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-4706a63b928d4b74b43d4d6ac8d84992 | Cc1ccc(C(=O)Cl)cc1.Nc1ccccc1>>Cc1ccc(NC(=O)c2ccccc2)cc1 | ClCCl.NC1=CC=CC=C1.C1(=CC=C(C=C1)C(=O)Cl)C>>CC1=CC=C(NC(C2=CC=CC=C2)=O)C=C1 | Cl[C:7](=[O:8])[c:9]1[cH:4][cH:3][c:2]([CH3:1])[cH:16][cH:14]1.[c:5]1([NH2:6])[cH:10][cH:11][cH:12][cH:13][cH:15]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[cH:15][cH:16]1 | Cc1ccc(C(=O)Cl)cc1.Nc1ccccc1 | Cc1ccc(NC(=O)c2ccccc2)cc1 | null | null | CCOCC | Acylation | OtherReaction | 3f47c8f9e95058222b6f61daaefd3df28ddac7a7e496aca2613ee2819d83f23e | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(Nc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[cH;D2;+0:5]:[c:6](-[C;D1;H3:7]):[c:8]:[cH;D2;+0:9]:1.[NH2;D1;+0:10]-[c;H0;D3;+0:11]1:[cH;D2;+0:12]:[c:13]:[c:14]:[cH;D2;+0:15]:[cH;D2;+0:16]:1>>[C;D1;H3:7]-[c:6]1:[c:8]:[cH;D2;+0:9]:[c;H0;D3;+0:11](-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c;H0;D3;+0:3]2:... | null | [] | null | null | 0.5 | HOUR | To a 0° C. dichloromethane (300 mL) solution of 25 mL (274 mmol) of aniline was added 16 mL (123 mmol) para-toluoyl chloride over 10 min. The mixture was stirred at room temperature for 0.5 h, treated with 200 mL of ether and filtered immediately. The filtrate was washed with 1 M HCl (2×50 mL), 0.1 M NaOH (2×50 mL), an... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | CCOCC | null | 0.5 | Cc1ccc(C(=O)Cl)cc1.Nc1ccccc1>CCOCC>Cc1ccc(NC(=O)c2ccccc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3f973467b88445e8a5090f809444380e | C=CS(C)(=O)=O.COc1ccc(CN(Cc2ccc(OC)cc2)S(=O)(=O)c2ccc(NCc3ccc(C)cc3)cc2)cc1>>COc1ccc(CN(Cc2ccc(OC)cc2)S(=O)(=O)c2ccc(N(CCS(C)(=O)=O)Cc3ccc(C)cc3)cc2)cc1 | CC1=CC=C(CNC2=CC=C(C=C2)S(=O)(=O)N(CC2=CC=C(C=C2)OC)CC2=CC=C(C=C2)OC)C=C1.CS(=O)(=O)C=C.[H-].[Na+]>>CS(=O)(=O)CCN(C1=CC=C(C=C1)S(=O)(=O)N(CC1=CC=C(C=C1)OC)CC1=CC=C(C=C1)OC)CC1=CC=C(C=C1)C | [CH2:26]=[CH:27][S:28]([CH3:29])(=[O:30])=[O:31].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[cH:16][cH:17]2)[S:18](=[O:19])(=[O:20])[c:21]2[cH:22][cH:23][c:24]([NH:25][CH2:32][c:33]3[cH:34][cH:35][c:36]([CH3:37])[cH:38][cH:39]3)[cH:40][cH:41]2)[cH:42][cH:43]1>>[CH... | C=CS(C)(=O)=O.COc1ccc(CN(Cc2ccc(OC)cc2)S(=O)(=O)c2ccc(NCc3ccc(C)cc3)cc2)cc1 | COc1ccc(CN(Cc2ccc(OC)cc2)S(=O)(=O)c2ccc(N(CCS(C)(=O)=O)Cc3ccc(C)cc3)cc2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | aza-Michael addition secondary | 8acf647a588bdc7347506dcd3290904024f41acb450fe55eb6c0af193ad82ab8 | 828fcbb87adfef9f22c9a1e52b43c3df76cb2e49bfe62b57e8b79965772a2bed | O=S(=O)(c1ccc(NCc2ccccc2)cc1)N(Cc1ccccc1)Cc1ccccc1 | [C;D1;H3:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[CH;D2;+0:5]=[CH2;D1;+0:6].[c:7]:[c:8](-[NH;D2;+0:9]-[C:10]-[c:11]):[c:12]>>[C;D1;H3:1]-[#16:2](=[O;D1;H0:3])(=[O;D1;H0:4])-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[N;H0;D3;+0:9](-[C:10]-[c:11])-[c:8](:[c:7]):[c:12] | 75.1 | [{"value": 75.1, "product": "CS(=O)(=O)CCN(C1=CC=C(C=C1)S(=O)(=O)N(CC1=CC=C(C=C1)OC)CC1=CC=C(C=C1)OC)CC1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | 4-[(4-methyl-benzyl)-amino]-[N,N-bis(4-methoxy-benzyl)]-benzenesulfonamide (1.03 g, 2.6 mmol) was dissolved in 6 mL of DMF at room temperature, to which methylvinyl sulfone (0.175 mL, 2.0 mmol) and sodium hydride (95%, 60 mg, 2.4 mmol) were added. The reaction was stirred at room temperature for 1.5 h, partitioned betw... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Vinyl | Tertiary amine | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CN(C)C=O | null | 1.5 | C=CS(C)(=O)=O.COc1ccc(CN(Cc2ccc(OC)cc2)S(=O)(=O)c2ccc(NCc3ccc(C)cc3)cc2)cc1>CN(C)C=O>COc1ccc(CN(Cc2ccc(OC)cc2)S(=O)(=O)c2ccc(N(CCS(C)(=O)=O)Cc3ccc(C)cc3)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-077245168e9a4c2d9bc2b8f2bc81de07 | C[S-].O=[N+]([O-])c1ccc(Br)nc1>>CSc1ccc([N+](=O)[O-])cn1 | BrC1=NC=C(C=C1)[N+](=O)[O-].C[S-].[Na+]>>CSC1=NC=C(C=C1)[N+](=O)[O-] | [CH3:1][S-:2].Br[c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][n:11]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([N+:7](=[O:8])[O-:9])[cH:10][n:11]1 | C[S-].O=[N+]([O-])c1ccc(Br)nc1 | CSc1ccc([N+](=O)[O-])cn1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | a043117f5ac6655ea3d4f71b77392fbb346566d5ecbe0b9ffd7138c05f760a35 | 1813ae14fbd9cacead4dcfaf9efbd2467a19b3e216836766b78aa6647dcfb48a | c1ccncc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[S-;H0;D1:7]>>[C;D1;H3:6]-[S;H0;D2;+0:7]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | 67.4 | [{"value": 67.4, "product": "CSC1=NC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 2.0 g (9.85 mmol) 2-bromo-5-nitropyridine dissolved in 8 mL DMF was added 690 mg (9.85 mmol) of sodium thiomethoxide. The mixture was stirred at room temperature for 1 h, and partitioned between ethyl acetate and water, dried over MgSO4 and concentrated to obtain 1.13 g of 2-methylthio-5-nitro-pyridine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Monosulfide | c1ccncc1 | c1ccncc1 | c1ccncc1 | Br- | CN(C)C=O | null | 1 | C[S-].O=[N+]([O-])c1ccc(Br)nc1>CN(C)C=O>CSc1ccc([N+](=O)[O-])cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f199975ddd8f47c0ab9cb67abdf59a3f | CSc1ccc(N)cn1.O=Cc1ccc(F)cc1>>CSc1ccc(NCc2ccc(F)cc2)cn1 | FC1=CC=C(C=O)C=C1.NC=1C=CC(=NC1)SC.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>CSC1=NC=C(C=C1)NCC1=CC=C(C=C1)F | [CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:16][n:17]1.O=[CH:8][c:9]1[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]2)[cH:16][n:17]1 | CSc1ccc(N)cn1.O=Cc1ccc(F)cc1 | CSc1ccc(NCc2ccc(F)cc2)cn1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CNc2cccnc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10]):[c:4] | 40.3 | [{"value": 40.3, "product": "CSC1=NC=C(C=C1)NCC1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | To 344 μL (3.20 mmol) of 4-fluorobenzaldehyde and 449 mg (3.20 mmol) of 5-amino-2-methylthio-pyridine dissolved in 8 mL dichloromethane was added 1.11 g (5.25 mmol) sodium triacetoxyborohydride. The reaction mixture was stirred at room temperature for 5 h, and partitioned between ethyl acetate and water, dried over MgS... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccncc1.c1ccccc1 | Other | ClCCl | null | 5 | CSc1ccc(N)cn1.O=Cc1ccc(F)cc1>ClCCl>CSc1ccc(NCc2ccc(F)cc2)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e17c250301514e26be8bfcb2abe5b00e | COc1ccccc1C(=O)N(CCSC)c1ccc(S(N)(=O)=O)cc1>>COc1ccccc1CN(CCSC)c1ccc(S(N)(=O)=O)cc1 | B.C1CCOC1.C1CCOC1.CSCCN(C1=CC=C(C=C1)S(=O)(=O)N)C(C1=C(C=CC=C1)OC)=O>>CSCCN(C1=CC=C(C=C1)S(=O)(=O)N)CC1=C(C=CC=C1)OC | O=[C:9]([c:8]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]1)[N:10]([CH2:11][CH2:12][S:13][CH3:14])[c:15]1[cH:16][cH:17][c:18]([S:19]([NH2:20])(=[O:21])=[O:22])[cH:23][cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][N:10]([CH2:11][CH2:12][S:13][CH3:14])[c:15]1[cH:16][cH:17][c:18]([S:19]([NH2:20])(=[O:21]... | COc1ccccc1C(=O)N(CCSC)c1ccc(S(N)(=O)=O)cc1 | COc1ccccc1CN(CCSC)c1ccc(S(N)(=O)=O)cc1 | null | null | C1CCOC1 | Reduction | Reduction of tertiary amides to amines | f74c5a050b269ec4da3871c266f01344b7447381f47cda744f8b1e9c225ae62d | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | c1ccc(CNc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[#7:2](-[C:3])-[c:4])-[c:5](:[c:6]):[c:7]>>[C:3]-[#7:2](-[c:4])-[CH2;D2;+0:1]-[c:5](:[c:6]):[c:7] | 77.4 | [{"value": 77.0, "product": "CSCCN(C1=CC=C(C=C1)S(=O)(=O)N)CC1=C(C=CC=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.4, "product": "CSCCN(C1=CC=C(C=C1)S(=O)(=O)N)CC1=C(C=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of 1 M BH3.THF/THF (6.8 mL, 6.8 mmol) was added to a solution of 4-[(2-methylthio-ethyl)-(2-methoxy-benzoyl)-amino]-benzenesulfonamide (0.51 g, 1.34 mmol) in THF (5 mL). After 18 h, the excess BH3 was quenched by addition of 0.1 M HCl; followed by partitioning the mixture between CH2Cl2 and NaHCO3. The organ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | null | null | c1ccccc1.c1ccccc1 | Other | C1CCOC1 | null | 18 | COc1ccccc1C(=O)N(CCSC)c1ccc(S(N)(=O)=O)cc1>C1CCOC1>COc1ccccc1CN(CCSC)c1ccc(S(N)(=O)=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4505b8678b23482e8a59f5cccef83453 | CC(=O)Cl.CSCCN(C(=O)c1ccc(F)cc1)c1ccc(S(N)(=O)=O)cc1>>CSCCN(C(=O)c1ccc(F)cc1)c1ccc(S(=O)(=O)NC(C)=O)cc1 | CSCCN(C1=CC=C(C=C1)S(=O)(=O)N)C(C1=CC=C(C=C1)F)=O.C(C)(=O)Cl.CCN(CC)CC>>CSCCN(C1=CC=C(C=C1)S(=O)(=O)NC(C)=O)C(C1=CC=C(C=C1)F)=O | Cl[C:23]([CH3:24])=[O:25].[CH3:1][S:2][CH2:3][CH2:4][N:5]([C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1)[c:15]1[cH:16][cH:17][c:18]([S:19](=[O:20])(=[O:21])[NH2:22])[cH:26][cH:27]1>>[CH3:1][S:2][CH2:3][CH2:4][N:5]([C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1)[c:15]1[cH:16][cH:17][c:18](... | CC(=O)Cl.CSCCN(C(=O)c1ccc(F)cc1)c1ccc(S(N)(=O)=O)cc1 | CSCCN(C(=O)c1ccc(F)cc1)c1ccc(S(=O)(=O)NC(C)=O)cc1 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 403eb34e708e50f7077a9da490b1654c837258ce901614ddd1204eb6f2a10a27 | 37dfa12f19cd8cec29206fb8a18b7504935d92bc326a2084e9ef8a13076d3b87 | O=C(Nc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[#16:5](=[O;D1;H0:6])(=[O;D1;H0:7])-[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[#16:5](=[O;D1;H0:6])(=[O;D1;H0:7])-[c:8] | 81 | [{"value": 81.0, "product": "CSCCN(C1=CC=C(C=C1)S(=O)(=O)NC(C)=O)C(C1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.3, "product": "CSCCN(C1=CC=C(C=C1)S(=O)(=O)NC(C)=O)C(C1=CC=C(C=C1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-[(2-methylthio-ethyl)-(4-fluoro-benzoyl)-amino]-benzenesulfonamide (0.32 g, 0.88 mmol), acetyl chloride (0.069 mL, 76 mg, 0.97 mmol), and Et3N (0.13 mL, 97 mg, 0.96 mmol) in CH2Cl2 (9 mL) was heated at reflux for 2 h. After cooling, the mixture was evaporated in vacuo, and the residue was purified by MP... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Sulfonamide | Sulfonamide.Secondary amide | null | null | c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | null | CC(=O)Cl.CSCCN(C(=O)c1ccc(F)cc1)c1ccc(S(N)(=O)=O)cc1>C(Cl)Cl>CSCCN(C(=O)c1ccc(F)cc1)c1ccc(S(=O)(=O)NC(C)=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9ae83228f5ec4410b154a474b8f6e587 | CSCCN(C(=O)c1ccc(F)cc1)c1ccc(S(=O)(=O)NC(C)=O)cc1>>CCNS(=O)(=O)c1ccc(N(CCSC)Cc2ccc(F)cc2)cc1 | B.C1CCOC1.C1CCOC1.CSCCN(C1=CC=C(C=C1)S(=O)(=O)NC(C)=O)C(C1=CC=C(C=C1)F)=O>>CSCCN(C1=CC=C(C=C1)S(=O)(=O)NCC)CC1=CC=C(C=C1)F | O=[C:2]([CH3:1])[NH:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]([N:11]([CH2:12][CH2:13][S:14][CH3:15])[C:16](=O)[c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]2)[cH:24][cH:25]1>>[CH3:1][CH2:2][NH:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]([N:11]([CH2:12][CH2:13][S:14][CH3:15])[CH2:16][c:17]2[cH:18][cH:19][c:... | CSCCN(C(=O)c1ccc(F)cc1)c1ccc(S(=O)(=O)NC(C)=O)cc1 | CCNS(=O)(=O)c1ccc(N(CCSC)Cc2ccc(F)cc2)cc1 | null | null | C1CCOC1 | Reduction | OtherReaction | a24aff1d5e5a239013305029e9d740c6056aa11925242817568cbf9b8ce7d083 | 1e111e1677c741c445104f499dde4d06874c64781551b41f18ee18795c631ec3 | c1ccc(CNc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[#7:2](-[C:3])-[c:4])-[c:5](:[c:6]):[c:7].O=[C;H0;D3;+0:8](-[C;D1;H3:9])-[#7:10]-[#16:11]>>[#16:11]-[#7:10]-[CH2;D2;+0:8]-[C;D1;H3:9].[C:3]-[#7:2](-[c:4])-[CH2;D2;+0:1]-[c:5](:[c:6]):[c:7] | 60.6 | [{"value": 59.0, "product": "CSCCN(C1=CC=C(C=C1)S(=O)(=O)NCC)CC1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.6, "product": "CSCCN(C1=CC=C(C=C1)S(=O)(=O)NCC)CC1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of 1 M BH3.THF/THF (7.0 mL, 7.0 mmol) was added to a stirring solution of 4-[(2-methylthio-ethyl)-(4-fluoro-benzoyl)-amino]-N-acetyl-benzenesulfonamide (0.29 g, 0.69 mmol) in THF (8 mL). After 18 h, the excess BH3 was quenched by addition of 0.1 M HCl; followed by partitioning the mixture between CH2Cl2 and ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Tertiary amide | null | null | null | c1ccccc1.c1ccccc1 | Other | C1CCOC1 | null | 18 | CSCCN(C(=O)c1ccc(F)cc1)c1ccc(S(=O)(=O)NC(C)=O)cc1>C1CCOC1>CCNS(=O)(=O)c1ccc(N(CCSC)Cc2ccc(F)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc91ba7f425e451d989228df5b9a3e76 | CCNS(=O)(=O)c1ccc(N(CCSC)Cc2ccc(F)cc2)cc1>>CCNS(=O)(=O)c1ccc(N(CCS(C)(=O)=O)Cc2ccc(F)cc2)cc1 | OOS(=O)[O-].[K+].CSCCN(C1=CC=C(C=C1)S(=O)(=O)NCC)CC1=CC=C(C=C1)F.O>>CS(=O)(=O)CCN(C1=CC=C(C=C1)S(=O)(=O)NCC)CC1=CC=C(C=C1)F | [CH3:1][CH2:2][NH:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]([N:11]([CH2:12][CH2:13][S:14][CH3:15])[CH2:18][c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[cH:26][cH:27]1>>[CH3:1][CH2:2][NH:3][S:4](=[O:5])(=[O:6])[c:7]1[cH:8][cH:9][c:10]([N:11]([CH2:12][CH2:13][S:14]([CH3:15])(=[O:16])=[O:17])[CH2:18][c:19]2[cH... | CCNS(=O)(=O)c1ccc(N(CCSC)Cc2ccc(F)cc2)cc1 | CCNS(=O)(=O)c1ccc(N(CCS(C)(=O)=O)Cc2ccc(F)cc2)cc1 | null | null | CO | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1ccc(CNc2ccccc2)cc1 | [C:1]-[C:2]-[S;H0;D2;+0:3]-[C;D1;H3:4]>>[C:1]-[C:2]-[S;H0;D4;+0:3](-[C;D1;H3:4])(=[O;D1;H0:5])=[O;D1;H0:6] | 100 | [{"value": 100.0, "product": "CS(=O)(=O)CCN(C1=CC=C(C=C1)S(=O)(=O)NCC)CC1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of Oxone® (0.54 g, 0.88 mmol) in H2O (2 mL) was added to a 0° C. solution of 4-[(2-methylthio-ethyl)-(4-fluoro-benzyl)-amino]-N-ethyl-benzenesulfonamide (0.13 g, 0.34 mmol) in MeOH (8 mL) resulting in an immediate precipitate. After 1 h, the mixture was partitioned between CH2Cl2 and H2O. The aqueous layer w... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1ccccc1.c1ccccc1 | null | CO | null | 1 | CCNS(=O)(=O)c1ccc(N(CCSC)Cc2ccc(F)cc2)cc1>CO>CCNS(=O)(=O)c1ccc(N(CCS(C)(=O)=O)Cc2ccc(F)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-63953ee471764db6b6b59ef0e61ecf7b | COc1cc(CN(CCCS(C)(=O)=O)c2ccc(S(C)(=O)=O)cc2)ccc1F>>CS(=O)(=O)CCCN(Cc1ccc(F)c(O)c1)c1ccc(S(C)(=O)=O)cc1 | FC1=C(C=C(CN(CCCS(=O)(=O)C)C2=CC=C(C=C2)S(=O)(=O)C)C=C1)OC.[I-].[Li+]>>FC1=C(C=C(C=C1)CN(CCCS(=O)(=O)C)C1=CC=C(C=C1)S(=O)(=O)C)O | C[O:16][c:15]1[c:13]([F:14])[cH:12][cH:11][c:10]([CH2:9][N:8]([CH2:7][CH2:6][CH2:5][S:2]([CH3:1])(=[O:3])=[O:4])[c:18]2[cH:19][cH:20][c:21]([S:22]([CH3:23])(=[O:24])=[O:25])[cH:26][cH:27]2)[cH:17]1>>[CH3:1][S:2](=[O:3])(=[O:4])[CH2:5][CH2:6][CH2:7][N:8]([CH2:9][c:10]1[cH:11][cH:12][c:13]([F:14])[c:15]([OH:16])[cH:17]1)... | COc1cc(CN(CCCS(C)(=O)=O)c2ccc(S(C)(=O)=O)cc2)ccc1F | CS(=O)(=O)CCCN(Cc1ccc(F)c(O)c1)c1ccc(S(C)(=O)=O)cc1 | null | null | N1=C(C=C(C=C1C)C)C | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(CNc2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 24.4 | [{"value": 24.4, "product": "FC1=C(C=C(C=C1)CN(CCCS(=O)(=O)C)C1=CC=C(C=C1)S(=O)(=O)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To 694 mg (1.67 mmol) of (4-fluoro-3-methoxy-benzyl)-(4-methanesulfonyl-phenyl)-(3-methanesulfonyl-propyl)-amine, prepared following the method of Example 5 but replacing 3-pyridinecarboxaldehyde with 4-fluoro-3-methoxybenxaldehyde, dissolved in 3 mL of 2,4,6-collidine was added 402 mg (3.01 mmol) lithium iodide. The m... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1 | Other | N1=C(C=C(C=C1C)C)C | null | null | COc1cc(CN(CCCS(C)(=O)=O)c2ccc(S(C)(=O)=O)cc2)ccc1F>N1=C(C=C(C=C1C)C)C>CS(=O)(=O)CCCN(Cc1ccc(F)c(O)c1)c1ccc(S(C)(=O)=O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b05e5be89b384b4d9231d6e40f8e8eac | CCOc1ccc(C=O)cc1.CSc1ccc(N)cc1>>CCOc1ccc(CNc2ccc(SC)cc2)cc1 | CSC1=CC=C(N)C=C1.C(C)OC1=CC=C(C=O)C=C1.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]>>C(C)OC1=CC=C(CNC2=CC=C(C=C2)SC)C=C1 | O=[CH:8][c:7]1[cH:6][cH:5][c:4]([O:3][CH2:2][CH3:1])[cH:19][cH:18]1.[NH2:9][c:10]1[cH:11][cH:12][c:13]([S:14][CH3:15])[cH:16][cH:17]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][NH:9][c:10]2[cH:11][cH:12][c:13]([S:14][CH3:15])[cH:16][cH:17]2)[cH:18][cH:19]1 | CCOc1ccc(C=O)cc1.CSc1ccc(N)cc1 | CCOc1ccc(CNc2ccc(SC)cc2)cc1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(CNc2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:7]:[c:6](-[NH;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:8] | 71.6 | [{"value": 71.6, "product": "C(C)OC1=CC=C(CNC2=CC=C(C=C2)SC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To 5.0 mL (40.19 mmol) of 4-(methylthio)aniline dissloved in 25 mL dichloromethane was added 5.59 mL (40.19 mmol) 4-ethoxybenzaldehyde followed by 12.78 g (60.28 mmol) sodium triacetoxyborohydride. The mixture was stirred at overnight at room temperature, partitioned between EtOAc and brine, dried over MgSO4 and concen... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | ClCCl | null | 8 | CCOc1ccc(C=O)cc1.CSc1ccc(N)cc1>ClCCl>CCOc1ccc(CNc2ccc(SC)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b33edf77ccf241e9a56e7b20cf2ad78e | CCOc1ccc(CN(Cc2ccsc2)c2ccc(SC)cc2)cc1>>CCOc1ccc(CN(Cc2ccsc2)c2ccc(S(C)(=O)=O)cc2)cc1 | C(C)OC1=CC=C(CN(CC2=CSC=C2)C2=CC=C(C=C2)SC)C=C1.CO.OOS(=O)[O-].[K+].O>>C(C)OC1=CC=C(CN(CC2=CSC=C2)C2=CC=C(C=C2)S(=O)(=O)C)C=C1 | [CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][s:14][cH:15]2)[c:16]2[cH:17][cH:18][c:19]([S:20][CH3:21])[cH:24][cH:25]2)[cH:26][cH:27]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][s:14][cH:15]2)[c:16]2[cH:17][cH:18][c:19]([S:20]([CH3:21])... | CCOc1ccc(CN(Cc2ccsc2)c2ccc(SC)cc2)cc1 | CCOc1ccc(CN(Cc2ccsc2)c2ccc(S(C)(=O)=O)cc2)cc1 | null | null | null | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1ccc(CN(Cc2ccsc2)c2ccccc2)cc1 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[C;D1;H3:1]-[S;H0;D4;+0:2](=[O;D1;H0:6])(=[O;D1;H0:7])-[c:3](:[c:4]):[c:5] | 92 | [{"value": 92.0, "product": "C(C)OC1=CC=C(CN(CC2=CSC=C2)C2=CC=C(C=C2)S(=O)(=O)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To 241 mg (0.652 mmol) of (4-Ethoxy-benzyl)-(4-methylsulfanyl-phenyl)-thiophen-3-ylmethyl-amine dissolved in 6 mL methanol was added 800 mg (1.3 mmol) OXONE™ followed by 600 μL water. The mixture was stirred at room temperature for 2 h, then partitioned between EtOAc and water, adding 1 N NaOH until the aqueous phase w... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1ccccc1.c1ccsc1.c1ccccc1 | null | null | null | 2 | CCOc1ccc(CN(Cc2ccsc2)c2ccc(SC)cc2)cc1>>CCOc1ccc(CN(Cc2ccsc2)c2ccc(S(C)(=O)=O)cc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c227882dcc304196ab72380614cebcb0 | CC([O-])=S.CCOC(=O)[C@H](CCc1ccccc1)NC(=O)C1(NC(=O)[C@H](Br)C2CCOCC2)CCCC1>>CCOC(=O)[C@H](CCc1ccccc1)NC(=O)C1(NC(=O)[C@@H](SC(C)=O)C2CCOCC2)CCCC1 | C(C)(=S)[O-].[K+].C(C)OC([C@@H](NC(=O)C1(CCCC1)NC([C@@H](C1CCOCC1)Br)=O)CCC1=CC=CC=C1)=O>>C(C)OC([C@@H](NC(=O)C1(CCCC1)NC([C@H](C1CCOCC1)SC(C)=O)=O)CCC1=CC=CC=C1)=O | [S:23]=[C:24]([CH3:25])[O-:26].Br[C@@H:22]([C:20]([NH:19][C:18]1([C:16]([NH:15][C@H:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)=[O:17])[CH2:33][CH2:34][CH2:35][CH2:36]1)=[O:21])[CH:27]1[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@H:6]([CH2... | CC([O-])=S.CCOC(=O)[C@H](CCc1ccccc1)NC(=O)C1(NC(=O)[C@H](Br)C2CCOCC2)CCCC1 | CCOC(=O)[C@H](CCc1ccccc1)NC(=O)C1(NC(=O)[C@@H](SC(C)=O)C2CCOCC2)CCCC1 | null | null | O1CCCC1.C(C)(=O)OCC | Acylation | OtherReaction | fb0feb458ec3ce58113f846e0298c71e9283e4a1a2049c2d3d2f75d227413bf4 | 86068a19cdf3a43185421f62a7479868adb1c4df5f522b8ab7be3cab26d60d11 | O=C(CC1CCOCC1)NC1(C(=O)NCCCc2ccccc2)CCCC1 | Br-[C@@H;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#7:4]-[C:5]-[C:6](-[#7:7])=[O;D1;H0:8])-[C:9](-[C:10])-[C:11].[C;D1;H3:12]-[C;H0;D3;+0:13](-[O-;H0;D1:14])=[S;H0;D1;+0:15]>>[#7:7]-[C:6](=[O;D1;H0:8])-[C:5]-[#7:4]-[C:2](=[O;D1;H0:3])-[C@@H;D3;+0:1](-[S;H0;D2;+0:15]-[C;H0;D3;+0:13](-[C;D1;H3:12])=[O;H0;D1;+0:14])-[C:9](-[C:10])-[... | null | [] | null | null | 4 | HOUR | A mixture of potassium thioacetate (1.66 g, 14.6 mmol) and N-[1-[(R)-2-bromo-2-(4-tetrahydropyranyl)acetylamino]-cyclopentanecarbonyl]-L-homophenylalanine ethyl ester (1.84 g, 3.52 mmol) in 50 mL of tetrahydrofuran is stirred at room temperature for 4 hours. The mixture is diluted with ethyl acetate, washed with water,... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Thiocarbonyl | Carbo-thioester | null | null | c1ccccc1.C1CCOCC1.C1CCCC1 | Br- | O1CCCC1.C(C)(=O)OCC | null | 4 | CC([O-])=S.CCOC(=O)[C@H](CCc1ccccc1)NC(=O)C1(NC(=O)[C@H](Br)C2CCOCC2)CCCC1>O1CCCC1.C(C)(=O)OCC>CCOC(=O)[C@H](CCc1ccccc1)NC(=O)C1(NC(=O)[C@@H](SC(C)=O)C2CCOCC2)CCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9c82313f2b26441a97fe05b17f01ced8 | CCO.N[C@@H](CCc1ccccc1)C(=O)O>>CCOC(=O)[C@@H](N)CCc1ccccc1 | Cl.N[C@@H](CCC1=CC=CC=C1)C(=O)O.C(C)O>>Cl.C(C)OC([C@@H](N)CCC1=CC=CC=C1)=O | [CH3:1][CH2:2][OH:3].O[C:4](=[O:5])[C@@H:6]([NH2:7])[CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]([NH2:7])[CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | CCO.N[C@@H](CCc1ccccc1)C(=O)O | CCOC(=O)[C@@H](N)CCc1ccccc1 | null | null | null | Protection | Esterification of Carboxylic Acids | 070670f68a20c1021da94fabee54def4688122fb721af5f52cd5a03630845d0e | 0d8a72b7375d91aa7263e766e03a3cb7c4fa91e27abcd590409ff03b98eed690 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[N;D1;H2:5].[C;D1;H3:6]-[C:7]-[OH;D1;+0:8]>>[C:4]-[C:3](-[N;D1;H2:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-[C:7]-[C;D1;H3:6] | null | [] | null | null | 16 | HOUR | Hydrogen chloride gas is bubbled through a solution of (L)-homophenylalanine (5.13 g, 28.7 mmol) in 100 mL of ethanol for 5 minutes. The mixture is stirred at room temperature for 16 hours. The mixture is concentrated in vacuo to yield L-homophenylalanine ethyl ester hydrochloride as a white solid.
