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-825b576ec3824178b44550c35afa2831 | CC(C)(C)OC(=O)N1CCC(CNc2c(N)cnc3cc(Br)ccc23)CC1.CCCC(OC)(OC)OC>>CCCc1nc2cnc3cc(Br)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1 | NC=1C=NC2=CC(=CC=C2C1NCC1CCN(CC1)C(=O)OC(C)(C)C)Br.C(CCC)(OC)(OC)OC>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC3CCN(CC3)C(=O)OC(C)(C)C)CCC | [NH2:5][c:6]1[cH:7][n:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]2[c:16]1[NH:17][CH2:18][CH:19]1[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]1.CO[C:4](OC)(OC)[CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][n:8][c:9]3[cH:10][c:11]([Br:12])[cH:1... | CC(C)(C)OC(=O)N1CCC(CNc2c(N)cnc3cc(Br)ccc23)CC1.CCCC(OC)(OC)OC | CCCc1nc2cnc3cc(Br)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 8d87c769e65778c9400c7f523e0409ecf0ffad86543cd9fdd6ef4b239323db96 | a60e703c3cf5c0d933aa031358d338c45d96ec82dec3fc2d9f5dce06b9dcc651 | c1ccc2c(c1)ncc1ncn(CC3CCNCC3)c12 | C-O-[C;H0;D4;+0:1](-O-C)(-O-C)-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C:4]-[C:5]-[n;H0;D3;+0:6]1:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[n;H0;D2;+0:13]:[c;H0;D3;+0:1]:1-[C:2]-[C:3] | 77.9 | [{"value": 77.9, "product": "BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC3CCN(CC3)C(=O)OC(C)(C)C)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The method described in Part A of Examples 142–144 was used to treat tert-butyl 4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]piperidine-1-carboxylate (15.0 g, 34.5 mmol) with trimethyl orthobutyrate (5.62 g, 37.9 mmol). After completion, the reaction mixture was concentrated under reduced pressure, and the residue was ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.C1CC[NH]CC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(CNc2c(N)cnc3cc(Br)ccc23)CC1.CCCC(OC)(OC)OC>>CCCc1nc2cnc3cc(Br)ccc3c2n1CC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ed6c6d0d8e3d4c479e339443c4683a34 | CC(C)(C)OC(=O)N1CCN(CCN)CC1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>CC(C)(C)OC(=O)N1CCN(CCNc2c([N+](=O)[O-])cnc3cc(Br)ccc23)CC1 | BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])Cl.NCCN1CCN(CC1)C(=O)OC(C)(C)C>>BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCN1CCN(CC1)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][NH2:14])[CH2:29][CH2:30]1.Cl[c:15]1[c:16]([N+:17](=[O:18])[O-:19])[cH:20][n:21][c:22]2[cH:23][c:24]([Br:25])[cH:26][cH:27][c:28]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][NH... | CC(C)(C)OC(=O)N1CCN(CCN)CC1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl | CC(C)(C)OC(=O)N1CCN(CCNc2c([N+](=O)[O-])cnc3cc(Br)ccc23)CC1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2c(NCCN3CCNCC3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:3]-[c:2]1:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 59.8 | [{"value": 59.8, "product": "BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCN1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 7-Bromo-4-chloro-3-nitroquinoline (33.0 g, 115 mmol) was treated with 4-(2-aminoethyl)-1-(tert-butoxycarbonyl)piperazine (26.4 mL, 115 mmol) according to the method described in Part E of Example 1. The reaction was stirred overnight. The crude product was triturated with diethyl ether and isolated by filtration to pro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | C1C[NH]CC[NH]1.c1ccc2ncccc2c1 | HCl | null | null | 8 | CC(C)(C)OC(=O)N1CCN(CCN)CC1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>CC(C)(C)OC(=O)N1CCN(CCNc2c([N+](=O)[O-])cnc3cc(Br)ccc23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fde1062fb7e5468ca3c9b1d8f714ccd0 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC[N+]1([O-])CCN(C(=O)OC(C)(C)C)CC1.ClP(Cl)Cl>>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCN1CCNCC1.Cl.Cl | NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC[N+]2(CCN(CC2)C(=O)OC(C)(C)C)[O-])COCC)Br.P(Cl)(Cl)Cl>>Cl.Cl.BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CCN3CCNCC3)COCC | CC(C)(C)OC(=O)[N:25]1[CH2:24][CH2:23][N+:22]([O-])([CH2:21][CH2:20][n:19]2[c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:6][c:7]3[c:8]([NH2:9])[n:10][c:11]4[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]4[c:18]32)[CH2:27][CH2:26]1.ClP([Cl:28])[Cl:29]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC[N+]1([O-])CCN(C(=O)OC(C)(C)C)CC1.ClP(Cl)Cl | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCN1CCNCC1.Cl.Cl | null | O | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | baebd3535e3c3ed48ea5d112df2046b97d58245c6fb078b0192e50e124437cab | f6a4ae6324f8dbd1ee43b452848ffb52b7dc085d08b53e9c735ec57db6466f6c | c1ccc2c(c1)ncc1ncn(CCN3CCNCC3)c12 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[N+;H0;D4:4](-[O-])(-[C:5]-[C:6])-[C:7]-[C:8]-1.Cl-P(-[Cl;H0;D1;+0:9])-[Cl;H0;D1;+0:10]>>[C:6]-[C:5]-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:8]-[C:7]-1.[ClH;D0;+0:9].[ClH;D0;+0:10] | 84.2 | [{"value": 84.2, "product": "Cl.Cl.BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CCN3CCNCC3)COCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 4 | CELSIUS | 45 | MINUTE | A solution of tert-butyl 4-[2-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]-4-oxidopiperazine-1-carboxylate (8.84 g, 16.1 mmol) in chloroform (400 mL) was cooled to 4° C. Phosphorous trichloride (9.82 mL, 113 mmol) was added dropwise, and the reaction was stirred for 45 minutes at 4° C. Water (o... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine.Tertiary amine | C1C[NH+]CC[NH]1 | C1C[NH]CCN1 | c1ccc2c(c1)ncc1[nH]cnc12.C1C[NH]CCN1 | HCl | O.C(Cl)(Cl)Cl | 4 | 0.75 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC[N+]1([O-])CCN(C(=O)OC(C)(C)C)CC1.ClP(Cl)Cl>O.C(Cl)(Cl)Cl>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCN1CCNCC1.Cl.Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1be1f82b79c64a0c962f9a12b8547cb9 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCN1CCNCC1.c1cncc(B2OCCCO2)c1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN1CCNCC1 | O.C([O-])([O-])=O.[Na+].[Na+].Cl.Cl.BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CCN3CCNCC3)COCC.B1(OCCCO1)C2=CN=CC=C2>>C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)C=2C=NC=CC2)N)N1)CCN1CCNCC1 | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:24]([CH2:25][CH2:26][N:27]4[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]4)[c:23]3[c:22]2[cH:21][cH:20]1.C1COB([c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)OC1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCN1CCNCC1.c1cncc(B2OCCCO2)c1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN1CCNCC1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | C(CC)O.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic esters | 2cd1cbe6f17c98cb5223a75d20dfc144a6eae8461c4fe8a7e9cc4bc7ecadb166 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1cncc(-c2ccc3c(c2)ncc2ncn(CCN4CCNCC4)c23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.C1-C-O-B(-[c;H0;D3;+0:13]2:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:2)-O-C-1>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13]3:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:3):[c:2]:[c:3]:2:[#7;a:4]:[c:5... | 78.9 | [{"value": 78.9, "product": "C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)C=2C=NC=CC2)N)N1)CCN1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Under a nitrogen atmosphere, triphenylphosphine (0.0409 g, 0.156 mmol), 2 M aqueous sodium carbonate (18.3 mL, 36.5 mmol) and a solution of palladium (II) acetate (0.0117 g, 0.52 mmol) in warm toluene were added to a solution of 7-bromo-2-ethoxymethyl-1-(2-piperazin-1-ylethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydroc... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2c(c1)ncc1[nH]cnc12.B1OCCCO1.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1.C1C[NH]CCN1 | HBr.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(CC)O.C1(=CC=CC=C1)C | null | null | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCN1CCNCC1.c1cncc(B2OCCCO2)c1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(CC)O.C1(=CC=CC=C1)C>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCN1CCNCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd064fe13c304d048f8985c83af1053f | CC(C)(O)CNc1c(N)cnc2cc(Br)ccc12.CCCC(OC)(OC)OC>>CCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)O | C(CCC)(OC)(OC)OC.Cl.N1=CC=CC=C1.NC=1C=NC2=CC(=CC=C2C1NCC(C)(O)C)Br>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)(O)C)CCC | [NH2:5][c:6]1[cH:7][n:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]2[c:16]1[NH:17][CH2:18][C:19]([CH3:20])([CH3:21])[OH:22].CO[C:4](OC)(OC)[CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][n:8][c:9]3[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]3[c:16]2[n:17]1[CH2:18][C:19]([CH3:20])([CH3:21])[OH:22] | CC(C)(O)CNc1c(N)cnc2cc(Br)ccc12.CCCC(OC)(OC)OC | CCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)O | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 8d87c769e65778c9400c7f523e0409ecf0ffad86543cd9fdd6ef4b239323db96 | a60e703c3cf5c0d933aa031358d338c45d96ec82dec3fc2d9f5dce06b9dcc651 | c1ccc2c(c1)ncc1nc[nH]c12 | C-O-[C;H0;D4;+0:1](-O-C)(-O-C)-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C:4]-[C:5]-[n;H0;D3;+0:6]1:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[n;H0;D2;+0:13]:[c;H0;D3;+0:1]:1-[C:2]-[C:3] | 76.7 | [{"value": 76.7, "product": "BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)(O)C)CCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Trimethyl orthobutyrate (11.61 mL, 72.6 mmol) and catalytic pyridine hydrochloride were added to a solution of 1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol (22.51 g, 72.6 mmol) in anhydrous toluene (120 mL), and the reaction was heated at reflux for two hours. The solvent was removed under reduced pressure... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | HO- | C1(=CC=CC=C1)C | null | null | CC(C)(O)CNc1c(N)cnc2cc(Br)ccc12.CCCC(OC)(OC)OC>C1(=CC=CC=C1)C>CCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)(C)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a0aab8bc0b124b31a57accf5057cc740 | CC(C)Cn1cnc2c(N)nc3ccccc3c21.O=C1CCC(=O)N1Br>>CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21 | CC(CN1C=NC=2C(=NC=3C=CC=CC3C21)N)C.BrN1C(CCC1=O)=O>>BrC1=CC=2C3=C(C(=NC2C=C1)N)N=CN3CC(C)C | [CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][cH:15][cH:17][c:18]3[c:19]12.O=C1CCC(=O)N1[Br:16]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][c:15]([Br:16])[cH:17][c:18]3[c:19]12 | CC(C)Cn1cnc2c(N)nc3ccccc3c21.O=C1CCC(=O)N1Br | CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21 | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Bromination | 5d9faf536b16c566a8d6a04595b0f955faec3d2832e3b158ede2e30e6cf6e4a4 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1ccc2c(c1)ncc1nc[nH]c12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[c:3]1:[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]:1:[c:9]:[#7;a:10]>>[#7;a:2]:[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6](-[Br;H0;D1;+0:1]):[c:7]:[c:8]:1:[c:9]:[#7;a:10] | 22.6 | [{"value": 22.6, "product": "BrC1=CC=2C3=C(C(=NC2C=C1)N)N=CN3CC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (30.0 g, 125 mmol) in chloroform (620 mL) was heated to 50° C., and N-bromosuccinimide (28.8 g, 162 mmol) was added in five portions over a period of five minutes. The resulting dark red solution was heated at reflux for 45 minutes, allowed to cool to a... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2ccccc2c2[nH]cnc12.C1CCNC1 | c1ccc2ncc3nc[nH]c3c2c1 | c1ccc2ncc3nc[nH]c3c2c1 | HO- | C(Cl)(Cl)Cl | null | 1 | CC(C)Cn1cnc2c(N)nc3ccccc3c21.O=C1CCC(=O)N1Br>C(Cl)(Cl)Cl>CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-06dcb0dc9288479ba77db93b0ebf51a7 | C=Cc1ccncc1.CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21>>CC(C)Cn1cnc2c(N)nc3ccc(C=Cc4ccncc4)cc3c21 | BrC1=CC=2C3=C(C(=NC2C=C1)N)N=CN3CC(C)C.C(=C)C1=CC=NC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)N(CC)CC>>CC(CN1C=NC=2C(=NC=3C=CC(=CC3C21)C=CC2=CC=NC=C2)N)C | [CH2:16]=[CH:17][c:18]1[cH:19][cH:20][n:21][cH:22][cH:23]1.Br[c:15]1[cH:14][cH:13][c:12]2[n:11][c:9]([NH2:10])[c:8]3[n:7][cH:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:26]3[c:25]2[cH:24]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][c:15]([CH:16]=[CH:17][c:18]4[cH:19][cH... | C=Cc1ccncc1.CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21 | CC(C)Cn1cnc2c(N)nc3ccc(C=Cc4ccncc4)cc3c21 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C(C)#N | C-C Coupling | Heck terminal vinyl | 4d5b3e3981a57b3aeb73174e1869a0103c791712a7b3c712b27e875529a5446f | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | C(=Cc1ccc2ncc3nc[nH]c3c2c1)c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[c:7]:1):[c:8]:[#7;a:9].[CH2;D1;+0:10]=[C:11]-[c:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[CH;D2;+0:10]=[C:11]-[c:12]):[c:7]:[c:6]:1:[c:8]:[#7;a:9] | 65.1 | [{"value": 65.1, "product": "CC(CN1C=NC=2C(=NC=3C=CC(=CC3C21)C=CC2=CC=NC=C2)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | Nitrogen was bubbled through a solution of 8-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]-quinolin-4-amine (3.0 g, 9.4 mmol), 4-vinylpyridine (2.0 mL, 19 mmol), triphenylphosphine (246 mg, 0.94 mmol), and triethylamine (2.7 mL, 19 mmol) in acetonitrile (50 mL) for 15 minutes. Palladium (II) acetate (105 mg, 0.47 mmol) wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1ccc2ncc3[nH]cnc3c2c1 | c1ccc2ncc3nc[nH]c3c2c1 | c1ccc2ncc3nc[nH]c3c2c1.c1ccncc1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)#N | 100 | null | C=Cc1ccncc1.CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C(C)#N>CC(C)Cn1cnc2c(N)nc3ccc(C=Cc4ccncc4)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-599b5e90987942499a26d367a008765e | CC(C)Cn1cnc2c(N)nc3ccc(C=Cc4ccncc4)cc3c21>>CC(C)Cn1cnc2c(N)nc3ccc(CCc4ccncc4)cc3c21 | CC(CN1C=NC=2C(=NC=3C=CC(=CC3C21)C=CC2=CC=NC=C2)N)C>>CC(CN1C=NC=2C(=NC=3C=CC(=CC3C21)CCC2=CC=NC=C2)N)C | [CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][c:15]([CH:16]=[CH:17][c:18]4[cH:19][cH:20][n:21][cH:22][cH:23]4)[cH:24][c:25]3[c:26]12>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][c:15]([CH2:16][CH2:17][c:18]4[cH:19][cH:20... | CC(C)Cn1cnc2c(N)nc3ccc(C=Cc4ccncc4)cc3c21 | CC(C)Cn1cnc2c(N)nc3ccc(CCc4ccncc4)cc3c21 | null | [Pd] | CO | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1cc(CCc2ccc3ncc4nc[nH]c4c3c2)ccn1 | [c:1]:[c:2](-[CH;D2;+0:3]=[CH;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1):[c:11]>>[c:1]:[c:2](-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1):[c:11] | 18 | [{"value": 18.0, "product": "CC(CN1C=NC=2C(=NC=3C=CC(=CC3C21)CCC2=CC=NC=C2)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | DAY | 1-(2-Methylpropyl)-8-(2-pyridin-4-ylvinyl)-1H-imidazo[4,5-c]-quinolin-4-amine (2.1 g, 6.1 mmol) was treated according to the method described in Example 123; the reaction was allowed to run for seven days. An analysis by proton nuclear magnetic resonance spectroscopy indicated the presence of starting material in the p... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2ncc3nc[nH]c3c2c1.c1ccncc1 | null | [Pd].CO | null | 168 | CC(C)Cn1cnc2c(N)nc3ccc(C=Cc4ccncc4)cc3c21>[Pd].CO>CC(C)Cn1cnc2c(N)nc3ccc(CCc4ccncc4)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8018ff66f1b14643aeb0cf875f55bc8b | C=CCCc1ccccc1.CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21>>CC(C)Cn1cnc2c(N)nc3ccc(C=CCCc4ccccc4)cc3c21 | BrC1=CC=2C3=C(C(=NC2C=C1)N)N=CN3CC(C)C.C1(=CC=CC=C1)CCC=C>>CC(CN1C=NC=2C(=NC=3C=CC(=CC3C21)C=CCCC2=CC=CC=C2)N)C | [CH2:16]=[CH:17][CH2:18][CH2:19][c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1.Br[c:15]1[cH:14][cH:13][c:12]2[n:11][c:9]([NH2:10])[c:8]3[n:7][cH:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:28]3[c:27]2[cH:26]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][c:15]([CH:16]=[CH:17]... | C=CCCc1ccccc1.CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21 | CC(C)Cn1cnc2c(N)nc3ccc(C=CCCc4ccccc4)cc3c21 | null | null | null | C-C Coupling | OtherReaction | 5c2a497c119c97c63096a3705db7c6fc998936207eb8d13d39dcfae27041b2b5 | df8442c9f2045421fb18548edb9c6acaeb9710f63e741d9f72e0000ca35c948a | C(=Cc1ccc2ncc3nc[nH]c3c2c1)CCc1ccccc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[c:7]:1):[c:8]:[#7;a:9].[C:10]-[C:11]=[CH2;D1;+0:12]>>[#7;a:5]:[c:4]1:[c:3]:[c:2]:[c;H0;D3;+0:1](-[CH;D2;+0:12]=[C:11]-[C:10]):[c:7]:[c:6]:1:[c:8]:[#7;a:9] | 51.7 | [{"value": 51.7, "product": "CC(CN1C=NC=2C(=NC=3C=CC(=CC3C21)C=CCCC2=CC=CC=C2)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 8-Bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (3.0 g, 9.4 mmol) was treated with 4-phenyl butene (4.2 mL, 28.2 mmol) according to the method described in Part B of Example 425. The reaction was heated overnight. Following chromatographic purification (eluting with 95:5 chloroform:methanol), 1.8 g of 1-(2... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Allyl | null | c1ccc2ncc3[nH]cnc3c2c1 | c1ccc2ncc3nc[nH]c3c2c1 | c1ccc2ncc3nc[nH]c3c2c1.c1ccccc1 | HBr | null | null | null | C=CCCc1ccccc1.CC(C)Cn1cnc2c(N)nc3ccc(Br)cc3c21>>CC(C)Cn1cnc2c(N)nc3ccc(C=CCCc4ccccc4)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aae0dad34e834b03a63c256ec63dadca | CC(C)CNc1c([N+](=O)[O-])cnc2cc(Br)ccc12>>CC(C)CNc1c(N)cnc2cc(Br)ccc12 | BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCC(C)C>>BrC1=CC=C2C(=C(C=NC2=C1)N)NCC(C)C | O=[N+:8]([O-])[c:7]1[c:6]([NH:5][CH2:4][CH:2]([CH3:1])[CH3:3])[c:17]2[c:11]([n:10][cH:9]1)[cH:12][c:13]([Br:14])[cH:15][cH:16]2>>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][c:6]1[c:7]([NH2:8])[cH:9][n:10][c:11]2[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]12 | CC(C)CNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 | CC(C)CNc1c(N)cnc2cc(Br)ccc12 | null | [Pt] | C(C)(C)O.C(C)#N | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ncccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | null | [] | null | null | 1 | HOUR | A solution of (7-bromo-3-nitroquinolin-4-yl)-(2-methylpropyl)amine (30.9 g, 105 mmol) in acetonitrile (1.8 L) and isopropanol (200 mL) was added to a Parr vessel. A mixture of 5% platinum on carbon (3.0 g) and acetonitrile:isopropanol (20 mL) was added, and the vessel was purged with nitrogen. The vessel was placed und... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1 | Other | [Pt].C(C)(C)O.C(C)#N | null | 1 | CC(C)CNc1c([N+](=O)[O-])cnc2cc(Br)ccc12>[Pt].C(C)(C)O.C(C)#N>CC(C)CNc1c(N)cnc2cc(Br)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-755d4f9ae9fc48b3bfbb003cb502e6b9 | CC(C)Cn1cnc2cnc3cc(Br)ccc3c21.[NH4+]>>CC(C)Cn1cnc2c(N)nc3cc(Br)ccc3c21 | BrC=1C=CC=2C3=C(C=NC2C1)N=CN3CC(C)C.ClC=1C=C(C(=O)OO)C=CC1.[OH-].[NH4+].C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>BrC=1C=CC=2C3=C(C(=NC2C1)N)N=CN3CC(C)C | [CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[cH:9][n:11][c:12]3[cH:13][c:14]([Br:15])[cH:16][cH:17][c:18]3[c:19]12.[NH4+:10]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][c:14]([Br:15])[cH:16][cH:17][c:18]3[c:19]12 | CC(C)Cn1cnc2cnc3cc(Br)ccc3c21.[NH4+] | CC(C)Cn1cnc2c(N)nc3cc(Br)ccc3c21 | null | null | C(C)#N | Functional Group Addition | OtherReaction | 1b385f4f663d9a767870cf79c8a1cc13167a133dcf33a738d88383ea6a59da05 | d69ce1fde4173969963123914389bef807fad83b73b8a587195a7122d5cdf1d2 | c1ccc2c(c1)ncc1nc[nH]c12 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[cH;D2;+0:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:1:2.[NH4+;D0:11]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:10]:1:[c:9]:[c:8]:[#7;a:7]:[c;H0;D3;+0:6]:2-[NH2;D1;+0:11] | null | [] | null | null | null | null | The method described in Part J of Example 365 was used to oxidize and aminate 7-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (18.7 g, 58.4 mmol). 3-Chloroperoxybenzoic acid (22.1 g of 50% pure material, 129 mmol) was added in five portions during the oxidation step, and the amination with ammonium hydroxide (146... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccc2c(c1)ncc1nc[nH]c12 | c1ccc2c(c1)ncc1nc[nH]c12 | c1ccc2c(c1)ncc1nc[nH]c12 | null | C(C)#N | null | null | CC(C)Cn1cnc2cnc3cc(Br)ccc3c21.[NH4+]>C(C)#N>CC(C)Cn1cnc2c(N)nc3cc(Br)ccc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f357290ac0064a0c9824d3f113be41d2 | CC(C)Cn1cnc2c(N)nc3cc(C=Cc4ccccc4)ccc3c21>>CC(C)Cn1cnc2c(N)nc3cc(CCc4ccccc4)ccc3c21 | CC(CN1C=NC=2C(=NC=3C=C(C=CC3C21)C=CC2=CC=CC=C2)N)C>>CC(CN1C=NC=2C(=NC=3C=C(C=CC3C21)CCC2=CC=CC=C2)N)C | [CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][c:14]([CH:15]=[CH:16][c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[cH:23][cH:24][c:25]3[c:26]12>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][c:14]([CH2:15][CH2:16][c:17]4[cH:18][cH:19][cH:2... | CC(C)Cn1cnc2c(N)nc3cc(C=Cc4ccccc4)ccc3c21 | CC(C)Cn1cnc2c(N)nc3cc(CCc4ccccc4)ccc3c21 | null | null | CO | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(CCc2ccc3c(c2)ncc2nc[nH]c23)cc1 | [#7;a:1]:[c:2]:[c:3]:[c:4](-[CH;D2;+0:5]=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:10]>>[#7;a:1]:[c:2]:[c:3]:[c:4](-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:10] | null | [] | null | null | null | null | A modification of the method described in Example 123 was used to reduce 1-(2-methylpropyl)-7-styryl-1H-imidazo[4,5-c]quinolin-4-amine (1.2 g, 3.5 mmol). The reaction was carried out in methanol (100 mL) for seven days. The crude product was purified by flash column chromatography on silica gel (eluting with 90:10 chlo... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)ncc1nc[nH]c12.c1ccccc1 | null | CO | null | null | CC(C)Cn1cnc2c(N)nc3cc(C=Cc4ccccc4)ccc3c21>CO>CC(C)Cn1cnc2c(N)nc3cc(CCc4ccccc4)ccc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1497b3ef15dc4b0aace9e821cdb10a10 | CC1(C)OC(=O)CC(=O)O1.CCOC(OCC)OCC.Nc1ccc(Cc2ccccc2)cc1.Nc1cccc(Cc2ccccc2)c1>>CC1(C)OC(=O)C(=CNc2ccc(Cc3ccccc3)cc2)C(=O)O1.CC1(C)OC(=O)C(=CNc2cccc(Cc3ccccc3)c2)C(=O)O1 | C(C1=CC=CC=C1)C=1C=C(N)C=CC1.C(OCC)(OCC)OCC.C(C1=CC=CC=C1)C1=CC=C(N)C=C1.CC1(OC(=O)CC(=O)O1)C>>C(C1=CC=CC=C1)C=1C=C(C=CC1)NC=C1C(OC(OC1=O)(C)C)=O.C(C1=CC=CC=C1)C1=CC=C(C=C1)NC=C1C(OC(OC1=O)(C)C)=O | [CH3:1][C:2]1([CH3:3])[O:4][C:5](=[O:6])[CH2:7][C:48](=[O:49])[O:25]1.[CH2:8]([CH3:23])[O:24][CH:33]([O:29][CH2:27][CH3:28])[O:31][CH2:30][CH3:32].[NH2:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][cH:22]1.