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-c3a75813d0b24864aa4f7cd526efd6aa | ord-1904c867b1b84d10aefb06cd7dec1eac | CCOCC.O=C(Cl)CCCCl.Oc1cccc(F)c1.Oc1ccccc1>>O=C(CCCCl)c1ccc(F)cc1O.O=C(CCCCl)c1ccccc1O | B(F)(F)F.CCOCC.FC=1C=C(C=CC1)O.C1(=CC=CC=C1)O.ClCCCC(=O)Cl>>ClCCCC(=O)C1=C(C=C(C=C1)F)O.ClCCCC(=O)C1=C(C=CC=C1)O | [O:15]([CH2:16][CH3:17])[CH2:19][CH3:18].[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][Cl:6])[Cl:20].[cH:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]1[OH:14].[cH:21]1[cH:22][cH:23][cH:24][cH:25][c:26]1[OH:27]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][Cl:6])[c:7]1[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]1[OH:14].[O:15]=[C:16]([CH2:17][CH2:18]... | CCOCC.O=C(Cl)CCCCl.Oc1cccc(F)c1.Oc1ccccc1 | O=C(CCCCl)c1ccc(F)cc1O.O=C(CCCCl)c1ccccc1O | null | null | null | C-C Coupling | OtherReaction | f6e3f5fae6ba9aa012e548b2c7e7796d55f302a3eb278dd6c088c97d5fcc073e | a8db79155e5f746b7dfdd411e413dcf17b0d00a9bf013adc4221557f79162a3f | c1ccccc1.c1ccccc1 | [CH3;D1;+0:1]-[CH2;D2;+0:2]-[O;H0;D2;+0:3]-[CH2;D2;+0:4]-[CH3;D1;+0:5].[C:6]-[C:7]-[C;H0;D3;+0:8](-[Cl;H0;D1;+0:9])=[O;D1;H0:10].[O;D1;H1:11]-[c:12](:[c:13]):[cH;D2;+0:14]:[c:15]:[c:16].[O;D1;H1:17]-[c:18](:[c:19]):[cH;D2;+0:20]:[c:21]:[c:22]>>[C:6]-[C:7]-[C;H0;D3;+0:8](=[O;D1;H0:10])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c... | null | [] | 130 | CELSIUS | 18 | HOUR | To a cold boron trifluoride etherate (280 mmol) solution was added 3-fluorophenol or phenol (89 mmol) and 4-chlorobutyryl chloride (178 mmol). The resulting solution was stirred at 130° C. for 18 hours. The reaction mixture was cooled and poured into ice water (100 mL). After stirring for 10 minutes, the water mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether | Primary halide.Ketone.Ketone | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | null | null | 130 | 18 | CCOCC.O=C(Cl)CCCCl.Oc1cccc(F)c1.Oc1ccccc1>>O=C(CCCCl)c1ccc(F)cc1O.O=C(CCCCl)c1ccccc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1c9db1114b854c7eb84e757a71c7335f | CN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12.Fc1ccc2c(CCCCl)noc2c1>>CN1CCN2c3c(cccc31)[C@@H]1CN(CCCc3noc4cc(F)ccc34)CC[C@@H]12.Cl | ClCCCC1=NOC2=C1C=CC(=C2)F.CN1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCNC1.N>>Cl.FC1=CC2=C(C(=NO2)CCCN2C[C@@H]3[C@@H](N4CCN(C=5C=CC=C3C45)C)CC2)C=C1 | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]2[c:6]3[c:7]([cH:8][cH:9][cH:10][c:11]31)[C@@H:12]1[CH2:13][NH:14][CH2:28][CH2:29][C@H:30]21.[CH2:15]([CH2:16][CH2:17][c:18]1[n:19][o:20][c:21]2[cH:22][c:23]([F:24])[cH:25][cH:26][c:27]12)[Cl:31]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]2[c:6]3[c:7]([cH:8][cH:9][cH:10][c:11]31)[C@@H:12]1[CH2:13]... | CN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12.Fc1ccc2c(CCCCl)noc2c1 | CN1CCN2c3c(cccc31)[C@@H]1CN(CCCc3noc4cc(F)ccc34)CC[C@@H]12.Cl | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e632fd65463eb262ac3c07c304635f39a39b141a1af7e45d1ba4958b16cbff9a | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc2c3c(c1)[C@@H]1CN(CCCc4noc5ccccc45)CC[C@@H]1N3CCN2 | [C:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:3]-[C:2]-[C:1])-[C:8]-[C:9].[ClH;D0;+0:4] | null | [] | null | null | null | null | The title compound was prepared from addition of 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole from Step D and (6bR,10aS)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline following General procedure A, Example 197. 1H NMR (300 MHz, CDCl3) δ 7.63 (dd, J=8.8 Hz, 4.7 Hz, 1H), 7.20–7.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC[NH]2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | c1ccc2oncc2c1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | null | null | null | null | CN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12.Fc1ccc2c(CCCCl)noc2c1>>CN1CCN2c3c(cccc31)[C@@H]1CN(CCCc3noc4cc(F)ccc34)CC[C@@H]12.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-df231b2eefe7403fa727fe476aa6064d | CN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12.ClCCCc1noc2ccccc12>>CN1CCN2c3c(cccc31)[C@@H]1CN(CCCc3noc4ccccc34)CC[C@@H]12.Cl | ClCCCC1=NOC2=C1C=CC=C2.CN1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCNC1.N>>Cl.O1N=C(C2=C1C=CC=C2)CCCN2C[C@@H]1[C@@H](N3CCN(C=4C=CC=C1C34)C)CC2 | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]2[c:6]3[c:7]([cH:8][cH:9][cH:10][c:11]31)[C@@H:12]1[CH2:13][NH:14][CH2:27][CH2:28][C@H:29]21.[CH2:15]([CH2:16][CH2:17][c:18]1[n:19][o:20][c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]12)[Cl:30]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]2[c:6]3[c:7]([cH:8][cH:9][cH:10][c:11]31)[C@@H:12]1[CH2:13][N:14](... | CN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12.ClCCCc1noc2ccccc12 | CN1CCN2c3c(cccc31)[C@@H]1CN(CCCc3noc4ccccc34)CC[C@@H]12.Cl | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e632fd65463eb262ac3c07c304635f39a39b141a1af7e45d1ba4958b16cbff9a | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc2c3c(c1)[C@@H]1CN(CCCc4noc5ccccc45)CC[C@@H]1N3CCN2 | [C:1]-[C:2]-[CH2;D2;+0:3]-[Cl;H0;D1;+0:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:3]-[C:2]-[C:1])-[C:8]-[C:9].[ClH;D0;+0:4] | null | [] | null | null | null | null | The title compound was prepared from addition 3-(3-chloropropyl)-1,2-benzisoxazole from Step D Example 22 and (6bR,10aS)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline following the General procedure A of Example 197. 1H NMR (300 MHz, CDCl3) δ 7.59–7.62 (m, 1H), 7.46–7.50 (m, 2H... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC[NH]2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | c1ccc2oncc2c1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | null | null | null | null | CN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12.ClCCCc1noc2ccccc12>>CN1CCN2c3c(cccc31)[C@@H]1CN(CCCc3noc4ccccc34)CC[C@@H]12.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d00d1a250cf64390bc55c24d83d3a652 | CCOC(=O)N1CCc2c(c3cccc4c3n2CC(=O)N4)C1>>CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3 | [OH-].[Na+].C(#N)[BH3-].[Na+].O=C1NC=2C=CC=C3C2N(C1)C1=C3CN(CC1)C(=O)OCC.[OH-].[NH4+]>>O=C1NC=2C=CC=C3C2N(C1)[C@@H]1[C@H]3CN(CC1)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][c:9]2[c:10]([c:12]3[cH:13][cH:14][cH:15][c:16]4[c:17]3[n:18]2[CH2:19][C:20](=[O:21])[NH:22]4)[CH2:11]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]3[c:17]1[N:18]2[CH2:19][C:20](=[O:21])[NH:22]3 | CCOC(=O)N1CCc2c(c3cccc4c3n2CC(=O)N4)C1 | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3 | null | null | FC(C(=O)O)(F)F | Reduction | OtherReaction | 6fe5078fa337973e230c6466957c05e6e5e019f7173f54dc2b3cce93e1834287 | 3f9bd1254c561719832bd71149feb4e99c5764db1feb47bf9fbdfb1c414d602b | O=C1CN2c3c(cccc3[C@@H]3CNCC[C@@H]32)N1 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[c;H0;D3;+0:6]2:[c:7](:[c:8]):[c:9]3:[c:10]-[#7:11]-[C:12](=[O;D1;H0:13])-[C:14]-[n;H0;D3;+0:15]:3:[c;H0;D3;+0:16]:2-[C:17]-[C:18]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C@@H;D3;+0:6]2-[C@H;D3;+0:16](-[C:17]-[C:18]-1)-[N;H0;D3;+0:15]1-[C:14]-[C:12](=[O;D1;H0:13])-[#7:11]-[... | 90.3 | [{"value": 90.0, "product": "O=C1NC=2C=CC=C3C2N(C1)[C@@H]1[C@H]3CN(CC1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.3, "product": "O=C1NC=2C=CC=C3C2N(C1)[C@@H]1[C@H]3CN(CC1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Sodium cyanoborohydride (4.0 g, 65 mmol) was added, in small portions, to a vigorously stirred solution of ethyl 2,3,9,10-tetrahydro-2-oxo-1H-pyrido[3′,4′:4,5]-pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (11.97 g, 40 mmol) in trifluoroacetic acid (125 mL) cooled in an ice-water bath, under nitrogen. After the additi... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cc2c3c(c1)c1c(n3CCN2)CC[NH]C1 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | null | FC(C(=O)O)(F)F | null | 0.5 | CCOC(=O)N1CCc2c(c3cccc4c3n2CC(=O)N4)C1>FC(C(=O)O)(F)F>CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-09747b86a1ae4216958fb9948c11d0d9 | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3.CI>>CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3C | [H-].[Na+].O=C1NC=2C=CC=C3C2N(C1)[C@@H]1[C@H]3CN(CC1)C(=O)OCC.IC>>CN1C(CN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCN(C1)C(=O)OCC)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]3[c:17]1[N:18]2[CH2:19][C:20](=[O:21])[NH:22]3.I[CH3:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]3[c:17]1[N:18]2[CH2:19][C:20](=[O:... | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3.CI | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3C | null | null | CCCCCC.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 980d07b89e1a95150d6f8a4b1bb819c09ac2db99776f72555e02c19625afb4f5 | 0a16658309ac5595448433dd7ef49294830b145345df0b202ccd54727262e629 | O=C1CN2c3c(cccc3[C@@H]3CNCC[C@@H]32)N1 | I-[CH3;D1;+0:1].[O;D1;H0:2]=[C:3]1-[C:4]-[#7:5]-[c:6]:[c:7](:[c:8])-[NH;D2;+0:9]-1>>[CH3;D1;+0:1]-[N;H0;D3;+0:9]1-[C:3](=[O;D1;H0:2])-[C:4]-[#7:5]-[c:6]:[c:7]-1:[c:8] | 87 | [{"value": 87.0, "product": "CN1C(CN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCN(C1)C(=O)OCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.9, "product": "CN1C(CN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCN(C1)C(=O)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Sodium hydride (900 mg of 60% dispersion in oil; 22.5 mmol) was washed with hexane, and suspended in anhydrous dimethylformamide (5 mL). The suspension was added to a stirred solution of ethyl (6bR,10aS)-2-oxo-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (6.02 g, 20 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Tertiary amide | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | HI | CCCCCC.CN(C=O)C | null | 1 | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3.CI>CCCCCC.CN(C=O)C>CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4408fc5ded764b36931f251d7cf317fd | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3C>>CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCN3C | B.CN1C(CN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCN(C1)C(=O)OCC)=O.Cl>>CN1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCN(C1)C(=O)OCC | O=[C:20]1[CH2:19][N:18]2[C@H:9]3[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:11][C@H:10]3[c:12]3[cH:13][cH:14][cH:15][c:16]([c:17]32)[N:21]1[CH3:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][C@H:9]2[C@@H:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]3[c:17]1[N:18]2[CH2:19][CH2:20][N:21]3[CH3:... | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3C | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCN3C | null | null | O1CCCC1 | Reduction | Reduction of tertiary amides to amines | b85edbb5fb9a189d3d5456aab7a3bf994122238d91275bcbace6c7a052dc91bc | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCN2 | O=[C;H0;D3;+0:1]1-[C:2]-[#7:3](-[C:4])-[c:5]:[c:6]-[#7:7]-1-[C;D1;H3:8]>>[C:4]-[#7:3]1-[C:2]-[CH2;D2;+0:1]-[#7:7](-[C;D1;H3:8])-[c:6]:[c:5]-1 | 93 | [{"value": 93.0, "product": "CN1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCN(C1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "CN1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCN(C1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of borane in tetrahydrofuran (1M, 33 mL, 33 mmol) was added dropwise to a stirred solution of ethyl (6bR,10aS)-3-methyl-2-oxo-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (5.24 g, 16.6 mmol) in anhydrous tetrahydrofuran (25 mL) under nitrogen. After the additio... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | Other | O1CCCC1 | null | null | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3C>O1CCCC1>CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCN3C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-46d7f2d51615421183cda533e5cd96d7 | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCN3C>>CN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12 | [OH-].[K+].CN1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCN(C1)C(=O)OCC>>CN1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCNC1 | CCOC(=O)[N:14]1[CH2:13][C@H:12]2[c:7]3[c:6]4[c:11]([cH:10][cH:9][cH:8]3)[N:2]([CH3:1])[CH2:3][CH2:4][N:5]4[C@H:17]2[CH2:16][CH2:15]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]2[c:6]3[c:7]([cH:8][cH:9][cH:10][c:11]31)[C@@H:12]1[CH2:13][NH:14][CH2:15][CH2:16][C@H:17]21 | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCN3C | CN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12 | null | null | C(CCC)O | Reduction | Hydrogenolysis of tertiary amines | 64340f7d0b350a19bf30b154f1ce71f378bd544e8fb5c5b6b78431eb1ca1b0d3 | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCN2 | C-C-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 95.1 | [{"value": 95.0, "product": "CN1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCNC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.1, "product": "CN1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCNC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Powdered potassium hydroxide (10.0 g) was added to a stirred solution of ethyl (6bR,10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (4.52 g, 15.0 mmol) in warm 1-butanol (50 mL) and the resulting mixture was heated under reflux for 5 h. It was then evaporated ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC[NH]2 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC[NH]2 | HO- | C(CCC)O | null | null | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCN3C>C(CCC)O>CN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8357a7c9abfa492eb4945ce6cff6b78e | CCI.CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3>>CCN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12 | O=C1NC=2C=CC=C3C2N(C1)[C@@H]1[C@H]3CN(CC1)C(=O)OCC.C(C)I>>C(C)N1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCNC1 | I[CH2:2][CH3:1].CCOC(=O)[N:15]1[CH2:14][C@H:13]2[c:8]3[c:7]4[c:12]([cH:11][cH:10][cH:9]3)[NH:3][C:4](=O)[CH2:5][N:6]4[C@H:18]2[CH2:17][CH2:16]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]2[c:7]3[c:8]([cH:9][cH:10][cH:11][c:12]31)[C@@H:13]1[CH2:14][NH:15][CH2:16][CH2:17][C@H:18]21 | CCI.CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3 | CCN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 260fe71a473b60bc6699adc87a714c283b8e75d0d15e5c63eedaf0773c2c0554 | 5fa8b50dba8178d1bbd9e21cc84d8eae82649eda60ef87b4318bbafd818aae11 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCN2 | C-C-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[C:5]-[C:6]-1)-[#7:7]1-[C:8]-[C;H0;D3;+0:9](=O)-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]-1.I-[CH2;D2;+0:14]-[C;D1;H3:15]>>[C;D1;H3:15]-[CH2;D2;+0:14]-[N;H0;D3;+0:10]1-[CH2;D2;+0:9]-[C:8]-[#7:7](-[c:13]:[c:11]-1:[c:12])-[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | null | null | Utilizing the material from Example 255 Step A, the title compound was prepared in analogous fashion using ethyl iodide as the alkyl halide and following the procedure of Step B–D of Example 255, as a light brown amorphous solid. 1H NMR (CDCl3, 300 MHz) δ 1.15 (t, 3H), 1.70–2.01 (m, 3H), 2.65–2.70 (t, J=9.6 Hz, 3H), 2.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ether.Secondary amide | Secondary amine.Tertiary amine | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC[NH]2 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC[NH]2 | HI | null | null | null | CCI.CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3>>CCN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d2c035a66a65479c9eed8a8bc8c5ee6f | CCCI.CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3>>CCCN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12 | O=C1NC=2C=CC=C3C2N(C1)[C@@H]1[C@H]3CN(CC1)C(=O)OCC.C(CC)I>>C(CC)N1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCNC1 | I[CH2:3][CH2:2][CH3:1].CCOC(=O)[N:16]1[CH2:15][C@H:14]2[c:9]3[c:8]4[c:13]([cH:12][cH:11][cH:10]3)[NH:4][C:5](=O)[CH2:6][N:7]4[C@H:19]2[CH2:18][CH2:17]1>>[CH3:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]2[c:8]3[c:9]([cH:10][cH:11][cH:12][c:13]31)[C@@H:14]1[CH2:15][NH:16][CH2:17][CH2:18][C@H:19]21 | CCCI.CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3 | CCCN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 260fe71a473b60bc6699adc87a714c283b8e75d0d15e5c63eedaf0773c2c0554 | 5fa8b50dba8178d1bbd9e21cc84d8eae82649eda60ef87b4318bbafd818aae11 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCN2 | C-C-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[C:5]-[C:6]-1)-[#7:7]1-[C:8]-[C;H0;D3;+0:9](=O)-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]-1.I-[CH2;D2;+0:14]-[C:15]-[C;D1;H3:16]>>[C;D1;H3:16]-[C:15]-[CH2;D2;+0:14]-[N;H0;D3;+0:10]1-[CH2;D2;+0:9]-[C:8]-[#7:7](-[c:13]:[c:11]-1:[c:12])-[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-... | null | [] | null | null | null | null | Utilizing the material from Example 255 Step A, the title compound was prepared in analogous fashion using propyl iodide as the alkyl halide and following the procedure of Step B–D of Example 255, as an amorphous tan solid. 1H NMR (CDCl3, 300 MHz) δ 0.94 (t, 2H), 1.40–2.01 (m, 6H), 2.65–2.70 (t, J=9.6 Hz, 2H), 2.70–2.9... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ether.Secondary amide | Secondary amine.Tertiary amine | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC[NH]2 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC[NH]2 | HI | null | null | null | CCCI.CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3>>CCCN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a0db3e26d47a4482b8294d3c5d4b1751 | CC(C)I.CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3>>CC(C)N1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12 | O=C1NC=2C=CC=C3C2N(C1)[C@@H]1[C@H]3CN(CC1)C(=O)OCC.C(C)(C)I>>C(C)(C)N1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCNC1 | I[CH:2]([CH3:1])[CH3:3].CCOC(=O)[N:16]1[CH2:15][C@H:14]2[c:9]3[c:8]4[c:13]([cH:12][cH:11][cH:10]3)[NH:4][C:5](=O)[CH2:6][N:7]4[C@H:19]2[CH2:18][CH2:17]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][N:7]2[c:8]3[c:9]([cH:10][cH:11][cH:12][c:13]31)[C@@H:14]1[CH2:15][NH:16][CH2:17][CH2:18][C@H:19]21 | CC(C)I.CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3 | CC(C)N1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 51aba3152c403e3828f480df1c24fd00e01a93b9bef445a427db2a590eb0513e | 4ab0d2871f7ad18e2c7831a2fc2049eb9f2385b09b03e2f3a97a520e61bae71b | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCN2 | C-C-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[C:5]-[C:6]-1)-[#7:7]1-[C:8]-[C;H0;D3;+0:9](=O)-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]-1.I-[CH;D3;+0:14](-[C;D1;H3:15])-[C;D1;H3:16]>>[C;D1;H3:15]-[CH;D3;+0:14](-[C;D1;H3:16])-[N;H0;D3;+0:10]1-[CH2;D2;+0:9]-[C:8]-[#7:7](-[c:13]:[c:11]-1:[c:12])-[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1... | null | [] | null | null | null | null | Utilizing the material from Example 255 Step A, the title compound was prepared in analogous fashion using isopropyl iodide as the alkyl halide and following the procedure of Step B–D of Example 255, as a viscous brown liquid. 1H NMR (CDCl3, 300 MHz) δ 1.18 (d, 6H), 1.60–1.67 (m, 1H), 1.71–1.94 (m, 2H), 2.63–2.75 (m, 2... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Carbamic ester.Ether.Secondary amide | Secondary amine.Tertiary amine | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC[NH]2 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC[NH]2 | HI | null | null | null | CC(C)I.CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3>>CC(C)N1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-acdd2e919cd744928b60cc08194548e8 | CCCCI.CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3>>CCCCN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12 | O=C1NC=2C=CC=C3C2N(C1)[C@@H]1[C@H]3CN(CC1)C(=O)OCC.C(CCC)I>>C(CCC)N1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCNC1 | I[CH2:4][CH2:3][CH2:2][CH3:1].CCOC(=O)[N:17]1[CH2:16][C@H:15]2[c:10]3[c:9]4[c:14]([cH:13][cH:12][cH:11]3)[NH:5][C:6](=O)[CH2:7][N:8]4[C@H:20]2[CH2:19][CH2:18]1>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]2[c:9]3[c:10]([cH:11][cH:12][cH:13][c:14]31)[C@@H:15]1[CH2:16][NH:17][CH2:18][CH2:19][C@H:20]21 | CCCCI.CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3 | CCCCN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 260fe71a473b60bc6699adc87a714c283b8e75d0d15e5c63eedaf0773c2c0554 | 5fa8b50dba8178d1bbd9e21cc84d8eae82649eda60ef87b4318bbafd818aae11 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CCN2 | C-C-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[C:5]-[C:6]-1)-[#7:7]1-[C:8]-[C;H0;D3;+0:9](=O)-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]-1.I-[CH2;D2;+0:14]-[C:15]-[C:16]>>[C:16]-[C:15]-[CH2;D2;+0:14]-[N;H0;D3;+0:10]1-[CH2;D2;+0:9]-[C:8]-[#7:7](-[c:13]:[c:11]-1:[c:12])-[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | null | null | Utilizing the material from Example 255 Step A, the title compound was prepared in analogous fashion using n-butyl iodide as the alkyl halide and following the procedure of Step B–D of Example 255, as a viscous brown liquid. 1H NMR (CDCl3, 300 Mhz) δ 0.95 (t, 3H), 1.30–1.45 (m, 2H), 1.50–1.65 (m, 2H), 1.95–2.15 (m, 2H)... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ether.Secondary amide | Secondary amine.Tertiary amine | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC[NH]2 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC[NH]2 | HI | null | null | null | CCCCI.CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3>>CCCCN1CCN2c3c(cccc31)[C@@H]1CNCC[C@@H]12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-613b4223845d4184ab9b9410adf77fb2 | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3.ICc1ccccc1>>c1ccc(CN2CCN3c4c(cccc42)[C@@H]2CNCC[C@@H]23)cc1 | O=C1NC=2C=CC=C3C2N(C1)[C@@H]1[C@H]3CN(CC1)C(=O)OCC.C(C1=CC=CC=C1)I>>C(C1=CC=CC=C1)N1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCNC1 | CCOC(=O)[N:18]1[CH2:17][C@H:16]2[c:11]3[c:10]4[c:15]([cH:14][cH:13][cH:12]3)[NH:6][C:7](=O)[CH2:8][N:9]4[C@H:21]2[CH2:20][CH2:19]1.I[CH2:5][c:4]1[cH:3][cH:2][cH:1][cH:23][cH:22]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][N:9]3[c:10]4[c:11]([cH:12][cH:13][cH:14][c:15]42)[C@@H:16]2[CH2:17][NH:18][CH2:19][CH2:... | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3.ICc1ccccc1 | c1ccc(CN2CCN3c4c(cccc42)[C@@H]2CNCC[C@@H]23)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 260fe71a473b60bc6699adc87a714c283b8e75d0d15e5c63eedaf0773c2c0554 | 5fa8b50dba8178d1bbd9e21cc84d8eae82649eda60ef87b4318bbafd818aae11 | c1ccc(CN2CCN3c4c(cccc42)[C@@H]2CNCC[C@@H]23)cc1 | C-C-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[C:5]-[C:6]-1)-[#7:7]1-[C:8]-[C;H0;D3;+0:9](=O)-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]-1.I-[CH2;D2;+0:14]-[c:15](:[c:16]):[c:17]>>[c:12]:[c:11]1:[c:13]-[#7:7](-[C:8]-[CH2;D2;+0:9]-[N;H0;D3;+0:10]-1-[CH2;D2;+0:14]-[c:15](:[c:16]):[c:17])-[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-... | null | [] | null | null | null | null | Utilizing the material from Example 255 Step A, the title compound was prepared in analogous fashion using benzyl iodide as the alkyl halide and following the procedure of Step B–D of Example 255, as a viscous liquid. 1H NMR(CDCl3, 300 MHz) δ 1.60–2.0 (m, 2H), 2.55–2.95(m, 4H), 2.95–3.15 (m, 2H), 3.20–3.45 (m, 3H), 4.4... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ether.Secondary amide | Secondary amine.Tertiary amine | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC[NH]2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC[NH]2 | HI | null | null | null | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3.ICc1ccccc1>>c1ccc(CN2CCN3c4c(cccc42)[C@@H]2CNCC[C@@H]23)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0b2e77a8efa445b4910a2f1651cba09e | CN1CCN2c3c(cccc31)[C@H]1CN(CCCC(=O)c3ccc(F)cc3)CC[C@H]12>>CN1CCN2c3c(cccc31)[C@@H]1CN(CCCC(=O)c3ccc(F)cc3)CC[C@@H]12 | CN1CCN2C=3C(=CC=CC13)[C@@H]1[C@H]2CCN(C1)CCCC(=O)C1=CC=C(C=C1)F>>CN1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCN(C1)CCCC(=O)C1=CC=C(C=C1)F | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]2[c:6]3[c:7]([cH:8][cH:9][cH:10][c:11]31)[C@H:12]1[CH2:13][N:14]([CH2:15][CH2:16][CH2:17][C:18](=[O:19])[c:20]3[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]3)[CH2:27][CH2:28][C@@H:29]21>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]2[c:6]3[c:7]([cH:8][cH:9][cH:10][c:11]31)[C@@H:12]1[CH2:13][N:14]([CH2:1... | CN1CCN2c3c(cccc31)[C@H]1CN(CCCC(=O)c3ccc(F)cc3)CC[C@H]12 | CN1CCN2c3c(cccc31)[C@@H]1CN(CCCC(=O)c3ccc(F)cc3)CC[C@@H]12 | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C(CCCN1CC[C@H]2[C@@H](C1)c1cccc3c1N2CCN3)c1ccccc1 | null | null | [] | null | null | null | null | The above compound was resolved into its enantiomers on chiral HPLC column. 4-((6bS,10aR)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone. Viscous tan liquid. [a]D=−36.8° (c=0.886, CHCl3). MS (CI): 394 (M+H+).
