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-e09d80b009c94883976bbcd98164aff7 | CC(=O)Cl.Nc1cc(Cl)nc(N)n1.O=Cc1ccco1.[C-]#[N+]CC(=O)OC>>COC(=O)CNc1c(-c2ccco2)[n+](C(C)=O)c2nc(Cl)cc(N)n12.[Cl-] | C(C)(=O)Cl.NC1=NC(=CC(=N1)Cl)N.COC(C[N+]#[C-])=O.C(C1=CC=CO1)=O>>[Cl-].C(C)(=O)[N+]=1C(=C(N2C1N=C(C=C2N)Cl)NCC(=O)OC)C=2OC=CC2 | [C:15]([CH3:16])(=[O:17])[Cl:26].[NH2:14][c:18]1[n:19][c:20]([Cl:21])[cH:22][c:23]([NH2:24])[n:25]1.O=[CH:8][c:9]1[cH:10][cH:11][cH:12][o:13]1.[CH3:1][O:2][C:3](=[O:4])[CH2:5][N+:6]#[C-:7]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][NH:6][c:7]1[c:8](-[c:9]2[cH:10][cH:11][cH:12][o:13]2)[n+:14]([C:15]([CH3:16])=[O:17])[c:18]2[n:19... | CC(=O)Cl.Nc1cc(Cl)nc(N)n1.O=Cc1ccco1.[C-]#[N+]CC(=O)OC | COC(=O)CNc1c(-c2ccco2)[n+](C(C)=O)c2nc(Cl)cc(N)n12.[Cl-] | null | null | Cl(=O)(=O)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 9e150fa808eb5b10bc5a9294d590ffd0dd5c709f43db6f92bdb4dc6915e5be79 | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1coc(-c2cn3cccnc3[nH+]2)c1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2]1:[#8;a:3]:[c:4]:[c:5]:[c:6]:1.[C-;H0;D1:7]#[N+;H0;D2:8]-[C:9]-[C:10](=[O;D1;H0:11])-[#8:12]-[C;D1;H3:13].[C;D1;H3:14]-[C;H0;D3;+0:15](-[Cl;H0;D1;+0:16])=[O;D1;H0:17].[N;D1;H2:18]-[c:19]1:[c:20]:[c:21]:[#7;a:22]:[c:23](-[NH2;D1;+0:24]):[n;H0;D2;+0:25]:1>>[C;D1;H3:14]-[C;H0;D3;+0:15](=[O;D1;... | null | [] | null | null | null | null | Example 27 was carried out in accordance with the general directions for synthesis in process step a) from 1.0 ml (0.1 mmol) 2,6-diamino-4-chloro-pyrimidine (0.1 M, DCM), 0.575 ml (0.115 mmol) isocyanoacetic acid methyl ester solution (0.2 M, DCM), 0.500 ml (0.15 mmol) furfural solution (0.3 M, DCM) and 10 μl perchlori... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1cncnc1 | C1=CN2C=C[NH+]=C2N=C1 | c1ccoc1.C1=CN2C=C[NH+]=C2N=C1 | HO- | Cl(=O)(=O)(=O)O | null | null | CC(=O)Cl.Nc1cc(Cl)nc(N)n1.O=Cc1ccco1.[C-]#[N+]CC(=O)OC>Cl(=O)(=O)(=O)O>COC(=O)CNc1c(-c2ccco2)[n+](C(C)=O)c2nc(Cl)cc(N)n12.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e4c706d265db46289094206a40eff50f | CC(=O)Cl.Cc1ccc(N)nc1.O=Cc1ccco1.[C-]#[N+]C1CCCCC1.[O-][Cl+3]([O-])([O-])O>>CC(=O)[n+]1c(-c2ccco2)c(NC2CCCCC2)n2ccccc21.Cl.[Cl-] | CC=1C=CC(=NC1)N.C(C)(=O)Cl.O1C(=CC=C1)C=O.C1(CCCCC1)[N+]#[C-].Cl(=O)(=O)(=O)O>>Cl.[Cl-].C(C)(=O)[N+]=1C(=C(N2C1C=CC=C2)NC2CCCCC2)C=2OC=CC2 | [CH3:1][C:2](=[O:3])[Cl:26].C[c:21]1[cH:20][n:19][c:24]([NH2:4])[cH:23][cH:22]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][o:10]1.[C-:11]#[N+:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1.[O-][Cl+3:25]([O-])([O-])O>>[CH3:1][C:2](=[O:3])[n+:4]1[c:5](-[c:6]2[cH:7][cH:8][cH:9][o:10]2)[c:11]([NH:12][CH:13]2[CH2:14][CH2:15][CH... | CC(=O)Cl.Cc1ccc(N)nc1.O=Cc1ccco1.[C-]#[N+]C1CCCCC1.[O-][Cl+3]([O-])([O-])O | CC(=O)[n+]1c(-c2ccco2)c(NC2CCCCC2)n2ccccc21.Cl.[Cl-] | null | null | CO.O.C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | 8bbf2fc70e5391fc03c95923ce0f6f98f87422fab0662577c39d52af89325f3c | fc55df602c13baf8406061a2210551f8c24e5a088cc079d1f844b71d9c155ccd | c1coc(-c2[nH+]c3ccccn3c2NC2CCCCC2)c1 | C-[c;H0;D3;+0:1]1:[c:2]:[n;H0;D2;+0:3]:[c:4](-[NH2;D1;+0:5]):[c:6]:[c:7]:1.O-[Cl+3;H0;D4:8](-[O-])(-[O-])-[O-].O=[CH;D2;+0:9]-[c;H0;D3;+0:10]1:[#8;a:11]:[c:12]:[c:13]:[c:14]:1.[C-;H0;D1:15]#[N+;H0;D2:16]-[C:17](-[C:18])-[C:19].[C;D1;H3:20]-[C;H0;D3;+0:21](-[Cl;H0;D1;+0:22])=[O;D1;H0:23]>>[C:18]-[C:17](-[NH;D2;+0:16]-[c... | null | [] | null | null | 22 | HOUR | 655 mg (6.1 mmol) 5-methyl-2-aminopyridin were placed in 12 ml methanol, and 874 mg (0.75 ml; 9.1 mmol) furan-2-carbaldehyde, 768 mg (0.86 ml; 7.0 mmol) cyclohexylisonitrile and 0.59 ml aqueous perchloric acid (20 m %) were then added and stirred at ambient temperature for 22 hours. 50 ml water and 40 ml DCM were added... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aldehyde.Isocyanide.Primary amine | Secondary amine | c1ccncc1 | C1=CC2=[NH+]C=CN2C=C1 | c1ccoc1.C1CCCCC1.C1=CC2=[NH+]C=CN2C=C1 | HO- | CO.O.C(Cl)Cl | null | 22 | CC(=O)Cl.Cc1ccc(N)nc1.O=Cc1ccco1.[C-]#[N+]C1CCCCC1.[O-][Cl+3]([O-])([O-])O>CO.O.C(Cl)Cl>CC(=O)[n+]1c(-c2ccco2)c(NC2CCCCC2)n2ccccc21.Cl.[Cl-] |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4825907718a34102b76de664069c39ba | CC(=O)OC(C)=O.CCC(N)C(=O)O>>CCC(NC(C)=O)C(=O)O | NC(C(=O)O)CC.C(C)(=O)OC(C)=O>>C(C)(=O)NC(C(=O)O)CC | CC(=O)O[C:5]([CH3:6])=[O:7].[CH3:1][CH2:2][CH:3]([NH2:4])[C:8](=[O:9])[OH:10]>>[CH3:1][CH2:2][CH:3]([NH:4][C:5]([CH3:6])=[O:7])[C:8](=[O:9])[OH:10] | CC(=O)OC(C)=O.CCC(N)C(=O)O | CCC(NC(C)=O)C(=O)O | null | null | C(C)(=O)O | Acylation | Aminolysis of esters | 87d35e51b477fc9a658a6f307eb56d84c8879182772c9dd3a42ec0d584fd2684 | 627cbc0550c9f51ad0105d9fcf46677e8c93bed87ee95bfe69292a82550c95b7 | null | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[C:4]-[C:5](-[NH2;D1;+0:6])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9]>>[C:4]-[C:5](-[NH;D2;+0:6]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])-[C:7](=[O;D1;H0:8])-[O;D1;H1:9] | null | [] | 100 | CELSIUS | 2 | HOUR | 163 g (1.58 mol) 2-aminobutanoic acid are dissolved in acetic acid, and 242 g (2.37 mol) acetic anhydride are added dropwise. The mixture is stirred for 2 h at 100° C. until completion of reaction, then the solution evaporated to dryness in vacuo. The solid residue is suspended in ethyl acetate, filtered and washed wit... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Primary amine | Secondary amide | null | null | null | HO- | C(C)(=O)O | 100 | 2 | CC(=O)OC(C)=O.CCC(N)C(=O)O>C(C)(=O)O>CCC(NC(C)=O)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-104f1562f4d446dfad9da36770411e4b | CCC(NC(C)=O)C(=O)O.CCOC(=O)C(=O)Cl>>CCOC(=O)C(=O)C(CC)NC(C)=O | ClC(C(=O)OCC)=O.C(C)(=O)NC(C(=O)O)CC.N1=CC=CC=C1>>C(C)(=O)NC(C(C(=O)OCC)=O)CC | O=C(O)[CH:8]([CH2:9][CH3:10])[NH:11][C:12]([CH3:13])=[O:14].Cl[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[CH:8]([CH2:9][CH3:10])[NH:11][C:12]([CH3:13])=[O:14] | CCC(NC(C)=O)C(=O)O.CCOC(=O)C(=O)Cl | CCOC(=O)C(=O)C(CC)NC(C)=O | null | null | O1CCCC1 | C-C Coupling | Ketonization by decarboxylation of acid halides | aaebaa0d813a71dc889ae147df75d12dcb32900152f1a5154d5b3ca46552ea1b | 3f61ba26fe9791436c27b93d0c669474775a60e3446708a267a9de08824bde1e | null | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[#8:5]-[C:6].O-C(=O)-[CH;D3;+0:7](-[#7:8]-[C:9](-[C;D1;H3:10])=[O;D1;H0:11])-[C:12]-[C;D1;H3:13]>>[C:6]-[#8:5]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH;D3;+0:7](-[#7:8]-[C:9](-[C;D1;H3:10])=[O;D1;H0:11])-[C:12]-[C;D1;H3:13] | null | [] | null | null | null | null | 9.2 g (63.4 mmol) 2-(acetylamino)butanoic acid are suspended in 120 ml tetrahydro-furane and heated to reflux together with 15.0 g (190 mmol) pyridine and a bit of N,N-dimethylaminopyridine. While heating at reflux, 17.3 g (127 mmol) ethyl chloro(oxo)acetate are added dropwise. The reaction mixture is heated at reflux ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Ester | Ketone | null | null | null | HCl | O1CCCC1 | null | null | CCC(NC(C)=O)C(=O)O.CCOC(=O)C(=O)Cl>O1CCCC1>CCOC(=O)C(=O)C(CC)NC(C)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-adc6fca9416e4444a84e843c2bdf93a5 | N#Cc1cccc(Br)c1.[Cl-].[NH4+]>>Cl.N=C(N)c1cccc(Br)c1 | BrC=1C=C(C#N)C=CC1.[Cl-].[NH4+].C[Al](C)C.CO>>Cl.BrC=1C=C(C=CC1)C(N)=N | [N:2]#[C:3][c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[cH:11]1.[Cl-:1].[NH4+:4]>>[ClH:1].[NH:2]=[C:3]([NH2:4])[c:5]1[cH:6][cH:7][cH:8][c:9]([Br:10])[cH:11]1 | N#Cc1cccc(Br)c1.[Cl-].[NH4+] | Cl.N=C(N)c1cccc(Br)c1 | null | null | CCCCCC.C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 3b047a13c16a607c445b1c419e256808e8c9a0097d8fb9efd4e7970deb782b70 | 2882e57127fc469aa16ca9a2fd53388b6d97c74c76c010e6eb01be5726f46aa5 | c1ccccc1 | [Cl-;H0;D0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4](:[c:5]):[c:6].[NH4+;D0:7]>>[ClH;D0;+0:1].[NH2;D1;+0:7]-[C;H0;D3;+0:3](=[NH;D1;+0:2])-[c:4](:[c:5]):[c:6] | null | [] | 0 | CELSIUS | null | null | 1.18 g (22 mmol, 2 equiv.) ammonium chloride are suspended in 40 ml of dry toluene under an argon atmosphere, and the mixture is cooled to 0° C. 11 ml (22 mmol, 2 equiv.) of a 2M solution of trimethylaluminium in hexane are added dropwise, and the reaction mixture is stirred at room temperature until no more evolution ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1 | null | CCCCCC.C1(=CC=CC=C1)C | 0 | null | N#Cc1cccc(Br)c1.[Cl-].[NH4+]>CCCCCC.C1(=CC=CC=C1)C>Cl.N=C(N)c1cccc(Br)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-df7e8f4754984965badaea04cfade0f5 | N#Cc1cccc2ccccc12.[Cl-].[NH4+]>>Cl.N=C(N)c1cccc2ccccc12 | C(#N)C1=CC=CC2=CC=CC=C12.[Cl-].[NH4+].C[Al](C)C>>Cl.C1(=CC=CC2=CC=CC=C12)C(N)=N | [N:2]#[C:3][c:5]1[cH:6][cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12.[Cl-:1].[NH4+:4]>>[ClH:1].[NH:2]=[C:3]([NH2:4])[c:5]1[cH:6][cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12 | N#Cc1cccc2ccccc12.[Cl-].[NH4+] | Cl.N=C(N)c1cccc2ccccc12 | null | null | CCCCCC.C(Cl)Cl.C1(=CC=CC=C1)C | Functional Group Interconversion | OtherReaction | 3b047a13c16a607c445b1c419e256808e8c9a0097d8fb9efd4e7970deb782b70 | 2882e57127fc469aa16ca9a2fd53388b6d97c74c76c010e6eb01be5726f46aa5 | c1ccc2ccccc2c1 | [Cl-;H0;D0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4](:[c:5]):[c:6].[NH4+;D0:7]>>[ClH;D0;+0:1].[NH2;D1;+0:7]-[C;H0;D3;+0:3](=[NH;D1;+0:2])-[c:4](:[c:5]):[c:6] | null | [] | 0 | CELSIUS | null | null | 14 g (261 mmol, 2 equiv.) ammonium chloride are suspended in 150 ml of dry toluene under an argon athmosphere, and the mixture is cooled to 0° C. 130 ml (260 mmol, 2 equiv.) of a 2M solution of trimethylaluminium in hexane are added dropwise, and the reaction mixture is stirred at room temperature until no more evoluti... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccc2ccccc2c1 | null | CCCCCC.C(Cl)Cl.C1(=CC=CC=C1)C | 0 | null | N#Cc1cccc2ccccc12.[Cl-].[NH4+]>CCCCCC.C(Cl)Cl.C1(=CC=CC=C1)C>Cl.N=C(N)c1cccc2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-724263f0c615489ea3039922097a8ea6 | CCOC(=O)C(=O)C(CC)NC(C)=O.N=C(N)c1cccc(Br)c1.NN>>CCC(NC(C)=O)c1nnc(-c2cccc(Br)c2)[nH]c1=O | Cl.BrC=1C=C(C=CC1)C(N)=N.C(C)(=O)NC(C(C(=O)OCC)=O)CC.O.NN>>BrC=1C=C(C=CC1)C1=NN=C(C(N1)=O)C(CC)NC(C)=O | CCO[C:20]([C:8](=O)[CH:3]([CH2:2][CH3:1])[NH:4][C:5]([CH3:6])=[O:7])=[O:21].N=[C:11]([c:12]1[cH:13][cH:14][cH:15][c:16]([Br:17])[cH:18]1)[NH2:19].[NH2:9][NH2:10]>>[CH3:1][CH2:2][CH:3]([NH:4][C:5]([CH3:6])=[O:7])[c:8]1[n:9][n:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][c:16]([Br:17])[cH:18]2)[nH:19][c:20]1=[O:21] | CCOC(=O)C(=O)C(CC)NC(C)=O.N=C(N)c1cccc(Br)c1.NN | CCC(NC(C)=O)c1nnc(-c2cccc(Br)c2)[nH]c1=O | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | e7bab37df0829099558b3ea1b1d6c14ca29d111a0fe7c4e70294ed15a1035365 | b9a6c12d0e1239b0cb412542e52dae4bfecd4fc5a7cf6f6405348266ba7aff2e | O=c1cnnc(-c2ccccc2)[nH]1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=O)-[C:4](-[C:5])-[#7:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9].N=[C;H0;D3;+0:10](-[NH2;D1;+0:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15]:[c:16].[NH2;D1;+0:17]-[NH2;D1;+0:18]>>[C:5]-[C:4](-[#7:6]-[C:7](-[C;D1;H3:8])=[O;D1;H0:9])-[c;H0;D3;+0:3]1:[n;H0;D2;+0:18]:[n;H0;D2;+0:17]:... | null | [] | null | null | 1 | HOUR | 2.02 (8.6 mmol, 1 equiv.) 3-bromobenzenecarboximidamide hydrochloride are suspended in 50 ml of ethanol and 1.47 g (10.2 mmol, 1.2 equiv.) hydrazine hydrate are added. After stirring at room temperature for 1 hour, 2.59 g (13 mmol, 1.5 equiv) of the compound of Example 2A, dissolved in 10 ml of ethanol, are added. The ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester.Primary amine | null | null | c1cnncn1 | c1cnncn1.c1ccccc1 | HO- | C(C)O | null | 1 | CCOC(=O)C(=O)C(CC)NC(C)=O.N=C(N)c1cccc(Br)c1.NN>C(C)O>CCC(NC(C)=O)c1nnc(-c2cccc(Br)c2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-00d5b1f294a447d5b9529db33c3cae5a | CCC(N)c1nnc(-c2ccc(Br)cc2)[nH]c1=O.O=C(Cl)C1CCCC1>>CCC(NC(=O)C1CCCC1)c1nnc(-c2ccc(Br)cc2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1=CC=C(C=C1)Br)=O.C1(CCCC1)C(=O)Cl>>BrC1=CC=C(C=C1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCCC1 | [CH3:1][CH2:2][CH:3]([NH2:4])[c:12]1[n:13][n:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([Br:20])[cH:21][cH:22]2)[nH:23][c:24]1=[O:25].Cl[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[c:12]1[n:13][n:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([... | CCC(N)c1nnc(-c2ccc(Br)cc2)[nH]c1=O.O=C(Cl)C1CCCC1 | CCC(NC(=O)C1CCCC1)c1nnc(-c2ccc(Br)cc2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc(-c2ccccc2)[nH]c1=O)C1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH2;D1;+0:11]):[c:12]:[#7;a:13]>>[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]):[c:12]:[#7;a:13] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 3.35 g (10.8 mmol) 6-(1-aminopropyl)-3-(4-bromophenyl)-1,2,4-triazin-5(4H)-one, 2.16 g (16.3 mmol) cyclopentanecarbonyl chloride and proportionate amounts of the other reagents are used.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCC1.c1cnncn1.c1ccccc1 | HCl | null | null | null | CCC(N)c1nnc(-c2ccc(Br)cc2)[nH]c1=O.O=C(Cl)C1CCCC1>>CCC(NC(=O)C1CCCC1)c1nnc(-c2ccc(Br)cc2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e8a991ceb0764091bbad87e8571af243 | CCC(N)c1nnc(C2CC2)[nH]c1=O.O=C(Cl)C1CCC1>>CCC(NC(=O)C1CCC1)c1nnc(C2CC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CC1)=O.C1(CCC1)C(=O)Cl>>C1(CC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCC1 | [CH3:1][CH2:2][CH:3]([NH2:4])[c:11]1[n:12][n:13][c:14]([CH:15]2[CH2:16][CH2:17]2)[nH:18][c:19]1=[O:20].Cl[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10]1>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10]1)[c:11]1[n:12][n:13][c:14]([CH:15]2[CH2:16][CH2:17]2)[nH:18][c:19]1=[O:20] | CCC(N)c1nnc(C2CC2)[nH]c1=O.O=C(Cl)C1CCC1 | CCC(NC(=O)C1CCC1)c1nnc(C2CC2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc(C2CC2)[nH]c1=O)C1CCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH2;D1;+0:11]):[c:12]:[#7;a:13]>>[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]):[c:12]:[#7;a:13] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 250 mg (1.29 mmol) 6-(1-aminopropyl)-3-cyclopropyl-1,2,4-triazin-5(4H)-one, 150 mg (1.29 mmol) cyclobutanecarbonyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCC1.c1cnncn1.C1CC1 | HCl | null | null | null | CCC(N)c1nnc(C2CC2)[nH]c1=O.O=C(Cl)C1CCC1>>CCC(NC(=O)C1CCC1)c1nnc(C2CC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6913902c0d744d708d3052c48a047039 | CCC(N)c1nnc(C2CC2)[nH]c1=O.O=C(Cl)C1CCCC1>>CCC(NC(=O)C1CCCC1)c1nnc(C2CC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CC1)=O.C1(CCCC1)C(=O)Cl>>C1(CC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCCC1 | [CH3:1][CH2:2][CH:3]([NH2:4])[c:12]1[n:13][n:14][c:15]([CH:16]2[CH2:17][CH2:18]2)[nH:19][c:20]1=[O:21].Cl[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[c:12]1[n:13][n:14][c:15]([CH:16]2[CH2:17][CH2:18]2)[nH:19][c:20]1=[O:21] | CCC(N)c1nnc(C2CC2)[nH]c1=O.O=C(Cl)C1CCCC1 | CCC(NC(=O)C1CCCC1)c1nnc(C2CC2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc(C2CC2)[nH]c1=O)C1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH2;D1;+0:11]):[c:12]:[#7;a:13]>>[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]):[c:12]:[#7;a:13] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 250 mg (1.29 mmol) 6-(1-aminopropyl)-3-cyclopropyl-1,2,4-triazin-5(4H)-one, 170 mg (1.29 mmol) cyclopentanecarbonyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCC1.c1cnncn1.C1CC1 | HCl | null | null | null | CCC(N)c1nnc(C2CC2)[nH]c1=O.O=C(Cl)C1CCCC1>>CCC(NC(=O)C1CCCC1)c1nnc(C2CC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4bcafa10a53542d891597c168d3e248e | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)C1CCC1>>CCC(NC(=O)C1CCC1)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.C1(CCC1)C(=O)Cl>>C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCC1 | [CH3:1][CH2:2][CH:3]([NH2:4])[c:11]1[n:12][n:13][c:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[nH:20][c:21]1=[O:22].Cl[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10]1>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10]1)[c:11]1[n:12][n:13][c:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[nH:20][c:21]1=... | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)C1CCC1 | CCC(NC(=O)C1CCC1)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc(C2CCCC2)[nH]c1=O)C1CCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH2;D1;+0:11]):[c:12]:[#7;a:13]>>[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]):[c:12]:[#7;a:13] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 200 mg (0.90 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 110 mg (0.90 mmol) cyclobutanecarbonyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions: See reac... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCC1.c1cnncn1.C1CCCC1 | HCl | null | null | null | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)C1CCC1>>CCC(NC(=O)C1CCC1)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4759b48bc3994b8d90d39aa5071c2947 | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)C1CCCC1>>CCC(NC(=O)C1CCC1)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.C1(CCCC1)C(=O)Cl>>C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCC1 | [CH3:1][CH2:2][CH:3]([NH2:4])[c:11]1[n:12][n:13][c:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[nH:20][c:21]1=[O:22].Cl[C:5](=[O:6])[CH:7]1[CH2:8]C[CH2:9][CH2:10]1>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10]1)[c:11]1[n:12][n:13][c:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[nH:20][c:21]1... | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)C1CCCC1 | CCC(NC(=O)C1CCC1)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | OtherReaction | 5f6f976eef907a334ca800a7921c607c7f0cea6bc2eafb79320c1f43000961e4 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc(C2CCCC2)[nH]c1=O)C1CCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[CH2;D2;+0:5]-C-[CH2;D2;+0:6]-1.[#7;a:7]:[#7;a:8]:[c:9](-[C:10](-[C:11])-[NH2;D1;+0:12]):[c:13]:[#7;a:14]>>[#7;a:7]:[#7;a:8]:[c:9](-[C:10](-[C:11])-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[CH2;D2;+0:5]-[CH2;D2;+0:6]-1):[c:13]:[#7;a:14] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 200 mg (0.90 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 120 mg (0.90 mmol) cyclopentanecarbonyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | C1CCCC1 | C1CCC1 | C1CCC1.c1cnncn1.C1CCCC1 | HCl | null | null | null | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)C1CCCC1>>CCC(NC(=O)C1CCC1)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b46f015255f1488ebf4026b731b6fb22 | CCC(N)c1nnc(C(C)(C)C)[nH]c1=O.O=C(Cl)C1CCCC1>>CCC(NC(=O)C1CCCC1)c1nnc(C(C)(C)C)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C(C)(C)C)=O.C1(CCCC1)C(=O)Cl>>C(C)(C)(C)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCCC1 | [CH3:1][CH2:2][CH:3]([NH2:4])[c:12]1[n:13][n:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[nH:20][c:21]1=[O:22].Cl[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[c:12]1[n:13][n:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[nH:20][c:21]... | CCC(N)c1nnc(C(C)(C)C)[nH]c1=O.O=C(Cl)C1CCCC1 | CCC(NC(=O)C1CCCC1)c1nnc(C(C)(C)C)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc[nH]c1=O)C1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH2;D1;+0:11]):[c:12]:[#7;a:13]>>[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]):[c:12]:[#7;a:13] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 110 mg (0.50 mmol) 6-(1-aminopropyl)-3-tert-butyl-1,2,4-triazin-5(4H)-one, 70 mg (0.50 mmol) cyclopentanecarbonyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions: See react... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCC1.c1cnncn1 | HCl | null | null | null | CCC(N)c1nnc(C(C)(C)C)[nH]c1=O.O=C(Cl)C1CCCC1>>CCC(NC(=O)C1CCCC1)c1nnc(C(C)(C)C)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fea17c083a1e486d9dd4e00e7e5ed49c | CCC(N)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O.O=C(Cl)C1CCCC1>>CCC(NC(=O)C1CCCC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1=CC(=CC=C1)[N+](=O)[O-])=O.C1(CCCC1)C(=O)Cl>>[N+](=O)([O-])C=1C=C(C=CC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCCC1 | [CH3:1][CH2:2][CH:3]([NH2:4])[c:12]1[n:13][n:14][c:15](-[c:16]2[cH:17][cH:18][cH:19][c:20]([N+:21](=[O:22])[O-:23])[cH:24]2)[nH:25][c:26]1=[O:27].Cl[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[c:12]1[n:13][n:14][c:15](-[c:16]2[cH:17... | CCC(N)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O.O=C(Cl)C1CCCC1 | CCC(NC(=O)C1CCCC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc(-c2ccccc2)[nH]c1=O)C1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH2;D1;+0:11]):[c:12]:[#7;a:13]>>[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]):[c:12]:[#7;a:13] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 3.0 g (10.9 mmol) 6-(1-aminopropyl)-3-(3-nitrophenyl)-1,2,4-triazin-5(4H)-one, 2.2 g (16.3 mmol) cyclopentanecarbonyl chloride and proportionate amounts of the other reagents are used.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCC1.c1cnncn1.c1ccccc1 | HCl | null | null | null | CCC(N)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O.O=C(Cl)C1CCCC1>>CCC(NC(=O)C1CCCC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ac4239c9e35d4f9abbabb31f98870e4d | CCOC(=O)C(=O)C(CC)NC(=O)C1CCCC1.N=C(N)c1ccccc1.NN>>CCC(NC(=O)C1CCCC1)c1nnc(-c2ccccc2)[nH]c1=O | C1(CCCC1)C(=O)NC(C(C(=O)OCC)=O)CC.Cl.C1(=CC=CC=C1)C(N)=N.O.NN>>O=C1NC(=NN=C1C(CC)NC(=O)C1CCCC1)C1=CC=CC=C1 | CCO[C:23]([C:12](=O)[CH:3]([CH2:2][CH3:1])[NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)=[O:24].N[C:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)=[NH:22].[NH2:13][NH2:14]>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[c:12]1[n:13][n:14][c:15](-[c:16]2[cH:17][cH:18][cH:19... | CCOC(=O)C(=O)C(CC)NC(=O)C1CCCC1.N=C(N)c1ccccc1.NN | CCC(NC(=O)C1CCCC1)c1nnc(-c2ccccc2)[nH]c1=O | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | e7bab37df0829099558b3ea1b1d6c14ca29d111a0fe7c4e70294ed15a1035365 | b9a6c12d0e1239b0cb412542e52dae4bfecd4fc5a7cf6f6405348266ba7aff2e | O=C(NCc1nnc(-c2ccccc2)[nH]c1=O)C1CCCC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=O)-[C:4](-[C:5])-[#7:6]-[C:7]=[O;D1;H0:8].N-[C;H0;D3;+0:9](=[NH;D1;+0:10])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15].[NH2;D1;+0:16]-[NH2;D1;+0:17]>>[C:5]-[C:4](-[#7:6]-[C:7]=[O;D1;H0:8])-[c;H0;D3;+0:3]1:[n;H0;D2;+0:16]:[n;H0;D2;+0:17]:[c;H0;D3;+0:9](-[c;H0;D3;+0:11... | null | [] | null | null | 1 | HOUR | 3.5 g (22.3 mmol, 1 equiv.) benzenecarboximidamide hydrochloride are suspended in 10 ml of ethanol and 1.37 g (26.8 mmol, 1.2 equiv.) hydrazine hydrate are added. After stirring at room temperature for 1 hour, 6.28 g (24.6 mmol, 1.1 equiv) of ethyl 3-[(cyclopentylcarbonyl)amino]-2-oxopentanoate (Example 99A), dissolved... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester.Primary amine | null | null | c1cnncn1 | C1CCCC1.c1cnncn1.c1ccccc1 | HO- | C(C)O | null | 1 | CCOC(=O)C(=O)C(CC)NC(=O)C1CCCC1.N=C(N)c1ccccc1.NN>C(C)O>CCC(NC(=O)C1CCCC1)c1nnc(-c2ccccc2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a0112f11c23a4f8d9cf20e8c9624a0a5 | CCC(N)C(=O)O.O=C(Cl)C1CCCC1>>CCC(NC(=O)C1CCCC1)C(=O)O | NC(C(=O)O)CC.Cl[Si](C)(C)C.C1(CCCC1)C(=O)Cl.C(C)N(CC)CC>>C1(CCCC1)C(=O)NC(C(=O)O)CC | [CH3:1][CH2:2][CH:3]([NH2:4])[C:12](=[O:13])[OH:14].Cl[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[C:12](=[O:13])[OH:14] | CCC(N)C(=O)O.O=C(Cl)C1CCCC1 | CCC(NC(=O)C1CCCC1)C(=O)O | null | null | ClCCl.O | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | C1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:8]-[C:7](-[C:6])-[C:9](=[O;D1;H0:10])-[O;D1;H1:11])-[C:5] | null | [] | 0 | CELSIUS | null | null | 35 g (339 mmol) 2-aminobutanoic acid and 75.6 g (747 mmol) triethylamine are suspended in 300 ml of dichloromethane and stirred at 0° C. 81 g (747 mmol) chlorotrimethylsilane are added dropwise, then the mixture is stirred for 1 hour at room temperature and 1 hour at 40° C. After cooling down at −10° C., 45 g (339 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCC1 | HCl | ClCCl.O | 0 | null | CCC(N)C(=O)O.O=C(Cl)C1CCCC1>ClCCl.O>CCC(NC(=O)C1CCCC1)C(=O)O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-806f557d0a9c4151b5de0201eb12a922 | CCC(NC(=O)C1CCCC1)C(=O)O.CCOC(=O)C(=O)Cl>>CCOC(=O)C(=O)C(CC)NC(=O)C1CCCC1 | ClC(C(=O)OCC)=O.C1(CCCC1)C(=O)NC(C(=O)O)CC.N1=CC=CC=C1>>C1(CCCC1)C(=O)NC(C(C(=O)OCC)=O)CC | O[C:6](=[O:7])[CH:8]([CH2:9][CH3:10])[NH:11][C:12](=[O:13])[CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1.O=C(Cl)[C:4]([O:3][CH2:2][CH3:1])=[O:5]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[CH:8]([CH2:9][CH3:10])[NH:11][C:12](=[O:13])[CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1 | CCC(NC(=O)C1CCCC1)C(=O)O.CCOC(=O)C(=O)Cl | CCOC(=O)C(=O)C(CC)NC(=O)C1CCCC1 | null | null | O1CCCC1 | C-C Coupling | Ketonization by decarboxylation of acid halides | aaebaa0d813a71dc889ae147df75d12dcb32900152f1a5154d5b3ca46552ea1b | 3f61ba26fe9791436c27b93d0c669474775a60e3446708a267a9de08824bde1e | C1CCCC1 | Cl-C(=O)-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C:7](-[C:8])-[#7:9]-[C:10]=[O;D1;H0:11]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:5](=[O;D1;H0:6])-[C:7](-[C:8])-[#7:9]-[C:10]=[O;D1;H0:11] | null | [] | null | null | null | null | 1.6 g (8 mmol) 2-[(cyclopentylcarbonyl)amino]butanoic acid are suspended in 30 ml tetrahydrofurane and heated to reflux together with 1.91 g (24 mmol) pyridine and a bit of N,N-dimethylaminopyridine. While heating at reflux, 2.19 g (16 mmol) ethyl chloro(oxo)acetate are added dropwise. The reaction mixture is heated at... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carboxylic acid.Ester | Ketone | null | null | C1CCCC1 | HCl | O1CCCC1 | null | null | CCC(NC(=O)C1CCCC1)C(=O)O.CCOC(=O)C(=O)Cl>O1CCCC1>CCOC(=O)C(=O)C(CC)NC(=O)C1CCCC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3515f6f04b2e4e65bb53076e6c2d4d2c | CCC(N)c1nnc(-c2ccc(C)c3ccccc23)[nH]c1=O.O=C(Cl)C1CCCC1>>CCC(NC(=O)C1CCCC1)c1nnc(-c2ccc(C)c3ccccc23)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1=CC=C(C2=CC=CC=C12)C)=O.C1(CCCC1)C(=O)Cl>>CC1=CC=C(C2=CC=CC=C12)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCCC1 | [CH3:1][CH2:2][CH:3]([NH2:4])[c:12]1[n:13][n:14][c:15](-[c:16]2[cH:17][cH:18][c:19]([CH3:20])[c:21]3[cH:22][cH:23][cH:24][cH:25][c:26]23)[nH:27][c:28]1=[O:29].Cl[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1)[c:12]1[n:13][n:14][c:15](-... | CCC(N)c1nnc(-c2ccc(C)c3ccccc23)[nH]c1=O.O=C(Cl)C1CCCC1 | CCC(NC(=O)C1CCCC1)c1nnc(-c2ccc(C)c3ccccc23)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc(-c2cccc3ccccc23)[nH]c1=O)C1CCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH2;D1;+0:11]):[c:12]:[#7;a:13]>>[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]):[c:12]:[#7;a:13] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 600 mg (2.04 mmol) 6-(1-aminopropyl)-3-(4-methyl-1-naphthyl)-1,2,4-triazin-5(4H)-one, 270 mg (2.04 mmol) cyclopentanecarbonyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Condition... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCC1.c1cnncn1.c1ccc2ccccc2c1 | HCl | null | null | null | CCC(N)c1nnc(-c2ccc(C)c3ccccc23)[nH]c1=O.O=C(Cl)C1CCCC1>>CCC(NC(=O)C1CCCC1)c1nnc(-c2ccc(C)c3ccccc23)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-35fa521300e04d6392407e9a73bd9468 | CC1CC1C(=O)Cl.CCC(N)c1nnc(C2CCCC2)[nH]c1=O>>CCC(NC(=O)C1CC1C)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.CC1C(C1)C(=O)Cl>>C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1C(C1)C | Cl[C:5](=[O:6])[CH:7]1[CH2:8][CH:9]1[CH3:10].[CH3:1][CH2:2][CH:3]([NH2:4])[c:11]1[n:12][n:13][c:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[nH:20][c:21]1=[O:22]>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH:9]1[CH3:10])[c:11]1[n:12][n:13][c:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[nH:20][c:21]1=[O... | CC1CC1C(=O)Cl.CCC(N)c1nnc(C2CCCC2)[nH]c1=O | CCC(NC(=O)C1CC1C)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc(C2CCCC2)[nH]c1=O)C1CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH2;D1;+0:11]):[c:12]:[#7;a:13]>>[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1):[c:12]:[#7;a:13] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 150 mg (0.67 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 90 mg (0.74 mmol) 2-methyl-cyclopropylcarbonyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CC1.c1cnncn1.C1CCCC1 | HCl | null | null | null | CC1CC1C(=O)Cl.CCC(N)c1nnc(C2CCCC2)[nH]c1=O>>CCC(NC(=O)C1CC1C)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a30e5fed5e5f49cb8f81dd65e7fa1170 | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)C1CC1>>CCC(NC(=O)C1CC1)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.C1(CC1)C(=O)Cl>>C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CC1 | [CH3:1][CH2:2][CH:3]([NH2:4])[c:10]1[n:11][n:12][c:13]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18]2)[nH:19][c:20]1=[O:21].Cl[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9]1>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9]1)[c:10]1[n:11][n:12][c:13]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18]2)[nH:19][c:20]1=[O:21] | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)C1CC1 | CCC(NC(=O)C1CC1)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc(C2CCCC2)[nH]c1=O)C1CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1.[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH2;D1;+0:11]):[c:12]:[#7;a:13]>>[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]1-[C:4]-[C:5]-1):[c:12]:[#7;a:13] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 150 mg (0.67 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 80 mg (0.74 mmol) cyclopropylcarbonyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions: See react... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CC1.c1cnncn1.C1CCCC1 | HCl | null | null | null | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)C1CC1>>CCC(NC(=O)C1CC1)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-28aa7bdac7914c36be84fe451cff1059 | CC1CCC(C)(C(=O)Cl)CC1.CCC(N)c1nnc(C2CCCC2)[nH]c1=O>>CCC(NC(=O)C1(C)CCC(C)CC1)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.CC1(CCC(CC1)C)C(=O)Cl>>C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1(CCC(CC1)C)C | Cl[C:5](=[O:6])[C:7]1([CH3:8])[CH2:9][CH2:10][CH:11]([CH3:12])[CH2:13][CH2:14]1.[CH3:1][CH2:2][CH:3]([NH2:4])[c:15]1[n:16][n:17][c:18]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[nH:24][c:25]1=[O:26]>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[C:7]1([CH3:8])[CH2:9][CH2:10][CH:11]([CH3:12])[CH2:13][CH2:14]1)[c:15]1[n:16][n... | CC1CCC(C)(C(=O)Cl)CC1.CCC(N)c1nnc(C2CCCC2)[nH]c1=O | CCC(NC(=O)C1(C)CCC(C)CC1)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc(C2CCCC2)[nH]c1=O)C1CCCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C:5])-[C:6].[#7;a:7]:[#7;a:8]:[c:9](-[C:10](-[C:11])-[NH2;D1;+0:12]):[c:13]:[#7;a:14]>>[#7;a:7]:[#7;a:8]:[c:9](-[C:10](-[C:11])-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C:5])-[C:6]):[c:13]:[#7;a:14] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 150 mg (0.67 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 130 mg (0.74 mmol) 1,4-dimethylcyclohexanecarbonyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditio... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCCC1.c1cnncn1.C1CCCC1 | HCl | null | null | null | CC1CCC(C)(C(=O)Cl)CC1.CCC(N)c1nnc(C2CCCC2)[nH]c1=O>>CCC(NC(=O)C1(C)CCC(C)CC1)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f76a8a8b48e24cfcac66d166cb5a1dec | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)C1CC2C=CC1C2>>CCC(NC(=O)C1CC2C=CC1C2)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.C12C(CC(C=C1)C2)C(=O)Cl>>C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1C2C=CC(C1)C2 | [CH3:1][CH2:2][CH:3]([NH2:4])[c:14]1[n:15][n:16][c:17]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[nH:23][c:24]1=[O:25].Cl[C:5](=[O:6])[CH:7]1[CH2:8][CH:9]2[CH:10]=[CH:11][CH:12]1[CH2:13]2>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH:9]2[CH:10]=[CH:11][CH:12]1[CH2:13]2)[c:14]1[n:15][n:16][c:17]([CH:18]2[CH... | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)C1CC2C=CC1C2 | CCC(NC(=O)C1CC2C=CC1C2)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc(C2CCCC2)[nH]c1=O)C1CC2C=CC1C2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]-[C:6]=[C:7].[#7;a:8]:[#7;a:9]:[c:10](-[C:11](-[C:12])-[NH2;D1;+0:13]):[c:14]:[#7;a:15]>>[#7;a:8]:[#7;a:9]:[c:10](-[C:11](-[C:12])-[NH;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]-[C:6]=[C:7]):[c:14]:[#7;a:15] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 150 mg (0.67 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 120 mg (0.74 mmol) bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Cond... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1=CC2CCC1C2.C1CCCC1.c1cnncn1 | HCl | null | null | null | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)C1CC2C=CC1C2>>CCC(NC(=O)C1CC2C=CC1C2)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b15035c4ddf34d9198f23884b4aa81c0 | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)CC1CC2CCC1C2>>CCC(NC(=O)CC1CC2CCC1C2)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.C12C(CC(CC1)C2)CC(=O)Cl>>C12C(CC(CC1)C2)CC(=O)NC(CC)C=2C(NC(=NN2)C2CCCC2)=O | [CH3:1][CH2:2][CH:3]([NH2:4])[c:15]1[n:16][n:17][c:18]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[nH:24][c:25]1=[O:26].Cl[C:5](=[O:6])[CH2:7][CH:8]1[CH2:9][CH:10]2[CH2:11][CH2:12][CH:13]1[CH2:14]2>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH2:7][CH:8]1[CH2:9][CH:10]2[CH2:11][CH2:12][CH:13]1[CH2:14]2)[c:15]1[n:16][n:17]... | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)CC1CC2CCC1C2 | CCC(NC(=O)CC1CC2CCC1C2)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(CC1CC2CCC1C2)NCc1nnc(C2CCCC2)[nH]c1=O | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]:[#7;a:6]:[c:7](-[C:8](-[C:9])-[NH2;D1;+0:10]):[c:11]:[#7;a:12]>>[#7;a:5]:[#7;a:6]:[c:7](-[C:8](-[C:9])-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]):[c:11]:[#7;a:12] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 150 mg (0.67 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 130 mg (0.74 mmol) bicyclo[2.2.1]hept-2-ylacetyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CC2CCC1C2.C1CCCC1.c1cnncn1 | HCl | null | null | null | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)CC1CC2CCC1C2>>CCC(NC(=O)CC1CC2CCC1C2)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-46d305b2bb144999835a9b8586870ae6 | CC1CCCCC1C(=O)Cl.CCC(N)c1nnc(C2CCCC2)[nH]c1=O>>CCC(NC(=O)C1CCCCC1C)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.CC1C(CCCC1)C(=O)Cl>>C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1C(CCCC1)C | Cl[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH3:13].[CH3:1][CH2:2][CH:3]([NH2:4])[c:14]1[n:15][n:16][c:17]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[nH:23][c:24]1=[O:25]>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH3:13])[c:14]1[n:15][n:16][c:17]([CH:18]2[CH... | CC1CCCCC1C(=O)Cl.CCC(N)c1nnc(C2CCCC2)[nH]c1=O | CCC(NC(=O)C1CCCCC1C)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc(C2CCCC2)[nH]c1=O)C1CCCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH2;D1;+0:11]):[c:12]:[#7;a:13]>>[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]):[c:12]:[#7;a:13] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 150 mg (0.67 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 120 mg (0.74 mmol) 2-methylcyclohexanecarbonyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCCC1.c1cnncn1.C1CCCC1 | HCl | null | null | null | CC1CCCCC1C(=O)Cl.CCC(N)c1nnc(C2CCCC2)[nH]c1=O>>CCC(NC(=O)C1CCCCC1C)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ee542cc51ede45419b3eb6c9c8b4ca47 | CC(C)CC(=O)Cl.CCC(N)c1nnc(C2CCCC2)[nH]c1=O>>CCC(NC(=O)CC(C)C)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.CC(CC(=O)Cl)C>>C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(CC(C)C)=O | Cl[C:5](=[O:6])[CH2:7][CH:8]([CH3:9])[CH3:10].[CH3:1][CH2:2][CH:3]([NH2:4])[c:11]1[n:12][n:13][c:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[nH:20][c:21]1=[O:22]>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH2:7][CH:8]([CH3:9])[CH3:10])[c:11]1[n:12][n:13][c:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[nH:20][c:21]1=... | CC(C)CC(=O)Cl.CCC(N)c1nnc(C2CCCC2)[nH]c1=O | CCC(NC(=O)CC(C)C)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=c1cnnc(C2CCCC2)[nH]1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]:[#7;a:6]:[c:7](-[C:8](-[C:9])-[NH2;D1;+0:10]):[c:11]:[#7;a:12]>>[#7;a:5]:[#7;a:6]:[c:7](-[C:8](-[C:9])-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]):[c:11]:[#7;a:12] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 150 mg (0.67 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 90 mg (0.74 mmol) 3-methylbutanoyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions: See reaction... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cnncn1.C1CCCC1 | HCl | null | null | null | CC(C)CC(=O)Cl.CCC(N)c1nnc(C2CCCC2)[nH]c1=O>>CCC(NC(=O)CC(C)C)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a89b9a449b94af295850bf530e1aab1 | CC1(C(=O)Cl)CCCCC1.CCC(N)c1nnc(C2CCCC2)[nH]c1=O>>CCC(NC(=O)C1(C)CCCCC1)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.CC1(CCCCC1)C(=O)Cl>>C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1(CCCCC1)C | Cl[C:5](=[O:6])[C:7]1([CH3:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1.[CH3:1][CH2:2][CH:3]([NH2:4])[c:14]1[n:15][n:16][c:17]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[nH:23][c:24]1=[O:25]>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[C:7]1([CH3:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)[c:14]1[n:15][n:16][c:17]([CH:18]... | CC1(C(=O)Cl)CCCCC1.CCC(N)c1nnc(C2CCCC2)[nH]c1=O | CCC(NC(=O)C1(C)CCCCC1)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc(C2CCCC2)[nH]c1=O)C1CCCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C:5])-[C:6].[#7;a:7]:[#7;a:8]:[c:9](-[C:10](-[C:11])-[NH2;D1;+0:12]):[c:13]:[#7;a:14]>>[#7;a:7]:[#7;a:8]:[c:9](-[C:10](-[C:11])-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C:5])-[C:6]):[c:13]:[#7;a:14] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 150 mg (0.67 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 120 mg (0.74 mmol) 1-methylcyclohexanecarbonyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCCC1.c1cnncn1.C1CCCC1 | HCl | null | null | null | CC1(C(=O)Cl)CCCCC1.CCC(N)c1nnc(C2CCCC2)[nH]c1=O>>CCC(NC(=O)C1(C)CCCCC1)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-526d21388cd841819a22eea236d08838 | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.CCCCC(=O)Cl>>CCCCC(=O)NC(CC)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.C(CCCC)(=O)Cl>>C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(CCCC)=O | [NH2:7][CH:8]([CH2:9][CH3:10])[c:11]1[n:12][n:13][c:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[nH:20][c:21]1=[O:22].Cl[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])=[O:6]>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5](=[O:6])[NH:7][CH:8]([CH2:9][CH3:10])[c:11]1[n:12][n:13][c:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[nH:20][c:21]1=[O... | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.CCCCC(=O)Cl | CCCCC(=O)NC(CC)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=c1cnnc(C2CCCC2)[nH]1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]:[#7;a:6]:[c:7](-[C:8](-[C:9])-[NH2;D1;+0:10]):[c:11]:[#7;a:12]>>[#7;a:5]:[#7;a:6]:[c:7](-[C:8](-[C:9])-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]):[c:11]:[#7;a:12] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 150 mg (0.67 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 90 mg (0.74 mmol) pentanoyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions: See reaction.notes.... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cnncn1.C1CCCC1 | HCl | null | null | null | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.CCCCC(=O)Cl>>CCCCC(=O)NC(CC)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c41a0bf41f549ef9c4090cba41496dd | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)C12CC3CC(CC(C3)C1)C2>>CCC(NC(=O)C12CC3CC(CC(C3)C1)C2)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.C12(CC3CC(CC(C1)C3)C2)C(=O)Cl>>C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C12CC3CC(CC(C1)C3)C2 | [CH3:1][CH2:2][CH:3]([NH2:4])[c:17]1[n:18][n:19][c:20]([CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)[nH:26][c:27]1=[O:28].Cl[C:5](=[O:6])[C:7]12[CH2:8][CH:9]3[CH2:10][CH:11]([CH2:12][CH:13]([CH2:14]3)[CH2:15]1)[CH2:16]2>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[C:7]12[CH2:8][CH:9]3[CH2:10][CH:11]([CH2:12][CH:13]([CH2:14]3... | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)C12CC3CC(CC(C3)C1)C2 | CCC(NC(=O)C12CC3CC(CC(C3)C1)C2)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=C(NCc1nnc(C2CCCC2)[nH]c1=O)C12CC3CC(CC(C3)C1)C2 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5])-[C:6].[#7;a:7]:[#7;a:8]:[c:9](-[C:10](-[C:11])-[NH2;D1;+0:12]):[c:13]:[#7;a:14]>>[#7;a:7]:[#7;a:8]:[c:9](-[C:10](-[C:11])-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C:5])-[C:6]):[c:13]:[#7;a:14] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 150 mg (0.67 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 150 mg (0.74 mmol) 1-adamantanecarbonyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | C1CCCC1.c1cnncn1.C1C2CC3CC1CC(C2)C3 | HCl | null | null | null | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(Cl)C12CC3CC(CC(C3)C1)C2>>CCC(NC(=O)C12CC3CC(CC(C3)C1)C2)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e8614edd65754b1d8eb7b12fffa62985 | CC(C)(C)C(=O)Cl.CCC(N)c1nnc(C2CCCC2)[nH]c1=O>>CCC(NC(=O)C(C)(C)C)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.CC(C(=O)Cl)(C)C>>C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(C(C)(C)C)=O | Cl[C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[CH3:10].[CH3:1][CH2:2][CH:3]([NH2:4])[c:11]1[n:12][n:13][c:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[nH:20][c:21]1=[O:22]>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[CH3:10])[c:11]1[n:12][n:13][c:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[nH:20][c:21]... | CC(C)(C)C(=O)Cl.CCC(N)c1nnc(C2CCCC2)[nH]c1=O | CCC(NC(=O)C(C)(C)C)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 38143a4d536201990008fd6f2c68e6571a341d1c367481869fbbbe36cb038937 | 0e6ae078978e324f714e184b4f72826d4e3bf2d9ab22d6e9f73740af687be16f | O=c1cnnc(C2CCCC2)[nH]1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6].[#7;a:7]:[#7;a:8]:[c:9](-[C:10](-[C:11])-[NH2;D1;+0:12]):[c:13]:[#7;a:14]>>[#7;a:7]:[#7;a:8]:[c:9](-[C:10](-[C:11])-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[C;D1;H3:5])-[C;D1;H3:6]):[c:13]:[#7;a:14] | null | [] | null | null | null | null | In analogy to the procedure for Example 36A, 150 mg (0.67 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 90 mg (0.74 mmol) 2,2-dimethylpropanoyl chloride and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions: See rea... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Secondary amide | null | null | c1cnncn1.C1CCCC1 | HCl | null | null | null | CC(C)(C)C(=O)Cl.CCC(N)c1nnc(C2CCCC2)[nH]c1=O>>CCC(NC(=O)C(C)(C)C)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5df41889bf2647ffb1b74693fb65d127 | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(O)CC1CCCCC1>>CCC(NC(=O)CC1CCCCC1)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.C1(CCCCC1)CC(=O)O>>C1(CCCCC1)CC(=O)NC(CC)C=1C(NC(=NN1)C1CCCC1)=O | [CH3:1][CH2:2][CH:3]([NH2:4])[c:14]1[n:15][n:16][c:17]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[nH:23][c:24]1=[O:25].O[C:5](=[O:6])[CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH2:7][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1)[c:14]1[n:15][n:16][c:17]([CH:18]2[C... | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(O)CC1CCCCC1 | CCC(NC(=O)CC1CCCCC1)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CC1CCCCC1)NCc1nnc(C2CCCC2)[nH]c1=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]:[#7;a:6]:[c:7](-[C:8](-[C:9])-[NH2;D1;+0:10]):[c:11]:[#7;a:12]>>[#7;a:5]:[#7;a:6]:[c:7](-[C:8](-[C:9])-[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]):[c:11]:[#7;a:12] | null | [] | null | null | null | null | In analogy to the procedure for Example 58A, 150 mg (0.67 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 96 mg (0.67 mmol) cyclo-hexylacetic acid and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions: See reaction.no... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CCCCC1.c1cnncn1.C1CCCC1 | HO- | null | null | null | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(O)CC1CCCCC1>>CCC(NC(=O)CC1CCCCC1)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3f2cd2959e904a97af7642782a93832e | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.CCCCC(CC)C(=O)O>>CCCCC(CC)C(=O)NC(CC)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.C(C)C(C(=O)O)CCCC>>C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(C(CCCC)CC)=O | [NH2:10][CH:11]([CH2:12][CH3:13])[c:14]1[n:15][n:16][c:17]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[nH:23][c:24]1=[O:25].O[C:8]([CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH3:7])=[O:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[C:8](=[O:9])[NH:10][CH:11]([CH2:12][CH3:13])[c:14]1[n:15][n:16][c:17]([CH:18]2[C... | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.CCCCC(CC)C(=O)O | CCCCC(CC)C(=O)NC(CC)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=c1cnnc(C2CCCC2)[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH2;D1;+0:11]):[c:12]:[#7;a:13]>>[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]):[c:12]:[#7;a:13] | null | [] | null | null | null | null | In analogy to the procedure for Example 58A, 150 mg (0.67 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 97 mg (0.67 mmol) 2-ethyl-hexanoic acid and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cnncn1.C1CCCC1 | HO- | null | null | null | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.CCCCC(CC)C(=O)O>>CCCCC(CC)C(=O)NC(CC)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-035d364ace0543c9b021e13a63212a86 | CCC(C)(C)C(=O)O.CCC(N)c1nnc(C2CCCC2)[nH]c1=O>>CCC(NC(=O)C(C)(C)CC)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.CC(C(=O)O)(CC)C>>C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(C(CC)(C)C)=O | O[C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[CH2:10][CH3:11].[CH3:1][CH2:2][CH:3]([NH2:4])[c:12]1[n:13][n:14][c:15]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[nH:21][c:22]1=[O:23]>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[CH2:10][CH3:11])[c:12]1[n:13][n:14][c:15]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]... | CCC(C)(C)C(=O)O.CCC(N)c1nnc(C2CCCC2)[nH]c1=O | CCC(NC(=O)C(C)(C)CC)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=c1cnnc(C2CCCC2)[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[C;D1;H3:6].[#7;a:7]:[#7;a:8]:[c:9](-[C:10](-[C:11])-[NH2;D1;+0:12]):[c:13]:[#7;a:14]>>[#7;a:7]:[#7;a:8]:[c:9](-[C:10](-[C:11])-[NH;D2;+0:12]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])(-[C;D1;H3:5])-[C;D1;H3:6]):[c:13]:[#7;a:14] | null | [] | null | null | null | null | In analogy to the procedure for Example 58A, 150 mg (0.67 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 78 mg (0.67 mmol) 2,2-dimethylbutanoic acid and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purification.