[NH2:34][c:35]1[cH:36][cH:37][cH:38][c:39]([CH2:40][c:41]2[cH:42][cH:4... | CC1(C)OC(=O)CC(=O)O1.CCOC(OCC)OCC.Nc1ccc(Cc2ccccc2)cc1.Nc1cccc(Cc2ccccc2)c1 | CC1(C)OC(=O)C(=CNc2ccc(Cc3ccccc3)cc2)C(=O)O1.CC1(C)OC(=O)C(=CNc2cccc(Cc3ccccc3)c2)C(=O)O1 | null | null | CO | Functional Group Addition | OtherReaction | c5e983f3b9e5026f979cb69feab0c38fb2eb5aa05407ae38d616c63063338bac | 5c401633cc6fe8ba0d915d7e01cfff26b7da6dac9d076e92ffd0965d9724e26b | O=C1OCOC(=O)C1=CNc1ccc(Cc2ccccc2)cc1.O=C1OCOC(=O)C1=CNc1cccc(Cc2ccccc2)c1 | [C;D1;H3:1]-[CH2;D2;+0:2]-[O;H0;D2;+0:3]-[CH;D3;+0:4](-[O;H0;D2;+0:5]-[CH2;D2;+0:6]-[CH3;D1;+0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:9]-[CH3;D1;+0:10].[C;D1;H3:11]-[C:12]1(-[C;D1;H3:13])-[#8:14]-[C:15](=[O;D1;H0:16])-[CH2;D2;+0:17]-[C;H0;D3;+0:18](=[O;D1;H0:19])-[O;H0;D2;+0:20]-1.[NH2;D1;+0:21]-[c:22](:[c:23]):[c:24].[NH2;D1;+... | null | [] | null | null | null | null | Triethyl orthoformate (10.0 mL, 60.1 mmol), Meldrum's acid (8.2 g, 57 mmol), and either 3-benzyl aniline or 4-benzyl aniline (10.0 g, 54.6 mmol) as indicated in the table below in methanol (303 mL) were combined and treated according to the method described in Part A of Example 1 to provide 5-[(3-benzylphenylamino)meth... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Ether.Ether.Primary amine.Primary amine | Enamine.Enamine.Ester.Ester.Ester.Ester | C1COCOC1 | C1COCOC1.C1COCOC1 | C1COCOC1.c1ccccc1.c1ccccc1.C1COCOC1.c1ccccc1.c1ccccc1 | Other | CO | null | null | CC1(C)OC(=O)CC(=O)O1.CCOC(OCC)OCC.Nc1ccc(Cc2ccccc2)cc1.Nc1cccc(Cc2ccccc2)c1>CO>CC1(C)OC(=O)C(=CNc2ccc(Cc3ccccc3)cc2)C(=O)O1.CC1(C)OC(=O)C(=CNc2cccc(Cc3ccccc3)c2)C(=O)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-784d2dd1f34043149cecc0d483a46e48 | O=[N+]([O-])O.Oc1ccnc2cc(Cc3ccccc3)ccc12.Oc1ccnc2ccc(Cc3ccccc3)cc12>>O=[N+]([O-])c1cnc2cc(Cc3ccccc3)ccc2c1O.O=[N+]([O-])c1cnc2ccc(Cc3ccccc3)cc2c1O | C(C1=CC=CC=C1)C1=CC=C2C(=CC=NC2=C1)O.C(C1=CC=CC=C1)C=1C=C2C(=CC=NC2=CC1)O.[N+](=O)(O)[O-]>>C(C1=CC=CC=C1)C1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])O.C(C1=CC=CC=C1)C=1C=C2C(=C(C=NC2=CC1)[N+](=O)[O-])O | [O:1]=[N+:23]([OH:3])[O-:24].[cH:4]1[cH:5][n:6][c:7]2[cH:8][c:9]([CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18][c:19]2[c:20]1[OH:21].[n:2]1[cH:26][cH:25][c:41]([OH:42])[c:40]2[c:28]1[cH:29][cH:30][c:31]([CH2:32][c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1)[cH:39]2>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:... | O=[N+]([O-])O.Oc1ccnc2cc(Cc3ccccc3)ccc12.Oc1ccnc2ccc(Cc3ccccc3)cc12 | O=[N+]([O-])c1cnc2cc(Cc3ccccc3)ccc2c1O.O=[N+]([O-])c1cnc2ccc(Cc3ccccc3)cc2c1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | e4cc7b0e705a045ffe673b7312da26eefcc4ceb4b30b7b809794b816d906d64d | 6674cfa36c1a7a9bb1f0df0b4aa5b94d1b581f7b4be96876f34ffacfa3ea15db | c1ccc(Cc2ccc3cccnc3c2)cc1.c1ccc(Cc2ccc3ncccc3c2)cc1 | [O;-;D1;H0:1]-[N+;H0;D3:2](=[O;H0;D1;+0:3])-[OH;D1;+0:4].[O;D1;H1:5]-[c:6]1:[cH;D2;+0:7]:[cH;D2;+0:8]:[n;H0;D2;+0:9]:[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:1:[c:14].[O;D1;H1:15]-[c:16]1:[c:17]:[c:18]:[#7;a:19]:[c:20]:[cH;D2;+0:21]:1>>[O-;H0;D1:4]-[N+;H0;D3:9](=[O;H0;D1;+0:3])-[c;H0;D3;+0:21]1:[c:20]:[#7;a:19]:[c:18]:[c... | null | [] | null | null | null | null | The method described in Part D of Example 10 was used to treat 7-benzylquinolin-4-ol or 6-benzylquinolin-4-ol with nitric acid to provide 7-benzyl-3-nitroquinolin-4-ol or 6-benzyl-3-nitroquinolin-4-ol, respectively, as solids.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group.Nitro group | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1.c1ccc2ncccc2c1.c1ccccc1 | null | null | null | null | O=[N+]([O-])O.Oc1ccnc2cc(Cc3ccccc3)ccc12.Oc1ccnc2ccc(Cc3ccccc3)cc12>>O=[N+]([O-])c1cnc2cc(Cc3ccccc3)ccc2c1O.O=[N+]([O-])c1cnc2ccc(Cc3ccccc3)cc2c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-89dff75aa83d4c2c8be904ac12f724d0 | O=P(Cl)(Cl)Cl.O=[N+]([O-])c1cnc2cc(Cc3ccccc3)ccc2c1O.O=[N+]([O-])c1cnc2ccc(Cc3ccccc3)cc2c1O>>O=[N+]([O-])c1cnc2cc(Cc3ccccc3)ccc2c1Cl.O=[N+]([O-])c1cnc2ccc(Cc3ccccc3)cc2c1Cl | C(C1=CC=CC=C1)C1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])O.C(C1=CC=CC=C1)C=1C=C2C(=C(C=NC2=CC1)[N+](=O)[O-])O.P(=O)(Cl)(Cl)Cl>>C(C1=CC=CC=C1)C1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])Cl.C(C1=CC=CC=C1)C=1C=C2C(=C(C=NC2=CC1)[N+](=O)[O-])Cl | O=P(Cl)([Cl:21])[Cl:42].O[c:20]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[cH:8][c:9]([CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18][c:19]21.O[c:41]1[c:25]([N+:23](=[O:22])[O-:24])[cH:26][n:27][c:28]2[cH:29][cH:30][c:31]([CH2:32][c:33]3[cH:34][cH:35][cH:36][cH:37][cH:38]3)[cH:39][c:40]21>>[O:1]=[N... | O=P(Cl)(Cl)Cl.O=[N+]([O-])c1cnc2cc(Cc3ccccc3)ccc2c1O.O=[N+]([O-])c1cnc2ccc(Cc3ccccc3)cc2c1O | O=[N+]([O-])c1cnc2cc(Cc3ccccc3)ccc2c1Cl.O=[N+]([O-])c1cnc2ccc(Cc3ccccc3)cc2c1Cl | null | null | null | Functional Group Addition | OtherReaction | 62803afad24e75ce74a549b9c7ab0a60972fe8d8e6a394f7f72b0523bceb62a4 | d74bc1b012061488363cc8b67469d047228fe70d9f227566212bf2539e8291df | c1ccc(Cc2ccc3cccnc3c2)cc1.c1ccc(Cc2ccc3ncccc3c2)cc1 | Cl-P(=O)(-[Cl;H0;D1;+0:1])-[Cl;H0;D1;+0:2].O-[c;H0;D3;+0:3]1:[c:4](-[#7;+:5]):[c:6]:[#7;a:7]:[c:8](:[c:9]):[c:10]:1:[c:11].O-[c;H0;D3;+0:12]1:[c:13](:[c:14]):[c:15](:[c:16]):[#7;a:17]:[c:18]:[c:19]:1-[#7;+:20]>>[#7;+:20]-[c:19]1:[c:18]:[#7;a:17]:[c:15](:[c:16]):[c:13](:[c:14]):[c;H0;D3;+0:12]:1-[Cl;H0;D1;+0:1].[#7;+:5]... | null | [] | null | null | null | null | The method described in Part E of Example 10 was used to treat 7-benzyl-3-nitroquinolin-4-ol or 6-benzyl-3-nitroquinolin-4-ol with phosphorous oxychloride to provide 7-benzyl-4-chloro-3-nitroquinoline as a light yellow powder or 6-benzyl-4-chloro-3-nitroquinoline as a tan powder, respectively.
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol | Aromatic halide.Aromatic halide | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1.c1ccc2ncccc2c1.c1ccccc1 | HCl | null | null | null | O=P(Cl)(Cl)Cl.O=[N+]([O-])c1cnc2cc(Cc3ccccc3)ccc2c1O.O=[N+]([O-])c1cnc2ccc(Cc3ccccc3)cc2c1O>>O=[N+]([O-])c1cnc2cc(Cc3ccccc3)ccc2c1Cl.O=[N+]([O-])c1cnc2ccc(Cc3ccccc3)cc2c1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a26247a753df407cb8aa5733bcc350c4 | CC(C)(O)CN.CCN(CC)CC.O=[N+]([O-])c1cnc2cc(Cc3ccccc3)ccc2c1Cl.O=[N+]([O-])c1cnc2ccc(Cc3ccccc3)cc2c1Cl>>CC(C)(O)CNc1c([N+](=O)[O-])cnc2cc(Cc3ccccc3)ccc12.CC(C)(O)CNc1c([N+](=O)[O-])cnc2ccc(Cc3ccccc3)cc12 | NCC(C)(O)C.C(C1=CC=CC=C1)C1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])Cl.C(C1=CC=CC=C1)C=1C=C2C(=C(C=NC2=CC1)[N+](=O)[O-])Cl.C(C)N(CC)CC>>C(C1=CC=CC=C1)C1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCC(C)(O)C.C(C1=CC=CC=C1)C=1C=C2C(=C(C=NC2=CC1)[N+](=O)[O-])NCC(C)(O)C | [CH3:27][C:28]([CH3:29])([OH:30])[CH2:31][NH2:32].C[CH2:5][N:6](C[CH3:3])[CH2:2][CH3:1].Cl[c:7]1[c:8]([N+:9](=[O:10])[O-:11])[cH:12][n:13][c:14]2[cH:15][c:16]([CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[cH:24][cH:25][c:26]12.Cl[c:33]1[c:34]([N+:35](=[O:4])[O-:36])[cH:38][n:39][c:40]2[cH:41][cH:42][c:43]([CH2:4... | CC(C)(O)CN.CCN(CC)CC.O=[N+]([O-])c1cnc2cc(Cc3ccccc3)ccc2c1Cl.O=[N+]([O-])c1cnc2ccc(Cc3ccccc3)cc2c1Cl | CC(C)(O)CNc1c([N+](=O)[O-])cnc2cc(Cc3ccccc3)ccc12.CC(C)(O)CNc1c([N+](=O)[O-])cnc2ccc(Cc3ccccc3)cc12 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | 8070e49a703ee32ad1c4b70cc94cc74c320661b4caef4617a6bf3fecf414c14f | 545f73d1df2c6f4b6586383103a73876f5ba179ddc71535c47c7b1c16ee04be1 | c1ccc(Cc2ccc3cccnc3c2)cc1.c1ccc(Cc2ccc3ncccc3c2)cc1 | C-[CH2;D2;+0:1]-[N;H0;D3;+0:2](-C-[CH3;D1;+0:3])-[CH2;D2;+0:4]-[C;D1;H3:5].Cl-[c;H0;D3;+0:6]1:[c:7](-[N+;H0;D3:8](-[O-;H0;D1:9])=[O;H0;D1;+0:10]):[c:11]:[#7;a:12]:[c:13](:[c:14]):[c:15]:1:[c:16].Cl-[c;H0;D3;+0:17]1:[c:18](:[c:19]):[c:20](:[c:21]):[#7;a:22]:[c:23]:[c:24]:1-[#7;+:25].[C:26]-[C:27]-[NH2;D1;+0:28]>>[#7;+:2... | null | [] | null | null | 8 | HOUR | Under a nitrogen atmosphere, 1-amino-2-methylpropan-2-ol (1.2 equivalents) was added to a 0.2 M solution of 7-benzyl-4-chloro-3-nitroquinoline or 6-benzyl-4-chloro-3-nitroquinoline (1 equivalent) and triethylamine (3 equivalents) in dichloromethane, and the reaction was stirred overnight at ambient temperature. The vol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Nitro group.Primary amine.Tertiary amine | Nitro group.Tertiary alcohol.Secondary amine.Secondary amine | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccccc1.c1ccc2ncccc2c1.c1ccccc1 | HCl | ClCCl | null | 8 | CC(C)(O)CN.CCN(CC)CC.O=[N+]([O-])c1cnc2cc(Cc3ccccc3)ccc2c1Cl.O=[N+]([O-])c1cnc2ccc(Cc3ccccc3)cc2c1Cl>ClCCl>CC(C)(O)CNc1c([N+](=O)[O-])cnc2cc(Cc3ccccc3)ccc12.CC(C)(O)CNc1c([N+](=O)[O-])cnc2ccc(Cc3ccccc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8dca345f64d74c3baa164565dcda69f8 | CC(C)(O)CNc1c([N+](=O)[O-])cnc2cc(Cc3ccccc3)ccc12.CC(C)(O)CNc1c([N+](=O)[O-])cnc2ccc(Cc3ccccc3)cc12>>CC(C)(O)CNc1c(N)cnc2cc(Cc3ccccc3)ccc12.CC(C)(O)CNc1c(N)cnc2ccc(Cc3ccccc3)cc12 | C(C1=CC=CC=C1)C1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCC(C)(O)C.C(C1=CC=CC=C1)C=1C=C2C(=C(C=NC2=CC1)[N+](=O)[O-])NCC(C)(O)C>>NC=1C=NC2=CC(=CC=C2C1NCC(C)(O)C)CC1=CC=CC=C1.NC=1C=NC2=CC=C(C=C2C1NCC(C)(O)C)CC1=CC=CC=C1 | O=[N+:9]([O-])[c:8]1[c:7]([NH:6][CH2:5][C:2]([CH3:1])([CH3:3])[OH:4])[c:24]2[c:12]([n:11][cH:10]1)[cH:13][c:14]([CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)[cH:22][cH:23]2.O=[N+:33]([O-])[c:32]1[c:31]([NH:30][CH2:29][C:26]([CH3:25])([CH3:27])[OH:28])[c:48]2[c:36]([n:35][cH:34]1)[cH:37][cH:38][c:39]([CH2:40][c:4... | CC(C)(O)CNc1c([N+](=O)[O-])cnc2cc(Cc3ccccc3)ccc12.CC(C)(O)CNc1c([N+](=O)[O-])cnc2ccc(Cc3ccccc3)cc12 | CC(C)(O)CNc1c(N)cnc2cc(Cc3ccccc3)ccc12.CC(C)(O)CNc1c(N)cnc2ccc(Cc3ccccc3)cc12 | null | null | null | Functional Group Interconversion | OtherReaction | f469aaae1e88945b257afa41cebe21597b9a3f326d9f2ab1d5670c64dd831541 | 86e032c8ebc9cbcd13a880d0d66c541ff63611af16d12657aad958d17abf4587 | c1ccc(Cc2ccc3cccnc3c2)cc1.c1ccc(Cc2ccc3ncccc3c2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].O=[N+;H0;D3:7](-[O-])-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]:[#7;a:11]:[c:12] | null | [] | null | null | 2 | DAY | A modification of the method described in Part A of Examples 427–429 was used to reduce 1-(7-benzyl-3-nitroquinolin-4-ylamino)-2-methylpropan-2-ol or 1-(6-benzyl-3-nitroquinolin-4-ylamino)-2-methylpropan-2-ol. The reaction was shaken for one or two days to provide 1-(3-amino-7-benzylquinolin-4-ylamino)-2-methylpropan-2... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group | Primary amine.Primary amine | null | null | c1ccc2ncccc2c1.c1ccccc1.c1ccc2ncccc2c1.c1ccccc1 | Other | null | null | 48 | CC(C)(O)CNc1c([N+](=O)[O-])cnc2cc(Cc3ccccc3)ccc12.CC(C)(O)CNc1c([N+](=O)[O-])cnc2ccc(Cc3ccccc3)cc12>>CC(C)(O)CNc1c(N)cnc2cc(Cc3ccccc3)ccc12.CC(C)(O)CNc1c(N)cnc2ccc(Cc3ccccc3)cc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7c4ba5b0737a4f89b2ca5ce53f1a44b3 | CC(C)(O)CNc1c(N)cnc2cc(Cc3ccccc3)ccc12.CC(C)(O)CNc1c(N)cnc2ccc(Cc3ccccc3)cc12>>CC(C)(O)Cn1cnc2cnc3cc(Cc4ccccc4)ccc3c21.CC(C)(O)Cn1cnc2cnc3ccc(Cc4ccccc4)cc3c21 | NC=1C=NC2=CC(=CC=C2C1NCC(C)(O)C)CC1=CC=CC=C1.NC=1C=NC2=CC=C(C=C2C1NCC(C)(O)C)CC1=CC=CC=C1.C(OCC)(OCC)OCC>>C(C1=CC=CC=C1)C=1C=CC=2C3=C(C=NC2C1)N=CN3CC(C)(O)C.C(C1=CC=CC=C1)C1=CC=2C3=C(C=NC2C=C1)N=CN3CC(C)(O)C | [CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][NH:6][c:25]1[c:9]([NH2:8])[cH:10][n:11][c:12]2[cH:13][c:14]([CH2:15][c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[cH:22][cH:23][c:24]21.[CH3:26][C:27]([CH3:28])([OH:29])[CH2:30][NH:31][c:50]1[c:34]([NH2:33])[cH:35][n:36][c:37]2[cH:38][cH:39][c:40]([CH2:41][c:42]3[cH:43][cH:44][cH:45]... | CC(C)(O)CNc1c(N)cnc2cc(Cc3ccccc3)ccc12.CC(C)(O)CNc1c(N)cnc2ccc(Cc3ccccc3)cc12 | CC(C)(O)Cn1cnc2cnc3cc(Cc4ccccc4)ccc3c21.CC(C)(O)Cn1cnc2cnc3ccc(Cc4ccccc4)cc3c21 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | b6eba0d3ddf07d65a738d182c49e05e581b7c331dc24811a5939a71fcbc7ae87 | 23443a0287b53d223fe3b7fe1486262eb4d997ce605d04f578cd81fe2405710e | c1ccc(Cc2ccc3c(c2)ncc2nc[nH]c23)cc1.c1ccc(Cc2ccc3ncc4nc[nH]c4c3c2)cc1 | [C:1]-[C:2]-[NH;D2;+0:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1-[NH2;D1;+0:10].[C:11]-[C:12]-[NH;D2;+0:13]-[c:14]1:[c:15]:[c:16]:[#7;a:17]:[c:18]:[c:19]:1-[NH2;D1;+0:20]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[c:21]:[n;H0;D2;+0:10]:[c:9]2:[c:8]:[#7;a:7]:[c:6]:[c:5]:[c:4]:2:1.[C:11]-[C:12]-[n;H0;D3;+0:13]1:[c:22]:[n;H0;D2;+0:2... | null | [] | null | null | 8 | HOUR | For Examples 431 and 434, a modification of the method described in Part B of Examples 427–429 was used to treat 1-(3-amino-7-benzylquinolin-4-ylamino)-2-methylpropan-2-ol or 1-(3-amino-6-benzylquinolin-4-ylamino)-2-methylpropan-2-ol with triethyl orthoformate, as indicated in the table below. The reaction was heated a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Secondary amine.Secondary amine | null | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1nc[nH]c12.c1ccc2ncc3nc[nH]c3c2c1 | c1ccc2c(c1)ncc1nc[nH]c12.c1ccccc1.c1ccc2ncc3nc[nH]c3c2c1.c1ccccc1 | Other | null | null | 8 | CC(C)(O)CNc1c(N)cnc2cc(Cc3ccccc3)ccc12.CC(C)(O)CNc1c(N)cnc2ccc(Cc3ccccc3)cc12>>CC(C)(O)Cn1cnc2cnc3cc(Cc4ccccc4)ccc3c21.CC(C)(O)Cn1cnc2cnc3ccc(Cc4ccccc4)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-87647dbc841a4245be527a11092613db | NCC1CCCCC1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCC1CCCCC1 | C1(CCCCC1)CN.BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])Cl>>BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCC1CCCCC1 | [NH2:15][CH2:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1.Cl[c:14]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]2[c:14]1[NH:15][CH2:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1 | NCC1CCCCC1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl | O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCC1CCCCC1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2c(NCC3CCCCC3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 62.8 | [{"value": 62.8, "product": "BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCC1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | Under a nitrogen atmosphere, cyclohexylmethylamine (40.9 mL, 315 mmol) was added dropwise to a solution of 7-bromo-4-chloro-3-nitroquinoline (30.0 g, 105 mmol) in dichloromethane (524 mL). The reaction was stirred for 18 hours at ambient temperature and then concentrated under reduced pressure. Water (200 mL) was added... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.C1CCCCC1 | HCl | ClCCl | null | 18 | NCC1CCCCC1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>ClCCl>O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCC1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f41eaa09f57b47d7a510a6dea1c16c23 | CCOCC(=O)Cl.Nc1cnc2cc(Br)ccc2c1NCC1CCCCC1>>CCOCc1nc2cnc3cc(Br)ccc3c2n1CC1CCCCC1 | BrC1=CC=C2C(=C(C=NC2=C1)N)NCC1CCCCC1.C(C)OCC(=O)Cl>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC3CCCCC3)COCC | O=[C:5](Cl)[CH2:4][O:3][CH2:2][CH3:1].[NH2:6][c:7]1[cH:8][n:9][c:10]2[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]2[c:17]1[NH:18][CH2:19][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH:20]1[... | CCOCC(=O)Cl.Nc1cnc2cc(Br)ccc2c1NCC1CCCCC1 | CCOCc1nc2cnc3cc(Br)ccc3c2n1CC1CCCCC1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 101a087a520f159c722ba3d78ed38f5c3c1cf154206e5edbeb1e6397c929560f | 56ef83dfadec35a1cf1db968b807e178cc4924ce15bf36d774883783cef0f450 | c1ccc2c(c1)ncc1ncn(CC3CCCCC3)c12 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[#8:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[#8:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:13]:[c:12]2:[c:11]:[#7;a:10]:[c:9]:[c:8]:[c:7]:2:[n;H0;D3;+0:6]:1-[C:5]-[C:4] | null | [] | 90 | CELSIUS | null | null | A modification of the method described in Part A of Example 9 was used to treat 7-bromo-N4-(cyclohexylmethyl)quinoline-3,4-diamine (7.3 g, 22 mmol) with ethoxyacetyl chloride (2.75 mL, 24.0 mmol). The reaction was heated overnight at 90° C. and then concentrated under reduced pressure to provide 7-bromo-1-cylcohexylmet... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.C1CCCCC1 | HCl | null | 90 | null | CCOCC(=O)Cl.Nc1cnc2cc(Br)ccc2c1NCC1CCCCC1>>CCOCc1nc2cnc3cc(Br)ccc3c2n1CC1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5c4046931f764f058fe2c1ac6ff47cc0 | CCOCc1nc2cnc3cc(Br)ccc3c2n1CC1CCCCC1.[NH4+]>>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCCCC1 | BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC3CCCCC3)COCC.ClC=1C=C(C(=O)OO)C=CC1.[OH-].[NH4+].C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC3CCCCC3)COCC | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]3[c:18]2[n:19]1[CH2:20][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1.[NH4+:9]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]3[c:18]2[n:19]1[CH2:2... | CCOCc1nc2cnc3cc(Br)ccc3c2n1CC1CCCCC1.[NH4+] | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCCCC1 | null | null | C(C)#N | Functional Group Addition | OtherReaction | dc63235befaaf41df35292b6862b726098d8e1b79a2cef881f35b7cf9ff16606 | d69ce1fde4173969963123914389bef807fad83b73b8a587195a7122d5cdf1d2 | c1ccc2c(c1)ncc1ncn(CC3CCCCC3)c12 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[cH;D2;+0:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:1:2.[NH4+;D0:11]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:10]:1:[c:9]:[c:8]:[#7;a:7]:[c;H0;D3;+0:6]:2-[NH2;D1;+0:11] | null | [] | null | null | null | null | The method described in Part J of Example 365 was used to oxidize and aminate 7-bromo-1-cylcohexylmethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline (7.58 g, 22.0 mmol). 3-Chloroperoxybenzoic acid (9.1 g of 50% pure material, 26.4 mmol) was added in five portions during the oxidation step, and the amination with ammonium... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.C1CCCCC1 | null | C(C)#N | null | null | CCOCc1nc2cnc3cc(Br)ccc3c2n1CC1CCCCC1.[NH4+]>C(C)#N>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-796b06cb40f64989bb91238e51ff606a | CC(C)CNc1c([N+](=O)[O-])cnc2cc(Br)ccc12>>CC(C)CNc1c(N)cnc2cc(Br)ccc12 | BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCC(C)C>>BrC1=CC=C2C(=C(C=NC2=C1)N)NCC(C)C | O=[N+:8]([O-])[c:7]1[c:6]([NH:5][CH2:4][CH:2]([CH3:1])[CH3:3])[c:17]2[c:11]([n:10][cH:9]1)[cH:12][c:13]([Br:14])[cH:15][cH:16]2>>[CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][c:6]1[c:7]([NH2:8])[cH:9][n:10][c:11]2[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]12 | CC(C)CNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 | CC(C)CNc1c(N)cnc2cc(Br)ccc12 | null | [Pt] | C1(=CC=CC=C1)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ncccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | null | [] | null | null | 8 | HOUR | (7-Bromo-3-nitroquinolin-4-yl)-(2-methylpropyl)amine (117 g) was dissolved in hot toluene (2 L) and poured into stainless steel Parr vessel. Additional toluene (2 L) and 5% platinum on carbon (12.5 g) were added. The vessel was evacuated, charged with hydrogen (54 psi, 3.7×105 Pa), and shaken overnight at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1 | Other | [Pt].C1(=CC=CC=C1)C | null | 8 | CC(C)CNc1c([N+](=O)[O-])cnc2cc(Br)ccc12>[Pt].C1(=CC=CC=C1)C>CC(C)CNc1c(N)cnc2cc(Br)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e8cfcc7d7bdb4706b163b70ba212038d | CC(C)CNc1c(N)cnc2cc(Br)ccc12.CCCC(=O)Cl>>CCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)C | C(CCC)(=O)Cl.BrC1=CC=C2C(=C(C=NC2=C1)N)NCC(C)C>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)C)CCC | [NH2:5][c:6]1[cH:7][n:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]2[c:16]1[NH:17][CH2:18][CH:19]([CH3:20])[CH3:21].O=[C:4](Cl)[CH2:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][n:8][c:9]3[cH:10][c:11]([Br:12])[cH:13][cH:14][c:15]3[c:16]2[n:17]1[CH2:18][CH:19]([CH3:20])[CH3:21] | CC(C)CNc1c(N)cnc2cc(Br)ccc12.CCCC(=O)Cl | CCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)C | null | [Au] | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 101a087a520f159c722ba3d78ed38f5c3c1cf154206e5edbeb1e6397c929560f | 56ef83dfadec35a1cf1db968b807e178cc4924ce15bf36d774883783cef0f450 | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C:4]-[C:5]-[n;H0;D3;+0:6]1:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[n;H0;D2;+0:13]:[c;H0;D3;+0:1]:1-[C:2]-[C:3] | null | [] | null | null | null | null | Butyryl chloride (1.1 equivalent) was slowly added to a stirred solution of 7-bromo-N4-(2-methylpropyl)quinoline-3,4-diamine (52.9 g, 0.18 mol.) in pyridine (700 mL) at room temperature. A pale yellow precipitate formed and then went into solution. The reaction mixture was heated at reflux for eight hours, and then all... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | HCl | [Au].N1=CC=CC=C1 | null | null | CC(C)CNc1c(N)cnc2cc(Br)ccc12.CCCC(=O)Cl>[Au].N1=CC=CC=C1>CCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-27bcffb2956c4abb8cb2439f0cab4e5f | CCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)C.[NH4+]>>CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C | C1(=CC=C(C=C1)S(=O)(=O)Cl)C.BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC(C)C)CCC.ClC=1C=C(C(=O)OO)C=CC1.[OH-].[NH4+]>>BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC(C)C)CCC | [CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[cH:7][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH:20]([CH3:21])[CH3:22].[NH4+:8]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[c:7]([NH2:8])[n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH:20]([CH3:21])[CH3:22] | CCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)C.[NH4+] | CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C | null | null | ClCCl | Functional Group Addition | OtherReaction | dc63235befaaf41df35292b6862b726098d8e1b79a2cef881f35b7cf9ff16606 | d69ce1fde4173969963123914389bef807fad83b73b8a587195a7122d5cdf1d2 | c1ccc2c(c1)ncc1nc[nH]c12 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[cH;D2;+0:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:1:2.[NH4+;D0:11]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:10]:1:[c:9]:[c:8]:[#7;a:7]:[c;H0;D3;+0:6]:2-[NH2;D1;+0:11] | null | [] | null | null | 15 | MINUTE | To a stirred solution of 7-bromo-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinoline (51.1 g, 0.148 mol) in dichloromethane (1 L) was slowly added 3-chloroperoxybenzoic acid (1.0 equivalent of 50% pure material) in small portions. The reaction was maintained at room temperature for one hour. Concentrated ammonium hy... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | null | ClCCl | null | 0.25 | CCCc1nc2cnc3cc(Br)ccc3c2n1CC(C)C.[NH4+]>ClCCl>CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f3deeef20851413a8d51142d4d2c4924 | C=C[B-](F)(F)F.CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C>>C=Cc1ccc2c(c1)nc(N)c1nc(CCC)n(CC(C)C)c12 | C(C)N(CC)CC.C(=C)[B-](F)(F)F.[K+].BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC(C)C)CCC.[OH-].[Na+]>>CC(CN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=C)N)CCC)C | F[B-](F)(F)[CH:2]=[CH2:1].Br[c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[n:9][c:10]([NH2:11])[c:12]1[n:13][c:14]([CH2:15][CH2:16][CH3:17])[n:18]([CH2:19][CH:20]([CH3:21])[CH3:22])[c:23]21>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[n:9][c:10]([NH2:11])[c:12]1[n:13][c:14]([CH2:15][CH2:16][CH3:17])[n:18]([CH2:19][CH:... | C=C[B-](F)(F)F.CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C | C=Cc1ccc2c(c1)nc(N)c1nc(CCC)n(CC(C)C)c12 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | C(CC)O.O | Functional Group Interconversion | OtherReaction | b6174e4193e02027d22a36dfa7ee1eca16a8f84c44e86ec780137145ed7eacc0 | 493c526dad91fdaab0a79ca6b28939f7e66256ca7a9e4efc8dfd07eebbd72256 | c1ccc2c(c1)ncc1nc[nH]c12 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[c:5](:[#7;a:6]):[c:7](:[#7;a:8]):[c:9]:[#7;a:10]:[c:11]:2:[c:12]:1.F-[B-](-F)(-F)-[CH;D2;+0:13]=[C;D1;H2:14]>>[#7;a:8]:[c:7]1:[c:9]:[#7;a:10]:[c:11]2:[c:12]:[c;H0;D3;+0:1](-[CH;D2;+0:13]=[C;D1;H2:14]):[c:2]:[c:3]:[c:4]:2:[c:5]:1:[#7;a:6] | null | [] | null | null | null | null | Triethylamine (3.0 equivalents), potassium vinyltrifluoroborate (1.0 equivalent) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.2 equivalent) were added to a solution of 7-bromo-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (1.0 equivalent) in n-propanol (30 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | Vinyl | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | Br-.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].C(CC)O.O | null | null | C=C[B-](F)(F)F.CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)C>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].C(CC)O.O>C=Cc1ccc2c(c1)nc(N)c1nc(CCC)n(CC(C)C)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a0b7a3a3e0674a5c922c7e18e8da34dc | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCOC.c1cn[nH]c1>>CCOCc1nc2c(N)nc3cc(-n4cccn4)ccc3c2n1CCCOC | P(=O)([O-])([O-])[O-].[K+].[K+].[K+].N1N=CC=C1.BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CCCOC)COCC.N[C@H]1[C@@H](CCCC1)N>>C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)N2N=CC=C2)N)N1)CCCOC | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:23]([CH2:24][CH2:25][CH2:26][O:27][CH3:28])[c:22]3[c:21]2[cH:20][cH:19]1.[nH:14]1[cH:15][cH:16][cH:17][n:18]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[n:14]4[cH:15][cH:16][cH:17][n:18]... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCOC.c1cn[nH]c1 | CCOCc1nc2c(N)nc3cc(-n4cccn4)ccc3c2n1CCCOC | null | [Cu]I | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 34efca80a73526f58805156846e0cfaa34d4d87fbfddf09fd49bf5f9e2f9ed6b | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1cnn(-c2ccc3c(c2)ncc2nc[nH]c23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.[#7;a:13]1:[c:14]:[c:15]:[c:16]:[nH;D2;+0:17]:1>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[n;H0;D3;+0:17]3:[#7;a:13]:[c:14]:[c:15]:[c:16]:3):[c:2]:[c:3]:2:[#7;a:4]:[c:5]:[c:6]:1:[#7;a:7] | 25 | [{"value": 25.0, "product": "C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)N2N=CC=C2)N)N1)CCCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15.5 | HOUR | A 4 dram vial containing a stir bar was charged sequentially with copper(I) iodide (0.038 g), potassium phosphate (0.890 g), pyrazole (0.164 g), 7-bromo-2-ethoxymethyl-1-(3-methoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine (0.786 g), (±)-trans-1,2-diaminocyclohexane (0.030 mL), and anhydrous 1,4-dioxane (2 mL). The vial... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2c(c1)ncc1[nH]cnc12.c1cn[nH]c1 | c1ccc2c(c1)ncc1[nH]cnc12.c1cn[nH]c1 | c1ccc2c(c1)ncc1[nH]cnc12.c1cn[nH]c1 | HBr | [Cu]I.O1CCOCC1 | null | 15.5 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCOC.c1cn[nH]c1>[Cu]I.O1CCOCC1>CCOCc1nc2c(N)nc3cc(-n4cccn4)ccc3c2n1CCCOC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5574c035cb5d4caf8df4dacdca15baab | COC(=O)C1CCOCC1.[NH4+]>>NC(=O)C1CCOCC1 | [OH-].[NH4+].O1CCC(CC1)C(=O)OC.[OH-].[NH4+]>>O1CCC(CC1)C(=O)N | CO[C:2](=[O:3])[CH:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1.[NH4+:1]>>[NH2:1][C:2](=[O:3])[CH:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1 | COC(=O)C1CCOCC1.[NH4+] | NC(=O)C1CCOCC1 | null | null | CO | Acylation | OtherReaction | d5b10d4f469e7a196a3b04a6a9e159a7d90514b6df5b50c1197d4b1b774c04e1 | adc0ef6f6c1340dd2dbab737c85bf17fc842769181c5db1a2b4f82b391b28f9f | C1CCOCC1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[NH4+;D0:6]>>[C:4]-[C:3](-[C;H0;D3;+0:1](-[NH2;D1;+0:6])=[O;D1;H0:2])-[C:5] | null | [] | null | null | 8 | HOUR | Ammonium hydroxide (1 L) was added to a solution of methyl tetrahydro-2H-pyran-4-carboxylate (20 mL, 150 mmol) in methanol (500 mL), and the reaction was stirred overnight at ambient temperature. Additional ammonium hydroxide (500 mL) was added, and the reaction was stirred for four additional days. The methanol was re... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary amide | null | null | C1CCOCC1 | HO- | CO | null | 8 | COC(=O)C1CCOCC1.[NH4+]>CO>NC(=O)C1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f146f725e49749349a288d4b0e2fcd92 | NCC1CCOCC1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCC1CCOCC1 | BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])Cl.O1CCC(CC1)CN>>BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCC1CCOCC1 | [NH2:15][CH2:16][CH:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1.Cl[c:14]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][n:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]21>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][n:6][c:7]2[cH:8][c:9]([Br:10])[cH:11][cH:12][c:13]2[c:14]1[NH:15][CH2:16][CH:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1 | NCC1CCOCC1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl | O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCC1CCOCC1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2c(NCC3CCOCC3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | 94.3 | [{"value": 94.3, "product": "BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCC1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The method described in Part E of Examples 431–436 was used to treat 7-bromo-4-chloro-3-nitroquinoline (12.43 g, 43.45 mmol) with C-(tetrahydropyran-4-yl)methylamine (10 g, 87 mmol) to provide 15.0 g of (7-bromo-3-nitroquinolin-4-yl)(tetrahydropyran-4-ylmethyl)amine as a bright yellow solid.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1.C1CCOCC1 | HCl | null | null | null | NCC1CCOCC1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>O=[N+]([O-])c1cnc2cc(Br)ccc2c1NCC1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eb25d8f7ee804c1381c56c9177ce0ca8 | CCOCc1nc2cnc3cc(Br)ccc3c2n1CC1CCOCC1.[NH4+]>>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCOCC1 | BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CC3CCOCC3)COCC.ClC=1C=C(C(=O)OO)C=CC1.[OH-].[NH4+].C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC3CCOCC3)COCC | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]3[c:18]2[n:19]1[CH2:20][CH:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1.[NH4+:9]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]3[c:18]2[n:19]1[CH2:20]... | CCOCc1nc2cnc3cc(Br)ccc3c2n1CC1CCOCC1.[NH4+] | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCOCC1 | null | ClC=1C=C(C(=O)OO)C=CC1 | C(C)#N | Functional Group Addition | OtherReaction | dc63235befaaf41df35292b6862b726098d8e1b79a2cef881f35b7cf9ff16606 | d69ce1fde4173969963123914389bef807fad83b73b8a587195a7122d5cdf1d2 | c1ccc2c(c1)ncc1ncn(CC3CCOCC3)c12 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[cH;D2;+0:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:1:2.[NH4+;D0:11]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:10]:1:[c:9]:[c:8]:[#7;a:7]:[c;H0;D3;+0:6]:2-[NH2;D1;+0:11] | null | [] | null | null | 8 | HOUR | The method described in Part J of Example 365 was used to oxidize and aminate 7-bromo-2-ethoxymethyl-1-(tetrahydropyran-4-ylmethyl)-1H-imidazo[4,5-c]quinoline (9.3 g, 23.0 mmol). 3-Chloroperoxybenzoic acid (7.9 g of 50% pure material, 23 mmol) was added in five portions during the oxidation step, which was stirred over... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.C1CCOCC1 | null | ClC=1C=C(C(=O)OO)C=CC1.C(C)#N | null | 8 | CCOCc1nc2cnc3cc(Br)ccc3c2n1CC1CCOCC1.[NH4+]>ClC=1C=C(C(=O)OO)C=CC1.C(C)#N>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-364907e077a64b9c904a0cc083c30353 | CC(C)Cn1cnc2c(N)nc3ccccc3c21.O=[N+]([O-])O>>CC(C)Cn1cnc2c(N)nc3ccc([N+](=O)[O-])cc3c21 | [OH-].[NH4+].CC(CN1C=NC=2C(=NC=3C=CC=CC3C21)N)C.[N+](=O)(O)[O-]>>CC(CN1C=NC=2C(=NC=3C=CC(=CC3C21)[N+](=O)[O-])N)C | [CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][cH:15][cH:19][c:20]3[c:21]12.O[N+:16](=[O:17])[O-:18]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][c:20]3[c:21]12 | CC(C)Cn1cnc2c(N)nc3ccccc3c21.O=[N+]([O-])O | CC(C)Cn1cnc2c(N)nc3ccc([N+](=O)[O-])cc3c21 | null | null | S(O)(O)(=O)=O | Functional Group Addition | Aromatic nitration with HNO3 | e5a0830ab7d7f820529ff7c5fca2a3f84f966182dcfb90bb0e8e19b90af481f5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc2c(c1)ncc1nc[nH]c12 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[#7;a:4]:[c:5]1:[c:6]:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]:1:[c:11]:[#7;a:12]>>[#7;a:4]:[c:5]1:[c:6]:[c:7]:[c;H0;D3;+0:8](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:9]:[c:10]:1:[c:11]:[#7;a:12] | null | [] | null | null | 2 | HOUR | A solution of 1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (28.3 g, 0.118 mol) in concentrated sulfuric acid (150 mL) was cooled to 5° C. A solution of 70% nitric acid (8.4 mL, 0.130 mol) in sulfuric acid (30 mL) was added in portions over a period of one hour. The reaction temperature was maintained below 10° ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1nc2ccccc2c2[nH]cnc12 | c1ccc2ncc3nc[nH]c3c2c1 | c1ccc2ncc3nc[nH]c3c2c1 | HO- | S(O)(O)(=O)=O | null | 2 | CC(C)Cn1cnc2c(N)nc3ccccc3c21.O=[N+]([O-])O>S(O)(O)(=O)=O>CC(C)Cn1cnc2c(N)nc3ccc([N+](=O)[O-])cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bdb211b4df684f309f1596fd2503ee77 | CC(C)Cn1cnc2c(N)nc3ccc(N)cc3c21.COC1CCC(OC)O1>>CC(C)Cn1cnc2c(N)nc3ccc(-n4cccc4)cc3c21 | COC1OC(CC1)OC.NC1=CC=2C3=C(C(=NC2C=C1)N)N=CN3CC(C)C>>CC(CN1C=NC=2C(=NC=3C=CC(=CC3C21)N2C=CC=C2)N)C | [CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][c:15]([NH2:16])[cH:21][c:22]3[c:23]12.CO[CH:17]1O[CH:20](OC)[CH2:19][CH2:18]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[c:9]([NH2:10])[n:11][c:12]3[cH:13][cH:14][c:15](-[n:16]4[cH:17][cH:18][cH:19][cH:20]4)[cH:21]... | CC(C)Cn1cnc2c(N)nc3ccc(N)cc3c21.COC1CCC(OC)O1 | CC(C)Cn1cnc2c(N)nc3ccc(-n4cccc4)cc3c21 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 0e9d22b0723ec2930c6f0b28cb06c2d86835df697b962917265b2a52889a76e9 | 37da407ba22aeb87f9320448e7710117027e549cd7c89e722598c54789c5481f | c1ccn(-c2ccc3ncc4nc[nH]c4c3c2)c1 | C-O-[CH;D3;+0:1]1-O-[CH;D3;+0:2](-O-C)-[CH2;D2;+0:3]-[CH2;D2;+0:4]-1.[#7;a:5]:[c:6]1:[c:7]:[c:8]:[c;H0;D3;+0:9](-[NH2;D1;+0:10]):[c:11]:[c:12]:1:[c:13]:[#7;a:14]>>[#7;a:5]:[c:6]1:[c:7]:[c:8]:[c;H0;D3;+0:9](-[n;H0;D3;+0:10]2:[cH;D2;+0:1]:[cH;D2;+0:4]:[cH;D2;+0:3]:[cH;D2;+0:2]:2):[c:11]:[c:12]:1:[c:13]:[#7;a:14] | 57.3 | [{"value": 57.3, "product": "CC(CN1C=NC=2C(=NC=3C=CC(=CC3C21)N2C=CC=C2)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 2,5-Dimethoxytetrahydrofuran (1.6 mL of 95%, 12 mmol) was added to a suspension of 8-amino-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine (3.0 g, 12 mmol) in acetic acid (60 mL), and the reaction was heated at reflux for one hour. The resulting dark brown solution was concentrated under reduced pressure, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Primary amine | null | C1CCOC1 | c1cc[nH]c1 | c1ccc2ncc3nc[nH]c3c2c1.c1cc[nH]c1 | HO- | C(C)(=O)O | null | 0.5 | CC(C)Cn1cnc2c(N)nc3ccc(N)cc3c21.COC1CCC(OC)O1>C(C)(=O)O>CC(C)Cn1cnc2c(N)nc3ccc(-n4cccc4)cc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b1f865ef25a04e39839832f0be237929 | CC1(C)OC(=O)C(=CNc2cccc(Br)c2)C(=O)O1>>Oc1ccnc2cc(Br)ccc12.Oc1ccnc2cccc(Br)c12 | BrC=1C=C(C=CC1)NC=C1C(OC(OC1=O)(C)C)=O>>BrC1=CC=C2C(=CC=NC2=C1)O.BrC1=C2C(=CC=NC2=CC=C1)O | O=[C:18]1O[C:14]([CH3:15])([CH3:20])[O:13][C:2](=[O:1])[C:3]1=[CH:4][NH:5][c:6]1[cH:7][c:8]([Br:9])[cH:10][cH:11][cH:12]1>>[OH:1][c:2]1[cH:3][cH:4][n:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][cH:11][c:12]12.[OH:13][c:14]1[cH:15][cH:16][n:17][c:18]2[cH:19][cH:20][cH:21][c:22]([Br:23])[c:24]12 | CC1(C)OC(=O)C(=CNc2cccc(Br)c2)C(=O)O1 | Oc1ccnc2cc(Br)ccc12.Oc1ccnc2cccc(Br)c12 | null | null | C1=CC=C(C=C1)C2=CC=CC=C2.C1=CC=C(C=C1)OC2=CC=CC=C2 | Aromatic Heterocycle Formation | OtherReaction | 5f75dae222d74bb9fc2b294b367403a07bdf8272477d1afc70174e15b1e90f5d | c37506458ef2b9e2def05ab89db5b266098a3ec74f2476e997b750208146ef63 | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | O=[C;H0;D3;+0:1]1-O-[C;H0;D4;+0:2](-[CH3;D1;+0:3])(-[CH3;D1;+0:4])-[O;H0;D2;+0:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[C;H0;D3;+0:8]-1=[CH;D2;+0:9]-[NH;D2;+0:10]-[c:11](:[c:12]):[cH;D2;+0:13]:[c:14]:[c:15]>>[OH;D1;+0:7]-[c;H0;D3;+0:6]1:[cH;D2;+0:8]:[cH;D2;+0:9]:[n;H0;D2;+0:10]:[c:11](:[c:12]):[c;H0;D3;+0:13]:1:[c:14]:[c:15... | null | [] | null | null | null | null | 5-[(3-Bromophenylamino)methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione (32.6 g, 0.100 mol) was heated at 250° C. in DOWTHERM A heat transfer fluid for one hour, and then the reaction was allowed to cool to ambient temperature. A precipitate formed upon cooling and was isolated by filtration and washed with diethyl ether... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ester.Ester | Aromatic halide.Aromatic alcohol.Aromatic alcohol | C1COCOC1.c1ccccc1 | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | c1ccc2ncccc2c1.c1ccc2ncccc2c1 | null | C1=CC=C(C=C1)C2=CC=CC=C2.C1=CC=C(C=C1)OC2=CC=CC=C2 | null | null | CC1(C)OC(=O)C(=CNc2cccc(Br)c2)C(=O)O1>C1=CC=C(C=C1)C2=CC=CC=C2.C1=CC=C(C=C1)OC2=CC=CC=C2>Oc1ccnc2cc(Br)ccc12.Oc1ccnc2cccc(Br)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-85819ad6c6834adb8e5accf545355994 | CC(C)CNc1c(N)cnc2cccc(Br)c12>>CC(C)Cn1cnc2cnc3cccc(Br)c3c21 | BrC1=C2C(=C(C=NC2=CC=C1)N)NCC(C)C.C(OCC)(OCC)OCC.Cl.N1=CC=CC=C1>>BrC=1C=2C3=C(C=NC2C=CC1)N=CN3CC(C)C | [CH3:1][CH:2]([CH3:3])[CH2:4][NH:5][c:18]1[c:8]([NH2:7])[cH:9][n:10][c:11]2[cH:12][cH:13][cH:14][c:15]([Br:16])[c:17]21>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[cH:9][n:10][c:11]3[cH:12][cH:13][cH:14][c:15]([Br:16])[c:17]3[c:18]12 | CC(C)CNc1c(N)cnc2cccc(Br)c12 | CC(C)Cn1cnc2cnc3cccc(Br)c3c21 | null | null | C(C)#N | Aromatic Heterocycle Formation | OtherReaction | eb766b33cc37973e90b0a06e1adfb35c78d598e09189e9099c509c7d0e4a7793 | c12bf4e666f812d0e692aca3756678364265d1c8b3469e9563c84f9ed1df94d2 | c1ccc2c(c1)ncc1nc[nH]c12 | [C:1]-[C:2]-[NH;D2;+0:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1-[NH2;D1;+0:10]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[c:11]:[n;H0;D2;+0:10]:[c:9]2:[c:8]:[#7;a:7]:[c:6]:[c:5]:[c:4]:2:1 | null | [] | null | null | null | null | A mixture of 5-bromo-N4-(2-methylpropyl)quinoline-3,4-diamine (1.0 g, 3.4 mmol), triethyl orthoformate (0.9 mL, 5 mmol), and pyridine hydrochloride (117 mg, 1.0 mmol) in acetonitrile (17 mL) was heated at reflux overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by HPF... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1cccc2ncc3nc[nH]c3c12 | c1cccc2ncc3nc[nH]c3c12 | Other | C(C)#N | null | null | CC(C)CNc1c(N)cnc2cccc(Br)c12>C(C)#N>CC(C)Cn1cnc2cnc3cccc(Br)c3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b7318fcfda094b7d96708957c22d1daf | CC(C)Cn1cnc2cnc3cccc(Br)c3c21.OB(O)c1ccccc1>>CC(C)Cn1cnc2cnc3cccc(-c4ccccc4)c3c21 | BrC=1C=2C3=C(C=NC2C=CC1)N=CN3CC(C)C.C1(=CC=CC=C1)B(O)O>>CC(CN1C=NC=2C=NC=3C=CC=C(C3C21)C2=CC=CC=C2)C | Br[c:15]1[cH:14][cH:13][cH:12][c:11]2[n:10][cH:9][c:8]3[n:7][cH:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:23]3[c:22]21.OB(O)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[cH:9][n:10][c:11]3[cH:12][cH:13][cH:14][c:15](-[c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21]4)[c:22]3[... | CC(C)Cn1cnc2cnc3cccc(Br)c3c21.OB(O)c1ccccc1 | CC(C)Cn1cnc2cnc3cccc(-c4ccccc4)c3c21 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 4ccbd71978726c37809efbeb35dc94765cb7edf530e87f54e6de7a8542442ba8 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3ncc4nc[nH]c4c23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]3:[#7;a:9]:[c:10]:[#7;a:11](-[C:12]):[c:13]:3:[c:14]:2:1.O-B(-O)-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19]>>[C:12]-[#7;a:11]1:[c:10]:[#7;a:9]:[c:8]2:[c:7]:[#7;a:6]:[c:5]3:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19]):... | null | [] | null | null | null | null | 9-Bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (0.34 mmol) and benzene boronic acid (62 mg, 0.51 mmol) were coupled according to Part J of Example 1. The work-up procedure described in Parts 125–135 was followed. The crude product was purified by HPFC (eluting with chloroform:CMA in a gradient from 100:0 to 85:1... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cccc2ncc3[nH]cnc3c12.c1ccccc1 | c1cccc2ncc3nc[nH]c3c12.c1ccccc1 | c1cccc2ncc3nc[nH]c3c12.c1ccccc1 | HBr.B | null | null | null | CC(C)Cn1cnc2cnc3cccc(Br)c3c21.OB(O)c1ccccc1>>CC(C)Cn1cnc2cnc3cccc(-c4ccccc4)c3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aa3baeb825a2493d835b1e3bfc26310b | CC(C)Cn1cnc2cnc3cccc(Br)c3c21.CCCOc1ccc(B(O)O)cc1>>CCCOc1ccc(-c2cccc3ncc4ncn(CC(C)C)c4c23)cc1 | BrC=1C=2C3=C(C=NC2C=CC1)N=CN3CC(C)C.C(CC)OC1=CC=C(C=C1)B(O)O>>CC(CN1C=NC=2C=NC=3C=CC=C(C3C21)C2=CC=C(C=C2)OCCC)C | Br[c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][cH:15][c:16]3[n:17][cH:18][n:19]([CH2:20][CH:21]([CH3:22])[CH3:23])[c:24]3[c:25]12.OB(O)[c:8]1[cH:7][cH:6][c:5]([O:4][CH2:3][CH2:2][CH3:1])[cH:27][cH:26]1>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]3[n:14][cH:15][c:16]4[n:17][cH:18][n:... | CC(C)Cn1cnc2cnc3cccc(Br)c3c21.CCCOc1ccc(B(O)O)cc1 | CCCOc1ccc(-c2cccc3ncc4ncn(CC(C)C)c4c23)cc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | 7641a7375c485375c827a1b7fc577b96303c9dfd51153d2ecc4afa14501f7686 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccc3ncc4nc[nH]c4c23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[c:8]3:[#7;a:9]:[c:10]:[#7;a:11](-[C:12]):[c:13]:3:[c:14]:2:1.O-B(-O)-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19]>>[C:12]-[#7;a:11]1:[c:10]:[#7;a:9]:[c:8]2:[c:7]:[#7;a:6]:[c:5]3:[c:4]:[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19]):... | 90 | [{"value": 90.0, "product": "CC(CN1C=NC=2C=NC=3C=CC=C(C3C21)C2=CC=C(C=C2)OCCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 9-Bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (1.0 g, 3.4 mmol) and 4-propoxyphenylboronic acid (1.0 g, 5.5 mmol) were coupled according to Part J of Example 1. The palladium (II) acetate (2.5 mg, 0.011 mmol) was added as a 5 mg/mL solution in toluene. The work-up procedure described in Parts 125–135 was follow... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cccc2ncc3[nH]cnc3c12.c1ccccc1 | c1ccccc1.c1cccc2ncc3[nH]cnc3c12 | c1ccccc1.c1cccc2ncc3[nH]cnc3c12 | HBr.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C | null | null | CC(C)Cn1cnc2cnc3cccc(Br)c3c21.CCCOc1ccc(B(O)O)cc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C>CCCOc1ccc(-c2cccc3ncc4ncn(CC(C)C)c4c23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5de5ae4e1a584a48b0d2e3a218983a7a | CC#N.CCCOc1ccc(-c2cccc3ncc4ncn(CC(C)C)c4c23)cc1>>CCCOc1ccc(-c2cccc3nc(N)c4ncn(CC(C)C)c4c23)cc1 | CC(CN1C=NC=2C=NC=3C=CC=C(C3C21)C2=CC=C(C=C2)OCCC)C.C(C)#N>>CC(CN1C=NC=2C(=NC=3C=CC=C(C3C21)C2=CC=C(C=C2)OCCC)N)C | CC#[N:16].[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]3[n:14][cH:15][c:17]4[n:18][cH:19][n:20]([CH2:21][CH:22]([CH3:23])[CH3:24])[c:25]4[c:26]23)[cH:27][cH:28]1>>[CH3:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]3[n:14][c:15]([NH2:16])[c:17]4[n:1... | CC#N.CCCOc1ccc(-c2cccc3ncc4ncn(CC(C)C)c4c23)cc1 | CCCOc1ccc(-c2cccc3nc(N)c4ncn(CC(C)C)c4c23)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 668eaaeddba370e0966e8df58804fb8e09839e55608e92b00099a5ce100ab0ef | 807c02e8854fa1d85bad1ac2ebd73d5cdddf0728c08cb10c1d1278b952c720d7 | c1ccc(-c2cccc3ncc4nc[nH]c4c23)cc1 | C-C#[N;H0;D1;+0:1].[C:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[c:6]2:[cH;D2;+0:7]:[#7;a:8]:[c:9]:[c:10]:[c:11]:1:2>>[C:2]-[#7;a:3]1:[c:4]:[#7;a:5]:[c:6]2:[c:11]:1:[c:10]:[c:9]:[#7;a:8]:[c;H0;D3;+0:7]:2-[NH2;D1;+0:1] | null | [] | null | null | 36 | HOUR | The method described in Part J of Example 365 was used to oxidize and aminate 1-(2-methylpropyl)-9-(4-propoxyphenyl)-1H-imidazo[4,5-c]quinoline (1.1 g, 3.1 mmol). The amination reaction was stirred for 36 hours. The crude product was purified by HPFC (eluting with chloroform:CMA in a gradient from 100:0 to 70:30) to pr... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | c1cccc2ncc3[nH]cnc3c12 | c1nc2ccccc2c2nc[nH]c12 | c1ccccc1.c1nc2ccccc2c2nc[nH]c12 | Other | null | null | 36 | CC#N.CCCOc1ccc(-c2cccc3ncc4ncn(CC(C)C)c4c23)cc1>>CCCOc1ccc(-c2cccc3nc(N)c4ncn(CC(C)C)c4c23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0789ae86abcc4ffcb54afb54fb83337e | CCOC(=O)CC(=O)OCC.Nc1ccccc1Br>>O=C(O)CC(=O)Nc1ccccc1Br | Cl.C(CC(=O)OCC)(=O)OCC.BrC1=C(N)C=CC=C1.C([O-])([O-])=O.[Na+].[Na+]>>BrC1=C(C=CC=C1)NC(CC(=O)O)=O | CCO[C:5]([CH2:4][C:2](=[O:1])[O:3]CC)=[O:6].[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[Br:14]>>[O:1]=[C:2]([OH:3])[CH2:4][C:5](=[O:6])[NH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[Br:14] | CCOC(=O)CC(=O)OCC.Nc1ccccc1Br | O=C(O)CC(=O)Nc1ccccc1Br | null | null | CO.O | Protection | OtherReaction | 70293d3e8c18e2b6da68ed11b9d6823c24895b8790c14ff32c8b49ced3b12880 | 29fbc6ece4ea5207c4566380f45c4382f2be045c119b517d772f85d11bb512cc | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-C-C.