dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-067378496b04452e821815e4bd116d99 | CCCCCn1c(=S)[nH]c(=O)c2[nH]c(C(F)(F)F)nc21.COS(=O)(=O)OC>>CCCCCn1c(SC)nc(=O)c2[nH]c(C(F)(F)F)nc21 | C(CCCC)N1C(NC(C=2NC(=NC12)C(F)(F)F)=O)=S.[OH-].[Na+].S(=O)(=O)(OC)OC>>CSC1=NC(C=2NC(=NC2N1CCCCC)C(F)(F)F)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:10][c:11](=[O:12])[c:13]2[nH:14][c:15]([C:16]([F:17])([F:18])[F:19])[n:20][c:21]12.COS(=O)(=O)O[CH3:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]([S:8][CH3:9])[n:10][c:11](=[O:12])[c:13]2[nH:14][c:15]([C:16]([F:17])([F:18])[F:19])[n:20][c:21]12 | CCCCCn1c(=S)[nH]c(=O)c2[nH]c(C(F)(F)F)nc21.COS(=O)(=O)OC | CCCCCn1c(SC)nc(=O)c2[nH]c(C(F)(F)F)nc21 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 0161fed9f1388ec369b7cbafe281cc52a2e7ee362447238b9354e3768807eefa | e73b6e23c9de2770653dfe1c031448ae08eae1a1e8b31e289bfc4b4719e52064 | O=c1nc[nH]c2nc[nH]c12 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[C:2]-[#7;a:3]1:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:2:[c:9](=[O;D1;H0:10]):[nH;D2;+0:11]:[c;H0;D3;+0:12]:1=[S;H0;D1;+0:13]>>[C:2]-[#7;a:3]1:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:2:[c:9](=[O;D1;H0:10]):[n;H0;D2;+0:11]:[c;H0;D3;+0:12]:1-[S;H0;D2;+0:13]-[CH3;D1;+0:1] | 95.6 | [{"value": 95.6, "product": "CSC1=NC(C=2NC(=NC2N1CCCCC)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.7, "product": "CSC1=NC(C=2NC(=NC2N1CCCCC)C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To the solution of 3-pentyl-2-thioxo-8-(trifluoromethyl)-1,2,3,7-tetrahydro-6H-purin-6-one (600 mg, 2 mmol) in a 2 M solution of sodium hydroxide in water (12.0 mL) was added dimethyl sulfate (0.30 mL, 3.2 mmol). The reaction mixture was stirred at room temperature for 1.5 h and quenched with acetic acid. The resulting... | 10.6084/m9.figshare.5104873.v1 | null | Thiocarbonyl | Monosulfide | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HO- | O | null | 1.5 | CCCCCn1c(=S)[nH]c(=O)c2[nH]c(C(F)(F)F)nc21.COS(=O)(=O)OC>O>CCCCCn1c(SC)nc(=O)c2[nH]c(C(F)(F)F)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-838894972a19416c8dc5bca23021abb4 | CCCCCN1c2nc(C(F)(F)F)[nH]c2C(=O)NC1SC.NN>>CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]c(C(F)(F)F)nc21 | CSC1NC(C=2NC(=NC2N1CCCCC)C(F)(F)F)=O.NN>>C(CCCC)N1/C(/NC(C=2NC(=NC12)C(F)(F)F)=O)=N/N | CS[CH:7]1[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:21]2[c:13]([nH:14][c:15]([C:16]([F:17])([F:18])[F:19])[n:20]2)[C:11](=[O:12])[NH:10]1.[NH2:8][NH2:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH2:9])[nH:10][c:11](=[O:12])[c:13]2[nH:14][c:15]([C:16]([F:17])([F:18])[F:19])[n:20][c:21]12 | CCCCCN1c2nc(C(F)(F)F)[nH]c2C(=O)NC1SC.NN | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]c(C(F)(F)F)nc21 | null | null | O | Miscellaneous | OtherReaction | 95e6ec4ef33bb106a3bdb58795cc57ba37baa15165453addc14097b6a24c5025 | 2ba1ac28c36a0747dfaa43d922f0b0fd42ee3ff9c9f7e15186668fec5629e33f | N=c1[nH]c(=O)c2[nH]cnc2[nH]1 | C-S-[CH;D3;+0:1]1-[NH;D2;+0:2]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2-[N;H0;D3;+0:10]-1-[C:11]-[C:12].[N;D1;H2:13]-[NH2;D1;+0:14]>>[C:12]-[C:11]-[n;H0;D3;+0:10]1:[c:9]2:[#7;a:8]:[c:7]:[#7;a:6]:[c:5]:2:[c;H0;D3;+0:3](=[O;D1;H0:4]):[nH;D2;+0:2]/[c;H0;D3;+0:1]:1=[N;H0;D2;+0:14]\[N;D1;H2:13] | 86.5 | [{"value": 65.0, "product": "C(CCCC)N1/C(/NC(C=2NC(=NC12)C(F)(F)F)=O)=N/N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.5, "product": "C(CCCC)N1/C(/NC(C=2NC(=NC12)C(F)(F)F)=O)=N/N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 1 | HOUR | A mixture of 2-(methylthio)-3-pentyl-8-(trifluoromethyl)-1,2,3,7-tetrahydro-6H-purin-6-one (0.61 g, 0.95 mmol), hydrazine (3 mL, 100 mmol) and water (3 mL) was stirred at 100° C. for 1 h. The reaction solution was concentrated under reduced pressure. The residue was dissolved in DMSO and purified by preparative LCMS. T... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Secondary amide.Tertiary amine.Monosulfide | Hydrazone | c1nc2c(n1)[N]CNC2 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | Other | O | 100 | 1 | CCCCCN1c2nc(C(F)(F)F)[nH]c2C(=O)NC1SC.NN>O>CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]c(C(F)(F)F)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7460d3dbb3654fe8ac42ae7a7e072513 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]c(C(F)(F)F)nc21.CCOC(C)(OCC)OCC>>CCCCCn1c2nc(C(F)(F)F)[nH]c2c(=O)n2c(C)nnc12 | C(CCCC)N1/C(/NC(C=2NC(=NC12)C(F)(F)F)=O)=N/N.C(C)(OCC)(OCC)OCC>>CC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)C(F)(F)F)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([C:10]([F:11])([F:12])[F:13])[nH:14][c:15]2[c:16](=[O:17])[nH:18]/[c:23]1=[N:22]\[NH2:21].CCO[C:19](OCC)(OCC)[CH3:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([C:10]([F:11])([F:12])[F:13])[nH:14][c:15]2[c:16](=[O:17])[n:18]2[c:19]([CH3:20])[n:2... | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]c(C(F)(F)F)nc21.CCOC(C)(OCC)OCC | CCCCCn1c2nc(C(F)(F)F)[nH]c2c(=O)n2c(C)nnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ee0085044cada96f0b435a4156edc12d66c02309699c14d468ea3b7289b478ad | d53861995bb64d247d09c3f779c372454b394f82c16bc2582c721d04267c3478 | O=c1c2[nH]cnc2[nH]c2nncn12 | C-C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-O-C-C)-O-C-C.[C:3]-[#7;a:4]1:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10](=[O;D1;H0:11]):[nH;D2;+0:12]/[c;H0;D3;+0:13]:1=[N;H0;D2;+0:14]\[NH2;D1;+0:15]>>[C:3]-[#7;a:4]1:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10](=[O;D1;H0:11]):[n;H0;D3;+0:12]2:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D... | null | [] | null | null | 1 | HOUR | A mixture of (2E)-3-pentyl-8-(trifluoromethyl)-3,7-dihydro-1H-purine-2,6-dione-2-hydrazone (0.020 g, 0.14 mmol) and triethyl orthoacetate (2 mL, 10 mmol) was stirred at room temperature for 1 h. The reaction mixture was concentrated under vacuum and the residue was purified by preparative LCMS. The product fractions we... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ether.Ether.Ether | null | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | HO- | null | null | 1 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]c(C(F)(F)F)nc21.CCOC(C)(OCC)OCC>>CCCCCn1c2nc(C(F)(F)F)[nH]c2c(=O)n2c(C)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7bf8b5b452ce4684a8db2a4c4c018f0c | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]c(C(F)(F)F)nc21>>CCCCCn1c2nc(C(F)(F)F)[nH]c2c(=O)n2cnnc12 | C(CCCC)N1/C(/NC(C=2NC(=NC12)C(F)(F)F)=O)=N/N.C(OCC)(OCC)OCC>>C(CCCC)N1C=2N(C(C=3NC(=NC13)C(F)(F)F)=O)C=NN2 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([C:10]([F:11])([F:12])[F:13])[nH:14][c:15]2[c:16](=[O:17])[nH:18]/[c:22]1=[N:21]\[NH2:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([C:10]([F:11])([F:12])[F:13])[nH:14][c:15]2[c:16](=[O:17])[n:18]2[cH:19][n:20][n:21][c:22]12 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]c(C(F)(F)F)nc21 | CCCCCn1c2nc(C(F)(F)F)[nH]c2c(=O)n2cnnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 60a3d12ea17afaadb59a56b0f52041f740243ef406a6802686b793ec22e80d0f | d627647f8a5758e4c676083258d3a8813f47848ab7ceb334945a07e482fcef85 | O=c1c2[nH]cnc2[nH]c2nncn12 | [C:1]-[#7;a:2]1:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8](=[O;D1;H0:9]):[nH;D2;+0:10]/[c;H0;D3;+0:11]:1=[N;H0;D2;+0:12]\[NH2;D1;+0:13]>>[C:1]-[#7;a:2]1:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8](=[O;D1;H0:9]):[n;H0;D3;+0:10]2:[c:14]:[n;H0;D2;+0:13]:[n;H0;D2;+0:12]:[c;H0;D3;+0:11]:1:2 | 227.3 | [{"value": 48.0, "product": "C(CCCC)N1C=2N(C(C=3NC(=NC13)C(F)(F)F)=O)C=NN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 227.3, "product": "C(CCCC)N1C=2N(C(C=3NC(=NC13)C(F)(F)F)=O)C=NN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of (2E)-3-pentyl-8-(trifluoromethyl)-3,7-dihydro-1H-purine-2,6-dione-2-hydrazone (0.020 g, 0.14 mmol) and triethyl orthoformate (2 mL, 0.01 mol) was stirred at room temperature for 1 h. The reaction mixture was concentrated under vacuum and the residue was purified by preparative LCMS. The product fractions w... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone | null | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | Other | null | null | 1 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]c(C(F)(F)F)nc21>>CCCCCn1c2nc(C(F)(F)F)[nH]c2c(=O)n2cnnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-30172eddcbc441a6ac8a88d2eff42fac | CCCCC=O.NC(=O)c1[nH]cnc1N>>CCCCCNc1nc[nH]c1C(N)=O | NC=1N=CNC1C(=O)N.C(CCCC)=O.C(#N)[BH3-].[Na+]>>C(CCCC)NC=1N=CNC1C(=O)N | O=[CH:5][CH2:4][CH2:3][CH2:2][CH3:1].[NH2:6][c:7]1[n:8][cH:9][nH:10][c:11]1[C:12]([NH2:13])=[O:14]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][c:7]1[n:8][cH:9][nH:10][c:11]1[C:12]([NH2:13])=[O:14] | CCCCC=O.NC(=O)c1[nH]cnc1N | CCCCCNc1nc[nH]c1C(N)=O | null | null | CO | Heteroatom Alkylation and Arylation | Reductive amination with aldehyde | 422be648aea52bce28ccc8fb32ec3178aaa47bbd624f063874619362f075b5f2 | 7915721a3e395aed85e3c40dc4d725c571a931ac517c6a0da16f2a2b0bb5eac7 | c1c[nH]cn1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[N;D1;H2:4]-[C:5](=[O;D1;H0:6])-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:1-[NH2;D1;+0:12]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[NH;D2;+0:12]-[c:11]1:[#7;a:10]:[c:9]:[#7;a:8]:[c:7]:1-[C:5](-[N;D1;H2:4])=[O;D1;H0:6] | 65.7 | [{"value": 63.1, "product": "C(CCCC)NC=1N=CNC1C(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.7, "product": "C(CCCC)NC=1N=CNC1C(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 4-Amino-1H-imidazole-5-carboxamide (13.0 g, 0.104 mol) and valeraldehyde (11 mL, 0.10 mol) were mixed in methanol (200 mL). After being stirred for 30 min, sodium cyanoborohydride (6.5 g, 0.10 mol) was added to the solution and stirring was continued overnight. The reaction mixture was concentrated under reduced pressu... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Secondary amine | null | null | c1c[nH]cn1 | Other | CO | null | 0.5 | CCCCC=O.NC(=O)c1[nH]cnc1N>CO>CCCCCNc1nc[nH]c1C(N)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6998397603674178bb5187b16f13eace | CCCCCNc1nc[nH]c1C(N)=O.O=C(N=C=S)c1ccccc1>>CCCCCN(C(=S)NC(=O)c1ccccc1)c1nc[nH]c1C(N)=O | C(CCCC)NC=1N=CNC1C(=O)N.C(C1=CC=CC=C1)(=O)N=C=S>>C(C1=CC=CC=C1)(=O)NC(=S)N(C=1N=CNC1C(=O)N)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][c:18]1[n:19][cH:20][nH:21][c:22]1[C:23]([NH2:24])=[O:25].[C:7](=[S:8])=[N:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:7](=[S:8])[NH:9][C:10](=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1)[c:18]1[n:19][cH:20][nH... | CCCCCNc1nc[nH]c1C(N)=O.O=C(N=C=S)c1ccccc1 | CCCCCN(C(=S)NC(=O)c1ccccc1)c1nc[nH]c1C(N)=O | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | thiourea | 16b9dd18807f693b1cdd004c800af858aba15692e46e0e83fca1718f8bcadabb | 48e0e6261e922bdea79c78ea511461d733cbd49c10100c782d86c83675c4be7c | O=C(NC(=S)Nc1c[nH]cn1)c1ccccc1 | [C:1]-[C:2]-[NH;D2;+0:3]-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[C:9](-[N;D1;H2:10])=[O;D1;H0:11].[O;D1;H0:12]=[C:13](-[c:14])-[N;H0;D2;+0:15]=[C;H0;D2;+0:16]=[S;D1;H0:17]>>[C:1]-[C:2]-[N;H0;D3;+0:3](-[C;H0;D3;+0:16](=[S;D1;H0:17])-[NH;D2;+0:15]-[C:13](=[O;D1;H0:12])-[c:14])-[c:4]1:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:1-[C:9]... | 139.1 | [{"value": 80.0, "product": "C(C1=CC=CC=C1)(=O)NC(=S)N(C=1N=CNC1C(=O)N)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 139.1, "product": "C(C1=CC=CC=C1)(=O)NC(=S)N(C=1N=CNC1C(=O)N)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of 4-(pentylamino)-1H-imidazole-5-carboxamide (4.0 g, 0.020 mol) in DCM (50 mL) was added benzoyl isothiocyanate (3.3 mL, 0.024 mol). After being stirred overnight, the solid formed was filtered to give the crude product (10 g, ca 60% purity, 80% yield). This product was used for next step without further... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine.Isothiocyanate | Thiourea | null | null | c1ccccc1.c1c[nH]cn1 | null | C(Cl)Cl | null | 8 | CCCCCNc1nc[nH]c1C(N)=O.O=C(N=C=S)c1ccccc1>C(Cl)Cl>CCCCCN(C(=S)NC(=O)c1ccccc1)c1nc[nH]c1C(N)=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4e9d8453a0f47fab13d4cea37fbad55 | CCCCCN(C(=S)NC(=O)c1ccccc1)c1nc[nH]c1C(N)=O>>CCCCCn1c(=S)[nH]c(=O)c2[nH]cnc21 | C(C1=CC=CC=C1)(=O)NC(=S)N(C=1N=CNC1C(=O)N)CCCCC.[OH-].[Na+].Cl>>C(CCCC)N1C(NC(C=2NC=NC12)=O)=S | O=C(N[C:7]([N:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:16]1[c:12]([C:10]([NH2:9])=[O:11])[nH:13][cH:14][n:15]1)=[S:8])c1ccccc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:9][c:10](=[O:11])[c:12]2[nH:13][cH:14][n:15][c:16]12 | CCCCCN(C(=S)NC(=O)c1ccccc1)c1nc[nH]c1C(N)=O | CCCCCn1c(=S)[nH]c(=O)c2[nH]cnc21 | null | null | O | Miscellaneous | OtherReaction | 0252aefeec8e267f50de46810e919c261b4cb308e945d000117b9bcb9d1582e0 | 9e0b04c616da96e0a2af4ca4b9d4b3bbdfbb764c8e3965d78a6a9136f6c866ee | O=c1[nH]c(=S)[nH]c2nc[nH]c12 | O=C(-N-[C;H0;D3;+0:1](=[S;D1;H0:2])-[N;H0;D3;+0:3](-[C:4]-[C:5])-[c:6]1:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:1-[C;H0;D3;+0:11](-[NH2;D1;+0:12])=[O;D1;H0:13])-c1:c:c:c:c:c:1>>[C:5]-[C:4]-[n;H0;D3;+0:3]1:[c:6]2:[#7;a:7]:[c:8]:[#7;a:9]:[c:10]:2:[c;H0;D3;+0:11](=[O;D1;H0:13]):[nH;D2;+0:12]:[c;H0;D3;+0:1]:1=[S;D1;H0:2] | 94 | [{"value": 94.0, "product": "C(CCCC)N1C(NC(C=2NC=NC12)=O)=S", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 4-[[(benzoylamino)carbonothioyl](pentyl)amino]-1H-imidazole-5-carboxamide (11.8 g, 0.0263 mol) and 1 M of sodium hydroxide in water (75 mL) was heated to reflux for 3 h. Solid was formed in the reaction mixture. The reaction mixture was adjusted to pH 3-4 with concentrated HCl with cooling in an ice bath. ... | 10.6084/m9.figshare.5104873.v1 | null | Thiourea.Primary amide.Secondary amide | Thiocarbonyl | c1c[nH]cn1.c1ccccc1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HO- | O | null | null | CCCCCN(C(=S)NC(=O)c1ccccc1)c1nc[nH]c1C(N)=O>O>CCCCCn1c(=S)[nH]c(=O)c2[nH]cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c5affaf43c70471d821746c1e957c5ee | CCCCCn1c(=S)[nH]c(=O)c2[nH]cnc21.NN>>CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21 | C(CCCC)N1C(NC(C=2NC=NC12)=O)=S.NN>>C(CCCC)N1/C(/NC(C=2NC=NC12)=O)=N/N | S=[c:7]1[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:17]2[c:13]([c:11](=[O:12])[nH:10]1)[nH:14][cH:15][n:16]2.[NH2:8][NH2:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH2:9])[nH:10][c:11](=[O:12])[c:13]2[nH:14][cH:15][n:16][c:17]12 | CCCCCn1c(=S)[nH]c(=O)c2[nH]cnc21.NN | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 2e80fee15f068129596c03f86e4a84f3567a03df4d28de9eb824e4b8de606d19 | b31709867bbae7bd190a95c324309111afc274c1ce2b8bd283fc7d83feae5185 | N=c1[nH]c(=O)c2[nH]cnc2[nH]1 | S=[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[#7;a:7]):[#7;a:8]:1-[C:9].[N;D1;H2:10]-[NH2;D1;+0:11]>>[#7;a:5]:[c:4]1:[c:3]:[#7;a:2]/[c;H0;D3;+0:1](=[N;H0;D2;+0:11]\[N;D1;H2:10]):[#7;a:8](-[C:9]):[c:6]:1:[#7;a:7] | 79.4 | [{"value": 78.0, "product": "C(CCCC)N1/C(/NC(C=2NC=NC12)=O)=N/N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.4, "product": "C(CCCC)N1/C(/NC(C=2NC=NC12)=O)=N/N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | 3-Pentyl-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one (6.0 g, 16 mmol) was mixed with hydrazine (10 mL, 300 mmol) and water (10 mL). The mixture was heated at 100° C. for 8 h. The solid formed was filtered and washed with water to give the desired product (3.0 g, 78%). LCMS calculated for C10H17N6O (M+H): 237.1; found: 2... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Thiocarbonyl | Hydrazone | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | Other | O | 100 | null | CCCCCn1c(=S)[nH]c(=O)c2[nH]cnc21.NN>O>CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b8a05952f69a45aab60bfdaad89b588e | CCCCCn1/c(=N\N)[nH]c(=O)c2[nH]cnc21.CCOC(C)(OCC)OCC>>CCCCCn1c2nc[nH]c2c(=O)n2c(C)nnc12 | C(CCCC)N1\C(\NC(C=2NC=NC12)=O)=N/N.C(C)(OCC)(OCC)OCC>>CC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[nH:14]/[c:19]1=[N:18]/[NH2:17].CCO[C:15](OCC)(OCC)[CH3:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15]([CH3:16])[n:17][n:18][c:19]12 | CCCCCn1/c(=N\N)[nH]c(=O)c2[nH]cnc21.CCOC(C)(OCC)OCC | CCCCCn1c2nc[nH]c2c(=O)n2c(C)nnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ee0085044cada96f0b435a4156edc12d66c02309699c14d468ea3b7289b478ad | d53861995bb64d247d09c3f779c372454b394f82c16bc2582c721d04267c3478 | O=c1c2[nH]cnc2[nH]c2nncn12 | C-C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-O-C-C)-O-C-C.[C:3]-[#7;a:4]1:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10](=[O;D1;H0:11]):[nH;D2;+0:12]/[c;H0;D3;+0:13]:1=[N;H0;D2;+0:14]/[NH2;D1;+0:15]>>[C:3]-[#7;a:4]1:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10](=[O;D1;H0:11]):[n;H0;D3;+0:12]2:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D... | 91.6 | [{"value": 91.0, "product": "CC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.6, "product": "CC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A mixture of (2Z)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (3.1 g, 0.013 mol) and triethyl orthoacetate (20 mL, 0.1 mol) was heated at 100° C. for 3 h. The suspension was cooled to room temperature and the solid formed was filtered and washed with DCM/Hex (1:1) mixture to provide the desired product (3.1 g,... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ether.Ether.Ether | null | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | HO- | null | 100 | null | CCCCCn1/c(=N\N)[nH]c(=O)c2[nH]cnc21.CCOC(C)(OCC)OCC>>CCCCCn1c2nc[nH]c2c(=O)n2c(C)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4afcfa8f3a10469d8d887508de74b55c | CCCCCn1c2nc[nH]c2c(=O)n2c(C)nnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(C)nnc12 | CC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O.BrN1C(CCC1=O)=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)C)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH3:17])[n:18][n:19][c:20]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH3:17])[n:18][n:19][c:20]12 | CCCCCn1c2nc[nH]c2c(=O)n2c(C)nnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(C)nnc12 | null | null | C1CCOC1 | Functional Group Interconversion | Bromination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nncn12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | 31 | [{"value": 30.0, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)C)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.0, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)C)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | To a solution of 3-methyl-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (1.0 g, 3.8 mmol) in THF (50 mL) was added N-bromosuccinimide (0.75 g, 4.2 mol). The mixture was heated at 70° C. for 1 h and concentrated in vacuum. The residue was taken up in water and EtOAc. The organic layer was separated and the a... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | HO- | C1CCOC1 | 70 | null | CCCCCn1c2nc[nH]c2c(=O)n2c(C)nnc12.O=C1CCC(=O)N1Br>C1CCOC1>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(C)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-41c9da3ea5ee4f24a7ebb47139cdd6e1 | CCCCCn1c2nc[nH]c2c(=O)n2c(C)nnc12.O=C1CCC(=O)N1Cl>>CCCCCn1c2nc(Cl)[nH]c2c(=O)n2c(C)nnc12 | CC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O.ClN1C(CCC1=O)=O>>ClC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)C)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH3:17])[n:18][n:19][c:20]12.O=C1CCC(=O)N1[Cl:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Cl:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH3:17])[n:18][n:19][c:20]12 | CCCCCn1c2nc[nH]c2c(=O)n2c(C)nnc12.O=C1CCC(=O)N1Cl | CCCCCn1c2nc(Cl)[nH]c2c(=O)n2c(C)nnc12 | null | null | C1CCOC1 | Functional Group Interconversion | Chlorination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nncn12 | O=C1-C-C-C(=O)-N-1-[Cl;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Cl;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | 18.7 | [{"value": 18.7, "product": "ClC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)C)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | To a solution of 3-methyl-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (0.10 g, 0.38 mmol) in THF (5 mL) in a microwave reaction tube was added N-chlorosuccinimide (0.046 g, 0.42 mmol). The mixture was heated at 70° C. in a microwave oven for 20 min. After cooling to room temperature, it was purified using... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | HO- | C1CCOC1 | 70 | null | CCCCCn1c2nc[nH]c2c(=O)n2c(C)nnc12.O=C1CCC(=O)N1Cl>C1CCOC1>CCCCCn1c2nc(Cl)[nH]c2c(=O)n2c(C)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b6a78c8703bf436a8f100acc89ee6a82 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.S=C=S>>CCCCCn1c2nc[nH]c2c(=O)n2c(=S)[nH]nc12 | C(CCCC)N1/C(/NC(C=2NC=NC12)=O)=N/N.C(=S)=S>>C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(NN2)=S | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[nH:14]/[c:19]1=[N:18]\[NH2:17].S=[C:15]=[S:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15](=[S:16])[nH:17][n:18][c:19]12 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.S=C=S | CCCCCn1c2nc[nH]c2c(=O)n2c(=S)[nH]nc12 | null | null | N1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | a709fccbfb10d39ea4751ed4e90ade5fb1f77e1d4eba57b84c8e9008750c73f8 | 1ce3377721e6f0259a08a7073fbf43200481702e7c26234b4a37d6b14b05ec8b | O=c1c2[nH]cnc2[nH]c2n[nH]c(=S)n12 | S=[C;H0;D2;+0:1]=[S;D1;H0:2].[C:3]-[#7;a:4]1:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10](=[O;D1;H0:11]):[nH;D2;+0:12]/[c;H0;D3;+0:13]:1=[N;H0;D2;+0:14]\[NH2;D1;+0:15]>>[C:3]-[#7;a:4]1:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10](=[O;D1;H0:11]):[n;H0;D3;+0:12]2:[c;H0;D3;+0:1](=[S;D1;H0:2]):[nH;D2;+0:15]:[n;H0;D2;+0:1... | 84.9 | [{"value": 84.9, "product": "C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(NN2)=S", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.9, "product": "C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(NN2)=S", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of (2e)-3-pentyl-3,7-dihydro-1h-purine-2,6-dione 2-hydrazone (1.90 g, 8.04 mmol) and carbon disulfide (0.58 ml, 9.64 mmol) in pyridine (30 ml) was stirred at 60° C. for 3 hours. After cooling to room temperature, the solid formed was filtered and dried to yield the desired product (1.90 g, 84.9%). LCMS calcu... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone | Thiocarbonyl | c1ncc2nc[nH]c2n1 | c1nnc2nc3[nH]cnc3cn12 | c1nnc2nc3[nH]cnc3cn12 | Other | N1=CC=CC=C1 | null | null | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.S=C=S>N1=CC=CC=C1>CCCCCn1c2nc[nH]c2c(=O)n2c(=S)[nH]nc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-866471ddd14747758bb510d78607a3e7 | CCCCCn1c2nc[nH]c2c(=O)n2c(=S)[nH]nc12.COS(=O)(=O)OC>>CCCCCn1c2nc[nH]c2c(=O)n2c(SC)nnc12 | C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(NN2)=S.S(=O)(=O)(OC)OC.[OH-].