C=C(N1)C(C)C)CC1=CC=NC=C1.ClC=1C=C(C=C(C1)Cl)SCl.C(C)N(CC)CC.ClC=1C=C(C=C(C1)Cl)SCl>>C(N)(=O)OCC=1N(C(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl)CC1=CC=NC=C1 | [CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([CH2:7][O:8][C:9]([NH2:10])=[O:11])[n:12]([CH2:13][c:14]2[cH:15][cH:16][n:17][cH:18][cH:19]2)[cH:20]1.Cl[S:21][c:22]1[cH:23][c:24]([Cl:25])[cH:26][c:27]([Cl:28])[cH:29]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([CH2:7][O:8][C:9]([NH2:10])=[O:11])[n:12]([CH2:13][c:14]2[cH:15][cH:16]... | CC(C)c1cn(Cc2ccncc2)c(COC(N)=O)n1.ClSc1cc(Cl)cc(Cl)c1 | CC(C)c1nc(COC(N)=O)n(Cc2ccncc2)c1Sc1cc(Cl)cc(Cl)c1 | null | null | CN(C=O)C.C1(=CC=CC=C1)C.O.CO.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 690eacd6c22fa21bb9792e4a2d7611543d6c69bb14eb007ea9f8411f0786da2b | 1d56361848b170d7aeb1292e5d4a0c5a5f2486eaf968085176af0d58840010a8 | c1ccc(Sc2cncn2Cc2ccncc2)cc1 | Cl-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7;a:6]1:[cH;D2;+0:7]:[c:8](-[C:9]):[#7;a:10]:[c:11]:1-[C:12]>>[C:5]-[#7;a:6]1:[c:11](-[C:12]):[#7;a:10]:[c:8](-[C:9]):[c;H0;D3;+0:7]:1-[S;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | 153.9 | [{"value": 61.0, "product": "C(N)(=O)OCC=1N(C(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl)CC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 153.9, "product": "C(N)(=O)OCC=1N(C(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl)CC1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | 30 | MINUTE | The compound (13) (250 mg, 0.91 mmol) was dissolved in N,N-dimethylformamide (4 ml). The solution was cooled down to −30° C. under nitrogen atmosphere. To the solution were added, alternately each four time, a solution of the compound (3) (77 mg, 0.36 mmol) in toluene (150 mg) and a solution of triethylamine (36 mg, 0.... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Monosulfide | c1cnc[nH]1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccncc1.c1ccccc1 | HCl | CN(C=O)C.C1(=CC=CC=C1)C.O.CO.C(C)(=O)OCC | -30 | 0.5 | CC(C)c1cn(Cc2ccncc2)c(COC(N)=O)n1.ClSc1cc(Cl)cc(Cl)c1>CN(C=O)C.C1(=CC=CC=C1)C.O.CO.C(C)(=O)OCC>CC(C)c1nc(COC(N)=O)n(Cc2ccncc2)c1Sc1cc(Cl)cc(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4caad36be5ac4269aa3917d91c05067e | ClCc1ccccc1.OCC=CCO>>C(=CCOCc1ccccc1)COCc1ccccc1 | [OH-].[Na+].C(C=CCO)O.C(C1=CC=CC=C1)Cl>>C(C1=CC=CC=C1)OCC=CCOCC1=CC=CC=C1 | Cl[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[CH2:1]([CH:2]=[CH:19][CH2:20][OH:13])[OH:4]>>[CH:1](=[CH:2][CH2:3][O:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[CH2:12][O:13][CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | ClCc1ccccc1.OCC=CCO | C(=CCOCc1ccccc1)COCc1ccccc1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | null | Aromatic Heterocycle Formation | OtherReaction | eb74edcf58adb84059c03bc4d1e253bf21a74ad5bb1e1948aadff5f21860c442 | a4b4d7b12f0799370a26ff3e508596a3c9f4a7de60d25daf0b68212107bd39ae | C(=CCOCc1ccccc1)COCc1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[CH2;D2;+0:6]-[CH;D2;+0:7]=[CH;D2;+0:8]-[CH2;D2;+0:9]-[OH;D1;+0:10]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[C:11]-[CH;D2;+0:8]=[CH;D2;+0:9]-[C:12]-[O;H0;D2;+0:5]-[C:13]-[c:14]1:[c:15]:[c:16]:[c:17]:[cH;D2;+0:7]:[cH;D2;+0:6]:1):[c:4] | 114.5 | [{"value": 114.5, "product": "C(C1=CC=CC=C1)OCC=CCOCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 2 | HOUR | To 48% aqueous sodium hydroxide (127.8 g) was added tetra-n-butylammonium bromide (3.3 g, 10 mmol). The mixture was heated to 60° C. To the mixture was added 2-butene-1,4-diol (17) (30.0 g, 340 mmol), to which was added dropwise benzyl chloride (94.8 g, 743 mmol) at 80±15° C. The mixture was stirred at the same tempera... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol.Primary alcohol | Ether.Ether | null | c1ccccc1 | c1ccccc1.c1ccccc1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | 60 | 2 | ClCc1ccccc1.OCC=CCO>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC>C(=CCOCc1ccccc1)COCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dee3bbe8fbf245858780f3dd89a7ddd2 | O=S(Cl)Cl.OCc1ccncc1>>Cl.ClCc1ccncc1 | OCC1=CC=NC=C1.S(=O)(Cl)Cl>>Cl.ClCC1=CC=NC=C1 | O=S([Cl:1])[Cl:2].O[CH2:3][c:4]1[cH:5][cH:6][n:7][cH:8][cH:9]1>>[ClH:1].[Cl:2][CH2:3][c:4]1[cH:5][cH:6][n:7][cH:8][cH:9]1 | O=S(Cl)Cl.OCc1ccncc1 | Cl.ClCc1ccncc1 | null | null | C(C)#N | Functional Group Interconversion | Alcohol to chloride_SOCl2 | bb752b9027dc4488ba075e5955118a819f80cabd751a7497b67c2eeb1db6b071 | cbf41c7cf9fe6b47a243b1674d74ed5bf46a151f7f3a71d206e23176e158facf | c1ccncc1 | O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.O=S(-[Cl;H0;D1;+0:8])-[Cl;H0;D1;+0:9]>>[Cl;H0;D1;+0:9]-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[ClH;D0;+0:8] | null | [] | null | null | 1 | HOUR | 4-Hydroxymethylpyridine (20) (54.4 g, 0.50 mol) was dissolved in acetonitrile 202 ml. The solution was added dropwise to a mixture of thionyl chloride (65.3 g, 0.55 mol) and acetonitrile (109 ml) under 50° C. The mixture was stirred at the same temperature for 1 hour, then cooled to room temperature to yield a slurry (... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Primary halide | null | null | c1ccncc1 | Other | C(C)#N | null | 1 | O=S(Cl)Cl.OCc1ccncc1>C(C)#N>Cl.ClCc1ccncc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b9dca31d80aa4786984f28cacece28d0 | CC(C)c1nc(COCc2ccccc2)n(Cc2ccncc2)c1Sc1cc(Cl)cc(Cl)c1>>CC(C)c1nc(CO)n(Cc2ccncc2)c1Sc1cc(Cl)cc(Cl)c1 | C(C)(C)OC(C)C.O.C(C1=CC=CC=C1)OCC=1N(C(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl)CC1=CC=NC=C1.Cl>>OCC=1N(C(=C(N1)C(C)C)SC1=CC(=CC(=C1)Cl)Cl)CC1=CC=NC=C1 | c1ccc(C[O:8][CH2:7][c:6]2[n:5][c:4]([CH:2]([CH3:1])[CH3:3])[c:17]([S:18][c:19]3[cH:20][c:21]([Cl:22])[cH:23][c:24]([Cl:25])[cH:26]3)[n:9]2[CH2:10][c:11]2[cH:12][cH:13][n:14][cH:15][cH:16]2)cc1>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]([CH2:7][OH:8])[n:9]([CH2:10][c:11]2[cH:12][cH:13][n:14][cH:15][cH:16]2)[c:17]1[S:18][c:... | CC(C)c1nc(COCc2ccccc2)n(Cc2ccncc2)c1Sc1cc(Cl)cc(Cl)c1 | CC(C)c1nc(CO)n(Cc2ccncc2)c1Sc1cc(Cl)cc(Cl)c1 | null | null | C1(=CC=CC=C1)C | Deprotection | Hydroxyl benzyl deprotection | c8a6fd2e05b2d36256c76b73aaf4118f20eb14abce1c0289b554265e30b218aa | 29a81fd08d26edc3da6d72c4958026f5af2119326dc1b4714ee5be1c41835609 | c1ccc(Sc2cncn2Cc2ccncc2)cc1 | [#7;a:1]:[c:2](-[C:3]-[O;H0;D2;+0:4]-C-c1:c:c:c:c:c:1):[#7;a:5]>>[#7;a:1]:[c:2](-[C:3]-[OH;D1;+0:4]):[#7;a:5] | null | [] | 90 | CELSIUS | 30 | MINUTE | To the compound (6) was added concentrated aqueous hydrochloric acid (50 ml). The mixture was heated at 90° C. for 2 hours and then cooled down. To the mixture were added water (50 ml) and toluene (20 ml). The aqueous layer was separated and neutralized by 30% aqueous sodium hydroxide. The compound (12) was extracted w... