dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-524f8dc4a789487889bf25d15554823c | COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1)C3>>COc1ccc2[nH]c3cc(-c4cc([N+](=O)[O-])cc([N+](=O)[O-])c4)c4c(c3c2c1)C(=O)NC4=O | [N+](=O)([O-])C=1C=C(C=C(C1)[N+](=O)[O-])C1CC=2NC=3C=CC(=CC3C2C2C1C(NC2=O)=O)OC.C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N>>[N+](=O)([O-])C=1C=C(C=C(C1)[N+](=O)[O-])C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[c:25]([c:26]2[cH:27]1)[CH:24]1[CH:23]([CH:10]([c:11]2[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][c:18]([N+:19](=[O:20])[O-:21])[cH:22]2)[CH2:9]3)[C:31](=[O:32])[NH:30][C:28]1=[O:29]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[cH:9][c:10](-[c:11]4[cH:12][c:13]([N+... | COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1)C3 | COc1ccc2[nH]c3cc(-c4cc([N+](=O)[O-])cc([N+](=O)[O-])c4)c4c(c3c2c1)C(=O)NC4=O | null | null | null | Oxidation | OtherReaction | 3d157ee1e52021ba4f102c0e4bf23d31153db03cc8f65d6ae2d3bbc53db1b830 | 82a3692de44364afcfd8cc4460435180e0752c31812bf6008d75e02664a32947 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | [O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6]2-[CH;D3;+0:7](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12])-[CH2;D2;+0:13]-[c:14]3:[#7;a:15]:[c:16]:[c:17]:[c:18]:3-[CH;D3;+0:19]-1-2>>[O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[c;H0;D3;+0:6]2:[c;H0;D3;+0:7](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[cH... | 42 | [{"value": 42.0, "product": "[N+](=O)([O-])C=1C=C(C=C(C1)[N+](=O)[O-])C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 4-(3,5-Dinitrophenyl)-9-methoxy-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dione (IV; Ar=3,5-dinitrophenyl, R═H) (41) prepared as described in example 47 with DDQ according to the procedure described in example 70 gave 4-(3,5-dinitrophenyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c3c([nH]c2c1)CCC1CNCC31 | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | null | null | null | null | COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1)C3>>COc1ccc2[nH]c3cc(-c4cc([N+](=O)[O-])cc([N+](=O)[O-])c4)c4c(c3c2c1)C(=O)NC4=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9646ed85d1e945ff98b8b534569f0755 | COc1ccc2[nH]c3cc(-c4cc([N+](=O)[O-])cc([N+](=O)[O-])c4)c4c(c3c2c1)C(=O)NC4=O>>O=C1NC(=O)c2c1c(-c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1)cc1[nH]c3ccc(O)cc3c21 | [N+](=O)([O-])C=1C=C(C=C(C1)[N+](=O)[O-])C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC.Cl.[NH+]1=CC=CC=C1>>[N+](=O)([O-])C=1C=C(C=C(C1)[N+](=O)[O-])C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O | C[O:28][c:27]1[cH:26][cH:25][c:24]2[nH:23][c:22]3[cH:21][c:8](-[c:9]4[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20]4)[c:7]4[c:6]([c:31]3[c:30]2[cH:29]1)[C:4](=[O:5])[NH:3][C:2]4=[O:1]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:... | COc1ccc2[nH]c3cc(-c4cc([N+](=O)[O-])cc([N+](=O)[O-])c4)c4c(c3c2c1)C(=O)NC4=O | O=C1NC(=O)c2c1c(-c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1)cc1[nH]c3ccc(O)cc3c21 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 57 | [{"value": 57.0, "product": "[N+](=O)([O-])C=1C=C(C=C(C1)[N+](=O)[O-])C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 4-(3,5-dinitrophenyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=3,5-dinitrophenyl, R10═H) (42) prepared as described in example 48 with pyridinium hydrochloride according to the proceedure described in example 81 gave 4-(3,5-Dinitrophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | Other | null | null | null | COc1ccc2[nH]c3cc(-c4cc([N+](=O)[O-])cc([N+](=O)[O-])c4)c4c(c3c2c1)C(=O)NC4=O>>O=C1NC(=O)c2c1c(-c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1)cc1[nH]c3ccc(O)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-26238d58532742e1a9fd9a0ceaebf033 | COc1ccc2c(c1)cc(C=Cc1ccccc1OC)n2CCCO[Si](C)(C)C(C)(C)C.O=C1C=CC(=O)N1>>COc1ccc2c(c1)c1c(n2CCCO[Si](C)(C)C(C)(C)C)CC(c2ccccc2OC)C2C(=O)NC(=O)C12 | C1(C=CC(N1)=O)=O.[Si](C)(C)(C(C)(C)C)OCCCN1C(=CC2=CC(=CC=C12)OC)C=CC1=C(C=CC=C1)OC>>[Si](C)(C)(C(C)(C)C)OCCCN1C=2C=CC(=CC2C=2C3C(C(CC12)C1=C(C=CC=C1)OC)C(NC3=O)=O)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[cH:9][c:10]([CH:23]=[CH:24][c:25]1[cH:26][cH:27][cH:28][cH:29][c:30]1[O:31][CH3:32])[n:11]2[CH2:12][CH2:13][CH2:14][O:15][Si:16]([CH3:17])([CH3:18])[C:19]([CH3:20])([CH3:21])[CH3:22].[CH:33]1=[CH:39][C:37](=[O:38])[NH:36][C:34]1=[O:35]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c... | COc1ccc2c(c1)cc(C=Cc1ccccc1OC)n2CCCO[Si](C)(C)C(C)(C)C.O=C1C=CC(=O)N1 | COc1ccc2c(c1)c1c(n2CCCO[Si](C)(C)C(C)(C)C)CC(c2ccccc2OC)C2C(=O)NC(=O)C12 | null | null | null | C-C Coupling | OtherReaction | cb72f4a0e87703d4feb5445ea9e00fcafa1b033ce261ae8123af01ad6ee77064 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C1NC(=O)C2C(c3ccccc3)Cc3[nH]c4ccccc4c3C12 | [C:1]-[#7;a:2]1:[c:3](-[CH;D2;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[cH;D2;+0:9]:[c:10](:[c:11]):[c:12]:1:[c:13].[O;D1;H0:14]=[C:15]1-[#7:16]-[C:17](=[O;D1;H0:18])-[CH;D2;+0:19]=[CH;D2;+0:20]-1>>[C:1]-[#7;a:2]1:[c:3]2:[c;H0;D3;+0:9](:[c:10](:[c:11]):[c:12]:1:[c:13])-[CH;D3;+0:19]1-[C:17](=[O;D1;H0:18])-[#7:16]-[C:15]... | 89 | [{"value": 89.0, "product": "[Si](C)(C)(C(C)(C)C)OCCCN1C=2C=CC(=CC2C=2C3C(C(CC12)C1=C(C=CC=C1)OC)C(NC3=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 1-(3-{[tert-Butyl(dimethyl)silyl]oxy}propyl)-5-methoxy-2-[2-(2-methoxyphenyl)ethenyl]-1H-indole (III; Ar=2-methoxyphenyl, R10═CH2CH2CH2OSiMe2t-Bu) (98) prepared as described in example 51 with maleimide using the procedure described in example 68 gave 6-(3-{[tert-Butyl(dimethyl)silyl]oxy}propyl)-9-metho... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]ccc2c1.C1=CCNC1 | C1NCC2c3c([nH]c4ccccc34)C[CH]C12 | c1ccccc1.C1NCC2c3c([nH]c4ccccc34)C[CH]C12 | null | null | null | null | COc1ccc2c(c1)cc(C=Cc1ccccc1OC)n2CCCO[Si](C)(C)C(C)(C)C.O=C1C=CC(=O)N1>>COc1ccc2c(c1)c1c(n2CCCO[Si](C)(C)C(C)(C)C)CC(c2ccccc2OC)C2C(=O)NC(=O)C12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1860bb7aaf754f549fac96415c1c1103 | COc1ccc2c(c1)c1c(n2CCCO[Si](C)(C)C(C)(C)C)CC(c2ccccc2OC)C2C(=O)NC(=O)C12>>COc1ccc2c(c1)c1c3c(c(-c4ccccc4OC)cc1n2CCCO)C(=O)NC3=O | [Si](C)(C)(C(C)(C)C)OCCCN1C=2C=CC(=CC2C=2C3C(C(CC12)C1=C(C=CC=C1)OC)C(NC3=O)=O)OC.C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N.Cl>>OCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)OC)C(NC3=O)=O)OC | CC(C)(C)[Si](C)(C)[O:27][CH2:26][CH2:25][CH2:24][n:23]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]2[c:9]2[c:22]1[CH2:21][CH:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[O:19][CH3:20])[CH:11]1[CH:10]2[C:31](=[O:32])[NH:30][C:28]1=[O:29]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[c:9]1[c:10]3[c:11]([c:12]... | COc1ccc2c(c1)c1c(n2CCCO[Si](C)(C)C(C)(C)C)CC(c2ccccc2OC)C2C(=O)NC(=O)C12 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4OC)cc1n2CCCO)C(=O)NC3=O | null | null | C1CCOC1.CO | Miscellaneous | OtherReaction | 6c9712e00c7b4d1c5f8a072ac030d252cf1631f2fe61823cdac905a14569b28d | 8810278526f6a2c0e6c6bc11dce581d57652dfa7eee92b5b7a2e8cacd394ef1e | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]-[C:4]-[#7;a:5]1:[c:6]:[c:7]:[c:8]2:[c:9]:1-[CH2;D2;+0:10]-[CH;D3;+0:11](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15](-[#8:16]):[c:17])-[CH;D3;+0:18]1-[C:19](=[O;D1;H0:20])-[#7:21]-[C:22](=[O;D1;H0:23])-[CH;D3;+0:24]-1-2>>[#8:16]-[c:15](:[c:17]):[c;H0;D3;+0:12](-[c;H0;D3;+0... | 72 | [{"value": 72.0, "product": "OCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)OC)C(NC3=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 6-(3-{[tert-Butyl(dimethyl)silyl)oxy}propyl)-9-methoxy-4-(2-methoxyphenyl)-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dione (IV; Ar=2-methoxyphenyl; R10═CH2CH2CH2OSiMe2t-Bu) prepared as described in example 52 with DDQ using the procedure described in example 70 followed reaction with 2N HC... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | C1NCC2c3c([nH]c4ccccc34)C[CH]C12 | C1NCc2c1ccc1[nH]c3ccccc3c21 | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | Other | C1CCOC1.CO | null | null | COc1ccc2c(c1)c1c(n2CCCO[Si](C)(C)C(C)(C)C)CC(c2ccccc2OC)C2C(=O)NC(=O)C12>C1CCOC1.CO>COc1ccc2c(c1)c1c3c(c(-c4ccccc4OC)cc1n2CCCO)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8c86a68d22c44256bfbf666ba786b6a7 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4OC)cc1n2CCCO)C(=O)NC3=O>>O=C1NC(=O)c2c1c(-c1ccccc1O)cc1c2c2cc(O)ccc2n1CCCO | B(Br)(Br)Br.OCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)OC)C(NC3=O)=O)OC>>OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCCO)C1=C(C=CC=C1)O)C(NC4=O)=O | C[O:15][c:14]1[c:9](-[c:8]2[c:7]3[c:6]([c:18]4[c:17]([cH:16]2)[n:26]([CH2:27][CH2:28][CH2:29][OH:30])[c:25]2[c:19]4[cH:20][c:21]([O:22]C)[cH:23][cH:24]2)[C:4](=[O:5])[NH:3][C:2]3=[O:1])[cH:10][cH:11][cH:12][cH:13]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[OH:15])[cH:1... | COc1ccc2c(c1)c1c3c(c(-c4ccccc4OC)cc1n2CCCO)C(=O)NC3=O | O=C1NC(=O)c2c1c(-c1ccccc1O)cc1c2c2cc(O)ccc2n1CCCO | null | null | null | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].C-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8] | 82 | [{"value": 82.0, "product": "OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCCO)C1=C(C=CC=C1)O)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 6-(3-Hydroxypropyl)-9-methoxy-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=2-methoxyphenyl, R10═CH2CH2CH2OH) (100) prepared as described in example 53 with BBr3 using the procedure described in example 80 gave 9-Hydroxy-4-(2-hydroxyphenyl)-6-(3-hydroxypropyl)pyrrolo[3,4-c]carbazole... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.C1NCc2c1ccc1nc3ccccc3c21 | Other | null | null | null | COc1ccc2c(c1)c1c3c(c(-c4ccccc4OC)cc1n2CCCO)C(=O)NC3=O>>O=C1NC(=O)c2c1c(-c1ccccc1O)cc1c2c2cc(O)ccc2n1CCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f0c7b50e2fa14884897237926ba5e44f | COc1ccc2c(c1)cc(C=Cc1c(Cl)cccc1OC)n2CCCO[Si](C)(C)C(C)(C)C.O=C1C=CC(=O)N1>>COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(c1c(Cl)cccc1OC)C3.COc1ccc2c(c1)c1c(n2CCCO[Si](C)(C)C(C)(C)C)CC(c2ccccc2OC)C2C(=O)NC(=O)C12 | [Si](C)(C)(C(C)(C)C)OCCCN1C(=CC2=CC(=CC=C12)OC)C=CC1=C(C=CC=C1OC)Cl.C1(C=CC(N1)=O)=O>>ClC1=C(C(=CC=C1)OC)C1CC=2NC=3C=CC(=CC3C2C2C1C(NC2=O)=O)OC.[Si](C)(C)(C(C)(C)C)OCCCN1C=2C=CC(=CC2C=2C3C(C(CC12)C1=C(C=CC=C1)OC)C(NC3=O)=O)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[n:7]([CH2:41][CH2:42][CH2:43][O:44][Si:45]([CH3:30])([CH3:46])[C:48]([CH3:32])([CH3:54])[CH3:61])[c:8]([CH:29]=[CH:19][c:20]3[c:21]([Cl:22])[cH:23][cH:24][cH:25][c:26]3[O:27][CH3:28])[cH:9][c:10]2[cH:11]1.[CH:12]1=[CH:18][C:16](=[O:17])[NH:65][C:13]1=[O:14]>>[CH3:1][O:2][c:3]1[cH:4]... | COc1ccc2c(c1)cc(C=Cc1c(Cl)cccc1OC)n2CCCO[Si](C)(C)C(C)(C)C.O=C1C=CC(=O)N1 | COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(c1c(Cl)cccc1OC)C3.COc1ccc2c(c1)c1c(n2CCCO[Si](C)(C)C(C)(C)C)CC(c2ccccc2OC)C2C(=O)NC(=O)C12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 77637d3f56cf458fa41066d1ab85ec4037cd542b079618bf456dc29c2759bfbf | e1caee8150cf72ecc4e201ba67ee2f6069c0684cf1dd043ad87dc208401efdcf | O=C1NC(=O)C2C(c3ccccc3)Cc3[nH]c4ccccc4c3C12.O=C1NC(=O)C2C(c3ccccc3)Cc3[nH]c4ccccc4c3C12 | [C;D1;H3:1]-[Si;H0;D4;+0:2](-[CH3;D1;+0:3])(-[#8:4]-[C:5]-[C:6]-[CH2;D2;+0:7]-[n;H0;D3;+0:8]1:[c:9](:[c:10]):[c:11](:[c:12]):[cH;D2;+0:13]:[c:14]:1-[CH;D2;+0:15]=[CH;D2;+0:16]-[c:17](:[c:18]):[c:19])-[C;H0;D4;+0:20](-[CH3;D1;+0:21])(-[CH3;D1;+0:22])-[CH3;D1;+0:23].[O;D1;H0:24]=[C;H0;D3;+0:25]1-[CH;D2;+0:26]=[CH;D2;+0:2... | null | [] | null | null | null | null | The reaction of 1-(3-{[tert-Butyl(dimethyl)silyl]oxy}propyl)-2-[2-(2-chloro-6-methoxyphenyl)ethenyl]-5-methoxy-1H-indole (III; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2CH2OSiMe2t-Bu) (103) prepared as described in example 56 with maleimide using the procedure described in example 68 gave 6-(3-[tert-Butyl(dimethyl)silyl]o... | 10.6084/m9.figshare.5104873.v1 | null | Unsubstituted dicarboximide.TMS ether protective group | Ether.Ether.Unsubstituted dicarboximide.Unsubstituted dicarboximide.TMS ether protective group | c1ccc2[nH]ccc2c1.C1=CCNC1 | c1ccc2c3c([nH]c2c1)CCC1CNCC31.c1ccccc1.C1NCC2c3c([nH]c4ccccc34)C[CH]C12 | c1ccccc1.c1ccc2c3c([nH]c2c1)CCC1CNCC31.c1ccccc1.C1NCC2c3c([nH]c4ccccc34)C[CH]C12 | Other | null | null | null | COc1ccc2c(c1)cc(C=Cc1c(Cl)cccc1OC)n2CCCO[Si](C)(C)C(C)(C)C.O=C1C=CC(=O)N1>>COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(c1c(Cl)cccc1OC)C3.COc1ccc2c(c1)c1c(n2CCCO[Si](C)(C)C(C)(C)C)CC(c2ccccc2OC)C2C(=O)NC(=O)C12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8af552d326f44e5488dc65134040e607 | COc1ccc2c(c1)c1c(n2CCCO[Si](C)(C)C(C)(C)C)CC(c2c(Cl)cccc2OC)C2C(=O)NC(=O)C12>>COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4OC)cc1n2CCCO)C(=O)NC3=O | C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N.Cl.[Si](C)(C)(C(C)(C)C)OCCCN1C=2C=CC(=CC2C=2C3C(C(CC12)C1=C(C=CC=C1OC)Cl)C(NC3=O)=O)OC.[Si](C)(C)(C(C)(C)C)OCCCN1C=2C=CC(=CC2C=2C3C(C(CC12)C1=C(C=CC=C1)OC)C(NC3=O)=O)OC>>ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCCO | CC(C)(C)[Si](C)(C)[O:28][CH2:27][CH2:26][CH2:25][n:24]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]2[c:9]2[c:23]1[CH2:22][CH:12]([c:13]1[c:14]([Cl:15])[cH:16][cH:17][cH:18][c:19]1[O:20][CH3:21])[CH:11]1[CH:10]2[C:32](=[O:33])[NH:31][C:29]1=[O:30]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[c:9]1[c:10]3[c:11... | COc1ccc2c(c1)c1c(n2CCCO[Si](C)(C)C(C)(C)C)CC(c2c(Cl)cccc2OC)C2C(=O)NC(=O)C12 | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4OC)cc1n2CCCO)C(=O)NC3=O | null | null | C1CCOC1.CO | Miscellaneous | OtherReaction | 6c9712e00c7b4d1c5f8a072ac030d252cf1631f2fe61823cdac905a14569b28d | 8810278526f6a2c0e6c6bc11dce581d57652dfa7eee92b5b7a2e8cacd394ef1e | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]-[C:4]-[#7;a:5]1:[c:6]:[c:7]:[c:8]2:[c:9]:1-[CH2;D2;+0:10]-[CH;D3;+0:11](-[c;H0;D3;+0:12](:[c:13](-[Cl;D1;H0:14]):[c:15]):[c:16](-[#8:17]):[c:18])-[CH;D3;+0:19]1-[C:20](=[O;D1;H0:21])-[#7:22]-[C:23](=[O;D1;H0:24])-[CH;D3;+0:25]-1-2>>[#8:17]-[c:16](:[c:18]):[c;H0;D3;+0:... | 76 | [{"value": 76.0, "product": "ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 6-(3-{[tert-Butyl(dimethyl)silyl]oxy}propyl)-4-(2-chloro-6-methoxyphenyl)-9-methoxy-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dione (IV; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2CH2OSiMe2t-Bu) (104) prepared as described in example 57 with DDQ using the procedure described in example 70 foll... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Primary alcohol | C1NCC2c3c([nH]c4ccccc34)C[CH]C12 | C1NCc2c1ccc1[nH]c3ccccc3c21 | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | Other | C1CCOC1.CO | null | null | COc1ccc2c(c1)c1c(n2CCCO[Si](C)(C)C(C)(C)C)CC(c2c(Cl)cccc2OC)C2C(=O)NC(=O)C12>C1CCOC1.CO>COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4OC)cc1n2CCCO)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-60079b1f24ca45af8dc55a802fe52b64 | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4OC)cc1n2CCCO)C(=O)NC3=O>>COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCCO | B(Br)(Br)Br.ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCCO>>ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCCO | C[O:24][c:23]1[cH:22][c:21]2[c:13]3[c:12]([cH:11][c:10](-[c:9]4[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]4[Cl:8])[c:15]4[c:14]3[C:19](=[O:20])[NH:18][C:16]4=[O:17])[n:28]([CH2:29][CH2:30][CH2:31][OH:32])[c:27]2[cH:26][cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([Cl:8])[c:9]1-[c:10]1[cH:11][c:12]2[c:13]([c:14]3[c... | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4OC)cc1n2CCCO)C(=O)NC3=O | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCCO | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 64 | [{"value": 64.0, "product": "ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 4-(2-Chloro-6-methoxyphenyl)-6-(3-hydroxypropyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2CH2OH) (105) prepared as described in example 58 with BBr3 using the procedure described in example 80 and with a reaction time of 90 minutes gave 4-(2-Chloro-6-m... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1NCc2c1ccc1nc3ccccc3c21 | Other | null | null | null | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4OC)cc1n2CCCO)C(=O)NC3=O>>COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fc288b67d39b4f6c88905d219fdffbcc | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCCO>>COc1ccccc1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCCO | C(C)(=O)[O-].[K+].C(C)(=O)OCC.ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCCO>>OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCCO)C1=C(C=CC=C1)OC)C(NC4=O)=O | Cl[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:8]1-[c:9]1[cH:10][c:11]2[c:12]([c:13]3[c:14]1[C:15](=[O:16])[NH:17][C:18]3=[O:19])[c:20]1[cH:21][c:22]([OH:23])[cH:24][cH:25][c:26]1[n:27]2[CH2:28][CH2:29][CH2:30][OH:31]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][c:11]2[c:12]([c:13]3[c:14]1[C:15](=[O... | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCCO | COc1ccccc1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCCO | null | [Pd] | CO | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]):[c:6]>>[c:6]:[c:4](-[c:5]):[cH;D2;+0:1]:[c:2]:[c:3] | 51 | [{"value": 51.0, "product": "OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCCO)C1=C(C=CC=C1)OC)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-(3-hydroxypropyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2CH2OH) (106) (0.20 g, 0.44 mmol) prepared as described in example 59, potassium acetate (0.20 g) and 5% Pd/C in a solution of ethyl acetate (25 ml) and methanol 1:1 (25 mL) unde... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.C1NCc2c1ccc1nc3ccccc3c21 | Other | [Pd].CO | null | null | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCCO>[Pd].CO>COc1ccccc1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-63c40e69daaa436491abcccf68ef7925 | BrCCOC1CCCCO1.CO.COc1ccc2[nH]c(C=Cc3cc([N+](=O)[O-])cc([N+](=O)[O-])c3)cc2c1.Cl>>COc1ccc2c(c1)cc(C=Cc1c(Cl)cccc1OC)n2CCO | Cl.CO.COC=1C=C2C=C(NC2=CC1)C=CC1=CC(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-].O1C(CCCC1)OCCBr>>ClC1=C(C(=CC=C1)OC)C=CC=1N(C2=CC=C(C=C2C1)OC)CCO | Br[CH2:23][CH2:24][O:25]C1CCCCO1.[OH:20][CH3:21].O=[N+]([O-])[c:16]1[cH:14][c:13]([CH:12]=[CH:11][c:10]2[cH:9][c:7]3[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]3)[nH:22]2)[cH:19][c:18]([N+](=O)[O-])[cH:17]1.[ClH:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[cH:9][c:10]([CH:11]=[CH:12][c:13]1[c:14]([Cl:15])[cH:... | BrCCOC1CCCCO1.CO.COc1ccc2[nH]c(C=Cc3cc([N+](=O)[O-])cc([N+](=O)[O-])c3)cc2c1.Cl | COc1ccc2c(c1)cc(C=Cc1c(Cl)cccc1OC)n2CCO | null | null | null | Functional Group Interconversion | OtherReaction | a419d81db6f99e9d0494792c4f406383d69616ad2500e2368e8bf456988baae9 | 26ce142e37b6cc0d2165819e413d601e69939fd62f0db7d84e117e5a685c3a1b | C(=Cc1cc2ccccc2[nH]1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-C1-C-C-C-C-O-1.O=[N+](-[O-])-[c;H0;D3;+0:4]1:[c:5]:[c;H0;D3;+0:6](-[N+](=O)-[O-]):[cH;D2;+0:7]:[c:8](-[C:9]=[C:10]-[c:11]2:[c:12]:[c:13]:[c:14](:[c:15]):[nH;D2;+0:16]:2):[cH;D2;+0:17]:1.[C;D1;H3:18]-[OH;D1;+0:19].[ClH;D0;+0:20]>>[C;D1;H3:18]-[O;H0;D2;+0:19]-[c;H0;D3;+0:7]1:[cH;D2;+... | 91 | [{"value": 91.0, "product": "ClC1=C(C(=CC=C1)OC)C=CC=1N(C2=CC=C(C=C2C1)OC)CCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The reaction of 2-[2-(2-Chloro-6-methoxyphenyl)ethenyl]-5-methoxy-1H-indole (II; Ar=2-chloro-6-methoxyphenyl) (102) prepared as described in example 55 with 2-bromoethyl tetrahydro-2H-pyran-2-yl ether using the procedure described in example 38 followed by reaction of the crude product with 2N HCl in methanol gave 2-{2... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Ether.Nitro group.Nitro group.Methanol | Aromatic halide.Ether.Primary alcohol | C1CCOCC1.c1ccccc1.c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HBr | null | null | null | BrCCOC1CCCCO1.CO.COc1ccc2[nH]c(C=Cc3cc([N+](=O)[O-])cc([N+](=O)[O-])c3)cc2c1.Cl>>COc1ccc2c(c1)cc(C=Cc1c(Cl)cccc1OC)n2CCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b19c236e376842cc819929ad988edb6a | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4OC)cc1n2CCO)C(=O)NC3=O>>COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCO | B(Br)(Br)Br.ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCO>>ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCO | C[O:24][c:23]1[cH:22][c:21]2[c:13]3[c:12]([cH:11][c:10](-[c:9]4[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]4[Cl:8])[c:15]4[c:14]3[C:19](=[O:20])[NH:18][C:16]4=[O:17])[n:28]([CH2:29][CH2:30][OH:31])[c:27]2[cH:26][cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([Cl:8])[c:9]1-[c:10]1[cH:11][c:12]2[c:13]([c:14]3[c:15]1[C:... | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4OC)cc1n2CCO)C(=O)NC3=O | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCO | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 56 | [{"value": 56.0, "product": "ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The reaction of 4-(2-Chloro-6-methoxyphenyl)-6-(2-hydroxyethyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2OH) (111) prepared as described in example 63 with BBr3 using the procedure described in example 80 except that the reaction conditions were 2 h at 0° C. gave 4-(2... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1NCc2c1ccc1nc3ccccc3c21 | Other | null | null | 2 | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4OC)cc1n2CCO)C(=O)NC3=O>>COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4f79f664c86445d28a8aee5c0bd56414 | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCO>>COc1ccccc1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCO | [H][H].ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCO>>OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCO)C1=C(C=CC=C1)OC)C(NC4=O)=O | Cl[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:8]1-[c:9]1[cH:10][c:11]2[c:12]([c:13]3[c:14]1[C:15](=[O:16])[NH:17][C:18]3=[O:19])[c:20]1[cH:21][c:22]([OH:23])[cH:24][cH:25][c:26]1[n:27]2[CH2:28][CH2:29][OH:30]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9]1[cH:10][c:11]2[c:12]([c:13]3[c:14]1[C:15](=[O:16])[NH... | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCO | COc1ccccc1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCO | null | [Pd] | null | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]):[c:6]>>[c:6]:[c:4](-[c:5]):[cH;D2;+0:1]:[c:2]:[c:3] | 77 | [{"value": 77.0, "product": "OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCO)C1=C(C=CC=C1)OC)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-(2-hydroxyethyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar-2-chloro-6-methoxyphenyl, R10═CH2CH,OH) (112) prepared as described in example 64 with hydrogen gas, using a Pd/C catalyst, according to the procedure for example 60 gave 9-Hydroxy-6-(2-hydroxyethyl)-4-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.C1NCc2c1ccc1nc3ccccc3c21 | Other | [Pd] | null | null | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCO>[Pd]>COc1ccccc1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c617c646dab4d34a16f55b00127ee4c | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4OC)cc1n2CCO)C(=O)NC3=O.CS(=O)(=O)Cl>>COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCOS(C)(=O)=O | B(Br)(Br)Br.ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCO.COC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C(=O)OCC1=CC=CC=C1)C(NC4=O)=O.CS(=O)(=O)Cl>>CS(=O)(=O)OCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1OC)Cl)C(NC3=O)=O)O | C[O:24][c:23]1[cH:22][c:21]2[c:13]3[c:12]([cH:11][c:10](-[c:9]4[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]4[Cl:8])[c:15]4[c:14]3[C:19](=[O:20])[NH:18][C:16]4=[O:17])[n:28]([CH2:29][CH2:30][OH:31])[c:27]2[cH:26][cH:25]1.Cl[S:32]([CH3:33])(=[O:34])=[O:35]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([Cl:8])[c:9]1-[c:10]1[cH... | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4OC)cc1n2CCO)C(=O)NC3=O.CS(=O)(=O)Cl | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCOS(C)(=O)=O | null | null | null | Acylation | OtherReaction | 67bdcf4d596d39c5c19b0d52e73816be61dfa15d3d0e73b49ae2817f6b54da59 | 612c49341ea364c8025430031377b6efe91bae2e03711ce0a04ad7326cb56818 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[OH;D1;+0:7].Cl-[S;H0;D4;+0:8](-[C;D1;H3:9])(=[O;D1;H0:10])=[O;D1;H0:11]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:8](-[C;D1;H3:9])(=[O;D1;H0:10])=[O;D1;H0:11].