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-0387783899c642a8b7eb4ba379bcdf5d | ord-58ac291c943e4c7ab3a44a9faf264ba6 | CCN.CO[C@@H]1O[C@H](C(=O)O)[C@@H]2OC(C)(C)O[C@@H]12>>CCNC(=O)[C@H]1O[C@@H](OC)[C@@H]2OC(C)(C)O[C@@H]21 | C(C)OCC.C(C(=O)Cl)(=O)Cl.CO[C@@H]1O[C@@H]([C@H]2[C@H]1OC(O2)(C)C)C(=O)O.C(C)N>>C(C)NC(=O)[C@H]1O[C@H]([C@@H]2OC(O[C@@H]21)(C)C)OC | [CH3:1][CH2:2][NH2:3].O[C:4](=[O:5])[C@H:6]1[O:7][C@@H:8]([O:9][CH3:10])[C@@H:11]2[O:12][C:13]([CH3:14])([CH3:15])[O:16][C@@H:17]12>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@H:6]1[O:7][C@@H:8]([O:9][CH3:10])[C@@H:11]2[O:12][C:13]([CH3:14])([CH3:15])[O:16][C@H:17]12 | CCN.CO[C@@H]1O[C@H](C(=O)O)[C@@H]2OC(C)(C)O[C@@H]12 | CCNC(=O)[C@H]1O[C@@H](OC)[C@@H]2OC(C)(C)O[C@@H]21 | null | CN(C=O)C.CN(C=O)C | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | C1O[C@H]2COC[C@H]2O1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#8:4]-[C:5])-[C:6]-[#8:7].[C;D1;H3:8]-[C:9]-[NH2;D1;+0:10]>>[#8:7]-[C:6]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9]-[C;D1;H3:8])-[#8:4]-[C:5] | 94.1 | [{"value": 94.1, "product": "C(C)NC(=O)[C@H]1O[C@H]([C@@H]2OC(O[C@@H]21)(C)C)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Oxalyl chloride (14.0 ml, 160 mmol) was added dropwise to a stirred solution of (3aR,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid (J. Amer. Chem. Soc., 80, 5168–5173 (1958)) (23.30 g, 107 mmol) in anhydrous dichloromethane (120 ml) and N,N-dimethylformamide (2 drops) and the mixt... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1O[C@H]2COC[C@H]2O1 | HO- | CN(C=O)C.CN(C=O)C.ClCCl | null | 3 | CCN.CO[C@@H]1O[C@H](C(=O)O)[C@@H]2OC(C)(C)O[C@@H]12>CN(C=O)C.CN(C=O)C.ClCCl>CCNC(=O)[C@H]1O[C@@H](OC)[C@@H]2OC(C)(C)O[C@@H]21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a65621b973a4cf9ad3c7036ebba211a | CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O.COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1>>COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]3OC(C)=O)c2n1 | C/C(=N\[Si](C)(C)C)/O[Si](C)(C)C.C1(=CC=CC=C1)C(CNC1=C2N=CNC2=NC(=N1)C(=O)OC)C1=CC=CC=C1.C(C)(=O)O[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O.FC(S(=O)(=O)O[Si](C)(C)C)(F)F>>C(C)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C)=O)COC(C)=O)N1C2=NC(=NC(=C2N=C1)NCC(C1=CC=CC=C1)C1=CC=CC=C1)C(=O)OC | CC(=O)O[C@@H:27]1[O:28][C@H:29]([CH2:30][O:31][C:32]([CH3:33])=[O:34])[C@@H:35]([O:36][C:37]([CH3:38])=[O:39])[C@H:40]1[O:41][C:42]([CH3:43])=[O:44].[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6][c:7]([NH:8][CH2:9][CH:10]([c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]2[n:24][cH:25]... | CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O.COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1 | COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]3OC(C)=O)c2n1 | null | null | ClC(C)(Cl)Cl.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | a90222e67a4a22678b87b59d1ecec052c8245214c445cc6a40c830f6056425a0 | 555d70919b361b350c80f46e885ff5cda87616c212c907f1056db36bb1eb2375 | c1ccc(C(CNc2ncnc3c2ncn3[C@H]2CCCO2)c2ccccc2)cc1 | C-C(=O)-O-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-[C:4]-[C:5]-1-[#8:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9].[#8:10]-[C:11](=[O;D1;H0:12])-[c:13]1:[#7;a:14]:[c:15]2:[nH;D2;+0:16]:[c:17]:[#7;a:18]:[c:19]:2:[c:20]:[#7;a:21]:1>>[#8:10]-[C:11](=[O;D1;H0:12])-[c:13]1:[#7;a:14]:[c:15]2:[c:19](:[#7;a:18]:[c:17]:[n;H0;D3;+0:16]:2-[C@@H;D3;+0:1... | 80.7 | [{"value": 80.7, "product": "C(C)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C)=O)COC(C)=O)N1C2=NC(=NC(=C2N=C1)NCC(C1=CC=CC=C1)C1=CC=CC=C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of methyl 6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate (Preparation 7) (1.5 g, 4.02 mmol) in 1,1,1-trichloroethane (40 ml) was treated with N,O-bis(trimethylsilyl)acetamide (4.8 ml, 19.6 mmol). The mixture was heated under reflux for two hours. The solution was allowed to cool to room temperature a... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Ether | C1CCOC1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1CCOC1 | c1ccccc1.c1ccccc1.c1ncc2[nH]cnc2n1.C1CCOC1 | HO- | ClC(C)(Cl)Cl.C(C)(=O)OCC | null | null | CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O.COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1>ClC(C)(Cl)Cl.C(C)(=O)OCC>COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]3OC(C)=O)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3bfef3acea604c6e95d59fcc73d37c77 | COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]3OC(C)=O)c2n1>>COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1 | C(C)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C)=O)COC(C)=O)N1C2=NC(=NC(=C2N=C1)NCC(C1=CC=CC=C1)C1=CC=CC=C1)C(=O)OC.C([O-])([O-])=O.[Na+].[Na+]>>O[C@H]1[C@@H](O[C@@H]([C@H]1O)CO)N1C2=NC(=NC(=C2N=C1)NCC(C1=CC=CC=C1)C1=CC=CC=C1)C(=O)OC | CC(=O)[O:31][CH2:30][C@H:29]1[O:28][C@@H:27]([n:26]2[cH:25][n:24][c:23]3[c:7]([NH:8][CH2:9][CH:10]([c:11]4[cH:12][cH:13][cH:14][cH:15][cH:16]4)[c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[n:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[n:37][c:36]32)[C@H:34]([O:35]C(C)=O)[C@@H:32]1[O:33]C(C)=O>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[n:6... | COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]3OC(C)=O)c2n1 | COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1 | null | null | CO | Reduction | OtherReaction | b1205f31a625dd524c4abcf6ea407c1a38966308677d8535d59411f69b7afe49 | 53784a05a6c1858c11deb702d4a1392e7852c783da9a57d4771755f87682c932 | c1ccc(C(CNc2ncnc3c2ncn3[C@H]2CCCO2)c2ccccc2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]1-[#8:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C(-C)=O)-[C:8]-1-[O;H0;D2;+0:9]-C(-C)=O>>[OH;D1;+0:1]-[C:2]-[C:3]1-[#8:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-1-[OH;D1;+0:9] | 93.6 | [{"value": 93.6, "product": "O[C@H]1[C@@H](O[C@@H]([C@H]1O)CO)N1C2=NC(=NC(=C2N=C1)NCC(C1=CC=CC=C1)C1=CC=CC=C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of methyl 9-{(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-[(acetyloxy)methyl]-tetrahydro-2-furanyl}-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate (Preparation 15) (2.0 g, 3.17 mmol), sodium carbonate (35 mg) and dry methanol (40 ml) was stirred at room temperature for 3.5 hours. The solvent was removed under re... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Primary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1ccccc1.c1ccccc1.c1ncc2[nH]cnc2n1.C1CCOC1 | HO- | CO | null | null | COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]3OC(C)=O)c2n1>CO>COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-32838b2a0dea4bfebe8540de2786d989 | COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1.NCCN>>NCCNC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1 | O[C@H]1[C@@H](O[C@@H]([C@H]1O)CO)N1C2=NC(=NC(=C2N=C1)NCC(C1=CC=CC=C1)C1=CC=CC=C1)C(=O)OC.C(CN)N>>NCCNC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)CO)NCC(C1=CC=CC=C1)C1=CC=CC=C1 | CO[C:5](=[O:6])[c:7]1[n:8][c:9]([NH:10][CH2:11][CH:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[c:25]2[n:26][cH:27][n:28]([C@@H:29]3[O:30][C@H:31]([CH2:32][OH:33])[C@@H:34]([OH:35])[C@H:36]3[OH:37])[c:38]2[n:39]1.[NH2:1][CH2:2][CH2:3][NH2:4]>>[NH2:1][CH2:2][CH2:3][NH:4][C... | COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1.NCCN | NCCNC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1 | null | null | ClCCl | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(C(CNc2ncnc3c2ncn3[C@H]2CCCO2)c2ccccc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5](:[#7;a:6]):[c:7](:[#7;a:8]):[c:9]:[#7;a:10]:1.[C:11]-[C:12]-[NH2;D1;+0:13]>>[#7;a:8]:[c:7]1:[c:9]:[#7;a:10]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[C:12]-[C:11]):[#7;a:4]:[c:5]:1:[#7;a:6] | 78.2 | [{"value": 78.0, "product": "NCCNC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)CO)NCC(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.2, "product": "NCCNC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)CO)NCC(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCEN... | 105 | CELSIUS | null | null | A mixture of methyl 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate (Preparation 16) (0.52 g, 1.03 mmol) and 1,2-ethylenediamine (0.6 g, 10 mmol) was heated at 105° C. for 3 hours. The mixture was dissolved in a little dichloromethane and purifi... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ncc2[nH]cnc2n1.C1CCOC1 | HO- | ClCCl | 105 | null | COC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1.NCCN>ClCCl>NCCNC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7efd89374aa24ed08aa7d37e2d91e9b1 | CC(C)C1CCNCC1.O=C1c2ccccc2C(=O)N1CCBr>>CC(C)C1CCN(CCN2C(=O)c3ccccc3C2=O)CC1 | C(C)(C)C1CCNCC1.BrCCN1C(C=2C(C1=O)=CC=CC2)=O.C([O-])([O-])=O.[K+].[K+]>>C(C)(C)C1CCN(CC1)CCN1C(C2=CC=CC=C2C1=O)=O | [CH3:1][CH:2]([CH3:3])[CH:4]1[CH2:5][CH2:6][NH:7][CH2:21][CH2:22]1.Br[CH2:8][CH2:9][N:10]1[C:11](=[O:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]2[C:19]1=[O:20]>>[CH3:1][CH:2]([CH3:3])[CH:4]1[CH2:5][CH2:6][N:7]([CH2:8][CH2:9][N:10]2[C:11](=[O:12])[c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]3[C:19]2=[O:20])[CH2:21][CH2:22... | CC(C)C1CCNCC1.O=C1c2ccccc2C(=O)N1CCBr | CC(C)C1CCN(CCN2C(=O)c3ccccc3C2=O)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1c2ccccc2C(=O)N1CCN1CCCCC1 | Br-[CH2;D2;+0:1]-[C:2]-[#7:3](-[C:4]=[O;D1;H0:5])-[C:6]=[O;D1;H0:7].[C:8]-[C:9]-[NH;D2;+0:10]-[C:11]-[C:12]>>[C:8]-[C:9]-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[C:2]-[#7:3](-[C:4]=[O;D1;H0:5])-[C:6]=[O;D1;H0:7])-[C:11]-[C:12] | 54.4 | [{"value": 54.4, "product": "C(C)(C)C1CCN(CC1)CCN1C(C2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 4-isopropylpiperidine (3.3 g, 20.2 mmol), N-(2-bromoethyl)phthalimide (5.4 g, 21.3 mmol), potassium carbonate (5.9 g, 45.4 mmol) and acetonitrile (100 ml) and was heated under reflux for 2.5 hours then stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue pa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2c(c1)C[NH]C2 | HBr | C(C)#N | null | 8 | CC(C)C1CCNCC1.O=C1c2ccccc2C(=O)N1CCBr>C(C)#N>CC(C)C1CCN(CCN2C(=O)c3ccccc3C2=O)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a37b355baf0d4ccb87189a29d7e7e818 | CC(C)=O.NC1CCCC1>>CC(C)NC1CCCC1 | C1(CCCC1)N.CC(=O)C>>C(C)(C)NC1CCCC1 | O=[C:2]([CH3:1])[CH3:3].[NH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1>>[CH3:1][CH:2]([CH3:3])[NH:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1 | CC(C)=O.NC1CCCC1 | CC(C)NC1CCCC1 | null | [OH-].[OH-].[Pd+2] | null | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 4940e8ed9a0db9bde699fdcdc3aff2cff0409c19478aa0ed1acfd98213338adf | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | C1CCCC1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3].[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7]>>[C:4]-[C:5](-[NH;D2;+0:6]-[CH;D3;+0:1](-[C;D1;H3:2])-[C;D1;H3:3])-[C:7] | null | [] | null | null | null | null | Peariman's catalyst (20% w/w palladium hydroxide-on-carbon) (1.5 g) was added to a solution of cyclopentylamine (15 ml, 0.21 mol) in acetone (200 ml). The reaction mixture was stirred under an atmosphere of hydrogen gas at 414 kPa (60 psi). After stirring for 16 hours the reaction mixture was filtered through Arbocel (... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | null | null | C1CCCC1 | Other | [OH-].[OH-].[Pd+2] | null | null | CC(C)=O.NC1CCCC1>[OH-].[OH-].[Pd+2]>CC(C)NC1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2edc0f68f55d4d2e9a504b31994f60af | CC(C)NC1CCCC1.N#CCO>>CC(C)N(CC#N)C1CCCC1 | OCC#N.C(C)(C)NC1CCCC1>>C1(CCCC1)N(C(C)C)CC#N | [CH3:1][CH:2]([CH3:3])[NH:4][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1.O[CH2:5][C:6]#[N:7]>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][C:6]#[N:7])[CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1 | CC(C)NC1CCCC1.N#CCO | CC(C)N(CC#N)C1CCCC1 | null | null | O.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f33a8d71b7dbaa463dcb87d1e5073e084c21a5fbc935ce82a22b6d65293f45d1 | 87693a475e46c41583976158ec46dcaf8be8cc05c5635654a6a68033770f8d5c | C1CCCC1 | O-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[C:4]-[C:5](-[NH;D2;+0:6]-[C:7](-[C;D1;H3:8])-[C;D1;H3:9])-[C:10]>>[C:4]-[C:5](-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3])-[C:7](-[C;D1;H3:8])-[C;D1;H3:9])-[C:10] | null | [] | null | null | null | null | Hydroxyacetonitrile (8.2 ml of a 70% w/w solution in water, 0.1 mol) was added to a solution of N-isopropylcyclopentanamine (11.43 g, 0.09 mol) (Preparation 23) in ethanol (60 ml). The reaction mixture was heated under reflux for 3 hours, allowed to cool and the solvent removed under reduced pressure. The residue was p... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | null | null | C1CCCC1 | HO- | O.C(C)O | null | null | CC(C)NC1CCCC1.N#CCO>O.C(C)O>CC(C)N(CC#N)C1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6a39682c48824103b1827335e43915c2 | CC(C)N(CC#N)C1CCCC1>>CC(C)N(CCN)C1CCCC1 | [OH-].[Na+].[H-].[Al+3].[Li+].[H-].[H-].[H-].C1(CCCC1)N(C(C)C)CC#N.O>>C1(CCCC1)N(CCN)C(C)C | [CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][C:6]#[N:7])[CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][NH2:7])[CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12]1 | CC(C)N(CC#N)C1CCCC1 | CC(C)N(CCN)C1CCCC1 | null | null | O1CCCC1 | Reduction | Reduction of nitrile to amine | 65bec2d9f430701d30dc9fcbe1c5418f3dfa174d67be035c50edfc71895dc9c7 | e8d1bc928b94bd4f5bf4b23363ce8f88b1ce7d146ba93829e7b8ad8dbe0007a7 | C1CCCC1 | [#7:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4]>>[#7:1]-[C:2]-[CH2;D2;+0:3]-[NH2;D1;+0:4] | 9.2 | [{"value": 9.2, "product": "C1(CCCC1)N(CCN)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 20 | MINUTE | Lithium aluminium hydride (66 ml of a 1 molar solution in tetrahydrofuran, 0.066 mol) was added to a stirred solution of [cyclopentyl(isopropyl)amino]acetonitrile (10 g, 0.66 mol) (Preparation 24) in tetrahydrofuran (100 ml) at 0° C. The reaction mixture was stirred at 0° C. for 20 minutes and then heated under reflux ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | C1CCCC1 | null | O1CCCC1 | 0 | 0.333333 | CC(C)N(CC#N)C1CCCC1>O1CCCC1>CC(C)N(CCN)C1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2b195feacae64a78b2bbb43fd351fd03 | CC(C)NC1CCCCC1.N#CCO>>CC(C)N(CC#N)C1CCCCC1 | C(C)(C)NC1CCCCC1.OCC#N>>C1(CCCCC1)N(C(C)C)CC#N | [CH3:1][CH:2]([CH3:3])[NH:4][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1.O[CH2:5][C:6]#[N:7]>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][C:6]#[N:7])[CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1 | CC(C)NC1CCCCC1.N#CCO | CC(C)N(CC#N)C1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f33a8d71b7dbaa463dcb87d1e5073e084c21a5fbc935ce82a22b6d65293f45d1 | 87693a475e46c41583976158ec46dcaf8be8cc05c5635654a6a68033770f8d5c | C1CCCCC1 | O-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[C:4]-[C:5](-[NH;D2;+0:6]-[C:7](-[C;D1;H3:8])-[C;D1;H3:9])-[C:10]>>[C:4]-[C:5](-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3])-[C:7](-[C;D1;H3:8])-[C;D1;H3:9])-[C:10] | null | [] | null | null | null | null | Prepared from N-isopropylcyclohexylamine and hydroxyacetonitrile by a similar method to Preparation 24.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | null | null | C1CCCCC1 | HO- | null | null | null | CC(C)NC1CCCCC1.N#CCO>>CC(C)N(CC#N)C1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f2ee14fab341482e9a74a7bb84f63a09 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](O)[C@@H]1O.NCCCN>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCCN)nc32)[C@H](O)[C@@H]1O | C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)OC)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1.NCCCN>>NCCCNC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)NCC(C1=CC=CC=C1)C1=CC=CC=C1 | CO[C:31]([c:30]1[n:29][c:13]([NH:14][CH2:15][CH:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:12]2[n:11][cH:10][n:9]([C@@H:8]3[O:7][C@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[C@@H:42]([OH:43])[C@H:40]3[OH:41])[c:39]2[n:38]1)=[O:32].[NH2:33][CH2:34][CH2:35][CH2:36][NH2:37]... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](O)[C@@H]1O.NCCCN | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCCN)nc32)[C@H](O)[C@@H]1O | null | null | ClCCl | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(C(CNc2ncnc3c2ncn3[C@H]2CCCO2)c2ccccc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[#7;a:10]:1.[C:11]-[C:12]-[NH2;D1;+0:13]>>[#7;a:7]:[c:6]1:[c:5]:[#7;a:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[C:12]-[C:11]):[#7;a:10]:[c:8]:1:[#7;a:9] | 58.4 | [{"value": 58.0, "product": "NCCCNC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)NCC(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.4, "product": "NCCCNC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)NCC(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CA... | 100 | CELSIUS | null | null | A mixture of methyl 6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxylate (Preparation 9) (0.35 g, 0.64 mmol) and 1,3-diaminopropane (0.45 g, 6.1 mmol) was heated at 100° C. for 3 hours. The mixture was dissolved in a little dichloromethane and... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1 | HO- | ClCCl | 100 | null | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](O)[C@@H]1O.NCCCN>ClCCl>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCCN)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9a7c7421a5744e4b9cb52f422cdeec91 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](O)[C@@H]1O.NC1CCN(Cc2ccccc2)CC1>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NC4CCN(Cc5ccccc5)CC4)nc32)[C@H](O)[C@@H]1O | C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)OC)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1.C(C1=CC=CC=C1)N1CCC(CC1)N>>C(C1=CC=CC=C1)N1CCC(CC1)NC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)NCC(C1=CC=CC=C1)C1=CC=CC=C1 | CO[C:31]([c:30]1[n:29][c:13]([NH:14][CH2:15][CH:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:12]2[n:11][cH:10][n:9]([C@@H:8]3[O:7][C@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[C@@H:51]([OH:52])[C@H:49]3[OH:50])[c:48]2[n:47]1)=[O:32].[NH2:33][CH:34]1[CH2:35][CH2:36][N:37]([... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](O)[C@@H]1O.NC1CCN(Cc2ccccc2)CC1 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NC4CCN(Cc5ccccc5)CC4)nc32)[C@H](O)[C@@H]1O | null | null | ClCCl | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=C(NC1CCN(Cc2ccccc2)CC1)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@H]3CCCO3)c2n1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[#7;a:10]:1.[C:11]-[C:12](-[NH2;D1;+0:13])-[C:14]>>[#7;a:7]:[c:6]1:[c:5]:[#7;a:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[C:12](-[C:11])-[C:14]):[#7;a:10]:[c:8]:1:[#7;a:9] | 80 | [{"value": 80.0, "product": "C(C1=CC=CC=C1)N1CCC(CC1)NC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)NCC(C1=CC=CC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.5, "product": "C(C1=CC=CC=C1)N1CCC(CC1)NC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)NCC(... | 105 | CELSIUS | null | null | A mixture of methyl 6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxylate (Preparation 9) (1.0 g, 1.83 mmol) and 1-benzyl-4-piperidinylamine (2.4 ml, 11 mmol) was heated at 105° C. for 4 hours. The mixture was dissolved in a little dichlorometh... