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-5f9ae00d60e145d8aec04edc69a01edb | C=CC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccc(OC)cc1.CCC(N=C=O)c1ccccc1>>C=CC[C@H]1C(=O)N(C(=O)NC(CC)c2ccccc2)[C@@H]1C(=O)OCc1ccc(OC)cc1 | COC1=CC=C(COC(=O)[C@H]2NC([C@@H]2CC=C)=O)C=C1.C(C)N(CC)CC.C(C)C(C1=CC=CC=C1)N=C=O>>COC1=CC=C(COC(=O)[C@H]2N(C([C@@H]2CC=C)=O)C(NC(CC)C2=CC=CC=C2)=O)C=C1 | [CH2:1]=[CH:2][CH2:3][C@H:4]1[C:5](=[O:6])[NH:7][C@@H:20]1[C:21](=[O:22])[O:23][CH2:24][c:25]1[cH:26][cH:27][c:28]([O:29][CH3:30])[cH:31][cH:32]1.[C:8](=[O:9])=[N:10][CH:11]([CH2:12][CH3:13])[c:14]1[cH:15][cH:16][cH:17][cH:18][cH:19]1>>[CH2:1]=[CH:2][CH2:3][C@H:4]1[C:5](=[O:6])[N:7]([C:8](=[O:9])[NH:10][CH:11]([CH2:12]... | C=CC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccc(OC)cc1.CCC(N=C=O)c1ccccc1 | C=CC[C@H]1C(=O)N(C(=O)NC(CC)c2ccccc2)[C@@H]1C(=O)OCc1ccc(OC)cc1 | null | null | C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 105e9b64246d79f0e1854bc5e41627c9f514c23def37bcfaadf185ae4d2249f3 | d8031df9745ffb9494a0da2553ed47ba21f8143926e9537ff85149a4ef4cadb4 | O=C(OCc1ccccc1)[C@@H]1CC(=O)N1C(=O)NCc1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]1-[C:6]-[C:7](=[O;D1;H0:8])-[NH;D2;+0:9]-1.[C:10]-[C:11](-[c:12])-[N;H0;D2;+0:13]=[C;H0;D2;+0:14]=[O;D1;H0:15]>>[C:10]-[C:11](-[c:12])-[NH;D2;+0:13]-[C;H0;D3;+0:14](=[O;D1;H0:15])-[N;H0;D3;+0:9]1-[C:5](-[C:3](=[O;D1;H0:4])-[#8:2]-[C:1])-[C:6]-[C:7]-1=[O;D1;H0:8] | 59 | [{"value": 59.0, "product": "COC1=CC=C(COC(=O)[C@H]2N(C([C@@H]2CC=C)=O)C(NC(CC)C2=CC=CC=C2)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.3, "product": "COC1=CC=C(COC(=O)[C@H]2N(C([C@@H]2CC=C)=O)C(NC(CC)C2=CC=CC=C2)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of compound 59 (41 mg, 0.15 mmol), triethylamine (83 uL, 0.60 mmol), α-ethyl-benzyl isocyanate (29 mg, 0.18 mmol) in methylene chloride (1.2 mL) was stirred overnight. TLC analysis indicated the completion the reaction. Removal of solvents gave the crude material, which was purified by preparative TLC plate (... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amide | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | 8 | C=CC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccc(OC)cc1.CCC(N=C=O)c1ccccc1>C(Cl)Cl>C=CC[C@H]1C(=O)N(C(=O)NC(CC)c2ccccc2)[C@@H]1C(=O)OCc1ccc(OC)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-77acb199190646b69d5bf45a17acfef3 | C=CC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccc(OC)cc1.OB(O)c1ccccn1>>C=CCC1C(=O)N(c2ccccn2)C1C(=O)OCc1ccc(OC)cc1 | COC1=CC=C(COC(=O)[C@H]2NC([C@@H]2CC=C)=O)C=C1.N1=C(C=CC=C1)B(O)O.C(C)N(CC)CC>>COC1=CC=C(COC(=O)C2N(C(C2CC=C)=O)C2=NC=CC=C2)C=C1 | [CH2:1]=[CH:2][CH2:3][C@H:4]1[C:5](=[O:6])[NH:7][C@@H:14]1[C:15](=[O:16])[O:17][CH2:18][c:19]1[cH:20][cH:21][c:22]([O:23][CH3:24])[cH:25][cH:26]1.OB(O)[c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1>>[CH2:1]=[CH:2][CH2:3][CH:4]1[C:5](=[O:6])[N:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[CH:14]1[C:15](=[O:16])[O:17][CH2:18][c... | C=CC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccc(OC)cc1.OB(O)c1ccccn1 | C=CCC1C(=O)N(c2ccccn2)C1C(=O)OCc1ccc(OC)cc1 | null | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-] | ClCCl | Heteroatom Alkylation and Arylation | Petasis reaction with amines and boronic acids | 6dc8be6683fc000f47836cb0825129f9806bea69e54e5f36d246f067c7e375be | d8988f95994c3a53b8581714df91fdcf58fce7c875a9f3af0fd1011694639d17 | O=C(OCc1ccccc1)C1CC(=O)N1c1ccccn1 | O-B(-O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C@H;D3;+0:10]1-[NH;D2;+0:11]-[C:12](=[O;D1;H0:13])-[C:14]-1-[C:15]-[C:16]=[C;D1;H2:17]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10]1-[C:14](-[C:15]-[C:16]=[C;D1;H2:17])-[C:12](=[O;D1;H0:13])-[N;H0;D3;+0:11]-1-[c;H0;D3;+0:1](:[#7;a:... | 24.8 | [{"value": 20.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.8, "product": "COC1=CC=C(COC(=O)C2N(C(C2CC=C)=O)C2=NC=CC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.8, "product": "COC1=CC=C(COC(=O)C2N(C(C2CC=C)=O)C2=NC=CC=C2)C=C1", "details": "CALCULATEDPERCEN... | null | null | 2 | DAY | A mixture of β-lactam 59 (60 mg, 0.22 mmol), Pyridin-2-boronic acid (81 mg, 0.66 mmol), copper acetate (120 mg, 0.66 mmol), triethylamine (0.153 mL, 1.1 mmol) and activated 4A molecular sieves (270 mg) in dichloromethane (5 mL) was stirred at room temperature for 2 days. The reaction mixture was filtered through celite... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Boronic acid | Tertiary amide | C1CNC1.c1ccncc1 | C1C[NH]C1.c1ccncc1 | C1C[NH]C1.c1ccncc1.c1ccccc1 | HO-.B | C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].ClCCl | null | 48 | C=CC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccc(OC)cc1.OB(O)c1ccccn1>C(C)(=O)[O-].[Cu+2].C(C)(=O)[O-].ClCCl>C=CCC1C(=O)N(c2ccccn2)C1C(=O)OCc1ccc(OC)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7572a4c322e0451fab264ba5f3042b63 | COc1ccc(C[C@@]2(C(=O)[O-])[C@@H](CC=NNC(=N)N)C(=O)N2c2ccccn2)cc1>>N=C(N)NN=CC[C@H]1C(=O)N(c2ccccn2)[C@@H]1C(=O)O | COC1=CC=C(C[C@@]2(N(C([C@@H]2CC=NNC(=N)N)=O)C2=NC=CC=C2)C(=O)[O-])C=C1.C(=O)(C(F)(F)F)O.C(Cl)Cl>>N(C(=N)N)N=CC[C@@H]1[C@H](N(C1=O)C1=NC=CC=C1)C(=O)O | COc1ccc(C[C@@:18]2([C:19](=[O:20])[O-:21])[C@@H:8]([CH2:7][CH:6]=[N:5][NH:4][C:2](=[NH:1])[NH2:3])[C:9](=[O:10])[N:11]2[c:12]2[cH:13][cH:14][cH:15][cH:16][n:17]2)cc1>>[NH:1]=[C:2]([NH2:3])[NH:4][N:5]=[CH:6][CH2:7][C@H:8]1[C:9](=[O:10])[N:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][n:17]2)[C@@H:18]1[C:19](=[O:20])[OH:21] | COc1ccc(C[C@@]2(C(=O)[O-])[C@@H](CC=NNC(=N)N)C(=O)N2c2ccccn2)cc1 | N=C(N)NN=CC[C@H]1C(=O)N(c2ccccn2)[C@@H]1C(=O)O | null | null | null | Reduction | OtherReaction | 91a35220a001afa8ff2ec41d65d5a9d2e3cfc41128dc963de50b8f267a20d0f4 | fc36b78de76f2c5141892df769222d9a793f25ecdae731308a2cae6bc6b43b17 | O=C1CCN1c1ccccn1 | C-O-c1:c:c:c(-C-[C@;H0;D4;+0:1]2(-[C:2](-[O-;H0;D1:3])=[O;D1;H0:4])-[#7:5](-[c:6]:[#7;a:7])-[C:8](=[O;D1;H0:9])-[C:10]-2-[C:11]):c:c:1>>[#7;a:7]:[c:6]-[#7:5]1-[C:8](=[O;D1;H0:9])-[C:10](-[C:11])-[C@H;D3;+0:1]-1-[C:2](=[O;D1;H0:4])-[OH;D1;+0:3] | null | [] | null | null | null | null | The crude ester 82 was treated with TFA/DCM (0.75 mL/1 mL). After one and half hours, LC-MS analysis indicated completion of the reaction. The solvent was removed and the residue was purified by preparative HPLC (Vydac reverse phase C-18 column, 22×250 mm ID). Mobil phase: A=0.1% TFA in water, B=0.1% TFA in acetonitril... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Carboxylic acid | c1ccccc1.C1C[NH]C1 | C1C[NH]C1 | C1C[NH]C1.c1ccncc1 | HO- | null | null | null | COc1ccc(C[C@@]2(C(=O)[O-])[C@@H](CC=NNC(=N)N)C(=O)N2c2ccccn2)cc1>>N=C(N)NN=CC[C@H]1C(=O)N(c2ccccn2)[C@@H]1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eae34b8aaceb4b5d8843a897d73f8237 | CCOC(=O)[C@@H]1[C@@H](Sc2cccc([N+](=O)[O-])c2)C(=O)N1C(=O)N[C@H](C)c1ccccc1>>CCOC(=O)[C@@H]1[C@@H](Sc2cccc(N)c2)C(=O)N1C(=O)N[C@H](C)c1ccccc1 | C1(=CC=CC=C1)[C@@H](C)NC(=O)N1[C@@H]([C@H](C1=O)SC1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC.O.[Sn](Cl)(Cl)(Cl)Cl>>C1(=CC=CC=C1)[C@@H](C)NC(=O)N1[C@@H]([C@H](C1=O)SC1=CC(=CC=C1)N)C(=O)OCC | O=[N+:14]([O-])[c:13]1[cH:12][cH:11][cH:10][c:9]([S:8][C@@H:7]2[C@@H:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[N:18]([C:19](=[O:20])[NH:21][C@H:22]([CH3:23])[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[C:16]2=[O:17])[cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[C@@H:7]([S:8][c:9]2[cH:10][cH:11][cH:12][c:13]([NH2:14])[... | CCOC(=O)[C@@H]1[C@@H](Sc2cccc([N+](=O)[O-])c2)C(=O)N1C(=O)N[C@H](C)c1ccccc1 | CCOC(=O)[C@@H]1[C@@H](Sc2cccc(N)c2)C(=O)N1C(=O)N[C@H](C)c1ccccc1 | null | null | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(NCc1ccccc1)N1C[C@@H](Sc2ccccc2)C1=O | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 72 | [{"value": 72.0, "product": "C1(=CC=CC=C1)[C@@H](C)NC(=O)N1[C@@H]([C@H](C1=O)SC1=CC(=CC=C1)N)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.8, "product": "C1(=CC=CC=C1)[C@@H](C)NC(=O)N1[C@@H]([C@H](C1=O)SC1=CC(=CC=C1)N)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a solution of compound 85a (18 mg, 41 umol) in ethyl acetate (1 mL) was added tin chloride monohydrate (2.5 eq.) and the solution was heated to 50° C. After 1 h the solution was concentrated in vacuo. The residue was purified by column chromatography using a gradient of hexane/ethyl acetate 20-100% as eluent to yiel... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]C1.c1ccccc1.c1ccccc1 | Other | C(C)(=O)OCC | 50 | null | CCOC(=O)[C@@H]1[C@@H](Sc2cccc([N+](=O)[O-])c2)C(=O)N1C(=O)N[C@H](C)c1ccccc1>C(C)(=O)OCC>CCOC(=O)[C@@H]1[C@@H](Sc2cccc(N)c2)C(=O)N1C(=O)N[C@H](C)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5d6c32b8f5b147cb88587a2f071078f4 | CCOC(=O)[C@@H]1[C@H](Sc2cccc([N+](=O)[O-])c2)C(=O)N1C(=O)N[C@H](C)c1ccccc1>>CCOC(=O)[C@@H]1[C@H](Sc2cccc(N)c2)C(=O)N1C(=O)N[C@H](C)c1ccccc1 | C1(=CC=CC=C1)[C@@H](C)NC(=O)N1[C@@H]([C@@H](C1=O)SC1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC.O.[Sn](Cl)(Cl)(Cl)Cl>>C1(=CC=CC=C1)[C@@H](C)NC(=O)N1[C@@H]([C@@H](C1=O)SC1=CC(=CC=C1)N)C(=O)OCC | O=[N+:14]([O-])[c:13]1[cH:12][cH:11][cH:10][c:9]([S:8][C@H:7]2[C@@H:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[N:18]([C:19](=[O:20])[NH:21][C@H:22]([CH3:23])[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[C:16]2=[O:17])[cH:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[C@H:7]([S:8][c:9]2[cH:10][cH:11][cH:12][c:13]([NH2:14])[cH... | CCOC(=O)[C@@H]1[C@H](Sc2cccc([N+](=O)[O-])c2)C(=O)N1C(=O)N[C@H](C)c1ccccc1 | CCOC(=O)[C@@H]1[C@H](Sc2cccc(N)c2)C(=O)N1C(=O)N[C@H](C)c1ccccc1 | null | null | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(NCc1ccccc1)N1C[C@H](Sc2ccccc2)C1=O | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 63.6 | [{"value": 63.0, "product": "C1(=CC=CC=C1)[C@@H](C)NC(=O)N1[C@@H]([C@@H](C1=O)SC1=CC(=CC=C1)N)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.6, "product": "C1(=CC=CC=C1)[C@@H](C)NC(=O)N1[C@@H]([C@@H](C1=O)SC1=CC(=CC=C1)N)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | null | null | To a solution of 85b (17 mg, 38 umol) in ethyl acetate (1 mL) at room temperature was added tin chloride monohydrate (2.5 eq.) and the solution was heated to 50° C. After 1 h the solution was concentrated in vacuo. The residue was purified by column chromatography using a gradient of hexane/ethyl acetate 20-100% as elu... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | C1C[NH]C1.c1ccccc1.c1ccccc1 | Other | C(C)(=O)OCC | 50 | null | CCOC(=O)[C@@H]1[C@H](Sc2cccc([N+](=O)[O-])c2)C(=O)N1C(=O)N[C@H](C)c1ccccc1>C(C)(=O)OCC>CCOC(=O)[C@@H]1[C@H](Sc2cccc(N)c2)C(=O)N1C(=O)N[C@H](C)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4050746a657246f083fa41a02d1b514e | C[C@@H](NC(=O)N1C(=O)[C@H](Cc2ccnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c2)[C@H]1C(=O)NS(C)(=O)=O)c1ccccc1>>C[C@@H](NC(=O)N1C(=O)[C@H](Cc2ccnc(N)c2)[C@H]1C(=O)NS(C)(=O)=O)c1ccccc1 | C(C)(C)(C)OC(=O)N(C1=NC=CC(=C1)C[C@@H]1[C@H](N(C1=O)C(=O)N[C@H](C)C1=CC=CC=C1)C(=O)NS(=O)(=O)C)C(=O)OC(C)(C)C.C(=O)(C(F)(F)F)O>>NC1=NC=CC(=C1)C[C@@H]1[C@H](N(C1=O)C(=O)N[C@H](C)C1=CC=CC=C1)C(=O)NS(=O)(=O)C | CC(C)(C)OC(=O)[N:16](C(=O)OC(C)(C)C)[c:15]1[n:14][cH:13][cH:12][c:11]([CH2:10][C@H:9]2[C:7](=[O:8])[N:6]([C:4]([NH:3][C@H:2]([CH3:1])[c:26]3[cH:27][cH:28][cH:29][cH:30][cH:31]3)=[O:5])[C@@H:18]2[C:19](=[O:20])[NH:21][S:22]([CH3:23])(=[O:24])=[O:25])[cH:17]1>>[CH3:1][C@@H:2]([NH:3][C:4](=[O:5])[N:6]1[C:7](=[O:8])[C@H:9]... | C[C@@H](NC(=O)N1C(=O)[C@H](Cc2ccnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c2)[C@H]1C(=O)NS(C)(=O)=O)c1ccccc1 | C[C@@H](NC(=O)N1C(=O)[C@H](Cc2ccnc(N)c2)[C@H]1C(=O)NS(C)(=O)=O)c1ccccc1 | null | null | ClCCl | Reduction | Boc amine deprotection | f552418eb10f74be275b3d2d2e4940118153e34a0e9e4737d38c7264f73cdda0 | c2e7125d1a630bb54d8f171aedbfa925f5104f1c1e5ac8c4ed9643a0c1117a44 | O=C(NCc1ccccc1)N1C[C@@H](Cc2ccncc2)C1=O | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-C(=O)-O-C(-C)(-C)-C)-[c:2](:[c:3]):[#7;a:4]:[c:5]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | 1 | HOUR | To a solution of 95 in 1 mL dichloromethane was added 300 uL of TFA. The reaction was stirred for 1 hour and then concentrated in vacuo. The crude material was purified via reverse phase HPLC (C18, acetonitrile/water with 0.1% TFA) to yield 0.75 mg of 96. MS [M+H]+=446.0
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Substituted dicarboximide.Boc.Boc | Primary amine | null | null | C1C[NH]C1.c1ccncc1.c1ccccc1 | HO- | ClCCl | null | 1 | C[C@@H](NC(=O)N1C(=O)[C@H](Cc2ccnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c2)[C@H]1C(=O)NS(C)(=O)=O)c1ccccc1>ClCCl>C[C@@H](NC(=O)N1C(=O)[C@H](Cc2ccnc(N)c2)[C@H]1C(=O)NS(C)(=O)=O)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9fb793bea16643dfa66d04e0341185a6 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N[C@@H]2C(=O)NS(=O)(=O)c2ccc(F)cc2)ccn1.C[Si](C)(C)C=[N+]=[N-]>>CN(C(=O)[C@H]1NC(=O)[C@@H]1Cc1ccnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c1)S(=O)(=O)c1ccc(F)cc1 | C(C)(C)(C)OC(=O)N(C1=NC=CC(=C1)C[C@@H]1[C@H](NC1=O)C(=O)NS(=O)(=O)C1=CC=C(C=C1)F)C(=O)OC(C)(C)C.C1CCOC1.[Si](C)(C)(C)C=[N+]=[N-].C(C)(=O)OCC>>C(C)(C)(C)OC(=O)N(C1=NC=CC(=C1)C[C@@H]1[C@H](NC1=O)C(=O)N(C)S(=O)(=O)C1=CC=C(C=C1)F)C(=O)OC(C)(C)C | [NH:2]([C:3](=[O:4])[C@H:5]1[NH:6][C:7](=[O:8])[C@@H:9]1[CH2:10][c:11]1[cH:12][cH:13][n:14][c:15]([N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[cH:31]1)[S:32](=[O:33])(=[O:34])[c:35]1[cH:36][cH:37][c:38]([F:39])[cH:40][cH:41]1.C[Si](C)(C)[CH:1]=[... | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N[C@@H]2C(=O)NS(=O)(=O)c2ccc(F)cc2)ccn1.C[Si](C)(C)C=[N+]=[N-] | CN(C(=O)[C@H]1NC(=O)[C@@H]1Cc1ccnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c1)S(=O)(=O)c1ccc(F)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | N-methylation | b8166a506ecec5cea10c17e34aab949eefc88ad8f0b841c419171826c06d5789 | 2c805c7125c1275e0af90790ea4333ecee18b60d5d73c8234f7b5d4d728a49cd | O=C(NS(=O)(=O)c1ccccc1)[C@H]1NC(=O)[C@@H]1Cc1ccncc1 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].[#7:2]-[C:3]-[C:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10]>>[#7:2]-[C:3]-[C:4](=[O;D1;H0:5])-[N;H0;D3;+0:6](-[CH3;D1;+0:1])-[#16:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10] | 65 | [{"value": 65.0, "product": "C(C)(C)(C)OC(=O)N(C1=NC=CC(=C1)C[C@@H]1[C@H](NC1=O)C(=O)N(C)S(=O)(=O)C1=CC=C(C=C1)F)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of 98 (18 mg, 1.0 eq.) in MeOH: THF (1 mL: 300 uL) was added 2.0M TMSCHN2 in hexanes (266 uL, 17 eq.). After 15 minutes, TLC showed complete conversion of starting material. The reaction was poured into ethyl acetate and then washed with 0.2N HCl, 1N NaHCO3 and brine. The organic layer was then dried over... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Diazo.Secondary amide.Silyl protective group | Tertiary amide | null | null | C1CNC1.c1ccncc1.c1ccccc1 | Other | CO | null | 0.25 | CC(C)(C)OC(=O)N(C(=O)OC(C)(C)C)c1cc(C[C@H]2C(=O)N[C@@H]2C(=O)NS(=O)(=O)c2ccc(F)cc2)ccn1.C[Si](C)(C)C=[N+]=[N-]>CO>CN(C(=O)[C@H]1NC(=O)[C@@H]1Cc1ccnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c1)S(=O)(=O)c1ccc(F)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-53c7e8e6509e49dda10bd0d38ed95169 | CN(C(=O)[C@H]1NC(=O)[C@@H]1Cc1ccnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c1)S(=O)(=O)c1ccc(F)cc1.C[C@@H](N=C=O)c1ccccc1>>C[C@@H](NC(=O)N1C(=O)[C@H](Cc2ccnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c2)[C@H]1C(=O)N(C)S(=O)(=O)c1ccc(F)cc1)c1ccccc1 | C(C)(C)(C)OC(=O)N(C1=NC=CC(=C1)C[C@@H]1[C@H](NC1=O)C(=O)N(C)S(=O)(=O)C1=CC=C(C=C1)F)C(=O)OC(C)(C)C.C[C@H](C1=CC=CC=C1)N=C=O>>C(C)(C)(C)OC(=O)N(C1=NC=CC(=C1)C[C@@H]1[C@H](N(C1=O)C(=O)N[C@H](C)C1=CC=CC=C1)C(=O)N(C)S(=O)(=O)C1=CC=C(C=C1)F)C(=O)OC(C)(C)C | [NH:6]1[C:7](=[O:8])[C@H:9]([CH2:10][c:11]2[cH:12][cH:13][n:14][c:15]([N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[cH:31]2)[C@H:32]1[C:33](=[O:34])[N:35]([CH3:36])[S:37](=[O:38])(=[O:39])[c:40]1[cH:41][cH:42][c:43]([F:44])[cH:45][cH:46]1.[CH3:1]... | CN(C(=O)[C@H]1NC(=O)[C@@H]1Cc1ccnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c1)S(=O)(=O)c1ccc(F)cc1.C[C@@H](N=C=O)c1ccccc1 | C[C@@H](NC(=O)N1C(=O)[C@H](Cc2ccnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c2)[C@H]1C(=O)N(C)S(=O)(=O)c1ccc(F)cc1)c1ccccc1 | null | null | CN(C)C=O | Acylation | Urea synthesis via isocyanate and secondary amine | 105e9b64246d79f0e1854bc5e41627c9f514c23def37bcfaadf185ae4d2249f3 | d8031df9745ffb9494a0da2553ed47ba21f8143926e9537ff85149a4ef4cadb4 | O=C(NS(=O)(=O)c1ccccc1)[C@@H]1[C@@H](Cc2ccncc2)C(=O)N1C(=O)NCc1ccccc1 | [#16:1]-[#7:2](-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[C:6]1-[C:7]-[C:8](=[O;D1;H0:9])-[NH;D2;+0:10]-1.[C;D1;H3:11]-[C:12](-[c:13])-[N;H0;D2;+0:14]=[C;H0;D2;+0:15]=[O;D1;H0:16]>>[#16:1]-[#7:2](-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[C:6]1-[C:7]-[C:8](=[O;D1;H0:9])-[N;H0;D3;+0:10]-1-[C;H0;D3;+0:15](=[O;D1;H0:16])-[NH;D2;+0:14]-[C... | null | [] | null | null | 20 | HOUR | To a solution of 99 in DMF (0.75 mL) was added (R)-α-methylbenzylisocyanate (6 uL, 2.0 eq.) and TEA (8.5 uL, 3.0 eq.). The reaction was stirred under an atmosphere of argon for 20 hours. The reaction was then concentrated in vacuo and taken on to the next step without further purification.
