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-c34472859da14a81bfe0f74e60f15c43 | ord-8a1a0fb0e4634cdfa19d11f0ccca9423 | [Zn+2]>>[Zn] | N[C@@H](CC(C)C)C(=O)O.O.O.C(C)(=O)[O-].[Zn+2].C(C)(=O)[O-]>>N[C@@H](CC(C)C)C(=O)O.[Zn] | [Zn+2:10]>>[Zn:10] | [Zn+2] | [Zn] | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [Zn+2;H0;D0:1]>>[Zn;H0;D0;+0:1] | null | [] | 120 | FAHRENHEIT | null | null | Anhydrous L-leucine, 5.2472 g, 0.0400 mole, was dissolved in 30 ml of deionized water and heated to 120° F. Ultra-pure zinc acetate dihydrate, Zn(C2H3O2)2.2H2O , 4.3900 g, 0.0200 mole, was added in small increments over one hour, with stirring. The solution did not clear, so another 20 ml of water was added and the mix... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | 48.888889 | null | [Zn+2]>O>[Zn] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-34394dfcaccf4a48aee186bc13d9f8b7 | C=CC(C)(CCC=C(C)C)OC(=O)c1ccccc1C(=O)OC(C)(C=C)CCC=C(C)C>>O=C(O)c1ccccc1C(=O)O | C(C=1C(C(=O)OC(C)(C=C)CCC=C(C)C)=CC=CC1)(=O)OC(C)(C=C)CCC=C(C)C>>C(C=1C(C(=O)O)=CC=CC1)(=O)O | C=CC(C)(CCC=C(C)C)[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[O:12]C(C)(C=C)CCC=C(C)C>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[OH:12] | C=CC(C)(CCC=C(C)C)OC(=O)c1ccccc1C(=O)OC(C)(C=C)CCC=C(C)C | O=C(O)c1ccccc1C(=O)O | null | [Pd] | O1CCCC1 | Deprotection | OtherReaction | 064e20395e3798bb1c3cf27f873776cf6ffc082e895c9c3227095660e44f6159 | d5dc5bf350cd31d4b8a0bfdf55368741f5e171d5fe01afbe6ebe65a5f76276a2 | c1ccccc1 | C-C(-C)=C-C-C-C(-C)(-C=C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-C(-C)(-C-C-C=C(-C)-C)-C=C>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8] | null | [] | null | null | null | null | A solution of 10 g (22.8 mmol) dilinalyl phthalate (prepared by the procedure of Example 1) in 100 mL tetrahydrofuran was treated with 2 g palladium on charcoal catalyst and hydrogenated quickly at 40 psi. A small amount of cleavage gave some phthalic acid byproduct, so the mixture was chromatographed on silica gel to ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Vinyl.Vinyl | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1 | Other | [Pd].O1CCCC1 | null | null | C=CC(C)(CCC=C(C)C)OC(=O)c1ccccc1C(=O)OC(C)(C=C)CCC=C(C)C>[Pd].O1CCCC1>O=C(O)c1ccccc1C(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-dd865e276f084759b14ff44b29b482e1 | [Fe+2]>>[Fe] | O.O.O.O.O.O.O.S(=O)(=O)([O-])[O-].[Fe+2].C(CN(CC(=O)O)CC(=O)O)N(CC(=O)O)CC(=O)O>>[Fe].C(CN(CC(=O)O)CC(=O)O)N(CC(=O)O)CC(=O)O | [Fe+2:21]>>[Fe:21] | [Fe+2] | [Fe] | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | [Fe+2;H0;D0:1]>>[Fe;H0;D0;+0:1] | null | [] | null | null | null | null | A 100X stock solution of iron and EDTA was prepared by dissolving 1.39 g of iron (II) sulfate heptahydrate and 1.86 g of disodium-EDTA in 500 ml of distilled, deionized water.
Conditions: See reaction.notes.procedure_details.
Workup: of distilled | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | [Fe+2]>>[Fe] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-23a529a4d1a3492180019eb2f35a3256 | [Cl-]>>[Cl-] | S(=O)(=O)([O-])[O-].CC[C@@]1(C[C@@H]2C[C@@](C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)[C@]78CCN9[C@H]7[C@@](C=CC9)([C@H]([C@@]([C@@H]8N6C=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O.OS(=O)(=O)O.[Cl-]>>CC[C@@]1(C[C@@H]2C[C@@](C3=C(C=4C=CC=CC4N3)CCN(C2)C1)(C=5C=C6C(=CC5OC)N([C@@H]7[C@]68CCN9[C@H]8[C@@](C=CC9)([C@H]([C@@]7(C(... | [Cl-:61]>>[Cl-:61] | [Cl-] | [Cl-] | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | null | null | null | null | The sulphate of vincristine sulphate parent substance was replaced by chloride ions. Vincristine chloride produced in this way was used for the further equilibrium studies.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | null | null | null | [Cl-]>>[Cl-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4c4b391c193843ba84207377c5f51841 | CS(=O)(=O)N1CCN(C(=O)Cl)C1=O.NC(C(=O)O)c1cscn1>>CS(=O)(=O)N1CCN(C(=O)NC(C(=O)O)c2cscn2)C1=O | [OH-].[Na+].NC(C(=O)O)C=1N=CSC1.[OH-].[Na+].O=C1N(CCN1S(=O)(=O)C)C(=O)Cl>>O=C1N(CCN1S(=O)(=O)C)C(=O)NC(C(=O)O)C=1N=CSC1 | Cl[C:9]([N:8]1[CH2:7][CH2:6][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[C:21]1=[O:22])=[O:10].[NH2:11][CH:12]([C:13](=[O:14])[OH:15])[c:16]1[cH:17][s:18][cH:19][n:20]1>>[CH3:1][S:2](=[O:3])(=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([C:9](=[O:10])[NH:11][CH:12]([C:13](=[O:14])[OH:15])[c:16]2[cH:17][s:18][cH:19][n:20]2)[C:21]1=[O:22] | CS(=O)(=O)N1CCN(C(=O)Cl)C1=O.NC(C(=O)O)c1cscn1 | CS(=O)(=O)N1CCN(C(=O)NC(C(=O)O)c2cscn2)C1=O | null | null | O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | b66f0127f31d05607e2c1652b6b4f18487a952a502aa7b80cc303d6d5e78ce9e | fae94ce6ae5856f710438d2b0c3a2fe4ce15d644f728354de0d8947852529b84 | O=C1NCCN1C(=O)NCc1cscn1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]1-[C:4]-[C:5]-[#7:6](-[#16:7])-[C:8]-1=[O;D1;H0:9].[#16;a:10]:[c:11]:[c:12](-[C:13](-[NH2;D1;+0:14])-[C:15](=[O;D1;H0:16])-[O;D1;H1:17]):[#7;a:18]>>[#16:7]-[#7:6]1-[C:5]-[C:4]-[#7:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:14]-[C:13](-[C:15](=[O;D1;H0:16])-[O;D1;H1:17])-[c:12](:[#7... | 53 | [{"value": 53.0, "product": "O=C1N(CCN1S(=O)(=O)C)C(=O)NC(C(=O)O)C=1N=CSC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | DL-2-Amino-2-(thiazol-4-yl)acetic acid (214 mg) [prepared by the method described in J. Med. Chem. 16, 978 (1973)] was taken up in water (10 ml) and the pH was adjusted to 6.5 by the addition of 2N sodium hydroxide solution. 2-Oxo-3-methylsulphonylimidazolidin-1-ylcarbonyl chloride (310 mg) was added to the stirred sol... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Substituted dicarboximide.Primary amine | Urea | null | null | C1C[NH]C[NH]1.c1cscn1 | HCl | O | null | 1 | CS(=O)(=O)N1CCN(C(=O)Cl)C1=O.NC(C(=O)O)c1cscn1>O>CS(=O)(=O)N1CCN(C(=O)NC(C(=O)O)c2cscn2)C1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-10d7e8c733bc4de0894890bb58362714 | CON=C(C(=O)O)c1csnn1>>NC(C(=O)O)c1csnn1 | CON=C(C(=O)O)C=1N=NSC1.Cl.[H][H]>>Cl.NC(C(=O)O)C=1N=NSC1 | CO[N:2]=[C:3]([C:4](=[O:5])[OH:6])[c:7]1[cH:8][s:9][n:10][n:11]1>>[NH2:2][CH:3]([C:4](=[O:5])[OH:6])[c:7]1[cH:8][s:9][n:10][n:11]1 | CON=C(C(=O)O)c1csnn1 | NC(C(=O)O)c1csnn1 | null | null | O.CO | Reduction | OtherReaction | 590afc40c548fcf8cf088b5c5eae6e6dcc5b58f23e7c043040c768ce23733c63 | f4ea0365445c3397e612b814f46606587238bdfc396964fde128f445018666fe | c1csnn1 | C-O-[N;H0;D2;+0:1]=[C;H0;D3;+0:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5])-[c:6]1:[#7;a:7]:[#7;a:8]:[#16;a:9]:[c:10]:1>>[NH2;D1;+0:1]-[CH;D3;+0:2](-[C:3](=[O;D1;H0:4])-[O;D1;H1:5])-[c:6]1:[#7;a:7]:[#7;a:8]:[#16;a:9]:[c:10]:1 | null | [] | null | null | 1 | HOUR | A solution of 2-methoxyimino-2-(1,2,3-thiadiazol-4-yl)acetic acid (mixture of syn- and anti-isomers) (500 mg) [prepared by the method described in Belgian Pat. No. 859384 (1978)] in a mixture of methanol (10 cm3) and water (2.3 cm3) was treated with 1N hydrochloric acid (2.7 cm3) and hydrogenated under 50 psi of hydrog... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary amine | null | null | c1csnn1 | Other | O.CO | null | 1 | CON=C(C(=O)O)c1csnn1>O.CO>NC(C(=O)O)c1csnn1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7117754e6e8640b49cc4ad4fb2f2ff13 | CCN1CCN(C(=O)Cl)C(=O)C1=O.NC(C(=O)O)c1csnn1>>CCN1CCN(C(=O)NC(C(=O)O)c2csnn2)C(=O)C1=O | Cl.NC(C(=O)O)C=1N=NSC1.C(C)N1C(C(N(CC1)C(=O)Cl)=O)=O>>C(C)N1C(C(N(CC1)C(=O)NC(C(=O)O)C=1N=NSC1)=O)=O | Cl[C:7]([N:6]1[CH2:5][CH2:4][N:3]([CH2:2][CH3:1])[C:21](=[O:22])[C:19]1=[O:20])=[O:8].[NH2:9][CH:10]([C:11](=[O:12])[OH:13])[c:14]1[cH:15][s:16][n:17][n:18]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([C:7](=[O:8])[NH:9][CH:10]([C:11](=[O:12])[OH:13])[c:14]2[cH:15][s:16][n:17][n:18]2)[C:19](=[O:20])[C:21]1=[O:22] | CCN1CCN(C(=O)Cl)C(=O)C1=O.NC(C(=O)O)c1csnn1 | CCN1CCN(C(=O)NC(C(=O)O)c2csnn2)C(=O)C1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | b66f0127f31d05607e2c1652b6b4f18487a952a502aa7b80cc303d6d5e78ce9e | fae94ce6ae5856f710438d2b0c3a2fe4ce15d644f728354de0d8947852529b84 | O=C1NCCN(C(=O)NCc2csnn2)C1=O | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3](-[C:4])-[C:5](=[O;D1;H0:6])-[C:7](=[O;D1;H0:8])-[#7:9].[NH2;D1;+0:10]-[C:11](-[C:12](=[O;D1;H0:13])-[O;D1;H1:14])-[c:15]1:[#7;a:16]:[#7;a:17]:[#16;a:18]:[c:19]:1>>[#7:9]-[C:7](=[O;D1;H0:8])-[C:5](=[O;D1;H0:6])-[#7:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:11](-[C:12](=[O;D... | 81.3 | [{"value": 81.3, "product": "C(C)N1C(C(N(CC1)C(=O)NC(C(=O)O)C=1N=NSC1)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound (1.24 g) was prepared from 2-amino-2-(1,2,3-thiadiazol-4-yl)acetic acid hydrochloride [Example 3(a)] (912 mg) and 4-ethyl-2,3-dioxopiperazin-1-ylcarbonyl chloride (953 mg) by the method of Example 1(a).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Substituted dicarboximide.Primary amine | Urea | null | null | C1C[NH]CC[NH]1.c1csnn1 | HCl | null | null | null | CCN1CCN(C(=O)Cl)C(=O)C1=O.NC(C(=O)O)c1csnn1>>CCN1CCN(C(=O)NC(C(=O)O)c2csnn2)C(=O)C1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-97ec024c8b84436f901f5300f799487a | Cn1nc(O)c(=O)nc1SCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1.O=Cc1ccccc1>>Cn1nc(O)c(=O)nc1SCC1=C(C(=O)O)N2C(=O)[C@@H](N=Cc3ccccc3)[C@H]2SC1 | N[C@H]1[C@@H]2N(C(=C(CS2)CSC=2N(N=C(C(N2)=O)O)C)C(=O)O)C1=O.C(C1=CC=CC=C1)=O>>C(C1=CC=CC=C1)=N[C@H]1[C@@H]2N(C(=C(CS2)CSC=2N(N=C(C(N2)=O)O)C)C(=O)O)C1=O | [CH3:1][n:2]1[n:3][c:4]([OH:5])[c:6](=[O:7])[n:8][c:9]1[S:10][CH2:11][C:12]1=[C:13]([C:14](=[O:15])[OH:16])[N:17]2[C:18](=[O:19])[C@@H:20]([NH2:21])[C@H:29]2[S:30][CH2:31]1.O=[CH:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][n:2]1[n:3][c:4]([OH:5])[c:6](=[O:7])[n:8][c:9]1[S:10][CH2:11][C:12]1=[C:13]([C:14](=[... | Cn1nc(O)c(=O)nc1SCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1.O=Cc1ccccc1 | Cn1nc(O)c(=O)nc1SCC1=C(C(=O)O)N2C(=O)[C@@H](N=Cc3ccccc3)[C@H]2SC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | Addition of primary amines to aldehydes/thiocarbonyls | d409dfd3247abb6c1b1364aec380d25720f21e374fd2124063f2d2ce54d31c4f | 9b341044a5a058244685b0b956d33f593ccdcd7346fa1d8d7b98a302fd35b8a2 | O=C1[C@@H](N=Cc2ccccc2)[C@H]2SCC(CSc3nc(=O)cn[nH]3)=CN12 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#16:5]-[C:6]1-[#7:7](-[C:8](-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])=[C:12])-[C:13](=[O;D1;H0:14])-[C:15]-1-[NH2;D1;+0:16]>>[#16:5]-[C:6]1-[#7:7](-[C:8](-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])=[C:12])-[C:13](=[O;D1;H0:14])-[C:15]-1-[N;H0;D2;+0:16]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 93.2 | [{"value": 93.2, "product": "C(C1=CC=CC=C1)=N[C@H]1[C@@H]2N(C(=C(CS2)CSC=2N(N=C(C(N2)=O)O)C)C(=O)O)C1=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 7β-amino-3-[(2,5-dihydro-6- hydroxy-2-methyl-5-oxo-1,2,4-triazin-3-yl)thiomethyl]ceph-3-em-4-carboxylic acid (see EP 65748) (3.71 g) in dimethylformamide (50 ml) was treated with benzaldehyde (4.24 g) and the mixture was sonicated in an ultrasound bath at 25° for 0.5 hours, by which time a clear solutio... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Substituted imine | null | null | c1cnncn1.C1=CN2CC[C@H]2SC1.c1ccccc1 | HO- | CN(C=O)C | null | null | Cn1nc(O)c(=O)nc1SCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1.O=Cc1ccccc1>CN(C=O)C>Cn1nc(O)c(=O)nc1SCC1=C(C(=O)O)N2C(=O)[C@@H](N=Cc3ccccc3)[C@H]2SC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-40c2694dae9c48129693b32c2ddd0de2 | O=C(O)c1cc(F)c(F)cc1Br.O=S(Cl)Cl>>O=C(Cl)c1cc(F)c(F)cc1Br | BrC1=C(C(=O)O)C=C(C(=C1)F)F.S(=O)(Cl)Cl>>BrC1=C(C(=O)Cl)C=C(C(=C1)F)F | O[C:2](=[O:1])[c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[cH:10][c:11]1[Br:12].O=S(Cl)[Cl:3]>>[O:1]=[C:2]([Cl:3])[c:4]1[cH:5][c:6]([F:7])[c:8]([F:9])[cH:10][c:11]1[Br:12] | O=C(O)c1cc(F)c(F)cc1Br.O=S(Cl)Cl | O=C(Cl)c1cc(F)c(F)cc1Br | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 1 | HOUR | Thionyl chloride (70 ml) is added to 2-bromo-4,5-difluorobenzoic acid (39.5 g), and the mixture is allowed to stand at room temperature for one hour and then refluxed for one hour. After completion of the reaction, the excess thionyl chloride is distilled off under reduced pressure. The oily residue is distilled under ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | null | null | 1 | O=C(O)c1cc(F)c(F)cc1Br.O=S(Cl)Cl>>O=C(Cl)c1cc(F)c(F)cc1Br |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-575364d959734897b000c05ed2143923 | CCOC(=O)CC(=O)OCC.O=C(Cl)c1cc(F)c(F)cc1Br>>CCOC(=O)C(C(=O)OCC)C(=O)c1cc(F)c(F)cc1Br | [Mg].BrC1=C(C(=O)Cl)C=C(C(=C1)F)F.S(O)(O)(=O)=O.C(CC(=O)OCC)(=O)OCC>>BrC1=C(C(=O)C(C(=O)OCC)C(=O)OCC)C=C(C(=C1)F)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[O:9][CH2:10][CH3:11].Cl[C:12](=[O:13])[c:14]1[cH:15][c:16]([F:17])[c:18]([F:19])[cH:20][c:21]1[Br:22]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[C:12](=[O:13])[c:14]1[cH:15][c:16]([F:17])[c:18]([F:19])[cH:20][c:21]1[Br:22] | CCOC(=O)CC(=O)OCC.O=C(Cl)c1cc(F)c(F)cc1Br | CCOC(=O)C(C(=O)OCC)C(=O)c1cc(F)c(F)cc1Br | null | null | CCOCC.C(Cl)(Cl)(Cl)Cl.C(C)O | C-C Coupling | OtherReaction | 872dd4ea89053916cf9ee557745988425973a0fb6c3fde7e681bde82864a0018 | a7050091370b27e4945622bf444949c46249e49bd26e357ae44671cc72030a02 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10](-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 108.2 | [{"value": 108.2, "product": "BrC1=C(C(=O)C(C(=O)OCC)C(=O)OCC)C=C(C(=C1)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Magnesium ribbon (7.3 g) is suspended in absolute ethanol (15 ml), and thereto is added carbon tetrachloride (1.5 ml), and thereto is added dropwise a mixture of diethyl malonate (48 g), absolute ethanol (30 ml) and anhydrous ether (120 ml) over a period of one hour. After the addition, the mixture is refluxed for 2 ho... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Ester | Ketone | null | null | c1ccccc1 | HCl | CCOCC.C(Cl)(Cl)(Cl)Cl.C(C)O | null | 8 | CCOC(=O)CC(=O)OCC.O=C(Cl)c1cc(F)c(F)cc1Br>CCOCC.C(Cl)(Cl)(Cl)Cl.C(C)O>CCOC(=O)C(C(=O)OCC)C(=O)c1cc(F)c(F)cc1Br |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b28196377e324dcfbda86271a54c7717 | CCOC(=O)C(C(=O)OCC)C(=O)c1cc(F)c(F)cc1Br>>CCOC(=O)CC(=O)c1cc(F)c(F)cc1Br | BrC1=C(C(=O)C(C(=O)OCC)C(=O)OCC)C=C(C(=C1)F)F.C1(=CC=C(C=C1)S(=O)(=O)O)C>>BrC1=C(C(=O)CC(=O)OCC)C=C(C(=C1)F)F | CCOC(=O)[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:7](=[O:8])[c:9]1[cH:10][c:11]([F:12])[c:13]([F:14])[cH:15][c:16]1[Br:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[c:9]1[cH:10][c:11]([F:12])[c:13]([F:14])[cH:15][c:16]1[Br:17] | CCOC(=O)C(C(=O)OCC)C(=O)c1cc(F)c(F)cc1Br | CCOC(=O)CC(=O)c1cc(F)c(F)cc1Br | null | null | O | Reduction | Decarboxylation | c8cf2024f85522a1f5dc304862ec185b9ba9539171a955fed5fc95020255a5b8 | 92cfcced8d7e743a323bd1528115ee07546647fe3eca55d712fbb9eefe0c9e22 | c1ccccc1 | C-C-O-C(=O)-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:6](=[O;D1;H0:7])-[c:8]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[C:6](=[O;D1;H0:7])-[c:8] | 84.9 | [{"value": 84.9, "product": "BrC1=C(C(=O)CC(=O)OCC)C=C(C(=C1)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of diethyl (2-bromo-4,5-difluorobenzoyl)malonate (75.6 g) in water (100 ml) is added p-toluenesulfonic acid (0.3 g), and the mixture is refluxed for 3 hours. After cooling, the reaction mixture is extracted with dichloromethane. The dichloromethane layer is washed with saturated aqueous sodium chloride so... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ester | Ketone | null | null | c1ccccc1 | HO- | O | null | null | CCOC(=O)C(C(=O)OCC)C(=O)c1cc(F)c(F)cc1Br>O>CCOC(=O)CC(=O)c1cc(F)c(F)cc1Br |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7af6035e622f47afb28a3eccd209e00d | CCOC(=O)CC(=O)c1cc(F)c(F)cc1Br.CCOC([O-])[O-]>>CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(F)cc1Br | BrC1=C(C(=O)CC(=O)OCC)C=C(C(=C1)F)F.C(OCC)([O-])[O-].C(C)(=O)OC(C)=O>>BrC1=C(C(=O)C(C(=O)OCC)=COCC)C=C(C(=C1)F)F | [CH2:5]([C:6](=[O:7])[O:8][CH2:9][CH3:10])[C:11](=[O:12])[c:13]1[cH:14][c:15]([F:16])[c:17]([F:18])[cH:19][c:20]1[Br:21].[O-][CH:4]([O-])[O:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][O:3][CH:4]=[C:5]([C:6](=[O:7])[O:8][CH2:9][CH3:10])[C:11](=[O:12])[c:13]1[cH:14][c:15]([F:16])[c:17]([F:18])[cH:19][c:20]1[Br:21] | CCOC(=O)CC(=O)c1cc(F)c(F)cc1Br.CCOC([O-])[O-] | CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(F)cc1Br | null | null | null | C-C Coupling | OtherReaction | 639a4ce9226015e35f6437fdf707a9468b6252f0523264bdae9fa6f28cb22374 | c4e4f7b42a406bead919c0be81d4397946ea7bc6e68a2cd47e017aa044114e5b | c1ccccc1 | [C:1]-[#8:2]-[CH;D3;+0:3](-[O-])-[O-].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11]>>[C:1]-[#8:2]-[CH;D2;+0:3]=[C;H0;D3;+0:8](-[C:9](=[O;D1;H0:10])-[c:11])-[C:6](=[O;D1;H0:7])-[#8:5]-[C:4] | 79.7 | [{"value": 79.7, "product": "BrC1=C(C(=O)C(C(=O)OCC)=COCC)C=C(C(=C1)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | A mixture of ethyl (2-bromo-4,5-difluorobenzoyl)acetate (52.0 g), ethyl orthoformate (36.6 g) and acetic anhydride (41.6 g) is heated at 150° C. for 2 hours. After the reaction, the reaction mixture is concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (solvent, d... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ether | Ketone.Ester.Ether | null | null | c1ccccc1 | HO- | null | 150 | null | CCOC(=O)CC(=O)c1cc(F)c(F)cc1Br.CCOC([O-])[O-]>>CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(F)cc1Br |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-266ae5f07b5c46bc8eea2a4cb77396f0 | CCOC(=O)C(=CN(C)C)C(=O)c1cc(F)c(F)cc1Br.COc1ccc(N)c(F)c1>>CCOC(=O)c1cn(-c2ccc(OC)cc2F)c2cc(F)c(F)cc2c1=O | BrC1=C(C(=O)C(C(=O)OCC)=CN(C)C)C=C(C(=C1)F)F.FC1=C(N)C=CC(=C1)OC>>FC=1C=C2C(C(=CN(C2=CC1F)C1=C(C=C(C=C1)OC)F)C(=O)OCC)=O | CN(C)[CH:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:26]([c:25]1[c:18](Br)[cH:19][c:20]([F:21])[c:22]([F:23])[cH:24]1)=[O:27].[NH2:8][c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][c:16]1[F:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][c:16]2[F:17])[c:18]2[... | CCOC(=O)C(=CN(C)C)C(=O)c1cc(F)c(F)cc1Br.COc1ccc(N)c(F)c1 | CCOC(=O)c1cn(-c2ccc(OC)cc2F)c2cc(F)c(F)cc2c1=O | null | null | C1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | c79d84f56965d6e61ab7d2dc666c87f6a3a16f834a7a4fa8886df2977a8c2425 | 549891eb5518f7b09df7a3ed17084097e78f66d49ed84fbe3d04e9efbf8d2578 | O=c1ccn(-c2ccccc2)c2ccccc12 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C;H0;D3;+0:7](=[CH;D2;+0:8]-N(-C)-C)-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]):[c:13].[F;D1;H0:14]-[c:15](:[c:16]):[c;H0;D3;+0:17](-[NH2;D1;+0:18]):[c:19]:[c:20]>>[C:12]-[#8:11]-[C:9](=[O;D1;H0:10])-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[n;H0;D3;+0:18](-[c;H0;D3;+0... | 52 | [{"value": 52.0, "product": "FC=1C=C2C(C(=CN(C2=CC1F)C1=C(C=C(C=C1)OC)F)C(=O)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Ethyl 2-(2-bromo-4,5-difluorobenzoyl)-3-dimethylaminoacrylate (1.09 g) and 2-fluoro-4-methoxyaniline (0.51 g) are dissolved in benzene (10 ml), and the mixture is allowed to stand at room temperature for 2 hours. The reaction mixture is washed with diluted hydrochloric acid and saturated aqueous sodium chloride, and dr... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Aromatic halide.Ketone.Ester.Primary amine | Ester | c1ccccc1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HBr | C1=CC=CC=C1 | null | 2 | CCOC(=O)C(=CN(C)C)C(=O)c1cc(F)c(F)cc1Br.COc1ccc(N)c(F)c1>C1=CC=CC=C1>CCOC(=O)c1cn(-c2ccc(OC)cc2F)c2cc(F)c(F)cc2c1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e84daf1cd4e04a29ad9f3282491f4787 | CCOC(=O)c1cn(-c2ccc(OC)cc2)c2cc(F)c(F)cc2c1=O>>COc1ccc(-n2cc(C(=O)O)c(=O)c3cc(F)c(F)cc32)cc1 | FC=1C=C2C(C(=CN(C2=CC1F)C1=CC=C(C=C1)OC)C(=O)OCC)=O.Cl>>FC=1C=C2C(C(=CN(C2=CC1F)C1=CC=C(C=C1)OC)C(=O)O)=O | CC[O:12][C:10]([c:9]1[cH:8][n:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:24][cH:23]2)[c:22]2[c:15]([c:13]1=[O:14])[cH:16][c:17]([F:18])[c:19]([F:20])[cH:21]2)=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13](=[O:14])[c:15]3[cH:16][c:17]([F:18])[c:19]([F:20])[cH:21][c:22]23)... | CCOC(=O)c1cn(-c2ccc(OC)cc2)c2cc(F)c(F)cc2c1=O | COc1ccc(-n2cc(C(=O)O)c(=O)c3cc(F)c(F)cc32)cc1 | null | null | C(C)(=O)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccn(-c2ccccc2)c2ccccc12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 96 | [{"value": 96.0, "product": "FC=1C=C2C(C(=CN(C2=CC1F)C1=CC=C(C=C1)OC)C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 2 | HOUR | To ethyl 6,7-difluoro-1-(4 -methoxyphenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.61 g) are added 90% acetic acid (8.0 ml) and conc. hydrochloric acid (2.0 ml), and the mixture is heated with stirring at 110° C. for 2 hours. After the reaction, the solvent is distilled off under reduced pressure. The resulting res... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2ncccc2c1 | Other | C(C)(=O)O | 110 | 2 | CCOC(=O)c1cn(-c2ccc(OC)cc2)c2cc(F)c(F)cc2c1=O>C(C)(=O)O>COc1ccc(-n2cc(C(=O)O)c(=O)c3cc(F)c(F)cc32)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-64c09d7bf10743029fcdc8099b159fc4 | CCOC(=O)c1cn(-c2ccc(OC)cc2)c2cc(F)c(F)cc2c1=O>>O=C(O)c1cn(-c2ccc(O)cc2)c2cc(F)c(F)cc2c1=O | FC=1C=C2C(C(=CN(C2=CC1F)C1=CC=C(C=C1)OC)C(=O)OCC)=O.Br>>FC=1C=C2C(C(=CN(C2=CC1F)C1=CC=C(C=C1)O)C(=O)O)=O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][n:6](-[c:7]2[cH:8][cH:9][c:10]([O:11]C)[cH:12][cH:13]2)[c:14]2[cH:15][c:16]([F:17])[c:18]([F:19])[cH:20][c:21]2[c:22]1=[O:23]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6](-[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]2)[c:14]2[cH:15][c:16]([F:17])[c:18]([F:19])[cH:20][c:21]2[c:22]1=[O:23] | CCOC(=O)c1cn(-c2ccc(OC)cc2)c2cc(F)c(F)cc2c1=O | O=C(O)c1cn(-c2ccc(O)cc2)c2cc(F)c(F)cc2c1=O | null | null | null | Deprotection | OtherReaction | 4cea9c1cf4071f9c3a5e0d042ee7e87c9888ee05636b0c5b9dfd162b490d7fb6 | 707aece9d1d6de1fa508344f68d9f46b61d18785c603f5e19232e661c94aa284 | O=c1ccn(-c2ccccc2)c2ccccc12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6].C-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10] | 92.2 | [{"value": 92.2, "product": "FC=1C=C2C(C(=CN(C2=CC1F)C1=CC=C(C=C1)O)C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To ethyl 6,7-difluoro-1-(4-methoxyphenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.70 g) is added 48% hydrobromic acid (8 ml), and the mixture is stirred at 100°-110° C. for 3 hour. After cooling, the precipitated crystals are separated by filtration, washed with water and recrystallized from dichloromethane-ethanol... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Carboxylic acid.Aromatic alcohol | null | null | c1ccccc1.c1ccc2ncccc2c1 | Other | null | null | 3 | CCOC(=O)c1cn(-c2ccc(OC)cc2)c2cc(F)c(F)cc2c1=O>>O=C(O)c1cn(-c2ccc(O)cc2)c2cc(F)c(F)cc2c1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a6b3182d98c34f5c86077f7c0968b460 | CCOC(=O)CC(=O)OCC.O=C(Cl)c1cc(F)c(F)c(F)c1F>>CCOC(=O)C(C(=O)OCC)C(=O)c1cc(F)c(F)c(F)c1F | [Mg].FC1=C(C(=O)Cl)C=C(C(=C1F)F)F.S(O)(O)(=O)=O.C(CC(=O)OCC)(=O)OCC>>FC1=C(C(=O)C(C(=O)OCC)C(=O)OCC)C=C(C(=C1F)F)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[O:9][CH2:10][CH3:11].Cl[C:12](=[O:13])[c:14]1[cH:15][c:16]([F:17])[c:18]([F:19])[c:20]([F:21])[c:22]1[F:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[C:12](=[O:13])[c:14]1[cH:15][c:16]([F:17])[c:18]([F:19])[c:20]([F:21])[c:22]1[F:23] | CCOC(=O)CC(=O)OCC.O=C(Cl)c1cc(F)c(F)c(F)c1F | CCOC(=O)C(C(=O)OCC)C(=O)c1cc(F)c(F)c(F)c1F | null | null | CCOCC.C(Cl)(Cl)(Cl)Cl.C(C)O | C-C Coupling | OtherReaction | 872dd4ea89053916cf9ee557745988425973a0fb6c3fde7e681bde82864a0018 | a7050091370b27e4945622bf444949c46249e49bd26e357ae44671cc72030a02 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10](-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 10 | MINUTE | Magnesium ribbon (0.11 g) is suspended in absolute ethanol (0.5 ml), and thereto is added carbon tetrachloride (0.05 ml). After 10 minutes, to the mixture is added dropwise a mixture of diethyl malonate (1.5 ml), absolute ethanol (0.9 ml) and anhydrous ether (3.8 ml) at room temperature. After the addition, the mixture... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Ester | Ketone | null | null | c1ccccc1 | HCl | CCOCC.C(Cl)(Cl)(Cl)Cl.C(C)O | null | 0.166667 | CCOC(=O)CC(=O)OCC.O=C(Cl)c1cc(F)c(F)c(F)c1F>CCOCC.C(Cl)(Cl)(Cl)Cl.C(C)O>CCOC(=O)C(C(=O)OCC)C(=O)c1cc(F)c(F)c(F)c1F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e9953d96b0b040d9bc639c8aaf22b596 | CCOC(=O)CC(=O)c1cc(F)c(F)c(F)c1F.CCOC([O-])[O-]>>CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(F)c(F)c1F | FC1=C(C(=O)CC(=O)OCC)C=C(C(=C1F)F)F.C(OCC)([O-])[O-].C(C)(=O)OC(C)=O>>FC1=C(C(=O)C(C(=O)OCC)=COCC)C=C(C(=C1F)F)F | [CH2:5]([C:6](=[O:7])[O:8][CH2:9][CH3:10])[C:11](=[O:12])[c:13]1[cH:14][c:15]([F:16])[c:17]([F:18])[c:19]([F:20])[c:21]1[F:22].[O-][CH:4]([O-])[O:3][CH2:2][CH3:1]>>[CH3:1][CH2:2][O:3][CH:4]=[C:5]([C:6](=[O:7])[O:8][CH2:9][CH3:10])[C:11](=[O:12])[c:13]1[cH:14][c:15]([F:16])[c:17]([F:18])[c:19]([F:20])[c:21]1[F:22] | CCOC(=O)CC(=O)c1cc(F)c(F)c(F)c1F.CCOC([O-])[O-] | CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(F)c(F)c1F | null | null | null | C-C Coupling | OtherReaction | 639a4ce9226015e35f6437fdf707a9468b6252f0523264bdae9fa6f28cb22374 | c4e4f7b42a406bead919c0be81d4397946ea7bc6e68a2cd47e017aa044114e5b | c1ccccc1 | [C:1]-[#8:2]-[CH;D3;+0:3](-[O-])-[O-].[C:4]-[#8:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11]>>[C:1]-[#8:2]-[CH;D2;+0:3]=[C;H0;D3;+0:8](-[C:9](=[O;D1;H0:10])-[c:11])-[C:6](=[O;D1;H0:7])-[#8:5]-[C:4] | 94.3 | [{"value": 94.3, "product": "FC1=C(C(=O)C(C(=O)OCC)=COCC)C=C(C(=C1F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | A mixture of ethyl α-(2,3,4,5-tetrafluorobenzoyl)acetate (0.7 g), ethyl orthoformate (0.67 g) and acetic anhydride (0.74 g) is heated at 150° C. for 1.5 hours. After the reaction, the volatile material is distilled off at 120° C. under reduced pressure with a water pump to give ethyl 2-(2,3,4,5-tetrafluorobenzoyl)-3-et... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ether | Ketone.Ester.Ether | null | null | c1ccccc1 | HO- | null | 150 | null | CCOC(=O)CC(=O)c1cc(F)c(F)c(F)c1F.CCOC([O-])[O-]>>CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(F)c(F)c1F |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a9304fd128cd465193acaec345266e54 | CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(F)c(F)c1F.COc1ccc(N)cc1>>CCOC(=O)c1cn(-c2ccc(OC)cc2)c2c(F)c(F)c(F)cc2c1=O | FC1=C(C(=O)C(C(=O)OCC)=COCC)C=C(C(=C1F)F)F.COC1=CC=C(C=C1)N>>FC=1C=C2C(C(=CN(C2=C(C1F)F)C1=CC=C(C=C1)OC)C(=O)OCC)=O | CCO[CH:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:26]([c:25]1[c:17](F)[c:18]([F:19])[c:20]([F:21])[c:22]([F:23])[cH:24]1)=[O:27].[NH2:8][c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8](-[c:9]2[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]2)[c:17]2[c:18](... | CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(F)c(F)c1F.COc1ccc(N)cc1 | CCOC(=O)c1cn(-c2ccc(OC)cc2)c2c(F)c(F)c(F)cc2c1=O | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 9dfa2a13ba72e95a01b7c2b7d6c6781347ce1f46c70cef324e6d3c157c197184 | fd972df67a445b3c88629a5a981d206d18e5e3880229f42b36ea38785357f491 | O=c1ccn(-c2ccccc2)c2ccccc12 | C-C-O-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:9](:[c:10]):[c;H0;D3;+0:11](-F):[c:12](-[F;D1;H0:13]):[c:14].[NH2;D1;+0:15]-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:19]:[c:20]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:15](-[c;H0;D3;+0:16](:... | 80.5 | [{"value": 80.5, "product": "FC=1C=C2C(C(=CN(C2=C(C1F)F)C1=CC=C(C=C1)OC)C(=O)OCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | A mixture of ethyl 2-(2,3,4,5-tetrafluorobenzoyl)-3-ethoxyacrylate (0.4 g), p-anisidine (0.15 g) and ethanol (4 ml) is stirred at room temperature for 30 minutes. After the reaction, the solvent is distilled off under reduced pressure. To the resulting residue is added anhydrous dioxane (10 ml) and further added portio... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ketone.Ester.Ether.Primary amine | Ester | c1ccccc1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1 | HF | C(C)O | null | 0.5 | CCOC=C(C(=O)OCC)C(=O)c1cc(F)c(F)c(F)c1F.COc1ccc(N)cc1>C(C)O>CCOC(=O)c1cn(-c2ccc(OC)cc2)c2c(F)c(F)c(F)cc2c1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9a8c22c9c71341ed95c00f59bcfa37b2 | CCOC(=O)c1cn(-c2ccc(OC)cc2)c2c(F)c(F)c(F)cc2c1=O>>COc1ccc(-n2cc(C(=O)O)c(=O)c3cc(F)c(F)c(F)c32)cc1 | FC=1C=C2C(C(=CN(C2=C(C1F)F)C1=CC=C(C=C1)OC)C(=O)OCC)=O.Cl>>FC=1C=C2C(C(=CN(C2=C(C1F)F)C1=CC=C(C=C1)OC)C(=O)O)=O | CC[O:12][C:10]([c:9]1[cH:8][n:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:25][cH:24]2)[c:23]2[c:15]([c:13]1=[O:14])[cH:16][c:17]([F:18])[c:19]([F:20])[c:21]2[F:22])=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13](=[O:14])[c:15]3[cH:16][c:17]([F:18])[c:19]([F:20])[c:21]([F:2... | CCOC(=O)c1cn(-c2ccc(OC)cc2)c2c(F)c(F)c(F)cc2c1=O | COc1ccc(-n2cc(C(=O)O)c(=O)c3cc(F)c(F)c(F)c32)cc1 | null | null | C(C)(=O)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccn(-c2ccccc2)c2ccccc12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 87.6 | [{"value": 87.6, "product": "FC=1C=C2C(C(=CN(C2=C(C1F)F)C1=CC=C(C=C1)OC)C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A mixture of ethyl 6,7,8-trifluoro-1-(4-methoxyphenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.37 g), conc. hydrochloric acid (1 ml) and 90% acetic acid (4 ml) is heated at 120° C. for one hour. After cooling, the precipitated crystals are separated by filtration, washed well with water and with a mixture of ethano... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2ncccc2c1 | Other | C(C)(=O)O | 120 | null | CCOC(=O)c1cn(-c2ccc(OC)cc2)c2c(F)c(F)c(F)cc2c1=O>C(C)(=O)O>COc1ccc(-n2cc(C(=O)O)c(=O)c3cc(F)c(F)c(F)c32)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-705267c2952f4b7e8eb49b392fb3da0d | CCOC(=O)c1cn(-c2ccc(OC)cc2)c2c(F)c(F)c(F)cc2c1=O>>O=C(O)c1cn(-c2ccc(O)cc2)c2c(F)c(F)c(F)cc2c1=O | FC=1C=C2C(C(=CN(C2=C(C1F)F)C1=CC=C(C=C1)OC)C(=O)OCC)=O.Br>>FC=1C=C2C(C(=CN(C2=C(C1F)F)C1=CC=C(C=C1)O)C(=O)O)=O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][n:6](-[c:7]2[cH:8][cH:9][c:10]([O:11]C)[cH:12][cH:13]2)[c:14]2[c:15]([F:16])[c:17]([F:18])[c:19]([F:20])[cH:21][c:22]2[c:23]1=[O:24]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6](-[c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][cH:13]2)[c:14]2[c:15]([F:16])[c:17]([F:18])[c:19]([F:20])[cH:21][c:22]2[c:... | CCOC(=O)c1cn(-c2ccc(OC)cc2)c2c(F)c(F)c(F)cc2c1=O | O=C(O)c1cn(-c2ccc(O)cc2)c2c(F)c(F)c(F)cc2c1=O | null | null | null | Deprotection | OtherReaction | 4cea9c1cf4071f9c3a5e0d042ee7e87c9888ee05636b0c5b9dfd162b490d7fb6 | 707aece9d1d6de1fa508344f68d9f46b61d18785c603f5e19232e661c94aa284 | O=c1ccn(-c2ccccc2)c2ccccc12 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6].C-[O;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1].[OH;D1;+0:7]-[c:8](:[c:9]):[c:10] | 79.1 | [{"value": 79.1, "product": "FC=1C=C2C(C(=CN(C2=C(C1F)F)C1=CC=C(C=C1)O)C(=O)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A mixture of ethyl 6,7,8-trifluro-1-(4-methoxyphenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate (0.37 g) and 47% hydrobromic acid (4 ml) is heated at 120° C. for 3 hours. After cooling, the precipitated crystals are separated by filtration, washed with water and further with a mixture of ethanol and ether to give 6,7,8-... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Carboxylic acid.Aromatic alcohol | null | null | c1ccccc1.c1ccc2ncccc2c1 | Other | null | 120 | null | CCOC(=O)c1cn(-c2ccc(OC)cc2)c2c(F)c(F)c(F)cc2c1=O>>O=C(O)c1cn(-c2ccc(O)cc2)c2c(F)c(F)c(F)cc2c1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-36797adabbb24c9bb133c595c901128e | O=S(Cl)Cl.OCCN1CCN([C@@H]2C[C@@H](c3ccc(F)cc3)c3ccc(F)cc32)CC1>>Cl.Cl.Fc1ccc([C@@H]2C[C@@H](N3CCN(CCCl)CC3)c3ccccc32)cc1 | FC1=CC=C(C=C1)[C@@H]1C[C@H](C2=CC(=CC=C12)F)N1CCN(CC1)CCO.S(=O)(Cl)Cl.CN(C)C=O>>Cl.Cl.FC1=CC=C(C=C1)[C@@H]1C[C@H](C2=CC=CC=C12)N1CCN(CC1)CCCl | O=S([Cl:1])[Cl:17].O[CH2:16][CH2:15][N:14]1[CH2:13][CH2:12][N:11]([C@@H:10]2[CH2:9][C@@H:8]([c:7]3[cH:6][cH:5][c:4]([F:3])[cH:27][cH:26]3)[c:25]3[c:20]2[cH:21][c:22](F)[cH:23][cH:24]3)[CH2:19][CH2:18]1>>[ClH:1].[ClH:2].[F:3][c:4]1[cH:5][cH:6][c:7]([C@@H:8]2[CH2:9][C@@H:10]([N:11]3[CH2:12][CH2:13][N:14]([CH2:15][CH2:16]... | O=S(Cl)Cl.OCCN1CCN([C@@H]2C[C@@H](c3ccc(F)cc3)c3ccc(F)cc32)CC1 | Cl.Cl.Fc1ccc([C@@H]2C[C@@H](N3CCN(CCCl)CC3)c3ccccc32)cc1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | f6599157724ea6c8033299a118d7ea5e226f20f70305d9e70b4b085220711b97 | d71ecc5f3029d2fdb0e2cf3bb3a6a26903352efa31204a3ca291eccc792fcf8f | c1ccc([C@@H]2C[C@@H](N3CCNCC3)c3ccccc32)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O-[CH2;D2;+0:6]-[C:7]-[#7:8].O=S(-[Cl;H0;D1;+0:9])-[Cl;H0;D1;+0:10]>>[#7:8]-[C:7]-[CH2;D2;+0:6]-[Cl;H0;D1;+0:9].[c:3]:[c:2]:[cH;D2;+0:1]:[c:4]:[c:5].[ClH;D0;+0:10] | null | [] | null | null | null | null | A mixture of trans-4-[3-(4-fluorophenyl)-6-fluoro-indan-1-yl]-1-piperazineethanol (40 g, 0.11 mol), thionylchloride (15 ml) and DMF (0.7 ml) in methylene chloride (400 ml) was refluxed for 1 hour. After cooling, the crystalline solid was filtered and washed on the filter with ethyl acetate and ether to give trans 1-[3-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Primary halide | c1ccc2c(c1)CCC2 | c1ccc2c(c1)CCC2 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2c(c1)CCC2 | Other | C(Cl)Cl | null | null | O=S(Cl)Cl.OCCN1CCN([C@@H]2C[C@@H](c3ccc(F)cc3)c3ccc(F)cc32)CC1>C(Cl)Cl>Cl.Cl.Fc1ccc([C@@H]2C[C@@H](N3CCN(CCCl)CC3)c3ccccc32)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-46f62c02083c4c5dbc7307d1cee9091d | C1CNCCN1.O=C1NCCN1CCCl>>O=C1NCCN1CCN1CCNCC1 | N1CCNCC1.ClCCN1C(NCC1)=O.C([O-])([O-])=O.[Na+].[Na+].ClCCN1C(NCC1)=O>>N1(C(NCC1)=O)CCN1CCNCC1 | [NH:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1.Cl[CH2:8][CH2:7][N:6]1[C:2](=[O:1])[NH:3][CH2:4][CH2:5]1>>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][N:6]1[CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1 | C1CNCCN1.O=C1NCCN1CCCl | O=C1NCCN1CCN1CCNCC1 | null | null | CO.C(C)O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 61ec49e5207aa33ebff7094bb66b1d997d4af14524931a8b3643ef7a94219a9a | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1NCCN1CCN1CCNCC1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:5]=[C:4]-[#7:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1 | 60.5 | [{"value": 60.5, "product": "N1(C(NCC1)=O)CCN1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | A mixture of piperazine (86 g, 1.0 mol), 1-(2-chloroethyl)-imidazolidin-2-one (74 g, 0.5 mol) and sodium carbonate (159 g, 1.5 mol) in ethanol (500 ml) was refluxed with stirring for 1.5 hours. A solution of 1-(2-chloroethyl)-imidazolidin-2-one (74 g, 0.5 mol) in methanol (75 ml) was then added in the course of 1.5 hou... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCCN1 | C1C[NH]CCN1 | C1C[NH]CN1.C1C[NH]CCN1 | HCl | CO.C(C)O | null | 1.5 | C1CNCCN1.O=C1NCCN1CCCl>CO.C(C)O>O=C1NCCN1CCN1CCNCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-117875f1ff4345cb90ccb856fbe3a579 | O=C(CCCl)c1ccc2c(c1)OCO2.c1ccc(N2CCNCC2)cc1>>O=C(CCN1CCN(c2ccccc2)CC1)c1ccc2c(c1)OCO2 | O.ClCCC(=O)C1=CC2=C(OCO2)C=C1.C1(=CC=CC=C1)N1CCNCC1.C(C)N(CC)CC>>C1(=CC=CC=C1)N1CCN(CC1)CCC(=O)C1=CC2=C(OCO2)C=C1 | Cl[CH2:4][CH2:3][C:2](=[O:1])[c:17]1[cH:18][cH:19][c:20]2[c:21]([cH:22]1)[O:23][CH2:24][O:25]2.[NH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][CH2:16]1>>[O:1]=[C:2]([CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][CH2:16]1)[c:17]1[cH:18][cH:19][c... | O=C(CCCl)c1ccc2c(c1)OCO2.c1ccc(N2CCNCC2)cc1 | O=C(CCN1CCN(c2ccccc2)CC1)c1ccc2c(c1)OCO2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCN1CCN(c2ccccc2)CC1)c1ccc2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[O;D1;H0:4]=[C:3](-[c:5])-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1 | 84 | [{"value": 84.0, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCC(=O)C1=CC2=C(OCO2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.8, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCC(=O)C1=CC2=C(OCO2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | 5-(3-Chloropropionyl)-1,3-benzodioxole (3 g) and N-phenylpiperazine (2.4 g) were dissolved in DMF (20 ml), triethylamine (1.7 g) was then added and the mixture was stirred for 10 hours at room temperature. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)OCO2 | HCl | CN(C)C=O | null | 10 | O=C(CCCl)c1ccc2c(c1)OCO2.c1ccc(N2CCNCC2)cc1>CN(C)C=O>O=C(CCN1CCN(c2ccccc2)CC1)c1ccc2c(c1)OCO2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-17226ab2322e46c6971ba7c794622dcd | O=C(CCCCl)c1ccc2c(c1)OCO2>>Cl.Cl.c1ccc2c(c1)OCO2 | O.ClCCCC(=O)C1=CC2=C(OCO2)C=C1.C1(=CC=CC=C1)N1CCNCC1.C(C)N(CC)CC>>Cl.Cl.O1COC2=C1C=CC=C2 | O=C(CCC[Cl:1])[c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[O:9][CH2:10][O:11]2>>[ClH:1].[ClH:2].[cH:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[O:9][CH2:10][O:11]2 | O=C(CCCCl)c1ccc2c(c1)OCO2 | Cl.Cl.c1ccc2c(c1)OCO2 | null | null | CN(C)C=O | Miscellaneous | OtherReaction | eb7d3e7edb770099a09c961b38b1287df706e91a8fee44f68434ac9cf2aae84c | 7aa8d168cdd08e5d28a7289598b8ce54a9572c79903d5368c2019b1e4077ead0 | c1ccc2c(c1)OCO2 | O=C(-C-C-C-[Cl;H0;D1;+0:1])-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]-[#8:7]>>[#8:7]-[c:6]:[c:5]:[cH;D2;+0:2]:[c:3]:[c:4].[ClH;D0;+0:1] | 296.3 | [{"value": 68.0, "product": "Cl.Cl.O1COC2=C1C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 296.3, "product": "Cl.Cl.O1COC2=C1C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To 5-(4-chlorobutyryl)-1,3-benzodioxole (4.0 g) and N-phenylpiperazine (3.0 g) dissolved in DMF (25 ml) was added triethylamine (2.2 g) and the mixture was heated at 80° C. for 40 hours under stirring. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The ext... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | null | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | c1ccc2c(c1)OCO2 | HO- | CN(C)C=O | 80 | null | O=C(CCCCl)c1ccc2c(c1)OCO2>CN(C)C=O>Cl.Cl.c1ccc2c(c1)OCO2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7f5d715623e841f083ce610c50112df4 | O=C(CCCN1CCN(c2ccccc2)CC1)c1ccc2c(c1)OCO2.[Cl-].[Cl-]>>Cl.Cl.OC(CCCN1CCN(c2ccccc2)CC1)c1ccc2c(c1)OCO2 | [Cl-].[Cl-].C1(=CC=CC=C1)N1CCN(CC1)CCCC(=O)C1=CC2=C(OCO2)C=C1.[OH-].[Na+].[BH4-].[Na+]>>Cl.Cl.C1(=CC=CC=C1)N1CCN(CC1)CCCC(O)C1=CC2=C(OCO2)C=C1 | [O:3]=[C:4]([CH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1)[c:20]1[cH:21][cH:22][c:23]2[c:24]([cH:25]1)[O:26][CH2:27][O:28]2.[Cl-:1].[Cl-:2]>>[ClH:1].[ClH:2].[OH:3][CH:4]([CH2:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][N:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][... | O=C(CCCN1CCN(c2ccccc2)CC1)c1ccc2c(c1)OCO2.[Cl-].[Cl-] | Cl.Cl.OC(CCCN1CCN(c2ccccc2)CC1)c1ccc2c(c1)OCO2 | null | null | CO | Miscellaneous | OtherReaction | 3acb0f0b694cda073872dce576343e89e8e5c30f95d996ba4b078672e8ea17cd | 65c0f1e474134afe581396038c9eec1081d3cf2c66a067b33a419661521d5253 | c1ccc(N2CCN(CCCCc3ccc4c(c3)OCO4)CC2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7].[Cl-;H0;D0:8].[Cl-;H0;D0:9]>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7].[ClH;D0;+0:8].[ClH;D0;+0:9] | 182.5 | [{"value": 62.0, "product": "Cl.Cl.C1(=CC=CC=C1)N1CCN(CC1)CCCC(O)C1=CC2=C(OCO2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 182.5, "product": "Cl.Cl.C1(=CC=CC=C1)N1CCN(CC1)CCCC(O)C1=CC2=C(OCO2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | 5-[4-(4-Phenyl-1-piperazinyl)butyryl]-1,3-benzodioxole dichloride (3.8 g) as prepared in Example 2 was suspended in methanol (50 ml) and 2N sodium hydroxide solution (4.5 ml) and then sodium borohydride (0.5 g) were added. The mixture was stirred for 10 hours at room temperature and the solvent was then distilled off. ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Secondary alcohol | null | null | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)OCO2 | null | CO | null | 10 | O=C(CCCN1CCN(c2ccccc2)CC1)c1ccc2c(c1)OCO2.[Cl-].[Cl-]>CO>Cl.Cl.OC(CCCN1CCN(c2ccccc2)CC1)c1ccc2c(c1)OCO2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-75fa5284301e4ade82a6428f4e925b67 | O=C(CCCl)Nc1ccc2c(c1)OCO2.c1ccc(N2CCNCC2)cc1>>O=C(CCN1CCN(c2ccccc2)CC1)Nc1ccc2c(c1)OCO2 | ClCCC(=O)NC1=CC2=C(C=C1)OCO2.C1(=CC=CC=C1)N1CCNCC1.C(C)N(CC)CC>>C1(=CC=CC=C1)N1CCN(CC1)CCC(=O)NC1=CC2=C(C=C1)OCO2 | Cl[CH2:4][CH2:3][C:2](=[O:1])[NH:17][c:18]1[cH:19][cH:20][c:21]2[c:22]([cH:23]1)[O:24][CH2:25][O:26]2.[NH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][CH2:16]1>>[O:1]=[C:2]([CH2:3][CH2:4][N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][CH2:16]1)[NH:17][c:18]1[c... | O=C(CCCl)Nc1ccc2c(c1)OCO2.c1ccc(N2CCNCC2)cc1 | O=C(CCN1CCN(c2ccccc2)CC1)Nc1ccc2c(c1)OCO2 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C(CCN1CCN(c2ccccc2)CC1)Nc1ccc2c(c1)OCO2 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3](=[O;D1;H0:4])-[#7:5]-[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:4]=[C:3](-[#7:5]-[c:6])-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1 | 109.5 | [{"value": 90.0, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCC(=O)NC1=CC2=C(C=C1)OCO2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 109.5, "product": "C1(=CC=CC=C1)N1CCN(CC1)CCC(=O)NC1=CC2=C(C=C1)OCO2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 20 | HOUR | To N-(3-chloropropionyl)-3,4-methylenedioxyaniline (2.0 g) dissolved in N,N-dimethylformamide (20 ml) were added N-phenylpiperazine (1.6 g) and triethylamine (3 ml) and the mixture was stirred at 80° C. for 20 hours in a nitrogen atmosphere. The reaction mixture was evaporated in vacuo and to the residue were added eth... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2c(c1)OCO2 | HCl | CN(C=O)C | 80 | 20 | O=C(CCCl)Nc1ccc2c(c1)OCO2.c1ccc(N2CCNCC2)cc1>CN(C=O)C>O=C(CCN1CCN(c2ccccc2)CC1)Nc1ccc2c(c1)OCO2 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5fb9655e153e473989509987f2918670 | CCOC(OCC)OCC.C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OC3CCCCO3)CC[C@@H]12>>CCOC(OCC)[C@@H]1C[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OC4CCCCO4)CC[C@@H]32)CC1=O | C(C)(C)N(CC)C(C)C.B(F)(F)F.CCOCC.C(C)OC(OCC)OCC.O1C(CCCC1)O[C@@H]1[C@]2(C)[C@@H](CC1)[C@@H]1CC[C@H]3CC(CC[C@]3(C)[C@H]1CC2)=O>>C(C)OC([C@H]1C(C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@]2(C1)C)OC1OCCCC1)=O)OCC | CCO[CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7].[CH2:8]1[CH2:9][C@@:10]2([CH3:11])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:16]2[CH2:17][CH2:18][C@:19]2([CH3:20])[C@@H:21]([O:22][CH:23]4[CH2:24][CH2:25][CH2:26][CH2:27][O:28]4)[CH2:29][CH2:30][C@@H:31]32)[CH2:32][C:33]1=[O:34]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][C... | CCOC(OCC)OCC.C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OC3CCCCO3)CC[C@@H]12 | CCOC(OCC)[C@@H]1C[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OC4CCCCO4)CC[C@@H]32)CC1=O | null | null | ClCCl | C-C Coupling | OtherReaction | 256f1f1c0751ccd4a5b5e92807ba0f3ef141a0fd20b2d48ea9d34dbd8c9e3323 | 155bcdfe4c4a838582eb097f30902e58c733d6d3e0c4634faa32630a07995baa | O=C1CCC2[C@@H](CC[C@@H]3[C@@H]2CCC2[C@@H](OC4CCCCO4)CC[C@H]23)C1 | C-C-O-[CH;D3;+0:1](-[#8:2]-[C:3])-[#8:4]-[C:5].[C:6]-[C:7]-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[C:11]>>[C:6]-[C:7]-[C@@H;D3;+0:8](-[CH;D3;+0:1](-[#8:2]-[C:3])-[#8:4]-[C:5])-[C:9](=[O;D1;H0:10])-[C:11] | 49.3 | [{"value": 49.0, "product": "C(C)OC([C@H]1C(C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@]2(C1)C)OC1OCCCC1)=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.3, "product": "C(C)OC([C@H]1C(C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@]2(C1)C)OC1OCCCC1)=O)OCC", "details": "CALCULATEDPE... | 0 | CELSIUS | 15 | MINUTE | Under an argon atmosphere at less than -30° C. boron trifluoride etherate (100 ml., 115.4 g., 0.704 mole) was added to a solution of triethylorthoformate (109.5 ml., 97.56 g., 0.658 mole) in dichloromethane (300 ml.). The temperature was raised to 0° C., kept there for 15 min., then lowered to -70° C. A solution of (5α... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Ether | Ketone.Ether.Ether | C1CC[C@H]2[C@H](C1)CC[C@@H]1[C@@H]2CC[C@@H]2CCC[C@H]21 | C1CC[C@H]2[C@H](C1)CC[C@@H]1[C@@H]2CC[C@@H]2CCC[C@H]21 | C1CCOCC1.C1CC[C@H]2[C@H](C1)CC[C@@H]1[C@@H]2CC[C@@H]2CCC[C@H]21 | HO- | ClCCl | 0 | 0.25 | CCOC(OCC)OCC.C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OC3CCCCO3)CC[C@@H]12>ClCCl>CCOC(OCC)[C@@H]1C[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OC4CCCCO4)CC[C@@H]32)CC1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e63f7957dff241c5a1dd872f8df4f4b8 | CCOC(OCC)OCC.C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12>>CCOC(OCC)[C@@H]1C[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]32)CC1=O | FC(C(=O)O)(F)F.O[C@@H]1[C@]2(C)[C@@H](CC1)[C@@H]1CC[C@H]3CC(CC[C@]3(C)[C@H]1CC2)=O.C(C)OC(OCC)OCC>>FC(C(=O)O)(F)F.C(C)OC([C@H]1C(C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@]2(C1)C)O)=O)OCC | CCO[CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7].[CH2:8]1[CH2:9][C@@:10]2([CH3:11])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:16]2[CH2:17][CH2:18][C@:19]2([CH3:20])[C@@H:21]([OH:22])[CH2:23][CH2:24][C@@H:25]32)[CH2:26][C:27]1=[O:28]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[C@@H:8]1[CH2:9][C@@:10]2([CH3:11])[C@@H... | CCOC(OCC)OCC.C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12 | CCOC(OCC)[C@@H]1C[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]32)CC1=O | null | null | B(F)(F)F.CCOCC | C-C Coupling | OtherReaction | 256f1f1c0751ccd4a5b5e92807ba0f3ef141a0fd20b2d48ea9d34dbd8c9e3323 | 155bcdfe4c4a838582eb097f30902e58c733d6d3e0c4634faa32630a07995baa | O=C1CCC2[C@@H](CC[C@H]3[C@@H]4CCCC4CC[C@H]23)C1 | C-C-O-[CH;D3;+0:1](-[#8:2]-[C:3])-[#8:4]-[C:5].[C:6]-[C:7]-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[C:11]>>[C:6]-[C:7]-[C@@H;D3;+0:8](-[CH;D3;+0:1](-[#8:2]-[C:3])-[#8:4]-[C:5])-[C:9](=[O;D1;H0:10])-[C:11] | 71 | [{"value": 71.0, "product": "FC(C(=O)O)(F)F.C(C)OC([C@H]1C(C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@]2(C1)C)O)=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method of part A of Example 20 (5α,17β)-17-hydroxyandrostan-3-one trifluoroacetate (ester) (0.344 mole) was diethoxymethylated using triethylorthoformate (126 ml.) and boron trifluoride etherate (140 ml.). The product was crystallized from methanol, affording (2α,5α,17β)-2-(diethoxymethyl)-17-hydroxyandrostan-3-... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Ether | Ketone.Ether.Ether | C1CC[C@H]2[C@H](C1)CC[C@@H]1[C@@H]2CC[C@@H]2CCC[C@H]21 | C1CC[C@H]2[C@H](C1)CC[C@@H]1[C@@H]2CC[C@@H]2CCC[C@H]21 | C1CC[C@H]2[C@H](C1)CC[C@@H]1[C@@H]2CC[C@@H]2CCC[C@H]21 | HO- | B(F)(F)F.CCOCC | null | null | CCOC(OCC)OCC.C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12>B(F)(F)F.CCOCC>CCOC(OCC)[C@@H]1C[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]32)CC1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2b1b0fd95f8c46db929f42c1c3e98c4e | CCOC(OCC)OCC.CO[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C>>CCOC(OCC)[C@@H]1C[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OC)CC[C@@H]32)CC1=O | CO[C@@H]1[C@]2(C)[C@@H](CC1)[C@@H]1CC[C@H]3CC(CC[C@]3(C)[C@H]1CC2)=O.C(C)OC(OCC)OCC.B(F)(F)F.CCOCC>>C(C)OC([C@H]1C(C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@]2(C1)C)OC)=O)OCC | CCO[CH:4]([O:3][CH2:2][CH3:1])[O:5][CH2:6][CH3:7].[CH2:8]1[CH2:9][C@@:10]2([CH3:11])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:16]2[CH2:17][CH2:18][C@:19]2([CH3:20])[C@@H:21]([O:22][CH3:23])[CH2:24][CH2:25][C@@H:26]32)[CH2:27][C:28]1=[O:29]>>[CH3:1][CH2:2][O:3][CH:4]([O:5][CH2:6][CH3:7])[C@@H:8]1[CH2:9][C@@:10]2([CH3:11... | CCOC(OCC)OCC.CO[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C | CCOC(OCC)[C@@H]1C[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OC)CC[C@@H]32)CC1=O | null | null | null | C-C Coupling | OtherReaction | 256f1f1c0751ccd4a5b5e92807ba0f3ef141a0fd20b2d48ea9d34dbd8c9e3323 | 155bcdfe4c4a838582eb097f30902e58c733d6d3e0c4634faa32630a07995baa | O=C1CCC2[C@@H](CC[C@H]3[C@@H]4CCCC4CC[C@H]23)C1 | C-C-O-[CH;D3;+0:1](-[#8:2]-[C:3])-[#8:4]-[C:5].[C:6]-[C:7]-[CH2;D2;+0:8]-[C:9](=[O;D1;H0:10])-[C:11]>>[C:6]-[C:7]-[C@@H;D3;+0:8](-[CH;D3;+0:1](-[#8:2]-[C:3])-[#8:4]-[C:5])-[C:9](=[O;D1;H0:10])-[C:11] | 117.7 | [{"value": 117.7, "product": "C(C)OC([C@H]1C(C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@@]4(C)CC[C@@H]3[C@]2(C1)C)OC)=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | By the method of part A of Example 20 (5α,17β)-17-methoxyandrostan-3-one (45.67 g., 0.15 mole) was diethoxymethylated using triethylorthoformate (55.0 ml., 49.0 g., 0.33 mole) and boron trifluoride etherate (50.0 ml., 57.7 g., 0.407 mole), affording (2α,5α,17β)-2-(diethoxymethyl)-17-methoxyandrostan-3-one (71.81 g.).
C... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether.Ether | Ketone.Ether.Ether | C1CC[C@H]2[C@H](C1)CC[C@@H]1[C@@H]2CC[C@@H]2CCC[C@H]21 | C1CC[C@H]2[C@H](C1)CC[C@@H]1[C@@H]2CC[C@@H]2CCC[C@H]21 | C1CC[C@H]2[C@H](C1)CC[C@@H]1[C@@H]2CC[C@@H]2CCC[C@H]21 | HO- | null | null | null | CCOC(OCC)OCC.CO[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C>>CCOC(OCC)[C@@H]1C[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OC)CC[C@@H]32)CC1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-87387689be1e4fb4aa903dde6aeb2236 | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.NO>>CC(C)(C)[Si](ON)(c1ccccc1)c1ccccc1 | Cl.NO.C(C)N(CC)CC.[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)Cl>>[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)ON | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1.[OH:6][NH2:7]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([O:6][NH2:7])([c:8]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1 | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.NO | CC(C)(C)[Si](ON)(c1ccccc1)c1ccccc1 | null | null | CN(C)C=O | Protection | Alcohol protection with silyl ethers | 8fcc4c3cc9b76ad7a25dadc60c2bf40d0808fa925288f755ee2252a082747b94 | f0dce65f75d702dc7e016c0abdb24b26134ae5c509e2d0da4a21967fb59ed09d | c1ccc([SiH2]c2ccccc2)cc1 | Cl-[Si;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[N;D1;H2:12]-[OH;D1;+0:13]>>[C;D1;H3:9]-[C:8](-[C;D1;H3:10])(-[C;D1;H3:11])-[Si;H0;D4;+0:1](-[O;H0;D2;+0:13]-[N;D1;H2:12])(-[c:2](:[c:3]):[c:4])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 1 | HOUR | Hydroxylamine hydrochloride (3.48 g) and triethylamine (7 ml) were stirred for 0.25 hours in DMF (50 ml) at 0° C. tert-Butyldiphenylsilyl chloride (13 ml) was added and the mixture was stirred for 1 hour. The mixture was partitioned between pentane (500 ml) and water (100 ml), the layers separated and the aqueous phase... | 10.6084/m9.figshare.5104873.v1 | null | Silyl protective group | Silyl protective group | null | null | c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | null | 1 | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.NO>CN(C)C=O>CC(C)(C)[Si](ON)(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-cdb7f170466e44ea945ffad42c2724c9 | CS(=O)(=O)N1CCN(C(=O)Cl)C1=O.C[C@H](O)[C@@H](N)C(=O)O>>C[C@H](O)[C@@H](NC(=O)N1CCN(S(C)(=O)=O)C1=O)C(=O)O | N[C@H]([C@@H](O)C)C(=O)O.[OH-].[Na+].CS(=O)(=O)N1C(N(CC1)C(=O)Cl)=O.[OH-].[Na+].Cl>>O[C@H]([C@H](C(=O)O)NC(=O)N1C(N(CC1)S(=O)(=O)C)=O)C | Cl[C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([S:12]([CH3:13])(=[O:14])=[O:15])[C:16]1=[O:17].[CH3:1][C@H:2]([OH:3])[C@@H:4]([NH2:5])[C:18](=[O:19])[OH:20]>>[CH3:1][C@H:2]([OH:3])[C@@H:4]([NH:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([S:12]([CH3:13])(=[O:14])=[O:15])[C:16]1=[O:17])[C:18](=[O:19])[OH:20] | CS(=O)(=O)N1CCN(C(=O)Cl)C1=O.C[C@H](O)[C@@H](N)C(=O)O | C[C@H](O)[C@@H](NC(=O)N1CCN(S(C)(=O)=O)C1=O)C(=O)O | null | null | O.CC(=O)C | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | b66f0127f31d05607e2c1652b6b4f18487a952a502aa7b80cc303d6d5e78ce9e | fae94ce6ae5856f710438d2b0c3a2fe4ce15d644f728354de0d8947852529b84 | O=C1NCCN1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#7:3]1-[C:4]-[C:5]-[#7:6](-[#16:7])-[C:8]-1=[O;D1;H0:9].[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13](=[O;D1;H0:14])-[O;D1;H1:15]>>[#16:7]-[#7:6]1-[C:5]-[C:4]-[#7:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:12]-[C:11](-[C:10])-[C:13](=[O;D1;H0:14])-[O;D1;H1:15])-[C:8]-1=[O;D1;H0:9] | 56.3 | [{"value": 56.3, "product": "O[C@H]([C@H](C(=O)O)NC(=O)N1C(N(CC1)S(=O)(=O)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | D-Threonine (5.0 g) was suspended in water (50 ml) and treated with 2M aqueous sodium hydroxide solution to pH 10, forming a clear solution. The pH was then re-adjusted to 7.5 with concentrated hydrochloric acid and the still clear solution cooled to 15°. 3-Methanesulphonyl-2-oxoimidazolidine-1-carbonyl chloride (9.5 g... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Substituted dicarboximide.Primary amine | Urea | null | null | C1C[NH]C[NH]1 | HCl | O.CC(=O)C | null | 1 | CS(=O)(=O)N1CCN(C(=O)Cl)C1=O.C[C@H](O)[C@@H](N)C(=O)O>O.CC(=O)C>C[C@H](O)[C@@H](NC(=O)N1CCN(S(C)(=O)=O)C1=O)C(=O)O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-2145a2297f49479d9a15bdbfa4ad4a3f | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.O=C1NCCN1CCO>>CC(C)(C)[Si](OCCN1CCNC1=O)(c1ccccc1)c1ccccc1 | C(C)(C)(C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)Cl.C(C)OCC.OCCN1C(NCC1)=O.N1C=NC=C1>>[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OCCN1C(NCC1)=O | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1)[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.[OH:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][NH:12][C:13]1=[O:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([O:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][NH:12][C:13]1=[O:14])([c:15]1[cH:16][cH:17][cH:... | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.O=C1NCCN1CCO | CC(C)(C)[Si](OCCN1CCNC1=O)(c1ccccc1)c1ccccc1 | null | null | O.CN(C=O)C.C(C)(=O)OCC | Protection | Alcohol protection with silyl ethers | 16b089e75ae0faeb6299d6901714a961ddf80ba40eb5191df04d4efe8b4a1af5 | a12fb6ee4294c877f426f603ce64d893e39b302f1553f4ca246c599e7a8e7068 | O=C1NCCN1CCO[SiH](c1ccccc1)c1ccccc1 | Cl-[Si;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11].[C:12]-[C:13]-[OH;D1;+0:14]>>[C:12]-[C:13]-[O;H0;D2;+0:14]-[Si;H0;D4;+0:1](-[c:2](:[c:3]):[c:4])(-[c:5](:[c:6]):[c:7])-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11] | null | [] | null | null | 3 | HOUR | A solution of 1-(2-hydroxyethyl)-2-oxoimidazolidine (13 g) in dimethylformamide (50 ml) containing imidazole (7.5 g) was treated with t-butylchlorodiphenylsilane (28.6 ml) and the clear solution stirred for 3 hours at ambient temperature. The white suspension formed was dissolved in water (200 ml) and ethyl acetate (50... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | Silyl protective group | null | null | C1CNC[NH]1.c1ccccc1.c1ccccc1 | HCl | O.CN(C=O)C.C(C)(=O)OCC | null | 3 | CC(C)(C)[Si](Cl)(c1ccccc1)c1ccccc1.O=C1NCCN1CCO>O.CN(C=O)C.C(C)(=O)OCC>CC(C)(C)[Si](OCCN1CCNC1=O)(c1ccccc1)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a568672fc36549c5b8f0519277c91232 | NCCCCn1ccnc1.O=c1[nH]c2ccccc2c(=O)o1>>Nc1ccccc1C(=O)NCCCCn1ccnc1 | C1=2C(=O)OC(NC1=CC=CC2)=O.N1(C=NC=C1)CCCCN>>NC1=C(C(=O)NCCCCN2C=NC=C2)C=CC=C1 | [NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][n:15]1[cH:16][cH:17][n:18][cH:19]1.O=c1o[c:8](=[O:9])[c:7]2[c:2]([nH:1]1)[cH:3][cH:4][cH:5][cH:6]2>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][n:15]1[cH:16][cH:17][n:18][cH:19]1 | NCCCCn1ccnc1.O=c1[nH]c2ccccc2c(=O)o1 | Nc1ccccc1C(=O)NCCCCn1ccnc1 | null | null | C(C)O | Acylation | OtherReaction | 05f2f4b560cbf584ccb0bd125cb5ac7db8ee3251741e8cf30be7edbfdf8b694e | b609a70ccab739990a9ccc4ea2adcc77011bcd0c07154489a12420f7c0e7382e | O=C(NCCCCn1ccnc1)c1ccccc1 | O=c1:[nH;D2;+0:1]:[c:2](:[c:3]):[c:4](:[c:5]):[c;H0;D3;+0:6](=[O;D1;H0:7]):o:1.[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:4](:[c:5]):[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | null | null | 22 | HOUR | A mixture of 1.63 g of isatoic anhydride, 1.39 g of 1H-imidazole-1-butanamine and 25 ml of ethanol was stirred at room temperature for 22 hours. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate and cooled. The desired product was isolated by filtration, mp 91°-93° C.
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide.Primary amine | c1ocnc2ccccc12 | c1ccccc1 | c1ccccc1.c1c[nH]cn1 | Other | C(C)O | null | 22 | NCCCCn1ccnc1.O=c1[nH]c2ccccc2c(=O)o1>C(C)O>Nc1ccccc1C(=O)NCCCCn1ccnc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-fc25cc5cc9dc4f369eadfd7bf10dd010 | NCCCc1ncc[nH]1.O=c1[nH]c2ccccc2c(=O)o1>>Nc1ccccc1C(=O)NCCCn1ccnc1 | C1=2C(=O)OC(NC1=CC=CC2)=O.N1C(=NC=C1)CCCN>>NC1=C(C(=O)NCCCN2C=NC=C2)C=CC=C1 | [NH2:10][CH2:11][CH2:12][CH2:13][c:18]1[nH:14][cH:15][cH:16][n:17]1.O=c1o[c:8](=[O:9])[c:7]2[c:2]([nH:1]1)[cH:3][cH:4][cH:5][cH:6]2>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][n:14]1[cH:15][cH:16][n:17][cH:18]1 | NCCCc1ncc[nH]1.O=c1[nH]c2ccccc2c(=O)o1 | Nc1ccccc1C(=O)NCCCn1ccnc1 | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 081416d69508a46fbf83efc6af53a8ec726e447d39a90bcf18cbf5be16303800 | b609a70ccab739990a9ccc4ea2adcc77011bcd0c07154489a12420f7c0e7382e | O=C(NCCCn1ccnc1)c1ccccc1 | O=c1:[nH;D2;+0:1]:[c:2](:[c:3]):[c:4](:[c:5]):[c;H0;D3;+0:6](=[O;D1;H0:7]):o:1.[NH2;D1;+0:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-[c;H0;D3;+0:12]1:[#7;a:13]:[c:14]:[c:15]:[nH;D2;+0:16]:1>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4](-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[C:9]-[C:10]-[CH2;D2;+0:11]-[n;H0;D3;+0:16]1:[c:15]:[c:14]:[#7;a... | null | [] | 90 | CELSIUS | null | null | A mixture of 2.93 g of isatoic anhydride, 2.50 g of 1H-imidazole-propanamine and 30 ml of toluene was heated at 90° C. for 45 minutes and cooled. The toluene layer was decanted and the residue was dissolved in methylene chloride, washed with dilute sodium hydroxide solution, water and dried over magnesium sulfate. The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide.Primary amine | c1c[nH]cn1.c1ocnc2ccccc12 | c1ccccc1.c1c[nH]cn1 | c1ccccc1.c1c[nH]cn1 | Other | C1(=CC=CC=C1)C | 90 | null | NCCCc1ncc[nH]1.O=c1[nH]c2ccccc2c(=O)o1>C1(=CC=CC=C1)C>Nc1ccccc1C(=O)NCCCn1ccnc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-40833ac0fa4e4b34abda5babec381081 | BrCCCCCCCCCCBr.O=C1NC(=O)c2ccccc21>>O=C1c2ccccc2C(=O)N1CCCCCCCCCCBr | C.BrCCCCCCCCCCBr.C1(NC(C2=CC=CC=C12)=O)=O.[K]>>BrCCCCCCCCCCN1C(C2=CC=CC=C2C1=O)=O | Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][Br:22].[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[NH:11]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][Br:22] | BrCCCCCCCCCCBr.O=C1NC(=O)c2ccccc21 | O=C1c2ccccc2C(=O)N1CCCCCCCCCCBr | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 2022cc53c1563230994721760c16c873bbdd2982bbfbeeef5b40885f32de1173 | ed5b40ca5c14bda1cdc43d7e7526ae39e9e787b52b58ca2afd56239c19d62539 | O=C1NC(=O)c2ccccc21 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;D1;H0:4]=[C:5]1-[NH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10]-1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]1-[C:7](=[O;D1;H0:8])-[c:9]:[c:10]-[C:5]-1=[O;D1;H0:4] | 66.4 | [{"value": 66.4, "product": "BrCCCCCCCCCCN1C(C2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 100.0 g of 1,10-dibromodecane and 50.0 g of 1H-isoindole-1,3(2H)-dione, potassium salt in 500 ml of N,N-dimethylformamide was stirred and heated on a steam bath for eight hours. The reaction mixture was clarified while hot with activated charcoal, then filtered. The material on the filter was washed with 1... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Unsubstituted dicarboximide | Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HBr | CN(C=O)C | null | null | BrCCCCCCCCCCBr.O=C1NC(=O)c2ccccc21>CN(C=O)C>O=C1c2ccccc2C(=O)N1CCCCCCCCCCBr |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c1284db6c5b14f14ad6b87eb7b078f36 | O=C1c2ccccc2C(=O)N1CCCCCCCCCCBr.c1c[nH]cn1>>O=C1c2ccccc2C(=O)N1CCCCCCCCCCn1ccnc1 | N1C=NC=C1.[Na].BrCCCCCCCCCCN1C(C2=CC=CC=C2C1=O)=O.N1C=NC=C1.[H-].[Na+]>>N1(C=NC=C1)CCCCCCCCCCN1C(C2=CC=CC=C2C1=O)=O | Br[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:11]1[C:2](=[O:1])[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9]1=[O:10].[nH:22]1[cH:23][cH:24][n:25][cH:26]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:... | O=C1c2ccccc2C(=O)N1CCCCCCCCCCBr.c1c[nH]cn1 | O=C1c2ccccc2C(=O)N1CCCCCCCCCCn1ccnc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C1c2ccccc2C(=O)N1CCCCCCCCCCn1ccnc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]1:[c:5]:[c:6]:[nH;D2;+0:7]:[c:8]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[#7;a:4]:[c:8]:1 | null | [] | null | null | null | null | A 99.0 g amount of 2-(10-bromodecyl)-1H-isoindole-1,3(2H)-dione (prepared as described above) was dissolved in 300 ml of warm N,N-dimethylformamide with stirring. This solution was added to a stirred solution of 1H-imidazole, sodium salt (prepared by stirring a mixture of 20 g of imidazole and 14.0 g 50% sodium hydride... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1ccc2c(c1)C[NH]C2.c1c[nH]cn1 | HBr | CN(C=O)C | null | null | O=C1c2ccccc2C(=O)N1CCCCCCCCCCBr.c1c[nH]cn1>CN(C=O)C>O=C1c2ccccc2C(=O)N1CCCCCCCCCCn1ccnc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e6e5308386f14afbbdcf8015ffa02749 | CCOC(=O)Cl.Nc1ccccc1C(=O)NCCCn1ccnc1>>O=c1[nH]c2ccccc2c(=O)n1CCCn1ccnc1 | NC1=C(C(=O)NCCCN2C=NC=C2)C=CC=C1.ClC(=O)OCC>>N1(C=NC=C1)CCCN1C(NC2=CC=CC=C2C1=O)=O | CCO[C:2](Cl)=[O:1].[NH2:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[C:10](=[O:11])[NH:12][CH2:13][CH2:14][CH2:15][n:16]1[cH:17][cH:18][n:19][cH:20]1>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10](=[O:11])[n:12]1[CH2:13][CH2:14][CH2:15][n:16]1[cH:17][cH:18][n:19][cH:20]1 | CCOC(=O)Cl.Nc1ccccc1C(=O)NCCCn1ccnc1 | O=c1[nH]c2ccccc2c(=O)n1CCCn1ccnc1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 1eaea0eff513f98315e64e3636d3f293f826625a3d5d5e96b1fdfdf290747f39 | 948450339726da1e454fa2aca21290c9c971c60c1d1aefec6f162da5ad80abf5 | O=c1[nH]c2ccccc2c(=O)n1CCCn1ccnc1 | C-C-O-[C;H0;D3;+0:1](-Cl)=[O;D1;H0:2].[C:3]-[C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10](-[NH2;D1;+0:11]):[c:12]>>[C:3]-[C:4]-[n;H0;D3;+0:5]1:[c;H0;D3;+0:6](=[O;D1;H0:7]):[c:8](:[c:9]):[c:10](:[c:12]):[nH;D2;+0:11]:[c;H0;D3;+0:1]:1=[O;D1;H0:2] | null | [] | null | null | null | null | A mixture of 4.0 g of 2-amino-N-[3-(1H-imidazol-1-yl)propyl]benzamide and 15 ml of ethyl chloroformate was heated in an oil bath at 95°-105° C. for 1.5 hours, dissolved in 50 ml of ethanol, and concentrated. The residue was mixed with 100 ml of ethanol and 3.2 g of potassium hydroxide, heated at reflux temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary amide.Primary amine | null | c1ccccc1 | c1ncc2ccccc2n1 | c1ncc2ccccc2n1.c1c[nH]cn1 | HCl | C(C)O | null | null | CCOC(=O)Cl.Nc1ccccc1C(=O)NCCCn1ccnc1>C(C)O>O=c1[nH]c2ccccc2c(=O)n1CCCn1ccnc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-72ca5329042648c3adc923f1baeaf804 | NCCCCCn1ccnc1.O=c1[nH]c2ccccc2c(=O)o1>>O=c1[nH]c2ccccc2c(=O)n1CCCCCn1ccnc1 | N1(C=NC=C1)CCCCCN.C1=2C(=O)OC(NC1=CC=CC2)=O>>N1(C=NC=C1)CCCCCN1C(NC2=CC=CC=C2C1=O)=O | [NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][n:18]1[cH:19][cH:20][n:21][cH:22]1.o1[c:2](=[O:1])[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10]1=[O:11]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[c:10](=[O:11])[n:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][n:18]1[cH:19][cH:20][n:21][cH:22]1 | NCCCCCn1ccnc1.O=c1[nH]c2ccccc2c(=O)o1 | O=c1[nH]c2ccccc2c(=O)n1CCCCCn1ccnc1 | null | null | C(C)O | Miscellaneous | OtherReaction | 4bf75bfa5cc58668668cdefed165b50fd0e973bc03e78d9999d3ae997078b4c1 | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=c1[nH]c2ccccc2c(=O)n1CCCCCn1ccnc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[c;H0;D3;+0:5]1:o:[c;H0;D3;+0:6](=[O;D1;H0:7]):[#7;a:8]:[c:9](:[c:10]):[c:11]:1:[c:12]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[c;H0;D3;+0:5](=[O;D1;H0:4]):[c:11](:[c:12]):[c:9](:[c:10]):[#7;a:8]:[c;H0;D3;+0:6]:1=[O;D1;H0:7] | null | [] | 95 | CELSIUS | 20 | HOUR | A mixture of 1.53 g of 1H-imidazole-1-pentanamine, 1.63 g of isatoic anhydride and 15 ml at ethanol was stirred for 20 hours and concentrated. The viscous residue was mixed with 10 ml of ethyl chloroformate and heated for 1.5 hours in an oil bath at 95° C. The mixture was dissolved in ethanol, reconcentrated, mixed wit... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1nc2ccccc2co1 | c1ncc2ccccc2n1 | c1ncc2ccccc2n1.c1c[nH]cn1 | HO- | C(C)O | 95 | 20 | NCCCCCn1ccnc1.O=c1[nH]c2ccccc2c(=O)o1>C(C)O>O=c1[nH]c2ccccc2c(=O)n1CCCCCn1ccnc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f7ea0488e0cb47e498febe28e50052fb | NCCCCn1ccnc1.O=c1[nH]c2ccc(F)cc2c(=O)o1>>O=c1[nH]c2ccc(F)cc2c(=O)n1CCCCn1ccnc1 | FC1=CC=C2C(C(=O)OC(N2)=O)=C1.N1(C=NC=C1)CCCCN>>FC=1C=C2C(N(C(NC2=CC1)=O)CCCCN1C=NC=C1)=O | [NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][n:18]1[cH:19][cH:20][n:21][cH:22]1.o1[c:2](=[O:1])[nH:3][c:4]2[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]2[c:11]1=[O:12]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][cH:6][c:7]([F:8])[cH:9][c:10]2[c:11](=[O:12])[n:13]1[CH2:14][CH2:15][CH2:16][CH2:17][n:18]1[cH:19][cH:20][n:21][cH:22]1 | NCCCCn1ccnc1.O=c1[nH]c2ccc(F)cc2c(=O)o1 | O=c1[nH]c2ccc(F)cc2c(=O)n1CCCCn1ccnc1 | null | null | null | Miscellaneous | OtherReaction | e271fb7d8bb4d3880dab906e1cea5c8c9cbc4024a191b9b01351a4e8b067eb8d | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=c1[nH]c2ccccc2c(=O)n1CCCCn1ccnc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[c;H0;D3;+0:5]1:o:[c;H0;D3;+0:6](=[O;D1;H0:7]):[#7;a:8]:[c:9](:[c:10]):[c:11]:1:[c:12]>>[C:1]-[C:2]-[n;H0;D3;+0:3]1:[c;H0;D3;+0:5](=[O;D1;H0:4]):[c:11](:[c:12]):[c:9](:[c:10]):[#7;a:8]:[c;H0;D3;+0:6]:1=[O;D1;H0:7] | null | [] | null | null | null | null | When 5-fluoroisatoic anhydride and 1H-imidazole 1-butanamine are reacted by the procedure of example 24, this compound is obtained.
