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-df24f20e04da4cf9bb28b80952681e46 | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3n2C)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3n2C)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | C(C)(=O)C1=CC=C(C(=O)O)C=C1.COC1=C(C=O)C=C(C(=C1)OC)C=1N(C2=CC=CC=C2C1)C>>COC1=C(C=C(C(=C1)OC)C=1N(C2=CC=CC=C2C1)C)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1 | [CH3:22][C:23](=[O:24])[c:25]1[cH:26][cH:27][c:28]([C:29](=[O:30])[OH:31])[cH:32][cH:33]1.O=[CH:21][c:20]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[n:17]2[CH3:18])[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:1... | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3n2C)cc1C=O | COc1cc(OC)c(-c2cc3ccccc3n2C)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cc3ccccc3[nH]2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 87 | [{"value": 87.0, "product": "COC1=C(C=C(C(=C1)OC)C=1N(C2=CC=CC=C2C1)C)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 4-acetylbenzoic acid and 2,4-dimethoxy-5-(1-methyl-1H-indol-2-yl)-benzaldehyde (Ex-116A) in a similar manner as described in Ex-3. Yellow solid, 87% yield, mp 157–160° C. 1H-NMR (DMSO-d6) δ 8.17 (d, J=8 Hz, 2H), 8.08 (d, J=15 Hz, 1H), 7.99–9.02 (m 3H), 7.83 (d, J=15 Hz, 1H)... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1cc2ccccc2[nH]1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(C(=O)O)cc1.COc1cc(OC)c(-c2cc3ccccc3n2C)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3n2C)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4008bb8a60f04f23b51dc898f7d8ac43 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2cc3ccccc3n2C)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3n2C)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N.COC1=C(C=O)C=C(C(=C1)OC)C=1N(C2=CC=CC=C2C1)C>>COC1=C(C=C(C(=C1)OC)C=1N(C2=CC=CC=C2C1)C)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N | [CH3:22][C:23](=[O:24])[c:25]1[cH:26][cH:27][c:28]([S:29]([NH2:30])(=[O:31])=[O:32])[cH:33][cH:34]1.O=[CH:21][c:20]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[n:17]2[CH3:18])[cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[c... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2cc3ccccc3n2C)cc1C=O | COc1cc(OC)c(-c2cc3ccccc3n2C)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | null | null | null | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(-c2cc3ccccc3[nH]2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 90 | [{"value": 90.0, "product": "COC1=C(C=C(C(=C1)OC)C=1N(C2=CC=CC=C2C1)C)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by condensing 4-acetyl-benzenesulfonamide (Ex-26A) and 2,4-dimethoxy-5-(1-methyl-1H-indol-2-yl)-benzaldehyde (Ex-116A) in a similar manner as described in Ex-3. Yellow solid, 90% yield, mp 148–150° C. 1H-NMR (CDCl3) δ 8.17 (d, J=16 Hz, 1H), 8.09 (d, J=9 Hz, 2H), 8.01 (d, J=9 Hz, 2H), 7.6... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1cc2ccccc2[nH]1.c1ccccc1 | HO- | null | null | null | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(-c2cc3ccccc3n2C)cc1C=O>>COc1cc(OC)c(-c2cc3ccccc3n2C)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-121190dfed7e49c9b66c38f912eb6470 | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1>>COC(=O)c1ccc(C(=O)/C=C/c2cc(-c3cc4ccccc4s3)c(OC)cc2OC)cc1 | S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC)C=CC=C2.CCN=C=NCCCN(C)C>>COC(C1=CC=C(C=C1)C(\C=C\C1=C(C=C(C(=C1)C1=CC2=C(S1)C=CC=C2)OC)OC)=O)=O | [OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])/[CH:11]=[CH:12]/[c:13]2[cH:14][c:15](-[c:16]3[cH:17][c:18]4[cH:19][cH:20][cH:21][cH:22][c:23]4[s:24]3)[c:25]([O:26][CH3:27])[cH:28][c:29]2[O:30][CH3:31])[cH:32][cH:33]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])/[CH:11]=[CH:12]/[c:13]2[cH:1... | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | COC(=O)c1ccc(C(=O)/C=C/c2cc(-c3cc4ccccc4s3)c(OC)cc2OC)cc1 | null | CN(C)C=1C=CN=CC1 | CO | Miscellaneous | Protection of carboxylic acid | 56520e0abb4535dce9a663824ca803b71c2c0dd72dfd246317d953596a987bd2 | 2ccc7a30191c2c171b49e8a0217bee87430687dd0f567141eca025a75b7e3136 | O=C(/C=C/c1cccc(-c2cc3ccccc3s2)c1)c1ccccc1 | [O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[c:4]>>[C;D1;H3:5]-[O;H0;D2;+0:3]-[C:2](=[O;D1;H0:1])-[c:4] | 34 | [{"value": 34.0, "product": "COC(C1=CC=C(C=C1)C(\\C=C\\C1=C(C=C(C(=C1)C1=CC2=C(S1)C=CC=C2)OC)OC)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by esterification of 4-[3E-(5-Benzo[b]thiophen-2-yl-2,4-dimethoxy-phenyl)-acryloyl]-benzoic acid (Ex-3) with methanol in the presence of EDCI and DMAP. Yellow solid, 34% yield, m.p. 149–151° C. 1H-NMR (300 MHz, CDCl3): 8.17 (d, 2H, J=6.7 Hz), 8.10 (d, 1H, J=15.8 Hz), 8.05 (d, 2H, J=6.7 H... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | c1ccccc1.c1ccccc1.c1ccc2sccc2c1 | Other | CN(C)C=1C=CN=CC1.CO | null | null | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1>CN(C)C=1C=CN=CC1.CO>COC(=O)c1ccc(C(=O)/C=C/c2cc(-c3cc4ccccc4s3)c(OC)cc2OC)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-102420b016204a699014c908bf046c20 | C1=COCC1.O=Cc1cccc(Br)c1>>O=Cc1cccc(C2CC=CO2)c1 | BrC=1C=CC=C(C=O)C1.O1CCC=C1.C([O-])([O-])=O.[Cs+].[Cs+]>>O1C(CC=C1)C=1C=C(C=O)C=CC1 | [CH2:8]1[CH2:9][CH:10]=[CH:11][O:12]1.Br[c:7]1[cH:6][cH:5][cH:4][c:3]([CH:2]=[O:1])[cH:13]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][c:7]([CH:8]2[CH2:9][CH:10]=[CH:11][O:12]2)[cH:13]1 | C1=COCC1.O=Cc1cccc(Br)c1 | O=Cc1cccc(C2CC=CO2)c1 | null | CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C | O.O1CCOCC1 | C-C Coupling | OtherReaction | b4051ff7812d7cf0468f49113ffe018c214c07832327c3b42ebcaca827365c2f | 3443c4588802a91da83028657a198e0d6619987ecc7555a2d5e93ba54d1cefc1 | C1=COC(c2ccccc2)C1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6]:[c:7].[#8:8]1-[C:9]=[C:10]-[C:11]-[CH2;D2;+0:12]-1>>[O;D1;H0:5]=[C:4]-[c:3]:[c:2]:[c;H0;D3;+0:1](-[CH;D3;+0:12]1-[#8:8]-[C:9]=[C:10]-[C:11]-1):[c:6]:[c:7] | 40 | [{"value": 40.0, "product": "O1C(CC=C1)C=1C=C(C=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.3, "product": "O1C(CC=C1)C=1C=C(C=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | null | null | Ex-119A: 5-Bromobenzaldehyde (0.5 g, 2.7 mmol) and 2,3-dihydrofuran (0.56 g, 8.1 mmol) were dissolved in dioxane (5.0 mL). Nitrogen was bubbled into the solution for 15 min followed by the sequential addition of cesium carbonate (0.96 g, 2.9 mmol) and bis(tri-t-butylphosphine)palladium(0) (0.014 g, 0.027 mmol). The sol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | Ether | C1=COCC1.c1ccccc1 | c1ccccc1.C1=COCC1 | c1ccccc1.C1=COCC1 | HBr | CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.O.O1CCOCC1 | 45 | null | C1=COCC1.O=Cc1cccc(Br)c1>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.O.O1CCOCC1>O=Cc1cccc(C2CC=CO2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed4268e224394520a5276dcd202bcc05 | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC)C=CC=C2.C(C)O.C(C)O.S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC)C=CC=C2.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.N(C)C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO>>CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O... | [CH3:14][O:15][c:16]1[cH:17][c:18]([O:19][CH3:20])[c:21](-[c:22]2[cH:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]3[s:30]2)[cH:31][c:32]1/[CH:33]=[CH:34]/[C:35](=[O:36])[c:37]1[cH:38][cH:39][c:40]([C:41](=[O:42])[OH:43])[cH:44][cH:45]1>>[CH3:14][O:15][c:16]1[cH:17][c:18]([O:19][CH3:20])[c:21](-[c:22]2[cH:23][c:24]3[cH:2... | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(/C=C/c1cccc(-c2cc3ccccc3s2)c1)c1ccccc1 | null | 63 | [{"value": 63.0, "product": "CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.S1C2=C(C=C1C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C(=O)O)C=C1)OC)OC)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | 4-[3E-(5-Benzo[b]thien-2-yl-2,4-dimethoxyphenyl)-acryloyl]-benzoic acid of Ex. 3 was then made into a meglumine salt by suspending the 4-[3E-(5-benzo[b]thien-2-yl-2,4-dimethoxy-phenyl)-acryloyl]-benzoic acid (4.45 g, 10 mmol) and N-methyl-D-glucamine (1.95 g, 10 mmol) in THF (100 mL). The mixture was stirred at room te... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccc2sccc2c1.c1ccccc1 | null | C1CCOC1 | null | 0.083333 | COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1>C1CCOC1>COc1cc(OC)c(-c2cc3ccccc3s2)cc1/C=C/C(=O)c1ccc(C(=O)O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6afee8efff1c471f86bb728d2c260d3f | C1=COCC1.COc1cc(OC)c(C=O)cc1Br>>COc1cc(OC)c(C2C=CCO2)cc1C=O | BrC=1C(=CC(=C(C=O)C1)OC)OC.O1CCC=C1.C([O-])([O-])=O.[Cs+].[Cs+].C([O-])([O-])=O.[Cs+].[Cs+].O1CCC=C1>>O1C(C=CC1)C=1C(=CC(=C(C=O)C1)OC)OC | [CH:9]1=[CH:10][CH2:11][CH2:12][O:13]1.Br[c:8]1[c:5]([O:6][CH3:7])[cH:4][c:3]([O:2][CH3:1])[c:15]([CH:16]=[O:17])[cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([CH:9]2[CH:10]=[CH:11][CH2:12][O:13]2)[cH:14][c:15]1[CH:16]=[O:17] | C1=COCC1.COc1cc(OC)c(C=O)cc1Br | COc1cc(OC)c(C2C=CCO2)cc1C=O | null | CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.[Pd] | O.O1CCOCC1 | C-C Coupling | OtherReaction | 413b6e05569e921eef7402c1b4571776ae22bc64b64a6ffc6f42f3ccfc1a789e | 3443c4588802a91da83028657a198e0d6619987ecc7555a2d5e93ba54d1cefc1 | C1=CC(c2ccccc2)OC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8].[#8:9]1-[C:10]-[CH2;D2;+0:11]-[CH;D2;+0:12]=[CH;D2;+0:13]-1>>[#8:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[CH;D3;+0:13]1-[#8:9]-[C:10]-[CH;D2;+0:11]=[CH;D2;+0:12]-1):[c:2]:[c:3]-[C:4]=[O;D1;H0:5] | 50 | [{"value": 50.0, "product": "O1C(C=CC1)C=1C(=CC(=C(C=O)C1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.2, "product": "O1C(C=CC1)C=1C(=CC(=C(C=O)C1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 45 | CELSIUS | null | null | Ex-121A: 5-Bromo-2,4-dimethoxybenzaldehyde (1.0 g, 4.0 mmol) and 2,3-dihydrofuran (0.85 g, 12.2 mmol) were dissolved in dioxane (10.0 mL). Nitrogen was bubbled into the solution for 15 min followed by the sequential addition of cesium carbonate (1.4 g, 4.5 mmol) and bis(tri-t-butylphosphine)palladium (0) (0.021 g, 0.04... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | Ether | C1=COCC1.c1ccccc1 | c1ccccc1.C1=CCOC1 | c1ccccc1.C1=CCOC1 | HBr | CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.[Pd].O.O1CCOCC1 | 45 | null | C1=COCC1.COc1cc(OC)c(C=O)cc1Br>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.[Pd].O.O1CCOCC1>COc1cc(OC)c(C2C=CCO2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5e15b01335cb4372a6985500921ddfea | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(C2C=CCO2)cc1C=O>>COc1cc(OC)c(C2C=CCO2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | O1C(C=CC1)C=1C(=CC(=C(C=O)C1)OC)OC.C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N.C[O-].[Li+]>>O1C(C=CC1)C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OC)OC | [CH3:17][C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([S:24]([NH2:25])(=[O:26])=[O:27])[cH:28][cH:29]1.O=[CH:16][c:15]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8]([CH:9]2[CH:10]=[CH:11][CH2:12][O:13]2)[cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([CH:9]2[CH:10]=[CH:11][CH2:12][O:13]2)[cH:14][c:15]1/[CH:... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(C2C=CCO2)cc1C=O | COc1cc(OC)c(C2C=CCO2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 | null | null | O.CN(C=O)C.CO | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cccc(C2C=CCO2)c1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 72.8 | [{"value": 70.0, "product": "O1C(C=CC1)C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.8, "product": "O1C(C=CC1)C=1C(=CC(=C(C1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 5-(2,5-Dihydro-furan-2-yl)-2,4-dimethoxy-benzaldehyde (Ex-121A, 0.10 g, 0.43 mmol) and 4-acetylbenzenesulfonamide (Ex-26A, 0.085 g, 0.43 mmol) were dissolved in a dimethylformamide-methanol solution (2.9 mL, 7:3). After complete dissolution, lithium methoxide (0.065 g, 1.7 mmol) was added and the resulting orange slurr... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.C1=CCOC1.c1ccccc1 | HO- | O.CN(C=O)C.CO | null | 4 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(OC)c(C2C=CCO2)cc1C=O>O.CN(C=O)C.CO>COc1cc(OC)c(C2C=CCO2)cc1/C=C/C(=O)c1ccc(S(N)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bf7cac834a044372bd0d04983d7dc8e9 | COc1cc(O)c(C=O)cc1-c1cccs1.Cc1cccc(Br)n1>>COc1cc(Oc2cccc(C)n2)c(C=O)cc1-c1cccs1 | [O-]C1=CC=CC=C1.C([O-])([O-])=O.[Cs+].[Cs+].OC1=C(C=O)C=C(C(=C1)OC)C=1SC=CC1.BrC1=NC(=CC=C1)C.C1(=CC=CC2=CC=CC=C12)C(=O)O.C([O-])([O-])=O.[Cs+].[Cs+]>>COC1=CC(=C(C=O)C=C1C=1SC=CC1)OC1=NC(=CC=C1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]([OH:6])[c:14]([CH:15]=[O:16])[cH:17][c:18]1-[c:19]1[cH:20][cH:21][cH:22][s:23]1.Br[c:7]1[cH:8][cH:9][cH:10][c:11]([CH3:12])[n:13]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][cH:10][c:11]([CH3:12])[n:13]2)[c:14]([CH:15]=[O:16])[cH:17][c:18]1-[c:19]1[cH:20][cH:21][cH:22][s:23]1 | COc1cc(O)c(C=O)cc1-c1cccs1.Cc1cccc(Br)n1 | COc1cc(Oc2cccc(C)n2)c(C=O)cc1-c1cccs1 | null | null | C(C)(=O)OCC.[OH-].[Na+].C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 99925b30dd2603ae575cba81b58435d015cd6b7267cf347380904f25833af5f2 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2ccc(-c3cccs3)cc2)nc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[C:7]-[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[O;D1;H0:6]=[C:7]-[c:8]:[c:9](-[O;H0;D2;+0:10]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:11] | 65.9 | [{"value": 65.0, "product": "COC1=CC(=C(C=O)C=C1C=1SC=CC1)OC1=NC(=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.9, "product": "COC1=CC(=C(C=O)C=C1C=1SC=CC1)OC1=NC(=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | Ex-122A: To a solution of 2-hydroxy-4-methoxy-5-thiophen-2-yl-benzaldehyde (0.68 g, 2.9 mmol) and 2-bromo-6-methylpyridine (0.25 g, 1.4 mmol) in toluene (1.0 mL) was added ethyl acetate (0.0063 g, 0.072 mmol, 1-naphthoic acid (0.50 g, 2.9 mmol), 5 Å molecular sieves (0.36 g), cesium carbonate (0.94 g, 2.9 mmol), and co... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccsc1 | HBr | C(C)(=O)OCC.[OH-].[Na+].C1(=CC=CC=C1)C | 110 | null | COc1cc(O)c(C=O)cc1-c1cccs1.Cc1cccc(Br)n1>C(C)(=O)OCC.[OH-].[Na+].C1(=CC=CC=C1)C>COc1cc(Oc2cccc(C)n2)c(C=O)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0a7cdf7bc4c84be6b16e9755a8d7b988 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(Oc2cccc(C)n2)c(C=O)cc1-c1cccs1>>COc1cc(Oc2cccc(C)n2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | COC1=CC(=C(C=O)C=C1C=1SC=CC1)OC1=NC(=CC=C1)C.C(C)(=O)C1=CC=C(C=C1)S(=O)(=O)N.C[O-].[Li+]>>COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OC1=NC(=CC=C1)C | [CH3:16][C:17](=[O:18])[c:19]1[cH:20][cH:21][c:22]([S:23]([NH2:24])(=[O:25])=[O:26])[cH:27][cH:28]1.O=[CH:15][c:14]1[c:5]([O:6][c:7]2[cH:8][cH:9][cH:10][c:11]([CH3:12])[n:13]2)[cH:4][c:3]([O:2][CH3:1])[c:30](-[c:31]2[cH:32][cH:33][cH:34][s:35]2)[cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][c:7]2[cH:8][cH:9][cH:10][c:11... | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(Oc2cccc(C)n2)c(C=O)cc1-c1cccs1 | COc1cc(Oc2cccc(C)n2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 | null | null | O.CN(C=O)C.CO | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1cc(-c2cccs2)ccc1Oc1ccccn1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[O;D1;H0:7]=[C:6](-[c:8])/[CH;D2;+0:5]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | 82 | [{"value": 82.0, "product": "COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OC1=NC(=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.6, "product": "COC1=CC(=C(C=C1C=1SC=CC1)/C=C/C(=O)C1=CC=C(C=C1)S(=O)(=O)N)OC1=NC(=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 4-Methoxy-2-(6-methyl-pyridin-2-yloxy)-5-thiophen-2-yl-benzaldehyde (Ex-122A, 0.20 g, 0.62 mmol) and 4-acetylbenzenesulfonamide (Ex-26A, 0.12 g, 0.62 mmol) were dissolved in a dimethylformamide-methanol solution (4.2 mL, 7:3). After complete dissolution, lithium methoxide (0.093 g, 2.5 mmol) was added and the resulting... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccncc1.c1ccccc1.c1ccsc1 | HO- | O.CN(C=O)C.CO | null | 3 | CC(=O)c1ccc(S(N)(=O)=O)cc1.COc1cc(Oc2cccc(C)n2)c(C=O)cc1-c1cccs1>O.CN(C=O)C.CO>COc1cc(Oc2cccc(C)n2)c(/C=C/C(=O)c2ccc(S(N)(=O)=O)cc2)cc1-c1cccs1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e6aaf19072de4abd8400219da961b065 | COc1ccc(C=O)c(OC)c1.ClI>>COc1cc(OC)c(C=O)cc1I | COC1=C(C=O)C=CC(=C1)OC.ICl.Cl>>IC=1C(=CC(=C(C=O)C1)OC)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([CH:9]=[O:10])[cH:11][cH:12]1.Cl[I:13]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8]([CH:9]=[O:10])[cH:11][c:12]1[I:13] | COc1ccc(C=O)c(OC)c1.ClI | COc1cc(OC)c(C=O)cc1I | null | null | CO | Functional Group Interconversion | OtherReaction | f6effe61353895b318215d8bd9b6bb1105cafbf7be8c217d748df587260b32c3 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccccc1 | Cl-[I;H0;D1;+0:1].[#8:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]-[C:8]=[O;D1;H0:9]>>[#8:2]-[c:3](:[c:4]):[c;H0;D3;+0:5](-[I;H0;D1;+0:1]):[c:6]:[c:7]-[C:8]=[O;D1;H0:9] | 87.5 | [{"value": 87.5, "product": "IC=1C(=CC(=C(C=O)C1)OC)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.1, "product": "IC=1C(=CC(=C(C=O)C1)OC)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 2,4-dimethoxy-benzaldehyde (20.0 g, 120.4 mmol) in methanol (550 mL) was added a solution of iodine monochloride (23.25 g, 144.9 mmol) in methanol (60 mL) dropwise over 20 min. The solution was allowed to stir at ambient temperature for 3 hours and then poured into a solution of hydrochloric acid (0.5 ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | CO | null | 3 | COc1ccc(C=O)c(OC)c1.ClI>CO>COc1cc(OC)c(C=O)cc1I |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b7422b77623e43858abc2bb907b837a8 | COc1cc(OC)c(C=O)cc1I.OB(O)c1cc2ccccc2s1>>COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O | [F-].[K+].IC=1C(=CC(=C(C=O)C1)OC)OC.S1C2=C(C=C1B(O)O)C=CC=C2.C(C)(C)(C)P(C(C)(C)C)C(C)(C)C.IC=1C(=CC(=C(C=O)C1)OC)OC>>S1C2=C(C=C1C=1C(=CC(=C(C=O)C1)OC)OC)C=CC=C2 | I[c:19]1[c:3]([O:2][CH3:1])[cH:4][c:5]([O:6][CH3:7])[c:8]([CH:20]=[O:21])[cH:18]1.OB(O)[c:9]1[cH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[s:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[cH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[s:17]2)[cH:18][c:19]1[CH:20]=[O:21] | COc1cc(OC)c(C=O)cc1I.OB(O)c1cc2ccccc2s1 | COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | O1CCCC1 | C-C Coupling | Suzuki coupling with boronic acids | 15493b37b8243b24918da50e88da7a22606e9a543d93422d66b895008aa4e97c | 743f778b861da0302c62360b1c4b2edc21b2c3696b81449369faeaaeab501dbc | c1ccc(-c2cc3ccccc3s2)cc1 | I-[c;H0;D3;+0:1]1:[c:2]:[c;H0;D3;+0:3](-[CH;D2;+0:4]=[O;D1;H0:5]):[c:6](-[#8:7]):[c:8]:[c:9]:1-[#8:10].O-B(-O)-[c;H0;D3;+0:11]1:[#16;a:12]:[c:13]:[c:14]:[c:15]:1>>[#8:10]-[c:9]1:[c:8]:[c:6](-[#8:7]):[c;H0;D3;+0:3](-[c;H0;D3;+0:11]2:[#16;a:12]:[c:13]:[c:14]:[c:15]:2):[c:2]:[c;H0;D3;+0:1]:1-[CH;D2;+0:4]=[O;D1;H0:5] | null | [] | 60 | CELSIUS | null | null | Ex-123A: Potassium fluoride (0.42 g, 7.2 mmol), 5-iodo-2,4-dimethoxy-benzaldehyde (Ex-123, 1.0 g, 3.42 mmol), 2-benzo[b]thiophene boronic acid (0.67 g, 3.77 mmol), degased tetrahydrofuran (10 mL), tris(dibenzylideneacetone)dipalladium (19 mg, 0.02 mmol), and tri-tert-butylphosphine (100 mg, 0.05 mmol) were sequentially... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde.Boronic acid | Aldehyde | c1ccccc1.c1ccc2sccc2c1 | c1ccccc1.c1ccc2sccc2c1 | c1ccccc1.c1ccc2sccc2c1 | HI.B | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCCC1 | 60 | null | COc1cc(OC)c(C=O)cc1I.OB(O)c1cc2ccccc2s1>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].O1CCCC1>COc1cc(OC)c(-c2cc3ccccc3s2)cc1C=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-868789ba44d24a379570d31b85128dc2 | NN.O=[N+]([O-])c1cc(C(F)(F)F)ccc1Cl>>On1nnc2ccc(C(F)(F)F)cc21 | ClC1=C(C=C(C=C1)C(F)(F)F)[N+](=O)[O-].O.NN>>ON1N=NC2=C1C=C(C=C2)C(F)(F)F | [NH2:3][NH2:4].[O-][N+:2](=[O:1])[c:14]1[c:5](Cl)[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13]1>>[OH:1][n:2]1[n:3][n:4][c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]12 | NN.O=[N+]([O-])c1cc(C(F)(F)F)ccc1Cl | On1nnc2ccc(C(F)(F)F)cc21 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 7782c5939184dde3a46439ac85e20224c3ad846fa2633d412f760cf18c068c41 | 6c13d8453d798e86c74ea5b8e76450673bfcfa8a64f81673730723d26d8a44f7 | c1ccc2[nH]nnc2c1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[N+;H0;D3:5](-[O-])=[O;H0;D1;+0:6]):[c:7].[NH2;D1;+0:8]-[NH2;D1;+0:9]>>[OH;D1;+0:6]-[n;H0;D3;+0:5]1:[n;H0;D2;+0:8]:[n;H0;D2;+0:9]:[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:1:[c:7] | 89.5 | [{"value": 89.5, "product": "ON1N=NC2=C1C=C(C=C2)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound is prepared according to the procedure described by K. Takeda [J. Org. Chem., 50, 273, (1985)]. A mixture of 4-chloro-3-nitro-α,α,α-trifluorotoluene (50.0 g, 0.22 moles) and hydrazine hydrate (33.0, 0.33 moles) in absolute ethanol (75 ml) is refluxed for 24 h. After removal of the solvent under reduc... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide.Nitro group | null | c1ccccc1 | c1ccc2nn[nH]c2c1 | c1ccc2nn[nH]c2c1 | HCl | C(C)O | null | null | NN.O=[N+]([O-])c1cc(C(F)(F)F)ccc1Cl>C(C)O>On1nnc2ccc(C(F)(F)F)cc21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ffec451764134a1db4236c62aaba0bd9 | CC(=O)CCC(=O)O.CC(C)N=C=NC(C)C>>CCN(C(C)C)C(C)C | C(CCC(=O)C)(=O)O.CC(N=C=NC(C)C)C.C(Cl)Cl>>CCN(C(C)C)C(C)C | O=C(O)CCC(=O)[CH3:1].N(C([CH3:5])[CH3:6])=[C:4]=[N:3][CH:7]([CH3:8])[CH3:9]>>[CH3:1][CH2:2][N:3]([CH:4]([CH3:5])[CH3:6])[CH:7]([CH3:8])[CH3:9] | CC(=O)CCC(=O)O.CC(C)N=C=NC(C)C | CCN(C(C)C)C(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d52d66f4d1f27d3af58f45752829cc7ce71f2866d14fa1307908438015cf7969 | 2f72a54a0c44eacd3ec84f33e577f211923309990de7cce0a6eaf1c53d41f642 | null | O-C(=O)-C-C-C(=O)-[CH3;D1;+0:1].[C;D1;H3:2]-[C:3](-[C;D1;H3:4])-[N;H0;D2;+0:5]=[C;H0;D2;+0:6]=N-C(-[CH3;D1;+0:7])-[CH3;D1;+0:8]>>[C;D1;H3:2]-[C:3](-[C;D1;H3:4])-[N;H0;D3;+0:5](-[C:9]-[CH3;D1;+0:1])-[CH;D3;+0:6](-[CH3;D1;+0:7])-[CH3;D1;+0:8] | null | [] | null | null | null | null | addition of activated levulinic acid (activated as the symmetric anhydride with 0.5 equivalents of DIC in DCM for 5-10 min)
