dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3913574c5e754f0a906e2d6dcd271a96 | COC(=O)c1cc(-c2ccccc2)nn(CC(C)C)c1=O>>CC(C)Cn1nc(-c2ccccc2)cc(C(=O)O)c1=O | C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C(C(C)C)N1N=C(C=C(C1=O)C(=O)OC)C1=CC=CC=C1>>C(=O)(O)C=1C(N(N=C(C1)C1=CC=CC=C1)CC(C)C)=O | C[O:18][C:16]([c:15]1[cH:14][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:19]1=[O:20])=[O:17]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]([C:16](=[O:17])[OH:18])[c:19]1=[O:20] | COC(=O)c1cc(-c2ccccc2)nn(CC(C)C)c1=O | CC(C)Cn1nc(-c2ccccc2)cc(C(=O)O)c1=O | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccccc2)n[nH]1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 82.5 | [{"value": 82.5, "product": "C(=O)(O)C=1C(N(N=C(C1)C1=CC=CC=C1)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (7), 2-isobutyl-4-methoxycarbonyl-6-phenyl-2H-pyridazin-3-one was reacted to yield the title compound as colorless fine-needles (yield: 82.5%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccnnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(-c2ccccc2)nn(CC(C)C)c1=O>>CC(C)Cn1nc(-c2ccccc2)cc(C(=O)O)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-85d77cad6d7d4fc6a9967b37a5758965 | CC(C)Cn1nc(-c2ccccc2)cc(C(=O)O)c1=O>>CC(C)Cn1nc(-c2ccccc2)cc(CO)c1=O | FC=1C=C(C=CC1C)C=1C(=C(C(N(N1)CC(C)C)=O)O)C.C(=O)(O)C=1C(N(N=C(C1)C1=CC=CC=C1)CC(C)C)=O>>OCC=1C(N(N=C(C1)C1=CC=CC=C1)CC(C)C)=O | O=[C:16]([c:15]1[cH:14][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:18]1=[O:19])[OH:17]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]([CH2:16][OH:17])[c:18]1=[O:19] | CC(C)Cn1nc(-c2ccccc2)cc(C(=O)O)c1=O | CC(C)Cn1nc(-c2ccccc2)cc(CO)c1=O | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)n[nH]1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10]>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:9]:1=[O;D1;H0:10] | 22.3 | [{"value": 22.3, "product": "OCC=1C(N(N=C(C1)C1=CC=CC=C1)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-carboxy-2-isobutyl-6-phenyl-2H-pyridazin-3-one was reacted to yield the title compound as colorless fine-needles (yield: 22.3%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccnnc1.c1ccccc1 | Other | null | null | null | CC(C)Cn1nc(-c2ccccc2)cc(C(=O)O)c1=O>>CC(C)Cn1nc(-c2ccccc2)cc(CO)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ac14e02261ea4cb49fe34891bbbfb985 | CC(C)Cn1nc(-c2ccccc2)cc(CO)c1=O.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F>>CC(C)Cn1nc(-c2ccccc2)cc(COS(C)(=O)=O)c1=O | FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.OCC=1C(N(N=C(C1)C1=CC=CC=C1)CC(C)C)=O>>C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=CC=C1 | CC(C)Cn1nc(-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)cc(CO)c1=O.Cc1ccc(-[c:7]2[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:22](=[O:23])[c:15]([CH2:16][O:17][S:18]([CH3:19])(=[O:20])=[O:21])[cH:14]2)cc1F>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]([CH2:16][O:17... | CC(C)Cn1nc(-c2ccccc2)cc(CO)c1=O.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F | CC(C)Cn1nc(-c2ccccc2)cc(COS(C)(=O)=O)c1=O | null | null | null | C-C Coupling | OtherReaction | 2098b64217db572fd21ffa1641d0218783f6c9e021fde10467d50db3d229fd5e | af1238a0d333620701e826be7a9367863896c568351b293f0287634647ec2581 | O=c1ccc(-c2ccccc2)n[nH]1 | C-C(-C)-C-n1:n:c(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):c:c(-C-O):c:1=O.C-c1:c:c:c(-[c;H0;D3;+0:6]2:[#7;a:7]:[#7;a:8](-[C:9]):[c:10]:[c:11]:[c:12]:2):c:c:1-F>>[C:9]-[#7;a:8]1:[#7;a:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:12]:[c:11]:[c:10]:1 | 68.4 | [{"value": 68.4, "product": "C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (9), 4-hydroxymethyl-2-isobutyl-6-phenyl-2H-pyridazin-3-one was reacted to yield the title compound as colorless fine-needles (yield: 68.4%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | null | c1ccnnc1.c1ccccc1.c1ccccc1.c1ccnnc1 | c1ccnnc1.c1ccccc1 | c1ccnnc1.c1ccccc1 | HF | null | null | null | CC(C)Cn1nc(-c2ccccc2)cc(CO)c1=O.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F>>CC(C)Cn1nc(-c2ccccc2)cc(COS(C)(=O)=O)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3644b3e033524ed4a71bf1b7ba9b6fa0 | CC(C)Cn1nc(-c2ccccc2)cc(OS(C)(=O)=O)c1=O.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1c(-c2ccccc2)nn(CC(C)C)c(=O)c1N1CCN(C(=O)OC(C)(C)C)CC1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C(C(C)C)N1N=C(C=C(C1=O)OS(=O)(=O)C)C1=CC=CC=C1.N1(CCNCC1)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC=CC=C1)CC(C)C)=O | CC(C)Cn1nc(-[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)cc(OS(C)(=O)=O)c1=O.Cc1ccc(-[c:3]2[c:2]([CH3:1])[c:18]([N:19]3[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]3)[c:16](=[O:17])[n:11]([CH2:12][CH:13]([CH3:14])[CH3:15])[n:10]2)cc1F>>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][cH... | CC(C)Cn1nc(-c2ccccc2)cc(OS(C)(=O)=O)c1=O.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F | Cc1c(-c2ccccc2)nn(CC(C)C)c(=O)c1N1CCN(C(=O)OC(C)(C)C)CC1 | null | null | CN(C=O)C | C-C Coupling | OtherReaction | 569ad7e4900714ae8996d7f91669649d97471c2d715a14882668da30740ac9a3 | 4798f927b0d0a447933af42550b8eee742ad3485466c208bb5acfef30902fee4 | O=c1[nH]nc(-c2ccccc2)cc1N1CCNCC1 | C-C(-C)-C-n1:n:c(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):c:c(-O-S(-C)(=O)=O):c:1=O.C-c1:c:c:c(-[c;H0;D3;+0:6]2:[#7;a:7]:[#7;a:8](-[C:9]):[c:10]:[c:11]:[c:12]:2-[C;D1;H3:13]):c:c:1-F>>[C:9]-[#7;a:8]1:[#7;a:7]:[c;H0;D3;+0:6](-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):[c:12](-[C;D1;H3:13]):[c:11]:[c:10]:1 | 83.5 | [{"value": 83.5, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC=CC=C1)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-isobutyl-4-methanesulfonyloxy-6-phenyl-2H-pyridazin-3-one and tert-butyl 1-piperazinecarboxylate were reacted in N,N-dimethylformamide as a solvent to yield the title compound as a yellow oil (yield: 83.5%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic halide | null | c1ccnnc1.c1ccccc1.c1ccccc1.c1ccnnc1 | c1ccnnc1.c1ccccc1 | c1ccnnc1.c1ccccc1.C1C[NH]CC[NH]1 | MsOH.HF | CN(C=O)C | null | null | CC(C)Cn1nc(-c2ccccc2)cc(OS(C)(=O)=O)c1=O.