[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[O;D1;H0:5]=[C:4](-[OH;D1;+0:6])-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10] | 57.3 | [{"value": 57.3, "product": "BrC1=C(C=CC=C1)NC(CC(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | null | null | Diethyl malonate (101 mL, 0.989 mol) and 2-bromoaniline (50.g, 0.291 mol) were combined and heated at 180° C. for six hours. A Dean-Stark trap was used to collect the volatiles. The reaction was allowed to cool to ambient temperature overnight; a precipitate formed. The precipitate was isolated by filtration and combin... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Carboxylic acid.Secondary amide | null | null | c1ccccc1 | HO- | CO.O | 180 | null | CCOC(=O)CC(=O)OCC.Nc1ccccc1Br>CO.O>O=C(O)CC(=O)Nc1ccccc1Br |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-69f9ed9971d84108bc0b47b3fce1fc7f | O=C(O)CC(=O)Nc1ccccc1Br>>Oc1cc(O)c2cccc(Br)c2n1 | BrC1=C(C=CC=C1)NC(CC(=O)O)=O.[OH-].[Na+]>>BrC=1C=CC=C2C(=CC(=NC12)O)O | O=[C:4]([CH2:3][C:2](=[O:1])[NH:13][c:12]1[cH:6][cH:7][cH:8][cH:9][c:10]1[Br:11])[OH:5]>>[OH:1][c:2]1[cH:3][c:4]([OH:5])[c:6]2[cH:7][cH:8][cH:9][c:10]([Br:11])[c:12]2[n:13]1 | O=C(O)CC(=O)Nc1ccccc1Br | Oc1cc(O)c2cccc(Br)c2n1 | null | null | Cl | Aromatic Heterocycle Formation | OtherReaction | 9402a7279b29c9d8a731ecc3a1fcf489e5f1179eb567486aae94c816493d85b5 | 999d168235ae1f4640223947c418a4f3e4605c0e33d865b4a7894f9b30606573 | c1ccc2ncccc2c1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-[NH;D2;+0:6]-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[O;D1;H1:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[OH;D1;+0:5]):[n;H0;D2;+0:6]:[c:7](:[c:8]):[c;H0;D3;+0:9]:1:[c:10]:[c:11] | 91.6 | [{"value": 91.6, "product": "BrC=1C=CC=C2C(=CC(=NC12)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 4 | HOUR | N-(2-Bromophenyl)malonamic acid (43 g, 170 mmol), polyphosphoric acid (334 mL of 0.5 M), and hydrochloric acid (444 mL of 1 N) were combined and heated at 140° C. for three hours. The solution was allowed to cool to ambient temperature, and additional hydrochloric acid (603 mL of 1 N) was added. The reaction was stirre... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amide | Aromatic alcohol.Aromatic alcohol | c1ccccc1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | Cl | 140 | 4 | O=C(O)CC(=O)Nc1ccccc1Br>Cl>Oc1cc(O)c2cccc(Br)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c8d5b04d3fab4744a5a52f1cf07989d7 | O=[N+]([O-])O.Oc1cc(O)c2cccc(Br)c2n1>>O=[N+]([O-])c1c(O)nc2c(Br)cccc2c1O | BrC=1C=CC=C2C(=CC(=NC12)O)O.[N+](=O)(O)[O-].[N+](=O)(O)[O-]>>BrC=1C=CC=C2C(=C(C(=NC12)O)[N+](=O)[O-])O | O[N+:2](=[O:1])[O-:3].[cH:4]1[c:5]([OH:6])[n:7][c:8]2[c:9]([Br:10])[cH:11][cH:12][cH:13][c:14]2[c:15]1[OH:16]>>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([OH:6])[n:7][c:8]2[c:9]([Br:10])[cH:11][cH:12][cH:13][c:14]2[c:15]1[OH:16] | O=[N+]([O-])O.Oc1cc(O)c2cccc(Br)c2n1 | O=[N+]([O-])c1c(O)nc2c(Br)cccc2c1O | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 93c60f395fb4f0e5be7b3c9f5aae0bbd322ad57344c0d8df26b336a54b906179 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccc2ncccc2c1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H1:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9](-[O;D1;H1:10]):[cH;D2;+0:11]:1>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:11]1:[c:5](-[O;D1;H1:4]):[c:6]:[c:7]:[#7;a:8]:[c:9]:1-[O;D1;H1:10] | 63.9 | [{"value": 63.9, "product": "BrC=1C=CC=C2C(=C(C(=NC12)O)[N+](=O)[O-])O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A modification of the method described in Part D of Example 10 was used to treat 8-bromoquinoline-2,4-diol (10.0 g, 41.6 mmol) with nitric acid (3.6 mL of 11.74 M, 54 mmol). The nitric acid was added at ambient temperature, and then the reaction was heated at 100° C. for one hour, at which time an exotherm occurred. Th... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HO- | null | 100 | null | O=[N+]([O-])O.Oc1cc(O)c2cccc(Br)c2n1>>O=[N+]([O-])c1c(O)nc2c(Br)cccc2c1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e4bc21a062524818a009f89c7b32cc59 | CC(C)(O)CNc1c(N)c(Cl)nc2c(Br)cccc12.CCOCC(=O)Cl>>CCOCc1nc2cnc3c(Br)cccc3c2n1CC(C)(C)O | NC=1C(=NC2=C(C=CC=C2C1NCC(C)(O)C)Br)Cl.C(C)OCC(=O)Cl.C(C)O.C([O-])([O-])=O.[K+].[K+]>>BrC1=CC=CC=2C3=C(C=NC12)N=C(N3CC(C)(O)C)COCC | Cl[c:8]1[c:7]([NH2:6])[c:17]([NH:18][CH2:19][C:20]([CH3:21])([CH3:22])[OH:23])[c:16]2[c:10]([n:9]1)[c:11]([Br:12])[cH:13][cH:14][cH:15]2.O=[C:5](Cl)[CH2:4][O:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[c:11]([Br:12])[cH:13][cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][C:20]([CH3:21])([... | CC(C)(O)CNc1c(N)c(Cl)nc2c(Br)cccc12.CCOCC(=O)Cl | CCOCc1nc2cnc3c(Br)cccc3c2n1CC(C)(C)O | null | null | ClCCl.O | Aromatic Heterocycle Formation | OtherReaction | d3d842fa118f2e7920c947aa6ef1a06fae09ab9b42d5d738d2e92f8b7b692f55 | bb5ef43dc5e52681475802be44587bc64e5a88f0c1c4eb737da942a7bc33c68c | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[#8:3].Cl-[c;H0;D3;+0:4]1:[#7;a:5]:[c:6]:[c:7]:[c:8](-[NH;D2;+0:9]-[C:10]-[C:11]):[c:12]:1-[NH2;D1;+0:13]>>[#8:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:13]:[c:12]2:[cH;D2;+0:4]:[#7;a:5]:[c:6]:[c:7]:[c:8]:2:[n;H0;D3;+0:9]:1-[C:10]-[C:11] | 80.8 | [{"value": 80.8, "product": "BrC1=CC=CC=2C3=C(C=NC12)N=C(N3CC(C)(O)C)COCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 36 | HOUR | A solution of 1-(3-amino-8-bromo-2-chloroquinolin-4-ylamino)-2-methylpropan-2-ol (4.65 g, 14.4 mmol) and ethoxyacetyl chloride (1.9 mL, 15.8 mmol) in dichloromethane (72 mL) was stirred for one hour at ambient temperature. The solvent was removed under reduced pressure, and ethanol (43 mL), water (29 mL), and potassium... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic halide.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1nc2c(cnc3ccccc32)[nH]1 | c1nc2c(cnc3ccccc32)[nH]1 | HCl | ClCCl.O | 40 | 36 | CC(C)(O)CNc1c(N)c(Cl)nc2c(Br)cccc12.CCOCC(=O)Cl>ClCCl.O>CCOCc1nc2cnc3c(Br)cccc3c2n1CC(C)(C)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6ce4ecf087dd4b5e9dfdb947815f2d30 | CC1(C)OC[C@@H](CN)O1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>CC1(C)OC[C@@H](CNc2c([N+](=O)[O-])cnc3cc(Br)ccc23)O1 | BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])Cl.CC1(OC[C@H](O1)CN)C>>BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NC[C@H]1OC(OC1)(C)C | [CH3:1][C:2]1([CH3:3])[O:4][CH2:5][C@@H:6]([CH2:7][NH2:8])[O:23]1.Cl[c:9]1[c:10]([N+:11](=[O:12])[O-:13])[cH:14][n:15][c:16]2[cH:17][c:18]([Br:19])[cH:20][cH:21][c:22]12>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][C@@H:6]([CH2:7][NH:8][c:9]2[c:10]([N+:11](=[O:12])[O-:13])[cH:14][n:15][c:16]3[cH:17][c:18]([Br:19])[cH:20][cH:21]... | CC1(C)OC[C@@H](CN)O1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl | CC1(C)OC[C@@H](CNc2c([N+](=O)[O-])cnc3cc(Br)ccc23)O1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2c(NC[C@@H]3COCO3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[#8:10]-[C:11]-[C:12]-[NH2;D1;+0:13]>>[#7;+:3]-[c:2]1:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:1]:1-[NH;D2;+0:13]-[C:12]-[C:11]-[#8:10] | 88.4 | [{"value": 88.4, "product": "BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NC[C@H]1OC(OC1)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-Bromo-4-chloro-3-nitroquinoline (22.00 g, 76.52 mmol) was treated with (R)-2,2-dimethyl-1,3-dioxolane-4-methanamine (11.61 g, 114.8 mmol) according to the method described in Part A of Examples 152–156. The crude product was triturated with water (200 mL), isolated by filtration, washed with water, dried, and suspend... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | C1COCO1.c1ccc2ncccc2c1 | HCl | null | null | null | CC1(C)OC[C@@H](CN)O1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>CC1(C)OC[C@@H](CNc2c([N+](=O)[O-])cnc3cc(Br)ccc23)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ebe61890eb1d414990c24c6f5dd8ad09 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1C[C@@H]1COC(C)(C)O1.OB(O)c1cccnc1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1C[C@@H]1COC(C)(C)O1 | BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3C[C@H]3OC(OC3)(C)C)COCC.N1=CC(=CC=C1)B(O)O>>CC1(OC[C@H](O1)CN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC)C | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:24]([CH2:25][C@@H:26]4[CH2:27][O:28][C:29]([CH3:30])([CH3:31])[O:32]4)[c:23]3[c:22]2[cH:21][cH:20]1.OB(O)[c:14]1[cH:15][cH:16][cH:17][n:18][cH:19]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:1... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1C[C@@H]1COC(C)(C)O1.OB(O)c1cccnc1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1C[C@@H]1COC(C)(C)O1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | d23a08b59b246d837a860414fc085402a8d785d2b981e3447d503da913f098ed | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1cncc(-c2ccc3c(c2)ncc2ncn(C[C@@H]4COCO4)c23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.O-B(-O)-[c;H0;D3;+0:13]1:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:1>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13]3:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:3):[c:2]:[c:3]:2:[#7;a:4]:[c:5]:[c:6]:1... | 65.5 | [{"value": 65.5, "product": "CC1(OC[C@H](O1)CN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (R)-7-Bromo-1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (3.0 g, 6.9 mmol) and pyridine-3-boronic acid (1.02 g, 8.27 mmol) were coupled according to the method described in Examples 118–121. The work-up procedure described in Part F of Examples 125–135 was followed. The cr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1.C1COCO1 | HBr.B | null | null | null | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1C[C@@H]1COC(C)(C)O1.OB(O)c1cccnc1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1C[C@@H]1COC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-81e1d7ec4fba449c82d78b037813b515 | CC1(C)OC[C@H](CN)O1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>CC1(C)OC[C@H](CNc2c([N+](=O)[O-])cnc3cc(Br)ccc23)O1 | BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])Cl.CC1(OC[C@@H](O1)CN)C.C(C)O>>BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NC[C@@H]1OC(OC1)(C)C | [CH3:1][C:2]1([CH3:3])[O:4][CH2:5][C@H:6]([CH2:7][NH2:8])[O:23]1.Cl[c:9]1[c:10]([N+:11](=[O:12])[O-:13])[cH:14][n:15][c:16]2[cH:17][c:18]([Br:19])[cH:20][cH:21][c:22]12>>[CH3:1][C:2]1([CH3:3])[O:4][CH2:5][C@H:6]([CH2:7][NH:8][c:9]2[c:10]([N+:11](=[O:12])[O-:13])[cH:14][n:15][c:16]3[cH:17][c:18]([Br:19])[cH:20][cH:21][c... | CC1(C)OC[C@H](CN)O1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl | CC1(C)OC[C@H](CNc2c([N+](=O)[O-])cnc3cc(Br)ccc23)O1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2c(NC[C@H]3COCO3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[#8:10]-[C:11]-[C:12]-[NH2;D1;+0:13]>>[#7;+:3]-[c:2]1:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:1]:1-[NH;D2;+0:13]-[C:12]-[C:11]-[#8:10] | 96.1 | [{"value": 96.1, "product": "BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NC[C@@H]1OC(OC1)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-Bromo-4-chloro-3-nitroquinoline (11.00 g, 38.26 mmol) was reacted with (S)-2,2-dimethyl-[1,3]dioxolane-4-methanamine (5.81 g, 57.4 mmol) according to the method described in Part A of Examples 125–135. When the reaction was complete, it was concentrated under reduced pressure, and the residue was stirred with water (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | C1COCO1.c1ccc2ncccc2c1 | HCl | ClCCl | null | null | CC1(C)OC[C@H](CN)O1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>ClCCl>CC1(C)OC[C@H](CNc2c([N+](=O)[O-])cnc3cc(Br)ccc23)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-24769b0edb5146748dcf7bf5bec69837 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1C[C@H]1COC(C)(C)O1.c1cncc(B2OCCCO2)c1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1C[C@H]1COC(C)(C)O1 | BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3C[C@@H]3OC(OC3)(C)C)COCC.B1(OCCCO1)C2=CN=CC=C2>>CC1(OC[C@@H](O1)CN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC)C | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:24]([CH2:25][C@H:26]4[CH2:27][O:28][C:29]([CH3:30])([CH3:31])[O:32]4)[c:23]3[c:22]2[cH:21][cH:20]1.C1COB([c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)OC1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12]... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1C[C@H]1COC(C)(C)O1.c1cncc(B2OCCCO2)c1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1C[C@H]1COC(C)(C)O1 | null | null | null | C-C Coupling | Suzuki coupling with boronic esters | 2cd1cbe6f17c98cb5223a75d20dfc144a6eae8461c4fe8a7e9cc4bc7ecadb166 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1cncc(-c2ccc3c(c2)ncc2ncn(C[C@H]4COCO4)c23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.C1-C-O-B(-[c;H0;D3;+0:13]2:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:2)-O-C-1>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13]3:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:3):[c:2]:[c:3]:2:[#7;a:4]:[c:5... | 54.2 | [{"value": 54.2, "product": "CC1(OC[C@@H](O1)CN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (S)-7-Bromo-1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (2.65 g, 6.09 mmol) and pyridine-3-boronic acid 1,3-propanediol cyclic ester (1.19 g, 7.30 mmol) were coupled according to the method described in Examples 118–121. The work-up procedure described in Part F of Exampl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2c(c1)ncc1[nH]cnc12.B1OCCCO1.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1.C1COCO1 | HBr.B | null | null | null | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1C[C@H]1COC(C)(C)O1.c1cncc(B2OCCCO2)c1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1C[C@H]1COC(C)(C)O1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-440aa7395e284f75ac4d4d96d14f7675 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCCCN1C(=O)OC(C)(C)C.c1cncc(B2OCCCO2)c1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCCCN1C(=O)OC(C)(C)C | NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC2N(CCCC2)C(=O)OC(C)(C)C)COCC)Br.B1(OCCCO1)C2=CN=CC=C2>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC2N(CCCC2)C(=O)OC(C)(C)C)COCC)C=2C=NC=CC2 | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:24]([CH2:25][CH:26]4[CH2:27][CH2:28][CH2:29][CH2:30][N:31]4[C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])[c:23]3[c:22]2[cH:21][cH:20]1.C1COB([c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)OC1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCCCN1C(=O)OC(C)(C)C.c1cncc(B2OCCCO2)c1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCCCN1C(=O)OC(C)(C)C | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | null | C-C Coupling | Suzuki coupling with boronic esters | 2cd1cbe6f17c98cb5223a75d20dfc144a6eae8461c4fe8a7e9cc4bc7ecadb166 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1cncc(-c2ccc3c(c2)ncc2ncn(CC4CCCCN4)c23)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.C1-C-O-B(-[c;H0;D3;+0:13]2:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:2)-O-C-1>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13]3:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:3):[c:2]:[c:3]:2:[#7;a:4]:[c:5... | 70.8 | [{"value": 70.8, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC2N(CCCC2)C(=O)OC(C)(C)C)COCC)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | tert-Butyl 2-[(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate (4.82 g, 9.30 mmol) and pyridine-3-boronic acid 1,3-propanediol cyclic ester (1.67 g, 10.2 mmol) were coupled according to the method described in Part F of Example 414. Palladium (II) acetate (0.0103 f, 0.046 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2c(c1)ncc1[nH]cnc12.B1OCCCO1.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1.C1CC[NH]CC1 | HBr.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | null | null | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCCCN1C(=O)OC(C)(C)C.c1cncc(B2OCCCO2)c1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-]>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCCCN1C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-46965b52963f4a0b906c2734dfbd92bc | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCCCN1.CS(=O)(=O)Cl>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCCCN1S(C)(=O)=O | CS(=O)(=O)Cl.Cl.Cl.Cl.C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)C=2C=NC=CC2)N)N1)CC1NCCCC1.C(C)N(CC)CC.CS(=O)(=O)Cl>>C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)C=2C=NC=CC2)N)N1)CC1N(CCCC1)S(=O)(=O)C | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][cH:17][n:18][cH:19]4)[cH:20][cH:21][c:22]3[c:23]2[n:24]1[CH2:25][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][NH:31]1.Cl[S:32]([CH3:33])(=[O:34])=[O:35]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][... | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCCCN1.CS(=O)(=O)Cl | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCCCN1S(C)(=O)=O | null | null | C(Cl)(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | d63e07b47df62aebedb35134f6d0504cfcbed5ccfdec31c2c42bba6875c15fe7 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | c1cncc(-c2ccc3c(c2)ncc2ncn(CC4CCCCN4)c23)c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6](-[C:7])-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:5]-[C:6](-[C:7])-[N;H0;D3;+0:8](-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:9]-[C:10] | 34.9 | [{"value": 34.9, "product": "C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)C=2C=NC=CC2)N)N1)CC1N(CCCC1)S(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 2-ethoxymethyl-1-(piperidin-2-ylmethyl)-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine trihydrochloride (0.60 g, 1.1 mmol) and triethylamine (0.79 mL, 5.7 mmol) in chloroform (50 mL) was cooled to 4° C. Methanesulfonyl chloride (0.12 mL, 1.5 mmol) was added, and the reaction was allowed to warm to amb... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1.C1CC[NH]CC1 | HCl | C(Cl)(Cl)Cl | null | 8 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCCCN1.CS(=O)(=O)Cl>C(Cl)(Cl)Cl>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CC1CCCCN1S(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e290789573584e50a29ba8fd5e830722 | CC(C)(C)OC(=O)NCc1ccc(CN)cc1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>CC(C)(C)OC(=O)NCc1ccc(CNc2c([N+](=O)[O-])cnc3cc(Br)ccc23)cc1 | C(=O)(OC(C)(C)C)NCC1=CC=C(C=C1)CN.BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])Cl.C(C)N(CC)CC>>C(C)(C)(C)OC(NCC1=CC=C(C=C1)CNC1=C(C=NC2=CC(=CC=C12)Br)[N+](=O)[O-])=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][NH2:15])[cH:30][cH:31]1.Cl[c:16]1[c:17]([N+:18](=[O:19])[O-:20])[cH:21][n:22][c:23]2[cH:24][c:25]([Br:26])[cH:27][cH:28][c:29]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([CH... | CC(C)(C)OC(=O)NCc1ccc(CN)cc1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl | CC(C)(C)OC(=O)NCc1ccc(CNc2c([N+](=O)[O-])cnc3cc(Br)ccc23)cc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccnc3ccccc23)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2](-[#7;+:3]):[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9].[NH2;D1;+0:10]-[C:11]-[c:12]>>[#7;+:3]-[c:2]1:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8](:[c:9]):[c;H0;D3;+0:1]:1-[NH;D2;+0:10]-[C:11]-[c:12] | 93.4 | [{"value": 93.4, "product": "C(C)(C)(C)OC(NCC1=CC=C(C=C1)CNC1=C(C=NC2=CC(=CC=C12)Br)[N+](=O)[O-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 1-(N-BOC-aminomethyl)-4-(aminomethyl)benzene (5.0 g, 21 mmol) in dichloromethane (50 mL) was added dropwise to a mixture of 7-bromo-4-chloro-3-nitroquinoline (5.81 g, 20 mmol) and triethylamine (5.63 mL) in dichloromethane (60 mL). The reaction was stirred for 16 hours and then washed sequentially with water and satura... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HCl | ClCCl | null | 16 | CC(C)(C)OC(=O)NCc1ccc(CN)cc1.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>ClCCl>CC(C)(C)OC(=O)NCc1ccc(CNc2c([N+](=O)[O-])cnc3cc(Br)ccc23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e14b4f690e7d423e92497dc07775b581 | CC(C)(C)OC(=O)NCc1ccc(CNc2c([N+](=O)[O-])cnc3cc(Br)ccc23)cc1>>CC(C)(C)OC(=O)NCc1ccc(CNc2c(N)cnc3cc(Br)ccc23)cc1 | C([O-])([O-])=O.[K+].[K+].S(=O)([O-])S(=O)[O-].[Na+].[Na+].C(C)(C)(C)OC(NCC1=CC=C(C=C1)CNC1=C(C=NC2=CC(=CC=C12)Br)[N+](=O)[O-])=O>>C(C)(C)(C)OC(NCC1=CC=C(C=C1)CNC1=C(C=NC2=CC(=CC=C12)Br)N)=O | O=[N+:18]([O-])[c:17]1[c:16]([NH:15][CH2:14][c:13]2[cH:12][cH:11][c:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:29][cH:28]2)[c:27]2[c:21]([n:20][cH:19]1)[cH:22][c:23]([Br:24])[cH:25][cH:26]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][c:10]1[cH:11][cH:12][c:13]([CH2:14][NH:1... | CC(C)(C)OC(=O)NCc1ccc(CNc2c([N+](=O)[O-])cnc3cc(Br)ccc23)cc1 | CC(C)(C)OC(=O)NCc1ccc(CNc2c(N)cnc3cc(Br)ccc23)cc1 | null | CC[N+]1=CC=C(C=C1)C2=CC=[N+](C=C2)CC.[Br-].[Br-] | ClCCl.O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(CNc2ccnc3ccccc23)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | 100.5 | [{"value": 100.5, "product": "C(C)(C)(C)OC(NCC1=CC=C(C=C1)CNC1=C(C=NC2=CC(=CC=C12)Br)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | HOUR | Ethyl viologen dibromide (0.069 g, 0.18 mmol), potassium carbonate (12.76 g, 92 mmol) in water (55mL), and sodium hydrosulfite (11.25 g, 65 mmol) in water (55mL) were added sequentially to a solution of tert-butyl{4-[(7-bromo-3-nitroquinolin-4-ylamino)methyl]benzyl}carbamate (9.0 g, 18.5 mmol) in dichloromethane (110 m... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccc2ncccc2c1 | Other | CC[N+]1=CC=C(C=C1)C2=CC=[N+](C=C2)CC.[Br-].[Br-].ClCCl.O | null | 20 | CC(C)(C)OC(=O)NCc1ccc(CNc2c([N+](=O)[O-])cnc3cc(Br)ccc23)cc1>CC[N+]1=CC=C(C=C1)C2=CC=[N+](C=C2)CC.[Br-].[Br-].ClCCl.O>CC(C)(C)OC(=O)NCc1ccc(CNc2c(N)cnc3cc(Br)ccc23)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8944d4bc581b4c2091b717fc29f8e6a3 | CC(C)(C)OC(=O)NCc1ccc(CNc2c(N)cnc3cc(Br)ccc23)cc1.CCOCC(=O)Cl>>CCOCc1nc2cnc3cc(Br)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1 | NC=1C=NC2=CC(=CC=C2C1NCC1=CC=C(CNC(OC(C)(C)C)=O)C=C1)Br.C(C)N(CC)CC.C(C)OCC(=O)Cl>>C(C)(C)(C)OC(NCC1=CC=C(C=C1)CN1C(=NC=2C=NC=3C=C(C=CC3C21)Br)COCC)=O | [NH2:6][c:7]1[cH:8][n:9][c:10]2[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]2[c:17]1[NH:18][CH2:19][c:20]1[cH:21][cH:22][c:23]([CH2:24][NH:25][C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[cH:33][cH:34]1.O=[C:5](Cl)[CH2:4][O:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c... | CC(C)(C)OC(=O)NCc1ccc(CNc2c(N)cnc3cc(Br)ccc23)cc1.CCOCC(=O)Cl | CCOCc1nc2cnc3cc(Br)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | 101a087a520f159c722ba3d78ed38f5c3c1cf154206e5edbeb1e6397c929560f | 56ef83dfadec35a1cf1db968b807e178cc4924ce15bf36d774883783cef0f450 | c1ccc(Cn2cnc3cnc4ccccc4c32)cc1 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[#8:3].