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-03ba810b7f464a06b5d8787af2e8b64e | ord-a881f7fabe29446d94622d478d282695 | CC(C)N1CCN(C(=O)c2cnc(Cl)n2C)CC1.Cc1ccccc1B(O)O>>Cc1ccccc1-c1ncc(C(=O)N2CCN(C(C)C)CC2)n1C | [O-]P(=O)([O-])[O-].[K+].[K+].[K+].C1(=C(C=CC=C1)B(O)O)C.ClC1=NC=C(N1C)C(=O)N1CCN(CC1)C(C)C>>C(C)(C)N1CCN(CC1)C(=O)C=1N(C(=NC1)C1=C(C=CC=C1)C)C | Cl[c:8]1[n:9][cH:10][c:11]([C:12](=[O:13])[N:14]2[CH2:15][CH2:16][N:17]([CH:18]([CH3:19])[CH3:20])[CH2:21][CH2:22]2)[n:23]1[CH3:24].OB(O)[c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[n:9][cH:10][c:11]([C:12](=[O:13])[N:14]2[CH2:15][CH2:16][N:17]([CH:18]([CH3:19])[CH3:... | CC(C)N1CCN(C(=O)c2cnc(Cl)n2C)CC1.Cc1ccccc1B(O)O | Cc1ccccc1-c1ncc(C(=O)N2CCN(C(C)C)CC2)n1C | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C1(=CC=CC=C1)C | C-C Coupling | Suzuki coupling with boronic acids | ce1cab4967c1a0f6f99d4e333791783eedefe86bb34f4a4690c2f95ed6598bd8 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=C(c1cnc(-c2ccccc2)[nH]1)N1CCNCC1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](-[C:5](-[#7:6])=[O;D1;H0:7]):[#7;a:8]:1-[C;D1;H3:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13](-[C;D1;H3:14]):[c:15]>>[#7:6]-[C:5](=[O;D1;H0:7])-[c:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13](-[C;D1;H3:14]):[c:15]):[#7;a:8]:1-[C;D1;H3:9] | null | [] | 100 | CELSIUS | 16 | HOUR | A reaction vessel is charged with Pd2(dba)3 (0.0183 g, 0.02 mmol), P(t-Bu)3HBF4 (0.0116 g, 0.04 mmol), K3PO4 (0.127 g, 0.60 mmol), o-tolylboronic acid (0.0408 g, 0.30 mmol) and (2-chloro-3-methyl-3H-imidazol-4-yl)-(4-isopropyl-piperazin-1-yl)-methanone (0.0542 g, 0.20 mmol). Toluene (2.4 mL, anhydrous) is added and the... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1c[nH]cn1.c1ccccc1 | c1ccccc1.c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1.C1C[NH]CC[NH]1 | HCl.B | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C | 100 | 16 | CC(C)N1CCN(C(=O)c2cnc(Cl)n2C)CC1.Cc1ccccc1B(O)O>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C1(=CC=CC=C1)C>Cc1ccccc1-c1ncc(C(=O)N2CCN(C(C)C)CC2)n1C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8b22fd99aea743d896a2430827fb4c7c | CC(C)N1CCCNCC1.OCc1cnc(-c2ccccc2F)[nH]1>>CC(C)N1CCCN(Cc2cnc(-c3ccccc3F)[nH]2)CC1 | FC1=C(C=CC=C1)C=1NC(=CN1)CO.C(C)(C)N1CCNCCC1>>FC1=C(C=CC=C1)C=1NC(=CN1)CN1CCN(CCC1)C(C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH2:7][NH:8][CH2:22][CH2:23]1.O[CH2:9][c:10]1[cH:11][n:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[F:20])[nH:21]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[CH2:5][CH2:6][CH2:7][N:8]([CH2:9][c:10]2[cH:11][n:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]3[F:20])[nH:21]2)[CH2... | CC(C)N1CCCNCC1.OCc1cnc(-c2ccccc2F)[nH]1 | CC(C)N1CCCN(Cc2cnc(-c3ccccc3F)[nH]2)CC1 | null | null | O=S(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | a7ea0b0d55fb0c7c14cafdf733d29854813a33bc3c453bf4a4c1ad47653fab35 | 87693a475e46c41583976158ec46dcaf8be8cc05c5635654a6a68033770f8d5c | c1ccc(-c2ncc(CN3CCCNCC3)[nH]2)cc1 | O-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1.[#7:7]-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[#7:7]-[C:8]-[C:9]-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1)-[C:11]-[C:12] | null | [] | 65 | CELSIUS | 1 | HOUR | [2-(2-Fluorophenyl)-1H-imidazol-5-yl]methyl alcohol (69 mg, 0.36 mmol, prepared essentially as described in PCT International Publication No. WO 96/16040) is dissolved in SOCl2 (4 mL) and stirred at 65° C. for 1 hr. The reaction mixture is cooled to rt then concentrated in vacuo. The residue is dissolved in toluene, an... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | C1C[NH]CCNC1 | C1C[NH]CC[NH]C1 | C1C[NH]CC[NH]C1.c1c[nH]cn1.c1ccccc1 | HO- | O=S(Cl)Cl | 65 | 1 | CC(C)N1CCCNCC1.OCc1cnc(-c2ccccc2F)[nH]1>O=S(Cl)Cl>CC(C)N1CCCN(Cc2cnc(-c3ccccc3F)[nH]2)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-84ab61881c3f4d459047f990649b7d88 | CCOC(=O)c1nc(C)cs1.O=C1CCC(=O)N1Br>>CCOC(=O)c1nc(C)c(Br)s1 | C1CC(=O)N(C1=O)Br.C(C)OC(=O)C=1SC=C(N1)C.C1CC(=O)N(C1=O)Br>>C(C)OC(=O)C=1SC(=C(N1)C)Br | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([CH3:9])[cH:10][s:12]1.O=C1CCC(=O)N1[Br:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([CH3:9])[c:10]([Br:11])[s:12]1 | CCOC(=O)c1nc(C)cs1.O=C1CCC(=O)N1Br | CCOC(=O)c1nc(C)c(Br)s1 | null | null | C(C)#N | Functional Group Interconversion | Bromination | 3505c5a135ac37e3769ac5551611b02e62ded9217a3618731c0104022c0bad49 | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | c1cscn1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[#16;a:6]:[cH;D2;+0:7]:[c:8](-[C;D1;H3:9]):[#7;a:10]:1>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]1:[#16;a:6]:[c;H0;D3;+0:7](-[Br;H0;D1;+0:1]):[c:8](-[C;D1;H3:9]):[#7;a:10]:1 | null | [] | null | null | 2 | HOUR | To a solution of 4-methyl-thiazole-2-carboxylic acid ethyl ester (171 mg, 1.0 mmol) in acetonitrile (5 ml) is added NBS (180 mg, 1.0 mmol). The reaction mixture is stirred at rt for 2 hr followed by the addition of a second portion of NBS (180 mg, 1.0 mmol). After stirring at rt for 3 hr, the solvent is removed. The re... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1cscn1.C1CCNC1 | c1cscn1 | c1cscn1 | HO- | C(C)#N | null | 2 | CCOC(=O)c1nc(C)cs1.O=C1CCC(=O)N1Br>C(C)#N>CCOC(=O)c1nc(C)c(Br)s1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-9f1c3eae5e914686a5941e976dd60d69 | CCOC(=O)c1nc(C)c(Br)s1.OB(O)c1cccc2ccccc12>>CCOC(=O)c1nc(C)c(-c2cccc3ccccc23)s1 | C(C)OC(=O)C=1SC(=C(N1)C)Br.C1(=CC=CC2=CC=CC=C12)B(O)O.C([O-])([O-])=O.[Cs+].[Cs+]>>C(C)OC(=O)C=1SC(=C(N1)C)C1=CC=CC2=CC=CC=C12 | Br[c:10]1[c:8]([CH3:9])[n:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[s:21]1.OB(O)[c:11]1[cH:12][cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([CH3:9])[c:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)[s:21]1 | CCOC(=O)c1nc(C)c(Br)s1.OB(O)c1cccc2ccccc12 | CCOC(=O)c1nc(C)c(-c2cccc3ccccc23)s1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | O1CCOCC1 | C-C Coupling | OtherReaction | 38230c1273a69eec205027790ccd7ed227c21bd62e48400f1fb43e23d949bdb1 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc2c(-c3cncs3)cccc2c1 | Br-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3](-[C:4](-[#8:5])=[O;D1;H0:6]):[#7;a:7]:[c:8]:1-[C;D1;H3:9].O-B(-O)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13](:[c:14]):[c:15]>>[#8:5]-[C:4](=[O;D1;H0:6])-[c:3]1:[#16;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13](:[c:14]):[c:15]):[c:8](-[C;D1;H3:9]):[#7;a:7]:1 | null | [] | 110 | CELSIUS | 8 | HOUR | To a solution of 5-bromo-4-methyl-thiazole-2-carboxylic acid ethyl ester (60 mg, 0.24 mmol) in 1,4-dioxane (2 ml) is added 1-naphthaleneboronic acid (50 mg, 0.29 mmol), cesium carbonate (187 mg, 0.58 mmol) and Pd(PPh3)4 (28 mg, 0.024 mmol). The reaction mixture is stirred in a sealed tube at 110° C. overnight. After co... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1cscn1.c1ccc2ccccc2c1 | c1cscn1.c1ccc2ccccc2c1 | c1cscn1.c1ccc2ccccc2c1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1 | 110 | 8 | CCOC(=O)c1nc(C)c(Br)s1.OB(O)c1cccc2ccccc12>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.O1CCOCC1>CCOC(=O)c1nc(C)c(-c2cccc3ccccc23)s1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a99f6adcd06645219a6b3df332299ba2 | CCOC(=O)c1nc(C)c(-c2cccc3ccccc23)s1>>Cc1nc(C(=O)O)sc1-c1cccc2ccccc12 | C(C)OC(=O)C=1SC(=C(N1)C)C1=CC=CC2=CC=CC=C12.[OH-].[Na+]>>CC=1N=C(SC1C1=CC=CC2=CC=CC=C12)C(=O)O | CC[O:7][C:5]([c:4]1[n:3][c:2]([CH3:1])[c:9](-[c:10]2[cH:11][cH:12][cH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]23)[s:8]1)=[O:6]>>[CH3:1][c:2]1[n:3][c:4]([C:5](=[O:6])[OH:7])[s:8][c:9]1-[c:10]1[cH:11][cH:12][cH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12 | CCOC(=O)c1nc(C)c(-c2cccc3ccccc23)s1 | Cc1nc(C(=O)O)sc1-c1cccc2ccccc12 | null | null | C1CCOC1.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(-c3cncs3)cccc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#16;a:5]):[#7;a:6]>>[#16;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[#7;a:6] | null | [] | null | null | 1 | HOUR | To a solution of 4-methyl-5-naphthalen-1-yl-thiazole-2-carboxylic acid ethyl ester (30 mg, 0.10 mmol) in water (1 ml) and THF (1 ml) is added sodium hydroxide (0.2 mL, 1M, 0.20 mmol). The reaction mixture is stirred at rt for 1 hr, and then extracted with ethyl ether (30 mL). The aqueous layer is acidified to pH<7.0 by... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cscn1.c1ccc2ccccc2c1 | Other | C1CCOC1.O | null | 1 | CCOC(=O)c1nc(C)c(-c2cccc3ccccc23)s1>C1CCOC1.O>Cc1nc(C(=O)O)sc1-c1cccc2ccccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1fd45a014550457f9029f2a892cfb77e | CC(C)N1CCNCC1.Cc1nc(C(=O)O)sc1-c1cccc2ccccc12>>Cc1nc(C(=O)N2CCN(C(C)C)CC2)sc1-c1cccc2ccccc12 | CC=1N=C(SC1C1=CC=CC2=CC=CC=C12)C(=O)O.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C)(C)N1CCNCC1.CCN(CC)CC>>C(C)(C)N1CCN(CC1)C(=O)C=1SC(=C(N1)C)C1=CC=CC2=CC=CC=C12 | [NH:7]1[CH2:8][CH2:9][N:10]([CH:11]([CH3:12])[CH3:13])[CH2:14][CH2:15]1.O[C:5]([c:4]1[n:3][c:2]([CH3:1])[c:17](-[c:18]2[cH:19][cH:20][cH:21][c:22]3[cH:23][cH:24][cH:25][cH:26][c:27]23)[s:16]1)=[O:6]>>[CH3:1][c:2]1[n:3][c:4]([C:5](=[O:6])[N:7]2[CH2:8][CH2:9][N:10]([CH:11]([CH3:12])[CH3:13])[CH2:14][CH2:15]2)[s:16][c:17]... | CC(C)N1CCNCC1.Cc1nc(C(=O)O)sc1-c1cccc2ccccc12 | Cc1nc(C(=O)N2CCN(C(C)C)CC2)sc1-c1cccc2ccccc12 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ncc(-c2cccc3ccccc23)s1)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#16;a:4]:[c:5]:[c:6]:[#7;a:7]:1.[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1)-[c:3]1:[#16;a:4]:[c:5]:[c:6]:[#7;a:7]:1 | null | [] | null | null | 2 | HOUR | To a solution of 4-methyl-5-naphthalen-1-yl-thiazole-2-carboxylic acid in methylene chloride (2 ml) is added BOP (44 mg, 0.10 mmol), isopropylpiperazine (13 mg, 0.10 mmol) and Et3N (20 mg, 0.20 mmol). The reaction mixture is stirred at rt for 2 hr. Solvent is removed and the resulting mixture is purified by PTLC to giv... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1cscn1.C1C[NH]CC[NH]1.c1ccc2ccccc2c1 | HO- | C(Cl)Cl | null | 2 | CC(C)N1CCNCC1.Cc1nc(C(=O)O)sc1-c1cccc2ccccc12>C(Cl)Cl>Cc1nc(C(=O)N2CCN(C(C)C)CC2)sc1-c1cccc2ccccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-46dcf18ec7cf41598714200c3bd40942 | Brc1nc(Br)c(Br)[nH]1.CCI>>CCn1c(Br)nc(Br)c1Br | [H-].[Na+].BrC=1NC(=C(N1)Br)Br.ICC>>BrC=1N(C(=C(N1)Br)Br)CC | [nH:3]1[c:4]([Br:5])[n:6][c:7]([Br:8])[c:9]1[Br:10].I[CH2:2][CH3:1]>>[CH3:1][CH2:2][n:3]1[c:4]([Br:5])[n:6][c:7]([Br:8])[c:9]1[Br:10] | Brc1nc(Br)c(Br)[nH]1.CCI | CCn1c(Br)nc(Br)c1Br | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1c[nH]cn1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[Br;D1;H0:3]-[c:4]1:[nH;D2;+0:5]:[c:6](-[Br;D1;H0:7]):[#7;a:8]:[c:9]:1-[Br;D1;H0:10]>>[Br;D1;H0:3]-[c:4]1:[c:9](-[Br;D1;H0:10]):[#7;a:8]:[c:6](-[Br;D1;H0:7]):[n;H0;D3;+0:5]:1-[CH2;D2;+0:1]-[C;D1;H3:2] | null | [] | 50 | CELSIUS | 1 | HOUR | To a suspension of sodium hydride (2.40 g, 60% mineral oil suspension, 60 mmol) in anhydrous DMF (50 ml) is added a solution of 2,4,5-tribromoimidazole (15.09 g, 50 mmol) in DMF (30 ml) at rt. The resulting mixture is stirred at 50° C. for 1 hr, and then cooled to 0° C., followed by the dropwise addition of iodoethane ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1 | HI | CN(C)C=O | 50 | 1 | Brc1nc(Br)c(Br)[nH]1.CCI>CN(C)C=O>CCn1c(Br)nc(Br)c1Br |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-707e734d43db4ad18a4482477ac34ea0 | CCn1c(Br)nc(Br)c1Br.OB(Oc1cccc2ccccc12)c1ccccc1>>CCn1c(-c2cccc3ccccc23)nc(Br)c1Br | BrC=1N(C(=C(N1)Br)Br)CC.C1(=CC=CC2=CC=CC=C12)OB(O)C1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+]>>BrC=1N=C(N(C1Br)CC)C1=CC=CC2=CC=CC=C12 | Br[c:4]1[n:3]([CH2:2][CH3:1])[c:18]([Br:19])[c:16]([Br:17])[n:15]1.OB(O[c:5]1[cH:6][cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12)c1ccccc1>>[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[n:15][c:16]([Br:17])[c:18]1[Br:19] | CCn1c(Br)nc(Br)c1Br.OB(Oc1cccc2ccccc12)c1ccccc1 | CCn1c(-c2cccc3ccccc23)nc(Br)c1Br | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 1e4b1876d7dd5c6837ce8a1dd3cb5cd6aa9f3a18e5846c4c841270b23816f12e | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1ccc2c(-c3ncc[nH]3)cccc2c1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:1-[C:6].O-B(-O-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](:[c:11]):[c:12])-c1:c:c:c:c:c:1>>[C:6]-[#7;a:5]1:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10](:[c:11]):[c:12] | null | [] | 90 | CELSIUS | 16 | HOUR | To a solution of 2,4,5-tribromo-1-ethyl-1H-imidazole (13.19 g, 40 mmol) and 1-naphthylphenylboronic acid (6.88 g, 40 mmol, 1.0 eq.) in toluene (100 ml) is added aqueous potassium carbonate solution (2.0 N, 40 ml, 2.0 eq.), followed by the addition of Pd(PPh3)4 (1.154 g, 1 mmol, 0.025 eq.). The resulting mixture is dega... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1ccc2ccccc2c1.c1ccccc1 | c1c[nH]cn1.c1ccc2ccccc2c1 | c1c[nH]cn1.c1ccc2ccccc2c1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C | 90 | 16 | CCn1c(Br)nc(Br)c1Br.OB(Oc1cccc2ccccc12)c1ccccc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C>CCn1c(-c2cccc3ccccc23)nc(Br)c1Br |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a8f3af09900c4770b3608276e00844f6 | CCn1c(-c2cccc3ccccc23)nc(Br)c1Br.CN(C)C=O>>CCn1cc(C=O)nc1-c1cccc2ccccc12 | C[Si](C)(C)Cl.CN(C)C=O.BrC=1N=C(N(C1Br)CC)C1=CC=CC2=CC=CC=C12.[Li]CCCC.CCCCCC.[Li]CCCC.CCCCCC>>C(C)N1C(=NC(=C1)C=O)C1=CC=CC2=CC=CC=C12 | Br[c:4]1[n:3]([CH2:2][CH3:1])[c:9](-[c:10]2[cH:11][cH:12][cH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]23)[n:8][c:5]1Br.CN(C)[CH:6]=[O:7]>>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([CH:6]=[O:7])[n:8][c:9]1-[c:10]1[cH:11][cH:12][cH:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12 | CCn1c(-c2cccc3ccccc23)nc(Br)c1Br.CN(C)C=O | CCn1cc(C=O)nc1-c1cccc2ccccc12 | null | null | CO.C1CCOC1.O | C-C Coupling | OtherReaction | 9af6f9293276ec09762e7d33d47452238683ac4d42196c8b23ccaf7c6c11e003 | d9c4461141b547f59eb6421e79e298156f74861075f2c22966c0a28a10b10c96 | c1ccc2c(-c3ncc[nH]3)cccc2c1 | Br-[c;H0;D3;+0:1]1:[#7;a:2](-[C:3]):[c:4](-[c:5]):[#7;a:6]:[c;H0;D3;+0:7]:1-Br.C-N(-C)-[CH;D2;+0:8]=[O;D1;H0:9]>>[C:3]-[#7;a:2]1:[cH;D2;+0:1]:[c;H0;D3;+0:7](-[CH;D2;+0:8]=[O;D1;H0:9]):[#7;a:6]:[c:4]:1-[c:5] | null | [] | -78 | CELSIUS | 1 | HOUR | To a solution of 4,5-dibromo-1-ethyl-2-naphthalen-1-yl-1H-imidazole (3.80 g, 10 mmol) in anhydrous THF (60 ml) at −78° C. under nitrogen is added a solution of n-BuLi in hexane (1.6 M, 6.88 ml, 11 mmol, 1.1 eq.) dropwise. The resulting mixture is stirred at −78° C. for 1 hr, followed by dropwise addition of TMSCl (1.18... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Tertiary amide | Aldehyde | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccc2ccccc2c1 | HBr | CO.C1CCOC1.O | -78 | 1 | CCn1c(-c2cccc3ccccc23)nc(Br)c1Br.CN(C)C=O>CO.C1CCOC1.O>CCn1cc(C=O)nc1-c1cccc2ccccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-8d1cd2d6e27b4b369888a3d951b36078 | CCOc1ccc2ccccc2c1-c1ncc(C=O)n1COC>>CCOc1ccc2ccccc2c1-c1ncc(C=O)[nH]1 | C(C)OC1=C(C2=CC=CC=C2C=C1)C1=NC=C(N1COC)C=O.Cl>>C(C)OC1=C(C2=CC=CC=C2C=C1)C1=NC=C(N1)C=O | COC[n:20]1[c:14](-[c:13]2[c:4]([O:3][CH2:2][CH3:1])[cH:5][cH:6][c:7]3[cH:8][cH:9][cH:10][cH:11][c:12]32)[n:15][cH:16][c:17]1[CH:18]=[O:19]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][cH:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[c:13]1-[c:14]1[n:15][cH:16][c:17]([CH:18]=[O:19])[nH:20]1 | CCOc1ccc2ccccc2c1-c1ncc(C=O)n1COC | CCOc1ccc2ccccc2c1-c1ncc(C=O)[nH]1 | null | null | O1CCOCC1 | Reduction | OtherReaction | c2dcbe9d831e37c9851593e99e077458c2c2bd822601c7bc7ae4afe468a8014c | 84394d34c591024a84d9393eb3e8adb8ada5a6225c3abafc4dae9aedd4568be4 | c1ccc2c(-c3ncc[nH]3)cccc2c1 | C-O-C-[n;H0;D3;+0:1]1:[c:2](-[c:3]):[#7;a:4]:[c:5]:[c:6]:1-[C:7]=[O;D1;H0:8]>>[O;D1;H0:8]=[C:7]-[c:6]1:[c:5]:[#7;a:4]:[c:2](-[c:3]):[nH;D2;+0:1]:1 | null | [] | 80 | CELSIUS | 3 | HOUR | To a solution of 2-(2-ethoxy-naphthalen-1-yl)-3-methoxymethyl-3H-imidazole-4-carbaldehyde (prepared as described for 1-ethyl-2-naphthalen-1-yl-1H-imidazole-4-carbaldehyde illustrated in example 2.F) (2.4 g, 7.4 mmol) in dioxane (30 ml) is added 6.0 N hydrochloric acid (10 ml). The resulting mixture is stirred at 80° C.... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1cnc[nH]1 | c1c[nH]cn1 | c1ccc2ccccc2c1.c1c[nH]cn1 | HO- | O1CCOCC1 | 80 | 3 | CCOc1ccc2ccccc2c1-c1ncc(C=O)n1COC>O1CCOCC1>CCOc1ccc2ccccc2c1-c1ncc(C=O)[nH]1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2b9f425e2c714e618d94b5bb6d3af4c4 | CCOC(=O)OCC.CCn1c(-c2cccc3ccccc23)nc(Br)c1Br>>CCOC(=O)c1cn(CC)c(-c2cccc3ccccc23)n1 | BrC=1N=C(N(C1Br)CC)C1=CC=CC2=CC=CC=C12.[Li]CCCC.CCCCCC.[Li]CCCC.CCCCCC.Cl[Si](C)(C)C.C(OCC)(OCC)=O.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(C)OC(=O)C=1N=C(N(C1)CC)C1=CC=CC2=CC=CC=C12 | CCO[C:4]([O:3][CH2:2][CH3:1])=[O:5].Br[c:6]1[c:7](Br)[n:8]([CH2:9][CH3:10])[c:11](-[c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]23)[n:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8]([CH2:9][CH3:10])[c:11](-[c:12]2[cH:13][cH:14][cH:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]23)[n:22]1 | CCOC(=O)OCC.CCn1c(-c2cccc3ccccc23)nc(Br)c1Br | CCOC(=O)c1cn(CC)c(-c2cccc3ccccc23)n1 | null | null | C1CCOC1.O | C-C Coupling | OtherReaction | 1884e22398b71b80056168b5b49cb39632cc01fe6aef2cf776dc7828546cc3c4 | 850228b587f13401a2131f8a953feaad6e5b5201ccc2bd72a0da57c6c2c84ed9 | c1ccc2c(-c3ncc[nH]3)cccc2c1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5](-[C:6]):[c;H0;D3;+0:7]:1-Br.C-C-O-[C;H0;D3;+0:8](=[O;D1;H0:9])-[#8:10]-[C:11]>>[C:11]-[#8:10]-[C;H0;D3;+0:8](=[O;D1;H0:9])-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5](-[C:6]):[cH;D2;+0:7]:1 | null | [] | -78 | CELSIUS | 1 | HOUR | To a solution of 4,5-dibromo-1-ethyl-2-naphthalen-1-yl-1H-imidazole (3.80 g, 10 mmol) in anhydrous THF (60 ml) at −78° C. under nitrogen is added a solution of n-BuLi in hexane (1.6 M, 6.88 ml, 11 mmol, 1.1 eq.) dropwise. The resulting mixture is stirred at −78° C. for 1 hr, after which chlorotrimethylsilane (1.188 g, ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carbonic Ester | Ester | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccc2ccccc2c1 | HBr | C1CCOC1.O | -78 | 1 | CCOC(=O)OCC.CCn1c(-c2cccc3ccccc23)nc(Br)c1Br>C1CCOC1.O>CCOC(=O)c1cn(CC)c(-c2cccc3ccccc23)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e1d19fefd1aa46a38ad1627104fb90fd | CCOC(=O)c1cn(CC)c(-c2cccc3ccccc23)n1>>CCn1cc(C(=O)O)nc1-c1cccc2ccccc12 | C(C)OC(=O)C=1N=C(N(C1)CC)C1=CC=CC2=CC=CC=C12.