[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | Reaction of 4-(2-Chloro-6-methoxyphenyl)-6-(2-hydroxyethyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2OH) (111) prepared as described in example 63 with methanesulphonyl chloride, followed by reaction with BBr3 using the procedure described in example 170 of Scheme 3 g... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary alcohol.Sulfonyl halide | Mesylate.Aromatic alcohol | null | null | c1ccccc1.C1NCc2c1ccc1nc3ccccc3c21 | HCl | null | null | null | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4OC)cc1n2CCO)C(=O)NC3=O.CS(=O)(=O)Cl>>COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCOS(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-915b6fcb2b644f1a8f05948a5bd18cc0 | C1COCCN1.COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCOS(C)(=O)=O>>COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCN1CCOCC1 | CS(=O)(=O)OCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1OC)Cl)C(NC3=O)=O)O.N1CCOCC1.COC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C(=O)OCC1=CC=CC=C1)C(NC4=O)=O>>ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCN2CCOCC2 | [NH:31]1[CH2:32][CH2:33][O:34][CH2:35][CH2:36]1.CS(=O)(=O)O[CH2:30][CH2:29][n:28]1[c:12]2[cH:11][c:10](-[c:9]3[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]3[Cl:8])[c:15]3[c:14]([c:13]2[c:21]2[cH:22][c:23]([OH:24])[cH:25][cH:26][c:27]21)[C:19](=[O:20])[NH:18][C:16]3=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([Cl:8])... | C1COCCN1.COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCOS(C)(=O)=O | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCN1CCOCC1 | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | d65566d5f2049ef4dc70d5c480ea5af77518b25af8327af37e9d6d45c6baf558 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2ccccc2n1CCN1CCOCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#7;a:3].[#8:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[#7;a:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#8:4]-[C:9]-[C:8]-1 | 81 | [{"value": 81.0, "product": "ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 2-(4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)ethyl methanesulfonate (VII; Ar=2-chloro-6-methoxyphenyl, n=2, mesylate) (114) prepared as described in example 66 with morpholine using the procedure described in example 179 of Scheme 3 gave 4-(2-Chloro-6-metho... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1.C1NCc2c1ccc1nc3ccccc3c21 | MsOH.HO- | null | null | null | C1COCCN1.COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCOS(C)(=O)=O>>COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCN1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-94ffd459294f4be38a5e0da8180f5b07 | C1CCOC1.COc1ccc([N+](=O)[O-])cc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O>>COc1ccc(N)cc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O.COc1ccc([N+](=O)[O-])cc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | C1CCOC1.Cl.OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC(=C1)[N+](=O)[O-])OC)C(NC4=O)=O.Cl>>NC=1C=CC(=C(C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)OC.OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC(=C1)[N+](=O)[O-])OC)C(NC4=O)=O | [CH2:1]1[O:2][CH2:17][CH2:34][CH2:38]1.[c:6]1([N+:7]([O-:37])=[O:55])[cH:8][c:9](-[c:10]2[cH:11][c:12]3[nH:13][c:44]4[cH:45][cH:46][c:47]([OH:48])[cH:49][c:50]4[c:21]3[c:22]3[c:23]2[C:24](=[O:25])[NH:26][C:27]3=[O:28])[c:31]([O:30][CH3:29])[cH:32][cH:33]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:8][c:9]1-[c:10]... | C1CCOC1.COc1ccc([N+](=O)[O-])cc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | COc1ccc(N)cc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O.COc1ccc([N+](=O)[O-])cc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O | null | B#[Ni] | CO | Aromatic Heterocycle Formation | OtherReaction | 24cb48caead4af5477eb428d6a329c00acbc966b236385afa426c1e363a355a6 | e8ec873f1d7d2668181feaf329978a3d2ba96201f1f0a58688fd21dc7ebce832 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21.O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | [C;D1;H3:1]-[#8:2]-[c;H0;D3;+0:3]1:[c:4]:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[N+;H0;D3:7](-[O-;H0;D1:8])=[O;H0;D1;+0:9]):[c:10]:[c;H0;D3;+0:11]:1-[c:12]1:[c:13]:[c:14]2:[nH;D2;+0:15]:[c;H0;D3;+0:16]3:[c:17]:[c:18]:[c:19]:[c:20]:[c;H0;D3;+0:21]:3:[c;H0;D3;+0:22]:2:[c:23]2:[c:24]:1-[C:25](=[O;D1;H0:26])-[#7:27]-[C:28]-2=[O;D1;H... | null | [] | 60 | CELSIUS | null | null | To a solution of 9-hydroxy-4-(2-methoxy-5-nitrophenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar=2-methoxy-5-nitrophenyl, R10═H) (38) (64 mg, 0.159 mmol) prepared according to example 72 in methanol (10 mL) and THF (1 mL) was added 2N HCl (1 mL) Freshly prepared nickel boride (˜0.50 g) was added and the mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Nitro group | Ether.Ether.Unsubstituted dicarboximide.Nitro group.Aromatic alcohol.Primary amine | C1CCOC1.c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3.c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3.c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | Other | B#[Ni].CO | 60 | null | C1CCOC1.COc1ccc([N+](=O)[O-])cc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O>B#[Ni].CO>COc1ccc(N)cc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O.COc1ccc([N+](=O)[O-])cc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-624945cdd7dc40bf82e1a9c34cf99862 | COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(c1ccccc1Cl)C3>>COc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O | ClC1=C(C=CC=C1)C1CC=2NC=3C=CC(=CC3C2C2C1C(NC2=O)=O)OC.[Si](C)(C)(C(C)(C)C)OCCCN1C=2C=CC(=CC2C=2C3C(C(CC12)C1=C(C=CC=C1)OC)C(NC3=O)=O)OC.ClC1=C(C=CC=C1)C1CC=2NC=3C=CC(=CC3C2C2C1C(NC2=O)=O)OC>>ClC1=C(C=CC=C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[c:20]([c:21]2[cH:22]1)[CH:19]1[CH:18]([CH:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[Cl:17])[CH2:9]3)[C:26](=[O:27])[NH:25][C:23]1=[O:24]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[cH:9][c:10](-[c:11]4[cH:12][cH:13][cH:14][cH:15][c:16]4[Cl:17])[c:18]4[c:19]([c... | COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(c1ccccc1Cl)C3 | COc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O | null | [O-2].[O-2].[Mn+4] | O1CCOCC1 | Oxidation | OtherReaction | 3d157ee1e52021ba4f102c0e4bf23d31153db03cc8f65d6ae2d3bbc53db1b830 | 82a3692de44364afcfd8cc4460435180e0752c31812bf6008d75e02664a32947 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | [Cl;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[c:7]2:[#7;a:8]:[c:9]:[c:10]:[c:11]:2-[CH;D3;+0:12]2-[C:13](=[O;D1;H0:14])-[#7:15]-[C:16](=[O;D1;H0:17])-[CH;D3;+0:18]-1-2):[c:19]:[c:20]>>[Cl;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]2:[#7;a:8]:[c:9]:[c:10]:[c:11]:2:... | null | [] | null | null | 16 | HOUR | Manganese dioxide (12.0 g) was added to a solution of 4-(2-Chlorophenyl)-9-methoxy-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dione (IV; Ar=2-chlorophenyl, R10═H (32) prepared as described in example 68 (2.1 g, 5.51 mmol) in dioxane (100 mL) and the mixture was refluxed with stirring for 16 h. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c3c([nH]c2c1)CCC1CNCC31 | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | null | [O-2].[O-2].[Mn+4].O1CCOCC1 | null | 16 | COc1ccc2[nH]c3c(c2c1)C1C(=O)NC(=O)C1C(c1ccccc1Cl)C3>[O-2].[O-2].[Mn+4].O1CCOCC1>COc1ccc2[nH]c3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8ee1968d724d49868e7cadce4af9eada | COc1ccc2[nH]c(C=Cc3cc([N+](=O)[O-])cc([N+](=O)[O-])c3)cc2c1.COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCCO)C(=O)NC3=O.O=C([O-])O>>COc1ccc([N+](=O)[O-])cc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O.O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCO | B(Br)(Br)Br.ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCCO.C(=O)(O)[O-].[Na+].O.COC=1C=C2C=C(NC2=CC1)C=CC1=CC(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-]>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCCO.OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC(=C1)[N+](=O)[O-])OC)C(NC4=O)=O | [O-][N+:33]([c:4]1[cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]([CH:12]=[CH:13][c:14]2[nH:15][c:16]3[cH:17][cH:18][c:19]([O:2][CH3:1])[cH:21][c:22]3[cH:23]2)[cH:24]1)=[O:35].[CH3:3][O:52][c:51]1[cH:50][c:49]2[c:48]3[c:36]4[c:37]([c:38](-[c:39]5[cH:40][cH:41][cH:42][cH:43][c:44]5[Cl:45])[cH:46][c:47]3[n:56]([CH2:57][CH... | COc1ccc2[nH]c(C=Cc3cc([N+](=O)[O-])cc([N+](=O)[O-])c3)cc2c1.COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCCO)C(=O)NC3=O.O=C([O-])O | COc1ccc([N+](=O)[O-])cc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O.O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCO | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | b0aa36dc88b7b8fc7b234668e1ea4dbf66580ec1eca181530addacc47e8e098f | 285b97627062e5437bdecc02dda67f0b12cb80b7e2a471ada0633a465c5f92dc | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21.O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | O-[C;H0;D3;+0:1](-[O-;H0;D1:2])=[O;D1;H0:3].[C;D1;H3:4]-[O;H0;D2;+0:5]-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c:9]2:[#7;a:10]:[c:11](-[CH;D2;+0:12]=[CH;D2;+0:13]-[c;H0;D3;+0:14]3:[c:15]:[c:16]:[c:17]:[c;H0;D3;+0:18](-[N+;H0;D3:19](-[O-])=[O;H0;D1;+0:20]):[cH;D2;+0:21]:3):[cH;D2;+0:22]:[c:23]:2:[c:24]:1.[C:25]-[#7;a:26]1:[c:27]:[... | null | [] | null | null | 3 | HOUR | A solution of 1N BBr3 in CH2Cl2 (11.5 mL, 0.011 mol) was added to a solution of 4-(2-Chlorophenyl)-6-(3-hydroxypropyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=2-chlorophenyl, R10═CH2CH2CH2OH) (31) prepared as described in example 40 (1.00 g, 2.30 mmol) in CH2Cl2 under nitrogen and the reaction mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Acid.Ether.Ether.Unsubstituted dicarboximide.Nitro group | Ether.Unsubstituted dicarboximide.Unsubstituted dicarboximide.Aromatic alcohol.Aromatic alcohol | c1ccccc1.c1ccc2[nH]ccc2c1.C1NCc2c1ccc1[nH]c3ccccc3c21 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3.C1NCc2c1ccc1nc3ccccc3c21 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3.c1ccccc1.C1NCc2c1ccc1nc3ccccc3c21 | null | C(Cl)Cl | null | 3 | COc1ccc2[nH]c(C=Cc3cc([N+](=O)[O-])cc([N+](=O)[O-])c3)cc2c1.COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCCO)C(=O)NC3=O.O=C([O-])O>C(Cl)Cl>COc1ccc([N+](=O)[O-])cc1-c1cc2[nH]c3ccc(O)cc3c2c2c1C(=O)NC2=O.O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3f6e1d2b349c474fa6a16a0f93f62613 | BrCCOC1CCCCO1.COc1ccc2[nH]c(/C=C/c3ccc([N+](=O)[O-])cc3Br)cc2c1.O=C1C=CC(=O)N1>>COc1ccc2c(c1)c1c3c(c(-c4ccccc4)cc1n2CCO)C(=O)NC3=O | C1(=CC=C(C=C1)S(=O)(=O)O)C.BrC1=C(C=CC(=C1)[N+](=O)[O-])/C=C/C=1NC2=CC=C(C=C2C1)OC.BrCCOC1OCCCC1.C1(C=CC(N1)=O)=O>>OCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)OC | Br[CH2:22][CH2:23][O:24][CH:13]1O[CH2:17][CH2:16][CH2:15][CH2:14]1.O=[N+]([O-])c1c[cH:10][c:11](/[CH:12]=[CH:19]/[c:20]2[cH:9][c:7]3[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]3)[nH:21]2)[c:18](Br)c1.C1=C[C:28](=[O:29])[NH:27][C:25]1=[O:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[c:9]1[c:10]3[c:11]([c:12](-[... | BrCCOC1CCCCO1.COc1ccc2[nH]c(/C=C/c3ccc([N+](=O)[O-])cc3Br)cc2c1.O=C1C=CC(=O)N1 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4)cc1n2CCO)C(=O)NC3=O | null | null | CO.O | Functional Group Interconversion | OtherReaction | 6e82cd7df1922012ed4baa109595c52e05a2e1d183aad57859993f24b4d960a7 | 429670d348dbe5d5eb00efb5ffc8485353034416000e99d901dbdc174ea1ab0e | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | Br-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-[CH;D3;+0:4]1-O-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH2;D2;+0:8]-1.Br-[c;H0;D3;+0:9]1:c:c(-[N+](=O)-[O-]):c:[cH;D2;+0:10]:[c;H0;D3;+0:11]:1/[CH;D2;+0:12]=[CH;D2;+0:13]/[c:14]1:[cH;D2;+0:15]:[c:16](:[c:17]):[c:18](:[c:19]):[nH;D2;+0:20]:1.[O;D1;H0:21]=[C;H0;D3;+0:22]1-C=C-[C;... | null | [] | 50 | CELSIUS | null | null | 5-methoxy-2-[(E,Z)-2-phenylethenyl]-1H-indole (II; Ar=phenyl) (1.93 g, 7.74 mmol was reacted with 2-(2-bromoethoxy)tetrahydro-2H-pyran using the procedure described in example 38. This material was reacted directly with maleimide (0.79 g) using the procedure described in method 4. The product obtained was reacted using... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Ether.Ether.Unsubstituted dicarboximide.Nitro group | Unsubstituted dicarboximide.Primary alcohol | C1CCOCC1.c1ccccc1.c1ccc2[nH]ccc2c1.C1=CCNC1 | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | HBr | CO.O | 50 | null | BrCCOC1CCCCO1.COc1ccc2[nH]c(/C=C/c3ccc([N+](=O)[O-])cc3Br)cc2c1.O=C1C=CC(=O)N1>CO.O>COc1ccc2c(c1)c1c3c(c(-c4ccccc4)cc1n2CCO)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f61fe06652e1483ba61e938ea5e32000 | CC(C)(C)[Si](C)(C)OCCCBr.COc1ccc2[nH]c(/C=C/c3ccc([N+](=O)[O-])cc3Br)cc2c1.O=C1C=CC(=O)N1>>COc1ccc2c(c1)c1c3c(c(-c4ccccc4)cc1n2CCCO)C(=O)NC3=O | BrC1=C(C=CC(=C1)[N+](=O)[O-])/C=C/C=1NC2=CC=C(C=C2C1)OC.[Si](C)(C)(C(C)(C)C)OCCCBr.C1(C=CC(N1)=O)=O>>OCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)OC | CC(C)(C)[Si](C)(C)[O:25][CH2:24][CH2:23][CH2:22]Br.O=[N+]([O-])[c:16]1[cH:15][cH:14][c:13](/[CH:12]=[CH:19]/[c:20]2[cH:9][c:7]3[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]3)[nH:21]2)[c:18](Br)[cH:17]1.[CH:10]1=[CH:11][C:26](=[O:27])[NH:28][C:29]1=[O:30]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[c:9]1[c:10]3[c:... | CC(C)(C)[Si](C)(C)OCCCBr.COc1ccc2[nH]c(/C=C/c3ccc([N+](=O)[O-])cc3Br)cc2c1.O=C1C=CC(=O)N1 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4)cc1n2CCCO)C(=O)NC3=O | null | null | CO.O.Cl | Aromatic Heterocycle Formation | OtherReaction | 2dd49c3b4854e5e07c031b33231cdc62cc4772db06568e15427e294f7691e7a7 | 8f1489f5ec6e4cca230a581e53e2eec6e42dcfc20031f5625286154fafde4539 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[O;H0;D2;+0:4]-[Si](-C)(-C)-C(-C)(-C)-C.Br-[c;H0;D3;+0:5]1:[c:6]:[c;H0;D3;+0:7](-[N+](=O)-[O-]):[c:8]:[c:9]:[c;H0;D3;+0:10]:1/[CH;D2;+0:11]=[CH;D2;+0:12]/[c:13]1:[cH;D2;+0:14]:[c:15](:[c:16]):[c:17](:[c:18]):[nH;D2;+0:19]:1.[O;D1;H0:20]=[C:21]1-[#7:22]-[C:23](=[O;D1;H0:24])-[CH;D2;+0:25]=[C... | 23 | [{"value": 23.0, "product": "OCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Methoxy-2-[(E,Z)-2-phenylethenyl]-1H-indole (II; Ar=phenyl) (6.85 g, 27.5 mmol) was reacted with with 3-bromopropyl tert-butyl(dimethyl)silyl ether using the procedure described in example 38. The product isolated was reacted directly with maleimide (5.2 g) using the procedure described in example 68. Aromatisation o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide.Nitro group.TMS ether protective group | Primary alcohol | c1ccccc1.c1ccc2[nH]ccc2c1.C1=CCNC1 | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | HBr | CO.O.Cl | null | null | CC(C)(C)[Si](C)(C)OCCCBr.COc1ccc2[nH]c(/C=C/c3ccc([N+](=O)[O-])cc3Br)cc2c1.O=C1C=CC(=O)N1>CO.O.Cl>COc1ccc2c(c1)c1c3c(c(-c4ccccc4)cc1n2CCCO)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-612d771bad9043279bcecec1cba7a604 | C=CC#N.COc1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1>>COc1ccc2c(c1)cc(/C=C/c1ccccc1Cl)n2CCC#N | C(C=C)#N.ClC1=C(C=CC=C1)C=CC=1NC2=CC=C(C=C2C1)OC.OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C1=C(C=CC(=C1)[N+](=O)[O-])O)C(NC4=O)=O>>ClC1=C(C=CC=C1)/C=C/C=1N(C2=CC=C(C=C2C1)OC)CCC#N | [CH2:21]=[CH:22][C:23]#[N:24].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[cH:9][c:10]([CH:11]=[CH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[Cl:19])[nH:20]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[cH:9][c:10](/[CH:11]=[CH:12]/[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[Cl:19])[n:20]2[CH2:21][CH2:22... | C=CC#N.COc1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1 | COc1ccc2c(c1)cc(/C=C/c1ccccc1Cl)n2CCC#N | null | N12CCCCCC2=NCCC1 | O.C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | dbe06308fd0a5047c92f3bac96d8c1a8251ac4669b293e46c18abb750e9b5de1 | 9a626e72af92b4926e3e632773bc972f63cd9f1cf5e0e294f2aa92f80c10ca13 | C(=C/c1cc2ccccc2[nH]1)\c1ccccc1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[C:3]#[N;D1;H0:4].[c:5]-[C:6]=[C:7]-[c:8]1:[c:9]:[c:10]:[c:11](:[c:12]):[nH;D2;+0:13]:1>>[N;D1;H0:4]#[C:3]-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:13]1:[c:8](/[C:7]=[C:6]/[c:5]):[c:9]:[c:10]:[c:11]:1:[c:12] | 77 | [{"value": 77.0, "product": "ClC1=C(C=CC=C1)/C=C/C=1N(C2=CC=C(C=C2C1)OC)CCC#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of trans-diene (27) prepared as described in example 37 (1.5 g, 5.25 mmol) in acetonitrile (30 mL) was added acrylonitrile (2.42 mL, 36.8 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (20 drops). The resulting solution was stirred at room temperature under nitrogen for 18 h before being diluted with water ... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | null | N12CCCCCC2=NCCC1.O.C(C)#N | null | 18 | C=CC#N.COc1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1>N12CCCCCC2=NCCC1.O.C(C)#N>COc1ccc2c(c1)cc(/C=C/c1ccccc1Cl)n2CCC#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8450601e0b244db8a4f671e080a931b1 | COc1ccc2c(c1)cc(/C=C/c1ccccc1Cl)n2CCC#N.O=C1C=CC(=O)N1>>COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC#N)C(=O)NC3=O | ClC1=C(C=CC=C1)/C=C/C=1N(C2=CC=C(C=C2C1)OC)CCC#N.C1(C=CC(N1)=O)=O>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC#N | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[cH:9][c:21](/[CH:20]=[CH:12]/[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[Cl:19])[n:22]2[CH2:23][CH2:24][C:25]#[N:26].[CH:10]1=[CH:11][C:27](=[O:28])[NH:29][C:30]1=[O:31]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[c:9]1[c:10]3[c:11]([c:12](-[c:13]4[cH:14][cH:15]... | COc1ccc2c(c1)cc(/C=C/c1ccccc1Cl)n2CCC#N.O=C1C=CC(=O)N1 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC#N)C(=O)NC3=O | null | null | null | Miscellaneous | OtherReaction | 06ebd2a4d1c4338655a13edf4585639bd7722f7dc8ca7be18dccccea69c13187 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | [C:1]-[#7;a:2]1:[c:3](/[CH;D2;+0:4]=[CH;D2;+0:5]/[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[Cl;D1;H0:10]):[c:11]):[cH;D2;+0:12]:[c:13](:[c:14]):[c:15]:1:[c:16].[O;D1;H0:17]=[C:18]1-[#7:19]-[C:20](=[O;D1;H0:21])-[CH;D2;+0:22]=[CH;D2;+0:23]-1>>[C:1]-[#7;a:2]1:[c:3]2:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:... | 80.2 | [{"value": 80.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.2, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Diene (236) (1.30 g, 3.86 mmol) prepared as described in example 96 was reacted with maleimide (0.49 g) following The procedure described in example 68 and then aromatized according to the procedure described in example 70 to give crude material that was chromatographed on silica eluting with ethyl acetate/hexane (1:1)... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]ccc2c1.C1=CCNC1 | C1NCc2c1ccc1[nH]c3ccccc3c21 | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | null | null | null | null | COc1ccc2c(c1)cc(/C=C/c1ccccc1Cl)n2CCC#N.O=C1C=CC(=O)N1>>COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC#N)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ac8cb47f4c114e919ab994028c58afaa | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC#N)C(=O)NC3=O>>N#CCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC#N>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC#N | C[O:10][c:9]1[cH:8][cH:7][c:6]2[n:5]([CH2:4][CH2:3][C:2]#[N:1])[c:25]3[c:13]([c:12]2[cH:11]1)[c:14]1[c:15]([c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[Cl:23])[cH:24]3)[C:26](=[O:27])[NH:28][C:29]1=[O:30]>>[N:1]#[C:2][CH2:3][CH2:4][n:5]1[c:6]2[cH:7][cH:8][c:9]([OH:10])[cH:11][c:12]2[c:13]2[c:14]3[c:15]([c:16](-[c... | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC#N)C(=O)NC3=O | N#CCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | null | null | CO | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 89.3 | [{"value": 89.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.3, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Demethylation of nitrile (237) (0.15 g, 0.35 mmol) prepared as described in example 97 employing The procedure described in example 80, followed by trituration from methanol, gave phenol (238) (0.13 g, 89%) as an orange/yellow powder, mp 332–336° C. 1H NMR δ [(CD3)2SO] 11.10 (br s, 1H), 9.42 (br s, 1H), 8.39 (d, J=2.4 ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | Other | CO | null | null | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC#N)C(=O)NC3=O>CO>N#CCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-60c9c68580eb4ab0aadc7efe56b5175a | Cc1c(Cl)cccc1Cl.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>Clc1cccc(Cl)c1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.ClC1=C(C(=CC=C1)Cl)C.BrN1C(CCC1=O)=O>>[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=CC=C1)Cl | [Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([Cl:7])[c:8]1[CH3:9].O=C1CCC(=O)N1[Br:29].[P:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6]([Cl:7])[c:8]1[CH2:9][P+:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][c... | Cc1c(Cl)cccc1Cl.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | Clc1cccc(Cl)c1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] | null | N(=NC(C#N)(C)C)C(C#N)(C)C | C1=CC=CC=C1 | Miscellaneous | OtherReaction | 90798389381727105f8f2fc21b48c935111a22021515f706338ce609a905e694 | 7953bead7af5583757c739601734838d384eb4a189267c5eeec33f580917362a | c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5].[c:6]:[c:7](-[P;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]>>[Br-;H0;D0:1].[c:6]:[c:7](-[P+;H0;D4:8](-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15] | 99 | [{"value": 99.0, "product": "[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=CC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.9, "product": "[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2,6-dichlorotoluene (20.1 g, 0.125 mol), N-bromosuccinimide (24.6 g, 0.138 mol) and 2,2′-azobisisobutyronitrile (0.41 g, 2.50 mmol) in dry benzene (300 mL) under N2 was stirred at reflux for 6 h with continuous irradiation from a 100W lamp. The resulting reaction mixture was concentrated under vacuum (to 5... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | null | C1CCNC1 | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | N(=NC(C#N)(C)C)C(C#N)(C)C.C1=CC=CC=C1 | null | null | Cc1c(Cl)cccc1Cl.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1>N(=NC(C#N)(C)C)C(C#N)(C)C.C1=CC=CC=C1>Clc1cccc(Cl)c1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-09c9625c2f0844eb972125fd587329d8 | COc1ccc2[nH]c(C=O)cc2c1.Clc1cccc(Cl)c1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>COc1ccc2[nH]c(/C=C/c3c(Cl)cccc3Cl)cc2c1 | COC=1C=C2C=C(NC2=CC1)C=O.[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=CC=C1)Cl.[Li+].CC(C)[N-]C(C)C>>ClC1=C(C(=CC=C1)Cl)/C=C/C=1NC2=CC=C(C=C2C1)OC | O=[CH:9][c:8]1[nH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:21][c:20]2[cH:19]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:10][c:11]2[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]2[Cl:18])cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8](/[CH:9]=[CH:10]/[c:11]3[c:12]([Cl:13])[cH:14][cH:15][cH:16][c:17]3[Cl:18])[cH:19][c:20]2[cH... | COc1ccc2[nH]c(C=O)cc2c1.Clc1cccc(Cl)c1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | COc1ccc2[nH]c(/C=C/c3c(Cl)cccc3Cl)cc2c1 | null | null | null | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=C/c1cc2ccccc2[nH]1)\c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[c:6]:[c:7](-[CH2;D2;+0:8]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:9]>>[c:6]:[c:7](/[CH;D2;+0:8]=[CH;D2;+0:1]/[c:2](:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | 5 | HOUR | The 5-methoxy-1H-indole-2-carbaldehyde (O) was reacted with (2,6-dichlorobenzyl)(triphenyl)phosphonium bromide (511) prepared as described in example 102 using the procedure described in example 37, except that the LDA and aldehyde were (sequentially) added at 0° C., the ratio of LDA aldehyde was 1.37:1 and the reactio... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | null | null | 5 | COc1ccc2[nH]c(C=O)cc2c1.Clc1cccc(Cl)c1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>COc1ccc2[nH]c(/C=C/c3c(Cl)cccc3Cl)cc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-62d61bd7e7f844569eafefc807ca8df6 | Cc1c(Br)cccc1Br.