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1 | HO- | null | null | 16 | CCO.N[C@@H](CCc1ccccc1)C(=O)O>>CCOC(=O)[C@@H](N)CCc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47bf0c68953640b1a2190ebcddf47f03 | c1ccc2nc3c(cc2c1)CCC3>>c1ccc2c(c1)C[C@@H]1CCC[C@H]1N2 | C1CCC2=NC=3C=CC=CC3C=C21.[H][H]>>C1CC[C@H]2NC=3C=CC=CC3C[C@@H]21 | [cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[cH:7][c:8]1[c:12]([n:13]2)[CH2:11][CH2:10][CH2:9]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[CH2:7][C@@H:8]1[CH2:9][CH2:10][CH2:11][C@H:12]1[NH:13]2 | c1ccc2nc3c(cc2c1)CCC3 | c1ccc2c(c1)C[C@@H]1CCC[C@H]1N2 | null | O=[Pt]=O | CO | Reduction | OtherReaction | d198e2a306b3860afc00d685bb110b015644bf92b4ed96edf5adaaf981388172 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | c1ccc2c(c1)C[C@@H]1CCC[C@H]1N2 | [c:1]:[c:2]1:[n;H0;D2;+0:3]:[c;H0;D3;+0:4]2:[c;H0;D3;+0:5](:[cH;D2;+0:6]:[c:7]:1:[c:8])-[C:9]-[C:10]-[C:11]-2>>[c:1]:[c:2]1:[c:7](:[c:8])-[CH2;D2;+0:6]-[C@@H;D3;+0:5]2-[C:9]-[C:10]-[C:11]-[C@H;D3;+0:4]-2-[NH;D2;+0:3]-1 | 75 | [{"value": 75.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared by catalytic hydrogenation of 2,3-dihydro-1H-cyclopenta[b]quinoline (0.5 g, 2.43 mmol) in the presence of PtO2 and hydrogen (45 psi) in methanol (50 ml) to give the cis and trans isomers. Separation by flash chromatography (10–30% ethyl acetate/petroleum ether) gave the title compounds a... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccc2nc3c(cc2c1)CCC3 | c1ccc2c(c1)C[C@@H]1CCC[C@H]1N2 | c1ccc2c(c1)C[C@@H]1CCC[C@H]1N2 | null | O=[Pt]=O.CO | null | null | c1ccc2nc3c(cc2c1)CCC3>O=[Pt]=O.CO>c1ccc2c(c1)C[C@@H]1CCC[C@H]1N2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fde3681bcdbb4c189e247c37b32a2948 | CCO.N#CCN1c2ccccc2C[C@H]2CCC[C@H]21>>NCCN1c2ccccc2C[C@@H]2CCC[C@H]21.[NH4+].[OH-] | C1CC[C@H]2N(C=3C=CC=CC3C[C@H]21)CC#N.[H][H].C(C)O>>[OH-].[NH4+].C1CC[C@H]2N(C=3C=CC=CC3C[C@@H]21)CCN | CC[OH:18].[N:1]#[C:2][CH2:3][N:4]1[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH2:11][C@H:12]2[CH2:13][CH2:14][CH2:15][C@@H:16]12>>[NH2:1][CH2:2][CH2:3][N:4]1[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH2:11][C@@H:12]2[CH2:13][CH2:14][CH2:15][C@@H:16]12.[NH4+:17].[OH-:18] | CCO.N#CCN1c2ccccc2C[C@H]2CCC[C@H]21 | NCCN1c2ccccc2C[C@@H]2CCC[C@H]21.[NH4+].[OH-] | null | [Rh] | null | Miscellaneous | OtherReaction | c5fe930315fc955c57267f34a33e3c0f5123b23688eb330cde03f6db4f0bb879 | 66fb8f0dd75af5e83299590e765d125a1b065e4e78f081ffcb92eef4d11421d4 | c1ccc2c(c1)C[C@@H]1CCC[C@H]1N2 | C-C-[OH;D1;+0:1].[#7:2]-[C:3]-[C;H0;D2;+0:4]#[N;H0;D1;+0:5]>>[#7:2]-[C:3]-[CH2;D2;+0:4]-[NH2;D1;+0:5].[OH-;D0:1] | null | [] | null | null | null | null | Catalytic hydrogenation of Cis(1,2,3,3a,9,9a-Hexahydro-cyclopenta[b]quinolin-4-yl)-acetonitrile (0.23 g, 1.08 mmol) in the presence of 5% Rh on Alumina and hydrogen (45 psi) in a 1:1 mixture of ethanol : ammonium hydroxide (40 ml) afforded the title compound. The reaction mixture was filtered through celite concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary alcohol | Primary amine | null | null | c1ccc2c(c1)C[C@@H]1CCC[C@H]1[NH]2 | Other | [Rh] | null | null | CCO.N#CCN1c2ccccc2C[C@H]2CCC[C@H]21>[Rh]>NCCN1c2ccccc2C[C@@H]2CCC[C@H]21.[NH4+].[OH-] |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-095e3ffa08bd49d9aef030a37ce27fc7 | C=O.NCCN1c2ccccc2C[C@H]2CCC[C@H]21>>c1cc2c3c(c1)C[C@@H]1CCC[C@H]1N3CCNC2 | C1CC[C@H]2N(C=3C=CC=CC3C[C@H]21)CCN.C=O.C(=O)(C(F)(F)F)O>>C1CNCC=2C=CC=C3C[C@H]4[C@H](N1C23)CCC4 | O=[CH2:17].[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[CH2:7][C@H:8]1[CH2:9][CH2:10][CH2:11][C@H:12]1[N:13]2[CH2:14][CH2:15][NH2:16]>>[cH:1]1[cH:2][c:3]2[c:4]3[c:5]([cH:6]1)[CH2:7][C@@H:8]1[CH2:9][CH2:10][CH2:11][C@H:12]1[N:13]3[CH2:14][CH2:15][NH:16][CH2:17]2 | C=O.NCCN1c2ccccc2C[C@H]2CCC[C@H]21 | c1cc2c3c(c1)C[C@@H]1CCC[C@H]1N3CCNC2 | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | 96587ac55881be747bdb82c9da30514c6e3c77d7569f41d466b50e8728e0863c | cf32f1267c674fd84d46b8a676a46bd4e3a018dea282d34ea9ab93d79b66d0ee | c1cc2c3c(c1)C[C@@H]1CCC[C@H]1N3CCNC2 | O=[CH2;D1;+0:1].[C:2]-[#7:3](-[C:4]-[C:5]-[NH2;D1;+0:6])-[c:7](:[c:8]):[cH;D2;+0:9]:[c:10]:[c:11]>>[C:2]-[#7:3]1-[C:4]-[C:5]-[NH;D2;+0:6]-[CH2;D2;+0:1]-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:7]-1:[c:8] | null | [] | null | null | null | null | A flask containing Cis 2-(1,2,3,3a,9,9a-Hexahydro-cyclopenta[b]quinolin-4-yl)-ethylamine (0.18 g, 0.84 mmol) and 0.07 ml of 37% aqueous formaldehyde in 2 ml of EtOH was treated with TFA (0.07 mL, 0.92 mmol) at room temperature for 1 hr. The mixture was concentrated under reduced pressure, and the residue was taken up i... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Secondary amine | c1ccc2c(c1)C[C@H]1CCC[C@H]1[NH]2 | c1cc2c3c(c1)C[C@@H]1CCC[C@H]1N3CCNC2 | c1cc2c3c(c1)C[C@@H]1CCC[C@H]1N3CCNC2 | HO- | CCO | null | null | C=O.NCCN1c2ccccc2C[C@H]2CCC[C@H]21>CCO>c1cc2c3c(c1)C[C@@H]1CCC[C@H]1N3CCNC2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bd9fb46e6114406580b1bd0760b0f37d | c1ccc2c(c1)C[C@@H]1CCC[C@H]1N2.c1ccc2c(c1)C[C@H]1CCCC[C@@H]1N2>>N#CCN1c2ccccc2C[C@H]2CCCC[C@@H]21 | C1CCC[C@@H]2NC3=CC=CC=C3C[C@@H]12.C1CC[C@H]2NC=3C=CC=CC3C[C@@H]21>>C1CCC[C@@H]2N(C3=CC=CC=C3C[C@@H]12)CC#N | c1ccc2c(c1)C[C@@H]1CC[CH2:3][C@H:2]1[NH:1]2.[NH:4]1[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH2:11][C@H:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C@H:17]12>>[N:1]#[C:2][CH2:3][N:4]1[c:5]2[cH:6][cH:7][cH:8][cH:9][c:10]2[CH2:11][C@H:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C@H:17]12 | c1ccc2c(c1)C[C@@H]1CCC[C@H]1N2.c1ccc2c(c1)C[C@H]1CCCC[C@@H]1N2 | N#CCN1c2ccccc2C[C@H]2CCCC[C@@H]21 | null | null | null | Functional Group Interconversion | OtherReaction | 06906ed4d211b28f02ae483b468df1ed4d180de9a8d1fa04960538dfdc86b148 | 7608d422aea9a8ef8ae3c2f714ff6df2bbd5cd3e18c44554b52ef4c7b6e0b232 | c1ccc2c(c1)C[C@H]1CCCC[C@@H]1N2 | C1-C-[C@H]2-C-c3:c:c:c:c:c:3-[NH;D2;+0:1]-[C@@H;D3;+0:2]-2-[CH2;D2;+0:3]-1.[C:4]-[C:5](-[C:6])-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[C:4]-[C:5](-[C:6])-[N;H0;D3;+0:7](-[CH2;D2;+0:3]-[C;H0;D2;+0:2]#[N;H0;D1;+0:1])-[c:8](:[c:9]):[c:10] | null | [] | null | null | null | null | The title compounds were prepared according to the procedure of Example 1 step 3 except that Cis and Trans-1,2,3,4,4a,9,9a,10-octahydroacridine were used instead of Cis and Trans 2,3,3a,4,9,9a-Hexahydro-1H-cyclopenta[b]quinoline, respectively.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Secondary amine | Nitrile.Tertiary amine | c1ccc2c(c1)C[C@@H]1CCC[C@H]1N2.c1ccc2c(c1)C[C@H]1CCCC[C@@H]1N2 | c1ccc2c(c1)C[C@H]1CCCC[C@@H]1[NH]2 | c1ccc2c(c1)C[C@H]1CCCC[C@@H]1[NH]2 | Other | null | null | null | c1ccc2c(c1)C[C@@H]1CCC[C@H]1N2.c1ccc2c(c1)C[C@H]1CCCC[C@@H]1N2>>N#CCN1c2ccccc2C[C@H]2CCCC[C@@H]21 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c4100c0093a84bf496380d35ba6f64ed | Clc1nccnc1Cl.OCCOc1ccccc1>>Clc1nccnc1OCCOc1ccccc1 | O([Na])C(C)(C)C.ClC1=NC=CN=C1Cl.O(C1=CC=CC=C1)CCO>>ClC1=NC=CN=C1OCCOC1=CC=CC=C1 | Cl[c:7]1[c:2]([Cl:1])[n:3][cH:4][cH:5][n:6]1.[OH:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[Cl:1][c:2]1[n:3][cH:4][cH:5][n:6][c:7]1[O:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | Clc1nccnc1Cl.OCCOc1ccccc1 | Clc1nccnc1OCCOc1ccccc1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8088ac3623a2ee47f375f73ca665bec9cf80b1384463e6e2f03125aecbcea517 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(OCCOc2cnccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7] | 62 | [{"value": 62.0, "product": "ClC1=NC=CN=C1OCCOC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.9, "product": "ClC1=NC=CN=C1OCCOC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | NaO-t-Bu (2.91 g, 30.29 mmol) was added to a mixture of 2,3-dichloropyrazine (4.75 g, 31.9 mmol) and 2-phenoxyethanol (4.18 g, 30.3 mmol) in dioxane (25 mL). The reaction mixture was stirred at ambient temperature for 1.5 h and then filtered. The filtrate was concentrated under reduced pressure and the crystalline resi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cnccn1 | c1cnccn1 | c1cnccn1.c1ccccc1 | HCl | O1CCOCC1 | null | 1.5 | Clc1nccnc1Cl.OCCOc1ccccc1>O1CCOCC1>Clc1nccnc1OCCOc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3bd268dde30845da893f02ab3b29a6d4 | Clc1nc2ccccc2nc1Cl.OCCOc1ccccc1>>Clc1nc2ccccc2nc1OCCOc1ccccc1 | O(C1=CC=CC=C1)CCO.ClC1=NC2=CC=CC=C2N=C1Cl.O([K])C(C)(C)C>>ClC1=NC2=CC=CC=C2N=C1OCCOC1=CC=CC=C1 | Cl[c:11]1[c:2]([Cl:1])[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[n:10]1.[OH:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[Cl:1][c:2]1[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[n:10][c:11]1[O:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1 | Clc1nc2ccccc2nc1Cl.OCCOc1ccccc1 | Clc1nc2ccccc2nc1OCCOc1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 76f684f6591b23c199df9d989c265ce73ff618d868cc26b6ec9cabfd7980b054 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(OCCOc2cnc3ccccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7] | null | [] | null | null | null | null | The title compound was prepared according to the procedure described in Example 1, Step 1, starting from 2-phenoxyethanol (3.7 g, 26.8 mmol), 2,3-dichloroquinoxaline (1.33 g, 6.7 mmol) and KO-t-Bu (0.75 g, 6.7 mmol): yield 0.74 g (37%); mp 99.5-101.5° C., HRMS m/z calcd for C16H13CIN2O2(M)+300.0666, found 300.0672. Ana... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | c1ccc2nccnc2c1.c1ccccc1 | HCl | null | null | null | Clc1nc2ccccc2nc1Cl.OCCOc1ccccc1>>Clc1nc2ccccc2nc1OCCOc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c401697294ae4fec9e6ff7729b9cf9ee | Nc1nc2c(O)cccc2o1.O=C1OCCO1>>Nc1nc2c(OCCO)cccc2o1 | OC1=CC=CC2=C1N=C(O2)N.C1(OCCO1)=O>>OCCOC1=CC=CC2=C1N=C(O2)N | [NH2:1][c:2]1[n:3][c:4]2[c:5]([OH:6])[cH:10][cH:11][cH:12][c:13]2[o:14]1.O=C1O[CH2:7][CH2:8][O:9]1>>[NH2:1][c:2]1[n:3][c:4]2[c:5]([O:6][CH2:7][CH2:8][OH:9])[cH:10][cH:11][cH:12][c:13]2[o:14]1 | Nc1nc2c(O)cccc2o1.O=C1OCCO1 | Nc1nc2c(OCCO)cccc2o1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 34950df4dc1bc6c778d9cfa26c728e443e4886f7382a4283f1fbae4a959b8c37 | c6f5c5ba2d936b513bc18d6bcb095f40591aa3ba8700a9f5b8ecbbdd690dab72 | c1ccc2ocnc2c1 | O=C1-O-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1>>[OH;D1;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1 | 46 | [{"value": 46.0, "product": "OCCOC1=CC=CC2=C1N=C(O2)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared according to the procedure of Example 91, Step 1, starting from 4-hydroxy-2-amino-1,3-benzoxazol*(0.97 g, 6.5 mmol) and ethylene carbonate (0.63 g, 7.1 mmol). Solid; yield 46%; mp 124-126° C. Anal. (C9H10N2O3) C, H, N.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Aromatic alcohol | Ether.Primary alcohol | C1COCO1 | null | c1ccc2ocnc2c1 | Other | null | null | null | Nc1nc2c(O)cccc2o1.O=C1OCCO1>>Nc1nc2c(OCCO)cccc2o1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-79616e307bb14938ae98eb0606b016dc | Clc1nccnc1Cl.Nc1nc2c(OCCO)cccc2o1>>Nc1nc2c(OCCOc3nccnc3Cl)cccc2o1 | [H-].[Na+].ClC1=NC=CN=C1Cl.OCCOC1=CC=CC2=C1N=C(O2)N>>ClC=1C(=NC=CN1)OCCOC1=CC=CC2=C1N=C(O2)N | Cl[c:10]1[n:11][cH:12][cH:13][n:14][c:15]1[Cl:16].[NH2:1][c:2]1[n:3][c:4]2[c:5]([O:6][CH2:7][CH2:8][OH:9])[cH:17][cH:18][cH:19][c:20]2[o:21]1>>[NH2:1][c:2]1[n:3][c:4]2[c:5]([O:6][CH2:7][CH2:8][O:9][c:10]3[n:11][cH:12][cH:13][n:14][c:15]3[Cl:16])[cH:17][cH:18][cH:19][c:20]2[o:21]1 | Clc1nccnc1Cl.Nc1nc2c(OCCO)cccc2o1 | Nc1nc2c(OCCOc3nccnc3Cl)cccc2o1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8088ac3623a2ee47f375f73ca665bec9cf80b1384463e6e2f03125aecbcea517 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1cc(OCCOc2cnccn2)c2ncoc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7] | null | [] | null | null | null | null | The title compound was prepared according to the procedure of Example 4, Step 1, except that 4 equiv of both NaH and 2,3-dichloropyrazine were used, starting from the product of Step 1. The reaction temperature was 90° C. The crude product was used directly in the next step.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cnccn1 | c1cnccn1 | c1cnccn1.c1ccc2ocnc2c1 | HCl | null | null | null | Clc1nccnc1Cl.Nc1nc2c(OCCO)cccc2o1>>Nc1nc2c(OCCOc3nccnc3Cl)cccc2o1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-878084f32b84467d9e14f8ec423f47c2 | Clc1nccnc1OCCOc1ccccc1.NC1CCNC1>>NC1CCN(c2nccnc2OCCOc2ccccc2)C1 | ClC1=NC=CN=C1OCCOC1=CC=CC=C1.NC1CNCC1>>NC1CN(CC1)C=1C(=NC=CN1)OCCOC1=CC=CC=C1 | Cl[c:6]1[n:7][cH:8][cH:9][n:10][c:11]1[O:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1.[NH2:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:22]1>>[NH2:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][cH:9][n:10][c:11]2[O:12][CH2:13][CH2:14][O:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:22]1 | Clc1nccnc1OCCOc1ccccc1.NC1CCNC1 | NC1CCN(c2nccnc2OCCOc2ccccc2)C1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 3718a28a2b74478a2d103a3d9228963a3a4beec5fae01aa8827f50881f47258a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OCCOc2nccnc2N2CCCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[C:8]1-[C:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:12]1-[C:8]-[C:9]-[C:10]-[C:11]-1 | null | [] | null | null | null | null | The title compound was prepared according to the procedure described in Example 4, Step 2, starting from 2-chloro-3-(2-phenoxyethoxy)pyrazine (150 mg, 0.60 mmol; from Example 1, Step 1) and 3-aminopyrrolidine (270 mg, 3.13 mmol) with the exception that a final extraction step between EtOAc and 5% aqueous NaOH was carri... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cnccn1.C1CCNC1 | C1CC[NH]C1.c1cnccn1 | C1CC[NH]C1.c1cnccn1.c1ccccc1 | HCl | null | null | null | Clc1nccnc1OCCOc1ccccc1.NC1CCNC1>>NC1CCN(c2nccnc2OCCOc2ccccc2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c8eeb22752c94585b96bc2732bf955bf | Clc1ccccc1OCCOc1nccnc1Cl.NC1CCNC1>>NC1CCN(c2nccnc2OCCOc2ccccc2Cl)C1 | ClC1=NC=CN=C1OCCOC1=C(C=CC=C1)Cl.NC1CNCC1>>NC1CN(CC1)C=1C(=NC=CN1)OCCOC1=C(C=CC=C1)Cl | Cl[c:6]1[n:7][cH:8][cH:9][n:10][c:11]1[O:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][cH:19][cH:20][c:21]1[Cl:22].[NH2:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:23]1>>[NH2:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][cH:9][n:10][c:11]2[O:12][CH2:13][CH2:14][O:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[Cl:22])[CH2:23]1 | Clc1ccccc1OCCOc1nccnc1Cl.NC1CCNC1 | NC1CCN(c2nccnc2OCCOc2ccccc2Cl)C1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 3718a28a2b74478a2d103a3d9228963a3a4beec5fae01aa8827f50881f47258a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OCCOc2nccnc2N2CCCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[C:8]1-[C:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:12]1-[C:8]-[C:9]-[C:10]-[C:11]-1 | null | [] | null | null | null | null | The title compound was prepared according to the procedure described in Example 4, Step 2, starting from 2-chloro-3-[2-(2-chlorophenoxy)ethoxy]pyrazine*(150 mg, 0.53 mmol) and 3-aminopyrrolidine (252 mg, 2.92 mmol) with the exception that a final extraction step between EtOAc and 5% aqueous NaOH was carried out. This g... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cnccn1.C1CCNC1 | C1CC[NH]C1.c1cnccn1 | C1CC[NH]C1.c1cnccn1.c1ccccc1 | HCl | null | null | null | Clc1ccccc1OCCOc1nccnc1Cl.NC1CCNC1>>NC1CCN(c2nccnc2OCCOc2ccccc2Cl)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4df59d3a4b0b454fb47ea96377dd82b9 | Clc1ccc(OCCOc2nccnc2Cl)cc1.NC1CCNC1>>NC1CCN(c2nccnc2OCCOc2ccc(Cl)cc2)C1 | ClC1=NC=CN=C1OCCOC1=CC=C(C=C1)Cl.NC1CNCC1>>NC1CN(CC1)C=1C(=NC=CN1)OCCOC1=CC=C(C=C1)Cl | Cl[c:6]1[n:7][cH:8][cH:9][n:10][c:11]1[O:12][CH2:13][CH2:14][O:15][c:16]1[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]1.[NH2:1][CH:2]1[CH2:3][CH2:4][NH:5][CH2:23]1>>[NH2:1][CH:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][cH:9][n:10][c:11]2[O:12][CH2:13][CH2:14][O:15][c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[CH2:23... | Clc1ccc(OCCOc2nccnc2Cl)cc1.NC1CCNC1 | NC1CCN(c2nccnc2OCCOc2ccc(Cl)cc2)C1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 3718a28a2b74478a2d103a3d9228963a3a4beec5fae01aa8827f50881f47258a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OCCOc2nccnc2N2CCCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[C:8]1-[C:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:12]1-[C:8]-[C:9]-[C:10]-[C:11]-1 | null | [] | null | null | null | null | The title compound was prepared according to the procedure described in Example 4, Step 2, starting from 2-chloro-3-[2-(4-chlorophenoxy)ethoxy]pyrazine*(150 mg, 0.53 mmol) and 3-aminopyrrolidine (247 mg, 2.87 mmol) with the exception that a final extraction step between EtOAc and 5% aqueous NaOH was carried out. This g... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cnccn1.C1CCNC1 | C1CC[NH]C1.c1cnccn1 | C1CC[NH]C1.c1cnccn1.c1ccccc1 | HCl | null | null | null | Clc1ccc(OCCOc2nccnc2Cl)cc1.NC1CCNC1>>NC1CCN(c2nccnc2OCCOc2ccc(Cl)cc2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9057f530008443ccaf62eebd59f6579c | C1CNCCNC1.Clc1nccnc1OCCOc1ccccc1>>c1ccc(OCCOc2nccnc2N2CCCNCC2)cc1 | ClC1=NC=CN=C1OCCOC1=CC=CC=C1.N1CCNCCC1>>N1(CCNCCC1)C=1C(=NC=CN1)OCCOC1=CC=CC=C1 | [NH:15]1[CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21]1.Cl[c:14]1[c:9]([O:8][CH2:7][CH2:6][O:5][c:4]2[cH:3][cH:2][cH:1][cH:23][cH:22]2)[n:10][cH:11][cH:12][n:13]1>>[cH:1]1[cH:2][cH:3][c:4]([O:5][CH2:6][CH2:7][O:8][c:9]2[n:10][cH:11][cH:12][n:13][c:14]2[N:15]2[CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21]2)[cH:22][cH:... | C1CNCCNC1.Clc1nccnc1OCCOc1ccccc1 | c1ccc(OCCOc2nccnc2N2CCCNCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 50c76379a2a3410ec3054629834c5862609090f07cd49a1d59ac4aa48b759aeb | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OCCOc2nccnc2N2CCCNCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[#7:8]-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[#7:8]-[C:9]-[C:10]-[N;H0;D3;+0:11](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7])-[C:12]-[C:13] | null | [] | null | null | null | null | The title compound was prepared according to the procedure described in Example 4, Step 2, starting from 2-chloro-3-(2-phenoxyethoxy)pyrazine (150 mg, 0.60 mmol; from Example 1, Step 1) and homopiperazine (250 mg, 2.5 mmol) with the exception that a final extraction step between EtOAc and 5% aqueous NaOH was carried ou... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCNC1.c1cnccn1 | c1cnccn1.C1C[NH]CCNC1 | c1ccccc1.c1cnccn1.C1C[NH]CCNC1 | HCl | null | null | null | C1CNCCNC1.Clc1nccnc1OCCOc1ccccc1>>c1ccc(OCCOc2nccnc2N2CCCNCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f5d9959aa2d04904a8ccfb486b67a822 | C1CNCCNC1.Clc1nccnc1OCC1COc2ccccc2O1>>c1ccc2c(c1)OCC(COc1nccnc1N1CCCNCC1)O2 | ClC1=NC=CN=C1OCC1COC2=C(O1)C=CC=C2.N1CCNCCC1>>N1(CCNCCC1)C=1C(=NC=CN1)OCC1COC2=C(O1)C=CC=C2 | [NH:18]1[CH2:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24]1.Cl[c:17]1[c:12]([O:11][CH2:10][CH:9]2[CH2:8][O:7][c:5]3[c:4]([cH:3][cH:2][cH:1][cH:6]3)[O:25]2)[n:13][cH:14][cH:15][n:16]1>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[O:7][CH2:8][CH:9]([CH2:10][O:11][c:12]1[n:13][cH:14][cH:15][n:16][c:17]1[N:18]1[CH2:19][CH2:20][CH2... | C1CNCCNC1.Clc1nccnc1OCC1COc2ccccc2O1 | c1ccc2c(c1)OCC(COc1nccnc1N1CCCNCC1)O2 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 50c76379a2a3410ec3054629834c5862609090f07cd49a1d59ac4aa48b759aeb | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2c(c1)OCC(COc1nccnc1N1CCCNCC1)O2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[#7:8]-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[#7:8]-[C:9]-[C:10]-[N;H0;D3;+0:11](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7])-[C:12]-[C:13] | null | [] | null | null | null | null | The title compound was prepared according to the procedure described in Example 4, Step 2, starting from 2-chloro-3-(2,3-dihydro-1,4-benzodioxin-2-ylmethoxy)pyrazine* (150 mg, 0.54 mmol) and homopiperazine (266 mg, 2.66 mmol) with the exception that a final extraction step between EtOAc and 5% aqueous NaOH was carried ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCNC1.c1cnccn1 | c1cnccn1.C1C[NH]CCNC1 | c1ccc2c(c1)OCCO2.c1cnccn1.C1C[NH]CCNC1 | HCl | null | null | null | C1CNCCNC1.Clc1nccnc1OCC1COc2ccccc2O1>>c1ccc2c(c1)OCC(COc1nccnc1N1CCCNCC1)O2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c0f7b8e1a444474683b7d98b073af725 | C1CNCCNC1.Clc1ccc(OCCOc2nccnc2Cl)cc1>>Clc1ccc(OCCOc2nccnc2N2CCCNCC2)cc1 | ClC1=NC=CN=C1OCCOC1=CC=C(C=C1)Cl.N1CCNCCC1>>N1(CCNCCC1)C=1C(=NC=CN1)OCCOC1=CC=C(C=C1)Cl | [NH:16]1[CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1.Cl[c:15]1[c:10]([O:9][CH2:8][CH2:7][O:6][c:5]2[cH:4][cH:3][c:2]([Cl:1])[cH:24][cH:23]2)[n:11][cH:12][cH:13][n:14]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][O:9][c:10]2[n:11][cH:12][cH:13][n:14][c:15]2[N:16]2[CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22... | C1CNCCNC1.Clc1ccc(OCCOc2nccnc2Cl)cc1 | Clc1ccc(OCCOc2nccnc2N2CCCNCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 50c76379a2a3410ec3054629834c5862609090f07cd49a1d59ac4aa48b759aeb | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OCCOc2nccnc2N2CCCNCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[#7:8]-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[#7:8]-[C:9]-[C:10]-[N;H0;D3;+0:11](-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7])-[C:12]-[C:13] | null | [] | null | null | null | null | The title compound was prepared according to the procedure described in Example 4, Step 2, starting from 2-chloro-3-[2-(4-chlorophenoxy)ethoxy]pyrazine*(150 mg, 0.53 mmol) and homopiperazine (287 mg, 2.87 mmol) with the exception that a final extraction step between EtOAc and 5% aqueous NaOH was carried out. This gave ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCNC1.c1cnccn1 | c1cnccn1.C1C[NH]CCNC1 | c1ccccc1.c1cnccn1.C1C[NH]CCNC1 | HCl | null | null | null | C1CNCCNC1.Clc1ccc(OCCOc2nccnc2Cl)cc1>>Clc1ccc(OCCOc2nccnc2N2CCCNCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-98ddbc642b71400bbdef4d0d6f990e92 | CC1CNCCN1.Clc1nccnc1OCCOc1ccccc1>>CC1CN(c2nccnc2OCCOc2ccccc2)CCN1 | ClC1=NC=CN=C1OCCOC1=CC=CC=C1.CC1NCCNC1>>CC1CN(CCN1)C=1C(=NC=CN1)OCCOC1=CC=CC=C1 | [CH3:1][CH:2]1[CH2:3][NH:4][CH2:21][CH2:22][NH:23]1.Cl[c:5]1[n:6][cH:7][cH:8][n:9][c:10]1[O:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[CH3:1][CH:2]1[CH2:3][N:4]([c:5]2[n:6][cH:7][cH:8][n:9][c:10]2[O:11][CH2:12][CH2:13][O:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22][NH:23]1 | CC1CNCCN1.Clc1nccnc1OCCOc1ccccc1 | CC1CN(c2nccnc2OCCOc2ccccc2)CCN1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | aca68f5bce32bd07877d7a9740aa72beb2e113749fe78e75419bc629adec91e0 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OCCOc2nccnc2N2CCNCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | The title compound was prepared according to the procedure described in Example 4. Step 2, starting from 2-chloro-3-(2-phenoxyethoxy)pyrazine (150 mg, 0.54 mmol, from Example 1, Step 1) and 2-methylpiperazine (250 mg, 2.5 mmol) with the exception that a final extraction step between EtOAc and 5% aqueous NaOH was carrie... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cnccn1 | C1CNCC[NH]1.c1cnccn1 | C1CNCC[NH]1.c1cnccn1.c1ccccc1 | HCl | null | null | null | CC1CNCCN1.Clc1nccnc1OCCOc1ccccc1>>CC1CN(c2nccnc2OCCOc2ccccc2)CCN1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5b84485a5a9c4279a963eefc35bdd754 | CC1CNCCN1.Clc1ccc(OCCOc2nccnc2Cl)cc1>>CC1CN(c2nccnc2OCCOc2ccc(Cl)cc2)CCN1 | ClC1=NC=CN=C1OCCOC1=CC=C(C=C1)Cl.CC1NCCNC1>>CC1CN(CCN1)C=1C(=NC=CN1)OCCOC1=CC=C(C=C1)Cl | [CH3:1][CH:2]1[CH2:3][NH:4][CH2:22][CH2:23][NH:24]1.Cl[c:5]1[n:6][cH:7][cH:8][n:9][c:10]1[O:11][CH2:12][CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]1>>[CH3:1][CH:2]1[CH2:3][N:4]([c:5]2[n:6][cH:7][cH:8][n:9][c:10]2[O:11][CH2:12][CH2:13][O:14][c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][cH:21]2)[CH2:22]... | CC1CNCCN1.Clc1ccc(OCCOc2nccnc2Cl)cc1 | CC1CN(c2nccnc2OCCOc2ccc(Cl)cc2)CCN1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | aca68f5bce32bd07877d7a9740aa72beb2e113749fe78e75419bc629adec91e0 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OCCOc2nccnc2N2CCNCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | The title compound was prepared according to the procedure described in Example 4, Step 2, starting from 2-chloro-3-[2-(4-chlorophenoxy)ethoxy]pyrazine*(150 mg, 0.53 mmol) and 2-methylpiperazine (256 mg, 2.56 mmol) with the exception that a final extraction step between EtOAc and 5% aqueous NaOH was carried out. This g... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cnccn1 | C1CNCC[NH]1.c1cnccn1 | C1CNCC[NH]1.c1cnccn1.c1ccccc1 | HCl | null | null | null | CC1CNCCN1.Clc1ccc(OCCOc2nccnc2Cl)cc1>>CC1CN(c2nccnc2OCCOc2ccc(Cl)cc2)CCN1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f5791e102c0343dfa8efa4580994199c | CC1CNCCN1.COc1ccccc1OCC(C)Oc1nccnc1Cl>>COc1ccccc1OCC(C)Oc1nccnc1N1CCNC(C)C1 | ClC1=NC=CN=C1OC(COC1=C(C=CC=C1)OC)C.CC1NCCNC1>>CC1CN(CCN1)C=1C(=NC=CN1)OC(COC1=C(C=CC=C1)OC)C | [NH:20]1[CH2:21][CH2:22][NH:23][CH:24]([CH3:25])[CH2:26]1.Cl[c:19]1[c:14]([O:13][CH:11]([CH2:10][O:9][c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[CH3:12])[n:15][cH:16][cH:17][n:18]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][CH:11]([CH3:12])[O:13][c:14]1[n:15][cH:16][cH:17][n:18][c:19]1[N:20]... | CC1CNCCN1.COc1ccccc1OCC(C)Oc1nccnc1Cl | COc1ccccc1OCC(C)Oc1nccnc1N1CCNC(C)C1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 76b5a96b5c73afc00c162a6d1bfbc74a19ffca41d4e87b05da47a491d82e0c1f | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OCCOc2nccnc2N2CCNCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | The title compound was prepared according to the procedure described in Example 4, Step 2, starting from 2-chloro-3-[2-(2-methoxyphenoxy)-1-methylethoxy]pyrazine* (150 mg, 0.51 mmol) and 2-methylpiperazine (260 mg, 2.6 mmol) with the exception that a final extraction step between EtOAc and 5% aqueous NaOH was carried o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cnccn1 | c1cnccn1.C1C[NH]CCN1 | c1ccccc1.c1cnccn1.C1C[NH]CCN1 | HCl | null | null | null | CC1CNCCN1.COc1ccccc1OCC(C)Oc1nccnc1Cl>>COc1ccccc1OCC(C)Oc1nccnc1N1CCNC(C)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-16f323ae09594cbd9729c4735b9836cc | CC1CNCCN1.Clc1nccnc1OCC1COc2ccccc2O1>>CC1CN(c2nccnc2OCC2COc3ccccc3O2)CCN1 | ClC1=NC=CN=C1OCC1COC2=C(O1)C=CC=C2.CC1NCCNC1>>CC1CN(CCN1)C=1C(=NC=CN1)OCC1COC2=C(O1)C=CC=C2 | [CH3:1][CH:2]1[CH2:3][NH:4][CH2:23][CH2:24][NH:25]1.Cl[c:5]1[n:6][cH:7][cH:8][n:9][c:10]1[O:11][CH2:12][CH:13]1[CH2:14][O:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[O:22]1>>[CH3:1][CH:2]1[CH2:3][N:4]([c:5]2[n:6][cH:7][cH:8][n:9][c:10]2[O:11][CH2:12][CH:13]2[CH2:14][O:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[O:2... | CC1CNCCN1.Clc1nccnc1OCC1COc2ccccc2O1 | CC1CN(c2nccnc2OCC2COc3ccccc3O2)CCN1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | aca68f5bce32bd07877d7a9740aa72beb2e113749fe78e75419bc629adec91e0 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2c(c1)OCC(COc1nccnc1N1CCNCC1)O2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | The title compound was prepared according to the procedure described in Example 4, Step 2, starting from 2-chloro-3-(2,3-dihydro-1,4-benzodioxin-2-ylmethoxy)pyrazine* (150 mg, 0.54 mmol) and 2-methylpiperazine (293 mg, 2.92 mmol) with the exception that a final extraction step between EtOAc and 5% aqueous NaOH was carr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cnccn1 | C1CNCC[NH]1.c1cnccn1 | C1CNCC[NH]1.c1cnccn1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | CC1CNCCN1.Clc1nccnc1OCC1COc2ccccc2O1>>CC1CN(c2nccnc2OCC2COc3ccccc3O2)CCN1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dfdd6ad1a62c4d3eb193aab59e690321 | CCN1CCNCC1.Clc1nccnc1OCCOc1ccccc1>>CCN1CCN(c2nccnc2OCCOc2ccccc2)CC1 | ClC1=NC=CN=C1OCCOC1=CC=CC=C1.C(C)N1CCNCC1>>C(C)N1CCN(CC1)C=1C(=NC=CN1)OCCOC1=CC=CC=C1 | [CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][NH:6][CH2:23][CH2:24]1.Cl[c:7]1[n:8][cH:9][cH:10][n:11][c:12]1[O:13][CH2:14][CH2:15][O:16][c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[n:8][cH:9][cH:10][n:11][c:12]2[O:13][CH2:14][CH2:15][O:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[... | CCN1CCNCC1.Clc1nccnc1OCCOc1ccccc1 | CCN1CCN(c2nccnc2OCCOc2ccccc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 343e2e4205e268ef018e3d4960cb45b93370e1763fb33dc0e04e91f5357b5af3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OCCOc2nccnc2N2CCNCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | The title compound was prepared according to the procedure described in Example 4, Step 2, starting from 2-chloro-3-(2-phenoxyethoxy)pyrazine (150 mg, 0.60 mmol; from Example 1, Step 1) and N-ethylpiperazine (250 mg, 2.19 mmol) with the exception that a final extraction step between EtOAc and 5% aqueous NaOH was carrie... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1.c1ccccc1 | HCl | null | null | null | CCN1CCNCC1.Clc1nccnc1OCCOc1ccccc1>>CCN1CCN(c2nccnc2OCCOc2ccccc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-172fa0dfa37f4bf6b976ef9be5c37cec | CCN1CCNCC1.Clc1ccccc1OCCOc1nccnc1Cl>>CCN1CCN(c2nccnc2OCCOc2ccccc2Cl)CC1 | ClC1=NC=CN=C1OCCOC1=C(C=CC=C1)Cl.C(C)N1CCNCC1>>C(C)N1CCN(CC1)C=1C(=NC=CN1)OCCOC1=C(C=CC=C1)Cl | [CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][NH:6][CH2:24][CH2:25]1.Cl[c:7]1[n:8][cH:9][cH:10][n:11][c:12]1[O:13][CH2:14][CH2:15][O:16][c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[Cl:23]>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[n:8][cH:9][cH:10][n:11][c:12]2[O:13][CH2:14][CH2:15][O:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:2... | CCN1CCNCC1.Clc1ccccc1OCCOc1nccnc1Cl | CCN1CCN(c2nccnc2OCCOc2ccccc2Cl)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 343e2e4205e268ef018e3d4960cb45b93370e1763fb33dc0e04e91f5357b5af3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OCCOc2nccnc2N2CCNCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | The title compound was prepared in an analogous manner to Example 4, Step 2, starting from 2-chloro-3-[2-(2-chlorophenoxy)ethoxy]pyrazine*(150 mg, 0.53 mmol) and N-ethylpiperazine (221 mg, 1.93 mmol) with the exception that a final extraction step between EtOAc and 5% aqueous NaOH was carried out. This gave 100 mg (52%... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1.c1ccccc1 | HCl | null | null | null | CCN1CCNCC1.Clc1ccccc1OCCOc1nccnc1Cl>>CCN1CCN(c2nccnc2OCCOc2ccccc2Cl)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c4563ffa2f824361962f06d8f903b590 | CCN1CCNCC1.Clc1ccc(OCCOc2nccnc2Cl)cc1>>CCN1CCN(c2nccnc2OCCOc2ccc(Cl)cc2)CC1 | ClC1=NC=CN=C1OCCOC1=CC=C(C=C1)Cl.C(C)N1CCNCC1>>C(C)N1CCN(CC1)C=1C(=NC=CN1)OCCOC1=CC=C(C=C1)Cl | [CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][NH:6][CH2:24][CH2:25]1.Cl[c:7]1[n:8][cH:9][cH:10][n:11][c:12]1[O:13][CH2:14][CH2:15][O:16][c:17]1[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[n:8][cH:9][cH:10][n:11][c:12]2[O:13][CH2:14][CH2:15][O:16][c:17]2[cH:18][cH:19][c:20]([Cl:21])[... | CCN1CCNCC1.Clc1ccc(OCCOc2nccnc2Cl)cc1 | CCN1CCN(c2nccnc2OCCOc2ccc(Cl)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 343e2e4205e268ef018e3d4960cb45b93370e1763fb33dc0e04e91f5357b5af3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OCCOc2nccnc2N2CCNCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | The title compound was prepared according to the procedure described in Example 4. Step 2, starting from 2-chloro-3-[2-(4-chlorophenoxy)ethoxy]pyrazine*(150 mg, 0.53 mmol) and N-ethylpiperazine (221 mg, 1.93 mmol) with the exception that a final extraction step between EtOAc and 5% aqueous NaOH was carried out. This ga... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1.c1ccccc1 | HCl | null | null | null | CCN1CCNCC1.Clc1ccc(OCCOc2nccnc2Cl)cc1>>CCN1CCN(c2nccnc2OCCOc2ccc(Cl)cc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-42499fdd3c6846ccb99c1096b54c7f10 | CCN1CCNCC1.Clc1nccnc1OCC1COc2ccccc2O1>>CCN1CCN(c2nccnc2OCC2COc3ccccc3O2)CC1 | ClC1=NC=CN=C1OCC1COC2=C(O1)C=CC=C2.C(C)N1CCNCC1>>C(C)N1CCN(CC1)C=1C(=NC=CN1)OCC1COC2=C(O1)C=CC=C2 | [CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][NH:6][CH2:25][CH2:26]1.Cl[c:7]1[n:8][cH:9][cH:10][n:11][c:12]1[O:13][CH2:14][CH:15]1[CH2:16][O:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[O:24]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[n:8][cH:9][cH:10][n:11][c:12]2[O:13][CH2:14][CH:15]2[CH2:16][O:17][c:18]3[cH:19][cH:20][c... | CCN1CCNCC1.Clc1nccnc1OCC1COc2ccccc2O1 | CCN1CCN(c2nccnc2OCC2COc3ccccc3O2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 343e2e4205e268ef018e3d4960cb45b93370e1763fb33dc0e04e91f5357b5af3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2c(c1)OCC(COc1nccnc1N1CCNCC1)O2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | The title compound was prepared according to the procedure described in Example 4, Step 2, starting from 2-chloro-3-(2,3-dihydro-1,4-benzodioxin-2-ylmethoxy)pyrazine* (150 mg, 0.54 mmol) and N-ethylpiperazine (219 mg, 1.92 mmol) with the exception that a final extraction step between EtOAc and 5% aqueous NaOH was carri... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1.c1ccc2c(c1)OCCO2 | HCl | null | null | null | CCN1CCNCC1.Clc1nccnc1OCC1COc2ccccc2O1>>CCN1CCN(c2nccnc2OCC2COc3ccccc3O2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a393246af1304ea3bfe64e2e2b8408b1 | CCN1CCNCC1.COc1ccccc1OCC(C)Oc1nccnc1Cl>>CCN1CCN(c2nccnc2OC(C)COc2ccccc2OC)CC1 | ClC1=NC=CN=C1OC(COC1=C(C=CC=C1)OC)C.C(C)N1CCNCC1>>C(C)N1CCN(CC1)C=1C(=NC=CN1)OC(COC1=C(C=CC=C1)OC)C | [CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][NH:6][CH2:26][CH2:27]1.Cl[c:7]1[n:8][cH:9][cH:10][n:11][c:12]1[O:13][CH:14]([CH3:15])[CH2:16][O:17][c:18]1[cH:19][cH:20][cH:21][cH:22][c:23]1[O:24][CH3:25]>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[n:8][cH:9][cH:10][n:11][c:12]2[O:13][CH:14]([CH3:15])[CH2:16][O:17][c:18]2[cH:19]... | CCN1CCNCC1.COc1ccccc1OCC(C)Oc1nccnc1Cl | CCN1CCN(c2nccnc2OC(C)COc2ccccc2OC)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 343e2e4205e268ef018e3d4960cb45b93370e1763fb33dc0e04e91f5357b5af3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OCCOc2nccnc2N2CCNCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | The title compound was prepared according to the procedure described in Example 4, Step 2, starting from 2-chloro-3-[2-(2-methoxyphenoxy)-1-methylethoxy]pyrazine* (150 mg, 0.51 mmol) and N-ethylpiperazine (222 mg, 1.94 mmol) with the exception that a final extraction step between EtOAc and 5% aqueous NaOH was carried o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1.c1ccccc1 | HCl | null | null | null | CCN1CCNCC1.COc1ccccc1OCC(C)Oc1nccnc1Cl>>CCN1CCN(c2nccnc2OC(C)COc2ccccc2OC)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dbe8f8dd9eac420d90e79e467c6f4854 | C1CO1.Clc1nccnc1Cl.Oc1cccc(Br)c1>>Clc1nccnc1OCCOc1cccc(Br)c1 | ClC1=NC=CN=C1Cl.BrC=1C=C(C=CC1)O.C1CO1.O([K])C(C)(C)C>>ClC=1C(=NC=CN1)OCCOC1=CC(=CC=C1)Br | [O:8]1[CH2:9][CH2:10]1.Cl[c:7]1[c:2]([Cl:1])[n:3][cH:4][cH:5][n:6]1.[OH:11][c:12]1[cH:13][cH:14][cH:15][c:16]([Br:17])[cH:18]1>>[Cl:1][c:2]1[n:3][cH:4][cH:5][n:6][c:7]1[O:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][c:16]([Br:17])[cH:18]1 | C1CO1.Clc1nccnc1Cl.Oc1cccc(Br)c1 | Clc1nccnc1OCCOc1cccc(Br)c1 | null | CCN(CC)CC | O1CCOCC1.C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 4813dcc234d7942566fb1884cd5adb05180bbc42d7501c3f9e0eda1e206010a3 | b000f52b510e329bf6a3592317078c1878a4c82ed29bc7f47d9ff9db738343ca | c1ccc(OCCOc2cnccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[C:8]1-[CH2;D2;+0:9]-[O;H0;D2;+0:10]-1.