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1.C1CC[NH]CC1.c1ccccc1 | HO- | ClCCl | 105 | null | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](O)[C@@H]1O.NC1CCN(Cc2ccccc2)CC1>ClCCl>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NC4CCN(Cc5ccccc5)CC4)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9f53c36c189340a68a9f5c76b3e8b421 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NC4CCN(Cc5ccccc5)CC4)nc32)[C@H](O)[C@@H]1O>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NC4CCNCC4)nc32)[C@H](O)[C@@H]1O | C(C1=CC=CC=C1)N1CCC(CC1)NC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)NCC(C1=CC=CC=C1)C1=CC=CC=C1.C(=O)[O-].[NH4+]>>C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)NC1CCNCC1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1 | c1ccc(C[N:37]2[CH2:36][CH2:35][CH:34]([NH:33][C:31]([c:30]3[n:29][c:13]([NH:14][CH2:15][CH:16]([c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[c:12]4[n:11][cH:10][n:9]([C@@H:8]5[O:7][C@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[C@@H:44]([OH:45])[C@H:42]5[OH:43])[c:41]4[n:40]3)=[O:3... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NC4CCN(Cc5ccccc5)CC4)nc32)[C@H](O)[C@@H]1O | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NC4CCNCC4)nc32)[C@H](O)[C@@H]1O | null | [OH-].[Pd+2].[OH-] | C(C)O | Deprotection | Hydrogenolysis of tertiary amines | cd3c1aa319cad45f383f17cc0b8bfc8337d7078d779f654933f9a447e64292a5 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | O=C(NC1CCNCC1)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@H]3CCCO3)c2n1 | [C:1]-[C:2]-[N;H0;D3;+0:3](-C-c1:c:c:c:c:c:1)-[C:4]-[C:5]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C:4]-[C:5] | null | [] | null | null | null | null | A solution of N-(1-benzyl-4-piperidinyl)-6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxamide (Preparation 33) (1.03 g, 1.47 mmol), palladium (II) hydroxide (0.9 g) and ammonium formate (0.46 g, 7.3 mmol) in ethanol (10 ml) was heated under re... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]CC1 | C1CCNCC1 | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1.C1CCNCC1 | Other | [OH-].[Pd+2].[OH-].C(C)O | null | null | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NC4CCN(Cc5ccccc5)CC4)nc32)[C@H](O)[C@@H]1O>[OH-].[Pd+2].[OH-].C(C)O>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NC4CCNCC4)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-642fdc49fd4040db955ddee96ee5402b | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](O)[C@@H]1O>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)O)nc32)[C@H](O)[C@@H]1O | C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)OC)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1.[OH-].[Na+].Cl>>C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)O)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1 | C[O:33][C:31]([c:30]1[n:29][c:13]([NH:14][CH2:15][CH:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:12]2[n:11][cH:10][n:9]([C@@H:8]3[O:7][C@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[C@@H:38]([OH:39])[C@H:36]3[OH:37])[c:35]2[n:34]1)=[O:32]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](O)[C@@H]1O | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)O)nc32)[C@H](O)[C@@H]1O | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(C(CNc2ncnc3c2ncn3[C@H]2CCCO2)c2ccccc2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[#7;a:6]>>[#7;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[#7;a:6] | 30.8 | [{"value": 30.0, "product": "C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)O)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 30.8, "product": "C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)O)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1", "details": "CALCUL... | null | null | null | null | A solution of methyl 6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxylate (Preparation 9) (0.7 g, 1.28 mmol) and 10% w/w aqueous sodium hydroxide solution (1.3 ml, 3.2 mmol) in methanol (2.3 ml) was stirred at room temperature for 14 hours. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1 | Other | CO | null | null | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OC)nc32)[C@H](O)[C@@H]1O>CO>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)O)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-061f27f5257242b2996f0872243ec48d | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)O)nc32)[C@H](O)[C@@H]1O.O=C(NC1CCNCC1)C(F)(F)F>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)N4CCC(NC(=O)C(F)(F)F)CC4)nc32)[C@H](O)[C@@H]1O | C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)O)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1.FC(C(=O)NC1CCNCC1)(F)F.Cl.CN(CCCN=C=NCC)C>>C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)N1CCC(CC1)NC(C(F)(F)F)=O)[C@H]1[C@@H]([C@@H]([C@H](O1)C(=O)NCC)O)O)C1=CC=CC=C1 | O[C:31]([c:30]1[n:29][c:13]([NH:14][CH2:15][CH:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:12]2[n:11][cH:10][n:9]([C@@H:8]3[O:7][C@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[C@@H:50]([OH:51])[C@H:48]3[OH:49])[c:47]2[n:46]1)=[O:32].[NH:33]1[CH2:34][CH2:35][CH:36]([NH:37][C... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)O)nc32)[C@H](O)[C@@H]1O.O=C(NC1CCNCC1)C(F)(F)F | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)N4CCC(NC(=O)C(F)(F)F)CC4)nc32)[C@H](O)[C@@H]1O | null | null | ClCCl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | fbfce93ec1ece674255bb96c5cec09ad611382b41cf117dfe580015e21744a71 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@H]3CCCO3)c2n1)N1CCCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[#7;a:4]:[c:5]:[c:6](:[#7;a:7]):[c:8](:[#7;a:9]):[#7;a:10]:1.[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]>>[#7;a:7]:[c:6]1:[c:5]:[#7;a:4]:[c:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:13](-[C:12]-[C:11])-[C:14]-[C:15]):[#7;a:10]:[c:8]:1:[#7;a:9] | null | [] | null | null | null | null | A solution of 6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxylic acid (Preparation 39) (0.2 g, 0.38 mmol), 2,2,2-trifluoro-N-(4-piperidinyl)acetamide (83 mg, 0.42 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (81 mg, 0... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1.C1CC[NH]CC1 | HO- | ClCCl | null | null | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)O)nc32)[C@H](O)[C@@H]1O.O=C(NC1CCNCC1)C(F)(F)F>ClCCl>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)N4CCC(NC(=O)C(F)(F)F)CC4)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc41c535004c441f83b6625c12376dbc | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)N4CCC(NC(=O)C(F)(F)F)CC4)nc32)[C@H](O)[C@@H]1O>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)N4CCC(N)CC4)nc32)[C@H](O)[C@@H]1O | C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)N1CCC(CC1)NC(C(F)(F)F)=O)[C@H]1[C@@H]([C@@H]([C@H](O1)C(=O)NCC)O)O)C1=CC=CC=C1>>NC1CCN(CC1)C(=O)C1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)C(=O)NCC)O)O)NCC(C1=CC=CC=C1)C1=CC=CC=C1 | O=C(C(F)(F)F)[NH:37][CH:36]1[CH2:35][CH2:34][N:33]([C:31]([c:30]2[n:29][c:13]([NH:14][CH2:15][CH:16]([c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[c:12]3[n:11][cH:10][n:9]([C@@H:8]4[O:7][C@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[C@@H:44]([OH:45])[C@H:42]4[OH:43])[c:41]3[n:40]2... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)N4CCC(NC(=O)C(F)(F)F)CC4)nc32)[C@H](O)[C@@H]1O | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)N4CCC(N)CC4)nc32)[C@H](O)[C@@H]1O | null | null | CO.N | Reduction | Hydrogenolysis of amides/imides/carbamates | 44b36597c7daf0608965c52c8db8a9220c21d9447ce54e0af375898475f3493f | caaeb83af2cb178156ae90fe7f610a106cd4bb5397d23f56d37a7fe11e2668ed | O=C(c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@H]3CCCO3)c2n1)N1CCCCC1 | F-C(-F)(-F)-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | 101.7 | [{"value": 101.7, "product": "NC1CCN(CC1)C(=O)C1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)C(=O)NCC)O)O)NCC(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (2S,3S,4R,5R)-5-[6-[(2,2-diphenylethyl)amino]-2-({4-[(trifluoroacetyl)amino]-1-piperidinyl}carbonyl)-9H-purin-9-yl]-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide (Preparation 40) (40 mg, 0.056 mmol) in methanol (1 ml) and concentrated aqueous ammonia solution (0.5 ml) was stirred at room temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Secondary amide | Primary amine | null | null | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1.C1CC[NH]CC1 | Other | CO.N | null | null | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)N4CCC(NC(=O)C(F)(F)F)CC4)nc32)[C@H](O)[C@@H]1O>CO.N>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)N4CCC(N)CC4)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ba80cd99dcf648b8a14595a793d5c94d | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(Cl)nc(N)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1.II>>CCNC(=O)C1OC(n2cnc3c(Cl)nc(I)nc32)C(OC(=O)c2ccccc2)C1OC(=O)c1ccccc1 | N(=O)OCCCC.C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C1=CC=CC=C1)=O)C(=O)NCC)N1C2=NC(=NC(=C2N=C1)Cl)N.II.ICI>>C(C1=CC=CC=C1)(=O)OC1C(OC(C1OC(C1=CC=CC=C1)=O)C(=O)NCC)N1C2=NC(=NC(=C2N=C1)Cl)I | N[c:16]1[n:15][c:13]([Cl:14])[c:12]2[n:11][cH:10][n:9]([C@@H:8]3[O:7][C@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[C@@H:30]([O:31][C:32](=[O:33])[c:34]4[cH:35][cH:36][cH:37][cH:38][cH:39]4)[C@H:20]3[O:21][C:22](=[O:23])[c:24]3[cH:25][cH:26][cH:27][cH:28][cH:29]3)[c:19]2[n:18]1.I[I:17]>>[CH3:1][CH2:2][NH:3][C:4](=[O:5])[CH... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(Cl)nc(N)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1.II | CCNC(=O)C1OC(n2cnc3c(Cl)nc(I)nc32)C(OC(=O)c2ccccc2)C1OC(=O)c1ccccc1 | null | [Cu]I | C1CCOC1 | Functional Group Interconversion | OtherReaction | f2bfbdf2f4ec84bc795fc5810844800ef4e28ee754bf1d46d7f44827ba3d48eb | 9c224743a26d9e1c3135e4817dd611aec414d8ea156f02200a3aef865be78b01 | O=C(OC1COC(n2cnc3cncnc32)C1OC(=O)c1ccccc1)c1ccccc1 | I-[I;H0;D1;+0:1].N-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8](-[C:9]-[#8:10]):[c:11]:2:[#7;a:12]:1>>[#8:10]-[C:9]-[#7;a:8]1:[c:7]:[#7;a:6]:[c:5]2:[c:4]:[#7;a:3]:[c;H0;D3;+0:2](-[I;H0;D1;+0:1]):[#7;a:12]:[c:11]:1:2 | 78 | [{"value": 78.0, "product": "C(C1=CC=CC=C1)(=O)OC1C(OC(C1OC(C1=CC=CC=C1)=O)C(=O)NCC)N1C2=NC(=NC(=C2N=C1)Cl)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.6, "product": "C(C1=CC=CC=C1)(=O)OC1C(OC(C1OC(C1=CC=CC=C1)=O)C(=O)NCC)N1C2=NC(=NC(=C2N=C1)Cl)I", "details": "CALCULATEDPERCENTYIELD", "is_desired":... | null | null | null | null | n-Butyl nitrite (4.65 ml, 39.7 mmol) was added to a suspension of (2R,3R,4S,5S)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-(benzoyloxy)-5-[(ethylamino)carbonyl]-tetrahydro-3-furanyl benzoate (Preparation 46) (8.10 g, 14.7 mmol), iodine (3.73 g, 14.7 mmol), copper(1) iodide (6.16 g, 32.3 mmol) and diiodomethane (12.55 ml, 155... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Aromatic halide | c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | C1CCOC1.c1ncc2nc[nH]c2n1.c1ccccc1.c1ccccc1 | HI | [Cu]I.C1CCOC1 | null | null | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(Cl)nc(N)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1.II>[Cu]I.C1CCOC1>CCNC(=O)C1OC(n2cnc3c(Cl)nc(I)nc32)C(OC(=O)c2ccccc2)C1OC(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-66fb887f20564c55b3dca39be042d84e | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(Cl)nc(I)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1.Cc1cccc(C(CN)c2cccc(C)c2)c1>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4cccc(C)c4)c4cccc(C)c4)nc(I)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1 | C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C1=CC=CC=C1)=O)C(=O)NCC)N1C2=NC(=NC(=C2N=C1)Cl)I.CC=1C=C(C=CC1)C(CN)C1=CC(=CC=C1)C>>C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C1=CC=CC=C1)=O)C(=O)NCC)N1C2=NC(=NC(=C2N=C1)NCC(C1=CC(=CC=C1)C)C1=CC(=CC=C1)C)I | Cl[c:13]1[c:12]2[n:11][cH:10][n:9]([C@@H:8]3[O:7][C@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[C@@H:46]([O:47][C:48](=[O:49])[c:50]4[cH:51][cH:52][cH:53][cH:54][cH:55]4)[C@H:36]3[O:37][C:38](=[O:39])[c:40]3[cH:41][cH:42][cH:43][cH:44][cH:45]3)[c:35]2[n:34][c:32]([I:33])[n:31]1.[NH2:14][CH2:15][CH:16]([c:17]1[cH:18][cH:19]... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(Cl)nc(I)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1.Cc1cccc(C(CN)c2cccc(C)c2)c1 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4cccc(C)c4)c4cccc(C)c4)nc(I)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1 | null | null | C(C)(C)O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | d29b1bab4afefe0db66c5d87d4d37a8be0c49cfdb04c6c8844dee54b4b5d425a | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(O[C@H]1[C@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)ncnc32)OC[C@H]1OC(=O)c1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[I;D1;H0:4]):[#7;a:5]:[c:6]2:[#7;a:7](-[C:8]-[#8:9]):[c:10]:[#7;a:11]:[c:12]:2:1.[C:13]-[C:14]-[NH2;D1;+0:15]>>[#8:9]-[C:8]-[#7;a:7]1:[c:10]:[#7;a:11]:[c:12]2:[c:6]:1:[#7;a:5]:[c:3](-[I;D1;H0:4]):[#7;a:2]:[c;H0;D3;+0:1]:2-[NH;D2;+0:15]-[C:14]-[C:13] | 87 | [{"value": 87.0, "product": "C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C1=CC=CC=C1)=O)C(=O)NCC)N1C2=NC(=NC(=C2N=C1)NCC(C1=CC(=CC=C1)C)C1=CC(=CC=C1)C)I", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.5, "product": "C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C1=CC=CC=C1)=O)C(=O)NCC)N1C2=NC(=N... | null | null | null | null | A solution of ((2R,3R,4S,5S)-4-(benzoyloxy)-2-(6-chloro-2-iodo-9H-purin-9-yl)-5-[(ethylamino)carbonyl]-tetrahydro-3-furanyl benzoate (Preparation 47) (0.6 g, 0.91 mmol) and 2,2-bis(3-methylphenyl)ethylamine (0.3 g, 1.36 mmol) in isopropanol (20 ml) was stirred at room temperature for 48 hours. Solvent was removed under... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1.c1ccccc1.c1ccccc1 | HCl | C(C)(C)O | null | null | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(Cl)nc(I)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1.Cc1cccc(C(CN)c2cccc(C)c2)c1>C(C)(C)O>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4cccc(C)c4)c4cccc(C)c4)nc(I)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-86a4871f3cc54886bc9591203388cc9b | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(Cl)nc(I)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1.NCC(c1cccc(Cl)c1)c1cccc(Cl)c1>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4cccc(Cl)c4)c4cccc(Cl)c4)nc(I)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1 | C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C1=CC=CC=C1)=O)C(=O)NCC)N1C2=NC(=NC(=C2N=C1)Cl)I.ClC=1C=C(C=CC1)C(CN)C1=CC(=CC=C1)Cl>>C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C1=CC=CC=C1)=O)C(=O)NCC)N1C2=NC(=NC(=C2N=C1)NCC(C1=CC(=CC=C1)Cl)C1=CC(=CC=C1)Cl)I | Cl[c:13]1[c:12]2[n:11][cH:10][n:9]([C@@H:8]3[O:7][C@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[C@@H:46]([O:47][C:48](=[O:49])[c:50]4[cH:51][cH:52][cH:53][cH:54][cH:55]4)[C@H:36]3[O:37][C:38](=[O:39])[c:40]3[cH:41][cH:42][cH:43][cH:44][cH:45]3)[c:35]2[n:34][c:32]([I:33])[n:31]1.[NH2:14][CH2:15][CH:16]([c:17]1[cH:18][cH:19]... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(Cl)nc(I)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1.NCC(c1cccc(Cl)c1)c1cccc(Cl)c1 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4cccc(Cl)c4)c4cccc(Cl)c4)nc(I)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | d29b1bab4afefe0db66c5d87d4d37a8be0c49cfdb04c6c8844dee54b4b5d425a | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | O=C(O[C@H]1[C@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)ncnc32)OC[C@H]1OC(=O)c1ccccc1)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[I;D1;H0:4]):[#7;a:5]:[c:6]2:[#7;a:7](-[C:8]-[#8:9]):[c:10]:[#7;a:11]:[c:12]:2:1.[C:13]-[C:14]-[NH2;D1;+0:15]>>[#8:9]-[C:8]-[#7;a:7]1:[c:10]:[#7;a:11]:[c:12]2:[c:6]:1:[#7;a:5]:[c:3](-[I;D1;H0:4]):[#7;a:2]:[c;H0;D3;+0:1]:2-[NH;D2;+0:15]-[C:14]-[C:13] | null | [] | null | null | null | null | Prepared from ((2R,3R,4S,5S)-4-(benzoyloxy)-2-(6-chloro-2-iodo-9H-purin-9-yl)-5-[(ethylamino)carbonyl]-tetrahydro-3-furanyl benzoate (Preparation 47) and 2,2-bis(3-chlorophenyl)ethylamine by the same method as Preparation 48. The title compound was obtained as a yellow foam.
Conditions: See reaction.notes.procedure_det... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2[nH]cnc2n1 | c1ncc2nc[nH]c2n1 | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1.c1ccccc1.c1ccccc1 | HCl | null | null | null | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(Cl)nc(I)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1.NCC(c1cccc(Cl)c1)c1cccc(Cl)c1>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4cccc(Cl)c4)c4cccc(Cl)c4)nc(I)nc32)[C@H](OC(=O)c2ccccc2)[C@@H]1OC(=O)c1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1eb4ad4101bd408cab4df1eea911d020 | CC(C)N(CCNC(=O)n1ccnc1)C(C)C.NCCNC(=O)OCc1ccccc1>>CC(C)N(CCNC(=O)NCCNC(=O)OCc1ccccc1)C(C)C | Cl.NCCNC(OCC1=CC=CC=C1)=O.C(C)(C)N(CCNC(=O)N1C=NC=C1)C(C)C.C(C)N(CC)CC>>C(C)(C)N(CCNC(=O)NCCNC(OCC1=CC=CC=C1)=O)C(C)C | c1cn([C:8]([NH:7][CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH:24]([CH3:25])[CH3:26])=[O:9])cn1.[NH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][NH:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][NH:13][C:14](=[O:15])[O:16][CH2:1... | CC(C)N(CCNC(=O)n1ccnc1)C(C)C.NCCNC(=O)OCc1ccccc1 | CC(C)N(CCNC(=O)NCCNC(=O)OCc1ccccc1)C(C)C | null | null | ClCCl | Acylation | OtherReaction | 2fca1e60b30bb25dd42d9c3a0a409c10e22201738c1a0d1497c17610c9a7f90b | 11d83d172c98dee16e5582fbe84e86af1814ed957a762275a38224e82e89f00a | c1ccccc1 | [C:1]-[#7:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-n1:c:c:n:c:1.[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#7:2]-[C:1] | 109.6 | [{"value": 109.6, "product": "C(C)(C)N(CCNC(=O)NCCNC(OCC1=CC=CC=C1)=O)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of benzyl 2-aminoethylcarbamate hydrochloride (4.33 g, 18.8 mmol), N-[2-(diisopropylamino)ethyl]-1H-imidazole-1-carboxamide (Preparation 19) (3.73 g, 15.64 mmol) and triethylamine (2.62 ml, 18.8 mmol) in dichloromethane (100 ml) was heated under reflux for 14 hours. The solution was allowed to cool to room t... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | Urea | c1c[nH]cn1 | null | c1ccccc1 | Other | ClCCl | null | null | CC(C)N(CCNC(=O)n1ccnc1)C(C)C.NCCNC(=O)OCc1ccccc1>ClCCl>CC(C)N(CCNC(=O)NCCNC(=O)OCc1ccccc1)C(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a9cf39217da648449b967ed86fbe87b0 | NCCNC(=O)OCc1ccccc1.O=C(NCCN1CCCCC1)n1ccnc1>>O=C(NCCNC(=O)OCc1ccccc1)NCCN1CCCCC1 | Cl.NCCNC(OCC1=CC=CC=C1)=O.N1(CCCCC1)CCNC(=O)N1C=NC=C1>>N1(CCCCC1)CCNC(=O)NCCNC(OCC1=CC=CC=C1)=O | [NH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:8])[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.c1cn([C:2](=[O:1])[NH:17][CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)cn1>>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][NH:6][C:7](=[O:8])[O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[NH:17][CH2:18][CH2:... | NCCNC(=O)OCc1ccccc1.O=C(NCCN1CCCCC1)n1ccnc1 | O=C(NCCNC(=O)OCc1ccccc1)NCCN1CCCCC1 | null | null | null | Acylation | OtherReaction | 2fca1e60b30bb25dd42d9c3a0a409c10e22201738c1a0d1497c17610c9a7f90b | 11d83d172c98dee16e5582fbe84e86af1814ed957a762275a38224e82e89f00a | O=C(NCCNC(=O)OCc1ccccc1)NCCN1CCCCC1 | [C:1]-[#7:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-n1:c:c:n:c:1.