dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-69620ec491364bf69d7ad8a18f9b26bf | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.Clc1nccnc1Cl>>CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCOc2nccnc2Cl)CC1 | O.[H-].[Na+].C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(=NC=CN1)OCCO.ClC1=NC=CN=C1Cl>>ClC=1C(=NC=CN1)OCCOC=1C(=NC=CN1)N1CCN(CC1)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[n:13][cH:14][cH:15][n:16][c:17]2[O:18][CH2:19][CH2:20][OH:21])[CH2:29][CH2:30]1.Cl[c:22]1[n:23][cH:24][cH:25][n:26][c:27]1[Cl:28]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[n:13][cH:14][cH:15][n... | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.Clc1nccnc1Cl | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCOc2nccnc2Cl)CC1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8088ac3623a2ee47f375f73ca665bec9cf80b1384463e6e2f03125aecbcea517 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1cnc(OCCOc2nccnc2N2CCNCC2)cn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7] | 61.2 | [{"value": 61.0, "product": "ClC=1C(=NC=CN1)OCCOC=1C(=NC=CN1)N1CCN(CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.2, "product": "ClC=1C(=NC=CN1)OCCOC=1C(=NC=CN1)N1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 8 | HOUR | NaH (50% in mineral oil; 0.153 g, 3.50 mmol) was added to a stirred solution of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol (1.00 g, 3.08 mmol; prepared in Example 52, Step 2) and 2,3-dichloropyrazine (1.0 g, 6.71 mmol) in dioxane (10 mL). The reaction was stirred in a sealed tube at 100° C. overn... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cnccn1 | c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1.c1cnccn1 | HCl | O1CCOCC1 | 100 | 8 | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCO)CC1.Clc1nccnc1Cl>O1CCOCC1>CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCOc2nccnc2Cl)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1c37d26045e8497b9cc63392d9a6114a | C[O-].OCCOc1cccnc1Br>>COc1ncccc1OCCO | BrC1=NC=CC=C1OCCO.C[O-].[Na+]>>OCCOC=1C(=NC=CC1)OC | [CH3:1][O-:2].Br[c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][CH2:11][OH:12]>>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][CH2:11][OH:12] | C[O-].OCCOc1cccnc1Br | COc1ncccc1OCCO | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 600484490705932a09b3fac6538a42c6f3fc156ab44a4ea0bbd020dd3eafd6ff | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1ccncc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#8:5]):[c:6].[C;D1;H3:7]-[O-;H0;D1:8]>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:8]-[C;D1;H3:7]):[#7;a:2]:[c:3] | 45 | [{"value": 45.0, "product": "OCCOC=1C(=NC=CC1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.7, "product": "OCCOC=1C(=NC=CC1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of the product obtained in Step 1 (2.33 g, 10.7 mmol) and NaOMe (0.634 mg, 11.8 mmol) in MeOH (50 mL) was refluxed overnight. The reaction mixture was filtered and concentrated. The residue was purified by column chromatography on silica, using CH2Cl2/MeOH/heptane (4:1:5) as eluent, to give 0.81 g (45%) of th... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1 | Br- | CO | null | null | C[O-].OCCOc1cccnc1Br>CO>COc1ncccc1OCCO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fe13deb2f8f244b88eeb50d6b6084223 | C[C@@H]1CN(C(c2ccccc2)(c2ccccc2)c2ccccc2)CCN1.Clc1nccnc1Cl>>C[C@@H]1CNCCN1c1nccnc1Cl | C(Cl)(Cl)Cl.CCO.C[C@@H]1CN(CCN1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.ClC1=NC=CN=C1Cl.C(=O)([O-])[O-].[K+].[K+]>>ClC=1C(=NC=CN1)N1[C@@H](CNCC1)C | c1ccc(C(c2ccccc2)(c2ccccc2)[N:4]2[CH2:3][C@@H:2]([CH3:1])[NH:7][CH2:6][CH2:5]2)cc1.Cl[c:8]1[n:9][cH:10][cH:11][n:12][c:13]1[Cl:14]>>[CH3:1][C@@H:2]1[CH2:3][NH:4][CH2:5][CH2:6][N:7]1[c:8]1[n:9][cH:10][cH:11][n:12][c:13]1[Cl:14] | C[C@@H]1CN(C(c2ccccc2)(c2ccccc2)c2ccccc2)CCN1.Clc1nccnc1Cl | C[C@@H]1CNCCN1c1nccnc1Cl | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | a9eb66e8dbd1d24aca814a8b35622449727e860aa374e764e270d6d462ef3f42 | 5c70578d0819c8a1731196f6e967b1ca081ac9fc97f879ecb5b3f5b29f334150 | c1cnc(N2CCNCC2)cn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[Cl;D1;H0:7].[C;D1;H3:8]-[C:9]1-[C:10]-[N;H0;D3;+0:11](-C(-c2:c:c:c:c:c:2)(-c2:c:c:c:c:c:2)-c2:c:c:c:c:c:2)-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[C;D1;H3:8]-[C:9]1-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-[N;H0;D3;+0:14]-1-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:... | 66 | [{"value": 66.0, "product": "ClC=1C(=NC=CN1)N1[C@@H](CNCC1)C", "details": "PERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | 30 | MINUTE | A mixture of the product obtained in Step 1 above, 2,3-dichloropyrazine (154 g, 1.00 mmol) and K2CO3 (160 g, 1.20 mol) in DMF (1 L) was heated at 110° C. for 20 h with vigorous stirring. (TLC monitoring system: CHCl3: EtOH (20:1); silica). The mixture was cooled and poured slowly into water (6 L) with stirring. The sol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine.Tertiary amine | Secondary amine.Tertiary amine | c1ccccc1.c1ccccc1.c1ccccc1.C1C[NH]CCN1.c1cnccn1 | C1C[NH]CCN1.c1cnccn1 | C1C[NH]CCN1.c1cnccn1 | HCl | O.CN(C)C=O | 110 | 0.5 | C[C@@H]1CN(C(c2ccccc2)(c2ccccc2)c2ccccc2)CCN1.Clc1nccnc1Cl>O.CN(C)C=O>C[C@@H]1CNCCN1c1nccnc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-091c8811c9fa4cf69a2d9d1e364959ff | C[S-].OCCOc1cccnc1Cl>>CSc1ncccc1OCCO | C[S-].[Na+].ClC1=NC=CC=C1OCCO>>CSC1=NC=CC=C1OCCO | [CH3:1][S-:2].Cl[c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][CH2:11][OH:12]>>[CH3:1][S:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[O:9][CH2:10][CH2:11][OH:12] | C[S-].OCCOc1cccnc1Cl | CSc1ncccc1OCCO | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | a043117f5ac6655ea3d4f71b77392fbb346566d5ecbe0b9ffd7138c05f760a35 | 1813ae14fbd9cacead4dcfaf9efbd2467a19b3e216836766b78aa6647dcfb48a | c1ccncc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#8:5]):[c:6].[C;D1;H3:7]-[S-;H0;D1:8]>>[#8:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[S;H0;D2;+0:8]-[C;D1;H3:7]):[#7;a:2]:[c:3] | 37.8 | [{"value": 36.0, "product": "CSC1=NC=CC=C1OCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.8, "product": "CSC1=NC=CC=C1OCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a suspension of sodium thiomethoxide (3.01 g, 42.9 mmol) in dry DMF (30 mL) was 2-[(2-chloro-3-pyridinyl)oxy]ethanol (7.82 g, 45.1 mmol, from Example 193, Step 1) added and the reaction mixture was stirred at ambient temperature for 1 h. The solvent was removed under reduced pressure and the residue was partitioned ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Monosulfide | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | CN(C)C=O | null | 1 | C[S-].OCCOc1cccnc1Cl>CN(C)C=O>CSc1ncccc1OCCO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f1cb25eb303a4001b2704b07737cf170 | CC(C)(C)[Si](C)(C)Cl.OCCOc1cccnc1Br>>CC(C)(C)[Si](C)(C)OCCOc1cccnc1Br | C[Si](C(C)(C)C)(C)Cl.BrC1=NC=CC=C1OCCO.N1C=NC=C1>>BrC1=NC=CC=C1OCCO[Si](C)(C)C(C)(C)C | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][n:16][c:17]1[Br:18]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][O:11][c:12]1[cH:13][cH:14][cH:15][n:16][c:17]1[Br:18] | CC(C)(C)[Si](C)(C)Cl.OCCOc1cccnc1Br | CC(C)(C)[Si](C)(C)OCCOc1cccnc1Br | null | null | CN(C)C=O.[OH-].[Na+] | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | c1ccncc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[C:8]-[C:9]-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7] | null | [] | null | null | 2 | HOUR | A solution of dimethyl-t-butylsilyl chloride (11.1 g, 74 mmol) in DMF (30 mL) was added to a suspension of 2-bromo-3-(2-hydroxyethoxy)pyridine (15.3 g, 70 mmol; obtained in Example 191, Step 1) and imidazole (10.0 g, 147 mmol) in DMF (30 mL). The reaction mixture was stirred at ambient temperature for 2 h, diluted with... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccncc1 | HCl | CN(C)C=O.[OH-].[Na+] | null | 2 | CC(C)(C)[Si](C)(C)Cl.OCCOc1cccnc1Br>CN(C)C=O.[OH-].[Na+]>CC(C)(C)[Si](C)(C)OCCOc1cccnc1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-31743a51b6504dc4aba84a0f0347480d | CC(C)(C)[Si](C)(C)OCCOc1cccnc1Br.CCO>>CCOc1ncccc1OCCO | BrC1=NC=CC=C1OCCO[Si](C)(C)C(C)(C)C.[O-]CC.[Na+].CCO>>C(C)OC1=NC=CC=C1OCCO | CC(C)(C)[Si](C)(C)[O:13][CH2:12][CH2:11][O:10][c:9]1[c:4](Br)[n:5][cH:6][cH:7][cH:8]1.[CH3:1][CH2:2][OH:3]>>[CH3:1][CH2:2][O:3][c:4]1[n:5][cH:6][cH:7][cH:8][c:9]1[O:10][CH2:11][CH2:12][OH:13] | CC(C)(C)[Si](C)(C)OCCOc1cccnc1Br.CCO | CCOc1ncccc1OCCO | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f117966458f382029b157cde8b0bf9401f9660eea179a83a9a7113216473521f | f216e281e35fe518b2085df6af208cbe54ed366b8463456b519ba975028ae7ec | c1ccncc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#8:5]-[C:6]-[C:7]-[O;H0;D2;+0:8]-[Si](-C)(-C)-C(-C)(-C)-C):[c:9].[C;D1;H3:10]-[C:11]-[OH;D1;+0:12]>>[C;D1;H3:10]-[C:11]-[O;H0;D2;+0:12]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[#8:5]-[C:6]-[C:7]-[OH;D1;+0:8]):[c:9] | 41 | [{"value": 41.0, "product": "C(C)OC1=NC=CC=C1OCCO", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | The product obtained in Step 1 above (13.2 g, 39.7 mmol) was added to sodium ethoxide in EtOH [prepared from Na (10.5 g, 457 mmol) and EtOH (200 mL)]. The resulting mixture was heated at 70° C. overnight. After cooling to ambient temperature, the reaction mixture was diluted with ice water (0.8 L) and extracted with Et... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol.TMS ether protective group | Ether.Primary alcohol | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr | null | 70 | null | CC(C)(C)[Si](C)(C)OCCOc1cccnc1Br.CCO>>CCOc1ncccc1OCCO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d018fec252db4e5a9e88142adb2f4a73 | C=O.COc1ccc(N)cc1O>>COc1ccc(N(C)C)cc1O | [H-].NC=1C=CC(=C(C1)O)OC.C=O.C(#N)[BH3-].[Na+]>>CN(C=1C=CC(=C(C1)O)OC)C | O=[CH2:8].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:10][c:11]1[OH:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH3:8])[CH3:9])[cH:10][c:11]1[OH:12] | C=O.COc1ccc(N)cc1O | COc1ccc(N(C)C)cc1O | null | null | C(C)(=O)O.C(C)O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Primary Amine Methylation | 5bc40be4d4b4346801fbfcec480fec37de3ff2eecebe2990b3686fa4792d12b6 | 5cdbf447f632627824e84e0bcac2293ea9ebd70c19b0d56dea90691653b444c7 | c1ccccc1 | O=[CH2;D1;+0:1].[NH2;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[C;D1;H3:6]-[N;H0;D3;+0:2](-[CH3;D1;+0:1])-[c:3](:[c:4]):[c:5] | 20 | [{"value": 20.0, "product": "CN(C=1C=CC(=C(C1)O)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a stirred solution of 5-amino-2-methoxyphenol (5.0 g, 36 mmol) in ethanol (250 mL), was added 33% formaldehyde (4×1.5 mL at times 0, 60 min, 140 min and 185 min) and sodium cyanoborohydride (4×0.8 g, at times 30 min, 120 min, 165 min and 210 min). After each addition of the hydride, pH was adjusted to ˜6 using aceti... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Primary amine | Tertiary amine | null | null | c1ccccc1 | null | C(C)(=O)O.C(C)O | null | 2 | C=O.COc1ccc(N)cc1O>C(C)(=O)O.C(C)O>COc1ccc(N(C)C)cc1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3555db0f151642c7b45cc764313fca0f | C1CNCCN1.Clc1nsnc1Cl>>Cl.Clc1nsnc1N1CCNCC1 | ClC1=NSN=C1Cl.O.O.O.O.O.O.N1CCNCC1.[OH-].[Na+]>>Cl.ClC1=NSN=C1N1CCNCC1 | [NH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1.[Cl:1][c:7]1[c:3]([Cl:2])[n:4][s:5][n:6]1>>[ClH:1].[Cl:2][c:3]1[n:4][s:5][n:6][c:7]1[N:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1 | C1CNCCN1.Clc1nsnc1Cl | Cl.Clc1nsnc1N1CCNCC1 | null | null | [Cl-].[Na+].O.CN(C)C=O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | adffb830a4483326d742b7dc1e45dc4b03e33fa8db2a297e07883f222e2c68d3 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1nsnc1N1CCNCC1 | [#7:1]1-[C:2]-[C:3]-[NH;D2;+0:4]-[C:5]-[C:6]-1.[Cl;D1;H0:7]-[c:8]1:[#7;a:9]:[#16;a:10]:[#7;a:11]:[c;H0;D3;+0:12]:1-[Cl;H0;D1;+0:13]>>[Cl;D1;H0:7]-[c:8]1:[#7;a:9]:[#16;a:10]:[#7;a:11]:[c;H0;D3;+0:12]:1-[N;H0;D3;+0:4]1-[C:5]-[C:6]-[#7:1]-[C:2]-[C:3]-1.[ClH;D0;+0:13] | 89 | [{"value": 52.0, "product": "Cl.ClC1=NSN=C1N1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.0, "product": "Cl.ClC1=NSN=C1N1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | A mixture of 3,4-dichloro-1,2,5-thiadiazole (4.00 g, 25.8 mmol) and piperazine hexahydrate (25.0 g, 130 mmol) in DMF (25 mL) was heated at 70° C. for 20 minutes. After cooling to ambient temperature, the reaction mixture was basified (11M NaOH) and brine was added. The resulting mixture was extracted with CHCl3 (×3). T... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCCN1.c1cnsn1 | c1cnsn1.C1C[NH]CCN1 | c1cnsn1.C1C[NH]CCN1 | null | [Cl-].[Na+].O.CN(C)C=O | 70 | null | C1CNCCN1.Clc1nsnc1Cl>[Cl-].[Na+].O.CN(C)C=O>Cl.Clc1nsnc1N1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ce211c22d47645f9b378ccf64f84926e | CC(C)(C)OC(=O)N1CCN(c2nccnc2Cl)CC1.OCCS>>CC(C)(C)OC(=O)N1CCN(c2nccnc2SCCO)CC1 | [OH-].[Na+].SCCO.ClC1=NC=CN=C1N1CCN(CC1)C(=O)OC(C)(C)C>>OCCSC=1C(=NC=CN1)N1CCN(CC1)C(=O)OC(C)(C)C | Cl[c:17]1[c:12]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:23][CH2:22]2)[n:13][cH:14][cH:15][n:16]1.[SH:18][CH2:19][CH2:20][OH:21]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[n:13][cH:14][cH:15][n:16][c:17]2[S:18][CH2:19][CH2:20][OH:21])[CH... | CC(C)(C)OC(=O)N1CCN(c2nccnc2Cl)CC1.OCCS | CC(C)(C)OC(=O)N1CCN(c2nccnc2SCCO)CC1 | null | null | O1CCOCC1.O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution thiol | ceff1a344f68f64f3ccbdc170e0e8518aee636d7d51efddd7ec4c746a215b670 | b7fe376f7aad2517725eef26ab981e4baa6c31c5f38fdf89e7c52a4a2c6cc1d2 | c1cnc(N2CCNCC2)cn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#7:7].[C:8]-[C:9]-[SH;D1;+0:10]>>[#7:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[S;H0;D2;+0:10]-[C:9]-[C:8] | 65.2 | [{"value": 65.0, "product": "OCCSC=1C(=NC=CN1)N1CCN(CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.2, "product": "OCCSC=1C(=NC=CN1)N1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | Sodium hydroxide (0.92 g, 23 mmol) was dissolved in water (9 mL) and dioxane (15 mL). 2-Mercaptoethanol (0.54 mL, 7.7 mmol) was added while stirring and 2-chloro-3-(4-tert-butoxycarbonyl-1-piperazinyl)pyrazine (2.3 g, 7.7 mmol, from Example 52, step 1) in dioxane (10 mL) was added. The reaction mixture was heated at 10... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aliphatic thiol | Monosulfide | c1cnccn1 | c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1 | HCl | O1CCOCC1.O | 100 | null | CC(C)(C)OC(=O)N1CCN(c2nccnc2Cl)CC1.OCCS>O1CCOCC1.O>CC(C)(C)OC(=O)N1CCN(c2nccnc2SCCO)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-51b277b3a8fa4880acb62b1176d21922 | CC(C)(C)OC(=O)N1CCNCC1.Clc1nsnc1Cl>>CC(C)(C)OC(=O)N1CCN(c2nsnc2Cl)CC1 | C(=O)(OC(C)(C)C)N1CCNCC1.C(=O)([O-])[O-].[K+].[K+].ClC1=NSN=C1Cl>>ClC=1C(=NSN1)N1CCN(CC1)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:18][CH2:19]1.Cl[c:12]1[n:13][s:14][n:15][c:16]1[Cl:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[n:13][s:14][n:15][c:16]2[Cl:17])[CH2:18][CH2:19]1 | CC(C)(C)OC(=O)N1CCNCC1.Clc1nsnc1Cl | CC(C)(C)OC(=O)N1CCN(c2nsnc2Cl)CC1 | null | null | O.CC#N.CCOC(=O)C | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 3991cfe8cc7ce136c577c51c08d126d93c8ef536de9d097cdf4a1fb2a87bf134 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1nsnc1N1CCNCC1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#16;a:3]:[#7;a:4]:[c:5]:1-[Cl;D1;H0:6].[#7:7]1-[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]-1>>[Cl;D1;H0:6]-[c:5]1:[#7;a:4]:[#16;a:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[N;H0;D3;+0:10]1-[C:11]-[C:12]-[#7:7]-[C:8]-[C:9]-1 | null | [] | 100 | CELSIUS | 4 | DAY | A mixture of N-Boc-piperazine (2.97 g, 15.9 mmol), K2CO3 (2.20 g, 15.9 mmol) and 3,4-dichloro-1,2,5-thiadiazole (1.5 mL, 15.9 mmol) in CH3CN (30 mL) was stirred at 100° C. for 19 h and at room temperature for 4 days. The reaction mixture was then diluted with EtOAc and water. The organic phase was dried (K2CO3) and the... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1C[NH]CCN1.c1cnsn1 | C1C[NH]CC[NH]1.c1cnsn1 | C1C[NH]CC[NH]1.c1cnsn1 | HCl | O.CC#N.CCOC(=O)C | 100 | 96 | CC(C)(C)OC(=O)N1CCNCC1.Clc1nsnc1Cl>O.CC#N.CCOC(=O)C>CC(C)(C)OC(=O)N1CCN(c2nsnc2Cl)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-401e75184394424a991e98a2894f3ddc | CC(C)(C)OC(=O)N1CCN(c2nsnc2Cl)CC1.OCCO>>CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCO)CC1 | ClC=1C(=NSN1)N1CCN(CC1)C(=O)OC(C)(C)C.C(CO)O>>OCCOC=1C(=NSN1)N1CCN(CC1)C(=O)OC(C)(C)C | Cl[c:16]1[c:12]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:22][CH2:21]2)[n:13][s:14][n:15]1.[OH:17][CH2:18][CH2:19][OH:20]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[n:13][s:14][n:15][c:16]2[O:17][CH2:18][CH2:19][OH:20])[CH2:21][CH2:22]1 | CC(C)(C)OC(=O)N1CCN(c2nsnc2Cl)CC1.OCCO | CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCO)CC1 | null | null | N1=CC=CC=C1.CCOC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 85f3a5bcedc3a3ca57fcccc5a225fd51bca5e111eec8d9d55c821c209d5319b1 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1nsnc1N1CCNCC1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[#16;a:3]:[#7;a:4]:[c:5]:1-[#7:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[#7:6]-[c:5]1:[#7;a:4]:[#16;a:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:9]-[C:8]-[C:7] | 79.6 | [{"value": 65.0, "product": "OCCOC=1C(=NSN1)N1CCN(CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.6, "product": "OCCOC=1C(=NSN1)N1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 8 | HOUR | K-t-BuO (1.24 g, 1 mmol) was added to a mixture of the product obtained in Step 1 (198 g, 6.5 mmol) and ethylene glycol (2.54 ml, 45.5 mmol) in pyridine (15 ml). The reaction mixture was stirred at 100° C. for 6 h and at room temperature overnight. The solution was then poured into ice-water and diluted with EtOAc. The... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cnsn1 | c1cnsn1 | C1C[NH]CC[NH]1.c1cnsn1 | HCl | N1=CC=CC=C1.CCOC(=O)C | 100 | 8 | CC(C)(C)OC(=O)N1CCN(c2nsnc2Cl)CC1.OCCO>N1=CC=CC=C1.CCOC(=O)C>CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCO)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-98b19d8ee6d64b53b83dce7acbe77625 | CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCO)CC1.O=c1ccc2ccc(O)cc2o1>>CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCOc2ccc3ccc(=O)oc3c2)CC1 | OCCOC=1C(=NSN1)N1CCN(CC1)C(=O)OC(C)(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.OC1=CC=C2C=CC(OC2=C1)=O.N(=NC(=O)OCC)C(=O)OCC>>O=C1OC2=CC(=CC=C2C=C1)OCCOC=1C(=NSN1)N1CCN(CC1)C(=O)OC(C)(C)C | O[CH2:19][CH2:18][O:17][c:16]1[c:12]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:33][CH2:32]2)[n:13][s:14][n:15]1.[OH:20][c:21]1[cH:22][cH:23][c:24]2[cH:25][cH:26][c:27](=[O:28])[o:29][c:30]2[cH:31]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12... | CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCO)CC1.O=c1ccc2ccc(O)cc2o1 | CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCOc2ccc3ccc(=O)oc3c2)CC1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | O=c1ccc2ccc(OCCOc3nsnc3N3CCNCC3)cc2o1 | O-[CH2;D2;+0:1]-[C:2]-[#8:3].[#8;a:4]:[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]:[c:5]:[#8;a:4] | 123.6 | [{"value": 123.6, "product": "O=C1OC2=CC(=CC=C2C=C1)OCCOC=1C(=NSN1)N1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | DAY | Diethyl azodicarboxylate (DEAD, 61 μl, 0.39 mmol) was added drop wise to a mixture of the product obtained in Step 2 (100 mg, 0.30 mmol), triphenylphosphine (102 mg, 0.39 mmol) and 7-hydroxycoumarin (63 mg, 0.39 mmol) in dry THF (5 mL). The reaction mixture was stirred at room temperature for 5 days. After solvent remo... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | C1C[NH]CC[NH]1.c1cnsn1.c1ccc2cccoc2c1 | HO- | C1CCOC1 | null | 120 | CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCO)CC1.O=c1ccc2ccc(O)cc2o1>C1CCOC1>CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCOc2ccc3ccc(=O)oc3c2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8e8efdfb6a344bea937cd950ad54cd50 | CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCOc2ccc3ccc(=O)oc3c2)CC1>>O=c1ccc2ccc(OCCOc3nsnc3N3CCNCC3)cc2o1 | O=C1OC2=CC(=CC=C2C=C1)OCCOC=1C(=NSN1)N1CCN(CC1)C(=O)OC(C)(C)C.FC(C(=O)O)(F)F>>N1(CCNCC1)C=1C(=NSN1)OCCOC1=CC=C2C=CC(OC2=C1)=O | CC(C)(C)OC(=O)[N:21]1[CH2:20][CH2:19][N:18]([c:17]2[c:13]([O:12][CH2:11][CH2:10][O:9][c:8]3[cH:7][cH:6][c:5]4[cH:4][cH:3][c:2](=[O:1])[o:26][c:25]4[cH:24]3)[n:14][s:15][n:16]2)[CH2:23][CH2:22]1>>[O:1]=[c:2]1[cH:3][cH:4][c:5]2[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][O:12][c:13]3[n:14][s:15][n:16][c:17]3[N:18]3[CH2:19][CH... | CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCOc2ccc3ccc(=O)oc3c2)CC1 | O=c1ccc2ccc(OCCOc3nsnc3N3CCNCC3)cc2o1 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=c1ccc2ccc(OCCOc3nsnc3N3CCNCC3)cc2o1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | null | [] | 0 | CELSIUS | 1 | HOUR | The product obtained in Step 3 (176 mg) was diluted in CH2Cl2 (1.5 mL) and cooled to ˜0° C. Trifluoroacetic acid (0.5 mL) was added and the reaction mixture was stirred for 1 h at 5° C. After solvent removal in vacuo, the residue was purified by chromatography on silica gel using hexane/EtOAc (1:1) followed by CH2Cl2/M... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccc2cccoc2c1.c1cnsn1.C1C[NH]CCN1 | HO- | C(Cl)Cl | 0 | 1 | CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCOc2ccc3ccc(=O)oc3c2)CC1>C(Cl)Cl>O=c1ccc2ccc(OCCOc3nsnc3N3CCNCC3)cc2o1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b5614b95bb174987a2df04178fb2173e | CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCO)CC1.Oc1ccc2ccncc2c1>>CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCOc2ccc3ccncc3c2)CC1 | OC1=CC=C2C=CN=CC2=C1.OCCOC=1C(=NSN1)N1CCN(CC1)C(=O)OC(C)(C)C.N(=NC(=O)OCC)C(=O)OCC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C1=NC=CC2=CC=C(C=C12)OCCOC=1C(=NSN1)N1CCN(CC1)C(=O)OC(C)(C)C | O[CH2:19][CH2:18][O:17][c:16]1[c:12]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:32][CH2:31]2)[n:13][s:14][n:15]1.[OH:20][c:21]1[cH:22][cH:23][c:24]2[cH:25][cH:26][n:27][cH:28][c:29]2[cH:30]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[n:13]... | CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCO)CC1.Oc1ccc2ccncc2c1 | CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCOc2ccc3ccncc3c2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1cc2ccc(OCCOc3nsnc3N3CCNCC3)cc2cn1 | O-[CH2;D2;+0:1]-[C:2]-[#8:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 5 | DAY | The title compound was prepared according to the procedure of Example 218, Step 3 starting from the product of Example 218, Step 2 (100 mg, 0.30 mmol), triphenylphosphine (102 mg, 0.39 mmol), 7-hydroxyisoquinoline (57 mg, 0.39 mmol) and diethyl azodicarboxylate (61 μl, 0.39 mmol) except that the reaction mixture was st... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | C1C[NH]CC[NH]1.c1cnsn1.c1ccc2cnccc2c1 | HO- | null | null | 120 | CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCO)CC1.Oc1ccc2ccncc2c1>>CC(C)(C)OC(=O)N1CCN(c2nsnc2OCCOc2ccc3ccncc3c2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cc362952def14ec9ad18caceddb44035 | CC(C)(C)OC(=O)N1CCN(c2nccnc2Cl)CC1.OCCOc1cccc(O)c1>>CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCOc2cccc(O)c2)CC1 | ClC1=NC=CN=C1N1CCN(CC1)C(=O)OC(C)(C)C.OC=1C=C(OCCO)C=CC1.[H-].[Na+]>>OC=1C=C(OCCOC=2C(=NC=CN2)N2CCN(CC2)C(=O)OC(C)(C)C)C=CC1 | Cl[c:17]1[c:12]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:30][CH2:29]2)[n:13][cH:14][cH:15][n:16]1.[OH:18][CH2:19][CH2:20][O:21][c:22]1[cH:23][cH:24][cH:25][c:26]([OH:27])[cH:28]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][N:11]([c:12]2[n:13][cH:14][cH... | CC(C)(C)OC(=O)N1CCN(c2nccnc2Cl)CC1.OCCOc1cccc(O)c1 | CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCOc2cccc(O)c2)CC1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8088ac3623a2ee47f375f73ca665bec9cf80b1384463e6e2f03125aecbcea517 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(OCCOc2nccnc2N2CCNCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#7:7].[C:8]-[C:9]-[OH;D1;+0:10]>>[#7:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:10]-[C:9]-[C:8] | 94 | [{"value": 94.0, "product": "OC=1C=C(OCCOC=2C(=NC=CN2)N2CCN(CC2)C(=O)OC(C)(C)C)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | 1.75 | HOUR | To a stirred solution of 2-(3-hydroxyphenoxy)ethanol (7.71 g, 0.05 mol) in dry DMF to (100 mL) at ˜0° C. (ice bath) was added NaH (3.90 g, 0.163 mol) in portions under N2. When the H2-evolution had ceased, a solution of 2-chloro-3-(4-tert-butoxycarbonyl-1-piperazinyl)pyrazine (0.05 mol, 14.9 g; from Example 52, Step 1)... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cnccn1 | c1cnccn1 | C1C[NH]CC[NH]1.c1cnccn1.c1ccccc1 | HCl | CN(C)C=O | 65 | 1.75 | CC(C)(C)OC(=O)N1CCN(c2nccnc2Cl)CC1.OCCOc1cccc(O)c1>CN(C)C=O>CC(C)(C)OC(=O)N1CCN(c2nccnc2OCCOc2cccc(O)c2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-87f51bec0164419d94ede3554fb73ac6 | COCCOc1cccc(OCCOc2nccnc2N2CCN(C(=O)OC(C)(C)C)CC2)c1>>COCCOc1cccc(OCCOc2nccnc2N2CCNCC2)c1 | COCCOC=1C=C(OCCOC=2C(=NC=CN2)N2CCN(CC2)C(=O)OC(C)(C)C)C=CC1>>COCCOC=1C=C(OCCOC2=NC=CN=C2N2CCNCC2)C=CC1 | CC(C)(C)OC(=O)[N:24]1[CH2:23][CH2:22][N:21]([c:20]2[c:15]([O:14][CH2:13][CH2:12][O:11][c:10]3[cH:9][cH:8][cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:27]3)[n:16][cH:17][cH:18][n:19]2)[CH2:26][CH2:25]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][O:14][c:15]2[n:16][cH:17][cH:1... | COCCOc1cccc(OCCOc2nccnc2N2CCN(C(=O)OC(C)(C)C)CC2)c1 | COCCOc1cccc(OCCOc2nccnc2N2CCNCC2)c1 | null | null | Cl.CCOCC.CCOCC.CCOC(=O)C | Reduction | Boc amine deprotection | 2c25e19aee181a3c5131cfdfda27035fd54d4379a11d745dfb75d386bacfd500 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(OCCOc2nccnc2N2CCNCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:6]-[C:5]-1 | 69 | [{"value": 69.0, "product": "COCCOC=1C=C(OCCOC2=NC=CN=C2N2CCNCC2)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | The product obtained in Step 1 above was dissolved in a mixture of EtOAc (18 mL) and ether (9 mL) and 5 M HCl/ether (9 mL) was added. The mixture was stirred at room temperature for 3 h. The precipitated hydrochloride salt was filtered off and washed thoroughly with ether. The hydrochloride was dissolved in EtOAc/MeOH/... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1C[NH]CC[NH]1 | C1C[NH]CCN1 | c1ccccc1.c1cnccn1.C1C[NH]CCN1 | HO- | Cl.CCOCC.CCOCC.CCOC(=O)C | null | 3 | COCCOc1cccc(OCCOc2nccnc2N2CCN(C(=O)OC(C)(C)C)CC2)c1>Cl.CCOCC.CCOCC.CCOC(=O)C>COCCOc1cccc(OCCOc2nccnc2N2CCNCC2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0459f422d40948fabce3b5626e5172db | COc1ccc(CO)cc1.Clc1nccnc1N1CCNCC1>>COc1ccc(COc2nccnc2N2CCNCC2)cc1 | ClC1=NC=CN=C1N1CCNCC1.COC1=CC=C(CO)C=C1>>COC1=CC=C(COC2=NC=CN=C2N2CCNCC2)C=C1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[cH:21][cH:22]1.Cl[c:9]1[n:10][cH:11][cH:12][n:13][c:14]1[N:15]1[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][c:9]2[n:10][cH:11][cH:12][n:13][c:14]2[N:15]2[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]2)[cH:21][cH:22]1 | COc1ccc(CO)cc1.Clc1nccnc1N1CCNCC1 | COc1ccc(COc2nccnc2N2CCNCC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8088ac3623a2ee47f375f73ca665bec9cf80b1384463e6e2f03125aecbcea517 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(COc2nccnc2N2CCNCC2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[#7:7].[OH;D1;+0:8]-[C:9]-[c:10]>>[#7:7]-[c:6]1:[#7;a:5]:[c:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:8]-[C:9]-[c:10] | 72 | [{"value": 72.0, "product": "COC1=CC=C(COC2=NC=CN=C2N2CCNCC2)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The title compound was prepared according to the procedure of Example 90, Step 2, starting from 2-chloro-3-(1-piperazinyl)pyrazine (0.80 g, 4.0 mmol; from Example 90, Step 1) and 4-methoxybenzyl alcohol (0.88 g, 6.4 mmol). Oil; yield 72%. MS m/z 301 (M+H)+.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1cnccn1 | c1cnccn1 | c1ccccc1.c1cnccn1.C1C[NH]CCN1 | HCl | null | null | null | COc1ccc(CO)cc1.Clc1nccnc1N1CCNCC1>>COc1ccc(COc2nccnc2N2CCNCC2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fe6be616f9574daeb2b80cc5ee418c40 | Clc1cc(Cl)nc(Cl)n1.FC(F)c1nc2ccccc2[nH]1>>FC(F)c1nc2ccccc2n1-c1nc(Cl)cc(Cl)n1 | O.[H-].[Na+].FC(C=1NC2=C(N1)C=CC=C2)F.ClC1=NC(=CC(=N1)Cl)Cl>>ClC1=NC(=NC(=C1)Cl)N1C(=NC2=C1C=CC=C2)C(F)F | Cl[c:13]1[n:14][c:15]([Cl:16])[cH:17][c:18]([Cl:19])[n:20]1.[F:1][CH:2]([F:3])[c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[nH:12]1>>[F:1][CH:2]([F:3])[c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1-[c:13]1[n:14][c:15]([Cl:16])[cH:17][c:18]([Cl:19])[n:20]1 | Clc1cc(Cl)nc(Cl)n1.FC(F)c1nc2ccccc2[nH]1 | FC(F)c1nc2ccccc2n1-c1nc(Cl)cc(Cl)n1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 4298ad87b3fff687c9179de37beeb6526c6797b156d79bab2f6a2c088e12b01a | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1cnc(-n2cnc3ccccc32)nc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[c:7]1:[#7;a:8]:[c:9](:[c:10]):[c:11](:[c:12]):[nH;D2;+0:13]:1>>[C:6]-[c:7]1:[#7;a:8]:[c:9](:[c:10]):[c:11](:[c:12]):[n;H0;D3;+0:13]:1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | 62.2 | [{"value": 62.0, "product": "ClC1=NC(=NC(=C1)Cl)N1C(=NC2=C1C=CC=C2)C(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.2, "product": "ClC1=NC(=NC(=C1)Cl)N1C(=NC2=C1C=CC=C2)C(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | 0.84 g (5 mmol) of 2-difluoromethylbenzimidazole dissolved in DMF (25 ml) was added and reacted with 60% sodium hydride (0.24 g, 6 mmol) at room temperature for 30 minutes. This suspension was added to a solution of 2,4,6-trichloropyrimidine (0.92 g, 5 mmol) dissolved in DMF (25 ml) and stirred at room temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1cncnc1.c1ccc2[nH]cnc2c1 | c1nc2ccccc2[nH]1.c1cncnc1 | c1nc2ccccc2[nH]1.c1cncnc1 | HCl | CN(C)C=O | null | 1.5 | Clc1cc(Cl)nc(Cl)n1.FC(F)c1nc2ccccc2[nH]1>CN(C)C=O>FC(F)c1nc2ccccc2n1-c1nc(Cl)cc(Cl)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1024bf11d77148c69155ab9d4a3af94c | C1COCCN1.C[C@@H]1OCCN(c2cc(Cl)nc(-n3c(C(F)F)nc4ccccc43)n2)[C@@H]1C>>C[C@@H]1OCCN(c2cc(N3CCOCC3)nc(-n3c(C(F)F)nc4ccccc43)n2)[C@@H]1C | ClC1=NC(=NC(=C1)N1[C@@H]([C@@H](OCC1)C)C)N1C(=NC2=C1C=CC=C2)C(F)F.N1CCOCC1>>FC(C1=NC2=C(N1C1=NC(=CC(=N1)N1[C@@H]([C@@H](OCC1)C)C)N1CCOCC1)C=CC=C2)F | [NH:10]1[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1.Cl[c:9]1[cH:8][c:7]([N:6]2[CH2:5][CH2:4][O:3][C@@H:2]([CH3:1])[C@H:31]2[CH3:32])[n:30][c:17](-[n:18]2[c:19]([CH:20]([F:21])[F:22])[n:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]23)[n:16]1>>[CH3:1][C@@H:2]1[O:3][CH2:4][CH2:5][N:6]([c:7]2[cH:8][c:9]([N:10]3[CH2:11][CH2:12][... | C1COCCN1.C[C@@H]1OCCN(c2cc(Cl)nc(-n3c(C(F)F)nc4ccccc43)n2)[C@@H]1C | C[C@@H]1OCCN(c2cc(N3CCOCC3)nc(-n3c(C(F)F)nc4ccccc43)n2)[C@@H]1C | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | b6ba2533a469a91b7ece94b4a523fa9d9d9bc584236787b5a2be96cdf7a917fc | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2c(c1)ncn2-c1nc(N2CCOCC2)cc(N2CCOCC2)n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7;a:4]):[#7;a:5]:[c:6](-[#7:7]):[c:8]:1.[#8:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#7:7]-[c:6]1:[#7;a:5]:[c:3](-[#7;a:4]):[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:11]-[C:10]-[#8:9]-[C:14]-[C:13]-2):[c:8]:1 | 91.7 | [{"value": 90.0, "product": "FC(C1=NC2=C(N1C1=NC(=CC(=N1)N1[C@@H]([C@@H](OCC1)C)C)N1CCOCC1)C=CC=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.7, "product": "FC(C1=NC2=C(N1C1=NC(=CC(=N1)N1[C@@H]([C@@H](OCC1)C)C)N1CCOCC1)C=CC=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 1 | HOUR | 0.84 g (5 mmol) of 2-difluoromethylbenzimidazole dissolved in DMF (25 ml) was added and reacted with 60% sodium hydride (0.24 g, 6 mmol) at room temperature for 30 minutes. This suspension was added to a solution of 2,4,6-trichloropyrimidine (0.92 g, 5 mmol) dissolved in DMF (25 ml) and stirred at room temperature for ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1cncnc1 | c1cncnc1.C1COCC[NH]1 | C1COCC[NH]1.c1cncnc1.C1COCC[NH]1.c1nc2ccccc2[nH]1 | HCl | null | 70 | 1 | C1COCCN1.C[C@@H]1OCCN(c2cc(Cl)nc(-n3c(C(F)F)nc4ccccc43)n2)[C@@H]1C>>C[C@@H]1OCCN(c2cc(N3CCOCC3)nc(-n3c(C(F)F)nc4ccccc43)n2)[C@@H]1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-41380e62366441e898e069d6f8e656f9 | Clc1nc(Cl)nc(N2CCOCC2)n1.FC(F)c1nc2ccccc2[nH]1>>FC(F)c1nc2ccccc2n1-c1nc(Cl)nc(N2CCOCC2)n1 | ClC1=NC(=NC(=N1)Cl)N1CCOCC1.FC(C=1NC2=C(N1)C=CC=C2)F.C([O-])([O-])=O.[K+].[K+].CN(C)C=O>>ClC1=NC(=NC(=N1)N1CCOCC1)N1C(=NC2=C1C=CC=C2)C(F)F | Cl[c:13]1[n:14][c:15]([Cl:16])[n:17][c:18]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[n:25]1.[F:1][CH:2]([F:3])[c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[nH:12]1>>[F:1][CH:2]([F:3])[c:4]1[n:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[n:12]1-[c:13]1[n:14][c:15]([Cl:16])[n:17][c:18]([N:19]2[CH2:20][CH2:21][O:22]... | Clc1nc(Cl)nc(N2CCOCC2)n1.FC(F)c1nc2ccccc2[nH]1 | FC(F)c1nc2ccccc2n1-c1nc(Cl)nc(N2CCOCC2)n1 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | de8ca90b6a87d8cb2c34d2d3043201922cff5cf5653513773b5948279865a7ce | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2c(c1)ncn2-c1ncnc(N2CCOCC2)n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[#7;a:7]:1.[C:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[nH;D2;+0:15]:1>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[n;H0;D3;+0:15]2:[c:13](:[c:14]):[c:11](:[c:12]):[#7;a:10]:[c:9]:2-[C:8]):[#7;a:7]:1 | 86 | [{"value": 86.0, "product": "ClC1=NC(=NC(=N1)N1CCOCC1)N1C(=NC2=C1C=CC=C2)C(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.6, "product": "ClC1=NC(=NC(=N1)N1CCOCC1)N1C(=NC2=C1C=CC=C2)C(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 11.8 g (50 mmol) of 2,4-dichloro-6-morpholino-1,3,5-triazine, 8.41 g (50 mmol) of 2-difluoromethyl-benzimidazole and 55.3 g (400 mmol) of anhydrous potassium carbonate added to DMF (250 ml) were stirred at room temperature for 16 hours. The reaction solution was poured into water and the resulting precipitates were was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ncncn1.c1ccc2[nH]cnc2c1 | c1nc2ccccc2[nH]1.c1ncncn1 | c1nc2ccccc2[nH]1.c1ncncn1.C1COCC[NH]1 | HCl | O | null | 16 | Clc1nc(Cl)nc(N2CCOCC2)n1.FC(F)c1nc2ccccc2[nH]1>O>FC(F)c1nc2ccccc2n1-c1nc(Cl)nc(N2CCOCC2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ce4b2890a50f4b1cb2d14522ba431039 | C[C@@H]1NCCO[C@@H]1C.FC(F)c1nc2ccccc2n1-c1nc(Cl)nc(N2CCOCC2)n1>>C[C@@H]1OCCN(c2nc(N3CCOCC3)nc(-n3c(C(F)F)nc4ccccc43)n2)[C@@H]1C | ClC1=NC(=NC(=N1)N1CCOCC1)N1C(=NC2=C1C=CC=C2)C(F)F.Cl.C[C@@H]1[C@@H](NCCO1)C.C([O-])([O-])=O.[K+].[K+].CN(C)C=O>>FC(C1=NC2=C(N1C1=NC(=NC(=N1)N1[C@@H]([C@@H](OCC1)C)C)N1CCOCC1)C=CC=C2)F | [CH3:1][C@H:2]1[O:3][CH2:4][CH2:5][NH:6][C@H:31]1[CH3:32].Cl[c:7]1[n:8][c:9]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[n:16][c:17](-[n:18]2[c:19]([CH:20]([F:21])[F:22])[n:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]23)[n:30]1>>[CH3:1][C@@H:2]1[O:3][CH2:4][CH2:5][N:6]([c:7]2[n:8][c:9]([N:10]3[CH2:11][CH2:12][O:13]... | C[C@@H]1NCCO[C@@H]1C.FC(F)c1nc2ccccc2n1-c1nc(Cl)nc(N2CCOCC2)n1 | C[C@@H]1OCCN(c2nc(N3CCOCC3)nc(-n3c(C(F)F)nc4ccccc43)n2)[C@@H]1C | null | null | O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 93a150f14ca1246791130f1830975e6ad6685a37209989974b5c61095e16cfc0 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc2c(c1)ncn2-c1nc(N2CCOCC2)nc(N2CCOCC2)n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#7;a:4]):[#7;a:5]:[c:6]:[#7;a:7]:1.[C;D1;H3:8]-[C:9]1-[C:10]-[#8:11]-[C:12]-[C:13]-[NH;D2;+0:14]-1>>[#7;a:4]-[c:3]1:[#7;a:5]:[c:6]:[#7;a:7]:[c;H0;D3;+0:1](-[N;H0;D3;+0:14]2-[C:13]-[C:12]-[#8:11]-[C:10]-[C:9]-2-[C;D1;H3:8]):[#7;a:2]:1 | 87 | [{"value": 87.0, "product": "FC(C1=NC2=C(N1C1=NC(=NC(=N1)N1[C@@H]([C@@H](OCC1)C)C)N1CCOCC1)C=CC=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.0, "product": "FC(C1=NC2=C(N1C1=NC(=NC(=N1)N1[C@@H]([C@@H](OCC1)C)C)N1CCOCC1)C=CC=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 11.8 g (50 mmol) of 2,4-dichloro-6-morpholino-1,3,5-triazine, 8.41 g (50 mmol) of 2-difluoromethyl-benzimidazole and 55.3 g (400 mmol) of anhydrous potassium carbonate added to DMF (250 ml) were stirred at room temperature for 16 hours. The reaction solution was poured into water and the resulting precipitates were was... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ncncn1 | C1COCC[NH]1.c1ncncn1 | C1COCC[NH]1.c1ncncn1.C1COCC[NH]1.c1nc2ccccc2[nH]1 | HCl | O | null | 16 | C[C@@H]1NCCO[C@@H]1C.FC(F)c1nc2ccccc2n1-c1nc(Cl)nc(N2CCOCC2)n1>O>C[C@@H]1OCCN(c2nc(N3CCOCC3)nc(-n3c(C(F)F)nc4ccccc43)n2)[C@@H]1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-973a0255d7144497b4821cb1ab64dd54 | FC(F)c1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCSCC2)n1>>O=S1CCN(c2nc(N3CCOCC3)nc(-n3c(C(F)F)nc4ccccc43)n2)CC1 | FC(C1=NC2=C(N1C1=NC(=NC(=N1)N1CCOCC1)N1CCSCC1)C=CC=C2)F.ClC1=CC(=CC=C1)C(=O)OO.O>>FC(C1=NC2=C(N1C1=NC(=NC(=N1)N1CCOCC1)N1CCS(CC1)=O)C=CC=C2)F | [S:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][c:8]([N:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)[n:15][c:16](-[n:17]3[c:18]([CH:19]([F:20])[F:21])[n:22][c:23]4[cH:24][cH:25][cH:26][cH:27][c:28]34)[n:29]2)[CH2:30][CH2:31]1>>[O:1]=[S:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][c:8]([N:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)[n:15][c:... | FC(F)c1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCSCC2)n1 | O=S1CCN(c2nc(N3CCOCC3)nc(-n3c(C(F)F)nc4ccccc43)n2)CC1 | null | null | ClCCl | Oxidation | Sulfanyl to sulfinyl | c85a23881a8c3a3231ed34b602ece3d962b8a98fadea32e6ade07ff31a14194b | f5f6bb6ca76a2267cd589767b4d67e7a17ab1ac383eeb6143dcd5d92e00e1b6a | O=S1CCN(c2nc(N3CCOCC3)nc(-n3cnc4ccccc43)n2)CC1 | [#7:1]1-[C:2]-[C:3]-[S;H0;D2;+0:4]-[C:5]-[C:6]-1>>[O;D1;H0:7]=[S;H0;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | 42.9 | [{"value": 42.0, "product": "FC(C1=NC2=C(N1C1=NC(=NC(=N1)N1CCOCC1)N1CCS(CC1)=O)C=CC=C2)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 42.9, "product": "FC(C1=NC2=C(N1C1=NC(=NC(=N1)N1CCOCC1)N1CCS(CC1)=O)C=CC=C2)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | 0.61 g (1.4 mmol) of 2-(2-difluoromethylbenzimidazol-1-yl)-4-morpholino-6-thiomorpholino-1,3,5-triazine dissolved in dichloromethane (20 ml) was added with m-chloroperbenzoic acid (0.35 g, 2.0 mmol) and stirred at room temperature for 16 hours. The reaction solution was poured into water and extracted with ethyl acetat... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfoxide | C1CSCC[NH]1 | C1CSCC[NH]1 | C1CSCC[NH]1.c1ncncn1.C1COCC[NH]1.c1nc2ccccc2[nH]1 | null | ClCCl | null | 16 | FC(F)c1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCSCC2)n1>ClCCl>O=S1CCN(c2nc(N3CCOCC3)nc(-n3c(C(F)F)nc4ccccc43)n2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ea4fa84f58b14006b5a9e9d83c326429 | Clc1nc(N2CCOCC2)nc(N2CCOCC2)n1.Nc1nc2ccccc2[nH]1>>Nc1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCOCC2)n1 | O.[H-].[Na+].NC=1NC2=C(N1)C=CC=C2.ClC1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1>>NC1=NC2=C(N1C1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1)C=CC=C2 | Cl[c:11]1[n:12][c:13]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[n:20][c:21]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[n:28]1.[NH2:1][c:2]1[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[nH:10]1>>[NH2:1][c:2]1[n:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[n:10]1-[c:11]1[n:12][c:13]([N:14]2[CH2:15][CH2:16][O:17][CH2:18]... | Clc1nc(N2CCOCC2)nc(N2CCOCC2)n1.Nc1nc2ccccc2[nH]1 | Nc1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCOCC2)n1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | de8ca90b6a87d8cb2c34d2d3043201922cff5cf5653513773b5948279865a7ce | e3660767655c50df0f92afc78c794dd2af7cf646bf1430960eafd30c23bf3fa7 | c1ccc2c(c1)ncn2-c1nc(N2CCOCC2)nc(N2CCOCC2)n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](-[#7:6]):[#7;a:7]:1.