[Na+]>>CSC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15](=[S:16])[nH:18][n:19][c:20]12.COS(=O)(=O)O[CH3:17]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15]([S:16][CH3:17])[n:18][n:19][c:20]12 | CCCCCn1c2nc[nH]c2c(=O)n2c(=S)[nH]nc12.COS(=O)(=O)OC | CCCCCn1c2nc[nH]c2c(=O)n2c(SC)nnc12 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | a0d154c906d5fc14b65e6aea6963ae6fb16e5f2f9a94d6135d5a0f3618d8c6f9 | e73b6e23c9de2770653dfe1c031448ae08eae1a1e8b31e289bfc4b4719e52064 | O=c1c2[nH]cnc2[nH]c2nncn12 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[#7;a:2]:[c:3]1:[c:4]:[#7;a:5]2:[c:6](:[#7;a:7]:[nH;D2;+0:8]:[c;H0;D3;+0:9]:2=[S;H0;D1;+0:10]):[#7;a:11](-[C:12]):[c:13]:1:[#7;a:14]>>[#7;a:2]:[c:3]1:[c:4]:[#7;a:5]2:[c:6](:[#7;a:7]:[n;H0;D2;+0:8]:[c;H0;D3;+0:9]:2-[S;H0;D2;+0:10]-[CH3;D1;+0:1]):[#7;a:11](-[C:12]):[c:13]:1:[#7;a:14] | 85.2 | [{"value": 85.2, "product": "CSC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.1, "product": "CSC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 9-pentyl-3-thioxo-2,3,6,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (1.90 g, 6.83 mmol), dimethyl sulfate (1.03 g, 8.19 mmol) and 1 M of sodium hydroxide in water (25 ml) was stirred at room temperature for 1 hour. The mixture was nutralized to pH=7. The solid formed was filtered and dried to provid... | 10.6084/m9.figshare.5104873.v1 | null | Thiocarbonyl | Monosulfide | c1nnc2nc3[nH]cnc3cn12 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | HO- | O | null | null | CCCCCn1c2nc[nH]c2c(=O)n2c(=S)[nH]nc12.COS(=O)(=O)OC>O>CCCCCn1c2nc[nH]c2c(=O)n2c(SC)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3f08804eadcd404d816d75c6960834c3 | CCCCCn1c2nc[nH]c2c(=O)n2c(SC)nnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(SC)nnc12 | CSC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O.BrN1C(CCC1=O)=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)SC)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([S:17][CH3:18])[n:19][n:20][c:21]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([S:17][CH3:18])[n:19][n:20][c:21]12 | CCCCCn1c2nc[nH]c2c(=O)n2c(SC)nnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(SC)nnc12 | null | null | O.C1CCOC1 | Functional Group Interconversion | Bromination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nncn12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | null | [] | null | null | null | null | A solution of 3-(methylthio)-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (111 mg, 0.380 mmol), N-bromosuccinimide (81.1 mg, 0.456 mmol) in THF (3 ml) was stirred at 70° C. for 3 hours. The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, an... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | HO- | O.C1CCOC1 | null | null | CCCCCn1c2nc[nH]c2c(=O)n2c(SC)nnc12.O=C1CCC(=O)N1Br>O.C1CCOC1>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(SC)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b38acf7db3f4494abf390b4ea925799d | CCCCCn1c2nc[nH]c2c(=O)n2c(S(C)(=O)=O)nnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(S(C)=O)nnc12 | CS(=O)C1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O.CS(=O)(=O)C1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O.BrN1C(CCC1=O)=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)S(=O)C)CCCCC | O=[S:17]([c:16]1[n:15]2[c:13](=[O:14])[c:12]3[c:7]([n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:22]2[n:21][n:20]1)[n:8][cH:9][nH:11]3)([CH3:18])=[O:19].O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([S:17]([CH3:18])=[O:19])[n:20][n:21][... | CCCCCn1c2nc[nH]c2c(=O)n2c(S(C)(=O)=O)nnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(S(C)=O)nnc12 | null | null | O.C1CCOC1 | Miscellaneous | OtherReaction | 6e9a3feacf840bb01f0215e4c654ba2cef799edba173709fc9ea1640b599a3cf | 3481437f31f3a5a13cda2b8d72e1defb69168fe81f49152ff712ff76847d3fa7 | O=c1c2[nH]cnc2[nH]c2nncn12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].O=[S;H0;D4;+0:2](-[C;D1;H3:3])(=[O;D1;H0:4])-[c:5]1:[#7;a:6]:[#7;a:7]:[c:8]2:[#7;a:9]:1:[c:10]:[c:11]1:[#7;a:12]:[cH;D2;+0:13]:[#7;a:14]:[c:15]:1:[#7;a:16]:2-[C:17]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:13]1:[#7;a:12]:[c:11]2:[c:10]:[#7;a:9]3:[c:5](-[S;H0;D3;+0:2](-[C;D1;H3:3])=[O;D1;H0:4]):[#... | null | [] | 70 | CELSIUS | 3 | HOUR | To a mixture of 3-(methylsulfinyl)-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one and 3-(methylsulfonyl)-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (3:2, 125 mg, 0.40 mmol) in THF (3 mL) was added N-bromosuccinimide (82.3 mg, 0.462 mmol). The mixture was stirred at 70° C. for 3 hours. The reac... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide.Sulfone | Aromatic halide.Sulfoxide | c1nc2cn3cn[nH]c3nc2n1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | HO- | O.C1CCOC1 | 70 | 3 | CCCCCn1c2nc[nH]c2c(=O)n2c(S(C)(=O)=O)nnc12.O=C1CCC(=O)N1Br>O.C1CCOC1>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(S(C)=O)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f989cf3c6a7f43c89ff1686e63ed6201 | CCCCCn1/c(=N\N)[nH]c(=O)c2[nH]cnc21.O=C(n1ccnc1)n1ccnc1>>CCCCCn1c2nc[nH]c2c(=O)n2c(O)nnc12 | C(CCCC)N1\C(\NC(C=2NC=NC12)=O)=N/N.C1=CN(C=N1)C(=O)N2C=CN=C2>>OC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[nH:14]/[c:19]1=[N:18]/[NH2:17].c1cn([C:15](n2ccnc2)=[O:16])cn1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15]([OH:16])[n:17][n:18][c:19]12 | CCCCCn1/c(=N\N)[nH]c(=O)c2[nH]cnc21.O=C(n1ccnc1)n1ccnc1 | CCCCCn1c2nc[nH]c2c(=O)n2c(O)nnc12 | null | null | C1CCOC1 | Miscellaneous | OtherReaction | e660c8fc9d528787131eca53d54b66bd3a4a3b51061257fd5d3a800307068f7f | 0c15633fa8e0570ffdf99d6290e749faeaccbf5a6602f8f904bbba80101d7e4d | O=c1c2[nH]cnc2[nH]c2nncn12 | [C:1]-[#7;a:2]1:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8](=[O;D1;H0:9]):[nH;D2;+0:10]/[c;H0;D3;+0:11]:1=[N;H0;D2;+0:12]/[NH2;D1;+0:13].[O;H0;D1;+0:14]=[C;H0;D3;+0:15](-n1:c:c:n:c:1)-n1:c:c:n:c:1>>[C:1]-[#7;a:2]1:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8](=[O;D1;H0:9]):[n;H0;D3;+0:10]2:[c;H0;D3;+0:15](-[OH;D1;+0:14... | 103.7 | [{"value": 98.4, "product": "OC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 103.7, "product": "OC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | A solution of (2z)-3-pentyl-3,7-dihydro-1h-purine-2,6-dione 2-hydrazone (200 mg, 0.846 mmol), N,N-carbonyldiimidazole (1.65 g, 10.2 mmol) in THF (10 ml) was stirred at 70° C. overnight. The reaction mixture was then heated in microwave reactor at 100° C. for 10 min. The reaction was completed checked by LCMS analysis. ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone | Aromatic alcohol | c1ncc2nc[nH]c2n1.c1c[nH]cn1.c1c[nH]cn1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | Other | C1CCOC1 | 100 | null | CCCCCn1/c(=N\N)[nH]c(=O)c2[nH]cnc21.O=C(n1ccnc1)n1ccnc1>C1CCOC1>CCCCCn1c2nc[nH]c2c(=O)n2c(O)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f5ef61842444bd399182df38c7eb900 | CCCCCn1c2nc[nH]c2c(=O)n2c(O)nnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(O)nnc12 | OC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O.BrN1C(CCC1=O)=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([OH:17])[n:18][n:19][c:20]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([OH:17])[n:18][n:19][c:20]12 | CCCCCn1c2nc[nH]c2c(=O)n2c(O)nnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(O)nnc12 | null | null | C1CCOC1 | Functional Group Interconversion | Bromination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nncn12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | null | [] | 70 | CELSIUS | 10 | MINUTE | The mixture of solution of 3-hydroxy-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (100 mg, 0.381 mmol) and N-bromosuccinimide (204 mg, 1.14 mmol) in THF (2 ml) was stirred in a microwave reactor at 70° C. for 10 min. The reaction mixture was filtrated and the filtrate was purified by prep LCMS to yield the... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | HO- | C1CCOC1 | 70 | 0.166667 | CCCCCn1c2nc[nH]c2c(=O)n2c(O)nnc12.O=C1CCC(=O)N1Br>C1CCOC1>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(O)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-17832e53d647405b899d20f820bd49c9 | CCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21>>CCCCn1c2nc[nH]c2c(=O)n2cnnc12 | C(CCC)N1/C(/NC(C=2NC=NC12)=O)=N/N.C(OCC)([O-])[O-]>>C(CCC)N1C=2N(C(C=3NC=NC13)=O)C=NN2 | [CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6]2[n:7][cH:8][nH:9][c:10]2[c:11](=[O:12])[nH:13]/[c:17]1=[N:16]\[NH2:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6]2[n:7][cH:8][nH:9][c:10]2[c:11](=[O:12])[n:13]2[cH:14][n:15][n:16][c:17]12 | CCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21 | CCCCn1c2nc[nH]c2c(=O)n2cnnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 60a3d12ea17afaadb59a56b0f52041f740243ef406a6802686b793ec22e80d0f | d627647f8a5758e4c676083258d3a8813f47848ab7ceb334945a07e482fcef85 | O=c1c2[nH]cnc2[nH]c2nncn12 | [C:1]-[#7;a:2]1:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8](=[O;D1;H0:9]):[nH;D2;+0:10]/[c;H0;D3;+0:11]:1=[N;H0;D2;+0:12]\[NH2;D1;+0:13]>>[C:1]-[#7;a:2]1:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8](=[O;D1;H0:9]):[n;H0;D3;+0:10]2:[c:14]:[n;H0;D2;+0:13]:[n;H0;D2;+0:12]:[c;H0;D3;+0:11]:1:2 | 71.8 | [{"value": 71.8, "product": "C(CCC)N1C=2N(C(C=3NC=NC13)=O)C=NN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 71.8, "product": "C(CCC)N1C=2N(C(C=3NC=NC13)=O)C=NN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | The mixture of (2E)-3-butyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (200 mg, 0.0009 mol) in Ethyl orthoformate (5 mL, 0.03 mol) was heated at 100° C. overnight. After cooling to room temperature, the reaction mixture was filtrated and dried to give the desired product (150 mg, 71.8%). LCMS calculated for C10H13N6O ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone | null | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | Other | null | 100 | null | CCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21>>CCCCn1c2nc[nH]c2c(=O)n2cnnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b140080bbe96414aa828afd3e38d600e | CCCCn1c2nc[nH]c2c(=O)n2cnnc12.O=C1CCC(=O)N1Br>>CCCCn1c2nc(Br)[nH]c2c(=O)n2cnnc12 | C(CCC)N1C=2N(C(C=3NC=NC13)=O)C=NN2.BrN1C(CCC1=O)=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)C=NN3)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6]2[n:7][cH:8][nH:10][c:11]2[c:12](=[O:13])[n:14]2[cH:15][n:16][n:17][c:18]12.O=C1CCC(=O)N1[Br:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6]2[n:7][c:8]([Br:9])[nH:10][c:11]2[c:12](=[O:13])[n:14]2[cH:15][n:16][n:17][c:18]12 | CCCCn1c2nc[nH]c2c(=O)n2cnnc12.O=C1CCC(=O)N1Br | CCCCn1c2nc(Br)[nH]c2c(=O)n2cnnc12 | null | null | C1CCOC1 | Functional Group Interconversion | Bromination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nncn12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | 6 | [{"value": 6.0, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C=NN3)CCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 5.5, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C=NN3)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | To a mixture of 9-butyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (65 mg, 0.28 mmol) in THF (2 mL) was added N-bromosuccinimide (49.8 mg, 0.280 mmol). The mixture was heated in a microwave reactor at 70° C. for 10 minutes. The mixture was purified with prep LCMS to give the desired product (4.8 mg, 6%). LCMS cal... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | HO- | C1CCOC1 | 70 | null | CCCCn1c2nc[nH]c2c(=O)n2cnnc12.O=C1CCC(=O)N1Br>C1CCOC1>CCCCn1c2nc(Br)[nH]c2c(=O)n2cnnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f93cec395f884a94af1db7d40e5ab935 | CCCCn1c2nc[nH]c2c(=O)n2c(CCl)nnc12.CO>>CCCCn1c2nc[nH]c2c(=O)n2c(COC)nnc12 | C(CCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)CCl.CO>>C(CCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)COC | Cl[CH2:15][c:14]1[n:13]2[c:11](=[O:12])[c:10]3[c:6]([n:5]([CH2:4][CH2:3][CH2:2][CH3:1])[c:20]2[n:19][n:18]1)[n:7][cH:8][nH:9]3.[OH:16][CH3:17]>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6]2[n:7][cH:8][nH:9][c:10]2[c:11](=[O:12])[n:13]2[c:14]([CH2:15][O:16][CH3:17])[n:18][n:19][c:20]12 | CCCCn1c2nc[nH]c2c(=O)n2c(CCl)nnc12.CO | CCCCn1c2nc[nH]c2c(=O)n2c(COC)nnc12 | null | null | O.C[O-].[Na+] | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | be62d176246b43d48f94f6bacb3beb02bd17fc7ee5c35751334f4a18453b201e | d4b2af534593ebf4ce27dc032f19c2f57b7f68624a1e46dd4bd7343947c883f4 | O=c1c2[nH]cnc2[nH]c2nncn12 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[#7;a:4]:[c:5](:[#7;a:6]):[#7;a:7]:1:[c:8]:[c:9]:[#7;a:10].[C;D1;H3:11]-[OH;D1;+0:12]>>[#7;a:6]:[c:5]1:[#7;a:4]:[#7;a:3]:[c:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:12]-[C;D1;H3:11]):[#7;a:7]:1:[c:8]:[c:9]:[#7;a:10] | 17.42 | [{"value": 17.42, "product": "C(CCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)COC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 1.1, "product": "C(CCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)COC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | The mixture of 9-butyl-3-(chloromethyl)-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (35 mg, 125 mmol) in 4 M of sodium methoxide in methanol (0.5 mL, 2 mmol) was stirred at room temperature overnight. The reaction mixture was diluted with water and extracted with ethyl acetate three times. The combined organic lay... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Methanol | Ether | null | null | c1nc2cn3cnnc3nc2[nH]1 | HCl | O.C[O-].[Na+] | null | 8 | CCCCn1c2nc[nH]c2c(=O)n2c(CCl)nnc12.CO>O.C[O-].[Na+]>CCCCn1c2nc[nH]c2c(=O)n2c(COC)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f743fbfcea714bceb87d438a56b30efe | CCCCn1c2nc[nH]c2c(=O)n2c(COC)nnc12.O=C1CCC(=O)N1Br>>CCCCn1c2nc(Br)[nH]c2c(=O)n2c(COC)nnc12 | C(CCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)COC.BrN1C(CCC1=O)=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)COC)CCCC | [CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6]2[n:7][cH:8][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15]([CH2:16][O:17][CH3:18])[n:19][n:20][c:21]12.O=C1CCC(=O)N1[Br:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][n:5]1[c:6]2[n:7][c:8]([Br:9])[nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15]([CH2:16][O:17][CH3:18])[n:19][n:20][c:21]12 | CCCCn1c2nc[nH]c2c(=O)n2c(COC)nnc12.O=C1CCC(=O)N1Br | CCCCn1c2nc(Br)[nH]c2c(=O)n2c(COC)nnc12 | null | null | O1CCCC1 | Functional Group Interconversion | Bromination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nncn12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | null | [] | 70 | CELSIUS | 2 | HOUR | The mixture of 9-butyl-3-(methoxymethyl)-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (6 mg, 21.7 mmol), N-bromosuccinimide (4.64 mg, 26.0 mmol) in tetrahydrofuran (10 ml) was stirred at 70° C. for 2 hours. The reaction mixture was concentrated in vacuo and the residue was purified by prep LCMS to yield the desired... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | HO- | O1CCCC1 | 70 | 2 | CCCCn1c2nc[nH]c2c(=O)n2c(COC)nnc12.O=C1CCC(=O)N1Br>O1CCCC1>CCCCn1c2nc(Br)[nH]c2c(=O)n2c(COC)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f990a135d8f4cf0be48933602f2310c | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=Cc1ccccc1>>CCCCCn1/c(=N/N=Cc2ccccc2)[nH]c(=O)c2[nH]cnc21 | C(CCCC)N1/C(/NC(C=2NC=NC12)=O)=N/N.C(C1=CC=CC=C1)=O>>O=C1C=2NC=NC2N(\C(\N1)=N\N=CC1=CC=CC=C1)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH2:9])[nH:17][c:18](=[O:19])[c:20]2[nH:21][cH:22][n:23][c:24]12.O=[CH:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[N:9]=[CH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[nH:17][c:18](=[O:19])[c:20]2[nH:... | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=Cc1ccccc1 | CCCCCn1/c(=N/N=Cc2ccccc2)[nH]c(=O)c2[nH]cnc21 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 369b3f62a39edf615315b2761263eb1b649612c7b3caef083e9b41e01b478de5 | a492f13607987389cdd7ab2f9f1199c71d7d1e56ec2df1828d06f8b8bbe23769 | O=c1[nH]/c(=N\N=Cc2ccccc2)[nH]c2nc[nH]c12 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]/[c:6](=[#7:7]\[NH2;D1;+0:8]):[#7;a:9]>>[#7;a:5]/[c:6](=[#7:7]\[N;H0;D2;+0:8]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4]):[#7;a:9] | null | [] | null | null | null | null | A solution of (2E)-3-pentyl-3,7-dihydro-1h-purine-2,6-dione 2-hydrazone (104 mg, 44 μmol), benzaldehyde (44.7 μl, 44 μmol) in ethanol (10 ml) was stirred at 70° C. for 3 hours. The reaction solution was concentrated in vacuo to give the desired product. LCMS calculated for C17H21N6O(M+H): 325.2; found: 325.2.
Condition... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Aldehyde | null | null | null | c1ccccc1.c1ncc2[nH]cnc2n1 | HO- | C(C)O | null | null | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=Cc1ccccc1>C(C)O>CCCCCn1/c(=N/N=Cc2ccccc2)[nH]c(=O)c2[nH]cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-adfed82200a047a3b3a9bd311002b1ca | CCCCCn1/c(=N/N=Cc2ccccc2)[nH]c(=O)c2[nH]cnc21>>CCCCCn1c2nc[nH]c2c(=O)n2c(-c3ccccc3)nnc12 | O=C1C=2NC=NC2N(\C(\N1)=N\N=CC1=CC=CC=C1)CCCCC>>C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)C2=CC=CC=C2 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[nH:14]/[c:24]1=[N:23]\[N:22]=[CH:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15](-[c:16]3[cH:17][cH:18][cH:19][cH:20][cH:21]3)[n:22... | CCCCCn1/c(=N/N=Cc2ccccc2)[nH]c(=O)c2[nH]cnc21 | CCCCCn1c2nc[nH]c2c(=O)n2c(-c3ccccc3)nnc12 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 066077903128dcf5e3d8c17f71c894783195993eb8e78fea83753934f8800b97 | 42048ba06e684767e79a864f38d2ee087b4547e971032cda3c892dd210eef093 | O=c1c2[nH]cnc2[nH]c2nnc(-c3ccccc3)n12 | [C:1]-[#7;a:2]1:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8](=[O;D1;H0:9]):[nH;D2;+0:10]/[c;H0;D3;+0:11]:1=[N;H0;D2;+0:12]\[N;H0;D2;+0:13]=[CH;D2;+0:14]-[c;H0;D3;+0:15](:[c:16]:[c:17]):[c:18]:[c:19]>>[C:1]-[#7;a:2]1:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8](=[O;D1;H0:9]):[n;H0;D3;+0:10]2:[c;H0;D3;+0:14](-[c;H0;D3;+0... | 22 | [{"value": 22.0, "product": "C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.5, "product": "C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of benzaldehyde [(2E)-6-oxo-3-pentyl-1,3,6,7-tetrahydro-2h-purin-2-ylidene]hydrazone (140 mg, 0.432 mmol) in acetic acid (5 ml) was stirred at 130° C. for 5 hours. The reaction mixture was concentrated in vacuo and purified by prep LCMS to yield the desired product (30 mg, 22% yield). LCMS calculated for C17... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | null | C(C)(=O)O | null | null | CCCCCn1/c(=N/N=Cc2ccccc2)[nH]c(=O)c2[nH]cnc21>C(C)(=O)O>CCCCCn1c2nc[nH]c2c(=O)n2c(-c3ccccc3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-43868b42f769417590b8eda8ca745004 | CCCCCn1c2nc[nH]c2c(=O)n2c(-c3ccccc3)nnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(-c3ccccc3)nnc12 | C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)C2=CC=CC=C2.BrN1C(CCC1=O)=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)C3=CC=CC=C3)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16](-[c:17]3[cH:18][cH:19][cH:20][cH:21][cH:22]3)[n:23][n:24][c:25]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16](-[c:17]3[cH:18][cH:19]... | CCCCCn1c2nc[nH]c2c(=O)n2c(-c3ccccc3)nnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(-c3ccccc3)nnc12 | null | null | C1CCOC1 | Functional Group Interconversion | Bromination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nnc(-c3ccccc3)n12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | 23.3 | [{"value": 23.3, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)C3=CC=CC=C3)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 23.3, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)C3=CC=CC=C3)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 3 | HOUR | To a mixture of 9-pentyl-3-phenyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (30 mg, 0.093 mmol) in THF (30 mL) was added N-bromosuccinimide (19.9 mg, 0.112 mmol). The mixture was stirred at 70° C. for 3 hours. The reaction mixture was concentrated in vacuo and the crude residue was purified using preparative LCM... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | C1CCOC1 | 70 | 3 | CCCCCn1c2nc[nH]c2c(=O)n2c(-c3ccccc3)nnc12.O=C1CCC(=O)N1Br>C1CCOC1>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(-c3ccccc3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-709c6334c03f4f4fac3a9d5d7fe88588 | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(C)nnc12.COc1ccc(CBr)cc1>>CCCCCn1c2nc(Br)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 | BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)C)CCCCC.COC1=CC=C(C=C1)CBr.C([O-])([O-])=O.[K+].[K+]>>BrC1=NC=2N(C=3N(C(C2N1CC1=CC=C(C=C1)OC)=O)C(=NN3)C)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:21]2[c:22](=[O:23])[n:24]2[c:25]([CH3:26])[n:27][n:28][c:29]12.Br[CH2:12][c:13]1[cH:14][cH:15][c:16]([O:17][CH3:18])[cH:19][cH:20]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[n:11]([CH2:12][c:13]3[cH:14][cH:15][c:16]([O... | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(C)nnc12.COc1ccc(CBr)cc1 | CCCCCn1c2nc(Br)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | e7cd22ed9f68e4e320dab4661b2a4d3ee438588eeae829663a94e30f1af40a81 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1c2c(ncn2Cc2ccccc2)[nH]c2nncn12 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[Br;D1;H0:5]-[c:6]1:[#7;a:7]:[c:8]2:[#7;a:9](-[C:10]):[c:11]3:[#7;a:12]:[#7;a:13]:[c:14]:[#7;a:15]:3:[c:16](=[O;D1;H0:17]):[c:18]:2:[nH;D2;+0:19]:1>>[Br;D1;H0:5]-[c:6]1:[#7;a:7]:[c:8]2:[#7;a:9](-[C:10]):[c:11]3:[#7;a:12]:[#7;a:13]:[c:14]:[#7;a:15]:3:[c:16](=[O;D1;H0:17]):[c:18]:2:[n... | 99.7 | [{"value": 99.7, "product": "BrC1=NC=2N(C=3N(C(C2N1CC1=CC=C(C=C1)OC)=O)C(=NN3)C)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.6, "product": "BrC1=NC=2N(C=3N(C(C2N1CC1=CC=C(C=C1)OC)=O)C(=NN3)C)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The mixture of 7-bromo-3-methyl-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (200 mg, 0.59 mmol), 4-methoxyphenyl methylbromide (0.094 mL, 0.65 mmol), potassium carbonate (244 mg, 1.77 mmol) in DMF (10 ml) was stirred at room temperature for 2 hours. The reaction was quenched with water and the solid forme... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HBr | CN(C)C=O | null | 2 | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(C)nnc12.COc1ccc(CBr)cc1>CN(C)C=O>CCCCCn1c2nc(Br)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6f58e20efc344fccad71273b5fb95504 | CCCCCn1c2nc(Br)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nccs1>>CCCCCn1c2nc(-c3nccs3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 | BrC1=NC=2N(C=3N(C(C2N1CC1=CC=C(C=C1)OC)=O)C(=NN3)C)CCCCC.C(CCC)[Sn](C=1SC=CN1)(CCCC)CCCC>>COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)C=4SC=CN4)C=C1 | Br[c:9]1[n:8][c:7]2[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:33]3[n:28]([c:26](=[O:27])[c:25]2[n:15]1[CH2:16][c:17]1[cH:18][cH:19][c:20]([O:21][CH3:22])[cH:23][cH:24]1)[c:29]([CH3:30])[n:31][n:32]3.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c:10]1[n:11][cH:12][cH:13][s:14]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8... | CCCCCn1c2nc(Br)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nccs1 | CCCCCn1c2nc(-c3nccs3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | C1(=CC=CC=C1)C | C-C Coupling | Stille reaction_aryl | af7798868592fdc1fd977df6782021a84f6e702f80fc2b8d53857a20f289b82e | db27eeefac0475c6d74fa10b3167e95a61caaae74e8bbafd45892452c0c3d4d6 | O=c1c2c(nc(-c3nccs3)n2Cc2ccccc2)[nH]c2nncn12 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]):[c:5](:[c:6]:[#7;a:7]):[#7;a:8]:1-[C:9].C-C-C-[CH2]-[Sn](-[CH2]-C-C-C)(-[CH2]-C-C-C)-[c;H0;D3;+0:10]1:[#16;a:11]:[c:12]:[c:13]:[#7;a:14]:1>>[#7;a:7]:[c:6]:[c:5]1:[#7;a:8](-[C:9]):[c;H0;D3;+0:1](-[c;H0;D3;+0:10]2:[#16;a:11]:[c:12]:[c:13]:[#7;a:14]:2):[#7;a:2]:[c:3]:1:[#7;a:4] | 79 | [{"value": 79.0, "product": "COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)C=4SC=CN4)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.4, "product": "COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)C=4SC=CN4)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To the mixture of 7-bromo-6-(4-methoxybenzyl)-3-methyl-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (100 mg, 0.22 mmol), 2-(tributylstannyl)-1,3-thiazole (122 mg, 0.33 mmol) in toluene (14 mL) was added tetrakis(triphenylphosphine)palladium(0) (12.6 mg, 0.011 mmol) under N2. The mixture was refluxed overni... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tin | null | c1nc2cn3cnnc3nc2[nH]1.c1cscn1 | c1cscn1.c1nc2cn3cnnc3nc2[nH]1 | c1cscn1.c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HBr.Sn | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C | null | null | CCCCCn1c2nc(Br)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12.CCC[CH2][Sn]([CH2]CCC)([CH2]CCC)[c]1nccs1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1.C1(=CC=CC=C1)C>CCCCCn1c2nc(-c3nccs3)n(Cc3ccc(OC)cc3)c2c(=... |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d0311d2deb804bcfaafef9a3c35fa535 | CCCCCn1c2nc(-c3nccs3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12>>CCCCCn1c2nc(-c3nccs3)[nH]c2c(=O)n2c(C)nnc12 | COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)C=4SC=CN4)C=C1.FC(C(=O)O)(F)F>>CC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)C=2SC=CN2)=O | COc1ccc(C[n:15]2[c:9](-[c:10]3[n:11][cH:12][cH:13][s:14]3)[n:8][c:7]3[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:24]4[n:19]([c:17](=[O:18])[c:16]32)[c:20]([CH3:21])[n:22][n:23]4)cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9](-[c:10]3[n:11][cH:12][cH:13][s:14]3)[nH:15][c:16]2[c:17](=[O:18])[n:19]2[c:20]... | CCCCCn1c2nc(-c3nccs3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 | CCCCCn1c2nc(-c3nccs3)[nH]c2c(=O)n2c(C)nnc12 | null | null | null | Reduction | OtherReaction | 6db818c9329237f6c02c4e2815db79463314400b1b8bf7ff3388198d85da62cc | 84394d34c591024a84d9393eb3e8adb8ada5a6225c3abafc4dae9aedd4568be4 | O=c1c2[nH]c(-c3nccs3)nc2[nH]c2nncn12 | C-O-c1:c:c:c(-C-[n;H0;D3;+0:1]2:[c:2]3:[c:3](=[O;D1;H0:4]):[#7;a:5]4:[c:6]:[#7;a:7]:[#7;a:8]:[c:9]:4:[#7;a:10](-[C:11]):[c:12]:3:[#7;a:13]:[c:14]:2-[c:15](:[#16;a:16]):[#7;a:17]):c:c:1>>[#16;a:16]:[c:15](-[c:14]1:[#7;a:13]:[c:12]2:[#7;a:10](-[C:11]):[c:9]3:[#7;a:8]:[#7;a:7]:[c:6]:[#7;a:5]:3:[c:3](=[O;D1;H0:4]):[c:2]:2:... | null | [] | 55 | CELSIUS | 8 | HOUR | The mixture of 6-(4-methoxybenzyl)-3-methyl-9-pentyl-7-(1,3-thiazol-2-yl)-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (100 mg, 0.22 mmol) in trifluoroacetic acid (5 mL, 65 mmol) was stirred at 55° C. overnight. The reaction solution was concentrated and purified using preparative LCMS to yield the desired product.... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccccc1.c1nc2nc3nncn3cc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | c1cscn1.c1nc2cn3cnnc3nc2[nH]1 | HO- | null | 55 | 8 | CCCCCn1c2nc(-c3nccs3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12>>CCCCCn1c2nc(-c3nccs3)[nH]c2c(=O)n2c(C)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3cf4c7c27a204d9b926be95f1101ac96 | CCCCCn1c2nc(Br)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12.CSC>>CCCCCn1c2nc(SC)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 | BrC1=NC=2N(C=3N(C(C2N1CC1=CC=C(C=C1)OC)=O)C(=NN3)C)CCCCC.CSC.[Na].C(OC)COC>>COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)SC)C=C1 | Br[c:9]1[n:8][c:7]2[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:30]3[n:25]([c:23](=[O:24])[c:22]2[n:12]1[CH2:13][c:14]1[cH:15][cH:16][c:17]([O:18][CH3:19])[cH:20][cH:21]1)[c:26]([CH3:27])[n:28][n:29]3.C[S:10][CH3:11]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([S:10][CH3:11])[n:12]([CH2:13][c:14]3[cH:15]... | CCCCCn1c2nc(Br)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12.CSC | CCCCCn1c2nc(SC)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 5677a31a24a80ab5ae78fbd186bf6c3ddf719007fef37f4369e52ceb2b94f60e | c58e6934d5c82ddec3b0774dc166fdbb9c9ad3acfbb76cde182cbe53c5c1e68c | O=c1c2c(ncn2Cc2ccccc2)[nH]c2nncn12 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]):[c:5](:[c:6]:[#7;a:7]):[#7;a:8]:1-[C:9].C-[S;H0;D2;+0:10]-[C;D1;H3:11]>>[#7;a:7]:[c:6]:[c:5]1:[#7;a:8](-[C:9]):[c;H0;D3;+0:1](-[S;H0;D2;+0:10]-[C;D1;H3:11]):[#7;a:2]:[c:3]:1:[#7;a:4] | 79.5 | [{"value": 79.5, "product": "COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)SC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.1, "product": "COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)SC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 7-bromo-6-(4-methoxybenzyl)-3-methyl-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (271 mg, 0.6 mmol) and sodium methyl sulfide (45.5 mg, 0.65 mmol) in dimethoxyethane (13.4 ml, 129 mmol) was refluxed for 2 h. The reaction was quenched with water. The solid formed was filtered and dried to yiel... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Monosulfide | Monosulfide | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HBr | null | null | null | CCCCCn1c2nc(Br)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12.CSC>>CCCCCn1c2nc(SC)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-31c63bfb65b549b3bab6aaaa47aade52 | CCCCCn1c2nc(SC)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12>>CCCCCn1c2nc(SC)[nH]c2c(=O)n2c(C)nnc12 | COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)SC)C=C1.FC(C(=O)O)(F)F>>CC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)SC)=O | COc1ccc(C[n:12]2[c:9]([S:10][CH3:11])[n:8][c:7]3[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:21]4[n:16]([c:14](=[O:15])[c:13]32)[c:17]([CH3:18])[n:19][n:20]4)cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([S:10][CH3:11])[nH:12][c:13]2[c:14](=[O:15])[n:16]2[c:17]([CH3:18])[n:19][n:20][c:21]12 | CCCCCn1c2nc(SC)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 | CCCCCn1c2nc(SC)[nH]c2c(=O)n2c(C)nnc12 | null | null | null | Reduction | OtherReaction | 6db818c9329237f6c02c4e2815db79463314400b1b8bf7ff3388198d85da62cc | 84394d34c591024a84d9393eb3e8adb8ada5a6225c3abafc4dae9aedd4568be4 | O=c1c2[nH]cnc2[nH]c2nncn12 | C-O-c1:c:c:c(-C-[n;H0;D3;+0:1]2:[c:2]3:[c:3](=[O;D1;H0:4]):[#7;a:5]4:[c:6]:[#7;a:7]:[#7;a:8]:[c:9]:4:[#7;a:10](-[C:11]):[c:12]:3:[#7;a:13]:[c:14]:2-[#16:15]):c:c:1>>[#16:15]-[c:14]1:[#7;a:13]:[c:12]2:[#7;a:10](-[C:11]):[c:9]3:[#7;a:8]:[#7;a:7]:[c:6]:[#7;a:5]:3:[c:3](=[O;D1;H0:4]):[c:2]:2:[nH;D2;+0:1]:1 | 42 | [{"value": 42.0, "product": "CC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)SC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 0.0, "product": "CC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)SC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of 6-(4-methoxybenzyl)-3-methyl-7-(methylthio)-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (200 mg, 469 mmol) in trifluoroacetic acid (5 ml, 64.9 mmol) was stirred at 55° C. overnight. The solution was concentrated and purified by prep LCMS to yield the desired product (60 mg, 42%). 1HNMR (300 ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccccc1.c1nc2nc3nncn3cc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | HO- | null | null | null | CCCCCn1c2nc(SC)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12>>CCCCCn1c2nc(SC)[nH]c2c(=O)n2c(C)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac740550c70947df9e901a670c8fae98 | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(C)nnc12.OB(O)c1ccccc1>>CCCCCn1c2nc(-c3ccccc3)[nH]c2c(=O)n2c(C)nnc12 | BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)C)CCCCC.C1(=CC=CC=C1)B(O)O.C([O-])([O-])=O.[Na+].[Na+]>>CC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)C2=CC=CC=C2)=O | Br[c:9]1[n:8][c:7]2[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:25]3[n:20]([c:18](=[O:19])[c:17]2[nH:16]1)[c:21]([CH3:22])[n:23][n:24]3.OB(O)[c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9](-[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[nH:16][c:17]2[c:18](=[O:19])[n... | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(C)nnc12.OB(O)c1ccccc1 | CCCCCn1c2nc(-c3ccccc3)[nH]c2c(=O)n2c(C)nnc12 | null | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 | O.COCCOC | C-C Coupling | Suzuki coupling with boronic acids | fba3d7cd2788dca4a8688e3f379e30d3250aa68e83b1dd57d3d04066c5926a02 | 08d2969413ef1a2cd5b43667268ba178160c7b55545bf48018e31f2b019632ec | O=c1c2[nH]c(-c3ccccc3)nc2[nH]c2nncn12 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[c:4]:[#7;a:5]):[c:6](:[#7;a:7]):[#7;a:8]:1.O-B(-O)-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]>>[#7;a:5]:[c:4]:[c:3]1:[#7;a:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:9](:[c:10]:[c:11]):[c:12]:[c:13]):[#7;a:8]:[c:6]:1:[#7;a:7] | 16 | [{"value": 16.0, "product": "CC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)C2=CC=CC=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 15.9, "product": "CC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)C2=CC=CC=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a mixture of 7-bromo-3-methyl-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one (100 mg, 0.30 mmol), phenylboronic acid (39.5 mg, 0.32 mmol), sodium carbonate (100 mg, 0.94 mmol) in water (2 ml) and 1,2-dimethoxyethane (20 ml) was added tetrakis(triphenylphosphine)-palladium(0) (200 mg, 0.10 mmol). The mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic acid | null | c1nc2cn3cnnc3nc2[nH]1.c1ccccc1 | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HBr.B | [Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.COCCOC | null | null | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(C)nnc12.OB(O)c1ccccc1>[Pd].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.O.COCCOC>CCCCCn1c2nc(-c3ccccc3)[nH]c2c(=O)n2c(C)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1d06e169b9be4ce0bc1f293c883e988c | CCCCCn1c2nc(Br)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12.Cn1cc(B2OC(C)(C)C(C)(C)O2)cn1>>CCCCCn1c2nc(-c3cnn(C)c3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 | BrC1=NC=2N(C=3N(C(C2N1CC1=CC=C(C=C1)OC)=O)C(=NN3)C)CCCCC.CN1N=CC(=C1)B1OC(C(O1)(C)C)(C)C.C([O-])([O-])=O.[Na+].[Na+].C1(=CC=CC=C1)C>>COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)C=4C=NN(C4)C)C=C1 | Br[c:9]1[n:8][c:7]2[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:34]3[n:29]([c:27](=[O:28])[c:26]2[n:16]1[CH2:17][c:18]1[cH:19][cH:20][c:21]([O:22][CH3:23])[cH:24][cH:25]1)[c:30]([CH3:31])[n:32][n:33]3.CC1(C)OB([c:10]2[cH:11][n:12][n:13]([CH3:14])[cH:15]2)OC1(C)C>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9... | CCCCCn1c2nc(Br)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12.Cn1cc(B2OC(C)(C)C(C)(C)O2)cn1 | CCCCCn1c2nc(-c3cnn(C)c3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 | null | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | C-C Coupling | Suzuki coupling with boronic esters | 75a5b19ccbb8196367b85ca33ea640e6be14c6fbbd962b8313a6c4a5baf86024 | b42efb3b6a7742d5af594c6a3031e487327e58e9f8c2f428ee68996c98377910 | O=c1c2c(nc(-c3cn[nH]c3)n2Cc2ccccc2)[nH]c2nncn12 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3](:[#7;a:4]):[c:5](:[c:6]:[#7;a:7]):[#7;a:8]:1-[C:9].C-C1(-C)-O-B(-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[#7;a:13](-[C;D1;H3:14]):[c:15]:2)-O-C-1(-C)-C>>[#7;a:7]:[c:6]:[c:5]1:[#7;a:8](-[C:9]):[c;H0;D3;+0:1](-[c;H0;D3;+0:10]2:[c:11]:[#7;a:12]:[#7;a:13](-[C;D1;H3:14]):[c:15]:2):[#7;a:2]:[c:3]:... | 37 | [{"value": 37.0, "product": "COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)C=4C=NN(C4)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 36.2, "product": "COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)C=4C=NN(C4)C)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 7-bromo-6-(4-methoxybenzyl)-3-methyl-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (100 mg, 0.3 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (92 mg, 0.44 mmol) and sat. sodium carbonate (100 mg, 0.9 mmol) in toluene (20 mL, 0.2 mol) was added tetrakis(tripheny... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Boronic ester | null | c1nc2cn3cnnc3nc2[nH]1.B1OCCO1.c1cn[nH]c1 | c1cn[nH]c1.c1nc2cn3cnnc3nc2[nH]1 | c1cn[nH]c1.c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HBr.B | C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1 | null | null | CCCCCn1c2nc(Br)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12.Cn1cc(B2OC(C)(C)C(C)(C)O2)cn1>C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1>CCCCCn1c2nc(-c3cnn(C)c3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c300066a8d043c1b124fce5af14d968 | CCCCCn1c2nc(-c3cnn(C)c3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12>>CCCCCn1c2nc(-c3cnn(C)c3)[nH]c2c(=O)n2c(C)nnc12 | COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)C=4C=NN(C4)C)C=C1>>CC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)C=2C=NN(C2)C)=O | COc1ccc(C[n:16]2[c:9](-[c:10]3[cH:11][n:12][n:13]([CH3:14])[cH:15]3)[n:8][c:7]3[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:25]4[n:20]([c:18](=[O:19])[c:17]32)[c:21]([CH3:22])[n:23][n:24]4)cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9](-[c:10]3[cH:11][n:12][n:13]([CH3:14])[cH:15]3)[nH:16][c:17]2[c:18](=... | CCCCCn1c2nc(-c3cnn(C)c3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 | CCCCCn1c2nc(-c3cnn(C)c3)[nH]c2c(=O)n2c(C)nnc12 | null | null | FC(C(=O)O)(F)F | Reduction | OtherReaction | 6db818c9329237f6c02c4e2815db79463314400b1b8bf7ff3388198d85da62cc | 84394d34c591024a84d9393eb3e8adb8ada5a6225c3abafc4dae9aedd4568be4 | O=c1c2[nH]c(-c3cn[nH]c3)nc2[nH]c2nncn12 | C-O-c1:c:c:c(-C-[n;H0;D3;+0:1]2:[c:2]3:[c:3](=[O;D1;H0:4]):[#7;a:5]4:[c:6]:[#7;a:7]:[#7;a:8]:[c:9]:4:[#7;a:10](-[C:11]):[c:12]:3:[#7;a:13]:[c:14]:2-[c:15]2:[c:16]:[#7;a:17]:[#7;a:18]:[c:19]:2):c:c:1>>[C:11]-[#7;a:10]1:[c:9]2:[#7;a:8]:[#7;a:7]:[c:6]:[#7;a:5]:2:[c:3](=[O;D1;H0:4]):[c:2]2:[nH;D2;+0:1]:[c:14](-[c:15]3:[c:1... | null | [] | null | null | null | null | 6-(4-Methoxybenzyl)-3-methyl-7-(1-methyl-1H-pyrazol-4-yl)-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (50 mg, 0.10 mmol) in trifluoroacetic acid (5 mL) was stirred at 60° C. overnight. The mixture was concentrated, and the residue was purified by preparative LC-MS to give final product. 1HNMR (300 MHz, CD... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccccc1.c1nc2nc3nncn3cc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | c1cn[nH]c1.c1nc2cn3cnnc3nc2[nH]1 | HO- | FC(C(=O)O)(F)F | null | null | CCCCCn1c2nc(-c3cnn(C)c3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12>FC(C(=O)O)(F)F>CCCCCn1c2nc(-c3cnn(C)c3)[nH]c2c(=O)n2c(C)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b664956537524458a430bb8caaff43a3 | CCCCCn1c2nc(Br)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12.c1nc[nH]n1>>CCCCCn1c2nc(-n3cncn3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12.CCCCCn1c2nc(N3CNC=N3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 | BrC1=NC=2N(C=3N(C(C2N1CC1=CC=C(C=C1)OC)=O)C(=NN3)C)CCCCC.[H-].[Na+].N1N=CN=C1>>COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)N4N=CNC4)C=C1.COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)N4N=CN=C4)C=C1 | Br[c:9]1[n:8][c:7]2[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:33]3[n:28]([c:26](=[O:27])[c:25]2[n:15]1[CH2:49][c:50]1[cH:24][cH:23][c:20]([O:21][CH3:22])[cH:11][cH:51]1)[c:62]([CH3:63])[n:64][n:32]3.[nH:10]1[cH:13][n:12][cH:30][n:14]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9](-[n:10]3[cH:11][n:12][cH... | CCCCCn1c2nc(Br)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12.c1nc[nH]n1 | CCCCCn1c2nc(-n3cncn3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12.CCCCCn1c2nc(N3CNC=N3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 7a4a6b8b418bffc2cb8dd40f2d479559bcbdc9c46497f03e81a5b6ac97d96017 | c4af83b1d37521b1334a837db91c273da1aa79a38a5d4c67440b7a63eb68f111 | O=c1c2c(nc(-n3cncn3)n2Cc2ccccc2)[nH]c2nncn12.O=c1c2c(nc(N3CNC=N3)n2Cc2ccccc2)[nH]c2nncn12 | Br-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]2:[#7;a:4](-[C:5]):[c:6]3:[n;H0;D2;+0:7]:[n;H0;D2;+0:8]:[c;H0;D3;+0:9](-[C;D1;H3:10]):[n;H0;D3;+0:11]:3:[c:12](=[O;D1;H0:13]):[c:14]:2:[n;H0;D3;+0:15]:1-[CH2;D2;+0:16]-[c;H0;D3;+0:17]1:[cH;D2;+0:18]:[c:19]:[c;H0;D3;+0:20](-[#8:21]-[C;D1;H3:22]):[cH;D2;+0:23]:[cH;D2;+0:24]:1.[cH;D2;+0:25... | 27.2 | [{"value": 27.2, "product": "COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)N4N=CNC4)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 27.0, "product": "COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)N4N=CN=C4)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Sodium hydride 60% in mineral oil (18 mg, 0.74 mmol) was added to a solution of 1H-1,2,4-Triazole (45 mg, 0.65 mmol) in DMF (10 mL) at room temperature. After stirring for 1 hour at room temperature, 7-bromo-6-(4-methoxybenzyl)-3-methyl-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (200 mg, 0.40 mmol) in DM... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether | Hydrazone.Ether.Ether.Secondary amine | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1.c1nc[nH]n1 | c1nc[nH]n1.c1ccccc1.c1nc2cn3cnnc3nc2[nH]1.C1=N[NH]CN1.c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | c1nc[nH]n1.c1ccccc1.c1nc2cn3cnnc3nc2[nH]1.C1=N[NH]CN1.c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | Br- | CN(C)C=O | null | 1 | CCCCCn1c2nc(Br)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12.c1nc[nH]n1>CN(C)C=O>CCCCCn1c2nc(-n3cncn3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12.CCCCCn1c2nc(N3CNC=N3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cc3352407d79476398c8ef55f2aea4c7 | CCCCCn1c2nc(-n3cncn3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12>>CCCCCn1c2nc(-n3cnnc3)[nH]c2c(=O)n2c(C)nnc12 | COC1=CC=C(CN2C(=NC=3N(C=4N(C(C23)=O)C(=NN4)C)CCCCC)N4N=CN=C4)C=C1>>CC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)N2C=NN=C2)=O | COc1ccc(C[n:15]2[c:9](-[n:10]3[cH:11][n:12][cH:14][n:13]3)[n:8][c:7]3[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:24]4[n:19]([c:17](=[O:18])[c:16]32)[c:20]([CH3:21])[n:22][n:23]4)cc1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9](-[n:10]3[cH:11][n:12][n:13][cH:14]3)[nH:15][c:16]2[c:17](=[O:18])[n:19]2[c:20]... | CCCCCn1c2nc(-n3cncn3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12 | CCCCCn1c2nc(-n3cnnc3)[nH]c2c(=O)n2c(C)nnc12 | null | null | FC(C(=O)O)(F)F | Miscellaneous | OtherReaction | 9330f0fe78a9d21b6520e542495f5a949884a45542318244a9b5052374ef9304 | 291cad8b6dfbbd2c823b5c9d45efc37a166dc3454a9f151ac48cb357f4bc155f | O=c1c2[nH]c(-n3cnnc3)nc2[nH]c2nncn12 | C-O-c1:c:c:c(-C-[n;H0;D3;+0:1]2:[c:2]3:[c:3](=[O;D1;H0:4]):[#7;a:5]4:[c:6]:[#7;a:7]:[#7;a:8]:[c:9]:4:[#7;a:10](-[C:11]):[c:12]:3:[#7;a:13]:[c:14]:2-[n;H0;D3;+0:15]2:[c:16]:[n;H0;D2;+0:17]:[cH;D2;+0:18]:[n;H0;D2;+0:19]:2):c:c:1>>[C:11]-[#7;a:10]1:[c:9]2:[#7;a:8]:[#7;a:7]:[c:6]:[#7;a:5]:2:[c:3](=[O;D1;H0:4]):[c:2]2:[nH;D... | 101.8 | [{"value": 52.0, "product": "CC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)N2C=NN=C2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 101.8, "product": "CC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)N2C=NN=C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 8 | HOUR | A mixture of 6-(4-methoxybenzyl)-3-methyl-9-pentyl-7-(1H-1,2,4-triazol-1-yl)-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (53 mg, 0.12 mmol) in trifluoroacetic acid (10 mL) was stirred at 60° C. overnight. The mixture was concentrated and purified by preparative LC-MS to give the desired product (20 mg, 52%). LCMS ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | null | c1ccccc1.c1nc[nH]n1.c1nc2nc3nncn3cc2[nH]1 | c1nnc[nH]1.c1nc2cn3cnnc3nc2[nH]1 | c1nnc[nH]1.c1nc2cn3cnnc3nc2[nH]1 | HO- | FC(C(=O)O)(F)F | 60 | 8 | CCCCCn1c2nc(-n3cncn3)n(Cc3ccc(OC)cc3)c2c(=O)n2c(C)nnc12>FC(C(=O)O)(F)F>CCCCCn1c2nc(-n3cnnc3)[nH]c2c(=O)n2c(C)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-18959035390142b08c14f23249d9e933 | CCCCCn1c(N)c(N)c(=O)[nH]c1=S.O=C(O)C1CCC1>>CCCCCn1c(NC(=O)C2CCC2)c(N)c(=O)[nH]c1=S | NC=1C(NC(N(C1N)CCCCC)=S)=O.C1(CCC1)C(=O)O.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C)N(CC)CC>>NC1=C(N(C(NC1=O)=S)CCCCC)NC(=O)C1CCC1 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]([NH2:8])[c:15]([NH2:16])[c:17](=[O:18])[nH:19][c:20]1=[S:21].O[C:9](=[O:10])[CH:11]1[CH2:12][CH2:13][CH2:14]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]([NH:8][C:9](=[O:10])[CH:11]2[CH2:12][CH2:13][CH2:14]2)[c:15]([NH2:16])[c:17](=[O:18])[nH:19][c:20]1=[S:21] | CCCCCn1c(N)c(N)c(=O)[nH]c1=S.O=C(O)C1CCC1 | CCCCCn1c(NC(=O)C2CCC2)c(N)c(=O)[nH]c1=S | null | null | O.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1cc(=O)[nH]c(=S)[nH]1)C1CCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C:6]-[#7;a:7]1:[c:8]:[#7;a:9]:[c:10]:[c:11]:[c:12]:1-[NH2;D1;+0:13]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:13]-[c:12]1:[c:11]:[c:10]:[#7;a:9]:[c:8]:[#7;a:7]:1-[C:6])-[C:5] | 83.3 | [{"value": 83.27, "product": "NC1=C(N(C(NC1=O)=S)CCCCC)NC(=O)C1CCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.3, "product": "NC1=C(N(C(NC1=O)=S)CCCCC)NC(=O)C1CCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | The mixture of 5,6-diamino-1-pentyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (1060 mg, 0.00464 mol), cyclobutane carboxylic acid (0.55 g, 5.5 mmol), benzotriazol-1-yloxytris (dimethylamino)phosphonium hexafluorophosphate (2.2 g, 5.1 mmol) and triethylamine (1.3 mL, 9.3 mmol) in DMF (20 mL) was stirred at room temperatur... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1cncnc1.C1CCC1 | HO- | O.CN(C)C=O | null | 4 | CCCCCn1c(N)c(N)c(=O)[nH]c1=S.O=C(O)C1CCC1>O.CN(C)C=O>CCCCCn1c(NC(=O)C2CCC2)c(N)c(=O)[nH]c1=S |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4db92c15687d4904b441c39586a677c2 | CCCCCn1c(NC(=O)C2CCC2)c(N)c(=O)[nH]c1=S>>CCCCCn1c(=S)[nH]c(=O)c2[nH]c(C3CCC3)nc21 | NC1=C(N(C(NC1=O)=S)CCCCC)NC(=O)C1CCC1.[OH-].[Na+]>>C1(CCC1)C1=NC=2N(C(NC(C2N1)=O)=S)CCCCC | O=[C:14]([CH:15]1[CH2:16][CH2:17][CH2:18]1)[NH:19][c:20]1[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:7](=[S:8])[nH:9][c:10](=[O:11])[c:12]1[NH2:13]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:9][c:10](=[O:11])[c:12]2[nH:13][c:14]([CH:15]3[CH2:16][CH2:17][CH2:18]3)[n:19][c:20]12 | CCCCCn1c(NC(=O)C2CCC2)c(N)c(=O)[nH]c1=S | CCCCCn1c(=S)[nH]c(=O)c2[nH]c(C3CCC3)nc21 | null | null | O.CO | Aromatic Heterocycle Formation | OtherReaction | 89fa7eaac6a1bd77ac00b2a959bf2d3cfa13bace835949115b1d4cbc9d1a95d8 | a079090652d9d6c0e17c70eeab94f6d7afea064f52cf5fa9036d5feedd14143a | O=c1[nH]c(=S)[nH]c2nc(C3CCC3)[nH]c12 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[c:3]1:[#7;a:4](-[C:5]):[c:6]:[#7;a:7]:[c:8](=[O;D1;H0:9]):[c:10]:1-[NH2;D1;+0:11])-[C:12](-[C:13])-[C:14]>>[C:13]-[C:12](-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c:3]2:[#7;a:4](-[C:5]):[c:6]:[#7;a:7]:[c:8](=[O;D1;H0:9]):[c:10]:2:[nH;D2;+0:11]:1)-[C:14] | 74.3 | [{"value": 73.7, "product": "C1(CCC1)C1=NC=2N(C(NC(C2N1)=O)=S)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.3, "product": "C1(CCC1)C1=NC=2N(C(NC(C2N1)=O)=S)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 1 | HOUR | The mixture of N-(5-amino-6-oxo-3-pentyl-2-thioxo-1,2,3,6-tetrahydropyrimidin-4-yl)cyclobutanecarboxamide (720 mg, 2.3 mmol) and 2.5 M of sodium hydroxide in water (25 mL) and methanol (25 mL) was stirred at 70° C. for 1 hour. After cooling to room temperature, the reaction mixture was concentrated to remove methanol a... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide.Primary amine | null | c1cncnc1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1CCC1 | HO- | O.CO | 70 | 1 | CCCCCn1c(NC(=O)C2CCC2)c(N)c(=O)[nH]c1=S>O.CO>CCCCCn1c(=S)[nH]c(=O)c2[nH]c(C3CCC3)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e83e9624388e4ca09eb26cca5f7fb850 | CCCCCn1c(=S)[nH]c(=O)c2[nH]c(C3CCC3)nc21.NN>>CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]c(C3CCC3)nc21 | C1(CCC1)C1=NC=2N(C(NC(C2N1)=O)=S)CCCCC.NN>>C1(CCC1)C1=NC=2N(/C(/NC(C2N1)=O)=N/N)CCCCC | S=[c:7]1[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:21]2[c:13]([c:11](=[O:12])[nH:10]1)[nH:14][c:15]([CH:16]1[CH2:17][CH2:18][CH2:19]1)[n:20]2.[NH2:8][NH2:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH2:9])[nH:10][c:11](=[O:12])[c:13]2[nH:14][c:15]([CH:16]3[CH2:17][CH2:18][CH2:19]3)[n:20][c:21]12 | CCCCCn1c(=S)[nH]c(=O)c2[nH]c(C3CCC3)nc21.NN | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]c(C3CCC3)nc21 | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | 2e80fee15f068129596c03f86e4a84f3567a03df4d28de9eb824e4b8de606d19 | b31709867bbae7bd190a95c324309111afc274c1ce2b8bd283fc7d83feae5185 | N=c1[nH]c(=O)c2[nH]c(C3CCC3)nc2[nH]1 | S=[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[#7;a:7]):[#7;a:8]:1-[C:9].