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-c31cb9b44c404c10ba3aa533aa079e2b | ord-7a86aea570d147d8ac34221cd31e40e6 | CCO.Nc1cc(Cl)c(C(F)(F)F)cc1[N+](=O)[O-]>>CCOc1cc(N)c([N+](=O)[O-])cc1C(F)(F)F | ClC=1C(=CC(=C(C1)N)[N+](=O)[O-])C(F)(F)F.Cl.CCO.[K].[K]>>C(C)OC=1C(=CC(=C(C1)N)[N+](=O)[O-])C(F)(F)F | [CH3:1][CH2:2][OH:3].Cl[c:4]1[cH:5][c:6]([NH2:7])[c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[C:14]([F:15])([F:16])[F:17]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([NH2:7])[c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]1[C:14]([F:15])([F:16])[F:17] | CCO.Nc1cc(Cl)c(C(F)(F)F)cc1[N+](=O)[O-] | CCOc1cc(N)c([N+](=O)[O-])cc1C(F)(F)F | null | null | O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].[C;D1;H3:10]-[C:11]-[OH;D1;+0:12]>>[C;D1;H3:10]-[C:11]-[O;H0;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9] | 96 | [{"value": 96.0, "product": "C(C)OC=1C(=CC(=C(C1)N)[N+](=O)[O-])C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To EtOH (500 mL) was added potassium metal (ca. 21 g, ca. 537 mmol) and the vigorous reaction had to be cooled with an ice bath. Stirring was continued until all potassium metal was dissolved. Solid commercially available 5-chloro-2-nitro-4-trifluoromethyl-phenylamine [CAS-No. 35375-74-7] (57.74 g, 240 mmol) was added ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | O | null | null | CCO.Nc1cc(Cl)c(C(F)(F)F)cc1[N+](=O)[O-]>O>CCOc1cc(N)c([N+](=O)[O-])cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6668ed22718946af8d9982fae3073955 | CCOc1cc(Br)c([N+](=O)[O-])cc1C(F)(F)F>>CCOc1cc(C#N)c([N+](=O)[O-])cc1C(F)(F)F | BrC1=C(C=C(C(=C1)OCC)C(F)(F)F)[N+](=O)[O-].C(#N)[Cu].Cl>>C(C)OC=1C(=CC(=C(C#N)C1)[N+](=O)[O-])C(F)(F)F | Br[c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:14]([C:15]([F:16])([F:17])[F:18])[cH:13][c:9]1[N+:10](=[O:11])[O-:12]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C:7]#[N:8])[c:9]([N+:10](=[O:11])[O-:12])[cH:13][c:14]1[C:15]([F:16])([F:17])[F:18] | CCOc1cc(Br)c([N+](=O)[O-])cc1C(F)(F)F | CCOc1cc(C#N)c([N+](=O)[O-])cc1C(F)(F)F | null | null | CN1CCCC1=O | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C:7]#[N;D1;H0:8]):[c:2]:[c:3] | 91.2 | [{"value": 91.0, "product": "C(C)OC=1C(=CC(=C(C#N)C1)[N+](=O)[O-])C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "C(C)OC=1C(=CC(=C(C#N)C1)[N+](=O)[O-])C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | A mixture of 1-bromo-5-ethoxy-2-nitro-4-trifluoromethyl-benzene from step 2 (61.81 g, 197 mmol) and CuCN (18.51 g, 207 mmol) in NMP (197 mL) was heated to 150° C. for 30 min. Cooled to 23° C., poured into 1 N HCl, extracted with TBME, washed with brine, dried over Na2SO4. Removal of the solvent in vacuum left a brown o... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | CN1CCCC1=O | 150 | null | CCOc1cc(Br)c([N+](=O)[O-])cc1C(F)(F)F>CN1CCCC1=O>CCOc1cc(C#N)c([N+](=O)[O-])cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f3727613330d4214a86ff7b02415171d | CCOc1cc(C#N)c([N+](=O)[O-])cc1C(F)(F)F>>CCOc1cc(C#N)c(N)cc1C(F)(F)F | C(C)OC=1C(=CC(=C(C#N)C1)[N+](=O)[O-])C(F)(F)F>>NC1=C(C#N)C=C(C(=C1)C(F)(F)F)OCC | O=[N+:10]([O-])[c:9]1[c:6]([C:7]#[N:8])[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:12]([C:13]([F:14])([F:15])[F:16])[cH:11]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C:7]#[N:8])[c:9]([NH2:10])[cH:11][c:12]1[C:13]([F:14])([F:15])[F:16] | CCOc1cc(C#N)c([N+](=O)[O-])cc1C(F)(F)F | CCOc1cc(C#N)c(N)cc1C(F)(F)F | null | [Fe] | Cl.CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 84 | [{"value": 84.0, "product": "NC1=C(C#N)C=C(C(=C1)C(F)(F)F)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.0, "product": "NC1=C(C#N)C=C(C(=C1)C(F)(F)F)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 1 | HOUR | Iron powder (40.96 g, 733 mmol) was added in small portions over 5 min to a stirred suspension of finely grinded 5-ethoxy-2-nitro-4-trifluoromethyl-benzonitrile from step 3 (42.79 g, 164.5 mmol) in MeOH (85 mL) and conc. HCl (102 mL) with water bath cooling keeping the internal temperature at 40-50° C. The resulting mi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Fe].Cl.CO | 50 | 1 | CCOc1cc(C#N)c([N+](=O)[O-])cc1C(F)(F)F>[Fe].Cl.CO>CCOc1cc(C#N)c(N)cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0c6406eebd8a4dddbfbfaaf8027b0b7f | CCOc1cc(C#N)c(N)cc1C(F)(F)F>>CCOc1cc(C#N)ccc1C(F)(F)F | NC1=C(C#N)C=C(C(=C1)C(F)(F)F)OCC.N(=O)OCCC(C)C>>C(C)OC=1C=C(C#N)C=CC1C(F)(F)F | N[c:9]1[c:6]([C:7]#[N:8])[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:11]([C:12]([F:13])([F:14])[F:15])[cH:10]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C:7]#[N:8])[cH:9][cH:10][c:11]1[C:12]([F:13])([F:14])[F:15] | CCOc1cc(C#N)c(N)cc1C(F)(F)F | CCOc1cc(C#N)ccc1C(F)(F)F | null | null | C1CCOC1.C(=O)(O)[O-].[Na+] | Reduction | OtherReaction | a069304de6b46c6d557b2e80c544464adc3bb98001f26c098e87c25f29d552f9 | a4f16f822d2806606c05d0c4baa1761ad37a11006840dde863a01a253bdff5dd | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[cH;D2;+0:1]:[c:2]:[c:3] | 85 | [{"value": 85.0, "product": "C(C)OC=1C=C(C#N)C=CC1C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.8, "product": "C(C)OC=1C=C(C#N)C=CC1C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-amino-5-ethoxy-4-trifluoromethyl-benzonitrile from step 4 (31.62 g, 137.4 mmol) in dry THF (410 mL) was added isoamyl nitrite (40.4 mL, 302 mmol) and the mixture was refluxed for 16 h. The solvent was removed in vacuum to give an orange oil, which was dissolved in sat. NaHCO3-sol., extracted three ti... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C1CCOC1.C(=O)(O)[O-].[Na+] | null | null | CCOc1cc(C#N)c(N)cc1C(F)(F)F>C1CCOC1.C(=O)(O)[O-].[Na+]>CCOc1cc(C#N)ccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0fc3c78d82274405a5f85b70ca28e286 | CCOc1cc(C#N)ccc1C(F)(F)F>>CCOc1cc(C(C)=O)ccc1C(F)(F)F | C1CCOC1.C(C)OC=1C=C(C#N)C=CC1C(F)(F)F.C(C)(C)(C)[Si](Cl)(C)C.C[Mg]Br.C(C)OCC.[NH4+].[Cl-]>>C(C)OC=1C=C(C=CC1C(F)(F)F)C(C)=O | N#[C:7][c:6]1[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:12]([C:13]([F:14])([F:15])[F:16])[cH:11][cH:10]1>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6]([C:7]([CH3:8])=[O:9])[cH:10][cH:11][c:12]1[C:13]([F:14])([F:15])[F:16] | CCOc1cc(C#N)ccc1C(F)(F)F | CCOc1cc(C(C)=O)ccc1C(F)(F)F | null | [Cu]Br | null | Miscellaneous | OtherReaction | 54622de249eb9a5622e28710a02d261b08e09c3ee957106ef84a0e4751ccb30f | 957d5e0aaa82a4f5b73d699040cb2acd7f615417c9e400cbb7a63fa4c133449a | c1ccccc1 | N#[C;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[C;D1;H3:5]-[C;H0;D3;+0:1](=[O;D1;H0:6])-[c:2](:[c:3]):[c:4] | 34 | [{"value": 34.0, "product": "C(C)OC=1C=C(C=CC1C(F)(F)F)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | -70 | CELSIUS | 10 | MINUTE | To a solution of 3-ethoxy-4-trifluoromethyl-benzonitrile from step 5 (5.00 g, 23.2 mmol), copper(I) bromide (100 mg, 0.7 mmol), tert.-butyldimethylchlorosilane (4.20 g, 27.9 mmol) in dry THF (30 mL) at −70° C. was drop wise added a 3 M methylmagnesium bromide solution in diethyl ether (13.2 mL, 39.6 mmol). The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Ketone | null | null | c1ccccc1 | null | [Cu]Br | -70 | 0.166667 | CCOc1cc(C#N)ccc1C(F)(F)F>[Cu]Br>CCOc1cc(C(C)=O)ccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0b933df548924165ac79744b3484814b | Nc1cc(Cl)c(C(F)(F)F)cc1[N+](=O)[O-].OCC(F)(F)F>>Nc1cc(OCC(F)(F)F)c(C(F)(F)F)cc1[N+](=O)[O-] | Cl.FC(CO)(F)F.ClC=1C(=CC(=C(C1)N)[N+](=O)[O-])C(F)(F)F.[OH-].[K+]>>[N+](=O)([O-])C1=C(C=C(C(=C1)C(F)(F)F)OCC(F)(F)F)N | Cl[c:4]1[cH:3][c:2]([NH2:1])[c:17]([N+:18](=[O:19])[O-:20])[cH:16][c:11]1[C:12]([F:13])([F:14])[F:15].[OH:5][CH2:6][C:7]([F:8])([F:9])[F:10]>>[NH2:1][c:2]1[cH:3][c:4]([O:5][CH2:6][C:7]([F:8])([F:9])[F:10])[c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][c:17]1[N+:18](=[O:19])[O-:20] | Nc1cc(Cl)c(C(F)(F)F)cc1[N+](=O)[O-].OCC(F)(F)F | Nc1cc(OCC(F)(F)F)c(C(F)(F)F)cc1[N+](=O)[O-] | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccccc1 | Cl-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].[F;D1;H0:10]-[C:11](-[F;D1;H0:12])(-[F;D1;H0:13])-[C:14]-[OH;D1;+0:15]>>[F;D1;H0:10]-[C:11](-[F;D1;H0:12])(-[F;D1;H0:13])-[C:14]-[O;H0;D2;+0:15]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):... | 98 | [{"value": 98.0, "product": "[N+](=O)([O-])C1=C(C=C(C(=C1)C(F)(F)F)OCC(F)(F)F)N", "details": "PERCENTYIELD", "is_desired": false}] | 23 | CELSIUS | 4 | DAY | Commercially available 5-chloro-2-nitro-4-trifluoromethyl-phenylamine [CAS-No. 35375-74-7] (72.2 g, 300 mmol) was dissolved in DMSO (600 mL) and 2,2,2-trifluoroethanol (270 mL) were added at 23° C., the slightly exothermic reaction was cooled with a ice bath. KOH (85%, 99.0 g, 1500 mmol) were added slowly and the dark ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | O.CS(=O)C | 23 | 96 | Nc1cc(Cl)c(C(F)(F)F)cc1[N+](=O)[O-].OCC(F)(F)F>O.CS(=O)C>Nc1cc(OCC(F)(F)F)c(C(F)(F)F)cc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e2ef43922434b4383fbb884d8e7649e | O=[N+]([O-])c1cc(C(F)(F)F)c(OCC(F)(F)F)cc1Br>>N#Cc1cc(OCC(F)(F)F)c(C(F)(F)F)cc1[N+](=O)[O-] | BrC1=C(C=C(C(=C1)OCC(F)(F)F)C(F)(F)F)[N+](=O)[O-].C(#N)[Cu].Cl>>[N+](=O)([O-])C1=C(C#N)C=C(C(=C1)C(F)(F)F)OCC(F)(F)F | Br[c:3]1[cH:4][c:5]([O:6][CH2:7][C:8]([F:9])([F:10])[F:11])[c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][c:18]1[N+:19](=[O:20])[O-:21]>>[N:1]#[C:2][c:3]1[cH:4][c:5]([O:6][CH2:7][C:8]([F:9])([F:10])[F:11])[c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][c:18]1[N+:19](=[O:20])[O-:21] | O=[N+]([O-])c1cc(C(F)(F)F)c(OCC(F)(F)F)cc1Br | N#Cc1cc(OCC(F)(F)F)c(C(F)(F)F)cc1[N+](=O)[O-] | null | null | CN1CCCC1=O | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[#7;+:5]):[c:6]>>[#7;+:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C:7]#[N;D1;H0:8]):[c:2]:[c:3] | 85 | [{"value": 85.0, "product": "[N+](=O)([O-])C1=C(C#N)C=C(C(=C1)C(F)(F)F)OCC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.6, "product": "[N+](=O)([O-])C1=C(C#N)C=C(C(=C1)C(F)(F)F)OCC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | null | null | A mixture of 1-bromo-2-nitro-5-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-benzene from step 2 (30.54 g, 83.0 mmol) and CuCN (7.80 g, 87.1 mmol) in NMP (83 mL) was heated to 150° C. for 30 min. Cooled to 23° C., poured into 1 N HCl, extracted with EtOAc, washed with brine, dried over Na2SO4. Removal of the solvent in va... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | CN1CCCC1=O | 150 | null | O=[N+]([O-])c1cc(C(F)(F)F)c(OCC(F)(F)F)cc1Br>CN1CCCC1=O>N#Cc1cc(OCC(F)(F)F)c(C(F)(F)F)cc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6123c6982ce24b7ea88eee8dc137d7fe | N#Cc1cc(OCC(F)(F)F)c(C(F)(F)F)cc1[N+](=O)[O-]>>N#Cc1cc(OCC(F)(F)F)c(C(F)(F)F)cc1N | [N+](=O)([O-])C1=C(C#N)C=C(C(=C1)C(F)(F)F)OCC(F)(F)F>>NC1=C(C#N)C=C(C(=C1)C(F)(F)F)OCC(F)(F)F | O=[N+:19]([O-])[c:18]1[c:3]([C:2]#[N:1])[cH:4][c:5]([O:6][CH2:7][C:8]([F:9])([F:10])[F:11])[c:12]([C:13]([F:14])([F:15])[F:16])[cH:17]1>>[N:1]#[C:2][c:3]1[cH:4][c:5]([O:6][CH2:7][C:8]([F:9])([F:10])[F:11])[c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][c:18]1[NH2:19] | N#Cc1cc(OCC(F)(F)F)c(C(F)(F)F)cc1[N+](=O)[O-] | N#Cc1cc(OCC(F)(F)F)c(C(F)(F)F)cc1N | null | [Fe] | Cl.CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 88.6 | [{"value": 84.0, "product": "NC1=C(C#N)C=C(C(=C1)C(F)(F)F)OCC(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.6, "product": "NC1=C(C#N)C=C(C(=C1)C(F)(F)F)OCC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 30 | CELSIUS | 1 | HOUR | Iron powder (15.80 g, 283.0 mmol) was added in small portions over 5 min to a stirred suspension of finely grinded 2-nitro-5-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-benzonitrile from step 3 (19.93 g, 63.4 mmol) in MeOH (32 mL) and conc. HCl (40 mL) with water bath cooling keeping the internal temperature at 25-35° C... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Fe].Cl.CO | 30 | 1 | N#Cc1cc(OCC(F)(F)F)c(C(F)(F)F)cc1[N+](=O)[O-]>[Fe].Cl.CO>N#Cc1cc(OCC(F)(F)F)c(C(F)(F)F)cc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5226494be78e4086bc813be3e33f6b6a | N#Cc1cc(OCC(F)(F)F)c(C(F)(F)F)cc1N>>N#Cc1ccc(C(F)(F)F)c(OCC(F)(F)F)c1 | NC1=C(C#N)C=C(C(=C1)C(F)(F)F)OCC(F)(F)F.N(=O)OCCC(C)C>>FC(COC=1C=C(C#N)C=CC1C(F)(F)F)(F)F | N[c:4]1[c:3]([C:2]#[N:1])[cH:18][c:11]([O:12][CH2:13][C:14]([F:15])([F:16])[F:17])[c:6]([C:7]([F:8])([F:9])[F:10])[cH:5]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[c:11]([O:12][CH2:13][C:14]([F:15])([F:16])[F:17])[cH:18]1 | N#Cc1cc(OCC(F)(F)F)c(C(F)(F)F)cc1N | N#Cc1ccc(C(F)(F)F)c(OCC(F)(F)F)c1 | null | null | CC(C)(C)OC.C1CCOC1 | Reduction | OtherReaction | a069304de6b46c6d557b2e80c544464adc3bb98001f26c098e87c25f29d552f9 | a4f16f822d2806606c05d0c4baa1761ad37a11006840dde863a01a253bdff5dd | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7]>>[N;D1;H0:6]#[C:5]-[c:4](:[c:7]):[cH;D2;+0:1]:[c:2]:[c:3] | 79.1 | [{"value": 79.0, "product": "FC(COC=1C=C(C#N)C=CC1C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.1, "product": "FC(COC=1C=C(C#N)C=CC1C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-amino-5-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-benzonitrile from step 4 (14.47 g, 50.9 mmol) in dry THF (153 mL) was added isoamyl nitrite (15.0 mL, 112.0 mmol) and the mixture was refluxed for 20 h. The solvent was removed in vacuum to give an orange oil, which was dissolved in TBME, washed with... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | CC(C)(C)OC.C1CCOC1 | null | null | N#Cc1cc(OCC(F)(F)F)c(C(F)(F)F)cc1N>CC(C)(C)OC.C1CCOC1>N#Cc1ccc(C(F)(F)F)c(OCC(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d0b6ad5b81f243ac9115f220090f3ec4 | CNOC.O=C(O)c1ccc(C(F)(F)F)c(OCC(F)(F)F)c1>>CON(C)C(=O)c1ccc(C(F)(F)F)c(OCC(F)(F)F)c1 | FC(COC=1C=C(C(=O)O)C=CC1C(F)(F)F)(F)F.Cl.CNOC.CN1CCOCC1.Cl.CN(CCCN=C=NCC)C>>CON(C(C1=CC(=C(C=C1)C(F)(F)F)OCC(F)(F)F)=O)C | [CH3:1][O:2][NH:3][CH3:4].O[C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[c:15]([O:16][CH2:17][C:18]([F:19])([F:20])[F:21])[cH:22]1>>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[c:7]1[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[c:15]([O:16][CH2:17][C:18]([F:19])([F:20])[F:21])[cH:22]1 | CNOC.O=C(O)c1ccc(C(F)(F)F)c(OCC(F)(F)F)c1 | CON(C)C(=O)c1ccc(C(F)(F)F)c(OCC(F)(F)F)c1 | null | CN(C)C=1C=CN=CC1 | CN(C)C=O.C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[#8:7]-[NH;D2;+0:8]-[C;D1;H3:9]>>[C;D1;H3:6]-[#8:7]-[N;H0;D3;+0:8](-[C;D1;H3:9])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | 23 | CELSIUS | 18 | HOUR | To a mixture of 3-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-benzoic acid from step 6 (9.22 g, 32 mmol), N,O-dimethylhydroxylamine hydrochloride (5.00 g, 51 mmol), N-methylmorpholine (5.62 mL, 51 mmol) and 4-DMAP (391 mg, 3.2 mmol) in DCM (100 mL) and DMF (20 mL) at 0° C. was added 1-(3-dimethylaminopropyl)-3-ethylcarb... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.CN(C)C=O.C(Cl)Cl | 23 | 18 | CNOC.O=C(O)c1ccc(C(F)(F)F)c(OCC(F)(F)F)c1>CN(C)C=1C=CN=CC1.CN(C)C=O.C(Cl)Cl>CON(C)C(=O)c1ccc(C(F)(F)F)c(OCC(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d7b3ab1111c646a79a1d48f178e89544 | CON(C)C(=O)c1ccc(C(F)(F)F)c(OCC(F)(F)F)c1>>CC(=O)c1ccc(C(F)(F)F)c(OCC(F)(F)F)c1 | Cl.CON(C(C1=CC(=C(C=C1)C(F)(F)F)OCC(F)(F)F)=O)C.C[Mg]Br>>FC(COC=1C=C(C=CC1C(F)(F)F)C(C)=O)(F)F | CON(C)[C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[c:12]([O:13][CH2:14][C:15]([F:16])([F:17])[F:18])[cH:19]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[c:12]([O:13][CH2:14][C:15]([F:16])([F:17])[F:18])[cH:19]1 | CON(C)C(=O)c1ccc(C(F)(F)F)c(OCC(F)(F)F)c1 | CC(=O)c1ccc(C(F)(F)F)c(OCC(F)(F)F)c1 | null | null | CC(C)(C)OC.C1CCOC1 | Functional Group Interconversion | OtherReaction | 0e1b501f4aadb0e84ffc93b33216cc37dfe617cb6c3e325779c58539a7f5c4e4 | af85307a4412ed48cedcfde84079732215472ffbe274bdc1dc12e9979d5c5e06 | c1ccccc1 | C-O-N(-C)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]>>[C;D1;H3:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 15 | MINUTE | To a solution of N-methoxy-N-methyl-3-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-benzamide from step 7 (10.467 g, 32 mmol) in THF (100 mL) at −5° C. was added methylmagnesium bromide (3 M in Et2O, 21.1 mL, 64 mmol). The mixture was stirred at 0° C. for 15 min, then warmed up to 23° C., stirring was continued for furthe... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide | Ketone | null | null | c1ccccc1 | HO- | CC(C)(C)OC.C1CCOC1 | 0 | 0.25 | CON(C)C(=O)c1ccc(C(F)(F)F)c(OCC(F)(F)F)c1>CC(C)(C)OC.C1CCOC1>CC(=O)c1ccc(C(F)(F)F)c(OCC(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c23b3d2a99514976af14dec6b79f1d14 | N#Cc1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12.NO>>N=C(NO)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | FC(C1=CC(=NC=2N1N=CC2C#N)C2=CC=C(C=C2)C(F)(F)F)(F)F.Cl.NO.C([O-])([O-])=O.[K+].[K+]>>ONC(=N)C=1C=NN2C1N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F | [N:1]#[C:2][c:5]1[cH:6][n:7][n:8]2[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][c:15](-[c:16]3[cH:17][cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]3)[n:26][c:27]12.[NH2:3][OH:4]>>[NH:1]=[C:2]([NH:3][OH:4])[c:5]1[cH:6][n:7][n:8]2[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][c:15](-[c:16]3[cH:17][cH:18][c:19]([C:20]... | N#Cc1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12.NO | N=C(NO)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-hydroxyimidamide from nitrile and hydroxylamine | 08a01a2d1cd9346f7b3dddbfcbf8124b349e5763794287a4a1b9ee287b4d6aa7 | 38c3b778e04536ea6155ce05fc7c4746354a32b3703099defb07490833e3a961 | c1ccc(-c2ccn3nccc3n2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3]1:[c:4]:[#7;a:5]:[#7;a:6](:[c:7]):[c:8]:1:[#7;a:9]:[c:10].[NH2;D1;+0:11]-[O;D1;H1:12]>>[NH;D1;+0:1]=[C;H0;D3;+0:2](-[NH;D2;+0:11]-[O;D1;H1:12])-[c:3]1:[c:4]:[#7;a:5]:[#7;a:6](:[c:7]):[c:8]:1:[#7;a:9]:[c:10] | 69.1 | [{"value": 69.0, "product": "ONC(=N)C=1C=NN2C1N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.1, "product": "ONC(=N)C=1C=NN2C1N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carbonitrile [CAS-No. 851262-50-5] (2.0 g, 5.61 mmol), hydroxylamine hydrochloride (0.78 g, 11.2 mmol) and potassium carbonate (2.33 g, 16.8 mmol) in ethanol (100 ml) was heated under reflux conditions for 3 h. After the rea... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Secondary amine | null | null | c1cnc2ccnn2c1.c1ccccc1 | null | C(C)O | null | null | N#Cc1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12.NO>C(C)O>N=C(NO)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c541337de22b4c3ba4b3ff8e6787cae7 | N#Cc1ccc(S(N)(=O)=O)s1.NO>>N=C(NO)c1ccc(S(N)(=O)=O)s1 | S(N)(=O)(=O)C1=CC=C(S1)C#N.Cl.NO.C([O-])([O-])=O.[Na+].[Na+]>>ONC(=N)C=1SC(=CC1)S(N)(=O)=O | [N:1]#[C:2][c:5]1[cH:6][cH:7][c:8]([S:9]([NH2:10])(=[O:11])=[O:12])[s:13]1.[NH2:3][OH:4]>>[NH:1]=[C:2]([NH:3][OH:4])[c:5]1[cH:6][cH:7][c:8]([S:9]([NH2:10])(=[O:11])=[O:12])[s:13]1 | N#Cc1ccc(S(N)(=O)=O)s1.NO | N=C(NO)c1ccc(S(N)(=O)=O)s1 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | N-hydroxyimidamide from nitrile and hydroxylamine | 08a01a2d1cd9346f7b3dddbfcbf8124b349e5763794287a4a1b9ee287b4d6aa7 | 38c3b778e04536ea6155ce05fc7c4746354a32b3703099defb07490833e3a961 | c1ccsc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[#16;a:5]:[c:6].