[N;D1;H2:8]-[c:9]1:[#7;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[nH;D2;+0:15]:1>>[#7:6]-[c:5]1:[#7;a:4]:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[n;H0;D3;+0:15]2:[c:9](-[N;D1;H2:8]):[#7;a:10]:[c:11](:[c:12]):[c:13]:2:[c:14]):[#7;a:7]:1 | 93 | [{"value": 93.0, "product": "NC1=NC2=C(N1C1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.6, "product": "NC1=NC2=C(N1C1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 9.32 g (70 mmol) of 2-aminobenzimidazole dissolved in DMF (300 ml) was added and reacted with 60% sodium hydride (2.80 g, 70 mmol) at room temperature for 30 minutes. This suspension was added to a solution of 14.3 g (50 mmol) of 2-chloro-4,6-dimorpholino-1,3,5-triazine dissolved in DMF (200 ml) and stirred at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ncncn1.c1ccc2[nH]cnc2c1 | c1nc2ccccc2[nH]1.c1ncncn1 | c1nc2ccccc2[nH]1.c1ncncn1.C1COCC[NH]1.C1COCC[NH]1 | HCl | CN(C)C=O | null | 2 | Clc1nc(N2CCOCC2)nc(N2CCOCC2)n1.Nc1nc2ccccc2[nH]1>CN(C)C=O>Nc1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCOCC2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8d5cb1d72fbf4e4bb26686f07a0a19c8 | CC(=O)O.Nc1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCOCC2)n1>>CC(=O)Nc1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCOCC2)n1 | C(Cl)(Cl)Cl.NC1=NC2=C(N1C1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1)C=CC=C2.C(C)(=O)O.C1CCC(CC1)N=C=NC2CCCCC2>>C(C)(=O)NC1=NC2=C(N1C1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1)C=CC=C2 | O[C:2]([CH3:1])=[O:3].[NH2:4][c:5]1[n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[n:13]1-[c:14]1[n:15][c:16]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[n:23][c:24]([N:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)[n:31]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[n:6][c:7]2[cH:8][cH:9][cH:10][cH:11][c:12]2[n:13]1-[c:14]1[n:15]... | CC(=O)O.Nc1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCOCC2)n1 | CC(=O)Nc1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCOCC2)n1 | null | null | O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc2c(c1)ncn2-c1nc(N2CCOCC2)nc(N2CCOCC2)n1 | O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[#7;a:4]:[c:5](-[#7;a:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]:1-[NH2;D1;+0:11]):[#7;a:12]>>[#7;a:4]:[c:5](-[#7;a:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]:1-[NH;D2;+0:11]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]):[#7;a:12] | 73 | [{"value": 73.0, "product": "C(C)(=O)NC1=NC2=C(N1C1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.0, "product": "C(C)(=O)NC1=NC2=C(N1C1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | 9.32 g (70 mmol) of 2-aminobenzimidazole dissolved in DMF (300 ml) was added and reacted with 60% sodium hydride (2.80 g, 70 mmol) at room temperature for 30 minutes. This suspension was added to a solution of 14.3 g (50 mmol) of 2-chloro-4,6-dimorpholino-1,3,5-triazine dissolved in DMF (200 ml) and stirred at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1nc2ccccc2[nH]1.c1ncncn1.C1COCC[NH]1.C1COCC[NH]1 | HO- | O | null | 4 | CC(=O)O.Nc1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCOCC2)n1>O>CC(=O)Nc1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCOCC2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eac1321f2c99465f8fa75f66bfd88b15 | Nc1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCOCC2)n1.O=COCCl>>COC(=O)Nc1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCOCC2)n1 | CN(C)C=O.NC1=NC2=C(N1C1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1)C=CC=C2.[H-].[Na+].ClCOC=O>>COC(=O)NC1=NC2=C(N1C1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1)C=CC=C2 | [NH2:5][c:6]1[n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[n:14]1-[c:15]1[n:16][c:17]([N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[n:24][c:25]([N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)[n:32]1.Cl[CH2:1][O:2][CH:3]=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[n:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[n:14]1-[... | Nc1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCOCC2)n1.O=COCCl | COC(=O)Nc1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCOCC2)n1 | null | null | O | Protection | OtherReaction | 818a2638852ca067e1660d3f7cba4ccd667da7676c6594aef25d50435f6412db | d511adec1b387885496ae9a429ba76ae4c5fd3f4cd4823260b0f617a8bf4476d | c1ccc2c(c1)ncn2-c1nc(N2CCOCC2)nc(N2CCOCC2)n1 | Cl-[CH2;D2;+0:1]-[#8:2]-[CH;D2;+0:3]=[O;D1;H0:4].[#7;a:5]:[c:6](-[#7;a:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:1-[NH2;D1;+0:12]):[#7;a:13]>>[#7;a:5]:[c:6](-[#7;a:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:1-[NH;D2;+0:12]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#8:2]-[CH3;D1;+0:1]):[#7;a:13] | 46 | [{"value": 46.0, "product": "COC(=O)NC1=NC2=C(N1C1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.4, "product": "COC(=O)NC1=NC2=C(N1C1=NC(=NC(=N1)N1CCOCC1)N1CCOCC1)C=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.19 g (0.50 mmol) of 2-(2-aminobenzimidazol-1-yl)-4,6-dimorpholino-1,3,5-triazine synthesized in (1) of the Example 6 and 60% sodium hydride (24 mg, 0.60 mmol) added to DMF (2 ml) were reacted at room temperature for 1 hour. The reaction mixture was added and reacted with 0.040 ml (0.55 mmol) of chloromethylformate at... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Primary amine | Carbamic ester.Ether | null | null | c1nc2ccccc2[nH]1.c1ncncn1.C1COCC[NH]1.C1COCC[NH]1 | HCl | O | null | null | Nc1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCOCC2)n1.O=COCCl>O>COC(=O)Nc1nc2ccccc2n1-c1nc(N2CCOCC2)nc(N2CCOCC2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ded3e55de6ba4c58b7ab83aa957d0d54 | O=[N+]([O-])c1ccc2c(c1)nc(C(F)F)n2-c1nc(N2CCOCC2)cc(N2CCOCC2)n1.O=[N+]([O-])c1ccc2nc(C(F)F)n(-c3nc(N4CCOCC4)cc(N4CCOCC4)n3)c2c1>>Nc1ccc2nc(C(F)F)n(-c3nc(N4CCOCC4)cc(N4CCOCC4)n3)c2c1 | FC(C=1NC2=C(N1)C=CC=C2)F.FC(C1=NC2=C(N1C1=NC(=CC(=N1)N1CCOCC1)N1CCOCC1)C=CC(=C2)[N+](=O)[O-])F.FC(C1=NC2=C(N1C1=NC(=CC(=N1)N1CCOCC1)N1CCOCC1)C=C(C=C2)[N+](=O)[O-])F>>NC=1C=CC2=C(N(C(=N2)C(F)F)C2=NC(=CC(=N2)N2CCOCC2)N2CCOCC2)C1 | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]2[n:6](-c3nc(N4CCOCC4)cc(N4CCOCC4)n3)[c:7]([CH:8]([F:9])[F:10])[n:11][c:30]2[cH:31]1.O=[N+]([O-])c1ccc2nc(C(F)F)n(-[c:12]3[n:13][c:14]([N:15]4[CH2:16][CH2:17][O:18][CH2:19][CH2:20]4)[cH:21][c:22]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)[n:29]3)c2c1>>[NH2:1][c:2]1[cH:3][cH:4][... | O=[N+]([O-])c1ccc2c(c1)nc(C(F)F)n2-c1nc(N2CCOCC2)cc(N2CCOCC2)n1.O=[N+]([O-])c1ccc2nc(C(F)F)n(-c3nc(N4CCOCC4)cc(N4CCOCC4)n3)c2c1 | Nc1ccc2nc(C(F)F)n(-c3nc(N4CCOCC4)cc(N4CCOCC4)n3)c2c1 | null | null | null | Functional Group Interconversion | OtherReaction | 4792b62a0e5fb6412b5601e7af951cb5e624b3e84008e1c31e06298263fdca44 | 4c2e6555ce5dfeed8f764b785e50f9149644539fa987a33281a90ed9b866b296 | c1ccc2c(c1)ncn2-c1nc(N2CCOCC2)cc(N2CCOCC2)n1 | F-C(-F)-c1:n:c2:c:c:c(-[N+](=O)-[O-]):c:c:2:n:1-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].O=[N+;H0;D3:6](-[O-])-[c:7]1:[c:8]:[c:9]2:[n;H0;D2;+0:10]:[c:11](-[C:12]):[n;H0;D3;+0:13](-c3:n:c(-N4-C-C-O-C-C-4):c:c(-N4-C-C-O-C-C-4):n:3):[c:14]:2:[c:15]:[c:16]:1>>[C:12]-[c:11]1:[n;H0;D2;+0:13]:[c:14]2:[c:15]:[c:16]:[c:7]... | 88 | [{"value": 88.0, "product": "NC=1C=CC2=C(N(C(=N2)C(F)F)C2=NC(=CC(=N2)N2CCOCC2)N2CCOCC2)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In accordance with the procedure of the Example 1 except that 2-difluoromethylbenzimidazole in (1) of the Example 1 was replaced by 2-difluoro-6-nitrobenzimidazole, a mixture of 2-(2-difluoromethyl-5-nitrobenzimidazol-1-yl)-4,6-dimorpholinopyrimidine with 2-(2-difluoromethyl-6-nitrobenzimidazol-1-yl)-4,6-dimorpholinopy... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Ether.Ether.Nitro group.Nitro group.Tertiary amine.Tertiary amine | Primary amine | c1cncnc1.C1COCCN1.C1COCCN1.c1ccc2[nH]cnc2c1.c1ccc2[nH]cnc2c1.c1cncnc1 | c1ccc2[nH]cnc2c1.c1cncnc1 | c1ccc2[nH]cnc2c1.c1cncnc1.C1COCC[NH]1.C1COCC[NH]1 | HF | null | null | null | O=[N+]([O-])c1ccc2c(c1)nc(C(F)F)n2-c1nc(N2CCOCC2)cc(N2CCOCC2)n1.O=[N+]([O-])c1ccc2nc(C(F)F)n(-c3nc(N4CCOCC4)cc(N4CCOCC4)n3)c2c1>>Nc1ccc2nc(C(F)F)n(-c3nc(N4CCOCC4)cc(N4CCOCC4)n3)c2c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d9ba8b48dcf744dfb37d5d925a99469d | C[C@@H]1OCCN(c2nc(N3CCOCC3)nc(-n3c(C(F)F)nc4cc(O[Si](C)(C)C(C)(C)C)ccc43)n2)[C@@H]1C>>C[C@@H]1OCCN(c2nc(N3CCOCC3)nc(-n3c(C(F)F)nc4cc(O)ccc43)n2)[C@@H]1C | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC.FC(C=1NC2=C(N1)C=CC=C2)F.FC(C1=NC2=C(N1C1=NC(=NC(=N1)N1[C@@H]([C@@H](OCC1)C)C)N1CCOCC1)C=CC(=C2)O[Si](C)(C)C(C)(C)C)F.FC(C=1NC2=C(N1)C(=C(C(=C2O[SiH3])C(C)(C)C)C)C)F>>FC(C1=NC2=C(N1C1=NC(=NC(=N1)N1[C@@H]([C@@H](OCC1)C)C)N1CCOCC1)C=CC(=C2)O)F | CC(C)(C)[Si](C)(C)[O:27][c:26]1[cH:25][c:24]2[n:23][c:19]([CH:20]([F:21])[F:22])[n:18](-[c:17]3[n:16][c:9]([N:10]4[CH2:11][CH2:12][O:13][CH2:14][CH2:15]4)[n:8][c:7]([N:6]4[CH2:5][CH2:4][O:3][C@@H:2]([CH3:1])[C@H:32]4[CH3:33])[n:31]3)[c:30]2[cH:29][cH:28]1>>[CH3:1][C@@H:2]1[O:3][CH2:4][CH2:5][N:6]([c:7]2[n:8][c:9]([N:10... | C[C@@H]1OCCN(c2nc(N3CCOCC3)nc(-n3c(C(F)F)nc4cc(O[Si](C)(C)C(C)(C)C)ccc43)n2)[C@@H]1C | C[C@@H]1OCCN(c2nc(N3CCOCC3)nc(-n3c(C(F)F)nc4cc(O)ccc43)n2)[C@@H]1C | null | null | O.C1CCOC1 | Deprotection | Alcohol deprotection from silyl ethers | e70131badc7d7d580ed75b2dfb3ce6df2a5f496b2119611cf5354e1267babe73 | b09ece7bccc3ff762f4ff5407ad846fffba6d6a63735853c86a86d29904f54ed | c1ccc2c(c1)ncn2-c1nc(N2CCOCC2)nc(N2CCOCC2)n1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 79 | [{"value": 79.0, "product": "FC(C1=NC2=C(N1C1=NC(=NC(=N1)N1[C@@H]([C@@H](OCC1)C)C)N1CCOCC1)C=CC(=C2)O)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | In accordance with the procedure of the Example 4 except that 2-difluoromethylbenzimidazole in (1) of the Example 4 was replaced by 2-difluoromethyl-5-tert-butyldimethyl-silyloxybenzimidazole, obtained was 2-(2-difluoromethyl-5-tert-butyldimethylsilyloxybenzimidazol-1-yl)-4-(cis-2,3-dimethylmorpholino)-6-morpholino-1,3... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Aromatic alcohol | null | null | C1COCC[NH]1.c1ncncn1.C1COCC[NH]1.c1ccc2[nH]cnc2c1 | Other | O.C1CCOC1 | null | 0.5 | C[C@@H]1OCCN(c2nc(N3CCOCC3)nc(-n3c(C(F)F)nc4cc(O[Si](C)(C)C(C)(C)C)ccc43)n2)[C@@H]1C>O.C1CCOC1>C[C@@H]1OCCN(c2nc(N3CCOCC3)nc(-n3c(C(F)F)nc4cc(O)ccc43)n2)[C@@H]1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1e6a466c51cc492e9ad3e90bd07420f0 | CC(C)(C)[Si](C)(C)Oc1ccc2c(c1)nc(C(F)F)n2-c1nc(N2CCOCC2)cc(N2CCOCC2)n1>>Oc1ccc2c(c1)nc(C(F)F)n2-c1nc(N2CCOCC2)cc(N2CCOCC2)n1 | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC.FC(C=1NC2=C(N1)C=CC=C2)F.FC(C1=NC2=C(N1C1=NC(=CC(=N1)N1CCOCC1)N1CCOCC1)C=CC(=C2)O[Si](C)(C)C(C)(C)C)F.FC(C=1NC2=C(N1)C=CC(=C2)O[Si](C)(C)C(C)(C)C)F>>FC(C1=NC2=C(N1C1=NC(=CC(=N1)N1CCOCC1)N1CCOCC1)C=CC(=C2)O)F | CC(C)(C)[Si](C)(C)[O:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[n:8][c:9]([CH:10]([F:11])[F:12])[n:13]2-[c:14]1[n:15][c:16]([N:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)[cH:23][c:24]([N:25]2[CH2:26][CH2:27][O:28][CH2:29][CH2:30]2)[n:31]1>>[OH:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[n:8][c:9]([CH:10]([F:11])[F:12])[n:1... | CC(C)(C)[Si](C)(C)Oc1ccc2c(c1)nc(C(F)F)n2-c1nc(N2CCOCC2)cc(N2CCOCC2)n1 | Oc1ccc2c(c1)nc(C(F)F)n2-c1nc(N2CCOCC2)cc(N2CCOCC2)n1 | null | null | O.C1CCOC1 | Deprotection | Alcohol deprotection from silyl ethers | e70131badc7d7d580ed75b2dfb3ce6df2a5f496b2119611cf5354e1267babe73 | b09ece7bccc3ff762f4ff5407ad846fffba6d6a63735853c86a86d29904f54ed | c1ccc2c(c1)ncn2-c1nc(N2CCOCC2)cc(N2CCOCC2)n1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 93 | [{"value": 93.0, "product": "FC(C1=NC2=C(N1C1=NC(=CC(=N1)N1CCOCC1)N1CCOCC1)C=CC(=C2)O)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | In accordance with the procedure of the Example 1 except that 2-difluoromethylbenzimidazole in (1) of the Example 1 was replaced by 2-difluoromethyl-5-tert-butyldimethylsilyloxybenzimidazole, obtained was 2-(2-difluoromethyl-5-tert-butyldimethylsilyloxybenzimidazol-1-yl)-4,6-dimorpholinopyrimidine. 0.55 g (1.0 mmol) of... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Aromatic alcohol | null | null | c1ccc2nc[nH]c2c1.c1cncnc1.C1COCC[NH]1.C1COCC[NH]1 | Other | O.C1CCOC1 | null | 0.5 | CC(C)(C)[Si](C)(C)Oc1ccc2c(c1)nc(C(F)F)n2-c1nc(N2CCOCC2)cc(N2CCOCC2)n1>O.C1CCOC1>Oc1ccc2c(c1)nc(C(F)F)n2-c1nc(N2CCOCC2)cc(N2CCOCC2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b005b6f337a44f94b9a0bf0c978e4792 | Cc1cc(C)cc(-c2cc3ncnc(O)c3s2)c1.O=P(Cl)(Cl)Cl>>Cc1cc(C)cc(-c2cc3ncnc(Cl)c3s2)c1 | OC=1C2=C(N=CN1)C=C(S2)C2=CC(=CC(=C2)C)C.C(C)(C)N(CC)C(C)C.P(=O)(Cl)(Cl)Cl>>ClC=1C2=C(N=CN1)C=C(S2)C2=CC(=CC(=C2)C)C | O[c:14]1[n:13][cH:12][n:11][c:10]2[cH:9][c:8](-[c:7]3[cH:6][c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:18]3)[s:17][c:16]21.O=P(Cl)(Cl)[Cl:15]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[cH:6][c:7](-[c:8]2[cH:9][c:10]3[n:11][cH:12][n:13][c:14]([Cl:15])[c:16]3[s:17]2)[cH:18]1 | Cc1cc(C)cc(-c2cc3ncnc(O)c3s2)c1.O=P(Cl)(Cl)Cl | Cc1cc(C)cc(-c2cc3ncnc(Cl)c3s2)c1 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | c5bd6f721b4a732e8f530df375174d18cc558944df73419315d063a44729e72f | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(-c2cc3ncncc3s2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:[c:8]:[#16;a:9]:[c:10]:2:1>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6]2:[c:7]:[c:8]:[#16;a:9]:[c:10]:2:1 | null | [] | 100 | CELSIUS | null | null | The hydroxy compound prepared in Step 1 was treated with phosphorous oxychloride (150 mL) and diisopropylethylamine (2 mL). The mixture was then heated at 100° C. for 4 hours. The solvents were evaporated under reduced pressure and the residue was carefully treated with ice water. The resulting solid was filtered off a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ncc2sccc2n1 | c1ncc2sccc2n1 | c1ccccc1.c1ncc2sccc2n1 | HCl | null | 100 | null | Cc1cc(C)cc(-c2cc3ncnc(O)c3s2)c1.O=P(Cl)(Cl)Cl>>Cc1cc(C)cc(-c2cc3ncnc(Cl)c3s2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4d12ac80a56d479baf43142f1db2788d | COC(=O)CN.O=C1CCCCCC1>>O=C(O)CNC1CCCCCC1 | C1(CCCCCC1)=O.COC(CN)=O>>C1(CCCCCC1)NCC(=O)O | C[O:3][C:2](=[O:1])[CH2:4][NH2:5].O=[C:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1>>[O:1]=[C:2]([OH:3])[CH2:4][NH:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1 | COC(=O)CN.O=C1CCCCCC1 | O=C(O)CNC1CCCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 7ea5121718be1ecc742f905d3734383e45859d783523b6197248271234304b8c | 54e31965a8ebe7ac0cdd3327194966ab957cb5aa1af511ad8ea20929465150a5 | C1CCCCCC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[NH2;D1;+0:5].O=[C;H0;D3;+0:6](-[C:7]-[C:8])-[C:9]-[C:10]>>[C:8]-[C:7]-[CH;D3;+0:6](-[NH;D2;+0:5]-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])-[C:9]-[C:10] | null | [] | null | null | null | null | N-Cycloheptylglycine was synthesized by reductive amination of cycloheptanone with glycine methyl ester following the procedure described in Gera et al., Immunopharmacology. 33:174–177 (1996). The crude product was converted to the N-Boc derivative (mp, 89–90° C.).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine | Carboxylic acid.Secondary amine | C1CCCCCC1 | C1CCCCCC1 | C1CCCCCC1 | HO- | null | null | null | COC(=O)CN.O=C1CCCCCC1>>O=C(O)CNC1CCCCCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fa704ecb2dbe442f93a503e20069bbcd | O=C(O)C=Cc1ccncc1>>O=C(O)CCC1CCNCC1 | N1=CC=C(C=C1)C=CC(=O)O.[H][H]>>N1CCC(CC1)CCC(=O)O | [O:1]=[C:2]([OH:3])[CH:4]=[CH:5][c:6]1[cH:7][cH:8][n:9][cH:10][cH:11]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1 | O=C(O)C=Cc1ccncc1 | O=C(O)CCC1CCNCC1 | null | [Ru] | O.N | Reduction | OtherReaction | 8a6c78a63989dd47e282eb33ae5ce6bfcead5defaa210963e9125c31297ee886 | 2b7f370a519e29b4dede190aa36b37f30822496e32f2c8bfa9736e631bde52e2 | C1CCNCC1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH;D2;+0:4]=[CH;D2;+0:5]-[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[cH;D2;+0:8]:[n;H0;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:1>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH;D3;+0:6]1-[CH2;D2;+0:7]-[CH2;D2;+0:8]-[NH;D2;+0:9]-[CH2;D2;+0:10]-[CH2;D2;+0:11]-1 | 100 | [{"value": 100.0, "product": "N1CCC(CC1)CCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.7, "product": "N1CCC(CC1)CCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 3-pyridin4-yl-acrylic acid (4.20 g, 28.0 mmol) in water (50 mL) and ammonia (aq, 25%, 4 mL) was hydrogenated at 60 bar in a high pressure steel autoclave in presence of ruthenium (5% on alumina, 439 mg). When hydrogen pressure remained constant (3 days) the catalyst was removed from the reaction mixture b... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary amine | c1ccncc1 | C1CCNCC1 | C1CCNCC1 | null | [Ru].O.N | null | null | O=C(O)C=Cc1ccncc1>[Ru].O.N>O=C(O)CCC1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-503d8f8f951340d2a25790799eb1eb45 | CC(C)(C)OC(=O)N1CCC(CC(CSCc2ccccc2)C(=O)O)CC1>>CC(C)(C)OC(=O)N1CCC(CC(CS)C(=O)O)CC1 | [Cl-].[NH4+].[Na].C(C)(C)(C)OC(=O)N1CCC(CC1)CC(CSCC1=CC=CC=C1)C(=O)O.N>>C(C)(C)(C)OC(=O)N1CCC(CC1)CC(CS)C(=O)O | c1ccc(C[S:15][CH2:14][CH:13]([CH2:12][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:20][CH2:19]2)[C:16](=[O:17])[OH:18])cc1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][CH:13]([CH2:14][SH:15])[C:16](=[O:17])[OH:18])[CH2:19][CH2:20]1 | CC(C)(C)OC(=O)N1CCC(CC(CSCc2ccccc2)C(=O)O)CC1 | CC(C)(C)OC(=O)N1CCC(CC(CS)C(=O)O)CC1 | null | null | C1CCOC1 | Deprotection | OtherReaction | 8ede657ec13277980662af24e502b19505abce30b66d95f1c70163f9a07caa47 | d0652a71194d478b6d145ca18f942c41b2e93fe2aec41553ada2c2882bb6a1a5 | C1CCNCC1 | [O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]-[C:5]-[S;H0;D2;+0:6]-C-c1:c:c:c:c:c:1>>[O;D1;H0:1]=[C:2](-[O;D1;H1:3])-[C:4]-[C:5]-[SH;D1;+0:6] | 100.7 | [{"value": 100.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)CC(CS)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.7, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)CC(CS)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Sodium metal (513 mg, 22.5 mmol) was added in portions during 5 min. to a solution of 4-(3-Benzylsulfanyl-2-carboxy-propyl)-piperidine-1-carboxylic acid tert-butyl ester (0.9 g, 2.29 mmol) in THF (45 mL) and liquid ammonia (50 mL) at −60° C. under argon. After stirring for 15 min. ammonium chloride (1.7 g, 31.5 mmol) w... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Aliphatic thiol | c1ccccc1 | null | C1CC[NH]CC1 | Other | C1CCOC1 | null | null | CC(C)(C)OC(=O)N1CCC(CC(CSCc2ccccc2)C(=O)O)CC1>C1CCOC1>CC(C)(C)OC(=O)N1CCC(CC(CS)C(=O)O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-65be9be147ec4d6cba76109aff30097f | O=C(O)C(CS)CC1CCNCC1.O=C(O)C(F)(F)F>>CC(=O)N1CCC(CC(CS)C(=O)O)CC1 | OC(=O)C(F)(F)F.SCC(C(=O)O)CC1CCNCC1>>C(C)(=O)N1CCC(CC1)CC(C(=O)O)CS | [NH:4]1[CH2:5][CH2:6][CH:7]([CH2:8][CH:9]([CH2:10][SH:11])[C:12](=[O:13])[OH:14])[CH2:15][CH2:16]1.O[C:2]([C:1](F)(F)F)=[O:3]>>[CH3:1][C:2](=[O:3])[N:4]1[CH2:5][CH2:6][CH:7]([CH2:8][CH:9]([CH2:10][SH:11])[C:12](=[O:13])[OH:14])[CH2:15][CH2:16]1 | O=C(O)C(CS)CC1CCNCC1.O=C(O)C(F)(F)F | CC(=O)N1CCC(CC(CS)C(=O)O)CC1 | null | null | C(C)(=O)OC(C)=O | Acylation | OtherReaction | 4e665ada278c24eacee09f9a3c04c28279e21a3099f8c777c866698d929a6b64 | a253cb3278e717ca1fbd16abc111e74dcfbf11461b2eecdac44191f9b4019e83 | C1CCNCC1 | F-[C;H0;D4;+0:1](-F)(-F)-[C;H0;D3;+0:2](-O)=[O;D1;H0:3].[C:4]-[C:5]-[NH;D2;+0:6]-[C:7]-[C:8]>>[C:4]-[C:5]-[N;H0;D3;+0:6](-[C;H0;D3;+0:2](-[CH3;D1;+0:1])=[O;D1;H0:3])-[C:7]-[C:8] | 80.2 | [{"value": 80.0, "product": "C(C)(=O)N1CCC(CC1)CC(C(=O)O)CS", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.2, "product": "C(C)(=O)N1CCC(CC1)CC(C(=O)O)CS", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 2-Mercaptomethyl-3-piperidin-4-yl-propionic acid TFA salt (0.1 g, 0.32 mmol) in acetic anhydride (2 mL) was stirred over night under argon and then concentrated under reduced pressure. Purification by HPLC (10→50% acetonitrile, 0.1% TFA in water) gave the title compound (63 mg, 80%).
