dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-28c886cb9ce14ef9a1ee1b4b0580332d | CC(=O)c1ccc(Br)cc1.SCCCS>>CC(c1ccc(Br)cc1)C1SCCCS1 | BrC1=CC=C(C=C1)C(C)=O.C(CCS)S.B(F)(F)F.CCOCC>>BrC1=CC=C(C=C1)C(C)C1SCCCS1 | O=[C:2]([CH3:1])[c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1.[SH:11][CH2:12][CH2:13][CH2:14][SH:15]>>[CH3:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([Br:7])[cH:8][cH:9]1)[CH:10]1[S:11][CH2:12][CH2:13][CH2:14][S:15]1 | CC(=O)c1ccc(Br)cc1.SCCCS | CC(c1ccc(Br)cc1)C1SCCCS1 | null | null | ClCCl.ClC(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 4758dc84fa113e6f0c3b6850de21934960e643c3350412341d86e1faa5438e76 | cca0c476bcede45e7917ec20f9c51c08f1c759c1b0a2d2c92077062e73c24406 | c1ccc(CC2SCCCS2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5].[SH;D1;+0:6]-[C:7]-[C:8]-[C:9]-[SH;D1;+0:10]>>[C;D1;H3:2]-[CH;D3;+0:1](-[C:11]1-[S;H0;D2;+0:6]-[C:7]-[C:8]-[C:9]-[S;H0;D2;+0:10]-1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | 48 | HOUR | To the compound p-bromoacetophenone (36.85 g, 0.185 mol) in trichloromethane (300 ml) was added 1,3-propanedithiol (25 g, 0.23 mol) and boron trifluoride etherate (3 ml). The resulting mixture was stirred at room temperature for 48 hours. The mixture was diluted with dichloromethane (500 ml), washed twice with 10% sodi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Aliphatic thiol.Aliphatic thiol | Monosulfide.Monosulfide | null | C1CSCSC1 | c1ccccc1.C1CSCSC1 | null | ClCCl.ClC(Cl)Cl | null | 48 | CC(=O)c1ccc(Br)cc1.SCCCS>ClCCl.ClC(Cl)Cl>CC(c1ccc(Br)cc1)C1SCCCS1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e1d06b03b61c4832b159fc423e9257f9 | BrCCCCBr.CC(c1ccc(Br)cc1)C1SCCCS1>>CC(c1ccc(CCCCBr)cc1)C1SCCCS1 | C(C)(=O)OCC.BrCCCCBr.BrC1=CC=C(C=C1)C(C)C1SCCCS1.C(C)(CC)[Li]>>BrCCCCC1=CC=C(C=C1)C(C)C1SCCCS1 | Br[CH2:7][CH2:8][CH2:9][CH2:10][Br:11].Br[c:6]1[cH:5][cH:4][c:3]([CH:2]([CH3:1])[CH:14]2[S:15][CH2:16][CH2:17][CH2:18][S:19]2)[cH:13][cH:12]1>>[CH3:1][CH:2]([c:3]1[cH:4][cH:5][c:6]([CH2:7][CH2:8][CH2:9][CH2:10][Br:11])[cH:12][cH:13]1)[CH:14]1[S:15][CH2:16][CH2:17][CH2:18][S:19]1 | BrCCCCBr.CC(c1ccc(Br)cc1)C1SCCCS1 | CC(c1ccc(CCCCBr)cc1)C1SCCCS1 | null | null | O1CCCC1 | C-C Coupling | Negishi | 530a9bd1eaaebd54d09786b6168a1d1d89df12b3fda60e0c00afadb98df85946 | 84e12b0159f1d183204538a38a0b22f090552039c6c4b4ca4a95700e436c4e5e | c1ccc(CC2SCCCS2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].Br-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8] | null | [] | null | null | 1.5 | HOUR | A solution of 4-bromo-1-(1,3-dithian-2-yl)ethylbenzene (27.2 g, 94 moles) in tetrahydrofuran (200 ml) was charged with sec-butyllithium (99 ml, 1.3M in cyclohexane, 0.13 mole) dropwise at −78° C. under nitrogen. The mixture was stirred at ambient temperature for 1.5 hours, and then quenched with 1,4-dibromobutane (4.2 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CSCSC1 | Br- | O1CCCC1 | null | 1.5 | BrCCCCBr.CC(c1ccc(Br)cc1)C1SCCCS1>O1CCCC1>CC(c1ccc(CCCCBr)cc1)C1SCCCS1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4913b0e304f84c2a81beefe32b706a4c | NO.O=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1>>ON=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1 | FC1=C(C=CC(=C1)F)C(=O)C1CN(CC1)CC1=CC=CC=C1.NO.Cl.C(C)(=O)[O-].[NH4+]>>FC1=C(C=CC(=C1)F)C(=NO)C1CN(CC1)CC1=CC=CC=C1 | [OH:1][NH2:2].O=[C:3]([c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]1[F:11])[CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH2:23]1>>[OH:1][N:2]=[C:3]([c:4]1[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]1[F:11])[CH:12]1[CH2:13][CH2:14][N:15]([CH2:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[CH... | NO.O=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1 | ON=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C(c1ccccc1)C1CCN(Cc2ccccc2)C1 | O=[C;H0;D3;+0:1](-[C:2](-[C:3])-[C:4]-[#7:5])-[c:6](:[c:7]):[c:8].[NH2;D1;+0:9]-[O;D1;H1:10]>>[#7:5]-[C:4]-[C:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:9]-[O;D1;H1:10])-[c:6](:[c:7]):[c:8])-[C:3] | 52 | [{"value": 52.0, "product": "FC1=C(C=CC(=C1)F)C(=NO)C1CN(CC1)CC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To the compound (2,4-difluorophenyl)[1-(phenylmethyl)-3-pyrrolidinyl]methanone (22 g) in 95% ethanol (350 ml) and water (100 ml) was added NH2OH.HCl (10.1 g) and ammonium acetate (12.7 g, 2.1 eq). The resulting mixture was refluxed for 3.5 hours. The mixture was then allowed to stir at room temperature for 24 hours. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccccc1.C1CC[NH]C1.c1ccccc1 | HO- | O.C(C)O | null | 24 | NO.O=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1>O.C(C)O>ON=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1c2866d7ff1e496ea78a346f834c26e9 | ON=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1>>Fc1ccc2c(C3CCN(Cc4ccccc4)C3)noc2c1 | FC1=C(C=CC(=C1)F)C(=NO)C1CN(CC1)CC1=CC=CC=C1.[OH-].[K+].O.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CN(CC2)CC2=CC=CC=C2)C=C1 | F[c:21]1[c:5]([C:6]([CH:7]2[CH2:8][CH2:9][N:10]([CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[CH2:18]2)=[N:19][OH:20])[cH:4][cH:3][c:2]([F:1])[cH:22]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][N:10]([CH2:11][c:12]4[cH:13][cH:14][cH:15][cH:16][cH:17]4)[CH2:18]3)[n:19][o:20][c:21]2[cH:22]1 | ON=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1 | Fc1ccc2c(C3CCN(Cc4ccccc4)C3)noc2c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | cfebb679a94a29342a57758c91b6c629149cdccb6d62df316a2e291ec25d681b | c3af886e80a4d8a4db0b9015a14ae7edf5d5d18deb2717f7ce3620ceac08ea61 | c1ccc(CN2CCC(c3noc4ccccc34)C2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;H0;D3;+0:5](=[N;H0;D2;+0:6]-[OH;D1;+0:7])-[C:8](-[C:9])-[C:10]-[#7:11]):[c:12]>>[#7:11]-[C:10]-[C:8](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[o;H0;D2;+0:7]:[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:1:[c:12])-[C:9] | 74.8 | [{"value": 74.8, "product": "C(\\C=C\\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CN(CC2)CC2=CC=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of (2,4-difluorophenyl)[1-(phenylmethyl)-3-pyrrolidinyl]methanone oxime (10.8 g, 34.2 mmoles), potassium hydroxide (10 g), water (100 ml), and ethanol (100 ml) was heated at reflux for 2 hr. At the end of the reaction, the solution was cooled and ethanol was removed on a rotary evaporator. The aqueous mixture... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Oxime | null | c1ccccc1 | c1ccc2oncc2c1 | C1CC[NH]C1.c1ccccc1.c1ccc2oncc2c1 | HF | C(C)O | null | null | ON=C(c1ccc(F)cc1F)C1CCN(Cc2ccccc2)C1>C(C)O>Fc1ccc2c(C3CCN(Cc4ccccc4)C3)noc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6b793585f62848809ec01c140b495935 | COc1cc(C=O)ccc1O.ClCCCBr>>COc1cc(C=O)ccc1OCCCCl | O.O=CC1=CC(OC)=C(O)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCCl>>ClCCCOC1=C(C=C(C=O)C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][cH:9][c:10]1[OH:11].Br[CH2:12][CH2:13][CH2:14][Cl:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][cH:9][c:10]1[O:11][CH2:12][CH2:13][CH2:14][Cl:15] | COc1cc(C=O)ccc1O.ClCCCBr | COc1cc(C=O)ccc1OCCCCl | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 37 | [{"value": 37.0, "product": "ClCCCOC1=C(C=C(C=O)C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 5.9, "product": "ClCCCOC1=C(C=C(C=O)C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of vanillin (30.4 g, 0.2 mol), K2CO3 (27.6 g) and acetone (150 ml) was stirred and refluxed for 0.5 hours. Heating was removed and 1-bromo-3-chloropropane (40.8 g, 0.26 mol) in acetone was added dropwise. The reaction was stirred and refluxed for 16 hours, and then it was poured into water. The aqueous mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | CC(=O)C | null | null | COc1cc(C=O)ccc1O.ClCCCBr>CC(=O)C>COc1cc(C=O)ccc1OCCCCl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-080ed4d2582e48539c815fdf98dc7577 | C=COC(=O)N1CCC(c2noc3cc(F)ccc23)C1>>Fc1ccc2c(C3CCNC3)noc2c1 | C(=C)OC(=O)N1CC(CC1)C1=NOC2=C1C=CC(=C2)F.Cl>>Cl.FC1=CC2=C(C(=NO2)C2CNCC2)C=C1 | C=COC(=O)[N:11]1[CH2:10][CH2:9][CH:8]([c:7]2[c:6]3[cH:5][cH:4][c:3]([F:2])[cH:16][c:15]3[o:14][n:13]2)[CH2:12]1>>[F:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([CH:8]3[CH2:9][CH2:10][NH:11][CH2:12]3)[n:13][o:14][c:15]2[cH:16]1 | C=COC(=O)N1CCC(c2noc3cc(F)ccc23)C1 | Fc1ccc2c(C3CCNC3)noc2c1 | null | null | C(C)(C)O | Reduction | Hydrogenolysis of tertiary amines | b8f95e8847b8644bde7f55684fbdd5ce4dd641748931e44ce5a651614b5011ea | 4693d071c7195c4d1d1e30a5794ffc365d4c1fab9edd2d709ddf2a18cef75754 | c1ccc2c(C3CCNC3)noc2c1 | C=C-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1>>[C:2]1-[C:3]-[C:4]-[C:5]-[NH;D2;+0:1]-1 | null | [] | 0 | CELSIUS | null | null | A mixture of 3-(6-fluoro-1,2-benzisoxazol-3-yl)-1-pyrrolidinylcarboxylic acid ethenyl ester (5.1 g, 18.4 mmol, hydrochloride acid (5 ml), and isopropyl alcohol (50 ml) was heated at reflux for 3.5 hr. At the end of the reaction, the solvent was reduced to about 30 ml on a rotary evaporator and the mixture was cooled to... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Vinyl | Secondary amine | C1CC[NH]C1 | C1CCNC1 | C1CCNC1.c1ccc2oncc2c1 | HO- | C(C)(C)O | 0 | null | C=COC(=O)N1CCC(c2noc3cc(F)ccc23)C1>C(C)(C)O>Fc1ccc2c(C3CCNC3)noc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-27cda37f683d45c0a64365778b1ece4b | BrCCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>>Fc1ccc2c(C3CCN(CCCCBr)CC3)noc2c1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCCCBr>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCCBr)C=C1 | Br[CH2:11][CH2:12][CH2:13][CH2:14][Br:15].[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][NH:10][CH2:16][CH2:17]3)[n:18][o:19][c:20]2[cH:21]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][CH2:14][Br:15])[CH2:16][CH2:17]3)[n:18][o:19][c:20]2[cH:21]1 | BrCCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1 | Fc1ccc2c(C3CCN(CCCCBr)CC3)noc2c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCNCC3)noc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | 8 | HOUR | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (12 in, 55 mmol), K2CO3 (13 m) and 1,4-dibromobutane (20 m, 9.3 mmol, 1.7 eq) in acetonitrile (300 ml) was stirred at room temperature overnight. The inorganic material was filtered. The solution was concentrated to ˜80 ml, when crystals crashed out. The product... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N | null | 8 | BrCCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N>Fc1ccc2c(C3CCN(CCCCBr)CC3)noc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-208e7a31260143b7baa9163c46186c76 | CC(=O)OCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>>CC(=O)OCCN1CCC(c2noc3cc(F)ccc23)CC1 | C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].C(C)(=O)OCCBr>>C(\C=C\C(=O)O)(=O)O.C(C)(=O)OCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F | Br[CH2:6][CH2:5][O:4][C:2]([CH3:1])=[O:3].[NH:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1 | CC(=O)OCCBr.Fc1ccc2c(C3CCNCC3)noc2c1 | CC(=O)OCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N.C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCNCC3)noc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6])-[C:10]-[C:11] | null | [] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.0 gm, 13.6 mmol), K2CO3 (3.5 m, 25 mmol), 2-bromoethyl acetate (4 gm, 26.5 mmol) in acetonitrile (50 ml) was heated at reflux for 4 hr. After cooling to room temperature, the inorganic salts were filtered and washed with DCM (dichloromethane 50 ml). The organ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N.C(C)O | null | null | CC(=O)OCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N.C(C)O>CC(=O)OCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7f0c453459844830a5dfe770f1ee7a44 | ClCCN1CCOCC1.Fc1ccc2c(C3CCNCC3)noc2c1>>Fc1ccc2c(C3CCN(CCN4CCOCC4)CC3)noc2c1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.Cl.ClCCN1CCOCC1.C(=O)([O-])[O-].[K+].[K+]>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2CCOCC2)C=C1 | Cl[CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1.[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][NH:10][CH2:19][CH2:20]3)[n:21][o:22][c:23]2[cH:24]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][N:13]4[CH2:14][CH2:15][O:16][CH2:17][CH2:18]4)[CH2:19][CH2:20]3)[... | ClCCN1CCOCC1.Fc1ccc2c(C3CCNCC3)noc2c1 | Fc1ccc2c(C3CCN(CCN4CCOCC4)CC3)noc2c1 | null | null | C(C)#N.C(Cl)Cl | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCN(CCN4CCOCC4)CC3)noc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.0 gm, 13.6 mmol), 2-chloroethyl morpholine hydrochloride (4.46 gm, 29.7 mmol) and K2CO3 (7.3 gm, 2.2 eq) in acetonitrile (60 ml) was heated at reflux for 24 hr. The crude mixture was diluted with DCM and filtered. The solvent was concentrated to an oil (˜7.1 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1COCC[NH]1.c1ccc2oncc2c1 | HCl | C(C)#N.C(Cl)Cl | null | null | ClCCN1CCOCC1.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N.C(Cl)Cl>Fc1ccc2c(C3CCN(CCN4CCOCC4)CC3)noc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a453c7ef0c45442b84a793728bfaaf18 | Fc1ccc2c(C3CCNCC3)noc2c1.O=C1NC(=O)c2c(CCBr)cccc21>>O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCCC1=C2C(C(=O)NC2=O)=CC=C1.C(C)#N>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C=3C(C2=O)=CC=CC3)=O)C=C1 | [NH:14]1[CH2:15][CH2:16][CH:17]([c:18]2[n:19][o:20][c:21]3[cH:22][c:23]([F:24])[cH:25][cH:26][c:27]23)[CH2:28][CH2:29]1.Br[CH2:12][CH2:13][c:4]1[c:3]2[c:8]([cH:7][cH:6][cH:5]1)[C:9](=[O:10])[NH:11][C:2]2=[O:1]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][... | Fc1ccc2c(C3CCNCC3)noc2c1.O=C1NC(=O)c2c(CCBr)cccc21 | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | caede2b65a541826d0816af10d43f7c550425032c949a27fc1d2af4936a75676 | 4f85b4d0af17555b490073b5bd8727ffab737e6008592e3cbb27e5b30c359ff1 | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3ccccc23)CC1 | Br-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]1:[c:7]-[C:8](=[O;D1;H0:9])-[NH;D2;+0:10]-[C:11]-1=[O;D1;H0:12].[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]>>[C:13]-[C:14]-[N;H0;D3;+0:15](-[CH2;D2;+0:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:11](=[O;D1;H0:12])-[c:6](:[c:7]-[C:8]-1=[O;D1;H0:9]):[cH;D2;+0:3]:[c:... | null | [] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (5 15 gm 23 4 mmol) K2CO3 (4.2 gm, 30.4 mmol) and 2-bromoethyl phthalimide (7.13 gm, 28 mmol) in acetonitrile (250 ml) was heated at reflux for 3.5 hr. The solids and solvent were removed. The residue was purified by flash chromatography (SiO2, 110 m, eluted wit... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Unsubstituted dicarboximide.Secondary amine | Substituted dicarboximide.Tertiary amine | C1CCNCC1.c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | null | null | null | Fc1ccc2c(C3CCNCC3)noc2c1.O=C1NC(=O)c2c(CCBr)cccc21>>O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5ab47f7791f64971b641945e6dcd0293 | COCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>>COCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].COCCBr.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.COCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F | Br[CH2:4][CH2:3][O:2][CH3:1].[NH:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][o:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1>>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([c:9]2[n:10][o:11][c:12]3[cH:13][c:14]([F:15])[cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1 | COCCBr.Fc1ccc2c(C3CCNCC3)noc2c1 | COCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N.C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCNCC3)noc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | null | [] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.75 gm, 17 mmol), K2CO3 (3 gm, 21.7 mmol), bromoethyl methyl ether (2.84 gm, 20.4 mmol) in acetonitrile (150 ml) was heated at reflux for 3.5 hr. The reaction was cooled. The inorganics were filtered and rinsed with DCM. The organic solution was concentrated d... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N.C(C)O | null | null | COCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N.C(C)O>COCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6eac25b428c242fcae169939f1e30c6f | CC(=O)OCCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>>CC(=O)OCCCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].C(C)(=O)OCCCCBr.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.C(C)(=O)OCCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F | Br[CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:2]([CH3:1])=[O:3].[NH:9]1[CH2:10][CH2:11][CH:12]([c:13]2[n:14][o:15][c:16]3[cH:17][c:18]([F:19])[cH:20][cH:21][c:22]23)[CH2:23][CH2:24]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][CH:12]([c:13]2[n:14][o:15][c:16]3[cH:17][c:18]([F:19])[cH:20][cH:21]... | CC(=O)OCCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1 | CC(=O)OCCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(C)#N.C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCNCC3)noc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7]-[C:8] | null | [] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (9.5 gm, 41 mmol), K2CO3 (7.2 m, 51 mmol), and 4-bromobutyl acetate (10 gm, 51 mmol) in acetonitrile (200 ml) was heated at reflux for 3½ hr. At the end of the reaction, the solution was cooled and filtered. The inorganic salt was washed with DCM (50 ml). The or... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | HBr | C(C)#N.C(C)O | null | null | CC(=O)OCCCCBr.Fc1ccc2c(C3CCNCC3)noc2c1>C(C)#N.C(C)O>CC(=O)OCCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c0f8749e22164827b4b11ae7a7ae291f | CCN(CC)CC.O=C(O)/C=C/C(=O)O.OCCCCN1CCC(c2noc3cc(F)ccc23)CC1>>CCCCCCCCCC(=O)OCCCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCCO)C=C1.C(C)N(CC)CC.C(Cl)Cl.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.C(CCCCCCCCC)(=O)OCCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F | N([CH2:2][CH3:1])([CH2:6][CH3:3])[CH2:8][CH3:9].[C:10](=[O:11])([OH:35])/[CH:36]=[CH:37]/[C:38](=[O:39])[OH:40].[OH:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][CH:20]([c:21]2[n:22][o:23][c:24]3[cH:25][c:26]([F:27])[cH:28][cH:29][c:30]23)[CH2:31][CH2:32]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]... | CCN(CC)CC.O=C(O)/C=C/C(=O)O.OCCCCN1CCC(c2noc3cc(F)ccc23)CC1 | CCCCCCCCCC(=O)OCCCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | null | null | C(C)O | C-C Coupling | OtherReaction | 751760910e5f360277c3f4d3befcb89bbe0e920df03a91877e36a8d024b51b87 | c343030799bb933f3375c7d72f59363fd1b700abfc69826f97b066628943b37c | c1ccc2c(C3CCNCC3)noc2c1 | [C;D1;H3:1]-[CH2;D2;+0:2]-N(-[CH2;D2;+0:3]-[CH3;D1;+0:4])-[CH2;D2;+0:5]-[CH3;D1;+0:6].[C:7]-[C:8]-[OH;D1;+0:9].[O;D1;H0:10]=[C;H0;D3;+0:11](-[OH;D1;+0:12])/[CH;D2;+0:13]=[C:14]/[C:15](=[O;D1;H0:16])-[O;D1;H1:17]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:11](=[O;D1;H0:10])-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[C:18]-[CH2;D2;+0:3]-... | null | [] | null | null | 1 | HOUR | To a solution of 4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]butanol (2.0 gm, 6.84 mmol), triethylamine (1.0 gm, 10 mmol) in DCM (70 ml) decanoyl chloride (1.7 gm, 8.9 mmol) was added dropwise at room temperature. The mixture was stirred for 1 hr., then was concentrated to a crude solid. The solid was extracted... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol.Tertiary amine | Carboxylic acid.Ester | null | null | C1CC[NH]CC1.c1ccc2oncc2c1 | null | C(C)O | null | 1 | CCN(CC)CC.O=C(O)/C=C/C(=O)O.OCCCCN1CCC(c2noc3cc(F)ccc23)CC1>C(C)O>CCCCCCCCCC(=O)OCCCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8a727adcde214391bd3c5969455176ae | CCCCCCCCCC(=O)Cl.OCCCN1CCC(c2noc3cc(F)ccc23)CC1>>CCCCCCCCCC(=O)OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCO)C=C1.C(CCCCCCCCC)(=O)Cl>>C(\C=C\C(=O)O)(=O)O.C(CCCCCCCCC)(=O)OCCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F | Cl[C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])=[O:11].