[NH2;D1;+0:4]-[c:5]1:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:1-[NH;D2;+0:11]-[C:12]-[c:13]>>[#8:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c:5]2:[c:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:2:[n;H0;D3;+0:11]:1-[C:12]-[c:13] | 35 | [{"value": 35.0, "product": "C(C)(C)(C)OC(NCC1=CC=C(C=C1)CN1C(=NC=2C=NC=3C=C(C=CC3C21)Br)COCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | tert-Butyl {4-[(3-amino-7-bromoquinolin-4-ylamino)methyl]benzyl}carbamate (8.46 g, 18.5 mmol), triethylamine (2.25 mL) and dichloromethane (92 mL) were combined. Ethoxyacetyl chloride (2.92 g, 24 mmol) was added dropwise to the mixture. The reaction was stirred for an additional 1.5 hours and then concentrated under re... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | HCl | ClCCl | null | 1.5 | CC(C)(C)OC(=O)NCc1ccc(CNc2c(N)cnc3cc(Br)ccc23)cc1.CCOCC(=O)Cl>ClCCl>CCOCc1nc2cnc3cc(Br)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-aa8698d39a6b418ab64bf6c776047c64 | CCOCc1nc2cnc3cc(Br)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1.[NH4+]>>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1 | C1(=CC=C(C=C1)S(=O)(=O)Cl)C.ClC=1C=C(C(=O)OO)C=CC1.C(C)(C)(C)OC(NCC1=CC=C(C=C1)CN1C(=NC=2C=NC=3C=C(C=CC3C21)Br)COCC)=O.[OH-].[NH4+]>>C(C)(C)(C)OC(NCC1=CC=C(C=C1)CN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)COCC)=O | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]3[c:18]2[n:19]1[CH2:20][c:21]1[cH:22][cH:23][c:24]([CH2:25][NH:26][C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[cH:34][cH:35]1.[NH4+:9]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11... | CCOCc1nc2cnc3cc(Br)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1.[NH4+] | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1 | null | null | C(Cl)(Cl)Cl | Functional Group Addition | OtherReaction | dc63235befaaf41df35292b6862b726098d8e1b79a2cef881f35b7cf9ff16606 | d69ce1fde4173969963123914389bef807fad83b73b8a587195a7122d5cdf1d2 | c1ccc(Cn2cnc3cnc4ccccc4c32)cc1 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[cH;D2;+0:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:1:2.[NH4+;D0:11]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:10]:1:[c:9]:[c:8]:[#7;a:7]:[c;H0;D3;+0:6]:2-[NH2;D1;+0:11] | null | [] | null | null | 1 | HOUR | 3-Chloroperoxybenzoic acid (2.91 g, 9.3 mmol, 55% pure) was added to a solution of tert-butyl[4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-ylmethyl)benzyl]carbamate (3.2 g, 6.1 mmol) in chloroform (60 mL). The reaction was stirred for 1 hour and then cooled with an ice bath. Ammonium hydroxide (40 mL) was adde... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | null | C(Cl)(Cl)Cl | null | 1 | CCOCc1nc2cnc3cc(Br)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1.[NH4+]>C(Cl)(Cl)Cl>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-730080668d58495bb46b128bad4a9aa6 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1.c1cncc(B2OCCCO2)c1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1 | C(C)(C)(C)OC(NCC1=CC=C(C=C1)CN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)COCC)=O.B1(OCCCO1)C2=CN=CC=C2.C([O-])([O-])=O.[Na+].[Na+].C(CC)O>>C(C)(C)(C)OC(NCC1=CC=C(C=C1)CN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC)=O | Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:24]([CH2:25][c:26]4[cH:27][cH:28][c:29]([CH2:30][NH:31][C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])[cH:39][cH:40]4)[c:23]3[c:22]2[cH:21][cH:20]1.C1COB([c:14]2[cH:15][cH:16][cH:17][n:18][cH:19]2)OC1>>[CH3:1][CH2:2][O:3]... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1.c1cncc(B2OCCCO2)c1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1 | null | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | O | C-C Coupling | Suzuki coupling with boronic esters | 2cd1cbe6f17c98cb5223a75d20dfc144a6eae8461c4fe8a7e9cc4bc7ecadb166 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc(Cn2cnc3cnc4cc(-c5cccnc5)ccc4c32)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.C1-C-O-B(-[c;H0;D3;+0:13]2:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:2)-O-C-1>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13]3:[c:14]:[c:15]:[c:16]:[#7;a:17]:[c:18]:3):[c:2]:[c:3]:2:[#7;a:4]:[c:5... | 64.1 | [{"value": 64.1, "product": "C(C)(C)(C)OC(NCC1=CC=C(C=C1)CN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 105 | CELSIUS | null | null | tert-Butyl[4-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-ylmethyl)benzyl]carbamate (1.15 g, 2.1 mmol), triphenylphosphine (0.005 g), pyridine-3-boronic acid 1,3-propanediol cyclic ester (0.365 g, 2.2 mmol), and n-propanol (3.67 mL) were combined. Aqueous sodium carbonate (2M, 1.12 mL) and water (0.6 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2c(c1)ncc1[nH]cnc12.B1OCCCO1.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1.c1ccccc1 | HBr.B | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O | 105 | null | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1.c1cncc(B2OCCCO2)c1>C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4c2681be703e4a42a213e914545c842e | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1Cc1ccc(CN)cc1 | NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC2=CC=C(CNC(OC(C)(C)C)=O)C=C2)COCC)C=2C=NC=CC2>>NCC1=CC=C(CN2C(=NC=3C(=NC=4C=C(C=CC4C32)C=3C=NC=CC3)N)COCC)C=C1 | CC(C)(C)OC(=O)[NH:31][CH2:30][c:29]1[cH:28][cH:27][c:26]([CH2:25][n:24]2[c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:6][c:7]3[c:8]([NH2:9])[n:10][c:11]4[cH:12][c:13](-[c:14]5[cH:15][cH:16][cH:17][n:18][cH:19]5)[cH:20][cH:21][c:22]4[c:23]32)[cH:33][cH:32]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[c... | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1Cc1ccc(CN)cc1 | null | null | Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(Cn2cnc3cnc4cc(-c5cccnc5)ccc4c32)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[c:3]>>[NH2;D1;+0:1]-[C:2]-[c:3] | 97.9 | [{"value": 97.9, "product": "NCC1=CC=C(CN2C(=NC=3C(=NC=4C=C(C=CC4C32)C=3C=NC=CC3)N)COCC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | tert-Butyl {4-[4-amino-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-ylmethyl]benzyl}carbamate (0.660 g) was added to ethanolic hydrogen chloride (4M, 10 mL) and the solution was heated at reflux temperature for 30 minutes. The reaction was cooled to room temperature and concentrated under reduced pressur... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1.c1ccccc1 | HO- | Cl | null | null | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1Cc1ccc(CNC(=O)OC(C)(C)C)cc1>Cl>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1Cc1ccc(CN)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eb0c87782d154fc1a5d50dcca884829e | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1Cc1ccc(CN)cc1.CS(=O)(=O)Cl>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1Cc1ccc(CNS(C)(=O)=O)cc1 | CS(=O)(=O)Cl.NCC1=CC=C(CN2C(=NC=3C(=NC=4C=C(C=CC4C32)C=3C=NC=CC3)N)COCC)C=C1.C([O-])([O-])=O.[Na+].[Na+]>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC2=CC=C(CNS(=O)(=O)C)C=C2)COCC)C=2C=NC=CC2 | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][cH:17][n:18][cH:19]4)[cH:20][cH:21][c:22]3[c:23]2[n:24]1[CH2:25][c:26]1[cH:27][cH:28][c:29]([CH2:30][NH2:31])[cH:36][cH:37]1.Cl[S:32]([CH3:33])(=[O:34])=[O:35]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH... | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1Cc1ccc(CN)cc1.CS(=O)(=O)Cl | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1Cc1ccc(CNS(C)(=O)=O)cc1 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccc(Cn2cnc3cnc4cc(-c5cccnc5)ccc4c32)cc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[C:6]-[c:7]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[C:6]-[c:7] | 38.7 | [{"value": 38.7, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC2=CC=C(CNS(=O)(=O)C)C=C2)COCC)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Methanesulfonyl chloride (0.13 mL, 1.7 mmol) was added dropwise to a mixture of 1-(4-aminomethylbenzyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine (0.520 g, 1.2 mmol) in dichloromethane (10 mL). The reaction was stirred for 16 hours and then saturated aqueous sodium carbonate was added. The layer... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1.c1ccccc1 | HCl | ClCCl | null | 16 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1Cc1ccc(CN)cc1.CS(=O)(=O)Cl>ClCCl>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1Cc1ccc(CNS(C)(=O)=O)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e6aae422c5174d3cb16088d3a37e9cb7 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCN.CN(C)CCOC(c1ccccc1)c1ccc(C(=O)O)cc1>>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCNC(=O)c1ccc(C(OCCN(C)C)c2ccccc2)cc1 | CN(CCOC(C1=CC=C(C(=O)O)C=C1)C1=CC=CC=C1)C.ON1N=NC2=C1C=CC=C2.NCCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)C=2C=NC=CC2)N)COCC.Cl.CN(CCCN=C=NCC)C>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNC(C2=CC=C(C=C2)C(C2=CC=CC=C2)OCCN(C)C)=O)COCC)C=2C=NC=CC2 | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](-[c:14]4[cH:15][cH:16][cH:17][n:18][cH:19]4)[cH:20][cH:21][c:22]3[c:23]2[n:24]1[CH2:25][CH2:26][CH2:27][CH2:28][NH2:29].O[C:30](=[O:31])[c:32]1[cH:33][cH:34][c:35]([CH:36]([O:37][CH2:38][CH2:39][N:40]([CH3:41])[CH3:42])[c:43]2[cH:44][cH... | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCN.CN(C)CCOC(c1ccccc1)c1ccc(C(=O)O)cc1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCNC(=O)c1ccc(C(OCCN(C)C)c2ccccc2)cc1 | null | null | CC(=O)N(C)C.C(Cl)(Cl)Cl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCCCn1cnc2cnc3cc(-c4cccnc4)ccc3c21)c1ccc(Cc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 61.9 | [{"value": 61.9, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNC(C2=CC=C(C=C2)C(C2=CC=CC=C2)OCCN(C)C)=O)COCC)C=2C=NC=CC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A mixture of 4-[(2-dimethylaminoethoxy)phenylmethyl]benzoic acid (0.433 g) and 1-hydroxybenzotriazole (0.196 g) in chloroform (7 mL) was cooled to 0° C. and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.277 g) was added in small portions over a 2 minute period. The mixture was stirred for 1 hour and th... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1.c1ccccc1.c1ccccc1 | HO- | CC(=O)N(C)C.C(Cl)(Cl)Cl | 0 | 1 | CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCN.CN(C)CCOC(c1ccccc1)c1ccc(C(=O)O)cc1>CC(=O)N(C)C.C(Cl)(Cl)Cl>CCOCc1nc2c(N)nc3cc(-c4cccnc4)ccc3c2n1CCCCNC(=O)c1ccc(C(OCCN(C)C)c2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a763b5a33d5f4a50b6f144f670dad872 | NCCN.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>>NCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 | BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])Cl.C(CN)N>>BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCN | [NH2:1][CH2:2][CH2:3][NH2:4].Cl[c:5]1[c:6]([N+:7](=[O:8])[O-:9])[cH:10][n:11][c:12]2[cH:13][c:14]([Br:15])[cH:16][cH:17][c:18]12>>[NH2:1][CH2:2][CH2:3][NH:4][c:5]1[c:6]([N+:7](=[O:8])[O-:9])[cH:10][n:11][c:12]2[cH:13][c:14]([Br:15])[cH:16][cH:17][c:18]12 | NCCN.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl | NCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2](:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]:[c:8]:1-[#7;+:9].[C:10]-[C:11]-[NH2;D1;+0:12]>>[#7;+:9]-[c:8]1:[c:7]:[#7;a:6]:[c:4](:[c:5]):[c:2](:[c:3]):[c;H0;D3;+0:1]:1-[NH;D2;+0:12]-[C:11]-[C:10] | null | [] | null | null | 8 | HOUR | A solution of 7-bromo-4-chloro-3-nitroquinoline (143.8 g, 0.5 mol) in 800 mL warm DMF was added to a stirred solution of ethylenediamine in 200 mL DMF at room temperature; the reaction was stirred at room temperature overnight. The reaction was quenched with 2 L water and stirred for an additional hour. Additional wate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | CN(C)C=O | null | 8 | NCCN.O=[N+]([O-])c1cnc2cc(Br)ccc2c1Cl>CN(C)C=O>NCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b33109869e254d76aed04997a8636ff6 | CS(=O)(=O)NCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12>>CS(=O)(=O)NCCNc1c(N)cnc2cc(Br)ccc12 | BrC1=CC=C2C(=C(C=NC2=C1)[N+](=O)[O-])NCCNS(=O)(=O)C>>NC=1C=NC2=CC(=CC=C2C1NCCNS(=O)(=O)C)Br | O=[N+:11]([O-])[c:10]1[c:9]([NH:8][CH2:7][CH2:6][NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[c:20]2[c:14]([n:13][cH:12]1)[cH:15][c:16]([Br:17])[cH:18][cH:19]2>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][CH2:6][CH2:7][NH:8][c:9]1[c:10]([NH2:11])[cH:12][n:13][c:14]2[cH:15][c:16]([Br:17])[cH:18][cH:19][c:20]12 | CS(=O)(=O)NCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12 | CS(=O)(=O)NCCNc1c(N)cnc2cc(Br)ccc12 | null | [Pt] | C(C)#N | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2ncccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6] | null | [] | null | null | 8 | HOUR | An 8 L stainless steel Parr vessel was charged with N-[2-(7-bromo-3-nitroquinolin-4-ylamino)ethyl]methanesulfonamide (61 g), 5% Pt/C catalyst (6.0 g) and acetonitrile (3 L). The vessel was evacuated, filled with hydrogen (45 psi, 3.1×105 Pa), and shaken at ambient temperature overnight. The reaction mixture was filtere... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncccc2c1 | Other | [Pt].C(C)#N | null | 8 | CS(=O)(=O)NCCNc1c([N+](=O)[O-])cnc2cc(Br)ccc12>[Pt].C(C)#N>CS(=O)(=O)NCCNc1c(N)cnc2cc(Br)ccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ab7b1d1d5bf34e299a5c6ee23d6d3cfb | CCCCC(=O)Cl.CS(=O)(=O)NCCNc1c(N)cnc2cc(Br)ccc12>>CCCCc1nc2cnc3cc(Br)ccc3c2n1CCNS(C)(=O)=O | NC=1C=NC2=CC(=CC=C2C1NCCNS(=O)(=O)C)Br.C(CCCC)(=O)Cl>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCNS(=O)(=O)C)CCCC | O=[C:5](Cl)[CH2:4][CH2:3][CH2:2][CH3:1].[NH2:6][c:7]1[cH:8][n:9][c:10]2[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]2[c:17]1[NH:18][CH2:19][CH2:20][NH:21][S:22]([CH3:23])(=[O:24])=[O:25]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20... | CCCCC(=O)Cl.CS(=O)(=O)NCCNc1c(N)cnc2cc(Br)ccc12 | CCCCc1nc2cnc3cc(Br)ccc3c2n1CCNS(C)(=O)=O | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 101a087a520f159c722ba3d78ed38f5c3c1cf154206e5edbeb1e6397c929560f | 56ef83dfadec35a1cf1db968b807e178cc4924ce15bf36d774883783cef0f450 | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C:4]-[C:5]-[n;H0;D3;+0:6]1:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[n;H0;D2;+0:13]:[c;H0;D3;+0:1]:1-[C:2]-[C:3] | null | [] | null | null | 1.5 | HOUR | To a stirred solution of N-[2-(3-amino-7-bromoquinolin-4-ylamino)ethyl]methanesulfonamide (46.4 g, 0.129 mol) in 1000 mL pyridine was slowly added valeryl chloride (1.1 equivalents). After 1.5 hours the mixture was yellow and turbid. The reaction mixture was then heated at reflux for 12 hours, allowed to cool to ambien... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | HCl | N1=CC=CC=C1 | null | 1.5 | CCCCC(=O)Cl.CS(=O)(=O)NCCNc1c(N)cnc2cc(Br)ccc12>N1=CC=CC=C1>CCCCc1nc2cnc3cc(Br)ccc3c2n1CCNS(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-633c6df4f26b4aa19b24d536d897844f | CCCCc1nc2cnc3cc(Br)ccc3c2n1CCNS(C)(=O)=O.[NH4+]>>CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCNS(C)(=O)=O | C1(=CC=C(C=C1)S(=O)(=O)Cl)C.ClC=1C=C(C(=O)OO)C=CC1.BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCNS(=O)(=O)C)CCCC.C([O-])([O-])=O.[K+].[K+].[OH-].[NH4+]>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCNS(=O)(=O)C)CCCC)Br | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]3[c:18]2[n:19]1[CH2:20][CH2:21][NH:22][S:23]([CH3:24])(=[O:25])=[O:26].[NH4+:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]3[c:18]2[n:19]1[CH2... | CCCCc1nc2cnc3cc(Br)ccc3c2n1CCNS(C)(=O)=O.[NH4+] | CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCNS(C)(=O)=O | null | null | ClCCl.O | Functional Group Addition | OtherReaction | dc63235befaaf41df35292b6862b726098d8e1b79a2cef881f35b7cf9ff16606 | d69ce1fde4173969963123914389bef807fad83b73b8a587195a7122d5cdf1d2 | c1ccc2c(c1)ncc1nc[nH]c12 | [C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[cH;D2;+0:6]:[#7;a:7]:[c:8]:[c:9]:[c:10]:1:2.[NH4+;D0:11]>>[C:1]-[#7;a:2]1:[c:3]:[#7;a:4]:[c:5]2:[c:10]:1:[c:9]:[c:8]:[#7;a:7]:[c;H0;D3;+0:6]:2-[NH2;D1;+0:11] | null | [] | null | null | 2 | HOUR | 3-Chloroperoxybenzoic acid (1.0 equivalent of 50% pure material) was added to a solution of N-[2-(7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide (44 g, 103.4 mmol) in 1000 mL dichloromethane. After 2 hours, concentrated ammonium hydroxide solution (600 mL) was added. The reaction was stirred fo... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | null | ClCCl.O | null | 2 | CCCCc1nc2cnc3cc(Br)ccc3c2n1CCNS(C)(=O)=O.[NH4+]>ClCCl.O>CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCNS(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3930a4c368c440b2ab323231484fcfea | C=C[B-](F)(F)F.CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCNS(C)(=O)=O>>C=Cc1ccc2c(c1)nc(N)c1nc(CCCC)n(CCNS(C)(=O)=O)c12 | NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCNS(=O)(=O)C)CCCC)Br.C(=C)[B-](F)(F)F.[K+]>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCNS(=O)(=O)C)CCCC)C=C | F[B-](F)(F)[CH:2]=[CH2:1].Br[c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[n:9][c:10]([NH2:11])[c:12]1[n:13][c:14]([CH2:15][CH2:16][CH2:17][CH3:18])[n:19]([CH2:20][CH2:21][NH:22][S:23]([CH3:24])(=[O:25])=[O:26])[c:27]21>>[CH2:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[n:9][c:10]([NH2:11])[c:12]1[n:13][c:14]([CH2:15][CH2:1... | C=C[B-](F)(F)F.CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCNS(C)(=O)=O | C=Cc1ccc2c(c1)nc(N)c1nc(CCCC)n(CCNS(C)(=O)=O)c12 | null | null | null | Functional Group Interconversion | OtherReaction | b6174e4193e02027d22a36dfa7ee1eca16a8f84c44e86ec780137145ed7eacc0 | 493c526dad91fdaab0a79ca6b28939f7e66256ca7a9e4efc8dfd07eebbd72256 | c1ccc2c(c1)ncc1nc[nH]c12 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[c:5](:[#7;a:6]):[c:7](:[#7;a:8]):[c:9]:[#7;a:10]:[c:11]:2:[c:12]:1.F-[B-](-F)(-F)-[CH;D2;+0:13]=[C;D1;H2:14]>>[#7;a:8]:[c:7]1:[c:9]:[#7;a:10]:[c:11]2:[c:12]:[c;H0;D3;+0:1](-[CH;D2;+0:13]=[C;D1;H2:14]):[c:2]:[c:3]:[c:4]:2:[c:5]:1:[#7;a:6] | null | [] | null | null | null | null | N-[2-(4-Amino-7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]methanesulfonamide was coupled with potassium vinyltrifluoroborate according to the procedure described in Part D of Examples 440–455 and recrystallized from acetonitrile to provide N-[2-(4-amino-2-butyl-7-vinyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]meth... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | Vinyl | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | Br-.B | null | null | null | C=C[B-](F)(F)F.CCCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCNS(C)(=O)=O>>C=Cc1ccc2c(c1)nc(N)c1nc(CCCC)n(CCNS(C)(=O)=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9312b9100a3448fd880c4a1e4f95c690 | CCCNC(=O)NCCNc1c(N)cnc2cc(Br)ccc12.CCOCC(=O)Cl>>CCCNC(=O)NCCn1c(COCC)nc2cnc3cc(Br)ccc3c21 | NC=1C=NC2=CC(=CC=C2C1NCCNC(=O)NCCC)Br.C(C)OCC(=O)Cl>>BrC=1C=CC=2C3=C(C=NC2C1)N=C(N3CCNC(=O)NCCC)COCC | [CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[NH:7][CH2:8][CH2:9][NH:10][c:27]1[c:17]([NH2:16])[cH:18][n:19][c:20]2[cH:21][c:22]([Br:23])[cH:24][cH:25][c:26]21.O=[C:11](Cl)[CH2:12][O:13][CH2:14][CH3:15]>>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[NH:7][CH2:8][CH2:9][n:10]1[c:11]([CH2:12][O:13][CH2:14][CH3:15])[n:16][c:17]2[cH... | CCCNC(=O)NCCNc1c(N)cnc2cc(Br)ccc12.CCOCC(=O)Cl | CCCNC(=O)NCCn1c(COCC)nc2cnc3cc(Br)ccc3c21 | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 092888ef5709db41360ea7e61766d8be84b90a21a3bf7772e6af19a215999134 | 56ef83dfadec35a1cf1db968b807e178cc4924ce15bf36d774883783cef0f450 | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[C;H0;D3;+0:1](=O)-[C:2]-[#8:3].[C:4]-[C:5]-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[#8:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:13]:[c:12]2:[c:11]:[#7;a:10]:[c:9]:[c:8]:[c:7]:2:[n;H0;D3;+0:6]:1-[C:5]-[C:4] | null | [] | 80 | CELSIUS | 1.5 | HOUR | To a stirred solution of 1-[2-(3-amino-7-bromoquinolin-4-ylamino)ethyl]-3-(2-methylethyl)urea (27.2 g, 0.0743 mol) in 600 mL pyridine was slowly added ethoxyacetyl chloride (1.1 equivalents). After 1.5 hours the mixture was yellow and turbid. The reaction mixture was then heated at 80° C. for 12 hours and then concentr... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine.Secondary amine | null | c1ccc2ncccc2c1 | c1ccc2c(c1)ncc1nc[nH]c12 | c1ccc2c(c1)ncc1nc[nH]c12 | HCl | N1=CC=CC=C1 | 80 | 1.5 | CCCNC(=O)NCCNc1c(N)cnc2cc(Br)ccc12.CCOCC(=O)Cl>N1=CC=CC=C1>CCCNC(=O)NCCn1c(COCC)nc2cnc3cc(Br)ccc3c21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-02f3772b166949dc9620d2ef20591eba | C=Cc1ccccn1.CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCOC>>CCOCc1nc2c(N)nc3cc(/C=C/c4ccccn4)ccc3c2n1CCCOC | C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C.C(C)N(CC)CC.C(=C)C1=NC=CC=C1.BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CCCOC)COCC>>C(C)OCC=1N(C2=C(C(=NC=3C=C(C=CC23)\C=C\C2=NC=CC=C2)N)N1)CCCOC | [CH2:14]=[CH:15][c:16]1[cH:17][cH:18][cH:19][cH:20][n:21]1.Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:26]([CH2:27][CH2:28][CH2:29][O:30][CH3:31])[c:25]3[c:24]2[cH:23][cH:22]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13](/[CH:14]=[CH:... | C=Cc1ccccn1.CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCOC | CCOCc1nc2c(N)nc3cc(/C=C/c4ccccn4)ccc3c2n1CCCOC | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C1(=CC=CC=C1)C | C-C Coupling | Heck terminal vinyl | 17b6ed2dfc150cdb58934d18ea4782cc332e8e1eab0cb0866f204b219967b10e | 4b186811a4930853b446d93d9faa39b267bddb9ce0b8021bda5c5a3b2bc69f0b | C(=C/c1ccccn1)\c1ccc2c(c1)ncc1nc[nH]c12 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.[#7;a:13]:[c:14]-[C:15]=[CH2;D1;+0:16]>>[#7;a:13]:[c:14]/[C:15]=[CH;D2;+0:16]/[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1 | null | [] | 120 | CELSIUS | null | null | A thick walled glass tube, equipped with magnetic stir-bar, was charged with toluene (20 mL/g), palladium (II) acetate (0.1 equivalents), tri-ortho-tolylphosphine (0.3 equivalents), triethylamine (3.0 equivalents), 2-vinylpyridine (1.0 equivalent), and 7-bromo-2-ethoxymethyl-1-(3-methoxypropyl)-1H-imidazo[4,5-c]quinoli... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Vinyl | null | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccncc1 | HBr | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C | 120 | null | C=Cc1ccccn1.CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCOC>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C>CCOCc1nc2c(N)nc3cc(/C=C/c4ccccn4)ccc3c2n1CCCOC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-80cf92620b04461a88045e5db197cc1b | CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)OC(C)(C)C>>CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN | Cl.NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNC(OC(C)(C)C)=O)CCC)Br.[OH-].[Na+]>>NCCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)CCC | CC(C)(C)OC(=O)[NH:23][CH2:22][CH2:21][CH2:20][CH2:19][n:18]1[c:4]([CH2:3][CH2:2][CH3:1])[n:5][c:6]2[c:7]([NH2:8])[n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]21>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[c:7]([NH2:8])[n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][CH2:... | CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)OC(C)(C)C | CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN | null | null | C(C)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc2c(c1)ncc1nc[nH]c12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | 30 | MINUTE | Concentrated hydrochloric acid (˜15 mL) was added to a suspension of tert-butyl [4-(4-amino-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate (3.19 g, 6.7 mmol) in ethanol (6.4 mL), and the reaction was stirred for 30 minutes. The reaction was adjusted to pH 13 with the addition of 50% aqueous sodium hydr... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)ncc1[nH]cnc12 | HO- | C(C)O | null | 0.5 | CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)OC(C)(C)C>C(C)O>CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e76e69c5bfb14c809cb53c5b0ed0f7aa | CC(C)N=C=O.CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN>>CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)NC(C)C | C(C)(C)N=C=O.C(C)(C)N=C=O.NCCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)CCC.C(C)(C)N=C=O>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNC(=O)NC(C)C)CCC)Br | [C:24](=[O:25])=[N:26][CH:27]([CH3:28])[CH3:29].[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[c:7]([NH2:8])[n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][CH2:21][CH2:22][NH2:23]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[c:7]([NH2:8])[n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c... | CC(C)N=C=O.CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN | CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)NC(C)C | null | null | C(Cl)(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc2c(c1)ncc1nc[nH]c12 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:4]-[C:2](-[C;D1;H3:1])-[C;D1;H3:3] | 81.4 | [{"value": 81.4, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNC(=O)NC(C)C)CCC)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A suspension of 1-(4-aminobutyl)-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 5.3 mmol) in chloroform (20 mL) was cooled to 0° C., and a solution of isopropyl isocyanate (5.3 mmol) in chloroform (3 mL/g) was added slowly over a period of eight minutes. After one hour, additional isopropyl isocyanate (0.5... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2c(c1)ncc1[nH]cnc12 | null | C(Cl)(Cl)Cl | 0 | 1 | CC(C)N=C=O.CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN>C(Cl)(Cl)Cl>CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)NC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8ff2852322ff44bfbfb34c188b4e6d7d | CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN.O=C(Cl)C1CCCC1>>CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)C1CCCC1 | NCCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)CCC.C(C)N(CC)CC.C1(CCCC1)C(=O)Cl>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNC(=O)C2CCCC2)CCC)Br | [CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[c:7]([NH2:8])[n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][CH2:21][CH2:22][NH2:23].Cl[C:24](=[O:25])[CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30]1>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[c:7]([NH2:8])[n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:1... | CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN.O=C(Cl)C1CCCC1 | CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)C1CCCC1 | null | null | C(Cl)(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCCn1cnc2cnc3ccccc3c21)C1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5] | 49.9 | [{"value": 49.9, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNC(=O)C2CCCC2)CCC)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A suspension of 1-(4-aminobutyl)-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (2.42 g, 6.4 mmol) and triethylamine (0.99 mL, 7.1 mmol) in chloroform (240 mL) was cooled to 0° C., and cyclopentanecarbonyl chloride (0.78 mL, 6.4 mmol) was added dropwise over a period of five minutes. The reaction was stirred for te... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)ncc1[nH]cnc12.C1CCCC1 | HCl | C(Cl)(Cl)Cl | 0 | null | CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN.O=C(Cl)C1CCCC1>C(Cl)(Cl)Cl>CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)C1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d181d92d4be45a0a6fa4f4664e4e646 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCNCC1.O=C(Cl)N1CCOCC1>>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCN(C(=O)N2CCOCC2)CC1 | Cl.Cl.BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC3CCNCC3)COCC.C(C)N(CC)CC.N1(CCOCC1)C(=O)Cl>>BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC3CCN(CC3)C(=O)N3CCOCC3)COCC | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]3[c:18]2[n:19]1[CH2:20][CH:21]1[CH2:22][CH2:23][NH:24][CH2:33][CH2:34]1.Cl[C:25](=[O:26])[N:27]1[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCNCC1.O=C(Cl)N1CCOCC1 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCN(C(=O)N2CCOCC2)CC1 | null | null | C(Cl)(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | 2f6d0cf68900b13baad66104d6931c4ea135cb252da038c5d876a65827ece4fa | 353c6e1db25433862a8bcf26ca332f6abeb45cb685806584bc65f8cfcb712540 | O=C(N1CCOCC1)N1CCC(Cn2cnc3cnc4ccccc4c32)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5])-[C:9]-[C:10] | 84.6 | [{"value": 84.6, "product": "BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC3CCN(CC3)C(=O)N3CCOCC3)COCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 7-bromo-2-ethoxymethyl-1-(piperidin-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride (4.0 g, 8.1 mmol) and triethylamine (5.67 mL, 40.7 mmol) in chloroform (300 mL) was cooled to 0° C., and 4-morpholinecarbonyl chloride (0.95 mL, 8.1 mmol) was added dropwise. The reaction was allowed to warm ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Tertiary amide.Secondary amine | Urea | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2c(c1)ncc1[nH]cnc12.C1CC[NH]CC1.C1COCC[NH]1 | HCl | C(Cl)(Cl)Cl | null | 8 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCNCC1.O=C(Cl)N1CCOCC1>C(Cl)(Cl)Cl>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCN(C(=O)N2CCOCC2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-15a5760ecf63496191c81786fd202801 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)OC(C)(C)C>>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN | [OH-].[Na+].C([O-])(O)=O.[Na+].Cl.C(C)(C)(C)OC(NCCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)COCC)=O>>NCCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)COCC | CC(C)(C)OC(=O)[NH:24][CH2:23][CH2:22][CH2:21][CH2:20][n:19]1[c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]3[c:18]21>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]3[c:18]2[n:19]1[CH2:20][... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)OC(C)(C)C | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN | null | null | C(Cl)(Cl)Cl.O.O1CCOCC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc2c(c1)ncc1nc[nH]c12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 70.3 | [{"value": 70.3, "product": "NCCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)COCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Hydrogen chloride (100 mL of a 4 M solution in 1,4-dioxane) was added to tert-butyl[4-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate (10.0 g, 20.3 mmol), and the reaction was stirred for one hour. The reaction was adjusted to pH 11 with the addition of sodium hydroxide pellets in a small... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2c(c1)ncc1[nH]cnc12 | HO- | C(Cl)(Cl)Cl.O.O1CCOCC1 | null | 1 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)OC(C)(C)C>C(Cl)(Cl)Cl.O.O1CCOCC1>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e45af154c4a434dbd1369dfd3e515cd | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN.CS(=O)(=O)Cl>>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNS(C)(=O)=O | [OH-].[Na+].CS(=O)(=O)Cl.NCCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)COCC.C(C)N(CC)CC>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNS(=O)(=O)C)COCC)Br | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]3[c:18]2[n:19]1[CH2:20][CH2:21][CH2:22][CH2:23][NH2:24].Cl[S:25]([CH3:26])(=[O:27])=[O:28]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]3[c:... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN.CS(=O)(=O)Cl | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNS(C)(=O)=O | null | null | C(Cl)(Cl)Cl.O | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 120.6 | [{"value": 120.6, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNS(=O)(=O)C)COCC)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Methanesulfonyl chloride (0.44 mL, 5.7 mmol) was added to a suspension of 1-(4-aminobutyl)-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (2.04 g, 5.2 mmol) and triethylamine (0.94 mL, 6.8 mmol) in chloroform (100 mL), and the reaction was stirred for four hours. Water was added; a precipitate formed. The aqu... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2c(c1)ncc1[nH]cnc12 | HCl | C(Cl)(Cl)Cl.O | null | 4 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN.CS(=O)(=O)Cl>C(Cl)(Cl)Cl.O>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNS(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0094d8a37a7a4e47843d835197d1b45e | CC(C)N=C=O.CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN>>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)NC(C)C | NCCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)COCC.C(C)(C)N=C=O>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNC(=O)NC(C)C)COCC)Br | [C:25](=[O:26])=[N:27][CH:28]([CH3:29])[CH3:30].[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]3[c:18]2[n:19]1[CH2:20][CH2:21][CH2:22][CH2:23][NH2:24]>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:... | CC(C)N=C=O.CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)NC(C)C | null | null | C(Cl)(Cl)Cl | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | c1ccc2c(c1)ncc1nc[nH]c12 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[N;H0;D2;+0:4]=[C;H0;D2;+0:5]=[O;D1;H0:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:4]-[C:2](-[C;D1;H3:1])-[C;D1;H3:3] | 76.4 | [{"value": 76.4, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNC(=O)NC(C)C)COCC)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | A solution of 1-(4-aminobutyl)-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 5.1 mmol) in chloroform (36 mL) was cooled to 0° C., and a cold solution of isopropyl isocyanate (0.50 mL, 5.4 mmol) in chloroform (4 mL) was added slowly. A precipitate formed, and the reaction was stirred for 45 minutes. ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccc2c(c1)ncc1[nH]cnc12 | null | C(Cl)(Cl)Cl | null | 0.75 | CC(C)N=C=O.CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN>C(Cl)(Cl)Cl>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)NC(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-99bd2886c8094accacefd852ba8f9685 | CC(C)C(=O)Cl.CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCNCC1>>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCN(C(=O)CC(C)C)CC1 | C(C)(=O)OCC.Cl.Cl.BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC3CCNCC3)COCC.C(C)N(CC)CC.C(C(C)C)(=O)Cl>>BrC=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC3CCN(CC3)C(=O)CC(C)C)COCC | Cl[C:27](=[O:26])[CH:28]([CH3:29])[CH3:30].[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]3[c:18]2[n:19]1[CH2:20][CH:21]1[CH2:22][CH2:23][NH:24][CH2:31][CH2:32]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]([Br:14])... | CC(C)C(=O)Cl.CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCNCC1 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCN(C(=O)CC(C)C)CC1 | null | null | C(Cl)(Cl)Cl | Acylation | OtherReaction | aaa7c80569e6aa145ac8d7318e06893ee71aff0c965e85eca836522c948938d5 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc2c(c1)ncc1ncn(CC3CCNCC3)c12 | Cl-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C;D1;H3:4])-[C;D1;H3:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C:11](=[O;H0;D1;+0:2])-[CH2;D2;+0:1]-[C:3](-[C;D1;H3:4])-[C;D1;H3:5])-[C:9]-[C:10] | null | [] | null | null | 1 | HOUR | A solution of 7-bromo-2-ethoxymethyl-1-(piperidin-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine dihydrochloride (4.0 g, 8.1 mmol) and triethylamine (5.67 mL, 40.7 mmol) in chloroform (300 mL) was treated with isobutyryl chloride (0.85 mL, 8.1 mmol) according to the method described in Part A of Examples 583–611. The re... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2c(c1)ncc1[nH]cnc12.C1CC[NH]CC1 | null | C(Cl)(Cl)Cl | null | 1 | CC(C)C(=O)Cl.CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCNCC1>C(Cl)(Cl)Cl>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC1CCN(C(=O)CC(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc51e2ec186444cea2088f7c0632f2df | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN.O=C(Cl)C1CCCC1>>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)C1CCCC1 | C1(CCCC1)C(=O)Cl.C1(CCCC1)C(=O)Cl.NCCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)COCC.C(C)N(CC)CC>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNC(=O)C2CCCC2)COCC)Br | [CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]([Br:14])[cH:15][cH:16][c:17]3[c:18]2[n:19]1[CH2:20][CH2:21][CH2:22][CH2:23][NH2:24].Cl[C:25](=[O:26])[CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[n:6][c:7]2[c:8]([NH2:9])[n:10][c:11]3[cH:12][c:13]([Br:14])... | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN.O=C(Cl)C1CCCC1 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)C1CCCC1 | null | null | C(Cl)(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCCn1cnc2cnc3ccccc3c21)C1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5] | 64.2 | [{"value": 64.2, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNC(=O)C2CCCC2)COCC)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | Cyclopentanecarbonyl chloride (0.80 mL, 6.6 mmol) was added dropwise over a period of five minutes to a suspension of 1-(4-aminobutyl)-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine (2.00 g, 5.1 mmol) and triethylamine (0.78 mL, 5.6 mmol) in chloroform (200 mL). The reaction was stirred for 2.5 hours and then... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1ccc2c(c1)ncc1[nH]cnc12.C1CCCC1 | HCl | C(Cl)(Cl)Cl | null | 2.5 | CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN.O=C(Cl)C1CCCC1>C(Cl)(Cl)Cl>CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNC(=O)C1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a6d64d1788c245cd93ee5ac0dfe8896d | CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN.CS(=O)(=O)Cl>>CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNS(C)(=O)=O | NCCCCN1C(=NC=2C(=NC=3C=C(C=CC3C21)Br)N)CCC.C(C)N(CC)CC.CS(=O)(=O)Cl.C(C)N(CC)CC.CS(=O)(=O)Cl>>NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNS(=O)(=O)C)CCC)Br | [CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[c:7]([NH2:8])[n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[CH2:19][CH2:20][CH2:21][CH2:22][NH2:23].Cl[S:24]([CH3:25])(=[O:26])=[O:27]>>[CH3:1][CH2:2][CH2:3][c:4]1[n:5][c:6]2[c:7]([NH2:8])[n:9][c:10]3[cH:11][c:12]([Br:13])[cH:14][cH:15][c:16]3[c:17]2[n:18]1[... | CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN.CS(=O)(=O)Cl | CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNS(C)(=O)=O | null | null | C(Cl)(Cl)Cl | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccc2c(c1)ncc1nc[nH]c12 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 37.4 | [{"value": 37.4, "product": "NC1=NC=2C=C(C=CC2C2=C1N=C(N2CCCCNS(=O)(=O)C)CCC)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A suspension of 1-(4-aminobutyl)-7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (3.27 g, 8.7 mmol) and triethylamine (3.82 mL, 11.3 mmol) in chloroform (165 mL) was cooled to 0° C. A cold solution of methanesulfonyl chloride (1.37 mL, 9.6 mmol) in chloroform (10 mL) was slowly added. The reaction was allowed to war... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2c(c1)ncc1[nH]cnc12 | HCl | C(Cl)(Cl)Cl | 0 | null | CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCN.CS(=O)(=O)Cl>C(Cl)(Cl)Cl>CCCc1nc2c(N)nc3cc(Br)ccc3c2n1CCCCNS(C)(=O)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dda085bf850b4d2b8343c992ca684d49 | CC(C)(C)OC(=O)NCc1cccc(B(O)O)c1.CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)(C)O>>CCOCc1nc2c(N)nc3cc(-c4cccc(CNC(=O)OC(C)(C)C)c4)ccc3c2n1CC(C)(C)O | NC1=NC=2C=C(C=CC2C2=C1N=C(N2CC(C)(O)C)COCC)Br.C(C)(C)(C)OC(=O)NCC=1C=C(C=CC1)B(O)O>>C(C)(C)(C)OC(NCC1=CC(=CC=C1)C=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC(C)(C)O)COCC)=O | OB(O)[c:14]1[cH:15][cH:16][cH:17][c:18]([CH2:19][NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[cH:28]1.Br[c:13]1[cH:12][c:11]2[n:10][c:8]([NH2:9])[c:7]3[n:6][c:5]([CH2:4][O:3][CH2:2][CH3:1])[n:33]([CH2:34][C:35]([CH3:36])([CH3:37])[OH:38])[c:32]3[c:31]2[cH:30][cH:29]1>>[CH3:1][CH2:2][O:3][CH2:4][c:5]1[... | CC(C)(C)OC(=O)NCc1cccc(B(O)O)c1.CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)(C)O | CCOCc1nc2c(N)nc3cc(-c4cccc(CNC(=O)OC(C)(C)C)c4)ccc3c2n1CC(C)(C)O | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | 89ee2e97ba79660eddf3dfa788334e60a83082a3d4afa6ed050c5f1f85789150 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccc3c(c2)ncc2nc[nH]c23)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[c:10]:2:[c:11]:[c:12]:1.O-B(-O)-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[#7;a:9]:[c:8]1:[c:10]2:[c:11]:[c:12]:[c;H0;D3;+0:1](-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]):[c:2]:[c:3]:2:[#7;a:4]:[c:5]:[c:6]:1:[#7;a:7] | 84.8 | [{"value": 84.8, "product": "C(C)(C)(C)OC(NCC1=CC(=CC=C1)C=1C=CC=2C3=C(C(=NC2C1)N)N=C(N3CC(C)(C)O)COCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 1-(4-Amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol (2.62 g, 6.67 mmol) and 3-(N-tert-butoxycarbonylaminomethyl)phenylboronic acid (2.0 g, 8.0 mmol) were coupled according to the procedure described in Part J of Example 1. Palladium (II) acetate was added as a 5 mg/mL solution in tolue... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccc2c(c1)ncc1[nH]cnc12 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | c1ccc2c(c1)ncc1[nH]cnc12.c1ccccc1 | HBr.B | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C | null | null | CC(C)(C)OC(=O)NCc1cccc(B(O)O)c1.CCOCc1nc2c(N)nc3cc(Br)ccc3c2n1CC(C)(C)O>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)C>CCOCc1nc2c(N)nc3cc(-c4cccc(CNC(=O)OC(C)(C)C)c4)ccc3c2n1CC(C)(C)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f858daf9b78340f8a6c06509c19a3d65 | C=CCCCCCC.CCCCCCCC[PH](=O)O>>CCCCCCCCP(=O)(O)CCCCCCCC | C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O.C(CCCCCCC)P(O)=O.C=CCCCCCC.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>C(CCCCCCC)P(O)(=O)CCCCCCCC | [CH2:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][PH:9](=[O:10])[OH:11]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][P:9](=[O:10])([OH:11])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19] | C=CCCCCCC.CCCCCCCC[PH](=O)O | CCCCCCCCP(=O)(O)CCCCCCCC | null | null | C(C)O | Miscellaneous | OtherReaction | 57a64b6b42d462fe8276aa79a48b5b98ebab75830adad1905b3795c71ea65b06 | b53d8f361e43dc967c3023dcafe218466acf623d0cf729a1557a2a80217926eb | null | [C:1]-[C:2]-[CH;D2;+0:3]=[CH2;D1;+0:4].[C:5]-[C:6]-[PH;D3;+0:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[P;H0;D4;+0:7](=[O;D1;H0:8])(-[O;D1;H1:9])-[C:6]-[C:5] | 48.4 | [{"value": 48.4, "product": "C(CCCCCCC)P(O)(=O)CCCCCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.8, "product": "C(CCCCCCC)P(O)(=O)CCCCCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred mixture of 46.5 g (0.261 mol) of n-octylphosphinic acid in 250 mL 95% ethanol, 1-octene (58.6 g, 0.5218 mol) was added followed by 9.042 g (0.026 mol) of 70% benzoyl peroxide. The resulting mixture was refluxed for 8 hs, and then another 6.758 g (0.0196 mol) of benzoyl peroxide was added and the reaction c... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | null | null | null | null | null | C(C)O | null | null | C=CCCCCCC.CCCCCCCC[PH](=O)O>C(C)O>CCCCCCCCP(=O)(O)CCCCCCCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2a9a67b66c664cd1a09355b567f720a0 | C=CCCCCCC.O=[PH2][O-]>>CCCCCCCC[PH](=O)O | OO.O.[PH2](=O)[O-].[Na+].C=CCCCCCC.OO>>C(CCCCCCC)P(O)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].[PH2:9](=[O:10])[O-:11]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][PH:9](=[O:10])[OH:11] | C=CCCCCCC.O=[PH2][O-] | CCCCCCCC[PH](=O)O | null | null | S(O)(O)(=O)=O.C(C)O | Miscellaneous | OtherReaction | 57a64b6b42d462fe8276aa79a48b5b98ebab75830adad1905b3795c71ea65b06 | b53d8f361e43dc967c3023dcafe218466acf623d0cf729a1557a2a80217926eb | null | [C:1]-[C:2]-[CH;D2;+0:3]=[CH2;D1;+0:4].[O-;H0;D1:5]-[PH2;D2;+0:6]=[O;D1;H0:7]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[PH;D3;+0:6](=[O;D1;H0:7])-[OH;D1;+0:5] | 84.8 | [{"value": 84.8, "product": "C(CCCCCCC)P(O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.8, "product": "C(CCCCCCC)P(O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 95.1 g (0.897 mol) of sodium hypophosphite hydrate in 600 mL 95% ethanol, 23.8 mL of concentrated sulfuric acid was added. 