Conditions: See reaction... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cnncn1.C1CCCC1 | HO- | null | null | null | CCC(C)(C)C(=O)O.CCC(N)c1nnc(C2CCCC2)[nH]c1=O>>CCC(NC(=O)C(C)(C)CC)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c64acda377b04231a8bd09f8e64f3cb5 | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1>>CCC(NC(=O)C1CCN(C(=O)OCc2ccccc2)CC1)c1nnc(C2CCCC2)[nH]c1=O | NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)C(=O)O>>C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCN(CC1)C(=O)OCC1=CC=CC=C1 | [CH3:1][CH2:2][CH:3]([NH2:4])[c:23]1[n:24][n:25][c:26]([CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31]2)[nH:32][c:33]1=[O:34].O[C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][N:10]([C:11](=[O:12])[O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>>[CH3:1][CH2:2][CH:3]([NH:4][C:5](=[O:6])[CH:7]1[CH2:8][CH2:9][N:10]... | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1 | CCC(NC(=O)C1CCN(C(=O)OCc2ccccc2)CC1)c1nnc(C2CCCC2)[nH]c1=O | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCc1nnc(C2CCCC2)[nH]c1=O)C1CCN(C(=O)OCc2ccccc2)CC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH2;D1;+0:11]):[c:12]:[#7;a:13]>>[#7;a:6]:[#7;a:7]:[c:8](-[C:9](-[C:10])-[NH;D2;+0:11]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5]):[c:12]:[#7;a:13] | null | [] | null | null | null | null | In analogy to the procedure for Example 58A, 300 mg (1.35 mmol) 6-(1-aminopropyl)-3-cyclopentyl-1,2,4-triazin-5(4H)-one, 355 mg (1.35 mmol) 1-[(benzyloxy)carbonyl]-4-piperidinecarboxylic acid and proportionate amounts of the other reagents are used. The crude product is used in the next step without further purificatio... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | C1CC[NH]CC1.c1ccccc1.c1cnncn1.C1CCCC1 | HO- | null | null | null | CCC(N)c1nnc(C2CCCC2)[nH]c1=O.O=C(O)C1CCN(C(=O)OCc2ccccc2)CC1>>CCC(NC(=O)C1CCN(C(=O)OCc2ccccc2)CC1)c1nnc(C2CCCC2)[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-51030bc0c1e8473286edfced07098f01 | CCC(NC(=O)C1CCCC1)c1nnc(-c2ccc(Br)cc2)[nH]c1=O>>CCc1nc(C2CCCC2)n2nc(-c3ccc(Br)cc3)[nH]c(=O)c12 | BrC1=CC=C(C=C1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCCC1.P(=O)(Cl)(Cl)Cl>>BrC1=CC=C(C=C1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:24]1[n:11][n:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]2)[nH:21][c:22]1=[O:23])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[n:11]2[n:12][c:13](-[c:14]3[cH:15][cH:16][c:17]([Br:18])[cH:19][cH:20]3)[n... | CCC(NC(=O)C1CCCC1)c1nnc(-c2ccc(Br)cc2)[nH]c1=O | CCc1nc(C2CCCC2)n2nc(-c3ccc(Br)cc3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCC3)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C:14])-[C:15]>>[C:14]-[C:13](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#7;a:10]:[c:9]:[#7;a:8]:[n;H0;D3;+0:7]:2:1)-[C:15] | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 2.34 g (5.77 mmol) N-{1-[3-(4-bromophenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}cyclopentanecarboxamide, 4.43 g (28.9 mmol) phosphoric trichloride are stirred at reflux for 3 hours, proportionate amounts of the solvents are used.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CCCC1.c1ncc2cncn2n1.c1ccccc1 | HO- | null | null | null | CCC(NC(=O)C1CCCC1)c1nnc(-c2ccc(Br)cc2)[nH]c1=O>>CCc1nc(C2CCCC2)n2nc(-c3ccc(Br)cc3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0400fe8fcaba4d8bac5afc40be9e5cd1 | CCC(NC(=O)C1CCC1)c1nnc(C2CC2)[nH]c1=O>>CCc1nc(C2CCC2)n2nc(C3CC3)[nH]c(=O)c12 | C1(CC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCC1.P(=O)(Cl)(Cl)Cl>>C1(CCC1)C1=NC(=C2C(NC(=NN21)C2CC2)=O)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:19]1[n:10][n:11][c:12]([CH:13]2[CH2:14][CH2:15]2)[nH:16][c:17]1=[O:18])[CH:6]1[CH2:7][CH2:8][CH2:9]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9]2)[n:10]2[n:11][c:12]([CH:13]3[CH2:14][CH2:15]3)[nH:16][c:17](=[O:18])[c:19]12 | CCC(NC(=O)C1CCC1)c1nnc(C2CC2)[nH]c1=O | CCc1nc(C2CCC2)n2nc(C3CC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CC2)nn2c(C3CCC3)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C:14])-[C:15]>>[C:14]-[C:13](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#7;a:10]:[c:9]:[#7;a:8]:[n;H0;D3;+0:7]:2:1)-[C:15] | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 350 mg (1.28 mmol) crude N-[1-(3-cyclopropyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]cyclobutanecarboxamide, 200 mg (1.28 mmol) phosphoric trichloride are stirred at reflux for 3 hours, proportionate amounts of the solvents are used.
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CCC1.c1ncc2cncn2n1.C1CC1 | HO- | null | null | null | CCC(NC(=O)C1CCC1)c1nnc(C2CC2)[nH]c1=O>>CCc1nc(C2CCC2)n2nc(C3CC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-644fc957d9a84e2ba138f5e61c9a83ef | CCC(NC(=O)C1CCCC1)c1nnc(C2CC2)[nH]c1=O>>CCc1nc(C2CCCC2)n2nc(C3CC3)[nH]c(=O)c12 | C1(CC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCCC1.P(=O)(Cl)(Cl)Cl>>C1(CCCC1)C1=NC(=C2C(NC(=NN21)C2CC2)=O)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:20]1[n:11][n:12][c:13]([CH:14]2[CH2:15][CH2:16]2)[nH:17][c:18]1=[O:19])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[n:11]2[n:12][c:13]([CH:14]3[CH2:15][CH2:16]3)[nH:17][c:18](=[O:19])[c:20]12 | CCC(NC(=O)C1CCCC1)c1nnc(C2CC2)[nH]c1=O | CCc1nc(C2CCCC2)n2nc(C3CC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CC2)nn2c(C3CCCC3)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C:14])-[C:15]>>[C:14]-[C:13](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#7;a:10]:[c:9]:[#7;a:8]:[n;H0;D3;+0:7]:2:1)-[C:15] | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 370 mg (1.28 mmol) crude N-[1-(3-cyclopropyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]cyclopentanecarboxamide, 200 mg (1.28 mmol) phosphoric trichloride are stirred at reflux for 3 hours, proportionate amounts of the solvents are used.
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CCCC1.c1ncc2cncn2n1.C1CC1 | HO- | null | null | null | CCC(NC(=O)C1CCCC1)c1nnc(C2CC2)[nH]c1=O>>CCc1nc(C2CCCC2)n2nc(C3CC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c462ab3399b44288913d58477018dab0 | CCC(NC(=O)C1CCCC1)c1nnc(C(C)(C)C)[nH]c1=O>>CCc1nc(C2CCCC2)n2nc(C(C)(C)C)[nH]c(=O)c12 | C(C)(C)(C)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCCC1.P(=O)(Cl)(Cl)Cl>>C(C)(C)(C)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:21]1[n:11][n:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[nH:18][c:19]1=[O:20])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[n:11]2[n:12][c:13]([C:14]([CH3:15])([CH3:16])[CH3:17])[nH:18][c:19](=[O:20])[c:21]12 | CCC(NC(=O)C1CCCC1)c1nnc(C(C)(C)C)[nH]c1=O | CCc1nc(C2CCCC2)n2nc(C(C)(C)C)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]cnn2c(C3CCCC3)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C:14])-[C:15]>>[C:14]-[C:13](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#7;a:10]:[c:9]:[#7;a:8]:[n;H0;D3;+0:7]:2:1)-[C:15] | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 150 mg (0.50 mmol) crude N-[1-(3-tert-butyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]cyclopentanecarboxamide, 80 mg (0.50 mmol) phosphoric trichloride are stirred at reflux for 3 hours, proportionate amounts of the solvents are used.
Conditions: See reaction.notes.procedure... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CCCC1.c1ncc2cncn2n1 | HO- | null | null | null | CCC(NC(=O)C1CCCC1)c1nnc(C(C)(C)C)[nH]c1=O>>CCc1nc(C2CCCC2)n2nc(C(C)(C)C)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-cf45ab27f34c4f82a0dd0b3275ab9fd7 | CCC(NC(=O)C1CCC1)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2CCC2)n2nc(C3CCCC3)[nH]c(=O)c12 | C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCC1.P(=O)(Cl)(Cl)Cl>>C1(CCC1)C1=NC(=C2C(NC(=NN21)C2CCCC2)=O)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:21]1[n:10][n:11][c:12]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)[nH:18][c:19]1=[O:20])[CH:6]1[CH2:7][CH2:8][CH2:9]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9]2)[n:10]2[n:11][c:12]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[nH:18][c:19](=[O:20])[c:21]12 | CCC(NC(=O)C1CCC1)c1nnc(C2CCCC2)[nH]c1=O | CCc1nc(C2CCC2)n2nc(C3CCCC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CCCC2)nn2c(C3CCC3)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C:14])-[C:15]>>[C:14]-[C:13](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#7;a:10]:[c:9]:[#7;a:8]:[n;H0;D3;+0:7]:2:1)-[C:15] | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 270 mg (0.90 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]cyclobutanecarboxamide, 140 mg (0.90 mmol) phosphoric trichloride are stirred at reflux for 3 hours, proportionate amounts of the solvents are used.
Conditions: See reaction.notes.procedur... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CCC1.c1ncc2cncn2n1.C1CCCC1 | HO- | null | null | null | CCC(NC(=O)C1CCC1)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2CCC2)n2nc(C3CCCC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b416efe0b1cf4f3b91ebf5f5d14dabb6 | CCC(NC(=O)C1CCCC1)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2CCCC2)n2nc(C3CCCC3)[nH]c(=O)c12 | C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCCC1.P(=O)(Cl)(Cl)Cl>>C1(CCCC1)C1=NN2C(C(N1)=O)=C(N=C2C2CCCC2)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:22]1[n:11][n:12][c:13]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18]2)[nH:19][c:20]1=[O:21])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[n:11]2[n:12][c:13]([CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[nH:19][c:20](=[O:21])[c... | CCC(NC(=O)C1CCCC1)c1nnc(C2CCCC2)[nH]c1=O | CCc1nc(C2CCCC2)n2nc(C3CCCC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CCCC2)nn2c(C3CCCC3)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C:14])-[C:15]>>[C:14]-[C:13](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#7;a:10]:[c:9]:[#7;a:8]:[n;H0;D3;+0:7]:2:1)-[C:15] | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 290 mg (0.90 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]cyclopentanecarboxamide, 140 mg (0.90 mmol) phosphoric trichloride are stirred at reflux for 3 hours, proportionate amounts of the solvents are used.
Conditions: See reaction.notes.procedu... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CCCC1.c1ncc2cncn2n1.C1CCCC1 | HO- | null | null | null | CCC(NC(=O)C1CCCC1)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2CCCC2)n2nc(C3CCCC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-957348d4cf7349169adb2c6f0a7e9edb | CCC(NC(=O)C1CCCC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O>>CCc1nc(C2CCCC2)n2nc(-c3cccc([N+](=O)[O-])c3)[nH]c(=O)c12 | [N+](=O)([O-])C=1C=C(C=CC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCCC1.P(=O)(Cl)(Cl)Cl>>C1(CCCC1)C1=NC(=C2C(NC(=NN21)C2=CC(=CC=C2)[N+](=O)[O-])=O)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:26]1[n:11][n:12][c:13](-[c:14]2[cH:15][cH:16][cH:17][c:18]([N+:19](=[O:20])[O-:21])[cH:22]2)[nH:23][c:24]1=[O:25])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[n:11]2[n:12][c:13](-[c:14]3[cH:15][cH:16][cH:17][c:18]([N+... | CCC(NC(=O)C1CCCC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O | CCc1nc(C2CCCC2)n2nc(-c3cccc([N+](=O)[O-])c3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(-c2ccccc2)nn2c(C3CCCC3)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C:14])-[C:15]>>[C:14]-[C:13](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#7;a:10]:[c:9]:[#7;a:8]:[n;H0;D3;+0:7]:2:1)-[C:15] | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 3.5 g (9.4 mmol) N-{1-[3-(3-nitrophenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}cyclopentanecarboxamide, 1.45 g (9.4 mmol) phosphoric trichloride are stirred at reflux for 3 hours, proportionate amounts of the solvents are used.
Conditions: See reaction.notes.procedure_de... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CCCC1.c1ncc2cncn2n1.c1ccccc1 | HO- | null | null | null | CCC(NC(=O)C1CCCC1)c1nnc(-c2cccc([N+](=O)[O-])c2)[nH]c1=O>>CCc1nc(C2CCCC2)n2nc(-c3cccc([N+](=O)[O-])c3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c9227ef32614a76914c4f2107bb68e9 | CCC(NC(=O)C1CCCC1)c1nnc(-c2ccc(C)c3ccccc23)[nH]c1=O>>CCc1nc(C2CCCC2)n2nc(-c3ccc(C)c4ccccc34)[nH]c(=O)c12 | CC1=CC=C(C2=CC=CC=C12)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCCC1.P(=O)(Cl)(Cl)Cl>>C1(CCCC1)C1=NC(=C2C(NC(=NN21)C2=CC=C(C1=CC=CC=C21)C)=O)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:28]1[n:11][n:12][c:13](-[c:14]2[cH:15][cH:16][c:17]([CH3:18])[c:19]3[cH:20][cH:21][cH:22][cH:23][c:24]23)[nH:25][c:26]1=[O:27])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]2)[n:11]2[n:12][c:13](-[c:14]3[cH:15][cH:16][c:1... | CCC(NC(=O)C1CCCC1)c1nnc(-c2ccc(C)c3ccccc23)[nH]c1=O | CCc1nc(C2CCCC2)n2nc(-c3ccc(C)c4ccccc34)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(-c2cccc3ccccc23)nn2c(C3CCCC3)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C:14])-[C:15]>>[C:14]-[C:13](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#7;a:10]:[c:9]:[#7;a:8]:[n;H0;D3;+0:7]:2:1)-[C:15] | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 797 mg (2.04 mmol) crude N-{1-[3-(4-methyl-1-naphthyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]propyl}cyclopentanecarboxamide, 469 mg (3.06 mmol) phosphoric trichloride are stirred at reflux for 3 hours, proportionate amounts of the solvents are used.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CCCC1.c1ncc2cncn2n1.c1ccc2ccccc2c1 | HO- | null | null | null | CCC(NC(=O)C1CCCC1)c1nnc(-c2ccc(C)c3ccccc23)[nH]c1=O>>CCc1nc(C2CCCC2)n2nc(-c3ccc(C)c4ccccc34)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c6d0c18f8ded43c484f88d5c0477190e | CCC(NC(=O)C1CC1C)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2CC2C)n2nc(C3CCCC3)[nH]c(=O)c12 | C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1C(C1)C.P(=O)(Cl)(Cl)Cl>>C1(CCCC1)C1=NN2C(C(N1)=O)=C(N=C2C2C(C2)C)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:21]1[n:10][n:11][c:12]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)[nH:18][c:19]1=[O:20])[CH:6]1[CH2:7][CH:8]1[CH3:9]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH:8]2[CH3:9])[n:10]2[n:11][c:12]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[nH:18][c:19](=[O:20])[c:21]12 | CCC(NC(=O)C1CC1C)c1nnc(C2CCCC2)[nH]c1=O | CCc1nc(C2CC2C)n2nc(C3CCCC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CCCC2)nn2c(C3CC3)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13]1-[C:14]-[C:15]-1>>[C;D1;H3:5]-[C:4]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:1](-[C:13]2-[C:14]-[C:15]-2):[n;H0;D3;+0:7]2:[#7;a:8]:[c:9]:[#7;a:10]:[c:11](=[O;D1;H0:12]):[c:6]:1:... | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 200 mg (0.66 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]-2-methylcyclopropanecarboxamide, 165 mg (1.1 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The isomers are purified by ch... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CC1.c1ncc2cncn2n1.C1CCCC1 | HO- | null | null | null | CCC(NC(=O)C1CC1C)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2CC2C)n2nc(C3CCCC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a3d02565fc4f4a5aa7c72e5530687638 | CCC(NC(=O)C1CC1)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2CC2)n2nc(C3CCCC3)[nH]c(=O)c12 | C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CC1.P(=O)(Cl)(Cl)Cl>>C1(CCCC1)C1=NN2C(C(N1)=O)=C(N=C2C2CC2)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:20]1[n:9][n:10][c:11]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16]2)[nH:17][c:18]1=[O:19])[CH:6]1[CH2:7][CH2:8]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8]2)[n:9]2[n:10][c:11]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[nH:17][c:18](=[O:19])[c:20]12 | CCC(NC(=O)C1CC1)c1nnc(C2CCCC2)[nH]c1=O | CCc1nc(C2CC2)n2nc(C3CCCC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CCCC2)nn2c(C3CC3)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13]1-[C:14]-[C:15]-1>>[C;D1;H3:5]-[C:4]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:1](-[C:13]2-[C:14]-[C:15]-2):[n;H0;D3;+0:7]2:[#7;a:8]:[c:9]:[#7;a:10]:[c:11](=[O;D1;H0:12]):[c:6]:1:... | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 200 mg (0.66 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]cyclopropanecarboxamide, 165 mg (1.1 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The product is purified by chromatograp... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CC1.c1ncc2cncn2n1.C1CCCC1 | HO- | null | null | null | CCC(NC(=O)C1CC1)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2CC2)n2nc(C3CCCC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-47ef90e7701b42c490237547e70918d4 | CCC(NC(=O)C1(C)CCC(C)CC1)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2(C)CCC(C)CC2)n2nc(C3CCCC3)[nH]c(=O)c12 | C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1(CCC(CC1)C)C.P(=O)(Cl)(Cl)Cl>>C1(CCCC1)C1=NN2C(C(N1)=O)=C(N=C2C2(CCC(CC2)C)C)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:25]1[n:14][n:15][c:16]([CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[nH:22][c:23]1=[O:24])[C:6]1([CH3:7])[CH2:8][CH2:9][CH:10]([CH3:11])[CH2:12][CH2:13]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([C:6]2([CH3:7])[CH2:8][CH2:9][CH:10]([CH3:11])[CH2:12][CH2:13]2)[n:14]2[n:15][c:16]([CH:17]3[CH2:1... | CCC(NC(=O)C1(C)CCC(C)CC1)c1nnc(C2CCCC2)[nH]c1=O | CCc1nc(C2(C)CCC(C)CC2)n2nc(C3CCCC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CCCC2)nn2c(C3CCCCC3)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C;D1;H3:14])(-[C:15])-[C:16]>>[C:15]-[C:13](-[C;D1;H3:14])(-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#7;a:10]:[c:9]:[#7;a:... | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 200 mg (0.55 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]-1,4-dimethylcyclohexanecarboxamide, 165 mg (1.1 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The isomers are purified by... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CCCCC1.c1ncc2cncn2n1.C1CCCC1 | HO- | null | null | null | CCC(NC(=O)C1(C)CCC(C)CC1)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2(C)CCC(C)CC2)n2nc(C3CCCC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f94205c2ea4a4c8380418be35042d758 | CCC(NC(=O)C1CC2C=CC1C2)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2CC3C=CC2C3)n2nc(C3CCCC3)[nH]c(=O)c12 | C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1C2C=CC(C1)C2.P(=O)(Cl)(Cl)Cl>>C12C(CC(C=C1)C2)C2=NC(=C1C(NC(=NN12)C1CCCC1)=O)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:24]1[n:13][n:14][c:15]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[nH:21][c:22]1=[O:23])[CH:6]1[CH2:7][CH:8]2[CH:9]=[CH:10][CH:11]1[CH2:12]2>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH:8]3[CH:9]=[CH:10][CH:11]2[CH2:12]3)[n:13]2[n:14][c:15]([CH:16]3[CH2:17][CH2:18][CH2:19][CH2... | CCC(NC(=O)C1CC2C=CC1C2)c1nnc(C2CCCC2)[nH]c1=O | CCc1nc(C2CC3C=CC2C3)n2nc(C3CCCC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CCCC2)nn2c(C3CC4C=CC3C4)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C:14])-[C:15]-[C:16]=[C:17]>>[C:14]-[C:13](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#7;a:10]:[c:9]:[#7;a:8]:[n;H0;D3;+0:7... | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 200 mg (0.58 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]bicyclo[2.2.1]hept-5-ene-2-carboxamide, 165 mg (1.1 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The isomers are purified... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1=CC2CCC1C2.C1CCCC1.c1ncc2cncn2n1 | HO- | null | null | null | CCC(NC(=O)C1CC2C=CC1C2)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2CC3C=CC2C3)n2nc(C3CCCC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-10735c9d20bb40cd8277b789c9878804 | CCC(NC(=O)CC1CC2CCC1C2)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(CC2CC3CCC2C3)n2nc(C3CCCC3)[nH]c(=O)c12 | C12C(CC(CC1)C2)CC(=O)NC(CC)C=2C(NC(=NN2)C2CCCC2)=O.P(=O)(Cl)(Cl)Cl>>C12C(CC(CC1)C2)CC2=NC(=C1C(NC(=NN12)C1CCCC1)=O)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:25]1[n:14][n:15][c:16]([CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[nH:22][c:23]1=[O:24])[CH2:6][CH:7]1[CH2:8][CH:9]2[CH2:10][CH2:11][CH:12]1[CH2:13]2>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH2:6][CH:7]2[CH2:8][CH:9]3[CH2:10][CH2:11][CH:12]2[CH2:13]3)[n:14]2[n:15][c:16]([CH:17]3[CH2:18][C... | CCC(NC(=O)CC1CC2CCC1C2)c1nnc(C2CCCC2)[nH]c1=O | CCc1nc(CC2CC3CCC2C3)n2nc(C3CCCC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CCCC2)nn2c(CC3CC4CCC3C4)ncc12 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[NH;D2;+0:4]-[CH;D3;+0:5](-[C:6]-[C;D1;H3:7])-[c:8]1:[n;H0;D2;+0:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1=[O;D1;H0:14]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-[C:6]-[C;D1;H3:7]):[c:8]2:[c:13](=[O;D1;H0:14]):[#7;a:12]:[c:11]:[#7;a:10]:[n;H0;D3;+0:9]:2:1 | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 200 mg (0.56 mmol) crude 2-bicyclo[2.2.1]hept-2-yl-N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)-propyl]acetamide, 165 mg (1.1 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The product is purified by... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CC2CCC1C2.C1CCCC1.c1ncc2cncn2n1 | HO- | null | null | null | CCC(NC(=O)CC1CC2CCC1C2)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(CC2CC3CCC2C3)n2nc(C3CCCC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ef45c28416254026af4c7d872c8778db | CCC(NC(=O)C1CCCCC1C)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2CCCCC2C)n2nc(C3CCCC3)[nH]c(=O)c12 | C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1C(CCCC1)C.P(=O)(Cl)(Cl)Cl>>C1(CCCC1)C1=NN2C(C(N1)=O)=C(N=C2C2C(CCCC2)C)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:24]1[n:13][n:14][c:15]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[nH:21][c:22]1=[O:23])[CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH3:12]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH:11]2[CH3:12])[n:13]2[n:14][c:15]([CH:16]3[CH2:17][CH2:18][CH2:19][CH2... | CCC(NC(=O)C1CCCCC1C)c1nnc(C2CCCC2)[nH]c1=O | CCc1nc(C2CCCCC2C)n2nc(C3CCCC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CCCC2)nn2c(C3CCCCC3)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C:14])-[C:15]>>[C:14]-[C:13](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#7;a:10]:[c:9]:[#7;a:8]:[n;H0;D3;+0:7]:2:1)-[C:15] | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 200 mg (0.58 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]-2-methylcyclohexanecarboxamide, 165 mg (1.1 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The isomers are purified by chr... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CCCCC1.c1ncc2cncn2n1.C1CCCC1 | HO- | null | null | null | CCC(NC(=O)C1CCCCC1C)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2CCCCC2C)n2nc(C3CCCC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c5798c17b447441b9e4060d433aabf09 | CCC(NC(=O)CC(C)C)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(CC(C)C)n2nc(C3CCCC3)[nH]c(=O)c12 | C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(CC(C)C)=O.P(=O)(Cl)(Cl)Cl>>C1(CCCC1)C1=NN2C(C(N1)=O)=C(N=C2CC(C)C)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:21]1[n:10][n:11][c:12]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)[nH:18][c:19]1=[O:20])[CH2:6][CH:7]([CH3:8])[CH3:9]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH2:6][CH:7]([CH3:8])[CH3:9])[n:10]2[n:11][c:12]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[nH:18][c:19](=[O:20])[c:21]12 | CCC(NC(=O)CC(C)C)c1nnc(C2CCCC2)[nH]c1=O | CCc1nc(CC(C)C)n2nc(C3CCCC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CCCC2)nn2cncc12 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[NH;D2;+0:4]-[CH;D3;+0:5](-[C:6]-[C;D1;H3:7])-[c:8]1:[n;H0;D2;+0:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1=[O;D1;H0:14]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-[C:6]-[C;D1;H3:7]):[c:8]2:[c:13](=[O;D1;H0:14]):[#7;a:12]:[c:11]:[#7;a:10]:[n;H0;D3;+0:9]:2:1 | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 200 mg (0.65 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]-3-methylbutanamide, 165 mg (1.1 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The product is purified by chromatography (... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | c1ncc2cncn2n1.C1CCCC1 | HO- | null | null | null | CCC(NC(=O)CC(C)C)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(CC(C)C)n2nc(C3CCCC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f58a7fb0b87a4cadabcb3f41487c1aa6 | CCC(NC(=O)C1(C)CCCCC1)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2(C)CCCCC2)n2nc(C3CCCC3)[nH]c(=O)c12 | C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1(CCCCC1)C.P(=O)(Cl)(Cl)Cl>>C1(CCCC1)C1=NN2C(C(N1)=O)=C(N=C2C2(CCCCC2)C)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:24]1[n:13][n:14][c:15]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[nH:21][c:22]1=[O:23])[C:6]1([CH3:7])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([C:6]2([CH3:7])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[n:13]2[n:14][c:15]([CH:16]3[CH2:17][CH2:18][CH2:19]... | CCC(NC(=O)C1(C)CCCCC1)c1nnc(C2CCCC2)[nH]c1=O | CCc1nc(C2(C)CCCCC2)n2nc(C3CCCC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CCCC2)nn2c(C3CCCCC3)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C;D1;H3:14])(-[C:15])-[C:16]>>[C:15]-[C:13](-[C;D1;H3:14])(-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#7;a:10]:[c:9]:[#7;a:... | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 200 mg (0.58 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]-1-methylcyclohexanecarboxamide, 165 mg (1.1 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The product is purified by chro... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CCCCC1.c1ncc2cncn2n1.C1CCCC1 | HO- | null | null | null | CCC(NC(=O)C1(C)CCCCC1)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2(C)CCCCC2)n2nc(C3CCCC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8382ac1c71f34947b8e5d63f5d6890bb | CCCCC(=O)NC(CC)c1nnc(C2CCCC2)[nH]c1=O>>CCCCc1nc(CC)c2c(=O)[nH]c(C3CCCC3)nn12 | C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(CCCC)=O.P(=O)(Cl)(Cl)Cl>>C(CCC)C1=NC(=C2C(NC(=NN21)C2CCCC2)=O)CC | O=[C:5]([CH2:4][CH2:3][CH2:2][CH3:1])[NH:6][CH:7]([CH2:8][CH3:9])[c:10]1[c:11](=[O:12])[nH:13][c:14]([CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[n:20][n:21]1>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([CH2:8][CH3:9])[c:10]2[c:11](=[O:12])[nH:13][c:14]([CH:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)[n:20][n:21]12 | CCCCC(=O)NC(CC)c1nnc(C2CCCC2)[nH]c1=O | CCCCc1nc(CC)c2c(=O)[nH]c(C3CCCC3)nn12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CCCC2)nn2cncc12 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[NH;D2;+0:4]-[CH;D3;+0:5](-[C:6]-[C;D1;H3:7])-[c:8]1:[n;H0;D2;+0:9]:[#7;a:10]:[c:11](-[C:12]):[#7;a:13]:[c:14]:1=[O;D1;H0:15]>>[C:12]-[c:11]1:[#7;a:13]:[c:14](=[O;D1;H0:15]):[c:8]2:[c;H0;D3;+0:5](-[C:6]-[C;D1;H3:7]):[n;H0;D2;+0:4]:[c;H0;D3;+0:1](-[C:2]-[C:3]):[n;H0;D3;+0:9]:2:[#7;a:10]:1 | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 200 mg (0.65 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]pentanamide, 165 mg (1.1 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The product is purified by chromatography (preparat... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | c1ncc2cncn2n1.C1CCCC1 | HO- | null | null | null | CCCCC(=O)NC(CC)c1nnc(C2CCCC2)[nH]c1=O>>CCCCc1nc(CC)c2c(=O)[nH]c(C3CCCC3)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-06d291966cce4ad0bd1551ebc0ed2ff5 | CCC(NC(=O)C12CC3CC(CC(C3)C1)C2)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C23CC4CC(CC(C4)C2)C3)n2nc(C3CCCC3)[nH]c(=O)c12 | C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C12CC3CC(CC(C1)C3)C2.P(=O)(Cl)(Cl)Cl>>C12(CC3CC(CC(C1)C3)C2)C2=NC(=C3C(NC(=NN32)C3CCCC3)=O)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:27]1[n:16][n:17][c:18]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[nH:24][c:25]1=[O:26])[C:6]12[CH2:7][CH:8]3[CH2:9][CH:10]([CH2:11][CH:12]([CH2:13]3)[CH2:14]1)[CH2:15]2>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([C:6]23[CH2:7][CH:8]4[CH2:9][CH:10]([CH2:11][CH:12]([CH2:13]4)[CH2:14]2)[CH2:15]... | CCC(NC(=O)C12CC3CC(CC(C3)C1)C2)c1nnc(C2CCCC2)[nH]c1=O | CCc1nc(C23CC4CC(CC(C4)C2)C3)n2nc(C3CCCC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CCCC2)nn2c(C34CC5CC(CC(C5)C3)C4)ncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C:14])(-[C:15])-[C:16]>>[C:14]-[C:13](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#7;a:10]:[c:9]:[#7;a:8]:[n;H0;D3;+0:7]:2:1... | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 200 mg (0.52 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]-1-adamantanecarboxamide, 165 mg (1.1 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The product is purified by chromatogra... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CCCC1.c1ncc2cncn2n1.C1C2CC3CC1CC(C2)C3 | HO- | null | null | null | CCC(NC(=O)C12CC3CC(CC(C3)C1)C2)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C23CC4CC(CC(C4)C2)C3)n2nc(C3CCCC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b71c7023922d46f59dfb9a9827d34d81 | CCC(NC(=O)C(C)(C)C)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C(C)(C)C)n2nc(C3CCCC3)[nH]c(=O)c12 | C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(C(C)(C)C)=O.P(=O)(Cl)(Cl)Cl>>C(C)(C)(C)C1=NC(=C2C(NC(=NN21)C2CCCC2)=O)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:21]1[n:10][n:11][c:12]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17]2)[nH:18][c:19]1=[O:20])[C:6]([CH3:7])([CH3:8])[CH3:9]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([C:6]([CH3:7])([CH3:8])[CH3:9])[n:10]2[n:11][c:12]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[nH:18][c:19](=[O:20])[c:21]12 | CCC(NC(=O)C(C)(C)C)c1nnc(C2CCCC2)[nH]c1=O | CCc1nc(C(C)(C)C)n2nc(C3CCCC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CCCC2)nn2cncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16]>>[C;D1;H3:5]-[C:4]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:1](-[C:13](-[C;D1;H3:14])(-[C;D1;H3:15])-[C;D1;H3:16]):[n;H0;D3;+0:7]2:[#7... | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 200 mg (0.65 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]-2,2-dimethylpropanamide, 165 mg (1.1 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The product is purified by chromatogra... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | c1ncc2cncn2n1.C1CCCC1 | HO- | null | null | null | CCC(NC(=O)C(C)(C)C)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C(C)(C)C)n2nc(C3CCCC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5e11825c5d714cc6bbd7a0edf51373e8 | CCC(NC(=O)CC1CCCCC1)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(CC2CCCCC2)n2nc(C3CCCC3)[nH]c(=O)c12 | C1(CCCCC1)CC(=O)NC(CC)C=1C(NC(=NN1)C1CCCC1)=O.P(=O)(Cl)(Cl)Cl>>C1(CCCCC1)CC1=NC(=C2C(NC(=NN21)C2CCCC2)=O)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:24]1[n:13][n:14][c:15]([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[nH:21][c:22]1=[O:23])[CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH2:6][CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[n:13]2[n:14][c:15]([CH:16]3[CH2:17][CH2:18][CH2:19][C... | CCC(NC(=O)CC1CCCCC1)c1nnc(C2CCCC2)[nH]c1=O | CCc1nc(CC2CCCCC2)n2nc(C3CCCC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CCCC2)nn2c(CC3CCCCC3)ncc12 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[NH;D2;+0:4]-[CH;D3;+0:5](-[C:6]-[C;D1;H3:7])-[c:8]1:[n;H0;D2;+0:9]:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:1=[O;D1;H0:14]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[c;H0;D3;+0:5](-[C:6]-[C;D1;H3:7]):[c:8]2:[c:13](=[O;D1;H0:14]):[#7;a:12]:[c:11]:[#7;a:10]:[n;H0;D3;+0:9]:2:1 | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 200 mg (0.52 mmol) crude 2-cyclohexyl-N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]acetamide, 165 mg (1.1 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The product is purified by chromatograph... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CCCCC1.c1ncc2cncn2n1.C1CCCC1 | HO- | null | null | null | CCC(NC(=O)CC1CCCCC1)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(CC2CCCCC2)n2nc(C3CCCC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a82801fa99d41adaee3aaed40ff324b | CCCCC(CC)C(=O)NC(CC)c1nnc(C2CCCC2)[nH]c1=O>>CCCCC(CC)c1nc(CC)c2c(=O)[nH]c(C3CCCC3)nn12 | C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(C(CCCC)CC)=O.P(=O)(Cl)(Cl)Cl>>C1(CCCC1)C1=NN2C(C(N1)=O)=C(N=C2C(CCCC)CC)CC | O=[C:8]([CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH3:7])[NH:9][CH:10]([CH2:11][CH3:12])[c:13]1[c:14](=[O:15])[nH:16][c:17]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[n:23][n:24]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[c:8]1[n:9][c:10]([CH2:11][CH3:12])[c:13]2[c:14](=[O:15])[nH:16][c:17]([CH:18]3[CH2:19]... | CCCCC(CC)C(=O)NC(CC)c1nnc(C2CCCC2)[nH]c1=O | CCCCC(CC)c1nc(CC)c2c(=O)[nH]c(C3CCCC3)nn12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CCCC2)nn2cncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9](-[C:10]):[#7;a:11]:[c:12]:1=[O;D1;H0:13])-[C:14](-[C:15])-[C:16]>>[C:10]-[c:9]1:[#7;a:11]:[c:12](=[O;D1;H0:13]):[c:6]2:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[n;H0;D2;+0:2]:[c;H0;D3;+0:1](-[C:14](-[C:15])-[C:16]):[n;H0;D3;+... | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 190 mg (0.55 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]-2-ethylhexanamide, 165 mg (1.1 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The product is purified by chromatography (p... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | c1ncc2cncn2n1.C1CCCC1 | HO- | null | null | null | CCCCC(CC)C(=O)NC(CC)c1nnc(C2CCCC2)[nH]c1=O>>CCCCC(CC)c1nc(CC)c2c(=O)[nH]c(C3CCCC3)nn12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a83afc9421604769af37c08c2b3038bc | CCC(NC(=O)C(C)(C)CC)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C(C)(C)CC)n2nc(C3CCCC3)[nH]c(=O)c12 | C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(C(CC)(C)C)=O.P(=O)(Cl)(Cl)Cl>>C1(CCCC1)C1=NN2C(C(N1)=O)=C(N=C2C(C)(C)CC)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:22]1[n:11][n:12][c:13]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18]2)[nH:19][c:20]1=[O:21])[C:6]([CH3:7])([CH3:8])[CH2:9][CH3:10]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([C:6]([CH3:7])([CH3:8])[CH2:9][CH3:10])[n:11]2[n:12][c:13]([CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)[nH:19][c:20](=[O:21])... | CCC(NC(=O)C(C)(C)CC)c1nnc(C2CCCC2)[nH]c1=O | CCc1nc(C(C)(C)CC)n2nc(C3CCCC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=c1[nH]c(C2CCCC2)nn2cncc12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C:14])(-[C;D1;H3:15])-[C;D1;H3:16]>>[C:14]-[C:13](-[C;D1;H3:15])(-[C;D1;H3:16])-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#... | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 211 mg (0.66 mmol) crude N-[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]-2,2-dimethylbutanamide, 165 mg (1.1 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The product is purified by chromatograp... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | c1ncc2cncn2n1.C1CCCC1 | HO- | null | null | null | CCC(NC(=O)C(C)(C)CC)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C(C)(C)CC)n2nc(C3CCCC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ce06e1276c0a4ff28619deb78bf9e8ac | CCC(NC(=O)C1CCN(C(=O)OCc2ccccc2)CC1)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2CCN(C(=O)OCc3ccccc3)CC2)n2nc(C3CCCC3)[nH]c(=O)c12 | C1(CCCC1)C1=NN=C(C(N1)=O)C(CC)NC(=O)C1CCN(CC1)C(=O)OCC1=CC=CC=C1.P(=O)(Cl)(Cl)Cl>>C1(CCCC1)C1=NN2C(C(N1)=O)=C(N=C2C2CCN(CC2)C(=O)OCC2=CC=CC=C2)CC | O=[C:5]([NH:4][CH:3]([CH2:2][CH3:1])[c:33]1[n:22][n:23][c:24]([CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[nH:30][c:31]1=[O:32])[CH:6]1[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[O... | CCC(NC(=O)C1CCN(C(=O)OCc2ccccc2)CC1)c1nnc(C2CCCC2)[nH]c1=O | CCc1nc(C2CCN(C(=O)OCc3ccccc3)CC2)n2nc(C3CCCC3)[nH]c(=O)c12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 3c5d83dfcd7109f683218f4a2fbc6318a6967949b1a10b0e61cecdd6812a48d3 | 4c49decc0d3b49884847872e93a9c81862e00fd5fd04c96a796b9efc98b43f78 | O=C(OCc1ccccc1)N1CCC(c2ncc3c(=O)[nH]c(C4CCCC4)nn23)CC1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[CH;D3;+0:3](-[C:4]-[C;D1;H3:5])-[c:6]1:[n;H0;D2;+0:7]:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1=[O;D1;H0:12])-[C:13](-[C:14])-[C:15]>>[C:14]-[C:13](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:3](-[C:4]-[C;D1;H3:5]):[c:6]2:[c:11](=[O;D1;H0:12]):[#7;a:10]:[c:9]:[#7;a:8]:[n;H0;D3;+0:7]:2:1)-[C:15] | null | [] | null | null | null | null | In analogy to the procedure for Example 1, 500 mg (1.07 mmol) crude benzyl 4-({[1-(3-cyclopentyl-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl)propyl]amino}carbonyl)-1-piperidinecarboxylate, 248 mg (1.7 mmol) phosphoric trichloride are stirred at reflux for 4 hours, proportionate amounts of the solvents are used. The product is... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | c1cnncn1 | c1ncc2cncn2n1 | C1CC[NH]CC1.c1ccccc1.c1ncc2cncn2n1.C1CCCC1 | HO- | null | null | null | CCC(NC(=O)C1CCN(C(=O)OCc2ccccc2)CC1)c1nnc(C2CCCC2)[nH]c1=O>>CCc1nc(C2CCN(C(=O)OCc3ccccc3)CC2)n2nc(C3CCCC3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-68fa38bc4e1d4b57ae1257ff098cfd25 | CCc1nc(C2CCNCC2)n2nc(-c3ccccc3)[nH]c(=O)c12.O=C(Cl)C1CCCC1>>CCc1nc(C2CCN(C(=O)C3CCCC3)CC2)n2nc(-c3ccccc3)[nH]c(=O)c12 | C(C)C=1N=C(N2N=C(NC(C21)=O)C2=CC=CC=C2)C2CCNCC2.C1(CCCC1)C(=O)Cl>>C1(CCCC1)C(=O)N1CCC(CC1)C1=NC(=C2C(NC(=NN21)C2=CC=CC=C2)=O)CC | [CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][NH:9][CH2:17][CH2:18]2)[n:19]2[n:20][c:21](-[c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[nH:28][c:29](=[O:30])[c:31]12.Cl[C:10](=[O:11])[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[CH:12]3[CH2:13... | CCc1nc(C2CCNCC2)n2nc(-c3ccccc3)[nH]c(=O)c12.O=C(Cl)C1CCCC1 | CCc1nc(C2CCN(C(=O)C3CCCC3)CC2)n2nc(-c3ccccc3)[nH]c(=O)c12 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | aaa7c80569e6aa145ac8d7318e06893ee71aff0c965e85eca836522c948938d5 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(C1CCCC1)N1CCC(c2ncc3c(=O)[nH]c(-c4ccccc4)nn23)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8](-[C:7]-[C:6])-[C:9]-[C:10])-[C:5] | null | [] | null | null | null | null | In analogy to the procedure for Example 103 Step (b), 30 mg (0.09 mmol) 5-ethyl-2-phenyl-7-(4-piperidinyl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one, 14 mg (0.10 mmol) cyclopentanecarbonyl chloride are stirred at room temperature overnight, proportionate amounts of the solvents are used.
Conditions: See reaction.notes.proc... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.C1CCCC1.c1ncc2cncn2n1.c1ccccc1 | HCl | null | null | null | CCc1nc(C2CCNCC2)n2nc(-c3ccccc3)[nH]c(=O)c12.O=C(Cl)C1CCCC1>>CCc1nc(C2CCN(C(=O)C3CCCC3)CC2)n2nc(-c3ccccc3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c29c2191c2d443639bf07ca2ce43a00d | CCc1nc(C2CCNCC2)n2nc(-c3ccccc3)[nH]c(=O)c12.O=C(Cl)c1ccccc1>>CCc1nc(C2CCN(C(=O)c3ccccc3)CC2)n2nc(-c3ccccc3)[nH]c(=O)c12 | C(C)C=1N=C(N2N=C(NC(C21)=O)C2=CC=CC=C2)C2CCNCC2.C(C1=CC=CC=C1)(=O)Cl>>C(C1=CC=CC=C1)(=O)N1CCC(CC1)C1=NC(=C2C(NC(=NN21)C2=CC=CC=C2)=O)CC | [CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][NH:9][CH2:18][CH2:19]2)[n:20]2[n:21][c:22](-[c:23]3[cH:24][cH:25][cH:26][cH:27][cH:28]3)[nH:29][c:30](=[O:31])[c:32]12.Cl[C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][CH2:2][c:3]1[n:4][c:5]([CH:6]2[CH2:7][CH2:8][N:9]([C:10](=[O:11])[c:12]3[cH:13... | CCc1nc(C2CCNCC2)n2nc(-c3ccccc3)[nH]c(=O)c12.O=C(Cl)c1ccccc1 | CCc1nc(C2CCN(C(=O)c3ccccc3)CC2)n2nc(-c3ccccc3)[nH]c(=O)c12 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | aaa7c80569e6aa145ac8d7318e06893ee71aff0c965e85eca836522c948938d5 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(c1ccccc1)N1CCC(c2ncc3c(=O)[nH]c(-c4ccccc4)nn23)CC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]>>[C:6]-[C:7]-[N;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9]-[C:10] | null | [] | null | null | null | null | In analogy to the procedure for Example 103 Step (b), 30 mg (0.09 mmol) 5-ethyl-2-phenyl-7-(4-piperidinyl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one, 14 mg (0.10 mmol) benzoyl chloride are stirred at room temperature overnight, proportionate amounts of the solvents are used.