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>CN(C=O)C>Cc1c(-c2ccccc2)nn(CC(C)C)c(=O)c1N1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-40b31dad112f477da22ae7c8e274bb70 | CC(C)Cn1nc(-c2ccccc2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1c(-c2ccccc2)nn(CC(C)C)c(=O)c1N1CCN(C)CC1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=CC=C1.CN1CCNCC1>>C(C(C)C)N1N=C(C(=C(C1=O)N1CCN(CC1)C)C)C1=CC=CC=C1 | CS(=O)(=O)OC[c:18]1[cH:2][c:3](-[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[n:10][n:11]([CH2:12][CH:13]([CH3:14])[CH3:15])[c:16]1=[O:17].[NH:19]1[CH2:20][CH2:21][N:22]([CH3:23])[CH2:24][CH2:25]1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2[CH3:1])cc1F>>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][cH:7][cH:8][cH:9]2)[n:1... | CC(C)Cn1nc(-c2ccccc2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F | Cc1c(-c2ccccc2)nn(CC(C)C)c(=O)c1N1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2a0dbc48e846de8e0c36eabe2ecaa3dda67e2c62a942dd827dcb6cda2589c033 | f8979a7dc32618975f84bf1d08d0eb1a0766a30fc7e3bcdfee8ffc6d86d4188b | O=c1[nH]nc(-c2ccccc2)cc1N1CCNCC1 | C-C(-C)-C-n1:n:c(-c2:c:c:c(-C):c(-F):c:2):c(-[CH3;D1;+0:1]):c(-N2-C-C-N(-C(=O)-O-C(-C)(-C)-C)-C-C-2):c:1=O.C-S(=O)(=O)-O-C-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c:4](-[c:5]):[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:4](-[c:5]):[c;H0;D3;+0:3]... | 77.1 | [{"value": 77.1, "product": "C(C(C)C)N1N=C(C(=C(C1=O)N1CCN(CC1)C)C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-isobutyl-4-methanesulfonyloxymethyl-6-phenyl-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 77.1%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic halide.Carbamic ester.Ether.Secondary amine.Tertiary amine.Boc | Tertiary amine | c1ccnnc1.C1CNCC[NH]1.c1ccccc1.c1ccnnc1.C1CNCCN1 | c1ccnnc1.C1C[NH]CC[NH]1 | c1ccnnc1.c1ccccc1.C1C[NH]CC[NH]1 | MsOH.HF | null | null | null | CC(C)Cn1nc(-c2ccccc2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1c(-c2ccccc2)nn(CC(C)C)c(=O)c1N1CCN(C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-df11df326a664c738828444ae4c6bfdd | CC(C)Cn1nc(-c2ccccc2)cc(COS(C)(=O)=O)c1=O.CNC>>CC(C)Cn1nc(-c2ccccc2)cc(CN(C)C)c1=O | C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=CC=C1.CNC>>CN(C)CC=1C(N(N=C(C1)C1=CC=CC=C1)CC(C)C)=O | CS(=O)(=O)O[CH2:16][c:15]1[cH:14][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:20]1=[O:21].[NH:17]([CH3:18])[CH3:19]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:14][c:15]([CH2:16][N:17]([CH3:18])[CH3:19])[c:20]1=[O:21] | CC(C)Cn1nc(-c2ccccc2)cc(COS(C)(=O)=O)c1=O.CNC | CC(C)Cn1nc(-c2ccccc2)cc(CN(C)C)c1=O | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1ccc(-c2ccccc2)n[nH]1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C;D1;H3:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:11](-[C;D1;H3:10])-[C;D1;H3:12]):[c:8]:1=[O;D1;H0:9] | 81.1 | [{"value": 81.1, "product": "CN(C)CC=1C(N(N=C(C1)C1=CC=CC=C1)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 7, 2-isobutyl-4-methanesulfonyloxymethyl-6-phenyl-2H-pyridazin-3-one and dimethylamine were reacted to yield the title compound as a yellow oil (yield: 81.1%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccnnc1.c1ccccc1 | MsOH.HO- | null | null | null | CC(C)Cn1nc(-c2ccccc2)cc(COS(C)(=O)=O)c1=O.CNC>>CC(C)Cn1nc(-c2ccccc2)cc(CN(C)C)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8a650fee2ff8484493b5687f5a40859d | Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1F>>Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1 | C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C(C(C)C)N1N=C(C=C(C1=O)C(=O)OC)C1=CC=C(C=C1)C>>C(=O)(O)C=1C(N(N=C(C1)C1=CC=C(C=C1)C)CC(C)C)=O | F[c:21]1[c:2]([CH3:1])[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12](=[O:13])[n:14]([CH2:15][CH:16]([CH3:17])[CH3:18])[n:19]2)[cH:20]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12](=[O:13])[n:14]([CH2:15][CH:16]([CH3:17])[CH3:18])[n:19]2)[cH:20][cH:21]1 | Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1F | Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1 | null | null | null | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=c1ccc(-c2ccccc2)n[nH]1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6]>>[C;D1;H3:5]-[c:4](:[c:6]):[cH;D2;+0:1]:[c:2]:[c:3] | 86.7 | [{"value": 86.7, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (7), 2-isobutyl-4-methoxycarbonyl-6-(4-methylphenyl)-2H-pyridazin-3-one was reacted to yield the title compound as slightly yellow needles (yield: 86.7%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccnnc1 | Other | null | null | null | Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1F>>Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c276e1f8025c489e94c3d89be8644b2f | Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1>>Cc1ccc(-c2cc(CO)c(=O)n(CC(C)C)n2)cc1 | FC=1C=C(C=CC1C)C=1C(=C(C(N(N1)CC(C)C)=O)O)C.C(=O)(O)C=1C(N(N=C(C1)C1=CC=C(C=C1)C)CC(C)C)=O>>OCC=1C(N(N=C(C1)C1=CC=C(C=C1)C)CC(C)C)=O | O=[C:9]([c:8]1[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:20][cH:19]2)[n:18][n:13]([CH2:14][CH:15]([CH3:16])[CH3:17])[c:11]1=[O:12])[OH:10]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][OH:10])[c:11](=[O:12])[n:13]([CH2:14][CH:15]([CH3:16])[CH3:17])[n:18]2)[cH:19][cH:20]1 | Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1 | Cc1ccc(-c2cc(CO)c(=O)n(CC(C)C)n2)cc1 | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)n[nH]1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10]>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:9]:1=[O;D1;H0:10] | 46 | [{"value": 46.