[OH-].[Li+]>>C(C)N1C(=NC(=C1)C(=O)O)C1=CC=CC2=CC=CC=C12 | CC[O:8][C:6]([c:5]1[cH:4][n:3]([CH2:2][CH3:1])[c:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)[n:9]1)=[O:7]>>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[n:9][c:10]1-[c:11]1[cH:12][cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12 | CCOC(=O)c1cn(CC)c(-c2cccc3ccccc23)n1 | CCn1cc(C(=O)O)nc1-c1cccc2ccccc12 | null | null | C1CCOC1.O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(-c3ncc[nH]3)cccc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[#7;a:5] | null | [] | 50 | CELSIUS | null | null | 1-Ethyl-2-naphthalen-1-yl-1H-imidazole-4-carboxylic acid ethyl ester (2.2 g, 7.48 mmol) is dissolved in THF (20 ml), followed by the addition of aqueous lithium hydroxide solution (2.0 N, 7.5 ml, 2.0 eq.). The mixture is heated at 50° C. overnight. THF is stripped off under reduced pressure, and the residue is diluted ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1c[nH]cn1.c1ccc2ccccc2c1 | Other | C1CCOC1.O | 50 | null | CCOC(=O)c1cn(CC)c(-c2cccc3ccccc23)n1>C1CCOC1.O>CCn1cc(C(=O)O)nc1-c1cccc2ccccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-80f85a55b5bb42a9b5fddbc41a2802c1 | CCI.c1ccc2c(-c3ncc[nH]3)cccc2c1>>CCn1ccnc1-c1cccc2ccccc12 | [H-].[Na+].C1(=CC=CC2=CC=CC=C12)C=1NC=CN1.ICC>>C(C)N1C(=NC=C1)C1=CC=CC2=CC=CC=C12 | I[CH2:2][CH3:1].[nH:3]1[cH:4][cH:5][n:6][c:7]1-[c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[CH3:1][CH2:2][n:3]1[cH:4][cH:5][n:6][c:7]1-[c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12 | CCI.c1ccc2c(-c3ncc[nH]3)cccc2c1 | CCn1ccnc1-c1cccc2ccccc12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 5118ce9eea46859cccf16d01cf8151757afd816de0c93fe6fcb74a0ee15c5a67 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc2c(-c3ncc[nH]3)cccc2c1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[c:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[nH;D2;+0:8]:1>>[C;D1;H3:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[c:7]:[c:6]:[#7;a:5]:[c:4]:1-[c:3] | null | [] | 50 | CELSIUS | 1 | HOUR | To a suspension of sodium hydride (2.40 g, 60% mineral oil suspension, 60 mmol) in anhydrous DMF (30 ml) is added a solution of 2-naphthalen-1-yl-1H-imidazole (9.70 g, 50 mmol) in DMF (70 ml) at rt. The resulting mixture is stirred at 50° C. for 1 hr, and then cooled to 0° C., after which iodoethane (8.19 g, 52.5 mmol,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1ncc[nH]1 | c1ncc[nH]1.c1ccc2ccccc2c1 | HI | CN(C)C=O | 50 | 1 | CCI.c1ccc2c(-c3ncc[nH]3)cccc2c1>CN(C)C=O>CCn1ccnc1-c1cccc2ccccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2a1bb3c7e7b748988571efc43482488c | CCOC(=O)OCC.CCn1ccnc1-c1cccc2ccccc12>>CCOC(=O)c1cnc(-c2cccc3ccccc23)n1CC | C(OCC)(OCC)=O.C(C)N1C(=NC=C1)C1=CC=CC2=CC=CC=C12.[Li]CCCC.CCCCCC>>C(C)OC(=O)C=1N(C(=NC1)C1=CC=CC2=CC=CC=C12)CC | CCO[C:4]([O:3][CH2:2][CH3:1])=[O:5].[cH:6]1[cH:7][n:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]23)[n:20]1[CH2:21][CH3:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][c:14]3[cH:15][cH:16][cH:17][cH:18][c:19]23)[n:20]1[CH2:21][CH3:22] | CCOC(=O)OCC.CCn1ccnc1-c1cccc2ccccc12 | CCOC(=O)c1cnc(-c2cccc3ccccc23)n1CC | null | null | C1CCOC1.O | C-C Coupling | Friedel-Crafts acylation | 81f148e084f1dd3db2054da155451057eb8681cac5b90e511cba933650fa3985 | 372f84de287e46e8e402e2fc0f416c45846439cb3eb957465fe2464b708bdd7f | c1ccc2c(-c3ncc[nH]3)cccc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[#7;a:6]1:[cH;D2;+0:7]:[c:8]:[#7;a:9]:[c:10]:1-[c:11]>>[C:5]-[#7;a:6]1:[c:10](-[c:11]):[#7;a:9]:[c:8]:[c;H0;D3;+0:7]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | null | [] | -78 | CELSIUS | 1 | HOUR | To a solution of 1-ethyl-2-naphthalen-1-yl-1H-imidazole (1.11 g, 5 mmol) in anhydrous THF (30 ml) at −78° C. under nitrogen is added a solution of n-BuLi in hexane (1.6 M, 3.44 ml, 5.5 mmol, 1.1 eq.) dropwise. The resulting mixture is stirred at −78° C. for 1 hr, followed by the addition of diethyl carbonate (1.77 g, 1... | 10.6084/m9.figshare.5104873.v1 | null | Carbonic Ester | Ester | c1ncc[nH]1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccc2ccccc2c1 | HO- | C1CCOC1.O | -78 | 1 | CCOC(=O)OCC.CCn1ccnc1-c1cccc2ccccc12>C1CCOC1.O>CCOC(=O)c1cnc(-c2cccc3ccccc23)n1CC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7e7002a68c61423684a943412eae5f7c | CCN(CC)CC.CCn1c(C(=O)O)cnc1-c1cccc2ccccc12.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C>>CCn1c(C(=O)N2CCN(C3CCC3)CC2)cnc1-c1cccc2ccccc12 | F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C)N1C(=NC=C1C(=O)O)C1=CC=CC2=CC=CC=C12.CCN(CC)CC>>C1(CCC1)N1CCN(CC1)C(=O)C=1N(C(=NC1)C1=CC=CC2=CC=CC=C12)CC | [CH3:8][CH2:9][N:10]([CH2:11][CH3:12])[CH2:15][CH3:16].O[C:5]([c:4]1[n:3]([CH2:2][CH3:1])[c:19](-[c:20]2[cH:21][cH:22][cH:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]23)[n:18][cH:17]1)=[O:6].CN(C)[P+](On1n[n:7]c2cc[cH:13][cH:14]c21)(N(C)C)N(C)C>>[CH3:1][CH2:2][n:3]1[c:4]([C:5](=[O:6])[N:7]2[CH2:8][CH2:9][N:10]([CH:11]3... | CCN(CC)CC.CCn1c(C(=O)O)cnc1-c1cccc2ccccc12.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C | CCn1c(C(=O)N2CCN(C3CCC3)CC2)cnc1-c1cccc2ccccc12 | null | null | C(Cl)Cl | Acylation | OtherReaction | 69ee77d23b05939e46a0f531d3c7c366c2e80e0a094236d12c3e891cd946cbde | 76edb1f56d3da33321282224061a3172c17caed194f0edd7470584306a88361e | O=C(c1cnc(-c2cccc3ccccc23)[nH]1)N1CCN(C2CCC2)CC1 | C-N(-C)-[P+](-O-n1:n:[n;H0;D2;+0:1]:c2:c:c:[cH;D2;+0:2]:[cH;D2;+0:3]:c:2:1)(-N(-C)-C)-N(-C)-C.O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6]1:[c:7]:[#7;a:8]:[c:9]:[#7;a:10]:1-[C:11].[CH3;D1;+0:12]-[CH2;D2;+0:13]-[#7:14](-[C:15]-[CH3;D1;+0:16])-[C:17]-[CH3;D1;+0:18]>>[C:11]-[#7;a:10]1:[c:9]:[#7;a:8]:[c:7]:[c:6]:1-[C;H0;D3;+0:4](=... | null | [] | null | null | 8 | HOUR | 3-Ethyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid (105 mg, 0.394 mmol) and 1-cyclobutylpiperazine bistrifluoroacetate (145 mg, 0.394 mmol, 1.0 eq.) are dissolved in DCM (5 ml), and to the solution is added Et3N (4 eq.), followed by BOP coupling regent (183 mg, 0.433 mmol, 1.1 eq.). The resulting mixture is stirr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amine.Tertiary amine.Tertiary amine | Tertiary amide | c1ccc2[nH]nnc2c1 | C1C[NH]CC[NH]1.C1CCC1 | c1cnc[nH]1.C1C[NH]CC[NH]1.C1CCC1.c1ccc2ccccc2c1 | HO- | C(Cl)Cl | null | 8 | CCN(CC)CC.CCn1c(C(=O)O)cnc1-c1cccc2ccccc12.CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C>C(Cl)Cl>CCn1c(C(=O)N2CCN(C3CCC3)CC2)cnc1-c1cccc2ccccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-712d0ca79ca34dd384a9ac7acc37c7c0 | CCCCCC.CCn1c(-c2cccc3ccccc23)nc(Cl)c1Cl.COC(=O)OC>>CCOC(=O)c1c(Cl)nc(-c2cccc3ccccc23)n1CC | C(OC)(OC)=O.ClC=1N=C(N(C1Cl)CC)C1=CC=CC2=CC=CC=C12.[Li]CCCC.CCCCCC>>C(C)OC(=O)C=1N(C(=NC1Cl)C1=CC=CC2=CC=CC=C12)CC | CCCCC[CH3:1].Cl[c:6]1[c:7]([Cl:8])[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)[n:21]1[CH2:22][CH3:23].CO[C:4]([O:3][CH3:2])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([Cl:8])[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)[n:21]1[CH2:... | CCCCCC.CCn1c(-c2cccc3ccccc23)nc(Cl)c1Cl.COC(=O)OC | CCOC(=O)c1c(Cl)nc(-c2cccc3ccccc23)n1CC | null | null | C1CCOC1.O | C-C Coupling | OtherReaction | 5e0dcd9c0f4140fbcb925d05ab74e6631c7d9f4da048ac90751b65562fffc238 | bcd3559e95d57605d0e6e7a6ba9cc016318f006dee2eacb538f0c39f9d5391eb | c1ccc2c(-c3ncc[nH]3)cccc2c1 | C-C-C-C-C-[CH3;D1;+0:1].C-O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[#8:4]-[CH3;D1;+0:5].Cl-[c;H0;D3;+0:6]1:[#7;a:7](-[C:8]):[c:9](-[c:10]):[#7;a:11]:[c:12]:1-[Cl;D1;H0:13]>>[C:8]-[#7;a:7]1:[c:9](-[c:10]):[#7;a:11]:[c:12](-[Cl;D1;H0:13]):[c;H0;D3;+0:6]:1-[C;H0;D3;+0:2](=[O;D1;H0:3])-[#8:4]-[CH2;D2;+0:5]-[CH3;D1;+0:1] | null | [] | -78 | CELSIUS | 1 | HOUR | To a solution of 4,5-dichloro-1-ethyl-2-naphthalen-1-yl-1H-imidazole (2.87 g, 9.86 mmol) in anhydrous THF (60 ml) at −78° C. under nitrogen is added a solution of n-BuLi in hexane (1.6 M, 6.78 ml, 10.84 mmol, 1.1 eq.) dropwise. The resulting mixture is stirred at −78° C. for 1 hr, followed by the addition of dimethyl c... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbonic Ester | Ester | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccc2ccccc2c1 | HCl | C1CCOC1.O | -78 | 1 | CCCCCC.CCn1c(-c2cccc3ccccc23)nc(Cl)c1Cl.COC(=O)OC>C1CCOC1.O>CCOC(=O)c1c(Cl)nc(-c2cccc3ccccc23)n1CC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-3784c7b763394a5792a6078a91210fb0 | CCOC(=O)c1c(Cl)nc(-c2cccc3ccccc23)n1CC>>CCn1c(-c2cccc3ccccc23)nc(Cl)c1C(=O)O | C1CCOC1.C(C)OC(=O)C=1N(C(=NC1Cl)C1=CC=CC2=CC=CC=C12)CC.C1CCOC1.[OH-].[Li+]>>ClC1=C(N(C(=N1)C1=CC=CC2=CC=CC=C12)CC)C(=O)O | CC[O:21][C:19]([c:18]1[n:3]([CH2:2][CH3:1])[c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[n:15][c:16]1[Cl:17])=[O:20]>>[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[n:15][c:16]([Cl:17])[c:18]1[C:19](=[O:20])[OH:21] | CCOC(=O)c1c(Cl)nc(-c2cccc3ccccc23)n1CC | CCn1c(-c2cccc3ccccc23)nc(Cl)c1C(=O)O | null | null | O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc2c(-c3ncc[nH]3)cccc2c1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[#7;a:5] | null | [] | 50 | CELSIUS | null | null | 5-Chloro-3-ethyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid ethyl ester (62 g, 35 mmol) is dissolved in. THF (10 ml), and aqueous lithium hydroxide solution (2.0 N, 6.35 ml, 2.0 eq.) is added. The mixture is heated at 50° C. overnight. THF is stripped off under reduced pressure, and the residue is diluted with wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1c[nH]cn1.c1ccc2ccccc2c1 | Other | O | 50 | null | CCOC(=O)c1c(Cl)nc(-c2cccc3ccccc23)n1CC>O>CCn1c(-c2cccc3ccccc23)nc(Cl)c1C(=O)O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-063302fd527f4632a4a26455de7386ac | CCn1c(-c2cccc3ccccc23)nc(Br)c1Br.C[Si](C)(C)Cl.O=S(=O)(c1ccccc1)N(F)S(=O)(=O)c1ccccc1>>CCn1c(-c2cccc3ccccc23)nc(F)c1[Si](C)(C)C | C[Si](C)(C)Cl.C1=CC=C(C=C1)S(=O)(=O)N(F)S(=O)(=O)C2=CC=CC=C2.BrC=1N=C(N(C1Br)CC)C1=CC=CC2=CC=CC=C12.[Li]CCCC.CCCCCC.[Li]CCCC.CCCCCC>>C(C)N1C(=NC(=C1[Si](C)(C)C)F)C1=CC=CC2=CC=CC=C12 | Br[c:16]1[n:15][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[n:3]([CH2:2][CH3:1])[c:18]1Br.Cl[Si:19]([CH3:20])([CH3:21])[CH3:22].O=S(=O)(c1ccccc1)N(S(=O)(=O)c1ccccc1)[F:17]>>[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[n:15][c:16]([F:17])[c:... | CCn1c(-c2cccc3ccccc23)nc(Br)c1Br.C[Si](C)(C)Cl.O=S(=O)(c1ccccc1)N(F)S(=O)(=O)c1ccccc1 | CCn1c(-c2cccc3ccccc23)nc(F)c1[Si](C)(C)C | null | null | C1CCOC1.O | Miscellaneous | OtherReaction | 56db6f3ed60a43dd039ce4d859f26cd02b3c839e21378a6dec6daf53b49464c7 | 7d719443a27bb0f615d6ac749cd29b4ae1c5b5ff710db8479ebd8b00984c881f | c1ccc2c(-c3ncc[nH]3)cccc2c1 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c:4]):[#7;a:5](-[C:6]):[c;H0;D3;+0:7]:1-Br.Cl-[Si;H0;D4;+0:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].O=S(=O)(-N(-[F;H0;D1;+0:12])-S(=O)(=O)-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:6]-[#7;a:5]1:[c:3](-[c:4]):[#7;a:2]:[c;H0;D3;+0:1](-[F;H0;D1;+0:12]):[c;H0;D3;+0:7]:1-[Si;H0;D4;+0:8](-[C;... | null | [] | -78 | CELSIUS | 1 | HOUR | To a solution of 4,5-dibromo-1-ethyl-2-naphthalen-1-yl-1H-imidazole (6.55 g, 17.2 mmol) in anhydrous THF (150 ml) at −78° C. under nitrogen is added a solution of n-BuLi in hexane (1.6 M, 11.8 ml, 19 mmol, 1.1 eq.) dropwise. The resulting mixture is stirred at −78° C. for 1 hr, and TMSCl (2.05 g, 19 mmol, 1.1 eq.) is a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Tertiary amine.Silyl protective group | Aromatic halide.Silyl protective group | c1c[nH]cn1.c1ccccc1.c1ccccc1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccc2ccccc2c1 | HCl.Br- | C1CCOC1.O | -78 | 1 | CCn1c(-c2cccc3ccccc23)nc(Br)c1Br.C[Si](C)(C)Cl.O=S(=O)(c1ccccc1)N(F)S(=O)(=O)c1ccccc1>C1CCOC1.O>CCn1c(-c2cccc3ccccc23)nc(F)c1[Si](C)(C)C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a55c86c65da04b15a979060a6498a635 | CCn1c(-c2cccc3ccccc23)nc(F)c1[Si](C)(C)C>>CCn1cc(F)nc1-c1cccc2ccccc12 | C(C)N1C(=NC(=C1[Si](C)(C)C)F)C1=CC=CC2=CC=CC=C12.O.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC>>C(C)N1C(=NC(=C1)F)C1=CC=CC2=CC=CC=C12 | C[Si](C)(C)[c:4]1[n:3]([CH2:2][CH3:1])[c:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[n:7][c:5]1[F:6]>>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([F:6])[n:7][c:8]1-[c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12 | CCn1c(-c2cccc3ccccc23)nc(F)c1[Si](C)(C)C | CCn1cc(F)nc1-c1cccc2ccccc12 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | c7f462886971c9302390ac232c55147304002681edbc6aa0690a17b1d7b7af67 | dc52a720480da1d65217db7d5178c684d09e72e99cbbe1f9f67cca818c9ff2e9 | c1ccc2c(-c3ncc[nH]3)cccc2c1 | C-[Si](-C)(-C)-[c;H0;D3;+0:1]1:[#7;a:2](-[C:3]):[c:4]:[#7;a:5]:[c:6]:1-[F;D1;H0:7]>>[C:3]-[#7;a:2]1:[c:4]:[#7;a:5]:[c:6](-[F;D1;H0:7]):[cH;D2;+0:1]:1 | null | [] | null | null | 4 | HOUR | Crude 1-ethyl-4-fluoro-2-naphthalen-1-yl-5-trimethylsilanyl-1H-imidazole (5.49 g) is dissolved in THF (75 ml), and to the solution is added tetrabutylammonium fluoride hydrate (5.4 g, 20.6 mmol, 1.2 eq.). The resulting mixture is stirred at rt for 4 hr. The organic solvent is evaporated under reduced pressure, and the ... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1.c1ccc2ccccc2c1 | Other | C1CCOC1 | null | 4 | CCn1c(-c2cccc3ccccc23)nc(F)c1[Si](C)(C)C>C1CCOC1>CCn1cc(F)nc1-c1cccc2ccccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-3f58c3e8254649fcb1cc5fa9783b5209 | CC#N.CCOC(=O)C(=O)C(C)=O.NCc1cccc2ccccc12>>CCOC(=O)c1[nH]c(-c2cccc3ccccc23)nc1C | C(C)OC(C(C(C)=O)=O)=O.C1(=CC=CC2=CC=CC=C12)CN.C(C)#N>>C(C)OC(=O)C=1NC(=NC1C)C1=CC=CC2=CC=CC=C12 | CC#[N:19].O=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:20](=O)[CH3:21].[NH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[nH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[n:19][c:20]1[CH3:21] | CC#N.CCOC(=O)C(=O)C(C)=O.NCc1cccc2ccccc12 | CCOC(=O)c1[nH]c(-c2cccc3ccccc23)nc1C | null | null | null | Aromatic Heterocycle Formation | OtherReaction | aa158c8d7e0a34e08a94bd0c9bf6ae44273956195bd167763fe3fbf92c70be90 | 3ac027b3c2941a6ffc7e285e96b5051b88c786e5ee70393eaeeba59628125919 | c1ccc2c(-c3ncc[nH]3)cccc2c1 | C-C#[N;H0;D1;+0:1].O=[C;H0;D3;+0:2](-[C;D1;H3:3])-[C;H0;D3;+0:4](=O)-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8].[NH2;D1;+0:9]-[CH2;D2;+0:10]-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](:[c:15]):[c:16]>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:4]1:[nH;D2;+0:9]:[c;H0;D3;+0:10](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](:[c:15]):[c:16]... | null | [] | null | null | null | null | A solution of 2,3-dioxobutyric acid ethyl ester, (Z)-2-oxime (3 g), 1-naphthalenemethylamine (3.26 g) in acetonitrile (45 ml) is refluxed for 10 hr to give a white precipitate. The solid is then collected, washed with acetonitrile and dried to yield 5-methyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid ethyl ester.... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ester.Nitrile.Primary amine | Ester | null | c1c[nH]cn1 | c1c[nH]cn1.c1ccc2ccccc2c1 | HO- | null | null | null | CC#N.CCOC(=O)C(=O)C(C)=O.NCc1cccc2ccccc12>>CCOC(=O)c1[nH]c(-c2cccc3ccccc23)nc1C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-3f60c457229c49a889b0212e15c53cb0 | CCOC(=O)c1[nH]c(-c2cccc3ccccc23)nc1C>>Cc1nc(-c2cccc3ccccc23)[nH]c1CO | C(C)OC(=O)C=1NC(=NC1C)C1=CC=CC2=CC=CC=C12.CC(C)C[AlH]CC(C)C>>CC1=C(NC(=N1)C1=CC=CC2=CC=CC=C12)CO | CCO[C:17]([c:16]1[c:2]([CH3:1])[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[nH:15]1)=[O:18]>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[nH:15][c:16]1[CH2:17][OH:18] | CCOC(=O)c1[nH]c(-c2cccc3ccccc23)nc1C | Cc1nc(-c2cccc3ccccc23)[nH]c1CO | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc2c(-c3ncc[nH]3)cccc2c1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[C;D1;H3:8]>>[C;D1;H3:8]-[c:7]1:[#7;a:6]:[c:5]:[#7;a:4]:[c:3]:1-[CH2;D2;+0:1]-[OH;D1;+0:2] | null | [] | null | null | 2 | HOUR | To a solution of 5-methyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid ethyl ester (280 mg) in THF (8 ml) is added DIBAL-H (3.3 ml, 1.5 M in toluene) at 0° C. The resulting solution is stirred at rt for 2 hr, and quenched with brine. The THF layer is separated and then evaporated. The residue is dissolved in EtOAc,... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1c[nH]cn1.c1ccc2ccccc2c1 | HO- | C1CCOC1 | null | 2 | CCOC(=O)c1[nH]c(-c2cccc3ccccc23)nc1C>C1CCOC1>Cc1nc(-c2cccc3ccccc23)[nH]c1CO |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ac11358a2b184d57b7b7919456a8a1dc | C1CCC(N2CCNCC2)C1.Cc1nc(-c2cccc3ccccc23)[nH]c1CO>>Cc1nc(-c2cccc3ccccc23)[nH]c1CN1CCN(C2CCCC2)CC1 | CCN(CC)CC.CC1=C(NC(=N1)C1=CC=CC2=CC=CC=C12)CO.O=S(Cl)Cl.C1(CCCC1)N1CCNCC1>>C1(CCCC1)N1CCN(CC1)CC=1NC(=NC1C)C1=CC=CC2=CC=CC=C12 | [NH:18]1[CH2:19][CH2:20][N:21]([CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)[CH2:27][CH2:28]1.O[CH2:17][c:16]1[c:2]([CH3:1])[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[nH:15]1>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[nH:15][c:16]1[CH2... | C1CCC(N2CCNCC2)C1.Cc1nc(-c2cccc3ccccc23)[nH]c1CO | Cc1nc(-c2cccc3ccccc23)[nH]c1CN1CCN(C2CCCC2)CC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | OtherReaction | 9885b3f1c049b08208f7467939360b5e493f0f916b8555f394ab4272f7b37bd7 | 87693a475e46c41583976158ec46dcaf8be8cc05c5635654a6a68033770f8d5c | c1ccc2c(-c3ncc(CN4CCN(C5CCCC5)CC4)[nH]3)cccc2c1 | O-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:1-[C;D1;H3:7].[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[C;D1;H3:7]-[c:6]1:[#7;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[N;H0;D3;+0:11]1-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-1 | null | [] | null | null | null | null | (5-Methyl-2-naphthalen-1-yl-3H-imidazol-4-yl)-methanol (40 mg) is treated with SOCl2, followed by N-cyclopentylpiperazine (60 mg) and Et3N (0.04 ml) in CH2Cl2 (2 ml). The crude is purified by column (2% Et3N, 3% MeOH in EtOAc) to afford the title compound as a white solid. LCMS 375.5 (M+1).