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>Brc1cccc(Br)c1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] | BrC1=C(C(=CC=C1)Br)C.C1CC(=O)N(C1=O)Br.CC(C)(C#N)N=NC(C)(C)C#N.[Br-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].BrC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=CC=C1)Br | [Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]([Br:7])[c:8]1[CH3:9].O=C1CCC(=O)N1[Br:29].[P:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]([Br:7])[c:8]1[CH2:9][P+:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][c... | Cc1c(Br)cccc1Br.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | Brc1cccc(Br)c1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] | null | null | C(Cl)Cl.C1=CC=CC=C1 | Miscellaneous | OtherReaction | 90798389381727105f8f2fc21b48c935111a22021515f706338ce609a905e694 | 7953bead7af5583757c739601734838d384eb4a189267c5eeec33f580917362a | c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5].[c:6]:[c:7](-[P;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]>>[Br-;H0;D0:1].[c:6]:[c:7](-[P+;H0;D4:8](-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15] | 95 | [{"value": 95.0, "product": "[Br-].BrC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=CC=C1)Br", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Bromination of 2,6-dibromotoluene with NBS/AIBN, followed by reaction of the crude bromide with triphenylphosphine, using the procedure described in example 102, except that the reaction time for the bromination was 3 h, gave the phosphonium salt (516) (95%) as a cream powder, mp (CH2Cl2/benzene) 241–243° C. 1H NMR (CD... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | null | C1CCNC1 | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl.C1=CC=CC=C1 | null | 3 | Cc1c(Br)cccc1Br.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C(Cl)Cl.C1=CC=CC=C1>Brc1cccc(Br)c1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-59650bb3fb5849e1898bd638217fd9f7 | Brc1cccc(Br)c1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1ccc2[nH]c(/C=C/c3c(Br)cccc3Br)cc2c1 | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.[Br-].BrC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=CC=C1)Br.[Li+].CC(C)[N-]C(C)C>>BrC1=C(C(=CC=C1)Br)/C=C/C=1NC2=CC=C(C=C2C1)OC | c1ccc([P+](c2ccccc2)(c2cccc[cH:1]2)[CH2:10][c:11]2[c:12]([Br:13])[cH:14][cH:15][cH:16][c:17]2[Br:18])cc1.O=C1NC(=O)c2c1c(I)[cH:9][c:8]1[nH:7][c:6]3[cH:5][cH:4][c:3]([OH:2])[cH:21][c:20]3[c:19]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8](/[CH:9]=[CH:10]/[c:11]3[c:12]([Br:13])[cH:14][cH:15][cH:16][c:17]3[Br:18])[c... | Brc1cccc(Br)c1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | COc1ccc2[nH]c(/C=C/c3c(Br)cccc3Br)cc2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 76e526426ecd806adac24971ec22abcee22f8ef37d02feb5b78b4790d43dc040 | 298bbddbbad66b4d8f09c0f74d9ca58c3f96284e4a5a7f4c53c37cace7b0e319 | C(=C/c1cc2ccccc2[nH]1)\c1ccccc1 | I-c1:[cH;D2;+0:1]:[c:2]2:[#7;a:3]:[c:4]3:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]:[c:10]:3:[c;H0;D3;+0:11]:2:c2:c:1-C(=O)-N-C-2=O.[c:12]:[c:13](-[CH2;D2;+0:14]-[P+](-c1:[cH;D2;+0:15]:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:16]>>[CH3;D1;+0:15]-[O;H0;D2;+0:8]-[c:7]1:[c:9]:[c:10]2:[cH;D2;+0:11]:[c:2](/[CH;D2;+0:1]=[C... | null | [] | null | null | 5 | HOUR | The 5-methoxy-1H-indole-2-carbaldehyde (1) was reacted with (2,6-dibromobenzyl)(triphenyl)phosphonium bromide (516) prepared as described in example 107 using the procedure described in example 37, except that the ratio of LDA:aldehyde was 1.37:1 and the reaction time was 5 h, to give (after crystallisation from CH2Cl2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Unsubstituted dicarboximide.Aromatic alcohol | Ether | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HI | null | null | 5 | Brc1cccc(Br)c1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1ccc2[nH]c(/C=C/c3c(Br)cccc3Br)cc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e43bb02ecf6b45f3a5d7445a8e13c68c | Br.COc1cc(Cl)c(CO)c(Cl)c1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>COc1cc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1.[Br-] | ClC1=C(C(=CC(=C1)OC)Cl)CO.Br.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=CC(=C1)OC)Cl | [BrH:31].O[CH2:8][c:7]1[c:5]([Cl:6])[cH:4][c:3]([O:2][CH3:1])[cH:30][c:28]1[Cl:29].[P:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Cl:6])[c:7]([CH2:8][P+:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][cH:1... | Br.COc1cc(Cl)c(CO)c(Cl)c1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | COc1cc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1.[Br-] | null | null | C(C)(=O)O.C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | bbb792e2dbaac6137f4ab4b2ad2edf8b90c54de5f7db3b319a5444b78b4405dc | 5700379a096deb40e2dc50b293f55a01cfe36aa58cf97bdfa006d0b7ff21038e | c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[BrH;D0;+0:5].[c:6]:[c:7](-[P;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]>>[Br-;H0;D0:5].[c:6]:[c:7](-[P+;H0;D4:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15] | 100 | [{"value": 100.0, "product": "[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=CC(=C1)OC)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (2,6-dichloro-4-methoxyphenyl)methanol (3.00 g, 14.5 mmol) in 30% HBr in acetic acid (45 mL) was stirred at 20° C. for 3 h, then poured onto ice-water (120 mL) and extracted with pentane (6×100 mL). The extracts were washed with water (3×200 mL), backextracting with pentane (100 mL). Removal of the solven... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C1=CC=CC=C1 | null | null | Br.COc1cc(Cl)c(CO)c(Cl)c1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C(C)(=O)O.C1=CC=CC=C1>COc1cc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a5188ceed6ed4d199e64c5818e4ba7f6 | COc1cc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1cc(Cl)c(/C=C/c2cc3cc(OC)ccc3[nH]2)c(Cl)c1 | [Li+].CC(C)[N-]C(C)C.OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=CC(=C1)OC)Cl>>ClC1=C(C(=CC(=C1)OC)Cl)/C=C/C=1NC2=CC=C(C=C2C1)OC | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:8][c:7]2[c:5]([Cl:6])[cH:4][c:3]([O:2][CH3:1])[cH:23][c:21]2[Cl:22])cc1.O=C1NC(=O)c2c1c(I)[cH:9][c:10]1[c:11]2[c:12]2[cH:13][c:14]([OH:15])[cH:17][cH:18][c:19]2[nH:20]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([Cl:6])[c:7](/[CH:8]=[CH:9]/[c:10]2[cH:11][c:12]3[cH:13][c:14]([O:15][CH3:16])[cH:17]... | COc1cc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | COc1cc(Cl)c(/C=C/c2cc3cc(OC)ccc3[nH]2)c(Cl)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 76e526426ecd806adac24971ec22abcee22f8ef37d02feb5b78b4790d43dc040 | 298bbddbbad66b4d8f09c0f74d9ca58c3f96284e4a5a7f4c53c37cace7b0e319 | C(=C/c1cc2ccccc2[nH]1)\c1ccccc1 | I-c1:[cH;D2;+0:1]:[c:2]2:[#7;a:3]:[c:4]3:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]:[c:10]:3:[c;H0;D3;+0:11]:2:c2:c:1-C(=O)-N-C-2=O.[c:12]:[c:13](-[CH2;D2;+0:14]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:15]>>[C;D1;H3:16]-[O;H0;D2;+0:8]-[c:7]1:[c:9]:[c:10]2:[cH;D2;+0:11]:[c:2](/[CH;D2;+0:1]=[CH;D2;+0:14]/[c... | null | [] | null | null | 5 | HOUR | The 5-methoxy-1H-indole-2-carbaldehyde (1) was reacted with (2,6-dichloro-4-methoxybenzyl)(triphenyl)phosphonium bromide (521), prepared as described in example 112, using the procedure described in example 37, except that the aldehyde was added at 0° C., the ratio of LDA:aldehyde was 1.37:1 and the reaction time was 5... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Unsubstituted dicarboximide.Aromatic alcohol | Ether | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HI | null | null | 5 | COc1cc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1cc(Cl)c(/C=C/c2cc3cc(OC)ccc3[nH]2)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-45cd2ce8b12c4a538ef3a33a64d2aec4 | Br.COc1ccc(Cl)c(CO)c1Cl.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>COc1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1Cl.[Br-] | ClC1=C(C(=CC=C1OC)Cl)CO.Br.[Br-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=CC=C1OC)Cl | [BrH:31].O[CH2:9][c:8]1[c:6]([Cl:7])[cH:5][cH:4][c:3]([O:2][CH3:1])[c:29]1[Cl:30].[P:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[c:8]([CH2:9][P+:10]([c:11]2[cH:12][cH:13][cH:14][cH:1... | Br.COc1ccc(Cl)c(CO)c1Cl.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | COc1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1Cl.[Br-] | null | null | C(C)(=O)O.C(Cl)Cl.C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | bbb792e2dbaac6137f4ab4b2ad2edf8b90c54de5f7db3b319a5444b78b4405dc | 5700379a096deb40e2dc50b293f55a01cfe36aa58cf97bdfa006d0b7ff21038e | c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[BrH;D0;+0:5].[c:6]:[c:7](-[P;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]>>[Br-;H0;D0:5].[c:6]:[c:7](-[P+;H0;D4:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15] | 97 | [{"value": 97.0, "product": "[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=CC=C1OC)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 36 | HOUR | Bromination of (2,6-dichloro-3-methoxyphenyl)methanol with 30% HBr in acetic acid, followed by reaction of the crude bromide with triphenylphosphine, using the procedure described in example 112, except that the reaction time for the displacement was 36 h, gave the phosphonium salt (526) (97%) as a white solid, mp (CH2... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C(Cl)Cl.C1=CC=CC=C1 | null | 36 | Br.COc1ccc(Cl)c(CO)c1Cl.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C(C)(=O)O.C(Cl)Cl.C1=CC=CC=C1>COc1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1Cl.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b68878edc0094592bc98e8d4a7c9806f | COc1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1Cl.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1ccc2[nH]c(/C=C/c3c(Cl)ccc(OC)c3Cl)cc2c1 | [Li+].CC(C)[N-]C(C)C.OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C(=CC=C1OC)Cl>>ClC1=C(C(=CC=C1OC)Cl)/C=C/C=1NC2=CC=C(C=C2C1)OC | c1ccc([P+](c2ccccc2)(c2cccc[cH:1]2)[CH2:10][c:11]2[c:12]([Cl:13])[cH:14][cH:15][c:16]([O:17][CH3:18])[c:19]2[Cl:20])cc1.O=C1NC(=O)c2c1c(I)[cH:9][c:8]1[nH:7][c:6]3[cH:5][cH:4][c:3]([OH:2])[cH:23][c:22]3[c:21]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8](/[CH:9]=[CH:10]/[c:11]3[c:12]([Cl:13])[cH:14][cH:15][c:16]([O... | COc1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1Cl.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | COc1ccc2[nH]c(/C=C/c3c(Cl)ccc(OC)c3Cl)cc2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 76e526426ecd806adac24971ec22abcee22f8ef37d02feb5b78b4790d43dc040 | 298bbddbbad66b4d8f09c0f74d9ca58c3f96284e4a5a7f4c53c37cace7b0e319 | C(=C/c1cc2ccccc2[nH]1)\c1ccccc1 | I-c1:[cH;D2;+0:1]:[c:2]2:[#7;a:3]:[c:4]3:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]:[c:10]:3:[c;H0;D3;+0:11]:2:c2:c:1-C(=O)-N-C-2=O.[c:12]:[c:13](-[CH2;D2;+0:14]-[P+](-c1:[cH;D2;+0:15]:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:16]>>[CH3;D1;+0:15]-[O;H0;D2;+0:8]-[c:7]1:[c:9]:[c:10]2:[cH;D2;+0:11]:[c:2](/[CH;D2;+0:1]=[C... | null | [] | null | null | 5 | HOUR | The 5-methoxy-1H-indole-2-carbaldehyde (1) was reacted with (2,6-dichloro-3-methoxybenzyl)(triphenyl)phosphonium bromide (526), prepared as described in example 117, using the procedure described in example 37, except that the aldehyde was added at 0° C., the ratio of LDA:aldehyde was 1.55:1 and the reaction time was 5... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Unsubstituted dicarboximide.Aromatic alcohol | Ether | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HI | null | null | 5 | COc1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1Cl.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1ccc2[nH]c(/C=C/c3c(Cl)ccc(OC)c3Cl)cc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1db8bc6974f04497a060aa2801e1f53f | Brc1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1ccc2[nH]c(/C=C/c3ccccc3Br)cc2c1 | [Li+].CC(C)[N-]C(C)C.OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.[Br-].BrC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1>>BrC1=C(C=CC=C1)/C=C/C=1NC2=CC=C(C=C2C1)OC | c1ccc([P+](c2ccccc2)(c2cccc[cH:1]2)[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[Br:17])cc1.O=C1NC(=O)c2c1c(I)[cH:9][c:8]1[nH:7][c:6]3[cH:5][cH:4][c:3]([OH:2])[cH:20][c:19]3[c:18]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8](/[CH:9]=[CH:10]/[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[Br:17])[cH:18][c:19]2[cH:... | Brc1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | COc1ccc2[nH]c(/C=C/c3ccccc3Br)cc2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 76e526426ecd806adac24971ec22abcee22f8ef37d02feb5b78b4790d43dc040 | 298bbddbbad66b4d8f09c0f74d9ca58c3f96284e4a5a7f4c53c37cace7b0e319 | C(=C/c1cc2ccccc2[nH]1)\c1ccccc1 | I-c1:[cH;D2;+0:1]:[c:2]2:[#7;a:3]:[c:4]3:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]:[c:10]:3:[c;H0;D3;+0:11]:2:c2:c:1-C(=O)-N-C-2=O.[c:12]:[c:13](-[CH2;D2;+0:14]-[P+](-c1:[cH;D2;+0:15]:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:16]>>[CH3;D1;+0:15]-[O;H0;D2;+0:8]-[c:7]1:[c:9]:[c:10]2:[cH;D2;+0:11]:[c:2](/[CH;D2;+0:1]=[C... | null | [] | null | null | 5 | HOUR | The 5-methoxy-1H-indole-2-carbaldehyde (1) was reacted with (2-bromobenzyl)(triphenyl)phosphonium bromide using the procedure described in example 37, except that the aldehyde was added at 0° C., the ratio of LDA:aldehyde was 1.46:1 and the reaction time was 5 h, to give (after crystallisation from CH2Cl2/hexane) the d... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Unsubstituted dicarboximide.Aromatic alcohol | Ether | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HI | null | null | 5 | Brc1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1ccc2[nH]c(/C=C/c3ccccc3Br)cc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9657ba143e4645cb9448f995c724a097 | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=[N+]([O-])c1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>COc1ccc2[nH]c(/C=C/c3ccccc3[N+](=O)[O-])cc2c1 | OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.[Cl-].[N+](=O)([O-])C1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1.[Li+].CC(C)[N-]C(C)C>>COC=1C=C2C=C(NC2=CC1)\C=C\C1=C(C=CC=C1)[N+](=O)[O-] | O=C1N[C:1](=O)c2c(I)[cH:9][c:8]3[nH:7][c:6]4[cH:5][cH:4][c:3]([OH:2])[cH:22][c:21]4[c:20]3c21.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[N+:17](=[O:18])[O-:19])cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8](/[CH:9]=[CH:10]/[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[N+:17](=[O... | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=[N+]([O-])c1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | COc1ccc2[nH]c(/C=C/c3ccccc3[N+](=O)[O-])cc2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 76e526426ecd806adac24971ec22abcee22f8ef37d02feb5b78b4790d43dc040 | 298bbddbbad66b4d8f09c0f74d9ca58c3f96284e4a5a7f4c53c37cace7b0e319 | C(=C/c1cc2ccccc2[nH]1)\c1ccccc1 | I-c1:[cH;D2;+0:1]:[c:2]2:[#7;a:3]:[c:4]3:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]:[c:10]:3:[c;H0;D3;+0:11]:2:c2:c:1-[C;H0;D3;+0:12](=O)-N-C-2=O.[c:13]:[c:14](-[CH2;D2;+0:15]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:16]>>[CH3;D1;+0:12]-[O;H0;D2;+0:8]-[c:7]1:[c:9]:[c:10]2:[cH;D2;+0:11]:[c:2](/[CH;D2;+0:1]=... | null | [] | null | null | 5 | HOUR | The 5-methoxy-1H-indole-2-carbaldehyde (1) was reacted with (2-nitrobenzyl)(triphenyl)phosphonium chloride using the procedure described in example 37, except that the ratio of LDA:aldehyde was 1.37:1 and the reaction time was 5 h, to give (after crystallisation from CH2Cl2/hexane) the diene (536) as red-orange crystal... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Unsubstituted dicarboximide.Aromatic alcohol | Ether | c1ccc2c(c1)nc1ccc3c(c12)CNC3.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HI | null | null | 5 | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=[N+]([O-])c1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>COc1ccc2[nH]c(/C=C/c3ccccc3[N+](=O)[O-])cc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a45e48d54ee2440894b7512541d2c34c | Cc1ccccc1C#N.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>N#Cc1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] | C=1(C(=CC=CC1)C#N)C.C1CC(=O)N(C1=O)Br.CC(C)(C#N)N=NC(C)(C)C#N.[Br-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].C(#N)C1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH3:9].O=C1CCC(=O)N1[Br:29].[P:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][P+:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16... | Cc1ccccc1C#N.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | N#Cc1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] | null | null | C(Cl)Cl.C1=CC=CC=C1 | Miscellaneous | OtherReaction | 90798389381727105f8f2fc21b48c935111a22021515f706338ce609a905e694 | 7953bead7af5583757c739601734838d384eb4a189267c5eeec33f580917362a | c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5].[c:6]:[c:7](-[P;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]>>[Br-;H0;D0:1].[c:6]:[c:7](-[P+;H0;D4:8](-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15] | 70 | [{"value": 70.0, "product": "[Br-].C(#N)C1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Bromination of o-tolunitrile with NBS/AIBN, followed by reaction of the crude bromide with triphenylphosphine (1.2 equiv.), using the procedure described in example 102, except that the reaction time for the bromination was 2 h, gave the phosphonium salt (547) (70%) as a light brown powder, mp (CH2Cl2/benzene) 237–241°... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | null | C1CCNC1 | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl.C1=CC=CC=C1 | null | 2 | Cc1ccccc1C#N.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C(Cl)Cl.C1=CC=CC=C1>N#Cc1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a392b1c912f748078ea5ee9702ba2f24 | N#Cc1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1ccc2[nH]c(/C=C/c3ccccc3C#N)cc2c1 | [Li+].CC(C)[N-]C(C)C.OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.[Br-].C(#N)C1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1.[Li+].CC(C)[N-]C(C)C>>COC=1C=C2C=C(NC2=CC1)/C=C/C1=C(C#N)C=CC=C1 | c1ccc([P+](c2ccccc2)(c2cccc[cH:1]2)[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[C:17]#[N:18])cc1.O=C1NC(=O)c2c1c(I)[cH:9][c:8]1[nH:7][c:6]3[cH:5][cH:4][c:3]([OH:2])[cH:21][c:20]3[c:19]21>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8](/[CH:9]=[CH:10]/[c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[C:17]#[N:18])[cH:19... | N#Cc1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | COc1ccc2[nH]c(/C=C/c3ccccc3C#N)cc2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 76e526426ecd806adac24971ec22abcee22f8ef37d02feb5b78b4790d43dc040 | 298bbddbbad66b4d8f09c0f74d9ca58c3f96284e4a5a7f4c53c37cace7b0e319 | C(=C/c1cc2ccccc2[nH]1)\c1ccccc1 | I-c1:[cH;D2;+0:1]:[c:2]2:[#7;a:3]:[c:4]3:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]:[c:10]:3:[c;H0;D3;+0:11]:2:c2:c:1-C(=O)-N-C-2=O.[c:12]:[c:13](-[CH2;D2;+0:14]-[P+](-c1:[cH;D2;+0:15]:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:16]>>[CH3;D1;+0:15]-[O;H0;D2;+0:8]-[c:7]1:[c:9]:[c:10]2:[cH;D2;+0:11]:[c:2](/[CH;D2;+0:1]=[C... | null | [] | null | null | 5 | HOUR | The 5-methoxy-1H-indole-2-carbaldehyde (1) was reacted with (2-cyanobenzyl)(triphenyl)phosphonium bromide (547) prepared as described in example 136 using the procedure described in example 37, except that the LDA and aldehyde were (sequentially) added at 0° C., the ratio of LDA:aldehyde was 1.55:1 and the reaction tim... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Unsubstituted dicarboximide.Aromatic alcohol | Ether | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HI | null | null | 5 | N#Cc1ccccc1C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1ccc2[nH]c(/C=C/c3ccccc3C#N)cc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2712ded50a36435682981de16c8069c0 | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=[N+]([O-])c1cccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1>>COc1ccc2[nH]c(/C=C/c3cccc([N+](=O)[O-])c3)cc2c1 | [Li+].CC(C)[N-]C(C)C.OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.[Br-].[N+](=O)([O-])C=1C=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC1.[Li+].CC(C)[N-]C(C)C>>COC=1C=C2C=C(NC2=CC1)\C=C\C1=CC(=CC=C1)[N+](=O)[O-] | O=C1NC(=O)c2c1c(I)[cH:9][c:8]1[nH:7][c:6]3[cH:5][cH:4][c:3]([OH:2])[cH:22][c:21]3[c:20]21.c1ccc([P+](c2ccccc2)(c2cccc[cH:1]2)[CH2:10][c:11]2[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8](/[CH:9]=[CH:10]/[c:11]3[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17]... | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=[N+]([O-])c1cccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1 | COc1ccc2[nH]c(/C=C/c3cccc([N+](=O)[O-])c3)cc2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 76e526426ecd806adac24971ec22abcee22f8ef37d02feb5b78b4790d43dc040 | 298bbddbbad66b4d8f09c0f74d9ca58c3f96284e4a5a7f4c53c37cace7b0e319 | C(=C/c1cc2ccccc2[nH]1)\c1ccccc1 | I-c1:[cH;D2;+0:1]:[c:2]2:[#7;a:3]:[c:4]3:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]:[c:10]:3:[c;H0;D3;+0:11]:2:c2:c:1-C(=O)-N-C-2=O.[c:12]:[c:13](-[CH2;D2;+0:14]-[P+](-c1:[cH;D2;+0:15]:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:16]>>[CH3;D1;+0:15]-[O;H0;D2;+0:8]-[c:7]1:[c:9]:[c:10]2:[cH;D2;+0:11]:[c:2](/[CH;D2;+0:1]=[C... | null | [] | null | null | 5 | HOUR | The 5-methoxy-1H-indole-2-carbaldehyde (1) was reacted with (3-nitrobenzyl)(triphenyl)phosphonium bromide using the procedure described in example 37, except that the LDA and aldehyde were sequentially added at 0° C., the ratio of LDA:aldehyde was 1.5:1 and the reaction time was 5 h, to give (after crystallisation from... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Unsubstituted dicarboximide.Aromatic alcohol | Ether | c1ccc2c(c1)nc1ccc3c(c12)CNC3.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HI | null | null | 5 | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=[N+]([O-])c1cccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1>>COc1ccc2[nH]c(/C=C/c3cccc([N+](=O)[O-])c3)cc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fa1cddeabd1848c58bbff604171a8e90 | Cc1cccc([N+](=O)[O-])c1Cl.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>O=[N+]([O-])c1cccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1Cl.[Br-] | ClC1=C(C=CC=C1[N+](=O)[O-])C.C1CC(=O)N(C1=O)Br.CC(C)(C#N)N=NC(C)(C)C#N.[Br-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1[N+](=O)[O-] | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH3:9])[c:29]1[Cl:30].O=C1CCC(=O)N1[Br:31].[P:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][P+:10]([c:11]2[cH:12][cH:13... | Cc1cccc([N+](=O)[O-])c1Cl.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | O=[N+]([O-])c1cccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1Cl.[Br-] | null | null | C(Cl)Cl.C1=CC=CC=C1 | Miscellaneous | OtherReaction | 90798389381727105f8f2fc21b48c935111a22021515f706338ce609a905e694 | 7953bead7af5583757c739601734838d384eb4a189267c5eeec33f580917362a | c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5].[c:6]:[c:7](-[P;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]>>[Br-;H0;D0:1].[c:6]:[c:7](-[P+;H0;D4:8](-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15] | 44 | [{"value": 44.0, "product": "[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Bromination of 2-chloro-3-nitrotoluene with NBS/AIBN, followed by reaction of the crude bromide with triphenylphosphine, using the procedure described in example 102, except that the reaction time for the bromination was 2 h and the displacement reaction was performed at 70° C. for 1 d, gave the phosphonium salt (554) ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | null | C1CCNC1 | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl.C1=CC=CC=C1 | null | 2 | Cc1cccc([N+](=O)[O-])c1Cl.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C(Cl)Cl.C1=CC=CC=C1>O=[N+]([O-])c1cccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1Cl.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0a3ddf2f18b44842bcac40e66ad962e1 | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=[N+]([O-])c1cccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1Cl>>COc1ccc2[nH]c(/C=C/c3cccc([N+](=O)[O-])c3Cl)cc2c1 | [Li+].CC(C)[N-]C(C)C.OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C1[N+](=O)[O-].