Conditions: See reaction.notes.procedure_details.
Workup: this compound is obtained | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccc2ncocc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1c[nH]cn1 | HO- | null | null | null | NCCCCn1ccnc1.O=c1[nH]c2ccc(F)cc2c(=O)o1>>O=c1[nH]c2ccc(F)cc2c(=O)n1CCCCn1ccnc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-05763b91920d467bbcbc6ee6a79c82e2 | O=c1[nH]c2ccc([N+](=O)[O-])cc2c(=O)n1CCCCn1ccnc1>>Nc1ccc2[nH]c(=O)n(CCCCn3ccnc3)c(=O)c2c1 | N1(C=NC=C1)CCCCN1C(NC2=CC=C(C=C2C1=O)[N+](=O)[O-])=O.[H][H]>>NC=1C=C2C(N(C(NC2=CC1)=O)CCCCN1C=NC=C1)=O | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[nH:6][c:7](=[O:8])[n:9]([CH2:10][CH2:11][CH2:12][CH2:13][n:14]3[cH:15][cH:16][n:17][cH:18]3)[c:19](=[O:20])[c:21]2[cH:22]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[nH:6][c:7](=[O:8])[n:9]([CH2:10][CH2:11][CH2:12][CH2:13][n:14]3[cH:15][cH:16][n:17][cH:18]3)[c:19](=[O:20])[c:21]2[cH:22]1 | O=c1[nH]c2ccc([N+](=O)[O-])cc2c(=O)n1CCCCn1ccnc1 | Nc1ccc2[nH]c(=O)n(CCCCn3ccnc3)c(=O)c2c1 | null | [Pd] | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=c1[nH]c2ccccc2c(=O)n1CCCCn1ccnc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A mixture of 2.0 g of 3-[4-(1H-imidazol-1-yl)butyl]-6-nitro-2,4(1H,3H)-quinazolinedione, 1.0 g of 10% palladium-on-carbon catalyst and 200 ml of ethanol is shaken in a Parr hydrogenater under 45 pounds of hydrogen pressure until the hydrogen uptake is complete. The reaction mixture is heated to the boil and the catalys... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ncncc2c1.c1c[nH]cn1 | Other | [Pd].C(C)O | null | null | O=c1[nH]c2ccc([N+](=O)[O-])cc2c(=O)n1CCCCn1ccnc1>[Pd].C(C)O>Nc1ccc2[nH]c(=O)n(CCCCn3ccnc3)c(=O)c2c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4b7d77ef5dee44eeabed2fbed6085bf0 | CC(CN)Cn1ccnc1.Cn1c(=O)oc(=O)c2ccc(Cl)cc21>>CC(Cn1ccnc1)Cn1c(=O)c2ccc(Cl)cc2n(C)c1=O | ClC=1C=C2C(C(=O)OC(N2C)=O)=CC1.N1(C=NC=C1)CC(CN)C>>ClC1=CC=C2C(N(C(N(C2=C1)C)=O)CC(CN1C=NC=C1)C)=O | [CH3:1][CH:2]([CH2:3][n:4]1[cH:5][cH:6][n:7][cH:8]1)[CH2:9][NH2:10].o1[c:11](=[O:12])[c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][c:19]2[n:20]([CH3:21])[c:22]1=[O:23]>>[CH3:1][CH:2]([CH2:3][n:4]1[cH:5][cH:6][n:7][cH:8]1)[CH2:9][n:10]1[c:11](=[O:12])[c:13]2[cH:14][cH:15][c:16]([Cl:17])[cH:18][c:19]2[n:20]([CH3:21])[c:22]... | CC(CN)Cn1ccnc1.Cn1c(=O)oc(=O)c2ccc(Cl)cc21 | CC(Cn1ccnc1)Cn1c(=O)c2ccc(Cl)cc2n(C)c1=O | null | null | C(C)O | Miscellaneous | OtherReaction | 4ae59ff23cd5d975888112d390c3fa191e1ac24dd9f2b09e36e0112861b9202b | 74f861e099b6420f2f6d4f3094b402eaca1d0baec018283dff42a39bacc23c31 | O=c1[nH]c2ccccc2c(=O)n1CCCn1ccnc1 | [C;D1;H3:1]-[#7;a:2]1:[c:3](:[c:4]):[c:5](:[c:6]):[c;H0;D3;+0:7](=[O;D1;H0:8]):o:[c;H0;D3;+0:9]:1=[O;D1;H0:10].[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[n;H0;D3;+0:13]1:[c;H0;D3;+0:7](=[O;D1;H0:8]):[c:5](:[c:6]):[c:3](:[c:4]):[#7;a:2](-[C;D1;H3:1]):[c;H0;D3;+0:9]:1=[O;D1;H0:10] | null | [] | null | null | 20 | HOUR | A mixture of 2.12 g of 4-chloro-N-methylisatoic anhydride, 1.39 g of 3-(1H-imidazol-1-yl)-2-methylpropanamine and 20 ml of ethanol was stirred at room temperature for 20 hours and concentrated. Ethyl chloroformate (10 ml) was added and the mixture was heated in an oil bath at 90°-105° C. for 2 hours, dissolved in ethan... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccc2cocnc2c1 | c1ccc2ncncc2c1 | c1c[nH]cn1.c1ccc2ncncc2c1 | HO- | C(C)O | null | 20 | CC(CN)Cn1ccnc1.Cn1c(=O)oc(=O)c2ccc(Cl)cc21>C(C)O>CC(Cn1ccnc1)Cn1c(=O)c2ccc(Cl)cc2n(C)c1=O |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7608171c4948438485513da06239373e | COc1ccc(CCl)cc1.NC(N)=S>>COc1ccc(CSC(=N)N)cc1.Cl | NC(=S)N.COC1=CC=C(CCl)C=C1>>Cl.COC1=CC=C(CSC(N)=N)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][Cl:14])[cH:12][cH:13]1.[S:8]=[C:9]([NH2:10])[NH2:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][C:9](=[NH:10])[NH2:11])[cH:12][cH:13]1.[ClH:14] | COc1ccc(CCl)cc1.NC(N)=S | COc1ccc(CSC(=N)N)cc1.Cl | null | null | O1CCCC1.CCOCC | Protection | OtherReaction | dae623ec10e42086cc0292009bc19d7d58877ce2428714b92cfbbb5102c39de2 | f72dba6c0cce6a796ff9aeda8637cc446706f96a34b889e05557c4a922c09746 | c1ccccc1 | [Cl;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5].[N;D1;H2:6]-[C;H0;D3;+0:7](-[NH2;D1;+0:8])=[S;H0;D1;+0:9]>>[ClH;D0;+0:1].[N;D1;H2:6]-[C;H0;D3;+0:7](=[NH;D1;+0:8])-[S;H0;D2;+0:9]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 93.8 | [{"value": 93.8, "product": "Cl.COC1=CC=C(CSC(N)=N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | A suspension of thiourea (38 g, 50.0 mmole) in dry tetrahydrofuran (40 ml) was cooled to 0° C. under argon and was treated dropwise with 4-methoxybenzylchloride (8.0 g, 50.0 mmole). After the addition was completed, the cooling bath was removed and the reaction was allowed to stir at room temperature for 2 hours. It wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Thiourea | Monosulfide | null | null | c1ccccc1 | null | O1CCCC1.CCOCC | 0 | 2 | COc1ccc(CCl)cc1.NC(N)=S>O1CCCC1.CCOCC>COc1ccc(CSC(=N)N)cc1.Cl |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e2cffd1c66054b768b80b231e6cef9d5 | COC(=O)C1=C(C)NC(SCc2ccc(OC)cc2)=NC1c1cccc([N+](=O)[O-])c1.CS(=O)(=O)Cl>>COC(=O)C1=C(C)N=C(SCc2ccc(OC)cc2)N(S(C)(=O)=O)C1c1cccc([N+](=O)[O-])c1 | COC1=CC=C(C=C1)CSC=1NC(=C(C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC)C.N1=CC=CC=C1.CS(=O)(=O)Cl>>COC1=CC=C(C=C1)CSC=1N(C(C(=C(N1)C)C(=O)OC)C1=CC(=CC=C1)[N+](=O)[O-])S(=O)(=O)C | [CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH3:7])[NH:8][C:9]([S:10][CH2:11][c:12]2[cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18][cH:19]2)=[N:20][CH:25]1[c:26]1[cH:27][cH:28][cH:29][c:30]([N+:31](=[O:32])[O-:33])[cH:34]1.Cl[S:21]([CH3:22])(=[O:23])=[O:24]>>[CH3:1][O:2][C:3](=[O:4])[C:5]1=[C:6]([CH3:7])[N:8]=[C:9]([S:10][CH2:1... | COC(=O)C1=C(C)NC(SCc2ccc(OC)cc2)=NC1c1cccc([N+](=O)[O-])c1.CS(=O)(=O)Cl | COC(=O)C1=C(C)N=C(SCc2ccc(OC)cc2)N(S(C)(=O)=O)C1c1cccc([N+](=O)[O-])c1 | null | null | ClCCl | Acylation | OtherReaction | d774f4d5227e112805087e03a9950a8f56e57cb1b78161dbcf43515d9fb2847f | 6f49fb3f924c02db804d372ae503350fdb5996766eb84c66c02a474596ce6076 | C1=CC(c2ccccc2)NC(SCc2ccccc2)=N1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1=[C:9](-[C;D1;H3:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12](-[#16:13]-[C:14])=[N;H0;D2;+0:15]-[C:16]-1-[c:17]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1=[C:9](-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D3;+0:12](-[#16:13]-[C:14])-[N;H0;D3;+0:15](-[S;H... | null | [] | null | null | 8 | HOUR | A solution of 1, 4-dihydro-2-[[(4-methoxyphenyl)methyl]thio-]6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, methyl ester (1.14 g, 2.66 mmole) in 15 ml of dichloromethane under argon at 0°-5° C. was treated with pyridine (0.42 ml, 0.42 g, 5.32 mmole) and methanesulfonyl chloride (0.28 ml, 0.41 g, 3.57 mmole). T... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Monosulfide.Sulfonyl halide | Tertiary amine.Monosulfide | C1=CNC=NC1 | C1=CN=C[NH]C1 | C1=CN=C[NH]C1.c1ccccc1.c1ccccc1 | HCl | ClCCl | null | 8 | COC(=O)C1=C(C)NC(SCc2ccc(OC)cc2)=NC1c1cccc([N+](=O)[O-])c1.CS(=O)(=O)Cl>ClCCl>COC(=O)C1=C(C)N=C(SCc2ccc(OC)cc2)N(S(C)(=O)=O)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0a47d9448359468d91c08b73c213d4f4 | CCOC(=O)C1=C(c2cccc([N+](=O)[O-])c2)N(S(=O)(=O)c2ccccc2)CN=C1C.CCS>>CCOC(=O)C1=C(C)NC(=S)N(S(=O)(=O)c2ccccc2)C1c1cccc([N+](=O)[O-])c1 | CC1=NCN(C(=C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])S(=O)(=O)C1=CC=CC=C1.FC(C(=O)O)(F)F.C(C)S>>CC1=C(C(N(C(N1)=S)S(=O)(=O)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:22]([c:23]2[cH:24][cH:25][cH:26][c:27]([N+:28](=[O:29])[O-:30])[cH:31]2)[N:12]([S:13](=[O:14])(=[O:15])[c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[CH2:10][N:9]=[C:7]1[CH3:8].CC[SH:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10](=[S:11])[N:12]([S:13](=[O:... | CCOC(=O)C1=C(c2cccc([N+](=O)[O-])c2)N(S(=O)(=O)c2ccccc2)CN=C1C.CCS | CCOC(=O)C1=C(C)NC(=S)N(S(=O)(=O)c2ccccc2)C1c1cccc([N+](=O)[O-])c1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | 7eda16852a284f2b7c138eab36c2a5129885f5f1d3858901950956e4111599ae | ff62f6bbddd259b8a8300c8263349c663414182ec129553508078639e4251d37 | O=S(=O)(c1ccccc1)N1C(=S)NC=CC1c1ccccc1 | C-C-[SH;D1;+0:1].[#16:2]-[#7:3]1-[CH2;D2;+0:4]-[N;H0;D2;+0:5]=[C;H0;D3;+0:6](-[C;D1;H3:7])-[C;H0;D3;+0:8](-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12])=[C;H0;D3;+0:13]-1-[c:14](:[c:15]):[c:16]>>[#16:2]-[#7:3]1-[C;H0;D3;+0:4](=[S;H0;D1;+0:1])-[NH;D2;+0:5]-[C;H0;D3;+0:6](-[C;D1;H3:7])=[C;H0;D3;+0:8](-[C:9](=[O;D1;H0:10])-[#8:11]... | null | [] | null | null | null | null | A solution of 0.95 g (0.0016 mole) of 1, 6-dihydro-2-[(4-methoxyphenyl)methyl]thio]-4-methyl -6-(3-nitrophenyl)-1-(phenylsulfonyl)-5pyrimidinecarboxylic acid, ethyl ester, 0.6 ml (0.0066 mole) of trifluoroacetic acid and 0.24 g (0.0037 mole) of ethanethiol in 20 ml of dichloromethane was stirred at room temperature ove... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ester.Substituted imine.Aliphatic thiol | Enamine.Ester.Thiourea | C1=C[NH]CN=C1 | C1=CNC[NH]C1 | C1=CNC[NH]C1.c1ccccc1.c1ccccc1 | Other | ClCCl | null | null | CCOC(=O)C1=C(c2cccc([N+](=O)[O-])c2)N(S(=O)(=O)c2ccccc2)CN=C1C.CCS>ClCCl>CCOC(=O)C1=C(C)NC(=S)N(S(=O)(=O)c2ccccc2)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0823753611834577b41a22c78ed917ba | CCCCS(=O)(=O)N1C(SCc2ccc(OC)cc2)=NC(C)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.CCS.O=C(O)C(F)(F)F>>CC(C)OC(C)C.CCCCS(=O)(=O)N1C(=S)NC(C)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | C(CCC)S(=O)(=O)N1C(=NC(=C(C1C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C)SCC1=CC=C(C=C1)OC.FC(C(=O)O)(F)F.C(C)S>>C(C)(C)OC(C)C.C(CCC)S(=O)(=O)N1C(NC(=C(C1C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C)=S | c1c[c:6]([CH2:1][S:17][C:16]2=[N:18][C:19]([CH3:20])=[C:21]([C:22](=[O:23])[O:24][CH2:25][CH3:26])[CH:27]([c:28]3[cH:29][cH:30][cH:31][c:32]([N+:33](=[O:34])[O-:35])[cH:36]3)[N:15]2[S:12]([CH2:11][CH2:10][CH2:9][CH3:8])(=[O:13])=[O:14])ccc1O[CH3:3].S[CH2:5][CH3:7].O[C:2](C(F)(F)F)=[O:4]>>[CH3:1][CH:2]([CH3:3])[O:4][CH:... | CCCCS(=O)(=O)N1C(SCc2ccc(OC)cc2)=NC(C)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.CCS.O=C(O)C(F)(F)F | CC(C)OC(C)C.CCCCS(=O)(=O)N1C(=S)NC(C)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | OtherReaction | 9a8465300700aab3d042dbc458b7d4f600a1a13a5269d767cc86da4a884c3888 | de7a0933bdcc8d0c57a6a8dd338a9fbbe02597f9fa65590b7245cdbf3e16869a | S=C1NC=CC(c2ccccc2)N1 | F-C(-F)(-F)-[C;H0;D3;+0:1](-O)=[O;H0;D1;+0:2].S-[CH2;D2;+0:3]-[C;D1;H3:4].[#16:5]-[#7:6]1-[C:7]-[C:8](-[C:9](-[#8:10])=[O;D1;H0:11])=[C:12](-[C;D1;H3:13])-[N;H0;D2;+0:14]=[C;H0;D3;+0:15]-1-[S;H0;D2;+0:16]-[CH2;D2;+0:17]-[c;H0;D3;+0:18]1:c:c:c(-O-[CH3;D1;+0:19]):c:c:1>>[#16:5]-[#7:6]1-[C:7]-[C:8](-[C:9](-[#8:10])=[O;D1;... | 106.8 | [{"value": 106.8, "product": "C(CCC)S(=O)(=O)N1C(NC(=C(C1C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 0.80 g (0.0014 mole) of 1-(Butylsulfonyl)-1, 6-dihydro-2-[[(4-methoxyphenyl) methyl]thio]-4-methyl-6-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester, 0.52 ml (0.0057 mole) of trifluoroacetic acid and 0.21 g (0.0032 mole) of ethanethiol in 15 ml of dichloromethane was stirred at room temperature f... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carboxylic acid.Ether.Aliphatic thiol.Monosulfide | Enamine.Ether.Thiourea | c1ccccc1.C1=CN=C[NH]C1 | C1=CNC[NH]C1 | C1=CNC[NH]C1.c1ccccc1 | HF | ClCCl | null | null | CCCCS(=O)(=O)N1C(SCc2ccc(OC)cc2)=NC(C)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1.CCS.O=C(O)C(F)(F)F>ClCCl>CC(C)OC(C)C.CCCCS(=O)(=O)N1C(=S)NC(C)=C(C(=O)OCC)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8a14e3b74aa24069842986a21c1ef285 | CCOC(=O)C1=C(C)NC(SCc2ccc(OC)cc2)=NC1c1cccc([N+](=O)[O-])c1.CS(=O)(=O)Cl>>CCOC(=O)C1=C(C)N=C(SCc2ccc(OC)cc2)N(S(C)(=O)=O)C1c1cccc([N+](=O)[O-])c1 | CS(=O)(=O)Cl.COC1=CC=C(C=C1)CSC=1NC(=C(C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C.N1=CC=CC=C1>>COC1=CC=C(C=C1)CSC=1N(C(C(=C(N1)C)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])S(=O)(=O)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([S:11][CH2:12][c:13]2[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][cH:20]2)=[N:21][CH:26]1[c:27]1[cH:28][cH:29][cH:30][c:31]([N+:32](=[O:33])[O-:34])[cH:35]1.Cl[S:22]([CH3:23])(=[O:24])=[O:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[N:9]=[C:... | CCOC(=O)C1=C(C)NC(SCc2ccc(OC)cc2)=NC1c1cccc([N+](=O)[O-])c1.CS(=O)(=O)Cl | CCOC(=O)C1=C(C)N=C(SCc2ccc(OC)cc2)N(S(C)(=O)=O)C1c1cccc([N+](=O)[O-])c1 | null | null | ClCCl | Acylation | OtherReaction | d774f4d5227e112805087e03a9950a8f56e57cb1b78161dbcf43515d9fb2847f | 6f49fb3f924c02db804d372ae503350fdb5996766eb84c66c02a474596ce6076 | C1=CC(c2ccccc2)NC(SCc2ccccc2)=N1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1=[C:9](-[C;D1;H3:10])-[NH;D2;+0:11]-[C;H0;D3;+0:12](-[#16:13]-[C:14])=[N;H0;D2;+0:15]-[C:16]-1-[c:17]>>[#8:5]-[C:6](=[O;D1;H0:7])-[C:8]1=[C:9](-[C;D1;H3:10])-[N;H0;D2;+0:11]=[C;H0;D3;+0:12](-[#16:13]-[C:14])-[N;H0;D3;+0:15](-[S;H... | 85.5 | [{"value": 85.5, "product": "COC1=CC=C(C=C1)CSC=1N(C(C(=C(N1)C)C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])S(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 2.0 g (0.0045 mole) of 1, 4-dihydro-2-[[(4-methoxyphenyl)methyl]thio]6-methyl-4-(3-nitrophenyl) -5-pyrimidinecarboxylic acid, ethyl ester (see example 2A) in 15 ml of dichloromethane containing 0.71 g (0.0090 mole) of pyridine was cooled to -10° C. and treated slowly with a solution of 0.62 g (0.0054 mole... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Monosulfide.Sulfonyl halide | Tertiary amine.Monosulfide | C1=CNC=NC1 | C1=CN=C[NH]C1 | C1=CN=C[NH]C1.c1ccccc1.c1ccccc1 | HCl | ClCCl | null | 8 | CCOC(=O)C1=C(C)NC(SCc2ccc(OC)cc2)=NC1c1cccc([N+](=O)[O-])c1.CS(=O)(=O)Cl>ClCCl>CCOC(=O)C1=C(C)N=C(SCc2ccc(OC)cc2)N(S(C)(=O)=O)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b73c5667a45b47e58a27aba3d593882d | CCOC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(C)=O.COC(=N)N>>CCOC(=O)C1=C(C)NC(OC)=NC1c1cccc([N+](=O)[O-])c1 | [N+](=O)([O-])C=1C=C(C=CC1)C=C(C(=O)OCC)C(C)=O.S(=O)(=O)(O)O.COC(N)=N.C([O-])(O)=O.[Na+]>>COC=1NC(=C(C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C | O=[C:7]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[CH:14][c:15]1[cH:16][cH:17][cH:18][c:19]([N+:20](=[O:21])[O-:22])[cH:23]1)[CH3:8].[NH2:9][C:10]([O:11][CH3:12])=[NH:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([O:11][CH3:12])=[N:13][CH:14]1[c:15]1[cH:16][cH:17][cH:18][c:19]([N+:20](=[O:21])[O-... | CCOC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(C)=O.COC(=N)N | CCOC(=O)C1=C(C)NC(OC)=NC1c1cccc([N+](=O)[O-])c1 | null | null | CN(C=O)C.C(C)(=O)OCC | Functional Group Addition | OtherReaction | 9f1202e283c567a005eda2f78f5cf6b8d5499a0601d061bbaa323632a00c4e55 | 236d42d1ec02a2fdb840ece71bec33a67ca67694e779d168e2cc0b28eec2fb71 | C1=CC(c2ccccc2)N=CN1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7])-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11].[#8:12]-[C:13](-[NH2;D1;+0:14])=[NH;D1;+0:15]>>[#8:12]-[C:13]1=[N;H0;D2;+0:15]-[CH;D3;+0:4](-[c:5](:[c:6]):[c:7])-[C;H0;D3;+0:3](-[C:8](=[O;D1;H0:9])-[#8:10]-[C:11])=[C;H0;D3;+0:1](-[C;D1;H3:2])-[NH;D2;+0... | 75.5 | [{"value": 75.5, "product": "COC=1NC(=C(C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A reaction mixture containing 2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid, ethyl ester (2.62 g, 10.0 mmole), O-methylpseudourea hydrogen sulfate (1.72 g, 10.0 mmole), and sodium bicarbonate (2.52 g, 30.0 mmole) in dimethylformamide (7 ml) was heated at 65°-70° C. for 16 hours. The reaction mixture was allowed to co... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Enamine.Ester | null | C1=CNC=NC1 | C1=CNC=NC1.c1ccccc1 | HO- | CN(C=O)C.C(C)(=O)OCC | null | null | CCOC(=O)C(=Cc1cccc([N+](=O)[O-])c1)C(C)=O.COC(=N)N>CN(C=O)C.C(C)(=O)OCC>CCOC(=O)C1=C(C)NC(OC)=NC1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-3f4149825a4443ebad2b17109bed7013 | CCOC(=O)C1=C(C)NC(OC)=NC1c1cccc([N+](=O)[O-])c1.O=S(=O)(Cl)c1ccccc1>>CCOC(=O)C1=C(C)NC(OC)N(S(=O)(=O)c2ccccc2)C1c1cccc([N+](=O)[O-])c1 | COC=1NC(=C(C(N1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C.C(C)N(CC)CC.C1(=CC=CC=C1)S(=O)(=O)Cl>>CC=1NC(N(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])S(=O)(=O)C1=CC=CC=C1)OC | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10]([O:11][CH3:12])=[N:13][CH:23]1[c:24]1[cH:25][cH:26][cH:27][c:28]([N+:29](=[O:30])[O-:31])[cH:32]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][cH:21][cH:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][CH:10]([O:11][CH3:12])[N:... | CCOC(=O)C1=C(C)NC(OC)=NC1c1cccc([N+](=O)[O-])c1.O=S(=O)(Cl)c1ccccc1 | CCOC(=O)C1=C(C)NC(OC)N(S(=O)(=O)c2ccccc2)C1c1cccc([N+](=O)[O-])c1 | null | null | ClCCl | Acylation | OtherReaction | 8be91f1c6b7ca5c67f7902f8ed4f6a969e14b8500b5556ede743bdfaa0ce083d | 0b8a98930f0260b0d069688155720a3b4fa2427af669d3b47d1fcd169f898772 | O=S(=O)(c1ccccc1)N1CNC=CC1c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]1=[C:11](-[C;D1;H3:12])-[#7:13]-[C;H0;D3;+0:14](-[#8:15]-[C;D1;H3:16])=[N;H0;D2;+0:17]-[C:18]-1-[c:19]>>[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]1=[C:11](-[C;D1;H3:12])-[#7:13]-[CH;D3;+0:14](-[#8:15]-[C;D1;H3:16])-[N;H0;D3;+0:17]... | 63.7 | [{"value": 63.7, "product": "CC=1NC(N(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])S(=O)(=O)C1=CC=CC=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 1, 4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl) -5-pyrimidinecarboxylic acid, ethyl ester (3.19 g, 10.0 mmole; see Example 5A) and distilled triethylamine (4.18 ml, 30.0 mmol) in distilled dichloromethane (20 ml) in an ice bath under argon was treated dropwise via syringe with benzenesulfonyl chloride (... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Sulfonyl halide | Ether.Tertiary amine | C1=CNC=NC1 | C1=CNC[NH]C1 | C1=CNC[NH]C1.c1ccccc1.c1ccccc1 | Other | ClCCl | null | 8 | CCOC(=O)C1=C(C)NC(OC)=NC1c1cccc([N+](=O)[O-])c1.O=S(=O)(Cl)c1ccccc1>ClCCl>CCOC(=O)C1=C(C)NC(OC)N(S(=O)(=O)c2ccccc2)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c8cc252a4d154990bb69632f1a9aae94 | CCOC(=O)C1=C(C)NC(OC)N(S(=O)(=O)c2ccccc2)C1c1cccc([N+](=O)[O-])c1>>CCOC(=O)C1=C(C)NC(=O)N(S(=O)(=O)c2ccccc2)C1c1cccc([N+](=O)[O-])c1 | CC=1NC(N(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])S(=O)(=O)C1=CC=CC=C1)OC.Cl>>CC=1NC(N(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])S(=O)(=O)C1=CC=CC=C1)=O | C[O:11][CH:10]1[NH:9][C:7]([CH3:8])=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:22]([c:23]2[cH:24][cH:25][cH:26][c:27]([N+:28](=[O:29])[O-:30])[cH:31]2)[N:12]1[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1=[C:7]([CH3:8])[NH:9][C:10](=[O:11])[N:12]([S:13](=[O:1... | CCOC(=O)C1=C(C)NC(OC)N(S(=O)(=O)c2ccccc2)C1c1cccc([N+](=O)[O-])c1 | CCOC(=O)C1=C(C)NC(=O)N(S(=O)(=O)c2ccccc2)C1c1cccc([N+](=O)[O-])c1 | null | null | O1C(CCC1)CO | Miscellaneous | OtherReaction | 0b2e9e49f793787d22b531203f998c52670ae738273347c109c1114acb510e78 | c8ccc36975b15092630c11669b3ab3698aeb0825586ea408ba8aa6627541cd1e | O=C1NC=CC(c2ccccc2)N1S(=O)(=O)c1ccccc1 | C-[O;H0;D2;+0:1]-[CH;D3;+0:2]1-[#7:3]-[C:4](-[C;D1;H3:5])=[C:6](-[C:7](-[#8:8])=[O;D1;H0:9])-[C:10]-[#7:11]-1-[#16:12]>>[#16:12]-[#7:11]1-[C:10]-[C:6](-[C:7](-[#8:8])=[O;D1;H0:9])=[C:4](-[C;D1;H3:5])-[#7:3]-[C;H0;D3;+0:2]-1=[O;H0;D1;+0:1] | 40.8 | [{"value": 40.8, "product": "CC=1NC(N(C(C1C(=O)OCC)C1=CC(=CC=C1)[N+](=O)[O-])S(=O)(=O)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 1, 2, 3, 6-tetrahydro-4-methyl-6-(3-nitrophenyl)-2-methoxy-1-(phenylsulfonyl)-5 -pyrimidinecarboxylic acid, ethyl ester (1.49 g, 3.24 mmol) in tetrahydrofuran-methanol (20 ml each) was treated with 5N hydrochloric acid (5.0 ml) and stirred at room temperature overnight. The reaction mixture was evaporated... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Urea | C1=CNC[NH]C1 | C1=CNC[NH]C1 | C1=CNC[NH]C1.c1ccccc1.c1ccccc1 | Other | O1C(CCC1)CO | null | 8 | CCOC(=O)C1=C(C)NC(OC)N(S(=O)(=O)c2ccccc2)C1c1cccc([N+](=O)[O-])c1>O1C(CCC1)CO>CCOC(=O)C1=C(C)NC(=O)N(S(=O)(=O)c2ccccc2)C1c1cccc([N+](=O)[O-])c1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b2a1885435394c86a9ae7fb2a5c46883 | O=C(c1ccc(F)cc1)N1CCNCC1.O=S(=O)(Cl)c1ccc(Nc2ccnc3cc(C(F)(F)F)ccc23)cc1>>O=C(c1ccc(F)cc1)N1CCN(S(=O)(=O)c2ccc(Nc3ccnc4cc(C(F)(F)F)ccc34)cc2)CC1 | Cl.FC(C1=CC=C2C(=CC=NC2=C1)NC1=CC=C(C=C1)S(=O)(=O)Cl)(F)F.Cl.FC1=CC=C(C(=O)N2CCNCC2)C=C1.C([O-])([O-])=O.[Na+].[Na+]>>FC1=CC=C(C(=O)N2CCN(CC2)S(=O)(=O)C2=CC=C(C=C2)NC2=CC=NC3=CC(=CC=C23)C(F)(F)F)C=C1 | [O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[N:10]1[CH2:11][CH2:12][NH:13][CH2:38][CH2:39]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][c:20]([NH:21][c:22]2[cH:23][cH:24][n:25][c:26]3[cH:27][c:28]([C:29]([F:30])([F:31])[F:32])[cH:33][cH:34][c:35]23)[cH:36][cH:37]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F... | O=C(c1ccc(F)cc1)N1CCNCC1.O=S(=O)(Cl)c1ccc(Nc2ccnc3cc(C(F)(F)F)ccc23)cc1 | O=C(c1ccc(F)cc1)N1CCN(S(=O)(=O)c2ccc(Nc3ccnc4cc(C(F)(F)F)ccc34)cc2)CC1 | null | null | O.C(Cl)(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | c6a995ab9be6571957febbe378833244177e30fd671e64e4e1ffe6f50345cf56 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(c1ccccc1)N1CCN(S(=O)(=O)c2ccc(Nc3ccnc4ccccc34)cc2)CC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:4](:[c:5]):[c:6] | 20.1 | [{"value": 20.1, "product": "FC1=CC=C(C(=O)N2CCN(CC2)S(=O)(=O)C2=CC=C(C=C2)NC2=CC=NC3=CC(=CC=C23)C(F)(F)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-(7-Trifluoromethyl-4-quinolinylamino)benzenesulphonyl chloride hydrochloride (3.5 g, 0.008 mol) was added portionwise to a cold (10°), well stirred mixture of 1-(4-fluorobenzoyl)piperazine hydrochloride (2.0 g, 0.008 mol) in chloroform (50 ml) and sodium carbonate (10.0 g) in water (50 ml). The cooling bath was remov... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccc2ncccc2c1 | HCl | O.C(Cl)(Cl)Cl | null | null | O=C(c1ccc(F)cc1)N1CCNCC1.O=S(=O)(Cl)c1ccc(Nc2ccnc3cc(C(F)(F)F)ccc23)cc1>O.C(Cl)(Cl)Cl>O=C(c1ccc(F)cc1)N1CCN(S(=O)(=O)c2ccc(Nc3ccnc4cc(C(F)(F)F)ccc34)cc2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-53574dbaa76f4e1ea1aa1fc0780d1a5b | O=C(c1ccc(F)cc1)N1CCNCC1.O=S(=O)(Cl)c1ccc(Nc2ccnc3cc(Cl)ccc23)cc1>>O=C(c1ccc(F)cc1)N1CCN(S(=O)(=O)c2ccc(Nc3ccnc4cc(Cl)ccc34)cc2)CC1 | Cl.FC1=CC=C(C(=O)N2CCNCC2)C=C1.C([O-])([O-])=O.[Na+].[Na+].Cl.ClC1=CC=C2C(=CC=NC2=C1)NC1=CC=C(C=C1)S(=O)(=O)Cl>>ClC1=CC=C2C(=CC=NC2=C1)NC1=CC=C(C=C1)S(=O)(=O)N1CCN(CC1)C(C1=CC=C(C=C1)F)=O | [O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[N:10]1[CH2:11][CH2:12][NH:13][CH2:35][CH2:36]1.Cl[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][c:20]([NH:21][c:22]2[cH:23][cH:24][n:25][c:26]3[cH:27][c:28]([Cl:29])[cH:30][cH:31][c:32]23)[cH:33][cH:34]1>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([F:7])[cH:8][cH:9]1)[N:... | O=C(c1ccc(F)cc1)N1CCNCC1.O=S(=O)(Cl)c1ccc(Nc2ccnc3cc(Cl)ccc23)cc1 | O=C(c1ccc(F)cc1)N1CCN(S(=O)(=O)c2ccc(Nc3ccnc4cc(Cl)ccc34)cc2)CC1 | null | null | O.C(Cl)(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | c6a995ab9be6571957febbe378833244177e30fd671e64e4e1ffe6f50345cf56 | b7aca5a5d690b0846685a854bc946849e1041bfc3965161290b5ffb2821af09e | O=C(c1ccccc1)N1CCN(S(=O)(=O)c2ccc(Nc3ccnc4ccccc34)cc2)CC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[O;D1;H0:2]=[S;H0;D4;+0:1](=[O;D1;H0:3])(-[N;H0;D3;+0:10]1-[C:9]-[C:8]-[#7:7]-[C:12]-[C:11]-1)-[c:4](:[c:5]):[c:6] | 5 | [{"value": 5.0, "product": "ClC1=CC=C2C(=CC=NC2=C1)NC1=CC=C(C=C1)S(=O)(=O)N1CCN(CC1)C(C1=CC=C(C=C1)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-(7-Chloro-4-quinolinylamino)benzenesulphonyl chloride hydrochloride (7.8 g, 0.02 mol) was added portionwise with stirring to a cold mixture of 1-(4-fluorobenzoyl)piperazine hydrochloride (4.9 g, 0.02 mol) in chloroform (250 ml) and sodium carbonate (24.4 g) in water (250 ml). The cooling bath was removed and the mixt... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Sulfonyl halide | Tertiary amine | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccc2ncccc2c1 | HCl | O.C(Cl)(Cl)Cl | null | null | O=C(c1ccc(F)cc1)N1CCNCC1.O=S(=O)(Cl)c1ccc(Nc2ccnc3cc(Cl)ccc23)cc1>O.C(Cl)(Cl)Cl>O=C(c1ccc(F)cc1)N1CCN(S(=O)(=O)c2ccc(Nc3ccnc4cc(Cl)ccc34)cc2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-dcd3725c96a04a9593a84eede8dd596e | O=C(c1ccc(F)cc1)N1CCNCC1.O=[N+]([O-])c1ccc(S(=O)(=O)Cl)cc1>>Nc1ccc(S(=O)(=O)N2CCN(C(=O)c3ccc(F)cc3)CC2)cc1.O=C(c1ccc(F)cc1)N1CCN(S(=O)(=O)c2ccc([N+](=O)[O-])cc2)CC1 | [H][H].[N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)Cl.Cl.FC1=CC=C(C(=O)N2CCNCC2)C=C1>>FC1=CC=C(C(=O)N2CCN(CC2)S(=O)(=O)C2=CC=C(C=C2)[N+](=O)[O-])C=C1.NC1=CC=C(C=C1)S(=O)(=O)N1CCN(CC1)C(C1=CC=C(C=C1)F)=O | [NH:1]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[c:15]2[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]2)[CH2:22][CH2:23]1.Cl[S:6]([c:5]1[cH:4][cH:2][c:45]([N+:46](=[O:47])[O-:48])[cH:49][cH:33]1)(=[O:7])=[O:8]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[N:9]2[CH2:10][CH2:11][N:12]([C:13](=[O:14])[c:15]3[cH:16][cH:17]... | O=C(c1ccc(F)cc1)N1CCNCC1.O=[N+]([O-])c1ccc(S(=O)(=O)Cl)cc1 | Nc1ccc(S(=O)(=O)N2CCN(C(=O)c3ccc(F)cc3)CC2)cc1.O=C(c1ccc(F)cc1)N1CCN(S(=O)(=O)c2ccc([N+](=O)[O-])cc2)CC1 | null | null | C(C)O | Aromatic Heterocycle Formation | Sulfonamide synthesis (Schotten-Baumann) secondary amine | 74d64146bf52426b27f8bb455f47e27c54a6a2ed22a9262dd4ad836849399722 | e83835a097b7a396536abb238f1d6ae1185ad803c87dfd904fe527fd421a7c0f | O=C(c1ccccc1)N1CCN(S(=O)(=O)c2ccccc2)CC1.O=C(c1ccccc1)N1CCN(S(=O)(=O)c2ccccc2)CC1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[#7;+:8](-[O;-;D1;H0:9])=[O;D1;H0:10]):[cH;D2;+0:11]:[cH;D2;+0:12]:1.[O;D1;H0:13]=[C:14]-[#7:15]1-[C:16]-[CH2;D2;+0:17]-[NH;D2;+0:18]-[CH2;D2;+0:19]-[C:20]-1>>[F;D1;H0:21]-[c:22](:[c:23]):[cH;D2;+0:5]:[c:24]:[c:25].[... | null | [] | null | null | null | null | 1-(4-fluorobenzoyl)-4-(4-nitrobenzenesulphonyl)piperazine is prepared in a similar manner to Examples 1 and 2 by reacting equimolar quantities of 4-nitrobenzenesulphonyl chloride with 1-(4-fluorobenzoyl)piperazine hydrochloride. The reaction product is hydrogenated in ethanol at room temperature at atmospheric pressure... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Secondary amine.Sulfonyl halide | Aromatic halide.Nitro group.Tertiary amide.Primary amine.Tertiary amine.Tertiary amine | C1CNCC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccccc1 | null | C(C)O | null | null | O=C(c1ccc(F)cc1)N1CCNCC1.O=[N+]([O-])c1ccc(S(=O)(=O)Cl)cc1>C(C)O>Nc1ccc(S(=O)(=O)N2CCN(C(=O)c3ccc(F)cc3)CC2)cc1.O=C(c1ccc(F)cc1)N1CCN(S(=O)(=O)c2ccc([N+](=O)[O-])cc2)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-21b027930e4e4e02ae9de412f59b679b | Cc1cnc(Sc2ccc([N+](=O)[O-])cc2)c(C#N)c1.O=C1CCC(=O)N1Br>>N#Cc1cc(CBr)cnc1Sc1ccc([N+](=O)[O-])cc1 | C(#N)C=1C(=NC=C(C1)C)SC1=CC=C(C=C1)[N+](=O)[O-].BrN1C(CCC1=O)=O.C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O>>C(#N)C=1C(=NC=C(C1)CBr)SC1=CC=C(C=C1)[N+](=O)[O-] | [N:1]#[C:2][c:3]1[cH:4][c:5]([CH3:6])[cH:8][n:9][c:10]1[S:11][c:12]1[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1.O=C1CCC(=O)N1[Br:7]>>[N:1]#[C:2][c:3]1[cH:4][c:5]([CH2:6][Br:7])[cH:8][n:9][c:10]1[S:11][c:12]1[cH:13][cH:14][c:15]([N+:16](=[O:17])[O-:18])[cH:19][cH:20]1 | Cc1cnc(Sc2ccc([N+](=O)[O-])cc2)c(C#N)c1.O=C1CCC(=O)N1Br | N#Cc1cc(CBr)cnc1Sc1ccc([N+](=O)[O-])cc1 | null | null | C1=CC=CC=C1 | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccc(Sc2ccccn2)cc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | null | [] | null | null | null | null | A mixture of 60.00 g (0.221 mol) of 3-cyano-2-(4-nitrophenylthio)-5-methylpyridine, 39.37 g (0.221 mol) of N-bromosuccinimide, 3.0 g of benzoyl peroxide and 60 mL of benzene was refluxed for 16 hours while being irradiated with a 275-W sunlamp. The solvent was removed under reduced pressure and the residue was shaken w... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccncc1.c1ccccc1 | HO- | C1=CC=CC=C1 | null | null | Cc1cnc(Sc2ccc([N+](=O)[O-])cc2)c(C#N)c1.O=C1CCC(=O)N1Br>C1=CC=CC=C1>N#Cc1cc(CBr)cnc1Sc1ccc([N+](=O)[O-])cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-30c38e6c44134c8aa3772aafb891d2a6 | CCCCP(CCCC)CCCC.N#Cc1cc(CBr)cnc1Sc1ccc([N+](=O)[O-])cc1>>CCCC[P+](CCCC)(CCCC)Cc1cnc(Sc2ccc([N+](=O)[O-])cc2)c(C#N)c1.[Br-] | C(CCC)P(CCCC)CCCC.C(#N)C=1C(=NC=C(C1)CBr)SC1=CC=C(C=C1)[N+](=O)[O-].CCOCC>>[Br-].C(#N)C=1C(=NC=C(C1)C[P+](CCCC)(CCCC)CCCC)SC1=CC=C(C=C1)[N+](=O)[O-] | [CH3:1][CH2:2][CH2:3][CH2:4][P:5]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13].[CH2:14]([c:15]1[cH:16][n:17][c:18]([S:19][c:20]2[cH:21][cH:22][c:23]([N+:24](=[O:25])[O-:26])[cH:27][cH:28]2)[c:29]([C:30]#[N:31])[cH:32]1)[Br:33]>>[CH3:1][CH2:2][CH2:3][CH2:4][P+:5]([CH2:6][CH2:7][CH2:8][CH3:9])([CH2:10][C... | CCCCP(CCCC)CCCC.N#Cc1cc(CBr)cnc1Sc1ccc([N+](=O)[O-])cc1 | CCCC[P+](CCCC)(CCCC)Cc1cnc(Sc2ccc([N+](=O)[O-])cc2)c(C#N)c1.[Br-] | null | null | O1CCCC1 | Functional Group Interconversion | OtherReaction | 72a5231b07f184f0ef4a0648badd4176f521b95f1ba3340a0f90d8894af47260 | 47a659f5704a5b7ca1b92ff731f18f109c6bde1d45152a3a393eefbd10265508 | c1ccc(Sc2ccccn2)cc1 | [Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7].[C:8]-[C:9]-[P;H0;D3;+0:10](-[C:11]-[C:12])-[C:13]-[C:14]>>[Br-;H0;D0:1].[C:8]-[C:9]-[P+;H0;D4:10](-[C:11]-[C:12])(-[C:13]-[C:14])-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | null | [] | null | null | null | null | Alternatively, 3-cyano-2-(4-nitrophenylthio)-5-bromomethylpyridine is allowed to react in tetrahydrofuran with tri-(n-butyl)phosphine for ten hours. Following the addition of ether, the solid which forms is collected by filtration and washed with 1:1 tetrahydrofuran:ether to yield [3-cyano-2-(4-nitrophenylthio)pyridin-... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | null | null | c1ccncc1.c1ccccc1 | null | O1CCCC1 | null | null | CCCCP(CCCC)CCCC.N#Cc1cc(CBr)cnc1Sc1ccc([N+](=O)[O-])cc1>O1CCCC1>CCCC[P+](CCCC)(CCCC)Cc1cnc(Sc2ccc([N+](=O)[O-])cc2)c(C#N)c1.[Br-] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f808c9d44a7243339f16cbc8a848aca3 | CCOC(=O)c1ccc(C=O)cc1.N#Cc1cc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cnc1Sc1ccc([N+](=O)[O-])cc1>>CCOC(=O)c1ccc(C=Cc2cnc(Sc3ccc([N+](=O)[O-])cc3)c(C#N)c2)cc1 | C(C)OC(=O)C1=CC=C(C=O)C=C1.[Br-].C(#N)C=1C(=NC=C(C1)C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)SC1=CC=C(C=C1)[N+](=O)[O-].C(C)N(CC)CC.C(Cl)(Cl)Cl>>C(#N)C=1C(=NC=C(C1)C=CC1=CC=C(C=C1)C(=O)OCC)SC1=CC=C(C=C1)[N+](=O)[O-] | O=[CH:10][c:9]1[cH:8][cH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:31][cH:30]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:11][c:12]2[cH:13][n:14][c:15]([S:16][c:17]3[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][cH:25]3)[c:26]([C:27]#[N:28])[cH:29]2)cc1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH:10]=... | CCOC(=O)c1ccc(C=O)cc1.N#Cc1cc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cnc1Sc1ccc([N+](=O)[O-])cc1 | CCOC(=O)c1ccc(C=Cc2cnc(Sc3ccc([N+](=O)[O-])cc3)c(C#N)c2)cc1 | null | null | O | C-C Coupling | Wittig with Phosphonium | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | C(=Cc1ccc(Sc2ccccc2)nc1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[c:5]:[#7;a:6]:[c:7]:[c:8](-[CH2;D2;+0:9]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:10]>>[c:5]:[#7;a:6]:[c:7]:[c:8](-[CH;D2;+0:9]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]):[c:10] | 88.1 | [{"value": 88.0, "product": "C(#N)C=1C(=NC=C(C1)C=CC1=CC=C(C=C1)C(=O)OCC)SC1=CC=C(C=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.1, "product": "C(#N)C=1C(=NC=C(C1)C=CC1=CC=C(C=C1)C(=O)OCC)SC1=CC=C(C=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | A mixture of 4.544 g (7.42 mmol) of [3-cyano-2-(4-nitrophenylthio)-5-pyridinylmethyl]triphenylphosphonium bromide, 0.751 g (7.42 mmol) of triethylamine and 50 mL of chloroform was stirred at room temperature for 15 minutes and 1.322 g (7.42 mmol) of 4-ethoxycarbonylbenzaldehyde then were added. After stirring at room t... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1ccccc1.c1ccncc1.c1ccccc1 | HO- | O | null | 0.25 | CCOC(=O)c1ccc(C=O)cc1.N#Cc1cc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cnc1Sc1ccc([N+](=O)[O-])cc1>O>CCOC(=O)c1ccc(C=Cc2cnc(Sc3ccc([N+](=O)[O-])cc3)c(C#N)c2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-85efc50b27c147778ee85f5704637344 | CC(C)(C)OC(=O)c1ccc(C=Cc2cnc(N)c(C#N)c2)cc1>>CCOC(=O)c1ccc(C=Cc2cnc(N)c(C#N)c2)cc1 | NC1=NC=C(C=C1C#N)C=CC1=CC=C(C=C1)C(=O)OC(C)(C)C.[K+].[Br-]>>NC1=NC=C(C=C1C#N)C=CC1=CC=C(C=C1)C(=O)OCC | C[C:2](C)([CH3:1])[O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH:10]=[CH:11][c:12]2[cH:13][n:14][c:15]([NH2:16])[c:17]([C:18]#[N:19])[cH:20]2)[cH:21][cH:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH:10]=[CH:11][c:12]2[cH:13][n:14][c:15]([NH2:16])[c:17]([C:18]#[N:19])[cH:20]2)[cH:21][cH:22]1 | CC(C)(C)OC(=O)c1ccc(C=Cc2cnc(N)c(C#N)c2)cc1 | CCOC(=O)c1ccc(C=Cc2cnc(N)c(C#N)c2)cc1 | null | null | null | Miscellaneous | OtherReaction | 65c8f61c086a235ce6692c51186a0187b2fa4d47add33293a3d7824255d1a4bf | 019584698d6f4e780dc33c58bbe427f505956c44d516240fec11049769c33a01 | C(=Cc1cccnc1)c1ccccc1 | C-[C;H0;D4;+0:1](-C)(-[C;D1;H3:2])-[#8:3]-[C:4](=[O;D1;H0:5])-[c:6]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[#8:3]-[C:4](=[O;D1;H0:5])-[c:6] | null | [] | null | null | null | null | By substituting an equivalent amount of 3-cyano-2-(4-nitrophenylthio)-5-[2-(4-tert-butoxycarbonylphenyl)ethenyl]pyridine in the foregoing procedure there is obtained 2-amino-3-cyano-5-[2-(4-tert-butoxycarbonylphenyl)ethenyl]pyridine, which can be alternatively named as 2-amino-3-cyano-5-(4-t-butoxycarbonylstyryl)pyridi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Ester | null | null | c1ccccc1.c1ccncc1 | Other | null | null | null | CC(C)(C)OC(=O)c1ccc(C=Cc2cnc(N)c(C#N)c2)cc1>>CCOC(=O)c1ccc(C=Cc2cnc(N)c(C#N)c2)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-018ed512f3da4cfab0d1e91783c4353e | CC(C)(C)OC(=O)c1ccc(C=Cc2cnc3nc(N)nc(N)c3c2)cc1>>Nc1nc(N)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 | NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)OC(C)(C)C)N>>NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)O)N | CC(C)(C)[O:17][C:15]([c:14]1[cH:13][cH:12][c:11]([CH:10]=[CH:9][c:8]2[cH:7][c:6]3[c:4]([NH2:5])[n:3][c:2]([NH2:1])[n:23][c:22]3[n:21][cH:20]2)[cH:19][cH:18]1)=[O:16]>>[NH2:1][c:2]1[n:3][c:4]([NH2:5])[c:6]2[cH:7][c:8]([CH:9]=[CH:10][c:11]3[cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]3)[cH:20][n:21][c:22]2[n... | CC(C)(C)OC(=O)c1ccc(C=Cc2cnc3nc(N)nc(N)c3c2)cc1 | Nc1nc(N)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 | null | null | C(=O)O | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | C(=Cc1cnc2ncncc2c1)c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 79.1 | [{"value": 79.0, "product": "NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.1, "product": "NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 1.27 g of 2,4-diamino-6-[2-(4-tert-butoxycarbonylphenyl)ethenyl]pyrido[2,3-d]pyrimidine and 10 mL 88% formic acid was stirred at room temperature. A yellow solid started to form after about 12 hours and after 4 days of stirring, the reaction mixture was filtered. The collected solid was washed well succes... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1cnc2ncncc2c1.c1ccccc1 | Other | C(=O)O | null | null | CC(C)(C)OC(=O)c1ccc(C=Cc2cnc3nc(N)nc(N)c3c2)cc1>C(=O)O>Nc1nc(N)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-fb7f05d2e7a644bd8b0ce336ca093a0a | CC(C)(C)OC(=O)c1ccc(C=Cc2cnc3nc(N)nc(N)c3c2)cc1>>Nc1nc(N)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 | NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)OC(C)(C)C)N.Cl.CCOCC>>NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)O)N | CC(C)(C)[O:17][C:15]([c:14]1[cH:13][cH:12][c:11]([CH:10]=[CH:9][c:8]2[cH:7][c:6]3[c:4]([NH2:5])[n:3][c:2]([NH2:1])[n:23][c:22]3[n:21][cH:20]2)[cH:19][cH:18]1)=[O:16]>>[NH2:1][c:2]1[n:3][c:4]([NH2:5])[c:6]2[cH:7][c:8]([CH:9]=[CH:10][c:11]3[cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]3)[cH:20][n:21][c:22]2[n... | CC(C)(C)OC(=O)c1ccc(C=Cc2cnc3nc(N)nc(N)c3c2)cc1 | Nc1nc(N)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 | null | null | [N+](=O)([O-])C | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | C(=Cc1cnc2ncncc2c1)c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | Alternatively, 0.48 g of 2,4-diamino-6-[2-(4-tert-butoxycarbonylphenyl)ethenyl]pyrido[2,3-d]pyrimidine was added to a saturated solution of hydrogen chloride in 20 mL of nitromethane at 0°. The reaction mixture quickly became viscous and turned a deep yellow color and after a few minutes of stirring, a granular solid f... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1cnc2ncncc2c1.c1ccccc1 | Other | [N+](=O)([O-])C | null | null | CC(C)(C)OC(=O)c1ccc(C=Cc2cnc3nc(N)nc(N)c3c2)cc1>[N+](=O)([O-])C>Nc1nc(N)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-213276de92dc49d8b39311708cbdc79a | CC(=Cc1cnc2nc(N)nc(N)c2c1)c1ccc(C(=O)OC(C)(C)C)cc1>>CC(=Cc1cnc2nc(N)nc(N)c2c1)c1ccc(C(=O)O)cc1 | NC=1N=C(C2=C(N1)N=CC(=C2)C=C(C)C2=CC=C(C=C2)C(=O)OC(C)(C)C)N.Cl>>NC=1N=C(C2=C(N1)N=CC(=C2)C=C(C)C2=CC=C(C=C2)C(=O)O)N | CC(C)(C)[O:22][C:20]([c:19]1[cH:18][cH:17][c:16]([C:2]([CH3:1])=[CH:3][c:4]2[cH:5][n:6][c:7]3[n:8][c:9]([NH2:10])[n:11][c:12]([NH2:13])[c:14]3[cH:15]2)[cH:24][cH:23]1)=[O:21]>>[CH3:1][C:2](=[CH:3][c:4]1[cH:5][n:6][c:7]2[n:8][c:9]([NH2:10])[n:11][c:12]([NH2:13])[c:14]2[cH:15]1)[c:16]1[cH:17][cH:18][c:19]([C:20](=[O:21])... | CC(=Cc1cnc2nc(N)nc(N)c2c1)c1ccc(C(=O)OC(C)(C)C)cc1 | CC(=Cc1cnc2nc(N)nc(N)c2c1)c1ccc(C(=O)O)cc1 | null | null | [N+](=O)([O-])C | Deprotection | Deprotection of carboxylic acid | 152e5537e48c95b4a3e767536b0f9f68d1308e5f484070828ab5ed951805157a | 7f019d4cfe9b3036d0a2d3a3209aa0e1fcb05418ebee15a4be5e125d315d5f01 | C(=Cc1cnc2ncncc2c1)c1ccccc1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 100 | [{"value": 100.0, "product": "NC=1N=C(C2=C(N1)N=CC(=C2)C=C(C)C2=CC=C(C=C2)C(=O)O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.0, "product": "NC=1N=C(C2=C(N1)N=CC(=C2)C=C(C)C2=CC=C(C=C2)C(=O)O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | A suspension containing 4.58 g of 2,4-diamino-6-[2-(4-tert-butoxycarbonylphenyl)prop-1-enyl]pyrido[2,3-d]pyrimidine in 200 mL of a saturated solution of hydrogen chloride gas in nitromethane was stirred at 0° C. for 1 hour, and then at room temperature for 3 hours. After dilution with ether, the reaction mixture was fi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Boc | Carboxylic acid | null | null | c1cnc2ncncc2c1.c1ccccc1 | Other | [N+](=O)([O-])C | 0 | 1 | CC(=Cc1cnc2nc(N)nc(N)c2c1)c1ccc(C(=O)OC(C)(C)C)cc1>[N+](=O)([O-])C>CC(=Cc1cnc2nc(N)nc(N)c2c1)c1ccc(C(=O)O)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4e81c798b862450ba203c6d390f30e54 | CC(=O)O.Nc1nc(N)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1>>Nc1nc(O)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 | NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)O)N.C(C)(=O)O>>NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)O)O | CC(=O)[OH:5].N[c:4]1[n:3][c:2]([NH2:1])[n:23][c:22]2[c:6]1[cH:7][c:8]([CH:9]=[CH:10][c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]1)[cH:20][n:21]2>>[NH2:1][c:2]1[n:3][c:4]([OH:5])[c:6]2[cH:7][c:8]([CH:9]=[CH:10][c:11]3[cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]3)[cH:20][n:21][c:22]2[n:... | CC(=O)O.Nc1nc(N)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 | Nc1nc(O)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 | null | null | [OH-].[Na+] | Heteroatom Alkylation and Arylation | OtherReaction | 7ca64b4be7d9b4e636d504b0b83a77b8696a30dfcaa3255252a77bb0af6aaec4 | c3d157cb80ffcf8f3735e539a280b8e5b17dd9d465bb1854ed653f8cfcc0f054 | C(=Cc1cnc2ncncc2c1)c1ccccc1 | C-C(=O)-[OH;D1;+0:1].N-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[#7;a:7]:[c:8]):[c:9]:1:[c:10]>>[OH;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[#7;a:7]:[c:8]):[c:9]:1:[c:10] | 88 | [{"value": 88.0, "product": "NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of 1.0 g of 2,4-diamino-6-[2-(4-carboxyphenyl)ethenyl]pyrido[2,3-d]pyrimidine in 30 mL of 1N aqueous sodium hydroxide was heated under reflux under nitrogen for 3 hours. The resulting homogeneous orange solution was cooled to room temperature, acidified with 6 mL of glacial acetic acid, and the resulting y... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Aromatic alcohol | c1cnc2ncncc2c1 | c1cnc2ncncc2c1 | c1cnc2ncncc2c1.c1ccccc1 | HO- | [OH-].[Na+] | null | null | CC(=O)O.Nc1nc(N)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1>[OH-].[Na+]>Nc1nc(O)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-d54d129ce1c1497eb9fef7a3ec4df149 | CC(=Cc1cnc2nc(N)nc(O)c2c1)c1ccc(C(=O)O)cc1>>Nc1nc(O)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 | NC=1N=C(C2=C(N1)N=CC(=C2)C=C(C)C2=CC=C(C=C2)C(=O)O)N.NC=1N=C(C2=C(N1)N=CC(=C2)C=C(C)C2=CC=C(C=C2)C(=O)O)O>>NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)O)O | C[C:10](=[CH:9][c:8]1[cH:7][c:6]2[c:4]([OH:5])[n:3][c:2]([NH2:1])[n:23][c:22]2[n:21][cH:20]1)[c:11]1[cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]1>>[NH2:1][c:2]1[n:3][c:4]([OH:5])[c:6]2[cH:7][c:8]([CH:9]=[CH:10][c:11]3[cH:12][cH:13][c:14]([C:15](=[O:16])[OH:17])[cH:18][cH:19]3)[cH:20][n:21][c:22]2[n:23]1 | CC(=Cc1cnc2nc(N)nc(O)c2c1)c1ccc(C(=O)O)cc1 | Nc1nc(O)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C(=Cc1cnc2ncncc2c1)c1ccccc1 | C-[C;H0;D3;+0:1](=[C:2]-[c:3]:[c:4]:[#7;a:5])-[c:6](:[c:7]):[c:8]>>[#7;a:5]:[c:4]:[c:3]-[C:2]=[CH;D2;+0:1]-[c:6](:[c:7]):[c:8] | null | [] | null | null | null | null | In a similar fashion, 2,4-diamino-6-[2-(4-carboxyphenyl)prop-1-enyl]pyrido[2,3-d]pyrimidine is converted to 2-amino-4-hydroxy-6-[2-(4-carboxyphenyl)prop-1-enyl]pyrido[2,3-d]pyrimidine, mp >250° C.; NMR (DMSO-d6, 80 MHz) d 2.28 and 2.30 (brs, 3H), 6.77 and 7.06 (brs, 1H), 7.72 (d, 2H, J=8.5 Hz), 7.97 (d, 2H, J=8.5 Hz), ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1cnc2ncncc2c1.c1ccccc1 | Other | null | null | null | CC(=Cc1cnc2nc(N)nc(O)c2c1)c1ccc(C(=O)O)cc1>>Nc1nc(O)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-b960972cd72e46fd9bd32d0bf7382f1e | CC(=O)OC(C)=O.Nc1nc(O)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1>>CC(=O)Nc1nc(O)c2cc(C=Cc3ccc(C(=O)OC(C)=O)cc3)cnc2n1 | NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)O)O.C(C)(=O)OC(C)=O.CCOCC>>C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)OC(C)=O)O | O([C:2]([CH3:1])=[O:3])[C:21]([CH3:22])=[O:23].[NH2:4][c:5]1[n:6][c:7]([OH:8])[c:9]2[cH:10][c:11]([CH:12]=[CH:13][c:14]3[cH:15][cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:24][cH:25]3)[cH:26][n:27][c:28]2[n:29]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]([OH:8])[c:9]2[cH:10][c:11]([CH:12]=[CH:13][c:14]3[cH:15][cH:16][c:17... | CC(=O)OC(C)=O.Nc1nc(O)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 | CC(=O)Nc1nc(O)c2cc(C=Cc3ccc(C(=O)OC(C)=O)cc3)cnc2n1 | null | CN(C1=CC=NC=C1)C | null | Acylation | OtherReaction | bcb8ef0cf1236c78ec06babf6b4b911e85d9cf8c9484f4dea3285954ef98c514 | 25997fa7400ad5cad44073cbc165db879803e89eaa489f9f1f3a199c5d1577b6 | C(=Cc1cnc2ncncc2c1)c1ccccc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH2;D1;+0:5]):[#7;a:6]:[c:7].[O;D1;H0:8]=[C:9](-[OH;D1;+0:10])-[c:11].[C;D1;H3:12]-[C;H0;D3;+0:13](=[O;D1;H0:14])-O-[C;H0;D3;+0:15](-[C;D1;H3:16])=[O;D1;H0:17]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4](-[NH;D2;+0:5]-[C;H0;D3;+0:13](-[C;D1;H3:12])=[O;D1;H0:14]):[#7;a:6]:[c:7].[C;D1;H3:16]-[C;H0;D3;+... | 84 | [{"value": 84.0, "product": "C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)OC(C)=O)O", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | null | null | A suspension of 0.88 g of 2-amino-4-hydroxy-6-[2-(4-carboxyphenyl)ethenyl]pyrido[2,3-d]pyrimidine in 20 mL of acetic anhydride containing 0.05 g of 4-dimethylaminopyridine was heated under nitrogen at 120° C. for 3 hours. The reaction mixture was cooled to room temperature. Fifty milliliters of ether were added and the... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Carboxylic acid.Primary amine | Anhydride.Ester.Secondary amide | null | null | c1cnc2ncncc2c1.c1ccccc1 | HO- | CN(C1=CC=NC=C1)C | 120 | null | CC(=O)OC(C)=O.Nc1nc(O)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1>CN(C1=CC=NC=C1)C>CC(=O)Nc1nc(O)c2cc(C=Cc3ccc(C(=O)OC(C)=O)cc3)cnc2n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5258d9c22ca6449f97c85d5608de3d40 | CC(=O)Nc1nc(O)c2cc(C=Cc3ccc(C(=O)OC(C)=O)cc3)cnc2n1>>CC(=O)Nc1nc(O)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 | C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)OC(C)=O)O.[OH-].[Na+].C(C)(=O)O>>C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)O)O | CC(=O)[O:20][C:18]([c:17]1[cH:16][cH:15][c:14]([CH:13]=[CH:12][c:11]2[cH:10][c:9]3[c:7]([OH:8])[n:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[n:26][c:25]3[n:24][cH:23]2)[cH:22][cH:21]1)=[O:19]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]([OH:8])[c:9]2[cH:10][c:11]([CH:12]=[CH:13][c:14]3[cH:15][cH:16][c:17]([C:18](=[O:19])[OH:20... | CC(=O)Nc1nc(O)c2cc(C=Cc3ccc(C(=O)OC(C)=O)cc3)cnc2n1 | CC(=O)Nc1nc(O)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 | null | null | O | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | de9168d2ced42583c2eea21d3bcb4566a35126bc5d26b6eba6e12eb3e3ab5cec | cefbde59574146d9f3baa59e7d9a326811354c9ac350a99ea3db6f77b0d75bce | C(=Cc1cnc2ncncc2c1)c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 77 | [{"value": 77.0, "product": "C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.6, "product": "C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 0.95 g of 2-acetamido-4-hydroxy-6-[2-(4-acetoxycarbonylphenyl)ethenyl]pyrido[2,3-d]pyrimidine in 50 mL of water was added 1N aqueous sodium hydroxide until a homogenous solution was obtained. Acidification with acetic acid resulted in the formation of a yellow precipitate which was collected by filtr... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester | Carboxylic acid | null | null | c1cnc2ncncc2c1.c1ccccc1 | HO- | O | null | null | CC(=O)Nc1nc(O)c2cc(C=Cc3ccc(C(=O)OC(C)=O)cc3)cnc2n1>O>CC(=O)Nc1nc(O)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9a8146047b3a4bd2b9d6f283d20589c9 | CC(C)(C)OC(=O)CC[C@H](N)C(=O)OC(C)(C)C.Nc1nc(N)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1>>CC(C)(C)OC(=O)CC[C@H](NC(=O)c1ccc(C=Cc2cnc3nc(N)nc(N)c3c2)cc1)C(=O)OC(C)(C)C | Cl.N[C@@H](CCC(=O)OC(C)(C)C)C(=O)OC(C)(C)C.NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)O)N>>NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C=C2)N | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[CH2:8][CH2:9][C@H:10]([NH2:11])[C:34](=[O:35])[O:36][C:37]([CH3:38])([CH3:39])[CH3:40].O[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([CH:18]=[CH:19][c:20]2[cH:21][n:22][c:23]3[n:24][c:25]([NH2:26])[n:27][c:28]([NH2:29])[c:30]3[cH:31]2)[cH:32][cH:33]1>>[CH3:1][C:2]([CH3:3])... | CC(C)(C)OC(=O)CC[C@H](N)C(=O)OC(C)(C)C.Nc1nc(N)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1 | CC(C)(C)OC(=O)CC[C@H](NC(=O)c1ccc(C=Cc2cnc3nc(N)nc(N)c3c2)cc1)C(=O)OC(C)(C)C | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | C(=Cc1cnc2ncncc2c1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15]>>[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15] | null | [] | null | null | null | null | Alternatively, 2.2 g (0.0074 mol) of di-tert-butyl L-glutamate hydrochloride were allowed to react with 1.5 g (0.0049 mol) of 2,4-diamino-6-[2-(4-carboxyphenyl)ethenyl]pyrido[2,3-d]pyrimidine, to yield di-tert-butyl N-(4-[2-(2,4-diaminopyrido[2,3-d]pyrimidin-6-yl)ethenyl]benzoyl)-L-glutamate in a yield of 1.3 g (48%), ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1cnc2ncncc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)CC[C@H](N)C(=O)OC(C)(C)C.Nc1nc(N)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1>>CC(C)(C)OC(=O)CC[C@H](NC(=O)c1ccc(C=Cc2cnc3nc(N)nc(N)c3c2)cc1)C(=O)OC(C)(C)C |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-8d98757e57a247879affe4c13dc3c91d | CC(=O)Nc1nc(O)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1.CCOC(=O)CC[C@H](N)C(=O)OCC>>CCOC(=O)CC[C@H](NC(=O)c1ccc(C=Cc2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC | C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C=C2)C(=O)O)O.CN1CCOCC1.C1(=CC=CC=C1)NP(OC1=CC=CC=C1)(=O)Cl.Cl.N[C@@H](CCC(=O)OCC)C(=O)OCC>>C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C(=O)N[C@@H](CCC(=O)OCC)C(=O)OCC)C=C2)O | O[C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH:16]=[CH:17][c:18]2[cH:19][n:20][c:21]3[n:22][c:23]([NH:24][C:25]([CH3:26])=[O:27])[n:28][c:29]([OH:30])[c:31]3[cH:32]2)[cH:33][cH:34]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][C@H:8]([NH2:9])[C:35](=[O:36])[O:37][CH2:38][CH3:39]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2... | CC(=O)Nc1nc(O)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1.CCOC(=O)CC[C@H](N)C(=O)OCC | CCOC(=O)CC[C@H](NC(=O)c1ccc(C=Cc2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC | null | null | CN1C(CCC1)=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | C(=Cc1cnc2ncncc2c1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10](-[C:11])-[NH2;D1;+0:12]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10](-[C:11])-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 66 | [{"value": 66.0, "product": "C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C(=O)N[C@@H](CCC(=O)OCC)C(=O)OCC)C=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.0, "product": "C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C(=O)N[C@@H](CCC(=O)OCC)C(=O)OCC)C=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_d... | 0 | CELSIUS | 30 | MINUTE | To an ice cold solution of 1.5 g (0.0043 mol) of 2-acetamido-4-hydroxy-6-[2-(4-carboxyphenyl)ethenyl]pyrido[2,3-d]pyrimidine in 40 mL of N-methylpyrrolidone containing 1.4 mL of N-methylmorpholine was added 1.72 g (0.0064 mol) of phenyl N-phenylphosphoramidochloridate in a single portion. The resulting mixture was stir... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1cnc2ncncc2c1 | HO- | CN1C(CCC1)=O | 0 | 0.5 | CC(=O)Nc1nc(O)c2cc(C=Cc3ccc(C(=O)O)cc3)cnc2n1.CCOC(=O)CC[C@H](N)C(=O)OCC>CN1C(CCC1)=O>CCOC(=O)CC[C@H](NC(=O)c1ccc(C=Cc2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-58a4fcf706344a8895a9ceb219c4739f | CC(=O)Nc1nc(O)c2cc(C=C(C)c3ccc(C(=O)O)cc3)cnc2n1.CCOC(=O)CC[C@H](N)C(=O)OCC>>CCOC(=O)CC[C@H](NCc1ccc(C(C)=Cc2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC | N[C@@H](CCC(=O)OCC)C(=O)OCC.C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)C=C(C)C2=CC=C(C=C2)C(=O)O)O.CN1CCOCC1.C1(=CC=CC=C1)NP(OC1=CC=CC=C1)(=O)Cl>>C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)C=C(C)C2=CC=C(CN[C@@H](CCC(=O)OCC)C(=O)OCC)C=C2)O | O=[C:10](O)[c:11]1[cH:12][cH:13][c:14]([C:15]([CH3:16])=[CH:17][c:18]2[cH:19][n:20][c:21]3[n:22][c:23]([NH:24][C:25]([CH3:26])=[O:27])[n:28][c:29]([OH:30])[c:31]3[cH:32]2)[cH:33][cH:34]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][C@H:8]([NH2:9])[C:35](=[O:36])[O:37][CH2:38][CH3:39]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])... | CC(=O)Nc1nc(O)c2cc(C=C(C)c3ccc(C(=O)O)cc3)cnc2n1.CCOC(=O)CC[C@H](N)C(=O)OCC | CCOC(=O)CC[C@H](NCc1ccc(C(C)=Cc2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | OtherReaction | 07040e1642efc76553305725186fdd04f379a9459d7c4ee72b90f8f6d93eda93 | fa64142892e6dfdb381fdd81c9f6becd1fc9340df98b16c99dcdc1b0c3fb2b30 | C(=Cc1cnc2ncncc2c1)c1ccccc1 | O-[C;H0;D3;+0:1](=O)-[c:2](:[c:3]):[c:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9](-[C:10])-[NH2;D1;+0:11]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C:9](-[C:10])-[NH;D2;+0:11]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | To a solution of 0.2 g of 2-acetamido-4-hydroxy-6-[2-(4-carboxyphenyl)prop-1-enyl]pyrido[2,3-d]pyrimidine in 50 mL of N-methylpyrrolidinone containing 0.18 g of N-methylmorpholine was added 0.22 g of phenyl N-phenylphosphoramidochloridate in a single portion. After stirring the mixture at room temperature for 1 hour, 0... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amine | null | null | c1ccccc1.c1cnc2ncncc2c1 | Other | CN1C(CCC1)=O | null | 1 | CC(=O)Nc1nc(O)c2cc(C=C(C)c3ccc(C(=O)O)cc3)cnc2n1.CCOC(=O)CC[C@H](N)C(=O)OCC>CN1C(CCC1)=O>CCOC(=O)CC[C@H](NCc1ccc(C(C)=Cc2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a8a880212d33449f828faa70e18e50df | CCOC(=O)CC[C@H](NC(=O)c1ccc(C=Cc2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC>>CCOC(=O)CC[C@H](NC(=O)c1ccc(CCc2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC | C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)C=CC2=CC=C(C(=O)N[C@@H](CCC(=O)OCC)C(=O)OCC)C=C2)O.[H][H]>>C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)CCC2=CC=C(C(=O)N[C@@H](CCC(=O)OCC)C(=O)OCC)C=C2)O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][C@H:8]([NH:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH:16]=[CH:17][c:18]2[cH:19][n:20][c:21]3[n:22][c:23]([NH:24][C:25]([CH3:26])=[O:27])[n:28][c:29]([OH:30])[c:31]3[cH:32]2)[cH:33][cH:34]1)[C:35](=[O:36])[O:37][CH2:38][CH3:39]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6]... | CCOC(=O)CC[C@H](NC(=O)c1ccc(C=Cc2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC | CCOC(=O)CC[C@H](NC(=O)c1ccc(CCc2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC | null | [Pd] | FC(C(=O)O)(F)F | Reduction | Hydrogenation (double to single) | 0bc3968b35f0839c230afb4215314da278abd4e1f10e42ec3012c5512de49ea5 | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1ccc(CCc2cnc3ncncc3c2)cc1 | [#7;a:1]:[c:2]:[#7;a:3]:[c:4]:[c:5](-[CH;D2;+0:6]=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:11]>>[#7;a:1]:[c:2]:[#7;a:3]:[c:4]:[c:5](-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[c:8](:[c:9]):[c:10]):[c:11] | 56 | [{"value": 56.0, "product": "C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)CCC2=CC=C(C(=O)N[C@@H](CCC(=O)OCC)C(=O)OCC)C=C2)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of diethyl N-(4-[2-(2-acetamido-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)ethenyl]benzoyl)-L-glutamate in 30 mL of trifluoroacetic acid was hydrogenated at 55 psi of hydrogen in the presence of 1.0 g of 5% Pd/C at room temperature for 14 hours. The catalyst was removed by filtration, the filtrate evaporated under... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1cnc2ncncc2c1 | null | [Pd].FC(C(=O)O)(F)F | null | null | CCOC(=O)CC[C@H](NC(=O)c1ccc(C=Cc2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC>[Pd].FC(C(=O)O)(F)F>CCOC(=O)CC[C@H](NC(=O)c1ccc(CCc2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ceb9e204a582497382b7e2c30ba790fc | CCOC(=O)CC[C@H](NC(=O)c1ccc(C=C(C)c2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC>>CCOC(=O)CC[C@H](NC(=O)c1ccc(C(C)CC2CNc3nc(NC(C)=O)nc(O)c3C2)cc1)C(=O)OCC | C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)C(=CC2=CC=C(C(=O)N[C@@H](CCC(=O)OCC)C(=O)OCC)C=C2)C)O.[H][H].FC(C(=O)O)(F)F>>C(C)(=O)NC=1N=C(C2=C(N1)NCC(C2)CC(C)C2=CC=C(C(=O)N[C@@H](CCC(=O)OCC)C(=O)OCC)C=C2)O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][C@H:8]([NH:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][c:15]([CH:16]=[C:18]([CH3:17])[c:19]2[cH:20][n:21][c:22]3[n:23][c:24]([NH:25][C:26]([CH3:27])=[O:28])[n:29][c:30]([OH:31])[c:32]3[cH:33]2)[cH:34][cH:35]1)[C:36](=[O:37])[O:38][CH2:39][CH3:40]>>[CH3:1][CH2:2][O:3][C:4](=[O:5... | CCOC(=O)CC[C@H](NC(=O)c1ccc(C=C(C)c2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC | CCOC(=O)CC[C@H](NC(=O)c1ccc(C(C)CC2CNc3nc(NC(C)=O)nc(O)c3C2)cc1)C(=O)OCC | null | [Pd] | null | Miscellaneous | OtherReaction | a20604411b703a7ab2f08e0cc2ff033e76b54719f6ab82645d0c480fa9a7ca48 | e3fff3959aaf1f1f768c1d470ac1a5edda16cd88af5e820de158d44d48f28485 | c1ccc(CCC2CNc3ncncc3C2)cc1 | [CH3;D1;+0:1]-[C;H0;D3;+0:2](=[CH;D2;+0:3]-[c:4](:[c:5]):[c:6])-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[n;H0;D2;+0:9]:[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[c:14](-[O;D1;H1:15]):[c:16]:2:[cH;D2;+0:17]:1>>[CH3;D1;+0:1]-[CH;D3;+0:3](-[CH2;D2;+0:2]-[CH;D3;+0:7]1-[CH2;D2;+0:8]-[NH;D2;+0:9]-[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[c:14](-[O;... | null | [] | null | null | null | null | A solution of 84.4 mg of diethyl N-(4-[2-(2-acetamido-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)prop-1-enyl]benzoyl)-L-glutamate in 30 mL of trifluoroacetic acid was hydrogenated at 55 psi of hydrogen in the presence of 0.42 g of 5% Pd/C at room temperature for 24 hours. The catalyst was removed by filtration and the filtra... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1cnc2ncncc2c1 | c1ncc2c(n1)NCCC2 | c1ccccc1.c1ncc2c(n1)NCCC2 | null | [Pd] | null | null | CCOC(=O)CC[C@H](NC(=O)c1ccc(C=C(C)c2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC>[Pd]>CCOC(=O)CC[C@H](NC(=O)c1ccc(C(C)CC2CNc3nc(NC(C)=O)nc(O)c3C2)cc1)C(=O)OCC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-86d5f7c92f124300a6300776810e38b4 | CCOC(=O)CC[C@H](NC(=O)c1ccc(CCc2cnc3nc(N)nc(N)c3c2)cc1)C(=O)OCC>>Nc1nc(N)c2cc(CCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cnc2n1 | C(C)(=O)O.NC=1N=C(C2=C(N1)N=CC(=C2)CCC2=CC=C(C(=O)N[C@@H](CCC(=O)OCC)C(=O)OCC)C=C2)N.[OH-].[Na+]>>NC=1N=C(C2=C(N1)N=CC(=C2)CCC2=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O)C=C2)N | CC[O:23][C:21]([CH2:20][CH2:19][C@H:18]([NH:17][C:15]([c:14]1[cH:13][cH:12][c:11]([CH2:10][CH2:9][c:8]2[cH:7][c:6]3[c:4]([NH2:5])[n:3][c:2]([NH2:1])[n:32][c:31]3[n:30][cH:29]2)[cH:28][cH:27]1)=[O:16])[C:24](=[O:25])[O:26]CC)=[O:22]>>[NH2:1][c:2]1[n:3][c:4]([NH2:5])[c:6]2[cH:7][c:8]([CH2:9][CH2:10][c:11]3[cH:12][cH:13][... | CCOC(=O)CC[C@H](NC(=O)c1ccc(CCc2cnc3nc(N)nc(N)c3c2)cc1)C(=O)OCC | Nc1nc(N)c2cc(CCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cnc2n1 | null | null | CO | Deprotection | OtherReaction | 6e62db7aac546f574bcfb83067ba8906c30fcbfedfc37aa16b5eaad33833f45a | ed5fed81ba501ef41c88831ec6b9463b899bfdd0815c4145ae51c79addb226d0 | c1ccc(CCc2cnc3ncncc3c2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4].C-C-[O;H0;D2;+0:5]-[C:6](-[C:7])=[O;D1;H0:8]>>[C:7]-[C:6](=[O;D1;H0:8])-[OH;D1;+0:5].[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 44.5 | [{"value": 44.0, "product": "NC=1N=C(C2=C(N1)N=CC(=C2)CCC2=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O)C=C2)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.5, "product": "NC=1N=C(C2=C(N1)N=CC(=C2)CCC2=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O)C=C2)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 0.38 g of diethyl N-(4-[2-(2,4-diaminopyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl)-L-glutamate in 50 mL of methanol containing 4.6 mL of 0.5N aqueous sodium hydroxide was stirred at room temperature for 72 hours. Acetic acid (5 mL) was added, and the resulting white precipitate collected by filtration. The ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Carboxylic acid | null | null | c1cnc2ncncc2c1.c1ccccc1 | Other | CO | null | null | CCOC(=O)CC[C@H](NC(=O)c1ccc(CCc2cnc3nc(N)nc(N)c3c2)cc1)C(=O)OCC>CO>Nc1nc(N)c2cc(CCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cnc2n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-22a9633ccf2849349997022c740ada3e | CCOC(=O)CC[C@H](NC(=O)c1ccc(CCc2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC>>Nc1nc(O)c2cc(CCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cnc2n1 | C(C)(=O)O.C(C)(=O)NC=1N=C(C2=C(N1)N=CC(=C2)CCC2=CC=C(C(=O)N[C@@H](CCC(=O)OCC)C(=O)OCC)C=C2)O.[OH-].[Na+]>>NC=1N=C(C2=C(N1)N=CC(=C2)CCC2=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O)C=C2)O | CC[O:23][C:21]([CH2:20][CH2:19][C@H:18]([NH:17][C:15]([c:14]1[cH:13][cH:12][c:11]([CH2:10][CH2:9][c:8]2[cH:7][c:6]3[c:4]([OH:5])[n:3][c:2]([NH:1]C(C)=O)[n:32][c:31]3[n:30][cH:29]2)[cH:28][cH:27]1)=[O:16])[C:24](=[O:25])[O:26]CC)=[O:22]>>[NH2:1][c:2]1[n:3][c:4]([OH:5])[c:6]2[cH:7][c:8]([CH2:9][CH2:10][c:11]3[cH:12][cH:1... | CCOC(=O)CC[C@H](NC(=O)c1ccc(CCc2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC | Nc1nc(O)c2cc(CCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cnc2n1 | null | null | CO | Reduction | OtherReaction | 3470ae664dc7dafe941ba67169a508662a555b55a751b73efe889f8f008bdd31 | ad80a300d9d806bfe94f78f453e216bba67d1c1eb5e5cb0a065bbc130c4edbd1 | c1ccc(CCc2cnc3ncncc3c2)cc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]:[#7;a:5]):[#7;a:6]:[c:7].C-C-[O;H0;D2;+0:8]-[C:9](-[C:10])=[O;D1;H0:11].C-C-[O;H0;D2;+0:12]-[C:13](-[C:14])=[O;D1;H0:15]>>[#7;a:5]:[c:4]:[#7;a:3]:[c:2](-[NH2;D1;+0:1]):[#7;a:6]:[c:7].[C:14]-[C:13](=[O;D1;H0:15])-[OH;D1;+0:12].[C:10]-[C:9](=[O;D1;H0:11])-[OH;D1;+0:8] | null | [] | null | null | null | null | A homogeneous solution of 0.175 of diethyl N-(4-[2-(2-acetamido-4-hydroxypyrido[2,3-d]pyrimidin-6-yl)ethyl]benzoyl)-L-glutamate in 50 mL of methanol containing 3 mL of 1N aqueous sodium hydroxide was stirred at room temperature for 72 hours. Addition of 2 mL of acetic acid followed by centrifugation gave 0.125 g (86) o... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Secondary amide | Carboxylic acid.Carboxylic acid.Primary amine | null | null | c1cnc2ncncc2c1.c1ccccc1 | HO- | CO | null | null | CCOC(=O)CC[C@H](NC(=O)c1ccc(CCc2cnc3nc(NC(C)=O)nc(O)c3c2)cc1)C(=O)OCC>CO>Nc1nc(O)c2cc(CCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)cnc2n1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5235adf5a47c4d5ea3963a1686188611 | CCOC(=O)CC[C@H](NC(=O)c1ccc(C(C)CC2CNc3nc(NC(C)=O)nc(O)c3C2)cc1)C(=O)OCC>>CC(CC1CNc2nc(N)nc(O)c2C1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 | C(C)(=O)NC=1N=C(C2=C(N1)NCC(C2)CC(C)C2=CC=C(C(=O)N[C@@H](CCC(=O)OCC)C(=O)OCC)C=C2)O>>NC=1N=C(C2=C(N1)NCC(C2)CC(C)C2=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O)C=C2)O | CC[O:28][C:26]([CH2:25][CH2:24][C@H:23]([NH:22][C:20]([c:19]1[cH:18][cH:17][c:16]([CH:2]([CH3:1])[CH2:3][CH:4]2[CH2:5][NH:6][c:7]3[n:8][c:9]([NH:10]C(C)=O)[n:11][c:12]([OH:13])[c:14]3[CH2:15]2)[cH:33][cH:32]1)=[O:21])[C:29](=[O:30])[O:31]CC)=[O:27]>>[CH3:1][CH:2]([CH2:3][CH:4]1[CH2:5][NH:6][c:7]2[n:8][c:9]([NH2:10])[n:... | CCOC(=O)CC[C@H](NC(=O)c1ccc(C(C)CC2CNc3nc(NC(C)=O)nc(O)c3C2)cc1)C(=O)OCC | CC(CC1CNc2nc(N)nc(O)c2C1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 | null | null | [OH-].[Na+] | Reduction | OtherReaction | 3470ae664dc7dafe941ba67169a508662a555b55a751b73efe889f8f008bdd31 | ad80a300d9d806bfe94f78f453e216bba67d1c1eb5e5cb0a065bbc130c4edbd1 | c1ccc(CCC2CNc3ncncc3C2)cc1 | C-C(=O)-[NH;D2;+0:1]-[c:2](:[#7;a:3]:[c:4]):[#7;a:5]:[c:6]-[#7:7].C-C-[O;H0;D2;+0:8]-[C:9](-[C:10])=[O;D1;H0:11].C-C-[O;H0;D2;+0:12]-[C:13](-[C:14])=[O;D1;H0:15]>>[#7:7]-[c:6]:[#7;a:5]:[c:2](-[NH2;D1;+0:1]):[#7;a:3]:[c:4].[C:14]-[C:13](=[O;D1;H0:15])-[OH;D1;+0:12].[C:10]-[C:9](=[O;D1;H0:11])-[OH;D1;+0:8] | 67.3 | [{"value": 67.0, "product": "NC=1N=C(C2=C(N1)NCC(C2)CC(C)C2=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O)C=C2)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.3, "product": "NC=1N=C(C2=C(N1)NCC(C2)CC(C)C2=CC=C(C(=O)N[C@@H](CCC(=O)O)C(=O)O)C=C2)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | A homogeneous solution of 17.5 mg of diethyl N-(4-[1-(2-acetamido-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)prop-2-yl]benzoyl)-L-glutamate in 2 mL of methanolic sodium hydroxide solution was allowed to stand at room temperature for 72 hours. Most of the solvent was then removed under reduced pressure and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Secondary amide | Carboxylic acid.Carboxylic acid.Primary amine | null | null | c1ncc2c(n1)NCCC2.c1ccccc1 | HO- | [OH-].[Na+] | null | 72 | CCOC(=O)CC[C@H](NC(=O)c1ccc(C(C)CC2CNc3nc(NC(C)=O)nc(O)c3C2)cc1)C(=O)OCC>[OH-].[Na+]>CC(CC1CNc2nc(N)nc(O)c2C1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a9955ff316c64595b85c3b8257f1612d | CCNCC.COc1ccc(-c2cc(C(=O)O)c3ccccc3n2)cc1>>CCN(CC)C(=O)c1cc(-c2ccc(OC)cc2)nc2ccccc12 | COC1=CC=C(C=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)O.S(=O)(Cl)Cl.C(C)NCC>>C(C)N(C(=O)C1=CC(=NC2=CC=CC=C12)C1=CC=C(C=C1)OC)CC | [CH3:1][CH2:2][NH:3][CH2:4][CH3:5].O[C:6](=[O:7])[c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]2)[n:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]12>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([O:15][CH3:16])[cH:17][cH:18]2)[n:19][c:20]2[... | CCNCC.COc1ccc(-c2cc(C(=O)O)c3ccccc3n2)cc1 | CCN(CC)C(=O)c1cc(-c2ccc(OC)cc2)nc2ccccc12 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccc(-c2ccc3ccccc3n2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C;D1;H3:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C;D1;H3:13]>>[C;D1;H3:9]-[C:10]-[N;H0;D3;+0:11](-[C:12]-[C;D1;H3:13])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | null | null | null | null | The procedure of Example 3 is followed using 2-(4-methoxyphenyl)-quinoline-4-carboxylic acid (5 g), thionyl chloride (15 ml) and diethylamine (18.4 ml) as the starting materials.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2ncccc2c1 | HO- | null | null | null | CCNCC.COc1ccc(-c2cc(C(=O)O)c3ccccc3n2)cc1>>CCN(CC)C(=O)c1cc(-c2ccc(OC)cc2)nc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-620b6e9defaf429f96f6b5bd0103afc4 | CCC(C)NC.O=C(O)c1cc(-c2ccccc2Cl)nc2ccccc12>>CCC(C)N(C)C(=O)c1cc(-c2ccccc2Cl)nc2ccccc12 | ClC1=C(C=CC=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)O.S(=O)(Cl)Cl.CNC(C)CC>>CN(C(=O)C1=CC(=NC2=CC=CC=C12)C1=C(C=CC=C1)Cl)C(CC)C | [CH3:1][CH2:2][CH:3]([CH3:4])[NH:5][CH3:6].O[C:7](=[O:8])[c:9]1[cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl:18])[n:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]12>>[CH3:1][CH2:2][CH:3]([CH3:4])[N:5]([CH3:6])[C:7](=[O:8])[c:9]1[cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]2[Cl:18])[n:19][c:20]2[... | CCC(C)NC.O=C(O)c1cc(-c2ccccc2Cl)nc2ccccc12 | CCC(C)N(C)C(=O)c1cc(-c2ccccc2Cl)nc2ccccc12 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccc(-c2ccc3ccccc3n2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10](-[C;D1;H3:11])-[NH;D2;+0:12]-[C;D1;H3:13]>>[C:9]-[C:10](-[C;D1;H3:11])-[N;H0;D3;+0:12](-[C;D1;H3:13])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | null | null | null | null | The procedure of Example 3 is followed using 2-(2-chlorophenyl)-quinoline-4-carboxylic acid (5.7 g), thionyl chloride (15 ml) and N-methylbut-2-ylamine (15 ml) as the starting materials.