[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:1]-[#7:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[NH;D2;+0:7]-[C:6]-[C:5] | null | [] | null | null | null | null | Prepared from benzyl 2-aminoethylcarbamate hydrochloride and N-[2-(1-piperidinyl)ethyl]-1H-imidazole-1-carboxamide (Preparation 18) by a similar procedure to Preparation 50. The title compound was obtained as a yellow oil.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | Urea | c1c[nH]cn1 | null | c1ccccc1.C1CC[NH]CC1 | Other | null | null | null | NCCNC(=O)OCc1ccccc1.O=C(NCCN1CCCCC1)n1ccnc1>>O=C(NCCNC(=O)OCc1ccccc1)NCCN1CCCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a6dcdf464c440f5b2372f95897642bd | CC(C)N(CCNC(=O)NCCNC(=O)OCc1ccccc1)C(C)C>>CC(C)N(CCNC(=O)NCCN)C(C)C.N | C(C)(C)N(CCNC(=O)NCCNC(OCC1=CC=CC=C1)=O)C(C)C>>N.NCCNC(=O)NCCN(C(C)C)C(C)C | O=C(OCc1ccccc1)[NH:13][CH2:12][CH2:11][NH:10][C:8]([NH:7][CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[CH:14]([CH3:15])[CH3:16])=[O:9]>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][NH:7][C:8](=[O:9])[NH:10][CH2:11][CH2:12][NH2:13])[CH:14]([CH3:15])[CH3:16].[NH3:17] | CC(C)N(CCNC(=O)NCCNC(=O)OCc1ccccc1)C(C)C | CC(C)N(CCNC(=O)NCCN)C(C)C.N | null | [OH-].[Pd+2].[OH-] | C(C)O | Miscellaneous | Hydrogenolysis of amides/imides/carbamates | 8432fba507068d7cbb736b1152500b311a95cf832573d00d78ba81d73ce8e2b1 | 70d56c35a1f2712eddb71d4ede83e11ec1c1a0860c8c4220cbdc53cc816a7d45 | null | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 216.3 | [{"value": 216.3, "product": "NCCNC(=O)NCCN(C(C)C)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of benzyl 2-[({[2-(diisopropylamino)ethyl]amino}carbonyl)amino]ethylcarbamate (Preparation 50) (6.25 g, 14.45 mmol) in ethanol (100 ml) was hydrogenated at room temperature over palladium (II) hydroxide (250 mg) for 4 hours at 414 KPa. The catalyst was removed by filtration through Arbocel (trade mark) and s... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | null | HO- | [OH-].[Pd+2].[OH-].C(C)O | null | null | CC(C)N(CCNC(=O)NCCNC(=O)OCc1ccccc1)C(C)C>[OH-].[Pd+2].[OH-].C(C)O>CC(C)N(CCNC(=O)NCCN)C(C)C.N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ea1168c8fcc44c3d867e3ceb3fe2d073 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O.O=C(OCc1ccccc1)c1ccc(CNC(=O)n2ccnc2)cc1>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCc4ccc(C(=O)OCc5ccccc5)cc4)nc32)[C@H](O)[C@@H]1O | NCCNC(=O)C1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)NCC(C1=CC=CC=C1)C1=CC=CC=C1.N1(C=NC=C1)C(=O)NCC1=CC=C(C(=O)OCC2=CC=CC=C2)C=C1>>C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)NCCNC(=O)NCC1=CC=C(C(=O)OCC2=CC=CC=C2)C=C1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC)C1=CC=CC=C1 | [CH3:1][CH2:2][NH:3][C:4](=[O:5])[C@H:6]1[O:7][C@@H:8]([n:9]2[cH:10][n:11][c:12]3[c:13]([NH:14][CH2:15][CH:16]([c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[n:29][c:30]([C:31](=[O:32])[NH:33][CH2:34][CH2:35][NH2:36])[n:57][c:58]23)[C@H:59]([OH:60])[C@@H:61]1[OH:62].c1cn([C:37]... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O.O=C(OCc1ccccc1)c1ccc(CNC(=O)n2ccnc2)cc1 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCc4ccc(C(=O)OCc5ccccc5)cc4)nc32)[C@H](O)[C@@H]1O | null | null | null | Acylation | OtherReaction | 2fca1e60b30bb25dd42d9c3a0a409c10e22201738c1a0d1497c17610c9a7f90b | 11d83d172c98dee16e5582fbe84e86af1814ed957a762275a38224e82e89f00a | O=C(NCCNC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@H]3CCCO3)c2n1)NCc1ccc(C(=O)OCc2ccccc2)cc1 | [C:1]-[#7:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-n1:c:c:n:c:1.[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[#7:2]-[C:1] | null | [] | null | null | null | null | Prepared from N-(2-aminoethyl)-6-[(2,2-diphenylethyl)amino]-9-{(2R,3R,4S,5S)-5-[(ethylamino)carbonyl]-3,4-dihydroxytetrahydro-2-furanyl}-9H-purine-2-carboxamide (Preparation 10) and benzyl 4-{[(1H-imidazol-1-ylcarbonyl)amino]methyl}benzoate (Preparation 54) by a similar method to Example 1. The target compound was obta... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | Urea | c1c[nH]cn1 | null | C1CCOC1.c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1.c1ccccc1.c1ccccc1 | Other | null | null | null | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCN)nc32)[C@H](O)[C@@H]1O.O=C(OCc1ccccc1)c1ccc(CNC(=O)n2ccnc2)cc1>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)NCCNC(=O)NCc4ccc(C(=O)OCc5ccccc5)cc4)nc32)[C@H](O)[C@@H]1O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-511b94495bbc4410b949c19d4a59e5c2 | CCO.Clc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1>>CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 | C(C)O.ClC1=NC(=C2N=CN(C2=N1)C1OCCCC1)NCC(C1=CC=CC=C1)C1=CC=CC=C1.C(C)O.C([O-])([O-])=O.[Na+].[Na+]>>C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)OCC)C1OCCCC1)C1=CC=CC=C1 | [CH3:1][CH2:2][OH:3].Cl[c:6]1[n:7][c:8]([NH:9][CH2:10][CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[c:24]2[n:25][cH:26][n:27]([CH:28]3[CH2:29][CH2:30][CH2:31][CH2:32][O:33]3)[c:34]2[n:35]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([NH:9][CH2:10][CH:11]([c:12]2[... | CCO.Clc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 | CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 | null | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2] | null | Acylation | OtherReaction | 82ad05ac461299fab6df2807d08ffbf3c3ee8a6a8331beed81410054880ae078 | cb2457ddc31be6a34efcab473e76115982b4ecde38288b80cb0e3a124b5c7fdd | c1ccc(C(CNc2ncnc3c2ncn3C2CCCCO2)c2ccccc2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]-[#8:6]):[c:7]:[#7;a:8]:[c:9]:2:[c:10]:[#7;a:11]:1.[C;D1;H3:12]-[C:13]-[OH;D1;+0:14]>>[#8:6]-[C:5]-[#7;a:4]1:[c:7]:[#7;a:8]:[c:9]2:[c:10]:[#7;a:11]:[c;H0;D3;+0:1](-[C:15](=[O;D1;H0:16])-[O;H0;D2;+0:14]-[C:13]-[C;D1;H3:12]):[#7;a:2]:[c:3]:1:2 | null | [] | 60 | CELSIUS | 10 | HOUR | To a suspension of palladium (II) acetate (1.50 g, 0.00668 moles) in absolute ethanol (1000 ml) was added 1,1′-bis(diphenylphosphino)ferrocene (7.00 g, 0.0126 moles) and the resultant suspension was stirred under an atmosphere of nitrogen for 18 hours to give the catalyst mixture. To a mixture of 2-chloro-N-(2,2-diphen... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ester | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ccccc1.c1ccccc1.c1ncc2[nH]cnc2n1.C1CCOCC1 | HCl | C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2] | 60 | 10 | CCO.Clc1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1>C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2]>CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-81c01a4908cd47028c7b6659b5d734b4 | CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1>>CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1 | C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)OCC)C1OCCCC1)C1=CC=CC=C1.FC(C(=O)O)(F)F>>C1(=CC=CC=C1)C(CNC1=C2N=CNC2=NC(=N1)C(=O)OCC)C1=CC=CC=C1 | C1CCC([n:27]2[cH:26][n:25][c:24]3[c:8]([NH:9][CH2:10][CH:11]([c:12]4[cH:13][cH:14][cH:15][cH:16][cH:17]4)[c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[n:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:29][c:28]32)OC1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([NH:9][CH2:10][CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][... | CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1 | CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1 | null | null | C(C)O | Reduction | OtherReaction | 5884540ddb12ce381424fd4d8168e9c573ef97adf4e044c59506f6d05225a030 | 84394d34c591024a84d9393eb3e8adb8ada5a6225c3abafc4dae9aedd4568be4 | c1ccc(C(CNc2ncnc3[nH]cnc23)c2ccccc2)cc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]2:[c:7](:[#7;a:8]:[c:9]:[n;H0;D3;+0:10]:2-C2-C-C-C-C-O-2):[c:11]:[#7;a:12]:1>>[#8:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[c:6]2:[nH;D2;+0:10]:[c:9]:[#7;a:8]:[c:7]:2:[c:11]:[#7;a:12]:1 | 100.6 | [{"value": 100.6, "product": "C1(=CC=CC=C1)C(CNC1=C2N=CNC2=NC(=N1)C(=O)OCC)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of ethyl 6-[(2,2-diphenylethyl)amino]-9-(tetrahydro-2H-pyran-2-yl)-9H-purine-2-carboxylate (Preparation 62) (250 g, 0.530 moles) in absolute ethanol (1250 ml) under an atmosphere of nitrogen was added trifluoroacetic acid (73.5 g, 0.645 moles) and the resultant mixture was heated at 50° C. for 20 hours.... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | C1CCOCC1.c1ncc2nc[nH]c2n1 | c1ncc2[nH]cnc2n1 | c1ccccc1.c1ccccc1.c1ncc2[nH]cnc2n1 | HO- | C(C)O | null | null | CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn(C3CCCCO3)c2n1>C(C)O>CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-24077634027d402792edb18726eda7e5 | CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O.CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1>>CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]3OC(C)=O)c2n1 | FC(S(=O)(=O)O[Si](C)(C)C)(F)F.C(C)(=O)O[C@H]1[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O.C([O-])(O)=O.[Na+].CN1CCOCC1.C1(=CC=CC=C1)C(CNC1=C2N=CNC2=NC(=N1)C(=O)OCC)C1=CC=CC=C1>>C(C)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C)=O)COC(C)=O)N1C2=NC(=NC(=C2N=C1)NCC(C1=CC=CC=C1)C1=CC=CC=C1)C(=O)OCC | CC(=O)O[C@@H:28]1[O:29][C@H:30]([CH2:31][O:32][C:33]([CH3:34])=[O:35])[C@@H:36]([O:37][C:38]([CH3:39])=[O:40])[C@H:41]1[O:42][C:43]([CH3:44])=[O:45].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([NH:9][CH2:10][CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[c:24]2[n:25... | CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O.CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1 | CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]3OC(C)=O)c2n1 | null | null | C(C)(=O)OCC.COCCOC | Heteroatom Alkylation and Arylation | OtherReaction | a90222e67a4a22678b87b59d1ecec052c8245214c445cc6a40c830f6056425a0 | 555d70919b361b350c80f46e885ff5cda87616c212c907f1056db36bb1eb2375 | c1ccc(C(CNc2ncnc3c2ncn3[C@H]2CCCO2)c2ccccc2)cc1 | C-C(=O)-O-[C@@H;D3;+0:1]1-[#8:2]-[C:3]-[C:4]-[C:5]-1-[#8:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9].[#8:10]-[C:11](=[O;D1;H0:12])-[c:13]1:[#7;a:14]:[c:15]2:[nH;D2;+0:16]:[c:17]:[#7;a:18]:[c:19]:2:[c:20]:[#7;a:21]:1>>[#8:10]-[C:11](=[O;D1;H0:12])-[c:13]1:[#7;a:14]:[c:15]2:[c:19](:[#7;a:18]:[c:17]:[n;H0;D3;+0:16]:2-[C@@H;D3;+0:1... | null | [] | 55 | CELSIUS | null | null | To a suspension of ethyl 6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate (Preparation 63) (40.0 g, 0.103 moles) in anhydrous 1,2-dimethoxyethane (240 ml) under an atmosphere of nitrogen was added 4-methylmorpholine (11.5 g, 12.5 ml, 0.114 moles) and the resultant mixture was heated to 45° C. with stirring. To this... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Ether | C1CCOC1.c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1CCOC1 | c1ccccc1.c1ccccc1.c1ncc2[nH]cnc2n1.C1CCOC1 | HO- | C(C)(=O)OCC.COCCOC | 55 | null | CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O.CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2nc[nH]c2n1>C(C)(=O)OCC.COCCOC>CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]3OC(C)=O)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f2a6a459e69e4f6da6d4623423fcd8a8 | CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]3OC(C)=O)c2n1>>CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1 | C(C)(=O)O.C(C)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]1OC(C)=O)COC(C)=O)N1C2=NC(=NC(=C2N=C1)NCC(C1=CC=CC=C1)C1=CC=CC=C1)C(=O)OCC.[O-]CC.[Na+]>>O[C@H]1[C@@H](O[C@@H]([C@H]1O)CO)N1C2=NC(=NC(=C2N=C1)NCC(C1=CC=CC=C1)C1=CC=CC=C1)C(=O)OCC | CC(=O)[O:32][CH2:31][C@H:30]1[O:29][C@@H:28]([n:27]2[cH:26][n:25][c:24]3[c:8]([NH:9][CH2:10][CH:11]([c:12]4[cH:13][cH:14][cH:15][cH:16][cH:17]4)[c:18]4[cH:19][cH:20][cH:21][cH:22][cH:23]4)[n:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[n:38][c:37]32)[C@H:35]([O:36]C(C)=O)[C@@H:33]1[O:34]C(C)=O>>[CH3:1][CH2:2][O:3][C:4](=[... | CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]3OC(C)=O)c2n1 | CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1 | null | null | C(C)O | Reduction | OtherReaction | b1205f31a625dd524c4abcf6ea407c1a38966308677d8535d59411f69b7afe49 | 53784a05a6c1858c11deb702d4a1392e7852c783da9a57d4771755f87682c932 | c1ccc(C(CNc2ncnc3c2ncn3[C@H]2CCCO2)c2ccccc2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]1-[#8:4]-[C:5]-[C:6](-[O;H0;D2;+0:7]-C(-C)=O)-[C:8]-1-[O;H0;D2;+0:9]-C(-C)=O>>[OH;D1;+0:1]-[C:2]-[C:3]1-[#8:4]-[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]-1-[OH;D1;+0:9] | null | [] | null | null | null | null | To a solution of crude ethyl 9-{(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-[(acetyloxy)methyl]tetrahydro-2-furanyl}-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate (Preparation 64) (74.9 g, assumed 0.103 moles) in warm absolute ethanol (330 ml) was added sodium ethoxide (1.2 g, 0.018 moles) in portions over 23 hours. The ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester.Ester | Primary alcohol.Secondary alcohol.Secondary alcohol | null | null | c1ccccc1.c1ccccc1.c1ncc2[nH]cnc2n1.C1CCOC1 | HO- | C(C)O | null | null | CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H]3OC(C)=O)c2n1>C(C)O>CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c861fea8709446249bd3147edec32b75 | CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](CO)[C@H]4OC(C)(C)O[C@H]43)c2n1>>CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](C(=O)O)[C@H]4OC(C)(C)O[C@H]43)c2n1 | Cl.OC[C@H]1O[C@H]([C@H]2[C@@H]1OC(O2)(C)C)N2C1=NC(=NC(=C1N=C2)NCC(C2=CC=CC=C2)C2=CC=CC=C2)C(=O)OCC.P(=O)(O)(O)[O-].[Na+].Cl(=O)[O-].[Na+].S(=O)([O-])[O-].[Na+].[Na+]>>C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)OCC)[C@@H]1O[C@@H]([C@@H]2[C@H]1OC(O2)(C)C)C(=O)O)C2=CC=CC=C2 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][c:8]([NH:9][CH2:10][CH:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[c:24]2[n:25][cH:26][n:27]([C@@H:28]3[O:29][C@H:30]([CH2:31][OH:33])[C@H:34]4[O:35][C:36]([CH3:37])([CH3:38])[O:39][C@@H:40]34)[c:41]2[n:42]1>>[CH3:1][CH2:2][O:3... | CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](CO)[C@H]4OC(C)(C)O[C@H]43)c2n1 | CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](C(=O)O)[C@H]4OC(C)(C)O[C@H]43)c2n1 | null | Cl[O-].[Na+] | O.C(C)#N | Oxidation | Oxidation of alcohol to carboxylic acid | b709baac44a995a9a8f6386a6b5d87f98c32eb5a0636340abc1f778fae827230 | 4454822e22dc2dc24e7495385256bfce456e337c240bb764261f81dbeda1aaa1 | c1ccc(C(CNc2ncnc3c2ncn3[C@@H]2OC[C@H]3OCO[C@@H]23)c2ccccc2)cc1 | [#8:1]-[C:2]-[C:3](-[CH2;D2;+0:4]-[O;D1;H1:5])-[#8:6]-[C:7]>>[#8:1]-[C:2]-[C:3](-[C;H0;D3;+0:4](=[O;D1;H0:8])-[O;D1;H1:5])-[#8:6]-[C:7] | null | [] | null | null | 18 | HOUR | To a solution of ethyl 9-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate (Preparation 66) (15.4 g, 0.0276 moles) in acetonitrile under an atmosphere of nitrogen was added 2,2,6,6-tetramethylpiperidinyl-1-oxy, free radical (0.30 g... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ncc2[nH]cnc2n1.C1O[C@H]2COC[C@H]2O1 | Other | Cl[O-].[Na+].O.C(C)#N | null | 18 | CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](CO)[C@H]4OC(C)(C)O[C@H]43)c2n1>Cl[O-].[Na+].O.C(C)#N>CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](C(=O)O)[C@H]4OC(C)(C)O[C@H]43)c2n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-347e3b4fbd954295861786e00cfc0e34 | CCN.CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](C(=O)O)[C@H]4OC(C)(C)O[C@H]43)c2n1>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OCC)nc32)[C@@H]2OC(C)(C)O[C@@H]21 | C(C)N.C1(=CC=CC=C1)C(CNC1=C2N=CN(C2=NC(=N1)C(=O)OCC)[C@@H]1O[C@@H]([C@@H]2[C@H]1OC(O2)(C)C)C(=O)O)C2=CC=CC=C2.C(=O)(N1C=NC=C1)N1C=NC=C1.C(C)N.O>>C(C)NC(=O)[C@H]1O[C@H]([C@H]2[C@@H]1OC(O2)(C)C)N2C1=NC(=NC(=C1N=C2)NCC(C2=CC=CC=C2)C2=CC=CC=C2)C(=O)OCC | [CH3:1][CH2:2][NH2:3].O[C:4](=[O:5])[C@H:6]1[O:7][C@@H:8]([n:9]2[cH:10][n:11][c:12]3[c:13]([NH:14][CH2:15][CH:16]([c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[n:29][c:30]([C:31](=[O:32])[O:33][CH2:34][CH3:35])[n:36][c:37]23)[C@@H:38]2[O:39][C:40]([CH3:41])([CH3:42])[O:43][C@H... | CCN.CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](C(=O)O)[C@H]4OC(C)(C)O[C@H]43)c2n1 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OCC)nc32)[C@@H]2OC(C)(C)O[C@@H]21 | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccc(C(CNc2ncnc3c2ncn3[C@@H]2OC[C@H]3OCO[C@@H]23)c2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[#8:4]-[C:5])-[C:6]-[#8:7].[C;D1;H3:8]-[C:9]-[NH2;D1;+0:10]>>[#8:7]-[C:6]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:10]-[C:9]-[C;D1;H3:8])-[#8:4]-[C:5] | 78.9 | [{"value": 78.9, "product": "C(C)NC(=O)[C@H]1O[C@H]([C@H]2[C@@H]1OC(O2)(C)C)N2C1=NC(=NC(=C1N=C2)NCC(C2=CC=CC=C2)C2=CC=CC=C2)C(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 15 | CELSIUS | 2 | HOUR | To a solution of (3aS,4S,6R,6aR)-6-[6-[(2,2-diphenylethyl)amino]-2-(ethoxycarbonyl)-9H-purin-9-yl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid (Preparations 67 and 68) (20.0 g, 0.0349 moles) in anhydrous tetrahydrofuran (100 ml) under an atmosphere of nitrogen was added 1,1′-carbonyldiimidazole (6.8... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1.C1O[C@H]2COC[C@H]2O1 | HO- | O1CCCC1 | 15 | 2 | CCN.CCOC(=O)c1nc(NCC(c2ccccc2)c2ccccc2)c2ncn([C@@H]3O[C@H](C(=O)O)[C@H]4OC(C)(C)O[C@H]43)c2n1>O1CCCC1>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OCC)nc32)[C@@H]2OC(C)(C)O[C@@H]21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-11f81d031b174a5a8daa77a49c922b63 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OCC)nc32)[C@@H]2OC(C)(C)O[C@@H]21>>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)O)nc32)[C@@H]2OC(C)(C)O[C@@H]21 | C(C)NC(=O)[C@H]1O[C@H]([C@H]2[C@@H]1OC(O2)(C)C)N2C1=NC(=NC(=C1N=C2)NCC(C2=CC=CC=C2)C2=CC=CC=C2)C(=O)OCC.[OH-].[Na+]>>C(C)NC(=O)[C@H]1O[C@H]([C@H]2[C@@H]1OC(O2)(C)C)N2C1=NC(=NC(=C1N=C2)NCC(C2=CC=CC=C2)C2=CC=CC=C2)C(=O)O | CC[O:33][C:31]([c:30]1[n:29][c:13]([NH:14][CH2:15][CH:16]([c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:23]2[cH:24][cH:25][cH:26][cH:27][cH:28]2)[c:12]2[n:11][cH:10][n:9]([C@@H:8]3[O:7][C@H:6]([C:4]([NH:3][CH2:2][CH3:1])=[O:5])[C@@H:42]4[C@H:36]3[O:37][C:38]([CH3:39])([CH3:40])[O:41]4)[c:35]2[n:34]1)=[O:32]>>[CH3:1][C... | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OCC)nc32)[C@@H]2OC(C)(C)O[C@@H]21 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)O)nc32)[C@@H]2OC(C)(C)O[C@@H]21 | null | null | CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(C(CNc2ncnc3c2ncn3[C@@H]2OC[C@H]3OCO[C@@H]23)c2ccccc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4](:[#7;a:5]):[#7;a:6]>>[#7;a:5]:[c:4](-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1]):[#7;a:6] | 98.8 | [{"value": 98.8, "product": "C(C)NC(=O)[C@H]1O[C@H]([C@H]2[C@@H]1OC(O2)(C)C)N2C1=NC(=NC(=C1N=C2)NCC(C2=CC=CC=C2)C2=CC=CC=C2)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a solution of ethyl 9-{(3aR,4R,6S,6aS)-6-[(ethylamino)carbonyl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-6-[(2,2-diphenylethyl)amino]-9H-purine-2-carboxylate (Preparation 69) (16.47 g, 0.0274 moles) in methanol (164 ml) was added aqueous sodium hydroxide (30.2 ml of a 1 M solution, 0.0302 moles) and the re... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccccc1.c1ncc2nc[nH]c2n1.C1O[C@H]2COC[C@H]2O1 | Other | CO | null | 1.5 | CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)OCC)nc32)[C@@H]2OC(C)(C)O[C@@H]21>CO>CCNC(=O)[C@H]1O[C@@H](n2cnc3c(NCC(c4ccccc4)c4ccccc4)nc(C(=O)O)nc32)[C@@H]2OC(C)(C)O[C@@H]21 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9de8626dfbfe4853a1c297e1bbb92197 | CC(C)(C)OC(=O)NCCN.NC1CCN(c2ccccn2)CC1.O=C(n1ccnc1)n1ccnc1>>CC(C)(C)OC(=O)NCCNC(=O)NC1CCN(c2ccccn2)CC1 | NCCNC(OC(C)(C)C)=O.Cl.Cl.N1=C(C=CC=C1)N1CCC(CC1)N.C(=O)(N1C=NC=C1)N1C=NC=C1.C(C)(C)N(C(C)C)CC>>N1=C(C=CC=C1)N1CCC(CC1)NC(=O)NCCNC(OC(C)(C)C)=O | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][NH2:11].[NH2:14][CH:15]1[CH2:16][CH2:17][N:18]([c:19]2[cH:20][cH:21][cH:22][cH:23][n:24]2)[CH2:25][CH2:26]1.c1cn([C:12](n2ccnc2)=[O:13])cn1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:13])[NH:14][CH:15]1[CH... | CC(C)(C)OC(=O)NCCN.NC1CCN(c2ccccn2)CC1.O=C(n1ccnc1)n1ccnc1 | CC(C)(C)OC(=O)NCCNC(=O)NC1CCN(c2ccccn2)CC1 | null | null | C(C)#N | Acylation | OtherReaction | 4bbb31b0118d7292be8236579c179606942bc7ed40684e26f7727a569ab5c30d | 4ff96020857e85930fbee987c7fa4ef615e45b2ea39cff27ceaec8f9174d5b6f | c1ccc(N2CCCCC2)nc1 | [C:1]-[C:2](-[NH2;D1;+0:3])-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7].[O;D1;H0:8]=[C;H0;D3;+0:9](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[C:2](-[NH;D2;+0:3]-[C;H0;D3;+0:9](=[O;D1;H0:8])-[NH;D2;+0:7]-[C:6]-[C:5])-[C:4] | null | [] | null | null | 20 | MINUTE | an ice-cooled solution of 1-(2-pyridinyl)-4-piperidinylamine dihydrochloride EP-A-0021973) (20.82 g, 0.0832 moles) and 1,1′-carbonyldiimidazole (14.85 g, 0.915 moles) in acetonitrile (140 ml) under an atmosphere of nitrogen was added N,N-di-iso-propylethylamine (22.0 g, 29.7 ml, 0.170 moles) over a period of 20 minutes... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine | Urea | c1c[nH]cn1.c1c[nH]cn1 | null | C1CC[NH]CC1.c1ccncc1 | Other | C(C)#N | null | 0.333333 | CC(C)(C)OC(=O)NCCN.NC1CCN(c2ccccn2)CC1.O=C(n1ccnc1)n1ccnc1>C(C)#N>CC(C)(C)OC(=O)NCCNC(=O)NC1CCN(c2ccccn2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1867737373ad4bb48701270e5edc5939 | Cc1cc(C)c(S(=O)(=O)Cl)c(C)c1.NCCCCN>>Cc1cc(C)c(S(=O)(=O)NCCCCNS(=O)(=O)c2c(C)cc(C)cc2C)c(C)c1 | C1(=C(C(=CC(=C1)C)C)S(=O)(=O)Cl)C.NCCCCN>>C1(=C(C(=CC(=C1)C)C)S(=O)(=O)NCCCCNS(=O)(=O)C1=C(C=C(C=C1C)C)C)C | Cl[S:7]([c:6]1[c:23]([CH3:24])[cH:22][c:2]([CH3:1])[cH:30][c:28]1[CH3:29])(=[O:8])=[O:9].[CH2:3]([CH2:4][CH2:5][NH2:10])[CH2:14][NH2:15]>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([S:7](=[O:8])(=[O:9])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][S:16](=[O:17])(=[O:18])[c:19]2[c:20]([CH3:21])[cH:22][c:23]([CH3:24])[cH:25... | Cc1cc(C)c(S(=O)(=O)Cl)c(C)c1.NCCCCN | Cc1cc(C)c(S(=O)(=O)NCCCCNS(=O)(=O)c2c(C)cc(C)cc2C)c(C)c1 | null | null | [OH-].[Na+].C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | e4d9d7fc6666959977fbf8132e7d8913fe3ccae568038c3a25f79e909aff7c7c | 49e17eef2449ba97ee4819a6ce246acf1c58e3d5b3abe8a2f31d396efdacf84d | O=S(=O)(NCCCCNS(=O)(=O)c1ccccc1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[c:5](-[C;D1;H3:6]):[c:7]:[c;H0;D3;+0:8](-[C;D1;H3:9]):[cH;D2;+0:10]:[c;H0;D3;+0:11]:1-[C;D1;H3:12].[NH2;D1;+0:13]-[CH2;D2;+0:14]-[CH2;D2;+0:15]-[CH2;D2;+0:16]-[CH2;D2;+0:17]-[NH2;D1;+0:18]>>[C;D1;H3:9]-[c;H0;D3;+0:8]1:[c:7]:[c:5](-[C;D1;H3:6]):[c;H0;D3;+0:4... | 90 | [{"value": 90.0, "product": "C1(=C(C(=CC(=C1)C)C)S(=O)(=O)NCCCCNS(=O)(=O)C1=C(C=C(C=C1C)C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.5, "product": "C1(=C(C(=CC(=C1)C)C)S(=O)(=O)NCCCCNS(=O)(=O)C1=C(C=C(C=C1C)C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | 2-Mesitylenesulfonyl chloride (54.40 g, 0.249 mol) in CH2Cl2 (300 ml) was added to 1,4-diaminobutane (11.34 g, 0.129 mol) in 1 N NaOH (300 ml) at 0° C., and the biphasic mixture was stirred for 24 hours at room temperature. Organic solvent was evaporated and 2.4 N HCl (250 ml) was added to the combined portions. Solid ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Primary amine.Sulfonyl halide | Sulfonamide.Sulfonamide | c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | null | [OH-].[Na+].C(Cl)Cl | null | 24 | Cc1cc(C)c(S(=O)(=O)Cl)c(C)c1.NCCCCN>[OH-].[Na+].C(Cl)Cl>Cc1cc(C)c(S(=O)(=O)NCCCCNS(=O)(=O)c2c(C)cc(C)cc2C)c(C)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dc1fa503d8b442db9694da96e0879be1 | Cc1cc(C)c(S(=O)(=O)Cl)c(C)c1.OCCC1CCNCC1>>Cc1cc(C)c(S(=O)(=O)OCCC2CCN(S(=O)(=O)c3c(C)cc(C)cc3C)CC2)c(C)c1 | C1(=C(C(=CC(=C1)C)C)S(=O)(=O)Cl)C.N1CCC(CC1)CCO>>CC1=C(C(=CC(=C1)C)C)S(=O)(=O)N1CCC(CC1)CCOS(=O)(=O)C1=C(C=C(C=C1C)C)C | Cl[S:7]([c:6]1[c:24]([CH3:25])[cH:3][c:2]([CH3:1])[cH:32][c:31]1[CH3:5])(=[O:8])=[O:9].[OH:10][CH2:11][CH2:12][CH:13]1[CH2:14][CH2:15][NH:16][CH2:29][CH2:30]1>>[CH3:1][c:2]1[cH:3][c:4]([CH3:5])[c:6]([S:7](=[O:8])(=[O:9])[O:10][CH2:11][CH2:12][CH:13]2[CH2:14][CH2:15][N:16]([S:17](=[O:18])(=[O:19])[c:20]3[c:21]([CH3:22])... | Cc1cc(C)c(S(=O)(=O)Cl)c(C)c1.OCCC1CCNCC1 | Cc1cc(C)c(S(=O)(=O)OCCC2CCN(S(=O)(=O)c3c(C)cc(C)cc3C)CC2)c(C)c1 | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | 3a84d1d118995a3875138345738afc2f77691666e3414ebbb2805c8c9ab26406 | 336c2018f2656bb6f8a9f916ae1945c5b6aece99517a0b2dd11edeef58f4c413 | O=S(=O)(OCCC1CCN(S(=O)(=O)c2ccccc2)CC1)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c;H0;D3;+0:4]1:[c;H0;D3;+0:5](-[C;D1;H3:6]):[cH;D2;+0:7]:[c;H0;D3;+0:8](-[C;D1;H3:9]):[cH;D2;+0:10]:[c;H0;D3;+0:11]:1-[CH3;D1;+0:12].[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17].[C:18]-[C:19]-[OH;D1;+0:20]>>[C:13]-[C:14]-[N;H0;D3;+0:15](-[#16:21](=[O;D1;H0:22])(=[O;D1;H0:23])... | null | [] | null | null | 44 | HOUR | 2-Mesitylenesulfonyl chloride (24.78 g, 0.113 mol) in pyridine (60 ml) was added all at once to 4-piperidine-ethanol (5.58 g, 43.2 mmol) in pyridine (25 ml) at −16° C.; the temperature rose to −11° C. The flask was stored in the refrigerator at 5.5° C. for 44 hours under argon. The reaction mixture was poured into ice ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine.Sulfonyl halide | Tertiary amine.Sulfonate | c1ccccc1.C1CCNCC1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | c1ccccc1.C1CC[NH]CC1.c1ccccc1 | null | N1=CC=CC=C1 | null | 44 | Cc1cc(C)c(S(=O)(=O)Cl)c(C)c1.OCCC1CCNCC1>N1=CC=CC=C1>Cc1cc(C)c(S(=O)(=O)OCCC2CCN(S(=O)(=O)c3c(C)cc(C)cc3C)CC2)c(C)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1bb450c743ff480295cb2836392ef9e4 | C1=COCCC1.Oc1ccc(I)cc1>>Ic1ccc(OC2CCCCO2)cc1 | C=1(C(=CC=CC1)S(=O)(=O)O)C.IC1=CC=C(C=C1)O.O1CCCC=C1>>IC1=CC=C(C=C1)OC1OCCCC1 | [CH:7]1=[CH:8][CH2:9][CH2:10][CH2:11][O:12]1.[I:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:13][cH:14]1>>[I:1][c:2]1[cH:3][cH:4][c:5]([O:6][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][O:12]2)[cH:13][cH:14]1 | C1=COCCC1.Oc1ccc(I)cc1 | Ic1ccc(OC2CCCCO2)cc1 | null | CC=1C=CC(=CC1)S(=O)(=O)O | C(Cl)Cl | Heteroatom Alkylation and Arylation | oxa-Michael addition | 1c7c788bec8addec628516b12629525fab255984248a4af23c71106a7726e25d | da6d2e768f263ce18da31b53a21ee41abe25d00717257e942f83f912a04f86d8 | c1ccc(OC2CCCCO2)cc1 | [#8:1]1-[C:2]-[C:3]-[C:4]-[CH;D2;+0:5]=[CH;D2;+0:6]-1.[OH;D1;+0:7]-[c:8](:[c:9]):[c:10]>>[c:9]:[c:8](-[O;H0;D2;+0:7]-[CH;D3;+0:6]1-[#8:1]-[C:2]-[C:3]-[C:4]-[CH2;D2;+0:5]-1):[c:10] | 92.1 | [{"value": 92.0, "product": "IC1=CC=C(C=C1)OC1OCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.1, "product": "IC1=CC=C(C=C1)OC1OCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 20 | CELSIUS | 15 | MINUTE | To a stirred solution of 4-iodophenol (11.0 g, 50 mmol) in CH2Cl2 (50 ml) cooled with an ice bath, dihydropyran (5.0 g, 60 mmol) was added dropwise over 10 min at 0–5° C. After the solution became clear, toluenesulfonic acid, TsOH, (10 mg) was added. The solution was stirred at 20° C. for 15 min. Then it was quenched b... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Aromatic alcohol | Ether.Ether | C1=COCCC1 | C1CCOCC1 | c1ccccc1.C1CCOCC1 | null | CC=1C=CC(=CC1)S(=O)(=O)O.C(Cl)Cl | 20 | 0.25 | C1=COCCC1.Oc1ccc(I)cc1>CC=1C=CC(=CC1)S(=O)(=O)O.C(Cl)Cl>Ic1ccc(OC2CCCCO2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-eeefb2a199d048a9aeec94c9f646f6f9 | C#C[Si](C)(C)C.Ic1ccc(OC2CCCCO2)cc1>>C[Si](C)(C)C#Cc1ccc(OC2CCCCO2)cc1 | C[Si](C)(C)C#C.IC1=CC=C(C=C1)OC1OCCCC1>>O1C(CCCC1)OC1=CC=C(C=C1)C#C[Si](C)(C)C | [CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[CH:6].I[c:7]1[cH:8][cH:9][c:10]([O:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][O:17]2)[cH:18][cH:19]1>>[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][O:17]2)[cH:18][cH:19]1 | C#C[Si](C)(C)C.Ic1ccc(OC2CCCCO2)cc1 | C[Si](C)(C)C#Cc1ccc(OC2CCCCO2)cc1 | 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.[Cu]I | C(C)(C)NC(C)C | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | c1ccc(OC2CCCCO2)cc1 | I-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C;D1;H3:6]-[#14:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:10]#[CH;D1;+0:11]>>[C;D1;H3:6]-[#14:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:10]#[C;H0;D2;+0:11]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 2 | HOUR | To a degassed solution of compound 1 (9.12 g, 30 mmol) in diisopropylamine (180 ml) under nitrogen, Pd(PPh3)2Cl2 (140 mg, 0.2 mmol) and CuI (78 mg, 0.4 mmol) were added. Then trimethylsilyl acetylene (3.3 g, 33 mmol) was added dropwise to this clear solution. The reaction mixture was stirred for 2 hours at room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCOCC1 | HI | 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.[Cu]I.C(C)(C)NC(C)C | null | 2 | C#C[Si](C)(C)C.Ic1ccc(OC2CCCCO2)cc1>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.[Cu]I.C(C)(C)NC(C)C>C[Si](C)(C)C#Cc1ccc(OC2CCCCO2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9f5b87a7370b42dc9bc44c6cfc944008 | C[Si](C)(C)C#Cc1ccc(OC2CCCCO2)cc1>>C#Cc1ccc(OC2CCCCO2)cc1 | O1C(CCCC1)OC1=CC=C(C=C1)C#C[Si](C)(C)C>>O1C(CCCC1)OC1=CC=C(C=C1)C#C | C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][O:13]2)[cH:14][cH:15]1>>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([O:7][CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][O:13]2)[cH:14][cH:15]1 | C[Si](C)(C)C#Cc1ccc(OC2CCCCO2)cc1 | C#Cc1ccc(OC2CCCCO2)cc1 | null | null | CO | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | c1ccc(OC2CCCCO2)cc1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3]>>[CH;D1;+0:1]#[C:2]-[c:3] | null | [] | null | null | 4 | HOUR | (9.3 g, 160 mmol) was added to a stirred solution of 2 (22.6 g, 80 mmol) in MeOH (150 ml). The reaction mixture was stirred at room temperature for about 4 hours. After the reaction finished (GC shows no starting material remaining), the solvent was removed under reduced pressure on a rotary evaporator. The residue was... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1ccccc1.C1CCOCC1 | Other | CO | null | 4 | C[Si](C)(C)C#Cc1ccc(OC2CCCCO2)cc1>CO>C#Cc1ccc(OC2CCCCO2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d3dd416e317947b78c70bab9354dfb39 | C#Cc1ccc(OC2CCCCO2)cc1.FC(F)(F)c1ccc(Br)cc1>>FC(F)(F)c1ccc(C#Cc2ccc(OC3CCCCO3)cc2)cc1 | O1C(CCCC1)OC1=CC=C(C=C1)C#C.BrC1=CC=C(C=C1)C(F)(F)F>>O1C(CCCC1)OC1=CC=C(C=C1)C#CC1=CC=C(C=C1)C(F)(F)F | [CH:9]#[C:10][c:11]1[cH:12][cH:13][c:14]([O:15][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][O:21]2)[cH:22][cH:23]1.Br[c:8]1[cH:7][cH:6][c:5]([C:2]([F:1])([F:3])[F:4])[cH:25][cH:24]1>>[F:1][C:2]([F:3])([F:4])[c:5]1[cH:6][cH:7][c:8]([C:9]#[C:10][c:11]2[cH:12][cH:13][c:14]([O:15][CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20][O:21]3... | C#Cc1ccc(OC2CCCCO2)cc1.FC(F)(F)c1ccc(Br)cc1 | FC(F)(F)c1ccc(C#Cc2ccc(OC3CCCCO3)cc2)cc1 | 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.[Cu]I | C(C)(C)NC(C)C | C-C Coupling | Sonogashira alkyne_aryl halide | 15c08902746c61a960c314898ce6bb5fcc5e189f9e057388c59dba9ec9d0c81c | 305eca0fd2975da49e7f69e4edfb9dc1cbce82513954bc5a73be3289e70e5f76 | C(#Cc1ccc(OC2CCCCO2)cc1)c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[CH;D1;+0:6]#[C:7]-[c:8]>>[c:8]-[C:7]#[C;H0;D2;+0:6]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | 80 | CELSIUS | 2 | HOUR | A solution of 3 (12.1 g, 60 mmol) and 4-bromobenzotriflouride (14.85 g, 66 mmol) in diisopropylamine (250 ml) was heated to 30° C. under nitrogen, and the solution was degassed. Then Pd(PPh3)2Cl2 (210 mg, 0.3 mmol) and copper(I) iodide (114 mg, 0.6 mmol) were added to this clear solution. The reaction mixture was stirr... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Alkyne | Alkyne | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.C1CCOCC1 | HBr | 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.[Cu]I.C(C)(C)NC(C)C | 80 | 2 | C#Cc1ccc(OC2CCCCO2)cc1.FC(F)(F)c1ccc(Br)cc1>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.[Cu]I.C(C)(C)NC(C)C>FC(F)(F)c1ccc(C#Cc2ccc(OC3CCCCO3)cc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-001c79b908c44af0b3cbb88ecfd5d8af | FC(F)(F)c1ccc(C#Cc2ccc(OC3CCCCO3)cc2)cc1>>Oc1cccc(C#Cc2ccc(C(F)(F)F)cc2)c1 | O1C(CCCC1)OC1=CC=C(C=C1)C#CC1=CC=C(C=C1)C(F)(F)F.C(Cl)Cl.CC=1C=CC(=CC1)S(=O)(=O)O>>OC=1C=CC=C(C1)C#CC1=CC=C(C=C1)C(F)(F)F | C1CCC([O:1][c:2]2[cH:3][cH:19][c:6]([C:7]#[C:8][c:9]3[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]3)[cH:5][cH:4]2)OC1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([C:7]#[C:8][c:9]2[cH:10][cH:11][c:12]([C:13]([F:14])([F:15])[F:16])[cH:17][cH:18]2)[cH:19]1 | FC(F)(F)c1ccc(C#Cc2ccc(OC3CCCCO3)cc2)cc1 | Oc1cccc(C#Cc2ccc(C(F)(F)F)cc2)c1 | null | null | CO | Miscellaneous | OtherReaction | 16dbd123c57e1815d831a6d1b3507538729761040e5fd17321613b472b962401 | 97b700253a515732e056bebfec7d29d55492867916f45a12199b66c78e6a3460 | C(#Cc1ccccc1)c1ccccc1 | [c:1]-[C:2]#[C:3]-[c:4]1:[c:5]:[cH;D2;+0:6]:[c;H0;D3;+0:7](-[O;H0;D2;+0:8]-C2-C-C-C-C-O-2):[cH;D2;+0:9]:[cH;D2;+0:10]:1>>[OH;D1;+0:8]-[c;H0;D3;+0:7]1:[cH;D2;+0:10]:[c:4](-[C:3]#[C:2]-[c:1]):[c:5]:[cH;D2;+0:6]:[cH;D2;+0:9]:1 | 9,057.1 | [{"value": 90.0, "product": "OC=1C=CC=C(C1)C#CC1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 9057.1, "product": "OC=1C=CC=C(C1)C#CC1=CC=C(C=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 30 | CELSIUS | 1 | HOUR | Coumpound 4 (13.84 g, 40 mmol), CH2Cl2 (75 ml) and MeOH (125 ml) were placed in a 250 ml round bottomed flask, then TsOH (0.4 g, 0.4 mmol) was added. The reaction mixture was stirred at 30° C. for 1 hour. When the reaction was finished (TLC shows no starting material remaining), the solvent was removed by rotary evapor... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol | C1CCOCC1.c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | CO | 30 | 1 | FC(F)(F)c1ccc(C#Cc2ccc(OC3CCCCO3)cc2)cc1>CO>Oc1cccc(C#Cc2ccc(C(F)(F)F)cc2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd33ac29f3d04c6eaaab7d588e3dff45 | CCCCOC(=O)c1ccc(N)cc1.N#C[S-].O=C(Cl)c1ccc2ccccc2c1>>CCCCOC(=O)c1ccc(NC(=S)NC(=O)c2ccc3ccccc3c2)cc1 | C1=C(C=CC2=CC=CC=C12)C(=O)Cl.[S-]C#N.[NH4+].NC1=CC=C(C(=O)OCCCC)C=C1>>C(CCC)OC(C1=CC=C(C=C1)NC(=S)NC(=O)C1=CC2=CC=CC=C2C=C1)=O | [CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([NH2:12])[cH:28][cH:29]1.[C:13]([S-:14])#[N:15].Cl[C:16](=[O:17])[c:18]1[cH:19][cH:20][c:21]2[cH:22][cH:23][cH:24][cH:25][c:26]2[cH:27]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[S:14])[NH:15][C:16](=[... | CCCCOC(=O)c1ccc(N)cc1.N#C[S-].O=C(Cl)c1ccc2ccccc2c1 | CCCCOC(=O)c1ccc(NC(=S)NC(=O)c2ccc3ccccc3c2)cc1 | null | null | CC(=O)C | Acylation | OtherReaction | ba32abf48e55d53ef6e0af57f1d7169ed0ac841ff7858c991011fd961a061dc2 | b88d5f877c80e8bb46ad5808630e5b77d7f3aea35cbafadf6b92b5b8202ff7a7 | O=C(NC(=S)Nc1ccccc1)c1ccc2ccccc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[N;H0;D1;+0:6]#[C;H0;D2;+0:7]-[S-;H0;D1:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1](-[NH;D2;+0:6]-[C;H0;D3;+0:7](=[S;H0;D1;+0:8])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 1 | HOUR | 2-Naphthoyl chloride (190 mg, 1 mmol) is added to a solution of ammonium thiocyanate (200 mg, about 3 mmol) in acetone (5 ml) and stirred at room temperature for 1 hour. Butyl 4-aminobenzoate (180 mg, 0.93 mmol) is added to the reaction mixture. Stirring is continued overnight at room temperature. The solid, which form... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Nitrile.Primary amine | Thiourea.Secondary amide | null | null | c1ccccc1.c1ccc2ccccc2c1 | Other | CC(=O)C | null | 1 | CCCCOC(=O)c1ccc(N)cc1.N#C[S-].O=C(Cl)c1ccc2ccccc2c1>CC(=O)C>CCCCOC(=O)c1ccc(NC(=S)NC(=O)c2ccc3ccccc3c2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3b497646d789449c819e60ce8634b53c | CCCCOC(=O)c1ccc(N=C=S)cc1.CNC(=O)COc1ccccc1>>CCCCOC(=O)c1ccc(NC(=S)N(C)C(=O)COc2ccccc2)cc1 | CC(C)(C)[O-].[K+].O(C1=CC=CC=C1)CC(=O)NC.C(CCC)OC(C1=CC=C(C=C1)N=C=S)=O>>C(CCC)OC(C1=CC=C(C=C1)NC(=S)N(C(COC1=CC=CC=C1)=O)C)=O | [CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([N:12]=[C:13]=[S:14])[cH:27][cH:28]1.[NH:15]([CH3:16])[C:17](=[O:18])[CH2:19][O:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([NH:12][C:13](=[S:14])[N:15]([CH3:16])[C:17](=[O... | CCCCOC(=O)c1ccc(N=C=S)cc1.CNC(=O)COc1ccccc1 | CCCCOC(=O)c1ccc(NC(=S)N(C)C(=O)COc2ccccc2)cc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 5c3f709ce78dad45613b201efabf0dcb5ede491d0721b6f902048ff9fa018c70 | 43eda399ba8c48d07548472f2e4ea209c9863e42a9d42fa29ffa8a810d7a89a6 | O=C(COc1ccccc1)NC(=S)Nc1ccccc1 | [C:1]-[C:2](=[O;D1;H0:3])-[NH;D2;+0:4]-[C;D1;H3:5].[S;D1;H0:6]=[C;H0;D2;+0:7]=[N;H0;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[C:1]-[C:2](=[O;D1;H0:3])-[N;H0;D3;+0:4](-[C;D1;H3:5])-[C;H0;D3;+0:7](=[S;D1;H0:6])-[NH;D2;+0:8]-[c:9](:[c:10]):[c:11] | 10 | [{"value": 10.0, "product": "C(CCC)OC(C1=CC=C(C=C1)NC(=S)N(C(COC1=CC=CC=C1)=O)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | t-BuOK (0.55 mL of 1.0 N solution) in THF is added to a solution of phenoxy-N-methylacetamide (83 mg, 0.5 mmol) in THF (5 mL). After 5 minutes, butyl-4-isothiocyanatobenzoate (118 mg, 0.5 mmol) is added in one portion and the resultant mixture is stirred overnight. The crude mixture is filtered through a silica pad. Af... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Isothiocyanate | Thiourea | null | null | c1ccccc1.c1ccccc1 | null | C1CCOC1 | null | 0.083333 | CCCCOC(=O)c1ccc(N=C=S)cc1.CNC(=O)COc1ccccc1>C1CCOC1>CCCCOC(=O)c1ccc(NC(=S)N(C)C(=O)COc2ccccc2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-32423f84d6c1444db24b353eaff2d0d9 | C=Cc1ccccc1>>C=Cc1ccccc1 | C=CC1=CC=CC=C1.C(C=C)#N.P(=O)([O-])([O-])[O-].[Ca+2].[Ca+2].[Ca+2].P(=O)([O-])([O-])[O-].CC(C)(C#N)N=NC(C)(C)C#N>>C=CC#N.C=CC1=CC=CC=C1 | [CH2:5]=[CH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH2:5]=[CH:6][c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1 | C=Cc1ccccc1 | C=Cc1ccccc1 | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccccc1 | null | null | [] | null | null | 180 | MINUTE | 71 parts of styrene, 29 parts of acrylonitrile, 120 parts of deionized water and 0.2 parts of azobisisobutylonitrile (AIBN) were blended. To the blend, 0.5 parts of tricalciumphosphate and 0.3 parts of mercaptan-containing chain transfer agent were added. The resultant solution was heated to 80° C. for 90 minutes and k... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1 | null | O | null | 3 | C=Cc1ccccc1>O>C=Cc1ccccc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2f21ab4ae6b24aae8d92c7c7db426ccc | O=C([O-])C1C2C=CC(C2)C1C(=O)[O-].[Na+]>>O=C([O-])C1C2CCC(C2)C1C(=O)[O-].[Na+] | C12C(C(C(C=C1)C2)C(=O)[O-])C(=O)[O-].[Na+].[Na+]>>C12C(C(C(CC1)C2)C(=O)[O-])C(=O)[O-].[Na+].[Na+] | [O:1]=[C:2]([O-:3])[CH:4]1[CH:5]2[CH:6]=[CH:7][CH:8]([CH2:9]2)[CH:10]1[C:11](=[O:12])[O-:13].[Na+:15]>>[O:1]=[C:2]([O-:3])[CH:4]1[CH:5]2[CH2:6][CH2:7][CH:8]([CH2:9]2)[CH:10]1[C:11](=[O:12])[O-:13].[Na+:15] | O=C([O-])C1C2C=CC(C2)C1C(=O)[O-].