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-carboxy-2-isobutyl-6-(4-methylphenyl)-2H-pyridazin-3-one was reacted to yield the title compound as slightly yellow needles (yield: 46.0%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccnnc1 | Other | null | null | null | Cc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1>>Cc1ccc(-c2cc(CO)c(=O)n(CC(C)C)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-74de9776ad1442dcae9e4f6f0674c3b5 | Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F>>Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1 | FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.OC=1C(N(N=C(C1C)C1=CC=C(C=C1)C)CC(C)C)=O>>C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)C | F[c:24]1[c:2]([CH3:1])[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][O:10][S:11]([CH3:12])(=[O:13])=[O:14])[c:15](=[O:16])[n:17]([CH2:18][CH:19]([CH3:20])[CH3:21])[n:22]2)[cH:23]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][O:10][S:11]([CH3:12])(=[O:13])=[O:14])[c:15](=[O:16])[n:17]([CH2:18][CH:19]([CH3:20... | Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F | Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1 | null | null | null | Functional Group Interconversion | Aromatic dehalogenation | b66818d3926a4463fb8e1c3d4a89e94e47b4d46960d4bdb7bcfbeeec427cfd4e | 56de34d4a44cb25d9380269ee5e138b0f24b40a3a0db22c5508049dc775a861f | O=c1ccc(-c2ccccc2)n[nH]1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C;D1;H3:5]):[c:6]>>[C;D1;H3:5]-[c:4](:[c:6]):[cH;D2;+0:1]:[c:2]:[c:3] | 87.4 | [{"value": 87.4, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (9), 4-hydroxy-methyl-2-isobutyl-6-(4-methylphenyl)-2H-pyridazin-3-one was reacted to yield the title compound as slightly yellow needles (yield: 87.4%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccnnc1 | Other | null | null | null | Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F>>Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-50745821803a42088dfeb550ab166f5e | Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1.c1ccc(CN2CCNCC2)cc1>>Cc1ccc(-c2cc(CN3CCN(Cc4ccccc4)CC3)c(=O)n(CC(C)C)n2)cc1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)C.C(C1=CC=CC=C1)N1CCNCC1>>C(C1=CC=CC=C1)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC=C(C=C1)C)CC(C)C)=O | CS(=O)(=O)O[CH2:9][c:8]1[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:32][cH:31]2)[n:30][n:25]([CH2:26][CH:27]([CH3:28])[CH3:29])[c:23]1=[O:24].[NH:10]1[CH2:11][CH2:12][N:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[CH2:21][CH2:22]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][N:10]3[CH2:11... | Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1.c1ccc(CN2CCNCC2)cc1 | Cc1ccc(-c2cc(CN3CCN(Cc4ccccc4)CC3)c(=O)n(CC(C)C)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1[nH]nc(-c2ccccc2)cc1CN1CCN(Cc2ccccc2)CC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 97.7 | [{"value": 97.7, "product": "C(C1=CC=CC=C1)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC=C(C=C1)C)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-isobutyl-4-methanesulfonyloxymethyl-6-(4-methylphenyl)-2H-pyridazin-3-one and 1-benzylpiperazine were reacted to yield the title compound as a pale yellow oil (yield: 97.7%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.c1ccccc1 | MsOH.HO- | null | null | null | Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1.c1ccc(CN2CCNCC2)cc1>>Cc1ccc(-c2cc(CN3CCN(Cc4ccccc4)CC3)c(=O)n(CC(C)C)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c487c0012f194e2b89c578acace2c975 | CNC.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1>>Cc1ccc(-c2cc(CN(C)C)c(=O)n(CC(C)C)n2)cc1 | C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)C.CNC>>CN(C)CC=1C(N(N=C(C1)C1=CC=C(C=C1)C)CC(C)C)=O | [NH:10]([CH3:11])[CH3:12].CS(=O)(=O)O[CH2:9][c:8]1[cH:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:22][cH:21]2)[n:20][n:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[c:13]1=[O:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][c:8]([CH2:9][N:10]([CH3:11])[CH3:12])[c:13](=[O:14])[n:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[n:20]2)... | CNC.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1 | Cc1ccc(-c2cc(CN(C)C)c(=O)n(CC(C)C)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1ccc(-c2ccccc2)n[nH]1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C;D1;H3:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:11](-[C;D1;H3:10])-[C;D1;H3:12]):[c:8]:1=[O;D1;H0:9] | 96.6 | [{"value": 96.6, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 7, 2-isobutyl-4-methanesulfonyloxymethyl-6-(4-methylphenyl)-2H-pyridazin-3-one and dimethylamine were reacted to yield the title compound as a slightly yellow oil (yield: 96.6%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccnnc1 | MsOH.HO- | null | null | null | CNC.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1>>Cc1ccc(-c2cc(CN(C)C)c(=O)n(CC(C)C)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3a3c9318f6ac4f7f9a67a326862e69ad | CCNCC.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1>>CCN(CC)Cc1cc(-c2ccc(C)cc2)nn(CC(C)C)c1=O | C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)C.C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)C.C(C)NCC>>C(C)N(CC)CC=1C(N(N=C(C1)C1=CC=C(C=C1)C)CC(C)C)=O | [CH3:1][CH2:2][NH:3][CH2:4][CH3:5].CS(=O)(=O)O[CH2:6][c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]2)[n:17][n:18]([CH2:19][CH:20]([CH3:21])[CH3:22])[c:23]1=[O:24]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]2)[n:17][n:18]([CH2:... | CCNCC.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1 | CCN(CC)Cc1cc(-c2ccc(C)cc2)nn(CC(C)C)c1=O | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1ccc(-c2ccccc2)n[nH]1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C;D1;H3:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C;D1;H3:14]>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:12](-[C:11]-[C;D1;H3:10])-[C:13]-[C;D1;H3:14]):[c:8]:1=[O;D1;H0:9] | 95 | [{"value": 95.0, "product": "C(C)N(CC)CC=1C(N(N=C(C1)C1=CC=C(C=C1)C)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 9 (4), 2-isobutyl-4-methanesulfonyloxymethyl-6-(4-methylphenyl)-2H-pyridazin-3-one and diethylamine were reacted to yield the title compound as a pale yellow oil (yield: 95.0%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccnnc1.c1ccccc1 | MsOH.HO- | null | null | null | CCNCC.