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone | Tertiary amine | null | null | null | HO- | null | null | null | CC(=O)CCC(=O)O.CC(C)N=C=NC(C)C>>CCN(C(C)C)C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ebb811057e7d4e2089d709387e100252 | O=C(Cl)OCc1ccccc1.O=C(O)C1CCNCC1>>O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1 | C(C1=CC=CC=C1)OC(=O)Cl.C(=O)(OCC1=CC=CC=C1)N1CCC(C(=O)O)CC1.N1CCC(C(=O)O)CC1.C([O-])(O)=O.[Na+]>>C(=O)(OCC1=CC=CC=C1)N1CCC(C(=O)O)CC1 | Cl[C:8](=[O:9])[O:10][CH2:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][NH:7][CH2:18][CH2:19]1>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH2:6][N:7]([C:8](=[O:9])[O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1 | O=C(Cl)OCc1ccccc1.O=C(O)C1CCNCC1 | O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1 | null | null | O.C1(=CC=CC=C1)C | Protection | N-alkylation of secondary amines with alkyl halides | c6eb958652ca8104567d61601fc03a9cfee33fb7bb328952993831b03fec41c4 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | O=C(OCc1ccccc1)N1CCCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[C:6]-[C:5])-[C:8]-[C:9] | 86 | [{"value": 86.0, "product": "C(=O)(OCC1=CC=CC=C1)N1CCC(C(=O)O)CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.6, "product": "C(=O)(OCC1=CC=CC=C1)N1CCC(C(=O)O)CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 14 | HOUR | N-CBZ-isonipecotic acid Benzyl chloroformate (16.4 mL, 115 mmol) in toluene (50 mL) was added dropwise to a stirred solution of 12.9 g (100 mmol) of isonipecotic acid (Aldrich) and 21.0 g (250 mmol) of sodium bicarbonate in 200 mL of water. After 14 h, the mixture was extracted with ether (3×50 ml) and the ether layers... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1 | HCl | O.C1(=CC=CC=C1)C | null | 14 | O=C(Cl)OCc1ccccc1.O=C(O)C1CCNCC1>O.C1(=CC=CC=C1)C>O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-040a36dbcef644d3b7a53d23ebd88f75 | CCOC(=O)CC(=O)OCC.Cc1ccc(Br)c(F)c1>>CCOC(=O)C(C(=O)OCC)c1ccc(C)cc1F | C(CC(=O)OCC)(=O)OCC.[H-].[Na+].BrC1=C(C=C(C=C1)C)F.Cl>>FC1=C(C=CC(=C1)C)C(C(=O)OCC)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[O:9][CH2:10][CH3:11].Br[c:12]1[cH:13][cH:14][c:15]([CH3:16])[cH:17][c:18]1[F:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[c:12]1[cH:13][cH:14][c:15]([CH3:16])[cH:17][c:18]1[F:19] | CCOC(=O)CC(=O)OCC.Cc1ccc(Br)c(F)c1 | CCOC(=O)C(C(=O)OCC)c1ccc(C)cc1F | null | null | O1CCOCC1 | C-C Coupling | Hurtley reaction | 5a1171068c2a10d196160f01101b1c97354196d6923cfc455c6b686284d6c6f2 | c0fb657475d92a5e1ab643a3f03921ebe4d047c8d805f98b012a5df3f9fb1f6c | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D3;+0:11](-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6] | 59.6 | [{"value": 59.6, "product": "FC1=C(C=CC(=C1)C)C(C(=O)OCC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 10 | MINUTE | 0.49 mol of diethyl malonate was added at 60° C. inside 2 hours to a mixture of 0.51 mol of NaH and 140 ml of 1,4-dioxane. The mixture was stirred for approximately 10 min at 60° C. and then 0.05 mol of Cu(I)Br was added. After 15 min, a mixture of 0.25 mol of 4-bromo-3-fluorotoluene and 10 ml of 1,4-dioxane was added.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester.Ester | Ester.Ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | HBr | O1CCOCC1 | 60 | 0.166667 | CCOC(=O)CC(=O)OCC.Cc1ccc(Br)c(F)c1>O1CCOCC1>CCOC(=O)C(C(=O)OCC)c1ccc(C)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f4cfd8c165894839adb182360ea432e1 | CC(=O)Nc1ccc(/C=C/C(=O)O)cn1.Cc1ccc2cccc(OCc3c(Cl)ccc(N(C)C(=O)CN)c3Cl)c2n1>>CC(=O)Nc1ccc(/C=C/C(=O)NCC(=O)N(C)c2ccc(Cl)c(COc3cccc4ccc(C)nc34)c2Cl)cn1 | NCC(=O)N(C)C=1C(=C(COC=2C=CC=C3C=CC(=NC23)C)C(=CC1)Cl)Cl.C(C)(=O)NC1=CC=C(C=N1)/C=C/C(=O)O.ON1N=NC2=C1C=CC=C2.Cl.C(C)N=C=NCCCN(C)C>>C(C)(=O)NC1=CC=C(C=N1)/C=C/C(=O)NCC(=O)N(C)C=1C(=C(COC=2C=CC=C3C=CC(=NC23)C)C(=CC1)Cl)Cl | O[C:11](/[CH:10]=[CH:9]/[c:8]1[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[n:41][cH:40]1)=[O:12].[NH2:13][CH2:14][C:15](=[O:16])[N:17]([CH3:18])[c:19]1[cH:20][cH:21][c:22]([Cl:23])[c:24]([CH2:25][O:26][c:27]2[cH:28][cH:29][cH:30][c:31]3[cH:32][cH:33][c:34]([CH3:35])[n:36][c:37]23)[c:38]1[Cl:39]>>[CH3:1][C:2](=[O:3])[N... | CC(=O)Nc1ccc(/C=C/C(=O)O)cn1.Cc1ccc2cccc(OCc3c(Cl)ccc(N(C)C(=O)CN)c3Cl)c2n1 | CC(=O)Nc1ccc(/C=C/C(=O)NCC(=O)N(C)c2ccc(Cl)c(COc3cccc4ccc(C)nc34)c2Cl)cn1 | null | null | O.CN(C=O)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(/C=C/c1cccnc1)NCC(=O)Nc1cccc(COc2cccc3cccnc23)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])/[C:3]=[C:4]/[c:5](:[c:6]):[c:7]:[#7;a:8].[C;D1;H3:9]-[#7:10](-[c:11])-[C:12](=[O;D1;H0:13])-[C:14]-[NH2;D1;+0:15]>>[#7;a:8]:[c:7]:[c:5](/[C:4]=[C:3]/[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:15]-[C:14]-[C:12](=[O;D1;H0:13])-[#7:10](-[C;D1;H3:9])-[c:11]):[c:6] | 53.8 | [{"value": 53.8, "product": "C(C)(=O)NC1=CC=C(C=N1)/C=C/C(=O)NCC(=O)N(C)C=1C(=C(COC=2C=CC=C3C=CC(=NC23)C)C(=CC1)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a mixture of 8-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-2-methylquinoline (100 mg), (E)-3-(6-acetamidopyridin-3-yl)acrylic acid (56.1 mg) and N,N-dimethylformamide (2 ml) were added 1-hydroxybenzotriazole (43.4 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (56.9 mg) in a nitrogen stre... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccccc1.c1ccc2ncccc2c1 | HO- | O.CN(C=O)C | null | 2 | CC(=O)Nc1ccc(/C=C/C(=O)O)cn1.Cc1ccc2cccc(OCc3c(Cl)ccc(N(C)C(=O)CN)c3Cl)c2n1>O.CN(C=O)C>CC(=O)Nc1ccc(/C=C/C(=O)NCC(=O)N(C)c2ccc(Cl)c(COc3cccc4ccc(C)nc34)c2Cl)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c6da0580259c4980b9f5ec2af98dfe19 | O=C(CCl)CCl.c1nc[nH]n1>>O=C(Cn1cncn1)Cn1cncn1 | ClCC(=O)CCl.N1N=CN=C1>>N1(N=CN=C1)CC(CN1N=CN=C1)=O | Cl[CH2:3][C:2](=[O:1])[CH2:5]Cl.[n:4]1[nH:10][cH:11][n:12][cH:13]1>>[O:1]=[C:2]([CH2:3][n:4]1[cH:5][n:6][cH:7][n:8]1)[CH2:9][n:10]1[cH:11][n:12][cH:13][n:14]1 | O=C(CCl)CCl.c1nc[nH]n1 | O=C(Cn1cncn1)Cn1cncn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 90bae339f52889fdabd8686acc1edf342b27a03a66f2d05c7a8a9253bdeb0552 | 277d117055f0fa9c0a7b0fdec46e3e097718c606328ceb6568d2848aeec088a0 | O=C(Cn1cncn1)Cn1cncn1 | Cl-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-Cl.[#7;a:5]1:[c:6]:[nH;D2;+0:7]:[n;H0;D2;+0:8]:[cH;D2;+0:9]:1>>[O;D1;H0:3]=[C;H0;D3;+0:2](-[C:10]-[n;H0;D3;+0:7]1:[#7;a:11]:[cH;D2;+0:9]:[#7;a:5]:[c:6]:1)-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[#7;a:12]:[c:13]:[#7;a:14]:[cH;D2;+0:4]:1 | null | [] | null | null | null | null | According to the Spanish Patent Number ES 549 020 A1 1 mole of 1,3-dichloroacetone is reacted with 2 mole of 1,2,4-triazole, then the 1,3-bis(1,2,4-triazole-1-yl)-propan-2-on obtained with low yield is reacted with 2,4-difluorophenylmagnesium bromide to give fluconazole. The yield is about 45% calculated on the Grignar... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Ketone | Ketone | c1nc[nH]n1 | c1nc[nH]n1.c1nc[nH]n1 | c1nc[nH]n1.c1nc[nH]n1 | null | null | null | null | O=C(CCl)CCl.c1nc[nH]n1>>O=C(Cn1cncn1)Cn1cncn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-62a977a3af3043749e5018d7d27db422 | CO.C[Si](C)(C)OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F>>O.OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F | FC1=C(C=CC(=C1)F)C(CN1N=CN=C1)(CN1N=CN=C1)O[Si](C)(C)C.CO.Cl>>O.FC1=C(C=CC(=C1)F)C(CN1N=CN=C1)(CN1N=CN=C1)O | C[OH:1].C[Si](C)(C)[O:2][C:3]([CH2:4][n:5]1[cH:6][n:7][cH:8][n:9]1)([CH2:10][n:11]1[cH:12][n:13][cH:14][n:15]1)[c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][c:22]1[F:23]>>[OH2:1].[OH:2][C:3]([CH2:4][n:5]1[cH:6][n:7][cH:8][n:9]1)([CH2:10][n:11]1[cH:12][n:13][cH:14][n:15]1)[c:16]1[cH:17][cH:18][c:19]([F:20])[cH:21][c:22]1[F... | CO.C[Si](C)(C)OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F | O.OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F | null | null | O | Miscellaneous | OtherReaction | 357eac61f447b32e729168579f8528da7da26588dfc2d31885d5df9d98532f35 | 844fd118cb6d4293b2696a11189831ba9ccdbbec968ff2a96f22a1fed914fdaf | c1ccc(C(Cn2cncn2)Cn2cncn2)cc1 | C-[OH;D1;+0:1].C-[Si](-C)(-C)-[O;H0;D2;+0:2]-[C:3](-[C:4])(-[C:5])-[c:6]>>[C:4]-[C:3](-[C:5])(-[OH;D1;+0:2])-[c:6].[OH2;D0;+0:1] | 186.9 | [{"value": 93.5, "product": "O.FC1=C(C=CC(=C1)F)C(CN1N=CN=C1)(CN1N=CN=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 186.9, "product": "O.FC1=C(C=CC(=C1)F)C(CN1N=CN=C1)(CN1N=CN=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 7.50 g (0.02 mol) of 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazole-1-yl)-2-(trimethylsilyloxy)propane, 25 ml of methanol, 2 ml of water and 1.0 ml of concd. hydrochloric acid was stirred at 30° C. for 1 h. The reaction mixture was concentrated to a volume of 10 ml and after adding 50 ml of water the pH of ... | 10.6084/m9.figshare.5104873.v1 | null | Methanol.Silyl protective group | Tertiary alcohol | null | null | c1nc[nH]n1.c1nc[nH]n1.c1ccccc1 | Other | O | null | null | CO.C[Si](C)(C)OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F>O>O.OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b91f17c041f48b492f8978539c07591 | C[Si](C)(C)OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F>>OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F | FC1=C(C=CC(=C1)F)C(CN1N=CN=C1)(CN1N=CN=C1)O[Si](C)(C)C.CO.[OH-].[Na+]>>C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O | C[Si](C)(C)[O:1][C:2]([CH2:3][n:4]1[cH:5][n:6][cH:7][n:8]1)([CH2:9][n:10]1[cH:11][n:12][cH:13][n:14]1)[c:15]1[cH:16][cH:17][c:18]([F:19])[cH:20][c:21]1[F:22]>>[OH:1][C:2]([CH2:3][n:4]1[cH:5][n:6][cH:7][n:8]1)([CH2:9][n:10]1[cH:11][n:12][cH:13][n:14]1)[c:15]1[cH:16][cH:17][c:18]([F:19])[cH:20][c:21]1[F:22] | C[Si](C)(C)OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F | OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F | null | null | O | Deprotection | Alcohol deprotection from silyl ethers | 6d1f3bf0e00171fd9431270b3a5c35c615a5f2d97feae7c0a7b6dc8ba859d8aa | bf9cbf8f6c3a5d5e13b674dc7a2b872a6c60a00401e068847221a255cbca9558 | c1ccc(C(Cn2cncn2)Cn2cncn2)cc1 | C-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])(-[C:4])-[c:5]>>[C:3]-[C:2](-[C:4])(-[OH;D1;+0:1])-[c:5] | 87.4 | [{"value": 87.4, "product": "C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.3, "product": "C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 7.5 g (0.02 mol) of 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazole-1-yl)-2-(trimethylsilyloxy)propane, 40 ml of methanol, 3 ml of water and 0.1 g of sodium hydroxide was stirred at room temperature for 1 h. After adding 300 ml of water the solution was concentrated to a volume of 50 ml with vacuum distillat... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Tertiary alcohol | null | null | c1nc[nH]n1.c1nc[nH]n1.c1ccccc1 | Other | O | null | 1 | C[Si](C)(C)OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F>O>OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-480e5f12a0f94e4fa19353d5e0dfbe3c | C[Si](C)(C)OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F>>OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F | FC1=C(C=CC(=C1)F)C(CN1N=CN=C1)(CN1N=CN=C1)O[Si](C)(C)C.CO.[OH-].[Na+]>>C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O | C[Si](C)(C)[O:1][C:2]([CH2:3][n:4]1[cH:5][n:6][cH:7][n:8]1)([CH2:9][n:10]1[cH:11][n:12][cH:13][n:14]1)[c:15]1[cH:16][cH:17][c:18]([F:19])[cH:20][c:21]1[F:22]>>[OH:1][C:2]([CH2:3][n:4]1[cH:5][n:6][cH:7][n:8]1)([CH2:9][n:10]1[cH:11][n:12][cH:13][n:14]1)[c:15]1[cH:16][cH:17][c:18]([F:19])[cH:20][c:21]1[F:22] | C[Si](C)(C)OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F | OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F | null | null | O | Deprotection | Alcohol deprotection from silyl ethers | 6d1f3bf0e00171fd9431270b3a5c35c615a5f2d97feae7c0a7b6dc8ba859d8aa | bf9cbf8f6c3a5d5e13b674dc7a2b872a6c60a00401e068847221a255cbca9558 | c1ccc(C(Cn2cncn2)Cn2cncn2)cc1 | C-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])(-[C:4])-[c:5]>>[C:3]-[C:2](-[C:4])(-[OH;D1;+0:1])-[c:5] | 89 | [{"value": 87.4, "product": "C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.0, "product": "C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 7.5 g (0.02 mol) of 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazole-1-yl)-2-(trimethylsilyloxy)propane, 40 ml of methanol, 3 ml of water and 0.1 g of sodium hydroxide was stirred at room temperature for 1 h. After adding 300 ml of water the solution was concentrated to a volume of 50 ml with vacuum distillat... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Tertiary alcohol | null | null | c1nc[nH]n1.c1nc[nH]n1.c1ccccc1 | Other | O | null | 1 | C[Si](C)(C)OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F>O>OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4c3d7276b6f746199ab6434788921770 | CCCC(C(=O)O)=C1SC[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1>>CCCC(C(=O)O)C1SC[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1 | O=C1N([C@H]2[C@@H](N1CC1=CC=CC=C1)CSC2=C(C(=O)O)CCC)CC2=CC=CC=C2.[OH-].[Na+].[H][H]>>O=C1N([C@H]2[C@@H](N1CC1=CC=CC=C1)CSC2C(C(=O)O)CCC)CC2=CC=CC=C2 | [CH3:1][CH2:2][CH2:3][C:4]([C:5](=[O:6])[OH:7])=[C:8]1[S:9][CH2:10][C@H:11]2[C@@H:12]1[N:13]([CH2:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[C:21](=[O:22])[N:23]2[CH2:24][c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1>>[CH3:1][CH2:2][CH2:3][CH:4]([C:5](=[O:6])[OH:7])[CH:8]1[S:9][CH2:10][C@H:11]2[C@@H:12]1[N:13]([CH2:1... | CCCC(C(=O)O)=C1SC[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1 | CCCC(C(=O)O)C1SC[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1 | null | [Pd] | O | Reduction | Hydrogenation (double to single) | 56117d34fca93ce7bdb006f432bbbbc4f9d0278f718c367e0efaeae3929f8de9 | 229264280d760663074461f898bce2a68d1dd7a993ad956085f2c6522e0edd11 | O=C1N(Cc2ccccc2)[C@@H]2CSC[C@@H]2N1Cc1ccccc1 | [C:1]-[#7:2]1-[C:3]2-[C:4](-[#7:5]-[C:6]-1=[O;D1;H0:7])-[C:8]-[#16:9]-[C;H0;D3;+0:10]-2=[C;H0;D3;+0:11](-[C:12]-[C:13])-[C:14](=[O;D1;H0:15])-[O;D1;H1:16]>>[C:1]-[#7:2]1-[C:3]2-[C:4](-[#7:5]-[C:6]-1=[O;D1;H0:7])-[C:8]-[#16:9]-[CH;D3;+0:10]-2-[CH;D3;+0:11](-[C:12]-[C:13])-[C:14](=[O;D1;H0:15])-[O;D1;H1:16] | 95.5 | [{"value": 95.5, "product": "O=C1N([C@H]2[C@@H](N1CC1=CC=CC=C1)CSC2C(C(=O)O)CCC)CC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.5, "product": "O=C1N([C@H]2[C@@H](N1CC1=CC=CC=C1)CSC2C(C(=O)O)CCC)CC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 100 g of (3aS, 6aR)hexahydro2-oxo-1,3-dibenzylthieno[3,4-d]imidazol-4-ylidenepentanoic acid (formula I) are dissolved in 340 ml of water at 40° C., where the pH is set to 8.7 using aqueous sodium hydroxide solution. 25% by weight of 5% Pd/C are added to the solution. The mixture is subsequently hydrogenated at an H2 pr... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Monosulfide | C1[NH][C@H]2CSC[C@H]2[NH]1 | C1[NH][C@H]2CSC[C@H]2[NH]1 | c1ccccc1.C1[NH][C@H]2CSC[C@H]2[NH]1.c1ccccc1 | null | [Pd].O | null | null | CCCC(C(=O)O)=C1SC[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1>[Pd].O>CCCC(C(=O)O)C1SC[C@H]2[C@@H]1N(Cc1ccccc1)C(=O)N2Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c8877349ecd41a09bb37cf0c4de17f1 | N#CCC(C#N)=NNc1c(Cl)cc(C(F)(F)F)cc1Cl>>N#CCC(C#N)NNc1c(Cl)cc(C(F)(F)F)cc1Cl | C([O-])(O)=O.[Na+].ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NN=C(C#N)CC#N.[C-]#N.[Na+].O>>ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NNC(C#N)CC#N | [N:1]#[C:2][CH2:3][C:4]([C:5]#[N:6])=[N:7][NH:8][c:9]1[c:10]([Cl:11])[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1[Cl:20]>>[N:1]#[C:2][CH2:3][CH:4]([C:5]#[N:6])[NH:7][NH:8][c:9]1[c:10]([Cl:11])[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1[Cl:20] | N#CCC(C#N)=NNc1c(Cl)cc(C(F)(F)F)cc1Cl | N#CCC(C#N)NNc1c(Cl)cc(C(F)(F)F)cc1Cl | null | null | C(C)(=O)O | Reduction | OtherReaction | 5407f493a1ccf8dd5d07d54ae38e6a10270ea7ce5de5a6b7714c1deac546b85e | e98fc89254846fe35f9c53f13405831fb1e12dbc5358868ae840bffa7ffc2275 | c1ccccc1 | [N;D1;H0:1]#[C:2]-[C:3]-[C;H0;D3;+0:4](-[C:5]#[N;D1;H0:6])=[N;H0;D2;+0:7]-[#7:8]-[c:9]>>[N;D1;H0:1]#[C:2]-[C:3]-[CH;D3;+0:4](-[C:5]#[N;D1;H0:6])-[NH;D2;+0:7]-[#7:8]-[c:9] | 40 | [{"value": 40.0, "product": "ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NNC(C#N)CC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 40 | HOUR | 2-(2,6-Dichloro-4-trifluoromethylphenylhydrazono) succinonitrile (0.296 g, 1 mmol), sodium cyanide (0.196 g, 4 equivalents), water (1 ml) and acetic acid (5 ml) were added successively to a sealed tube. After reacting for 40 hours at 20° C., the mixture was added to saturated sodium bicarbonate solution, extracted (dic... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone | Hydrazine | null | null | c1ccccc1 | null | C(C)(=O)O | null | 40 | N#CCC(C#N)=NNc1c(Cl)cc(C(F)(F)F)cc1Cl>C(C)(=O)O>N#CCC(C#N)NNc1c(Cl)cc(C(F)(F)F)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-51889edae8a3452c876a139b2f003a44 | N#CCCNNc1c(Cl)cc(C(F)(F)F)cc1Cl>>N#CCC=NNc1c(Cl)cc(C(F)(F)F)cc1Cl.N#CCCN=Nc1c(Cl)cc(C(F)(F)F)cc1Cl | ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NNCCC#N>>ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NN=CCC#N.ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)N=NCCC#N | [N:1]#[C:2][CH2:3][CH2:4][NH:5][NH:6][c:7]1[c:8]([Cl:9])[cH:10][c:11]([C:12]([F:13])([F:15])[F:33])[cH:16][c:17]1[Cl:18]>>[N:1]#[C:2][CH2:3][CH:4]=[N: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].[N:19]#[C:20][CH2:21][CH2:22][N:23]=[N:24][c:25]1[c:26]([Cl:27])[cH:28][c:29](... | N#CCCNNc1c(Cl)cc(C(F)(F)F)cc1Cl | N#CCC=NNc1c(Cl)cc(C(F)(F)F)cc1Cl.N#CCCN=Nc1c(Cl)cc(C(F)(F)F)cc1Cl | null | null | ClC1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | ed8aad37eaaa5ec92e31575847810e2cf3e9924d0be11e1846f6a8b90af167b0 | 1dcb17eb3b544a058222c99dcf2a97e724801be2ed0154d7db881d9d0bbe9100 | c1ccccc1.c1ccccc1 | [F;D1;H0:1]-[C;H0;D4;+0:2](-[F;D1;H0:3])(-[F;H0;D1;+0:4])-[c:5](:[c:6]):[c:7].[N;D1;H0:8]#[C:9]-[C:10]-[CH2;D2;+0:11]-[NH;D2;+0:12]-[#7:13]-[c:14]>>[F;D1;H0:1]-[C;H0;D4;+0:2](-[F;D1;H0:15])(-[F;D1;H0:3])-[c:5](:[c:6]):[c:7].[N;D1;H0:8]#[C:9]-[C:10]-[CH;D2;+0:11]=[N;H0;D2;+0:12]-[#7:13]-[c:14].[F;D1;H0:16]-[C:17](-[F;D1... | null | [] | 65 | CELSIUS | null | null | Cupric chloride (0.673 g, 2.5 equivalents) was added in one portion to a solution of 3-(2,6-dichloro-4-trifluoromethylphenylhydrazino)propionitrile (0.591 g, 2 mmol) in chlorobenzene, and the mixture heated at 65° C. for 50 minutes. The reaction was judged to be complete and was cooled, washed (water), dried (magnesium... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Trifluoro group | Hydrazone.Trifluoro group.Trifluoro group.Aromatic halide.Aromatic halide.Diazene.Nitrile | null | c1ccccc1 | c1ccccc1.c1ccccc1 | Other | ClC1=CC=CC=C1 | 65 | null | N#CCCNNc1c(Cl)cc(C(F)(F)F)cc1Cl>ClC1=CC=CC=C1>N#CCC=NNc1c(Cl)cc(C(F)(F)F)cc1Cl.N#CCCN=Nc1c(Cl)cc(C(F)(F)F)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-baf1448600b24f08910c52ab2c44d07b | N#CCC(C#N)=NNc1c(Cl)cc(C(F)(F)F)cc1Cl>>N#CCC(C#N)NNc1c(Cl)cc(C(F)(F)F)cc1Cl | C([O-])(O)=O.[Na+].ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NN=C(C#N)CC#N.[C-]#N.[Na+].O>>ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NNC(C#N)CC#N | [N:1]#[C:2][CH2:3][C:4]([C:5]#[N:6])=[N:7][NH:8][c:9]1[c:10]([Cl:11])[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1[Cl:20]>>[N:1]#[C:2][CH2:3][CH:4]([C:5]#[N:6])[NH:7][NH:8][c:9]1[c:10]([Cl:11])[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][c:19]1[Cl:20] | N#CCC(C#N)=NNc1c(Cl)cc(C(F)(F)F)cc1Cl | N#CCC(C#N)NNc1c(Cl)cc(C(F)(F)F)cc1Cl | null | null | C(C)(=O)O | Reduction | OtherReaction | 5407f493a1ccf8dd5d07d54ae38e6a10270ea7ce5de5a6b7714c1deac546b85e | e98fc89254846fe35f9c53f13405831fb1e12dbc5358868ae840bffa7ffc2275 | c1ccccc1 | [N;D1;H0:1]#[C:2]-[C:3]-[C;H0;D3;+0:4](-[C:5]#[N;D1;H0:6])=[N;H0;D2;+0:7]-[#7:8]-[c:9]>>[N;D1;H0:1]#[C:2]-[C:3]-[CH;D3;+0:4](-[C:5]#[N;D1;H0:6])-[NH;D2;+0:7]-[#7:8]-[c:9] | 40 | [{"value": 40.0, "product": "ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NNC(C#N)CC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(2,6-Dichloro-4-trifluoromethylphenylhydrazono) succinonitrile (0.296 g, 1 mmol), sodium cyanide (0.196 g, 4 equivalents), water (1 ml) and acetic acid (5 ml) were added successively to a tube, which was sealed and reacted at 20° C. for 40 hours. The mixture was added to saturated sodium bicarbonate solution, extract... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone | Hydrazine | null | null | c1ccccc1 | null | C(C)(=O)O | null | null | N#CCC(C#N)=NNc1c(Cl)cc(C(F)(F)F)cc1Cl>C(C)(=O)O>N#CCC(C#N)NNc1c(Cl)cc(C(F)(F)F)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-67a56ca062ed49e28806d7fa817ae8e6 | N#CCC(C#N)NNc1c(Cl)cc(C(F)(F)F)cc1Cl>>N#Cc1cc(N)n(-c2c(Cl)cc(C(F)(F)F)cc2Cl)n1 | ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NNC(C#N)CC#N>>NC1=CC(=NN1C1=C(C=C(C=C1Cl)C(F)(F)F)Cl)C#N | [N:1]#[C:2][CH:3]([CH2:4][C:5]#[N:6])[NH:20][NH:7][c:8]1[c:9]([Cl:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][c:18]1[Cl:19]>>[N:1]#[C:2][c:3]1[cH:4][c:5]([NH2:6])[n:7](-[c:8]2[c:9]([Cl:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][c:18]2[Cl:19])[n:20]1 | N#CCC(C#N)NNc1c(Cl)cc(C(F)(F)F)cc1Cl | N#Cc1cc(N)n(-c2c(Cl)cc(C(F)(F)F)cc2Cl)n1 | null | null | ClC1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | b468450357c340324b27ad221956f278e770d5b03898c74e823c1dcc5fe3860a | 5092d92c44a94ca732d9d3d84dd7211867770f6f2163d1b48afa6352f7be4e62 | c1ccc(-n2cccn2)cc1 | [Cl;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[NH;D2;+0:5]-[NH;D2;+0:6]-[CH;D3;+0:7](-[C:8]#[N;D1;H0:9])-[CH2;D2;+0:10]-[C;H0;D2;+0:11]#[N;H0;D1;+0:12]):[c:13](-[Cl;D1;H0:14]):[c:15]>>[Cl;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[n;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[c;H0;D3;+0:7](-[C:8]#[N;D1;H0:9]):[cH;D2;+0:10]:[c;H0;D3;+0:11]:... | null | [] | null | null | null | null | A mixture of 2-(2,6-dichloro-4-trifluoromethylphenylhydrazino)succinonitrile (0.323 g) and cupric chloride (0.175 g) was heated in chlorobenzene at 60° C. for 6 hours. After filtration and evaporation, the title compound and 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole were obtained as a 7:1 mixture... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Nitrile | Primary amine | null | c1cc[nH]n1 | c1cc[nH]n1.c1ccccc1 | null | ClC1=CC=CC=C1 | null | null | N#CCC(C#N)NNc1c(Cl)cc(C(F)(F)F)cc1Cl>ClC1=CC=CC=C1>N#Cc1cc(N)n(-c2c(Cl)cc(C(F)(F)F)cc2Cl)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cb61453604094862921209455778ae62 | N#CCC(C#N)=NNc1c(Cl)cc(C(F)(F)F)cc1Cl>>N#Cc1cc(N)n(-c2c(Cl)cc(C(F)(F)F)cc2Cl)n1 | N.N.ClC1=C(C(=CC(=C1)C(F)(F)F)Cl)NN=C(C#N)CC#N>>NC1=CC(=NN1C1=C(C=C(C=C1Cl)C(F)(F)F)Cl)C#N | [N:1]#[C:2][C:3]([CH2:4][C:5]#[N:6])=[N:20][NH:7][c:8]1[c:9]([Cl:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][c:18]1[Cl:19]>>[N:1]#[C:2][c:3]1[cH:4][c:5]([NH2:6])[n:7](-[c:8]2[c:9]([Cl:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][c:18]2[Cl:19])[n:20]1 | N#CCC(C#N)=NNc1c(Cl)cc(C(F)(F)F)cc1Cl | N#Cc1cc(N)n(-c2c(Cl)cc(C(F)(F)F)cc2Cl)n1 | null | null | O.C(C)O | Aromatic Heterocycle Formation | OtherReaction | cfb4258ae32ca397a65abc21d2ec0f2a8bd6a228b05fd6c19d030e16cc6afe72 | b4269a4e7ce3c60f2dfb38f61cd23fe9d4819f05708cbaa9dd0a1418dfe3a6ec | c1ccc(-n2cccn2)cc1 | [Cl;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[NH;D2;+0:5]-[N;H0;D2;+0:6]=[C;H0;D3;+0:7](-[C:8]#[N;D1;H0:9])-[CH2;D2;+0:10]-[C;H0;D2;+0:11]#[N;H0;D1;+0:12]):[c:13](-[Cl;D1;H0:14]):[c:15]>>[Cl;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[n;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[c;H0;D3;+0:7](-[C:8]#[N;D1;H0:9]):[cH;D2;+0:10]:[c;H0;D3;+0:... | 98.7 | [{"value": 97.0, "product": "NC1=CC(=NN1C1=C(C=C(C=C1Cl)C(F)(F)F)Cl)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.7, "product": "NC1=CC(=NN1C1=C(C=C(C=C1Cl)C(F)(F)F)Cl)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | Ammonia (20 microliters of an 8% ammonia solution in water) was added to a mixture of the above 2-(2,6-dichloro-4—trifluoromethylphenylhydrazono)-succinonitrile (0.077 g) in ethanol (1 ml) and water (0.2 ml) at 0° C. After 10 minutes, the mixture was extracted (dichloromethane) and evaporated to give 5amino-3-cyano-1-(... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Nitrile | Primary amine | null | c1cc[nH]n1 | c1cc[nH]n1.c1ccccc1 | null | O.C(C)O | null | 0.166667 | N#CCC(C#N)=NNc1c(Cl)cc(C(F)(F)F)cc1Cl>O.C(C)O>N#Cc1cc(N)n(-c2c(Cl)cc(C(F)(F)F)cc2Cl)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1e075a27cd2c4e05b06018d53454909d | ClP(Cl)c1csc2ccccc12>>Pc1csc2ccccc12 | [H-].[H-].[H-].[H-].[Li+].[Al+3].C1CCOC1.ClP(C1=CSC2=C1C=CC=C2)Cl.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>>PC1=CSC2=C1C=CC=C2 | Cl[P:1](Cl)[c:2]1[cH:3][s:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12>>[PH2:1][c:2]1[cH:3][s:4][c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]12 | ClP(Cl)c1csc2ccccc12 | Pc1csc2ccccc12 | null | null | C(C)OCC.CCOCC | Functional Group Interconversion | OtherReaction | 42af6cdfb86a130c92365e01a31b50705eea7bdf12f67dc370bf24402f7ceedc | f1bbf9aa3c82f5e49be9f6d53533b6bb152f359232b6d32090c168949766aa71 | c1ccc2sccc2c1 | Cl-[P;H0;D3;+0:1](-Cl)-[c:2]1:[c:3]:[c:4]:[#16;a:5]:[c:6]:1>>[PH2;D1;+0:1]-[c:2]1:[c:3]:[c:4]:[#16;a:5]:[c:6]:1 | null | [] | null | null | null | null | Under a nitrogen atmosphere a three necked 1 L flask was charged with diethyl ether (200 ml) and a solution of LiAlH4 in THF (58 mL of 1 N solution, 58 mmol). A solution of 3-bis(chloro)phosphino benzo[d]thiophene (18.24 g, 77.6 mmol) in ether (ca. 40 mL) was added dropwise over ca. 30 minutes. An exothermic reaction t... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2sccc2c1 | Other | C(C)OCC.CCOCC | null | null | ClP(Cl)c1csc2ccccc12>C(C)OCC.CCOCC>Pc1csc2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d2db2c76d76647879b5756d327a4ecdc | CCCCCCC.CCNCC.C[C@H](O)CC[C@H](C)O.Pc1sc2ccccc2c1P.[Li][CH2]CCC>>C[C@@H]1CC[C@@H](C)P1c1sc2ccccc2c1P1[C@H](C)CC[C@H]1C | [Li]N(CC)CC.C[C@@H](CC[C@H](C)O)O.PC1=C(C2=C(S1)C=CC=C2)P.[Li]N(CC)CC.[Li]N(CC)CC.N(CC)CC.[Li]CCCC.CCCCCCC>>C[C@H]1P([C@@H](CC1)C)C1=C(C2=C(S1)C=CC=C2)P2[C@@H](CC[C@H]2C)C | CCCCCC[CH3:23].CCNC[CH3:19].O[C@@H:2]([CH3:1])[CH2:3][CH2:4][C@@H:5](O)[CH3:6].[PH2:7][c:8]1[s:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[c:16]1[PH2:17].[Li][CH2:18][CH2:20][CH2:21][CH3:22]>>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@@H:5]([CH3:6])[P:7]1[c:8]1[s:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[c:16]1[P:17]1[C@H:18... | CCCCCCC.CCNCC.C[C@H](O)CC[C@H](C)O.Pc1sc2ccccc2c1P.[Li][CH2]CCC | C[C@@H]1CC[C@@H](C)P1c1sc2ccccc2c1P1[C@H](C)CC[C@H]1C | null | null | C1CCOC1.O.C(C)OCC | C-C Coupling | OtherReaction | c862e309cff870a4a702548206f63b2de9275a484440e37597fb69ad6a3b9f8f | 6fa71b35a61c94f6fc706668cc5e5744bf730f33856b3eadbeabf253252d447a | c1ccc2c(P3CCCC3)c(P3CCCC3)sc2c1 | C-C-C-C-C-C-[CH3;D1;+0:1].C-C-N-C-[CH3;D1;+0:2].O-[C@@H;D3;+0:3](-[C;D1;H3:4])-[C:5]-[C:6]-[C@@H;D3;+0:7](-O)-[C;D1;H3:8].[CH3;D1;+0:9]-[C:10]-[C:11]-[CH2;D2;+0:12]-[Li].[PH2;D1;+0:13]-[c:14]1:[c:15]:[c:16]:[#16;a:17]:[c:18]:1-[PH2;D1;+0:19]>>[C;D1;H3:4]-[C@@H;D3;+0:3]1-[C:5]-[C:6]-[C@@H;D3;+0:7](-[C;D1;H3:8])-[P;H0;D3... | 53 | [{"value": 53.0, "product": "C[C@H]1P([C@@H](CC1)C)C1=C(C2=C(S1)C=CC=C2)P2[C@@H](CC[C@H]2C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Under argon, a degassed solution of 1.98 g (10 mmol) 2,3-bisphosphinobenzo[b]thiophene in 30 ml THF is treated with 5.5 ml (11 mmol) of a 2N solution of LiNEt2 (freshly prepared from Et2NH and 2.7 M n-BuLi/heptane) in THF. The resulting red solution is added to a degassed solution of the cyclic sulfate derived from (2S... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol.Secondary amine.Alkyl lithium | null | null | C1CC[P]C1.C1CC[P]C1 | C1CC[P]C1.c1ccc2sccc2c1.C1CC[P]C1 | HO-.Li | C1CCOC1.O.C(C)OCC | null | 2 | CCCCCCC.CCNCC.C[C@H](O)CC[C@H](C)O.Pc1sc2ccccc2c1P.[Li][CH2]CCC>C1CCOC1.O.C(C)OCC>C[C@@H]1CC[C@@H](C)P1c1sc2ccccc2c1P1[C@H](C)CC[C@H]1C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c9e588b9fb2e4e3d96164ee2aa8ac6ed | CC[C@H](O)CC[C@@H](O)CC.Pc1sc2ccccc2c1P>>CC[C@@H]1CC[C@@H](CC)P1c1sc2ccccc2c1P1[C@H](CC)CC[C@H]1CC | CC[C@@H](CC[C@H](CC)O)O.PC1=C(C2=C(S1)C=CC=C2)P>>C(C)[C@H]1P([C@@H](CC1)CC)C1=C(C2=C(S1)C=CC=C2)P2[C@@H](CC[C@H]2CC)CC | O[C@@H:3]([CH2:2][CH3:1])[CH2:4][CH2:23][C@@H:20](O)[CH2:21][CH3:22].[PH2:9][c:10]1[s:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[c:18]1[PH2:19]>>[CH3:1][CH2:2][C@@H:3]1[CH2:4][CH2:5][C@@H:6]([CH2:7][CH3:8])[P:9]1[c:10]1[s:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[c:18]1[P:19]1[C@H:20]([CH2:21][CH3:22])[CH2:23][C... | CC[C@H](O)CC[C@@H](O)CC.Pc1sc2ccccc2c1P | CC[C@@H]1CC[C@@H](CC)P1c1sc2ccccc2c1P1[C@H](CC)CC[C@H]1CC | null | null | null | C-C Coupling | OtherReaction | 945ea16d13907ab8ecd95e7bb3af650bedd656b551e6cefce2341d4ad5401cba | d31b1403224a2056c6fea4b48c2e4a296abf1f6d3f650f72956bbe0c3270c86f | c1ccc2c(P3CCCC3)c(P3CCCC3)sc2c1 | O-[C@@H;D3;+0:1](-[C:2]-[C;D1;H3:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[C@@H;D3;+0:6](-O)-[C:7]-[C;D1;H3:8].[PH2;D1;+0:9]-[c:10]1:[c:11]:[c:12]:[#16;a:13]:[c:14]:1-[PH2;D1;+0:15]>>[C:16]-[C:17]1-[C:18]-[CH2;D2;+0:4]-[C@@H;D3;+0:1](-[C:2]-[C;D1;H3:3])-[P;H0;D3;+0:9]-1-[c:10]1:[c:11]:[c:12]:[#16;a:13]:[c:14]:1-[P;H0;D3;+0:15]1... | 48 | [{"value": 48.0, "product": "C(C)[C@H]1P([C@@H](CC1)CC)C1=C(C2=C(S1)C=CC=C2)P2[C@@H](CC[C@H]2CC)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In analogy to Example 11, the cyclic sulfate derived from (3S,6S)-3,6-octanediol is reacted with 2,3-bisphosphinobenzo[b]thiophene to give the title compound in 48% yield.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Secondary alcohol | null | null | C1CC[P]C1.C1CC[P]C1 | C1CC[P]C1.c1ccc2sccc2c1.C1CC[P]C1 | null | null | null | null | CC[C@H](O)CC[C@@H](O)CC.Pc1sc2ccccc2c1P>>CC[C@@H]1CC[C@@H](CC)P1c1sc2ccccc2c1P1[C@H](CC)CC[C@H]1CC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9f2ddd4ffff34606b2cc625dff14a9fc | CN1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1>>CN1CCN(c2ccc(N=C=S)cc2)CC1 | C(=S)(N1C=NC=C1)N1C=NC=C1.CN1CCN(CC1)C1=CC=C(C=C1)N>>N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:13][cH:14]2)[CH2:15][CH2:16]1.c1cn([C:11](n2ccnc2)=[S:12])cn1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([N:10]=[C:11]=[S:12])[cH:13][cH:14]2)[CH2:15][CH2:16]1 | CN1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1 | CN1CCN(c2ccc(N=C=S)cc2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | be7cda7c305cb7fe0f9c01bbc607472f3b10db5b9ac4c3f6176bd6d49196c1b0 | b9d004d515d4691c0e9944172fdecaa5dd531c6cfbffee450da8866f92f0f7d4 | c1ccc(N2CCNCC2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:5]=[C;H0;D3;+0:6](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[S;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | 83 | [{"value": 83.0, "product": "N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | 1 | HOUR | A mixture of thiocarbonyldiimidazole (4.46 g, 25.0 mmol) (Aldrich) and N,N-dimethylformamide (20 mL) was cooled to about −15° C. and a solution of 4-(4-methyl-1-piperazinyl)benzenamine (prepared according to the procedure of Chong, W. K. et al. WO9921845; 4.78 g, 25.0 mmol) was added over a period of 30 min. The coolin... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Thiocarbonyl | Isothiocyanate | c1c[nH]cn1.c1c[nH]cn1 | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | CN(C=O)C | -15 | 1 | CN1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1>CN(C=O)C>CN1CCN(c2ccc(N=C=S)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7fc712df9bea40238aa90ddb61a7176d | CN1CCNCC1.O=[N+]([O-])c1ccc(F)c(F)c1>>CN1CCN(c2ccc([N+](=O)[O-])cc2F)CC1 | FC=1C=C(C=CC1F)[N+](=O)[O-].CN1CCNCC1>>FC1=C(C=CC(=C1)[N+](=O)[O-])N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:16][CH2:17]1.F[c:6]1[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]1[F:15]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]2[F:15])[CH2:16][CH2:17]1 | CN1CCNCC1.O=[N+]([O-])c1ccc(F)c(F)c1 | CN1CCN(c2ccc([N+](=O)[O-])cc2F)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | d687b31bdda9f407fdde6ca57e67eee0681e173646c617afef7770c56d05bab9 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCNCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1):[c:2]:[c:3] | 97 | [{"value": 97.0, "product": "FC1=C(C=CC(=C1)[N+](=O)[O-])N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.0, "product": "FC1=C(C=CC(=C1)[N+](=O)[O-])N1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 3,4-difluoronitrobenzene (12.00 g, 75.4 mmol) (Aldrich) and N-methylpiperazine (18.89 g, 188.6 mmol) in acetonitrile (150 mL) was heated at reflux for 3 h. The reaction mixture was allowed to stand overnight at room temperature, then the solvent was evaporated under reduced pressure and the residue was pa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | HF | C(C)#N | null | 8 | CN1CCNCC1.O=[N+]([O-])c1ccc(F)c(F)c1>C(C)#N>CN1CCN(c2ccc([N+](=O)[O-])cc2F)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-864b47b038fb440aa3f650a6dea2c1e2 | CN1CCN(c2ccc([N+](=O)[O-])cc2F)CC1>>CN1CCN(c2ccc(N)cc2F)CC1 | FC1=C(C=CC(=C1)[N+](=O)[O-])N1CCN(CC1)C>>FC=1C=C(C=CC1N1CCN(CC1)C)N | O=[N+:10]([O-])[c:9]1[cH:8][cH:7][c:6]([N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:15][CH2:14]2)[c:12]([F:13])[cH:11]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:11][c:12]2[F:13])[CH2:14][CH2:15]1 | CN1CCN(c2ccc([N+](=O)[O-])cc2F)CC1 | CN1CCN(c2ccc(N)cc2F)CC1 | null | [Pd] | C(C)(=O)OCC.C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCNCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 93 | [{"value": 93.0, "product": "FC=1C=C(C=CC1N1CCN(CC1)C)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.6, "product": "FC=1C=C(C=CC1N1CCN(CC1)C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-(2-fluoro-4-nitrophenyl)-4-methylpiperazine (5.00 g, 20.9 mmol) (from Step A above) and 10% palladium-on-carbon (0.20 g, 0.2 mmol) in ethyl acetate (100 mL) and ethanol (50 mL) was hydrogenated at 50 psi in a Parr shaker for 4 h. The mixture was filtered through Celite™. The Celite™ was washed with ethy... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | [Pd].C(C)(=O)OCC.C(C)O | null | null | CN1CCN(c2ccc([N+](=O)[O-])cc2F)CC1>[Pd].C(C)(=O)OCC.C(C)O>CN1CCN(c2ccc(N)cc2F)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8e88da186bb64330afe884ecd3c3eb32 | CN1CCN(c2ccc(N)cc2F)CC1.S=C(c1ncc[nH]1)c1ncc[nH]1>>CN1CCN(c2ccc(N=C=S)cc2F)CC1 | FC=1C=C(C=CC1N1CCN(CC1)C)N.C(=S)(C=1NC=CN1)C=1NC=CN1>>FC1=C(C=CC(=C1)N=C=S)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:13][c:14]2[F:15])[CH2:16][CH2:17]1.c1c[nH]c([C:11](c2ncc[nH]2)=[S:12])n1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([N:10]=[C:11]=[S:12])[cH:13][c:14]2[F:15])[CH2:16][CH2:17]1 | CN1CCN(c2ccc(N)cc2F)CC1.S=C(c1ncc[nH]1)c1ncc[nH]1 | CN1CCN(c2ccc(N=C=S)cc2F)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | be7cda7c305cb7fe0f9c01bbc607472f3b10db5b9ac4c3f6176bd6d49196c1b0 | b9d004d515d4691c0e9944172fdecaa5dd531c6cfbffee450da8866f92f0f7d4 | c1ccc(N2CCNCC2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:5]=[C;H0;D3;+0:6](-c1:[nH]:c:c:n:1)-c1:[nH]:c:c:n:1>>[S;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | Thiocarbonyl diimidazole (3.00 g, 3.53 mmol) (Aldrich) was dissolved in N,N-dimethylformamide (10 mL) and the solution was cooled to −10° C. (ice/acetone bath). A solution of 3-fluoro-4-(4-methyl-1-piperazinyl) benzenamine (2.26 g, 10.8 mmol) (from Step B above) in N,N-dimethylformamide (30 mL) was added over a period ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Thiocarbonyl | Isothiocyanate | c1c[nH]cn1.c1c[nH]cn1 | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | CN(C=O)C | null | 8 | CN1CCN(c2ccc(N)cc2F)CC1.S=C(c1ncc[nH]1)c1ncc[nH]1>CN(C=O)C>CN1CCN(c2ccc(N=C=S)cc2F)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9f2a80a91dcc4887a781077f3e4406f3 | CC(C)N1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1>>CC(C)N1CCN(c2ccc(N=C=S)cc2)CC1 | CC(C)N1CCN(CC1)C1=CC=C(C=C1)N.C(=S)(N1C=NC=C1)N1C=NC=C1>>N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C(C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:15][cH:16]2)[CH2:17][CH2:18]1.c1cn([C:13](n2ccnc2)=[S:14])cn1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([N:12]=[C:13]=[S:14])[cH:15][cH:16]2)[CH2:17][CH2:18]1 | CC(C)N1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1 | CC(C)N1CCN(c2ccc(N=C=S)cc2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | be7cda7c305cb7fe0f9c01bbc607472f3b10db5b9ac4c3f6176bd6d49196c1b0 | b9d004d515d4691c0e9944172fdecaa5dd531c6cfbffee450da8866f92f0f7d4 | c1ccc(N2CCNCC2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:5]=[C;H0;D3;+0:6](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[S;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | 101.3 | [{"value": 101.3, "product": "N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | 20 | MINUTE | A solution of 4-[4-(1-methylethyl)-1-piperazinyl]benzenamine (1.6 g,˜6.8 mmol) (from Step B above) in N,N-dimethylformamide (25 mL) was added dropwise over 20 min to a cooled (−15° C.) solution of thiocarbonyldiimidazole (1.4 g, 7.7 mmol) (Aldrich) in N,N-dimethylformamide (30 mL). After the addition was complete, the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Thiocarbonyl | Isothiocyanate | c1c[nH]cn1.c1c[nH]cn1 | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | CN(C=O)C | -15 | 0.333333 | CC(C)N1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1>CN(C=O)C>CC(C)N1CCN(c2ccc(N=C=S)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-994cbfeb630d41b6b2862208213baf98 | CC(=O)Cl.O=[N+]([O-])c1ccc(N2CCNCC2)cc1>>CC(=O)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1 | C([O-])([O-])=O.[K+].[K+].C(C)(=O)Cl.[N+](=O)([O-])C1=CC=C(C=C1)N1CCNCC1.C([O-])([O-])=O.[K+].[K+].C(C)(=O)Cl>>C(C)(=O)N1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-] | Cl[C:2]([CH3:1])=[O:3].[NH:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[CH2:17][CH2:18]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[CH2:17][CH2:18]1 | CC(=O)Cl.O=[N+]([O-])c1ccc(N2CCNCC2)cc1 | CC(=O)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | 6dd420fad17fb719b6bd840e8952a8d7b2fb24721f86f8b8f9c697a36eb97ec3 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(N2CCNCC2)cc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 722.1 | [{"value": 72.0, "product": "C(C)(=O)N1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 722.1, "product": "C(C)(=O)N1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Powdered potassium carbonate (276 mg, 2 mmol) and then acetyl chloride (0.14 mL, 2 mmol) were added to a solution of 1-(4-nitrophenyl) piperazine (2.1 g, 1 mmol) (Acros Organics) in dichloromethane (75 mL). The mixture was stirred at room temperature overnight and then further quantities of powdered potassium carbonate... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | HCl | ClCCl | null | 8 | CC(=O)Cl.O=[N+]([O-])c1ccc(N2CCNCC2)cc1>ClCCl>CC(=O)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c84ff7750f7042e88d7b296e98f6f5f4 | CC(=O)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1>>CC(=O)N1CCN(c2ccc(N)cc2)CC1 | C(C)(=O)N1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-]>>C(C)(=O)N1CCN(CC1)C1=CC=C(C=C1)N | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]([N:7]2[CH2:6][CH2:5][N:4]([C:2]([CH3:1])=[O:3])[CH2:16][CH2:15]2)[cH:14][cH:13]1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:13][cH:14]2)[CH2:15][CH2:16]1 | CC(=O)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1 | CC(=O)N1CCN(c2ccc(N)cc2)CC1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCNCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 63.3 | [{"value": 63.0, "product": "C(C)(=O)N1CCN(CC1)C1=CC=C(C=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.3, "product": "C(C)(=O)N1CCN(CC1)C1=CC=C(C=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1-acetyl-4-(4-nitrophenyl)piperazine (1.8 g, 7.2 mmol) (from Step A above) and 10% palladium-on-charcoal in ethanol (50 mL) was hydrogenated at room temperature and atmospheric pressure overnight. The catalyst was filtered off and the filter cake washed thoroughly with ethanol. The mixture was evaporated u... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | [Pd].C(C)O | null | null | CC(=O)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1>[Pd].C(C)O>CC(=O)N1CCN(c2ccc(N)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-791ac1550fd64af8a5667939b1f90372 | CC(=O)N1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1>>CC(=O)N1CCN(c2ccc(N=C=S)cc2)CC1 | C(C)(=O)N1CCN(CC1)C1=CC=C(C=C1)N.C(=S)(N1C=NC=C1)N1C=NC=C1>>C(C)(=O)N1CCN(CC1)C1=CC=C(C=C1)N=C=S | [CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:15][cH:16]2)[CH2:17][CH2:18]1.c1cn([C:13](n2ccnc2)=[S:14])cn1>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([N:12]=[C:13]=[S:14])[cH:15][cH:16]2)[CH2:17][CH2:18]1 | CC(=O)N1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1 | CC(=O)N1CCN(c2ccc(N=C=S)cc2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | be7cda7c305cb7fe0f9c01bbc607472f3b10db5b9ac4c3f6176bd6d49196c1b0 | b9d004d515d4691c0e9944172fdecaa5dd531c6cfbffee450da8866f92f0f7d4 | c1ccc(N2CCNCC2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:5]=[C;H0;D3;+0:6](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[S;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | 84 | [{"value": 84.0, "product": "C(C)(=O)N1CCN(CC1)C1=CC=C(C=C1)N=C=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.2, "product": "C(C)(=O)N1CCN(CC1)C1=CC=C(C=C1)N=C=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | 30 | MINUTE | A solution of 1-acetyl-4-(4-aminophenyl)piperazine (1.0 g, 4.6 mmol) (from Step B above) in N,N-dimethylformamide (10 mL) was added dropwise to a cooled (−15° C.) solution of thiocarbonyldiimidazole (855 mg, 4.8 mmol) in N,N-dimethylformamide (10 mL). After the addition was complete, the mixture was stirred at −15° C. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Thiocarbonyl | Isothiocyanate | c1c[nH]cn1.c1c[nH]cn1 | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | CN(C=O)C | -15 | 0.5 | CC(=O)N1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1>CN(C=O)C>CC(=O)N1CCN(c2ccc(N=C=S)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-63144ce9652240199f91e9d2e6bc1107 | O=[N+]([O-])c1ccc(N2CCN(CCO)CC2)cc1.[N-]=C=S>>OCCN1CCN(c2ccc(N=C=S)cc2)CC1 | [N+](=O)([O-])C1=CC=C(C=C1)N1CCN(CC1)CCO.[N-]=C=S>>OCCN1CCN(CC1)C1=CC=C(C=C1)N=C=S | O=[N+]([O-])[c:11]1[cH:10][cH:9][c:8]([N:7]2[CH2:6][CH2:5][N:4]([CH2:3][CH2:2][OH:1])[CH2:18][CH2:17]2)[cH:16][cH:15]1.[N-:12]=[C:13]=[S:14]>>[OH:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([N:12]=[C:13]=[S:14])[cH:15][cH:16]2)[CH2:17][CH2:18]1 | O=[N+]([O-])c1ccc(N2CCN(CCO)CC2)cc1.[N-]=C=S | OCCN1CCN(c2ccc(N=C=S)cc2)CC1 | null | null | null | Functional Group Interconversion | OtherReaction | c2b664bf7684468a37396b968ac0af317a7e2289f2edcfb8b7ab78ab404e94b4 | 305b6f3127a1d497f5798d688e7949ef02b1f99b0e5e183d105619e0875515fa | c1ccc(N2CCNCC2)cc1 | O=[N+](-[O-])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[N-;H0;D1:6]=[C:7]=[S;D1;H0:8]>>[S;D1;H0:8]=[C:7]=[N;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | This compound was prepared from 4-(4-nitrophenyl)-1-piperazine-ethanol (Bionet Research Ltd.) using the hydrogenation and isothiocyanate-forming reactions used in Example 4.