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol | c1ccccc1 | null | c1c[nH]cn1.c1ccncc1.c1ccccc1 | Other | C1(=CC=CC=C1)C | 90 | 0.5 | CC(C)c1nc(COCc2ccccc2)n(Cc2ccncc2)c1Sc1cc(Cl)cc(Cl)c1>C1(=CC=CC=C1)C>CC(C)c1nc(CO)n(Cc2ccncc2)c1Sc1cc(Cl)cc(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7db99835b713471dac9c78ee60d5003c | CCSC#N.NCc1ccccc1>>CCSC(=N)NCc1ccccc1 | C(C1=CC=CC=C1)N.C(C)SC#N.FC(S(=O)(=O)O[Si](C)(C)C)(F)F.[OH-].[Na+]>>C(C1=CC=CC=C1)NC(SCC)=N | [CH3:1][CH2:2][S:3][C:4]#[N:5].[NH2:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][CH2:2][S:3][C:4](=[NH:5])[NH:6][CH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | CCSC#N.NCc1ccccc1 | CCSC(=N)NCc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b89240ebb74ff81b2004e1c951aac404d121f696ab0c217d52c710976a223031 | d604976d565d2569a4f319cd13be3585eaa574c89dc6fe3078e332d84f0f1b6a | c1ccccc1 | [C:1]-[#16:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C:1]-[#16:2]-[C;H0;D3;+0:3](=[NH;D1;+0:4])-[NH;D2;+0:5]-[C:6]-[c:7] | 100 | [{"value": 100.0, "product": "C(C1=CC=CC=C1)NC(SCC)=N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | Benzylamine (13.8 mg) was dissolved in ethyl thiocyanate (50 μl). To this solution, trimethylsilyl trifluoromethanesulfonate (25.7 μl) was added dropwise at room temperature. After continued stirring for 1 day at room temperature, 2N aqueous sodium hydroxide was added to the solution, which was then extracted with ethy... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Secondary amine.Monosulfide | null | null | c1ccccc1 | null | null | null | 24 | CCSC#N.NCc1ccccc1>>CCSC(=N)NCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d1a5376db894c5fa10737f03e2c124c | Cc1ccc(S(=O)(=O)Cl)cc1.OCC(CO)(CO)CO>>Cc1ccc(S(=O)(=O)OCC(COS(=O)(=O)c2ccc(C)cc2)(COS(=O)(=O)c2ccc(C)cc2)COS(=O)(=O)c2ccc(C)cc2)cc1 | OCC(CO)(CO)CO.C1(=CC=C(C=C1)S(=O)(=O)Cl)C.Cl>>S(=O)(=O)(C1=CC=C(C)C=C1)OCC(COS(=O)(=O)C1=CC=C(C)C=C1)(COS(=O)(=O)C1=CC=C(C)C=C1)COS(=O)(=O)C1=CC=C(C)C=C1 | Cl[S:6]([c:5]1[cH:4][cH:3][c:20]([CH3:21])[cH:22][cH:48]1)(=[O:7])=[O:8].[CH2:1]([C:11]([CH2:18][OH:9])([CH2:34][OH:16])[CH2:49][OH:15])[OH:13]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][C:11]([CH2:12][O:13][S:14](=[O:15])(=[O:16])[c:17]2[cH:18][cH:19][c:20]([CH3:21])[cH:22][cH:23]2)([CH2:24][O:... | Cc1ccc(S(=O)(=O)Cl)cc1.OCC(CO)(CO)CO | Cc1ccc(S(=O)(=O)OCC(COS(=O)(=O)c2ccc(C)cc2)(COS(=O)(=O)c2ccc(C)cc2)COS(=O)(=O)c2ccc(C)cc2)cc1 | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | f4de4312e19105a37f37e06c864c6cfcf3be99025e9df975048f97a603c0ad3b | 904cf759b476fc174facec1884c678310b9f9efc014d7ec6a5e3e7917df32e8d | O=S(=O)(OCC(COS(=O)(=O)c1ccccc1)(COS(=O)(=O)c1ccccc1)COS(=O)(=O)c1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]1:[c:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[C;D1;H3:8]):[cH;D2;+0:9]:[cH;D2;+0:10]:1.[OH;D1;+0:11]-[CH2;D2;+0:12]-[C;H0;D4;+0:13](-[CH2;D2;+0:14]-[OH;D1;+0:15])(-[CH2;D2;+0:16]-[OH;D1;+0:17])-[CH2;D2;+0:18]-[OH;D1;+0:19]>>[#8:20]-[C:21]-[C;H0;D4;+0:13](-[C:22]-[O;H0;D2;+0:15... | 91 | [{"value": 91.0, "product": "S(=O)(=O)(C1=CC=C(C)C=C1)OCC(COS(=O)(=O)C1=CC=C(C)C=C1)(COS(=O)(=O)C1=CC=C(C)C=C1)COS(=O)(=O)C1=CC=C(C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.7, "product": "S(=O)(=O)(C1=CC=C(C)C=C1)OCC(COS(=O)(=O)C1=CC=C(C)C=C1)(COS(=O)(=O)C1=CC=C(C)C=C1)COS(=O)(=O)C1=CC=C(C)C... | null | null | 48 | HOUR | A mixture of pentaerythritol (27.20 grams, 199.8 mmol; obtained from Aldrich Chemical Co., Milwaukee, Wis.) and p-toluenesulfonyl chloride (171.0 grams, 897.0 mmol; obtained from Aldrich Chemical Co., Milwaukee, Wis.) in dry pyridine (300 milliliters; obtained from Anachemia) was stirred for 48 hours under nitrogen gas... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Primary alcohol.Primary alcohol.Primary alcohol.Sulfonyl halide | Tosylate.Tosylate.Tosylate.Tosylate | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | N1=CC=CC=C1 | null | 48 | Cc1ccc(S(=O)(=O)Cl)cc1.OCC(CO)(CO)CO>N1=CC=CC=C1>Cc1ccc(S(=O)(=O)OCC(COS(=O)(=O)c2ccc(C)cc2)(COS(=O)(=O)c2ccc(C)cc2)COS(=O)(=O)c2ccc(C)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1a593854508344ba9e6124d621ab3ac1 | O=[N+]([O-])c1ccc(OCC(COc2ccc([N+](=O)[O-])cc2)(COc2ccc([N+](=O)[O-])cc2)COc2ccc([N+](=O)[O-])cc2)cc1>>Nc1ccc(OCC(COc2ccc(N)cc2)(COc2ccc(N)cc2)COc2ccc(N)cc2)cc1 | [N+](=O)([O-])C1=CC=C(OCC(COC2=CC=C(C=C2)[N+](=O)[O-])(COC2=CC=C(C=C2)[N+](=O)[O-])COC2=CC=C(C=C2)[N+](=O)[O-])C=C1.[H][H]>>NC1=CC=C(OCC(COC2=CC=C(C=C2)N)(COC2=CC=C(C=C2)N)COC2=CC=C(C=C2)N)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][C:8]([CH2:9][O:10][c:11]2[cH:12][cH:13][c:14]([N+:15](=O)[O-])[cH:16][cH:17]2)([CH2:18][O:19][c:20]2[cH:21][cH:22][c:23]([N+:24](=O)[O-])[cH:25][cH:26]2)[CH2:27][O:28][c:29]2[cH:30][cH:31][c:32]([N+:33](=O)[O-])[cH:34][cH:35]2)[cH:36][cH:37]1>>[NH2:1][c:2]1[cH:3][cH:4]... | O=[N+]([O-])c1ccc(OCC(COc2ccc([N+](=O)[O-])cc2)(COc2ccc([N+](=O)[O-])cc2)COc2ccc([N+](=O)[O-])cc2)cc1 | Nc1ccc(OCC(COc2ccc(N)cc2)(COc2ccc(N)cc2)COc2ccc(N)cc2)cc1 | null | [Pd] | O1CCCC1 | Reduction | OtherReaction | d3c86ea6125f7c78a17e8ed8168d2f2012b8262d0a2be4f04cb7da17a111de15 | 6430ee6840ee8476e512674f404f6998bef2482b43937012d44e105a8f417e7d | c1ccc(OCC(COc2ccccc2)(COc2ccccc2)COc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4].O=[N+;H0;D3:5](-[O-])-[c:6](:[c:7]):[c:8].O=[N+;H0;D3:9](-[O-])-[c:10](:[c:11]):[c:12].O=[N+;H0;D3:13](-[O-])-[c:14](:[c:15]):[c:16]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12].