Conditions: See reaction.note... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amide | Urea | C1CNC1 | C1C[NH]C1 | C1C[NH]C1.c1ccncc1.c1ccccc1.c1ccccc1 | null | CN(C)C=O | null | 20 | CN(C(=O)[C@H]1NC(=O)[C@@H]1Cc1ccnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c1)S(=O)(=O)c1ccc(F)cc1.C[C@@H](N=C=O)c1ccccc1>CN(C)C=O>C[C@@H](NC(=O)N1C(=O)[C@H](Cc2ccnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c2)[C@H]1C(=O)N(C)S(=O)(=O)c1ccc(F)cc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4eae807609d84181b764c388f79a50f0 | CCOC(=O)C=O.COc1ccc(N)cc1.O=C(Cl)COCc1ccccc1>>CCOC(=O)[C@@H]1[C@H](OCc2ccccc2)C(=O)N1c1ccc(OC)cc1 | COC1=CC=C(C=C1)N.C(C=O)(=O)OCC.S(=O)(=O)([O-])[O-].[Mg+2].C(C)N(CC)CC.C(C1=CC=CC=C1)OCC(=O)Cl>>C(C1=CC=CC=C1)O[C@H]1[C@H](N(C1=O)C1=CC=C(C=C1)OC)C(=O)OCC | O=[CH:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:18][c:19]1[cH:20][cH:21][c:22]([O:23][CH3:24])[cH:25][cH:26]1.Cl[C:16]([CH2:7][O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)=[O:17]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[C@H:7]([O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[C:16](=[O:17])[N:18]1[c:1... | CCOC(=O)C=O.COc1ccc(N)cc1.O=C(Cl)COCc1ccccc1 | CCOC(=O)[C@@H]1[C@H](OCc2ccccc2)C(=O)N1c1ccc(OC)cc1 | null | null | ClCCl.C1(=CC=CC=C1)C | Acylation | OtherReaction | 612ff11e6fbccac9c16b85d9b4a331f7ae3415a8a8adc1dcfd6c38c5f3fe462b | cbf12c2c4a767c032be93c2e7f8bad244097b91355198d91d7f7c3b1a4ee6ae5 | O=C1[C@@H](OCc2ccccc2)CN1c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:3]-[#8:4]-[C:5].O=[CH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10].[NH2;D1;+0:11]-[c:12](:[c:13]):[c:14]>>[C:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[C@@H;D3;+0:6]1-[C@H;D3;+0:3](-[#8:4]-[C:5])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11]-1-[c:12](:[c:13]):[c:14] | 69 | [{"value": 69.0, "product": "C(C1=CC=CC=C1)O[C@H]1[C@H](N(C1=O)C1=CC=C(C=C1)OC)C(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 18 | HOUR | To a solution of p-anisidine (107, 5.4 mmol) in 10 ml anhydrous dichloromethane and 2 ml toluene were added ethyl glyoxylate (8.0 mmol, 50% solution in toluene) and anhydrous magnesium sulfate (3.0 g). The reaction mixture was heated at 70° C. for 3 h. Afterwards, the mixture was filtered and cooled to 0° C. with an ic... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Ester.Ether.Primary amine | Ester.Ether.Tertiary amide | null | C1C[NH]C1 | C1C[NH]C1.c1ccccc1.c1ccccc1 | HCl | ClCCl.C1(=CC=CC=C1)C | 70 | 18 | CCOC(=O)C=O.COc1ccc(N)cc1.O=C(Cl)COCc1ccccc1>ClCCl.C1(=CC=CC=C1)C>CCOC(=O)[C@@H]1[C@H](OCc2ccccc2)C(=O)N1c1ccc(OC)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1a533b3d88814afb96514de5a313d730 | CC(C)[Si](S)(C(C)C)C(C)C.CCOC(=O)[C@@H]1[C@H](OS(=O)(=O)C(F)(F)F)C(=O)N1c1ccc(OC)cc1>>CCOC(=O)[C@@H]1[C@@H](S)C(=O)N1c1ccc(OC)cc1 | COC1=CC=C(C=C1)N1[C@@H]([C@@H](C1=O)OS(=O)(=O)C(F)(F)F)C(=O)OCC.C(C)(C)[Si](S)(C(C)C)C(C)C.[H-].[Na+]>>S[C@@H]1[C@H](N(C1=O)C1=CC=C(C=C1)OC)C(=O)OCC | CC(C)[Si](C(C)C)(C(C)C)[SH:8].O=S(=O)(O[C@H:7]1[C@@H:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[N:11]([c:12]2[cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18][cH:19]2)[C:9]1=[O:10])C(F)(F)F>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C@@H:6]1[C@@H:7]([SH:8])[C:9](=[O:10])[N:11]1[c:12]1[cH:13][cH:14][c:15]([O:16][CH3:17])[cH:18][cH:19]1 | CC(C)[Si](S)(C(C)C)C(C)C.CCOC(=O)[C@@H]1[C@H](OS(=O)(=O)C(F)(F)F)C(=O)N1c1ccc(OC)cc1 | CCOC(=O)[C@@H]1[C@@H](S)C(=O)N1c1ccc(OC)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | dba063a84f18745e4d72ac111177acf859c4b6fdd6211da6445ea86f50f62d6f | d183326bb9907be504acf631c53bc103ca43b88e4e09d4fc46ca672f0a6dd8a9 | O=C1CCN1c1ccccc1 | C-C(-C)-[Si](-[SH;D1;+0:1])(-C(-C)-C)-C(-C)-C.F-C(-F)(-F)-S(=O)(=O)-O-[C@H;D3;+0:2]1-[C:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7])-[#7:8](-[c:9])-[C:10]-1=[O;D1;H0:11]>>[C:7]-[#8:6]-[C:4](=[O;D1;H0:5])-[C:3]1-[#7:8](-[c:9])-[C:10](=[O;D1;H0:11])-[C@@H;D3;+0:2]-1-[SH;D1;+0:1] | null | [] | null | null | 15 | MINUTE | To a solution of triisopropylsilane thiol (0.91 mmol) in anhydrous THF (2 ml) was added sodium hydride (0.68 mmol, 60% in mineral oil) and the reaction mixture was stirred at room temperature for 15 min. Afterwards, compound 109 (0.45 mmol, dissolved in 2 ml THF) was added to the reaction and the mixture was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Silyl protective group | Aliphatic thiol | C1C[NH]C1 | C1C[NH]C1 | C1C[NH]C1.c1ccccc1 | TfOH.HO- | C1CCOC1 | null | 0.25 | CC(C)[Si](S)(C(C)C)C(C)C.CCOC(=O)[C@@H]1[C@H](OS(=O)(=O)C(F)(F)F)C(=O)N1c1ccc(OC)cc1>C1CCOC1>CCOC(=O)[C@@H]1[C@@H](S)C(=O)N1c1ccc(OC)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e223992e05b5407da52f7f612971053b | CC(C)(C)[Si](C)(C)N1C(=O)C[C@H]1C(=O)O.CC(C)c1cc(C(C)C)c(S(=O)(=O)N=[N+]=[N-])c(C(C)C)c1>>CC(C)(C)[Si](C)(C)N1C(=O)[C@H](N=[N+]=[N-])[C@H]1C(=O)O | [Li+].CC(C)[N-]C(C)C.[Si](C)(C)(C(C)(C)C)N1[C@@H](CC1=O)C(=O)O.CC(C)C1=CC(=C(C(=C1)C(C)C)S(=O)(=O)N=[N+]=[N-])C(C)C.N1CCC1>>N(=[N+]=[N-])[C@@H]1[C@H](N(C1=O)[Si](C)(C)C(C)(C)C)C(=O)O | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[N:8]1[C:9](=[O:10])[CH2:11][C@H:15]1[C:16](=[O:17])[OH:18].CC(C)c1cc(C(C)C)c(S(=O)(=O)[N:12]=[N+:13]=[N-:14])c(C(C)C)c1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[N:8]1[C:9](=[O:10])[C@H:11]([N:12]=[N+:13]=[N-:14])[C@H:15]1[C:16](=[O:17])[OH:18] | CC(C)(C)[Si](C)(C)N1C(=O)C[C@H]1C(=O)O.CC(C)c1cc(C(C)C)c(S(=O)(=O)N=[N+]=[N-])c(C(C)C)c1 | CC(C)(C)[Si](C)(C)N1C(=O)[C@H](N=[N+]=[N-])[C@H]1C(=O)O | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 3c31277475f2f47ae66d8c63f37b5f8030dc499e040230296dafebaeac1cc874 | 416557d8db25ba7ecc0f0d06f72e3202f6d89c7ade39dc289b802f47f65faae3 | O=C1CCN1 | C-C(-C)-c1:c:c(-C(-C)-C):c(-S(=O)(=O)-[N;H0;D2;+0:1]=[#7;+:2]=[N;-;D1;H0:3]):c(-C(-C)-C):c:1.[C:4]-[#14:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#7:8]1-[C:9](-[C:10](=[O;D1;H0:11])-[O;D1;H1:12])-[CH2;D2;+0:13]-[C:14]-1=[O;D1;H0:15]>>[C:4]-[#14:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[#7:8]1-[C:9](-[C:10](=[O;D1;H0:11])-[O;D1;H1:12])-[C@... | null | [] | -10 | CELSIUS | 30 | MINUTE | To LDA (1.8M, 4.99 mL) and THF (10 mL) at −78° C. was added dropwise (S)-1-t-butyldimethylsilyl-4-oxo-2-azetidinecarboxylic acid (4, 1.0 g) in THF (15 mL). The resulting solution was warmed to −30° C. or −10° C. for 30 min. If a slurry formed, additional THF was added to solublize the azetidine. After 30 min., the solu... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Azide | C1C[NH]C1.c1ccccc1 | C1C[NH]C1 | C1C[NH]C1 | HO- | C1CCOC1 | -10 | 0.5 | CC(C)(C)[Si](C)(C)N1C(=O)C[C@H]1C(=O)O.CC(C)c1cc(C(C)C)c(S(=O)(=O)N=[N+]=[N-])c(C(C)C)c1>C1CCOC1>CC(C)(C)[Si](C)(C)N1C(=O)[C@H](N=[N+]=[N-])[C@H]1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-635b4696e07342a98a906857c2e01f9a | CC(C)(C)[Si](C)(C)N1C(=O)[C@H](N=[N+]=[N-])[C@H]1C(=O)O.CO>>COC(=O)[C@@H]1[C@@H](N=[N+]=[N-])C(=O)N1[Si](C)(C)C(C)(C)C | C1CCC(CC1)N=C=NC2CCCCC2.N(=[N+]=[N-])[C@@H]1[C@H](N(C1=O)[Si](C)(C)C(C)(C)C)C(=O)O.CO>>N(=[N+]=[N-])[C@@H]1[C@H](N(C1=O)[Si](C)(C)C(C)(C)C)C(=O)OC | [OH:2][C:3](=[O:4])[C@@H:5]1[C@@H:6]([N:7]=[N+:8]=[N-:9])[C:10](=[O:11])[N:12]1[Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19].O[CH3:1]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[C@@H:6]([N:7]=[N+:8]=[N-:9])[C:10](=[O:11])[N:12]1[Si:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[CH3:19] | CC(C)(C)[Si](C)(C)N1C(=O)[C@H](N=[N+]=[N-])[C@H]1C(=O)O.CO | COC(=O)[C@@H]1[C@@H](N=[N+]=[N-])C(=O)N1[Si](C)(C)C(C)(C)C | null | CN(C)C=1C=CN=CC1 | C(Cl)Cl | Heteroatom Alkylation and Arylation | Esterification of Carboxylic Acids | 961bfcd5802efbb4a2d5a1e38cbfb6654b5b78f769c3570df49b858a6f105ab6 | 0a622556a49b258b9020bd3a5bdd1fa9237e7093cf9b09de3a6b575ffe935dcd | O=C1CCN1 | O-[CH3;D1;+0:1].[#7:2]-[C:3]-[C:4](=[O;D1;H0:5])-[OH;D1;+0:6]>>[#7:2]-[C:3]-[C:4](=[O;D1;H0:5])-[O;H0;D2;+0:6]-[CH3;D1;+0:1] | null | [] | null | null | 8 | HOUR | To a solution of crude 131 (1.58 g) in CH2Cl2 (25 mL) was added methanol (0.26 mL, 6.43 mmol). DCC (1.45 g, 7.02 mmol) and catalytic DMAP. The solution was stirred at room temperature overnight. The solution was then filtered through Celite and concentrated in vacuo. The crude product was purified by silica gel column ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | C1C[NH]C1 | HO- | CN(C)C=1C=CN=CC1.C(Cl)Cl | null | 8 | CC(C)(C)[Si](C)(C)N1C(=O)[C@H](N=[N+]=[N-])[C@H]1C(=O)O.CO>CN(C)C=1C=CN=CC1.C(Cl)Cl>COC(=O)[C@@H]1[C@@H](N=[N+]=[N-])C(=O)N1[Si](C)(C)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d28195f9c9524fe4962bc858c6a23a46 | COC(=O)[C@@H]1[C@@H](N=[N+]=[N-])C(=O)N1[Si](C)(C)C(C)(C)C>>COC(=O)[C@@H]1[C@@H](N)C(=O)N1[Si](C)(C)C(C)(C)C | N(=[N+]=[N-])[C@@H]1[C@H](N(C1=O)[Si](C)(C)C(C)(C)C)C(=O)OC.CO>>N[C@@H]1[C@H](N(C1=O)[Si](C)(C)C(C)(C)C)C(=O)OC | [N-]=[N+]=[N:7][C@@H:6]1[C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[N:10]([Si:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[CH3:17])[C:8]1=[O:9]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[C@@H:6]([NH2:7])[C:8](=[O:9])[N:10]1[Si:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[CH3:17] | COC(=O)[C@@H]1[C@@H](N=[N+]=[N-])C(=O)N1[Si](C)(C)C(C)(C)C | COC(=O)[C@@H]1[C@@H](N)C(=O)N1[Si](C)(C)C(C)(C)C | null | C(=O)(C(F)(F)F)O.[Pd] | O1CCOCC1 | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=C1CCN1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[#7:5](-[#14:6](-[C:7])(-[C;D1;H3:8])-[C;D1;H3:9])-[C:10](=[O;D1;H0:11])-[C:12]-1-[N;H0;D2;+0:13]=[N+]=[N-]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[#7:5](-[#14:6](-[C:7])(-[C;D1;H3:8])-[C;D1;H3:9])-[C:10](=[O;D1;H0:11])-[C:12]-1-[NH2;D1;+0:13] | null | [] | null | null | 1 | HOUR | To a solution of 132 (5.85 mmol) in 3:1 methanol:dioxane (25 mL) was added a few drops of TFA and 10% Pd/C (10 wt %). The reaction was stirred under atmospheric hydrogen for one hour and then filtered through Celite. The solvent was removed and the residue triturated with diethyl ether to afford 133, which was used in ... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | C1C[NH]C1 | Other | C(=O)(C(F)(F)F)O.[Pd].O1CCOCC1 | null | 1 | COC(=O)[C@@H]1[C@@H](N=[N+]=[N-])C(=O)N1[Si](C)(C)C(C)(C)C>C(=O)(C(F)(F)F)O.[Pd].O1CCOCC1>COC(=O)[C@@H]1[C@@H](N)C(=O)N1[Si](C)(C)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0344690b80aa4470a04818be6a64300e | [N-]=[N+]=NCCC[C@H]1C(=O)N[C@@H]1C(=O)O>>NCCC[C@H]1C(=O)N[C@@H]1C(=O)O | N(=[N+]=[N-])CCC[C@@H]1[C@H](NC1=O)C(=O)O>>NCCC[C@@H]1[C@H](NC1=O)C(=O)O | [N-]=[N+]=[N:1][CH2:2][CH2:3][CH2:4][C@H:5]1[C:6](=[O:7])[NH:8][C@@H:9]1[C:10](=[O:11])[OH:12]>>[NH2:1][CH2:2][CH2:3][CH2:4][C@H:5]1[C:6](=[O:7])[NH:8][C@@H:9]1[C:10](=[O:11])[OH:12] | [N-]=[N+]=NCCC[C@H]1C(=O)N[C@@H]1C(=O)O | NCCC[C@H]1C(=O)N[C@@H]1C(=O)O | null | [Pd] | C(C)(=O)O.CN(C)C=O | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | O=C1CCN1 | [C:1]-[C:2]-[N;H0;D2;+0:3]=[N+]=[N-]>>[C:1]-[C:2]-[NH2;D1;+0:3] | null | [] | null | null | 16 | HOUR | To a solution of 146 (0.59 g, 1.0 eq.) in DMF (5 mL) and acetic acid (1 mL) was added 10% Pd/C (300 mg). The flask was evacuated and flushed with hydrogen. The reaction was then stirred at room temperature under an atmosphere of hydrogen for 16 hours. The reaction was then filtered through Celite and crude amine 147 wa... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | C1CNC1 | Other | [Pd].C(C)(=O)O.CN(C)C=O | null | 16 | [N-]=[N+]=NCCC[C@H]1C(=O)N[C@@H]1C(=O)O>[Pd].C(C)(=O)O.CN(C)C=O>NCCC[C@H]1C(=O)N[C@@H]1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da54d3c9ece84e808cacb59e3ff66d48 | O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N[C@@H]1C(=O)O)NC(=O)CCc1ccccc1.OCc1ccccc1>>O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccccc1)NC(=O)CCc1ccccc1 | C1(=CC=CC=C1)CCC(=O)/N=C(\NCCC[C@@H]1[C@H](NC1=O)C(=O)O)/NC(CCC1=CC=CC=C1)=O.C(C1=CC=CC=C1)O.CCN=C=NCCCN(C)C.Cl.C=1C=CC2=C(C1)N=NN2O.CCN(C(C)C)C(C)C>>C1(=CC=CC=C1)CCC(=O)/N=C(\NCCC[C@@H]1[C@H](NC1=O)C(=O)OCC1=CC=CC=C1)/NC(CCC1=CC=CC=C1)=O | O[C:22]([C@@H:21]1[C@@H:17]([CH2:16][CH2:15][CH2:14][NH:13]/[C:12](=[N:11]\[C:2](=[O:1])[CH2:3][CH2:4][c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[NH:32][C:33](=[O:34])[CH2:35][CH2:36][c:37]2[cH:38][cH:39][cH:40][cH:41][cH:42]2)[C:18](=[O:19])[NH:20]1)=[O:23].[OH:24][CH2:25][c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1>>[O:1]... | O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N[C@@H]1C(=O)O)NC(=O)CCc1ccccc1.OCc1ccccc1 | O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccccc1)NC(=O)CCc1ccccc1 | null | null | CN(C)C=O.C(C)(=O)OCC | Acylation | Esterification of Carboxylic Acids | d9bd78214ee7dbc907e499722ae01849a72d188753963443e5df9fe42c31c43b | 3652e761944e8ef7ee40675a156c8ae39909c72166786934d88652debf2ec1ac | O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccccc1)NC(=O)CCc1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[#7:4]-[C:5](=[O;D1;H0:6])-[C:7]-1.[OH;D1;+0:8]-[C:9]-[c:10]>>[O;D1;H0:6]=[C:5]1-[#7:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:8]-[C:9]-[c:10])-[C:7]-1 | null | [] | null | null | 16 | HOUR | To a solution of 148 (74 mg, 1.0 eq.) in DMF (1.5 mL) was added benzyl alcohol (19 uL, 1.2 eq.), EDC-HCl (35 mg, 1.2 eq.), HOBt (24 mg, 1.2 eq.) and DIEA (60 μL eq.). The reaction was stirred at room temperature for 16 hours and then diluted with ethyl acetate and washed with 1N HCl. The aqueous layer was then washed w... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Ester | null | null | c1ccccc1.C1CNC1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O.C(C)(=O)OCC | null | 16 | O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N[C@@H]1C(=O)O)NC(=O)CCc1ccccc1.OCc1ccccc1>CN(C)C=O.C(C)(=O)OCC>O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccccc1)NC(=O)CCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f7ba94c40f7f47568554f0e3ad840335 | O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccccc1)NC(=O)CCc1ccccc1.O=C=Nc1ccccc1>>O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N(C(=O)Nc2ccccc2)[C@@H]1C(=O)OCc1ccccc1)NC(=O)CCc1ccccc1 | C1(=CC=CC=C1)CCC(=O)/N=C(\NCCC[C@@H]1[C@H](NC1=O)C(=O)OCC1=CC=CC=C1)/NC(CCC1=CC=CC=C1)=O.C1(=CC=CC=C1)N=C=O.C(C)N(CC)CC>>C1(=CC=CC=C1)CCC(=O)/N=C(\NCCC[C@@H]1[C@H](N(C1=O)C(NC1=CC=CC=C1)=O)C(=O)OCC1=CC=CC=C1)/NC(CCC1=CC=CC=C1)=O | [O:1]=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)/[N:11]=[C:12](\[NH:13][CH2:14][CH2:15][CH2:16][C@H:17]1[C:18](=[O:19])[NH:20][C@@H:30]1[C:31](=[O:32])[O:33][CH2:34][c:35]1[cH:36][cH:37][cH:38][cH:39][cH:40]1)[NH:41][C:42](=[O:43])[CH2:44][CH2:45][c:46]1[cH:47][cH:48][cH:49][cH:50][cH:51]1.[C:21](=[O:2... | O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccccc1)NC(=O)CCc1ccccc1.O=C=Nc1ccccc1 | O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N(C(=O)Nc2ccccc2)[C@@H]1C(=O)OCc1ccccc1)NC(=O)CCc1ccccc1 | null | CN(C)C=1C=CN=CC1 | ClCCl.C(Cl)Cl | Acylation | Urea synthesis via isocyanate and secondary amine | 105e9b64246d79f0e1854bc5e41627c9f514c23def37bcfaadf185ae4d2249f3 | d8031df9745ffb9494a0da2553ed47ba21f8143926e9537ff85149a4ef4cadb4 | O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N(C(=O)Nc2ccccc2)[C@@H]1C(=O)OCc1ccccc1)NC(=O)CCc1ccccc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]1-[C:6]-[C:7](=[O;D1;H0:8])-[NH;D2;+0:9]-1.[O;D1;H0:10]=[C;H0;D2;+0:11]=[N;H0;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C:5]1-[C:6]-[C:7](=[O;D1;H0:8])-[N;H0;D3;+0:9]-1-[C;H0;D3;+0:11](=[O;D1;H0:10])-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15] | null | [] | null | null | 18 | HOUR | To a solution of 149 (50 mg, 1.0 eq.) in DCM (2 mL) was added phenylisocyanate (29 μL, 3.0 eq.), triethylamine (12 μL, 1 eq.) and DMAP (1 mg). The reaction was stirred for 18 hours at room temperature and then diluted with dichloromethane and washed with 1N HCl and water. The organic layer was then concentrated in vacu... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Secondary amide | Urea | C1CNC1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1.c1ccccc1.c1ccccc1.c1ccccc1 | null | CN(C)C=1C=CN=CC1.ClCCl.C(Cl)Cl | null | 18 | O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N[C@@H]1C(=O)OCc1ccccc1)NC(=O)CCc1ccccc1.O=C=Nc1ccccc1>CN(C)C=1C=CN=CC1.ClCCl.C(Cl)Cl>O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N(C(=O)Nc2ccccc2)[C@@H]1C(=O)OCc1ccccc1)NC(=O)CCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f39051919455464f8b3b64569b064009 | O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N(C(=O)Nc2ccccc2)[C@@H]1C(=O)OCc1ccccc1)NC(=O)CCc1ccccc1>>N=C(N)NCCC[C@H]1C(=O)N(C(=O)Nc2ccccc2)[C@@H]1C(=O)O | C1(=CC=CC=C1)CCC(=O)/N=C(\NCCC[C@@H]1[C@H](N(C1=O)C(NC1=CC=CC=C1)=O)C(=O)OCC1=CC=CC=C1)/NC(CCC1=CC=CC=C1)=O>>N(C(=N)N)CCC[C@@H]1[C@H](N(C1=O)C(NC1=CC=CC=C1)=O)C(=O)O | O=C(CCc1ccccc1)/[N:1]=[C:2](/[NH:3]C(=O)CCc1ccccc1)[NH:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C:9](=[O:10])[N:11]([C:12](=[O:13])[NH:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[C@@H:21]1[C:22](=[O:23])[O:24]Cc1ccccc1>>[NH:1]=[C:2]([NH2:3])[NH:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C:9](=[O:10])[N:11]([C:12](=[O:13])[NH:14][c:15]... | O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N(C(=O)Nc2ccccc2)[C@@H]1C(=O)OCc1ccccc1)NC(=O)CCc1ccccc1 | N=C(N)NCCC[C@H]1C(=O)N(C(=O)Nc2ccccc2)[C@@H]1C(=O)O | null | [Pd] | Cl.C1CCOC1 | Reduction | OtherReaction | e12ce4043eeea45fbb27ad40db5402dfdae4ea0fc0b2f41f852f185adb8bcdfb | 01841db25d7c9417dbf2fcab7fb91f3616b53926525501ef73813a86303e5c4c | O=C1CCN1C(=O)Nc1ccccc1 | O=C(-C-C-c1:c:c:c:c:c:1)/[N;H0;D2;+0:1]=[C:2](\[#7:3])-[NH;D2;+0:4]-C(=O)-C-C-c1:c:c:c:c:c:1.[#7:5]-[C:6]-[C:7](=[O;D1;H0:8])-[O;H0;D2;+0:9]-C-c1:c:c:c:c:c:1>>[#7:3]-[C:2](-[NH2;D1;+0:4])=[NH;D1;+0:1].[#7:5]-[C:6]-[C:7](=[O;D1;H0:8])-[OH;D1;+0:9] | 10.3 | [{"value": 10.3, "product": "N(C(=N)N)CCC[C@@H]1[C@H](N(C1=O)C(NC1=CC=CC=C1)=O)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a solution of 150 (10 mg, 1.0 eq.) in THF (3 mL) and 1N HCl (0.5 mL) was added 10% Pd/C (20 mg). The reaction flask was then evacuated and flushed with hydrogen and stirred under an atmosphere of hydrogen for 18 hours. The reaction was then filtered through Celite and concentrated in vacuo. The crude material was pu... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide | Carboxylic acid.Primary amine | c1ccccc1.c1ccccc1.c1ccccc1 | null | C1C[NH]C1.c1ccccc1 | HO- | [Pd].Cl.C1CCOC1 | null | 18 | O=C(CCc1ccccc1)/N=C(\NCCC[C@H]1C(=O)N(C(=O)Nc2ccccc2)[C@@H]1C(=O)OCc1ccccc1)NC(=O)CCc1ccccc1>[Pd].Cl.C1CCOC1>N=C(N)NCCC[C@H]1C(=O)N(C(=O)Nc2ccccc2)[C@@H]1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d647f58fb874166afaaea5daf759659 | N#Cc1cnccn1.[Cl-].[NH4+]>>Cl.N=C(N)c1cnccn1 | CO.N1=C(C=NC=C1)C#N.C[O-].[Na+].C[O-].[Na+].[Cl-].[NH4+]>>Cl.N1=C(C=NC=C1)C(=N)N | [N:2]#[C:3][c:5]1[cH:6][n:7][cH:8][cH:9][n:10]1.[Cl-:1].[NH4+:4]>>[ClH:1].[NH:2]=[C:3]([NH2:4])[c:5]1[cH:6][n:7][cH:8][cH:9][n:10]1 | N#Cc1cnccn1.[Cl-].[NH4+] | Cl.N=C(N)c1cnccn1 | null | null | C(C)(C)(C)OC | Functional Group Interconversion | OtherReaction | 3b047a13c16a607c445b1c419e256808e8c9a0097d8fb9efd4e7970deb782b70 | 2882e57127fc469aa16ca9a2fd53388b6d97c74c76c010e6eb01be5726f46aa5 | c1cnccn1 | [Cl-;H0;D0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:1.[NH4+;D0:10]>>[ClH;D0;+0:1].[NH2;D1;+0:10]-[C;H0;D3;+0:3](=[NH;D1;+0:2])-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:1 | null | [] | null | null | 22.5 | MINUTE | According to Scheme 1, step a, pyrazine-2-carbonitrile 1 is reacted in an alcohol solvent, preferably methyl alcohol in the presence of base A selected from an alkali metal hydroxide or alkali metal alkoxide, preferably sodium methoxide and more preferably sodium methoxide in a ratio of about 1:1 (mole/mole) in the tem... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1cnccn1 | null | C(C)(C)(C)OC | null | 0.375 | N#Cc1cnccn1.[Cl-].[NH4+]>C(C)(C)(C)OC>Cl.N=C(N)c1cnccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-752c3064797e4b33b13060c6aef298ec | O=P(Cl)(Cl)Cl.O=P(Cl)(Cl)Cl.Oc1nc(-c2cnccn2)nc(O)c1-c1c(F)cc(F)cc1F>>Fc1cc(F)c(-c2c(Cl)nc(-c3cnccn3)nc2Cl)c(F)c1 | ClCCl.P(=O)(Cl)(Cl)Cl.P(=O)(Cl)(Cl)Cl.C(C)(C)N(C(C)C)CC.N1=C(C=NC=C1)C1=NC(=C(C(=N1)O)C1=C(C=C(C=C1F)F)F)O>>ClC1=NC(=NC(=C1C1=C(C=C(C=C1F)F)F)Cl)C1=NC=CN=C1 | O=P(Cl)(Cl)[Cl:9].O=P(Cl)(Cl)[Cl:20].O[c:8]1[c:7](-[c:6]2[c:4]([F:5])[cH:3][c:2]([F:1])[cH:23][c:21]2[F:22])[c:19](O)[n:18][c:11](-[c:12]2[cH:13][n:14][cH:15][cH:16][n:17]2)[n:10]1>>[F:1][c:2]1[cH:3][c:4]([F:5])[c:6](-[c:7]2[c:8]([Cl:9])[n:10][c:11](-[c:12]3[cH:13][n:14][cH:15][cH:16][n:17]3)[n:18][c:19]2[Cl:20])[c:21]... | O=P(Cl)(Cl)Cl.O=P(Cl)(Cl)Cl.Oc1nc(-c2cnccn2)nc(O)c1-c1c(F)cc(F)cc1F | Fc1cc(F)c(-c2c(Cl)nc(-c3cnccn3)nc2Cl)c(F)c1 | null | null | C1(=CC=CC=C1)C.C(C)(=O)OCC | Functional Group Addition | OtherReaction | 7b64c81684e6de37d41d67ce30e3f1ac5e0648815fef2495837e76562b6b8616 | d74bc1b012061488363cc8b67469d047228fe70d9f227566212bf2539e8291df | c1ccc(-c2cnc(-c3cnccn3)nc2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:2].O-[c;H0;D3;+0:3]1:[#7;a:4]:[c:5](-[c:6](:[#7;a:7]):[c:8]:[#7;a:9]):[#7;a:10]:[c;H0;D3;+0:11](-O):[c:12]:1-[c:13]>>[#7;a:9]:[c:8]:[c:6](-[c:5]1:[#7;a:10]:[c;H0;D3;+0:11](-[Cl;H0;D1;+0:1]):[c:12](-[c:13]):[c;H0;D3;+0:3](-[Cl;H0;D1;+0:2]):[#7;a:4]:1):[#7;a:7] | null | [] | 10 | CELSIUS | null | null | According to scheme 1, step c, to a mixture of 2-pyrazin-2-yl-5-(2,4,6-trifluoro-phenyl)-pyrimidine-4,6-diol 4 in an aprotic solvent preferably toluene (g/ml) preferably 5-15 parts, more preferably in 5-10 parts, most preferable in 7 parts, is slowly added at about 10-15° C., phosphorus oxychloride. Following complete ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Aromatic alcohol | Aromatic halide.Aromatic halide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1cnccn1 | HCl | C1(=CC=CC=C1)C.C(C)(=O)OCC | 10 | null | O=P(Cl)(Cl)Cl.O=P(Cl)(Cl)Cl.Oc1nc(-c2cnccn2)nc(O)c1-c1c(F)cc(F)cc1F>C1(=CC=CC=C1)C.C(C)(=O)OCC>Fc1cc(F)c(-c2c(Cl)nc(-c3cnccn3)nc2Cl)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b2392e773864b249106f5bc0b76f0ef | C[C@H](N)C(F)(F)F.Fc1cc(F)c(-c2c(Cl)nc(-c3cnccn3)nc2Cl)c(F)c1>>C[C@H](Nc1nc(-c2cnccn2)nc(Cl)c1-c1c(F)cc(F)cc1F)C(F)(F)F | FC([C@H](C)N)(F)F.O.O.ClC1=NC(=NC(=C1C1=C(C=C(C=C1F)F)F)Cl)C1=NC=CN=C1.ClC1=NC(=NC(=C1C1=C(C=C(C=C1F)F)F)Cl)C1=NC=CN=C1.ClC1=NC(=NC(=C1C1=C(C=C(C=C1F)F)F)Cl)C1=NC=CN=C1.ClC1=NC(=NC(=C1C1=C(C=C(C=C1F)F)F)Cl)C1=NC=CN=C1.FC([C@H](C)N)(F)F.ClC1=NC(=NC(=C1C1=C(C=C(C=C1F)F)F)Cl)C1=NC=CN=C1.FC([C@H](C)N)(F)F>>ClC1=C(C(=NC(=N1... | [CH3:1][C@H:2]([NH2:3])[C:26]([F:27])([F:28])[F:29].Cl[c:4]1[n:5][c:6](-[c:7]2[cH:8][n:9][cH:10][cH:11][n:12]2)[n:13][c:14]([Cl:15])[c:16]1-[c:17]1[c:18]([F:19])[cH:20][c:21]([F:22])[cH:23][c:24]1[F:25]>>[CH3:1][C@H:2]([NH:3][c:4]1[n:5][c:6](-[c:7]2[cH:8][n:9][cH:10][cH:11][n:12]2)[n:13][c:14]([Cl:15])[c:16]1-[c:17]1[c... | C[C@H](N)C(F)(F)F.Fc1cc(F)c(-c2c(Cl)nc(-c3cnccn3)nc2Cl)c(F)c1 | C[C@H](Nc1nc(-c2cnccn2)nc(Cl)c1-c1c(F)cc(F)cc1F)C(F)(F)F | null | null | CN1C(CCC1)=O.C(C)(C)O.CN1CCCC1=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2cnc(-c3cnccn3)nc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[c:8].[C;D1;H3:9]-[C:10](-[NH2;D1;+0:11])-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[F;D1;H0:15]>>[C;D1;H3:9]-[C:10](-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[c:8])-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[F;D1;H0... | 92 | [{"value": 92.0, "product": "ClC1=C(C(=NC(=N1)C1=NC=CN=C1)N[C@H](C(F)(F)F)C)C1=C(C=C(C=C1F)F)F", "details": "PERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 24 | HOUR | In scheme 1, step d, a solution of 4,6-dichloro-2-pyrazin-2-yl-5-(2,4,6-trifluoro-phenyl)-pyrimidine 5 in an aprotic solvent, preferably 1-methyl-2-pyrrolidinone (NMP) in a ratio of 1-10 mL NMP/g of 4,6-dichloro-2-pyrazin-2-yl-5-(2,4,6-trifluoro-phenyl)-pyrimidine 5, preferably 1-5 mL NMP/g of 4,6-dichloro-2-pyrazin-2-... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1cnccn1.c1ccccc1 | HCl | CN1C(CCC1)=O.C(C)(C)O.CN1CCCC1=O | 110 | 24 | C[C@H](N)C(F)(F)F.Fc1cc(F)c(-c2c(Cl)nc(-c3cnccn3)nc2Cl)c(F)c1>CN1C(CCC1)=O.C(C)(C)O.CN1CCCC1=O>C[C@H](Nc1nc(-c2cnccn2)nc(Cl)c1-c1c(F)cc(F)cc1F)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a8b98767deda4894a482860eed95169e | N#Cc1cnccn1.[Cl-].[NH4+]>>Cl.N=C(N)c1cnccn1 | C(C)(C)(C)OC.[Cl-].[NH4+].C[O-].[Na+].C(#N)C1=NC=CN=C1>>Cl.N1=C(C=NC=C1)C(=N)N | [N:2]#[C:3][c:5]1[cH:6][n:7][cH:8][cH:9][n:10]1.[Cl-:1].[NH4+:4]>>[ClH:1].[NH:2]=[C:3]([NH2:4])[c:5]1[cH:6][n:7][cH:8][cH:9][n:10]1 | N#Cc1cnccn1.[Cl-].