[OH;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[Cl;D1;H0:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:10]-[C:8]-[CH2;D2;+0:9]-[O;H0;D2;+0:11]-[c:12](:[c:13]):[c:14] | 75 | [{"value": 75.0, "product": "ClC=1C(=NC=CN1)OCCOC1=CC(=CC=C1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.5, "product": "ClC=1C(=NC=CN1)OCCOC1=CC(=CC=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | A mixture of 3-bromophenol (1.73 g, 10.0 mmol), ethylene oxide (0.44 g, 10 mmol). Et3N (3 drops) and dioxane (4 mL) was heated at 100° C. in a sealed tube for 2 d. The solution was cooled in an ice-bath and KO-t-Bu (1.07 g, 9.50 mmol) followed by 2,3-dichloropyrazine (1.34 g, 9 mmol) were added along with dioxane (1 mL... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Aromatic alcohol | Ether.Ether | C1CO1.c1cnccn1 | c1cnccn1 | c1cnccn1.c1ccccc1 | HCl | CCN(CC)CC.O1CCOCC1.C(Cl)Cl | null | 1.5 | C1CO1.Clc1nccnc1Cl.Oc1cccc(Br)c1>CCN(CC)CC.O1CCOCC1.C(Cl)Cl>Clc1nccnc1OCCOc1cccc(Br)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3aaf611856bb4041a612001264e3dbc8 | C1CNCCN1.Clc1nccnc1OCCOc1cccc(Br)c1>>Brc1cccc(OCCOc2nccnc2N2CCNCC2)c1 | N1CCNCC1.C(=O)([O-])[O-].[K+].[K+].ClC=1C(=NC=CN1)OCCOC1=CC(=CC=C1)Br>>N1(CCNCC1)C=1C(=NC=CN1)OCCOC1=CC(=CC=C1)Br | [NH:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1.Cl[c:16]1[c:11]([O:10][CH2:9][CH2:8][O:7][c:6]2[cH:5][cH:4][cH:3][c:2]([Br:1])[cH:23]2)[n:12][cH:13][cH:14][n:15]1>>[Br:1][c:2]1[cH:3][cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][O:10][c:11]2[n:12][cH:13][cH:14][n:15][c:16]2[N:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)[cH:23... | C1CNCCN1.Clc1nccnc1OCCOc1cccc(Br)c1 | Brc1cccc(OCCOc2nccnc2N2CCNCC2)c1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 76b5a96b5c73afc00c162a6d1bfbc74a19ffca41d4e87b05da47a491d82e0c1f | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OCCOc2nccnc2N2CCNCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | 85 | [{"value": 85.0, "product": "N1(CCNCC1)C=1C(=NC=CN1)OCCOC1=CC(=CC=C1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.9, "product": "N1(CCNCC1)C=1C(=NC=CN1)OCCOC1=CC(=CC=C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Piperazine (1.29 g, 15.0 mmol) and K2CO3 (0.69 g, 5.0 mmol) were added to a solution of 2-(3-bromophenoxy)ethyl 3-chloro-2-pyrazinyl ether (1.65 g, 5.00 mmol) in acetonitrile (25 mL) at room temperature. The mixture was heated at reflux for 21 h, allowed to cool, concentrated and the residue was partitioned between wat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cnccn1 | c1cnccn1.C1C[NH]CCN1 | c1ccccc1.c1cnccn1.C1C[NH]CCN1 | HCl | C(C)#N | null | null | C1CNCCN1.Clc1nccnc1OCCOc1cccc(Br)c1>C(C)#N>Brc1cccc(OCCOc2nccnc2N2CCNCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c016317b7e1e4fc298371001560eed63 | Clc1nc2ccccc2nc1Cl.OCCOc1ccccc1Cl>>Clc1ccccc1OCCOc1nc2ccccc2nc1Cl | ClC1=NC2=CC=CC=C2N=C1Cl.ClC1=C(OCCO)C=CC=C1.[H-].[Na+]>>ClC1=NC2=CC=CC=C2N=C1OCCOC1=C(C=CC=C1)Cl | Cl[c:12]1[n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[n:20][c:21]1[Cl:22].[Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[O:8][CH2:9][CH2:10][OH:11]>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[O:8][CH2:9][CH2:10][O:11][c:12]1[n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[n:20][c:21]1[Cl:22] | Clc1nc2ccccc2nc1Cl.OCCOc1ccccc1Cl | Clc1ccccc1OCCOc1nc2ccccc2nc1Cl | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 76f684f6591b23c199df9d989c265ce73ff618d868cc26b6ec9cabfd7980b054 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(OCCOc2cnc3ccccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7] | null | [] | null | null | 3 | HOUR | 2-(2-Chlorophenoxy)ethanol (0.229 g, 1.33 mmol) was treated with NaH (55% dispersion in mineral oil; 0.058 g, 1.33 mmol) in dioxane (2 mL). After stirring at room temperature for 3 h, the mixture was added dropwise to a slurry of 2,3-dichloroquinoxaline (0.320 g, 1.60 mmol) in dioxane (1 mL). The resulting mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | c1ccccc1.c1ccc2nccnc2c1 | HCl | O1CCOCC1 | null | 3 | Clc1nc2ccccc2nc1Cl.OCCOc1ccccc1Cl>O1CCOCC1>Clc1ccccc1OCCOc1nc2ccccc2nc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-782c4e42a4d04b6787f69603abe08fa3 | C1CNCCN1.Clc1ccccc1OCCOc1nc2ccccc2nc1Cl>>Clc1ccccc1OCCOc1nc2ccccc2nc1N1CCNCC1 | N1CCNCC1.ClC1=NC2=CC=CC=C2N=C1OCCOC1=C(C=CC=C1)Cl>>ClC1=C(OCCOC2=NC3=CC=CC=C3N=C2N2CCNCC2)C=CC=C1 | [NH:22]1[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]1.Cl[c:21]1[c:12]([O:11][CH2:10][CH2:9][O:8][c:7]2[c:2]([Cl:1])[cH:3][cH:4][cH:5][cH:6]2)[n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[n:20]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[O:8][CH2:9][CH2:10][O:11][c:12]1[n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[n:2... | C1CNCCN1.Clc1ccccc1OCCOc1nc2ccccc2nc1Cl | Clc1ccccc1OCCOc1nc2ccccc2nc1N1CCNCC1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 678d34c35338404be7cc405e43966a4086710a7eff0ca432e8cc0a9367151dda | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OCCOc2nc3ccccc3nc2N2CCNCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[#8:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | 22 | [{"value": 22.0, "product": "ClC1=C(OCCOC2=NC3=CC=CC=C3N=C2N2CCNCC2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | Piperazine (0.580 g, 6.65 mmol) was added to the crude material from Step 1 and the resulting mixture was stirred at room temperature for 5 h. The solvent was evaporated, and the crude mixture was dissolved in DMSO and precipitated with water. The precipitate was purified by chromatography on silica gel using EtOAc/HOA... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccc2nccnc2c1 | c1ccc2nccnc2c1.C1C[NH]CCN1 | c1ccccc1.c1ccc2nccnc2c1.C1C[NH]CCN1 | HCl | null | null | 5 | C1CNCCN1.Clc1ccccc1OCCOc1nc2ccccc2nc1Cl>>Clc1ccccc1OCCOc1nc2ccccc2nc1N1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-64a6e142ee7045c5aa212794861cdc03 | Clc1nccnc1Cl.NCCOc1ccccc1>>Clc1nccnc1NCCOc1ccccc1 | O(C1=CC=CC=C1)CCN.ClC1=NC=CN=C1Cl.C(=O)([O-])[O-].[K+].[K+]>>ClC1=NC=CN=C1NCCOC1=CC=CC=C1 | Cl[c:7]1[c:2]([Cl:1])[n:3][cH:4][cH:5][n:6]1.[NH2:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[Cl:1][c:2]1[n:3][cH:4][cH:5][n:6][c:7]1[NH:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | Clc1nccnc1Cl.NCCOc1ccccc1 | Clc1nccnc1NCCOc1ccccc1 | null | null | C(C)#N.CCOCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | d8d76a4347a32a5acf79894f48887cf8d745ba4ca5f91e54084ebdbe25f43c75 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(OCCNc2cnccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c: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]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7] | 49 | [{"value": 49.0, "product": "ClC1=NC=CN=C1NCCOC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.0, "product": "ClC1=NC=CN=C1NCCOC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | A mixture of 2-phenoxyethylamine (2.65 g, 19.3 mmol), 2,3-dichloropyrazine (2.88 g, 19.3 mmol) and K2CO3 (2.67 g, 19.3 mmol) in acetonitrile (8 mL) was stirred in a sealed tube for 12 h at room temperature, and for a further 9.5 h at 80° C. The reaction mixture was diluted with ether, filtered, and concentrated. The re... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cnccn1 | c1cnccn1 | c1cnccn1.c1ccccc1 | HCl | C(C)#N.CCOCC | null | 12 | Clc1nccnc1Cl.NCCOc1ccccc1>C(C)#N.CCOCC>Clc1nccnc1NCCOc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-544aee79e6574ff78bdf2db00c6fb96d | CNCCOc1ccccc1.Clc1nccnc1Cl>>CN(CCOc1ccccc1)c1nccnc1Cl | ClC1=NC=CN=C1Cl.CNCCOC1=CC=CC=C1>>ClC=1C(=NC=CN1)N(CCOC1=CC=CC=C1)C | [CH3:1][NH:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.Cl[c:12]1[n:13][cH:14][cH:15][n:16][c:17]1[Cl:18]>>[CH3:1][N:2]([CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[n:13][cH:14][cH:15][n:16][c:17]1[Cl:18] | CNCCOc1ccccc1.Clc1nccnc1Cl | CN(CCOc1ccccc1)c1nccnc1Cl | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | ee5c44ccb1cf678ef9fa44823f1ba607bfe62f7666f405c2b1451bbae3d826b3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(OCCNc2cnccn2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C;D1;H3:11]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[C;D1;H3:11])-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7] | 71 | [{"value": 71.0, "product": "ClC=1C(=NC=CN1)N(CCOC1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2,3-dichloropyrazine (6.64 g, 44.6 mmol) and N-methyl-N-(2-phenoxyethyl)amine* (4.5 g, 29.8 mmol) in DMF (5 mL) was placed in a sealed Pyrex tube and heated in a microwave oven (Labwell MW10) for 1×2 min followed by 2×1 min at 75 W. The mixture was concentrated and the resulting oil was purified by column ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cnccn1 | c1cnccn1 | c1ccccc1.c1cnccn1 | HCl | CN(C)C=O | null | null | CNCCOc1ccccc1.Clc1nccnc1Cl>CN(C)C=O>CN(CCOc1ccccc1)c1nccnc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8ff57be5427f4569bde3cf527b709aa1 | Clc1nccnc1OCCOc1ccccc1.OC1CCNC1>>c1ccc(OCCOc2nccnc2OC2CCNC2)cc1 | CCOC(=O)C.ClC1=NC=CN=C1OCCOC1=CC=CC=C1.N1CC(CC1)O.[H-].[Na+]>>N1CC(CC1)OC=1C(=NC=CN1)OCCOC1=CC=CC=C1 | Cl[c:14]1[c:9]([O:8][CH2:7][CH2:6][O:5][c:4]2[cH:3][cH:2][cH:1][cH:22][cH:21]2)[n:10][cH:11][cH:12][n:13]1.[OH:15][CH:16]1[CH2:17][CH2:18][NH:19][CH2:20]1>>[cH:1]1[cH:2][cH:3][c:4]([O:5][CH2:6][CH2:7][O:8][c:9]2[n:10][cH:11][cH:12][n:13][c:14]2[O:15][CH:16]2[CH2:17][CH2:18][NH:19][CH2:20]2)[cH:21][cH:22]1 | Clc1nccnc1OCCOc1ccccc1.OC1CCNC1 | c1ccc(OCCOc2nccnc2OC2CCNC2)cc1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | ecc4e9e0121e46a5b6f9138a411a607fd0129d7c39a025ab57e215a7842ff3a3 | 1f70dbbaebc288b3a5d3f37803812d9d22b151831cd4b8351080508554b19875 | c1ccc(OCCOc2nccnc2OC2CCNC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7].[#7:8]-[C:9]-[C:10](-[OH;D1;+0:11])-[C:12]>>[#7:8]-[C:9]-[C:10](-[O;H0;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#8:7])-[C:12] | 22 | [{"value": 22.0, "product": "N1CC(CC1)OC=1C(=NC=CN1)OCCOC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.0, "product": "N1CC(CC1)OC=1C(=NC=CN1)OCCOC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 2-Chloro-3-(2-phenoxyethoxy)pyrazine (150 mg, 0.60 mmol; from Example 1, Step 1) was added to a stirred mixture of 3-pyrrolidinol (260 mg, 2.99 mmol) and NaH (55% dispersion in mineral oil; 110 mg, 2.50 mmol) in dioxane (2 mL), and the reaction was stirred at room temperature for 2 h. EtOAc was added and the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary alcohol | Ether | c1cnccn1 | c1cnccn1 | c1ccccc1.c1cnccn1.C1CCNC1 | HCl | O1CCOCC1 | null | 2 | Clc1nccnc1OCCOc1ccccc1.OC1CCNC1>O1CCOCC1>c1ccc(OCCOc2nccnc2OC2CCNC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-58e76195f9b0407fb1650a8765693ea1 | CC(C)(C)OC(=O)N1CCC(O)CC1.Clc1nccnc1OCCOc1ccccc1>>c1ccc(OCCOc2nccnc2OC2CCNCC2)cc1 | ClC1=NC=CN=C1OCCOC1=CC=CC=C1.C(=O)(OC(C)(C)C)N1CCC(CC1)O>>N1CCC(CC1)OC=1C(=NC=CN1)OCCOC1=CC=CC=C1 | CC(C)(C)OC(=O)[N:19]1[CH2:18][CH2:17][CH:16]([OH:15])[CH2:21][CH2:20]1.Cl[c:14]1[c:9]([O:8][CH2:7][CH2:6][O:5][c:4]2[cH:3][cH:2][cH:1][cH:23][cH:22]2)[n:10][cH:11][cH:12][n:13]1>>[cH:1]1[cH:2][cH:3][c:4]([O:5][CH2:6][CH2:7][O:8][c:9]2[n:10][cH:11][cH:12][n:13][c:14]2[O:15][CH:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]... | CC(C)(C)OC(=O)N1CCC(O)CC1.Clc1nccnc1OCCOc1ccccc1 | c1ccc(OCCOc2nccnc2OC2CCNCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 607d03f0c5fadd9dc05beaac47b81736cddcb009902eaf13d085b8ca9fdbeece | 703e64b49f7cda3193db3c163bedc8d4f0b15e295c87685fc48bb8db280a0e6c | c1ccc(OCCOc2nccnc2OC2CCNCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4](-[OH;D1;+0:5])-[C:6]-[C:7]-1.Cl-[c;H0;D3;+0:8]1:[#7;a:9]:[c:10]:[c:11]:[#7;a:12]:[c:13]:1-[#8:14]>>[#8:14]-[c:13]1:[#7;a:12]:[c:11]:[c:10]:[#7;a:9]:[c;H0;D3;+0:8]:1-[O;H0;D2;+0:5]-[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:7]-[C:6]-1 | 35.5 | [{"value": 35.0, "product": "N1CCC(CC1)OC=1C(=NC=CN1)OCCOC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.5, "product": "N1CCC(CC1)OC=1C(=NC=CN1)OCCOC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared according to the procedure described in Example 49 starting from 2-chloro-3-(2-phenoxyethoxy)pyrazine (250 mg, 1.00 mmol; from Example 1, Step 1) and N-Boc-4-hydroxypiperidine (234 mg, 1.16 mmol) to give 112 mg (35%) of the title product. HRMS m/z calcd for C17H23N3O3(M)* 315.1583, found... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Secondary alcohol.Boc | Ether.Secondary amine | C1CC[NH]CC1.c1cnccn1 | c1cnccn1.C1CCNCC1 | c1ccccc1.c1cnccn1.C1CCNCC1 | HCl | null | null | null | CC(C)(C)OC(=O)N1CCC(O)CC1.Clc1nccnc1OCCOc1ccccc1>>c1ccc(OCCOc2nccnc2OC2CCNCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0ad0051db2c74da4bf97b6fb09b1e0f3 | CC(C)(C)OC(=O)N1CCNCC1.Clc1nccnc1Cl>>CC(C)(C)OC(=O)N1CCN(c2nccnc2Cl)CC1 | C(=O)(OC(C)(C)C)N1CCNCC1.C(=O)([O-])[O-].[K+].[K+].ClC1=NC=CN=C1Cl>>ClC1=NC=CN=C1N1CCN(CC1)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:19][CH2:20]1.Cl[c:12]1[n:13][cH:14][cH:15][n:16][c:17]1[Cl:18]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[n:13][cH:14][cH:15][n:16][c:17]2[Cl:18])[CH2:19][CH2:20]1 | CC(C)(C)OC(=O)N1CCNCC1.Clc1nccnc1Cl | CC(C)(C)OC(=O)N1CCN(c2nccnc2Cl)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 343e2e4205e268ef018e3d4960cb45b93370e1763fb33dc0e04e91f5357b5af3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cnc(N2CCNCC2)cn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[Cl;D1;H0:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[#7:8]-[C:9]-[C:10]-1 | 100 | [{"value": 100.0, "product": "ClC1=NC=CN=C1N1CCN(CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.6, "product": "ClC1=NC=CN=C1N1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 40 | HOUR | A mixture of N-Boc-piperazine (11.47 g, 61.5 mmol), K2CO3 (8.5 g, 61 mmol) and 2,3-dichloropyrazine (9.20 g, 61.7 mmol) in acetonitrile (100 mL) was stirred at 100° C. for 40 h. The reaction mixture was concentrated, dissolved in toluene, washed with water, dried (MgSO4), and concentrated. The residue was purified by c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1 | HCl | C(C)#N | 100 | 40 | CC(C)(C)OC(=O)N1CCNCC1.Clc1nccnc1Cl>C(C)#N>CC(C)(C)OC(=O)N1CCN(c2nccnc2Cl)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1011b1db4f9d47a8b328cacdff1850cb | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.COc1cccc(F)c1O>>COc1cccc(F)c1OCCOc1nccnc1N1CCNCC1 | FC1=C(C(=CC=C1)OC)O.C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(=NC=CN1)OCCO>>N1(CCNCC1)C=1C(=NC=CN1)OCCOC1=C(C=CC=C1OC)F | CC(C)(C)OC(=O)[N:23]1[CH2:22][CH2:21][N:20]([c:19]2[c:14]([O:13][CH2:12][CH2:11]O)[n:15][cH:16][cH:17][n:18]2)[CH2:25][CH2:24]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([F:8])[c:9]1[OH:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([F:8])[c:9]1[O:10][CH2:11][CH2:12][O:13][c:14]1[n:15][cH:16][cH:17][n:18][c:19]1[N:20]1... | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.COc1cccc(F)c1O | COc1cccc(F)c1OCCOc1nccnc1N1CCNCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c5ac0a953bd50ad6bbff24e5244495f1a91e36c5f9c02a4b443b397f6d418f9b | b0f0b3b5378653ea91e6fef29b9a760b125d67e9695c46e32b9093a79f821980 | c1ccc(OCCOc2nccnc2N2CCNCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.O-[CH2;D2;+0:7]-[C:8]-[#8:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[#8:9]-[C:8]-[CH2;D2;+0:7]-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13] | 66 | [{"value": 66.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared starting from 2-fluoro-6-methoxyphenol (178 mg, 1.25 mmol) and 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol (1.17 mmol; prepared in Example 52, Step 2) to give 230 mg (66%) of a yellow oil. HRMS m/z calcd for C17H21FN4O3(M)+348.1598, found 348.1602.
Conditions: See r... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Primary alcohol.Aromatic alcohol.Boc | Ether.Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.c1cnccn1.C1C[NH]CCN1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.COc1cccc(F)c1O>>COc1cccc(F)c1OCCOc1nccnc1N1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-24bd306b25124acdb30aaa45479a311b | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.COc1cc(C)ccc1O>>COc1cc(C)ccc1OCCOc1nccnc1N1CCNCC1 | COC1=C(C=CC(=C1)C)O.C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(=NC=CN1)OCCO>>N1(CCNCC1)C=1C(=NC=CN1)OCCOC1=C(C=C(C=C1)C)OC | CC(C)(C)OC(=O)[N:23]1[CH2:22][CH2:21][N:20]([c:19]2[c:14]([O:13][CH2:12][CH2:11]O)[n:15][cH:16][cH:17][n:18]2)[CH2:25][CH2:24]1.[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][cH:8][c:9]1[OH:10]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH3:6])[cH:7][cH:8][c:9]1[O:10][CH2:11][CH2:12][O:13][c:14]1[n:15][cH:16][cH:17][n:18][c:19]1[N:... | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.COc1cc(C)ccc1O | COc1cc(C)ccc1OCCOc1nccnc1N1CCNCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c5ac0a953bd50ad6bbff24e5244495f1a91e36c5f9c02a4b443b397f6d418f9b | b0f0b3b5378653ea91e6fef29b9a760b125d67e9695c46e32b9093a79f821980 | c1ccc(OCCOc2nccnc2N2CCNCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.O-[CH2;D2;+0:7]-[C:8]-[#8:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[#8:9]-[C:8]-[CH2;D2;+0:7]-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13] | 67 | [{"value": 67.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared starting from 2-methoxy-4-methylphenol (162 mg, 1.25 mmol) and 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol (1.00 mmol; prepared in Example 52, Step 2) to give 233 mg (67%) of a yellow solid. HRMS m/z calcd for C18H24N4O3(M)+344.1848, found 344.1839.