[NH2;D1;+0:13]-[c:14](:[c:15]):[c:16] | 90 | [{"value": 90.0, "product": "NC1=CC=C(OCC(COC2=CC=C(C=C2)N)(COC2=CC=C(C=C2)N)COC2=CC=C(C=C2)N)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1,3-bis(4-nitrophenoxy)-2,2-bis [(4-nitrophenoxy)methyl]propane (15.43 grams, 24.87 mmol; prepared as described in Part B of this Example) and Pd/C 10% (1.58 grams, obtained from Aldrich Chemical Co.) was stirred for 70 hours in tetrahydrofuran (400 milliliters) under 180 pounds per square inch of hydrogen... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group.Nitro group.Nitro group | Primary amine.Primary amine.Primary amine.Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | [Pd].O1CCCC1 | null | null | O=[N+]([O-])c1ccc(OCC(COc2ccc([N+](=O)[O-])cc2)(COc2ccc([N+](=O)[O-])cc2)COc2ccc([N+](=O)[O-])cc2)cc1>[Pd].O1CCCC1>Nc1ccc(OCC(COc2ccc(N)cc2)(COc2ccc(N)cc2)COc2ccc(N)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9aac2e7889ec4119bd355f1aa6f385e9 | C1CCOC1.Clc1nc(Cl)nc(Cl)n1.Nc1ccc(OCC(COc2ccc(N)cc2)(COc2ccc(N)cc2)COc2ccc(N)cc2)cc1>>Clc1nc(Cl)nc(Nc2ccc(OCC(COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)(COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)cc2)n1 | C(=O)([O-])[O-].[Na+].[Na+].NC1=CC=C(OCC(COC2=CC=C(C=C2)N)(COC2=CC=C(C=C2)N)COC2=CC=C(C=C2)N)C=C1.O1CCCC1.N1=C(Cl)N=C(Cl)N=C1Cl>>ClC1=NC(=NC(=N1)Cl)NC1=CC=C(OCC(COC2=CC=C(C=C2)NC2=NC(=NC(=N2)Cl)Cl)(COC2=CC=C(C=C2)NC2=NC(=NC(=N2)Cl)Cl)COC2=CC=C(C=C2)NC2=NC(=NC(=N2)Cl)Cl)C=C1 | O1[CH2:38][CH2:21][CH2:42][CH2:40]1.[Cl:1][c:23]1[n:24][c:25]([Cl:26])[n:47][c:28]([Cl:29])[n:30]1.[c:2]1([NH2:69])[cH:37][cH:36][c:35]([O:34][CH2:33][C:15]([CH2:14][O:13][c:12]2[cH:11][cH:10][c:9]([NH2:8])[cH:68][cH:67]2)([CH2:16][O:17][c:18]2[cH:19][cH:20][c:7]([NH2:6])[cH:31][cH:32]2)[CH2:50][O:51][c:52]2[cH:53][cH:... | C1CCOC1.Clc1nc(Cl)nc(Cl)n1.Nc1ccc(OCC(COc2ccc(N)cc2)(COc2ccc(N)cc2)COc2ccc(N)cc2)cc1 | Clc1nc(Cl)nc(Nc2ccc(OCC(COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)(COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)cc2)n1 | null | null | CC(=O)C.O | Aromatic Heterocycle Formation | OtherReaction | cff80d086ce5b7855dad8d29e2e8b24465715777c2cfe856757bd2b4639edf68 | 895befa65f562215d98191e8d7ecbc06247e4c9531280d3dda0bca044a2f8f96 | c1ncnc(Nc2ccc(OCC(COc3ccc(Nc4ncncn4)cc3)(COc3ccc(Nc4ncncn4)cc3)COc3ccc(Nc4ncncn4)cc3)cc2)n1 | O1-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-1.[Cl;D1;H0:5]-[c;H0;D3;+0:6]1:[#7;a:7]:[c;H0;D3;+0:8](-[Cl;H0;D1;+0:9]):[#7;a:10]:[c;H0;D3;+0:11](-[Cl;D1;H0:12]):[n;H0;D2;+0:13]:1.[NH2;D1;+0:14]-[c;H0;D3;+0:15]1:[cH;D2;+0:16]:[c:17]:[c:18]:[c:19]:[cH;D2;+0:20]:1.[NH2;D1;+0:21]-[c;H0;D3;+0:22]1:[cH;D2;+0:23]... | 84 | [{"value": 84.0, "product": "ClC1=NC(=NC(=N1)Cl)NC1=CC=C(OCC(COC2=CC=C(C=C2)NC2=NC(=NC(=N2)Cl)Cl)(COC2=CC=C(C=C2)NC2=NC(=NC(=N2)Cl)Cl)COC2=CC=C(C=C2)NC2=NC(=NC(=N2)Cl)Cl)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 1 | HOUR | A solution of 1,3-bis(4-aminophenoxy)-2,2-bis[(4-aminophenoxy)methyl]propane (5.00 grams, 10.0 mmol; prepared as described in Part C of this Example) in 120 milliliters of a mixture of dry acetone and tetrahydrofuran (1:1 (v/v)) was added dropwise to a solution of cyanuric chloride (7.75 grams, 42.0 mmol; obtained from... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Ether.Primary amine.Primary amine.Primary amine.Primary amine | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Secondary amine.Secondary amine.Secondary amine.Secondary amine | C1CCOC1.c1ncncn1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ncncn1.c1ccccc1.c1ncncn1.c1ccccc1.c1ncncn1.c1ccccc1.c1ncncn1 | c1ncncn1.c1ccccc1.c1ccccc1.c1ncncn1.c1ccccc1.c1ncncn1.c1ccccc1.c1ncncn1 | HO- | CC(=O)C.O | -10 | 1 | C1CCOC1.Clc1nc(Cl)nc(Cl)n1.Nc1ccc(OCC(COc2ccc(N)cc2)(COc2ccc(N)cc2)COc2ccc(N)cc2)cc1>CC(=O)C.O>Clc1nc(Cl)nc(Nc2ccc(OCC(COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)(COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)cc2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9d76751d333c489db5273cd46d72fe74 | CCCCCCCCN.CO.Clc1nc(Cl)nc(Nc2ccc(OCC(COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)(COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)cc2)n1>>CCCCCCCCNc1nc(NCCCCCCCC)nc(Nc2ccc(OCC(COc3ccc(Nc4nc(NCCCCCCCC)nc(NCCCCCCCC)n4)cc3)(COc3ccc(Nc4nc(NCCCCCCCC)nc(NCCCCCCCC)n4)cc3)COc3ccc(Nc4nc(NCCCCCCCC)nc(NCCCCCCCC)n4)cc3)cc2)n1 | ClC1=NC(=NC(=N1)Cl)NC1=CC=C(OCC(COC2=CC=C(C=C2)NC2=NC(=NC(=N2)Cl)Cl)(COC2=CC=C(C=C2)NC2=NC(=NC(=N2)Cl)Cl)COC2=CC=C(C=C2)NC2=NC(=NC(=N2)Cl)Cl)C=C1.C(CCCCCCC)N.[OH-].[Na+].CO>>C(CCCCCCC)NC1=NC(=NC(=N1)NCCCCCCCC)NC1=CC=C(OCC(COC2=CC=C(C=C2)NC2=NC(=NC(=N2)NCCCCCCCC)NCCCCCCCC)(COC2=CC=C(C=C2)NC2=NC(=NC(=N2)NCCCCCCCC)NCCCCCC... | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH2:9].O[CH3:50].Cl[c:10]1[n:11][c:14]([NH:13][c:70]2[cH:69][cH:68][c:67]([O:66][CH2:65][C:31]([CH2:30][O:29][c:28]3[cH:27][cH:26][c:25]([NH:24][c:23]4[n:22][c:12](Cl)[n:53][c:58](Cl)[n:133]4)[cH:132][cH:131]3)([CH2:32][O:33][c:34]3[cH:35][cH:36][c:37]([NH:38][c:... | CCCCCCCCN.CO.Clc1nc(Cl)nc(Nc2ccc(OCC(COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)(COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)cc2)n1 | CCCCCCCCNc1nc(NCCCCCCCC)nc(Nc2ccc(OCC(COc3ccc(Nc4nc(NCCCCCCCC)nc(NCCCCCCCC)n4)cc3)(COc3ccc(Nc4nc(NCCCCCCCC)nc(NCCCCCCCC)n4)cc3)COc3ccc(Nc4nc(NCCCCCCCC)nc(NCCCCCCCC)n4)cc3)cc2)n1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | fa9a81d1f1a0f034e61ea7532a759afafa9e42574bc58dd5d0eba3011b0a4b12 | 3af6a3039657df43ef356a2459cb03d3eeb0246defa7f7258ee7bb3e787320ee | c1ncnc(Nc2ccc(OCC(COc3ccc(Nc4ncncn4)cc3)(COc3ccc(Nc4ncncn4)cc3)COc3ccc(Nc4ncncn4)cc3)cc2)n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7:4]):[#7;a:5]:[c;H0;D3;+0:6](-Cl):[#7;a:7]:1.Cl-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10](-[#7:11]):[#7;a:12]:[c;H0;D3;+0:13](-Cl):[#7;a:14]:1.Cl-[c;H0;D3;+0:15]1:[#7;a:16]:[c:17](-[#7:18]):[n;H0;D2;+0:19]:[c;H0;D3;+0:20](-Cl):[n;H0;D2;+0:21]:1.Cl-[c;H0;D3;+0:22]1:[n;H0;D2;+0:23]:[c;H0;D3;+0... | 69 | [{"value": 69.0, "product": "C(CCCCCCC)NC1=NC(=NC(=N1)NCCCCCCCC)NC1=CC=C(OCC(COC2=CC=C(C=C2)NC2=NC(=NC(=N2)NCCCCCCCC)NCCCCCCCC)(COC2=CC=C(C=C2)NC2=NC(=NC(=N2)NCCCCCCCC)NCCCCCCCC)COC2=CC=C(C=C2)NC2=NC(=NC(=N2)NCCCCCCCC)NCCCCCCCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1,3-bis(4-[N-(2,4-dichloro-1,3,5-triazin-6-yl)amino]phenoxy)-2,2-bis[(4-[N-(2,4-dichloro-1,3,5-triazin-6-yl)amino]phenoxy)methyl]propane (3.88 grams, 3.55 mmol; prepared as described in Part D of this Example) and octylamine (11.7 milliliters, 71.0 mmol; obtained from Aldrich Chemical Co.) in dioxane (30 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Primary amine.Secondary amine.Methanol | Secondary amine.Secondary amine.Secondary amine.Secondary amine.Secondary amine.Secondary amine.Secondary amine.Secondary amine.Secondary amine | c1ncncn1.c1ccccc1.c1ncncn1.c1ncncn1.c1ncncn1 | c1ncncn1.c1ncncn1.c1ccccc1.c1ncncn1.c1ncncn1 | c1ncncn1.c1ccccc1.c1ccccc1.c1ncncn1.c1ccccc1.c1ncncn1.c1ccccc1.c1ncncn1 | null | O1CCOCC1 | null | null | CCCCCCCCN.CO.Clc1nc(Cl)nc(Nc2ccc(OCC(COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)(COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)COc3ccc(Nc4nc(Cl)nc(Cl)n4)cc3)cc2)n1>O1CCOCC1>CCCCCCCCNc1nc(NCCCCCCCC)nc(Nc2ccc(OCC(COc3ccc(Nc4nc(NCCCCCCCC)nc(NCCCCCCCC)n4)cc3)(COc3ccc(Nc4nc(NCCCCCCCC)nc(NCCCCCCCC)n4)cc3)COc3ccc(Nc4nc(NCCCCCCCC)nc(NCCCCCCCC)n4)cc3)cc2)n... |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a7f7ae6390344917803d662834d38ff3 | O=[N+]([O-])c1ccc(OCCCCCOc2ccc([N+](=O)[O-])cc2)cc1>>Nc1ccc(OCCCCCOc2ccc(N)cc2)cc1 | [N+](=O)([O-])C1=CC=C(OCCCCCOC2=CC=C(C=C2)[N+](=O)[O-])C=C1.[H][H]>>NC1=CC=C(OCCCCCOC2=CC=C(C=C2)N)C=C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][c:16]([N+:17](=O)[O-])[cH:18][cH:19]2)[cH:20][cH:21]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][c:13]2[cH:14][cH:15][c:16]([NH2:17])[cH:18][cH:19]2)[cH:20][cH:21]1 | O=[N+]([O-])c1ccc(OCCCCCOc2ccc([N+](=O)[O-])cc2)cc1 | Nc1ccc(OCCCCCOc2ccc(N)cc2)cc1 | null | [Pd] | O1CCCC1 | Reduction | OtherReaction | 6748a51a25102225412593c5a930e43f5a8904a80803177de025a6f83c59d65e | a303b0dfb15cc6bade463acf71681cf3ba7580b599dfa4d28d8caac83d08cd17 | c1ccc(OCCCCCOc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4].O=[N+;H0;D3:5](-[O-])-[c:6](:[c:7]):[c:8]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8] | 90 | [{"value": 90.0, "product": "NC1=CC=C(OCCCCCOC2=CC=C(C=C2)N)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1,5-bis(4-nitrophenoxy)pentane (32.7 grams, 94.4 mmol; prepared as described in Part A of this Example) and Pd/C 10% (1.00 gram, obtained from Aldrich Chemical Co.) was stirred for 20 hours in tetrahydrofuran (400 milliliters) under 200 pounds per square inch of hydrogen gas. The mixture was then filtered ... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group | Primary amine.Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | [Pd].O1CCCC1 | null | null | O=[N+]([O-])c1ccc(OCCCCCOc2ccc([N+](=O)[O-])cc2)cc1>[Pd].O1CCCC1>Nc1ccc(OCCCCCOc2ccc(N)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9f1ef43dc69b44dd936cbaff8a14f96f | CCCCCCCCN.Clc1nc(Cl)nc(Cl)n1.Nc1ccc(OCCCCCOc2ccc(N)cc2)cc1>>CCCCCCCCNc1nc(NCCCCCCCC)nc(Nc2ccc(OCCCCCOc3ccc(Nc4nc(NCCCCCCCC)nc(NCCCCCCCC)n4)cc3)cc2)n1 | O.N1=C(Cl)N=C(Cl)N=C1Cl.NC1=CC=C(OCCCCCOC2=CC=C(C=C2)N)C=C1.C(CCCCCCC)N>>C(CCCCCCC)NC1=NC(=NC(=N1)NCCCCCCCC)NC1=CC=C(OCCCCCOC2=CC=C(C=C2)NC2=NC(=NC(=N2)NCCCCCCCC)NCCCCCCCC)C=C1 | [NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].Cl[c:1]1[n:9][c:5](Cl)[n:55][c:60](Cl)[n:53]1.[NH2:24][c:25]1[cH:26][cH:27][c:28]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][c:36]2[cH:37][cH:38][c:39]([NH2:40])[cH:65][cH:66]2)[cH:67][cH:68]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][... | CCCCCCCCN.Clc1nc(Cl)nc(Cl)n1.Nc1ccc(OCCCCCOc2ccc(N)cc2)cc1 | CCCCCCCCNc1nc(NCCCCCCCC)nc(Nc2ccc(OCCCCCOc3ccc(Nc4nc(NCCCCCCCC)nc(NCCCCCCCC)n4)cc3)cc2)n1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 9f2009b33b5bf6b16f62e7c4ded8b8dc30a2535e454fdf6694374e2df04c0cc0 | 53e1e38d99f2c9a3ecccd79f5225291699b0f5688394924ed960d26269b42465 | c1ncnc(Nc2ccc(OCCCCCOc3ccc(Nc4ncncn4)cc3)cc2)n1 | Cl-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-Cl):[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-Cl):[n;H0;D2;+0:6]:1.[C:7]-[C:8]-[NH2;D1;+0:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13].[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[#7:18]-[c:19]1:[#7;a:20]:[c:21](-[NH;D2;+0:14]-[c:15](:[c:16]):[c:17]):[#7;a:22]:[c:23](-[NH;D2;+0:4]-[C:24]-[... | 45.2 | [{"value": 45.0, "product": "C(CCCCCCC)NC1=NC(=NC(=N1)NCCCCCCCC)NC1=CC=C(OCCCCCOC2=CC=C(C=C2)NC2=NC(=NC(=N2)NCCCCCCCC)NCCCCCCCC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.2, "product": "C(CCCCCCC)NC1=NC(=NC(=N1)NCCCCCCCC)NC1=CC=C(OCCCCCOC2=CC=C(C=C2)NC2=NC(=NC(=N2)NCCCCCCCC)NCCCCCCCC)C=C1", "d... | null | null | null | null | A solution of cyanuric chloride (6.44 grams, 34.9 mmol; obtained from Aldrich Chemical Co.) in dry tetrahydrofuran (50 milliliters) was added dropwise to a solution of 1,5-bis(4-aminophenoxy)pentane (5.00 grams, 17.46 mmol; prepared as described in Part B of Example VIII) in dry tetrahydrofuran (100 milliliters) at −78... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Primary amine.Primary amine.Primary amine | Secondary amine.Secondary amine.Secondary amine.Secondary amine.Secondary amine.Secondary amine | c1ncncn1 | c1ncncn1.c1ncncn1 | c1ncncn1.c1ccccc1.c1ccccc1.c1ncncn1 | null | O1CCCC1 | null | null | CCCCCCCCN.Clc1nc(Cl)nc(Cl)n1.Nc1ccc(OCCCCCOc2ccc(N)cc2)cc1>O1CCCC1>CCCCCCCCNc1nc(NCCCCCCCC)nc(Nc2ccc(OCCCCCOc3ccc(Nc4nc(NCCCCCCCC)nc(NCCCCCCCC)n4)cc3)cc2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-15b09eaac7d0451581148c6eef1c9bd2 | Clc1nc(Cl)nc(Cl)n1.Nc1ccc(OCOc2ccc(N)cc2)cc1>>Clc1nc(Cl)nc(N(c2ccc(OCOc3ccc(N(c4nc(Cl)nc(Cl)n4)c4nc(Cl)nc(Cl)n4)cc3)cc2)c2nc(Cl)nc(Cl)n2)n1 | [H-].