[NH4+] | Cl.N=C(N)c1cnccn1 | null | null | CO | Functional Group Interconversion | OtherReaction | 3b047a13c16a607c445b1c419e256808e8c9a0097d8fb9efd4e7970deb782b70 | 2882e57127fc469aa16ca9a2fd53388b6d97c74c76c010e6eb01be5726f46aa5 | c1cnccn1 | [Cl-;H0;D0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:1.[NH4+;D0:10]>>[ClH;D0;+0:1].[NH2;D1;+0:10]-[C;H0;D3;+0:3](=[NH;D1;+0:2])-[c:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:1 | 95 | [{"value": 95.0, "product": "Cl.N1=C(C=NC=C1)C(=N)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.9, "product": "Cl.N1=C(C=NC=C1)C(=N)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 30 | CELSIUS | 6 | HOUR | To a solution of sodium methoxide (NaOCH3) (51.4 g, 0.952 mol) in methanol (3800 ml) there is added cyanopyrazine (1.00 KG, 9.53 mol) slowly at room temperature. The mixture is heated to 30° C. and stirred for 6 h. The mixture is cooled to 25° C. followed by the addition of ammonium chloride (NH4Cl) (572 g, 10.5 mol). ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1cnccn1 | null | CO | 30 | 6 | N#Cc1cnccn1.[Cl-].[NH4+]>CO>Cl.N=C(N)c1cnccn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-252942e734964243b4841b66e777af90 | CCOC(=O)C(C(=O)OCC)c1c(F)cc(F)cc1F.N=C(N)c1cnccn1>>Oc1nc(-c2cnccn2)nc(O)c1-c1c(F)cc(F)cc1F | Cl.C(C)OC(C(C(=O)OCC)C1=C(C=C(C=C1F)F)F)=O.Cl.N1=C(C=NC=C1)C(=N)N.C([O-])([O-])=O.[K+].[K+]>>N1=C(C=NC=C1)C1=NC(=C(C(=N1)O)C1=C(C=C(C=C1F)F)F)O | CCO[C:2](=[O:1])[CH:14]([C:12](OCC)=[O:13])[c:15]1[c:16]([F:17])[cH:18][c:19]([F:20])[cH:21][c:22]1[F:23].[NH:3]=[C:4]([c:5]1[cH:6][n:7][cH:8][cH:9][n:10]1)[NH2:11]>>[OH:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][n:7][cH:8][cH:9][n:10]2)[n:11][c:12]([OH:13])[c:14]1-[c:15]1[c:16]([F:17])[cH:18][c:19]([F:20])[cH:21][c:22]1[F:23] | CCOC(=O)C(C(=O)OCC)c1c(F)cc(F)cc1F.N=C(N)c1cnccn1 | Oc1nc(-c2cnccn2)nc(O)c1-c1c(F)cc(F)cc1F | null | null | O.C(C)(=O)O.COCCOCCOC | Aromatic Heterocycle Formation | OtherReaction | d507ea5e988c6bcfe927f1b3a86f934f8a1c706f38171153cdf4dbd7aeb28e83 | 6504f33921726f64e36c5f3f322459b73652319c83071522ec21b8b88a33a5a7 | c1ccc(-c2cnc(-c3cnccn3)nc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-O-C-C)-[c;H0;D3;+0:6](:[c:7](-[F;D1;H0:8]):[c:9]):[c:10](-[F;D1;H0:11]):[c:12].[NH2;D1;+0:13]-[C;H0;D3;+0:14](=[NH;D1;+0:15])-[c;H0;D3;+0:16]1:[#7;a:17]:[c:18]:[c:19]:[#7;a:20]:[c:21]:1>>[F;D1;H0:8]-[c:7](:[c:9]):[c;H0;D3;+0:6](-[c;H0;D... | 69 | [{"value": 69.0, "product": "N1=C(C=NC=C1)C1=NC(=C(C(=N1)O)C1=C(C=C(C=C1F)F)F)O", "details": "PERCENTYIELD", "is_desired": false}] | 120 | CELSIUS | 4 | HOUR | A mixture of 2-(2,4,6-trifluoro-phenyl)-malonic acid diethyl ester (200 g, 0.67 mol), pyrazine-2-carboxamidine hydrochloride (132 g, 0.828 mol) and potassium carbonate (114 g, 0.828 mol) in 2-methyoxyethyl ether (diglyme, 600 mL) is heated to 120° C. and stirred for 4 h, then heated to 140° C. and stirred for an additi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Aromatic alcohol.Aromatic alcohol | null | c1cncnc1 | c1cncnc1.c1cnccn1.c1ccccc1 | HO- | O.C(C)(=O)O.COCCOCCOC | 120 | 4 | CCOC(=O)C(C(=O)OCC)c1c(F)cc(F)cc1F.N=C(N)c1cnccn1>O.C(C)(=O)O.COCCOCCOC>Oc1nc(-c2cnccn2)nc(O)c1-c1c(F)cc(F)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5d2ff3be2806481b854e791bfbad5d2a | CCOC(=O)C(C(=O)OCC)c1c(F)cc(F)cc1F.N=C(N)c1cnccn1>>Oc1nc(-c2cnccn2)nc(O)c1-c1c(F)cc(F)cc1F | Cl.N12CCCCCC2=NCCC1.C(C)OC(C(C(=O)OCC)C1=C(C=C(C=C1F)F)F)=O.Cl.N1=C(C=NC=C1)C(=N)N>>N1=C(C=NC=C1)C1=NC(=C(C(=N1)O)C1=C(C=C(C=C1F)F)F)O | CCO[C:2](=[O:1])[CH:14]([C:12](OCC)=[O:13])[c:15]1[c:16]([F:17])[cH:18][c:19]([F:20])[cH:21][c:22]1[F:23].[NH:3]=[C:4]([c:5]1[cH:6][n:7][cH:8][cH:9][n:10]1)[NH2:11]>>[OH:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][n:7][cH:8][cH:9][n:10]2)[n:11][c:12]([OH:13])[c:14]1-[c:15]1[c:16]([F:17])[cH:18][c:19]([F:20])[cH:21][c:22]1[F:23] | CCOC(=O)C(C(=O)OCC)c1c(F)cc(F)cc1F.N=C(N)c1cnccn1 | Oc1nc(-c2cnccn2)nc(O)c1-c1c(F)cc(F)cc1F | null | null | O.CN1C(CCC1)=O | Aromatic Heterocycle Formation | OtherReaction | d507ea5e988c6bcfe927f1b3a86f934f8a1c706f38171153cdf4dbd7aeb28e83 | 6504f33921726f64e36c5f3f322459b73652319c83071522ec21b8b88a33a5a7 | c1ccc(-c2cnc(-c3cnccn3)nc2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH;D3;+0:3](-[C;H0;D3;+0:4](=[O;H0;D1;+0:5])-O-C-C)-[c;H0;D3;+0:6](:[c:7](-[F;D1;H0:8]):[c:9]):[c:10](-[F;D1;H0:11]):[c:12].[NH2;D1;+0:13]-[C;H0;D3;+0:14](=[NH;D1;+0:15])-[c;H0;D3;+0:16]1:[#7;a:17]:[c:18]:[c:19]:[#7;a:20]:[c:21]:1>>[F;D1;H0:8]-[c:7](:[c:9]):[c;H0;D3;+0:6](-[c;H0;D... | 76 | [{"value": 76.0, "product": "N1=C(C=NC=C1)C1=NC(=C(C(=N1)O)C1=C(C=C(C=C1F)F)F)O", "details": "PERCENTYIELD", "is_desired": false}] | 95 | CELSIUS | 7 | HOUR | 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU; 14.4 g, 0.0944 mol) is added to a mixture of 2-(2,4,6-triflorophenyl)malonic acid diethyl ester (14.3 g, 0.0472 mol) and pyrazine-2-carboxamidine hydrochloride (9.00 g, 0.0566 mol) in 1-methyl-2-pyrrolidinone (NMP; 50 mL) solvent. The resulting mixture is heated to 95° C. while ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Primary amine | Aromatic alcohol.Aromatic alcohol | null | c1cncnc1 | c1cncnc1.c1cnccn1.c1ccccc1 | HO- | O.CN1C(CCC1)=O | 95 | 7 | CCOC(=O)C(C(=O)OCC)c1c(F)cc(F)cc1F.N=C(N)c1cnccn1>O.CN1C(CCC1)=O>Oc1nc(-c2cnccn2)nc(O)c1-c1c(F)cc(F)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f062e1ba405e423b9197db05522f3eb5 | C[C@H](N)C(F)(F)F.Fc1cc(F)c(-c2c(Cl)nc(-c3cnccn3)nc2Cl)c(F)c1>>C[C@H](Nc1nc(-c2cnccn2)nc(Cl)c1-c1c(F)cc(F)cc1F)C(F)(F)F | ClC1=NC(=NC(=C1C1=C(C=C(C=C1F)F)F)Cl)C1=NC=CN=C1.FC([C@H](C)N)(F)F>>ClC1=C(C(=NC(=N1)C1=NC=CN=C1)N[C@H](C(F)(F)F)C)C1=C(C=C(C=C1F)F)F | [CH3:1][C@H:2]([NH2:3])[C:26]([F:27])([F:28])[F:29].Cl[c:4]1[n:5][c:6](-[c:7]2[cH:8][n:9][cH:10][cH:11][n:12]2)[n:13][c:14]([Cl:15])[c:16]1-[c:17]1[c:18]([F:19])[cH:20][c:21]([F:22])[cH:23][c:24]1[F:25]>>[CH3:1][C@H:2]([NH:3][c:4]1[n:5][c:6](-[c:7]2[cH:8][n:9][cH:10][cH:11][n:12]2)[n:13][c:14]([Cl:15])[c:16]1-[c:17]1[c... | C[C@H](N)C(F)(F)F.Fc1cc(F)c(-c2c(Cl)nc(-c3cnccn3)nc2Cl)c(F)c1 | C[C@H](Nc1nc(-c2cnccn2)nc(Cl)c1-c1c(F)cc(F)cc1F)C(F)(F)F | null | null | O.CC(C)O.CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2cnc(-c3cnccn3)nc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[c:8].[C;D1;H3:9]-[C:10](-[NH2;D1;+0:11])-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[F;D1;H0:15]>>[C;D1;H3:9]-[C:10](-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[c:8])-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[F;D1;H0... | 84 | [{"value": 84.0, "product": "ClC1=C(C(=NC(=N1)C1=NC=CN=C1)N[C@H](C(F)(F)F)C)C1=C(C=C(C=C1F)F)F", "details": "PERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 24 | HOUR | To 4,6-dichloro-2-pyrazin-2-yl-5-(2,4,6-trifluoro-phenyl)-pyrimidine (40 g, 0.112 mol) in 1-methyl-2-pyrrolidinone (40 mL) there is added (S)-2,2,2-trifluoro-1-methyl-ethylamine (31.6 g, 0.28 mol). The mixture is sealed and heated to 110° C. and stirred for 24 h. The reaction mixture is cooled to room temperature and d... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1cnccn1.c1ccccc1 | HCl | O.CC(C)O.CN1C(CCC1)=O | 110 | 24 | C[C@H](N)C(F)(F)F.Fc1cc(F)c(-c2c(Cl)nc(-c3cnccn3)nc2Cl)c(F)c1>O.CC(C)O.CN1C(CCC1)=O>C[C@H](Nc1nc(-c2cnccn2)nc(Cl)c1-c1c(F)cc(F)cc1F)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c391bf99df534663a7c96a7ab4abfa3f | CCOC(=O)c1ccc(N)cc1.N#CN>>CCOC(=O)c1ccc(NC(=N)N)cc1 | C(C)OC(C1=CC=C(C=C1)N)=O.[N+](=O)(O)[O-].N#CN>>[N+](=O)(O)[O-].C(C)OC(C1=CC=C(C=C1)NC(=N)N)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:14][cH:15]1.[C:11](#[N:12])[NH2:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH:10][C:11](=[NH:12])[NH2:13])[cH:14][cH:15]1 | CCOC(=O)c1ccc(N)cc1.N#CN | CCOC(=O)c1ccc(NC(=N)N)cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | a0cbddf5d7d81fe92104447f1edef14329807abeadc66f8268b3c04bddc38ea2 | 9b168a0be416143e92b99e2902110a4569d3f9f31721e83b72aa42867628c64d | c1ccccc1 | [N;D1;H2:1]-[C;H0;D2;+0:2]#[N;H0;D1;+0:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[N;D1;H2:1]-[C;H0;D3;+0:2](=[NH;D1;+0:3])-[NH;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 24 | HOUR | 4-aminobenzoic acid ethyl ester (20 g, 0.121 mol), nitric acid (7.26 g, 0.121 mol), cyanamide (50%, 14 ml 0.182 mol) were mixed under reflux with ethanol (50 ml). After 24 hr, the mixture was cooled to RT, and then washed with ethanol to give the titled compound as crystalline solid.
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Cyanamide.Primary amine | Secondary amine | null | null | c1ccccc1 | null | C(C)O | null | 24 | CCOC(=O)c1ccc(N)cc1.N#CN>C(C)O>CCOC(=O)c1ccc(NC(=N)N)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a3ab26ef0c94b18b0dc85955333fe47 | CCOC(=O)c1ccc(C)c(NC(=N)N)c1.CN(C)/C=C/C(=O)c1cnccn1>>CCOC(=O)c1ccc(C)c(Nc2nccc(-c3cnccn3)n2)c1 | [N+](=O)(O)[O-].C(C)OC(C1=CC=C(C=C1)NC(=N)N)=O.CN(C)/C=C/C(=O)C1=NC=CN=C1.[N+](=O)(O)[O-].C(C)OC(C1=CC(=C(C=C1)C)NC(=N)N)=O>>C(C)OC(C1=CC(=C(C=C1)C)NC1=NC=CC(=N1)C1=NC=CN=C1)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH3:10])[c:11]([NH:12][C:13](=[NH:14])[NH2:24])[cH:25]1.CN(C)/[CH:15]=[CH:16]/[C:17](=O)[c:18]1[cH:19][n:20][cH:21][cH:22][n:23]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([CH3:10])[c:11]([NH:12][c:13]2[n:14][cH:15][cH:16][c:17](-[c:18]3[cH:19][n:2... | CCOC(=O)c1ccc(C)c(NC(=N)N)c1.CN(C)/C=C/C(=O)c1cnccn1 | CCOC(=O)c1ccc(C)c(Nc2nccc(-c3cnccn3)n2)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 78274536798da2b99a51ce47d0994df99b4d5455af910301779a9ae5938608b5 | 11da551d0a7bf93f6d300d0e461ec1d4a2060497908163f95323146dc93cd499 | c1ccc(Nc2nccc(-c3cnccn3)n2)cc1 | C-N(-C)/[CH;D2;+0:1]=[CH;D2;+0:2]/[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4]1:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:1.[NH2;D1;+0:10]-[C;H0;D3;+0:11](=[NH;D1;+0:12])-[#7:13]-[c:14]>>[c:14]-[#7:13]-[c;H0;D3;+0:11]1:[n;H0;D2;+0:12]:[cH;D2;+0:1]:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[c;H0;D3;+0:4]2:[#7;a:5]:[c:6]:[c:7]:[#7;a:8]:[c:9]:2):[n;H0... | null | [] | null | null | null | null | 3-dimethylamino-1-pyrazin-2-yl-propenone prepared in Preparation 2 and 3-guanidino-4-methylbenzoic acid ethyl ester nitrate were used instead 3-dimethylamino-1-pyridin-3-yl-propenone and 4-guanidino-benzoic acid ethyl ester nitrate according to the similar procedure to Preparation 8 to give the titled compound as yello... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Ketone.Primary amine | null | null | c1cncnc1 | c1ccccc1.c1cncnc1.c1cnccn1 | HO- | null | null | null | CCOC(=O)c1ccc(C)c(NC(=N)N)c1.CN(C)/C=C/C(=O)c1cnccn1>>CCOC(=O)c1ccc(C)c(Nc2nccc(-c3cnccn3)n2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c82f585d2f7478fbe681854b1c2d9de | CCOC(=O)c1ccc(Nc2nccc(-c3cccnc3)n2)cc1>>O=C(O)c1ccc(Nc2nccc(-c3cccnc3)n2)cc1 | C(C)OC(C1=CC=C(C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1)=O.[OH-].[Na+].O.Cl>>N1=CC(=CC=C1)C1=NC(=NC=C1)NC1=CC=C(C(=O)O)C=C1 | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][n:18][cH:19]3)[n:20]2)[cH:21][cH:22]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][cH:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][n:18][cH:19]3)[n:20]2)[cH:21][cH:22]1 | CCOC(=O)c1ccc(Nc2nccc(-c3cccnc3)n2)cc1 | O=C(O)c1ccc(Nc2nccc(-c3cccnc3)n2)cc1 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nccc(-c3cccnc3)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | 4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester prepared in Preparation 8 (19.6 g, 59.6 mmole) and 2N-sodium hydroxide (190 ml) were added to a reaction vessel under the solvent of water (190 ml) and ethanol (190 ml), mixed under reflux and cooled to RT, and pH thereof was adjusted to 1˜2 with hydrochlo... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1ccncc1 | Other | C(C)O | null | null | CCOC(=O)c1ccc(Nc2nccc(-c3cccnc3)n2)cc1>C(C)O>O=C(O)c1ccc(Nc2nccc(-c3cccnc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1f5c71da940c4f679c6f2c868399b31d | CCOC(=O)c1ccc(Nc2nccc(-c3nccs3)n2)cc1>>O=C(O)c1ccc(Nc2nccc(-c3nccs3)n2)cc1 | C(C)OC(C1=CC=C(C=C1)NC1=NC=CC(=N1)C=1SC=CN1)=O.C(C)OC(C1=CC=C(C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1)=O>>S1C(=NC=C1)C1=NC(=NC=C1)NC1=CC=C(C(=O)O)C=C1 | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][cH:12][c:13](-[c:14]3[n:15][cH:16][cH:17][s:18]3)[n:19]2)[cH:20][cH:21]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][cH:12][c:13](-[c:14]3[n:15][cH:16][cH:17][s:18]3)[n:19]2)[cH:20][cH:21]1 | CCOC(=O)c1ccc(Nc2nccc(-c3nccs3)n2)cc1 | O=C(O)c1ccc(Nc2nccc(-c3nccs3)n2)cc1 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nccc(-c3nccs3)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | 4-(4-thiazol-2-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester prepared in Preparation 9 was used instead of 4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester according to the similar procedure to Preparation 19 to give the titled compound as yellow solid.
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1cscn1 | Other | null | null | null | CCOC(=O)c1ccc(Nc2nccc(-c3nccs3)n2)cc1>>O=C(O)c1ccc(Nc2nccc(-c3nccs3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b2b992e896c44b4787143c64e46ecb7b | CCOC(=O)c1ccc(C)c(Nc2nccc(-c3nccs3)n2)c1>>Cc1ccc(C(=O)O)cc1Nc1nccc(-c2nccs2)n1 | C(C)OC(C1=CC(=C(C=C1)C)NC1=NC=CC(=N1)C=1SC=CN1)=O.C(C)OC(C1=CC=C(C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1)=O>>CC1=C(C=C(C(=O)O)C=C1)NC1=NC=CC(=N1)C=1SC=CN1 | CC[O:8][C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:10]([NH:11][c:12]2[n:13][cH:14][cH:15][c:16](-[c:17]3[n:18][cH:19][cH:20][s:21]3)[n:22]2)[cH:9]1)=[O:7]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][c:10]1[NH:11][c:12]1[n:13][cH:14][cH:15][c:16](-[c:17]2[n:18][cH:19][cH:20][s:21]2)[n:22]1 | CCOC(=O)c1ccc(C)c(Nc2nccc(-c3nccs3)n2)c1 | Cc1ccc(C(=O)O)cc1Nc1nccc(-c2nccs2)n1 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nccc(-c3nccs3)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | 4-methyl-3-(4-thiazol-2-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester prepared in Preparation 10 was used instead of 4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester according to the similar procedure to Preparation 19 to give the titled compound as yellow solid.
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1cscn1 | Other | null | null | null | CCOC(=O)c1ccc(C)c(Nc2nccc(-c3nccs3)n2)c1>>Cc1ccc(C(=O)O)cc1Nc1nccc(-c2nccs2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-24582fa9f41640f4aabdd175869c75e0 | CCOC(=O)c1ccc(C)c(Nc2nccc(-c3cnccn3)n2)c1>>Cc1ccc(C(=O)O)cc1Nc1nccc(-c2cnccn2)n1 | C(C)OC(C1=CC(=C(C=C1)C)NC1=NC=CC(=N1)C1=NC=CN=C1)=O.C(C)OC(C1=CC=C(C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1)=O>>CC1=C(C=C(C(=O)O)C=C1)NC1=NC=CC(=N1)C1=NC=CN=C1 | CC[O:8][C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:10]([NH:11][c:12]2[n:13][cH:14][cH:15][c:16](-[c:17]3[cH:18][n:19][cH:20][cH:21][n:22]3)[n:23]2)[cH:9]1)=[O:7]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][c:10]1[NH:11][c:12]1[n:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][n:19][cH:20][cH:21][n:22]2)[n:23]1 | CCOC(=O)c1ccc(C)c(Nc2nccc(-c3cnccn3)n2)c1 | Cc1ccc(C(=O)O)cc1Nc1nccc(-c2cnccn2)n1 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nccc(-c3cnccn3)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | 4-methyl-3-(4-pyrazin-2-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester prepared in Preparation 11 was used instead of 4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester according to the similar procedure to Preparation 19 to give the titled compound as yellow solid.
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1cnccn1 | Other | null | null | null | CCOC(=O)c1ccc(C)c(Nc2nccc(-c3cnccn3)n2)c1>>Cc1ccc(C(=O)O)cc1Nc1nccc(-c2cnccn2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-df29148af2df4c8f8dc6666d914c9252 | CCOC(=O)c1ccc(Nc2nccc(-c3cnccn3)n2)cc1>>O=C(O)c1ccc(Nc2nccc(-c3cnccn3)n2)cc1 | C(C)OC(C1=CC=C(C=C1)NC1=NC=CC(=N1)C1=NC=CN=C1)=O.C(C)OC(C1=CC=C(C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1)=O>>N1=C(C=NC=C1)C1=NC(=NC=C1)NC1=CC=C(C(=O)O)C=C1 | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][cH:12][c:13](-[c:14]3[cH:15][n:16][cH:17][cH:18][n:19]3)[n:20]2)[cH:21][cH:22]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][cH:12][c:13](-[c:14]3[cH:15][n:16][cH:17][cH:18][n:19]3)[n:20]2)[cH:21][cH:22]1 | CCOC(=O)c1ccc(Nc2nccc(-c3cnccn3)n2)cc1 | O=C(O)c1ccc(Nc2nccc(-c3cnccn3)n2)cc1 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nccc(-c3cnccn3)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | 4-(4-pyrazin-2-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester prepared in Preparation 12 was used instead of 4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester according to the similar procedure to Preparation 19 to give the titled compound as yellow solid.
Conditions: See reaction.notes.procedure_detail... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1cnccn1 | Other | null | null | null | CCOC(=O)c1ccc(Nc2nccc(-c3cnccn3)n2)cc1>>O=C(O)c1ccc(Nc2nccc(-c3cnccn3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1245f40d675a47ceb434cdcd2e539165 | CCOC(=O)c1ccc(C)c(Nc2nccc(-c3nccnc3C)n2)c1>>Cc1ccc(C(=O)O)cc1Nc1nccc(-c2nccnc2C)n1 | C(C)OC(C1=CC(=C(C=C1)C)NC1=NC=CC(=N1)C1=NC=CN=C1C)=O.C(C)OC(C1=CC=C(C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1)=O>>CC1=C(C=C(C(=O)O)C=C1)NC1=NC=CC(=N1)C1=NC=CN=C1C | CC[O:8][C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:10]([NH:11][c:12]2[n:13][cH:14][cH:15][c:16](-[c:17]3[n:18][cH:19][cH:20][n:21][c:22]3[CH3:23])[n:24]2)[cH:9]1)=[O:7]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][c:10]1[NH:11][c:12]1[n:13][cH:14][cH:15][c:16](-[c:17]2[n:18][cH:19][cH:20][n:21][c:22]2[CH3:23... | CCOC(=O)c1ccc(C)c(Nc2nccc(-c3nccnc3C)n2)c1 | Cc1ccc(C(=O)O)cc1Nc1nccc(-c2nccnc2C)n1 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nccc(-c3cnccn3)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | 4-methyl-3-[4-(3-methylpyrazin-2-yl)-pyrimidin-2-ylamino]-benzoic acid ethyl ester prepared in Preparation 13 was used instead of 4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester according to the similar procedure to Preparation 19 to give the titled compound as yellow solid.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1cnccn1 | Other | null | null | null | CCOC(=O)c1ccc(C)c(Nc2nccc(-c3nccnc3C)n2)c1>>Cc1ccc(C(=O)O)cc1Nc1nccc(-c2nccnc2C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-638da218e91b46e8a69f4efdbb435f4a | CCOC(=O)c1ccc(Nc2nccc(-c3nccnc3C)n2)cc1>>Cc1nccnc1-c1ccnc(Nc2ccc(C(=O)O)cc2)n1 | C(C)OC(C1=CC=C(C=C1)NC1=NC=CC(=N1)C1=NC=CN=C1C)=O.C(C)OC(C1=CC=C(C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1)=O>>CC=1C(=NC=CN1)C1=NC(=NC=C1)NC1=CC=C(C(=O)O)C=C1 | CC[O:20][C:18]([c:17]1[cH:16][cH:15][c:14]([NH:13][c:12]2[n:11][cH:10][cH:9][c:8](-[c:7]3[c:2]([CH3:1])[n:3][cH:4][cH:5][n:6]3)[n:23]2)[cH:22][cH:21]1)=[O:19]>>[CH3:1][c:2]1[n:3][cH:4][cH:5][n:6][c:7]1-[c:8]1[cH:9][cH:10][n:11][c:12]([NH:13][c:14]2[cH:15][cH:16][c:17]([C:18](=[O:19])[OH:20])[cH:21][cH:22]2)[n:23]1 | CCOC(=O)c1ccc(Nc2nccc(-c3nccnc3C)n2)cc1 | Cc1nccnc1-c1ccnc(Nc2ccc(C(=O)O)cc2)n1 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nccc(-c3cnccn3)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | 4-[4-(3-methylpyrazin-2-yl)-pyrimidin-2-ylamino]-benzoic acid ethyl ester prepared in Preparation 14 was used instead of 4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester according to the similar procedure to Preparation 19 to give the titled compound as yellow solid.
Conditions: See reaction.notes.proced... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cnccn1.c1cncnc1.c1ccccc1 | Other | null | null | null | CCOC(=O)c1ccc(Nc2nccc(-c3nccnc3C)n2)cc1>>Cc1nccnc1-c1ccnc(Nc2ccc(C(=O)O)cc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-01f82e3b9f2b4781b050a0f646eb76bd | CCOC(=O)c1ccc(C)c(Nc2nccc(Nc3nccs3)n2)c1>>Cc1ccc(C(=O)O)cc1Nc1nccc(Nc2nccs2)n1 | C(C)OC(C1=CC(=C(C=C1)C)NC1=NC=CC(=N1)NC=1SC=CN1)=O.C(C)OC(C1=CC=C(C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1)=O>>CC1=C(C=C(C(=O)O)C=C1)NC1=NC=CC(=N1)NC=1SC=CN1 | CC[O:8][C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:10]([NH:11][c:12]2[n:13][cH:14][cH:15][c:16]([NH:17][c:18]3[n:19][cH:20][cH:21][s:22]3)[n:23]2)[cH:9]1)=[O:7]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][c:10]1[NH:11][c:12]1[n:13][cH:14][cH:15][c:16]([NH:17][c:18]2[n:19][cH:20][cH:21][s:22]2)[n:23]1 | CCOC(=O)c1ccc(C)c(Nc2nccc(Nc3nccs3)n2)c1 | Cc1ccc(C(=O)O)cc1Nc1nccc(Nc2nccs2)n1 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nccc(Nc3nccs3)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | 4-methyl-3-[4-(thiazol-2-ylamino)-pyrimidin-2-ylamino]-benzoic acid ethyl ester prepared in Preparation 15 was used instead of 4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester according to the similar procedure to Preparation 19 to give the titled compound as yellow solid.
Conditions: See reaction.notes.... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1cscn1 | Other | null | null | null | CCOC(=O)c1ccc(C)c(Nc2nccc(Nc3nccs3)n2)c1>>Cc1ccc(C(=O)O)cc1Nc1nccc(Nc2nccs2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8c9b23c6a59349498e1b6178ffc413a0 | CCOC(=O)c1ccc(Nc2nccc(Nc3nccs3)n2)cc1>>O=C(O)c1ccc(Nc2nccc(Nc3nccs3)n2)cc1 | C(C)OC(C1=CC=C(C=C1)NC1=NC=CC(=N1)NC=1SC=CN1)=O.C(C)OC(C1=CC=C(C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1)=O>>S1C(=NC=C1)NC1=NC(=NC=C1)NC1=CC=C(C(=O)O)C=C1 | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][cH:12][c:13]([NH:14][c:15]3[n:16][cH:17][cH:18][s:19]3)[n:20]2)[cH:21][cH:22]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][cH:12][c:13]([NH:14][c:15]3[n:16][cH:17][cH:18][s:19]3)[n:20]2)[cH:21][cH:22]1 | CCOC(=O)c1ccc(Nc2nccc(Nc3nccs3)n2)cc1 | O=C(O)c1ccc(Nc2nccc(Nc3nccs3)n2)cc1 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nccc(Nc3nccs3)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | 4-[4-(thiazol-2-ylamino)-pyrimidin-2-ylamino]-benzoic acid ethyl ester prepared in Preparation 16 was used instead of 4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester according to the similar procedure to Preparation 19 to give the titled compound as yellow solid.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1cscn1 | Other | null | null | null | CCOC(=O)c1ccc(Nc2nccc(Nc3nccs3)n2)cc1>>O=C(O)c1ccc(Nc2nccc(Nc3nccs3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-90937b088d3d4aa2bbcc9ba53a79bd37 | CCOC(=O)c1ccc(C)c(Nc2nccc(-n3ccnc3)n2)c1>>Cc1ccc(C(=O)O)cc1Nc1nccc(-n2ccnc2)n1 | C(C)OC(C1=CC(=C(C=C1)C)NC1=NC=CC(=N1)N1C=NC=C1)=O.C(C)OC(C1=CC=C(C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1)=O>>N1(C=NC=C1)C1=NC(=NC=C1)NC=1C=C(C(=O)O)C=CC1C | CC[O:8][C:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[c:10]([NH:11][c:12]2[n:13][cH:14][cH:15][c:16](-[n:17]3[cH:18][cH:19][n:20][cH:21]3)[n:22]2)[cH:9]1)=[O:7]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][c:10]1[NH:11][c:12]1[n:13][cH:14][cH:15][c:16](-[n:17]2[cH:18][cH:19][n:20][cH:21]2)[n:22]1 | CCOC(=O)c1ccc(C)c(Nc2nccc(-n3ccnc3)n2)c1 | Cc1ccc(C(=O)O)cc1Nc1nccc(-n2ccnc2)n1 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nccc(-n3ccnc3)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | 3-(4-imidazol-1-yl-pyrimidin-2-ylamino)-4-methylbenzoic acid ethyl ester prepared in Preparation 17 was used instead of 4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester according to the similar procedure to Preparation 19 to give the titled compound as yellow solid.
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1c[nH]cn1 | Other | null | null | null | CCOC(=O)c1ccc(C)c(Nc2nccc(-n3ccnc3)n2)c1>>Cc1ccc(C(=O)O)cc1Nc1nccc(-n2ccnc2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-51a3d71ca96b41e8914a5e67d368745b | CCOC(=O)c1ccc(Nc2nccc(-n3ccnc3)n2)cc1>>O=C(O)c1ccc(Nc2nccc(-n3ccnc3)n2)cc1 | C(C)OC(C1=CC=C(C=C1)NC1=NC=CC(=N1)N1C=NC=C1)=O.C(C)OC(C1=CC=C(C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1)=O>>N1(C=NC=C1)C1=NC(=NC=C1)NC1=CC=C(C(=O)O)C=C1 | CC[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][cH:12][c:13](-[n:14]3[cH:15][cH:16][n:17][cH:18]3)[n:19]2)[cH:20][cH:21]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][c:7]([NH:8][c:9]2[n:10][cH:11][cH:12][c:13](-[n:14]3[cH:15][cH:16][n:17][cH:18]3)[n:19]2)[cH:20][cH:21]1 | CCOC(=O)c1ccc(Nc2nccc(-n3ccnc3)n2)cc1 | O=C(O)c1ccc(Nc2nccc(-n3ccnc3)n2)cc1 | null | null | null | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Nc2nccc(-n3ccnc3)n2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | 4-(4-imidazol-1-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester prepared in Preparation 18 was used instead of 4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid ethyl ester according to the similar procedure to Preparation 19 to give the titled compound as yellow solid.