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccccc1.c1ncc2cncn2n1.c1ccccc1 | HCl | null | null | null | CCc1nc(C2CCNCC2)n2nc(-c3ccccc3)[nH]c(=O)c12.O=C(Cl)c1ccccc1>>CCc1nc(C2CCN(C(=O)c3ccccc3)CC2)n2nc(-c3ccccc3)[nH]c(=O)c12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0a309e52be4b46568b3b57cb491326c7 | C[C@H](NC(=O)OC(C)(C)C)c1cccc(Br)c1.c1ccc(N2CCNCC2)nc1>>C[C@H](NC(=O)OC(C)(C)C)c1cccc(N2CCN(c3ccccn3)CC2)c1 | C(C)(C)(C)OC(N[C@@H](C)C1=CC(=CC=C1)Br)=O.N1=C(C=CC=C1)N1CCNCC1.P(=O)([O-])([O-])[O-].[K+].[K+].[K+]>>C(C)(C)(C)OC(N[C@@H](C)C1=CC(=CC=C1)N1CCN(CC1)C1=NC=CC=C1)=O | Br[c:15]1[cH:14][cH:13][cH:12][c:11]([C@H:2]([CH3:1])[NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[cH:28]1.[NH:16]1[CH2:17][CH2:18][N:19]([c:20]2[cH:21][cH:22][cH:23][cH:24][n:25]2)[CH2:26][CH2:27]1>>[CH3:1][C@H:2]([NH:3][C:4](=[O:5])[O:6][C:7]([CH3:8])([CH3:9])[CH3:10])[c:11]1[cH:12][cH:13][cH:14][c:15]([N:... | C[C@H](NC(=O)OC(C)(C)C)c1cccc(Br)c1.c1ccc(N2CCNCC2)nc1 | C[C@H](NC(=O)OC(C)(C)C)c1cccc(N2CCN(c3ccccn3)CC2)c1 | 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] | ClCCl.COCCOC | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 75de53007ec0cb91435746fdefbf3b121f745fc71ddebd19c6e45a5212b3f56a | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCN(c3ccccn3)CC2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:5]:[c:4]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#7:6]-[C:11]-[C:10]-1):[c:2]:[c:3] | 64.2 | [{"value": 64.0, "product": "C(C)(C)(C)OC(N[C@@H](C)C1=CC(=CC=C1)N1CCN(CC1)C1=NC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.2, "product": "C(C)(C)(C)OC(N[C@@H](C)C1=CC(=CC=C1)N1CCN(CC1)C1=NC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of (S)-[1-(3-bromophenyl)ethyl]carbamic acid tert-butyl ester (5.0 g, 16.7 mmol), 1-pyridin-2-ylpiperazine (10.9 g, 67 mmol), Pd2(dba)3 (1.55 g, 10 mol %), di-t-butyl-biphenylphosphine (0.51 g, 10 mol %), potassium phosphate (7.2 g, 34 mmol) in ethyleneglycol dimethyl ether (40 mL) was refluxed for 4 h. After... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1ccccc1.C1CNCC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | 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].ClCCl.COCCOC | null | null | C[C@H](NC(=O)OC(C)(C)C)c1cccc(Br)c1.c1ccc(N2CCNCC2)nc1>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].ClCCl.COCCOC>C[C@H](NC(=O)OC(C)(C)C)c1cccc(N2CCN(c3ccccn3)CC2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-96a4cec411f14a0684b762b320f4b158 | C[C@H](NC(=O)OC(C)(C)C)c1cccc(N2CCN(c3ccccn3)CC2)c1>>C[C@H](N)c1cccc(N2CCN(c3ccccn3)CC2)c1 | C(C)(C)(C)OC(N[C@@H](C)C1=CC(=CC=C1)N1CCN(CC1)C1=NC=CC=C1)=O.Cl>>N1=C(C=CC=C1)N1CCN(CC1)C=1C=C(C=CC1)[C@H](C)N | CC(C)(C)OC(=O)[NH:3][C@@H:2]([CH3:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][N:12]([c:13]3[cH:14][cH:15][cH:16][cH:17][n:18]3)[CH2:19][CH2:20]2)[cH:21]1>>[CH3:1][C@H:2]([NH2:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][N:12]([c:13]3[cH:14][cH:15][cH:16][cH:17][n:18]3)[CH2:19][CH2:20]2)[cH:21]1 | C[C@H](NC(=O)OC(C)(C)C)c1cccc(N2CCN(c3ccccn3)CC2)c1 | C[C@H](N)c1cccc(N2CCN(c3ccccn3)CC2)c1 | null | null | O1CCOCC1 | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(N2CCN(c3ccccn3)CC2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C;D1;H3:3])-[c:4]>>[C;D1;H3:3]-[C:2](-[NH2;D1;+0:1])-[c:4] | 89.4 | [{"value": 89.0, "product": "N1=C(C=CC=C1)N1CCN(CC1)C=1C=C(C=CC1)[C@H](C)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.4, "product": "N1=C(C=CC=C1)N1CCN(CC1)C=1C=C(C=CC1)[C@H](C)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (S)-{1-[3-(4-pyridin-2-ylpiperazin-1-yl)phenyl]ethyl}carbamic acid tert-butyl ester (4.1 g, 10.7 mmol) and hydrochloric acid (4N, 11 mL) in dioxane (40 mL) was stirred at 40° C. for 5 h. The reaction mixture was concentrated under vacuum, dissolved into water (50 mL), and washed with dichloromethane (2×50... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HO- | O1CCOCC1 | null | null | C[C@H](NC(=O)OC(C)(C)C)c1cccc(N2CCN(c3ccccn3)CC2)c1>O1CCOCC1>C[C@H](N)c1cccc(N2CCN(c3ccccn3)CC2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e9942dd2878d4dca917c28cc1fed1a55 | C[C@H](N)c1cccc(N2CCN(c3ccccn3)CC2)c1.O=C(O)C=Cc1ccc(F)cc1>>C[C@H](NC(=O)C=Cc1ccc(F)cc1)c1cccc(N2CCN(c3ccccn3)CC2)c1 | FC1=CC=C(C=CC(=O)O)C=C1.N1=C(C=CC=C1)N1CCN(CC1)C=1C=C(C=CC1)[C@H](C)N.C(CCl)Cl.C(C)N(CC)CC>>FC1=CC=C(C=C1)C=CC(=O)N[C@@H](C)C1=CC(=CC=C1)N1CCN(CC1)C1=NC=CC=C1 | [CH3:1][C@H:2]([NH2:3])[c:15]1[cH:16][cH:17][cH:18][c:19]([N:20]2[CH2:21][CH2:22][N:23]([c:24]3[cH:25][cH:26][cH:27][cH:28][n:29]3)[CH2:30][CH2:31]2)[cH:32]1.O[C:4](=[O:5])[CH:6]=[CH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1>>[CH3:1][C@H:2]([NH:3][C:4](=[O:5])[CH:6]=[CH:7][c:8]1[cH:9][cH:10][c:11]([F:12])[cH:1... | C[C@H](N)c1cccc(N2CCN(c3ccccn3)CC2)c1.O=C(O)C=Cc1ccc(F)cc1 | C[C@H](NC(=O)C=Cc1ccc(F)cc1)c1cccc(N2CCN(c3ccccn3)CC2)c1 | null | CN(C)C=1C=CN=CC1 | ClCCl | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(C=Cc1ccccc1)NCc1cccc(N2CCN(c3ccccn3)CC2)c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5].[C;D1;H3:6]-[C:7](-[NH2;D1;+0:8])-[c:9]>>[C;D1;H3:6]-[C:7](-[c:9])-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]=[C:4]-[c:5] | 60.4 | [{"value": 60.0, "product": "FC1=CC=C(C=C1)C=CC(=O)N[C@@H](C)C1=CC(=CC=C1)N1CCN(CC1)C1=NC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.4, "product": "FC1=CC=C(C=C1)C=CC(=O)N[C@@H](C)C1=CC(=CC=C1)N1CCN(CC1)C1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 4-fluorocinnamic acid (17 mg, 0.1 mmol), (S)-1-[3-(4-pyridin-2-yl-piperazin-1-yl)phenyl]ethylamine (24 mg, 0.11 mmol), EDC (28 mg, 0.15 mmol), DMAP (12 mg, 0.1 mmol) and triethylamine (40 mg, 0.4 mmol) in dichloromethane (2 ml) was stirred at room temperature for 14 h. The reaction mixture was purified by... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1.c1ccncc1 | HO- | CN(C)C=1C=CN=CC1.ClCCl | null | null | C[C@H](N)c1cccc(N2CCN(c3ccccn3)CC2)c1.O=C(O)C=Cc1ccc(F)cc1>CN(C)C=1C=CN=CC1.ClCCl>C[C@H](NC(=O)C=Cc1ccc(F)cc1)c1cccc(N2CCN(c3ccccn3)CC2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c4d7fad97933430f899237cc4fde1812 | O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1>>O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1 | Cl.S1N=C(C2=C1C=CC=C2)N2CCN(CC2)CCC=2C=C1CC(NC1=CC2Cl)=O.C(C)O>>Cl.S1N=C(C2=C1C=CC=C2)N2CCN(CC2)CCC=2C=C1CC(NC1=CC2Cl)=O | [O:2]=[C:3]1[CH2:4][c:5]2[cH:6][c:7]([CH2:8][CH2:9][N:10]3[CH2:11][CH2:12][N:13]([c:14]4[n:15][s:16][c:17]5[cH:18][cH:19][cH:20][cH:21][c:22]45)[CH2:23][CH2:24]3)[c:25]([Cl:26])[cH:27][c:28]2[NH:29]1>>[O:2]=[C:3]1[CH2:4][c:5]2[cH:6][c:7]([CH2:8][CH2:9][N:10]3[CH2:11][CH2:12][N:13]([c:14]4[n:15][s:16][c:17]5[cH:18][cH:1... | O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1 | O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1 | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)ccc2N1 | null | null | [] | null | null | 24 | HOUR | To a flask equipped with magnetic stirrer, thermometer and nitrogen inlet was added 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one free base (5.0 g) and ethanol (100 mL) and the suspension was stirred at 20–25° C. under nitrogen. A 20.5% anhydrous solution of hydrogen chlorid... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)CCN2.C1C[NH]CC[NH]1.c1ccc2sncc2c1 | null | C(C)(C)O | null | 24 | O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1>C(C)(C)O>O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e370f8717366441a979d1a10c6ae373a | O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1>>O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1 | Cl.S1N=C(C2=C1C=CC=C2)N2CCN(CC2)CCC=2C=C1CC(NC1=CC2Cl)=O.C(C(C)C)C(=O)C>>Cl.S1N=C(C2=C1C=CC=C2)N2CCN(CC2)CCC=2C=C1CC(NC1=CC2Cl)=O | [O:2]=[C:3]1[CH2:4][c:5]2[cH:6][c:7]([CH2:8][CH2:9][N:10]3[CH2:11][CH2:12][N:13]([c:14]4[n:15][s:16][c:17]5[cH:18][cH:19][cH:20][cH:21][c:22]45)[CH2:23][CH2:24]3)[c:25]([Cl:26])[cH:27][c:28]2[NH:29]1>>[O:2]=[C:3]1[CH2:4][c:5]2[cH:6][c:7]([CH2:8][CH2:9][N:10]3[CH2:11][CH2:12][N:13]([c:14]4[n:15][s:16][c:17]5[cH:18][cH:1... | O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1 | O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1 | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)ccc2N1 | null | null | [] | null | null | null | null | To a flask equipped with magnetic stirrer, thermometer and nitrogen inlet was added 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one free base (5.0 g) and methyl isobutyl ketone (100 mL) and the suspension was stirred at 20–25° C. under nitrogen. A 20.5% anhydrous solution of h... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)CCN2.C1C[NH]CC[NH]1.c1ccc2sncc2c1 | null | C(C)(C)O | null | null | O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1>C(C)(C)O>O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d6f3e0d7fddb4fc9a434ada79b3951cc | O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1>>O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1 | Cl.S1N=C(C2=C1C=CC=C2)N2CCN(CC2)CCC=2C=C1CC(NC1=CC2Cl)=O.CN1C(CCC1)=O>>Cl.S1N=C(C2=C1C=CC=C2)N2CCN(CC2)CCC=2C=C1CC(NC1=CC2Cl)=O | [O:2]=[C:3]1[CH2:4][c:5]2[cH:6][c:7]([CH2:8][CH2:9][N:10]3[CH2:11][CH2:12][N:13]([c:14]4[n:15][s:16][c:17]5[cH:18][cH:19][cH:20][cH:21][c:22]45)[CH2:23][CH2:24]3)[c:25]([Cl:26])[cH:27][c:28]2[NH:29]1>>[O:2]=[C:3]1[CH2:4][c:5]2[cH:6][c:7]([CH2:8][CH2:9][N:10]3[CH2:11][CH2:12][N:13]([c:14]4[n:15][s:16][c:17]5[cH:18][cH:1... | O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1 | O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1 | null | null | C(C)(C)O | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)ccc2N1 | null | null | [] | 25 | CELSIUS | 3 | HOUR | To a 3-necked flask equipped with mechanical stirrer, thermometer and nitrogen inlet was added 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one free base (5.0 g) and 1-methyl-2-pyrrolidinone (60 mL) under nitrogen and the suspension was warmed up to 35–40° C. to dissolution. Th... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccc2c(c1)CCN2.C1C[NH]CC[NH]1.c1ccc2sncc2c1 | null | C(C)(C)O | 25 | 3 | O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1>C(C)(C)O>O=C1Cc2cc(CCN3CCN(c4nsc5ccccc45)CC3)c(Cl)cc2N1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4a0df95c9b4b498e9f87abb23dd872c0 | C[C@@H]1CN(C(=O)c2ccccc2)CCN1.N#CCC(=O)O>>C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)CC#N | C1CCC(CC1)N=C=NC2CCCCC2.C(C)N(CC)CC.C(#N)CC(=O)O.C(C1=CC=CC=C1)(=O)N1C[C@H](NCC1)C>>C(C1=CC=CC=C1)(=O)N1C[C@H](N(CC1)C(CC#N)=O)C | [CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][NH:15]1.O[C:16](=[O:17])[CH2:18][C:19]#[N:20]>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][N:15]1[C:16](=[O:17])[CH2:18][C:19]#[N:20] | C[C@@H]1CN(C(=O)c2ccccc2)CCN1.N#CCC(=O)O | C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)CC#N | null | null | C1CCOC1 | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ed26ef5eea92a0cc433b3f89a34f4c61724425fa15a9d0ec83a0f7a903eec831 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(c1ccccc1)N1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]#[N;D1;H0:5].[C;D1;H3:6]-[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[NH;D2;+0:12]-1>>[C;D1;H3:6]-[C:7]1-[C:8]-[#7:9]-[C:10]-[C:11]-[N;H0;D3;+0:12]-1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]#[N;D1;H0:5] | 94.1 | [{"value": 94.1, "product": "C(C1=CC=CC=C1)(=O)N1C[C@H](N(CC1)C(CC#N)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 12 | HOUR | DCC (2.43 g) and triethylamine (5 ml) were added into a solution of cyanoacetic acid (1.00 g) and (R)-N-benzoyl-3-methylpiperazine (2.84 g) in THF (50 ml). After reaction stirred at room temperature for 12 hours, solvents were removed under vacuum to give a residue which was purified by silica gel column chromatography... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | HO- | C1CCOC1 | null | 12 | C[C@@H]1CN(C(=O)c2ccccc2)CCN1.N#CCC(=O)O>C1CCOC1>C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)CC#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f3be17d383a14b1f9a00d9ceecf8569f | N#CCCl.c1ccc(CN2CCNCC2)cc1>>N#CCN1CCN(Cc2ccccc2)CC1 | ClCC#N.C(C1=CC=CC=C1)N1CCNCC1>>C(C1=CC=CC=C1)N1CCN(CC1)CC#N | Cl[CH2:3][C:2]#[N:1].[NH:4]1[CH2:5][CH2:6][N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][CH2:16]1>>[N:1]#[C:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][CH2:16]1 | N#CCCl.c1ccc(CN2CCNCC2)cc1 | N#CCN1CCN(Cc2ccccc2)CC1 | null | null | C1CCOC1.CCN(CC)CC | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | bad6b7d8e43c3debef0c262d60564e43415b41bcee72e526419c8c16be18fec1 | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2CCNCC2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].[#7:4]1-[C:5]-[C:6]-[NH;D2;+0:7]-[C:8]-[C:9]-1>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:7]1-[C:6]-[C:5]-[#7:4]-[C:9]-[C:8]-1 | null | [] | null | null | 10 | HOUR | An excess of chloroacetonitrile (7 ml) was added in to a solution of benzylpiperazine (2 g, 10.5 mmol) in THF (100 ml) and Et3N (10 ml). The reaction was stirred for 10 hours before quenched with saturated aqueous NaHCO3 (100 ml). The aqueous phase was extracted with EtOAc (3×100 ml). The combined organic layer was dri... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1ccccc1 | HCl | C1CCOC1.CCN(CC)CC | null | 10 | N#CCCl.c1ccc(CN2CCNCC2)cc1>C1CCOC1.CCN(CC)CC>N#CCN1CCN(Cc2ccccc2)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a40547b8595849ebabaf584db239ee95 | C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)CC#N.Clc1nc2ccccc2s1>>C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(C#N)c1nc2ccccc2s1 | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].C(C1=CC=CC=C1)(=O)N1C[C@H](N(CC1)C(CC#N)=O)C.ClC=1SC2=C(N1)C=CC=C2>>C(C1=CC=CC=C1)(=O)N1C[C@H](N(CC1)C(C(C#N)C=1SC2=C(N1)C=CC=C2)=O)C | [CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][N:15]1[C:16](=[O:17])[CH2:18][C:19]#[N:20].Cl[c:21]1[n:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[s:29]1>>[CH3:1][C@@H:2]1[CH2:3][N:4]([C:5](=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14][N:15]1[C:16... | C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)CC#N.Clc1nc2ccccc2s1 | C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(C#N)c1nc2ccccc2s1 | null | null | C1CCOC1 | C-C Coupling | Hurtley reaction | 3c9e7a1a189a138f95a7b064041471166aeb1d19ae8fac18b63c3a9fc024ed1a | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | O=C(Cc1nc2ccccc2s1)N1CCN(C(=O)c2ccccc2)CC1 | Cl-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1.[C:6]-[#7:7](-[C:8](=[O;D1;H0:9])-[CH2;D2;+0:10]-[C:11]#[N;D1;H0:12])-[C:13]>>[C:6]-[#7:7](-[C:8](=[O;D1;H0:9])-[CH;D3;+0:10](-[C:11]#[N;D1;H0:12])-[c;H0;D3;+0:1]1:[#16;a:2]:[c:3]:[c:4]:[#7;a:5]:1)-[C:13] | 6.5 | [{"value": 6.5, "product": "C(C1=CC=CC=C1)(=O)N1C[C@H](N(CC1)C(C(C#N)C=1SC2=C(N1)C=CC=C2)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | HOUR | NaHMDS (1.48 ml, 1M in THF) was added into a solution of (R)-N-benzoyl-3-methyl-N′-(2-cyano-acetyl)piperazine (190 mg) and 2-chlorobenzothiazole (100 mg) in THF (10 ml). After the reaction was stirred for 10 hours, 4 ml of solution was separated and quenched with MeOH. After solvents were removed under vaccum, the resi... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccc2scnc2c1 | c1ccc2scnc2c1 | C1C[NH]CC[NH]1.c1ccccc1.c1ccc2scnc2c1 | HCl | C1CCOC1 | null | 10 | C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)CC#N.Clc1nc2ccccc2s1>C1CCOC1>C[C@@H]1CN(C(=O)c2ccccc2)CCN1C(=O)C(C#N)c1nc2ccccc2s1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-28046646c1654096b7755cc2c17642b7 | COc1ccc2sc(C#N)nc2c1.C[C@@H]1CN(Cc2ccccc2)CCN1CC#N>>COc1ccc2sc(C(=N)C(C#N)N3CCN(C(=O)c4ccccc4)C[C@H]3C)nc2c1 | C[Si](C)(C)[N-][Si](C)(C)C.[Na+].C(C1=CC=CC=C1)N1C[C@H](N(CC1)CC#N)C.C(#N)C=1SC2=C(N1)C=C(C=C2)OC.C1CCOC1>>C(C1=CC=CC=C1)(=O)N1C[C@H](N(CC1)C(C(=N)C=1SC2=C(N1)C=C(C=C2)OC)C#N)C | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[s:7][c:8]([C:9]#[N:10])[n:29][c:30]2[cH:31]1.[CH2:11]([C:12]#[N:13])[N:14]1[CH2:15][CH2:16][N:17]([CH2:18][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[CH2:26][C@H:27]1[CH3:28]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[s:7][c:8]([C:9](=[NH:10])[CH:11]([C:12]#[N:13])[N:14]3[CH2:15][CH2:16... | COc1ccc2sc(C#N)nc2c1.C[C@@H]1CN(Cc2ccccc2)CCN1CC#N | COc1ccc2sc(C(=N)C(C#N)N3CCN(C(=O)c4ccccc4)C[C@H]3C)nc2c1 | null | null | null | Functional Group Addition | OtherReaction | 704c254f7108b9db063307266438a3254b69ff156320c90b571729d32dfaddc2 | bbd379aa3a1ece083eed0667216ada44ce75929e7d5e2fa212010da588832082 | N=C(CN1CCN(C(=O)c2ccccc2)CC1)c1nc2ccccc2s1 | [N;D1;H0:1]#[C:2]-[CH2;D2;+0:3]-[#7:4]1-[C:5]-[C:6]-[#7:7](-[CH2;D2;+0:8]-[c:9](:[c:10]):[c:11])-[C:12]-[C:13]-1.[N;H0;D1;+0:14]#[C;H0;D2;+0:15]-[c:16]1:[#16;a:17]:[c:18]:[c:19]:[#7;a:20]:1>>[N;D1;H0:1]#[C:2]-[CH;D3;+0:3](-[#7:4]1-[C:5]-[C:6]-[#7:7](-[C;H0;D3;+0:8](=[O;D1;H0:21])-[c:9](:[c:10]):[c:11])-[C:12]-[C:13]-1)... | null | [] | null | null | 10 | HOUR | NaHMDS (0.77 ml, 1M in THF) was added into a solution of (R)-N-benzyl-3-methyl-N′-cyanomethylpiperazine (100 mg) and 2-cyano-5-methoxy-benzothiazole (58 mg) in THF (10 ml). The reaction was stirred for 10 hours. Then 4 ml of the reaction mixture was separated and quenched with MeOH. After solvents were removed under va... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Unsubstituted imine.Tertiary amide | null | null | c1ccc2scnc2c1.C1C[NH]CC[NH]1.c1ccccc1 | Other | null | null | 10 | COc1ccc2sc(C#N)nc2c1.C[C@@H]1CN(Cc2ccccc2)CCN1CC#N>>COc1ccc2sc(C(=N)C(C#N)N3CCN(C(=O)c4ccccc4)C[C@H]3C)nc2c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-40d7272e26be49c1ab66795f224e7323 | Cc1cc(N)n[nH]1.Clc1nc(Cl)c2ccccc2n1>>Cc1cc(Nc2nc(Cl)nc3ccccc23)[nH]n1 | ClC1=NC2=CC=CC=C2C(=N1)Cl.NC1=NNC(=C1)C.C(C)N(CC)CC>>ClC1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C | [CH3:1][c:2]1[cH:3][c:4]([NH2:5])[n:17][nH:18]1.Cl[c:6]1[n:7][c:8]([Cl:9])[n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][c:8]([Cl:9])[n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]23)[nH:17][n:18]1 | Cc1cc(N)n[nH]1.Clc1nc(Cl)c2ccccc2n1 | Cc1cc(Nc2nc(Cl)nc3ccccc23)[nH]n1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc2c(Nc3ccn[nH]3)ncnc2c1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:1:[c:8].[C;D1;H3:9]-[c:10]1:[c:11]:[c:12](-[NH2;D1;+0:13]):[n;H0;D2;+0:14]:[nH;D2;+0:15]:1>>[C;D1;H3:9]-[c:10]1:[c:11]:[c:12](-[NH;D2;+0:13]-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3]:[#7;a:4]:[c:5](:[c:6]):[c:7]:2:[c:8]):[nH;D2;+0:14]:[n;H0;D2;+0:15]:1 | null | [] | null | null | 3 | HOUR | To a solution of 2,4-dichloroquinazoline (12.69 g, 63 mmol) and 3-amino-5-methylpyrazole (6.18 g, 63 mmol) in ethanol (220 mL) is added triethylamine (8.13 mL, 63 mmol) and the reaction mixture is stirred for 3 hours at room temperature. The pale yellow precipitate is then collected by filtration, washed with cold etha... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1cn[nH]c1.c1ccc2ncncc2c1 | HCl | C(C)O | null | 3 | Cc1cc(N)n[nH]1.Clc1nc(Cl)c2ccccc2n1>C(C)O>Cc1cc(Nc2nc(Cl)nc3ccccc23)[nH]n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-146b3c8e59384016b6cc83684726e02d | Cc1cc(Nc2nc(Cl)nc3ccccc23)[nH]n1.Nc1cccc(Cl)c1>>Cc1cc(Nc2nc(Nc3cccc(Cl)c3)nc3ccccc23)[nH]n1 | ClC1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C.ClC=1C=C(N)C=CC1.C(=O)([O-])[O-].[K+].[K+]>>ClC=1C=C(C=CC1)NC1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C | Cl[c:8]1[n:7][c:6]([NH:5][c:4]2[cH:3][c:2]([CH3:1])[n:25][nH:24]2)[c:23]2[c:18]([n:17]1)[cH:19][cH:20][cH:21][cH:22]2.[NH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([Cl:15])[cH:16]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][cH:13][c:14]([Cl:15])[cH:16]3)[n:17][c:18]3[cH:19][cH:20][cH:21][c... | Cc1cc(Nc2nc(Cl)nc3ccccc23)[nH]n1.Nc1cccc(Cl)c1 | Cc1cc(Nc2nc(Nc3cccc(Cl)c3)nc3ccccc23)[nH]n1 | null | null | C(C)(C)(C)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | 94bd1d6b149f0eabeae34be7987089f25636bc079a6d701a568fe61e8bfdb7f3 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nc(Nc3ccn[nH]3)c3ccccc3n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[NH;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | 2 | HOUR | The above-prepared (2-chloroquinazolin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine (155 mg, 0.6 mmol) and 3-chloroaniline (0.316 mL, 2.99 mmol) are refluxed in tert-butanol (3 mL) over 20 h. The mixture is concentrated in vacuo and the residue is suspended in EtOH/H2O (1 mL/3 mL). K2CO3 (83 mg, 0.6 mmol) is added and the su... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1cn[nH]c1.c1ccccc1.c1ccc2ncncc2c1 | HCl | C(C)(C)(C)O | null | 2 | Cc1cc(Nc2nc(Cl)nc3ccccc23)[nH]n1.Nc1cccc(Cl)c1>C(C)(C)(C)O>Cc1cc(Nc2nc(Nc3cccc(Cl)c3)nc3ccccc23)[nH]n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d9d7db8763554a4e87f3deec5be27ca4 | COc1cccc(O)c1.Cc1cc(Nc2nc(Cl)nc3ccccc23)[nH]n1>>COc1cccc(Oc2nc(Nc3cc(C)n[nH]3)c3ccccc3n2)c1 | C(=O)([O-])[O-].[K+].[K+].ClC1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C.[H-].[Na+].COC=1C=C(C=CC1)O>>COC=1C=C(OC2=NC3=CC=CC=C3C(=N2)NC=2NN=C(C2)C)C=CC1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([OH:8])[cH:26]1.Cl[c:9]1[n:10][c:11]([NH:12][c:13]2[cH:14][c:15]([CH3:16])[n:17][nH:18]2)[c:19]2[cH:20][cH:21][cH:22][cH:23][c:24]2[n:25]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][c:9]2[n:10][c:11]([NH:12][c:13]3[cH:14][c:15]([CH3:16])[n:17][nH:18]3)[c:19]3[cH:20][cH:21... | COc1cccc(O)c1.Cc1cc(Nc2nc(Cl)nc3ccccc23)[nH]n1 | COc1cccc(Oc2nc(Nc3cc(C)n[nH]3)c3ccccc3n2)c1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 2d25b59c80a437134e7830160726da4e12ee4089c37759035843c1cccd8cd262 | 27e9a6bab4e3ed54aeb6be4d84cb1c0170208288795e252a46e57e44ecc064f0 | c1ccc(Oc2nc(Nc3ccn[nH]3)c3ccccc3n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[OH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[O;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | Sodium hydride (45 mg, 1.12 mmol) in THF (2 mL) is treated with 3-methoxyphenol (0.94 g, 7.6 mmol) and the reaction mixture is stirred until effervescence ceases. The THF is removed in vacuo and the above-prepared (2-chloroquinazolin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine (150 mg, 0.51 mmol)) is added. The reaction mix... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | Ether | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1cn[nH]c1.c1ccc2ncncc2c1 | HCl | C1CCOC1 | null | null | COc1cccc(O)c1.Cc1cc(Nc2nc(Cl)nc3ccccc23)[nH]n1>C1CCOC1>COc1cccc(Oc2nc(Nc3cc(C)n[nH]3)c3ccccc3n2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-69a15a6fb04248a0af12b6034489a596 | O=P(Cl)(Cl)Cl.Oc1nc(COc2ccccc2)nc2ccccc12>>Clc1nc(COc2ccccc2)nc2ccccc12 | OC1=NC(=NC2=CC=CC=C12)COC1=CC=CC=C1.C(CC)N(CCC)CCC.P(=O)(Cl)(Cl)Cl>>ClC1=NC(=NC2=CC=CC=C12)COC1=CC=CC=C1 | O=P(Cl)(Cl)[Cl:1].O[c:2]1[n:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12>>[Cl:1][c:2]1[n:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[n:13][c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12 | O=P(Cl)(Cl)Cl.Oc1nc(COc2ccccc2)nc2ccccc12 | Clc1nc(COc2ccccc2)nc2ccccc12 | null | null | null | Functional Group Interconversion | Alcohol to chloride_POCl3_ortho | b0b0f8b7642d018e3b261231985ddd65d16d4d42cce7aa11791e49c826337b90 | e71580a8ffadb7b2717ecd7d68c1d3c0ca161ba5e6a787a49dad5a1359adc993 | c1ccc(OCc2ncc3ccccc3n2)cc1 | Cl-P(-Cl)(=O)-[Cl;H0;D1;+0:1].O-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:2]1:[#7;a:3]:[c:4]:[#7;a:5]:[c:6](:[c:7]):[c:8]:1:[c:9] | null | [] | 110 | CELSIUS | null | null | To a solution of 4-hydroxy-2-phenoxymethylquinazoline (2 g, 7.93 mmol) in phosphorus oxychloride (10 mL) is added tripropylamine (3.02 mL, 15.8 mmol) and the reaction mixture is heated for 30 minutes at 110° C. The excess phosphorus oxychloride is evaporated in vacuo, the residue is poured, on ice cold aqueous NaHCO3 a... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol | Aromatic halide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1ccc2ncncc2c1 | HCl | null | 110 | null | O=P(Cl)(Cl)Cl.Oc1nc(COc2ccccc2)nc2ccccc12>>Clc1nc(COc2ccccc2)nc2ccccc12 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-06f7d8a3f73b417f902ed4bd441db256 | Clc1nc(Nc2cc(C3CC3)n[nH]2)c2ccccc2n1.[Cl][Mg][CH2]c1ccccc1>>c1ccc(Cc2nc(Nc3cc(C4CC4)n[nH]3)c3ccccc3n2)cc1 | ClC1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C1CC1.C(C1=CC=CC=C1)[Mg]Cl>>C(C1=CC=CC=C1)C1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C1CC1 | Cl[c:6]1[n:7][c:8]([NH:9][c:10]2[cH:11][c:12]([CH:13]3[CH2:14][CH2:15]3)[n:16][nH:17]2)[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[n:24]1.[Cl][Mg][CH2:5][c:4]1[cH:3][cH:2][cH:1][cH:26][cH:25]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][c:6]2[n:7][c:8]([NH:9][c:10]3[cH:11][c:12]([CH:13]4[CH2:14][CH2:15]4)[n:16][nH:17]3)[c:18]3[cH... | Clc1nc(Nc2cc(C3CC3)n[nH]2)c2ccccc2n1.[Cl][Mg][CH2]c1ccccc1 | c1ccc(Cc2nc(Nc3cc(C4CC4)n[nH]3)c3ccccc3n2)cc1 | null | Cl[Ni]1([P](CCC[P](C2=CC=CC=C2)1C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)Cl | C1CCOC1 | C-C Coupling | OtherReaction | d6ecf3ef79974fd9139bedce889147b9ef1b5d3ee3cacdf2cabf013649826619 | 7eab41b7d498a9b6e898b07b0e0d9b3528044390091411fce2a435b647d0bc46 | c1ccc(Cc2nc(Nc3cc(C4CC4)n[nH]3)c3ccccc3n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[Cl]-[Mg]-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[CH2;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | 50 | CELSIUS | null | null | To a solution of the above-prepared (2-chloroquinazolin-4-yl)-(5-cyclopropyl-2H-pyrazol-3-yl)-amine (123 mg, 0.43 mmol) in THF (5 mL) is added NiCl2(dppp) (12 mg, 2.1.10−5 mol), followed by 1M benzylmagnesium chloride in THF (2.15 mL, 2.15 mmol). The solution is heated at 50° C. for 20 hours and the reaction mixture is... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Aromatic halide | null | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1cn[nH]c1.C1CC1.c1ccc2ncncc2c1 | Mg | Cl[Ni]1([P](CCC[P](C2=CC=CC=C2)1C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)Cl.C1CCOC1 | 50 | null | Clc1nc(Nc2cc(C3CC3)n[nH]2)c2ccccc2n1.[Cl][Mg][CH2]c1ccccc1>Cl[Ni]1([P](CCC[P](C2=CC=CC=C2)1C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)Cl.C1CCOC1>c1ccc(Cc2nc(Nc3cc(C4CC4)n[nH]3)c3ccccc3n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6aa0dda9a02f442b9c2c4c5c4181c787 | CC(=O)Nc1ccc(S)cc1.Cc1cc(Nc2nc(Cl)nc3ccccc23)[nH]n1>>CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccccc3n2)cc1 | C(=O)([O-])[O-].[K+].[K+].ClC1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C.C(C)(=O)NC1=CC=C(C=C1)S.C(C)OCC>>C(C)(=O)NC1=CC=C(C=C1)SC1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([SH:9])[cH:27][cH:28]1.Cl[c:10]1[n:11][c:12]([NH:13][c:14]2[cH:15][c:16]([CH3:17])[n:18][nH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[n:26]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15][c:16]([CH3:17])[n:18][nH:... | CC(=O)Nc1ccc(S)cc1.Cc1cc(Nc2nc(Cl)nc3ccccc23)[nH]n1 | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccccc3n2)cc1 | null | null | C(C)(C)(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution thiol | 5e00d229141d58da15c5edb422daba05241810760a4d9b6d5f60ada51e455c66 | 97e4acce9b485bd597e518526ab4e9623782b1c9043b6e30dd257d386e3e5b01 | c1ccc(Sc2nc(Nc3ccn[nH]3)c3ccccc3n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[SH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[S;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | 2 | HOUR | A solution of (2-chloroquinazolin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine (200 mg, 0.77 mmol) and 4-acetamidothiophenol (644 mg, 3.85 mmol) is refluxed in tert-butanol (3 mL) over a 20 hour period. Diethylether (10 mL) is added to the mixture and a solid forms that is collected by filtration. This solid is suspended in ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic thiol | Monosulfide | c1ccc2ncncc2c1 | c1ccc2ncncc2c1 | c1ccccc1.c1cn[nH]c1.c1ccc2ncncc2c1 | HCl | C(C)(C)(C)O | null | 2 | CC(=O)Nc1ccc(S)cc1.Cc1cc(Nc2nc(Cl)nc3ccccc23)[nH]n1>C(C)(C)(C)O>CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccccc3n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a28ecc973c654c54922bd5a78d0be79a | Clc1nc(Cl)c2c(n1)CCCC2.Nc1cc(C2CC2)[nH]n1>>Clc1nc2c(c(Nc3cc(C4CC4)n[nH]3)n1)CCCC2 | [I-].[Na+].ClC1=NC=2CCCCC2C(=N1)Cl.NC1=NNC(=C1)C1CC1.C(C)N(CC)CC>>ClC1=NC=2CCCCC2C(=N1)NC=1NN=C(C1)C1CC1 | Cl[c:6]1[c:5]2[c:4]([n:3][c:2]([Cl:1])[n:16]1)[CH2:20][CH2:19][CH2:18][CH2:17]2.[NH2:7][c:8]1[cH:9][c:10]([CH:11]2[CH2:12][CH2:13]2)[nH:14][n:15]1>>[Cl:1][c:2]1[n:3][c:4]2[c:5]([c:6]([NH:7][c:8]3[cH:9][c:10]([CH:11]4[CH2:12][CH2:13]4)[n:14][nH:15]3)[n:16]1)[CH2:17][CH2:18][CH2:19][CH2:20]2 | Clc1nc(Cl)c2c(n1)CCCC2.Nc1cc(C2CC2)[nH]n1 | Clc1nc2c(c(Nc3cc(C4CC4)n[nH]3)n1)CCCC2 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 424e38c2ee3e9837a281fce535f5a1750f1a6e3f8b06b312203fbbefa35881c6 | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1nc2c(c(Nc3cc(C4CC4)n[nH]3)n1)CCCC2 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6](:[c:7]:1-[C:8])-[C:9].[C:10]-[c:11]1:[c:12]:[c:13](-[NH2;D1;+0:14]):[n;H0;D2;+0:15]:[nH;D2;+0:16]:1>>[C:10]-[c:11]1:[c:12]:[c:13](-[NH;D2;+0:14]-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6](:[c:7]:2-[C:8])-[C:9]):[nH;D2;+0:15]:[n;H0;D2;+0:1... | null | [] | 90 | CELSIUS | null | null | To a solution of 2,4-dichloro-5,6,7,8-tetrahydroquinazoline (500 mg, 2.46 mmol) and 3-amino-5-cyclopropylpyrazole (303 mg, 2.46 mmol) in DMF (10 mL) is added triethylamine (0.357 mL, 2.56 mmol) followed by sodium iodide (368 mg, 2.46 mmol) and the reaction mixture is heated at 90° C. for 20 h. The reaction mixture is p... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ncc2c(n1)CCCC2 | c1ncc2c(n1)CCCC2 | c1cn[nH]c1.C1CC1.c1ncc2c(n1)CCCC2 | HCl | CN(C)C=O | 90 | null | Clc1nc(Cl)c2c(n1)CCCC2.Nc1cc(C2CC2)[nH]n1>CN(C)C=O>Clc1nc2c(c(Nc3cc(C4CC4)n[nH]3)n1)CCCC2 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-58b60263863c4d6096ff5d80ea3e1b48 | COC(=O)c1cccc(Sc2nc(Nc3cc(C4CC4)n[nH]3)c3ccccc3n2)c1>>O=C(O)c1cccc(Sc2nc(Nc3cc(C4CC4)n[nH]3)c3ccccc3n2)c1 | C1(CC1)C=1C=C(NN1)NC1=NC(=NC2=CC=CC=C12)SC1=CC(=CC=C1)C(=O)OC.[Li+].[OH-].Cl>>C(=O)(O)C=1C=C(C=CC1)SC1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C1CC1 | C[O:3][C:2](=[O:1])[c:4]1[cH:5][cH:6][cH:7][c:8]([S:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15][c:16]([CH:17]4[CH2:18][CH2:19]4)[n:20][nH:21]3)[c:22]3[cH:23][cH:24][cH:25][cH:26][c:27]3[n:28]2)[cH:29]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][cH:6][cH:7][c:8]([S:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15][c:16]([CH:17]4[CH2:18... | COC(=O)c1cccc(Sc2nc(Nc3cc(C4CC4)n[nH]3)c3ccccc3n2)c1 | O=C(O)c1cccc(Sc2nc(Nc3cc(C4CC4)n[nH]3)c3ccccc3n2)c1 | null | null | C1CCOC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Sc2nc(Nc3cc(C4CC4)n[nH]3)c3ccccc3n2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 20 | HOUR | A solution of (5-cyclopropyl-2H-pyrazol-3-yl)-[2-(3-methoxycarbonylphenylsulfanyl)-quinazolin-4-yl]-amine (110 mg, 0.26 mmol) in a mixture of THF/water (1/1, 10 mL) is treated with 1M LiOH (0.75 mL, 0.75 mmol). The mixture is stirred for 20 hours at room temperature and then neutralized with 1M HCl (0.75 mL, 0.75 mmol)... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1cn[nH]c1.C1CC1.c1ccc2ncncc2c1 | Other | C1CCOC1.O | null | 20 | COC(=O)c1cccc(Sc2nc(Nc3cc(C4CC4)n[nH]3)c3ccccc3n2)c1>C1CCOC1.O>O=C(O)c1cccc(Sc2nc(Nc3cc(C4CC4)n[nH]3)c3ccccc3n2)c1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-28022122e34041bda82b5d3e08f7f1cd | COc1ccc2c(Nc3cc(C)n[nH]3)nc(Sc3ccc(NC(C)=O)cc3)nc2c1>>CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccc(O)cc3n2)cc1 | C(C)(=O)NC1=CC=C(C=C1)SC1=NC2=CC(=CC=C2C(=N1)NC=1NN=C(C1)C)OC.B(Br)(Br)Br.B(Br)(Br)Br>>C(C)(=O)NC1=CC=C(C=C1)SC1=NC2=CC(=CC=C2C(=N1)NC=1NN=C(C1)C)O | C[O:24][c:23]1[cH:22][cH:21][c:20]2[c:12]([NH:13][c:14]3[cH:15][c:16]([CH3:17])[n:18][nH:19]3)[n:11][c:10]([S:9][c:8]3[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:29][cH:28]3)[n:27][c:26]2[cH:25]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15][c:16]([CH3:17])[n:18]... | COc1ccc2c(Nc3cc(C)n[nH]3)nc(Sc3ccc(NC(C)=O)cc3)nc2c1 | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccc(O)cc3n2)cc1 | null | null | ClCCl.ClC(C)Cl.C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(Sc2nc(Nc3ccn[nH]3)c3ccccc3n2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | null | [] | 80 | CELSIUS | 15 | HOUR | A solution of [2-(4-acetamidophenylsulfanyl)-7-methoxy-quinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (23 mg, 5.54.10−5 mol) in dichloroethane (3 mL) is treated with 1M BBr3 in dichloromethane (222 μL, 2.21.10−4 mol). The mixture os heated at 80° C. for 4 hours before 1M BBr3 in DCM (222 μL, 2.21.10−4 mol) is added.... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1cn[nH]c1.c1ccc2ncncc2c1 | Other | ClCCl.ClC(C)Cl.C(Cl)Cl | 80 | 15 | COc1ccc2c(Nc3cc(C)n[nH]3)nc(Sc3ccc(NC(C)=O)cc3)nc2c1>ClCCl.ClC(C)Cl.C(Cl)Cl>CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccc(O)cc3n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-413ab4abf64f40b2ac16799857468fde | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccc([N+](=O)[O-])cc3n2)cc1>>CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccc(NO)cc3n2)cc1 | C(C)(=O)NC1=CC=C(C=C1)SC1=NC2=CC(=CC=C2C(=N1)NC=1NN=C(C1)C)[N+](=O)[O-].[H][H]>>C(C)(=O)NC1=CC=C(C=C1)SC1=NC2=CC(=CC=C2C(=N1)NC=1NN=C(C1)C)NO | O=[N+:24]([c:23]1[cH:22][cH:21][c:20]2[c:12]([NH:13][c:14]3[cH:15][c:16]([CH3:17])[n:18][nH:19]3)[n:11][c:10]([S:9][c:8]3[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:30][cH:29]3)[n:28][c:27]2[cH:26]1)[O-:25]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15][c:16]([CH3... | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccc([N+](=O)[O-])cc3n2)cc1 | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccc(NO)cc3n2)cc1 | null | [Pd] | CO | Functional Group Interconversion | OtherReaction | 035e8e334c54db6485089fc974624221383ce2079ffd637bc0883c14dd7a36a6 | 30fd69eaae9316a77d843e872c35e0299532f4c1004874612b07f6d0d785f325 | c1ccc(Sc2nc(Nc3ccn[nH]3)c3ccccc3n2)cc1 | O=[N+;H0;D3:1](-[O-;H0;D1:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#7;a:7]>>[#7;a:7]:[c:6]:[c:5]:[c:3](-[NH;D2;+0:1]-[OH;D1;+0:2]):[c:4] | null | [] | null | null | null | null | To a solution of [2-(4-acetamido-phenylsulfanyl)-7-nitroquinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (147 mg, 3.38.10−4 mol) in methanol (5 mL) is added Pd/C 10% (40 mg) and the reaction mixture is treated with hydrogen at balloon pressure at 45° C. for 20 hours. The catalyst is filtered through a pad of celite wh... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Secondary amine | null | null | c1ccccc1.c1cn[nH]c1.c1ccc2ncncc2c1 | Other | [Pd].CO | null | null | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccc([N+](=O)[O-])cc3n2)cc1>[Pd].CO>CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccc(NO)cc3n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8eb6557b50af432584bae6d598ca99b8 | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccc([N+](=O)[O-])cc3n2)cc1>>CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccc(N)cc3n2)cc1 | C(C)(=O)NC1=CC=C(C=C1)SC1=NC2=CC(=CC=C2C(=N1)NC=1NN=C(C1)C)[N+](=O)[O-]>>C(C)(=O)NC1=CC=C(C=C1)SC1=NC2=CC(=CC=C2C(=N1)NC=1NN=C(C1)C)N | O=[N+:24]([O-])[c:23]1[cH:22][cH:21][c:20]2[c:12]([NH:13][c:14]3[cH:15][c:16]([CH3:17])[n:18][nH:19]3)[n:11][c:10]([S:9][c:8]3[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:29][cH:28]3)[n:27][c:26]2[cH:25]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15][c:16]([CH3:17... | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccc([N+](=O)[O-])cc3n2)cc1 | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccc(N)cc3n2)cc1 | null | [Fe] | CCO.O.CC(=O)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(Sc2nc(Nc3ccn[nH]3)c3ccccc3n2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[NH2;D1;+0:1]):[c:3] | null | [] | 90 | CELSIUS | 4 | HOUR | [2-(4-Acetamido-phenylsulfanyl)-7-nitroquinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (182 mg, 4.18.10−4 mol) is dissolved in a mixture EtOH/water/AcOH(25/10/1, 36 mL) and the reaction is heated at 90° C. Iron powder (93 mg) is added and the mixture is stirred at 90° C. for 4 hours, cooled to room temperature and fi... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1cn[nH]c1.c1ccc2ncncc2c1 | Other | [Fe].CCO.O.CC(=O)O | 90 | 4 | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccc([N+](=O)[O-])cc3n2)cc1>[Fe].CCO.O.CC(=O)O>CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)c3ccc(N)cc3n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-2c9f0fe041d94e3aa4d71ea144b51227 | CC(=O)Nc1ccc(S)cc1.Cc1cc(Nc2cc(-c3ccccc3)nc(Cl)n2)[nH]n1>>CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(-c3ccccc3)n2)cc1 | ClC1=NC(=CC(=N1)NC=1NN=C(C1)C)C1=CC=CC=C1.C(C)(=O)NC1=CC=C(C=C1)S>>C(C)(=O)NC1=CC=C(C=C1)SC1=NC(=CC(=N1)NC=1NN=C(C1)C)C1=CC=CC=C1 | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([SH:9])[cH:29][cH:30]1.Cl[c:10]1[n:11][c:12]([NH:13][c:14]2[cH:15][c:16]([CH3:17])[n:18][nH:19]2)[cH:20][c:21](-[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[n:28]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15][c:16]([C... | CC(=O)Nc1ccc(S)cc1.Cc1cc(Nc2cc(-c3ccccc3)nc(Cl)n2)[nH]n1 | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(-c3ccccc3)n2)cc1 | null | null | C(C)(C)(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution thiol | 58d609edf2d5c5dde8e0c437ccd45aa96794418033a2a125be3482e79a43194a | 97e4acce9b485bd597e518526ab4e9623782b1c9043b6e30dd257d386e3e5b01 | c1ccc(Sc2nc(Nc3ccn[nH]3)cc(-c3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[SH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[S;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | 85 | [{"value": 85.0, "product": "C(C)(=O)NC1=CC=C(C=C1)SC1=NC(=CC(=N1)NC=1NN=C(C1)C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The above prepared (2-chloro-6-phenyl-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine. (60 mg, 0.21 mmol) is combined with 4-acetamidothiophenol (176 mg, 1.05 mmol) in tert-butanol (5 mL) and the mixture heated at reflux for 20 hours. The reaction mixture is cooled to room temperature and partitioned between ethyl ace... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic thiol | Monosulfide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1cn[nH]c1.c1ccccc1 | HCl | C(C)(C)(C)O | null | null | CC(=O)Nc1ccc(S)cc1.Cc1cc(Nc2cc(-c3ccccc3)nc(Cl)n2)[nH]n1>C(C)(C)(C)O>CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(-c3ccccc3)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1178eba2922a40e785961547df669987 | COc1ccc(CSc2nc(Cl)cc(Cl)n2)cc1.Cc1cc(N)n[nH]1>>COc1ccc(CSc2nc(Cl)cc(Nc3cc(C)n[nH]3)n2)cc1 | [I-].[Na+].ClC1=NC(=NC(=C1)Cl)SCC1=CC=C(C=C1)OC.NC1=NNC(=C1)C.C(C)(C)N(CC)C(C)C>>ClC1=CC(=NC(=N1)SCC1=CC=C(C=C1)OC)NC=1NN=C(C1)C | Cl[c:14]1[cH:13][c:11]([Cl:12])[n:10][c:9]([S:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:24][cH:23]2)[n:22]1.[NH2:15][c:16]1[cH:17][c:18]([CH3:19])[nH:20][n:21]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][c:9]2[n:10][c:11]([Cl:12])[cH:13][c:14]([NH:15][c:16]3[cH:17][c:18]([CH3:19])[n:20][nH:21]3)[n:22]2)[... | COc1ccc(CSc2nc(Cl)cc(Cl)n2)cc1.Cc1cc(N)n[nH]1 | COc1ccc(CSc2nc(Cl)cc(Nc3cc(C)n[nH]3)n2)cc1 | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | OtherReaction | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CSc2nccc(Nc3ccn[nH]3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1.[C;D1;H3:9]-[c:10]1:[c:11]:[c:12](-[NH2;D1;+0:13]):[n;H0;D2;+0:14]:[nH;D2;+0:15]:1>>[#16:4]-[c:3]1:[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:[c;H0;D3;+0:1](-[NH;D2;+0:13]-[c:12]2:[c:11]:[c:10](-[C;D1;H3:9]):[n;H0;D2;+0:15]:[nH;D2;+0:14]:2):[#7;... | null | [] | 120 | CELSIUS | 15 | HOUR | To a solution of above-prepared 4,6-dichloro-2-(4-methoxy-benzylsulfanyl)-pyrimidine (915 mg, 3.04 mmol) and 3-amino-5-methylpyrazole (310 mg, 3.19 mmol) in BuOH (20 mL) is added diisopropylethylamine (0.56 mL, 3.19 mmol) followed by sodium iodide (455 mg, 3.04 mmol). The reaction mixture is stirred for 15 hours at 120... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1cn[nH]c1 | HCl | C(CCC)O | 120 | 15 | COc1ccc(CSc2nc(Cl)cc(Cl)n2)cc1.Cc1cc(N)n[nH]1>C(CCC)O>COc1ccc(CSc2nc(Cl)cc(Nc3cc(C)n[nH]3)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-757042ca9fea487cb62a9e76b97bc671 | CN1CCNCC1.COc1ccc(CSc2nc(Cl)cc(Nc3cc(C)n[nH]3)n2)cc1>>COc1ccc(CSc2nc(Nc3cc(C)n[nH]3)cc(N3CCN(C)CC3)n2)cc1 | ClC1=CC(=NC(=N1)SCC1=CC=C(C=C1)OC)NC=1NN=C(C1)C.CN1CCNCC1>>COC1=CC=C(CSC2=NC(=CC(=N2)NC=2NN=C(C2)C)N2CCN(CC2)C)C=C1 | [NH:21]1[CH2:22][CH2:23][N:24]([CH3:25])[CH2:26][CH2:27]1.Cl[c:20]1[cH:19][c:11]([NH:12][c:13]2[cH:14][c:15]([CH3:16])[n:17][nH:18]2)[n:10][c:9]([S:8][CH2:7][c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30][cH:29]2)[n:28]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][S:8][c:9]2[n:10][c:11]([NH:12][c:13]3[cH:14][c:15]([CH3:1... | CN1CCNCC1.COc1ccc(CSc2nc(Cl)cc(Nc3cc(C)n[nH]3)n2)cc1 | COc1ccc(CSc2nc(Nc3cc(C)n[nH]3)cc(N3CCN(C)CC3)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 89a9e7e1366d55004dcd9e6694ddaa661145a78e26c30f61d46c470b984e6100 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(CSc2nc(Nc3ccn[nH]3)cc(N3CCNCC3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6](-[#7:7]):[c:8]:1.[#7:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#16:4]-[c:3]1:[#7;a:5]:[c:6](-[#7:7]):[c:8]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:11]-[C:10]-[#7:9]-[C:14]-[C:13]-2):[#7;a:2]:1 | null | [] | null | null | null | null | The above-prepared [6-chloro-2-(4-methoxy-benzylsulfanyl)-pyrimidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine (500 mg, 1.38 mmol) in 1-methylpiperazine (10 mL) is heated at 130° C. for 15 hours. The solvent is then removed in vacuo and the residue is purified by flash chromatography (SiO2, dichloromethane/MeOH gradient) t... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1cncnc1 | c1cncnc1.C1C[NH]CC[NH]1 | c1ccccc1.c1cncnc1.c1cn[nH]c1.C1C[NH]CC[NH]1 | HCl | null | null | null | CN1CCNCC1.COc1ccc(CSc2nc(Cl)cc(Nc3cc(C)n[nH]3)n2)cc1>>COc1ccc(CSc2nc(Nc3cc(C)n[nH]3)cc(N3CCN(C)CC3)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8efc810cb17d4a09ab4b16028a84d79f | COc1ccc(-c2cc(Nc3cc(C)n[nH]3)nc(Sc3ccc(NC(C)=O)cc3)n2)cc1>>CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(-c3ccc(O)cc3)n2)cc1 | C(C)(=O)NC1=CC=C(C=C1)SC1=NC(=CC(=N1)NC=1NN=C(C1)C)C1=CC=C(C=C1)OC.B(Br)(Br)Br.B(Br)(Br)Br>>C(C)(=O)NC1=CC=C(C=C1)SC1=NC(=CC(=N1)NC=1NN=C(C1)C)C1=CC=C(C=C1)O | C[O:26][c:25]1[cH:24][cH:23][c:22](-[c:21]2[cH:20][c:12]([NH:13][c:14]3[cH:15][c:16]([CH3:17])[n:18][nH:19]3)[n:11][c:10]([S:9][c:8]3[cH:7][cH:6][c:5]([NH:4][C:2]([CH3:1])=[O:3])[cH:31][cH:30]3)[n:29]2)[cH:28][cH:27]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15][c:16... | COc1ccc(-c2cc(Nc3cc(C)n[nH]3)nc(Sc3ccc(NC(C)=O)cc3)n2)cc1 | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(-c3ccc(O)cc3)n2)cc1 | null | null | ClC(C)Cl.C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(Sc2nc(Nc3ccn[nH]3)cc(-c3ccccc3)n2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 80 | CELSIUS | 15 | HOUR | A solution of [2-(4-acetamido-phenyl-sulfanyl)-6-(4-methoxyphenyl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (100 mg, 2.24.10−4 mol) in dichloroethane (5 mL) is treated with 1M BBr3 in DCM (896 μL, 8.96.10−4 mol). The mixture is then heated at 80° C. for 4 hours before 1M BBr3 in DCM (896 μL, 8.96.10−4 mol) is a... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1cncnc1.c1cn[nH]c1.c1ccccc1 | Other | ClC(C)Cl.C(Cl)Cl | 80 | 15 | COc1ccc(-c2cc(Nc3cc(C)n[nH]3)nc(Sc3ccc(NC(C)=O)cc3)n2)cc1>ClC(C)Cl.C(Cl)Cl>CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(-c3ccc(O)cc3)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0efdd5c1443a48999efd22ef3044b4f4 | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(-c3ccc(O)cc3)n2)cc1.CN(C)CCCCl>>CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(-c3ccc(OCCCN(C)C)cc3)n2)cc1 | Cl.CN(CCCCl)C.C(C)(=O)NC1=CC=C(C=C1)SC1=NC(=CC(=N1)NC=1NN=C(C1)C)C1=CC=C(C=C1)O.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)NC1=CC=C(C=C1)SC1=NC(=CC(=N1)NC=1NN=C(C1)C)C1=CC=C(C=C1)OCCCN(C)C | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15][c:16]([CH3:17])[n:18][nH:19]3)[cH:20][c:21](-[c:22]3[cH:23][cH:24][c:25]([OH:26])[cH:33][cH:34]3)[n:35]2)[cH:36][cH:37]1.Cl[CH2:27][CH2:28][CH2:29][N:30]([CH3:31])[CH3:32]>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8](... | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(-c3ccc(O)cc3)n2)cc1.CN(C)CCCCl | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(-c3ccc(OCCCN(C)C)cc3)n2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(Sc2nc(Nc3ccn[nH]3)cc(-c3ccccc3)n2)cc1 | Cl-[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 | [] | 80 | CELSIUS | 4 | HOUR | To a solution of the above-prepared [2-(4-acetamido-phenyl-sulfanyl)-6-(4-hydroxyphenyl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (70 mg, 1.62.10−4 mol) in DMF (3 mL) is added potassium carbonate (134 mg, 9.71.10−4 mol). The reaction mixture is heated to 80° C. before 1-dimethylamino-3-chloropropane hydrochlori... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1cncnc1.c1cn[nH]c1.c1ccccc1 | HCl | CN(C)C=O | 80 | 4 | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(-c3ccc(O)cc3)n2)cc1.CN(C)CCCCl>CN(C)C=O>CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(-c3ccc(OCCCN(C)C)cc3)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7ca708bf4bfc4bdf89b496425cc3395e | CCC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(C(=O)OC)n2)cc1>>CCC(=O)Nc1ccc(Sc2nc(CO)cc(Nc3cc(C)n[nH]3)n2)cc1 | COC(=O)C1=CC(=NC(=N1)SC1=CC=C(C=C1)NC(CC)=O)NC=1NN=C(C1)C.[BH4-].[Li+]>>OCC1=CC(=NC(=N1)SC1=CC=C(C=C1)NC(CC)=O)NC=1NN=C(C1)C | C[O:15][C:14](=O)[c:13]1[n:12][c:11]([S:10][c:9]2[cH:8][cH:7][c:6]([NH:5][C:3]([CH2:2][CH3:1])=[O:4])[cH:27][cH:26]2)[n:25][c:17]([NH:18][c:19]2[cH:20][c:21]([CH3:22])[n:23][nH:24]2)[cH:16]1>>[CH3:1][CH2:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([S:10][c:11]2[n:12][c:13]([CH2:14][OH:15])[cH:16][c:17]([NH:18][c:19]3[... | CCC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(C(=O)OC)n2)cc1 | CCC(=O)Nc1ccc(Sc2nc(CO)cc(Nc3cc(C)n[nH]3)n2)cc1 | null | null | C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(Sc2nccc(Nc3ccn[nH]3)n2)cc1 | C-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1>>[OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:[c:8]:1 | null | [] | 50 | CELSIUS | 1.5 | HOUR | To a solution of [6-methoxycarbonyl-2-(4-propionylamino-phenyl-sulfanyl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (2 g, 4.85 mmol) in THF (100 mL) is added lithium borohydride (0.32 g, 14.5 mmol). The reaction mixture is stirred at 50° C. for 1.5 hours. The reaction is then quenched with dilute HCl and extracte... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1cncnc1.c1cn[nH]c1 | Other | C1CCOC1 | 50 | 1.5 | CCC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(C(=O)OC)n2)cc1>C1CCOC1>CCC(=O)Nc1ccc(Sc2nc(CO)cc(Nc3cc(C)n[nH]3)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b44cde9046554d3889ff52ec6590b1f4 | CSc1nc(Cl)cc(Cl)n1.Cc1cc(N)n[nH]1>>CSc1nc(Cl)cc(Nc2cc(C)n[nH]2)n1 | [I-].[Na+].ClC1=NC(=NC(=C1)Cl)SC.NC1=NNC(=C1)C.C(C)(C)N(CC)C(C)C>>ClC1=CC(=NC(=N1)SC)NC=1NN=C(C1)C | Cl[c:8]1[cH:7][c:5]([Cl:6])[n:4][c:3]([S:2][CH3:1])[n:16]1.[NH2:9][c:10]1[cH:11][c:12]([CH3:13])[nH:14][n:15]1>>[CH3:1][S:2][c:3]1[n:4][c:5]([Cl:6])[cH:7][c:8]([NH:9][c:10]2[cH:11][c:12]([CH3:13])[n:14][nH:15]2)[n:16]1 | CSc1nc(Cl)cc(Cl)n1.Cc1cc(N)n[nH]1 | CSc1nc(Cl)cc(Nc2cc(C)n[nH]2)n1 | null | null | C(CCC)O | Heteroatom Alkylation and Arylation | OtherReaction | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2ccn[nH]2)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1.[C;D1;H3:9]-[c:10]1:[c:11]:[c:12](-[NH2;D1;+0:13]):[n;H0;D2;+0:14]:[nH;D2;+0:15]:1>>[#16:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:13]-[c:12]2:[c:11]:[c:10](-[C;D1;H3:9]):[n;H0;D2;+0:15]:[nH;D2;+0:14]:2):[c:8]:[c:6](-[Cl;D1;H0:7]):[#7;... | null | [] | 120 | CELSIUS | 15 | HOUR | To a solution of 4,6-dichloro-2-methylsulfanyl-pyrimidine (5 g, 25.6 mmol) and 3-amino-5-methylpyrazole 2.61 g, 26.9 mmol) in BuOH (60 mL) is added diisopropylethylamine (4.69 mL, 26.9 mmol) followed by sodium iodide (3.84 g, 25.6 mmol). The reaction mixture is stirred for 15 hours at 120° C. The solvent is then remove... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1cn[nH]c1 | HCl | C(CCC)O | 120 | 15 | CSc1nc(Cl)cc(Cl)n1.Cc1cc(N)n[nH]1>C(CCC)O>CSc1nc(Cl)cc(Nc2cc(C)n[nH]2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4c797efee47e4a8493078424ee810033 | C1COCCN1.CSc1nc(Cl)cc(Nc2cc(C)n[nH]2)n1>>CSc1nc(Nc2cc(C)n[nH]2)cc(N2CCOCC2)n1 | ClC1=CC(=NC(=N1)SC)NC=1NN=C(C1)C.N1CCOCC1>>CSC1=NC(=CC(=N1)NC=1NN=C(C1)C)N1CCOCC1 | [NH:15]1[CH2:16][CH2:17][O:18][CH2:19][CH2:20]1.Cl[c:14]1[cH:13][c:5]([NH:6][c:7]2[cH:8][c:9]([CH3:10])[n:11][nH:12]2)[n:4][c:3]([S:2][CH3:1])[n:21]1>>[CH3:1][S:2][c:3]1[n:4][c:5]([NH:6][c:7]2[cH:8][c:9]([CH3:10])[n:11][nH:12]2)[cH:13][c:14]([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[n:21]1 | C1COCCN1.CSc1nc(Cl)cc(Nc2cc(C)n[nH]2)n1 | CSc1nc(Nc2cc(C)n[nH]2)cc(N2CCOCC2)n1 | null | null | null | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | b6ba2533a469a91b7ece94b4a523fa9d9d9bc584236787b5a2be96cdf7a917fc | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(Nc2cc(N3CCOCC3)ncn2)[nH]n1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[#16:4]):[#7;a:5]:[c:6](-[#7:7]):[c:8]:1.[#8:9]1-[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]-1>>[#16:4]-[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:12]2-[C:11]-[C:10]-[#8:9]-[C:14]-[C:13]-2):[c:8]:[c:6](-[#7:7]):[#7;a:5]:1 | null | [] | null | null | null | null | The above-prepared [6-chloro-2-methylsulfanyl-primidin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine (2.42 g, 9.46 mmol) is heated in morpholine (10 mL) at 130° C. for 15 hours. The solvent is then removed in vacuo and the solid residue is triturated in EtOH and collected by filtration to give [2-methylsulfanyl-6-(morpholin-4... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1cncnc1 | c1cncnc1.C1COCC[NH]1 | c1cncnc1.c1cn[nH]c1.C1COCC[NH]1 | HCl | null | null | null | C1COCCN1.CSc1nc(Cl)cc(Nc2cc(C)n[nH]2)n1>>CSc1nc(Nc2cc(C)n[nH]2)cc(N2CCOCC2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bc09a3a13dce4855b85b4efddef0a94f | CSc1nc(Nc2cc(C)n[nH]2)cc(N2CCOCC2)n1>>Cc1cc(Nc2cc(N3CCOCC3)nc(S(C)(=O)=O)n2)[nH]n1 | CSC1=NC(=CC(=N1)NC=1NN=C(C1)C)N1CCOCC1.CO.OOS(=O)[O-].[K+]>>CS(=O)(=O)C1=NC(=CC(=N1)NC=1NN=C(C1)C)N1CCOCC1 | [CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[cH:7][c:8]([N:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)[n:15][c:16]([S:17][CH3:18])[n:21]2)[nH:22][n:23]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[cH:7][c:8]([N:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)[n:15][c:16]([S:17]([CH3:18])(=[O:19])=[O:20])[n:21]2)[nH:22][n:23]1 | CSc1nc(Nc2cc(C)n[nH]2)cc(N2CCOCC2)n1 | Cc1cc(Nc2cc(N3CCOCC3)nc(S(C)(=O)=O)n2)[nH]n1 | null | null | O | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1cc(Nc2cc(N3CCOCC3)ncn2)[nH]n1 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7]>>[C;D1;H3:1]-[S;H0;D4;+0:2](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:3](:[#7;a:4]:[c:5]):[#7;a:6]:[c:7] | null | [] | null | null | 15 | HOUR | To a suspension of the above-prepared [2-methylsulfanyl-6-(morpholin-4-yl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (500 mg, 1.63 mmol) in MeOH (10 mL) is added a solution of oxone (3.0 g) in water (10 mL). The reaction mixture is stirred at room temperature for 15 hours and most of the solvent is evaporated. T... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1cn[nH]c1.c1cncnc1.C1COCC[NH]1 | null | O | null | 15 | CSc1nc(Nc2cc(C)n[nH]2)cc(N2CCOCC2)n1>O>Cc1cc(Nc2cc(N3CCOCC3)nc(S(C)(=O)=O)n2)[nH]n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1367579f6fb74257b840433719849b27 | CC(=O)Nc1ccc(S)cc1.Cc1cc(Nc2cc(N3CCOCC3)nc(S(C)(=O)=O)n2)[nH]n1>>CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(N3CCOCC3)n2)cc1 | CS(=O)(=O)C1=NC(=CC(=N1)NC=1NN=C(C1)C)N1CCOCC1.C(C)(=O)NC1=CC=C(C=C1)S>>C(C)(=O)NC1=CC=C(C=C1)SC1=NC(=CC(=N1)NC=1NN=C(C1)C)N1CCOCC1 | [CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([SH:9])[cH:29][cH:30]1.CS(=O)(=O)[c:10]1[n:11][c:12]([NH:13][c:14]2[cH:15][c:16]([CH3:17])[n:18][nH:19]2)[cH:20][c:21]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[n:28]1>>[CH3:1][C:2](=[O:3])[NH:4][c:5]1[cH:6][cH:7][c:8]([S:9][c:10]2[n:11][c:12]([NH:13][c:14]3[cH:15... | CC(=O)Nc1ccc(S)cc1.Cc1cc(Nc2cc(N3CCOCC3)nc(S(C)(=O)=O)n2)[nH]n1 | CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(N3CCOCC3)n2)cc1 | null | null | C(C)(C)(C)O | Heteroatom Alkylation and Arylation | OtherReaction | ddd1ac26706dc5e92522f5d3d269105f75799b9c4e7e14a0ab93373adafa0dd6 | f2e0bb31edbeb92a7317d787d4b892418ccdf9fe3a4c00c7fbe8e3075b7e8833 | c1ccc(Sc2nc(Nc3ccn[nH]3)cc(N3CCOCC3)n2)cc1 | C-S(=O)(=O)-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[SH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[S;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | The above-prepared [2-methylsulfonyl-6-(morpholin-4-yl)-pyrimidin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (178 mg, 0.52 mmol) and 4-acetamidothiophenol (176 mg, 1.05 mmol) are refluxed in tert-butanol (5 mL) over 20 h. The reaction mixture is cooled to room temperature and partitioned between ethyl acetate and aqueous N... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic thiol.Sulfone | Monosulfide | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1cn[nH]c1.C1COCC[NH]1 | HO- | C(C)(C)(C)O | null | null | CC(=O)Nc1ccc(S)cc1.Cc1cc(Nc2cc(N3CCOCC3)nc(S(C)(=O)=O)n2)[nH]n1>C(C)(C)(C)O>CC(=O)Nc1ccc(Sc2nc(Nc3cc(C)n[nH]3)cc(N3CCOCC3)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5fd004ade2724ee281d151c8731afb6f | Cc1cc(Nc2nc(Nc3ccc(NC(=O)OC(C)(C)C)cc3)nc3ccccc23)[nH]n1>>Cc1cc(Nc2nc(Nc3ccc(N)cc3)nc3ccccc23)[nH]n1 | C(C)(C)(C)OC(=O)NC1=CC=C(C=C1)NC1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C>>NC1=CC=C(C=C1)NC1=NC2=CC=CC=C2C(=N1)NC=1NN=C(C1)C | CC(C)(C)OC(=O)[NH:14][c:13]1[cH:12][cH:11][c:10]([NH:9][c:8]2[n:7][c:6]([NH:5][c:4]3[cH:3][c:2]([CH3:1])[n:25][nH:24]3)[c:23]3[c:18]([n:17]2)[cH:19][cH:20][cH:21][cH:22]3)[cH:16][cH:15]1>>[CH3:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[n:7][c:8]([NH:9][c:10]3[cH:11][cH:12][c:13]([NH2:14])[cH:15][cH:16]3)[n:17][c:18]3[cH:19][cH:2... | Cc1cc(Nc2nc(Nc3ccc(NC(=O)OC(C)(C)C)cc3)nc3ccccc23)[nH]n1 | Cc1cc(Nc2nc(Nc3ccc(N)cc3)nc3ccccc23)[nH]n1 | null | null | C(Cl)Cl.C(=O)(C(F)(F)F)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(Nc2nc(Nc3ccn[nH]3)c3ccccc3n2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 2 | HOUR | A solution of [2-(4-tert-Butoxycarbonylamino-phenylamino)-quinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (IIc-60, 100 mg, 0.232 mmol) in a mixture of DCM/TFA (5/1, 12 mL) was stirred for 2 hours at room temperature. The solvents were removed in vacuo and the residue triturated in aqueous K2CO3. The resulting solid w... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1cn[nH]c1.c1ccccc1.c1ccc2ncncc2c1 | HO- | C(Cl)Cl.C(=O)(C(F)(F)F)O | null | 2 | Cc1cc(Nc2nc(Nc3ccc(NC(=O)OC(C)(C)C)cc3)nc3ccccc23)[nH]n1>C(Cl)Cl.C(=O)(C(F)(F)F)O>Cc1cc(Nc2nc(Nc3ccc(N)cc3)nc3ccccc23)[nH]n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-35c861d6b82946f599930c0c25b7c1b1 | Clc1cc(Cl)nc(Cl)n1.Nc1cc(C2CC2)[nH]n1>>Clc1cc(Nc2cc(C3CC3)n[nH]2)nc(Cl)n1 | ClC1=NC(=CC(=N1)Cl)Cl.NC1=NNC(=C1)C1CC1.C(C)N(CC)CC>>C1(CC1)C=1C=C(NN1)NC1=NC(=NC(=C1)Cl)Cl | Cl[c:4]1[cH:3][c:2]([Cl:1])[n:17][c:15]([Cl:16])[n:14]1.[NH2:5][c:6]1[cH:7][c:8]([CH:9]2[CH2:10][CH2:11]2)[nH:12][n:13]1>>[Cl:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[n:12][nH:13]2)[n:14][c:15]([Cl:16])[n:17]1 | Clc1cc(Cl)nc(Cl)n1.Nc1cc(C2CC2)[nH]n1 | Clc1cc(Nc2cc(C3CC3)n[nH]2)nc(Cl)n1 | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(Nc2cc(C3CC3)n[nH]2)ncn1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:1.[C:9]-[c:10]1:[c:11]:[c:12](-[NH2;D1;+0:13]):[n;H0;D2;+0:14]:[nH;D2;+0:15]:1>>[C:9]-[c:10]1:[c:11]:[c:12](-[NH;D2;+0:13]-[c;H0;D3;+0:1]2:[#7;a:2]:[c:3](-[Cl;D1;H0:4]):[#7;a:5]:[c:6](-[Cl;D1;H0:7]):[c:8]:2):[nH;D2;+0:14]:[n;H0;D2;+0:1... | 80 | [{"value": 80.0, "product": "C1(CC1)C=1C=C(NN1)NC1=NC(=NC(=C1)Cl)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.8, "product": "C1(CC1)C=1C=C(NN1)NC1=NC(=NC(=C1)Cl)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | To a solution of-2,4,6-trichloropyrimidine (600 mg, 3.27 mmol) and 3-amino-5-cyclopropylpyrazole (403 mg, 3.27 mmol) in EtOH (10 mL) was added triethylamine (456 μL, 3.27 mmol) and the reaction mixture was stirred for 15 hours at room temperature. The solvent was evaporated and the residue was purified by flash chromat... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1cn[nH]c1.C1CC1 | HCl | CCO | null | 15 | Clc1cc(Cl)nc(Cl)n1.Nc1cc(C2CC2)[nH]n1>CCO>Clc1cc(Nc2cc(C3CC3)n[nH]2)nc(Cl)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-728c17a2fdab40acbb68bf4459bb997a | Clc1cc(Nc2cc(C3CC3)n[nH]2)nc(Cl)n1.Sc1ccc2ccccc2c1>>Clc1cc(Nc2cc(C3CC3)n[nH]2)nc(Sc2ccc3ccccc3c2)n1 | C1(CC1)C=1C=C(NN1)NC1=NC(=NC(=C1)Cl)Cl.C1=C(C=CC2=CC=CC=C12)S.C(C)N(CC)CC>>ClC1=CC(=NC(=N1)SC1=CC2=CC=CC=C2C=C1)NC=1NN=C(C1)C1CC1 | Cl[c:15]1[n:14][c:4]([NH:5][c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[n:12][nH:13]2)[cH:3][c:2]([Cl:1])[n:27]1.[SH:16][c:17]1[cH:18][cH:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[cH:26]1>>[Cl:1][c:2]1[cH:3][c:4]([NH:5][c:6]2[cH:7][c:8]([CH:9]3[CH2:10][CH2:11]3)[n:12][nH:13]2)[n:14][c:15]([S:16][c:17]2[cH:18][cH:19]... | Clc1cc(Nc2cc(C3CC3)n[nH]2)nc(Cl)n1.Sc1ccc2ccccc2c1 | Clc1cc(Nc2cc(C3CC3)n[nH]2)nc(Sc2ccc3ccccc3c2)n1 | null | null | C(C)(C)(C)O | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution thiol | 58d609edf2d5c5dde8e0c437ccd45aa96794418033a2a125be3482e79a43194a | 97e4acce9b485bd597e518526ab4e9623782b1c9043b6e30dd257d386e3e5b01 | c1ccc2cc(Sc3nccc(Nc4cc(C5CC5)n[nH]4)n3)ccc2c1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[SH;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:8]:[c:7](-[S;H0;D2;+0:6]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5]):[c:9] | null | [] | null | null | null | null | To a solution of (5-cyclopropyl-2H-pyrazol-3-yl)-(2,6-dichloropyrimidin-4-yl)-amine (211 mg, 0.781 mmol) and 2-naphthalenethiol (125 mg, 0.781 mmol) in tert-butanol (5 mL) was added triethylamine (174 μL, 1.25 mmol) and the resulting mixture was heated at reflux for 15 hours. The reaction mixture was cooled to room tem... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic thiol | Monosulfide | c1cncnc1 | c1cncnc1 | c1cncnc1.c1cn[nH]c1.C1CC1.c1ccc2ccccc2c1 | HCl | C(C)(C)(C)O | null | null | Clc1cc(Nc2cc(C3CC3)n[nH]2)nc(Cl)n1.Sc1ccc2ccccc2c1>C(C)(C)(C)O>Clc1cc(Nc2cc(C3CC3)n[nH]2)nc(Sc2ccc3ccccc3c2)n1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7db9ee3861144166bfa97d305c987b83 | CC(=O)O.N=CN.Nc1cc(F)ccc1C(=O)O.O=c1[nH]cnc2cc(F)ccc12>>NC(=O)Cn1cnc2cc(OCc3cccc(F)c3)ccc2c1=O | FC1=CC=C2C(NC=NC2=C1)=O.NC1=C(C(=O)O)C=CC(=C1)F.C(C)(=O)O.C(=N)N.COCCO>>FC=1C=C(COC2=CC=C3C(N(C=NC3=C2)CC(=O)N)=O)C=CC1 | O=C(O)[CH3:4].N[CH:2]=[NH:1].N[c:13]1[c:14]([C:12](=[O:3])[OH:11])[cH:15][cH:16][c:17]([F:18])[cH:19]1.F[c:10]1[cH:9][c:8]2[n:7][cH:6][nH:5][c:23](=[O:24])[c:22]2[cH:21][cH:20]1>>[NH2:1][C:2](=[O:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[cH:9][c:10]([O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][c:17]([F:18])[cH:19]3)[cH:20][cH:21... | CC(=O)O.N=CN.Nc1cc(F)ccc1C(=O)O.O=c1[nH]cnc2cc(F)ccc12 | NC(=O)Cn1cnc2cc(OCc3cccc(F)c3)ccc2c1=O | null | null | N | C-C Coupling | OtherReaction | 549469b0202a82f6d49115e1691bca38d499b69425cdeb0b97f6487c8974c66c | 4531a90f0e38b1292d59c72a3d7046afc75031f3dc888520e34f4404c682d343 | O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | F-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]2:[c:5](=[O;D1;H0:6]):[nH;D2;+0:7]:[c:8]:[#7;a:9]:[c:10]:2:[c:11]:1.N-[CH;D2;+0:12]=[NH;D1;+0:13].N-[c;H0;D3;+0:14]1:[c:15]:[c:16]:[c:17]:[c:18]:[c;H0;D3;+0:19]:1-[C;H0;D3;+0:20](=[O;H0;D1;+0:21])-[OH;D1;+0:22].O-C(=O)-[CH3;D1;+0:23]>>[NH2;D1;+0:13]-[C;H0;D3;+0:12](=[O;H0;D1;+0:21])-[... | 81 | [{"value": 81.0, "product": "FC=1C=C(COC2=CC=C3C(N(C=NC3=C2)CC(=O)N)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | null | null | 7-Fluoro-3H-quinazolin-4-one: A mixture of 2-amino-4-fluorobenzoic acid (14.6 g, 94 mmol) and formamidine acetate (19.6 g, 18.8 mmol) in 2-methoxyethanol (110 mL) was heated at 130° C. for 18 h. After cooling, the mixture was half evaporated and an off-white solid formed. The mixture was diluted with ammonia (25%, 10 m... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Carboxylic acid.Primary amine.Primary amine | Ether.Primary amide | c1ccccc1.c1ccc2cncnc2c1 | c1ccc2ncncc2c1.c1ccccc1 | c1ccc2ncncc2c1.c1ccccc1 | HF | N | 130 | null | CC(=O)O.N=CN.Nc1cc(F)ccc1C(=O)O.O=c1[nH]cnc2cc(F)ccc12>N>NC(=O)Cn1cnc2cc(OCc3cccc(F)c3)ccc2c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-af083bdcb1c9493f8949656570ce9951 | O=c1[nH]cnc2cc(F)ccc12.O=c1[nH]cnc2cc(OCc3cccc(F)c3)ccc12.OCc1cccc(F)c1>>NC(=O)Cn1cnc2cc(OCc3cccc(F)c3)ccc2c1=O | FC1=CC=C2C(NC=NC2=C1)=O.FC=1C=C(COC2=CC=C3C(NC=NC3=C2)=O)C=CC1.[Na].FC=1C=C(CO)C=CC1.Cl>>FC=1C=C(COC2=CC=C3C(N(C=NC3=C2)CC(=O)N)=O)C=CC1 | Fc1ccc2c(c1)n[cH:4][nH:1][c:2]2=[O:3].Fc1cccc(CO[c:10]2[cH:9][c:8]3[n:7][cH:6][nH:5][c:23](=[O:24])[c:22]3[cH:21][cH:20]2)c1.[OH:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]([F:18])[cH:19]1>>[NH2:1][C:2](=[O:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[cH:9][c:10]([O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][c:17]([F:18])[cH:19]3)... | O=c1[nH]cnc2cc(F)ccc12.O=c1[nH]cnc2cc(OCc3cccc(F)c3)ccc12.OCc1cccc(F)c1 | NC(=O)Cn1cnc2cc(OCc3cccc(F)c3)ccc2c1=O | null | null | O | C-C Coupling | OtherReaction | bed91af7e0dfd86a2bae7c4419293a420d3f8d784a049c87024c9c900614700a | 7c4d302c8467be036fd940fc99c2e6697f2f6f6416e3c475fd55db0fa07f890d | O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | F-c1:c:c:c2:[c;H0;D3;+0:1](=[O;D1;H0:2]):[nH;D2;+0:3]:[cH;D2;+0:4]:n:c:2:c:1.F-c1:c:c:c:c(-C-O-[c;H0;D3;+0:5]2:[c:6]:[c:7]:[c:8]3:[c:9](=[O;D1;H0:10]):[nH;D2;+0:11]:[c:12]:[#7;a:13]:[c:14]:3:[c:15]:2):c:1.[OH;D1;+0:16]-[C:17]-[c:18]>>[NH2;D1;+0:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:4]-[n;H0;D3;+0:11]1:[c:12]:[#7;a... | 61 | [{"value": 61.0, "product": "FC=1C=C(COC2=CC=C3C(N(C=NC3=C2)CC(=O)N)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 7-(3-Fluoro-benzyloxy)-3H-quinazolin-4-one: Sodium (1.8 g, 78.6 mmol) was added portionwise to 3-fluorobenzyl alcohol and the resulting mixture heated at 80–90° C. for 4 h under Argon. The resulting suspension was cooled to rt and 7-fluoro-3H-quinazolin-4-one (3.2 g, 19.5 mmol) was added and the resulting mixture heate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Primary alcohol | Ether.Primary amide | c1ncnc2ccccc12.c1ccccc1.c1ccc2cncnc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | HF | O | null | null | O=c1[nH]cnc2cc(F)ccc12.O=c1[nH]cnc2cc(OCc3cccc(F)c3)ccc12.OCc1cccc(F)c1>O>NC(=O)Cn1cnc2cc(OCc3cccc(F)c3)ccc2c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-02ebb08f2555436889139e7598c8df89 | O=c1[nH]cnc2cc(F)ccc12.O=c1[nH]cnc2cc(OCc3ccc(F)cc3)ccc12.OCc1ccc(F)cc1>>NC(=O)Cn1cnc2cc(OCc3ccc(F)cc3)ccc2c1=O | FC1=CC=C(COC2=CC=C3C(NC=NC3=C2)=O)C=C1.[H-].[Na+].FC1=CC=C(CO)C=C1.FC1=CC=C2C(NC=NC2=C1)=O.Cl>>FC1=CC=C(COC2=CC=C3C(N(C=NC3=C2)CC(=O)N)=O)C=C1 | Fc1ccc2c(=[O:3])[nH:1]cnc2c1.Fc1cc[c:2]([CH2:4]O[c:10]2[cH:9][c:8]3[n:7][cH:6][nH:5][c:23](=[O:24])[c:22]3[cH:21][cH:20]2)cc1.[OH:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]1>>[NH2:1][C:2](=[O:3])[CH2:4][n:5]1[cH:6][n:7][c:8]2[cH:9][c:10]([O:11][CH2:12][c:13]3[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]3... | O=c1[nH]cnc2cc(F)ccc12.O=c1[nH]cnc2cc(OCc3ccc(F)cc3)ccc12.OCc1ccc(F)cc1 | NC(=O)Cn1cnc2cc(OCc3ccc(F)cc3)ccc2c1=O | null | null | CN(C)C=O | Acylation | OtherReaction | 03403230c21435aad0b4dc99b0797e609f6e9d2d08f3b26bb8fbaf89983c1c02 | 4f1aeb4e78f799ea8fec67f5bb3932558106a9750f34e478520e711e3a816e1b | O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | F-c1:c:c:[c;H0;D3;+0:1](-[CH2;D2;+0:2]-O-[c;H0;D3;+0:3]2:[c:4]:[c:5]:[c:6]3:[c:7](=[O;D1;H0:8]):[nH;D2;+0:9]:[c:10]:[#7;a:11]:[c:12]:3:[c:13]:2):c:c:1.F-c1:c:c:c2:c(=[O;H0;D1;+0:14]):[nH;D2;+0:15]:c:n:c:2:c:1.[OH;D1;+0:16]-[C:17]-[c:18]>>[NH2;D1;+0:15]-[C;H0;D3;+0:1](=[O;H0;D1;+0:14])-[CH2;D2;+0:2]-[n;H0;D3;+0:9]1:[c:1... | 66 | [{"value": 66.0, "product": "FC1=CC=C(COC2=CC=C3C(N(C=NC3=C2)CC(=O)N)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | 7-(4-Fluoro-benzyloxy)-3H-quinazolin-4-one: A mixture of sodium hydride (55%, 3.2 g, 73 mmol), 4-fluorobenzyl alcohol (9.2 g, 73 mmol) and 7-fluoro-3H-quinazolin-4-one (3.0 g, 18 mmol) in DMF (75 mL) was heated at 140° C. for 2 h. The resulting suspension was cooled to rt and the mixture acidified to pH 3 with HCl (con... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ether.Primary alcohol | Ether.Primary amide | c1ccc2ncncc2c1.c1ccccc1.c1ccc2cncnc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | HF | CN(C)C=O | 140 | null | O=c1[nH]cnc2cc(F)ccc12.O=c1[nH]cnc2cc(OCc3ccc(F)cc3)ccc12.OCc1ccc(F)cc1>CN(C)C=O>NC(=O)Cn1cnc2cc(OCc3ccc(F)cc3)ccc2c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f243056d574b4911b9c3d4786237c32f | COC(=O)c1ccc(F)cc1[N+](=O)[O-].COC(=O)c1ccc(OCc2cccc(F)c2)cc1[N+](=O)[O-].O=C(OCc1cccc(F)c1)c1ccc(OCc2cccc(F)c2)cc1[N+](=O)[O-].OCc1cccc(F)c1>>Cc1nc2cc(OCc3cccc(F)c3)ccc2c(=O)n1CC(N)=O | FC=1C=C(COC(C2=C(C=C(C=C2)OCC2=CC(=CC=C2)F)[N+](=O)[O-])=O)C=CC1.COC(C1=C(C=C(C=C1)OCC1=CC(=CC=C1)F)[N+](=O)[O-])=O.COC(C1=C(C=C(C=C1)F)[N+](=O)[O-])=O.FC=1C=C(CO)C=CC1.C([O-])([O-])=O.[K+].[K+]>>FC=1C=C(COC2=CC=C3C(N(C(=NC3=C2)C)CC(=O)N)=O)C=CC1 | O=C(O[CH3:1])c1cc[c:2](F)c[c:22]1[N+:21](=O)[O-].CO[C:19]([c:18]1[c:4]([N+:3](=O)[O-])[cH:5][c:6](OCc2cccc(F)c2)[cH:16][cH:17]1)=[O:20].O=C(OCc1cccc(F)c1)c1ccc(OCc2cccc(F)c2)cc1[N+:24](=O)[O-].[OH:7][CH2:8][c:9]1[cH:10][cH:11][cH:12][c:13]([F:14])[cH:15]1>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([O:7][CH2:8][c:9]3[cH:10][c... | COC(=O)c1ccc(F)cc1[N+](=O)[O-].COC(=O)c1ccc(OCc2cccc(F)c2)cc1[N+](=O)[O-].O=C(OCc1cccc(F)c1)c1ccc(OCc2cccc(F)c2)cc1[N+](=O)[O-].OCc1cccc(F)c1 | Cc1nc2cc(OCc3cccc(F)c3)ccc2c(=O)n1CC(N)=O | null | null | O.CN(C)C=O | Acylation | OtherReaction | 0dcc5c66d238bdc66d7c9ad2d52e72f6fa8adb7e75a7ff817d86f27e067ec6f8 | 490600846d1bec08de2cf41b30e59049bb5d234d7c7d5a56860405909d038af6 | O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6](-O-C-c2:c:c:c:c(-F):c:2):[c:7]:[c:8]:1-[N+;H0;D3:9](=O)-[O-].F-[c;H0;D3;+0:10]1:c:c:c(-C(=O)-O-[CH3;D1;+0:11]):[c;H0;D3;+0:12](-[N+;H0;D3:13](=O)-[O-]):c:1.F-c1:c:c:c:c(-C-O-C(=O)-c2:c:c:c(-O-C-c3:c:c:c:c(-F):c:3):c:c:2-[N+;H0;D3:14](=O)-[O-]):c:1.[OH;D... | 76 | [{"value": 76.0, "product": "FC=1C=C(COC2=CC=C3C(N(C(=NC3=C2)C)CC(=O)N)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | 4-(3-Fluoro-benzyloxy)-2-nitro-benzoic acid (3-fluoro-benzyl) ester and 4-(3-fluoro-benzyloxy)-2-nitro-benzoic acid methyl ester: A mixture of 4-fluoro-2-nitro-benzoic acid methyl ester (9.2 g, 46.3 mmol), 3-fluorobenzyl alcohol (16.7 g, 132.4 mmol) and potassium carbonate (12.8 g, 92.6 mmol) in DMF (210 mL) was heated... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Aromatic halide.Ester.Ester.Ester.Ether.Ether.Nitro group.Nitro group.Nitro group.Primary alcohol | Ether.Primary amide | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | HF | O.CN(C)C=O | 65 | null | COC(=O)c1ccc(F)cc1[N+](=O)[O-].COC(=O)c1ccc(OCc2cccc(F)c2)cc1[N+](=O)[O-].O=C(OCc1cccc(F)c1)c1ccc(OCc2cccc(F)c2)cc1[N+](=O)[O-].OCc1cccc(F)c1>O.CN(C)C=O>Cc1nc2cc(OCc3cccc(F)c3)ccc2c(=O)n1CC(N)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ad3689421b0444ecba177dceb56a6917 | COC(=O)c1ccc(OCc2cccc(F)c2)cc1[N+](=O)[O-].O=C(O)c1ccc(OCc2cccc(F)c2)cc1[N+](=O)[O-].O=C(OCc1cccc(F)c1)c1ccc(OCc2cccc(F)c2)cc1[N+](=O)[O-]>>Cc1nc2cc(OCc3cccc(F)c3)ccc2c(=O)n1CC(N)=O | O.[OH-].[Li+].FC=1C=C(COC2=CC(=C(C(=O)O)C=C2)[N+](=O)[O-])C=CC1.FC=1C=C(COC(C2=C(C=C(C=C2)OCC2=CC(=CC=C2)F)[N+](=O)[O-])=O)C=CC1.COC(C1=C(C=C(C=C1)OCC1=CC(=CC=C1)F)[N+](=O)[O-])=O.C1CCOC1.[OH-].[Na+]>>FC=1C=C(COC2=CC=C3C(N(C(=NC3=C2)C)CC(=O)N)=O)C=CC1 | CO[C:2](c1ccc(OCc2cccc(F)c2)c[c:22]1[N+:21](=O)[O-])=[O:25].O=[C:23](O)c1ccc(OCc2cccc(F)c2)cc1[N+:24](=O)[O-].O=[N+:3]([O-])[c:4]1[cH:5][c:6]([O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][c:13]([F:14])[cH:15]2)[cH:16][cH:17][c:18]1[C:19](OCc1cccc(F)c1)=[O:20]>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([O:7][CH2:8][c:9]3[cH:10][cH:... | COC(=O)c1ccc(OCc2cccc(F)c2)cc1[N+](=O)[O-].O=C(O)c1ccc(OCc2cccc(F)c2)cc1[N+](=O)[O-].O=C(OCc1cccc(F)c1)c1ccc(OCc2cccc(F)c2)cc1[N+](=O)[O-] | Cc1nc2cc(OCc3cccc(F)c3)ccc2c(=O)n1CC(N)=O | null | null | O | Functional Group Interconversion | OtherReaction | 6b150b2195eaf16fb706d66fce584d6e08e3ff848185413dc1e98ebba7f3f78d | 2a0b1eba7259146293dd8a05c0847ad54599a0ec616dcea0e6fd6b7892fb527c | O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-c1:c:c:c(-O-C-c2:c:c:c:c(-F):c:2):c:[c;H0;D3;+0:3]:1-[N+;H0;D3:4](=O)-[O-].F-c1:c:c:c:c(-C-O-[C;H0;D3;+0:5](=[O;D1;H0:6])-[c:7](:[c:8]):[c:9](-[N+;H0;D3:10](=O)-[O-]):[c:11]):c:1.F-c1:c:c:c:c(-C-O-c2:c:c:c(-[C;H0;D3;+0:12](-O)=O):c(-[N+;H0;D3:13](=O)-[O-]):c:2):c:1>>[C;D1;H3:14]-[c;H... | 65 | [{"value": 65.0, "product": "FC=1C=C(COC2=CC=C3C(N(C(=NC3=C2)C)CC(=O)N)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | 4-(3-Fluoro-benzyloxy)-2-nitro-benzoic acid: A mixture of 4-(3-fluorobenzyloxy)-2-nitro-benzoic acid (3-fluoro-benzyl) ester and 4-(3-fluoro-benzyloxy)-2-nitro-benzoic acid methyl ester (14.0 g, 35.0 mmol) in THF (120 mL) and water (120 mL), containing lithium hydroxide monohydrate (2.94 g, 70.1 mmol) was stirred at rt... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic halide.Carboxylic acid.Ester.Ester.Ether.Ether.Nitro group.Nitro group.Nitro group | Primary amide | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | HF | O | null | 48 | COC(=O)c1ccc(OCc2cccc(F)c2)cc1[N+](=O)[O-].O=C(O)c1ccc(OCc2cccc(F)c2)cc1[N+](=O)[O-].O=C(OCc1cccc(F)c1)c1ccc(OCc2cccc(F)c2)cc1[N+](=O)[O-]>O>Cc1nc2cc(OCc3cccc(F)c3)ccc2c(=O)n1CC(N)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b61c6f8fbaaa4529848801b75a7c15ca | CCOC(=O)C(N)=O.Cc1nc2cc(OCc3cccc(F)c3)ccc2c(=O)[nH]1>>Cc1nc2cc(OCc3cccc(F)c3)ccc2c(=O)n1CC(N)=O | C[O-].[Na+].FC=1C=C(COC2=CC=C3C(NC(=NC3=C2)C)=O)C=CC1.NC1=C(C(=O)O)C=CC(=C1)OCC1=CC(=CC=C1)F.CCOC(=O)C(=O)N.Cl.CCOC(=O)C(=O)N.Cl.C[O-].[Na+]>>FC=1C=C(COC2=CC=C3C(N(C(=NC3=C2)C)CC(=O)N)=O)C=CC1 | CCO[C:22](=O)[C:23]([NH2:24])=[O:25].[CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][c:13]([F:14])[cH:15]3)[cH:16][cH:17][c:18]2[c:19](=[O:20])[nH:21]1>>[CH3:1][c:2]1[n:3][c:4]2[cH:5][c:6]([O:7][CH2:8][c:9]3[cH:10][cH:11][cH:12][c:13]([F:14])[cH:15]3)[cH:16][cH:17][c:18]2[c:19](=[O:20])[n:21... | CCOC(=O)C(N)=O.Cc1nc2cc(OCc3cccc(F)c3)ccc2c(=O)[nH]1 | Cc1nc2cc(OCc3cccc(F)c3)ccc2c(=O)n1CC(N)=O | null | null | CO.O | Heteroatom Alkylation and Arylation | OtherReaction | 1da9753d644c6fa0007c453f45cc4fc18aaa4054d5e85e90d8b695b83806fed4 | 233aaacfc76269f11fc4fe9f050f54668996773437c5330e6156d6b96147e87d | O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | C-C-O-[C;H0;D3;+0:1](=O)-[C:2](-[N;D1;H2:3])=[O;D1;H0:4].[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[c:10](=[O;D1;H0:11]):[nH;D2;+0:12]:1>>[C;D1;H3:5]-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[c:10](=[O;D1;H0:11]):[n;H0;D3;+0:12]:1-[CH2;D2;+0:1]-[C:2](-[N;D1;H2:3])=[O;D1;H0:4] | 97 | [{"value": 97.0, "product": "FC=1C=C(COC2=CC=C3C(N(C(=NC3=C2)C)CC(=O)N)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | 7-(3-Fluoro-benzyloxy)-2-methyl-3H-quinazolin-4-one: To a mixture of 2-amino-4-(3-fluoro-benzyloxy)-benzoic acid (2.0 g, 7.7 mmol) and ethyl acetamidate HCl (1.9 g, 15.3 mmol) in methanol (30 mL) was added sodium methoxide (5.4 M, 0.83 g, 15.3 mmol) and the resulting mixture was heated under reflux for 19 h. After this... | 10.6084/m9.figshare.5104873.v1 | null | Ester | null | c1ccc2cncnc2c1 | c1ccc2ncncc2c1 | c1ccc2ncncc2c1.c1ccccc1 | HO- | CO.O | null | 2 | CCOC(=O)C(N)=O.Cc1nc2cc(OCc3cccc(F)c3)ccc2c(=O)[nH]1>CO.O>Cc1nc2cc(OCc3cccc(F)c3)ccc2c(=O)n1CC(N)=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-29111edc181f4bb49fd521e1721d15d2 | CC(C)c1nc2cc(OCc3cccc(F)c3)ccc2c(=O)n1CC(N)=O>>CC(C)c1nc2cc(OCc3cccc(F)c3)ccc2c(=O)n1CC#N | FC=1C=C(COC2=CC=C3C(N(C(=NC3=C2)C(C)C)CC(=O)N)=O)C=CC1.C(O)([O-])=O.[Na+]>>FC=1C=C(COC2=CC=C3C(N(C(=NC3=C2)C(C)C)CC#N)=O)C=CC1 | O=[C:25]([CH2:24][n:23]1[c:4]([CH:2]([CH3:1])[CH3:3])[n:5][c:6]2[cH:7][c:8]([O:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][c:15]([F:16])[cH:17]3)[cH:18][cH:19][c:20]2[c:21]1=[O:22])[NH2:26]>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][c:6]2[cH:7][c:8]([O:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][c:15]([F:16])[cH:17]3)[cH:18][cH:19][c:20... | CC(C)c1nc2cc(OCc3cccc(F)c3)ccc2c(=O)n1CC(N)=O | CC(C)c1nc2cc(OCc3cccc(F)c3)ccc2c(=O)n1CC#N | null | null | ClCCl.CN(C=O)C | Miscellaneous | OtherReaction | 5094e9d814705bbdc421edbf7e9198e499e70e93916e2cec6eefbc82d1ba5440 | 32b9893bcb5223559a9d02852f8392cf6473aacfb044a52ba4e9cb9c29edb170 | O=c1[nH]cnc2cc(OCc3ccccc3)ccc12 | O=[C;H0;D3;+0:1](-[NH2;D1;+0:2])-[C:3]-[#7;a:4]>>[#7;a:4]-[C:3]-[C;H0;D2;+0:1]#[N;H0;D1;+0:2] | 55 | [{"value": 55.0, "product": "FC=1C=C(COC2=CC=C3C(N(C(=NC3=C2)C(C)C)CC#N)=O)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.9, "product": "FC=1C=C(COC2=CC=C3C(N(C(=NC3=C2)C(C)C)CC#N)=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | null | null | To a mixture of 2-[7-(3-fluoro-benzyloxy)-2-isopropyl-4-oxo-4H-quinazolin-3-yl]-acetamide (50 mg, 0.14 mmol) in dimethylformamide (0.5 mL), dichloromethane (2 mL) was added N-ethyl-N,N-diispropylamine (26.2 mg, 0.2 mmol) and the resulting mixture cooled to −78° C. Then trifluorosulfonic anhydride (49.6 mg, 0.18 mmol) w... | 10.6084/m9.figshare.5104873.v1 | null | Primary amide | Nitrile | null | null | c1ccc2ncncc2c1.c1ccccc1 | HO- | ClCCl.CN(C=O)C | -78 | null | CC(C)c1nc2cc(OCc3cccc(F)c3)ccc2c(=O)n1CC(N)=O>ClCCl.CN(C=O)C>CC(C)c1nc2cc(OCc3cccc(F)c3)ccc2c(=O)n1CC#N |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8cdd1682398d44799c23b12882d311f3 | CCOC(=O)CNC.Clc1ccnc(Cl)n1>>CCOC(=O)CN(C)c1nccc(Cl)n1 | ClC1=NC=CC(=N1)Cl.CNCC(=O)OCC.C(C)N(CC)CC>>ClC1=NC(=NC=C1)N(CC(=O)OCC)C | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][NH:7][CH3:8].Cl[c:9]1[n:10][cH:11][cH:12][c:13]([Cl:14])[n:15]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]([CH3:8])[c:9]1[n:10][cH:11][cH:12][c:13]([Cl:14])[n:15]1 | CCOC(=O)CNC.Clc1ccnc(Cl)n1 | CCOC(=O)CN(C)c1nccc(Cl)n1 | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | Ullmann-Goldberg Substitution amine | 8a13b42f4b06102b68f4963e65202071bf1d0630fbad1b11bbd8e99b9f9c8f34 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cncnc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C:6]-[#8:7]-[C:8](=[O;D1;H0:9])-[C:10]-[N;H0;D3;+0:11](-[C;D1;H3:12])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | null | null | null | null | 30.0 g (0.20 mol) of 2,4-dichloropyrimidine, 30.9 g (0.20 mol) of ethyl N-methylglycinate and 61.0 g (0.60 mol) of triethylamine in 200 ml of dioxane are stirred at 50° C. for 10 min. The mixture is filtered off with suction and the mother liquor is concentrated to half the original volume. A solid crystallizes out, wh... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | c1cncnc1 | c1cncnc1 | c1cncnc1 | HCl | O1CCOCC1 | null | null | CCOC(=O)CNC.Clc1ccnc(Cl)n1>O1CCOCC1>CCOC(=O)CN(C)c1nccc(Cl)n1 |
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