[Na+].BrCBr.N1=C(Cl)N=C(Cl)N=C1Cl.NC1=CC=C(OCOC2=CC=C(C=C2)N)C=C1>>ClC1=NC(=NC(=N1)Cl)N(C1=NC(=NC(=N1)Cl)Cl)C1=CC=C(OCOC2=CC=C(C=C2)N(C2=NC(=NC(=N2)Cl)Cl)C2=NC(=NC(=N2)Cl)Cl)C=C1 | [Cl:1][c:7]1[n:6][c:4]([Cl:5])[n:3][c:46]([Cl:47])[n:48]1.[NH2:8][c:9]1[cH:10][cH:11][c:12]([O:13][CH2:14][O:15][c:16]2[cH:17][cH:18][c:19]([NH2:20])[cH:37][cH:38]2)[cH:39][cH:40]1>>[Cl:1][c:2]1[n:3][c:4]([Cl:5])[n:6][c:7]([N:8]([c:9]2[cH:10][cH:11][c:12]([O:13][CH2:14][O:15][c:16]3[cH:17][cH:18][c:19]([N:20]([c:21]4[n... | Clc1nc(Cl)nc(Cl)n1.Nc1ccc(OCOc2ccc(N)cc2)cc1 | Clc1nc(Cl)nc(N(c2ccc(OCOc3ccc(N(c4nc(Cl)nc(Cl)n4)c4nc(Cl)nc(Cl)n4)cc3)cc2)c2nc(Cl)nc(Cl)n2)n1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 2cc450f5809a68c87116943ce147824699c5f7a135c0fa7361d2aac917d8984d | cd5cd49c2917ab72f5e08f657b75d343c09671282e69b988dccde42b8399e766 | c1ncnc(N(c2ccc(OCOc3ccc(N(c4ncncn4)c4ncncn4)cc3)cc2)c2ncncn2)n1 | [Cl;D1;H0:1]-[c;H0;D3;+0:2]1:[n;H0;D2;+0:3]:[c:4](-[Cl;D1;H0:5]):[#7;a:6]:[c;H0;D3;+0:7](-[Cl;H0;D1;+0:8]):[n;H0;D2;+0:9]:1.[NH2;D1;+0:10]-[c:11](:[c:12]):[c:13].[NH2;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[#7;a:18]:[c:19](-[N;H0;D3;+0:10](-[c:11](:[c:12]):[c:13])-[c:20](:[#7;a:21]):[#7;a:22]):[#7;a:23].[Cl;D1;H0:1]-[c;H0;D... | 16 | [{"value": 16.0, "product": "ClC1=NC(=NC(=N1)Cl)N(C1=NC(=NC(=N1)Cl)Cl)C1=CC=C(OCOC2=CC=C(C=C2)N(C2=NC(=NC(=N2)Cl)Cl)C2=NC(=NC(=N2)Cl)Cl)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 10 | MINUTE | Cyanuric chloride (11.473 grams, 62.2 mmol) in dry tetrahydrofuran (50 milliliters) was added to a solution of 1,1-bis(4-aminophenoxy)methane (3.58 grams, 15.55 mmol; prepared as described in Part B of Example VIII except that 1,1-dibromomethane was used instead of 1,5-dibromopentane) in dry tetrahydrofuran (175 millil... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine.Primary amine | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Tertiary amine.Tertiary amine | c1ncncn1 | c1ncncn1.c1ncncn1.c1ncncn1.c1ncncn1 | c1ncncn1.c1ccccc1.c1ccccc1.c1ncncn1.c1ncncn1.c1ncncn1 | Other | O1CCCC1 | 60 | 0.166667 | Clc1nc(Cl)nc(Cl)n1.Nc1ccc(OCOc2ccc(N)cc2)cc1>O1CCCC1>Clc1nc(Cl)nc(N(c2ccc(OCOc3ccc(N(c4nc(Cl)nc(Cl)n4)c4nc(Cl)nc(Cl)n4)cc3)cc2)c2nc(Cl)nc(Cl)n2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9a91687510384f2a99c8906dc00af77d | O=C(CCl)NNc1c(Cl)cc(C(F)(F)F)cc1Cl.O=P(Cl)(Cl)Cl>>FC(F)(F)c1cc(Cl)c(NN=C(Cl)CCl)c(Cl)c1 | P(=O)(Cl)(Cl)Cl.ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NNC(CCl)=O>>ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NN=C(CCl)Cl | O=[C:12]([NH:11][NH:10][c:9]1[c:7]([Cl:8])[cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:18][c:16]1[Cl:17])[CH2:14][Cl:15].O=P(Cl)(Cl)[Cl:13]>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][c:7]([Cl:8])[c:9]([NH:10][N:11]=[C:12]([Cl:13])[CH2:14][Cl:15])[c:16]([Cl:17])[cH:18]1 | O=C(CCl)NNc1c(Cl)cc(C(F)(F)F)cc1Cl.O=P(Cl)(Cl)Cl | FC(F)(F)c1cc(Cl)c(NN=C(Cl)CCl)c(Cl)c1 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | d2adb5249b835cbd5e29a1d008f8890d7d63064f04d3c086cb23bbf52e5d2c0e | 592d52b78ec2e6116b853767baf214dbded882d69fad734c4ec7064b66a98864 | c1ccccc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[C;H0;D3;+0:2](-[C:3]-[Cl;D1;H0:4])-[NH;D2;+0:5]-[#7:6]-[c:7]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[N;H0;D2;+0:5]-[#7:6]-[c:7] | 90 | [{"value": 90.0, "product": "ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NN=C(CCl)Cl", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | Phosphoryl chloride (500 microlitres, 1.7 equivalents) was added in one portion to a stirred solution of N′-(2,6-dichloro-4-trifluoromethylphenyl)-chloroacetohydrazide (1.0 g, 3.11 mmol) in toluene (20 ml) and heated at 70° C. under an argon atmosphere for 20 hours. The cooled mixture was evaporated and the residue ext... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine | Hydrazone.Alkenyl halide | null | null | c1ccccc1 | HCl | C1(=CC=CC=C1)C | 70 | null | O=C(CCl)NNc1c(Cl)cc(C(F)(F)F)cc1Cl.O=P(Cl)(Cl)Cl>C1(=CC=CC=C1)C>FC(F)(F)c1cc(Cl)c(NN=C(Cl)CCl)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dfa9e18eb14e412c912226bdf971231a | NNc1c(Cl)cc(C(F)(F)F)cc1Cl.O=C(Cl)CCl>>O=C(CCl)NNc1c(Cl)cc(C(F)(F)F)cc1Cl | ClCC(=O)Cl.ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NN.[OH-].[Na+]>>ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NNC(CCl)=O | [NH2:5][NH:6][c:7]1[c:8]([Cl:9])[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][c:17]1[Cl:18].Cl[C:2](=[O:1])[CH2:3][Cl:4]>>[O:1]=[C:2]([CH2:3][Cl:4])[NH:5][NH:6][c:7]1[c:8]([Cl:9])[cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][c:17]1[Cl:18] | NNc1c(Cl)cc(C(F)(F)F)cc1Cl.O=C(Cl)CCl | O=C(CCl)NNc1c(Cl)cc(C(F)(F)F)cc1Cl | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 76e474c9dcce40e7c35c8f78d834149480d3c5d1f85bb22ed583a932a8f908b5 | 63b8330ebf088c16fa42481d4df221c4a2a7081161aafbc66cd44502eb8a31d9 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[Cl;D1;H0:4].[NH2;D1;+0:5]-[#7:6]-[c:7]>>[Cl;D1;H0:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[#7:6]-[c:7] | 91 | [{"value": 91.0, "product": "ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NNC(CCl)=O", "details": "PERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 8.5 | HOUR | A solution of chloroacetyl chloride (2.3 ml, 1.08 equivalents) in anhydrous dichloromethane (30 ml) was added during 30 minutes to a stirred solution of 2,6-dichloro-4-trifluoromethylphenylhydrazine (6.1 g, 24.89 mmol) in anhydrous dichloromethane (60 ml) maintaining between 5 and 12° C. under an argon atmosphere. The ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Hydrazine | Acylhydrazine | null | null | c1ccccc1 | HCl | ClCCl | 20 | 8.5 | NNc1c(Cl)cc(C(F)(F)F)cc1Cl.O=C(Cl)CCl>ClCCl>O=C(CCl)NNc1c(Cl)cc(C(F)(F)F)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd9e3a31161d42c9b3f9a0536f7ed37e | CCCCCCCCSCc1ccc(CSCCCCCCCC)cc1.Cl>>CCCCCCCCSCc1ccc(CCl)cc1 | C1CC[S+](C1)CC2=CC=C(C=C2)C[S+]3CCCC3.