Conditions: See reaction.notes.procedure_detai... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cncnc1.c1c[nH]cn1 | Other | null | null | null | CCOC(=O)c1ccc(Nc2nccc(-n3ccnc3)n2)cc1>>O=C(O)c1ccc(Nc2nccc(-n3ccnc3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2a51e84d22ac42abaf14a4270c721b0e | Cc1c[nH]cn1.Nc1cc(Br)cc(C(F)(F)F)c1>>Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1 | NC=1C=C(C=C(C1)Br)C(F)(F)F.CC=1N=CNC1.C([O-])([O-])=O.[K+].[K+].CN(C(C)=O)C>>CC=1N=CN(C1)C=1C=C(C=C(C1)C(F)(F)F)N | [CH3:1][c:2]1[cH:3][nH:4][cH:16][n:17]1.Br[c:5]1[cH:6][c:7]([NH2:8])[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]1>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][c:7]([NH2:8])[cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15]2)[cH:16][n:17]1 | Cc1c[nH]cn1.Nc1cc(Br)cc(C(F)(F)F)c1 | Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | b282a5e1885a37e36f5b39b22cb06585a64583e50efbafa1ce368e9c3dbc55f3 | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc(-n2ccnc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[nH;D2;+0:10]:[c:11]:1>>[C;D1;H3:6]-[c:7]1:[#7;a:8]:[c:9]:[n;H0;D3;+0:10](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:11]:1 | null | [] | null | null | 16 | HOUR | 3-amino-5-bromo-benzotrifluoride (17.1 g, 71.24 mmol), 4-methylimidazole (17.6 g, 213.72 mmol), potassium carbonate (9.8 g, 71.24 mmol), cupper (1.1 g, 17.81 mmol), and cupper iode (II) (3.4 g, 17.81 mmol) were added to N,N-dimethylacetamide (100 ml) at room temperature, and mixed therewith at 140˜150° C. for 16 hr. Af... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | c1c[nH]cn1.c1ccccc1 | HBr | C(C)(=O)OCC | null | 16 | Cc1c[nH]cn1.Nc1cc(Br)cc(C(F)(F)F)c1>C(C)(=O)OCC>Cc1cn(-c2cc(N)cc(C(F)(F)F)c2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8acb759fb58643299db5704f732afdcc | Cc1nccn1-c1cc(N)cc(C(F)(F)F)c1.O=C(O)c1ccc(Nc2nccc(-c3cccnc3)n2)cc1>>Cc1nccn1-c1cc(NC(=O)c2ccc(Nc3nccc(-c4cccnc4)n3)cc2)cc(C(F)(F)F)c1 | CC=1N(C=CN1)C=1C=C(C=C(C1)C(F)(F)F)N.CC=1N=CN(C1)C=1C=C(C=C(C1)C(F)(F)F)N.N1=CC(=CC=C1)C1=NC(=NC=C1)NC1=CC=C(C(=O)O)C=C1>>CC=1N(C=CN1)C=1C=C(C=C(C1)C(F)(F)F)NC(C1=CC=C(C=C1)NC1=NC=CC(=N1)C=1C=NC=CC1)=O | [CH3:1][c:2]1[n:3][cH:4][cH:5][n:6]1-[c:7]1[cH:8][c:9]([NH2:10])[cH:32][c:33]([C:34]([F:35])([F:36])[F:37])[cH:38]1.O[C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([NH:17][c:18]2[n:19][cH:20][cH:21][c:22](-[c:23]3[cH:24][cH:25][cH:26][n:27][cH:28]3)[n:29]2)[cH:30][cH:31]1>>[CH3:1][c:2]1[n:3][cH:4][cH:5][n:6]1-[c:7]1[cH:8][... | Cc1nccn1-c1cc(N)cc(C(F)(F)F)c1.O=C(O)c1ccc(Nc2nccc(-c3cccnc3)n2)cc1 | Cc1nccn1-c1cc(NC(=O)c2ccc(Nc3nccc(-c4cccnc4)n3)cc2)cc(C(F)(F)F)c1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccc(-n2ccnc2)c1)c1ccc(Nc2nccc(-c3cccnc3)n2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 3-(2-methyl-imidazol-1-yl)-5 -trifluoromethyl-phenylamine prepared in Preparation 31 was used instead of 3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-phenylamine and 4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid prepared in Preparation 19 according to the similar procedure to Example 1 to give the titled compound... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ncc[nH]1.c1ccccc1.c1ccccc1.c1cncnc1.c1ccncc1 | HO- | null | null | null | Cc1nccn1-c1cc(N)cc(C(F)(F)F)c1.O=C(O)c1ccc(Nc2nccc(-c3cccnc3)n2)cc1>>Cc1nccn1-c1cc(NC(=O)c2ccc(Nc3nccc(-c4cccnc4)n3)cc2)cc(C(F)(F)F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0a2a9a95fff14f20b484445298ab6fc0 | Cc1ccc(C(=O)O)cc1Nc1nccc(-c2nccs2)n1.Cc1cnc(N)s1>>Cc1cnc(NC(=O)c2ccc(C)c(Nc3nccc(-c4nccs4)n3)c2)s1 | CC=1N=CN(C1)C=1C=C(C=C(C1)C(F)(F)F)N.CC1=C(C=C(C(=O)O)C=C1)NC1=NC=CC(=N1)C=1SC=CN1.NC=1SC(=CN1)C.N1=CC(=CC=C1)C1=NC(=NC=C1)NC1=CC=C(C(=O)O)C=C1>>CC1=C(C=C(C(=O)NC=2SC(=CN2)C)C=C1)NC1=NC=CC(=N1)C=1SC=CN1 | O[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([CH3:13])[c:14]([NH:15][c:16]2[n:17][cH:18][cH:19][c:20](-[c:21]3[n:22][cH:23][cH:24][s:25]3)[n:26]2)[cH:27]1.[CH3:1][c:2]1[cH:3][n:4][c:5]([NH2:6])[s:28]1>>[CH3:1][c:2]1[cH:3][n:4][c:5]([NH:6][C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]([CH3:13])[c:14]([NH:15][c:16]3[n:17][cH:18][cH... | Cc1ccc(C(=O)O)cc1Nc1nccc(-c2nccs2)n1.Cc1cnc(N)s1 | Cc1cnc(NC(=O)c2ccc(C)c(Nc3nccc(-c4nccs4)n3)c2)s1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1nccs1)c1cccc(Nc2nccc(-c3nccs3)n2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[#16;a:8]:[c:9]:[c:10]:[#7;a:11]:1)-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 4-methyl-3-(4-thiazol-2-yl-pyrimidin-2-ylamino)-benzoic acid and 2-amino-5-methylthiazole were used instead of 4-(4-pyridin-3-yl-pyrimidin-2-ylamino)-benzoic acid and 3-(4-methylimidazol-1-yl)-5-trifluoromethyl-phenylamine according to the similar procedure to Example 5 to give the titled compound as yellow brown solid... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cscn1.c1ccccc1.c1cncnc1.c1cscn1 | HO- | null | null | null | Cc1ccc(C(=O)O)cc1Nc1nccc(-c2nccs2)n1.Cc1cnc(N)s1>>Cc1cnc(NC(=O)c2ccc(C)c(Nc3nccc(-c4nccs4)n3)c2)s1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-25707edd76fc43a589cfa82a58fed9c7 | Cc1cn(-c2ccnc(Nc3cc(C(=O)O)ccc3C)n2)cn1.Cc1nccn1-c1cc(N)cc(C(F)(F)F)c1>>Cc1cn(-c2ccnc(Nc3cc(C(=O)Nc4cc(-n5ccnc5C)cc(C(F)(F)F)c4)ccc3C)n2)cn1 | CC1=C(C=C(C(=O)O)C=C1)NC1=NC=CC(=N1)N1C=NC(=C1)C.CC=1N(C=CN1)C=1C=C(C=C(C1)C(F)(F)F)N>>CC1=C(C=C(C(=O)NC2=CC(=CC(=C2)C(F)(F)F)N2C(=NC=C2)C)C=C1)NC1=NC=CC(=N1)N1C=NC(=C1)C | O[C:14]([c:13]1[cH:12][c:11]([NH:10][c:9]2[n:8][cH:7][cH:6][c:5](-[n:4]3[cH:3][c:2]([CH3:1])[n:39][cH:38]3)[n:37]2)[c:35]([CH3:36])[cH:34][cH:33]1)=[O:15].[NH2:16][c:17]1[cH:18][c:19](-[n:20]2[cH:21][cH:22][n:23][c:24]2[CH3:25])[cH:26][c:27]([C:28]([F:29])([F:30])[F:31])[cH:32]1>>[CH3:1][c:2]1[cH:3][n:4](-[c:5]2[cH:6][... | Cc1cn(-c2ccnc(Nc3cc(C(=O)O)ccc3C)n2)cn1.Cc1nccn1-c1cc(N)cc(C(F)(F)F)c1 | Cc1cn(-c2ccnc(Nc3cc(C(=O)Nc4cc(-n5ccnc5C)cc(C(F)(F)F)c4)ccc3C)n2)cn1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cccc(-n2ccnc2)c1)c1cccc(Nc2nccc(-n3ccnc3)n2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 4-methyl-3-[4-(4-methylimidazol-1-yl)pyrimidin-2-yl-amino]benzoic acid and 3-(2-methylimidazol-1-yl)-5-trifluoromethyl-phenylamine prepared in Preparation 31 were used according to the similar procedure to Example 1 to give the titled compound as yellow solid.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1c[nH]cn1.c1cncnc1.c1ccccc1.c1ccccc1.c1ncc[nH]1 | HO- | null | null | null | Cc1cn(-c2ccnc(Nc3cc(C(=O)O)ccc3C)n2)cn1.Cc1nccn1-c1cc(N)cc(C(F)(F)F)c1>>Cc1cn(-c2ccnc(Nc3cc(C(=O)Nc4cc(-n5ccnc5C)cc(C(F)(F)F)c4)ccc3C)n2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b48f535d7fd94fe4abb81e3ef75e2c78 | Cc1ccc(S(=O)(=O)OC2CC(C(=O)N3CCN(c4ccccc4C#N)CC3)N(C(=O)OC(C)(C)C)C2)cc1.c1ccc(-c2nnn[nH]2)cc1>>COC(=O)C1CC(n2nnc(-c3ccccc3)n2)CN1C(=O)OC(C)(C)C | C1(=CC=CC=C1)C1=NN=NN1.C(C)(C)(C)OC(=O)N1C(CC(C1)OS(=O)(=O)C1=CC=C(C=C1)C)C(=O)N1CCN(CC1)C1=C(C=CC=C1)C#N.C([O-])([O-])=O.[Na+].[Na+]>>COC(=O)C1N(CC(C1)N1N=C(N=N1)C1=CC=CC=C1)C(=O)OC(C)(C)C | Cc1ccc(S(=O)(=O)O[CH:7]2[CH2:6][CH:5]([C:3](N3CCN(c4ccccc4C#N)CC3)=[O:4])[N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:19]2)cc1.[nH:8]1[n:9][n:10][n:18][c:11]1-[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH2:6][CH:7]([n:8]2[n:9][n:10][c:11](-[c:12]3[cH:13][cH:14][... | Cc1ccc(S(=O)(=O)OC2CC(C(=O)N3CCN(c4ccccc4C#N)CC3)N(C(=O)OC(C)(C)C)C2)cc1.c1ccc(-c2nnn[nH]2)cc1 | COC(=O)C1CC(n2nnc(-c3ccccc3)n2)CN1C(=O)OC(C)(C)C | null | null | CC(OCC)=O.CN(C)C=O | Acylation | OtherReaction | 30091fa135662be08093f47f39f1892b50e122f0d4e91644a08f61b7b51fb2d2 | 5a9de951c51d329c4e8327fcecf98d443b92554ca385afdc1b7ed444c7914b33 | c1ccc(-c2nnn(C3CCNC3)n2)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH;D3;+0:1]2-[C:2]-[#7:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[C:11](-[C;H0;D3;+0:12](=[O;D1;H0:13])-N3-C-C-N(-c4:c:c:c:c:c:4-C#N)-C-C-3)-[C:14]-2):c:c:1.[c:15]:[c:16](-[c;H0;D3;+0:17]1:[n;H0;D2;+0:18]:[n;H0;D2;+0:19]:[#7;a:20]:[nH;D2;+0:21]:1):[c:22]>>[C... | null | [] | null | null | 8 | HOUR | To a solution of a corresponding phenyl-tetrazole in DMF is added 2-[4-(2-cyano-phenyl)-piperazine-1-carbonyl]-4-(toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester and anhydrous sodium carbonate. The mixture is stirred at about 60 degree overnight. The solution is diluted with EA, washed, dried and ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Nitrile.Tertiary amide.Tertiary amine | Ester | c1ccccc1.C1CC[NH]C1.C1CNCCN1.c1ccccc1.c1nnn[nH]1 | C1CC[NH]C1.c1nnn[nH]1 | C1CC[NH]C1.c1nnn[nH]1.c1ccccc1 | TsOH.HO- | CC(OCC)=O.CN(C)C=O | null | 8 | Cc1ccc(S(=O)(=O)OC2CC(C(=O)N3CCN(c4ccccc4C#N)CC3)N(C(=O)OC(C)(C)C)C2)cc1.c1ccc(-c2nnn[nH]2)cc1>CC(OCC)=O.CN(C)C=O>COC(=O)C1CC(n2nnc(-c3ccccc3)n2)CN1C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e7b0ae02522245aa92fb381a63fa066a | COC(=O)C1CC(n2nnc(-c3ccccc3)n2)CN1C(=O)OC(C)(C)C>>CC(C)(C)OC(=O)N1CC(n2nnc(-c3ccccc3)n2)CC1C(=O)O | COC(=O)C1N(CC(C1)N1N=C(N=N1)C1=CC=CC=C1)C(=O)OC(C)(C)C.[Li+].[OH-]>>C(C)(C)(C)OC(=O)N1C(CC(C1)N1N=C(N=N1)C1=CC=CC=C1)C(=O)O | C[O:26][C:24]([CH:23]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH:10]([n:11]2[n:12][n:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[n:21]2)[CH2:22]1)=[O:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH:10]([n:11]2[n:12][n:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19... | COC(=O)C1CC(n2nnc(-c3ccccc3)n2)CN1C(=O)OC(C)(C)C | CC(C)(C)OC(=O)N1CC(n2nnc(-c3ccccc3)n2)CC1C(=O)O | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2nnn(C3CCNC3)n2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | null | [] | null | null | 8 | HOUR | To a solution of 4-[5-(phenyl)-tetrazol-2-yl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (4) in MeOH cooled to 0 degree is LiOH, and the mixture is stirred overnight. After removal of MeOH, the residue is acidified with HCl, extracted with EA, dried and concentrated to give the corresponding 4-... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]C1.c1nnn[nH]1.c1ccccc1 | Other | CO | null | 8 | COC(=O)C1CC(n2nnc(-c3ccccc3)n2)CN1C(=O)OC(C)(C)C>CO>CC(C)(C)OC(=O)N1CC(n2nnc(-c3ccccc3)n2)CC1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a2b57657d7144f9e9ef581aa8916d813 | CC(C)(C)OC(=O)N1CC(n2nnc(-c3ccccc3)n2)CC1C(=O)N1CCN(c2ccccc2C#N)CC1>>N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccccc4)n3)CN2)CC1 | C(C)(C)(C)OC(=O)N1C(CC(C1)N1N=C(N=N1)C1=CC=CC=C1)C(=O)N1CCN(CC1)C1=C(C=CC=C1)C#N.C(=O)(C(F)(F)F)O>>C1(=CC=CC=C1)C=1N=NN(N1)C1CC(NC1)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1 | CC(C)(C)OC(=O)[N:30]1[CH:15]([C:13]([N:12]2[CH2:11][CH2:10][N:9]([c:8]3[c:3]([C:2]#[N:1])[cH:4][cH:5][cH:6][cH:7]3)[CH2:32][CH2:31]2)=[O:14])[CH2:16][CH:17]([n:18]2[n:19][n:20][c:21](-[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[n:28]2)[CH2:29]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:1... | CC(C)(C)OC(=O)N1CC(n2nnc(-c3ccccc3)n2)CC1C(=O)N1CCN(c2ccccc2C#N)CC1 | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccccc4)n3)CN2)CC1 | null | null | null | Reduction | Boc amine deprotection | 7b506000be0005f6be41b2386b5bd6a8c45f704baa22d692d2f2ec984758e4ad | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(C1CC(n2nnc(-c3ccccc3)n2)CN1)N1CCN(c2ccccc2)CC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1-[C:6](=[O;D1;H0:7])-[#7:8](-[C:9])-[C:10]>>[C:9]-[#7:8](-[C:6](=[O;D1;H0:7])-[C:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1)-[C:10] | null | [] | null | null | 5 | HOUR | 2-[4-(2-Cyano-phenyl)-piperazine-1-carbonyl]-4-[5-(phenyl)-tetrazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (6) is added to CF3COOH, and the reaction mixture is stirred for about 5 h. After removal of CF3COOH, the residue is dissolved in DCM, washed, dried and concentrated to give 2-(4-{4-[5-(phenyl)-tetra... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | c1ccccc1.C1C[NH]CC[NH]1.C1CCNC1.c1nnn[nH]1.c1ccccc1 | HO- | null | null | 5 | CC(C)(C)OC(=O)N1CC(n2nnc(-c3ccccc3)n2)CC1C(=O)N1CCN(c2ccccc2C#N)CC1>>N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccccc4)n3)CN2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea3e139e0a46420c876caf56eeffaa82 | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccccc4)n3)CN2)CC1.O=Cc1ccccc1>>N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccccc4)n3)CN2Cc2ccccc2)CC1 | [BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].C1(=CC=CC=C1)C=1N=NN(N1)C1CC(NC1)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1.C(C1=CC=CC=C1)=O.C(C)(=O)O>>C(C1=CC=CC=C1)N1C(CC(C1)N1N=C(N=N1)C1=CC=CC=C1)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH:15]2[CH2:16][CH:17]([n:18]3[n:19][n:20][c:21](-[c:22]4[cH:23][cH:24][cH:25][cH:26][cH:27]4)[n:28]3)[CH2:29][NH:30]2)[CH2:38][CH2:39]1.O=[CH:31][c:32]1[cH:33][cH:34][cH:35][cH:36][cH:37]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][c... | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccccc4)n3)CN2)CC1.O=Cc1ccccc1 | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccccc4)n3)CN2Cc2ccccc2)CC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | reductive amination | f320c54beea598cd731a01400cf9495fa26416685f3307ec69cb487e38cf79c3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C(C1CC(n2nnc(-c3ccccc3)n2)CN1Cc1ccccc1)N1CCN(c2ccccc2)CC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[C:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1)-[C:14]>>[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[C:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:14] | null | [] | null | null | 20 | MINUTE | 2-(4-{4-[5-(Phenyl)-tetrazol-2-yl]-pyrrolidine-2-carbonyl}-piperazin-1-yl)-benzonitrile (2), benzaldehyde and acetic acid (cat) is dissolved in DCM and the solution is stirred for 20 min. Then NaBH(OAc)3 is added. The resulting mixture is warmed to r.t and stirred overnight. The solution is then washed with sat NaHCO3,... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1C[NH]CC[NH]1.C1CC[NH]C1.c1nnn[nH]1.c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | null | 0.333333 | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccccc4)n3)CN2)CC1.O=Cc1ccccc1>C(Cl)Cl>N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccccc4)n3)CN2Cc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-96039615c0384ebc918f9beb2e65bb35 | Cc1ccc(S(=O)(=O)O[C@@H]2C[C@@H](C(=O)N3CCN(c4ccccc4C#N)CC3)N(C(=O)OC(C)(C)C)C2)cc1.Fc1ccc(-c2nnn[nH]2)c(F)c1>>COC(=O)[C@@H]1C[C@H](n2nnc(-c3ccc(F)cc3F)n2)CN1C(=O)OC(C)(C)C | FC1=C(C=CC(=C1)F)C1=NN=NN1.C(C)(C)(C)OC(=O)N1[C@@H](C[C@H](C1)OS(=O)(=O)C1=CC=C(C=C1)C)C(=O)N1CCN(CC1)C1=C(C=CC=C1)C#N.C([O-])([O-])=O.[Na+].[Na+]>>COC(=O)[C@H]1N(C[C@H](C1)N1N=C(N=N1)C1=C(C=C(C=C1)F)F)C(=O)OC(C)(C)C | Cc1ccc(S(=O)(=O)O[C@@H:7]2[CH2:6][C@@H:5]([C:3](N3CCN(c4ccccc4C#N)CC3)=[O:4])[N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:21]2)cc1.[nH:8]1[n:9][n:10][n:20][c:11]1-[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][c:18]1[F:19]>>[CH3:1][O:2][C:3](=[O:4])[C@@H:5]1[CH2:6][C@H:7]([n:8]2[n:9][n:10][c:11](-[c:... | Cc1ccc(S(=O)(=O)O[C@@H]2C[C@@H](C(=O)N3CCN(c4ccccc4C#N)CC3)N(C(=O)OC(C)(C)C)C2)cc1.Fc1ccc(-c2nnn[nH]2)c(F)c1 | COC(=O)[C@@H]1C[C@H](n2nnc(-c3ccc(F)cc3F)n2)CN1C(=O)OC(C)(C)C | null | null | CC(OCC)=O.CN(C)C=O | Acylation | OtherReaction | 30091fa135662be08093f47f39f1892b50e122f0d4e91644a08f61b7b51fb2d2 | 5a9de951c51d329c4e8327fcecf98d443b92554ca385afdc1b7ed444c7914b33 | c1ccc(-c2nnn([C@H]3CCNC3)n2)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[C@H;D3;+0:1]2-[C:2]-[#7:3](-[C:4](=[O;D1;H0:5])-[#8:6]-[C:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10])-[C:11](-[C;H0;D3;+0:12](=[O;D1;H0:13])-N3-C-C-N(-c4:c:c:c:c:c:4-C#N)-C-C-3)-[C:14]-2):c:c:1.[c:15]:[c:16](-[c;H0;D3;+0:17]1:[n;H0;D2;+0:18]:[n;H0;D2;+0:19]:[#7;a:20]:[nH;D2;+0:21]:1):[c:22]>>[... | 61.8 | [{"value": 61.8, "product": "COC(=O)[C@H]1N(C[C@H](C1)N1N=C(N=N1)C1=C(C=C(C=C1)F)F)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of (2,4-difluoro-phenyl)-tetrazole (0.44 g, 1.1 mmol) in 5 ml DMF was added 0.1 g (0.55 mmol) of (2S,4R)-2-[4-(2-cyano-phenyl)-piperazine-1-carbonyl]-4-(toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester and anhydrous sodium carbonate (0.15 g, 1.4 mmol). The mixture was stirred vigorous... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Nitrile.Tertiary amide.Tertiary amine | Ester | c1ccccc1.C1CC[NH]C1.C1CNCCN1.c1ccccc1.c1nnn[nH]1 | C1CC[NH]C1.c1nnn[nH]1 | C1CC[NH]C1.c1nnn[nH]1.c1ccccc1 | TsOH.HO- | CC(OCC)=O.CN(C)C=O | null | 8 | Cc1ccc(S(=O)(=O)O[C@@H]2C[C@@H](C(=O)N3CCN(c4ccccc4C#N)CC3)N(C(=O)OC(C)(C)C)C2)cc1.Fc1ccc(-c2nnn[nH]2)c(F)c1>CC(OCC)=O.CN(C)C=O>COC(=O)[C@@H]1C[C@H](n2nnc(-c3ccc(F)cc3F)n2)CN1C(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-982829d1b8824b38806b2ebcd6513025 | COC(=O)C1CC(n2nnc(-c3ccc(F)cc3F)n2)CN1C(=O)OC(C)(C)C>>CC(C)(C)OC(=O)N1C[C@@H](n2nnc(-c3ccc(F)cc3F)n2)C[C@H]1C(=O)O | COC(=O)C1N(CC(C1)N1N=C(N=N1)C1=C(C=C(C=C1)F)F)C(=O)OC(C)(C)C.[Li+].[OH-]>>C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N1N=C(N=N1)C1=C(C=C(C=C1)F)F)C(=O)O | C[O:28][C:26]([CH:25]1[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH:10]([n:11]2[n:12][n:13][c:14](-[c:15]3[cH:16][cH:17][c:18]([F:19])[cH:20][c:21]3[F:22])[n:23]2)[CH2:24]1)=[O:27]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][C@@H:10]([n:11]2[n:12][n:13][c:14](-[c:15]3[cH:16][cH:17... | COC(=O)C1CC(n2nnc(-c3ccc(F)cc3F)n2)CN1C(=O)OC(C)(C)C | CC(C)(C)OC(=O)N1C[C@@H](n2nnc(-c3ccc(F)cc3F)n2)C[C@H]1C(=O)O | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2nnn([C@H]3CCNC3)n2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[#7:5]>>[#7:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 73.5 | [{"value": 73.5, "product": "C(C)(C)(C)OC(=O)N1[C@@H](C[C@@H](C1)N1N=C(N=N1)C1=C(C=C(C=C1)F)F)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 4-[5-(2,4-difluoro-phenyl)-tetrazol-2-yl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (0.14 g, 0.34 mmol) in MeOH (25 ml) cooled to 0 degree was added LiOH (0.06 g, 1.36 mmol), and the mixture was stirred overnight. After removal of MeOH, the residue was acidified with 2M HCl. T... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]C1.c1nnn[nH]1.c1ccccc1 | Other | CO | null | 8 | COC(=O)C1CC(n2nnc(-c3ccc(F)cc3F)n2)CN1C(=O)OC(C)(C)C>CO>CC(C)(C)OC(=O)N1C[C@@H](n2nnc(-c3ccc(F)cc3F)n2)C[C@H]1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f3642393ee714bab8666b06f2f772200 | CC(C)(C)OC(=O)N1CC(n2nnc(-c3ccc(F)cc3F)n2)CC1C(=O)N1CCN(c2ccccc2C#N)CC1>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1 | C(C)(C)(C)OC(=O)N1C(CC(C1)N1N=C(N=N1)C1=C(C=C(C=C1)F)F)C(=O)N1CCN(CC1)C1=C(C=CC=C1)C#N.C(=O)(C(F)(F)F)O>>FC1=C(C=CC(=C1)F)C=1N=NN(N1)[C@H]1C[C@H](NC1)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1 | CC(C)(C)OC(=O)[N:32]1[CH:15]([C:13]([N:12]2[CH2:11][CH2:10][N:9]([c:8]3[c:3]([C:2]#[N:1])[cH:4][cH:5][cH:6][cH:7]3)[CH2:34][CH2:33]2)=[O:14])[CH2:16][CH:17]([n:18]2[n:19][n:20][c:21](-[c:22]3[cH:23][cH:24][c:25]([F:26])[cH:27][c:28]3[F:29])[n:30]2)[CH2:31]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10]... | CC(C)(C)OC(=O)N1CC(n2nnc(-c3ccc(F)cc3F)n2)CC1C(=O)N1CCN(c2ccccc2C#N)CC1 | N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1 | null | null | null | Reduction | Boc amine deprotection | 7b506000be0005f6be41b2386b5bd6a8c45f704baa22d692d2f2ec984758e4ad | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C([C@@H]1C[C@H](n2nnc(-c3ccccc3)n2)CN1)N1CCN(c2ccccc2)CC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[CH;D3;+0:5]-1-[C:6](=[O;D1;H0:7])-[#7:8](-[C:9])-[C:10]>>[C:9]-[#7:8](-[C:6](=[O;D1;H0:7])-[C@@H;D3;+0:5]1-[C:4]-[C:3]-[C:2]-[NH;D2;+0:1]-1)-[C:10] | 87.9 | [{"value": 87.9, "product": "FC1=C(C=CC(=C1)F)C=1N=NN(N1)[C@H]1C[C@H](NC1)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | 2-[4-(2-Cyano-phenyl)-piperazine-1-carbonyl]-4-[5-(2,4-difluoro-phenyl)-tetrazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.184 g, 0.33 mmol) was added to CF3COOH (0.22 g, 1.95 mmol), and the reaction mixture was stirred for 5 h. After removal of CF3COOH, the residue was dissolved in DCM, washed with sat. ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]C1 | C1CCNC1 | c1ccccc1.C1C[NH]CC[NH]1.C1CCNC1.c1nnn[nH]1.c1ccccc1 | HO- | null | null | 5 | CC(C)(C)OC(=O)N1CC(n2nnc(-c3ccc(F)cc3F)n2)CC1C(=O)N1CCN(c2ccccc2C#N)CC1>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-911d1835086b4f06a416ec2bd8c09d3c | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccccc1>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccccc2)CC1 | [BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].FC1=C(C=CC(=C1)F)C=1N=NN(N1)C1CC(NC1)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1.C(C1=CC=CC=C1)=O.C(C)(=O)O>>C(C1=CC=CC=C1)N1[C@@H](C[C@@H](C1)N1N=C(N=N1)C1=C(C=C(C=C1)F)F)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH:15]2[CH2:16][CH:17]([n:18]3[n:19][n:20][c:21](-[c:22]4[cH:23][cH:24][c:25]([F:26])[cH:27][c:28]4[F:29])[n:30]3)[CH2:31][NH:32]2)[CH2:40][CH2:41]1.O=[CH:33][c:34]1[cH:35][cH:36][cH:37][cH:38][cH:39]1>>[N:1]#[C:2][c:3]1[cH:4][c... | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccccc1 | N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccccc2)CC1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | reductive amination | f320c54beea598cd731a01400cf9495fa26416685f3307ec69cb487e38cf79c3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C([C@@H]1C[C@H](n2nnc(-c3ccccc3)n2)CN1Cc1ccccc1)N1CCN(c2ccccc2)CC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1)-[C:14]>>[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[C@@H;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:14] | 2,069 | [{"value": 2069.0, "product": "C(C1=CC=CC=C1)N1[C@@H](C[C@@H](C1)N1N=C(N=N1)C1=C(C=C(C=C1)F)F)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | 2-(4-{4-[5-(2,4-Difluoro-phenyl)-tetrazol-2-yl]-pyrrolidine-2-carbonyl}-piperazin-1-yl)-benzonitrile (0.136 g, 0.29 mmol), benzaldehyde (0.034 g, 0.32 mmol) and acetic acid (cat) was dissolved in DCM (20 ml) and the solution was stirred for 20 min. Then NaBH(OAc)3 (0.12 g, 0.58 mmol) was carefully added. The resulting ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1C[NH]CC[NH]1.C1CC[NH]C1.c1nnn[nH]1.c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | null | 0.333333 | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccccc1>C(Cl)Cl>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccccc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-27cc4d9ed557464fae586541d235f246 | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccccc1F>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccccc2F)CC1 | FC1=C(C=CC(=C1)F)C=1N=NN(N1)C1CC(NC1)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1.FC1=C(C=O)C=CC=C1>>FC1=C(C=CC(=C1)F)C=1N=NN(N1)[C@H]1C[C@H](N(C1)CC1=C(C=CC=C1)F)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH:15]2[CH2:16][CH:17]([n:18]3[n:19][n:20][c:21](-[c:22]4[cH:23][cH:24][c:25]([F:26])[cH:27][c:28]4[F:29])[n:30]3)[CH2:31][NH:32]2)[CH2:41][CH2:42]1.O=[CH:33][c:34]1[cH:35][cH:36][cH:37][cH:38][c:39]1[F:40]>>[N:1]#[C:2][c:3]1[cH... | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccccc1F | N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccccc2F)CC1 | null | null | null | Heteroatom Alkylation and Arylation | reductive amination | f320c54beea598cd731a01400cf9495fa26416685f3307ec69cb487e38cf79c3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C([C@@H]1C[C@H](n2nnc(-c3ccccc3)n2)CN1Cc1ccccc1)N1CCN(c2ccccc2)CC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1)-[C:14]>>[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[C@@H;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:14] | 8.2 | [{"value": 8.2, "product": "FC1=C(C=CC(=C1)F)C=1N=NN(N1)[C@H]1C[C@H](N(C1)CC1=C(C=CC=C1)F)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 8.2, "product": "FC1=C(C=CC(=C1)F)C=1N=NN(N1)[C@H]1C[C@H](N(C1)CC1=C(C=CC=C1)F)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1", "details": "CALCULATEDPE... | null | null | null | null | As described for Example 1e, 2-(4-{4-[5-(2,4-difluoro-phenyl)-tetrazol-2-yl]-pyrrolidine-2-carbonyl}-piperazin-1-yl)-benzonitrile (60 mg, 0.13 mmol) was converted, using 2-fluoro-benzaldehyde (17 mg, 0.14 mmol) instead of benzaldehyde, to the title compound (6.1 mg, 8.2%) as light yellow oil. MS m/e=573.2 [M+H]+.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1C[NH]CC[NH]1.C1CC[NH]C1.c1nnn[nH]1.c1ccccc1.c1ccccc1 | Other | null | null | null | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccccc1F>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccccc2F)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-126a7447e25d4505b67f52ba87a30a8c | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1cccc(F)c1>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2cccc(F)c2)CC1 | FC1=C(C=CC(=C1)F)C=1N=NN(N1)C1CC(NC1)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1.FC=1C=C(C=O)C=CC1>>FC1=C(C=CC(=C1)F)C=1N=NN(N1)[C@H]1C[C@H](N(C1)CC1=CC(=CC=C1)F)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH:15]2[CH2:16][CH:17]([n:18]3[n:19][n:20][c:21](-[c:22]4[cH:23][cH:24][c:25]([F:26])[cH:27][c:28]4[F:29])[n:30]3)[CH2:31][NH:32]2)[CH2:41][CH2:42]1.O=[CH:33][c:34]1[cH:35][cH:36][cH:37][c:38]([F:39])[cH:40]1>>[N:1]#[C:2][c:3]1[... | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1cccc(F)c1 | N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2cccc(F)c2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | reductive amination | f320c54beea598cd731a01400cf9495fa26416685f3307ec69cb487e38cf79c3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C([C@@H]1C[C@H](n2nnc(-c3ccccc3)n2)CN1Cc1ccccc1)N1CCN(c2ccccc2)CC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1)-[C:14]>>[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[C@@H;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:14] | 13.3 | [{"value": 13.3, "product": "FC1=C(C=CC(=C1)F)C=1N=NN(N1)[C@H]1C[C@H](N(C1)CC1=CC(=CC=C1)F)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 13.3, "product": "FC1=C(C=CC(=C1)F)C=1N=NN(N1)[C@H]1C[C@H](N(C1)CC1=CC(=CC=C1)F)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1", "details": "CALCULATED... | null | null | null | null | As described for Example 1e, 2-(4-{4-[5-(2,4-difluoro-phenyl)-tetrazol-2-yl]-pyrrolidine-2-carbonyl}-piperazin-1-yl)-benzonitrile (60 mg, 0.13 mmol) was converted, using 3-fluoro-benzaldehyde (17 mg, 0.14 mmol) instead of benzaldehyde, to the title compound (9.9 mg, 13.3%) as light yellow oil. MS m/e=573.1 [M+H]+.