Conditions: See reaction.notes.procedure_details.
Workup: forming reactions | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Isothiocyanate | c1ccccc1 | c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | Other | null | null | null | O=[N+]([O-])c1ccc(N2CCN(CCO)CC2)cc1.[N-]=C=S>>OCCN1CCN(c2ccc(N=C=S)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-24cd7e80c0804870b102321d8cc9cb2e | CC(C)(C)OC(=O)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1>>CC(C)(C)OC(=O)N1CCN(c2ccc(N)cc2)CC1 | [N+](=O)([O-])C1=CC=C(C=C1)N1CCN(CC1)C(=O)OC(C)(C)C.[H][H]>>NC1=CC=C(C=C1)N1CCN(CC1)C(=O)OC(C)(C)C | O=[N+:16]([O-])[c:15]1[cH:14][cH:13][c:12]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:20][CH2:19]2)[cH:18][cH:17]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([NH2:16])[cH:17][cH:18]2)[CH2:19][CH2:20]1 | CC(C)(C)OC(=O)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1 | CC(C)(C)OC(=O)N1CCN(c2ccc(N)cc2)CC1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(N2CCNCC2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 99.8 | [{"value": 98.0, "product": "NC1=CC=C(C=C1)N1CCN(CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.8, "product": "NC1=CC=C(C=C1)N1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-(4-Nitrophenyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (20 g, 65 mmol) was dissolved in anhydrous ethanol (250 mL) and 10% Pd/C (1.8 g) was added. The mixture was stirred for 1.5 h under 10 psi of hydrogen and filtered through a Celite pad. The pad was washed with ethyl acetate (3×100 mL) and the combin... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | [Pd].C(C)O | null | null | CC(C)(C)OC(=O)N1CCN(c2ccc([N+](=O)[O-])cc2)CC1>[Pd].C(C)O>CC(C)(C)OC(=O)N1CCN(c2ccc(N)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-66c9ae911dbb4a32a0ac6929b789a6cc | CC(C)(C)OC(=O)N1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1>>CC(C)(C)OC(=O)N1CCN(c2ccc(N=C=S)cc2)CC1 | NC1=CC=C(C=C1)N1CCN(CC1)C(=O)OC(C)(C)C.C(=S)(N1C=NC=C1)N1C=NC=C1>>N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][c:15]([NH2:16])[cH:19][cH:20]2)[CH2:21][CH2:22]1.c1cn([C:17](n2ccnc2)=[S:18])cn1>>[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][c:15]([N:16]=[C:17]=[S:18])[cH:19][cH:20]2... | CC(C)(C)OC(=O)N1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1 | CC(C)(C)OC(=O)N1CCN(c2ccc(N=C=S)cc2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | be7cda7c305cb7fe0f9c01bbc607472f3b10db5b9ac4c3f6176bd6d49196c1b0 | b9d004d515d4691c0e9944172fdecaa5dd531c6cfbffee450da8866f92f0f7d4 | c1ccc(N2CCNCC2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:5]=[C;H0;D3;+0:6](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[S;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | 104.2 | [{"value": 94.0, "product": "N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.2, "product": "N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 4-(4-aminophenyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (15 g, 54.1 mmol) (from Step B above) in N,N-dimethylformamide (120 mL) was added dropwise to a cooled (−15° C.) solution of 1,1′-thiocarbonyldiimidazole (9.66 g, 54.2 mmol) (Aldrich) in N,N-dimethylformamide (40 mL). After the additio... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Thiocarbonyl | Isothiocyanate | c1c[nH]cn1.c1c[nH]cn1 | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | CN(C=O)C | null | 1 | CC(C)(C)OC(=O)N1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1>CN(C=O)C>CC(C)(C)OC(=O)N1CCN(c2ccc(N=C=S)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ff4256aaf0c04c6c9ceb8c97dc41cecd | O=C(c1ccc(N2CCCCC2)cc1)C(Br)Br>>O=C(CBr)c1ccc(N2CCCCC2)cc1 | C(C)OP(OCC)[O-].C(C)N(CC)CC.BrC(C(=O)C1=CC=C(C=C1)N1CCCCC1)Br>>BrCC(=O)C1=CC=C(C=C1)N1CCCCC1 | Br[CH:3]([C:2](=[O:1])[c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][cH:16]1)[Br:4]>>[O:1]=[C:2]([CH2:3][Br:4])[c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[cH:15][cH:16]1 | O=C(c1ccc(N2CCCCC2)cc1)C(Br)Br | O=C(CBr)c1ccc(N2CCCCC2)cc1 | null | null | O1CCCC1 | Functional Group Interconversion | Dehalogenation | 77c4006b61feafdadb38a3464a8de1ee490b61d0da0c13bca01b4c6c32c9e17b | 6057d7fb75624930c9e41a46967dce14902ce53987bcfcd5587c4c1a79bea4df | c1ccc(N2CCCCC2)cc1 | Br-[CH;D3;+0:1](-[Br;D1;H0:2])-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;D1;H0:2]-[CH2;D2;+0:1]-[C:3](=[O;D1;H0:4])-[c:5] | 100 | [{"value": 100.0, "product": "BrCC(=O)C1=CC=C(C=C1)N1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.2, "product": "BrCC(=O)C1=CC=C(C=C1)N1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | 2,2-Dibromo-1-[4-(1-piperidinyl)phenyl]ethanone (3 g, 8.3 mmol) (from Step A above) was dissolved in tetrahydrofuran (15 mL), and cooled to 0° C. To the resulting solution were added dropwise diethylphosphite (1.13 mL, 8.7 mmol) and triethylamine (1.21 mL, 8.7 mmol) in tetrahydrofuran (7 mL) at 0° C. with stirring. The... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide | Primary halide | null | null | c1ccccc1.C1CC[NH]CC1 | Br- | O1CCCC1 | 0 | null | O=C(c1ccc(N2CCCCC2)cc1)C(Br)Br>O1CCCC1>O=C(CBr)c1ccc(N2CCCCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-73931fa5a60e46348d2c319123fbab8b | CC(=O)c1ccc(N2CCOCC2)cc1.O=C(CBr)c1ccc(N2CCCCC2)cc1>>O=C(CBr)c1ccc(N2CCOCC2)cc1 | N1(CCOCC1)C1=CC=C(C=C1)C(C)=O.BrCC(=O)C1=CC=C(C=C1)N1CCCCC1>>BrCC(=O)C1=CC=C(C=C1)N1CCOCC1 | CC(=O)c1c[cH:7][c:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15]c1.c1c(N2CCCCC2)c[cH:16][c:5]([C:2](=[O:1])[CH2:3][Br:4])[cH:6]1>>[O:1]=[C:2]([CH2:3][Br:4])[c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15][cH:16]1 | CC(=O)c1ccc(N2CCOCC2)cc1.O=C(CBr)c1ccc(N2CCCCC2)cc1 | O=C(CBr)c1ccc(N2CCOCC2)cc1 | null | null | null | Miscellaneous | Bromination | bc6ef9b1f3fe2b0e61b094d3e6aa4b12aede4c936631a3accb5245309189a7bd | 592dfb5f38ca3726bb7bcfb5eeb55519b727530a542db3567e54f180d6649952 | c1ccc(N2CCOCC2)cc1 | C-C(=O)-c1:c:[cH;D2;+0:1]:[c:2](-[#7:3]):[cH;D2;+0:4]:c:1.[C:5]-[C:6](=[O;D1;H0:7])-[c:8]1:[cH;D2;+0:9]:c:c(-N2-C-C-C-C-C-2):c:[cH;D2;+0:10]:1>>[#7:3]-[c:2]1:[cH;D2;+0:1]:[cH;D2;+0:9]:[c:8](-[C:6](-[C:5])=[O;D1;H0:7]):[cH;D2;+0:10]:[cH;D2;+0:4]:1 | null | [] | null | null | null | null | This compound was prepared from 1-[4-(4-morpholinyl)phenyl]ethanone (Aldrich) by procedures analogous to those used to prepare 2-bromo-1-[4-(1-piperidinyl)phenyl]ethanone (Example 7).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Tertiary amine | null | c1ccccc1.c1ccccc1.C1CCNCC1 | c1ccccc1 | c1ccccc1.C1COCC[NH]1 | HO- | null | null | null | CC(=O)c1ccc(N2CCOCC2)cc1.O=C(CBr)c1ccc(N2CCCCC2)cc1>>O=C(CBr)c1ccc(N2CCOCC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f5d11cfe3cd8412daee3285f06654237 | BrBr.CC(=O)Nc1ccc(C(C)=O)cc1>>CC(=O)Nc1ccc(C(=O)CBr)cc1 | BrBr.C(C)(=O)C1=CC=C(C=C1)NC(C)=O.C(C)(=O)O>>BrCC(=O)C1=CC=C(C=C1)NC(C)=O | Br[Br:12].[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[CH3:11])[cH:13][cH:14]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([C:9](=[O:10])[CH2:11][Br:12])[cH:13][cH:14]1 | BrBr.CC(=O)Nc1ccc(C(C)=O)cc1 | CC(=O)Nc1ccc(C(=O)CBr)cc1 | null | null | C(Cl)(Cl)(Cl)Cl | 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] | 97.6 | [{"value": 97.6, "product": "BrCC(=O)C1=CC=C(C=C1)NC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of bromine (0.31 mL, 5.9 mmol) in carbon tetrachloride (10 mL) was added to a suspension of N-(4-acetylphenyl)acetamide (1 g, 5.6 mmol) (Lancaster Synthesis) in carbon tetrachloride (20 mL). The reaction mixture was stirred for several hours but TLC indicated only starting material. Acetic acid (10 mL) was a... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | C(Cl)(Cl)(Cl)Cl | null | null | BrBr.CC(=O)Nc1ccc(C(C)=O)cc1>C(Cl)(Cl)(Cl)Cl>CC(=O)Nc1ccc(C(=O)CBr)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1467451901b34110b095a0f9bc4d4385 | BrBr.CC(=O)c1ccc(O)cc1>>O=C(CBr)c1ccc(O)cc1 | CC(=O)C=1C=CC(=CC1)O.BrBr>>BrCC(=O)C1=CC=C(C=C1)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 | O1CCOCC1 | 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] | 44 | [{"value": 44.0, "product": "BrCC(=O)C1=CC=C(C=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.0, "product": "BrCC(=O)C1=CC=C(C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 4-hydroxyacetophenone (2.5 g, 18.3 mmol) (Aldrich) in dioxane (10 mL) was added dropwise a solution of bromine (3.22 g, 20.1 mmol) in dioxane (20 mL). After stirring for 10 minutes, the mixture was concentrated in vacuo and the residue was recrystalized from methanol to provide 2-bromo-1-(4-hydroxyphen... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | O1CCOCC1 | null | 0.166667 | BrBr.CC(=O)c1ccc(O)cc1>O1CCOCC1>O=C(CBr)c1ccc(O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a2a922a5821941fc85660d7e312d45ad | BrBr.COc1ccc(C(C)=O)cc1F>>COc1ccc(C(=O)CBr)cc1F | FC=1C=C(C=CC1OC)C(C)=O.BrBr>>BrCC(=O)C1=CC(=C(C=C1)OC)F | Br[Br:10].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH3:9])[cH:11][c:12]1[F:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[CH2:9][Br:10])[cH:11][c:12]1[F:13] | BrBr.COc1ccc(C(C)=O)cc1F | COc1ccc(C(=O)CBr)cc1F | null | null | O1CCOCC1 | 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] | 63 | [{"value": 63.0, "product": "BrCC(=O)C1=CC(=C(C=C1)OC)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.4, "product": "BrCC(=O)C1=CC(=C(C=C1)OC)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 3′-fluoro-4′-methoxyacetophenone (1 g, 5.9 mmol) (Aldrich) in dioxane (10 mL) was added dropwise a solution of bromine (1.13 g, 7.1 mmol) in dioxane (30 mL). After stirring for 10 minutes, the mixture was concentrated in vacuo and the residue was purified by flash chromatography, with 10:4 hexanes/dich... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | O1CCOCC1 | null | 0.166667 | BrBr.COc1ccc(C(C)=O)cc1F>O1CCOCC1>COc1ccc(C(=O)CBr)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b766bbeecace419eaa52b615ff7cd9e8 | BrBr.CC(=O)c1cc(F)cc(F)c1>>O=C(CBr)c1cc(F)cc(F)c1 | FC=1C=C(C=C(C1)F)C(C)=O.BrBr>>BrCC(=O)C1=CC(=CC(=C1)F)F | Br[Br:4].[O:1]=[C:2]([CH3:3])[c:5]1[cH:6][c:7]([F:8])[cH:9][c:10]([F:11])[cH:12]1>>[O:1]=[C:2]([CH2:3][Br:4])[c:5]1[cH:6][c:7]([F:8])[cH:9][c:10]([F:11])[cH:12]1 | BrBr.CC(=O)c1cc(F)cc(F)c1 | O=C(CBr)c1cc(F)cc(F)c1 | null | null | O1CCOCC1 | 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] | 64.3 | [{"value": 64.0, "product": "BrCC(=O)C1=CC(=CC(=C1)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.3, "product": "BrCC(=O)C1=CC(=CC(=C1)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To a solution of 3′,5′-difluoroacetophenone (3 g, 19.2 mmol) (Lancaster Synthesis) in dioxane (30 mL) was added dropwise a solution of bromine (3.67 g, 23 mmol) in dioxane (75 mL). After stirring for 10 minutes, the mixture was concentrated in vacuo and the residue was purified by flash chromatography, with 10:2 hexane... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | O1CCOCC1 | null | 0.166667 | BrBr.CC(=O)c1cc(F)cc(F)c1>O1CCOCC1>O=C(CBr)c1cc(F)cc(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0384dff13c2340f491f72741cfa3d6a8 | CCC(C)N1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1>>CCC(C)N1CCN(c2ccc(N=C=S)cc2)CC1 | C(C)(CC)N1CCN(CC1)C1=CC=C(C=C1)N.C(=S)(N1C=NC=C1)N1C=NC=C1>>N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C(C)CC | [CH3:1][CH2:2][CH:3]([CH3:4])[N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:16][cH:17]2)[CH2:18][CH2:19]1.c1cn([C:14](n2ccnc2)=[S:15])cn1>>[CH3:1][CH2:2][CH:3]([CH3:4])[N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([N:13]=[C:14]=[S:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1 | CCC(C)N1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1 | CCC(C)N1CCN(c2ccc(N=C=S)cc2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | be7cda7c305cb7fe0f9c01bbc607472f3b10db5b9ac4c3f6176bd6d49196c1b0 | b9d004d515d4691c0e9944172fdecaa5dd531c6cfbffee450da8866f92f0f7d4 | c1ccc(N2CCNCC2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:5]=[C;H0;D3;+0:6](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[S;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | 87.1 | [{"value": 87.0, "product": "N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C(C)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.1, "product": "N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C(C)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | 20 | MINUTE | A solution of 4-[4-(sec-butyl)-1-piperazinyl]benzenamine (3.5 g, 15 mmol) (from Step B above) in N,N-dimethylformamide (40 mL) was added dropwise over 20 min to a cooled (−15° C.) solution of thiocarbonyldiimidazole (2.68 g, 15.03 mmol) (Aldrich) in N,N-dimethylformamide (15 mL). After the addition was complete, the mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Thiocarbonyl | Isothiocyanate | c1c[nH]cn1.c1c[nH]cn1 | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | CN(C=O)C | -15 | 0.333333 | CCC(C)N1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1>CN(C=O)C>CCC(C)N1CCN(c2ccc(N=C=S)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e01217a216ad48d18573a7662bc91efb | IC1CCCC1.O=[N+]([O-])c1ccc(N2CCNCC2)cc1>>O=[N+]([O-])c1ccc(N2CCN(C3CCCC3)CC2)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)N1CCNCC1.C([O-])([O-])=O.[K+].[K+].IC1CCCC1.C1COCCOCCOCCOCCOCCO1>>C1(CCCC1)N1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-] | I[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][NH:11][CH2:17][CH2:18]2)[cH:19][cH:20]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[CH2:17][CH2:18]2)[cH:19][cH:20]1 | IC1CCCC1.O=[N+]([O-])c1ccc(N2CCNCC2)cc1 | O=[N+]([O-])c1ccc(N2CCN(C3CCCC3)CC2)cc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b79569f0a031da0628617165b9a7f776b7e88b89318685d908026782e56a6194 | fb63ba09935e18320be03869002f6d5d0f0321fe7dbcd94a5ae956c3effd182d | c1ccc(N2CCN(C3CCCC3)CC2)cc1 | I-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1.[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#7:6]1-[C:7]-[C:8]-[N;H0;D3;+0:9](-[CH;D3;+0:1]2-[C:2]-[C:3]-[C:4]-[C:5]-2)-[C:10]-[C:11]-1 | null | [] | null | null | null | null | A mixture of 1-(4-nitrophenyl)piperazine (12 g, 57.9 mmol) (Acros Organics), powdered potassium carbonate (5.4 g, 39 mmol), iodocyclopentane (7 mL, 60.8 mmol) (Aldrich) and a catalytic amount of 18-crown-6 in acetonitrile (90 mL) was heated at reflux overnight. The mixture was filtered, and the filter cake was washed w... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary amine | Tertiary amine | C1CCCC1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.C1CCCC1 | c1ccccc1.C1C[NH]CC[NH]1.C1CCCC1 | HI | C(C)#N | null | null | IC1CCCC1.O=[N+]([O-])c1ccc(N2CCNCC2)cc1>C(C)#N>O=[N+]([O-])c1ccc(N2CCN(C3CCCC3)CC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-712de18a6af24ee08e2c057d57d8ba1f | Nc1ccc(N2CCN(C3CCCC3)CC2)cc1.S=C(n1ccnc1)n1ccnc1>>S=C=Nc1ccc(N2CCN(C3CCCC3)CC2)cc1 | C1(CCCC1)N1CCN(CC1)C1=CC=C(C=C1)N.C(=S)(N1C=NC=C1)N1C=NC=C1>>C1(CCCC1)N1CCN(CC1)C1=CC=C(C=C1)N=C=S | [NH2:3][c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[CH2:17][CH2:18]2)[cH:19][cH:20]1.c1cn([C:2](n2ccnc2)=[S:1])cn1>>[S:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[CH2:17][CH2:18]2)[cH:19][cH:20]1 | Nc1ccc(N2CCN(C3CCCC3)CC2)cc1.S=C(n1ccnc1)n1ccnc1 | S=C=Nc1ccc(N2CCN(C3CCCC3)CC2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | be7cda7c305cb7fe0f9c01bbc607472f3b10db5b9ac4c3f6176bd6d49196c1b0 | b9d004d515d4691c0e9944172fdecaa5dd531c6cfbffee450da8866f92f0f7d4 | c1ccc(N2CCN(C3CCCC3)CC2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:5]=[C;H0;D3;+0:6](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[S;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | 93.2 | [{"value": 93.0, "product": "C1(CCCC1)N1CCN(CC1)C1=CC=C(C=C1)N=C=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.2, "product": "C1(CCCC1)N1CCN(CC1)C1=CC=C(C=C1)N=C=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | 20 | MINUTE | A solution of 4-[4-(1-cyclopentyl)-1-piperazinyl]benzenamine (5.7 g, 22.4 mmol) (from Step B above) in N,N-dimethylformamide (75 mL) was added dropwise over 20 min to a cooled (−15° C.) solution of thiocarbonyldiimidazole (4 g, 22.5 mmol) (Aldrich) in N,N-dimethylformamide (40 mL). After the addition was complete, the ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Thiocarbonyl | Isothiocyanate | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1.C1C[NH]CC[NH]1.C1CCCC1 | Other | CN(C=O)C | -15 | 0.333333 | Nc1ccc(N2CCN(C3CCCC3)CC2)cc1.S=C(n1ccnc1)n1ccnc1>CN(C=O)C>S=C=Nc1ccc(N2CCN(C3CCCC3)CC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4754a8151d09420396863f18deb623d8 | CC(C)CI.O=[N+]([O-])c1ccc(N2CCNCC2)cc1>>CC(C)CN1CCN(c2ccc([N+](=O)[O-])cc2)CC1 | [N+](=O)([O-])C1=CC=C(C=C1)N1CCNCC1.C([O-])([O-])=O.[K+].[K+].ICC(C)C.C1COCCOCCOCCOCCOCCO1>>C(C(C)C)N1CCN(CC1)C1=CC=C(C=C1)[N+](=O)[O-] | I[CH2:4][CH:2]([CH3:1])[CH3:3].[NH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1 | CC(C)CI.O=[N+]([O-])c1ccc(N2CCNCC2)cc1 | CC(C)CN1CCN(c2ccc([N+](=O)[O-])cc2)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(N2CCNCC2)cc1 | I-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1 | null | [] | null | null | null | null | A mixture of 1-(4-nitrophenyl)piperazine (8 g, 38.6 mmol) (Acros Organics), powdered potassium carbonate (3.58 g, 25.98 mmol), 1-Iodo-2-methylpropane (4.66 ml, 40.5 mmol), and a catalytic amount of 18-crown-6 in acetonitrile (60 mL) was heated at reflux overnight. The mixture was filtered, and the filter cake was washe... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | HI | C(C)#N | null | null | CC(C)CI.O=[N+]([O-])c1ccc(N2CCNCC2)cc1>C(C)#N>CC(C)CN1CCN(c2ccc([N+](=O)[O-])cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-62e20fc7b1c54fb7b05947ef301d624f | CC(C)CN1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1>>CC(C)CN1CCN(c2ccc(N=C=S)cc2)CC1 | C(C(C)C)N1CCN(CC1)C1=CC=C(C=C1)N.C(=S)(N1C=NC=C1)N1C=NC=C1>>N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)CC(C)C | [CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([NH2:13])[cH:16][cH:17]2)[CH2:18][CH2:19]1.c1cn([C:14](n2ccnc2)=[S:15])cn1>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([N:13]=[C:14]=[S:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1 | CC(C)CN1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1 | CC(C)CN1CCN(c2ccc(N=C=S)cc2)CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | be7cda7c305cb7fe0f9c01bbc607472f3b10db5b9ac4c3f6176bd6d49196c1b0 | b9d004d515d4691c0e9944172fdecaa5dd531c6cfbffee450da8866f92f0f7d4 | c1ccc(N2CCNCC2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:5]=[C;H0;D3;+0:6](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[S;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | 87 | [{"value": 87.0, "product": "N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)CC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.0, "product": "N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)CC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | 20 | MINUTE | A solution of 4-[4-(isobutyl)-1-piperazinyl]benzenamine (7.8 g, 33.4 mmol) (from Step B above) in N,N-dimethylformamide (75 mL) was added dropwise over 20 min to a cooled (−15° C.) solution of thiocarbonyldiimidazole (5.97 g, 33.5 mmol) (Aldrich) in N,N-dimethylformamide (25 mL). After the addition was complete, the mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Thiocarbonyl | Isothiocyanate | c1c[nH]cn1.c1c[nH]cn1 | null | C1C[NH]CC[NH]1.c1ccccc1 | Other | CN(C=O)C | -15 | 0.333333 | CC(C)CN1CCN(c2ccc(N)cc2)CC1.S=C(n1ccnc1)n1ccnc1>CN(C=O)C>CC(C)CN1CCN(c2ccc(N=C=S)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-73aec980c739465dae1d7432720481ad | O=[N+]([O-])c1ccc(N2CCN(CCCO)CC2)cc1.[N-]=C=S>>OCCCN1CCN(c2ccc(N=C=S)cc2)CC1 | [N+](=O)([O-])C1=CC=C(C=C1)N1CCN(CC1)CCCO.[N-]=C=S>>OCCCN1CCN(CC1)C1=CC=C(C=C1)N=C=S | O=[N+]([O-])[c:12]1[cH:11][cH:10][c:9]([N:8]2[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][CH2:2][OH:1])[CH2:19][CH2:18]2)[cH:17][cH:16]1.[N-:13]=[C:14]=[S:15]>>[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([N:13]=[C:14]=[S:15])[cH:16][cH:17]2)[CH2:18][CH2:19]1 | O=[N+]([O-])c1ccc(N2CCN(CCCO)CC2)cc1.[N-]=C=S | OCCCN1CCN(c2ccc(N=C=S)cc2)CC1 | null | null | null | Functional Group Interconversion | OtherReaction | c2b664bf7684468a37396b968ac0af317a7e2289f2edcfb8b7ab78ab404e94b4 | 305b6f3127a1d497f5798d688e7949ef02b1f99b0e5e183d105619e0875515fa | c1ccc(N2CCNCC2)cc1 | O=[N+](-[O-])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[N-;H0;D1:6]=[C:7]=[S;D1;H0:8]>>[S;D1;H0:8]=[C:7]=[N;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | null | null | This compound was prepared from 4-(4-nitrophenyl)-1-piperazinepropanol (which can be prepared according to the procedure of Loewe and Mieth Arzneim.-Forsch. 1966, 16, 1306–1310) using the hydrogenation and isothiocyanate-forming reactions used in Example 4. MS (ES) MH+=277.