[OH:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH:19]([c:20]2[n:21][o:22][c:23]3[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[O:12][CH2... | CCCCCCCCCC(=O)Cl.OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | CCCCCCCCCC(=O)OCCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(Cl)Cl.C(C)O | Acylation | Schotten-Baumann to ester | 6cefe709828c5bd4655f254e75d5dff9e8876e192e7dd47256c1bc0067bc5291 | d8a7643b81ed07a6f633aa99465180dfa0565e61ae25aef36338ebb9837c9cef | c1ccc2c(C3CCNCC3)noc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4] | null | [] | null | null | 20 | MINUTE | To a solution 3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propanol (1.81 gm, 6.5 mmol) triethylamine (0.9 gm, 9.0 mmol) in DCM (45 ml) was added decanoyl chloride (1.5 gm, 7.8 mmol) dropwise at room temperature. The mixture was stirred for 20 minutes, then concentrated down to a crude solid. The solid was extra... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary alcohol | Ester | null | null | C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | C(Cl)Cl.C(C)O | null | 0.333333 | CCCCCCCCCC(=O)Cl.OCCCN1CCC(c2noc3cc(F)ccc23)CC1>C(Cl)Cl.C(C)O>CCCCCCCCCC(=O)OCCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-44dfbbff125c48ba970c1659d05f896a | NN.O.O=C1NC(=O)c2c(CCN3CCC(c4noc5cc(F)ccc45)CC3)cccc21>>NCCN1CCC(c2noc3cc(F)ccc23)CC1.NCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC2=C3C(C(=O)NC3=O)=CC=C2)C=C1.O.NN.C(\C=C\C(=O)O)(=O)O.Cl>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN)C=C1.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN)C=C1 | [NH2:1][NH2:23].[OH2:29].O=[C:21]1[NH:20][C:36](=O)[c:30]2[c:27]1[c:26]([CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([c:8]3[n:9][o:10][c:11]4[cH:12][c:13]([F:14])[cH:15][cH:16][c:17]34)[CH2:18][CH2:19]1)[cH:37][cH:32][cH:31]2>>[NH2:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][CH:7]([c:8]2[n:9][o:10][c:11]3[cH:12][c:13]([F:14])[cH:... | NN.O.O=C1NC(=O)c2c(CCN3CCC(c4noc5cc(F)ccc45)CC3)cccc21 | NCCN1CCC(c2noc3cc(F)ccc23)CC1.NCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | O.CO.C(C)O | Aromatic Heterocycle Formation | OtherReaction | 06df55fe7c20d2715d727c9ec277605163a83d63b338374b860fa13df9ceedd9 | 5524a9ed289118e58677b024c9c4475283bf219d6776b1f22527577b82e343ea | c1ccc2c(C3CCNCC3)noc2c1.c1ccc2c(C3CCNCC3)noc2c1 | O=[C;H0;D3;+0:1]1-[NH;D2;+0:2]-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4]2:[c:5]:[cH;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[CH2;D2;+0:9]-[C:10]-[#7:11]):[c;H0;D3;+0:12]:2-1.[NH2;D1;+0:13]-[NH2;D1;+0:14].[OH2;D0;+0:15]>>[#7:11]-[C:10]-[CH2;D2;+0:9]-[NH2;D1;+0:13].[F;D1;H0:16]-[c;H0;D3;+0:6]1:[c:5]:[c;H0;D3;+0:4]2:[o;H0;D2;+0:15]... | null | [] | null | null | null | null | A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl phthalimide (4.6 in, 11.7 mmol) and hydrazine monohydrate (1.17 gm, 23.4 mmol) in methanol (50 ml) was heated at reflux overnight. At the end of the reaction, methanol was removed to leave a crude solid. This was stirred with water (150 ml) and acid... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Unsubstituted dicarboximide | Aromatic halide.Primary amine.Primary amine.Tertiary amine | c1ccc2c(c1)CNC2 | C1CC[NH]CC1.c1ccc2oncc2c1 | C1CC[NH]CC1.c1ccc2oncc2c1.C1CC[NH]CC1.c1ccc2oncc2c1 | null | O.CO.C(C)O | null | null | NN.O.O=C1NC(=O)c2c(CCN3CCC(c4noc5cc(F)ccc45)CC3)cccc21>O.CO.C(C)O>NCCN1CCC(c2noc3cc(F)ccc23)CC1.NCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f34710d665c9438d879b93c90a0182d6 | CC(=O)Cl.NCCN1CCC(c2noc3cc(F)ccc23)CC1>>NC(=O)CCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN)C=C1.C(C)N(CC)CC.C(\C=C\C(=O)O)(=O)O.C(C)(=O)Cl>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCC(=O)N)C=C1 | Cl[C:2](=[O:3])[CH3:4].[NH2:1][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1>>[NH2:1][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1 | CC(=O)Cl.NCCN1CCC(c2noc3cc(F)ccc23)CC1 | NC(=O)CCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(Cl)Cl.C(C)O | Acylation | OtherReaction | 74356bef414ba31a0485b52d7495e90a08f4a5b89d028b8ec303ccdb6ed5504f | 5d86061e72bfd6a9511ca0dd8b67e7f96dd93b070d7199a24f9e8328c94bd93b | c1ccc2c(C3CCNCC3)noc2c1 | Cl-[C;H0;D3;+0:1](-[CH3;D1;+0:2])=[O;D1;H0:3].[#7:4]-[C:5]-[CH2;D2;+0:6]-[NH2;D1;+0:7]>>[#7:4]-[C:5]-[CH2;D2;+0:6]-[CH2;D2;+0:2]-[C;H0;D3;+0:1](-[NH2;D1;+0:7])=[O;D1;H0:3] | null | [] | null | null | 4 | HOUR | A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.56 g, 9.7 mmol) and triethylamine (1.45 gm, 14.5 mmol) in DCM (50 ml) was treated with dropwise addition of acetyl chloride (1.0 gm, 12.7 mmol) at room temperature. The mixture was stirred for 4 hr at room temperature. The reaction mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Primary amide | null | null | C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | C(Cl)Cl.C(C)O | null | 4 | CC(=O)Cl.NCCN1CCC(c2noc3cc(F)ccc23)CC1>C(Cl)Cl.C(C)O>NC(=O)CCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e7e61fdfcdac4dda8221a474935e3d54 | COC(=O)Cl.NCCN1CCC(c2noc3cc(F)ccc23)CC1>>O=C(O)NCCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN)C=C1.C(C)N(CC)CC.C(\C=C\C(=O)O)(=O)O.ClC(=O)OC>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCNC(O)=O)C=C1 | C[O:11][C:10](Cl)=[O:9].[NH2:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][CH:18]([c:19]2[n:20][o:21][c:22]3[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1>>[O:9]=[C:10]([OH:11])[NH:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][CH:18]([c:19]2[n:20][o:21][c:22]3[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]23)[CH2:29... | COC(=O)Cl.NCCN1CCC(c2noc3cc(F)ccc23)CC1 | O=C(O)NCCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(Cl)Cl.C(C)O | Acylation | OtherReaction | 6c80fd18c280df460041be8a8c98767c9dba71f5f4f3f6ff808fe4bb8396e9cb | 2b67592a38ea6fc1c1963f5b8261965724e5e16c9a8cee8da26ed8100d66dfbc | c1ccc2c(C3CCNCC3)noc2c1 | C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](-Cl)=[O;D1;H0:3].[C:4]-[C:5]-[NH2;D1;+0:6]>>[C:4]-[C:5]-[NH;D2;+0:6]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 1 | HOUR | A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.0 gm, 7.6 mmol) and triethylamine (1.0 gm, 10 mmol) in DCM (50 ml) was treated with methyl chloroformate (860 mg, 9.12 mmol) dropwise at room temperature. The mixture was stirred for 1 hr. The reaction mixture was diluted with DCM and washed... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic acid | null | null | C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | C(Cl)Cl.C(C)O | null | 1 | COC(=O)Cl.NCCN1CCC(c2noc3cc(F)ccc23)CC1>C(Cl)Cl.C(C)O>O=C(O)NCCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f4bc8b7e39bb44548882008d588dd63a | ClCCCN1CCCCC1.Fc1ccc2c(C3CCNCC3)noc2c1.O.O=C([O-])[O-]>>Fc1ccc2c(C3CCN(CCCN4CCCCC4)CC3)noc2c1.O=C(O)/C=C/C(=O)O.O=C(O)/C=C/C(=O)O | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.Cl.ClCCCN1CCCCC1.C(=O)([O-])[O-].[K+].[K+].O>>C(\C=C\C(=O)O)(=O)O.C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCN2CCCCC2)C=C1 | Cl[CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1.[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][NH:10][CH2:20][CH2:21]3)[n:22][o:23][c:24]2[cH:25]1.[OH2:34].[O-:26][C:31](=[O:32])[O-:40]>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][N:14]4[C... | ClCCCN1CCCCC1.Fc1ccc2c(C3CCNCC3)noc2c1.O.O=C([O-])[O-] | Fc1ccc2c(C3CCN(CCCN4CCCCC4)CC3)noc2c1.O=C(O)/C=C/C(=O)O.O=C(O)/C=C/C(=O)O | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | C(C)#N | Acylation | OtherReaction | 5abf4ce96638af1fef71fa30c86fff983bcc6ae0a81b871495c8ad14ff13da86 | 1e44655a39628ea3cd903509b7d5e10cb6ac6bc1b1eb03e5733de839f4a001b9 | c1ccc2c(C3CCN(CCCN4CCCCC4)CC3)noc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8].[O-;H0;D1:9]-[C;H0;D3;+0:10](-[O-;H0;D1:11])=[O;D1;H0:12].[OH2;D0;+0:13]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8].[O;D1;H0:12]=[C;H0;D3;+0:10](-[O;D1;H1:14])/[C:15]=[C:16]/[C:17](-[O;D1;H1:18])=[O;H0;D1;+0:9].[O;D1;H1:19]-[C:20... | null | [] | null | null | null | null | A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (3.0 gm, 13.6 mmol), N-(3-chloropropyl)piperidine hydrochloride (4.05 gm, 20.4 mmol), K2CO3 (6 gm, 43.4 mmol), tetrabutyl-ammonium hydrogen sulfate (phase transfer catalyst, 2.3 gm) in acetonitrile (100 ml) and water (15 ml) was heated at reflux for 16 hr. The m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Carboxylic acid.Carboxylic acid.Carboxylic acid.Carboxylic acid.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CC[NH]CC1.c1ccc2oncc2c1 | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)#N | null | null | ClCCCN1CCCCC1.Fc1ccc2c(C3CCNCC3)noc2c1.O.O=C([O-])[O-]>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)#N>Fc1ccc2c(C3CCN(CCCN4CCCCC4)CC3)noc2c1.O=C(O)/C=C/C(=O)O.O=C(O)/C=C/C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5b098cfa176148babb9f4997ef60a01a | CN(C)CCCCl.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-]>>CN(C)CCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.Cl.CN(CCCCl)C.C(=O)([O-])[O-].[K+].[K+].C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.C(\C=C\C(=O)O)(=O)O.CN(CCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)C | Cl[CH2:6][CH2:5][CH2:4][N:2]([CH3:1])[CH3:3].[NH:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1.[O-:23][C:24]([O-:25])=[O:29]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH... | CN(C)CCCCl.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-] | CN(C)CCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | C(C)#N.O.C(C)O | Acylation | OtherReaction | 6e81dd2143b34ac8493b8c7a465af8abf3dc938c48f958db6f7d226ebb2c3120 | 5f494da60710a056b9f0e23ca9ed5ee350fb03b6598e6ff6e0034b17ff171889 | c1ccc2c(C3CCNCC3)noc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8].[O-;H0;D1:9]-[C;H0;D3;+0:10](-[O-;H0;D1:11])=[O;H0;D1;+0:12]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7]-[C:8].[O;D1;H1:13]-[C:14](=[O;H0;D1;+0:12])/[C:15]=[C:16]/[C;H0;D3;+0:10](=[O;H0;D1;+0:9])-[OH;D1;+0:11] | 56.9 | [{"value": 56.9, "product": "C(\\C=C\\C(=O)O)(=O)O.C(\\C=C\\C(=O)O)(=O)O.CN(CCCN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.05 gm, 13.8 mmol), 3-dimethylaminopropyl chloride hydrochloride (3.4 gm, 21 mmol), K2CO3 (6.2 gm 45 mmol), tetrabutylammonium hydrogen sulfate (phase transfer catalyst, 1.5 gm) in acetonitrile (100 ml) and water (50 ml) was heated at 60° C. overnight. The aqu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Carboxylic acid.Carboxylic acid.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)#N.O.C(C)O | 60 | null | CN(C)CCCCl.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-]>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)#N.O.C(C)O>CN(C)CCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d802e192d083454a9e2106c1e317bb29 | ClCCCOc1ccc2[nH]ccc2c1.Fc1ccc2c(C3CCNCC3)noc2c1>>Fc1ccc2c(C3CCN(CCCOc4ccc5[nH]ccc5c4)CC3)noc2c1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].ClCCCOC=1C=C2C=CNC2=CC1.CC#N>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC=2C=C3C=CNC3=CC2)C=C1 | Cl[CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]2[nH:19][cH:20][cH:21][c:22]2[cH:23]1.[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][NH:10][CH2:24][CH2:25]3)[n:26][o:27][c:28]2[cH:29]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][O:14][c:15]4[cH:16][cH:17... | ClCCCOc1ccc2[nH]ccc2c1.Fc1ccc2c(C3CCNCC3)noc2c1 | Fc1ccc2c(C3CCN(CCCOc4ccc5[nH]ccc5c4)CC3)noc2c1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc2c(C3CCN(CCCOc4ccc5[nH]ccc5c4)CC3)noc2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 123.4 | [{"value": 123.4, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC=2C=C3C=CNC3=CC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.6 g, 11.8 mmol), K2CO3 (1.6 g, 11.6 mmol), KI (200 mg), 5-(3-chloropropoxy)indole (2.2 g, 10.5 mmol) and CH3CN (100 ml) was stirred at reflux under N2 for 18 hours. The cooled reaction was poured into H2O and the aqueous mixture was extracted with EtOAc. The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.c1ccc2oncc2c1 | HCl | O | null | null | ClCCCOc1ccc2[nH]ccc2c1.Fc1ccc2c(C3CCNCC3)noc2c1>O>Fc1ccc2c(C3CCN(CCCOc4ccc5[nH]ccc5c4)CC3)noc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eebec035ef6e40b0b4a66840ba1b5bd7 | ClCCCOc1cccc2[nH]ccc12.Fc1ccc2c(C3CCNCC3)noc2c1>>Fc1ccc2c(C3CCN(CCCOc4cccc5[nH]ccc45)CC3)noc2c1 | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].ClCCCOC1=C2C=CNC2=CC=C1.CC#N.C(=O)([O-])[O-].[K+].[K+]>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C3C=CNC3=CC=C2)C=C1 | Cl[CH2:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18][c:19]2[nH:20][cH:21][cH:22][c:23]12.[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][NH:10][CH2:24][CH2:25]3)[n:26][o:27][c:28]2[cH:29]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([CH:7]3[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][O:14][c:15]4[cH:16][cH:17... | ClCCCOc1cccc2[nH]ccc12.Fc1ccc2c(C3CCNCC3)noc2c1 | Fc1ccc2c(C3CCN(CCCOc4cccc5[nH]ccc45)CC3)noc2c1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1cc(OCCCN2CCC(c3noc4ccccc34)CC2)c2cc[nH]c2c1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6](-[C:5]-[C:4])-[C:7]-[C:8] | 103.5 | [{"value": 103.5, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C3C=CNC3=CC=C2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 68 | HOUR | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (3.5 g, 16 mmol), K2CO3 (2.2 g, 16 mmol), KI (200 mg), 4-(3-chloropropoxy)indole (3.0 g, 14 mmol) and CH3CN (100 ml) was stirred at reflux under N2 for 7 hours and then at ambient temperature for 68 hours. Reflux was resumed for an additional 6 hours whereupon a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2[nH]ccc2c1.c1ccc2oncc2c1 | HCl | O | null | 68 | ClCCCOc1cccc2[nH]ccc12.Fc1ccc2c(C3CCNCC3)noc2c1>O>Fc1ccc2c(C3CCN(CCCOc4cccc5[nH]ccc45)CC3)noc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-15941cc2a1ba4b54bcc2e6719487eb85 | CC(=O)c1ccc(OCCCCl)c(O)c1.Fc1ccc2c(C3CCNCC3)nsc2c1>>CC(=O)c1ccc(OCCCN2CCC(c3nsc4cc(F)ccc34)CC2)c(O)c1 | FC1=CC2=C(C(=NS2)C2CCNCC2)C=C1.ClCCCOC1=C(C=C(C=C1)C(C)=O)O.C(=O)(O)[O-].[Na+].CC#N>>FC1=CC2=C(C(=NS2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=O)O)C=C1 | Cl[CH2:11][CH2:10][CH2:9][O:8][c:7]1[cH:6][cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:30][c:28]1[OH:29].[NH:12]1[CH2:13][CH2:14][CH:15]([c:16]2[n:17][s:18][c:19]3[cH:20][c:21]([F:22])[cH:23][cH:24][c:25]23)[CH2:26][CH2:27]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]... | CC(=O)c1ccc(OCCCCl)c(O)c1.Fc1ccc2c(C3CCNCC3)nsc2c1 | CC(=O)c1ccc(OCCCN2CCC(c3nsc4cc(F)ccc34)CC2)c(O)c1 | null | null | O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(OCCCN2CCC(c3nsc4ccccc34)CC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:7]-[C:8] | 97 | [{"value": 97.0, "product": "FC1=CC2=C(C(=NS2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisothiazole (2.4 g, 10.1 mmol), 1-[4-(3-chloropropoxy)-3-hydroxyphenyl]ethanone (2.5 g, 11.1 mmol), NaHCO3 (0.94 g, 11.1 mmol), KI (100 mg) and CH3CN (100 ml) was stirred at reflux under N2 for 65 hours. The cooled reaction was poured into H2O and the aqueous mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccc2sncc2c1 | HCl | O | null | null | CC(=O)c1ccc(OCCCCl)c(O)c1.Fc1ccc2c(C3CCNCC3)nsc2c1>O>CC(=O)c1ccc(OCCCN2CCC(c3nsc4cc(F)ccc34)CC2)c(O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cfcfc056b45c4e1180bae03eef4d47d8 | CS(=O)(=O)Cl.C[C@@H](CO)CN1CCC(c2noc3cc(F)ccc23)CC1>>C[C@@H](COS(C)(=O)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)C[C@H](CO)C)C=C1.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)OC[C@@H](CN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)C | Cl[S:5]([CH3:6])(=[O:7])=[O:8].[CH3:1][C@@H:2]([CH2:3][OH:4])[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([c:14]2[n:15][o:16][c:17]3[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]23)[CH2:24][CH2:25]1>>[CH3:1][C@@H:2]([CH2:3][O:4][S:5]([CH3:6])(=[O:7])=[O:8])[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([c:14]2[n:15][o:16][c:17]3[cH:18][c:1... | CS(=O)(=O)Cl.C[C@@H](CO)CN1CCC(c2noc3cc(F)ccc23)CC1 | C[C@@H](COS(C)(=O)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc2c(C3CCNCC3)noc2c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 1 | HOUR | To a mixture of (R)-(−)-3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-methyl-1-propanol (7.26 gm, 24.8 mmoles), triethylamine (3ml, 30 mmoles) in methylene chloride (DCM, 120 ml), methanesulfonyl chloride (3.13 gm, 27.3 moles) was added dropwise at 0° C. The mixture was stirred at room temperature for 1 hr., t... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | C(Cl)Cl | null | 1 | CS(=O)(=O)Cl.C[C@@H](CO)CN1CCC(c2noc3cc(F)ccc23)CC1>C(Cl)Cl>C[C@@H](COS(C)(=O)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d78e644e407743eda8c6368ad1321293 | CC(C)(CO)CBr.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-]>>CC(C)(CO)CN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1.C(=O)([O-])[O-].[K+].[K+].BrCC(CO)(C)C>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CC(CO)(C)C)C=C1 | Br[CH2:6][C:2]([CH3:1])([CH2:4][OH:5])[CH3:27].[NH:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1.[O-:23][C:28]([O-:25])=[O:29]>>[CH3:1][C:2]([CH3:3])([CH2:4][OH:5])[CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18]... | CC(C)(CO)CBr.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-] | CC(C)(CO)CN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | null | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC | O.C(C)#N | Acylation | OtherReaction | 6e81dd2143b34ac8493b8c7a465af8abf3dc938c48f958db6f7d226ebb2c3120 | 5f494da60710a056b9f0e23ca9ed5ee350fb03b6598e6ff6e0034b17ff171889 | c1ccc2c(C3CCNCC3)noc2c1 | Br-[CH2;D2;+0:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[CH3;D1;+0:4])-[C:5]-[O;D1;H1:6].[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11].[O-;H0;D1:12]-[C;H0;D3;+0:13](-[O-;H0;D1:14])=[O;D1;H0:15]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[C;H0;D4;+0:2](-[C;D1;H3:3])(-[C;D1;H3:16])-[C:5]-[O;D1;H1:6])-[C:10]-[C:11].[O;D1;H0:15]=[C;H0;D3;... | null | [] | null | null | null | null | A mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (3.0 gm, 13.6 mmoles), K2CO3 (12.5 gm, 17.5 mmoles), 3-bromo-2,2-dimethyl-1-propanol (3 gm, 21 mmoles, 1.5 eq.), tetrabutylammonium hydrogen sulfate (1 gm, phase transfer catalyst) in water (5 ml) and acetonitrile (150 ml) was heated at reflux for 43 days. TLC s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Carboxylic acid.Carboxylic acid.Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2oncc2c1 | Br- | S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.O.C(C)#N | null | null | CC(C)(CO)CBr.Fc1ccc2c(C3CCNCC3)noc2c1.O=C([O-])[O-]>S(=O)(=O)(O)[O-].C(CCC)[N+](CCCC)(CCCC)CCCC.O.C(C)#N>CC(C)(CO)CN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-aec7caf706e040a6bfae5c1b2f424356 | CS(=O)(=O)Cl.C[C@H](CO)CN1CCC(c2noc3cc(F)ccc23)CC1>>C[C@H](COS(C)(=O)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)C[C@@H](CO)C)C=C1.C(C)N(CC)CC.CS(=O)(=O)Cl>>CS(=O)(=O)OC[C@H](CN1CCC(CC1)C1=NOC2=C1C=CC(=C2)F)C | Cl[S:5]([CH3:6])(=[O:7])=[O:8].[CH3:1][C@H:2]([CH2:3][OH:4])[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([c:14]2[n:15][o:16][c:17]3[cH:18][c:19]([F:20])[cH:21][cH:22][c:23]23)[CH2:24][CH2:25]1>>[CH3:1][C@H:2]([CH2:3][O:4][S:5]([CH3:6])(=[O:7])=[O:8])[CH2:9][N:10]1[CH2:11][CH2:12][CH:13]([c:14]2[n:15][o:16][c:17]3[cH:18][c:19]... | CS(=O)(=O)Cl.C[C@H](CO)CN1CCC(c2noc3cc(F)ccc23)CC1 | C[C@H](COS(C)(=O)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | ClCCl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccc2c(C3CCNCC3)noc2c1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | 1 | HOUR | To a mixture of (S)-(+)-3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-methyl-1-propanol (8.8 gm, 30 mmoles), triethylamine (3.2 gm, 32 mmoles) in dichloromethane (DCM, 150 ml), methanesulfonyl chloride (4 gm, 35 mmoles) was added dropwise at 0° C. over 10 minutes. The mixture was stirred at room temperature fo... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | C1CC[NH]CC1.c1ccc2oncc2c1 | HCl | ClCCl | null | 1 | CS(=O)(=O)Cl.C[C@H](CO)CN1CCC(c2noc3cc(F)ccc23)CC1>ClCCl>C[C@H](COS(C)(=O)=O)CN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7a5a5ee8a3f740d1ac15cb2fc748681b | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)c2cc(Cl)c(Cl)cc21>>O=C1c2cc(Cl)c(Cl)cc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN)C=C1.ClC=1C=C2C(C(=O)OC2=O)=CC1Cl>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C=3C(C2=O)=CC(=C(C3)Cl)Cl)=O)C=C1 | [NH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH:19]([c:20]2[n:21][o:22][c:23]3[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1.O1[C:2](=[O:1])[c:3]2[cH:4][c:5]([Cl:6])[c:7]([Cl:8])[cH:9][c:10]2[C:11]1=[O:12]>>[O:1]=[C:2]1[c:3]2[cH:4][c:5]([Cl:6])[c:7]([Cl:8])[cH:9][c:10]2[C:11](=[O:12])[N:13]1[CH2:14][C... | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)c2cc(Cl)c(Cl)cc21 | O=C1c2cc(Cl)c(Cl)cc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | C(Cl)Cl | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3ccccc23)CC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[c:10](:[c:11]):[c:8](:[c:9])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | null | [] | null | null | 2 | HOUR | A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.83 gm, 10.7 mmol) and 4,5-dichlorophthalic anhydride (2.56 gm, 11.93 mmol, 1.1 eq) in methylene chloride (100 ml, DCM) was stirred for 2 h, white solids precipitated and the TLC showed disappearance of the starting material. The solvent was ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | C(Cl)Cl | null | 2 | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)c2cc(Cl)c(Cl)cc21>C(Cl)Cl>O=C1c2cc(Cl)c(Cl)cc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-53f8ae7ab9224b6e8cb83e5ed899aaa3 | Fc1ccc2c(C3CCNCC3)nsc2c1.O=C1c2ccccc2C(=O)N1CCBr>>O=C1c2ccccc2C(=O)N1CCN1CCC(c2nsc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NS2)C2CCNCC2)C=C1.C([O-])([O-])=O.[K+].[K+].BrCCN1C(C=2C(C1=O)=CC=CC2)=O>>FC1=CC2=C(C(=NS2)C2CCN(CC2)CCN2C(C=3C(C2=O)=CC=CC3)=O)C=C1 | [NH:14]1[CH2:15][CH2:16][CH:17]([c:18]2[n:19][s:20][c:21]3[cH:22][c:23]([F:24])[cH:25][cH:26][c:27]23)[CH2:28][CH2:29]1.Br[CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH... | Fc1ccc2c(C3CCNCC3)nsc2c1.O=C1c2ccccc2C(=O)N1CCBr | O=C1c2ccccc2C(=O)N1CCN1CCC(c2nsc3cc(F)ccc23)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1c2ccccc2C(=O)N1CCN1CCC(c2nsc3ccccc23)CC1 | Br-[CH2;D2;+0:1]-[C:2]-[#7:3](-[C:4]=[O;D1;H0:5])-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[C:2]-[#7:3](-[C:4]=[O;D1;H0:5])-[C:6]=[O;D1;H0:7])-[C:11]-[C:12] | null | [] | null | null | null | null | A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisothiazole (4.72 g, 0.02 mole), potassium carbonate (4.14 g, 0.03 mole) and N-(2-bromoethyl)phthalimide (6.35 g, 0.0025 mole) in 200 ml of acetonitrile is heated at reflux for 4 hours. The solids are then removed by filtration and the filtrate is concentrated und... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2sncc2c1 | HBr | C(C)#N | null | null | Fc1ccc2c(C3CCNCC3)nsc2c1.O=C1c2ccccc2C(=O)N1CCBr>C(C)#N>O=C1c2ccccc2C(=O)N1CCN1CCC(c2nsc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9aed2845cc6048e8a7650bf7674284d6 | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)c2c(Cl)ccc(Cl)c21>>O=C1c2c(Cl)ccc(Cl)c2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN)C=C1.ClC1=C2C(C(=O)OC2=O)=C(C=C1)Cl>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C=3C(C2=O)=C(C=CC3Cl)Cl)=O)C=C1 | [NH2:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH:19]([c:20]2[n:21][o:22][c:23]3[cH:24][c:25]([F:26])[cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1.O1[C:2](=[O:1])[c:3]2[c:4]([Cl:5])[cH:6][cH:7][c:8]([Cl:9])[c:10]2[C:11]1=[O:12]>>[O:1]=[C:2]1[c:3]2[c:4]([Cl:5])[cH:6][cH:7][c:8]([Cl:9])[c:10]2[C:11](=[O:12])[N:13]1[CH2:14][C... | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)c2c(Cl)ccc(Cl)c21 | O=C1c2c(Cl)ccc(Cl)c2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | ClCCl | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3ccccc23)CC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[c:10](:[c:11]):[c:8](:[c:9])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | null | [] | null | null | 1 | HOUR | A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.44 gm, 9.24 mmoles) and 3,6-dichlorophthalic anhydride (2.01 gm; 9.27 mmoles) in dichloromethane (DCM, 50 ml) was stirred at room temperature for 1 hr. White precipitates formed and the TLC of the reaction mixture showed that there was no st... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | ClCCl | null | 1 | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)c2c(Cl)ccc(Cl)c21>ClCCl>O=C1c2c(Cl)ccc(Cl)c2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3b0ed7012d3c4352aefc14fd34658495 | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)c2cc(Cl)ccc21>>O=C1c2ccc(Cl)cc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN)C=C1.ClC=1C=C2C(C(=O)OC2=O)=CC1>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C=3C(C2=O)=CC(=CC3)Cl)=O)C=C1 | [NH2:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][CH:18]([c:19]2[n:20][o:21][c:22]3[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1.O1[C:2](=[O:1])[c:3]2[cH:4][cH:5][c:6]([Cl:7])[cH:8][c:9]2[C:10]1=[O:11]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][c:6]([Cl:7])[cH:8][c:9]2[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][N:15]1[CH... | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)c2cc(Cl)ccc21 | O=C1c2ccc(Cl)cc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | ClCCl | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3ccccc23)CC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[c:10](:[c:11]):[c:8](:[c:9])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | null | [] | null | null | 3 | HOUR | A stirred mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.63 g, 0.01 mole) and 4-chlorophthalic anhydride (1.82 g, 0.01 mole) in dichloromethane (100 ml) is stirred at room temperature for 3 hours. The solvent is removed under reduced pressure and the residual material is purified by flash ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | ClCCl | null | 3 | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)c2cc(Cl)ccc21>ClCCl>O=C1c2ccc(Cl)cc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6e4a7b80558741188209f2cf0424ce21 | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)c1cccc(F)c1C(=O)O>>O=C1c2cccc(F)c2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN)C=C1.FC1=C(C(C(=O)O)=CC=C1)C(=O)O.C1(CCCCC1)N=C=NC1CCCCC1>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C=3C(C2=O)=C(C=CC3)F)=O)C=C1 | [NH2:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][CH:18]([c:19]2[n:20][o:21][c:22]3[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1.O[C:2](=[O:1])[c:3]1[cH:4][cH:5][cH:6][c:7]([F:8])[c:9]1[C:10](O)=[O:11]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][c:7]([F:8])[c:9]2[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][N:15]1[CH2... | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)c1cccc(F)c1C(=O)O | O=C1c2cccc(F)c2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | ClCCl | Acylation | OtherReaction | 03989296fe7fd00d3061010c1aadbbfb4b9eaa9ca91856790fffb1e1bf4b4c50 | b7eb222f11e89f2ccff57aab9a5106ae4173f0ba94ac518e1a9f3b22a378531d | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3ccccc23)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](-[C;H0;D3;+0:6](-O)=[O;D1;H0:7]):[c:8].[C:9]-[C:10]-[NH2;D1;+0:11]>>[C:9]-[C:10]-[N;H0;D3;+0:11]1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5](:[c:8])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | null | [] | null | null | 18 | HOUR | A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.37 gm, 8.98 mmoles), 3-fluorophthalic acid (1.82 in, 9.9 moles) and dicyclohexylcarbodiimide (DCC, 5.5 gm, 26.7 mmoles, 2.6 eq) in dichloromethane (DCM, 250 ml) was stirred at room temperature for 18 hrs. The solids were filtered off. The or... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Carboxylic acid.Primary amine | Substituted dicarboximide | null | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | ClCCl | null | 18 | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)c1cccc(F)c1C(=O)O>ClCCl>O=C1c2cccc(F)c2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7639107c90d449fe9f91df6fcf8fe0ee | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)c2cc(F)ccc21>>O=C1c2ccc(F)cc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN)C=C1.FC=1C=C2C(C(=O)OC2=O)=CC1>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C=3C(C2=O)=CC(=CC3)F)=O)C=C1 | [NH2:12][CH2:13][CH2:14][N:15]1[CH2:16][CH2:17][CH:18]([c:19]2[n:20][o:21][c:22]3[cH:23][c:24]([F:25])[cH:26][cH:27][c:28]23)[CH2:29][CH2:30]1.O1[C:2](=[O:1])[c:3]2[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]2[C:10]1=[O:11]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][c:6]([F:7])[cH:8][c:9]2[C:10](=[O:11])[N:12]1[CH2:13][CH2:14][N:15]1[CH2:... | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)c2cc(F)ccc21 | O=C1c2ccc(F)cc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | ClCCl | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3ccccc23)CC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[c:10](:[c:11]):[c:8](:[c:9])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | null | [] | null | null | 4 | HOUR | A stirred mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.63 g, 0.01 mole) and 4-fluorophthalic anhydride (1.83 g, 0.011 mole) in dichloromethane (100 ml) is stirred at room temperature for 4 hours. The solvent is then removed under reduced pressure and the residual solids are purified by f... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | ClCCl | null | 4 | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)c2cc(F)ccc21>ClCCl>O=C1c2ccc(F)cc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6b40f52e296841cf8e544064850b09d8 | Cc1ccc2c(c1)C(=O)OC2=O.NCCN1CCC(c2noc3cc(F)ccc23)CC1>>Cc1ccc2c(c1)C(=O)N(CCN1CCC(c3noc4cc(F)ccc34)CC1)C2=O | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN)C=C1.CC=1C=C2C(C(=O)OC2=O)=CC1.C1(CCCCC1)N=C=NC1CCCCC1>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C=3C(C2=O)=CC(=CC3)C)=O)C=C1 | O1[C:8](=[O:9])[c:6]2[c:5]([cH:4][cH:3][c:2]([CH3:1])[cH:7]2)[C:29]1=[O:30].[NH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH:16]([c:17]2[n:18][o:19][c:20]3[cH:21][c:22]([F:23])[cH:24][cH:25][c:26]23)[CH2:27][CH2:28]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[C:8](=[O:9])[N:10]([CH2:11][CH2:12][N:13]1[CH2:14][CH2... | Cc1ccc2c(c1)C(=O)OC2=O.NCCN1CCC(c2noc3cc(F)ccc23)CC1 | Cc1ccc2c(c1)C(=O)N(CCN1CCC(c3noc4cc(F)ccc34)CC1)C2=O | null | null | ClCCl | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3ccccc23)CC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[c:10](:[c:11]):[c:8](:[c:9])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | 17.7 | [{"value": 17.7, "product": "FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C=3C(C2=O)=CC(=CC3)C)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.44 gm, 9.24 mmoles), 4-methylphthalic anhydride (1.76 gm, 10.8 moles) and dicyclohexylcarbodiimide (2.1 gm, 1.0 moles) in dichloromethane (DCM, 100 ml) was stirred at room temperature for 2 hr. The insolubles were filtered off. The DCM solut... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | ClCCl | null | 2 | Cc1ccc2c(c1)C(=O)OC2=O.NCCN1CCC(c2noc3cc(F)ccc23)CC1>ClCCl>Cc1ccc2c(c1)C(=O)N(CCN1CCC(c3noc4cc(F)ccc34)CC1)C2=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2f53caabb6c3450d950e9dfb4b5e9cc7 | COc1ccc2c(c1)C(=O)OC2=O.NCCN1CCC(c2noc3cc(F)ccc23)CC1>>COc1ccc2c(c1)C(=O)N(CCN1CCC(c3noc4cc(F)ccc34)CC1)C2=O | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN)C=C1.COC=1C=C2C(C(=O)OC2=O)=CC1>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C=3C(C2=O)=CC(=CC3)OC)=O)C=C1 | O1[C:9](=[O:10])[c:7]2[c:6]([cH:5][cH:4][c:3]([O:2][CH3:1])[cH:8]2)[C:30]1=[O:31].[NH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH:17]([c:18]2[n:19][o:20][c:21]3[cH:22][c:23]([F:24])[cH:25][cH:26][c:27]23)[CH2:28][CH2:29]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[N:11]([CH2:12][CH2:13][N:14]1... | COc1ccc2c(c1)C(=O)OC2=O.NCCN1CCC(c2noc3cc(F)ccc23)CC1 | COc1ccc2c(c1)C(=O)N(CCN1CCC(c3noc4cc(F)ccc34)CC1)C2=O | null | null | ClCCl | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3ccccc23)CC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10](:[c:11])-[C;H0;D3;+0:5]-1=[O;D1;H0:4] | null | [] | null | null | 3 | HOUR | A stirred mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.63 g, 0.01 mole) and 4-methoxyphthalic anhydride (1.78 g, 0.01 mole) in dichloromethane (100 ml) is stirred at room temperature for 3 hours. The solvent is then removed under reduced pressure and the residual material is purified by ... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | ClCCl | null | 3 | COc1ccc2c(c1)C(=O)OC2=O.NCCN1CCC(c2noc3cc(F)ccc23)CC1>ClCCl>COc1ccc2c(c1)C(=O)N(CCN1CCC(c3noc4cc(F)ccc34)CC1)C2=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0b42a3522df94a06bdc0e5cfb8737820 | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)c2cc([N+](=O)[O-])ccc21>>O=C1c2ccc([N+](=O)[O-])cc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN)C=C1.[N+](=O)([O-])C=1C=C2C(C(=O)OC2=O)=CC1>>FC1=CC2=C(C(=NO2)C2CCN(CC2)CCN2C(C=3C(C2=O)=CC(=CC3)[N+](=O)[O-])=O)C=C1 | [NH2:14][CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][CH:20]([c:21]2[n:22][o:23][c:24]3[cH:25][c:26]([F:27])[cH:28][cH:29][c:30]23)[CH2:31][CH2:32]1.O1[C:2](=[O:1])[c:3]2[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]2[C:12]1=[O:13]>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][c:11]2[C:12](=[O:13])[... | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)c2cc([N+](=O)[O-])ccc21 | O=C1c2ccc([N+](=O)[O-])cc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 | null | null | ClCCl | Acylation | Phthalic anhydride to phthalimide | c3c986d6e09320348d40a4a59ca107882ce771f249842049dc55e55f334c675b | 2bbbf7b24648445e31d33a2a26f8618c2067bd23957587cc459f3c45a03ed48a | O=C1c2ccccc2C(=O)N1CCN1CCC(c2noc3ccccc23)CC1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D3;+0:5]1-O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10]-1:[c:11]>>[C:1]-[C:2]-[N;H0;D3;+0:3]1-[C;H0;D3;+0:5](=[O;D1;H0:4])-[c:10](:[c:11]):[c:8](:[c:9])-[C;H0;D3;+0:6]-1=[O;D1;H0:7] | null | [] | null | null | 3 | HOUR | A stirred mixture of 2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethylamine (2.63 g, 0.01 mole) and 4-nitrophthalic anhydride (1.93 g, 0.01 mole) in dichloromethane (200 ml) is stirred at room temperature for 3 hours. The solvent is then removed under reduced pressure and the residual material is purified by fl... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Substituted dicarboximide | c1ccc2c(c1)COC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2.C1CC[NH]CC1.c1ccc2oncc2c1 | HO- | ClCCl | null | 3 | NCCN1CCC(c2noc3cc(F)ccc23)CC1.O=C1OC(=O)c2cc([N+](=O)[O-])ccc21>ClCCl>O=C1c2ccc([N+](=O)[O-])cc2C(=O)N1CCN1CCC(c2noc3cc(F)ccc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-24d57af412c04f3eb1d3565ef87c50ca | CCOC(=O)CCN1CCC(c2noc3cc(F)ccc23)CC1.CCOC(C)=O>>CC(C)(O)CCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | [NH4+].[Cl-].CCOC(=O)C.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC(=O)OCC)C=C1.C[Mg]Br>>C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCC(C)(O)C)C=C1 | C([CH3:3])[O:4][C:2]([CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([F:17])[cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1)=[O:23].[CH2:24]([O:25][C:28]([CH3:27])=[O:29])[CH3:26]>>[CH3:1][C:2]([CH3:3])([OH:4])[CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([c:11]2[n:12][o:13][c:14]3[cH:15][c:16]([... | CCOC(=O)CCN1CCC(c2noc3cc(F)ccc23)CC1.CCOC(C)=O | CC(C)(O)CCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O | null | null | O1CCCC1 | Functional Group Addition | OtherReaction | 07e99f91e500affa0451dbbfb1ccdfc6c2bf1d992b11b74db56debe2dbd4b3e4 | 15308189f1479c7a0725eea178834fcdf99915b1d89a0f1b88a28657dab684ab | c1ccc2c(C3CCNCC3)noc2c1 | [CH3;D1;+0:1]-[CH2;D2;+0:2]-[O;H0;D2;+0:3]-[C;H0;D3;+0:4](-[CH3;D1;+0:5])=[O;D1;H0:6].[C:7]-[C:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[O;H0;D2;+0:11]-C-[CH3;D1;+0:12]>>[C:7]-[C:8]-[C;H0;D4;+0:9](-[C;D1;H3:13])(-[CH3;D1;+0:12])-[OH;D1;+0:11].[O;D1;H0:6]=[C;H0;D3;+0:4](-[O;D1;H1:14])/[CH;D2;+0:5]=[CH;D2;+0:1]/[C;H0;D3;+0:2]... | null | [] | null | null | 16 | HOUR | To a solution of ethyl 3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propionate (3.21 gm, 10 mmoles) in tetrahydrofuran (THF, 100 ml), methylmagnesium bromide (10 ml, 30 moles, 3M solution in ether) was added dropwise over 15 minutes at room temperature under N2. The resulting mixture was stirred for 16 hours. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid.Tertiary alcohol | null | null | C1CC[NH]CC1.c1ccc2oncc2c1 | Other | O1CCCC1 | null | 16 | CCOC(=O)CCN1CCC(c2noc3cc(F)ccc23)CC1.CCOC(C)=O>O1CCCC1>CC(C)(O)CCN1CCC(c2noc3cc(F)ccc23)CC1.O=C(O)/C=C/C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-16738fd4d2a14dc786bb52e64ff9fd58 | CCOCCl.Nc1cccc(O)c1>>CCOCOc1cccc(N)c1 | C(C)OCCl.[H-].[Na+].NC=1C=C(C=CC1)O>>C(C)OCOC=1C=C(C=CC1)N | Cl[CH2:4][O:3][CH2:2][CH3:1].[OH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([NH2:11])[cH:12]1>>[CH3:1][CH2:2][O:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([NH2:11])[cH:12]1 | CCOCCl.Nc1cccc(O)c1 | CCOCOc1cccc(N)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 6e90ffbf0683e1a3ee55c5e3ea453aefc5ddd369c0150ed0150f9546d7e47f4f | efd670663709b79afcad1306da9f69b33a0147cfa3639ca4c0b54b35ef4b1852 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 0 | CELSIUS | 3 | HOUR | A dispersion of 12 g (274.9 mmol) of sodium hydride (55% in oil) was added portionwise at 0° C. to a solution of 20.0 g (183.3 mmol) of 3-aminophenol in 450 mL of dried acetonitrile. The mixture was then allowed to agitate at 0° C. for 3 hours. A solution of 25 g (210.8 mmol) of chloromethyl ethyl ether in 30 mL of ace... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol | Ether.Ether | null | null | c1ccccc1 | HCl | C(C)#N | 0 | 3 | CCOCCl.Nc1cccc(O)c1>C(C)#N>CCOCOc1cccc(N)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b608a34733c04a159168cf9668226fb4 | O=[N+]([O-])[O-].[Al+3]>>O=[N+]([O-])[O-].[Al+3] | O.[N+](=O)([O-])[O-].[Al+3].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-]>>[N+](=O)([O-])[O-].[Al+3].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-] | [O:5]=[N+:6]([O-:7])[O-:8].[Al+3:13]>>[O:5]=[N+:6]([O-:7])[O-:8].[Al+3:13] | O=[N+]([O-])[O-].[Al+3] | O=[N+]([O-])[O-].[Al+3] | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | 375.13 g (1 mol) of aluminum nitrate hydrate [Al(NO3)3.9H2O, manufactured by Wako Pure Chemical Industries Ltd., guaranteed reagent] was dissolved in 777.87 g of pure water, to obtain 1000 cm3 of an aluminum nitrate aqueous solution. To 100 cm3 of the aluminum nitrate aqueous solution was added 2.83 g of the above-ment... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | null | null | O=[N+]([O-])[O-].[Al+3]>O>O=[N+]([O-])[O-].[Al+3] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ab66ece575e14f4f88417ae953a68374 | O=C(O)c1ccccc1O>>O=C(O)c1ccccc1O | C(O)CN.C(C=1C(O)=CC=CC1)(=O)O.C(O)CN.C(C=1C(O)=CC=CC1)(=O)O.C(O)CN.C(C=1C(O)=CC=CC1)(=O)O>>C(C=1C(O)=CC=CC1)(=O)O.C(O)CN | [O:5]=[C:6]([OH:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14]>>[O:5]=[C:6]([OH:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[OH:14] | O=C(O)c1ccccc1O | O=C(O)c1ccccc1O | null | null | C(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | null | null | In a 100 ml glass, heat 50 g of ethyl alcohol (C16H34O) to 40° C. and maintain temperature. Slowly add, while stirring, 5 g of salicylic acid (C7H6O3) until dissolved. Add 2 g of monoethanolamine (C2H7NO) until completely mixed. Repeat above process of sequentially adding salicylic acid and monoethanolamine until a tot... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | C(C)O | null | null | O=C(O)c1ccccc1O>C(C)O>O=C(O)c1ccccc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e390010f5a66490cb26092ec478635e2 | NCCO>>NCCO | C(C(O)C)(=O)O.C(O)CN>>C(C(O)C)(=O)O.C(O)CN | [NH2:7][CH2:8][CH2:9][OH:10]>>[NH2:7][CH2:8][CH2:9][OH:10] | NCCO | NCCO | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | In a 100 ml glass, heat 50 g of distilled water to 40° C. and maintain temperature. Add 18 g of lactic acid (C3H6O3). Test pH and slowly add monoethanolamine (C2H7NO) until a pH of 7.0 is achieved.