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1C[NH]CC[NH]1.C1CC[NH]C1.c1nnn[nH]1.c1ccccc1.c1ccccc1 | Other | null | null | null | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1cccc(F)c1>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2cccc(F)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-32697f2d5f9541cba4961872528a80ac | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccc(F)cc1>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccc(F)cc2)CC1 | FC1=C(C=CC(=C1)F)C=1N=NN(N1)C1CC(NC1)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1.FC1=CC=C(C=O)C=C1>>FC1=C(C=CC(=C1)F)C=1N=NN(N1)[C@H]1C[C@H](N(C1)CC1=CC=C(C=C1)F)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH:15]2[CH2:16][CH:17]([n:18]3[n:19][n:20][c:21](-[c:22]4[cH:23][cH:24][c:25]([F:26])[cH:27][c:28]4[F:29])[n:30]3)[CH2:31][NH:32]2)[CH2:41][CH2:42]1.O=[CH:33][c:34]1[cH:35][cH:36][c:37]([F:38])[cH:39][cH:40]1>>[N:1]#[C:2][c:3]1[... | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccc(F)cc1 | N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccc(F)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | reductive amination | f320c54beea598cd731a01400cf9495fa26416685f3307ec69cb487e38cf79c3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C([C@@H]1C[C@H](n2nnc(-c3ccccc3)n2)CN1Cc1ccccc1)N1CCN(c2ccccc2)CC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1)-[C:14]>>[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[C@@H;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:14] | 11 | [{"value": 11.0, "product": "FC1=C(C=CC(=C1)F)C=1N=NN(N1)[C@H]1C[C@H](N(C1)CC1=CC=C(C=C1)F)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.0, "product": "FC1=C(C=CC(=C1)F)C=1N=NN(N1)[C@H]1C[C@H](N(C1)CC1=CC=C(C=C1)F)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1", "details": "CALCULATED... | null | null | null | null | As described for Example 1e, 2-(4-{4-[5-(2,4-difluoro-phenyl)-tetrazol-2-yl]-pyrrolidine-2-carbonyl}-piperazin-1-yl)-benzonitrile (60 mg, 0.13 mmol) was converted, using 4-fluoro-benzaldehyde (17 mg, 0.14 mmol) instead of benzaldehyde, to the title compound (8.2 mg, 11%) as light yellow oil. MS m/e=573.1 [M+H]+.
Condit... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1C[NH]CC[NH]1.C1CC[NH]C1.c1nnn[nH]1.c1ccccc1.c1ccccc1 | Other | null | null | null | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccc(F)cc1>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccc(F)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-36fbc93493b840678e0c953b0d743c97 | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccccc1Cl>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccccc2Cl)CC1 | FC1=C(C=CC(=C1)F)C=1N=NN(N1)C1CC(NC1)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1.ClC1=C(C=O)C=CC=C1>>ClC1=C(CN2[C@@H](C[C@@H](C2)N2N=C(N=N2)C2=C(C=C(C=C2)F)F)C(=O)N2CCN(CC2)C2=C(C#N)C=CC=C2)C=CC=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH:15]2[CH2:16][CH:17]([n:18]3[n:19][n:20][c:21](-[c:22]4[cH:23][cH:24][c:25]([F:26])[cH:27][c:28]4[F:29])[n:30]3)[CH2:31][NH:32]2)[CH2:41][CH2:42]1.O=[CH:33][c:34]1[cH:35][cH:36][cH:37][cH:38][c:39]1[Cl:40]>>[N:1]#[C:2][c:3]1[c... | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccccc1Cl | N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccccc2Cl)CC1 | null | null | null | Heteroatom Alkylation and Arylation | reductive amination | f320c54beea598cd731a01400cf9495fa26416685f3307ec69cb487e38cf79c3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C([C@@H]1C[C@H](n2nnc(-c3ccccc3)n2)CN1Cc1ccccc1)N1CCN(c2ccccc2)CC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1)-[C:14]>>[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[C@@H;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:14] | 14.4 | [{"value": 14.4, "product": "ClC1=C(CN2[C@@H](C[C@@H](C2)N2N=C(N=N2)C2=C(C=C(C=C2)F)F)C(=O)N2CCN(CC2)C2=C(C#N)C=CC=C2)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.4, "product": "ClC1=C(CN2[C@@H](C[C@@H](C2)N2N=C(N=N2)C2=C(C=C(C=C2)F)F)C(=O)N2CCN(CC2)C2=C(C#N)C=CC=C2)C=CC=C1", "details": "CALC... | null | null | null | null | As described for Example 1e, 2-(4-{4-[5-(2,4-difluoro-phenyl)-tetrazol-2-yl]-pyrrolidine-2-carbonyl}-piperazin-1-yl)-benzonitrile (60 mg, 0.13 mmol) was converted, using 2-chloro-benzaldehyde (20 mg, 0.14 mmol) instead of benzaldehyde, to the title compound (11 mg, 14.4%) as light yellow oil. MS m/e=589.1 (75%); 591.1 ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1C[NH]CC[NH]1.C1CC[NH]C1.c1nnn[nH]1.c1ccccc1.c1ccccc1 | Other | null | null | null | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccccc1Cl>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccccc2Cl)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b83591f00bf54c4ebab73c1d69d66953 | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1cccc(Cl)c1>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2cccc(Cl)c2)CC1 | FC1=C(C=CC(=C1)F)C=1N=NN(N1)C1CC(NC1)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1.ClC=1C=C(C=O)C=CC1>>ClC=1C=C(CN2[C@@H](C[C@@H](C2)N2N=C(N=N2)C2=C(C=C(C=C2)F)F)C(=O)N2CCN(CC2)C2=C(C#N)C=CC=C2)C=CC1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH:15]2[CH2:16][CH:17]([n:18]3[n:19][n:20][c:21](-[c:22]4[cH:23][cH:24][c:25]([F:26])[cH:27][c:28]4[F:29])[n:30]3)[CH2:31][NH:32]2)[CH2:41][CH2:42]1.O=[CH:33][c:34]1[cH:35][cH:36][cH:37][c:38]([Cl:39])[cH:40]1>>[N:1]#[C:2][c:3]1... | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1cccc(Cl)c1 | N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2cccc(Cl)c2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | reductive amination | f320c54beea598cd731a01400cf9495fa26416685f3307ec69cb487e38cf79c3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C([C@@H]1C[C@H](n2nnc(-c3ccccc3)n2)CN1Cc1ccccc1)N1CCN(c2ccccc2)CC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1)-[C:14]>>[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[C@@H;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:14] | 10.1 | [{"value": 10.0, "product": "ClC=1C=C(CN2[C@@H](C[C@@H](C2)N2N=C(N=N2)C2=C(C=C(C=C2)F)F)C(=O)N2CCN(CC2)C2=C(C#N)C=CC=C2)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.1, "product": "ClC=1C=C(CN2[C@@H](C[C@@H](C2)N2N=C(N=N2)C2=C(C=C(C=C2)F)F)C(=O)N2CCN(CC2)C2=C(C#N)C=CC=C2)C=CC1", "details": "CALC... | null | null | null | null | As described for Example 1e, 2-(4-{4-[5-(2,4-difluoro-phenyl)-tetrazol-2-yl]-pyrrolidine-2-carbonyl}-piperazin-1-yl)-benzonitrile (60 mg, 0.13 mmol) was converted, using 3-chloro-benzaldehyde (20 mg, 0.14 mmol) instead of benzaldehyde, to the title compound (7.7 mg, 10%) as light yellow oil. MS m/e=589.1 (75%); 591.1 (... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1C[NH]CC[NH]1.C1CC[NH]C1.c1nnn[nH]1.c1ccccc1.c1ccccc1 | Other | null | null | null | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1cccc(Cl)c1>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2cccc(Cl)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-773fcfab1fe8415990e4a99c994cf1fb | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccc(Cl)cc1>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccc(Cl)cc2)CC1 | FC1=C(C=CC(=C1)F)C=1N=NN(N1)C1CC(NC1)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1.ClC1=CC=C(C=O)C=C1>>ClC1=CC=C(CN2[C@@H](C[C@@H](C2)N2N=C(N=N2)C2=C(C=C(C=C2)F)F)C(=O)N2CCN(CC2)C2=C(C#N)C=CC=C2)C=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH:15]2[CH2:16][CH:17]([n:18]3[n:19][n:20][c:21](-[c:22]4[cH:23][cH:24][c:25]([F:26])[cH:27][c:28]4[F:29])[n:30]3)[CH2:31][NH:32]2)[CH2:41][CH2:42]1.O=[CH:33][c:34]1[cH:35][cH:36][c:37]([Cl:38])[cH:39][cH:40]1>>[N:1]#[C:2][c:3]1... | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccc(Cl)cc1 | N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccc(Cl)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | reductive amination | f320c54beea598cd731a01400cf9495fa26416685f3307ec69cb487e38cf79c3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C([C@@H]1C[C@H](n2nnc(-c3ccccc3)n2)CN1Cc1ccccc1)N1CCN(c2ccccc2)CC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1)-[C:14]>>[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[C@@H;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:14] | 11 | [{"value": 11.0, "product": "ClC1=CC=C(CN2[C@@H](C[C@@H](C2)N2N=C(N=N2)C2=C(C=C(C=C2)F)F)C(=O)N2CCN(CC2)C2=C(C#N)C=CC=C2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.8, "product": "ClC1=CC=C(CN2[C@@H](C[C@@H](C2)N2N=C(N=N2)C2=C(C=C(C=C2)F)F)C(=O)N2CCN(CC2)C2=C(C#N)C=CC=C2)C=C1", "details": "CALC... | null | null | null | null | As described for Example 1e, 2-(4-{4-[5-(2,4-difluoro-phenyl)-tetrazol-2-yl]-pyrrolidine-2-carbonyl}-piperazin-1-yl)-benzonitrile (60 mg, 0.13 mmol) was converted, using 4-chloro-benzaldehyde (20 mg, 0.14 mmol) instead of benzaldehyde, to the title compound (8.3 mg, 11%) as light yellow oil. MS m/e=589.1 (75%); 591.1 (... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1C[NH]CC[NH]1.C1CC[NH]C1.c1nnn[nH]1.c1ccccc1.c1ccccc1 | Other | null | null | null | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccc(Cl)cc1>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccc(Cl)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5910c65e3a384586b898eba2120f05df | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=CC1CCCCC1>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2CC2CCCCC2)CC1 | FC1=C(C=CC(=C1)F)C=1N=NN(N1)C1CC(NC1)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1.C1(CCCCC1)C=O>>C1(CCCCC1)CN1[C@@H](C[C@@H](C1)N1N=C(N=N1)C1=C(C=C(C=C1)F)F)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1 | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH:15]2[CH2:16][CH:17]([n:18]3[n:19][n:20][c:21](-[c:22]4[cH:23][cH:24][c:25]([F:26])[cH:27][c:28]4[F:29])[n:30]3)[CH2:31][NH:32]2)[CH2:40][CH2:41]1.O=[CH:33][CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1>>[N:1]#[C:2][c:3]1[c... | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=CC1CCCCC1 | N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2CC2CCCCC2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | reductive amination | f320c54beea598cd731a01400cf9495fa26416685f3307ec69cb487e38cf79c3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C([C@@H]1C[C@H](n2nnc(-c3ccccc3)n2)CN1CC1CCCCC1)N1CCN(c2ccccc2)CC1 | O=[CH;D2;+0:1]-[C:2](-[C:3])-[C:4].[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1)-[C:14]>>[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[C@@H;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4])-[C:14] | 11.7 | [{"value": 11.7, "product": "C1(CCCCC1)CN1[C@@H](C[C@@H](C1)N1N=C(N=N1)C1=C(C=C(C=C1)F)F)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 11.7, "product": "C1(CCCCC1)CN1[C@@H](C[C@@H](C1)N1N=C(N=N1)C1=C(C=C(C=C1)F)F)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1", "details": "CALCULATEDPERC... | null | null | null | null | As described for Example 1e, 2-(4-{4-[5-(2,4-difluoro-phenyl)-tetrazol-2-yl]-pyrrolidine-2-carbonyl}-piperazin-1-yl)-benzonitrile (60 mg, 0.13 mmol) was converted, using cyclohexanecarbaldehyde (16 mg, 0.14 mmol) instead of benzaldehyde, to the title compound (8.5 mg, 11.7%) as light yellow oil. MS m/e=561.3 [M+H]+.
Co... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1C[NH]CC[NH]1.C1CC[NH]C1.c1nnn[nH]1.c1ccccc1.C1CCCCC1 | Other | null | null | null | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=CC1CCCCC1>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2CC2CCCCC2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f0e0e9801b341f6848f8acfa88b7a7c | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccc(F)c(F)c1>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccc(F)c(F)c2)CC1 | FC1=C(C=CC(=C1)F)C=1N=NN(N1)C1CC(NC1)C(=O)N1CCN(CC1)C1=C(C#N)C=CC=C1.FC=1C=C(C=O)C=CC1F>>FC=1C=C(CN2[C@@H](C[C@@H](C2)N2N=C(N=N2)C2=C(C=C(C=C2)F)F)C(=O)N2CCN(CC2)C2=C(C#N)C=CC=C2)C=CC1F | [N:1]#[C:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[N:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[CH:15]2[CH2:16][CH:17]([n:18]3[n:19][n:20][c:21](-[c:22]4[cH:23][cH:24][c:25]([F:26])[cH:27][c:28]4[F:29])[n:30]3)[CH2:31][NH:32]2)[CH2:42][CH2:43]1.O=[CH:33][c:34]1[cH:35][cH:36][c:37]([F:38])[c:39]([F:40])[cH:41]1>>[N:1]#[C:2]... | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccc(F)c(F)c1 | N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccc(F)c(F)c2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | reductive amination | f320c54beea598cd731a01400cf9495fa26416685f3307ec69cb487e38cf79c3 | 2d03f38884b1fbb0c0d6e6f2de31afb25102fec87f347c3a123e064c1bfef0ad | O=C([C@@H]1C[C@H](n2nnc(-c3ccccc3)n2)CN1Cc1ccccc1)N1CCN(c2ccccc2)CC1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[NH;D2;+0:13]-1)-[C:14]>>[C:5]-[#7:6](-[C:7](=[O;D1;H0:8])-[C@@H;D3;+0:9]1-[C:10]-[C:11]-[C:12]-[N;H0;D3;+0:13]-1-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:14] | 13.5 | [{"value": 13.5, "product": "FC=1C=C(CN2[C@@H](C[C@@H](C2)N2N=C(N=N2)C2=C(C=C(C=C2)F)F)C(=O)N2CCN(CC2)C2=C(C#N)C=CC=C2)C=CC1F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 13.5, "product": "FC=1C=C(CN2[C@@H](C[C@@H](C2)N2N=C(N=N2)C2=C(C=C(C=C2)F)F)C(=O)N2CCN(CC2)C2=C(C#N)C=CC=C2)C=CC1F", "details": "CALC... | null | null | null | null | As described for Example 1e, 2-(4-{4-[5-(2,4-difluoro-phenyl)-tetrazol-2-yl]-pyrrolidine-2-carbonyl}-piperazin-1-yl)-benzonitrile (60 mg, 0.13 mmol) was converted, using 3,4-difluoro-benzaldehyde (20 mg, 0.14 mmol) instead of benzaldehyde, to the title compound (10.4 mg, 13.5%) as light yellow oil. MS m/e=591.2 [M+H]+.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | c1ccccc1.C1C[NH]CC[NH]1.C1CC[NH]C1.c1nnn[nH]1.c1ccccc1.c1ccccc1 | Other | null | null | null | N#Cc1ccccc1N1CCN(C(=O)C2CC(n3nnc(-c4ccc(F)cc4F)n3)CN2)CC1.O=Cc1ccc(F)c(F)c1>>N#Cc1ccccc1N1CCN(C(=O)[C@@H]2C[C@H](n3nnc(-c4ccc(F)cc4F)n3)CN2Cc2ccc(F)c(F)c2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-910cea6623b74fb2b1ee706f15d664e0 | Clc1nc2ccccc2o1.O=C(OCc1ccccc1)N1CCNCC1>>O=C(OCc1ccccc1)N1CCN(c2nc3ccccc3o2)CC1 | ClC=1OC2=C(N1)C=CC=C2.N1(CCNCC1)C(=O)OCC1=CC=CC=C1.C(=O)([O-])[O-].[K+].[K+]>>C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1OC2=C(N1)C=CC=C2 | Cl[c:15]1[n:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]2[o:23]1.[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][NH:14][CH2:24][CH2:25]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][N:14]([c:15]2[n:16][c:17]3[cH:18][cH:19][cH:20][cH:21][c... | Clc1nc2ccccc2o1.O=C(OCc1ccccc1)N1CCNCC1 | O=C(OCc1ccccc1)N1CCN(c2nc3ccccc3o2)CC1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | dc7f56449be366095f55bb3453c30853f486d28651a4359a472bd78eeca0c4ec | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(OCc1ccccc1)N1CCN(c2nc3ccccc3o2)CC1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:1.[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#7:6]1-[C:7]-[C:8]-[N;H0;D3;+0:9](-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[c:4]:[#8;a:5]:2)-[C:10]-[C:11]-1 | 77.4 | [{"value": 77.0, "product": "C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1OC2=C(N1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.4, "product": "C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1OC2=C(N1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 8 | HOUR | A mixture of 2-chlorobenzoxazole (1.00 g, 6.51 mmol), benzyl 1-piperazinecarboxylate (1.43 g, 6.51 mmol), and K2CO3 (1.80 g, 13.0 mmol) in DMF (13 mL) was stirred at 100° C. overnight, cooled, diluted with water, and extracted with EtOAc. The extracts were combined, washed with water and brine, dried over Na2SO4 and co... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccc2ocnc2c1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.c1ccc2ocnc2c1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2ocnc2c1 | HCl | O.CN(C)C=O | 100 | 8 | Clc1nc2ccccc2o1.O=C(OCc1ccccc1)N1CCNCC1>O.CN(C)C=O>O=C(OCc1ccccc1)N1CCN(c2nc3ccccc3o2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-77e06490c243483cb610fca76a3fdc4f | ClI.O=C(OCc1ccccc1)N1CCN(c2nc3ccccc3o2)CC1>>O=C(OCc1ccccc1)N1CCN(c2nc3cc(I)ccc3o2)CC1 | C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1OC2=C(N1)C=CC=C2.ICl>>C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1OC2=C(N1)C=C(C=C2)I | Cl[I:20].[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][N:14]([c:15]2[n:16][c:17]3[cH:18][cH:19][cH:21][cH:22][c:23]3[o:24]2)[CH2:25][CH2:26]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][N:14]([c:15]2[n:16][c:17]3[cH:18][c:19]([I:20])[c... | ClI.O=C(OCc1ccccc1)N1CCN(c2nc3ccccc3o2)CC1 | O=C(OCc1ccccc1)N1CCN(c2nc3cc(I)ccc3o2)CC1 | null | null | C(C)(=O)O | Functional Group Interconversion | OtherReaction | c470576ff2f7b86aa529d1df087ace0fa7d38fd391894f28a43e2561d9d37acb | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | O=C(OCc1ccccc1)N1CCN(c2nc3ccccc3o2)CC1 | Cl-[I;H0;D1;+0:1].[#7;a:2]1:[c:3]:[#8;a:4]:[c:5]2:[c:6]:[c:7]:[cH;D2;+0:8]:[c:9]:[c:10]:1:2>>[I;H0;D1;+0:1]-[c;H0;D3;+0:8]1:[c:9]:[c:10]2:[#7;a:2]:[c:3]:[#8;a:4]:[c:5]:2:[c:6]:[c:7]:1 | null | [] | 60 | CELSIUS | 8 | HOUR | A mixture of 4-benzoxazol-2-yl-piperazine-1-carboxylic acid benzyl ester (0.50 g, 1.48 mmol) and iodine monochloride (0.265 g, 1.63 mmol) in acetic acid (4.94 mL) was stirred at 60° C. overnight, cooled, and concentrated in vacuo to provide the title compound, which was used without further purification, in Example 3.
... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2ocnc2c1 | HCl | C(C)(=O)O | 60 | 8 | ClI.O=C(OCc1ccccc1)N1CCN(c2nc3ccccc3o2)CC1>C(C)(=O)O>O=C(OCc1ccccc1)N1CCN(c2nc3cc(I)ccc3o2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8b005d31478d4b1bb3a11fdf7a2d4054 | O=C(OCc1ccccc1)N1CCN(c2nc3cc(I)ccc3o2)CC1.Sc1cccc2ccccc12>>O=C(OCc1ccccc1)N1CCN(c2nc3cc(Sc4cccc5ccccc45)ccc3o2)CC1 | C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1OC2=C(N1)C=C(C=C2)I.C1(=CC=CC2=CC=CC=C12)S.C(=O)([O-])[O-].[K+].[K+]>>C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1OC2=C(N1)C=C(C=C2)SC2=CC=CC1=CC=CC=C21 | I[c:19]1[cH:18][c:17]2[n:16][c:15]([N:14]3[CH2:13][CH2:12][N:11]([C:2](=[O:1])[O:3][CH2:4][c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[CH2:36][CH2:35]3)[o:34][c:33]2[cH:32][cH:31]1.[SH:20][c:21]1[cH:22][cH:23][cH:24][c:25]2[cH:26][cH:27][cH:28][cH:29][c:30]12>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[... | O=C(OCc1ccccc1)N1CCN(c2nc3cc(I)ccc3o2)CC1.Sc1cccc2ccccc12 | O=C(OCc1ccccc1)N1CCN(c2nc3cc(Sc4cccc5ccccc45)ccc3o2)CC1 | null | [Cu]I | C(C)(C)O.C(Cl)Cl.CO | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution thiol | 7b7ee2188f41b541909aa452da28b59c4faf279efd11a49585cd2d93c2b7c23f | 97e4acce9b485bd597e518526ab4e9623782b1c9043b6e30dd257d386e3e5b01 | O=C(OCc1ccccc1)N1CCN(c2nc3cc(Sc4cccc5ccccc45)ccc3o2)CC1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#8;a:6]:[c:7]:2:[c:8]:[c:9]:1.[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[S;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[c:3]2:[#7;a:4]:[c:5]:[#8;a:6]:[c:7]:2:[c:8]:[c:9]:1):[c:13] | 31 | [{"value": 31.0, "product": "C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1OC2=C(N1)C=C(C=C2)SC2=CC=CC1=CC=CC=C21", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A mixture of 4-(5-iodobenzoxazol-2-yl)piperazine-1-carboxylic acid benzyl ester, prepared in Example 2 (1.48 mmol theory), 1-napthalenethiol (0.237 g, 1.48 mmol), CuI (0.042 g, 0.22 mmol), and K2CO3 (0.409 g, 2.96 mmol) in isopropanol was heated at 90° C. overnight, diluted with 20% MeOH in CH2Cl2, and filtered through... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic thiol | Monosulfide | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2ocnc2c1.c1ccc2ccccc2c1 | HI | [Cu]I.C(C)(C)O.C(Cl)Cl.CO | 90 | null | O=C(OCc1ccccc1)N1CCN(c2nc3cc(I)ccc3o2)CC1.Sc1cccc2ccccc12>[Cu]I.C(C)(C)O.C(Cl)Cl.CO>O=C(OCc1ccccc1)N1CCN(c2nc3cc(Sc4cccc5ccccc45)ccc3o2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6943e365059b4013867cc8c1b34d2de9 | Nc1c(O)cccc1[N+](=O)[O-].S=C=S>>O=[N+]([O-])c1cccc2oc(=S)[nH]c12 | [OH-].[K+].C(=S)=S.NC1=C(C=CC=C1[N+](=O)[O-])O>>[N+](=O)([O-])C1=CC=CC2=C1NC(O2)=S | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([OH:9])[c:13]1[NH2:12].S=[C:10]=[S:11]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][c:8]2[o:9][c:10](=[S:11])[nH:12][c:13]12 | Nc1c(O)cccc1[N+](=O)[O-].S=C=S | O=[N+]([O-])c1cccc2oc(=S)[nH]c12 | null | null | O.CCO | Aromatic Heterocycle Formation | OtherReaction | f36afddd3d02447b24211cf69428ebe01673562ce3164199a8201b5c93803a28 | 94f29894f73fa405cebace4e3be9b5e7b09e8f95c1bb353d798627950215e50f | S=c1[nH]c2ccccc2o1 | S=[C;H0;D2;+0:1]=[S;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6](-[OH;D1;+0:7]):[c:8]>>[S;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:8]):[o;H0;D2;+0:7]:1 | 79 | [{"value": 79.0, "product": "[N+](=O)([O-])C1=CC=CC2=C1NC(O2)=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.6, "product": "[N+](=O)([O-])C1=CC=CC2=C1NC(O2)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of KOH (3.31 g, 59.0 mmol) in EtOH and water was treated with carbon disulfide (10.4 g, 136.3 mmol) followed by 2-amino-3-nitrophenol (7.00 g, 45.4 mmol). The mixture was heated at reflux temperature overnight, cooled, concentrated, acidified with 1M HCl and filtered. The filtercake was washed with water and... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine | Thiocarbonyl | c1ccccc1 | c1nc2ccccc2o1 | c1nc2ccccc2o1 | Other | O.CCO | null | null | Nc1c(O)cccc1[N+](=O)[O-].S=C=S>O.CCO>O=[N+]([O-])c1cccc2oc(=S)[nH]c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2db2ddd664ff4ee0a45b1eb1ec313f00 | O=C(OCc1ccccc1)N1CCNCC1.O=[N+]([O-])c1cccc2oc(=S)[nH]c12>>O=C(OCc1ccccc1)N1CCN(c2nc3c([N+](=O)[O-])cccc3o2)CC1 | [N+](=O)([O-])C1=CC=CC2=C1NC(O2)=S.N1(CCNCC1)C(=O)OCC1=CC=CC=C1>>C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1OC2=C(N1)C(=CC=C2)[N+](=O)[O-] | [O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][NH:14][CH2:27][CH2:28]1.S=[c:15]1[nH:16][c:17]2[c:18]([N+:19](=[O:20])[O-:21])[cH:22][cH:23][cH:24][c:25]2[o:26]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][N:14]([c:15]2[n:16][c:17]3[c:18... | O=C(OCc1ccccc1)N1CCNCC1.O=[N+]([O-])c1cccc2oc(=S)[nH]c12 | O=C(OCc1ccccc1)N1CCN(c2nc3c([N+](=O)[O-])cccc3o2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b037f1d021ad7ee678b4b96ce7aa3a257db8746996f43332b49588c1a48ab045 | 22c1f731d65e73470bc5e94b772e5886f196dfe5bc1b901343a6a3cfc4e67067 | O=C(OCc1ccccc1)N1CCN(c2nc3ccccc3o2)CC1 | S=[c;H0;D3;+0:1]1:[#8;a:2]:[c:3](:[c:4]):[c:5](:[c:6]):[nH;D2;+0:7]:1.[#7:8]1-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-1>>[c:6]:[c:5]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:1](-[N;H0;D3;+0:11]2-[C:10]-[C:9]-[#7:8]-[C:13]-[C:12]-2):[#8;a:2]:[c:3]:1:[c:4] | null | [] | null | null | null | null | A mixture of 4-nitro-3H-benzoxazole-2-thione (7.00 g, 35.7 mmol) and benzyl 1-piperazinecarboxylate (15.72 g, 71.36 mmol) in xylenes was heated at reflux temperature overnight, cooled and concentrated in vacuo to provide the title compound which was used, without further purification, in Example 8.