[NH2;D1;+0:7]-[O;D1;H1:8]>>[NH;D1;+0:1]=[C;H0;D3;+0:2](-[NH;D2;+0:7]-[O;D1;H1:8])-[c:3](:[c:4]):[#16;a:5]:[c:6] | 58 | [{"value": 58.0, "product": "ONC(=N)C=1SC(=CC1)S(N)(=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.5, "product": "ONC(=N)C=1SC(=CC1)S(N)(=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 5-sulfamoyl-thiophene-2-carbonitrile [CAS-No. 519055-65-3] (0.31 g, 1.65 mmol), hydroxylamine hydrochloride (0.23 g, 3.31 mmol) and sodium carbonate (0.175 g, 1.65 mmol) in water (4.6 ml) and ethanol (1 ml) was heated under reflux conditions for 1.5 h. The reaction mixture was poured into water (50... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Secondary amine | null | null | c1ccsc1 | null | O.C(C)O | null | null | N#Cc1ccc(S(N)(=O)=O)s1.NO>O.C(C)O>N=C(NO)c1ccc(S(N)(=O)=O)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6975fa515ba4400b8ffc0b36dae7d9f5 | N#Cc1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12.NO>>N=C(NO)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | FC(C1=CC(=NC=2N1C=NC2C#N)C2=CC=C(C=C2)C(F)(F)F)(F)F.Cl.NO.C([O-])([O-])=O.[K+].[K+]>>ONC(=N)C=1N=CN2C1N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F | [N:1]#[C:2][c:5]1[n:6][cH:7][n:8]2[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][c:15](-[c:16]3[cH:17][cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]3)[n:26][c:27]12.[NH2:3][OH:4]>>[NH:1]=[C:2]([NH:3][OH:4])[c:5]1[n:6][cH:7][n:8]2[c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][c:15](-[c:16]3[cH:17][cH:18][c:19]([C:20]... | N#Cc1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12.NO | N=C(NO)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-hydroxyimidamide from nitrile and hydroxylamine | 08a01a2d1cd9346f7b3dddbfcbf8124b349e5763794287a4a1b9ee287b4d6aa7 | 38c3b778e04536ea6155ce05fc7c4746354a32b3703099defb07490833e3a961 | c1ccc(-c2ccn3cncc3n2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[#7;a:9]:[c:10].[NH2;D1;+0:11]-[O;D1;H1:12]>>[NH;D1;+0:1]=[C;H0;D3;+0:2](-[NH;D2;+0:11]-[O;D1;H1:12])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6](:[c:7]):[c:8]:1:[#7;a:9]:[c:10] | 20.3 | [{"value": 20.0, "product": "ONC(=N)C=1N=CN2C1N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.3, "product": "ONC(=N)C=1N=CN2C1N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of 4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carbonitrile [CAS-No. 851263-42-8] 1.16 g, 3.26 mmol), hydroxylamine hydrochloride (0.46 g, 6.62 mmol) and potassium carbonate (1.35 g, 9.77 mmol) in ethanol (50 ml) was heated under reflux conditions for 3 h. The precipitate... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Secondary amine | null | null | c1cnc2cncn2c1.c1ccccc1 | null | C(C)O | null | null | N#Cc1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12.NO>C(C)O>N=C(NO)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-59dde58bc7994ddbbdeac85cde14172f | N#Cc1ccc(N)nc1>>NC(=O)c1ccc(N)nc1 | NC1=NC=C(C=C1)C#N.Cl.NO.C([O-])([O-])=O.[Na+].[Na+]>>NC1=NC=C(C(=O)N)C=C1 | [N:1]#[C:2][c:4]1[cH:5][cH:6][c:7]([NH2:8])[n:9][cH:10]1>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([NH2:8])[n:9][cH:10]1 | N#Cc1ccc(N)nc1 | NC(=O)c1ccc(N)nc1 | null | null | O.C(C)O | Functional Group Addition | Nitrile to amide | 538c271df55faf6c40eed3b4a4f85f3f4e5c19a479326ea2f666ed82bd9b2b69 | 276fda5d5f5a53d66ac109e4f504751b1c2e3eef2b30a60eb746c3377c075030 | c1ccncc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[NH2;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:8])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 24.1 | [{"value": 24.1, "product": "NC1=NC=C(C(=O)N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of commercially available 2-amino-5-cyano-pyridine [CAS-No. 4214-73-7] (5.0 g, 42 mmol), hydroxylamine hydrochloride (17.5 g, 0.25 mol) and sodium carbonate (31.1 g, 0.29 mol) in water (95 ml) and ethanol (21 ml) was heated under reflux conditions for 6 h. The reaction mixture was poured into water (1... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | c1ccncc1 | Other | O.C(C)O | null | null | N#Cc1ccc(N)nc1>O.C(C)O>NC(=O)c1ccc(N)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ad98dbee76b940c0b568555a0efcb318 | N#Cc1cnc(N)nc1.NO>>N=C(NO)c1cnc(N)nc1 | NC1=NC=C(C=N1)C#N.Cl.NO.C([O-])([O-])=O.[K+].[K+]>>NC1=NC=C(C=N1)C(=N)NO | [N:1]#[C:2][c:5]1[cH:6][n:7][c:8]([NH2:9])[n:10][cH:11]1.[NH2:3][OH:4]>>[NH:1]=[C:2]([NH:3][OH:4])[c:5]1[cH:6][n:7][c:8]([NH2:9])[n:10][cH:11]1 | N#Cc1cnc(N)nc1.NO | N=C(NO)c1cnc(N)nc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | N-hydroxyimidamide from nitrile and hydroxylamine | 08a01a2d1cd9346f7b3dddbfcbf8124b349e5763794287a4a1b9ee287b4d6aa7 | 38c3b778e04536ea6155ce05fc7c4746354a32b3703099defb07490833e3a961 | c1cncnc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1.[NH2;D1;+0:9]-[O;D1;H1:10]>>[NH;D1;+0:1]=[C;H0;D3;+0:2](-[NH;D2;+0:9]-[O;D1;H1:10])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1 | 72.1 | [{"value": 72.0, "product": "NC1=NC=C(C=N1)C(=N)NO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "NC1=NC=C(C=N1)C(=N)NO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred mixture of commercially available 2-amino-5-cyano-pyrimidine [CAS-No. 1753-48-6] (1.39 g, 11.6 mmol), hydroxylamine hydrochloride (1.61 g, 23.2 mol) and potassium carbonate (4.8 g, 34.7 mol) in ethanol (57 ml) was heated under reflux conditions for 3 h. The reaction mixture was evaporated and purified by colu... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Secondary amine | null | null | c1cncnc1 | null | C(C)O | null | null | N#Cc1cnc(N)nc1.NO>C(C)O>N=C(NO)c1cnc(N)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-23fc2512cf304762b3cda44243edf4a0 | N#Cc1ccnc(N)c1.NO>>N=C(NO)c1ccnc(N)c1 | NC1=NC=CC(=C1)C#N.Cl.NO.C([O-])([O-])=O.[Na+].[Na+]>>NC1=NC=CC(=C1)C(=N)NO | [N:1]#[C:2][c:5]1[cH:6][cH:7][n:8][c:9]([NH2:10])[cH:11]1.[NH2:3][OH:4]>>[NH:1]=[C:2]([NH:3][OH:4])[c:5]1[cH:6][cH:7][n:8][c:9]([NH2:10])[cH:11]1 | N#Cc1ccnc(N)c1.NO | N=C(NO)c1ccnc(N)c1 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | N-hydroxyimidamide from nitrile and hydroxylamine | 08a01a2d1cd9346f7b3dddbfcbf8124b349e5763794287a4a1b9ee287b4d6aa7 | 38c3b778e04536ea6155ce05fc7c4746354a32b3703099defb07490833e3a961 | c1ccncc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1.[NH2;D1;+0:9]-[O;D1;H1:10]>>[NH;D1;+0:1]=[C;H0;D3;+0:2](-[NH;D2;+0:9]-[O;D1;H1:10])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | 68.2 | [{"value": 68.0, "product": "NC1=NC=CC(=C1)C(=N)NO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.2, "product": "NC1=NC=CC(=C1)C(=N)NO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A stirred mixture of commercially available 2-amino-4-cyano-pyridine [CAS-No. 42182-27-4] (1.0 g, 8.39 mmol), hydroxylamine hydrochloride (1.17 g, 16.8 mmol) and sodium carbonate (0.89 g, 8.39 mol) in water (8 ml) and ethanol (16 ml) was heated under reflux conditions for 3 h. The reaction mixture was evaporated, water... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Secondary amine | null | null | c1ccncc1 | null | O.C(C)O | null | 1 | N#Cc1ccnc(N)c1.NO>O.C(C)O>N=C(NO)c1ccnc(N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b91f482d46e44f348a4614e2bcd0e8b7 | CCOC(=O)c1c[nH]nc1N.O=C(CC(=O)C(F)F)c1ccc(C(F)(F)F)cc1>>O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | S(O)(O)(=O)=O.CO.NC1=NNC=C1C(=O)OCC.FC(C(CC(=O)C1=CC=C(C=C1)C(F)(F)F)=O)F>>FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)F | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][nH:6][n:7][c:25]1[NH2:24].O=[C:8]([CH:9]([F:10])[F:11])[CH2:12][C:13](=O)[c:14]1[cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][cH:23]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6][n:7]2[c:8]([CH:9]([F:10])[F:11])[cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([C:18]([F:19])([F:20])[F:21]... | CCOC(=O)c1c[nH]nc1N.O=C(CC(=O)C(F)F)c1ccc(C(F)(F)F)cc1 | O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | null | null | O.C(C)(=O)O.[OH-].[K+] | Aromatic Heterocycle Formation | OtherReaction | 844b7d6c384974fa5ba69b18a39b58040d6152396b7d27683072d38f7bb168e3 | 9f5d022888af748ddf691538636b27f504746b4da4029f970856433120ab8252 | c1ccc(-c2ccn3nccc3n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[nH;D2;+0:6]:[n;H0;D2;+0:7]:[c:8]:1-[NH2;D1;+0:9].O=[C;H0;D3;+0:10](-[CH2;D2;+0:11]-[C;H0;D3;+0:12](=O)-[C:13](-[F;D1;H0:14])-[F;D1;H0:15])-[c;H0;D3;+0:16](:[c:17]:[c:18]):[c:19]:[c:20]>>[F;D1;H0:14]-[C:13](-[F;D1;H0:15])-[c;H0;D3;+0:12]1:[cH;D2;+0:11]:[c;H0;D3;+0:10]... | 57.4 | [{"value": 57.0, "product": "FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 57.4, "product": "FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 1.5 | HOUR | A stirred mixture of commercially available 3-amino-4-ethoxycarbonyl-pyrazole (3.38 g, 22 mmol) and 4,4-difluoro-1-(4-trifluoromethyl-phenyl)-butane-1,3-dione (5.8 g, 22 mmol) in acetic acid (45 ml) was heated under reflux conditions for 1.5 h. The reaction mixture was evaporated and the crude product (yellow solid, 8.... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Ester.Primary amine | Carboxylic acid | c1cn[nH]c1 | c1cnc2ccnn2c1 | c1cnc2ccnn2c1.c1ccccc1 | HO- | O.C(C)(=O)O.[OH-].[K+] | 60 | 1.5 | CCOC(=O)c1c[nH]nc1N.O=C(CC(=O)C(F)F)c1ccc(C(F)(F)F)cc1>O.C(C)(=O)O.[OH-].[K+]>O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-878edb3fdef54ad1b4252270da52ffab | CCOC(=O)CC(=O)c1ccc(Cl)cc1.CCOC(=O)c1cn[nH]c1N>>CCOC(=O)c1cnn2c(O)cc(-c3ccc(Cl)cc3)nc12 | ClC1=CC=C(C=C1)C(CC(=O)OCC)=O.NC1=C(C=NN1)C(=O)OCC.C(C)(=O)OCC>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)O)N=CC2C(=O)OCC | CCO[C:10](=[O:11])[CH2:12][C:13](=O)[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][nH:9][c:22]1[NH2:21]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][n:9]2[c:10]([OH:11])[cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]3)[n:21][c:22]12 | CCOC(=O)CC(=O)c1ccc(Cl)cc1.CCOC(=O)c1cn[nH]c1N | CCOC(=O)c1cnn2c(O)cc(-c3ccc(Cl)cc3)nc12 | null | null | CCCCCC | Aromatic Heterocycle Formation | OtherReaction | cf1b86977098d79b7be1ece6873bda7f30c6d01911ab0f65ca6847b1b18f1972 | e4cbab44abd9117eb42f959793b157d31b1dce9de3f9c3954c67bf975e572e43 | c1ccc(-c2ccn3nccc3n2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[#8:10]-[C:11](=[O;D1;H0:12])-[c:13]1:[c:14]:[#7;a:15]:[nH;D2;+0:16]:[c:17]:1-[NH2;D1;+0:18]>>[#8:10]-[C:11](=[O;D1;H0:12])-[c:13]1:[c:14]:[#7;a:15]:[n;H0;D3;+0:16]2:[c:17]:1:[n;H0;D2;+0:18]:[c;H0;D3;+0:4](-[... | 52.3 | [{"value": 52.0, "product": "ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)O)N=CC2C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.3, "product": "ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)O)N=CC2C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 160 | CELSIUS | 3 | HOUR | A mixture of ethyl 3-(4-chloro-phenyl)-3-oxo-propionate (18.1 g, 0.080 mol) and ethyl 5-amino-1H-pyrazole-4-carboxylate (13.7 g, 0.088 mol) was stirred at for 3 h 160° C. Ethyl acetate (40 mL) and hexane (40 mL) were successively added to the cooled mixture and stirring was continued at 0° C. for 0.5 h. The crystals we... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Aromatic alcohol | c1cn[nH]c1 | c1cnc2ccnn2c1 | c1cnc2ccnn2c1.c1ccccc1 | HO- | CCCCCC | 160 | 3 | CCOC(=O)CC(=O)c1ccc(Cl)cc1.CCOC(=O)c1cn[nH]c1N>CCCCCC>CCOC(=O)c1cnn2c(O)cc(-c3ccc(Cl)cc3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3f9e7581880447a5a2ed0b09b5cf30a9 | O=C([O-])c1cnn2c(O)cc(-c3ccc(Cl)cc3)nc12.O=P(Cl)(Cl)Cl>>Clc1ccc(-c2cc(Cl)n3nccc3n2)cc1 | ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)O)N=CC2C(=O)[O-].P(=O)(Cl)(Cl)Cl.CN(C1=CC=CC=C1)C>>ClC1=CC(=NC=2N1N=CC2)C2=CC=C(C=C2)Cl | O=C([O-])[c:13]1[cH:12][n:11][n:10]2[c:8](O)[cH:7][c:6](-[c:5]3[cH:4][cH:3][c:2]([Cl:1])[cH:17][cH:16]3)[n:15][c:14]21.O=P(Cl)(Cl)[Cl:9]>>[Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([Cl:9])[n:10]3[n:11][cH:12][cH:13][c:14]3[n:15]2)[cH:16][cH:17]1 | O=C([O-])c1cnn2c(O)cc(-c3ccc(Cl)cc3)nc12.O=P(Cl)(Cl)Cl | Clc1ccc(-c2cc(Cl)n3nccc3n2)cc1 | null | null | null | Functional Group Interconversion | OtherReaction | 30db31a49fb136d312e5cd66a18ec0f0a14dbcb214980b33f05231569e6e02fd | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(-c2ccn3nccc3n2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[c:5]):[#7;a:6]:[c:7]2:[#7;a:8]:1:[#7;a:9]:[c:10]:[c;H0;D3;+0:11]:2-C(=O)-[O-]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4](-[c:5]):[#7;a:6]:[c:7]2:[cH;D2;+0:11]:[c:10]:[#7;a:9]:[#7;a:8]:2:1 | 85.8 | [{"value": 67.0, "product": "ClC1=CC(=NC=2N1N=CC2)C2=CC=C(C=C2)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.8, "product": "ClC1=CC(=NC=2N1N=CC2)C2=CC=C(C=C2)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 2 | HOUR | A mixture of 5-(4-chloro-phenyl)-7-hydroxy-pyrazolo[1,5-a]pyrimidine-3-carboxylate (9.53 g, 0.03 mol), phosphorous oxychloride (11.0 mL, 0.12 mol), and N,N-dimethylaniline (1.3 mL, 0.01 mol) was stirred for 2 h at 100° C. The mixture was evaporated in vacuo and the residue was partitioned between water and dichlorometh... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.c1cnc2ccnn2c1 | Other | null | 100 | 2 | O=C([O-])c1cnn2c(O)cc(-c3ccc(Cl)cc3)nc12.O=P(Cl)(Cl)Cl>>Clc1ccc(-c2cc(Cl)n3nccc3n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-660b23d2f9fb47a0ab3913cfd7c0970a | CCOC(=O)c1cnn2ccc(-c3ccc(Cl)cc3)nc12>>O=C(O)c1cnn2ccc(-c3ccc(Cl)cc3)nc12 | ClC1=CC=C(C=C1)C1=NC=2N(C=C1)N=CC2C(=O)OCC.[OH-].[Na+]>>ClC1=CC=C(C=C1)C1=NC=2N(C=C1)N=CC2C(=O)O | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][n:6][n:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]3)[n:18][c:19]12>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6][n:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]3)[n:18][c:19]12 | CCOC(=O)c1cnn2ccc(-c3ccc(Cl)cc3)nc12 | O=C(O)c1cnn2ccc(-c3ccc(Cl)cc3)nc12 | null | null | O.CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccn3nccc3n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[#7;a:6]:[#7;a:7]:[c:8]:1:[#7;a:9]>>[#7;a:9]:[c:8]1:[#7;a:7]:[#7;a:6]:[c:5]:[c:4]:1-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 100.5 | [{"value": 100.0, "product": "ClC1=CC=C(C=C1)C1=NC=2N(C=C1)N=CC2C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.5, "product": "ClC1=CC=C(C=C1)C1=NC=2N(C=C1)N=CC2C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | A mixture of ethyl 5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylate (0.12 g, 0.4 mmol) and 0.5 N sodium hydroxide solution (4 mL) in methanol (4 mL) was heated to 70° C. for 2 h. The mixture was cooled, diluted with water (8 mL) and concentrated in vacuo. The aqueous solution was acidified to pH 2 by the add... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cnc2ccnn2c1.c1ccccc1 | Other | O.CO | 70 | null | CCOC(=O)c1cnn2ccc(-c3ccc(Cl)cc3)nc12>O.CO>O=C(O)c1cnn2ccc(-c3ccc(Cl)cc3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d04ca5ecb74d49788d7acca3483fc652 | Clc1ccc(-c2cc(Cl)n3nccc3n2)cc1>>CCc1nn2c(CC)cc(-c3ccc(Cl)cc3)nc2c1C(=O)O | ClC1=CC(=NC=2N1N=CC2)C2=CC=C(C=C2)Cl.C(C)[Mg]Cl.C1CCOC1.[Cl-].[NH4+].[Cl-].C(C)[Zn+].C1CCOC1>>C(C)C1=NN2C(N=C(C=C2CC)C2=CC=C(C=C2)Cl)=C1C(=O)O | Cl[c:6]1[n:5]2[n:4][cH:3][cH:20][c:19]2[n:18][c:10](-[c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[cH:9]1>>[CH3:1][CH2:2][c:3]1[n:4][n:5]2[c:6]([CH2:7][CH3:8])[cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]3)[n:18][c:19]2[c:20]1[C:21](=[O:22])[OH:23] | Clc1ccc(-c2cc(Cl)n3nccc3n2)cc1 | CCc1nn2c(CC)cc(-c3ccc(Cl)cc3)nc2c1C(=O)O | null | [Cl-].[Zn+2].[Cl-].C1CCOC1 | C1CCOC1 | Miscellaneous | OtherReaction | 92f787a2564ca3a97e42aad30bf94669330ed751559df294dc5ac03deec7e934 | fa4b80aee7df11396c38706ef5c9907b67e3efceede52703ae298273a9dae2ed | c1ccc(-c2ccn3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6]2:[cH;D2;+0:7]:[cH;D2;+0:8]:[#7;a:9]:[#7;a:10]:2:1>>[C;D1;H3:11]-[C:12]-[c;H0;D3;+0:8]1:[#7;a:9]:[#7;a:10]2:[c:6](:[#7;a:5]:[c:3](-[c:4]):[c:2]:[c;H0;D3;+0:1]:2-[C:13]-[C;D1;H3:14]):[c;H0;D3;+0:7]:1-[C:15](=[O;D1;H0:16])-[O;D1;H1:17] | 54 | [{"value": 54.0, "product": "C(C)C1=NN2C(N=C(C=C2CC)C2=CC=C(C=C2)Cl)=C1C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 7-chloro-5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine (1.0 g, 3.0 mmol), tetrakis(triphenylphosphin)palladium (0.35 g, 0.3 mmol) in THF (5 mL) was added at 20° C. 0.4 M ethylzinc chloride/THF solution (30 mL, 12 mmol; freshly prepared by stirring a mixture of 6 mL of 2 M ethylmagnesium chloride/THF an... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Carboxylic acid | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1cnc2ccnn2c1.c1ccccc1 | null | [Cl-].[Zn+2].[Cl-].C1CCOC1.C1CCOC1 | null | 1 | Clc1ccc(-c2cc(Cl)n3nccc3n2)cc1>[Cl-].[Zn+2].[Cl-].C1CCOC1.C1CCOC1>CCc1nn2c(CC)cc(-c3ccc(Cl)cc3)nc2c1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fb3e16a770474073a55e7d31299261c9 | CC[CH2][Zn+].CCc1cc2nc(-c3ccc(Cl)cc3)cc(Cl)n2n1>>CCCc1cc(-c2ccc(Cl)cc2)nc2c(C(=O)O)cnn12 | C(C)[Mg]Cl.C(C)C1=NN2C(N=C(C=C2Cl)C2=CC=C(C=C2)Cl)=C1.[Cl-].C(C)[Zn+].C1CCOC1.[Cl-].C(CC)[Zn+].C1CCOC1>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)CCC)N=CC2C(=O)O | [Zn+][CH2:3][CH2:2][CH3:1].CC[c:20]1[cH:16][c:15]2[n:14][c:6](-[c:7]3[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]3)[cH:5][c:4](Cl)[n:22]2[n:21]1>>[CH3:1][CH2:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([Cl:11])[cH:12][cH:13]2)[n:14][c:15]2[c:16]([C:17](=[O:18])[OH:19])[cH:20][n:21][n:22]12 | CC[CH2][Zn+].CCc1cc2nc(-c3ccc(Cl)cc3)cc(Cl)n2n1 | CCCc1cc(-c2ccc(Cl)cc2)nc2c(C(=O)O)cnn12 | null | [Cl-].[Zn+2].[Cl-] | null | Acylation | OtherReaction | 144347377e1ef5fa3a9518d33198f48bd9939f652605346b7aedfdfa733cd4bb | fe21bc6a6233cb610624bc05625ea663772d4fed6cd0d46e613d73152e889c6f | c1ccc(-c2ccn3nccc3n2)cc1 | C-C-[c;H0;D3;+0:1]1:[#7;a:2]:[#7;a:3]2:[c:4](:[#7;a:5]:[c:6](-[c:7]):[c:8]:[c;H0;D3;+0:9]:2-Cl):[cH;D2;+0:10]:1.[C;D1;H3:11]-[C:12]-[CH2;D2;+0:13]-[Zn+]>>[C;D1;H3:11]-[C:12]-[CH2;D2;+0:13]-[c;H0;D3;+0:9]1:[c:8]:[c:6](-[c:7]):[#7;a:5]:[c:4]2:[#7;a:3]:1:[#7;a:2]:[cH;D2;+0:1]:[c;H0;D3;+0:10]:2-[C:14](=[O;D1;H0:15])-[O;D1;... | null | [] | null | null | null | null | Subjecting ethyl 7-chloro-5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine in analogous manner to the procedure described in Example C.26, but replacing the ethylzinc chloride/THF solution by a 0.4 M propylzinc chloride/THF solution (freshly prepared from ethylmagnesium chloride and zinc chloride), the title compound was ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Carboxylic acid | c1cnc2ccnn2c1 | c1cnc2ccnn2c1 | c1ccccc1.c1cnc2ccnn2c1 | HCl.Zn | [Cl-].[Zn+2].[Cl-] | null | null | CC[CH2][Zn+].CCc1cc2nc(-c3ccc(Cl)cc3)cc(Cl)n2n1>[Cl-].[Zn+2].[Cl-]>CCCc1cc(-c2ccc(Cl)cc2)nc2c(C(=O)O)cnn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0c69e57e1d774b09bda13c6ca6a21762 | Clc1ccc(-c2cc(Cl)n3nccc3n2)cc1.[Br][Mg][CH]1CC1>>O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(Cl)cc3)nc12 | ClC1=CC(=NC=2N1N=CC2)C2=CC=C(C=C2)Cl.C1(CC1)[Mg]Br.C1CCOC1.[Cl-].[NH4+].[Cl-].C1(CC1)[Zn+].C1CCOC1>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C1CC1)N=CC2C(=O)O | Cl[c:8]1[n:7]2[n:6][cH:5][cH:4][c:22]2[n:21][c:13](-[c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]2)[cH:12]1.[Br][Mg][CH:9]1[CH2:10][CH2:11]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6][n:7]2[c:8]([CH:9]3[CH2:10][CH2:11]3)[cH:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]3)[n:21][c:22]12 | Clc1ccc(-c2cc(Cl)n3nccc3n2)cc1.[Br][Mg][CH]1CC1 | O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(Cl)cc3)nc12 | null | [Cl-].