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | null | C(Cl)(Cl)Cl | null | null | CN1CCN2c3c(cccc31)[C@H]1CN(CCCC(=O)c3ccc(F)cc3)CC[C@H]12>C(Cl)(Cl)Cl>CN1CCN2c3c(cccc31)[C@@H]1CN(CCCC(=O)c3ccc(F)cc3)CC[C@@H]12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-978cf607a84f46d4982b87aa73d09631 | CN1C(=O)CN2c3c(cc(-c4ccc(Cl)cc4Cl)cc31)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]12>>CN1CCN2c3c(cc(-c4ccc(Cl)cc4Cl)cc31)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]12 | CC=1C=CC=CC1C.C=CCCCCCC.ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CC(N(C3C1)C)=O)[C@@H]1[C@H]2CN(CC1)C(=O)OC(C)(C)C.B.C1CCOC1>>ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CCN(C3C1)C)[C@@H]1[C@H]2CN(CC1)C(=O)OC(C)(C)C | O=[C:3]1[N:2]([CH3:1])[c:19]2[c:6]3[c:7]([cH:8][c:9](-[c:10]4[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]4[Cl:17])[cH:18]2)[C@@H:20]2[CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31][C@@H:32]2[N:5]3[CH2:4]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]2[c:6]3[c:7]([cH:8][c:9](-[c:10]4[cH:11][cH:... | CN1C(=O)CN2c3c(cc(-c4ccc(Cl)cc4Cl)cc31)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]12 | CN1CCN2c3c(cc(-c4ccc(Cl)cc4Cl)cc31)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]12 | null | null | C1CCOC1 | Reduction | Reduction of tertiary amides to amines | b85edbb5fb9a189d3d5456aab7a3bf994122238d91275bcbace6c7a052dc91bc | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCN3)cc1 | O=[C;H0;D3;+0:1]1-[C:2]-[#7:3](-[C:4])-[c:5]:[c:6]-[#7:7]-1-[C;D1;H3:8]>>[C:4]-[#7:3]1-[C:2]-[CH2;D2;+0:1]-[#7:7](-[C;D1;H3:8])-[c:6]:[c:5]-1 | 58 | [{"value": 58.0, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CCN(C3C1)C)[C@@H]1[C@H]2CN(CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.2, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CCN(C3C1)C)[C@@H]1[C@H]2CN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | null | null | null | null | To a solution of tert-butyl (6bR,10aS)-5-(2,4-dichlorophenyl)-3-methyl-2-oxo-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (100 mg, 0.21 mmol) in THF (5.0 mL), BH3-THF (1M in THF) (0.82 mL, 0.82 mmol) was added dropwise. After addition was completed, the resulting reaction... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | Other | C1CCOC1 | null | null | CN1C(=O)CN2c3c(cc(-c4ccc(Cl)cc4Cl)cc31)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]12>C1CCOC1>CN1CCN2c3c(cc(-c4ccc(Cl)cc4Cl)cc31)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9ff34fccf9a40a6b3e88db116cbc8cf | CN1CCN2c3c(cc(-c4ccc(Cl)cc4Cl)cc31)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]12>>CN1CCN2c3c(cc(-c4ccc(Cl)cc4Cl)cc31)[C@@H]1CNCC[C@@H]12 | ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CCN(C3C1)C)[C@@H]1[C@H]2CN(CC1)C(=O)OC(C)(C)C.[OH-].[Na+]>>ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CCN(C3C1)C)[C@@H]1[C@H]2CNCC1 | CC(C)(C)OC(=O)[N:22]1[CH2:21][C@H:20]2[c:7]3[c:6]4[c:19]([cH:18][c:9](-[c:10]5[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]5[Cl:17])[cH:8]3)[N:2]([CH3:1])[CH2:3][CH2:4][N:5]4[C@H:25]2[CH2:24][CH2:23]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]2[c:6]3[c:7]([cH:8][c:9](-[c:10]4[cH:11][cH:12][c:13]([Cl:14])[cH:15][c:16]4[Cl:17])[cH:1... | CN1CCN2c3c(cc(-c4ccc(Cl)cc4Cl)cc31)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]12 | CN1CCN2c3c(cc(-c4ccc(Cl)cc4Cl)cc31)[C@@H]1CNCC[C@@H]12 | null | null | null | Reduction | Boc amine deprotection | c8e9e752815bb790c1e130bdaeff142903f3fdbe5557ab9e7c4e97add5d41c6b | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCN3)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 80 | [{"value": 80.0, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CCN(C3C1)C)[C@@H]1[C@H]2CNCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.6, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CCN(C3C1)C)[C@@H]1[C@H]2CNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The hydrochloride salt of the title compound was prepared from tert-butyl (6bR,10aS)-5-(2,4-dichlorophenyl)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (50 mg) using the deprotection procedures described in Example 275, Step B. The salt formed was free-based wit... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CC[NH]2 | c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC[NH]2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1CNCC[C@@H]1N3CC[NH]2 | HO- | null | null | null | CN1CCN2c3c(cc(-c4ccc(Cl)cc4Cl)cc31)[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@@H]12>>CN1CCN2c3c(cc(-c4ccc(Cl)cc4Cl)cc31)[C@@H]1CNCC[C@@H]12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7284b827a7f341c185594aec89c7eb91 | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CCN3.OB(O)c1ccc(Cl)cc1Cl>>CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CCN3 | BrC=1C=C2C=3N(CCNC3C1)[C@@H]1[C@H]2CN(CC1)C(=O)OC(C)(C)C.ClC1=C(C=CC(=C1)Cl)B(O)O>>ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CCNC3C1)[C@@H]1[C@H]2CN(CC1)C(=O)OC(C)(C)C | Br[c:16]1[cH:15][c:14]2[c:27]3[c:26]([cH:25]1)[NH:31][CH2:30][CH2:29][N:28]3[C@H:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:13][C@H:12]12.OB(O)[c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][c:23]1[Cl:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@H:11]2[C@@... | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CCN3.OB(O)c1ccc(Cl)cc1Cl | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CCN3 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 7e0a80666e22e30220b2f360ec85e8bd8d76adda934c7385240ddcd629f581f2 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)[C@@H]2CNCC[C@@H]2N4CCN3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[#7:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[Cl;D1;H0:11]):[c:12]>>[#7:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[Cl;D1;H0:11]):[c:12]):[c:2]:[c:3] | 61.8 | [{"value": 60.0, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CCNC3C1)[C@@H]1[C@H]2CN(CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.8, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CCNC3C1)[C@@H]1[C@H]2CN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Tert-butyl (6bR,10aS)-5-(2,4-dichlorophenyl)-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (37 mg, 60%) was prepared via coupling of tert-butyl (6bR,10aS)-5-bromo-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (50 mg, 0.13 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | c1ccccc1.c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | HBr.B | null | null | null | CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(Br)cc3c1N2CCN3.OB(O)c1ccc(Cl)cc1Cl>>CC(C)(C)OC(=O)N1CC[C@H]2[C@@H](C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CCN3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-89bcdbe2e2ba44b9afe24a7112355d9b | CC(C)(C)OC(=O)N1CCc2[nH]c3c([N+](=O)[O-])cccc3c2C1>>CC(C)(C)OC(=O)N1CCc2[nH]c3c(N)cccc3c2C1 | [N+](=O)([O-])C1=CC=CC=2C3=C(NC12)CCN(C3)C(=O)OC(C)(C)C>>NC1=CC=CC=2C3=C(NC12)CCN(C3)C(=O)OC(C)(C)C | O=[N+:15]([O-])[c:14]1[c:13]2[nH:12][c:11]3[c:20]([c:19]2[cH:18][cH:17][cH:16]1)[CH2:21][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]3>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[nH:12][c:13]3[c:14]([NH2:15])[cH:16][cH:17][cH:18][c:19]3[c:20]2[CH2:21]1 | CC(C)(C)OC(=O)N1CCc2[nH]c3c([N+](=O)[O-])cccc3c2C1 | CC(C)(C)OC(=O)N1CCc2[nH]c3c(N)cccc3c2C1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2c3c([nH]c2c1)CCNC3 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | 2 | HOUR | To a solution of tert-butyl 6-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (15.6 g, 49.15 mmol) in ethanol (250 mL) was added a spatula tip of 10% Pd/C. The reaction mixture was shaken under a hydrogen atmosphere (15 psi, Parr apparatus) for 2 h. Upon removal from the Parr apparatus, the reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2c3c(nc2c1)CC[N]C3 | Other | [Pd].C(C)O | null | 2 | CC(C)(C)OC(=O)N1CCc2[nH]c3c([N+](=O)[O-])cccc3c2C1>[Pd].C(C)O>CC(C)(C)OC(=O)N1CCc2[nH]c3c(N)cccc3c2C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-64eff7afe50445debf039097bbec1f7c | CC(C)(C)OC(=O)N1CCc2[nH]c3c(N)cccc3c2C1.O=C(Cl)CCCl>>CC(C)(C)OC(=O)N1CCc2[nH]c3c(NC(=O)CCCl)cccc3c2C1 | NC1=CC=CC=2C3=C(NC12)CCN(C3)C(=O)OC(C)(C)C.ClCCC(=O)Cl.C([O-])(O)=O.[Na+]>>ClCCC(=O)NC1=CC=CC=2C3=C(NC12)CCN(C3)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][c:11]2[nH:12][c:13]3[c:14]([NH2:15])[cH:21][cH:22][cH:23][c:24]3[c:25]2[CH2:26]1.Cl[C:16](=[O:17])[CH2:18][CH2:19][Cl:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][c:11]2[nH:12][c:13]3[c:14]([NH:15][C:16](=[O:17])[CH2:18]... | CC(C)(C)OC(=O)N1CCc2[nH]c3c(N)cccc3c2C1.O=C(Cl)CCCl | CC(C)(C)OC(=O)N1CCc2[nH]c3c(NC(=O)CCCl)cccc3c2C1 | null | CN(C)C=1C=CN=CC1 | C1=CC=CC=C1 | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2c3c([nH]c2c1)CCNC3 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8](:[c:9]):[#7;a:10]:[c:11]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8](:[c:9]):[#7;a:10]:[c:11] | 99 | [{"value": 99.0, "product": "ClCCC(=O)NC1=CC=CC=2C3=C(NC12)CCN(C3)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of tert-butyl 6-amino-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (4.62 g, 16.08 mmol) in benzene (100 mL) was added a catalytic amount of DMAP. An inert atmosphere was created and chloropropionyl chloride (2)(1.68 mL) was added dropwise to the reaction mixture. After stirring at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c3c(nc2c1)CC[N]C3 | HCl | CN(C)C=1C=CN=CC1.C1=CC=CC=C1 | null | 0.333333 | CC(C)(C)OC(=O)N1CCc2[nH]c3c(N)cccc3c2C1.O=C(Cl)CCCl>CN(C)C=1C=CN=CC1.C1=CC=CC=C1>CC(C)(C)OC(=O)N1CCc2[nH]c3c(NC(=O)CCCl)cccc3c2C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c2461e898ce941879538b46d3bf81bff | CN1CCN2c3c(cccc31)[C@@H]1CCN(C(=O)OC(C)(C)C)CC[C@@H]12>>CN1CCN2c3c(cccc31)[C@@H]1CCNCC[C@@H]12 | CN1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCN(CC1)C(=O)OC(C)(C)C.[OH-].[Na+]>>CN1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCNCC1 | CC(C)(C)OC(=O)[N:15]1[CH2:14][CH2:13][C@H:12]2[c:7]3[c:6]4[c:11]([cH:10][cH:9][cH:8]3)[N:2]([CH3:1])[CH2:3][CH2:4][N:5]4[C@H:18]2[CH2:17][CH2:16]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]2[c:6]3[c:7]([cH:8][cH:9][cH:10][c:11]31)[C@@H:12]1[CH2:13][CH2:14][NH:15][CH2:16][CH2:17][C@H:18]21 | CN1CCN2c3c(cccc31)[C@@H]1CCN(C(=O)OC(C)(C)C)CC[C@@H]12 | CN1CCN2c3c(cccc31)[C@@H]1CCNCC[C@@H]12 | null | null | [Cl-].[Na+].O.C(Cl)Cl.C(=O)(C(F)(F)F)O | Reduction | Boc amine deprotection | 6b2d5918b1bbb62a1da148ba095b4c22cda264c0445468ade141c385258ecbff | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc2c3c(c1)[C@@H]1CCNCC[C@@H]1N3CCN2 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 104.7 | [{"value": 103.0, "product": "CN1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCNCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.7, "product": "CN1CCN2C=3C(=CC=CC13)[C@H]1[C@@H]2CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | Tert-butyl (6bS,11aS)-3-methyl-2,3,6b,7,8,10,11,11a-octahydro-1H,9H-azepino[4′,5′:4,5]pyrrolo[1,2,3-de]quinoxaline-9-carboxylate (115 mg, 0.33 mmol) was dissolved in 20% TFA (3 mL) in CH2Cl2 at rt. The reaction was stirred at rt for 2.5 hrs. Ice chips were added to the reaction, an then it was basified with 50% NaOH un... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | c1cc2c3c(c1)[C@@H]1CC[NH]CC[C@@H]1N3CC[NH]2 | c1cc2c3c(c1)[C@@H]1CCNCC[C@@H]1N3CC[NH]2 | c1cc2c3c(c1)[C@@H]1CCNCC[C@@H]1N3CC[NH]2 | HO- | [Cl-].[Na+].O.C(Cl)Cl.C(=O)(C(F)(F)F)O | null | 2.5 | CN1CCN2c3c(cccc31)[C@@H]1CCN(C(=O)OC(C)(C)C)CC[C@@H]12>[Cl-].[Na+].O.C(Cl)Cl.C(=O)(C(F)(F)F)O>CN1CCN2c3c(cccc31)[C@@H]1CCNCC[C@@H]12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-052d77e5abfc477fb5ee178b23b92fe0 | CN1CCN2c3c(cccc31)C1CCNCCC12.O=C(CCCCl)c1ccc(F)cc1>>CN1CCN2c3c(cccc31)C1CCN(CCCC(=O)c3ccc(F)cc3)CCC12 | CN1CCN2C=3C(=CC=CC13)C1C2CCNCC1.ClCCCC(=O)C1=CC=C(C=C1)F.CCN(C(C)C)C(C)C>>CN1CCN2C=3C(=CC=CC13)C1C2CCN(CC1)CCCC(=O)C1=CC=C(C=C1)F | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]2[c:6]3[c:7]([cH:8][cH:9][cH:10][c:11]31)[CH:12]1[CH2:13][CH2:14][NH:15][CH2:28][CH2:29][CH:30]21.Cl[CH2:16][CH2:17][CH2:18][C:19](=[O:20])[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]2[c:6]3[c:7]([cH:8][cH:9][cH:10][c:11]31)[CH:12]1[CH2:13][CH2:14]... | CN1CCN2c3c(cccc31)C1CCNCCC12.O=C(CCCCl)c1ccc(F)cc1 | CN1CCN2c3c(cccc31)C1CCN(CCCC(=O)c3ccc(F)cc3)CCC12 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 78309cea36c4b57c3488d59cbc25b7f0249d7382f00d475ecdfbc90c1ee4feca | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CCC2c3cccc4c3N(CCN4)C2CC1)c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[O;D1;H0:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[O;D1;H0:5])-[C:9]-[C:10] | 31 | [{"value": 31.0, "product": "CN1CCN2C=3C(=CC=CC13)C1C2CCN(CC1)CCCC(=O)C1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.7, "product": "CN1CCN2C=3C(=CC=CC13)C1C2CCN(CC1)CCCC(=O)C1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 96 | CELSIUS | 18 | HOUR | 3-Methyl-2,3,7,8,9,10,11,11a-octahydro-1H,6bH-azepino[4′,5′:4,5]pyrrolo[1,2,3-de]quinoxaline (72 mg, 0.3 mmol), 4-chloro-4′-flourobutyrophenone (119 mg, 0.6 mmol), KI (49 mg, 0.3 mmol), and DIEA (383 mg, 3 mmol) were added to dioxane (2.5 mL). The suspension was stirred at 96° C. for 18 hrs. The reaction was cooled to ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)C1CCNCCC1N3CC[NH]2 | c1cc2c3c(c1)C1CC[NH]CCC1N3CC[NH]2 | c1ccccc1.c1cc2c3c(c1)C1CC[NH]CCC1N3CC[NH]2 | HCl | O1CCOCC1 | 96 | 18 | CN1CCN2c3c(cccc31)C1CCNCCC12.O=C(CCCCl)c1ccc(F)cc1>O1CCOCC1>CN1CCN2c3c(cccc31)C1CCN(CCCC(=O)c3ccc(F)cc3)CCC12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cf8e8b15a9a04ebea52f5a2bf85cca00 | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3.CI>>CCOC(=O)N1CCc2c(c3cccc4c3n2C(C)(C)C(=O)N4C)C1 | O=C1NC=2C=CC=C3C2N(C1)[C@@H]1[C@H]3CN(CC1)C(=O)OCC.[H-].[Na+].CI.CN(C)C=O>>CC1(C(N(C=2C=CC=C3C2N1C1=C3CN(CC1)C(=O)OCC)C)=O)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][C@H:9]2[C@H:10]([c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[N:17]2[CH2:18][C:21](=[O:22])[NH:23]4)[CH2:25]1.I[CH3:24]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][c:9]2[c:10]([c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[n:17]2[C:18]([CH3:19])([CH3:20])[C:21](=[... | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3.CI | CCOC(=O)N1CCc2c(c3cccc4c3n2C(C)(C)C(=O)N4C)C1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 752a8786c40f1841769d3c150929e814462d11724e0dd540f9edf1f45e586905 | 8c44445309ae5ab70d1a3b7f1a9d955e701b46095afe5c0bf4042a19b519dbd1 | O=C1Cn2c3c(c4cccc(c42)N1)CNCC3 | I-[CH3;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[#7:5]1-[C:6]-[C@@H;D3;+0:7]2-[C@H;D3;+0:8](-[C:9]-[C:10]-1)-[N;H0;D3;+0:11]1-[CH2;D2;+0:12]-[C:13](=[O;D1;H0:14])-[NH;D2;+0:15]-[c:16](:[c:17]):[c:18]-1:[c:19]-2:[c:20]>>[#8:2]-[C:3](=[O;D1;H0:4])-[#7:5]1-[C:6]-[c;H0;D3;+0:7]2:[c:19](:[c:20]):[c:18]3:[c:16](:[c:17])-[N;H0;D3;... | 90 | [{"value": 90.0, "product": "CC1(C(N(C=2C=CC=C3C2N1C1=C3CN(CC1)C(=O)OCC)C)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 6 | HOUR | To a solution of ethyl 2-oxo-2,3,9,10-tetrahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (from Example 211, Step A) (360 mg, 1.2 mmol) in DMF (20 mL) at rt was added NaH (172 mg, 4.8 mmol), MeI (0.25 mL, 4.0 mmol) and stirred at 25° C. for 6 hours. The solution was diluted with water (30 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Tertiary amine | Tertiary amide | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | c1cc2c3c(c1)c1c(n3CC[NH]2)CC[NH]C1 | c1cc2c3c(c1)c1c(n3CC[NH]2)CC[NH]C1 | I- | O | 25 | 6 | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3.CI>O>CCOC(=O)N1CCc2c(c3cccc4c3n2C(C)(C)C(=O)N4C)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2e890b6654fc4022af6146dc53482ebb | CCOC(=O)N1CCc2c(c3cccc4c3n2C(C)(C)C(=O)N4C)C1>>CCOC(=O)N1CCc2c(c3cccc4c3n2C(C)(C)CN4C)C1 | CC1(C(N(C=2C=CC=C3C2N1C1=C3CN(CC1)C(=O)OCC)C)=O)C.Cl.O>>C(C)OC(=O)N1CC2=C(N3C(CN(C=4C=CC=C2C34)C)(C)C)CC1 | O=[C:21]1[C:18]([CH3:19])([CH3:20])[n:17]2[c:9]3[c:10]([c:11]4[cH:12][cH:13][cH:14][c:15]([c:16]42)[N:22]1[CH3:23])[CH2:24][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH2:8]3>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][c:9]2[c:10]([c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[n:17]2[C:18]([CH3:19])([CH3:20])[... | CCOC(=O)N1CCc2c(c3cccc4c3n2C(C)(C)C(=O)N4C)C1 | CCOC(=O)N1CCc2c(c3cccc4c3n2C(C)(C)CN4C)C1 | null | null | C1CCOC1 | Reduction | Reduction of tertiary amides to amines | 5fa3a89ad4a5f755ae33c982f253a7fc08686eefa0997651ea69b1e0b6f3df23 | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | c1cc2c3c(c1)c1c(n3CCN2)CCNC1 | O=[C;H0;D3;+0:1]1-[#7:2](-[C;D1;H3:3])-[c:4]:[c:5]:[#7;a:6](:[c:7])-[C:8]-1(-[C;D1;H3:9])-[C;D1;H3:10]>>[C;D1;H3:9]-[C:8]1(-[C;D1;H3:10])-[CH2;D2;+0:1]-[#7:2](-[C;D1;H3:3])-[c:4]:[c:5]:[#7;a:6]-1:[c:7] | 66.3 | [{"value": 66.0, "product": "C(C)OC(=O)N1CC2=C(N3C(CN(C=4C=CC=C2C34)C)(C)C)CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.3, "product": "C(C)OC(=O)N1CC2=C(N3C(CN(C=4C=CC=C2C34)C)(C)C)CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 5 | HOUR | To a solution of ethyl 1,1,3-trimethyl-2-oxo-2,3,9,10-tetrahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (240 mg, 0.7 mmol) in THF (20 mL) at 25° C. was added BH3/THF complex (0.7 mL, 0.7 mmol). The mixture was stirred at 80° C. for 5 hours then cooled to rt and added 6N HCl (10 mL) with stir... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | c1cc2c3c(c1)c1c(n3CC[NH]2)CC[NH]C1 | c1cc2c3c(c1)c1c(n3CC[NH]2)CC[NH]C1 | c1cc2c3c(c1)c1c(n3CC[NH]2)CC[NH]C1 | Other | C1CCOC1 | 80 | 5 | CCOC(=O)N1CCc2c(c3cccc4c3n2C(C)(C)C(=O)N4C)C1>C1CCOC1>CCOC(=O)N1CCc2c(c3cccc4c3n2C(C)(C)CN4C)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-839480f60904490981a35ec588a9f443 | CCOC(=O)N1CCc2c(c3cccc4c3n2C(C)(C)CN4C)C1>>CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(C)(C)CN3C | C(C)OC(=O)N1CC2=C(N3C(CN(C=4C=CC=C2C34)C)(C)C)CC1.[BH3-]C#N.[Na+]>>C(C)OC(=O)N1CC2C(N3C(CN(C=4C=CC=C2C34)C)(C)C)CC1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][c:9]2[c:10]([c:12]3[cH:13][cH:14][cH:15][c:16]4[c:17]3[n:18]2[C:19]([CH3:20])([CH3:21])[CH2:22][N:23]4[CH3:24])[CH2:11]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]2[CH:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]3[c:17]1[N:18]2[C:19]([CH3:20])([C... | CCOC(=O)N1CCc2c(c3cccc4c3n2C(C)(C)CN4C)C1 | CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(C)(C)CN3C | null | null | C(=O)(C(F)(F)F)O | Reduction | OtherReaction | 340cf53908efa49cc662c219bf9df412f1d128f5373473fd3c1f2437e4111407 | 3f9bd1254c561719832bd71149feb4e99c5764db1feb47bf9fbdfb1c414d602b | c1cc2c3c(c1)C1CNCCC1N3CCN2 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[c;H0;D3;+0:6]2:[c:7](:[c:8]):[c:9]3:[c:10]-[#7:11]-[C:12]-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[n;H0;D3;+0:16]:3:[c;H0;D3;+0:17]:2-[C:18]-[C:19]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[CH;D3;+0:6]2-[CH;D3;+0:17](-[C:18]-[C:19]-1)-[N;H0;D3;+0:16]1-[c:9](:[c:10]-[#7:11]-[C:1... | null | [] | null | null | 4 | HOUR | To a solution of ethyl-1,1,3-trimethyl-2,3,9,10-tetrahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (69 mg, 0.21 mmol) in TFA (2 mL) at 0° C. was added NaBH3CN (53 mg, 0.84 mmol). The mixture was stirred at rt for 4 hours, and then removed the TFA by N2. About 10 mL of H2O was added and then w... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cc2c3c(c1)c1c(n3CC[NH]2)CC[NH]C1 | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | null | C(=O)(C(F)(F)F)O | null | 4 | CCOC(=O)N1CCc2c(c3cccc4c3n2C(C)(C)CN4C)C1>C(=O)(C(F)(F)F)O>CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(C)(C)CN3C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c32e62ca360e4113b29284295ba445c8 | CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(C)(C)CN3C>>CN1CC(C)(C)N2c3c(cccc31)C1CNCCC12 | CC1(CN(C=2C=CC=C3C2N1C1C3CN(CC1)C(=O)OCC)C)C.[OH-].[K+]>>CC1(CN(C=2C=CC=C3C2N1C1C3CNCC1)C)C | CCOC(=O)[N:16]1[CH2:15][CH:14]2[c:9]3[c:8]4[c:13]([cH:12][cH:11][cH:10]3)[N:2]([CH3:1])[CH2:3][C:4]([CH3:5])([CH3:6])[N:7]4[CH:19]2[CH2:18][CH2:17]1>>[CH3:1][N:2]1[CH2:3][C:4]([CH3:5])([CH3:6])[N:7]2[c:8]3[c:9]([cH:10][cH:11][cH:12][c:13]31)[CH:14]1[CH2:15][NH:16][CH2:17][CH2:18][CH:19]21 | CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(C)(C)CN3C | CN1CC(C)(C)N2c3c(cccc31)C1CNCCC12 | null | null | O.C(CCC)O | Reduction | Hydrogenolysis of tertiary amines | f02ea03182ae60dba06bafd552caf7571f18d68abb977b141f1d2eed23563f1d | 20c36f41eeb07c3ba4437b51ba72e8ff3c22d0b27e7197b0e9af3127f331149f | c1cc2c3c(c1)C1CNCCC1N3CCN2 | C-C-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 97.1 | [{"value": 81.0, "product": "CC1(CN(C=2C=CC=C3C2N1C1C3CNCC1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.1, "product": "CC1(CN(C=2C=CC=C3C2N1C1C3CNCC1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 20 | HOUR | To a solution of ethyl 1,1,3-trimethyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (8 mg, 0.02 mmol) in n-butanol (5 mL) at rt was added KOH (50 mg, 0.89 mmol) and stirred at 120° C. for 20 hours. The solution was diluted with water (10 mL) and extracted with EtOAc (2×20... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Secondary amine | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | c1cc2c3c(c1)C1CNCCC1N3CC[NH]2 | c1cc2c3c(c1)C1CNCCC1N3CC[NH]2 | HO- | O.C(CCC)O | 120 | 20 | CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(C)(C)CN3C>O.C(CCC)O>CN1CC(C)(C)N2c3c(cccc31)C1CNCCC12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-38abd261a10a4ad5a41e06e9071cc622 | CN1CC(C)(C)N2c3c(cccc31)C1CNCCC12.O=C(CCCCl)c1ccc(F)cc1>>CN1CC(C)(C)N2c3c(cccc31)C1CN(CCCC(=O)c3ccc(F)cc3)CCC12 | CC1(CN(C=2C=CC=C3C2N1C1C3CNCC1)C)C.ClCCCC(=O)C1=CC=C(C=C1)F.C(=O)([O-])[O-].