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1>>CCN(CC)Cc1cc(-c2ccc(C)cc2)nn(CC(C)C)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c911fd7775ee4fb784d12a182bdc5b96 | CN.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1>>CNCc1cc(-c2ccc(C)cc2)nn(CC(C)C)c1=O | CN.C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)C.C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)C>>C(C(C)C)N1N=C(C=C(C1=O)CNC)C1=CC=C(C=C1)C | [CH3:1][NH2:2].CS(=O)(=O)O[CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH3:11])[cH:12][cH:13]2)[n:14][n:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[c:20]1=[O:21]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([CH3:11])[cH:12][cH:13]2)[n:14][n:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[c:20]1=[O:21] | CN.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1 | CNCc1cc(-c2ccc(C)cc2)nn(CC(C)C)c1=O | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | 8445343b2fb2fd8a9bc06f8532794f2ba6b99565a6e05a3bb9a4344ce2671186 | 7e6303acde8be57b43b4c6a673e1c7537b1efde90f08932e09e153dbba53a700 | O=c1ccc(-c2ccccc2)n[nH]1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C;D1;H3:10]-[NH2;D1;+0:11]>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:11]-[C;D1;H3:10]):[c:8]:1=[O;D1;H0:9] | 94.5 | [{"value": 94.5, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 9 (4), 2-isobutyl-4-methanesulfonyloxymethyl-6-(4-methylphenyl)-2H-pyridazin-3-one and methylamine were reacted to yield the title compound as a slightly yellow oil (yield: 94.5%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Primary amine | Secondary amine | null | null | c1ccnnc1.c1ccccc1 | MsOH.HO- | null | null | null | CN.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1>>CNCc1cc(-c2ccc(C)cc2)nn(CC(C)C)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7e8c7a02041841ee99d759e10a103f84 | CCOC(=O)C(O)(CC(=O)c1ccc(C(F)(F)F)cc1)C(=O)OCC.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1>>O=C(O)c1cc(-c2ccc(C(F)(F)F)cc2)n[nH]c1=O | C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)C.C(C)OC(=O)C(C(=O)OCC)(CC(=O)C1=CC=C(C=C1)C(F)(F)F)O>>C(=O)(O)C=1C(NN=C(C1)C1=CC=C(C=C1)C(F)(F)F)=O | CCOC(=O)C(O)(CC(=O)c1c[cH:15][c:10]([C:11]([F:12])([F:13])[F:14])[cH:9][cH:8]1)C(OCC)=[O:1].Cc1cc[c:7](-[c:6]2[cH:5][c:4]([CH2:2][O:3]S(C)(=O)=O)[c:19](=[O:20])[n:18](CC(C)C)[n:17]2)[cH:16]c1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([C:11]([F:12])([F:13])[F:14])[cH:15][cH:16]2)[n:17][nH:18][c:19]... | CCOC(=O)C(O)(CC(=O)c1ccc(C(F)(F)F)cc1)C(=O)OCC.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1 | O=C(O)c1cc(-c2ccc(C(F)(F)F)cc2)n[nH]c1=O | null | null | null | Functional Group Interconversion | OtherReaction | 2bc8b1e0e0e579c980271e96c3fa66a1c31cc20cd4249ce20d59dc79a05fa188 | 8b081616cd9412d60acf395024d8add918d2568e22665faf331488bdf21c247d | O=c1ccc(-c2ccccc2)n[nH]1 | C-C(-C)-C-[n;H0;D3;+0:1]1:[#7;a:2]:[c:3](-[c;H0;D3;+0:4]2:[cH;D2;+0:5]:c:c(-C):c:c:2):[c:6]:[c:7](-[CH2;D2;+0:8]-[O;H0;D2;+0:9]-S(-C)(=O)=O):[c:10]:1=[O;D1;H0:11].C-C-O-C(=O)-C(-O)(-C-C(=O)-c1:[cH;D2;+0:12]:[c:13]:[c:14](-[C:15](-[F;D1;H0:16])(-[F;D1;H0:17])-[F;D1;H0:18]):[cH;D2;+0:19]:c:1)-C(=[O;H0;D1;+0:20])-O-C-C>>[... | 91.4 | [{"value": 91.4, "product": "C(=O)(O)C=1C(NN=C(C1)C1=CC=C(C=C1)C(F)(F)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (4), ethyl 2-ethoxycarbonyl-2-hydroxy-4-(4-trifluoromethylphenyl)-4-oxobutanoate was reacted to yield the title compound as a pale brown crystalline powder (yield: 91.4%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Ketone.Ester.Ester.Tertiary alcohol | Carboxylic acid | c1ccccc1.c1ccccc1.c1ccnnc1 | c1cnncc1.c1ccccc1 | c1cnncc1.c1ccccc1 | MsOH.HO- | null | null | null | CCOC(=O)C(O)(CC(=O)c1ccc(C(F)(F)F)cc1)C(=O)OCC.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1>>O=C(O)c1cc(-c2ccc(C(F)(F)F)cc2)n[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b6623aafc3be420190abc80d4c625a60 | Cc1ccc(-c2cc(CN3CCN(Cc4ccccc4)CC3)c(=O)n(CC(C)C)n2)cc1.O=C(O)c1cc(-c2ccc(C(F)(F)F)cc2)n[nH]c1=O>>COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)n[nH]c1=O | C(C1=CC=CC=C1)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC=C(C=C1)C)CC(C)C)=O.C(=O)(O)C=1C(NN=C(C1)C1=CC=C(C=C1)C(F)(F)F)=O>>COC(=O)C=1C(NN=C(C1)C1=CC=C(C=C1)C(F)(F)F)=O | CC(C)Cn1nc(-c2ccc([CH3:1])cc2)cc(CN2CCN(Cc3ccccc3)CC2)c1=O.[OH:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[n:18][nH:19][c:20]1=[O:21]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[n:18][n... | Cc1ccc(-c2cc(CN3CCN(Cc4ccccc4)CC3)c(=O)n(CC(C)C)n2)cc1.O=C(O)c1cc(-c2ccc(C(F)(F)F)cc2)n[nH]c1=O | COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)n[nH]c1=O | null | null | null | Heteroatom Alkylation and Arylation | O-methylation | 7470a92d419372ae15476362de0368a0d4152b4c2de21b9efbea3527d0439d84 | 39f021a6948288c2dbafd234a73d5e01999ac4edfc19989e75fdd1caade55c07 | O=c1ccc(-c2ccccc2)n[nH]1 | C-C(-C)-C-n1:n:c(-c2:c:c:c(-[CH3;D1;+0:1]):c:c:2):c:c(-C-N2-C-C-N(-C-c3:c:c:c:c:c:3)-C-C-2):c:1=O.[#7;a:2]:[c:3]:[c:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[#7;a:2]:[c:3]:[c:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH3;D1;+0:1] | 88.5 | [{"value": 88.5, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (5), 4-carboxy-6-(4-trifluoromethylphenyl)-2H-pyridazin-3-one was reacted to yield the title compound as slightly yellow crystalline powder (yield: 88.5%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Tertiary amine.Tertiary amine | Ester | c1ccnnc1.c1ccccc1.C1CNCCN1.c1ccccc1 | null | c1cnncc1.c1ccccc1 | HO- | null | null | null | Cc1ccc(-c2cc(CN3CCN(Cc4ccccc4)CC3)c(=O)n(CC(C)C)n2)cc1.O=C(O)c1cc(-c2ccc(C(F)(F)F)cc2)n[nH]c1=O>>COC(=O)c1cc(-c2ccc(C(F)(F)F)cc2)n[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-38f54bda284b4a1c97d183b361a15695 | CC(C)Cn1nc(-c2ccc(C(F)(F)F)cc2)cc(C(=O)O)c1=O>>CC(C)Cn1nc(-c2ccc(C(F)(F)F)cc2)cc(CO)c1=O | FC=1C=C(C=CC1C)C=1C(=C(C(N(N1)CC(C)C)=O)O)C.C(=O)(O)C=1C(N(N=C(C1)C1=CC=C(C=C1)C(F)(F)F)CC(C)C)=O>>OCC=1C(N(N=C(C1)C1=CC=C(C=C1)C(F)(F)F)CC(C)C)=O | O=[C:20]([c:19]1[cH:18][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:22]1=[O:23])[OH:21]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:18][c:19]([CH2:20][OH:21])[c:22]... | CC(C)Cn1nc(-c2ccc(C(F)(F)F)cc2)cc(C(=O)O)c1=O | CC(C)Cn1nc(-c2ccc(C(F)(F)F)cc2)cc(CO)c1=O | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)n[nH]1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10]>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:9]:1=[O;D1;H0:10] | 28.1 | [{"value": 28.1, "product": "OCC=1C(N(N=C(C1)C1=CC=C(C=C1)C(F)(F)F)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-carboxy-2-isobutyl-6-(4-trifluoromethylphenyl)-2H-pyridazin-3-one was reacted to yield the title compound as colorless fine-needles (yield: 28.1%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccnnc1.c1ccccc1 | Other | null | null | null | CC(C)Cn1nc(-c2ccc(C(F)(F)F)cc2)cc(C(=O)O)c1=O>>CC(C)Cn1nc(-c2ccc(C(F)(F)F)cc2)cc(CO)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b6ddb63eb53b46ee8d6f1449f5c6896e | Cc1c(-c2ccc(C(F)(F)F)cc2)nn(CC(C)C)c(=O)c1O.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F>>CC(C)Cn1nc(-c2ccc(C(F)(F)F)cc2)cc(COS(C)(=O)=O)c1=O | FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.OC=1C(N(N=C(C1C)C1=CC=C(C=C1)C(F)(F)F)CC(C)C)=O>>C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)C(F)(F)F | Cc1c(-c2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)nn(CC(C)C)c(=O)c1O.Cc1cc[c:8](-[c:7]2[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:26](=[O:27])[c:19]([CH2:20][O:21][S:22]([CH3:23])(=[O:24])=[O:25])[cH:18]2)cc1F>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13... | Cc1c(-c2ccc(C(F)(F)F)cc2)nn(CC(C)C)c(=O)c1O.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F | CC(C)Cn1nc(-c2ccc(C(F)(F)F)cc2)cc(COS(C)(=O)=O)c1=O | null | null | null | Miscellaneous | OtherReaction | bd719d0b7487767de39b80bd2b00d22d0935945067d57ed5356831cec138b379 | ac57deee2f15607d8f9e1dd7c4901e07da2c0ef1e4c35658286d8e27f40d53c0 | O=c1ccc(-c2ccccc2)n[nH]1 | C-C(-C)-C-n1:n:c(-c2:[cH;D2;+0:1]:[c:2]:[c:3]:[c:4]:[cH;D2;+0:5]:2):c(-C):c(-O):c:1=O.C-c1:c:c:[c;H0;D3;+0:6](-[c:7](:[c:8]):[#7;a:9]:[#7;a:10](-[C:11]):[c:12]):c:c:1-F>>[C:11]-[#7;a:10](:[c:12]):[#7;a:9]:[c:7](-[c;H0;D3;+0:6]1:[cH;D2;+0:1]:[c:2]:[c:3]:[c:4]:[cH;D2;+0:5]:1):[c:8] | 89.9 | [{"value": 89.9, "product": "C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (9), 4-hydroxy-methyl-2-isobutyl-6-(4-trifluoromethylphenyl)-2H-pyridazin-3-one was reacted to yield the title compound as colorless fine-needles (yield: 89.9%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic alcohol | null | c1ccnnc1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccnnc1.c1ccccc1 | HF | null | null | null | Cc1c(-c2ccc(C(F)(F)F)cc2)nn(CC(C)C)c(=O)c1O.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F>>CC(C)Cn1nc(-c2ccc(C(F)(F)F)cc2)cc(COS(C)(=O)=O)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c1f46b23e6e743a4b919e7d1516313c3 | CC(C)(C)OC(=O)N1CCNCC1.CC(C)Cn1nc(-c2ccc(C(F)(F)F)cc2)cc(COS(C)(=O)=O)c1=O.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1c(-c2ccc(C(F)(F)F)cc2)nn(CC(C)C)c(=O)c1N1CCN(C(=O)OC(C)(C)C)CC1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)C(F)(F)F.N1(CCNCC1)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC=C(C=C1)C(F)(F)F)CC(C)C)=O | [NH:23]1[CH2:24][CH2:25][N:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34][CH2:35]1.CS(=O)(=O)OC[c:22]1[cH:2][c:3](-[c:4]2[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][cH:13]2)[n:14][n:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[c:20]1=[O:21].Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2... | CC(C)(C)OC(=O)N1CCNCC1.CC(C)Cn1nc(-c2ccc(C(F)(F)F)cc2)cc(COS(C)(=O)=O)c1=O.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F | Cc1c(-c2ccc(C(F)(F)F)cc2)nn(CC(C)C)c(=O)c1N1CCN(C(=O)OC(C)(C)C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2a0dbc48e846de8e0c36eabe2ecaa3dda67e2c62a942dd827dcb6cda2589c033 | f8979a7dc32618975f84bf1d08d0eb1a0766a30fc7e3bcdfee8ffc6d86d4188b | O=c1[nH]nc(-c2ccccc2)cc1N1CCNCC1 | C-C(-C)-C-n1:n:c(-c2:c:c:c(-C):c(-F):c:2):c(-[CH3;D1;+0:1]):c(-N2-C-C-N(-C(=O)-O-C(-C)(-C)-C)-C-C-2):c:1=O.C-S(=O)(=O)-O-C-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c:4](-[c:5]):[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:4](-[c:5]):[c;H0;D3;+0:3]... | 83.5 | [{"value": 83.5, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC=C(C=C1)C(F)(F)F)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-isobutyl-4-methanesulfonyloxymethyl-6-(4-trifluoromethylphenyl)-2H-pyridazin-3-one and tert-butyl 1-piperazinecarboxylate were reacted to yield the title compound as a yellow oil (yield: 83.5%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic halide.Carbamic ester.Ether.Secondary amine.Tertiary amine.Boc | Tertiary amine | C1CNCC[NH]1.c1ccnnc1.c1ccccc1.c1ccnnc1.C1CNCCN1 | c1ccnnc1.C1C[NH]CC[NH]1 | c1ccnnc1.c1ccccc1.C1C[NH]CC[NH]1 | MsOH.HF | null | null | null | CC(C)(C)OC(=O)N1CCNCC1.CC(C)Cn1nc(-c2ccc(C(F)(F)F)cc2)cc(COS(C)(=O)=O)c1=O.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1c(-c2ccc(C(F)(F)F)cc2)nn(CC(C)C)c(=O)c1N1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-335249b52a204b2e9d7f05e2d6baf82d | CC(C)Cn1nc(-c2ccc(C(F)(F)F)cc2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1c(-c2ccc(C(F)(F)F)cc2)nn(CC(C)C)c(=O)c1N1CCN(C)CC1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)C(F)(F)F.CN1CCNCC1>>C(C(C)C)N1N=C(C(=C(C1=O)N1CCN(CC1)C)C)C1=CC=C(C=C1)C(F)(F)F | CS(=O)(=O)OC[c:22]1[cH:2][c:3](-[c:4]2[cH:5][cH:6][c:7]([C:8]([F:9])([F:10])[F:11])[cH:12][cH:13]2)[n:14][n:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[c:20]1=[O:21].