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2ncccc2c1 | HO- | null | null | null | CCC(C)NC.O=C(O)c1cc(-c2ccccc2Cl)nc2ccccc12>>CCC(C)N(C)C(=O)c1cc(-c2ccccc2Cl)nc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1bb9202aa76b42f5beaa7619357f4f18 | CCNC(C)CC.O=C(O)c1cc(-c2ccccc2Cl)nc2ccccc12>>CCC(C)N(CC)C(=O)c1cc(-c2ccccc2Cl)nc2ccccc12 | ClC1=C(C=CC=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)O.C(C)NC(C)CC>>C(C)N(C(=O)C1=CC(=NC2=CC=CC=C12)C1=C(C=CC=C1)Cl)C(CC)C | [CH3:1][CH2:2][CH:3]([CH3:4])[NH:5][CH2:6][CH3:7].O[C:8](=[O:9])[c:10]1[cH:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[Cl:19])[n:20][c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]12>>[CH3:1][CH2:2][CH:3]([CH3:4])[N:5]([CH2:6][CH3:7])[C:8](=[O:9])[c:10]1[cH:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[Cl:19... | CCNC(C)CC.O=C(O)c1cc(-c2ccccc2Cl)nc2ccccc12 | CCC(C)N(CC)C(=O)c1cc(-c2ccccc2Cl)nc2ccccc12 | null | null | S(=O)(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccc(-c2ccc3ccccc3n2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10](-[C;D1;H3:11])-[NH;D2;+0:12]-[C:13]-[C;D1;H3:14]>>[C:9]-[C:10](-[C;D1;H3:11])-[N;H0;D3;+0:12](-[C:13]-[C;D1;H3:14])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | null | null | null | null | The procedure of Example 3 is followed using 2-(2-chlorophenyl)-quinoline-4-carboxylic acid (2.8 g), thionyl chloride (10 ml) and N-ethylbut-2-ylamine (4 g) as the starting materials.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2ncccc2c1 | HO- | S(=O)(Cl)Cl | null | null | CCNC(C)CC.O=C(O)c1cc(-c2ccccc2Cl)nc2ccccc12>S(=O)(Cl)Cl>CCC(C)N(CC)C(=O)c1cc(-c2ccccc2Cl)nc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ca34bcb87e9e457fb9f9bea9ba147c0f | CCC(C)NC.O=C(O)c1cc(-c2ccccc2)cc2ccccc12>>CCC(C)N(C)C(=O)c1cc(-c2ccccc2)cc2ccccc12 | C1(=CC=CC=C1)C=1C=C(C2=CC=CC=C2C1)C(=O)O.S(=O)(Cl)Cl.CNC(C)CC>>CN(C(=O)C1=CC(=CC2=CC=CC=C12)C1=CC=CC=C1)C(CC)C | [CH3:1][CH2:2][CH:3]([CH3:4])[NH:5][CH3:6].O[C:7](=[O:8])[c:9]1[cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12>>[CH3:1][CH2:2][CH:3]([CH3:4])[N:5]([CH3:6])[C:7](=[O:8])[c:9]1[cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][c:19]2[cH:20][cH:... | CCC(C)NC.O=C(O)c1cc(-c2ccccc2)cc2ccccc12 | CCC(C)N(C)C(=O)c1cc(-c2ccccc2)cc2ccccc12 | null | null | N1=CC=CC=C1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccc(-c2ccc3ccccc3c2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[C;D1;H3:8])-[NH;D2;+0:9]-[C;D1;H3:10]>>[C:6]-[C:7](-[C;D1;H3:8])-[N;H0;D3;+0:9](-[C;D1;H3:10])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | The procedure of Example 20 is followed using 3-phenylnaphthalene-1-carboxylic acid (4.3 g), thionyl chloride (20 ml) and N-methylbut-2-ylamine (1.5 g) in pyridine (20 ml) as the starting materials. After recrystallisation from petroleum ether, N-methyl-N-(1-methylpropyl)-3-phenylnaphthalene-1-carboxamide (2.8 g), melt... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2ccccc2c1 | HO- | N1=CC=CC=C1 | null | null | CCC(C)NC.O=C(O)c1cc(-c2ccccc2)cc2ccccc12>N1=CC=CC=C1>CCC(C)N(C)C(=O)c1cc(-c2ccccc2)cc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-56751636a7e448c280ff407127a64848 | CCNCC.CCOC(=O)c1cc(-c2ccc(C)cc2)nc2ccccc12>>CCN(CC)C(=O)c1cc(-c2ccc(C)cc2)nc2ccccc12 | CC1=CC=C(C=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)OCC.C(CCC)[Li].C(C)NCC.C(C)(=O)O>>C(C)N(C(=O)C1=CC(=NC2=CC=CC=C12)C1=CC=C(C=C1)C)CC | [CH3:1][CH2:2][NH:3][CH2:4][CH3:5].CCO[C:6](=[O:7])[c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([CH3:15])[cH:16][cH:17]2)[n:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]([CH3:15])[cH:16][cH:17]2)[n:18][c:19]2[cH:20][cH:... | CCNCC.CCOC(=O)c1cc(-c2ccc(C)cc2)nc2ccccc12 | CCN(CC)C(=O)c1cc(-c2ccc(C)cc2)nc2ccccc12 | null | null | O1CCCC1.CCCCCC.O | Acylation | Aminolysis of esters | d147787750807073759132276086de98566af6772417f9288b6300bf1de7801c | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | c1ccc(-c2ccc3ccccc3n2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C;D1;H3:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C;D1;H3:13]>>[C;D1;H3:9]-[C:10]-[N;H0;D3;+0:11](-[C:12]-[C;D1;H3:13])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | 0 | CELSIUS | 15 | MINUTE | A 1.6M solution of butyllithium in hexane (22.5 ml) is added, at ambient temperature and under a nitrogen atmosphere, to diethylamine (5.5 ml) in anhydrous tetrahydrofuran (50 ml). After stirring for 15 minutes, the mixture is cooled to 0° C. and ethyl 2-(4-methylphenyl)-quinoline-4-carboxylate (5.25 g) is then introdu... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2ncccc2c1 | HO- | O1CCCC1.CCCCCC.O | 0 | 0.25 | CCNCC.CCOC(=O)c1cc(-c2ccc(C)cc2)nc2ccccc12>O1CCCC1.CCCCCC.O>CCN(CC)C(=O)c1cc(-c2ccc(C)cc2)nc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-605d2e53e6d9416f9d21db9d3466c654 | C1CCNC1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12>>O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCC1 | C(CCC)[Li].C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)OCC.N1CCCC1>>C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)N1CCCC1 | [NH:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1.CCO[C:2](=[O:1])[c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[O:1]=[C:2]([c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12)[N:19]1[CH2:20][CH2:21][CH2:22][C... | C1CCNC1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12 | O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCC1 | null | null | O1CCCC1.CCCCCC | Acylation | Aminolysis of esters | cc20831350961a38b27e2ed601d884ffe57c6a4a78a00094843b6a67d4a3333c | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:13]1-[C:9]-[C:10]-[C:11]-[C:12]-1)-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | null | null | null | null | The procedure of Example 24 is followed using ethyl 2-phenylquinazoline-4-carboxylate (3 g), pyrrolidine (3 ml), a 1.6M solution of butyllithium in hexane (15 ml) and tetrahydrofuran (25 ml) as the starting materials. After recrystallisation from ethanol, 1-[(2-phenylquinazolin-4-yl)-carbonyl]-pyrrolidine (2.1 g), melt... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.c1ccc2ncncc2c1.C1CC[NH]C1 | HO- | O1CCCC1.CCCCCC | null | null | C1CCNC1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12>O1CCCC1.CCCCCC>O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c8e86f5aa39347f99353395436cf5781 | C1CCNCC1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12>>O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCCC1 | C(CCC)[Li].C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)OCC.N1CCCCC1>>C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)N1CCCCC1 | [NH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1.CCO[C:2](=[O:1])[c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[O:1]=[C:2]([c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12)[N:19]1[CH2:20][CH2:21][C... | C1CCNCC1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12 | O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCCC1 | null | null | O1CCCC1.CCCCCC | Acylation | Aminolysis of esters | ce8275f1d7811593d008aaa00f9bfc7989dfa4c2d2aff51886f6f1df30984cf4 | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCCC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:9]-[C:10]-[N;H0;D3;+0:11](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1)-[C:12]-[C:13] | null | [] | null | null | null | null | The procedure of Example 24 is followed using ethyl 2-phenylquinazoline-4-carboxylate (3.3 g), piperidine, (2.5 ml), a 1.6M solution of butyllithium in hexane (15 ml) and tetrahydrofuran (20 ml) as the starting materials. After recrystallisation from ethanol, 1-[(2-phenylquinazolin-4-yl)-carbonyl]-piperidine (2.6 g), m... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HO- | O1CCCC1.CCCCCC | null | null | C1CCNCC1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12>O1CCCC1.CCCCCC>O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e6078071e7154cc1aeb2730cc80a7dd2 | C1COCCN1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12>>O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCOCC1 | C(CCC)[Li].C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)OCC.N1CCOCC1>>C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)N1CCOCC1 | [NH:19]1[CH2:20][CH2:21][O:22][CH2:23][CH2:24]1.CCO[C:2](=[O:1])[c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[O:1]=[C:2]([c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12)[N:19]1[CH2:20][CH2:21][O:2... | C1COCCN1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12 | O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCOCC1 | null | null | O1CCCC1.CCCCCC | Acylation | Aminolysis of esters | a16c74d831fa28fe1a25b1b8d1072fd9b49d7ad2466695bd2dbbf862cf79e686 | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCOCC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[#8:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:12]1-[C:11]-[C:10]-[#8:9]-[C:14]-[C:13]-1)-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | null | null | null | null | The procedure of Example 24 is followed using ethyl 2-phenylquinazoline-4-carboxylate (3.1 g), morpholine (2 ml), a 1.6M solution of butyllithium in hexane (15 ml) and tetrahydrofuran (20 ml) as the starting materials. After recrystallisation from ethanol, 4-[(2-phenylquinazolin-4-yl)-carbonyl]-morpholine (3 g), meltin... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.c1ccc2ncncc2c1.C1COCC[NH]1 | HO- | O1CCCC1.CCCCCC | null | null | C1COCCN1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12>O1CCCC1.CCCCCC>O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCOCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e8d194393b0c416a8aa403ad9f2e7177 | CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12.OC1CCNCC1>>O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCC(O)CC1 | C(CCC)[Li].C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)OCC.N1CCC(CC1)O>>C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)N1CCC(CC1)O | CCO[C:2](=[O:1])[c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12.[NH:19]1[CH2:20][CH2:21][CH:22]([OH:23])[CH2:24][CH2:25]1>>[O:1]=[C:2]([c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12)[N:19]1[CH2:20][C... | CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12.OC1CCNCC1 | O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCC(O)CC1 | null | null | O1CCCC1.CCCCCC | Acylation | Aminolysis of esters | ce8275f1d7811593d008aaa00f9bfc7989dfa4c2d2aff51886f6f1df30984cf4 | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCCC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:9]-[C:10]-[N;H0;D3;+0:11](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1)-[C:12]-[C:13] | null | [] | null | null | null | null | The procedure of Example 24 is followed using ethyl 2-phenylquinazoline-4-carboxylate (2 g), piperidin-4-ol (1.4 g), a 1.6M solution of butyllithium in hexane (18 ml) and tetrahydrofuran (30 ml) as the starting materials. After recrystallisation from a mixture of methanol and methylene chloride, 1-[(2-phenylquinazolin-... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HO- | O1CCCC1.CCCCCC | null | null | CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12.OC1CCNCC1>O1CCCC1.CCCCCC>O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCC(O)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7c88b728e58b4a6184b96d57465d7b30 | C1CCCNCC1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12>>O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCCCC1 | C(CCC)[Li].C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)OCC.N1CCCCCC1>>C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)N1CCCCCC1 | [NH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1.CCO[C:2](=[O:1])[c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12>>[O:1]=[C:2]([c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12)[N:19]1[CH2:20][C... | C1CCCNCC1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12 | O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCCCC1 | null | null | O1CCCC1.CCCCCC | Acylation | Aminolysis of esters | fd5b185137c68d178cd7e727e64092d7ecde9df29ac6752e9af69a3e78991ce2 | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCCCC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:9]-[C:10]-[N;H0;D3;+0:11](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1)-[C:12]-[C:13] | null | [] | null | null | null | null | The procedure of Example 24 is followed using ethyl 2-phenylquinazoline-4-carboxylate (3 g), 2,3,4,5,6,7-hexahydroazepine (2.8 ml), a 1.6M solution of butyllithium in hexane (15 ml) and tetrahydrofuran (20 ml) as the starting materials. After recrystallisation from ethanol, 2,3,4,5,6,7-hexahydro-1-[(2-phenylquinazolin-... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | C1CCCNCC1 | C1CCC[NH]CC1 | c1ccccc1.c1ccc2ncncc2c1.C1CCC[NH]CC1 | HO- | O1CCCC1.CCCCCC | null | null | C1CCCNCC1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12>O1CCCC1.CCCCCC>O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-e76cd4fbb64d452abec59efb31cdd895 | CC1CCCNC1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12>>CC1CCCN(C(=O)c2nc(-c3ccccc3)nc3ccccc23)C1 | C(CCC)[Li].C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)OCC.CC1CNCCC1>>CC1CN(CCC1)C(=O)C1=NC(=NC2=CC=CC=C12)C1=CC=CC=C1 | [CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][NH:6][CH2:25]1.CCO[C:7](=[O:8])[c:9]1[n:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][N:6]([C:7](=[O:8])[c:9]2[n:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[n:18][c:19]3[cH:20]... | CC1CCCNC1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12 | CC1CCCN(C(=O)c2nc(-c3ccccc3)nc3ccccc23)C1 | null | null | O1CCCC1.CCCCCC | Acylation | Aminolysis of esters | ce8275f1d7811593d008aaa00f9bfc7989dfa4c2d2aff51886f6f1df30984cf4 | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCCC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:9]-[C:10]-[N;H0;D3;+0:11](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1)-[C:12]-[C:13] | null | [] | null | null | null | null | The procedure of Example 24 is followed using ethyl 2-phenylquinazoline-4-carboxylate (3 g), 3-methylpiperidine (3 ml), a 1.6M solution of butyllithium in hexane (15 ml) and tetrahydrofuran (20 ml) as the starting materials. After recrystallisation from isopropyl ether, 3-methyl-1-[(2-phenylquinazolin-4-yl)-carbonyl]-p... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccc2ncncc2c1 | HO- | O1CCCC1.CCCCCC | null | null | CC1CCCNC1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12>O1CCCC1.CCCCCC>CC1CCCN(C(=O)c2nc(-c3ccccc3)nc3ccccc23)C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c1dcd63c5c9042e1aa630b0cfe35ca4a | CC1CCCCN1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12>>CC1CCCCN1C(=O)c1nc(-c2ccccc2)nc2ccccc12 | C(CCC)[Li].C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)OCC.CC1NCCCC1>>CC1N(CCCC1)C(=O)C1=NC(=NC2=CC=CC=C12)C1=CC=CC=C1 | [CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]1.CCO[C:8](=[O:9])[c:10]1[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[n:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]12>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:8](=[O:9])[c:10]1[n:11][c:12](-[c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[n:19][c:20]... | CC1CCCCN1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12 | CC1CCCCN1C(=O)c1nc(-c2ccccc2)nc2ccccc12 | null | null | O1CCCC1.CCCCCC | Acylation | Aminolysis of esters | ce8275f1d7811593d008aaa00f9bfc7989dfa4c2d2aff51886f6f1df30984cf4 | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCCC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10](-[C;D1;H3:11])-[NH;D2;+0:12]-[C:13]-[C:14]>>[C:9]-[C:10](-[C;D1;H3:11])-[N;H0;D3;+0:12](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1)-[C:13]-[C:14] | null | [] | null | null | null | null | The procedure of Example 24 is followed using ethyl 2-phenylquinazoline-4-carboxylate (3 g), 2-methylpiperidine (3 ml), a 1.6M solution of butyllithium in hexane (15 ml) and tetrahydrofuran (20 ml) as the starting materials. After recrystallisation from ethanol, 2-methyl-1-[(2-phenylquinazolin-4yl)-carbonyl]-piperidine... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccc2ncncc2c1 | HO- | O1CCCC1.CCCCCC | null | null | CC1CCCCN1.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12>O1CCCC1.CCCCCC>CC1CCCCN1C(=O)c1nc(-c2ccccc2)nc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-f69f351aa658478dad15a30b3cbda546 | CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12.OCC1CCCNC1>>O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCC(CO)C1 | C(CCC)[Li].C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)OCC.N1CC(CCC1)CO>>C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)N1CC(CCC1)CO | CCO[C:2](=[O:1])[c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12.[NH:19]1[CH2:20][CH2:21][CH2:22][CH:23]([CH2:24][OH:25])[CH2:26]1>>[O:1]=[C:2]([c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12)[N:19]1[C... | CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12.OCC1CCCNC1 | O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCC(CO)C1 | null | null | O1CCCC1.CCCCCC | Acylation | Aminolysis of esters | ce8275f1d7811593d008aaa00f9bfc7989dfa4c2d2aff51886f6f1df30984cf4 | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCCC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:9]-[C:10]-[N;H0;D3;+0:11](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1)-[C:12]-[C:13] | null | [] | null | null | null | null | The procedure of Example 24 is followed using ethyl 2-phenylquinazoline-4-carboxylate (3 g), piperidine-3-methanol (2.9 g), a 1.6M solution of butyllithium in hexane (31 ml) and tetrahydrofuran (20 ml) as the starting materials. After recrystallisation from ethyl acetate, 1-[(2-phenylquinazolin-4-yl)-carbonyl]-piperidi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HO- | O1CCCC1.CCCCCC | null | null | CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12.OCC1CCCNC1>O1CCCC1.CCCCCC>O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCC(CO)C1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-4819cb8d9f104efaad3295b34f3731f5 | CC1CCCC(C)N1.O=C(O)c1cc(-c2ccccc2Cl)nc2ccccc12>>CC1CCCC(C)N1C(=O)c1cc(-c2ccccc2Cl)nc2ccccc12 | ClC1=C(C=CC=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)O.S(=O)(Cl)Cl.CC1NC(CCC1)C>>ClC1=C(C=CC=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)N1C(CCCC1C)C | [CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH:6]([CH3:7])[NH:8]1.O[C:9](=[O:10])[c:11]1[cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]2[Cl:20])[n:21][c:22]2[cH:23][cH:24][cH:25][cH:26][c:27]12>>[CH3:1][CH:2]1[CH2:3][CH2:4][CH2:5][CH:6]([CH3:7])[N:8]1[C:9](=[O:10])[c:11]1[cH:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][cH:... | CC1CCCC(C)N1.O=C(O)c1cc(-c2ccccc2Cl)nc2ccccc12 | CC1CCCC(C)N1C(=O)c1cc(-c2ccccc2Cl)nc2ccccc12 | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1cc(-c2ccccc2)nc2ccccc12)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10](-[C;D1;H3:11])-[NH;D2;+0:12]-[C:13](-[C;D1;H3:14])-[C:15]>>[C:9]-[C:10](-[C;D1;H3:11])-[N;H0;D3;+0:12](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1)-[C:13](-[C;D1;H3:14])-[C:15] | null | [] | null | null | null | null | 2-(2-Chlorophenyl)-quinoline-4-carboxylic acid (5.7 g) and thionyl chloride (15 ml) are heated under reflux for 1 hour. The thionyl chloride is evaporated off, the residue is taken up in toluene (40 ml) and the toluene is also evaporated off. Toluene (50 ml) is then added to the residue obtained, followed by the dropwi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccc2ncccc2c1 | HO- | null | null | null | CC1CCCC(C)N1.O=C(O)c1cc(-c2ccccc2Cl)nc2ccccc12>>CC1CCCC(C)N1C(=O)c1cc(-c2ccccc2Cl)nc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-542fb92314014406b06cfa5a8bea3254 | CNc1ccccc1.O=C(Cl)c1cc(-c2ccccc2)nc2ccccc12>>CN(C(=O)c1cc(-c2ccccc2)nc2ccccc12)c1ccccc1 | Cl.C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)Cl.CNC1=CC=CC=C1>>CN(C(=O)C1=CC(=NC2=CC=CC=C12)C1=CC=CC=C1)C1=CC=CC=C1 | [CH3:1][NH:2][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1.Cl[C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12>>[CH3:1][N:2]([C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12... | CNc1ccccc1.O=C(Cl)c1cc(-c2ccccc2)nc2ccccc12 | CN(C(=O)c1cc(-c2ccccc2)nc2ccccc12)c1ccccc1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Nc1ccccc1)c1cc(-c2ccccc2)nc2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C;D1;H3:9]-[NH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:9]-[N;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1)-[c:11](:[c:12]):[c:13] | null | [] | 0 | CELSIUS | 30 | MINUTE | 2-Phenylquinoline-4-carboxylic acid chloride hydrochloride (10.7 g) is added in portions over a period of 15 minutes, with stirring, to a solution of N-methylaniline (12.8 g) in methylene chloride (75 ml), cooled to 0° C. The mixture is stirred for 2 hours 30 minutes at 10° C. The solution obtained is washed with a 20%... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2ncccc2c1.c1ccccc1 | HCl | C(Cl)Cl | 0 | 0.5 | CNc1ccccc1.O=C(Cl)c1cc(-c2ccccc2)nc2ccccc12>C(Cl)Cl>CN(C(=O)c1cc(-c2ccccc2)nc2ccccc12)c1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-5179e043814e4524a8dd529115ef50e0 | CNC.O=C(Cl)c1cc(-c2ccccc2)nc2ccccc12>>CN(C)C(=O)c1cc(-c2ccccc2)nc2ccccc12 | Cl.C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)Cl.CNC>>CN(C(=O)C1=CC(=NC2=CC=CC=C12)C1=CC=CC=C1)C | [CH3:1][NH:2][CH3:3].Cl[C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[n:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12>>[CH3:1][N:2]([CH3:3])[C:4](=[O:5])[c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[n:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12 | CNC.O=C(Cl)c1cc(-c2ccccc2)nc2ccccc12 | CN(C)C(=O)c1cc(-c2ccccc2)nc2ccccc12 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(-c2ccc3ccccc3n2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C;D1;H3:9]-[NH;D2;+0:10]-[C;D1;H3:11]>>[C;D1;H3:9]-[N;H0;D3;+0:10](-[C;D1;H3:11])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | 0 | CELSIUS | 1 | HOUR | 2-Phenylquinoline-4-carboxylic acid chloride hydrochloride (10.7 g) is added in portions over a period of 1 hour to a stirred solution of N,N-dimethylamine (18.9 g) in methylene chloride (100 ml), cooled to 0° C. The mixture is stirred for 1 hour at 0° C. The solution is evaporated under reduced pressure. The residue i... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2ncccc2c1 | HCl | C(Cl)Cl | 0 | 1 | CNC.O=C(Cl)c1cc(-c2ccccc2)nc2ccccc12>C(Cl)Cl>CN(C)C(=O)c1cc(-c2ccccc2)nc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-a8d870d60c46421f8f40204640049401 | CCC(C)NC.O=C(Cl)c1cc(-c2ccccc2)nc2ccccc12>>CCC(C)N(C)C(=O)c1cc(-c2ccccc2)nc2ccccc12 | Cl.C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)Cl.CNC(C)CC>>CN(C(=O)C1=CC(=NC2=CC=CC=C12)C1=CC=CC=C1)C(CC)C | [CH3:1][CH2:2][CH:3]([CH3:4])[NH:5][CH3:6].Cl[C:7](=[O:8])[c:9]1[cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18][c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]12>>[CH3:1][CH2:2][CH:3]([CH3:4])[N:5]([CH3:6])[C:7](=[O:8])[c:9]1[cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[n:18][c:19]2[cH:20][cH:2... | CCC(C)NC.O=C(Cl)c1cc(-c2ccccc2)nc2ccccc12 | CCC(C)N(C)C(=O)c1cc(-c2ccccc2)nc2ccccc12 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | c1ccc(-c2ccc3ccccc3n2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10](-[C;D1;H3:11])-[NH;D2;+0:12]-[C;D1;H3:13]>>[C:9]-[C:10](-[C;D1;H3:11])-[N;H0;D3;+0:12](-[C;D1;H3:13])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | null | null | null | null | The procedure of Example 42 is followed using 2-phenylquinoline-4-carboxylic acid chloride hydrochloride (10.7 g) and N-methylbut-2-ylamine (10.5 g) in methylene chloride (75 ml) as the starting materials.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2ncccc2c1 | HCl | C(Cl)Cl | null | null | CCC(C)NC.O=C(Cl)c1cc(-c2ccccc2)nc2ccccc12>C(Cl)Cl>CCC(C)N(C)C(=O)c1cc(-c2ccccc2)nc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-0de83e3c0a11451fae3ce535e9b44bab | CNC1CCCCC1.O=C(Cl)c1cc(-c2ccccc2)nc2ccccc12>>CN(C(=O)c1cc(-c2ccccc2)nc2ccccc12)C1CCCCC1 | Cl.C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=C1)C(=O)Cl.CNC1CCCCC1>>C1(CCCCC1)N(C(=O)C1=CC(=NC2=CC=CC=C12)C1=CC=CC=C1)C | [CH3:1][NH:2][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1.Cl[C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12>>[CH3:1][N:2]([C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c... | CNC1CCCCC1.O=C(Cl)c1cc(-c2ccccc2)nc2ccccc12 | CN(C(=O)c1cc(-c2ccccc2)nc2ccccc12)C1CCCCC1 | null | null | C(Cl)Cl | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(NC1CCCCC1)c1cc(-c2ccccc2)nc2ccccc12 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10](-[NH;D2;+0:11]-[C;D1;H3:12])-[C:13]>>[C:9]-[C:10](-[N;H0;D3;+0:11](-[C;D1;H3:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1)-[C:13] | null | [] | null | null | null | null | The procedure of Example 41 is followed using 2-phenylquinoline-4-carboxylic acid chloride hydrochloride (9.1 g) and N-methylcyclohexylamine (13.5 g) in methylene chloride (100 ml) as the starting materials.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccc2ncccc2c1.C1CCCCC1 | HCl | C(Cl)Cl | null | null | CNC1CCCCC1.O=C(Cl)c1cc(-c2ccccc2)nc2ccccc12>C(Cl)Cl>CN(C(=O)c1cc(-c2ccccc2)nc2ccccc12)C1CCCCC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-043d97be20af4fc09d3bc3b55d5c985c | CCN(CC1CCN(Cc2ccccc2)CC1)C(=O)c1cc(-c2ccccc2)nc2ccccc12>>CCN(CC1CCNCC1)C(=O)c1cc(-c2ccccc2)nc2ccccc12 | C(C)(=O)[O-].[Na+].C(C)N(C(=O)C1=CC(=NC2=CC=CC=C12)C1=CC=CC=C1)CC1CCN(CC1)CC1=CC=CC=C1>>C(C)N(C(=O)C1=CC(=NC2=CC=CC=C12)C1=CC=CC=C1)CC1CCNCC1 | c1ccc(C[N:8]2[CH2:7][CH2:6][CH:5]([CH2:4][N:3]([CH2:2][CH3:1])[C:11](=[O:12])[c:13]3[cH:14][c:15](-[c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21]4)[n:22][c:23]4[cH:24][cH:25][cH:26][cH:27][c:28]34)[CH2:10][CH2:9]2)cc1>>[CH3:1][CH2:2][N:3]([CH2:4][CH:5]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1)[C:11](=[O:12])[c:13]1[cH:14][c:15... | CCN(CC1CCN(Cc2ccccc2)CC1)C(=O)c1cc(-c2ccccc2)nc2ccccc12 | CCN(CC1CCNCC1)C(=O)c1cc(-c2ccccc2)nc2ccccc12 | null | Cl.[Pd] | C(C)O | Deprotection | Hydrogenolysis of tertiary amines | cd3c1aa319cad45f383f17cc0b8bfc8337d7078d779f654933f9a447e64292a5 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | O=C(NCC1CCNCC1)c1cc(-c2ccccc2)nc2ccccc12 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | 64.7 | [{"value": 64.7, "product": "C(C)N(C(=O)C1=CC(=NC2=CC=CC=C12)C1=CC=CC=C1)CC1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | N-Ethyl-N-[(1-benzylpiperidin-4-yl)-methyl]-2-phenylquinoline-4-carboxamide (9.6 g) is heated in ethanol (200 ml) until it has dissolved. After cooling, this solution is treated with a 4.5N ethanolic solution of hydrogen chloride (9.2 ml), 10% strength palladium-on-charcoal (2.9 g) as a catalyst and, finally, sodium ac... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccccc1.c1ccc2ncccc2c1 | Other | Cl.[Pd].C(C)O | null | 5 | CCN(CC1CCN(Cc2ccccc2)CC1)C(=O)c1cc(-c2ccccc2)nc2ccccc12>Cl.[Pd].C(C)O>CCN(CC1CCNCC1)C(=O)c1cc(-c2ccccc2)nc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-772e8adb0ac14f1c9eda2ffcd2994bb9 | CCN(CCCC1CCN(Cc2ccccc2)CC1)C(=O)c1cc(-c2ccccc2)nc2ccccc12.CCO.O=C(Cl)OCC(Cl)(Cl)Cl>>CCN(CCCC1CCNCC1)C(=O)c1cc(-c2ccccc2)nc2ccccc12.CCNCC.Cc1ccccc1 | C(C)O.C(C)N(C(=O)C1=CC(=NC2=CC=CC=C12)C1=CC=CC=C1)CCCC1CCN(CC1)CC1=CC=CC=C1.[OH-].[K+].ClC(=O)OCC(Cl)(Cl)Cl>>C1(=CC=CC=C1)C.C(C)NCC.C(C)N(C(=O)C1=CC(=NC2=CC=CC=C12)C1=CC=CC=C1)CCCC1CCNCC1 | [CH3:1][CH2:2][N:3]([CH2:4][CH2:5][CH2:6][CH:7]1[CH2:8][CH2:9][N:10]([CH2:36][c:37]2[cH:38][cH:39][cH:40][cH:41][cH:42]2)[CH2:11][CH2:12]1)[C:13](=[O:14])[c:15]1[cH:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]12.O[CH2:34][CH3:35].O=[C:31](Cl)O[CH2:32]C(Cl)(Cl)Cl... | CCN(CCCC1CCN(Cc2ccccc2)CC1)C(=O)c1cc(-c2ccccc2)nc2ccccc12.CCO.O=C(Cl)OCC(Cl)(Cl)Cl | CCN(CCCC1CCNCC1)C(=O)c1cc(-c2ccccc2)nc2ccccc12.CCNCC.Cc1ccccc1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 6e8a800080ef7c022a0cc532d5f2d3ff0b0f67c74dd4469a553776042ba84491 | 8eba20319c343ac1cef825e2b7686b71133feb20f653a9c5de62e9bf6f9a36a3 | O=C(NCCCC1CCNCC1)c1cc(-c2ccccc2)nc2ccccc12.c1ccccc1 | Cl-[C;H0;D3;+0:1](=O)-O-[CH2;D2;+0:2]-C(-Cl)(-Cl)-Cl.O-[CH2;D2;+0:3]-[C;D1;H3:4].[C:5]-[C:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:12]-[C:13]>>[C;D1;H3:4]-[CH2;D2;+0:3]-[#7:14]-[CH2;D2;+0:2]-[CH3;D1;+0:1].[CH3;D1;+0:8]-[c:9](:[c:10]):[c:11].[C:5]-[C:6]-[NH;D2;+0:7]-[C:12]-[C:13] | 174.9 | [{"value": 174.9, "product": "C(C)N(C(=O)C1=CC(=NC2=CC=CC=C12)C1=CC=CC=C1)CCCC1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Debenzylation is carried out as in Example 48, using N-ethyl-N-[3-(1-benzylpiperidin-4-yl)-propyl]-2-phenylquinoline-4-carboxamide (21 g) in toluene (400 ml), 2,2,2-trichloroethyl chloroformate (9 g), and then a 6N aqueous solution of potassium hydroxide (245 ml) and ethanol (550 ml), as the starting materials. After c... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trichloro group.Ether.Primary alcohol.Tertiary amine | Secondary amine.Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccccc1.c1ccc2ncccc2c1.c1ccccc1 | Other | C1(=CC=CC=C1)C | null | null | CCN(CCCC1CCN(Cc2ccccc2)CC1)C(=O)c1cc(-c2ccccc2)nc2ccccc12.CCO.O=C(Cl)OCC(Cl)(Cl)Cl>C1(=CC=CC=C1)C>CCN(CCCC1CCNCC1)C(=O)c1cc(-c2ccccc2)nc2ccccc12.CCNCC.Cc1ccccc1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-dadf8d7dde1b4f6bbc1fb4ee0a4ec3a0 | CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12.OCCC1CCNCC1>>O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCC(CCO)CC1 | C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)OCC.N1CCC(CC1)CCO>>C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)N1CCC(CC1)CCO | CCO[C:2](=[O:1])[c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12.[NH:19]1[CH2:20][CH2:21][CH:22]([CH2:23][CH2:24][OH:25])[CH2:26][CH2:27]1>>[O:1]=[C:2]([c:3]1[n:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[n:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12)[... | CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12.OCCC1CCNCC1 | O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCC(CCO)CC1 | null | null | O | Acylation | Aminolysis of esters | ce8275f1d7811593d008aaa00f9bfc7989dfa4c2d2aff51886f6f1df30984cf4 | fa66342dd118fe5531ba6a998ac8fab92d2b0db4fd04688560eec7d04e9be0e4 | O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCCC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]>>[C:9]-[C:10]-[N;H0;D3;+0:11](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1)-[C:12]-[C:13] | null | [] | null | null | null | null | Ethyl 2-phenylquinazoline-4-carboxylate (1.7 g) and piperidine-4-ethanol (8 g) are heated at 150° C. for 4 hours. After cooling, water is added and the mixture is extracted with ethyl acetate. The organic phase is dried over magnesium sulphate and evaporated to dryness under reduced pressure. The residue is chromatogra... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccc2ncncc2c1.C1CC[NH]CC1 | HO- | O | null | null | CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12.OCCC1CCNCC1>O>O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCC(CCO)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-31e101be202e4ee2915e126485a4ca81 | C1CC2(CCN1)OCCO2.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12>>O=C1CCN(C(=O)c2nc(-c3ccccc3)nc3ccccc23)CC1 | C(CCC)[Li].O1CCOC12CCNCC2.C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)OCC.O>>C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)N1CCC(CC1)=O | C1C[O:1][C:2]2(O1)[CH2:3][CH2:4][NH:5][CH2:24][CH2:25]2.CCO[C:6](=[O:7])[c:8]1[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]12>>[O:1]=[C:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[c:8]2[n:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:17][c:18]3[cH:19][cH:20... | C1CC2(CCN1)OCCO2.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12 | O=C1CCN(C(=O)c2nc(-c3ccccc3)nc3ccccc23)CC1 | null | null | O1CCCC1.CCCCCC | Acylation | OtherReaction | 32f6ce336f5684ffb0daa27d10f74bc4b8cbfa49c875460150fb3fa6f4577f6f | 49f738810605eb02bfb328b7d19ff7d9f9a2a5b340791bbddd54087ce6e9d1a0 | O=C1CCN(C(=O)c2nc(-c3ccccc3)nc3ccccc23)CC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.C1-C-[O;H0;D2;+0:9]-[C;H0;D4;+0:10]2(-O-1)-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-2>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[C;H0;D3;+0:10](=[O;H0;D1;+0:9])-[C:15]-[C:14]-1)-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:... | null | [] | null | null | 30 | MINUTE | A 1.6M solution of butyllithium in hexane (37 ml) is added, under a nitrogen atmosphere and at 0° C., to 1,4-dioxa-8-azaspiro[4,5]decane (7.5 ml) in anhydrous tetrahydrofuran (30 ml). After 30 minutes, a solution of ethyl 2-phenylquinazoline-4-carboxylate (8 g) in anhydrous tetrahydrofuran (30 ml) is added. After 2 hou... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Ether.Secondary amine | Ketone.Tertiary amide | C1CC2(CCN1)OCCO2 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ccc2ncncc2c1 | HO- | O1CCCC1.CCCCCC | null | 0.5 | C1CC2(CCN1)OCCO2.CCOC(=O)c1nc(-c2ccccc2)nc2ccccc12>O1CCCC1.CCCCCC>O=C1CCN(C(=O)c2nc(-c3ccccc3)nc3ccccc23)CC1 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ead41bbcb94746078cae989594ac58b8 | O=C(O)c1cc(-c2ccccc2)nc2c(C(F)(F)F)cccc12.O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCCCC1>>CCN(CC)C(=O)c1cc(-c2ccccc2)nc2c(C(F)(F)F)cccc12 | C1(=CC=CC=C1)C1=NC2=C(C=CC=C2C(=C1)C(=O)O)C(F)(F)F.C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)C(=O)N1CCCCCC1>>C(C)N(C(=O)C1=CC(=NC2=C(C=CC=C12)C(F)(F)F)C1=CC=CC=C1)CC | O[C:6](=[O:7])[c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:17][c:18]2[c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25][cH:26][c:27]12.O=C(c1nc(-c2ccccc2)nc2ccccc12)[N:3]1[CH2:2][CH2:1]CC[CH2:5][CH2:4]1>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[C:6](=[O:7])[c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:1... | O=C(O)c1cc(-c2ccccc2)nc2c(C(F)(F)F)cccc12.O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCCCC1 | CCN(CC)C(=O)c1cc(-c2ccccc2)nc2c(C(F)(F)F)cccc12 | null | null | null | Acylation | OtherReaction | 797d7fa09000ad17659c3ffa22432889b3714226a0a1c23e9eb1f18060ea232a | 98b1cec464b0c16c57f689630d9946f571ff06496ba7b5493db7e3bc31da0906 | c1ccc(-c2ccc3ccccc3n2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.O=C(-[N;H0;D3;+0:9]1-[C:10]-[CH2;D2;+0:11]-C-C-[CH2;D2;+0:12]-[C:13]-1)-c1:n:c(-c2:c:c:c:c:c:2):n:c2:c:c:c:c:c:1:2>>[CH3;D1;+0:11]-[C:10]-[N;H0;D3;+0:9](-[C:13]-[CH3;D1;+0:12])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | null | null | null | null | The 2-phenyl-8-trifluoromethylquinoline-4-carboxylic acid can be prepared by the process described by D. W. BOYKIN et al., J. Med. Chem., 11 (2), 273-277 (1968).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amide | Tertiary amide | c1ccccc1.c1ccc2ncncc2c1.C1CCC[NH]CC1 | null | c1ccccc1.c1ccc2ncccc2c1 | HO- | null | null | null | O=C(O)c1cc(-c2ccccc2)nc2c(C(F)(F)F)cccc12.O=C(c1nc(-c2ccccc2)nc2ccccc12)N1CCCCCC1>>CCN(CC)C(=O)c1cc(-c2ccccc2)nc2c(C(F)(F)F)cccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-c39833f6725448ef840e93d90607c1cb | CC(C)(C)C#CCCO.CNCc1cccc2ccccc12>>CN(CCC#CC(C)(C)C)Cc1cccc2ccccc12 | CS(=O)(=O)Cl.CC(C#CCCO)(C)C.C(C)N(CC)CC.CNCC1=CC=CC2=CC=CC=C12>>CN(CCC#CC(C)(C)C)CC1=CC=CC2=CC=CC=C12 | O[CH2:3][CH2:4][C:5]#[C:6][C:7]([CH3:8])([CH3:9])[CH3:10].[CH3:1][NH:2][CH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12>>[CH3:1][N:2]([CH2:3][CH2:4][C:5]#[C:6][C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12 | CC(C)(C)C#CCCO.CNCc1cccc2ccccc12 | CN(CCC#CC(C)(C)C)Cc1cccc2ccccc12 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | f33a8d71b7dbaa463dcb87d1e5073e084c21a5fbc935ce82a22b6d65293f45d1 | 87693a475e46c41583976158ec46dcaf8be8cc05c5635654a6a68033770f8d5c | c1ccc2ccccc2c1 | O-[CH2;D2;+0:1]-[C:2]-[C:3]#[C:4]-[C:5].[C;D1;H3:6]-[NH;D2;+0:7]-[C:8]-[c:9]>>[C:5]-[C:4]#[C:3]-[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7](-[C;D1;H3:6])-[C:8]-[c:9] | null | [] | null | null | null | null | To a solution of 540 mg 5,5-dimethyl-3-hexyn-1-ol in dimethylformamide (DMF) are added, at 0° 1.2 ml triethylamine. Then are added, dropwise, with stirring, 0.335 ml methanesulfonylchloride. After 2 hours of stirring at room temperature are added 740 mg N-methyl-1-naphthylmethylamine and the mixture is heated overnight... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | null | null | c1ccc2ccccc2c1 | HO- | CN(C=O)C | null | null | CC(C)(C)C#CCCO.CNCc1cccc2ccccc12>CN(C=O)C>CN(CCC#CC(C)(C)C)Cc1cccc2ccccc12 |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-1d756b7823794bab81fbad4ad4cef0f6 | C#CCCN(C)Cc1cccc2ccccc12.CCC(=O)CC>>CCC(O)(C#CCCN(C)Cc1cccc2ccccc12)CC | CN(CCC#C)CC1=CC=CC2=CC=CC=C12.C(CCC)[Li].C(C)C(=O)CC.O1CCCC1>>CN(CCC#CC(CC)(O)CC)CC1=CC=CC2=CC=CC=C12 | [CH:5]#[C:6][CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12.[CH3:1][CH2:2][C:3](=[O:4])[CH2:22][CH3:23]>>[CH3:1][CH2:2][C:3]([OH:4])([C:5]#[C:6][CH2:7][CH2:8][N:9]([CH3:10])[CH2:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]12)[CH2:2... | C#CCCN(C)Cc1cccc2ccccc12.CCC(=O)CC | CCC(O)(C#CCCN(C)Cc1cccc2ccccc12)CC | null | null | CCCCCC | C-C Coupling | OtherReaction | 2ddb79a55c34731f669ca9c81c37bd79ca03c4be0b8aa443046efbe4fb65f2a7 | 77853d31b4fad0a859afba1c4b23a275023e810d45fe8d791ab91aae7d1b14c5 | c1ccc2ccccc2c1 | [C;D1;H3:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C;D1;H3:6].[C:7]-[C:8]#[CH;D1;+0:9]>>[C:7]-[C:8]#[C;H0;D2;+0:9]-[C;H0;D4;+0:3](-[OH;D1;+0:4])(-[C:5]-[C;D1;H3:6])-[C:2]-[C;D1;H3:1] | null | [] | null | null | 3 | HOUR | To 2 g N-methyl-N-(1-naphthylmethyl)-3-butyn-amine in abs. tetrahydrofurane (THF) are added dropwise, at -70°, 5.6 ml of a 15% by weight solution of n-butyllithium in hexane and half an hour later, at -70°, 0.95 ml diethylketone. The mixture is stirred for 3 hours at room temperature, poured onto ice and extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Alkyne | Tertiary alcohol.Alkyne | null | null | c1ccc2ccccc2c1 | null | CCCCCC | null | 3 | C#CCCN(C)Cc1cccc2ccccc12.CCC(=O)CC>CCCCCC>CCC(O)(C#CCCN(C)Cc1cccc2ccccc12)CC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-7529c3f99556424384cd1a0ebf843f7d | CCC(O)(C#CCCN(C)Cc1cccc2ccccc12)CC>>CC=C(C#CCCN(C)Cc1cccc2ccccc12)CC | CN(CCC#CC(CC)(O)CC)CC1=CC=CC2=CC=CC=C12.C(C)N(CC)CC.S(=O)(=O)(C)Cl>>CN(CCC#CC(=CC)CC)CC1=CC=CC2=CC=CC=C12 | O[C:3]([CH2:2][CH3:1])([C:4]#[C:5][CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12)[CH2:21][CH3:22]>>[CH3:1][CH:2]=[C:3]([C:4]#[C:5][CH2:6][CH2:7][N:8]([CH3:9])[CH2:10][c:11]1[cH:12][cH:13][cH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12)[CH2:21][CH3:22] | CCC(O)(C#CCCN(C)Cc1cccc2ccccc12)CC | CC=C(C#CCCN(C)Cc1cccc2ccccc12)CC | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 2552af78a9ee7fee2cf4bc86811ade6ce7c2595ea6de1b1217b4ecd33d9a5077 | 63e4ba80024292782b5f87f96975225484dff39f49e96eea21874ac0cd9091a0 | c1ccc2ccccc2c1 | O-[C;H0;D4;+0:1](-[C:2]-[C;D1;H3:3])(-[C:4]#[C:5]-[C:6])-[CH2;D2;+0:7]-[C;D1;H3:8]>>[C:6]-[C:5]#[C:4]-[C;H0;D3;+0:1](-[C:2]-[C;D1;H3:3])=[CH;D2;+0:7]-[C;D1;H3:8] | null | [] | null | null | 3 | HOUR | To a solution of 630 mg N-methyl-N-(1-naphthylmethyl)-5-ethyl-5-hydroxy-3-heptyn-amine in CH2Cl2 are added, dropwise, at -20° 0.5 ml triethylamine and thereafter 0.21 ml mesylchloride, dissolved in CH2Cl2. The mixture is stirred for 3 hours at room temperature, washed several times with water, the organic phase is drie... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol | null | null | null | c1ccc2ccccc2c1 | HO- | C(Cl)Cl | null | 3 | CCC(O)(C#CCCN(C)Cc1cccc2ccccc12)CC>C(Cl)Cl>CC=C(C#CCCN(C)Cc1cccc2ccccc12)CC |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-ffc039227aef4369869c7baa092e988a | C1=CCCCC1.CC#N.[Cl-].[Hg+2]>>CC(=O)N[C@@H]1CCCC[C@H]1[Hg][Cl] | C1=CCCCC1.[N+](=O)([O-])[O-].[Hg+2].[N+](=O)([O-])[O-].C(C)#N.C(C)#N.[Cl-].[Na+].O>>C(C)(=O)N[C@H]1[C@@H](CCCC1)[Hg]Cl | [CH:5]1=[CH:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[CH3:1][C:2]#[N:4].[Cl-:12].[Hg+2:11]>>[CH3:1][C:2](=[O:3])[NH:4][C@@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@H:10]1[Hg:11][Cl:12] | C1=CCCCC1.CC#N.[Cl-].[Hg+2] | CC(=O)N[C@@H]1CCCC[C@H]1[Hg][Cl] | null | null | null | Functional Group Interconversion | OtherReaction | 6b8c75af294d7635f44730141bbdd26786c057623a0db22e0f682c5d03b5e000 | 7924cfddfbbfa4baeaf3b83901049066d199ee7260bab6d631e0da88fd9399e8 | C1CCCCC1 | [C;D1;H3:1]-[C;H0;D2;+0:2]#[N;H0;D1;+0:3].[C:4]1-[C:5]-[C:6]-[C:7]-[CH;D2;+0:8]=[CH;D2;+0:9]-1.[Cl-;H0;D0:10].[Hg+2;D0:11]>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;D1;H0:12])-[NH;D2;+0:3]-[C@@H;D3;+0:9]1-[C:4]-[C:5]-[C:6]-[C:7]-[C@H;D3;+0:8]-1-[Hg;D2;+0:11]-[Cl;H0;D1;+0:10] | null | [] | null | null | 1 | HOUR | 20 ml (0.2 mole) of cyclohexene in 50 ml of acetonitrile are added dropwise over the course of 20 minutes to a suspension of 65 g (0.2 mole) of mercury(II) nitrate in 150 ml of acetonitrile at 0° C. After 1 hour at room temperature, the yellow solution is poured into a mixture of 100 ml of saturated sodium chloride sol... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Secondary amide | C1=CCCCC1 | C1CCCCC1 | C1CCCCC1 | null | null | null | 1 | C1=CCCCC1.CC#N.[Cl-].[Hg+2]>>CC(=O)N[C@@H]1CCCC[C@H]1[Hg][Cl] |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-9c1a67b4b67e42289524d20455c072ac | C=C(Cl)C#N.CC(=O)N[C@@H]1CCCC[C@H]1[Hg][Cl]>>CC(=O)N[C@@H]1CCCC[C@H]1CC(Cl)C#N | C(C)(=O)N[C@H]1[C@@H](CCCC1)[Hg]Cl.ClC(C#N)=C.[BH4-].[Na+]>>C(C)(=O)N[C@H]1[C@@H](CCCC1)CC(C#N)Cl | [CH2:11]=[C:12]([Cl:13])[C:14]#[N:15].[Cl][Hg][C@H:10]1[C@H:5]([NH:4][C:2]([CH3:1])=[O:3])[CH2:6][CH2:7][CH2:8][CH2:9]1>>[CH3:1][C:2](=[O:3])[NH:4][C@@H:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C@H:10]1[CH2:11][CH:12]([Cl:13])[C:14]#[N:15] | C=C(Cl)C#N.CC(=O)N[C@@H]1CCCC[C@H]1[Hg][Cl] | CC(=O)N[C@@H]1CCCC[C@H]1CC(Cl)C#N | null | null | C(C)O | C-C Coupling | OtherReaction | 465f1e902fe21d80675d40f7ce86a8c1d580b9a21371f1bd530fdeae50d3b194 | 6e201f253d299cba9dce11df416351b338d329a97929620e1451b17f0c1815ea | C1CCCCC1 | [CH2;D1;+0:1]=[C;H0;D3;+0:2](-[Cl;D1;H0:3])-[C:4]#[N;D1;H0:5].[C:6]-[C:7](-[#7:8]-[C:9](-[C;D1;H3:10])=[O;D1;H0:11])-[C@H;D3;+0:12](-[Hg]-[Cl])-[C:13]-[C:14]>>[C:6]-[C:7](-[#7:8]-[C:9](-[C;D1;H3:10])=[O;D1;H0:11])-[C@H;D3;+0:12](-[CH2;D2;+0:1]-[CH;D3;+0:2](-[Cl;D1;H0:3])-[C:4]#[N;D1;H0:5])-[C:13]-[C:14] | null | [] | null | null | null | null | 31 g of trans-1-acetamido-2-chloromercuriocyclohexane are suspended in 250 ml of 95% strength ethanol: 187 ml (4 equivalents) of 2-chloroacrylonitrile are added. While cooling in ice, a solution of 3 g of sodium borohydride in 50 ml of ethanol is added as rapidly as possible. After warming up to room temperature, the p... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Vinyl | Secondary halide | C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | Other | C(C)O | null | null | C=C(Cl)C#N.CC(=O)N[C@@H]1CCCC[C@H]1[Hg][Cl]>C(C)O>CC(=O)N[C@@H]1CCCC[C@H]1CC(Cl)C#N |
ord_dataset-c34472859da14a81bfe0f74e60f15c43 | ord-56e3c6cb28d240338fbb6e5b190866bb | C1=CCCC1.CC#N.[Cl-].[Hg+2]>>CC(=O)N[C@@H]1CCC[C@H]1[Hg][Cl] | C1=CCCC1.[N+](=O)([O-])[O-].[Hg+2].[N+](=O)([O-])[O-].C(C)#N.C(C)#N.[Cl-].[Na+].O>>C(C)(=O)N[C@H]1[C@@H](CCC1)[Hg]Cl | [CH:5]1=[CH:9][CH2:8][CH2:7][CH2:6]1.[CH3:1][C:2]#[N:4].[Cl-:11].[Hg+2:10]>>[CH3:1][C:2](=[O:3])[NH:4][C@@H:5]1[CH2:6][CH2:7][CH2:8][C@H:9]1[Hg:10][Cl:11] | C1=CCCC1.CC#N.[Cl-].[Hg+2] | CC(=O)N[C@@H]1CCC[C@H]1[Hg][Cl] | null | null | null | Functional Group Interconversion | OtherReaction | bb19a27400995396b64734bd68b0a6fa2d26ceeeb3e34605c914bbeea8dd90e3 | 7924cfddfbbfa4baeaf3b83901049066d199ee7260bab6d631e0da88fd9399e8 | C1CCCC1 | [C;D1;H3:1]-[C;H0;D2;+0:2]#[N;H0;D1;+0:3].[C:4]1-[C:5]-[C:6]-[CH;D2;+0:7]=[CH;D2;+0:8]-1.[Cl-;H0;D0:9].[Hg+2;D0:10]>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;D1;H0:11])-[NH;D2;+0:3]-[C@@H;D3;+0:8]1-[C:4]-[C:5]-[C:6]-[C@H;D3;+0:7]-1-[Hg;D2;+0:10]-[Cl;H0;D1;+0:9] | null | [] | null | null | 1 | HOUR | 10 ml of cyclopentene in 30 ml of acetonitrile are added dropwise to a suspension of 38.3 g of mercury(II) nitrate in 80 ml of acetonitrile at 0° C. After 1 hour at room temperature, the mixture is poured into a mixture of 60 ml of saturated sodium chloride solution and 250 ml of water, and the solid is filtered off wi... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Secondary amide | C1=CCCC1 | C1CCCC1 | C1CCCC1 | null | null | null | 1 | C1=CCCC1.CC#N.[Cl-].[Hg+2]>>CC(=O)N[C@@H]1CCC[C@H]1[Hg][Cl] |
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