[K+].[K+]>>FC1=CC=C(C=C1)C(CCCN1CC2C(N3C(CN(C=4C=CC=C2C34)C)(C)C)CC1)=O | [CH3:1][N:2]1[CH2:3][C:4]([CH3:5])([CH3:6])[N:7]2[c:8]3[c:9]([cH:10][cH:11][cH:12][c:13]31)[CH:14]1[CH2:15][NH:16][CH2:29][CH2:30][CH:31]21.Cl[CH2:17][CH2:18][CH2:19][C:20](=[O:21])[c:22]1[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]1>>[CH3:1][N:2]1[CH2:3][C:4]([CH3:5])([CH3:6])[N:7]2[c:8]3[c:9]([cH:10][cH:11][cH:12][c:13... | CN1CC(C)(C)N2c3c(cccc31)C1CNCCC12.O=C(CCCCl)c1ccc(F)cc1 | CN1CC(C)(C)N2c3c(cccc31)C1CN(CCCC(=O)c3ccc(F)cc3)CCC12 | null | null | O1CCOCC1.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 54f03545a14958e98f0e3ee8166420a409e56e78b56c8c4176a28619af3af9b3 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCCN1CCC2C(C1)c1cccc3c1N2CCN3)c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[O;D1;H0:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]=[O;D1;H0:5])-[C:9]-[C:10] | 43 | [{"value": 43.0, "product": "FC1=CC=C(C=C1)C(CCCN1CC2C(N3C(CN(C=4C=CC=C2C34)C)(C)C)CC1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.0, "product": "FC1=CC=C(C=C1)C(CCCN1CC2C(N3C(CN(C=4C=CC=C2C34)C)(C)C)CC1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 24 | HOUR | To a solution of 1,1,3-trimethyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline (from Example 283) (82 mg, 0.32 mmol) in dioxane (10 mL) at rt was added 4-chloro-1-(4-fluorophenyl)butan-1-one (83 mg, 0.42 mmol), K2CO3 (100 mg), KI (30 mg) and stirred at 25° C. for 24 hours. The solution ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | c1cc2c3c(c1)C1CNCCC1N3CC[NH]2 | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | c1ccccc1.c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | HCl | O1CCOCC1.O | 25 | 24 | CN1CC(C)(C)N2c3c(cccc31)C1CNCCC12.O=C(CCCCl)c1ccc(F)cc1>O1CCOCC1.O>CN1CC(C)(C)N2c3c(cccc31)C1CN(CCCC(=O)c3ccc(F)cc3)CCC12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b9ca7c7471ad47b7a02b8cc327b4d882 | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3.CI.CN(C)C=O>>CCOC(=O)N1CCc2c(c3cccc4c3n2C(C)C(=O)N4C)C1 | O=C1NC=2C=CC=C3C2N(C1)[C@@H]1[C@H]3CN(CC1)C(=O)OCC.[H-].[Na+].CI.CN(C)C=O>>CC1C(N(C=2C=CC=C3C2N1C1=C3CN(CC1)C(=O)OCC)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][C@H:9]2[C@H:10]([c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[N:17]2[CH2:18][C:20](=[O:21])[NH:22]4)[CH2:24]1.I[CH3:19].CN(C=O)[CH3:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][c:9]2[c:10]([c:11]3[cH:12][cH:13][cH:14][c:15]4[c:16]3[n:17]2[CH:18]([CH3:19])[C... | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3.CI.CN(C)C=O | CCOC(=O)N1CCc2c(c3cccc4c3n2C(C)C(=O)N4C)C1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 075d82b4553c6e43466d8f93081af660d16d95e41691a0a0b207cf8665b828b7 | 6e2a0303410aaf9252fae4e16a65d95bbe41a60005164311b105893830bea4a6 | O=C1Cn2c3c(c4cccc(c42)N1)CNCC3 | C-N(-[CH3;D1;+0:1])-C=O.I-[CH3;D1;+0:2].[#8:3]-[C:4](=[O;D1;H0:5])-[#7:6]1-[C:7]-[C@@H;D3;+0:8]2-[C@H;D3;+0:9](-[C:10]-[C:11]-1)-[N;H0;D3;+0:12]1-[CH2;D2;+0:13]-[C:14](=[O;D1;H0:15])-[NH;D2;+0:16]-[c:17](:[c:18]):[c:19]-1:[c:20]-2:[c:21]>>[#8:3]-[C:4](=[O;D1;H0:5])-[#7:6]1-[C:7]-[c;H0;D3;+0:8]2:[c:20](:[c:21]):[c:19]3:... | 64 | [{"value": 64.0, "product": "CC1C(N(C=2C=CC=C3C2N1C1=C3CN(CC1)C(=O)OCC)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 3 | HOUR | To a solution of ethyl 2-oxo-2,3,9,10-tetrahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (from Example 211, Step A) (500 mg, 1.6 mmol) in DMF (20 mL) at rt was added NaH (147 mg, 3.6 mmol), MeI (0.25 mL, 4.0 mmol) and stirred at 25° C. for 3 hours. The solution was diluted with water (30 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Tertiary amide.Tertiary amine | Tertiary amide | c1cc2c3c(c1)[C@@H]1C[NH]CC[C@@H]1N3CCN2 | c1cc2c3c(c1)c1c(n3CC[NH]2)CC[NH]C1 | c1cc2c3c(c1)c1c(n3CC[NH]2)CC[NH]C1 | HI | O | 25 | 3 | CCOC(=O)N1CC[C@H]2[C@@H](C1)c1cccc3c1N2CC(=O)N3.CI.CN(C)C=O>O>CCOC(=O)N1CCc2c(c3cccc4c3n2C(C)C(=O)N4C)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-da2acf2b79e44ac089ddfca403fc215e | CC(C)(C)OC(=O)N1CCc2[nH]c3c(N)cccc3c2C1.CCOC(=O)Cl>>CCOC(=O)Nc1cccc2c3c([nH]c12)CCN(C(=O)OC(C)(C)C)C3 | NC1=CC=CC=2C3=C(NC12)CCN(C3)C(=O)OC(C)(C)C.C(=O)([O-])[O-].[K+].[K+].ClC(=O)OCC>>C(C)OC(=O)NC1=CC=CC=2C3=C(NC12)CCN(C3)C(=O)OC(C)(C)C | [NH2:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]3[c:13]([nH:14][c:15]12)[CH2:16][CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26]3.Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]3[c:13]([nH:14][c:15]12)[CH2:16][CH2:17][N:18]([C:... | CC(C)(C)OC(=O)N1CCc2[nH]c3c(N)cccc3c2C1.CCOC(=O)Cl | CCOC(=O)Nc1cccc2c3c([nH]c12)CCN(C(=O)OC(C)(C)C)C3 | null | null | O.C(Cl)Cl | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccc2c3c([nH]c2c1)CCNC3 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8](:[c:9]):[#7;a:10]:[c:11]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8](:[c:9]):[#7;a:10]:[c:11] | 605.1 | [{"value": 100.0, "product": "C(C)OC(=O)NC1=CC=CC=2C3=C(NC12)CCN(C3)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 605.1, "product": "C(C)OC(=O)NC1=CC=CC=2C3=C(NC12)CCN(C3)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | 0.5 | HOUR | To a solution of tert-butyl 6-amino-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (7 g, 24.3 mmol) in CH2Cl2 (40 mL) at rt was added saturated K2CO3 (30 mL), ethyl chloroformate (2.4 mL, 4.0 mmol) and stirred at 25° C. for 0.5 hour. The solution was diluted with water (30 mL) and extracted with CH2Cl2 (2×30 m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccc2c3c([nH]c2c1)CC[NH]C3 | HCl | O.C(Cl)Cl | 25 | 0.5 | CC(C)(C)OC(=O)N1CCc2[nH]c3c(N)cccc3c2C1.CCOC(=O)Cl>O.C(Cl)Cl>CCOC(=O)Nc1cccc2c3c([nH]c12)CCN(C(=O)OC(C)(C)C)C3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5401a6a99e0e4a08b9bdab2e0357f4c7 | CCOC(=O)Cl.CCOC(=O)Nc1cccc2c3c([nH]c12)CCN(C(=O)OC(C)(C)C)C3>>CCOC(=O)Nc1cccc2c3c([nH]c12)CCN(C(=O)OCC)C3 | ClC(=O)OCC.C(=O)([O-])[O-].[K+].[K+].C(C)OC(=O)NC1=CC=CC=2C3=C(NC12)CCN(C3)C(=O)OC(C)(C)C.C(=O)(C(F)(F)F)O>>C(C)OC(=O)NC1=CC=CC=2C3=C(NC12)CCN(C3)C(=O)OCC | Cl[C:19](=[O:20])[O:21][CH2:22][CH3:23].CC(C)(C)OC(=O)[N:18]1[CH2:17][CH2:16][c:13]2[c:12]([c:11]3[cH:10][cH:9][cH:8][c:7]([NH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:15]3[nH:14]2)[CH2:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]3[c:13]([nH:14][c:15]12)[CH2:16][CH2:17][N:18]([C:19](=... | CCOC(=O)Cl.CCOC(=O)Nc1cccc2c3c([nH]c12)CCN(C(=O)OC(C)(C)C)C3 | CCOC(=O)Nc1cccc2c3c([nH]c12)CCN(C(=O)OCC)C3 | null | null | O.C(Cl)Cl | Protection | OtherReaction | 0b45546f23ba96b2930821b82e0dc65795a0b0f131fefb23e532431874dc4e69 | 1a97805f72f7ff675aa3cc1da2d0cb1ed8f477704da937465d3c1e9310f62c42 | c1ccc2c3c([nH]c2c1)CCNC3 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[c:4](:[#7;a:5]):[c:6]-[C:7]-1.Cl-[C;H0;D3;+0:8](=[O;D1;H0:9])-[#8:10]-[C:11]>>[#7;a:5]:[c:4]1:[c:6]-[C:7]-[N;H0;D3;+0:1](-[C;H0;D3;+0:8](=[O;D1;H0:9])-[#8:10]-[C:11])-[C:2]-[C:3]-1 | 67 | [{"value": 67.0, "product": "C(C)OC(=O)NC1=CC=CC=2C3=C(NC12)CCN(C3)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.9, "product": "C(C)OC(=O)NC1=CC=CC=2C3=C(NC12)CCN(C3)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of tert-butyl 6-[(ethoxycarbonyl)amino]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (8.7 g, 24.3 mmol) in CH2Cl2 (40 mL) at rt was added TFA (20 mL) and stirred at rt for 3 hours before the solvent was removed by the nitrogen stream. The solution was diluted with water (30 mL) and extracted wi... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carbamic ester.Ether.Ether.Boc | Carbamic ester | c1ccc2c3c(nc2c1)CC[N]C3 | c1ccc2c3c([nH]c2c1)CC[NH]C3 | c1ccc2c3c([nH]c2c1)CC[NH]C3 | HCl | O.C(Cl)Cl | null | 3 | CCOC(=O)Cl.CCOC(=O)Nc1cccc2c3c([nH]c12)CCN(C(=O)OC(C)(C)C)C3>O.C(Cl)Cl>CCOC(=O)Nc1cccc2c3c([nH]c12)CCN(C(=O)OCC)C3 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b5dd63660d0e4d47aea531cdc0d821dc | CCOC(=O)Nc1cccc2c3c([nH]c12)CCN(C(=O)OCC)C3>>CCOC(=O)Nc1cccc2c1NC1CCN(C(=O)OCC)CC21 | [BH3-]C#N.[Na+].C(C)OC(=O)NC1=CC=CC=2C3=C(NC12)CCN(C3)C(=O)OCC.C(=O)(C(F)(F)F)O>>C(C)OC(=O)NC1=CC=CC=2C3C(NC12)CCN(C3)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[nH:13][c:14]1[c:24]2[CH2:23][N:17]([C:18](=[O:19])[O:20][CH2:21][CH3:22])[CH2:16][CH2:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]1[NH:13][CH:14]1[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][CH2:21][CH3:2... | CCOC(=O)Nc1cccc2c3c([nH]c12)CCN(C(=O)OCC)C3 | CCOC(=O)Nc1cccc2c1NC1CCN(C(=O)OCC)CC21 | null | null | C(Cl)Cl | Reduction | OtherReaction | 07e512b90926111428bf112878dcfee6a9f535bae28cf741b34bf997102c8ce2 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | c1ccc2c(c1)NC1CCNCC21 | [#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[c;H0;D3;+0:7]2:[nH;D2;+0:8]:[c:9](:[c:10]):[c:11](:[c:12]):[c;H0;D3;+0:13]:2-[C:14]-1>>[#8:1]-[C:2](=[O;D1;H0:3])-[#7:4]1-[C:5]-[C:6]-[CH;D3;+0:7]2-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11](:[c:12])-[CH;D3;+0:13]-2-[C:14]-1 | 80 | [{"value": 80.0, "product": "C(C)OC(=O)NC1=CC=CC=2C3C(NC12)CCN(C3)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.4, "product": "C(C)OC(=O)NC1=CC=CC=2C3C(NC12)CCN(C3)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of ethyl 6-[(ethoxycarbonyl)amino]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (4.5 g, 13.6 mmol) in CH2Cl2 (40 mL) at 0° C. was added TFA (20 mL) followed by NaCNBH3 (1.8 g, 27 mmol) and stirred at rt for 3 hours before the solvent was removed by the nitrogen stream. To the resulting residue ... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccc2c3c([nH]c2c1)CC[NH]C3 | c1ccc2c(c1)NC1CC[NH]CC21 | c1ccc2c(c1)NC1CC[NH]CC21 | null | C(Cl)Cl | null | 3 | CCOC(=O)Nc1cccc2c3c([nH]c12)CCN(C(=O)OCC)C3>C(Cl)Cl>CCOC(=O)Nc1cccc2c1NC1CCN(C(=O)OCC)CC21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-965cab1df3be4aa384b2495fed28e350 | CC(=O)Cl.CCOC(=O)Nc1cccc2c1NC1CCN(C(=O)OCC)CC21>>CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(=O)CN3C(=O)OCC | C(C)OC(=O)NC1=CC=CC=2C3C(NC12)CCN(C3)C(=O)OCC.[H-].[Na+].C(C)(=O)Cl>>O=C1CN(C=2C=CC=C3C2N1C1C3CN(CC1)C(=O)OCC)C(=O)OCC | Cl[C:19](=[O:20])[CH3:21].[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]2[CH:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]([NH:22][C:23](=[O:24])[O:25][CH2:26][CH3:27])[c:17]1[NH:18]2>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]2[CH:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]3[c:17]1[... | CC(=O)Cl.CCOC(=O)Nc1cccc2c1NC1CCN(C(=O)OCC)CC21 | CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(=O)CN3C(=O)OCC | null | CN(C)C=1C=CN=CC1 | O.CN(C)C=O | Protection | OtherReaction | 32014f139d819d2eb766744258916273133b72bd014f22f00008a52addcf3b2a | 1f98e4cf360ae4d501c8d71883b10df7f5adca46d6ffb377b7d7efe4e9374988 | O=C1CNc2cccc3c2N1C1CCNCC31 | Cl-[C;H0;D3;+0:1](-[CH3;D1;+0:2])=[O;D1;H0:3].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11]1:[c:12]-[C:13]-[C:14](-[C:15])-[NH;D2;+0:16]-1>>[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[N;H0;D3;+0:8]1-[CH2;D2;+0:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:16]2-[C:14](-[C:15])-[C:13]-[c:12]:[c:11]-2:[c:9]-1:[c... | 57 | [{"value": 57.0, "product": "O=C1CN(C=2C=CC=C3C2N1C1C3CN(CC1)C(=O)OCC)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.6, "product": "O=C1CN(C=2C=CC=C3C2N1C1C3CN(CC1)C(=O)OCC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of ethyl 6-[(ethoxycarbonyl)amino]-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate (2.2 g, 6.6 mmol) in DMF (20 mL) at 0° C. was added NaH (660 mg, 16.5 mmol), DMAP (878 mg, 7.2 mmol), acetyl chloride (0.6 mL, 7.2 mmol) and stirred at rt for 16 hours. The solution was diluted with water (30 m... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carbamic ester.Secondary amine | Carbamic ester.Tertiary amide | c1ccc2c(c1)NC1CC[NH]CC21 | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | HCl | CN(C)C=1C=CN=CC1.O.CN(C)C=O | null | 16 | CC(=O)Cl.CCOC(=O)Nc1cccc2c1NC1CCN(C(=O)OCC)CC21>CN(C)C=1C=CN=CC1.O.CN(C)C=O>CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(=O)CN3C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1a37fbcebbb44045bf6f587865e2f566 | CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(=O)CN3C(=O)OCC.CI>>CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(=O)C(C)N3C(=O)OCC | O=C1CN(C=2C=CC=C3C2N1C1C3CN(CC1)C(=O)OCC)C(=O)OCC.[H-].[Na+].CI>>CC1N(C=2C=CC=C3C2N(C1=O)C1C3CN(CC1)C(=O)OCC)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]2[CH:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]3[c:17]1[N:18]2[C:19](=[O:20])[CH2:21][N:23]3[C:24](=[O:25])[O:26][CH2:27][CH3:28].I[CH3:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]2[CH:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]3[c:... | CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(=O)CN3C(=O)OCC.CI | CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(=O)C(C)N3C(=O)OCC | null | null | O.CN(C)C=O | C-C Coupling | Methylation with MeI_secondary | 4e21c68c501a921c07db7be1b7940189d2eecde770dc3a568d774b11bef01893 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C1CNc2cccc3c2N1C1CCNCC31 | I-[CH3;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[#7:5]1-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#7:9](-[C:10])-[c:11]:[c:12]-1>>[#8:2]-[C:3](=[O;D1;H0:4])-[#7:5]1-[c:12]:[c:11]-[#7:9](-[C:10])-[C:7](=[O;D1;H0:8])-[CH;D3;+0:6]-1-[CH3;D1;+0:1] | 80 | [{"value": 80.0, "product": "CC1N(C=2C=CC=C3C2N(C1=O)C1C3CN(CC1)C(=O)OCC)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.8, "product": "CC1N(C=2C=CC=C3C2N(C1=O)C1C3CN(CC1)C(=O)OCC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of diethyl 1-oxo-6b,9,10,10a-tetrahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-3,8(2H,7H)-dicarboxylate (360 mg, 0.97 mmol) in DMF (20 mL) at 0° C. was added NaH (193 mg, 4.8 mmol), MeI (0.3 mL, 4.8 mmol) and stirred at rt for 16 hours. The solution was diluted with water (20 mL), and extracted ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | HI | O.CN(C)C=O | null | 16 | CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(=O)CN3C(=O)OCC.CI>O.CN(C)C=O>CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(=O)C(C)N3C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0d644445c2c049578ec7a710b1f2c5a7 | CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(=O)C(C)N3C(=O)OCC>>CCOC(=O)N1CCC2C(C1)c1cccc3c1N2CC(C)N3C(=O)OCC | CC1N(C=2C=CC=C3C2N(C1=O)C1C3CN(CC1)C(=O)OCC)C(=O)OCC.Cl>>CC1N(C=2C=CC=C3C2N(C1)C1C3CN(CC1)C(=O)OCC)C(=O)OCC | O=[C:19]1[N:18]2[CH:9]3[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:11][CH:10]3[c:12]3[cH:13][cH:14][cH:15][c:16]([c:17]32)[N:22]([C:23](=[O:24])[O:25][CH2:26][CH3:27])[CH:20]1[CH3:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]2[CH:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:15][c:16]3[c:17]1[N... | CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(=O)C(C)N3C(=O)OCC | CCOC(=O)N1CCC2C(C1)c1cccc3c1N2CC(C)N3C(=O)OCC | null | null | O.C1CCOC1 | Reduction | Reduction of tertiary amides to amines | f4b8adbbe1e8fda9e37d7419b5527bf584a957a3d24228e3b56a3b55bc1052ba | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | c1cc2c3c(c1)C1CNCCC1N3CCN2 | O=[C;H0;D3;+0:1]1-[#7:2](-[C:3])-[c:4]:[c:5]-[#7:6](-[C:7](-[#8:8])=[O;D1;H0:9])-[C:10]-1-[C;D1;H3:11]>>[#8:8]-[C:7](=[O;D1;H0:9])-[#7:6]1-[c:5]:[c:4]-[#7:2](-[C:3])-[CH2;D2;+0:1]-[C:10]-1-[C;D1;H3:11] | 69.6 | [{"value": 69.0, "product": "CC1N(C=2C=CC=C3C2N(C1)C1C3CN(CC1)C(=O)OCC)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.6, "product": "CC1N(C=2C=CC=C3C2N(C1)C1C3CN(CC1)C(=O)OCC)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | To a solution of diethyl 2-methyl-1-oxo-6b,9,10,10a-tetrahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-3,8(2H,7H)-dicarboxylate (300 mg, 0.77 mmol) in THF (10 mL) at rt was added BH3THF complex (3.8 mL, 3.8 mmol) and refluxed for 5 hours. At rt 6N HCl (10 mL) was added and stirred for 0.5 hour before the solut... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | Other | O.C1CCOC1 | null | 0.5 | CCOC(=O)N1CCC2C(C1)c1cccc3c1N2C(=O)C(C)N3C(=O)OCC>O.C1CCOC1>CCOC(=O)N1CCC2C(C1)c1cccc3c1N2CC(C)N3C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5f7d81cfb0094974a5fcbeb091b6b912 | CCOC(=O)N1CCC2C(C1)c1cccc3c1N2CC(C)N3C(=O)OCC.O=C1CCC(=O)N1Br>>CCOC(=O)N1CCC2C(C1)c1cc(Br)cc3c1N2CC(C)N3C(=O)OCC | CC1N(C=2C=CC=C3C2N(C1)C1C3CN(CC1)C(=O)OCC)C(=O)OCC.C1CC(=O)N(C1=O)Br>>BrC=1C=C2C=3N(CC(N(C3C1)C(=O)OCC)C)C1C2CN(CC1)C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]2[CH:10]([CH2:11]1)[c:12]1[cH:13][cH:14][cH:16][c:17]3[c:18]1[N:19]2[CH2:20][CH:21]([CH3:22])[N:23]3[C:24](=[O:25])[O:26][CH2:27][CH3:28].O=C1CCC(=O)N1[Br:15]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]2[CH:10]([CH2:11]1)[c:12]1[cH:13][c:14]([Br:... | CCOC(=O)N1CCC2C(C1)c1cccc3c1N2CC(C)N3C(=O)OCC.O=C1CCC(=O)N1Br | CCOC(=O)N1CCC2C(C1)c1cc(Br)cc3c1N2CC(C)N3C(=O)OCC | null | null | O.CN(C)C=O | Functional Group Interconversion | Bromination | d2c26aee9f9ca727bf352a2d7b56fa077e1ffc4c2dc8ec5b01124d6118571879 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1cc2c3c(c1)C1CNCCC1N3CCN2 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7:2]-[c:3]:[c:4]:[cH;D2;+0:5]:[c:6]:[c:7]>>[#7:2]-[c:3]:[c:4]:[c;H0;D3;+0:5](-[Br;H0;D1;+0:1]):[c:6]:[c:7] | 88.4 | [{"value": 88.0, "product": "BrC=1C=C2C=3N(CC(N(C3C1)C(=O)OCC)C)C1C2CN(CC1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.4, "product": "BrC=1C=C2C=3N(CC(N(C3C1)C(=O)OCC)C)C1C2CN(CC1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | To a solution of diethyl 2-methyl-6b,9,10,10a-tetrahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-3,8(2H,7H)-dicarboxylate (40 mg, 0.1 mmol) in DMF (10 mL) at 0° C. was added NBS (20 mg, 0.11 mmol) and stirred at 0° C. for 2 hours. The solution was diluted with water (10 mL), and extracted with EtOAc (2×20 mL).... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2.C1CCNC1 | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | HO- | O.CN(C)C=O | 0 | 2 | CCOC(=O)N1CCC2C(C1)c1cccc3c1N2CC(C)N3C(=O)OCC.O=C1CCC(=O)N1Br>O.CN(C)C=O>CCOC(=O)N1CCC2C(C1)c1cc(Br)cc3c1N2CC(C)N3C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c991ff4f0ffe4caf906b891778ebccf7 | CCOC(=O)N1CCC2C(C1)c1cc(Br)cc3c1N2CC(C)N3C(=O)OCC.OB(O)c1ccc(Cl)cc1Cl>>CCOC(=O)N1CCC2C(C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CC(C)N3C(=O)OCC | BrC=1C=C2C=3N(CC(N(C3C1)C(=O)OCC)C)C1C2CN(CC1)C(=O)OCC.ClC1=C(C=CC(=C1)Cl)B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>>ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CC(N(C3C1)C(=O)OCC)C)C1C2CN(CC1)C(=O)OCC | Br[c:14]1[cH:13][c:12]2[c:25]3[c:24]([cH:23]1)[N:30]([C:31](=[O:32])[O:33][CH2:34][CH3:35])[CH:28]([CH3:29])[CH2:27][N:26]3[CH:9]1[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:11][CH:10]12.OB(O)[c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]1[Cl:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH... | CCOC(=O)N1CCC2C(C1)c1cc(Br)cc3c1N2CC(C)N3C(=O)OCC.OB(O)c1ccc(Cl)cc1Cl | CCOC(=O)N1CCC2C(C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CC(C)N3C(=O)OCC | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | CN(C)C=O.C(C)(=O)OCC | C-C Coupling | Suzuki coupling with boronic acids | 76aadca826c052e8dd2b039b6a96f64b12ed2617c87c7ce270bedff0e0cd0dce | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cc3c4c(c2)C2CNCCC2N4CCN3)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]-[#7:6].O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[Cl;D1;H0:11]):[c:12]>>[#7:6]-[c:5]:[c:4]:[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](-[Cl;D1;H0:11]):[c:12]):[c:2]:[c:3] | 29 | [{"value": 29.0, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CC(N(C3C1)C(=O)OCC)C)C1C2CN(CC1)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.3, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CC(N(C3C1)C(=O)OCC)C)C1C2CN(CC1)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 16 | HOUR | To a solution of diethyl 5-bromo-2-methyl-6b,9,10,10a-tetrahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-3,8(2H,7H)-dicarboxylate (100 mg, 0.22 mmol) in DMF (10 mL) was added 2,4-dichlorophenyl boronic acid (63 mg, 0.33 mmol) and Na2CO3 (58 mg, 0.55 mmo, in 0.4 mL of H2O). The mixture was degassed with a strea... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2.c1ccccc1 | c1ccccc1.c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | c1ccccc1.c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C)C=O.C(C)(=O)OCC | 100 | 16 | CCOC(=O)N1CCC2C(C1)c1cc(Br)cc3c1N2CC(C)N3C(=O)OCC.OB(O)c1ccc(Cl)cc1Cl>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.CN(C)C=O.C(C)(=O)OCC>CCOC(=O)N1CCC2C(C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CC(C)N3C(=O... |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-45ef0f63e0104c3c9bf0c39e4e78f987 | CCOC(=O)N1CCC2C(C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CC(C)N3C(=O)OCC>>CC1CN2c3c(cc(-c4ccc(Cl)cc4Cl)cc3C3CNCCC32)N1 | ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CC(N(C3C1)C(=O)OCC)C)C1C2CN(CC1)C(=O)OCC.[OH-].[K+]>>ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CC(NC3C1)C)C1C2CNCC1 | CCOC(=O)[N:21]1[CH2:20][CH:19]2[c:18]3[c:5]4[c:6]([cH:7][c:8](-[c:9]5[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]5[Cl:16])[cH:17]3)[N:25](C(=O)OCC)[CH:2]([CH3:1])[CH2:3][N:4]4[CH:24]2[CH2:23][CH2:22]1>>[CH3:1][CH:2]1[CH2:3][N:4]2[c:5]3[c:6]([cH:7][c:8](-[c:9]4[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]4[Cl:16])[cH:17][c:1... | CCOC(=O)N1CCC2C(C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CC(C)N3C(=O)OCC | CC1CN2c3c(cc(-c4ccc(Cl)cc4Cl)cc3C3CNCCC32)N1 | null | null | CCCCO.C(C)(=O)OCC | Reduction | OtherReaction | 104ec19fce083dc1b862e57e6722f6d681cd1e46542715fa1d289f1df1fa3f44 | 4d54a9a4b5d62ab51cee46634e0429ca8b96a7950e75c860eb5742c8bca2fbcf | c1ccc(-c2cc3c4c(c2)C2CNCCC2N4CCN3)cc1 | C-C-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].C-C-O-C(=O)-[N;H0;D3;+0:6]1-[C:7](-[C;D1;H3:8])-[C:9]-[#7:10]-[c:11]:[c:12]-1:[c:13]>>[C;D1;H3:8]-[C:7]1-[C:9]-[#7:10]-[c:11]:[c:12](:[c:13])-[NH;D2;+0:6]-1.[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 45 | [{"value": 45.0, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CC(NC3C1)C)C1C2CNCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.5, "product": "ClC1=C(C=CC(=C1)Cl)C=1C=C2C=3N(CC(NC3C1)C)C1C2CNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 16 | HOUR | To a solution of diethyl 5-(2,4-dichlorophenyl)-2-methyl-6b,9,10,10a-tetrahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-3,8(2H,7H)-dicarboxylate (30 mg, 0.06 mmol) in 10 mL of n-BuOH was added KOH (33 mg, 0.6 mmol) and stirred at 120° C. for 16 h. The reaction was allowed to cool to ambient temperature and was... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether | Secondary amine.Secondary amine | c1cc2c3c(c1)C1C[NH]CCC1N3CC[NH]2 | c1cc2c3c(c1)C1CNCCC1N3CCN2 | c1ccccc1.c1cc2c3c(c1)C1CNCCC1N3CCN2 | HO- | CCCCO.C(C)(=O)OCC | 120 | 16 | CCOC(=O)N1CCC2C(C1)c1cc(-c3ccc(Cl)cc3Cl)cc3c1N2CC(C)N3C(=O)OCC>CCCCO.C(C)(=O)OCC>CC1CN2c3c(cc(-c4ccc(Cl)cc4Cl)cc3C3CNCCC32)N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ee37b3bbe8884342a72654bff4d2cc0e | Fc1ccccc1[CH2][Zn+].O=C(Cl)C1CCCCC1>>O=C(Cc1ccccc1F)C1CCCCC1 | [Cl-].FC1=C(C[Zn+])C=CC=C1.C1(CCCCC1)C(=O)Cl>>FC1=C(CC(=O)C2CCCCC2)C=CC=C1 | [Zn+][CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[F:10].Cl[C:2](=[O:1])[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[F:10])[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1 | Fc1ccccc1[CH2][Zn+].O=C(Cl)C1CCCCC1 | O=C(Cc1ccccc1F)C1CCCCC1 | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | null | C-C Coupling | OtherReaction | e0a45010daec094b0d5e8e4fbe0fbbb99cf9610754539ead723b25846a3ea8fc | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(Cc1ccccc1)C1CCCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[Zn+]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:5] | null | [] | 0 | CELSIUS | null | null | To a mixture of 36 ml of 2-fluorobenzylzinc chloride (0.5 M sol. in tetrahydrofuran) and 0.008 g of dichlorobis(triphenylphosphine)palladium(II) stirred at 0° C. was added dropwise via a syringe 2.14 ml of cyclohexanecarbonyl chloride. Afterwards, the reaction mixture was stirred at r.t. for 4 h, quenched with an aqueo... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | null | null | c1ccccc1.C1CCCCC1 | Zn | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | 0 | null | Fc1ccccc1[CH2][Zn+].O=C(Cl)C1CCCCC1>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl>O=C(Cc1ccccc1F)C1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-77ac6db584834c1f8375001625f5f875 | O=C(Cl)C1CCCCC1.[Zn+][CH2]c1ccccc1>>O=C(Cc1ccccc1)C1CCCCC1 | C1(CCCCC1)C(=O)Cl.[Br-].C(C1=CC=CC=C1)[Zn+]>>C1(CCCCC1)C(=O)CC1=CC=CC=C1 | Cl[C:2](=[O:1])[CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1.[Zn+][CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1>>[O:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)[CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1 | O=C(Cl)C1CCCCC1.[Zn+][CH2]c1ccccc1 | O=C(Cc1ccccc1)C1CCCCC1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | e0a45010daec094b0d5e8e4fbe0fbbb99cf9610754539ead723b25846a3ea8fc | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(Cc1ccccc1)C1CCCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[Zn+]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9])-[C:5] | 52 | [{"value": 52.0, "product": "C1(CCCCC1)C(=O)CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution of 11 ml of 0.5 M solution of benzyl zinc bromide in anhydrous tetrahydrofuran were added at 0° C. 5 mg of bis-triphenylphospinepalladium dichloride and 0.66 ml of cyclohexanecarbonyl chloride. The mixture was stirred at r.t. for 1.5 h, quenched with a saturated solution of ammonium chloride and extracted... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | null | null | c1ccccc1.C1CCCCC1 | Zn | O1CCCC1 | null | 1.5 | O=C(Cl)C1CCCCC1.[Zn+][CH2]c1ccccc1>O1CCCC1>O=C(Cc1ccccc1)C1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0f065b34f4cd4e0a9ab3bbb53d94a9e4 | CCOC(CC(C(=O)C1CCCCC1)c1ccccc1)OCC>>O=CCC(C(=O)C1CCCCC1)c1ccccc1 | C(C)OC(CC(C(=O)C1CCCCC1)C1=CC=CC=C1)OCC>>C1(CCCCC1)C(C(CC=O)C1=CC=CC=C1)=O | CCO[CH:2]([O:1]CC)[CH2:3][CH:4]([C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[O:1]=[CH:2][CH2:3][CH:4]([C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | CCOC(CC(C(=O)C1CCCCC1)c1ccccc1)OCC | O=CCC(C(=O)C1CCCCC1)c1ccccc1 | null | null | Cl.CC(=O)C | Miscellaneous | Acetal hydrolysis to aldehyde | 2c5baf4818f438d514702dbb9f9a64f069b67040aebce8bef29fab8232955599 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | O=C(Cc1ccccc1)C1CCCCC1 | C-C-O-[CH;D3;+0:1](-[C:2]-[C:3]-[C:4]=[O;D1;H0:5])-[O;H0;D2;+0:6]-C-C>>[O;D1;H0:5]=[C:4]-[C:3]-[C:2]-[CH;D2;+0:1]=[O;H0;D1;+0:6] | 100 | [{"value": 100.0, "product": "C1(CCCCC1)C(C(CC=O)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.6, "product": "C1(CCCCC1)C(C(CC=O)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 1.17 g of Compound 5b in 10 ml of acetone and 22.1 ml of 2N HCl was stirred at r.t. for 5 h. After overnight resting, the aqueous layer was extracted with EtOAc. The collected organic layers were washed with water, dried (Na2SO4) and the solvent was evaporated under vacuum to give 0.84 g (100%) of the tit... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | null | null | C1CCCCC1.c1ccccc1 | HO- | Cl.CC(=O)C | null | 8 | CCOC(CC(C(=O)C1CCCCC1)c1ccccc1)OCC>Cl.CC(=O)C>O=CCC(C(=O)C1CCCCC1)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6dd37b3ea8d64736b1e8a46281be986b | COc1ccccc1N1CCNCC1.O=CCC(C(=O)C1CCCCC1)c1ccccc1>>COc1ccccc1N1CCN(CCC(C(=O)C2CCCCC2)c2ccccc2)CC1 | C1(CCCCC1)C(C(CC=O)C1=CC=CC=C1)=O.COC1=C(C=CC=C1)N1CCNCC1.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].C(C)(=O)O>>C1(CCCCC1)C(C(CCN1CCN(CC1)C1=C(C=CC=C1)OC)C1=CC=CC=C1)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][NH:12][CH2:30][CH2:31]1.O=[CH:13][CH2:14][CH:15]([C:16](=[O:17])[CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([CH2:13][CH2:... | COc1ccccc1N1CCNCC1.O=CCC(C(=O)C1CCCCC1)c1ccccc1 | COc1ccccc1N1CCN(CCC(C(=O)C2CCCCC2)c2ccccc2)CC1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | reductive amination | 66e6667395903ee1c54d8aecc784ece1bccbdcbc9661ebcae0e6a980f9380640 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C(C1CCCCC1)C(CCN1CCN(c2ccccc2)CC1)c1ccccc1 | O=[CH;D2;+0:1]-[C:2]-[C:3]-[C:4]=[O;D1;H0:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:5]=[C:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1 | 100.3 | [{"value": 99.0, "product": "C1(CCCCC1)C(C(CCN1CCN(CC1)C1=C(C=CC=C1)OC)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.3, "product": "C1(CCCCC1)C(C(CCN1CCN(CC1)C1=C(C=CC=C1)OC)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a solution of 0.84 g of Compound 5c and 1.19 g of 1-(2-methoxyphenyl)-piperazine in 30 ml of dichloromethane, 1.48 g of sodium triacetoxyborohydride and 0.98 ml of acetic acid were added and the resulting mixture was stirred at r.t. for 5 h. After overnight resting, the organic layer was washed with excess of 1M NaO... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.C1CCCCC1.c1ccccc1 | Other | ClCCl | null | 5 | COc1ccccc1N1CCNCC1.O=CCC(C(=O)C1CCCCC1)c1ccccc1>ClCCl>COc1ccccc1N1CCN(CCC(C(=O)C2CCCCC2)c2ccccc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a2c6d18735294db9a4cec801c19b3d02 | COc1ccccc1N1CCN(CCC(C(=O)C2CCCCC2)c2ccccc2)CC1>>COc1ccccc1N1CCN(CCC(c2ccccc2)C(O)C2CCCCC2)CC1 | C1(CCCCC1)C(C(CCN1CCN(CC1)C1=C(C=CC=C1)OC)C1=CC=CC=C1)=O.[H-].C(C(C)C)[Al+]CC(C)C>>C1(CCCCC1)C(C(CCN1CCN(CC1)C1=C(C=CC=C1)OC)C1=CC=CC=C1)O | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([CH2:13][CH2:14][CH:15]([c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[C:22](=[O:23])[CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:30][CH2:31]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([CH2:13][CH2:1... | COc1ccccc1N1CCN(CCC(C(=O)C2CCCCC2)c2ccccc2)CC1 | COc1ccccc1N1CCN(CCC(c2ccccc2)C(O)C2CCCCC2)CC1 | null | null | ClCCl.C1(=CC=CC=C1)C | Reduction | Reduction of ketone to secondary alcohol | 02790ac194d8bf7ccb13d6247c59412024d87f77d2c906ef7804f021f57d5070 | 1bd3cd74b454139c0a0068ac0135836499926b274bff569df163210c6c944a89 | c1ccc(C(CCN2CCN(c3ccccc3)CC2)CC2CCCCC2)cc1 | [C:1]-[C:2](-[c:3])-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[C:6](-[C:7])-[C:8]>>[C:1]-[C:2](-[c:3])-[CH;D3;+0:4](-[OH;D1;+0:5])-[C:6](-[C:7])-[C:8] | 87.2 | [{"value": 80.0, "product": "C1(CCCCC1)C(C(CCN1CCN(CC1)C1=C(C=CC=C1)OC)C1=CC=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.2, "product": "C1(CCCCC1)C(C(CCN1CCN(CC1)C1=C(C=CC=C1)OC)C1=CC=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1 | HOUR | Into a solution of 1.21 g of Compound 5d in 60 ml of dichloromethane at −78° C., was dropped 11.5 ml of 1 M solution of diisobutylaluminum hydride (DIBAL-H) in toluene. The mixture was stirred at −78° C. for 1 h, quenched at 40° C. with a saturated aqueous solution of NH4Cl and extracted with chloroform. The collected ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.C1CCCCC1 | null | ClCCl.C1(=CC=CC=C1)C | -78 | 1 | COc1ccccc1N1CCN(CCC(C(=O)C2CCCCC2)c2ccccc2)CC1>ClCCl.C1(=CC=CC=C1)C>COc1ccccc1N1CCN(CCC(c2ccccc2)C(O)C2CCCCC2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fbaa14d6e4c243d89586713fa1c24c59 | O=P(Cl)(Cl)Cl.O=c1cnc2c([nH]1)CCCC2>>Clc1cnc2c(n1)CCCC2 | N1C(C=NC=2CCCCC12)=O.P(=O)(Cl)(Cl)Cl>>ClC1=NC=2CCCCC2N=C1 | O=P(Cl)(Cl)[Cl:1].O=[c:2]1[cH:3][n:4][c:5]2[c:6]([nH:7]1)[CH2:8][CH2:9][CH2:10][CH2:11]2>>[Cl:1][c:2]1[cH:3][n:4][c:5]2[c:6]([n:7]1)[CH2:8][CH2:9][CH2:10][CH2:11]2 | O=P(Cl)(Cl)Cl.O=c1cnc2c([nH]1)CCCC2 | Clc1cnc2c(n1)CCCC2 | null | null | null | Functional Group Interconversion | OtherReaction | 1282c63ec158ab45b09d1c279ad07e86c94206a6cfce12271ada1f3c04d3f379 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cnc2c(n1)CCCC2 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O=[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5](:[c:6](:[nH;D2;+0:7]:1)-[C:8])-[C:9]>>[C:9]-[c:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[n;H0;D2;+0:7]:[c:6]:1-[C:8] | 86 | [{"value": 86.0, "product": "ClC1=NC=2CCCCC2N=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5,6,7,8-tetrahydro-2(1H)-quinoxalinone in phosphoryl chloride (200 ml) was stirred and refluxed for 3 hours. The solvent was evaporated. The residue was taken up in ice and CH2Cl2. The mixture was basified with NH4OH. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated, ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cnc2c(n1)CCCC2 | c1cnc2c(n1)CCCC2 | c1cnc2c(n1)CCCC2 | HCl | null | null | null | O=P(Cl)(Cl)Cl.O=c1cnc2c([nH]1)CCCC2>>Clc1cnc2c(n1)CCCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a0f99a5dfa9a45848a8856bf58a18c6e | CC(=O)C(C)=O.CCOC(=O)c1cccc(N)c1N>>CCOC(=O)c1cccc2nc(C)c(C)nc12 | C(=O)([O-])[O-].[K+].[K+].CC(C(C)=O)=O.S(=O)(=O)([O-])S(=O)[O-].[Na+].[Na+].NC1=C(C(=O)OCC)C=CC=C1N>>CC1=NC=2C=CC=C(C2N=C1C)C(=O)OCC | O=[C:12]([CH3:13])[C:14](=O)[CH3:15].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([NH2:11])[c:17]1[NH2:16]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][c:10]2[n:11][c:12]([CH3:13])[c:14]([CH3:15])[n:16][c:17]12 | CC(=O)C(C)=O.CCOC(=O)c1cccc(N)c1N | CCOC(=O)c1cccc2nc(C)c(C)nc12 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 80ad7d4b359f2683f57c053570cf5c6857c4f32e8ec9869e4f38f79c70cafc8c | d53d864708a4cd37c2fe33ca368498c017ca81ee7d694ff92f9c935efef6bc9e | c1ccc2nccnc2c1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=O)-[C;D1;H3:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](-[NH2;D1;+0:10]):[c:11](-[NH2;D1;+0:12]):[c:13]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:3](-[C;D1;H3:4]):[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D2;+0:12]:[c:11]:1:[c:13] | 67.2 | [{"value": 67.0, "product": "CC1=NC=2C=CC=C(C2N=C1C)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.2, "product": "CC1=NC=2C=CC=C(C2N=C1C)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 12 | HOUR | 2,3-Butanedione (0.0776 mol) was added at room temperature to a solution of sodium pyrosulfite (0.1 mol) in water (75 ml). The mixture was heated to 70° C. and then added to a solution of ethyl 2,3-diaminobenzoate (0.0776 mol) in water (75 ml). The mixture was stirred at 100° C. for 12 hours, cooled, basified with K2CO... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | HO- | O | 70 | 12 | CC(=O)C(C)=O.CCOC(=O)c1cccc(N)c1N>O>CCOC(=O)c1cccc2nc(C)c(C)nc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-60ac4e1b4f544e8ba45a2727dbe686f7 | CN(C)C=O.Cc1ccc2cccc(Br)c2n1>>Cc1ccc2cccc(C=O)c2n1 | [NH4+].[Cl-].CN(C)C=O.BrC=1C=CC=C2C=CC(=NC12)C.[NH4+].[Cl-].C(CCC)[Li].CCCCCC>>CC1=NC2=C(C=CC=C2C=C1)C=O | CN(C)[CH:10]=[O:11].Br[c:9]1[cH:8][cH:7][cH:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:13][c:12]21>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([CH:10]=[O:11])[c:12]2[n:13]1 | CN(C)C=O.Cc1ccc2cccc(Br)c2n1 | Cc1ccc2cccc(C=O)c2n1 | null | null | O1CCCC1.C(C)OCC.C(C)O | C-C Coupling | Bouveault aldehyde synthesis | 6b2ee0acc9e3f7a1d11938f6d9a15d00e6e8ead5dccbbdb0a71f0ce23f9e361d | afd09ced98f25d311f21cc04ba6a50fe7e5516de47e17484683ded13d323b1b2 | c1ccc2ncccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7].C-N(-C)-[CH;D2;+0:8]=[O;D1;H0:9]>>[O;D1;H0:9]=[CH;D2;+0:8]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7] | 129.8 | [{"value": 100.0, "product": "CC1=NC2=C(C=CC=C2C=C1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 129.8, "product": "CC1=NC2=C(C=CC=C2C=C1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | 30 | MINUTE | 8-Bromo-2-methylquinoline (0.0675 mol) was added portionwise at −70° C. under N2 flow to a mixture of a solution of butyllithium in hexane (1.6M) (0.135 mol) in tetrahydrofuran (300 ml) and diethyl ether (300 ml). The mixture was stirred for 30 minutes. A solution of DMF (0.405 mol) in tetrahydrofuran (100 ml) was adde... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Aldehyde | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HBr | O1CCCC1.C(C)OCC.C(C)O | -70 | 0.5 | CN(C)C=O.Cc1ccc2cccc(Br)c2n1>O1CCCC1.C(C)OCC.C(C)O>Cc1ccc2cccc(C=O)c2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e14ca53373f947628d9a61d018702f84 | COc1cc2ccccc2nc1C>>COc1cc2c(nc1C)CCCC2 | COC=1C(=NC2=CC=CC=C2C1)C.[H][H]>>COC=1C(=NC=2CCCCC2C1)C | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([n:7][c:8]1[CH3:9])[cH:10][cH:11][cH:12][cH:13]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([n:7][c:8]1[CH3:9])[CH2:10][CH2:11][CH2:12][CH2:13]2 | COc1cc2ccccc2nc1C | COc1cc2c(nc1C)CCCC2 | null | [Pd] | FC(C(=O)O)(F)F | Reduction | OtherReaction | 9304ef4b145871f015039f0f87a526880ef1ccc35aa5ca268466778d480e3cfe | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1cnc2c(c1)CCCC2 | [c:1]:[c:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[c:7]:1:[#7;a:8]:[c:9]>>[c:1]:[c:2]1:[c:7](:[#7;a:8]:[c:9])-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[CH2;D2;+0:3]-1 | 99.6 | [{"value": 99.6, "product": "COC=1C(=NC=2CCCCC2C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 3-methoxy-2-methylquinoline (0.081 mol) in trifluoro-acetic acid (150 ml) was hydrogenated at room temperature under a 34 bar pressure for 48 hours with palladium on activated carbon (2 g) as a catalyst. After uptake of hydrogen (2 equiv.), the catalyst was filtered through celite and washed with H2O. The ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2ncccc2c1 | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | null | [Pd].FC(C(=O)O)(F)F | null | null | COc1cc2ccccc2nc1C>[Pd].FC(C(=O)O)(F)F>COc1cc2c(nc1C)CCCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ec5c825169ea4d32846c8d18ec613a69 | BrP(Br)Br.Cc1ccc2c(n1)C(O)CCC2>>Cc1ccc2c(n1)C(Br)CCC2 | P(Br)(Br)Br.CC1=NC=2C(CCCC2C=C1)O.CC1=NC=2C(CCCC2C=C1)O.[OH-].[Na+]>>BrC1CCCC=2C=CC(=NC12)C | BrP(Br)[Br:9].O[CH:8]1[c:6]2[c:5]([cH:4][cH:3][c:2]([CH3:1])[n:7]2)[CH2:12][CH2:11][CH2:10]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([n:7]1)[CH:8]([Br:9])[CH2:10][CH2:11][CH2:12]2 | BrP(Br)Br.Cc1ccc2c(n1)C(O)CCC2 | Cc1ccc2c(n1)C(Br)CCC2 | null | null | C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 4eb07b06ca6bf965c8defd9b5553b478ca022fffadf84ff14f680b94d0889668 | 495868b18ac37eabad313a8861412e57f019fb3569a2b2e50afa3ee29413ec02 | c1cnc2c(c1)CCCC2 | Br-P(-Br)-[Br;H0;D1;+0:1].O-[CH;D3;+0:2](-[C:3]-[C:4])-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[Br;H0;D1;+0:1]-[CH;D3;+0:2](-[C:3]-[C:4])-[c:5](:[c:6]):[#7;a:7]:[c:8] | 84.2 | [{"value": 29.0, "product": "BrC1CCCC=2C=CC(=NC12)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.2, "product": "BrC1CCCC=2C=CC(=NC12)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Phosphorus tribromide (0.0105 mol) was added dropwise at 0° C./5° C. under N2 flow to a mixture of (±)-5,6,7,8-tetrahydro-2-methyl-8-quinolinol (intermediate 17) (0.03 mol) in toluene (20 ml). The mixture was brought to room temperature and stirred at room temperature overnight. Ice water was added. The mixture was bas... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Secondary halide | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | HBr | C1(=CC=CC=C1)C | null | 8 | BrP(Br)Br.Cc1ccc2c(n1)C(O)CCC2>C1(=CC=CC=C1)C>Cc1ccc2c(n1)C(Br)CCC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a51d87559ef241039e7ebf5f2a91a9df | O=CNc1cccc2cccnc12.O=[N+]([O-])c1ccccc1Cl>>O=[N+]([O-])c1ccccc1Nc1cccc2cccnc12 | ClC1=C(C=CC=C1)[N+](=O)[O-].N1=CC=CC2=CC=CC(=C12)NC=O.[H-].[Na+].O>>[N+](=O)([O-])C1=C(C=CC=C1)NC=1C=CC=C2C=CC=NC12 | O=C[NH:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][n:19][c:20]12.Cl[c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][cH:8]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[NH:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][n:19][c:20]12 | O=CNc1cccc2cccnc12.O=[N+]([O-])c1ccccc1Cl | O=[N+]([O-])c1ccccc1Nc1cccc2cccnc12 | null | null | CN(C)C=O | Functional Group Addition | OtherReaction | 1821c4c8060175bf390d94295fd88f196f59741d36e2f9631c86d4ef54fe9389 | 1d196ba5d3235d0f70196a5df15f7e51895b680a6c5e6ae9c7e22f63a0e77a26 | c1ccc(Nc2cccc3cccnc23)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6].O=C-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10](:[c:11]):[#7;a:12]:[c:13]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10](:[c:11]):[#7;a:12]:[c:13]):[c:2]:[c:3] | 21.2 | [{"value": 21.0, "product": "[N+](=O)([O-])C1=C(C=CC=C1)NC=1C=CC=C2C=CC=NC12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.2, "product": "[N+](=O)([O-])C1=C(C=CC=C1)NC=1C=CC=C2C=CC=NC12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A dispersion of sodium hydride in mineral oil (0.261 mol) was added portionwise at room temperature under N2 flow to a mixture of N-8-quinolinylformamide (0.174 mol) in DMF (500 ml). The mixture was stirred at room temperature for 1 hour. A solution of 1-chloro-2-nitrobenzene (0.53 mol) in DMF (200 ml) was added dropwi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amide | Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccc2ncccc2c1 | HCl | CN(C)C=O | null | 1 | O=CNc1cccc2cccnc12.O=[N+]([O-])c1ccccc1Cl>CN(C)C=O>O=[N+]([O-])c1ccccc1Nc1cccc2cccnc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9ca8affbf2c845d8a5ea54ffd2219358 | CCOC(OCC)OCC.O=Cc1cccc2cccnc12>>CCOC(OCC)c1cccc2cccnc12 | C(=O)([O-])[O-].[K+].[K+].N1=CC=CC2=CC=CC(=C12)C=O.C(C)OC(OCC)OCC.CC1=CC=C(C=C1)S(=O)(=O)O>>C(C)OC(C=1C=CC=C2C=CC=NC12)OCC | CCOC(O[CH2:2][CH3:1])[O:5][CH2:6][CH3:7].[O:3]=[CH:4][c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][n:16][c:17]12>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][n:16][c:17]12 | CCOC(OCC)OCC.O=Cc1cccc2cccnc12 | CCOC(OCC)c1cccc2cccnc12 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | fcd88c7abf874cee525e2d08e112aab4759e77ad93b33f36b8306c7913ea31c2 | 11306b4f2dea9cefbc3d550c8afb389271a44b7cc69c06172e6b191dd38b2284 | c1ccc2ncccc2c1 | C-C-O-C(-O-[CH2;D2;+0:1]-[C;D1;H3:2])-[O;H0;D2;+0:3]-[C:4]-[C;D1;H3:5].[O;H0;D1;+0:6]=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10](:[c:11]):[#7;a:12]:[c:13]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[CH;D3;+0:7](-[O;H0;D2;+0:3]-[C:4]-[C;D1;H3:5])-[c:8](:[c:9]):[c:10](:[c:11]):[#7;a:12]:[c:13] | 84.6 | [{"value": 80.0, "product": "C(C)OC(C=1C=CC=C2C=CC=NC12)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.6, "product": "C(C)OC(C=1C=CC=C2C=CC=NC12)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 8-quinolinecarboxaldehyde (0.248 mol), triethoxymethane (0.4464 mol) and 4-methylbenzenesulfonic acid (4 g) in ethanol (250 ml) was stirred and refluxed for 1 hour, brought to room temperature, poured out into K2CO3 10% and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered and ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether.Ether.Ether | Ether.Ether | null | null | c1ccc2ncccc2c1 | HO- | C(C)O | null | null | CCOC(OCC)OCC.O=Cc1cccc2cccnc12>C(C)O>CCOC(OCC)c1cccc2cccnc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3d5a2eebd5444a19a9d7ea089a49bc03 | CCO.Cc1ccc(S(=O)(=O)O)cc1.O=Cc1ccc2ccccc2n1>>CCOC(OCC)c1ccc2ccccc2n1 | N1=C(C=CC2=CC=CC=C12)C=O.CC1=CC=C(C=C1)S(=O)(=O)O.C(C)O>>C(C)OC(C1=NC2=CC=CC=C2C=C1)OCC | [OH:5][CH2:6][CH3:7].Cc1ccc(S(=O)(=O)O)[cH:1][cH:2]1.[O:3]=[CH:4][c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[n:17]1>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[c:8]1[cH:9][cH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[n:17]1 | CCO.Cc1ccc(S(=O)(=O)O)cc1.O=Cc1ccc2ccccc2n1 | CCOC(OCC)c1ccc2ccccc2n1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | a41db0c1ee2b64dae978f85650c33aa8b5de4efe5372b010d3f57b5638a2f80a | 0d641fbcfd93c2628ed6fe4905bfe9d21a8c042d9bd5e63f31d12bc8ee448be4 | c1ccc2ncccc2c1 | C-c1:[cH;D2;+0:1]:[cH;D2;+0:2]:c(-S(-O)(=O)=O):c:c:1.[C;D1;H3:3]-[C:4]-[OH;D1;+0:5].[O;H0;D1;+0:6]=[CH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[C;D1;H3:3]-[C:4]-[O;H0;D2;+0:5]-[CH;D3;+0:7](-[O;H0;D2;+0:6]-[CH2;D2;+0:1]-[CH3;D1;+0:2])-[c:8](:[c:9]):[#7;a:10]:[c:11] | null | [] | null | null | null | null | A mixture of 2-quinolinecarboxaldehyde (0.08 mol) and 4-methylbenzenesulfonic acid (0.25 g) in ethanol (100 ml) was stirred and refluxed for 48 hours and brought to room temperature. The reaction was carried out again using the same quantities. The mixtures were combined. The solvent was evaporated. The residue was tak... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aldehyde.Primary alcohol | Ether.Ether | c1ccccc1 | null | c1ccc2ncccc2c1 | TsOH.HO- | null | null | null | CCO.Cc1ccc(S(=O)(=O)O)cc1.O=Cc1ccc2ccccc2n1>>CCOC(OCC)c1ccc2ccccc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d01099ba7a7745ea9ec56d0be6ad390a | CC(C)C(CO)N(C(=O)O)C(C)(C)C.Cc1ccc(S(=O)(=O)Cl)cc1>>Cc1ccc(S(=O)(=O)OCC(NC(=O)OC(C)(C)C)C(C)C)cc1 | CC1=CC=C(C=C1)S(=O)(=O)Cl.CC(C)(C)N(C(O)=O)C(C(C)C)CO.O>>CC1=CC=C(C=C1)S(=O)(=O)OCC(C(C)C)NC(OC(C)(C)C)=O | [OH:9][CH2:10][CH:11]([N:12]([C:13](=[O:14])[OH:15])[C:16]([CH3:17])([CH3:18])[CH3:19])[CH:20]([CH3:21])[CH3:22].Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:24][cH:23]1)(=[O:7])=[O:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19]... | CC(C)C(CO)N(C(=O)O)C(C)(C)C.Cc1ccc(S(=O)(=O)Cl)cc1 | Cc1ccc(S(=O)(=O)OCC(NC(=O)OC(C)(C)C)C(C)C)cc1 | null | null | N1=CC=CC=C1 | Protection | OtherReaction | db06ccc74404c99bedd0938c8e49fa1847f8469ffa2dc5725a343c45e4efbc6e | 719bbcc3bcf5c95f3deccecbe2f76966ae2f47c5ebad05f7b7b9b81f1532a3c7 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8](-[C:9]-[OH;D1;+0:10])-[N;H0;D3;+0:11](-[C:12](=[O;D1;H0:13])-[OH;D1;+0:14])-[C;H0;D4;+0:15](-[C;D1;H3:16])(-[C;D1;H3:17])-[C;D1;H3:18]>>[C:7]-[C:8](-[C:9]-[O;H0;D2;+0:10]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6])-[NH;D2;... | 123.4 | [{"value": 68.0, "product": "CC1=CC=C(C=C1)S(=O)(=O)OCC(C(C)C)NC(OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 123.4, "product": "CC1=CC=C(C=C1)S(=O)(=O)OCC(C(C)C)NC(OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 10 | CELSIUS | 2 | HOUR | 4-Methylbenzenesulfonyl chloride (0.2222 mol) was added portionwise at 10° C. to a mixture of 1,1-dimethylethyl [1-(hydroxymethyl)-2-methylpropyl]carbamic acid (ester) (0.202 mol) in pyridine (65 ml). The mixture was stirred at 10° C. for 2 hours. H2O (75 ml) was added at 10° C. The precipitate was filtered off, washed... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Carbamic acid.Primary alcohol.Sulfonyl halide | Tosylate.Carbamic ester.Ether.Boc | null | null | c1ccccc1 | HCl | N1=CC=CC=C1 | 10 | 2 | CC(C)C(CO)N(C(=O)O)C(C)(C)C.Cc1ccc(S(=O)(=O)Cl)cc1>N1=CC=CC=C1>Cc1ccc(S(=O)(=O)OCC(NC(=O)OC(C)(C)C)C(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f06646f0255f405a83ee2f07535442db | CC(C)C(=O)CN1CCC(Nc2nc3ccccc3[nH]2)CC1>>CC(C)C(N)CN1CCC(Nc2nc3ccccc3[nH]2)CC1 | N1C(=NC2=C1C=CC=C2)NC2CCN(CC2)CC(C(C)C)=O.C1(=CC=CC=C1)CN>>NC(CN1CCC(CC1)NC1=NC2=C(N1)C=CC=C2)C(C)C | O=[C:4]([CH:2]([CH3:1])[CH3:3])[CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([NH:11][c:12]2[n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[nH:20]2)[CH2:21][CH2:22]1>>[CH3:1][CH:2]([CH3:3])[CH:4]([NH2:5])[CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([NH:11][c:12]2[n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[nH:20]2)[CH2:21][CH2:22]1 | CC(C)C(=O)CN1CCC(Nc2nc3ccccc3[nH]2)CC1 | CC(C)C(N)CN1CCC(Nc2nc3ccccc3[nH]2)CC1 | null | [Pd] | CO | Functional Group Interconversion | Mignonac reaction | 14af499c4b742b1ab2135a986a4f7f4e6dda0ad50987736be8cf00d531c63192 | 2ef9e3e9915394571ec6196ff6ea06bca9f3dff8c6f6f43c81edc876014a94a5 | c1ccc2[nH]c(NC3CCNCC3)nc2c1 | O=[C;H0;D3;+0:1](-[C:2]-[#7:3])-[C:4](-[C;D1;H3:5])-[C;D1;H3:6]>>[#7:3]-[C:2]-[CH;D3;+0:1](-[N;D1;H2:7])-[C:4](-[C;D1;H3:5])-[C;D1;H3:6] | 4.4 | [{"value": 4.4, "product": "NC(CN1CCC(CC1)NC1=NC2=C(N1)C=CC=C2)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A mixture of 1-[4-(1H-benzimidazol-2-ylamino)-1-piperidinyl]-3-methyl-2-butanone (0.03 mol) and benzenemethanamine (0.09 mol) in methanol (200 ml) was hydrogenated at 40° C. under a 3 bar pressure for 48 hours with palladium on activated carbon (1.3 g) as a catalyst. After uptake of hydrogen, the catalyst was filtered ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary amine | null | null | C1CC[NH]CC1.c1ccc2[nH]cnc2c1 | null | [Pd].CO | null | 24 | CC(C)C(=O)CN1CCC(Nc2nc3ccccc3[nH]2)CC1>[Pd].CO>CC(C)C(N)CN1CCC(Nc2nc3ccccc3[nH]2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1031a038c29a45a5bfb270ecacaba076 | CC(C)C(=O)CN1CCC(Nc2nc3ccccc3n2-c2cccc3cccnc23)CC1>>CC(C)C(=O)CN1CCC(Nc2nc3ccccc3n2-c2cccc3c2NCCC3)CC1 | N1=CC=CC2=CC=CC(=C12)N1C(=NC2=C1C=CC=C2)NC2CCN(CC2)CC(C(C)C)=O.C1(=CC=CC=C1)CN>>N1CCCC2=CC=CC(=C12)N1C(=NC2=C1C=CC=C2)NC2CCN(CC2)CC(C(C)C)=O | [CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([NH:11][c:12]2[n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[n:20]2-[c:21]2[cH:22][cH:23][cH:24][c:25]3[c:26]2[n:27][cH:28][cH:29][cH:30]3)[CH2:31][CH2:32]1>>[CH3:1][CH:2]([CH3:3])[C:4](=[O:5])[CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([NH:11][c:12]2[n:13]... | CC(C)C(=O)CN1CCC(Nc2nc3ccccc3n2-c2cccc3cccnc23)CC1 | CC(C)C(=O)CN1CCC(Nc2nc3ccccc3n2-c2cccc3c2NCCC3)CC1 | null | [Pd] | CO | Reduction | OtherReaction | 0f501d7f6563b973124f46b9ac99227bf4e9d23710ef3fe61283d96ce59150d0 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | c1cc2c(c(-n3c(NC4CCNCC4)nc4ccccc43)c1)NCCC2 | [c:1]:[c:2]1:[n;H0;D2;+0:3]:[cH;D2;+0:4]:[cH;D2;+0:5]:[cH;D2;+0:6]:[c:7]:1:[c:8]>>[c:1]:[c:2]1:[c:7](:[c:8])-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[NH;D2;+0:3]-1 | 27.1 | [{"value": 27.1, "product": "N1CCCC2=CC=CC(=C12)N1C(=NC2=C1C=CC=C2)NC2CCN(CC2)CC(C(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A mixture of 1-[4-[[1-(8-quinolinyl)-1H-benzimidazol-2-yl]amino]1-piperidinyl]-3-methyl-2-butanone (0.0222 mol) and benzenemethanamine (0.0666 mol) in methanol (250 ml) was hydrogenated at 40° C. under a 3 bar pressure for 24 hours with palladium on activated carbon (1.5 g) as a catalyst. After uptake of hydrogen, the ... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccc2ncccc2c1 | c1ccc2c(c1)CCCN2 | C1CC[NH]CC1.c1nc2ccccc2[nH]1.c1ccc2c(c1)CCCN2 | null | [Pd].CO | null | 24 | CC(C)C(=O)CN1CCC(Nc2nc3ccccc3n2-c2cccc3cccnc23)CC1>[Pd].CO>CC(C)C(=O)CN1CCC(Nc2nc3ccccc3n2-c2cccc3c2NCCC3)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-777e8d975bae46508dbc8e95dcfff963 | N#CCCl.c1ccc2c(Cn3c(NC4CCNCC4)nc4ccccc43)ccnc2c1>>N#CCN1CCC(Nc2nc3ccccc3n2Cc2ccnc3ccccc23)CC1 | N1CCC(CC1)NC1=NC2=C(N1CC1=CC=NC3=CC=CC=C13)C=CC=C2.ClCC#N.[I-].[K+].C([O-])([O-])=O.[K+].[K+]>>N1=CC=C(C2=CC=CC=C12)CN1C(=NC2=C1C=CC=C2)NC2CCN(CC2)CC#N | Cl[CH2:3][C:2]#[N:1].[NH:4]1[CH2:5][CH2:6][CH:7]([NH:8][c:9]2[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[n:17]2[CH2:18][c:19]2[cH:20][cH:21][n:22][c:23]3[cH:24][cH:25][cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1>>[N:1]#[C:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([NH:8][c:9]2[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[... | N#CCCl.c1ccc2c(Cn3c(NC4CCNCC4)nc4ccccc43)ccnc2c1 | N#CCN1CCC(Nc2nc3ccccc3n2Cc2ccnc3ccccc23)CC1 | null | null | O.CC(CC(C)=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(Cn3c(NC4CCNCC4)nc4ccccc43)ccnc2c1 | Cl-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3])-[C:7]-[C:8] | 18.4 | [{"value": 18.4, "product": "N1=CC=C(C2=CC=CC=C12)CN1C(=NC2=C1C=CC=C2)NC2CCN(CC2)CC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of N-(4-piperidinyl)-1-(4-quinolinylmethyl)-1H-benzimidazol-2-amine (comp. 23) (0.0129 mol), chloroacetonitrile (0.0155 mol), potassium iodide (0.00129 mol) and potassium carbonate (0.0258 mol) in 4-methyl-2-pentanone (80 ml) was stirred and refluxed for 5 hours. H2O was added. The solvent was evaporated. H2O... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1nc2ccccc2[nH]1.c1ccc2ncccc2c1 | HCl | O.CC(CC(C)=O)C | null | null | N#CCCl.c1ccc2c(Cn3c(NC4CCNCC4)nc4ccccc43)ccnc2c1>O.CC(CC(C)=O)C>N#CCN1CCC(Nc2nc3ccccc3n2Cc2ccnc3ccccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0087de8c0dd14e0d8ed5fc816b51a058 | CC#N.CCOC(c1nc2ccccc2cc1OC)n1c(NC2CCNCC2)nc2ccccc21.O=C([O-])[O-]>>CCOC(c1nc2ccccc2cc1OC)n1c(NC2CCN(CC(NC(=O)OC(C)(C)C)C(C)C)CC2)nc2ccccc21 | C(C)OC(N1C(=NC2=C1C=CC=C2)NC2CCNCC2)C2=NC1=CC=CC=C1C=C2OC.C([O-])([O-])=O.[K+].[K+].C(C)#N>>C(C)OC(N1C(=NC2=C1C=CC=C2)NC2CCN(CC2)CC(C(C)C)NC(OC(C)(C)C)=O)C2=NC1=CC=CC=C1C=C2OC | [CH3:24][C:25]#[N:26].[CH3:1][CH2:2][O:3][CH:4]([c:5]1[n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[cH:13][c:14]1[O:15][CH3:16])[n:17]1[c:18]([NH:19][CH:20]2[CH2:21][CH2:22][NH:23][CH2:37][CH2:38]2)[n:39][c:40]2[cH:41][cH:42][cH:43][cH:44][c:45]12.[O-][C:27](=[O:28])[O-:29]>>[CH3:1][CH2:2][O:3][CH:4]([c:5]1[n:6][c:7]2[c... | CC#N.CCOC(c1nc2ccccc2cc1OC)n1c(NC2CCNCC2)nc2ccccc21.O=C([O-])[O-] | CCOC(c1nc2ccccc2cc1OC)n1c(NC2CCN(CC(NC(=O)OC(C)(C)C)C(C)C)CC2)nc2ccccc21 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 86b124de698592091f05727e0d9cafd3b33acc7cb0420d7cca188b435c895043 | 937da2521b5452a60917b079f45a86f63903cfd1df228982b69ca749b25f83f7 | c1ccc2nc(Cn3c(NC4CCNCC4)nc4ccccc43)ccc2c1 | [CH3;D1;+0:1]-[C;H0;D2;+0:2]#[N;H0;D1;+0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8].[O-;H0;D1:9]-[C;H0;D3;+0:10](-[O-])=[O;D1;H0:11]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[CH;D3;+0:2](-[NH;D2;+0:3]-[C;H0;D3;+0:10](=[O;D1;H0:11])-[O;H0;D2;+0:9]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15])-[C:16](-[C;D1;H3:17])-[... | 23 | [{"value": 23.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 1 | HOUR | Intermediate (32) (0.1382 mol) was added at 55° C. to a mixture of (±)-1-[ethoxy(3-methoxy-2-quinolinyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-amine (0.0346 mol) and potassium carbonate (0.242 mol) in acetonitrile (108 ml) and DMF (20 ml) (1 equiv of intermediate (32) was added every hour). The mixture was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Secondary amine | Carbamic ester.Ether.Tertiary amine.Boc | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2ncccc2c1.C1CC[NH]CC1.c1nc2ccccc2[nH]1 | null | CN(C)C=O | 55 | 1 | CC#N.CCOC(c1nc2ccccc2cc1OC)n1c(NC2CCNCC2)nc2ccccc21.O=C([O-])[O-]>CN(C)C=O>CCOC(c1nc2ccccc2cc1OC)n1c(NC2CCN(CC(NC(=O)OC(C)(C)C)C(C)C)CC2)nc2ccccc21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5cbaa8d5463e48db9ab3b9ad615b1d9a | COc1cc2c(nc1Cn1c(NC3CCN(CC(N)C(C)C)CC3)nc3ccccc31)CCCC2.Cl.Cl>>CC(C)C(N)CN1CCC(Nc2nc3ccccc3n2Cc2nc3c(cc2O)CCCC3)CC1.Cl.Cl | [NH4+].[OH-].O.Cl.Cl.Cl.Cl.NC(CN1CCC(CC1)NC1=NC2=C(N1CC1=NC=3CCCCC3C=C1OC)C=CC=C2)C(C)C.C(=O)([O-])[O-].[K+].[K+].BrB(Br)Br>>O.Cl.Cl.Cl.Cl.NC(CN1CCC(CC1)NC1=NC2=C(N1CC1=NC=3CCCCC3C=C1O)C=CC=C2)C(C)C | C[O:28][c:27]1[c:22]([CH2:21][n:20]2[c:12]([NH:11][CH:10]3[CH2:9][CH2:8][N:7]([CH2:6][CH:4]([CH:2]([CH3:1])[CH3:3])[NH2:5])[CH2:34][CH2:33]3)[n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]32)[n:23][c:24]2[c:25]([cH:26]1)[CH2:32][CH2:31][CH2:30][CH2:29]2.[ClH:36].[ClH:38]>>[CH3:1][CH:2]([CH3:3])[CH:4]([NH2:5])[CH2:6][N:... | COc1cc2c(nc1Cn1c(NC3CCN(CC(N)C(C)C)CC3)nc3ccccc31)CCCC2.Cl.Cl | CC(C)C(N)CN1CCC(Nc2nc3ccccc3n2Cc2nc3c(cc2O)CCCC3)CC1.Cl.Cl | null | null | ClCCl | C-C Coupling | OtherReaction | 5041c0a04bc37f2e4389098854967a21b078c8276fd88e518dbe1383c1b59387 | 7e7da33d0069dcc5669156a71f2ea38e16dcea58a7086356ac070b4210cbe68b | c1ccc2c(c1)nc(NC1CCNCC1)n2Cc1ccc2c(n1)CCCC2 | C-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c;H0;D3;+0:4]2:[c;H0;D3;+0:5](:[#7;a:6]:[c:7]:1-[C:8])-[CH2;D2;+0:9]-[C:10]-[C:11]-[CH2;D2;+0:12]-2>>[C:8]-[c:7]1:[#7;a:6]:[c;H0;D3;+0:5]2:[c;H0;D3;+0:4](:[c:3]:[c:2]:1-[OH;D1;+0:1])-[CH2;D2;+0:9]-[C:10]-[C:11]-[CH2;D2;+0:12]-2 | 37 | [{"value": 37.0, "product": "O.Cl.Cl.Cl.Cl.NC(CN1CCC(CC1)NC1=NC2=C(N1CC1=NC=3CCCCC3C=C1O)C=CC=C2)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | (±)-N-[1-(2-amino-3-methylbutyl)-4-piperidinyl]-1-[(5,6,7,8-tetrahydro-3-methoxy-2-quinolinyl)methyl]-1H-benzimidazol-2-amine tetrahydrochloride monohydrate (0.0021—O— mol) was basified with K2CO3 10%. The mixture was extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and the solvent was ev... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1cnc2c(c1)CCCC2 | c1cnc2c(c1)CCCC2 | C1CC[NH]CC1.c1nc2ccccc2[nH]1.c1cnc2c(c1)CCCC2 | Other | ClCCl | 0 | 8 | COc1cc2c(nc1Cn1c(NC3CCN(CC(N)C(C)C)CC3)nc3ccccc31)CCCC2.Cl.Cl>ClCCl>CC(C)C(N)CN1CCC(Nc2nc3ccccc3n2Cc2nc3c(cc2O)CCCC3)CC1.Cl.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bb490914043a4089a4b4985a7be43596 | C1CCNCC1.O=Cc1ccc(O)cc1>>Oc1ccc(CN2CCCCC2)cc1 | C([O-])(O)=O.[Na+].OC1=CC=C(C=O)C=C1.N1CCCCC1.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>N1(CCCCC1)CC1=CC=C(C=C1)O | [NH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1.O=[CH:6][c:5]1[cH:4][cH:3][c:2]([OH:1])[cH:14][cH:13]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[cH:13][cH:14]1 | C1CCNCC1.O=Cc1ccc(O)cc1 | Oc1ccc(CN2CCCCC2)cc1 | null | null | C(C)(=O)O.ClCCCl | Heteroatom Alkylation and Arylation | reductive amination | d0e659bc8d1e29e09a61320b4c537e66ad57335a51368c8bd48de9bdffa59372 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(CN2CCCCC2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:8]-[C:9] | null | [] | null | null | 16 | HOUR | A solution of 4-hydroxybenzaldehyde (10 g), piperidine (8.9 mL), and acetic acid (4.7 mL) in DCE (200 mL) was treated with sodium triacetoxyborohydride (24 g). After 16 h, the resulting mixture was treated with saturated aqueous sodium bicarbonate (100 mL) and extracted with DCM (5×100 mL). The combined organic phases ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | Other | C(C)(=O)O.ClCCCl | null | 16 | C1CCNCC1.O=Cc1ccc(O)cc1>C(C)(=O)O.ClCCCl>Oc1ccc(CN2CCCCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-346124e808e24aa7ad3300eb46a48213 | CC(C)(C)OC(=O)N1CCC(O)CC1.CC(C)(C)OC(=O)N1CCN(c2ccc(O)cc2)CC1>>CC(C)(C)OC(=O)N1CCC(Oc2ccc(N3CCN(C(=O)OC(C)(C)C)CC3)cc2)CC1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(C)(C)OC(=O)N1CCN(CC1)C1=CC=C(C=C1)O.C(C)(C)(C)OC(=O)N1CCC(CC1)O.CC(C)(C)OC(=O)/N=N/C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)C1=CC=C(C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C | O[CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:33][CH2:32]1.[OH:12][c:13]1[cH:14][cH:15][c:16]([N:17]2[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]2)[cH:30][cH:31]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:1... | CC(C)(C)OC(=O)N1CCC(O)CC1.CC(C)(C)OC(=O)N1CCN(c2ccc(O)cc2)CC1 | CC(C)(C)OC(=O)N1CCC(Oc2ccc(N3CCN(C(=O)OC(C)(C)C)CC3)cc2)CC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | a9e936b0e9135225700edbab1c7696738b7f1f0756494b6ceeeda63b184d572f | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1cc(N2CCNCC2)ccc1OC1CCNCC1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:10] | 62 | [{"value": 15.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.0, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C1=CC=C(C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A suspension of 4-(4-Hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (3.11 g), 4-Hydroxy-piperidine-1-carboxylic acid tert-butyl ester (3.51 g), and polymer supported triphenylphosphine (6.25 g; loading: 3 mmol/g) in DCM (100 mL) was treated with di-tert-butylazodicarboxylate (3.78 g). After 24 h, the res... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.C1C[NH]CC[NH]1 | HO- | C(Cl)Cl | null | 24 | CC(C)(C)OC(=O)N1CCC(O)CC1.CC(C)(C)OC(=O)N1CCN(c2ccc(O)cc2)CC1>C(Cl)Cl>CC(C)(C)OC(=O)N1CCC(Oc2ccc(N3CCN(C(=O)OC(C)(C)C)CC3)cc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3fc973aa2db4d2bb873ff11623b4a2f | CCC[CH2][Sn]([Cl])([Cl])[CH2]CCC.c1cn(-c2ccc(OC3CCNCC3)cc2)cn1>>CC(C)CN1CCC(Oc2ccc(-n3ccnc3)cc2)CC1 | N1(C=NC=C1)C1=CC=C(OC2CCNCC2)C=C1.C1(CCCCC1)=O.C(CCC)[Sn](CCCC)(Cl)Cl.C1(=CC=CC=C1)[SiH3]>>N1(C=NC=C1)C1=CC=C(OC2CCN(CC2)CC(C)C)C=C1 | C[CH2:3][CH2:2][CH2:4][Sn]([Cl])([Cl])[CH2]CC[CH3:1].[NH:5]1[CH2:6][CH2:7][CH:8]([O:9][c:10]2[cH:11][cH:12][c:13](-[n:14]3[cH:15][cH:16][n:17][cH:18]3)[cH:19][cH:20]2)[CH2:21][CH2:22]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([O:9][c:10]2[cH:11][cH:12][c:13](-[n:14]3[cH:15][cH:16][n:17][cH:18]3)[cH:19][... | CCC[CH2][Sn]([Cl])([Cl])[CH2]CCC.c1cn(-c2ccc(OC3CCNCC3)cc2)cn1 | CC(C)CN1CCC(Oc2ccc(-n3ccnc3)cc2)CC1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | c5453a8b22dde1752bbee9d938fa6c1b29b157df3ee3efeb36640e89adbe6533 | 92c4050b7b70356e79fb7d199a0bcda4cb4fb71f721dd8f555006485a88111eb | c1cn(-c2ccc(OC3CCNCC3)cc2)cn1 | C-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[Sn](-[Cl])(-[Cl])-[CH2]-C-C-[CH3;D1;+0:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:3]-[CH;D3;+0:2](-[CH3;D1;+0:4])-[CH3;D1;+0:1])-[C:8]-[C:9] | null | [] | null | null | 16 | HOUR | A solution of the product of Example 6 (130 mg), cyclohexanone (0.06 mL), and dibutyltin dichloride (3 mg) in THF (0.1 mL) was treated with phenylsilane (0.07 mL). After 16 h, the resulting mixture was chromatographed (0-8% 2M methanolic ammonia/DCM), giving the title compound as a waxy solid (18 mg). 1H NMR (400 MHz, ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Tin | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1c[nH]cn1 | HCl.Sn | C1CCOC1 | null | 16 | CCC[CH2][Sn]([Cl])([Cl])[CH2]CCC.c1cn(-c2ccc(OC3CCNCC3)cc2)cn1>C1CCOC1>CC(C)CN1CCC(Oc2ccc(-n3ccnc3)cc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8fad9727d68f44a9901ab1ec5c51fcfb | CC(C)C=O.CCC[CH2][Sn]([Cl])([Cl])[CH2]CCC.c1cn(-c2ccc(OC3CCNCC3)cc2)cn1>>c1cn(-c2ccc(OC3CCN(C4CCCC4)CC3)cc2)cn1 | N1(C=NC=C1)C1=CC=C(OC2CCNCC2)C=C1.C(C(C)C)=O.C(CCC)[Sn](CCCC)(Cl)Cl.C1(=CC=CC=C1)[SiH3]>>C1(CCCC1)N1CCC(CC1)OC1=CC=C(C=C1)N1C=NC=C1 | C[CH:17]([CH:13]=O)[CH3:14].CCC[CH2][Sn]([Cl])([Cl])[CH2]C[CH2:16][CH3:15].[cH:1]1[cH:2][n:3](-[c:4]2[cH:5][cH:6][c:7]([O:8][CH:9]3[CH2:10][CH2:11][NH:12][CH2:18][CH2:19]3)[cH:20][cH:21]2)[cH:22][n:23]1>>[cH:1]1[cH:2][n:3](-[c:4]2[cH:5][cH:6][c:7]([O:8][CH:9]3[CH2:10][CH2:11][N:12]([CH:13]4[CH2:14][CH2:15][CH2:16][CH2:... | CC(C)C=O.CCC[CH2][Sn]([Cl])([Cl])[CH2]CCC.c1cn(-c2ccc(OC3CCNCC3)cc2)cn1 | c1cn(-c2ccc(OC3CCN(C4CCCC4)CC3)cc2)cn1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 3e5326fa41f36adea6aacee576b720dc36b92c0952de7bdf859daff8cbf3d9a4 | 2aaed6d073b4fd8753dfdb27d6b51aa16006392671408dbe672ad3d6f8fa14f6 | c1cn(-c2ccc(OC3CCN(C4CCCC4)CC3)cc2)cn1 | C-C-C-[CH2]-[Sn](-[Cl])(-[Cl])-[CH2]-C-[CH2;D2;+0:1]-[CH3;D1;+0:2].C-[CH;D3;+0:3](-[CH3;D1;+0:4])-[CH;D2;+0:5]=O.[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[CH;D3;+0:5]1-[CH2;D2;+0:4]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[CH2;D2;+0:3]-1)-[C:9]-[C:10] | null | [] | null | null | 16 | HOUR | A solution of the product of Example 6 (130 mg), isobutyraldehyde (0.06 mL), and dibutyltin dichloride (3 mg) in THF (0.1 mL) was treated with phenylsilane (0.07 mL). After 16 h, the resulting mixture was chromatographed (0-8% 2M methanolic ammonia/DCM), giving the title compound as a waxy solid (57 mg). 1H NMR (400 MH... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine.Tin | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1.C1CCCC1 | c1c[nH]cn1.c1ccccc1.C1CC[NH]CC1.C1CCCC1 | HCl.Sn | C1CCOC1 | null | 16 | CC(C)C=O.CCC[CH2][Sn]([Cl])([Cl])[CH2]CCC.c1cn(-c2ccc(OC3CCNCC3)cc2)cn1>C1CCOC1>c1cn(-c2ccc(OC3CCN(C4CCCC4)CC3)cc2)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc38c2af609146af82a40efe6716b1ba | CC(C)(C)OC(=O)N1CCC(O)CC1.CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C.Oc1ccc(-c2ccccc2)cc1>>N.c1ccc(-c2ccc(OC3CCNCC3)cc2)cc1 | OC1CCN(CC1)C(=O)OC(C)(C)C.C1(=CC=CC=C1)C1=CC=C(C=C1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Cl)Cl.N(=NC(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>N.C(Cl)Cl.C1(=CC=C(C=C1)OC1CCNCC1)C1=CC=CC=C1 | CC(C)(C)OC(=O)[N:17]1[CH2:16][CH2:15][CH:14]([OH:13])[CH2:19][CH2:18]1.CC(C)(C)OC(=O)N=[N:4]C(=O)OC(C)(C)C.O[c:12]1[cH:11][cH:10][c:9](-[c:8]2[cH:7][cH:6][cH:5][cH:23][cH:22]2)[cH:21][cH:20]1>>[NH3:4].[cH:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([O:13][CH:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)[cH:20][cH:... | CC(C)(C)OC(=O)N1CCC(O)CC1.CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C.Oc1ccc(-c2ccccc2)cc1 | N.c1ccc(-c2ccc(OC3CCNCC3)cc2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | fe7e504d552b31842d25f2c9c0e3e359bfac598abef74c57c464b9a7d9eef99d | fffd8854affd038b0da6a0ed69aea71c9302d200efe0a706572ca9c6fcfe89ad | c1ccc(-c2ccc(OC3CCNCC3)cc2)cc1 | C-C(-C)(-C)-O-C(=O)-N=[N;H0;D2;+0:1]-C(=O)-O-C(-C)(-C)-C.C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:2]1-[C:3]-[C:4]-[C:5](-[OH;D1;+0:6])-[C:7]-[C:8]-1.O-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[NH3;D0;+0:1].[c:11]:[c:10]:[c;H0;D3;+0:9](-[O;H0;D2;+0:6]-[C:5]1-[C:4]-[C:3]-[NH;D2;+0:2]-[C:8]-[C:7]-1):[c:12]:[c:13] | 1 | [{"value": 1.0, "product": "N.C(Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A suspension of tert-butyl 4-hydroxy-1-piperidine carboxylate (497 mg), 4-phenylphenol (300 mg), and polymer-supported triphenylphosphine (1.2 g) in DCM (10 mL) was treated with di-tert-butyl azodicarboxylate (608 mg). The resulting mixture was shaken for 16 h, and filtered through a pad of celite. The pad was washed w... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Ether.Ether.Diazene.Secondary alcohol.Aromatic alcohol.Boc.Boc.Boc | Ether.Secondary amine | C1CC[NH]CC1.c1ccccc1 | c1ccccc1.C1CCNCC1 | c1ccccc1.c1ccccc1.C1CCNCC1 | HO- | null | null | 16 | CC(C)(C)OC(=O)N1CCC(O)CC1.CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C.Oc1ccc(-c2ccccc2)cc1>>N.c1ccc(-c2ccc(OC3CCNCC3)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a7df8718c86049db81c9d8953d000404 | CCOC=O.N#CCC1CCCC1>>N#CC(C=O)C1CCCC1 | C1(CCCC1)CC#N.CCCCC.C(=O)OCC>>C1(CCCC1)C(C=O)C#N | CCO[CH:4]=[O:5].[N:1]#[C:2][CH2:3][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1>>[N:1]#[C:2][CH:3]([CH:4]=[O:5])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1 | CCOC=O.N#CCC1CCCC1 | N#CC(C=O)C1CCCC1 | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 3dc7150b54f968d08b04811ce6d9fd58ce6b1717b4fbd76dbd02e91654c50b43 | 2aa39a25981921b5291a5742361ce4441cd47a0f2b930c869f26329c906b19c5 | C1CCCC1 | C-C-O-[CH;D2;+0:1]=[O;D1;H0:2].[C:3]-[C:4](-[CH2;D2;+0:5]-[C:6]#[N;D1;H0:7])-[C:8]>>[C:3]-[C:4](-[CH;D3;+0:5](-[C:6]#[N;D1;H0:7])-[CH;D2;+0:1]=[O;D1;H0:2])-[C:8] | null | [] | -60 | CELSIUS | 10 | MINUTE | A mixture of 2-cyclopentylacetonitrile (0.50 g, 4.59 mmol) in tetrahydrofuran (10 mL) was cooled to −60° C. then treated with 1.7 M tert-buytllithium in pentane (3.25 mL, 5.50 mmol) while maintaining the reaction temperature at less than −55° C. The solution was stirred for 10 minutes then ethyl formate (0.41 g, 5.50 m... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aldehyde | null | null | C1CCCC1 | HO- | O1CCCC1 | -60 | 0.166667 | CCOC=O.N#CCC1CCCC1>O1CCCC1>N#CC(C=O)C1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9a2b2b67968740b09716865dce6a705d | N#CCBr.Nc1ccc(Oc2ccccc2)cc1>>N#CCNc1ccc(Oc2ccccc2)cc1 | BrCC#N.O(C1=CC=CC=C1)C1=CC=C(N)C=C1.BrCC#N.C(C)N(CC)CC>>O(C1=CC=CC=C1)C1=CC=C(NCC#N)C=C1 | Br[CH2:3][C:2]#[N:1].[NH2:4][c:5]1[cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1>>[N:1]#[C:2][CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][cH:17]1 | N#CCBr.Nc1ccc(Oc2ccccc2)cc1 | N#CCNc1ccc(Oc2ccccc2)cc1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(Oc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 45 | [{"value": 45.0, "product": "O(C1=CC=CC=C1)C1=CC=C(NCC#N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.8, "product": "O(C1=CC=CC=C1)C1=CC=C(NCC#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | A mixture of 4-phenoxyaniline (7.0 g, 37.8 mmol), bromoacetonitrile (4.5 g, 37.8 mmol) and triethylamine (4.2 g, 41.6 mmol) in tetrahydrofuran (50 mL) was heated at 85° C. for 5.25 hours then cooled and another portion of bromoacetonitrile (6.5 g, 5.46 mmol) was added. The mixture was heated at 85° C. for 18 hours then... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HBr | O1CCCC1 | 85 | null | N#CCBr.Nc1ccc(Oc2ccccc2)cc1>O1CCCC1>N#CCNc1ccc(Oc2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7a119e6b380e48b1928402a388d28815 | N#Cc1c(N)c(C2CCCC2)cn1-c1ccc(Oc2ccccc2)cc1.N=CN>>Nc1ncnc2c(C3CCCC3)cn(-c3ccc(Oc4ccccc4)cc3)c12 | NC1=C(N(C=C1C1CCCC1)C1=CC=C(C=C1)OC1=CC=CC=C1)C#N.C(C)(=O)O.C(=N)N>>C1(CCCC1)C1=CN(C2=C1N=CN=C2N)C2=CC=C(C=C2)OC2=CC=CC=C2 | [N:1]#[C:2][c:28]1[c:6]([NH2:5])[c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12]2)[cH:13][n:14]1-[c:15]1[cH:16][cH:17][c:18]([O:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[cH:26][cH:27]1.N[CH:4]=[NH:3]>>[NH2:1][c:2]1[n:3][cH:4][n:5][c:6]2[c:7]([CH:8]3[CH2:9][CH2:10][CH2:11][CH2:12]3)[cH:13][n:14](-[c:15]3[cH:16][cH:17]... | N#Cc1c(N)c(C2CCCC2)cn1-c1ccc(Oc2ccccc2)cc1.N=CN | Nc1ncnc2c(C3CCCC3)cn(-c3ccc(Oc4ccccc4)cc3)c12 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | f19dbf5d03a6825dd5f8c304f8d6f3418a6ebdaf9f0b55bd20edc2f3f8ce34be | 1aa7191beb21c0c960b18631a0bd52edc8e0a5e54fb7edd4fc42913ae18d9901 | c1ccc(Oc2ccc(-n3cc(C4CCCC4)c4ncncc43)cc2)cc1 | N-[CH;D2;+0:1]=[NH;D1;+0:2].[N;H0;D1;+0:3]#[C;H0;D2;+0:4]-[c:5]1:[#7;a:6](-[c:7]):[c:8]:[c:9]:[c:10]:1-[NH2;D1;+0:11]>>[NH2;D1;+0:3]-[c;H0;D3;+0:4]1:[n;H0;D2;+0:2]:[cH;D2;+0:1]:[n;H0;D2;+0:11]:[c:10]2:[c:9]:[c:8]:[#7;a:6](-[c:7]):[c:5]:2:1 | 73 | [{"value": 73.0, "product": "C1(CCCC1)C1=CN(C2=C1N=CN=C2N)C2=CC=C(C=C2)OC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.6, "product": "C1(CCCC1)C1=CN(C2=C1N=CN=C2N)C2=CC=C(C=C2)OC2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | A mixture of the 3-amino-4-cyclopentyl-1-(4-phenoxyphenyl)-1H-2-pyrrolecarbonitrile (185 mg, 0.539 mmol) in absolute ethanol (10 mL) was treated with formamidine acetate (450 mg, 4.33 mmol) then heated at 85° C. for 2 hours. The solvent was evaporated under reduced pressure then the residue was purified by preparative ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine.Primary amine | Primary amine | c1cc[nH]c1 | c1c[nH]c2cncnc12 | C1CCCC1.c1c[nH]c2cncnc12.c1ccccc1.c1ccccc1 | Other | C(C)O | 85 | null | N#Cc1c(N)c(C2CCCC2)cn1-c1ccc(Oc2ccccc2)cc1.N=CN>C(C)O>Nc1ncnc2c(C3CCCC3)cn(-c3ccc(Oc4ccccc4)cc3)c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3ea04bd552ac4d0fbd04f91758f9a726 | N#Cc1ccn(C2CCCC2)c1C=O.NN>>Nc1nncc2c1ccn2C1CCCC1 | C1(CCCC1)N1C(=C(C=C1)C#N)C=O.Cl.Cl.NN>>C1(CCCC1)N1C=CC=2C1=CN=NC2N | O=[CH:5][c:6]1[c:7]([C:2]#[N:1])[cH:8][cH:9][n:10]1[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1.