Conditions: See react... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | Other | C(C)(=O)OC(C)=O | null | null | O=C(O)C(CS)CC1CCNCC1.O=C(O)C(F)(F)F>C(C)(=O)OC(C)=O>CC(=O)N1CCC(CC(CS)C(=O)O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0c62e6cebadc470dbabcf15e2d3a6fe2 | BrC(Br)(Br)Br.CC(C)(C)OC(=O)N1CCC(CO)CC1>>CC(C)(C)OC(=O)N1CCC(CBr)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)CO.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Br)(Br)(Br)Br>>C(C)(C)(C)OC(=O)N1CCC(CC1)CBr | BrC(Br)(Br)[Br:13].O[CH2:12][CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:15][CH2:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][Br:13])[CH2:14][CH2:15]1 | BrC(Br)(Br)Br.CC(C)(C)OC(=O)N1CCC(CO)CC1 | CC(C)(C)OC(=O)N1CCC(CBr)CC1 | null | null | C(C)OCC | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | C1CCNCC1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[C:3](-[C:4])-[C:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](-[C:4])-[C:5] | 73.1 | [{"value": 73.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)CBr", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.1, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)CBr", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | To a solution 4-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (8.75 g, 40.64 mmol) in diethyl ether (200 mL) at 0° C. under nitrogen. were added triphenyl phosphine (21.32 g, 81.28 mmol) and carbon tetrabromide (26.96 g, 81.28 mmol). The mixture was allowed to warm to room temperature and stirred under ni... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | C1CC[NH]CC1 | HBr | C(C)OCC | null | 48 | BrC(Br)(Br)Br.CC(C)(C)OC(=O)N1CCC(CO)CC1>C(C)OCC>CC(C)(C)OC(=O)N1CCC(CBr)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3766d5d750f448b4a39ea86404d088d3 | CC(C)(C)OC(=O)N1CCC(CBr)CC1.CCOP(=O)(CC(=O)OC(C)(C)C)OCC.O>>CCOP(=O)(CC(=O)OC(C)(C)C)OCC.CCOP(=O)(OCC)C(CC1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)N1CCC(CC1)CBr.C(C)OP(=O)(OCC)CC(=O)OC(C)(C)C.[H-].[Na+].O>>C(C)(C)(C)OC(=O)N1CCC(CC1)CC(P(=O)(OCC)OCC)C(=O)OC(C)(C)C.C(C)OP(=O)(OCC)CC(=O)OC(C)(C)C | Br[CH2:26][CH:27]1[CH2:28][CH2:29][N:30]([C:31](=[O:32])[O:33][C:34]([CH3:25])([CH3:35])[CH3:37])[CH2:38][CH2:39]1.[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3:18])[CH3:24])[O:14][CH2:15][CH3:16].[OH2:41]>>[CH3:1][CH2:2][O:3][P:4](=[O:5])([CH2:6][C:7](=[O:8])[O:9][C:10]([CH3:11])([CH3... | CC(C)(C)OC(=O)N1CCC(CBr)CC1.CCOP(=O)(CC(=O)OC(C)(C)C)OCC.O | CCOP(=O)(CC(=O)OC(C)(C)C)OCC.CCOP(=O)(OCC)C(CC1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OC(C)(C)C | null | null | CN(C)C=O | Acylation | OtherReaction | a3202466c5051a4246443792e706fa69b83b341c168f44c95f8bcecc2c14df33 | 8c255a91e9b3cc01ee961564874897d7dcff087be6435234c9cc2ffd1a71bc7f | C1CCNCC1 | Br-[CH2;D2;+0:1]-[C:2]1-[C:3]-[C:4]-[#7:5](-[C:6](=[O;D1;H0:7])-[#8:8]-[C;H0;D4;+0:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[CH3;D1;+0:12])-[C:13]-[C:14]-1.[C:15]-[C:16](=[O;D1;H0:17])-[#8:18]-[C;H0;D4;+0:19](-[C;D1;H3:20])(-[CH3;D1;+0:21])-[CH3;D1;+0:22].[OH2;D0;+0:23]>>[#8:24]-[C:25](=[O;H0;D1;+0:23])-[CH;D3;+0:12](-[CH2;D2;... | null | [] | 0 | CELSIUS | 0.5 | HOUR | tert-Butyl diethylphosphonoacetate (75.0 g, 297.32 mmol) was added dropwise to a suspension of sodium hydride (8.03 g, 334.58 mmol) in DMF (450 mL) at 0° C. under nitrogen. The mixture was stirred at 0° C. for 0.5 h and at room temperature for 0.5 h. 4-bromomethyl-piperidine-1-carboxylic acid tert-butyl ester (20.68 g,... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ether.Boc.Boc | Ester.Ester.Ether.Boc.Boc.Boc | null | null | C1CC[NH]CC1 | Br- | CN(C)C=O | 0 | 0.5 | CC(C)(C)OC(=O)N1CCC(CBr)CC1.CCOP(=O)(CC(=O)OC(C)(C)C)OCC.O>CN(C)C=O>CCOP(=O)(CC(=O)OC(C)(C)C)OCC.CCOP(=O)(OCC)C(CC1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c358a21ea0d542caa5807df5d9aaba60 | CC(C)CC=C(CC1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OC(C)(C)C.COc1ccc(CS)cc1>>COc1ccc(CSC(CC(C)C)C(CC2CCN(C(=O)OC(C)(C)C)CC2)C(=O)OC(C)(C)C)cc1 | O.C(C)(C)(C)OC(=O)N1CCC(CC1)CC(=CCC(C)C)C(=O)OC(C)(C)C.C([O-])([O-])=O.[K+].[K+].COC1=CC=C(C=C1)CS>>C(C)(C)(C)OC(=O)N1CCC(CC1)CC(C(CC(C)C)SCC1=CC=C(C=C1)OC)C(=O)OC(C)(C)C | [CH:9]([CH2:10][CH:11]([CH3:12])[CH3:13])=[C:14]([CH2:15][CH:16]1[CH2:17][CH2:18][N:19]([C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:27][CH2:28]1)[C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][SH:8])[cH:36][cH:37]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]... | CC(C)CC=C(CC1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OC(C)(C)C.COc1ccc(CS)cc1 | COc1ccc(CSC(CC(C)C)C(CC2CCN(C(=O)OC(C)(C)C)CC2)C(=O)OC(C)(C)C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | d6786c551347d89580cd19199d8055616f405cdef22ea256b5a523ba65083594 | e024304228c7143d5ec452c855d5c53cce598d20ddcea996ef240d59c49deaa3 | c1ccc(CSCCCC2CCNCC2)cc1 | [C:1]-[C:2]-[CH;D2;+0:3]=[C;H0;D3;+0:4](-[C:5]-[C:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13].[SH;D1;+0:14]-[C:15]-[c:16]>>[C:1]-[C:2]-[CH;D3;+0:3](-[S;H0;D2;+0:14]-[C:15]-[c:16])-[CH;D3;+0:4](-[C:5]-[C:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13] | 63 | [{"value": 63.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)CC(C(CC(C)C)SCC1=CC=C(C=C1)OC)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)CC(C(CC(C)C)SCC1=CC=C(C=C1)OC)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-(2-tert-butoxycarbonyl-5-methyl-hex-2-enyl)-piperidine-1-carboxylic acid tert-butyl ester (2.0 g, 5.24 mmol) in DMF (5 mL) was added to a mixture of potassium carbonate (0.54 g, 3.93 mmol) and 4-methoxy-α-toluenethiol (1.17 g, 10.48 mmol) in DMF (50 mL) under nitrogen. The mixture was refluxed for 5 h a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aliphatic thiol | Ester.Monosulfide | null | null | c1ccccc1.C1CC[NH]CC1 | null | CN(C)C=O | null | null | CC(C)CC=C(CC1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OC(C)(C)C.COc1ccc(CS)cc1>CN(C)C=O>COc1ccc(CSC(CC(C)C)C(CC2CCN(C(=O)OC(C)(C)C)CC2)C(=O)OC(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6952928057324816a1938954f85bcf59 | CC(C)(C)OC(=O)C(=CCc1ccccc1)CC1CCN(C(=O)OC(C)(C)C)CC1.COc1ccc(CS)cc1>>COc1ccc(CSC(Cc2ccccc2)C(CC2CCN(C(=O)OC(C)(C)C)CC2)C(=O)OC(C)(C)C)cc1 | O.C(C)(C)(C)OC(=O)N1CCC(CC1)CC(=CCC1=CC=CC=C1)C(=O)OC(C)(C)C.C([O-])([O-])=O.[K+].[K+].COC1=CC=C(C=C1)CS>>C(C)(C)(C)OC(=O)N1CCC(CC1)CC(C(CC1=CC=CC=C1)SCC1=CC=C(C=C1)OC)C(=O)OC(C)(C)C | [CH:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)=[C:17]([CH2:18][CH:19]1[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]1)[C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][SH:8])[cH:39][cH:40]1>>[CH3:1][O:2][c:3]... | CC(C)(C)OC(=O)C(=CCc1ccccc1)CC1CCN(C(=O)OC(C)(C)C)CC1.COc1ccc(CS)cc1 | COc1ccc(CSC(Cc2ccccc2)C(CC2CCN(C(=O)OC(C)(C)C)CC2)C(=O)OC(C)(C)C)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | d6786c551347d89580cd19199d8055616f405cdef22ea256b5a523ba65083594 | e024304228c7143d5ec452c855d5c53cce598d20ddcea996ef240d59c49deaa3 | c1ccc(CSC(CCC2CCNCC2)Cc2ccccc2)cc1 | [C:1]-[C:2]-[C;H0;D3;+0:3](=[CH;D2;+0:4]-[C:5]-[c:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13].[SH;D1;+0:14]-[C:15]-[c:16]>>[C:1]-[C:2]-[CH;D3;+0:3](-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13])-[CH;D3;+0:4](-[C:5]-[c:6])-[S;H0;D2;+0:14]-[C:15]-[c:16] | 50 | [{"value": 50.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)CC(C(CC1=CC=CC=C1)SCC1=CC=C(C=C1)OC)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 50.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)CC(C(CC1=CC=CC=C1)SCC1=CC=C(C=C1)OC)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false... | 75 | CELSIUS | null | null | 4-(2-tert-Butoxycarbonyl4-phenyl-but-2-enyl)-piperidine-1-carboxylic acid tert-butyl ester (0.8 g, 1.93 mmol) in DMF (10 mL) was added to a suspension of potassium carbonate (0.20 g, 1.44 mmol) ) and 4-methoxy-α-toluenethiol (0.54 mL, 3.85 mmol) in DMF (10 mL) under nitrogen. The mixture was heated to 75° C. for 24 h a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Aliphatic thiol | Ester.Monosulfide | null | null | c1ccccc1.c1ccccc1.C1CC[NH]CC1 | null | CN(C)C=O | 75 | null | CC(C)(C)OC(=O)C(=CCc1ccccc1)CC1CCN(C(=O)OC(C)(C)C)CC1.COc1ccc(CS)cc1>CN(C)C=O>COc1ccc(CSC(Cc2ccccc2)C(CC2CCN(C(=O)OC(C)(C)C)CC2)C(=O)OC(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4c91d3469d9e4eeeb3d52c80632ed8db | CCOCC.Cc1ccnc(N)c1>>CC(=O)Nc1cc(C)ccn1 | NC1=NC=CC(=C1)C.C(C)OCC>>CC1=CC(=NC=C1)NC(C)=O | CC[O:3][CH2:2][CH3:1].[NH2:4][c:5]1[cH:6][c:7]([CH3:8])[cH:9][cH:10][n:11]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][c:7]([CH3:8])[cH:9][cH:10][n:11]1 | CCOCC.Cc1ccnc(N)c1 | CC(=O)Nc1cc(C)ccn1 | null | null | C(C)(=O)OC(C)=O | Acylation | OtherReaction | 003d6e284475e7d4fe43f9e91e4ad7ca9bf4d7f2029a8fe4e8eed7dbde0fdef0 | 25423bd5162c5be916302ae1ac632b1f2d5d912d0ee7eadf1b5b1259507dc6c3 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[CH2;D2;+0:2]-[C;D1;H3:3].[NH2;D1;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[C;D1;H3:3]-[C;H0;D3;+0:2](=[O;H0;D1;+0:1])-[NH;D2;+0:4]-[c:5](:[c:6]):[#7;a:7]:[c:8] | 95 | [{"value": 95.0, "product": "CC1=CC(=NC=C1)NC(C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Amino4-methylpyridine (99.0 g, 91.5 mmol) in acetic anhydride (250 mL) was warmed to 70° C. for two h. The mixture was cooled to room temperature and diethyl ether (100 mL) added. The product crystallized as white needle crystals. Filtering and drying in vacuo afforded N-(4-methyl-pyridin-2-yl)-acetamide (130 g, 95%)... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary amide | null | null | c1ccncc1 | Other | C(C)(=O)OC(C)=O | null | null | CCOCC.Cc1ccnc(N)c1>C(C)(=O)OC(C)=O>CC(=O)Nc1cc(C)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cecb5bf832084ef5a6421240cee3dddf | CC(=O)Nc1cc(C(=O)O)ccn1.CCO>>CCOC(=O)c1ccnc(N)c1 | C(C)(=O)NC=1C=C(C(=O)O)C=CN1.C(=O)(O)[O-].[Na+].C(C)O>>C(C)OC(C1=CC(=NC=C1)N)=O | CC(=O)[NH:11][c:10]1[n:9][cH:8][cH:7][c:6]([C:4](O)=[O:5])[cH:12]1.[CH3:1][CH2:2][OH:3]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][n:9][c:10]([NH2:11])[cH:12]1 | CC(=O)Nc1cc(C(=O)O)ccn1.CCO | CCOC(=O)c1ccnc(N)c1 | null | null | null | Acylation | OtherReaction | db4aad5bc6eb04613ddfb9a3aea41fadd2fa9a025207774fa644fb14d470fda3 | 1fa52715508855a72f553ab5455008c4c9437321a1b1d5fc5200958d9ee092d1 | c1ccncc1 | C-C(=O)-[NH;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[c:5]:[c:6](-[C;H0;D3;+0:7](-O)=[O;D1;H0:8]):[c:9]:1.[C;D1;H3:10]-[C:11]-[OH;D1;+0:12]>>[C;D1;H3:10]-[C:11]-[O;H0;D2;+0:12]-[C;H0;D3;+0:7](=[O;D1;H0:8])-[c:6]1:[c:9]:[c:2](-[NH2;D1;+0:1]):[#7;a:3]:[c:4]:[c:5]:1 | 79 | [{"value": 79.0, "product": "C(C)OC(C1=CC(=NC=C1)N)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Acetylamino-isonicotinic acid (10.8 g, 60.0 mmol) was suspended in ethanol (150 mL) and BF3OEt2 (22 mL, 138 mmol) was added. The mixture was refluxed overnight, and after cooling to room temperature 10% NaHCO3 (250 mL) was added. The product was extracted with chloroform and the combined organic extracts were washed ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amide.Primary alcohol | Ester.Primary amine | null | null | c1ccncc1 | HO- | null | null | null | CC(=O)Nc1cc(C(=O)O)ccn1.CCO>>CCOC(=O)c1ccnc(N)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e22be225eb1c4553a6fd980d9b34a803 | CCOC(=O)c1ccnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c1>>CC(C)(C)OC(=O)Nc1cc(CO)ccn1 | C(C)OC(C1=CC(=NC=C1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>C(C)(C)(C)OC(NC1=NC=CC(=C1)CO)=O | CCO[C:12]([c:11]1[cH:10][c:9]([N:8](C(=O)OC(C)(C)C)[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[n:16][cH:15][cH:14]1)=[O:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][c:11]([CH2:12][OH:13])[cH:14][cH:15][n:16]1 | CCOC(=O)c1ccnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c1 | CC(C)(C)OC(=O)Nc1cc(CO)ccn1 | null | null | C1CCOC1 | Reduction | OtherReaction | 20962d9bc1897de80b918f6efe4891a362b51f4c6f3af7bad47f6e2640fa482a | f7ff3a3ce995d934c8d2667c39df2283accf4ec6ad29f6be8bba5d4b604712d3 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3]1:[c:4]:[c:5](-[N;H0;D3;+0:6](-C(=O)-O-C(-C)(-C)-C)-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10](-[C;D1;H3:11])(-[C;D1;H3:12])-[C;D1;H3:13]):[#7;a:14]:[c:15]:[c:16]:1>>[C;D1;H3:11]-[C:10](-[C;D1;H3:12])(-[C;D1;H3:13])-[#8:9]-[C:7](=[O;D1;H0:8])-[NH;D2;+0:6]-[c:5]1:[#7;a:14]:[c:15]:[c:16]... | 86.4 | [{"value": 86.0, "product": "C(C)(C)(C)OC(NC1=NC=CC(=C1)CO)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.4, "product": "C(C)(C)(C)OC(NC1=NC=CC(=C1)CO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of to 2-[N,N-bis(tert-Butoxycarbonyl)amino]-isonicotinic acid ethyl ester (35.0 g, 95.5 mmol) in THF (350 mL) was treated with LiAlH4 (7.25 g, 191 mmol) and refluxed for 1 h under nitrogen. The reaction mixture was poured carefully onto crushed ice and the product extracted several times with CHCl3 and CHCl3... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ester.Ether.Substituted dicarboximide.Boc | Carbamic ester.Primary alcohol | null | null | c1ccncc1 | HO- | C1CCOC1 | null | null | CCOC(=O)c1ccnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c1>C1CCOC1>CC(C)(C)OC(=O)Nc1cc(CO)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0d78069ce36d4a58bfce4e19432cccc4 | BrC(Br)(Br)Br.CC(C)(C)OC(=O)Nc1cc(CO)ccn1>>CC(C)(C)OC(=O)Nc1cc(CBr)ccn1 | C(C)(C)(C)OC(NC1=NC=CC(=C1)CO)=O.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C(Br)(Br)(Br)Br>>C(C)(C)(C)OC(NC1=NC=CC(=C1)CBr)=O | BrC(Br)(Br)[Br:13].O[CH2:12][c:11]1[cH:10][c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[n:16][cH:15][cH:14]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][c:11]([CH2:12][Br:13])[cH:14][cH:15][n:16]1 | BrC(Br)(Br)Br.CC(C)(C)OC(=O)Nc1cc(CO)ccn1 | CC(C)(C)OC(=O)Nc1cc(CBr)ccn1 | null | null | C(Cl)Cl | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | c1ccncc1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | 82 | [{"value": 82.0, "product": "C(C)(C)(C)OC(NC1=NC=CC(=C1)CBr)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.0, "product": "C(C)(C)(C)OC(NC1=NC=CC(=C1)CBr)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | (4-Hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (8.00 g, 35.6 mmol) was dissolved in CH2Cl2 (150 mL) and treated with PPh3 (11.2 g, 42.8 mmol) under nitrogen. The reaction flask was cooled in an ice bath and CBr4 (14.2 g, 42.8 mmol) was added in small portions. The ice bath was removed after 30 min and th... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | c1ccncc1 | HBr | C(Cl)Cl | null | 8 | BrC(Br)(Br)Br.CC(C)(C)OC(=O)Nc1cc(CO)ccn1>C(Cl)Cl>CC(C)(C)OC(=O)Nc1cc(CBr)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-805b1be0b06a48d0ae30146f8f6f791f | CC(C)(C)OC(=O)Nc1cc(CBr)ccn1.CCOC(=O)CC(=O)OCC>>CCOC(=O)C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)OCC | C(C)(C)(C)OC(NC1=NC=CC(=C1)CBr)=O.[H-].[Na+].C(CC(=O)OCC)(=O)OCC>>C(C)OC(C(C(=O)OCC)CC1=CC(=NC=C1)NC(=O)OC(C)(C)C)=O | Br[CH2:7][c:8]1[cH:9][cH:10][n:11][c:12]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:22](=[O:23])[O:24][CH2:25][CH3:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][n:11][c:12]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:1... | CC(C)(C)OC(=O)Nc1cc(CBr)ccn1.CCOC(=O)CC(=O)OCC | CCOC(=O)C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)OCC | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | c1ccncc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1.[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[CH2;D2;+0:12]-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16]>>[C:8]-[#8:9]-[C:10](=[O;D1;H0:11])-[CH;D3;+0:12](-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1)-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16] | 62.7 | [{"value": 55.0, "product": "C(C)OC(C(C(=O)OCC)CC1=CC(=NC=C1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.7, "product": "C(C)OC(C(C(=O)OCC)CC1=CC(=NC=C1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a solution of NaH (80%, 0.17 g, 4.00 mmol) in THF (5 mL) at 0° C. under argon was added diethyl malonate (0.64 g, 4.00 mmol). After the mixture was stirred for 15 min the mixture was added to a refluxed mixture of (4-bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (1.00 g, 3.48 mmol) in THF (10 mL), and the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | c1ccncc1 | HBr | C1CCOC1 | null | 0.25 | CC(C)(C)OC(=O)Nc1cc(CBr)ccn1.CCOC(=O)CC(=O)OCC>C1CCOC1>CCOC(=O)C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d245cc3b73f8448fb111e6ba4a53d5dd | CCOC(=O)C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)OCC>>CCOC(=O)C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)O | [OH-].[K+].C(C)OC(C(C(=O)OCC)CC1=CC(=NC=C1)NC(=O)OC(C)(C)C)=O>>C(C)OC(C(C(=O)O)CC1=CC(=NC=C1)NC(=O)OC(C)(C)C)=O | CC[O:24][C:22]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][c:8]1[cH:9][cH:10][n:11][c:12]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[cH:21]1)=[O:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][n:11][c:12]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[cH:... | CCOC(=O)C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)OCC | CCOC(=O)C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)O | null | null | C(Cl)Cl.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 81.3 | [{"value": 81.0, "product": "C(C)OC(C(C(=O)O)CC1=CC(=NC=C1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.3, "product": "C(C)OC(C(C(=O)O)CC1=CC(=NC=C1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of KOH (0.19 g, 3.43 mmol) in ethanol (5 mL) was added to a solution of 2-(2-tert-butoxycarbonylamino-pyridin4-ylmethyl)-malonic acid diethyl ester (1.20 g, 3.27 mmol) in ethanol (5 mL) and methylene chloride (5 mL) at 0° C. The mixture was stirred for 18 h at room temperature. The mixture was concentrated u... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | Other | C(Cl)Cl.C(C)O | null | 18 | CCOC(=O)C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)OCC>C(Cl)Cl.C(C)O>CCOC(=O)C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d548d65a3035443ebaa3c97adc92d402 | CCOC(=O)C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)O>>C=C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)OCC | C(C)NCC.C(C)OC(C(C(=O)O)CC1=CC(=NC=C1)NC(=O)OC(C)(C)C)=O.C=O>>C(C)OC(C(=C)CC1=CC(=NC=C1)NC(=O)OC(C)(C)C)=O | O=[C:1](O)[CH:2]([CH2:3][c:4]1[cH:5][cH:6][n:7][c:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17]1)[C:18](=[O:19])[O:20][CH2:21][CH3:22]>>[CH2:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][n:7][c:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17]1)[C:18](=[O:19])[O:20][CH2:21][CH3:22... | CCOC(=O)C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)O | C=C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)OCC | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 485594ce7bba157615ffbb01ccede84a4e638576571b5d04649a06f3d4b7bce0 | 55e5b5078322f9f4fb0a7e9b5fc8a8cb9084e9135b447b8c441ad0800765792e | c1ccncc1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3]-[c:4])-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8]>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:3]-[c:4] | 71.2 | [{"value": 71.0, "product": "C(C)OC(C(=C)CC1=CC(=NC=C1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.2, "product": "C(C)OC(C(=C)CC1=CC(=NC=C1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | HOUR | A solution of diethylamine (0.26 g, 2.67 mmol) in methylene chloride (4 mL) was added to a mixture of 2-(2-tert-butoxycarbonylamino-pyridin4-ylmethyl)-malonic acid monoethyl ester (0.90 g, 2.66 mmol) and 37% aq. solution of formaldehyde (0.24 g, 3.00 mmol) at 0° C. The mixture was stirred for 5 h at room temperature an... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ester.Vinyl | null | null | c1ccncc1 | Other | C(Cl)Cl | null | 5 | CCOC(=O)C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)O>C(Cl)Cl>C=C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c5acf6150bfe4f35aa8cbad2307fd951 | C=C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)OCC.CC(O)=S>>CCOC(=O)C(CSC(C)=O)Cc1ccnc(NC(=O)OC(C)(C)C)c1 | C(C)OC(C(=C)CC1=CC(=NC=C1)NC(=O)OC(C)(C)C)=O.C(C)N(CC)CC.C(C)(=S)O>>C(C)OC(C(CC1=CC(=NC=C1)NC(=O)OC(C)(C)C)CSC(C)=O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH2:7])[CH2:12][c:13]1[cH:14][cH:15][n:16][c:17]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26]1.[S:8]=[C:9]([CH3:10])[OH:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH2:12][c:13]1[cH:14][cH:15][n:16][c:17]([NH:18][C:19]... | C=C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)OCC.CC(O)=S | CCOC(=O)C(CSC(C)=O)Cc1ccnc(NC(=O)OC(C)(C)C)c1 | null | null | null | Protection | OtherReaction | 56aa090d67fbecbea8a1963579cc34949775a09653b2b2f2795c609c60e70c77 | 5a9b0d631147b21b844b3c73866d1d81ab543538a176ebae28118ae7e39e572f | c1ccncc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](-[OH;D1;+0:3])=[S;H0;D1;+0:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[C;H0;D3;+0:9](=[CH2;D1;+0:10])-[C:11]-[c:12]>>[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH;D3;+0:9](-[C:11]-[c:12])-[CH2;D2;+0:10]-[S;H0;D2;+0:4]-[C;H0;D3;+0:2](-[C;D1;H3:1])=[O;H0;D1;+0:3] | 100 | [{"value": 100.0, "product": "C(C)OC(C(CC1=CC(=NC=C1)NC(=O)OC(C)(C)C)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A solution of 2-(2-tert-butoxycarbonylamino-pyridin-4-ylmethyl)-acrylic acid ethyl ester (0.48 g, 1.57 mmol) and triethylamine (0.17 g, 1.64 mmol) was added to thioacetic acid (3 mL) at 0° C. under nitrogen. The mixture was stirred at room temperature for 4 h. The mixture was poured onto ice-water and extracted with CH... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Thiocarbonyl.Vinyl | Ester.Carbo-thioester | null | null | c1ccncc1 | null | null | null | 4 | C=C(Cc1ccnc(NC(=O)OC(C)(C)C)c1)C(=O)OCC.CC(O)=S>>CCOC(=O)C(CSC(C)=O)Cc1ccnc(NC(=O)OC(C)(C)C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6e298fbb1394474fb21851f588a962f4 | CCOC(=O)C(CSC(C)=O)Cc1ccnc(NC(=O)OC(C)(C)C)c1>>CCOC(=O)C(CSC(C)=O)Cc1ccnc(N)c1 | C(=O)(C(F)(F)F)O.C(C)OC(C(CC1=CC(=NC=C1)NC(=O)OC(C)(C)C)CSC(C)=O)=O>>C(C)OC(C(CC1=CC(=NC=C1)N)CSC(C)=O)=O | CC(C)(C)OC(=O)[NH:18][c:17]1[n:16][cH:15][cH:14][c:13]([CH2:12][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][S:8][C:9]([CH3:10])=[O:11])[cH:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH2:12][c:13]1[cH:14][cH:15][n:16][c:17]([NH2:18])[cH:19]1 | CCOC(=O)C(CSC(C)=O)Cc1ccnc(NC(=O)OC(C)(C)C)c1 | CCOC(=O)C(CSC(C)=O)Cc1ccnc(N)c1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 141.7 | [{"value": 100.0, "product": "C(C)OC(C(CC1=CC(=NC=C1)N)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 141.7, "product": "C(C)OC(C(CC1=CC(=NC=C1)N)CSC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 60 | MINUTE | TFA (0.5 mL) was added to a solution of 2-acetylsulfanylmethyl-3-(2-tert-butoxycarbonylamino-pyridin4-yl)-propionic acid ethyl ester (50 mg, 0.13 mmol) in methylene chloride under argon. The solution was stirred for 60 min and concentrated under reduced pressure to give crude 2-acetylsulfanylmethyl-3-(2-amino-pyridin-4... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccncc1 | HO- | C(Cl)Cl | null | 1 | CCOC(=O)C(CSC(C)=O)Cc1ccnc(NC(=O)OC(C)(C)C)c1>C(Cl)Cl>CCOC(=O)C(CSC(C)=O)Cc1ccnc(N)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4bf3e9ebafb04352b1ad44652b3c3909 | CCOC(=O)C(CSC(C)=O)Cc1ccnc(N)c1>>Nc1cc(CC(CS)C(=O)O)ccn1 | C(C)OC(C(CC1=CC(=NC=C1)N)CSC(C)=O)=O>>NC1=NC=CC(=C1)CC(C(=O)O)CS | CC[O:11][C:9]([CH:6]([CH2:5][c:4]1[cH:3][c:2]([NH2:1])[n:14][cH:13][cH:12]1)[CH2:7][S:8]C(C)=O)=[O:10]>>[NH2:1][c:2]1[cH:3][c:4]([CH2:5][CH:6]([CH2:7][SH:8])[C:9](=[O:10])[OH:11])[cH:12][cH:13][n:14]1 | CCOC(=O)C(CSC(C)=O)Cc1ccnc(N)c1 | Nc1cc(CC(CS)C(=O)O)ccn1 | null | null | Cl | Reduction | OtherReaction | 1bcd8cbb2f136b4bcba1690e9ba45c4e43c89ba76f0e22de82a7d3fe318c82a9 | 5654c46fe4cb226f88ec3c899c7f9be1825c357673ea686958f9ef4883ee1db3 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[S;H0;D2;+0:6]-C(-C)=O>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[C:4]-[C:5]-[SH;D1;+0:6] | 100 | [{"value": 100.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Acetylsulfanylmethyl-3-(2-amino-pyridin4-yl)-propionic acid ethyl ester (52 mg, 0.13 mmol) was dissolved in conc. HCl (2 mL) under argon. The solution was heated to reflux for 1 h. Concentration under reduced pressure gave the title compound as the hydrochloride salt (32 mg, 100%).