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Primary alcohol.Aromatic alcohol.Boc | Ether.Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.c1cnccn1.C1C[NH]CCN1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.COc1cc(C)ccc1O>>COc1cc(C)ccc1OCCOc1nccnc1N1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3aae3c42d05e410d82db956db9160f4e | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.COc1ccc(O)c(Cl)c1>>COc1ccc(OCCOc2nccnc2N2CCNCC2)c(Cl)c1 | ClC1=C(C=CC(=C1)OC)O.C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(=NC=CN1)OCCO.N(=NC(=O)OCC)C(=O)OCC>>N1(CCNCC1)C=1C(=NC=CN1)OCCOC1=C(C=C(C=C1)OC)Cl | CC(C)(C)OC(=O)[N:20]1[CH2:19][CH2:18][N:17]([c:16]2[c:11]([O:10][CH2:9][CH2:8]O)[n:12][cH:13][cH:14][n:15]2)[CH2:22][CH2:21]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([OH:7])[c:23]([Cl:24])[cH:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][O:10][c:11]2[n:12][cH:13][cH:14][n:15][c:16]2[N:17]2[CH2:18][CH2:19][N... | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.COc1ccc(O)c(Cl)c1 | COc1ccc(OCCOc2nccnc2N2CCNCC2)c(Cl)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c5ac0a953bd50ad6bbff24e5244495f1a91e36c5f9c02a4b443b397f6d418f9b | b0f0b3b5378653ea91e6fef29b9a760b125d67e9695c46e32b9093a79f821980 | c1ccc(OCCOc2nccnc2N2CCNCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.O-[CH2;D2;+0:7]-[C:8]-[#8:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[#8:9]-[C:8]-[CH2;D2;+0:7]-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13] | null | [] | null | null | null | null | The title compound was prepared starting from 2-chloro-4-methoxyphenol (103 mg, 0.65 mmol) and 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol (0.61 mmol; prepared in Example 52, Step 2) according to the procedure described in Example 52, Step 3, but utilizing diethyl azodicarboxylate (DEAD) instead o... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Primary alcohol.Aromatic alcohol.Boc | Ether.Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.c1cnccn1.C1C[NH]CCN1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.COc1ccc(O)c(Cl)c1>>COc1ccc(OCCOc2nccnc2N2CCNCC2)c(Cl)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-45c3ff1bfa84413d9285baf79542ac92 | CS(=O)(=O)c1cccc(N)c1>>CS(=O)(=O)c1cccc(O)c1 | Cl.CS(=O)(=O)C1=CC(=CC=C1)N.[OH-].[Na+].N(=O)[O-].[Na+].C(Cl)Cl>>CS(=O)(=O)C=1C=C(C=CC1)O | N[c:9]1[cH:8][cH:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[cH:11]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([OH:10])[cH:11]1 | CS(=O)(=O)c1cccc(N)c1 | CS(=O)(=O)c1cccc(O)c1 | null | null | O.O.C(Cl)Cl | Functional Group Interconversion | OtherReaction | 5476e3e4f8e8862ba087972a35863ca0b6ebf27577a68b3ac2018e9a7004c864 | ed7617b9cd113fcbf3232da782e35483fef55189a64648ab4bdbc41767cd9a80 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]>>[O;D1;H1:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 45.3 | [{"value": 40.0, "product": "CS(=O)(=O)C=1C=C(C=CC1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.3, "product": "CS(=O)(=O)C=1C=C(C=CC1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | The title compound was prepared by a slightly modified literature procedure.*3-aminophenyl methyl sulfone hydrochloride (1.18 g, 5.70 mmol) was suspended in water/CH2Cl2. The mixture was neutralized with 25% aqueous NaOH. The CH2Cl2 layer was isolated and evaporated to dryness. Aqueous H2SO4 (60%; 10 mL) was added to t... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | O.O.C(Cl)Cl | 0 | 0.5 | CS(=O)(=O)c1cccc(N)c1>O.O.C(Cl)Cl>CS(=O)(=O)c1cccc(O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-581178f75ec24e11934aa09faf8008df | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.Oc1cccc(N2CCOCC2)c1>>c1cc(OCCOc2nccnc2N2CCNCC2)cc(N2CCOCC2)c1 | N(=NC(=O)N(C)C)C(=O)N(C)C.C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(=NC=CN1)OCCO.N1(CCOCC1)C=1C=C(C=CC1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>N1(CCNCC1)C=1C(=NC=CN1)OCCOC1=CC(=CC=C1)N1CCOCC1 | CC(C)(C)OC(=O)[N:17]1[CH2:16][CH2:15][N:14]([c:13]2[c:8]([O:7][CH2:6][CH2:5][OH:4])[n:9][cH:10][cH:11][n:12]2)[CH2:19][CH2:18]1.O[c:3]1[cH:2][cH:1][cH:28][c:21]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[cH:20]1>>[cH:1]1[cH:2][c:3]([O:4][CH2:5][CH2:6][O:7][c:8]2[n:9][cH:10][cH:11][n:12][c:13]2[N:14]2[CH2:15][CH2:1... | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.Oc1cccc(N2CCOCC2)c1 | c1cc(OCCOc2nccnc2N2CCNCC2)cc(N2CCOCC2)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | a8dd3a58be40a0309e64757d4a016d2ed6f06fd81cb30c2a6b4126270bb7933f | b0f0b3b5378653ea91e6fef29b9a760b125d67e9695c46e32b9093a79f821980 | c1cc(OCCOc2nccnc2N2CCNCC2)cc(N2CCOCC2)c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[C:7]-[C:8]-[OH;D1;+0:9].O-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[C:7]-[C:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14] | 10.5 | [{"value": 10.0, "product": "N1(CCNCC1)C=1C(=NC=CN1)OCCOC1=CC(=CC=C1)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.5, "product": "N1(CCNCC1)C=1C(=NC=CN1)OCCOC1=CC(=CC=C1)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | 1,1′-Azobis(N,N-dimethylformamide) (TMAD; 256 mg, 1.50 mmol) was added to a solution of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol (400 mg, 1.24 mmol; prepared in Example 52, Step 2), 3-(4-morpholinyl)phenol (441 mg, 1.23 mmol) and triphenylphosphine (646 mg, 2.46 mmol) in THF (3 mL). The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Primary alcohol.Aromatic alcohol.Boc | Ether.Secondary amine | C1C[NH]CC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CCN1 | c1ccccc1.c1cnccn1.C1C[NH]CCN1.C1COCC[NH]1 | HO- | C1CCOC1 | null | 2.5 | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.Oc1cccc(N2CCOCC2)c1>C1CCOC1>c1cc(OCCOc2nccnc2N2CCNCC2)cc(N2CCOCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-406ba4e901ea48fcb9536dafdbb44635 | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.Oc1c(F)cccc1F>>Fc1cccc(F)c1OCCOc1nccnc1N1CCNCC1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(=NC=CN1)OCCO.FC1=C(C(=CC=C1)F)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.CN(C)C(=O)/N=N/C(=O)N(C)C>>N1(CCNCC1)C=1C(=NC=CN1)OCCOC1=C(C=CC=C1F)F | CC(C)(C)OC(=O)[N:22]1[CH2:21][CH2:20][N:19]([c:18]2[c:13]([O:12][CH2:11][CH2:10]O)[n:14][cH:15][cH:16][n:17]2)[CH2:24][CH2:23]1.[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([F:7])[c:8]1[OH:9]>>[F:1][c:2]1[cH:3][cH:4][cH:5][c:6]([F:7])[c:8]1[O:9][CH2:10][CH2:11][O:12][c:13]1[n:14][cH:15][cH:16][n:17][c:18]1[N:19]1[CH2:20][CH2:21]... | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.Oc1c(F)cccc1F | Fc1cccc(F)c1OCCOc1nccnc1N1CCNCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c5ac0a953bd50ad6bbff24e5244495f1a91e36c5f9c02a4b443b397f6d418f9b | b0f0b3b5378653ea91e6fef29b9a760b125d67e9695c46e32b9093a79f821980 | c1ccc(OCCOc2nccnc2N2CCNCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.O-[CH2;D2;+0:7]-[C:8]-[#8:9].[OH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[#8:9]-[C:8]-[CH2;D2;+0:7]-[O;H0;D2;+0:10]-[c:11](:[c:12]):[c:13] | 45 | [{"value": 45.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared according to the procedure of Example 77 starting from 2,6-difluorophenol (239 mg, 1.84 mmol), TMAD (384 mg, 2.25 mmol), 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol (600 mg, 1.86 mmol; prepared in Example 52, Step 2), and triphenylphosphine (969 mg, 3.69 mmol) to gi... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Primary alcohol.Aromatic alcohol.Boc | Ether.Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.c1cnccn1.C1C[NH]CCN1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.Oc1c(F)cccc1F>>Fc1cccc(F)c1OCCOc1nccnc1N1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-76743798522c4873b8d0ec064b4b88d7 | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.Oc1cccc2nsnc12>>CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCOc2cccc3nsnc23)CC1 | CCOC(=O)/N=N/C(=O)OCC.C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(=NC=CN1)OCCO.OC1=CC=CC2=NSN=C21.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3>>N=1SN=C2C1C=CC=C2OCCOC=2C(=NC=CN2)N2CCN(CC2)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[n:13][cH:14][cH:15][n:16][c:17]2[O:18][CH2:19][CH2:20][OH:21])[CH2:31][CH2:32]1.O[c:22]1[cH:23][cH:24][cH:25][c:26]2[n:27][s:28][n:29][c:30]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[n:13][cH... | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.Oc1cccc2nsnc12 | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCOc2cccc3nsnc23)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | a7f9428e01551d995760c412c2c227988f0019efccda4e4034f198d009a44b00 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1cc(OCCOc2nccnc2N2CCNCC2)c2nsnc2c1 | O-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[#16;a:7]:[#7;a:8]:[c:9]:2:1.[C:10]-[C:11]-[OH;D1;+0:12]>>[C:10]-[C:11]-[O;H0;D2;+0:12]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#7;a:6]:[#16;a:7]:[#7;a:8]:[c:9]:2:1 | 12 | [{"value": 12.0, "product": "N=1SN=C2C1C=CC=C2OCCOC=2C(=NC=CN2)N2CCN(CC2)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | DEAD (0.52 mL, 3.3 mmol) was added to a slurry of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol (1.00 g, 3.08 mmol; prepared in Example 52, Step 2), 4-hydroxy-2,1,3-benzothiadiazole*(0.46 g, 3.0 mmol) and resin bound PPh3 (1.1 g, 3.3 mmol) and shaken until HPLC showed no starting material. The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccc2nsnc2c1 | c1ccc2nsnc2c1 | C1C[NH]CC[NH]1.c1cnccn1.c1ccc2nsnc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.Oc1cccc2nsnc12>>CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCOc2cccc3nsnc23)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4c591e7af8894b2abeb80c7805183da5 | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.Oc1cccc2nccnc12>>c1cc(OCCOc2nccnc2N2CCNCC2)c2nccnc2c1 | CN(C)C(=O)/N=N/C(=O)N(C)C.C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(=NC=CN1)OCCO.OC1=C2N=CC=NC2=CC=C1.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl>>Cl.N1(CCNCC1)C=1C(=NC=CN1)OCCOC1=C2N=CC=NC2=CC=C1 | CC(C)(C)OC(=O)[N:18]1[CH2:17][CH2:16][N:15]([c:14]2[c:9]([O:8][CH2:7][CH2:6][OH:5])[n:10][cH:11][cH:12][n:13]2)[CH2:20][CH2:19]1.O[c:27]1[cH:2][cH:3][cH:4][c:21]2[n:22][cH:23][cH:24][n:25][c:26]21>>[cH:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][O:8][c:9]2[n:10][cH:11][cH:12][n:13][c:14]2[N:15]2[CH2:16][CH2:17][NH:18][CH2:19][C... | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.Oc1cccc2nccnc12 | c1cc(OCCOc2nccnc2N2CCNCC2)c2nccnc2c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 3bb0987febc3469f839c54567660ec63551307069e5597e4a5e4d6cb3b251a45 | b0f0b3b5378653ea91e6fef29b9a760b125d67e9695c46e32b9093a79f821980 | c1cc(OCCOc2nccnc2N2CCNCC2)c2nccnc2c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[C:7]-[C:8]-[OH;D1;+0:9].O-[c;H0;D3;+0:10]1:[c:11]:[c:12]:[cH;D2;+0:13]:[c:14]2:[#7;a:15]:[c:16]:[c:17]:[#7;a:18]:[c:19]:2:1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[C:7]-[C:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:13]1:[c:12]:[c:11]:[cH;D2;+0:10]:[c:19]... | 76 | [{"value": 76.0, "product": "Cl.N1(CCNCC1)C=1C(=NC=CN1)OCCOC1=C2N=CC=NC2=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 2 | HOUR | TMAD (0.55 g, 3.20 mmol) was added to a stirred solution of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol (1.00 g, 3.08 mmol; prepared in Example 52, Step 2), 5-hydroxyquinoxaline*(0.45 g, 3.08 mmol) and PPh3 (0.85 g, 3.24 mmol) in THF (20 mL). The reaction was stirred at room temperature for 1.5 h ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Primary alcohol.Aromatic alcohol.Boc | Ether.Secondary amine | C1C[NH]CC[NH]1.c1ccc2nccnc2c1 | C1C[NH]CCN1.c1ccc2nccnc2c1 | c1cnccn1.C1C[NH]CCN1.c1ccc2nccnc2c1 | HO- | C1CCOC1 | 65 | 2 | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.Oc1cccc2nccnc12>C1CCOC1>c1cc(OCCOc2nccnc2N2CCNCC2)c2nccnc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fe69d702d97e4e9aae842bf78323d594 | CC(=O)c1cc2cccc(O)c2o1.CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1>>CC(=O)c1cc2cccc(OCCOc3nccnc3N3CCNCC3)c2o1 | CCOC(=O)/N=N/C(=O)OCC.C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(=NC=CN1)OCCO.C(C)(=O)C=1OC2=C(C1)C=CC=C2O.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.Cl.[NH+]1=CC=CC=C1>>Cl.N1(CCNCC1)C=1C(=NC=CN1)OCCOC1=CC=CC=2C=C(OC21)C(C)=O | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([OH:11])[c:27]2[o:28]1.CC(C)(C)OC(=O)[N:24]1[CH2:23][CH2:22][N:21]([c:20]2[c:15]([O:14][CH2:13][CH2:12]O)[n:16][cH:17][cH:18][n:19]2)[CH2:26][CH2:25]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][O:14][c:15]3[n:16][... | CC(=O)c1cc2cccc(O)c2o1.CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1 | CC(=O)c1cc2cccc(OCCOc3nccnc3N3CCNCC3)c2o1 | null | null | O.CO.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | c5ac0a953bd50ad6bbff24e5244495f1a91e36c5f9c02a4b443b397f6d418f9b | b0f0b3b5378653ea91e6fef29b9a760b125d67e9695c46e32b9093a79f821980 | c1cc(OCCOc2nccnc2N2CCNCC2)c2occc2c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.O-[CH2;D2;+0:7]-[C:8]-[#8:9].[C;D1;H3:10]-[C:11](=[O;D1;H0:12])-[c:13]:[#8;a:14]:[c:15](:[c:16]):[c:17](-[OH;D1;+0:18]):[c:19]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[#8:9]-[C:8]-[CH2;D2;+0:7]-[O;H0;D2;+0:18]-[c:17](:[c:19]):[c:15](:[c:16]):[... | 99.2 | [{"value": 14.0, "product": "Cl.N1(CCNCC1)C=1C(=NC=CN1)OCCOC1=CC=CC=2C=C(OC21)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.2, "product": "Cl.N1(CCNCC1)C=1C(=NC=CN1)OCCOC1=CC=CC=2C=C(OC21)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | DEAD (0.787 mL, 5.00 mmol) was added to a stirred solution of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol (1.50 g, 4.63 mmol; prepared in Example 52, Step 2), 2-acetyl-7-hydroxybenzofuran (0.88 g, 5.0 mmol) and PPh3 (1.31 g, 5.0 mmol) in THF (3 mL) under gentle heating. After being stirred for 30 ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Primary alcohol.Aromatic alcohol.Boc | Ether.Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccc2occc2c1.c1cnccn1.C1C[NH]CCN1 | HO- | O.CO.C1CCOC1 | null | 0.5 | CC(=O)c1cc2cccc(O)c2o1.CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1>O.CO.C1CCOC1>CC(=O)c1cc2cccc(OCCOc3nccnc3N3CCNCC3)c2o1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d11e796a7b4741938d6abf09ee61c903 | C1CNCCN1.Clc1nccnc1Cl>>Clc1nccnc1N1CCNCC1 | ClC1=NC=CN=C1Cl.N1CCNCC1.C(=O)([O-])[O-].[K+].[K+]>>ClC1=NC=CN=C1N1CCNCC1 | [NH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1.Cl[c:7]1[c:2]([Cl:1])[n:3][cH:4][cH:5][n:6]1>>[Cl:1][c:2]1[n:3][cH:4][cH:5][n:6][c:7]1[N:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1 | C1CNCCN1.Clc1nccnc1Cl | Clc1nccnc1N1CCNCC1 | null | null | C(C)#N.C(Cl)Cl | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 76b5a96b5c73afc00c162a6d1bfbc74a19ffca41d4e87b05da47a491d82e0c1f | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cnc(N2CCNCC2)cn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[Cl;D1;H0:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:12]-[C:13]-[#7:8]-[C:9]-[C:10]-1 | 69 | [{"value": 69.0, "product": "ClC1=NC=CN=C1N1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.7, "product": "ClC1=NC=CN=C1N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 1.25 | HOUR | A mixture of 2,3-dichloropyrazine (1.35 g, 15.32 mmol), piperazine (2.34 g, 27.2 mmol) and K2CO3 (1.25 g, 9.04 mmol) in acetonitrile (5.5 mL) was stirred at 110° C. for 1.25 h in a sealed tube. The reaction mixture was diluted with CH2Cl2, filtered, and concentrated to give a yellowish semisolid residue which was purif... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cnccn1 | c1cnccn1.C1C[NH]CCN1 | c1cnccn1.C1C[NH]CCN1 | HCl | C(C)#N.C(Cl)Cl | 110 | 1.25 | C1CNCCN1.Clc1nccnc1Cl>C(C)#N.C(Cl)Cl>Clc1nccnc1N1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a9ab22bf63e0436fb88454817f0f1a67 | Clc1nccnc1N1CCNCC1.OCCCOc1ccccc1>>Cl.Cl.c1ccc(OCCCOc2nccnc2N2CCNCC2)cc1 | ClC1=NC=CN=C1N1CCNCC1.O(C1=CC=CC=C1)CCCO.O([K])C(C)(C)C>>Cl.Cl.N1(CCNCC1)C=1C(=NC=CN1)OCCCOC1=CC=CC=C1 | [Cl:1][c:12]1[n:13][cH:14][cH:15][n:16][c:17]1[N:18]1[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]1.[cH:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][OH:11])[cH:24][cH:25]1>>[ClH:1].[ClH:2].[cH:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][CH2:10][O:11][c:12]2[n:13][cH:14][cH:15][n:16][c:17]2[N:18]2[CH2:19][CH2:20][NH:21][CH2:... | Clc1nccnc1N1CCNCC1.OCCCOc1ccccc1 | Cl.Cl.c1ccc(OCCCOc2nccnc2N2CCNCC2)cc1 | null | null | O1CCOCC1 | Functional Group Addition | Williamson Ether Synthesis | de1e98f41203632e2fc67ca29856eabed50edcb989a304c6e04c77f00f24f231 | 4ad4c61fbf3ad1d1545066bcc43dae0a456cfc02ae41ef8cd3196d2aa17ab829 | c1ccc(OCCCOc2nccnc2N2CCNCC2)cc1 | [#7:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:[c;H0;D3;+0:7]:1-[Cl;H0;D1;+0:8].[C:9]-[C:10]-[OH;D1;+0:11]>>[#7:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:[c;H0;D3;+0:7]:1-[O;H0;D2;+0:11]-[C:10]-[C:9].[ClH;D0;+0:8] | null | [] | 95 | CELSIUS | 6 | HOUR | 2-Chloro-3-(1-piperazinyl)pyrazine (608 mg, 3.1 mmol; from Step 1 above) and 3-phenoxypropanol (570 mg, 3.7 mmol) was dissolved in dioxane (10 mL). KO-t-Bu (870 mg, 7.7 mmol) was added and the mixture was stirred at 95° C. for 6 h. The solvent was evaporated and the residue was purified by chromatography on silica gel ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cnccn1 | c1cnccn1 | c1ccccc1.c1cnccn1.C1C[NH]CCN1 | Other | O1CCOCC1 | 95 | 6 | Clc1nccnc1N1CCNCC1.OCCCOc1ccccc1>O1CCOCC1>Cl.Cl.c1ccc(OCCCOc2nccnc2N2CCNCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-210ae9ffb2e041219ef55f98f29082f9 | O=C1OCCO1.Oc1ccccc1C(F)(F)F>>OCCOc1ccccc1C(F)(F)F | FC(C1=C(C=CC=C1)O)(F)F.C(=O)([O-])[O-].[K+].[K+].C1(OCCO1)=O>>FC(C1=C(OCCO)C=CC=C1)(F)F | O=C1O[CH2:3][CH2:2][O:1]1.[OH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11]([F:12])([F:13])[F:14]>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[C:11]([F:12])([F:13])[F:14] | O=C1OCCO1.Oc1ccccc1C(F)(F)F | OCCOc1ccccc1C(F)(F)F | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 34950df4dc1bc6c778d9cfa26c728e443e4886f7382a4283f1fbae4a959b8c37 | c6f5c5ba2d936b513bc18d6bcb095f40591aa3ba8700a9f5b8ecbbdd690dab72 | c1ccccc1 | O=C1-O-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[OH;D1;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 20 | [{"value": 20.0, "product": "FC(C1=C(OCCO)C=CC=C1)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 19.7, "product": "FC(C1=C(OCCO)C=CC=C1)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | A mixture of 2-trifluoromethylphenol (2.00 g, 12.3 mmol), K2CO3 (1.71 g, 12.3 mmol) and ethylene carbonate (1.20 g, 13.6 mmol) in dry DMF (30 mL) was heated at 150° C. for 1 h. After cooling, the reaction was quenched by addition of water (10 mL). The mixture was concentrated in vacuo and the residue partitioned betwee... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Aromatic alcohol | Ether.Primary alcohol | C1COCO1 | null | c1ccccc1 | Other | CN(C)C=O | 150 | null | O=C1OCCO1.Oc1ccccc1C(F)(F)F>CN(C)C=O>OCCOc1ccccc1C(F)(F)F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c267f725b5b74ac69532be19c367e0e2 | CO.Cc1ccc(S(=O)(=O)O)cc1.O=Cc1cccc(OCCO)c1>>COC(OC)c1cccc(OCCO)c1 | CC=1C=CC(=CC1)S(=O)(=O)O.OCCOC=1C=C(C=O)C=CC1.CO.CC=1C=CC(=CC1)S(=O)(=O)O>>COC(C=1C=C(OCCO)C=CC1)OC | [CH3:1][OH:2].O=S(=O)(O)c1ccc([CH3:5])cc1.[CH:3](=[O:4])[c:6]1[cH:7][cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][OH:14])[cH:15]1>>[CH3:1][O:2][CH:3]([O:4][CH3:5])[c:6]1[cH:7][cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][OH:14])[cH:15]1 | CO.Cc1ccc(S(=O)(=O)O)cc1.O=Cc1cccc(OCCO)c1 | COC(OC)c1cccc(OCCO)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 40a7f05c53d7697f2819723c06141de2ce431fc9d84b5e2240cb10496c3c3fdd | 72d11f04e08896b2743150165f68c1a0ab90530b74d79b146a0ee5ddc1e5f249 | c1ccccc1 | O-S(=O)(=O)-c1:c:c:c(-[CH3;D1;+0:1]):c:c:1.[C;D1;H3:2]-[OH;D1;+0:3].[O;H0;D1;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[O;H0;D2;+0:3]-[CH;D3;+0:5](-[O;H0;D2;+0:4]-[CH3;D1;+0:1])-[c:6](:[c:7]):[c:8] | null | [] | null | null | 23 | HOUR | p-TsOH (165 mg, 0.87 mmol) was added to a solution of the product obtained in Step 1 (1.45 g, 8.73 mmol) in dry MeOH (60 mL). After being stirred for 23 h at room temperature, more p-TsOH (170 mg, 0.89 mmol) was added. After additional 4 h of stirring, the reaction was quenched by the addition of NaHCO3 (saturated aque... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Aldehyde.Methanol | Ether.Ether | c1ccccc1 | null | c1ccccc1 | TsOH.HO- | null | null | 23 | CO.Cc1ccc(S(=O)(=O)O)cc1.O=Cc1cccc(OCCO)c1>>COC(OC)c1cccc(OCCO)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-52e4b5815c4948f394927bfebd82e2b9 | O=C1OCCO1.Oc1cc(F)cc(F)c1>>OCCOc1cc(F)cc(F)c1 | FC=1C=C(C=C(C1)F)O.C1(OCCO1)=O.[H-].[Na+]>>FC=1C=C(OCCO)C=C(C1)F | O=C1O[CH2:3][CH2:2][O:1]1.[OH:4][c:5]1[cH:6][c:7]([F:8])[cH:9][c:10]([F:11])[cH:12]1>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][c:7]([F:8])[cH:9][c:10]([F:11])[cH:12]1 | O=C1OCCO1.Oc1cc(F)cc(F)c1 | OCCOc1cc(F)cc(F)c1 | null | null | C1(=CC=CC=C1)C.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 34950df4dc1bc6c778d9cfa26c728e443e4886f7382a4283f1fbae4a959b8c37 | c6f5c5ba2d936b513bc18d6bcb095f40591aa3ba8700a9f5b8ecbbdd690dab72 | c1ccccc1 | O=C1-O-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[OH;D1;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | In a sealed Pyrex tube, a mixture of 3,5-difluorophenol (2.19 g, 16.8 mmol), ethylene carbonate (1.0 g, 11.4 mmol), a catalytic amount of NaH (60% in mineral oil) in DMF (1 mL) was reacted in a Labwell MW-10 microwave reactor at 50 W for 3 min. The reaction mixture was diluted with toluene and washed with 5% aqueous Na... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Aromatic alcohol | Ether.Primary alcohol | C1COCO1 | null | c1ccccc1 | Other | C1(=CC=CC=C1)C.CN(C)C=O | null | null | O=C1OCCO1.Oc1cc(F)cc(F)c1>C1(=CC=CC=C1)C.CN(C)C=O>OCCOc1cc(F)cc(F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e18f3809ac8644f1a2aa1e01f217bbeb | O=C1OCCO1.Oc1ccc2c(c1)OCO2>>OCCOc1ccc2c(c1)OCO2 | C1OC2=C(O1)C=C(C=C2)O.C1(OCCO1)=O>>O1COC2=C1C=CC(=C2)OCCO | O=C1O[CH2:3][CH2:2][O:1]1.[OH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][O:13]2>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH2:12][O:13]2 | O=C1OCCO1.Oc1ccc2c(c1)OCO2 | OCCOc1ccc2c(c1)OCO2 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 34950df4dc1bc6c778d9cfa26c728e443e4886f7382a4283f1fbae4a959b8c37 | c6f5c5ba2d936b513bc18d6bcb095f40591aa3ba8700a9f5b8ecbbdd690dab72 | c1ccc2c(c1)OCO2 | O=C1-O-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[OH;D1;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 99 | [{"value": 99.0, "product": "O1COC2=C1C=CC(=C2)OCCO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared according to the procedure of Example 114, Step 1 starting from sesamol (2.0 g, 14.5 mmol) and ethylene carbonate (1.0 g, 11.4 mmol): solid; yield 99%. MS m/z 182 (M)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Aromatic alcohol | Ether.Primary alcohol | C1COCO1 | null | c1ccc2c(c1)OCO2 | Other | null | null | null | O=C1OCCO1.Oc1ccc2c(c1)OCO2>>OCCOc1ccc2c(c1)OCO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-055a93d19a634fb3bc2edc6394ee33e8 | CCCCOc1cccc(O)c1.O=C1OCCO1>>CCCCOc1cccc(OCCO)c1 | C(CCC)OC=1C=C(C=CC1)O.C1(OCCO1)=O>>C(CCC)OC=1C=C(OCCO)C=CC1 | [CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([OH:11])[cH:15]1.O=C1O[CH2:12][CH2:13][O:14]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][OH:14])[cH:15]1 | CCCCOc1cccc(O)c1.O=C1OCCO1 | CCCCOc1cccc(OCCO)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 34950df4dc1bc6c778d9cfa26c728e443e4886f7382a4283f1fbae4a959b8c37 | c6f5c5ba2d936b513bc18d6bcb095f40591aa3ba8700a9f5b8ecbbdd690dab72 | c1ccccc1 | O=C1-O-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[OH;D1;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 85 | [{"value": 85.0, "product": "C(CCC)OC=1C=C(OCCO)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compund was prepared according to the procedure of Example 114, Step 1 starting from 3-n-butoxyphenol (2.0 g, 12 mmol) and ethylene carbonate (0.88 g, 10 mmol). Oil; yield 85%. MS m/z 210 (M)+.
Conditions: See reaction.notes.procedure_details.