Conditions: See reaction.notes.procedure_details.
Workup: maintain temperature | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | null | null | NCCO>O>NCCO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-091c27d4f7224d0588963ff866073830 | CC(C)(C)[Si](C)(C)Cl.CC1=C[C@H]2O[C@@H]3C[C@H]4OC(=O)/C=C\C=C\[C@H]([C@@H](C)O)OCC[C@@H](C)[C@H](O)C(=O)OC[C@@]2(CC1)[C@]4(C)[C@]31CO1>>CC(=O)[O-].CCCCCC | N1C=NC=C1.C[C@@H]1CCO[C@H](/C=C/C=C\C(=O)O[C@@H]2C[C@@H]3[C@]4([C@]2([C@]5(CCC(=C[C@H]5O3)C)COC(=O)[C@H]1O)C)CO4)[C@@H](C)O.[Si](C)(C)(C(C)(C)C)Cl>>C(C)(=O)[O-].CCCCCC | CC(C)(C)[Si](C)(Cl)[CH3:10].C[C@@H]1CCO[C@@H]([C@@H](C)[OH:4])/C=C/C=C\C(=[O:3])O[C@@H]2C[C@H:5]3O[C@@H:8]4[CH:7]=[C:2]([CH3:1])CC[C@:9]4(COC(=O)[C@H]1O)[C@]2(C)[C@:6]31CO1>>[CH3:1][C:2](=[O:3])[O-:4].[CH3:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10] | CC(C)(C)[Si](C)(C)Cl.CC1=C[C@H]2O[C@@H]3C[C@H]4OC(=O)/C=C\C=C\[C@H]([C@@H](C)O)OCC[C@@H](C)[C@H](O)C(=O)OC[C@@]2(CC1)[C@]4(C)[C@]31CO1 | CC(=O)[O-].CCCCCC | null | null | CN(C=O)C | Acylation | OtherReaction | c8232f623ab73fbf3810b05a736c00e1f43fa1c847c2d009e4183f9615ca7dff | d06328b0c6e4b8bb67b99325c4e743e8e3912b9c8541c8956dcd0b540634f10c | null | null | 49 | [{"value": 49.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | null | null | Preparation of 13′-O-tert-butyldimethylsilyl-Roridin A. 100 mg (1.47 mmol) of imidazole was added to a solution of 232 mg (0.436 mmol) of Roridin A in 3 ml of dry dimethylformamide. The mixture was cooled to −5° C. and then 72 mg (0.478 mmol) of tert-butyldimethylsilyl chloride (Aldrich Chemical Co.) was added. The res... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ether.Ether.Ether.Secondary alcohol.Secondary alcohol.Conjugated diene.Silyl protective group | null | C1=C[C@H]2O[C@@H]3C[C@H]4OC/C=C\C=C\COCCCCCOC[C@@]2(CC1)[C@@H]4[C@]31CO1 | null | null | HCl | CN(C=O)C | -5 | null | CC(C)(C)[Si](C)(C)Cl.CC1=C[C@H]2O[C@@H]3C[C@H]4OC(=O)/C=C\C=C\[C@H]([C@@H](C)O)OCC[C@@H](C)[C@H](O)C(=O)OC[C@@]2(CC1)[C@]4(C)[C@]31CO1>CN(C=O)C>CC(=O)[O-].CCCCCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-09ab9db1af874cec8afef85218a51322 | C[C@@H](NC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21)C(=O)O.O=C1CCC(=O)N1O>>O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21 | C(CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12)(=O)N[C@H](C)C(=O)O.ON1C(CCC1=O)=O.N[C@H](C)C(=O)O.N[C@H](C)C(=O)O.Cl.CN(CCCN=C=NCC)C.ON1C(CCC1=O)=O.C1CN(CCN(CCN(CCN1CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O.NC1=CC=CC=C1>>C1CN(CCN(CCN(CCN1CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O.OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12 | C[C@@H](N[C:2](=[O:1])[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:8]1[S:9][CH2:10][C@@H:11]2[NH:12][C:13](=[O:14])[NH:15][C@H:16]12)C(=O)O.O=C1CCC(=O)N1[OH:3]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:8]1[S:9][CH2:10][C@@H:11]2[NH:12][C:13](=[O:14])[NH:15][C@H:16]12 | C[C@@H](NC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21)C(=O)O.O=C1CCC(=O)N1O | O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21 | null | null | null | Protection | OtherReaction | 543cca1236900bb17bf1a8c15e07d003211565da567f1ebfb51f915575e6f61e | b784e02ce9726a9c587d2fe85af8e013bee9ce99cbd3e00a5a9731977fbc070a | O=C1N[C@H]2CSC[C@H]2N1 | C-[C@@H](-N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4])-C(-O)=O.O=C1-C-C-C(=O)-N-1-[OH;D1;+0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[OH;D1;+0:5] | null | [] | null | null | null | null | The D-alanine-linked conjugate was prepared by first coupling D-alanine (Sigma Chemical Co.) to biotin-NHS ester. The resultant biotinyl-D-alanine was then activated with 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDCI) and N-hydroxysuccinimide (NHS). This NHS ester was reacted in situ with DOTA-anil... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amide.Tertiary amide.Tertiary amide | Carboxylic acid | C1CCNC1 | null | C1N[C@H]2CSC[C@H]2N1 | HO- | null | null | null | C[C@@H](NC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21)C(=O)O.O=C1CCC(=O)N1O>>O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6f2c79ee34a843c588714067f901ff68 | CNCC(=O)O.O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21>>CNCC(=O)C(CCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21)C(=O)O | C1CN(CCN(CCN(CCN1CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O.OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12.CNCC(=O)O.C1CN(CCN(CCN(CCN1CC(=O)O)CC(=O)O)CC(=O)O)CC(=O)O.OC(=O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12.CNCC(=O)O.N[C@H](C)C(=O)O>>CNCC(=O)C(C(O)=O)CCC[C@@H]1SC[C@@H]2NC(=O)N[C@H]12 | O[C:4]([CH2:3][NH:2][CH3:1])=[O:5].[CH2:6]([CH2:7][CH2:8][CH2:9][C@@H:10]1[S:11][CH2:12][C@@H:13]2[NH:14][C:15](=[O:16])[NH:17][C@H:18]12)[C:19](=[O:20])[OH:21]>>[CH3:1][NH:2][CH2:3][C:4](=[O:5])[CH:6]([CH2:7][CH2:8][CH2:9][C@@H:10]1[S:11][CH2:12][C@@H:13]2[NH:14][C:15](=[O:16])[NH:17][C@H:18]12)[C:19](=[O:20])[OH:21] | CNCC(=O)O.O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21 | CNCC(=O)C(CCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21)C(=O)O | null | null | C(C)N(CC)CC.CN(C)C=O | C-C Coupling | OtherReaction | c7f5ceb44a158fca900911601e13571b0c23016ff9943f5f31fa4dc39e0733d6 | a49756d2995b35bf1c4b6840928f031562470ef5bd676447fb43ce2575147daa | O=C1N[C@H]2CSC[C@H]2N1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[C:5]-[C:6]-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[O;D1;H1:10]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:7](-[C:6]-[C:5])-[C:8](=[O;D1;H0:9])-[O;D1;H1:10] | null | [] | null | null | null | null | The N-methyl glycine-linked DOTA-biotin conjugate was prepared by an analogous method to that used to prepare D-alanine-linked DOTA-biotin conjugates. N-methyl-glycine (trivial name sarcosine, available from Sigma Chemical Co.) was condensed with biotin-NHS ester in DMF and triethylamine to obtain N-methyl glycyl-bioti... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | null | null | C1N[C@H]2CSC[C@H]2N1 | HO- | C(C)N(CC)CC.CN(C)C=O | null | null | CNCC(=O)O.O=C(O)CCCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21>C(C)N(CC)CC.CN(C)C=O>CNCC(=O)C(CCC[C@@H]1SC[C@@H]2NC(=O)N[C@@H]21)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1ada602000694563b5e654f716cc2616 | NCCN(CCN)CCN.O=Cc1ccc[nH]1>>NCCN=Cc1ccc[nH]1 | N1C(=CC=C1)C=O.NCCN(CCN)CCN.O.[N+](=O)([O-])[O-].[Ga+3].[N+](=O)([O-])[O-].[N+](=O)([O-])[O-]>>N1C(=CC=C1)C=NCCN | NCC[N:4](CCN)[CH2:3][CH2:2][NH2:1].O=[CH:5][c:6]1[cH:7][cH:8][cH:9][nH:10]1>>[NH2:1][CH2:2][CH2:3][N:4]=[CH:5][c:6]1[cH:7][cH:8][cH:9][nH:10]1 | NCCN(CCN)CCN.O=Cc1ccc[nH]1 | NCCN=Cc1ccc[nH]1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 5bb9c36afdb852f191d9594668534907f259dfeb583790227b1a574002b4e65b | 5c8cd5b23108f7c707e25ca3918d21afec7c9f4fa7304db3754585c916616b1b | c1cc[nH]c1 | N-C-C-[N;H0;D3;+0:1](-C-C-N)-[C:2]-[C:3].O=[CH;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[C:3]-[C:2]-[N;H0;D2;+0:1]=[CH;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8] | null | [] | null | null | 30 | MINUTE | The ligand [(((pyrrole-2-yl)methylidene)amino)ethyl]amine was prepared by adding a methanolic solution of pyrrole-2-carboxaldehyde (1.430 g, 15 mmol, 100 mL) to a methanolic solution of tris(2-aminoethyl)amine (0.720 g, 5 mmol, 10 mL). The resulting yellow solution was stirred at room temperature for 30 min. A methanol... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Primary amine.Tertiary amine | Substituted imine | null | null | c1cc[nH]c1 | HO- | null | null | 0.5 | NCCN(CCN)CCN.O=Cc1ccc[nH]1>>NCCN=Cc1ccc[nH]1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ece6613157344bb187f4933ca95baeda | C=CC(=O)OCCCC.C=Cc1ccccc1>>C.C=Cc1ccccc1C=C | C=CC1=CC=CC=C1.C(C=C)(=O)OCCCC>>C(=C)C1=C(C=CC=C1)C=C.C | O=C(C=[CH2:2])O[CH2:5]CC[CH3:1].[cH:3]1[cH:4][c:9]([CH:10]=[CH2:11])[cH:8][cH:7][cH:6]1>>[CH4:1].[CH2:2]=[CH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[CH:10]=[CH2:11] | C=CC(=O)OCCCC.C=Cc1ccccc1 | C.C=Cc1ccccc1C=C | null | null | null | C-C Coupling | OtherReaction | 332e40b06097a8e57aa0a40e096053d40e54a716c6cf2fb9a4bd519069c2082d | 2644636eb772ef30c3c03a169846da42c5eac653f3889977ab8870ecd4f5a157 | c1ccccc1 | O=C(-C=[CH2;D1;+0:1])-O-[CH2;D2;+0:2]-C-C-[CH3;D1;+0:3].[C;D1;H2:4]=[C:5]-[c:6]1:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:1>>[C;D1;H2:4]=[C:5]-[c:6]1:[c:7]:[c:8]:[cH;D2;+0:9]:[cH;D2;+0:2]:[c;H0;D3;+0:11]:1-[CH;D2;+0:10]=[CH2;D1;+0:1].[CH4;D0;+0:3] | null | [] | null | null | null | null | A polymerizable monomer consisting of 80.5 parts of styrene and 19.5 parts of n-butyl acrylate (Tg of the copolymer obtained by copolymerizing these monomers=55° C.), 0.3 part of polymethacrylic acid ester macromonomer (manufactured by Toagosei Co., Ltd.; trade name: AA6; Tg=94° C.), 0.5 part of divinyl benzene, 1.2 pa... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Vinyl | Vinyl | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | null | C=CC(=O)OCCCC.C=Cc1ccccc1>>C.C=Cc1ccccc1C=C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0465103634f94e318ae0c256b9e2a45a | C=Cc1ccccc1>>C=Cc1ccccc1 | C=CC1=CC=CC=C1.COCCO.[Cl-].C(=C)C[N+](C)(C)CC1=CC=CC=C1>>C=CC1=CC=CC=C1.[Cl-].C(=C)C[N+](C)(C)CC1=CC=CC=C1 | [CH2:14]=[CH:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH2:14]=[CH:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | C=Cc1ccccc1 | C=Cc1ccccc1 | null | null | CCCCCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | 75 | CELSIUS | 2 | HOUR | Styrene (102.96 g) (0.99 mol), 44.2 g (0.21 mol) of vinylbenzyltrimethylammonium chloride and 446 g of 2-methoxy-ethanol were put in a three necked flask and heated at constant temperature of 75° C. with stirring under nitrogen gas flow. Thereafter, 76 g (12 mmol) of 2,2-azobis(dimethyl-2-isobutyrate) was added to the ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | CCCCCC | 75 | 2 | C=Cc1ccccc1>CCCCCC>C=Cc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9e45e151aa224cd2bbf20a160c7e8c1d | CCCC[CH2][Mg][Br].O=C(Cl)c1ccc(F)cc1>>CCCCCC(=O)c1ccc(F)cc1 | FC1=CC=C(C(=O)Cl)C=C1.C(CCCC)[Mg]Br.Cl>>FC1=CC=C(C=C1)C(CCCCC)=O | [Br][Mg][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].Cl[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1 | CCCC[CH2][Mg][Br].O=C(Cl)c1ccc(F)cc1 | CCCCCC(=O)c1ccc(F)cc1 | null | C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].[Fe+3] | O1CCCC1 | C-C Coupling | OtherReaction | ca01e82953d4193c8592b623fe014a93dd536ac2b9b6be24fdd2696e9d29c72c | 86a375217dac1e7e5af56ac35ada272b3baae86d3f59f8e623e6beaa450ef46e | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[Br]-[Mg]-[CH2;D2;+0:6]-[C:7]-[C:8]>>[C:8]-[C:7]-[CH2;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 100 mL of tetrahydrofuran was placed into a four-neck round-bottom flask, then 7.92 g (0.05 mol) of 4-fluorobenzoyl chloride and 0.53 g (1.5 mmol) of tris(acetylacetone)iron (III) were added and stirred under a nitrogen atmosphere. To this solution pentylmagnesium bromide was added at a room temperature and stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Magnesium halide | Ketone | null | null | c1ccccc1 | Br-.Mg | C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].[Fe+3].O1CCCC1 | null | null | CCCC[CH2][Mg][Br].O=C(Cl)c1ccc(F)cc1>C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].C/C(=C/C(=O)C)/[O-].[Fe+3].O1CCCC1>CCCCCC(=O)c1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-da622c2e851144e18b5e32b81f602c38 | NC(=O)c1ccc(Cl)cc1Cl.O=C(Cl)C(=O)Cl>>O=C=NC(=O)c1ccc(Cl)cc1Cl | ClC1=C(C(=O)N)C=CC(=C1)Cl.C(C(=O)Cl)(=O)Cl>>ClC1=C(C(=O)N=C=O)C=CC(=C1)Cl | [NH2:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]1[Cl:13].O=C(Cl)[C:2](Cl)=[O:1]>>[O:1]=[C:2]=[N:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([Cl:10])[cH:11][c:12]1[Cl:13] | NC(=O)c1ccc(Cl)cc1Cl.O=C(Cl)C(=O)Cl | O=C=NC(=O)c1ccc(Cl)cc1Cl | null | null | ClCCl | Miscellaneous | OtherReaction | cf02c1bb181b7aadb44446ed25edbc69c91d5a48ce29f9b928a8d564b5d912a5 | 90d98ee68a4149445e7f059170d2980413d9d8f59364f936e59a8702f0d050b3 | c1ccccc1 | Cl-C(=O)-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[NH2;D1;+0:3]-[C:4](=[O;D1;H0:5])-[c:6]>>[O;D1;H0:2]=[C;H0;D2;+0:1]=[N;H0;D2;+0:3]-[C:4](=[O;D1;H0:5])-[c:6] | null | [] | null | null | null | null | 2,4-Dichlorobenzamide was dissolved in dichloromethane, after which 1.5 eq. of oxalyl chloride were added and the mixture was heated to reflux for 16 hours. The reaction mixture was then concentrated under high vacuum and reacted in step b without any further purification.
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Primary amide | Isocyanate | null | null | c1ccccc1 | HCl | ClCCl | null | null | NC(=O)c1ccc(Cl)cc1Cl.O=C(Cl)C(=O)Cl>ClCCl>O=C=NC(=O)c1ccc(Cl)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a4215c2a13f74ffca2c62378fa5f5a43 | COc1ccc(C(=O)O)cc1N.O=C=NC(=O)c1ccc(Cl)cc1Cl>>COc1ccc(C(=O)O)cc1NC(=O)NC(=O)c1ccc(Cl)cc1Cl | NC=1C=C(C(=O)O)C=CC1OC.ClC1=C(C(=O)N=C=O)C=CC(=C1)Cl>>ClC1=C(C(=O)NC(NC=2C=C(C(=O)O)C=CC2OC)=O)C=CC(=C1)Cl | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]1[NH2:12].[C:13](=[O:14])=[N:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([Cl:22])[cH:23][c:24]1[Cl:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7](=[O:8])[OH:9])[cH:10][c:11]1[NH:12][C:13](=[O:14])[NH:15][C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]([Cl... | COc1ccc(C(=O)O)cc1N.O=C=NC(=O)c1ccc(Cl)cc1Cl | COc1ccc(C(=O)O)cc1NC(=O)NC(=O)c1ccc(Cl)cc1Cl | null | null | C(C)#N | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NC(=O)c1ccccc1)Nc1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4].[O;D1;H0:5]=[C;H0;D2;+0:6]=[N;H0;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]>>[O;D1;H0:5]=[C;H0;D3;+0:6](-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[NH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10] | 96 | [{"value": 96.0, "product": "ClC1=C(C(=O)NC(NC=2C=C(C(=O)O)C=CC2OC)=O)C=CC(=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.7, "product": "ClC1=C(C(=O)NC(NC=2C=C(C(=O)O)C=CC2OC)=O)C=CC(=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 20 g (120 mmol) of 3-amino-4-methoxybenzoic acid were made to react with 36 g (168 mmol) of 2,4-dichlorobenzoyl isocyanate from step a in 400 ml of acetonitrile and left to react therewith at reflux for 2 hours. After the mixture has cooled down to room temperature, the precipitate is filtered off with suction, washed ... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1ccccc1 | null | C(C)#N | null | null | COc1ccc(C(=O)O)cc1N.O=C=NC(=O)c1ccc(Cl)cc1Cl>C(C)#N>COc1ccc(C(=O)O)cc1NC(=O)NC(=O)c1ccc(Cl)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e8d135ce721f44c28b38da57cc1c2746 | COc1ccc(S)cc1.O=[N+]([O-])c1ccc(Cl)cc1>>COc1ccc(Sc2ccc([N+](=O)[O-])cc2)cc1 | COC1=CC=C(C=C1)S.[H-].[Na+].ClC1=CC=C(C=C1)[N+](=O)[O-]>>COC1=CC=C(C=C1)SC1=CC=C(C=C1)[N+](=O)[O-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([SH:7])[cH:17][cH:18]1.Cl[c:8]1[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7][c:8]2[cH:9][cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16]2)[cH:17][cH:18]1 | COc1ccc(S)cc1.O=[N+]([O-])c1ccc(Cl)cc1 | COc1ccc(Sc2ccc([N+](=O)[O-])cc2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution thiol | 58418ec60768d81d36d89dd63ae654278dbe4f345ecf281628c70cd9ed7fe768 | 97e4acce9b485bd597e518526ab4e9623782b1c9043b6e30dd257d386e3e5b01 | c1ccc(Sc2ccccc2)cc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[SH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[S;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]):[c:2]:[c:3] | 96.8 | [{"value": 96.0, "product": "COC1=CC=C(C=C1)SC1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.8, "product": "COC1=CC=C(C=C1)SC1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | To a suspension of NaH (4.2 g) in 100 mL of dry DMF under nitrogen was slowly added 14.02 g of 4-methoxythiophenol. The reaction mix was stirred until no further gas evolution occurred (circa 20 minutes). To this solution was added 15.76 g of 4-chloronitrobenzene dissolved in 100 ml of dry DMF, after which the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic thiol | Monosulfide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | 120 | null | COc1ccc(S)cc1.O=[N+]([O-])c1ccc(Cl)cc1>CN(C)C=O>COc1ccc(Sc2ccc([N+](=O)[O-])cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9dd4fd30ac414a2e8efe65060324f68e | COc1ccc(Sc2ccc([N+](=O)[O-])cc2)cc1>>COc1ccc(Sc2ccc(N)cc2)cc1 | COC1=CC=C(C=C1)SC1=CC=C(C=C1)[N+](=O)[O-]>>COC1=CC=C(C=C1)SC1=CC=C(C=C1)N | O=[N+:12]([O-])[c:11]1[cH:10][cH:9][c:8]([S:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:16][cH:15]2)[cH:14][cH:13]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([S:7][c:8]2[cH:9][cH:10][c:11]([NH2:12])[cH:13][cH:14]2)[cH:15][cH:16]1 | COc1ccc(Sc2ccc([N+](=O)[O-])cc2)cc1 | COc1ccc(Sc2ccc(N)cc2)cc1 | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Sc2ccccc2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 68.1 | [{"value": 68.0, "product": "COC1=CC=C(C=C1)SC1=CC=C(C=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.1, "product": "COC1=CC=C(C=C1)SC1=CC=C(C=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 13.06 g of 4-(4-methoxy-phenylsulfanyl)-nitrobenzene from step 1 in 100 mL of ethanol was added 33.85 g of SnCl2−2H2O. The resulting mixture was stirred for 30 minutes at room temperature, then heated to reflux for 2 hours. The mixture was then cooled to room temperature, concentrated in vacuo, and tre... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | C(C)O | null | 0.5 | COc1ccc(Sc2ccc([N+](=O)[O-])cc2)cc1>C(C)O>COc1ccc(Sc2ccc(N)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-819fdb30593b4783b14fd368375a0969 | N#Cc1ccc(Sc2ccc(Cl)cc2)cc1>>NCc1ccc(Sc2ccc(Cl)cc2)cc1 | ClC1=CC=C(C=C1)SC1=CC=C(C#N)C=C1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>ClC1=CC=C(C=C1)SC1=CC=C(CN)C=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([S:7][c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[cH:15][cH:16]1>>[NH2:1][CH2:2][c:3]1[cH:4][cH:5][c:6]([S:7][c:8]2[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]2)[cH:15][cH:16]1 | N#Cc1ccc(Sc2ccc(Cl)cc2)cc1 | NCc1ccc(Sc2ccc(Cl)cc2)cc1 | null | null | C1CCOC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1ccc(Sc2ccccc2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 93.6 | [{"value": 93.6, "product": "ClC1=CC=C(C=C1)SC1=CC=C(CN)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | To a solution of 4-(4-chloro-phenylsulfanyl)-benzonitrile (4.91 g) in 100 mL of dry THF under nitrogen stirring at room temperature was added 40 mL of lithium aluminum hydride solution (1.0 M in THF) via syringe. The reaction mix was allowed to stir for 3.5 hours at room temperature, and was then heated to reflux for 4... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.c1ccccc1 | null | C1CCOC1 | null | 3.5 | N#Cc1ccc(Sc2ccc(Cl)cc2)cc1>C1CCOC1>NCc1ccc(Sc2ccc(Cl)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-787609c5fc094e55af8b9d71496b9fb7 | O=Cc1ccc(O)cc1.OCCC1CCN(c2ccc(Cl)nn2)CC1>>O=Cc1ccc(OCCC2CCCCN2c2ccc(Cl)nn2)cc1 | OC1=CC=C(C=O)C=C1.ClC1=CC=C(N=N1)N1CCC(CC1)CCO.C(C)O>>ClC1=CC=C(N=N1)N1C(CCCC1)CCOC1=CC=C(C=O)C=C1 | [O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[cH:23][cH:24]1.O[CH2:8][CH2:9][CH:10]1[CH2:11][CH2:12][N:15]([c:16]2[cH:17][cH:18][c:19]([Cl:20])[n:21][n:22]2)[CH2:14][CH2:13]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][N:15]2[c:16]2[cH:17][cH:18][c:19]([Cl:20])[n:21][n... | O=Cc1ccc(O)cc1.OCCC1CCN(c2ccc(Cl)nn2)CC1 | O=Cc1ccc(OCCC2CCCCN2c2ccc(Cl)nn2)cc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 0f06477de7cd0c35e538a8fa5bdf57f341aa4a1ddd11263adeb94973dcb5a072 | 65d9257b508e1839cdbbf508d968410ece9529492834fd6acdca7e25f839a3f0 | c1ccc(OCCC2CCCCN2c2cccnn2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[CH;D3;+0:3]1-[C:4]-[CH2;D2;+0:5]-[N;H0;D3;+0:6](-[c:7](:[c:8]):[#7;a:9]:[#7;a:10]:[c:11])-[C:12]-[CH2;D2;+0:13]-1.[OH;D1;+0:14]-[c:15](:[c:16]):[c:17]>>[c:8]:[c:7](-[N;H0;D3;+0:6]1-[C:12]-[CH2;D2;+0:13]-[CH2;D2;+0:5]-[C:4]-[CH;D3;+0:3]-1-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:14]-[c:15](:[c:16]):[c:17])... | 44 | [{"value": 44.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4- {2-[1-(6-Chloro-3-pyridazinyl)piperidinyl]ethoxy}benzaldehyde (Intermediate IIa) was prepared from 4-hydroxybenzaldehyde and 2-[1-(6-Chloro-3-pyridazinyl)-4-piperidinyl]ethanol using a Mitsunobu Reaction and following the general methods described in U.S. Pat. No. 4,992,433. The aldehyde (60 mg, 0.17 mmol) was disso... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol.Tertiary amine | Ether.Tertiary amine | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1.c1ccnnc1 | HO- | O | null | null | O=Cc1ccc(O)cc1.OCCC1CCN(c2ccc(Cl)nn2)CC1>O>O=Cc1ccc(OCCC2CCCCN2c2ccc(Cl)nn2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-631c2fe64f044b65aedaec9cf6bcb544 | CCON.O=Cc1ccc(O)cc1>>CCON=Cc1ccc(O)cc1 | OC1=CC=C(C=O)C=C1.C(C)ON.ClCCl>>C(C)ON=CC1=CC=C(C=C1)O | [CH3:1][CH2:2][O:3][NH2:4].O=[CH:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:11][cH:12]1>>[CH3:1][CH2:2][O:3][N:4]=[CH:5][c:6]1[cH:7][cH:8][c:9]([OH:10])[cH:11][cH:12]1 | CCON.O=Cc1ccc(O)cc1 | CCON=Cc1ccc(O)cc1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 54882f986dad145756472fc79464161665827db6af7b3780cb2b83c72b495424 | 3d6c7b6a0f29252ce5dcda36fa3ef05efc366c421f47850a88ae430c686fc79d | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[NH2;D1;+0:7]>>[C:5]-[#8:6]-[N;H0;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 92.5 | [{"value": 92.5, "product": "C(C)ON=CC1=CC=C(C=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.0, "product": "C(C)ON=CC1=CC=C(C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-hydroxybenzaldehyde (100 mg, 0.88 mmol) and 50% O-ethylhydroxylamine aqueous solution (0.6 ml, 4.9 mmol) in dioxane (2 ml) was stirred under an atmosphere of argon at room temperature for 16 hours and then heated at 90-100° for 3 hours when thin layer chromatography (silica, dichloromethane) indicated t... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | null | null | null | c1ccccc1 | HO- | O1CCOCC1 | null | null | CCON.O=Cc1ccc(O)cc1>O1CCOCC1>CCON=Cc1ccc(O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-81fb2facae8544069721ab1464838751 | C#CCCCO.CCON=Cc1cc(C)c(O)c(C)c1>>C#CCCCOc1c(C)cc(C=NOCC)cc1C | C(CCC#C)O.C(C)ON=CC1=CC(=C(C(=C1)C)O)C>>C(C)ON=CC1=CC(=C(C(=C1)C)OCCCC#C)C | O[CH2:5][CH2:4][CH2:3][C:2]#[CH:1].[OH:6][c:7]1[c:8]([CH3:9])[cH:10][c:11]([CH:12]=[N:13][O:14][CH2:15][CH3:16])[cH:17][c:18]1[CH3:19]>>[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][O:6][c:7]1[c:8]([CH3:9])[cH:10][c:11]([CH:12]=[N:13][O:14][CH2:15][CH3:16])[cH:17][c:18]1[CH3:19] | C#CCCCO.CCON=Cc1cc(C)c(O)c(C)c1 | C#CCCCOc1c(C)cc(C=NOCC)cc1C | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]#[C;D1;H1:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[C;D1;H1:5]#[C:4]-[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9] | null | [] | null | null | null | null | Condensation of 4-pentyn-1-ol and 4-hydroxy-3,5-dimethylbenzaldehyde O-ethyloxime using Mitsunobu Reaction conditions (see for example J. Med. Chem., 36, 3240, 1993 and references cited therein) gave 3,5-dimethyl4-(4-pentyn-1-yloxy)benzaldehyde O-ethyl oxime in good yield.
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1 | HO- | null | null | null | C#CCCCO.CCON=Cc1cc(C)c(O)c(C)c1>>C#CCCCOc1c(C)cc(C=NOCC)cc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9a6681b884134483bf8b684de6addf88 | C#CCCCOc1c(C)cc(C=NOCC)cc1C.ON=Cc1ccccc1>>CCON=Cc1cc(C)c(OCCCc2cc(-c3ccccc3)no2)c(C)c1 | C(C)N(CC)CC.C(C)ON=CC1=CC(=C(C(=C1)C)OCCCC#C)C.C(C1=CC=CC=C1)=NO.ClN1C(CCC1=O)=O>>C(C)ON=CC1=CC(=C(C(=C1)C)OCCCC1=CC(=NO1)C1=CC=CC=C1)C | [CH3:1][CH2:2][O:3][N:4]=[CH:5][c:6]1[cH:7][c:8]([CH3:9])[c:10]([O:11][CH2:12][CH2:13][CH2:14][C:15]#[CH:16])[c:26]([CH3:27])[cH:28]1.[CH:17]([c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)=[N:24][OH:25]>>[CH3:1][CH2:2][O:3][N:4]=[CH:5][c:6]1[cH:7][c:8]([CH3:9])[c:10]([O:11][CH2:12][CH2:13][CH2:14][c:15]2[cH:16][c:17](-[c... | C#CCCCOc1c(C)cc(C=NOCC)cc1C.ON=Cc1ccccc1 | CCON=Cc1cc(C)c(OCCCc2cc(-c3ccccc3)no2)c(C)c1 | null | N1=CC=CC=C1 | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 16b6cd102ecd71fbe2a5e7bfcc7c52ec8c6ac47b948d2e926aa77fed51055f5c | d59db5f5144aec61a5a64ca529856dc804630d654f00918274d989b69216eb79 | c1ccc(OCCCc2cc(-c3ccccc3)no2)cc1 | [C:1]-[C:2]-[C;H0;D2;+0:3]#[CH;D1;+0:4].[OH;D1;+0:5]-[N;H0;D2;+0:6]=[CH;D2;+0:7]-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[C:1]-[C:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[c;H0;D3;+0:7](-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]):[n;H0;D2;+0:6]:[o;H0;D2;+0:5]:1 | 32 | [{"value": 32.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | A solution of benzaldehyde oxime (45 mg, 0.372 mmol) in DMF (0.5 ml) was added dropwise to a solution of N-chlorosuccinimide (50 mg, 0.374 mmol) and pyridine (1 drop) in DMF (0.5 ml), keeping the temperature between 25-30° C. The resulting solution was allowed to stir at room temperature for 90 minutes. To this was add... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Oxime | null | null | c1cnoc1 | c1ccccc1.c1cnoc1.c1ccccc1 | null | N1=CC=CC=C1.CN(C)C=O | null | 1.5 | C#CCCCOc1c(C)cc(C=NOCC)cc1C.ON=Cc1ccccc1>N1=CC=CC=C1.CN(C)C=O>CCON=Cc1cc(C)c(OCCCc2cc(-c3ccccc3)no2)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-67d1d9cf48ee4a3e80ffd966c1a31e3d | CC(C)(C)[Si](C)(C)OCc1csc(Cl)n1>>CC(C)(C)[Si](C)(C)OCc1cscn1 | ClC=1SC=C(N1)CO[Si](C)(C)C(C)(C)C.[H-].[Na+].CC1=CC=C(N=N1)N1CCC(CC1)CCO>>[Si](C)(C)(C(C)(C)C)OCC=1N=CSC1 | Cl[c:13]1[s:12][cH:11][c:10]([CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[n:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][c:10]1[cH:11][s:12][cH:13][n:14]1 | CC(C)(C)[Si](C)(C)OCc1csc(Cl)n1 | CC(C)(C)[Si](C)(C)OCc1cscn1 | null | null | CCOCC.C(OC)COC | Functional Group Interconversion | Aromatic dehalogenation | 4f6106989807e1170e2da8f2e1925119dcd1a22ece2cb0c7a904100c5bae54f5 | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | c1cscn1 | Cl-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1>>[#16;a:2]1:[c:3]:[c:4]:[#7;a:5]:[cH;D2;+0:1]:1 | 81.8 | [{"value": 54.0, "product": "[Si](C)(C)(C(C)(C)C)OCC=1N=CSC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.8, "product": "[Si](C)(C)(C(C)(C)C)OCC=1N=CSC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A suspension of sodium hydride (60%, 135 mg, 3.4 mmol) and 1-(6-methyl-3-pyridazinyl)-4-(2-hydroxyethyl)-piperidine (250 mg, 1.1 mmol) in dimethoxyethane (DME; 4 ml) was stirred at room temperature for 2 hr. A solution of 2-chloro-4-t-butyldimethylsilyloxymethylthiazole (385 mg, 1.46 mmol) in DME (1 ml) was added and t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cscn1 | c1cscn1 | c1cscn1 | Other | CCOCC.C(OC)COC | null | 2 | CC(C)(C)[Si](C)(C)OCc1csc(Cl)n1>CCOCC.C(OC)COC>CC(C)(C)[Si](C)(C)OCc1cscn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7b93615a1aee4f05861c3a6bb484f95d | Clc1ccnnc1Cl.NCCCCCO>>OCCCCCNc1ccc(Cl)nn1 | NCCCCCO.ClC1=C(N=NC=C1)Cl.C([O-])([O-])=O.[Na+].[Na+]>>ClC1=CC=C(N=N1)NCCCCCO | Cl[c:8]1[c:11]([Cl:12])[cH:10][cH:9][n:13][n:14]1.[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]>>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][c:8]1[cH:9][cH:10][c:11]([Cl:12])[n:13][n:14]1 | Clc1ccnnc1Cl.NCCCCCO | OCCCCCNc1ccc(Cl)nn1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 5aea7debdfe3eec85b0d59584066bcd465b3d955619b62e42ce7f0f0ee817111 | d6fde1e16668e06119c1512640e5d4978b03666a9981f61cec109523a7356b3c | c1ccnnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[n;H0;D2;+0:3]:[cH;D2;+0:4]:[c:5]:[c;H0;D3;+0:6]:1-[Cl;D1;H0:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[n;H0;D2;+0:3]:[c;H0;D3;+0:6](-[Cl;D1;H0:7]):[c:5]:[cH;D2;+0:4]:1 | 22 | [{"value": 22.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 5-amino-1-pentanol (433 mg, 4.2 mmol), dichloropyridazine (1.25 g, 8.39 mmol) and sodium carbonate (890 mg, 8.39 mmol) was stirred in 1,4-dioxane (40 ml) and heated at 70-80° for 3 days under an atmosphere of argon. The solvent was removed under reduced pressure and the residue was partitioned between dich... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary amine | Aromatic halide.Secondary amine | c1ccnnc1 | c1ccnnc1 | c1ccnnc1 | HCl | O1CCOCC1 | null | null | Clc1ccnnc1Cl.NCCCCCO>O1CCOCC1>OCCCCCNc1ccc(Cl)nn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-13dd3bfb9a69454a9e9066abb2cd96db | CI.O=Cc1ccc(OCCCCCNc2ccc(Cl)nn2)cc1>>CN(CCCCCOc1ccc(C=O)cc1)c1ccc(Cl)nn1 | O.[H-].[Na+].ClC1=CC=C(N=N1)NCCCCCOC1=CC=C(C=O)C=C1.CI>>ClC1=CC=C(N=N1)N(CCCCCOC1=CC=C(C=O)C=C1)C | I[CH3:1].[NH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH:13]=[O:14])[cH:15][cH:16]1)[c:17]1[cH:18][cH:19][c:20]([Cl:21])[n:22][n:23]1>>[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([CH:13]=[O:14])[cH:15][cH:16]1)[c:17]1[cH:18][cH:19][c:20]([Cl:21])[n:22][n... | CI.O=Cc1ccc(OCCCCCNc2ccc(Cl)nn2)cc1 | CN(CCCCCOc1ccc(C=O)cc1)c1ccc(Cl)nn1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e1587a52a1bca6a80c6048d43276d8bccf8d3e94e692e6b210e5fd3b22494187 | 7cc25fba33369069673bac5bd8fc404dc064da8d6c8cf4a77f21f4df0a617fe3 | c1ccc(OCCCCCNc2cccnn2)cc1 | I-[CH3;D1;+0:1].[C:2]-[C:3]-[NH;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]:[#7;a:8]:[c:9]>>[C:2]-[C:3]-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[c:5](:[c:6]):[#7;a:7]:[#7;a:8]:[c:9] | 30 | [{"value": 30.0, "product": "ClC1=CC=C(N=N1)N(CCCCCOC1=CC=C(C=O)C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.0, "product": "ClC1=CC=C(N=N1)N(CCCCCOC1=CC=C(C=O)C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Sodium hydride (10 mg, 0.24 mmol) was added to a solution of 4-{N-(6-Chloro-3-pyridazinyl)-5-aminopentan-1-oxy}benzaldehyde (51 mg, 0.16 mmol) in THF (3.5 ml) and the mixture was stirred at room temperature for 30 minutes. Methyl iodide (50 μl, 0.8 mmol) was added to the reaction mixture and the suspension was stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccnnc1 | HI | C1CCOC1 | null | 0.5 | CI.O=Cc1ccc(OCCCCCNc2ccc(Cl)nn2)cc1>C1CCOC1>CN(CCCCCOc1ccc(C=O)cc1)c1ccc(Cl)nn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6c0677b2b364456290183131bbb7d1a5 | CCON.CN(CCCCCOc1ccc(C=O)cc1)c1ccc(Cl)nn1>>CCON=Cc1ccc(OCCCCCN(C)c2ccc(Cl)nn2)cc1 | ClC1=CC=C(N=N1)N(CCCCCOC1=CC=C(C=O)C=C1)C.C(C)ON>>C(C)ON=CC1=CC=C(C=C1)OCCCCCN(C)C=1N=NC(=CC1)Cl | [CH3:1][CH2:2][O:3][NH2:4].O=[CH:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:17])[c:18]2[cH:19][cH:20][c:21]([Cl:22])[n:23][n:24]2)[cH:25][cH:26]1>>[CH3:1][CH2:2][O:3][N:4]=[CH:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]([CH3:17])[c:18]2[cH:19][... | CCON.CN(CCCCCOc1ccc(C=O)cc1)c1ccc(Cl)nn1 | CCON=Cc1ccc(OCCCCCN(C)c2ccc(Cl)nn2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 54882f986dad145756472fc79464161665827db6af7b3780cb2b83c72b495424 | 3d6c7b6a0f29252ce5dcda36fa3ef05efc366c421f47850a88ae430c686fc79d | c1ccc(OCCCCCNc2cccnn2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[NH2;D1;+0:7]>>[C:5]-[#8:6]-[N;H0;D2;+0:7]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | Reaction of 4-{N-(6-Chloro-3-pyridazinyl)-N-methyl-5-aminopentan-1-oxy}benzaldehyde with ethoxyamine following similar conditions to those in Example 1 gave 4-{N-(6-Chloro-3-pyridazinyl)-N-methyl-5-aminopentan-1-oxy}benzaldehyde O-ethyloxime (Compound 161) as a colourless oil. The nmr and mass spectral data are given b... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | null | null | null | c1ccccc1.c1ccnnc1 | HO- | null | null | null | CCON.CN(CCCCCOc1ccc(C=O)cc1)c1ccc(Cl)nn1>>CCON=Cc1ccc(OCCCCCN(C)c2ccc(Cl)nn2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c15051d52f544451954de1882d51f1db | Cc1nnc(Br)s1.OCCC1CCNCC1>>Cc1nnc(N2CCC(CCO)CC2)s1 | BrC=1SC(=NN1)C.N1CCC(CC1)CCO.C([O-])([O-])=O.[K+].[K+]>>CC1=NN=C(S1)N1CCC(CC1)CCO | Br[c:5]1[n:4][n:3][c:2]([CH3:1])[s:15]1.[NH:6]1[CH2:7][CH2:8][CH:9]([CH2:10][CH2:11][OH:12])[CH2:13][CH2:14]1>>[CH3:1][c:2]1[n:3][n:4][c:5]([N:6]2[CH2:7][CH2:8][CH:9]([CH2:10][CH2:11][OH:12])[CH2:13][CH2:14]2)[s:15]1 | Cc1nnc(Br)s1.OCCC1CCNCC1 | Cc1nnc(N2CCC(CCO)CC2)s1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | d5ef7977e5c684ef51d2ba431a770308c0f27af177e447e091c94f6e40be2275 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1nnc(N2CCCCC2)s1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[#7;a:6]:1.[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]>>[C:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[C;D1;H3:4]):[#7;a:5]:[#7;a:6]:1)-[C:10]-[C:11] | 32.2 | [{"value": 2.5, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.0, "product": "CC1=NN=C(S1)N1CCC(CC1)CCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.2, "product": "CC1=NN=C(S1)N1CCC(CC1)CCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A suspension containing 2-bromo-5-methyl-1,3,4-thiadiazole (Modarai, B., et al. J. Heterocyclic Chem. (1974) 11, 343-5) (100 mg, 0.56 mmol), 4-piperidine ethanol (87 mg, 0.67 mmol) and potassium carbonate (77 mg, 0.56 mmol) was heated overnight at 120° C. The reaction was cooled and the mixture partitioned between wate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1nncs1.C1CCNCC1 | c1nncs1.C1CC[NH]CC1 | c1nncs1.C1CC[NH]CC1 | HBr | null | 120 | null | Cc1nnc(Br)s1.OCCC1CCNCC1>>Cc1nnc(N2CCC(CCO)CC2)s1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3702316ac7f642d386c91c6e27215180 | Fc1ccc(Nc2ncnc3cc4c(cc23)OCCCSCCCO4)cc1Cl>>O=S1(=O)CCCOc2cc3ncnc(Nc4ccc(F)c(Cl)c4)c3cc2OCCC1 | ClC=1C=C(C=CC1F)NC1=NC=NC2=CC=3OCCCSCCCOC3C=C12.OOS(=O)[O-].[K+].O>>ClC=1C=C(C=CC1F)NC1=NC=NC2=CC=3OCCCS(CCCOC3C=C12)(=O)=O | [S:2]1[CH2:4][CH2:5][CH2:6][O:7][c:8]2[cH:9][c:10]3[n:11][cH:12][n:13][c:14]([NH:15][c:16]4[cH:17][cH:18][c:19]([F:20])[c:21]([Cl:22])[cH:23]4)[c:24]3[cH:25][c:26]2[O:27][CH2:28][CH2:29][CH2:30]1>>[O:1]=[S:2]1(=[O:3])[CH2:4][CH2:5][CH2:6][O:7][c:8]2[cH:9][c:10]3[n:11][cH:12][n:13][c:14]([NH:15][c:16]4[cH:17][cH:18][c:1... | Fc1ccc(Nc2ncnc3cc4c(cc23)OCCCSCCCO4)cc1Cl | O=S1(=O)CCCOc2cc3ncnc(Nc4ccc(F)c(Cl)c4)c3cc2OCCC1 | null | null | CO | Oxidation | OtherReaction | 5fe02016886a03efcab5c1a4819f1ae138af81a1684b126fdae0d8c1b4c10b19 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | O=S1(=O)CCCOc2cc3ncnc(Nc4ccccc4)c3cc2OCCC1 | [C:1]-[C:2]-[S;H0;D2;+0:3]-[C:4]-[C:5]>>[C:1]-[C:2]-[S;H0;D4;+0:3](=[O;D1;H0:6])(=[O;D1;H0:7])-[C:4]-[C:5] | null | [] | null | null | 4 | HOUR | (3-Chloro-4-fluoro-phenyl)-(2,10-dioxa-6-thia-14,16-diaza-tricyclo[9.8.0.013,18]nonadeca-1-(11),12,14,16,18-pentaen-17-yl)-amine (16, 140 mg, 0.33 mmol) was suspended in MeOH, to which was added a cloudy aqueous solution of oxone (monopersulfate compound) (820 mg, 1.33 mmol) at room temperature. The suspension was stir... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | c1ncc2cc3c(cc2n1)OCCCSCCCO3 | c1ncc2cc3c(cc2n1)OCCCSCCCO3 | c1ncc2cc3c(cc2n1)OCCCSCCCO3.c1ccccc1 | null | CO | null | 4 | Fc1ccc(Nc2ncnc3cc4c(cc23)OCCCSCCCO4)cc1Cl>CO>O=S1(=O)CCCOc2cc3ncnc(Nc4ccc(F)c(Cl)c4)c3cc2OCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cfcc94e67317414aafec216e4f7d7e4c | Clc1cccc(Nc2ncnc3cc4c(cc23)OCCCSCCCO4)c1>>O=S1(=O)CCCOc2cc3ncnc(Nc4cccc(Cl)c4)c3cc2OCCC1 | ClC=1C=C(C=CC1)NC1=NC=NC2=CC=3OCCCSCCCOC3C=C12.OOS(=O)[O-].[K+].O>>ClC=1C=C(C=CC1)NC1=NC=NC2=CC=3OCCCS(CCCOC3C=C12)(=O)=O | [S:2]1[CH2:4][CH2:5][CH2:6][O:7][c:8]2[cH:9][c:10]3[n:11][cH:12][n:13][c:14]([NH:15][c:16]4[cH:17][cH:18][cH:19][c:20]([Cl:21])[cH:22]4)[c:23]3[cH:24][c:25]2[O:26][CH2:27][CH2:28][CH2:29]1>>[O:1]=[S:2]1(=[O:3])[CH2:4][CH2:5][CH2:6][O:7][c:8]2[cH:9][c:10]3[n:11][cH:12][n:13][c:14]([NH:15][c:16]4[cH:17][cH:18][cH:19][c:2... | Clc1cccc(Nc2ncnc3cc4c(cc23)OCCCSCCCO4)c1 | O=S1(=O)CCCOc2cc3ncnc(Nc4cccc(Cl)c4)c3cc2OCCC1 | null | null | CO | Oxidation | OtherReaction | 5fe02016886a03efcab5c1a4819f1ae138af81a1684b126fdae0d8c1b4c10b19 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | O=S1(=O)CCCOc2cc3ncnc(Nc4ccccc4)c3cc2OCCC1 | [C:1]-[C:2]-[S;H0;D2;+0:3]-[C:4]-[C:5]>>[C:1]-[C:2]-[S;H0;D4;+0:3](=[O;D1;H0:6])(=[O;D1;H0:7])-[C:4]-[C:5] | null | [] | null | null | 4 | HOUR | (3-Chloro-phenyl)-(2,10-dioxa-6-thia-14,16-diaza-tricyclo[9.8.0.013,18]nonadeca-1(11),12,14,16,18-pentaen-17-yl)-amine (19, 100 mg, 0.23 mmol) was suspended in MeOH, to which was added a cloudy aqueous solution of oxone (monopersulfate compound) (551 mg, 0.897 mmol) at room temperature. The suspension was stirred and m... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | c1ncc2cc3c(cc2n1)OCCCSCCCO3 | c1ncc2cc3c(cc2n1)OCCCSCCCO3 | c1ncc2cc3c(cc2n1)OCCCSCCCO3.c1ccccc1 | null | CO | null | 4 | Clc1cccc(Nc2ncnc3cc4c(cc23)OCCCSCCCO4)c1>CO>O=S1(=O)CCCOc2cc3ncnc(Nc4cccc(Cl)c4)c3cc2OCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6e24601995134034850c72b8f5f7927b | Brc1cccc(Nc2ncnc3cc4c(cc23)OCCCSCCCO4)c1>>O=S1(=O)CCCOc2cc3ncnc(Nc4cccc(Br)c4)c3cc2OCCC1 | BrC=1C=C(C=CC1)NC1=NC=NC2=CC=3OCCCSCCCOC3C=C12.OOS(=O)[O-].[K+].O>>BrC=1C=C(C=CC1)NC1=NC=NC2=CC=3OCCCS(CCCOC3C=C12)(=O)=O | [S:2]1[CH2:4][CH2:5][CH2:6][O:7][c:8]2[cH:9][c:10]3[n:11][cH:12][n:13][c:14]([NH:15][c:16]4[cH:17][cH:18][cH:19][c:20]([Br:21])[cH:22]4)[c:23]3[cH:24][c:25]2[O:26][CH2:27][CH2:28][CH2:29]1>>[O:1]=[S:2]1(=[O:3])[CH2:4][CH2:5][CH2:6][O:7][c:8]2[cH:9][c:10]3[n:11][cH:12][n:13][c:14]([NH:15][c:16]4[cH:17][cH:18][cH:19][c:2... | Brc1cccc(Nc2ncnc3cc4c(cc23)OCCCSCCCO4)c1 | O=S1(=O)CCCOc2cc3ncnc(Nc4cccc(Br)c4)c3cc2OCCC1 | null | null | CO | Oxidation | OtherReaction | 5fe02016886a03efcab5c1a4819f1ae138af81a1684b126fdae0d8c1b4c10b19 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | O=S1(=O)CCCOc2cc3ncnc(Nc4ccccc4)c3cc2OCCC1 | [C:1]-[C:2]-[S;H0;D2;+0:3]-[C:4]-[C:5]>>[C:1]-[C:2]-[S;H0;D4;+0:3](=[O;D1;H0:6])(=[O;D1;H0:7])-[C:4]-[C:5] | null | [] | null | null | 4 | HOUR | (3-Bromo-phenyl)-(2,10-dioxa-6-thia-14,16-diaza-tricyclo[9.8.0.013,18]nonadeca-1(11),12,14,16,18-pentaen-17-yl)-amine (21, 17.8 mg, 0.04 mmol) was suspended in MeOH, to which was added a cloudy aqueous solution of oxone (monopersulfate compound) (73 mg, 0.12 mmol) at room temperature. The suspension was stirred and mon... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | c1ncc2cc3c(cc2n1)OCCCSCCCO3 | c1ncc2cc3c(cc2n1)OCCCSCCCO3 | c1ncc2cc3c(cc2n1)OCCCSCCCO3.c1ccccc1 | null | CO | null | 4 | Brc1cccc(Nc2ncnc3cc4c(cc23)OCCCSCCCO4)c1>CO>O=S1(=O)CCCOc2cc3ncnc(Nc4cccc(Br)c4)c3cc2OCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9e262bb65ec44147a7abef9bcbc36b34 | Brc1cccc(Nc2ncnc3cc4c(cc23)OCCOCCOCCO4)c1>>C#Cc1cccc(Nc2ncnc3cc4c(cc23)OCCOCCOCCO4)c1 | C[Si](C)(C)C#C.C([O-])([O-])=O.[K+].