[Li+].CC(C)[N-]C(C)C>>ClC1=C(C=CC=C1[N+](=O)[O-])/C=C/C=1NC2=CC=C(C=C2C1)OC | O=C1NC(=O)c2c1c(I)[cH:9][c:8]1[nH:7][c:6]3[cH:5][cH:4][c:3]([OH:2])[cH:23][c:22]3[c:21]21.c1ccc([P+](c2ccccc2)(c2cccc[cH:1]2)[CH2:10][c:11]2[cH:12][cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[c:19]2[Cl:20])cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8](/[CH:9]=[CH:10]/[c:11]3[cH:12][cH:13][cH:14][c:15]([N+:16](=... | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=[N+]([O-])c1cccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1Cl | COc1ccc2[nH]c(/C=C/c3cccc([N+](=O)[O-])c3Cl)cc2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 76e526426ecd806adac24971ec22abcee22f8ef37d02feb5b78b4790d43dc040 | 298bbddbbad66b4d8f09c0f74d9ca58c3f96284e4a5a7f4c53c37cace7b0e319 | C(=C/c1cc2ccccc2[nH]1)\c1ccccc1 | I-c1:[cH;D2;+0:1]:[c:2]2:[#7;a:3]:[c:4]3:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]:[c:10]:3:[c;H0;D3;+0:11]:2:c2:c:1-C(=O)-N-C-2=O.[c:12]:[c:13](-[CH2;D2;+0:14]-[P+](-c1:[cH;D2;+0:15]:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:16]>>[CH3;D1;+0:15]-[O;H0;D2;+0:8]-[c:7]1:[c:9]:[c:10]2:[cH;D2;+0:11]:[c:2](/[CH;D2;+0:1]=[C... | null | [] | null | null | 5 | HOUR | The 5-methoxy-1H-indole-2-carbaldehyde (1) was reacted with (2-chloro-3-nitrobenzyl)(triphenyl)phosphonium bromide (554) preared as described in example 143 using the procedure described in example 37, except that the LDA and aldehyde were (sequentially) added at 0° C., the ratio of LDA:aldehyde was 1.5:1 and the react... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Unsubstituted dicarboximide.Aromatic alcohol | Ether | c1ccc2c(c1)nc1ccc3c(c12)CNC3.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HI | null | null | 5 | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=[N+]([O-])c1cccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1Cl>>COc1ccc2[nH]c(/C=C/c3cccc([N+](=O)[O-])c3Cl)cc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b77c515b4e7647afacc2b1635151178a | Cc1ccc([N+](=O)[O-])cc1Cl.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>O=[N+]([O-])c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1.[Br-] | ClC1=C(C=CC(=C1)[N+](=O)[O-])C.C1CC(=O)N(C1=O)Br.CC(C)(C#N)N=NC(C)(C)C#N.[Br-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC(=C1)[N+](=O)[O-] | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([CH3:8])[c:28]([Cl:29])[cH:30]1.O=C1CCC(=O)N1[Br:31].[P:9]([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][P+:9]([c:10]2[cH:11][cH:12][cH:... | Cc1ccc([N+](=O)[O-])cc1Cl.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | O=[N+]([O-])c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1.[Br-] | null | null | C1=CC=CC=C1 | Miscellaneous | OtherReaction | 90798389381727105f8f2fc21b48c935111a22021515f706338ce609a905e694 | 7953bead7af5583757c739601734838d384eb4a189267c5eeec33f580917362a | c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5].[c:6]:[c:7](-[P;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]>>[Br-;H0;D0:1].[c:6]:[c:7](-[P+;H0;D4:8](-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15] | 34 | [{"value": 34.0, "product": "[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC(=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Bromination of 2-chloro-4-nitrotoluene with NBS/AIBN, followed by reaction of the crude bromide with triphenylphosphine, using the procedure described in example 102, except that the reaction time for the bromination was 24 h and the displacement reaction was performed at 20° C. for 7 d, gave the crude phosphonium salt... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | null | C1CCNC1 | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C1=CC=CC=C1 | null | 24 | Cc1ccc([N+](=O)[O-])cc1Cl.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C1=CC=CC=C1>O=[N+]([O-])c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d71f862c74a843f7a18c5255b186b546 | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=[N+]([O-])c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1>>COc1ccc2[nH]c(/C=C/c3ccc([N+](=O)[O-])cc3Cl)cc2c1 | [Li+].CC(C)[N-]C(C)C.OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC(=C1)[N+](=O)[O-].[Li+].CC(C)[N-]C(C)C>>ClC1=C(C=CC(=C1)[N+](=O)[O-])/C=C/C=1NC2=CC=C(C=C2C1)OC | O=C1NC(=O)c2c1c(I)[cH:9][c:8]1[nH:7][c:6]3[cH:5][cH:4][c:3]([OH:2])[cH:23][c:22]3[c:21]21.c1ccc([P+](c2ccccc2)(c2cccc[cH:1]2)[CH2:10][c:11]2[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][c:19]2[Cl:20])cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8](/[CH:9]=[CH:10]/[c:11]3[cH:12][cH:13][c:14]([N+:15](=[O:16])... | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=[N+]([O-])c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1 | COc1ccc2[nH]c(/C=C/c3ccc([N+](=O)[O-])cc3Cl)cc2c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 76e526426ecd806adac24971ec22abcee22f8ef37d02feb5b78b4790d43dc040 | 298bbddbbad66b4d8f09c0f74d9ca58c3f96284e4a5a7f4c53c37cace7b0e319 | C(=C/c1cc2ccccc2[nH]1)\c1ccccc1 | I-c1:[cH;D2;+0:1]:[c:2]2:[#7;a:3]:[c:4]3:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]:[c:10]:3:[c;H0;D3;+0:11]:2:c2:c:1-C(=O)-N-C-2=O.[c:12]:[c:13](-[CH2;D2;+0:14]-[P+](-c1:[cH;D2;+0:15]:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:16]>>[CH3;D1;+0:15]-[O;H0;D2;+0:8]-[c:7]1:[c:9]:[c:10]2:[cH;D2;+0:11]:[c:2](/[CH;D2;+0:1]=[C... | null | [] | null | null | 5 | HOUR | The 5-methoxy-1H-indole-2-carbaldehyde (1) was reacted with (2-chloro-4-nitrobenzyl)(triphenyl)phosphonium bromide (559) prepared as described in example 148 using the procedure described in example 37, except that the LDA and aldehyde were (sequentially) added at 0° C., the ratio of LDA:aldehyde was 1.5:1 and the reac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Unsubstituted dicarboximide.Aromatic alcohol | Ether | c1ccc2c(c1)nc1ccc3c(c12)CNC3.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HI | null | null | 5 | O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21.O=[N+]([O-])c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1>>COc1ccc2[nH]c(/C=C/c3ccc([N+](=O)[O-])cc3Cl)cc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5ff65fcfe3074652ab6aafbfe9be302d | Br.O=[N+]([O-])c1ccc(Cl)c(CO)c1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>O=[N+]([O-])c1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1.[Br-] | ClC1=C(C=C(C=C1)[N+](=O)[O-])CO.Br.[Br-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C(C=C1)[N+](=O)[O-] | [BrH:31].O[CH2:10][c:9]1[c:7]([Cl:8])[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:30]1.[P:11]([c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)([c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([Cl:8])[c:9]([CH2:10][P+:11]([c:12]2[cH:13][cH:14]... | Br.O=[N+]([O-])c1ccc(Cl)c(CO)c1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | O=[N+]([O-])c1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1.[Br-] | null | null | C(C)(=O)O.C(Cl)Cl.C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | bbb792e2dbaac6137f4ab4b2ad2edf8b90c54de5f7db3b319a5444b78b4405dc | 5700379a096deb40e2dc50b293f55a01cfe36aa58cf97bdfa006d0b7ff21038e | c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[BrH;D0;+0:5].[c:6]:[c:7](-[P;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]>>[Br-;H0;D0:5].[c:6]:[c:7](-[P+;H0;D4:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15] | 63 | [{"value": 63.0, "product": "[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Bromination of (2-chloro-5-nitrophenyl)methanol with 30% HBr in acetic acid, followed by reaction of the crude bromide with triphenylphosphine, using the procedure described in example 112, gave the phosphonium salt (564) (63%) as a white solid, mp (CH2Cl2/benzene) 239–243° C. 1H NMR (CDCl3) δ 8.22 (br s, 1H), 8.07 (br... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C(Cl)Cl.C1=CC=CC=C1 | null | null | Br.O=[N+]([O-])c1ccc(Cl)c(CO)c1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C(C)(=O)O.C(Cl)Cl.C1=CC=CC=C1>O=[N+]([O-])c1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b0cc435ca11b4dacb9b6522a9e461fa6 | Br.COc1ccc(CO)c(Cl)c1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>COc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1.[Br-] | ClC1=C(C=CC(=C1)OC)CO.Br.[Br-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC(=C1)OC | [BrH:30].O[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:29][c:27]1[Cl:28].[P:8]([c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][P+:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)([c:15]2[cH:... | Br.COc1ccc(CO)c(Cl)c1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | COc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1.[Br-] | null | null | C(C)(=O)O.C(Cl)Cl.C1=CC=CC=C1 | Functional Group Interconversion | OtherReaction | bbb792e2dbaac6137f4ab4b2ad2edf8b90c54de5f7db3b319a5444b78b4405dc | 5700379a096deb40e2dc50b293f55a01cfe36aa58cf97bdfa006d0b7ff21038e | c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[BrH;D0;+0:5].[c:6]:[c:7](-[P;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]>>[Br-;H0;D0:5].[c:6]:[c:7](-[P+;H0;D4:8](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15] | 100 | [{"value": 100.0, "product": "[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC(=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Bromination of (2-chloro-4-methoxyphenyl)methanol with 30% HBr in acetic acid, followed by reaction of the crude bromide with triphenylphosphine, using the procedure described in example 112, except that the reaction time for the bromination was 4 h and the reaction time for the displacement was 28 h, gave the phosphon... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C(Cl)Cl.C1=CC=CC=C1 | null | 4 | Br.COc1ccc(CO)c(Cl)c1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C(C)(=O)O.C(Cl)Cl.C1=CC=CC=C1>COc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7ccdd8dbcf034a15acfdf0ca50cc01a9 | COc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1ccc(/C=C/c2cc3cc(OC)ccc3[nH]2)c(Cl)c1 | [Li+].CC(C)[N-]C(C)C.OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=CC(=C1)OC.[Li+].CC(C)[N-]C(C)C>>ClC1=C(C=CC(=C1)OC)/C=C/C=1NC2=CC=C(C=C2C1)OC | c1ccc([P+](c2ccccc2)(c2cccc[cH:15]2)[CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22][c:20]2[Cl:21])cc1.O=C1NC(=O)c2c1c(I)[cH:8][c:9]1[c:10]2[c:11]2[cH:12][c:13]([OH:14])[cH:16][cH:17][c:18]2[nH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[CH:8]/[c:9]2[cH:10][c:11]3[cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17][c:... | COc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | COc1ccc(/C=C/c2cc3cc(OC)ccc3[nH]2)c(Cl)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 76e526426ecd806adac24971ec22abcee22f8ef37d02feb5b78b4790d43dc040 | 298bbddbbad66b4d8f09c0f74d9ca58c3f96284e4a5a7f4c53c37cace7b0e319 | C(=C/c1cc2ccccc2[nH]1)\c1ccccc1 | I-c1:[cH;D2;+0:1]:[c:2]2:[#7;a:3]:[c:4]3:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]:[c:10]:3:[c;H0;D3;+0:11]:2:c2:c:1-C(=O)-N-C-2=O.[c:12]:[c:13](-[CH2;D2;+0:14]-[P+](-c1:[cH;D2;+0:15]:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:16]>>[CH3;D1;+0:15]-[O;H0;D2;+0:8]-[c:7]1:[c:9]:[c:10]2:[cH;D2;+0:11]:[c:2](/[CH;D2;+0:1]=[C... | null | [] | null | null | 5 | HOUR | The 5-methoxy-1H-indole-2-carbaldehyde (1) was reacted with (2-chloro-4-methoxybenzyl)(triphenyl)phosphonium bromide (574) prepared as described in example 162 using the procedure described in example 37, except that the LDA and aldehyde were sequentially added at 0° C., the ratio of LDA:aldehyde was 1.5:1 and the reac... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Unsubstituted dicarboximide.Aromatic alcohol | Ether | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HI | null | null | 5 | COc1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c(Cl)c1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1ccc(/C=C/c2cc3cc(OC)ccc3[nH]2)c(Cl)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bfdc92081d604501937dbab0c74fb0e9 | COc1ccc(Cl)c(C)c1.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>COc1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1.[Br-] | ClC1=C(C=C(C=C1)OC)C.C1CC(=O)N(C1=O)Br.CC(C)(C#N)N=NC(C)(C)C#N.[Br-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[c:8]([CH3:9])[cH:29]1.O=C1CCC(=O)N1[Br:30].[P:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)([c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1)[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[c:8]([CH2:9][P+:10]([c:11]2[cH:12][cH:13][cH:14]... | COc1ccc(Cl)c(C)c1.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | COc1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1.[Br-] | null | null | C(Cl)Cl.C1=CC=CC=C1 | Miscellaneous | OtherReaction | 90798389381727105f8f2fc21b48c935111a22021515f706338ce609a905e694 | 7953bead7af5583757c739601734838d384eb4a189267c5eeec33f580917362a | c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5].[c:6]:[c:7](-[P;H0;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15]>>[Br-;H0;D0:1].[c:6]:[c:7](-[P+;H0;D4:8](-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5])(-[c:9](:[c:10]):[c:11])-[c:12](:[c:13]):[c:14]):[c:15] | 76 | [{"value": 76.0, "product": "[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Bromination of 1-chloro-4-methoxy-2-methylbenzene with NBS/AIBN, followed by reaction of the crude bromide with triphenylphosphine, using the procedure described in example 102, except that the reaction time for the bromination was 4 h, gave the phosphonium salt (578) (76%) as a light brown solid, mp (CH2Cl2/benzene) 1... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | null | C1CCNC1 | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl.C1=CC=CC=C1 | null | 4 | COc1ccc(Cl)c(C)c1.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1>C(Cl)Cl.C1=CC=CC=C1>COc1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1.[Br-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-75df05aa2dc442c2a14c9e3dbed3c708 | COc1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1ccc(Cl)c(/C=C/c2cc3cc(OC)ccc3[nH]2)c1 | [Li+].CC(C)[N-]C(C)C.OC1=CC=2C=3C4=C(C(=CC3NC2C=C1)I)C(NC4=O)=O.[Br-].ClC1=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C(C=C1)OC.[Li+].CC(C)[N-]C(C)C>>ClC1=C(C=C(C=C1)OC)/C=C/C=1NC2=CC=C(C=C2C1)OC | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:9][c:8]2[c:6]([Cl:7])[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:22]2)cc1.O=C1NC(=O)c2c1c(I)[cH:10][c:11]1[c:12]2[c:13]2[cH:14][c:15]([OH:16])[cH:18][cH:19][c:20]2[nH:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([Cl:7])[c:8](/[CH:9]=[CH:10]/[c:11]2[cH:12][c:13]3[cH:14][c:15]([O:16][CH3:17])[cH:18... | COc1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21 | COc1ccc(Cl)c(/C=C/c2cc3cc(OC)ccc3[nH]2)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 76e526426ecd806adac24971ec22abcee22f8ef37d02feb5b78b4790d43dc040 | 298bbddbbad66b4d8f09c0f74d9ca58c3f96284e4a5a7f4c53c37cace7b0e319 | C(=C/c1cc2ccccc2[nH]1)\c1ccccc1 | I-c1:[cH;D2;+0:1]:[c:2]2:[#7;a:3]:[c:4]3:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]:[c:10]:3:[c;H0;D3;+0:11]:2:c2:c:1-C(=O)-N-C-2=O.[c:12]:[c:13](-[CH2;D2;+0:14]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:15]>>[C;D1;H3:16]-[O;H0;D2;+0:8]-[c:7]1:[c:9]:[c:10]2:[cH;D2;+0:11]:[c:2](/[CH;D2;+0:1]=[CH;D2;+0:14]/[c... | null | [] | null | null | 5 | HOUR | The 5-methoxy-1H-indole-2-carbaldehyde (1) was reacted with (2-chloro-5-methoxybenzyl)(triphenyl)phosphonium bromide (578) prepared as described in example 166 using the procedure described in example 37, except that the LDA and aldehyde were (sequentially) added at 0° C., the ratio of LDA:aldehyde was 1.5:1 and the re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Unsubstituted dicarboximide.Aromatic alcohol | Ether | c1ccccc1.c1ccccc1.c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HI | null | null | 5 | COc1ccc(Cl)c(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)c1.O=C1NC(=O)c2c1c(I)cc1[nH]c3ccc(O)cc3c21>>COc1ccc(Cl)c(/C=C/c2cc3cc(OC)ccc3[nH]2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0f71807f4508467783c850c345328123 | CNC.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr>>CN(C)CCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O | BrCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O.Cl.C([O-])([O-])=O.[K+].[K+].CNC>>CN(CCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O)C | [CH3:1][NH:2][CH3:3].Br[CH2:4][CH2:5][CH2:6][n:7]1[c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:13][c:14]2[c:15]2[c:16]3[c:17]([c:18](-[c:19]4[cH:20][cH:21][cH:22][cH:23][cH:24]4)[cH:25][c:26]12)[C:27](=[O:28])[NH:29][C:30]3=[O:31]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][n:7]1[c:8]2[cH:9][cH:10][c:11]([OH:12])[cH:13][c:14]... | CNC.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr | CN(C)CCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O | null | null | CC(=O)N(C)C.O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[NH;D2;+0:5]-[C;D1;H3:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:5](-[C;D1;H3:4])-[C;D1;H3:6] | 47 | [{"value": 47.0, "product": "CN(CCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O)C", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 18 | HOUR | To a solution of bromide (204) prepared as described in example 173 (0.12 g, 0.27 mmol) in dimethylacetamide (4 mL) was added the amine, dimethylamine (25 mol eq., 0.85 mL in this case as an 40% aqueous solution). The reaction vessel was sealed and heated at 80° C. with stirring for 18 h, before being diluted with wate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | HBr | CC(=O)N(C)C.O | 80 | 18 | CNC.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr>CC(=O)N(C)C.O>CN(C)CCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c269c01594444c85b9e8d70f31ea4028 | CNC.CS(=O)(=O)OCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O>>CN(C)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O | CS(=O)(=O)OCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O.CNC>>CN(CCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O)C | [CH3:1][NH:2][CH3:3].CS(=O)(=O)O[CH2:4][CH2:5][n:6]1[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]2[c:14]2[c:15]3[c:16]([c:17](-[c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[cH:24][c:25]12)[C:26](=[O:27])[NH:28][C:29]3=[O:30]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][n:6]1[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]2[c:14]... | CNC.CS(=O)(=O)OCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O | CN(C)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#7;a:3].[C;D1;H3:4]-[NH;D2;+0:5]-[C;D1;H3:6]>>[#7;a:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:5](-[C;D1;H3:4])-[C;D1;H3:6] | 48 | [{"value": 48.0, "product": "CN(CCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Mesylate (205) prepared as described in example 174 (70 mg, 0.16 mmol) was reacted with aqueous dimethylamine solution according to the procedure described in example 179 to give amine (209) (30 mg, 48%) as a yellow powder, mp 283–286° C. 1H NMR δ [(CD3)2SO] 11.05 (br s, 1H), 9.33 (s, 1H), 8.41 (d, J=2.4 Hz, 1H), 7.77 ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | MsOH.HO- | null | null | null | CNC.CS(=O)(=O)OCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O>>CN(C)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d4de17759f9b43b7a5dcf2c935b7db3d | C1COCCN1.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr>>O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCN1CCOCC1 | BrCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O.N1CCOCC1>>OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCCN1CCOCC1)C1=CC=CC=C1)C(NC4=O)=O | [NH:29]1[CH2:30][CH2:31][O:32][CH2:33][CH2:34]1.Br[CH2:28][CH2:27][CH2:26][n:25]1[c:16]2[cH:15][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:7]3[c:6]([c:17]2[c:18]2[cH:19][c:20]([OH:21])[cH:22][cH:23][c:24]21)[C:4](=[O:5])[NH:3][C:2]3=[O:1]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][... | C1COCCN1.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCN1CCOCC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2bad30dcdb0a20edb8ce877f072b133eedfd870621da393ec393128bfee00977 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2ccccc2n1CCCN1CCOCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#8:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#8:4]-[C:9]-[C:8]-1 | 72 | [{"value": 72.0, "product": "OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCCN1CCOCC1)C1=CC=CC=C1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Bromide (204) (0.01 g, 0.22 mmol) prepared as described in example 173 was reacted with morpholine according to the procedure described in example 179 to give amine (210) (73 mg, 72%) as a yellow powder, mp 252–255° C. 1H NMR δ [(CD3)2SO] 11.04 (br s, 1H), 9.33 (s, 1H), 8.41 (d, J=2.5 Hz, 1H), 7.81 (s, 1H), 7.62 (m, 2H... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1.C1NCc2c1ccc1nc3ccccc3c21 | HBr | null | null | null | C1COCCN1.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr>>O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCN1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d641bce625f5461193f6ee418249272a | C1COCCN1.CS(=O)(=O)OCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O>>O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCN1CCOCC1 | CS(=O)(=O)OCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O.N1CCOCC1>>OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCN1CCOCC1)C1=CC=CC=C1)C(NC4=O)=O | [NH:28]1[CH2:29][CH2:30][O:31][CH2:32][CH2:33]1.CS(=O)(=O)O[CH2:27][CH2:26][n:25]1[c:16]2[cH:15][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:7]3[c:6]([c:17]2[c:18]2[cH:19][c:20]([OH:21])[cH:22][cH:23][c:24]21)[C:4](=[O:5])[NH:3][C:2]3=[O:1]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11]... | C1COCCN1.CS(=O)(=O)OCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCN1CCOCC1 | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | d65566d5f2049ef4dc70d5c480ea5af77518b25af8327af37e9d6d45c6baf558 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2ccccc2n1CCN1CCOCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#7;a:3].[#8:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[#7;a:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#8:4]-[C:9]-[C:8]-1 | 75 | [{"value": 75.0, "product": "OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCN1CCOCC1)C1=CC=CC=C1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Mesylate (205) (70 mg, 0.16 mmol) prepared as described in example 174 was reacted with morpholine according to the procedure described in example 179 to give amine (211) (53 mg, 75%) as a yellow powder, mp 260–262° C. 1H NMR □ [(CD3)2SO) 1H NMR δ [(CD3)2SO] 11.04 (br s, 1H), 9.33 (s, 1H), 8.40 (d, J=2.5 Hz, 1H), 7.78 ... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1.C1NCc2c1ccc1nc3ccccc3c21 | MsOH.HO- | null | null | null | C1COCCN1.CS(=O)(=O)OCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O>>O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCN1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-99f392333f6a419c98f8fcb3e8e152c6 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr.c1c[nH]cn1>>O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCn1ccnc1 | BrCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O.N1C=NC=C1>>OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCCN1C=NC=C1)C1=CC=CC=C1)C(NC4=O)=O | Br[CH2:28][CH2:27][CH2:26][n:25]1[c:16]2[cH:15][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:7]3[c:6]([c:17]2[c:18]2[cH:19][c:20]([OH:21])[cH:22][cH:23][c:24]21)[C:4](=[O:5])[NH:3][C:2]3=[O:1].[nH:29]1[cH:30][cH:31][n:32][cH:33]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][cH:12][cH:1... | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr.c1c[nH]cn1 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCn1ccnc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2ccccc2n1CCCn1ccnc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]1:[c:5]:[c:6]:[nH;D2;+0:7]:[c:8]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[#7;a:4]:[c:8]:1 | 53 | [{"value": 53.0, "product": "OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCCN1C=NC=C1)C1=CC=CC=C1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Bromide (204) (80 mg, 0.18 mmol) prepared as described in example 173 was reacted with imidazole according to the procedure described in example 179 to give amine (212) (41 mg, 53%) as a yellow powder, mp 309–311° C. 1H NMR δ [(CD3)2SO] 11.06 (s, 1H), 9.36 (s, 1H), 8.40 (d, J=2.3 Hz, 1H), 7.69 (s, 1H), 7.64 (m, 3H), 7.