[Cl-].[Cl-].CC(C)([O-])C.[Na+].C(CCCCCCC)S.Cl.C(CCCCCCC)SCC1=CC=C(C=C1)CSCCCCCCCC>>C(CCCCCCC)SCC1=CC=C(CCl)C=C1 | CCCCCCCCS[CH2:15][c:14]1[cH:13][cH:12][c:11]([CH2:10][S:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[cH:18][cH:17]1.[ClH:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([CH2:15][Cl:16])[cH:17][cH:18]1 | CCCCCCCCSCc1ccc(CSCCCCCCCC)cc1.Cl | CCCCCCCCSCc1ccc(CCl)cc1 | null | null | CO | Miscellaneous | OtherReaction | 568fcece0b0b1a58f2cd9ab66423b5a75f1a58b07c92e8e5c6e6f72a6aa2e9ca | da371f332928e9795b7e5953d710718b264f7bc7f0ee900390ed5b651ce0c486 | c1ccccc1 | C-C-C-C-C-C-C-C-S-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[ClH;D0;+0:5]>>[Cl;H0;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | 1.83 g (19 mmol) of sodium t-butoxide and 2.78 g (19 mmol) of octanethiol were stirred into 40 g of methanol at room temperature. After 30 minutes, the clear solution was added in one portion to 6.68 g (19 mmol) of the p-xylylenebis(tetrahydrothiophenium chloride) obtained in accordance with Example 1, in 100 g of meth... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Primary halide | null | null | c1ccccc1 | Other | CO | null | 0.5 | CCCCCCCCSCc1ccc(CSCCCCCCCC)cc1.Cl>CO>CCCCCCCCSCc1ccc(CCl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1dafe2e64013446290804c2d6d9417a2 | CCCCCCCCS.ClCc1ccc(CCl)cc1>>CCCCCCCCSCc1ccc(CCl)cc1 | Cl.C1(=CC=C(C=C1)CCl)CCl.CC(C)([O-])C.[Na+].C(CCCCCCC)S>>C(CCCCCCC)SCC1=CC=C(CCl)C=C1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][SH:9].Cl[CH2:10][c:11]1[cH:12][cH:13][c:14]([CH2:15][Cl:16])[cH:17][cH:18]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][S:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([CH2:15][Cl:16])[cH:17][cH:18]1 | CCCCCCCCS.ClCc1ccc(CCl)cc1 | CCCCCCCCSCc1ccc(CCl)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 77cd742b5ba20df0e225494f6e5f3d958ee82ce9a1b16fd99a2d9f8350b4fdc8 | b05f7dda7dad719ae1868a84c33eeaf5bf649036fc64173cf4774a5eb4d70181 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[SH;D1;+0:7]>>[C:5]-[C:6]-[S;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | 1.83 g (19 mmol) of sodium t-butoxide and 2.78 g (19 mmol) of octanethiol were stirred into 40 g of methanol at room temperature. After 30 minutes, the clear solution was added in one portion to 3.33 g (19 mmol) of p-xylylene dichloride in 100 g of methanol. After one hour, the mixture was neutralized using 1N hydrochl... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aliphatic thiol | Monosulfide | null | null | c1ccccc1 | HCl | CO | null | 0.5 | CCCCCCCCS.ClCc1ccc(CCl)cc1>CO>CCCCCCCCSCc1ccc(CCl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3cf88f8f01ae4eda9158f1af5217637a | CC(C)(C)[O][K].CN(C)C=O.O=Cc1ccccc1>>O=C(O)c1ccccc1.OCc1ccccc1 | C(F)(F)F.C(C)(C)(C)O[K].CN(C)C=O.C(C1=CC=CC=C1)=O>>C(C1=CC=CC=C1)O.C(C1=CC=CC=C1)(=O)O | C[C:12]([O:3][K])([CH3:5])[CH3:6].N([CH3:7])([CH3:9])[CH:11]=[O:10].[O:1]=[CH:2][c:4]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1.[OH:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | CC(C)(C)[O][K].CN(C)C=O.O=Cc1ccccc1 | O=C(O)c1ccccc1.OCc1ccccc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 6690e4e46cb273f3dd0902365fc32ec3d8d80bc5ff3346d76e18d40d75b3b265 | b7bb234b9c619b11dbbcc65b9eefdcb531ac3e7d9b4f675ac84213955a0dd700 | c1ccccc1.c1ccccc1 | C-[C;H0;D4;+0:1](-[CH3;D1;+0:2])(-[CH3;D1;+0:3])-[O;H0;D2;+0:4]-[K].[CH3;D1;+0:5]-N(-[CH3;D1;+0:6])-[CH;D2;+0:7]=[O;H0;D1;+0:8].[O;D1;H0:9]=[CH;D2;+0:10]-[c;H0;D3;+0:11]1:[cH;D2;+0:12]:[c:13]:[c:14]:[c:15]:[cH;D2;+0:16]:1>>[O;D1;H0:9]=[C;H0;D3;+0:10](-[OH;D1;+0:4])-[c;H0;D3;+0:11]1:[cH;D2;+0:2]:[cH;D2;+0:3]:[cH;D2;+0:5... | null | [] | null | null | null | null | Shono and co-workers found that when they used CF3H/tBuOK/DMF to react with benzaldehyde at −50° C., benzyl alcohol and benzoic acid were formed by the competing Cannizzaro reaction (Shono, T.; Ishifume, M.; Okada, T.; Kashimura, S. J. Org. Chem. 1991, 56, 2). As mentioned above, the product of the present method is su... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Tertiary amide | Carboxylic acid.Primary alcohol | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Other | null | null | null | CC(C)(C)[O][K].CN(C)C=O.O=Cc1ccccc1>>O=C(O)c1ccccc1.OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a6ef70945a064cf8aa5b23fae875897f | Ic1ccccc1.O=C(c1ccccc1)C(F)(F)F>>FC(F)(F)c1ccccc1 | C1(=CC=CC=C1)S(=O)(=O)C(F)(F)F.C(C)(C)(C)O[K].C1(=CC=CC=C1)S(=O)(=O)C(F)(F)F.C(C)(C)(C)O[K].C(C1=CC=CC=C1)(=O)OC.IC1=CC=CC=C1.FC(C(=O)C1=CC=CC=C1)(F)F>>FC(C1=CC=CC=C1)(F)F | I[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.O=C(c1ccccc1)[C:2]([F:1])([F:3])[F:4]>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1 | Ic1ccccc1.O=C(c1ccccc1)C(F)(F)F | FC(F)(F)c1ccccc1 | null | [Cu](I)I | null | C-C Coupling | OtherReaction | 882d585dfeaf9af3b459fab96e21e086649257ed61b28fae77af423d24744b9b | 69252060bd8bb16a3d129f54075340a581c58d00d601fbeb8c019de79dd14833 | c1ccccc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O=C(-c1:c:c:c:c:c:1)-[C;H0;D4;+0:6](-[F;D1;H0:7])(-[F;D1;H0:8])-[F;D1;H0:9]>>[F;D1;H0:7]-[C;H0;D4;+0:6](-[F;D1;H0:8])(-[F;D1;H0:9])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 26 | [{"value": 26.0, "product": "FC(C1=CC=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The trifluoromethyl phenyl sulfone/tBuOK trifluoromethylation method can also be applied to other systems. For instance, methyl benzoate can be trifluoromethylated to generate 2,2,2-trifluoroacetophenone in 30% yield at about −50° C. to about −20° C. CF3Cu can be in situ generated with trifluoromethyl phenyl sulfone/tB... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Ketone | Trifluoro group | c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccccc1 | HI | [Cu](I)I | null | null | Ic1ccccc1.O=C(c1ccccc1)C(F)(F)F>[Cu](I)I>FC(F)(F)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-22e1ed36935945f98fd23107fff48bed | Cc1ccc(C(=O)c2ccccc2)cc1.O=S(=O)(c1ccccc1)C(F)(F)F>>Cc1ccc(C(O)(c2ccccc2)C(F)(F)F)cc1 | C(C)(C)(C)O[K].FC(F)(F)S(=O)(=O)C1=CC=CC=C1.CC1=CC=C(C(=O)C2=CC=CC=C2)C=C1>>CC1=CC=C(C=C1)C(O)(C(F)(F)F)C1=CC=CC=C1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:18][cH:19]1.O=S(=O)(c1ccccc1)[C:14]([F:15])([F:16])[F:17]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]([OH:7])([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]1 | Cc1ccc(C(=O)c2ccccc2)cc1.O=S(=O)(c1ccccc1)C(F)(F)F | Cc1ccc(C(O)(c2ccccc2)C(F)(F)F)cc1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 9b85fd893e7ce6d701a18b179912ee1fc2a0868057f61b782352848f1105e885 | 8464e050491d156a3e05a451fd07dd53c913decfec1ae3f76af99cea7aa5ed13 | c1ccc(Cc2ccccc2)cc1 | O=S(=O)(-c1:c:c:c:c:c:1)-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;D1;H0:3])-[F;D1;H0:4].[O;H0;D1;+0:5]=[C;H0;D3;+0:6](-[c:7](:[c:8]):[c:9])-[c:10](:[c:11]):[c:12]>>[F;D1;H0:2]-[C;H0;D4;+0:1](-[F;D1;H0:3])(-[F;D1;H0:4])-[C;H0;D4;+0:6](-[OH;D1;+0:5])(-[c:7](:[c:8]):[c:9])-[c:10](:[c:11]):[c:12] | 85 | [{"value": 85.0, "product": "CC1=CC=C(C=C1)C(O)(C(F)(F)F)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.5, "product": "CC1=CC=C(C=C1)C(O)(C(F)(F)F)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -50 | CELSIUS | 1 | HOUR | Into a dry Schlenk flask under an argon atmosphere, was added 7 mL DMF solution of phenyl trifluoromethyl sulfone (1a, 420 mg, 2 mmol) and 4-methylbenzophenone (196 mg, 1 mmol) at −50° C., was added 3 mL DMF solution of tBuOK (280 mg, 2.5 mmol). The reaction flask was then sealed and the reaction mixture was then stirr... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Ketone.Sulfone | Trifluoro group.Tertiary alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | -50 | 1 | Cc1ccc(C(=O)c2ccccc2)cc1.O=S(=O)(c1ccccc1)C(F)(F)F>CN(C)C=O>Cc1ccc(C(O)(c2ccccc2)C(F)(F)F)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ad5b508534d646d4979319e3b7844155 | O=Cc1ccc(Cl)cc1.O=S(=O)(c1ccccc1)C(F)(F)C(O)c1ccccc1>>OC(c1ccccc1)C(F)(F)C(O)c1ccc(Cl)cc1 | CC(C)(C)[O-].[K+].C1(=CC=CC=C1)S(=O)(=O)C(F)(F)C(O)C1=CC=CC=C1.ClC1=CC=C(C=O)C=C1>>FC(C(O)C1=CC=CC=C1)(C(O)C1=CC=C(C=C1)Cl)F | [CH:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1.O=S(=O)(c1ccccc1)[C:9]([CH:2]([OH:1])[c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)([F:10])[F:11]>>[OH:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][cH:8]1)[C:9]([F:10])([F:11])[CH:12]([OH:13])[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1 | O=Cc1ccc(Cl)cc1.O=S(=O)(c1ccccc1)C(F)(F)C(O)c1ccccc1 | OC(c1ccccc1)C(F)(F)C(O)c1ccc(Cl)cc1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 72fb58a24c0d949a3e1d602fd3b29dfc264c10dc1667bfc2fcfd6e7c73fd0d00 | a9a25c21f03dbd8629e27691f96f07ad6293a6d718eaca9f112fe3026430690f | c1ccc(CCCc2ccccc2)cc1 | O=S(=O)(-c1:c:c:c:c:c:1)-[C;H0;D4;+0:1](-[F;D1;H0:2])(-[F;D1;H0:3])-[C:4](-[O;D1;H1:5])-[c:6].[O;H0;D1;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[F;D1;H0:2]-[C;H0;D4;+0:1](-[F;D1;H0:3])(-[C:4](-[O;D1;H1:5])-[c:6])-[CH;D3;+0:8](-[OH;D1;+0:7])-[c:9](:[c:10]):[c:11] | 76 | [{"value": 76.0, "product": "FC(C(O)C1=CC=CC=C1)(C(O)C1=CC=C(C=C1)Cl)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Into the mixture of PhSO2CF2CH(OH)Ph (120 mg, 0.4 mmol) and 4-chlorobenzaldehyde (113 mg, 0.8 mmol) in DMF (3 mL) at −50° C., was added t-BuOK (90 mg, 0.8 mmol) in 2 mL DMF. The reaction mixture was stirred at −50° C. to RT overnight. The reaction was then quenched with cold NaCl aqueous solution, followed by extractio... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Aldehyde.Sulfone | Tertiary halide.Tertiary halide.Secondary alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | null | 8 | O=Cc1ccc(Cl)cc1.O=S(=O)(c1ccccc1)C(F)(F)C(O)c1ccccc1>CN(C)C=O>OC(c1ccccc1)C(F)(F)C(O)c1ccc(Cl)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-22db996d591f4d78a18857d82c7798ef | COC(=O)[C@@H](C)O.Nc1ccc(F)c(F)c1F>>COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | FC1=C(N)C=CC(=C1F)F.C([C@H](O)C)(=O)OC.N1=C(C=CC=C1C)C.Cl.FC(S(=O)(=O)O)(F)F>>FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F | O[C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH3:6].[NH2:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16] | COC(=O)[C@@H](C)O.Nc1ccc(F)c(F)c1F | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | null | null | ClCCl | Heteroatom Alkylation and Arylation | Reductive amination with alcohol | 36e22efc5c6318558e24d6b03014b042e8843045ca88b79012548acde5bec2e7 | 5dd73d2983238aca5aad5303ecb23b666bd0b69f1b23e89b064b81beff99b7b2 | c1ccccc1 | O-[C@H;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C@H;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 90 | [{"value": 90.0, "product": "FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.9, "product": "FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Under ice-cooling, methyl D-lactate (8.5 g) and 2,6-lutidine (11.4 g) were dissolved in dichloromethane (100 ml). After dropping anhydrous trifluoromethanesulfonic acid (25.4 g), the mixture was heated to room temperature and stirred for 30 minutes. Then it was cooled to 0° C. again and a solution (30 ml) of 2,3,4-trif... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary alcohol.Primary amine | Ester.Secondary amine | null | null | c1ccccc1 | HO- | ClCCl | null | 0.5 | COC(=O)[C@@H](C)O.Nc1ccc(F)c(F)c1F>ClCCl>COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d9b0bffd894b426d850fcbbf6660c959 | COC(=O)[C@@H](C)OS(C)(=O)=O.Nc1ccc(F)c(F)c1F>>COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | FC1=C(N)C=CC(=C1F)F.C([O-])([O-])=O.[K+].[K+].CS(=O)(=O)O[C@@H](C(=O)OC)C>>FC1=C(N[C@H](C(=O)OC)C)C=CC(=C1F)F | CS(=O)(=O)O[C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH3:6].