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Thiocarbonyl | Tertiary amine | C1C[NH]CCN1.c1nc2ccccc2o1 | C1C[NH]CC[NH]1.c1ccc2ocnc2c1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2ocnc2c1 | Other | null | null | null | O=C(OCc1ccccc1)N1CCNCC1.O=[N+]([O-])c1cccc2oc(=S)[nH]c12>>O=C(OCc1ccccc1)N1CCN(c2nc3c([N+](=O)[O-])cccc3o2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fba89f3bd59b43ef9b44ba6c7ff64902 | O=C(OCc1ccccc1)N1CCN(c2nc3c([N+](=O)[O-])cccc3o2)CC1>>Nc1cccc2oc(N3CCN(C(=O)OCc4ccccc4)CC3)nc12 | Cl[Sn]Cl.Cl.[OH-].[Na+].C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1OC2=C(N1)C(=CC=C2)[N+](=O)[O-]>>C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1OC2=C(N1)C(=CC=C2)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]2[o:7][c:8]([N:9]3[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][CH2:16][c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[CH2:23][CH2:24]3)[n:25][c:26]12>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[o:7][c:8]([N:9]3[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][CH2:16][c:17]4[cH:18][cH:19][c... | O=C(OCc1ccccc1)N1CCN(c2nc3c([N+](=O)[O-])cccc3o2)CC1 | Nc1cccc2oc(N3CCN(C(=O)OCc4ccccc4)CC3)nc12 | null | null | CO.C(Cl)Cl.CCO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(OCc1ccccc1)N1CCN(c2nc3ccccc3o2)CC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]1:[#7;a:5]:[c:6]:[#8;a:7]:[c:8]:1>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]1:[#7;a:5]:[c:6]:[#8;a:7]:[c:8]:1 | 24 | [{"value": 24.0, "product": "C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1OC2=C(N1)C(=CC=C2)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-(4-nitrobenzoxazol-2-yl)piperazine-1-carboxylic acid benzyl ester, from Example 7 (35.7 mmol theory), SnCl2 (40.25 g, 178.4 mmol), and concentrated HCl solution (4.46 mL) in EtOH was heated at 70° C. overnight, cooled, diluted with 20% MeOH in CH2Cl2, neutralized with NaOH to pH 8-10 and extracted with C... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2ocnc2c1.C1C[NH]CC[NH]1.c1ccccc1 | Other | CO.C(Cl)Cl.CCO | null | null | O=C(OCc1ccccc1)N1CCN(c2nc3c([N+](=O)[O-])cccc3o2)CC1>CO.C(Cl)Cl.CCO>Nc1cccc2oc(N3CCN(C(=O)OCc4ccccc4)CC3)nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f7800f338ea840ef9f35c02020278be5 | O=C(OCc1ccccc1)N1CCN(c2nc3c(I)cccc3o2)CC1.Sc1cccc2ccccc12>>O=C(OCc1ccccc1)N1CCN(c2nc3c(Sc4cccc5ccccc45)cccc3o2)CC1 | C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1OC2=C(N1)C(=CC=C2)I.C1=CC=C2C(=C1)C=CC=C2S.C(CO)O.C(=O)([O-])[O-].[K+].[K+]>>C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1OC2=C(N1)C(=CC=C2)SC2=CC=CC1=CC=CC=C21 | I[c:18]1[c:17]2[n:16][c:15]([N:14]3[CH2:13][CH2:12][N:11]([C:2](=[O:1])[O:3][CH2:4][c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[CH2:36][CH2:35]3)[o:34][c:33]2[cH:32][cH:31][cH:30]1.[SH:19][c:20]1[cH:21][cH:22][cH:23][c:24]2[cH:25][cH:26][cH:27][cH:28][c:29]12>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[... | O=C(OCc1ccccc1)N1CCN(c2nc3c(I)cccc3o2)CC1.Sc1cccc2ccccc12 | O=C(OCc1ccccc1)N1CCN(c2nc3c(Sc4cccc5ccccc45)cccc3o2)CC1 | null | [Cu]I | C(C)(C)O.C(Cl)Cl.CO | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution thiol | 7b7ee2188f41b541909aa452da28b59c4faf279efd11a49585cd2d93c2b7c23f | 97e4acce9b485bd597e518526ab4e9623782b1c9043b6e30dd257d386e3e5b01 | O=C(OCc1ccccc1)N1CCN(c2nc3c(Sc4cccc5ccccc45)cccc3o2)CC1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#8;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1.[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[S;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]2:[#8;a:6]:[c:7]:[#7;a:8]:[c:9]:2:1):[c:13] | 99.8 | [{"value": 93.0, "product": "C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1OC2=C(N1)C(=CC=C2)SC2=CC=CC1=CC=CC=C21", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.8, "product": "C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1OC2=C(N1)C(=CC=C2)SC2=CC=CC1=CC=CC=C21", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A mixture of 4-(4-iodobenzoxazol-2-yl)piperazine-1-carboxylic acid benzyl ester (0.80 g, 1.73 mmol), 1-naphthylthiol (0.276 g, 1.73 mmol), CuI (0.066 g, 0.35 mmol), ethylene glycol (0.214 g, 3.45 mmol), and K2CO3(0.477 g, 3.45 mmol) in isopropanol was heated at 90° C. overnight, cooled, diluted with 20% MeOH in CH2Cl2 ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic thiol | Monosulfide | c1ccc2ocnc2c1 | c1ccc2ocnc2c1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2ccccc2c1.c1ccc2ocnc2c1 | HI | [Cu]I.C(C)(C)O.C(Cl)Cl.CO | 90 | null | O=C(OCc1ccccc1)N1CCN(c2nc3c(I)cccc3o2)CC1.Sc1cccc2ccccc12>[Cu]I.C(C)(C)O.C(Cl)Cl.CO>O=C(OCc1ccccc1)N1CCN(c2nc3c(Sc4cccc5ccccc45)cccc3o2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e9b5aa7a5a744a7a83887a36cbc9113 | CC=O.ClCCCl.O=S(=O)(c1cccc2ccccc12)c1cccc2oc(N3CCNCC3)nc12>>CCN1CCN(c2nc3c(S(=O)(=O)c4cccc5ccccc45)cccc3o2)CC1.Cl.Cl | C1(=CC=CC2=CC=CC=C12)S(=O)(=O)C1=CC=CC2=C1N=C(O2)N2CCNCC2.C(C)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].C(C)(=O)O.ClCCCl>>Cl.Cl.C(C)N1CCN(CC1)C=1OC2=C(N1)C(=CC=C2)S(=O)(=O)C2=CC=CC1=CC=CC=C21 | O=[CH:2][CH3:1].C(C[Cl:32])[Cl:31].[NH:3]1[CH2:4][CH2:5][N:6]([c:7]2[n:8][c:9]3[c:10]([S:11](=[O:12])(=[O:13])[c:14]4[cH:15][cH:16][cH:17][c:18]5[cH:19][cH:20][cH:21][cH:22][c:23]45)[cH:24][cH:25][cH:26][c:27]3[o:28]2)[CH2:29][CH2:30]1>>[CH3:1][CH2:2][N:3]1[CH2:4][CH2:5][N:6]([c:7]2[n:8][c:9]3[c:10]([S:11](=[O:12])(=[O... | CC=O.ClCCCl.O=S(=O)(c1cccc2ccccc12)c1cccc2oc(N3CCNCC3)nc12 | CCN1CCN(c2nc3c(S(=O)(=O)c4cccc5ccccc45)cccc3o2)CC1.Cl.Cl | null | null | C(Cl)Cl.CO | Heteroatom Alkylation and Arylation | OtherReaction | 085eaff1b0b048ee147c1393dcef18f5c11441e172bca7b71cabccf71f8f6473 | 8302fdd87fbe9855a008f3b161f42a6084ba03b70a91cd831fb7f3a2246ad12a | O=S(=O)(c1cccc2ccccc12)c1cccc2oc(N3CCNCC3)nc12 | O=[CH;D2;+0:1]-[C;D1;H3:2].[#7:3]1-[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]-1.[Cl;H0;D1;+0:9]-C-C-[Cl;H0;D1;+0:10]>>[C;D1;H3:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:6]1-[C:5]-[C:4]-[#7:3]-[C:8]-[C:7]-1.[ClH;D0;+0:9].[ClH;D0;+0:10] | null | [] | null | null | 8 | HOUR | A mixture of 4-(1-naphthylsulfonyl)-2-piperazin-1-ylbenzoxazole (0.070 g, 0.18 mmol), acetaldehyde (0.016 g, 0.36 mmol), NaBH(OAc)3 (0.075 g, 0.36 mmol), and acetic acid (0.021 g, 0.36 mmol) in 1,2-dichloroethane was stirred at room temperature overnight, diluted with 20% MeOH in CH2Cl2 (with 0.5% NH4OH) and filtered t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary halide.Aldehyde.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccc2ccccc2c1.c1ccc2ocnc2c1 | HO- | C(Cl)Cl.CO | null | 8 | CC=O.ClCCCl.O=S(=O)(c1cccc2ccccc12)c1cccc2oc(N3CCNCC3)nc12>C(Cl)Cl.CO>CCN1CCN(c2nc3c(S(=O)(=O)c4cccc5ccccc45)cccc3o2)CC1.Cl.Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0f847610fae548e0b7fcaeb93863258e | O=[N+]([O-])c1cccc([N+](=O)[O-])c1O>>Nc1cccc(N)c1O | [N+](=O)([O-])C1=C(C(=CC=C1)[N+](=O)[O-])O>>NC1=C(C(=CC=C1)N)O | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([N+:7](=O)[O-])[c:8]1[OH:9]>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[c:8]1[OH:9] | O=[N+]([O-])c1cccc([N+](=O)[O-])c1O | Nc1cccc(N)c1O | null | [Pd] | CO | Reduction | OtherReaction | 6748a51a25102225412593c5a930e43f5a8904a80803177de025a6f83c59d65e | a303b0dfb15cc6bade463acf71681cf3ba7580b599dfa4d28d8caac83d08cd17 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5](-[N+;H0;D3:6](=O)-[O-]):[c:7]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]:[c:5](-[NH2;D1;+0:6]):[c:7] | 89 | [{"value": 89.0, "product": "NC1=C(C(=CC=C1)N)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.8, "product": "NC1=C(C(=CC=C1)N)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 2,6-dinitrophenol (2.50 g, 13.6 mmol) and 10% Pd/C (300 mg) in MeOH was shaken under H2 (40 psi) overnight and filtered. The filtrate was concentrated in vacuo to provide the title compound (1.50 g, 89%), characterized by NMR and mass spectral analyses.
Conditions: See reaction.notes.procedure_details.
Wor... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Nitro group | Primary amine.Primary amine | null | null | c1ccccc1 | Other | [Pd].CO | null | 8 | O=[N+]([O-])c1cccc([N+](=O)[O-])c1O>[Pd].CO>Nc1cccc(N)c1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-33955f38fde54746bd39becf7c2eed71 | Nc1cccc(N)c1O.S=C=S>>Nc1cccc2[nH]c(=S)oc12 | [OH-].[K+].C(=S)=S.NC1=C(C(=CC=C1)N)O>>NC1=CC=CC=2NC(OC21)=S | [NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH2:7])[c:11]1[OH:10].S=[C:8]=[S:9]>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[nH:7][c:8](=[S:9])[o:10][c:11]12 | Nc1cccc(N)c1O.S=C=S | Nc1cccc2[nH]c(=S)oc12 | null | null | O.CCO | Aromatic Heterocycle Formation | OtherReaction | f36afddd3d02447b24211cf69428ebe01673562ce3164199a8201b5c93803a28 | 94f29894f73fa405cebace4e3be9b5e7b09e8f95c1bb353d798627950215e50f | S=c1[nH]c2ccccc2o1 | S=[C;H0;D2;+0:1]=[S;D1;H0:2].[NH2;D1;+0:3]-[c:4](:[c:5]):[c:6](-[OH;D1;+0:7]):[c:8]>>[S;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:3]:[c:4](:[c:5]):[c:6](:[c:8]):[o;H0;D2;+0:7]:1 | 49.7 | [{"value": 45.0, "product": "NC1=CC=CC=2NC(OC21)=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.7, "product": "NC1=CC=CC=2NC(OC21)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of KOH (0.875 g, 15.6 mmol) in EtOH (14.3 mL) and water (2.6 mL) was treated with carbon disulfide (0.828 g, 10.9 mmol), followed by of 2,6-diaminophenol (1.50 g, 12.1 mmol). The mixture was heated at reflux temperature for 3 h, concentrated, neutralized with 1M HCl to pH 7, and extracted with EtOAc. The ext... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Primary amine | Thiocarbonyl | c1ccccc1 | c1nc2ccccc2o1 | c1nc2ccccc2o1 | Other | O.CCO | null | null | Nc1cccc(N)c1O.S=C=S>O.CCO>Nc1cccc2[nH]c(=S)oc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8d6b5b60b3cc4cb5a6a7f8bd0cf7055f | Nc1nc2ccc([N+](=O)[O-])cc2s1.[Cl-]>>O=[N+]([O-])c1ccc2nc(Cl)sc2c1 | N(=O)[O-].[Na+].NC=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-].[Na+].[Cl-]>>ClC=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-] | N[c:9]1[n:8][c:7]2[cH:6][cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:13][c:12]2[s:11]1.[Cl-:10]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][c:7]2[n:8][c:9]([Cl:10])[s:11][c:12]2[cH:13]1 | Nc1nc2ccc([N+](=O)[O-])cc2s1.[Cl-] | O=[N+]([O-])c1ccc2nc(Cl)sc2c1 | null | [O-]S(=O)(=O)[O-].[Cu+2] | OP(=O)(O)O.O | Functional Group Interconversion | OtherReaction | 4599048fb38f2d1af3922b92b925792c5f84e5e473c43843cae855107d585db2 | 9c224743a26d9e1c3135e4817dd611aec414d8ea156f02200a3aef865be78b01 | c1ccc2scnc2c1 | N-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[Cl-;H0;D0:6]>>[Cl;H0;D1;+0:6]-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1 | 95.3 | [{"value": 95.0, "product": "ClC=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.3, "product": "ClC=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A solution of NaNO2 (3.18 g, 46.1 mmol) in water was slowly added to a solution of 2-amino-6-nitro-benzothiazole (3.00 g, 15.4 mmol) in 85% H3PO4 over a period of 30 min at 0° C. The reaction solution was stirred for 1 hour and was gradually added to a solution of CuSO4 (7.61 g, 76.8 mmol) and NaCl (13.5 g, 230 mmol) i... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccc2scnc2c1 | Other | [O-]S(=O)(=O)[O-].[Cu+2].OP(=O)(O)O.O | null | 1 | Nc1nc2ccc([N+](=O)[O-])cc2s1.[Cl-]>[O-]S(=O)(=O)[O-].[Cu+2].OP(=O)(O)O.O>O=[N+]([O-])c1ccc2nc(Cl)sc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9ce445fe55a1405e8ec597df0c6fc1cc | O=C(OCc1ccccc1)N1CCNCC1.O=[N+]([O-])c1ccc2nc(Cl)sc2c1>>O=C(OCc1ccccc1)N1CCN(c2nc3ccc([N+](=O)[O-])cc3s2)CC1 | ClC=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-].N1(CCNCC1)C(=O)OCC1=CC=CC=C1.C(=O)(O)[O-].[Na+]>>C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-] | [O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][NH:14][CH2:27][CH2:28]1.Cl[c:15]1[n:16][c:17]2[cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24][c:25]2[s:26]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][N:14]([c:15]2[n:16][c:17]3[cH:18... | O=C(OCc1ccccc1)N1CCNCC1.O=[N+]([O-])c1ccc2nc(Cl)sc2c1 | O=C(OCc1ccccc1)N1CCN(c2nc3ccc([N+](=O)[O-])cc3s2)CC1 | null | null | CCO | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 3a958cd0a04b95e65d32e72c40c724b055048c6317e6bb3c9d11b89f3ac5d08d | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | O=C(OCc1ccccc1)N1CCN(c2nc3ccccc3s2)CC1 | Cl-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[#16;a:2]1:[c:3]:[c:4]:[#7;a:5]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1 | 61 | [{"value": 61.0, "product": "C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.9, "product": "C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-chloro-6-nitrobenzothiazole (1.00 g, 4.66 mmol), benzyl 1-piperazinecarboxylate (1.03 g, 4.66 mmol), and NaHCO3 (0.783 g, 9.32 mmol) in EtOH was heated at reflux temperature for 2 h, concentrated, and extracted with EtOAc. The combined extracts were dried over Na2SO4 and concentrated in vacuo to provide ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1ccc2scnc2c1 | C1C[NH]CC[NH]1.c1ccc2scnc2c1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2scnc2c1 | HCl | CCO | null | null | O=C(OCc1ccccc1)N1CCNCC1.O=[N+]([O-])c1ccc2nc(Cl)sc2c1>CCO>O=C(OCc1ccccc1)N1CCN(c2nc3ccc([N+](=O)[O-])cc3s2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2785adce26aa4f3cb36dcb4fb2aa1cc0 | O=C(OCc1ccccc1)N1CCN(c2nc3ccc([N+](=O)[O-])cc3s2)CC1>>Nc1ccc2nc(N3CCN(C(=O)OCc4ccccc4)CC3)sc2c1 | [OH-].[Na+].C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1SC2=C(N1)C=CC(=C2)[N+](=O)[O-].Cl[Sn]Cl.Cl>>C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1SC2=C(N1)C=CC(=C2)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][CH2:15][c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21]4)[CH2:22][CH2:23]3)[s:24][c:25]2[cH:26]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]2[n:6][c:7]([N:8]3[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][CH2:15][c:16]4[cH:17][cH:18][cH:19][c... | O=C(OCc1ccccc1)N1CCN(c2nc3ccc([N+](=O)[O-])cc3s2)CC1 | Nc1ccc2nc(N3CCN(C(=O)OCc4ccccc4)CC3)sc2c1 | null | null | O.CCO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(OCc1ccccc1)N1CCN(c2nc3ccccc3s2)CC1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | 77 | [{"value": 77.0, "product": "C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1SC2=C(N1)C=CC(=C2)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.5, "product": "C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1SC2=C(N1)C=CC(=C2)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | A mixture of 4-(6-nitrobenzothiazol-2-yl)piperazine-1-carboxylic acid benzyl ester (1.13 g, 2.84 mmol), SnCl2 (2.56 g, 11.3 mmol), and conc. HCl (0.35 mL, 4.25 mmol) in EtOH was heated at 70° C. overnight, diluted with water, neutralized with 1 N NaOH to pH 10, and extracted with CH2Cl2. The combined extracts were filt... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2scnc2c1.C1C[NH]CC[NH]1.c1ccccc1 | Other | O.CCO | 70 | null | O=C(OCc1ccccc1)N1CCN(c2nc3ccc([N+](=O)[O-])cc3s2)CC1>O.CCO>Nc1ccc2nc(N3CCN(C(=O)OCc4ccccc4)CC3)sc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0e0b81e8b38c4a44917d8ddedd10f6bd | O=C(OCc1ccccc1)N1CCN(c2nc3ccc(I)cc3s2)CC1.Sc1cccc2ccccc12>>O=C(OCc1ccccc1)N1CCN(c2nc3ccc(Sc4cccc5ccccc45)cc3s2)CC1 | C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1SC2=C(N1)C=CC(=C2)I.C1(=CC=CC2=CC=CC=C12)S.C(=O)([O-])[O-].[K+].[K+]>>C(C1=CC=CC=C1)OC(=O)N1CCN(CC1)C=1SC2=C(N1)C=CC(=C2)SC2=CC=CC1=CC=CC=C21 | I[c:20]1[cH:19][cH:18][c:17]2[n:16][c:15]([N:14]3[CH2:13][CH2:12][N:11]([C:2](=[O:1])[O:3][CH2:4][c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[CH2:36][CH2:35]3)[s:34][c:33]2[cH:32]1.[SH:21][c:22]1[cH:23][cH:24][cH:25][c:26]2[cH:27][cH:28][cH:29][cH:30][c:31]12>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[... | O=C(OCc1ccccc1)N1CCN(c2nc3ccc(I)cc3s2)CC1.Sc1cccc2ccccc12 | O=C(OCc1ccccc1)N1CCN(c2nc3ccc(Sc4cccc5ccccc45)cc3s2)CC1 | null | [Cu]I | CO.C(Cl)Cl.C(C)(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution thiol | 4bddd5977ed58160a1ff39c2f161ed63d64af968ab6551e76293ce677afafa68 | 97e4acce9b485bd597e518526ab4e9623782b1c9043b6e30dd257d386e3e5b01 | O=C(OCc1ccccc1)N1CCN(c2nc3ccc(Sc4cccc5ccccc45)cc3s2)CC1 | I-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1.[SH;D1;+0:10]-[c:11](:[c:12]):[c:13]>>[c:12]:[c:11](-[S;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[#7;a:5]:[c:6]:[#16;a:7]:[c:8]:2:[c:9]:1):[c:13] | null | [] | 90 | CELSIUS | null | null | A mixture of 4-(6-iodobenzothiazol-2-yl)piperazine-1-carboxylic acid benzyl ester (0.370 g, 0.77 mmol), 1-napthalenethiol (0.124 g, 0.77 mmol), CuI (0.015 g, 0.08 mmol), and K2CO3 (0.213 g, 0.77 mmol) in isopropanol was heated at 90° C. overnight, cooled to 25° C., diluted with 20% MeOH in CH2Cl2, and filtered through ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic thiol | Monosulfide | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccc2scnc2c1.c1ccc2ccccc2c1 | HI | [Cu]I.CO.C(Cl)Cl.C(C)(C)O | 90 | null | O=C(OCc1ccccc1)N1CCN(c2nc3ccc(I)cc3s2)CC1.Sc1cccc2ccccc12>[Cu]I.CO.C(Cl)Cl.C(C)(C)O>O=C(OCc1ccccc1)N1CCN(c2nc3ccc(Sc4cccc5ccccc45)cc3s2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dccd644595f345ec96dcc6a036f4cd13 | CC(=O)c1c(C)cccc1N.N#CCCl>>Cc1cccc2nc(CCl)nc(C)c12 | NC1=C(C(=CC=C1)C)C(C)=O.ClCC#N>>ClCC1=NC2=CC=CC(=C2C(=N1)C)C | O=[C:12]([CH3:13])[c:14]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]1[NH2:7].[C:8]([CH2:9][Cl:10])#[N:11]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[n:7][c:8]([CH2:9][Cl:10])[n:11][c:12]([CH3:13])[c:14]12 | CC(=O)c1c(C)cccc1N.N#CCCl | Cc1cccc2nc(CCl)nc(C)c12 | null | null | Cl.O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | 3cb539af45b29ab138fb7995eaf0f036952c2aaf5ed7aaeb63dbf2aa902a2f24 | d84c40f0e5b9678b8aec89aba887b0bfbad68faf41e24fc5e70a5868fcbd93bc | c1ccc2ncncc2c1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5](-[NH2;D1;+0:6]):[c:7].[Cl;D1;H0:8]-[C:9]-[C;H0;D2;+0:10]#[N;H0;D1;+0:11]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:11]:[c;H0;D3;+0:10](-[C:9]-[Cl;D1;H0:8]):[n;H0;D2;+0:6]:[c:5](:[c:7]):[c:3]:1:[c:4] | null | [] | null | null | null | null | Prepared by reacting 1-(2-amino-6-methyl-phenyl)-ethanone with chloroacetonitrile in dioxane while piping in hydrogen chloride at 30-38° C.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitrile.Primary amine | null | c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | HO- | Cl.O1CCOCC1 | null | null | CC(=O)c1c(C)cccc1N.N#CCCl>Cl.O1CCOCC1>Cc1cccc2nc(CCl)nc(C)c12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6f2754fdc83c48d2944769c8515ade70 | CC#CCn1c(N2CCC[C@@H](NC(=O)OC(C)(C)C)C2)nc2c1c(=O)[nH]c(=O)n2C.OCc1ccoc1>>CC#CCn1c(N2CCC[C@@H](NC(=O)OC(C)(C)C)C2)nc2c1c(=O)n(Cc1ccoc1)c(=O)n2C | CN1C(NC(C=2N(C(=NC12)N1C[C@@H](CCC1)NC(=O)OC(C)(C)C)CC#CC)=O)=O.O1C=C(C=C1)CO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.N(=NC(=O)OC(C)C)C(=O)OC(C)C.C([O-])([O-])=O.[K+].[K+]>>O1C=C(C=C1)CN1C(=O)N(C=2N=C(N(C2C1=O)CC#CC)N1C[C@@H](CCC1)NC(=O)OC(C)(C)C)C | [CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH2:9][CH2:10][C@@H:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20]2)[n:21][c:22]2[c:23]1[c:24](=[O:25])[nH:26][c:33](=[O:34])[n:35]2[CH3:36].O[CH2:27][c:28]1[cH:29][cH:30][o:31][cH:32]1>>[CH3:1][C:2]#[C:3][CH2:4][n:5]1[c:6]([N:7]2[CH2:8][CH... | CC#CCn1c(N2CCC[C@@H](NC(=O)OC(C)(C)C)C2)nc2c1c(=O)[nH]c(=O)n2C.OCc1ccoc1 | CC#CCn1c(N2CCC[C@@H](NC(=O)OC(C)(C)C)C2)nc2c1c(=O)n(Cc1ccoc1)c(=O)n2C | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 2cab79c43377c283abf3487b21b498a292c6ee2b50151eedaf25e95e3c08de3b | 2ab4024aa17b6e89368e6fe8ee731d32c7611cb9b23de403e301e8362fea90b1 | O=c1[nH]c2nc(N3CCCCC3)[nH]c2c(=O)n1Cc1ccoc1 | O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#8;a:5]:[c:6]:1.[C:7]#[C:8]-[C:9]-[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]2:[#7;a:14](-[C;D1;H3:15]):[c:16](=[O;D1;H0:17]):[nH;D2;+0:18]:[c:19](=[O;D1;H0:20]):[c:21]:1:2>>[C:7]#[C:8]-[C:9]-[#7;a:10]1:[c:11]:[#7;a:12]:[c:13]2:[#7;a:14](-[C;D1;H3:15]):[c:16](=[O;D1;H0:17]):[n;H0;D3;+0:18](-[... | null | [] | null | null | 8 | HOUR | A mixture of 300 mg of 3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-(tert.-butyloxycarbonyl-amino)-piperidin-1-yl]-xanthine, 95 μl furan-3-yl-methanol, 302 mg triphenylphosphine and 226 μl diisopropyl azodicarboxylate in 4 ml tetrahydrofuran is stirred overnight at ambient temperature. For working up the reaction mixture is comb... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | C1CC[NH]CC1.c1ncc2[nH]cnc2n1.c1ccoc1 | HO- | O1CCCC1 | null | 8 | CC#CCn1c(N2CCC[C@@H](NC(=O)OC(C)(C)C)C2)nc2c1c(=O)[nH]c(=O)n2C.OCc1ccoc1>O1CCCC1>CC#CCn1c(N2CCC[C@@H](NC(=O)OC(C)(C)C)C2)nc2c1c(=O)n(Cc1ccoc1)c(=O)n2C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7438233d572e4ad3b5ef167c77f06fa9 | CC#CCn1c(N2CCC[C@@H](NC(=O)OC(C)(C)C)C2)nc2c1c(=O)n(Cc1ccc(C=O)o1)c(=O)n2C.NOS(=O)(=O)O>>CC#CCn1c(N2CCC[C@@H](NC(=O)OC(C)(C)C)C2)nc2c1c(=O)n(Cc1ccc(C#N)o1)c(=O)n2C | C(=O)C1=CC=C(O1)CN1C(=O)N(C=2N=C(N(C2C1=O)CC#CC)N1C[C@@H](CCC1)NC(=O)OC(C)(C)C)C.NOS(=O)(=O)O.N1=CC=CC=C1>>C(#N)C1=CC=C(O1)CN1C(=O)N(C=2N=C(N(C2C1=O)CC#CC)N1C[C@@H](CCC1)NC(=O)OC(C)(C)C)C | O=[CH:32][c:31]1[cH:30][cH:29][c:28]([CH2:27][n:26]2[c:24](=[O:25])[c:23]3[n:5]([CH2:4][C:3]#[C:2][CH3:1])[c:6]([N:7]4[CH2:8][CH2:9][CH2:10][C@@H:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20]4)[n:21][c:22]3[n:37]([CH3:38])[c:35]2=[O:36])[o:34]1.O=S(=O)(O)O[NH2:33]>>[CH3:1][C:2]#[C:3][CH2:4... | CC#CCn1c(N2CCC[C@@H](NC(=O)OC(C)(C)C)C2)nc2c1c(=O)n(Cc1ccc(C=O)o1)c(=O)n2C.NOS(=O)(=O)O | CC#CCn1c(N2CCC[C@@H](NC(=O)OC(C)(C)C)C2)nc2c1c(=O)n(Cc1ccc(C#N)o1)c(=O)n2C | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 748a00525e7f639e600a6b1229bb8ce947b6e2e96d815c0b05b54470e6cdbc2a | a27285857ea2428fb666a281ae1a2b961eec077cb33a106e48534c99bfe3d865 | O=c1[nH]c2nc(N3CCCCC3)[nH]c2c(=O)n1Cc1ccco1 | O-S(=O)(=O)-O-[NH2;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[#8;a:5]:[c:6]>>[N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[#8;a:5]:[c:6] | null | [] | null | null | null | null | Prepared by reacting 1-[(5-formyl-furan-2-yl)methyl]-3-methyl-7-(2-butyn-1-yl)-8-[(R)-3-(tert.-butyloxycarbonylamino)-piperidin-1-yl]-xanthine with hydroxylamine-O-sulfonic acid and pyridine in toluene at reflux temperature.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared; at reflux temperature | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Nitrile | null | null | C1CC[NH]CC1.c1ncc2[nH]cnc2n1.c1ccoc1 | HO- | C1(=CC=CC=C1)C | null | null | CC#CCn1c(N2CCC[C@@H](NC(=O)OC(C)(C)C)C2)nc2c1c(=O)n(Cc1ccc(C=O)o1)c(=O)n2C.NOS(=O)(=O)O>C1(=CC=CC=C1)C>CC#CCn1c(N2CCC[C@@H](NC(=O)OC(C)(C)C)C2)nc2c1c(=O)n(Cc1ccc(C#N)o1)c(=O)n2C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e7688ff2973049e0bc24eed85ceeaad1 | CS(=O)(=O)Cl.O=Cc1ccc(CO)o1>>CS(=O)(=O)OCc1ccc(C=O)o1 | OCC1=CC=C(O1)C=O.CS(=O)(=O)Cl.C(C)N(CC)CC>>CS(=O)(=O)OCC1=CC=C(O1)C=O | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH:11]=[O:12])[o:13]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH:11]=[O:12])[o:13]1 | CS(=O)(=O)Cl.O=Cc1ccc(CO)o1 | CS(=O)(=O)OCc1ccc(C=O)o1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1ccoc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[#8;a:5]:[c:6]-[C:7]-[OH;D1;+0:8]>>[#8;a:5]:[c:6]-[C:7]-[O;H0;D2;+0:8]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | null | [] | null | null | null | null | Prepared by reacting 5-(hydroxymethyl)-2-furan-carboxaldehyde with methanesulfonic acid chloride in the presence of triethylamine in methylene chloride at ambient temperature. The crude product is further reacted without any more purification.