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1.C1NCc2c1ccc1nc3ccccc3c21 | HBr | null | null | null | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr.c1c[nH]cn1>>O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCn1ccnc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-30442443bd474eb2884df4fb92dcbd48 | CS(=O)(=O)OCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O.c1c[nH]cn1>>O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCn1ccnc1 | CS(=O)(=O)OCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O.N1C=NC=C1>>OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCN1C=NC=C1)C1=CC=CC=C1)C(NC4=O)=O | CS(=O)(=O)O[CH2:27][CH2:26][n:25]1[c:16]2[cH:15][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:7]3[c:6]([c:17]2[c:18]2[cH:19][c:20]([OH:21])[cH:22][cH:23][c:24]21)[C:4](=[O:5])[NH:3][C:2]3=[O:1].[nH:28]1[cH:29][cH:30][n:31][cH:32]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][cH:12][cH:... | CS(=O)(=O)OCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O.c1c[nH]cn1 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCn1ccnc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c442140b096c54ef671e11ca8ca216d6e6322c408fe778838cc14d7f651c7f7d | 0b4f3c8c88df0a792d0db7d59004d7fe5681a61dd48ef2449ddca2d636f76ada | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2ccccc2n1CCn1ccnc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#7;a:3].[#7;a:4]1:[c:5]:[c:6]:[nH;D2;+0:7]:[c:8]:1>>[#7;a:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[#7;a:4]:[c:8]:1 | 50 | [{"value": 50.0, "product": "OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCN1C=NC=C1)C1=CC=CC=C1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Mesylate (205) (70 mg, 0.16 mmol) prepared as described in example 174 was reacted with imidazole according to the procedure described in example 179 to give amine (213) (34 mg, 50%) as a yellow powder, mp>345° C. 1H NMR δ [(CD3)2SO] 11.05 (br s, 1H), 9.34 (s, 1H), 8.39 (d, J=2.4 Hz, 1H), 7.59 (m, 2H), 7.45 (m, 5H), 7.... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1.C1NCc2c1ccc1nc3ccccc3c21 | MsOH.HO- | null | null | null | CS(=O)(=O)OCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O.c1c[nH]cn1>>O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCn1ccnc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bcc8870612fe4c60b84f7a1252511146 | CN.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr>>CNCCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O | BrCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O.CN>>OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCCNC)C1=CC=CC=C1)C(NC4=O)=O | [CH3:1][NH2:2].Br[CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]2[c:14]2[c:15]3[c:16]([c:17](-[c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[cH:24][c:25]12)[C:26](=[O:27])[NH:28][C:29]3=[O:30]>>[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]2[c:14]2[c:15]3[... | CN.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr | CNCCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[NH2;D1;+0:5]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:5]-[C;D1;H3:4] | 61.2 | [{"value": 61.0, "product": "OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCCNC)C1=CC=CC=C1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.2, "product": "OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCCNC)C1=CC=CC=C1)C(NC4=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Bromide (204) (40 mg, 0.09 mmol) prepared as described in example 173 was reacted with aqueous methylamine solution (10 mol equiv.) according to the procedure described in example 179 except that the reaction was performed in dimethylsulfoxide at room temperature for 3 h, to give amine (214) (22 mg, 61%) as an orange/y... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | HBr | CS(=O)C | null | null | CN.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr>CS(=O)C>CNCCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2a3230ac66084754a1ba89fe21f7b805 | C1CNCCN1.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr>>O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCN1CCNCC1 | BrCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O.N1CCNCC1>>OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCCN1CCNCC1)C1=CC=CC=C1)C(NC4=O)=O | [NH:29]1[CH2:30][CH2:31][NH:32][CH2:33][CH2:34]1.Br[CH2:28][CH2:27][CH2:26][n:25]1[c:16]2[cH:15][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:7]3[c:6]([c:17]2[c:18]2[cH:19][c:20]([OH:21])[cH:22][cH:23][c:24]21)[C:4](=[O:5])[NH:3][C:2]3=[O:1]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11]... | C1CNCCN1.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCN1CCNCC1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 61ec49e5207aa33ebff7094bb66b1d997d4af14524931a8b3643ef7a94219a9a | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2ccccc2n1CCCN1CCNCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 55 | [{"value": 55.0, "product": "OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCCN1CCNCC1)C1=CC=CC=C1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | Bromide (204) (70 mg, 0.16 mmol) prepared as described in example 173 was reacted with piperazine according to The procedure described in example 179 except that the reaction was performed at room temperature for 20 h, to give amine (215) (40 mg, 55%) as a yellow powder, mp 178–183° C. 1H NMR δ [(CD3)2SO] 11.0 (br s, 1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCCN1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1.C1NCc2c1ccc1nc3ccccc3c21 | HBr | null | null | 20 | C1CNCCN1.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr>>O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCN1CCNCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aece01f510ab41f1a3cba2126cfe5d57 | Nc1ccccc1.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr>>O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCNc1ccccc1 | BrCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O.NC1=CC=CC=C1>>N(C1=CC=CC=C1)CCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O | [NH2:29][c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1.Br[CH2:28][CH2:27][CH2:26][n:25]1[c:16]2[cH:15][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[c:7]3[c:6]([c:17]2[c:18]2[cH:19][c:20]([OH:21])[cH:22][cH:23][c:24]21)[C:4](=[O:5])[NH:3][C:2]3=[O:1]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:... | Nc1ccccc1.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCNc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2ccccc2n1CCCNc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 38 | [{"value": 38.0, "product": "N(C1=CC=CC=C1)CCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | Bromide (204) (75 mg, 0.17 mmol) prepared as described in example 173 was reacted with aniline according to the procedure described in example 179 except that the reaction was performed at room temperature for 20 h, to give aniline (217) (30 mg, 38%) as a yellow powder, mp 240° C. (dec). 1H NMR δ [(CD3)2SO] 11.04 (br s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.C1NCc2c1ccc1nc3ccccc3c21 | HBr | null | null | 20 | Nc1ccccc1.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCBr>>O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCNc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3891d5b333be4fc9af36bb80c85af3c7 | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCCBr.C[C@@H]1CNC[C@H](C)N1>>COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCCN1C[C@@H](C)N[C@@H](C)C1 | BrCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1OC)Cl)C(NC3=O)=O)O.C[C@@H]1N[C@@H](CNC1)C>>ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCCN2C[C@H](N[C@H](C2)C)C | Br[CH2:31][CH2:30][CH2:29][n:28]1[c:12]2[cH:11][c:10](-[c:9]3[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]3[Cl:8])[c:15]3[c:14]([c:13]2[c:21]2[cH:22][c:23]([OH:24])[cH:25][cH:26][c:27]21)[C:19](=[O:20])[NH:18][C:16]3=[O:17].[NH:32]1[CH2:33][C@@H:34]([CH3:35])[NH:36][C@@H:37]([CH3:38])[CH2:39]1>>[CH3:1][O:2][c:3]1[cH:4][cH... | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCCBr.C[C@@H]1CNC[C@H](C)N1 | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCCN1C[C@@H](C)N[C@@H](C)C1 | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 61ec49e5207aa33ebff7094bb66b1d997d4af14524931a8b3643ef7a94219a9a | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2ccccc2n1CCCN1CCNCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | 98 | [{"value": 98.0, "product": "ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCCN2C[C@H](N[C@H](C2)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | Bromide (207) (60 mg, 0.12 mmol), prepared as described in example 176, was reacted with cis-2,6-dimethylpiperazine according to the procedure described in example 179 except that the reaction was performed at room temperature for 20 h, to give amine (218) (63 mg, 98%) as a yellow powder, mp 199–202° C. 1H NMR δ [(CD3)... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCCN1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1.C1NCc2c1ccc1nc3ccccc3c21 | HBr | null | null | 20 | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCCBr.C[C@@H]1CNC[C@H](C)N1>>COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCCN1C[C@@H](C)N[C@@H](C)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6296394591cb4d9196dd59a65c6dc03f | CS(=O)(=O)OCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O.Sc1ccccc1>>O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCSc1ccccc1 | CS(=O)(=O)OCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)Cl)C(NC3=O)=O)O.C1(=CC=CC=C1)S.C(C)N(CC)CC>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCSC2=CC=CC=C2 | CS(=O)(=O)O[CH2:28][CH2:27][n:26]1[c:17]2[cH:16][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[Cl:15])[c:7]3[c:6]([c:18]2[c:19]2[cH:20][c:21]([OH:22])[cH:23][cH:24][c:25]21)[C:4](=[O:5])[NH:3][C:2]3=[O:1].[SH:29][c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:1... | CS(=O)(=O)OCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O.Sc1ccccc1 | O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCSc1ccccc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | bb86271f960c642587dc900180f99bfb3d3eab3ca39b11b3cb70560d94f407f0 | 16472cd174cc2da3287c614705959a9f9d18ac963bc8ef0c26feb5dd489d747b | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2ccccc2n1CCSc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[#7;a:3].[SH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7;a:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 27 | [{"value": 27.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCSC2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | Mesylate (229) (55 mg, 0.11 mmol) prepared as decribed in example 171 was reacted with excess thiophenol (0.10 mL) according to the procedure described in example 179, except that triethylamine (2.0 mL) was added and the reaction was heated at 110° C. for 4 days. Addition of water was followed by extracted of the compo... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic thiol | Monosulfide | null | null | c1ccccc1.c1ccccc1.C1NCc2c1ccc1nc3ccccc3c21 | MsOH.HO- | O | 110 | null | CS(=O)(=O)OCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O.Sc1ccccc1>O>O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCSc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b89c3cc6000840ceb21cafb05db13925 | Nc1ccccc1C(=O)O.O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCBr>>O=C(O)c1ccccc1NCCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | BrCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)Cl)C(NC3=O)=O)O.C1=CC=C(C(=C1)C(=O)O)N>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCCNC2=C(C(=O)O)C=CC=C2 | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[NH2:10].Br[CH2:11][CH2:12][CH2:13][n:14]1[c:15]2[cH:16][cH:17][c:18]([OH:19])[cH:20][c:21]2[c:22]2[c:23]3[c:24]([c:25](-[c:26]4[cH:27][cH:28][cH:29][cH:30][c:31]4[Cl:32])[cH:33][c:34]12)[C:35](=[O:36])[NH:37][C:38]3=[O:39]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH... | Nc1ccccc1C(=O)O.O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCBr | O=C(O)c1ccccc1NCCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2ccccc2n1CCCNc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10] | 88 | [{"value": 88.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCCNC2=C(C(=O)O)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of the bromide (58) prepared as described in example 172 with o-anthranilic acid using the procedure described in example 179 gave the aniline (60) (88%), mp 261–263° C. 1H NMR δ [(CD3)2SO] 11.05 (s, 1H), 9.38 (s, 1H), 8.39 (d, J=2.4 Hz, 1H), 7.76 (m, 1H), 7.75 (s, 1H), 7.59 (d, J=8.7 Hz, 1H), 7.55 (m, 1H), 7.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | HBr | null | null | null | Nc1ccccc1C(=O)O.O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCBr>>O=C(O)c1ccccc1NCCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-abff0e57043e4cab848989dfd590d22d | O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCBr>>CSCCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | BrCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)Cl)C(NC3=O)=O)O.[Li].[Li]SC>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCCSC | Br[CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]2[c:14]2[c:15]3[c:16]([c:17](-[c:18]4[cH:19][cH:20][cH:21][cH:22][c:23]4[Cl:24])[cH:25][c:26]12)[C:27](=[O:28])[NH:29][C:30]3=[O:31]>>[CH3:1][S:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]2[c:14]2[c:15]3[c:16]([c:1... | O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCBr | CSCCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | null | null | O.O1CCOCC1 | Miscellaneous | OtherReaction | c7f6703d8c9a47e72372c222cbd53ce8b0f05c02a135956dea2f6ecbca239ce6 | acbc727a20407483543a5245cd99740ae3639831d576fa39047899f0e1fe81f3 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[#16:4]-[C;D1;H3:5] | null | [] | null | null | 9 | HOUR | A mixture of the bromide (58) (60.0 mg, 0.124 mmol) prepared as described in example 172 and lithium thiomercaptide (13 mg, 0.2481 mmol) in p-dioxane (5 mL) was refluxed for 16 h. A further 10 mg of LiSMe was added and refluxing was continued for a further 9 h. The mixture was diluted with water, extracted with ethyl a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Monosulfide | null | null | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | Br- | O.O1CCOCC1 | null | 9 | O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCBr>O.O1CCOCC1>CSCCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d5151d0c90e84864901a4cd4c077061f | O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCBr.Sc1ccccc1>>O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCSc1ccccc1 | O.BrCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)Cl)C(NC3=O)=O)O.C1(=CC=CC=C1)S.C(C)N(CC)CC>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCCSC2=CC=CC=C2 | Br[CH2:29][CH2:28][CH2:27][n:26]1[c:17]2[cH:16][c:8](-[c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[Cl:15])[c:7]3[c:6]([c:18]2[c:19]2[cH:20][c:21]([OH:22])[cH:23][cH:24][c:25]21)[C:4](=[O:5])[NH:3][C:2]3=[O:1].[SH:30][c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10... | O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCBr.Sc1ccccc1 | O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCSc1ccccc1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2ccccc2n1CCCSc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[SH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A solution of the bromide (58) (41 mg, 0.085 mmol) prepared as described in example 172, thiophenol (9.5 μL, 0.093 mmol) and triethylamine (0.25 mL, 3.40 mmol) in p-dioxane (1.5 mL) was refluxed for 16 h. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried, the drying agent was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccccc1.c1ccccc1.C1NCc2c1ccc1nc3ccccc3c21 | HBr | O1CCOCC1 | null | null | O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCBr.Sc1ccccc1>O1CCOCC1>O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCSc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2074e4d1b268405a81592841c2097642 | CO.C[O-].O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCBr>>COCCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)OC3=O | Cl.BrCCCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)Cl)C(NC3=O)=O)O.CO.C[O-].[Na+]>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(OC2=O)=O)O)CCCOC | C[OH:29].[CH3:1][O-:2].Br[CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]2[c:14]2[c:15]3[c:16]([c:17](-[c:18]4[cH:19][cH:20][cH:21][cH:22][c:23]4[Cl:24])[cH:25][c:26]12)[C:27](=[O:28])N[C:30]3=[O:31]>>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]2[c:14]2[... | CO.C[O-].O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCBr | COCCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)OC3=O | null | null | O1CCOCC1 | Acylation | OtherReaction | aa74ae21e92556b7bfc022aa15b13c3d72fc3a4f78b3baac80a97b35a10dc16e | 28d1aeeff3505343953582dd13040e5ccf99afb73b2ea1712b3b26d6f4b25824 | O=C1OC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[#7;a:4]:[c:5]:[c:6]:[c:7]1:[c:8](:[c:9])-[C;H0;D3;+0:10](=[O;D1;H0:11])-N-[C;H0;D3;+0:12]-1=[O;D1;H0:13].C-[OH;D1;+0:14].[C;D1;H3:15]-[O-;H0;D1:16]>>[C;D1;H3:15]-[O;H0;D2;+0:16]-[CH2;D2;+0:1]-[C:2]-[C:3]-[#7;a:4]:[c:5]:[c:6]:[c:7]1:[c:8](:[c:9])-[C;H0;D3;+0:10](=[O;D1;H0:11])-[O;H0;D2;+0:1... | null | [] | null | null | null | null | A solution of the bromide (58) (50 mg, 0.103 mmol) prepared as described in example 172 and sodium methoxide (35.2 mg, 0.65 mmol) in methanol (0.5 mL) and p-dioxane (8 mL) was refluxed for 3 h. The solution was acidified with 2N HCl, extracted with ethyl acetate and the organic layer was dried, the drying agent was rem... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Unsubstituted dicarboximide.Methanol | Anhydride.Ester.Ester.Ether | C1NCc2c1ccc1[nH]c3ccccc3c21 | C1OCc2c1ccc1[nH]c3ccccc3c21 | c1ccccc1.C1OCc2c1ccc1[nH]c3ccccc3c21 | HBr | O1CCOCC1 | null | null | CO.C[O-].O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCCBr>O1CCOCC1>COCCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)OC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b197a92233c64fc5a8d67b98bc499b20 | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4Cl)cc1n2CCC(=O)O)C(=O)NC3=O.N>>COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4Cl)cc1n2CCC(N)=O)C(=O)NC3=O | ClC1=C(C(=CC=C1)Cl)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)O.N>>ClC1=C(C(=CC=C1)Cl)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)N | O[C:26]([CH2:25][CH2:24][n:23]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8][c:7]2[c:9]2[c:10]3[c:11]([c:12](-[c:13]4[c:14]([Cl:15])[cH:16][cH:17][cH:18][c:19]4[Cl:20])[cH:21][c:22]21)[C:29](=[O:30])[NH:31][C:32]3=[O:33])=[O:28].[NH3:27]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[c:9]1[c:10]3[c:11]([c:12](-[c:13... | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4Cl)cc1n2CCC(=O)O)C(=O)NC3=O.N | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4Cl)cc1n2CCC(N)=O)C(=O)NC3=O | null | null | null | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH3;D0;+0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 73 | [{"value": 73.0, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of acid (244) (0.23 g, 0.48 mmol) prepared as described in example 204 according to the procedure described in example 207, except that concentrated ammonia (˜30%, 20 mL) was added as the amine, gave amide (250) (0.17 g, 73%) as a yellow powder, mp 261–264° C. 1H NMR δ [(CD3)2SO] 11.19 (br s, 1H), 8.50 (d, J=2... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | HO- | null | null | null | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4Cl)cc1n2CCC(=O)O)C(=O)NC3=O.N>>COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4Cl)cc1n2CCC(N)=O)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-63b33118c5334130939d6c3e5f27f1ba | COc1ccc2c(c1)c1c3c(c(-c4ccccc4)cc1n2CCC(=O)NCCN(C)C)C(=O)NC3=O>>CN(C)CCNC(=O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O | CN(CCNC(CCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)OC)=O)C.N>>CN(CCNC(CCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O)=O)C | C[O:16][c:15]1[cH:14][cH:13][c:12]2[n:11]([CH2:10][CH2:9][C:7]([NH:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])=[O:8])[c:30]3[c:19]([c:18]2[cH:17]1)[c:20]1[c:21]([c:22](-[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[cH:29]3)[C:31](=[O:32])[NH:33][C:34]1=[O:35]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][C:7](=[O:8])[CH2:9][CH2... | COc1ccc2c(c1)c1c3c(c(-c4ccccc4)cc1n2CCC(=O)NCCN(C)C)C(=O)NC3=O | CN(C)CCNC(=O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O | null | null | O | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | Reaction of methyl ether (247) (70 mg, 0.14 mmol) prepared as described in example 207 according to the procedure described in example 81, except that the reaction mixture was diluted with water, basified by the addition of concentrated ammonia and extracted with ethyl acetate. The organic layer was dried, the drying a... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | Other | O | null | null | COc1ccc2c(c1)c1c3c(c(-c4ccccc4)cc1n2CCC(=O)NCCN(C)C)C(=O)NC3=O>O>CN(C)CCNC(=O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-43b0467513d5487d801b433d3756f736 | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4Cl)cc1n2CCC(N)=O)C(=O)NC3=O>>NC(=O)CCn1c2ccc(O)cc2c2c3c(c(-c4c(Cl)cccc4Cl)cc21)C(=O)NC3=O | ClC1=C(C(=CC=C1)Cl)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)N.O1CCCC1>>ClC1=C(C(=CC=C1)Cl)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)N | C[O:11][c:10]1[cH:9][cH:8][c:7]2[n:6]([CH2:5][CH2:4][C:2]([NH2:1])=[O:3])[c:27]3[c:14]([c:13]2[cH:12]1)[c:15]1[c:16]([c:17](-[c:18]2[c:19]([Cl:20])[cH:21][cH:22][cH:23][c:24]2[Cl:25])[cH:26]3)[C:28](=[O:29])[NH:30][C:31]1=[O:32]>>[NH2:1][C:2](=[O:3])[CH2:4][CH2:5][n:6]1[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]2[c:... | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4Cl)cc1n2CCC(N)=O)C(=O)NC3=O | NC(=O)CCn1c2ccc(O)cc2c2c3c(c(-c4c(Cl)cccc4Cl)cc21)C(=O)NC3=O | null | null | C(C)(=O)OCC | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 59 | [{"value": 59.0, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.0, "product": "ClC1=C(C(=CC=C1)Cl)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of methyl ether (250) (80 mg, 0.17 mmol)) prepared as described in example 210 according to The procedure described in example 80, followed by chromatography on silica eluting with ethyl acetate then tetrahydrofuran and trituration from ethyl acetate, gave amide (258) (47 mg, 59%) as an orange powder, mp 327–3... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | Other | C(C)(=O)OCC | null | null | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4Cl)cc1n2CCC(N)=O)C(=O)NC3=O>C(C)(=O)OCC>NC(=O)CCn1c2ccc(O)cc2c2c3c(c(-c4c(Cl)cccc4Cl)cc21)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-66d5617ee3174b04900152f40608af0f | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4OC)cc1n2CCC(=O)NCCN(C)C)C(=O)NC3=O.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCn1ccnc1>>COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCC(=O)NCCN(C)C | ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)NCCN(C)C.OC1=CC=2C=3C4=C(C(=CC3N(C2C=C1)CCCN1C=NC=C1)C1=CC=CC=C1)C(NC4=O)=O>>ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)NCCN(C)C | COc1ccc2c(c1)[c:13]1[c:12]([cH:11][c:10](-[c:9]3[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]3[Cl:8])[c:15]3[c:14]1[C:19](=[O:20])[NH:18][C:16]3=[O:17])[n:28]2[CH2:29][CH2:30][C:31](=[O:32])[NH:33][CH2:34][CH2:35][N:36]([CH3:37])[CH3:38].O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2[c:21]2[cH:22][c:23]([OH:24])[cH:25][cH:26][c:27]2n1CC... | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4OC)cc1n2CCC(=O)NCCN(C)C)C(=O)NC3=O.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCn1ccnc1 | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCC(=O)NCCN(C)C | null | null | null | Miscellaneous | OtherReaction | 04e2bfa40d4eefbd80f022dff1597ce73473c2e77c3cc98a6101158bfaeb33ee | 0404f73f8bae062b3c383035c98e95881c2a09658febdbde66fa05b90ea55863 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-O-c1:c:c:c2:[n;H0;D3;+0:1](-[C:2]-[C:3]-[C:4](-[#7:5])=[O;D1;H0:6]):[c:7](:[c:8]):[c;H0;D3;+0:9](:[c:10]3:[c:11]-[C:12](=[O;D1;H0:13])-[#7:14]-[C:15]-3=[O;D1;H0:16]):c:2:c:1.O=C1-N-C(=O)-c2:c-1:c(-c1:c:c:c:c:c:1):c:c1:c:2:[c;H0;D3;+0:17]2:[c:18]:[c:19]:[c:20]:[c:21]:[c;H0;D3;+0:22]:2:n:1-C-C-C-n1:c:c:n:c:1>>[#7:5]-[C... | 83 | [{"value": 83.0, "product": "ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)NCCN(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Reaction of methyl ether (252) prepared as described in example 212 (80 mg, 0.15 mmol) according to The procedure described in example 80, except that the reaction was performed at 0° C. for 2 hours and chromatography was performed eluting with ethyl acetate/methanol/triethylamine (1:0:0 to 3:1:trace), gave amide (260)... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Unsubstituted dicarboximide | null | C1NCc2c1ccc1nc3ccccc3c21.c1ccccc1.c1c[nH]cn1.c1ccc2nc3ccc4c(c3c2c1)CNC4 | C1NCc2c1ccc1nc3ccccc3c21 | c1ccccc1.C1NCc2c1ccc1nc3ccccc3c21 | HO- | null | null | 2 | COc1ccc2c(c1)c1c3c(c(-c4c(Cl)cccc4OC)cc1n2CCC(=O)NCCN(C)C)C(=O)NC3=O.O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CCCn1ccnc1>>COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCC(=O)NCCN(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2d72889ef0374e16a7cf146871cfef15 | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCC(=O)NCCN(C)C>>COc1ccccc1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCC(=O)NCCN(C)C | ClC1=C(C(=CC=C1)OC)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)NCCN(C)C>>CN(CCNC(CCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)OC)C(NC3=O)=O)O)=O)C | Cl[c:7]1[cH:6][cH:5][cH:4][c:3]([O:2][CH3:1])[c:8]1-[c:9]1[cH:10][c:11]2[c:12]([c:13]3[c:14]1[C:15](=[O:16])[NH:17][C:18]3=[O:19])[c:20]1[cH:21][c:22]([OH:23])[cH:24][cH:25][c:26]1[n:27]2[CH2:28][CH2:29][C:30](=[O:31])[NH:32][CH2:33][CH2:34][N:35]([CH3:36])[CH3:37]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1-[c:9... | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCC(=O)NCCN(C)C | COc1ccccc1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCC(=O)NCCN(C)C | null | [Pd].[Pd] | C(C)(=O)OCC.CO | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[c:5]):[c:6]>>[c:6]:[c:4](-[c:5]):[cH;D2;+0:1]:[c:2]:[c:3] | 17.1 | [{"value": 16.0, "product": "CN(CCNC(CCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)OC)C(NC3=O)=O)O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.1, "product": "CN(CCNC(CCN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)OC)C(NC3=O)=O)O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of amide (260) (40 mg, 0.07 mmol)) prepared as described in example 219 in ethyl acetate/methanol (1:1, 80 mL) was added 5% Pd-C (catalytic). The resulting suspension was hydrogenated at 60 psi with stirring for 4 days, with additional portions of Pd-C being added every 24 hours. The reaction mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.C1NCc2c1ccc1nc3ccccc3c21 | Other | [Pd].[Pd].C(C)(=O)OCC.CO | null | null | COc1cccc(Cl)c1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCC(=O)NCCN(C)C>[Pd].[Pd].C(C)(=O)OCC.CO>COc1ccccc1-c1cc2c(c3c1C(=O)NC3=O)c1cc(O)ccc1n2CCC(=O)NCCN(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-786dafbcfc7b4dec85251560283dc0a9 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NS(=O)(=O)CCN(C)C)C(=O)NC3=O>>CN(C)CCS(=O)(=O)NC(=O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)NS(=O)(=O)CCN(C)C>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)NS(=O)(=O)CCN(C)C | C[O:19][c:18]1[cH:17][cH:16][c:15]2[n:14]([CH2:13][CH2:12][C:10]([NH:9][S:6]([CH2:5][CH2:4][N:2]([CH3:1])[CH3:3])(=[O:7])=[O:8])=[O:11])[c:34]3[c:22]([c:21]2[cH:20]1)[c:23]1[c:24]([c:25](-[c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]2[Cl:32])[cH:33]3)[C:35](=[O:36])[NH:37][C:38]1=[O:39]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5]... | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NS(=O)(=O)CCN(C)C)C(=O)NC3=O | CN(C)CCS(=O)(=O)NC(=O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | null | null | C([O-])(O)=O.[Na+] | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 23.4 | [{"value": 23.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)NS(=O)(=O)CCN(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.4, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)NS(=O)(=O)CCN(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired... | null | null | null | null | Reaction of methyl ether (267) (35 mg, 0.06 mmol) prepared as described in example 224 according to the proceedure described in example 81, except that the reaction mixture was diluted with saturated sodium bicarbonate and extracted with ethyl acetate. The organic phase was dried, the drying agent was removed and the s... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | Other | C([O-])(O)=O.[Na+] | null | null | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NS(=O)(=O)CCN(C)C)C(=O)NC3=O>C([O-])(O)=O.[Na+]>CN(C)CCS(=O)(=O)NC(=O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6204db7a9e304c63b085f7c35e35f930 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)O)C(=O)NC3=O>>O=C(O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)O.Cl.[NH+]1=CC=CC=C1>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)O | C[O:11][c:10]1[cH:9][cH:8][c:7]2[n:6]([CH2:5][CH2:4][C:2](=[O:1])[OH:3])[c:26]3[c:14]([c:13]2[cH:12]1)[c:15]1[c:16]([c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[Cl:24])[cH:25]3)[C:27](=[O:28])[NH:29][C:30]1=[O:31]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][n:6]1[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]2[c:14]2[c:15]... | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)O)C(=O)NC3=O | O=C(O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 50 | [{"value": 50.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Demethylation of (116) prepared as described in example 229 with pyridinium hydrochloride using the procedure described in example 81 gave (117) (50%) as a yellow powder, mp 286° C. 1H NMR δ [(CD3)2SO] 12.40 (br, 1H), 11.06 (br s, 1H), 9.37 (br s, 1H), 8.37 (d, J=2.4 Hz, 1H), 7.81 (s, 1H), 7.59 (d, J=8.7 Hz, 1H), 7.57 ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | Other | null | null | null | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)O)C(=O)NC3=O>>O=C(O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0f624640443e434cbe5f5c9f361c5e94 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(N)=O)C(=O)NC3=O>>NC(=O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)N.B(Br)(Br)Br>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)N | C[O:11][c:10]1[cH:9][cH:8][c:7]2[n:6]([CH2:5][CH2:4][C:2]([NH2:1])=[O:3])[c:26]3[c:14]([c:13]2[cH:12]1)[c:15]1[c:16]([c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[Cl:24])[cH:25]3)[C:27](=[O:28])[NH:29][C:30]1=[O:31]>>[NH2:1][C:2](=[O:3])[CH2:4][CH2:5][n:6]1[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]2[c:14]2[c:1... | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(N)=O)C(=O)NC3=O | NC(=O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 77 | [{"value": 77.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Demethylation of (118) prepared as described in example 231 with BBr3 using the procedure described in example 80 gave (119) as a yellow/orange powder (77%), mp 319–322° C. 1H NMR δ [(CD3)2SO] 11.06 (br s, 1H), 9.36 (br s, 1H), 8.37 (d, J=2.4 Hz, 1H), 7.77 (s, 1H), 7.60–7.55 (m, 2H), 7.52–7.43 (m, 3H), 7.35 (br, 1H), 7... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | Other | null | null | null | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(N)=O)C(=O)NC3=O>>NC(=O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ebf2c83b161a4451bd0502da9dbb9704 | NCCN1CCOCC1.O=C(O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O>>COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NCCN1CCOCC1)C(=O)NC3=O | ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)O.C(C(=O)Cl)(=O)Cl.NCCN1CCOCC1>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)NCCN2CCOCC2 | [NH2:27][CH2:28][CH2:29][N:30]1[CH2:31][CH2:32][O:33][CH2:34][CH2:35]1.O[C:25]([CH2:24][CH2:23][n:22]1[c:6]2[cH:5][cH:4][c:3]([OH:2])[cH:8][c:7]2[c:9]2[c:10]3[c:11]([c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[Cl:19])[cH:20][c:21]21)[C:36](=[O:37])[NH:38][C:39]3=[O:40])=[O:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]... | NCCN1CCOCC1.O=C(O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NCCN1CCOCC1)C(=O)NC3=O | null | null | null | Acylation | OtherReaction | e490eebb477043dc0542732dd7a6ce49276641802836b4489c620def21f9d46c | fcf68d457905b35c628fee285772653b3fd6812b4e55ecf3f563dfc9713d647a | O=C(CCn1c2ccccc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O)NCCN1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C;D1;H3:12]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C:10]-[C:9] | 73 | [{"value": 73.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)NCCN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of acid (117) prepared as described in example 230 with oxalyl chloride followed by N-(2-aminoethyl)morpholine using the procedure described in example 207 gave the amide (120) (73%) as a yellow powder, mp 174–176° C. 1H NMR δ [(CD3)2SO] 11.12 (br s, 1H), 8.51 (d, J=2.6 Hz, 1H), 7.77 (s, 1H), 7.74 (t, J=5.6 Hz... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | Ether.Secondary amide | null | null | c1ccccc1.C1COCC[NH]1.C1NCc2c1ccc1[nH]c3ccccc3c21 | null | null | null | null | NCCN1CCOCC1.O=C(O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O>>COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NCCN1CCOCC1)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7b6a5fef751a4360973346568a5ff73a | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NCCN1CCOCC1)C(=O)NC3=O>>O=C(CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O)NCCN1CCOCC1 | ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)NCCN2CCOCC2.B(Br)(Br)Br>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)NCCN2CCOCC2 | C[O:10][c:9]1[cH:8][cH:7][c:6]2[n:5]([CH2:4][CH2:3][C:2](=[O:1])[NH:31][CH2:32][CH2:33][N:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)[c:25]3[c:13]([c:12]2[cH:11]1)[c:14]1[c:15]([c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[Cl:23])[cH:24]3)[C:26](=[O:27])[NH:28][C:29]1=[O:30]>>[O:1]=[C:2]([CH2:3][CH2:4][n:5]1[c:6]... | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NCCN1CCOCC1)C(=O)NC3=O | O=C(CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O)NCCN1CCOCC1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(CCn1c2ccccc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O)NCCN1CCOCC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 64 | [{"value": 64.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)NCCN2CCOCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Demethylation of (120) prepared as described in example 233 with BBr3 using the procedure described in example 80 except that the reaction time was 16 h gave (121) as a yellow powder (64%), mp 143–148° C. (dec). 1H NMR δ [(CD3)2SO] 11.05 (s, 1H), 9.35 (s, 1H), 8.36 (d, J=2.4 Hz, 1H), 7.74 (t, J=5.6 Hz, 1H), 7.71 (s, 1H... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.C1COCC[NH]1.C1NCc2c1ccc1[nH]c3ccccc3c21 | Other | null | null | 16 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NCCN1CCOCC1)C(=O)NC3=O>>O=C(CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O)NCCN1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-87762ef3bc394568a794bebe60f282eb | CC1(C)CC(N)CC(C)(C)N1.O=C(O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O>>COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NC1CC(C)(C)NC(C)(C)C1)C(=O)NC3=O | ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)O.C(C(=O)Cl)(=O)Cl.NC1CC(NC(C1)(C)C)(C)C>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)NC2CC(NC(C2)(C)C)(C)C | [NH2:27][CH:28]1[CH2:29][C:30]([CH3:31])([CH3:32])[NH:33][C:34]([CH3:35])([CH3:36])[CH2:37]1.O[C:25]([CH2:24][CH2:23][n:22]1[c:6]2[cH:5][cH:4][c:3]([OH:2])[cH:8][c:7]2[c:9]2[c:10]3[c:11]([c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[Cl:19])[cH:20][c:21]21)[C:38](=[O:39])[NH:40][C:41]3=[O:42])=[O:26]>>[CH3:1][O:2][... | CC1(C)CC(N)CC(C)(C)N1.O=C(O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NC1CC(C)(C)NC(C)(C)C1)C(=O)NC3=O | null | null | null | Acylation | OtherReaction | e490eebb477043dc0542732dd7a6ce49276641802836b4489c620def21f9d46c | fcf68d457905b35c628fee285772653b3fd6812b4e55ecf3f563dfc9713d647a | O=C(CCn1c2ccccc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O)NC1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12]>>[C;D1;H3:13]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C:10](-[C:9])-[C:12] | 72 | [{"value": 72.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)NC2CC(NC(C2)(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of acid (117) prepared as described in example 230 with oxalyl chloride followed by 4-amino-(2,2,6,6-tetramethyl)piperidine using the procedure described in example 207 gave the amide (124) (72%) as a yellow powder, mp 155–160° C. (dec). 1H NMR δ [(CD3)2SO] 11.12 (br, 1H), 8.51 (d, J=2.6 Hz, 1H), 7.78 (s, 1H),... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | Ether.Secondary amide | null | null | c1ccccc1.C1CCNCC1.C1NCc2c1ccc1[nH]c3ccccc3c21 | null | null | null | null | CC1(C)CC(N)CC(C)(C)N1.O=C(O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O>>COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NC1CC(C)(C)NC(C)(C)C1)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-23f0286140094cc399e0b44e036c79d9 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NC1CC(C)(C)NC(C)(C)C1)C(=O)NC3=O>>CC1(C)CC(NC(=O)CCn2c3ccc(O)cc3c3c4c(c(-c5ccccc5Cl)cc32)C(=O)NC4=O)CC(C)(C)N1 | ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)NC2CC(NC(C2)(C)C)(C)C.B(Br)(Br)Br>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)NC2CC(NC(C2)(C)C)(C)C | C[O:16][c:15]1[cH:14][cH:13][c:12]2[n:11]([CH2:10][CH2:9][C:7]([NH:6][CH:5]3[CH2:4][C:2]([CH3:1])([CH3:3])[NH:41][C:38]([CH3:39])([CH3:40])[CH2:37]3)=[O:8])[c:31]3[c:19]([c:18]2[cH:17]1)[c:20]1[c:21]([c:22](-[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[Cl:29])[cH:30]3)[C:32](=[O:33])[NH:34][C:35]1=[O:36]>>[CH3:1][C:2]1([... | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NC1CC(C)(C)NC(C)(C)C1)C(=O)NC3=O | CC1(C)CC(NC(=O)CCn2c3ccc(O)cc3c3c4c(c(-c5ccccc5Cl)cc32)C(=O)NC4=O)CC(C)(C)N1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(CCn1c2ccccc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O)NC1CCNCC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 47 | [{"value": 47.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)NC2CC(NC(C2)(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | Demethylation of (124) prepared as described in example 237 with BBr3 using the procedure described in example 80 except that the reaction time was 48 h gave (125) as a yellow powder (47%), mp 293–299° C. (dec). 1H NMR δ [(CD3)2SO] 11.08 (br s, 1H), 9.38 (br s, 1H), 8.72 (br, 1H), 8.37 (d, J=2.4 Hz, 1H), 7.83 (d, J=7.1... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1CCNCC1.c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | Other | null | null | 48 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NC1CC(C)(C)NC(C)(C)C1)C(=O)NC3=O>>CC1(C)CC(NC(=O)CCn2c3ccc(O)cc3c3c4c(c(-c5ccccc5Cl)cc32)C(=O)NC4=O)CC(C)(C)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bf82ca84eb494da698eff1c7d6330ab7 | C[C@@H]1CNC[C@H](C)N1.O=C(O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O>>COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)N1C[C@@H](C)N[C@@H](C)C1)C(=O)NC3=O | ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)O.C(C(=O)Cl)(=O)Cl.C[C@@H]1N[C@@H](CNC1)C>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)N2C[C@H](N[C@H](C2)C)C | [NH:27]1[CH2:28][C@@H:29]([CH3:30])[NH:31][C@@H:32]([CH3:33])[CH2:34]1.O[C:25]([CH2:24][CH2:23][n:22]1[c:6]2[cH:5][cH:4][c:3]([OH:2])[cH:8][c:7]2[c:9]2[c:10]3[c:11]([c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[Cl:19])[cH:20][c:21]21)[C:35](=[O:36])[NH:37][C:38]3=[O:39])=[O:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]... | C[C@@H]1CNC[C@H](C)N1.O=C(O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)N1C[C@@H](C)N[C@@H](C)C1)C(=O)NC3=O | null | null | null | Acylation | OtherReaction | d5514a6760e82f876a7c9f84c493e9b26fbd78acff107645e987694b09882cec | 71f673d14b505054b867264e6efffeeae2c2502635894b4948f22bc3c49a295b | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2ccccc2n1CCC(=O)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8].[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[C;D1;H3:15]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-1 | 76 | [{"value": 76.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)N2C[C@H](N[C@H](C2)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of acid (117) prepared as described in example 230 with oxalyl chloride followed by cis-2,6-dimethylpiperazine using the procedure described in example 207 gave the amide (126) (76%) as a yellow powder, mp 168–173° C. (dec). 1H NMR δ [(CD3)2SO] 11.13 (br, 1H), 8.52 (d, J=2.6 Hz, 1H), 7.80 (s, 0.5H), 7.76 (s, 0... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Secondary amine | Ether.Tertiary amide | C1CNCCN1 | C1C[NH]CCN1 | c1ccccc1.C1C[NH]CCN1.C1NCc2c1ccc1[nH]c3ccccc3c21 | null | null | null | null | C[C@@H]1CNC[C@H](C)N1.O=C(O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O>>COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)N1C[C@@H](C)N[C@@H](C)C1)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fc10689e4ed84f96812f897b3db7adea | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)N1C[C@@H](C)N[C@@H](C)C1)C(=O)NC3=O>>C[C@@H]1CN(C(=O)CCn2c3ccc(O)cc3c3c4c(c(-c5ccccc5Cl)cc32)C(=O)NC4=O)C[C@H](C)N1 | ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)N2C[C@H](N[C@H](C2)C)C.B(Br)(Br)Br>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)N2C[C@H](N[C@H](C2)C)C | C[O:14][c:13]1[cH:12][cH:11][c:10]2[n:9]([CH2:8][CH2:7][C:5]([N:4]3[CH2:3][C@@H:2]([CH3:1])[NH:38][C@@H:36]([CH3:37])[CH2:35]3)=[O:6])[c:29]3[c:17]([c:16]2[cH:15]1)[c:18]1[c:19]([c:20](-[c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[Cl:27])[cH:28]3)[C:30](=[O:31])[NH:32][C:33]1=[O:34]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[... | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)N1C[C@@H](C)N[C@@H](C)C1)C(=O)NC3=O | C[C@@H]1CN(C(=O)CCn2c3ccc(O)cc3c3c4c(c(-c5ccccc5Cl)cc32)C(=O)NC4=O)C[C@H](C)N1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2ccccc2n1CCC(=O)N1CCNCC1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 38 | [{"value": 38.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)N2C[C@H](N[C@H](C2)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | Demethylation of (126) prepared as described in example 239 (with BBr3 using the procedure described in example 80 except that the reaction time was 48 h gave (127) as a yellow powder (38%), mp 220–224° C. (dec). 1H NMR δ [(CD3)2SO] 11.07 (br s, 1H) 9.36 (br s, 1H), 8.72 (br, 1H), 8.34 br, 1H), 7.72 (s, 0.5H), 7.71 (s,... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1CNCC[NH]1.c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21 | Other | null | null | 48 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)N1C[C@@H](C)N[C@@H](C)C1)C(=O)NC3=O>>C[C@@H]1CN(C(=O)CCn2c3ccc(O)cc3c3c4c(c(-c5ccccc5Cl)cc32)C(=O)NC4=O)C[C@H](C)N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-433c46922dbe4aab9fda6d1573802cf3 | NCCc1c[nH]cn1.O=C(O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O>>COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NCCc1cnc[nH]1)C(=O)NC3=O | ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)O.C(C(=O)Cl)(=O)Cl.NCCC1=CNC=N1>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)NCCC2=CN=CN2 | [NH2:27][CH2:28][CH2:29][c:30]1[cH:31][nH:32][cH:33][n:34]1.O[C:25]([CH2:24][CH2:23][n:22]1[c:6]2[cH:5][cH:4][c:3]([OH:2])[cH:8][c:7]2[c:9]2[c:10]3[c:11]([c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[Cl:19])[cH:20][c:21]21)[C:35](=[O:36])[NH:37][C:38]3=[O:39])=[O:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:... | NCCc1c[nH]cn1.O=C(O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NCCc1cnc[nH]1)C(=O)NC3=O | null | null | null | Acylation | OtherReaction | e490eebb477043dc0542732dd7a6ce49276641802836b4489c620def21f9d46c | fcf68d457905b35c628fee285772653b3fd6812b4e55ecf3f563dfc9713d647a | O=C(CCn1c2ccccc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O)NCCc1cnc[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[OH;D1;+0:5]-[c:6](:[c:7]):[c:8].[NH2;D1;+0:9]-[C:10]-[C:11]-[c:12]1:[c:13]:[nH;D2;+0:14]:[c:15]:[n;H0;D2;+0:16]:1>>[C;D1;H3:17]-[O;H0;D2;+0:5]-[c:6](:[c:7]):[c:8].[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:9]-[C:10]-[C:11]-[c:12]1:[c:13]:[n;H0;D2;+0:14]:[c:15]:[nH;D2;... | 81 | [{"value": 81.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)NCCC2=CN=CN2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of acid (117) prepared as described in example 230 with oxalyl chloride followed by histamine using the procedure described in example 207 gave the amide (128) (81%) as a yellow powder, mp 144–149° C. (dec). 1H NMR δ [(CD3)2SO] 11.12 (br, 1H), 8.52 (d, J=2.6 Hz, 1H), 7.91 (t, J=5.5 Hz, 1H), 7.76 (s, 1H), 7.69 ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Primary amine | Ether.Secondary amide | null | null | c1ccccc1.c1c[nH]cn1.C1NCc2c1ccc1[nH]c3ccccc3c21 | null | null | null | null | NCCc1c[nH]cn1.O=C(O)CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O>>COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NCCc1cnc[nH]1)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b59472ebce341ce8560e7ca3d38bb3e | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NCCc1cnc[nH]1)C(=O)NC3=O>>O=C(CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O)NCCc1cnc[nH]1 | ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)OC)CCC(=O)NCCC2=CN=CN2.B(Br)(Br)Br>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)NCCC2=CN=CN2 | C[O:10][c:9]1[cH:8][cH:7][c:6]2[n:5]([CH2:4][CH2:3][C:2](=[O:1])[NH:31][CH2:32][CH2:33][c:34]3[cH:35][n:36][cH:37][nH:38]3)[c:25]3[c:13]([c:12]2[cH:11]1)[c:14]1[c:15]([c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[Cl:23])[cH:24]3)[C:26](=[O:27])[NH:28][C:29]1=[O:30]>>[O:1]=[C:2]([CH2:3][CH2:4][n:5]1[c:6]2[cH:7][cH:... | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NCCc1cnc[nH]1)C(=O)NC3=O | O=C(CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O)NCCc1cnc[nH]1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(CCn1c2ccccc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O)NCCc1cnc[nH]1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 46 | [{"value": 46.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC(=O)NCCC2=CN=CN2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | Demethylation of (128) prepared as described in example 241 with BBr3 using the procedure described in example 80 except that the reaction time was 48 h gave (129) as a yellow powder (46%), mp 158–162° C. (dec). 1H NMR δ [(CD3)2SO] 11.75 (br, 1H), 11.05 (br s, 1H), 9.36 (br s, 1H), 8.37 (d, J=2.4 Hz, 1H), 7.91 (t, J=5.... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1c[nH]cn1.C1NCc2c1ccc1[nH]c3ccccc3c21 | Other | null | null | 48 | COc1ccc2c(c1)c1c3c(c(-c4ccccc4Cl)cc1n2CCC(=O)NCCc1cnc[nH]1)C(=O)NC3=O>>O=C(CCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O)NCCc1cnc[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d9e8ac3d46b14af1810494a565aed42a | COC(=O)CN=[N+]=[N-].COc1cc(C=O)ccc1OCc1ccccc1>>COC(=O)C(=Cc1ccc(OCc2ccccc2)c(OC)c1)N=[N+]=[N-] | C(C1=CC=CC=C1)OC1=C(C=C(C=O)C=C1)OC.N(=[N+]=[N-])CC(=O)OC.[Na].C[O-].