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1c[nH]cn1.c1ccc2ccccc2c1.C1C[NH]CC[NH]1.C1CCCC1 | HO- | C(Cl)Cl | null | null | C1CCC(N2CCNCC2)C1.Cc1nc(-c2cccc3ccccc23)[nH]c1CO>C(Cl)Cl>Cc1nc(-c2cccc3ccccc23)[nH]c1CN1CCN(C2CCCC2)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6865d417dc3a4acbabe299198449a15e | CCI.CCOC(=O)c1[nH]c(-c2cccc3ccccc23)nc1C.O>>CCOC(=O)c1c(C)nc(-c2cccc3ccccc23)n1CC.CCOC(=O)c1nc(-c2cccc3ccccc23)n(CC)c1C | C(C)I.C(C)OC(=O)C=1NC(=NC1C)C1=CC=CC2=CC=CC=C12.[H-].[Na+].O>>C(C)OC(=O)C=1N(C(=NC1C)C1=CC=CC2=CC=CC=C12)CC.C(C)OC(=O)C=1N=C(N(C1C)CC)C1=CC=CC2=CC=CC=C12 | I[CH2:22][CH3:23].[CH3:1][CH2:25][O:26][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)[nH:21]1.[OH2:3]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]([CH3:8])[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)[n:21]1[... | CCI.CCOC(=O)c1[nH]c(-c2cccc3ccccc23)nc1C.O | CCOC(=O)c1c(C)nc(-c2cccc3ccccc23)n1CC.CCOC(=O)c1nc(-c2cccc3ccccc23)n(CC)c1C | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | fc841b26e548053e0d0e23943f09005afbfa63cd82f2972d15d4541f514a0f9c | e4b1221eb59b6018d91e0913178985938131414a8c03bce5dfcc4f56490914f5 | c1ccc2c(-c3ncc[nH]3)cccc2c1.c1ccc2c(-c3ncc[nH]3)cccc2c1 | I-[CH2;D2;+0:1]-[C;D1;H3:2].[C;D1;H3:3]-[c:4]1:[#7;a:5]:[c:6](-[c:7]):[nH;D2;+0:8]:[c:9]:1-[C;H0;D3;+0:10](=[O;D1;H0:11])-[O;H0;D2;+0:12]-[CH2;D2;+0:13]-[CH3;D1;+0:14].[OH2;D0;+0:15]>>[C;D1;H3:16]-[CH2;D2;+0:13]-[O;H0;D2;+0:12]-[C:17](=[O;D1;H0:18])-[c:19].[C;D1;H3:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:8]1:[c:6](-[c:7]):[#7;a:5... | null | [] | 0 | CELSIUS | 30 | MINUTE | To a solution of 5-methyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid ethyl ester (1.5 g) in DMF (30 ml) is added NaH (320 mg, 60%) at rt. The solution is stirred for 30 min, and EtI (0.6 ml) is added. After 30 min, the mixture is cooled to 0° C. and H2O is added. The mixture is then extracted with EtOAc. The extr... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Ester.Ester | c1c[nH]cn1 | c1c[nH]cn1.c1c[nH]cn1.c1ccc2ccccc2c1 | c1c[nH]cn1.c1ccc2ccccc2c1.c1c[nH]cn1.c1ccc2ccccc2c1 | I- | CN(C)C=O | 0 | 0.5 | CCI.CCOC(=O)c1[nH]c(-c2cccc3ccccc23)nc1C.O>CN(C)C=O>CCOC(=O)c1c(C)nc(-c2cccc3ccccc23)n1CC.CCOC(=O)c1nc(-c2cccc3ccccc23)n(CC)c1C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-80481d022c79468f9dd37c5cace1fcb4 | CCn1c(-c2cccc3ccccc23)nc(C)c1C(=O)N1CCN(C2CCC2)CC1>>CCn1c(-c2cccc3ccccc23)nc(C)c1CN1CCN(C2CCC2)CC1 | C1(CCC1)N1CCN(CC1)C(=O)C=1N(C(=NC1C)C1=CC=CC2=CC=CC=C12)CC.CC(C)C[AlH]CC(C)C>>C1(CCC1)N1CCN(CC1)CC=1N(C(=NC1C)C1=CC=CC2=CC=CC=C12)CC | O=[C:19]([c:18]1[n:3]([CH2:2][CH3:1])[c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[n:15][c:16]1[CH3:17])[N:20]1[CH2:21][CH2:22][N:23]([CH:24]2[CH2:25][CH2:26][CH2:27]2)[CH2:28][CH2:29]1>>[CH3:1][CH2:2][n:3]1[c:4](-[c:5]2[cH:6][cH:7][cH:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]23)[n:15][c:1... | CCn1c(-c2cccc3ccccc23)nc(C)c1C(=O)N1CCN(C2CCC2)CC1 | CCn1c(-c2cccc3ccccc23)nc(C)c1CN1CCN(C2CCC2)CC1 | null | null | C1CCOC1 | Reduction | Reduction of tertiary amides to amines | f74c5a050b269ec4da3871c266f01344b7447381f47cda744f8b1e9c225ae62d | c8f3c617792f7a4fae96b8a97dc0ce23461ab85d8a738fe6caacff776ef51ffa | c1ccc2c(-c3ncc(CN4CCN(C5CCC5)CC4)[nH]3)cccc2c1 | O=[C;H0;D3;+0:1](-[#7:2](-[C:3])-[C:4])-[c:5]1:[#7;a:6](-[C:7]):[c:8]:[#7;a:9]:[c:10]:1-[C;D1;H3:11]>>[C:3]-[#7:2](-[CH2;D2;+0:1]-[c:5]1:[#7;a:6](-[C:7]):[c:8]:[#7;a:9]:[c:10]:1-[C;D1;H3:11])-[C:4] | null | [] | null | null | 2 | HOUR | To a solution of (4-cyclobutyl-piperazin-1-yl)-(3-ethyl-5-methyl-2-naphthalen-1-yl-3H-imidazol-4-yl)-methanone (40 mg) in THF (1 ml) is added DIBAL-H (0.25 ml, 1.5 M in toluene) at 0° C. The resulting solution is stirred at rt for 2 hr, and then quenched with brine. The THF layer is separated, evaporated and purified b... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | null | null | null | c1c[nH]cn1.c1ccc2ccccc2c1.C1C[NH]CC[NH]1.C1CCC1 | Other | C1CCOC1 | null | 2 | CCn1c(-c2cccc3ccccc23)nc(C)c1C(=O)N1CCN(C2CCC2)CC1>C1CCOC1>CCn1c(-c2cccc3ccccc23)nc(C)c1CN1CCN(C2CCC2)CC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-49b7772e7ec2441798f0cd7657c64a6c | CCn1cc(C(O)C2CCNCC2)nc1-c1cccc2ccccc12.O=C1CCC1>>CCn1cc(C(O)C2CCN(C3CCC3)CC2)nc1-c1cccc2ccccc12 | C(C)(=O)O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].C(C)N1C(=NC(=C1)C(O)C1CCNCC1)C1=CC=CC2=CC=CC=C12.C1(CCC1)=O>>C1(CCC1)N1CCC(CC1)C(O)C=1N=C(N(C1)CC)C1=CC=CC2=CC=CC=C12 | [CH3:1][CH2:2][n:3]1[cH:4][c:5]([CH:6]([OH:7])[CH:8]2[CH2:9][CH2:10][NH:11][CH2:16][CH2:17]2)[n:18][c:19]1-[c:20]1[cH:21][cH:22][cH:23][c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]12.O=[C:12]1[CH2:13][CH2:14][CH2:15]1>>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([CH:6]([OH:7])[CH:8]2[CH2:9][CH2:10][N:11]([CH:12]3[CH2:13][CH2:14][CH2:1... | CCn1cc(C(O)C2CCNCC2)nc1-c1cccc2ccccc12.O=C1CCC1 | CCn1cc(C(O)C2CCN(C3CCC3)CC2)nc1-c1cccc2ccccc12 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | reductive amination | 4beccb96faa28d88380728f020be13ff3debe8152a8220a924c88cfbe909e1b6 | 99acf13bfcfe579f51ccb82c65e4ca039ee7ca9b6fcd2747a3d9a292a88e564e | c1ccc2c(-c3nc(CC4CCN(C5CCC5)CC4)c[nH]3)cccc2c1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-1.[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-1)-[C:8]-[C:9] | null | [] | null | null | 8 | HOUR | To a solution of (1-ethyl-2-naphthalen-1-yl-1H-imidazol-4-yl)-piperidin-4-yl-methanol (0.53 g) in CH2ClCH2Cl (12 ml) is added cyclobutanone (0.95 ml), followed by NaBH(OAc)3 and acetic acid (0.1 ml). The resulting mixture is stirred at rt overnight, diluted with CH2Cl2, washed with Na2CO3 (1M), H2O and brine, dried and... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Secondary amine | Tertiary amine | C1CCNCC1.C1CCC1 | C1CC[NH]CC1.C1CCC1 | c1c[nH]cn1.C1CC[NH]CC1.C1CCC1.c1ccc2ccccc2c1 | Other | C(Cl)Cl | null | 8 | CCn1cc(C(O)C2CCNCC2)nc1-c1cccc2ccccc12.O=C1CCC1>C(Cl)Cl>CCn1cc(C(O)C2CCN(C3CCC3)CC2)nc1-c1cccc2ccccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-996368e539504cb7806c1a8a3ac7055d | CCn1cc(C(O)C2CCN(C3CCC3)CC2)nc1-c1cccc2ccccc12.CI>>CCn1cc(C(OC)C2CCN(C3CCC3)CC2)nc1-c1cccc2ccccc12 | CI.C1(CCC1)N1CCC(CC1)C(O)C=1N=C(N(C1)CC)C1=CC=CC2=CC=CC=C12.[H-].[Na+]>>C1(CCC1)N1CCC(CC1)C(OC)C=1N=C(N(C1)CC)C1=CC=CC2=CC=CC=C12 | [CH3:1][CH2:2][n:3]1[cH:4][c:5]([CH:6]([OH:7])[CH:9]2[CH2:10][CH2:11][N:12]([CH:13]3[CH2:14][CH2:15][CH2:16]3)[CH2:17][CH2:18]2)[n:19][c:20]1-[c:21]1[cH:22][cH:23][cH:24][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]12.I[CH3:8]>>[CH3:1][CH2:2][n:3]1[cH:4][c:5]([CH:6]([O:7][CH3:8])[CH:9]2[CH2:10][CH2:11][N:12]([CH:13]3[CH2:1... | CCn1cc(C(O)C2CCN(C3CCC3)CC2)nc1-c1cccc2ccccc12.CI | CCn1cc(C(OC)C2CCN(C3CCC3)CC2)nc1-c1cccc2ccccc12 | null | null | CCOC(=O)C.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 31ec8f945a35f4f87287620e27b68692ce42732551035fbac056df61d9acce14 | 08f7221cae607d413f579138dcaa6997bebcad2bbb42d2f1b3b2a2d886befb37 | c1ccc2c(-c3nc(CC4CCN(C5CCC5)CC4)c[nH]3)cccc2c1 | I-[CH3;D1;+0:1].[#7;a:2]:[c:3](-[C:4](-[C:5])-[OH;D1;+0:6]):[c:7]:[#7;a:8]>>[#7;a:2]:[c:3](-[C:4](-[C:5])-[O;H0;D2;+0:6]-[CH3;D1;+0:1]):[c:7]:[#7;a:8] | null | [] | null | null | 30 | MINUTE | To a solution of (1-cyclobutyl-piperidin-4-yl)-(1-ethyl-2-naphthalen-1-yl-1H-imidazol-4-yl)-methanol (20 mg) in DMF (2 ml) is added NaH (6 mg, 60%), followed by CH3I (15 mg). The resulting mixture is stirred at rt for 30 min, and then diluted with EtOAc, washed with water and brine, dried and solvent removed. The crude... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ether | null | null | c1c[nH]cn1.C1CC[NH]CC1.C1CCC1.c1ccc2ccccc2c1 | HI | CCOC(=O)C.CN(C)C=O | null | 0.5 | CCn1cc(C(O)C2CCN(C3CCC3)CC2)nc1-c1cccc2ccccc12.CI>CCOC(=O)C.CN(C)C=O>CCn1cc(C(OC)C2CCN(C3CCC3)CC2)nc1-c1cccc2ccccc12 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-70c666ce7b4a4ede94971688eaf95325 | CCI.N#CCC#N>>CCC(C#N)(C#N)CC | CC(C)(C)[O-].[K+].C(CC#N)#N.C(C)I>>C(C)C(C#N)(C#N)CC | I[CH2:2][CH3:1].[CH2:3]([C:4]#[N:5])[C:8]#[N:7]>>[CH3:1][CH2:2][C:3]([C:4]#[N:5])([C:6]#[N:7])[CH2:8][CH3:9] | CCI.N#CCC#N | CCC(C#N)(C#N)CC | null | CCCC[N+](CCCC)(CCCC)CCCC.[Br-] | null | C-C Coupling | OtherReaction | beef5228fcaf3ca6d461603efc4c90a139b5ff1639f3130cb134016aa21deb02 | cfd1a6601301109b513394252983fd8657e1a8ade5f928a44f205d21f84af183 | null | I-[CH2;D2;+0:1]-[C;D1;H3:2].[N;D1;H0:3]#[C:4]-[CH2;D2;+0:5]-[C;H0;D2;+0:6]#[N;H0;D1;+0:7]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[C;H0;D4;+0:5](-[C:4]#[N;D1;H0:3])(-[C:8]#[N;H0;D1;+0:7])-[CH2;D2;+0:6]-[C;D1;H3:9] | null | [] | null | null | 30 | MINUTE | Malononitrile (15.2 g) was mixed with TBAB (3.0 g, 4 mol %) and ethyl iodide (36.8 mL, 2 equiv.). After stirring for 30 minutes at room temperature, the mixture was cooled in an ice bath, KOtBu (51.6 g, 2 equiv.) was added portionwise, the ice bath was removed, and the mixture was stirred for 30 minutes at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Nitrile | Nitrile | null | null | null | I- | CCCC[N+](CCCC)(CCCC)CCCC.[Br-] | null | 0.5 | CCI.N#CCC#N>CCCC[N+](CCCC)(CCCC)CCCC.[Br-]>CCC(C#N)(C#N)CC |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0f8d79ba1d9c4f4d8cc4deb72e397bf0 | CCC(C#N)(C#N)CC>>CCC(CC)(CN)CN | [H-].[H-].[H-].[H-].[Li+].[Al+3].C(C)C(C#N)(C#N)CC>>C(C)C(CN)(CN)CC | [CH3:1][CH2:2][C:3]([CH2:4][CH3:5])([C:6]#[N:7])[C:8]#[N:9]>>[CH3:1][CH2:2][C:3]([CH2:4][CH3:5])([CH2:6][NH2:7])[CH2:8][NH2:9] | CCC(C#N)(C#N)CC | CCC(CC)(CN)CN | null | null | CCOCC | Reduction | OtherReaction | c2340da2c258bf397d4a8fa28e5be42ecf34d1d4e5e541c0aa9e06499bdba3ed | cb8a07357b502aa07f8272954f5a9149eabfa75b76e8c8c18ad60272c8d4f167 | null | [C:1]-[C:2](-[C:3])(-[C;H0;D2;+0:4]#[N;H0;D1;+0:5])-[C;H0;D2;+0:6]#[N;H0;D1;+0:7]>>[C:1]-[C:2](-[C:3])(-[CH2;D2;+0:4]-[NH2;D1;+0:5])-[CH2;D2;+0:6]-[NH2;D1;+0:7] | null | [] | null | null | 8 | HOUR | A suspension of LiAlH4 (4.66 g) in dry Et2O (100 mL) was cooled in an ice bath, and a solution of 2,2-diethyl-malononitrile (5.0 g) in Et2O (50 mL) was added dropwise at such a rate that the temperature was kept below 20° C. The mixture was stirred overnight at room temperature, cooled in an ice bath, and quenched by a... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Nitrile | Primary amine.Primary amine | null | null | null | null | CCOCC | null | 8 | CCC(C#N)(C#N)CC>CCOCC>CCC(CC)(CN)CN |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e38ddba0bf6b4ab48ea0622ffafd9638 | CCC(CC)(CN)CN>>CCC1(CC)CN=NC1 | C(C)C(CN)(CN)CC.OO.[O-]Cl.[Na+]>>C(C)C1(CN=NC1)CC | [CH3:1][CH2:2][C:3]([CH2:4][CH3:5])([CH2:6][NH2:7])[CH2:9][NH2:8]>>[CH3:1][CH2:2][C:3]1([CH2:4][CH3:5])[CH2:6][N:7]=[N:8][CH2:9]1 | CCC(CC)(CN)CN | CCC1(CC)CN=NC1 | null | null | CO.O | Oxidation | OtherReaction | da36b35276a0176b37cc03b309f4fbef7c307ef1eae406084866f9301abaa71c | ccb08cdd906ab1c43b965b3f381a9df42e8b4b6ec4217dac787b89befda7069c | C1CN=NC1 | [NH2;D1;+0:1]-[C:2]-[C:3]-[C:4]-[NH2;D1;+0:5]>>[C:3]1-[C:2]-[N;H0;D2;+0:1]=[N;H0;D2;+0:5]-[C:4]-1 | 77 | [{"value": 77.0, "product": "C(C)C1(CN=NC1)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 2,2-Diethyl-propane-1,3-diamine (5.0 g) was taken up in a mixture of H2O (40 mL) and MeOH (10 mL), and cooled in an ice bath. Simultaneously, H2O2 (24.2 mL of a 30% solution, 6 equiv.) and NaClO (54.9 mL of a 10% solution, 2.4 equiv.) were added dropwise, the ice bath was removed, and the mixture was stirred for 2 h. a... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Diazene | null | C1CN=NC1 | C1CN=NC1 | null | CO.O | null | 2 | CCC(CC)(CN)CN>CO.O>CCC1(CC)CN=NC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-00f2e267ad9c482b927013f0e68e637b | BrCCCCBr.N#CCC#N>>N#CC1(C#N)CCCC1 | C(CC#N)#N.C1CCC2=NCCCN2CC1.BrCCCCBr>>C1(CCCC1)(C#N)C#N | Br[CH2:6][CH2:7][CH2:8][CH2:9]Br.[N:1]#[C:2][CH2:3][C:4]#[N:5]>>[N:1]#[C:2][C:3]1([C:4]#[N:5])[CH2:6][CH2:7][CH2:8][CH2:9]1 | BrCCCCBr.N#CCC#N | N#CC1(C#N)CCCC1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 90ff2cdd2efc3b7e3d5fddf28ea72ab16385a91dc99fbace2077f543bebdb44a | 7b68950fc1047c59bb49c25e850f5a51cbe91a99bb87839c4547aec123110e4b | C1CCCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-Br.[N;D1;H0:5]#[C:6]-[CH2;D2;+0:7]-[C:8]#[N;D1;H0:9]>>[N;D1;H0:5]#[C:6]-[C;H0;D4;+0:7]1(-[C:8]#[N;D1;H0:9])-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-1 | null | [] | 80 | CELSIUS | 2 | HOUR | Malononitrile (15.0 g) was dissolved in dry DMF (200 mL) and cooled in an ice bath. Subsequently, DBU (75 mL, 2.2. equiv.) and 1,4-dibromobutane (29.6 mL, 1.1 equiv.) were added dropwise. The ice bath was removed, an extra 100 mL of dry DMF was added, and the mixture was stirred at 80° C. for 2 h. After cooling to ambi... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | null | C1CCCC1 | C1CCCC1 | HBr | CN(C)C=O | 80 | 2 | BrCCCCBr.N#CCC#N>CN(C)C=O>N#CC1(C#N)CCCC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1fe459bff36d43cdb7b880e57236a9c8 | N#CC1(C#N)CCCC1>>NCC1(CN)CCCC1 | [H-].[H-].[H-].[H-].[Li+].[Al+3].C1(CCCC1)(C#N)C#N>>NCC1(CCCC1)CN | [N:1]#[C:2][C:3]1([C:4]#[N:5])[CH2:6][CH2:7][CH2:8][CH2:9]1>>[NH2:1][CH2:2][C:3]1([CH2:4][NH2:5])[CH2:6][CH2:7][CH2:8][CH2:9]1 | N#CC1(C#N)CCCC1 | NCC1(CN)CCCC1 | null | null | CCOCC | Reduction | OtherReaction | c2340da2c258bf397d4a8fa28e5be42ecf34d1d4e5e541c0aa9e06499bdba3ed | cb8a07357b502aa07f8272954f5a9149eabfa75b76e8c8c18ad60272c8d4f167 | C1CCCC1 | [C:1]-[C:2](-[C;H0;D2;+0:3]#[N;H0;D1;+0:4])(-[C;H0;D2;+0:5]#[N;H0;D1;+0:6])-[C:7]>>[C:1]-[C:2](-[CH2;D2;+0:3]-[NH2;D1;+0:4])(-[CH2;D2;+0:5]-[NH2;D1;+0:6])-[C:7] | null | [] | null | null | 8 | HOUR | A suspension of LiAlH4 (4.74 g) in dry Et2O (100 mL) was cooled in an ice bath, and a solution of cyclopentane-1,1-dicarbonitrile (5.0 g) in Et2O (50 mL) was added dropwise at such a rate that the temperature was kept below 20° C. The mixture was stirred overnight at room temperature, cooled in an ice bath, and quenche... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Nitrile | Primary amine.Primary amine | null | null | C1CCCC1 | null | CCOCC | null | 8 | N#CC1(C#N)CCCC1>CCOCC>NCC1(CN)CCCC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-950943709ef94e2cbd449c048cfa7060 | NCC1(CN)CCCC1>>C1CCC2(C1)CN=NC2 | NCC1(CCCC1)CN.OO.[O-]Cl.[Na+]>>C1N=NCC12CCCC2 | [CH2:1]1[CH2:2][CH2:3][C:4]([CH2:6][NH2:7])([CH2:9][NH2:8])[CH2:5]1>>[CH2:1]1[CH2:2][CH2:3][C:4]2([CH2:5]1)[CH2:6][N:7]=[N:8][CH2:9]2 | NCC1(CN)CCCC1 | C1CCC2(C1)CN=NC2 | null | null | CO.O | Oxidation | OtherReaction | 090d5d4e81b866fa7ef181e233ee2a58f5345ea9d72b6baa3e51989a1d603bf5 | ccb08cdd906ab1c43b965b3f381a9df42e8b4b6ec4217dac787b89befda7069c | C1CCC2(C1)CN=NC2 | [NH2;D1;+0:1]-[C:2]-[C:3]-[C:4]-[NH2;D1;+0:5]>>[C:3]1-[C:2]-[N;H0;D2;+0:1]=[N;H0;D2;+0:5]-[C:4]-1 | 90 | [{"value": 90.0, "product": "C1N=NCC12CCCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | C-(1-Aminomethyl-cyclopentyl)-methylamine (4.87 g) was taken up in a mixture of H2O (40 mL) and MeOH (10 mL), and cooled in an ice bath. Simultaneously, H2O2 (23.9 mL of a 30% solution. 6 equiv.) and NaClO (54.3 mL of a 10% solution, 2.4 equiv.) were added dropwise, the ice bath was removed, and the mixture was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Diazene | null | C1CCC2(C1)CN=NC2 | C1CCC2(C1)CN=NC2 | null | CO.O | null | 2 | NCC1(CN)CCCC1>CO.O>C1CCC2(C1)CN=NC2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0f24ae48faae41c7bd08e7d80696285f | BrCCCCCBr.N#CCC#N>>N#CC1(C#N)CCCCC1 | C(CC#N)#N.C1CCC2=NCCCN2CC1.BrCCCCCBr>>C1(CCCCC1)(C#N)C#N | Br[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]Br.[N:1]#[C:2][CH2:3][C:4]#[N:5]>>[N:1]#[C:2][C:3]1([C:4]#[N:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1 | BrCCCCCBr.N#CCC#N | N#CC1(C#N)CCCCC1 | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 82c068fef1b7bbb44db21c6f07dae9191b2260270bca592e94309bb776f329ef | 7b68950fc1047c59bb49c25e850f5a51cbe91a99bb87839c4547aec123110e4b | C1CCCCC1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-Br.[N;D1;H0:6]#[C:7]-[CH2;D2;+0:8]-[C:9]#[N;D1;H0:10]>>[N;D1;H0:6]#[C:7]-[C;H0;D4;+0:8]1(-[C:9]#[N;D1;H0:10])-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1 | null | [] | 80 | CELSIUS | 2 | HOUR | Malononitril (15.0 g) was dissolved in dry DMF (200 mL). Subsequently, DBU (75 mL) and 1,5-dibromopentane (34 mL) were added at 0° C. (ice bath). The ice bath was removed and the reaction was stirred for 2 h at 80° C. After cooling down, the reaction was poured into DCM. The organic layer was washed several times with ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | null | C1CCCCC1 | C1CCCCC1 | HBr | CN(C)C=O | 80 | 2 | BrCCCCCBr.N#CCC#N>CN(C)C=O>N#CC1(C#N)CCCCC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fb00120b424c46bd9458335a138b45b6 | N#CC1(C#N)CCCCC1>>NCC1(CN)CCCCC1 | C1(CCCCC1)(C#N)C#N.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>NCC1(CCCCC1)CN | [N:1]#[C:2][C:3]1([C:4]#[N:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1>>[NH2:1][CH2:2][C:3]1([CH2:4][NH2:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1 | N#CC1(C#N)CCCCC1 | NCC1(CN)CCCCC1 | null | null | CCOCC | Reduction | OtherReaction | c2340da2c258bf397d4a8fa28e5be42ecf34d1d4e5e541c0aa9e06499bdba3ed | cb8a07357b502aa07f8272954f5a9149eabfa75b76e8c8c18ad60272c8d4f167 | C1CCCCC1 | [C:1]-[C:2](-[C;H0;D2;+0:3]#[N;H0;D1;+0:4])(-[C;H0;D2;+0:5]#[N;H0;D1;+0:6])-[C:7]>>[C:1]-[C:2](-[CH2;D2;+0:3]-[NH2;D1;+0:4])(-[CH2;D2;+0:5]-[NH2;D1;+0:6])-[C:7] | null | [] | null | null | 8 | HOUR | Cyclohexane-1,1-dicarbonitrile (20.0 g) was taken up in dry Et2 (70 mL). This mixture was added dropwise to a suspension of LiAlH4 (17.0 g) in dry Et2O (250 mL) cooled in an ice bath. The mixture was stirred overnight at room temperature, cooled in an ice bath, and quenched by adding H2O (17.0 mL), 2M aqueous NaOH (34.... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Nitrile | Primary amine.Primary amine | null | null | C1CCCCC1 | null | CCOCC | null | 8 | N#CC1(C#N)CCCCC1>CCOCC>NCC1(CN)CCCCC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2504d08685a64c35a6ba654bf4472cd6 | NCC1(CN)CCCCC1>>C1CCC2(CC1)CN=NC2 | OO.[O-]Cl.