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Carbo-thioester | Carboxylic acid.Aliphatic thiol | null | null | c1ccncc1 | HO- | Cl | null | null | CCOC(=O)C(CSC(C)=O)Cc1ccnc(N)c1>Cl>Nc1cc(CC(CS)C(=O)O)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a2acfb645bed42be8eb04a3e474dcc98 | CCOCC.Nc1ccc(C(=O)O)cn1>>CCOC(=O)c1ccc(N)nc1 | NC1=NC=C(C=C1)C(=O)O.[OH-].[Na+].C(C)OCC.O=S(Cl)Cl.O=S(Cl)Cl.O=S(Cl)Cl>>C(C)OC(C1=CN=C(C=C1)N)=O | CCO[CH2:2][CH3:1].[OH:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[n:11][cH:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([NH2:10])[n:11][cH:12]1 | CCOCC.Nc1ccc(C(=O)O)cn1 | CCOC(=O)c1ccc(N)nc1 | null | null | C1CCOC1.CO.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 51b8a6656c0a2b883c9ef3d6e10f16e7a23403a54025d10a356d536fd60cd751 | c9da2d501363e26e3362b4d92445c316ae4db0a7128a4caa823650c7a4fa5893 | c1ccncc1 | C-C-O-[CH2;D2;+0:1]-[C;D1;H3:2].[#7;a:3]:[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[#7;a:3]:[c:4]:[c:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-[CH2;D2;+0:1]-[C;D1;H3:2] | 97 | [{"value": 97.0, "product": "C(C)OC(C1=CN=C(C=C1)N)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2-Amino-5-pyridinecarboxylic acid (25.0 g, 181 mmol) was suspended in ethanol (190 mL) and SOCl2 (15 mL, 206 mmol) was added. The mixture was refluxed for 10 hs and more SOCl2 (16 mL) was added. After 3 days with reflux (and more SOCl2 (10 mL) added each day), the reaction mixture was cooled to room temperature and die... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether | Ester | null | null | c1ccncc1 | HO- | C1CCOC1.CO.C(C)O | null | 1 | CCOCC.Nc1ccc(C(=O)O)cn1>C1CCOC1.CO.C(C)O>CCOC(=O)c1ccc(N)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-974d6f3d98044b19b9a4be784b331090 | CCOC(=O)c1ccc(NC(=O)OC(C)(C)C)nc1>>CC(C)(C)OC(=O)Nc1ccc(CO)cn1 | C(C)OC(C1=CN=C(C=C1)NC(=O)OC(C)(C)C)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-]>>C(C)(C)(C)OC(NC1=NC=C(C=C1)CO)=O | CCO[C:13]([c:12]1[cH:11][cH:10][c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[n:16][cH:15]1)=[O:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][OH:14])[cH:15][n:16]1 | CCOC(=O)c1ccc(NC(=O)OC(C)(C)C)nc1 | CC(C)(C)OC(=O)Nc1ccc(CO)cn1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccncc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 68.1 | [{"value": 68.0, "product": "C(C)(C)(C)OC(NC1=NC=C(C=C1)CO)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.1, "product": "C(C)(C)(C)OC(NC1=NC=C(C=C1)CO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | To a stirred solution of 6-tert-butoxycarbonylamino-nicotinic acid ethyl ester (3.50 g, 13.1 mmol) in THF (20 mL) under nitrogen was added LiAlH4 (0.91 g, 24.0 mmol) in THF (20 mL) over a period of 2 h. The reaction mixture was stirred for 6 h, then NH4Cl (sat.) was added (carefully) until neutral solution. The mixture... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccncc1 | HO- | C1CCOC1 | null | 6 | CCOC(=O)c1ccc(NC(=O)OC(C)(C)C)nc1>C1CCOC1>CC(C)(C)OC(=O)Nc1ccc(CO)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-40c9ef8798c5405c862f433fe954dac4 | BrC(Br)(Br)Br.CC(C)(C)OC(=O)Nc1ccc(CO)cn1>>CC(C)(C)OC(=O)Nc1ccc(CBr)cn1 | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Br)(Br)(Br)Br.C(C)(C)(C)OC(NC1=NC=C(C=C1)CO)=O>>C(C)(C)(C)OC(NC1=NC=C(C=C1)CBr)=O | BrC(Br)(Br)[Br:14].O[CH2:13][c:12]1[cH:11][cH:10][c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[n:16][cH:15]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][Br:14])[cH:15][n:16]1 | BrC(Br)(Br)Br.CC(C)(C)OC(=O)Nc1ccc(CO)cn1 | CC(C)(C)OC(=O)Nc1ccc(CBr)cn1 | null | null | C(Cl)Cl | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | c1ccncc1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 67 | [{"value": 67.0, "product": "C(C)(C)(C)OC(NC1=NC=C(C=C1)CBr)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.5, "product": "C(C)(C)(C)OC(NC1=NC=C(C=C1)CBr)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -20 | CELSIUS | 5 | HOUR | Triphenylphosphine (8.70 g, 33.1 mmol) and carbontetrabromide (17.0 g, 51.2 mmol) were added to a suspension of (5-hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (7.00 g 31.2 mmol) in CH2Cl2 (200 mL) at room temperature. Stirring was continued for 5 h followed by evaporation of the solvent. Acetonitrile (20... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | c1ccncc1 | HBr | C(Cl)Cl | -20 | 5 | BrC(Br)(Br)Br.CC(C)(C)OC(=O)Nc1ccc(CO)cn1>C(Cl)Cl>CC(C)(C)OC(=O)Nc1ccc(CBr)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fdd178d6b86e4eb282f637ab9c2a16a5 | CC(C)(C)OC(=O)Nc1ccc(CBr)cn1.CCOC(=O)CC(=O)OCC>>CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC | C(C)(C)(C)OC(NC1=NC=C(C=C1)CBr)=O.[H-].[Na+].C(CC(=O)OCC)(=O)OCC>>C(C)OC(C(C(=O)OCC)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | Br[CH2:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][cH:21]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:22](=[O:23])[O:24][CH2:25][CH3:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH... | CC(C)(C)OC(=O)Nc1ccc(CBr)cn1.CCOC(=O)CC(=O)OCC | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC | null | null | C1CCOC1 | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | c1ccncc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15] | 44 | [{"value": 44.0, "product": "C(C)OC(C(C(=O)OCC)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.7, "product": "C(C)OC(C(C(=O)OCC)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a suspension of NaH (0.49 g, 16.3 mmol, 80%) in THF (15 mL) at 0° C. was added diethyl malonate (2.61 g, 16.3 mmol). The mixture was stirred for 15 min and was then added dropwise to a refluxed mixture of (5-bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (3.90 g, 13.6 mmol) in THF (25 mL), and the resultin... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | c1ccncc1 | HBr | C1CCOC1 | null | 0.25 | CC(C)(C)OC(=O)Nc1ccc(CBr)cn1.CCOC(=O)CC(=O)OCC>C1CCOC1>CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-dcc7ced14d924601a79f1709878a8ac1 | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC>>CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)O | [OH-].[K+].C(C)OC(C(C(=O)OCC)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O>>C(C)OC(C(C(=O)O)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | CC[O:24][C:22]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][cH:21]1)=[O:23]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][cH:... | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)O | null | null | C(Cl)Cl.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 50 | [{"value": 50.0, "product": "C(C)OC(C(C(=O)O)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.7, "product": "C(C)OC(C(C(=O)O)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of KOH (0.37 g, 6.54 mmol) in ethanol (5 mL) was added to a solution of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-malonic acid diethyl ester (2.18 g, 5.95 mmol) in ethanol (25 mL) and methylene chloride (10 mL) at 0° C. The mixture was stirred for 18 h at room temperature. The mixture was concentrate... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | Other | C(Cl)Cl.C(C)O | null | 18 | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC>C(Cl)Cl.C(C)O>CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2f8a6931a93f483288158d8ee6690ca6 | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)O>>C=C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC | C(C)NCC.O.C(C)OC(C(C(=O)O)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.C=O>>C(C)OC(C(=C)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | O=[C:1](O)[CH:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[n:16][cH:17]1)[C:18](=[O:19])[O:20][CH2:21][CH3:22]>>[CH2:1]=[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[n:16][cH:17]1)[C:18](=[O:19])[O:20][CH2:21][CH3:22... | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)O | C=C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 485594ce7bba157615ffbb01ccede84a4e638576571b5d04649a06f3d4b7bce0 | 55e5b5078322f9f4fb0a7e9b5fc8a8cb9084e9135b447b8c441ad0800765792e | c1ccncc1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3]-[c:4]:[c:5]:[#7;a:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10] | 83 | [{"value": 83.0, "product": "C(C)OC(C(=C)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.7, "product": "C(C)OC(C(=C)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Diethylamine (0.29 g, 3.00 mmol), water (2 mL) and methylene chloride (2 mL) was added to a mixture of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-malonic acid monoethyl ester (1.00 g, 2.96 mmol) and 37% aq. solution of formaldehyde (0.25 g, 3.05 mmol) at 0° C. The mixture was stirred for 16 h at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ester.Vinyl | null | null | c1ccncc1 | Other | C(Cl)Cl | null | 16 | CCOC(=O)C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)O>C(Cl)Cl>C=C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-96d8d198c68c43a1930af17b5b4a14c6 | C=C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC.CC(O)=S>>CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1 | C(C)OC(C(=C)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.C(C)N(CC)CC.C(C)(=S)O>>C(C)OC(C(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH2:7])[CH2:12][c:13]1[cH:14][cH:15][c:16]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[n:25][cH:26]1.[S:8]=[C:9]([CH3:10])[OH:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH2:12][c:13]1[cH:14][cH:15][c:16]([NH:17][C:18](=[O:1... | C=C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC.CC(O)=S | CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1 | null | null | null | Protection | OtherReaction | 56aa090d67fbecbea8a1963579cc34949775a09653b2b2f2795c609c60e70c77 | 5a9b0d631147b21b844b3c73866d1d81ab543538a176ebae28118ae7e39e572f | c1ccncc1 | [#7;a:1]:[c:2]:[c:3]-[C:4]-[C;H0;D3;+0:5](=[CH2;D1;+0:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10].[C;D1;H3:11]-[C;H0;D3;+0:12](-[OH;D1;+0:13])=[S;H0;D1;+0:14]>>[#7;a:1]:[c:2]:[c:3]-[C:4]-[CH;D3;+0:5](-[CH2;D2;+0:6]-[S;H0;D2;+0:14]-[C;H0;D3;+0:12](-[C;D1;H3:11])=[O;H0;D1;+0:13])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10] | 61 | [{"value": 61.0, "product": "C(C)OC(C(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-acrylic acid ethyl ester (0.49 g, 1.60 mmol) and triethylamine (0.17 g, 1.64 mmol) were added to thioacetic acid (3 mL) at 0° C. The mixture was stirred at room temperature for 6 h. The mixture was poured onto ice-water and extracted with CH2Cl2. The organic phase was w... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Thiocarbonyl.Vinyl | Ester.Carbo-thioester | null | null | c1ccncc1 | null | null | null | 6 | C=C(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC.CC(O)=S>>CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0f68fb696f96473182b690e0a2a91214 | CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1>>CCOC(=O)C(CSC(C)=O)Cc1ccc(N)nc1 | C(=O)(C(F)(F)F)O.C(C)OC(C(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O>>C(C)OC(C(CC=1C=NC(=CC1)N)CSC(C)=O)=O | CC(C)(C)OC(=O)[NH:17][c:16]1[cH:15][cH:14][c:13]([CH2:12][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][S:8][C:9]([CH3:10])=[O:11])[cH:19][n:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH2:12][c:13]1[cH:14][cH:15][c:16]([NH2:17])[n:18][cH:19]1 | CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1 | CCOC(=O)C(CSC(C)=O)Cc1ccc(N)nc1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5] | 141.7 | [{"value": 100.0, "product": "C(C)OC(C(CC=1C=NC(=CC1)N)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 141.7, "product": "C(C)OC(C(CC=1C=NC(=CC1)N)CSC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 60 | MINUTE | TFA (0.5 mL) was added to a solution of 2-acetylsulfanylmethyl-3-(6-tert-butoxycarbonylaminopyridin-3-yl)-propionic acid ethyl ester (100 mg, 0.26 mmol) in methylene chloride (2 mL) under argon. The solution was stirred for 60 min and concentrated under reduced pressure to give crude 2-acetylsulfanylmethyl-3-(6-amino-p... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccncc1 | HO- | C(Cl)Cl | null | 1 | CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1>C(Cl)Cl>CCOC(=O)C(CSC(C)=O)Cc1ccc(N)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c422c5c80ac74dc8a85345718451f205 | CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1>>Nc1ccc(CC(CS)C(=O)O)cn1 | C(C)OC(C(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O>>NC1=CC=C(C=N1)CC(C(=O)O)CS | CC[O:12][C:10]([CH:7]([CH2:6][c:5]1[cH:4][cH:3][c:2]([NH:1]C(=O)OC(C)(C)C)[n:14][cH:13]1)[CH2:8][S:9]C(C)=O)=[O:11]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][CH:7]([CH2:8][SH:9])[C:10](=[O:11])[OH:12])[cH:13][n:14]1 | CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1 | Nc1ccc(CC(CS)C(=O)O)cn1 | null | null | Cl | Reduction | OtherReaction | df63f36502c6e187beb1211487c3f0937031934a12a3c506c12c51a17b700a31 | 9a7c4efef36aa8beb2b85c58cd3924b350f3ef529d4eb0778d927167159d9d8b | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]-[S;H0;D2;+0:11]-C(-C)=O>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:8]=[C:7](-[OH;D1;+0:6])-[C:9]-[C:10]-[SH;D1;+0:11] | 126.1 | [{"value": 100.0, "product": "NC1=CC=C(C=N1)CC(C(=O)O)CS", "details": "PERCENTYIELD", "is_desired": false}, {"value": 126.1, "product": "NC1=CC=C(C=N1)CC(C(=O)O)CS", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | 2-Acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-propionic acid ethyl ester (38 mg, 0.096 mmol) was dissolved in conc. HCl (2.0 mL) under argon. The solution was stirred at room temperature for 1 h and then heated to reflux for 1 h. Concentration under reduced pressure gave the title compound (25.7 mg... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Carbo-thioester.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1 | HO- | Cl | null | 1 | CCOC(=O)C(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1>Cl>Nc1ccc(CC(CS)C(=O)O)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f8a92e98d3404dbf8bf128e5eee8b1de | CC(C)(C)OC(=O)Nc1ccc(CBr)cn1.CCOC(=O)C(C)C(=O)OC(C)(C)C>>CCOC(=O)C(C)(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OC(C)(C)C | CCOC(=O)C.CC(C(=O)OC(C)(C)C)C(=O)OCC.[H-].[Na+].C(C)(C)(C)OC(NC1=NC=C(C=C1)CBr)=O>>C(C)OC(C(C(=O)OC(C)(C)C)(C)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | Br[CH2:8][c:9]1[cH:10][cH:11][c:12]([NH:13][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[n:21][cH:22]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH2:8][c:9]1[cH:10][cH:11][c:12]([NH:13][C:14](=[O:15]... | CC(C)(C)OC(=O)Nc1ccc(CBr)cn1.CCOC(=O)C(C)C(=O)OC(C)(C)C | CCOC(=O)C(C)(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OC(C)(C)C | null | null | CCCCCCC.CCOC(=O)C.CN(C)C=O | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | c1ccncc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D3;+0:11](-[C;D1;H3:12])-[C:13](=[O;D1;H0:14])-[#8:15]-[C:16](-[C;D1;H3:17])(-[C;D1;H3:18])-[C;D1;H3:19]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C;H0;D4;+0:11](-[C;D1;H3:12])(-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6])-[C:13](=... | 61.5 | [{"value": 61.0, "product": "C(C)OC(C(C(=O)OC(C)(C)C)(C)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.5, "product": "C(C)OC(C(C(=O)OC(C)(C)C)(C)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | A solution of tert-butyl ethyl methylmalonate (457 mg, 2.26 mmol) in DMF (4 mL) was added dropwise to a suspension of NaH (90 mg, 2.26 mmol, 60% in oil) in DMF (4 mL). The reaction mixture was stirred for 20 min. A solution of (5-bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (500 mg, 1.74 mmol) in DMF (2.5 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | c1ccncc1 | HBr | CCCCCCC.CCOC(=O)C.CN(C)C=O | null | 0.333333 | CC(C)(C)OC(=O)Nc1ccc(CBr)cn1.CCOC(=O)C(C)C(=O)OC(C)(C)C>CCCCCCC.CCOC(=O)C.CN(C)C=O>CCOC(=O)C(C)(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b21262ed18ac45b1b012ac9c43caf368 | CCOC(=O)C(C)(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OC(C)(C)C>>CC(C)(C)OC(=O)Nc1ccc(CC(C)(C(=O)O)C(=O)OC(C)(C)C)cn1 | [OH-].[Na+].C(C)OC(C(C(=O)OC(C)(C)C)(C)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.C(Cl)Cl>>C(C)(C)(C)OC(C(C(=O)O)(C)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | CC[O:18][C:16]([C:14]([CH2:13][c:12]1[cH:11][cH:10][c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[n:27][cH:26]1)([CH3:15])[C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][C:14]([CH3:15])([C:16](=[O:1... | CCOC(=O)C(C)(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OC(C)(C)C | CC(C)(C)OC(=O)Nc1ccc(CC(C)(C(=O)O)C(=O)OC(C)(C)C)cn1 | null | null | C1CCOC1.CCO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 89 | [{"value": 89.0, "product": "C(C)(C)(C)OC(C(C(=O)O)(C)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.8, "product": "C(C)(C)(C)OC(C(C(=O)O)(C)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 16 | HOUR | 1M NaOH (2 mL) was added to a solution of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-2-methyl-malonic acid tert-butyl ester ethyl ester (0.42g, 1.03 mmol) in THF/EtOH (4 mL, 1:1) . The reaction mixture was stirred at 50° C. for 16 h. CH2Cl2 was added and the mixture was washed with 0.5 M HCl and brine and dried.... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | Other | C1CCOC1.CCO | 50 | 16 | CCOC(=O)C(C)(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OC(C)(C)C>C1CCOC1.CCO>CC(C)(C)OC(=O)Nc1ccc(CC(C)(C(=O)O)C(=O)OC(C)(C)C)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-33705ed7c39b4002b3186b0f5b799ade | CC(C)(C)OC(=O)Nc1ccc(CC(C)(C(=O)O)C(=O)OC(C)(C)C)cn1>>CC(C)(C)OC(=O)Nc1ccc(CC(C)(CO)C(=O)OC(C)(C)C)cn1 | [BH4-].[Na+].ClC(=O)OC.C(C)(C)(C)OC(C(C(=O)O)(C)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.CCN(CC)CC.Cl>>C(C)(C)(C)OC(C(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)(C)CO)=O | O=[C:16]([C:14]([CH2:13][c:12]1[cH:11][cH:10][c:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[n:26][cH:25]1)([CH3:15])[C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[OH:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][C:14]([CH3:15])([CH2:16][OH:17])[C... | CC(C)(C)OC(=O)Nc1ccc(CC(C)(C(=O)O)C(=O)OC(C)(C)C)cn1 | CC(C)(C)OC(=O)Nc1ccc(CC(C)(CO)C(=O)OC(C)(C)C)cn1 | null | null | CCOC(=O)C.C1CCOC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccncc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12]>>[C:4]-[C:3](-[C;D1;H3:5])(-[CH2;D2;+0:1]-[O;D1;H1:2])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9](-[C;D1;H3:10])(-[C;D1;H3:11])-[C;D1;H3:12] | 57 | [{"value": 57.0, "product": "C(C)(C)(C)OC(C(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)(C)CO)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.7, "product": "C(C)(C)(C)OC(C(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)(C)CO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 20 | MINUTE | Methyl chloroformate (75 μL, 0.92 mmol) was added dropwise to a solution of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-2-methyl-malonic acid mono-tert-butyl ester (348 mg, 0.915 mmol) and Et3N (123 μL, 0.92 mmol) in THF (6 mL). The reaction mixture was stirred for 20 min., filtered and added dropwise to a suspen... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccncc1 | Other | CCOC(=O)C.C1CCOC1 | null | 0.333333 | CC(C)(C)OC(=O)Nc1ccc(CC(C)(C(=O)O)C(=O)OC(C)(C)C)cn1>CCOC(=O)C.C1CCOC1>CC(C)(C)OC(=O)Nc1ccc(CC(C)(CO)C(=O)OC(C)(C)C)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e888b47742fc4305b15e5deb0b2c9806 | CC(=O)SCC(C)(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OC(C)(C)C>>CC(CS)(Cc1ccc(N)nc1)C(=O)O | C(C)(C)(C)OC(C(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)(C)CSC(C)=O)=O>>NC1=CC=C(C=N1)CC(C(=O)O)(C)CS | CC(=O)[S:4][CH2:3][C:2]([CH3:1])([CH2:5][c:6]1[cH:7][cH:8][c:9]([NH:10]C(=O)OC(C)(C)C)[n:11][cH:12]1)[C:13](=[O:14])[O:15]C(C)(C)C>>[CH3:1][C:2]([CH2:3][SH:4])([CH2:5][c:6]1[cH:7][cH:8][c:9]([NH2:10])[n:11][cH:12]1)[C:13](=[O:14])[OH:15] | CC(=O)SCC(C)(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OC(C)(C)C | CC(CS)(Cc1ccc(N)nc1)C(=O)O | null | null | Cl | Reduction | OtherReaction | a39c0c4dba61501662345cdda2d7f368bc5e8fadffcb633e88bc3f6ed0e54457 | 27913482120c0868f0c9d959294323fb2e143509e943c964b43b532c74e3e01c | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].C-C(=O)-[S;H0;D2;+0:6]-[C:7]-[C:8]-[C:9](=[O;D1;H0:10])-[O;H0;D2;+0:11]-C(-C)(-C)-C>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:10]=[C:9](-[OH;D1;+0:11])-[C:8]-[C:7]-[SH;D1;+0:6] | 100 | [{"value": 100.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Acetylsulfanylmethyl-3-(6-tert-butoxycarbonylamino-pyridin-3-yl)-2-methyl-propionic acid tert-butyl ester (4 mg, 9.4 μmol) was dissolved in conc. HCl under argon. The solution was heated to reflux for 1 h. Concentration under reduced pressure yielded the title compound as the hydrochloride salt (2.5 mg, 100%).