[N;D1;H2:10]-[NH2;D1;+0:11]>>[#7;a:5]:[c:4]1:[c:3]:[#7;a:2]/[c;H0;D3;+0:1](=[N;H0;D2;+0:11]\[N;D1;H2:10]):[#7;a:8](-[C:9]):[c:6]:1:[#7;a:7] | 38.6 | [{"value": 38.6, "product": "C1(CCC1)C1=NC=2N(/C(/NC(C2N1)=O)=N/N)CCCCC", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 8 | HOUR | The mixture of 8-cyclobutyl-3-pentyl-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one (0.6 g, 2.0 mmol) in 20 M of hydrazine in water (20 mL) was stirred at 100° C. overnight. After cooling to room temperature, the solid formed was filtered and dried Cooled down, the solid was isolated to give yield the desired product (230 ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Thiocarbonyl | Hydrazone | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1.C1CCC1 | Other | O | 100 | 8 | CCCCCn1c(=S)[nH]c(=O)c2[nH]c(C3CCC3)nc21.NN>O>CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]c(C3CCC3)nc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-02fce3d897b644f7a805e0f7abcf415d | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]c(C3CCC3)nc21.CCOC(C)(OCC)OCC>>CCCCCn1c2nc(C3CCC3)[nH]c2c(=O)n2c(C)nnc12 | C1(CCC1)C1=NC=2N(/C(/NC(C2N1)=O)=N/N)CCCCC.C(C)(OCC)(OCC)OCC>>C1(CCC1)C1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)C)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([CH:10]3[CH2:11][CH2:12][CH2:13]3)[nH:14][c:15]2[c:16](=[O:17])[nH:18]/[c:23]1=[N:22]\[NH2:21].CCO[C:19](OCC)(OCC)[CH3:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([CH:10]3[CH2:11][CH2:12][CH2:13]3)[nH:14][c:15]2[c:16](=[O:17])[n:18]2[c:19]([CH... | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]c(C3CCC3)nc21.CCOC(C)(OCC)OCC | CCCCCn1c2nc(C3CCC3)[nH]c2c(=O)n2c(C)nnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | ee0085044cada96f0b435a4156edc12d66c02309699c14d468ea3b7289b478ad | d53861995bb64d247d09c3f779c372454b394f82c16bc2582c721d04267c3478 | O=c1c2[nH]c(C3CCC3)nc2[nH]c2nncn12 | C-C-O-[C;H0;D4;+0:1](-[C;D1;H3:2])(-O-C-C)-O-C-C.[C:3]-[#7;a:4]1:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10](=[O;D1;H0:11]):[nH;D2;+0:12]/[c;H0;D3;+0:13]:1=[N;H0;D2;+0:14]\[NH2;D1;+0:15]>>[C:3]-[#7;a:4]1:[c:5]2:[#7;a:6]:[c:7]:[#7;a:8]:[c:9]:2:[c:10](=[O;D1;H0:11]):[n;H0;D3;+0:12]2:[c;H0;D3;+0:1](-[C;D1;H3:2]):[n;H0;D... | 10.6 | [{"value": 9.2, "product": "C1(CCC1)C1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)C)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.6, "product": "C1(CCC1)C1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)C)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 8 | HOUR | (2E)-8-cyclobutyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (100 mg, 0.0003 mol) was mixed with triethyl orthoacetate (10 mL, 0.05 mol) and then stirred at 100° C. overnight. After cooling to room temperature, the mixture was concentrated and purified by preparative LCMS to yield the desired product (10 mg, ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Ether.Ether.Ether | null | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | C1CCC1.c1nc2cn3cnnc3nc2[nH]1 | HO- | null | 100 | 8 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]c(C3CCC3)nc21.CCOC(C)(OCC)OCC>>CCCCCn1c2nc(C3CCC3)[nH]c2c(=O)n2c(C)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b4b8f3b3b8e9463da4c1ee9cefd4abea | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.CCN(CC)CC.O=C(O)Cc1ccccc1>>CCCCCn1/c(=N/NC(=O)Cc2ccc(OC)cc2)[nH]c(=O)c2[nH]cnc21 | C(CCCC)N1/C(/NC(C=2NC=NC12)=O)=N/N.C1(=CC=CC=C1)CC(=O)O.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C)N(CC)CC.CN(C)C=O>>COC1=CC=C(C=C1)CC(=O)N/N=C/1\NC(C=2NC=NC2N1CCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH2:9])[nH:21][c:22](=[O:23])[c:24]2[nH:25][cH:26][n:27][c:28]12.CCN(CC)C[CH3:18].[C:10](=[O:11])([CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:19][cH:20]1)[OH:17]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH:9][C:10](=[O:11])[CH2:12][c:13]2[cH:14][cH:15]... | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.CCN(CC)CC.O=C(O)Cc1ccccc1 | CCCCCn1/c(=N/NC(=O)Cc2ccc(OC)cc2)[nH]c(=O)c2[nH]cnc21 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 177253170fc482b4e8e53bbe93fc6da9db18600b85c384afc8c6547566a96f38 | 155f73ccd5cde6fa5b50e1e66b5a06760a53ee9372b42be6acd835f86ba6fca8 | O=C(Cc1ccccc1)N/N=c1\[nH]c(=O)c2[nH]cnc2[nH]1 | C-C-N(-C-C)-C-[CH3;D1;+0:1].[#7;a:2]/[c:3](=[#7:4]\[NH2;D1;+0:5]):[#7;a:6].[O;D1;H0:7]=[C;H0;D3;+0:8](-[OH;D1;+0:9])-[C:10]-[c:11]1:[c:12]:[c:13]:[cH;D2;+0:14]:[c:15]:[c:16]:1>>[#7;a:2]/[c:3](=[#7:4]\[NH;D2;+0:5]-[C;H0;D3;+0:8](=[O;D1;H0:7])-[C:10]-[c:11]1:[c:12]:[c:13]:[c;H0;D3;+0:14](-[O;H0;D2;+0:9]-[CH3;D1;+0:1]):[c... | 98 | [{"value": 98.0, "product": "COC1=CC=C(C=C1)CC(=O)N/N=C/1\\NC(C=2NC=NC2N1CCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | The mixture of (2E)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (0.30 g, 1.3 mmol), benzeneacetic acid, 4-methoxy-(0.23 g, 1.4 mmol), benzotriazol-1-yloxytris-(dimethylamino)phosphonium hexafluorophosphate (0.62 g, 1.40 mmol) and triethylamine (0.53 mL, 3.8 mmol) in DMF (10 mL) were stirred at room temperature... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Carboxylic acid.Tertiary amine | Hydrazone amide.Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ncc2[nH]cnc2n1 | Other | C(C)(=O)OCC | null | 8 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.CCN(CC)CC.O=C(O)Cc1ccccc1>C(C)(=O)OCC>CCCCCn1/c(=N/NC(=O)Cc2ccc(OC)cc2)[nH]c(=O)c2[nH]cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ebfc599309aa403ea7c07a239ca90ee4 | CCCCCn1/c(=N/NC(=O)Cc2ccc(OC)cc2)[nH]c(=O)c2[nH]cnc21>>CCCCCn1c2nc[nH]c2c(=O)n2c(Cc3ccc(OC)cc3)nnc12 | COC1=CC=C(C=C1)CC(=O)N/N=C/1\NC(C=2NC=NC2N1CCCCC)=O>>COC1=CC=C(CC2=NN=C3N2C(C=2NC=NC2N3CCCCC)=O)C=C1 | O=[C:15]([CH2:16][c:17]1[cH:18][cH:19][c:20]([O:21][CH3:22])[cH:23][cH:24]1)[NH:25]/[N:26]=[c:27]1/[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[nH:14]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15]([CH2:16][c:17]3[cH:18]... | CCCCCn1/c(=N/NC(=O)Cc2ccc(OC)cc2)[nH]c(=O)c2[nH]cnc21 | CCCCCn1c2nc[nH]c2c(=O)n2c(Cc3ccc(OC)cc3)nnc12 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | f919762557f16e8feb47c1fb62f203cd1ec4ed5f009cf276d2d0e0ec84ef6b80 | 78b0616e5760c6d4dadfc1fac5c58c0254d0dc7b1bf102fea4bc1349928b0776 | O=c1c2[nH]cnc2[nH]c2nnc(Cc3ccccc3)n12 | O=[C;H0;D3;+0:1](-[C:2]-[c:3])-[NH;D2;+0:4]/[N;H0;D2;+0:5]=[c;H0;D3;+0:6]1\[nH;D2;+0:7]:[c:8](=[O;D1;H0:9]):[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:2:[#7;a:15]:1-[C:16]>>[C:16]-[#7;a:15]1:[c:14]2:[#7;a:13]:[c:12]:[#7;a:11]:[c:10]:2:[c:8](=[O;D1;H0:9]):[n;H0;D3;+0:7]2:[c;H0;D3;+0:1](-[C:2]-[c:3]):[n;H0;D2;+0:4]:[n;H0;... | 95.5 | [{"value": 92.0, "product": "COC1=CC=C(CC2=NN=C3N2C(C=2NC=NC2N3CCCCC)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.5, "product": "COC1=CC=C(CC2=NN=C3N2C(C=2NC=NC2N3CCCCC)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The mixture of 2-(4-methoxyphenyl)-N′-[(2E)-6-oxo-3-pentyl-1,3,6,7-tetrahydro-2H-purin-2-ylidene]acetohydrazide (0.66 g, 1.4 mmol) in toluene (30 mL) was refluxed overnight. The reaction mixture was concentrated to give the crude product as a solid. The solid was washed with ethyl acetate and dried to yield the desired... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide | null | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | C1(=CC=CC=C1)C | null | null | CCCCCn1/c(=N/NC(=O)Cc2ccc(OC)cc2)[nH]c(=O)c2[nH]cnc21>C1(=CC=CC=C1)C>CCCCCn1c2nc[nH]c2c(=O)n2c(Cc3ccc(OC)cc3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-31e62738613d44b7b8ed22acef337079 | CCCCCn1c2nc[nH]c2c(=O)n2c(Cc3ccc(OC)cc3)nnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(Cc3ccc(OC)cc3)nnc12 | COC1=CC=C(CC2=NN=C3N2C(C=2NC=NC2N3CCCCC)=O)C=C1.BrN1C(CCC1=O)=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CC3=CC=C(C=C3)OC)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH2:17][c:18]3[cH:19][cH:20][c:21]([O:22][CH3:23])[cH:24][cH:25]3)[n:26][n:27][c:28]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16](... | CCCCCn1c2nc[nH]c2c(=O)n2c(Cc3ccc(OC)cc3)nnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(Cc3ccc(OC)cc3)nnc12 | null | null | C1CCOC1 | Functional Group Interconversion | Bromination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nnc(Cc3ccccc3)n12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | 60 | [{"value": 60.0, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CC3=CC=C(C=C3)OC)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.2, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CC3=CC=C(C=C3)OC)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 1 | HOUR | To the solution of 3-(4-methoxybenzyl)-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (0.40 g, 1.1 mmol) in THF was added N-Bromosuccinimide (0.29 g, 1.6 mmol). The mixture was stirred at 70° C. for 1 hour. The mixture was concentrated and purified by preparative LCMS to yield the desired product (290 mg, 60... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | C1CCOC1 | 70 | 1 | CCCCCn1c2nc[nH]c2c(=O)n2c(Cc3ccc(OC)cc3)nnc12.O=C1CCC(=O)N1Br>C1CCOC1>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(Cc3ccc(OC)cc3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f9451da4e3474c65a1cbec94728e8aa2 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)Cc1cccc(Br)c1>>CCCCCn1/c(=N/NC(=O)Cc2cccc(Br)c2)[nH]c(=O)c2[nH]cnc21 | C(CCCC)N1/C(/NC(C=2NC=NC12)=O)=N/N.BrC=1C=C(C=CC1)CC(=O)O.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C)N(CC)CC>>BrC=1C=C(C=CC1)CC(=O)N/N=C/1\NC(C=2NC=NC2N1CCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH2:9])[nH:20][c:21](=[O:22])[c:23]2[nH:24][cH:25][n:26][c:27]12.O[C:10](=[O:11])[CH2:12][c:13]1[cH:14][cH:15][cH:16][c:17]([Br:18])[cH:19]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH:9][C:10](=[O:11])[CH2:12][c:13]2[cH:14][cH:15][cH:16][c:17]([Br... | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)Cc1cccc(Br)c1 | CCCCCn1/c(=N/NC(=O)Cc2cccc(Br)c2)[nH]c(=O)c2[nH]cnc21 | null | null | CN(C)C=O.CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | e50d935ef072f0718d4e131af3df793f26e2f0a63884801973739584ab6e55ba | 2740512737e2508c1c8d407d0ee271fd1e1c46ad16223e8e2fc1e12936af0dea | O=C(Cc1ccccc1)N/N=c1\[nH]c(=O)c2[nH]cnc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4].[#7;a:5]/[c:6](=[#7:7]\[NH2;D1;+0:8]):[#7;a:9]>>[#7;a:5]/[c:6](=[#7:7]\[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4]):[#7;a:9] | 78.2 | [{"value": 78.2, "product": "BrC=1C=C(C=CC1)CC(=O)N/N=C/1\\NC(C=2NC=NC2N1CCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.3, "product": "BrC=1C=C(C=CC1)CC(=O)N/N=C/1\\NC(C=2NC=NC2N1CCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | The mixture of (2E)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (0.30 g, 1.3 mmol), (3-bromophenyl)acetic acid (0.30 g, 1.4 mmol), benzotriazol-1-yloxytris-(dimethylamino)phosphonium hexafluorophosphate (0.62 g, 1.4 mol) and triethylamine (0.53 mL, 3.8 mmol) in DMF (10 mL) were stirred at rt overnight. The rea... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Carboxylic acid | Hydrazone amide | null | null | c1ccccc1.c1ncc2[nH]cnc2n1 | HO- | CN(C)C=O.CCOC(=O)C | null | 8 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)Cc1cccc(Br)c1>CN(C)C=O.CCOC(=O)C>CCCCCn1/c(=N/NC(=O)Cc2cccc(Br)c2)[nH]c(=O)c2[nH]cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4e5bf53bb28f4121bbf96a56543d181d | CCCCCn1/c(=N/NC(=O)Cc2cccc(Br)c2)[nH]c(=O)c2[nH]cnc21>>CCCCCn1c2nc[nH]c2c(=O)n2c(Cc3cccc(Br)c3)nnc12 | BrC=1C=C(C=CC1)CC(=O)N/N=C/1\NC(C=2NC=NC2N1CCCCC)=O>>BrC=1C=C(CC2=NN=C3N2C(C=2NC=NC2N3CCCCC)=O)C=CC1 | O=[C:15]([CH2:16][c:17]1[cH:18][cH:19][cH:20][c:21]([Br:22])[cH:23]1)[NH:24]/[N:25]=[c:26]1/[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[nH:14]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15]([CH2:16][c:17]3[cH:18][cH:19]... | CCCCCn1/c(=N/NC(=O)Cc2cccc(Br)c2)[nH]c(=O)c2[nH]cnc21 | CCCCCn1c2nc[nH]c2c(=O)n2c(Cc3cccc(Br)c3)nnc12 | null | null | C1=CC=CC=C1 | Aromatic Heterocycle Formation | OtherReaction | f919762557f16e8feb47c1fb62f203cd1ec4ed5f009cf276d2d0e0ec84ef6b80 | 78b0616e5760c6d4dadfc1fac5c58c0254d0dc7b1bf102fea4bc1349928b0776 | O=c1c2[nH]cnc2[nH]c2nnc(Cc3ccccc3)n12 | O=[C;H0;D3;+0:1](-[C:2]-[c:3])-[NH;D2;+0:4]/[N;H0;D2;+0:5]=[c;H0;D3;+0:6]1\[nH;D2;+0:7]:[c:8](=[O;D1;H0:9]):[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:2:[#7;a:15]:1-[C:16]>>[C:16]-[#7;a:15]1:[c:14]2:[#7;a:13]:[c:12]:[#7;a:11]:[c:10]:2:[c:8](=[O;D1;H0:9]):[n;H0;D3;+0:7]2:[c;H0;D3;+0:1](-[C:2]-[c:3]):[n;H0;D2;+0:4]:[n;H0;... | 86 | [{"value": 86.0, "product": "BrC=1C=C(CC2=NN=C3N2C(C=2NC=NC2N3CCCCC)=O)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The mixture of 2-(3-bromophenyl)-N′-[(2E)-6-oxo-3-pentyl-1,3,6,7-tetrahydro-2H-purin-2-ylidene]acetohydrazide (1.8 g, 4.2 mmol) in benzene (100 mL) was refluxed overnight. The reaction mixture was concentrated to give the desired product 1.5 g. LCMS calculated for C18H20BrN6O (M+H): 415.1; found: 415.1.
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide | null | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | C1=CC=CC=C1 | null | null | CCCCCn1/c(=N/NC(=O)Cc2cccc(Br)c2)[nH]c(=O)c2[nH]cnc21>C1=CC=CC=C1>CCCCCn1c2nc[nH]c2c(=O)n2c(Cc3cccc(Br)c3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa37744ffd204ae0bda5eb08decedb0f | CCCCCn1c2nc[nH]c2c(=O)n2c(Cc3cccc(Br)c3)nnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(Cc3cccc(Br)c3)nnc12 | BrC=1C=C(CC2=NN=C3N2C(C=2NC=NC2N3CCCCC)=O)C=CC1.BrN1C(CCC1=O)=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CC3=CC(=CC=C3)Br)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH2:17][c:18]3[cH:19][cH:20][cH:21][c:22]([Br:23])[cH:24]3)[n:25][n:26][c:27]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH2:17... | CCCCCn1c2nc[nH]c2c(=O)n2c(Cc3cccc(Br)c3)nnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(Cc3cccc(Br)c3)nnc12 | null | null | O1CCCC1 | Functional Group Interconversion | Bromination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nnc(Cc3ccccc3)n12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | 60.7 | [{"value": 60.0, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CC3=CC(=CC=C3)Br)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.7, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CC3=CC(=CC=C3)Br)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 1 | HOUR | To the solution of 3-(3-bromobenzyl)-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (210 mg, 0.50 mmol) in tetrahydrofuran (20 mL) was added N-bromosuccinimide (140 mg, 0.00076 mol). The mixture was stirred at 70° C. for 1 hour. The reaction mixture was concentrated and the residue was purified by preparativ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | O1CCCC1 | 70 | 1 | CCCCCn1c2nc[nH]c2c(=O)n2c(Cc3cccc(Br)c3)nnc12.O=C1CCC(=O)N1Br>O1CCCC1>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(Cc3cccc(Br)c3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cc02c5609ee940d09db25e8d72d847db | CCCCCn1/c(=N\N)[nH]c(=O)c2[nH]cnc21.C[N+](C)=C(Cl)Cl>>CCCCCn1c2nc[nH]c2c(=O)n2c(N(C)C)nnc12 | [Cl-].ClC(=[N+](C)C)Cl.C(CCCC)N1\C(\NC(C=2NC=NC12)=O)=N/N>>CN(C1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O)C | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[nH:14]/[c:21]1=[N:20]/[NH2:19].Cl[C:15](Cl)=[N+:16]([CH3:17])[CH3:18]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15]([N:16]([CH3:17])[CH3:18])[n:19][n:20][c:21]12 | CCCCCn1/c(=N\N)[nH]c(=O)c2[nH]cnc21.C[N+](C)=C(Cl)Cl | CCCCCn1c2nc[nH]c2c(=O)n2c(N(C)C)nnc12 | null | null | C(Cl)Cl | Aromatic Heterocycle Formation | OtherReaction | bbdcadb4c7f8309b13790d502223b759d07ee6c6b4a016cb8f5b21ea1012907e | 8beb4c10f543b2f2f9ecc23edd744a3451fefe5b77680fd9750f8079fceae275 | O=c1c2[nH]cnc2[nH]c2nncn12 | Cl-[C;H0;D3;+0:1](-Cl)=[N+;H0;D3:2](-[C;D1;H3:3])-[C;D1;H3:4].[C:5]-[#7;a:6]1:[c:7]2:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:2:[c:12](=[O;D1;H0:13]):[nH;D2;+0:14]/[c;H0;D3;+0:15]:1=[N;H0;D2;+0:16]/[NH2;D1;+0:17]>>[C:5]-[#7;a:6]1:[c:7]2:[#7;a:8]:[c:9]:[#7;a:10]:[c:11]:2:[c:12](=[O;D1;H0:13]):[n;H0;D3;+0:14]2:[c;H0;D3;+0:1](-[N;... | 69.1 | [{"value": 69.0, "product": "CN(C1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.1, "product": "CN(C1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To methylene chloride (10 mL) was added [B] N-(dichloromethylene)-N-methylmethanaminium chloride (0.21 g, 1.3 mmol). After stirring for 5 mins, (2Z)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (0.10 g, 0.42 mmol) was added, and the mixture was stirred at rt for 5 hrs. LCMS analysis showed product as a major pe... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Alkenyl halide.Alkenyl halide | Tertiary amine | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | HCl | C(Cl)Cl | null | 0.083333 | CCCCCn1/c(=N\N)[nH]c(=O)c2[nH]cnc21.C[N+](C)=C(Cl)Cl>C(Cl)Cl>CCCCCn1c2nc[nH]c2c(=O)n2c(N(C)C)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a8a45e809d9c4e0aa684e3d357ae4db1 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)C(F)(F)F>>CCCCCn1c2nc[nH]c2c(=O)n2c(C(F)(F)F)nnc12 | C(CCCC)N1/C(/NC(C=2NC=NC12)=O)=N/N.FC(C(=O)O)(F)F>>C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)C(F)(F)F | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[nH:14]/[c:22]1=[N:21]\[NH2:20].O=[C:15](O)[C:16]([F:17])([F:18])[F:19]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15]([C:16]([F:17])([F:18])[F:19])[n:20][n:21][c:22]12 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)C(F)(F)F | CCCCCn1c2nc[nH]c2c(=O)n2c(C(F)(F)F)nnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 31291cc3561946553fa0a412aac17e231d5f14813122f81265617512be0c5c26 | a5b6f2cd9527773fa0ccce3fdf3fdb3e48f4277fe83d66b7b9adab2dd2a35cef | O=c1c2[nH]cnc2[nH]c2nncn12 | O-[C;H0;D3;+0:1](=O)-[C:2](-[F;D1;H0:3])(-[F;D1;H0:4])-[F;D1;H0:5].[C:6]-[#7;a:7]1:[c:8]2:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:2:[c:13](=[O;D1;H0:14]):[nH;D2;+0:15]/[c;H0;D3;+0:16]:1=[N;H0;D2;+0:17]\[NH2;D1;+0:18]>>[C:6]-[#7;a:7]1:[c:8]2:[#7;a:9]:[c:10]:[#7;a:11]:[c:12]:2:[c:13](=[O;D1;H0:14]):[n;H0;D3;+0:15]2:[c;H0;D3;+0:... | 60.2 | [{"value": 60.2, "product": "C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The mixture of (2E)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (200 mg, 0.85 mmol) in trifluoroacetic acid (10 mL) was refluxed overnight. The reaction mixture was concentrated and purified by preparative LCMS to yield the desired product (160 mg, 60.2%). LCMS calculated for C12H14F3N6O(M+H): 315.1; found 315... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Carboxylic acid | null | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | HO- | null | null | null | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)C(F)(F)F>>CCCCCn1c2nc[nH]c2c(=O)n2c(C(F)(F)F)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fe69eed9dcbb4952854932a6a57d0406 | CCCCCn1c2nc[nH]c2c(=O)n2c(C(F)(F)F)nnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(C(F)(F)F)nnc12 | C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)C(F)(F)F.BrN1C(CCC1=O)=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)C(F)(F)F)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([C:17]([F:18])([F:19])[F:20])[n:21][n:22][c:23]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([C:17]([F:18])([F:19])[F:20])[n:21][n:... | CCCCCn1c2nc[nH]c2c(=O)n2c(C(F)(F)F)nnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(C(F)(F)F)nnc12 | null | null | O1CCCC1 | Functional Group Interconversion | Bromination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nncn12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | null | [] | 70 | CELSIUS | 3 | HOUR | To the mixture of 9-pentyl-3-(trifluoromethyl)-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (50 mg, 0.16 mmol) in tetrahydrofuran (10 mL) was added N-bromosuccinimide (42 mg, 0.24 mmol). The mixture was stirred at 70° C. for 3 hour. The reaction mixture was concentrated and purified by preparative LCMS to yield the... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | HO- | O1CCCC1 | 70 | 3 | CCCCCn1c2nc[nH]c2c(=O)n2c(C(F)(F)F)nnc12.O=C1CCC(=O)N1Br>O1CCCC1>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(C(F)(F)F)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-38f8855b60e64eb4b4fb666f96d20f37 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21>>CCCCCn1c2nc[nH]c2c(=O)n2nnnc12 | N(=O)[O-].[Na+].C(CCCC)N1/C(/NC(C=2NC=NC12)=O)=N/N.C(=O)(O)[O-].[Na+]>>C(CCCC)N1C=2N(C(C=3NC=NC13)=O)N=NN2 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[nH:14]/[c:18]1=[N:17]\[NH2:16]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[n:15][n:16][n:17][c:18]12 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21 | CCCCCn1c2nc[nH]c2c(=O)n2nnnc12 | null | null | Cl | Aromatic Heterocycle Formation | OtherReaction | 4a2d3a022c4e462855afe5b24fdd580fb786023ed6771efe49fffa8dc9f9c8cf | d627647f8a5758e4c676083258d3a8813f47848ab7ceb334945a07e482fcef85 | O=c1c2[nH]cnc2[nH]c2nnnn12 | [C:1]-[#7;a:2]1:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8](=[O;D1;H0:9]):[nH;D2;+0:10]/[c;H0;D3;+0:11]:1=[N;H0;D2;+0:12]\[NH2;D1;+0:13]>>[C:1]-[#7;a:2]1:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8](=[O;D1;H0:9]):[n;H0;D3;+0:10]2:[#7;a:14]:[n;H0;D2;+0:13]:[n;H0;D2;+0:12]:[c;H0;D3;+0:11]:1:2 | 60.7 | [{"value": 60.7, "product": "C(CCCC)N1C=2N(C(C=3NC=NC13)=O)N=NN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.7, "product": "C(CCCC)N1C=2N(C(C=3NC=NC13)=O)N=NN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A saturated aqueous NaNO2 (130 mg, 1.89 mmol) solution was added dropwise to a solution of (2E)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (150 mg, 0.63 mmol) in 5% aqueous HCl solution (3 ml) under stirring at room temperature. The mixture was stirred at room temperature for 1 hour. The mixture was neutraliz... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone | null | c1ncc2nc[nH]c2n1 | c1nc2cn3nnnc3nc2[nH]1 | c1nc2cn3nnnc3nc2[nH]1 | Other | Cl | null | null | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21>Cl>CCCCCn1c2nc[nH]c2c(=O)n2nnnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-51d144eb104145759652ecd78e3a16f8 | CCCCCn1c2nc[nH]c2c(=O)n2nnnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2nnnc12 | C(CCCC)N1C=2N(C(C=3NC=NC13)=O)N=NN2.C1CC(=O)N(C1=O)Br>>BrC1=NC=2N(C=3N(C(C2N1)=O)N=NN3)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[n:16][n:17][n:18][c:19]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2[n:16][n:17][n:18][c:19]12 | CCCCCn1c2nc[nH]c2c(=O)n2nnnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2nnnc12 | null | null | C1CCOC1 | Functional Group Interconversion | Bromination | 9d56eb9229def6a6a2150d3c9b0d77729b7e3999fc1a49c972b658a33130521c | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nnnn12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[C:2]-[#7;a:3]1:[c:4]2:[#7;a:5]:[#7;a:6]:[#7;a:7]:[#7;a:8]:2:[c:9]:[c:10]2:[#7;a:11]:[cH;D2;+0:12]:[#7;a:13]:[c:14]:1:2>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:12]1:[#7;a:11]:[c:10]2:[c:9]:[#7;a:8]3:[#7;a:7]:[#7;a:6]:[#7;a:5]:[c:4]:3:[#7;a:3](-[C:2]):[c:14]:2:[#7;a:13]:1 | 13.8 | [{"value": 13.7, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)N=NN3)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 13.8, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)N=NN3)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 1 | HOUR | The mixture of 4-pentyl-4,7-dihydro-8H-tetrazolo[1,5-a]purin-8-one (94.6 mg, 0.38 mmol) and NBS (75 mg, 0.42 mmol) in THF (20 ml) was stirred at 70° C. for 1 hour. After evaporation of solvent, the residue was purified by preparative LC-MS to yield the desired product (17.1 mg, 13.7%). LCMS calculated for C10H13BrN7O(M... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3nnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3nnnc3nc2[nH]1 | c1nc2cn3nnnc3nc2[nH]1 | HO- | C1CCOC1 | 70 | 1 | CCCCCn1c2nc[nH]c2c(=O)n2nnnc12.O=C1CCC(=O)N1Br>C1CCOC1>CCCCCn1c2nc(Br)[nH]c2c(=O)n2nnnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a1a59a4f2aa94d2daed7eab7e7570ff3 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=CCCC(=O)O>>CCCCCn1/c(=N/N=C/CCC(=O)O)[nH]c(=O)c2[nH]cnc21 | C(CCCC)N1/C(/NC(C=2NC=NC12)=O)=N/N.O=CCCC(=O)O>>O=C1C=2NC=NC2N(\C(\N1)=N\N=C\CCC(=O)O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH2:9])[nH:16][c:17](=[O:18])[c:19]2[nH:20][cH:21][n:22][c:23]12.O=[CH:10][CH2:11][CH2:12][C:13](=[O:14])[OH:15]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[N:9]=[CH:10]/[CH2:11][CH2:12][C:13](=[O:14])[OH:15])[nH:16][c:17](=[O:18])[c:19]2[nH:20][cH:21... | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=CCCC(=O)O | CCCCCn1/c(=N/N=C/CCC(=O)O)[nH]c(=O)c2[nH]cnc21 | null | null | CCO | Heteroatom Alkylation and Arylation | OtherReaction | 369b3f62a39edf615315b2761263eb1b649612c7b3caef083e9b41e01b478de5 | a492f13607987389cdd7ab2f9f1199c71d7d1e56ec2df1828d06f8b8bbe23769 | N=c1[nH]c(=O)c2[nH]cnc2[nH]1 | O=[CH;D2;+0:1]-[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[O;D1;H1:6].[#7;a:7]/[c:8](=[#7:9]\[NH2;D1;+0:10]):[#7;a:11]>>[#7;a:7]/[c:8](=[#7:9]\[N;H0;D2;+0:10]=[CH;D2;+0:1]\[C:2]-[C:3]-[C:4](=[O;D1;H0:5])-[O;D1;H1:6]):[#7;a:11] | 96.6 | [{"value": 96.0, "product": "O=C1C=2NC=NC2N(\\C(\\N1)=N\\N=C\\CCC(=O)O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.6, "product": "O=C1C=2NC=NC2N(\\C(\\N1)=N\\N=C\\CCC(=O)O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The mixture of (2E)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (1.0 g, 4.2 mmol) and 4-oxobutanoic acid (3.4 g, 15% in water, 5.1 mmol) in EtOH (70 ml) was refluxed for 1.5 hours. Evaporation of solvent gave the desired product (1.3 g, 96%) as a yellowish solid. LCMS calculated for C14H21N6O3(M+H): 321.1; fou... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Aldehyde | null | null | null | c1ncc2[nH]cnc2n1 | HO- | CCO | null | null | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=CCCC(=O)O>CCO>CCCCCn1/c(=N/N=C/CCC(=O)O)[nH]c(=O)c2[nH]cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fcaa826f794e409285535240f57be409 | CCCCCn1/c(=N/N=C/CCC(=O)O)[nH]c(=O)c2[nH]cnc21>>CCCCCn1c2nc[nH]c2c(=O)n2c(CCC(=O)O)nnc12 | O=C1C=2NC=NC2N(\C(\N1)=N\N=C\CCC(=O)O)CCCCC>>O=C1C=2NC=NC2N(C=2N1C(=NN2)CCC(=O)O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[nH:14]/[c:23]1=[N:22]\[N:21]=[CH:15]\[CH2:16][CH2:17][C:18](=[O:19])[OH:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15]([CH2:16][CH2:17][C:18](=[O:19])[OH:20])[n:21][n:22][c:... | CCCCCn1/c(=N/N=C/CCC(=O)O)[nH]c(=O)c2[nH]cnc21 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCC(=O)O)nnc12 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 066077903128dcf5e3d8c17f71c894783195993eb8e78fea83753934f8800b97 | 42048ba06e684767e79a864f38d2ee087b4547e971032cda3c892dd210eef093 | O=c1c2[nH]cnc2[nH]c2nncn12 | [C:1]-[#7;a:2]1:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8](=[O;D1;H0:9]):[nH;D2;+0:10]/[c;H0;D3;+0:11]:1=[N;H0;D2;+0:12]\[N;H0;D2;+0:13]=[CH;D2;+0:14]\[C:15]-[C:16]-[C:17](=[O;D1;H0:18])-[O;D1;H1:19]>>[C:1]-[#7;a:2]1:[c:3]2:[#7;a:4]:[c:5]:[#7;a:6]:[c:7]:2:[c:8](=[O;D1;H0:9]):[n;H0;D3;+0:10]2:[c;H0;D3;+0:14](-[C:15]-[... | 99 | [{"value": 99.0, "product": "O=C1C=2NC=NC2N(C=2N1C(=NN2)CCC(=O)O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.5, "product": "O=C1C=2NC=NC2N(C=2N1C(=NN2)CCC(=O)O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The mixture of (4E)-4-[(2E)-(6-oxo-3-pentyl-1,3,6,7-tetrahydro-2H-purin-2-ylidene)hydrazono]butanoic acid (1.367 g, 5.1 mmol) in acetic acid (70 ml) was refluxed for 1 hour. Evaporation of solvent afforded the desired product (1.29 g, 99%) as yellowish solid. LCMS calculated for C14H19N6O3(M+H): 319.2; found: 319.2.
Co... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | null | C(C)(=O)O | null | null | CCCCCn1/c(=N/N=C/CCC(=O)O)[nH]c(=O)c2[nH]cnc21>C(C)(=O)O>CCCCCn1c2nc[nH]c2c(=O)n2c(CCC(=O)O)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f8bce98c4063463ba012f9dc6e29a4d9 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCC(=O)O)nnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCC(=O)O)nnc12 | O=C1C=2NC=NC2N(C=2N1C(=NN2)CCC(=O)O)CCCCC.C1CC(=O)N(C1=O)Br>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCC(=O)O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH2:17][CH2:18][C:19](=[O:20])[OH:21])[n:22][n:23][c:24]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH2:17][CH2:18][C:19](=[O:2... | CCCCCn1c2nc[nH]c2c(=O)n2c(CCC(=O)O)nnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCC(=O)O)nnc12 | null | null | C1CCOC1 | Functional Group Interconversion | Bromination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nncn12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | 23.7 | [{"value": 23.7, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCC(=O)O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 2 | HOUR | The mixture of 3-(5-oxo-9-pentyl-6,9-dihydro-5H[1,2,4]triazolo[4,3-a]purin-3-yl)propanoic acid (203 mg, 0.64 mmole) and NBS (125.8 mg, 7.0 mmol) in THF (25 ml) was stirred at 70° C. for 2 hours. After evaporation of solvent, the residue was purified by preparative LC-MS to afford 60.2 mg (23.7%) of the desired product ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | HO- | C1CCOC1 | 70 | 2 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCC(=O)O)nnc12.O=C1CCC(=O)N1Br>C1CCOC1>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCC(=O)O)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74cc70bfb85842a5b0ee3a6e77d0cdcc | C1COCCN1.CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCC(=O)O)nnc12>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCC(=O)N3CCOCC3)nnc12 | BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCC(=O)O)CCCCC.N1CCOCC1.C(C)N(CC)CC.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCC(=O)N3CCOCC3)CCCCC | [NH:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1.O[C:19]([CH2:18][CH2:17][c:16]1[n:15]2[c:13](=[O:14])[c:12]3[c:7]([n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:29]2[n:28][n:27]1)[n:8][c:9]([Br:10])[nH:11]3)=[O:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:1... | C1COCCN1.CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCC(=O)O)nnc12 | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCC(=O)N3CCOCC3)nnc12 | null | null | C(Cl)Cl | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | 2ef483949e7ba3e5f888cf14cdce25fa611f75be09fdf1854a473be519821b59 | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(CCc1nnc2[nH]c3nc[nH]c3c(=O)n12)N1CCOCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#8:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[#8:5]-[C:10]-[C:9]-1 | 63.3 | [{"value": 60.0, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCC(=O)N3CCOCC3)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 63.3, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCC(=O)N3CCOCC3)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | The mixture of 3-(7-bromo-5-oxo-9-pentyl-6,9-dihydro-5H[1,2,4]triazolo[4,3-a]purin-3-yl]propanoic acid (50 mg, 0.126 mmol), morpholine (21.0 mg, 0.252 mmol), triethylamine (25.5 mg, 0.252 mmol) and BOP (61.5 mg, 0.139 mmol) in CH2Cl2 (10 ml) was stirred at room temperature for 2 hours. After evaporation of solvent, the... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | C1COCCN1 | C1COCC[NH]1 | C1COCC[NH]1.c1nc2cn3cnnc3nc2[nH]1 | HO- | C(Cl)Cl | null | 2 | C1COCCN1.CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCC(=O)O)nnc12>C(Cl)Cl>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCC(=O)N3CCOCC3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d51dd7d15d5e4298aa7b7e63bbb7ea18 | N#CCc1ccc(C(F)(F)F)cc1.NO>>N/C(Cc1ccc(C(F)(F)F)cc1)=N\O | FC(C1=CC=C(C=C1)CC#N)(F)F.Cl.NO.C(=O)(O)[O-].[Na+]>>O\N=C(\CC1=CC=C(C=C1)C(F)(F)F)/N | [N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][cH:13]1.[NH2:14][OH:15]>>[NH2:1]/[C:2]([CH2:3][c:4]1[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][cH:13]1)=[N:14]\[OH:15] | N#CCc1ccc(C(F)(F)F)cc1.NO | N/C(Cc1ccc(C(F)(F)F)cc1)=N\O | null | null | CO | Heteroatom Alkylation and Arylation | Amidoxime from nitrile and hydroxylamine | 5f2123b5002b6939ec57e4f55921371a47c78c3ff253c724d87881638fedcd4f | ad3f1127a4d99506976df608684863fb1e08b35faede2d4e31cf4ca96393cd2e | c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[C:3]-[c:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[NH2;D1;+0:1]/[C;H0;D3;+0:2](-[C:3]-[c:4])=[N;H0;D2;+0:5]\[O;D1;H1:6] | 84.9 | [{"value": 84.9, "product": "O\\N=C(\\CC1=CC=C(C=C1)C(F)(F)F)/N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.9, "product": "O\\N=C(\\CC1=CC=C(C=C1)C(F)(F)F)/N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A suspension of [4-(trifluoromethyl)phenyl]acetonitrile (1.0 g, 5.4 mmoles), hydroxylamine hydrochloride (0.41 g, 5.9 mmoles) and NaHCO3 (0.50 g, 5.9 mmoles) in MeOH (15 ml) was refluxed for 4 hours. The reaction mixture was then concentrated to remove the solvent methanol. The residue was extracted with ethyl acetate.... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Primary amine.Oxime | null | null | c1ccccc1 | null | CO | null | null | N#CCc1ccc(C(F)(F)F)cc1.NO>CO>N/C(Cc1ccc(C(F)(F)F)cc1)=N\O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-589a443feaaf49d99d07b72436c20dee | COC(=O)CCC(=O)[O-].N/C(Cc1ccccc1)=N\O>>COC(=O)CCc1nc(Cc2ccccc2)no1 | C(CCC(=O)[O-])(=O)OC.C1=CN(C=N1)C(=O)N2C=CN=C2.O\N=C(\CC1=CC=CC=C1)/N>>C(C1=CC=CC=C1)C1=NOC(=N1)CCC(=O)OC | O=[C:7]([O-])[CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4].[NH2:8]/[C:9]([CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)=[N:17]\[OH:18]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[n:8][c:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:17][o:18]1 | COC(=O)CCC(=O)[O-].N/C(Cc1ccccc1)=N\O | COC(=O)CCc1nc(Cc2ccccc2)no1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | d5c6320841f1ab27aeecb31a475839e66def5aa9eb9bb79c83570ae0a04a0046 | e4d0a49bc358c8febd1a5e454066b0a955c97759f5381ecc96c210781772c661 | c1ccc(Cc2ncon2)cc1 | O=[C;H0;D3;+0:1](-[O-])-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[NH2;D1;+0:7]/[C;H0;D3;+0:8](-[C:9]-[c:10])=[N;H0;D2;+0:11]\[OH;D1;+0:12]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:7]:[c;H0;D3;+0:8](-[C:9]-[c:10]):[n;H0;D2;+0:11]:[o;H0;D2;+0:12]:1 | 69.7 | [{"value": 69.7, "product": "C(C1=CC=CC=C1)C1=NOC(=N1)CCC(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.7, "product": "C(C1=CC=CC=C1)C1=NOC(=N1)CCC(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Butanedioic acid, monomethyl ester (4.0 g, 30.3 mmole) and CDI (5.40 g, 33.3 mmole) were dissolved in anhydrous DMF (15 ml). After stirring the solution at room temperature for 3 hours, (1Z)-N′-hydroxy-2-phenylethanimidamide (5.0 g, 33.3 mmole) was added and the solution heated at 90° C. for 20 hours. After evaporation... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Oxime | null | null | c1ncon1 | c1ncon1.c1ccccc1 | HO- | CN(C)C=O | null | 3 | COC(=O)CCC(=O)[O-].N/C(Cc1ccccc1)=N\O>CN(C)C=O>COC(=O)CCc1nc(Cc2ccccc2)no1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-aa85ff1308584931b01fcd4382dc7026 | COC(=O)CCc1nc(Cc2ccccc2)no1>>O=C(O)CCc1nc(Cc2ccccc2)no1 | C(C1=CC=CC=C1)C1=NOC(=N1)CCC(=O)OC.[OH-].[Na+]>>C(C1=CC=CC=C1)C1=NOC(=N1)CCC(=O)O | C[O:3][C:2](=[O:1])[CH2:4][CH2:5][c:6]1[n:7][c:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][o:17]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][c:6]1[n:7][c:8]([CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][o:17]1 | COC(=O)CCc1nc(Cc2ccccc2)no1 | O=C(O)CCc1nc(Cc2ccccc2)no1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(Cc2ncon2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 98 | [{"value": 98.0, "product": "C(C1=CC=CC=C1)C1=NOC(=N1)CCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.0, "product": "C(C1=CC=CC=C1)C1=NOC(=N1)CCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of methyl 3-(3-benzyl-1,2,4-oxadiazol-5-yl)propanoate (5.2 g, 21.1 mmole) in methanol (30 ml) was added 50 ml of 1N NaOH. The mixture was stirred at room temperature for 2 hours. The mixture was adjusted to PH=3-4 under ice bath, and extracted with EtOAc (3×). The combined organic phases were washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ncon1.c1ccccc1 | Other | CO | null | 2 | COC(=O)CCc1nc(Cc2ccccc2)no1>CO>O=C(O)CCc1nc(Cc2ccccc2)no1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-821af4ae7034437e9f13426e6590559d | CCCCCn1/c(=N/NC(=O)CCc2nc(Cc3ccccc3)no2)[nH]c(=O)c2[nH]c(C(F)(F)F)nc21>>CCCCCn1c2nc(C(F)(F)F)[nH]c2c(=O)n2c(CCc3nc(Cc4ccccc4)no3)nnc12 | C(C1=CC=CC=C1)C1=NOC(=N1)CCC(=O)N/N=C/1\NC(C=2NC(=NC2N1CCCCC)C(F)(F)F)=O>>C(C1=CC=CC=C1)C1=NOC(=N1)CCC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)C(F)(F)F)=O | O=[C:19]([CH2:20][CH2:21][c:22]1[n:23][c:24]([CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[n:32][o:33]1)[NH:34]/[N:35]=[c:36]1/[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:7]2[n:8][c:9]([C:10]([F:11])([F:12])[F:13])[nH:14][c:15]2[c:16](=[O:17])[nH:18]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([... | CCCCCn1/c(=N/NC(=O)CCc2nc(Cc3ccccc3)no2)[nH]c(=O)c2[nH]c(C(F)(F)F)nc21 | CCCCCn1c2nc(C(F)(F)F)[nH]c2c(=O)n2c(CCc3nc(Cc4ccccc4)no3)nnc12 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | f919762557f16e8feb47c1fb62f203cd1ec4ed5f009cf276d2d0e0ec84ef6b80 | 78b0616e5760c6d4dadfc1fac5c58c0254d0dc7b1bf102fea4bc1349928b0776 | O=c1c2[nH]cnc2[nH]c2nnc(CCc3nc(Cc4ccccc4)no3)n12 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[NH;D2;+0:4]/[N;H0;D2;+0:5]=[c;H0;D3;+0:6]1\[nH;D2;+0:7]:[c:8](=[O;D1;H0:9]):[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:2:[#7;a:15]:1-[C:16]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:5]:[c;H0;D3;+0:6]2:[#7;a:15](-[C:16]):[c:14]3:[#7;a:13]:[c:12]:[#7;a:11]:[c:10]:3:[c:8](=[O;D... | 17.9 | [{"value": 17.8, "product": "C(C1=CC=CC=C1)C1=NOC(=N1)CCC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 17.9, "product": "C(C1=CC=CC=C1)C1=NOC(=N1)CCC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)C(F)(F)F)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The mixture of 3-(3-benzyl-1,2,4-oxadiazol-5-yl)-N′-[(2E)-6-oxo-3-pentyl-8-(trifluoromethyl)-1,3,6,7-tetrahydro-2H-purin-2-ylidene]propanohydrazide (220.1 mg, 0.424 mmole) in toluene (20 ml) was refluxed for 5 hours. After evaporation of solvent, the residue was purified by preparative LCMS to yield the desired product... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide | null | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | c1ncon1.c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | C1(=CC=CC=C1)C | null | null | CCCCCn1/c(=N/NC(=O)CCc2nc(Cc3ccccc3)no2)[nH]c(=O)c2[nH]c(C(F)(F)F)nc21>C1(=CC=CC=C1)C>CCCCCn1c2nc(C(F)(F)F)[nH]c2c(=O)n2c(CCc3nc(Cc4ccccc4)no3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3805461a52d641f885f11aa035677179 | COC(=O)CCC(=O)[O-].NNC(=O)c1ccccc1>>COC(=O)CCC(=O)NNC(=O)c1ccccc1 | C(C1=CC=CC=C1)(=O)NN.C(CCC(=O)[O-])(=O)OC.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C)(C)N(C(C)C)CC>>C(C1=CC=CC=C1)(=O)NNC(CCC(=O)OC)=O | [O-][C:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[O:8].[NH2:9][NH:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][C:7](=[O:8])[NH:9][NH:10][C:11](=[O:12])[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | COC(=O)CCC(=O)[O-].NNC(=O)c1ccccc1 | COC(=O)CCC(=O)NNC(=O)c1ccccc1 | null | CN(C1=CC=NC=C1)C | CN(C)C=O | Acylation | OtherReaction | 84d993f2dd8c5d113c44b49ecd8621492b66c5d2b94f73a7d5ff99800e371df5 | b956b8a4acbeafca0fa5a0ba87177355a422ec6427e7d47cc2545547616c0ab5 | c1ccccc1 | [#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[C;H0;D3;+0:6](-[O-])=[O;D1;H0:7].[NH2;D1;+0:8]-[#7:9]-[C:10](=[O;D1;H0:11])-[c:12]>>[#8:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5]-[C;H0;D3;+0:6](=[O;D1;H0:7])-[NH;D2;+0:8]-[#7:9]-[C:10](=[O;D1;H0:11])-[c:12] | 32.7 | [{"value": 32.6, "product": "C(C1=CC=CC=C1)(=O)NNC(CCC(=O)OC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 32.7, "product": "C(C1=CC=CC=C1)(=O)NNC(CCC(=O)OC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | The mixture of benzhydrazide (1.5 g, 11.0 mmol), butanedioic acid, monomethyl ester (2.0 g, 15 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (5.4 g, 12 mmol), N,N-diisopropylethylamine (3.8 mL, 22 mmol) and 4-dimethylaminopyridine (0.87 g, 7.2 mmol) in DMF (30 mL) was stirred at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine | Acylhydrazine.Acylhydrazine | null | null | c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.CN(C)C=O | null | 8 | COC(=O)CCC(=O)[O-].NNC(=O)c1ccccc1>CN(C1=CC=NC=C1)C.CN(C)C=O>COC(=O)CCC(=O)NNC(=O)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-76b0c845b0fb4a93891c0a3157acf0dd | COC(=O)CCC(=O)NNC(=O)c1ccccc1>>COC(=O)CCc1nnc(-c2ccccc2)o1 | S(=O)(Cl)Cl.C(C1=CC=CC=C1)(=O)NNC(CCC(=O)OC)=O.N1=CC=CC=C1>>C1(=CC=CC=C1)C1=NN=C(O1)CCC(=O)OC | O=[C:7]([CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[NH:8][NH:9][C:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)=[O:17]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][c:7]1[n:8][n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[o:17]1 | COC(=O)CCC(=O)NNC(=O)c1ccccc1 | COC(=O)CCc1nnc(-c2ccccc2)o1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | ef130645674b014a808ae327ff67ae63a4b0fba1781fc176f61089abd6ffd017 | b3d4fa0dcfa02ac7642075a89f830594ba71dc7452e661900a986719bd6ddb0a | c1ccc(-c2nnco2)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6])-[NH;D2;+0:7]-[NH;D2;+0:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:7]:[n;H0;D2;+0:8]:[c;H0;D3;+0:9](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]):[o;H0;D2... | 72 | [{"value": 72.0, "product": "C1(=CC=CC=C1)C1=NN=C(O1)CCC(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.6, "product": "C1(=CC=CC=C1)C1=NN=C(O1)CCC(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Thionyl chloride (0.34 mL, 4.7 mmol) was added to the mixture of methyl 4-(2-benzoylhydrazino)-4-oxobutanoate (900 mg, 4 mmol), Pyridine (0.87 mL, 0.011 mol) in tetrahydrofuran (20 mL) at room temperature. After stirring for 3 hours, the reaction mixture was concentrated. The residue was mixed with toluene (20 mL) and ... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Acylhydrazine | null | null | c1nnco1 | c1nnco1.c1ccccc1 | HO- | O1CCCC1 | null | 3 | COC(=O)CCC(=O)NNC(=O)c1ccccc1>O1CCCC1>COC(=O)CCc1nnc(-c2ccccc2)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7346673dc2d34e998c69654afd855478 | COC(=O)CCc1nnc(-c2ccccc2)o1>>O=C(O)CCc1nnc(-c2ccccc2)o1 | C1(=CC=CC=C1)C1=NN=C(O1)CCC(=O)OC>>C1(=CC=CC=C1)C1=NN=C(O1)CCC(=O)O | C[O:3][C:2](=[O:1])[CH2:4][CH2:5][c:6]1[n:7][n:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[o:16]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][c:6]1[n:7][n:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[o:16]1 | COC(=O)CCc1nnc(-c2ccccc2)o1 | O=C(O)CCc1nnc(-c2ccccc2)o1 | null | null | CO.[OH-].[Na+] | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2nnco2)cc1 | C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 114.6 | [{"value": 83.0, "product": "C1(=CC=CC=C1)C1=NN=C(O1)CCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 114.6, "product": "C1(=CC=CC=C1)C1=NN=C(O1)CCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of methyl 3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanoate (600 mg, 2.0 mmol) in 1 M of aqueous NaOH (10 mL) and Methanol (10 mL) was stirred at room temperature overnight. The reaction solution was adjusted to pH 5 and extracted with ethyl acetate three times. The combined organic layers were dried, filtered and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1nnco1.c1ccccc1 | Other | CO.[OH-].[Na+] | null | 8 | COC(=O)CCc1nnc(-c2ccccc2)o1>CO.[OH-].[Na+]>O=C(O)CCc1nnc(-c2ccccc2)o1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0f318cc8935a474185eba9878b8756d9 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)CCc1nnc(-c2ccccc2)o1>>CCCCCn1/c(=N/NC(=O)CCc2nnc(-c3ccccc3)o2)[nH]c(=O)c2[nH]cnc21 | C1(=CC=CC=C1)C1=NN=C(O1)CCC(=O)O.C(CCCC)N1/C(/NC(C=2NC=NC12)=O)=N/N.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C)(C)N(C(C)C)CC>>O=C1C=2NC=NC2N(\C(\N1)=N\NC(CCC=1OC(=NN1)C1=CC=CC=C1)=O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH2:9])[nH:25][c:26](=[O:27])[c:28]2[nH:29][cH:30][n:31][c:32]12.O[C:10](=[O:11])[CH2:12][CH2:13][c:14]1[n:15][n:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[o:24]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH:9][C:10](=[O:11])[CH2:12][CH... | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)CCc1nnc(-c2ccccc2)o1 | CCCCCn1/c(=N/NC(=O)CCc2nnc(-c3ccccc3)o2)[nH]c(=O)c2[nH]cnc21 | null | CN(C1=CC=NC=C1)C | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | e50d935ef072f0718d4e131af3df793f26e2f0a63884801973739584ab6e55ba | 2740512737e2508c1c8d407d0ee271fd1e1c46ad16223e8e2fc1e12936af0dea | O=C(CCc1nnc(-c2ccccc2)o1)N/N=c1\[nH]c(=O)c2[nH]cnc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]/[c:6](=[#7:7]\[NH2;D1;+0:8]):[#7;a:9]>>[#7;a:5]/[c:6](=[#7:7]\[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]):[#7;a:9] | 55.6 | [{"value": 48.5, "product": "O=C1C=2NC=NC2N(\\C(\\N1)=N\\NC(CCC=1OC(=NN1)C1=CC=CC=C1)=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.6, "product": "O=C1C=2NC=NC2N(\\C(\\N1)=N\\NC(CCC=1OC(=NN1)C1=CC=CC=C1)=O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | The mixture of 3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanoic acid (500 mg, 20 mmol), (2E)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (480 mg, 0.0020 mol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (980 mg, 22 mmol), 4-dimethylaminopyridine (100 mg, 10 mmol), and N,N-diisopropylethyla... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Carboxylic acid | Hydrazone amide | null | null | c1nnco1.c1ccccc1.c1ncc2[nH]cnc2n1 | HO- | CN(C1=CC=NC=C1)C.CN(C)C=O | null | 8 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)CCc1nnc(-c2ccccc2)o1>CN(C1=CC=NC=C1)C.CN(C)C=O>CCCCCn1/c(=N/NC(=O)CCc2nnc(-c3ccccc3)o2)[nH]c(=O)c2[nH]cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b4ec69433a0646868f0ce761d1b9dbae | CCCCCn1/c(=N/NC(=O)CCc2nnc(-c3ccccc3)o2)[nH]c(=O)c2[nH]cnc21>>CCCCCn1c2nc[nH]c2c(=O)n2c(CCc3nnc(-c4ccccc4)o3)nnc12 | O=C1C=2NC=NC2N(\C(\N1)=N\NC(CCC=1OC(=NN1)C1=CC=CC=C1)=O)CCCCC>>C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)CCC=2OC(=NN2)C2=CC=CC=C2 | O=[C:15]([CH2:16][CH2:17][c:18]1[n:19][n:20][c:21](-[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[o:28]1)[NH:29]/[N:30]=[c:31]1/[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[nH:14]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[... | CCCCCn1/c(=N/NC(=O)CCc2nnc(-c3ccccc3)o2)[nH]c(=O)c2[nH]cnc21 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCc3nnc(-c4ccccc4)o3)nnc12 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | f919762557f16e8feb47c1fb62f203cd1ec4ed5f009cf276d2d0e0ec84ef6b80 | 78b0616e5760c6d4dadfc1fac5c58c0254d0dc7b1bf102fea4bc1349928b0776 | O=c1c2[nH]cnc2[nH]c2nnc(CCc3nnc(-c4ccccc4)o3)n12 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[NH;D2;+0:4]/[N;H0;D2;+0:5]=[c;H0;D3;+0:6]1\[nH;D2;+0:7]:[c:8](=[O;D1;H0:9]):[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:2:[#7;a:15]:1-[C:16]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:5]:[c;H0;D3;+0:6]2:[#7;a:15](-[C:16]):[c:14]3:[#7;a:13]:[c:12]:[#7;a:11]:[c:10]:3:[c:8](=[O;D... | 66.7 | [{"value": 66.7, "product": "C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)CCC=2OC(=NN2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.7, "product": "C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)CCC=2OC(=NN2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The mixture of N′-[(2E)-6-oxo-3-pentyl-1,3,6,7-tetrahydro-2H-purin-2-ylidene]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)propanohydrazide (485 mg, 1.11 mmol) in toluene (50 mL) was heated to reflux overnight. The mixture was concentrated to yield the desired product (310 mg, 66.7%). LCMS calculated for C21H23N8O2(M+H): 419.2; fo... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide | null | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | c1nnco1.c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | C1(=CC=CC=C1)C | null | null | CCCCCn1/c(=N/NC(=O)CCc2nnc(-c3ccccc3)o2)[nH]c(=O)c2[nH]cnc21>C1(=CC=CC=C1)C>CCCCCn1c2nc[nH]c2c(=O)n2c(CCc3nnc(-c4ccccc4)o3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5acbf9d09b654b9cb793f0534470d859 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCc3nnc(-c4ccccc4)o3)nnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCc3nnc(-c4ccccc4)o3)nnc12 | C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)CCC=2OC(=NN2)C2=CC=CC=C2.BrN1C(CCC1=O)=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCC=3OC(=NN3)C3=CC=CC=C3)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH2:17][CH2:18][c:19]3[n:20][n:21][c:22](-[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[o:29]3)[n:30][n:31][c:32]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[... | CCCCCn1c2nc[nH]c2c(=O)n2c(CCc3nnc(-c4ccccc4)o3)nnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCc3nnc(-c4ccccc4)o3)nnc12 | null | null | C1CCOC1 | Functional Group Interconversion | Bromination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nnc(CCc3nnc(-c4ccccc4)o3)n12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | null | [] | 70 | CELSIUS | 1 | HOUR | The mixture of 9-pentyl-3-[2-(5-phenyl-1,3,4-oxadiazol-2-yl)ethyl]-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (53 mg, 0.13 mmol) and N-bromosuccinimide (34 mg, 0.19 mmol) in THF (20 mL) was stirred at 70° C. for 1 hour. The reaction mixture was concentrated and the residue was purified by preparative LCMS to give... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1nnco1.c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | C1CCOC1 | 70 | 1 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCc3nnc(-c4ccccc4)o3)nnc12.O=C1CCC(=O)N1Br>C1CCOC1>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCc3nnc(-c4ccccc4)o3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-55f0a84af50345f786b2d2064854d6f1 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)CNC(=O)OCc1ccccc1>>CCCCCn1/c(=N/NC(=O)CNC(=O)OCc2ccccc2)[nH]c(=O)c2[nH]cnc21 | C(CCCC)N1/C(/NC(C=2NC=NC12)=O)=N/N.C(=O)(OCC1=CC=CC=C1)NCC(=O)O.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C)N(CC)CC>>O=C(CNC(OCC1=CC=CC=C1)=O)N/N=C/1\NC(C=2NC=NC2N1CCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH2:9])[nH:24][c:25](=[O:26])[c:27]2[nH:28][cH:29][n:30][c:31]12.O[C:10](=[O:11])[CH2:12][NH:13][C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH:9][C:10](=[O:11])[CH2:12][NH:13][C:... | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)CNC(=O)OCc1ccccc1 | CCCCCn1/c(=N/NC(=O)CNC(=O)OCc2ccccc2)[nH]c(=O)c2[nH]cnc21 | null | null | CN(C)C=O.CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | e50d935ef072f0718d4e131af3df793f26e2f0a63884801973739584ab6e55ba | 2740512737e2508c1c8d407d0ee271fd1e1c46ad16223e8e2fc1e12936af0dea | O=C(CNC(=O)OCc1ccccc1)N/N=c1\[nH]c(=O)c2[nH]cnc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6].[#7;a:7]/[c:8](=[#7:9]\[NH2;D1;+0:10]):[#7;a:11]>>[#7;a:7]/[c:8](=[#7:9]\[NH;D2;+0:10]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4]-[C:5]=[O;D1;H0:6]):[#7;a:11] | 144.8 | [{"value": 86.0, "product": "O=C(CNC(OCC1=CC=CC=C1)=O)N/N=C/1\\NC(C=2NC=NC2N1CCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 144.8, "product": "O=C(CNC(OCC1=CC=CC=C1)=O)N/N=C/1\\NC(C=2NC=NC2N1CCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | The mixture of (2E)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (0.50 g, 0.0021 mol), N-carbobenzyloxyglycine (0.49 g, 0.0023 mol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.0 g, 2.3 mmol) and triethylamine (0.59 mL, 0.0042 mol) in DMF (20 mL) was stirred at room temperature ove... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Carboxylic acid | Hydrazone amide | null | null | c1ccccc1.c1ncc2[nH]cnc2n1 | HO- | CN(C)C=O.CCOC(=O)C | null | 8 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)CNC(=O)OCc1ccccc1>CN(C)C=O.CCOC(=O)C>CCCCCn1/c(=N/NC(=O)CNC(=O)OCc2ccccc2)[nH]c(=O)c2[nH]cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2773aaf43dfa4286919f9a00d95706a5 | CCCCCn1/c(=N/NC(=O)CNC(=O)OCc2ccccc2)[nH]c(=O)c2[nH]cnc21>>CCCCCn1c2nc[nH]c2c(=O)n2c(CNC(=O)OCc3ccccc3)nnc12 | O=C(CNC(OCC1=CC=CC=C1)=O)N/N=C/1\NC(C=2NC=NC2N1CCCCC)=O>>O=C1C=2NC=NC2N(C=2N1C(=NN2)CNC(OCC2=CC=CC=C2)=O)CCCCC | O=[C:15]([CH2:16][NH:17][C:18](=[O:19])[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[NH:28]/[N:29]=[c:30]1/[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[nH:14]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15]([... | CCCCCn1/c(=N/NC(=O)CNC(=O)OCc2ccccc2)[nH]c(=O)c2[nH]cnc21 | CCCCCn1c2nc[nH]c2c(=O)n2c(CNC(=O)OCc3ccccc3)nnc12 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | f919762557f16e8feb47c1fb62f203cd1ec4ed5f009cf276d2d0e0ec84ef6b80 | 78b0616e5760c6d4dadfc1fac5c58c0254d0dc7b1bf102fea4bc1349928b0776 | O=C(NCc1nnc2[nH]c3nc[nH]c3c(=O)n12)OCc1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[#7:3]-[C:4]=[O;D1;H0:5])-[NH;D2;+0:6]/[N;H0;D2;+0:7]=[c;H0;D3;+0:8]1\[nH;D2;+0:9]:[c:10](=[O;D1;H0:11]):[c:12]2:[#7;a:13]:[c:14]:[#7;a:15]:[c:16]:2:[#7;a:17]:1-[C:18]>>[C:18]-[#7;a:17]1:[c:16]2:[#7;a:15]:[c:14]:[#7;a:13]:[c:12]:2:[c:10](=[O;D1;H0:11]):[n;H0;D3;+0:9]2:[c;H0;D3;+0:1](-[C:2]-[#7:3... | 87.2 | [{"value": 87.0, "product": "O=C1C=2NC=NC2N(C=2N1C(=NN2)CNC(OCC2=CC=CC=C2)=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.2, "product": "O=C1C=2NC=NC2N(C=2N1C(=NN2)CNC(OCC2=CC=CC=C2)=O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The solution of benzyl 2-oxo-2-[(2E)-2-(6-oxo-3-pentyl-1,3,6,7-tetrahydro-2H-purin-2-ylidene)hydrazino]ethylcarbamate (0.60 g, 0.84 mmol) in toluene (30 mL) was refluxed overnight. M+H=410.1. The product was precipitated from the reaction mixture and filtered to give the desired product (300 mg, 87%). LCMS calculated f... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide | null | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | C1(=CC=CC=C1)C | null | null | CCCCCn1/c(=N/NC(=O)CNC(=O)OCc2ccccc2)[nH]c(=O)c2[nH]cnc21>C1(=CC=CC=C1)C>CCCCCn1c2nc[nH]c2c(=O)n2c(CNC(=O)OCc3ccccc3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-509439a3ab9a4aa4a6828bf58a381a1e | CCCCCn1c2nc[nH]c2c(=O)n2c(CNC(=O)OCc3ccccc3)nnc12>>CCCCCn1c2nc[nH]c2c(=O)n2c(CN)nnc12 | O=C1C=2NC=NC2N(C=2N1C(=NN2)CNC(OCC2=CC=CC=C2)=O)CCCCC.Cl>>Cl.NCC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O | O=C(OCc1ccccc1)[NH:17][CH2:16][c:15]1[n:14]2[c:12](=[O:13])[c:11]3[c:7]([n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:20]2[n:19][n:18]1)[n:8][cH:9][nH:10]3>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15]([CH2:16][NH2:17])[n:18][n:19][c:20]12 | CCCCCn1c2nc[nH]c2c(=O)n2c(CNC(=O)OCc3ccccc3)nnc12 | CCCCCn1c2nc[nH]c2c(=O)n2c(CN)nnc12 | null | [Pd] | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=c1c2[nH]cnc2[nH]c2nncn12 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2]-[c:3](:[#7;a:4]):[#7;a:5]:[#7;a:6]>>[#7;a:4]:[c:3](-[C:2]-[NH2;D1;+0:1]):[#7;a:5]:[#7;a:6] | 92 | [{"value": 92.0, "product": "Cl.NCC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To the solution of benzyl [(5-oxo-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-3-yl)methyl]carbamate (0.30 g, 0.73 mmol) in methanol (20 mL) and 1 mL of conc. HCl was added 110% Pd/C under N2. The mixture was shaken under 30 PSI H2 for 3 hours. The reaction mixture was filtered through celite and concentrated to... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1nc2cn3cnnc3nc2[nH]1 | HO- | [Pd].CO | null | 3 | CCCCCn1c2nc[nH]c2c(=O)n2c(CNC(=O)OCc3ccccc3)nnc12>[Pd].CO>CCCCCn1c2nc[nH]c2c(=O)n2c(CN)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-88222f041af54668a0322272cf79d9b1 | CCCCCn1c2nc[nH]c2c(=O)n2c(CN)nnc12.O=C(O)c1ccccc1>>CCCCCn1c2nc[nH]c2c(=O)n2c(CNC(=O)c3ccccc3)nnc12 | Cl.NCC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O.C(C1=CC=CC=C1)(=O)O.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C)N(CC)CC>>O=C1C=2NC=NC2N(C=2N1C(=NN2)CNC(C2=CC=CC=C2)=O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15]([CH2:16][NH2:17])[n:26][n:27][c:28]12.O[C:18](=[O:19])[c:20]1[cH:21][cH:22][cH:23][cH:24][cH:25]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15]([CH2:16][NH:17][C:1... | CCCCCn1c2nc[nH]c2c(=O)n2c(CN)nnc12.O=C(O)c1ccccc1 | CCCCCn1c2nc[nH]c2c(=O)n2c(CNC(=O)c3ccccc3)nnc12 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCc1nnc2[nH]c3nc[nH]c3c(=O)n12)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#7;a:6]:[c:7](-[C:8]-[NH2;D1;+0:9]):[#7;a:10]:[#7;a:11]>>[#7;a:6]:[c:7](-[C:8]-[NH;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[#7;a:10]:[#7;a:11] | 77.5 | [{"value": 77.0, "product": "O=C1C=2NC=NC2N(C=2N1C(=NN2)CNC(C2=CC=CC=C2)=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.5, "product": "O=C1C=2NC=NC2N(C=2N1C(=NN2)CNC(C2=CC=CC=C2)=O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | The mixture of 3-(aminomethyl)-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one hydrochloride (160 mg, 0.51 mmol), [B] benzoic Acid (0.069 g, 0.56 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.25 g, 0.56 mmol) and triethylamine (0.21 mL, 1.5 mmol) in DMF (10 mL) was stirred a... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | CN(C)C=O | null | 8 | CCCCCn1c2nc[nH]c2c(=O)n2c(CN)nnc12.O=C(O)c1ccccc1>CN(C)C=O>CCCCCn1c2nc[nH]c2c(=O)n2c(CNC(=O)c3ccccc3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b8a4e123163446e8907c9d8ce735263f | CCCCCn1c2nc[nH]c2c(=O)n2c(CNC(=O)c3ccccc3)nnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CNC(=O)c3ccccc3)nnc12 | O=C1C=2NC=NC2N(C=2N1C(=NN2)CNC(C2=CC=CC=C2)=O)CCCCC.BrN1C(CCC1=O)=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CNC(C3=CC=CC=C3)=O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH2:17][NH:18][C:19](=[O:20])[c:21]3[cH:22][cH:23][cH:24][cH:25][cH:26]3)[n:27][n:28][c:29]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2... | CCCCCn1c2nc[nH]c2c(=O)n2c(CNC(=O)c3ccccc3)nnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CNC(=O)c3ccccc3)nnc12 | null | null | C1CCOC1 | Functional Group Interconversion | Bromination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=C(NCc1nnc2[nH]c3nc[nH]c3c(=O)n12)c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | null | [] | 70 | CELSIUS | 1 | HOUR | To the solution of N-[(5-oxo-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-3-yl)methyl]benzamide (0.11 g, 0.28 mmol) in THF (10 mL) was added N-Bromosuccinimide (0.076 g, 0.42 mmol). The mixture was stirred at 70° C. for 1 hour. The reaction mixture was concentrated and purified by preparative LCMS. LCMS calculat... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | C1CCOC1 | 70 | 1 | CCCCCn1c2nc[nH]c2c(=O)n2c(CNC(=O)c3ccccc3)nnc12.O=C1CCC(=O)N1Br>C1CCOC1>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CNC(=O)c3ccccc3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-87c293b71b634136b711cbd10d1cee34 | CCCCCn1c(=S)[nH]c(=O)c2[nH]cnc21.COS(=O)(=O)OC>>CCCCCn1c(SC)nc(=O)c2[nH]cnc21 | C(CCCC)N1C(NC(C=2NC=NC12)=O)=S.S(=O)(=O)(OC)OC.C(C)(=O)O>>CSC1=NC(C=2NC=NC2N1CCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[S:8])[nH:10][c:11](=[O:12])[c:13]2[nH:14][cH:15][n:16][c:17]12.COS(=O)(=O)O[CH3:9]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]([S:8][CH3:9])[n:10][c:11](=[O:12])[c:13]2[nH:14][cH:15][n:16][c:17]12 | CCCCCn1c(=S)[nH]c(=O)c2[nH]cnc21.COS(=O)(=O)OC | CCCCCn1c(SC)nc(=O)c2[nH]cnc21 | null | null | O.[OH-].[Na+] | Heteroatom Alkylation and Arylation | OtherReaction | 0161fed9f1388ec369b7cbafe281cc52a2e7ee362447238b9354e3768807eefa | e73b6e23c9de2770653dfe1c031448ae08eae1a1e8b31e289bfc4b4719e52064 | O=c1nc[nH]c2nc[nH]c12 | C-O-S(=O)(=O)-O-[CH3;D1;+0:1].[C:2]-[#7;a:3]1:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:2:[c:9](=[O;D1;H0:10]):[nH;D2;+0:11]:[c;H0;D3;+0:12]:1=[S;H0;D1;+0:13]>>[C:2]-[#7;a:3]1:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:2:[c:9](=[O;D1;H0:10]):[n;H0;D2;+0:11]:[c;H0;D3;+0:12]:1-[S;H0;D2;+0:13]-[CH3;D1;+0:1] | 40 | [{"value": 40.0, "product": "CSC1=NC(C=2NC=NC2N1CCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.9, "product": "CSC1=NC(C=2NC=NC2N1CCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 3-pentyl-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one (13.0 g, 54.6 mmol) in 2 M of sodium hydroxide in water (250 mL) was added dimethyl sulfate (6.2 mL, 66 mmol), and the reaction mixture was stirred at room temperature for 1 hour, then neutralized with acetic acid. The precipitate was collected by fil... | 10.6084/m9.figshare.5104873.v1 | null | Thiocarbonyl | Monosulfide | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | HO- | O.[OH-].[Na+] | null | 1 | CCCCCn1c(=S)[nH]c(=O)c2[nH]cnc21.COS(=O)(=O)OC>O.[OH-].[Na+]>CCCCCn1c(SC)nc(=O)c2[nH]cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-58cc3e97c2ca4db5a597f0230a3f3407 | CCCCCn1c(SC)nc(=O)c2[nH]cnc21.N>>CCCCCn1c(N)nc(=O)c2[nH]cnc21 | CSC1=NC(C=2NC=NC2N1CCCCC)=O.[OH-].N>>NC1=NC(C=2NC=NC2N1CCCCC)=O | CS[c:7]1[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:16]2[c:12]([c:10](=[O:11])[n:9]1)[nH:13][cH:14][n:15]2.[NH3:8]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]([NH2:8])[n:9][c:10](=[O:11])[c:12]2[nH:13][cH:14][n:15][c:16]12 | CCCCCn1c(SC)nc(=O)c2[nH]cnc21.N | CCCCCn1c(N)nc(=O)c2[nH]cnc21 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f500e8e89d97d64d15e1420f37f84c3739bb246c9e00620675f4ee3b3fc90072 | fe235a2b93109096a39cf211c5494ce5db3b96d4e6b4b4ac937f939eb8bec4c8 | O=c1nc[nH]c2nc[nH]c12 | C-S-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4](:[#7;a:5]):[c:6](:[#7;a:7]):[#7;a:8]:1-[C:9].[NH3;D0;+0:10]>>[#7;a:5]:[c:4]1:[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH2;D1;+0:10]):[#7;a:8](-[C:9]):[c:6]:1:[#7;a:7] | 68 | [{"value": 68.0, "product": "NC1=NC(C=2NC=NC2N1CCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 4 | DAY | 2-(Methylthio)-3-pentyl-3,7-dihydro-6H-purin-6-one (5.0 g, 0.020 mol) was mixed with 100 ml of 28% ammonia hydroxide in a seal tube. The mixture was stirred at 100° C. for 4 days. After cooling to room temperature, the solid was filtered and dried to yield the desired product (3.0 g, 68%). LCMS calculated for C10H16N5O... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Primary amine | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | Other | null | 100 | 96 | CCCCCn1c(SC)nc(=O)c2[nH]cnc21.N>>CCCCCn1c(N)nc(=O)c2[nH]cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7b254ddca196496dbc382f1be0f01e0c | CCCCCn1c(=N)[nH]c(=O)c2[nH]cnc21.NN>>CCCCCn1c(=N)n(N)c(=O)c2[nH]cnc21 | N=C1NC(C=2NC=NC2N1CCCCC)=O.NN>>NN1C(N(C=2N=CNC2C1=O)CCCCC)=N | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[NH:8])[nH:9][c:11](=[O:12])[c:13]2[nH:14][cH:15][n:16][c:17]12.N[NH2:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7](=[NH:8])[n:9]([NH2:10])[c:11](=[O:12])[c:13]2[nH:14][cH:15][n:16][c:17]12 | CCCCCn1c(=N)[nH]c(=O)c2[nH]cnc21.NN | CCCCCn1c(=N)n(N)c(=O)c2[nH]cnc21 | null | null | O | Miscellaneous | OtherReaction | 0f4a18c44e3db037bff63652b6a4d971a509f3c51b7e12e9057738e30dfedc4d | ae87b85154e4ed9f19e174b708d1b263c1808f04035e196936e83905c9eea0fd | N=c1[nH]c(=O)c2[nH]cnc2[nH]1 | N-[NH2;D1;+0:1].[C:2]-[#7;a:3]1:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:2:[c:9](=[O;D1;H0:10]):[nH;D2;+0:11]:[c:12]:1=[N;D1;H1:13]>>[C:2]-[#7;a:3]1:[c:4]2:[#7;a:5]:[c:6]:[#7;a:7]:[c:8]:2:[c:9](=[O;D1;H0:10]):[n;H0;D3;+0:11](-[NH2;D1;+0:1]):[c:12]:1=[N;D1;H1:13] | null | [] | null | null | null | null | A solution of 2-imino-3-pentyl-1,2,3,7-tetrahydro-6h-purin-6-one (750 mg, 3.39 mmol) and 18 m of hydrazine in water (30 ml) was stirred at 150° C. for 30 min on a microwave reactor. The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine | Primary amine | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | c1ncc2[nH]cnc2n1 | Other | O | null | null | CCCCCn1c(=N)[nH]c(=O)c2[nH]cnc21.NN>O>CCCCCn1c(=N)n(N)c(=O)c2[nH]cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-746a3899625e484b9b62674d97b7a641 | CCCCCn1c(=N)n(N)c(=O)c2[nH]cnc21>>CCCCCn1c2nc[nH]c2c(=O)n2ncnc12 | NN1C(N(C=2N=CNC2C1=O)CCCCC)=N.C(OCC)([O-])[O-]>>C(CCCC)N1C=2N(C(C=3NC=NC13)=O)N=CN2 | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]([NH2:15])[c:18]1=[NH:17]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[n:15][cH:16][n:17][c:18]12 | CCCCCn1c(=N)n(N)c(=O)c2[nH]cnc21 | CCCCCn1c2nc[nH]c2c(=O)n2ncnc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 42583e3aaec0e678b7fe424f1573058d717f460b288147923b1c6f65cb69b8ec | 0c2e6cfe0bdb8f8cd78303a7637b3ef339f807f5bc27c4a22ad516ce20b37476 | O=c1c2[nH]cnc2[nH]c2ncnn12 | [#7;a:1]:[c:2]1:[c:3]:[#7;a:4](-[NH2;D1;+0:5]):[c;H0;D3;+0:6](=[NH;D1;+0:7]):[#7;a:8](-[C:9]):[c:10]:1:[#7;a:11]>>[#7;a:1]:[c:2]1:[c:3]:[#7;a:4]2:[n;H0;D2;+0:5]:[c:12]:[n;H0;D2;+0:7]:[c;H0;D3;+0:6]:2:[#7;a:8](-[C:9]):[c:10]:1:[#7;a:11] | 20.3 | [{"value": 20.0, "product": "C(CCCC)N1C=2N(C(C=3NC=NC13)=O)N=CN2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.3, "product": "C(CCCC)N1C=2N(C(C=3NC=NC13)=O)N=CN2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 6 | HOUR | The mixture of 1-amino-2-imino-3-pentyl-1,2,3,7-tetrahydro-6H-purin-6-one (0.10 g, 0.4 mmol) and ethyl orthoformate (5 mL, 30 mmol) was stirred at 100° C. for 6 hours. The reaction mixture was concentrated and purified by preparative LCMS to yield the desired product (20 mg, 20%). LCMS calculated for C11H15N6O(M+H): 24... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ncc2nc[nH]c2n1 | c1nc2nc3[nH]cnc3cn2n1 | c1nc2nc3[nH]cnc3cn2n1 | Other | null | 100 | 6 | CCCCCn1c(=N)n(N)c(=O)c2[nH]cnc21>>CCCCCn1c2nc[nH]c2c(=O)n2ncnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd5a6e849daf43f79ba7675cb3f849d4 | CCCCCn1c2nc[nH]c2c(=O)n2ncnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2ncnc12 | C(CCCC)N1C=2N(C(C=3NC=NC13)=O)N=CN2.BrN1C(CCC1=O)=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)N=CN3)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[n:16][cH:17][n:18][c:19]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2[n:16][cH:17][n:18][c:19]12 | CCCCCn1c2nc[nH]c2c(=O)n2ncnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2ncnc12 | null | null | O1CCCC1 | Functional Group Interconversion | Bromination | e711ed5c7fb7355144c6c6d25a210978a28c6ca3b2370bedf2b4f5d98ce282dc | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2ncnn12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]1:[c:4]:[c:5]2:[#7;a:6]:[cH;D2;+0:7]:[#7;a:8]:[c:9]:2:[#7;a:10](-[C:11]):[c:12]:1:[#7;a:13]>>[#7;a:2]:[#7;a:3]1:[c:4]:[c:5]2:[#7;a:6]:[c;H0;D3;+0:7](-[Br;H0;D1;+0:1]):[#7;a:8]:[c:9]:2:[#7;a:10](-[C:11]):[c:12]:1:[#7;a:13] | 12.4 | [{"value": 12.4, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)N=CN3)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 12.4, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)N=CN3)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 1 | HOUR | To the mixture of 4-pentyl-1,4-dihydro-9H-[1,2,4]triazolo[1,5-a]purin-9-one (19 mg, 0.077 mmol) in tetrahydrofuran (10 mL) was added N-bromosuccinimide (20 mg, 0.12 mol) at rt. The mixture was stirred at 70° C. for 1 hour. The mixture was concentrated and purified by preparative LCMS to yield the desired product (3.10 ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2nc3[nH]cnc3cn2n1.C1CCNC1 | c1nc2nc3[nH]cnc3cn2n1 | c1nc2nc3[nH]cnc3cn2n1 | HO- | O1CCCC1 | 70 | 1 | CCCCCn1c2nc[nH]c2c(=O)n2ncnc12.O=C1CCC(=O)N1Br>O1CCCC1>CCCCCn1c2nc(Br)[nH]c2c(=O)n2ncnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ec329f6c78014479a2009b41f7037f75 | COC(=O)CC(C)c1nc(-c2ccccc2)no1>>O=C(O)CCCc1nc(-c2ccccc2)no1 | Cl.C1(=CC=CC=C1)C1=NOC(=N1)C(CC(=O)OC)C.[OH-].[Na+].CO>>C1(=CC=CC=C1)C1=NOC(=N1)CCCC(=O)O | C[O:3][C:2](=[O:1])[CH2:4][CH:6]([CH3:5])[c:7]1[n:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][o:17]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][c:7]1[n:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[n:16][o:17]1 | COC(=O)CC(C)c1nc(-c2ccccc2)no1 | O=C(O)CCCc1nc(-c2ccccc2)no1 | null | null | null | Miscellaneous | OtherReaction | 16eb0e22715fadede32e44259800ac2375ae7dbc609f9ec677d59917bae07bec | b51da43dbb7140dac708518f8dbf83c5b067214819134afdb3f427285d08d6f8 | c1ccc(-c2ncon2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:4]-[CH;D3;+0:5](-[CH3;D1;+0:6])-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[#8;a:11]:1>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[CH2;D2;+0:4]-[CH2;D2;+0:6]-[CH2;D2;+0:5]-[c:7]1:[#7;a:8]:[c:9]:[#7;a:10]:[#8;a:11]:1 | 99 | [{"value": 99.0, "product": "C1(=CC=CC=C1)C1=NOC(=N1)CCCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of methyl 3-(3-phenyl-1,2,4-oxadiazol-5-yl)butanoate (1.53 g, 6.21 mmole) in methanol (10 ml) was added 1N NaOH (10 mL). After stirring at room temperature for 2 hours, the reaction solution was acidified to pH=3-4 with 6N HCl under an ice bath and then extracted with ethyl acetate three times. The combin... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ncon1.c1ccccc1 | Other | null | null | 2 | COC(=O)CC(C)c1nc(-c2ccccc2)no1>>O=C(O)CCCc1nc(-c2ccccc2)no1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-edc1fd367db644c7aaa6b540b0558972 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)CCCc1nc(-c2ccccc2)no1>>CCCCCn1/c(=N/NC(=O)CCCc2nc(-c3ccccc3)no2)[nH]c(=O)c2[nH]cnc21 | C1(=CC=CC=C1)C1=NOC(=N1)CCCC(=O)O.C(CCCC)N1/C(/NC(C=2NC=NC12)=O)=N/N.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C)N(CC)CC>>O=C1C=2NC=NC2N(\C(\N1)=N\NC(CCCC1=NC(=NO1)C1=CC=CC=C1)=O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH2:9])[nH:26][c:27](=[O:28])[c:29]2[nH:30][cH:31][n:32][c:33]12.O[C:10](=[O:11])[CH2:12][CH2:13][CH2:14][c:15]1[n:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:24][o:25]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH:9][C:10](=[O:11])[CH... | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)CCCc1nc(-c2ccccc2)no1 | CCCCCn1/c(=N/NC(=O)CCCc2nc(-c3ccccc3)no2)[nH]c(=O)c2[nH]cnc21 | null | null | O.