[Na+].NCC1(CCCCC1)CN>>C1N=NCC12CCCCC2 | [CH2:1]1[CH2:2][CH2:3][C:4]([CH2:7][NH2:8])([CH2:10][NH2:9])[CH2:5][CH2:6]1>>[CH2:1]1[CH2:2][CH2:3][C:4]2([CH2:5][CH2:6]1)[CH2:7][N:8]=[N:9][CH2:10]2 | NCC1(CN)CCCCC1 | C1CCC2(CC1)CN=NC2 | null | null | CO.O | Oxidation | OtherReaction | bf22768aa26d28bfe83035a6aafeb24fa2abdfdb833ff6d3a436f3fafddf56f4 | ccb08cdd906ab1c43b965b3f381a9df42e8b4b6ec4217dac787b89befda7069c | C1CCC2(CC1)CN=NC2 | [NH2;D1;+0:1]-[C:2]-[C:3]-[C:4]-[NH2;D1;+0:5]>>[C:4]1-[C:3]-[C:2]-[N;H0;D2;+0:1]=[N;H0;D2;+0:5]-1 | null | [] | null | null | 45 | MINUTE | C-(1-Aminomethyl-cyclohexyl)-methylamine (10.0 g) was taken up in a mixture of H2O (40 mL) and MeOH (10 mL), and cooled in an ice bath. Simultaneously, H2O2 (44.3 mL of a 30% solution, 6 equiv.) and NaClO (125.5 mL of a 10% solution, 2.4 equiv.) were added dropwise, the ice bath was removed, and the mixture was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Diazene | null | C1CCC2(CC1)CN=NC2 | C1CCC2(CC1)CN=NC2 | null | CO.O | null | 0.75 | NCC1(CN)CCCCC1>CO.O>C1CCC2(CC1)CN=NC2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-65b3ead1483c4c8daf4f97d9b1eacd84 | CCC(C(C)=O)C(=O)OC.Cc1ccc(S(=O)(=O)O)cc1.OCCO>>CCOC(=O)C(CC)C1(C)OCCO1 | COC(C(C(=O)C)CC)=O.C(CO)O.CC=1C=CC(=CC1)S(=O)(=O)O.O>>C(C)OC(C(CC)C1(OCCO1)C)=O | [CH3:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH3:8])[C:9]([CH3:10])=[O:11].O=S(=O)(O)c1ccc([CH3:12])cc1.O[CH2:1][CH2:13][OH:14]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][CH3:8])[C:9]1([CH3:10])[O:11][CH2:12][CH2:13][O:14]1 | CCC(C(C)=O)C(=O)OC.Cc1ccc(S(=O)(=O)O)cc1.OCCO | CCOC(=O)C(CC)C1(C)OCCO1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | dd2b98d5fb6672d900f603c2b5596e2f1635a2b64362175d9917c11db3a04bbf | 0398a9978bf1c292fba63599c8a89120980e704d65726782f860fad6206da71f | C1COCO1 | O-S(=O)(=O)-c1:c:c:c(-[CH3;D1;+0:1]):c:c:1.O-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[OH;D1;+0:4].[C:5]-[C:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[CH3;D1;+0:10])-[C;H0;D3;+0:11](-[C;D1;H3:12])=[O;H0;D1;+0:13]>>[C:5]-[C:6](-[C:7](=[O;D1;H0:8])-[#8:9]-[CH2;D2;+0:10]-[CH3;D1;+0:2])-[C;H0;D4;+0:11]1(-[C;D1;H3:12])-[O;H0;D2;+0:13]-[CH2;D2;+0:1... | null | [] | null | null | null | null | Methyl-2-ethylacetoacetate (100 mL) was taken up in toluene (250 mL). Ethylene glycol (46.9 mL, 1.35 equiv.) and a catalytic amount of p-TsOH.H2O were added, and the mixture was refluxed overnight under Dean-Stark conditions. After cooling to ambient temperature, the mixture was washed with 5% aqueous NaHCO3 and satura... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Ketone.Ester.Primary alcohol.Primary alcohol | Ester.Ether.Ether | c1ccccc1 | C1COCO1 | C1COCO1 | TsOH.HO- | C1(=CC=CC=C1)C | null | null | CCC(C(C)=O)C(=O)OC.Cc1ccc(S(=O)(=O)O)cc1.OCCO>C1(=CC=CC=C1)C>CCOC(=O)C(CC)C1(C)OCCO1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-fcb3b7df7fec4410b638d2761073fb52 | CCOC(=O)C(CC)C1(C)OCCO1>>CCC(CO)C1(C)OCCO1 | C(C)OC(C(CC)C1(OCCO1)C)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>CC1(OCCO1)C(CO)CC | CCO[C:4]([CH:3]([CH2:2][CH3:1])[C:6]1([CH3:7])[O:8][CH2:9][CH2:10][O:11]1)=[O:5]>>[CH3:1][CH2:2][CH:3]([CH2:4][OH:5])[C:6]1([CH3:7])[O:8][CH2:9][CH2:10][O:11]1 | CCOC(=O)C(CC)C1(C)OCCO1 | CCC(CO)C1(C)OCCO1 | null | null | CCOCC | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1COCO1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[C:5](-[#8:6])-[#8:7]>>[#8:6]-[C:5](-[C:3](-[C:4])-[CH2;D2;+0:1]-[OH;D1;+0:2])-[#8:7] | null | [] | null | null | null | null | 2-(2-Methyl-[1,3]dioxolan-2-yl)-butyric acid ethyl ester (85.5 g) was taken up in dry Et2O (50 mL). This mixture was added dropwise to a suspension of LiAlH4 (16.1 g) in dry Et2O (200 mL), cooled in an ice bath. The mixture was refluxed for 4 h., cooled in an ice bath, and quenched by adding H2O (16.1 mL), 2M aqueous N... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1COCO1 | HO- | CCOCC | null | null | CCOC(=O)C(CC)C1(C)OCCO1>CCOCC>CCC(CO)C1(C)OCCO1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-59cd7a8427e64aa59ace39ad6c78da57 | CC(=O)OC(C)=O.CCC(CO)C(C)=O>>CCC(COC(C)=O)C(C)=O | C(=O)(O)[O-].[Na+].C(C)(=O)OC(C)=O.OCC(C(C)=O)CC.CO>>C(C)C(COC(C)=O)C(C)=O | CC(=O)O[C:6]([CH3:7])=[O:8].[CH3:1][CH2:2][CH:3]([CH2:4][OH:5])[C:9]([CH3:10])=[O:11]>>[CH3:1][CH2:2][CH:3]([CH2:4][O:5][C:6]([CH3:7])=[O:8])[C:9]([CH3:10])=[O:11] | CC(=O)OC(C)=O.CCC(CO)C(C)=O | CCC(COC(C)=O)C(C)=O | null | CN(C)C=1C=CN=CC1 | C(Cl)(Cl)Cl | Acylation | Transesterification | f81e513b7b512b10157c16426844efd8d88e34c97987c1347c6ba8a688351205 | fc27d67c790d5fb520ba5d49de1490661fa5b822b714863734ce7e3029dfa84f | null | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C;D1;H3:4]-[C:5](=[O;D1;H0:6])-[C:7]-[C:8]-[OH;D1;+0:9]>>[C;D1;H3:4]-[C:5](=[O;D1;H0:6])-[C:7]-[C:8]-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3] | null | [] | null | null | 8 | HOUR | 3-Hydroxymethyl-pentan-2-one (20.7 g) was dissolved in CHCl3 (150 mL) and cooled in an ice bath. Acetic anhydride (80 mL) was added, followed by DMAP (2.18 g), and the mixture was stirred overnight at room temperature. After cooling in an ice bath, MeOH (120 mL) was added dropwise, and the mixture was poured into a sat... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary alcohol | Ester | null | null | null | HO- | CN(C)C=1C=CN=CC1.C(Cl)(Cl)Cl | null | 8 | CC(=O)OC(C)=O.CCC(CO)C(C)=O>CN(C)C=1C=CN=CC1.C(Cl)(Cl)Cl>CCC(COC(C)=O)C(C)=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e0efabadef9048dc84919e5833e7dc29 | C=O.CNC.O=C1CCCCC1>>CN(C)CC1CCCCC1=O | C1(CCCCC1)=O.C=O.Cl.CNC>>CN(C)CC1C(CCCC1)=O | O=[CH2:4].[CH3:1][NH:2][CH3:3].[CH2:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1=[O:11]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1=[O:11] | C=O.CNC.O=C1CCCCC1 | CN(C)CC1CCCCC1=O | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 2bf1ede5572b12bbfdb633effec5cdb6469d6ff6fc98f249a248eade23e7c341 | e8784011446fecd0a9b69948eec8f6e670a0f5952d23e21c3e86b629168fc3f8 | O=C1CCCCC1 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[NH;D2;+0:3]-[C;D1;H3:4].[C:5]-[C:6]-[CH2;D2;+0:7]-[C:8](=[O;D1;H0:9])-[C:10]>>[C:5]-[C:6]-[CH;D3;+0:7](-[CH2;D2;+0:1]-[N;H0;D3;+0:3](-[C;D1;H3:2])-[C;D1;H3:4])-[C:8](=[O;D1;H0:9])-[C:10] | null | [] | null | null | null | null | To cyclohexanone (259 mL) was added formaldehyde (37.2 mL of a 37% aqueous solution) and dimethylamine hydrochloride (40.8 g). The stirred mixture was slowly heated and refluxed for 1 h. After cooling to ambient temperature H2O was added, and the mixture was extracted twice with Et2O. The aqueous layer was made basic b... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Ketone.Secondary amine | Ketone.Tertiary amine | C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | HO- | O | null | null | C=O.CNC.O=C1CCCCC1>O>CN(C)CC1CCCCC1=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d60c876a3fb140c791fbe1953581d169 | CN(C)CC1CCCCC1=O.NN>>C1CCC2CNN=C2C1 | O.NN.CN(C)CC1C(CCCC1)=O>>N=1NCC2CCCCC12 | C[N:6](C)[CH2:5][CH:4]1[CH2:3][CH2:2][CH2:1][CH2:9][C:8]1=O.N[NH2:7]>>[CH2:1]1[CH2:2][CH2:3][CH:4]2[CH2:5][NH:6][N:7]=[C:8]2[CH2:9]1 | CN(C)CC1CCCCC1=O.NN | C1CCC2CNN=C2C1 | null | null | CCCCO | Miscellaneous | OtherReaction | 4fad93a6df77a16da6173b64a227379a563c7e32954554cdd404e670cc39a17d | 2c24edd496ac562589e3c82864b175f91077835801e55e36f11445a79aa1b0d9 | C1CCC2CNN=C2C1 | C-[N;H0;D3;+0:1](-C)-[C:2]-[C:3](-[C:4])-[C;H0;D3;+0:5](=O)-[C:6]-[C:7].N-[NH2;D1;+0:8]>>[C:7]-[C:6]-[C;H0;D3;+0:5]1=[N;H0;D2;+0:8]-[NH;D2;+0:1]-[C:2]-[C:3]-1-[C:4] | null | [] | null | null | null | null | Hydrazine hydrate (28.0 mL) was dissolved in n-BuOH (200 mL) and cooled in an ice bath. A solution of 2-dimethylaminomethyl-cyclohexanone (64.0 g) in n-BuOH (50 mL) was added dropwise, the mixture was slowly warmed and refluxed for 20 hours. The solvent was evaporated under reduced pressure.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Tertiary amine | Hydrazone | C1CCCCC1 | C1CCC2CNN=C2C1 | C1CCC2CNN=C2C1 | HO- | CCCCO | null | null | CN(C)CC1CCCCC1=O.NN>CCCCO>C1CCC2CNN=C2C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-47839d9892c84994b6ebb315809c5146 | CC(=O)C(C)(C)CO.CS(=O)(=O)Cl>>CC(=O)C(C)(C)COS(C)(=O)=O | OCC(C(C)=O)(C)C.N1=CC=CC=C1.S(=O)(=O)(C)Cl>>CC(COS(=O)(=O)C)(C(C)=O)C | [CH3:1][C:2](=[O:3])[C:4]([CH3:5])([CH3:6])[CH2:7][OH:8].Cl[S:9]([CH3:10])(=[O:11])=[O:12]>>[CH3:1][C:2](=[O:3])[C:4]([CH3:5])([CH3:6])[CH2:7][O:8][S:9]([CH3:10])(=[O:11])=[O:12] | CC(=O)C(C)(C)CO.CS(=O)(=O)Cl | CC(=O)C(C)(C)COS(C)(=O)=O | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | null | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[C:8]-[C:9]-[OH;D1;+0:10]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[O;H0;D2;+0:10]-[C:9]-[C:8]-[C:6](-[C;D1;H3:5])=[O;D1;H0:7] | null | [] | null | null | 20 | HOUR | 23.7 g 4-Hydroxy-3,3-dimethyl-butan-2-one was dissolved in 150 mL DCM. 49.5 mL (3 eq) pyridine and 17.5 mL (1.1 eq) mesylchloride were added and the mixture was stirred at room temperature for 20 hours. The suspension was filtered and the filter cake was washed two times with DCM. The filtrate was washed with 1 M HCl a... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | null | HCl | C(Cl)Cl | null | 20 | CC(=O)C(C)(C)CO.CS(=O)(=O)Cl>C(Cl)Cl>CC(=O)C(C)(C)COS(C)(=O)=O |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-82bf5f4e932d4b81942421c22a32c6e8 | C=O.CC(=O)c1ccccc1.CNC>>CN(C)CCC(=O)c1ccccc1 | Cl.C(C)(=O)C1=CC=CC=C1.C=O.Cl.CNC>>Cl.CN(CCC(=O)C1=CC=CC=C1)C | O=[CH2:4].[CH3:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | C=O.CC(=O)c1ccccc1.CNC | CN(C)CCC(=O)c1ccccc1 | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | 4c2c90d9f645c3d0fa0215eb47d000c493e1508aed4accd3d32ce0636c4f4501 | e8784011446fecd0a9b69948eec8f6e670a0f5952d23e21c3e86b629168fc3f8 | c1ccccc1 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[NH;D2;+0:3]-[C;D1;H3:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[C;D1;H3:2]-[N;H0;D3;+0:3](-[C;D1;H3:4])-[CH2;D2;+0:1]-[CH2;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8] | null | [] | null | null | null | null | To a solution of 0.5 mL concentrated aqueous HCl in 40 mL EtOH, acetophenone (30.0 g), paraformaldehyde (10.0 g) and dimethylamine hydrochloride (26.5 g) were added and the mixture was refluxed for 3 h. The mixture was cooled to room temperature, and the precipitate was filtered, washed with acetone and dried in vacuo ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Ketone.Secondary amine | Ketone.Tertiary amine | null | null | c1ccccc1 | HO- | CCO | null | null | C=O.CC(=O)c1ccccc1.CNC>CCO>CN(C)CCC(=O)c1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-97522613bb9a4da1bcaf9856395657d5 | CN(C)CCC(=O)c1ccccc1.NN>>c1ccc(C2=NNCC2)cc1 | O.NN.[OH-].[Na+].Cl.CN(CCC(=O)C1=CC=CC=C1)C>>C1(=CC=CC=C1)C1=NNCC1 | CN(C)[CH2:8][CH2:9][C:5](=O)[c:4]1[cH:3][cH:2][cH:1][cH:11][cH:10]1.[NH2:6][NH2:7]>>[cH:1]1[cH:2][cH:3][c:4]([C:5]2=[N:6][NH:7][CH2:8][CH2:9]2)[cH:10][cH:11]1 | CN(C)CCC(=O)c1ccccc1.NN | c1ccc(C2=NNCC2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 8ce4f433f4e843e34bf7c68272fb771615f9a0c93eba0d07ae65479474febfb7 | 75fb5ba864750cb62e4f77513eb04a2b99d0d7a6124313633b89c3d41f574e87 | c1ccc(C2=NNCC2)cc1 | C-N(-C)-[CH2;D2;+0:1]-[C:2]-[C;H0;D3;+0:3](=O)-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[NH2;D1;+0:8]>>[c:5]:[c:4](-[C;H0;D3;+0:3]1=[N;H0;D2;+0:7]-[NH;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-1):[c:6] | null | [] | 50 | CELSIUS | null | null | Under N2 atmosphere, 3-dimethylamino-1-phenyl-propan-1-one hydrochloride (37.2 g) was dissolved in warm MeOH (75 mL), and slowly added to a solution of hydrazine hydrate (23 mL) and 50% aqueous NaOH (12 mL) in MeOH (30 mL) stirred at 50° C. The mixture was refluxed for 2 hours and evaporated under reduced pressure. Ice... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Tertiary amine | Hydrazone | null | C1=NNCC1 | c1ccccc1.C1=NNCC1 | HO- | CO | 50 | null | CN(C)CCC(=O)c1ccccc1.NN>CO>c1ccc(C2=NNCC2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d84e1cfa1e914306a388d7fad0ad38b1 | C=O.CC(=O)c1ccc(Cl)cc1.CNC>>CN(C)CCC(=O)c1ccc(Cl)cc1 | ClC1=CC=C(C=C1)C(C)=O.Cl.CNC.C=O.Cl>>Cl.ClC1=CC=C(C=C1)C(CCN(C)C)=O | O=[CH2:4].[CH3:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1.[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([Cl:12])[cH:13][cH:14]1 | C=O.CC(=O)c1ccc(Cl)cc1.CNC | CN(C)CCC(=O)c1ccc(Cl)cc1 | null | null | CCO.CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 4c2c90d9f645c3d0fa0215eb47d000c493e1508aed4accd3d32ce0636c4f4501 | e8784011446fecd0a9b69948eec8f6e670a0f5952d23e21c3e86b629168fc3f8 | c1ccccc1 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[NH;D2;+0:3]-[C;D1;H3:4].[CH3;D1;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[C;D1;H3:2]-[N;H0;D3;+0:3](-[C;D1;H3:4])-[CH2;D2;+0:1]-[CH2;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8] | 112 | [{"value": 112.0, "product": "Cl.ClC1=CC=C(C=C1)C(CCN(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | null | null | To EtOH (80 mL), p-chloroacetophenone (77.3 g, 0.50 mol), dimethylamine hydrochloride (52.7 g, 0.65 mol), paraformaldehyde (19.8 g, 0.66 mol) and concentrated aqueous HCl (1 mL) were added and the mixture was refluxed for 5 h. The mixture was cooled to 40° C., acetone (400 mL) was added, and under stirring the mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Ketone.Secondary amine | Ketone.Tertiary amine | null | null | c1ccccc1 | HO- | CCO.CC(=O)C | 40 | null | C=O.CC(=O)c1ccc(Cl)cc1.CNC>CCO.CC(=O)C>CN(C)CCC(=O)c1ccc(Cl)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-46422b9f44604933bc9aea30a17a0796 | CN(C)CCC(=O)c1ccc(Cl)cc1.NN>>Clc1ccc(C2=NNCC2)cc1 | O.NN.[OH-].[Na+].Cl.ClC1=CC=C(C=C1)C(CCN(C)C)=O>>ClC1=CC=C(C=C1)C1=NNCC1 | CN(C)[CH2:9][CH2:10][C:6](=O)[c:5]1[cH:4][cH:3][c:2]([Cl:1])[cH:12][cH:11]1.[NH2:7][NH2:8]>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([C:6]2=[N:7][NH:8][CH2:9][CH2:10]2)[cH:11][cH:12]1 | CN(C)CCC(=O)c1ccc(Cl)cc1.NN | Clc1ccc(C2=NNCC2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 8ce4f433f4e843e34bf7c68272fb771615f9a0c93eba0d07ae65479474febfb7 | 75fb5ba864750cb62e4f77513eb04a2b99d0d7a6124313633b89c3d41f574e87 | c1ccc(C2=NNCC2)cc1 | C-N(-C)-[CH2;D2;+0:1]-[C:2]-[C;H0;D3;+0:3](=O)-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[NH2;D1;+0:8]>>[c:5]:[c:4](-[C;H0;D3;+0:3]1=[N;H0;D2;+0:7]-[NH;D2;+0:8]-[CH2;D2;+0:1]-[C:2]-1):[c:6] | null | [] | 50 | CELSIUS | null | null | Under N2 atmosphere, 1-(4-chloro-phenyl)-3-dimethylamino-propan-1-one hydrochloride (37.2 g) was dissolved in warm MeOH (75 mL), and slowly added to a solution of hydrazine hydrate (23 mL) and 50% aqueous NaOH (12 mL) in MeOH (30 mL) stirred at 50° C. The mixture was refluxed for 2 hours, and evaporated under reduced p... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Tertiary amine | Hydrazone | null | C1=NNCC1 | c1ccccc1.C1=NNCC1 | HO- | CO | 50 | null | CN(C)CCC(=O)c1ccc(Cl)cc1.NN>CO>Clc1ccc(C2=NNCC2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-7f87a3c0d5dd43838f708ff5bd85a19e | C=O.CC(=O)Cc1ccccc1>>C=C(C(C)=O)c1ccccc1 | C1(=CC=CC=C1)CC(C)=O.C=O.N1CCCCC1.CC(=O)O>>C1(=CC=CC=C1)C(C(C)=O)=C | O=[CH2:1].[CH2:2]([C:3]([CH3:4])=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[CH2:1]=[C:2]([C:3]([CH3:4])=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1 | C=O.CC(=O)Cc1ccccc1 | C=C(C(C)=O)c1ccccc1 | null | null | CO | C-C Coupling | Aldol condensation | e018cde8d346e007217a7d623d56b481720581fd1c253a681b8af9a72d815368 | 78c3c8e8e07039066e4f5b32d7bb729f171f9f9ecd946fef585e1cde063a41ff | c1ccccc1 | O=[CH2;D1;+0:1].[C;D1;H3:2]-[C:3](=[O;D1;H0:4])-[CH2;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](=[CH2;D1;+0:1])-[c:6](:[c:7]):[c:8] | null | [] | 60 | CELSIUS | 3 | HOUR | 1-Phenyl-propan-2-one (40.8 g) was dissolved in 200 ml of MeOH. Formaline (37%) (79 mL), piperidine (4 ml) and HOAc (4 ml) where added and de reaction was stirred for 3 h at 60° C. The reaction mixture was evaporated to dryness under reduced pressure. The residue was taken up in diethyl ether, and extracted with water.... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Ketone | Ketone.Vinyl | null | null | c1ccccc1 | HO- | CO | 60 | 3 | C=O.CC(=O)Cc1ccccc1>CO>C=C(C(C)=O)c1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-cc69153d0baf4ca4ad6a0b45e3ed5cb5 | NN.O=CC=Cc1ccccc1>>C1=NNC(c2ccccc2)C1 | O.NN.C(C=CC1=CC=CC=C1)=O>>C1(=CC=CC=C1)C1CC=NN1 | [NH2:2][NH2:3].O=[CH:1][CH:11]=[CH:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[CH:1]1=[N:2][NH:3][CH:4]([c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[CH2:11]1 | NN.O=CC=Cc1ccccc1 | C1=NNC(c2ccccc2)C1 | null | null | CC(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | e6b0a90bdf5439b0bafd80ec758c59b627b7e6dc79c973ee1b2fae667e8d9d63 | c3cbc07b90655a7aa9777b584274a03a2ec0cff34c5b5edc214a16916fe29f1c | C1=NNC(c2ccccc2)C1 | O=[CH;D2;+0:1]-[CH;D2;+0:2]=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6].[NH2;D1;+0:7]-[NH2;D1;+0:8]>>[c:5]:[c:4](-[CH;D3;+0:3]1-[CH2;D2;+0:2]-[CH;D2;+0:1]=[N;H0;D2;+0:7]-[NH;D2;+0:8]-1):[c:6] | null | [] | null | null | null | null | Under N2 atmosphere, hydrazine hydrate (9.2 mL) was added to a solution of cinnamaldehyde (10.0 g) in t-BuOH (20 mL). The mixture was refluxed overnight, followed by concentration under reduced pressure. Water was added to the residue, and the aqueous phase was extracted twice with DCM. The combined organic layers were... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aldehyde | Hydrazone | null | C1=NNCC1 | C1=NNCC1.c1ccccc1 | HO- | CC(C)(C)O | null | null | NN.O=CC=Cc1ccccc1>CC(C)(C)O>C1=NNC(c2ccccc2)C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b2811bb47fe647e7a75ae671606e3709 | NN.O=CC=Cc1cccnc1>>C1=NNC(c2cccnc2)C1 | O.NN.N1=CC(=CC=C1)C=CC=O>>N=1NC(CC1)C=1C=NC=CC1 | [NH2:2][NH2:3].O=[CH:1][CH:11]=[CH:4][c:5]1[cH:6][cH:7][cH:8][n:9][cH:10]1>>[CH:1]1=[N:2][NH:3][CH:4]([c:5]2[cH:6][cH:7][cH:8][n:9][cH:10]2)[CH2:11]1 | NN.O=CC=Cc1cccnc1 | C1=NNC(c2cccnc2)C1 | null | null | CC(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | e6b0a90bdf5439b0bafd80ec758c59b627b7e6dc79c973ee1b2fae667e8d9d63 | c3cbc07b90655a7aa9777b584274a03a2ec0cff34c5b5edc214a16916fe29f1c | C1=NNC(c2cccnc2)C1 | O=[CH;D2;+0:1]-[CH;D2;+0:2]=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8].[NH2;D1;+0:9]-[NH2;D1;+0:10]>>[c:5]:[c:4](-[CH;D3;+0:3]1-[CH2;D2;+0:2]-[CH;D2;+0:1]=[N;H0;D2;+0:9]-[NH;D2;+0:10]-1):[c:6]:[#7;a:7]:[c:8] | null | [] | null | null | null | null | Under N2 atmosphere, hydrazine hydrate (3.65 mL, 2 equiv.) was added to a solution of 3-(3-pyridyl)acrolein (5.0 g) in t-BuOH (25 mL). The mixture was refluxed for 3 days, followed by evaporation under reduced pressure. The residue was taken up in DCM and washed with 5% aqueous NaHCO3. The organic phase was dried over ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aldehyde | Hydrazone | null | C1=NNCC1 | C1=NNCC1.c1ccncc1 | HO- | CC(C)(C)O | null | null | NN.O=CC=Cc1cccnc1>CC(C)(C)O>C1=NNC(c2cccnc2)C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a7d533dfc1c64b57a8781969f0672fcd | CC(C=O)=Cc1ccccc1.NN>>CC1C=NNC1c1ccccc1 | O.NN.C(C)OCC.CC(C=O)=CC1=CC=CC=C1>>CC1C=NNC1C1=CC=CC=C1 | O=[CH:3][C:2]([CH3:1])=[CH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1.[NH2:4][NH2:5]>>[CH3:1][CH:2]1[CH:3]=[N:4][NH:5][CH:6]1[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | CC(C=O)=Cc1ccccc1.NN | CC1C=NNC1c1ccccc1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | e6b0a90bdf5439b0bafd80ec758c59b627b7e6dc79c973ee1b2fae667e8d9d63 | c3cbc07b90655a7aa9777b584274a03a2ec0cff34c5b5edc214a16916fe29f1c | C1=NNC(c2ccccc2)C1 | O=[CH;D2;+0:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7].