Condit... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Carbo-thioester.Boc.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1 | HO- | Cl | null | null | CC(=O)SCC(C)(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OC(C)(C)C>Cl>CC(CS)(Cc1ccc(N)nc1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-436afded2b2d4ff79d62622977886f08 | CC(C)(C)OC(=O)Nc1ccc(CBr)cn1.CCC1C(=O)OC(C)(C)OC1=O>>CCC1(Cc2ccc(NC(=O)OC(C)(C)C)nc2)C(=O)OC(C)(C)OC1=O | O.C(C)(C)(C)OC(NC1=NC=C(C=C1)CBr)=O.CC1(OC(C(C(O1)=O)CC)=O)C.C(C)N(CC)CC>>C(C)(C)(C)OC(NC1=NC=C(C=C1)CC1(C(OC(OC1=O)(C)C)=O)CC)=O | Br[CH2:4][c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[n:17][cH:18]1.[CH3:1][CH2:2][CH:3]1[C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[O:25][C:26]1=[O:27]>>[CH3:1][CH2:2][C:3]1([CH2:4][c:5]2[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[n:17]... | CC(C)(C)OC(=O)Nc1ccc(CBr)cn1.CCC1C(=O)OC(C)(C)OC1=O | CCC1(Cc2ccc(NC(=O)OC(C)(C)C)nc2)C(=O)OC(C)(C)OC1=O | null | null | CS(=O)C | C-C Coupling | OtherReaction | 58c01b66b8fc3a6ba5c7ea5eb9ff9622f5543ddf5dc16015d0c2c6736b592a81 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | O=C1OCOC(=O)C1Cc1cccnc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[C;D1;H3:7]-[C:8]-[CH;D3;+0:9]1-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]-[#8:14]-[C:15]-1=[O;D1;H0:16]>>[C;D1;H3:7]-[C:8]-[C;H0;D4;+0:9]1(-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]-[#8:14]-[C:15]-1=[O;D1;H0:16] | 87.3 | [{"value": 87.0, "product": "C(C)(C)(C)OC(NC1=NC=C(C=C1)CC1(C(OC(OC1=O)(C)C)=O)CC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.3, "product": "C(C)(C)(C)OC(NC1=NC=C(C=C1)CC1(C(OC(OC1=O)(C)C)=O)CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (5-Bromomethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (1.0 g, 3.48 mmol) was added to a solution of 2,2-dimethyl-5-ethyl-1,3-dioxane4,6-dione (600 mg, 3.48 mmol) and triethylamine (0.51 mL, 3.66 mmol) in dimethyl sulfoxide (40 mL) under nitrogen. The reaction mixture was stirred over night and water (100 mL) was ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | C1COCOC1 | C1COCOC1 | c1ccncc1.C1COCOC1 | HBr | CS(=O)C | null | null | CC(C)(C)OC(=O)Nc1ccc(CBr)cn1.CCC1C(=O)OC(C)(C)OC1=O>CS(=O)C>CCC1(Cc2ccc(NC(=O)OC(C)(C)C)nc2)C(=O)OC(C)(C)OC1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eecf4b8b12244c0d82a0c50d09c6c711 | CCOC(=O)C(CC)(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)O>>CCOC(=O)C(CC)(CO)Cc1ccc(NC(=O)OC(C)(C)C)nc1 | [BH4-].[Na+].ClC(=O)OC.C(C)OC(C(C(=O)O)(CC)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.CCN(CC)CC.Cl>>C(C)OC(C(CC)(CO)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | O=[C:9]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH2:7][CH3:8])[CH2:11][c:12]1[cH:13][cH:14][c:15]([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[n:24][cH:25]1)[OH:10]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH2:7][CH3:8])([CH2:9][OH:10])[CH2:11][c:12]1[cH:13][cH:14][c:15]([NH:16][C:17](=[O:18])[O:19][... | CCOC(=O)C(CC)(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)O | CCOC(=O)C(CC)(CO)Cc1ccc(NC(=O)OC(C)(C)C)nc1 | null | null | C(Cl)Cl.C1CCOC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccncc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3](-[C:4])(-[C:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]>>[C:4]-[C:3](-[C:5])(-[CH2;D2;+0:1]-[O;D1;H1:2])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9] | 45 | [{"value": 45.0, "product": "C(C)OC(C(CC)(CO)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 44.6, "product": "C(C)OC(C(CC)(CO)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 50 | MINUTE | Methyl chloroformate (150 pL, 1.95 mmol) was added dropwise to a solution of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-2-ethyl-malonic acid monoethyl ester (700 mg, 1.91 mmol) and Et3N (275 μL, 1.97 mmol) in THF (15 mL) at −20° C. under nitrogen. The reaction mixture was stirred for 50 min., filtered and added ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccncc1 | Other | C(Cl)Cl.C1CCOC1 | null | 0.833333 | CCOC(=O)C(CC)(Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)O>C(Cl)Cl.C1CCOC1>CCOC(=O)C(CC)(CO)Cc1ccc(NC(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c7bfad46cf2d45ad9426ac70adf14b9c | CCOC(=O)C(CC)(CO)Cc1ccc(NC(=O)OC(C)(C)C)nc1.O=C(O)Cc1cccs1>>CCOC(=O)C(CC)(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1 | N(=NC(=O)OC(C)C)C(=O)OC(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.S1C(=CC=C1)CC(=O)O.C(C)OC(C(CC)(CO)CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O>>C(C)OC(C(CC)(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O | O[CH2:9][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH2:7][CH3:8])[CH2:14][c:15]1[cH:16][cH:17][c:18]([NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[n:27][cH:28]1.OC([CH2:12][c:11]1ccc[s:10]1)=[O:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH2:7][CH3:8])([CH2:9][S:10][C:11]([CH3:12])=[O:13])[CH2:14][c:15]... | CCOC(=O)C(CC)(CO)Cc1ccc(NC(=O)OC(C)(C)C)nc1.O=C(O)Cc1cccs1 | CCOC(=O)C(CC)(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1 | null | null | C1CCOC1 | Protection | OtherReaction | 189263d4d19565b9c5c001a81e8abf2a60b1807919ec489920cd4293a1993653 | 7a83c40990eef465e85ff66652874583517e7c7b69d7750d5f2438fef535f94e | c1ccncc1 | O-C(=[O;H0;D1;+0:1])-[CH2;D2;+0:2]-[c;H0;D3;+0:3]1:[s;H0;D2;+0:4]:c:c:c:1.O-[CH2;D2;+0:5]-[C:6](-[C:7])(-[C:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]>>[C:7]-[C:6](-[C:8])(-[CH2;D2;+0:5]-[S;H0;D2;+0:4]-[C;H0;D3;+0:3](-[CH3;D1;+0:2])=[O;H0;D1;+0:1])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12] | 61.1 | [{"value": 61.0, "product": "C(C)OC(C(CC)(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.1, "product": "C(C)OC(C(CC)(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Diisopropyl azodicarboxylate (296 μL, 1.53 mmol) was added dropwise to a solution of triphenylphosphine (402 mg, 1.53 mmol) in THF (4 mL) at 0° C. under argon and the reaction was stirred for 30 min. A solution of thiolacetic acid (109 μL, 1.53 mmol) and 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-2-hydroxymethyl... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Carbo-thioester | c1ccsc1 | null | c1ccncc1 | HO- | C1CCOC1 | null | 0.5 | CCOC(=O)C(CC)(CO)Cc1ccc(NC(=O)OC(C)(C)C)nc1.O=C(O)Cc1cccs1>C1CCOC1>CCOC(=O)C(CC)(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cfa2598c674d45cd8384f953ab1e1107 | CCOC(=O)C(CC)(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1>>CCC(CS)(Cc1ccc(N)nc1)C(=O)O | C(C)OC(C(CC)(CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)CSC(C)=O)=O>>NC1=CC=C(C=N1)CC(C(=O)O)(CC)CS | CC[O:16][C:14]([C:3]([CH2:2][CH3:1])([CH2:4][S:5]C(C)=O)[CH2:6][c:7]1[cH:8][cH:9][c:10]([NH:11]C(=O)OC(C)(C)C)[n:12][cH:13]1)=[O:15]>>[CH3:1][CH2:2][C:3]([CH2:4][SH:5])([CH2:6][c:7]1[cH:8][cH:9][c:10]([NH2:11])[n:12][cH:13]1)[C:14](=[O:15])[OH:16] | CCOC(=O)C(CC)(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1 | CCC(CS)(Cc1ccc(N)nc1)C(=O)O | null | null | Cl | Reduction | OtherReaction | df63f36502c6e187beb1211487c3f0937031934a12a3c506c12c51a17b700a31 | 9a7c4efef36aa8beb2b85c58cd3924b350f3ef529d4eb0778d927167159d9d8b | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]-[S;H0;D2;+0:11]-C(-C)=O>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:8]=[C:7](-[OH;D1;+0:6])-[C:9]-[C:10]-[SH;D1;+0:11] | 100 | [{"value": 100.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Acetylsulfanylmethyl-2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-butyric acid ethyl ester (12.3 mg, 30 μmol) was dissolved in conc. HCl (2 mL) under argon. The solution was heated to reflux for 24 h. Concentration under reduced pressure gave the title compound as the hydrochloride salt (8.3 mg, 100%).
Condition... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ester.Ether.Carbo-thioester.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1 | HO- | Cl | null | null | CCOC(=O)C(CC)(CSC(C)=O)Cc1ccc(NC(=O)OC(C)(C)C)nc1>Cl>CCC(CS)(Cc1ccc(N)nc1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9eb117af31054614bd2029b09386dfab | CC1C(=O)OC(C)(C)OC1=O.Cc1cc(CBr)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>Cc1cc(CC2(C)C(=O)OC(C)(C)OC2=O)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | O.C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=C1C)CBr.CC1(OC(C(C(O1)=O)C)=O)C.C(C)N(CC)CC>>C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=C1C)CC1(C(OC(OC1=O)(C)C)=O)C | [CH:6]1([CH3:7])[C:8](=[O:9])[O:10][C:11]([CH3:12])([CH3:13])[O:14][C:15]1=[O:16].Br[CH2:5][c:4]1[cH:3][c:2]([CH3:1])[c:19]([N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[C:28](=[O:29])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])[n:18][cH:17]1>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][C:6]2([CH3:7])[C:8](=[O:9])[... | CC1C(=O)OC(C)(C)OC1=O.Cc1cc(CBr)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | Cc1cc(CC2(C)C(=O)OC(C)(C)OC2=O)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | null | null | CS(=O)C | C-C Coupling | OtherReaction | 58c01b66b8fc3a6ba5c7ea5eb9ff9622f5543ddf5dc16015d0c2c6736b592a81 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | O=C1OCOC(=O)C1Cc1cccnc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[C;D1;H3:7]-[CH;D3;+0:8]1-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]-[#8:13]-[C:14]-1=[O;D1;H0:15]>>[C;D1;H3:7]-[C;H0;D4;+0:8]1(-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]-[#8:13]-[C:14]-1=[O;D1;H0:15] | 107.6 | [{"value": 107.6, "product": "C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=C1C)CC1(C(OC(OC1=O)(C)C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 2-[N,N-bis(tert-Butoxycarbonyl)amino]-5-bromomethyl-3-methyl-pyridin (1.6 g, 4.0 mmol) was added to a solution of 2,2,5-trimethyl-1,3-dioxane-4,6-dione (630 mg, 4.0 mmol) and triethylamine (0.58 mL, 4.2 mmol) in dimethyl sulfoxide (40 mL). The reaction mixture was stirred overnight and water (100 mL) was added. The mix... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | C1COCOC1 | C1COCOC1 | c1ccncc1.C1COCOC1 | HBr | CS(=O)C | null | 8 | CC1C(=O)OC(C)(C)OC1=O.Cc1cc(CBr)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>CS(=O)C>Cc1cc(CC2(C)C(=O)OC(C)(C)OC2=O)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-959be78dd6ce41cfb97af2d09627fb54 | Cc1cc(CC2(C)C(=O)OC(C)(C)OC2=O)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>CCOC(=O)C(C)(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)O | [Na].C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=C1C)CC1(C(OC(OC1=O)(C)C)=O)C.C(Cl)Cl>>C(C)OC(C(C(=O)O)(C)CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O | CC1([CH3:1])[O:3][C:4](=[O:5])[C:6]([CH3:7])([CH2:8][c:9]2[cH:10][n:11][c:12]([N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[c:28]([CH3:29])[cH:30]2)[C:31](=[O:32])[O:33]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH2:8][c:9]1[cH:10][n:11][... | Cc1cc(CC2(C)C(=O)OC(C)(C)OC2=O)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | CCOC(=O)C(C)(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)O | null | null | C(C)O | Miscellaneous | OtherReaction | 63ad813d1b77dce0fe5208aa14f611372b0920cdb45ff078385c4a27a0c20f9d | aec9bcb7276f5cbf55cd2b59ffe4fcb8e927c2173953b25a21ea57417487cdf3 | c1ccncc1 | C-C1(-[CH3;D1;+0:1])-[O;H0;D2;+0:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6](=[O;D1;H0:7])-[O;H0;D2;+0:8]-1>>[CH3;D1;+0:1]-[C:9]-[O;H0;D2;+0:8]-[C:6](=[O;D1;H0:7])-[C:5]-[C:3](=[O;D1;H0:4])-[OH;D1;+0:2] | 101.8 | [{"value": 101.8, "product": "C(C)OC(C(C(=O)O)(C)CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 60 | MINUTE | A solution of sodium metal (184 mg, 8.0 mmol) in ethanol (20 mL) was added to a solution of crude 2-[N,N-bis(tert-butoxycarbonyl)amino]-3-methyl-5-(2,2,5-trimethyl-4,6-dioxo-[1,3]dioxan-5-ylmethyl)-pyridin (2.06 g, ˜4.0 mmol) in ethanol (20 mL) under argon. The reaction was stirred for 60 min. and methylene chloride wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Carboxylic acid.Ester | C1COCOC1 | null | c1ccncc1 | Other | C(C)O | null | 1 | Cc1cc(CC2(C)C(=O)OC(C)(C)OC2=O)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>C(C)O>CCOC(=O)C(C)(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b2cf4b90866342179f06cdfb89ca06a9 | CCOC(=O)C(C)(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)O>>CCOC(=O)C(C)(CO)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1 | [BH4-].[Na+].ClC(=O)OC.C(C)OC(C(C(=O)O)(C)CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O.CCN(CC)CC.Cl>>C(C)OC(C(CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)(C)CO)=O | O=[C:8]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH2:10][c:11]1[cH:12][n:13][c:14]([N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[c:30]([CH3:31])[cH:32]1)[OH:9]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH2:8][OH:9])[CH2:10][c:11]1[... | CCOC(=O)C(C)(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)O | CCOC(=O)C(C)(CO)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1 | null | null | C(Cl)Cl.C1CCOC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccncc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9]>>[C:4]-[C:3](-[C;D1;H3:5])(-[CH2;D2;+0:1]-[O;D1;H1:2])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9] | 49 | [{"value": 49.0, "product": "C(C)OC(C(CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)(C)CO)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.0, "product": "C(C)OC(C(CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)(C)CO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 50 | MINUTE | Methyl chloroformate (338 μL, 4.4 mmol) was added dropwise to a solution of crude 2-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-yl methyl)-2-methyl-malonic acid monoethyl ester (1.9 g) and Et3N (641 μL, 4.6 mmol) in THF (30 mL) at −20° C. The reaction mixture was stirred for 50 min., filtered and added dr... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccncc1 | Other | C(Cl)Cl.C1CCOC1 | null | 0.833333 | CCOC(=O)C(C)(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)O>C(Cl)Cl.C1CCOC1>CCOC(=O)C(C)(CO)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-aa19bb171de64621a59f5aa38227aad1 | CCOC(=O)C(C)(CO)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1.O=C(O)Cc1cccs1>>CCOC(=O)C(C)(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1 | N(=NC(=O)OC(C)C)C(=O)OC(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.S1C(=CC=C1)CC(=O)O.C(C)OC(C(CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)(C)CO)=O>>C(C)OC(C(CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)(C)CSC(C)=O)=O | O[CH2:8][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH2:13][c:14]1[cH:15][n:16][c:17]([N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[C:26](=[O:27])[O:28][C:29]([CH3:30])([CH3:31])[CH3:32])[c:33]([CH3:34])[cH:35]1.OC([CH2:11][c:10]1ccc[s:9]1)=[O:12]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([... | CCOC(=O)C(C)(CO)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1.O=C(O)Cc1cccs1 | CCOC(=O)C(C)(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1 | null | null | C1CCOC1 | Protection | OtherReaction | 189263d4d19565b9c5c001a81e8abf2a60b1807919ec489920cd4293a1993653 | 7a83c40990eef465e85ff66652874583517e7c7b69d7750d5f2438fef535f94e | c1ccncc1 | O-C(=[O;H0;D1;+0:1])-[CH2;D2;+0:2]-[c;H0;D3;+0:3]1:[s;H0;D2;+0:4]:c:c:c:1.O-[CH2;D2;+0:5]-[C:6](-[C:7])(-[C;D1;H3:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12]>>[C:7]-[C:6](-[C;D1;H3:8])(-[CH2;D2;+0:5]-[S;H0;D2;+0:4]-[C;H0;D3;+0:3](-[CH3;D1;+0:2])=[O;H0;D1;+0:1])-[C:9](=[O;D1;H0:10])-[#8:11]-[C:12] | 145.9 | [{"value": 145.9, "product": "C(C)OC(C(CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)(C)CSC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | Diisopropyl azodicarboxylate (755 μL, 3.91 mmol) was added dropwise to a solution of triphenylphosphine (1.026 g, 3.91 mmol) in THF (10 mL) at 0° C. and the reaction was stirred for 30 min. A solution of thiolacetic acid (279 μL, 3.91 mmol) and 3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-yl)-2-hydroxyme... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary alcohol | Carbo-thioester | c1ccsc1 | null | c1ccncc1 | HO- | C1CCOC1 | null | 0.5 | CCOC(=O)C(C)(CO)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1.O=C(O)Cc1cccs1>C1CCOC1>CCOC(=O)C(C)(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0b8e6143433749e2944677c438c6313f | CCOC(=O)C(C)(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1>>CCOC(=O)C(C)(CSC(C)=O)Cc1cnc(N)c(C)c1 | C(C)OC(C(CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)(C)CSC(C)=O)=O>>C(C)OC(C(CC=1C=NC(=C(C1)C)N)(C)CSC(C)=O)=O | CC(C)(C)OC(=O)[N:18](C(=O)OC(C)(C)C)[c:17]1[n:16][cH:15][c:14]([CH2:13][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH2:8][S:9][C:10]([CH3:11])=[O:12])[cH:21][c:19]1[CH3:20]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH2:8][S:9][C:10]([CH3:11])=[O:12])[CH2:13][c:14]1[cH:15][n:16][c:17]([NH2:18])[c:19]([CH3:20... | CCOC(=O)C(C)(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1 | CCOC(=O)C(C)(CSC(C)=O)Cc1cnc(N)c(C)c1 | null | null | C(=O)(C(F)(F)F)O | Reduction | Boc amine deprotection | f552418eb10f74be275b3d2d2e4940118153e34a0e9e4737d38c7264f73cdda0 | c2e7125d1a630bb54d8f171aedbfa925f5104f1c1e5ac8c4ed9643a0c1117a44 | c1ccncc1 | 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] | 84 | [{"value": 84.0, "product": "C(C)OC(C(CC=1C=NC(=C(C1)C)N)(C)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.4, "product": "C(C)OC(C(CC=1C=NC(=C(C1)C)N)(C)CSC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 60 | MINUTE | Crude 2-acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-yl)-2-methyl-propionic acid ethyl ester (1.46 g) was dissolved in TFA (5 mL) and stirred for 60 min. Concentration under reduced pressure followed by chromathography (toluene/EtOAc, 1:1→1:10→0:1) gave slightly impure 2-acetylsulfan... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ether.Ether.Substituted dicarboximide.Boc.Boc | Primary amine | null | null | c1ccncc1 | HO- | C(=O)(C(F)(F)F)O | null | 1 | CCOC(=O)C(C)(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1>C(=O)(C(F)(F)F)O>CCOC(=O)C(C)(CSC(C)=O)Cc1cnc(N)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b962369971ea4d278e8a5ef08961e63a | CCOC(=O)C(C)(CSC(C)=O)Cc1cnc(N)c(C)c1>>Cc1cc(CC(C)(CS)C(=O)O)cnc1N | C(C)OC(C(CC=1C=NC(=C(C1)C)N)(C)CSC(C)=O)=O>>NC1=C(C=C(C=N1)CC(C(=O)O)(C)CS)C | CC[O:12][C:10]([C:6]([CH2:5][c:4]1[cH:3][c:2]([CH3:1])[c:15]([NH2:16])[n:14][cH:13]1)([CH3:7])[CH2:8][S:9]C(C)=O)=[O:11]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][C:6]([CH3:7])([CH2:8][SH:9])[C:10](=[O:11])[OH:12])[cH:13][n:14][c:15]1[NH2:16] | CCOC(=O)C(C)(CSC(C)=O)Cc1cnc(N)c(C)c1 | Cc1cc(CC(C)(CS)C(=O)O)cnc1N | null | null | Cl | Reduction | OtherReaction | 1bcd8cbb2f136b4bcba1690e9ba45c4e43c89ba76f0e22de82a7d3fe318c82a9 | 5654c46fe4cb226f88ec3c899c7f9be1825c357673ea686958f9ef4883ee1db3 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[S;H0;D2;+0:6]-C(-C)=O>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[C:4]-[C:5]-[SH;D1;+0:6] | 96 | [{"value": 96.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Acetylsulfanylmethyl-3-(6-amino-5-methyl-pyridin-3-yl)-2-methyl-propionic acid ethyl ester (17 mg, 40 μmol) was dissolved in conc. HCl (2 mL) under argon. The solution was heated to reflux for 150 min. Concentration under reduced pressure gave the title compound as the hydrochloride salt (10.7 mg, 96%).