Workup: The title compund was prepared | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Aromatic alcohol | Ether.Primary alcohol | C1COCO1 | null | c1ccccc1 | Other | null | null | null | CCCCOc1cccc(O)c1.O=C1OCCO1>>CCCCOc1cccc(OCCO)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-736f4940698043c6bc8cd5e9d9295cd0 | O=C1OCCO1.Oc1cccc(C(F)(F)F)c1>>OCCOc1cccc(C(F)(F)F)c1 | FC(C=1C=C(C=CC1)O)(F)F.C1(OCCO1)=O>>FC(C=1C=C(OCCO)C=CC1)(F)F | O=C1O[CH2:3][CH2:2][O:1]1.[OH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14]1 | O=C1OCCO1.Oc1cccc(C(F)(F)F)c1 | OCCOc1cccc(C(F)(F)F)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 34950df4dc1bc6c778d9cfa26c728e443e4886f7382a4283f1fbae4a959b8c37 | c6f5c5ba2d936b513bc18d6bcb095f40591aa3ba8700a9f5b8ecbbdd690dab72 | c1ccccc1 | O=C1-O-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[OH;D1;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 64 | [{"value": 64.0, "product": "FC(C=1C=C(OCCO)C=CC1)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared according to the procedure of Example 114, Step 1 starting from 3-trifluoromethylphenol (3.89 g, 24 mmol) and ethylene carbonate (1.76 g, 20 mmol) with the exception that no DMF was used. Oil; yield 64%. MS m/z 206 (M)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Aromatic alcohol | Ether.Primary alcohol | C1COCO1 | null | c1ccccc1 | Other | CN(C)C=O | null | null | O=C1OCCO1.Oc1cccc(C(F)(F)F)c1>CN(C)C=O>OCCOc1cccc(C(F)(F)F)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-516a8a78ef0a416396804c4ce011e1f4 | O=C1OCCO1.Oc1cccc(-c2ccccc2)c1>>OCCOc1cccc(-c2ccccc2)c1 | C1(=CC=CC=C1)C=1C=C(C=CC1)O.C1(OCCO1)=O>>C1(=CC=CC=C1)C=1C=C(OCCO)C=CC1 | O=C1O[CH2:3][CH2:2][O:1]1.[OH:4][c:5]1[cH:6][cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16]1>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16]1 | O=C1OCCO1.Oc1cccc(-c2ccccc2)c1 | OCCOc1cccc(-c2ccccc2)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 34950df4dc1bc6c778d9cfa26c728e443e4886f7382a4283f1fbae4a959b8c37 | c6f5c5ba2d936b513bc18d6bcb095f40591aa3ba8700a9f5b8ecbbdd690dab72 | c1ccc(-c2ccccc2)cc1 | O=C1-O-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[OH;D1;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 86 | [{"value": 86.0, "product": "C1(=CC=CC=C1)C=1C=C(OCCO)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared according to the procedure of Example 114, Step 1 starting, from 3-phenylphenol (1.72 g, 0.1 mmol) and ethylene carbonate (0.80 g, 9.1 mmol) and DMF (3 mL). Semi-solid; yield 86%. MS m/z 214 (M)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Aromatic alcohol | Ether.Primary alcohol | C1COCO1 | null | c1ccccc1.c1ccccc1 | Other | CN(C)C=O | null | null | O=C1OCCO1.Oc1cccc(-c2ccccc2)c1>CN(C)C=O>OCCOc1cccc(-c2ccccc2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8e121cbe1c3844068436c6287637441a | CC(=O)Nc1cccc(O)c1.O=C1OCCO1>>CC(=O)Nc1cccc(OCCO)c1 | C(C)(=O)NC=1C=C(C=CC1)O.C1(OCCO1)=O>>C(C)(=O)NC=1C=C(OCCO)C=CC1 | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([OH:10])[cH:14]1.O=C1O[CH2:11][CH2:12][O:13]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][OH:13])[cH:14]1 | CC(=O)Nc1cccc(O)c1.O=C1OCCO1 | CC(=O)Nc1cccc(OCCO)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 34950df4dc1bc6c778d9cfa26c728e443e4886f7382a4283f1fbae4a959b8c37 | c6f5c5ba2d936b513bc18d6bcb095f40591aa3ba8700a9f5b8ecbbdd690dab72 | c1ccccc1 | O=C1-O-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[OH;D1;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 99 | [{"value": 99.0, "product": "C(C)(=O)NC=1C=C(OCCO)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title product was prepared according to the procedure described in Example 114, Step 1, starting from 3-acetamidophenol (2.10 g, 13.9 mmol) and ethylene carbonate (0.88 g, 10 mmol). The crude product was purified by column chromatography on silica using toluene/EtOAc/MeOH (49:49:2). Oil; yield 99%. MS m/z 195 (M)+.... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Aromatic alcohol | Ether.Primary alcohol | C1COCO1 | null | c1ccccc1 | Other | null | null | null | CC(=O)Nc1cccc(O)c1.O=C1OCCO1>>CC(=O)Nc1cccc(OCCO)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dfa5a9f86d104aa7b0056983f1da7d66 | O=C1OCCO1.Oc1cccc2cnccc12>>OCCOc1cccc2cnccc12 | OC1=C2C=CN=CC2=CC=C1.C1(OCCO1)=O.C(=O)([O-])[O-].[K+].[K+]>>C1=NC=CC2=C(C=CC=C12)OCCO | O=C1O[CH2:3][CH2:2][O:1]1.[OH:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[cH:10][n:11][cH:12][cH:13][c:14]12>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[cH:10][n:11][cH:12][cH:13][c:14]12 | O=C1OCCO1.Oc1cccc2cnccc12 | OCCOc1cccc2cnccc12 | null | null | C(Cl)(Cl)Cl.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 34950df4dc1bc6c778d9cfa26c728e443e4886f7382a4283f1fbae4a959b8c37 | c6f5c5ba2d936b513bc18d6bcb095f40591aa3ba8700a9f5b8ecbbdd690dab72 | c1ccc2cnccc2c1 | O=C1-O-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[OH;D1;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 67.5 | [{"value": 67.0, "product": "C1=NC=CC2=C(C=CC=C12)OCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.5, "product": "C1=NC=CC2=C(C=CC=C12)OCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 155 | CELSIUS | null | null | A mixture of 5-hydroxyisoquinoline (2.05 g, 14.1 mmol), ethylene carbonate (1.43 g, 16.2 mmol), K2CO3 (0.97 g, 7.1 mmol) in DMF (6 mL) was heated at 155° C. for 1.5 h under stirring in a sealed tube. After cooling, the mixture was diluted with CHCl3 and filtered through a pad of Celite. The brownish filtrate was concen... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Aromatic alcohol | Ether.Primary alcohol | C1COCO1 | null | c1ccc2cnccc2c1 | Other | C(Cl)(Cl)Cl.CN(C)C=O | 155 | null | O=C1OCCO1.Oc1cccc2cnccc12>C(Cl)(Cl)Cl.CN(C)C=O>OCCOc1cccc2cnccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-da1d7b8170e442d9bc8659e5dd32698f | C1CO1.Oc1cccc2cc[nH]c12>>OCCOc1cccc2cc[nH]c12 | O.OC=1C=CC=C2C=CNC12.C1CO1.[H-].[Na+]>>N1C=CC2=CC=CC(=C12)OCCO | [O:1]1[CH2:2][CH2:3]1.[OH:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[cH:10][cH:11][nH:12][c:13]12>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[cH:10][cH:11][nH:12][c:13]12 | C1CO1.Oc1cccc2cc[nH]c12 | OCCOc1cccc2cc[nH]c12 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 2f3af25ad636dccf6d6b7b47abd80baf01c2c1706fea7bd73a2e640d18ec6f42 | 4dec6f037b05de3f6420849dd52106666be8664a0b8fc895dcf197e624c15254 | c1ccc2[nH]ccc2c1 | [C:1]1-[CH2;D2;+0:2]-[O;H0;D2;+0:3]-1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7](:[c:8]):[#7;a:9]:[c:10]>>[OH;D1;+0:3]-[C:1]-[CH2;D2;+0:2]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7](:[c:8]):[#7;a:9]:[c:10] | 34 | [{"value": 34.0, "product": "N1C=CC2=CC=CC(=C12)OCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.9, "product": "N1C=CC2=CC=CC(=C12)OCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 5 | DAY | A mixture of 7-hydroxyindole (1.00 g, 7.51 mmol) and ethylene oxide (0.33 g, 7.50 mmol) in dioxane (3 mL) was placed in a reaction tube. NaH (60% in oil; 0.100 g, 2.45 mmol) was added and the reaction mixture was stirred at 100° C. for 5 days. The reaction mixture was poured into water, extracted with EtOAc, dried (MgS... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Aromatic alcohol | Ether.Primary alcohol | C1CO1 | null | c1ccc2[nH]ccc2c1 | null | O1CCOCC1 | 100 | 120 | C1CO1.Oc1cccc2cc[nH]c12>O1CCOCC1>OCCOc1cccc2cc[nH]c12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-743032464a5c4d2ebceae7a7c7f36f3a | O=C1OCCO1.Oc1ccc2cc[nH]c2c1>>OCCOc1ccc2cc[nH]c2c1 | C1(OCCO1)=O.OC1=CC=C2C=CNC2=C1.C(=O)([O-])[O-].[K+].[K+]>>N1C=CC2=CC=C(C=C12)OCCO | O=C1O[CH2:3][CH2:2][O:1]1.[OH:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][nH:11][c:12]2[cH:13]1>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][nH:11][c:12]2[cH:13]1 | O=C1OCCO1.Oc1ccc2cc[nH]c2c1 | OCCOc1ccc2cc[nH]c2c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 34950df4dc1bc6c778d9cfa26c728e443e4886f7382a4283f1fbae4a959b8c37 | c6f5c5ba2d936b513bc18d6bcb095f40591aa3ba8700a9f5b8ecbbdd690dab72 | c1ccc2[nH]ccc2c1 | O=C1-O-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1.[#7;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#7;a:4]:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3]):[c:9] | null | [] | 125 | CELSIUS | null | null | A mixture of 6-hydroxyindole (2.66 g, 20 mmol) and K2CO3 (3.04 g, 22 mmol) was stirred in DMF (10 mL) at 80° C. for 10 min. A solution of ethylene carbonate (1.94 g, 22 mmol) in DMF (4 mL) was added and the mixture was heated at 125° C. for 3 h. The mixture was concentrated, diluted with water, and extracted with tolue... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Aromatic alcohol | Ether.Primary alcohol | C1COCO1 | null | c1ccc2[nH]ccc2c1 | Other | CN(C)C=O | 125 | null | O=C1OCCO1.Oc1ccc2cc[nH]c2c1>CN(C)C=O>OCCOc1ccc2cc[nH]c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8b94bdbb09c74fa7bcbd2c63cdf905eb | CC(=O)OC(C)=O.Nc1ccc2c(c1)OC(CO)CO2>>CC(=O)Nc1ccc2c(c1)OC(CO)CO2 | C(C)(=O)OC(C)=O.C(C)(=O)OC(C)=O.NC=1C=CC2=C(OC(CO2)CO)C1.CCN(CC)CC>>C(C)(=O)NC=1C=CC2=C(OC(CO2)CO)C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH:12]([CH2:13][OH:14])[CH2:15][O:16]2>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[c:9]([cH:10]1)[O:11][CH:12]([CH2:13][OH:14])[CH2:15][O:16]2 | CC(=O)OC(C)=O.Nc1ccc2c(c1)OC(CO)CO2 | CC(=O)Nc1ccc2c(c1)OC(CO)CO2 | null | null | C(Cl)Cl | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | c1ccc2c(c1)OCCO2 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | 46 | [{"value": 46.0, "product": "C(C)(=O)NC=1C=CC2=C(OC(CO2)CO)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | Acetic anhydride (0.24 g, 2.4 mmol) was added to a stirred mixture of the title compound from Step 1 above (0.30 g, 1.66 mmol) and Et3N (0.70 g, 6.9 mmol) in CH2Cl2(30 mL). The reaction was stirred at room temperature for 15 h. More acetic anhydride (0.10 g, 1.0 mmol) was added and the mixture was stirred for a further... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | c1ccc2c(c1)OCCO2 | HO- | C(Cl)Cl | null | 15 | CC(=O)OC(C)=O.Nc1ccc2c(c1)OC(CO)CO2>C(Cl)Cl>CC(=O)Nc1ccc2c(c1)OC(CO)CO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a562681c19a441419ac5e98241e7db05 | OCCCl.Oc1cccnc1>>OCCOc1cccnc1 | OC=1C=NC=CC1.ClCCO.C(=O)([O-])[O-].[K+].[K+]>>N1=CC(=CC=C1)OCCO | Cl[CH2:3][CH2:2][OH:1].[OH:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1 | OCCCl.Oc1cccnc1 | OCCOc1cccnc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccncc1 | Cl-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9]>>[O;D1;H1:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]:[#7;a:8]:[c:9] | 19 | [{"value": 19.0, "product": "N1=CC(=CC=C1)OCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 18.8, "product": "N1=CC(=CC=C1)OCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | 3 | HOUR | A mixture of 3-hydroxypyridine (2.00 g, 21 mmol), 2-chloroethanol (1.69 g, 21 mmol) and K2CO3(8.7, 63 mmol) in DMF (10 mL) was stirred at 130° C. for 3 h. After cooling, the black mixture was filtered through a short bed of alumina using acetone as eluent to afford a brown oil which was partitioned between water (30 mL... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccncc1 | HCl | CN(C)C=O | 130 | 3 | OCCCl.Oc1cccnc1>CN(C)C=O>OCCOc1cccnc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7477ad76ee114542952e74de0a9367f4 | Brc1csc2ccccc12.OCCO>>OCCOc1csc2ccccc12 | BrC1=CSC2=C1C=CC=C2.O([K])C(C)(C)C.[I-].[K+].C(CO)O>>S1C=C(C2=C1C=CC=C2)OCCO | Br[c:5]1[cH:6][s:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12.[OH:1][CH2:2][CH2:3][OH:4]>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][s:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12 | Brc1csc2ccccc12.OCCO | OCCOc1csc2ccccc12 | null | [Cu]=O | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 3e72ebf1f743aad266d615a10707517aceccc02bd66ac0d5feca1ec90c9b010d | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc2sccc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4](:[c:5]):[c:6]:1:[c:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[#16;a:3]:[c:4](:[c:5]):[c:6]:1:[c:7] | 60 | [{"value": 60.0, "product": "S1C=C(C2=C1C=CC=C2)OCCO", "details": "PERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | 24 | HOUR | A mixture of 3-bromobenzothiophene (3.00 g, 14.1 mmol), KO-t-Bu (4.74 g, 42.2 mmol), copper (II) oxide (0.56 g, 7.0 mmol) and potassium iodide (2.34 g, 14.1 mmol) in ethylene glycol (10 mL) was stirred at 140° C. for 24 h. The reaction was quenched with water (100 mL) and filtered through a pad of Celite. The water pha... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccc2sccc2c1 | c1ccc2sccc2c1 | c1ccc2sccc2c1 | HBr | [Cu]=O | 140 | 24 | Brc1csc2ccccc12.OCCO>[Cu]=O>OCCOc1csc2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1ac4601af65d4780834d083041de219d | O=C1OCCO1.Oc1cccc2ocnc12>>OCCOc1cccc2ocnc12 | C(=O)([O-])[O-].[K+].[K+].OC1=CC=CC2=C1N=CO2.C1(OCCO1)=O>>O1C=NC2=C1C=CC=C2OCCO | O=C1O[CH2:3][CH2:2][O:1]1.[OH:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[o:10][cH:11][n:12][c:13]12>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[o:10][cH:11][n:12][c:13]12 | O=C1OCCO1.Oc1cccc2ocnc12 | OCCOc1cccc2ocnc12 | null | null | CO.O.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 34950df4dc1bc6c778d9cfa26c728e443e4886f7382a4283f1fbae4a959b8c37 | c6f5c5ba2d936b513bc18d6bcb095f40591aa3ba8700a9f5b8ecbbdd690dab72 | c1ccc2ocnc2c1 | O=C1-O-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1>>[OH;D1;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7]1:[#7;a:8]:[c:9]:[#8;a:10]:[c:11]:1 | null | [] | 90 | CELSIUS | 2 | HOUR | K2CO3 (254 mg, 1.84 mmol) was added to a stirred solution of 4-hydroxybenzoxazole* (248 mg, 1.84 mmol) in DMF (5 mL) at room temperature. The mixture was heated at 90° C. for 15 min and ethylene carbonate (176 mg, 2.00 mmol) was added. The mixture was stirred at 150° C. for 2 h and allowed to attain room temperature. T... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Aromatic alcohol | Ether.Primary alcohol | C1COCO1 | null | c1ccc2ocnc2c1 | Other | CO.O.CN(C)C=O | 90 | 2 | O=C1OCCO1.Oc1cccc2ocnc12>CO.O.CN(C)C=O>OCCOc1cccc2ocnc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8d886d7fe82f49eda2a805617ff3881d | Nc1cc(O)c2ccccc2n1.OCCBr>>Nc1cc(OCCO)c2ccccc2n1 | NC1=NC2=CC=CC=C2C(=C1)O.C(=O)([O-])[O-].[K+].[K+].BrCCO>>NC1=NC2=CC=CC=C2C(=C1)OCCO | [NH2:1][c:2]1[cH:3][c:4]([OH:5])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[n:15]1.Br[CH2:6][CH2:7][OH:8]>>[NH2:1][c:2]1[cH:3][c:4]([O:5][CH2:6][CH2:7][OH:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[n:15]1 | Nc1cc(O)c2ccccc2n1.OCCBr | Nc1cc(OCCO)c2ccccc2n1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc2ncccc2c1 | Br-[CH2;D2;+0:1]-[C:2]-[O;D1;H1:3].[OH;D1;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1>>[O;D1;H1:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | null | [] | 150 | CELSIUS | 7 | HOUR | To a mixture of 2-amino-4-hydroxyquinoline (0.505 g, 3.15 mmol) and K2CO3 (0.87 g, 6.3 mmol) in DMF (10 mL) was added of 2-bromoethanol (0.470 g, 3.78 mmol). The mixture was stirred at 150° C. for 7 h. The reaction mixture was concentrated and the residue purified by column chromatography on silica using MeOH/CHCl3 (1:... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2ncccc2c1 | HBr | CN(C)C=O | 150 | 7 | Nc1cc(O)c2ccccc2n1.OCCBr>CN(C)C=O>Nc1cc(OCCO)c2ccccc2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b20654890c594786b3622f1068694c9f | CCOC(=O)C(Cl)C(=O)OCC.Nc1ncccc1O>>CCOC(=O)C1Oc2cccnc2NC1=O | ClC(C(=O)OCC)C(=O)OCC.OC=1C(=NC=CC1)N.C(C)N(CC)CC>>C(C)OC(=O)C1C(NC2=C(O1)C=CC=N2)=O | CCO[C:15]([CH:6](Cl)[C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:16].[OH:7][c:8]1[cH:9][cH:10][cH:11][n:12][c:13]1[NH2:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[O:7][c:8]2[cH:9][cH:10][cH:11][n:12][c:13]2[NH:14][C:15]1=[O:16] | CCOC(=O)C(Cl)C(=O)OCC.Nc1ncccc1O | CCOC(=O)C1Oc2cccnc2NC1=O | null | null | CCO | Acylation | OtherReaction | f7925936ddc97573dfb2a4209168e9cd73b2f01f35e03fc95cc9bff5c7e7e5ac | 614b7bc0d2537b4171b080e969b4bcdba98bd0ee7c6a01936c9e049ad937ad78 | O=C1COc2cccnc2N1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:3](-Cl)-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7].[NH2;D1;+0:8]-[c:9](:[#7;a:10]:[c:11]):[c:12](-[OH;D1;+0:13]):[c:14]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[CH;D3;+0:3]1-[O;H0;D2;+0:13]-[c:12](:[c:14]):[c:9](:[#7;a:10]:[c:11])-[NH;D2;+0:8]-[C;H0;D3;+0:1]-1=[O;D1;H0:2] | null | [] | null | null | null | null | Diethyl chloromalonate (9.73 g, 50 mmol) was added to a stirred mixture of 3-hydroxy-2-aminopyridine (5.51 g, 50 mmol), triethylamine (6.97 mL, 50 mmol) and EtOH (100 mL) at room temperature. The mixture was heated at reflux for 17 h and allowed to attain room temperature. The precipitate formed was filtered off, washe... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Ester.Ester.Aromatic alcohol.Primary amine | Ester.Ether.Secondary amide | null | c1cnc2c(c1)OCCN2 | c1cnc2c(c1)OCCN2 | HCl | CCO | null | null | CCOC(=O)C(Cl)C(=O)OCC.Nc1ncccc1O>CCO>CCOC(=O)C1Oc2cccnc2NC1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-505c56af85be4a3496e51b1ff750ab27 | CCOC(=O)C1Oc2cccnc2NC1=O>>OCC1CNc2ncccc2O1 | [OH-].[Na+].C(C)OC(=O)C1C(NC2=C(O1)C=CC=N2)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>>O1C2=C(NCC1CO)N=CC=C2 | CCO[C:2](=[O:1])[CH:3]1[C:4](=O)[NH:5][c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[O:12]1>>[OH:1][CH2:2][CH:3]1[CH2:4][NH:5][c:6]2[n:7][cH:8][cH:9][cH:10][c:11]2[O:12]1 | CCOC(=O)C1Oc2cccnc2NC1=O | OCC1CNc2ncccc2O1 | null | null | C1CCOC1 | Reduction | OtherReaction | 7a8391d510df505c54105d0f8bf47c637c83b355ffcc8b34d50cc234baf2ae53 | b2cae9b4721588c91bc86bec3768ea5e1318797d9b0e5a3847151719cf6782eb | c1cnc2c(c1)OCCN2 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]1-[#8:4]-[c:5]:[c:6](:[#7;a:7])-[#7:8]-[C;H0;D3;+0:9]-1=O>>[#7;a:7]:[c:6]1:[c:5]-[#8:4]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[CH2;D2;+0:9]-[#7:8]-1 | null | [] | 45 | CELSIUS | 30 | MINUTE | A solution of 3,4-dihydro-3-oxo-2H-pyrido[3,2-b]-1,4-oxazin-2-carboxylic acid ethyl ester (1.10 g, 5.0 mmol) in THF (50 mL) was added over 5 min to a stirred mixture of LiAlH4 (0.38 g, 10 mmol) and THF (20 mL) at 40° C. The mixture was stirred at 45° C. for 30 min and at reflux for 4 h. The mixture was allowed to attai... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide | Primary alcohol | c1cnc2c(c1)OCCN2 | c1cnc2c(c1)OCCN2 | c1cnc2c(c1)OCCN2 | Other | C1CCOC1 | 45 | 0.5 | CCOC(=O)C1Oc2cccnc2NC1=O>C1CCOC1>OCC1CNc2ncccc2O1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-da890de3566e4b029fd14d35890a3490 | C1CNCCN1.Fc1cc2nc(Cl)c(Cl)nc2cc1F>>Fc1cc2nc(Cl)c(N3CCNCC3)nc2cc1F | N1CCNCC1.FC=1C=C2N=C(C(=NC2=CC1F)Cl)Cl>>ClC1=NC2=CC(=C(C=C2N=C1N1CCNCC1)F)F | [NH:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1.Cl[c:8]1[c:6]([Cl:7])[n:5][c:4]2[cH:3][c:2]([F:1])[c:18]([F:19])[cH:17][c:16]2[n:15]1>>[F:1][c:2]1[cH:3][c:4]2[n:5][c:6]([Cl:7])[c:8]([N:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[n:15][c:16]2[cH:17][c:18]1[F:19] | C1CNCCN1.Fc1cc2nc(Cl)c(Cl)nc2cc1F | Fc1cc2nc(Cl)c(N3CCNCC3)nc2cc1F | null | null | CCO | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 678d34c35338404be7cc405e43966a4086710a7eff0ca432e8cc0a9367151dda | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2nc(N3CCNCC3)cnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[Cl;D1;H0:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | 75 | CELSIUS | null | null | Piperazine (0.86 g, 10 mmol) was added to a stirred suspension of 6,7-difluoro-2,3-dichloroquinoxaline*(1.18 g, 5 mmol) in EtOH (50 mL) at room temperature. The mixture was heated at 75° C. for 17 h, allowed to cool and filtered to give the product as a pale yellow solid: yield 0.40 g (28%); mp 294-297° C. (dec). MS m/... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccc2nccnc2c1 | c1ccc2nccnc2c1.C1C[NH]CCN1 | c1ccc2nccnc2c1.C1C[NH]CCN1 | HCl | CCO | 75 | null | C1CNCCN1.Fc1cc2nc(Cl)c(Cl)nc2cc1F>CCO>Fc1cc2nc(Cl)c(N3CCNCC3)nc2cc1F |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4f69f43ecca9417b8931c5ecd4141148 | C1CNCCN1.Clc1cc2nc(Cl)c(Cl)nc2cc1Cl>>Clc1cc2nc(Cl)c(N3CCNCC3)nc2cc1Cl | N1CCNCC1.ClC1=NC2=CC(=C(C=C2N=C1Cl)Cl)Cl>>N1(CCNCC1)C=1C(=NC2=CC(=C(C=C2N1)Cl)Cl)Cl | [NH:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1.Cl[c:8]1[c:6]([Cl:7])[n:5][c:4]2[cH:3][c:2]([Cl:1])[c:18]([Cl:19])[cH:17][c:16]2[n:15]1>>[Cl:1][c:2]1[cH:3][c:4]2[n:5][c:6]([Cl:7])[c:8]([N:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[n:15][c:16]2[cH:17][c:18]1[Cl:19] | C1CNCCN1.Clc1cc2nc(Cl)c(Cl)nc2cc1Cl | Clc1cc2nc(Cl)c(N3CCNCC3)nc2cc1Cl | null | null | CCO | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 678d34c35338404be7cc405e43966a4086710a7eff0ca432e8cc0a9367151dda | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2nc(N3CCNCC3)cnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[Cl;D1;H0:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | 8 | HOUR | Piperazine (0.69 g, 8.06 mmol) was added to a stirred suspension of 2,3,6,7-tetrachloroquinoxaline (1.08 g, 4.03 mmol) in EtOH (125 mL) at room temperature. The mixture was stirred at room temperature for 8 h and filtered to give the product as a pale yellow solid: yield 0.88 g (69%), mp>300° C. MS m/z 316/318 (M)+.