[NH2;D1;+0:8]-[NH2;D1;+0:9]>>[C;D1;H3:3]-[CH;D3;+0:2]1-[CH;D2;+0:1]=[N;H0;D2;+0:8]-[NH;D2;+0:9]-[CH;D3;+0:4]-1-[c:5](:[c:6]):[c:7] | null | [] | null | null | 8 | HOUR | 5.22 ml (1 equiv.) hydrazine hydrate was added to 100 mL diethylether. The emulsion was cooled with an ice bath. 15.0 mL 2-Methyl-3-phenyl-propenal was added dropwise, and the mixture was stirred overnight at room temperature. H2O was added, the organic layer was separated and the aqueous layer was extracted with dieth... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aldehyde | Hydrazone | null | C1=NNCC1 | C1=NNCC1.c1ccccc1 | HO- | O | null | 8 | CC(C=O)=Cc1ccccc1.NN>O>CC1C=NNC1c1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d24af1c2c83e4a5d85276af70c02367d | CCCC=O.O=Cc1ccccc1>>CCC(C=O)=Cc1ccccc1 | Cl.[OH-].[K+].C(C1=CC=CC=C1)=O.C(CCC)=O>>C(C1=CC=CC=C1)=C(C=O)CC | [CH3:1][CH2:2][CH2:3][CH:4]=[O:5].O=[CH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][CH2:2][C:3]([CH:4]=[O:5])=[CH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | CCCC=O.O=Cc1ccccc1 | CCC(C=O)=Cc1ccccc1 | null | null | CCO | C-C Coupling | OtherReaction | 154f038b7f5648ae5349abff8a924c982177f620bdfb6a2f53d7ca0fce37c68d | 3174a51604157c488f07402e36f994f716989b8fc10687ee243713b4cfbdb11a | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6]-[CH2;D2;+0:7]-[C:8]=[O;D1;H0:9]>>[C;D1;H3:5]-[C:6]-[C;H0;D3;+0:7](-[C:8]=[O;D1;H0:9])=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 70 | [{"value": 70.0, "product": "C(C1=CC=CC=C1)=C(C=O)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | 30.0 mL Benzaldehyde was dissolved in 150 mL EtOH and cooled with an ice bath. Added was 5.01 mL 45% KOH (0.2 equiv.), followed by dropwise addition of 16.5 mL butyraldehyde. The mixture was stirred for 3 days at room temperature, acidified with 1M HCl and extracted with ether. The organic layer was dried over Na2SO4, ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde | Aldehyde | null | null | c1ccccc1 | HO- | CCO | null | 72 | CCCC=O.O=Cc1ccccc1>CCO>CCC(C=O)=Cc1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6b9c95a31ad94f898252eaa163b5a2a7 | CCC(C=O)=Cc1ccccc1.NN>>CCC1C=NNC1c1ccccc1 | O.NN.C(C1=CC=CC=C1)=C(C=O)CC.O>>C(C)C1C=NNC1C1=CC=CC=C1 | O=[CH:4][C:3]([CH2:2][CH3:1])=[CH:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1.[NH2:5][NH2:6]>>[CH3:1][CH2:2][CH:3]1[CH:4]=[N:5][NH:6][CH:7]1[c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1 | CCC(C=O)=Cc1ccccc1.NN | CCC1C=NNC1c1ccccc1 | null | null | C(C)OCC.CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | e6b0a90bdf5439b0bafd80ec758c59b627b7e6dc79c973ee1b2fae667e8d9d63 | c3cbc07b90655a7aa9777b584274a03a2ec0cff34c5b5edc214a16916fe29f1c | C1=NNC(c2ccccc2)C1 | O=[CH;D2;+0:1]-[C;H0;D3;+0:2](-[C:3]-[C;D1;H3:4])=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8].[NH2;D1;+0:9]-[NH2;D1;+0:10]>>[C;D1;H3:4]-[C:3]-[CH;D3;+0:2]1-[CH;D2;+0:1]=[N;H0;D2;+0:9]-[NH;D2;+0:10]-[CH;D3;+0:5]-1-[c:6](:[c:7]):[c:8] | 94 | [{"value": 94.0, "product": "C(C)C1C=NNC1C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 3 | HOUR | 62 ml (10 equiv.) hydrazine hydrate was added to 150 mL diethylether. The emulsion was cooled with an ice/NaCl bath to −10° C. A solution of 20.4 g 2-benzylidene-butyraldehyde in 100 mL ether was added dropwise at −10° C. and stirred at −10° C. for 3 hours. The mixture was stirred overnight (with ice bath) and allowed ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aldehyde | Hydrazone | null | C1=NNCC1 | C1=NNCC1.c1ccccc1 | HO- | C(C)OCC.CCOCC | -10 | 3 | CCC(C=O)=Cc1ccccc1.NN>C(C)OCC.CCOCC>CCC1C=NNC1c1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2e554649f6b9407aa6af9dc843fd250c | COC(=O)C1=CCCN(C)C1>>CN1CCC=C(CO)C1 | COC(=O)C=1CN(CCC1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+].O>>CN1CC(=CCC1)CO | CO[C:7]([C:6]1=[CH:5][CH2:4][CH2:3][N:2]([CH3:1])[CH2:9]1)=[O:8]>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]=[C:6]([CH2:7][OH:8])[CH2:9]1 | COC(=O)C1=CCCN(C)C1 | CN1CCC=C(CO)C1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1=CCNCC1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](=[C:4]-[C:5])-[C:6]-[#7:7]>>[#7:7]-[C:6]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])=[C:4]-[C:5] | 98.9 | [{"value": 98.9, "product": "CN1CC(=CCC1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | 6.5 g of LiAlH4 (3.2 equiv.) was suspended in 100 mL dry THF and cooled with an ice bath. To this was added dropwise a solution of 8.27 g 1-Methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester (free base) in 50 mL dry THF. The mixture was stirred for 3 hours at room temperature. The mixture was cooled with... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | C1=CC[NH]CC1 | Other | C1CCOC1 | null | 3 | COC(=O)C1=CCCN(C)C1>C1CCOC1>CN1CCC=C(CO)C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-38568b8d6b4c4702808be1e41b377b58 | CN1CCC=C(CO)C1>>CN1CCC=C(C=O)C1 | C(C)N(CC)CC.CN1CC(=CCC1)CO.C(C(=O)Cl)(=O)Cl.CS(=O)C>>CN1CC(=CCC1)C=O | [CH3:1][N:2]1[CH2:3][CH2:4][CH:5]=[C:6]([CH2:7][OH:8])[CH2:9]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]=[C:6]([CH:7]=[O:8])[CH2:9]1 | CN1CCC=C(CO)C1 | CN1CCC=C(C=O)C1 | null | null | O.C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | C1=CCNCC1 | [#7:1]-[C:2]-[C:3](-[CH2;D2;+0:4]-[OH;D1;+0:5])=[C:6]-[C:7]>>[#7:1]-[C:2]-[C:3](-[CH;D2;+0:4]=[O;H0;D1;+0:5])=[C:6]-[C:7] | 109.7 | [{"value": 85.0, "product": "CN1CC(=CCC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 109.7, "product": "CN1CC(=CCC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 15 | MINUTE | 2.88 mL oxalyl chloride (2.4 equiv.) was dissolved in 20 mL DCM. The mixture was cooled to −78° C. and a solution of 3.37 mL DMSO (2.0 equiv.) in 10 mL DCM was added dropwise. The mixture was stirred for 15 minutes at −78° C. A solution of 3.0 g (1-Methyl-1,2,5,6-tetrahydro-pyridin-3-yl)-methanol in 10 mL DCM was added... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1=CC[NH]CC1 | null | O.C(Cl)Cl | -78 | 0.25 | CN1CCC=C(CO)C1>O.C(Cl)Cl>CN1CCC=C(C=O)C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-67e561b31978414c8fcba4efacbbcbe9 | CN1CCC=C(C=O)C1.NN>>CN1CCC2NN=CC2C1 | CN1CC(=CCC1)C=O.O.NN>>CN1CC2C(CC1)NN=C2 | O=[CH:8][C:9]1=[CH:5][CH2:4][CH2:3][N:2]([CH3:1])[CH2:10]1.[NH2:6][NH2:7]>>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]2[NH:6][N:7]=[CH:8][CH:9]2[CH2:10]1 | CN1CCC=C(C=O)C1.NN | CN1CCC2NN=CC2C1 | null | null | CCCCO | Heteroatom Alkylation and Arylation | OtherReaction | aa23589c91b6f94ddd92d866429ce13046adef19dfcbac63f7429913b3bb475a | c3cbc07b90655a7aa9777b584274a03a2ec0cff34c5b5edc214a16916fe29f1c | C1=NNC2CCNCC12 | O=[CH;D2;+0:1]-[C;H0;D3;+0:2]1=[CH;D2;+0:3]-[C:4]-[C:5]-[#7:6](-[C;D1;H3:7])-[C:8]-1.[NH2;D1;+0:9]-[NH2;D1;+0:10]>>[C;D1;H3:7]-[#7:6]1-[C:8]-[CH;D3;+0:2]2-[CH;D2;+0:1]=[N;H0;D2;+0:10]-[NH;D2;+0:9]-[CH;D3;+0:3]-2-[C:4]-[C:5]-1 | null | [] | null | null | null | null | 3.2 g 1-Methyl-1,2,5,6-tetrahydro-pyridine-3-carbaldehyde was dissolved in 10 mL n-BuOH. Added were 2 equiv. of hydrazine hydrate, the mixture was refluxed for 24 hours and subsequently concentrated in vacuo. The residue was taken up in DCM and extracted with 2M NaOH, and the organic phase was dried over Na2SO4, filtra... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aldehyde | Hydrazone | C1=CC[NH]CC1 | C1=NNC2CC[NH]CC12 | C1=NNC2CC[NH]CC12 | HO- | CCCCO | null | null | CN1CCC=C(C=O)C1.NN>CCCCO>CN1CCC2NN=CC2C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-bb9528bd65444948971ae1d9ea7916a5 | BrCc1ccccc1.ClCCNCCCl>>ClCCN(CCCl)Cc1ccccc1 | Cl.ClCCNCCCl.C(=O)([O-])[O-].[K+].[K+].C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)N(CCCl)CCCl | Br[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.[Cl:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][Cl:7]>>[Cl:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][Cl:7])[CH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1 | BrCc1ccccc1.ClCCNCCCl | ClCCN(CCCl)Cc1ccccc1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 6d58cac08ccced0a33ed16fbca180bc12aa011288d6476106d98a7b2cbc3d709 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]>>[C:5]-[C:6]-[N;H0;D3;+0:7](-[C:8]-[C:9])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | Bis-(2-chloro-ethyl)-amine hydrochloride was suspended in 150 mL acetonitrile. Added were 34.8 g K2CO3 (3 equiv.) and 10.0 mL benzylbromide (1 equiv.). The mixture was refluxed overnight, Concentration on silica and purification with flash column chromatography (eluents PA:ether=95:5) yielded 4.11 g of a colorless oil.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | null | null | c1ccccc1 | HBr | C(C)#N | null | null | BrCc1ccccc1.ClCCNCCCl>C(C)#N>ClCCN(CCCl)Cc1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6be78afd8b93470f9bf3cd37eaa8369d | NCC1(CN)CCN(Cc2ccccc2)CC1>>c1ccc(CN2CCC3(CC2)CN=NC3)cc1 | NCC1(CCN(CC1)CC1=CC=CC=C1)CN.CO.OO.[O-]Cl.[Na+]>>C(C1=CC=CC=C1)N1CCC2(CN=NC2)CC1 | [cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][C:9]([CH2:12][NH2:13])([CH2:15][NH2:14])[CH2:10][CH2:11]2)[cH:16][cH:17]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][N:6]2[CH2:7][CH2:8][C:9]3([CH2:10][CH2:11]2)[CH2:12][N:13]=[N:14][CH2:15]3)[cH:16][cH:17]1 | NCC1(CN)CCN(Cc2ccccc2)CC1 | c1ccc(CN2CCC3(CC2)CN=NC3)cc1 | null | null | O | Oxidation | OtherReaction | 18390025a7adc4519b7a462816c7c35329fdd2c4c87c461cd30a333c3a79b596 | ccb08cdd906ab1c43b965b3f381a9df42e8b4b6ec4217dac787b89befda7069c | c1ccc(CN2CCC3(CC2)CN=NC3)cc1 | [NH2;D1;+0:1]-[C:2]-[C:3]-[C:4]-[NH2;D1;+0:5]>>[C:2]1-[C:3]-[C:4]-[N;H0;D2;+0:5]=[N;H0;D2;+0:1]-1 | 90.3 | [{"value": 90.3, "product": "C(C1=CC=CC=C1)N1CCC2(CN=NC2)CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2.48 g of C-(4-Aminomethyl-1-benzyl-piperidin-4-yl)-methylamine was suspended in 40 mL H2O and 10 mL MeOH and cooled with an ice bath. Simultaneously, 6.7 mL 30% H2O2 (6 equiv.) and 15.2 mL 10% NaClO (2.4 equiv.) were added dropwise. The mixture was stirred at room temperature for 1 hour. The mixture was extracted 2 ti... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Diazene | null | C1CC2(CC[NH]1)CN=NC2 | c1ccccc1.C1CC2(CC[NH]1)CN=NC2 | null | O | null | 1 | NCC1(CN)CCN(Cc2ccccc2)CC1>O>c1ccc(CN2CCC3(CC2)CN=NC3)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-bddcae2aae8a4f21aa0a7311799b508a | CC(C#N)(C#N)COCc1ccccc1>>CC(CN)(CN)COCc1ccccc1 | C(C1=CC=CC=C1)OCC(C#N)(C#N)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+].O>>C(C1=CC=CC=C1)OCC(CN)(CN)C | [CH3:1][C:2]([C:3]#[N:4])([C:5]#[N:6])[CH2:7][O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][C:2]([CH2:3][NH2:4])([CH2:5][NH2:6])[CH2:7][O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | CC(C#N)(C#N)COCc1ccccc1 | CC(CN)(CN)COCc1ccccc1 | null | null | C(C)OCC | Reduction | OtherReaction | c2340da2c258bf397d4a8fa28e5be42ecf34d1d4e5e541c0aa9e06499bdba3ed | cb8a07357b502aa07f8272954f5a9149eabfa75b76e8c8c18ad60272c8d4f167 | c1ccccc1 | [C:1]-[C:2](-[C;D1;H3:3])(-[C;H0;D2;+0:4]#[N;H0;D1;+0:5])-[C;H0;D2;+0:6]#[N;H0;D1;+0:7]>>[C:1]-[C:2](-[C;D1;H3:3])(-[CH2;D2;+0:4]-[NH2;D1;+0:5])-[CH2;D2;+0:6]-[NH2;D1;+0:7] | 92.9 | [{"value": 84.0, "product": "C(C1=CC=CC=C1)OCC(CN)(CN)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.9, "product": "C(C1=CC=CC=C1)OCC(CN)(CN)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | LiAlH4 (3.22 g; 84.84 mmol; 3.0 equiv.) was suspended in 30 mL dry diethylether and cooled with an ice bath. A solution of 2-Benzyloxymethyl-2-methyl-malononitrile (5.72 g; 28.28 mmol; 1.0 equiv.) in 20 mL dry diethylether was added dropwise. The suspension was stirred at room temperature for 4 hours, and subsequently ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Nitrile | Primary amine.Primary amine | null | null | c1ccccc1 | null | C(C)OCC | null | 4 | CC(C#N)(C#N)COCc1ccccc1>C(C)OCC>CC(CN)(CN)COCc1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-4052a6dbde5847328dbec77949a0b930 | BrCCOCCBr.N#CCC#N>>N#CC1(C#N)CCOCC1 | C(CC#N)#N.BrCCOCCBr.CC(C)(C)[O-].[K+]>>O1CCC(CC1)(C#N)C#N | Br[CH2:6][CH2:7][O:8][CH2:9][CH2:10]Br.[N:1]#[C:2][CH2:3][C:4]#[N:5]>>[N:1]#[C:2][C:3]1([C:4]#[N:5])[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1 | BrCCOCCBr.N#CCC#N | N#CC1(C#N)CCOCC1 | null | CCCC[N+](CCCC)(CCCC)CCCC.[Br-] | CS(=O)C.C(Cl)Cl | C-C Coupling | OtherReaction | 7a02bf4931a2667c7a560f7e10856bd80597aeb566d8b87c38850fad3f2124c8 | 7b68950fc1047c59bb49c25e850f5a51cbe91a99bb87839c4547aec123110e4b | C1CCOCC1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-Br.[N;D1;H0:6]#[C:7]-[CH2;D2;+0:8]-[C:9]#[N;D1;H0:10]>>[N;D1;H0:6]#[C:7]-[C;H0;D4;+0:8]1(-[C:9]#[N;D1;H0:10])-[CH2;D2;+0:1]-[C:2]-[#8:3]-[C:4]-[CH2;D2;+0:5]-1 | 24 | [{"value": 24.0, "product": "O1CCC(CC1)(C#N)C#N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | Malononitrile (5.0 g) was dissolved in DMSO (5 mL). Subsequently, bis(2-bromoethyl)ether (9.49 mL) and TBAB (1.22 g) were added, followed by portionwise addition of KOtBu (8.49 g). The mixture was stirred for 4 h. at room temperature, taken up in DCM and extracted 3 times with 5% aqueous NaHCO3. The organic phase was d... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide | null | null | C1CCOCC1 | C1CCOCC1 | HBr | CCCC[N+](CCCC)(CCCC)CCCC.[Br-].CS(=O)C.C(Cl)Cl | null | 4 | BrCCOCCBr.N#CCC#N>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].CS(=O)C.C(Cl)Cl>N#CC1(C#N)CCOCC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b024ed43abc34f699c2cabd633dfb5f9 | N#CC1(C#N)CCOCC1>>NCC1(CN)CCOCC1 | B.C1CCOC1.[OH-].[Na+].Cl.O1CCC(CC1)(C#N)C#N>>NCC1(CCOCC1)CN | [N:1]#[C:2][C:3]1([C:4]#[N:5])[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1>>[NH2:1][CH2:2][C:3]1([CH2:4][NH2:5])[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1 | N#CC1(C#N)CCOCC1 | NCC1(CN)CCOCC1 | null | null | C1CCOC1 | Reduction | OtherReaction | c2340da2c258bf397d4a8fa28e5be42ecf34d1d4e5e541c0aa9e06499bdba3ed | cb8a07357b502aa07f8272954f5a9149eabfa75b76e8c8c18ad60272c8d4f167 | C1CCOCC1 | [C:1]-[C:2](-[C;H0;D2;+0:3]#[N;H0;D1;+0:4])(-[C;H0;D2;+0:5]#[N;H0;D1;+0:6])-[C:7]>>[C:1]-[C:2](-[CH2;D2;+0:3]-[NH2;D1;+0:4])(-[CH2;D2;+0:5]-[NH2;D1;+0:6])-[C:7] | 62.1 | [{"value": 62.0, "product": "NCC1(CCOCC1)CN", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.1, "product": "NCC1(CCOCC1)CN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 6 | HOUR | Tetrahydro-pyran-4,4-dicarbonitrile (1.52 g) was dissolved in dry THF (25 mL) and cooled to −10° C. To this solution, BH3.THF (56 mL of an 1M solution in THF, 5 equiv.) was added dropwise, the mixture was allowed to warm to room temperature, and subsequently stirred at 60° C. for 6 h. The mixture was cooled in an ice b... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Nitrile | Primary amine.Primary amine | null | null | C1CCOCC1 | null | C1CCOC1 | -10 | 6 | N#CC1(C#N)CCOCC1>C1CCOC1>NCC1(CN)CCOCC1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f33760f47a354d128b5ea74e5ca6a297 | NCC1(CN)CCOCC1>>C1CC2(CCO1)CN=NC2 | NCC1(CCOCC1)CN.OO.[O-]Cl.[Na+]>>C1N=NCC12CCOCC2 | [CH2:1]1[CH2:2][C:3]([CH2:7][NH2:8])([CH2:10][NH2:9])[CH2:4][CH2:5][O:6]1>>[CH2:1]1[CH2:2][C:3]2([CH2:4][CH2:5][O:6]1)[CH2:7][N:8]=[N:9][CH2:10]2 | NCC1(CN)CCOCC1 | C1CC2(CCO1)CN=NC2 | null | null | CO.O | Oxidation | OtherReaction | b039614aa0942bb786d1e3503d67dcda1e3cab33aa92d388b060f46889f55ddf | ccb08cdd906ab1c43b965b3f381a9df42e8b4b6ec4217dac787b89befda7069c | C1CC2(CCO1)CN=NC2 | [NH2;D1;+0:1]-[C:2]-[C:3]-[C:4]-[NH2;D1;+0:5]>>[C:4]1-[C:3]-[C:2]-[N;H0;D2;+0:1]=[N;H0;D2;+0:5]-1 | 85 | [{"value": 85.0, "product": "C1N=NCC12CCOCC2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | C-(4-Aminomethyl-tetrahydro-pyran-4-yl)-methylamine (1.0 g) was taken up in a mixture of H2O (10 mL) and MeOH (2.5 mL), and cooled in an ice bath. Simultaneously, H2O2 (4.8 mL of a 30% solution, 6 equiv.) and NaClO (12.4 mL of a 10% solution, 2.4 equiv.) were added dropwise, the ice bath was removed, and the mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Diazene | null | C1CC2(CCO1)CN=NC2 | C1CC2(CCO1)CN=NC2 | null | CO.O | null | 8 | NCC1(CN)CCOCC1>CO.O>C1CC2(CCO1)CN=NC2 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a23d62bb03b44b8aa4bbb58712329041 | FC(F)(F)CCI.N#CCC#N>>N#CC(C#N)(CC(F)(F)F)CC(F)(F)F | C(CC#N)#N.ICCC(F)(F)F.[H-].[Na+]>>FC(CC(C#N)(C#N)CC(F)(F)F)(F)F | I[CH2:11][CH2:6][C:7]([F:8])([F:10])[F:13].[N:1]#[C:2][CH2:3][C:4]#[N:5]>>[N:1]#[C:2][C:3]([C:4]#[N:5])([CH2:6][C:7]([F:8])([F:9])[F:10])[CH2:11][C:12]([F:13])([F:14])[F:15] | FC(F)(F)CCI.N#CCC#N | N#CC(C#N)(CC(F)(F)F)CC(F)(F)F | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 80ce7b97e36b0c0ec774726a0bcfd7a54bd6e39c8df554aa1de887d8048dad37 | 7c1d2c8d4ceba55eeb3a66322d758dc06aaff7a8226b4e829e78570c406fb155 | null | I-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[C;H0;D4;+0:3](-[F;D1;H0:4])(-[F;D1;H0:5])-[F;H0;D1;+0:6].[N;D1;H0:7]#[C:8]-[CH2;D2;+0:9]-[C:10]#[N;D1;H0:11]>>[F;D1;H0:4]-[C;H0;D4;+0:3](-[F;D1;H0:5])(-[F;D1;H0:12])-[CH2;D2;+0:2]-[C;H0;D4;+0:9](-[C:8]#[N;D1;H0:7])(-[C:10]#[N;D1;H0:11])-[CH2;D2;+0:1]-[C:13](-[F;D1;H0:14])(-[F;D1;H0:15])-[... | 16.4 | [{"value": 16.4, "product": "FC(CC(C#N)(C#N)CC(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Malononitril (20.15 mmol) and 1-iodo-3,3,3-trifluoropropane (42.65 mmol) were dissolved in 30 ml dry THF, and the mixture was cooled with an ice/salt bath. 1.61 g NaH (40.3 mmol) was added portionwise, keeping the temperature below 5° C. The reaction mixture was stirred at room temperature for 2 hours and evaporated un... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Primary halide | Trifluoro group.Trifluoro group | null | null | null | HI | C1CCOC1 | null | 2 | FC(F)(F)CCI.N#CCC#N>C1CCOC1>N#CC(C#N)(CC(F)(F)F)CC(F)(F)F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-1ce3f963d5cc4f66ad04c748a392f7d0 | N#CC(C#N)(CC(F)(F)F)CC(F)(F)F>>NCC(CN)(CC(F)(F)F)CC(F)(F)F | [H-].[H-].[H-].[H-].[Li+].[Al+3].FC(CC(C#N)(C#N)CC(F)(F)F)(F)F>>FC(CC(CN)(CN)CC(F)(F)F)(F)F | [N:1]#[C:2][C:3]([C:4]#[N:5])([CH2:6][C:7]([F:8])([F:9])[F:10])[CH2:11][C:12]([F:13])([F:14])[F:15]>>[NH2:1][CH2:2][C:3]([CH2:4][NH2:5])([CH2:6][C:7]([F:8])([F:9])[F:10])[CH2:11][C:12]([F:13])([F:14])[F:15] | N#CC(C#N)(CC(F)(F)F)CC(F)(F)F | NCC(CN)(CC(F)(F)F)CC(F)(F)F | null | null | CCOCC | Reduction | OtherReaction | c2340da2c258bf397d4a8fa28e5be42ecf34d1d4e5e541c0aa9e06499bdba3ed | cb8a07357b502aa07f8272954f5a9149eabfa75b76e8c8c18ad60272c8d4f167 | null | [C:1]-[C:2](-[C:3])(-[C;H0;D2;+0:4]#[N;H0;D1;+0:5])-[C;H0;D2;+0:6]#[N;H0;D1;+0:7]>>[C:1]-[C:2](-[C:3])(-[CH2;D2;+0:4]-[NH2;D1;+0:5])-[CH2;D2;+0:6]-[NH2;D1;+0:7] | 91.5 | [{"value": 91.5, "product": "FC(CC(CN)(CN)CC(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 340 mg LiAlH4 (8.95 mmol) was suspended in 15 ml dry Et2O and cooled in an ice bath. A solution of 760 mg 2,2-Bis-(2,2,2-trifluoro-ethyl)-malononitrile in Et2O was added dropwise at such a rate that the temperature was kept below 20° C. The mixture was stirred overnight at room temperature, cooled in an ice bath, and q... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Nitrile | Primary amine.Primary amine | null | null | null | null | CCOCC | null | 8 | N#CC(C#N)(CC(F)(F)F)CC(F)(F)F>CCOCC>NCC(CN)(CC(F)(F)F)CC(F)(F)F |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ac56c7d916db4ddcb9163798bf19af4e | COC(=O)Cl.NS(=O)(=O)c1ccccc1Cl>>COC(=O)NS(=O)(=O)c1ccccc1Cl | ClC(=O)OC.ClC1=C(C=CC=C1)S(=O)(=O)N.C(C)N(CC)CC>>COC(NS(=O)(=O)C1=C(C=CC=C1)Cl)=O | Cl[C:3]([O:2][CH3:1])=[O:4].[NH2:5][S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[Cl:15]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[Cl:15] | COC(=O)Cl.NS(=O)(=O)c1ccccc1Cl | COC(=O)NS(=O)(=O)c1ccccc1Cl | null | null | C(C)#N | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 2f2696288009d2012d9ec2995f8be43c58fdee99389b7d218ed77c4bafda7b17 | 60493cac785f670383c62b059214a5eb4def232e11814f271849329f2f6b7966 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C;D1;H3:4].[NH2;D1;+0:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9]>>[C;D1;H3:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[#16:6](=[O;D1;H0:7])(=[O;D1;H0:8])-[c:9] | null | [] | null | null | 8 | HOUR | To 25.0 g 2-chloro-benzenesulfonamide was added 75 mL acetonitrile and 45.2 mL (2.5 eq) triethylamine. The mixture was cooled with an ice bath and 15.1 mL methyl chloroformate was slowly added dropwise. The mixture was stirred overnight at room temperature and concentrated in vacuo. Water was added and de aqueous layer... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Sulfonamide | Sulfonamide.Carbamic ester | null | null | c1ccccc1 | HCl | C(C)#N | null | 8 | COC(=O)Cl.NS(=O)(=O)c1ccccc1Cl>C(C)#N>COC(=O)NS(=O)(=O)c1ccccc1Cl |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e6f8b38247c34282b73c14f8fb70fdee | CCC1C=NNC1.CSC(=NS(=O)(=O)c1ccccc1Cl)SC>>CCC1C=NN(SC(C)=NS(=O)(=O)c2ccccc2Cl)C1 | C(C)C1C=NNC1.N1=CC=CC=C1.CSC(=NS(=O)(=O)C1=C(C=CC=C1)Cl)SC>>ClC1=C(C=CC=C1)S(=O)(=O)N=C(SN1N=CC(C1)CC)C | [CH3:1][CH2:2][CH:3]1[CH:4]=[N:5][NH:6][CH2:21]1.C[S:7][C:8](S[CH3:9])=[N:10][S:11](=[O:12])(=[O:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][c:19]1[Cl:20]>>[CH3:1][CH2:2][CH:3]1[CH:4]=[N:5][N:6]([S:7][C:8]([CH3:9])=[N:10][S:11](=[O:12])(=[O:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[Cl:20])[CH2:21]1 | CCC1C=NNC1.CSC(=NS(=O)(=O)c1ccccc1Cl)SC | CCC1C=NN(SC(C)=NS(=O)(=O)c2ccccc2Cl)C1 | null | null | null | C-C Coupling | OtherReaction | 8d8b038879f9ae3e1763bb6b094352cbfbed836bcad13bd5634b2dfd4485a184 | ba9da9a3c58c760c9d311761733b7830676bada377cf8304c7fe9c76e3ef2110 | O=S(=O)(N=CSN1CCC=N1)c1ccccc1 | C-[S;H0;D2;+0:1]-[C;H0;D3;+0:2](-S-[CH3;D1;+0:3])=[#7:4]-[#16:5].[#7:6]1=[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[#16:5]-[#7:4]=[C;H0;D3;+0:2](-[CH3;D1;+0:3])-[S;H0;D2;+0:1]-[N;H0;D3;+0:10]1-[#7:6]=[C:7]-[C:8]-[C:9]-1 | null | [] | null | null | null | null | 500 mg 4-Ethyl-4,5-dihydro-1H-pyrazole was dissolved in 10 mL pyridine. 1.51 g N-(Bis-methylsulfanyl-methylene)-2-chloro-benzenesulfonamide was added and the mixture was refluxed overnight. The mixture was concentrated in vacuo and H2O was added, followed by extraction twice with DCM. The combined organic layers were d... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Monosulfide.Monosulfide | Hydrazone.Monosulfide | C1=NNCC1 | C1=N[NH]CC1 | C1=N[NH]CC1.c1ccccc1 | Other | null | null | null | CCC1C=NNC1.CSC(=NS(=O)(=O)c1ccccc1Cl)SC>>CCC1C=NN(SC(C)=NS(=O)(=O)c2ccccc2Cl)C1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ee39ee2d9b114f3a936d102e63da2c71 | CCNC(=N)N1CC(CC)C=N1.O=S(=O)(Cl)c1cccc2nsnc12>>CCNC(=NS(=O)(=O)c1cccc2nsnc12)N1CC(CC)C=N1 | Cl.C(C)C1C=NN(C1)C(=N)NCC.CCN(C(C)C)C(C)C.N1=C2C(=NS1)C(=CC=C2)S(=O)(=O)Cl>>C(C)NC(=NS(=O)(=O)C1=CC=CC=2C1=NSN2)N2N=CC(C2)CC | [CH3:1][CH2:2][NH:3][C:4](=[NH:5])[N:18]1[CH2:19][CH:20]([CH2:21][CH3:22])[CH:23]=[N:24]1.Cl[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][s:15][n:16][c:17]12>>[CH3:1][CH2:2][NH:3][C:4](=[N:5][S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]2[n:14][s:15][n:16][c:17]12)[N:18]1[CH2:19][CH:20]([CH2:21]... | CCNC(=N)N1CC(CC)C=N1.O=S(=O)(Cl)c1cccc2nsnc12 | CCNC(=NS(=O)(=O)c1cccc2nsnc12)N1CC(CC)C=N1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 65bd520d46095381b97cf2b1c808b198594dded087e2637f2dbe5add6a47838a | 5f0d826ff827e7d94d07bc9ee74d0a88c79bcf75bb024f05043486e1cbe294bd | O=S(=O)(N=CN1CCC=N1)c1cccc2nsnc12 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]1:[#7;a:7]:[#16;a:8]:[#7;a:9]:[c:10]:1.[#7:11]-[#7:12]-[C:13](-[#7:14])=[NH;D1;+0:15]>>[#7:11]-[#7:12]-[C:13](-[#7:14])=[N;H0;D2;+0:15]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]1:[#7;a:7]:[#16;a:8]:[#7;a:9]:[c:10]:1 | 84.7 | [{"value": 84.7, "product": "C(C)NC(=NS(=O)(=O)C1=CC=CC=2C1=NSN2)N2N=CC(C2)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 300 mg 4,N-Diethyl-4,5-dihydro-pyrazole-1-carboxamidine hydrochloride was suspended in 10 mL DCM. 0.53 mL DiPEA and 310 mg benzo[1,2,5]thiadiazole-4-sulfonylchloride were added and the mixture was stirred overnight at room temperature. The mixture was washed with 5% NaHCO3 and 2 M NaOH, the organic layer dried over Na2... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | null | null | c1ccc2nsnc2c1.C1=N[NH]CC1 | HCl | C(Cl)Cl | null | 8 | CCNC(=N)N1CC(CC)C=N1.O=S(=O)(Cl)c1cccc2nsnc12>C(Cl)Cl>CCNC(=NS(=O)(=O)c1cccc2nsnc12)N1CC(CC)C=N1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f74a5cfdc3c645d594fa518fd94b6452 | CCNC(=N)N1CC(C)(C)C=N1.O=S(=O)(Cl)c1cccc(Cl)c1>>CCNC(=NS(=O)(=O)c1cccc(Cl)c1)N1CC(C)(C)C=N1 | Cl.C(C)NC(=N)N1N=CC(C1)(C)C.CCN(C(C)C)C(C)C.ClC=1C=C(C=CC1)S(=O)(=O)Cl>>ClC=1C=C(C=CC1)S(=O)(=O)N=C(NCC)N1N=CC(C1)(C)C | [CH3:1][CH2:2][NH:3][C:4](=[NH:5])[N:16]1[CH2:17][C:18]([CH3:19])([CH3:20])[CH:21]=[N:22]1.Cl[S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([Cl:14])[cH:15]1>>[CH3:1][CH2:2][NH:3][C:4](=[N:5][S:6](=[O:7])(=[O:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([Cl:14])[cH:15]1)[N:16]1[CH2:17][C:18]([CH3:19])([CH3:20])[CH:21]=[... | CCNC(=N)N1CC(C)(C)C=N1.O=S(=O)(Cl)c1cccc(Cl)c1 | CCNC(=NS(=O)(=O)c1cccc(Cl)c1)N1CC(C)(C)C=N1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 65bd520d46095381b97cf2b1c808b198594dded087e2637f2dbe5add6a47838a | 5f0d826ff827e7d94d07bc9ee74d0a88c79bcf75bb024f05043486e1cbe294bd | O=S(=O)(N=CN1CCC=N1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#7:7]-[#7:8]-[C:9](-[#7:10])=[NH;D1;+0:11]>>[#7:7]-[#7:8]-[C:9](-[#7:10])=[N;H0;D2;+0:11]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 20 | HOUR | 6.39 g N-Ethyl-4,4-dimethyl-4,5-dihydro-pyrazole-1-carboxamidine hydrochloride was suspended in 65 mL DCM. 12.0 mL DIPEA and 3.96 mL 3-chloro-benzenesulfonyl chloride were added and the suspension was stirred for 20 h. at room temperature, resulting in a dark brown turbid solution. The mixture was extracted with 2M NaO... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide | null | null | null | c1ccccc1.C1=N[NH]CC1 | HCl | C(Cl)Cl | null | 20 | CCNC(=N)N1CC(C)(C)C=N1.O=S(=O)(Cl)c1cccc(Cl)c1>C(Cl)Cl>CCNC(=NS(=O)(=O)c1cccc(Cl)c1)N1CC(C)(C)C=N1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ec8adad63d0041a0969484598bc2e2fd | Cc1ccc(Br)cc1.[C-]#Cc1ccccc1>>Cc1ccc(C#Cc2ccccc2)cc1 | BrC1=CC=C(C=C1)C.[Li+].[C-]#CC1=CC=CC=C1.O(C(C)C)B(OC(C)C)OC(C)C>>C1(=CC=C(C=C1)C#CC1=CC=CC=C1)C | Br[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:15][cH:14]1.[C-:6]#[C:7][c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]#[C:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][cH:15]1 | Cc1ccc(Br)cc1.[C-]#Cc1ccccc1 | Cc1ccc(C#Cc2ccccc2)cc1 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC.COCCOC.C1CCOC1 | C-C Coupling | OtherReaction | 93ae246e7c863443a3aaaa90941d39ebe932c135fc33ecf39310e65c58a9fbd3 | 1e016b25438ccc05198b60acd46c3be4f5258f827b14753e63a4bafcf188d801 | C(#Cc1ccccc1)c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C-;H0;D1:6]#[C:7]-[c:8]>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[C;H0;D2;+0:6]#[C:7]-[c:8]):[c:4]:[c:5] | null | [] | -78 | CELSIUS | 1.5 | HOUR | General Procedure A. To a solution of lithium phenylacetylide (15.2 ml, 15.2 mmol) in DME (20 ml) under Argon at −78° C. was added triisopropoxylborane (3.5 ml, 15.2 mmol). The mixture was stirred at −78° C. for 1.5 hours. A solution of 1-bromo-4-methylbenzene (2 g, 11.7 mmol) in DME/THF (10 ml/10 ml) was degassed with... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC.COCCOC.C1CCOC1 | -78 | 1.5 | Cc1ccc(Br)cc1.[C-]#Cc1ccccc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC.COCCOC.C1CCOC1>Cc1ccc(C#Cc2ccccc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-407ba34a62634895800105f14ad97f06 | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccccc2)n1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccccc2)n1>>CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | C1(=CC=CC=C1)C=1N=C(N=NC1C1=CC=CC=C1)C(=O)OCC.C1(=CC=CC=C1)C=1N=C(N=NC1C1=CC=CC=C1)C(=O)OCC.C(=C)N1CCCC1.C(=C)N1CCCC1>>C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OCC | C(N1CCCC1)=[CH2:8].CCOC(=O)[c:7]1nnc(-c2ccccc2)c(-c2ccccc2)n1.n1n[c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n:23][c:6]1[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16... | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccccc2)n1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccccc2)n1 | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | cc03cad530703fa23e2ff0c67e0b9f19978525eb16d0ce01e888c853e60d70ca | c44d9ef0146168ac01b86e0d21b2b8ec8b64b9feba9682f4fc6d6e96c9b2417f | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-O-C(=O)-[c;H0;D3;+0:1]1:n:n:c(-c2:c:c:c:c:c:2):c(-c2:c:c:c:c:c:2):n:1.[CH2;D1;+0:2]=C-N1-C-C-C-C-1.[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:11](-[c:12](:[c:13]):[c:14]):n:n:1>>[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:11](-[c:12]... | null | [] | null | null | null | null | General Procedure D. Ethyl 5,6-diphenyl-1,2,4-triazine-3-carboxylate (Compound 11, 200 mg, 0.66 mmol) and crude 1-vinylpyrrolidine (Compound 38, 2 g) in CHCl3 (20 ml) was heated at 75° C. overnight under nitrogen. The solvent was removed in vacuo, and the residue was purified by silica gel column chromatography (20% et... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ester.Ester | Ester | C1CCNC1.c1cnncn1.c1ccccc1.c1ccccc1.c1cnncn1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | null | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccccc2)n1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccccc2)n1>C(Cl)(Cl)Cl>CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-0eef4f474e3b4844a43a01518b3416ad | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccc(C)cc2)c(-c2ccccc2)n1.CCOC(=O)c1nnc(-c2ccc(C)cc2)c(-c2ccccc2)n1>>CCOC(=O)c1ccc(-c2ccc(C)cc2)c(-c2ccccc2)n1 | C(=C)N1CCCC1.C1(=CC=CC=C1)C=1N=C(N=NC1C1=CC=C(C=C1)C)C(=O)OCC.C1(=CC=CC=C1)C=1N=C(N=NC1C1=CC=C(C=C1)C)C(=O)OCC.C(=C)N1CCCC1>>C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OCC)C1=CC=C(C=C1)C | C(N1CCCC1)=[CH2:8].CCOC(=O)[c:7]1nnc(-c2ccc(C)cc2)c(-c2ccccc2)n1.n1n[c:9](-[c:10]2[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]2)[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24][c:6]1[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([CH3:14])... | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccc(C)cc2)c(-c2ccccc2)n1.CCOC(=O)c1nnc(-c2ccc(C)cc2)c(-c2ccccc2)n1 | CCOC(=O)c1ccc(-c2ccc(C)cc2)c(-c2ccccc2)n1 | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | cc03cad530703fa23e2ff0c67e0b9f19978525eb16d0ce01e888c853e60d70ca | c44d9ef0146168ac01b86e0d21b2b8ec8b64b9feba9682f4fc6d6e96c9b2417f | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-O-C(=O)-[c;H0;D3;+0:1]1:n:n:c(-c2:c:c:c(-C):c:c:2):c(-c2:c:c:c:c:c:2):n:1.[CH2;D1;+0:2]=C-N1-C-C-C-C-1.[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:11](-[c:12](:[c:13]):[c:14]):n:n:1>>[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:11](-[c... | null | [] | null | null | null | null | Following General Procedure D, ethyl 5-phenyl-6-p-tolyl-1,2,4-triazine-3-carboxylate (Compound 12, 177 mg, 0.56 mmol) and crude 1-vinylpyrrolidine (Compound 38, 730 mg) in CHCl3 (10 ml) were reacted to produce the title compound as a yellow solid.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ester.Ester | Ester | C1CCNC1.c1cnncn1.c1ccccc1.c1ccccc1.c1cnncn1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | null | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccc(C)cc2)c(-c2ccccc2)n1.CCOC(=O)c1nnc(-c2ccc(C)cc2)c(-c2ccccc2)n1>C(Cl)(Cl)Cl>CCOC(=O)c1ccc(-c2ccc(C)cc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ff9619e76cab447082841ad9a3fd4058 | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccc(CC)cc2)c(-c2ccccc2)n1.CCOC(=O)c1nnc(-c2ccc(CC)cc2)c(-c2ccccc2)n1>>CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccccc2)n1 | C(=C)N1CCCC1.C(C)C1=CC=C(C=C1)C1=C(N=C(N=N1)C(=O)OCC)C1=CC=CC=C1.C(C)C1=CC=C(C=C1)C1=C(N=C(N=N1)C(=O)OCC)C1=CC=CC=C1.C(=C)N1CCCC1>>C(C)C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OCC | C(N1CCCC1)=[CH2:8].CCOC(=O)[c:7]1nnc(-c2ccc(CC)cc2)c(-c2ccccc2)n1.n1n[c:9](-[c:10]2[cH:11][cH:12][c:13]([CH2:14][CH3:15])[cH:16][cH:17]2)[c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[n:25][c:6]1[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13](... | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccc(CC)cc2)c(-c2ccccc2)n1.CCOC(=O)c1nnc(-c2ccc(CC)cc2)c(-c2ccccc2)n1 | CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccccc2)n1 | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | cc03cad530703fa23e2ff0c67e0b9f19978525eb16d0ce01e888c853e60d70ca | c44d9ef0146168ac01b86e0d21b2b8ec8b64b9feba9682f4fc6d6e96c9b2417f | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-O-C(=O)-[c;H0;D3;+0:1]1:n:n:c(-c2:c:c:c(-C-C):c:c:2):c(-c2:c:c:c:c:c:2):n:1.[CH2;D1;+0:2]=C-N1-C-C-C-C-1.[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:11](-[c:12](:[c:13]):[c:14]):n:n:1>>[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:11](-... | null | [] | null | null | null | null | Following General Procedure D, ethyl 6-(4-ethyl-phenyl)-5-phenyl-1,2,4-triazine-3-carboxylate (Compound 13, 105 mg, 0.30 mmol) and crude 1-vinylpyrrolidine (Compound 38, 2 g) in CHCl3 (10 ml) were reacted to produce the title compound as a yellow solid.
Conditions: See reaction.notes.procedure_details.
Workup: were rea... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ester.Ester | Ester | C1CCNC1.c1cnncn1.c1ccccc1.c1ccccc1.c1cnncn1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | null | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccc(CC)cc2)c(-c2ccccc2)n1.CCOC(=O)c1nnc(-c2ccc(CC)cc2)c(-c2ccccc2)n1>C(Cl)(Cl)Cl>CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-cd87c93174394e969ed9ef7c43a800f7 | CCCc1ccc(-c2nnc(C(=O)OCC)nc2-c2ccccc2)cc1.CCCc1ccc(-c2nnc(C(=O)OCC)nc2-c2ccccc2)cc1>>CCCc1ccc(-c2ccc(C(=O)OCC)nc2-c2ccccc2)cc1 | C(=C)N1CCCC1.C1(=CC=CC=C1)C=1N=C(N=NC1C1=CC=C(C=C1)CCC)C(=O)OCC.C1(=CC=CC=C1)C=1N=C(N=NC1C1=CC=C(C=C1)CCC)C(=O)OCC.C(=C)N1CCCC1>>C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OCC)C1=CC=C(C=C1)CCC | CCCc1ccc(-[c:9]2nnc(C(=O)OCC)n[c:10]2-c2ccccc2)cc1.n1n[c:11]([C:12](=[O:13])[O:14][CH2:15][CH3:16])[n:17][c:18](-[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[c:8]1-[c:7]1[cH:6][cH:5][c:4]([CH2:3][CH2:2][CH3:1])[cH:26][cH:25]1>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12](=[O:13])[O:14]... | CCCc1ccc(-c2nnc(C(=O)OCC)nc2-c2ccccc2)cc1.CCCc1ccc(-c2nnc(C(=O)OCC)nc2-c2ccccc2)cc1 | CCCc1ccc(-c2ccc(C(=O)OCC)nc2-c2ccccc2)cc1 | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 15307b4243fc59c3c55c0a3c2481a190773671ebbfd60320f0f5af2fc3174896 | 24fd1d274a00b1436d72a65f7e271c768760ea40f563c2d852f3767e29b17299 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-C-c1:c:c:c(-[c;H0;D3;+0:1]2:n:n:c(-C(=O)-O-C-C):n:[c;H0;D3;+0:2]:2-c2:c:c:c:c:c:2):c:c:1.[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:11](-[c:12](:[c:13]):[c:14]):n:n:1>>[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:11](-[c:12](:[c:13]):... | null | [] | null | null | null | null | Following General Procedure D, ethyl 5-phenyl-6-(4-propyl-phenyl)-1,2,4-triazine-3-carboxylate (Compound 14), (153 mg, 0.46 mmol) and crude 1-vinylpyrrolidine (Compound 38, 2 g) in CHCl3 (10 ml) were reacted to produce the title compound as a yellow oil.
Conditions: See reaction.notes.procedure_details.
Workup: were re... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ester | c1ccccc1.c1cnncn1.c1ccccc1.c1cnncn1 | c1ccncc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | null | CCCc1ccc(-c2nnc(C(=O)OCC)nc2-c2ccccc2)cc1.CCCc1ccc(-c2nnc(C(=O)OCC)nc2-c2ccccc2)cc1>C(Cl)(Cl)Cl>CCCc1ccc(-c2ccc(C(=O)OCC)nc2-c2ccccc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-e1ca332375e44a608fce6d0a24b1e328 | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1.CCOC(=O)c1nnc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1>>CCOC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | C(=C)N1CCCC1.FC(C1=CC=C(C=C1)C1=C(N=C(N=N1)C(=O)OCC)C1=CC=CC=C1)(F)F.FC(C1=CC=C(C=C1)C1=C(N=C(N=N1)C(=O)OCC)C1=CC=CC=C1)(F)F.C(=C)N1CCCC1>>C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OCC)C1=CC=C(C=C1)C(F)(F)F | C(N1CCCC1)=[CH2:8].CCOC(=O)[c:7]1nnc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1.n1n[c:9](-[c:10]2[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]2)[c:20](-[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[n:27][c:6]1[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH... | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1.CCOC(=O)c1nnc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | CCOC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | e9dfcd7c4eaea72cbb32ccdf8b372fa29303834ed6ac6018661ae51fed4a4375 | 3edf262b85949dbd66d1bedc6bc75ff796f878143fa1d6dae97be6b12e5ca0aa | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-O-C(=O)-[c;H0;D3;+0:1]1:n:n:c(-c2:c:c:c(-C(-F)(-F)-F):c:c:2):c(-c2:c:c:c:c:c:2):n:1.[CH2;D1;+0:2]=C-N1-C-C-C-C-1.[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:11](-[c:12](:[c:13]):[c:14]):n:n:1>>[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;... | null | [] | null | null | null | null | Following General Procedure D, ethyl 6-(4-trifluoromethylphenyl)-5-phenyl-1,2,4-triazine-3-carboxylate (Compound 15), (378 mg, 1.01 mmol) and crude 1-vinylpyrrolidine (Compound 38, 780 mg) in CHCl3 (10 ml) were reacted to produce the title compound as a yellow oil.
Conditions: See reaction.notes.procedure_details.