[Na+]>>COC(C(=CC1=CC(=C(C=C1)OCC1=CC=CC=C1)OC)N=[N+]=[N-])=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][N:23]=[N+:24]=[N-:25].O=[CH:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]([O:20][CH3:21])[cH:22]1>>[CH3:1][O:2][C:3](=[O:4])[C:5](=[CH:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]([O:20][CH3:21]... | COC(=O)CN=[N+]=[N-].COc1cc(C=O)ccc1OCc1ccccc1 | COC(=O)C(=Cc1ccc(OCc2ccccc2)c(OC)c1)N=[N+]=[N-] | null | null | CO | C-C Coupling | Aldol condensation | a86984aeb4a9963534e0b081b0ecca18455fda1775f36ce168d1ca4cf966df3e | 203dd34a20dceaf1737adbf20e01b43c2424e4e4b1722d942d1a796d895396e6 | c1ccc(COc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[#7:10]=[#7;+:11]=[N;-;D1;H0:12]>>[C;D1;H3:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:9](-[#7:10]=[#7;+:11]=[N;-;D1;H0:12])=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 73 | [{"value": 73.0, "product": "COC(C(=CC1=CC(=C(C=C1)OCC1=CC=CC=C1)OC)N=[N+]=[N-])=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.5, "product": "COC(C(=CC1=CC(=C(C=C1)OCC1=CC=CC=C1)OC)N=[N+]=[N-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 45 | MINUTE | A solution of the 4-Benzyloxy-3-methoxy-benzaldehyde (12.0 g, 49.6 mmol) and methyl azidoacetate (23 g, 0.200 mol) in methanol (50 mL) was added over 30 min to a cooled (ice-salt bath) solution of sodium methoxide which had been prepared from addition of methanol (80 mL) to sodium (3.4 g, 0.149 mol). The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester | null | null | c1ccccc1.c1ccccc1 | HO- | CO | 0 | 0.75 | COC(=O)CN=[N+]=[N-].COc1cc(C=O)ccc1OCc1ccccc1>CO>COC(=O)C(=Cc1ccc(OCc2ccccc2)c(OC)c1)N=[N+]=[N-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5b03fb00651042f0af60dea939965173 | COC(=O)C(=Cc1ccc(OCc2ccccc2)c(OC)c1)N=[N+]=[N-]>>COC(=O)c1cc2cc(OC)c(OCc3ccccc3)cc2[nH]1 | COC(C(=CC1=CC(=C(C=C1)OCC1=CC=CC=C1)OC)N=[N+]=[N-])=O>>COC(=O)C=1NC2=CC(=C(C=C2C1)OC)OCC1=CC=CC=C1 | [N-]=[N+]=[N:23][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][c:7]1[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([O:10][CH3:11])[c:12]([O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][c:22]2[... | COC(=O)C(=Cc1ccc(OCc2ccccc2)c(OC)c1)N=[N+]=[N-] | COC(=O)c1cc2cc(OC)c(OCc3ccccc3)cc2[nH]1 | null | null | C=1(C(=CC=CC1)C)C | Aromatic Heterocycle Formation | OtherReaction | edb9971602bfa0422050f727deecbcfa88df9e7fbb5c6b709e0e7c05fb641641 | 92e44103d9eed82e18506de89438be8bcf71f9d4943ea64c754ba56033058a29 | c1ccc(COc2ccc3cc[nH]c3c2)cc1 | [C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](=[CH;D2;+0:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11])-[N;H0;D2;+0:12]=[N+]=[N-]>>[C;D1;H3:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7](:[c:8]):[c;H0;D3;+0:9](:[c:10]:[c:11]):[nH;D2;+0:12]:1 | null | [] | null | null | null | null | A solution of the azidocinnamate (55) (12.2 g, 36.0 mmol) prepared as described in example 247 in xylene (300 mL) was added dropwise to refluxing xylene (100 mL) over 1.5 h, the reaction mixture was heated at reflux for a further 15 min and then most of the xylene was removed by distillation. The residue, on cooling to... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Azide | Ester | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccc2[nH]ccc2c1.c1ccccc1 | Other | C=1(C(=CC=CC1)C)C | null | null | COC(=O)C(=Cc1ccc(OCc2ccccc2)c(OC)c1)N=[N+]=[N-]>C=1(C(=CC=CC1)C)C>COC(=O)c1cc2cc(OC)c(OCc3ccccc3)cc2[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2762c7091e4841c693b05eddf337a72e | COC(=O)c1cc2cc(OC)c(OCc3ccccc3)cc2[nH]1>>COc1cc2cc(C=O)[nH]c2cc1OCc1ccccc1 | [OH-].[Na+].COC(=O)C=1NC2=CC(=C(C=C2C1)OC)OCC1=CC=CC=C1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>>C(C1=CC=CC=C1)OC1=C(C=C2C=C(NC2=C1)C=O)OC | CO[C:8]([c:7]1[cH:6][c:5]2[cH:4][c:3]([O:2][CH3:1])[c:13]([O:14][CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:12][c:11]2[nH:10]1)=[O:9]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([CH:8]=[O:9])[nH:10][c:11]2[cH:12][c:13]1[O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | COC(=O)c1cc2cc(OC)c(OCc3ccccc3)cc2[nH]1 | COc1cc2cc(C=O)[nH]c2cc1OCc1ccccc1 | null | [O-2].[O-2].[Mn+4] | O1CCCC1 | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | c1ccc(COc2ccc3cc[nH]c3c2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 82 | [{"value": 82.0, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C=C(NC2=C1)C=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.7, "product": "C(C1=CC=CC=C1)OC1=C(C=C2C=C(NC2=C1)C=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | To a solution of the ester (56) (1.0 g, 3.22 mmol) prepared as described in example 248 in tetrabydrofuran (10 mL) was added a suspension of lithium aluminum hydride (0.150 g, 3.86 mmol) in tetrahydrofuran (10 mL) dropwise, the reaction mixture was stirred at room temperature for 20 min. Water (1 mL) was added dropwise... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | [O-2].[O-2].[Mn+4].O1CCCC1 | null | 0.333333 | COC(=O)c1cc2cc(OC)c(OCc3ccccc3)cc2[nH]1>[O-2].[O-2].[Mn+4].O1CCCC1>COc1cc2cc(C=O)[nH]c2cc1OCc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c4c6b20ef05246859197c01fa797a32d | COc1cc2cc(C=Cc3ccccc3Cl)[nH]c2cc1OCc1ccccc1.O=C1C=CC(=O)N1>>COc1cc2c3c([nH]c2cc1OCc1ccccc1)CC(c1ccccc1Cl)C1C(=O)NC(=O)C31 | C(C1=CC=CC=C1)OC1=C(C=C2C=C(NC2=C1)C=CC1=C(C=CC=C1)Cl)OC.C1(C=CC(N1)=O)=O>>C(C1=CC=CC=C1)OC=1C(=CC=2C=3C4C(C(CC3NC2C1)C1=C(C=CC=C1)Cl)C(NC4=O)=O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]2[cH:6][c:7]([CH:20]=[CH:21][c:22]3[cH:23][cH:24][cH:25][cH:26][c:27]3[Cl:28])[nH:8][c:9]2[cH:10][c:11]1[O:12][CH2:13][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[CH:29]1=[CH:35][C:33](=[O:34])[NH:32][C:30]1=[O:31]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]3[c:7]([nH:8][c:9]2[cH:10][c:11]1[O:12][... | COc1cc2cc(C=Cc3ccccc3Cl)[nH]c2cc1OCc1ccccc1.O=C1C=CC(=O)N1 | COc1cc2c3c([nH]c2cc1OCc1ccccc1)CC(c1ccccc1Cl)C1C(=O)NC(=O)C31 | null | null | null | C-C Coupling | OtherReaction | f4dfd9249675065a438272ee31ebbe56b42434dbbe67b7314944f01b1550fb32 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C1NC(=O)C2C(c3ccccc3)Cc3[nH]c4cc(OCc5ccccc5)ccc4c3C12 | [O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[CH;D2;+0:6]=[CH;D2;+0:7]-1.[c:8]:[c:9]1:[#7;a:10]:[c:11](-[CH;D2;+0:12]=[CH;D2;+0:13]-[c:14](:[c:15]):[c:16]):[cH;D2;+0:17]:[c:18]:1:[c:19]>>[O;D1;H0:1]=[C:2]1-[#7:3]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6]2-[CH;D3;+0:7]-1-[CH;D3;+0:13](-[c:14](:[c:15]):[c:16])-[CH2;D2;+0:12]-[c:... | 87 | [{"value": 87.0, "product": "C(C1=CC=CC=C1)OC=1C(=CC=2C=3C4C(C(CC3NC2C1)C1=C(C=CC=C1)Cl)C(NC4=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of the diene (155) prepared as described in example 255 with maleimide using the procedure described in example 69 gave the adduct (161) as a tan powder (87%), which was used without further purification.
Conditions: See reaction.notes.procedure_details.
Workup: prepared | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]ccc2c1.C1=CCNC1 | c1ccc2c3c([nH]c2c1)CCC1CNCC31 | c1ccccc1.c1ccccc1.c1ccc2c3c([nH]c2c1)CCC1CNCC31 | null | null | null | null | COc1cc2cc(C=Cc3ccccc3Cl)[nH]c2cc1OCc1ccccc1.O=C1C=CC(=O)N1>>COc1cc2c3c([nH]c2cc1OCc1ccccc1)CC(c1ccccc1Cl)C1C(=O)NC(=O)C31 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d22ddd8026f748649d3dd6a766adff05 | COc1cc2c3c([nH]c2cc1OCc1ccccc1)CC(c1ccccc1Cl)C1C(=O)NC(=O)C31>>COc1cc2c(cc1OCc1ccccc1)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | C(C1=CC=CC=C1)OC=1C(=CC=2C=3C4C(C(CC3NC2C1)C1=C(C=CC=C1)Cl)C(NC4=O)=O)OC>>C(C1=CC=CC=C1)OC=1C(=CC=2C=3C4=C(C(=CC3NC2C1)C1=C(C=CC=C1)Cl)C(NC4=O)=O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[nH:17][c:18]1[c:30]2[CH:29]2[CH:28]([CH:20]([c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]3[Cl:27])[CH2:19]1)[C:34](=[O:35])[NH:33][C:31]2=[O:32]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[O:9][CH2:10][c:11]1[cH:... | COc1cc2c3c([nH]c2cc1OCc1ccccc1)CC(c1ccccc1Cl)C1C(=O)NC(=O)C31 | COc1cc2c(cc1OCc1ccccc1)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | null | [O-2].[O-2].[Mn+4] | null | Oxidation | OtherReaction | 3d157ee1e52021ba4f102c0e4bf23d31153db03cc8f65d6ae2d3bbc53db1b830 | 82a3692de44364afcfd8cc4460435180e0752c31812bf6008d75e02664a32947 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3cc(OCc4ccccc4)ccc3c21 | [Cl;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[c:7]2:[#7;a:8]:[c:9]:[c:10]:[c:11]:2-[CH;D3;+0:12]2-[C:13](=[O;D1;H0:14])-[#7:15]-[C:16](=[O;D1;H0:17])-[CH;D3;+0:18]-1-2):[c:19]:[c:20]>>[Cl;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[c:7]2:[#7;a:8]:[c:9]:[c:10]:[c:11]:2:... | 93 | [{"value": 93.0, "product": "C(C1=CC=CC=C1)OC=1C(=CC=2C=3C4=C(C(=CC3NC2C1)C1=C(C=CC=C1)Cl)C(NC4=O)=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Aromatisation of (161) prepared as described in example 261 with manganese dioxide using the procedure described in example 79 gave the carbazole (162) (93%) as an orange powder, mp 260–264° C. 1H NMR δ [(CD3)2SO] 11.86 (s, 1H), 11.01 (s, 1H), 8.43 (s, 1H), 7.58–7.34 (m, 10H), 7.26 (s, 1H), 5.26 (s, 2H), 3.91 (s, 3H). ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2c3c([nH]c2c1)CCC1CNCC31 | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | null | [O-2].[O-2].[Mn+4] | null | null | COc1cc2c3c([nH]c2cc1OCc1ccccc1)CC(c1ccccc1Cl)C1C(=O)NC(=O)C31>[O-2].[O-2].[Mn+4]>COc1cc2c(cc1OCc1ccccc1)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-44e17ed999e24f12a40be8ec409048b0 | COc1ccc2cc(C=O)[nH]c2c1.c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>>COc1ccc2cc(C=Cc3ccccc3)[nH]c2c1 | COC1=CC=C2C=C(NC2=C1)C=O.[Br-].C(C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>COC1=CC=C2C=C(NC2=C1)C=CC1=CC=CC=C1 | O=[CH:9][c:8]1[cH:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:19][c:18]2[nH:17]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][c:8]([CH:9]=[CH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[nH:17][c:18]2[cH:19]1 | COc1ccc2cc(C=O)[nH]c2c1.c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | COc1ccc2cc(C=Cc3ccccc3)[nH]c2c1 | null | null | null | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=Cc1cc2ccccc2[nH]1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[c:6]:[c:7](-[CH2;D2;+0:8]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:9]>>[c:6]:[c:7](-[CH;D2;+0:8]=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5]):[c:9] | 94 | [{"value": 94.0, "product": "COC1=CC=C2C=C(NC2=C1)C=CC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 6-methoxyindole-2-carboxaldehyde (145) with benzyltriphenylphosphonium bromide using the procedure described in example 37 gave (146) (94%) as a white solid (mixture of E/Z isomers) which was used without further purification.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccc2[nH]ccc2c1.c1ccccc1 | HO- | null | null | null | COc1ccc2cc(C=O)[nH]c2c1.c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>>COc1ccc2cc(C=Cc3ccccc3)[nH]c2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-48da5ed2f8704646a3a54504d181f110 | N#CCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O.[CH3][Sn]([CH3])([CH3])[N]=[N+]=[N-].[CH3][Sn]([CH3])([CH3])[N]=[N+]=[N-]>>O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCc1nnn[nH]1 | ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC#N.N(=[N+]=[N-])[Sn](C)(C)C.N(=[N+]=[N-])[Sn](C)(C)C>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC2=NN=NN2 | [O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[Cl:15])[cH:16][c:17]1[c:18]2[c:19]2[cH:20][c:21]([OH:22])[cH:23][cH:24][c:25]2[n:26]1[CH2:27][CH2:28][C:29]#[N:30].[CH3][Sn]([CH3])([CH3])[N:33]=[N+]=[N-].[CH3][Sn]([CH3])([CH3])[N:32]=[N+:31]=[N-]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5... | N#CCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O.[CH3][Sn]([CH3])([CH3])[N]=[N+]=[N-].[CH3][Sn]([CH3])([CH3])[N]=[N+]=[N-] | O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCc1nnn[nH]1 | null | null | O.C(C)(=O)OCC.C1(=CC=CC=C1)C.CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | 646c410a4d640a8a98513ee566d2532f14933769e7f019fbcabb087b4a016a35 | d6a8817f429c74ff8b90214ce1b775ad05560db3c4a19d34769a0ffcc4046a33 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2ccccc2n1CCc1nnn[nH]1 | [CH3]-[Sn](-[CH3])(-[CH3])-[N;H0;D2;+0:1]=[N+;H0;D2:2]=[N-].[CH3]-[Sn](-[CH3])(-[CH3])-[N;H0;D2;+0:3]=[N+]=[N-].[C:4]-[C:5]-[C;H0;D2;+0:6]#[N;H0;D1;+0:7]>>[C:4]-[C:5]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:7]:[n;H0;D2;+0:2]:[n;H0;D2;+0:1]:[nH;D2;+0:3]:1 | 72.2 | [{"value": 72.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC2=NN=NN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.2, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(NC2=O)=O)O)CCC2=NN=NN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of nitrile (238) (0.68 g, 1.63 mmol) prepared as described in example 98 in toluene/dimethylformamide (5:1, 120 mL) was added azidotrimethyl tin (0.67 g, 3.26 mmol). The resulting solution was heated at reflux for 24 hours before a further portion of azidotrimethyl tin (0.34 g, 1.63 mmol) was added. After... | 10.6084/m9.figshare.5104873.v1 | null | Azide.Azide.Nitrile.Tin.Tin | null | null | c1nnn[nH]1 | c1ccccc1.c1nnn[nH]1.C1NCc2c1ccc1nc3ccccc3c21 | Sn | O.C(C)(=O)OCC.C1(=CC=CC=C1)C.CN(C=O)C | null | null | N#CCCn1c2ccc(O)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)NC3=O.[CH3][Sn]([CH3])([CH3])[N]=[N+]=[N-].[CH3][Sn]([CH3])([CH3])[N]=[N+]=[N-]>O.C(C)(=O)OCC.C1(=CC=CC=C1)C.CN(C=O)C>O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1c2c2cc(O)ccc2n1CCc1nnn[nH]1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5ff531db69c462a869d3c4a2037c1a7 | COCC(O)Cn1c2ccc(OC)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O>>O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CC(O)CO | OC(CN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)OC)COC>>OC(CN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O)CO | C[O:21][c:20]1[cH:19][c:18]2[c:17]3[c:6]4[c:7]([c:8](-[c:9]5[cH:10][cH:11][cH:12][cH:13][cH:14]5)[cH:15][c:16]3[n:25]([CH2:26][CH:27]([OH:28])[CH2:29][O:30]C)[c:24]2[cH:23][cH:22]1)[C:2](=[O:1])[NH:3][C:4]4=[O:5]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[cH:15][c:16]... | COCC(O)Cn1c2ccc(OC)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O | O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CC(O)CO | null | null | C(C)(=O)OCC.CCCCCC | Deprotection | OtherReaction | 4d6c8edd9fbb24fe93d1708ee72ea6d7f9f2ced9255486c584465734072583b3 | 0019c7eff1b5e27bd389d7453db70f02f82e6eb53fc11519e24abebafecd8503 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[C:2]-[C:3].C-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[OH;D1;+0:1].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7] | 31.6 | [{"value": 31.0, "product": "OC(CN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.6, "product": "OC(CN1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=CC=CC=C1)C(NC3=O)=O)O)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Demethylation of alcohol (225) (96 mg, 0.22 mmol) prepared as described in example 290 employing the procedure described in example 80 was followed by chromatography on silica eluting with ethyl acetate/hexane (4:1). Crystallisation from ethyl acetate/hexane gave phenol (226) (28 mg, 31%) as an orange/yellow powder, mp... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Primary alcohol.Aromatic alcohol | null | null | c1ccccc1.C1NCc2c1ccc1nc3ccccc3c21 | Other | C(C)(=O)OCC.CCCCCC | null | null | COCC(O)Cn1c2ccc(OC)cc2c2c3c(c(-c4ccccc4)cc21)C(=O)NC3=O>C(C)(=O)OCC.CCCCCC>O=C1NC(=O)c2c1c(-c1ccccc1)cc1c2c2cc(O)ccc2n1CC(O)CO |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-18531f62cf63405188edd0bdbe1ede32 | COc1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1.O=C1C=CC(=O)O1>>COc1ccc2[nH]c3c(c2c1)C1C(=O)OC(=O)C1C(c1ccccc1Cl)C3 | ClC1=C(C=CC=C1)C=CC=1NC2=CC=C(C=C2C1)OC.C1(\C=C/C(=O)O1)=O>>ClC1=C(C=CC=C1)C1CC=2NC=3C=CC(=CC3C2C2C1C(OC2=O)=O)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]([CH:27]=[CH:19][c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3[Cl:26])[cH:9][c:10]2[cH:11]1.[CH:12]1=[CH:18][C:16](=[O:17])[O:15][C:13]1=[O:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[c:9]([c:10]2[cH:11]1)[CH:12]1[C:13](=[O:14])[O:15][C:16](=[O:17])[CH:18]1[CH:19]([c... | COc1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1.O=C1C=CC(=O)O1 | COc1ccc2[nH]c3c(c2c1)C1C(=O)OC(=O)C1C(c1ccccc1Cl)C3 | null | null | C=1(C(=CC=CC1)C)C | C-C Coupling | OtherReaction | e32df616349e641e98b0cb04d918a2f1c5ea561df38c6152b2e7436c0d681d1b | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | O=C1OC(=O)C2C(c3ccccc3)Cc3[nH]c4ccccc4c3C12 | [O;D1;H0:1]=[C:2]1-[#8:3]-[C:4](=[O;D1;H0:5])-[CH;D2;+0:6]=[CH;D2;+0:7]-1.[c:8]:[c:9]1:[cH;D2;+0:10]:[c:11](-[CH;D2;+0:12]=[CH;D2;+0:13]-[c:14](:[c:15]):[c:16]):[#7;a:17]:[c:18]:1:[c:19]>>[O;D1;H0:1]=[C:2]1-[#8:3]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:6]2-[CH;D3;+0:7]-1-[c;H0;D3;+0:10]1:[c:9](:[c:8]):[c:18](:[c:19]):[#7;a:17]:... | null | [] | null | null | null | null | A solution of trans-diene (27) (0.30 g, 1.06 mmol) prepared as described in example 37 and maleic anhydride (0.16 g, 1.59 mmol) in xylene (30 mL) were heated at reflux for 18 hours, before being concentrated in vacuo and chromatographed on silica eluting with ethyl acetatelhexane (1:2). Crystallisation from ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccc2[nH]ccc2c1.C1=CCOC1 | c1ccc2c3c([nH]c2c1)CCC1COCC31 | c1ccccc1.c1ccc2c3c([nH]c2c1)CCC1COCC31 | null | C=1(C(=CC=CC1)C)C | null | null | COc1ccc2[nH]c(C=Cc3ccccc3Cl)cc2c1.O=C1C=CC(=O)O1>C=1(C(=CC=CC1)C)C>COc1ccc2[nH]c3c(c2c1)C1C(=O)OC(=O)C1C(c1ccccc1Cl)C3 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-425a6fdd79984f919dc2fb2de7f6baed | COc1ccc(CN)c(OC)c1.COc1ccc2[nH]c3c(c2c1)C1C(=O)OC(=O)C1C(c1ccccc1Cl)C3>>COc1ccc(CN2C(=O)c3c(-c4ccccc4Cl)cc4[nH]c5ccc(OC)cc5c4c3C2=O)c(OC)c1 | ClC1=C(C=CC=C1)C1CC=2NC=3C=CC(=CC3C2C2C1C(OC2=O)=O)OC.COC1=C(CN)C=CC(=C1)OC>>ClC1=C(C=CC=C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(N(C2=O)CC2=C(C=C(C=C2)OC)OC)=O)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH2:8])[c:35]([O:36][CH3:37])[cH:38]1.O1[C:9](=[O:10])[CH:11]2[CH:12]([c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[Cl:19])[CH2:20][c:21]3[nH:22][c:23]4[cH:24][cH:25][c:26]([O:27][CH3:28])[cH:29][c:30]4[c:31]3[CH:32]2[C:33]1=[O:34]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:... | COc1ccc(CN)c(OC)c1.COc1ccc2[nH]c3c(c2c1)C1C(=O)OC(=O)C1C(c1ccccc1Cl)C3 | COc1ccc(CN2C(=O)c3c(-c4ccccc4Cl)cc4[nH]c5ccc(OC)cc5c4c3C2=O)c(OC)c1 | null | null | C(C)(=O)O | Acylation | OtherReaction | 73046fde7b0f6328edcfd588f5c2e038ff2cc300c7e42ea70f46d7d4fe40722f | 2a4a20e639c386292668b0b265a8e1b50d707d5f0576437dc5ade3e7fd444d29 | O=C1c2c(-c3ccccc3)cc3[nH]c4ccccc4c3c2C(=O)N1Cc1ccccc1 | [Cl;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[c:7]2:[#7;a:8]:[c:9]:[c:10]:[c:11]:2-[CH;D3;+0:12]2-[C;H0;D3;+0:13](=[O;D1;H0:14])-O-[C;H0;D3;+0:15](=[O;D1;H0:16])-[CH;D3;+0:17]-1-2):[c:18]:[c:19].[NH2;D1;+0:20]-[C:21]-[c:22]>>[Cl;D1;H0:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:5]1:[cH;D2;+0:... | null | [] | null | null | null | null | To a solution of anhydride (286) (2.80 g, 7.42 mmol) prepared as described in example 296 in glacial acetic acid (70 mL) was added 2,4-dimethoxybenzylamine (1.67 mL, 11.1 mmol). The resulting solution was heated at reflux for 6 hours before being partially concentrated under reduced pressure and diluted with water to p... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Substituted dicarboximide | c1ccc2c3c([nH]c2c1)CCC1COCC31 | c1ccc2c(c1)nc1ccc3c(c12)C[N]C3 | c1ccccc1.c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)C[N]C3 | HO- | C(C)(=O)O | null | null | COc1ccc(CN)c(OC)c1.COc1ccc2[nH]c3c(c2c1)C1C(=O)OC(=O)C1C(c1ccccc1Cl)C3>C(C)(=O)O>COc1ccc(CN2C(=O)c3c(-c4ccccc4Cl)cc4[nH]c5ccc(OC)cc5c4c3C2=O)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fd3a31722eab4427bb653cfb10123b6e | C=CCBr.COc1ccc(CN2C(=O)c3c(-c4ccccc4Cl)cc4[nH]c5ccc(OC)cc5c4c3C2=O)c(OC)c1>>C=CCn1c2ccc(OC)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)N(Cc1ccc(OC)cc1OC)C3=O | ClC1=C(C=CC=C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(N(C2=O)CC2=C(C=C(C=C2)OC)OC)=O)OC.C([O-])([O-])=O.[K+].[K+].C(C=C)Br>>C(C=C)N1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)Cl)C(N(C3=O)CC3=C(C=C(C=C3)OC)OC)=O)OC | Br[CH2:3][CH:2]=[CH2:1].[nH:4]1[c:5]2[cH:6][cH:7][c:8]([O:9][CH3:10])[cH:11][c:12]2[c:13]2[c:14]3[c:15]([c:16](-[c:17]4[cH:18][cH:19][cH:20][cH:21][c:22]4[Cl:23])[cH:24][c:25]12)[C:26](=[O:27])[N:28]([CH2:29][c:30]1[cH:31][cH:32][c:33]([O:34][CH3:35])[cH:36][c:37]1[O:38][CH3:39])[C:40]3=[O:41]>>[CH2:1]=[CH:2][CH2:3][n:... | C=CCBr.COc1ccc(CN2C(=O)c3c(-c4ccccc4Cl)cc4[nH]c5ccc(OC)cc5c4c3C2=O)c(OC)c1 | C=CCn1c2ccc(OC)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)N(Cc1ccc(OC)cc1OC)C3=O | null | null | C(C)(=O)OCC.O.CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | cddce2a874664e470793fc9c2c3968cab03ff58e8d853d30fd6a8d30bc88b7bf | 4c606dc54eac846ef90c7b3255999ceff93277747e7c2b0ddd37ccf25562b7c5 | O=C1c2c(-c3ccccc3)cc3[nH]c4ccccc4c3c2C(=O)N1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]=[C;D1;H2:3].[c:4]:[c:5]1:[c:6]:[c:7]:[c:8](:[c:9]):[nH;D2;+0:10]:1>>[C;D1;H2:3]=[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[c:5](:[c:4]):[c:6]:[c:7]:[c:8]:1:[c:9] | 57 | [{"value": 57.0, "product": "C(C=C)N1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)Cl)C(N(C3=O)CC3=C(C=C(C=C3)OC)OC)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.7, "product": "C(C=C)N1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)Cl)C(N(C3=O)CC3=C(C=C(C=C3)OC)OC)=O)OC", "details": "CALCULATEDPERCENTYIELD... | 90 | CELSIUS | 3 | HOUR | To a solution of carbazole (287) (150 mg, 0.28 mmol) prepared as described in example 297 in dimethylformamide (10 mL) under nitrogen was added potassium carbonate (0.39 g, 2.80 mmol) and allyl bromide (720L, 0.84 mmol). The resulting suspension was warmed to 90° C. with stirring for 3 hours before being diluted with w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Allyl | Allyl | c1ccc2c(c1)[nH]c1ccc3c(c12)C[NH]C3 | C1NCc2c1ccc1[nH]c3ccccc3c21 | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21.c1ccccc1 | HBr | C(C)(=O)OCC.O.CN(C=O)C | 90 | 3 | C=CCBr.COc1ccc(CN2C(=O)c3c(-c4ccccc4Cl)cc4[nH]c5ccc(OC)cc5c4c3C2=O)c(OC)c1>C(C)(=O)OCC.O.CN(C=O)C>C=CCn1c2ccc(OC)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)N(Cc1ccc(OC)cc1OC)C3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-600ccf5b9b9540ba9a97d77d8ba42995 | C=CCCBr.COc1ccc(CN2C(=O)c3c(-c4ccccc4Cl)cc4[nH]c5ccc(OC)cc5c4c3C2=O)c(OC)c1>>C=CCCn1c2ccc(OC)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)N(Cc1ccc(OC)cc1OC)C3=O | ClC1=C(C=CC=C1)C1=CC=2NC=3C=CC(=CC3C2C2=C1C(N(C2=O)CC2=C(C=C(C=C2)OC)OC)=O)OC.BrCCC=C>>C(CC=C)N1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)Cl)C(N(C3=O)CC3=C(C=C(C=C3)OC)OC)=O)OC | Br[CH2:4][CH2:3][CH:2]=[CH2:1].[nH:5]1[c:6]2[cH:7][cH:8][c:9]([O:10][CH3:11])[cH:12][c:13]2[c:14]2[c:15]3[c:16]([c:17](-[c:18]4[cH:19][cH:20][cH:21][cH:22][c:23]4[Cl:24])[cH:25][c:26]12)[C:27](=[O:28])[N:29]([CH2:30][c:31]1[cH:32][cH:33][c:34]([O:35][CH3:36])[cH:37][c:38]1[O:39][CH3:40])[C:41]3=[O:42]>>[CH2:1]=[CH:2][C... | C=CCCBr.COc1ccc(CN2C(=O)c3c(-c4ccccc4Cl)cc4[nH]c5ccc(OC)cc5c4c3C2=O)c(OC)c1 | C=CCCn1c2ccc(OC)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)N(Cc1ccc(OC)cc1OC)C3=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 9fdb054f006790672a590a47d7107803946a0e4d83da9b5f9c5cc6110c56f155 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C1c2c(-c3ccccc3)cc3[nH]c4ccccc4c3c2C(=O)N1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]=[C;D1;H2:4].[c:5]:[c:6]1:[c:7]:[c:8]:[c:9](:[c:10]):[nH;D2;+0:11]:1>>[C;D1;H2:4]=[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[c:6](:[c:5]):[c:7]:[c:8]:[c:9]:1:[c:10] | 58.4 | [{"value": 58.0, "product": "C(CC=C)N1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)Cl)C(N(C3=O)CC3=C(C=C(C=C3)OC)OC)=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.4, "product": "C(CC=C)N1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)Cl)C(N(C3=O)CC3=C(C=C(C=C3)OC)OC)=O)OC", "details": "CALCULATEDPERCENTYIE... | null | null | null | null | Reaction of carbazole (287) (260 mg, 0.51 mmol) prepared as described in example 297 with 4-bromo-1-butene (155 □L, 1.53 mmol) according to procedure described in example 298 gave carbazole (289) (173 mg, 58%) as a yellow powder, mp 161–164° C. 1H NMR δ [(CD3)2SO] 8.50 (d, J=2.6 Hz, 1H), 7.89 (s, 1H), 7.73 (d, J=9.0 Hz... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1ccc2c(c1)[nH]c1ccc3c(c12)C[NH]C3 | C1NCc2c1ccc1[nH]c3ccccc3c21 | c1ccccc1.C1NCc2c1ccc1[nH]c3ccccc3c21.c1ccccc1 | HBr | null | null | null | C=CCCBr.COc1ccc(CN2C(=O)c3c(-c4ccccc4Cl)cc4[nH]c5ccc(OC)cc5c4c3C2=O)c(OC)c1>>C=CCCn1c2ccc(OC)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)N(Cc1ccc(OC)cc1OC)C3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f5196dcb4161474bbb05e2f36ea37b3b | C=CCn1c2ccc(OC)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)N(Cc1ccc(OC)cc1OC)C3=O.CC(C)=O.O>>COc1ccc(CN2C(=O)c3c(-c4ccccc4Cl)cc4c(c3C2=O)c2cc(OC)ccc2n4CC(O)CO)c(OC)c1 | C(C=C)N1C=2C=CC(=CC2C=2C3=C(C(=CC12)C1=C(C=CC=C1)Cl)C(N(C3=O)CC3=C(C=C(C=C3)OC)OC)=O)OC.C[N+]1(CCOCC1)[O-].CC(=O)C.O>>ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(N(C2=O)CC2=C(C=C(C=C2)OC)OC)=O)OC)CC(CO)O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[C:9](=[O:10])[c:11]3[c:12](-[c:13]4[cH:14][cH:15][cH:16][cH:17][c:18]4[Cl:19])[cH:20][c:21]4[c:22]([c:23]3[C:24]2=[O:25])[c:26]2[cH:27][c:28]([O:29][CH3:30])[cH:31][cH:32][c:33]2[n:34]4[CH2:35][CH:36]=[CH2:38])[c:40]([O:41][CH3:42])[cH:43]1.CC(C)=[O:37].