Co... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccc2nccnc2c1 | c1ccc2nccnc2c1.C1C[NH]CCN1 | c1ccc2nccnc2c1.C1C[NH]CCN1 | HCl | CCO | null | 8 | C1CNCCN1.Clc1cc2nc(Cl)c(Cl)nc2cc1Cl>CCO>Clc1cc2nc(Cl)c(N3CCNCC3)nc2cc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bf174f0c7f1e4e9caee1592ec6ddfcab | C1CNCCN1.Clc1nc2cscc2nc1Cl>>Clc1nc2cscc2nc1N1CCNCC1 | N1CCNCC1.ClC=1C(=NC=2C(N1)=CSC2)Cl>>ClC=1C(=NC=2C(N1)=CSC2)N2CCNCC2 | [NH:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1.Cl[c:10]1[c:2]([Cl:1])[n:3][c:4]2[cH:5][s:6][cH:7][c:8]2[n:9]1>>[Cl:1][c:2]1[n:3][c:4]2[cH:5][s:6][cH:7][c:8]2[n:9][c:10]1[N:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1 | C1CNCCN1.Clc1nc2cscc2nc1Cl | Clc1nc2cscc2nc1N1CCNCC1 | null | null | CCO | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 710ff5d16595cf6df4f149981de3109bf209176b07aa0a914f4d4520d696cda4 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1nc2cscc2nc1N1CCNCC1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[c:4]:[#16;a:5]:[c:6]:[c:7]:2:[#7;a:8]:[c:9]:1-[Cl;D1;H0:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[Cl;D1;H0:10]-[c:9]1:[#7;a:8]:[c:7]2:[c:6]:[#16;a:5]:[c:4]:[c:3]:2:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:14]1-[C:13]-[C:12]-[#7:11]-[C:16]-[C:15]-1 | 29.1 | [{"value": 29.0, "product": "ClC=1C(=NC=2C(N1)=CSC2)N2CCNCC2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.1, "product": "ClC=1C(=NC=2C(N1)=CSC2)N2CCNCC2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Piperazine (92 mg, 1.07 mmol) was added to a stirred suspension of 2,3-dichlorothieno[3,4-b]pyrazine (110 mg, 0.54 mmol) in EtOH (5 mL) at room temperature. The mixture was stirred at reflux for 16 h and filtered. The solid was purified by chromatography on silica gel (gradient: PhMe to PhMe/MeOH/Et3N, 8:1:1) to give 4... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cnc2cscc2n1 | c1cnc2cscc2n1.C1C[NH]CCN1 | c1cnc2cscc2n1.C1C[NH]CCN1 | HCl | CCO | null | null | C1CNCCN1.Clc1nc2cscc2nc1Cl>CCO>Clc1nc2cscc2nc1N1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b787b15b080f47e3b382789696040756 | Brc1cncnc1.OCCO>>OCCOc1cncnc1 | O([K])C(C)(C)C.C(CO)O.BrC=1C=NC=NC1>>N1=CN=CC(=C1)OCCO | Br[c:5]1[cH:6][n:7][cH:8][n:9][cH:10]1.[OH:1][CH2:2][CH2:3][OH:4]>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][n:7][cH:8][n:9][cH:10]1 | Brc1cncnc1.OCCO | OCCOc1cncnc1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | a445000eb5ed501274d93689ad5b9d45095af02deca02b6b541c8a834890a276 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1cncnc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1 | 6 | [{"value": 6.0, "product": "N1=CN=CC(=C1)OCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.0, "product": "N1=CN=CC(=C1)OCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | KO-t-Bu (7.70 g, 68.6 mmol) was added to ethylene glycol (10.45 g, 168.4 mmol) under stirring. The mixture was gently heated in order to consume all KO-t-Bu. 5-Bromopyrimidine (8.45 g, 53.1 mmol) was added to the light brownish mixture. After 8 h of stirring at 130° C., CH2Cl2 (50 mL) was added to the brownish reaction... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cncnc1 | c1cncnc1 | c1cncnc1 | HBr | C(Cl)Cl | null | null | Brc1cncnc1.OCCO>C(Cl)Cl>OCCOc1cncnc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ea419a2d02d941aeb1f9de96a3ac83be | Clc1nc2ccccc2nc1N1CCNCC1.OCCOc1cncnc1>>c1ccc2nc(N3CCNCC3)c(OCCOc3cncnc3)nc2c1 | ClC1=NC2=CC=CC=C2N=C1N1CCNCC1.N1=CN=CC(=C1)OCCO>>N1=CN=CC(=C1)OCCOC1=NC2=CC=CC=C2N=C1N1CCNCC1 | Cl[c:13]1[c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[n:5][c:4]2[cH:3][cH:2][cH:1][cH:26][c:25]2[n:24]1.[OH:14][CH2:15][CH2:16][O:17][c:18]1[cH:19][n:20][cH:21][n:22][cH:23]1>>[cH:1]1[cH:2][cH:3][c:4]2[n:5][c:6]([N:7]3[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]3)[c:13]([O:14][CH2:15][CH2:16][O:17][c:18]3[cH:19][n:20][... | Clc1nc2ccccc2nc1N1CCNCC1.OCCOc1cncnc1 | c1ccc2nc(N3CCNCC3)c(OCCOc3cncnc3)nc2c1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 76f684f6591b23c199df9d989c265ce73ff618d868cc26b6ec9cabfd7980b054 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc2nc(N3CCNCC3)c(OCCOc3cncnc3)nc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#7:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[#7:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:10]-[C:9]-[C:8] | null | [] | null | null | null | null | The title compound was prepared according to the procedure described in Example 162, Step 2, starting from 2-chloro-3-(1-piperazinyl)quinoxaline (0.66 g, 2.65 mmol; from is Example 162, Step 1) and 2-(5-pyrimidinyloxy)ethanol (0.45 g, 3.20 mmol). Yield 0.55 g (59%); mp 115-117° C.; HRMS m/z calcd for C18H20N6O2 (M)+352... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | c1ccc2nccnc2c1.C1C[NH]CCN1.c1cncnc1 | HCl | null | null | null | Clc1nc2ccccc2nc1N1CCNCC1.OCCOc1cncnc1>>c1ccc2nc(N3CCNCC3)c(OCCOc3cncnc3)nc2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-111ec1813902481295d106ac16594a7a | Clc1nc2ccccc2nc1N1CCNCC1.OCC1CCc2ccccc2O1>>c1ccc2c(c1)CCC(COc1nc3ccccc3nc1N1CCNCC1)O2 | ClC1=NC2=CC=CC=C2N=C1N1CCNCC1.O1C(CCC2=CC=CC=C12)CO>>O1C(CCC2=CC=CC=C12)COC1=NC2=CC=CC=C2N=C1N1CCNCC1 | Cl[c:12]1[n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[n:20][c:21]1[N:22]1[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]1.[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH:9]([CH2:10][OH:11])[O:28]2>>[cH:1]1[cH:2][cH:3][c:4]2[c:5]([cH:6]1)[CH2:7][CH2:8][CH:9]([CH2:10][O:11][c:12]1[n:13][c:14]3[cH:15][cH:16][cH:17][c... | Clc1nc2ccccc2nc1N1CCNCC1.OCC1CCc2ccccc2O1 | c1ccc2c(c1)CCC(COc1nc3ccccc3nc1N1CCNCC1)O2 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 76f684f6591b23c199df9d989c265ce73ff618d868cc26b6ec9cabfd7980b054 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc2c(c1)CCC(COc1nc3ccccc3nc1N1CCNCC1)O2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#7:7].[#8:8]-[C:9]-[C:10]-[OH;D1;+0:11]>>[#7:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:11]-[C:10]-[C:9]-[#8:8] | 23 | [{"value": 23.0, "product": "O1C(CCC2=CC=CC=C12)COC1=NC2=CC=CC=C2N=C1N1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title product was prepared according to the procedure described in Example 162, Step 2, starting from 2-chloro-3-(1-piperazinyl)quinoxaline (described in Example 162. Step 1) and 3,4-dihydro-2H-chromen-2-ylmethanol.* The product was obtained as a yellow amorphous substance: yield 23%; mp 202-204° C.; HRMS m/z calcd... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccc2nccnc2c1 | c1ccc2nccnc2c1 | c1ccc2c(c1)CCCO2.c1ccc2nccnc2c1.C1C[NH]CCN1 | HCl | null | null | null | Clc1nc2ccccc2nc1N1CCNCC1.OCC1CCc2ccccc2O1>>c1ccc2c(c1)CCC(COc1nc3ccccc3nc1N1CCNCC1)O2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b9144b3461b44c5883f04a23e98b4c56 | CN1CCNCC1.Clc1nccnc1Cl>>CN1CCN(c2nccnc2Cl)CC1 | ClC1=NC=CN=C1Cl.CN1CCNCC1>>ClC=1C(=NC=CN1)N1CCN(CC1)C | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:13][CH2:14]1.Cl[c:6]1[n:7][cH:8][cH:9][n:10][c:11]1[Cl:12]>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][cH:9][n:10][c:11]2[Cl:12])[CH2:13][CH2:14]1 | CN1CCNCC1.Clc1nccnc1Cl | CN1CCN(c2nccnc2Cl)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 343e2e4205e268ef018e3d4960cb45b93370e1763fb33dc0e04e91f5357b5af3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cnc(N2CCNCC2)cn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[Cl;D1;H0:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | 75 | [{"value": 75.0, "product": "ClC=1C(=NC=CN1)N1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.0, "product": "ClC=1C(=NC=CN1)N1CCN(CC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 60 | HOUR | A mixture of 2,3-dichloropyrazine (10.1 g, 68 mmol) and N-methylpiperazine (10.15 g, 100 mmol) in acetonitrile (250 mL) was stirred at room temperature for 60 h. The solvent was removed under reduced pressure and the residue was taken up in CHCl3/brine. The dried (MgSO4) organic layer was concentrated and the remaining... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1 | HCl | C(C)#N | null | 60 | CN1CCNCC1.Clc1nccnc1Cl>C(C)#N>CN1CCN(c2nccnc2Cl)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6518bc6102d44ed2a4b1deaa03cf31ac | CN1CCN(c2nccnc2Cl)CC1.OCC1COc2ccccc2O1>>CN1CCN(c2nccnc2OCC2COc3ccccc3O2)CC1.Cl | ClC=1C(=NC=CN1)N1CCN(CC1)C.OCC1COC2=C(O1)C=CC=C2.Cl>>Cl.Cl.CN1CCN(CC1)C=1C(=NC=CN1)OCC1COC2=C(O1)C=CC=C2 | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][cH:9][n:10][c:11]2[Cl:26])[CH2:24][CH2:25]1.[OH:12][CH2:13][CH:14]1[CH2:15][O:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[O:23]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][cH:9][n:10][c:11]2[O:12][CH2:13][CH:14]2[CH2:15][O:16][c:17]3[cH:18][cH:19][cH:20][cH:... | CN1CCN(c2nccnc2Cl)CC1.OCC1COc2ccccc2O1 | CN1CCN(c2nccnc2OCC2COc3ccccc3O2)CC1.Cl | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8088ac3623a2ee47f375f73ca665bec9cf80b1384463e6e2f03125aecbcea517 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc2c(c1)OCC(COc1nccnc1N1CCNCC1)O2 | [#7:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:[c;H0;D3;+0:7]:1-[Cl;H0;D1;+0:8].[#8:9]-[C:10]-[C:11]-[OH;D1;+0:12]>>[#7:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[#7;a:6]:[c;H0;D3;+0:7]:1-[O;H0;D2;+0:12]-[C:11]-[C:10]-[#8:9].[ClH;D0;+0:8] | 87 | [{"value": 87.0, "product": "Cl.Cl.CN1CCN(CC1)C=1C(=NC=CN1)OCC1COC2=C(O1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared according to the procedure described in Example 90, Step 2, starting from 1-(3-chloro-2-pyrazinyl)-4-methylpiperazine (described in Example 169, Step 1) and 2-hydroxymethyl-2,3-dihydro-1,4-benzodioxine. Yield 87%; mp 160-167° C. Anal. (C18H22N4O3.2 HCl) H, N; C: calcd, 52.06; found, 52.6... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cnccn1 | c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1.c1ccc2c(c1)OCCO2 | null | null | null | null | CN1CCN(c2nccnc2Cl)CC1.OCC1COc2ccccc2O1>>CN1CCN(c2nccnc2OCC2COc3ccccc3O2)CC1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-af344c9d341d4a51a1ab9241831ef034 | CC1CN(Cc2ccccc2)CCN1.Clc1nccnc1Cl>>CC1CN(Cc2ccccc2)CCN1c1nccnc1Cl | ClC1=NC=CN=C1Cl.C(C1=CC=CC=C1)N1CC(NCC1)C.C(=O)([O-])[O-].[K+].[K+]>>ClC=1C(=NC=CN1)N1C(CN(CC1)CC1=CC=CC=C1)C | [CH3:1][CH:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13][NH:14]1.Cl[c:15]1[n:16][cH:17][cH:18][n:19][c:20]1[Cl:21]>>[CH3:1][CH:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][CH2:13][N:14]1[c:15]1[n:16][cH:17][cH:18][n:19][c:20]1[Cl:21] | CC1CN(Cc2ccccc2)CCN1.Clc1nccnc1Cl | CC1CN(Cc2ccccc2)CCN1c1nccnc1Cl | null | null | C(C)#N.CCOCC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a752b8271b175119ca80c4ec7eb95ecc759b3641e02647044be70538f5c2e04a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CN2CCN(c3cnccn3)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[C;D1;H3:8]-[C:9]1-[C:10]-[#7:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[C;D1;H3:8]-[C:9]1-[C:10]-[#7:11]-[C:12]-[C:13]-[N;H0;D3;+0:14]-1-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7] | 28 | [{"value": 28.0, "product": "ClC=1C(=NC=CN1)N1C(CN(CC1)CC1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | 115 | CELSIUS | 17 | HOUR | A mixture of 2,3-dichloropyrazine (0.332 g, 2.23 mmol), 1-benzyl-3-methylpiperazine* (0.423 g, 2.23 mmol), and K2CO3 (0.339 g, 2.45 mmol) in acetonitrile (2.5 mL) was stirred at 115° C. for 17 h in a sealed tube. The reaction mixture was diluted with ether, filtered, and concentrated. The brownish oily residue was puri... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1 | C1C[NH]CC[NH]1.c1ccccc1.c1cnccn1 | HCl | C(C)#N.CCOCC | 115 | 17 | CC1CN(Cc2ccccc2)CCN1.Clc1nccnc1Cl>C(C)#N.CCOCC>CC1CN(Cc2ccccc2)CCN1c1nccnc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c9abdb61bf73430ea34069be68fd526a | C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1nccnc1Cl.OCCOc1cccnc1>>C[C@@H]1CNCCN1c1nccnc1OCCOc1cccnc1.Cl | N1=CC(=CC=C1)OCCO.ClC=1C(=NC=CN1)N1[C@@H](CN(CC1)C(=O)OC(C)(C)C)C>>Cl.C[C@H]1N(CCNC1)C1=NC=CN=C1OCCOC=1C=NC=CC1 | CC(C)(C)OC(=O)[N:4]1[CH2:3][C@@H:2]([CH3:1])[N:7]([c:8]2[n:9][cH:10][cH:11][n:12][c:13]2[Cl:24])[CH2:6][CH2:5]1.[OH:14][CH2:15][CH2:16][O:17][c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1>>[CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[c:8]1[n:9][cH:10][cH:11][n:12][c:13]1[O:14][CH2:15][CH2:16][O:17][c:18]1[cH:19][cH:20... | C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1nccnc1Cl.OCCOc1cccnc1 | C[C@@H]1CNCCN1c1nccnc1OCCOc1cccnc1.Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 998ffad1775db60ae157815d41333cea1a7927f6da96bda38daf98637859550f | 3e7ed0fa3e4b6ea635cf6ae632f3bebf09edf2c710a17e18ef492c2cf7680a0d | c1cncc(OCCOc2nccnc2N2CCNCC2)c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4](-[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c;H0;D3;+0:10]:2-[Cl;H0;D1;+0:11])-[C:12]-[C:13]-1.[C:14]-[C:15]-[OH;D1;+0:16]>>[C:14]-[C:15]-[O;H0;D2;+0:16]-[c;H0;D3;+0:10]1:[#7;a:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1-[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:13]-[C:12]-1.[ClH;D0;+0:1... | null | [] | null | null | null | null | The title compound was prepared starting from 2-(3-pyridyloxy)ethanol (from Example 150, Step 1) and 3-chloro-2-[4-tert-butoxycarbonyl-(2R)-methyl-1-piperazinyl]pyrazine (from Example 172, Step 2). The pure free base was precipitated as its hydrochloride salt with HCl/ether to give the title compound as white crystals:... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Primary alcohol.Boc | Ether.Secondary amine | C1C[NH]CC[NH]1.c1cnccn1 | C1C[NH]CCN1.c1cnccn1 | C1C[NH]CCN1.c1cnccn1.c1ccncc1 | HO- | null | null | null | C[C@@H]1CN(C(=O)OC(C)(C)C)CCN1c1nccnc1Cl.OCCOc1cccnc1>>C[C@@H]1CNCCN1c1nccnc1OCCOc1cccnc1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-59404f350ba142e29024c404daba0295 | C[C@H]1CN(C(=O)OC(C)(C)C)CCN1c1nccnc1Cl.OCCOc1cccnc1>>C[C@H]1CNCCN1c1nccnc1OCCOc1cccnc1.Cl | N1=CC(=CC=C1)OCCO.ClC=1C(=NC=CN1)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C>>Cl.C[C@@H]1N(CCNC1)C1=NC=CN=C1OCCOC=1C=NC=CC1 | CC(C)(C)OC(=O)[N:4]1[CH2:3][C@H:2]([CH3:1])[N:7]([c:8]2[n:9][cH:10][cH:11][n:12][c:13]2[Cl:24])[CH2:6][CH2:5]1.[OH:14][CH2:15][CH2:16][O:17][c:18]1[cH:19][cH:20][cH:21][n:22][cH:23]1>>[CH3:1][C@H:2]1[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[c:8]1[n:9][cH:10][cH:11][n:12][c:13]1[O:14][CH2:15][CH2:16][O:17][c:18]1[cH:19][cH:20][... | C[C@H]1CN(C(=O)OC(C)(C)C)CCN1c1nccnc1Cl.OCCOc1cccnc1 | C[C@H]1CNCCN1c1nccnc1OCCOc1cccnc1.Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 998ffad1775db60ae157815d41333cea1a7927f6da96bda38daf98637859550f | 3e7ed0fa3e4b6ea635cf6ae632f3bebf09edf2c710a17e18ef492c2cf7680a0d | c1cncc(OCCOc2nccnc2N2CCNCC2)c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4](-[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c;H0;D3;+0:10]:2-[Cl;H0;D1;+0:11])-[C:12]-[C:13]-1.[C:14]-[C:15]-[OH;D1;+0:16]>>[C:14]-[C:15]-[O;H0;D2;+0:16]-[c;H0;D3;+0:10]1:[#7;a:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1-[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:13]-[C:12]-1.[ClH;D0;+0:1... | 58 | [{"value": 58.0, "product": "Cl.C[C@@H]1N(CCNC1)C1=NC=CN=C1OCCOC=1C=NC=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared starting from 2-(3-pyridyloxy)ethanol (from Example 150, Step 1) and 3-chloro-2-[4-tert-butoxycarbonyl-(2S)-methyl-1-piperazinyl]pyrazine (prepared according to the procedure of Example 172, Step 2, with the exception that (2S)-methyl piperazine was substituted for (2R)-methylpiperazine)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Primary alcohol.Boc | Ether.Secondary amine | C1C[NH]CC[NH]1.c1cnccn1 | C1C[NH]CCN1.c1cnccn1 | C1C[NH]CCN1.c1cnccn1.c1ccncc1 | HO- | null | null | null | C[C@H]1CN(C(=O)OC(C)(C)C)CCN1c1nccnc1Cl.OCCOc1cccnc1>>C[C@H]1CNCCN1c1nccnc1OCCOc1cccnc1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d352de1f45e24d788e221a54fd976db0 | C[C@H]1CN(C(=O)OC(C)(C)C)CCN1c1nccnc1Cl.OCCOc1ccccc1>>C[C@H]1CNCCN1c1nccnc1OCCOc1ccccc1.Cl | O(C1=CC=CC=C1)CCO.ClC=1C(=NC=CN1)N1[C@H](CN(CC1)C(=O)OC(C)(C)C)C>>Cl.C[C@@H]1N(CCNC1)C1=NC=CN=C1OCCOC1=CC=CC=C1 | CC(C)(C)OC(=O)[N:4]1[CH2:3][C@H:2]([CH3:1])[N:7]([c:8]2[n:9][cH:10][cH:11][n:12][c:13]2[Cl:24])[CH2:6][CH2:5]1.[OH:14][CH2:15][CH2:16][O:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][C@H:2]1[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[c:8]1[n:9][cH:10][cH:11][n:12][c:13]1[O:14][CH2:15][CH2:16][O:17][c:18]1[cH:19][cH:20]... | C[C@H]1CN(C(=O)OC(C)(C)C)CCN1c1nccnc1Cl.OCCOc1ccccc1 | C[C@H]1CNCCN1c1nccnc1OCCOc1ccccc1.Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 998ffad1775db60ae157815d41333cea1a7927f6da96bda38daf98637859550f | 3e7ed0fa3e4b6ea635cf6ae632f3bebf09edf2c710a17e18ef492c2cf7680a0d | c1ccc(OCCOc2nccnc2N2CCNCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4](-[c:5]2:[#7;a:6]:[c:7]:[c:8]:[#7;a:9]:[c;H0;D3;+0:10]:2-[Cl;H0;D1;+0:11])-[C:12]-[C:13]-1.[C:14]-[C:15]-[OH;D1;+0:16]>>[C:14]-[C:15]-[O;H0;D2;+0:16]-[c;H0;D3;+0:10]1:[#7;a:9]:[c:8]:[c:7]:[#7;a:6]:[c:5]:1-[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:13]-[C:12]-1.[ClH;D0;+0:1... | 68 | [{"value": 68.0, "product": "Cl.C[C@@H]1N(CCNC1)C1=NC=CN=C1OCCOC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared starting from 2-phenoxy-1-ethanol and 3-chloro-2-[4-tert-butoxycarbonyl-(2S)-methyl-1-piperazinyl]pyrazine (prepared according to the procedure of Example 172, Step 2, with the exception that (2S)-methylpiperazine was to substituted for (2R)-methylpiperazine). MS m/z 315 (M+H)+. Yield 68... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Primary alcohol.Boc | Ether.Secondary amine | C1C[NH]CC[NH]1.c1cnccn1 | C1C[NH]CCN1.c1cnccn1 | C1C[NH]CCN1.c1cnccn1.c1ccccc1 | HO- | null | null | null | C[C@H]1CN(C(=O)OC(C)(C)C)CCN1c1nccnc1Cl.OCCOc1ccccc1>>C[C@H]1CNCCN1c1nccnc1OCCOc1ccccc1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-857a2678dc564e43936085345f896338 | Nc1ccc2cccc(O)c2n1.O=C1OCCO1>>Nc1ccc2cccc(OCCO)c2n1 | NC1=NC2=C(C=CC=C2C=C1)O.C1(OCCO1)=O.O([K])C(C)(C)C>>NC1=NC2=C(C=CC=C2C=C1)OCCO | [NH2:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([OH:10])[c:14]2[n:15]1.O=C1O[CH2:11][CH2:12][O:13]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][OH:13])[c:14]2[n:15]1 | Nc1ccc2cccc(O)c2n1.O=C1OCCO1 | Nc1ccc2cccc(OCCO)c2n1 | null | null | [Cl-].[Na+].O.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 34950df4dc1bc6c778d9cfa26c728e443e4886f7382a4283f1fbae4a959b8c37 | c6f5c5ba2d936b513bc18d6bcb095f40591aa3ba8700a9f5b8ecbbdd690dab72 | c1ccc2ncccc2c1 | O=C1-O-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1.[OH;D1;+0:4]-[c:5](:[c:6]):[c:7](:[c:8]):[#7;a:9]:[c:10]>>[OH;D1;+0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7](:[c:8]):[#7;a:9]:[c:10] | 28 | [{"value": 28.0, "product": "NC1=NC2=C(C=CC=C2C=C1)OCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.7, "product": "NC1=NC2=C(C=CC=C2C=C1)OCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 15 | HOUR | A mixture of 2-amino-8-quinolinol (3.20 g, 20.0 mmol), ethylene carbonate (1.76 g, 20.0 mmol) and KO-t-Bu (2.24 g, 20.0 mmol) in DMF (20 mL) was stirred at 90° C. for 15 h. The mixture was poured into brine, extracted with EtOAc, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by chroma... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Aromatic alcohol | Ether.Primary alcohol | C1COCO1 | null | c1ccc2ncccc2c1 | Other | [Cl-].[Na+].O.CN(C)C=O | 90 | 15 | Nc1ccc2cccc(O)c2n1.O=C1OCCO1>[Cl-].