[Na+] | O=C([O-])C1C2CCC(C2)C1C(=O)[O-].[Na+] | null | [Pd] | O | Miscellaneous | OtherReaction | 3f43743134a5de32528d95c060c25e5a7d7de42b355c50547d48d8cb02da2515 | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | C1CC2CCC1C2 | [O;-;D1;H0:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[C:5](-[C:6](-[O;-;D1;H0:7])=[O;D1;H0:8])-[C:9]2-[C:10]-[C:11]-1-[CH;D2;+0:12]=[CH;D2;+0:13]-2>>[O;-;D1;H0:1]-[C:2](=[O;D1;H0:3])-[C:4]1-[C:5](-[C:6](-[O;-;D1;H0:7])=[O;D1;H0:8])-[C:9]2-[C:10]-[C:11]-1-[CH2;D2;+0:12]-[CH2;D2;+0:13]-2 | null | [] | null | null | 8 | HOUR | To a solution of disodium bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (10.0 g, from example 3) in water (100 g) was added 0.5 g palladium on activated carbon (5 wt %). The mixture was transferred into a Parr reactor and was subjected to hydrogenation (50 psi, room temperature) for 8 hours. The activated carbon was filte... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CC2CCC1C2 | C1CC2CCC1C2 | C1CC2CCC1C2 | null | [Pd].O | null | 8 | O=C([O-])C1C2C=CC(C2)C1C(=O)[O-].[Na+]>[Pd].O>O=C([O-])C1C2CCC(C2)C1C(=O)[O-].[Na+] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c0156d75e2c14a898911d22916c87e2d | [Ca+2]>>[Ca+2] | C12C(C(C(CC1)C2)C(=O)[O-])C(=O)[O-].[Na+].[Na+].O.O.[Cl-].[Ca+2].[Cl-]>>C12C(C(C(CC1)C2)C(=O)[O-])C(=O)[O-].[Ca+2] | [Ca+2:14]>>[Ca+2:14] | [Ca+2] | [Ca+2] | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | 60 | CELSIUS | 2 | HOUR | To a solution of disodium bicyclo[2.2.1]heptane-2,3-dicarboxylate (22.6 g, 0.1 mol) in water (150 g) was added a solution of calcium chloride dihydrate (14.7 g, 0.1 mol) in water (100 g). The mixture stirred at 60° C. for 2 hours. The resulting white precipitate was filtered. The white powdery product was dried and mil... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | 60 | 2 | [Ca+2]>O>[Ca+2] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9012a462bfb94024b4c6414b67674db0 | C=CC(=O)OCCCC>>C=CC(=O)OCCCC | S(=O)(=O)(OCCCCCCCCCCCC)[O-].[Na+].C(C=C)#N.C(C=C)(=O)OCCCC>>C(C=C)#N.C(C=C)(=O)OCCCC | [CH2:5]=[CH:6][C:7](=[O:8])[O:9][CH2:10][CH2:11][CH2:12][CH3:13]>>[CH2:5]=[CH:6][C:7](=[O:8])[O:9][CH2:10][CH2:11][CH2:12][CH3:13] | C=CC(=O)OCCCC | C=CC(=O)OCCCC | null | null | O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | null | [] | 80 | CELSIUS | 10 | HOUR | Into a 2 L reactor equipped with an agitator, a thermometer, a nitrogen gas inlet tube, a dropping funnel, and a reflux condenser, was placed 600 g of distilled water, 0.71 g of sodium dodecyl sulfate as an emulsifier, and as monomers, 70 g of acrylonitrile and 30 g of n-butyl acrylate, and the reactor was nitrogen-pur... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | O | 80 | 10 | C=CC(=O)OCCCC>O>C=CC(=O)OCCCC |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a4ae9e8f6ba440f926878548739f414 | C1CCCCC1.O=C(O)C1=CCCCC1>>O=C1C2=C(CCCC2)C2CCCCC12 | C1(=CCCCC1)C(=O)O.C1CCCCC1.S(=O)(=O)([O-])[O-].[NH4+].[NH4+]>>C1CCCC2C=3CCCCC3C(C12)=O | [CH2:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1.O[C:2](=[O:1])[C:14]1=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13]1>>[O:1]=[C:2]1[C:3]2=[C:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]12 | C1CCCCC1.O=C(O)C1=CCCCC1 | O=C1C2=C(CCCC2)C2CCCCC12 | null | null | O | C-C Coupling | OtherReaction | 30b2100907c086f57836aa17450222e20e67139f5d22b81ca8cbd745fbb8324f | a49756d2995b35bf1c4b6840928f031562470ef5bd676447fb43ce2575147daa | O=C1C2=C(CCCC2)C2CCCCC12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3]1=[CH;D2;+0:4]-[C:5]-[C:6]-[C:7]-[C:8]-1.[C:9]1-[C:10]-[C:11]-[C:12]-[CH2;D2;+0:13]-[CH2;D2;+0:14]-1>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C;H0;D3;+0:13]2=[C;H0;D3;+0:14](-[C:9]-[C:10]-[C:11]-[C:12]-2)-[CH;D3;+0:4]2-[C:5]-[C:6]-[C:7]-[C:8]-[CH;D3;+0:3]-1-2 | 43 | [{"value": 43.0, "product": "C1CCCC2C=3CCCCC3C(C12)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 4.5 | HOUR | In a 250 ml three neck round bottom flask, equipped with a mechanical stirrer, a thermometer and a reflux condenser 16.276 g of polyphosphoric acid was charged and heated to a temperature of 70° C. 16.276 g of 1-cyclohexenecarboxylic acid and 10.592 g of cyclohexane were added dropwise maintaining a temperature of the ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | C1CCCCC1.C1=CCCCC1 | C1CCC2=C(C1)CC1CCCCC21 | C1CCC2=C(C1)CC1CCCCC21 | HO- | O | 70 | 4.5 | C1CCCCC1.O=C(O)C1=CCCCC1>O>O=C1C2=C(CCCC2)C2CCCCC12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-079cc66065be4b169c9108c6a8bd6faf | O=C1C2=C(CCCC2)C2CCCCC12>>CC1=C2CCCCC2C2=C1CCCC2 | Cl.C1CCCC2C=3CCCCC3C(C12)=O.C[Mg]Br>>CC=1C=2CCCCC2C2CCCCC12 | O=[C:8]1[CH:3]2[CH:2]([CH2:7][CH2:6][CH2:5][CH2:4]2)[C:10]2=[C:9]1[CH2:14][CH2:13][CH2:12][CH2:11]2>>[CH3:1][C:2]1=[C:3]2[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]2[C:9]2=[C:10]1[CH2:11][CH2:12][CH2:13][CH2:14]2 | O=C1C2=C(CCCC2)C2CCCCC12 | CC1=C2CCCCC2C2=C1CCCC2 | null | null | O1CCCC1 | Miscellaneous | OtherReaction | 31a9ddf1be707eee87db5e81934c32eb6582706e14f7a8f4c3c9ec6e09b8e3ba | 9db0f73aed071f5fa7238b261fc87a241efa69e871d2f239452605149d0c954e | C1=C2CCCCC2C2=C1CCCC2 | O=[C;H0;D3;+0:1]1-[C:2](=[C:3](-[C:4])-[CH;D3;+0:5]2-[CH2;D2;+0:6]-[C:7]-[C:8]-[C:9]-[CH;D3;+0:10]-1-2)-[C:11]>>[C:4]-[C:3]1=[C:2](-[C:11])-[CH;D3;+0:1]2-[CH2;D2;+0:6]-[C:7]-[C:8]-[C:9]-[C;H0;D3;+0:10]-2=[C;H0;D3;+0:5]-1-[C;D1;H3:12] | 92 | [{"value": 92.0, "product": "CC=1C=2CCCCC2C2CCCCC12", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.8, "product": "CC=1C=2CCCCC2C2CCCCC12", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a solution of 1,2,3,4,4a,5,6,7,8,9a-decahydrofluoren-9-one (90.7 mg, 0.477 mmol) in tetrahydrofuran (5 ml), 0.35 ml (1.05 mmol) of methylmagnesium bromide (3.0 M in Et2O) was added dropwise under nitrogen at −78° C. The resulting cloudy mixture was kept at −78° C. for 3 hours and then allowed to warm to room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1CCC2=C(C1)CC1CCCCC21 | C1=C2CCCCC2C2=C1CCCC2 | C1=C2CCCCC2C2=C1CCCC2 | null | O1CCCC1 | null | 3 | O=C1C2=C(CCCC2)C2CCCCC12>O1CCCC1>CC1=C2CCCCC2C2=C1CCCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2089ca02cdbb49f195f3df439abb0e82 | C1=CCCC1.O=C(O)C1=CCCC1>>O=C1C2=C(CCC2)[C@H]2CCC[C@@H]12 | C1(=CCCC1)C(=O)O.C1=CCCC1>>C1=2C([C@@H]3CCC[C@@H]3C2CCC1)=O | [CH:8]1=[CH:12][CH2:11][CH2:10][CH2:9]1.O=[C:2]([OH:1])[C:3]1=[CH:4][CH2:5][CH2:6][CH2:7]1>>[O:1]=[C:2]1[C:3]2=[C:4]([CH2:5][CH2:6][CH2:7]2)[C@H:8]2[CH2:9][CH2:10][CH2:11][C@@H:12]12 | C1=CCCC1.O=C(O)C1=CCCC1 | O=C1C2=C(CCC2)[C@H]2CCC[C@@H]12 | null | null | S(=O)(=O)([O-])[O-].[NH4+].[NH4+] | Acylation | OtherReaction | 2fce04924b3f49945a37977f6822da19258f5fda09c938ebedc90ef567e3eb62 | 26fa8fd71cdd2db70d55c60f92a5587664090781bde28495d3bab102e1ae668a | O=C1C2=C(CCC2)[C@H]2CCC[C@@H]12 | O=[C;H0;D3;+0:1](-[OH;D1;+0:2])-[C:3]1=[CH;D2;+0:4]-[C:5]-[C:6]-[C:7]-1.[C:8]1-[C:9]-[CH;D2;+0:10]=[CH;D2;+0:11]-[C:12]-1>>[O;H0;D1;+0:2]=[C;H0;D3;+0:1]1-[C:3]2=[C;H0;D3;+0:4](-[C:5]-[C:6]-[C:7]-2)-[C@H;D3;+0:11]2-[C:12]-[C:8]-[C:9]-[C@@H;D3;+0:10]-1-2 | null | [] | 30 | CELSIUS | 4 | HOUR | A stirred suspension of 1-cyclopentene carboxylic acid (11.2 g, 100 mmol) and cyclopentene (13.6 g, 200 mmol) was added slowly to stirring polyphosphoric acid (Aldrich, 300 g) at 60° C. in a 250 mL flask. The reaction mixture was stirred at 70–80° C. for 4 hours under nitrogen. The dark brown reaction mixture was coole... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | C1=CCCC1.C1=CCCC1 | C1CC2=C(C1)[C@H]1CCC[C@H]1C2 | C1CC2=C(C1)[C@H]1CCC[C@H]1C2 | HO- | S(=O)(=O)([O-])[O-].[NH4+].[NH4+] | 30 | 4 | C1=CCCC1.O=C(O)C1=CCCC1>S(=O)(=O)([O-])[O-].[NH4+].[NH4+]>O=C1C2=C(CCC2)[C@H]2CCC[C@@H]12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e7e86c6093174ea1bac2f28462d3f752 | CC(C)(C)OC(=O)NCCCN.O=S(=O)(Cl)c1cccc2cnccc12>>CC(C)(C)OC(=O)NCCCNS(=O)(=O)c1cccc2cnccc12 | C(C)(C)(C)OC(=O)NCCCN.C(C)N(CC)CC.C1=NC=CC=2C(=CC=CC12)S(=O)(=O)Cl>>C(C)(C)(C)OC(=O)NCCCNS(=O)(=O)C1=C2C=CN=CC2=CC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][NH2:12].Cl[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][c:20]2[cH:21][n:22][cH:23][cH:24][c:25]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][NH:12][S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19]... | CC(C)(C)OC(=O)NCCCN.O=S(=O)(Cl)c1cccc2cnccc12 | CC(C)(C)OC(=O)NCCCNS(=O)(=O)c1cccc2cnccc12 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccc2cnccc2c1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 30 | MINUTE | A solution of N-(tert-butoxycarbonyl)-1,3-propylenediamine (2.09 g, Tokyo Kasei Kogyo) and triethylamine (3.4 ml, Tokyo Kasei Kogyo) in dichloromethane (20 ml) was added with a solution of isoquinoline-5-sulfonyl chloride (2.73 g, prepared according to Japanese Patent Unexamined Publication (Kokai) No. 61-227581) in di... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2cnccc2c1 | HCl | ClCCl | null | 0.5 | CC(C)(C)OC(=O)NCCCN.O=S(=O)(Cl)c1cccc2cnccc12>ClCCl>CC(C)(C)OC(=O)NCCCNS(=O)(=O)c1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-99be45a0fb164c68b4577c67d8e9e37e | CC(C)(C)OC(=O)NCCCNS(=O)(=O)c1cccc2cnccc12.CCCCP(CCCC)CCCC.CN(C)C(=O)N=NC(=O)N(C)C>>CC(C)(C)OC(=O)NCCCN(CCCc1ccccc1)S(=O)(=O)c1cccc2cnccc12 | C(C)(C)(C)OC(=O)NCCCNS(=O)(=O)C1=C2C=CN=CC2=CC=C1.N(=NC(=O)N(C)C)C(=O)N(C)C.C1(=CC=CC=C1)CCCO.C(CCC)P(CCCC)CCCC>>C(C)(C)(C)OC(=O)NCCCN(CCCC1=CC=CC=C1)S(=O)(=O)C1=C2C=CN=CC2=CC=C1.C1(=CC=CC=C1)CCCO | [CH3:1][C:2]([CH3:4])([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][NH:12][S:22](=[O:23])(=[O:24])[c:25]1[cH:26][cH:27][cH:28][c:29]2[cH:30][n:31][cH:32][cH:33][c:34]12)[CH3:17].CC[CH2:14][CH2:15]P(CCC[CH3:18])[CH2:19][CH2:20][CH2:21][CH3:16].CN(C)C(=O)N=NC(=O)N([CH3:3])[CH3:13]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C... | CC(C)(C)OC(=O)NCCCNS(=O)(=O)c1cccc2cnccc12.CCCCP(CCCC)CCCC.CN(C)C(=O)N=NC(=O)N(C)C | CC(C)(C)OC(=O)NCCCN(CCCc1ccccc1)S(=O)(=O)c1cccc2cnccc12 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | 8337f786eb5fde5cab8e70a191935fd4582a55c6eff8a0b3bf08e5877685842e | 51b0ac63f70b1c36d791c24a3cb1506a541098df476fbc0f63b74e39d5ee1859 | O=S(=O)(NCCCc1ccccc1)c1cccc2cnccc12 | C-C-[CH2;D2;+0:1]-[CH2;D2;+0:2]-P(-C-C-C-[CH3;D1;+0:3])-[CH2;D2;+0:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[CH3;D1;+0:7].C-N(-C)-C(=O)-N=N-C(=O)-N(-[CH3;D1;+0:8])-[CH3;D1;+0:9].[#7:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C;H0;D4;+0:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[CH3;D1;+0:17].[C:18]-[C:19]-[NH;D2;+0:20]-[#16:21](=[O;D1;H0:22])(=... | null | [] | null | null | null | null | A solution of Intermediate 1 (640 mg), 1,1′-azobis(N,N-dimethylformamide) (1200 mg, Aldrich or prepared according to Chemistry Letters, 539 (1994)) and 3-phenyl-1-propanol (710 μl, Tokyo Kasei Kogyo) in tetrahydrofuran (30 ml) was added with tri(n-butyl)phosphine (1.75 ml, Tokyo Kasei Kogyo) with stirring and ice cooli... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonamide.Ether.Diazene.Tertiary amide.Tertiary amide.Boc | Ether.Tertiary amine.Boc | null | c1ccccc1 | c1ccccc1.c1ccc2cnccc2c1 | HO- | O1CCCC1 | null | null | CC(C)(C)OC(=O)NCCCNS(=O)(=O)c1cccc2cnccc12.CCCCP(CCCC)CCCC.CN(C)C(=O)N=NC(=O)N(C)C>O1CCCC1>CC(C)(C)OC(=O)NCCCN(CCCc1ccccc1)S(=O)(=O)c1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-62100151a08f44888e9b9f008aa8d719 | CC(C)(C)OC(=O)NCCCN(CCCc1ccccc1)S(=O)(=O)c1cccc2cnccc12>>NCCCN(CCCc1ccccc1)S(=O)(=O)c1cccc2cnccc12 | C(C)(C)(C)OC(=O)NCCCN(CCCC1=CC=CC=C1)S(=O)(=O)C1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)S(=O)(=O)N(CCCN)CCCC1=CC=CC=C1 | CC(C)(C)OC(=O)[NH:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][c:23]2[cH:24][n:25][cH:26][cH:27][c:28]12>>[NH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[S:16](=[O:17... | CC(C)(C)OC(=O)NCCCN(CCCc1ccccc1)S(=O)(=O)c1cccc2cnccc12 | NCCCN(CCCc1ccccc1)S(=O)(=O)c1cccc2cnccc12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=S(=O)(NCCCc1ccccc1)c1cccc2cnccc12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | 25 | MINUTE | Intermediate 2 (913 mg) was added with 10% hydrogen chloride/methanol solution (18 ml, Tokyo Kasei Kogyo) at room temperature and stirred for 25 minutes under reflux by heating. After the reaction, the solvent was evaporated under reduced pressure, and the residue was crystallized from a mixed solvent of methanol and d... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2cnccc2c1 | HO- | null | null | 0.416667 | CC(C)(C)OC(=O)NCCCN(CCCc1ccccc1)S(=O)(=O)c1cccc2cnccc12>>NCCCN(CCCc1ccccc1)S(=O)(=O)c1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b5e351201461494c8b84873e8fe9cd2a | CC(C)(C)OC(=O)NCCCN(CCc1cccs1)S(=O)(=O)c1cccc2cnccc12>>NCCCN(CCc1cccs1)S(=O)(=O)c1cccc2cnccc12 | C(C)(C)(C)OC(=O)NCCCN(CCC=1SC=CC1)S(=O)(=O)C1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)S(=O)(=O)N(CCCN)CCC=1SC=CC1 | CC(C)(C)OC(=O)[NH:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][s:13]1)[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19][cH:20][c:21]2[cH:22][n:23][cH:24][cH:25][c:26]12>>[NH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][s:13]1)[S:14](=[O:15])(=[O:16])[c:17]1[cH:18][cH:19]... | CC(C)(C)OC(=O)NCCCN(CCc1cccs1)S(=O)(=O)c1cccc2cnccc12 | NCCCN(CCc1cccs1)S(=O)(=O)c1cccc2cnccc12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=S(=O)(NCCc1cccs1)c1cccc2cnccc12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 3 (238 mg) and 10% hydrogen chloride/methanol solution (5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with meth... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccsc1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NCCCN(CCc1cccs1)S(=O)(=O)c1cccc2cnccc12>>NCCCN(CCc1cccs1)S(=O)(=O)c1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-40e9753b7e624fac9a959e0125d91815 | CC(C)(C)OC(=O)NCCCN(CCCCc1ccccc1)S(=O)(=O)c1cccc2cnccc12>>NCCCN(CCCCc1ccccc1)S(=O)(=O)c1cccc2cnccc12 | C(C)(C)(C)OC(=O)NCCCN(CCCCC1=CC=CC=C1)S(=O)(=O)C1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)S(=O)(=O)N(CCCN)CCCCC1=CC=CC=C1 | CC(C)(C)OC(=O)[NH:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][cH:23][c:24]2[cH:25][n:26][cH:27][cH:28][c:29]12>>[NH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16... | CC(C)(C)OC(=O)NCCCN(CCCCc1ccccc1)S(=O)(=O)c1cccc2cnccc12 | NCCCN(CCCCc1ccccc1)S(=O)(=O)c1cccc2cnccc12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=S(=O)(NCCCCc1ccccc1)c1cccc2cnccc12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 6 (249 mg) and 10% hydrogen chloride/methanol solution (5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with meth... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NCCCN(CCCCc1ccccc1)S(=O)(=O)c1cccc2cnccc12>>NCCCN(CCCCc1ccccc1)S(=O)(=O)c1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a776e1ae388e4dcfab81dc757e40f082 | Cc1cncc2cccc(S(=O)(=O)N(CCCNC(=O)OC(C)(C)C)CCCc3ccccc3)c12>>Cc1cncc2cccc(S(=O)(=O)N(CCCN)CCCc3ccccc3)c12 | C(C)(C)(C)OC(=O)NCCCN(CCCC1=CC=CC=C1)S(=O)(=O)C1=C2C(=CN=CC2=CC=C1)C.Cl.CO>>Cl.CC1=CN=CC2=CC=CC(=C12)S(=O)(=O)N(CCCN)CCCC1=CC=CC=C1 | CC(C)(C)OC(=O)[NH:18][CH2:17][CH2:16][CH2:15][N:14]([S:11]([c:10]1[cH:9][cH:8][cH:7][c:6]2[cH:5][n:4][cH:3][c:2]([CH3:1])[c:28]21)(=[O:12])=[O:13])[CH2:19][CH2:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([S:11](=[O:12])(=[O:13])[N:14]([CH2:15][CH2... | Cc1cncc2cccc(S(=O)(=O)N(CCCNC(=O)OC(C)(C)C)CCCc3ccccc3)c12 | Cc1cncc2cccc(S(=O)(=O)N(CCCN)CCCc3ccccc3)c12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=S(=O)(NCCCc1ccccc1)c1cccc2cnccc12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (5° C., 2 hours) by using Intermediate 8 (87 mg) and 10% hydrogen chloride/methanol solution (5 ml). The reaction mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure. The residue was added with methanol (1... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1.c1ccccc1 | HO- | null | null | null | Cc1cncc2cccc(S(=O)(=O)N(CCCNC(=O)OC(C)(C)C)CCCc3ccccc3)c12>>Cc1cncc2cccc(S(=O)(=O)N(CCCN)CCCc3ccccc3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-157b347806e5402d819b7c9214a3f0d4 | CC(C)(C)OC(=O)NCCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2cnccc12>>NCCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2cnccc12 | C(C)(C)(C)OC(=O)NCCCN(CCS(=O)(=O)C1=CC=CC=C1)S(=O)(=O)C1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)S(=O)(=O)N(CCCN)CCS(=O)(=O)C1=CC=CC=C1 | CC(C)(C)OC(=O)[NH:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[S:18](=[O:19])(=[O:20])[c:21]1[cH:22][cH:23][cH:24][c:25]2[cH:26][n:27][cH:28][cH:29][c:30]12>>[NH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:... | CC(C)(C)OC(=O)NCCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2cnccc12 | NCCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2cnccc12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=S(=O)(CCNS(=O)(=O)c1cccc2cnccc12)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 9 (266 mg) and 10% hydrogen chloride/methanol solution (5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with meth... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NCCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2cnccc12>>NCCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-87611e49e57f41e0aa291dec7a4e4ee9 | CC(C)(C)OC(=O)NCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2cnccc12>>NCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2cnccc12 | C(C)(C)(C)OC(=O)NCCN(CCS(=O)(=O)C1=CC=CC=C1)S(=O)(=O)C1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)S(=O)(=O)N(CCN)CCS(=O)(=O)C1=CC=CC=C1 | CC(C)(C)OC(=O)[NH:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][cH:23][c:24]2[cH:25][n:26][cH:27][cH:28][c:29]12>>[NH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16... | CC(C)(C)OC(=O)NCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2cnccc12 | NCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2cnccc12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=S(=O)(CCNS(=O)(=O)c1cccc2cnccc12)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 11 (260 mg) and 10% hydrogen chloride/methanol solution (5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with met... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2cnccc12>>NCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0b98f7d580184ebbb6b7dbce359be919 | CC(C)(C)OC(=O)NCCCN.O=S(=O)(Cl)c1cccc2c(Cl)nccc12>>CC(C)(C)OC(=O)NCCCNS(=O)(=O)c1cccc2c(Cl)nccc12 | Cl.ClC1=NC=CC2=C(C=CC=C12)S(=O)(=O)Cl.C(C)(C)(C)OC(NCCCN)=O.C(C)N(CC)CC.ClC1=NC=CC2=C(C=CC=C12)S(=O)(=O)Cl>>C(C)(C)(C)OC(=O)NCCCNS(=O)(=O)C1=C2C=CN=C(C2=CC=C1)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][NH2:12].Cl[S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18][cH:19][c:20]2[c:21]([Cl:22])[n:23][cH:24][cH:25][c:26]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][NH:12][S:13](=[O:14])(=[O:15])[c:16]1[cH:17][cH:18... | CC(C)(C)OC(=O)NCCCN.O=S(=O)(Cl)c1cccc2c(Cl)nccc12 | CC(C)(C)OC(=O)NCCCNS(=O)(=O)c1cccc2c(Cl)nccc12 | null | null | ClCCl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccc2cnccc2c1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8]-[NH2;D1;+0:9]>>[C:7]-[C:8]-[NH;D2;+0:9]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 20 | HOUR | According to the method of Example 1, Step A, a solution of N-(3-aminopropyl)carbamic acid tert-butyl ester (383 mg) and triethylamine (335 μl) in dichloromethane (3 ml) was added with a solution of (1-chloro-5-isoquinolyl)sulfonyl chloride (524 mg, prepared from (1-chloro-5-isoquinolyl)sulfonyl chloride hydrochloride ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccc2cnccc2c1 | HCl | ClCCl | null | 20 | CC(C)(C)OC(=O)NCCCN.O=S(=O)(Cl)c1cccc2c(Cl)nccc12>ClCCl>CC(C)(C)OC(=O)NCCCNS(=O)(=O)c1cccc2c(Cl)nccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1f0fc8e12b234911a16444002c85ac20 | CC(C)(C)OC(=O)NCCCN(CCCc1ccccc1)S(=O)(=O)c1cccc2c(N)nccc12>>NCCCN(CCCc1ccccc1)S(=O)(=O)c1cccc2c(N)nccc12 | NC1=NC=CC2=C(C=CC=C12)S(=O)(=O)N(CCCNC(=O)OC(C)(C)C)CCCC1=CC=CC=C1.Cl.CO>>Cl.NC1=NC=CC2=C(C=CC=C12)S(=O)(=O)N(CCCN)CCCC1=CC=CC=C1 | CC(C)(C)OC(=O)[NH:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[S:16](=[O:17])(=[O:18])[c:19]1[cH:20][cH:21][cH:22][c:23]2[c:24]([NH2:25])[n:26][cH:27][cH:28][c:29]12>>[NH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:7][CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[S:1... | CC(C)(C)OC(=O)NCCCN(CCCc1ccccc1)S(=O)(=O)c1cccc2c(N)nccc12 | NCCCN(CCCc1ccccc1)S(=O)(=O)c1cccc2c(N)nccc12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=S(=O)(NCCCc1ccccc1)c1cccc2cnccc12 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (5° C., 2 hours) by using Intermediate 14 (125 mg) and 10% hydrogen chloride/methanol solution (2.5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with me... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NCCCN(CCCc1ccccc1)S(=O)(=O)c1cccc2c(N)nccc12>>NCCCN(CCCc1ccccc1)S(=O)(=O)c1cccc2c(N)nccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cfd70b3b3b30460cbdf9d354bc36adca | CC(C)(C)OC(=O)NCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2c(N)nccc12>>NCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2c(N)nccc12 | NC1=NC=CC2=C(C=CC=C12)S(=O)(=O)N(CCNC(=O)OC(C)(C)C)CCS(=O)(=O)C1=CC=CC=C1.Cl.CO>>Cl.NC1=NC=CC2=C(C=CC=C12)S(=O)(=O)N(CCN)CCS(=O)(=O)C1=CC=CC=C1 | CC(C)(C)OC(=O)[NH:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[S:17](=[O:18])(=[O:19])[c:20]1[cH:21][cH:22][cH:23][c:24]2[c:25]([NH2:26])[n:27][cH:28][cH:29][c:30]12>>[NH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][S:8](=[O:9])(=[O:10])[c:11]1[cH:12][cH:13][cH:14][cH:... | CC(C)(C)OC(=O)NCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2c(N)nccc12 | NCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2c(N)nccc12 | null | null | C(C)OCC | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=S(=O)(CCNS(=O)(=O)c1cccc2cnccc12)c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 17 (134 mg) and 10% hydrogen chloride/methanol solution (2.5 ml). The reaction mixture was cooled to room temperature and then added with diethyl ether (2.5 ml). The deposited precipitates were collected by ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2cnccc2c1 | HO- | C(C)OCC | null | null | CC(C)(C)OC(=O)NCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2c(N)nccc12>C(C)OCC>NCCN(CCS(=O)(=O)c1ccccc1)S(=O)(=O)c1cccc2c(N)nccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-881ac3f56ed04e33b46fda327ae9d93f | CC(C)(C)OC(=O)NCCCO.Oc1cccc2c(Cl)nccc12>>CC(C)(C)OC(=O)NCCCOc1cccc2c(Cl)nccc12 | C(CCC)P(CCCC)CCCC.ClC1=NC=CC2=C(C=CC=C12)O.C(C)(C)(C)OC(NCCCO)=O.N(=NC(=O)N(C)C)C(=O)N(C)C>>C(C)(C)(C)OC(=O)NCCCOC1=C2C=CN=C(C2=CC=C1)Cl | O[CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[OH:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[c:18]([Cl:19])[n:20][cH:21][cH:22][c:23]12>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[c:18]([Cl:19])[n:20][cH:21][cH:22][... | CC(C)(C)OC(=O)NCCCO.Oc1cccc2c(Cl)nccc12 | CC(C)(C)OC(=O)NCCCOc1cccc2c(Cl)nccc12 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc2cnccc2c1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 24 | HOUR | A suspension of 1-chloro-5-hydroxyisoquinoline (539 mg, synthesized according to the method described in a reference (Georgian, V. et al., J. Org. Chem., 27, 4571 (1962))), (3-hydroxypropyl)carbamic acid tert-butyl ester (1.58 g, Tokyo Kasei Kogyo) and 1,1′-azobis(N,N-dimethylformamide) (1.55 g) in tetrahydrofuran (8 m... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccc2cnccc2c1 | HO- | O1CCCC1 | null | 24 | CC(C)(C)OC(=O)NCCCO.Oc1cccc2c(Cl)nccc12>O1CCCC1>CC(C)(C)OC(=O)NCCCOc1cccc2c(Cl)nccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e01521f8a6a49748b5268aa0846e201 | CC(C)(C)OC(=O)NCCCOc1cccc2c(Cl)nccc12>>Cl.NCCCOc1cccc2c(N)nccc12 | C(C)(C)(C)OC(=O)NCCCOC1=C2C=CN=C(C2=CC=C1)Cl.C(C)(C)(C)OC(=O)NCCCOC1=C2C=CN=C(C2=CC=C1)Cl.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.COC1=CC=C(CN)C=C1.CC(C)([O-])C.[Na+]>>Cl.NC1=NC=CC2=C(C=CC=C12)OCCCN | CC(C)(C)OC(=O)[NH:2][CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([Cl:1])[n:14][cH:15][cH:16][c:17]12>>[ClH:1].[NH2:2][CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([NH2:13])[n:14][cH:15][cH:16][c:17]12 | CC(C)(C)OC(=O)NCCCOc1cccc2c(Cl)nccc12 | Cl.NCCCOc1cccc2c(N)nccc12 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C(C)(=O)OCC.C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | ca47f18fdd8a333ba739357322d7eea24bf7b08489a81c071de05fff408e8608 | 08bb0e341d3145616cc2674a463d3dbf2fc29e30c174b6945e30ce804e6809c3 | c1ccc2cnccc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].[Cl;H0;D1;+0:4]-[c;H0;D3;+0:5](:[#7;a:6]:[c:7]):[c:8](:[c:9]):[c:10]>>[C:3]-[C:2]-[NH2;D1;+0:1].[N;D1;H2:11]-[c;H0;D3;+0:5](:[#7;a:6]:[c:7]):[c:8](:[c:9]):[c:10].[ClH;D0;+0:4] | null | [] | 80 | CELSIUS | null | null | The title compound was synthesized from Intermediate 18 according to the method described in a reference (Buchwald, S. L., J. Org. Chem., 65, 1158 (2000)). That is, a suspension of Intermediate 18 (674 mg), tris (dibenzylideneacetone)dipalladium(0) (92 mg, Aldrich), 2-(di-tert-butylphosphino)biphenyl (119 mg, Strem Che... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carbamic ester.Ether.Boc | Primary amine.Primary amine | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | HO- | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C(C)(=O)OCC.C1(=CC=CC=C1)C | 80 | null | CC(C)(C)OC(=O)NCCCOc1cccc2c(Cl)nccc12>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C(C)(=O)OCC.C1(=CC=CC=C1)C>Cl.NCCCOc1cccc2c(N)nccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-40b53d9bfdf444818e70852330749f6c | CC(C)(C)OC(=O)NCCCOc1cccc2c(N)nccc12>>NCCCOc1cccc2c(N)nccc12 | C(C)(C)(C)OC(=O)NCCCOC1=C2C=CN=C(C2=CC=C1)N.Cl.CO>>Cl.NC1=NC=CC2=C(C=CC=C12)OCCCN | CC(C)(C)OC(=O)[NH:2][CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([NH2:13])[n:14][cH:15][cH:16][c:17]12>>[NH2:2][CH2:3][CH2:4][CH2:5][O:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[c:12]([NH2:13])[n:14][cH:15][cH:16][c:17]12 | CC(C)(C)OC(=O)NCCCOc1cccc2c(N)nccc12 | NCCCOc1cccc2c(N)nccc12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc2cnccc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 20 (159 mg) and 10% hydrogen chloride/methanol solution (2.5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with m... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NCCCOc1cccc2c(N)nccc12>>NCCCOc1cccc2c(N)nccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-31ed84e073364a278a09080c0b0a2456 | CC(C)(C)OC(=O)N1CCCC(COc2cccc3c(N)nccc23)C1>>Nc1nccc2c(OCC3CCCNC3)cccc12 | C(C)(C)(C)OC(=O)N1CC(CCC1)COC1=C2C=CN=C(C2=CC=C1)N.Cl.CO>>Cl.NC1=NC=CC2=C(C=CC=C12)OCC1CNCCC1 | CC(C)(C)OC(=O)[N:15]1[CH2:14][CH2:13][CH2:12][CH:11]([CH2:10][O:9][c:8]2[c:7]3[cH:6][cH:5][n:4][c:3]([NH2:2])[c:20]3[cH:19][cH:18][cH:17]2)[CH2:16]1>>[NH2:2][c:3]1[n:4][cH:5][cH:6][c:7]2[c:8]([O:9][CH2:10][CH:11]3[CH2:12][CH2:13][CH2:14][NH:15][CH2:16]3)[cH:17][cH:18][cH:19][c:20]12 | CC(C)(C)OC(=O)N1CCCC(COc2cccc3c(N)nccc23)C1 | Nc1nccc2c(OCC3CCCNC3)cccc12 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(OCC2CCCNC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 23 (179 mg) and 10% hydrogen chloride/methanol solution (2.5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with m... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCCC(COc2cccc3c(N)nccc23)C1>>Nc1nccc2c(OCC3CCCNC3)cccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-236c7339795b45e393f5e303add9f945 | Brc1cccc2cnccc12.CC(C)(C)OC(=O)NCCN>>CC(C)(C)OC(=O)NCCNc1cccc2cnccc12 | BrC1=C2C=CN=CC2=CC=C1.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.C(C)(C)(C)OC(NCCN)=O.CC(C)([O-])C.[Na+]>>C(C)(C)(C)OC(=O)NCCNC1=C2C=CN=CC2=CC=C1 | Br[c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17][n:18][cH:19][cH:20][c:21]12.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][NH2:11]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][NH:11][c:12]1[cH:13][cH:14][cH:15][c:16]2[cH:17][n:18][cH:19][cH:20][c:21]12 | Brc1cccc2cnccc12.CC(C)(C)OC(=O)NCCN | CC(C)(C)OC(=O)NCCNc1cccc2cnccc12 | null | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | C(C)(=O)OCC.C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 17c3dbb58f19c559a89452c2c52a32d81319b5dd6d11e225611cc478eba61c1b | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2cnccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1.[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | 70 | [{"value": 70.0, "product": "C(C)(C)(C)OC(=O)NCCNC1=C2C=CN=CC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | Under nitrogen atmosphere, a suspension of 5-bromoisoquinoline (416 mg, Spex), tris(dibenzylideneacetone)dipalladium(0) (92 mg), 2-(di-tert-butylphosphino)biphenyl (119 mg), N-(2-aminoethyl)carbamic acid tert-butyl ester (385 mg) and sodium tert-butoxide (269 mg) in toluene (5 ml) was stirred with heating at 80° C. for... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | HBr | C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C(C)(=O)OCC.C1(=CC=CC=C1)C | 80 | null | Brc1cccc2cnccc12.CC(C)(C)OC(=O)NCCN>C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd].C(C)(=O)OCC.C1(=CC=CC=C1)C>CC(C)(C)OC(=O)NCCNc1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-83ccd6a730cf4a3f904464d1133a0cd4 | CC(C)(C)OC(=O)NCCNc1cccc2cnccc12>>NCCNc1cccc2cnccc12 | C(C)(C)(C)OC(=O)NCCNC1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)NCCN | CC(C)(C)OC(=O)[NH:2][CH2:3][CH2:4][NH:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[cH:11][n:12][cH:13][cH:14][c:15]12>>[NH2:2][CH2:3][CH2:4][NH:5][c:6]1[cH:7][cH:8][cH:9][c:10]2[cH:11][n:12][cH:13][cH:14][c:15]12 | CC(C)(C)OC(=O)NCCNc1cccc2cnccc12 | NCCNc1cccc2cnccc12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc2cnccc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 27 (287 mg) and 10% hydrogen chloride/methanol solution (5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with met... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NCCNc1cccc2cnccc12>>NCCNc1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5d0c38bbf7054bdc8ce5961cd8721103 | CC(C)(C)OC(=O)NCCCNc1cccc2cnccc12>>NCCCNc1cccc2cnccc12 | C(C)(C)(C)OC(=O)NCCCNC1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)NCCCN | CC(C)(C)OC(=O)[NH:2][CH2:3][CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[cH:12][n:13][cH:14][cH:15][c:16]12>>[NH2:2][CH2:3][CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[cH:12][n:13][cH:14][cH:15][c:16]12 | CC(C)(C)OC(=O)NCCCNc1cccc2cnccc12 | NCCCNc1cccc2cnccc12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc2cnccc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 28 (301 mg) and 10% hydrogen chloride/methanol solution (5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with met... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NCCCNc1cccc2cnccc12>>NCCCNc1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-34859159c1f24492b072bc7bfbc36a45 | Brc1cccc2cnccc12.CN(CCCN)C(=O)OC(C)(C)C>>CN(CCCNc1cccc2cnccc12)C(=O)OC(C)(C)C | BrC1=C2C=CN=CC2=CC=C1.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.C(C)(C)(C)OC(N(C)CCCN)=O.CC(C)([O-])C.[Na+]>>C(C)(C)(C)OC(=O)N(CCCNC1=C2C=CN=CC2=CC=C1)C | Br[c:7]1[cH:8][cH:9][cH:10][c:11]2[cH:12][n:13][cH:14][cH:15][c:16]12.[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][NH2:6])[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23]>>[CH3:1][N:2]([CH2:3][CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[cH:12][n:13][cH:14][cH:15][c:16]12)[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:... | Brc1cccc2cnccc12.CN(CCCN)C(=O)OC(C)(C)C | CN(CCCNc1cccc2cnccc12)C(=O)OC(C)(C)C | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 17c3dbb58f19c559a89452c2c52a32d81319b5dd6d11e225611cc478eba61c1b | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2cnccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1.[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | 85.1 | [{"value": 85.1, "product": "C(C)(C)(C)OC(=O)N(CCCNC1=C2C=CN=CC2=CC=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | Under nitrogen atmosphere, a suspension of 5-bromoisoquinoline (252 mg), tris(dibenzylideneacetone)palladium(0) (59 mg), 2-(di-tert-butylphosphino)biphenyl (74 mg), (3-aminopropyl)methylcarbamic acid tert-butyl ester (274 mg, Asta Tech), and sodium tert-butoxide (163 mg) in toluene was stirred with heating at 70° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | HBr | C1(=CC=CC=C1)C | 70 | null | Brc1cccc2cnccc12.CN(CCCN)C(=O)OC(C)(C)C>C1(=CC=CC=C1)C>CN(CCCNc1cccc2cnccc12)C(=O)OC(C)(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e9e223d3e3e74eb7b824227dc02c0a1d | CN(CCCNc1cccc2cnccc12)C(=O)OC(C)(C)C>>CNCCCNc1cccc2cnccc12 | C(C)(C)(C)OC(=O)N(CCCNC1=C2C=CN=CC2=CC=C1)C.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)NCCCNC | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[cH:12][n:13][cH:14][cH:15][c:16]12>>[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][NH:6][c:7]1[cH:8][cH:9][cH:10][c:11]2[cH:12][n:13][cH:14][cH:15][c:16]12 | CN(CCCNc1cccc2cnccc12)C(=O)OC(C)(C)C | CNCCCNc1cccc2cnccc12 | null | null | null | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc2cnccc2c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (room temperature, 31 hours) by using Intermediate 29 (325 mg) and 10% hydrogen chloride/methanol solution (5 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (1 ml) and diethyl ether (3 ml). The depo... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | c1ccc2cnccc2c1 | HO- | null | null | null | CN(CCCNc1cccc2cnccc12)C(=O)OC(C)(C)C>>CNCCCNc1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-672a2fed6b53437e84c0e43685bb65b1 | CC(C)(C)OC(=O)NCCCCNc1cccc2cnccc12>>NCCCCNc1cccc2cnccc12 | C(C)(C)(C)OC(=O)NCCCCNC1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)NCCCCN | CC(C)(C)OC(=O)[NH:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][n:14][cH:15][cH:16][c:17]12>>[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][c:8]1[cH:9][cH:10][cH:11][c:12]2[cH:13][n:14][cH:15][cH:16][c:17]12 | CC(C)(C)OC(=O)NCCCCNc1cccc2cnccc12 | NCCCCNc1cccc2cnccc12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc2cnccc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 30 (316 mg) and 10% hydrogen chloride/methanol solution (5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with met... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NCCCCNc1cccc2cnccc12>>NCCCCNc1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-600f4b91275841b0837efb247cf9997c | Brc1cccc2cnccc12.CC(C)(C)OC(=O)NCCCCCN>>CC(C)(C)OC(=O)NCCCCCNc1cccc2cnccc12 | BrC1=C2C=CN=CC2=CC=C1.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.C(C)(C)(C)OC(NCCCCCN)=O.CC(C)([O-])C.[Na+]>>C(C)(C)(C)OC(=O)NCCCCCNC1=C2C=CN=CC2=CC=C1 | Br[c:15]1[cH:16][cH:17][cH:18][c:19]2[cH:20][n:21][cH:22][cH:23][c:24]12.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][c:15]1[cH:16][cH:17][cH:18][c:19]2[cH:20][n... | Brc1cccc2cnccc12.CC(C)(C)OC(=O)NCCCCCN | CC(C)(C)OC(=O)NCCCCCNc1cccc2cnccc12 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 17c3dbb58f19c559a89452c2c52a32d81319b5dd6d11e225611cc478eba61c1b | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2cnccc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1.[C:10]-[C:11]-[NH2;D1;+0:12]>>[C:10]-[C:11]-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1 | 84.3 | [{"value": 84.3, "product": "C(C)(C)(C)OC(=O)NCCCCCNC1=C2C=CN=CC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | Under nitrogen atmosphere, a suspension of 5-bromoisoquinoline (245 mg), tris(dibenzylideneacetone)palladium(0) (56 mg), 2-(di-tert-butylphosphino)biphenyl (69 mg), N-(5-aminopentyl)carbamic acid tert-butyl ester (282 mg, Tokyo Kasei Kogyo) and sodium tert-butoxide (160 mg) in toluene was stirred with heating at 70° C.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | HBr | C1(=CC=CC=C1)C | 70 | null | Brc1cccc2cnccc12.CC(C)(C)OC(=O)NCCCCCN>C1(=CC=CC=C1)C>CC(C)(C)OC(=O)NCCCCCNc1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-95aa8b8184824c4f92502d147d13a2fb | CC(C)(C)OC(=O)NCCCCCNc1cccc2cnccc12>>NCCCCCNc1cccc2cnccc12 | C(C)(C)(C)OC(=O)NCCCCCNC1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)NCCCCCN | CC(C)(C)OC(=O)[NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][n:15][cH:16][cH:17][c:18]12>>[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][NH:8][c:9]1[cH:10][cH:11][cH:12][c:13]2[cH:14][n:15][cH:16][cH:17][c:18]12 | CC(C)(C)OC(=O)NCCCCCNc1cccc2cnccc12 | NCCCCCNc1cccc2cnccc12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc2cnccc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | null | [] | null | null | null | null | According to the method of the above Example, deprotection was performed (room temperature, 31 hours) by using Intermediate 31 (327 mg) and 10% hydrogen chloride/methanol solution (5 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (1 ml) and diethyl ether (3 ml). The depo... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NCCCCCNc1cccc2cnccc12>>NCCCCCNc1cccc2cnccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6faf4ab15932459f9790d3c18a3b64cc | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cnccc23)CC1>>c1cc(NC2CCNCC2)c2ccncc2c1 | C1=NC=CC2=C(C=CC=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)NC1CCNCC1 | CC(C)(C)OC(=O)[N:9]1[CH2:8][CH2:7][CH:6]([NH:5][c:4]2[cH:3][cH:2][cH:18][c:17]3[c:12]2[cH:13][cH:14][n:15][cH:16]3)[CH2:11][CH2:10]1>>[cH:2]1[cH:3][c:4]([NH:5][CH:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[c:12]2[cH:13][cH:14][n:15][cH:16][c:17]2[cH:18]1 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cnccc23)CC1 | c1cc(NC2CCNCC2)c2ccncc2c1 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(NC2CCNCC2)c2ccncc2c1 | 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] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 32 (327 mg) and 10% hydrogen chloride/methanol solution (5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with met... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cnccc23)CC1>>c1cc(NC2CCNCC2)c2ccncc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-52248c0e52ae41509e95eacfd95e2764 | CC(C)(C)OC(=O)N1CCC(CNc2cccc3cnccc23)CC1>>c1cc(NCC2CCNCC2)c2ccncc2c1 | C(C)(C)(C)OC(=O)N1CCC(CC1)CNC1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)NCC1CCNCC1 | CC(C)(C)OC(=O)[N:10]1[CH2:9][CH2:8][CH:7]([CH2:6][NH:5][c:4]2[cH:3][cH:2][cH:19][c:18]3[c:13]2[cH:14][cH:15][n:16][cH:17]3)[CH2:12][CH2:11]1>>[cH:2]1[cH:3][c:4]([NH:5][CH2:6][CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[c:13]2[cH:14][cH:15][n:16][cH:17][c:18]2[cH:19]1 | CC(C)(C)OC(=O)N1CCC(CNc2cccc3cnccc23)CC1 | c1cc(NCC2CCNCC2)c2ccncc2c1 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(NCC2CCNCC2)c2ccncc2c1 | 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] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 33 (171 mg) and 10% hydrogen chloride/methanol solution (2.5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with m... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(CNc2cccc3cnccc23)CC1>>c1cc(NCC2CCNCC2)c2ccncc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-919d2c5e1db54d07986b3c573f3147b2 | CC(C)(C)OC(=O)N1CCCC(CNc2cccc3cnccc23)C1>>c1cc(NCC2CCCNC2)c2ccncc2c1 | C(C)(C)(C)OC(=O)N1CC(CCC1)CNC1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)NCC1CNCCC1 | CC(C)(C)OC(=O)[N:11]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:6][NH:5][c:4]2[cH:3][cH:2][cH:19][c:18]3[c:13]2[cH:14][cH:15][n:16][cH:17]3)[CH2:12]1>>[cH:2]1[cH:3][c:4]([NH:5][CH2:6][CH:7]2[CH2:8][CH2:9][CH2:10][NH:11][CH2:12]2)[c:13]2[cH:14][cH:15][n:16][cH:17][c:18]2[cH:19]1 | CC(C)(C)OC(=O)N1CCCC(CNc2cccc3cnccc23)C1 | c1cc(NCC2CCCNC2)c2ccncc2c1 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(NCC2CCCNC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:5]-[C:4]-[NH;D2;+0:1]-[C:2]-[C:3] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 34 (171 mg) and 10% hydrogen chloride/methanol solution (2.5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with m... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCCC(CNc2cccc3cnccc23)C1>>c1cc(NCC2CCCNC2)c2ccncc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d2ae7ccd3f25492baf70cc5fa51d6131 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](O)CC1.CS(=O)(=O)Cl>>CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](OS(C)(=O)=O)CC1 | O.CO.C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)O.CS(=O)(=O)Cl>>C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OS(=O)(=O)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([OH:13])[CH2:18][CH2:19]1.Cl[S:14]([CH3:15])(=[O:16])=[O:17]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([O:13][S:14]([CH3:15])(=[O:16])=[O:17])[CH2:18][CH2:19]1 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](O)CC1.CS(=O)(=O)Cl | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](OS(C)(=O)=O)CC1 | null | null | N1=CC=CC=C1 | Acylation | Formation of Sulfonic Esters | 641955d0081c80f158ce2aacd31873a3f3301c87ca0800cf263e288ba8390217 | 4f9373df8a11470603daf885a5777cebf95940370e32739263d35df0f171a0dd | C1CCCCC1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6](-[OH;D1;+0:7])-[C:8]>>[C:5]-[C:6](-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4])-[C:8] | null | [] | null | null | 15 | MINUTE | A solution of Intermediate 35 (90.3 g) in pyridine (415 ml) was added dropwise with methanesulfonyl chloride (42.4 ml) with stirring and ice cooling over 15 minutes and stirred with ice cooling for 30 minutes and at room temperature for 20 minutes. The reaction mixture was added with methanol (54.2 ml) to terminate the... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfonyl halide | Mesylate | null | null | C1CCCCC1 | HCl | N1=CC=CC=C1 | null | 0.25 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](O)CC1.CS(=O)(=O)Cl>N1=CC=CC=C1>CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](OS(C)(=O)=O)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b811f8e37f91454ca9c82dfe2654d854 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](OS(C)(=O)=O)CC1.C[Si](C)(C)N=[N+]=[N-]>>CC(C)(C)OC(=O)N[C@@H]1CC[C@H](N=[N+]=[N-])CC1 | O.C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)OS(=O)(=O)C.C[Si](C)(C)N=[N+]=[N-].[F-].[Cs+]>>C(C)(C)(C)OC(=O)N[C@H]1CC[C@H](CC1)N=[N+]=[N-] | CS(=O)(=O)O[C@H:12]1[CH2:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:17][CH2:16]1.C[Si](C)(C)[N:13]=[N+:14]=[N-:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@@H:12]([N:13]=[N+:14]=[N-:15])[CH2:16][CH2:17]1 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](OS(C)(=O)=O)CC1.C[Si](C)(C)N=[N+]=[N-] | CC(C)(C)OC(=O)N[C@@H]1CC[C@H](N=[N+]=[N-])CC1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | d3ae5583ed85436d254cdb02077da151826687662d071f700d766a96fefbcdac | 07318ec98fcf637ef5b643775774166eb320ca1ca12ae991c23914bca80bab51 | C1CCCCC1 | C-S(=O)(=O)-O-[C@@H;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].C-[Si](-C)(-C)-[N;H0;D2;+0:6]=[#7;+:7]=[N;-;D1;H0:8]>>[C:3]-[C:2]-[C@@H;D3;+0:1](-[N;H0;D2;+0:6]=[#7;+:7]=[N;-;D1;H0:8])-[C:4]-[C:5] | null | [] | null | null | null | null | A solution of Intermediate 36 (196 g) and trimethylsilyl azide (283 ml, Tokyo Kasei Kogyo) in dimethylformamide (667 ml) was added with cesium fluoride (305 g, Wako Pure Chemical Industries) with stirring and stirred at 70° C. for 4 days. The reaction mixture was cooled to room temperature and then added twice with wat... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Azide.Silyl protective group | Azide | C1CCCCC1 | C1CCCCC1 | C1CCCCC1 | MsOH.HO- | CN(C=O)C | null | null | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](OS(C)(=O)=O)CC1.C[Si](C)(C)N=[N+]=[N-]>CN(C=O)C>CC(C)(C)OC(=O)N[C@@H]1CC[C@H](N=[N+]=[N-])CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fea9acd2f75549b088952fd82f2bc28a | CC(C)(C)OC(=O)N[C@@H]1CC[C@H](N=[N+]=[N-])CC1>>CC(C)(C)OC(=O)N[C@@H]1CC[C@H](N)CC1 | C(C)(C)(C)OC(=O)N[C@H]1CC[C@H](CC1)N=[N+]=[N-]>>C(C)(C)(C)OC(=O)N[C@H]1CC[C@H](CC1)N | [N-]=[N+]=[N:13][C@@H:12]1[CH2:11][CH2:10][C@H:9]([NH: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])[NH:8][C@H:9]1[CH2:10][CH2:11][C@@H:12]([NH2:13])[CH2:14][CH2:15]1 | CC(C)(C)OC(=O)N[C@@H]1CC[C@H](N=[N+]=[N-])CC1 | CC(C)(C)OC(=O)N[C@@H]1CC[C@H](N)CC1 | null | [Pd] | C(C)(=O)OCC | Reduction | Azide to amine reduction (Staudinger) | 4c9e4990dae2bb965dec06bd45e318560989ee3681b61e443f7aa363b7cfa222 | cd009d687d606bf351eac9390a176d16be38f2c8216a599b398641009c215027 | C1CCCCC1 | [C:1]-[C:2](-[N;H0;D2;+0:3]=[N+]=[N-])-[C:4]>>[C:1]-[C:2](-[NH2;D1;+0:3])-[C:4] | 36.2 | [{"value": 36.2, "product": "C(C)(C)(C)OC(=O)N[C@H]1CC[C@H](CC1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The roughly purified product of Intermediate 37 (142 g) was reduced by hydrogenation at room temperature for 9 hours by using 10% Pd/C (7.1 g) and ethyl acetate solution (1.42 l) under hydrogen atmosphere of 1 atm. The palladium catalyst was removed by filtration, and the solvent was evaporated under reduced pressure. ... | 10.6084/m9.figshare.5104873.v1 | null | Azide | Primary amine | null | null | C1CCCCC1 | Other | [Pd].C(C)(=O)OCC | null | null | CC(C)(C)OC(=O)N[C@@H]1CC[C@H](N=[N+]=[N-])CC1>[Pd].C(C)(=O)OCC>CC(C)(C)OC(=O)N[C@@H]1CC[C@H](N)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-62ca8446a3a044da8763ed93973f3667 | Brc1cccc2cnccc12.CC(C)(C)OC(=O)N[C@@H]1CC[C@H](N)CC1>>CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 | BrC1=C2C=CN=CC2=CC=C1.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.C(C)(C)(C)OC(=O)N[C@H]1CC[C@H](CC1)N.CC(C)([O-])C.[Na+]>>C(C)(C)(C)OC(=O)N[C@@H]1CC[C@@H](CC1)NC1=C2C=CN=CC2=CC=C1 | Br[c:14]1[cH:15][cH:16][cH:17][c:18]2[cH:19][n:20][cH:21][cH:22][c:23]12.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@@H:12]([NH2:13])[CH2:24][CH2:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@@H:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][c:18]3[... | Brc1cccc2cnccc12.CC(C)(C)OC(=O)N[C@@H]1CC[C@H](N)CC1 | CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 17c3dbb58f19c559a89452c2c52a32d81319b5dd6d11e225611cc478eba61c1b | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(NC2CCCCC2)c2ccncc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1.[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13]>>[C:10]-[C:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1)-[C:13] | 77.1 | [{"value": 77.1, "product": "C(C)(C)(C)OC(=O)N[C@@H]1CC[C@@H](CC1)NC1=C2C=CN=CC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | Under nitrogen atmosphere, a suspension of 5-bromoisoquinoline (253 mg), tris(dibenzylideneacetone)palladium(0) (58 mg), 2-(di-tert-butylphosphino)biphenyl (74 mg), Intermediate 38 (311 mg) and sodium tert-butoxide (165 mg) in toluene was stirred with heating at 70° C. for 3 hours. The reaction mixture was cooled to ro... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | C1CCCCC1.c1ccc2cnccc2c1 | HBr | C1(=CC=CC=C1)C | 70 | null | Brc1cccc2cnccc12.CC(C)(C)OC(=O)N[C@@H]1CC[C@H](N)CC1>C1(=CC=CC=C1)C>CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8889760d8b024e68bc4a6d002cdc2fe4 | CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Nc2cccc3cnccc23)CC1>>N[C@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@@H](CC1)NC1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)N[C@@H]1CC[C@@H](CC1)N | CC(C)(C)OC(=O)[NH:2][C@H:3]1[CH2:4][CH2:5][C@@H:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][n:14][cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1>>[NH2:2][C@H:3]1[CH2:4][CH2:5][C@@H:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][n:14][cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1 | CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 | N[C@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(NC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (room temperature, 31 hours) by using Intermediate 39 (214 mg) and 10% hydrogen chloride/methanol solution (5 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (1 ml) and diethyl ether (3 ml). The depo... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCCCC1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)N[C@H]1CC[C@@H](Nc2cccc3cnccc23)CC1>>N[C@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c614d1288161409291394e06408d3032 | Brc1cccc2cnccc12.CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](N)CC1>>CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 | BrC1=C2C=CN=CC2=CC=C1.C(C)(C)(C)P(C1=C(C=CC=C1)C1=CC=CC=C1)C(C)(C)C.C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)N.CC(C)([O-])C.[Na+]>>C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)NC1=C2C=CN=CC2=CC=C1 | Br[c:14]1[cH:15][cH:16][cH:17][c:18]2[cH:19][n:20][cH:21][cH:22][c:23]12.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([NH2:13])[CH2:24][CH2:25]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([NH:13][c:14]2[cH:15][cH:16][cH:17][c:18]3[cH... | Brc1cccc2cnccc12.CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](N)CC1 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | 17c3dbb58f19c559a89452c2c52a32d81319b5dd6d11e225611cc478eba61c1b | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(NC2CCCCC2)c2ccncc2c1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1.[C:10]-[C:11](-[NH2;D1;+0:12])-[C:13]>>[C:10]-[C:11](-[NH;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1)-[C:13] | 42 | [{"value": 42.0, "product": "C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)NC1=C2C=CN=CC2=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | Under nitrogen atmosphere, a suspension of 5-bromoisoquinoline (100 mg), tris(dibenzylideneacetone)palladium(0) (23 mg), 2-(di-tert-butylphosphino)biphenyl (29 mg), Intermediate 40 (122 mg) and sodium tert-butoxide (66 mg) in toluene was stirred with heating at 70° C. for 3.5 hours. The reaction mixture was cooled to r... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | C1CCCCC1.c1ccc2cnccc2c1 | HBr | C1(=CC=CC=C1)C | 70 | null | Brc1cccc2cnccc12.CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](N)CC1>C1(=CC=CC=C1)C>CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b3463dd1e45d4ff9a4d87ab1ddd0da87 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Nc2cccc3cnccc23)CC1>>N[C@@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 | C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)NC1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)N[C@@H]1CC[C@H](CC1)N | CC(C)(C)OC(=O)[NH:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][n:14][cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1>>[NH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][n:14][cH:15][cH:16][c:17]23)[CH2:18][CH2:19]1 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 | N[C@@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(NC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 1 hour) by using Intermediate 41 (69 mg) and 10% hydrogen chloride/methanol solution (4 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (0.5 ml) and diethyl ether (2 ml). The deposited preci... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCCCC1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](Nc2cccc3cnccc23)CC1>>N[C@@H]1CC[C@@H](Nc2cccc3cnccc23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4e36bb6d06d14714a6ce9ecc8076eb40 | CC(C)(C)OC(=O)NC1CCCC(Nc2cccc3cnccc23)C1>>NC1CCCC(Nc2cccc3cnccc23)C1 | C(C)(C)(C)OC(=O)NC1CC(CCC1)NC1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)NC1CC(CCC1)N | CC(C)(C)OC(=O)[NH:2][CH:3]1[CH2:4][CH2:5][CH2:6][CH:7]([NH:8][c:9]2[cH:10][cH:11][cH:12][c:13]3[cH:14][n:15][cH:16][cH:17][c:18]23)[CH2:19]1>>[NH2:2][CH:3]1[CH2:4][CH2:5][CH2:6][CH:7]([NH:8][c:9]2[cH:10][cH:11][cH:12][c:13]3[cH:14][n:15][cH:16][cH:17][c:18]23)[CH2:19]1 | CC(C)(C)OC(=O)NC1CCCC(Nc2cccc3cnccc23)C1 | NC1CCCC(Nc2cccc3cnccc23)C1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(NC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 43 (171 mg) and 10% hydrogen chloride/methanol solution (2.5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with m... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCCCC1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NC1CCCC(Nc2cccc3cnccc23)C1>>NC1CCCC(Nc2cccc3cnccc23)C1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c1897e61e42c4a49b6fe74b11d882df6 | CC(C)(C)OC(=O)NCc1cccc(CNc2cccc3cnccc23)c1>>NCc1cccc(CNc2cccc3cnccc23)c1 | C(C)(C)(C)OC(=O)NCC1=CC(=CC=C1)CNC1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)NCC1=CC(=CC=C1)CN | CC(C)(C)OC(=O)[NH:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][NH:10][c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][n:17][cH:18][cH:19][c:20]23)[cH:21]1>>[NH2:2][CH2:3][c:4]1[cH:5][cH:6][cH:7][c:8]([CH2:9][NH:10][c:11]2[cH:12][cH:13][cH:14][c:15]3[cH:16][n:17][cH:18][cH:19][c:20]23)[cH:21]1 | CC(C)(C)OC(=O)NCc1cccc(CNc2cccc3cnccc23)c1 | NCc1cccc(CNc2cccc3cnccc23)c1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(CNc2cccc3cnccc23)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[c:3]>>[NH2;D1;+0:1]-[C:2]-[c:3] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 44 (364 mg) and 10% hydrogen chloride/methanol solution (5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with met... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NCc1cccc(CNc2cccc3cnccc23)c1>>NCc1cccc(CNc2cccc3cnccc23)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-165bb2fd30774dcab9791f3bb61ece03 | CC(C)(C)OC(=O)N1CCC(Oc2cccc3cnccc23)CC1>>c1cc(OC2CCNCC2)c2ccncc2c1 | C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C2C=CN=CC2=CC=C1.Cl.CO>>Cl.C1=NC=CC2=C(C=CC=C12)OC1CCNCC1 | CC(C)(C)OC(=O)[N:9]1[CH2:8][CH2:7][CH:6]([O:5][c:4]2[cH:3][cH:2][cH:18][c:17]3[c:12]2[cH:13][cH:14][n:15][cH:16]3)[CH2:11][CH2:10]1>>[cH:2]1[cH:3][c:4]([O:5][CH:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[c:12]2[cH:13][cH:14][n:15][cH:16][c:17]2[cH:18]1 | CC(C)(C)OC(=O)N1CCC(Oc2cccc3cnccc23)CC1 | c1cc(OC2CCNCC2)c2ccncc2c1 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(OC2CCNCC2)c2ccncc2c1 | 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] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 45 (164 mg) and 10% hydrogen chloride/methanol solution (5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with met... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(Oc2cccc3cnccc23)CC1>>c1cc(OC2CCNCC2)c2ccncc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d468fd2f35634bbfb59c0f3c2c17ef5c | CC(C)(C)OC(=O)N1CCC(=O)CC1.CN>>CC(C)(C)OC(=O)N1CCC(CN)CC1 | Cl.CN.C(C)(C)(C)OC(=O)N1CCC(CC1)=O>>NCC1CCN(CC1)C(=O)OC(C)(C)C | O=[C: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.[CH3:12][NH2:13]>>[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][NH2:13])[CH2:14][CH2:15]1 | CC(C)(C)OC(=O)N1CCC(=O)CC1.CN | CC(C)(C)OC(=O)N1CCC(CN)CC1 | null | [Pt]=O | CO | C-C Coupling | OtherReaction | 14bcc3d5cb0dcac5a2469be26468af2477782b3701e5498fcf8d7c85badaa1c1 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | C1CCNCC1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[CH3;D1;+0:7]-[N;D1;H2:8]>>[N;D1;H2:8]-[CH2;D2;+0:7]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1 | 93.9 | [{"value": 93.9, "product": "NCC1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of methylamine hydrochloride (1.01 g, Wako Pure Chemical Industries) and 1-(tert-butoxycarbonyl)-4-oxopiperidine (1.99 g, Aldrich) in methanol (13 ml) was stirred in the presence of platinum oxide (69 mg, Wako Pure Chemical Industries) at room temperature for 3 hours under hydrogen atmosphere of ordinary pre... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | Other | [Pt]=O.CO | null | null | CC(C)(C)OC(=O)N1CCC(=O)CC1.CN>[Pt]=O.CO>CC(C)(C)OC(=O)N1CCC(CN)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c2cdce0bfcd242c092bbc9b6cdab22de | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Br)c23)CC1>>Brc1cncc2cccc(NC3CCNCC3)c12 | BrC1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.Cl.CO>>Cl.BrC1=CN=CC2=CC=CC(=C12)NC1CCNCC1 | CC(C)(C)OC(=O)[N:15]1[CH2:14][CH2:13][CH:12]([NH:11][c:10]2[cH:9][cH:8][cH:7][c:6]3[cH:5][n:4][cH:3][c:2]([Br:1])[c:18]32)[CH2:17][CH2:16]1>>[Br:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([NH:11][CH:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)[c:18]12 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Br)c23)CC1 | Brc1cncc2cccc(NC3CCNCC3)c12 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(NC2CCNCC2)c2ccncc2c1 | 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] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 71 (123 mg) and 10% hydrogen chloride/methanol solution (6 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with met... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2cnccc2c1.C1CCNCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Br)c23)CC1>>Brc1cncc2cccc(NC3CCNCC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-da4afad36c4f493fbe7676c2dafd28c1 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Br)c23)CC1.[F-]>>CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(F)c23)CC1 | BrC1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.[F-].[Cs+]>>FC1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C | Br[c:21]1[cH:20][n:19][cH:18][c:17]2[cH:16][cH:15][cH:14][c:13]([NH:12][CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:25][CH2:24]3)[c:23]21.[F-:22]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([NH:12][c:13]2[cH:14][cH:15][cH:16][c:17]3[cH:18][n:19][cH... | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Br)c23)CC1.[F-] | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(F)c23)CC1 | null | null | CS(=O)C | Functional Group Interconversion | OtherReaction | aa78c0e2316a6dfe08001566d0f24f6ef11c0313c23f6e9a699dc1e464209d61 | 4131cd1655d0ec8ecf7e181a36ab37eb3293d734e38ece0acf0e59405d170401 | c1cc(NC2CCNCC2)c2ccncc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7].[F-;H0;D0:8]>>[F;H0;D1;+0:8]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7] | 23.9 | [{"value": 23.9, "product": "FC1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 150 | CELSIUS | 8 | HOUR | A solution of Intermediate 71 (104 mg) in dimethyl sulfoxide (2 ml) was added with cesium fluoride (284 mg, Wako Pure Chemical Industries) and stirred at 150° C. for 8 hours. The reaction mixture was cooled to room temperature and then filtered through Celite. The residue was added with water (20 ml), extracted with et... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Aromatic halide | c1ccc2cnccc2c1 | c1ccc2cnccc2c1 | C1CC[NH]CC1.c1ccc2cnccc2c1 | Br- | CS(=O)C | 150 | 8 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Br)c23)CC1.