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared; at ambie... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccoc1 | HCl | C(Cl)Cl | null | null | CS(=O)(=O)Cl.O=Cc1ccc(CO)o1>C(Cl)Cl>CS(=O)(=O)OCc1ccc(C=O)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-022d094184d2487280dbc9e4b0adf5ed | Cc1ccc2cccnc2c1Br>>Cc1ccc2cccnc2c1C#N | BrC=1C(=CC=C2C=CC=NC12)C.CN1C(CCC1)=O>>C(#N)C=1C(=CC=C2C=CC=NC12)C | Br[c:11]1[c:2]([CH3:1])[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][n:9][c:10]21>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][n:9][c:10]2[c:11]1[C:12]#[N:13] | Cc1ccc2cccnc2c1Br | Cc1ccc2cccnc2c1C#N | 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.[C-]#N.[Zn+2].[C-]#N | null | Miscellaneous | OtherReaction | afdbed702149bd75a12599fb8fb32cd13ecae3aee31c7d0c760a993e588426c5 | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccc2ncccc2c1 | Br-[c;H0;D3;+0:1](:[c:2](:[c:3]):[#7;a:4]:[c:5]):[c:6](-[C;D1;H3:7]):[c:8]>>[C;D1;H3:7]-[c:6](:[c:8]):[c;H0;D3;+0:1](-[C:9]#[N;D1;H0:10]):[c:2](:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | Prepared by reacting 8-bromo-7-methyl-quinoline with zinc cyanide in the presence of tetrakis(triphenylphosphine)palladium in N-methylpyrrolidinone under a protective gas atmosphere at 100-105° C.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared; at 100-105° C. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | Br- | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.[C-]#N.[Zn+2].[C-]#N | null | null | Cc1ccc2cccnc2c1Br>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.[C-]#N.[Zn+2].[C-]#N>Cc1ccc2cccnc2c1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e0260fce4ab4fcd8bec6f9e1e1222db | Cc1ccc2cccc(Br)c2n1>>Cc1ccc2cccc(C#N)c2n1 | CC1=NC2=C(C=CC=C2C=C1)Br.[Cu]C#N>>CC1=NC2=C(C=CC=C2C=C1)C#N | Br[c:9]1[cH:8][cH:7][cH:6][c:5]2[cH:4][cH:3][c:2]([CH3:1])[n:13][c:12]21>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][cH:8][c:9]([C:10]#[N:11])[c:12]2[n:13]1 | Cc1ccc2cccc(Br)c2n1 | Cc1ccc2cccc(C#N)c2n1 | null | null | CN1C(CCC1)=O | Miscellaneous | OtherReaction | afdbed702149bd75a12599fb8fb32cd13ecae3aee31c7d0c760a993e588426c5 | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccc2ncccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7]>>[N;D1;H0:8]#[C:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | null | null | Prepared by reacting 2-methyl-8-bromo-quinoline with copper(I)cyanide in N-methylpyrrolidinone under a protective gas atmosphere at 180° C.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared; at 180° C. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | Br- | CN1C(CCC1)=O | null | null | Cc1ccc2cccc(Br)c2n1>CN1C(CCC1)=O>Cc1ccc2cccc(C#N)c2n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b1ab0efff526456f88e8e045e28b22b0 | CCOC=C(C#N)C(=O)OCC.CSC(=N)N>>CSc1ncc(C#N)c(O)n1 | C[O-].[Na+].[Na].C(C)OC=C(C(=O)OCC)C#N.CSC(N)=N>>OC1=NC(=NC=C1C#N)SC | CCO[CH:5]=[C:6]([C:7]#[N:8])[C:9](OCC)=[O:10].[CH3:1][S:2][C:3](=[NH:4])[NH2:11]>>[CH3:1][S:2][c:3]1[n:4][cH:5][c:6]([C:7]#[N:8])[c:9]([OH:10])[n:11]1 | CCOC=C(C#N)C(=O)OCC.CSC(=N)N | CSc1ncc(C#N)c(O)n1 | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 85c723f60fd2e79da5672691165764e8712f29478f65a1fffab3e6fcea655cac | bd32fad25bd03d4c3eaf7cf9714d31932917b50161d45a94baf39b0015694e1b | c1cncnc1 | C-C-O-[CH;D2;+0:1]=[C;H0;D3;+0:2](-[C:3]#[N;D1;H0:4])-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-O-C-C.[C;D1;H3:7]-[#16:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[NH;D1;+0:11]>>[C;D1;H3:7]-[#16:8]-[c;H0;D3;+0:9]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:5](-[OH;D1;+0:6]):[c;H0;D3;+0:2](-[C:3]#[N;D1;H0:4]):[cH;D2;+0:1]:[n;H0;D2;+0:11]:1 | 48 | [{"value": 48.0, "product": "OC1=NC(=NC=C1C#N)SC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a 5° C. solution of 119 g (703 mmol) of freshly distilled ethyl (ethoxymethylene)cyanoacetate in 800 mL of methanol is added 108 g (599 mmol) of 2-methyl-2-thiopseudourea. To this mixture is added a solution of sodium methoxide prepared by dissolving 35.6 g (1.55 mol) of sodium metal in 800 mL of methanol. The solut... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Primary amine.Monosulfide | Aromatic alcohol.Monosulfide | null | c1cncnc1 | c1cncnc1 | HO- | CO | null | 6 | CCOC=C(C#N)C(=O)OCC.CSC(=N)N>CO>CSc1ncc(C#N)c(O)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-085c9f84ee6d4625b6528446c447a9cb | CSc1ncc(C#N)c(O)n1.O=P(Cl)(Cl)Cl>>CSc1ncc(C#N)c(Cl)n1 | OC1=NC(=NC=C1C#N)SC.P(=O)(Cl)(Cl)Cl>>ClC1=NC(=NC=C1C#N)SC | O[c:9]1[c:6]([C:7]#[N:8])[cH:5][n:4][c:3]([S:2][CH3:1])[n:11]1.O=P(Cl)(Cl)[Cl:10]>>[CH3:1][S:2][c:3]1[n:4][cH:5][c:6]([C:7]#[N:8])[c:9]([Cl:10])[n:11]1 | CSc1ncc(C#N)c(O)n1.O=P(Cl)(Cl)Cl | CSc1ncc(C#N)c(Cl)n1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | c34cc3a735ba90a6ebc3a31af86c6a0085713d9dcab569055caa3b8d444bb07d | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1cncnc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4](-[#16:5]):[#7;a:6]:[c:7]:[c:8]:1-[C:9]#[N;D1;H0:10]>>[#16:5]-[c:4]1:[#7;a:3]:[c;H0;D3;+0:2](-[Cl;H0;D1;+0:1]):[c:8](-[C:9]#[N;D1;H0:10]):[c:7]:[#7;a:6]:1 | 60 | [{"value": 60.0, "product": "ClC1=NC(=NC=C1C#N)SC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 48.3 g (289 mmol) of 4-hydroxy-2-(methylthio)-5-pyrimidinecarbonitrile and 150 mL of phosphorus oxychloride is heated at reflux for 3 hours. The reaction mixture is cooled to room temperature, filtered, and the filtrate is concentrated to dryness. The residue is partitioned between dichloromethane and ice ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | null | null | null | CSc1ncc(C#N)c(O)n1.O=P(Cl)(Cl)Cl>>CSc1ncc(C#N)c(Cl)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dea467a11b1a407496123b0c2715f76e | CSc1ncc(C#N)c(Cl)n1.NC1CC2CCC1C2>>CSc1ncc(C#N)c(NC2CC3CCC2C3)n1 | C1CC2CC1CC2N.ClC1=NC(=NC=C1C#N)SC.C(C)N(CC)CC>>C12C(CC(CC1)C2)NC2=NC(=NC=C2C#N)SC | Cl[c:9]1[c:6]([C:7]#[N:8])[cH:5][n:4][c:3]([S:2][CH3:1])[n:18]1.[NH2:10][CH:11]1[CH2:12][CH:13]2[CH2:14][CH2:15][CH:16]1[CH2:17]2>>[CH3:1][S:2][c:3]1[n:4][cH:5][c:6]([C:7]#[N:8])[c:9]([NH:10][CH:11]2[CH2:12][CH:13]3[CH2:14][CH2:15][CH:16]2[CH2:17]3)[n:18]1 | CSc1ncc(C#N)c(Cl)n1.NC1CC2CCC1C2 | CSc1ncc(C#N)c(NC2CC3CCC2C3)n1 | null | null | ClCCl | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(NC2CC3CCC2C3)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6]:[c:7]:1-[C:8]#[N;D1;H0:9].[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13]>>[#16:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:12]-[C:11](-[C:10])-[C:13]):[c:7](-[C:8]#[N;D1;H0:9]):[c:6]:[#7;a:5]:1 | 64 | [{"value": 64.0, "product": "C12C(CC(CC1)C2)NC2=NC(=NC=C2C#N)SC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.4, "product": "C12C(CC(CC1)C2)NC2=NC(=NC=C2C#N)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | To a 0° C. solution of 10.0 g (53.9 mmol) of 4-chloro-2-(methylthio)-5-pyrimidinecarbonitrile in 100 mL of dichloromethane is added 9.0 mL (64.6 mmol) of triethylamine followed by dropwise addition of 7.0 mL (59.3 mmol) of exo-2-aminonorbornane. The reaction mixture is stirred at 0° C. for 2 hours. The resulting precip... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | C1CC2CCC1C2.c1cncnc1 | HCl | ClCCl | 0 | 2 | CSc1ncc(C#N)c(Cl)n1.NC1CC2CCC1C2>ClCCl>CSc1ncc(C#N)c(NC2CC3CCC2C3)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-55f2d7808cfe4103af4db6dfb4d082d3 | CN.CSc1ncc(C#N)c(Cl)n1>>CNc1nc(SC)ncc1C#N | ClC1=NC(=NC=C1C#N)SC.CN>>CNC1=NC(=NC=C1C#N)SC | [CH3:1][NH2:2].Cl[c:3]1[n:4][c:5]([S:6][CH3:7])[n:8][cH:9][c:10]1[C:11]#[N:12]>>[CH3:1][NH:2][c:3]1[n:4][c:5]([S:6][CH3:7])[n:8][cH:9][c:10]1[C:11]#[N:12] | CN.CSc1ncc(C#N)c(Cl)n1 | CNc1nc(SC)ncc1C#N | null | null | C(C)OCC | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cncnc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[C:7]#[N;D1;H0:8].[C;D1;H3:9]-[NH2;D1;+0:10]>>[C;D1;H3:9]-[NH;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1-[C:7]#[N;D1;H0:8] | 81 | [{"value": 81.0, "product": "CNC1=NC(=NC=C1C#N)SC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Through a 5° C. solution of 14.5 g (78.1 mmol) of 4-chloro-2-(methylthio)-5-pyrimidinecarbonitrile in 800 mL of diethyl ether is bubbled methylamine gas for a period of 15 minutes. The reaction mixture is allowed to warm to room temperature, set overnight, and filtered. The solids are washed with diethyl ether, then ef... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | C(C)OCC | null | 8 | CN.CSc1ncc(C#N)c(Cl)n1>C(C)OCC>CNc1nc(SC)ncc1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7ca619c1a25742b3a59e3bbf9e6f86c1 | CSc1ncc(C#N)c(NC2CCCC2)n1>>CSc1ncc(CN)c(NC2CCCC2)n1 | [H-].[H-].[H-].[H-].[Li+].[Al+3].C1(CCCC1)NC1=NC(=NC=C1C#N)SC.S(=O)(=O)([O-])[O-].[NH4+].[NH4+]>>NCC=1C(=NC(=NC1)SC)NC1CCCC1 | [CH3:1][S:2][c:3]1[n:4][cH:5][c:6]([C:7]#[N:8])[c:9]([NH:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[n:16]1>>[CH3:1][S:2][c:3]1[n:4][cH:5][c:6]([CH2:7][NH2:8])[c:9]([NH:10][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[n:16]1 | CSc1ncc(C#N)c(NC2CCCC2)n1 | CSc1ncc(CN)c(NC2CCCC2)n1 | null | null | O1CCCC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1cc(NC2CCCC2)ncn1 | [#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[C;H0;D2;+0:8]#[N;H0;D1;+0:9]>>[#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH2;D2;+0:8]-[NH2;D1;+0:9] | 79 | [{"value": 79.0, "product": "NCC=1C(=NC(=NC1)SC)NC1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.8, "product": "NCC=1C(=NC(=NC1)SC)NC1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a stirred 0° C. suspension of 1.7 g (44.8 mmol) of LAH in 70 mL of tetrahydrofuran is added dropwise a solution of 5.0 g (21.3 mmol) of 4-(cyclopentylamino)-2-(methylthio)-5-pyrimidinecarbonitrile in 250 mL of tetrahydrofuran. The reaction is allowed to warm slowly to room temperature overnight. The mixture is recoo... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1cncnc1.C1CCCC1 | null | O1CCCC1 | null | 0.25 | CSc1ncc(C#N)c(NC2CCCC2)n1>O1CCCC1>CSc1ncc(CN)c(NC2CCCC2)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3d28e01008034d64a935c8ec65db738f | CSc1ncc(C#N)c(NC(C)C)n1>>CSc1ncc(CN)c(NC(C)C)n1 | [H-].[H-].[H-].[H-].[Li+].[Al+3].C(C)(C)NC1=NC(=NC=C1C#N)SC.S(=O)(=O)([O-])[O-].[NH4+].[NH4+]>>NCC=1C(=NC(=NC1)SC)NC(C)C | [CH3:1][S:2][c:3]1[n:4][cH:5][c:6]([C:7]#[N:8])[c:9]([NH:10][CH:11]([CH3:12])[CH3:13])[n:14]1>>[CH3:1][S:2][c:3]1[n:4][cH:5][c:6]([CH2:7][NH2:8])[c:9]([NH:10][CH:11]([CH3:12])[CH3:13])[n:14]1 | CSc1ncc(C#N)c(NC(C)C)n1 | CSc1ncc(CN)c(NC(C)C)n1 | null | null | O1CCCC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1cncnc1 | [#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[C;H0;D2;+0:8]#[N;H0;D1;+0:9]>>[#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH2;D2;+0:8]-[NH2;D1;+0:9] | 82 | [{"value": 82.0, "product": "NCC=1C(=NC(=NC1)SC)NC(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.7, "product": "NCC=1C(=NC(=NC1)SC)NC(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a stirred 0° C. suspension of 5.9 g (156.3 mmol) of LAH in 200 mL of tetrahydrofuran is added dropwise a solution of 15.5 g (74.4 mmol) of 4-(isopropylamino)-2-(methylthio)-5-pyrimidinecarbonitrile in 500 mL of tetrahydrofuran. The reaction is allowed to warm slowly to room temperature overnight. The mixture is reco... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1cncnc1 | null | O1CCCC1 | null | 0.25 | CSc1ncc(C#N)c(NC(C)C)n1>O1CCCC1>CSc1ncc(CN)c(NC(C)C)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-179937a6095240cbb627441f080dc721 | CSc1ncc(C#N)c(NC2CC3CCC2C3)n1>>CSc1ncc(CN)c(NC2CC3CCC2C3)n1 | [H-].[H-].[H-].[H-].[Li+].[Al+3].C12C(CC(CC1)C2)NC2=NC(=NC=C2C#N)SC.S(=O)(=O)([O-])[O-].[NH4+].[NH4+]>>NCC=1C(=NC(=NC1)SC)NC1C2CCC(C1)C2 | [CH3:1][S:2][c:3]1[n:4][cH:5][c:6]([C:7]#[N:8])[c:9]([NH:10][CH:11]2[CH2:12][CH:13]3[CH2:14][CH2:15][CH:16]2[CH2:17]3)[n:18]1>>[CH3:1][S:2][c:3]1[n:4][cH:5][c:6]([CH2:7][NH2:8])[c:9]([NH:10][CH:11]2[CH2:12][CH:13]3[CH2:14][CH2:15][CH:16]2[CH2:17]3)[n:18]1 | CSc1ncc(C#N)c(NC2CC3CCC2C3)n1 | CSc1ncc(CN)c(NC2CC3CCC2C3)n1 | null | null | O1CCCC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | c1cc(NC2CC3CCC2C3)ncn1 | [#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[C;H0;D2;+0:8]#[N;H0;D1;+0:9]>>[#7:1]-[c:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[CH2;D2;+0:8]-[NH2;D1;+0:9] | 68 | [{"value": 68.0, "product": "NCC=1C(=NC(=NC1)SC)NC1C2CCC(C1)C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.3, "product": "NCC=1C(=NC(=NC1)SC)NC1C2CCC(C1)C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a stirred 0° C. suspension of 2.5 g (65.3 mmol) of LAH in 100 mL of tetrahydrofuran is added dropwise a solution of 8.5 g (32.6 mmol) of 4-(bicyclo[2.2.1]hept-2-yl-amino)-2-(methylthio)-5-pyrimidinecarbonitrile in 375 mL of tetrahydrofuran. The reaction is allowed to warm slowly to room temperature overnight. The mi... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1CC2CCC1C2.c1cncnc1 | null | O1CCCC1 | null | 0.25 | CSc1ncc(C#N)c(NC2CC3CCC2C3)n1>O1CCCC1>CSc1ncc(CN)c(NC2CC3CCC2C3)n1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e24d2764068143ee8d95a30d04645eb4 | COc1ccc(N)cc1.CS(=O)c1ncc2c(n1)N(C1CCCC1)C(=O)NC2>>COc1ccc(Nc2ncc3c(n2)N(C2CCCC2)C(=O)NC3)cc1 | C1(CCCC1)N1C(NCC=2C1=NC(=NC2)S(=O)C)=O.COC1=CC=C(C=C1)N.CS(=O)C>>C1(CCCC1)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)OC)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:24][cH:25]1.CS(=O)[c:8]1[n:9][cH:10][c:11]2[c:12]([n:13]1)[N:14]([CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19]1)[C:20](=[O:21])[NH:22][CH2:23]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][c:8]2[n:9][cH:10][c:11]3[c:12]([n:13]2)[N:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[... | COc1ccc(N)cc1.CS(=O)c1ncc2c(n1)N(C1CCCC1)C(=O)NC2 | COc1ccc(Nc2ncc3c(n2)N(C2CCCC2)C(=O)NC3)cc1 | null | null | C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 503cb7f75204c7a84afd0d3fa585f0e9170372f5ca22b55236a348f1949aff4f | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1NCc2cnc(Nc3ccccc3)nc2N1C1CCCC1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[#7;a:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:5]:[c:6] | 24.2 | [{"value": 24.0, "product": "C1(CCCC1)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.2, "product": "C1(CCCC1)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | A solution of 300 mg (1.07 mmol) of 1-cyclopentyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one, 527 mg (4.28 mmol) of p-anisidine, and 1.5 mL of dimethyl sulfoxide is heated at 130° C. for 30 hours, then cooled and diluted with ethyl acetate. The mixture is washed three times with aqueous sodium chl... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)[NH]CNC2 | c1ncc2c(n1)[NH]CNC2 | c1ccccc1.C1CCCC1.c1ncc2c(n1)[NH]CNC2 | Other | C(C)(=O)OCC | null | 3 | COc1ccc(N)cc1.CS(=O)c1ncc2c(n1)N(C1CCCC1)C(=O)NC2>C(C)(=O)OCC>COc1ccc(Nc2ncc3c(n2)N(C2CCCC2)C(=O)NC3)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-509bd9f1df3a469ea279ff706e84076c | CS(=O)c1ncc2c(n1)N(C1CCCC1)C(=O)NC2.Nc1ccc(N2CCCCC2)cc1>>O=C1NCc2cnc(Nc3ccc(N4CCCCC4)cc3)nc2N1C1CCCC1 | NC1=CC=C(C=C1)N1CCCCC1.C1(CCCC1)N1C(NCC=2C1=NC(=NC2)S(=O)C)=O.C12(C(=O)CC(CC1)C2(C)C)CS(=O)(=O)O.O1CCOCC1>>C1(CCCC1)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCCCC2)=O | CS(=O)[c:8]1[n:7][cH:6][c:5]2[c:23]([n:22]1)[N:24]([CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29]1)[C:2](=[O:1])[NH:3][CH2:4]2.[NH2:9][c:10]1[cH:11][cH:12][c:13]([N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[cH:20][cH:21]1>>[O:1]=[C:2]1[NH:3][CH2:4][c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([N:14]4[CH2:15][... | CS(=O)c1ncc2c(n1)N(C1CCCC1)C(=O)NC2.Nc1ccc(N2CCCCC2)cc1 | O=C1NCc2cnc(Nc3ccc(N4CCCCC4)cc3)nc2N1C1CCCC1 | null | null | C(Cl)(Cl)Cl.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 503cb7f75204c7a84afd0d3fa585f0e9170372f5ca22b55236a348f1949aff4f | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1NCc2cnc(Nc3ccc(N4CCCCC4)cc3)nc2N1C1CCCC1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]-[#7:4]):[#7;a:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7:4]-[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:5]:[c:6] | 24 | [{"value": 24.0, "product": "C1(CCCC1)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCCCC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.0, "product": "C1(CCCC1)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCCCC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 377 mg (2.14 mmol) of 1-(4-aminophenyl)piperidine, 300 mg (1.07 mmol) of 1-cyclopentyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one, 745 mg (3.21 mmol) of camphorsulfonic acid, and 2 mL of p-dioxane is heated at 130° C. for 1 hour in a sealed tube. The mixture is cooled and diluted wit... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)[NH]CNC2 | c1ncc2c(n1)[NH]CNC2 | c1ncc2c(n1)[NH]CNC2.c1ccccc1.C1CC[NH]CC1.C1CCCC1 | Other | C(Cl)(Cl)Cl.C(C)(=O)OCC | null | null | CS(=O)c1ncc2c(n1)N(C1CCCC1)C(=O)NC2.Nc1ccc(N2CCCCC2)cc1>C(Cl)(Cl)Cl.C(C)(=O)OCC>O=C1NCc2cnc(Nc3ccc(N4CCCCC4)cc3)nc2N1C1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe860b43c69544fc840aaf097b623f83 | CN1CCN(c2ccc(N)cc2)CC1.CS(=O)c1ncc2c(n1)N(C1CCCC1)C(=O)NC2>>CN1CCN(c2ccc(Nc3ncc4c(n3)N(C3CCCC3)C(=O)NC4)cc2)CC1 | C1(CCCC1)N1C(NCC=2C1=NC(=NC2)S(=O)C)=O.NC1=CC=C(C=C1)N1CCN(CC1)C.FC(C(=O)O)(F)F>>C1(CCCC1)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:27][cH:28]2)[CH2:29][CH2:30]1.CS(=O)[c:11]1[n:12][cH:13][c:14]2[c:15]([n:16]1)[N:17]([CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22]1)[C:23](=[O:24])[NH:25][CH2:26]2>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]... | CN1CCN(c2ccc(N)cc2)CC1.CS(=O)c1ncc2c(n1)N(C1CCCC1)C(=O)NC2 | CN1CCN(c2ccc(Nc3ncc4c(n3)N(C3CCCC3)C(=O)NC4)cc2)CC1 | null | null | C(C)#N.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 503cb7f75204c7a84afd0d3fa585f0e9170372f5ca22b55236a348f1949aff4f | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1NCc2cnc(Nc3ccc(N4CCNCC4)cc3)nc2N1C1CCCC1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:2]:[c:3] | 80 | [{"value": 80.0, "product": "C1(CCCC1)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.5, "product": "C1(CCCC1)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | 2 | HOUR | To a solution of 2.0 g (7.1 mmol) of 1-cyclopentyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 2.7 g (14.3 mmol) of 1-(4-aminophenyl)-4-methylpiperazine in 32 mL of acetonitrile is added 2.75 mL (35.7 mmol) of trifluoroacetic acid. The mixture is heated at 85° C. overnight. The cooled reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)[NH]CNC2 | c1ncc2c(n1)[NH]CNC2 | C1C[NH]CC[NH]1.c1ccccc1.C1CCCC1.c1ncc2c(n1)[NH]CNC2 | Other | C(C)#N.C(C)(=O)OCC | 85 | 2 | CN1CCN(c2ccc(N)cc2)CC1.CS(=O)c1ncc2c(n1)N(C1CCCC1)C(=O)NC2>C(C)#N.C(C)(=O)OCC>CN1CCN(c2ccc(Nc3ncc4c(n3)N(C3CCCC3)C(=O)NC4)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8f8ef3d2b78644d881d49baf3b0135de | CC(C)N1C(=O)NCc2cnc(S(C)=O)nc21.CN1CCN(c2ccc(N)cc2)CC1>>CC(C)N1C(=O)NCc2cnc(Nc3ccc(N4CCN(C)CC4)cc3)nc21 | C(C)(C)N1C(NCC=2C1=NC(=NC2)S(=O)C)=O.NC1=CC=C(C=C1)N1CCN(CC1)C.FC(C(=O)O)(F)F>>C(C)(C)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O | CS(=O)[c:12]1[n:11][cH:10][c:9]2[c:28]([n:27]1)[N:4]([CH:2]([CH3:1])[CH3:3])[C:5](=[O:6])[NH:7][CH2:8]2.[NH2:13][c:14]1[cH:15][cH:16][c:17]([N:18]2[CH2:19][CH2:20][N:21]([CH3:22])[CH2:23][CH2:24]2)[cH:25][cH:26]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[NH:7][CH2:8][c:9]2[cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:1... | CC(C)N1C(=O)NCc2cnc(S(C)=O)nc21.CN1CCN(c2ccc(N)cc2)CC1 | CC(C)N1C(=O)NCc2cnc(Nc3ccc(N4CCN(C)CC4)cc3)nc21 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 503cb7f75204c7a84afd0d3fa585f0e9170372f5ca22b55236a348f1949aff4f | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1NCc2cnc(Nc3ccc(N4CCNCC4)cc3)nc2N1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:2]:[c:3] | 78.5 | [{"value": 78.0, "product": "C(C)(C)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.5, "product": "C(C)(C)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | Prepared from 400 mg (1.57 mmol) of 1-isopropyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one, 600 mg (3.14 mmol) of 1-(4-aminophenyl)-4-methylpiperazine and 605 μL (7.85 mmol) of trifluoroacetic acid in 6.4 mL of acetonitrile. The reaction mixture is heated at 85° C. for 48 hours. After the workup, ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)[NH]CNC2 | c1ncc2c(n1)[NH]CNC2 | c1ncc2c(n1)[NH]CNC2.c1ccccc1.C1C[NH]CC[NH]1 | Other | C(C)#N | 85 | null | CC(C)N1C(=O)NCc2cnc(S(C)=O)nc21.CN1CCN(c2ccc(N)cc2)CC1>C(C)#N>CC(C)N1C(=O)NCc2cnc(Nc3ccc(N4CCN(C)CC4)cc3)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-032065e1bb9c4f3c9e856d61dba1c36b | CC(C)N1C(=O)NCc2cnc(S(C)=O)nc21.Nc1ccc(N2CCC(O)CC2)cc1>>CC(C)N1C(=O)NCc2cnc(Nc3ccc(N4CCC(O)CC4)cc3)nc21 | C(C)(C)N1C(NCC=2C1=NC(=NC2)S(=O)C)=O.NC1=CC=C(C=C1)N1CCC(CC1)O.FC(C(=O)O)(F)F>>OC1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(NC2)=O)C(C)C | CS(=O)[c:12]1[n:11][cH:10][c:9]2[c:28]([n:27]1)[N:4]([CH:2]([CH3:1])[CH3:3])[C:5](=[O:6])[NH:7][CH2:8]2.[NH2:13][c:14]1[cH:15][cH:16][c:17]([N:18]2[CH2:19][CH2:20][CH:21]([OH:22])[CH2:23][CH2:24]2)[cH:25][cH:26]1>>[CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[NH:7][CH2:8][c:9]2[cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:1... | CC(C)N1C(=O)NCc2cnc(S(C)=O)nc21.Nc1ccc(N2CCC(O)CC2)cc1 | CC(C)N1C(=O)NCc2cnc(Nc3ccc(N4CCC(O)CC4)cc3)nc21 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 503cb7f75204c7a84afd0d3fa585f0e9170372f5ca22b55236a348f1949aff4f | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1NCc2cnc(Nc3ccc(N4CCCCC4)cc3)nc2N1 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:2]:[c:3] | 14.9 | [{"value": 13.0, "product": "OC1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(NC2)=O)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 14.9, "product": "OC1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(NC2)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared from 200 mg (0.79 mmol) of 1-isopropyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one, 302 mg (1.57 mmol) of 1-(4-aminophenyl)-4-hydroxypiperidine and 182 μL (2.36 mmol) of trifluoroacetic acid in 3.2 mL of acetonitrile. After the workup, the crude residue is triturated in ethyl acetate/dichl... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)[NH]CNC2 | c1ncc2c(n1)[NH]CNC2 | c1ncc2c(n1)[NH]CNC2.c1ccccc1.C1CC[NH]CC1 | Other | C(C)#N | null | null | CC(C)N1C(=O)NCc2cnc(S(C)=O)nc21.Nc1ccc(N2CCC(O)CC2)cc1>C(C)#N>CC(C)N1C(=O)NCc2cnc(Nc3ccc(N4CCC(O)CC4)cc3)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b934ffe6a7bf40dfa66cbe5b680555f5 | CN1CCN(c2ccc(N)cc2)CC1.CS(=O)c1ncc2c(n1)N(C1CC3CCC1C3)C(=O)NC2>>CN1CCN(c2ccc(Nc3ncc4c(n3)N(C3CC5CCC3C5)C(=O)NC4)cc2)CC1 | C12C(CC(CC1)C2)N2C(NCC=1C2=NC(=NC1)S(=O)C)=O.NC1=CC=C(C=C1)N1CCN(CC1)C.FC(C(=O)O)(F)F>>C12C(CC(CC1)C2)N2C(NCC=1C2=NC(=NC1)NC1=CC=C(C=C1)N1CCN(CC1)C)=O | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:29][cH:30]2)[CH2:31][CH2:32]1.CS(=O)[c:11]1[n:12][cH:13][c:14]2[c:15]([n:16]1)[N:17]([CH:18]1[CH2:19][CH:20]3[CH2:21][CH2:22][CH:23]1[CH2:24]3)[C:25](=[O:26])[NH:27][CH2:28]2>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:... | CN1CCN(c2ccc(N)cc2)CC1.CS(=O)c1ncc2c(n1)N(C1CC3CCC1C3)C(=O)NC2 | CN1CCN(c2ccc(Nc3ncc4c(n3)N(C3CC5CCC3C5)C(=O)NC4)cc2)CC1 | null | null | C(C)#N.