[NH2:3][NH2:4]>>[NH2:1][c:2]1[n:3][n:4][cH:5][c:6]2[c:7]1[cH:8][cH:9][n:10]2[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1 | N#Cc1ccn(C2CCCC2)c1C=O.NN | Nc1nncc2c1ccn2C1CCCC1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 377eac503eaf096d8edd56661268db2947dc5624a15c5ab2472e3e0e61e27ee4 | fa59c52dd5da416f757f65367be99eabbf642b5454b61e6f56bbb37a09927483 | c1cn(C2CCCC2)c2cnncc12 | O=[CH;D2;+0:1]-[c:2]1:[#7;a:3](-[C:4]):[c:5]:[c:6]:[c:7]:1-[C;H0;D2;+0:8]#[N;H0;D1;+0:9].[NH2;D1;+0:10]-[NH2;D1;+0:11]>>[C:4]-[#7;a:3]1:[c:5]:[c:6]:[c:7]2:[c:2]:1:[cH;D2;+0:1]:[n;H0;D2;+0:11]:[n;H0;D2;+0:10]:[c;H0;D3;+0:8]:2-[NH2;D1;+0:9] | null | [] | null | null | null | null | A mixture of 1-cyclopentyl-2-formyl-1H-3-pyrrolecarbonitrile (0.525 g, 2.79 mmol) and hydrazine dihydrochloride (0.35 g, 3.35 mmol) in ethanol (30 mL) was heated at reflux for 2.5 hours then cooled to ambient temperature and purified by preparative reverse phase HPLC to give the title compound as a hydroscopic glass co... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aldehyde.Nitrile | Primary amine | c1c[nH]cc1 | c1nncc2[nH]ccc12 | c1nncc2[nH]ccc12.C1CCCC1 | HO- | C(C)O | null | null | N#Cc1ccn(C2CCCC2)c1C=O.NN>C(C)O>Nc1nncc2c1ccn2C1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a4b076179dca456485413d3e1e416279 | BrBr.Nc1nncc2c1ccn2C1CCCC1>>Nc1nncc2c1c(Br)cn2C1CCCC1 | BrBr.C1(CCCC1)N1C=CC=2C1=CN=NC2N.BrBr.[OH-].[Na+].O>>BrC1=CN(C2=CN=NC(=C21)N)C2CCCC2 | Br[Br:9].[NH2:1][c:2]1[n:3][n:4][cH:5][c:6]2[c:7]1[cH:8][cH:10][n:11]2[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1>>[NH2:1][c:2]1[n:3][n:4][cH:5][c:6]2[c:7]1[c:8]([Br:9])[cH:10][n:11]2[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | BrBr.Nc1nncc2c1ccn2C1CCCC1 | Nc1nncc2c1c(Br)cn2C1CCCC1 | null | null | ClCCl | Functional Group Interconversion | Bromination | e8a70d132c5b93ca409b6111f13d0cba041e6984c4f07d40dc0d4a3acc6a74ba | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cn(C2CCCC2)c2cnncc12 | Br-[Br;H0;D1;+0:1].[C:2]-[#7;a:3]1:[c:4]:[cH;D2;+0:5]:[c:6]2:[c:7](-[N;D1;H2:8]):[#7;a:9]:[#7;a:10]:[c:11]:[c:12]:1:2>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:5]1:[c:4]:[#7;a:3](-[C:2]):[c:12]2:[c:11]:[#7;a:10]:[#7;a:9]:[c:7](-[N;D1;H2:8]):[c:6]:2:1 | 35 | [{"value": 35.0, "product": "BrC1=CN(C2=CN=NC(=C21)N)C2CCCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.0, "product": "BrC1=CN(C2=CN=NC(=C21)N)C2CCCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 1-cyclopentyl-1H-pyrrolo[2,3-d]pyridazin-4-amine (0.595 mg, approx. 60% pure, 1.76 mmol) in dichloromethane (100 mL) was treated with a solution of dichloromethane (5 mL) containing bromine (0.5 g, 2.95 mmol) over the course of 1.25 hours. The mixture was stirred an additional one hour then another portion... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1nncc2[nH]ccc12 | c1c[nH]c2cnncc12 | c1c[nH]c2cnncc12.C1CCCC1 | HBr | ClCCl | null | 1 | BrBr.Nc1nncc2c1ccn2C1CCCC1>ClCCl>Nc1nncc2c1c(Br)cn2C1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4ee0e95287a3428ba9b400d4a0569d2f | Nc1nncc2c1c(Br)cn2C1CCCC1>>Nc1nncc2c1c(-c1ccc(Oc3ccccc3)cc1)cn2C1CCCC1 | BrC1=CN(C2=CN=NC(=C21)N)C2CCCC2.O(C1=CC=CC=C1)C1=CC=C(C=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>C1(CCCC1)N1C=C(C=2C1=CN=NC2N)C2=CC=C(C=C2)OC2=CC=CC=C2.O(C1=CC=CC=C1)C1=CC=C(C=C1)B(O)O | Br[c:8]1[c:7]2[c:2]([NH2:1])[n:3][n:4][cH:5][c:6]2[n:23]([CH:24]2[CH2:25][CH2:26][CH2:9][CH2:28]2)[cH:22]1>>[NH2:1][c:2]1[n:3][n:4][cH:5][c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[cH:20][cH:21]1)[cH:22][n:23]2[CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28]1 | Nc1nncc2c1c(Br)cn2C1CCCC1 | Nc1nncc2c1c(-c1ccc(Oc3ccccc3)cc1)cn2C1CCCC1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O.COCCOC | Aromatic Heterocycle Formation | OtherReaction | f27a42616b1c67cdcd393f1a4700264031759bc4e8cecd2cb09f5db1c966dbe3 | a4840aa8bdfd6f728c7dfa6c00c462c0316cfea6c6529f068981467c19c289cb | c1ccc(Oc2ccc(-c3cn(C4CCCC4)c4cnncc34)cc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3](-[C:4]2-[C:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-2):[c:9]2:[c:10]:[#7;a:11]:[#7;a:12]:[c:13](-[N;D1;H2:14]):[c:15]:2:1>>[N;D1;H2:14]-[c:13]1:[#7;a:12]:[#7;a:11]:[c:10]:[c:9]2:[#7;a:3](-[C:4]3-[C:5]-[CH2;D2;+0:6]-[C:16]-[CH2;D2;+0:8]-3):[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[c:17... | null | [] | 85 | CELSIUS | null | null | A mixture of 3-bromo-1-cyclopentyl-1H-pyrrolo [2,3-d]pyridazin-4-amine (0.057 g, 0.178 mmol), 4-phenoxyphenyl boronic acid (0.057 g, 0.266 mmol), sodium carbonate (0.062 g, 0.588 mmol) and tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.011 mmol) in ethylene glycol dimethyl ether (3 mL) and water (1.5 mL) was heated... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1c[nH]c2cnncc12.C1CCCC1 | c1ccccc1.c1ccccc1.c1c[nH]c2cnncc12.C1CCCC1 | c1ccccc1.c1ccccc1.c1c[nH]c2cnncc12.C1CCCC1 | Br- | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC | 85 | null | Nc1nncc2c1c(Br)cn2C1CCCC1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O.COCCOC>Nc1nncc2c1c(-c1ccc(Oc3ccccc3)cc1)cn2C1CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9dc90570bed3454eaea2d745c410f728 | CC(C)c1cccc(B(O)O)c1.Clc1cnccn1>>CC(C)c1cccc(-c2cnccn2)c1 | C(C)(C)C=1C=C(C=CC1)B(O)O.ClC1=NC=CN=C1>>C(C)(C)C=1C=C(C=CC1)C1=NC=CN=C1 | OB(O)[c:8]1[cH:7][cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:15]1.Cl[c:9]1[cH:10][n:11][cH:12][cH:13][n:14]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][c:8](-[c:9]2[cH:10][n:11][cH:12][cH:13][n:14]2)[cH:15]1 | CC(C)c1cccc(B(O)O)c1.Clc1cnccn1 | CC(C)c1cccc(-c2cnccn2)c1 | null | C1=CC=C(C=C1)P(CCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.C1=CC=C(C=C1)P(CCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.[Pd] | C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | f4f2599a1f2d23f122d9e68430d5dc3c8a9f800f7adcc4136d8b17b1c1c7d091 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cnccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[c:9]:[c:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:10]:[c:11] | null | [] | 80 | CELSIUS | null | null | To a solution of commercial 3-isopropyl-benzene boronic acid (1.0 g) in a 2:2:1 mixture of toluene/1M Na2CO3/EtOH (122 mL), at r.t.,2-chloropyrazine (599 μL) and the bis[1.2-bis(diphenylphosphino)ethane]-palladium(0) catalyst (110 mg) were added. The reaction mixture was heated at 80° C. for 3 hr. It was then cooled do... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1cnccn1 | c1ccccc1.c1cnccn1 | c1ccccc1.c1cnccn1 | HCl.B | C1=CC=C(C=C1)P(CCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.C1=CC=C(C=C1)P(CCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.[Pd].C1(=CC=CC=C1)C | 80 | null | CC(C)c1cccc(B(O)O)c1.Clc1cnccn1>C1=CC=C(C=C1)P(CCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.C1=CC=C(C=C1)P(CCP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4.[Pd].C1(=CC=CC=C1)C>CC(C)c1cccc(-c2cnccn2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6ed8d70bbdac4fe6b1078c53aeb4a3c9 | Cc1cc(F)ccc1-c1cnccn1>>Cc1cc(F)ccc1C1CNCCN1 | FC1=CC(=C(C=C1)C1=NC=CN=C1)C.Cl>>Cl.FC1=CC(=C(C=C1)C1NCCNC1)C | [CH3:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][c:8]1-[c:9]1[cH:10][n:11][cH:12][cH:13][n:14]1>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][c:8]1[CH:9]1[CH2:10][NH:11][CH2:12][CH2:13][NH:14]1 | Cc1cc(F)ccc1-c1cnccn1 | Cc1cc(F)ccc1C1CNCCN1 | null | [OH-].[OH-].[Pd+2] | CCO | Reduction | OtherReaction | e72d5c9669dbcc55202ef34c029b3b23b6c11bcbe31d528c7e902f249a9de774 | 37c66050709a4b09cbaa1fadc57d86c6aebd0e9d91c855b62287cbfd7cec4ba8 | c1ccc(C2CNCCN2)cc1 | [C;D1;H3:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[n;H0;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[n;H0;D2;+0:10]:1):[c:11]:[c:12]>>[C;D1;H3:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[NH;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-[NH;D2;+0:10]-1):[c:11]:[c:12] | null | [] | null | null | null | null | 2-(4-Fluoro-2-methyl-phenyl)-pyrazine (0.3 g) dissolved in EtOH 95% (20 mL) and 37% HCl (0.2 mL) was hydrogenated at 5 atm. for 4 hr, in the presence of 20% Pd(OH)2/C (30 mg) as catalyst. The catalyst was filtered off and the solvent was evaporated. The crude residue was triturated in MeOH/AcOEt (5 mL/15 mL) to obtain ... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine.Secondary amine | c1cnccn1 | C1CNCCN1 | c1ccccc1.C1CNCCN1 | null | [OH-].[OH-].[Pd+2].CCO | null | null | Cc1cc(F)ccc1-c1cnccn1>[OH-].[OH-].[Pd+2].CCO>Cc1cc(F)ccc1C1CNCCN1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-42dec859f6094151b0c7725b2666b1ad | O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.O=C1NCCNC1c1ccccc1>>O=C1NCCN(C(=O)Cl)C1c1ccccc1 | ClC(Cl)(OC(OC(Cl)(Cl)Cl)=O)Cl.C1(=CC=CC=C1)C1C(NCCN1)=O>>O=C1C(N(CCN1)C(=O)Cl)C1=CC=CC=C1 | ClC(Cl)(Cl)O[C:7](OC(Cl)(Cl)[Cl:9])=[O:8].[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][NH:6][CH:10]1[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][N:6]([C:7](=[O:8])[Cl:9])[CH:10]1[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.O=C1NCCNC1c1ccccc1 | O=C1NCCN(C(=O)Cl)C1c1ccccc1 | null | null | C(Cl)Cl | Acylation | OtherReaction | e42e57261b542adf323d2424161de7351c671a80c841d9853044e323ae3b735d | c5674cad8f50e137418323e673c87f500d3f14758d6a3111a9ca9e5c866850a2 | O=C1NCCNC1c1ccccc1 | Cl-C(-Cl)(-Cl)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-O-C(-Cl)(-Cl)-[Cl;H0;D1;+0:3].[O;D1;H0:4]=[C:5]1-[#7:6]-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-1-[c:11]>>[Cl;H0;D1;+0:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:5](=[O;D1;H0:4])-[C:10]-1-[c:11] | 56.4 | [{"value": 56.4, "product": "O=C1C(N(CCN1)C(=O)Cl)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred solution of triphosgene (0.558 g) in DCM (10 ml) pyridine (0.46 mL) was added at 0° C. and, after 10 min, 3-phenyl-piperazine-2-one (1 g). The ice bath was removed and the mixture was stirred at room temperature overnight. The mixture was concentrated and the product was purified by flash chromatography (C... | 10.6084/m9.figshare.5104873.v1 | null | Trichloro group.Trichloro group.Carbonic Ester.Secondary amine | Acyl halide.Tertiary amide | C1CNCCN1 | C1C[NH]CCN1 | C1C[NH]CCN1.c1ccccc1 | HCl | C(Cl)Cl | null | 8 | O=C(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.O=C1NCCNC1c1ccccc1>C(Cl)Cl>O=C1NCCN(C(=O)Cl)C1c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-85427b73764646c9b92cca818977921d | C[Si](C)(C)C=[N+]=[N-].O=C(O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>>COC(=O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | C[Si](C)(C)C=[N+]=[N-].FC(C=1C=C(C(=O)O)C=C(C1)C(F)(F)F)(F)F>>COC(C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O | C[Si](C)(C)[CH:1]=[N+]=[N-].[OH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18]1 | C[Si](C)(C)C=[N+]=[N-].O=C(O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | COC(=O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | C1(=CC=CC=C1)C.CO | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 39589be0e9a30df66714fe618d22a8ac0fb24901dbf2ead1ab33e31556c7ac64 | 8b539baf7aeb5ab868833e33306bad77200a853d562904197e13de2e27e229d7 | c1ccccc1 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | null | [] | 0 | CELSIUS | 1 | HOUR | Trimethylsilyldiazomethane (11.5 mL) was added drop-wise to a solution of 3,5-bis-(trifluoromethyl)benzoic acid (2 g) in dry toluene (20 mL) and methanol (0.5 mL) previously cooled to 0° C. under a nitrogen atmosphere. The solution was stirred at r.t. for 1 hr, then concentrated in vacuo to give 3,5-bis-(trifluoromethy... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo.Silyl protective group | Ester | null | null | c1ccccc1 | Other | C1(=CC=CC=C1)C.CO | 0 | 1 | C[Si](C)(C)C=[N+]=[N-].O=C(O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>C1(=CC=CC=C1)C.CO>COC(=O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8ae11a41d865478e840482f4273371ed | COC(=O)C(C)(C)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>>CC(C)(C(=O)O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | Cl.FC(C=1C=C(C=C(C1)C(F)(F)F)C(C(=O)OC)(C)C)(F)F.[OH-].[K+]>>FC(C=1C=C(C=C(C1)C(F)(F)F)C(C(=O)O)(C)C)(F)F | C[O:6][C:4]([C:2]([CH3:1])([CH3:3])[c:7]1[cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]1)=[O:5]>>[CH3:1][C:2]([CH3:3])([C:4](=[O:5])[OH:6])[c:7]1[cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][c:15]([C:16]([F:17])([F:18])[F:19])[cH:20]1 | COC(=O)C(C)(C)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | CC(C)(C(=O)O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | A solution of 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionic acid, methyl ester (intermediate 69-184 mg) and potassium hydroxide (131 mg) in MeOH (2.5 mL) was heated to reflux for 1 hour, then it was allowed to cool to r.t. and acidified to pH=3 with 10% hydrochloric acid solution and extracted with AcOEt (2×10 ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1 | Other | CO | null | null | COC(=O)C(C)(C)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>CO>CC(C)(C(=O)O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-35bdd3b1dd06456e91d478cc0db0ae3e | Cc1cc(F)ccc1[C@H]1CNCCN1.O=C(Cl)OCc1ccccc1>>Cc1cc(F)ccc1[C@H]1CN(C(=O)OCc2ccccc2)CCN1 | C(C1=CC=CC=C1)OC(=O)Cl.Cl.Cl.FC1=CC(=C(C=C1)[C@@H]1NCCNC1)C>>C(C1=CC=CC=C1)OC(=O)N1C[C@@H](NCC1)C1=C(C=C(C=C1)F)C | [CH3:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][c:8]1[C@H:9]1[CH2:10][NH:11][CH2:22][CH2:23][NH:24]1.Cl[C:12](=[O:13])[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][c:8]1[C@H:9]1[CH2:10][N:11]([C:12](=[O:13])[O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[C... | Cc1cc(F)ccc1[C@H]1CNCCN1.O=C(Cl)OCc1ccccc1 | Cc1cc(F)ccc1[C@H]1CN(C(=O)OCc2ccccc2)CCN1 | null | null | C(Cl)Cl | Protection | N-alkylation of secondary amines with alkyl halides | 4451143905f811374b7e4cef978840c2bcbd908fec8f94e9f20bbc2686e59370 | d86dc1e6d0e089b3444b62ddfcf4c4822bdac4b60e628553036562518c29adcd | O=C(OCc1ccccc1)N1CCN[C@@H](c2ccccc2)C1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:9]-[C:10]-[#7:5]-[C:6]-[C:7]-1 | null | [] | 0 | CELSIUS | 2 | HOUR | A solution of benzylchloroformate (376 μL) in dry DCM (20 mL) was added drop-wise to a solution of the 2-(S)-(4-fluoro-2-methyl-phenyl)-piperazine dihydrochloride (700 mg) and TEA (1.1 mL) in DCM (30 mL) previously cooled to 0° C. under a nitrogen atmosphere. The mixture was stirred at r.t. for 2 hrs, then washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amine | Carbamic ester | C1CNCCN1 | C1CNCC[NH]1 | c1ccccc1.C1CNCC[NH]1.c1ccccc1 | HCl | C(Cl)Cl | 0 | 2 | Cc1cc(F)ccc1[C@H]1CNCCN1.O=C(Cl)OCc1ccccc1>C(Cl)Cl>Cc1cc(F)ccc1[C@H]1CN(C(=O)OCc2ccccc2)CCN1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-694454ae10164c309a818a8eeef7f6af | CC(C)I.COC(=O)Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1>>COC(=O)C(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)C(C)C | C(C)(C)I.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].COC(CC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O.C(C)(C)I>>COC(C(C(C)C)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)=O | I[CH:20]([CH3:21])[CH3:22].[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([c:6]1[cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19]1)[CH:20]([CH3:21])[CH3:22] | CC(C)I.COC(=O)Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | COC(=O)C(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)C(C)C | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 8c44d57f8486d6bee1a0b83f6845f011ce41bc47981bdbe8dc66352f860486a8 | ae23b78d8cc9afe1235c3056fa58900d3a27e232dc891dd767f4195ab4ddcbb6 | c1ccccc1 | I-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH;D3;+0:8](-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3])-[c:9](:[c:10]):[c:11] | null | [] | 0 | CELSIUS | 30 | MINUTE | Sodium bis(trimethylsilyl) amide (1.0M in THF—177 μL) was added drop-wise to a solution of (3,5-bis-trifluoromethyl-phenyl)-acetic acid methyl ester (389 mg) in dry THF (2 mL) at 0° C., under nitrogen atmosphere. After ten minutes, isopropyl iodide (143 μL) was added and the reaction mixture was stirred at 0° C. for 30... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester | Ester | null | null | c1ccccc1 | HI | C1CCOC1 | 0 | 0.5 | CC(C)I.COC(=O)Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1>C1CCOC1>COC(=O)C(c1cc(C(F)(F)F)cc(C(F)(F)F)c1)C(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3075e11c84e842c1acd56b5278c1e549 | CN.O=Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1>>CN=Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | FC(C=1C=C(C=O)C=C(C1)C(F)(F)F)(F)F.CN>>FC(C=1C=C(C=NC)C=C(C1)C(F)(F)F)(F)F | [CH3:1][NH2:2].O=[CH:3][c:4]1[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1>>[CH3:1][N:2]=[CH:3][c:4]1[cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1 | CN.O=Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | CN=Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Addition of primary amines to aldehydes/thiocarbonyls | d409dfd3247abb6c1b1364aec380d25720f21e374fd2124063f2d2ce54d31c4f | 9b341044a5a058244685b0b956d33f593ccdcd7346fa1d8d7b98a302fd35b8a2 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[NH2;D1;+0:6]>>[C;D1;H3:5]-[N;H0;D2;+0:6]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | A solution of 3,5-bis(trifluoromethyl)-benzaldehyde (412 μL) in dry THF (5 mL) was added dropwise to a solution of methylamine (2M in MeOH—3.12 mL) in dry THF (5 mL) at 23° C. under a nitrogen atmosphere. The reaction mixture was stirred overnight, then the solvent was evaporated in vacuo to give the title compound (38... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Substituted imine | null | null | c1ccccc1 | HO- | C1CCOC1 | null | 8 | CN.O=Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1>C1CCOC1>CN=Cc1cc(C(F)(F)F)cc(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-891a97e306d4495992d9116c500348f2 | Cc1cc(F)ccc1[C@H]1C(=O)NCCN1C(=O)N(C)[C@H](C)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>>Cc1cc(F)ccc1[C@H]1CNCCN1C(=O)N(C)[C@H](C)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | C(=O)(O)[O-].[Na+].FC(C=1C=C(C=C(C1)C(F)(F)F)[C@@H](C)N(C(=O)N1[C@H](C(NCC1)=O)C1=C(C=C(C=C1)F)C)C)(F)F.B.C1CCOC1.Cl>>FC(C=1C=C(C=C(C1)C(F)(F)F)[C@@H](C)N(C(=O)N1[C@H](CNCC1)C1=C(C=C(C=C1)F)C)C)(F)F | O=[C:10]1[C@H:9]([c:8]2[c:2]([CH3:1])[cH:3][c:4]([F:5])[cH:6][cH:7]2)[N:14]([C:15](=[O:16])[N:17]([CH3:18])[C@H:19]([CH3:20])[c:21]2[cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34]2)[CH2:13][CH2:12][NH:11]1>>[CH3:1][c:2]1[cH:3][c:4]([F:5])[cH:6][cH:7][c:8]1[C@H:9]1[CH2:10][N... | Cc1cc(F)ccc1[C@H]1C(=O)NCCN1C(=O)N(C)[C@H](C)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | Cc1cc(F)ccc1[C@H]1CNCCN1C(=O)N(C)[C@H](C)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | null | O.C1CCOC1 | Reduction | Reduction of secondary amides to amines | b51112e31d2a8841c3f8da7b8557990b065c14a7b2c0de6d1b1989d541f5c0bd | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | O=C(NCc1ccccc1)N1CCNC[C@@H]1c1ccccc1 | O=[C;H0;D3;+0:1]1-[#7:2]-[C:3]-[C:4]-[#7:5](-[C:6](-[#7:7])=[O;D1;H0:8])-[C:9]-1-[c:10]>>[#7:7]-[C:6](=[O;D1;H0:8])-[#7:5]1-[C:4]-[C:3]-[#7:2]-[CH2;D2;+0:1]-[C:9]-1-[c:10] | 57.4 | [{"value": 57.4, "product": "FC(C=1C=C(C=C(C1)C(F)(F)F)[C@@H](C)N(C(=O)N1[C@H](CNCC1)C1=C(C=C(C=C1)F)C)C)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of intermediate 40a (15.6 g) in anhydrous THF (94 ml), at 0° C., under N2, BH3.THF 1M/THF (154 ml) was added. The solution was heated at reflux for 3 hr. HCl 37% (54 ml) was slowly added maintaining the reaction mixture in an ice-bath and the reaction mixture was stirred at rt for 1 hr. Water was then add... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | C1CNCC[NH]1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1.c1ccccc1 | Other | O.C1CCOC1 | null | 1 | Cc1cc(F)ccc1[C@H]1C(=O)NCCN1C(=O)N(C)[C@H](C)c1cc(C(F)(F)F)cc(C(F)(F)F)c1>O.C1CCOC1>Cc1cc(F)ccc1[C@H]1CNCCN1C(=O)N(C)[C@H](C)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a0ec281597b743318293b3929a95087b | COc1ccc(-c2cc3c(n2-c2ccccc2C)CCN(Cc2ccccc2)C3)cc1>>COc1ccc(-c2cc3c(n2-c2ccccc2C)CCNC3)cc1 | C(C1=CC=CC=C1)N1CC2=C(CC1)N(C(=C2)C2=CC=C(C=C2)OC)C2=C(C=CC=C2)C>>COC1=CC=C(C=C1)C1=CC=2CNCCC2N1C1=C(C=CC=C1)C | c1ccc(C[N:21]2[CH2:20][CH2:19][c:10]3[c:9]([cH:8][c:7](-[c:6]4[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:24][cH:23]4)[n:11]3-[c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[CH3:18])[CH2:22]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]([n:11]2-[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[CH3:18])[CH2:19][CH2:20]... | COc1ccc(-c2cc3c(n2-c2ccccc2C)CCN(Cc2ccccc2)C3)cc1 | COc1ccc(-c2cc3c(n2-c2ccccc2C)CCNC3)cc1 | null | [OH-].[OH-].[Pd+2] | O1CCCC1.CO | Deprotection | Hydrogenolysis of tertiary amines | a30eaa236a81ef147f5f28e4d833ab14e33a5d35b9de7b2cf9c009f8aa08011d | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(-c2cc3c(n2-c2ccccc2)CCNC3)cc1 | [#7;a:1]:[c:2]1:[c:3]-[C:4]-[N;H0;D3;+0:5](-C-c2:c:c:c:c:c:2)-[C:6]-[C:7]-1>>[#7;a:1]:[c:2]1:[c:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]-1 | 98 | [{"value": 98.0, "product": "COC1=CC=C(C=C1)C1=CC=2CNCCC2N1C1=C(C=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.5, "product": "COC1=CC=C(C=C1)C1=CC=2CNCCC2N1C1=C(C=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 5-Benzyl-2-(4-methoxyphenyl)-1-(2-methylphenyl)4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine (5.6 g, 14 mmol; prepared by methods as described in Example 1) was added to a suspension of palladium hydroxide on carbon (20%, 1.52 g, 2 mmol) in dry methanol (130 mL) and tetrahydrofuran (100 mL) under argon. The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.c1cc2c(n1)CCNC2 | c1cc2c([nH]1)CCNC2 | c1ccccc1.c1ccccc1.c1cc2c([nH]1)CCNC2 | Other | [OH-].[OH-].[Pd+2].O1CCCC1.CO | null | 8 | COc1ccc(-c2cc3c(n2-c2ccccc2C)CCN(Cc2ccccc2)C3)cc1>[OH-].[OH-].