Work... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Trifluoro group.Ester.Ester | Ester | C1CCNC1.c1cnncn1.c1ccccc1.c1ccccc1.c1cnncn1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HF | C(Cl)(Cl)Cl | null | null | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1.CCOC(=O)c1nnc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1>C(Cl)(Cl)Cl>CCOC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d5e75070b7ad48b4b69add6eef67c8a6 | CCOC(=O)c1nnc(-c2ccc(CC)cc2)c(-c2ccccc2)n1.CCOC(=O)c1nnc(-c2ccc(CC)cc2)c(-c2ccccc2)n1>>CCOC(=O)c1nc(-c2ccccc2)c(-c2ccc(CC)cc2)cc1C | C(=CC)N1CCCC1.C(C)C1=CC=C(C=C1)C1=C(N=C(N=N1)C(=O)OCC)C1=CC=CC=C1.C(C)C1=CC=C(C=C1)C1=C(N=C(N=N1)C(=O)OCC)C1=CC=CC=C1.C(=CC)N1CCCC1>>C(C)C1=CC=C(C=C1)C=1C=C(C(=NC1C1=CC=CC=C1)C(=O)OCC)C | n1n[c:15](-[c:16]2[cH:17][cH:18][c:19]([CH2:20][CH3:21])[cH:22][cH:23]2)[c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[n:7][c:6]1[C:4]([O:3][CH2:2][CH3:1])=[O:5].CCO[C:26](=O)[c:25]1nnc(-c2ccc(CC)cc2)c(-c2ccccc2)n1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15](... | CCOC(=O)c1nnc(-c2ccc(CC)cc2)c(-c2ccccc2)n1.CCOC(=O)c1nnc(-c2ccc(CC)cc2)c(-c2ccccc2)n1 | CCOC(=O)c1nc(-c2ccccc2)c(-c2ccc(CC)cc2)cc1C | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 15307b4243fc59c3c55c0a3c2481a190773671ebbfd60320f0f5af2fc3174896 | 24fd1d274a00b1436d72a65f7e271c768760ea40f563c2d852f3767e29b17299 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:n:n:c(-c2:c:c:c(-C-C):c:c:2):c(-c2:c:c:c:c:c:2):n:1.[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:11](-[c:12](:[c:13]):[c:14]):n:n:1>>[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:11](-[c:12](:[c:13]):... | null | [] | null | null | null | null | Following General Procedure D, ethyl 6-(4-ethylphenyl)-5-phenyl-1,2,4-triazine-3-carboxylate (Compound 13, 200 mg, 0.60 mmol) and crude 1-propenyl-pyrrolidine (Compound 39, 2 g) in CHCl3 (10 ml) were reacted to produce the title compound as a yellow oil.
Conditions: See reaction.notes.procedure_details.
Workup: were re... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ester | c1cnncn1.c1cnncn1.c1ccccc1.c1ccccc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | null | CCOC(=O)c1nnc(-c2ccc(CC)cc2)c(-c2ccccc2)n1.CCOC(=O)c1nnc(-c2ccc(CC)cc2)c(-c2ccccc2)n1>C(Cl)(Cl)Cl>CCOC(=O)c1nc(-c2ccccc2)c(-c2ccc(CC)cc2)cc1C |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2411d3daac3b49a7a31ba7c021abc1c4 | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(C)cc2)n1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(C)cc2)n1>>CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C)cc2)n1 | C(=C)N1CCCC1.C1(=CC=CC=C1)C1=C(N=C(N=N1)C(=O)OCC)C1=CC=C(C=C1)C.C1(=CC=CC=C1)C1=C(N=C(N=N1)C(=O)OCC)C1=CC=C(C=C1)C.C(=C)N1CCCC1>>C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=C(C=C1)C)C(=O)OCC | C(N1CCCC1)=[CH2:8].CCOC(=O)[c:7]1nnc(-c2ccccc2)c(-c2ccc(C)cc2)n1.n1n[c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][c:20]([CH3:21])[cH:22][cH:23]2)[n:24][c:6]1[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][c... | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(C)cc2)n1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(C)cc2)n1 | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C)cc2)n1 | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | cc03cad530703fa23e2ff0c67e0b9f19978525eb16d0ce01e888c853e60d70ca | c44d9ef0146168ac01b86e0d21b2b8ec8b64b9feba9682f4fc6d6e96c9b2417f | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-O-C(=O)-[c;H0;D3;+0:1]1:n:n:c(-c2:c:c:c:c:c:2):c(-c2:c:c:c(-C):c:c:2):n:1.[CH2;D1;+0:2]=C-N1-C-C-C-C-1.[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:11](-[c:12](:[c:13]):[c:14]):n:n:1>>[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:11](-[c... | null | [] | null | null | null | null | Following General Procedure D, ethyl 6-phenyl-5-p-tolyl-1,2,4-triazine-3-carboxylate (Compound 17, 361 mg, 1.13 mmol) and crude 1-vinylpyrrolidine (Compound 38, 806 mg) in CHCl3 (10 ml) were reacted to produce the title compound as a yellow oil.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ester.Ester | Ester | C1CCNC1.c1cnncn1.c1ccccc1.c1ccccc1.c1cnncn1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | null | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(C)cc2)n1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(C)cc2)n1>C(Cl)(Cl)Cl>CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C)cc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-562ae536f62e4b34b4aefe73e07bb20a | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(CC)cc2)n1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(CC)cc2)n1>>CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccc(CC)cc2)n1 | C(=C)N1CCCC1.C(C)C1=CC=C(C=C1)C=1N=C(N=NC1C1=CC=CC=C1)C(=O)OCC.C(C)C1=CC=C(C=C1)C=1N=C(N=NC1C1=CC=CC=C1)C(=O)OCC.C(=C)N1CCCC1>>C(C)C1=CC=C(C=C1)C1=C(C=CC(=N1)C(=O)OCC)C1=CC=CC=C1 | C(N1CCCC1)=[CH2:8].CCOC(=O)[c:7]1nnc(-c2ccccc2)c(-c2ccc(CC)cc2)n1.n1n[c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][c:20]([CH2:21][CH3:22])[cH:23][cH:24]2)[n:25][c:6]1[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13]... | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(CC)cc2)n1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(CC)cc2)n1 | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccc(CC)cc2)n1 | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | cc03cad530703fa23e2ff0c67e0b9f19978525eb16d0ce01e888c853e60d70ca | c44d9ef0146168ac01b86e0d21b2b8ec8b64b9feba9682f4fc6d6e96c9b2417f | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-O-C(=O)-[c;H0;D3;+0:1]1:n:n:c(-c2:c:c:c:c:c:2):c(-c2:c:c:c(-C-C):c:c:2):n:1.[CH2;D1;+0:2]=C-N1-C-C-C-C-1.[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:11](-[c:12](:[c:13]):[c:14]):n:n:1>>[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:11](-... | null | [] | null | null | null | null | Following General Procedure D, ethyl 5-(4-ethylphenyl)-6-phenyl-1,2,4-triazine-3-carboxylate (Compound 18, 245 mg, 0.74 mmol) and crude 1-vinylpyrrolidine (Compound 38, 572 mg) in CHCl3 (10 ml) were reacted to produce the title compound as a yellow oil.
Conditions: See reaction.notes.procedure_details.
Workup: were rea... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ester.Ester | Ester | C1CCNC1.c1cnncn1.c1ccccc1.c1ccccc1.c1cnncn1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)(Cl)Cl | null | null | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(CC)cc2)n1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(CC)cc2)n1>C(Cl)(Cl)Cl>CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccc(CC)cc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-44b6bfd75d794d3281b750bfa16d6f38 | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1>>CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1 | C(=C)N1CCCC1.FC(C1=CC=C(C=C1)C=1N=C(N=NC1C1=CC=CC=C1)C(=O)OCC)(F)F.FC(C1=CC=C(C=C1)C=1N=C(N=NC1C1=CC=CC=C1)C(=O)OCC)(F)F.C(=C)N1CCCC1>>C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC | C(N1CCCC1)=[CH2:8].CCOC(=O)[c:7]1nnc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1.n1n[c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]2)[n:27][c:6]1[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH... | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1 | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1 | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | e9dfcd7c4eaea72cbb32ccdf8b372fa29303834ed6ac6018661ae51fed4a4375 | 3edf262b85949dbd66d1bedc6bc75ff796f878143fa1d6dae97be6b12e5ca0aa | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-O-C(=O)-[c;H0;D3;+0:1]1:n:n:c(-c2:c:c:c:c:c:2):c(-c2:c:c:c(-C(-F)(-F)-F):c:c:2):n:1.[CH2;D1;+0:2]=C-N1-C-C-C-C-1.[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;+0:11](-[c:12](:[c:13]):[c:14]):n:n:1>>[C:3]-[#8:4]-[C:5](=[O;D1;H0:6])-[c;H0;D3;+0:7]1:[#7;a:8]:[c:9](-[c:10]):[c;H0;D3;... | null | [] | null | null | null | null | Following General Procedure D, ethyl 5-(4-trifluoromethylphenyl)-6-phenyl-1,2,4-triazine-3-carboxylate (Compound 19, 1 g, 2.68 mmol) and crude 1-vinylpyrrolidine (Compound 38, 1.4 g) in CHCl3 (20 ml) were reacted to produce the title compound as a yellow oil.
Conditions: See reaction.notes.procedure_details.
Workup: we... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Trifluoro group.Ester.Ester | Ester | C1CCNC1.c1cnncn1.c1ccccc1.c1ccccc1.c1cnncn1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HF | C(Cl)(Cl)Cl | null | null | C=CN1CCCC1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1.CCOC(=O)c1nnc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1>C(Cl)(Cl)Cl>CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c8ed5a439c8346ba9a574f8b0447231e | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1>>COC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OCC.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OCC>>C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OC | C[CH2:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[n:22]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[n:22]1 | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | COC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | null | OS(=O)(=O)O | CO.O | Miscellaneous | Transesterification | 797948efc8975454230354c6926ef43459a60311d668503c7a6b6bcdb3eafe50 | 6ad95641ddc9be155108cd2297ce15bcd8cb0ca25c68bfc4fce3cbf5009a236a | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[CH3;D1;+0:1] | null | [] | null | null | null | null | General Procedure E. A solution of ethyl 5,6-diphenylpyridine-2-carboxylate (Compound 21, 30 mg, 0.1 mmol) and conc. H2SO4 (3 drops) in MeOH (5 ml) was heated at 50° C. overnight. The mixture was diluted with water, and the products were extracted with ethyl acetate. The organic layer was washed with water and brine, a... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | Other | OS(=O)(=O)O.CO.O | null | null | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1>OS(=O)(=O)O.CO.O>COC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-3bbe9e8d5be141679a7e56b70fc93128 | CCOC(=O)c1ccc(-c2ccc(C)cc2)c(-c2ccccc2)n1>>COC(=O)c1ccc(-c2ccc(C)cc2)c(-c2ccccc2)n1 | C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OCC)C1=CC=C(C=C1)C.C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OCC)C1=CC=C(C=C1)C>>C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OC)C1=CC=C(C=C1)C | C[CH2:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH3:13])[cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n:23]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([CH3:13])[cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n... | CCOC(=O)c1ccc(-c2ccc(C)cc2)c(-c2ccccc2)n1 | COC(=O)c1ccc(-c2ccc(C)cc2)c(-c2ccccc2)n1 | null | OS(=O)(=O)O | CO | Miscellaneous | Transesterification | 797948efc8975454230354c6926ef43459a60311d668503c7a6b6bcdb3eafe50 | 6ad95641ddc9be155108cd2297ce15bcd8cb0ca25c68bfc4fce3cbf5009a236a | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[CH3;D1;+0:1] | null | [] | null | null | null | null | Following General Procedure E, ethyl 6-phenyl-5-p-tolyl-pyridine-2-carboxylate (Compound 22, 70 mg, 0.22 mmol) and conc. H2SO4 (3 drops) in MeOH (3 ml) were reacted to produce the title compound as a yellow solid.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | Other | OS(=O)(=O)O.CO | null | null | CCOC(=O)c1ccc(-c2ccc(C)cc2)c(-c2ccccc2)n1>OS(=O)(=O)O.CO>COC(=O)c1ccc(-c2ccc(C)cc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c8f862b8d57b4ed5a6bad16f2966582d | CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccccc2)n1>>CCc1ccc(-c2ccc(C(=O)OC)nc2-c2ccccc2)cc1 | C(C)C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OCC.C(C)C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OCC>>C(C)C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OC | C[CH2:14][O:13][C:11]([c:10]1[cH:9][cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:24][cH:23]2)[c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n:15]1)=[O:12]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[n:15][c:16]2-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:2... | CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccccc2)n1 | CCc1ccc(-c2ccc(C(=O)OC)nc2-c2ccccc2)cc1 | null | OS(=O)(=O)O | CO | Miscellaneous | Transesterification | 797948efc8975454230354c6926ef43459a60311d668503c7a6b6bcdb3eafe50 | 6ad95641ddc9be155108cd2297ce15bcd8cb0ca25c68bfc4fce3cbf5009a236a | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[CH3;D1;+0:1] | null | [] | null | null | null | null | Following General Procedure E, ethyl 5-(4-ethylphenyl)-6-phenylpyridine-2-carboxylate (Compound 23, 45 mg, 0.15 mmol) and conc. H2SO4 (3 drops) in MeOH (3 ml) were reacted to produce title compound as a yellow solid.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | Other | OS(=O)(=O)O.CO | null | null | CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccccc2)n1>OS(=O)(=O)O.CO>CCc1ccc(-c2ccc(C(=O)OC)nc2-c2ccccc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-096060c9f0dd4d369daa7a6032a8f907 | CCCc1ccc(-c2ccc(C(=O)OCC)nc2-c2ccccc2)cc1>>CCCc1ccc(-c2ccc(C(=O)OC)nc2-c2ccccc2)cc1 | C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OCC)C1=CC=C(C=C1)CCC.C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OCC)C1=CC=C(C=C1)CCC>>C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OC)C1=CC=C(C=C1)CCC | C[CH2:15][O:14][C:12]([c:11]1[cH:10][cH:9][c:8](-[c:7]2[cH:6][cH:5][c:4]([CH2:3][CH2:2][CH3:1])[cH:25][cH:24]2)[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:16]1)=[O:13]>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12](=[O:13])[O:14][CH3:15])[n:16][c:17]2-[c:18]2[cH:19][cH:20][cH... | CCCc1ccc(-c2ccc(C(=O)OCC)nc2-c2ccccc2)cc1 | CCCc1ccc(-c2ccc(C(=O)OC)nc2-c2ccccc2)cc1 | null | OS(=O)(=O)O | CO | Miscellaneous | Transesterification | 797948efc8975454230354c6926ef43459a60311d668503c7a6b6bcdb3eafe50 | 6ad95641ddc9be155108cd2297ce15bcd8cb0ca25c68bfc4fce3cbf5009a236a | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[CH3;D1;+0:1] | null | [] | null | null | null | null | Following General Procedure E, ethyl 6-phenyl-5-(4-propylphenyl)-pyridine-2-carboxylate (Compound 24, 67 mg, 0.19 mmol) and conc. H2SO4 (3 drops) in MeOH (3 ml) were reacted to produce the title compound as a white solid.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | Other | OS(=O)(=O)O.CO | null | null | CCCc1ccc(-c2ccc(C(=O)OCC)nc2-c2ccccc2)cc1>OS(=O)(=O)O.CO>CCCc1ccc(-c2ccc(C(=O)OC)nc2-c2ccccc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-c1134c48fb9443239d86e6435989bfb3 | CCOC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1>>COC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OCC)C1=CC=C(C=C1)C(F)(F)F.C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OCC)C1=CC=C(C=C1)C(F)(F)F>>C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OC)C1=CC=C(C=C1)C(F)(F)F | C[CH2:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2)[c:19](-[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[n:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2)[c:19](-[c:20]... | CCOC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | COC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | null | OS(=O)(=O)O | CO | Miscellaneous | Transesterification | 797948efc8975454230354c6926ef43459a60311d668503c7a6b6bcdb3eafe50 | 6ad95641ddc9be155108cd2297ce15bcd8cb0ca25c68bfc4fce3cbf5009a236a | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[CH3;D1;+0:1] | null | [] | null | null | null | null | Following General Procedure E, ethyl 6-phenyl-5-(4-trifluoromethylphenyl)-pyridine-2-carboxylate (Compound 25, 110 mg, 0.29 mmol) and conc. H2SO4 (5 drops) in MeOH (5 ml) were reacted to produce the title compound as a white solid.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | Other | OS(=O)(=O)O.CO | null | null | CCOC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1>OS(=O)(=O)O.CO>COC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-3748fd020f36428fb4e075cc855cf526 | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1>>COC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1 | C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC>>C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=C(C=C1)C(F)(F)F)C(=O)OC | C[CH2:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]2)[n:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][c:19]([C:20](... | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1 | COC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1 | null | OS(=O)(=O)O | CO | Miscellaneous | Transesterification | 797948efc8975454230354c6926ef43459a60311d668503c7a6b6bcdb3eafe50 | 6ad95641ddc9be155108cd2297ce15bcd8cb0ca25c68bfc4fce3cbf5009a236a | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[CH3;D1;+0:1] | null | [] | null | null | null | null | Following General Procedure E, ethyl 5-phenyl-6-(4-trifluoromethylphenyl)-pyridine-2-carboxylate (Compound 29, 103 mg, 0.28 mmol) and conc. H2SO4 (5 drops) in MeOH (5 ml) were reacted to produce the title compound as a white solid.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | Other | OS(=O)(=O)O.CO | null | null | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1>OS(=O)(=O)O.CO>COC(=O)c1ccc(-c2ccccc2)c(-c2ccc(C(F)(F)F)cc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ad10b7d5192549c796b757eb7bdd7792 | CCOC(=O)c1nc(-c2ccccc2)c(-c2ccc(CC)cc2)cc1C>>CCc1ccc(-c2cc(C)c(C(=O)OC)nc2-c2ccccc2)cc1 | C(C)C1=CC=C(C=C1)C=1C=C(C(=NC1C1=CC=CC=C1)C(=O)OCC)C.C(C)C1=CC=C(C=C1)C=1C=C(C(=NC1C1=CC=CC=C1)C(=O)OCC)C>>C(C)C1=CC=C(C=C1)C=1C=C(C(=NC1C1=CC=CC=C1)C(=O)OC)C | C[CH2:15][O:14][C:12]([c:11]1[c:9]([CH3:10])[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:25][cH:24]2)[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:16]1)=[O:13]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH3:10])[c:11]([C:12](=[O:13])[O:14][CH3:15])[n:16][c:17]2-[c:18]2[cH:19][cH:20][... | CCOC(=O)c1nc(-c2ccccc2)c(-c2ccc(CC)cc2)cc1C | CCc1ccc(-c2cc(C)c(C(=O)OC)nc2-c2ccccc2)cc1 | null | OS(=O)(=O)O | CO | Miscellaneous | Transesterification | 797948efc8975454230354c6926ef43459a60311d668503c7a6b6bcdb3eafe50 | 6ad95641ddc9be155108cd2297ce15bcd8cb0ca25c68bfc4fce3cbf5009a236a | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[CH3;D1;+0:1] | null | [] | null | null | null | null | Following General Procedure E, ethyl 5-(4-ethylphenyl)-3-methyl-6-phenylpyridine-2-carboxylate (Compound 26, 29 mg, 0.08 mmol) and conc. H2SO4 (3 drops) in MeOH (5 ml) were reacted to produce the title compound as an oil.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | Other | OS(=O)(=O)O.CO | null | null | CCOC(=O)c1nc(-c2ccccc2)c(-c2ccc(CC)cc2)cc1C>OS(=O)(=O)O.CO>CCc1ccc(-c2cc(C)c(C(=O)OC)nc2-c2ccccc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-cf4765e907dc45d8ae8032e5ff92a776 | CCc1ccc(C=CC(=O)O)cc1>>CCc1ccc(/C=C/CO)cc1 | [BH4-].[Na+].ClC(=O)OCC.C(C)C1=CC=C(C=CC(=O)O)C=C1.C(C)N(CC)CC.Cl>>C(C)C1=CC=C(C=C1)/C=C/CO | O=[C:9]([CH:8]=[CH:7][c:6]1[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:12][cH:11]1)[OH:10]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[CH:8]/[CH2:9][OH:10])[cH:11][cH:12]1 | CCc1ccc(C=CC(=O)O)cc1 | CCc1ccc(/C=C/CO)cc1 | null | null | C1CCOC1.O | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3]=[C:4]-[c:5]>>[O;D1;H1:2]-[CH2;D2;+0:1]/[C:3]=[C:4]/[c:5] | null | [] | null | null | 30 | MINUTE | General Procedure G. A solution of ethyl chloroformate (1.1 ml, 11.4 mmol) in THF (5 ml) was added to a solution of 4-ethylcinnamic acid (2 g, 11.4 mmol) and triethylamine (1.6 ml, 11.4 mmol) in THF (50 ml) at −5° C. to −10° C., and the solution was stirred for 30 min. The resulting white precipitate was filtered off, ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1 | Other | C1CCOC1.O | null | 0.5 | CCc1ccc(C=CC(=O)O)cc1>C1CCOC1.O>CCc1ccc(/C=C/CO)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-af09d11aafed42f59438f29d90dc1f26 | CCc1ccc(/C=C/CO)cc1>>CCc1ccc(/C=C/C=O)cc1 | C(C)C1=CC=C(C=C1)/C=C/CO.C(C(=O)Cl)(=O)Cl.CS(=O)C.C(C)N(CC)CC.C(C)C1=CC=C(C=C1)/C=C/CO>>C(C)C1=CC=C(C=C1)/C=C/C=O | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[CH:8]/[CH2:9][OH:10])[cH:11][cH:12]1>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6](/[CH:7]=[CH:8]/[CH:9]=[O:10])[cH:11][cH:12]1 | CCc1ccc(/C=C/CO)cc1 | CCc1ccc(/C=C/C=O)cc1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]/[C:3]=[C:4]/[c:5](:[c:6]):[c:7]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]/[C:3]=[C:4]/[c:5](:[c:6]):[c:7] | null | [] | null | null | 1 | HOUR | General Procedure H. To a solution of oxalyl chloride (5.9 ml, 11.8 mmol, 2 M in CH2Cl2) in CH2Cl2 (20 ml) was added a solution of DMSO (1.1 ml, 15.7 mmol) in CH2Cl2 (3 ml) dropwise at −60° C. A solution of (E)-3-(4-ethylphenyl)prop-2-en-1-ol (Compound 40, 1.3 g, 7.8 mmol) in CH2Cl2 (5 ml) was cannulated slowly into th... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | C(Cl)Cl | null | 1 | CCc1ccc(/C=C/CO)cc1>C(Cl)Cl>CCc1ccc(/C=C/C=O)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-ff46d30221ab41f09c751f2de95c3f11 | Cc1ccc(/C=C/CO)cc1>>Cc1ccc(/C=C/C=O)cc1 | CC1=CC=C(C=C1)/C=C/CO.C(C(=O)Cl)(=O)Cl.CS(=O)C.C(C)N(CC)CC.CC1=CC=C(C=C1)/C=C/CO>>CC1=CC=C(C=C1)/C=C/C=O | [CH3:1][c:2]1[cH:3][cH:4][c:5](/[CH:6]=[CH:7]/[CH2:8][OH:9])[cH:10][cH:11]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](/[CH:6]=[CH:7]/[CH:8]=[O:9])[cH:10][cH:11]1 | Cc1ccc(/C=C/CO)cc1 | Cc1ccc(/C=C/C=O)cc1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]/[C:3]=[C:4]/[c:5](:[c:6]):[c:7]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]/[C:3]=[C:4]/[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | Following General Procedure H, oxalyl chloride (7.1 ml, 14.2 mmol, 2 M in CH2Cl2), DMSO (1.3 ml, 18.9 mmol), (E)-3-(4-methylphenyl)prop-2-en-1-ol (Compound 41, 1.4 g, 9.5 mmol) and triethylamine (4.4 ml, 31.4 mmol) in CH2Cl2 (5 ml) were reacted to obtain the title compound as an oil.