Conditions: See reaction.notes.procedure_deta... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Isothiocyanate | c1ccccc1 | c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1 | Other | null | null | null | O=[N+]([O-])c1ccc(N2CCN(CCCO)CC2)cc1.[N-]=C=S>>OCCCN1CCN(c2ccc(N=C=S)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-604b53f6ab9a40748ebb4ec414303e96 | Nc1ccc(N2CCN(CC3CC3)CC2)cc1.S=C(n1ccnc1)n1ccnc1>>S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1 | C1(CC1)CN1CCN(CC1)C1=CC=C(C=C1)N.C(=S)(N1C=NC=C1)N1C=NC=C1>>N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)CC1CC1 | [NH2:3][c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([CH2:12][CH:13]3[CH2:14][CH2:15]3)[CH2:16][CH2:17]2)[cH:18][cH:19]1.c1cn([C:2](n2ccnc2)=[S:1])cn1>>[S:1]=[C:2]=[N:3][c:4]1[cH:5][cH:6][c:7]([N:8]2[CH2:9][CH2:10][N:11]([CH2:12][CH:13]3[CH2:14][CH2:15]3)[CH2:16][CH2:17]2)[cH:18][cH:19]1 | Nc1ccc(N2CCN(CC3CC3)CC2)cc1.S=C(n1ccnc1)n1ccnc1 | S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | be7cda7c305cb7fe0f9c01bbc607472f3b10db5b9ac4c3f6176bd6d49196c1b0 | b9d004d515d4691c0e9944172fdecaa5dd531c6cfbffee450da8866f92f0f7d4 | c1ccc(N2CCN(CC3CC3)CC2)cc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[S;D1;H0:5]=[C;H0;D3;+0:6](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[S;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | -15 | CELSIUS | 20 | MINUTE | A solution of 4-[4-(cyclopropylmethyl)-1-piperazinyl]benzenamine (3.7 g, 16 mmol) (from Step B above) in N,N-dimethylformamide (50 mL) was added dropwise over 20 min to a cooled (−15° C.) solution of thiocarbonyldiimidazole (2.87 g, 16.1 mmol) (Aldrich) in N,N-dimethylformamide (25 mL). After the addition was complete,... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Thiocarbonyl | Isothiocyanate | c1c[nH]cn1.c1c[nH]cn1 | null | c1ccccc1.C1C[NH]CC[NH]1.C1CC1 | Other | CN(C=O)C | -15 | 0.333333 | Nc1ccc(N2CCN(CC3CC3)CC2)cc1.S=C(n1ccnc1)n1ccnc1>CN(C=O)C>S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-df8740b33601414ebe721ffc9cf8e541 | BrBr.CCc1cccc(C(C)=O)c1>>CCc1cccc(C(=O)CBr)c1 | CCC1=CC=CC(=C1)C(=O)C.BrBr>>BrCC(=O)C1=CC(=CC=C1)CC | Br[Br:11].[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[CH3:10])[cH:12]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[CH2:10][Br:11])[cH:12]1 | BrBr.CCc1cccc(C(C)=O)c1 | CCc1cccc(C(=O)CBr)c1 | null | null | O1CCOCC1 | 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] | 68.1 | [{"value": 68.0, "product": "BrCC(=O)C1=CC(=CC=C1)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.1, "product": "BrCC(=O)C1=CC(=CC=C1)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a stirred solution of 3-ethylacetophenone (Maybridge Chemical Company Ltd.; 1.103 g, 7.44 mmol) in dry 1,4-dioxane (15 mL) was added bromine (383 μL, 7.44 mmol). The solution was stirred at room temperature for 30 min. and then the solvent was removed on a rotary evaporator. The residue was chromatographed on a Foxy... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | O1CCOCC1 | null | 0.5 | BrBr.CCc1cccc(C(C)=O)c1>O1CCOCC1>CCc1cccc(C(=O)CBr)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0ed24783b19a418792f2d568d95728e8 | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.O=C(CBr)c1ccc(Cl)c([N+](=O)[O-])c1>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1 | BrCC(=O)C1=CC(=C(C=C1)Cl)[N+](=O)[O-].N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C.N#CN.CC(C)([O-])C.[K+]>>NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)Cl)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([N:10]=[C:11]=[S:28])[cH:29][cH:30]2)[CH2:31][CH2:32]1.[NH2:12][C:13]#[N:14].Br[CH2:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([Cl:22])[c:23]([N+:24](=[O:25])[O-:26])[cH:27]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][c:13](... | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.O=C(CBr)c1ccc(Cl)c([N+](=O)[O-])c1 | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1 | null | null | O.C(C)#N | Aromatic Heterocycle Formation | OtherReaction | b99ec609035316c2a2b31cbe39b4884eced779d63c233138f1bb7b0b5332bbd9 | f823888efa3dd9a83cac8c606836fbef62e4a8aeb8551af6549e3b12f8a39204 | O=C(c1ccccc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[NH2;D1;+0:7].[S;H0;D1;+0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[s;H0;D2;+0:8]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | 45 | [{"value": 45.0, "product": "NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)Cl)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.3, "product": "NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)Cl)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a mixture of 1-(4-isothiocyanatophenyl)-4-methylpiperazine (of Example 1; 1.0 g, 4.3 mmol) and cyanamide (0.2 g, 4.8 mmol) in acetonitrile (43 mL), a solution of potassium tert-butoxide (43 mL, 0.1 M in tert-BuOH) was added. After 30 minutes at room temperature, 2-bromo-1-(4-chloro-3-nitro-phenyl)ethanone (1.2 g, 4.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ketone.Isothiocyanate | Ketone.Primary amine.Secondary amine | null | c1cscn1 | C1C[NH]CC[NH]1.c1ccccc1.c1cscn1.c1ccccc1 | HBr | O.C(C)#N | null | 0.5 | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.O=C(CBr)c1ccc(Cl)c([N+](=O)[O-])c1>O.C(C)#N>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4444a9b30ad444b689cb68b79a2ae3f2 | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.O=C(CBr)c1ccc2c(c1)OCCO2>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc5c(c4)OCCO5)s3)cc2)CC1 | BrCC(=O)C1=CC2=C(OCCO2)C=C1.N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C.N#CN.CC(C)([O-])C.[K+]>>NC=1N=C(SC1C(=O)C1=CC2=C(OCCO2)C=C1)NC1=CC=C(C=C1)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([N:10]=[C:11]=[S:28])[cH:29][cH:30]2)[CH2:31][CH2:32]1.[NH2:12][C:13]#[N:14].Br[CH2:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23]1)[O:24][CH2:25][CH2:26][O:27]2>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][c:13]([N... | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.O=C(CBr)c1ccc2c(c1)OCCO2 | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc5c(c4)OCCO5)s3)cc2)CC1 | null | null | C(C)(C)(C)O.C(C)#N | Aromatic Heterocycle Formation | OtherReaction | b99ec609035316c2a2b31cbe39b4884eced779d63c233138f1bb7b0b5332bbd9 | f823888efa3dd9a83cac8c606836fbef62e4a8aeb8551af6549e3b12f8a39204 | O=C(c1ccc2c(c1)OCCO2)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[NH2;D1;+0:7].[S;H0;D1;+0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[s;H0;D2;+0:8]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | 66 | [{"value": 66.0, "product": "NC=1N=C(SC1C(=O)C1=CC2=C(OCCO2)C=C1)NC1=CC=C(C=C1)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.0, "product": "NC=1N=C(SC1C(=O)C1=CC2=C(OCCO2)C=C1)NC1=CC=C(C=C1)N1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | tert-Butanol (4 mL) and then 1-(4-isothiocyanatophenyl)-4-methyl piperazine (of Example 1; 219 mg, 1 mmol) were added to a solution of cyanamide (44 mg, 1.05 mmol) (Aldrich) in acetonitrile (5 mL). Potassium t-butoxide (1 M in tert-butanol; 1 mL, 1 mmol) was added and the solution was stirred for 30 min. 2-Bromo-1-(2,3... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ketone.Isothiocyanate | Ketone.Primary amine.Secondary amine | null | c1cscn1 | C1C[NH]CC[NH]1.c1ccccc1.c1cscn1.c1ccc2c(c1)OCCO2 | HBr | C(C)(C)(C)O.C(C)#N | null | 0.5 | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.O=C(CBr)c1ccc2c(c1)OCCO2>C(C)(C)(C)O.C(C)#N>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc5c(c4)OCCO5)s3)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e2adeb5088e848eab7be6471672b965b | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.O=C(CBr)c1ccc2c(c1)OCO2>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc5c(c4)OCO5)s3)cc2)CC1 | N#CN.N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C.O1COC2=C1C=CC(=C2)C(CBr)=O>>NC=1N=C(SC1C(=O)C1=CC2=C(OCO2)C=C1)NC1=CC=C(C=C1)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([N:10]=[C:11]=[S:27])[cH:28][cH:29]2)[CH2:30][CH2:31]1.[NH2:12][C:13]#[N:14].Br[CH2:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23]1)[O:24][CH2:25][O:26]2>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][c:13]([NH2:14])[... | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.O=C(CBr)c1ccc2c(c1)OCO2 | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc5c(c4)OCO5)s3)cc2)CC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b99ec609035316c2a2b31cbe39b4884eced779d63c233138f1bb7b0b5332bbd9 | f823888efa3dd9a83cac8c606836fbef62e4a8aeb8551af6549e3b12f8a39204 | O=C(c1ccc2c(c1)OCO2)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[NH2;D1;+0:7].[S;H0;D1;+0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[s;H0;D2;+0:8]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | 75 | [{"value": 75.0, "product": "NC=1N=C(SC1C(=O)C1=CC2=C(OCO2)C=C1)NC1=CC=C(C=C1)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was prepared in 75% yield from cyanamide (Aldrich), 1-(4-isothiocyanatophenyl)-4-methylpiperazine (of Example 1), and 1-(1,3-benzodioxol-5-yl)-2-bromoethanone (of Example 11) following the procedure used to in Example 24.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ketone.Isothiocyanate | Ketone.Primary amine.Secondary amine | null | c1cscn1 | C1C[NH]CC[NH]1.c1ccccc1.c1cscn1.c1ccc2c(c1)OCO2 | HBr | null | null | null | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.O=C(CBr)c1ccc2c(c1)OCO2>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc5c(c4)OCO5)s3)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b17a0c7b6d284d0a959d2f696bb214cf | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.O=C(CBr)c1ccc(N2CCCC2)cc1>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(N5CCCC5)cc4)s3)cc2)CC1 | BrCC(=O)C1=CC=C(C=C1)N1CCCC1.N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C.N#CN.CC(C)([O-])C.[K+]>>NC=1N=C(SC1C(=O)C1=CC=C(C=C1)N1CCCC1)NC1=CC=C(C=C1)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([N:10]=[C:11]=[S:29])[cH:30][cH:31]2)[CH2:32][CH2:33]1.[NH2:12][C:13]#[N:14].Br[CH2:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([N:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)[cH:27][cH:28]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:1... | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.O=C(CBr)c1ccc(N2CCCC2)cc1 | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(N5CCCC5)cc4)s3)cc2)CC1 | null | null | C(C)(C)(C)O.C(C)#N | Aromatic Heterocycle Formation | OtherReaction | b99ec609035316c2a2b31cbe39b4884eced779d63c233138f1bb7b0b5332bbd9 | f823888efa3dd9a83cac8c606836fbef62e4a8aeb8551af6549e3b12f8a39204 | O=C(c1ccc(N2CCCC2)cc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[NH2;D1;+0:7].[S;H0;D1;+0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[s;H0;D2;+0:8]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | 4 | [{"value": 4.0, "product": "NC=1N=C(SC1C(=O)C1=CC=C(C=C1)N1CCCC1)NC1=CC=C(C=C1)N1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | tert-Butanol (4 mL) and then 1-(4-isothiocyanatophenyl)-4-methyl piperazine (of Example 1; 219 mg, 1 mmol) were added to a solution of cyanamide (44 mg, 1.05 mmol) in acetonitrile (5 mL). Potassium t-butoxide (1 M in tert-butanol; 1 mL, 1 mmol) was added and the solution was stirred for 30 min. 2-Bromo-1-[4-(1-pyrrolid... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ketone.Isothiocyanate | Ketone.Primary amine.Secondary amine | null | c1cscn1 | C1C[NH]CC[NH]1.c1ccccc1.c1cscn1.c1ccccc1.C1CC[NH]C1 | HBr | C(C)(C)(C)O.C(C)#N | null | 0.5 | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.O=C(CBr)c1ccc(N2CCCC2)cc1>C(C)(C)(C)O.C(C)#N>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(N5CCCC5)cc4)s3)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e78d3b5aa11a457f95286fc7827ae285 | CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3nc(N)c(C(=O)c4cccc(F)c4)s3)cc2)CC1>>Nc1nc(Nc2ccc(N3CCNCC3)cc2)sc1C(=O)c1cccc(F)c1 | NC=1N=C(SC1C(C1=CC(=CC=C1)F)=O)NC1=CC=C(C=C1)N1CCN(CC1)C(=O)OC(C)(C)C.C(=O)(C(F)(F)F)O.C(Cl)Cl>>NC=1N=C(SC1C(=O)C1=CC(=CC=C1)F)NC1=CC=C(C=C1)N1CCNCC1 | CC(C)(C)OC(=O)[N:13]1[CH2:12][CH2:11][N:10]([c:9]2[cH:8][cH:7][c:6]([NH:5][c:4]3[n:3][c:2]([NH2:1])[c:19]([C:20](=[O:21])[c:22]4[cH:23][cH:24][cH:25][c:26]([F:27])[cH:28]4)[s:18]3)[cH:17][cH:16]2)[CH2:15][CH2:14]1>>[NH2:1][c:2]1[n:3][c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([N:10]3[CH2:11][CH2:12][NH:13][CH2:14][CH2:15]3)[cH... | CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3nc(N)c(C(=O)c4cccc(F)c4)s3)cc2)CC1 | Nc1nc(Nc2ccc(N3CCNCC3)cc2)sc1C(=O)c1cccc(F)c1 | null | null | null | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(c1ccccc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | 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 | 100.6 | [{"value": 100.0, "product": "NC=1N=C(SC1C(=O)C1=CC(=CC=C1)F)NC1=CC=C(C=C1)N1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.6, "product": "NC=1N=C(SC1C(=O)C1=CC(=CC=C1)F)NC1=CC=C(C=C1)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 4-[4-[[4-amino-5-(3-fluorobenzoyl)-2-thiazolyl]amino]phenyl]1-piperazinec acid, 1,1-dimethylethyl ester (75 mg, 0.15 mmol) (from Step A above) and a solution of TFA/CH2Cl2 (1:1; 1.5 mL) was gently shaken for 1.5 h. The solution was evaporated in vacuo. To the residue was added resin-bound N,N-diisopropylet... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1cscn1.c1ccccc1.C1C[NH]CCN1.c1ccccc1 | HO- | null | null | 8 | CC(C)(C)OC(=O)N1CCN(c2ccc(Nc3nc(N)c(C(=O)c4cccc(F)c4)s3)cc2)CC1>>Nc1nc(Nc2ccc(N3CCNCC3)cc2)sc1C(=O)c1cccc(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-514f448472b6432cb9ba9c7ab9748ad1 | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1.NCCO>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(NCCO)c([N+](=O)[O-])c4)s3)cc2)CC1 | NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)Cl)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C.C(O)CN.C(C)(C)N(C(C)C)CC>>NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)NCCO)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C | Cl[c:21]1[cH:20][cH:19][c:18]([C:16]([c:15]2[c:13]([NH2:14])[n:12][c:11]([NH:10][c:9]3[cH:8][cH:7][c:6]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:35][CH2:34]4)[cH:33][cH:32]3)[s:31]2)=[O:17])[cH:30][c:26]1[N+:27](=[O:28])[O-:29].[NH2:22][CH2:23][CH2:24][OH:25]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:... | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1.NCCO | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(NCCO)c([N+](=O)[O-])c4)s3)cc2)CC1 | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(c1ccccc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[c:2]:[c:3] | 28 | [{"value": 28.0, "product": "NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)NCCO)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.7, "product": "NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)NCCO)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of [4-amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl](4-chloro-3-nitrophenyl)methanone (of Example 15; 0.25 g, 0.53 mmol), ethanolamine (0.13 mL, 2.12 mmol), N,N-diisopropylethylamine (Aldrich) (0.37 mL, 2.12 mmol) in n-butanol (10 mL) was heated at 100° C. overnight. The solvent was evaporated... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | C1C[NH]CC[NH]1.c1ccccc1.c1cscn1.c1ccccc1 | HCl | C(CCC)O | 100 | null | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1.NCCO>C(CCC)O>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(NCCO)c([N+](=O)[O-])c4)s3)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b309a51fb6514b5eb56f5989cdb84e32 | C1CCNC1.CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(N5CCCC5)c([N+](=O)[O-])c4)s3)cc2)CC1 | NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)Cl)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C.N1CCCC1>>NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)N1CCCC1)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C | [NH:22]1[CH2:23][CH2:24][CH2:25][CH2:26]1.Cl[c:21]1[cH:20][cH:19][c:18]([C:16]([c:15]2[c:13]([NH2:14])[n:12][c:11]([NH:10][c:9]3[cH:8][cH:7][c:6]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:36][CH2:35]4)[cH:34][cH:33]3)[s:32]2)=[O:17])[cH:31][c:27]1[N+:28](=[O:29])[O-:30]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8]... | C1CCNC1.CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1 | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(N5CCCC5)c([N+](=O)[O-])c4)s3)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(c1ccc(N2CCCC2)cc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]1-[C:8]-[C:9]-[C:10]-[NH;D2;+0:11]-1>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:7]-[C:8]-[C:9]-[C:10]-1):[c:2]:[c:3] | null | [] | null | null | null | null | This compound was prepared from the compound of Example 15 and pyrrolidine by the procedure used in Example 57. Mass spectrum (ES) MH+=508.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | c1ccccc1.C1CC[NH]C1 | C1C[NH]CC[NH]1.c1ccccc1.c1cscn1.c1ccccc1.C1CC[NH]C1 | HCl | null | null | null | C1CCNC1.CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(N5CCCC5)c([N+](=O)[O-])c4)s3)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e55884b8a1844eb0851cd06728910c98 | C1COCCN1.CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(N5CCOCC5)c([N+](=O)[O-])c4)s3)cc2)CC1 | NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)Cl)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C.N1CCOCC1>>NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)N1CCOCC1)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C | [NH:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1.Cl[c:21]1[cH:20][cH:19][c:18]([C:16]([c:15]2[c:13]([NH2:14])[n:12][c:11]([NH:10][c:9]3[cH:8][cH:7][c:6]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:37][CH2:36]4)[cH:35][cH:34]3)[s:33]2)=[O:17])[cH:32][c:28]1[N+:29](=[O:30])[O-:31]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7]... | C1COCCN1.CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1 | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(N5CCOCC5)c([N+](=O)[O-])c4)s3)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(c1ccc(N2CCOCC2)cc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[#8:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#8:7]-[C:12]-[C:11]-1):[c:2]:[c:3] | null | [] | null | null | null | null | This compound was prepared from the compound of Example 15 and morpholine by the procedure used in Example 57. Mass spectrum (ES) MH+=524.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1cscn1.c1ccccc1.C1COCC[NH]1 | HCl | null | null | null | C1COCCN1.CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(N5CCOCC5)c([N+](=O)[O-])c4)s3)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1525708d3c8442e29f890fe73ad50d45 | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1.COCCN>>COCCNc1ccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)cc1[N+](=O)[O-] | NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)Cl)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C.COCCN>>NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)NCCOC)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C | Cl[c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[c:12]2[s:13][c:14]([NH:15][c:16]3[cH:17][cH:18][c:19]([N:20]4[CH2:21][CH2:22][N:23]([CH3:24])[CH2:25][CH2:26]4)[cH:27][cH:28]3)[n:29][c:30]2[NH2:31])[cH:32][c:33]1[N+:34](=[O:35])[O-:36].[CH3:1][O:2][CH2:3][CH2:4][NH2:5]>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][c:6]1[cH:7][cH:8][c:9](... | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1.COCCN | COCCNc1ccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)cc1[N+](=O)[O-] | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(c1ccccc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:9]-[C:8]-[C:7]):[c:2]:[c:3] | null | [] | null | null | null | null | This compound was prepared from the compound of Example 15 and 2-methoxyethanamine (Aldrich) by the procedure used in Example 57. Mass spectrum (ES) MH+=512.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cscn1.c1ccccc1.C1C[NH]CC[NH]1 | HCl | null | null | null | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1.COCCN>>COCCNc1ccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)cc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d7b06ea0f2724bfb9e297e97cd7e3e58 | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1.OCC1CCCNC1>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(N5CCCC(CO)C5)c([N+](=O)[O-])c4)s3)cc2)CC1 | NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)Cl)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C.N1CC(CCC1)CO>>NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)N1CC(CCC1)CO)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C | Cl[c:21]1[cH:20][cH:19][c:18]([C:16]([c:15]2[c:13]([NH2:14])[n:12][c:11]([NH:10][c:9]3[cH:8][cH:7][c:6]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:39][CH2:38]4)[cH:37][cH:36]3)[s:35]2)=[O:17])[cH:34][c:30]1[N+:31](=[O:32])[O-:33].