1-Octene (33.6 g, 0.299 mol) was added to the stirred mixture followed by 1.69 g (0.0149 mol) of 30% hydrogen peroxide. The resulting mixture was refluxed for 8 hs, and then another... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | null | null | null | null | null | S(O)(O)(=O)=O.C(C)O | null | null | C=CCCCCCC.O=[PH2][O-]>S(O)(O)(=O)=O.C(C)O>CCCCCCCC[PH](=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-238025faf88247d8961dfc9c207d64dc | C=CCCCC.O=[PH2][O-]>>CCCCCC[PH](=O)O | OO.O.[PH2](=O)[O-].[Na+].C=CCCCC.OO>>C(CCCCC)P(O)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[PH2:7](=[O:8])[O-:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][PH:7](=[O:8])[OH:9] | C=CCCCC.O=[PH2][O-] | CCCCCC[PH](=O)O | null | null | S(O)(O)(=O)=O.C(C)O | Miscellaneous | OtherReaction | 57a64b6b42d462fe8276aa79a48b5b98ebab75830adad1905b3795c71ea65b06 | b53d8f361e43dc967c3023dcafe218466acf623d0cf729a1557a2a80217926eb | null | [C:1]-[C:2]-[CH;D2;+0:3]=[CH2;D1;+0:4].[O-;H0;D1:5]-[PH2;D2;+0:6]=[O;D1;H0:7]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[PH;D3;+0:6](=[O;D1;H0:7])-[OH;D1;+0:5] | 82.4 | [{"value": 82.4, "product": "C(CCCCC)P(O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.1, "product": "C(CCCCC)P(O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 95.2 g (0.898 mol) of sodium hypophosphite hydrate in 600 mL 95% ethanol, 23.8 mL of concentrated sulfuric acid was added. 1-hexene (25.2 g, 0.30 mol) was added to the stirred mixture followed by 1.76 g (0.0155 mol) of 30% hydrogen peroxide. The resulting mixture was refluxed for 8 hs, and then another ... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | null | null | null | null | null | S(O)(O)(=O)=O.C(C)O | null | null | C=CCCCC.O=[PH2][O-]>S(O)(O)(=O)=O.C(C)O>CCCCCC[PH](=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3117c94e8c2e4eec9d869a0c62704a73 | Nc1ccc(I)cc1.O=CO>>O=CNc1ccc(I)cc1 | IC1=CC=C(N)C=C1.C(C)(=O)OC(C)=O.C(=O)O>>C1=CC(=CC=C1NC=O)I | [NH2:3][c:4]1[cH:5][cH:6][c:7]([I:8])[cH:9][cH:10]1.O[CH:2]=[O:1]>>[O:1]=[CH:2][NH:3][c:4]1[cH:5][cH:6][c:7]([I:8])[cH:9][cH:10]1 | Nc1ccc(I)cc1.O=CO | O=CNc1ccc(I)cc1 | null | null | C1CCOC1.O.C(C)(=O)OCC.C1(=CC=CC=C1)C | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[CH;D2;+0:1]=[O;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[NH;D2;+0:3]-[c:4](:[c:5]):[c:6] | 99 | [{"value": 98.0, "product": "C1=CC(=CC=C1NC=O)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.0, "product": "C1=CC(=CC=C1NC=O)I", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 4-iodoaniline (30.0 g, 137 mmol) in 100 mL THF and 100 mL toluene, a solution of acetic anhydride (16.0 g, 157 mmol) and formic acid (10.8 g, 235 mmol) was slowly added from an addition funnel under argon atmosphere. The reaction mixture temperature was maintained below 15° C. during the addition. Afte... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | C1CCOC1.O.C(C)(=O)OCC.C1(=CC=CC=C1)C | null | 8 | Nc1ccc(I)cc1.O=CO>C1CCOC1.O.C(C)(=O)OCC.C1(=CC=CC=C1)C>O=CNc1ccc(I)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-df37945b51904d399bb64ad4006d4aeb | Brc1ccccc1.CC1(C)CC(=O)OC1=O>>CC(C)(CC(=O)c1ccc(Br)cc1)C(=O)O | BrC1=CC=CC=C1.CC1(C(OC(C1)=O)=O)C.[Al]>>BrC1=CC=C(C=C1)C(CC(C(=O)O)(C)C)=O | [cH:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1.[CH3:1][C:2]1([CH3:3])[CH2:4][C:5](=[O:6])[O:16][C:14]1=[O:15]>>[CH3:1][C:2]([CH3:3])([CH2:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]1)[C:14](=[O:15])[OH:16] | Brc1ccccc1.CC1(C)CC(=O)OC1=O | CC(C)(CC(=O)c1ccc(Br)cc1)C(=O)O | null | null | ClC(C)Cl | C-C Coupling | OtherReaction | 95de0079bfd4d0e2b70eac1863ad8bac063c1a1557f674f5eb3c0cde67534555 | 4836357c99dfeeac9d5083fedc379181a858ae45ac77bd85eb46e7e1a9df36f0 | c1ccccc1 | [O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-1.[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:7])-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c;H0;D3;+0:10](:[c:9]:[c:8]):[c:11]:[c:12] | 63 | [{"value": 63.0, "product": "BrC1=CC=C(C=C1)C(CC(C(=O)O)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.6, "product": "BrC1=CC=C(C=C1)C(CC(C(=O)O)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a chilled solution (ice/water bath) of bromobenzene (7.71 g, 49.1 mmol) and 3,3-dimethyldihydro-2,5-furandione (5.99 g, 46.7 mmol) in dichloroethane (150 mL) was added aluminum trichworide (13.28 g, 99.58 mmol). The ice bath was removed and the reaction mixture was stirred at rt overnight. The mixture was again chil... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Carboxylic acid.Ketone | c1ccccc1.C1CCOC1 | c1ccccc1 | c1ccccc1 | null | ClC(C)Cl | null | 8 | Brc1ccccc1.CC1(C)CC(=O)OC1=O>ClC(C)Cl>CC(C)(CC(=O)c1ccc(Br)cc1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-23f3c547abd546cb9fb9967371831408 | CC(C)(CC(=O)c1ccc(Br)cc1)C(=O)O.COC(C)(C)OC>>COC(=O)C(C)(C)CC(=O)c1ccc(Br)cc1 | BrC1=CC=C(C=C1)C(CC(C(=O)O)(C)C)=O.COC(C)(C)OC.Cl>>BrC1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O | [OH:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1.COC(C)(C)O[CH3:1]>>[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]1 | CC(C)(CC(=O)c1ccc(Br)cc1)C(=O)O.COC(C)(C)OC | COC(=O)C(C)(C)CC(=O)c1ccc(Br)cc1 | null | null | CO.O1CCOCC1 | Heteroatom Alkylation and Arylation | O-methylation | 996ec4961b01515261a54c290b3ca2791e1cd44e68716f1a7d216a92013249dc | f1d0c21bce3f84df8e09e027f5fecc48c78a31aaf69561ba0dce25419b3c823e | c1ccccc1 | C-O-C(-C)(-C)-O-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 99 | [{"value": 99.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 22 | HOUR | To a solution of 4-(4-bromophenyl)-2,2-dimethyl-4-oxobutanoic acid (8.33 g, 29.2 mmol) and 2,2-dimethoxypropane (3.95 g, 37.9 mmol) in methanol (100 mL) was added 1 M HCl in dioxane (2.0 mL). The reaction mixture was stirred at 50° C. for 22 h. The mixture was concentrated under reduced pressure. Toluene (2×60 mL) was ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether | Ester | null | null | c1ccccc1 | HO- | CO.O1CCOCC1 | 50 | 22 | CC(C)(CC(=O)c1ccc(Br)cc1)C(=O)O.COC(C)(C)OC>CO.O1CCOCC1>COC(=O)C(C)(C)CC(=O)c1ccc(Br)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e6285f699f614666a2681ea062cf0d89 | COC(=O)C(C)(C)CC(=O)c1ccc(Br)cc1.O=CNc1ccc(I)cc1>>COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(NC=O)cc2)cc1 | C1=CC(=CC=C1NC=O)I.B1(OC(C(O1)(C)C)(C)C)B2OC(C(O2)(C)C)(C)C.C(C)(=O)[O-].[K+].BrC1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O.C([O-])([O-])=O.[Cs+].[Cs+]>>C(=O)NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O | Br[c:14]1[cH:13][cH:12][c:11]([C:9]([CH2:8][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:6])[CH3:7])=[O:10])[cH:25][cH:24]1.I[c:15]1[cH:16][cH:17][c:18]([NH:19][CH:20]=[O:21])[cH:22][cH:23]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([NH:19][CH... | COC(=O)C(C)(C)CC(=O)c1ccc(Br)cc1.O=CNc1ccc(I)cc1 | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(NC=O)cc2)cc1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-] | CN(C=O)C.O.C(C)(=O)OCC.CCCCCC | C-C Coupling | Negishi | c762f793fad28f910ecef7baabecb58fd3905901ac0af2c73542eba7e0faa33e | a7a4ce9a92e2f8a62d28956a69a5cc384426ab72416e87d68c6a3feb23c22d66 | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].I-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 68 | [{"value": 68.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a 2-L three-necked round-bottomed flask were charged 4-iodoformanilide (30.0 g, 121 mmol, 1.0 eq), bis(pinacolato)diboron (30.8 g, 121 mmol, 1.0 eq), palladium acetate (0.82 g, 3.6 mmol, 3 mol %), potassium acetate (35.70 g, 364.3 mmol), and 500 mL N,N-dimethylformamide. The mixture was degassed by gently bubbling a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | Br-.I- | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C=O)C.O.C(C)(=O)OCC.CCCCCC | 80 | null | COC(=O)C(C)(C)CC(=O)c1ccc(Br)cc1.O=CNc1ccc(I)cc1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].CN(C=O)C.O.C(C)(=O)OCC.CCCCCC>COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(NC=O)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-009a97990c0745b6937ef7f388424e8c | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(NC=O)cc2)cc1>>COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)cc2)cc1 | C(=O)NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O.Cl>>NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O | O=C[NH:19][c:18]1[cH:17][cH:16][c:15](-[c:14]2[cH:13][cH:12][c:11]([C:9]([CH2:8][C:5]([C:3]([O:2][CH3:1])=[O:4])([CH3:6])[CH3:7])=[O:10])[cH:23][cH:22]2)[cH:21][cH:20]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]([CH3:6])([CH3:7])[CH2:8][C:9](=[O:10])[c:11]1[cH:12][cH:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([NH2:19])[cH:20][cH:21]2... | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(NC=O)cc2)cc1 | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)cc2)cc1 | null | null | CO | Reduction | Reduction of primary amides to amines | 755df58c254dea764fdda078ffd678ec540bba057c83683be04c253f1270ac7b | 025f7cefe51e71668ad5d09fca32df168e9b538347403e4d5c1748073e538adc | c1ccc(-c2ccccc2)cc1 | O=C-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 95.4 | [{"value": 95.0, "product": "NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.4, "product": "NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OC)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a suspension of methyl 4-[4′-(formylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoate (2.40 g, 7.07 mmol) in 20 mL methanol, was added 7 mL concentrated hydrochloric acid at below rt. The reaction mixture was stirred at rt overnight. The mixture was concentrated under reduced pressure and saturated aqueous sodi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | CO | null | 8 | COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(NC=O)cc2)cc1>CO>COC(=O)C(C)(C)CC(=O)c1ccc(-c2ccc(N)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9ff66aac35af4237ad585c7ebc53e6dd | CCOC(=O)C(CCc1ccccc1)C(=O)OCC.O=C(CBr)c1ccc(Br)cc1>>CCOC(=O)C(CCc1ccccc1)(CC(=O)c1ccc(Br)cc1)C(=O)OCC | Cl.[H-].[Na+].BrCC(=O)C1=CC=C(C=C1)Br.C1(=CC=CC=C1)CCC(C(=O)OCC)C(=O)OCC>>BrC1=CC=C(C=C1)C(CC(C(=O)OCC)(C(=O)OCC)CCC1=CC=CC=C1)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[C:25](=[O:26])[O:27][CH2:28][CH3:29].Br[CH2:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([Br:22])[cH:23][cH:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)([CH2:15][C:1... | CCOC(=O)C(CCc1ccccc1)C(=O)OCC.O=C(CBr)c1ccc(Br)cc1 | CCOC(=O)C(CCc1ccccc1)(CC(=O)c1ccc(Br)cc1)C(=O)OCC | null | null | O1CCCC1 | C-C Coupling | OtherReaction | 4bb1433a83171a818741815ed1611f54dc47d930932c002b83e8524407ba2582 | d7a41d4d502746dc050b2738c9dd1b697535250fee467eca2d3c201fc4e0267b | O=C(CCCCc1ccccc1)c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[C:10]-[C:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D4;+0:9](-[C:10]-[C:11])(-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15] | 61 | [{"value": 61.0, "product": "BrC1=CC=C(C=C1)C(CC(C(=O)OCC)(C(=O)OCC)CCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.5, "product": "BrC1=CC=C(C=C1)C(CC(C(=O)OCC)(C(=O)OCC)CCC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 16 | HOUR | To a 500 mL 3-neck round-bottom flask equipped with an argon inlet and an addition funnel, was added sodium hydride (95%, 1.40 g, 58.3 mmol) followed by tetrahydrofuran (30 mL). The resulting suspension was then cooled to 0° C. and diethyl 2-(2-phenylethyl)malonate (14.0 g, 53.0 mmol) in tetrahydrofuran (20 mL) was add... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ester.Ester | Ketone.Ester.Ester | null | null | c1ccccc1.c1ccccc1 | HBr | O1CCCC1 | 0 | 16 | CCOC(=O)C(CCc1ccccc1)C(=O)OCC.O=C(CBr)c1ccc(Br)cc1>O1CCCC1>CCOC(=O)C(CCc1ccccc1)(CC(=O)c1ccc(Br)cc1)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8fb6d4a6537a45d7bc04373d65cf36ce | CCOC(=O)C(CCc1ccccc1)(CC(=O)c1ccc(Br)cc1)C(=O)OCC>>CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(Br)cc1 | BrC1=CC=C(C=C1)C(CC(C(=O)OCC)(C(=O)OCC)CCC1=CC=CC=C1)=O.[OH-].[Na+]>>BrC1=CC=C(C=C1)C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O | CCOC(=O)[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH2:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([Br:22])[cH:23][cH:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH2:15][C:16](=[O:17])[c:18]1[cH:19][cH:20... | CCOC(=O)C(CCc1ccccc1)(CC(=O)c1ccc(Br)cc1)C(=O)OCC | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(Br)cc1 | null | null | CC(=O)C.C(C)O | Reduction | OtherReaction | 33f176f6ce02426b2726e71e3c19f64673952a2b50dd48518b89a08efe25965b | b45711df98eaf2a3f54e3027da3f1b57580ab2f6d54e9ac2a56731961e64969a | O=C(CCCCc1ccccc1)c1ccccc1 | C-C-O-C(=O)-[C;H0;D4;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[c:5])(-[C:6]-[C:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[c:5])-[C:6]-[C:7] | 65 | [{"value": 65.0, "product": "BrC1=CC=C(C=C1)C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.9, "product": "BrC1=CC=C(C=C1)C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a solution of diethyl 2-[2-(4-bromophenyl)-2-oxoethyl]-2-(2-phenylethyl)malonate (7.89 g, 17.1 mmol) in acetone (18.5 mL) and ethanol (17.0 mL) was added 1 N aqueous sodium hydroxide solution (17.1 mL), and the resulting solution was heated at 50° C. for 3 h. Solvent was then removed under reduced pressure via rotar... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ester | null | null | c1ccccc1.c1ccccc1 | HO- | CC(=O)C.C(C)O | 50 | null | CCOC(=O)C(CCc1ccccc1)(CC(=O)c1ccc(Br)cc1)C(=O)OCC>CC(=O)C.C(C)O>CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(Br)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-401204b21f9244dfb803dad51a9352ec | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(Br)cc1.O=[N+]([O-])c1ccc(B(O)O)cc1>>CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1 | C1(=CC=CC=C1)C.C([O-])([O-])=O.[Na+].[Na+].BrC1=CC=C(C=C1)C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O.[N+](=O)([O-])C1=CC=C(C=C1)B(O)O>>[N+](=O)([O-])C1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O | Br[c:21]1[cH:20][cH:19][c:18]([C:16]([CH2:15][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)=[O:17])[cH:32][cH:31]1.OB(O)[c:22]1[cH:23][cH:24][c:25]([N+:26](=[O:27])[O-:28])[cH:29][cH:30]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12]... | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(Br)cc1.O=[N+]([O-])c1ccc(B(O)O)cc1 | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1 | null | null | O1CCOCC1 | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(CCCCc1ccccc1)c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 75.2 | [{"value": 75.0, "product": "[N+](=O)([O-])C1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.2, "product": "[N+](=O)([O-])C1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | Ethyl 4-(4-bromophenyl)-4-oxo-2-(2-phenylethyl)butanoate (4.32 g, 11.1 mmol) and 4-nitrophenylboronic acid (2.22, 13.3 mmol) was added to a dry flask under argon. Toluene (100 mL), dioxane (25 mL), saturated aqueous sodium carbonate (30 mL), and [1,1′-bis(diphenyl-phosphino)-ferrocene]dichloro palladium(II) (1:1 comple... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | HBr.B | O1CCOCC1 | 85 | null | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(Br)cc1.O=[N+]([O-])c1ccc(B(O)O)cc1>O1CCOCC1>CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a3f07a1b4c274a639afd3ac301a7a5b5 | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1>>CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc(N)cc2)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O.Cl>>NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O | O=[N+:26]([O-])[c:25]1[cH:24][cH:23][c:22](-[c:21]2[cH:20][cH:19][c:18]([C:16]([CH2:15][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)=[O:17])[cH:30][cH:29]2)[cH:28][cH:27]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1... | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1 | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc(N)cc2)cc1 | null | [Fe] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(CCCCc1ccccc1)c1ccc(-c2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 95.2 | [{"value": 95.0, "product": "NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.2, "product": "NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OCC)CCC1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of ethyl 4-(4′-nitro-1,1′-biphenyl-4-yl)-4-oxo-2-(2-phenylethyl)butanoate (5.35 g, 12.4 mmol) in 85% ethanol (160 mL) was added iron powder (6.94 g) followed by a 2 N aqueous solution of hydrochloric acid (6.2 mL). The resulting mixture was refluxed for 2.5 h, filtered through a pad of Celite®, and extrac... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | [Fe].C(C)O | null | null | CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1>[Fe].C(C)O>CCOC(=O)C(CCc1ccccc1)CC(=O)c1ccc(-c2ccc(N)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ee9c0b103ab042eea52701b076134912 | CC(C)=O.CCCC(CC(=O)c1ccc(Br)cc1)(C(=O)[O-])C(=O)[O-]>>CCCC(CC(=O)c1ccc(Br)cc1)C(=O)OCC | BrC1=CC=C(C=C1)C(CC(C(=O)[O-])(C(=O)[O-])CCC)=O.CC(=O)C.[OH-].[Na+]>>BrC1=CC=C(C=C1)C(CC(C(=O)OCC)CCC)=O | C[C:18](=[O:17])[CH3:19].O=C([O-])[C:4]([CH2:3][CH2:2][CH3:1])([CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1)[C:15]([O-])=[O:16]>>[CH3:1][CH2:2][CH2:3][CH:4]([CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1)[C:15](=[O:16])[O:17][CH2:18][CH3:19] | CC(C)=O.CCCC(CC(=O)c1ccc(Br)cc1)(C(=O)[O-])C(=O)[O-] | CCCC(CC(=O)c1ccc(Br)cc1)C(=O)OCC | null | null | C(C)O | Acylation | OtherReaction | ab932c02ad5f3de757fcd72006af4dfbbf5ed07dbd4c1d8e6c87cdb2a27d31ab | 30c2c127c5cd46c77c59e05296c08e25077e8f68ec886ea7c29a791fdf58b61a | c1ccccc1 | C-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;H0;D1;+0:3].O=C(-[O-])-[C;H0;D4;+0:4](-[C:5]-[C:6])(-[C:7]-[C:8](=[O;D1;H0:9])-[c:10])-[C;H0;D3;+0:11](-[O-])=[O;D1;H0:12]>>[C:6]-[C:5]-[CH;D3;+0:4](-[C:7]-[C:8](=[O;D1;H0:9])-[c:10])-[C;H0;D3;+0:11](=[O;D1;H0:12])-[O;H0;D2;+0:3]-[CH2;D2;+0:1]-[C;D1;H3:2] | 20 | [{"value": 20.0, "product": "BrC1=CC=C(C=C1)C(CC(C(=O)OCC)CCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 15 | MINUTE | To a 200 mL flask was added crude 2-[2-(4-bromophenyl)-2-oxoethyl]-2-propylmalonate (7.62 g, 19.2 mmol), acetone (21 mL), and ethanol (19 mL), followed by addition of 1 N aqueous sodium hydroxide solution (19.1 mL). The reaction mixture was heated to 55° C. for 3 h. The clear, orange-red reaction mixture was then conce... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ester | null | null | c1ccccc1 | Other | C(C)O | 55 | 0.25 | CC(C)=O.CCCC(CC(=O)c1ccc(Br)cc1)(C(=O)[O-])C(=O)[O-]>C(C)O>CCCC(CC(=O)c1ccc(Br)cc1)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a78d2dcb1e5548479df3ef45416b6e74 | CCCC(CC(=O)c1ccc(Br)cc1)C(=O)OCC.O=[N+]([O-])c1ccc(B(O)O)cc1>>CCCC(CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1)C(=O)OCC | C([O-])([O-])=O.[Na+].[Na+].BrC1=CC=C(C=C1)C(CC(C(=O)OCC)CCC)=O.[N+](=O)([O-])C1=CC=C(C=C1)B(O)O>>[N+](=O)([O-])C1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OCC)CCC)=O | Br[c:11]1[cH:10][cH:9][c:8]([C:6]([CH2:5][CH:4]([CH2:3][CH2:2][CH3:1])[C:23](=[O:24])[O:25][CH2:26][CH3:27])=[O:7])[cH:22][cH:21]1.OB(O)[c:12]1[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1>>[CH3:1][CH2:2][CH2:3][CH:4]([CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11](-[c:12]2[cH:13][cH:14][c:15]([N+:16](=[O:... | CCCC(CC(=O)c1ccc(Br)cc1)C(=O)OCC.O=[N+]([O-])c1ccc(B(O)O)cc1 | CCCC(CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1)C(=O)OCC | null | null | O1CCOCC1.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:8]:[c:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:9]:[c:10] | 48 | [{"value": 48.0, "product": "[N+](=O)([O-])C1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OCC)CCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 46.9, "product": "[N+](=O)([O-])C1=CC=C(C=C1)C1=CC=C(C=C1)C(CC(C(=O)OCC)CCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 15 | MINUTE | To a 150 mL 3-neck flask fitted with a reflux condenser was added ethyl 2-[2-(4-bromophenyl)-2-oxoethyl]pentanoate (1.33 g, 4.10 mmol) and 4-nitro phenyl boronic acid (0.81 g, 4.9 mmol), dissolved in toluene (37 mL) and dioxane (10 mL), followed by addition of saturated aqueous sodium carbonate (11 mL). A thin-gauge ne... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | O1CCOCC1.C1(=CC=CC=C1)C | 85 | 0.25 | CCCC(CC(=O)c1ccc(Br)cc1)C(=O)OCC.O=[N+]([O-])c1ccc(B(O)O)cc1>O1CCOCC1.C1(=CC=CC=C1)C>CCCC(CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1)C(=O)OCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4d6fa58708e84e73b1226055e2995034 | CCOC(=O)C(CCOC)(CC(=O)c1ccc(Br)cc1)C(=O)OCC>>CCOC(=O)C(CCOC)CC(=O)c1ccc(Br)cc1 | [OH-].[Na+].BrC1=CC=C(C=C1)C(CC(C(=O)OCC)(C(=O)OCC)CCOC)=O>>BrC1=CC=C(C=C1)C(CC(C(=O)OCC)CCOC)=O | CCOC(=O)[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH2:7][CH2:8][O:9][CH3:10])[CH2:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH2:8][O:9][CH3:10])[CH2:11][C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]1 | CCOC(=O)C(CCOC)(CC(=O)c1ccc(Br)cc1)C(=O)OCC | CCOC(=O)C(CCOC)CC(=O)c1ccc(Br)cc1 | null | null | CC(=O)C.C(C)O | Reduction | OtherReaction | 33f176f6ce02426b2726e71e3c19f64673952a2b50dd48518b89a08efe25965b | b45711df98eaf2a3f54e3027da3f1b57580ab2f6d54e9ac2a56731961e64969a | c1ccccc1 | C-C-O-C(=O)-[C;H0;D4;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[c:5])(-[C:6]-[C:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11]>>[C:11]-[#8:10]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:1](-[C:2]-[C:3](=[O;D1;H0:4])-[c:5])-[C:6]-[C:7] | 86 | [{"value": 86.0, "product": "BrC1=CC=C(C=C1)C(CC(C(=O)OCC)CCOC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.0, "product": "BrC1=CC=C(C=C1)C(CC(C(=O)OCC)CCOC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 55 | CELSIUS | 15 | MINUTE | To a 150 mL flask was added diethyl 2-[2-(4-bromophenyl)-2-oxoethyl]-2-(2-methoxyethyl)malonate (1.59 g, 3.59 mmol) dissolved in acetone (16 mL) and ethanol (16 mL), followed by addition of 1N aqueous sodium hydroxide solution (3.6 mL). The reaction mixture was then heated at 55° C. for 3 h. The reaction mixture was co... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ester | null | null | c1ccccc1 | HO- | CC(=O)C.C(C)O | 55 | 0.25 | CCOC(=O)C(CCOC)(CC(=O)c1ccc(Br)cc1)C(=O)OCC>CC(=O)C.C(C)O>CCOC(=O)C(CCOC)CC(=O)c1ccc(Br)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5dcca08f75f24c8a9f19bca88699582c | CCOC(=O)C(CCOC)CC(=O)c1ccc(Br)cc1.O=[N+]([O-])c1ccc(B(O)O)cc1>>CCOC(=O)C(CCOC)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1 | C([O-])([O-])=O.