[Zn+2].[Cl-].C1CCOC1 | C1CCOC1 | Acylation | OtherReaction | 2e447f231c85e716e6d1c0a96be9f9fa1bd8bdfba46ffb9416ae8ca5b751b91f | 34e1236212e66341394d532116f64149d7f1159a457f88a51e0a9e0093226265 | c1ccc(-c2cc(C3CC3)n3nccc3n2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c:4]):[#7;a:5]:[c:6]2:[cH;D2;+0:7]:[c:8]:[#7;a:9]:[#7;a:10]:2:1.[Br]-[Mg]-[CH;D3;+0:11]1-[C:12]-[C:13]-1>>[O;D1;H0:14]=[C:15](-[O;D1;H1:16])-[c;H0;D3;+0:7]1:[c:8]:[#7;a:9]:[#7;a:10]2:[c:6]:1:[#7;a:5]:[c:3](-[c:4]):[c:2]:[c;H0;D3;+0:1]:2-[CH;D3;+0:11]1-[C:12]-[C:13]-1 | null | [] | null | null | 1 | HOUR | To a solution of 7-chloro-5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine (4.0 g, 12.0 mmol), tetrakis(triphenylphosphin)palladium (1.15 g, 1.0 mmol) in THF (20 mL) was added at 20° C. 0.25 M cyclopropylzinc chloride/THF suspension (ca.192 mL, 48 mol; freshly prepared by stirring a mixture of 96 mL of 0.5 M cyclopropylma... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aromatic halide | Carboxylic acid | c1cnc2ccnn2c1.C1CC1 | C1CC1.c1cnc2ccnn2c1 | C1CC1.c1cnc2ccnn2c1.c1ccccc1 | null | [Cl-].[Zn+2].[Cl-].C1CCOC1.C1CCOC1 | null | 1 | Clc1ccc(-c2cc(Cl)n3nccc3n2)cc1.[Br][Mg][CH]1CC1>[Cl-].[Zn+2].[Cl-].C1CCOC1.C1CCOC1>O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(Cl)cc3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-178194fa6457412ba9806a2696665be3 | CCO.NC(=O)c1nc[nH]c1N>>CCOC(=O)c1nc[nH]c1N | NC1=C(N=CN1)C(=O)N.C(C)O>>C(C)OC(=O)C=1N=CNC1N | [CH3:1][CH2:2][OH:3].N[C:4](=[O:5])[c:6]1[n:7][cH:8][nH:9][c:10]1[NH2:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][nH:9][c:10]1[NH2:11] | CCO.NC(=O)c1nc[nH]c1N | CCOC(=O)c1nc[nH]c1N | null | null | CS(=O)(=O)O | Acylation | OtherReaction | f7d282027fef43aeffb6ee6f9e0efa97d1de0371e40c2d4f8cdc8dae72a20151 | 37e3ebff23539286094626c8305de24c7fe1b30501da18ae28d82eb98e5260c0 | c1c[nH]cn1 | N-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[N;D1;H2:8].[C;D1;H3:9]-[C:10]-[OH;D1;+0:11]>>[C;D1;H3:9]-[C:10]-[O;H0;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:1-[N;D1;H2:8] | 45 | [{"value": 45.0, "product": "C(C)OC(=O)C=1N=CNC1N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A stirred solution of commercially available 5-amino-1H-imidazole-4-carboxamide (25 g, 198 mmol) in methanesulfonic acid (107 ml) and ethanol (400 ml) was stirred at reflux conditions for 12d, evaporated and water (300 ml) was added. While stirring and cooling (ice/water) sodium hydroxide solution (32%) was added until... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide.Primary alcohol | Ester | null | null | c1c[nH]cn1 | Other | CS(=O)(=O)O | null | null | CCO.NC(=O)c1nc[nH]c1N>CS(=O)(=O)O>CCOC(=O)c1nc[nH]c1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4bc654c8437849e4accef59d726bad3f | CCOC(=O)c1nc[nH]c1N.O=C(CC(=O)C(F)(F)F)c1ccc(C(F)(F)F)cc1>>CCOC(=O)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | FC(C(CC(=O)C1=CC=C(C=C1)C(F)(F)F)=O)(F)F.C(C)OC(=O)C=1N=CNC1N>>C(C)OC(=O)C=1N=CN2C1N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][nH:9][c:28]1[NH2:27].O=[C:10]([C:11]([F:12])([F:13])[F:14])[CH2:15][C:16](=O)[c:17]1[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][n:9]2[c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][c:16](-[c:17]3[cH:18... | CCOC(=O)c1nc[nH]c1N.O=C(CC(=O)C(F)(F)F)c1ccc(C(F)(F)F)cc1 | CCOC(=O)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | ce8dbf17366e85d00a8cf1d06862b8747151f7f8c00680cbd70c0ef68fd03297 | e8142154ce82c2e242e52c937b939f3fefdc51b29f1e30581e6f69472c9bf693 | c1ccc(-c2ccn3cncc3n2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])-[C:9](-[F;D1;H0:10])(-[F;D1;H0:11])-[F;D1;H0:12].[#8:13]-[C:14](=[O;D1;H0:15])-[c:16]1:[#7;a:17]:[c:18]:[nH;D2;+0:19]:[c:20]:1-[NH2;D1;+0:21]>>[#8:13]-[C:14](=[O;D1;H0:15])-[c:16]1:[#7;a:17]:[c:18]:[n;H0;D3;+0:19]2:[c:20]:1:[n;... | 43.5 | [{"value": 43.0, "product": "C(C)OC(=O)C=1N=CN2C1N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.5, "product": "C(C)OC(=O)C=1N=CN2C1N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4,4,4-trifluoro-1-(4-trifluoromethyl-phenyl)-butane-1,3-dione (10.0 g, 35.2 mmol) and 5-amino-1H-imidazole-4-carboxylic acid ethyl ester (5.0 g, 32.2 mmol) in acetic acid (120 ml) was refluxed for 24 h and evaporated. The crude product was further purified by column chromatography on silica gel (ethyl acet... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone.Primary amine | null | c1c[nH]cn1 | c1cnc2cncn2c1 | c1cnc2cncn2c1.c1ccccc1 | HO- | C(C)(=O)O | null | null | CCOC(=O)c1nc[nH]c1N.O=C(CC(=O)C(F)(F)F)c1ccc(C(F)(F)F)cc1>C(C)(=O)O>CCOC(=O)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb2753a79918404f93554e287a063795 | CCOC(=O)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>O=C(O)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | C(C)OC(=O)C=1N=CN2C1N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F.[OH-].[K+].O>>FC(C1=CC(=NC=2N1C=NC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)(F)F | CC[O:3][C:2](=[O:1])[c:4]1[n:5][cH:6][n:7]2[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]3)[n:25][c:26]12>>[O:1]=[C:2]([OH:3])[c:4]1[n:5][cH:6][n:7]2[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([C:19]([F:20])([F:21... | CCOC(=O)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | O=C(O)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | null | null | C(C)(=O)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccn3cncc3n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[c:6](:[#7;a:7]):[#7;a:8]>>[#7;a:7]:[c:6](:[#7;a:8]):[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[#7;a:5] | 37 | [{"value": 37.0, "product": "FC(C1=CC(=NC=2N1C=NC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.0, "product": "FC(C1=CC(=NC=2N1C=NC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | A mixture of 4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid ethyl ester (5.6 g, 13.9 mmol), 2M potassium hydroxide solution (111 ml) and water (55 ml) was stirred at room temperature for 5 h, cooled (ice-water), and acetic acid (30 ml) was added. The mixture was evaporated, ac... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cnc2cncn2c1.c1ccccc1 | Other | C(C)(=O)O | null | 5 | CCOC(=O)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>C(C)(=O)O>O=C(O)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8dc84b303dea4be3bbc47a0339a56ff2 | COc1ccc(CN)cc1.FC(F)(F)c1cccnc1Cl>>COc1ccc(CNc2ncccc2C(F)(F)F)cc1 | ClC1=NC=CC=C1C(F)(F)F.COC1=CC=C(CN)C=C1.CCN(C(C)C)C(C)C>>COC1=CC=C(CNC2=NC=CC=C2C(F)(F)F)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH2:8])[cH:19][cH:20]1.Cl[c:9]1[n:10][cH:11][cH:12][cH:13][c:14]1[C:15]([F:16])([F:17])[F:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[n:10][cH:11][cH:12][cH:13][c:14]2[C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1 | COc1ccc(CN)cc1.FC(F)(F)c1cccnc1Cl | COc1ccc(CNc2ncccc2C(F)(F)F)cc1 | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2ccccn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[C:5](-[F;D1;H0:6])(-[F;D1;H0:7])-[F;D1;H0:8]):[c:9].[NH2;D1;+0:10]-[C:11]-[c:12]>>[F;D1;H0:6]-[C:5](-[F;D1;H0:7])(-[F;D1;H0:8])-[c:4](:[c:9]):[c;H0;D3;+0:1](-[NH;D2;+0:10]-[C:11]-[c:12]):[#7;a:2]:[c:3] | 83.1 | [{"value": 83.0, "product": "COC1=CC=C(CNC2=NC=CC=C2C(F)(F)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.1, "product": "COC1=CC=C(CNC2=NC=CC=C2C(F)(F)F)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | A mixture of 2-chloro-3-trifluoromethylpyridine (64.83 g, 357 mmol), 4-methoxybenzylamine (56 mL, 429 mmol) and DIPEA (73.4 mL, 429 mmol) in n-butanol (100 mL) was refluxed (oil bath temp. 140° C.) for 3.5 days. Concentrated in vacuum, partitioned between 25% HCl and TBME, reextracted the organic layer twice with 25% H... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | HCl | C(CCC)O | 140 | null | COc1ccc(CN)cc1.FC(F)(F)c1cccnc1Cl>C(CCC)O>COc1ccc(CNc2ncccc2C(F)(F)F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-765380b3b4fe41aa9f44176e13803bc8 | CC#N.Nc1ncccc1C(F)(F)F.O=C1CCC(=O)N1Br>>O=C(O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12 | C(=O)(O)[O-].[Na+].FC(C=1C(=NC=CC1)N)(F)F.C1CC(=O)N(C1=O)Br.C(C)#N>>FC(C=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C(=O)O)(F)F | N#[C:24][CH3:23].[NH2:6][c:7]1[c:8]([C:9]([F:10])([F:12])[F:20])[cH:13][cH:14][cH:25][n:26]1.O=[C:18]1N(Br)[C:2](=[O:1])[CH2:4][CH2:5]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6][c:7]2[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]3)[cH:25][n:26]12 | CC#N.Nc1ncccc1C(F)(F)F.O=C1CCC(=O)N1Br | O=C(O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | a93581ca936433fbb116d38436efcf9f554ba45359aec0b6ca55aeb3e6646d78 | 1cf91e57ab9c59b29afc31e5cb032482b08ae13d9d439874b7c8ff03778eae48 | c1ccc(-c2ccc3nccn3c2)cc1 | Br-N1-[C;H0;D3;+0:1](=O)-[CH2;D2;+0:2]-[CH2;D2;+0:3]-[C;H0;D3;+0:4]-1=[O;D1;H0:5].N#[C;H0;D2;+0:6]-[CH3;D1;+0:7].[F;D1;H0:8]-[C;H0;D4;+0:9](-[F;D1;H0:10])(-[F;H0;D1;+0:11])-[c:12]1:[c:13]:[cH;D2;+0:14]:[c:15]:[n;H0;D2;+0:16]:[c:17]:1-[NH2;D1;+0:18]>>[F;D1;H0:8]-[C;H0;D4;+0:9](-[F;D1;H0:19])(-[F;D1;H0:10])-[c:12]1:[c:13... | 98 | [{"value": 98.0, "product": "FC(C=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C(=O)O)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | 23 | CELSIUS | 1 | HOUR | To a solution of the above 3-trifluoromethyl-pyridin-2-ylamine (16.21 g, 100 mmol) in acetonitrile (300 mL) at 5° C. was added NBS (17.8 g, 100 mmol) and the mixture was stirred at 23° C. for 1 h. Poured into ice and additional sat. NaHCO3-sol., extracted with EtOAc, washed with brine, dried over Na2SO4. Removal of the... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Nitrile.Tertiary amide.Tertiary amide.Primary amine | Trifluoro group.Trifluoro group.Carboxylic acid | c1ccncc1.C1CCNC1 | c1ccn2ccnc2c1.c1ccccc1 | c1ccn2ccnc2c1.c1ccccc1 | HBr | null | 23 | 1 | CC#N.Nc1ncccc1C(F)(F)F.O=C1CCC(=O)N1Br>>O=C(O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e6c1d8a0de64ca889d7d2dd02613844 | Nc1ncc(Br)cc1C(F)(F)F.OB(O)c1ccc(C(F)(F)F)cc1>>Nc1ncc(-c2ccc(C(F)(F)F)cc2)cc1C(F)(F)F | C(CC(O)(C(=O)O)CC(=O)O)(=O)O.C(=O)([O-])[O-].[Na+].[Na+].BrC=1C=C(C(=NC1)N)C(F)(F)F.FC(C1=CC=C(C=C1)B(O)O)(F)F>>FC(C=1C(=NC=C(C1)C1=CC=C(C=C1)C(F)(F)F)N)(F)F | Br[c:5]1[cH:4][n:3][c:2]([NH2:1])[c:17]([C:18]([F:19])([F:20])[F:21])[cH:16]1.OB(O)[c:6]1[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1>>[NH2:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][c:17]1[C:18]([F:19])([F:20])[F:21] | Nc1ncc(Br)cc1C(F)(F)F.OB(O)c1ccc(C(F)(F)F)cc1 | Nc1ncc(-c2ccc(C(F)(F)F)cc2)cc1C(F)(F)F | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | COCCOC | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[c:9]:[c:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1):[c:10]:[c:11] | 87 | [{"value": 87.0, "product": "FC(C=1C(=NC=C(C1)C1=CC=C(C=C1)C(F)(F)F)N)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of the above 5-bromo-3-trifluoromethyl-pyridin-2-ylamine (9.90 g, 41.1 mmol), commercially available 4-(trifluoromethyl)benzeneboronic acid CAS-No. [128796-39-4] (8.58 g, 45.2 mmol), 1N aqueous Na2CO3-solution (98.6 mL, 98.6 mmol) and Pd(PPh3)4 (475 mg, 1 mol %) in DME (205 mL) was refluxed under argon atmosp... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC | null | null | Nc1ncc(Br)cc1C(F)(F)F.OB(O)c1ccc(C(F)(F)F)cc1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.COCCOC>Nc1ncc(-c2ccc(C(F)(F)F)cc2)cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e2e423795214afcbdaa5cff9a56d464 | COC(OC)N(C)C.Nc1ncc(-c2ccc(C(F)(F)F)cc2)cc1C(F)(F)F>>CN(C)C=Nc1ncc(-c2ccc(C(F)(F)F)cc2)cc1C(F)(F)F | FC(C=1C(=NC=C(C1)C1=CC=C(C=C1)C(F)(F)F)N)(F)F.COC(N(C)C)OC>>CN(C=NC1=NC=C(C=C1C(F)(F)F)C1=CC=C(C=C1)C(F)(F)F)C | CO[CH:4](OC)[N:2]([CH3:1])[CH3:3].[NH2:5][c:6]1[n:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]2)[cH:20][c:21]1[C:22]([F:23])([F:24])[F:25]>>[CH3:1][N:2]([CH3:3])[CH:4]=[N:5][c:6]1[n:7][cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]2)[cH:20][... | COC(OC)N(C)C.Nc1ncc(-c2ccc(C(F)(F)F)cc2)cc1C(F)(F)F | CN(C)C=Nc1ncc(-c2ccc(C(F)(F)F)cc2)cc1C(F)(F)F | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | 0d701f00585e4f39a6a7fc9a495a6e4c12bb39eb0ddc06ef90888eddc323e4b7 | e5ad6b21478dc075562b413728aa025da8232f58653a7afd9501cb514659723b | c1ccc(-c2cccnc2)cc1 | C-O-[CH;D3;+0:1](-O-C)-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[C;D1;H3:3]-[#7:2](-[C;D1;H3:4])-[CH;D2;+0:1]=[N;H0;D2;+0:5]-[c:6](:[c:7]):[#7;a:8]:[c:9] | 78 | [{"value": 78.0, "product": "CN(C=NC1=NC=C(C=C1C(F)(F)F)C1=CC=C(C=C1)C(F)(F)F)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.7, "product": "CN(C=NC1=NC=C(C=C1C(F)(F)F)C1=CC=C(C=C1)C(F)(F)F)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of the above 3-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyridin-2-ylamine (4.59 g, 15 mmol) and dimethylformamide dimethyl acetal (2.25 mL, 16 mmol) in toluene was refluxed for 1 h. The reaction mixture was evaporated and dried at HV to give the title compound as a light yellow solid (4.21 g, 78%). MS (IS... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amine | null | null | null | c1ccncc1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | COC(OC)N(C)C.Nc1ncc(-c2ccc(C(F)(F)F)cc2)cc1C(F)(F)F>C1(=CC=CC=C1)C>CN(C)C=Nc1ncc(-c2ccc(C(F)(F)F)cc2)cc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1f6d7f261b74d3bab566f88fcb44317 | CCOC(=O)CBr.CN(C)C=Nc1ncc(-c2ccc(C(F)(F)F)cc2)cc1C(F)(F)F>>CCOC(=O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12 | C(=O)(O)[O-].[Na+].CN(C=NC1=NC=C(C=C1C(F)(F)F)C1=CC=C(C=C1)C(F)(F)F)C.BrCC(=O)OCC.CCN(C(C)C)C(C)C>>C(C)OC(=O)C1=CN=C2N1C=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].CN(C)[CH:7]=[N:8][c:9]1[c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][c:16](-[c:17]2[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]2)[cH:27][n:28]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][n:8][c:9]2[c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][c:16](-[c:17]3[c... | CCOC(=O)CBr.CN(C)C=Nc1ncc(-c2ccc(C(F)(F)F)cc2)cc1C(F)(F)F | CCOC(=O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | db764b17e755b498fd14eb5f9072e6c8267cc58965602bf097d0758962f4f7ff | 1ce2910797fab93ee9b2514455c0e4b3d1e921f9723bc4f43d9e00c74f577a58 | c1ccc(-c2ccc3nccn3c2)cc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].C-N(-C)-[CH;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[n;H0;D2;+0:10]:[c:11]:[c:12]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[c;H0;D3;+0:1]1:[cH;D2;+0:6]:[n;H0;D2;+0:7]:[c:8](:[c:9]):[n;H0;D3;+0:10]:1:[c:11]:[c:12] | 72 | [{"value": 72.0, "product": "C(C)OC(=O)C1=CN=C2N1C=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.8, "product": "C(C)OC(=O)C1=CN=C2N1C=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 4 | HOUR | A mixture of the above N,N-dimethyl-N′-[3-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-formamidine (3.61 g, 10.0 mmol) and ethyl bromoacetate (3.32 mL, 30.0 mmol) in DMF (10 mL) was stirred at 120° C. for 4 h. Cooled down to 100° C., added DIPEA (0.5 mL, 3.0 mmol) and stirred at 23° C. for 2 h. Poured int... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Tertiary amine | Ester | c1ccncc1 | c1ccn2ccnc2c1 | c1ccn2ccnc2c1.c1ccccc1 | HBr | CN(C)C=O | 120 | 4 | CCOC(=O)CBr.CN(C)C=Nc1ncc(-c2ccc(C(F)(F)F)cc2)cc1C(F)(F)F>CN(C)C=O>CCOC(=O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-474b2de1ed724182b0c59b6204071766 | CCOC(=O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12>>O=C(O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12 | [Na+].[Cl-].C(C)OC(=O)C1=CN=C2N1C=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F.O[Li].O.Cl>>FC(C=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C(=O)O)(F)F | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][n:6][c:7]2[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][cH:24]3)[cH:25][n:26]12>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6][c:7]2[c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([C:19]([F:20])([F:2... | CCOC(=O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12 | O=C(O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12 | null | null | O.CO.C1CCOC1 | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2ccc3nccn3c2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[c:6]:[#7;a:7]>>[#7;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[c:6]:[#7;a:7] | null | [] | 23 | CELSIUS | 3 | HOUR | To a solution of the above 8-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid ethyl ester (3.06 g, 7.61 mmol) in THF (45 mL), MeOH (5 mL) and water (11.3 mL) at 23° C. was added LiOH·H2O (479 mg, 11.41 mmol) and the mixture was stirred at 23° C. for 3 h. Poured into icewater, adjust... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccn2ccnc2c1.c1ccccc1 | Other | O.CO.C1CCOC1 | 23 | 3 | CCOC(=O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12>O.CO.C1CCOC1>O=C(O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-429cd21d66e24421b8ef5a17a770dcba | Cc1cc(Br)cnc1N.OB(O)c1ccc(Cl)cc1>>Cc1cc(-c2ccc(Cl)cc2)cnc1N | NC1=NC=C(C=C1C)Br.ClC1=CC=C(C=C1)B(O)O>>ClC1=CC=C(C=C1)C=1C=C(C(=NC1)N)C | Br[c:4]1[cH:3][c:2]([CH3:1])[c:14]([NH2:15])[n:13][cH:12]1.OB(O)[c:5]1[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]1>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[cH:12][n:13][c:14]1[NH2:15] | Cc1cc(Br)cnc1N.OB(O)c1ccc(Cl)cc1 | Cc1cc(-c2ccc(Cl)cc2)cnc1N | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[c:9]:[c:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1):[c:10]:[c:11] | 83 | [{"value": 83.0, "product": "ClC1=CC=C(C=C1)C=1C=C(C(=NC1)N)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.5, "product": "ClC1=CC=C(C=C1)C=1C=C(C(=NC1)N)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared as described in example C.32 (step 4) from commercially available 2-amino-5-bromo-3-methyl-pyridine (4 g, 21.4 mmol) and commercially available 4-chlorophenylboronic acid (3.68 g, 23.5 mmol). Obtained as an off-white solid (3.86 g, 83%). MS (EI) 218.1 [(M)+]; mp 156° C.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HBr.B | null | null | null | Cc1cc(Br)cnc1N.OB(O)c1ccc(Cl)cc1>>Cc1cc(-c2ccc(Cl)cc2)cnc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1199af4504b547a281d8fc4822f31bea | Cc1cc(Br)cnc1N.OB(O)c1ccc(C(F)(F)F)cc1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)cnc1N | NC1=NC=C(C=C1C)Br.FC(C1=CC=C(C=C1)B(O)O)(F)F>>CC=1C(=NC=C(C1)C1=CC=C(C=C1)C(F)(F)F)N | Br[c:4]1[cH:3][c:2]([CH3:1])[c:17]([NH2:18])[n:16][cH:15]1.OB(O)[c:5]1[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]1>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]2)[cH:15][n:16][c:17]1[NH2:18] | Cc1cc(Br)cnc1N.OB(O)c1ccc(C(F)(F)F)cc1 | Cc1cc(-c2ccc(C(F)(F)F)cc2)cnc1N | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[c:9]:[c:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1):[c:10]:[c:11] | 88.2 | [{"value": 88.0, "product": "CC=1C(=NC=C(C1)C1=CC=C(C=C1)C(F)(F)F)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.2, "product": "CC=1C(=NC=C(C1)C1=CC=C(C=C1)C(F)(F)F)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared as described in example C.32 (step 4) from commercially available 2-amino-5-bromo-3-methyl-pyridine (4.5 g, 24.1 mmol) and commercially available 4-trifluoromethyl-phenylboronic acid (5.03 g, 26.5 mmol). Obtained as an off-white solid (5.36 g, 88%). MS (ISP) 252.9 [(M+H)+]; mp 159° C.