[Na+].O.CN(C)C=O>Nc1ccc2cccc(OCCO)c2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-281c91867e344a1896f5d9a576cd628a | BrCc1ccccc1.CCC1CNCCN1>>CCC1CN(Cc2ccccc2)CCN1 | C(C1=CC=CC=C1)Br.C(C)C1NCCNC1>>C(C1=CC=CC=C1)N1CC(NCC1)CC | Br[CH2:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[CH3:1][CH2:2][CH:3]1[CH2:4][NH:5][CH2:13][CH2:14][NH:15]1>>[CH3:1][CH2:2][CH:3]1[CH2:4][N:5]([CH2:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][NH:15]1 | BrCc1ccccc1.CCC1CNCCN1 | CCC1CN(Cc2ccccc2)CCN1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f302e0798768754bbc60184db743cc667f2eb421e32357dcb3b8d027a535a203 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1):[c:4] | 70.3 | [{"value": 70.0, "product": "C(C1=CC=CC=C1)N1CC(NCC1)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.3, "product": "C(C1=CC=CC=C1)N1CC(NCC1)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Benzyl bromide (38.7 g, 0.22 mol) was added in portions to an ice cold (˜0° C.) solution of 2-ethylpiperazine (25 g, 0.22 mol) in DMF (150 mL) with such a rate that the temperature did not exceed 20° C. The mixture was stirred for 1 h, the solvent was evaporated and the residue was partitioned between CHCl3/0.5 M HCl. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCCN1 | C1CNCC[NH]1 | C1CNCC[NH]1.c1ccccc1 | HBr | CN(C)C=O | null | 1 | BrCc1ccccc1.CCC1CNCCN1>CN(C)C=O>CCC1CN(Cc2ccccc2)CCN1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8d823ab1607241569e220e5396059354 | CC(Cl)OC(=O)Cl.CCC1CN(Cc2ccccc2)CCN1c1nccnc1Cl>>CCC1CNCCN1c1nccnc1Cl.Cl | ClC(=O)OC(C)Cl.C(C1=CC=CC=C1)N1CC(N(CC1)C1=NC=CN=C1Cl)CC>>Cl.ClC=1C(=NC=CN1)N1C(CNCC1)CC | CC(Cl)OC(=O)[Cl:16].c1ccc(C[N:5]2[CH2:4][CH:3]([CH2:2][CH3:1])[N:8]([c:9]3[n:10][cH:11][cH:12][n:13][c:14]3[Cl:15])[CH2:7][CH2:6]2)cc1>>[CH3:1][CH2:2][CH:3]1[CH2:4][NH:5][CH2:6][CH2:7][N:8]1[c:9]1[n:10][cH:11][cH:12][n:13][c:14]1[Cl:15].[ClH:16] | CC(Cl)OC(=O)Cl.CCC1CN(Cc2ccccc2)CCN1c1nccnc1Cl | CCC1CNCCN1c1nccnc1Cl.Cl | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 0559448e597bb3e9f7586f3b87f9ebfb55c3345c334385974272c6d5f0ce7048 | 8680972761abf0bd12e62e23250487041204d99e9f76a29275e470fb95a71c86 | c1cnc(N2CCNCC2)cn1 | C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1)-c1:c:c:c:c:c:1.C-C(-Cl)-O-C(=O)-[Cl;H0;D1;+0:7]>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1.[ClH;D0;+0:7] | null | [] | null | null | 48 | HOUR | 1-Chloroethyl chloroformate (2.11 g, 15.2 mmol) was added with a syringe during 1 h to an ice cold (˜0° C.) solution of 4-benzyl-1-(3-chloro-2-pyrazinyl)-2-ethylpiperazine (3.22 g, 10.1 mmol, from Step 2) in dry CH2Cl2 (30 mL). The reaction-was-allowed to slowly reach room temperature and stirred for 48 h. The solvent ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary halide.Ether.Tertiary amine | Secondary amine | c1ccccc1.C1C[NH]CC[NH]1 | C1C[NH]CCN1 | C1C[NH]CCN1.c1cnccn1 | HCl | C(Cl)Cl | null | 48 | CC(Cl)OC(=O)Cl.CCC1CN(Cc2ccccc2)CCN1c1nccnc1Cl>C(Cl)Cl>CCC1CNCCN1c1nccnc1Cl.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a0941e14d1cf49c7af52b4affb248993 | BrCc1ccccc1.C[C@@H]1CNC[C@H](C)N1>>C[C@@H]1CN(Cc2ccccc2)C[C@H](C)N1 | C[C@@H]1N[C@@H](CNC1)C.C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)N1C[C@H](N[C@H](C1)C)C | Br[CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:12][C@H:13]([CH3:14])[NH:15]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][C@H:13]([CH3:14])[NH:15]1 | BrCc1ccccc1.C[C@@H]1CNC[C@H](C)N1 | C[C@@H]1CN(Cc2ccccc2)C[C@H](C)N1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | f302e0798768754bbc60184db743cc667f2eb421e32357dcb3b8d027a535a203 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#7:5]-[C:10]-[C:9]-1):[c:4] | 68.5 | [{"value": 68.0, "product": "C(C1=CC=CC=C1)N1C[C@H](N[C@H](C1)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.5, "product": "C(C1=CC=CC=C1)N1C[C@H](N[C@H](C1)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | To an ice cold (˜0° C.) suspension of cis-2,6-dimethylpiperazine (4.0 g, 35 mmol) in DMF (100 mL) was benzyl bromide (6.0 g, 35.0 mmol) added in portions under a period of 45 min and the reaction mixture was stirred at room temperature for 48 h. The solvent was evaporated from the suspension and the residue was dissolv... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCCN1 | C1CNCC[NH]1 | C1CNCC[NH]1.c1ccccc1 | HBr | CN(C)C=O | null | 48 | BrCc1ccccc1.C[C@@H]1CNC[C@H](C)N1>CN(C)C=O>C[C@@H]1CN(Cc2ccccc2)C[C@H](C)N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1d096fb340f442a6b7efa31fc2fc38c8 | C[C@@H]1CN(Cc2ccccc2)C[C@H](C)N1.Clc1nccnc1Cl>>C[C@@H]1CN(Cc2ccccc2)C[C@H](C)N1c1nccnc1Cl | ClC1=NC=CN=C1Cl.C(C1=CC=CC=C1)N1C[C@H](N[C@H](C1)C)C.C(CCC)N(CCCC)CCCC.C1(=CC=CC=C1)OC1=CC=CC=C1>>C(C1=CC=CC=C1)N1C[C@@H](N([C@@H](C1)C)C1=NC=CN=C1Cl)C | [CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][C@H:13]([CH3:14])[NH:15]1.Cl[c:16]1[n:17][cH:18][cH:19][n:20][c:21]1[Cl:22]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[CH2:12][C@H:13]([CH3:14])[N:15]1[c:16]1[n:17][cH:18][cH:19][n:20][c:21]1[Cl:22] | C[C@@H]1CN(Cc2ccccc2)C[C@H](C)N1.Clc1nccnc1Cl | C[C@@H]1CN(Cc2ccccc2)C[C@H](C)N1c1nccnc1Cl | null | null | C1(=CC=CC=C1)C.CCOC(=O)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | a752b8271b175119ca80c4ec7eb95ecc759b3641e02647044be70538f5c2e04a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CN2CCN(c3cnccn3)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[C;D1;H3:8]-[C:9]1-[C:10]-[#7:11]-[C:12]-[C:13](-[C;D1;H3:14])-[NH;D2;+0:15]-1>>[C;D1;H3:8]-[C:9]1-[C:10]-[#7:11]-[C:12]-[C:13](-[C;D1;H3:14])-[N;H0;D3;+0:15]-1-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7] | null | [] | 220 | CELSIUS | null | null | A mixture of 2,3-dichloropyrazine (4.9 g, 32.9 mmol), 1-benzyl-cis-3,5-dimethylpiperazine (5.9 g, 29.0 mmol), tributylamine (5.9 g, 32 mmol) and diphenyl ether (70 mL) was heated in a sealed tube at 220° C. for 3 days. The reaction mixture was cooled to ambient temperature and EtOAc (200 mL) and toluene (100 mL) were a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1 | C1C[NH]CC[NH]1.c1ccccc1.c1cnccn1 | HCl | C1(=CC=CC=C1)C.CCOC(=O)C | 220 | null | C[C@@H]1CN(Cc2ccccc2)C[C@H](C)N1.Clc1nccnc1Cl>C1(=CC=CC=C1)C.CCOC(=O)C>C[C@@H]1CN(Cc2ccccc2)C[C@H](C)N1c1nccnc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-21bc5e2924824050abb3a8a5e423700e | CC(=O)Nc1ccc2cccc(OCCOc3nccnc3N3CCN(C(=O)OC(C)(C)C)CC3)c2n1>>CC(=O)Nc1ccc2cccc(OCCOc3nccnc3N3CCNCC3)c2n1 | C(=O)(C(F)(F)F)O.C(C)(=O)NC1=NC2=C(C=CC=C2C=C1)OCCOC=1C(=NC=CN1)N1CCN(CC1)C(=O)OC(C)(C)C>>N1(CCNCC1)C=1C(=NC=CN1)OCCOC=1C=CC=C2C=CC(=NC12)NC(C)=O | CC(C)(C)OC(=O)[N:26]1[CH2:25][CH2:24][N:23]([c:22]2[c:17]([O:16][CH2:15][CH2:14][O:13][c:12]3[cH:11][cH:10][cH:9][c:8]4[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[n:30][c:29]43)[n:18][cH:19][cH:20][n:21]2)[CH2:28][CH2:27]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([O:13][CH2:14][CH... | CC(=O)Nc1ccc2cccc(OCCOc3nccnc3N3CCN(C(=O)OC(C)(C)C)CC3)c2n1 | CC(=O)Nc1ccc2cccc(OCCOc3nccnc3N3CCNCC3)c2n1 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cnc2c(OCCOc3nccnc3N3CCNCC3)cccc2c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | null | null | 1 | HOUR | TFA (1.5 mL) was added to a solution of the product from Step 2 (112 mg, 0.22 mmol) in CH2Cl2(1.5 mL) at 0° C. and the mixture was stirred under inert atmosphere for 1 h. The reaction mixture was diluted with CH2Cl2 and washed with 2 M aqueous NaOH (×4) and brine. The organic layer was dried (MgSO4) and concentrated. T... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccc2ncccc2c1.c1cnccn1.C1C[NH]CCN1 | HO- | C(Cl)Cl | null | 1 | CC(=O)Nc1ccc2cccc(OCCOc3nccnc3N3CCN(C(=O)OC(C)(C)C)CC3)c2n1>C(Cl)Cl>CC(=O)Nc1ccc2cccc(OCCOc3nccnc3N3CCNCC3)c2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9135519da0ae430e866d80699a0c2807 | CN.Oc1cccc2ccc(Cl)nc12>>CNc1ccc2cccc(O)c2n1 | ClC1=NC2=C(C=CC=C2C=C1)O.NC>>CNC1=NC2=C(C=CC=C2C=C1)O | [CH3:1][NH2:2].Cl[c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([OH:11])[c:12]2[n:13]1>>[CH3:1][NH:2][c:3]1[cH:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([OH:11])[c:12]2[n:13]1 | CN.Oc1cccc2ccc(Cl)nc12 | CNc1ccc2cccc(O)c2n1 | null | null | CCO | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 45e8470a78418ade39424f40732aa5ecf6717a7e5d47830a67429c5970ebd551 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2ncccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[NH2;D1;+0:7]>>[C;D1;H3:6]-[NH;D2;+0:7]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | 100 | CELSIUS | null | null | To a solution of 2-chloro-8-hydroxyquinoline*(2.0 g, 11.1 mmol) in EtOH (40 mL) was added H2NMe (40% aqueous solution, 40 mL, 464 mmol). The mixture was heated in a sealed Pyrex tube at 100° C. for 24 h. The solvent was evaporated and the resulting crude product was purified by column chromatography [gradient: CH2Cl2/M... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | HCl | CCO | 100 | null | CN.Oc1cccc2ccc(Cl)nc12>CCO>CNc1ccc2cccc(O)c2n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b2721133025143bf80ef7c56ebf831f0 | O=C1OCCO1.Oc1cccc2c1OCO2>>OCCOc1cccc2c1OCO2 | C(=O)=O.O1COC2=C1C=CC=C2O.C1(OCCO1)=O.C(=O)([O-])[O-].[K+].[K+]>>O1COC2=C1C=CC=C2OCCO | O=C1O[CH2:3][CH2:2][O:1]1.[OH:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[O:11][CH2:12][O:13]2>>[OH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9]2[c:10]1[O:11][CH2:12][O:13]2 | O=C1OCCO1.Oc1cccc2c1OCO2 | OCCOc1cccc2c1OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 34950df4dc1bc6c778d9cfa26c728e443e4886f7382a4283f1fbae4a959b8c37 | c6f5c5ba2d936b513bc18d6bcb095f40591aa3ba8700a9f5b8ecbbdd690dab72 | c1ccc2c(c1)OCO2 | O=C1-O-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1.[#8:4]-[c:5]:[c:6](-[OH;D1;+0:7]):[c:8]>>[#8:4]-[c:5]:[c:6](-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3]):[c:8] | 65 | [{"value": 65.0, "product": "O1COC2=C1C=CC=C2OCCO", "details": "PERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | A mixture of 1,3-benzodioxol-4-ol*(0.74 g, 5.36 mmol), ethylene carbonate (0.47 g, 5.3 mmol) and K2CO3 (0.67 g, 4.8 mmol) in DMF (30 mL) was heated at 150° C. After the evolution of carbon dioxide had ceased (1 h), the reaction mixture was filtered and concentrated. The crude product was purified by chromatography on s... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester.Aromatic alcohol | Ether.Primary alcohol | C1COCO1 | null | c1ccc2c(c1)OCO2 | Other | CN(C)C=O | 150 | null | O=C1OCCO1.Oc1cccc2c1OCO2>CN(C)C=O>OCCOc1cccc2c1OCO2 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ea7442f0cb4e480d9edccf434b38b7b6 | C1CNCCN1.Cc1nc(Cl)c(Cl)nc1C>>Cc1nc(Cl)c(N2CCNCC2)nc1C | ClC1=NC(=C(N=C1Cl)C)C.N1CCNCC1>>ClC1=NC(=C(N=C1N1CCNCC1)C)C | [NH:7]1[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]1.Cl[c:6]1[c:4]([Cl:5])[n:3][c:2]([CH3:1])[c:14]([CH3:15])[n:13]1>>[CH3:1][c:2]1[n:3][c:4]([Cl:5])[c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[n:13][c:14]1[CH3:15] | C1CNCCN1.Cc1nc(Cl)c(Cl)nc1C | Cc1nc(Cl)c(N2CCNCC2)nc1C | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 76b5a96b5c73afc00c162a6d1bfbc74a19ffca41d4e87b05da47a491d82e0c1f | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cnc(N2CCNCC2)cn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[Cl;D1;H0:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | The title compound was prepared according, to the procedure described in Example 90. Step 1, starting from 2,3-dichloro-5,6-dimethylpyrazine*(0.60 g, 3.39 mmol) and piperazine (0.88 g, 10.2 mmol). Yield 0.51 g (66%). MS m/z 226 (M)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cnccn1 | c1cnccn1.C1C[NH]CCN1 | c1cnccn1.C1C[NH]CCN1 | HCl | null | null | null | C1CNCCN1.Cc1nc(Cl)c(Cl)nc1C>>Cc1nc(Cl)c(N2CCNCC2)nc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-12c949c752284d15a4d152db57de8ac2 | BrCCOc1ccccc1.CC(C)(C)OC(=O)N1CCN(c2ccccc2O)CC1>>c1ccc(OCCOc2ccccc2N2CCNCC2)cc1 | Cl.OC1=C(C=CC=C1)N1CCN(CC1)C(=O)OC(C)(C)C.O([Na])C(C)(C)C.BrCCOC1=CC=CC=C1>>Cl.O(C1=CC=CC=C1)CCOC1=C(C=CC=C1)N1CCNCC1 | Br[CH2:8][CH2:7][O:6][c:5]1[cH:4][cH:3][cH:2][cH:23][cH:22]1.CC(C)(C)OC(=O)[N:19]1[CH2:18][CH2:17][N:16]([c:15]2[c:10]([OH:9])[cH:11][cH:12][cH:13][cH:14]2)[CH2:21][CH2:20]1>>[cH:2]1[cH:3][cH:4][c:5]([O:6][CH2:7][CH2:8][O:9][c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[N:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]2)[cH:22... | BrCCOc1ccccc1.CC(C)(C)OC(=O)N1CCN(c2ccccc2O)CC1 | c1ccc(OCCOc2ccccc2N2CCNCC2)cc1 | null | null | COCCOC | Heteroatom Alkylation and Arylation | OtherReaction | 444ecc2d0412cb1a950e9e9f29bd9c0abecf9eb0895dec2f68793ffa397484ac | ad231dde21a154e6081768f6095b5b5f8aaa932a69f458a3689bd80feb1694b9 | c1ccc(OCCOc2ccccc2N2CCNCC2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:4]1-[C:5]-[C:6]-[#7:7](-[c:8]:[c:9](-[OH;D1;+0:10]):[c:11])-[C:12]-[C:13]-1>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[c:9](:[c:11]):[c:8]-[#7:7]1-[C:6]-[C:5]-[NH;D2;+0:4]-[C:13]-[C:12]-1 | null | [] | 55 | CELSIUS | 5 | MINUTE | The product from Step 1 above (0.55 g, 2.0 mmol) was added to a stirred solution of NaO-t-Bu (0.55 g. 2.0 mmol) in DME (5 mL). After 5 min, β-bromophenetole (0.56 g, 2.8 mmol) was added, and the reaction was stirred at 55° C. for 15 h, 2 M HCl was added, and the reaction mixture was stirred for another 3 h. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carbamic ester.Ether.Aromatic alcohol.Boc | Ether.Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.c1ccccc1.C1C[NH]CCN1 | HBr | COCCOC | 55 | 0.083333 | BrCCOc1ccccc1.CC(C)(C)OC(=O)N1CCN(c2ccccc2O)CC1>COCCOC>c1ccc(OCCOc2ccccc2N2CCNCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e6a6e8092c0d457c95443cabef8cf56b | BrCCOc1ccccc1.Oc1cccnc1Cl>>Clc1ncccc1OCCOc1ccccc1 | ClC1=NC=CC=C1O.BrCCOC1=CC=CC=C1.C(=O)([O-])[O-].[K+].[K+]>>ClC1=NC=CC=C1OCCOC1=CC=CC=C1 | Br[CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1.[Cl:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[OH:8]>>[Cl:1][c:2]1[n:3][cH:4][cH:5][cH:6][c:7]1[O:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | BrCCOc1ccccc1.Oc1cccnc1Cl | Clc1ncccc1OCCOc1ccccc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(OCCOc2cccnc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[Cl;D1;H0:4]-[c:5](:[#7;a:6]:[c:7]):[c:8](-[OH;D1;+0:9]):[c:10]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:9]-[c:8](:[c:10]):[c:5](-[Cl;D1;H0:4]):[#7;a:6]:[c:7] | 74 | [{"value": 74.0, "product": "ClC1=NC=CC=C1OCCOC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.3, "product": "ClC1=NC=CC=C1OCCOC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of 2-chloro-3-hydroxypyridine (3.0 g, 23.1 mmol), β-bromophenetole (4.66 g, 23.2 mmol), and K2CO3 (8.0 g, 57.9 mmol) in DMF (50 mL) was heated at 100° C. for 1.5 h. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and H2O. The organic phase was dried (MgSO4), filter... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccncc1.c1ccccc1 | HBr | CN(C)C=O | 100 | null | BrCCOc1ccccc1.Oc1cccnc1Cl>CN(C)C=O>Clc1ncccc1OCCOc1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-28325c9c9feb493b8fdcc874c61df9d2 | C1CNCCN1.Clc1ncccc1OCCOc1ccccc1>>Cl.Cl.c1ccc(OCCOc2cccnc2N2CCNCC2)cc1 | ClC1=NC=CC=C1OCCOC1=CC=CC=C1.O.O.O.O.O.O.N1CCNCC1>>Cl.Cl.O(C1=CC=CC=C1)CCOC=1C(=NC=CC1)N1CCNCC1 | [NH:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1.[Cl:1][c:16]1[c:11]([O:10][CH2:9][CH2:8][O:7][c:6]2[cH:5][cH:4][cH:3][cH:24][cH:23]2)[cH:12][cH:13][cH:14][n:15]1>>[ClH:1].[ClH:2].[cH:3]1[cH:4][cH:5][c:6]([O:7][CH2:8][CH2:9][O:10][c:11]2[cH:12][cH:13][cH:14][n:15][c:16]2[N:17]2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]2)[... | C1CNCCN1.Clc1ncccc1OCCOc1ccccc1 | Cl.Cl.c1ccc(OCCOc2cccnc2N2CCNCC2)cc1 | null | null | O | Functional Group Addition | Ullmann-Goldberg Substitution amine | 921113aa3868ec5a931266cc4a65a0a885aa6f14ae137870ff36c75fbca6bedb | 61fffeaa75edcf21f8db97fe82a634291f4dc5c49705965cea81dd0b490dbebd | c1ccc(OCCOc2cccnc2N2CCNCC2)cc1 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[#8:7]-[c:8](:[c:9]):[c;H0;D3;+0:10](-[Cl;H0;D1;+0:11]):[#7;a:12]:[c:13]>>[#8:7]-[c:8](:[c:9]):[c;H0;D3;+0:10](-[N;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1):[#7;a:12]:[c:13].[ClH;D0;+0:11] | null | [] | 165 | CELSIUS | null | null | A mixture of the product from Step 1 above (0.84 g, 3.1 mmol) and piperazine hexahydrate (5.3 g, 27.3 mmol) was heated in a sealed tube at 165° C. for 1 h. After cooling, the mixture was diluted with water (100 mL) and extracted twice with EtOAc. The combined and dried (MgSO4) organic phases were concentrated in vacuo ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1ccncc1 | c1ccncc1.C1C[NH]CCN1 | c1ccccc1.c1ccncc1.C1C[NH]CCN1 | Other | O | 165 | null | C1CNCCN1.Clc1ncccc1OCCOc1ccccc1>O>Cl.Cl.c1ccc(OCCOc2cccnc2N2CCNCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1735d8f2fbc045309b6f3ada227af701 | Clc1nccnc1N1CCNCC1.O=C1CCC(=O)N1Cl>>Clc1cnc(N2CCNCC2)c(Cl)n1 | ClC1=NC=CN=C1N1CCNCC1.ClN1C(CCC1=O)=O>>ClC=1C(=NC=C(N1)Cl)N1CCNCC1 | [cH:2]1[cH:3][n:4][c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[c:12]([Cl:13])[n:14]1.O=C1CCC(=O)N1[Cl:1]>>[Cl:1][c:2]1[cH:3][n:4][c:5]([N:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[c:12]([Cl:13])[n:14]1 | Clc1nccnc1N1CCNCC1.O=C1CCC(=O)N1Cl | Clc1cnc(N2CCNCC2)c(Cl)n1 | null | null | C(Cl)(Cl)Cl | Functional Group Interconversion | Chlorination | bc1f7cfdae813ebe8c69faae7323293eaef048ef481216eb2be3204f184b46ec | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1cnc(N2CCNCC2)cn1 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#7;a:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[cH;D2;+0:7]:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:7]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 45 | [{"value": 45.0, "product": "ClC=1C(=NC=C(N1)Cl)N1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.7, "product": "ClC=1C(=NC=C(N1)Cl)N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 2-chloro-3-(1-piperazinyl)pyrazine (11.7 g, 58.7 mmol; from Example 90, Step 1) in CHCl3 (50 mL) was N-chlorosuccinimid (14.4 g, 108 mmol) added and the mixture was heated at reflux for 30 minutes. The reaction mixture was cooled to ambient temperature and extracted twice with water. The combined aqu... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1cnccn1.C1CCNC1 | c1cnccn1 | c1cnccn1.C1C[NH]CCN1 | HO- | C(Cl)(Cl)Cl | null | null | Clc1nccnc1N1CCNCC1.O=C1CCC(=O)N1Cl>C(Cl)(Cl)Cl>Clc1cnc(N2CCNCC2)c(Cl)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-310dc38479534f7198d45f099cab02c6 | BrBr.Clc1nccnc1N1CCNCC1>>Clc1nc(Br)cnc1N1CCNCC1 | O.ClC1=NC=CN=C1N1CCNCC1.C(=O)([O-])[O-].[Na+].[Na+].BrBr>>BrC=1N=C(C(=NC1)N1CCNCC1)Cl | Br[Br:5].[Cl:1][c:2]1[n:3][cH:4][cH:6][n:7][c:8]1[N:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1>>[Cl:1][c:2]1[n:3][c:4]([Br:5])[cH:6][n:7][c:8]1[N:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1 | BrBr.Clc1nccnc1N1CCNCC1 | Clc1nc(Br)cnc1N1CCNCC1 | null | null | CC(=O)O | Functional Group Interconversion | Bromination | 529a0f9fe0da45cfa7c46547368acdfd85f734daceed90047c4d46b62c2ed687 | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1cnc(N2CCNCC2)cn1 | Br-[Br;H0;D1;+0:1].[#7;a:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[cH;D2;+0:7]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:7]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 89.2 | [{"value": 89.0, "product": "BrC=1N=C(C(=NC1)N1CCNCC1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.2, "product": "BrC=1N=C(C(=NC1)N1CCNCC1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a mixture of 2-chloro-3-(1-piperazinyl)pyrazine (5.94 g, 30 mmol, from Example 90, Step 1) and Na2CO3 (6.0 g, 57 mmol) in AcOH (25 mL) was added a solution of Br2 (6.00 g 38.0 mmol) in AcOH (25 mL) dropwise at room temperature. The reaction mixture was stirred overnight. Water (50 mL) was added and the solution was ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cnccn1 | c1cnccn1 | c1cnccn1.C1C[NH]CCN1 | HBr | CC(=O)O | null | 8 | BrBr.Clc1nccnc1N1CCNCC1>CC(=O)O>Clc1nc(Br)cnc1N1CCNCC1 |
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