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Carbo-thioester | Carboxylic acid.Aliphatic thiol | null | null | c1ccncc1 | HO- | Cl | null | null | CCOC(=O)C(C)(CSC(C)=O)Cc1cnc(N)c(C)c1>Cl>Cc1cc(CC(C)(CS)C(=O)O)cnc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-36d991e903c24644903420e72332da4d | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]O[Si](C)(C)C(C)(C)C.Cc1cc(Br)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>Cc1cc(C(C)(C)O[SiH2]C(C)(C)C)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | [F-].[K+].BrC=1C=C(C(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C.C(C)(C)(C)[Si](OC[Sn](CCCC)(CCCC)CCCC)(C)C.ClCCCl.C(C)OCC>>C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=C1C)C(O[SiH2]C(C)(C)C)(C)C | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2:5][O:8][Si:9]([CH3:6])([CH3:7])[C:10]([CH3:11])([CH3:12])[CH3:13].Br[c:4]1[cH:3][c:2]([CH3:1])[c:16]([N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[n:15][cH:14]1>>[CH3:1][c:2]1[cH:3][c:4]([C:5]([CH3:6])([CH3:7]... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]O[Si](C)(C)C(C)(C)C.Cc1cc(Br)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | Cc1cc(C(C)(C)O[SiH2]C(C)(C)C)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | null | C-C Coupling | OtherReaction | 2c35ffcca42587548be5417494593198fc16ef4537fcb3507e56ecb0940f483d | e19d215278fe89455f513eea1f431a9cbd352fd26641180be69d9777a377b4b5 | c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1.C-C-C-[CH2]-[Sn](-[CH2;D2;+0:7]-[#8:8]-[Si;H0;D4;+0:9](-[CH3;D1;+0:10])(-[CH3;D1;+0:11])-[C:12](-[C;D1;H3:13])(-[C;D1;H3:14])-[C;D1;H3:15])(-[CH2]-C-C-C)-[CH2]-C-C-C>>[C;D1;H3:13]-[C:12](-[C;D1;H3:14])(-[C;D1;H3:15])-[SiH2;D2;+0:9]-[#8:8]-[C;H0;D4;+0:7](-[CH3;D1;+0:... | 59 | [{"value": 59.0, "product": "C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=C1C)C(O[SiH2]C(C)(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | A solution of 5-bromo-2-[N,N-bis(tert-butoxycarbonyl)amino]-3-methyl-pyridin (26.0 g, 67.1 mmol), tert-butyl-dimethyl-tributylstannanylmethoxy-silane (47.6 g, 109 mmol), and bis(triphenylphosphine)palladium(II) dichloride (0.90 g, 1.42 mmol) in 1,2-dichloroethane (80 mL) was stirred at 90° C. for two days. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.TMS ether protective group.Tin | null | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr.Sn | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | 0 | 0.5 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]O[Si](C)(C)C(C)(C)C.Cc1cc(Br)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl>Cc1cc(C(C)(C)O[SiH2]C(C)(C)C)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7f016dac5a71499cab1442bd665fa2a5 | Cc1cc(C(C)(C)O[SiH2]C(C)(C)C)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>Cc1cc(CO)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=C1C)C(O[SiH2]C(C)(C)C)(C)C>>C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=C1C)CO | CC(C)(C)[SiH2][O:6][C:5](C)(C)[c:4]1[cH:3][c:2]([CH3:1])[c:9]([N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[n:8][cH:7]1>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][OH:6])[cH:7][n:8][c:9]1[N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[C:18]... | Cc1cc(C(C)(C)O[SiH2]C(C)(C)C)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | Cc1cc(CO)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | null | null | C1CCOC1 | Deprotection | OtherReaction | d7487e9652d81f9226fa8fb90bf02725deb1441d4abc97ee4fdbe439e00122e0 | ff9889ffd40f59bd281424811967f384d29acb01a2d54e10590c5a677f81d17a | c1ccncc1 | C-C(-C)(-C)-[SiH2]-[O;H0;D2;+0:1]-[C;H0;D4;+0:2](-C)(-C)-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 59.4 | [{"value": 59.0, "product": "C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=C1C)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.4, "product": "C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=C1C)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Tetrabutylammonium fluoride (25.1 g 79.6 mmol) was added to a solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-methylpyridin (18.0 g, 39.8 mmol) in THF (150 mL). The reaction mixture was stirred overnight at room temperature. Concentration under reduced pressure followed by f... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | null | null | c1ccncc1 | Other | C1CCOC1 | null | 8 | Cc1cc(C(C)(C)O[SiH2]C(C)(C)C)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>C1CCOC1>Cc1cc(CO)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-56843a12b02b48b19d22edc5fd10549e | BrC(Br)(Br)Br.Cc1cc(CO)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>Cc1cc(CBr)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Br)(Br)(Br)Br.C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=C1C)CO>>BrCC=1C=C(C(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C | BrC(Br)(Br)[Br:6].O[CH2:5][c:4]1[cH:3][c:2]([CH3:1])[c:9]([N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[n:8][cH:7]1>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][Br:6])[cH:7][n:8][c:9]1[N:10]([C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[C:18](=[O... | BrC(Br)(Br)Br.Cc1cc(CO)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | Cc1cc(CBr)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | null | null | ClCCl | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | c1ccncc1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 84.5 | [{"value": 77.0, "product": "BrCC=1C=C(C(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.5, "product": "BrCC=1C=C(C(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Triphenylphosphine (7.43 g, 28.3 mmol) and CBr4 (9.49 g, 28.6 mmol) was added to a solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-3-methylpyridin (8.00 g, 23.6 mmol) in dichloromethane (220 mL) at 0° C. The reaction mixture was stirred for 3 h and was then concentrated under reduced pressure. Flash c... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | c1ccncc1 | HBr | ClCCl | null | 3 | BrC(Br)(Br)Br.Cc1cc(CO)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>ClCCl>Cc1cc(CBr)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bae3f117e03c4bedae6115f447a87479 | CCOC(=O)CC(=O)OCC.Cc1cc(CBr)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)OCC | C(C)(=O)OCC.C(CC(=O)OCC)(=O)OCC.[H-].[Na+].C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C=C1C)CBr>>C(C)OC(C(C(=O)OCC)CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:30](=[O:31])[O:32][CH2:33][CH3:34].Br[CH2:7][c:8]1[cH:9][n:10][c:11]([N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[c:27]([CH3:28])[cH:29]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10]... | CCOC(=O)CC(=O)OCC.Cc1cc(CBr)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)OCC | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | c1ccncc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15] | 50 | [{"value": 50.0, "product": "C(C)OC(C(C(=O)OCC)CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 49.9, "product": "C(C)OC(C(C(=O)OCC)CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a suspension of NaH (0.24 g, 6.0 mmol, 60%) in DMF (5 mL) was added diethyl malonate (0.91 mL, 6.0 mmol) and the mixture was stirred for 15 min. A solution 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-bromomethyl-3-methyl-pyridin (2.0 g, 5.0 mmol) in DMF (5 mL) was added and the resulting solution stirred for 120 min at ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | c1ccncc1 | HBr | CN(C)C=O | null | 0.25 | CCOC(=O)CC(=O)OCC.Cc1cc(CBr)cnc1N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>CN(C)C=O>CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e3ec7f046bc24f2f8fdc07ad0f018346 | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)OCC>>CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)O | [OH-].[K+].C(C)OC(C(C(=O)OCC)CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O>>C(C)OC(C(C(=O)O)CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O | CC[O:32][C:30]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][c:8]1[cH:9][n:10][c:11]([N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[c:27]([CH3:28])[cH:29]1)=[O:31]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10][c:11]([N:12]([C... | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)OCC | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)O | null | null | C(Cl)Cl.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 88.4 | [{"value": 88.0, "product": "C(C)OC(C(C(=O)O)CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.4, "product": "C(C)OC(C(C(=O)O)CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of KOH (154 mg, 2.75 mmol) in ethanol (2 mL) was added to a solution 2-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-ylmethyl)-malonic acid diethyl ester (1.2 g, 2.50 mmol) in ethanol (10 mL) and methylene chloride (4 mL) at 0° C. The mixture was stirred for 18 h at room temperature. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | Other | C(Cl)Cl.C(C)O | null | 18 | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)OCC>C(Cl)Cl.C(C)O>CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f93ca83672634c3ca17565cf8c3f0b67 | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)O>>C=C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)OCC | C(C)NCC.C(C)OC(C(C(=O)O)CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O.C=O.C(C)(=O)OCC>>C(C)OC(C(=C)CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O | O=[C:1](O)[CH:2]([CH2:3][c:4]1[cH:5][n:6][c:7]([N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[c:23]([CH3:24])[cH:25]1)[C:26](=[O:27])[O:28][CH2:29][CH3:30]>>[CH2:1]=[C:2]([CH2:3][c:4]1[cH:5][n:6][c:7]([N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:... | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)O | C=C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)OCC | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 485594ce7bba157615ffbb01ccede84a4e638576571b5d04649a06f3d4b7bce0 | 55e5b5078322f9f4fb0a7e9b5fc8a8cb9084e9135b447b8c441ad0800765792e | c1ccncc1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3]-[c:4]:[c:5]:[#7;a:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10] | 73.5 | [{"value": 73.0, "product": "C(C)OC(C(=C)CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.5, "product": "C(C)OC(C(=C)CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Diethylamine (0.26 g, 2.67 mmol) was added a mixture of 2-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-ylmethyl)-malonic acid monoethyl ester (1.0 g, 2.2 mmol) and 37% aq. solution of formaldehyde (0.24 g, 3.00 mmol) in methylene chloride (2 mL) at 0° C. The mixture was stirred for 16 h at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ester.Vinyl | null | null | c1ccncc1 | Other | C(Cl)Cl | null | 16 | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)O>C(Cl)Cl>C=C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3a1653c40d78486e965a2443fb236cdc | C=C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)OCC.CC(O)=S>>CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1 | C(C)N(CC)CC.C(C)OC(C(=C)CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O.C(C)(=S)O.C(C)(=O)OCC>>C(C)OC(C(CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)CSC(C)=O)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH2:7])[CH2:12][c:13]1[cH:14][n:15][c:16]([N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[c:32]([CH3:33])[cH:34]1.[S:8]=[C:9]([CH3:10])[OH:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10... | C=C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)OCC.CC(O)=S | CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1 | null | null | null | Protection | OtherReaction | 56aa090d67fbecbea8a1963579cc34949775a09653b2b2f2795c609c60e70c77 | 5a9b0d631147b21b844b3c73866d1d81ab543538a176ebae28118ae7e39e572f | c1ccncc1 | [#7;a:1]:[c:2]:[c:3]-[C:4]-[C;H0;D3;+0:5](=[CH2;D1;+0:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10].[C;D1;H3:11]-[C;H0;D3;+0:12](-[OH;D1;+0:13])=[S;H0;D1;+0:14]>>[#7;a:1]:[c:2]:[c:3]-[C:4]-[CH;D3;+0:5](-[CH2;D2;+0:6]-[S;H0;D2;+0:14]-[C;H0;D3;+0:12](-[C;D1;H3:11])=[O;H0;D1;+0:13])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10] | 43 | [{"value": 43.0, "product": "C(C)OC(C(CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Triethylamine (0.234 mL, 1.68 mmol) was added to a solution of 2-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-ylmethyl)-acrylic acid ethyl ester (0.68 g, 1.61 mmol) in thioacetic acid (3 mL) at 0° C. The mixture was stirred at room temperature for 16 h. Ethyl acetate was added and the organic phase was was... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Thiocarbonyl.Vinyl | Ester.Carbo-thioester | null | null | c1ccncc1 | null | null | null | 16 | C=C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1)C(=O)OCC.CC(O)=S>>CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-03fea22a728046a797595b16b44adb1c | CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1>>Cc1cc(CC(CS)C(=O)O)cnc1N | C(C)OC(C(CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)CSC(C)=O)=O>>NC1=C(C=C(C=N1)CC(C(=O)O)CS)C | CC[O:11][C:9]([CH:6]([CH2:5][c:4]1[cH:3][c:2]([CH3:1])[c:14]([N:15](C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)[n:13][cH:12]1)[CH2:7][S:8]C(C)=O)=[O:10]>>[CH3:1][c:2]1[cH:3][c:4]([CH2:5][CH:6]([CH2:7][SH:8])[C:9](=[O:10])[OH:11])[cH:12][n:13][c:14]1[NH2:15] | CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1 | Cc1cc(CC(CS)C(=O)O)cnc1N | null | null | Cl | Reduction | OtherReaction | ff200d63748925ecb928aee95d999f108474ef3634c58d22fe1e9be9ac805fa3 | 430680ed2de5eb87de586bf5706158a5dd503c4be3ff91566980452c5549779b | c1ccncc1 | 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].C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]-[S;H0;D2;+0:11]-C(-C)=O>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:8]=[C:7](-[OH;D1;+0:6])-[C:9]-[C:10]-[SH;D1;+0:11] | 115.7 | [{"value": 100.0, "product": "NC1=C(C=C(C=N1)CC(C(=O)O)CS)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 115.7, "product": "NC1=C(C=C(C=N1)CC(C(=O)O)CS)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-yl)-propionic acid ethyl ester (17 mg, 0.034 mmol) was dissolved in conc. HCl (3.0 mL). The solution was heated to reflux for 1 h. Concentration under reduced pressure gave the title compound (8.9 mg, 100%) as the hydrochloride salt.
Con... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ester.Ether.Ether.Substituted dicarboximide.Carbo-thioester.Boc.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1 | HO- | Cl | null | null | CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1>Cl>Cc1cc(CC(CS)C(=O)O)cnc1N |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9c5095105cfe4857aa00178cf8638848 | Br.Cc1ccnc(N)c1>>Cc1cc(N)ncc1Br | NC1=NC=CC(=C1)C.Br.OO.C([O-])([O-])=O.[Na+].[Na+]>>NC1=NC=C(C(=C1)C)Br | [BrH:9].[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:6][cH:7][cH:8]1>>[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:6][cH:7][c:8]1[Br:9] | Br.Cc1ccnc(N)c1 | Cc1cc(N)ncc1Br | null | null | null | Functional Group Addition | Bromination | 7c108e53aa6849672ac0ea1998cfd24df7835b0d1bc5738d16f4d561a472c88e | 0a2f22058f27970cef4a98a778644dbe9c44e91f66c74cd24db321993177608a | c1ccncc1 | [BrH;D0;+0:1].[C;D1;H3:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[c:7]:[cH;D2;+0:8]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:8]1:[c:7]:[#7;a:6]:[c:5]:[c:4]:[c:3]:1-[C;D1;H3:2] | 40 | [{"value": 40.0, "product": "NC1=NC=C(C(=C1)C)Br", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 90 | MINUTE | 2-Amino-4-methylpyridine (110 g, 1.02 mol) in hydrobromic acid (1 L, 48%) was stirred at 70° C. and a solution of hydrogen peroxide (300 mL, 15%) was added dropwise over a one h at such a rate that the temperature of the reaction mixture remained at 70-80° C. The mixture was stirred for 90 min at 70° C. and poured onto... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccncc1 | c1ccncc1 | c1ccncc1 | null | null | 70 | 1.5 | Br.Cc1ccnc(N)c1>>Cc1cc(N)ncc1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-11b564af92244385904b20e883187645 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]O[Si](C)(C)C(C)(C)C.Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1Br>>Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1C(C)(C)O[SiH2]C(C)(C)C | [F-].[K+].C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C(=C1)C)Br.C(C)(C)(C)[Si](OC[Sn](CCCC)(CCCC)CCCC)(C)C.ClCCCl.C(C)OCC>>C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C(=C1)C)C(O[SiH2]C(C)(C)C)(C)C | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2:23][O:26][Si:27]([CH3:24])([CH3:25])[C:28]([CH3:29])([CH3:30])[CH3:31].Br[c:22]1[c:2]([CH3:1])[cH:3][c:4]([N:5]([C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][cH:21]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]([C:6](=[O:7])[O:... | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]O[Si](C)(C)C(C)(C)C.Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1Br | Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1C(C)(C)O[SiH2]C(C)(C)C | null | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | null | C-C Coupling | OtherReaction | 2c35ffcca42587548be5417494593198fc16ef4537fcb3507e56ecb0940f483d | e19d215278fe89455f513eea1f431a9cbd352fd26641180be69d9777a377b4b5 | c1ccncc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1-[C;D1;H3:7].C-C-C-[CH2]-[Sn](-[CH2;D2;+0:8]-[#8:9]-[Si;H0;D4;+0:10](-[CH3;D1;+0:11])(-[CH3;D1;+0:12])-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16])(-[CH2]-C-C-C)-[CH2]-C-C-C>>[C;D1;H3:7]-[c:6]1:[c:5]:[c:4]:[#7;a:3]:[c:2]:[c;H0;D3;+0:1]:1-[C;H0;D4;+0:8](-[CH3;D1... | 57 | [{"value": 57.0, "product": "C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C(=C1)C)C(O[SiH2]C(C)(C)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | A solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-bromo-4-methylpyridin (15.0 g, 38.70 mmol), tert-butyl-dimethyl-tributylstannanylmethoxy-silane (25.4 g, 58.3 mmol), and bis(triphenylphosphine)palladium(II) dichloride (0.90 g, 1.42 mmol) in 1,2dichloroethane (50 mL) was stirred at 90° C. for two days. The mixture ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.TMS ether protective group.Tin | null | c1ccncc1 | c1ccncc1 | c1ccncc1 | HBr.Sn | Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl | 0 | 0.5 | CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[CH2]O[Si](C)(C)C(C)(C)C.Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1Br>Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl>Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1C(C)(C)O[SiH2]C(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5665354fd2f7409e9a81995370c974a7 | Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1C(C)(C)O[SiH2]C(C)(C)C>>Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1CO | [F-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C(=C1)C)C(O[SiH2]C(C)(C)C)(C)C>>C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C(=C1)C)CO | CC(C)(C)[SiH2][O:24][C:23](C)(C)[c:22]1[c:2]([CH3:1])[cH:3][c:4]([N:5]([C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][cH:21]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]([C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3... | Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1C(C)(C)O[SiH2]C(C)(C)C | Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1CO | null | null | C1CCOC1 | Deprotection | OtherReaction | d7487e9652d81f9226fa8fb90bf02725deb1441d4abc97ee4fdbe439e00122e0 | ff9889ffd40f59bd281424811967f384d29acb01a2d54e10590c5a677f81d17a | c1ccncc1 | C-C(-C)(-C)-[SiH2]-[O;H0;D2;+0:1]-[C;H0;D4;+0:2](-C)(-C)-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 67 | [{"value": 67.0, "product": "C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C(=C1)C)CO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.8, "product": "C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C(=C1)C)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Tetrabutylammonium fluoride (13.9 g, 44.1 mmol) was added to a solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-methylpyridin (10.0 g, 24.3 mmol) in THF (100 mL). The reaction mixture was stirred for 3 h at room temperature. Concentration under reduced pressure followed by fl... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | null | null | c1ccncc1 | Other | C1CCOC1 | null | 3 | Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1C(C)(C)O[SiH2]C(C)(C)C>C1CCOC1>Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1CO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eb5aa5ebdc914155b2566bb3679d71a8 | BrC(Br)(Br)Br.Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1CO>>Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1CBr | C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(Br)(Br)(Br)Br.C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C(=C1)C)CO>>BrCC=1C(=CC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C | BrC(Br)(Br)[Br:24].O[CH2:23][c:22]1[c:2]([CH3:1])[cH:3][c:4]([N:5]([C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][cH:21]1>>[CH3:1][c:2]1[cH:3][c:4]([N:5]([C:6](=[O:7])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18]... | BrC(Br)(Br)Br.Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1CO | Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1CBr | null | null | ClCCl | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | c1ccncc1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 90.1 | [{"value": 90.0, "product": "BrCC=1C(=CC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.1, "product": "BrCC=1C(=CC(=NC1)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Triphenylphosphine (4.69 g, 17.9 mmol) and CBr4 (4.89 g, 14.8 mmol) was added to a solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-4-methylpyridin (5.00 g, 22.0 mmol) in dichloromethane (130 mL) at 0° C. The reaction mixture was stirred for 3 h and was then diluted with dichloromethane. The organic ph... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | c1ccncc1 | HBr | ClCCl | null | 3 | BrC(Br)(Br)Br.Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1CO>ClCCl>Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1CBr |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-67ff9859d3e345c2ae19712d6f3b494f | CCOC(=O)CC(=O)OCC.Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1CBr>>CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)OCC | C(C)(=O)OCC.C(CC(=O)OCC)(=O)OCC.[H-].[Na+].C(C)(C)(C)OC(=O)N(C(=O)OC(C)(C)C)C1=NC=C(C(=C1)C)CBr>>C(C)OC(C(C(=O)OCC)CC=1C=NC(=CC1C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:30](=[O:31])[O:32][CH2:33][CH3:34].Br[CH2:7][c:8]1[cH:9][n:10][c:11]([N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[cH:27][c:28]1[CH3:29]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10][c... | CCOC(=O)CC(=O)OCC.Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1CBr | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)OCC | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 8175b6573d6439ec7ccc45bf6b48843ab56b46dccfc6504384c4766d09f35cc7 | d1817e44576d3a158547867a56245217a593d4f828a6d6dfaa8ed11276894e44 | c1ccncc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15] | 48 | [{"value": 48.0, "product": "C(C)OC(C(C(=O)OCC)CC=1C=NC(=CC1C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.9, "product": "C(C)OC(C(C(=O)OCC)CC=1C=NC(=CC1C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a suspension of NaH (0.24 g, 6.0 mmol, 60%) in DMF (5 mL) was added diethyl malonate (0.91 mL, 6.0 mmol) and the mixture was stirred for 15 min. A solution 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-bromomethyl-4-methyl-pyridin (2.0 g, 5.0 mmol) in DMF (5 mL) was added and the resulting solution stirred for 120 min at ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ester | Ester.Ester | null | null | c1ccncc1 | HBr | CN(C)C=O | null | 0.25 | CCOC(=O)CC(=O)OCC.Cc1cc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)ncc1CBr>CN(C)C=O>CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b84a505c29024323a7f7daa2e2f9b332 | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)OCC>>CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)O | [OH-].[K+].C(C)OC(C(C(=O)OCC)CC=1C=NC(=CC1C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O>>C(C)OC(C(C(=O)O)CC=1C=NC(=CC1C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O | CC[O:32][C:30]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][c:8]1[cH:9][n:10][c:11]([N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[cH:27][c:28]1[CH3:29])=[O:31]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][c:8]1[cH:9][n:10][c:11]([N:12]([C:1... | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)OCC | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)O | null | null | C(Cl)Cl.C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 97 | [{"value": 97.0, "product": "C(C)OC(C(C(=O)O)CC=1C=NC(=CC1C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.5, "product": "C(C)OC(C(C(=O)O)CC=1C=NC(=CC1C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of KOH (141 mg, 2.52 mmol) in ethanol (2 mL) was added to a solution 2-(6-[N,N-bis(tert-butoxycarbonyl)amino]4-methyl-pyridin-3-ylmethyl)-malonic acid diethyl ester (1.1 g, 2.29 mmol) in ethanol (10 mL) and methylene chloride (4 mL) at 0° C. The mixture was stirred for 18 h at room temperature. The mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | Other | C(Cl)Cl.C(C)O | null | 18 | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)OCC>C(Cl)Cl.C(C)O>CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-bfa4f575661a4f058260736ab655e8f3 | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)O>>C=C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)OCC | C(C)NCC.C(C)OC(C(C(=O)O)CC=1C=NC(=CC1C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O.C=O.C(C)(=O)OCC>>C(C)OC(C(=C)CC=1C=NC(=CC1C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O | O=[C:1](O)[CH:2]([CH2:3][c:4]1[cH:5][n:6][c:7]([N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[cH:23][c:24]1[CH3:25])[C:26](=[O:27])[O:28][CH2:29][CH3:30]>>[CH2:1]=[C:2]([CH2:3][c:4]1[cH:5][n:6][c:7]([N:8]([C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14... | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)O | C=C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)OCC | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 485594ce7bba157615ffbb01ccede84a4e638576571b5d04649a06f3d4b7bce0 | 55e5b5078322f9f4fb0a7e9b5fc8a8cb9084e9135b447b8c441ad0800765792e | c1ccncc1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3]-[c:4]:[c:5]:[#7;a:6])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10]>>[#7;a:6]:[c:5]:[c:4]-[C:3]-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:7](=[O;D1;H0:8])-[#8:9]-[C:10] | 88 | [{"value": 88.0, "product": "C(C)OC(C(=C)CC=1C=NC(=CC1C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.6, "product": "C(C)OC(C(=C)CC=1C=NC(=CC1C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Diethylamine (0.26 g, 2.67 mmol) was added a mixture of 2-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-ylmethyl)-malonic acid monoethyl ester (1.0 g, 2.2 mmol) and 37% aq. solution of formaldehyde (0.24 g, 3.00 mmol) in methylene chloride (2 mL) at 0° C. The mixture was stirred for 16 h at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ester.Vinyl | null | null | c1ccncc1 | Other | C(Cl)Cl | null | 16 | CCOC(=O)C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)O>C(Cl)Cl>C=C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-85be6c3d5cf947ad8578ebfa34a63d26 | C=C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)OCC.CC(O)=S.CCN(CC)CC.CCOC(C)=O>>CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1.CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C | C(C)N(CC)CC.C(C)OC(C(=C)CC=1C=NC(=CC1C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)=O.C(C)(=S)O.C(C)(=O)OCC>>C(C)OC(C(CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)CSC(C)=O)=O.C(C)OC(C(CC=1C=NC(=CC1C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)CSC(C)=O)=O | [CH3:18][C:21]([O:20][C:59](=[O:19])[N:51]([C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[c:50]1[n:49][cH:48][c:47]([CH2:46][C:40]([C:38]([O:37][CH2:36][CH3:35])=[O:39])=[CH2:41])[c:67]([CH3:68])[cH:66]1)([CH3:58])[CH3:65].[S:8]=[C:9]([CH3:10])[OH:11].[CH3:7][CH2:12][N:15]([CH2:14][CH3:13])[CH2:16][CH3:32].[C... | C=C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)OCC.CC(O)=S.CCN(CC)CC.CCOC(C)=O | CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1.CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 032ef00a7acaabf6ca8902421766a9be71716253a44363dc16930c2ebd884199 | 02573f00161c0a40ac11ef724be710e73cabd6145119dfbb27fe4f0b665bb2a6 | c1ccncc1.c1ccncc1 | [C;D1;H3:1]-[C;H0;D3;+0:2](-[OH;D1;+0:3])=[S;H0;D1;+0:4].[CH3;D1;+0:5]-[CH2;D2;+0:6]-[N;H0;D3;+0:7](-[CH2;D2;+0:8]-[CH3;D1;+0:9])-[CH2;D2;+0:10]-[CH3;D1;+0:11].[C:12]-[#8:13]-[C:14](-[CH3;D1;+0:15])=[O;D1;H0:16].[C:17]-[#8:18]-[C:19](=[O;D1;H0:20])-[C;H0;D3;+0:21](=[CH2;D1;+0:22])-[C:23]-[c:24]:[c:25]:[#7;a:26]:[c:27](... | 21 | [{"value": 21.0, "product": "C(C)OC(C(CC=1C=NC(=C(C1)C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Triethylamine (0.279 mL, 2.0 mmol) was added to a solution of 2-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-ylmethyl)-acrylic acid ethyl ester (0.8 g, 1.9 mmol) in thioacetic acid (3 mL) at 0° C. The mixture was stirred at room temperature for 16 h. Ethyl acetate was added and the organic phase was washed... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ester.Ester.Ether.Ether.Substituted dicarboximide.Tertiary amine.Thiocarbonyl.Vinyl.Boc.Boc | Carbamic ester.Carbamic ester.Carbamic ester.Carbamic ester.Ester.Ester.Ether.Ether.Ether.Ether.Substituted dicarboximide.Substituted dicarboximide.Carbo-thioester.Carbo-thioester.Boc.Boc.Boc.Boc | null | c1ccncc1 | c1ccncc1.c1ccncc1 | Other | null | null | 16 | C=C(Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C)C(=O)OCC.CC(O)=S.CCN(CC)CC.CCOC(C)=O>>CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)c(C)c1.CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d41aba1fce454adcb3f51d2dde176afd | CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C>>Cc1cc(N)ncc1CC(CS)C(=O)O | C(C)OC(C(CC=1C=NC(=CC1C)N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)CSC(C)=O)=O>>NC1=CC(=C(C=N1)CC(C(=O)O)CS)C | CC[O:15][C:13]([CH:10]([CH2:9][c:8]1[c:2]([CH3:1])[cH:3][c:4]([N:5](C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)[n:6][cH:7]1)[CH2:11][S:12]C(C)=O)=[O:14]>>[CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:6][cH:7][c:8]1[CH2:9][CH:10]([CH2:11][SH:12])[C:13](=[O:14])[OH:15] | CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C | Cc1cc(N)ncc1CC(CS)C(=O)O | null | null | Cl | Reduction | OtherReaction | ff200d63748925ecb928aee95d999f108474ef3634c58d22fe1e9be9ac805fa3 | 430680ed2de5eb87de586bf5706158a5dd503c4be3ff91566980452c5549779b | c1ccncc1 | 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].C-C-[O;H0;D2;+0:6]-[C:7](=[O;D1;H0:8])-[C:9]-[C:10]-[S;H0;D2;+0:11]-C(-C)=O>>[NH2;D1;+0:1]-[c:2](:[c:3]):[#7;a:4]:[c:5].[O;D1;H0:8]=[C:7](-[OH;D1;+0:6])-[C:9]-[C:10]-[SH;D1;+0:11] | 114.8 | [{"value": 98.0, "product": "NC1=CC(=C(C=N1)CC(C(=O)O)CS)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 114.8, "product": "NC1=CC(=C(C=N1)CC(C(=O)O)CS)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 2-Acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-4-methyl-pyridin-3-yl)-propionic acid ethyl ester (36 mg, 0.072 mmol) was dissolved in conc. HCl (3.0 mL). The solution was heated to reflux for 1 h. Concentration under reduced pressure gave the title compound (18.7 mg, 98%) as the hydrochloride salt.