[OH2:39]>>[CH3:1... | C=CCn1c2ccc(OC)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)N(Cc1ccc(OC)cc1OC)C3=O.CC(C)=O.O | COc1ccc(CN2C(=O)c3c(-c4ccccc4Cl)cc4c(c3C2=O)c2cc(OC)ccc2n4CC(O)CO)c(OC)c1 | null | [Os](=O)(=O)(=O)=O | C(C)(=O)OCC.Cl | Heteroatom Alkylation and Arylation | OtherReaction | 345506133277b562461fd4b28175e452202e676c1e8bfb3e7a07c6b5b46eb017 | 940633fa24d9f43cb0ba0036641980eb579ae4284341d810fa2427d9809d0d46 | O=C1c2c(-c3ccccc3)cc3[nH]c4ccccc4c3c2C(=O)N1Cc1ccccc1 | C-C(-C)=[O;H0;D1;+0:1].[#7;a:2]-[C:3]-[CH;D2;+0:4]=[CH2;D1;+0:5].[OH2;D0;+0:6]>>[#7;a:2]-[C:3]-[CH;D3;+0:4](-[OH;D1;+0:1])-[CH2;D2;+0:5]-[OH;D1;+0:6] | 94 | [{"value": 94.0, "product": "ClC1=C(C=CC=C1)C1=CC=2N(C=3C=CC(=CC3C2C2=C1C(N(C2=O)CC2=C(C=C(C=C2)OC)OC)=O)OC)CC(CO)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of carbazole (288) (80 mg, 0.14 mmol) procedure described in example 298 in acetone/water (4:1, 20 mL) was added N-methylmorpholine N-oxide (33 mg, 0.28 mmol) and osmium tetroxide (176 uL, 4% solution in water, ˜0.028 mmol). The reaction mixture was stirred at room temperature for 18 hours before being di... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Allyl | Primary alcohol.Secondary alcohol | null | null | c1ccccc1.c1ccccc1.C1NCc2c1ccc1nc3ccccc3c21 | Other | [Os](=O)(=O)(=O)=O.C(C)(=O)OCC.Cl | null | 18 | C=CCn1c2ccc(OC)cc2c2c3c(c(-c4ccccc4Cl)cc21)C(=O)N(Cc1ccc(OC)cc1OC)C3=O.CC(C)=O.O>[Os](=O)(=O)(=O)=O.C(C)(=O)OCC.Cl>COc1ccc(CN2C(=O)c3c(-c4ccccc4Cl)cc4c(c3C2=O)c2cc(OC)ccc2n4CC(O)CO)c(OC)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8fb542c851a94841addcbc8f675fb840 | CCC[CH2][Sn](/[CH]=C/CCO)([CH2]CCC)[CH2]CCC.COc1cc2c(cc1OS(=O)(=O)C(F)(F)F)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O>>COc1cc2c(cc1/C=C/CCO)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | FC(S(=O)(=O)OC=1C(=CC=2C=3C4=C(C(=CC3NC2C1)C1=C(C=CC=C1)Cl)C(NC4=O)=O)OC)(F)F.C(CCC)[Sn](/C=C/CCO)(CCCC)CCCC.C(C)(=O)OCC.[Cl-].[Li+]>>ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)OC)\C=C\CCO | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)/[CH:9]=[CH:10]/[CH2:11][CH2:12][OH:13].O=S(=O)(O[c:8]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([cH:7]1)[nH:14][c:15]1[cH:16][c:17](-[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[Cl:24])[c:25]3[c:26]([c:27]21)[C:28](=[O:29])[NH:30][C:31]3=[O:32])C(F)(F)F>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH... | CCC[CH2][Sn](/[CH]=C/CCO)([CH2]CCC)[CH2]CCC.COc1cc2c(cc1OS(=O)(=O)C(F)(F)F)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | COc1cc2c(cc1/C=C/CCO)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | 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 | CN(C)C=O | C-C Coupling | Stille reaction_other OTf | 92ab09c73a964c1a0dcd7658e1a44c8859087c25093fbf9ea4d4c014f3f8cadd | 46de4d1253710b3a7d4f46887df51b2ccba46e0a9427959558bd6f96ec8696eb | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)/[CH;D2;+0:1]=[C:2]/[C:3]-[C:4].F-C(-F)(-F)-S(=O)(=O)-O-[c;H0;D3;+0:5]1:[c:6]:[c:7](:[#7;a:8]:[c:9]):[c:10]:[c:11]:[c:12]:1-[#8:13]>>[#8:13]-[c:12]1:[c:11]:[c:10]:[c:7](:[#7;a:8]:[c:9]):[c:6]:[c;H0;D3;+0:5]:1/[CH;D2;+0:1]=[C:2]/[C:3]-[C:4] | 95.9 | [{"value": 95.0, "product": "ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)OC)\\C=C\\CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.9, "product": "ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)OC)\\C=C\\CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the triflate (169) (0.20 g, 0.35 mmol) prepared as described in example 308, (3E)-4-(tributylstannyl)-3-buten-1-ol (0.19 g, 0.53 mmol) and lithium chloride (29 mg, 0.70 mmol) in DMF (10 mL) was purged by bubbling nitrogen through the liquid for 10 min. Bis(triphenylphosphine)palladium dichloride (12 mg, 0... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Tin | null | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | TfOH.HO-.Sn | 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.CN(C)C=O | null | null | CCC[CH2][Sn](/[CH]=C/CCO)([CH2]CCC)[CH2]CCC.COc1cc2c(cc1OS(=O)(=O)C(F)(F)F)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O>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.CN(C)C=O>COc1cc2c(cc1/C=C/CCO)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5fdf3bedfc814e3c8a3029fbf4e6173c | COc1cc2c(cc1/C=C/CCO)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O>>COc1cc2c(cc1CCCCO)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)OC)\C=C\CCO>>ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)OC)CCCCO | [CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1/[CH:9]=[CH:10]/[CH2:11][CH2:12][OH:13])[nH:14][c:15]1[cH:16][c:17](-[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[Cl:24])[c:25]3[c:26]([c:27]21)[C:28](=[O:29])[NH:30][C:31]3=[O:32]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[nH:1... | COc1cc2c(cc1/C=C/CCO)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | COc1cc2c(cc1CCCCO)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | null | O=[Pt]=O | O1CCCC1.CO | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | [#7;a:1]:[c:2]:[c:3]:[c:4](/[CH;D2;+0:5]=[CH;D2;+0:6]/[C:7]-[C:8]):[c:9]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[C:7]-[C:8]):[c:9] | 135 | [{"value": 100.0, "product": "ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)OC)CCCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 135.0, "product": "ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)OC)CCCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of (170) (0.15 g, 0.33 mmol) prepared as described in example 309 and PtO2 (20 mg) in 1:1 tetrahydrofuran/methanol (30 mL) was shaken under an atmosphere of hydrogen gas at 40 psi pressure for 30 min. The catalyst was removed by filtration through Celite, washing through with more solvent. The combined filtra... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | null | O=[Pt]=O.O1CCCC1.CO | null | 0.5 | COc1cc2c(cc1/C=C/CCO)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O>O=[Pt]=O.O1CCCC1.CO>COc1cc2c(cc1CCCCO)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aadb4706b7a04a7f8223ac521ce2756f | COc1cc2c(cc1CCCCOS(=O)(=O)C(F)(F)F)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O.[I-]>>COc1cc2c(cc1CCCCI)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | FC(S(=O)(=O)OCCCCC=1C(=CC=2C=3C4=C(C(=CC3NC2C1)C1=C(C=CC=C1)Cl)C(NC4=O)=O)OC)(F)F.[I-].[Na+]>>ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)OC)CCCCI | O=S(=O)(O[CH2:12][CH2:11][CH2:10][CH2:9][c:8]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([cH:7]1)[nH:14][c:15]1[cH:16][c:17](-[c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[Cl:24])[c:25]3[c:26]([c:27]21)[C:28](=[O:29])[NH:30][C:31]3=[O:32])C(F)(F)F.[I-:13]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[CH2:9][CH2:10][CH2:11][... | COc1cc2c(cc1CCCCOS(=O)(=O)C(F)(F)F)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O.[I-] | COc1cc2c(cc1CCCCI)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | null | null | C(C)(=O)OCC | Functional Group Interconversion | OtherReaction | 8c25114f6e35a2eaed073de14ecf22ab2f1e189db18bca7f82e8c0b93444a0b1 | 23ab3c443e9999f7cd1707e344529116afaee675d7ed2bc5da5c5c7516fe5ad6 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | F-C(-F)(-F)-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[C:3].[I-;H0;D0:4]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:4] | null | [] | null | null | null | null | A mixture of the mesylate (172) 0.12 g, 0.21 mmol) prepared as described in example 311 and sodium iodide (1 g) in ethyl acetate (50 mL) was refluxed for 4 h. The cooled solution was washed with water and worked up to give the iodide (173) which crystallised from tetrahydrofuran/petroleum ether as an orange powder (0.1... | 10.6084/m9.figshare.5104873.v1 | null | Triflate | Primary halide | null | null | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | TfOH | C(C)(=O)OCC | null | null | COc1cc2c(cc1CCCCOS(=O)(=O)C(F)(F)F)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O.[I-]>C(C)(=O)OCC>COc1cc2c(cc1CCCCI)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ef93ac7314bc40abb94057164ba9666f | CNC.COc1cc2c(cc1CCCCI)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O>>COc1cc2c(cc1CCCCN(C)C)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)OC)CCCCI.CNC.COC1=CC=2C=3C4=C(C(=CC3NC2C=C1)C(=O)OCC1=CC=CC=C1)C(NC4=O)=O>>ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)OC)CCCCN(C)C | [NH:13]([CH3:14])[CH3:15].I[CH2:12][CH2:11][CH2:10][CH2:9][c:8]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([cH:7]1)[nH:16][c:17]1[cH:18][c:19](-[c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3[Cl:26])[c:27]3[c:28]([c:29]21)[C:30](=[O:31])[NH:32][C:33]3=[O:34]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[CH2:9][CH2:10][CH2:11]... | CNC.COc1cc2c(cc1CCCCI)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | COc1cc2c(cc1CCCCN(C)C)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[NH;D2;+0:5]-[C;D1;H3:6]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:5](-[C;D1;H3:4])-[C;D1;H3:6] | 64 | [{"value": 64.0, "product": "ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)OC)CCCCN(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | Reaction of the iodide (173) prepared as described in example 312 with aqueous dimethylamine using the procedure described in example 179 of Scheme 3 except that the reaction conditions were 6 h at room temperature gave (174) (64%) as an orange powder, mp 162–164° C. 1H NMR δ [(CD3)2SO] 11.85 (s, 1H), 11.04 (br s, 1H),... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HI | null | null | 6 | CNC.COc1cc2c(cc1CCCCI)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O>>COc1cc2c(cc1CCCCN(C)C)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-53b8de3adf874b74b5aac8d0effc825e | C1CCNC1.COc1cc2c(cc1CCCCI)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O>>COc1cc2c(cc1CCCCN1CCCC1)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)OC)CCCCI.N1CCCC1>>ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)OC)CCCCN2CCCC2 | [NH:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1.I[CH2:12][CH2:11][CH2:10][CH2:9][c:8]1[c:3]([O:2][CH3:1])[cH:4][c:5]2[c:6]([cH:7]1)[nH:18][c:19]1[cH:20][c:21](-[c:22]3[cH:23][cH:24][cH:25][cH:26][c:27]3[Cl:28])[c:29]3[c:30]([c:31]21)[C:32](=[O:33])[NH:34][C:35]3=[O:36]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[CH2:9]... | C1CCNC1.COc1cc2c(cc1CCCCI)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | COc1cc2c(cc1CCCCN1CCCC1)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 19b442dc26882f89f7423416f5e0a16bdb8e48776df57991434a0634e21f0505 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3cc(CCCCN4CCCC4)ccc3c21 | I-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]1-[C:5]-[C:6]-[C:7]-[NH;D2;+0:8]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:4]-[C:5]-[C:6]-[C:7]-1 | 75 | [{"value": 75.0, "product": "ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)OC)CCCCN2CCCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Reaction of the iodide (173) prepared as described in example 312 with pyrrolidine using the procedure described in example 179 except that the reaction conditions were 2 h at room temperature gave (176) (75%) as an orange powder, which was used without further purification, mp 173–178° C. 1H NMR δ [(CD3)2SO] 11.85 (s,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | HI | null | null | 2 | C1CCNC1.COc1cc2c(cc1CCCCI)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O>>COc1cc2c(cc1CCCCN1CCCC1)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b586723b61704dd28d0ecfa2f449896d | COc1cc2c(cc1CCCCI)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O.c1ccncc1>>O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1[nH]c3cc(CCCCN4CCCC4)c(O)cc3c21 | ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)OC)CCCCI.Cl.N1=CC=CC=C1>>ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)O)CCCCN2CCCC2 | C[O:32][c:31]1[c:21]([CH2:22][CH2:23][CH2:24][CH2:25]I)[cH:20][c:19]2[nH:18][c:17]3[cH:16][c:8](-[c:9]4[cH:10][cH:11][cH:12][cH:13][c:14]4[Cl:15])[c:7]4[c:6]([c:35]3[c:34]2[cH:33]1)[C:4](=[O:5])[NH:3][C:2]4=[O:1].c1[cH:27][n:26][cH:30][cH:29][cH:28]1>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:1... | COc1cc2c(cc1CCCCI)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O.c1ccncc1 | O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1[nH]c3cc(CCCCN4CCCC4)c(O)cc3c21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 760b5eb134d6142f83c23e3407807f09fd7b138480e051dfde75d5bffde6bfc8 | ed5750d8347e51bbb07e9a534b79c99e3dfd7c53478405edf0f6196ff85f5d14 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3cc(CCCCN4CCCC4)ccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4].I-[CH2;D2;+0:5]-[C:6]-[C:7].[cH;D2;+0:8]1:[n;H0;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:[cH;D2;+0:12]:c:1>>[C:7]-[C:6]-[CH2;D2;+0:5]-[N;H0;D3;+0:9]1-[CH2;D2;+0:8]-[CH2;D2;+0:12]-[CH2;D2;+0:11]-[CH2;D2;+0:10]-1.[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 72 | [{"value": 72.0, "product": "ClC1=C(C=CC=C1)C1=CC=2NC=3C=C(C(=CC3C2C2=C1C(NC2=O)=O)O)CCCCN2CCCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Demethylation of (173) prepared as described in example 312 with pyridine hydrochloride using the procedure described in example 81 gave (177) (72%). 1H NMR δ [(CD3)2SO] 11.70 (s, 1H), 10.98 (br s, 1H), 9.30 (br, 1H), 8.31 (s, 1H), 7.57 (dd, J=8.0, 2.2 Hz, 1H), 7.49 (s, 1H), 7.49–7.40 (m, 3H), 7.32 (s, 1H), 2.73 (t, J=... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether | Aromatic alcohol.Tertiary amine | c1ccncc1 | C1CC[NH]C1 | c1ccccc1.c1ccc2c(c1)nc1ccc3c(c12)CNC3.C1CC[NH]C1 | I- | null | null | null | COc1cc2c(cc1CCCCI)[nH]c1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O.c1ccncc1>>O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1[nH]c3cc(CCCCN4CCCC4)c(O)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0431b74d082947e191c50707609c9568 | COc1ccc2sc3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O>>O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1sc3ccc(O)cc3c21 | ClC1=C(C=CC=C1)C1=CC2=C(C=3C(NC(C13)=O)=O)C1=C(S2)C=CC(=C1)OC.B(Br)(Br)Br>>ClC1=C(C=CC=C1)C1=CC2=C(C=3C(NC(C13)=O)=O)C1=C(S2)C=CC(=C1)O | C[O:23][c:22]1[cH:21][cH:20][c:19]2[s:18][c:17]3[cH:16][c:8](-[c:9]4[cH:10][cH:11][cH:12][cH:13][c:14]4[Cl:15])[c:7]4[c:6]([c:26]3[c:25]2[cH:24]1)[C:4](=[O:5])[NH:3][C:2]4=[O:1]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[c:8](-[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[Cl:15])[cH:16][c:17]1[s:18][c:19]3[cH:20][cH:21][... | COc1ccc2sc3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O | O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1sc3ccc(O)cc3c21 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1sc3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 65 | [{"value": 65.0, "product": "ClC1=C(C=CC=C1)C1=CC2=C(C=3C(NC(C13)=O)=O)C1=C(S2)C=CC(=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | Demethylation of (839) prepared as described in example 374 with BBr3 using the procedure described in example 80 except that the reaction time was 48 h gave (840) (65%) as a yellow solid, mp 311–313° C. 1H NMR δ [(CD3)2SO] 11.42 (s, 1H), 9.85 (s, 1H), 9.17 (d, J=2.5 Hz, 1H), 8.32 (s, 1H), 7.9 (d, J=9 Hz, 1H), 7.62 (m,... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)sc1ccc3c(c12)CNC3 | Other | null | null | 48 | COc1ccc2sc3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O>>O=C1NC(=O)c2c1c(-c1ccccc1Cl)cc1sc3ccc(O)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-449db22805af466fa07da83d9037e83d | CNC.COc1cc2c(cc1OCCCBr)oc1cc(-c3ccccc3Cl)c3c(c12)C(=O)N(CCCBr)C3=O>>COc1cc2c(cc1OCCCN(C)C)oc1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | BrCCCOC1=CC2=C(C=C1OC)C=1C=3C(N(C(C3C(=CC1O2)C2=C(C=CC=C2)Cl)=O)CCCBr)=O.CNC>>ClC1=C(C=CC=C1)C1=CC2=C(C=3C(NC(C13)=O)=O)C1=C(O2)C=C(C(=C1)OC)OCCCN(C)C | [NH:13]([CH3:14])[CH3:15].BrCCC[N:32]1[C:30](=[O:31])[c:28]2[c:27]([c:19](-[c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3[Cl:26])[cH:18][c:17]3[o:16][c:6]4[c:5]([cH:4][c:3]([O:2][CH3:1])[c:8]([O:9][CH2:10][CH2:11][CH2:12]Br)[cH:7]4)[c:29]32)[C:33]1=[O:34]>>[CH3:1][O:2][c:3]1[cH:4][c:5]2[c:6]([cH:7][c:8]1[O:9][CH2:10][CH2:1... | CNC.COc1cc2c(cc1OCCCBr)oc1cc(-c3ccccc3Cl)c3c(c12)C(=O)N(CCCBr)C3=O | COc1cc2c(cc1OCCCN(C)C)oc1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 9a0cf426a88195917c644236d546ba744ba1149b5402e9c014f57ccddc78a4d1 | 8531a87128925ee84243b99e24583b0bc2fc05e7364ed3178245a169d9fe2986 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1oc3ccccc3c21 | Br-C-C-C-[N;H0;D3;+0:1]1-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]-[C:6]-1=[O;D1;H0:7].Br-[CH2;D2;+0:8]-[C:9]-[C:10].[C;D1;H3:11]-[NH;D2;+0:12]-[C;D1;H3:13]>>[C:10]-[C:9]-[CH2;D2;+0:8]-[N;H0;D3;+0:12](-[C;D1;H3:11])-[C;D1;H3:13].[O;D1;H0:3]=[C:2]1-[NH;D2;+0:1]-[C:6](=[O;D1;H0:7])-[c:5]:[c:4]-1 | 84 | [{"value": 84.0, "product": "ClC1=C(C=CC=C1)C1=CC2=C(C=3C(NC(C13)=O)=O)C1=C(O2)C=C(C(=C1)OC)OCCCN(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | Reaction of dibromide (331) (100 mg, 0.16 mmol) prepared as described in example 385 with aqueous dimethylamine solution (40%, 5.0 mL) according to The procedure described in example 179, except that the reaction was performed in tetrahydrofuran (50 mL) at room temperature for 30 hours, gave the crude diamine (LXXX; Ar... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Substituted dicarboximide.Secondary amine | Unsubstituted dicarboximide.Tertiary amine | c1ccc2c(c1)oc1ccc3c(c12)C[NH]C3 | c1ccc2c(c1)oc1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)oc1ccc3c(c12)CNC3 | HBr | O1CCCC1 | null | 24 | CNC.COc1cc2c(cc1OCCCBr)oc1cc(-c3ccccc3Cl)c3c(c12)C(=O)N(CCCBr)C3=O>O1CCCC1>COc1cc2c(cc1OCCCN(C)C)oc1cc(-c3ccccc3Cl)c3c(c12)C(=O)NC3=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5a7efcaac9d44119a09dedaf3e502208 | COc1ccc2[nH]c3c(C)c(-c4ccccc4)c4c(c3c2c1)C(=O)NC4=O>>Cc1c(-c2ccccc2)c2c(c3c1[nH]c1ccc(O)cc13)C(=O)NC2=O | COC1=CC=2C=3C4=C(C(=C(C3NC2C=C1)C)C1=CC=CC=C1)C(NC4=O)=O.B(Br)(Br)Br>>OC1=CC=2C=3C4=C(C(=C(C3NC2C=C1)C)C1=CC=CC=C1)C(NC4=O)=O | C[O:19][c:18]1[cH:17][cH:16][c:15]2[nH:14][c:13]3[c:2]([CH3:1])[c:3](-[c:4]4[cH:5][cH:6][cH:7][cH:8][cH:9]4)[c:10]4[c:11]([c:12]3[c:21]2[cH:20]1)[C:22](=[O:23])[NH:24][C:25]4=[O:26]>>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[c:10]2[c:11]([c:12]3[c:13]1[nH:14][c:15]1[cH:16][cH:17][c:18]([OH:19])[cH:20][... | COc1ccc2[nH]c3c(C)c(-c4ccccc4)c4c(c3c2c1)C(=O)NC4=O | Cc1c(-c2ccccc2)c2c(c3c1[nH]c1ccc(O)cc13)C(=O)NC2=O | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1c(-c1ccccc1)cc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 90 | [{"value": 90.0, "product": "OC1=CC=2C=3C4=C(C(=C(C3NC2C=C1)C)C1=CC=CC=C1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Demethylation of (803) prepared as described in example 406 with BBr3 using the procedure described in example 69 gave (804) (90%), mp 270–280° C. 1H NMR δ [(CD3)2SO] 11.60 (s, 1H), 10.82 (s, 1H), 9.22 (s, 1H), 8.31 (d, J=2.0 Hz, 1H), 7.47–7.42 (m, 4H), 7.36–7.23 (m, 2H), 7.06 (dd, J=8.7, 2.0 Hz, 1H), 2.32 (s, 3H). EIM... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | Other | null | null | null | COc1ccc2[nH]c3c(C)c(-c4ccccc4)c4c(c3c2c1)C(=O)NC4=O>>Cc1c(-c2ccccc2)c2c(c3c1[nH]c1ccc(O)cc13)C(=O)NC2=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9bcf57638ec4461986b37612b541e68c | COc1ccc2[nH]c(C=O)cc2c1.[Br][Mg][c]1ccccc1>>COc1ccc2[nH]c(C(=O)c3ccccc3)cc2c1 | COC=1C=C2C=C(NC2=CC1)C=O.C1(=CC=CC=C1)[Mg]Br>>COC=1C=C2C=C(NC2=CC1)C(=O)C1=CC=CC=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]([CH:9]=[O:10])[cH:17][c:18]2[cH:19]1.[Br][Mg][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]([C:9](=[O:10])[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][c:18]2[cH:19]1 | COc1ccc2[nH]c(C=O)cc2c1.[Br][Mg][c]1ccccc1 | COc1ccc2[nH]c(C(=O)c3ccccc3)cc2c1 | null | null | null | C-C Coupling | OtherReaction | 813a2aef5e31d204b1b98b796e22e80eaacaf5654877ef9187d7a6f9ad0ac4fe | 7db11402b2132cd2d08e947c3439b66a3e13f302984dbd7579c68a04c5d289a9 | O=C(c1ccccc1)c1cc2ccccc2[nH]1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;D1;H0:6]=[CH;D2;+0:7]-[c:8](:[c:9]):[#7;a:10]:[c:11]>>[O;D1;H0:6]=[C;H0;D3;+0:7](-[c:8](:[c:9]):[#7;a:10]:[c:11])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 91 | [{"value": 91.0, "product": "COC=1C=C2C=C(NC2=CC1)C(=O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of 5-methoxy-1H-indole-2-carbaldehyde with phenylmagnesium bromide using the procedure described in example 404 gave (805) (91%), mp 159–161° C. 1H NMR δ [(CD3)2SO] 11.86 (s, 1H), 7.94–7.91 (m, 2H), 7.71–7.66 (m, 1H), 7.61–7.57 (m, 2H), 7.42 (d, J=8.9 Hz, 1H), 7.16 (d, J=2.4 Hz, 1H), 7.03 (s, 1H), 6.99 (dd, J=... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aldehyde | Ketone | c1ccccc1 | c1ccccc1 | c1ccc2[nH]ccc2c1.c1ccccc1 | HBr.Mg | null | null | null | COc1ccc2[nH]c(C=O)cc2c1.[Br][Mg][c]1ccccc1>>COc1ccc2[nH]c(C(=O)c3ccccc3)cc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5b1bf34dd4f9437a87340eb2f2be19a6 | COc1ccc2[nH]c3ccc4c(c3c2c1)C(=O)NC4=O>>O=C1NC(=O)c2c1ccc1[nH]c3ccc(O)cc3c21 | COC1=CC=2C=3C4=C(C=CC3NC2C=C1)C(NC4=O)=O.B(Br)(Br)Br>>OC1=CC=2C=3C4=C(C=CC3NC2C=C1)C(NC4=O)=O | C[O:16][c:15]1[cH:14][cH:13][c:12]2[nH:11][c:10]3[cH:9][cH:8][c:7]4[c:6]([c:19]3[c:18]2[cH:17]1)[C:4](=[O:5])[NH:3][C:2]4=[O:1]>>[O:1]=[C:2]1[NH:3][C:4](=[O:5])[c:6]2[c:7]1[cH:8][cH:9][c:10]1[nH:11][c:12]3[cH:13][cH:14][c:15]([OH:16])[cH:17][c:18]3[c:19]21 | COc1ccc2[nH]c3ccc4c(c3c2c1)C(=O)NC4=O | O=C1NC(=O)c2c1ccc1[nH]c3ccc(O)cc3c21 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C1NC(=O)c2c1ccc1[nH]c3ccccc3c21 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 79 | [{"value": 79.0, "product": "OC1=CC=2C=3C4=C(C=CC3NC2C=C1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Demethylation of (816) prepared as described in example 416 with BBr3 using the procedure described in example 80 gave (817) (79%), mp 335–345° C. 1H NMR δ [(CD3)2SO] 11.77 (s, 1H), 11.04 (s, 1H), 9.23 (s, 1H), 8.24 (d, J=2.3 Hz, 1H), 7.75 (2d, J=8.2 Hz, 2H), 7.43 (d, J=8.7 Hz, 1H), 7.05 (dd, J=8.7, 2.3 Hz, 1H). Found:... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2c(c1)nc1ccc3c(c12)CNC3 | Other | null | null | null | COc1ccc2[nH]c3ccc4c(c3c2c1)C(=O)NC4=O>>O=C1NC(=O)c2c1ccc1[nH]c3ccc(O)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e7283af0700a4001ac72fdbb3ed5f745 | C=C(c1ccccc1)c1cc2cc(OC)ccc2[nH]1.O=C1C=CC(=O)N1>>COc1ccc2[nH]c3c(-c4ccccc4)cc4c(c3c2c1)C(=O)NC4=O | C1(=CC=CC=C1)C(=C)C=1NC2=CC=C(C=C2C1)OC.C1(C=CC(N1)=O)=O>>COC1=CC=2C=3C4=C(C=C(C3NC2C=C1)C1=CC=CC=C1)C(NC4=O)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]([C:9]([c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)=[CH2:16])[cH:19][c:20]2[cH:21]1.[CH:17]1=[CH:18][C:22](=[O:23])[NH:24][C:25]1=[O:26]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[nH:7][c:8]3[c:9](-[c:10]4[cH:11][cH:12][cH:13][cH:14][cH:15]4)[cH:16][c:17]4[c:18]([c:19]3[c:20]2[... | C=C(c1ccccc1)c1cc2cc(OC)ccc2[nH]1.O=C1C=CC(=O)N1 | COc1ccc2[nH]c3c(-c4ccccc4)cc4c(c3c2c1)C(=O)NC4=O | null | null | null | Miscellaneous | OtherReaction | 8fd53892c6f95a0a445846d9674be0e26fba6bf545b8b38fd5a439008db94b85 | 62104ffcb4d4ab6482284e0c7ae124bc1d1d4f4befe80d570c6848ac4dc98f52 | O=C1NC(=O)c2c1cc(-c1ccccc1)c1[nH]c3ccccc3c21 | [CH2;D1;+0:1]=[C;H0;D3;+0:2](-[c:3]1:[#7;a:4]:[c:5](:[c:6]):[c:7](:[c:8]):[cH;D2;+0:9]:1)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[O;D1;H0:15]=[C:16]1-[#7:17]-[C:18](=[O;D1;H0:19])-[CH;D2;+0:20]=[CH;D2;+0:21]-1>>[O;D1;H0:15]=[C:16]1-[#7:17]-[C:18](=[O;D1;H0:19])-[c;H0;D3;+0:20]2:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c;H0... | 73 | [{"value": 73.0, "product": "COC1=CC=2C=3C4=C(C=C(C3NC2C=C1)C1=CC=CC=C1)C(NC4=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Reaction of (818) prepared as described in example 418 with maleimide at 180° C. using the procedure described in example 69 gave the adduct (XCVIII; R=phenyl, R′═H) (819), which was used without further purification. The crude Diels-Alder adduct was aromatised with MnO2 using the procedure described in example 79 to g... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | c1ccc2[nH]ccc2c1.C1=CCNC1 | c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | c1ccccc1.c1ccc2c(c1)[nH]c1ccc3c(c12)CNC3 | null | null | null | null | C=C(c1ccccc1)c1cc2cc(OC)ccc2[nH]1.O=C1C=CC(=O)N1>>COc1ccc2[nH]c3c(-c4ccccc4)cc4c(c3c2c1)C(=O)NC4=O |
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