[NH:22]1[CH2:23][CH2:24][CH2:25][CH:26]([CH2:27][OH:28])[CH2:29]1>>[CH3:1][N:2]1[CH2:3][CH2:4]... | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1.OCC1CCCNC1 | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(N5CCCC(CO)C5)c([N+](=O)[O-])c4)s3)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(c1ccc(N2CCCCC2)cc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11]):[c:2]:[c:3] | null | [] | null | null | null | null | This compound was prepared from the compound of Example 15 and racemic 3-piperidinemethanol (Aldrich) by the procedure used in Example 57. Mass spectrum (ES) MH+=552.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNCC1 | c1ccccc1.C1CC[NH]CC1 | C1C[NH]CC[NH]1.c1ccccc1.c1cscn1.c1ccccc1.C1CC[NH]CC1 | HCl | null | null | null | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1.OCC1CCCNC1>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(N5CCCC(CO)C5)c([N+](=O)[O-])c4)s3)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f71ea8aaf3d74f99a567d56fac4f7b4d | CC1CCCN1.CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1>>CC1CCCN1c1ccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)cc1[N+](=O)[O-] | NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)Cl)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C.CC1NCCC1>>NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)N1C(CCC1)C)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C | [CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][NH:6]1.Cl[c:7]1[cH:8][cH:9][c:10]([C:11](=[O:12])[c:13]2[s:14][c:15]([NH:16][c:17]3[cH:18][cH:19][c:20]([N:21]4[CH2:22][CH2:23][N:24]([CH3:25])[CH2:26][CH2:27]4)[cH:28][cH:29]3)[n:30][c:31]2[NH2:32])[cH:33][c:34]1[N+:35](=[O:36])[O-:37]>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]1[c:7]... | CC1CCCN1.CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1 | CC1CCCN1c1ccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)cc1[N+](=O)[O-] | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(c1ccc(N2CCCC2)cc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C;D1;H3:7]-[C:8]1-[C:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[C:9]-[C:8]-1-[C;D1;H3:7]):[c:2]:[c:3] | null | [] | null | null | null | null | This compound was prepared from the compound of Example 15 and racemic 2-methylpyrrolidine (Alfa Aesar) by the procedure used in Example 57. Mass spectrum (ES) MH+=522.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | C1CC[NH]C1.c1ccccc1 | C1CC[NH]C1.c1ccccc1.c1cscn1.c1ccccc1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC1CCCN1.CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1>>CC1CCCN1c1ccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)cc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bf0a53130d38412282e165d28ddfe4be | CC(C)C[C@@H](N)CO.CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1>>CC(C)C[C@H](CO)Nc1ccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)cc1[N+](=O)[O-] | NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)Cl)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C.N[C@@H](CO)CC(C)C>>NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)N[C@H](CC(C)C)CO)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C | [CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([CH2:6][OH:7])[NH2:8].Cl[c:9]1[cH:10][cH:11][c:12]([C:13](=[O:14])[c:15]2[s:16][c:17]([NH:18][c:19]3[cH:20][cH:21][c:22]([N:23]4[CH2:24][CH2:25][N:26]([CH3:27])[CH2:28][CH2:29]4)[cH:30][cH:31]3)[n:32][c:33]2[NH2:34])[cH:35][c:36]1[N+:37](=[O:38])[O-:39]>>[CH3:1][CH:2]([CH3:3])[CH2:4... | CC(C)C[C@@H](N)CO.CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1 | CC(C)C[C@H](CO)Nc1ccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)cc1[N+](=O)[O-] | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | da9dae6a655c4bd18887b692f91621e77027436294d6e1fc7be7295afb364796 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(c1ccccc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8](-[C:9])-[NH2;D1;+0:10]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:10]-[C:8](-[C:7])-[C:9]):[c:2]:[c:3] | null | [] | null | null | null | null | This compound was prepared from the compound of Example 15 and (R)-2-amino-4-methyl-1-pentanol (Aldrich) by the procedure used in Example 57. Mass spectrum (ES) MH+=554.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1cscn1.c1ccccc1.C1C[NH]CC[NH]1 | HCl | null | null | null | CC(C)C[C@@H](N)CO.CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1>>CC(C)C[C@H](CO)Nc1ccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)cc1[N+](=O)[O-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a190f012b2de44119320ad4ef6789f10 | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1.OC1CCNCC1>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(N5CCC(O)CC5)c([N+](=O)[O-])c4)s3)cc2)CC1 | NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)Cl)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C.N1CCC(CC1)O>>NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)N1CCC(CC1)O)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C | Cl[c:21]1[cH:20][cH:19][c:18]([C:16]([c:15]2[c:13]([NH2:14])[n:12][c:11]([NH:10][c:9]3[cH:8][cH:7][c:6]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:38][CH2:37]4)[cH:36][cH:35]3)[s:34]2)=[O:17])[cH:33][c:29]1[N+:30](=[O:31])[O-:32].[NH:22]1[CH2:23][CH2:24][CH:25]([OH:26])[CH2:27][CH2:28]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c... | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1.OC1CCNCC1 | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(N5CCC(O)CC5)c([N+](=O)[O-])c4)s3)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ad5ec9c4592e4dee5877fc4f1309a503a378773e18ebc21adf780b709f6e28c5 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(c1ccc(N2CCCCC2)cc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[N;H0;D3;+0:9](-[C:8]-[C:7])-[C:10]-[C:11]):[c:2]:[c:3] | null | [] | null | null | null | null | This compound was prepared from the compound of Example 15 and 4-piperidinol (Aldrich) by the procedure used in Example 57. Mass spectrum (ES) MH+=538.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CCNCC1 | c1ccccc1.C1CC[NH]CC1 | C1C[NH]CC[NH]1.c1ccccc1.c1cscn1.c1ccccc1.C1CC[NH]CC1 | HCl | null | null | null | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(Cl)c([N+](=O)[O-])c4)s3)cc2)CC1.OC1CCNCC1>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4ccc(N5CCC(O)CC5)c([N+](=O)[O-])c4)s3)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e22344accb1d4910a848b743bfa211d1 | CC(C)C[C@H](CO)Nc1ccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)cc1[N+](=O)[O-]>>CC(C)C[C@H](CO)Nc1ccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)cc1N | NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)N[C@H](CC(C)C)CO)[N+](=O)[O-])NC1=CC=C(C=C1)N1CCN(CC1)C.NN.CC(C)O>>NC=1C=C(C=CC1N[C@H](CC(C)C)CO)C(=O)C1=C(N=C(S1)NC1=CC=C(C=C1)N1CCN(CC1)C)N | O=[N+:37]([O-])[c:36]1[c:9]([NH:8][C@H:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:6][OH:7])[cH:10][cH:11][c:12]([C:13](=[O:14])[c:15]2[s:16][c:17]([NH:18][c:19]3[cH:20][cH:21][c:22]([N:23]4[CH2:24][CH2:25][N:26]([CH3:27])[CH2:28][CH2:29]4)[cH:30][cH:31]3)[n:32][c:33]2[NH2:34])[cH:35]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][C@H:5]([... | CC(C)C[C@H](CO)Nc1ccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)cc1[N+](=O)[O-] | CC(C)C[C@H](CO)Nc1ccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)cc1N | null | [Pd] | ClCCl.CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 57.3 | [{"value": 53.0, "product": "NC=1C=C(C=CC1N[C@H](CC(C)C)CO)C(=O)C1=C(N=C(S1)NC1=CC=C(C=C1)N1CCN(CC1)C)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.3, "product": "NC=1C=C(C=CC1N[C@H](CC(C)C)CO)C(=O)C1=C(N=C(S1)NC1=CC=C(C=C1)N1CCN(CC1)C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (R)-[4-amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl][3-nitro-4-[[1-(hydroxymethyl)-3-methylbutyl]amino]phenyl]methanone (of Example 63; 30 mg, 0.05 mmol), NH2NH2 (0.5 mL), 10% Pd/C (5 mg), and 2-propanol (2 mL) was heated at reflux for 1 h. The mixture was filtered through a Celite™ pad a... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1cscn1.c1ccccc1.C1C[NH]CC[NH]1 | Other | [Pd].ClCCl.CO | null | null | CC(C)C[C@H](CO)Nc1ccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)cc1[N+](=O)[O-]>[Pd].ClCCl.CO>CC(C)C[C@H](CO)Nc1ccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)cc1N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-84efb16b6cff4ea9853c2e13e6553a50 | O=P(O)(O)O>>O=P(O)(O)O | NC=1N=C(SC1C(=O)C1=CC(=CC=C1)OC)NC1=CC=C(C=C1)N1CCN(CC1)C(C)C.P(O)(O)(O)=O>>P(O)(O)(O)=O.NC=1N=C(SC1C(=O)C1=CC(=CC=C1)OC)NC1=CC=C(C=C1)N1CCN(CC1)C(C)C | [O:33]=[P:34]([OH:35])([OH:36])[OH:37]>>[O:33]=[P:34]([OH:35])([OH:36])[OH:37] | O=P(O)(O)O | O=P(O)(O)O | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | A solution of {4-amino-2-[4-(4-isopropyl-piperazin-1-yl)-phenylamino]-thiazol-5-yl}-(3-methoxy-phenyl)-methanone (of Example 43; 113 mg, 0.25 mmol) was dissolved in hot ethanol (10 ml) and to this was added 25 mg of phosphoric acid in ethanol (1 ml). This was cooled and crystals were collected and dried to furnish {4-A... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | C(C)O | null | null | O=P(O)(O)O>C(C)O>O=P(O)(O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eeb6facdc8e0446389e7e7456b4ead4b | CN1CCN(c2ccc(N=C=S)cc2)CC1.CSc1cccc(C(=O)CBr)c1.N#CN>>CSc1cccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)c1 | BrCC(=O)C1=CC(=CC=C1)SC.N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C.N#CN.CC(C)([O-])C.[K+]>>NC=1N=C(SC1C(=O)C1=CC(=CC=C1)SC)NC1=CC=C(C=C1)N1CCN(CC1)C | [S:11]=[C:12]=[N:13][c:14]1[cH:15][cH:16][c:17]([N:18]2[CH2:19][CH2:20][N:21]([CH3:22])[CH2:23][CH2:24]2)[cH:25][cH:26]1.Br[CH2:10][C:8]([c:7]1[cH:6][cH:5][cH:4][c:3]([S:2][CH3:1])[cH:30]1)=[O:9].[NH2:27][C:28]#[N:29]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[c:10]2[s:11][c:12]([NH:13][c:14]3[cH:15][cH:1... | CN1CCN(c2ccc(N=C=S)cc2)CC1.CSc1cccc(C(=O)CBr)c1.N#CN | CSc1cccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)c1 | null | null | C(C)(C)(C)O.C(C)(=O)OCC.C(C)#N | Aromatic Heterocycle Formation | OtherReaction | b99ec609035316c2a2b31cbe39b4884eced779d63c233138f1bb7b0b5332bbd9 | f823888efa3dd9a83cac8c606836fbef62e4a8aeb8551af6549e3b12f8a39204 | O=C(c1ccccc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[NH2;D1;+0:7].[S;H0;D1;+0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[s;H0;D2;+0:8]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | 50 | [{"value": 50.0, "product": "NC=1N=C(SC1C(=O)C1=CC(=CC=C1)SC)NC1=CC=C(C=C1)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a mixture of 1-(4-isothiocyanatophenyl)-4-methylpiperazine (of Example 1; 0.466 g, 2.0 mmol) and cyanamide (0.088 g, 2.1 mmol) in acetonitrile (3 mL) and t-butanol (5 ml), a solution of potassium tert-butoxide (2.0 mL, 1.0 M in tert-BuOH) was added. After 30 minutes at room temperature, 2-bromo-1-(3-methylsulfanyl-p... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ketone.Isothiocyanate | Ketone.Primary amine.Secondary amine | null | c1cscn1 | c1ccccc1.c1cscn1.c1ccccc1.C1C[NH]CC[NH]1 | HBr | C(C)(C)(C)O.C(C)(=O)OCC.C(C)#N | null | 0.5 | CN1CCN(c2ccc(N=C=S)cc2)CC1.CSc1cccc(C(=O)CBr)c1.N#CN>C(C)(C)(C)O.C(C)(=O)OCC.C(C)#N>CSc1cccc(C(=O)c2sc(Nc3ccc(N4CCN(C)CC4)cc3)nc2N)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3c6803e0976a49bba12682bb51f30c25 | CC(C)N1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.N#Cc1cccc(C(=O)CBr)c1>>CC(C)N1CCN(c2ccc(Nc3nc(N)c(C(=O)c4cccc(C#N)c4)s3)cc2)CC1 | N#CN.N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C(C)C.C(#N)C=1C=C(C(CBr)=O)C=CC1>>NC=1N=C(SC1C(=O)C=1C=C(C#N)C=CC1)NC1=CC=C(C=C1)N1CCN(CC1)C(C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([N:12]=[C:13]=[S:28])[cH:29][cH:30]2)[CH2:31][CH2:32]1.[NH2:14][C:15]#[N:16].Br[CH2:17][C:18](=[O:19])[c:20]1[cH:21][cH:22][cH:23][c:24]([C:25]#[N:26])[cH:27]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][N:7]([c:8]2[cH:9][cH:10][c:11]([NH:12][c:1... | CC(C)N1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.N#Cc1cccc(C(=O)CBr)c1 | CC(C)N1CCN(c2ccc(Nc3nc(N)c(C(=O)c4cccc(C#N)c4)s3)cc2)CC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b99ec609035316c2a2b31cbe39b4884eced779d63c233138f1bb7b0b5332bbd9 | f823888efa3dd9a83cac8c606836fbef62e4a8aeb8551af6549e3b12f8a39204 | O=C(c1ccccc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[NH2;D1;+0:7].[S;H0;D1;+0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[s;H0;D2;+0:8]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | This compound was prepared from cyanamide, 1-(4-isothiocyanatophenyl)-4-isopropypiperazine (of Example 3) and 3-cyanophenacyl bromide (Maybridge Chemical Co. Ltd.) following the procedure used in Example 24. Mass spectrum (ES) MH+=447.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ketone.Isothiocyanate | Ketone.Primary amine.Secondary amine | null | c1cscn1 | C1C[NH]CC[NH]1.c1ccccc1.c1cscn1.c1ccccc1 | HBr | null | null | null | CC(C)N1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.N#Cc1cccc(C(=O)CBr)c1>>CC(C)N1CCN(c2ccc(Nc3nc(N)c(C(=O)c4cccc(C#N)c4)s3)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-613fa06c3fcd4a528f837a7497987e54 | N#CN.O=C(CBr)c1cccc(OC(F)F)c1.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1>>Nc1nc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)sc1C(=O)c1cccc(OC(F)F)c1 | N#CN.N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)CC1CC1.BrCC(=O)C1=CC(=CC=C1)OC(F)F>>NC=1N=C(SC1C(=O)C1=CC(=CC=C1)OC(F)F)NC1=CC=C(C=C1)N1CCN(CC1)CC1CC1 | [N:1]#[C:2][NH2:3].Br[CH2:23][C:24](=[O:25])[c:26]1[cH:27][cH:28][cH:29][c:30]([O:31][CH:32]([F:33])[F:34])[cH:35]1.[C:4](=[N:5][c:6]1[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][N:13]([CH2:14][CH:15]3[CH2:16][CH2:17]3)[CH2:18][CH2:19]2)[cH:20][cH:21]1)=[S:22]>>[NH2:1][c:2]1[n:3][c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([N:10]3... | N#CN.O=C(CBr)c1cccc(OC(F)F)c1.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1 | Nc1nc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)sc1C(=O)c1cccc(OC(F)F)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b99ec609035316c2a2b31cbe39b4884eced779d63c233138f1bb7b0b5332bbd9 | f823888efa3dd9a83cac8c606836fbef62e4a8aeb8551af6549e3b12f8a39204 | O=C(c1ccccc1)c1cnc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[NH2;D1;+0:7].[S;H0;D1;+0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[s;H0;D2;+0:8]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | This compound was prepared from cyanamide, 1-(4-isothiocyanatophenyl)-4-cyclopropylmethylpiperazine (of Example 14G) and 2-bromo-1-(3-difluoro-methoxyphenyl)ethanone (of Example 14L) following the procedure used in Example 24. Mass spectrum (ES) MH+=500.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ketone.Isothiocyanate | Ketone.Primary amine.Secondary amine | null | c1cscn1 | c1cscn1.c1ccccc1.C1C[NH]CC[NH]1.C1CC1.c1ccccc1 | HBr | null | null | null | N#CN.O=C(CBr)c1cccc(OC(F)F)c1.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1>>Nc1nc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)sc1C(=O)c1cccc(OC(F)F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-85ee76f1be514947a55c08761ca008f0 | COc1cccc(C(=O)CBr)c1.N#CN.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1>>COc1cccc(C(=O)c2sc(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)nc2N)c1 | N#CN.N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)CC1CC1.BrCC(=O)C1=CC(=CC=C1)OC>>NC=1N=C(SC1C(=O)C1=CC(=CC=C1)OC)NC1=CC=C(C=C1)N1CCN(CC1)CC1CC1 | Br[CH2:10][C:8]([c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[cH:33]1)=[O:9].[NH2:30][C:31]#[N:32].[S:11]=[C:12]=[N:13][c:14]1[cH:15][cH:16][c:17]([N:18]2[CH2:19][CH2:20][N:21]([CH2:22][CH:23]3[CH2:24][CH2:25]3)[CH2:26][CH2:27]2)[cH:28][cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[c:10]2[s:11][c:12]([... | COc1cccc(C(=O)CBr)c1.N#CN.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1 | COc1cccc(C(=O)c2sc(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)nc2N)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b99ec609035316c2a2b31cbe39b4884eced779d63c233138f1bb7b0b5332bbd9 | f823888efa3dd9a83cac8c606836fbef62e4a8aeb8551af6549e3b12f8a39204 | O=C(c1ccccc1)c1cnc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[NH2;D1;+0:7].[S;H0;D1;+0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[s;H0;D2;+0:8]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | This compound was prepared from cyanamide, 1-(4-isothiocyanatophenyl)-4-cyclopropylmethylpiperazine (of Example 14G) and 2-bromo-1-(3-methoxyphenyl)ethanone (Aldrich) following the procedure used in Example 24 Mass spectrum (ES) MH+=464.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ketone.Isothiocyanate | Ketone.Primary amine.Secondary amine | null | c1cscn1 | c1ccccc1.c1cscn1.c1ccccc1.C1C[NH]CC[NH]1.C1CC1 | HBr | null | null | null | COc1cccc(C(=O)CBr)c1.N#CN.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1>>COc1cccc(C(=O)c2sc(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)nc2N)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8d916d1a8d734bca8f579d63c504873f | N#CN.O=C(CBr)c1ccc2c(c1)OCO2.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1>>Nc1nc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)sc1C(=O)c1ccc2c(c1)OCO2 | N#CN.N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)CC1CC1.O1COC2=C1C=CC(=C2)C(CBr)=O>>NC=1N=C(SC1C(=O)C1=CC2=C(OCO2)C=C1)NC1=CC=C(C=C1)N1CCN(CC1)CC1CC1 | [N:1]#[C:2][NH2:3].Br[CH2:23][C:24](=[O:25])[c:26]1[cH:27][cH:28][c:29]2[c:30]([cH:31]1)[O:32][CH2:33][O:34]2.[C:4](=[N:5][c:6]1[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][N:13]([CH2:14][CH:15]3[CH2:16][CH2:17]3)[CH2:18][CH2:19]2)[cH:20][cH:21]1)=[S:22]>>[NH2:1][c:2]1[n:3][c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([N:10]3[CH2:1... | N#CN.O=C(CBr)c1ccc2c(c1)OCO2.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1 | Nc1nc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)sc1C(=O)c1ccc2c(c1)OCO2 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b99ec609035316c2a2b31cbe39b4884eced779d63c233138f1bb7b0b5332bbd9 | f823888efa3dd9a83cac8c606836fbef62e4a8aeb8551af6549e3b12f8a39204 | O=C(c1ccc2c(c1)OCO2)c1cnc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[NH2;D1;+0:7].[S;H0;D1;+0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[s;H0;D2;+0:8]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | This compound was prepared from cyanamide, 1-(4-isothiocyanatophenyl)-4-cyclopropylmethylpiperazine (of Example 14G) and 2-bromo-[(benzo[1,3]dioxol-5-yl)ethanone (of Example 11) following the procedure used in Example 24 Mass spectrum (ES) MH+=478.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ketone.Isothiocyanate | Ketone.Primary amine.Secondary amine | null | c1cscn1 | c1cscn1.c1ccccc1.C1C[NH]CC[NH]1.C1CC1.c1ccc2c(c1)OCO2 | HBr | null | null | null | N#CN.O=C(CBr)c1ccc2c(c1)OCO2.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1>>Nc1nc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)sc1C(=O)c1ccc2c(c1)OCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d81c27ecaf974a728c8d06da8118a081 | N#CN.O=C(CBr)c1ccc2c(c1)OCCO2.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1>>Nc1nc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)sc1C(=O)c1ccc2c(c1)OCCO2 | N#CN.N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)CC1CC1.BrCC(=O)C1=CC2=C(OCCO2)C=C1>>NC=1N=C(SC1C(=O)C1=CC2=C(OCCO2)C=C1)NC1=CC=C(C=C1)N1CCN(CC1)CC1CC1 | [N:1]#[C:2][NH2:3].Br[CH2:23][C:24](=[O:25])[c:26]1[cH:27][cH:28][c:29]2[c:30]([cH:31]1)[O:32][CH2:33][CH2:34][O:35]2.[C:4](=[N:5][c:6]1[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][N:13]([CH2:14][CH:15]3[CH2:16][CH2:17]3)[CH2:18][CH2:19]2)[cH:20][cH:21]1)=[S:22]>>[NH2:1][c:2]1[n:3][c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([N:10... | N#CN.O=C(CBr)c1ccc2c(c1)OCCO2.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1 | Nc1nc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)sc1C(=O)c1ccc2c(c1)OCCO2 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b99ec609035316c2a2b31cbe39b4884eced779d63c233138f1bb7b0b5332bbd9 | f823888efa3dd9a83cac8c606836fbef62e4a8aeb8551af6549e3b12f8a39204 | O=C(c1ccc2c(c1)OCCO2)c1cnc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[NH2;D1;+0:7].[S;H0;D1;+0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[s;H0;D2;+0:8]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | This compound was prepared from cyanamide, 1-(4-isothiocyanatophenyl)-4-cyclopropylmethylpiperazine (of Example 14G) and 2-bromo-1-(2,3-dihydro-benzo[1,4]dioxin-6-yl)ethanone (Maybridge Chemical Company Ltd.) following the procedure used in Example 24. Mass spectrum (ES) MH+=492.