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | e50d935ef072f0718d4e131af3df793f26e2f0a63884801973739584ab6e55ba | 2740512737e2508c1c8d407d0ee271fd1e1c46ad16223e8e2fc1e12936af0dea | O=C(CCCc1nc(-c2ccccc2)no1)N/N=c1\[nH]c(=O)c2[nH]cnc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]/[c:6](=[#7:7]\[NH2;D1;+0:8]):[#7;a:9]>>[#7;a:5]/[c:6](=[#7:7]\[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]):[#7;a:9] | 99.5 | [{"value": 99.0, "product": "O=C1C=2NC=NC2N(\\C(\\N1)=N\\NC(CCCC1=NC(=NO1)C1=CC=CC=C1)=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.5, "product": "O=C1C=2NC=NC2N(\\C(\\N1)=N\\NC(CCCC1=NC(=NO1)C1=CC=CC=C1)=O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 4-(3-phenyl-1,2,4-oxadiazol-5-yl)butanoic acid (1.44 g, 6.20 mmol), (2e)-3-pentyl-3,7-dihydro-1h-purine-2,6-dione 2-hydrazone (1.61 g, 6.82 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (3.02 g, 6.82 mmol) and triethylamine (1.73 ml, 12.4 mmol) in DMF (30 ml) was stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Carboxylic acid | Hydrazone amide | null | null | c1ncon1.c1ccccc1.c1ncc2[nH]cnc2n1 | HO- | O.CN(C)C=O | null | 8 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)CCCc1nc(-c2ccccc2)no1>O.CN(C)C=O>CCCCCn1/c(=N/NC(=O)CCCc2nc(-c3ccccc3)no2)[nH]c(=O)c2[nH]cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-104fb25fc2a046589e3c6ef947115662 | CCCCCn1/c(=N/NC(=O)CCCc2nc(-c3ccccc3)no2)[nH]c(=O)c2[nH]cnc21>>CCCCCn1c2nc[nH]c2c(=O)n2c(CCCc3nc(-c4ccccc4)no3)nnc12 | O=C1C=2NC=NC2N(\C(\N1)=N\NC(CCCC1=NC(=NO1)C1=CC=CC=C1)=O)CCCCC>>C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)CCCC2=NC(=NO2)C2=CC=CC=C2 | O=[C:15]([CH2:16][CH2:17][CH2:18][c:19]1[n:20][c:21](-[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[n:28][o:29]1)[NH:30]/[N:31]=[c:32]1/[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[nH:14]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])... | CCCCCn1/c(=N/NC(=O)CCCc2nc(-c3ccccc3)no2)[nH]c(=O)c2[nH]cnc21 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCCc3nc(-c4ccccc4)no3)nnc12 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | f919762557f16e8feb47c1fb62f203cd1ec4ed5f009cf276d2d0e0ec84ef6b80 | 78b0616e5760c6d4dadfc1fac5c58c0254d0dc7b1bf102fea4bc1349928b0776 | O=c1c2[nH]cnc2[nH]c2nnc(CCCc3nc(-c4ccccc4)no3)n12 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[NH;D2;+0:4]/[N;H0;D2;+0:5]=[c;H0;D3;+0:6]1\[nH;D2;+0:7]:[c:8](=[O;D1;H0:9]):[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:2:[#7;a:15]:1-[C:16]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:5]:[c;H0;D3;+0:6]2:[#7;a:15](-[C:16]):[c:14]3:[#7;a:13]:[c:12]:[#7;a:11]:[c:10]:3:[c:8](=[O;D... | 74 | [{"value": 74.0, "product": "C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)CCCC2=NC(=NO2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.8, "product": "C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)CCCC2=NC(=NO2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The mixture of N′-[(2E)-6-oxo-3-pentyl-1,3,6,7-tetrahydro-2H-purin-2-ylidene]-4-(3-phenyl-1,2,4-oxadiazol-5-yl)butanohydrazide (2.78 g, 6.17 mmol) in toluene (100 ml) was refluxed for 2 hours. After cooling to room temperature, the solid was filtered, washed with ethyl acetate/Hexane (1:9) and dried to give the desired... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide | null | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | c1ncon1.c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | C1(=CC=CC=C1)C | null | null | CCCCCn1/c(=N/NC(=O)CCCc2nc(-c3ccccc3)no2)[nH]c(=O)c2[nH]cnc21>C1(=CC=CC=C1)C>CCCCCn1c2nc[nH]c2c(=O)n2c(CCCc3nc(-c4ccccc4)no3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-118a8b47000742aebe0f51e7ea0e8e80 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCCc3nc(-c4ccccc4)no3)nnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCCc3nc(-c4ccccc4)no3)nnc12 | C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)CCCC2=NC(=NO2)C2=CC=CC=C2.BrN1C(CCC1=O)=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCCC3=NC(=NO3)C3=CC=CC=C3)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH2:17][CH2:18][CH2:19][c:20]3[n:21][c:22](-[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[n:29][o:30]3)[n:31][n:32][c:33]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11]... | CCCCCn1c2nc[nH]c2c(=O)n2c(CCCc3nc(-c4ccccc4)no3)nnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCCc3nc(-c4ccccc4)no3)nnc12 | null | null | C1CCOC1 | Functional Group Interconversion | Bromination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nnc(CCCc3nc(-c4ccccc4)no3)n12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | 21 | [{"value": 21.0, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCCC3=NC(=NO3)C3=CC=CC=C3)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 20.6, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCCC3=NC(=NO3)C3=CC=CC=C3)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 1 | HOUR | To the solution of 9-pentyl-3-[3-(3-phenyl-1,2,4-oxadiazol-5-yl)propyl]-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (0.50 g, 1.16 mmole) in THF (125 ml) at room temperature was added N-bromosuccinimide (0.309 g, 1.73 mmole). The mixture was stirred at 70° C. for 1 h. The mixture was concentrated and purified by pr... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1ncon1.c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | C1CCOC1 | 70 | 1 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCCc3nc(-c4ccccc4)no3)nnc12.O=C1CCC(=O)N1Br>C1CCOC1>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCCc3nc(-c4ccccc4)no3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-183ec978cfe24da39389a33fc446e25c | CCOC(=O)CCCBr.c1ccc(-c2cn[nH]c2)cc1>>CCOC(=O)CCCn1cc(-c2ccccc2)cn1 | BrCCCC(=O)OCC.C1(=CC=CC=C1)C=1C=NNC1.C(=O)([O-])[O-].[K+].[K+]>>C1(=CC=CC=C1)C=1C=NN(C1)CCCC(=O)OCC | Br[CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[nH:9]1[cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][n:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][n:9]1[cH:10][c:11](-[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[cH:18][n:19]1 | CCOC(=O)CCCBr.c1ccc(-c2cn[nH]c2)cc1 | CCOC(=O)CCCn1cc(-c2ccccc2)cn1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 31849359320dc3760d1a762ce95f120a544970fcb32b476aacf584ef81779a29 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(-c2cn[nH]c2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4](-[#8:5])=[O;D1;H0:6].[#7;a:7]1:[c:8]:[c:9]:[c:10]:[nH;D2;+0:11]:1>>[#8:5]-[C:4](=[O;D1;H0:6])-[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:11]1:[#7;a:7]:[c:8]:[c:9]:[c:10]:1 | 52 | [{"value": 52.0, "product": "C1(=CC=CC=C1)C=1C=NN(C1)CCCC(=O)OCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 13.8, "product": "C1(=CC=CC=C1)C=1C=NN(C1)CCCC(=O)OCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | The mixture of ethyl 4-bromobutyrate (0.400 g, 2.05 mmole), 4-phenyl-1H-pyrazole (0.296 g, 2.05 mmole) and K2CO3 (0.567 g, 4.10 mmole) in DMF (10 ml) was stirred at room temperature overnight. The reaction mixture was diluted with water (100 ml) and extracted with ethyl acetate (2×). The combined organic phases were wa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1 | HBr | O.CN(C)C=O | null | 8 | CCOC(=O)CCCBr.c1ccc(-c2cn[nH]c2)cc1>O.CN(C)C=O>CCOC(=O)CCCn1cc(-c2ccccc2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8caad14f2992442898e4732fb72846ce | CCOC(=O)CCCn1cc(-c2ccccc2)cn1>>O=C(O)CCCn1cc(-c2ccccc2)cn1 | C1(=CC=CC=C1)C=1C=NN(C1)CCCC(=O)OCC.Cl>>C1(=CC=CC=C1)C=1C=NN(C1)CCCC(=O)O | CC[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][n:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][n:17]1>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][n:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[cH:16][n:17]1 | CCOC(=O)CCCn1cc(-c2ccccc2)cn1 | O=C(O)CCCn1cc(-c2ccccc2)cn1 | null | null | CO.[OH-].[Na+] | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2cn[nH]c2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | 78 | [{"value": 78.0, "product": "C1(=CC=CC=C1)C=1C=NN(C1)CCCC(=O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.8, "product": "C1(=CC=CC=C1)C=1C=NN(C1)CCCC(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of ethyl 4-(4-phenyl-1H-pyrazol-1-yl)butanoate (273 mg, 1.06 mmole) in methanol (5 ml) and 1N NaOH (5 mL) was stirred at room temperature for 2 hours. The reaction mixture was adjusted to be acidic (pH=3-4) with 6 N HCl with an ice bath and then extracted with EtOAc (3×). The combined organic phases were wash... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1cn[nH]c1.c1ccccc1 | Other | CO.[OH-].[Na+] | null | 2 | CCOC(=O)CCCn1cc(-c2ccccc2)cn1>CO.[OH-].[Na+]>O=C(O)CCCn1cc(-c2ccccc2)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9d67097666cd49fda27b3a9639fe655d | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)CCCn1cc(-c2ccccc2)cn1>>CCCCCn1/c(=N/NC(=O)CCCn2cc(-c3ccccc3)cn2)[nH]c(=O)c2[nH]cnc21 | C1(=CC=CC=C1)C=1C=NN(C1)CCCC(=O)O.C(CCCC)N1/C(/NC(C=2NC=NC12)=O)=N/N.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C)N(CC)CC>>O=C1C=2NC=NC2N(\C(\N1)=N\NC(CCCN1N=CC(=C1)C1=CC=CC=C1)=O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH2:9])[nH:26][c:27](=[O:28])[c:29]2[nH:30][cH:31][n:32][c:33]12.O[C:10](=[O:11])[CH2:12][CH2:13][CH2:14][n:15]1[cH:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[cH:24][n:25]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH:9][C:10](=[O:11])[... | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)CCCn1cc(-c2ccccc2)cn1 | CCCCCn1/c(=N/NC(=O)CCCn2cc(-c3ccccc3)cn2)[nH]c(=O)c2[nH]cnc21 | null | null | CN(C)C=O.CCOC(=O)C | Acylation | Carboxylic acid with primary amine to amide | e50d935ef072f0718d4e131af3df793f26e2f0a63884801973739584ab6e55ba | 2740512737e2508c1c8d407d0ee271fd1e1c46ad16223e8e2fc1e12936af0dea | O=C(CCCn1cc(-c2ccccc2)cn1)N/N=c1\[nH]c(=O)c2[nH]cnc2[nH]1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[#7;a:5]/[c:6](=[#7:7]\[NH2;D1;+0:8]):[#7;a:9]>>[#7;a:5]/[c:6](=[#7:7]\[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4]):[#7;a:9] | 99.7 | [{"value": 99.7, "product": "O=C1C=2NC=NC2N(\\C(\\N1)=N\\NC(CCCN1N=CC(=C1)C1=CC=CC=C1)=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "O=C1C=2NC=NC2N(\\C(\\N1)=N\\NC(CCCN1N=CC(=C1)C1=CC=CC=C1)=O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 4-(4-phenyl-1H-pyrazol-1-yl)butanoic acid (190 mg, 0.825 mmol), (2E)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (195.0 mg, 0.825 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (401 mg, 0.908 mmol) and triethyl amine (0.23 ml, 1.65 mmol) in DMF (10 ml) was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Carboxylic acid | Hydrazone amide | null | null | c1cn[nH]c1.c1ccccc1.c1ncc2[nH]cnc2n1 | HO- | CN(C)C=O.CCOC(=O)C | null | 8 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=C(O)CCCn1cc(-c2ccccc2)cn1>CN(C)C=O.CCOC(=O)C>CCCCCn1/c(=N/NC(=O)CCCn2cc(-c3ccccc3)cn2)[nH]c(=O)c2[nH]cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6add9091aa554342a6b67c226dcccd55 | CCCCCn1/c(=N/NC(=O)CCCn2cc(-c3ccccc3)cn2)[nH]c(=O)c2[nH]cnc21>>CCCCCn1c2nc[nH]c2c(=O)n2c(CCCn3cc(-c4ccccc4)cn3)nnc12 | O=C1C=2NC=NC2N(\C(\N1)=N\NC(CCCN1N=CC(=C1)C1=CC=CC=C1)=O)CCCCC>>C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)CCCN2N=CC(=C2)C2=CC=CC=C2 | O=[C:15]([CH2:16][CH2:17][CH2:18][n:19]1[cH:20][c:21](-[c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[cH:28][n:29]1)[NH:30]/[N:31]=[c:32]1/[n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[nH:14]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13... | CCCCCn1/c(=N/NC(=O)CCCn2cc(-c3ccccc3)cn2)[nH]c(=O)c2[nH]cnc21 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCCn3cc(-c4ccccc4)cn3)nnc12 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | f919762557f16e8feb47c1fb62f203cd1ec4ed5f009cf276d2d0e0ec84ef6b80 | 78b0616e5760c6d4dadfc1fac5c58c0254d0dc7b1bf102fea4bc1349928b0776 | O=c1c2[nH]cnc2[nH]c2nnc(CCCn3cc(-c4ccccc4)cn3)n12 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[NH;D2;+0:4]/[N;H0;D2;+0:5]=[c;H0;D3;+0:6]1\[nH;D2;+0:7]:[c:8](=[O;D1;H0:9]):[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:2:[#7;a:15]:1-[C:16]>>[C:3]-[C:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:5]:[c;H0;D3;+0:6]2:[#7;a:15](-[C:16]):[c:14]3:[#7;a:13]:[c:12]:[#7;a:11]:[c:10]:3:[c:8](=[O;D... | 66 | [{"value": 66.0, "product": "C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)CCCN2N=CC(=C2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 66.0, "product": "C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)CCCN2N=CC(=C2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of N′-[(2E)-6-oxo-3-pentyl-1,3,6,7-tetrahydro-2H-purin-2-ylidene]-4-(4-phenyl-1H-pyrazol-1-yl)butanohydrazide (369 mg, 0.823 mmols) in toluene (20 ml) was refluxed for 2 hours. After cooling to room temperature, the solid formed was filtered, washed with EtOAc/Hexane (1:9) and dried to give the desired produc... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone amide | null | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | c1cn[nH]c1.c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | C1(=CC=CC=C1)C | null | null | CCCCCn1/c(=N/NC(=O)CCCn2cc(-c3ccccc3)cn2)[nH]c(=O)c2[nH]cnc21>C1(=CC=CC=C1)C>CCCCCn1c2nc[nH]c2c(=O)n2c(CCCn3cc(-c4ccccc4)cn3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eb3b578650aa424188ad18c782068849 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCCn3cc(-c4ccccc4)cn3)nnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCCn3cc(-c4ccccc4)cn3)nnc12 | C(CCCC)N1C=2N(C(C=3NC=NC13)=O)C(=NN2)CCCN2N=CC(=C2)C2=CC=CC=C2.BrN1C(CCC1=O)=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCCN3N=CC(=C3)C3=CC=CC=C3)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH2:17][CH2:18][CH2:19][n:20]3[cH:21][c:22](-[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[cH:29][n:30]3)[n:31][n:32][c:33]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:1... | CCCCCn1c2nc[nH]c2c(=O)n2c(CCCn3cc(-c4ccccc4)cn3)nnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCCn3cc(-c4ccccc4)cn3)nnc12 | null | null | C1CCOC1 | Functional Group Interconversion | Bromination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nnc(CCCn3cc(-c4ccccc4)cn3)n12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | 38.3 | [{"value": 38.0, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCCN3N=CC(=C3)C3=CC=CC=C3)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 38.3, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCCN3N=CC(=C3)C3=CC=CC=C3)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 1 | HOUR | To a solution of 9-pentyl-3-[3-(4-phenyl-1H-pyrazol-1-yl)propyl]-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (234 mg, 0.543 mmol) in THF (45 ml) at room temperature was added N-bromosuccinimide (145 mg, 0.814 mmol). After stirring at 70° C. for 1 hour, the reaction mixture was concentrated and then purified by pre... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1cn[nH]c1.c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | C1CCOC1 | 70 | 1 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCCn3cc(-c4ccccc4)cn3)nnc12.O=C1CCC(=O)N1Br>C1CCOC1>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCCn3cc(-c4ccccc4)cn3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a302dec015f0498c9b6d3a146f377c91 | CCOC(CCC#N)OCC.NO>>CCOC(CCC(=N)NO)OCC | C(C)OC(CCC#N)OCC.Cl.NO.C([O-])(O)=O.[Na+]>>C(C)OC(CCC(NO)=N)OCC | [CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH2:6][C:7]#[N:8])[O:11][CH2:12][CH3:13].[NH2:9][OH:10]>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][CH2:6][C:7](=[NH:8])[NH:9][OH:10])[O:11][CH2:12][CH3:13] | CCOC(CCC#N)OCC.NO | CCOC(CCC(=N)NO)OCC | null | null | CO | Heteroatom Alkylation and Arylation | N-hydroxyimidamide from nitrile and hydroxylamine | 08a01a2d1cd9346f7b3dddbfcbf8124b349e5763794287a4a1b9ee287b4d6aa7 | 38c3b778e04536ea6155ce05fc7c4746354a32b3703099defb07490833e3a961 | null | [C:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[NH;D1;+0:4])-[NH;D2;+0:5]-[O;D1;H1:6] | null | [] | null | null | null | null | A mixture of 4,4-diethoxybutanenitrile (5.0 g, 32 mmol), hydroxylamine hydrochloride (2.4 g, 35 mmol) and sodium bicarbonate (2.9 g, 35 mmol) in methanol (50 mL) was refluxed for 5 hours. After cooling to room temperature, the reaction mixture was concentrated and the residue was diluted with EtOAc and water. The water... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Primary amine | Secondary amine | null | null | null | null | CO | null | null | CCOC(CCC#N)OCC.NO>CO>CCOC(CCC(=N)NO)OCC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0ffafafad429422ba97c1c4487ecc9de | COc1ccc(-c2nc(CCC=O)no2)cc1.NN=C1N=C2N=CN=C2C(=O)N1>>CCCCCn1c2nc[nH]c2c(=O)n2c(CCc3noc(-c4ccc(OC)cc4)n3)nnc12 | N1C(N=C2N=CN=C2C1=O)=NN.COC1=CC=C(C=C1)C1=NC(=NO1)CCC=O>>COC1=CC=C(C=C1)C1=NC(=NO1)CCC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O | O=[CH:15][CH2:16][CH2:17][c:18]1[n:19][o:20][c:21](-[c:22]2[cH:1][cH:24][c:25]([O:26][CH3:27])[cH:28][cH:29]2)[n:30]1.[N:6]1=[C:7]2[N:8]=[CH:9][N:10]=[C:11]2[C:12](=[O:13])[NH:14][C:33]1=[N:32][NH2:31]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15]([CH2:16][CH2:17]... | COc1ccc(-c2nc(CCC=O)no2)cc1.NN=C1N=C2N=CN=C2C(=O)N1 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCc3noc(-c4ccc(OC)cc4)n3)nnc12 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 415438373b6c89916fe944451ebcf68817e04ded21a5bf5b90912a794744bab3 | e6db118b5f632ca02d9e1ba56495e2a40001ccce13c863dabe2bbdda22b66d26 | O=c1c2[nH]cnc2[nH]c2nnc(CCc3noc(-c4ccccc4)n3)n12 | O=[CH;D2;+0:1]-[C:2]-[C:3]-[c:4]1:[#7;a:5]:[#8;a:6]:[c:7](-[c;H0;D3;+0:8]2:[c:9]:[c:10]:[c:11](-[#8:12]):[cH;D2;+0:13]:[cH;D2;+0:14]:2):[#7;a:15]:1.[NH2;D1;+0:16]-[N;H0;D2;+0:17]=[C;H0;D3;+0:18]1-[N;H0;D2;+0:19]=[C;H0;D3;+0:20]2-[N;H0;D2;+0:21]=[CH;D2;+0:22]-[N;H0;D2;+0:23]=[C;H0;D3;+0:24]-2-[C;H0;D3;+0:25](=[O;D1;H0:2... | 95.4 | [{"value": 64.0, "product": "COC1=CC=C(C=C1)C1=NC(=NO1)CCC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.4, "product": "COC1=CC=C(C=C1)C1=NC(=NO1)CCC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 1H-purine-2,6-dione 2-hydrazone (680 mg, 2.88 mmol) and 3-[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]propanal (900 mg, 3.88 mmol) in ethanol (20 mL) was refluxed for 4 hours. The reaction mixture was concentrated and the residue was mixed with acetic acid (10 mL). The resulting mixture was refluxed for 3 ho... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Aldehyde.Substituted imine.Secondary amide | null | c1ccccc1.C1=NC2=NCNCC2=N1 | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | c1ncon1.c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | null | C(C)O | null | null | COc1ccc(-c2nc(CCC=O)no2)cc1.NN=C1N=C2N=CN=C2C(=O)N1>C(C)O>CCCCCn1c2nc[nH]c2c(=O)n2c(CCc3noc(-c4ccc(OC)cc4)n3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6eb5ef580e5a4a8f893463dc31a9c088 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCc3noc(-c4ccc(OC)cc4)n3)nnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCc3noc(-c4ccc(OC)cc4)n3)nnc12 | COC1=CC=C(C=C1)C1=NC(=NO1)CCC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O.BrN1C(CCC1=O)=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCC3=NOC(=N3)C3=CC=C(C=C3)OC)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH2:17][CH2:18][c:19]3[n:20][o:21][c:22](-[c:23]4[cH:24][cH:25][c:26]([O:27][CH3:28])[cH:29][cH:30]4)[n:31]3)[n:32][n:33][c:34]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])... | CCCCCn1c2nc[nH]c2c(=O)n2c(CCc3noc(-c4ccc(OC)cc4)n3)nnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCc3noc(-c4ccc(OC)cc4)n3)nnc12 | null | null | CN(C)C=O | Functional Group Interconversion | Bromination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nnc(CCc3noc(-c4ccccc4)n3)n12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | null | [] | 70 | CELSIUS | 1 | HOUR | To a solution of 3-2-[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]ethyl-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (160 mg, 0.36 mmol) in DMF (15 mL) at room temperature was added N-bromosuccinimide (110 mg, 0.61 mmol). After stirring at 70° C. for 1 hour, the reaction mixture was concentrated and purified ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1ncon1.c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | CN(C)C=O | 70 | 1 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCc3noc(-c4ccc(OC)cc4)n3)nnc12.O=C1CCC(=O)N1Br>CN(C)C=O>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCc3noc(-c4ccc(OC)cc4)n3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee410f0fc6fe409099a58bd6e12bfbf4 | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCc3noc(-c4ccc(OC)cc4)n3)nnc12>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCc3noc(-c4ccc(O)cc4)n3)nnc12 | BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCC3=NOC(=N3)C3=CC=C(C=C3)OC)CCCCC.B(Br)(Br)Br>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCC3=NOC(=N3)C3=CC=C(C=C3)O)CCCCC | C[O:27][c:26]1[cH:25][cH:24][c:23](-[c:22]2[o:21][n:20][c:19]([CH2:18][CH2:17][c:16]3[n:15]4[c:13](=[O:14])[c:12]5[c:7]([n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:33]4[n:32][n:31]3)[n:8][c:9]([Br:10])[nH:11]5)[n:30]2)[cH:29][cH:28]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:1... | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCc3noc(-c4ccc(OC)cc4)n3)nnc12 | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCc3noc(-c4ccc(O)cc4)n3)nnc12 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=c1c2[nH]cnc2[nH]c2nnc(CCc3noc(-c4ccccc4)n3)n12 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | To a solution of 7-bromo-3-2-[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]ethyl-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (190 mg, 0.36 mmol) in CH2Cl2 (12 mL) was added a solution of BBr3 in CH2Cl2 (1 M, 7.0 ml, 7.0 mmol) at room temperature. After stirring at room temperature overnight, the reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ncon1.c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | Other | C(Cl)Cl | null | 8 | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCc3noc(-c4ccc(OC)cc4)n3)nnc12>C(Cl)Cl>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCc3noc(-c4ccc(O)cc4)n3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ea40a2eea40b4c0abae5aec9b060ced3 | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=CCCNC(=O)OCc1ccccc1>>CCCCCn1/c(=N/N=C\CCNC(=O)OCc2ccccc2)[nH]c(=O)c2[nH]cnc21 | C(CCCC)N1/C(/NC(C=2NC=NC12)=O)=N/N.O=CCCNC(OCC1=CC=CC=C1)=O>>O=C1C=2NC=NC2N(\C(\N1)=N\N=C/CCNC(OCC1=CC=CC=C1)=O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[NH2:9])[nH:24][c:25](=[O:26])[c:27]2[nH:28][cH:29][n:30][c:31]12.O=[CH:10][CH2:11][CH2:12][NH:13][C:14](=[O:15])[O:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1/[c:7](=[N:8]/[N:9]=[CH:10]\[CH2:11][CH2:12][NH:13][... | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=CCCNC(=O)OCc1ccccc1 | CCCCCn1/c(=N/N=C\CCNC(=O)OCc2ccccc2)[nH]c(=O)c2[nH]cnc21 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 369b3f62a39edf615315b2761263eb1b649612c7b3caef083e9b41e01b478de5 | a492f13607987389cdd7ab2f9f1199c71d7d1e56ec2df1828d06f8b8bbe23769 | O=C(NCC/C=N\N=c1/[nH]c(=O)c2[nH]cnc2[nH]1)OCc1ccccc1 | O=[CH;D2;+0:1]-[C:2]-[C:3].[#7;a:4]/[c:5](=[#7:6]\[NH2;D1;+0:7]):[#7;a:8]>>[#7;a:4]/[c:5](=[#7:6]\[N;H0;D2;+0:7]=[CH;D2;+0:1]/[C:2]-[C:3]):[#7;a:8] | 97.9 | [{"value": 58.0, "product": "O=C1C=2NC=NC2N(\\C(\\N1)=N\\N=C/CCNC(OCC1=CC=CC=C1)=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.9, "product": "O=C1C=2NC=NC2N(\\C(\\N1)=N\\N=C/CCNC(OCC1=CC=CC=C1)=O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of (2E)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (2.3 g, 9.6 mmol) and benzyl (3-oxopropyl)carbamate (2.0 g, 9.6 mmol) in ethanol (30 mL) was refluxed overnight. The reaction mixture was concentrated to give the product (4.0 g, 58% yield), which was used for next step without further purification.... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Aldehyde | null | null | null | c1ccccc1.c1ncc2[nH]cnc2n1 | HO- | C(C)O | null | null | CCCCCn1/c(=N/N)[nH]c(=O)c2[nH]cnc21.O=CCCNC(=O)OCc1ccccc1>C(C)O>CCCCCn1/c(=N/N=C\CCNC(=O)OCc2ccccc2)[nH]c(=O)c2[nH]cnc21 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1d540088b85c478584e758869c1dcc48 | CCCCCn1/c(=N/N=C\CCNC(=O)OCc2ccccc2)[nH]c(=O)c2[nH]cnc21>>CCCCCn1c2nc[nH]c2c(=O)n2c(CCNC(=O)OCc3ccccc3)nnc12 | O=C1C=2NC=NC2N(\C(\N1)=N\N=C/CCNC(OCC1=CC=CC=C1)=O)CCCCC>>O=C1C=2NC=NC2N(C=2N1C(=NN2)CCNC(OCC2=CC=CC=C2)=O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[nH:14]/[c:31]1=[N:30]\[N:29]=[CH:15]/[CH2:16][CH2:17][NH:18][C:19](=[O:20])[O:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:1... | CCCCCn1/c(=N/N=C\CCNC(=O)OCc2ccccc2)[nH]c(=O)c2[nH]cnc21 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCNC(=O)OCc3ccccc3)nnc12 | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 066077903128dcf5e3d8c17f71c894783195993eb8e78fea83753934f8800b97 | 42048ba06e684767e79a864f38d2ee087b4547e971032cda3c892dd210eef093 | O=C(NCCc1nnc2[nH]c3nc[nH]c3c(=O)n12)OCc1ccccc1 | [C:1]-[C:2]/[CH;D2;+0:3]=[N;H0;D2;+0:4]\[N;H0;D2;+0:5]=[c;H0;D3;+0:6]1/[nH;D2;+0:7]:[c:8](=[O;D1;H0:9]):[c:10]2:[#7;a:11]:[c:12]:[#7;a:13]:[c:14]:2:[#7;a:15]:1-[C:16]>>[C:1]-[C:2]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:5]:[c;H0;D3;+0:6]2:[#7;a:15](-[C:16]):[c:14]3:[#7;a:13]:[c:12]:[#7;a:11]:[c:10]:3:[c:8](=[O;D1;H0... | 54.8 | [{"value": 54.0, "product": "O=C1C=2NC=NC2N(C=2N1C(=NN2)CCNC(OCC2=CC=CC=C2)=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 54.8, "product": "O=C1C=2NC=NC2N(C=2N1C(=NN2)CCNC(OCC2=CC=CC=C2)=O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of benzyl (3Z)-3-[(2E)-(6-oxo-3-pentyl-1,3,6,7-tetrahydro-2H-purin-2-ylidene)hydrazono]propylcarbamate (4.0 g, 5.6 mmol) in acetic acid (50 mL) was refluxed in the air overnight. The mixture was concentrated and purified by preparative LCMS to give the desired product (1.3 g, 54% yield) as a white solid. LCMS... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ncc2nc[nH]c2n1 | c1nc2cn3cnnc3nc2[nH]1 | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | null | C(C)(=O)O | null | null | CCCCCn1/c(=N/N=C\CCNC(=O)OCc2ccccc2)[nH]c(=O)c2[nH]cnc21>C(C)(=O)O>CCCCCn1c2nc[nH]c2c(=O)n2c(CCNC(=O)OCc3ccccc3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fa626a7c0a53495abf1710c96a707653 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCNC(=O)OCc3ccccc3)nnc12>>CCCCCn1c2nc[nH]c2c(=O)n2c(CCN)nnc12 | O=C1C=2NC=NC2N(C=2N1C(=NN2)CCNC(OCC2=CC=CC=C2)=O)CCCCC>>NCCC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O | O=C(OCc1ccccc1)[NH:18][CH2:17][CH2:16][c:15]1[n:14]2[c:12](=[O:13])[c:11]3[c:7]([n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:21]2[n:20][n:19]1)[n:8][cH:9][nH:10]3>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:10][c:11]2[c:12](=[O:13])[n:14]2[c:15]([CH2:16][CH2:17][NH2:18])[n:19][n:20][c:21]12 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCNC(=O)OCc3ccccc3)nnc12 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCN)nnc12 | null | [Pd] | CO | Reduction | Hydrogenolysis of amides/imides/carbamates | 087b6600ba91d3df931fe6979f2445c192cbfd59e04fd2d8a10f7c7573ac669f | 4e549866ec1acadec4c84aaf8495992a28ec78d8ea5ef1b9f44dd843b0dcb7d4 | O=c1c2[nH]cnc2[nH]c2nncn12 | O=C(-O-C-c1:c:c:c:c:c:1)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 92.2 | [{"value": 90.0, "product": "NCCC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.2, "product": "NCCC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of benzyl [2-(5-oxo-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-3-yl)ethyl]carbamate (0.52 g, 1.2 mmol) in methanol (50 mL) was added 10% Pd/C (100 mg). The reaction mixture was shaken in a hydrogenation reactor under 50 Psi H2 for 3 hours. The reaction mixture was filtered through a pad of celite... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether | Primary amine | c1ccccc1 | null | c1nc2cn3cnnc3nc2[nH]1 | HO- | [Pd].CO | null | null | CCCCCn1c2nc[nH]c2c(=O)n2c(CCNC(=O)OCc3ccccc3)nnc12>[Pd].CO>CCCCCn1c2nc[nH]c2c(=O)n2c(CCN)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-30bcb777201b43de839009bee00a8066 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCN)nnc12.O=C1CCC(=O)N1Br>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCN)nnc12 | NCCC1=NN=C2N1C(C=1NC=NC1N2CCCCC)=O.BrN1C(CCC1=O)=O>>NCCC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)Br)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][cH:9][nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH2:17][CH2:18][NH2:19])[n:20][n:21][c:22]12.O=C1CCC(=O)N1[Br:10]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH2:17][CH2:18][NH2:19])[n:20][n:21][c:22... | CCCCCn1c2nc[nH]c2c(=O)n2c(CCN)nnc12.O=C1CCC(=O)N1Br | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCN)nnc12 | null | null | C1CCOC1 | Functional Group Interconversion | Bromination | ec99ea20e93d70158a8c5b88a0324c2920957b29ee02a6abc4d48c347d7daa1b | 0e444576b73669992a4073cc3f7b10ed52cb9df09f9f8e4042e39e6a602aa390 | O=c1c2[nH]cnc2[nH]c2nncn12 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[cH;D2;+0:9]:[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13]>>[#7;a:2]:[#7;a:3]:[c:4]1:[#7;a:5]:[c:6]:[c:7]2:[#7;a:8]:[c;H0;D3;+0:9](-[Br;H0;D1;+0:1]):[#7;a:10]:[c:11]:2:[#7;a:12]:1-[C:13] | 76 | [{"value": 76.0, "product": "NCCC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)Br)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.1, "product": "NCCC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)Br)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 1 | HOUR | To a mixture of 3-(2-aminoethyl)-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (310 mg, 1.1 mmol) in THF (50 mL), was added N-Bromosuccinimide (0.29 g, 1.6 mmol). The mixture was stirred at 70° C. for 1 hour. The reaction mixture was concentrated. The solid was filtered and washed with EtOAc to yield the de... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Aromatic halide | c1nc2cn3cnnc3nc2[nH]1.C1CCNC1 | c1nc2cn3cnnc3nc2[nH]1 | c1nc2cn3cnnc3nc2[nH]1 | HO- | C1CCOC1 | 70 | 1 | CCCCCn1c2nc[nH]c2c(=O)n2c(CCN)nnc12.O=C1CCC(=O)N1Br>C1CCOC1>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCN)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-fc36eedd2d934f338ea7fb8ac31ec2ef | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCN)nnc12.COc1ccc(C(=O)O)cc1>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCNC(=O)c3ccc(OC)cc3)nnc12 | NCCC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)Br)=O.COC1=CC=C(C(=O)O)C=C1.F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C.C(C)N(CC)CC>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCNC(C3=CC=C(C=C3)OC)=O)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH2:17][CH2:18][NH2:19])[n:30][n:31][c:32]12.O[C:20](=[O:21])[c:22]1[cH:23][cH:24][c:25]([O:26][CH3:27])[cH:28][cH:29]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[... | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCN)nnc12.COc1ccc(C(=O)O)cc1 | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCNC(=O)c3ccc(OC)cc3)nnc12 | null | null | O.C(C)#N.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCc1nnc2[nH]c3nc[nH]c3c(=O)n12)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 73 | [{"value": 73.0, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCNC(C3=CC=C(C=C3)OC)=O)CCCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.7, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCNC(C3=CC=C(C=C3)OC)=O)CCCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 3-(2-aminoethyl)-7-bromo-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (70 mg, 0.20 mmol), 4-methoxybenzoic acid (32 mg, 0.21 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (92 mg, 0.21 mmol), and triethylamine (0.053 mL, 0.38 mmol) in DMF (5 mL) was stirred at ro... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | HO- | O.C(C)#N.CN(C)C=O | null | 8 | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCN)nnc12.COc1ccc(C(=O)O)cc1>O.C(C)#N.CN(C)C=O>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCNC(=O)c3ccc(OC)cc3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-18d292e8812a4a5cbb73d639cd1ee844 | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCN)nnc12.O=C=Nc1ccccc1>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCNC(=O)Nc3ccccc3)nnc12 | NCCC1=NN=C2N1C(C=1NC(=NC1N2CCCCC)Br)=O.C1(=CC=CC=C1)N=C=O>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCNC(=O)NC3=CC=CC=C3)CCCCC | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:15]2[c:16]([CH2:17][CH2:18][NH2:19])[n:29][n:30][c:31]12.[C:20](=[O:21])=[N:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n:... | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCN)nnc12.O=C=Nc1ccccc1 | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCNC(=O)Nc3ccccc3)nnc12 | null | null | O.C(C)#N.CN(C)C=O | Acylation | Urea synthesis via isocyanate and primary amine | d39cd7dc52a79bb265ff8ef61ef7bf9dc7f7b5fb0150fcb4881bdfb18ab9c380 | a5dc801930c765d2a435a0a2973e50163c305ba8e7641d6adbcc1550b7b96de7 | O=C(NCCc1nnc2[nH]c3nc[nH]c3c(=O)n12)Nc1ccccc1 | [C:1]-[C:2]-[NH2;D1;+0:3].[O;D1;H0:4]=[C;H0;D2;+0:5]=[N;H0;D2;+0:6]-[c:7](:[c:8]):[c:9]>>[C:1]-[C:2]-[NH;D2;+0:3]-[C;H0;D3;+0:5](=[O;D1;H0:4])-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9] | 80 | [{"value": 80.0, "product": "BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCNC(=O)NC3=CC=CC=C3)CCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 3-(2-aminoethyl)-7-bromo-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-5-one (62 mg, 0.17 mmol) and phenyl isocyanate (0.018 mL, 0.16 mmol) in DMF (5 mL) was stirred at room temperature overnight. The reaction mixture was diluted with water and acetonitrile and then purified by preparative LCMS to gi... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate.Primary amine | Urea | null | null | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | null | O.C(C)#N.CN(C)C=O | null | 8 | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCN)nnc12.O=C=Nc1ccccc1>O.C(C)#N.CN(C)C=O>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCNC(=O)Nc3ccccc3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f77f09454d8640f9bf014e4ad2eb415f | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCNC(=O)c3ccc(OC)cc3)nnc12>>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCNC(=O)c3ccc(O)cc3)nnc12 | BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCNC(C3=CC=C(C=C3)OC)=O)CCCCC.B(Br)(Br)Br>>BrC1=NC=2N(C=3N(C(C2N1)=O)C(=NN3)CCNC(C3=CC=C(C=C3)O)=O)CCCCC | C[O:26][c:25]1[cH:24][cH:23][c:22]([C:20]([NH:19][CH2:18][CH2:17][c:16]2[n:15]3[c:13](=[O:14])[c:12]4[c:7]([n:6]([CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[c:31]3[n:30][n:29]2)[n:8][c:9]([Br:10])[nH:11]4)=[O:21])[cH:28][cH:27]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[c:7]2[n:8][c:9]([Br:10])[nH:11][c:12]2[c:13](=[O:14])[n... | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCNC(=O)c3ccc(OC)cc3)nnc12 | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCNC(=O)c3ccc(O)cc3)nnc12 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(NCCc1nnc2[nH]c3nc[nH]c3c(=O)n12)c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | To a solution of N-[2-(7-bromo-5-oxo-9-pentyl-6,9-dihydro-5H-[1,2,4]triazolo[4,3-a]purin-3-yl)ethyl]-4-methoxybenzamide (63.0 mg, 0.125 mmol) in CH2Cl2 (5 mL) at 0° C. was added a solution of Boron tribromide in CH2Cl2 (1.0 M, 1.3 mL, 1.3 mmol). The mixture was stirred at room temperature overnight. The reaction mixtur... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1nc2cn3cnnc3nc2[nH]1 | Other | C(Cl)Cl | null | 8 | CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCNC(=O)c3ccc(OC)cc3)nnc12>C(Cl)Cl>CCCCCn1c2nc(Br)[nH]c2c(=O)n2c(CCNC(=O)c3ccc(O)cc3)nnc12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4ab0fe31746f4de89f022f8d6cc85a9d | CC(C)(N)CCn1cnnc1.CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1>>COC(=O)c1cc(C(=O)C=NC(C)(C)CCn2cnnc2)ccc1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=C(C(=O)OC)C=C(C=C1)C(C(O)OCC)=O.CC(CCN1C=NN=C1)(C)N>>C(C1=CC=CC=C1)OC1=C(C(=O)OC)C=C(C=C1)C(C=NC(CCN1C=NN=C1)(C)C)=O | [NH2:11][C:12]([CH3:13])([CH3:14])[CH2:15][CH2:16][n:17]1[cH:18][n:19][n:20][cH:21]1.CCO[CH:10](O)[C:8]([c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:24]([O:25][CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[cH:23][cH:22]1)=[O:9]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([C:8](=[O:9])[CH:10]=[N:11][C:12]([CH3:1... | CC(C)(N)CCn1cnnc1.CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1 | COC(=O)c1cc(C(=O)C=NC(C)(C)CCn2cnnc2)ccc1OCc1ccccc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 9f630e6c2b6d7517a3fa7357236cf4ddfd17dba1b594cd96ae8996ff5f3995d6 | 62cc0e6b65becc601a2e48497b9a7abf308c36c68e35364f9fb60106ecf6b8b5 | O=C(C=NCCCn1cnnc1)c1ccc(OCc2ccccc2)cc1 | C-C-O-[CH;D3;+0:1](-O)-[C:2](=[O;D1;H0:3])-[c:4].[C:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[NH2;D1;+0:9]>>[C:5]-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[N;H0;D2;+0:9]=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | 16 g of methyl 2-benzyloxy-5-(2-ethoxy-2-hydroxy-acetyl)-benzoate and 6 g of 1,1-dimethyl-3-[1,2,4]triazol-4-yl-propylamine are heated to 70° C. for one hour in 100 mL ethanol. Then half the solvent is distilled off and the mixture remaining is cooled. The product that crystallises out is suction filtered and washed wi... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Secondary alcohol.Primary amine | Ketone.Substituted imine | null | null | c1ccccc1.c1nnc[nH]1.c1ccccc1 | HO- | C(C)O | null | null | CC(C)(N)CCn1cnnc1.CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1>C(C)O>COC(=O)c1cc(C(=O)C=NC(C)(C)CCn2cnnc2)ccc1OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-25c24f0e1d404431b21b22ec9c290112 | COC(=O)c1cc(C(=O)CNC(C)(C)CCn2cnnc2)ccc1OCc1ccccc1>>CC(C)(CCn1cnnc1)NCC(O)c1ccc(OCc2ccccc2)c(CO)c1 | CC(=O)C.[Cl-].[Ca+2].[Cl-].C(C1=CC=CC=C1)OC1=C(C(=O)OC)C=C(C=C1)C(CNC(CCN1C=NN=C1)(C)C)=O.[BH4-].[Na+]>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C(CNC(CCN1C=NN=C1)(C)C)O)CO | CO[C:28]([c:27]1[c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:17][cH:16][c:15]([C:13]([CH2:12][NH:11][C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][n:6]2[cH:7][n:8][n:9][cH:10]2)=[O:14])[cH:30]1)=[O:29]>>[CH3:1][C:2]([CH3:3])([CH2:4][CH2:5][n:6]1[cH:7][n:8][n:9][cH:10]1)[NH:11][CH2:12][CH:13]([OH:14])[c:1... | COC(=O)c1cc(C(=O)CNC(C)(C)CCn2cnnc2)ccc1OCc1ccccc1 | CC(C)(CCn1cnnc1)NCC(O)c1ccc(OCc2ccccc2)c(CO)c1 | null | null | O1CCCC1.C(C)(=O)O.C(C)O | Reduction | OtherReaction | 67089bd4b5ba61d4201285032d065b7dbb074f27b1058a42daae9f0677a26309 | fb0acaa903b6e5b1d95989a91fad01e909b2ecc65b96c636622bf14cc20a64c2 | c1ccc(COc2ccc(CCNCCCn3cnnc3)cc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]:[c:6](-[C;H0;D3;+0:7](=[O;H0;D1;+0:8])-[C:9]-[#7:10]):[c:11]>>[#7:10]-[C:9]-[CH;D3;+0:7](-[OH;D1;+0:8])-[c:6](:[c:11]):[c:5]:[c:3](-[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:4] | null | [] | 5 | CELSIUS | 8 | HOUR | 5 g of calcium chloride are dissolved in 50 mL ethanol. Then 10 g of methyl 2-benzyloxy-5-[2-(1,1-dimethyl-3-[1,2,4]triazol-4-yl-propylamino)-acetyl]-benzoate in 100 mL tetrahydrofuran are added and the mixture is cooled to 5° C. It is combined batchwise with 3.5 g of sodium borohydride and stirred overnight while heat... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Primary alcohol.Secondary alcohol | null | null | c1nnc[nH]1.c1ccccc1.c1ccccc1 | Other | O1CCCC1.C(C)(=O)O.C(C)O | 5 | 8 | COC(=O)c1cc(C(=O)CNC(C)(C)CCn2cnnc2)ccc1OCc1ccccc1>O1CCCC1.C(C)(=O)O.C(C)O>CC(C)(CCn1cnnc1)NCC(O)c1ccc(OCc2ccccc2)c(CO)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a6850de313434d4bbf3726e7f136eee8 | CC(=O)OC(CNC(C)(C)CCn1cnnc1)c1ccc(OCc2ccccc2)c(CO)c1>>CC(C)(CCn1cnnc1)NCC(O)c1ccc(O)c(CO)c1 | C(C)(=O)OC(CNC(CCN1C=NN=C1)(C)C)C1=CC(=C(C=C1)OCC1=CC=CC=C1)CO.[H][H]>>CC(CCN1C=NN=C1)(C)NCC(O)C1=CC(=C(C=C1)O)CO | CC(=O)[O:14][CH:13]([CH2:12][NH:11][C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][n:6]1[cH:7][n:8][n:9][cH:10]1)[c:15]1[cH:16][cH:17][c:18]([O:19]Cc2ccccc2)[c:20]([CH2:21][OH:22])[cH:23]1>>[CH3:1][C:2]([CH3:3])([CH2:4][CH2:5][n:6]1[cH:7][n:8][n:9][cH:10]1)[NH:11][CH2:12][CH:13]([OH:14])[c:15]1[cH:16][cH:17][c:18]([OH:19])[c:20]... | CC(=O)OC(CNC(C)(C)CCn1cnnc1)c1ccc(OCc2ccccc2)c(CO)c1 | CC(C)(CCn1cnnc1)NCC(O)c1ccc(O)c(CO)c1 | null | [Pd] | CO | Reduction | OtherReaction | 5191c2a4aa54a541316ab8da2c23088325133ca5b0a78ef65048e93be8ca25c3 | 34ee45d408c5a96781b888def3a5f72b571220140037e25fd3d3fe11cbb09ec2 | c1ccc(CCNCCCn2cnnc2)cc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2](-[C:3])-[c:4].[c:5]:[c:6](-[O;H0;D2;+0:7]-C-c1:c:c:c:c:c:1):[c:8]>>[C:3]-[C:2](-[OH;D1;+0:1])-[c:4].[OH;D1;+0:7]-[c:6](:[c:5]):[c:8] | null | [] | null | null | null | null | 5 g of 1-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-(1,1-dimethyl-3-[1,2,4]triazol-4-yl-propylamino)-ethanol acetate are hydrogenated with 0.5 g of palladium on charcoal (5%) in 100 mL methanol. After the theoretically calculated amount of hydrogen has been taken up the catalyst is filtered off and the filtrate is evaporat... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether | Secondary alcohol.Aromatic alcohol | c1ccccc1 | null | c1nnc[nH]1.c1ccccc1 | HO- | [Pd].CO | null | null | CC(=O)OC(CNC(C)(C)CCn1cnnc1)c1ccc(OCc2ccccc2)c(CO)c1>[Pd].CO>CC(C)(CCn1cnnc1)NCC(O)c1ccc(O)c(CO)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9f34e6e3d751450c9ab46d4ded2de53c | CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1.COc1ccc(-c2nc(C)n(CCC(C)(C)N)n2)cc1>>COC(=O)c1cc(C(O)CNC(C)(C)CCn2nc(-c3ccc(OC)cc3)nc2C)ccc1OCc1ccccc1 | CC(=O)C.C(C1=CC=CC=C1)OC1=C(C(=O)OC)C=C(C=C1)C(C(O)OCC)=O.COC1=CC=C(C=C1)C1=NN(C(=N1)C)CCC(C)(C)N.[BH4-].[Na+]>>C(C1=CC=CC=C1)OC1=C(C(=O)OC)C=C(C=C1)C(CNC(CCN1N=C(N=C1C)C1=CC=C(C=C1)OC)(C)C)O | CCO[CH:10](O)[C:8]([c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:33]([O:34][CH2:35][c:36]2[cH:37][cH:38][cH:39][cH:40][cH:41]2)[cH:32][cH:31]1)=[O:9].[NH2:11][C:12]([CH3:13])([CH3:14])[CH2:15][CH2:16][n:17]1[n:18][c:19](-[c:20]2[cH:21][cH:22][c:23]([O:24][CH3:25])[cH:26][cH:27]2)[n:28][c:29]1[CH3:30]>>[CH3:1][O:2][C:3... | CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1.COc1ccc(-c2nc(C)n(CCC(C)(C)N)n2)cc1 | COC(=O)c1cc(C(O)CNC(C)(C)CCn2nc(-c3ccc(OC)cc3)nc2C)ccc1OCc1ccccc1 | null | null | C(C)(=O)O.C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 1fdebd18d8e186352a5054d1639a246066c291a759c2941bdb27defc05ab0b96 | 270f718637e505454980bf4a24a04f3a3a166f4d4160855797b4e1923ac25b66 | c1ccc(COc2ccc(CCNCCCn3cnc(-c4ccccc4)n3)cc2)cc1 | C-C-O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[NH2;D1;+0:11]>>[C:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[NH;D2;+0:11]-[CH2;D2;+0:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4](:[c:5]):[c:6] | null | [] | 10 | CELSIUS | 3 | HOUR | 8.5 g of methyl 2-benzyloxy-5-(2-ethoxy-2-hydroxy-acetyl)-benzoate and 4.9 g of 3-[3-(4-methoxy-phenyl)-5-methyl-[1,2,4]triazol-1-yl]-1,1-dimethyl-propylamine in 100 mL ethanol are stirred for three hours at 60° C., cooled to 10° C., combined batchwise with 0.8 g of sodium borohydride and stirred for a further three ho... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Secondary alcohol.Primary amine | Secondary alcohol.Secondary amine | null | null | c1ccccc1.c1nc[nH]n1.c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C(C)O | 10 | 3 | CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1.COc1ccc(-c2nc(C)n(CCC(C)(C)N)n2)cc1>C(C)(=O)O.C(C)O>COC(=O)c1cc(C(O)CNC(C)(C)CCn2nc(-c3ccc(OC)cc3)nc2C)ccc1OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d146b460d3904465aaaa50ff037c40c0 | COc1ccc(-c2nc(C)n(CCC(C)(C)NCC(O)c3ccc(OCc4ccccc4)c(CO)c3)n2)cc1>>COc1ccc(-c2nc(C)n(CCC(C)(C)NCC(O)c3ccc(O)c(CO)c3)n2)cc1 | C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C(CNC(CCN1N=C(N=C1C)C1=CC=C(C=C1)OC)(C)C)O)CO>>OC(CNC(CCN1N=C(N=C1C)C1=CC=C(C=C1)OC)(C)C)C1=CC(=C(C=C1)O)CO | c1ccc(C[O:25][c:24]2[cH:23][cH:22][c:21]([CH:19]([CH2:18][NH:17][C:14]([CH2:13][CH2:12][n:11]3[c:9]([CH3:10])[n:8][c:7](-[c:6]4[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:32][cH:31]4)[n:30]3)([CH3:15])[CH3:16])[OH:20])[cH:29][c:26]2[CH2:27][OH:28])cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][c:9]([CH3:10])[n:11]([CH2:1... | COc1ccc(-c2nc(C)n(CCC(C)(C)NCC(O)c3ccc(OCc4ccccc4)c(CO)c3)n2)cc1 | COc1ccc(-c2nc(C)n(CCC(C)(C)NCC(O)c3ccc(O)c(CO)c3)n2)cc1 | null | [Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(CCNCCCn2cnc(-c3ccccc3)n2)cc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | null | null | 5 g of 1-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-{3-[3-(4-methoxy-phenyl)-5-methyl-[1,2,4]triazol-1-yl]-1,1-dimethyl-propylamino}-ethanol dissolved in 100 mL methanol are hydrogenated under normal pressure with 1 g of palladium on charcoal (5%) as catalyst. Then the catalyst is separated off and the filtrate is evaporat... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1nnc[nH]1.c1ccccc1 | Other | [Pd].CO | null | null | COc1ccc(-c2nc(C)n(CCC(C)(C)NCC(O)c3ccc(OCc4ccccc4)c(CO)c3)n2)cc1>[Pd].CO>COc1ccc(-c2nc(C)n(CCC(C)(C)NCC(O)c3ccc(O)c(CO)c3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0b6542bca0fa4b02977893324d8e1da7 | COC(=O)c1cc(C(O)CNC(C)(C)CCN2C=CN(c3ccc(OC)cc3)C2)ccc1OCc1ccccc1>>COc1ccc(N2C=CN(CCC(C)(C)NCC(O)c3ccc(OCc4ccccc4)c(CO)c3)C2)cc1 | C(C1=CC=CC=C1)OC1=C(C(=O)OC)C=C(C=C1)C(CNC(CCN1CN(C=C1)C1=CC=C(C=C1)OC)(C)C)O.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C(CNC(CCN1CN(C=C1)C1=CC=C(C=C1)OC)(C)C)O)CO | CO[C:33]([c:32]1[c:23]([O:24][CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[cH:22][cH:21][c:20]([CH:18]([CH2:17][NH:16][C:13]([CH2:12][CH2:11][N:10]2[CH:9]=[CH:8][N:7]([c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:38][cH:37]3)[CH2:36]2)([CH3:14])[CH3:15])[OH:19])[cH:35]1)=[O:34]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N... | COC(=O)c1cc(C(O)CNC(C)(C)CCN2C=CN(c3ccc(OC)cc3)C2)ccc1OCc1ccccc1 | COc1ccc(N2C=CN(CCC(C)(C)NCC(O)c3ccc(OCc4ccccc4)c(CO)c3)C2)cc1 | null | null | O1CCCC1.C(C)O | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | C1=CN(c2ccccc2)CN1CCCNCCc1ccc(OCc2ccccc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 12 | HOUR | 13 g of methyl 2-benzyloxy-5-(1-hydroxy-2-{3-[3-(4-methoxy-phenyl)-imidazol-1-yl]-1,1-dimethyl-propylamino}-ethyl)-benzoate in 100 mL tetrahydrofuran are reacted with a solution of 6.5 g of calcium chloride in 65 mL ethanol and 4.5 g of sodium borohydride analogously to the method used for Example 1c. After a reaction ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.C1=C[NH]C[NH]1.c1ccccc1.c1ccccc1 | Other | O1CCCC1.C(C)O | null | 12 | COC(=O)c1cc(C(O)CNC(C)(C)CCN2C=CN(c3ccc(OC)cc3)C2)ccc1OCc1ccccc1>O1CCCC1.C(C)O>COc1ccc(N2C=CN(CCC(C)(C)NCC(O)c3ccc(OCc4ccccc4)c(CO)c3)C2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-009ab4f6f1204a8daf3f600ee93a5576 | COC(=O)c1cc(C(O)CNC(C)(C)CCn2cnc(-c3ccc(OC)cc3)n2)ccc1OCc1ccccc1>>COc1ccc(-c2ncn(CCC(C)(C)NCC(O)c3ccc(OCc4ccccc4)c(CO)c3)n2)cc1 | C(C1=CC=CC=C1)OC1=C(C(=O)OC)C=C(C=C1)C(CNC(CCN1N=C(N=C1)C1=CC=C(C=C1)OC)(C)C)O.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C(CNC(CCN1N=C(N=C1)C1=CC=C(C=C1)OC)(C)C)O)CO | CO[C:33]([c:32]1[c:23]([O:24][CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[cH:22][cH:21][c:20]([CH:18]([CH2:17][NH:16][C:13]([CH2:12][CH2:11][n:10]2[cH:9][n:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:38][cH:37]3)[n:36]2)([CH3:14])[CH3:15])[OH:19])[cH:35]1)=[O:34]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7... | COC(=O)c1cc(C(O)CNC(C)(C)CCn2cnc(-c3ccc(OC)cc3)n2)ccc1OCc1ccccc1 | COc1ccc(-c2ncn(CCC(C)(C)NCC(O)c3ccc(OCc4ccccc4)c(CO)c3)n2)cc1 | null | null | O1CCCC1.C(C)O | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(COc2ccc(CCNCCCn3cnc(-c4ccccc4)n3)cc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 7.3 g of methyl 2-benzyloxy-5-(1-hydroxy-2-{3-[3-(4-methoxy-phenyl)-[1,2,4]triazol-1-yl]-1,1-dimethyl-propylamino}-ethyl)-benzoate are placed in 100 mL tetrahydrofuran and reduced with a total of 6.8 g of calcium chloride dissolved in ethanol and 4.6 g of sodium borohydride as described for Example 1c. The product is o... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1nnc[nH]1.c1ccccc1.c1ccccc1 | Other | O1CCCC1.C(C)O | null | null | COC(=O)c1cc(C(O)CNC(C)(C)CCn2cnc(-c3ccc(OC)cc3)n2)ccc1OCc1ccccc1>O1CCCC1.C(C)O>COc1ccc(-c2ncn(CCC(C)(C)NCC(O)c3ccc(OCc4ccccc4)c(CO)c3)n2)cc1 |
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