[Na+].[Na+].BrC1=CC=C(C=C1)C(CC(C(=O)OCC)CCOC)=O.[N+](=O)([O-])C1=CC=C(C=C1)B(O)O>>COCCC(C(=O)OCC)CC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)[N+](=O)[O-] | Br[c:17]1[cH:16][cH:15][c:14]([C:12]([CH2:11][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH2:8][O:9][CH3:10])=[O:13])[cH:28][cH:27]1.OB(O)[c:18]1[cH:19][cH:20][c:21]([N+:22](=[O:23])[O-:24])[cH:25][cH:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH2:8][O:9][CH3:10])[CH2:11][C:12](=[O:13])[c:14]1[cH:15][cH:1... | CCOC(=O)C(CCOC)CC(=O)c1ccc(Br)cc1.O=[N+]([O-])c1ccc(B(O)O)cc1 | CCOC(=O)C(CCOC)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1 | null | null | O1CCOCC1.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 88 | [{"value": 88.0, "product": "COCCC(C(=O)OCC)CC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.3, "product": "COCCC(C(=O)OCC)CC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 15 | MINUTE | To a 150 mL 3-neck flask fitted with a reflux condenser was added ethyl 4-(4-bromophenyl)-2-(2-methoxyethyl)-4-oxobutanoate (1.06 g, 3.09 mmol) and 4-nitro-phenyl boronic acid (0.62 g, 3.70 mmol) dissolved in toluene (30 mL) and dioxane (8.50 mL), followed by addition of saturated aqueous sodium carbonate solution (8.5... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HBr.B | O1CCOCC1.C1(=CC=CC=C1)C | 85 | 0.25 | CCOC(=O)C(CCOC)CC(=O)c1ccc(Br)cc1.O=[N+]([O-])c1ccc(B(O)O)cc1>O1CCOCC1.C1(=CC=CC=C1)C>CCOC(=O)C(CCOC)CC(=O)c1ccc(-c2ccc([N+](=O)[O-])cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b2b04ebbc53f4f219f2866ba91f72edb | COC(=O)C1(CC(=O)c2ccc(Br)cc2)CCCC1.O=[N+]([O-])c1ccc(B(O)O)cc1>>COC(=O)C1(CC(=O)c2ccc(-c3ccc([N+](=O)[O-])cc3)cc2)CCCC1 | C([O-])([O-])=O.[Na+].[Na+].BrC1=CC=C(C=C1)C(CC1(CCCC1)C(=O)OC)=O.[N+](=O)([O-])C1=CC=C(C=C1)B(O)O.C1(=CC=CC=C1)C>>[N+](=O)([O-])C1=CC=C(C=C1)C1=CC=C(C=C1)C(CC1(CCCC1)C(=O)OC)=O | Br[c:12]1[cH:11][cH:10][c:9]([C:7]([CH2:6][C:5]2([C:3]([O:2][CH3:1])=[O:4])[CH2:24][CH2:25][CH2:26][CH2:27]2)=[O:8])[cH:23][cH:22]1.OB(O)[c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([CH2:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([N+:17... | COC(=O)C1(CC(=O)c2ccc(Br)cc2)CCCC1.O=[N+]([O-])c1ccc(B(O)O)cc1 | COC(=O)C1(CC(=O)c2ccc(-c3ccc([N+](=O)[O-])cc3)cc2)CCCC1 | null | null | O1CCOCC1.C(C)(=O)OCC.[Cl-].[Na+] | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(CC1CCCC1)c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 96.8 | [{"value": 93.0, "product": "[N+](=O)([O-])C1=CC=C(C=C1)C1=CC=C(C=C1)C(CC1(CCCC1)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.8, "product": "[N+](=O)([O-])C1=CC=C(C=C1)C1=CC=C(C=C1)C(CC1(CCCC1)C(=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 15 | MINUTE | To a 150 mL 3-neck flask fitted with a reflux condenser was added methyl 1-[2-(4-bromophenyl)-2-oxoethyl]cyclopentanecarboxylate (1.58 g, 4.64 mmol), 4-nitro phenyl boronic acid (0.93 g, 5.6 mmol), toluene (45 mL), and dioxane (13 mL), followed by the addition of a saturated aqueous sodium carbonate solution (13 mL). T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.C1CCCC1 | HBr.B | O1CCOCC1.C(C)(=O)OCC.[Cl-].[Na+] | 85 | 0.25 | COC(=O)C1(CC(=O)c2ccc(Br)cc2)CCCC1.O=[N+]([O-])c1ccc(B(O)O)cc1>O1CCOCC1.C(C)(=O)OCC.[Cl-].[Na+]>COC(=O)C1(CC(=O)c2ccc(-c3ccc([N+](=O)[O-])cc3)cc2)CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e3ba7497cd344fb1b0003b2107debd6a | COS(=O)(=O)OC.O=C(O)C1CCOCC1>>COC(=O)C1CCOCC1 | O1CCC(CC1)C(=O)O.C([O-])([O-])=O.[K+].[K+].S(=O)(=O)(OC)OC>>O1CCC(CC1)C(=O)OC | COS(=O)(=O)O[CH3:1].[OH:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1 | COS(=O)(=O)OC.O=C(O)C1CCOCC1 | COC(=O)C1CCOCC1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Methylation of OH with DMS | 9474aa79a2adc7353c0c02444ca598a6f486ecdd7ed5edb9ae0645721ee50389 | badd4f82161bb0ee7acffd023ea4caae5d036bce7065c10ab0a06e83a6a6f119 | C1CCOCC1 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 99.3 | [{"value": 99.0, "product": "O1CCC(CC1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.3, "product": "O1CCC(CC1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Tetrahydro-2H-pyran-4-carboxylic acid (1.00 g, 7.68 mmol) was slowly added to a stirred suspension of anhydrous potassium carbonate (1.17 g, 8.45 mmol) in acetone (40 mL), followed by dimethyl sulfate (0.8 mL, 8.45 mmol). The mixture was stirred and heated for 3 h. The inorganic salts were then removed by filtration an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ester | null | null | C1CCOCC1 | HO- | CC(=O)C | null | null | COS(=O)(=O)OC.O=C(O)C1CCOCC1>CC(=O)C>COC(=O)C1CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d5977edb28e5424eb7a5537df973da53 | CC(C)(C)OC(=O)CBr.COC(=O)C1CCOCC1>>COC(=O)C1(CC(=O)OC(C)(C)C)CCOCC1 | BrCC(=O)OC(C)(C)C.C(CCC)[Li].C(C)(C)NC(C)C.O1CCC(CC1)C(=O)OC>>C(C)(C)(C)OC(CC1(CCOCC1)C(=O)OC)=O | Br[CH2:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13].[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([CH2:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1 | CC(C)(C)OC(=O)CBr.COC(=O)C1CCOCC1 | COC(=O)C1(CC(=O)OC(C)(C)C)CCOCC1 | null | null | O.O1CCCC1 | C-C Coupling | OtherReaction | f1ac808bca1710c7bfd2d73523f305c1160f7ea189fea2b67137f9fc598cd703 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | C1CCOCC1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8].[C;D1;H3:9]-[#8:10]-[C:11](=[O;D1;H0:12])-[CH;D3;+0:13]1-[C:14]-[C:15]-[#8:16]-[C:17]-[C:18]-1>>[C;D1;H3:6]-[C:5](-[C;D1;H3:7])(-[C;D1;H3:8])-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[C;H0;D4;+0:13]1(-[C:11](=[O;D1;H0:12])-[#8:10]... | 56.8 | [{"value": 56.0, "product": "C(C)(C)(C)OC(CC1(CCOCC1)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.8, "product": "C(C)(C)(C)OC(CC1(CCOCC1)C(=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -35 | CELSIUS | 1 | HOUR | Diisopropylamine (1.28 mL, 9.16 mmol) was diluted with tetrahydrofuran (2 mL) and cooled to −78° C. n-Butyllithium (2.5 M, 3.66 mL, 9.16 mmol) was added dropwise, and the solution was allowed to stir for 1 h. Methyl tetrahydro-2H-pyran-4-carboxylate (1.1 g, 7.63 mmol) was added as a solution in tetrahydrofuran (1.5 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | C1CCOCC1 | C1CCOCC1 | C1CCOCC1 | HBr | O.O1CCCC1 | -35 | 1 | CC(C)(C)OC(=O)CBr.COC(=O)C1CCOCC1>O.O1CCCC1>COC(=O)C1(CC(=O)OC(C)(C)C)CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-32f0b45fdb2849eb997c167048a03d3c | COC(=O)C1(CC(=O)OC(C)(C)C)CCOCC1>>COC(=O)C1(CC(=O)O)CCOCC1 | C(C)(C)(C)OC(CC1(CCOCC1)C(=O)OC)=O.FC(C(=O)O)(F)F>>COC(=O)C1(CCOCC1)CC(=O)O | CC(C)(C)[O:9][C:7]([CH2:6][C:5]1([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1)=[O:8]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([CH2:6][C:7](=[O:8])[OH:9])[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1 | COC(=O)C1(CC(=O)OC(C)(C)C)CCOCC1 | COC(=O)C1(CC(=O)O)CCOCC1 | null | null | ClCCl | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | C1CCOCC1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 104.5 | [{"value": 94.0, "product": "COC(=O)C1(CCOCC1)CC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 104.5, "product": "COC(=O)C1(CCOCC1)CC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To a solution of methyl 4-(2-tert-butoxy-2-oxoethyl)tetrahydro-2H-pyran-4-carboxylate (1.1 g, 4.26 mmol) in dichloromethane (5.0 mL) was added trifluoroacetic acid (5.0 mL) and the resulting solution was stirred at rt for 5 h. The mixture was concentrated under reduced pressure to afford [4-(methoxycarbonyl)tetrahydro-... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | C1CCOCC1 | Other | ClCCl | null | 5 | COC(=O)C1(CC(=O)OC(C)(C)C)CCOCC1>ClCCl>COC(=O)C1(CC(=O)O)CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2886457481ea407a9836e9cd75ae21a7 | Brc1ccccc1.COC(=O)C1(CC(=O)Cl)CCOCC1>>COC(=O)C1(CC(=O)c2ccc(Br)cc2)CCOCC1 | ClC(CC1(CCOCC1)C(=O)OC)=O.BrC1=CC=CC=C1.[Cl-].[Al+3].[Cl-].[Cl-]>>BrC1=CC=C(C=C1)C(CC1(CCOCC1)C(=O)OC)=O | [cH:9]1[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]1.Cl[C:7]([CH2:6][C:5]1([C:3]([O:2][CH3:1])=[O:4])[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1)=[O:8]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([CH2:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([Br:13])[cH:14][cH:15]2)[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1 | Brc1ccccc1.COC(=O)C1(CC(=O)Cl)CCOCC1 | COC(=O)C1(CC(=O)c2ccc(Br)cc2)CCOCC1 | null | null | ClCCl | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(CC1CCOCC1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7].[c:8]:[c:9]:[cH;D2;+0:10]:[c:11]:[c:12]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:10](:[c:9]:[c:8]):[c:11]:[c:12] | 55 | [{"value": 55.0, "product": "BrC1=CC=C(C=C1)C(CC1(CCOCC1)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.0, "product": "BrC1=CC=C(C=C1)C(CC1(CCOCC1)C(=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | To a solution of methyl 4-(2-chloro-2-oxoethyl)tetrahydro-2H-pyran-4-carboxylate (1.06 g, 4.8 mmol) and bromobenzene (1.13 g, 7.21 mmol) in dichloromethane (20 mL) at 0° C. was added aluminum chloride (1.92 g, 14.4 mmol). The ice-water bath was removed and the reaction mixture was stirred at rt for 16 h. The mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCOCC1 | HCl | ClCCl | null | 16 | Brc1ccccc1.COC(=O)C1(CC(=O)Cl)CCOCC1>ClCCl>COC(=O)C1(CC(=O)c2ccc(Br)cc2)CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-95ac54c9a77a48bb970bfef33b2bcba5 | COC(=O)C1(CC(=O)c2ccc(Br)cc2)CCOCC1.O=[N+]([O-])c1ccc(B(O)O)cc1>>COC(=O)C1(CC(=O)c2ccc(-c3ccc([N+](=O)[O-])cc3)cc2)CCOCC1 | BrC1=CC=C(C=C1)C(CC1(CCOCC1)C(=O)OC)=O.[N+](=O)([O-])C1=CC=C(C=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+].ClCCl>>[N+](=O)([O-])C1=CC=C(C=C1)C1=CC=C(C=C1)C(CC1(CCOCC1)C(=O)OC)=O | Br[c:12]1[cH:11][cH:10][c:9]([C:7]([CH2:6][C:5]2([C:3]([O:2][CH3:1])=[O:4])[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)=[O:8])[cH:23][cH:22]1.OB(O)[c:13]1[cH:14][cH:15][c:16]([N+:17](=[O:18])[O-:19])[cH:20][cH:21]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([CH2:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16](... | COC(=O)C1(CC(=O)c2ccc(Br)cc2)CCOCC1.O=[N+]([O-])c1ccc(B(O)O)cc1 | COC(=O)C1(CC(=O)c2ccc(-c3ccc([N+](=O)[O-])cc3)cc2)CCOCC1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | O.O1CCOCC1.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(CC1CCOCC1)c1ccc(-c2ccccc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | 79.3 | [{"value": 79.0, "product": "[N+](=O)([O-])C1=CC=C(C=C1)C1=CC=C(C=C1)C(CC1(CCOCC1)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.3, "product": "[N+](=O)([O-])C1=CC=C(C=C1)C1=CC=C(C=C1)C(CC1(CCOCC1)C(=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | Methyl 4-[2-(4-bromophenyl)-2-oxoethyl]tetrahydro-2H-pyran-4-carboxylate (820 mg, 2.40 mmol) and 4-nitrophenyl boronic acid (481 mg, 2.88 mmol) were combined in a dry flask under argon. Toluene (20 mL) and dioxane (5 mL) were added, and the resulting solution was degassed for 30 minutes by a flow of argon. The degassin... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1.C1CCOCC1 | HBr.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O.O1CCOCC1.C1(=CC=CC=C1)C | 85 | null | COC(=O)C1(CC(=O)c2ccc(Br)cc2)CCOCC1.O=[N+]([O-])c1ccc(B(O)O)cc1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].O.O1CCOCC1.C1(=CC=CC=C1)C>COC(=O)C1(CC(=O)c2ccc(-c3ccc([N+](=O)[O-])cc3)cc2)CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ffffb01d3bdd4e01bba1881b67a7067c | COC(=O)C1(CC(=O)c2ccc(-c3ccc([N+](=O)[O-])cc3)cc2)CCOCC1>>COC(=O)C1(CC(=O)c2ccc(-c3ccc(N)cc3)cc2)CCOCC1 | [N+](=O)([O-])C1=CC=C(C=C1)C1=CC=C(C=C1)C(CC1(CCOCC1)C(=O)OC)=O.Cl>>NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC1(CCOCC1)C(=O)OC)=O | O=[N+:17]([O-])[c:16]1[cH:15][cH:14][c:13](-[c:12]2[cH:11][cH:10][c:9]([C:7]([CH2:6][C:5]3([C:3]([O:2][CH3:1])=[O:4])[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)=[O:8])[cH:21][cH:20]2)[cH:19][cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([CH2:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([NH2:17])[cH:18... | COC(=O)C1(CC(=O)c2ccc(-c3ccc([N+](=O)[O-])cc3)cc2)CCOCC1 | COC(=O)C1(CC(=O)c2ccc(-c3ccc(N)cc3)cc2)CCOCC1 | null | [Fe] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(CC1CCOCC1)c1ccc(-c2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 91.4 | [{"value": 91.0, "product": "NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC1(CCOCC1)C(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.4, "product": "NC1=CC=C(C=C1)C1=CC=C(C=C1)C(CC1(CCOCC1)C(=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of methyl 4-[2-(4′-nitro-1,1′-biphenyl-4-yl)-2-oxoethyl]tetrahydro-2H-pyran-4-carboxylate (1.24 g, 3.25 mmol) in 85% ethanol (50 mL) was added iron powder (1.81 g), followed by 2 N aqueous HCl (1.62 mL), and the resulting mixture was refluxed for 2.5 h. The mixture was then filtered through a pad of Celit... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1.C1CCOCC1 | Other | [Fe].C(C)O | null | null | COC(=O)C1(CC(=O)c2ccc(-c3ccc([N+](=O)[O-])cc3)cc2)CCOCC1>[Fe].C(C)O>COC(=O)C1(CC(=O)c2ccc(-c3ccc(N)cc3)cc2)CCOCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c802f49817f42d6be8e2648cf3fa03e | COC(C)(C)OC.O=C(c1ccc(Br)cc1)[C@H]1CCCC[C@H]1C(=O)O>>COC(=O)[C@@H]1CCCC[C@@H]1C(=O)c1ccc(Br)cc1 | BrC1=CC=C(C(=O)[C@@H]2[C@@H](CCCC2)C(=O)O)C=C1.COC(C)(C)OC.Cl>>BrC1=CC=C(C(=O)[C@@H]2[C@@H](CCCC2)C(=O)OC)C=C1 | COC(C)(C)O[CH3:1].[OH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([Br:17])[cH:18][cH:19]1 | COC(C)(C)OC.O=C(c1ccc(Br)cc1)[C@H]1CCCC[C@H]1C(=O)O | COC(=O)[C@@H]1CCCC[C@@H]1C(=O)c1ccc(Br)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | O-methylation | 996ec4961b01515261a54c290b3ca2791e1cd44e68716f1a7d216a92013249dc | f1d0c21bce3f84df8e09e027f5fecc48c78a31aaf69561ba0dce25419b3c823e | O=C(c1ccccc1)C1CCCCC1 | C-O-C(-C)(-C)-O-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 42.1 | [{"value": 42.0, "product": "BrC1=CC=C(C(=O)[C@@H]2[C@@H](CCCC2)C(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.1, "product": "BrC1=CC=C(C(=O)[C@@H]2[C@@H](CCCC2)C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 3 | DAY | To a solution of cis-2-(4-bromobenzoyl)-1-cyclohexanecarboxylic acid (4.0 g, 12.85 mmol) in MeOH (50 mL) was added 2,2-dimethoxypropane (2.01 g, 19.28 mmol) and HCl (4.0 M in dioxane, 1.20 mL). The resulting solution was stirred at 40° C. for 3 days, and then evaporated to dryness. The resulting residue was purified by... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether | Ester | null | null | C1CCCCC1.c1ccccc1 | HO- | CO | 40 | 72 | COC(C)(C)OC.O=C(c1ccc(Br)cc1)[C@H]1CCCC[C@H]1C(=O)O>CO>COC(=O)[C@@H]1CCCC[C@@H]1C(=O)c1ccc(Br)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f28078c0604c469b887a017ec7139846 | COC(=O)[C@@H]1CCCC[C@@H]1C(=O)c1ccc(Br)cc1.Nc1ccc(B(O)O)cc1>>COC(=O)[C@@H]1CCCC[C@@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1 | C(=O)([O-])[O-].[Na+].[Na+].BrC1=CC=C(C(=O)[C@@H]2[C@@H](CCCC2)C(=O)OC)C=C1.NC1=CC=C(C=C1)B(O)O.ClCCl>>NC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)[C@@H]1[C@@H](CCCC1)C(=O)OC | Br[c:16]1[cH:15][cH:14][c:13]([C:11]([C@@H:10]2[C@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7][CH2:8][CH2:9]2)=[O:12])[cH:25][cH:24]1.OB(O)[c:17]1[cH:18][cH:19][c:20]([NH2:21])[cH:22][cH:23]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16](-[c:17]2[cH... | COC(=O)[C@@H]1CCCC[C@@H]1C(=O)c1ccc(Br)cc1.Nc1ccc(B(O)O)cc1 | COC(=O)[C@@H]1CCCC[C@@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1 | null | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2] | CCOC(=O)C.CCO.C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | d79a78c79f0c392f0911481acf5c300cc98205269acdb93c24fb610a61c4c868 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(c1ccc(-c2ccccc2)cc1)C1CCCCC1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-B(-O)-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9]:[c:10]):[c:4]:[c:5] | null | [] | 85 | CELSIUS | null | null | Methyl cis-2-(4-bromobenzoyl)cyclohexanecarboxylate (1.76 g, 5.41 mmol) and 4-amino phenyl boronic acid (1.13 g, 6.49 mmol) were added to a clean dry flask under argon. Toluene (50 mL), EtOH (20 mL), and 3 M aqueous Na2CO3 (14 mL, 43 mmol) were added, and resulting solution was degassed for 30 minutes by using a flow o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | C1CCCCC1.c1ccccc1.c1ccccc1 | HBr.B | C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].CCOC(=O)C.CCO.C1(=CC=CC=C1)C | 85 | null | COC(=O)[C@@H]1CCCC[C@@H]1C(=O)c1ccc(Br)cc1.Nc1ccc(B(O)O)cc1>C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P([C-]2C=CC=C2)C3=CC=CC=C3.Cl[Pd]Cl.[Fe+2].CCOC(=O)C.CCO.C1(=CC=CC=C1)C>COC(=O)[C@@H]1CCCC[C@@H]1C(=O)c1ccc(-c2ccc(N)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-91ac4de46f3e4b839aeb0ff63fe2cf3e | C[Si](C)(C)CCO.O=C(O)[C@@H]1CCCC[C@H]1C(=O)c1ccc(Br)cc1>>C[Si](C)(C)CCOC(=O)[C@@H]1CCCC[C@H]1C(=O)c1ccc(Br)cc1 | BrC1=CC=C(C(=O)[C@H]2[C@@H](CCCC2)C(=O)O)C=C1.C[Si](CCO)(C)C.CCN=C=NCCCN(C)C.O>>BrC1=CC=C(C(=O)[C@H]2[C@@H](CCCC2)C(=O)OCC[Si](C)(C)C)C=C1 | [CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][OH:7].O[C:8](=[O:9])[C@@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]1[C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([Br:22])[cH:23][cH:24]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[CH2:5][CH2:6][O:7][C:8](=[O:9])[C@@H:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]1[C:16](=[O:17])[c:18]... | C[Si](C)(C)CCO.O=C(O)[C@@H]1CCCC[C@H]1C(=O)c1ccc(Br)cc1 | C[Si](C)(C)CCOC(=O)[C@@H]1CCCC[C@H]1C(=O)c1ccc(Br)cc1 | null | null | C(Cl)Cl | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | O=C(c1ccccc1)C1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:10]-[C:9]-[C:8])-[C:5]-[C:6]=[O;D1;H0:7] | 37 | [{"value": 37.0, "product": "BrC1=CC=C(C(=O)[C@H]2[C@@H](CCCC2)C(=O)OCC[Si](C)(C)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.9, "product": "BrC1=CC=C(C(=O)[C@H]2[C@@H](CCCC2)C(=O)OCC[Si](C)(C)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | DAY | To a solution of trans-2-(4-bromobenzoyl)cyclohexanecarboxylic acid (5.0 g, 16.07 mmol) in DCM (80 mL) was added 2-(trimethylsilyl)ethanol (2.1 g, 17.68 mmol), N,N′-dimethylamino-pyridine (98 mg, 0.80 mmol), and EDCI (4.0 g, 20.89 mmol). The resulting reaction mixture was stirred at rt for 2 days. Water was added, and ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | C1CCCCC1.c1ccccc1 | HO- | C(Cl)Cl | null | 48 | C[Si](C)(C)CCO.O=C(O)[C@@H]1CCCC[C@H]1C(=O)c1ccc(Br)cc1>C(Cl)Cl>C[Si](C)(C)CCOC(=O)[C@@H]1CCCC[C@H]1C(=O)c1ccc(Br)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4f34df0009af4ec5b9397ec1a5edea37 | Brc1ccccc1.O=C1OC(=O)C2CC12>>O=C(c1ccc(Br)cc1)[C@H]1C[C@H]1C(=O)O | BrC1=CC=CC=C1.[Al+3].[Cl-].[Cl-].[Cl-].Cl.C12C(OC(C2C1)=O)=O>>BrC1=CC=C(C(=O)[C@@H]2[C@@H](C2)C(=O)O)C=C1 | [cH:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1.[O:1]=[C:2]1[CH:10]2[CH2:11][CH:12]2[C:13](=[O:14])[O:15]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1)[C@H:10]1[CH2:11][C@H:12]1[C:13](=[O:14])[OH:15] | Brc1ccccc1.O=C1OC(=O)C2CC12 | O=C(c1ccc(Br)cc1)[C@H]1C[C@H]1C(=O)O | null | null | C(Cl)Cl | C-C Coupling | OtherReaction | 36efb843272085513718adf2456d27080e06914a2cf60547cbc37c7344b11e9f | 4836357c99dfeeac9d5083fedc379181a858ae45ac77bd85eb46e7e1a9df36f0 | O=C(c1ccccc1)C1CC1 | [O;D1;H0:1]=[C:2]1-[O;H0;D2;+0:3]-[C;H0;D3;+0:4](=[O;D1;H0:5])-[CH;D3;+0:6]2-[C:7]-[CH;D3;+0:8]-1-2.[c:9]:[c:10]:[cH;D2;+0:11]:[c:12]:[c:13]>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:3])-[C@@H;D3;+0:8]1-[C:7]-[C@@H;D3;+0:6]-1-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c;H0;D3;+0:11](:[c:10]:[c:9]):[c:12]:[c:13] | 74.6 | [{"value": 65.0, "product": "BrC1=CC=C(C(=O)[C@@H]2[C@@H](C2)C(=O)O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.6, "product": "BrC1=CC=C(C(=O)[C@@H]2[C@@H](C2)C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a cold (0° C.) stirred solution of bromobenzene (9.09 g, 57.89 mmol) and AlCl3 (18.36 g, 137.84 mmol) in dry DCM (150 mL) was added 3-oxabicyclo[3.1.0]hexane-2,4-dione (5.40 g, 48.24 mmol). The reaction mixture was stirred at rt for 3 days. The dark-red solution was then poured into ice-cold water (120 mL), and conc... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride | Carboxylic acid.Ketone | c1ccccc1.C1OCC2CC12 | c1ccccc1 | c1ccccc1.C1CC1 | null | C(Cl)Cl | null | 72 | Brc1ccccc1.O=C1OC(=O)C2CC12>C(Cl)Cl>O=C(c1ccc(Br)cc1)[C@H]1C[C@H]1C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2fd5618e389a417881c57b535e63dc15 | COC(C)(C)OC.O=C(c1ccc(Br)cc1)[C@H]1C[C@H]1C(=O)O>>COC(=O)[C@@H]1C[C@@H]1C(=O)c1ccc(Br)cc1 | BrC1=CC=C(C(=O)[C@@H]2[C@@H](C2)C(=O)O)C=C1.COC(C)(C)OC.Cl>>BrC1=CC=C(C(=O)[C@@H]2[C@@H](C2)C(=O)OC)C=C1 | COC(C)(C)O[CH3:1].[OH:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@@H:7]1[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@@H:7]1[C:8](=[O:9])[c:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][cH:16]1 | COC(C)(C)OC.O=C(c1ccc(Br)cc1)[C@H]1C[C@H]1C(=O)O | COC(=O)[C@@H]1C[C@@H]1C(=O)c1ccc(Br)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | O-methylation | 996ec4961b01515261a54c290b3ca2791e1cd44e68716f1a7d216a92013249dc | f1d0c21bce3f84df8e09e027f5fecc48c78a31aaf69561ba0dce25419b3c823e | O=C(c1ccccc1)C1CC1 | C-O-C(-C)(-C)-O-[CH3;D1;+0:1].[C:2]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5]>>[C:2]-[C:3](=[O;D1;H0:4])-[O;H0;D2;+0:5]-[CH3;D1;+0:1] | 99.7 | [{"value": 99.0, "product": "BrC1=CC=C(C(=O)[C@@H]2[C@@H](C2)C(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "BrC1=CC=C(C(=O)[C@@H]2[C@@H](C2)C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 3 | DAY | To a solution of cis-2-(4-bromobenzoyl)cyclopropanecarboxylic acid (10.6 g, 36.63 mmol) in MeOH (250 mL) was added 2,2-dimethoxypropane (9.54 g, 91.59 mmol) and HCl (4.0 M in dioxane, 3.50 mL). The resulting solution was stirred at 40° C. for 3 days, and then evaporated to dryness. The resulting residue was purified by... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether | Ester | null | null | C1CC1.c1ccccc1 | HO- | CO | 40 | 72 | COC(C)(C)OC.O=C(c1ccc(Br)cc1)[C@H]1C[C@H]1C(=O)O>CO>COC(=O)[C@@H]1C[C@@H]1C(=O)c1ccc(Br)cc1 |
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