[NH2:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16] | COC(=O)[C@@H](C)OS(C)(=O)=O.Nc1ccc(F)c(F)c1F | COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F | null | [Cl-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC | null | Heteroatom Alkylation and Arylation | Alkylation of amines | 6b6c28579602aff04a935e88c83680e78439493fb7de3c74a967610cf233f7cc | f84282e972229159aa1b10d3e270f49c44676514c64dc43730c647e4568a04ee | c1ccccc1 | C-S(=O)(=O)-O-[C@H;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C@H;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | In accordance with the process of Example 2, a condensation reaction was performed by using 2,3,4-trifluoroaniline (100 mg), potassium carbonate (188 mg), methyl (2R)-2-[(methanesulfonyl)oxy]propionate (78 mg) and tetrahexylammonium chloride (40 mg) to give the title compound as an oily substance. As the result of the ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Ester.Primary amine | Ester.Secondary amine | null | null | c1ccccc1 | MsOH.HO- | [Cl-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC | null | null | COC(=O)[C@@H](C)OS(C)(=O)=O.Nc1ccc(F)c(F)c1F>[Cl-].C(CCCCC)[N+](CCCCCC)(CCCCCC)CCCCCC>COC(=O)[C@H](C)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-df2cd1af74594089ac13ed08c39f07ae | COC(=O)C(C)=O.O=[N+]([O-])c1ccc(F)c(F)c1F>>COC(=O)C(C)Nc1ccc(F)c(F)c1F | [H][H].FC1=C(C=CC(=C1F)F)[N+](=O)[O-].C(C(=O)C)(=O)OC.S(=O)(=O)([O-])[O-].[Mg+2]>>FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F | O=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH3:6].O=[N+:7]([O-])[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16] | COC(=O)C(C)=O.O=[N+]([O-])c1ccc(F)c(F)c1F | COC(=O)C(C)Nc1ccc(F)c(F)c1F | null | [Pd] | CO | Functional Group Interconversion | OtherReaction | afc456d3801dde7d01420f0407f1359d2151a7caf861685c22d21aa320014574 | 7a6ac26784750edae2ec5255c2f631040bbac914a02bb7a5f5351faf04e687c3 | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].O=[N+;H0;D3:7](-[O-])-[c:8](:[c:9]):[c:10]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 97.4 | [{"value": 97.4, "product": "FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 2,3, 4-Trifluoronitrobenzene (100 g) and methyl pyruvate (57.6 g) were dissolved in methanol (1000 ml). After adding 5% Pd—C (20.0 g) and anhydrous magnesium sulfate (90 g), the mixture was stirred at room temperature in a hydrogen atmosphere for 16 hours. Then the liquid reaction mixture was filtered through celite to... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitro group | Ester.Secondary amine | null | null | c1ccccc1 | Other | [Pd].CO | null | 2 | COC(=O)C(C)=O.O=[N+]([O-])c1ccc(F)c(F)c1F>[Pd].CO>COC(=O)C(C)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3aa39437285a4e61ad16bed02546d92a | COC(=O)C(C)=O.Nc1ccc(F)c(F)c1F>>COC(=O)C(C)Nc1ccc(F)c(F)c1F | [H][H].FC1=C(N)C=CC(=C1F)F.C(C(=O)C)(=O)OC.S(=O)(=O)([O-])[O-].[Mg+2]>>FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F | O=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH3:6].[NH2:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[NH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[c:15]1[F:16] | COC(=O)C(C)=O.Nc1ccc(F)c(F)c1F | COC(=O)C(C)Nc1ccc(F)c(F)c1F | null | [Pd] | CO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 9ead86cf12aa15d642a54ce216bcf061aaad412b712c6fec7fa57e8d47412e01 | a0caba33875db4cbb9ed690a5345ca767b0ef35f758b719cf286d2968627181f | c1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C;D1;H3:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[C;D1;H3:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 95.3 | [{"value": 95.3, "product": "FC1=C(NC(C(=O)OC)C)C=CC(=C1F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2,3,4-Trifluoroaniline (2.94 g) and methyl pyruvate (2.04 g) were dissolved in methanol (30 ml). After adding 5% Pd—C (2.0 g) and anhydrous magnesium sulfate (2.65 g), the mixture was stirred at 50° C. in a hydrogen atmosphere for 16 hours. After filtering off Pd—C and magnesium sulfate, the obtained filtrate was conce... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Ester.Secondary amine | null | null | c1ccccc1 | Other | [Pd].CO | null | null | COC(=O)C(C)=O.Nc1ccc(F)c(F)c1F>[Pd].CO>COC(=O)C(C)Nc1ccc(F)c(F)c1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ef41386ffd2e4542a863081859790979 | CCO.COC(=O)C(C)=O.O=[N+]([O-])c1ccc(F)c(F)c1F>>CCOC(=O)C(C)Nc1ccc(F)c(F)c1F | [H][H].FC1=C(C=CC(=C1F)F)[N+](=O)[O-].C(C(=O)C)(=O)OC.C(C)O.S(=O)(=O)([O-])[O-].[Mg+2]>>FC1=C(NC(C(=O)OCC)C)C=CC(=C1F)F | [CH3:1][CH2:2][OH:3].CO[C:4](=[O:5])[C:6](=O)[CH3:7].O=[N+:8]([O-])[c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([F:13])[c:14]([F:15])[c:16]1[F:17] | CCO.COC(=O)C(C)=O.O=[N+]([O-])c1ccc(F)c(F)c1F | CCOC(=O)C(C)Nc1ccc(F)c(F)c1F | null | [Pd] | C(C)(=O)OCC.CCCCCC | Functional Group Interconversion | OtherReaction | 7425bb8de5ee3209424461b8f6c9211e65fea80d66dae3199de8319e57a60bd4 | 6b9611246291786824d8abe62e17aa511fac3cb83ebce9729570ad77ef3bc09c | c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=O)-[C;D1;H3:4].O=[N+;H0;D3:5](-[O-])-[c:6](:[c:7]):[c:8].[C;D1;H3:9]-[C:10]-[OH;D1;+0:11]>>[C;D1;H3:9]-[C:10]-[O;H0;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-[C;D1;H3:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | 2,3,4-Trifluoronitrobenzene (3.54 g) and methyl pyruvate (2.32 g) were dissolved in ethanol (30 ml). After adding 5% Pd—C (2.0 g) and anhydrous magnesium sulfate (2.65 g), the mixture was stirred at 50° C. in a hydrogen atmosphere for 16 hours. After filtering off Pd—C and magnesium sulfate, the obtained filtrate was c... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Nitro group.Primary alcohol | Ester.Secondary amine | null | null | c1ccccc1 | HO- | [Pd].C(C)(=O)OCC.CCCCCC | null | null | CCO.COC(=O)C(C)=O.O=[N+]([O-])c1ccc(F)c(F)c1F>[Pd].C(C)(=O)OCC.CCCCCC>CCOC(=O)C(C)Nc1ccc(F)c(F)c1F |
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