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HBr.B | null | null | null | Cc1cc(Br)cnc1N.OB(O)c1ccc(C(F)(F)F)cc1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)cnc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-785a487c5fbf4bb5aa1178801ab47bc1 | Nc1ccc(Br)cn1.OB(O)c1ccc(C(F)(F)F)cc1>>Nc1ccc(-c2ccc(C(F)(F)F)cc2)cn1 | NC1=NC=C(C=C1)Br.FC(C1=CC=C(C=C1)B(O)O)(F)F>>FC(C1=CC=C(C=C1)C=1C=CC(=NC1)N)(F)F | Br[c:5]1[cH:4][cH:3][c:2]([NH2:1])[n:17][cH:16]1.OB(O)[c:6]1[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15]2)[cH:16][n:17]1 | Nc1ccc(Br)cn1.OB(O)c1ccc(C(F)(F)F)cc1 | Nc1ccc(-c2ccc(C(F)(F)F)cc2)cn1 | null | null | null | C-C Coupling | Suzuki coupling with boronic acids | 07e9b6e71d806aa92d4573f3838e77c7c8344de3e5d5735ebdb5fc6862ebf27d | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | c1ccc(-c2cccnc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.O-B(-O)-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[c:9]:[c:8]:[c;H0;D3;+0:7](-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1):[c:10]:[c:11] | 71 | [{"value": 71.0, "product": "FC(C1=CC=C(C=C1)C=1C=CC(=NC1)N)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.5, "product": "FC(C1=CC=C(C=C1)C=1C=CC(=NC1)N)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared as described in example C.32 (step 4) from commercially available 2-amino-5-bromo-pyridine (3.46 g, 20.0 mmol) and commercially available 4-trifluoromethyl-phenylboronic acid (4.18 g, 22.0 mmol). Obtained as an off-white solid (3.36 g, 71%). Mp 130° C.
Conditions: See reaction.notes.procedure_details.
Workup: ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | c1ccncc1.c1ccccc1 | HBr.B | null | null | null | Nc1ccc(Br)cn1.OB(O)c1ccc(C(F)(F)F)cc1>>Nc1ccc(-c2ccc(C(F)(F)F)cc2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-090d8dd1a3d046c8baa561799281f316 | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cc1 | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)(F)F.ONC(C1=CC=C(C=C1)S(N)(=O)=O)=N>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C2=CC=C(C=C2)S(=O)(=O)N)C2=CC=C(C=C2)C(F)(F)F)(F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:36])[cH:37][cH:38]1.O=[C:12](O)[c:13]1[cH:14][n:15][n:16]2[c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][c:23](-[c:24]3[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]3)[n:34][c:35]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:... | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14](:[c:15]:[... | null | [] | null | null | null | null | The title compound was prepared from 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.2) (188 mg, 0.5 mmol) and N-hydroxy-4-sulfamoyl-benzamidine [CAS-No. 4476-10-2] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromatog... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d992d614470b43449d5b997f62f0c0bb | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)c1 | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)(F)F.ONC(C1=CC(=CC=C1)S(N)(=O)=O)=N>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C=2C=C(C=CC2)S(=O)(=O)N)C2=CC=C(C=C2)C(F)(F)F)(F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([NH:11][OH:12])=[NH:37])[cH:38]1.O=[C:13](O)[c:14]1[cH:15][n:16][n:17]2[c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][c:24](-[c:25]3[cH:26][cH:27][c:28]([C:29]([F:30])([F:31])[F:32])[cH:33][cH:34]3)[n:35][c:36]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:... | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14](:[c:15]:[... | null | [] | null | null | null | null | The title compound was prepared from 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.2) (188 mg, 0.5 mmol) and N-hydroxy-3-sulfamoyl-benzamidine [CAS-No. 9000-88-7] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromato... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ba218c3467ee4366a1ad32eea9619761 | N=C(NO)c1cccnc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>FC(F)(F)c1ccc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)(F)F.ONC(C1=CN=CC=C1)=N>>N1=CC(=CC=C1)C1=NOC(=N1)C=1C=NN2C1N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F | [NH:21]=[C:22]([c:23]1[cH:24][cH:25][cH:26][n:27][cH:28]1)[NH:29][OH:30].O=[C:20](O)[c:19]1[cH:18][n:17][n:16]2[c:11]([C:12]([F:13])([F:14])[F:15])[cH:10][c:9](-[c:8]3[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:34][cH:33]3)[n:32][c:31]21>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][c:11]([C:12]([F... | N=C(NO)c1cccnc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | FC(F)(F)c1ccc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[c:16]:[c:17]:[#7;a:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14... | null | [] | null | null | null | null | The title compound was prepared from 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.2) (188 mg, 0.5 mmol) and commercially available N-hydroxy-nicotinamidine [CAS-No. 1594-58-7] (103 mg, 0.75 mmol) according to general procedure II. Obtained after purification by c... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1cnc2ccnn2c1.c1ncon1.c1ccncc1 | HO- | null | null | null | N=C(NO)c1cccnc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>FC(F)(F)c1ccc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-63256512fbcb4bf09eb2bfdd08c69f29 | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cc1 | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)F.ONC(C1=CC=C(C=C1)S(N)(=O)=O)=N>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C2=CC=C(C=C2)S(=O)(=O)N)C2=CC=C(C=C2)C(F)(F)F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:35])[cH:36][cH:37]1.O=[C:12](O)[c:13]1[cH:14][n:15][n:16]2[c:17]([CH:18]([F:19])[F:20])[cH:21][c:22](-[c:23]3[cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31][cH:32]3)[n:33][c:34]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]... | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14](:[c:15]:[... | null | [] | null | null | null | null | The title compound was prepared from 7-difluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.1) (179 mg, 0.5 mmol) and N-hydroxy-4-sulfamoyl-benzamidine [CAS-No. 4476-10-2] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromatog... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-68e2e13495354ba1abaa3f65d4008f5f | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)c1 | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)F.ONC(C1=CC(=CC=C1)S(N)(=O)=O)=N>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C=2C=C(C=CC2)S(=O)(=O)N)C2=CC=C(C=C2)C(F)(F)F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([NH:11][OH:12])=[NH:36])[cH:37]1.O=[C:13](O)[c:14]1[cH:15][n:16][n:17]2[c:18]([CH:19]([F:20])[F:21])[cH:22][c:23](-[c:24]3[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]3)[n:34][c:35]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8... | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14](:[c:15]:[... | null | [] | null | null | null | null | The title compound was prepared from 7-difluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.1) (179 mg, 0.5 mmol) and N-hydroxy-3-sulfamoyl-benzamidine [CAS-No. 9000-88-7] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromatog... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-156506c18ef64190a74f64c5ed7f4b64 | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(Cl)cc5)nc34)n2)c1 | ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C1CC1)N=CC2C(=O)O.ONC(C1=CC(=CC=C1)S(N)(=O)=O)=N>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C1CC1)N=CC2C2=NC(=NO2)C=2C=C(C=CC2)S(=O)(=O)N | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([NH:11][OH:12])=[NH:33])[cH:34]1.O=[C:13](O)[c:14]1[cH:15][n:16][n:17]2[c:18]([CH:19]3[CH2:20][CH2:21]3)[cH:22][c:23](-[c:24]3[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]3)[n:31][c:32]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9](-[c:10]2[n... | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(Cl)cc3)nc12 | NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(Cl)cc5)nc34)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2cc(C3CC3)n3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14](:[c:15]:[... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.28) (157 mg, 0.5 mmol) and N-hydroxy-3-sulfamoyl-benzamidine [CAS-No. 9000-88-7] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromatography (dich... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.C1CC1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(Cl)cc5)nc34)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a166a762556846cd9ef1e750b9eb0717 | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)c1 | C1(CC1)C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F.ONC(C1=CC(=CC=C1)S(N)(=O)=O)=N>>C1(CC1)C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C=2C=C(C=CC2)S(=O)(=O)N)C2=CC=C(C=C2)C(F)(F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([NH:11][OH:12])=[NH:36])[cH:37]1.O=[C:13](O)[c:14]1[cH:15][n:16][n:17]2[c:18]([CH:19]3[CH2:20][CH2:21]3)[cH:22][c:23](-[c:24]3[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]3)[n:34][c:35]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][... | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(C(F)(F)F)cc3)nc12 | NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2cc(C3CC3)n3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14](:[c:15]:[... | null | [] | null | null | null | null | The title compound was prepared from 7-cyclopropyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.29) (174 mg, 0.5 mmol) and N-hydroxy-3-sulfamoyl-benzamidine [CAS-No. 9000-88-7] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromatogra... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.C1CC1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-be8ac4c76d034cb7a3fb5fa34b045e96 | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(Cl)cc5)nc34)n2)cc1 | ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C1CC1)N=CC2C(=O)O.ONC(C1=CC=C(C=C1)S(N)(=O)=O)=N>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C1CC1)N=CC2C2=NC(=NO2)C2=CC=C(C=C2)S(=O)(=O)N | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:32])[cH:33][cH:34]1.O=[C:12](O)[c:13]1[cH:14][n:15][n:16]2[c:17]([CH:18]3[CH2:19][CH2:20]3)[cH:21][c:22](-[c:23]3[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]3)[n:30][c:31]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][o:... | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(Cl)cc3)nc12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(Cl)cc5)nc34)n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2cc(C3CC3)n3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14](:[c:15]:[... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.28) (157 mg, 0.5 mmol) and N-hydroxy-4-sulfamoyl-benzamidine [CAS-No. 4476-10-2] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromatography (dich... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.C1CC1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(Cl)cc5)nc34)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe6faf6f2c544e50a1ad7df471d0cc52 | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cc1 | C1(CC1)C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F.ONC(C1=CC=C(C=C1)S(N)(=O)=O)=N>>C1(CC1)C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C2=CC=C(C=C2)S(=O)(=O)N)C2=CC=C(C=C2)C(F)(F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:35])[cH:36][cH:37]1.O=[C:12](O)[c:13]1[cH:14][n:15][n:16]2[c:17]([CH:18]3[CH2:19][CH2:20]3)[cH:21][c:22](-[c:23]3[cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31][cH:32]3)[n:33][c:34]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][... | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(C(F)(F)F)cc3)nc12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2cc(C3CC3)n3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14](:[c:15]:[... | null | [] | null | null | null | null | The title compound was prepared from 7-cyclopropyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.29) (174 mg, 0.5 mmol) and N-hydroxy-4-sulfamoyl-benzamidine [CAS-No. 4476-10-2] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromatogra... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.C1CC1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a4a0ddef59f748d7a8e6ef6c260d9afe | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)c1 | ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.ONC(C1=CC(=CC=C1)S(N)(=O)=O)=N>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C=2C=C(C=CC2)S(=O)(=O)N | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([NH:11][OH:12])=[NH:34])[cH:35]1.O=[C:13](O)[c:14]1[cH:15][n:16][n:17]2[c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][c:24](-[c:25]3[cH:26][cH:27][c:28]([Cl:29])[cH:30][cH:31]3)[n:32][c:33]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9](-[c:10]... | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12 | NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14](:[c:15]:[... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.4) (171 mg, 0.5 mmol) and N-hydroxy-3-sulfamoyl-benzamidine [CAS-No. 9000-88-7] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromatography (d... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8223c39eaae844cfa4a781e8201f5051 | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnc4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)cn34)n2)c1 | FC(C=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C(=O)O)(F)F.ONC(C1=CC(=CC=C1)S(N)(=O)=O)=N>>FC(C=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C2=NC(=NO2)C=2C=C(C=CC2)S(=O)(=O)N)(F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([NH:11][OH:12])=[NH:37])[cH:38]1.O=[C:13](O)[c:14]1[cH:15][n:16][c:17]2[c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][c:24](-[c:25]3[cH:26][cH:27][c:28]([C:29]([F:30])([F:31])[F:32])[cH:33][cH:34]3)[cH:35][n:36]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH... | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12 | NS(=O)(=O)c1cccc(-c2noc(-c3cnc4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)cn34)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5ccccc5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5](:[c:6]):[#7;a:7]:1:[c:8].[NH;D1;+0:9]=[C;H0;D3;+0:10](-[NH;D2;+0:11]-[OH;D1;+0:12])-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:9]:[c;H0;D3;+0:10](-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:... | null | [] | null | null | null | null | The title compound was prepared from 8-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.32) (187 mg, 0.5 mmol) and N-hydroxy-3-sulfamoyl-benzamidine [CAS-No. 9000-88-7] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromatogr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1ccn2ccnc2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnc4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)cn34)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-899b5ff86f9344ae95f8c8a8c94f31d5 | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)cc1 | ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.ONC(C1=CC=C(C=C1)S(N)(=O)=O)=N>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C2=CC=C(C=C2)S(=O)(=O)N | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:33])[cH:34][cH:35]1.O=[C:12](O)[c:13]1[cH:14][n:15][n:16]2[c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][c:23](-[c:24]3[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]3)[n:31][c:32]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10]... | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14](:[c:15]:[... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.4) (171 mg, 0.5 mmol) and N-hydroxy-4-sulfamoyl-benzamidine [CAS-No. 4476-10-2] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromatography (et... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dfa5e0927d1442508260b61f5b1937ad | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnc4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)cn34)n2)cc1 | FC(C=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C(=O)O)(F)F.ONC(C1=CC=C(C=C1)S(N)(=O)=O)=N>>FC(C=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C2=NC(=NO2)C2=CC=C(C=C2)S(=O)(=O)N)(F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:36])[cH:37][cH:38]1.O=[C:12](O)[c:13]1[cH:14][n:15][c:16]2[c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][c:23](-[c:24]3[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]3)[cH:34][n:35]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH... | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnc4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)cn34)n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5ccccc5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5](:[c:6]):[#7;a:7]:1:[c:8].[NH;D1;+0:9]=[C;H0;D3;+0:10](-[NH;D2;+0:11]-[OH;D1;+0:12])-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:9]:[c;H0;D3;+0:10](-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:... | null | [] | null | null | null | null | The title compound was prepared from 8-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.32) (187 mg, 0.5 mmol) and N-hydroxy-4-sulfamoyl-benzamidine [CAS-No. 4476-10-2] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromatogra... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1ccn2ccnc2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnc2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)cn12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnc4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)cn34)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ce6f184a0e244812b75a18622c760e91 | N=C(NO)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12.NS(=O)(=O)c1ccc(C(=O)O)cc1>>NS(=O)(=O)c1ccc(-c2nc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)no2)cc1 | ONC(=N)C=1C=NN2C1N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F.S(N)(=O)(=O)C1=CC=C(C(=O)O)C=C1>>FC(C1=CC(=NC=2N1N=CC2C2=NOC(=N2)C2=CC=C(C=C2)S(=O)(=O)N)C2=CC=C(C=C2)C(F)(F)F)(F)F | [NH:10]=[C:11]([c:12]1[cH:13][n:14][n:15]2[c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][c:22](-[c:23]3[cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31][cH:32]3)[n:33][c:34]12)[NH:35][OH:36].O=[C:9](O)[c:8]1[cH:7][cH:6][c:5]([S:2]([NH2:1])(=[O:3])=[O:4])[cH:38][cH:37]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:... | N=C(NO)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12.NS(=O)(=O)c1ccc(C(=O)O)cc1 | NS(=O)(=O)c1ccc(-c2nc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)no2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4noc(-c5ccccc5)n4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH;D1;+0:7]=[C;H0;D3;+0:8](-[NH;D2;+0:9]-[OH;D1;+0:10])-[c;H0;D3;+0:11]1:[c:12]:[#7;a:13]:[#7;a:14](:[c:15]):[c:16]:1:[#7;a:17]:[c:18]>>[c:15]:[#7;a:14]1:[#7;a:13]:[c:12]:[c;H0;D3;+0:11](-[c;H0;D3;+0:8]2:[n;H0;D2;+0:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:... | null | [] | null | null | null | null | The title compound was prepared from N-hydroxy-7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxamidine (example B.1) (195 mg, 0.5 mmol) and commercially available 4-sulfamoyl-benzoic acid (101 mg, 0.5 mmol) according to general procedure II. Obtained after purification by flash chromato... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12.NS(=O)(=O)c1ccc(C(=O)O)cc1>>NS(=O)(=O)c1ccc(-c2nc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)no2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-099429fa0d01480c967c6e0a75904e33 | N=C(NO)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12.NS(=O)(=O)c1cccc(C(=O)O)c1>>NS(=O)(=O)c1cccc(-c2nc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)no2)c1 | ONC(=N)C=1C=NN2C1N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F.S(N)(=O)(=O)C=1C=C(C(=O)O)C=CC1>>FC(C1=CC(=NC=2N1N=CC2C2=NOC(=N2)C=2C=C(C=CC2)S(=O)(=O)N)C2=CC=C(C=C2)C(F)(F)F)(F)F | [NH:11]=[C:12]([c:13]1[cH:14][n:15][n:16]2[c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][c:23](-[c:24]3[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]3)[n:34][c:35]12)[NH:36][OH:37].O=[C:10](O)[c:9]1[cH:8][cH:7][cH:6][c:5]([S:2]([NH2:1])(=[O:3])=[O:4])[cH:38]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:... | N=C(NO)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12.NS(=O)(=O)c1cccc(C(=O)O)c1 | NS(=O)(=O)c1cccc(-c2nc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)no2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4noc(-c5ccccc5)n4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH;D1;+0:7]=[C;H0;D3;+0:8](-[NH;D2;+0:9]-[OH;D1;+0:10])-[c;H0;D3;+0:11]1:[c:12]:[#7;a:13]:[#7;a:14](:[c:15]):[c:16]:1:[#7;a:17]:[c:18]>>[c:15]:[#7;a:14]1:[#7;a:13]:[c:12]:[c;H0;D3;+0:11](-[c;H0;D3;+0:8]2:[n;H0;D2;+0:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:... | null | [] | null | null | null | null | The title compound was prepared from N-hydroxy-7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxamidine (example B.1) (195 mg, 0.5 mmol) and commercially available 3-sulfamoyl-benzoic acid (101 mg, 0.5 mmol) according to general procedure II. Obtained after purification by flash chromato... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12.NS(=O)(=O)c1cccc(C(=O)O)c1>>NS(=O)(=O)c1cccc(-c2nc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)no2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d3f4b785fcbb423d8cb7bc542cbf1a65 | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(OCC(F)(F)F)c3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(OCC(F)(F)F)c5)nc34)n2)c1 | FC(COC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O)(F)F.ONC(C1=CC(=CC=C1)S(N)(=O)=O)=N>>FC(COC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C=2C=C(C=CC2)S(=O)(=O)N)(F)F | O[NH:11][C:10]([c:9]1[cH:8][cH:7][cH:6][c:5]([S:2]([NH2:1])(=[O:3])=[O:4])[cH:44]1)=[NH:43].O=[C:13]([OH:12])[c:14]1[cH:15][n:16][n:17]2[c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][c:24](-[c:25]3[cH:26][cH:27][c:28]([C:29]([F:30])([F:31])[F:32])[c:33]([O:34][CH2:35][C:36]([F:37])([F:38])[F:39])[cH:40]3)[n:41][c:42]12>>[... | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(OCC(F)(F)F)c3)nc12 | NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(OCC(F)(F)F)c5)nc34)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[NH;D2;+0:1]-[C;H0;D3;+0:2](=[NH;D1;+0:3])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].O=[C;H0;D3;+0:9](-[OH;D1;+0:10])-[c;H0;D3;+0:11]1:[c:12]:[#7;a:13]:[#7;a:14](:[c:15]):[c:16]:1:[#7;a:17]:[c:18]>>[c:15]:[#7;a:14]1:[#7;a:13]:[c:12]:[c;H0;D3;+0:11](-[c;H0;D3;+0:9]2:[n;H0;D2;+0:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:4](:[c:5]:... | null | [] | null | null | null | null | The title compound was prepared from 5-[3-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-phenyl]-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.10) (237 mg, 0.5 mmol) and N-hydroxy-3-sulfamoyl-benzamidine [CAS-No. 9000-88-7] (161 mg, 0.75 mmol) according to general procedure II. Obtained after pur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(OCC(F)(F)F)c3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(OCC(F)(F)F)c5)nc34)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9164cd4dd1214f41861e47df9b6366fe | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1cccc(S(N)(=O)=O)c1>>Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5cccc(S(N)(=O)=O)c5)no4)c3n2)ccc1C(F)(F)F | CC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.ONC(C1=CC(=CC=C1)S(N)(=O)=O)=N>>CC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C=2C=C(C=CC2)S(=O)(=O)N | O=[C:16](O)[c:15]1[cH:14][n:13][n:12]2[c:7]([C:8]([F:9])([F:10])[F:11])[cH:6][c:5](-[c:4]3[cH:3][c:2]([CH3:1])[c:35]([C:36]([F:37])([F:38])[F:39])[cH:34][cH:33]3)[n:32][c:31]21.[NH:17]=[C:18]([c:19]1[cH:20][cH:21][cH:22][c:23]([S:24]([NH2:25])(=[O:26])=[O:27])[cH:28]1)[NH:29][OH:30]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH... | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1cccc(S(N)(=O)=O)c1 | Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5cccc(S(N)(=O)=O)c5)no4)c3n2)ccc1C(F)(F)F | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:16]:[c:15]:[c;H0;D3;+0:14](-[c;H0;D3;+0:11]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2]2:[c:3]:[#7;a:4]:[#7;a:5](:... | null | [] | null | null | null | null | The title compound was prepared from 5-(3-methyl-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.8) (195 mg, 0.5 mmol) and N-hydroxy-3-sulfamoyl-benzamidine [CAS-No. 9000-88-7] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1cnc2ccnn2c1.c1ncon1.c1ccccc1 | HO- | null | null | null | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1cccc(S(N)(=O)=O)c1>>Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5cccc(S(N)(=O)=O)c5)no4)c3n2)ccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-97d831f3870b471cb7e10729771d00c8 | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(S(N)(=O)=O)cc1>>Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccc(S(N)(=O)=O)cc5)no4)c3n2)ccc1C(F)(F)F | CC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.ONC(C1=CC=C(C=C1)S(N)(=O)=O)=N>>CC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C2=CC=C(C=C2)S(=O)(=O)N | O=[C:16](O)[c:15]1[cH:14][n:13][n:12]2[c:7]([C:8]([F:9])([F:10])[F:11])[cH:6][c:5](-[c:4]3[cH:3][c:2]([CH3:1])[c:35]([C:36]([F:37])([F:38])[F:39])[cH:34][cH:33]3)[n:32][c:31]21.[NH:17]=[C:18]([c:19]1[cH:20][cH:21][c:22]([S:23]([NH2:24])(=[O:25])=[O:26])[cH:27][cH:28]1)[NH:29][OH:30]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH... | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(S(N)(=O)=O)cc1 | Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccc(S(N)(=O)=O)cc5)no4)c3n2)ccc1C(F)(F)F | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:16]:[c:15]:[c;H0;D3;+0:14](-[c;H0;D3;+0:11]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2]2:[c:3]:[#7;a:4]:[#7;a:5](:... | null | [] | null | null | null | null | The title compound was prepared from 5-(3-methyl-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.8) (195 mg, 0.5 mmol) and N-hydroxy-4-sulfamoyl-benzamidine [CAS-No. 4476-10-2] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1cnc2ccnn2c1.c1ncon1.c1ccccc1 | HO- | null | null | null | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(S(N)(=O)=O)cc1>>Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccc(S(N)(=O)=O)cc5)no4)c3n2)ccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-154a58628b2047f79764a15f9f8cd74c | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)c1 | ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)F)N=CC2C(=O)O.ONC(C1=CC(=CC=C1)S(N)(=O)=O)=N>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)F)N=CC2C2=NC(=NO2)C=2C=C(C=CC2)S(=O)(=O)N | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([NH:11][OH:12])=[NH:33])[cH:34]1.O=[C:13](O)[c:14]1[cH:15][n:16][n:17]2[c:18]([CH:19]([F:20])[F:21])[cH:22][c:23](-[c:24]3[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]3)[n:31][c:32]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9](-[c:10]2[n:11]... | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(Cl)cc3)nc12 | NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14](:[c:15]:[... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-phenyl)-7-difluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.3) (162 mg, 0.5 mmol) and N-hydroxy-3-sulfamoyl-benzamidine [CAS-No. 9000-88-7] (161 mg, 0.75 mmol) according to general procedure II. Obtained after trituration with water and further purifi... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b2722386cd254df5990ea9cdcc744f97 | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(Cl)cc5)nc34)n2)s1 | ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C1CC1)N=CC2C(=O)O.ONC(=N)C=1SC(=CC1)S(N)(=O)=O>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C1CC1)N=CC2C2=NC(=NO2)C2=CC=C(S2)S(=O)(=O)N | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:32])[s:33]1.O=[C:12](O)[c:13]1[cH:14][n:15][n:16]2[c:17]([CH:18]3[CH2:19][CH2:20]3)[cH:21][c:22](-[c:23]3[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]3)[n:30][c:31]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][o:11][c:12... | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(Cl)cc3)nc12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(Cl)cc5)nc34)n2)s1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2cc(C3CC3)n3ncc(-c4nc(-c5cccs5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[#16;a:15]:[c:16]:[c:17]:[c:18]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14]3:[#1... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.28) (157 mg, 0.5 mmol) and N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromatograph... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccsc1.c1ncon1.C1CC1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(Cl)cc5)nc34)n2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2f907553a91c4a0ab84dc1a408c8497b | N=C(NO)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12.NS(=O)(=O)c1ccc(C(=O)O)cc1>>NS(=O)(=O)c1ccc(-c2nc(-c3ncn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)no2)cc1 | ONC(=N)C=1N=CN2C1N=C(C=C2C(F)(F)F)C2=CC=C(C=C2)C(F)(F)F.S(N)(=O)(=O)C1=CC=C(C(=O)O)C=C1>>FC(C1=CC(=NC=2N1C=NC2C2=NOC(=N2)C2=CC=C(C=C2)S(=O)(=O)N)C2=CC=C(C=C2)C(F)(F)F)(F)F | [NH:10]=[C:11]([c:12]1[n:13][cH:14][n:15]2[c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][c:22](-[c:23]3[cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31][cH:32]3)[n:33][c:34]12)[NH:35][OH:36].O=[C:9](O)[c:8]1[cH:7][cH:6][c:5]([S:2]([NH2:1])(=[O:3])=[O:4])[cH:38][cH:37]1>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:... | N=C(NO)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12.NS(=O)(=O)c1ccc(C(=O)O)cc1 | NS(=O)(=O)c1ccc(-c2nc(-c3ncn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)no2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3cnc(-c4noc(-c5ccccc5)n4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH;D1;+0:7]=[C;H0;D3;+0:8](-[NH;D2;+0:9]-[OH;D1;+0:10])-[c;H0;D3;+0:11]1:[#7;a:12]:[c:13]:[#7;a:14](:[c:15]):[c:16]:1:[#7;a:17]:[c:18]>>[c:15]:[#7;a:14]1:[c:13]:[#7;a:12]:[c;H0;D3;+0:11](-[c;H0;D3;+0:8]2:[n;H0;D2;+0:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:... | null | [] | null | null | null | null | The title compound was prepared from N-hydroxy-4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxamidine (example B.3) (195 mg, 0.5 mmol) and commercially available 4-sulfamoyl-benzoic acid (101 mg, 0.5 mmol) according to general procedure II. Obtained after purification by column chromato... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1cnc2cncn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12.NS(=O)(=O)c1ccc(C(=O)O)cc1>>NS(=O)(=O)c1ccc(-c2nc(-c3ncn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)no2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb1c13aa025442efa37be7e44707c2a7 | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(S(N)(=O)=O)s1>>Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccc(S(N)(=O)=O)s5)no4)c3n2)ccc1C(F)(F)F | CC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.ONC(=N)C=1SC(=CC1)S(N)(=O)=O>>CC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C2=CC=C(S2)S(=O)(=O)N | O=[C:16](O)[c:15]1[cH:14][n:13][n:12]2[c:7]([C:8]([F:9])([F:10])[F:11])[cH:6][c:5](-[c:4]3[cH:3][c:2]([CH3:1])[c:34]([C:35]([F:36])([F:37])[F:38])[cH:33][cH:32]3)[n:31][c:30]21.[NH:17]=[C:18]([c:19]1[cH:20][cH:21][c:22]([S:23]([NH2:24])(=[O:25])=[O:26])[s:27]1)[NH:28][OH:29]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]... | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(S(N)(=O)=O)s1 | Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccc(S(N)(=O)=O)s5)no4)c3n2)ccc1C(F)(F)F | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccs5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[#16;a:15]:[c:16]:[c:17]:[c:18]:1>>[c:9]:[#7;a:8]:[c:7]1:[#7;a:5](:[c:6]):[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:1... | null | [] | null | null | null | null | The title compound was prepared from 5-(3-methyl-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.8) (195 mg, 0.5 mmol) and N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) according to general procedure II. Obtained after purification b... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1cnc2ccnn2c1.c1ncon1.c1ccsc1 | HO- | null | null | null | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(S(N)(=O)=O)s1>>Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccc(S(N)(=O)=O)s5)no4)c3n2)ccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bbdd9f4ce6a6412095313a69fe0c5720 | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(OCC(F)(F)F)c3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(OCC(F)(F)F)c5)nc34)n2)s1 | FC(COC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O)(F)F.ONC(=N)C=1SC(=CC1)S(N)(=O)=O>>FC(COC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C2=CC=C(S2)S(=O)(=O)N)(F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:42])[s:43]1.O=[C:12](O)[c:13]1[cH:14][n:15][n:16]2[c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][c:23](-[c:24]3[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[c:32]([O:33][CH2:34][C:35]([F:36])([F:37])[F:38])[cH:39]3)[n:40][c:41]12>>[NH2:1][S... | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(OCC(F)(F)F)c3)nc12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(OCC(F)(F)F)c5)nc34)n2)s1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccs5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[#16;a:15]:[c:16]:[c:17]:[c:18]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14]3:[#1... | null | [] | null | null | null | null | The title compound was prepared from 5-[3-(2,2,2-trifluoro-ethoxy)-4-trifluoromethyl-phenyl]-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.10) (237 mg, 0.5 mmol) and N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) according to general procedure II. Obtained a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccsc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)c(OCC(F)(F)F)c3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)c(OCC(F)(F)F)c5)nc34)n2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a07b40863f6a45c181ec20897f2482e8 | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)s1 | C1(CC1)C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F.ONC(=N)C=1SC(=CC1)S(N)(=O)=O>>C1(CC1)C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C2=CC=C(S2)S(=O)(=O)N)C2=CC=C(C=C2)C(F)(F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:35])[s:36]1.O=[C:12](O)[c:13]1[cH:14][n:15][n:16]2[c:17]([CH:18]3[CH2:19][CH2:20]3)[cH:21][c:22](-[c:23]3[cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31][cH:32]3)[n:33][c:34]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c... | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(C(F)(F)F)cc3)nc12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)s1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2cc(C3CC3)n3ncc(-c4nc(-c5cccs5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[#16;a:15]:[c:16]:[c:17]:[c:18]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14]3:[#1... | null | [] | null | null | null | null | The title compound was prepared from 7-cyclopropyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.29) (174 mg, 0.5 mmol) N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) and according to general procedure II. Obtained after purification by flash chro... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccsc1.c1ncon1.C1CC1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C3CC3)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C5CC5)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-470313e047344697a0414acf5cef8d1e | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3cccc(C(F)(F)F)c3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5cccc(C(F)(F)F)c5)nc34)n2)cc1 | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC(=CC=C2)C(F)(F)F)(F)F.ONC(C1=CC=C(C=C1)S(N)(=O)=O)=N>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C2=CC=C(C=C2)S(=O)(=O)N)C2=CC(=CC=C2)C(F)(F)F)(F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:36])[cH:37][cH:38]1.O=[C:12](O)[c:13]1[cH:14][n:15][n:16]2[c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][c:23](-[c:24]3[cH:25][cH:26][cH:27][c:28]([C:29]([F:30])([F:31])[F:32])[cH:33]3)[n:34][c:35]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:... | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3cccc(C(F)(F)F)c3)nc12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5cccc(C(F)(F)F)c5)nc34)n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14](:[c:15]:[... | null | [] | null | null | null | null | The title compound was prepared from 7-trifluoromethyl-5-(3-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.31) (188 mg, 0.5 mmol) and N-hydroxy-4-sulfamoyl-benzamidine [CAS-No. 4476-10-2] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromato... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3cccc(C(F)(F)F)c3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5cccc(C(F)(F)F)c5)nc34)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-af00ccfc4eaf4e77adac820f80599162 | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3cccc(C(F)(F)F)c3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5cccc(C(F)(F)F)c5)nc34)n2)c1 | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC(=CC=C2)C(F)(F)F)(F)F.ONC(C1=CC(=CC=C1)S(N)(=O)=O)=N>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C=2C=C(C=CC2)S(=O)(=O)N)C2=CC(=CC=C2)C(F)(F)F)(F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([NH:11][OH:12])=[NH:37])[cH:38]1.O=[C:13](O)[c:14]1[cH:15][n:16][n:17]2[c:18]([C:19]([F:20])([F:21])[F:22])[cH:23][c:24](-[c:25]3[cH:26][cH:27][cH:28][c:29]([C:30]([F:31])([F:32])[F:33])[cH:34]3)[n:35][c:36]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:... | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3cccc(C(F)(F)F)c3)nc12 | NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5cccc(C(F)(F)F)c5)nc34)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14](:[c:15]:[... | null | [] | null | null | null | null | The title compound was prepared from 7-trifluoromethyl-5-(3-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.31) (188 mg, 0.5 mmol) and N-hydroxy-3-sulfamoyl-benzamidine [CAS-No. 9000-88-7] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromato... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3cccc(C(F)(F)F)c3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5cccc(C(F)(F)F)c5)nc34)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3617e3e4364c4fe2916df5d0c30f2d25 | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)s1 | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)(F)F.ONC(=N)C=1SC(=CC1)S(N)(=O)=O>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C2=CC=C(S2)S(=O)(=O)N)C2=CC=C(C=C2)C(F)(F)F)(F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:36])[s:37]1.O=[C:12](O)[c:13]1[cH:14][n:15][n:16]2[c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][c:23](-[c:24]3[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]3)[n:34][c:35]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](... | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)s1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccs5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[#16;a:15]:[c:16]:[c:17]:[c:18]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14]3:[#1... | null | [] | null | null | null | null | The title compound was prepared from 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.2) (188 mg, 0.5 mmol) and N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash c... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccsc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cfb40ef77def4cc0bd8b648146c712a6 | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)s1 | ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.ONC(=N)C=1SC(=CC1)S(N)(=O)=O>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C2=CC=C(S2)S(=O)(=O)N | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:33])[s:34]1.O=[C:12](O)[c:13]1[cH:14][n:15][n:16]2[c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][c:23](-[c:24]3[cH:25][cH:26][c:27]([Cl:28])[cH:29][cH:30]3)[n:31][c:32]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][o:11][c... | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)s1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccs5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[#16;a:15]:[c:16]:[c:17]:[c:18]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14]3:[#1... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.4) (171 mg, 0.5 mmol) and N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromatogr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccsc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cce2b0cecfea4f638b8547cacfb2f899 | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)s1 | ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)F)N=CC2C(=O)O.ONC(=N)C=1SC(=CC1)S(N)(=O)=O>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)F)N=CC2C2=NC(=NO2)C2=CC=C(S2)S(=O)(=O)N | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:32])[s:33]1.O=[C:12](O)[c:13]1[cH:14][n:15][n:16]2[c:17]([CH:18]([F:19])[F:20])[cH:21][c:22](-[c:23]3[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]3)[n:30][c:31]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][o:11][c:12](-[... | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(Cl)cc3)nc12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)s1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccs5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[#16;a:15]:[c:16]:[c:17]:[c:18]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14]3:[#1... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-phenyl)-7-difluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.3) (162 mg, 0.5 mmol) and N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromatogra... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccsc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a90f0e1c0e544b3befe24b019a6fc36 | Cc1cc(-c2ccc(C(F)(F)F)cc2)nc2c(C(=O)O)cnn12.N=C(NO)c1ccc(S(N)(=O)=O)s1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)nc2c(-c3nc(-c4ccc(S(N)(=O)=O)s4)no3)cnn12 | CC1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F.ONC(=N)C=1SC(=CC1)S(N)(=O)=O>>CC1=CC(=NC=2N1N=CC2C2=NC(=NO2)C2=CC=C(S2)S(=O)(=O)N)C2=CC=C(C=C2)C(F)(F)F | O=[C:18](O)[c:17]1[c:16]2[n:15][c:4](-[c:5]3[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]3)[cH:3][c:2]([CH3:1])[n:34]2[n:33][cH:32]1.[NH:19]=[C:20]([c:21]1[cH:22][cH:23][c:24]([S:25]([NH2:26])(=[O:27])=[O:28])[s:29]1)[NH:30][OH:31]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[... | Cc1cc(-c2ccc(C(F)(F)F)cc2)nc2c(C(=O)O)cnn12.N=C(NO)c1ccc(S(N)(=O)=O)s1 | Cc1cc(-c2ccc(C(F)(F)F)cc2)nc2c(-c3nc(-c4ccc(S(N)(=O)=O)s4)no3)cnn12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccs5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[#16;a:15]:[c:16]:[c:17]:[c:18]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14]3:[#1... | null | [] | null | null | null | null | The title compound was prepared from 7-methyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.25) (161 mg, 0.5 mmol) and N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromato... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1ccsc1.c1cnc2ccnn2c1 | HO- | null | null | null | Cc1cc(-c2ccc(C(F)(F)F)cc2)nc2c(C(=O)O)cnn12.N=C(NO)c1ccc(S(N)(=O)=O)s1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)nc2c(-c3nc(-c4ccc(S(N)(=O)=O)s4)no3)cnn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f3ea66781a1c4b71bf95a8737988cd09 | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)s1 | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)F.ONC(=N)C=1SC(=CC1)S(N)(=O)=O>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C2=CC=C(S2)S(=O)(=O)N)C2=CC=C(C=C2)C(F)(F)F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:35])[s:36]1.O=[C:12](O)[c:13]1[cH:14][n:15][n:16]2[c:17]([CH:18]([F:19])[F:20])[cH:21][c:22](-[c:23]3[cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31][cH:32]3)[n:33][c:34]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2... | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)s1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccs5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[#16;a:15]:[c:16]:[c:17]:[c:18]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14]3:[#1... | null | [] | null | null | null | null | The title compound was prepared from 7-difluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.1) (179 mg, 0.5 mmol) and N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash ch... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccsc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-efcb53f71b1e434bb3f3d3ec5909f8cf | Cc1cc(-c2ccc(Cl)cc2)nc2c(C(=O)O)cnn12.N=C(NO)c1ccc(S(N)(=O)=O)s1>>Cc1cc(-c2ccc(Cl)cc2)nc2c(-c3nc(-c4ccc(S(N)(=O)=O)s4)no3)cnn12 | ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C)N=CC2C(=O)O.ONC(=N)C=1SC(=CC1)S(N)(=O)=O>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C)N=CC2C2=NC(=NO2)C2=CC=C(S2)S(=O)(=O)N | O=[C:15](O)[c:14]1[c:13]2[n:12][c:4](-[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[cH:3][c:2]([CH3:1])[n:31]2[n:30][cH:29]1.[NH:16]=[C:17]([c:18]1[cH:19][cH:20][c:21]([S:22]([NH2:23])(=[O:24])=[O:25])[s:26]1)[NH:27][OH:28]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[n:12][c:13]2[c:14](... | Cc1cc(-c2ccc(Cl)cc2)nc2c(C(=O)O)cnn12.N=C(NO)c1ccc(S(N)(=O)=O)s1 | Cc1cc(-c2ccc(Cl)cc2)nc2c(-c3nc(-c4ccc(S(N)(=O)=O)s4)no3)cnn12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccs5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[#16;a:15]:[c:16]:[c:17]:[c:18]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14]3:[#1... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-phenyl)-7-methyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.24) (144 mg, 0.5 mmol) and N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromatography (d... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1ccsc1.c1cnc2ccnn2c1 | HO- | null | null | null | Cc1cc(-c2ccc(Cl)cc2)nc2c(C(=O)O)cnn12.N=C(NO)c1ccc(S(N)(=O)=O)s1>>Cc1cc(-c2ccc(Cl)cc2)nc2c(-c3nc(-c4ccc(S(N)(=O)=O)s4)no3)cnn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-89765bbd464041f28ed5313591f36569 | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3cccc(C(F)(F)F)c3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5cccc(C(F)(F)F)c5)nc34)n2)cn1 | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC(=CC=C2)C(F)(F)F)(F)F.NC1=NC=C(C(=N)NO)C=C1>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N)C2=CC(=CC=C2)C(F)(F)F)(F)F | [NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:33])[cH:34][n:35]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][c:20](-[c:21]3[cH:22][cH:23][cH:24][c:25]([C:26]([F:27])([F:28])[F:29])[cH:30]3)[n:31][c:32]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]3[cH:11]... | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3cccc(C(F)(F)F)c3)nc12 | Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5cccc(C(F)(F)F)c5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[c:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14... | null | [] | null | null | null | null | The title compound was prepared from 7-trifluoromethyl-5-(3-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.31) (188 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromatography ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3cccc(C(F)(F)F)c3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5cccc(C(F)(F)F)c5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0321eae42ad843199b7b8e0cba2bf101 | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cn1 | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)(F)F.NC1=NC=C(C(=N)NO)C=C1>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N)C2=CC=C(C=C2)C(F)(F)F)(F)F | [NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:33])[cH:34][n:35]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[cH:29][cH:30]3)[n:31][c:32]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]3[cH:11]... | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[c:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14... | null | [] | null | null | null | null | The title compound was prepared from 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.2) (188 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromatography (... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c2b72599ebbf439286d737717a79bf44 | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cn1 | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)F.NC1=NC=C(C(=N)NO)C=C1>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N)C2=CC=C(C=C2)C(F)(F)F)F | [NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:32])[cH:33][n:34]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([CH:15]([F:16])[F:17])[cH:18][c:19](-[c:20]3[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28][cH:29]3)[n:30][c:31]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]3[cH:11][n:12][... | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[c:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14... | null | [] | null | null | null | null | The title compound was prepared from 7-difluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.1) (179 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromatography (e... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6291c16266e447d699493b6bcef5bbae | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(N)nc1>>Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1C(F)(F)F | CC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.NC1=NC=C(C(=N)NO)C=C1>>CC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N | O=[C:16](O)[c:15]1[cH:14][n:13][n:12]2[c:7]([C:8]([F:9])([F:10])[F:11])[cH:6][c:5](-[c:4]3[cH:3][c:2]([CH3:1])[c:32]([C:33]([F:34])([F:35])[F:36])[cH:31][cH:30]3)[n:29][c:28]21.[NH:17]=[C:18]([c:19]1[cH:20][cH:21][c:22]([NH2:23])[n:24][cH:25]1)[NH:26][OH:27]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([C:8]([F:9])([F:... | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(N)nc1 | Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1C(F)(F)F | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[c:16]:[c:17]:[#7;a:18]:[c:19]:1>>[c:9]:[#7;a:8]:[c:7]1:[#7;a:5](:[c:6]):[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c;H0;D... | null | [] | null | null | null | null | The title compound was prepared from 5-(3-methyl-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.8) (195 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1cnc2ccnn2c1.c1ncon1.c1ccncc1 | HO- | null | null | null | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(N)nc1>>Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc5a3ca5c20c49c8949427dbd3c6901b | Cc1cc(-c2ccc(Cl)cc2)nc2c(C(=O)O)cnn12.N=C(NO)c1cccc(S(N)(=O)=O)c1>>Cc1cc(-c2ccc(Cl)cc2)nc2c(-c3nc(-c4cccc(S(N)(=O)=O)c4)no3)cnn12 | ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C)N=CC2C(=O)O.ONC(C1=CC(=CC=C1)S(N)(=O)=O)=N>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C)N=CC2C2=NC(=NO2)C=2C=C(C=CC2)S(=O)(=O)N | O=[C:15](O)[c:14]1[c:13]2[n:12][c:4](-[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[cH:3][c:2]([CH3:1])[n:32]2[n:31][cH:30]1.[NH:16]=[C:17]([c:18]1[cH:19][cH:20][cH:21][c:22]([S:23]([NH2:24])(=[O:25])=[O:26])[cH:27]1)[NH:28][OH:29]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[n:12][c:13]... | Cc1cc(-c2ccc(Cl)cc2)nc2c(C(=O)O)cnn12.N=C(NO)c1cccc(S(N)(=O)=O)c1 | Cc1cc(-c2ccc(Cl)cc2)nc2c(-c3nc(-c4cccc(S(N)(=O)=O)c4)no3)cnn12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:16]:[c:15]:[c;H0;D3;+0:14](-[c;H0;D3;+0:11]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2]2:[c:3]:[#7;a:4]:[#7;a:5](:... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-phenyl)-7-methyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.24) (144 mg, 0.5 mmol) and N-hydroxy-3-sulfamoyl-benzamidine [CAS-No. 9000-88-7] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromatography (ethyl acet... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1ccccc1.c1cnc2ccnn2c1 | HO- | null | null | null | Cc1cc(-c2ccc(Cl)cc2)nc2c(C(=O)O)cnn12.N=C(NO)c1cccc(S(N)(=O)=O)c1>>Cc1cc(-c2ccc(Cl)cc2)nc2c(-c3nc(-c4cccc(S(N)(=O)=O)c4)no3)cnn12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bf952b3f913d4a379580606f0dba7bb6 | Cc1cc(-c2ccc(Cl)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccc(S(N)(=O)=O)cc1>>Cc1cc(-c2ccc(Cl)cc2)cn2c(-c3nc(-c4ccc(S(N)(=O)=O)cc4)no3)cnc12 | ClC1=CC=C(C=C1)C=1C=C(C=2N(C1)C(=CN2)C(=O)O)C.ONC(C1=CC=C(C=C1)S(N)(=O)=O)=N>>ClC1=CC=C(C=C1)C=1C=C(C=2N(C1)C(=CN2)C2=NC(=NO2)C2=CC=C(C=C2)S(=O)(=O)N)C | O=[C:15](O)[c:14]1[n:13]2[cH:12][c:4](-[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[cH:3][c:2]([CH3:1])[c:32]2[n:31][cH:30]1.[NH:16]=[C:17]([c:18]1[cH:19][cH:20][c:21]([S:22]([NH2:23])(=[O:24])=[O:25])[cH:26][cH:27]1)[NH:28][OH:29]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[cH:12][n:1... | Cc1cc(-c2ccc(Cl)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccc(S(N)(=O)=O)cc1 | Cc1cc(-c2ccc(Cl)cc2)cn2c(-c3nc(-c4ccc(S(N)(=O)=O)cc4)no3)cnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5ccccc5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1:[c:7].[NH;D1;+0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[OH;D1;+0:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[c:7]:[#7;a:6]1:[c:5]:[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:9](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:... | null | [] | null | null | null | null | The title compound was prepared from 6-(4-chloro-phenyl)-8-methyl-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.33) (143 mg, 0.5 mmol) and N-hydroxy-4-sulfamoyl-benzamidine [CAS-No. 4476-10-2] (161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromatography (ethyl acetate... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1ccccc1.c1ccn2ccnc2c1 | HO- | null | null | null | Cc1cc(-c2ccc(Cl)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccc(S(N)(=O)=O)cc1>>Cc1cc(-c2ccc(Cl)cc2)cn2c(-c3nc(-c4ccc(S(N)(=O)=O)cc4)no3)cnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f42316cf41b547538b54ca7f9be347cf | Cc1cc(-c2ccc(Cl)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1cccc(S(N)(=O)=O)c1>>Cc1cc(-c2ccc(Cl)cc2)cn2c(-c3nc(-c4cccc(S(N)(=O)=O)c4)no3)cnc12 | ClC1=CC=C(C=C1)C=1C=C(C=2N(C1)C(=CN2)C(=O)O)C.ONC(C1=CC(=CC=C1)S(N)(=O)=O)=N>>ClC1=CC=C(C=C1)C=1C=C(C=2N(C1)C(=CN2)C2=NC(=NO2)C=2C=C(C=CC2)S(=O)(=O)N)C | O=[C:15](O)[c:14]1[n:13]2[cH:12][c:4](-[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[cH:3][c:2]([CH3:1])[c:32]2[n:31][cH:30]1.[NH:16]=[C:17]([c:18]1[cH:19][cH:20][cH:21][c:22]([S:23]([NH2:24])(=[O:25])=[O:26])[cH:27]1)[NH:28][OH:29]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[cH:12][n:1... | Cc1cc(-c2ccc(Cl)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1cccc(S(N)(=O)=O)c1 | Cc1cc(-c2ccc(Cl)cc2)cn2c(-c3nc(-c4cccc(S(N)(=O)=O)c4)no3)cnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5ccccc5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1:[c:7].[NH;D1;+0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[OH;D1;+0:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[c:7]:[#7;a:6]1:[c:5]:[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:9](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:... | null | [] | null | null | null | null | The title compound was prepared from 6-(4-chloro-phenyl)-8-methyl-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.33) (143 mg, 0.5 mmol) and N-hydroxy-3-sulfamoyl-benzamidine [CAS-No. 9000-88-7] (161 mg, 0.75 mmol) according to general procedure II. Obtained after trituration with water and further purification by ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1ccccc1.c1ccn2ccnc2c1 | HO- | null | null | null | Cc1cc(-c2ccc(Cl)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1cccc(S(N)(=O)=O)c1>>Cc1cc(-c2ccc(Cl)cc2)cn2c(-c3nc(-c4cccc(S(N)(=O)=O)c4)no3)cnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5e66a0b5a15e4f69820d45fe76accc64 | Cc1cc(-c2ccc(Cl)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccc(S(N)(=O)=O)s1>>Cc1cc(-c2ccc(Cl)cc2)cn2c(-c3nc(-c4ccc(S(N)(=O)=O)s4)no3)cnc12 | ClC1=CC=C(C=C1)C=1C=C(C=2N(C1)C(=CN2)C(=O)O)C.ONC(=N)C=1SC(=CC1)S(N)(=O)=O>>ClC1=CC=C(C=C1)C=1C=C(C=2N(C1)C(=CN2)C2=NC(=NO2)C2=CC=C(S2)S(=O)(=O)N)C | O=[C:15](O)[c:14]1[n:13]2[cH:12][c:4](-[c:5]3[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]3)[cH:3][c:2]([CH3:1])[c:31]2[n:30][cH:29]1.[NH:16]=[C:17]([c:18]1[cH:19][cH:20][c:21]([S:22]([NH2:23])(=[O:24])=[O:25])[s:26]1)[NH:27][OH:28]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([Cl:9])[cH:10][cH:11]2)[cH:12][n:13]2[c:14... | Cc1cc(-c2ccc(Cl)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccc(S(N)(=O)=O)s1 | Cc1cc(-c2ccc(Cl)cc2)cn2c(-c3nc(-c4ccc(S(N)(=O)=O)s4)no3)cnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5cccs5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1:[c:7].[NH;D1;+0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[OH;D1;+0:11])-[c;H0;D3;+0:12]1:[#16;a:13]:[c:14]:[c:15]:[c:16]:1>>[c:7]:[#7;a:6]1:[c:5]:[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:9](-[c;H0;D3;+0:12]2:[#16;a:13]:[c:14]... | null | [] | null | null | null | null | The title compound was prepared from 6-(4-chloro-phenyl)-8-methyl-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.33) (143 mg, 0.5 mmol) and N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) according to general procedure II. Obtained after trituration with water and further purifica... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1ccsc1.c1ccn2ccnc2c1 | HO- | null | null | null | Cc1cc(-c2ccc(Cl)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccc(S(N)(=O)=O)s1>>Cc1cc(-c2ccc(Cl)cc2)cn2c(-c3nc(-c4ccc(S(N)(=O)=O)s4)no3)cnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d3d7fdb6c8f4eedb66d5bf1a1b7f70d | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3ncn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)s1 | FC(C1=CC(=NC=2N1C=NC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)(F)F.ONC(=N)C=1SC(=CC1)S(N)(=O)=O>>FC(C1=CC(=NC=2N1C=NC2C2=NC(=NO2)C2=CC=C(S2)S(=O)(=O)N)C2=CC=C(C=C2)C(F)(F)F)(F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:36])[s:37]1.O=[C:12](O)[c:13]1[n:14][cH:15][n:16]2[c:17]([C:18]([F:19])([F:20])[F:21])[cH:22][c:23](-[c:24]3[cH:25][cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32][cH:33]3)[n:34][c:35]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](... | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | NS(=O)(=O)c1ccc(-c2noc(-c3ncn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)s1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3cnc(-c4nc(-c5cccs5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[#16;a:15]:[c:16]:[c:17]:[c:18]:1>>[c:6]:[#7;a:5]1:[c:4]:[#7;a:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14]3:[#1... | null | [] | null | null | null | null | The title compound was prepared from 4-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-imidazo[1,5-a]pyrimidine-8-carboxylic acid (example C.30) (188 mg, 0.5 mmol) and N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash c... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccsc1.c1ncon1.c1cnc2cncn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1ncn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>NS(=O)(=O)c1ccc(-c2noc(-c3ncn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-17e584b6801e4e7f8cd6ff4acdf41b14 | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccc(S(N)(=O)=O)cc1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4ccc(S(N)(=O)=O)cc4)no3)cnc12 | CC=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C(=O)O.ONC(C1=CC=C(C=C1)S(N)(=O)=O)=N>>CC=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C2=NC(=NO2)C2=CC=C(C=C2)S(=O)(=O)N | O=[C:18](O)[c:17]1[n:16]2[cH:15][c:4](-[c:5]3[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]3)[cH:3][c:2]([CH3:1])[c:35]2[n:34][cH:33]1.[NH:19]=[C:20]([c:21]1[cH:22][cH:23][c:24]([S:25]([NH2:26])(=[O:27])=[O:28])[cH:29][cH:30]1)[NH:31][OH:32]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])... | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccc(S(N)(=O)=O)cc1 | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4ccc(S(N)(=O)=O)cc4)no3)cnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5ccccc5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1:[c:7].[NH;D1;+0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[OH;D1;+0:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[c:7]:[#7;a:6]1:[c:5]:[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:9](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:... | null | [] | null | null | null | null | The title compound was prepared from 8-methyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.34) (160 mg, 0.5 mmol) and N-hydroxy-4-sulfamoyl-benzamidine [CAS-No. 4476-10-2](161 mg, 0.75 mmol) according to general procedure II. Obtained after trituration with water and further purifica... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1ccccc1.c1ccn2ccnc2c1 | HO- | null | null | null | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccc(S(N)(=O)=O)cc1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4ccc(S(N)(=O)=O)cc4)no3)cnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b7264b953284980be4adc5080234d94 | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1cccc(S(N)(=O)=O)c1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4cccc(S(N)(=O)=O)c4)no3)cnc12 | CC=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C(=O)O.ONC(C1=CC(=CC=C1)S(N)(=O)=O)=N>>CC=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C2=NC(=NO2)C=2C=C(C=CC2)S(=O)(=O)N | O=[C:18](O)[c:17]1[n:16]2[cH:15][c:4](-[c:5]3[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]3)[cH:3][c:2]([CH3:1])[c:35]2[n:34][cH:33]1.[NH:19]=[C:20]([c:21]1[cH:22][cH:23][cH:24][c:25]([S:26]([NH2:27])(=[O:28])=[O:29])[cH:30]1)[NH:31][OH:32]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])... | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1cccc(S(N)(=O)=O)c1 | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4cccc(S(N)(=O)=O)c4)no3)cnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5ccccc5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1:[c:7].[NH;D1;+0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[OH;D1;+0:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16]>>[c:7]:[#7;a:6]1:[c:5]:[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:9](-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:... | null | [] | null | null | null | null | The title compound was prepared from 8-methyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.34) (160 mg, 0.5 mmol) and N-hydroxy-3-sulfamoyl-benzamidine [CAS-No. 9000-88-7] (161 mg, 0.75 mmol) according to general procedure II. Obtained after trituration with water and further purific... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1ccccc1.c1ccn2ccnc2c1 | HO- | null | null | null | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1cccc(S(N)(=O)=O)c1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4cccc(S(N)(=O)=O)c4)no3)cnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d7c1fc8246b64559b81632fdaf477626 | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccc(S(N)(=O)=O)s1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4ccc(S(N)(=O)=O)s4)no3)cnc12 | CC=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C(=O)O.ONC(=N)C=1SC(=CC1)S(N)(=O)=O>>CC=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C2=NC(=NO2)C2=CC=C(S2)S(=O)(=O)N | O=[C:18](O)[c:17]1[n:16]2[cH:15][c:4](-[c:5]3[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]3)[cH:3][c:2]([CH3:1])[c:34]2[n:33][cH:32]1.[NH:19]=[C:20]([c:21]1[cH:22][cH:23][c:24]([S:25]([NH2:26])(=[O:27])=[O:28])[s:29]1)[NH:30][OH:31]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])... | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccc(S(N)(=O)=O)s1 | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4ccc(S(N)(=O)=O)s4)no3)cnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5cccs5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1:[c:7].[NH;D1;+0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[OH;D1;+0:11])-[c;H0;D3;+0:12]1:[#16;a:13]:[c:14]:[c:15]:[c:16]:1>>[c:7]:[#7;a:6]1:[c:5]:[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:9](-[c;H0;D3;+0:12]2:[#16;a:13]:[c:14]... | null | [] | null | null | null | null | The title compound was prepared from 8-methyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.34) (160 mg, 0.5 mmol) and N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromatogra... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1ccsc1.c1ccn2ccnc2c1 | HO- | null | null | null | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccc(S(N)(=O)=O)s1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4ccc(S(N)(=O)=O)s4)no3)cnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-136e60e3a75f452c84ca7b266eb28c1d | N=C(NO)c1cnc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>Nc1ncc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cn1 | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)(F)F.NC1=NC=C(C=N1)C(=N)NO>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C=2C=NC(=NC2)N)C2=CC=C(C=C2)C(F)(F)F)(F)F | [NH2:1][c:2]1[n:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:33])[cH:34][n:35]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[cH:29][cH:30]3)[n:31][c:32]12>>[NH2:1][c:2]1[n:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]3[cH:11][n... | N=C(NO)c1cnc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | Nc1ncc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cncnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[#7;a:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0... | null | [] | null | null | null | null | The title compound was prepared from 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.2) (188 mg, 0.5 mmol) 2-amino-N-hydroxy-pyrimidine-5-carboxamidine (example B.5) (115 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromato... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1cncnc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cnc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>Nc1ncc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-95f34cd410114728b25eea5412ce9788 | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccc(N)nc1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4ccc(N)nc4)no3)cnc12 | CC=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C(=O)O.NC1=NC=C(C(=N)NO)C=C1>>CC=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C2=NC(=NO2)C=2C=CC(=NC2)N | O=[C:18](O)[c:17]1[n:16]2[cH:15][c:4](-[c:5]3[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]3)[cH:3][c:2]([CH3:1])[c:32]2[n:31][cH:30]1.[NH:19]=[C:20]([c:21]1[cH:22][cH:23][c:24]([NH2:25])[n:26][cH:27]1)[NH:28][OH:29]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH... | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccc(N)nc1 | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4ccc(N)nc4)no3)cnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5cccnc5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1:[c:7].[NH;D1;+0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[OH;D1;+0:11])-[c;H0;D3;+0:12]1:[c:13]:[c:14]:[c:15]:[#7;a:16]:[c:17]:1>>[c:7]:[#7;a:6]1:[c:5]:[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:9](-[c;H0;D3;+0:12]2:[c:13]:[c:1... | null | [] | null | null | null | null | The title compound was prepared from 8-methyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.34) (160 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromatography (dichlorome... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1ccncc1.c1ccn2ccnc2c1 | HO- | null | null | null | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccc(N)nc1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4ccc(N)nc4)no3)cnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6c59ebf3302a427ca1e77ba9d7d98242 | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1cnc(N)nc1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4cnc(N)nc4)no3)cnc12 | CC=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C(=O)O.NC1=NC=C(C=N1)C(=N)NO>>CC=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C2=NC(=NO2)C=2C=NC(=NC2)N | O=[C:18](O)[c:17]1[n:16]2[cH:15][c:4](-[c:5]3[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]3)[cH:3][c:2]([CH3:1])[c:32]2[n:31][cH:30]1.[NH:19]=[C:20]([c:21]1[cH:22][n:23][c:24]([NH2:25])[n:26][cH:27]1)[NH:28][OH:29]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:... | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1cnc(N)nc1 | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4cnc(N)nc4)no3)cnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5cncnc5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1:[c:7].[NH;D1;+0:8]=[C;H0;D3;+0:9](-[NH;D2;+0:10]-[OH;D1;+0:11])-[c;H0;D3;+0:12]1:[c:13]:[#7;a:14]:[c:15]:[#7;a:16]:[c:17]:1>>[c:7]:[#7;a:6]1:[c:5]:[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:8]:[c;H0;D3;+0:9](-[c;H0;D3;+0:12]2:[c:13]:[... | null | [] | null | null | null | null | The title compound was prepared from 8-methyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.34) (160 mg, 0.5 mmol) 2-amino-N-hydroxy-pyrimidine-5-carboxamidine (example B.5) (115 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromatography (eth... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1cncnc1.c1ccn2ccnc2c1 | HO- | null | null | null | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1cnc(N)nc1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4cnc(N)nc4)no3)cnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b2e63a77529e4061963ba3c94cc85f1e | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2ccc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4ccc(-c5ccc(Cl)cc5)nc34)n2)c1 | ClC1=CC=C(C=C1)C1=NC=2N(C=C1)N=CC2C(=O)O.ONC(C1=CC(=CC=C1)S(N)(=O)=O)=N>>ClC1=CC=C(C=C1)C1=NC=2N(C=C1)N=CC2C2=NC(=NO2)C=2C=C(C=CC2)S(=O)(=O)N | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([NH:11][OH:12])=[NH:30])[cH:31]1.O=[C:13](O)[c:14]1[cH:15][n:16][n:17]2[cH:18][cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]3)[n:28][c:29]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9](-[c:10]2[n:11][o:12][c:13](-[c:14]3[... | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2ccc(-c3ccc(Cl)cc3)nc12 | NS(=O)(=O)c1cccc(-c2noc(-c3cnn4ccc(-c5ccc(Cl)cc5)nc34)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccccc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14](:[c:15]:[c:16]):[c:17]:[c:18]>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14](:[c:15]:[... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.22) (137 mg, 0.5 mmol) and N-hydroxy-3-sulfamoyl-benzamidine [CAS-No. 9000-88-7](161 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromatography (dichloromethane/MeOH... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnn2ccc(-c3ccc(Cl)cc3)nc12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnn4ccc(-c5ccc(Cl)cc5)nc34)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-69860798dd4b48bba3b519550115b5ad | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnc2ccc(-c3ccc(C(F)(F)F)cc3)cn12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnc4ccc(-c5ccc(C(F)(F)F)cc5)cn34)n2)cc1 | FC(C1=CC=C(C=C1)C=1C=CC=2N(C1)C(=CN2)C(=O)O)(F)F.ONC(C1=CC=C(C=C1)S(N)(=O)=O)=N>>FC(C1=CC=C(C=C1)C=1C=CC=2N(C1)C(=CN2)C2=NC(=NO2)C2=CC=C(C=C2)S(=O)(=O)N)(F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:32])[cH:33][cH:34]1.O=[C:12](O)[c:13]1[cH:14][n:15][c:16]2[cH:17][cH:18][c:19](-[c:20]3[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28][cH:29]3)[cH:30][n:31]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][o:11][... | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnc2ccc(-c3ccc(C(F)(F)F)cc3)cn12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnc4ccc(-c5ccc(C(F)(F)F)cc5)cn34)n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5ccccc5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5](:[c:6]):[#7;a:7]:1:[c:8].[NH;D1;+0:9]=[C;H0;D3;+0:10](-[NH;D2;+0:11]-[OH;D1;+0:12])-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:9]:[c;H0;D3;+0:10](-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:... | null | [] | null | null | null | null | The title compound was prepared from 6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.35) (153 mg, 0.5 mmol) and N-hydroxy-4-sulfamoyl-benzamidine [CAS-No. 4476-10-2] (161 mg, 0.75 mmol) according to general procedure II. Obtained after trituration with water and further purification by ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1ccn2ccnc2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)cc1.O=C(O)c1cnc2ccc(-c3ccc(C(F)(F)F)cc3)cn12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnc4ccc(-c5ccc(C(F)(F)F)cc5)cn34)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3e6b86a844d54adfaa41b72a7fcd373c | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnc2ccc(-c3ccc(C(F)(F)F)cc3)cn12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnc4ccc(-c5ccc(C(F)(F)F)cc5)cn34)n2)c1 | FC(C1=CC=C(C=C1)C=1C=CC=2N(C1)C(=CN2)C(=O)O)(F)F.ONC(C1=CC(=CC=C1)S(N)(=O)=O)=N>>FC(C1=CC=C(C=C1)C=1C=CC=2N(C1)C(=CN2)C2=NC(=NO2)C=2C=C(C=CC2)S(=O)(=O)N)(F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([NH:11][OH:12])=[NH:33])[cH:34]1.O=[C:13](O)[c:14]1[cH:15][n:16][c:17]2[cH:18][cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([C:25]([F:26])([F:27])[F:28])[cH:29][cH:30]3)[cH:31][n:32]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][cH:8][c:9](-[c:10]2[n:11]... | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnc2ccc(-c3ccc(C(F)(F)F)cc3)cn12 | NS(=O)(=O)c1cccc(-c2noc(-c3cnc4ccc(-c5ccc(C(F)(F)F)cc5)cn34)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5ccccc5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5](:[c:6]):[#7;a:7]:1:[c:8].[NH;D1;+0:9]=[C;H0;D3;+0:10](-[NH;D2;+0:11]-[OH;D1;+0:12])-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:[c:17]>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:9]:[c;H0;D3;+0:10](-[c;H0;D3;+0:13](:[c:14]:[c:15]):[c:16]:... | null | [] | null | null | null | null | The title compound was prepared from 6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.35) (153 mg, 0.5 mmol) and N-hydroxy-3-sulfamoyl-benzamidine [CAS-No. 9000-88-7] (161 mg, 0.75 mmol) according to general procedure II. Obtained after trituration with water and further purification by ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1ccn2ccnc2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1cccc(S(N)(=O)=O)c1.O=C(O)c1cnc2ccc(-c3ccc(C(F)(F)F)cc3)cn12>>NS(=O)(=O)c1cccc(-c2noc(-c3cnc4ccc(-c5ccc(C(F)(F)F)cc5)cn34)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-89a9321c269c4b66a210c2dedb0f4aa7 | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnc2ccc(-c3ccc(C(F)(F)F)cc3)cn12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnc4ccc(-c5ccc(C(F)(F)F)cc5)cn34)n2)s1 | FC(C1=CC=C(C=C1)C=1C=CC=2N(C1)C(=CN2)C(=O)O)(F)F.ONC(=N)C=1SC(=CC1)S(N)(=O)=O>>FC(C1=CC=C(C=C1)C=1C=CC=2N(C1)C(=CN2)C2=NC(=NO2)C2=CC=C(S2)S(=O)(=O)N)(F)F | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:32])[s:33]1.O=[C:12](O)[c:13]1[cH:14][n:15][c:16]2[cH:17][cH:18][c:19](-[c:20]3[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28][cH:29]3)[cH:30][n:31]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][o:11][c:12](-[... | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnc2ccc(-c3ccc(C(F)(F)F)cc3)cn12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnc4ccc(-c5ccc(C(F)(F)F)cc5)cn34)n2)s1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5cccs5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5](:[c:6]):[#7;a:7]:1:[c:8].[NH;D1;+0:9]=[C;H0;D3;+0:10](-[NH;D2;+0:11]-[OH;D1;+0:12])-[c;H0;D3;+0:13]1:[#16;a:14]:[c:15]:[c:16]:[c:17]:1>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:9]:[c;H0;D3;+0:10](-[c;H0;D3;+0:13]3:[#16;a:14]:[c:15]... | null | [] | null | null | null | null | The title compound was prepared from 6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.35) (153 mg, 0.5 mmol) and N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) according to general procedure II. Obtained after trituration with water and further purifica... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccsc1.c1ncon1.c1ccn2ccnc2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnc2ccc(-c3ccc(C(F)(F)F)cc3)cn12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnc4ccc(-c5ccc(C(F)(F)F)cc5)cn34)n2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ac05e71e0574b0d8431b306c2e5db98 | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnc2ccc(-c3ccc(Cl)cc3)cn12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnc4ccc(-c5ccc(Cl)cc5)cn34)n2)s1 | ClC1=CC=C(C=C1)C=1C=CC=2N(C1)C(=CN2)C(=O)O.ONC(=N)C=1SC(=CC1)S(N)(=O)=O>>ClC1=CC=C(C=C1)C=1C=CC=2N(C1)C(=CN2)C2=NC(=NO2)C2=CC=C(S2)S(=O)(=O)N | [NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([NH:10][OH:11])=[NH:29])[s:30]1.O=[C:12](O)[c:13]1[cH:14][n:15][c:16]2[cH:17][cH:18][c:19](-[c:20]3[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]3)[cH:27][n:28]12>>[NH2:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[n:10][o:11][c:12](-[c:13]3[cH:14][n:15][c... | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnc2ccc(-c3ccc(Cl)cc3)cn12 | NS(=O)(=O)c1ccc(-c2noc(-c3cnc4ccc(-c5ccc(Cl)cc5)cn34)n2)s1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5cccs5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5](:[c:6]):[#7;a:7]:1:[c:8].[NH;D1;+0:9]=[C;H0;D3;+0:10](-[NH;D2;+0:11]-[OH;D1;+0:12])-[c;H0;D3;+0:13]1:[#16;a:14]:[c:15]:[c:16]:[c:17]:1>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:9]:[c;H0;D3;+0:10](-[c;H0;D3;+0:13]3:[#16;a:14]:[c:15]... | null | [] | null | null | null | null | The title compound was prepared from 6-(4-chloro-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.36) (136 mg, 0.5 mmol) and N-hydroxy-5-sulfamoyl-thiophene-2-carboxamidine (example B.2) (166 mg, 0.75 mmol) according to general procedure II. Obtained after trituration with water and further purification by c... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccsc1.c1ncon1.c1ccn2ccnc2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(S(N)(=O)=O)s1.O=C(O)c1cnc2ccc(-c3ccc(Cl)cc3)cn12>>NS(=O)(=O)c1ccc(-c2noc(-c3cnc4ccc(-c5ccc(Cl)cc5)cn34)n2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ff99612bc454e7a8ded31e1b1598abe | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnc2ccc(-c3ccc(C(F)(F)F)cc3)cn12>>Nc1ccc(-c2noc(-c3cnc4ccc(-c5ccc(C(F)(F)F)cc5)cn34)n2)cn1 | FC(C1=CC=C(C=C1)C=1C=CC=2N(C1)C(=CN2)C(=O)O)(F)F.NC1=NC=C(C(=N)NO)C=C1>>FC(C1=CC=C(C=C1)C=1C=CC=2N(C1)C(=CN2)C2=NC(=NO2)C=2C=CC(=NC2)N)(F)F | [NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:29])[cH:30][n:31]1.O=[C:9](O)[c:10]1[cH:11][n:12][c:13]2[cH:14][cH:15][c:16](-[c:17]3[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]3)[cH:27][n:28]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]3[cH:11][n:12][c:13]4[cH:14][cH:15][... | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnc2ccc(-c3ccc(C(F)(F)F)cc3)cn12 | Nc1ccc(-c2noc(-c3cnc4ccc(-c5ccc(C(F)(F)F)cc5)cn34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5cccnc5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5](:[c:6]):[#7;a:7]:1:[c:8].[NH;D1;+0:9]=[C;H0;D3;+0:10](-[NH;D2;+0:11]-[OH;D1;+0:12])-[c;H0;D3;+0:13]1:[c:14]:[#7;a:15]:[c:16]:[c:17]:[c:18]:1>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:9]:[c;H0;D3;+0:10](-[c;H0;D3;+0:13]3:[c:14]:[#7;... | null | [] | null | null | null | null | The title compound was prepared from 6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.35) (153 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on silica gel (ethyl acetate) and fur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1ccn2ccnc2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnc2ccc(-c3ccc(C(F)(F)F)cc3)cn12>>Nc1ccc(-c2noc(-c3cnc4ccc(-c5ccc(C(F)(F)F)cc5)cn34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-299582bf110b4d99ae027a09c3140f65 | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnc2ccc(-c3ccc(Cl)cc3)cn12>>Nc1ccc(-c2noc(-c3cnc4ccc(-c5ccc(Cl)cc5)cn34)n2)cn1 | ClC1=CC=C(C=C1)C=1C=CC=2N(C1)C(=CN2)C(=O)O.NC1=NC=C(C(=N)NO)C=C1>>ClC1=CC=C(C=C1)C=1C=CC=2N(C1)C(=CN2)C2=NC(=NO2)C=2C=CC(=NC2)N | [NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:26])[cH:27][n:28]1.O=[C:9](O)[c:10]1[cH:11][n:12][c:13]2[cH:14][cH:15][c:16](-[c:17]3[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]3)[cH:24][n:25]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]3[cH:11][n:12][c:13]4[cH:14][cH:15][c:16](-[c:17]5[cH:18]... | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnc2ccc(-c3ccc(Cl)cc3)cn12 | Nc1ccc(-c2noc(-c3cnc4ccc(-c5ccc(Cl)cc5)cn34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5cccnc5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5](:[c:6]):[#7;a:7]:1:[c:8].[NH;D1;+0:9]=[C;H0;D3;+0:10](-[NH;D2;+0:11]-[OH;D1;+0:12])-[c;H0;D3;+0:13]1:[c:14]:[#7;a:15]:[c:16]:[c:17]:[c:18]:1>>[c:6]:[c:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:9]:[c;H0;D3;+0:10](-[c;H0;D3;+0:13]3:[c:14]:[#7;... | null | [] | null | null | null | null | The title compound was prepared from 6-(4-chloro-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.36) (136 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on silica gel (ethyl acetate) and further puri... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1ccn2ccnc2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnc2ccc(-c3ccc(Cl)cc3)cn12>>Nc1ccc(-c2noc(-c3cnc4ccc(-c5ccc(Cl)cc5)cn34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-85e64ef14bca46be9a99aaf30ff3bb40 | N=C(NO)c1ccnc(N)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>Nc1cc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)ccn1 | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC=C(C=C2)C(F)(F)F)(F)F.NC1=NC=CC(=C1)C(=N)NO>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C2=CC(=NC=C2)N)C2=CC=C(C=C2)C(F)(F)F)(F)F | [NH2:1][c:2]1[cH:3][c:4]([C:5]([NH:6][OH:7])=[NH:32])[cH:33][cH:34][n:35]1.O=[C:8](O)[c:9]1[cH:10][n:11][n:12]2[c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][c:19](-[c:20]3[cH:21][cH:22][c:23]([C:24]([F:25])([F:26])[F:27])[cH:28][cH:29]3)[n:30][c:31]12>>[NH2:1][c:2]1[cH:3][c:4](-[c:5]2[n:6][o:7][c:8](-[c:9]3[cH:10][n:11][... | N=C(NO)c1ccnc(N)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12 | Nc1cc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)ccn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5ccncc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[N;D1;H2:10]-[c:11]1:[#7;a:12]:[c:13]:[c:14]:[c;H0;D3;+0:15](-[C;H0;D3;+0:16](=[NH;D1;+0:17])-[NH;D2;+0:18]-[OH;D1;+0:19]):[c:20]:1>>[N;D1;H2:10]-[c:11]1:[#7;a:12]:[c:13]:[c:14]:[c;H0;D3;+0:15](-[c;H0;D3;+0:16]2:[n;H0;D2;+0:17]:... | null | [] | null | null | null | null | The title compound was prepared from 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.2) (188 mg, 0.5 mmol) and 2-amino-N-hydroxy-pyridine-4-carboxamidine (example B.6) (114 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chroma... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccnc(N)c1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(C(F)(F)F)cc3)nc12>>Nc1cc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(C(F)(F)F)cc5)nc34)n2)ccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-65d57abd81b542efab6bff899157fba9 | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccnc(N)c1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4ccnc(N)c4)no3)cnc12 | CC=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C(=O)O.NC1=NC=CC(=C1)C(=N)NO>>CC=1C=2N(C=C(C1)C1=CC=C(C=C1)C(F)(F)F)C(=CN2)C2=NC(=NO2)C2=CC(=NC=C2)N | O=[C:18](O)[c:17]1[n:16]2[cH:15][c:4](-[c:5]3[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH:14]3)[cH:3][c:2]([CH3:1])[c:32]2[n:31][cH:30]1.[NH:19]=[C:20]([c:21]1[cH:22][cH:23][n:24][c:25]([NH2:26])[cH:27]1)[NH:28][OH:29]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([C:9]([F:10])([F:11])[F:12])[cH:13][cH... | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccnc(N)c1 | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4ccnc(N)c4)no3)cnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5ccncc5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5]:[#7;a:6]:1:[c:7].[N;D1;H2:8]-[c:9]1:[#7;a:10]:[c:11]:[c:12]:[c;H0;D3;+0:13](-[C;H0;D3;+0:14](=[NH;D1;+0:15])-[NH;D2;+0:16]-[OH;D1;+0:17]):[c:18]:1>>[N;D1;H2:8]-[c:9]1:[#7;a:10]:[c:11]:[c:12]:[c;H0;D3;+0:13](-[c;H0;D3;+0:14]2:[n;H0;D2;+0:15]:[c;H0;D3;+0:1](-[c;H0... | null | [] | null | null | null | null | The title compound was prepared from 8-methyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.34) (160 mg, 0.5 mmol) and 2-amino-N-hydroxy-pyridine-4-carboxamidine (example B.6) (114 mg, 0.75 mmol) according to general procedure II. Obtained after purification by flash chromatography on... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1.c1ccncc1.c1ccn2ccnc2c1 | HO- | null | null | null | Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(C(=O)O)cnc12.N=C(NO)c1ccnc(N)c1>>Cc1cc(-c2ccc(C(F)(F)F)cc2)cn2c(-c3nc(-c4ccnc(N)c4)no3)cnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cf3aa0cf7032436eaeec0836fe4291f5 | N=C(NO)c1ccnc(N)c1.O=C(O)c1cnc2ccc(-c3ccc(C(F)(F)F)cc3)cn12>>Nc1cc(-c2noc(-c3cnc4ccc(-c5ccc(C(F)(F)F)cc5)cn34)n2)ccn1 | FC(C1=CC=C(C=C1)C=1C=CC=2N(C1)C(=CN2)C(=O)O)(F)F.NC1=NC=CC(=C1)C(=N)NO>>FC(C1=CC=C(C=C1)C=1C=CC=2N(C1)C(=CN2)C2=NC(=NO2)C2=CC(=NC=C2)N)(F)F | [NH2:1][c:2]1[cH:3][c:4]([C:5]([NH:6][OH:7])=[NH:28])[cH:29][cH:30][n:31]1.O=[C:8](O)[c:9]1[cH:10][n:11][c:12]2[cH:13][cH:14][c:15](-[c:16]3[cH:17][cH:18][c:19]([C:20]([F:21])([F:22])[F:23])[cH:24][cH:25]3)[cH:26][n:27]12>>[NH2:1][c:2]1[cH:3][c:4](-[c:5]2[n:6][o:7][c:8](-[c:9]3[cH:10][n:11][c:12]4[cH:13][cH:14][c:15](-... | N=C(NO)c1ccnc(N)c1.O=C(O)c1cnc2ccc(-c3ccc(C(F)(F)F)cc3)cn12 | Nc1cc(-c2noc(-c3cnc4ccc(-c5ccc(C(F)(F)F)cc5)cn34)n2)ccn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccc3ncc(-c4nc(-c5ccncc5)no4)n3c2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[c:5](:[c:6]):[#7;a:7]:1:[c:8].[N;D1;H2:9]-[c:10]1:[#7;a:11]:[c:12]:[c:13]:[c;H0;D3;+0:14](-[C;H0;D3;+0:15](=[NH;D1;+0:16])-[NH;D2;+0:17]-[OH;D1;+0:18]):[c:19]:1>>[N;D1;H2:9]-[c:10]1:[#7;a:11]:[c:12]:[c:13]:[c;H0;D3;+0:14](-[c;H0;D3;+0:15]2:[n;H0;D2;+0:16]:[c;H0;D3;+0... | null | [] | null | null | null | null | The title compound was prepared from 6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-3-carboxylic acid (example C.35) (153 mg, 0.5 mmol) and 2-amino-N-hydroxy-pyridine-4-carboxamidine (example B.6) (114 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromatography on silica ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1ccn2ccnc2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccnc(N)c1.O=C(O)c1cnc2ccc(-c3ccc(C(F)(F)F)cc3)cn12>>Nc1cc(-c2noc(-c3cnc4ccc(-c5ccc(C(F)(F)F)cc5)cn34)n2)ccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4c6e241f6ee14d74add617a0bffee30d | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)cn1 | ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.NC1=NC=C(C(=N)NO)C=C1>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N | [NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:30])[cH:31][n:32]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][c:20](-[c:21]3[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]3)[n:28][c:29]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]3[cH:11][n:12][n:13]4[c:14]([... | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12 | Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[c:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.4) (171 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on silica gel (ethyl aceta... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)(F)F)cc(-c3ccc(Cl)cc3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cac88422da5a4614a6bbc24edcfaffd2 | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(Cl)cc3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)cn1 | ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)F)N=CC2C(=O)O.NC1=NC=C(C(=N)NO)C=C1>>ClC1=CC=C(C=C1)C1=NC=2N(C(=C1)C(F)F)N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N | [NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:29])[cH:30][n:31]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([CH:15]([F:16])[F:17])[cH:18][c:19](-[c:20]3[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]3)[n:27][c:28]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]3[cH:11][n:12][n:13]4[c:14]([CH:15](... | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(Cl)cc3)nc12 | Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[c:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-phenyl)-7-difluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.3) (162 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on silica gel (ethyl acetat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(Cl)cc3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(Cl)cc5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a206f3f80d924609a735398bedca2cc2 | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1Cl.N=C(NO)c1ccc(N)nc1>>Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1Cl | ClC1=C(C=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O)C.NC1=NC=C(C(=N)NO)C=C1>>ClC1=C(C=C(C=C1)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N)C | O=[C:16](O)[c:15]1[cH:14][n:13][n:12]2[c:7]([C:8]([F:9])([F:10])[F:11])[cH:6][c:5](-[c:4]3[cH:3][c:2]([CH3:1])[c:32]([Cl:33])[cH:31][cH:30]3)[n:29][c:28]21.[NH:17]=[C:18]([c:19]1[cH:20][cH:21][c:22]([NH2:23])[n:24][cH:25]1)[NH:26][OH:27]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[n:12]3[n:... | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1Cl.N=C(NO)c1ccc(N)nc1 | Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1Cl | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[c:16]:[c:17]:[#7;a:18]:[c:19]:1>>[c:9]:[#7;a:8]:[c:7]1:[#7;a:5](:[c:6]):[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c;H0;D... | null | [] | null | null | null | null | The title compound was prepared from 5-(4-chloro-3-methyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.6) (178 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on silica gel (et... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1cnc2ccnn2c1.c1ncon1.c1ccncc1 | HO- | null | null | null | Cc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1Cl.N=C(NO)c1ccc(N)nc1>>Cc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ece272c803614b74bd41b0cf9d36bd4c | Cc1cc(-c2cc(C(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(N)nc1>>Cc1cc(-c2cc(C(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1C(F)(F)F | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC(=C(C=C2)C(F)(F)F)C)F.NC1=NC=C(C(=N)NO)C=C1>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N)C2=CC(=C(C=C2)C(F)(F)F)C)F | O=[C:15](O)[c:14]1[cH:13][n:12][n:11]2[c:7]([CH:8]([F:9])[F:10])[cH:6][c:5](-[c:4]3[cH:3][c:2]([CH3:1])[c:31]([C:32]([F:33])([F:34])[F:35])[cH:30][cH:29]3)[n:28][c:27]21.[NH:16]=[C:17]([c:18]1[cH:19][cH:20][c:21]([NH2:22])[n:23][cH:24]1)[NH:25][OH:26]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([CH:8]([F:9])[F:10])[n:... | Cc1cc(-c2cc(C(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(N)nc1 | Cc1cc(-c2cc(C(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1C(F)(F)F | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[c:16]:[c:17]:[#7;a:18]:[c:19]:1>>[c:9]:[#7;a:8]:[c:7]1:[#7;a:5](:[c:6]):[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c;H0;D... | null | [] | null | null | null | null | The title compound was prepared from 7-difluoromethyl-5-(3-methyl-4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.5) (186 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on silica... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1cnc2ccnn2c1.c1ncon1.c1ccncc1 | HO- | null | null | null | Cc1cc(-c2cc(C(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(N)nc1>>Cc1cc(-c2cc(C(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-00022d89cfdb478fa429ab6769eadcc0 | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(Cl)c(Cl)c3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(Cl)c(Cl)c5)nc34)n2)cn1 | ClC=1C=C(C=CC1Cl)C1=NC=2N(C(=C1)C(F)F)N=CC2C(=O)O.NC1=NC=C(C(=N)NO)C=C1>>ClC=1C=C(C=CC1Cl)C1=NC=2N(C(=C1)C(F)F)N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N | [NH2:1][c:2]1[cH:3][cH:4][c:5]([C:6]([NH:7][OH:8])=[NH:30])[cH:31][n:32]1.O=[C:9](O)[c:10]1[cH:11][n:12][n:13]2[c:14]([CH:15]([F:16])[F:17])[cH:18][c:19](-[c:20]3[cH:21][cH:22][c:23]([Cl:24])[c:25]([Cl:26])[cH:27]3)[n:28][c:29]12>>[NH2:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][o:8][c:9](-[c:10]3[cH:11][n:12][n:13]4[c:14](... | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(Cl)c(Cl)c3)nc12 | Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(Cl)c(Cl)c5)nc34)n2)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[#7;a:16]:[c:17]:[c:18]:[c:19]:1>>[c:6]:[#7;a:5]1:[#7;a:4]:[c:3]:[c;H0;D3;+0:2](-[c;H0;D3;+0:1]2:[n;H0;D2;+0:10]:[c;H0;D3;+0:11](-[c;H0;D3;+0:14... | null | [] | null | null | null | null | The title compound was prepared from 5-(3,4-dichloro-phenyl)-7-difluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.7) (179 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on silica gel (ethyl ac... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccncc1.c1ncon1.c1cnc2ccnn2c1.c1ccccc1 | HO- | null | null | null | N=C(NO)c1ccc(N)nc1.O=C(O)c1cnn2c(C(F)F)cc(-c3ccc(Cl)c(Cl)c3)nc12>>Nc1ccc(-c2noc(-c3cnn4c(C(F)F)cc(-c5ccc(Cl)c(Cl)c5)nc34)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ced392d6c4b4782937e781291ddf229 | CCOc1cc(-c2cc(C(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(N)nc1>>CCOc1cc(-c2cc(C(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1C(F)(F)F | FC(C1=CC(=NC=2N1N=CC2C(=O)O)C2=CC(=C(C=C2)C(F)(F)F)OCC)F.NC1=NC=C(C(=N)NO)C=C1>>FC(C1=CC(=NC=2N1N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N)C2=CC(=C(C=C2)C(F)(F)F)OCC)F | O=[C:17](O)[c:16]1[cH:15][n:14][n:13]2[c:9]([CH:10]([F:11])[F:12])[cH:8][c:7](-[c:6]3[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:33]([C:34]([F:35])([F:36])[F:37])[cH:32][cH:31]3)[n:30][c:29]21.[NH:18]=[C:19]([c:20]1[cH:21][cH:22][c:23]([NH2:24])[n:25][cH:26]1)[NH:27][OH:28]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:... | CCOc1cc(-c2cc(C(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(N)nc1 | CCOc1cc(-c2cc(C(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1C(F)(F)F | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[c:16]:[c:17]:[#7;a:18]:[c:19]:1>>[c:9]:[#7;a:8]:[c:7]1:[#7;a:5](:[c:6]):[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c;H0;D... | null | [] | null | null | null | null | The title compound was prepared from 7-difluoromethyl-5-(3-ethoxy-4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.12) (201 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on silic... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1cnc2ccnn2c1.c1ncon1.c1ccncc1 | HO- | null | null | null | CCOc1cc(-c2cc(C(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(N)nc1>>CCOc1cc(-c2cc(C(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a6b50ee1d9984c05a1df25f3a0319baf | CCOc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(N)nc1>>CCOc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1C(F)(F)F | C(C)OC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C(=O)O.NC1=NC=C(C(=N)NO)C=C1>>C(C)OC=1C=C(C=CC1C(F)(F)F)C1=NC=2N(C(=C1)C(F)(F)F)N=CC2C2=NC(=NO2)C=2C=CC(=NC2)N | O=[C:18](O)[c:17]1[cH:16][n:15][n:14]2[c:9]([C:10]([F:11])([F:12])[F:13])[cH:8][c:7](-[c:6]3[cH:5][c:4]([O:3][CH2:2][CH3:1])[c:34]([C:35]([F:36])([F:37])[F:38])[cH:33][cH:32]3)[n:31][c:30]21.[NH:19]=[C:20]([c:21]1[cH:22][cH:23][c:24]([NH2:25])[n:26][cH:27]1)[NH:28][OH:29]>>[CH3:1][CH2:2][O:3][c:4]1[cH:5][c:6](-[c:7]2[c... | CCOc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(N)nc1 | CCOc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1C(F)(F)F | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 2705d90bec25fbfd90e98961543fc48076d6c6e89a60f6012587bc2b1ce04b13 | 7a7b5724a99f7b1ff61b1937894d90e5ffd70f2e3f6ae2fa59809f82d476dd48 | c1ccc(-c2ccn3ncc(-c4nc(-c5cccnc5)no4)c3n2)cc1 | O-[C;H0;D3;+0:1](=O)-[c;H0;D3;+0:2]1:[c:3]:[#7;a:4]:[#7;a:5](:[c:6]):[c:7]:1:[#7;a:8]:[c:9].[NH;D1;+0:10]=[C;H0;D3;+0:11](-[NH;D2;+0:12]-[OH;D1;+0:13])-[c;H0;D3;+0:14]1:[c:15]:[c:16]:[c:17]:[#7;a:18]:[c:19]:1>>[c:9]:[#7;a:8]:[c:7]1:[#7;a:5](:[c:6]):[#7;a:4]:[c:3]:[c;H0;D3;+0:2]:1-[c;H0;D3;+0:1]1:[n;H0;D2;+0:10]:[c;H0;D... | null | [] | null | null | null | null | The title compound was prepared from 5-(3-ethoxy-4-trifluoromethyl-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.11) (210 mg, 0.5 mmol) and 6-amino-N-hydroxy-nicotinamidine (example B.4) (114 mg, 0.75 mmol) according to general procedure II. Obtained after flash chromatography on sili... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | null | null | c1ncon1 | c1ccccc1.c1cnc2ccnn2c1.c1ncon1.c1ccncc1 | HO- | null | null | null | CCOc1cc(-c2cc(C(F)(F)F)n3ncc(C(=O)O)c3n2)ccc1C(F)(F)F.N=C(NO)c1ccc(N)nc1>>CCOc1cc(-c2cc(C(F)(F)F)n3ncc(-c4nc(-c5ccc(N)nc5)no4)c3n2)ccc1C(F)(F)F |
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