[Pd+2].O1CCCC1.CO>COc1ccc(-c2cc3c(n2-c2ccccc2C)CCNC3)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7fc9c81abdff47de8db2aee8312afd71 | Cc1c2c(n(-c3ccccc3Cl)c1-c1ccc(Cl)cc1)CCNC2=O>>Cc1c2c(n(-c3ccccc3Cl)c1-c1ccc(Cl)cc1)CCNC2 | ClC1=C(C=CC=C1)N1C(=C(C=2C(NCCC21)=O)C)C2=CC=C(C=C2)Cl.CO>>ClC1=C(C=CC=C1)N1C(=C(C=2CNCCC21)C)C2=CC=C(C=C2)Cl | O=[C:24]1[c:3]2[c:2]([CH3:1])[c:13](-[c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]3)[n:5](-[c:6]3[cH:7][cH:8][cH:9][cH:10][c:11]3[Cl:12])[c:4]2[CH2:21][CH2:22][NH:23]1>>[CH3:1][c:2]1[c:3]2[c:4]([n:5](-[c:6]3[cH:7][cH:8][cH:9][cH:10][c:11]3[Cl:12])[c:13]1-[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1)[CH2:21]... | Cc1c2c(n(-c3ccccc3Cl)c1-c1ccc(Cl)cc1)CCNC2=O | Cc1c2c(n(-c3ccccc3Cl)c1-c1ccc(Cl)cc1)CCNC2 | null | null | O1CCCC1 | Reduction | Reduction of secondary amides to amines | 437c5db55f5f849f6a4e5360499407e96999484d6cddd734b0881e250538cd04 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(-c2cc3c(n2-c2ccccc2)CCNC3)cc1 | O=[C;H0;D3;+0:1]1-[#7:2]-[C:3]-[C:4]-[c:5]2:[#7;a:6](-[c:7]):[c:8]:[c:9]:[c:10]:2-1>>[c:7]-[#7;a:6]1:[c:8]:[c:9]:[c:10]2:[c:5]:1-[C:4]-[C:3]-[#7:2]-[CH2;D2;+0:1]-2 | 34.8 | [{"value": 34.8, "product": "ClC1=C(C=CC=C1)N1C(=C(C=2CNCCC21)C)C2=CC=C(C=C2)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1-(2-chlorophenyl)-2-(4-chlorophenyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (2.84 g, 7.64 mmol, prepared as in Scheme 2 and in a similar manner to Example 22) in tetrahydrofuran (38 mL) was added borane-tetrahydrofuran complex (1 M, 76 mL) at 0° C. over 20 minutes. The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | C1NCCc2[nH]ccc21 | c1cc2c([nH]1)CCNC2 | c1ccccc1.c1ccccc1.c1cc2c([nH]1)CCNC2 | Other | O1CCCC1 | null | null | Cc1c2c(n(-c3ccccc3Cl)c1-c1ccc(Cl)cc1)CCNC2=O>O1CCCC1>Cc1c2c(n(-c3ccccc3Cl)c1-c1ccc(Cl)cc1)CCNC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6e6784a81a91463a8f895bb1e9274f2a | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCNC3)cc1.CS(=O)(=O)Cl>>COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCN(S(C)(=O)=O)C3)cc1 | ClC1=C(C=CC=C1)N1C(=CC=2CNCCC21)C2=CC=C(C=C2)OC.CS(=O)(=O)Cl>>ClC1=C(C=CC=C1)N1C(=CC=2CN(CCC21)S(=O)(=O)C)C2=CC=C(C=C2)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]([n:11]2-[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl:18])[CH2:19][CH2:20][NH:21][CH2:26]3)[cH:27][cH:28]1.Cl[S:22]([CH3:23])(=[O:24])=[O:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]([n:11]2-[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl... | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCNC3)cc1.CS(=O)(=O)Cl | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCN(S(C)(=O)=O)C3)cc1 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | 3a2568ea67a50ab5e23bc11a629b46235140e4e3e9c40d4154c620903e696245 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | c1ccc(-c2cc3c(n2-c2ccccc2)CCNC3)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#7;a:5]:[c:6]1:[c:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#7;a:5]:[c:6]1:[c:7]-[C:8]-[N;H0;D3;+0:9](-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:10]-[C:11]-1 | 40 | [{"value": 40.0, "product": "ClC1=C(C=CC=C1)N1C(=CC=2CN(CCC21)S(=O)(=O)C)C2=CC=C(C=C2)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To an 8-mL vial charged with piperidinomethyl polystyrene (3.57 mmol/g, 99.2 mg, 0.354 mmol) and a solution of 1-(2-chlorophenyl)-2-(4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine (Example 2), 40.0 mg, 0.118 mmol) in 4 mL dichloromethane was added methanesulfonyl chloride (18.2 μL, 0.236 mmol). The react... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | c1cc2c([nH]1)CCNC2 | c1cc2c([nH]1)CCNC2 | c1ccccc1.c1ccccc1.c1cc2c([nH]1)CCNC2 | HCl | ClCCl | null | 4 | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCNC3)cc1.CS(=O)(=O)Cl>ClCCl>COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCN(S(C)(=O)=O)C3)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6799d787040d4ac2895b8f40a6daa6ba | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCNC3)cc1.O=C(Cl)c1cccc(Cl)c1>>COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCN(C(=O)c2cccc(Cl)c2)C3)cc1 | ClC1=C(C=CC=C1)N1C(=CC=2CNCCC21)C2=CC=C(C=C2)OC.ClC=1C=C(C(=O)Cl)C=CC1>>ClC=1C=C(C(=O)N2CC3=C(CC2)N(C(=C3)C3=CC=C(C=C3)OC)C3=C(C=CC=C3)Cl)C=CC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]([n:11]2-[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl:18])[CH2:19][CH2:20][NH:21][CH2:31]3)[cH:32][cH:33]1.Cl[C:22](=[O:23])[c:24]1[cH:25][cH:26][cH:27][c:28]([Cl:29])[cH:30]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]([n:11]2-[c:12]2[cH:... | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCNC3)cc1.O=C(Cl)c1cccc(Cl)c1 | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCN(C(=O)c2cccc(Cl)c2)C3)cc1 | null | null | ClCCl | Acylation | N-alkylation of secondary amines with alkyl halides | 29af23b4550a2433d66824e283c10763b6d571f521c33e8dc5eb8903d9dd7366 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCc2c(cc(-c3ccccc3)n2-c2ccccc2)C1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7]1:[c:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7;a:6]:[c:7]1:[c:8]-[C:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:11]-[C:12]-1 | 74 | [{"value": 74.0, "product": "ClC=1C=C(C(=O)N2CC3=C(CC2)N(C(=C3)C3=CC=C(C=C3)OC)C3=C(C=CC=C3)Cl)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.8, "product": "ClC=1C=C(C(=O)N2CC3=C(CC2)N(C(=C3)C3=CC=C(C=C3)OC)C3=C(C=CC=C3)Cl)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To an 8-mL vial charged with piperidinomethyl polystyrene (3.57 mmol/g, 198.4 mg, 0.708 mmol) and a solution of 1-(2-chlorophenyl)-2-(4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine (Example 2, 80.0 mg, 0.236 mmol) in 3 mL dichloromethane was added 3-chlorobenzoyl chloride (62.0 mg, 0.0.54 mmol). The reac... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | c1cc2c([nH]1)CCNC2 | c1cc2c([nH]1)CCNC2 | c1ccccc1.c1ccccc1.c1cc2c([nH]1)CCNC2.c1ccccc1 | HCl | ClCCl | null | 3 | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCNC3)cc1.O=C(Cl)c1cccc(Cl)c1>ClCCl>COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCN(C(=O)c2cccc(Cl)c2)C3)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6157255225ff4b5cbcd857cbe125149b | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCNC3)cc1.N#Cc1ccc(F)cc1>>COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCN(c2ccc(C#N)cc2)C3)cc1 | O.ClC1=C(C=CC=C1)N1C(=CC=2CNCCC21)C2=CC=C(C=C2)OC.C(=O)([O-])[O-].[K+].[K+].FC1=CC=C(C#N)C=C1>>ClC1=C(C=CC=C1)N1C(=CC=2CN(CCC21)C2=CC=C(C#N)C=C2)C2=CC=C(C=C2)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]([n:11]2-[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl:18])[CH2:19][CH2:20][NH:21][CH2:30]3)[cH:31][cH:32]1.F[c:22]1[cH:23][cH:24][c:25]([C:26]#[N:27])[cH:28][cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]([n:11]2-[c:12]2[cH:13][cH:14]... | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCNC3)cc1.N#Cc1ccc(F)cc1 | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCN(c2ccc(C#N)cc2)C3)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 98bcac89b32aa2b2766de9cac3f112509802dda7c2f349793518bb59d21a12ab | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(-c2cc3c(n2-c2ccccc2)CCN(c2ccccc2)C3)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7;a:6]:[c:7]1:[c:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[#7;a:6]:[c:7]1:[c:8]-[C:9]-[N;H0;D3;+0:10](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5])-[C:11]-[C:12]-1 | 43.1 | [{"value": 43.0, "product": "ClC1=C(C=CC=C1)N1C(=CC=2CN(CCC21)C2=CC=C(C#N)C=C2)C2=CC=C(C=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.1, "product": "ClC1=C(C=CC=C1)N1C(=CC=2CN(CCC21)C2=CC=C(C#N)C=C2)C2=CC=C(C=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 48 | HOUR | To a suspension of 1-(2-chlorophenyl)-2-(4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine (Example 2, 80.0 mg, 0.236 mmol) and K2CO3 (97.9 mg, 0.708 mmol) in 2 mL DMF was added 4-fluorobenzonitrile (86.0 mg, 0.472 mmol) under argon. The mixture was heated at 130° C. with stirring for 48 h. The mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cc2c([nH]1)CCNC2.c1ccccc1 | c1cc2c([nH]1)CCNC2.c1ccccc1 | c1ccccc1.c1ccccc1.c1cc2c([nH]1)CCNC2.c1ccccc1 | HF | CN(C)C=O | 130 | 48 | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCNC3)cc1.N#Cc1ccc(F)cc1>CN(C)C=O>COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCN(c2ccc(C#N)cc2)C3)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-59c2d44fd8294022b89c4269dbe6bbe8 | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCNC3)cc1.O=Cc1ccc(F)cc1>>COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCN(Cc2ccc(F)cc2)C3)cc1 | ClC1=C(C=CC=C1)N1C(=CC=2CNCCC21)C2=CC=C(C=C2)OC.FC1=CC=C(C=O)C=C1.C(C)(=O)O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].[OH-].[Na+]>>ClC1=C(C=CC=C1)N1C(=CC=2CN(CCC21)CC2=CC=C(C=C2)F)C2=CC=C(C=C2)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]([n:11]2-[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl:18])[CH2:19][CH2:20][NH:21][CH2:30]3)[cH:31][cH:32]1.O=[CH:22][c:23]1[cH:24][cH:25][c:26]([F:27])[cH:28][cH:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]([n:11]2-[c:12]2[cH:13][cH:14... | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCNC3)cc1.O=Cc1ccc(F)cc1 | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCN(Cc2ccc(F)cc2)C3)cc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | reductive amination | 646a2fc9876a66e5c3dd23cf2d7c8f8318244c05a5ce4ae33e5c1213861b4527 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | c1ccc(CN2CCc3c(cc(-c4ccccc4)n3-c3ccccc3)C2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]:[c:6]1:[c:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#7;a:5]:[c:6]1:[c:7]-[C:8]-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10]-[C:11]-1 | 97.6 | [{"value": 97.0, "product": "ClC1=C(C=CC=C1)N1C(=CC=2CN(CCC21)CC2=CC=C(C=C2)F)C2=CC=C(C=C2)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.6, "product": "ClC1=C(C=CC=C1)N1C(=CC=2CN(CCC21)CC2=CC=C(C=C2)F)C2=CC=C(C=C2)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-(2-chlorophenyl)-2-(4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine (Example 2, 677.7 mg, 0.50 mmol), 4-fluorobenzaldehyde (0.13 mL, 0.60 mmol), acetic acid (0.03 mL, 0.60 mmol), and NaBH(OAc)3 (148.4 mg, 0.70 mmol) in methylene chloride (15 mL) was stirred at rt for 24 h. Sodium hydroxide... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | c1cc2c([nH]1)CCNC2 | c1cc2c([nH]1)CCNC2 | c1ccccc1.c1ccccc1.c1cc2c([nH]1)CCNC2.c1ccccc1 | Other | C(Cl)Cl | null | null | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCNC3)cc1.O=Cc1ccc(F)cc1>C(Cl)Cl>COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCN(Cc2ccc(F)cc2)C3)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-293f4bd587b248f481c424a748897cdb | C1CCC2OC2C1.COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCNC3)cc1>>COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCN([C@@H]2CCCC[C@H]2O)C3)cc1 | ClC1=C(C=CC=C1)N1C(=CC=2CNCCC21)C2=CC=C(C=C2)OC.C12C(CCCC1)O2.C(C)N(CC)CC>>ClC1=C(C=CC=C1)N1C(=CC=2CN(CCC21)[C@H]2[C@@H](CCCC2)O)C2=CC=C(C=C2)OC | [CH:22]12[CH2:23][CH2:24][CH2:25][CH2:26][CH:27]1[O:28]2.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]([n:11]2-[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl:18])[CH2:19][CH2:20][NH:21][CH2:29]3)[cH:30][cH:31]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]3[c:10]([n:11]2-[c:12]2[cH:13][cH:14][c... | C1CCC2OC2C1.COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCNC3)cc1 | COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCN([C@@H]2CCCC[C@H]2O)C3)cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 669763d3d59100f79b0e1c9b6a21e4eb34626c345a144f0a758f4736c3c1a9c1 | 97e758d6c4c8255d25541eb6c6a6f62e7dc30829ea162ca3392731efabc98a65 | c1ccc(-c2cc3c(n2-c2ccccc2)CCN(C2CCCCC2)C3)cc1 | [#7;a:1]:[c:2]1:[c:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]-1.[C:8]1-[C:9]-[C:10]-[C:11]-[CH;D3;+0:12]2-[O;H0;D2;+0:13]-[CH;D3;+0:14]-1-2>>[#7;a:1]:[c:2]1:[c:3]-[C:4]-[N;H0;D3;+0:5](-[C@@H;D3;+0:14]2-[C:8]-[C:9]-[C:10]-[C:11]-[C@H;D3;+0:12]-2-[OH;D1;+0:13])-[C:6]-[C:7]-1 | 63 | [{"value": 63.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1-(2-chlorophenyl)-2-(4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine (Example 2, 500 mg, 1.33 mmol), cyclohexene oxide (1.34 mL, 13.3 mmol), and trietylamine (0.55 mL, 3.99 mmol) in ethanol (14 mL) was heated at reflux for 20 h. The solution was cooled to rt, and evaporated. The residue was... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine | Secondary alcohol.Tertiary amine | C1CCC2OC2C1.c1cc2c([nH]1)CCNC2 | c1cc2c([nH]1)CCNC2.C1CCCCC1 | c1ccccc1.c1ccccc1.c1cc2c([nH]1)CCNC2.C1CCCCC1 | null | C(C)O | null | null | C1CCC2OC2C1.COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCNC3)cc1>C(C)O>COc1ccc(-c2cc3c(n2-c2ccccc2Cl)CCN([C@@H]2CCCC[C@H]2O)C3)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d0cf7eeebaf94d0aba3dad3492e83406 | C=CC(=O)OC.NN1CCCCC1>>COC(=O)CCNN1CCCCC1 | NN1CCCCC1.C(C=C)(=O)OC>>N1(CCCCC1)NCCC(=O)OC | [CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH2:6].[NH2:7][N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][NH:7][N:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1 | C=CC(=O)OC.NN1CCCCC1 | COC(=O)CCNN1CCCCC1 | null | null | CO | Heteroatom Alkylation and Arylation | aza-Michael addition primary | 4a7280b3eca378a7e174ed7608bea18efb9ff5e7b0de5642dfc83fdcafa072ff | a32db21c2fbc4fea36d992580fcfff2a8264d071438edbd339d759c2c914b63b | C1CCNCC1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[C:7]-[#7:8](-[NH2;D1;+0:9])-[C:10]>>[C:7]-[#7:8](-[NH;D2;+0:9]-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[C;D1;H3:1])-[C:10] | 50.5 | [{"value": 50.5, "product": "N1(CCCCC1)NCCC(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.5, "product": "N1(CCCCC1)NCCC(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 1-aminopiperidine (100 g, 1.00 mol) in dry MeOH (1.00 L) at 0° C., methyl acrylate (99 mL, 1.10 mol) was added dropwise over 2 h. The resulting mixture was stirred overnight at rt. The solvents were evaporated, hexane was added to the residue, and white solid (impurity) was precipitated. The solid was ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ester.Vinyl | Hydrazine.Ester | null | null | C1CC[NH]CC1 | null | CO | null | 8 | C=CC(=O)OC.NN1CCCCC1>CO>COC(=O)CCNN1CCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a7f3b81c55c44181a9904755fcdbcc78 | CCOC(=O)CC(=O)N(CCC(=O)OC)N1CCCCC1>>CCOC(=O)C1C(=O)CCN(N2CCCCC2)C1=O | C(C)OC(CC(=O)N(CCC(=O)OC)N1CCCCC1)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>>O=C1N(CCC(C1C(=O)OCC)=O)N1CCCCC1 | CO[C:7](=[O:8])[CH2:9][CH2:10][N:11]([N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)[C:18]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:19]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[C:7](=[O:8])[CH2:9][CH2:10][N:11]([N:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[C:18]1=[O:19] | CCOC(=O)CC(=O)N(CCC(=O)OC)N1CCCCC1 | CCOC(=O)C1C(=O)CCN(N2CCCCC2)C1=O | null | null | CN(C)C=O.C1CCOC1 | Functional Group Interconversion | OtherReaction | 076c99fb8e1f07279e9954d28b83a2cf6b3e59e63bbf119695ed51e03379a58f | 6f130a746a78d10ca37f94948711de2b0c76f45052ca887b0e681c66276a7764 | O=C1CCN(N2CCCCC2)C(=O)C1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[#7:5](-[#7:6])-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]>>[#7:6]-[#7:5]1-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:9](-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13])-[C:7]-1=[O;D1;H0:8] | null | [] | 77 | CELSIUS | null | null | To a solution of methyl N-(3-ethoxy-3-oxopropanoyl)-N-(1-piperidinyl)-β-alaninate (43 g, 143 mmol) in a mixture of THF (2.26 L) and DMF (1.00 L) was added Cs2CO3 (140 g, 430 mmol). The resulting mixture was heated at reflux (77° C.) for 48 h. The cooled reaction was filtered, and the filtrate was evaporated. The filtra... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ketone | null | C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]CC1 | HO- | CN(C)C=O.C1CCOC1 | 77 | null | CCOC(=O)CC(=O)N(CCC(=O)OC)N1CCCCC1>CN(C)C=O.C1CCOC1>CCOC(=O)C1C(=O)CCN(N2CCCCC2)C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-68ade4b66e4b4b659a2a112d0fd74d5d | CCOC(=O)C1C(=O)CCN(N2CCCCC2)C1=O>>O=C1CCN(N2CCCCC2)C(=O)C1 | O=C1N(CCC(C1C(=O)OCC)=O)N1CCCCC1>>N1(C(CC(CC1)=O)=O)N1CCCCC1 | CCOC(=O)[CH:14]1[C:2](=[O:1])[CH2:3][CH2:4][N:5]([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[C:12]1=[O:13]>>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]([N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[C:12](=[O:13])[CH2:14]1 | CCOC(=O)C1C(=O)CCN(N2CCCCC2)C1=O | O=C1CCN(N2CCCCC2)C(=O)C1 | null | null | CC(=O)O | Reduction | Decarboxylation | 8fbe6375b12ffe41ffbcdf7408be0ba972c9810d9359e6d6596b942b093a6619 | f277909394d9f4e61cc2cdb65fef123102672ca91cfff7f8513cb0baf66138ac | O=C1CCN(N2CCCCC2)C(=O)C1 | C-C-O-C(=O)-[CH;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[#7:4](-[#7:5])-[C:6]-[C:7]-[C:8]-1=[O;D1;H0:9]>>[#7:5]-[#7:4]1-[C:6]-[C:7]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:1]-[C:2]-1=[O;D1;H0:3] | 22 | [{"value": 22.0, "product": "N1(C(CC(CC1)=O)=O)N1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}] | 125 | CELSIUS | null | null | Ethyl 2,4-dioxo-1,1′-bipiperidine-3-carboxylate (11.36 g, 42.38 mmol, Example 14) was dissolved in 10% AcOH (200 mL) and heated at reflux 125° C. for 1 h. The cooled reaction was evaporated, and the residue was purified by flash chromatography using a gradient of 9:1 to 1:1 CH2Cl2/acetone, to give the product as a yell... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]CC1 | HO- | CC(=O)O | 125 | null | CCOC(=O)C1C(=O)CCN(N2CCCCC2)C1=O>CC(=O)O>O=C1CCN(N2CCCCC2)C(=O)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b78fc203366846e59b80989b96967b76 | CC(=O)CNc1ccc(Cl)cc1Cl.O=C1CCN(N2CCCCC2)C(=O)C1>>Cc1cn(-c2ccc(Cl)cc2Cl)c2c1C(=O)N(N1CCCCC1)CC2 | C1(=CC=C(C=C1)S(=O)(=O)O)C.C1(=CC=C(C=C1)S(=O)(=O)O)C.N1(C(CC(CC1)=O)=O)N1CCCCC1.ClC1=C(C=CC(=C1)Cl)NCC(=O)C>>ClC1=C(C=CC(=C1)Cl)N1C=C(C=2C(N(CCC21)N2CCCCC2)=O)C | O=[C:2]([CH3:1])[CH2:3][NH:4][c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]1[Cl:12].O=[C:13]1[CH2:14][C:15](=[O:16])[N:17]([N:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:24][CH2:25]1>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][c:11]2[Cl:12])[c:13]2[c:14]1[C:15](=[O:16])[N:17]([N:18]1[CH2:19][... | CC(=O)CNc1ccc(Cl)cc1Cl.O=C1CCN(N2CCCCC2)C(=O)C1 | Cc1cn(-c2ccc(Cl)cc2Cl)c2c1C(=O)N(N1CCCCC1)CC2 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | c3eeaef71a5742d406a57fc1362a058d3239e8e2c1e614ea52e9a298a04273d2 | 4da15b4213f2884bf2fed954aed7c82e569801281a475847c3bea8d7588b2599 | O=C1c2ccn(-c3ccccc3)c2CCN1N1CCCCC1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[NH;D2;+0:4]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8](-[Cl;D1;H0:9]):[c:10].O=[C;H0;D3;+0:11]1-[C:12]-[C:13]-[#7:14](-[#7:15])-[C:16](=[O;D1;H0:17])-[CH2;D2;+0:18]-1>>[#7:15]-[#7:14]1-[C:13]-[C:12]-[c;H0;D3;+0:11]2:[c;H0;D3;+0:18](:[c;H0;D3;+0:1](-[C;D1;H3:2]):[cH;D2;+0:3]:[n;H0;D... | 43 | [{"value": 43.0, "product": "ClC1=C(C=CC(=C1)Cl)N1C=C(C=2C(N(CCC21)N2CCCCC2)=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1,1′-bipiperidine-2,4-dione (Example 15) (260 mg, 1.32 mmol) in dry toluene (25 mL) at rt were added 1-[(2,4-dichlorophenyl)amino]acetone (288 mg, 1.32 mmol, prepared in a similar manner to Example 25) followed by p-TSA (p-toluenesulfonic acid) (25 mg, 0.132 mmol). The mixture was heated at reflux with... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Secondary amine | null | C1CC[NH]CC1 | C1NCCc2[nH]ccc21 | c1ccccc1.C1NCCc2[nH]ccc21.C1CC[NH]CC1 | HO- | C1(=CC=CC=C1)C | null | null | CC(=O)CNc1ccc(Cl)cc1Cl.O=C1CCN(N2CCCCC2)C(=O)C1>C1(=CC=CC=C1)C>Cc1cn(-c2ccc(Cl)cc2Cl)c2c1C(=O)N(N1CCCCC1)CC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fc4081945ad94a06b2047b2452355331 | Cc1cn(-c2ccc(Cl)cc2Cl)c2c1C(=O)N(N1CCCCC1)CC2.O=C1CCC(=O)N1Br>>Cc1c2c(n(-c3ccc(Cl)cc3Cl)c1Br)CCN(N1CCCCC1)C2=O | O.ClC1=C(C=CC(=C1)Cl)N1C=C(C=2C(N(CCC21)N2CCCCC2)=O)C.BrN1C(CCC1=O)=O>>BrC1=C(C=2C(N(CCC2N1C1=C(C=C(C=C1)Cl)Cl)N1CCCCC1)=O)C | [CH3:1][c:2]1[c:3]2[c:4]([n:5](-[c:6]3[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]3[Cl:13])[cH:14]1)[CH2:16][CH2:17][N:18]([N:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)[C:25]2=[O:26].O=C1CCC(=O)N1[Br:15]>>[CH3:1][c:2]1[c:3]2[c:4]([n:5](-[c:6]3[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]3[Cl:13])[c:14]1[Br:15])[CH2:16][CH2:17... | Cc1cn(-c2ccc(Cl)cc2Cl)c2c1C(=O)N(N1CCCCC1)CC2.O=C1CCC(=O)N1Br | Cc1c2c(n(-c3ccc(Cl)cc3Cl)c1Br)CCN(N1CCCCC1)C2=O | null | null | CN(C)C=O | Functional Group Interconversion | Bromination | 0d9e251feb1fbae287306eec2368c8454cdb94b72683e437e8d7c15e30126037 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=C1c2ccn(-c3ccccc3)c2CCN1N1CCCCC1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:6]:[#7;a:7](-[c:8]):[cH;D2;+0:9]:[c:10]:1-[C;D1;H3:11]>>[#7:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[c:6]:[#7;a:7](-[c:8]):[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[c:10]:1-[C;D1;H3:11] | 75 | [{"value": 75.0, "product": "BrC1=C(C=2C(N(CCC2N1C1=C(C=C(C=C1)Cl)Cl)N1CCCCC1)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.4, "product": "BrC1=C(C=2C(N(CCC2N1C1=C(C=C(C=C1)Cl)Cl)N1CCCCC1)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a solution of 1-(2,4-dichlorophenyl)-3-methyl-5-(1-piperidinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (200 mg, 0.529 mmol, Example 16) at 0° C. in dry DMF was added NBS (N-bromosuccinimide) (99 mg, 0.555 mmol). The reaction mixture was stirred 1 h at 0° C., and then water was added. The resulting solutio... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | C1NCCc2[nH]ccc21.C1CCNC1 | C1NCCc2[nH]ccc21 | c1ccccc1.C1NCCc2[nH]ccc21.C1CC[NH]CC1 | HO- | CN(C)C=O | 0 | 1 | Cc1cn(-c2ccc(Cl)cc2Cl)c2c1C(=O)N(N1CCCCC1)CC2.O=C1CCC(=O)N1Br>CN(C)C=O>Cc1c2c(n(-c3ccc(Cl)cc3Cl)c1Br)CCN(N1CCCCC1)C2=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9d88810ec3fa46f2b9843685a10f101f | COc1ccc(-c2c(C)c3c(n2-c2ccccc2Cl)CCN([C@H]2CCCC[C@@H]2OCc2ccccc2)C3=O)cc1>>COc1ccc(-c2c(C)c3c(n2-c2ccccc2Cl)CCN([C@H]2CCCC[C@@H]2O)C3=O)cc1 | C(C1=CC=CC=C1)O[C@@H]1[C@H](CCCC1)N1C(C2=C(CC1)N(C(=C2C)C2=CC=C(C=C2)OC)C2=C(C=CC=C2)Cl)=O.C(C1=CC=CC=C1)O[C@@H]1[C@H](CCCC1)N.C(C1=CC=CC=C1)O[C@@H]1[C@H](CCCC1)N1C(C2=C(CC1)N(C(=C2C)C2=CC=C(C=C2)OC)C2=C(C=CC=C2)Cl)=O.C[Si](C)(C)I.ClC1=C(C=CC=C1)N1C(=CC=2CNCCC21)C2=CC=C(C=C2)OC>>ClC1=C(C=CC=C1)N1C(=C(C=2C(N(CCC21)[C@@H... | c1ccc(C[O:29][C@@H:28]2[C@@H:23]([N:22]3[CH2:21][CH2:20][c:11]4[c:10]([c:8]([CH3:9])[c:7](-[c:6]5[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:33][cH:32]5)[n:12]4-[c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[Cl:19])[C:30]3=[O:31])[CH2:24][CH2:25][CH2:26][CH2:27]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[c:8]([CH3:9])[c:10]3... | COc1ccc(-c2c(C)c3c(n2-c2ccccc2Cl)CCN([C@H]2CCCC[C@@H]2OCc2ccccc2)C3=O)cc1 | COc1ccc(-c2c(C)c3c(n2-c2ccccc2Cl)CCN([C@H]2CCCC[C@@H]2O)C3=O)cc1 | null | null | C(Cl)Cl | Deprotection | Hydroxyl benzyl deprotection | 655dc7217e93a347240a9b37b98ac62a0e37873ad7f15572a101946745db77a8 | 32e9a9ca3191eb6608eee26da72fef0d2c2afd087eefdbcc65ce4c46772064f8 | O=C1c2cc(-c3ccccc3)n(-c3ccccc3)c2CCN1C1CCCCC1 | [C:1]-[C:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1)-[C:4]>>[C:1]-[C:2](-[OH;D1;+0:3])-[C:4] | 24 | [{"value": 24.0, "product": "ClC1=C(C=CC=C1)N1C(=C(C=2C(N(CCC21)[C@@H]2[C@H](CCCC2)O)=O)C)C2=CC=C(C=C2)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | The starting material for this example, namely 5-[(1S,2S)-2-(benzyloxy)cyclohexyl]-1-(2-chlorophenyl)-2-(4-methoxyphenyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one, was prepared by following the methods described in Scheme 2 and Examples 12–19, using (1S,2S)-2-(benzyloxy)cyclohexylamine as R4NH2 (Schem... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1.C1NCCc2[nH]ccc21.C1CCCCC1 | Other | C(Cl)Cl | null | 18 | COc1ccc(-c2c(C)c3c(n2-c2ccccc2Cl)CCN([C@H]2CCCC[C@@H]2OCc2ccccc2)C3=O)cc1>C(Cl)Cl>COc1ccc(-c2c(C)c3c(n2-c2ccccc2Cl)CCN([C@H]2CCCC[C@@H]2O)C3=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2ffbd025e5a443f88cec01ba25c5378e | COc1ccc(CN2CCc3c(c(C)c(-c4ccc(Cl)cc4)n3-c3ccc(Cl)cc3Cl)C2=O)c(OC)c1>>Cc1c2c(n(-c3ccc(Cl)cc3Cl)c1-c1ccc(Cl)cc1)CCNC2=O | ClC1=CC=C(C=C1)C1=C(C=2C(N(CCC2N1C1=C(C=C(C=C1)Cl)Cl)CC1=C(C=C(C=C1)OC)OC)=O)C>>ClC1=CC=C(C=C1)C1=C(C=2C(NCCC2N1C1=C(C=C(C=C1)Cl)Cl)=O)C | COc1ccc(C[N:24]2[CH2:23][CH2:22][c:4]3[c:3]([c:2]([CH3:1])[c:14](-[c:15]4[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]4)[n:5]3-[c:6]3[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]3[Cl:13])[C:25]2=[O:26])c(OC)c1>>[CH3:1][c:2]1[c:3]2[c:4]([n:5](-[c:6]3[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]3[Cl:13])[c:14]1-[c:15]1[cH:16][cH:17][c... | COc1ccc(CN2CCc3c(c(C)c(-c4ccc(Cl)cc4)n3-c3ccc(Cl)cc3Cl)C2=O)c(OC)c1 | Cc1c2c(n(-c3ccc(Cl)cc3Cl)c1-c1ccc(Cl)cc1)CCNC2=O | null | null | FC(C(=O)O)(F)F | Reduction | Hydrogenolysis of tertiary amines | 83a899b8b971c7ca34e32d1ca65fd04f5e162ee243eccab6230c9b26771e4370 | 3efc6c7204ad36a2aa7236338bd7163bfb62d1e33efaad6b000b17910587541b | O=C1NCCc2c1cc(-c1ccccc1)n2-c1ccccc1 | C-O-c1:c:c:c(-C-[N;H0;D3;+0:1]2-[C:2]-[C:3]-[c:4](:[#7;a:5]):[c:6]-[C:7]-2=[O;D1;H0:8]):c(-O-C):c:1>>[#7;a:5]:[c:4]1:[c:6]-[C:7](=[O;D1;H0:8])-[NH;D2;+0:1]-[C:2]-[C:3]-1 | 73 | [{"value": 73.0, "product": "ClC1=CC=C(C=C1)C1=C(C=2C(NCCC2N1C1=C(C=C(C=C1)Cl)Cl)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.9, "product": "ClC1=CC=C(C=C1)C1=C(C=2C(NCCC2N1C1=C(C=C(C=C1)Cl)Cl)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-5-(2,4-dimethoxybenzyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (1.13 g, 2.03 mmol, Table 2, entry 176) in trifluoroacetic acid (40 mL) was heated at reflux temperature for 2 h. Trifluoroacetic acid was removed by evaporation under reduced press... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Tertiary amide | Secondary amide | c1ccccc1.C1NCCc2nccc21 | C1NCCc2[nH]ccc21 | c1ccccc1.c1ccccc1.C1NCCc2[nH]ccc21 | HO- | FC(C(=O)O)(F)F | null | null | COc1ccc(CN2CCc3c(c(C)c(-c4ccc(Cl)cc4)n3-c3ccc(Cl)cc3Cl)C2=O)c(OC)c1>FC(C(=O)O)(F)F>Cc1c2c(n(-c3ccc(Cl)cc3Cl)c1-c1ccc(Cl)cc1)CCNC2=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5ee44bbe9ff84184b47548d3f878aee1 | CC(=O)CI.Nc1ccccc1Cl>>CC(=O)CNc1ccccc1Cl | ClC1=C(N)C=CC=C1.ICC(C)=O.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>>ClC1=C(C=CC=C1)NCC(=O)C | I[CH2:4][C:2]([CH3:1])=[O:3].[NH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[Cl:12]>>[CH3:1][C:2](=[O:3])[CH2:4][NH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[Cl:12] | CC(=O)CI.Nc1ccccc1Cl | CC(=O)CNc1ccccc1Cl | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | c176e63a024701466caae2c04d3f5d2104f6d3bb155f520591ae3ee416bc3e3e | aa31def40a661a269b8a0fab7756768062834fd7bfb5c5af11ba9793df9868ba | c1ccccc1 | I-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:3]-[C:2](=[O;D1;H0:4])-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | 90.1 | [{"value": 77.0, "product": "ClC1=C(C=CC=C1)NCC(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.1, "product": "ClC1=C(C=CC=C1)NCC(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of chloroacetone (8.0 mL, 0.100 mol) in 100 mL acetone was added KI (33.20 g, 0.200 mol). The suspension was stirred under argon at rt for 24 h. Acetone was evaporated under reduced pressure. The residue was extracted with ether. The ethereal solution was concentrated under reduced pressure to yield iodoa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | Ketone.Secondary amine | null | null | c1ccccc1 | HI | O | null | null | CC(=O)CI.Nc1ccccc1Cl>O>CC(=O)CNc1ccccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-25102b621b5e4d25a5e2652806a36518 | NO.O=Cc1ccn(-c2ccccc2O)c1>>N#Cc1ccn(-c2ccccc2O)c1 | C(=O)C1=CN(C=C1)C1=C(C=CC=C1)O.C(C)N(CC)CC.Cl.NO>>C(#N)C1=CN(C=C1)C1=C(C=CC=C1)O | O[NH2:1].O=[CH:2][c:3]1[cH:4][cH:5][n:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[OH:13])[cH:14]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][n:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[OH:13])[cH:14]1 | NO.O=Cc1ccn(-c2ccccc2O)c1 | N#Cc1ccn(-c2ccccc2O)c1 | null | null | C(C)(=O)OC(C)=O | Miscellaneous | OtherReaction | 748a00525e7f639e600a6b1229bb8ce947b6e2e96d815c0b05b54470e6cdbc2a | a27285857ea2428fb666a281ae1a2b961eec077cb33a106e48534c99bfe3d865 | c1ccc(-n2cccc2)cc1 | O-[NH2;D1;+0:1].O=[CH;D2;+0:2]-[c:3]1:[c:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1>>[N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3]1:[c:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1 | 92 | [{"value": 92.0, "product": "C(#N)C1=CN(C=C1)C1=C(C=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.4, "product": "C(#N)C1=CN(C=C1)C1=C(C=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 2-(3-Formyl-1-pyrrolyl)phenol (3 g, 16 mmol) and triethylamine (17.6 mmol) are added to a suspension of hydroxylamine hydrochloride (1.22 g, 17.6 mmol) in acetic anhydride (7.7 ml), and the mixture is allowed to stir overnight at ambient temperature. The mixture is refluxed for 5 hours, concentrated, dissolved in 50 ml... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Nitrile | null | null | c1cc[nH]c1.c1ccccc1 | HO- | C(C)(=O)OC(C)=O | null | 8 | NO.O=Cc1ccn(-c2ccccc2O)c1>C(C)(=O)OC(C)=O>N#Cc1ccn(-c2ccccc2O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0cf57611eb694aa89dccdcbfac107543 | COc1ccccc1B(O)O.N#Cc1ccc(Br)s1>>COc1ccccc1-c1ccc(C#N)s1 | ClCCl.BrC1=CC=C(S1)C#N.COC1=C(C=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>C(#N)C1=CC=C(S1)C1=C(C=CC=C1)OC | OB(O)[c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1.Br[c:9]1[cH:10][cH:11][c:12]([C:13]#[N:14])[s:15]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][cH:11][c:12]([C:13]#[N:14])[s:15]1 | COc1ccccc1B(O)O.N#Cc1ccc(Br)s1 | COc1ccccc1-c1ccc(C#N)s1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1.O | C-C Coupling | Suzuki coupling with boronic acids | a9e750b5cb26673fc488a731642519fa5963d6a2e4d2eeb976470c7f17606def | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccs2)cc1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1.O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[#8:10]):[c:11]>>[#8:10]-[c:9](:[c:11]):[c;H0;D3;+0:6](-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[c:5]:1):[c:7]:[c:8] | 96 | [{"value": 96.0, "product": "C(#N)C1=CC=C(S1)C1=C(C=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.7, "product": "C(#N)C1=CC=C(S1)C1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | A solution of 5-bromothiophene-2-carbonitrile (1.25 g, 6.65 mmol) in 50 ml of dioxane is degassed with argon, tetrakis(triphenylphosphine)palladium(0) (768 mg, 0.665 mmol) is added and the mixture is stirred for 5 minutes. 2-Methoxybenzene boronic acid (2.02 g, 13.3 mmol) and aqueous 2 N sodium carbonate (13.3 ml) are ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | c1ccccc1.c1ccsc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.O | null | 0.083333 | COc1ccccc1B(O)O.N#Cc1ccc(Br)s1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1.O>COc1ccccc1-c1ccc(C#N)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-03251ddc1f3e4d94aef166f6ac65dfbe | C=CC(C)=O.Nc1ccccn1.O=C1NC(=O)c2ccccc21>>O=C1c2ccccc2C(=O)N1CCc1cn2ccccc2n1 | C=CC(C)=O.C1(C=2C(C(N1)=O)=CC=CC2)=O.BrCC(CCN1C(C2=CC=CC=C2C1=O)=O)=O.NC1=NC=CC=C1>>BrCC(CCN1C(C2=CC=CC=C2C1=O)=O)=O.N=1C(=CN2C1C=CC=C2)CCN2C(C1=CC=CC=C1C2=O)=O | O=[C:31]([CH:30]=[CH2:29])[CH3:32].[n:33]1[cH:34][cH:35][cH:36][cH:37][c:38]1[NH2:39].[O:18]=[C:19]1[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26](=[O:27])[NH:28]1>>[O:18]=[C:19]1[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26](=[O:27])[N:28]1[CH2:29][CH2:30][c:31]1[cH:32][n:33]2[cH:34][cH:35][cH:36][cH:37][c:38]2[n:... | C=CC(C)=O.Nc1ccccn1.O=C1NC(=O)c2ccccc21 | O=C1c2ccccc2C(=O)N1CCc1cn2ccccc2n1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | fe19272faa31f0cb9f07f60ebae4a5d6da5396213b603a1c83271580797fbf6e | bad28b42d078f16f7e7f6d5fbd1d95e2bb8a5073fbdb3d319b6480dc943a901f | O=C1c2ccccc2C(=O)N1CCc1cn2ccccc2n1 | O=[C;H0;D3;+0:1](-[CH3;D1;+0:2])-[CH;D2;+0:3]=[CH2;D1;+0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[n;H0;D2;+0:8]:[c:9]:[c:10].[O;D1;H0:11]=[C:12]1-[NH;D2;+0:13]-[C:14](=[O;D1;H0:15])-[c:16]:[c:17]-1>>[O;D1;H0:11]=[C:12]1-[c:17]:[c:16]-[C:14](=[O;D1;H0:15])-[N;H0;D3;+0:13]-1-[CH2;D2;+0:4]-[CH2;D2;+0:3]-[c;H0;D3;+0:1]1:[cH;D2;+0:2... | 96.6 | [{"value": 49.0, "product": "N=1C(=CN2C1C=CC=C2)CCN2C(C1=CC=CC=C1C2=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.6, "product": "N=1C(=CN2C1C=CC=C2)CCN2C(C1=CC=CC=C1C2=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-(4-Bromo-3-oxo-butyl)-isoindole-1,3-dione is prepared by condensation of but-1-en-3-one with phthalimide followed by bromination according to known procedures (J. Med. Chem., 35:3239, 1992. A solution of 2-(4-bromo-3-oxo-butyl)-isoindole-1,3-dione (8.9 g, 30.06 mmol) and 2-aminopyridine (2.8 g, 29.75 mmol) in ethanol... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Unsubstituted dicarboximide.Primary amine.Vinyl | Substituted dicarboximide | c1ccncc1.c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2.c1ccn2ccnc2c1 | c1ccc2c(c1)C[NH]C2.c1ccn2ccnc2c1 | HO- | C(C)O | null | null | C=CC(C)=O.Nc1ccccn1.O=C1NC(=O)c2ccccc21>C(C)O>O=C1c2ccccc2C(=O)N1CCc1cn2ccccc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-37ed76e448754df0a9ef4d3a2cb23443 | CC(C)(N)CC(=O)O.O=C1OC(=O)c2ccccc21>>CC(C)(CC(=O)O)N1C(=O)c2ccccc2C1=O | NC(CC(=O)O)(C)C.C1(C=2C(C(=O)O1)=CC=CC2)=O>>CC(CC(=O)O)(N1C(C2=CC=CC=C2C1=O)=O)C | [CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[OH:7])[NH2:8].O1[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[C:17]1=[O:18]>>[CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[OH:7])[N:8]1[C:9](=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[C:17]1=[O:18] | CC(C)(N)CC(=O)O.O=C1OC(=O)c2ccccc21 | CC(C)(CC(=O)O)N1C(=O)c2ccccc2C1=O | null | null | C(C)O | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1NC(=O)c2ccccc21 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[NH2;D1;+0:4])-[C:5]-[C:6](=[O;D1;H0:7])-[O;D1;H1:8].[O;D1;H0:9]=[C;H0;D3;+0:10]1-O-[C;H0;D3;+0:11](=[O;D1;H0:12])-[c:13](:[c:14]):[c:15]-1:[c:16]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C:5]-[C:6](=[O;D1;H0:7])-[O;D1;H1:8])-[N;H0;D3;+0:4]1-[C;H0;D3;+0:11](=[O;D1;H0:12])-[c:13](:[c:14]):[c:1... | 58 | [{"value": 58.0, "product": "CC(CC(=O)O)(N1C(C2=CC=CC=C2C1=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.2, "product": "CC(CC(=O)O)(N1C(C2=CC=CC=C2C1=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | 54 | HOUR | An intimate mixture of of 3-amino-3-methyl butanoic acid (27.4 g, 0.234 mol) and phthalic anhydride (38.1 g, 0.257 mol) is heated at 180° C. for 1.5 hours. After cooling, the reaction mixture is dissolved in 40 ml of ethanol and kept in a refrigerator for 54 hours. The colorless crystalline precipitate thus obtained is... | 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 | HO- | C(C)O | 180 | 54 | CC(C)(N)CC(=O)O.O=C1OC(=O)c2ccccc21>C(C)O>CC(C)(CC(=O)O)N1C(=O)c2ccccc2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b797af70be854695acaa06e83a90aaeb | CC(C)(CC(=O)O)N1C(=O)c2ccccc2C1=O.NCc1ccccn1>>CC(C)(CC(=O)NCc1ccccn1)N1C(=O)c2ccccc2C1=O | CC(CC(=O)O)(N1C(C2=CC=CC=C2C1=O)=O)C.NCC1=NC=CC=C1>>N1=C(C=CC=C1)CNC(CC(N1C(C2=CC=CC=C2C1=O)=O)(C)C)=O | O[C:5]([CH2:4][C:2]([CH3:1])([CH3:3])[N:15]1[C:16](=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[C:24]1=[O:25])=[O:6].[NH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1>>[CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[NH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][n:14]1)[N:15]1[C:16](=[O:17])[c:18]2[cH:19][cH:20]... | CC(C)(CC(=O)O)N1C(=O)c2ccccc2C1=O.NCc1ccccn1 | CC(C)(CC(=O)NCc1ccccn1)N1C(=O)c2ccccc2C1=O | null | null | C(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CCN1C(=O)c2ccccc2C1=O)NCc1ccccn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]:[c:6]-[C:7]-[NH2;D1;+0:8]>>[#7;a:5]:[c:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | 58.3 | [{"value": 58.0, "product": "N1=C(C=CC=C1)CNC(CC(N1C(C2=CC=CC=C2C1=O)=O)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.3, "product": "N1=C(C=CC=C1)CNC(CC(N1C(C2=CC=CC=C2C1=O)=O)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of β,β-dimethyl-1,3-dioxo-2-isoindolinepropionic acid (5 g, 20.2 mmol) and N,N-dicyclohexylcarbodiimide (4.6 g, 22.24 mmol) in 50 ml of dry methylene chloride is added 2-(aminomethyl)pyridine (2.41 g, 2.3 ml, 22.24 mmol) at ambient temperature. The mixture is stirred for 24 hours. The precipitate of dicyc... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccc2c(c1)C[NH]C2 | HO- | C(Cl)Cl | null | 24 | CC(C)(CC(=O)O)N1C(=O)c2ccccc2C1=O.NCc1ccccn1>C(Cl)Cl>CC(C)(CC(=O)NCc1ccccn1)N1C(=O)c2ccccc2C1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-735b516f55264b85ba2e9e18846ec391 | C=[N+](C)C.[I-].c1cnc2[nH]ccc2c1>>CN(C)Cc1c[nH]c2ncccc12.I | N1C=CC2=CC=CN=C12.C[N+](=C)C.[I-]>>I.CN(C)CC1=CNC2=NC=CC=C12 | [CH3:1][N+:2]([CH3:3])=[CH2:4].[I-:14].[cH:5]1[cH:6][nH:7][c:8]2[n:9][cH:10][cH:11][cH:12][c:13]12>>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][nH:7][c:8]2[n:9][cH:10][cH:11][cH:12][c:13]12.[IH:14] | C=[N+](C)C.[I-].c1cnc2[nH]ccc2c1 | CN(C)Cc1c[nH]c2ncccc12.I | null | null | C(C)(=O)O | C-C Coupling | OtherReaction | 056025bccbd355e6a7ea9f01f673db1cd68dd717ff514abfa298d9bfd557edfe | 5c03404e5740858973798689d4be0a8ed62608f5043e578ba3cd6de4363e2dbe | c1cnc2[nH]ccc2c1 | [C;D1;H3:1]-[N+;H0;D3:2](-[C;D1;H3:3])=[CH2;D1;+0:4].[I-;H0;D0:5].[c:6]:[#7;a:7]:[c:8]1:[#7;a:9]:[c:10]:[cH;D2;+0:11]:[c:12]:1:[c:13]>>[C;D1;H3:1]-[N;H0;D3;+0:2](-[C;D1;H3:3])-[CH2;D2;+0:4]-[c;H0;D3;+0:11]1:[c:10]:[#7;a:9]:[c:8](:[#7;a:7]:[c:6]):[c:12]:1:[c:13].[IH;D0;+0:5] | null | [] | 65 | CELSIUS | null | null | 7-Azaindole (5.05 g, 43 mmol) and Eschenmoser's salt (N,N-dimethylmethyleneammonium iodide; 8.48 g, 45 mmol) are combined in 100 ml of glacial acetic acid. After heating at 65° C. for 1 hour, the reaction mixture is concentrated in vacuo. The resulting solid is triturated with ethyl acetate, filtered and dried in vacuo... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | c1cnc2[nH]ccc2c1 | null | C(C)(=O)O | 65 | null | C=[N+](C)C.[I-].c1cnc2[nH]ccc2c1>C(C)(=O)O>CN(C)Cc1c[nH]c2ncccc12.I |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eea38e3147f941809ffb13454bc8a7c8 | CC(C)[N+](=O)[O-].CN(C)Cc1c[nH]c2ncccc12>>CC(C)(Cc1c[nH]c2ncccc12)[N+](=O)[O-] | I.CN(C)CC1=CNC2=NC=CC=C12.CI.C[O-].[Na+].[N+](=O)([O-])C(C)C>>CC(CC1=CNC2=NC=CC=C12)(C)[N+](=O)[O-] | [CH3:1][CH:2]([CH3:3])[N+:14](=[O:15])[O-:16].CN(C)[CH2:4][c:5]1[cH:6][nH:7][c:8]2[n:9][cH:10][cH:11][cH:12][c:13]12>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][nH:7][c:8]2[n:9][cH:10][cH:11][cH:12][c:13]12)[N+:14](=[O:15])[O-:16] | CC(C)[N+](=O)[O-].CN(C)Cc1c[nH]c2ncccc12 | CC(C)(Cc1c[nH]c2ncccc12)[N+](=O)[O-] | null | null | [NH4+].[Cl-].CO.C(C)(=O)OCC | C-C Coupling | OtherReaction | 410d0ecf550dfec32b5bd37f61aeafc75533d5e4329aa3110c08acb15e21dcaa | fc73a0ba4f6f90cb21df47612bcde105fcd2a049cd56b52924f944fc6a6cbe55 | c1cnc2[nH]ccc2c1 | C-N(-C)-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4](:[#7;a:5]):[#7;a:6]:[c:7]:1.[C;D1;H3:8]-[CH;D3;+0:9](-[C;D1;H3:10])-[#7;+:11](-[O;-;D1;H0:12])=[O;D1;H0:13]>>[#7;a:5]:[c:4]1:[#7;a:6]:[c:7]:[c:2](-[CH2;D2;+0:1]-[C;H0;D4;+0:9](-[C;D1;H3:8])(-[C;D1;H3:10])-[#7;+:11](-[O;-;D1;H0:12])=[O;D1;H0:13]):[c:3]:1 | 92 | [{"value": 92.0, "product": "CC(CC1=CNC2=NC=CC=C12)(C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A 0° C. solution of 3-dimethylaminomethyl-1H-7-azaindole hydroiodide (10 g, 33 mmol) in 46 ml of methanol and 46 ml of 2-nitropropane is treated with methyl iodide (2.15 ml, 35 mmol) and solid sodium methoxide (3.65 g, 68 mmol) sequentially. The resulting mixture is allowed to warm to ambient temperature, and, after st... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Tertiary amine | Nitro group | null | null | c1cnc2[nH]ccc2c1 | Other | [NH4+].[Cl-].CO.C(C)(=O)OCC | null | 8 | CC(C)[N+](=O)[O-].CN(C)Cc1c[nH]c2ncccc12>[NH4+].[Cl-].CO.C(C)(=O)OCC>CC(C)(Cc1c[nH]c2ncccc12)[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bcd96f282a0b42aebd3d55cb6b3b5052 | BrBr.C=CC=O.CC(C)[N+](=O)[O-]>>CC(C)(CC(Br)C=O)[N+](=O)[O-] | C(=O)C=C.[N+](=O)([O-])C(C)C.CC(CCC=O)(C)[N+](=O)[O-].BrBr>>CC(CCC=O)(C)[N+](=O)[O-].BrC(C=O)CC(C)([N+](=O)[O-])C | Br[Br:6].[CH2:1]=[CH:5][CH:7]=[O:8].[CH:2]([CH3:3])([CH3:4])[N+:9](=[O:10])[O-:11]>>[CH3:1][C:2]([CH3:3])([CH2:4][CH:5]([Br:6])[CH:7]=[O:8])[N+:9](=[O:10])[O-:11] | BrBr.C=CC=O.CC(C)[N+](=O)[O-] | CC(C)(CC(Br)C=O)[N+](=O)[O-] | null | null | O.C(C)(=O)O | C-C Coupling | OtherReaction | bd3ac79662011be9149b4c953fba45a902bf7153fc7cbf85f8297521df255f54 | 2d5d05895dd6418ad448d0782a091325da1d87ac6d371c11269c83d301868b70 | null | Br-[Br;H0;D1;+0:1].[C;D1;H3:2]-[CH;D3;+0:3](-[CH3;D1;+0:4])-[#7;+:5](-[O;-;D1;H0:6])=[O;D1;H0:7].[CH2;D1;+0:8]=[CH;D2;+0:9]-[C:10]=[O;D1;H0:11]>>[Br;H0;D1;+0:1]-[CH;D3;+0:9](-[C:10]=[O;D1;H0:11])-[CH2;D2;+0:4]-[C;H0;D4;+0:3](-[C;D1;H3:2])(-[CH3;D1;+0:8])-[#7;+:5](-[O;-;D1;H0:6])=[O;D1;H0:7] | 163.1 | [{"value": 163.1, "product": "BrC(C=O)CC(C)([N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | 4-Methyl-4-nitropentanal is prepared by condensation of acrolein and 2-nitropropane according to a known procedure (Synthesis 1986, 237). To a solution of 4-methyl-4-nitropentanal (8.5 g, 58.56 mmol) in acetic acid (125 ml) is added bromine (9.12 g, 57.07 mmol) dropwise while the temperature is kept below 15° C. After ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group.Vinyl | Secondary halide.Aldehyde.Nitro group | null | null | null | HBr | O.C(C)(=O)O | null | 0.25 | BrBr.C=CC=O.CC(C)[N+](=O)[O-]>O.C(C)(=O)O>CC(C)(CC(Br)C=O)[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8f7b661a8c334a4c812e0988775af118 | CC(C)(CC(Br)C=O)[N+](=O)[O-].Nc1ncccc1OCc1ccccc1>>CC(C)(Cc1cnc2c(OCc3ccccc3)cccn12)[N+](=O)[O-] | NC1=NC=CC=C1OCC1=CC=CC=C1.BrC(C=O)CC(C)([N+](=O)[O-])C>>CC(CC1=CN=C2N1C=CC=C2OCC2=CC=CC=C2)(C)[N+](=O)[O-] | O=[CH:6][CH:5](Br)[CH2:4][C:2]([CH3:1])([CH3:3])[N+:22](=[O:23])[O-:24].[NH2:7][c:8]1[c:9]([O:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][cH:19][cH:20][n:21]1>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][n:7][c:8]2[c:9]([O:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19][cH:20][n:2... | CC(C)(CC(Br)C=O)[N+](=O)[O-].Nc1ncccc1OCc1ccccc1 | CC(C)(Cc1cnc2c(OCc3ccccc3)cccn12)[N+](=O)[O-] | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 3a7835efa5ac56b87be43234b54606ae621fc957a5ff407573e590f6174c2545 | 4efe5597cd78b75eedda88a299158b349ae1f03c7cd5a6a1daf8cec0515aae7c | c1ccc(COc2cccn3ccnc23)cc1 | Br-[CH;D3;+0:1](-[C:2]-[C:3])-[CH;D2;+0:4]=O.[NH2;D1;+0:5]-[c:6](:[c:7]):[n;H0;D2;+0:8]:[c:9]:[c:10]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:4]:[n;H0;D2;+0:5]:[c:6](:[c:7]):[n;H0;D3;+0:8]:1:[c:9]:[c:10] | 64.4 | [{"value": 64.0, "product": "CC(CC1=CN=C2N1C=CC=C2OCC2=CC=CC=C2)(C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.4, "product": "CC(CC1=CN=C2N1C=CC=C2OCC2=CC=CC=C2)(C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 2-amino-3-benzyloxypyridine (2.7 g, 13.5 mmol) and 2-bromo-4-methyl-4-nitropentanal (3.0 g, 13.5 mmol) in ethanol (20 ml) is heated at 100° C. overnight. The solvent is removed under reduced pressure and the residue is treated with saturated aqueous NaHCO3 solution. The aqueous mixture is extracted two tim... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | HBr | C(C)O | 100 | null | CC(C)(CC(Br)C=O)[N+](=O)[O-].Nc1ncccc1OCc1ccccc1>C(C)O>CC(C)(Cc1cnc2c(OCc3ccccc3)cccn12)[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6acc8a33ef804c1a86c2573a8963d318 | CC(C)(Cc1cnc2cc(O)ccn12)[N+](=O)[O-].NC(=O)CCl>>CC(C)(Cc1cnc2cc(OCC(N)=O)ccn12)[N+](=O)[O-] | CC(CC1=CN=C2N1C=CC(=C2)O)(C)[N+](=O)[O-].ClCC(=O)N.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>>CC(CC1=CN=C2N1C=CC(=C2)OCC(=O)N)(C)[N+](=O)[O-] | [CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][n:7][c:8]2[cH:9][c:10]([OH:11])[cH:16][cH:17][n:18]12)[N+:19](=[O:20])[O-:21].Cl[CH2:12][C:13]([NH2:14])=[O:15]>>[CH3:1][C:2]([CH3:3])([CH2:4][c:5]1[cH:6][n:7][c:8]2[cH:9][c:10]([O:11][CH2:12][C:13]([NH2:14])=[O:15])[cH:16][cH:17][n:18]12)[N+:19](=[O:20])[O-:21] | CC(C)(Cc1cnc2cc(O)ccn12)[N+](=O)[O-].NC(=O)CCl | CC(C)(Cc1cnc2cc(OCC(N)=O)ccn12)[N+](=O)[O-] | null | null | CC(CC)=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccn2ccnc2c1 | Cl-[CH2;D2;+0:1]-[C:2](-[N;D1;H2:3])=[O;D1;H0:4].[#7;a:5]:[c:6]1:[#7;a:7]:[c:8]:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]:1>>[#7;a:5]:[c:6]1:[#7;a:7]:[c:8]:[c:9]:[c:10](-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[C:2](-[N;D1;H2:3])=[O;D1;H0:4]):[c:12]:1 | 34.3 | [{"value": 34.0, "product": "CC(CC1=CN=C2N1C=CC(=C2)OCC(=O)N)(C)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.3, "product": "CC(CC1=CN=C2N1C=CC(=C2)OCC(=O)N)(C)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3-(2-Methyl-2-nitropropyl)imidazo[1,2-a]pyridin-7-ol (1.5 g, 6.38 mmol), chloroacetamide (1.19 g, 12.73 mmol), potassium carbonate (6.4 mmol) and a small amount of potassium iodide in 2-butanone (30 ml) is heated at reflux overnight. The solids are removed by filtration and the filtrate is concentrated under reduced pr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccn2ccnc2c1 | HCl | CC(CC)=O | null | null | CC(C)(Cc1cnc2cc(O)ccn12)[N+](=O)[O-].NC(=O)CCl>CC(CC)=O>CC(C)(Cc1cnc2cc(OCC(N)=O)ccn12)[N+](=O)[O-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a7d971e9763c4e23bba9f02f13b16231 | CC(C)(CC(Br)C=O)[N+](=O)[O-].Cc1ccnc(N)c1>>Cc1ccn2c(CC(C)(C)[N+](=O)[O-])cnc2c1 | NC1=NC=CC(=C1)C.BrC(C=O)CC(C)([N+](=O)[O-])C>>CC1=CC=2N(C=C1)C(=CN2)CC(C)([N+](=O)[O-])C | O=[CH:14][CH:6](Br)[CH2:7][C:8]([CH3:9])([CH3:10])[N+:11](=[O:12])[O-:13].[CH3:1][c:2]1[cH:3][cH:4][n:5][c:16]([NH2:15])[cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][n:5]2[c:6]([CH2:7][C:8]([CH3:9])([CH3:10])[N+:11](=[O:12])[O-:13])[cH:14][n:15][c:16]2[cH:17]1 | CC(C)(CC(Br)C=O)[N+](=O)[O-].Cc1ccnc(N)c1 | Cc1ccn2c(CC(C)(C)[N+](=O)[O-])cnc2c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3a7835efa5ac56b87be43234b54606ae621fc957a5ff407573e590f6174c2545 | 4efe5597cd78b75eedda88a299158b349ae1f03c7cd5a6a1daf8cec0515aae7c | c1ccn2ccnc2c1 | Br-[CH;D3;+0:1](-[C:2]-[C:3])-[CH;D2;+0:4]=O.[NH2;D1;+0:5]-[c:6](:[c:7]):[n;H0;D2;+0:8]:[c:9]:[c:10]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:4]:[n;H0;D2;+0:5]:[c:6](:[c:7]):[n;H0;D3;+0:8]:1:[c:9]:[c:10] | 63.4 | [{"value": 63.0, "product": "CC1=CC=2N(C=C1)C(=CN2)CC(C)([N+](=O)[O-])C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.4, "product": "CC1=CC=2N(C=C1)C(=CN2)CC(C)([N+](=O)[O-])C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Amino-4-methylpyridine (2.2 g, 20.3 mmol) and 2-bromo-4-methyl4-nitropentanal (20.3 mmol) are reacted as described in Amine 7 to give 3.0 g of 7-methyl-3-(2-methyl-2-nitropropyl)imidazo[1,2-a]pyridine (63%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Aldehyde.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1 | HBr | null | null | null | CC(C)(CC(Br)C=O)[N+](=O)[O-].Cc1ccnc(N)c1>>Cc1ccn2c(CC(C)(C)[N+](=O)[O-])cnc2c1 |
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