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ketone.Isothiocyanate | Ketone.Primary amine.Secondary amine | null | c1cscn1 | c1cscn1.c1ccccc1.C1C[NH]CC[NH]1.C1CC1.c1ccc2c(c1)OCCO2 | HBr | null | null | null | N#CN.O=C(CBr)c1ccc2c(c1)OCCO2.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1>>Nc1nc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)sc1C(=O)c1ccc2c(c1)OCCO2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-00c077eb05ac42d3b480fa4c391efc38 | N#CN.O=C(CBr)c1ccc(O)c(F)c1.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1>>Nc1nc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)sc1C(=O)c1ccc(O)c(F)c1 | N#CN.N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)CC1CC1.BrCC(=O)C1=CC(=C(C=C1)O)F>>NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)O)F)NC1=CC=C(C=C1)N1CCN(CC1)CC1CC1 | [N:1]#[C:2][NH2:3].Br[CH2:23][C:24](=[O:25])[c:26]1[cH:27][cH:28][c:29]([OH:30])[c:31]([F:32])[cH:33]1.[C:4](=[N:5][c:6]1[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][N:13]([CH2:14][CH:15]3[CH2:16][CH2:17]3)[CH2:18][CH2:19]2)[cH:20][cH:21]1)=[S:22]>>[NH2:1][c:2]1[n:3][c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([N:10]3[CH2:11][CH2:... | N#CN.O=C(CBr)c1ccc(O)c(F)c1.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1 | Nc1nc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)sc1C(=O)c1ccc(O)c(F)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b99ec609035316c2a2b31cbe39b4884eced779d63c233138f1bb7b0b5332bbd9 | f823888efa3dd9a83cac8c606836fbef62e4a8aeb8551af6549e3b12f8a39204 | O=C(c1ccccc1)c1cnc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[NH2;D1;+0:7].[S;H0;D1;+0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[s;H0;D2;+0:8]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | This compound was prepared from cyanamide, 1-(4-isothiocyanatophenyl)-4-cyclopropylmethylpiperazine (of Example 14G) and 2-bromo-1-(3-fluoro-4-hydroxyphenyl)ethanone (of Example 14M) following the procedure used in Example 24. Mass spectrum (ES) MH+=468.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ketone.Isothiocyanate | Ketone.Primary amine.Secondary amine | null | c1cscn1 | c1cscn1.c1ccccc1.C1C[NH]CC[NH]1.C1CC1.c1ccccc1 | HBr | null | null | null | N#CN.O=C(CBr)c1ccc(O)c(F)c1.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1>>Nc1nc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)sc1C(=O)c1ccc(O)c(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3cb452d5092d4ae89fecc9ecd25459f7 | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.O=C(CBr)c1cccc(OC(F)F)c1>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4cccc(OC(F)F)c4)s3)cc2)CC1 | N#CN.N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C.BrCC(=O)C1=CC(=CC=C1)OC(F)F>>NC=1N=C(SC1C(=O)C1=CC(=CC=C1)OC(F)F)NC1=CC=C(C=C1)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([N:10]=[C:11]=[S:28])[cH:29][cH:30]2)[CH2:31][CH2:32]1.[NH2:12][C:13]#[N:14].Br[CH2:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21][c:22]([O:23][CH:24]([F:25])[F:26])[cH:27]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][c:13]([NH2... | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.O=C(CBr)c1cccc(OC(F)F)c1 | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4cccc(OC(F)F)c4)s3)cc2)CC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b99ec609035316c2a2b31cbe39b4884eced779d63c233138f1bb7b0b5332bbd9 | f823888efa3dd9a83cac8c606836fbef62e4a8aeb8551af6549e3b12f8a39204 | O=C(c1ccccc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[NH2;D1;+0:7].[S;H0;D1;+0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[s;H0;D2;+0:8]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | This compound was prepared from cyanamide, 1-(4-isothiocyanatophenyl)-4-methylpiperazine (of Example 1) and 2-bromo-1-(3-difluoromethoxy-phenyl)ethanone (of Example 14L) following the procedure used in Example 24. Mass spectrum (ES) MH+=460.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ketone.Isothiocyanate | Ketone.Primary amine.Secondary amine | null | c1cscn1 | C1C[NH]CC[NH]1.c1ccccc1.c1cscn1.c1ccccc1 | HBr | null | null | null | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.O=C(CBr)c1cccc(OC(F)F)c1>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4cccc(OC(F)F)c4)s3)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-04d595ef5af24223bfc0b9fd7caf593a | N#CN.O=C(CBr)c1cccc(F)c1.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1>>Nc1nc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)sc1C(=O)c1cccc(F)c1 | N#CN.N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)CC1CC1.BrCC(=O)C1=CC(=CC=C1)F>>NC=1N=C(SC1C(=O)C1=CC(=CC=C1)F)NC1=CC=C(C=C1)N1CCN(CC1)CC1CC1 | [N:1]#[C:2][NH2:3].Br[CH2:23][C:24](=[O:25])[c:26]1[cH:27][cH:28][cH:29][c:30]([F:31])[cH:32]1.[C:4](=[N:5][c:6]1[cH:7][cH:8][c:9]([N:10]2[CH2:11][CH2:12][N:13]([CH2:14][CH:15]3[CH2:16][CH2:17]3)[CH2:18][CH2:19]2)[cH:20][cH:21]1)=[S:22]>>[NH2:1][c:2]1[n:3][c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([N:10]3[CH2:11][CH2:12][N:13... | N#CN.O=C(CBr)c1cccc(F)c1.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1 | Nc1nc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)sc1C(=O)c1cccc(F)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b99ec609035316c2a2b31cbe39b4884eced779d63c233138f1bb7b0b5332bbd9 | f823888efa3dd9a83cac8c606836fbef62e4a8aeb8551af6549e3b12f8a39204 | O=C(c1ccccc1)c1cnc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[NH2;D1;+0:7].[S;H0;D1;+0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[s;H0;D2;+0:8]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | This compound was prepared from cyanamide, 1-(4-isothiocyanatphenyl)-4-cyclopropylmethylpiperazine (of Example 14G) and 2-bromo-1-(3-fluorophenyl)ethanone (Aldrich) following the procedure used in Example 24 Mass spectrum (ES) MH+=452.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ketone.Isothiocyanate | Ketone.Primary amine.Secondary amine | null | c1cscn1 | c1cscn1.c1ccccc1.C1C[NH]CC[NH]1.C1CC1.c1ccccc1 | HBr | null | null | null | N#CN.O=C(CBr)c1cccc(F)c1.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1>>Nc1nc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)sc1C(=O)c1cccc(F)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b346d66b2c9c44adaf6cbc93142ddcf2 | COc1ccc(C(=O)CBr)cc1F.N#CN.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1>>COc1ccc(C(=O)c2sc(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)nc2N)cc1F | N#CN.N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)CC1CC1.BrCC(=O)C1=CC(=C(C=C1)OC)F>>NC=1N=C(SC1C(=O)C1=CC(=C(C=C1)OC)F)NC1=CC=C(C=C1)N1CCN(CC1)CC1CC1 | Br[CH2:9][C:7]([c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:33]([F:34])[cH:32]1)=[O:8].[NH2:29][C:30]#[N:31].[S:10]=[C:11]=[N:12][c:13]1[cH:14][cH:15][c:16]([N:17]2[CH2:18][CH2:19][N:20]([CH2:21][CH:22]3[CH2:23][CH2:24]3)[CH2:25][CH2:26]2)[cH:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[s:10][c:11]([... | COc1ccc(C(=O)CBr)cc1F.N#CN.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1 | COc1ccc(C(=O)c2sc(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)nc2N)cc1F | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b99ec609035316c2a2b31cbe39b4884eced779d63c233138f1bb7b0b5332bbd9 | f823888efa3dd9a83cac8c606836fbef62e4a8aeb8551af6549e3b12f8a39204 | O=C(c1ccccc1)c1cnc(Nc2ccc(N3CCN(CC4CC4)CC3)cc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[NH2;D1;+0:7].[S;H0;D1;+0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[s;H0;D2;+0:8]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | This compound was prepared from cyanamide, 1-(4-isothiocyanatophenyl)-4-cyclopropylmethylpiperazine (of Example 14G) and 2-bromo-1-(3-fluoro-4-methoxyphenyl)ethanone (of Example 13) following the procedure used in Example 24. Mass spectrum (ES) MH+=482.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ketone.Isothiocyanate | Ketone.Primary amine.Secondary amine | null | c1cscn1 | c1ccccc1.c1cscn1.c1ccccc1.C1C[NH]CC[NH]1.C1CC1 | HBr | null | null | null | COc1ccc(C(=O)CBr)cc1F.N#CN.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1>>COc1ccc(C(=O)c2sc(Nc3ccc(N4CCN(CC5CC5)CC4)cc3)nc2N)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-25d1fdad70a740bb8250dd9d84aad07f | N#CN.O=C(CBr)c1cccc(O)c1.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4cccc(O)c4)s3)cc2)CC1 | N#CN.N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)CC1CC1.BrCC(=O)C1=CC(=CC=C1)O>>NC=1N=C(SC1C(=O)C1=CC(=CC=C1)O)NC1=CC=C(C=C1)N1CCN(CC1)C | [NH2:12][C:13]#[N:14].Br[CH2:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21][c:22]([OH:23])[cH:24]1.C1CC1[CH2:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([N:10]=[C:11]=[S:25])[cH:26][cH:27]2)[CH2:28][CH2:29]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][c:13]([NH2:14])[c:15]([C:... | N#CN.O=C(CBr)c1cccc(O)c1.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1 | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4cccc(O)c4)s3)cc2)CC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | afe22251e31860d151b8b251b14d1e16fb67bd2cf918f23bb8a875f5cdf1a9c0 | f823888efa3dd9a83cac8c606836fbef62e4a8aeb8551af6549e3b12f8a39204 | O=C(c1ccccc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[C:5]-[#7:6](-[CH2;D2;+0:7]-C1-C-C-1)-[C:8].[S;H0;D1;+0:9]=[C;H0;D2;+0:10]=[N;H0;D2;+0:11]-[c:12](:[c:13]):[c:14].[N;H0;D1;+0:15]#[C;H0;D2;+0:16]-[NH2;D1;+0:17]>>[C:5]-[#7:6](-[CH3;D1;+0:7])-[C:8].[NH2;D1;+0:15]-[c;H0;D3;+0:16]1:[n;H0;D2;+0:17]:[c;H0;D3;+0:10](-[NH;D2;+0:11]-[... | null | [] | null | null | null | null | This compound was prepared from cyanamide, 1-(4-isothiocyanatophenyl)-4-cyclopropylmethylpiperazine (of Example 1) and 2-bromo-1-(3-hydroxyphenyl)ethanone (of Example 14N) following the procedure used in Example 24. Mass spectrum (ES) MH+=410.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ketone.Isothiocyanate | Ketone.Primary amine.Secondary amine | C1CC1 | c1cscn1 | C1C[NH]CC[NH]1.c1ccccc1.c1cscn1.c1ccccc1 | HBr | null | null | null | N#CN.O=C(CBr)c1cccc(O)c1.S=C=Nc1ccc(N2CCN(CC3CC3)CC2)cc1>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4cccc(O)c4)s3)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c603c17d1e644a2c978edd1e4dbbd2c6 | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.N#Cc1cccc(C(=O)CBr)c1>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4cccc(C#N)c4)s3)cc2)CC1 | N#CN.N(=C=S)C1=CC=C(C=C1)N1CCN(CC1)C.C(#N)C=1C=C(C(CBr)=O)C=CC1>>NC=1N=C(SC1C(=O)C=1C=C(C#N)C=CC1)NC1=CC=C(C=C1)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([N:10]=[C:11]=[S:26])[cH:27][cH:28]2)[CH2:29][CH2:30]1.[NH2:12][C:13]#[N:14].Br[CH2:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][cH:21][c:22]([C:23]#[N:24])[cH:25]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][c:13]([NH2:14])[c:15]([C... | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.N#Cc1cccc(C(=O)CBr)c1 | CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4cccc(C#N)c4)s3)cc2)CC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b99ec609035316c2a2b31cbe39b4884eced779d63c233138f1bb7b0b5332bbd9 | f823888efa3dd9a83cac8c606836fbef62e4a8aeb8551af6549e3b12f8a39204 | O=C(c1ccccc1)c1cnc(Nc2ccc(N3CCNCC3)cc2)s1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[N;H0;D1;+0:5]#[C;H0;D2;+0:6]-[NH2;D1;+0:7].[S;H0;D1;+0:8]=[C;H0;D2;+0:9]=[N;H0;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[NH2;D1;+0:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:9](-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]):[s;H0;D2;+0:8]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | This compound was prepared from cyanamide, 1-(4-isothiocyanatophenyl)-4-methylpiperazine (of Example 1) and 3-cyanophenacyl bromide (Maybridge Chemical Co. Ltd.) following the procedure used in Example 24. Mass spectrum (ES) MH+=419.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Cyanamide.Ketone.Isothiocyanate | Ketone.Primary amine.Secondary amine | null | c1cscn1 | C1C[NH]CC[NH]1.c1ccccc1.c1cscn1.c1ccccc1 | HBr | null | null | null | CN1CCN(c2ccc(N=C=S)cc2)CC1.N#CN.N#Cc1cccc(C(=O)CBr)c1>>CN1CCN(c2ccc(Nc3nc(N)c(C(=O)c4cccc(C#N)c4)s3)cc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5f7428243e1e42a2ae90f190d4aceb30 | CC(=O)NC[C@H]1CN(c2cc(F)c(I)c(F)c2)C(=O)O1.COc1ccc(-c2ccc(N3C[C@H](CNC(C)=O)OC3=O)cc2F)cn1>>COc1ccc(-c2c(F)cc(N3C[C@H](CNC(C)=O)OC3=O)cc2F)cn1 | FC=1C=C(C=C(C1I)F)N1C(O[C@H](C1)CNC(C)=O)=O.FC=1C=C(C=CC1C=1C=NC(=CC1)OC)N1C(O[C@H](C1)CNC(C)=O)=O>>FC=1C=C(C=C(C1C=1C=NC(=CC1)OC)F)N1C(O[C@H](C1)CNC(C)=O)=O | CC(=O)NC[C@H]1CN(c2cc(F)c(I)c([F:9])c2)C(=O)O1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:10][c:11]([N:12]3[CH2:13][C@H:14]([CH2:15][NH:16][C:17]([CH3:18])=[O:19])[O:20][C:21]3=[O:22])[cH:23][c:24]2[F:25])[cH:26][n:27]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[c:8]([F:9])[cH:10][c:11]([N:12]3[CH2:13][C@H:... | CC(=O)NC[C@H]1CN(c2cc(F)c(I)c(F)c2)C(=O)O1.COc1ccc(-c2ccc(N3C[C@H](CNC(C)=O)OC3=O)cc2F)cn1 | COc1ccc(-c2c(F)cc(N3C[C@H](CNC(C)=O)OC3=O)cc2F)cn1 | null | null | null | Functional Group Interconversion | OtherReaction | d4b5322c27601307394c725f5c94ebd4103ee51f47d69dfacf778281cc0e2eb6 | 721c7aa90abd60eb14ef592153438764d721e980179827d6757b21b618ed0ef2 | O=C1OCCN1c1ccc(-c2cccnc2)cc1 | C-C(=O)-N-C-[C@@H]1-C-N(-c2:c:c(-F):c(-I):c(-[F;H0;D1;+0:1]):c:2)-C(=O)-O-1.[#7;a:2]:[c:3]:[c:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]>>[#7;a:2]:[c:3]:[c:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[F;H0;D1;+0:1]):[c:8]:[c:9] | null | [] | null | null | null | null | N-({(5S)-3-[3,5-difluoro-4-(6-methoxypyridin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide is prepared by the route described in Example 1 substituting N-{[(5S)-3-(3,5-difluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide for N-({(5S)-3-[3-fluoro-4-(6-methoxypyridin-3-yl)phenyl]-2-oxo-1,3-oxazolid... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Carbamic ester.Ether.Secondary amide | Aromatic halide | C1COCN1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccncc1.c1ccccc1.C1COC[NH]1 | HF.I- | null | null | null | CC(=O)NC[C@H]1CN(c2cc(F)c(I)c(F)c2)C(=O)O1.COc1ccc(-c2ccc(N3C[C@H](CNC(C)=O)OC3=O)cc2F)cn1>>COc1ccc(-c2c(F)cc(N3C[C@H](CNC(C)=O)OC3=O)cc2F)cn1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-481e7c54b6434612a675d5ca6d8123d4 | CC(=O)NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1.CC(C)(C)OC(=O)NC[C@H]1CN(c2ccc(I)cc2)C(=O)O1>>CC(=O)NC[C@H]1CN(c2ccc(C3CCC(=O)NC3)cc2)C(=O)O1 | IC1=CC=C(C=C1)N1C(O[C@H](C1)CNC(OC(C)(C)C)=O)=O.FC=1C=C(C=CC1I)N1C(O[C@H](C1)CNC(C)=O)=O>>O=C1O[C@H](CN1C1=CC=C(C=C1)C1CNC(CC1)=O)CNC(C)=O | F[c:20]1[c:12](I)[cH:11][cH:10][c:9]([N:8]2[CH2:7][C@H:6]([CH2:5][NH:4][C:2]([CH3:1])=[O:3])[O:24][C:22]2=[O:23])[cH:21]1.CC(C)(C)OC(=O)N[CH2:14][C@@H:13]1O[C:16](=[O:17])[N:18](c2ccc(I)[cH:15]c2)[CH2:19]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([CH:13]3[CH2:14][CH2:15][C:16](=... | CC(=O)NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1.CC(C)(C)OC(=O)NC[C@H]1CN(c2ccc(I)cc2)C(=O)O1 | CC(=O)NC[C@H]1CN(c2ccc(C3CCC(=O)NC3)cc2)C(=O)O1 | null | null | null | C-C Coupling | OtherReaction | 59e32096c760eae73ed2de06f4095cf7d765ae537c9f5008658d9e89b5c8e125 | e1bea111e0647ea8b1abfb30b0498d8c9c2e13198d7d09566034da932ea95a38 | O=C1CCC(c2ccc(N3CCOC3=O)cc2)CN1 | C-C(-C)(-C)-O-C(=O)-N-[CH2;D2;+0:1]-[C@@H;D3;+0:2]1-O-[C;H0;D3;+0:3](=[O;D1;H0:4])-[N;H0;D3;+0:5](-c2:c:[cH;D2;+0:6]:c(-I):c:c:2)-[C:7]-1.F-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[c:12]:[c;H0;D3;+0:13]:1-I>>[O;D1;H0:4]=[C;H0;D3;+0:3]1-[CH2;D2;+0:6]-[CH2;D2;+0:1]-[CH;D3;+0:2](-[c;H0;D3;+0:13]2:[c:12]:[c:11]:[c:10]:[c:9]:[c... | null | [] | null | null | null | null | N-({(5S)-2-oxo-3-[4-(6-oxopiperidin-3-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamide is prepared by the route described in Example 1 substituting tert-butyl [(5S)-3-(4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methylcarbamate for N-{[(5S)-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide. 1H-NMR (DMSO) δ:... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Carbamic ester.Carbamic ester.Ether.Ether.Boc | Secondary amide | c1ccccc1.C1COC[NH]1.c1ccccc1 | c1ccccc1.C1CCNCC1 | C1COC[NH]1.c1ccccc1.C1CCNCC1 | HF.I- | null | null | null | CC(=O)NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1.CC(C)(C)OC(=O)NC[C@H]1CN(c2ccc(I)cc2)C(=O)O1>>CC(=O)NC[C@H]1CN(c2ccc(C3CCC(=O)NC3)cc2)C(=O)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b8b7a9a119eb41aeb93ede6115a10d01 | CI.COc1ccc(-c2ccc(N3C[C@H](CNC(C)=O)OC3=O)cc2)cn1>>CC(=O)NC[C@H]1CN(c2ccc(-c3ccc(=O)n(C)c3)cc2)C(=O)O1 | C1CCOC1.COC1=CC=C(C=N1)C1=CC=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O.C([O-])([O-])=O.[K+].[K+].CI>>CN1C=C(C=CC1=O)C1=CC=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O | I[CH3:19].C[O:17][c:16]1[cH:15][cH:14][c:13](-[c:12]2[cH:11][cH:10][c:9]([N:8]3[CH2:7][C@H:6]([CH2:5][NH:4][C:2]([CH3:1])=[O:3])[O:25][C:23]3=[O:24])[cH:22][cH:21]2)[cH:20][n:18]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16](=[O:17])[n:18]([CH3:19])[cH:2... | CI.COc1ccc(-c2ccc(N3C[C@H](CNC(C)=O)OC3=O)cc2)cn1 | CC(=O)NC[C@H]1CN(c2ccc(-c3ccc(=O)n(C)c3)cc2)C(=O)O1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 545dd64706b916c5c1e0993ccc3faf9b2ae2a984dff2896afa16f308b6704fa2 | 44ce3ef111697e4edd80a3a62efdfdfb9c6acd9c324ef9a7c10ca658a5992f13 | O=C1OCCN1c1ccc(-c2ccc(=O)[nH]c2)cc1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[n;H0;D2;+0:7]:1.I-[CH3;D1;+0:8]>>[CH3;D1;+0:8]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[c:3]:[c;H0;D3;+0:2]:1=[O;H0;D1;+0:1] | 53 | [{"value": 53.0, "product": "CN1C=C(C=CC1=O)C1=CC=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | To a stirred anhydrous THF (10 mL) mixture of N-({(5S)-3-[4-(6-methoxypyridin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (0.10 g, 0.29 mmol) in a sealed tube, is added potassium carbonate (0.04 g, 0.58 mmol) and methyl iodide (0.1 mL, 1.7 mmol). The mixture is heated to 85° C. for 16 hours. The reaction is... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccncc1 | c1ccncc1 | C1COC[NH]1.c1ccccc1.c1ccncc1 | HI | C(Cl)Cl | 85 | null | CI.COc1ccc(-c2ccc(N3C[C@H](CNC(C)=O)OC3=O)cc2)cn1>C(Cl)Cl>CC(=O)NC[C@H]1CN(c2ccc(-c3ccc(=O)n(C)c3)cc2)C(=O)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5c6bb1e0d3264955b588e9c074389bb6 | CC(=O)NC[C@H]1CN(c2ccc(-c3ccc(=O)n(C)c3)cc2)C(=O)O1>>CC(=O)NC[C@H]1CN(c2ccc(C3CCC(=O)N(C)C3)cc2)C(=O)O1 | CN1C=C(C=CC1=O)C1=CC=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O>>CN1CC(CCC1=O)C1=CC=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16](=[O:17])[n:18]([CH3:19])[cH:20]3)[cH:21][cH:22]2)[C:23](=[O:24])[O:25]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([CH:13]3[CH2:14][CH2:15][C:16](=[O:17])[N:18]([CH3:19])[... | CC(=O)NC[C@H]1CN(c2ccc(-c3ccc(=O)n(C)c3)cc2)C(=O)O1 | CC(=O)NC[C@H]1CN(c2ccc(C3CCC(=O)N(C)C3)cc2)C(=O)O1 | null | [Pd] | CO | Reduction | OtherReaction | c3195e041c676c98fe57174265b77b3d65854f9e1e38d3c19cbfffe2c63e429c | a9abb915c2e8fb5c88d9357a865a3b933b515d3da17c0f40274f1e391bda35ae | O=C1CCC(c2ccc(N3CCOC3=O)cc2)CN1 | [C;D1;H3:1]-[n;H0;D3;+0:2]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9]):[cH;D2;+0:10]:[cH;D2;+0:11]:[c;H0;D3;+0:12]:1=[O;D1;H0:13]>>[C;D1;H3:1]-[N;H0;D3;+0:2]1-[CH2;D2;+0:3]-[CH;D3;+0:4](-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9])-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[C;H0;D3;+0:12]-1=[O;D1;H0:13] | 97.4 | [{"value": 96.0, "product": "CN1CC(CCC1=O)C1=CC=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.4, "product": "CN1CC(CCC1=O)C1=CC=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a mixture of N-({(5S)-3-[4-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (0.179 g. 0.52 mmol) in 20 mL of MeOH is added 0.05 g of 10% palladium on activated charcoal. The mixture is hydrogenated at 50 psi for 16 hours. The reaction mixture is filtered through celite, sili... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amide | c1ccncc1 | C1CC[NH]CC1 | C1COC[NH]1.c1ccccc1.C1CC[NH]CC1 | null | [Pd].CO | null | 16 | CC(=O)NC[C@H]1CN(c2ccc(-c3ccc(=O)n(C)c3)cc2)C(=O)O1>[Pd].CO>CC(=O)NC[C@H]1CN(c2ccc(C3CCC(=O)N(C)C3)cc2)C(=O)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f5a70fb75d8f4ab78c65ac2e0f2a45cd | CC(=O)NC[C@H]1CN(c2cc(F)c(I)c(F)c2)C(=O)O1.CC(=O)NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1>>CC(=O)NC[C@H]1CN(c2cc(F)c(C3CCNC(=O)C3)c(F)c2)C(=O)O1 | FC=1C=C(C=C(C1I)F)N1C(O[C@H](C1)CNC(C)=O)=O.FC=1C=C(C=CC1I)N1C(O[C@H](C1)CNC(C)=O)=O>>FC=1C=C(C=C(C1C1CC(NCC1)=O)F)N1C(O[C@H](C1)CNC(C)=O)=O | I[c:13]1[c:11]([F:12])[cH:10][c:9]([N:8]2[CH2:7][C@H:6]([CH2:5][NH:4][C:2]([CH3:1])=[O:3])[O:26][C:24]2=[O:25])[cH:23][c:21]1[F:22].O=C1O[C@@H]([CH2:16][NH:17][C:18](=[O:19])[CH3:20])CN1c1cc(F)[c:14](I)[cH:15]c1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][c:11]([F:12])[c:13]([CH:14]3[CH2:15][CH... | CC(=O)NC[C@H]1CN(c2cc(F)c(I)c(F)c2)C(=O)O1.CC(=O)NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1 | CC(=O)NC[C@H]1CN(c2cc(F)c(C3CCNC(=O)C3)c(F)c2)C(=O)O1 | null | null | null | C-C Coupling | OtherReaction | 9848f145d33a3b77976f5af411dab89172424ee5e8c4f6ad59dcb6388908519f | 8f99d3d6d09d378cd3451a4aabedce8298e57da208307a564bd3a9b8c5a1a312 | O=C1CC(c2ccc(N3CCOC3=O)cc2)CCN1 | F-c1:c:c(-N2-C-[C@@H](-[CH2;D2;+0:1]-[#7:2]-[C:3](-[CH3;D1;+0:4])=[O;D1;H0:5])-O-C-2=O):c:[cH;D2;+0:6]:[c;H0;D3;+0:7]:1-I.I-[c;H0;D3;+0:8](:[c:9](-[F;D1;H0:10]):[c:11]):[c:12](-[F;D1;H0:13]):[c:14]>>[F;D1;H0:10]-[c:9](:[c:11]):[c;H0;D3;+0:8](-[CH;D3;+0:7]1-[CH2;D2;+0:6]-[CH2;D2;+0:1]-[#7:2]-[C:3](=[O;D1;H0:5])-[CH2;D2;... | null | [] | null | null | null | null | N-({(5S)-3-[3,5-difluoro-4-(2-oxopiperidin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide is prepared as in the route described in Example 16 substituting N-{[(5S)-3-(3,5-difluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide for 1 N-{[(5S)-3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Carbamic ester.Ether | null | c1ccccc1.C1COCN1.c1ccccc1 | c1ccccc1.C1CCNCC1 | C1COC[NH]1.c1ccccc1.C1CCNCC1 | HF.I- | null | null | null | CC(=O)NC[C@H]1CN(c2cc(F)c(I)c(F)c2)C(=O)O1.CC(=O)NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1>>CC(=O)NC[C@H]1CN(c2cc(F)c(C3CCNC(=O)C3)c(F)c2)C(=O)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-603ab36590b94febb01366d65d2beff1 | CC(=O)NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1.CC(C)(C)OC(=O)NC[C@H]1CN(c2ccc(I)cc2)C(=O)O1>>CC(=O)NC[C@H]1CN(c2ccc(C3CCNC(=O)C3)cc2)C(=O)O1 | IC1=CC=C(C=C1)N1C(O[C@H](C1)CNC(OC(C)(C)C)=O)=O.FC=1C=C(C=CC1I)N1C(O[C@H](C1)CNC(C)=O)=O>>O=C1O[C@H](CN1C1=CC=C(C=C1)C1CC(NCC1)=O)CNC(C)=O | F[c:20]1[c:12](I)[cH:11][cH:10][c:9]([N:8]2[CH2:7][C@H:6]([CH2:5][NH:4][C:2]([CH3:1])=[O:3])[O:24][C:22]2=[O:23])[cH:21]1.CC(C)(C)O[C:17]([NH:16][CH2:15][C@H:14]1CN(c2cc[c:13](I)[cH:19]c2)C(=O)O1)=[O:18]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([CH:13]3[CH2:14][CH2:15][NH:16][C:... | CC(=O)NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1.CC(C)(C)OC(=O)NC[C@H]1CN(c2ccc(I)cc2)C(=O)O1 | CC(=O)NC[C@H]1CN(c2ccc(C3CCNC(=O)C3)cc2)C(=O)O1 | null | null | null | C-C Coupling | OtherReaction | 5d72289eadb17142a403fba2d58f954256fd4195024b0107234b1eac52ee5906 | e1bea111e0647ea8b1abfb30b0498d8c9c2e13198d7d09566034da932ea95a38 | O=C1CC(c2ccc(N3CCOC3=O)cc2)CCN1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]-[C:4]-[C@H;D3;+0:5]1-C-N(-c2:c:[cH;D2;+0:6]:[c;H0;D3;+0:7](-I):c:c:2)-C(=O)-O-1.F-[c;H0;D3;+0:8]1:[c:9]:[c:10]:[c:11]:[c:12]:[c;H0;D3;+0:13]:1-I>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[#7:3]-[C:4]-[CH2;D2;+0:5]-[CH;D3;+0:7](-[c;H0;D3;+0:13]2:[c:12]:[c:11]:[c:10]:[c:9]:[cH;D2;+0:8... | null | [] | null | null | null | null | N-({(5S)-2-oxo-3-[4-(2-oxopiperidin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)acetamide is prepared as described in the route described in Example 16 substituting tert-butyl [(5S)-3-(4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methylcarbamate for N-{[(5S)-3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide. ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Carbamic ester.Carbamic ester.Ether.Ether.Boc | Secondary amide | c1ccccc1.C1COCN1.c1ccccc1 | c1ccccc1.C1CCNCC1 | C1COC[NH]1.c1ccccc1.C1CCNCC1 | HF.I- | null | null | null | CC(=O)NC[C@H]1CN(c2ccc(I)c(F)c2)C(=O)O1.CC(C)(C)OC(=O)NC[C@H]1CN(c2ccc(I)cc2)C(=O)O1>>CC(=O)NC[C@H]1CN(c2ccc(C3CCNC(=O)C3)cc2)C(=O)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-68f084637a2845fca977375ed451ee03 | CI.COc1cc(-c2ccc(N3C[C@H](CNC(C)=O)OC3=O)cc2)ccn1>>CC(=O)NC[C@H]1CN(c2ccc(-c3ccn(C)c(=O)c3)cc2)C(=O)O1 | C1CCOC1.COC1=NC=CC(=C1)C1=CC=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O.C([O-])([O-])=O.[K+].[K+].CI>>CN1C(C=C(C=C1)C1=CC=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O)=O | I[CH3:17].C[O:19][c:18]1[n:16][cH:15][cH:14][c:13](-[c:12]2[cH:11][cH:10][c:9]([N:8]3[CH2:7][C@H:6]([CH2:5][NH:4][C:2]([CH3:1])=[O:3])[O:25][C:23]3=[O:24])[cH:22][cH:21]2)[cH:20]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][n:16]([CH3:17])[c:18](=[O:19])[cH:2... | CI.COc1cc(-c2ccc(N3C[C@H](CNC(C)=O)OC3=O)cc2)ccn1 | CC(=O)NC[C@H]1CN(c2ccc(-c3ccn(C)c(=O)c3)cc2)C(=O)O1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 545dd64706b916c5c1e0993ccc3faf9b2ae2a984dff2896afa16f308b6704fa2 | 44ce3ef111697e4edd80a3a62efdfdfb9c6acd9c324ef9a7c10ca658a5992f13 | O=C1OCCN1c1ccc(-c2cc[nH]c(=O)c2)cc1 | C-[O;H0;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[n;H0;D2;+0:7]:1.I-[CH3;D1;+0:8]>>[CH3;D1;+0:8]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[c:4]:[c:3]:[c;H0;D3;+0:2]:1=[O;H0;D1;+0:1] | 69 | [{"value": 69.0, "product": "CN1C(C=C(C=C1)C1=CC=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | To a stirred anhydrous THF (10 mL) mixture of N-({(5S)-3-[4-(2-methoxypyridin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (0.667 g, 1.95 mmol) in a sealed tube, is added potassium carbonate (0.807 g, 6.0 mmol) and methyl iodide (1 mL, 17 mmol). The mixture is heated to 85° C. for 16 hours. The reaction is c... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccncc1 | c1ccncc1 | C1COC[NH]1.c1ccccc1.c1ccncc1 | HI | C(Cl)Cl | 85 | null | CI.COc1cc(-c2ccc(N3C[C@H](CNC(C)=O)OC3=O)cc2)ccn1>C(Cl)Cl>CC(=O)NC[C@H]1CN(c2ccc(-c3ccn(C)c(=O)c3)cc2)C(=O)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aafc07e1d0ec45f3bf9d814970cd12ea | CC(=O)NC[C@H]1CN(c2ccc(-c3ccn(C)c(=O)c3)cc2)C(=O)O1>>CC(=O)NC[C@H]1CN(c2ccc(C3CCN(C)C(=O)C3)cc2)C(=O)O1 | CN1C(C=C(C=C1)C1=CC=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O)=O>>CN1C(CC(CC1)C1=CC=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O)=O | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][n:16]([CH3:17])[c:18](=[O:19])[cH:20]3)[cH:21][cH:22]2)[C:23](=[O:24])[O:25]1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([CH:13]3[CH2:14][CH2:15][N:16]([CH3:17])[C:18](=[O:19])[... | CC(=O)NC[C@H]1CN(c2ccc(-c3ccn(C)c(=O)c3)cc2)C(=O)O1 | CC(=O)NC[C@H]1CN(c2ccc(C3CCN(C)C(=O)C3)cc2)C(=O)O1 | null | [Pd] | CO | Reduction | OtherReaction | c3195e041c676c98fe57174265b77b3d65854f9e1e38d3c19cbfffe2c63e429c | a9abb915c2e8fb5c88d9357a865a3b933b515d3da17c0f40274f1e391bda35ae | O=C1CC(c2ccc(N3CCOC3=O)cc2)CCN1 | [C;D1;H3:1]-[n;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[cH;D2;+0:11]:[c;H0;D3;+0:12]:1=[O;D1;H0:13]>>[C;D1;H3:1]-[N;H0;D3;+0:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[CH;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10])-[CH2;D2;+0:11]-[C;H0;D3;+0:12]-1=[O;D1;H0:13] | 97.5 | [{"value": 96.0, "product": "CN1C(CC(CC1)C1=CC=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.5, "product": "CN1C(CC(CC1)C1=CC=C(C=C1)N1C(O[C@H](C1)CNC(C)=O)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a mixture of N-({(5S)-3-[4-(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (0.170 g. 0.49 mmol) in 20 mL of MeOH is added 0.05 g of 10% palladium on activated charcoal. The mixture is hydrogenated at 50 psi for 16 hours. The reaction mixture is filtered through celite, sili... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amide | c1ccncc1 | C1CC[NH]CC1 | C1COC[NH]1.c1ccccc1.C1CC[NH]CC1 | null | [Pd].CO | null | 16 | CC(=O)NC[C@H]1CN(c2ccc(-c3ccn(C)c(=O)c3)cc2)C(=O)O1>[Pd].CO>CC(=O)NC[C@H]1CN(c2ccc(C3CCN(C)C(=O)C3)cc2)C(=O)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-38f98b5e5d954dd4aefeef4cc01d73b6 | Cc1ccc(S(=O)(=O)N/N=C/C(Cl)Cl)cc1.NC[C@H]1CN(c2cc(F)c(C3CCC(=O)NC3)c(F)c2)C(=O)O1>>O=C1CCC(c2c(F)cc(N3C[C@H](Cn4ccnn4)OC3=O)cc2F)CN1 | NC[C@H]1CN(C(O1)=O)C1=CC(=C(C(=C1)F)C1CCC(NC1)=O)F.FC=1C=C(C=C(C1I)F)N1C(O[C@H](C1)CNC(C)=O)=O.CCN(CC)CC.ClC(\C=N\NS(=O)(=O)C1=CC=C(C=C1)C)Cl>>FC1=C(C(=CC(=C1)N1C(O[C@H](C1)CN1N=NC=C1)=O)F)C1CCC(NC1)=O | Cc1ccc(S(=O)(=O)[NH:19]/[N:18]=[CH:17]/[CH:16](Cl)Cl)cc1.[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([c:6]2[c:7]([F:8])[cH:9][c:10]([N:11]3[CH2:12][C@H:13]([CH2:14][NH2:15])[O:20][C:21]3=[O:22])[cH:23][c:24]2[F:25])[CH2:26][NH:27]1>>[O:1]=[C:2]1[CH2:3][CH2:4][CH:5]([c:6]2[c:7]([F:8])[cH:9][c:10]([N:11]3[CH2:12][C@H:13]([CH2:14][n... | Cc1ccc(S(=O)(=O)N/N=C/C(Cl)Cl)cc1.NC[C@H]1CN(c2cc(F)c(C3CCC(=O)NC3)c(F)c2)C(=O)O1 | O=C1CCC(c2c(F)cc(N3C[C@H](Cn4ccnn4)OC3=O)cc2F)CN1 | null | null | CO | Functional Group Interconversion | OtherReaction | 5075942d1c359ffbea0abc7bda1d363acb35365d84e84d19f453041d6c512a7e | 642892d0a5f6fd725597bcb867e2f43b9086bb600d415ccf63e67d9536d6e549 | O=C1CCC(c2ccc(N3C[C@H](Cn4ccnn4)OC3=O)cc2)CN1 | C-c1:c:c:c(-S(=O)(=O)-[NH;D2;+0:1]/[N;H0;D2;+0:2]=[CH;D2;+0:3]/[CH;D3;+0:4](-Cl)-Cl):c:c:1.[#8:5]-[C:6]-[C:7]-[NH2;D1;+0:8]>>[#8:5]-[C:6]-[C:7]-[n;H0;D3;+0:8]1:[cH;D2;+0:4]:[cH;D2;+0:3]:[n;H0;D2;+0:2]:[n;H0;D2;+0:1]:1 | null | [] | null | null | 16 | HOUR | 5-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2,6-difluorophenyl}piperidin-2-one (0.1 g, 0.31 mmol) (prepared by the route described in Example 1, substituting N-{[(5S)-3-(3,5-difluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide) is dissolved in MeOH (2 mL). To this mixture is added Et3N (0.125 ml,... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Hydrazone.Tosylate.Secondary halide.Secondary halide.Primary amine | null | c1ccccc1 | c1c[nH]nn1 | C1CCNCC1.c1ccccc1.C1COC[NH]1.c1c[nH]nn1 | TsOH.HCl | CO | null | 16 | Cc1ccc(S(=O)(=O)N/N=C/C(Cl)Cl)cc1.NC[C@H]1CN(c2cc(F)c(C3CCC(=O)NC3)c(F)c2)C(=O)O1>CO>O=C1CCC(c2c(F)cc(N3C[C@H](Cn4ccnn4)OC3=O)cc2F)CN1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8ef35b9c9c5c40bcabb7b408e1cb86f0 | C1CCNC1.COC(=O)CC(C)=O>>COC(=O)C=C(C)C1CCCN1 | C(CC(=O)C)(=O)OC.N1CCCC1>>N1C(CCC1)C(=CC(=O)OC)C | [CH2:8]1[CH2:9][CH2:10][CH2:11][NH:12]1.O=[C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH3:7]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[C:6]([CH3:7])[CH:8]1[CH2:9][CH2:10][CH2:11][NH:12]1 | C1CCNC1.COC(=O)CC(C)=O | COC(=O)C=C(C)C1CCCN1 | null | O.C1(=CC=C(C=C1)S(=O)(=O)O)C | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 8660069fb91e5b1c8f8d2e6b91aa0e7d72f23b0e3df16a0b8c6114590ddc28ad | 79a946b42eb7e7aee42e09efe41630192c1745e07085cd7f7f88cc7b599f9082 | C1CCNC1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7].[#7:8]1-[C:9]-[C:10]-[C:11]-[CH2;D2;+0:12]-1>>[C;D1;H3:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[CH;D2;+0:3]=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:12]1-[#7:8]-[C:9]-[C:10]-[C:11]-1 | 99.5 | [{"value": 99.0, "product": "N1C(CCC1)C(=CC(=O)OC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.5, "product": "N1C(CCC1)C(=CC(=O)OC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | Methyl acetoacetate (20 g, 172.23 mmol) was dissolved in 250 mL of toluene, and then pyrrolidine (43 ml, 516.70 mmol) and p-toluenesulfonic acid hydrate (about 100 mg) were added dropwise. After installing a Dean-Stark separator to the reactor, the reaction mixture was refluxed 140° C. for two days, and then solvent wa... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ester | C1CCNC1 | C1CCNC1 | C1CCNC1 | HO- | O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C1(=CC=CC=C1)C | 140 | null | C1CCNC1.COC(=O)CC(C)=O>O.C1(=CC=C(C=C1)S(=O)(=O)O)C.C1(=CC=CC=C1)C>COC(=O)C=C(C)C1CCCN1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c4f6c0a039404fa9b84557e51bc4c6bf | C1CCNC1.CCOC(=O)CC(C)=O>>CCOC(=O)C=C(C)C1CCCN1 | C(CC(=O)C)(=O)OCC.N1CCCC1>>N1C(CCC1)C(=CC(=O)OCC)C | [CH2:9]1[CH2:10][CH2:11][CH2:12][NH:13]1.O=[C:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]=[C:7]([CH3:8])[CH:9]1[CH2:10][CH2:11][CH2:12][NH:13]1 | C1CCNC1.CCOC(=O)CC(C)=O | CCOC(=O)C=C(C)C1CCCN1 | null | null | null | C-C Coupling | OtherReaction | 8660069fb91e5b1c8f8d2e6b91aa0e7d72f23b0e3df16a0b8c6114590ddc28ad | 79a946b42eb7e7aee42e09efe41630192c1745e07085cd7f7f88cc7b599f9082 | C1CCNC1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].[#7:8]1-[C:9]-[C:10]-[C:11]-[CH2;D2;+0:12]-1>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[CH;D2;+0:3]=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:12]1-[#7:8]-[C:9]-[C:10]-[C:11]-1 | null | [] | null | null | null | null | Ethyl 3-tetrahydropyrrolyl-2-butenoate was prepared (21 g, 99%) from ethyl acetoacetate (15.0 g, 115.26 mmol) and pyrrolidine (71.1 mL, 345.78 mmol) in the same manner as described in the above Example 1 (1), and the obtained product was identified with the following NMR data.
Conditions: See reaction.notes.procedure_d... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ester | C1CCNC1 | C1CCNC1 | C1CCNC1 | HO- | null | null | null | C1CCNC1.CCOC(=O)CC(C)=O>>CCOC(=O)C=C(C)C1CCCN1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b23c8ba54c484e1bafaf208e0e2e4633 | C1CCNC1.C=CCOC(=O)CC(C)=O>>C=CCOC(=O)C=C(C)C1CCCN1 | C(CC(=O)C)(=O)OCC=C.N1CCCC1>>N1C(CCC1)C(=CC(=O)OCC=C)C | [CH2:10]1[CH2:11][CH2:12][CH2:13][NH:14]1.O=[C:8]([CH2:7][C:5]([O:4][CH2:3][CH:2]=[CH2:1])=[O:6])[CH3:9]>>[CH2:1]=[CH:2][CH2:3][O:4][C:5](=[O:6])[CH:7]=[C:8]([CH3:9])[CH:10]1[CH2:11][CH2:12][CH2:13][NH:14]1 | C1CCNC1.C=CCOC(=O)CC(C)=O | C=CCOC(=O)C=C(C)C1CCCN1 | null | null | null | C-C Coupling | OtherReaction | 8660069fb91e5b1c8f8d2e6b91aa0e7d72f23b0e3df16a0b8c6114590ddc28ad | 79a946b42eb7e7aee42e09efe41630192c1745e07085cd7f7f88cc7b599f9082 | C1CCNC1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7]-[C:8]=[C;D1;H2:9].[#7:10]1-[C:11]-[C:12]-[C:13]-[CH2;D2;+0:14]-1>>[C;D1;H2:9]=[C:8]-[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[CH;D2;+0:3]=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH;D3;+0:14]1-[#7:10]-[C:11]-[C:12]-[C:13]-1 | null | [] | null | null | null | null | Allyl 3-tetrahydropyrrolyl-2-butenoate was prepared (4.7 g, 68%) in the same manner as described in the above Example 1 (1) from allyl acetoacetate (5.0 g, 35.17 mmol) and pyrrolidine (8.8 mL, 105.51 mmol), and the obtained product was identified with the following 1H NMR data.
Conditions: See reaction.notes.procedure_... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ester | C1CCNC1 | C1CCNC1 | C1CCNC1 | HO- | null | null | null | C1CCNC1.C=CCOC(=O)CC(C)=O>>C=CCOC(=O)C=C(C)C1CCCN1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-96ae0b4ef29e47f48fb533915a460abe | COC(=O)C=C(C)C1CCCN1.O.O=C1c2ccccc2C(=O)N1CBr>>COC(=O)C(CN1C(=O)c2ccccc2C1=O)C(C)=O | N1C(CCC1)C(=CC(=O)OC)C.BrCN1C(C=2C(C1=O)=CC=CC2)=O.Cl.O>>C1(C=2C(C(N1CC(C(=O)OC)C(C)=O)=O)=CC=CC2)=O | C1CNC([C:18](=[CH:5][C:3]([O:2][CH3:1])=[O:4])[CH3:19])C1.[OH2:20].Br[CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16]1=[O:17]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[C:16]1=[O:17])[C:18]([CH3:19])=[O:20] | COC(=O)C=C(C)C1CCCN1.O.O=C1c2ccccc2C(=O)N1CBr | COC(=O)C(CN1C(=O)c2ccccc2C1=O)C(C)=O | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 0dc29a751f8e39c42176c69c70cd6d74b167d123f582ba8e6e42b4cfcf20a324 | e7542302dea48a79cdeb319bd616ca61700e1eb51eca81328aa5c73cb500b762 | O=C1NC(=O)c2ccccc21 | Br-[CH2;D2;+0:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]-[C:7]-1=[O;D1;H0:8].[C;D1;H3:9]-[C;H0;D3;+0:10](=[CH;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15])-C1-C-C-C-N-1.[OH2;D0;+0:16]>>[C;D1;H3:9]-[C;H0;D3;+0:10](=[O;H0;D1;+0:16])-[CH;D3;+0:11](-[CH2;D2;+0:1]-[#7:2]1-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]-[C:7]-1=[O;D... | 68 | [{"value": 68.0, "product": "C1(C=2C(C(N1CC(C(=O)OC)C(C)=O)=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Methyl 3-tetrahydropyrrolyl-2-butenoate (29.0 g, 171.3 mmol) and N-(bromomethyl)phthalimide (43 g, 179.91 mmol) were dissolved in 250 ml of dimethylformamide, and the resulting mixture was then stirred at room temperature for 16 hours under a nitrogen atmosphere. After checking completion of the reaction with TLC, 1N H... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Substituted dicarboximide.Secondary amine | Ketone.Ester.Substituted dicarboximide | C1CCNC1 | null | c1ccc2c(c1)C[NH]C2 | HBr | CN(C=O)C | null | 16 | COC(=O)C=C(C)C1CCCN1.O.O=C1c2ccccc2C(=O)N1CBr>CN(C=O)C>COC(=O)C(CN1C(=O)c2ccccc2C1=O)C(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-beaa02d0a3f34642896af054ec129f95 | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(F)cccc21>>COC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1 | NCC(C(=O)OC)C1(OCCO1)C.FC1=C2C(C(=O)OC2=O)=CC=C1>>FC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OC)C1(OCCO1)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][NH2:7])[C:19]1([CH3:20])[O:21][CH2:22][CH2:23][O:24]1.O1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([F:15])[c:16]2[C:17]1=[O:18]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([F:15])[c:16]2[C:17]1=[O:18])[C:19]1([CH3:20])[O:21][... | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(F)cccc21 | COC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[c:13](:[c:14]):[c:11](:[c:12])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | Methyl 3-(4-fluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.24 g, 28%) in the same manner as described in the above example 5 (1) from methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.50 g, 2.64 mmol) and 3-fluorophthalic anhydride (0.57 g, 3.43 mmol), an... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(F)cccc21>>COC(=O)C(CN1C(=O)c2cccc(F)c2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-55e268810b43421a99d2245b5297b31f | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(F)ccc(F)c21>>COC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C1(C)OCCO1 | O=C1N(C(C=2CCCCC12)=O)CC(C(=O)OC)C1(OCCO1)C.NCC(C(=O)OC)C1(OCCO1)C.FC1=C2C(C(=O)OC2=O)=C(C=C1)F>>FC1=C2C(N(C(C2=C(C=C1)F)=O)CC(C(=O)OC)C1(OCCO1)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][NH2:7])[C:20]1([CH3:21])[O:22][CH2:23][CH2:24][O:25]1.O1[C:8](=[O:9])[c:10]2[c:11]([F:12])[cH:13][cH:14][c:15]([F:16])[c:17]2[C:18]1=[O:19]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[c:11]([F:12])[cH:13][cH:14][c:15]([F:16])[c:17]2[C:18]1=[O:19])[C:20]1([C... | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(F)ccc(F)c21 | COC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[c:13](:[c:14]):[c:11](:[c:12])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | Methyl 3-(4,7-difluoro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.27 g, 31%) in the same manner as described in the above example 5. (1) from methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.47 g, 2.47 mmol) and 3,6-difluorophthalic anhydride (0.50 g, 2.72 ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c(F)ccc(F)c21>>COC(=O)C(CN1C(=O)c2c(F)ccc(F)c2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-12877900e40941db975f259d46996cee | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c1cccc2[N+](=O)[O-]>>COC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C1(C)OCCO1 | NCC(C(=O)OC)C1(OCCO1)C.[N+](=O)([O-])C1=C2C(C(=O)OC2=O)=CC=C1>>[N+](=O)([O-])C1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OC)C1(OCCO1)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][NH2:7])[C:21]1([CH3:22])[O:23][CH2:24][CH2:25][O:26]1.O1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[c:18]2[C:19]1=[O:20]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[c:18]2[C:19... | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c1cccc2[N+](=O)[O-] | COC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[c:13](:[c:14]):[c:11](:[c:12])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | Methyl 3-(4-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.27 g, 28%) in the same manner as described in the above example 5 (1) from methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.50 g, 2.64 mmol) and 3-nitrophthalic anhydride (0.57 g, 3.43 mmol), and ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2c1cccc2[N+](=O)[O-]>>COC(=O)C(CN1C(=O)c2cccc([N+](=O)[O-])c2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7191e37235674d979dcb6209ad9e8a6c | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc([N+](=O)[O-])ccc21>>COC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C1(C)OCCO1 | NCC(C(=O)OC)C1(OCCO1)C.[N+](=O)([O-])C=1C=C2C(C(=O)OC2=O)=CC1>>[N+](=O)([O-])C=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C1(OCCO1)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][NH2:7])[C:21]1([CH3:22])[O:23][CH2:24][CH2:25][O:26]1.O1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][c:18]2[C:19]1=[O:20]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][c:18]2[C:19... | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc([N+](=O)[O-])ccc21 | COC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[c:13](:[c:14]):[c:11](:[c:12])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | Methyl 3-(5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (1.60 g, 42%) in the same manner as described in the above example 5 (1) from methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (2.00 g, 10.57 mmol) and 4-nitrophthalic anhydride (0.57 g, 3.43 mmol), and... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | COC(=O)C(CN)C1(C)OCCO1.O=C1OC(=O)c2cc([N+](=O)[O-])ccc21>>COC(=O)C(CN1C(=O)c2ccc([N+](=O)[O-])cc2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3fcb315f756a4cc1aaa896443067c62d | COC(=O)C(CN)C1(C)OCCO1.Cc1cccc2c1C(=O)OC2=O>>COC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C1(C)OCCO1 | NCC(C(=O)OC)C1(OCCO1)C.CC1=C2C(C(=O)OC2=O)=CC=C1>>CC1=C2C(N(C(C2=CC=C1)=O)CC(C(=O)OC)C1(OCCO1)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][NH2:7])[C:19]1([CH3:20])[O:21][CH2:22][CH2:23][O:24]1.O1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([CH3:15])[c:16]2[C:17]1=[O:18]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][cH:13][c:14]([CH3:15])[c:16]2[C:17]1=[O:18])[C:19]1([CH3:20])[O:... | COC(=O)C(CN)C1(C)OCCO1.Cc1cccc2c1C(=O)OC2=O | COC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[c:13](:[c:14]):[c:11](:[c:12])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | Methyl 3-(4-methyl-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.39 g, 52%) in the same manner as described in the above example 5 (1) from methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.54 g, 2.86 mmol) and 3-methylphthalic anhydride (0.56 g, 3.44 mmol), an... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | COC(=O)C(CN)C1(C)OCCO1.Cc1cccc2c1C(=O)OC2=O>>COC(=O)C(CN1C(=O)c2cccc(C)c2C1=O)C1(C)OCCO1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-df42ecd09d73439fb486c4a6729824bb | COC(=O)C(CN)C1(C)OCCO1.Cc1ccc2c(c1)C(=O)OC2=O>>COC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C1(C)OCCO1 | NCC(C(=O)OC)C1(OCCO1)C.CC=1C=C2C(C(=O)OC2=O)=CC1>>CC=1C=C2C(N(C(C2=CC1)=O)CC(C(=O)OC)C1(OCCO1)C)=O | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][NH2:7])[C:19]1([CH3:20])[O:21][CH2:22][CH2:23][O:24]1.O1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([CH3:14])[cH:15][c:16]2[C:17]1=[O:18]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][N:7]1[C:8](=[O:9])[c:10]2[cH:11][cH:12][c:13]([CH3:14])[cH:15][c:16]2[C:17]1=[O:18])[C:19]1([CH3:20])[O:... | COC(=O)C(CN)C1(C)OCCO1.Cc1ccc2c(c1)C(=O)OC2=O | COC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C1(C)OCCO1 | null | null | null | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCC1OCCO1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[NH2;D1;+0:6].[O;D1;H0:7]=[C;H0;D3;+0:8]1-O-[C;H0;D3;+0:9](=[O;D1;H0:10])-[c:11](:[c:12]):[c:13]-1:[c:14]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[N;H0;D3;+0:6]1-[C;H0;D3;+0:8](=[O;D1;H0:7])-[c:13](:[c:14]):[c:11](:[c:12])-[C;H0;D3;+0:9]-1=[O;D1;H0:10] | null | [] | null | null | null | null | Methyl 3-(5-methyl-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-(2-methyl-[1,3]dioxolan-2-yl)propionate was prepared (0.12 g, 10%) in the same manner as described in the above example 5 (1) from methyl 3-amino-2-(2-methyl-[1,3]dioxolan-2-yl)propionate (0.50 g, 2.64 mmol) and 4-methylphthalic anhydride (0.56 g, 3.43 mmol), an... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1COCO1 | HO- | null | null | null | COC(=O)C(CN)C1(C)OCCO1.Cc1ccc2c(c1)C(=O)OC2=O>>COC(=O)C(CN1C(=O)c2ccc(C)cc2C1=O)C1(C)OCCO1 |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.