Con... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carbamic ester.Ester.Ether.Ether.Substituted dicarboximide.Carbo-thioester.Boc.Boc | Carboxylic acid.Primary amine.Aliphatic thiol | null | null | c1ccncc1 | HO- | Cl | null | null | CCOC(=O)C(CSC(C)=O)Cc1cnc(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1C>Cl>Cc1cc(N)ncc1CC(CS)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1d62ca02886d475b84f45385af6939a4 | CC(C)(C)OC(=O)N1CCC(CO)CC1>>CC(C)(C)OC(=O)N1CCC(C=O)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)CO.C(C)OCC>>C(C)(C)(C)OC(=O)N1CCC(CC1)C=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][OH:13])[CH2:14][CH2:15]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH:12]=[O:13])[CH2:14][CH2:15]1 | CC(C)(C)OC(=O)N1CCC(CO)CC1 | CC(C)(C)OC(=O)N1CCC(C=O)CC1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | C1CCNCC1 | [C:1]-[C:2](-[CH2;D2;+0:3]-[OH;D1;+0:4])-[C:5]>>[C:1]-[C:2](-[CH;D2;+0:3]=[O;H0;D1;+0:4])-[C:5] | 81.7 | [{"value": 81.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.7, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | Periodinane (26.9 g, 63.5 mmol) was added to a solution of 1-tert-butoxycarbonyl-piperidine-4-methanol (10.5 g, 48.8 mmol) in methylene chloride (200 mL) and the mixture was stirred for 90 min. Diethyl ether was added and precipitates were removed by extraction with 10% Na2S2O3/saturated NaHCO3 (1:1, 300 mL). The organ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | C1CC[NH]CC1 | null | C(Cl)Cl | null | 1.5 | CC(C)(C)OC(=O)N1CCC(CO)CC1>C(Cl)Cl>CC(C)(C)OC(=O)N1CCC(C=O)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a05c56976b414edf8d5d8980bc7e38dc | CC(C)(C)OC(=O)N1CCC(C=O)CC1.CCOC(=O)CC(=O)OCC>>CCOC(=O)C(=CC1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCC | C(CC(=O)OCC)(=O)OCC.C(C)(C)(C)OC(=O)N1CCC(CC1)C=O.N1CCCCC1.C(C)(=O)O>>C(C)OC(C(C(=O)OCC)=CC1CCN(CC1)C(=O)OC(C)(C)C)=O | O=[CH:7][CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:21](=[O:22])[O:23][CH2:24][CH3:25]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][CH:8]1[CH2:9][CH2:10][N:11]([C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[... | CC(C)(C)OC(=O)N1CCC(C=O)CC1.CCOC(=O)CC(=O)OCC | CCOC(=O)C(=CC1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCC | null | null | C(Cl)Cl.CCOC(=O)C | C-C Coupling | Aldol condensation | 4308c3bc8a698ffc0b4a25652616c227140ef668f7c572096e661e9937e780ad | fae8d7810715ce1cb0ea563a010deed21a5c5db9b9f45a5f7ae1c022defa3e22 | C1CCNCC1 | O=[CH;D2;+0:1]-[C:2](-[C:3])-[C:4].[C:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[CH2;D2;+0:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]>>[C:3]-[C:2](-[CH;D2;+0:1]=[C;H0;D3;+0:9](-[C:7](=[O;D1;H0:8])-[#8:6]-[C:5])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13])-[C:4] | 41.3 | [{"value": 40.0, "product": "C(C)OC(C(C(=O)OCC)=CC1CCN(CC1)C(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.3, "product": "C(C)OC(C(C(=O)OCC)=CC1CCN(CC1)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | To a solution of diethyl malonate (710 μL, 4.7 mmol) and 4-formyl-piperidine-1-carboxylic acid tert-butyl ester (1.0 g,4.7 mmol) in methylene chloride (5 mL) was added piperidine (46 μL, 0.47 mmol) and acetic acid (27 μL, 0.47 mmol). The reaction mixture was stirred for 72 h at room temperature and then for 16 h at 45°... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Ester | Ester.Ester | null | null | C1CC[NH]CC1 | HO- | C(Cl)Cl.CCOC(=O)C | null | 72 | CC(C)(C)OC(=O)N1CCC(C=O)CC1.CCOC(=O)CC(=O)OCC>C(Cl)Cl.CCOC(=O)C>CCOC(=O)C(=CC1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1dc4c076a3904857b216076645d79004 | CCOC(=O)C(=CC1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCC>>CCOC(=O)C(C(=O)OCC)C(C)C1CCN(C(=O)OC(C)(C)C)CC1 | [Li]C.C(C)OC(C(C(=O)OCC)=CC1CCN(CC1)C(=O)OC(C)(C)C)=O.[NH4+].[OH-]>>C(C)OC(C(C(=O)OCC)C(C)C1CCN(CC1)C(=O)OC(C)(C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])=[CH:12][CH:14]1[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[CH:12]([CH3:13])[CH:14]1[CH2:15][CH2:16][N:17]([C:18](=[O:... | CCOC(=O)C(=CC1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCC | CCOC(=O)C(C(=O)OCC)C(C)C1CCN(C(=O)OC(C)(C)C)CC1 | null | [Cu]I | C1CCOC1 | Miscellaneous | OtherReaction | 6586cb8fb9074fe79a2f08ccdc9c7ab8f943f0a45ff8db5202191123ff3bfd5e | 81b73c69b19b4e45eeae7092f9c28fa5c915fb74eee9edf622d890bb40e4be14 | C1CCNCC1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](=[CH;D2;+0:6]-[C:7](-[C:8])-[C:9])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5](-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13])-[CH;D3;+0:6](-[C;D1;H3:14])-[C:7](-[C:8])-[C:9] | 54.1 | [{"value": 54.0, "product": "C(C)OC(C(C(=O)OCC)C(C)C1CCN(CC1)C(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.1, "product": "C(C)OC(C(C(=O)OCC)C(C)C1CCN(CC1)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | MeLi (5.34 mL, 8.54 mmol, 1.6 M in diethyl ether) was added dropwise to a slurry of CuI (0.74 g, 3.88 mmol) in THF (5 mL) at −78° C. under argon and the mixture was stirred for 30 min. A solution of 2-(1-tert-butoxycarbonyl-piperidin4-ylmethylene)-malonic acid diethyl ester (0.69 g, 1.94 mmol) in THF (5 mL) was added d... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ester.Ester | null | null | C1CC[NH]CC1 | Other | [Cu]I.C1CCOC1 | null | 0.5 | CCOC(=O)C(=CC1CCN(C(=O)OC(C)(C)C)CC1)C(=O)OCC>[Cu]I.C1CCOC1>CCOC(=O)C(C(=O)OCC)C(C)C1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c37643589f614cb7846bdd883ea6da7d | CCOC(=O)C(C(=O)OCC)C(C)C1CCN(C(=O)OC(C)(C)C)CC1>>CCOC(=O)C(C(=O)O)C(C)C1CCN(C(=O)OC(C)(C)C)CC1 | [OH-].[K+].C(C)OC(C(C(=O)OCC)C(C)C1CCN(CC1)C(=O)OC(C)(C)C)=O.CCOC(=O)C>>C(C)OC(C(C(=O)O)C(C)C1CCN(CC1)C(=O)OC(C)(C)C)=O | CC[O:9][C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:10]([CH3:11])[CH:12]1[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]1)=[O:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[OH:9])[CH:10]([CH3:11])[CH:12]1[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([C... | CCOC(=O)C(C(=O)OCC)C(C)C1CCN(C(=O)OC(C)(C)C)CC1 | CCOC(=O)C(C(=O)O)C(C)C1CCN(C(=O)OC(C)(C)C)CC1 | null | null | C(Cl)Cl.CCO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | C1CCNCC1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 119.9 | [{"value": 119.9, "product": "C(C)OC(C(C(=O)O)C(C)C1CCN(CC1)C(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of KOH (84 mg, 1.16 mmol) in EtOH (2 mL) was added dropwise to a solution of 2-[1-(1-tert-butoxycarbonyl-piperidin-4-yl)-ethyl]-malonic acid diethyl ester (0.39 g, 1.01 mmol) in methylene chloride (4 mL) and EtOH (10 mL) at 0° C. The resulting mixture was stirred at room temperature over night. EtOAc was add... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]CC1 | Other | C(Cl)Cl.CCO | null | null | CCOC(=O)C(C(=O)OCC)C(C)C1CCN(C(=O)OC(C)(C)C)CC1>C(Cl)Cl.CCO>CCOC(=O)C(C(=O)O)C(C)C1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-38d871a641174a1f87aebfb6a9fb8167 | CCOC(=O)C(C(=O)O)C(C)C1CCN(C(=O)OC(C)(C)C)CC1>>C=C(C(=O)OCC)C(C)C1CCN(C(=O)OC(C)(C)C)CC1 | CCOC(=O)C.C=O.C(C)OC(C(C(=O)O)C(C)C1CCN(CC1)C(=O)OC(C)(C)C)=O.C(C)NCC>>C(C)(C)(C)OC(=O)N1CCC(CC1)C(C(=C)C(=O)OCC)C | O=[C:1](O)[CH:2]([C:3](=[O:4])[O:5][CH2:6][CH3:7])[CH:8]([CH3:9])[CH:10]1[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]1>>[CH2:1]=[C:2]([C:3](=[O:4])[O:5][CH2:6][CH3:7])[CH:8]([CH3:9])[CH:10]1[CH2:11][CH2:12][N:13]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])... | CCOC(=O)C(C(=O)O)C(C)C1CCN(C(=O)OC(C)(C)C)CC1 | C=C(C(=O)OCC)C(C)C1CCN(C(=O)OC(C)(C)C)CC1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 485594ce7bba157615ffbb01ccede84a4e638576571b5d04649a06f3d4b7bce0 | 55e5b5078322f9f4fb0a7e9b5fc8a8cb9084e9135b447b8c441ad0800765792e | C1CCNCC1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C:7](-[C:8])-[C;D1;H3:9]>>[C:8]-[C:7](-[C;D1;H3:9])-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6] | 49 | [{"value": 49.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)C(C(=C)C(=O)OCC)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 47.7, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)C(C(=C)C(=O)OCC)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Formaldehyde (132 mg, 1.65 mmol, 37% in water) was added to a solution of of crude 2-[1-(1-tert-butoxycarbonyl-piperidin4-yl)-ethyl]-malonic acid monoethyl ester (416 mg) in methylene chloride (2 mL) at 0° C. Diethylamine (153 μL, 1.47 mmol) was added dropwise and the mixture was stirred at room temperature over night.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ester.Vinyl | null | null | C1CC[NH]CC1 | Other | C(Cl)Cl | null | null | CCOC(=O)C(C(=O)O)C(C)C1CCN(C(=O)OC(C)(C)C)CC1>C(Cl)Cl>C=C(C(=O)OCC)C(C)C1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b53a6ec53d094e5881ace0eea6d99552 | C=C(C(=O)OCC)C(C)C1CCN(C(=O)OC(C)(C)C)CC1.CC(O)=S>>CCOC(=O)C(CSC(C)=O)C(C)C1CCN(C(=O)OC(C)(C)C)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)C(C(=C)C(=O)OCC)C.C(C)(=S)O.C(C)(=S)O.CCOC(=O)C>>C(C)(C)(C)OC(=O)N1CCC(CC1)C(C(CSC(C)=O)C(=O)OCC)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH2:7])[CH:12]([CH3:13])[CH:14]1[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]1.[S:8]=[C:9]([CH3:10])[OH:11]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH:12]([CH3:13])[CH:14]1[CH2:15][CH2:16][N:17]... | C=C(C(=O)OCC)C(C)C1CCN(C(=O)OC(C)(C)C)CC1.CC(O)=S | CCOC(=O)C(CSC(C)=O)C(C)C1CCN(C(=O)OC(C)(C)C)CC1 | null | null | null | Protection | OtherReaction | 56aa090d67fbecbea8a1963579cc34949775a09653b2b2f2795c609c60e70c77 | 5a9b0d631147b21b844b3c73866d1d81ab543538a176ebae28118ae7e39e572f | C1CCNCC1 | [C;D1;H3:1]-[C;H0;D3;+0:2](-[OH;D1;+0:3])=[S;H0;D1;+0:4].[C:5]-[C:6](-[C;D1;H3:7])-[C;H0;D3;+0:8](=[CH2;D1;+0:9])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13]>>[C:5]-[C:6](-[C;D1;H3:7])-[CH;D3;+0:8](-[CH2;D2;+0:9]-[S;H0;D2;+0:4]-[C;H0;D3;+0:2](-[C;D1;H3:1])=[O;H0;D1;+0:3])-[C:10](=[O;D1;H0:11])-[#8:12]-[C:13] | null | [] | 45 | CELSIUS | null | null | TEA (86 μL, 0.617 mmol) was added to a solution of 4-(2ethoxycarbonyl-1-methyl-allyl)-piperidine-1-carboxylic acid tert-butyl ester (0.18 g, 0.59 mmol) in thioacetic acid (2 mL) at 0° C. After stirring for 6 h more thioacetic acid (2 mL) was added and the mixture was stirred at 45° C. over night. EtOAc was added and th... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Thiocarbonyl.Vinyl | Ester.Carbo-thioester | null | null | C1CC[NH]CC1 | null | null | 45 | null | C=C(C(=O)OCC)C(C)C1CCN(C(=O)OC(C)(C)C)CC1.CC(O)=S>>CCOC(=O)C(CSC(C)=O)C(C)C1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-9261c70df4e7495e965dc2f338370af3 | CCOC(=O)C(CSC(C)=O)C(C)C1CCN(C(=O)OC(C)(C)C)CC1>>CCOC(=O)C(CSC(C)=O)C(C)C1CCNCC1 | C(=O)(C(F)(F)F)O.C(C)(C)(C)OC(=O)N1CCC(CC1)C(C(CSC(C)=O)C(=O)OCC)C>>C(C)OC(C(C(C)C1CCNCC1)CSC(C)=O)=O | CC(C)(C)OC(=O)[N:17]1[CH2:16][CH2:15][CH:14]([CH:12]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH3:13])[CH2:19][CH2:18]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7][S:8][C:9]([CH3:10])=[O:11])[CH:12]([CH3:13])[CH:14]1[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]1 | CCOC(=O)C(CSC(C)=O)C(C)C1CCN(C(=O)OC(C)(C)C)CC1 | CCOC(=O)C(CSC(C)=O)C(C)C1CCNCC1 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | C1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 80 | [{"value": 54.0, "product": "C(C)OC(C(C(C)C1CCNCC1)CSC(C)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.0, "product": "C(C)OC(C(C(C)C1CCNCC1)CSC(C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 90 | MINUTE | TFA (2 mL) was added to a solution of 4-(3-acetylsulfanyl-2-ethoxycarbonyl-1-methyl-propyl)-piperidine-1-carboxylic acid tert-butyl ester (0.17 g, 0.439 mmol) in methylene chloride (10 mL). The reaction was stirred for 90 min and concentrated under reduced pressure. The crude product was purified using HPLC (10→50% ace... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1 | HO- | C(Cl)Cl | null | 1.5 | CCOC(=O)C(CSC(C)=O)C(C)C1CCN(C(=O)OC(C)(C)C)CC1>C(Cl)Cl>CCOC(=O)C(CSC(C)=O)C(C)C1CCNCC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4c6df6aa7f004641b5850608bb4b3299 | CCOC(=O)C(CSC(C)=O)C(C)C1CCNCC1>>CC(C1CCNCC1)C(CS)C(=O)O | Cl.OC(=O)C(F)(F)F.C(C)OC(C(C(C)C1CCNCC1)CSC(C)=O)=O>>SCC(C(=O)O)C(C)C1CCNCC1 | CC[O:14][C:12]([CH:9]([CH:2]([CH3:1])[CH:3]1[CH2:4][CH2:5][NH:6][CH2:7][CH2:8]1)[CH2:10][S:11]C(C)=O)=[O:13]>>[CH3:1][CH:2]([CH:3]1[CH2:4][CH2:5][NH:6][CH2:7][CH2:8]1)[CH:9]([CH2:10][SH:11])[C:12](=[O:13])[OH:14] | CCOC(=O)C(CSC(C)=O)C(C)C1CCNCC1 | CC(C1CCNCC1)C(CS)C(=O)O | null | null | null | Reduction | OtherReaction | 1bcd8cbb2f136b4bcba1690e9ba45c4e43c89ba76f0e22de82a7d3fe318c82a9 | 5654c46fe4cb226f88ec3c899c7f9be1825c357673ea686958f9ef4883ee1db3 | C1CCNCC1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[S;H0;D2;+0:6]-C(-C)=O>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[C:4]-[C:5]-[SH;D1;+0:6] | 134.6 | [{"value": 134.6, "product": "SCC(C(=O)O)C(C)C1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Conc. hydrochloric acid (4 mL) was added to 2-acetylsulfanylmethyl-3-piperidin4-yl-butyric acid ethyl ester TFA salt (0.101 g, 0.252 mmol) under argon. The reaction was heated to reflux for 5 h and then concentrated under reduced pressure to give a diastereomeric mixture of the title compound (73.7 mg) as the hydrochlo... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Carbo-thioester | Carboxylic acid.Aliphatic thiol | null | null | C1CCNCC1 | HO- | null | null | null | CCOC(=O)C(CSC(C)=O)C(C)C1CCNCC1>>CC(C1CCNCC1)C(CS)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ef027323b7f14718817f3146fc9387e1 | CC(C)(C)OC(=O)Nc1ccc(CO)cn1>>CC(C)(C)OC(=O)Nc1ccc(C=O)cn1 | C(C)(C)(C)OC(NC1=NC=C(C=C1)CO)=O>>C(C)(C)(C)OC(NC1=NC=C(C=C1)C=O)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([CH2:13][OH:14])[cH:15][n:16]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][cH:11][c:12]([CH:13]=[O:14])[cH:15][n:16]1 | CC(C)(C)OC(=O)Nc1ccc(CO)cn1 | CC(C)(C)OC(=O)Nc1ccc(C=O)cn1 | null | null | CS(=O)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccncc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 78 | [{"value": 78.0, "product": "C(C)(C)(C)OC(NC1=NC=C(C=C1)C=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.9, "product": "C(C)(C)(C)OC(NC1=NC=C(C=C1)C=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | 5 (5-hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (7.00 g, 31.2 mmol) was dissolved in dry DMSO (50 mL) and the reaction flask immersed in a waterbath at 15° C. TEA (13.1 ml, 94.0 mmol) was added, followed by sulfur trioxide pyridine complex (15.0 g, 94.0 mmol) in portions. The reaction mixture was stirre... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccncc1 | null | CS(=O)C | null | 0.75 | CC(C)(C)OC(=O)Nc1ccc(CO)cn1>CS(=O)C>CC(C)(C)OC(=O)Nc1ccc(C=O)cn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-855ca57819ec4d568df1a98193a2fafc | CC(C)(C)OC(=O)Nc1ccc(C=O)cn1.CCOC(=O)CC(=O)OCC>>CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC | C(CC(=O)OCC)(=O)OCC.C(C)(C)(C)OC(NC1=NC=C(C=C1)C=O)=O.N1CCCCC1.C(C)(=O)O>>C(C)OC(C(C(=O)OCC)=CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | O=[CH:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[n:20][cH:21]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:22](=[O:23])[O:24][CH2:25][CH3:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[CH:7][c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:... | CC(C)(C)OC(=O)Nc1ccc(C=O)cn1.CCOC(=O)CC(=O)OCC | CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC | null | null | CCCCCCC.C(Cl)Cl.CN(C)C=O | C-C Coupling | Aldol condensation | 4308c3bc8a698ffc0b4a25652616c227140ef668f7c572096e661e9937e780ad | fae8d7810715ce1cb0ea563a010deed21a5c5db9b9f45a5f7ae1c022defa3e22 | c1ccncc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6].[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:7]-[#8:8]-[C:9](=[O;D1;H0:10])-[C;H0;D3;+0:11](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]:[#7;a:5]:[c:6])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15] | 40.3 | [{"value": 40.0, "product": "C(C)OC(C(C(=O)OCC)=CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.3, "product": "C(C)OC(C(C(=O)OCC)=CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 72 | HOUR | To a solution of diethyl malonate (710 μL, 4.7 mmol) and (5-formyl-pyridin-2-yl)-carbamic acid tert-butyl ester (1.04 g, 4.7 mmol) in methylene chloride/DMF (1:1, 5 mL) was added piperidine (46 μL, 0.47 mmol) and acetic acid (27 μL, 0.47 mmol). The reaction mixture was stirred for 72 h at room temperature and then for ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Ester | Ester.Ester | null | null | c1ccncc1 | HO- | CCCCCCC.C(Cl)Cl.CN(C)C=O | null | 72 | CC(C)(C)OC(=O)Nc1ccc(C=O)cn1.CCOC(=O)CC(=O)OCC>CCCCCCC.C(Cl)Cl.CN(C)C=O>CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b2e368cb3ea14d72b8d97f1aee77e1cd | CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC>>CCOC(=O)C(C(=O)OCC)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1 | [Li]C.C(C)OC(C(C(=O)OCC)=CC=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.[NH4+].[OH-]>>C(C)OC(C(C(=O)OCC)C(C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])=[CH:12][c:14]1[cH:15][cH:16][c:17]([NH:18][C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[n:26][cH:27]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[O:9][CH2:10][CH3:11])[CH:12]([CH3:13])[c:14]1[cH:15][cH:16][c:17]([NH:18][C:19]... | CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC | CCOC(=O)C(C(=O)OCC)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1 | null | [Cu]I | C1CCOC1 | Miscellaneous | OtherReaction | 6586cb8fb9074fe79a2f08ccdc9c7ab8f943f0a45ff8db5202191123ff3bfd5e | 81b73c69b19b4e45eeae7092f9c28fa5c915fb74eee9edf622d890bb40e4be14 | c1ccncc1 | [C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15]>>[C:1]-[#8:2]-[C:3](=[O;D1;H0:4])-[CH;D3;+0:5](-[C:12](=[O;D1;H0:13])-[#8:14]-[C:15])-[CH;D3;+0:6](-[C;D1;H3:16])-[c:7](:[c:8]):[c:9]:[#7;a:10]:[c:11] | 82.6 | [{"value": 82.4, "product": "C(C)OC(C(C(=O)OCC)C(C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.6, "product": "C(C)OC(C(C(=O)OCC)C(C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | MeLi (6.5 mL, 10.4 mmol, 1.6 M in diethyl ether) was added dropwise to a slurry of CuI (0.9 g, 4.73 mmol) in THF (28 mL) at −78° C. under argon. The reaction mixture was stirred for 30 min. A solution of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethylene)-malonic acid diethyl ester (0.84 g, 2.3 mmol) in THF (7 mL) was... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Ester.Ester | null | null | c1ccncc1 | Other | [Cu]I.C1CCOC1 | null | 0.5 | CCOC(=O)C(=Cc1ccc(NC(=O)OC(C)(C)C)nc1)C(=O)OCC>[Cu]I.C1CCOC1>CCOC(=O)C(C(=O)OCC)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cd61fcaf6d09420faf778f4a0e3fa1f3 | CCOC(=O)C(C(=O)OCC)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1>>CCOC(=O)C(C(=O)O)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1 | [OH-].[K+].C(C)OC(C(C(=O)OCC)C(C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.[OH-].[K+]>>C(C)OC(C(C(=O)O)C(C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | CC[O:9][C:7]([CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:10]([CH3:11])[c:12]1[cH:13][cH:14][c:15]([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[n:24][cH:25]1)=[O:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[OH:9])[CH:10]([CH3:11])[c:12]1[cH:13][cH:14][c:15]([NH:16][C:17](=[O:18])[O:19][C:2... | CCOC(=O)C(C(=O)OCC)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1 | CCOC(=O)C(C(=O)O)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1 | null | null | C(Cl)Cl.CCO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccncc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](-[#8:6])=[O;D1;H0:7]>>[#8:6]-[C:5](=[O;D1;H0:7])-[C:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 65.2 | [{"value": 65.0, "product": "C(C)OC(C(C(=O)O)C(C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.2, "product": "C(C)OC(C(C(=O)O)C(C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of KOH (113.6 mg, 2.04 mmol) in EtOH (2 mL) was added dropwise to a solution of 2-[1-(6-tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-malonic acid diethyl ester (0.7 g, 1.84 mmol) in methylene chloride (4 mL) and EtOH (10 mL) at 0° C. under argon and the reaction mixture was stirred over night. 1M KOH (100 m... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1 | Other | C(Cl)Cl.CCO | null | null | CCOC(=O)C(C(=O)OCC)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1>C(Cl)Cl.CCO>CCOC(=O)C(C(=O)O)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e8dccdb06f9e44fabf50426169d54b15 | CCOC(=O)C(C(=O)O)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1>>C=C(C(=O)OCC)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1 | CCOC(=O)C.C(C)NCC.C(C)OC(C(C(=O)O)C(C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O.C=O>>C(C)OC(C(=C)C(C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O | O=[C:1](O)[CH:2]([C:3](=[O:4])[O:5][CH2:6][CH3:7])[CH:8]([CH3:9])[c:10]1[cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[n:22][cH:23]1>>[CH2:1]=[C:2]([C:3](=[O:4])[O:5][CH2:6][CH3:7])[CH:8]([CH3:9])[c:10]1[cH:11][cH:12][c:13]([NH:14][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3... | CCOC(=O)C(C(=O)O)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1 | C=C(C(=O)OCC)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 485594ce7bba157615ffbb01ccede84a4e638576571b5d04649a06f3d4b7bce0 | 55e5b5078322f9f4fb0a7e9b5fc8a8cb9084e9135b447b8c441ad0800765792e | c1ccncc1 | O-[C;H0;D3;+0:1](=O)-[CH;D3;+0:2](-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6])-[C:7](-[C;D1;H3:8])-[c:9]:[c:10]:[#7;a:11]>>[#7;a:11]:[c:10]:[c:9]-[C:7](-[C;D1;H3:8])-[C;H0;D3;+0:2](=[CH2;D1;+0:1])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6] | 41.1 | [{"value": 41.0, "product": "C(C)OC(C(=C)C(C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 41.1, "product": "C(C)OC(C(=C)C(C)C=1C=NC(=CC1)NC(=O)OC(C)(C)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Diethylamine (0.153 mL, 1.473 mmol) was added to a solution of 2-[1-(6-tert-butoxycarbonylamino-pyridin-3-yl)-ethyl]-malonic acid monoethyl ester (423 mg, 1.2 mmol) and formaldehyde (132 mg, 1.626 mmol, 36% in water) in methylene chloride (2 mL) at 0° C. under argon. The mixture was stirred at room temperature over nig... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ester | Ester.Vinyl | null | null | c1ccncc1 | Other | C(Cl)Cl | null | null | CCOC(=O)C(C(=O)O)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1>C(Cl)Cl>C=C(C(=O)OCC)C(C)c1ccc(NC(=O)OC(C)(C)C)nc1 |
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