[K+].BrC=1C=C(C=CC1)NC=1C=2C=C3C(=CC2N=CN1)OCCOCCOCCO3.BrC=1C=C(C=CC1)NC=1C=2C=C3C(=CC2N=CN1)OCCOCCOCCO3>>C(#C)C=1C=C(C=CC1)NC=1C=2C=C3C(=CC2N=CN1)OCCOCCOCCO3 | Br[c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][n:12][c:13]3[cH:14][c:15]4[c:16]([cH:17][c:18]23)[O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28]4)[cH:29]1>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][n:12][c:13]3[cH:14][c:15]4[c:16]([cH:17][c:18]23)[O:19][CH2:2... | Brc1cccc(Nc2ncnc3cc4c(cc23)OCCOCCOCCO4)c1 | C#Cc1cccc(Nc2ncnc3cc4c(cc23)OCCOCCOCCO4)c1 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I | CN(C)C=O | Functional Group Interconversion | OtherReaction | 95b76df7bbd0ba7aef764b8988925515b3c4e00700642b1df2a075a9fb68bd8a | 3328c8f87c438567981cd74666102f3c9878dcf86df57abda9cd69bae6cfdc49 | c1ccc(Nc2ncnc3cc4c(cc23)OCCOCCOCCO4)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[C;D1;H1:6]#[C:7]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 10.2 | [{"value": 10.2, "product": "C(#C)C=1C=C(C=CC1)NC=1C=2C=C3C(=CC2N=CN1)OCCOCCOCCO3", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (3-Bromo-phenyl)-(7,8,10,11,13,14-hexahydro-6,9,12,15-tetraoxa-1,3-diaza-cyclododeca[b]naphthalen-4-yl)-amine (Compound 10) (10 mg, 0.5 mmol) was dissolved in DMF (10 mL). Tetrakis(triphenylphosphine) palladium (20 mg), trimethylsilylacetylene (70 microliter, 0.65 mmol), potassium carbonate (10 mg) and copper (I) iodid... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ncc2cc3c(cc2n1)OCCOCCOCCO3 | Br- | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I.CN(C)C=O | null | null | Brc1cccc(Nc2ncnc3cc4c(cc23)OCCOCCOCCO4)c1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Cu]I.CN(C)C=O>C#Cc1cccc(Nc2ncnc3cc4c(cc23)OCCOCCOCCO4)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9b3103b72e3147378a37f482c253d6ca | C1OCOCO1.NS(=O)(=O)c1ccc([N+](=O)[O-])cc1>>O=[N+]([O-])c1ccc(S(=O)(=O)N2COCOC2)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)N.O1COCOC1.CS(=O)(=O)O>>N1(COCOC1)S(=O)(=O)C1=CC=C(C=C1)[N+](=O)[O-] | O1[CH2:12][O:13][CH2:14][O:15][CH2:16]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[NH2:11])[cH:17][cH:18]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([S:8](=[O:9])(=[O:10])[N:11]2[CH2:12][O:13][CH2:14][O:15][CH2:16]2)[cH:17][cH:18]1 | C1OCOCO1.NS(=O)(=O)c1ccc([N+](=O)[O-])cc1 | O=[N+]([O-])c1ccc(S(=O)(=O)N2COCOC2)cc1 | null | null | O.C(C)(=O)O | Functional Group Addition | OtherReaction | 000d2d3beb174d5f5006b387f6cc20960337f20dff053547c22014ac58a1f299 | 2b261c617f25c005ceda417aaba7c54cae1bc4064f563010f9e8bc2ae4ff331a | O=S(=O)(c1ccccc1)N1COCOC1 | O1-[CH2;D2;+0:1]-[#8:2]-[C:3]-[#8:4]-[CH2;D2;+0:5]-1.[NH2;D1;+0:6]-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10]>>[O;D1;H0:8]=[#16:7](=[O;D1;H0:9])(-[c:10])-[N;H0;D3;+0:6]1-[CH2;D2;+0:1]-[#8:2]-[C:3]-[#8:4]-[CH2;D2;+0:5]-1 | 35 | [{"value": 35.0, "product": "N1(COCOC1)S(=O)(=O)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.8, "product": "N1(COCOC1)S(=O)(=O)C1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 5 | MINUTE | 4-Nitrobenzenesulphonamide (2.02 g, 10 mmol) was added to a solution of 1,3,5-trioxane (1.96 g, 20 mmol) in acetic acid (5 ml). The mixture was stirred for 5 minutes and methanesulphonic acid (10 ml) was added slowly. The mixture was then stirred at 35° C. for 20 minutes, cooled to 0° C., diluted with water and extract... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Ether.Ether.Ether | Ether.Ether.Tertiary amine | C1OCOCO1 | C1[NH]COCO1 | c1ccccc1.C1[NH]COCO1 | HO- | O.C(C)(=O)O | 0 | 0.083333 | C1OCOCO1.NS(=O)(=O)c1ccc([N+](=O)[O-])cc1>O.C(C)(=O)O>O=[N+]([O-])c1ccc(S(=O)(=O)N2COCOC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cbba29ad300148f0b5dbff015b5c2449 | CCN(CC)CCOc1ccc([N+](=O)[O-])cc1>>CCN(CC)CCOc1ccc(N)cc1 | C(C)N(CCOC1=CC=C(C=C1)[N+](=O)[O-])CC>>C(C)N(CCOC1=CC=C(N)C=C1)CC | O=[N+:13]([O-])[c:12]1[cH:11][cH:10][c:9]([O:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])[cH:15][cH:14]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:14][cH:15]1 | CCN(CC)CCOc1ccc([N+](=O)[O-])cc1 | CCN(CC)CCOc1ccc(N)cc1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 46 | [{"value": 46.0, "product": "C(C)N(CCOC1=CC=C(N)C=C1)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.7, "product": "C(C)N(CCOC1=CC=C(N)C=C1)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A mixture of 4-(2-diethylaminoethoxy)-1-nitrobenzene (Method 10) (1.0 g, 4.2 mmol) and 10% palladium on charcoal catalyst (200 mg) in ethanol (30 ml) was stirred under an atmosphere of hydrogen for 3 hours. The catalyst was removed by filtration through diatomaceous earth and the filter pad was washed with methanol. Th... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].C(C)O | null | 3 | CCN(CC)CCOc1ccc([N+](=O)[O-])cc1>[Pd].C(C)O>CCN(CC)CCOc1ccc(N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-40c029c48eb649dba92432924394188f | CCN(CC)CCCl.O=[N+]([O-])c1ccc([O-])cc1>>CCN(CC)CCOc1ccc([N+](=O)[O-])cc1 | O.[N+](=O)([O-])C1=CC=C([O-])C=C1.[Na+].Cl.C(C)N(CCCl)CC.C([O-])([O-])=O.[K+].[K+]>>C(C)N(CCOC1=CC=C(C=C1)[N+](=O)[O-])CC | Cl[CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5].[O-:8][c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([N+:13](=[O:14])[O-:15])[cH:16][cH:17]1 | CCN(CC)CCCl.O=[N+]([O-])c1ccc([O-])cc1 | CCN(CC)CCOc1ccc([N+](=O)[O-])cc1 | null | null | C=1(C(=CC=CC1)C)C | Heteroatom Alkylation and Arylation | OtherReaction | 3dd6ea90858eede84ece2f60931b760bd509d5f421f2feb2b0fe7a2c006d84f0 | 62c7c72c35b09d63ca1131e6cd8c0b88a31e29901d660456b77319cfd78354c7 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[O-;H0;D1:4]-[c:5](:[c:6]):[c:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 67.1 | [{"value": 52.0, "product": "C(C)N(CCOC1=CC=C(C=C1)[N+](=O)[O-])CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.1, "product": "C(C)N(CCOC1=CC=C(C=C1)[N+](=O)[O-])CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | Water (8 ml) and xylene (35 ml) were added to a mixture of sodium 4-nitrophenoxide (10.5 g, 65 mmol), 2-(diethylamino)ethylchloride hydrochloride (8.6 g, 50 mmol) and potassium carbonate (10.4 g, 75 mmol) and the resulting mixture was heated at reflux for 2 hours. A Dean-Stark apparatus was then fitted and the water wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ether | null | null | c1ccccc1 | Other | C=1(C(=CC=CC1)C)C | null | 18 | CCN(CC)CCCl.O=[N+]([O-])c1ccc([O-])cc1>C=1(C(=CC=CC1)C)C>CCN(CC)CCOc1ccc([N+](=O)[O-])cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1dcb26f6d6184ee3b17c092fca446c72 | BrCC1CO1.O=[N+]([O-])c1ccc(O)cc1>>O=[N+]([O-])c1ccc(OCC2CO2)cc1 | [N+](=O)([O-])C1=CC=C(C=C1)O.C([O-])([O-])=O.[K+].[K+].C(Br)C1CO1>>[N+](=O)([O-])C1=CC=C(OCC2CO2)C=C1 | Br[CH2:9][CH:10]1[CH2:11][O:12]1.[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([OH:8])[cH:13][cH:14]1>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]([O:8][CH2:9][CH:10]2[CH2:11][O:12]2)[cH:13][cH:14]1 | BrCC1CO1.O=[N+]([O-])c1ccc(O)cc1 | O=[N+]([O-])c1ccc(OCC2CO2)cc1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCC2CO2)cc1 | Br-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[OH;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[O;H0;D2;+0:5]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1):[c:8] | 77.7 | [{"value": 77.7, "product": "[N+](=O)([O-])C1=CC=C(OCC2CO2)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | 1-(4-Nitrophenoxy)-2,3-epoxypropane was prepared by an analogous method to that described by Zhen-Zhong Lui et. al. in Synthetic Communications (1994), 24, 833–838. 4-Nitrophenol (4.0 g), anhydrous potassium carbonate (8.0 g) and tetrabutylammonium bromide (0.4 g) were mixed with epibromohydrin (10 ml). The reaction mi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CO1 | HBr | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)OCC | 100 | null | BrCC1CO1.O=[N+]([O-])c1ccc(O)cc1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)OCC>O=[N+]([O-])c1ccc(OCC2CO2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-12f713cbd2b6455fa7fff07a664a3769 | CN.Nc1ccc(S(=O)(=O)F)cc1>>CNS(=O)(=O)c1ccc(N)cc1 | CN.C(C)N(CC)CC.S(=O)(C1=CC=C(C=C1)N)(=O)F>>CNS(=O)(=O)C1=CC=C(N)C=C1 | [CH3:1][NH2:2].F[S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:11][cH:12]1>>[CH3:1][NH:2][S:3](=[O:4])(=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:11][cH:12]1 | CN.Nc1ccc(S(=O)(=O)F)cc1 | CNS(=O)(=O)c1ccc(N)cc1 | null | null | C(C)O | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccccc1 | F-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 78.1 | [{"value": 76.0, "product": "CNS(=O)(=O)C1=CC=C(N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.1, "product": "CNS(=O)(=O)C1=CC=C(N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 18 | HOUR | Methylamine (3 ml of a 33% solution in ethanol) and then triethylamine (0.159 ml, 1.1 mmol) was added to sulphanilyl fluoride (200 mg, 1.1 mmol), and the mixture heated at 80° C. for 6 hours then at ambient temperature for 18 hours. The volatiles were removed by evaporation and the residue azeotroped with toluene to gi... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HF | C(C)O | 80 | 18 | CN.Nc1ccc(S(=O)(=O)F)cc1>C(C)O>CNS(=O)(=O)c1ccc(N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1606dffd93e44b718532834e0f8c1c8d | COCCN.Nc1ccc(S(=O)(=O)F)cc1>>COCCNS(=O)(=O)c1ccc(N)cc1 | COCCN.S(=O)(C1=CC=C(C=C1)N)(=O)F.C(C)N(CC)CC>>COCCNS(=O)(=O)C1=CC=C(N)C=C1 | [CH3:1][O:2][CH2:3][CH2:4][NH2:5].F[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:14][cH:15]1>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][c:12]([NH2:13])[cH:14][cH:15]1 | COCCN.Nc1ccc(S(=O)(=O)F)cc1 | COCCNS(=O)(=O)c1ccc(N)cc1 | null | null | C(CCC)O | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccccc1 | F-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 65.4 | [{"value": 65.0, "product": "COCCNS(=O)(=O)C1=CC=C(N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.4, "product": "COCCNS(=O)(=O)C1=CC=C(N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-methoxyethylamine (859 mg, 11.4 mmol), sulphanilyl fluoride (1.0 g, 5.71 mmol), and triethylamine (1.72 g, 22.9 mmol) in n-butanol (15 ml) was heated at reflux for 18 hours. The mixture was allowed to cool and the volatiles were removed by evaporation. The residue was purified by chromatography eluting w... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HF | C(CCC)O | null | null | COCCN.Nc1ccc(S(=O)(=O)F)cc1>C(CCC)O>COCCNS(=O)(=O)c1ccc(N)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ec2c00ed3ca848f29957ef69ffc7e561 | NCCCn1ccnc1.O=C(Cl)c1ccc(Br)cc1>>O=C(NCCCn1ccnc1)c1ccc(Br)cc1 | NCCCN1C=NC=C1.BrC1=CC=C(C(=O)Cl)C=C1>>BrC1=CC=C(C(=O)NCCCN2C=NC=C2)C=C1 | [NH2:3][CH2:4][CH2:5][CH2:6][n:7]1[cH:8][cH:9][n:10][cH:11]1.Cl[C:2](=[O:1])[c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][CH2:6][n:7]1[cH:8][cH:9][n:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]([Br:16])[cH:17][cH:18]1 | NCCCn1ccnc1.O=C(Cl)c1ccc(Br)cc1 | O=C(NCCCn1ccnc1)c1ccc(Br)cc1 | null | null | C(C)O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCCCn1ccnc1)c1ccccc1 | 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] | null | [] | null | null | 18 | HOUR | 1-(3-Aminopropyl)imidazole (2.39 ml, 0.02 mol) was added to a solution of 4-bromobenzoyl chloride (4.0 g, 0.018 mol) in ethanol (250 ml). The mixture was stirred at ambient temperature for 18 hours. The volatiles were removed by evaporation and the residue was purified by chromatography eluting with hexane/dichlorometh... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1c[nH]cn1.c1ccccc1 | HCl | C(C)O | null | 18 | NCCCn1ccnc1.O=C(Cl)c1ccc(Br)cc1>C(C)O>O=C(NCCCn1ccnc1)c1ccc(Br)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b4541496d65843e8ba39b6459bbb8b7e | COCCN.O=S(=O)(Cl)c1ccc(Cl)cc1Cl>>COCCNS(=O)(=O)c1ccc(Cl)cc1Cl | ClC1=C(C=CC(=C1)Cl)S(=O)(=O)Cl.COCCN>>ClC1=C(C=CC(=C1)Cl)S(NCCOC)(=O)=O | [CH3:1][O:2][CH2:3][CH2:4][NH2:5].Cl[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]1[Cl:16]>>[CH3:1][O:2][CH2:3][CH2:4][NH:5][S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][c:15]1[Cl:16] | COCCN.O=S(=O)(Cl)c1ccc(Cl)cc1Cl | COCCNS(=O)(=O)c1ccc(Cl)cc1Cl | null | null | C(CCC)O | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 2,4-Dichlorobenzenesulphonyl chloride (500 mg 2.1 mmol) and 2-methoxyethylamine (230 mg, 3.1 mmol) in n-butanol (10 ml) was heated at reflux for one hour. The volatiles were removed by evaporation and residue purified by chromatography eluting with hexane/ethyl acetate (50:50) to give the title compound. NMR: 3.04 (t, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | C(CCC)O | null | null | COCCN.O=S(=O)(Cl)c1ccc(Cl)cc1Cl>C(CCC)O>COCCNS(=O)(=O)c1ccc(Cl)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c1cc11ebbe0d4252bbb59040cd5dbc06 | CCCN.O=S(=O)(Cl)c1ccc(Cl)cc1Cl>>CCCNS(=O)(=O)c1ccc(Cl)cc1Cl | ClC1=C(C=CC(=C1)Cl)S(=O)(=O)Cl.C(CC)N>>ClC1=C(C=CC(=C1)Cl)S(NCCC)(=O)=O | [CH3:1][CH2:2][CH2:3][NH2:4].Cl[S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]1[Cl:15]>>[CH3:1][CH2:2][CH2:3][NH:4][S:5](=[O:6])(=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][c:14]1[Cl:15] | CCCN.O=S(=O)(Cl)c1ccc(Cl)cc1Cl | CCCNS(=O)(=O)c1ccc(Cl)cc1Cl | null | null | C(CCC)O | Miscellaneous | Sulfonamide synthesis (Schotten-Baumann) primary amine | a86b0632821e188c0a5dc5a5a2aac298ab3eccaee8a52ba46078c3d5975a290d | 50f8fbf3d327483c3eeff8f6cbd4065e4c7600bb501fbe08958a5c79a0926428 | c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 2,4-Dichlorobenzenesulphonyl chloride (500 mg 2.1 mmol) and 1-propylamine (0.2 ml, 2.4 mmol) in n-butanol (10 ml) was heated at reflux for 48 hours. The volatiles were removed by evaporation and the residue triturated with diethylene ether and the product collected by filtration to give the title compound. NMR: 0.78 (t... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | C(CCC)O | null | null | CCCN.O=S(=O)(Cl)c1ccc(Cl)cc1Cl>C(CCC)O>CCCNS(=O)(=O)c1ccc(Cl)cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e5c80abd908e434e87362660a829fe62 | N#CNC(=O)c1ccccc1.Nc1ccc(S(N)(=O)=O)cc1>>N=C(N)Nc1ccc(S(N)(=O)=O)cc1 | S(=O)(C1=CC=C(C=C1)N)(=O)N.C(C1=CC=CC=C1)(=O)NC#N>>S(N)(=O)(=O)C1=CC=C(C=C1)NC(=N)N | O=C(c1ccccc1)[NH:3][C:2]#[N:1].[NH2:4][c:5]1[cH:6][cH:7][c:8]([S:9]([NH2:10])(=[O:11])=[O:12])[cH:13][cH:14]1>>[NH:1]=[C:2]([NH2:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9]([NH2:10])(=[O:11])=[O:12])[cH:13][cH:14]1 | N#CNC(=O)c1ccccc1.Nc1ccc(S(N)(=O)=O)cc1 | N=C(N)Nc1ccc(S(N)(=O)=O)cc1 | null | null | Cl.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | dd44df42b31bde19fead74620111799f04dd5596f1feefd0c1ccb164c4aa5403 | 7bb7c5606a457b76cd0344df0a1af007033251255efdb0ed5da2ca492488bc21 | c1ccccc1 | O=C(-[NH;D2;+0:1]-[C;H0;D2;+0:2]#[N;H0;D1;+0:3])-c1:c:c:c:c:c:1.[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[NH;D1;+0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | A mixture of sulphanilamide (20 g, 0.166 mol), benzoyl cyanamide (34 g, 0.33 mol) in ethanol (60 ml) and concentrated hydrochloric acid (11 ml) was heated on a steam bath until the solvent had evaporated. Water was added and the mixture heated at reflux for 5 minutes. Sodium hydroxide (14.4 g) was added and the mixture... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Secondary amide.Primary amine | Primary amine.Secondary amine | c1ccccc1 | null | c1ccccc1 | HO- | Cl.C(C)O | null | null | N#CNC(=O)c1ccccc1.Nc1ccc(S(N)(=O)=O)cc1>Cl.C(C)O>N=C(N)Nc1ccc(S(N)(=O)=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-59d1004777cc4d44834ff3f01f0bfc24 | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc2c(c1)OCO2.OCCBr>>N#Cc1c(N)nc(SCCO)c(C#N)c1-c1ccc2c(c1)OCO2 | O.NC1=NC(=C(C(=C1C#N)C1=CC2=C(OCO2)C=C1)C#N)S.BrCCO.C([O-])(O)=O.[Na+]>>NC1=NC(=C(C(=C1C#N)C1=CC2=C(OCO2)C=C1)C#N)SCCO | [N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([SH:8])[c:12]([C:13]#[N:14])[c:15]1-[c:16]1[cH:17][cH:18][c:19]2[c:20]([cH:21]1)[O:22][CH2:23][O:24]2.Br[CH2:9][CH2:10][OH:11]>>[N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([S:8][CH2:9][CH2:10][OH:11])[c:12]([C:13]#[N:14])[c:15]1-[c:16]1[cH:17][cH:18][c:19]2[c:20]([cH:21]1)[O:22][... | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc2c(c1)OCO2.OCCBr | N#Cc1c(N)nc(SCCO)c(C#N)c1-c1ccc2c(c1)OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1cc(-c2ccc3c(c2)OCO3)ccn1 | Br-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[SH;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[O;D1;H1:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8] | null | [] | null | null | null | null | 75 mg (0.19 mmol) of 2-amino-4-(1,3-benzodioxol-5-yl)-6-sulfanyl-3,5-pyridinedicarbonitrile [prepared analogously to Dyachenko et al., Russian Journal of Chemistry 33 (7), 1014–1017 (1997); 34 (4), 557–563 (1998)] and 47 mg (0.38 mmol) of 2-bromoethanol and 63 mg (0.75 mmol) of sodium bicarbonate are stirred in 1 ml of... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccncc1.c1ccc2c(c1)OCO2 | HBr | CN(C)C=O | null | null | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc2c(c1)OCO2.OCCBr>CN(C)C=O>N#Cc1c(N)nc(SCCO)c(C#N)c1-c1ccc2c(c1)OCO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-84b5791973bb4e4b97ae5ec3d0a3b7e3 | BrCc1ccccc1.N#Cc1c(N)nc(S)c(C#N)c1-c1ccc2c(c1)OCCO2>>N#Cc1c(N)nc(SCc2ccccc2)c(C#N)c1-c1ccc2c(c1)OCCO2 | O.NC1=NC(=C(C(=C1C#N)C1=CC2=C(OCCO2)C=C1)C#N)S.C(C1=CC=CC=C1)Br.C([O-])(O)=O.[Na+]>>NC1=NC(=C(C(=C1C#N)C1=CC2=C(OCCO2)C=C1)C#N)SCC1=CC=CC=C1 | Br[CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.[N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([SH:8])[c:16]([C:17]#[N:18])[c:19]1-[c:20]1[cH:21][cH:22][c:23]2[c:24]([cH:25]1)[O:26][CH2:27][CH2:28][O:29]2>>[N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([S:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16]([C:17]#[N... | BrCc1ccccc1.N#Cc1c(N)nc(S)c(C#N)c1-c1ccc2c(c1)OCCO2 | N#Cc1c(N)nc(SCc2ccccc2)c(C#N)c1-c1ccc2c(c1)OCCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | S-alkylation of thiols | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1ccc(CSc2cc(-c3ccc4c(c3)OCCO4)ccn2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[SH;D1;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[S;H0;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]):[c:4] | null | [] | null | null | null | null | 100 mg (0.32 mol) of 2-amino-6-sulfanyl-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-3,5-pyridinedicarbonitrile [prepared analogously to Dyachenko et al., Russian Journal of Chemistry 33 (7), 1014–1017 (1997); 34 (4), 557–563 (1998)], 110 mg (0.64 mmol) of benzyl bromide and 108 mg (1.29 mmol) of sodium bicarbonate are stirred... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccncc1.c1ccccc1.c1ccc2c(c1)OCCO2 | HBr | CN(C)C=O | null | null | BrCc1ccccc1.N#Cc1c(N)nc(S)c(C#N)c1-c1ccc2c(c1)OCCO2>CN(C)C=O>N#Cc1c(N)nc(SCc2ccccc2)c(C#N)c1-c1ccc2c(c1)OCCO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8a06105050574671a0aa48f482262b47 | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc2c(c1)OCC(CO)O2.OCCBr>>N#Cc1c(N)nc(SCCO)c(C#N)c1-c1ccc2c(c1)OCC(CO)O2 | OCCBr.C([O-])(O)=O.[Na+].NC1=NC(=C(C(=C1C#N)C1=CC2=C(OC(CO2)CO)C=C1)C#N)S>>NC1=NC(=C(C(=C1C#N)C1=CC2=C(OC(CO2)CO)C=C1)C#N)SCCO | [N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([SH:8])[c:12]([C:13]#[N:14])[c:15]1-[c:16]1[cH:17][cH:18][c:19]2[c:20]([cH:21]1)[O:22][CH2:23][CH:24]([CH2:25][OH:26])[O:27]2.Br[CH2:9][CH2:10][OH:11]>>[N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7]([S:8][CH2:9][CH2:10][OH:11])[c:12]([C:13]#[N:14])[c:15]1-[c:16]1[cH:17][cH:18][c:19]... | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc2c(c1)OCC(CO)O2.OCCBr | N#Cc1c(N)nc(SCCO)c(C#N)c1-c1ccc2c(c1)OCC(CO)O2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | thioether_nucl_sub | 26df88c6a3f5f203c89584658be4e126cb42994c98a2e16bc812e1036cdae857 | 8b2f52296c3a93039174c980b6042ba15754e04d6892a1284c3a32985220b214 | c1cc(-c2ccc3c(c2)OCCO3)ccn1 | Br-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[SH;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[O;D1;H1:3]-[C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8] | null | [] | null | null | null | null | 30 mg (0.09 mmol) of 2-amino-6-sulfanyl-4-[2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,5-pyridinedicarbonitrile [prepared analogously to Dyachenko et al., Russian Journal of Chemistry 33 (7), 1014–1017 (1997); 34 (4), 557–563 (1998)], 22 mg (0.18 mmol) of 2-hydroxyethyl bromide and 29 mg (0.35 mmol) of sodium... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic thiol | Monosulfide | null | null | c1ccncc1.c1ccc2c(c1)OCCO2 | HBr | CN(C)C=O | null | null | N#Cc1c(N)nc(S)c(C#N)c1-c1ccc2c(c1)OCC(CO)O2.OCCBr>CN(C)C=O>N#Cc1c(N)nc(SCCO)c(C#N)c1-c1ccc2c(c1)OCC(CO)O2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a178a1c686c944a49105cd7cae4ba40a | O=C(O)C(=O)c1cccs1.OC12CCN(CC1)CC2>>O=C(OC12CCN(CC1)CC2)C(=O)c1cccs1 | OC12CCN(CC1)CC2.C(C)N(CC)CC.C(C(=O)Cl)(=O)Cl.O=C(C(=O)O)C=1SC=CC1>>N12CCC(CC1)(CC2)OC(C(C=2SC=CC2)=O)=O | O[C:2](=[O:1])[C:12](=[O:13])[c:14]1[cH:15][cH:16][cH:17][s:18]1.[OH:3][C:4]12[CH2:5][CH2:6][N:7]([CH2:8][CH2:9]1)[CH2:10][CH2:11]2>>[O:1]=[C:2]([O:3][C:4]12[CH2:5][CH2:6][N:7]([CH2:8][CH2:9]1)[CH2:10][CH2:11]2)[C:12](=[O:13])[c:14]1[cH:15][cH:16][cH:17][s:18]1 | O=C(O)C(=O)c1cccs1.OC12CCN(CC1)CC2 | O=C(OC12CCN(CC1)CC2)C(=O)c1cccs1 | null | CN(C=O)C | C(Cl)(Cl)Cl | Protection | Esterification of Carboxylic Acids | e9801f206cb4bb9d460f7386b8384e5e0a802882643ef8bad8c1d049e28011dd | 802e74463aa64b37e080342ce437e7d11cc2ce6490f10646d6092e974faa7430 | O=C(OC12CCN(CC1)CC2)C(=O)c1cccs1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[c:5]:[#16;a:6].[C:7]-[C:8](-[OH;D1;+0:9])(-[C:10])-[C:11]>>[#16;a:6]:[c:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C:8](-[C:7])(-[C:10])-[C:11] | null | [] | null | null | null | null | Oxalyl chloride (1.5 ml, 0.017 mol) was added to a solution of oxothien-2-yl-acetic acid (2.24 g, 0.014 mol) and dimethylformamide (one drop) in 30 ml of chloroform (etanol free) at 01 C. The mixture was stirred and allowed to warm at room temperature. After one hour the solvent was evaporated. The residue was dissolve... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Tertiary alcohol | Ketone.Ester | null | null | c1ccsc1.C1CN2CCC1CC2 | HO- | CN(C=O)C.C(Cl)(Cl)Cl | null | null | O=C(O)C(=O)c1cccs1.OC12CCN(CC1)CC2>CN(C=O)C.C(Cl)(Cl)Cl>O=C(OC12CCN(CC1)CC2)C(=O)c1cccs1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b970c2902fc343c48c131f9e85dd4144 | O=C(O[C@H]1CN2CCC1CC2)C(=O)c1ccco1.[Br][Mg][c]1ccccc1>>O=C(O[C@H]1CN2CCC1CC2)C(O)(c1ccccc1)c1ccco1 | [Cl-].[NH4+].CCOCC.C1(=CC=CC=C1)[Mg]Br.N12C[C@@H](C(CC1)CC2)OC(C(C=2OC=CC2)=O)=O>>N12C[C@@H](C(CC1)CC2)OC(C(C2=CC=CC=C2)(O)C=2OC=CC2)=O | [O:1]=[C:2]([O:3][C@H:4]1[CH2:5][N:6]2[CH2:7][CH2:8][CH:9]1[CH2:10][CH2:11]2)[C:12](=[O:13])[c:20]1[cH:21][cH:22][cH:23][o:24]1.[Br][Mg][c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[O:1]=[C:2]([O:3][C@H:4]1[CH2:5][N:6]2[CH2:7][CH2:8][CH:9]1[CH2:10][CH2:11]2)[C:12]([OH:13])([c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1)[c... | O=C(O[C@H]1CN2CCC1CC2)C(=O)c1ccco1.[Br][Mg][c]1ccccc1 | O=C(O[C@H]1CN2CCC1CC2)C(O)(c1ccccc1)c1ccco1 | null | null | N#N.C1CCOC1 | C-C Coupling | Grignard from ketone to alcohol | db2ad3a505f3141c37847e0af43be1bd81d942fe0a7bc68b74ef6bb430d08ffd | 652461eb0cd30990fcbed359f728e518ea93a58c037f4fc210fcb30d2dae5f8d | O=C(O[C@H]1CN2CCC1CC2)C(c1ccccc1)c1ccco1 | [Br]-[Mg]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[c:12](:[c:13]):[#8;a:14]:[c:15]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C;H0;D4;+0:10](-[OH;D1;+0:11])(-[c:12](:[c:13]):[#8;a:14]:[c:15])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 40 | [{"value": 40.0, "product": "N12C[C@@H](C(CC1)CC2)OC(C(C2=CC=CC=C2)(O)C=2OC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Phenylmagnesium bromide, 0.0057 mol (5.7 ml of a solution 1M in THF), was added to a solution of 1.3 g ( 0.0052 mol) of oxofuran-2-ylacetic acid 1-azabicyclo[2.2.2]oct-3(R)-yl ester (intermediate I-4e-) dissolved in 15 ml of THF, at −701 C in N2 atmosphere. The mixture was stirred at this temperature for 10 minuts, and... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Ketone.Ester | Ester.Tertiary alcohol | c1ccccc1 | c1ccccc1 | c1ccoc1.c1ccccc1.C1CN2CCC1CC2 | Br-.Mg | N#N.C1CCOC1 | null | 1 | O=C(O[C@H]1CN2CCC1CC2)C(=O)c1ccco1.[Br][Mg][c]1ccccc1>N#N.C1CCOC1>O=C(O[C@H]1CN2CCC1CC2)C(O)(c1ccccc1)c1ccco1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-441c2bf571bf4dfa9e5795142f06b44e | O=C(O)C(=O)c1ccco1.O[C@H]1CN2CCC1CC2>>O=C(O[C@H]1CN2CCC1CC2)C(=O)c1ccco1 | N12C[C@@H](C(CC1)CC2)O.C(C(=O)Cl)(=O)Cl.O=C(C(=O)O)C=1OC=CC1>>N12C[C@@H](C(CC1)CC2)OC(C(C=2OC=CC2)=O)=O | O[C:2](=[O:1])[C:12](=[O:13])[c:14]1[cH:15][cH:16][cH:17][o:18]1.[OH:3][C@H:4]1[CH2:5][N:6]2[CH2:7][CH2:8][CH:9]1[CH2:10][CH2:11]2>>[O:1]=[C:2]([O:3][C@H:4]1[CH2:5][N:6]2[CH2:7][CH2:8][CH:9]1[CH2:10][CH2:11]2)[C:12](=[O:13])[c:14]1[cH:15][cH:16][cH:17][o:18]1 | O=C(O)C(=O)c1ccco1.O[C@H]1CN2CCC1CC2 | O=C(O[C@H]1CN2CCC1CC2)C(=O)c1ccco1 | null | CN(C=O)C | C(Cl)(Cl)Cl | Protection | Esterification of Carboxylic Acids | c939a2b456dc028ef9b8da8e67cc8c2d4600899fd167913dc054d843bed73832 | 54434098f814b226cfe1782a0bf08b634994a82fd90bdbb778fb3463efef0433 | O=C(O[C@H]1CN2CCC1CC2)C(=O)c1ccco1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[c:5]:[#8;a:6].[#7:7]-[C:8]-[C:9](-[OH;D1;+0:10])-[C:11]>>[#7:7]-[C:8]-[C:9](-[O;H0;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[c:5]:[#8;a:6])-[C:11] | 52.8 | [{"value": 52.5, "product": "N12C[C@@H](C(CC1)CC2)OC(C(C=2OC=CC2)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.8, "product": "N12C[C@@H](C(CC1)CC2)OC(C(C=2OC=CC2)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | Oxalyl chloride (9.75 ml, 0.112 mol) was added to a solution of oxofuran-2-ylacetic acid (10 g, 0.071 mol) and dimethylformamide (one drop) in 150 ml of chloroform (etanol free) at 01 C. The mixture was stirred and allowed to warm at room temperature. After five hours the solvent was evaporated. The residue was dissolv... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Secondary alcohol | Ketone.Ester | null | null | c1ccoc1.C1CN2CCC1CC2 | HO- | CN(C=O)C.C(Cl)(Cl)Cl | null | 15 | O=C(O)C(=O)c1ccco1.O[C@H]1CN2CCC1CC2>CN(C=O)C.C(Cl)(Cl)Cl>O=C(O[C@H]1CN2CCC1CC2)C(=O)c1ccco1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b1dd4ccd1fb84ffc9c14b89c3030a0e6 | O=C(O)C(=O)c1cccs1.O[C@H]1CN2CCC1CC2>>O=C(O[C@H]1CN2CCC1CC2)C(=O)c1cccs1 | N12C[C@@H](C(CC1)CC2)O.C(C(=O)Cl)(=O)Cl.O=C(C(=O)O)C=1SC=CC1>>N12C[C@@H](C(CC1)CC2)OC(C(C=2SC=CC2)=O)=O | O[C:2](=[O:1])[C:12](=[O:13])[c:14]1[cH:15][cH:16][cH:17][s:18]1.[OH:3][C@H:4]1[CH2:5][N:6]2[CH2:7][CH2:8][CH:9]1[CH2:10][CH2:11]2>>[O:1]=[C:2]([O:3][C@H:4]1[CH2:5][N:6]2[CH2:7][CH2:8][CH:9]1[CH2:10][CH2:11]2)[C:12](=[O:13])[c:14]1[cH:15][cH:16][cH:17][s:18]1 | O=C(O)C(=O)c1cccs1.O[C@H]1CN2CCC1CC2 | O=C(O[C@H]1CN2CCC1CC2)C(=O)c1cccs1 | null | CN(C=O)C | C(Cl)(Cl)Cl | Protection | Esterification of Carboxylic Acids | c939a2b456dc028ef9b8da8e67cc8c2d4600899fd167913dc054d843bed73832 | 54434098f814b226cfe1782a0bf08b634994a82fd90bdbb778fb3463efef0433 | O=C(O[C@H]1CN2CCC1CC2)C(=O)c1cccs1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[c:5]:[#16;a:6].[#7:7]-[C:8]-[C:9](-[OH;D1;+0:10])-[C:11]>>[#16;a:6]:[c:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:10]-[C:9](-[C:11])-[C:8]-[#7:7] | 92.6 | [{"value": 92.6, "product": "N12C[C@@H](C(CC1)CC2)OC(C(C=2SC=CC2)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.5, "product": "N12C[C@@H](C(CC1)CC2)OC(C(C=2SC=CC2)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | Oxalyl chloride (1.34 ml, 0.0154 mol) was added to a solution of oxothien-2-yl-acetic acid (2 g, 0.0128 mol) and dimethylformamide (one drop) in 30 ml of chloroform (etanol free) at 01 C. The mixture was stirred and allowed to warm at room temperature. After one hour the solvent was evaporated. The residue was dissolve... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Secondary alcohol | Ketone.Ester | null | null | c1ccsc1.C1CN2CCC1CC2 | HO- | CN(C=O)C.C(Cl)(Cl)Cl | null | 1.5 | O=C(O)C(=O)c1cccs1.O[C@H]1CN2CCC1CC2>CN(C=O)C.C(Cl)(Cl)Cl>O=C(O[C@H]1CN2CCC1CC2)C(=O)c1cccs1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dbaa94bd32244bae89e10ca244ba911a | COC(=O)[C@H](NC(=O)OC(C)(C)C)[C@H](C)OC>>CO[C@@H](C)[C@@H](NC(=O)OC(C)(C)C)C(=O)O | COC([C@H](NC(=O)OC(C)(C)C)[C@@H](OC)C)=O.[Li+].[OH-]>>C(=O)(OC(C)(C)C)N[C@H]([C@@H](OC)C)C(=O)O | C[O:16][C:14]([C@@H:5]([C@@H:3]([O:2][CH3:1])[CH3:4])[NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:15]>>[CH3:1][O:2][C@@H:3]([CH3:4])[C@@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[C:14](=[O:15])[OH:16] | COC(=O)[C@H](NC(=O)OC(C)(C)C)[C@H](C)OC | CO[C@@H](C)[C@@H](NC(=O)OC(C)(C)C)C(=O)O | null | null | O1CCOCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | null | 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] | 90.1 | [{"value": 90.0, "product": "C(=O)(OC(C)(C)C)N[C@H]([C@@H](OC)C)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.1, "product": "C(=O)(OC(C)(C)C)N[C@H]([C@@H](OC)C)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of N-Boc-O-methyl-D-threonine methyl ester (8.09 mmol) in 1,4-dioxane (10 mL) is added a solution of LiOH (24.3 mmol) in water (20 mL). After stirring for 2–3 h, the solvents are removed in vacuo and the residue partitioned between water and ether. The aqueous layer is acidified with solid citric acid to ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | null | Other | O1CCOCC1.O | null | null | COC(=O)[C@H](NC(=O)OC(C)(C)C)[C@H](C)OC>O1CCOCC1.O>CO[C@@H](C)[C@@H](NC(=O)OC(C)(C)C)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-813543242f5f4c4dab084d52cfa4402d | CN(C)C[C@@H](N)C(=O)N1CCC(C2CCN(C)CC2)CC1.O=C(O)c1cc2ccc(Cl)cc2s1>>CN(C)C[C@@H](NC(=O)c1cc2ccc(Cl)cc2s1)C(=O)N1CCC(C2CCN(C)CC2)CC1.Cl | CN(C[C@@H](N)C(=O)N1CCC(CC1)C1CCN(CC1)C)C.ClC=1C=CC2=C(SC(=C2)C(=O)O)C1>>Cl.ClC=1C=CC2=C(SC(=C2)C(=O)N[C@H](CN(C)C)C(=O)N2CCC(CC2)C2CCN(CC2)C)C1 | [CH3:1][N:2]([CH3:3])[CH2:4][C@@H:5]([NH2:6])[C:19](=[O:20])[N:21]1[CH2:22][CH2:23][CH:24]([CH:25]2[CH2:26][CH2:27][N:28]([CH3:29])[CH2:30][CH2:31]2)[CH2:32][CH2:33]1.O[C:7](=[O:8])[c:9]1[cH:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][c:17]2[s:18]1>>[CH3:1][N:2]([CH3:3])[CH2:4][C@@H:5]([NH:6][C:7](=[O:8])[c:9]1[cH:1... | CN(C)C[C@@H](N)C(=O)N1CCC(C2CCN(C)CC2)CC1.O=C(O)c1cc2ccc(Cl)cc2s1 | CN(C)C[C@@H](NC(=O)c1cc2ccc(Cl)cc2s1)C(=O)N1CCC(C2CCN(C)CC2)CC1.Cl | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCC(=O)N1CCC(C2CCNCC2)CC1)c1cc2ccccc2s1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6].[C:7]-[#7:8](-[C:9](=[O;D1;H0:10])-[C:11](-[C:12])-[NH2;D1;+0:13])-[C:14]>>[C:7]-[#7:8](-[C:9](=[O;D1;H0:10])-[C:11](-[C:12])-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#16;a:5]:[c:6])-[C:14] | null | [] | null | null | null | null | Prepared from 1-[β-dimethylamino-D-alaninyl]-4-(1-methylpiperidin-4-yl)piperidine and 6-chlorobenzo[b]thiophene-2-carboxylic acid using methods substantially equivalent to General Coupling Method 1. The HCl salt is prepared following General Salt Formation Method 1.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2sccc2c1.C1CC[NH]CC1.C1CC[NH]CC1 | null | null | null | null | CN(C)C[C@@H](N)C(=O)N1CCC(C2CCN(C)CC2)CC1.O=C(O)c1cc2ccc(Cl)cc2s1>>CN(C)C[C@@H](NC(=O)c1cc2ccc(Cl)cc2s1)C(=O)N1CCC(C2CCN(C)CC2)CC1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7b3ab442c5d74a1997cdacd358df9401 | C[C@@H](O)[C@@H](N)C(=O)N1CCN(C2CCN(C)CC2)CC1.O=C(O)c1cc2cc(Cl)ccc2[nH]1>>C[C@@H](O)[C@@H](NC(=O)c1cc2cc(Cl)ccc2[nH]1)C(=O)N1CCN(C2CCN(C)CC2)CC1 | Cl.N[C@H]([C@H](O)C)C(=O)N1CCN(CC1)C1CCN(CC1)C.ClC=1C=C2C=C(NC2=CC1)C(=O)O.Cl>>Cl.ClC=1C=C2C=C(NC2=CC1)C(=O)N[C@H]([C@H](O)C)C(=O)N1CCN(CC1)C1CCN(CC1)C | [CH3:1][C@@H:2]([OH:3])[C@@H:4]([NH2:5])[C:18](=[O:19])[N:20]1[CH2:21][CH2:22][N:23]([CH:24]2[CH2:25][CH2:26][N:27]([CH3:28])[CH2:29][CH2:30]2)[CH2:31][CH2:32]1.O[C:6](=[O:7])[c:8]1[cH:9][c:10]2[cH:11][c:12]([Cl:13])[cH:14][cH:15][c:16]2[nH:17]1>>[CH3:1][C@@H:2]([OH:3])[C@@H:4]([NH:5][C:6](=[O:7])[c:8]1[cH:9][c:10]2[cH... | C[C@@H](O)[C@@H](N)C(=O)N1CCN(C2CCN(C)CC2)CC1.O=C(O)c1cc2cc(Cl)ccc2[nH]1 | C[C@@H](O)[C@@H](NC(=O)c1cc2cc(Cl)ccc2[nH]1)C(=O)N1CCN(C2CCN(C)CC2)CC1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCC(=O)N1CCN(C2CCNCC2)CC1)c1cc2ccccc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C:7]-[#7:8](-[C:9](=[O;D1;H0:10])-[C:11](-[C:12])-[NH2;D1;+0:13])-[C:14]>>[C:7]-[#7:8](-[C:9](=[O;D1;H0:10])-[C:11](-[C:12])-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6])-[C:14] | null | [] | null | null | null | null | Prepared from 1-(D-allo-threoninyl)-4-(1-methylpiperidin-4-yl)piperazine hydrochloride and 5-chloroindole-2-carboxylic acid using methods substantially equivalent to General Coupling Method 1. The HCl salt is prepared following Salt Formation Method 1. The final crude product is treated with aqueous 0.2 N HCl and purif... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2[nH]ccc2c1.C1C[NH]CC[NH]1.C1CC[NH]CC1 | HO- | null | null | null | C[C@@H](O)[C@@H](N)C(=O)N1CCN(C2CCN(C)CC2)CC1.O=C(O)c1cc2cc(Cl)ccc2[nH]1>>C[C@@H](O)[C@@H](NC(=O)c1cc2cc(Cl)ccc2[nH]1)C(=O)N1CCN(C2CCN(C)CC2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3b2e1627169841bba8a95cfd46efda70 | CC(C)c1oc(-c2ccccc2Cl)nc1CI.[C-]#N>>CC(C)c1oc(-c2ccccc2Cl)nc1CC#N | [C-]#N.[Na+].ClC1=C(C=CC=C1)C=1OC(=C(N1)CI)C(C)C.O>>ClC1=C(C=CC=C1)C=1OC(=C(N1)CC#N)C(C)C | I[CH2:16][c:15]1[c:4]([CH:2]([CH3:1])[CH3:3])[o:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[Cl:13])[n:14]1.[C-:17]#[N:18]>>[CH3:1][CH:2]([CH3:3])[c:4]1[o:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[Cl:13])[n:14][c:15]1[CH2:16][C:17]#[N:18] | CC(C)c1oc(-c2ccccc2Cl)nc1CI.[C-]#N | CC(C)c1oc(-c2ccccc2Cl)nc1CC#N | null | null | CC(=O)C | C-C Coupling | OtherReaction | 347b040e695b34bb71d78d55beea9c7162795a061d052426f1f803b52c4cbe4d | 1dbefa1fc17e03074aa3f6619987f71dfa9a1cb0d61de142a880cd3f05e4f004 | c1ccc(-c2ncco2)cc1 | I-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C:7].[C-;H0;D1:8]#[N;D1;H0:9]>>[C:7]-[c:6]1:[#8;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[C;H0;D2;+0:8]#[N;D1;H0:9] | 82 | [{"value": 82.0, "product": "ClC1=C(C=CC=C1)C=1OC(=C(N1)CC#N)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8.7, "product": "ClC1=C(C=CC=C1)C=1OC(=C(N1)CC#N)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In acetone (2 mL) was dissolved 2-(2-chlorophenyl)-4-iodomethyl-5-isopropyloxazole (590 mg, 1.63 mmol). Sodium cyanide (88 mg, 1.63 mmol) was added, and the resulting mixture was heated under reflux for 22 hours. The reaction mixture was cooled to room temperature, poured into water, and extracted with ethyl acetate. T... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Nitrile | null | null | c1cocn1.c1ccccc1 | I- | CC(=O)C | null | null | CC(C)c1oc(-c2ccccc2Cl)nc1CI.[C-]#N>CC(=O)C>CC(C)c1oc(-c2ccccc2Cl)nc1CC#N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d60196164a8444fbb56e9ca8a2f88c55 | CC(C)c1oc(-c2ccccc2Cl)nc1CCO.Cc1ccc(S(=O)(=O)Cl)cc1>>Cc1ccc(S(=O)(=O)OCCc2nc(-c3ccccc3Cl)oc2C(C)C)cc1 | Cl.ClC1=C(C=CC=C1)C=1OC(=C(N1)CCO)C(C)C.O.C1(=CC=C(C=C1)S(=O)(=O)Cl)C>>ClC1=C(C=CC=C1)C=1OC(=C(N1)CCOS(=O)(=O)C1=CC=C(C=C1)C)C(C)C | [OH:9][CH2:10][CH2:11][c:12]1[n:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]2[Cl:21])[o:22][c:23]1[CH:24]([CH3:25])[CH3:26].Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:28][cH:27]1)(=[O:7])=[O:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][c:12]2[n:13][c:14](-[c:15]3[cH:16][cH:17][... | CC(C)c1oc(-c2ccccc2Cl)nc1CCO.Cc1ccc(S(=O)(=O)Cl)cc1 | Cc1ccc(S(=O)(=O)OCCc2nc(-c3ccccc3Cl)oc2C(C)C)cc1 | null | null | N1=CC=CC=C1.C(Cl)Cl | Acylation | Formation of Sulfonic Esters | d05d91207659f8fa672c205a316a670adfe2b92492fc9adad2ee3f241e574fb9 | a7748b0f3b0eba3868d0cf03ae67721db046202accaaea9cadb4edbc96ec8768 | O=S(=O)(OCCc1coc(-c2ccccc2)n1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 49 | [{"value": 49.0, "product": "ClC1=C(C=CC=C1)C=1OC(=C(N1)CCOS(=O)(=O)C1=CC=C(C=C1)C)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.0, "product": "ClC1=C(C=CC=C1)C=1OC(=C(N1)CCOS(=O)(=O)C1=CC=C(C=C1)C)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | In a mixture of methylene chloride (1 mL) and pyridine (2 mL) was dissolved 2-[2-(2-chlorophenyl)-5-isopropyloxazol-4-yl]ethanol (159 mg, 0.598 mmol). Under cooling with water, to the solution was added p-toluenesulfonyl chloride (125 mg, 0.658 mmol). The mixture was stirred for 5 hours. The reaction mixture was poured... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol.Sulfonyl halide | Tosylate | null | null | c1ccccc1.c1cocn1.c1ccccc1 | HCl | N1=CC=CC=C1.C(Cl)Cl | null | 5 | CC(C)c1oc(-c2ccccc2Cl)nc1CCO.Cc1ccc(S(=O)(=O)Cl)cc1>N1=CC=CC=C1.C(Cl)Cl>Cc1ccc(S(=O)(=O)OCCc2nc(-c3ccccc3Cl)oc2C(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-591dbc95e67f486b9e9789c5d5d37fd9 | Cc1ccc(S(=O)(=O)OCCc2nc(-c3ccccc3Cl)oc2C(C)C)cc1.[I-]>>CC(C)c1oc(-c2ccccc2Cl)nc1CCI | [I-].[Na+].ClC1=C(C=CC=C1)C=1OC(=C(N1)CCOS(=O)(=O)C1=CC=C(C=C1)C)C(C)C.O>>ClC1=C(C=CC=C1)C=1OC(=C(N1)CCI)C(C)C | Cc1ccc(S(=O)(=O)O[CH2:17][CH2:16][c:15]2[c:4]([CH:2]([CH3:1])[CH3:3])[o:5][c:6](-[c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]3[Cl:13])[n:14]2)cc1.[I-:18]>>[CH3:1][CH:2]([CH3:3])[c:4]1[o:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[Cl:13])[n:14][c:15]1[CH2:16][CH2:17][I:18] | Cc1ccc(S(=O)(=O)OCCc2nc(-c3ccccc3Cl)oc2C(C)C)cc1.[I-] | CC(C)c1oc(-c2ccccc2Cl)nc1CCI | null | null | CC(=O)C | Functional Group Interconversion | OtherReaction | 252212a616714f8874db6269dd7f8dd14d7a8ff04f2ae913f3f8b39c1296a9e4 | 7d4806481a626b7c7f4e5b69bd83274a88a40e4c6a2960dcfa212a4447a3de57 | c1ccc(-c2ncco2)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]-[c:3](:[#7;a:4]):[c:5]:[#8;a:6]):c:c:1.[I-;H0;D0:7]>>[#7;a:4]:[c:3](-[C:2]-[CH2;D2;+0:1]-[I;H0;D1;+0:7]):[c:5]:[#8;a:6] | 96 | [{"value": 96.0, "product": "ClC1=C(C=CC=C1)C=1OC(=C(N1)CCI)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.4, "product": "ClC1=C(C=CC=C1)C=1OC(=C(N1)CCI)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | In acetone (2 mL) was dissolved 2-(2-chlorophenyl)-5-isopropyl-4-[2-(p-toluenesulfonyloxy)ethyl]oxazole (123 mg, 0.293 mmol). To the solution was added sodium iodide (176 mg, 1.17 mmol). The mixture was heated overnight under reflux. The reaction mixture was allowed to reach room temperature, poured into water, and ext... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate | Primary halide | c1ccccc1 | null | c1cocn1.c1ccccc1 | TsOH.HO- | CC(=O)C | null | null | Cc1ccc(S(=O)(=O)OCCc2nc(-c3ccccc3Cl)oc2C(C)C)cc1.[I-]>CC(=O)C>CC(C)c1oc(-c2ccccc2Cl)nc1CCI |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-94ad8cdeae8d45b6af653a0441258466 | COC(=O)c1cc[nH]c1.Clc1ccc2ccccc2n1>>COC(=O)c1ccn(-c2ccc3ccccc3n2)c1 | O.C([O-])([O-])=O.[K+].[K+].COC(=O)C1=CNC=C1.ClC1=NC2=CC=CC=C2C=C1>>COC(=O)C1=CN(C=C1)C1=NC2=CC=CC=C2C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][nH:8][cH:19]1.Cl[c:9]1[cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[n:18]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][n:8](-[c:9]2[cH:10][cH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]3[n:18]2)[cH:19]1 | COC(=O)c1cc[nH]c1.Clc1ccc2ccccc2n1 | COC(=O)c1ccn(-c2ccc3ccccc3n2)c1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 0f41158080bd72518d9a6b2389c4c528ac037a6b5eac12dbe2506d72e4b3d2c9 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2nc(-n3cccc3)ccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[nH;D2;+0:11]:[c:12]:[c:13]:1>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[n;H0;D3;+0:11](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:12]:[c:13]:1 | 65.8 | [{"value": 65.8, "product": "COC(=O)C1=CN(C=C1)C1=NC2=CC=CC=C2C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 23 | HOUR | 1.73 g (12.5 mmol) of potassium carbonate are added at 20° C. under an argon atmosphere to 0.625 g (5 mmol) of 3-methoxycarbonyl-1H-pyrrole and 0.82 g (5 mmol) of 2-chloroquinoline dissolved in 10 mL of dimethyl sulphoxide. After stirring at 100° C. for 23 hours, the reaction mixture is poured into 30 mL of water and i... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1.c1ccc2ncccc2c1 | c1cc[nH]c1.c1ccc2ncccc2c1 | c1cc[nH]c1.c1ccc2ncccc2c1 | HCl | CS(=O)C | 100 | 23 | COC(=O)c1cc[nH]c1.Clc1ccc2ccccc2n1>CS(=O)C>COC(=O)c1ccn(-c2ccc3ccccc3n2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-93014e71c52f43e1976c370c2c3121ae | COC(=O)c1cc[nH]c1.Clc1ccnc2ccccc12>>COC(=O)c1ccn(-c2ccnc3ccccc23)c1 | O.C([O-])([O-])=O.[K+].[K+].COC(=O)C1=CNC=C1.ClC1=CC=NC2=CC=CC=C12>>COC(=O)C1=CN(C=C1)C1=CC=NC2=CC=CC=C12 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][nH:8][cH:19]1.Cl[c:9]1[cH:10][cH:11][n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][n:8](-[c:9]2[cH:10][cH:11][n:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[cH:19]1 | COC(=O)c1cc[nH]c1.Clc1ccnc2ccccc12 | COC(=O)c1ccn(-c2ccnc3ccccc23)c1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 0f41158080bd72518d9a6b2389c4c528ac037a6b5eac12dbe2506d72e4b3d2c9 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2c(-n3cccc3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[nH;D2;+0:14]:[c:15]:[c:16]:1>>[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[n;H0;D3;+0:14](-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:2:[c:8]):[c:15]:[c:16]:1 | 59.5 | [{"value": 59.5, "product": "COC(=O)C1=CN(C=C1)C1=CC=NC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 23 | HOUR | 1.73 g (12.5 mmol) of potassium carbonate are added at 20° C. under an argon atmosphere to 0.625 g (5 mmol) of 3-methoxycarbonyl-1H-pyrrole and 0.82 g (5 mmol) of 4-chloroquinoline dissolved in 10 mL of dimethyl sulphoxide. After stirring at 100° C. for 23 hours, the reaction mixture is poured into 30 mL of water and t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1.c1ccc2ncccc2c1 | c1cc[nH]c1.c1ccc2ncccc2c1 | c1cc[nH]c1.c1ccc2ncccc2c1 | HCl | CS(=O)C | 100 | 23 | COC(=O)c1cc[nH]c1.Clc1ccnc2ccccc12>CS(=O)C>COC(=O)c1ccn(-c2ccnc3ccccc23)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0fdfc446bfd34bf9ba01fbb53c5b1065 | Cc1c(C(=O)O)ccn1-c1ccnc2ccccc12.O=C(Cl)C(=O)Cl>>Cc1c(C(=O)Cl)ccn1-c1ccnc2ccccc12.Cl | C(C(=O)Cl)(=O)Cl.C(=O)(O)C1=C(N(C=C1)C1=CC=NC2=CC=CC=C12)C>>Cl.ClC(=O)C1=C(N(C=C1)C1=CC=NC2=CC=CC=C12)C | O[C:4]([c:3]1[c:2]([CH3:1])[n:9](-[c:10]2[cH:11][cH:12][n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]23)[cH:8][cH:7]1)=[O:5].O=C(C(=O)[Cl:20])[Cl:6]>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[Cl:6])[cH:7][cH:8][n:9]1-[c:10]1[cH:11][cH:12][n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12.[ClH:20] | Cc1c(C(=O)O)ccn1-c1ccnc2ccccc12.O=C(Cl)C(=O)Cl | Cc1c(C(=O)Cl)ccn1-c1ccnc2ccccc12.Cl | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccc2c(-n3cccc3)ccnc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6](-[c:7]):[c:8]:1-[C;D1;H3:9].O=C(-[Cl;H0;D1;+0:10])-C(=O)-[Cl;H0;D1;+0:11]>>[C;D1;H3:9]-[c:8]1:[#7;a:6](-[c:7]):[c:5]:[c:4]:[c:3]:1-[C;H0;D3;+0:1](-[Cl;H0;D1;+0:11])=[O;D1;H0:2].[ClH;D0;+0:10] | 98.9 | [{"value": 98.9, "product": "Cl.ClC(=O)C1=C(N(C=C1)C1=CC=NC2=CC=CC=C12)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 16 | HOUR | 11.8 mL (134.8 mmol) of oxalyl chloride are added at 20° C. under an argon atmosphere to 2.09 g (7.24 mmol) of 3-carboxy-2-methyl-1-(quinol-4-yl)-1H-pyrrole dissolved in 150 mL of dichloromethane. After stirring at 20° C. for 16 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1c[nH]cc1.c1ccc2ncccc2c1 | Other | ClCCl | 20 | 16 | Cc1c(C(=O)O)ccn1-c1ccnc2ccccc12.O=C(Cl)C(=O)Cl>ClCCl>Cc1c(C(=O)Cl)ccn1-c1ccnc2ccccc12.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-116bbc84874e4ba3b9e0c615b3d8c0b2 | CCOC(=O)c1ccn(-c2ccnc3ccccc23)c1C>>Cc1c(C(=O)O)ccn1-c1ccnc2ccccc12 | O.[OH-].[Li+].C(C)OC(=O)C1=C(N(C=C1)C1=CC=NC2=CC=CC=C12)C>>C(=O)(O)C1=C(N(C=C1)C1=CC=NC2=CC=CC=C12)C | CC[O:6][C:4]([c:3]1[c:2]([CH3:1])[n:9](-[c:10]2[cH:11][cH:12][n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]23)[cH:8][cH:7]1)=[O:5]>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[cH:7][cH:8][n:9]1-[c:10]1[cH:11][cH:12][n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12 | CCOC(=O)c1ccn(-c2ccnc3ccccc23)c1C | Cc1c(C(=O)O)ccn1-c1ccnc2ccccc12 | null | null | O1CCCC1.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(-n3cccc3)ccnc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 98.6 | [{"value": 98.6, "product": "C(=O)(O)C1=C(N(C=C1)C1=CC=NC2=CC=CC=C12)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2.226 g (53 mmol) of lithium hydroxide monohydrate, in portions of 0.742 g every 24 hours, are added at 20° C. to 2.48 g (8.4 mmol) of 3-ethoxycarbonyl-2-methyl-1-(quinol-4-yl)-1H-pyrrole dissolved in 75 mL of tetrahydrofuran and 75 mL of water. After stirring at reflux for 72 hours, the reaction mixture is concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1c[nH]cc1.c1ccc2ncccc2c1 | Other | O1CCCC1.O | null | null | CCOC(=O)c1ccn(-c2ccnc3ccccc23)c1C>O1CCCC1.O>Cc1c(C(=O)O)ccn1-c1ccnc2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d88754c9caf5409f8c983d0f3a3e0b16 | CCOC(=O)c1cc[nH]c1C.Clc1ccnc2ccccc12>>CCOC(=O)c1ccn(-c2ccnc3ccccc23)c1C | ClC1=CC=NC2=CC=CC=C12.C(C)OC(=O)C1=C(NC=C1)C.[H-].[Na+]>>C(C)OC(=O)C1=C(N(C=C1)C1=CC=NC2=CC=CC=C12)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][nH:9][c:20]1[CH3:21].Cl[c:10]1[cH:11][cH:12][n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][n:9](-[c:10]2[cH:11][cH:12][n:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]23)[c:20]1[CH3:21] | CCOC(=O)c1cc[nH]c1C.Clc1ccnc2ccccc12 | CCOC(=O)c1ccn(-c2ccnc3ccccc23)c1C | null | [Cu] | O.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 84a7a9e9603cb882bfa9bb185a61e5a07491a2d9b4ffd8cd0caa72c85e51157b | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2c(-n3cccc3)ccnc2c1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[c:14]:[nH;D2;+0:15]:[c:16]:1-[C;D1;H3:17]>>[#8:9]-[C:10](=[O;D1;H0:11])-[c:12]1:[c:13]:[c:14]:[n;H0;D3;+0:15](-[c;H0;D3;+0:1]2:[c:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:2:[c:8]):[c:16]:1-[C;D1;H3:17] | 103.6 | [{"value": 103.6, "product": "C(C)OC(=O)C1=C(N(C=C1)C1=CC=NC2=CC=CC=C12)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 0.2 | HOUR | 2.75 g (17.9 mmol) of 3-ethoxycarbonyl-2-methyl-1H-pyrrole are added at 20° C. under an argon atmosphere to 0.756 g (18.9 mmol) of sodium hydride, at 60% by weight in liquid petroleum jelly, suspended in 12 mL of dimethylformamide. After stirring at 20° C. for 0.2 hour, 0.114 g (1.79 mmol) of copper powder and 2.35 mL ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1.c1ccc2ncccc2c1 | c1c[nH]cc1.c1ccc2ncccc2c1 | c1c[nH]cc1.c1ccc2ncccc2c1 | HCl | [Cu].O.CN(C=O)C | 20 | 0.2 | CCOC(=O)c1cc[nH]c1C.Clc1ccnc2ccccc12>[Cu].O.CN(C=O)C>CCOC(=O)c1ccn(-c2ccnc3ccccc23)c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ac28c993563b4f95b88d0b1c4390b3b0 | Cc1c(C(=O)Cl)ccn1-c1ccc2ccccc2n1.N=C(N)N>>Cc1c(C(=O)NC(=N)N)ccn1-c1ccc2ccccc2n1 | Cl.ClC(=O)C1=C(N(C=C1)C1=NC2=CC=CC=C2C=C1)C.[Na].CO.Cl.NC(=N)N>>Cl.N(C(=N)N)C(=O)C1=C(N(C=C1)C1=NC2=CC=CC=C2C=C1)C | Cl[C:4]([c:3]1[c:2]([CH3:1])[n:12](-[c:13]2[cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[n:22]2)[cH:11][cH:10]1)=[O:5].[NH2:6][C:7](=[NH:8])[NH2:9]>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[NH:6][C:7](=[NH:8])[NH2:9])[cH:10][cH:11][n:12]1-[c:13]1[cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[n:22]1 | Cc1c(C(=O)Cl)ccn1-c1ccc2ccccc2n1.N=C(N)N | Cc1c(C(=O)NC(=N)N)ccn1-c1ccc2ccccc2n1 | null | null | COCCOC | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1ccc2nc(-n3cccc3)ccc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6](-[c:7]:[#7;a:8]):[c:9]:1-[C;D1;H3:10].[N;D1;H1:11]=[C:12](-[N;D1;H2:13])-[NH2;D1;+0:14]>>[#7;a:8]:[c:7]-[#7;a:6]1:[c:5]:[c:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:14]-[C:12](=[N;D1;H1:11])-[N;D1;H2:13]):[c:9]:1-[C;D1;H3:10] | 38.2 | [{"value": 38.2, "product": "Cl.N(C(=N)N)C(=O)C1=C(N(C=C1)C1=NC2=CC=CC=C2C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 0.5 | HOUR | 0.795 g (33.1 mmol) of sodium is added at 20° C. under an argon atmosphere to 30 mL of methanol. After complete dissolution, 2.97 g (31.2 mmol) of guanidine hydrochloride are added. After stirring at 20° C. for 0.5 hour, the reaction mixture is filtered under an argon atmosphere. The filtrate is concentrated to dryness... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1c[nH]cc1.c1ccc2ncccc2c1 | HCl | COCCOC | 20 | 0.5 | Cc1c(C(=O)Cl)ccn1-c1ccc2ccccc2n1.N=C(N)N>COCCOC>Cc1c(C(=O)NC(=N)N)ccn1-c1ccc2ccccc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-52db778ef2ac4a7ab922a2d06b8de288 | Cc1c(C(=O)O)ccn1-c1ccc2ccccc2n1.O=C(Cl)C(=O)Cl>>Cc1c(C(=O)Cl)ccn1-c1ccc2ccccc2n1.Cl | C(C(=O)Cl)(=O)Cl.C(=O)(O)C1=C(N(C=C1)C1=NC2=CC=CC=C2C=C1)C>>Cl.ClC(=O)C1=C(N(C=C1)C1=NC2=CC=CC=C2C=C1)C | O[C:4]([c:3]1[c:2]([CH3:1])[n:9](-[c:10]2[cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[n:19]2)[cH:8][cH:7]1)=[O:5].O=C(C(=O)[Cl:20])[Cl:6]>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[Cl:6])[cH:7][cH:8][n:9]1-[c:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[n:19]1.[ClH:20] | Cc1c(C(=O)O)ccn1-c1ccc2ccccc2n1.O=C(Cl)C(=O)Cl | Cc1c(C(=O)Cl)ccn1-c1ccc2ccccc2n1.Cl | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccc2nc(-n3cccc3)ccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6](-[c:7]:[#7;a:8]):[c:9]:1-[C;D1;H3:10].O=C(-[Cl;H0;D1;+0:11])-C(=O)-[Cl;H0;D1;+0:12]>>[#7;a:8]:[c:7]-[#7;a:6]1:[c:5]:[c:4]:[c:3](-[C;H0;D3;+0:1](-[Cl;H0;D1;+0:12])=[O;D1;H0:2]):[c:9]:1-[C;D1;H3:10].[ClH;D0;+0:11] | 104.2 | [{"value": 104.2, "product": "Cl.ClC(=O)C1=C(N(C=C1)C1=NC2=CC=CC=C2C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 16 | HOUR | 10 mL (114.2 mmol) of oxalyl chloride are added at 20° C. under an argon atmosphere to 1.8 g (6.25 mmol) of 3-carboxy-2-methyl-1-(quinol-2-yl)-1H-pyrrole dissolved in 120 mL of dichloromethane. After stirring at 20° C. for 16 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to giv... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1c[nH]cc1.c1ccc2ncccc2c1 | Other | ClCCl | 20 | 16 | Cc1c(C(=O)O)ccn1-c1ccc2ccccc2n1.O=C(Cl)C(=O)Cl>ClCCl>Cc1c(C(=O)Cl)ccn1-c1ccc2ccccc2n1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2554c89ae0a34a9ea0efbd031f33274b | CCOC(=O)c1ccn(-c2ccc3ccccc3n2)c1C>>Cc1c(C(=O)O)ccn1-c1ccc2ccccc2n1 | O.[OH-].[Li+].C(C)OC(=O)C1=C(N(C=C1)C1=NC2=CC=CC=C2C=C1)C.Cl>>C(=O)(O)C1=C(N(C=C1)C1=NC2=CC=CC=C2C=C1)C | CC[O:6][C:4]([c:3]1[c:2]([CH3:1])[n:9](-[c:10]2[cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[n:19]2)[cH:8][cH:7]1)=[O:5]>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[cH:7][cH:8][n:9]1-[c:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[n:19]1 | CCOC(=O)c1ccn(-c2ccc3ccccc3n2)c1C | Cc1c(C(=O)O)ccn1-c1ccc2ccccc2n1 | null | null | O1CCCC1.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2nc(-n3cccc3)ccc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 111.1 | [{"value": 111.1, "product": "C(=O)(O)C1=C(N(C=C1)C1=NC2=CC=CC=C2C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 3.9 g (93 mmol) of lithium hydroxide monohydrate, portionwise every 24 hours, are added at 20° C. to 1.9 g (6.78 mmol) of 3-ethoxycarbonyl-2-methyl-1-(quinol-2-yl)-1H-pyrrole dissolved in 50 mL of tetrahydrofuran and 50 mL of water. After stirring at reflux for 72 hours, the reaction mixture is concentrated to dryness ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1c[nH]cc1.c1ccc2ncccc2c1 | Other | O1CCCC1.O | null | null | CCOC(=O)c1ccn(-c2ccc3ccccc3n2)c1C>O1CCCC1.O>Cc1c(C(=O)O)ccn1-c1ccc2ccccc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1ab15b1ea8ea4ab3a4f658cb729946cf | CCOC(=O)c1cc[nH]c1C.Clc1ccc2ccccc2n1>>CCOC(=O)c1ccn(-c2ccc3ccccc3n2)c1C | ClC1=NC2=CC=CC=C2C=C1.C(C)OC(=O)C1=C(NC=C1)C.[H-].[Na+]>>C(C)OC(=O)C1=C(N(C=C1)C1=NC2=CC=CC=C2C=C1)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][nH:9][c:20]1[CH3:21].Cl[c:10]1[cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[n:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][n:9](-[c:10]2[cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[n:19]2)[c:20]1[CH3:21] | CCOC(=O)c1cc[nH]c1C.Clc1ccc2ccccc2n1 | CCOC(=O)c1ccn(-c2ccc3ccccc3n2)c1C | null | [Cu] | O.CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 84a7a9e9603cb882bfa9bb185a61e5a07491a2d9b4ffd8cd0caa72c85e51157b | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2nc(-n3cccc3)ccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[c:11]:[nH;D2;+0:12]:[c:13]:1-[C;D1;H3:14]>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[c:11]:[n;H0;D3;+0:12](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5]):[c:13]:1-[C;D1;H3:14] | null | [] | 20 | CELSIUS | 0.2 | HOUR | 2.75 g (17.9 mmol) of 3-ethoxycarbonyl-2-methyl-1H-pyrrole are added at 20° C. under an argon atmosphere to 0.756 g (18.9 mmol) of sodium hydride, at 60% by weight in liquid petroleum jelly, suspended in 12 mL of dimethylformamide. After stirring at 20° C. for 0.2 hour, 0.114 g (1.79 mmol) of copper powder and 2.93 g (... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1.c1ccc2ncccc2c1 | c1c[nH]cc1.c1ccc2ncccc2c1 | c1c[nH]cc1.c1ccc2ncccc2c1 | HCl | [Cu].O.CN(C=O)C | 20 | 0.2 | CCOC(=O)c1cc[nH]c1C.Clc1ccc2ccccc2n1>[Cu].O.CN(C=O)C>CCOC(=O)c1ccn(-c2ccc3ccccc3n2)c1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-312958cfe16b4c57aa0d1e032b302eaf | O=C(Cl)C(=O)Cl.O=C(O)c1ccn(-c2nccc3ccccc23)c1>>Cl.O=C(Cl)c1ccn(-c2nccc3ccccc23)c1 | C(C(=O)Cl)(=O)Cl.C(=O)(O)C1=CN(C=C1)C1=NC=CC2=CC=CC=C12>>Cl.ClC(=O)C1=CN(C=C1)C1=NC=CC2=CC=CC=C12 | O=C(C(=O)[Cl:4])[Cl:1].O[C:3](=[O:2])[c:5]1[cH:6][cH:7][n:8](-[c:9]2[n:10][cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[cH:19]1>>[ClH:1].[O:2]=[C:3]([Cl:4])[c:5]1[cH:6][cH:7][n:8](-[c:9]2[n:10][cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[cH:19]1 | O=C(Cl)C(=O)Cl.O=C(O)c1ccn(-c2nccc3ccccc23)c1 | Cl.O=C(Cl)c1ccn(-c2nccc3ccccc23)c1 | null | null | ClCCl | Functional Group Interconversion | Alcohol to chloride_Other | 013cec2edeb273a7a148f349d36a52d99ff4e7bcf8eed78085df830088e387ac | aedb1f68dc5b7eb0583043e1125b741382b17974140a2f46554f0110e2ddc884 | c1ccc2c(-n3cccc3)nccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6]:[#7;a:7]):[c:8]:[c:9]:1.O=C(-[Cl;H0;D1;+0:10])-C(=O)-[Cl;H0;D1;+0:11]>>[#7;a:7]:[c:6]-[#7;a:5]1:[c:4]:[c:3](-[C;H0;D3;+0:1](-[Cl;H0;D1;+0:11])=[O;D1;H0:2]):[c:9]:[c:8]:1.[ClH;D0;+0:10] | 100.8 | [{"value": 100.8, "product": "Cl.ClC(=O)C1=CN(C=C1)C1=NC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 0.5 | HOUR | 0.4 mL (4.5 mmol) of oxalyl chloride is added at 20° C. under an argon atmosphere to 0.58 g (2.2 mmol) of 3-carboxy-1-(isoquinol-1-yl)-1H-pyrrole dissolved in 45 mL of dichloromethane. After stirring at 20° C. for 0.5 hour, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give 0.65 g ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid | Acyl halide | null | null | c1cc[nH]c1.c1ccc2cnccc2c1 | Other | ClCCl | 20 | 0.5 | O=C(Cl)C(=O)Cl.O=C(O)c1ccn(-c2nccc3ccccc23)c1>ClCCl>Cl.O=C(Cl)c1ccn(-c2nccc3ccccc23)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-96c3dc202bcb4abf93b24b0126811e26 | COC(=O)c1ccn(-c2nccc3ccccc23)c1>>O=C(O)c1ccn(-c2nccc3ccccc23)c1 | O.[OH-].[Li+].COC(=O)C1=CN(C=C1)C1=NC=CC2=CC=CC=C12>>C(=O)(O)C1=CN(C=C1)C1=NC=CC2=CC=CC=C12 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][n:7](-[c:8]2[n:9][cH:10][cH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][n:7](-[c:8]2[n:9][cH:10][cH:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18]1 | COC(=O)c1ccn(-c2nccc3ccccc23)c1 | O=C(O)c1ccn(-c2nccc3ccccc23)c1 | null | null | O1CCCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(-n3cccc3)nccc2c1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 107.7 | [{"value": 107.7, "product": "C(=O)(O)C1=CN(C=C1)C1=NC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.237 g (5.65 mmol) of lithium hydroxide monohydrate is added at 20° C. to 0.57 g (2.26 mmol) of 3-methoxycarbonyl-1-(isoquinol-1-yl)-1H-pyrrole dissolved in 15 mL of tetrahydrofuran and 15 mL of water. After stirring at reflux for 2 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cc[nH]c1.c1ccc2cnccc2c1 | Other | O1CCCC1.O | null | null | COC(=O)c1ccn(-c2nccc3ccccc23)c1>O1CCCC1.O>O=C(O)c1ccn(-c2nccc3ccccc23)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7eea0a2e7ebc4fc99f7138cf5f09a335 | COC(=O)c1cc[nH]c1.Clc1nccc2ccccc12>>COC(=O)c1ccn(-c2nccc3ccccc23)c1 | O.C([O-])([O-])=O.[K+].[K+].COC(=O)C1=CNC=C1.ClC1=NC=CC2=CC=CC=C12>>COC(=O)C1=CN(C=C1)C1=NC=CC2=CC=CC=C12 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][nH:8][cH:19]1.Cl[c:9]1[n:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][n:8](-[c:9]2[n:10][cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[cH:19]1 | COC(=O)c1cc[nH]c1.Clc1nccc2ccccc12 | COC(=O)c1ccn(-c2nccc3ccccc23)c1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 64941681a78379ce7a568f1d8a1309e87b488f1d656284455a26054be1853b83 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2c(-n3cccc3)nccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[c:6].[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]1:[c:11]:[nH;D2;+0:12]:[c:13]:[c:14]:1>>[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]1:[c:11]:[n;H0;D3;+0:12](-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](:[c:5]):[c:6]):[c:13]:[c:14]:1 | 88.5 | [{"value": 88.5, "product": "COC(=O)C1=CN(C=C1)C1=NC=CC2=CC=CC=C12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 22 | HOUR | 1.04 g (7.5 mmol) of potassium carbonate are added at 20° C. under an argon atmosphere to 0.376 g (3 mmol) of 3-methoxycarbonyl-1H-pyrrole and 0.49 g (3 mmol) of 1-chloroisoquinoline dissolved in 6 mL of dimethyl sulphoxide. After stirring at 100° C. for 22 hours, the reaction mixture is poured into 15 mL of water and ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cc[nH]c1.c1ccc2cnccc2c1 | c1cc[nH]c1.c1ccc2cnccc2c1 | c1cc[nH]c1.c1ccc2cnccc2c1 | HCl | CS(=O)C | 100 | 22 | COC(=O)c1cc[nH]c1.Clc1nccc2ccccc12>CS(=O)C>COC(=O)c1ccn(-c2nccc3ccccc23)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3300df1e364043fc82c01144ac6b645b | N=C(N)N.O=C(Cl)c1ccn(-c2cccc3ncccc23)c1>>N=C(N)NC(=O)c1ccn(-c2cccc3ncccc23)c1 | Cl.ClC(=O)C1=CN(C=C1)C1=C2C=CC=NC2=CC=C1.Cl.NC(=N)N.C[O-].[Na+]>>N(C(=N)N)C(=O)C1=CN(C=C1)C1=C2C=CC=NC2=CC=C1 | [NH:1]=[C:2]([NH2:3])[NH2:4].Cl[C:5](=[O:6])[c:7]1[cH:8][cH:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]3[n:16][cH:17][cH:18][cH:19][c:20]23)[cH:21]1>>[NH:1]=[C:2]([NH2:3])[NH:4][C:5](=[O:6])[c:7]1[cH:8][cH:9][n:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]3[n:16][cH:17][cH:18][cH:19][c:20]23)[cH:21]1 | N=C(N)N.O=C(Cl)c1ccn(-c2cccc3ncccc23)c1 | N=C(N)NC(=O)c1ccn(-c2cccc3ncccc23)c1 | null | null | O1CCCC1.ClCCl.CO | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | c1cc(-n2cccc2)c2cccnc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1.[N;D1;H1:9]=[C:10](-[N;D1;H2:11])-[NH2;D1;+0:12]>>[N;D1;H1:9]=[C:10](-[N;D1;H2:11])-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5](-[c:6]):[c:7]:[c:8]:1 | 31.4 | [{"value": 31.4, "product": "N(C(=N)N)C(=O)C1=CN(C=C1)C1=C2C=CC=NC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 22 | CELSIUS | 2 | HOUR | 0.9 g (9.42 mmol) of guanidine hydrochloride is added to a solution of 0.51 g (9.44 mmol) of sodium methoxide in 15 mL of methanol at a temperature in the region of 22° C. under an argon atmosphere. After stirring at a temperature in the region of 22° C. for 2 hours, the solvent is evaporated off under reduced pressure... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cc[nH]c1.c1ccc2ncccc2c1 | HCl | O1CCCC1.ClCCl.CO | 22 | 2 | N=C(N)N.O=C(Cl)c1ccn(-c2cccc3ncccc23)c1>O1CCCC1.ClCCl.CO>N=C(N)NC(=O)c1ccn(-c2cccc3ncccc23)c1 |
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