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | C(Cl)Cl | null | null | Cc1ccc(/C=C/CO)cc1>C(Cl)Cl>Cc1ccc(/C=C/C=O)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-b4766f87ad664e35965873e1b072eb02 | CCOC(=O)CN=[N+]=[N-].Cc1ccc(/C=C/C=O)cc1>>CCOC(=O)/C(=C/C=C/c1ccc(C)cc1)N=[N+]=[N-] | CC[O-].[Na+].CC1=CC=C(C=C1)/C=C/C=O.CC1=CC=C(C=C1)/C=C/C=O.N(=[N+]=[N-])CC(=O)OCC>>N(=[N+]=[N-])\C(\C(=O)OCC)=C/C=C/C1=CC=C(C=C1)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:17]=[N+:18]=[N-:19].O=[CH:7]/[CH:8]=[CH:9]/[c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])/[C:6](=[CH:7]/[CH:8]=[CH:9]/[c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]1)[N:17]=[N+:18]=[N-:19] | CCOC(=O)CN=[N+]=[N-].Cc1ccc(/C=C/C=O)cc1 | CCOC(=O)/C(=C/C=C/c1ccc(C)cc1)N=[N+]=[N-] | null | null | CCO.C(C)O | C-C Coupling | Aldol condensation | 96b579ff44c0fff4089c750910104cf990e0a287e373b67fd8e70fc60e740467 | 5d53f2f0eebc91d0a27a3fff71d2085564fbedea85248d599c79f507c8d10a9e | c1ccccc1 | O=[CH;D2;+0:1]/[C:2]=[C:3]/[c:4](:[c:5]):[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[#7:12]=[#7;+:13]=[N;-;D1;H0:14]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])/[C;H0;D3;+0:11](-[#7:12]=[#7;+:13]=[N;-;D1;H0:14])=[CH;D2;+0:1]/[C:2]=[C:3]/[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | Following General Procedure I, a 1.38 M solution of NaOEt in ethanol (30 ml), (E)-3-(4-methylphenyl)acrylaldehyde (Compound 43, 1.1 g, 7.5 mmol) and ethyl azidoacetate (12 ml, 37.5 mmol) in EtOH (20 ml) were reacted to produce the title compound as a solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester | Ester.Conjugated diene | null | null | c1ccccc1 | HO- | CCO.C(C)O | null | null | CCOC(=O)CN=[N+]=[N-].Cc1ccc(/C=C/C=O)cc1>CCO.C(C)O>CCOC(=O)/C(=C/C=C/c1ccc(C)cc1)N=[N+]=[N-] |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-a6ee2b9eb8ae41b1997326c72ac4001b | CCOC(=O)/C(=C/C=C/c1ccc(CC)cc1)N=[N+]=[N-].c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CCOC(=O)C(=CC=Cc1ccc(CC)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=[N+]=[N-])\C(\C(=O)OCC)=C/C=C/C1=CC=C(C=C1)CC.N(=[N+]=[N-])\C(\C(=O)OCC)=C/C=C/C1=CC=C(C=C1)CC>>C(C)OC(=O)C(N=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=CC=CC1=CC=C(C=C1)CC | [N-]=[N+]=[N:18]/[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:7]\[CH:8]=[CH:9]\[c:10]1[cH:11][cH:12][c:13]([CH2:14][CH3:15])[cH:16][cH:17]1.[P:19]([c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1)([c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1)[c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[... | CCOC(=O)/C(=C/C=C/c1ccc(CC)cc1)N=[N+]=[N-].c1ccc(P(c2ccccc2)c2ccccc2)cc1 | CCOC(=O)C(=CC=Cc1ccc(CC)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | C(C)OCC | Miscellaneous | OtherReaction | ccc2663030541127fcaca4e5acedd9f2784c38c6800cb643e7bb4815d3139521 | fbd691a01e95e68b66bf8b0666f72e0c6d7102c3827b8153721b6e3b4f7ca6d9 | C(C=Cc1ccccc1)=CN=P(c1ccccc1)(c1ccccc1)c1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])/[C:5](=[C:6]/[C:7]=[C:8]/[c:9])-[N;H0;D2;+0:10]=[N+]=[N-].[c:11]:[c:12](-[P;H0;D3;+0:13](-[c:14](:[c:15]):[c:16])-[c:17](:[c:18]):[c:19]):[c:20]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](=[C:6]-[C:7]=[C:8]-[c:9])-[N;H0;D2;+0:10]=[P;H0;D4;+0:13](-[c:12](:[c:11]):[c:20])(-[c:14](:[c:15]):[c... | null | [] | null | null | 12 | HOUR | General Procedure J. A solution of triphenylphosphine (1.2 g, 4.54 mmol) in diethyl ether (10 ml) was added dropwise to a solution of ethyl (2Z,4E)-2-azido-5-(4-ethylphenyl)penta-2,4-dienoate (Compound 44, 1.2 g, 4.54 mmol) in diethyl ether (20 ml) at 0° C. The solution was stirred for 12 hours at room temperature. Eva... | 10.6084/m9.figshare.5104873.v1 | null | Azide | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)OCC | null | 12 | CCOC(=O)/C(=C/C=C/c1ccc(CC)cc1)N=[N+]=[N-].c1ccc(P(c2ccccc2)c2ccccc2)cc1>C(C)OCC>CCOC(=O)C(=CC=Cc1ccc(CC)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6b70e7d8fcb74f30a6fe09540ac7d36f | CCOC(=O)/C(=C/C=C/c1ccc(C)cc1)N=[N+]=[N-].c1ccc(P(c2ccccc2)c2ccccc2)cc1>>CCOC(=O)C(=CC=Cc1ccc(C)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=[N+]=[N-])\C(\C(=O)OCC)=C/C=C/C1=CC=C(C=C1)C>>C(C)OC(=O)C(N=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=CC=CC1=CC=C(C=C1)C | [N-]=[N+]=[N:17]/[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:7]\[CH:8]=[CH:9]\[c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]1.[P:18]([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)([c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1)[c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][CH... | CCOC(=O)/C(=C/C=C/c1ccc(C)cc1)N=[N+]=[N-].c1ccc(P(c2ccccc2)c2ccccc2)cc1 | CCOC(=O)C(=CC=Cc1ccc(C)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | C(C)OCC | Miscellaneous | OtherReaction | ccc2663030541127fcaca4e5acedd9f2784c38c6800cb643e7bb4815d3139521 | fbd691a01e95e68b66bf8b0666f72e0c6d7102c3827b8153721b6e3b4f7ca6d9 | C(C=Cc1ccccc1)=CN=P(c1ccccc1)(c1ccccc1)c1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])/[C:5](=[C:6]/[C:7]=[C:8]/[c:9])-[N;H0;D2;+0:10]=[N+]=[N-].[c:11]:[c:12](-[P;H0;D3;+0:13](-[c:14](:[c:15]):[c:16])-[c:17](:[c:18]):[c:19]):[c:20]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5](=[C:6]-[C:7]=[C:8]-[c:9])-[N;H0;D2;+0:10]=[P;H0;D4;+0:13](-[c:12](:[c:11]):[c:20])(-[c:14](:[c:15]):[c... | null | [] | null | null | null | null | Following General Procedure J, triphenylphosphine (1.5 g, 5.8 mmol) ethyl (2Z,4E)-2-azido-5-(4-methylphenyl)penta-2,4-dienoate (Compound 45, 1.5 g, 5.8 mmol) in diethyl ether (50 ml) were reacted to produce the title compound as a yellow solid.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Azide | null | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | Other | C(C)OCC | null | null | CCOC(=O)/C(=C/C=C/c1ccc(C)cc1)N=[N+]=[N-].c1ccc(P(c2ccccc2)c2ccccc2)cc1>C(C)OCC>CCOC(=O)C(=CC=Cc1ccc(C)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-12e19353160e48d3b4cc4a7e27d8621c | CCOC(=O)C(=CC=Cc1ccc(CC)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccc(C(F)(F)F)cc1>>CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccc(C(F)(F)F)cc2)n1 | FC(C1=CC=C(C=O)C=C1)(F)F.C(C)OC(=O)C(N=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=CC=CC1=CC=C(C=C1)CC.C(C)OC(=O)C(N=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=CC=CC1=CC=C(C=C1)CC>>C(C)C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC | c1ccc(P(c2ccccc2)(c2ccccc2)=[N:29][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:7][CH:8]=[CH:9][c:10]2[cH:11][cH:12][c:13]([CH2:14][CH3:15])[cH:16][cH:17]2)cc1.O=[CH:18][c:19]1[cH:20][cH:21][c:22]([C:23]([F:24])([F:25])[F:26])[cH:27][cH:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][... | CCOC(=O)C(=CC=Cc1ccc(CC)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccc(C(F)(F)F)cc1 | CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccc(C(F)(F)F)cc2)n1 | null | null | C(C)#N | Miscellaneous | OtherReaction | 02f0f968b0b9e802ed3422aadb999224491a6d9de2a1d809a485b6b3f5f050b2 | 68e49bad39abe3d5621e12b41ee11e354e282b66589572f30d80e0f4c6de6ee3 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C;H0;D3;+0:11](=[CH;D2;+0:12]-[CH;D2;+0:13]=[CH;D2;+0:14]-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19])-[N;H0;D2;+0:20]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[c;H0;D3;+0:11]1:[cH;D... | null | [] | 60 | CELSIUS | null | null | General Procedure K. 4-(trifluoromethyl)benzaldehyde (153 mg, 1.88 mmol) was added to a stirred solution of 3-ethoxycarbonyl-1,1,1-triphenyl-6-(4-ethylphenyl)-2-aza-1λ5-phosphahexa-1,3,5-triene (Compound 46, 444 mg, 0.88 mmol) in dry acetonitrile (10 ml) and the solution was heated to 60° C. for 18 hours. The solution ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Conjugated diene | Ester | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | C(C)#N | 60 | null | CCOC(=O)C(=CC=Cc1ccc(CC)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccc(C(F)(F)F)cc1>C(C)#N>CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccc(C(F)(F)F)cc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-785262fa1aa54b4eaa636014f7b15a5e | CCOC(=O)C(=CC=Cc1ccc(CC)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccncc1>>CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccncc2)n1 | N1=CC=C(C=C1)C=O.C(C)OC(=O)C(N=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=CC=CC1=CC=C(C=C1)CC.C(C)OC(=O)C(N=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=CC=CC1=CC=C(C=C1)CC>>C(C)C1=CC=C(C=C1)C=1C(=NC(=CC1)C(=O)OCC)C1=CC=NC=C1 | c1ccc(P(c2ccccc2)(c2ccccc2)=[N:25][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:7][CH:8]=[CH:9][c:10]2[cH:11][cH:12][c:13]([CH2:14][CH3:15])[cH:16][cH:17]2)cc1.O=[CH:18][c:19]1[cH:20][cH:21][n:22][cH:23][cH:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([CH2:14][CH3:15])[cH:16]... | CCOC(=O)C(=CC=Cc1ccc(CC)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccncc1 | CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccncc2)n1 | null | null | C(C)#N | Miscellaneous | OtherReaction | 02f0f968b0b9e802ed3422aadb999224491a6d9de2a1d809a485b6b3f5f050b2 | 68e49bad39abe3d5621e12b41ee11e354e282b66589572f30d80e0f4c6de6ee3 | c1ccc(-c2cccnc2-c2ccncc2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[C;H0;D3;+0:12](=[CH;D2;+0:13]-[CH;D2;+0:14]=[CH;D2;+0:15]-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:19]:[c:20])-[N;H0;D2;+0:21]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[c;H0;D3;+... | null | [] | null | null | null | null | Following General Procedure K, 4-pyridinecarboxaldehyde (92 mg, 0.86 mmol) and 3-ethoxycarbonyl-1,1,1-triphenyl-6-(4-ethylphenyl)-2-aza-1λ5-phosphahexa-1,3,5-triene (Compound 46, 434 mg, 0.86 mmol) in dry acetonitrile (10 ml) were reacted to produce the title compound as a yellow solid.
Conditions: See reaction.notes.p... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Conjugated diene | Ester | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccncc1 | HO- | C(C)#N | null | null | CCOC(=O)C(=CC=Cc1ccc(CC)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccncc1>C(C)#N>CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccncc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-d60f8401e2e744eba24dc3965d488e26 | CCOC(=O)C(=CC=Cc1ccc(CC)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccccn1>>CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccccn2)n1 | N1=C(C=CC=C1)C=O.C(C)OC(=O)C(N=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=CC=CC1=CC=C(C=C1)CC.C(C)OC(=O)C(N=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)=CC=CC1=CC=C(C=C1)CC>>C(C)C1=CC=C(C=C1)C=1C(=NC(=CC1)C(=O)OCC)C1=NC=CC=C1 | c1ccc(P(c2ccccc2)(c2ccccc2)=[N:25][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:7][CH:8]=[CH:9][c:10]2[cH:11][cH:12][c:13]([CH2:14][CH3:15])[cH:16][cH:17]2)cc1.O=[CH:18][c:19]1[cH:20][cH:21][cH:22][cH:23][n:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([CH2:14][CH3:15])[cH:16]... | CCOC(=O)C(=CC=Cc1ccc(CC)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccccn1 | CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccccn2)n1 | null | null | C(C)#N | Miscellaneous | OtherReaction | 02f0f968b0b9e802ed3422aadb999224491a6d9de2a1d809a485b6b3f5f050b2 | 68e49bad39abe3d5621e12b41ee11e354e282b66589572f30d80e0f4c6de6ee3 | c1ccc(-c2cccnc2-c2ccccn2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[#7;a:3]:[c:4]):[c:5]:[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C;H0;D3;+0:11](=[CH;D2;+0:12]-[CH;D2;+0:13]=[CH;D2;+0:14]-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19])-[N;H0;D2;+0:20]=P(-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[c;H0;D3;+0:11]1:[c... | null | [] | null | null | null | null | Following General Procedure K, 2-pyridinecarboxaldehyde (41 mg, 0.38 mmol) and 3-ethoxycarbonyl-1,1,1-triphenyl-6-(4-ethylphenyl)-2-aza-1λ5-phosphahexa-1,3,5-triene (Compound 46, 193 mg, 0.38 mmol) in dry acetonitrile (5 ml) were reacted to produce the title compound as a yellow solid.
Conditions: See reaction.notes.pr... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Conjugated diene | Ester | c1ccccc1.c1ccccc1.c1ccccc1 | c1ccncc1 | c1ccncc1.c1ccccc1.c1ccncc1 | HO- | C(C)#N | null | null | CCOC(=O)C(=CC=Cc1ccc(CC)cc1)N=P(c1ccccc1)(c1ccccc1)c1ccccc1.O=Cc1ccccn1>C(C)#N>CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccccn2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-2678073f777c403da66620f9ff443181 | CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccc(C(F)(F)F)cc2)n1>>CCc1ccc(-c2ccc(C(=O)OC)nc2-c2ccc(C(F)(F)F)cc2)cc1 | C(C)C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC.C(C)C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=C(C=C1)C(F)(F)F)C(=O)OCC>>C(C)C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=C(C=C1)C(F)(F)F)C(=O)OC | C[CH2:14][O:13][C:11]([c:10]1[cH:9][cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:28][cH:27]2)[c:16](-[c:17]2[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]2)[n:15]1)=[O:12]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[n:15][c:16]2-[c:17]2[cH:... | CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccc(C(F)(F)F)cc2)n1 | CCc1ccc(-c2ccc(C(=O)OC)nc2-c2ccc(C(F)(F)F)cc2)cc1 | null | OS(=O)(=O)O | CO | Miscellaneous | Transesterification | 797948efc8975454230354c6926ef43459a60311d668503c7a6b6bcdb3eafe50 | 6ad95641ddc9be155108cd2297ce15bcd8cb0ca25c68bfc4fce3cbf5009a236a | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[CH3;D1;+0:1] | null | [] | null | null | null | null | Following General Procedure E, ethyl 5-(4-ethylphenyl)-6-(4-(trifluoromethyl)phenyl)pyridine-2-carboxylate (Compound 48, 60 mg, 0.15 mmol) and conc. H2SO4 (10 drops) in methanol were reacted to produce the title compound as a light yellow solid.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | Other | OS(=O)(=O)O.CO | null | null | CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccc(C(F)(F)F)cc2)n1>OS(=O)(=O)O.CO>CCc1ccc(-c2ccc(C(=O)OC)nc2-c2ccc(C(F)(F)F)cc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-36fda2b6e6234cea9f29b13440c68cbc | CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccncc2)n1>>CCc1ccc(-c2ccc(C(=O)OC)nc2-c2ccncc2)cc1 | N1=C(C=CC=C1)C(=O)[O-].C(C)C1=CC=C(C=C1)C=1C(=NC(=CC1)C(=O)OCC)C1=CC=NC=C1>>C(C)C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=NC=C1)C(=O)OC | C[CH2:14][O:13][C:11]([c:10]1[cH:9][cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:24][cH:23]2)[c:16](-[c:17]2[cH:18][cH:19][n:20][cH:21][cH:22]2)[n:15]1)=[O:12]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[n:15][c:16]2-[c:17]2[cH:18][cH:19][n:20][cH:21][cH:22]... | CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccncc2)n1 | CCc1ccc(-c2ccc(C(=O)OC)nc2-c2ccncc2)cc1 | null | OS(=O)(=O)O | CO | Miscellaneous | Transesterification | 797948efc8975454230354c6926ef43459a60311d668503c7a6b6bcdb3eafe50 | 6ad95641ddc9be155108cd2297ce15bcd8cb0ca25c68bfc4fce3cbf5009a236a | c1ccc(-c2cccnc2-c2ccncc2)cc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[CH3;D1;+0:1] | null | [] | null | null | null | null | Following General Procedure E, ethyl 5-(4-ethylphenyl)-6-(pyridine-4-yl)phenyl)pyridine-2-carboxylate (Compound 49, 48 mg, 0.14 mmol) and conc. H2SO4 (10 drops) in methanol were reacted to produce the title compound as a light yellow solid.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1.c1ccncc1.c1ccncc1 | Other | OS(=O)(=O)O.CO | null | null | CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccncc2)n1>OS(=O)(=O)O.CO>CCc1ccc(-c2ccc(C(=O)OC)nc2-c2ccncc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f84eb07691ad48848f4d45b22cacaa43 | CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccccn2)n1>>CCc1ccc(-c2ccc(C(=O)OC)nc2-c2ccccn2)cc1 | N1=C(C=CC=C1)C(=O)[O-].C(C)C1=CC=C(C=C1)C=1C(=NC(=CC1)C(=O)OCC)C1=NC=CC=C1>>C(C)C1=CC=C(C=C1)C=1C=CC(=NC1C1=NC=CC=C1)C(=O)OC | C[CH2:14][O:13][C:11]([c:10]1[cH:9][cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([CH2:2][CH3:1])[cH:24][cH:23]2)[c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][n:22]2)[n:15]1)=[O:12]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11](=[O:12])[O:13][CH3:14])[n:15][c:16]2-[c:17]2[cH:18][cH:19][cH:20][cH:21][n:22]... | CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccccn2)n1 | CCc1ccc(-c2ccc(C(=O)OC)nc2-c2ccccn2)cc1 | null | OS(=O)(=O)O | CO | Miscellaneous | Transesterification | 797948efc8975454230354c6926ef43459a60311d668503c7a6b6bcdb3eafe50 | 6ad95641ddc9be155108cd2297ce15bcd8cb0ca25c68bfc4fce3cbf5009a236a | c1ccc(-c2cccnc2-c2ccccn2)cc1 | C-[CH2;D2;+0:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]-[C:3](=[O;D1;H0:4])-[#8:2]-[CH3;D1;+0:1] | null | [] | null | null | null | null | Following General Procedure E, ethyl 5-(4-ethylphenyl)-6-(pyridine-2-yl)phenyl)pyridine-2-carboxylate (Compound 50, 16 mg, 0.05 mmol) and conc. H2SO4 (10 drops) in methanol were reacted to produce the title compound as a light yellow solid.
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester | null | null | c1ccccc1.c1ccncc1.c1ccncc1 | Other | OS(=O)(=O)O.CO | null | null | CCOC(=O)c1ccc(-c2ccc(CC)cc2)c(-c2ccccn2)n1>OS(=O)(=O)O.CO>CCc1ccc(-c2ccc(C(=O)OC)nc2-c2ccccn2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-f2ac45d32fa641e1bc045452d34d6cd4 | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1>>O=Cc1ccc(-c2ccccc2)c(-c2ccccc2)n1 | C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OCC.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C(=O)OCC.CC(C)C[AlH]CC(C)C>>C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C=O | CCO[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[n:20]1 | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1 | O=Cc1ccc(-c2ccccc2)c(-c2ccccc2)n1 | null | null | C(Cl)Cl | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | 1 | HOUR | General Procedure L. To a solution of ethyl 5,6-diphenylpyridine-2-carboxylate (Compound 21, 145 mg, 0.48 mmol) in CH2Cl2 (5 ml) at −78° C. was added DIBAL-H (0.72 ml, 0.72 mmol, 1.0 M in Toluene) and the mixture was stirred between −78° C. and −60° C. for 1 hour under argon. The reaction was quenched with aq, NH4Cl, d... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | 1 | CCOC(=O)c1ccc(-c2ccccc2)c(-c2ccccc2)n1>C(Cl)Cl>O=Cc1ccc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-25cfcf96b25d4fc6b54c9b584a00826c | CCOC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1>>O=Cc1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OCC)C1=CC=C(C=C1)C(F)(F)F.C1(=CC=CC=C1)C1=C(C=CC(=N1)C(=O)OCC)C1=CC=C(C=C1)C(F)(F)F.CC(C)C[AlH]CC(C)C>>FC(C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=CC=C1)C=O)(F)F | CCO[C:2](=[O:1])[c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24]1>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:2... | CCOC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | O=Cc1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | null | null | C(Cl)Cl | Reduction | OtherReaction | ec1c6c64dd9be73981e5a6c952ab740869d298b20e87e097e88e1179cc5bc6dc | 33ddc7b9457742ba0a376f08a972e4f33779267f6f1fe15e3be786427ae9f4ec | c1ccc(-c2cccnc2-c2ccccc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;D1;H0:2]=[CH;D2;+0:1]-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | Following General Procedure L, ethyl 5-(4-trifluoromethylphenyl)-6-phenylpyridine-2-carboxylate (Compound 25, 74 mg, 0.20 mmol) and DIBAL-H (0.3 ml, 0.30 mmol, 1.0 M in hexane) in CH2Cl2 (3 ml) were reacted to produce the title compound after purification by column chromatography (silica gel, 15% ethyl acetate in hexan... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aldehyde | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | HO- | C(Cl)Cl | null | null | CCOC(=O)c1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1>C(Cl)Cl>O=Cc1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-eb6ca69b6c7b4a888c638ddbdf043103 | NCCCP(=O)(O)O.O=Cc1ccc(-c2ccccc2)c(-c2ccccc2)n1>>O=P(O)(O)CCCNCc1ccc(-c2ccccc2)c(-c2ccccc2)n1 | C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C=O.C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)C=O.NCCCP(O)(O)=O.[BH3-]C#N.[Na+]>>C1(=CC=CC=C1)C=1C=CC(=NC1C1=CC=CC=C1)CNCCCP(O)(O)=O | [O:1]=[P:2]([OH:3])([OH:4])[CH2:5][CH2:6][CH2:7][NH2:8].O=[CH:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20](-[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[n:27]1>>[O:1]=[P:2]([OH:3])([OH:4])[CH2:5][CH2:6][CH2:7][NH:8][CH2:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:... | NCCCP(=O)(O)O.O=Cc1ccc(-c2ccccc2)c(-c2ccccc2)n1 | O=P(O)(O)CCCNCc1ccc(-c2ccccc2)c(-c2ccccc2)n1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | 50 | CELSIUS | 30 | MINUTE | General Procedure M. To a solution of 5,6-diphenylpyridine-2-carbaldehyde (Compound 54, 95 mg, 0.37 mmol) and (3-amino-propyl)-phosphonic acid (51 mg, 0.37 mmol) in MeOH (3 ml) was added Bu4NOH (0.4 ml, 0.37 mmol, 1M in MeOH) under argon. The mixture was stirred at 50° C. for 30 min. before adding NaCNBH3 (23 mg, 0.37 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | Other | CO | 50 | 0.5 | NCCCP(=O)(O)O.O=Cc1ccc(-c2ccccc2)c(-c2ccccc2)n1>CO>O=P(O)(O)CCCNCc1ccc(-c2ccccc2)c(-c2ccccc2)n1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-022616730b0b4007b11ba681d49f496b | Cc1ccc(-c2ccc(C=O)nc2-c2ccccc2)cc1.NCCCP(=O)(O)O>>Cc1ccc(-c2ccc(CNCCCP(=O)(O)O)nc2-c2ccccc2)cc1 | [BH3-]C#N.[Na+].C1(=CC=CC=C1)C1=C(C=CC(=N1)C=O)C1=CC=C(C=C1)C.C1(=CC=CC=C1)C1=C(C=CC(=N1)C=O)C1=CC=C(C=C1)C.NCCCP(O)(O)=O>>C1(=CC=CC=C1)C1=C(C=CC(=N1)CNCCCP(O)(O)=O)C1=CC=C(C=C1)C | O=[CH:10][c:9]1[cH:8][cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:28][cH:27]2)[c:20](-[c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[n:19]1.[NH2:11][CH2:12][CH2:13][CH2:14][P:15](=[O:16])([OH:17])[OH:18]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([CH2:10][NH:11][CH2:12][CH2:13][CH2:14][P:15](=[O:16])([O... | Cc1ccc(-c2ccc(C=O)nc2-c2ccccc2)cc1.NCCCP(=O)(O)O | Cc1ccc(-c2ccc(CNCCCP(=O)(O)O)nc2-c2ccccc2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | Following General Procedure M, 6-phenyl-5-p-tolylpyridine-2-carbaldehyde (Compound 55, 67 mg, 0.25 mmol), (3-aminopropyl)-phosphonic acid (34 mg, 0.25 mmol), Bu4NOH (0.2 ml, 0.25 mmol, 1 M in MeOH) and NaCNBH3 (15 mg, 0.25 mmol) in MeOH (3 ml) were reacted to produce the title compound as a white solid.
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | Other | CO | null | null | Cc1ccc(-c2ccc(C=O)nc2-c2ccccc2)cc1.NCCCP(=O)(O)O>CO>Cc1ccc(-c2ccc(CNCCCP(=O)(O)O)nc2-c2ccccc2)cc1 |
ord_dataset-03ba810b7f464a06b5d8787af2e8b64e | ord-6c223868fa6e418e812f48b461d0ad88 | NCCCP(=O)(O)O.O=Cc1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1>>O=P(O)(O)CCCNCc1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | [BH3-]C#N.[Na+].FC(C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=CC=C1)C=O)(F)F.FC(C1=CC=C(C=C1)C=1C=CC(=NC1C1=CC=CC=C1)C=O)(F)F.NCCCP(O)(O)=O>>C1(=CC=CC=C1)C1=C(C=CC(=N1)CNCCCP(O)(O)=O)C1=CC=C(C=C1)C(F)(F)F | [O:1]=[P:2]([OH:3])([OH:4])[CH2:5][CH2:6][CH2:7][NH2:8].O=[CH:9][c:10]1[cH:11][cH:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]2)[c:24](-[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[n:31]1>>[O:1]=[P:2]([OH:3])([OH:4])[CH2:5][CH2:6][CH2:7][NH:8][CH2:9][c:10]1[cH:11][cH:12][c:13](-[c:... | NCCCP(=O)(O)O.O=Cc1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | O=P(O)(O)CCCNCc1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1ccc(-c2cccnc2-c2ccccc2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | Following General Procedure M, 5-(4-trifluoromethylphenyl)-6-phenyl-pyridine-2-carbaldehyde (Compound 57, 58 mg, 0.18 mmol), (3-amino-propyl)-phosphonic acid (25 mg, 0.18 mmol), Bu4NOH (0.18 ml, 0.18 mmol, 1 M in MeOH) and NaCNBH3 (11 mg, 0.18 mmol) in MeOH (3 ml) were reacted to produce the title compound as a white s... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1ccncc1.c1ccccc1.c1ccccc1 | Other | CO | null | null | NCCCP(=O)(O)O.O=Cc1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1>CO>O=P(O)(O)CCCNCc1ccc(-c2ccc(C(F)(F)F)cc2)c(-c2ccccc2)n1 |
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