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 503cb7f75204c7a84afd0d3fa585f0e9170372f5ca22b55236a348f1949aff4f | 5d96541e7662f23805fb9b1f27c86ee9e32f55f6d2b692c46751dd2fe7aa65a5 | O=C1NCc2cnc(Nc3ccc(N4CCNCC4)cc3)nc2N1C1CC2CCC1C2 | C-S(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]-[#7:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[#7:6]-[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:7]-[c:8](:[c:9]):[c:10]):[#7;a:2]:[c:3] | 63 | [{"value": 63.0, "product": "C12C(CC(CC1)C2)N2C(NCC=1C2=NC(=NC1)NC1=CC=C(C=C1)N1CCN(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.6, "product": "C12C(CC(CC1)C2)N2C(NCC=1C2=NC(=NC1)NC1=CC=C(C=C1)N1CCN(CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 85 | CELSIUS | null | null | To a suspension of 300 mg (0.98 mmol) of 1-bicyclo[2.2.1]hept-2-yl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 374 mg (1.96 mmol) of 1-(4-aminophenyl)-4-methylpiperazine in 4.0 mL of acetonitrile is added 377 μL (4.90 mmol) of trifluoroacetic acid. The mixture is heated at 85° C. overnight. The... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfoxide | Secondary amine | c1ncc2c(n1)[NH]CNC2 | c1ncc2c(n1)[NH]CNC2 | C1CC2CCC1C2.C1C[NH]CC[NH]1.c1ccccc1.c1ncc2c(n1)[NH]CNC2 | Other | C(C)#N.C(C)(=O)OCC | 85 | null | CN1CCN(c2ccc(N)cc2)CC1.CS(=O)c1ncc2c(n1)N(C1CC3CCC1C3)C(=O)NC2>C(C)#N.C(C)(=O)OCC>CN1CCN(c2ccc(Nc3ncc4c(n3)N(C3CC5CCC3C5)C(=O)NC4)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ed0b76cefeb7424982a53a017679755b | CN1CCN(c2ccc(Nc3ncc4c(n3)N(C3CCCC3)C(=O)NC4)cc2)CC1>>CN1CCN(c2ccc(Nc3ncc4cnc(=O)n(C5CCCC5)c4n3)cc2)CC1 | C1(CCCC1)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O.CC(C)([O-])C.[K+]>>C1(CCCC1)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]4[c:25]([n:26]3)[N:19]([CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24]3)[C:17](=[O:18])[NH:16][CH2:15]4)[cH:27][cH:28]2)[CH2:29][CH2:30]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]4[cH:15]... | CN1CCN(c2ccc(Nc3ncc4c(n3)N(C3CCCC3)C(=O)NC4)cc2)CC1 | CN1CCN(c2ccc(Nc3ncc4cnc(=O)n(C5CCCC5)c4n3)cc2)CC1 | null | null | C1CCOC1 | Oxidation | OtherReaction | ccd52238b8edde4c58e81d3111248a38690f9dd739cd9ced3b9818bbb909b6ab | edfb5babe54f953a39f272026e78805b7f2ba5c416c46fa2b81b82d6c069a8fd | O=c1ncc2cnc(Nc3ccc(N4CCNCC4)cc3)nc2n1C1CCCC1 | [C:1]-[C:2](-[N;H0;D3;+0:3]1-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[CH2;D2;+0:7]-[c:8]2:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:2-1)-[C:14]>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[c:13]2:[#7;a:12]:[c:11]:[#7;a:10]:[c:9]:[c:8]:2:[cH;D2;+0:7]:[n;H0;D2;+0:6]:[c;H0;D3;+0:4]:1=[O;D1;H0:5])-[C:14] | 67 | [{"value": 67.0, "product": "C1(CCCC1)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.7, "product": "C1(CCCC1)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared from 150 mg (0.37 mmol) of 1-cyclopentyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 165 mg (1.47 mmol) of potassium tert-butoxide in 6 mL of THF. The dark orange semi-solid is triturated in diethyl ether, and the yellow powder is collected and dried to give 100... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ncc2c(n1)[NH]CNC2 | c1ncc2cncnc2n1 | C1C[NH]CC[NH]1.c1ccccc1.c1ncc2cncnc2n1.C1CCCC1 | null | C1CCOC1 | null | null | CN1CCN(c2ccc(Nc3ncc4c(n3)N(C3CCCC3)C(=O)NC4)cc2)CC1>C1CCOC1>CN1CCN(c2ccc(Nc3ncc4cnc(=O)n(C5CCCC5)c4n3)cc2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ed9dfb12b6bb44668d2e8780d1f64eac | O=C1NCc2cnc(Nc3ccc(N4CCC(O)CC4)cc3)nc2N1C1CCCC1>>O=c1ncc2cnc(Nc3ccc(N4CCC(O)CC4)cc3)nc2n1C1CCCC1 | C1(CCCC1)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCC(CC2)O)=O.CC(C)([O-])C.[K+]>>C1(CCCC1)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCC(CC2)O)=O | [O:1]=[C:2]1[NH:3][CH2:4][c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([N:14]4[CH2:15][CH2:16][CH:17]([OH:18])[CH2:19][CH2:20]4)[cH:21][cH:22]3)[n:23][c:24]2[N:25]1[CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30]1>>[O:1]=[c:2]1[n:3][cH:4][c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([N:14]4[CH2:15][CH2:16... | O=C1NCc2cnc(Nc3ccc(N4CCC(O)CC4)cc3)nc2N1C1CCCC1 | O=c1ncc2cnc(Nc3ccc(N4CCC(O)CC4)cc3)nc2n1C1CCCC1 | null | null | CS(=O)C | Oxidation | OtherReaction | ccd52238b8edde4c58e81d3111248a38690f9dd739cd9ced3b9818bbb909b6ab | edfb5babe54f953a39f272026e78805b7f2ba5c416c46fa2b81b82d6c069a8fd | O=c1ncc2cnc(Nc3ccc(N4CCCCC4)cc3)nc2n1C1CCCC1 | [C:1]-[C:2](-[N;H0;D3;+0:3]1-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[CH2;D2;+0:7]-[c:8]2:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:2-1)-[C:14]>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[c:13]2:[#7;a:12]:[c:11]:[#7;a:10]:[c:9]:[c:8]:2:[cH;D2;+0:7]:[n;H0;D2;+0:6]:[c;H0;D3;+0:4]:1=[O;D1;H0:5])-[C:14] | 32.8 | [{"value": 30.0, "product": "C1(CCCC1)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCC(CC2)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.8, "product": "C1(CCCC1)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCC(CC2)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared from 60 mg (0.15 mmol) of 1-cyclopentyl-7-[4-(4-hydroxypiperidin-1-yl)phenylamino]-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 66 mg (0.58 mmol) of potassium tert-butoxide in 1.5 mL of DMSO. The crude semi-solid residue is triturated in 15 mL of 2:1 diethyl ether/hexane, and the orange amorphous solid i... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ncc2c(n1)[NH]CNC2 | c1ncc2cncnc2n1 | c1ncc2cncnc2n1.c1ccccc1.C1CC[NH]CC1.C1CCCC1 | null | CS(=O)C | null | null | O=C1NCc2cnc(Nc3ccc(N4CCC(O)CC4)cc3)nc2N1C1CCCC1>CS(=O)C>O=c1ncc2cnc(Nc3ccc(N4CCC(O)CC4)cc3)nc2n1C1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-958947793f6f451ea3d2dc94d0df9516 | CCN(CC)CCOc1ccc(Nc2ncc3c(n2)N(C2CCCC2)C(=O)NC3)cc1C>>CCN(CC)CCOc1ccc(Nc2ncc3cnc(=O)n(C4CCCC4)c3n2)cc1C | C1(CCCC1)N1C(NCC=2C1=NC(=NC2)NC2=CC(=C(C=C2)OCCN(CC)CC)C)=O.CC(C)([O-])C.[K+]>>C1(CCCC1)N1C(N=CC=2C1=NC(=NC2)NC2=CC(=C(C=C2)OCCN(CC)CC)C)=O | [CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([NH:13][c:14]2[n:15][cH:16][c:17]3[c:28]([n:29]2)[N:22]([CH:23]2[CH2:24][CH2:25][CH2:26][CH2:27]2)[C:20](=[O:21])[NH:19][CH2:18]3)[cH:30][c:31]1[CH3:32]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([NH:... | CCN(CC)CCOc1ccc(Nc2ncc3c(n2)N(C2CCCC2)C(=O)NC3)cc1C | CCN(CC)CCOc1ccc(Nc2ncc3cnc(=O)n(C4CCCC4)c3n2)cc1C | null | null | CCCCCC.CS(=O)C.COC(C)(C)C | Oxidation | OtherReaction | ccd52238b8edde4c58e81d3111248a38690f9dd739cd9ced3b9818bbb909b6ab | edfb5babe54f953a39f272026e78805b7f2ba5c416c46fa2b81b82d6c069a8fd | O=c1ncc2cnc(Nc3ccccc3)nc2n1C1CCCC1 | [C:1]-[C:2](-[N;H0;D3;+0:3]1-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[CH2;D2;+0:7]-[c:8]2:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:2-1)-[C:14]>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[c:13]2:[#7;a:12]:[c:11]:[#7;a:10]:[c:9]:[c:8]:2:[cH;D2;+0:7]:[n;H0;D2;+0:6]:[c;H0;D3;+0:4]:1=[O;D1;H0:5])-[C:14] | 24.3 | [{"value": 24.0, "product": "C1(CCCC1)N1C(N=CC=2C1=NC(=NC2)NC2=CC(=C(C=C2)OCCN(CC)CC)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.3, "product": "C1(CCCC1)N1C(N=CC=2C1=NC(=NC2)NC2=CC(=C(C=C2)OCCN(CC)CC)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared from 70 mg (0.16 mmol) of 1-cyclopentyl-7-{3-methyl-4-[2-(diethylamino)ethoxy]phenylamino}-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 72 mg (0.58 mmol) of potassium tert-butoxide in 3.0 mL of DMSO. The crude semi-solid residue is dissolved in a mixture of tert-butyl methyl ether and hexane. The solutio... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ncc2c(n1)[NH]CNC2 | c1ncc2cncnc2n1 | c1ccccc1.c1ncc2cncnc2n1.C1CCCC1 | null | CCCCCC.CS(=O)C.COC(C)(C)C | null | null | CCN(CC)CCOc1ccc(Nc2ncc3c(n2)N(C2CCCC2)C(=O)NC3)cc1C>CCCCCC.CS(=O)C.COC(C)(C)C>CCN(CC)CCOc1ccc(Nc2ncc3cnc(=O)n(C4CCCC4)c3n2)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ffbaaa68e8649d6852f4cdccabdf1bb | O=C1NCc2cnc(Nc3ccc(N4CCCC(O)C4)cc3)nc2N1C1CCCC1>>O=c1ncc2cnc(Nc3ccc(N4CCCC(O)C4)cc3)nc2n1C1CCCC1 | C1(CCCC1)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CC(CCC2)O)=O.CC(C)([O-])C.[K+]>>C1(CCCC1)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CC(CCC2)O)=O | [O:1]=[C:2]1[NH:3][CH2:4][c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([N:14]4[CH2:15][CH2:16][CH2:17][CH:18]([OH:19])[CH2:20]4)[cH:21][cH:22]3)[n:23][c:24]2[N:25]1[CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30]1>>[O:1]=[c:2]1[n:3][cH:4][c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([N:14]4[CH2:15][CH2:16... | O=C1NCc2cnc(Nc3ccc(N4CCCC(O)C4)cc3)nc2N1C1CCCC1 | O=c1ncc2cnc(Nc3ccc(N4CCCC(O)C4)cc3)nc2n1C1CCCC1 | null | null | C1CCOC1 | Oxidation | OtherReaction | ccd52238b8edde4c58e81d3111248a38690f9dd739cd9ced3b9818bbb909b6ab | edfb5babe54f953a39f272026e78805b7f2ba5c416c46fa2b81b82d6c069a8fd | O=c1ncc2cnc(Nc3ccc(N4CCCCC4)cc3)nc2n1C1CCCC1 | [C:1]-[C:2](-[N;H0;D3;+0:3]1-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[CH2;D2;+0:7]-[c:8]2:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:2-1)-[C:14]>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[c:13]2:[#7;a:12]:[c:11]:[#7;a:10]:[c:9]:[c:8]:2:[cH;D2;+0:7]:[n;H0;D2;+0:6]:[c;H0;D3;+0:4]:1=[O;D1;H0:5])-[C:14] | 47.8 | [{"value": 45.0, "product": "C1(CCCC1)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CC(CCC2)O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.8, "product": "C1(CCCC1)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CC(CCC2)O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared from 75 mg (0.18 mmol) of 1-cyclopentyl-7-[4-(3-hydroxypiperidin-1-yl)phenylamino]-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 82 mg (0.73 mmol) of potassium tert-butoxide in 4.0 mL of THF. The semi-solid residue is triturated in diethyl ether, and the orange amorphous solid is collected and dried to gi... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ncc2c(n1)[NH]CNC2 | c1ncc2cncnc2n1 | c1ncc2cncnc2n1.c1ccccc1.C1CC[NH]CC1.C1CCCC1 | null | C1CCOC1 | null | null | O=C1NCc2cnc(Nc3ccc(N4CCCC(O)C4)cc3)nc2N1C1CCCC1>C1CCOC1>O=c1ncc2cnc(Nc3ccc(N4CCCC(O)C4)cc3)nc2n1C1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-06945ac2caeb4eccb18008a0474c2c71 | O=C1NCc2cnc(Nc3ccc(-n4cccn4)cc3)nc2N1C1CCCC1>>O=c1ncc2cnc(Nc3ccc(-n4cccn4)cc3)nc2n1C1CCCC1 | FC(C(=O)[O-])(F)F.C1(CCCC1)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2N=CC=C2)=O.CC(C)([O-])C.[K+]>>C1(CCCC1)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2N=CC=C2)=O | [O:1]=[C:2]1[NH:3][CH2:4][c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13](-[n:14]4[cH:15][cH:16][cH:17][n:18]4)[cH:19][cH:20]3)[n:21][c:22]2[N:23]1[CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28]1>>[O:1]=[c:2]1[n:3][cH:4][c:5]2[cH:6][n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13](-[n:14]4[cH:15][cH:16][cH:17][n:18]4)[cH:1... | O=C1NCc2cnc(Nc3ccc(-n4cccn4)cc3)nc2N1C1CCCC1 | O=c1ncc2cnc(Nc3ccc(-n4cccn4)cc3)nc2n1C1CCCC1 | null | null | C1CCOC1 | Oxidation | OtherReaction | ccd52238b8edde4c58e81d3111248a38690f9dd739cd9ced3b9818bbb909b6ab | edfb5babe54f953a39f272026e78805b7f2ba5c416c46fa2b81b82d6c069a8fd | O=c1ncc2cnc(Nc3ccc(-n4cccn4)cc3)nc2n1C1CCCC1 | [C:1]-[C:2](-[N;H0;D3;+0:3]1-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[CH2;D2;+0:7]-[c:8]2:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:2-1)-[C:14]>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[c:13]2:[#7;a:12]:[c:11]:[#7;a:10]:[c:9]:[c:8]:2:[cH;D2;+0:7]:[n;H0;D2;+0:6]:[c;H0;D3;+0:4]:1=[O;D1;H0:5])-[C:14] | 40 | [{"value": 40.0, "product": "C1(CCCC1)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2N=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared from 100 mg (0.20 mmol) of the trifluoroacetate salt of 1-cyclopentyl-7-[4-(pyrazol-1-yl)phenylamino]-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 115 mg (1.02 mmol) of potassium tert-butoxide in 5.0 mL of THF. The semi-solid residue is triturated in diethyl ether, and the orange amorphous solid is colle... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ncc2c(n1)[NH]CNC2 | c1ncc2cncnc2n1 | c1ncc2cncnc2n1.c1ccccc1.c1cn[nH]c1.C1CCCC1 | null | C1CCOC1 | null | null | O=C1NCc2cnc(Nc3ccc(-n4cccn4)cc3)nc2N1C1CCCC1>C1CCOC1>O=c1ncc2cnc(Nc3ccc(-n4cccn4)cc3)nc2n1C1CCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ce0bb68876a24fa7a7b71b3091954b4b | CC(C)N1C(=O)NCc2cnc(Nc3ccc(N4CCN(C)CC4)cc3)nc21>>CC(C)n1c(=O)ncc2cnc(Nc3ccc(N4CCN(C)CC4)cc3)nc21 | C(C)(C)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O.CC(C)([O-])C.[K+]>>C(C)(C)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O | [CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[NH:7][CH2:8][c:9]2[cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][c:17]([N:18]4[CH2:19][CH2:20][N:21]([CH3:22])[CH2:23][CH2:24]4)[cH:25][cH:26]3)[n:27][c:28]21>>[CH3:1][CH:2]([CH3:3])[n:4]1[c:5](=[O:6])[n:7][cH:8][c:9]2[cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][c:17]([N:... | CC(C)N1C(=O)NCc2cnc(Nc3ccc(N4CCN(C)CC4)cc3)nc21 | CC(C)n1c(=O)ncc2cnc(Nc3ccc(N4CCN(C)CC4)cc3)nc21 | null | null | O1CCCC1 | Oxidation | OtherReaction | ccd52238b8edde4c58e81d3111248a38690f9dd739cd9ced3b9818bbb909b6ab | edfb5babe54f953a39f272026e78805b7f2ba5c416c46fa2b81b82d6c069a8fd | O=c1ncc2cnc(Nc3ccc(N4CCNCC4)cc3)nc2[nH]1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[N;H0;D3;+0:4]1-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[CH2;D2;+0:8]-[c:9]2:[c:10]:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:2-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[n;H0;D3;+0:4]1:[c:14]2:[#7;a:13]:[c:12]:[#7;a:11]:[c:10]:[c:9]:2:[cH;D2;+0:8]:[n;H0;D2;+0:7]:[c;H0;D3;+0:5]:1=[O;D1;H0:6] | 68.4 | [{"value": 68.0, "product": "C(C)(C)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.4, "product": "C(C)(C)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCN(CC2)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared from 200 mg (0.52 mmol) of 1-isopropyl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 235 mg (2.10 mmol) of potassium tert-butoxide in 10 mL of tetrahydrofuran. The semi-solid is triturated in 14 mL of 1:1 diethyl ether/hexane, and the powder is collected and dried... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ncc2c(n1)[NH]CNC2 | c1ncc2cncnc2n1 | c1ncc2cncnc2n1.c1ccccc1.C1C[NH]CC[NH]1 | null | O1CCCC1 | null | null | CC(C)N1C(=O)NCc2cnc(Nc3ccc(N4CCN(C)CC4)cc3)nc21>O1CCCC1>CC(C)n1c(=O)ncc2cnc(Nc3ccc(N4CCN(C)CC4)cc3)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b949ae9160ae4c59ae38aaabb1cfeb00 | CC(C)N1C(=O)NCc2cnc(Nc3ccc(N4CCC(N(C)C)CC4)cc3)nc21>>CC(C)n1c(=O)ncc2cnc(Nc3ccc(N4CCC(N(C)C)CC4)cc3)nc21 | CN(C1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(NC2)=O)C(C)C)C.FC(C(=O)O)(F)F.CC(C)([O-])C.[K+]>>CN(C1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(N=C2)=O)C(C)C)C | [CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[NH:7][CH2:8][c:9]2[cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][c:17]([N:18]4[CH2:19][CH2:20][CH:21]([N:22]([CH3:23])[CH3:24])[CH2:25][CH2:26]4)[cH:27][cH:28]3)[n:29][c:30]21>>[CH3:1][CH:2]([CH3:3])[n:4]1[c:5](=[O:6])[n:7][cH:8][c:9]2[cH:10][n:11][c:12]([NH:13][c:14]3[cH:15]... | CC(C)N1C(=O)NCc2cnc(Nc3ccc(N4CCC(N(C)C)CC4)cc3)nc21 | CC(C)n1c(=O)ncc2cnc(Nc3ccc(N4CCC(N(C)C)CC4)cc3)nc21 | null | null | O1CCCC1 | Oxidation | OtherReaction | ccd52238b8edde4c58e81d3111248a38690f9dd739cd9ced3b9818bbb909b6ab | edfb5babe54f953a39f272026e78805b7f2ba5c416c46fa2b81b82d6c069a8fd | O=c1ncc2cnc(Nc3ccc(N4CCCCC4)cc3)nc2[nH]1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[N;H0;D3;+0:4]1-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[CH2;D2;+0:8]-[c:9]2:[c:10]:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:2-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[n;H0;D3;+0:4]1:[c:14]2:[#7;a:13]:[c:12]:[#7;a:11]:[c:10]:[c:9]:2:[cH;D2;+0:8]:[n;H0;D2;+0:7]:[c;H0;D3;+0:5]:1=[O;D1;H0:6] | 19 | [{"value": 18.0, "product": "CN(C1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(N=C2)=O)C(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 19.0, "product": "CN(C1CCN(CC1)C1=CC=C(C=C1)NC1=NC=C2C(=N1)N(C(N=C2)=O)C(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | Prepared from 200 mg (0.31 mmol) of 7-{4-[4-(dimethylamino)piperidin-1-yl]phenylamino}-1-isopropyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one, trifluoroacetic acid and 211 mg (1.88 mmol) of potassium tert-butoxide in 7 mL of tetrahydrofuran. The reaction mixture is stirred for 48 hours, and the workup is done as de... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ncc2c(n1)[NH]CNC2 | c1ncc2cncnc2n1 | c1ncc2cncnc2n1.c1ccccc1.C1CC[NH]CC1 | null | O1CCCC1 | null | 48 | CC(C)N1C(=O)NCc2cnc(Nc3ccc(N4CCC(N(C)C)CC4)cc3)nc21>O1CCCC1>CC(C)n1c(=O)ncc2cnc(Nc3ccc(N4CCC(N(C)C)CC4)cc3)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-081d1b9d44ad4a7fb60944f12b382cd7 | CC(C)N1C(=O)NCc2cnc(Nc3ccc(-n4cccn4)cc3)nc21>>CC(C)n1c(=O)ncc2cnc(Nc3ccc(-n4cccn4)cc3)nc21 | CC(C)([O-])C.[K+].C(C)(C)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2N=CC=C2)=O.FC(C(=O)O)(F)F.CC(C)([O-])C.[K+]>>C(C)(C)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2N=CC=C2)=O | [CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[NH:7][CH2:8][c:9]2[cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][c:17](-[n:18]4[cH:19][cH:20][cH:21][n:22]4)[cH:23][cH:24]3)[n:25][c:26]21>>[CH3:1][CH:2]([CH3:3])[n:4]1[c:5](=[O:6])[n:7][cH:8][c:9]2[cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][c:17](-[n:18]4[cH:19][cH:20][... | CC(C)N1C(=O)NCc2cnc(Nc3ccc(-n4cccn4)cc3)nc21 | CC(C)n1c(=O)ncc2cnc(Nc3ccc(-n4cccn4)cc3)nc21 | null | null | O1CCCC1 | Oxidation | OtherReaction | ccd52238b8edde4c58e81d3111248a38690f9dd739cd9ced3b9818bbb909b6ab | edfb5babe54f953a39f272026e78805b7f2ba5c416c46fa2b81b82d6c069a8fd | O=c1ncc2cnc(Nc3ccc(-n4cccn4)cc3)nc2[nH]1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[N;H0;D3;+0:4]1-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[CH2;D2;+0:8]-[c:9]2:[c:10]:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:2-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[n;H0;D3;+0:4]1:[c:14]2:[#7;a:13]:[c:12]:[#7;a:11]:[c:10]:[c:9]:2:[cH;D2;+0:8]:[n;H0;D2;+0:7]:[c;H0;D3;+0:5]:1=[O;D1;H0:6] | 77.4 | [{"value": 73.0, "product": "C(C)(C)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2N=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.4, "product": "C(C)(C)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2N=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | Prepared from 150 mg (0.32 mmol) of 1-isopropyl-7-[4-(pyrazol-1-yl)phenylamino]-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one, trifluoroacetic acid and 218 mg (1.94 mmol) of potassium tert-butoxide in 10 mL of tetrahydrofuran. The reaction mixture is stirred for 48 hours, 50 mg (0.44 mmol) of potassium tert-butoxide i... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ncc2c(n1)[NH]CNC2 | c1ncc2cncnc2n1 | c1ncc2cncnc2n1.c1ccccc1.c1cn[nH]c1 | null | O1CCCC1 | null | 48 | CC(C)N1C(=O)NCc2cnc(Nc3ccc(-n4cccn4)cc3)nc21>O1CCCC1>CC(C)n1c(=O)ncc2cnc(Nc3ccc(-n4cccn4)cc3)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f63025092e0b449285a8865782de87f3 | CC(C)N1C(=O)NCc2cnc(Nc3ccc(N4CCC(CCCN5CCOCC5)CC4)cc3)nc21>>CC(C)n1c(=O)ncc2cnc(Nc3ccc(N4CCC(CCCN5CCOCC5)CC4)cc3)nc21 | C(C)(C)N1C(NCC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCC(CC2)CCCN2CCOCC2)=O.CC(C)([O-])C.[K+].CC(C)([O-])C.[K+]>>C(C)(C)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCC(CC2)CCCN2CCOCC2)=O | [CH3:1][CH:2]([CH3:3])[N:4]1[C:5](=[O:6])[NH:7][CH2:8][c:9]2[cH:10][n:11][c:12]([NH:13][c:14]3[cH:15][cH:16][c:17]([N:18]4[CH2:19][CH2:20][CH:21]([CH2:22][CH2:23][CH2:24][N:25]5[CH2:26][CH2:27][O:28][CH2:29][CH2:30]5)[CH2:31][CH2:32]4)[cH:33][cH:34]3)[n:35][c:36]21>>[CH3:1][CH:2]([CH3:3])[n:4]1[c:5](=[O:6])[n:7][cH:8][... | CC(C)N1C(=O)NCc2cnc(Nc3ccc(N4CCC(CCCN5CCOCC5)CC4)cc3)nc21 | CC(C)n1c(=O)ncc2cnc(Nc3ccc(N4CCC(CCCN5CCOCC5)CC4)cc3)nc21 | null | null | O1CCCC1.C(C)OCC | Oxidation | OtherReaction | ccd52238b8edde4c58e81d3111248a38690f9dd739cd9ced3b9818bbb909b6ab | edfb5babe54f953a39f272026e78805b7f2ba5c416c46fa2b81b82d6c069a8fd | O=c1ncc2cnc(Nc3ccc(N4CCC(CCCN5CCOCC5)CC4)cc3)nc2[nH]1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[N;H0;D3;+0:4]1-[C;H0;D3;+0:5](=[O;D1;H0:6])-[NH;D2;+0:7]-[CH2;D2;+0:8]-[c:9]2:[c:10]:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:2-1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])-[n;H0;D3;+0:4]1:[c:14]2:[#7;a:13]:[c:12]:[#7;a:11]:[c:10]:[c:9]:2:[cH;D2;+0:8]:[n;H0;D2;+0:7]:[c;H0;D3;+0:5]:1=[O;D1;H0:6] | 88.5 | [{"value": 85.0, "product": "C(C)(C)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCC(CC2)CCCN2CCOCC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.5, "product": "C(C)(C)N1C(N=CC=2C1=NC(=NC2)NC2=CC=C(C=C2)N2CCC(CC2)CCCN2CCOCC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Prepared from 100 mg (0.20 mmol) of 1-isopropyl-7-{4-[4-(3-(morpholin-4-yl)propyl)piperidin-1-yl]phenylamino}-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one and 88.5 mg (0.79 mmol) of potassium tert-butoxide in 10 mL of tetrahydrofuran. The reaction mixture is stirred overnight, 88.5 mg (0.79 mmol) of potassium tert-bu... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ncc2c(n1)[NH]CNC2 | c1ncc2cncnc2n1 | c1ncc2cncnc2n1.c1ccccc1.C1CC[NH]CC1.C1COCC[NH]1 | null | O1CCCC1.C(C)OCC | null | 8 | CC(C)N1C(=O)NCc2cnc(Nc3ccc(N4CCC(CCCN5CCOCC5)CC4)cc3)nc21>O1CCCC1.C(C)OCC>CC(C)n1c(=O)ncc2cnc(Nc3ccc(N4CCC(CCCN5CCOCC5)CC4)cc3)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-47b4f8d2ecf24d84863a2160783fc179 | CN1CCN(c2ccc(Nc3ncc4c(n3)N(C3CC5CCC3C5)C(=O)NC4)cc2)CC1>>CN1CCN(c2ccc(Nc3ncc4cnc(=O)n(C5CC6CCC5C6)c4n3)cc2)CC1 | C12C(CC(CC1)C2)N2C(NCC=1C2=NC(=NC1)NC1=CC=C(C=C1)N1CCN(CC1)C)=O.CC(C)([O-])C.[K+]>>C12C(CC(CC1)C2)N2C(N=CC=1C2=NC(=NC1)NC1=CC=C(C=C1)N1CCN(CC1)C)=O | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:13][c:14]4[c:27]([n:28]3)[N:19]([CH:20]3[CH2:21][CH:22]5[CH2:23][CH2:24][CH:25]3[CH2:26]5)[C:17](=[O:18])[NH:16][CH2:15]4)[cH:29][cH:30]2)[CH2:31][CH2:32]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]([NH:10][c:11]3[n:12][cH:1... | CN1CCN(c2ccc(Nc3ncc4c(n3)N(C3CC5CCC3C5)C(=O)NC4)cc2)CC1 | CN1CCN(c2ccc(Nc3ncc4cnc(=O)n(C5CC6CCC5C6)c4n3)cc2)CC1 | null | null | O1CCCC1 | Oxidation | OtherReaction | ccd52238b8edde4c58e81d3111248a38690f9dd739cd9ced3b9818bbb909b6ab | edfb5babe54f953a39f272026e78805b7f2ba5c416c46fa2b81b82d6c069a8fd | O=c1ncc2cnc(Nc3ccc(N4CCNCC4)cc3)nc2n1C1CC2CCC1C2 | [C:1]-[C:2](-[N;H0;D3;+0:3]1-[C;H0;D3;+0:4](=[O;D1;H0:5])-[NH;D2;+0:6]-[CH2;D2;+0:7]-[c:8]2:[c:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:2-1)-[C:14]>>[C:1]-[C:2](-[n;H0;D3;+0:3]1:[c:13]2:[#7;a:12]:[c:11]:[#7;a:10]:[c:9]:[c:8]:2:[cH;D2;+0:7]:[n;H0;D2;+0:6]:[c;H0;D3;+0:4]:1=[O;D1;H0:5])-[C:14] | 70.5 | [{"value": 70.0, "product": "C12C(CC(CC1)C2)N2C(N=CC=1C2=NC(=NC1)NC1=CC=C(C=C1)N1CCN(CC1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.5, "product": "C12C(CC(CC1)C2)N2C(N=CC=1C2=NC(=NC1)NC1=CC=C(C=C1)N1CCN(CC1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | Prepared from 200 mg (0.46 mmol) of 1-bicyclo[2.2.1]hept-2-yl-7-[4-(4-methylpiperazin-1-yl)phenylamino]-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one, exo and 207 mg (1.84 mmol) of potassium tert-butoxide in 10 mL of tetrahydrofuran. The reaction mixture is stirred for 48 hours. After the workup, the semi-solid is tri... | 10.6084/m9.figshare.5104873.v1 | null | Urea | null | c1ncc2c(n1)[NH]CNC2 | c1ncc2cncnc2n1 | C1CC2CCC1C2.C1C[NH]CC[NH]1.c1ccccc1.c1ncc2cncnc2n1 | null | O1CCCC1 | null | 48 | CN1CCN(c2ccc(Nc3ncc4c(n3)N(C3CC5CCC3C5)C(=O)NC4)cc2)CC1>O1CCCC1>CN1CCN(c2ccc(Nc3ncc4cnc(=O)n(C5CC6CCC5C6)c4n3)cc2)CC1 |
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