[F-]>CS(=O)C>CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(F)c23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c17282f2eff94c059e2a09b237b7e77a | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(F)c23)CC1>>Fc1cncc2cccc(NC3CCNCC3)c12 | FC1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.Cl.CO>>Cl.FC1=CN=CC2=CC=CC(=C12)NC1CCNCC1 | CC(C)(C)OC(=O)[N:16]1[CH2:15][CH2:14][CH:13]([NH:12][c:11]2[cH:10][cH:9][cH:8][c:7]3[cH:6][n:5][cH:4][c:3]([F:2])[c:19]32)[CH2:18][CH2:17]1>>[F:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[c:19]12 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(F)c23)CC1 | Fc1cncc2cccc(NC3CCNCC3)c12 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(NC2CCNCC2)c2ccncc2c1 | 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] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 72 (30.2 mg) and 10% hydrogen chloride/methanol solution (3 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with me... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2cnccc2c1.C1CCNCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(F)c23)CC1>>Fc1cncc2cccc(NC3CCNCC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-daedd6bee30f484fb7b742c746a69337 | CSc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12>>CSc1cncc2cccc(NC3CCNCC3)c12 | CSC1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.Cl.CO>>Cl.CSC1=CN=CC2=CC=CC(=C12)NC1CCNCC1 | CC(C)(C)OC(=O)[N:16]1[CH2:15][CH2:14][CH:13]([NH:12][c:11]2[cH:10][cH:9][cH:8][c:7]3[cH:6][n:5][cH:4][c:3]([S:2][CH3:1])[c:19]32)[CH2:18][CH2:17]1>>[CH3:1][S:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[c:19]12 | CSc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 | CSc1cncc2cccc(NC3CCNCC3)c12 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(NC2CCNCC2)c2ccncc2c1 | 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] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 74 (214 mg) and 10% hydrogen chloride/methanol solution (5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with met... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2cnccc2c1.C1CCNCC1 | HO- | null | null | null | CSc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12>>CSc1cncc2cccc(NC3CCNCC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2e9115487cd940a38efae8fd5e24df8a | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Br)c23)CC1.Cc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1>>Cc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 | BrC1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.C[Sn](C)(C)C.C(C)(C)(C)C1=C(C(=CC(=C1)C)C(C)(C)C)O>>CC1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C | Br[c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([NH:11][CH:12]3[CH2:13][CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][CH2:24]3)[c:25]12.CC(C)(C)c1cc([CH3:1])cc(C(C)(C)C)c1O>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([NH:11][CH:12]3[CH2:13][CH2:14][N:15]([C:16]... | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Br)c23)CC1.Cc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1 | Cc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | OtherReaction | 97910f5eb556ac900e7b376fa52c06a18456b9862405e525f85d744e9ca92a9d | 65063d04424efe73d77012373052a6459d6dbe14093a552d44836b582c9a5c53 | c1cc(NC2CCNCC2)c2ccncc2c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7].C-C(-C)(-C)-c1:c:c(-[CH3;D1;+0:8]):c:c(-C(-C)(-C)-C):c:1-O>>[CH3;D1;+0:8]-[c;H0;D3;+0:1]1:[c:2]:[#7;a:3]:[c:4]:[c:5]:[c:6]:1:[c:7] | null | [] | 150 | CELSIUS | 48 | HOUR | A solution of Intermediate 71 (313 mg) in toluene (6 ml) was added with tetrakis(triphenylphosphine)palladium(0) (17.9 mg, Aldrich), tetramethyltin (165 μl, Kanto Chemicals) and 2,6-di-tert-butyl-4-methylphenol (several pellets, Tokyo Kasei Kogyo) and stirred in a sealed tube at 150° C. for 48 hours. The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | null | c1ccc2cnccc2c1.c1ccccc1 | c1ccc2cnccc2c1 | c1ccc2cnccc2c1.C1CC[NH]CC1 | HBr | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C | 150 | 48 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(Br)c23)CC1.Cc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C>Cc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b671ee9a0ae746f496e932de4e8b9c07 | Cc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12>>Cc1cncc2cccc(NC3CCNCC3)c12 | CC1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.Cl.CO>>Cl.CC1=CN=CC2=CC=CC(=C12)NC1CCNCC1 | CC(C)(C)OC(=O)[N:15]1[CH2:14][CH2:13][CH:12]([NH:11][c:10]2[cH:9][cH:8][cH:7][c:6]3[cH:5][n:4][cH:3][c:2]([CH3:1])[c:18]32)[CH2:17][CH2:16]1>>[CH3:1][c:2]1[cH:3][n:4][cH:5][c:6]2[cH:7][cH:8][cH:9][c:10]([NH:11][CH:12]3[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)[c:18]12 | Cc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 | Cc1cncc2cccc(NC3CCNCC3)c12 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(NC2CCNCC2)c2ccncc2c1 | 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] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 75 (90.7 mg) and 10% hydrogen chloride/methanol solution (2 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with me... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2cnccc2c1.C1CCNCC1 | HO- | null | null | null | Cc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12>>Cc1cncc2cccc(NC3CCNCC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-50d3985a248b4699b78cd3135ee56178 | CC(C)(C)OC(=O)NC1CCC(Nc2cccc3cncc(Br)c23)CC1>>NC1CCC(Nc2cccc3cncc(Br)c23)CC1 | C(C)(C)(C)OC(=O)NC1CCC(CC1)NC1=C2C(=CN=CC2=CC=C1)Br.Cl.CO>>Cl.BrC1=CN=CC2=CC=CC(=C12)NC1CCC(CC1)N | CC(C)(C)OC(=O)[NH:2][CH:3]1[CH2:4][CH2:5][CH:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][n:14][cH:15][c:16]([Br:17])[c:18]23)[CH2:19][CH2:20]1>>[NH2:2][CH:3]1[CH2:4][CH2:5][CH:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][n:14][cH:15][c:16]([Br:17])[c:18]23)[CH2:19][CH2:20]1 | CC(C)(C)OC(=O)NC1CCC(Nc2cccc3cncc(Br)c23)CC1 | NC1CCC(Nc2cccc3cncc(Br)c23)CC1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(NC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 76 (124 mg) and 10% hydrogen chloride/methanol solution (3 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with met... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCCCC1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NC1CCC(Nc2cccc3cncc(Br)c23)CC1>>NC1CCC(Nc2cccc3cncc(Br)c23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-111ff57987e04934a9f32b32aff15edd | CC(C)(C)OC(=O)NC1CCC(Nc2cccc3cncc(F)c23)CC1>>NC1CCC(Nc2cccc3cncc(F)c23)CC1 | C(C)(C)(C)OC(=O)NC1CCC(CC1)NC1=C2C(=CN=CC2=CC=C1)F.Cl.CO>>Cl.FC1=CN=CC2=CC=CC(=C12)NC1CCC(CC1)N | CC(C)(C)OC(=O)[NH:2][CH:3]1[CH2:4][CH2:5][CH:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][n:14][cH:15][c:16]([F:17])[c:18]23)[CH2:19][CH2:20]1>>[NH2:2][CH:3]1[CH2:4][CH2:5][CH:6]([NH:7][c:8]2[cH:9][cH:10][cH:11][c:12]3[cH:13][n:14][cH:15][c:16]([F:17])[c:18]23)[CH2:19][CH2:20]1 | CC(C)(C)OC(=O)NC1CCC(Nc2cccc3cncc(F)c23)CC1 | NC1CCC(Nc2cccc3cncc(F)c23)CC1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(NC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 77 (90.8 mg) and 10% hydrogen chloride/methanol solution (2 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with me... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | C1CCCCC1.c1ccc2cnccc2c1 | HO- | null | null | null | CC(C)(C)OC(=O)NC1CCC(Nc2cccc3cncc(F)c23)CC1>>NC1CCC(Nc2cccc3cncc(F)c23)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b59867340aaa44959c4661c4e65259c3 | CSc1cncc2cccc(NC3CCC(NC(=O)OC(C)(C)C)CC3)c12>>CSc1cncc2cccc(NC3CCC(N)CC3)c12 | C(C)(C)(C)OC(=O)NC1CCC(CC1)NC1=C2C(=CN=CC2=CC=C1)SC.Cl.CO>>Cl.CSC1=CN=CC2=CC=CC(=C12)NC1CCC(CC1)N | CC(C)(C)OC(=O)[NH:17][CH:16]1[CH2:15][CH2:14][CH:13]([NH:12][c:11]2[cH:10][cH:9][cH:8][c:7]3[cH:6][n:5][cH:4][c:3]([S:2][CH3:1])[c:20]32)[CH2:19][CH2:18]1>>[CH3:1][S:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15][CH:16]([NH2:17])[CH2:18][CH2:19]3)[c:20]12 | CSc1cncc2cccc(NC3CCC(NC(=O)OC(C)(C)C)CC3)c12 | CSc1cncc2cccc(NC3CCC(N)CC3)c12 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1cc(NC2CCCCC2)c2ccncc2c1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 78 (341 mg) and 10% hydrogen chloride/methanol solution (5 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with met... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccc2cnccc2c1.C1CCCCC1 | HO- | null | null | null | CSc1cncc2cccc(NC3CCC(NC(=O)OC(C)(C)C)CC3)c12>>CSc1cncc2cccc(NC3CCC(N)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-43fad62811f54559b279903164b86c04 | CSc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12.OO>>CS(=O)c1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 | CSC1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.C(C)(=O)O.OO>>CS(=O)C1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C | [CH3:1][S:2][c:4]1[cH:5][n:6][cH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([NH:13][CH:14]3[CH2:15][CH2:16][N:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:25][CH2:26]3)[c:27]12.O[OH:3]>>[CH3:1][S:2](=[O:3])[c:4]1[cH:5][n:6][cH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([NH:13][CH:14]3[CH2:15][CH2:16][N:17]([C:18](=... | CSc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12.OO | CS(=O)c1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 | null | null | C(C)(=O)OCC | Oxidation | Sulfanyl to sulfinyl_H2O2 | 3f94fa67dce0f9d1622f25c2f6b679e0a2528e6d5c5559b15aed37456745a4b5 | 099322fb111e24ec324e6fad75d493a762ca0cd5af0df8c6f3bfd25c910b45a8 | c1cc(NC2CCNCC2)c2ccncc2c1 | O-[OH;D1;+0:1].[C;D1;H3:2]-[S;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8]>>[C;D1;H3:2]-[S;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4](:[c:5]):[c:6]:[#7;a:7]:[c:8] | null | [] | null | null | 17 | HOUR | Intermediate 74 (746 mg) obtained in Example 105, Step B was added with acetic acid (1.5 ml) and 30% aqueous hydrogen peroxide (2 ml) and stirred at room temperature for 17 hours. The reaction mixture was added with ethyl acetate (50 ml) and washed three times with saturated aqueous sodium hydrogencarbonate (25 ml for ... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide.Monosulfide | Sulfoxide | null | null | c1ccc2cnccc2c1.C1CC[NH]CC1 | HO- | C(C)(=O)OCC | null | 17 | CSc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12.OO>C(C)(=O)OCC>CS(=O)c1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6fb0dd10e1f9415d9ffb3aac8812cd63 | CS(=O)c1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12>>CS(=O)c1cncc2cccc(NC3CCNCC3)c12 | CS(=O)C1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.Cl.CO>>Cl.CS(=O)C1=CN=CC2=CC=CC(=C12)NC1CCNCC1 | CC(C)(C)OC(=O)[N:17]1[CH2:16][CH2:15][CH:14]([NH:13][c:12]2[cH:11][cH:10][cH:9][c:8]3[cH:7][n:6][cH:5][c:4]([S:2]([CH3:1])=[O:3])[c:20]32)[CH2:19][CH2:18]1>>[CH3:1][S:2](=[O:3])[c:4]1[cH:5][n:6][cH:7][c:8]2[cH:9][cH:10][cH:11][c:12]([NH:13][CH:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]3)[c:20]12 | CS(=O)c1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 | CS(=O)c1cncc2cccc(NC3CCNCC3)c12 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(NC2CCNCC2)c2ccncc2c1 | 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] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 79 (138 mg) and 10% hydrogen chloride/methanol solution (3 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with met... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2cnccc2c1.C1CCNCC1 | HO- | null | null | null | CS(=O)c1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12>>CS(=O)c1cncc2cccc(NC3CCNCC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5f8fc3e5b08c415e8eb79577e5b04040 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(S(C)(=O)=O)c23)CC1>>CS(=O)(=O)c1cncc2cccc(NC3CCNCC3)c12 | CS(=O)(=O)C1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.Cl.CO>>Cl.CS(=O)(=O)C1=CN=CC2=CC=CC(=C12)NC1CCNCC1 | CC(C)(C)OC(=O)[N:18]1[CH2:17][CH2:16][CH:15]([NH:14][c:13]2[cH:12][cH:11][cH:10][c:9]3[cH:8][n:7][cH:6][c:5]([S:2]([CH3:1])(=[O:3])=[O:4])[c:21]32)[CH2:20][CH2:19]1>>[CH3:1][S:2](=[O:3])(=[O:4])[c:5]1[cH:6][n:7][cH:8][c:9]2[cH:10][cH:11][cH:12][c:13]([NH:14][CH:15]3[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]3)[c:21]12 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(S(C)(=O)=O)c23)CC1 | CS(=O)(=O)c1cncc2cccc(NC3CCNCC3)c12 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(NC2CCNCC2)c2ccncc2c1 | 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] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 80 (40.9 mg) and 10% hydrogen chloride/methanol solution (1 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with me... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2cnccc2c1.C1CCNCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(Nc2cccc3cncc(S(C)(=O)=O)c23)CC1>>CS(=O)(=O)c1cncc2cccc(NC3CCNCC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dd7fd85d74ac4d629c9b080664ed5570 | C=Cc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12>>C=Cc1cncc2cccc(NC3CCNCC3)c12 | C(=C)C1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.Cl.CO>>Cl.C(=C)C1=CN=CC2=CC=CC(=C12)NC1CCNCC1 | CC(C)(C)OC(=O)[N:16]1[CH2:15][CH2:14][CH:13]([NH:12][c:11]2[cH:10][cH:9][cH:8][c:7]3[cH:6][n:5][cH:4][c:3]([CH:2]=[CH2:1])[c:19]32)[CH2:18][CH2:17]1>>[CH2:1]=[CH:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[c:19]12 | C=Cc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 | C=Cc1cncc2cccc(NC3CCNCC3)c12 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(NC2CCNCC2)c2ccncc2c1 | 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] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 81 (46.6 mg) and 10% hydrogen chloride/methanol solution (2 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with me... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2cnccc2c1.C1CCNCC1 | HO- | null | null | null | C=Cc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12>>C=Cc1cncc2cccc(NC3CCNCC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-33f191967e254d3f863ca6e7e74696a6 | C=Cc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12>>CCc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 | C(=C)C1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C>>C(C)C1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C | [CH2:1]=[CH:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH2:25]3)[c:26]12>>[CH3:1][CH2:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15][N:16]([C:17](=[O:18])[O:19][... | C=Cc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 | CCc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 | null | [C].[Pd] | CO | Reduction | Hydrogenation (double to single) | 8276b4fb5ddc7d15dec6d92474e91e2dbb2fb8b81e5b5720762e5d89cb27aa69 | 1ccae9f2e86499601fc3421041ff4588c8e6fd53048e86c3b6ed12ae873609c0 | c1cc(NC2CCNCC2)c2ccncc2c1 | [CH2;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[CH3;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 90.5 | [{"value": 90.5, "product": "C(C)C1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution (2 ml) of Intermediate 81 (103 mg) in methanol was vigorously stirred in the presence of 10% palladium carbon catalyst (16.5 mg) at room temperature under hydrogen atmosphere of ordinary pressure. The reaction mixture was filtered through Celite, and the solvent was evaporated under reduced pressure. The res... | 10.6084/m9.figshare.5104873.v1 | null | Vinyl | null | null | null | c1ccc2cnccc2c1.C1CC[NH]CC1 | null | [C].[Pd].CO | null | null | C=Cc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12>[C].[Pd].CO>CCc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-749ac926d34d4575ae04f26fcd6095f9 | CCc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12>>CCc1cncc2cccc(NC3CCNCC3)c12 | C(C)C1=CN=CC2=CC=CC(=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.Cl.CO>>Cl.C(C)C1=CN=CC2=CC=CC(=C12)NC1CCNCC1 | CC(C)(C)OC(=O)[N:16]1[CH2:15][CH2:14][CH:13]([NH:12][c:11]2[cH:10][cH:9][cH:8][c:7]3[cH:6][n:5][cH:4][c:3]([CH2:2][CH3:1])[c:19]32)[CH2:18][CH2:17]1>>[CH3:1][CH2:2][c:3]1[cH:4][n:5][cH:6][c:7]2[cH:8][cH:9][cH:10][c:11]([NH:12][CH:13]3[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[c:19]12 | CCc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12 | CCc1cncc2cccc(NC3CCNCC3)c12 | null | null | null | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(NC2CCNCC2)c2ccncc2c1 | 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] | null | [] | null | null | null | null | According to the method of Example 1, Step C, deprotection was performed (50° C., 2 hours) by using Intermediate 82 (93.7 mg) and 10% hydrogen chloride/methanol solution (2 ml). The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The residue was added with me... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccc2cnccc2c1.C1CCNCC1 | HO- | null | null | null | CCc1cncc2cccc(NC3CCN(C(=O)OC(C)(C)C)CC3)c12>>CCc1cncc2cccc(NC3CCNCC3)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c2c568e79a76424c86ebc38f97226234 | O=[N+]([O-])c1cccc2c(Cl)nccc12>>Nc1cccc2c(Cl)nccc12 | O.O.[Sn](Cl)Cl.ClC1=NC=CC2=C(C=CC=C12)[N+](=O)[O-]>>ClC1=NC=CC2=C(C=CC=C12)N | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]([Cl:8])[n:9][cH:10][cH:11][c:12]12>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]2[c:7]([Cl:8])[n:9][cH:10][cH:11][c:12]12 | O=[N+]([O-])c1cccc2c(Cl)nccc12 | Nc1cccc2c(Cl)nccc12 | null | null | C(C)(=O)OCC | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc2cnccc2c1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 70 | CELSIUS | null | null | A solution (40 ml) of 1-chloro-5-nitroisoquinoline (2.23 g, synthesized according to the method described in J. Med. Chem. 45, 3, 740 (2002)) in ethyl acetate was added with tin(II) chloride dihydrate (12.39 g, Wako Pure Chemical Industries) at room temperature and stirred with heating at 70° C. for 1 hour. The reactio... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccc2cnccc2c1 | Other | C(C)(=O)OCC | 70 | null | O=[N+]([O-])c1cccc2c(Cl)nccc12>C(C)(=O)OCC>Nc1cccc2c(Cl)nccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c7ab94fd6f5a4dc4b97d834fc0e5f2b3 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3c(Cl)nccc23)CC1>>Clc1nccc2c(NC3CCNCC3)cccc12 | ClC1=NC=CC2=C(C=CC=C12)NC1CCN(CC1)C(=O)OC(C)(C)C.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.ClC1=NC=CC2=C(C=CC=C12)NC1CCNCC1 | CC(C)(C)OC(=O)[N:12]1[CH2:11][CH2:10][CH:9]([NH:8][c:7]2[c:6]3[cH:5][cH:4][n:3][c:2]([Cl:1])[c:18]3[cH:17][cH:16][cH:15]2)[CH2:14][CH2:13]1>>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6]2[c:7]([NH:8][CH:9]3[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]3)[cH:15][cH:16][cH:17][c:18]12 | CC(C)(C)OC(=O)N1CCC(Nc2cccc3c(Cl)nccc23)CC1 | Clc1nccc2c(NC3CCNCC3)cccc12 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1cc(NC2CCNCC2)c2ccncc2c1 | 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] | null | [] | null | null | null | null | Deprotection was performed (room temperature, 2 hours) by using Intermediate 84 (81.9 mg) and a mixed solution of trifluoroacetic acid and methylene chloride (1:1, 2 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (2 ml) and diethyl ether (6 ml). The deposited precipitate... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | C1CCNCC1.c1ccc2cnccc2c1 | HO- | C(Cl)Cl | null | null | CC(C)(C)OC(=O)N1CCC(Nc2cccc3c(Cl)nccc23)CC1>C(Cl)Cl>Clc1nccc2c(NC3CCNCC3)cccc12 |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.