[NH:23]1[CH2:24][CH2:25][N:26]([CH3:27])[CH2:28][CH2:29]1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2[CH3:1])cc1F>>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][... | CC(C)Cn1nc(-c2ccc(C(F)(F)F)cc2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F | Cc1c(-c2ccc(C(F)(F)F)cc2)nn(CC(C)C)c(=O)c1N1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2a0dbc48e846de8e0c36eabe2ecaa3dda67e2c62a942dd827dcb6cda2589c033 | f8979a7dc32618975f84bf1d08d0eb1a0766a30fc7e3bcdfee8ffc6d86d4188b | O=c1[nH]nc(-c2ccccc2)cc1N1CCNCC1 | C-C(-C)-C-n1:n:c(-c2:c:c:c(-C):c(-F):c:2):c(-[CH3;D1;+0:1]):c(-N2-C-C-N(-C(=O)-O-C(-C)(-C)-C)-C-C-2):c:1=O.C-S(=O)(=O)-O-C-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c:4](-[c:5]):[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:4](-[c:5]):[c;H0;D3;+0:3]... | 81.1 | [{"value": 81.1, "product": "C(C(C)C)N1N=C(C(=C(C1=O)N1CCN(CC1)C)C)C1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-isobutyl-4-methanesulfonyloxymethyl-6-(4-trifluoromethylphenyl)-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 81.1%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic halide.Carbamic ester.Ether.Secondary amine.Tertiary amine.Boc | Tertiary amine | c1ccnnc1.C1CNCC[NH]1.c1ccccc1.c1ccnnc1.C1CNCCN1 | c1ccnnc1.C1C[NH]CC[NH]1 | c1ccnnc1.c1ccccc1.C1C[NH]CC[NH]1 | MsOH.HF | null | null | null | CC(C)Cn1nc(-c2ccc(C(F)(F)F)cc2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1c(-c2ccc(C(F)(F)F)cc2)nn(CC(C)C)c(=O)c1N1CCN(C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5547f5b907224c35ac7a447e8c6a6065 | COC(=O)c1cc(-c2ccc(-c3ccccc3)cc2)nn(CC(C)C)c1=O>>CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(C(=O)O)c1=O | C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)C(F)(F)F.C1(=CC=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)OC)C1=CC=CC=C1>>C1(=CC=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)O)C1=CC=CC=C1 | C[O:24][C:22]([c:21]1[cH:20][c:7](-[c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19]2)[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:25]1=[O:26])=[O:23]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19]2... | COC(=O)c1cc(-c2ccc(-c3ccccc3)cc2)nn(CC(C)C)c1=O | CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(C(=O)O)c1=O | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccc(-c3ccccc3)cc2)n[nH]1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 79.2 | [{"value": 79.2, "product": "C1(=CC=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)O)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (7), 6-(4-biphenylyl)-2-isobutyl-4-methoxycarbonyl-2H-pyridazin-3-one was reacted to yield the title compound as a colorless crystalline powder (yield: 79.2%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccnnc1.c1ccccc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(-c2ccc(-c3ccccc3)cc2)nn(CC(C)C)c1=O>>CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(C(=O)O)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f8f54937e925455ca895367bff749d2c | CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(C(=O)O)c1=O>>CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(CO)c1=O | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC=C(C=C1)C(F)(F)F)CC(C)C)=O.C1(=CC=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)O)C1=CC=CC=C1>>C1(=CC=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)CO)C1=CC=CC=C1 | O=[C:22]([c:21]1[cH:20][c:7](-[c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19]2)[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:24]1=[O:25])[OH:23]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19]2)[cH:... | CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(C(=O)O)c1=O | CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(CO)c1=O | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccc(-c3ccccc3)cc2)n[nH]1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10]>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:9]:1=[O;D1;H0:10] | 15.6 | [{"value": 15.6, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 6-(4-biphenylyl)-4-carboxy-2-isobutyl-2H-pyridazin-3-one was reacted to yield the title compound as a while solid (yield: 15.6%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccnnc1.c1ccccc1.c1ccccc1 | Other | null | null | null | CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(C(=O)O)c1=O>>CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(CO)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c9f6ceb80a5a4bf7a99591e44b771470 | CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1>>CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(CN2CCN(C)CC2)c1=O | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C1(=CC=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C)C1=CC=CC=C1.CN1CCNCC1>>C1(=CC=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCN(CC1)C)C1=CC=CC=C1 | CS(=O)(=O)O[CH2:22][c:21]1[cH:20][c:7](-[c:8]2[cH:9][cH:10][c:11](-[c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[cH:18][cH:19]2)[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:30]1=[O:31].[NH:23]1[CH2:24][CH2:25][N:26]([CH3:27])[CH2:28][CH2:29]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11](-[c:1... | CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1 | CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(CN2CCN(C)CC2)c1=O | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1[nH]nc(-c2ccc(-c3ccccc3)cc2)cc1CN1CCNCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 68.2 | [{"value": 68.2, "product": "C1(=CC=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCN(CC1)C)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 6-(4-biphenylyl)-2-isobutyl-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 68.2%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccnnc1.c1ccccc1.c1ccccc1.C1C[NH]CC[NH]1 | MsOH.HO- | null | null | null | CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1>>CC(C)Cn1nc(-c2ccc(-c3ccccc3)cc2)cc(CN2CCN(C)CC2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-faca1f7aeacd4eaa836f2f19d268303f | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2nn(CC(C)C)c(=O)c(OS(C)(=O)=O)c2C)cc1Cl>>COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC(C)C)n2)cc1Cl | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.ClC=1C=C(C=CC1OC)C=1C(=C(C(N(N1)CC(C)C)=O)OS(=O)(=O)C)C.N1(CCNCC1)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)Cl)CC(C)C)=O | [NH:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]1.CS(=O)(=O)O[c:9]1[c:8]([CH3:10])[c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:33]([Cl:34])[cH:32]2)[n:31][n:26]([CH2:27][CH:28]([CH3:29])[CH3:30])[c:24]1=[O:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:... | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2nn(CC(C)C)c(=O)c(OS(C)(=O)=O)c2C)cc1Cl | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC(C)C)n2)cc1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 20463218c281e2c61bf0173d651b213ee8033fd2ccbdfc94848e31db5e0e51b8 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1[nH]nc(-c2ccccc2)cc1CN1CCNCC1 | C-S(=O)(=O)-O-[c;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[#7;a:4](-[C:5]):[#7;a:6]:[c:7](-[c:8]):[c;H0;D3;+0:9]:1-[CH3;D1;+0:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[C:5]-[#7;a:4]1:[#7;a:6]:[c:7](-[c:8]):[cH;D2;+0:9]:[c;H0;D3;+0:1](-[CH2;D2;+0:10]-[N;H0;D3;+0:14]2-[C:13]-[C:12]-[#7:11]-[C:16]-[C:15]-2):[c:2]... | 89 | [{"value": 89.0, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)Cl)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 6-(3-chloro-4-methoxyphenyl)-2-isobutyl-4-methanesulfonyloxy-methyl-2H-pyridazin-3-one and tert-butyl 1-piperazine-carboxylate were reacted to yield the title compound as a yellow oil (yield: 89.0%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccnnc1 | c1ccnnc1.C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1 | MsOH.HO- | null | null | null | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2nn(CC(C)C)c(=O)c(OS(C)(=O)=O)c2C)cc1Cl>>COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC(C)C)n2)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-26c73ad3ae4b41328c85d2d897962363 | CN1CCNCC1.COc1ccc(-c2nn(CC(C)C)c(=O)c(OS(C)(=O)=O)c2C)cc1Cl>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC(C)C)n2)cc1Cl | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.ClC=1C=C(C=CC1OC)C=1C(=C(C(N(N1)CC(C)C)=O)OS(=O)(=O)C)C.CN1CCNCC1>>ClC=1C=C(C=CC1OC)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCN(CC1)C | [NH:11]1[CH2:12][CH2:13][N:14]([CH3:15])[CH2:16][CH2:17]1.CS(=O)(=O)O[c:9]1[c:8]([CH3:10])[c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:27]([Cl:28])[cH:26]2)[n:25][n:20]([CH2:21][CH:22]([CH3:23])[CH3:24])[c:18]1=[O:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][N:11]3[CH2:12][CH2:13][N:14]([CH3:1... | CN1CCNCC1.COc1ccc(-c2nn(CC(C)C)c(=O)c(OS(C)(=O)=O)c2C)cc1Cl | COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC(C)C)n2)cc1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 20463218c281e2c61bf0173d651b213ee8033fd2ccbdfc94848e31db5e0e51b8 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1[nH]nc(-c2ccccc2)cc1CN1CCNCC1 | C-S(=O)(=O)-O-[c;H0;D3;+0:1]1:[c:2](=[O;D1;H0:3]):[#7;a:4](-[C:5]):[#7;a:6]:[c:7](-[c:8]):[c;H0;D3;+0:9]:1-[CH3;D1;+0:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[C:5]-[#7;a:4]1:[#7;a:6]:[c:7](-[c:8]):[cH;D2;+0:9]:[c;H0;D3;+0:1](-[CH2;D2;+0:10]-[N;H0;D3;+0:14]2-[C:13]-[C:12]-[#7:11]-[C:16]-[C:15]-2):[c:2]... | 76.1 | [{"value": 76.1, "product": "ClC=1C=C(C=CC1OC)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 6-(3-chloro-4-methoxyphenyl)-2-isobutyl-4-methanesulfonyloxy-methyl-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 76.1%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1.c1ccnnc1 | c1ccnnc1.C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1 | MsOH.HO- | null | null | null | CN1CCNCC1.COc1ccc(-c2nn(CC(C)C)c(=O)c(OS(C)(=O)=O)c2C)cc1Cl>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC(C)C)n2)cc1Cl |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e384fbb2163e43f097684179ab1f7a1d | C1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)ccc1F>>Cc1cc(-c2cc(CN3CCCCC3)c(=O)n(CC(C)C)n2)ccc1F | FC1=C(C=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C)C.N1CCCCC1>>FC1=C(C=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCCCC1)C | [NH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1.CS(=O)(=O)O[CH2:8][c:7]1[cH:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:25]([F:26])[cH:24][cH:23]2)[n:22][n:17]([CH2:18][CH:19]([CH3:20])[CH3:21])[c:15]1=[O:16]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([CH2:8][N:9]3[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]3)[c:15](=[O:16])[... | C1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)ccc1F | Cc1cc(-c2cc(CN3CCCCC3)c(=O)n(CC(C)C)n2)ccc1F | null | null | C(C)O | Heteroatom Alkylation and Arylation | Alkylation of amines | d9333bb5e81b2a4e56015146d2514db60fc0485d8a32b9d10434a86ed081ca83 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1[nH]nc(-c2ccccc2)cc1CN1CCCCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C:14]>>[C:10]-[C:11]-[N;H0;D3;+0:12](-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9])-[C:13]-[C:14] | 94 | [{"value": 94.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | 6-(4-Fluoro-3-methylphenyl)-2-isobutyl-4-methane-sulfonyloxymethyl-2H-pyridazin-3-one (80 mg, 0.22 mmol) and piperidine (55 mg, 0.65 mmol) were dissolved in ethanol (0.5 mL), and the mixture was heated at 80° C. for 1 hour under stirring. The solvent was distilled off. The residue was purified by preparative thin-layer... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccnnc1.C1CC[NH]CC1 | MsOH.HO- | C(C)O | 80 | null | C1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)ccc1F>C(C)O>Cc1cc(-c2cc(CN3CCCCC3)c(=O)n(CC(C)C)n2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d2dc42ea7cb747d5bda9b902f7363743 | C1COCCN1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)ccc1F>>Cc1cc(-c2cc(CN3CCOCC3)c(=O)n(CC(C)C)n2)ccc1F | FC1=C(C=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C)C.N1CCOCC1>>FC1=C(C=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCOCC1)C | [NH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1.CS(=O)(=O)O[CH2:8][c:7]1[cH:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:25]([F:26])[cH:24][cH:23]2)[n:22][n:17]([CH2:18][CH:19]([CH3:20])[CH3:21])[c:15]1=[O:16]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([CH2:8][N:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)[c:15](=[O:16])[n:17... | C1COCCN1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)ccc1F | Cc1cc(-c2cc(CN3CCOCC3)c(=O)n(CC(C)C)n2)ccc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | d65566d5f2049ef4dc70d5c480ea5af77518b25af8327af37e9d6d45c6baf558 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1[nH]nc(-c2ccccc2)cc1CN1CCOCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#8:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#8:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 97.4 | [{"value": 97.4, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 92, 6-(4-fluoro-3-methylphenyl)-2-isobutyl-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and morpholine were reacted to yield the title compound as a slightly yellow oil (yield: 97.4%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1COCCN1 | C1COCC[NH]1 | c1ccccc1.c1ccnnc1.C1COCC[NH]1 | MsOH.HO- | null | null | null | C1COCCN1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)ccc1F>>Cc1cc(-c2cc(CN3CCOCC3)c(=O)n(CC(C)C)n2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-831c0701f36045b3a8991ed9bcbd88f9 | CCNCC.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)ccc1F>>CCN(CC)Cc1cc(-c2ccc(F)c(C)c2)nn(CC(C)C)c1=O | C(C)NCC.FC1=C(C=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)OC)C.FC1=C(C=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C)C>>C(C)N(CC)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)F)C)CC(C)C)=O | [CH3:1][CH2:2][NH:3][CH2:4][CH3:5].CS(=O)(=O)O[CH2:6][c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([F:14])[c:15]([CH3:16])[cH:17]2)[n:18][n:19]([CH2:20][CH:21]([CH3:22])[CH3:23])[c:24]1=[O:25]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([F:14])[c:15]([CH3:16])[cH:17]2)[n:1... | CCNCC.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)ccc1F | CCN(CC)Cc1cc(-c2ccc(F)c(C)c2)nn(CC(C)C)c1=O | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1ccc(-c2ccccc2)n[nH]1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C;D1;H3:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C;D1;H3:14]>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:12](-[C:11]-[C;D1;H3:10])-[C:13]-[C;D1;H3:14]):[c:8]:1=[O;D1;H0:9] | 94.7 | [{"value": 94.7, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 9 (4), 6-(4-fluoro-3-methylphenyl)-2-isobutyl-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and diethylamine were reacted to yield the title compound as a slightly yellow oil (yield: 94.7%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccnnc1.c1ccccc1 | MsOH.HO- | null | null | null | CCNCC.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)ccc1F>>CCN(CC)Cc1cc(-c2ccc(F)c(C)c2)nn(CC(C)C)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c8bc44c09c944120ae7f421e56636c18 | CCOC(=O)C(O)(CC(=O)c1ccc(F)c(F)c1)C(=O)OCC.COC(=O)c1cc(-c2ccc(F)c(C)c2)nn(CC(C)C)c1=O>>O=C(O)c1cc(-c2ccc(F)c(F)c2)n[nH]c1=O | FC1=C(C=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)OC)C.FC=1C=C(C=CC1F)C(CC(C(=O)OCC)(O)C(=O)OCC)=O>>C(=O)(O)C=1C(NN=C(C1)C1=CC(=C(C=C1)F)F)=O | CCOC(=O)C(O)(CC(=O)c1ccc(F)c([F:13])c1)C(=O)OCC.CC(C)C[n:16]1[n:15][c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[c:12](C)[cH:14]2)[cH:5][c:4]([C:2](=[O:1])[O:3]C)[c:17]1=[O:18]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[c:12]([F:13])[cH:14]2)[n:15][nH:16][c:17]1=[O:18] | CCOC(=O)C(O)(CC(=O)c1ccc(F)c(F)c1)C(=O)OCC.COC(=O)c1cc(-c2ccc(F)c(C)c2)nn(CC(C)C)c1=O | O=C(O)c1cc(-c2ccc(F)c(F)c2)n[nH]c1=O | null | null | null | Functional Group Interconversion | OtherReaction | e0293bfe69e1f2bb181ca9141fc6790468a9ea80d6a87c36c317bfc88c05573b | 79122415426c24d372cb99f0723f4769d68485992167f56cc179db344c46cc43 | O=c1ccc(-c2ccccc2)n[nH]1 | C-C-O-C(=O)-C(-O)(-C-C(=O)-c1:c:c:c(-F):c(-[F;H0;D1;+0:1]):c:1)-C(=O)-O-C-C.C-[O;H0;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](=[O;D1;H0:7]):[n;H0;D3;+0:8](-C-C(-C)-C):[#7;a:9]:[c:10]-[c:11]:[c:12]:[c;H0;D3;+0:13](-C):[c:14](-[F;D1;H0:15]):[c:16]>>[F;D1;H0:15]-[c:14](:[c:16]):[c;H0;D3;+0:13](-[F;H0;D1;+0:1]):[c:12]:[c:11... | 88.9 | [{"value": 88.9, "product": "C(=O)(O)C=1C(NN=C(C1)C1=CC(=C(C=C1)F)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (4), ethyl 4-(3,4-difluorophenyl)-2-ethoxycarbonyl-2-hydroxy-4-oxo-butanoate was reacted to yield the title compound as a pale yellow crystalline powder (yield: 88.9%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ketone.Ester.Ester.Ester.Tertiary alcohol | Aromatic halide.Carboxylic acid | c1ccccc1.c1ccnnc1.c1ccccc1 | c1cnncc1.c1ccccc1 | c1cnncc1.c1ccccc1 | HF | null | null | null | CCOC(=O)C(O)(CC(=O)c1ccc(F)c(F)c1)C(=O)OCC.COC(=O)c1cc(-c2ccc(F)c(C)c2)nn(CC(C)C)c1=O>>O=C(O)c1cc(-c2ccc(F)c(F)c2)n[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-af73b051fe144fdba335731eb1906f61 | COC(=O)c1cc(-c2ccc(F)c(F)c2)n[nH]c1=O.Cc1cc(-c2nn(CC(C)C)c(=O)c(O)c2C)ccc1F>>COC(=O)c1cc(-c2ccc(F)c(F)c2)nn(CC(C)C)c1=O | FC1=C(C=C(C=C1)C=1C(=C(C(N(N1)CC(C)C)=O)O)C)C.FC=1C=C(C=CC1F)C=1C=C(C(NN1)=O)C(=O)OC>>FC=1C=C(C=CC1F)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)OC | Fc1ccc(-c2n[nH][c:22](=[O:23])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6]2)cc1[F:14].Cc1c(O)c(=O)[n:17]([CH2:18][CH:19]([CH3:20])[CH3:21])[n:16][c:7]1-[c:8]1[cH:9][cH:10][c:11]([F:12])[c:13](C)[cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[cH:15]2)[n:16][n:17]([CH2:18][... | COC(=O)c1cc(-c2ccc(F)c(F)c2)n[nH]c1=O.Cc1cc(-c2nn(CC(C)C)c(=O)c(O)c2C)ccc1F | COC(=O)c1cc(-c2ccc(F)c(F)c2)nn(CC(C)C)c1=O | null | null | null | Functional Group Interconversion | OtherReaction | 4a36575d9047b24caff14070eeff6afadbe3f37a7dcca4412ede05b7517544c3 | c557fa819935823cc7793443b7c2e2d377dfed9e9db18a7af4cddb6379a99d41 | O=c1ccc(-c2ccccc2)n[nH]1 | C-[c;H0;D3;+0:1]1:[c:2]:[c:3](-[c;H0;D3;+0:4]2:[#7;a:5]:[n;H0;D3;+0:6](-[C:7]-[C:8]):c(=O):c(-O):c:2-C):[c:9]:[c:10]:[c:11]:1-[F;D1;H0:12].F-c1:c:c:c(-c2:[cH;D2;+0:13]:[c:14](-[C:15](=[O;D1;H0:16])-[#8:17]-[C;D1;H3:18]):[c;H0;D3;+0:19](=[O;D1;H0:20]):[nH]:n:2):c:c:1-[F;H0;D1;+0:21]>>[C:8]-[C:7]-[n;H0;D3;+0:6]1:[#7;a:5]... | null | [] | null | null | null | null | Following the procedure of Example 1 (6), 6-(3,4-difluorophenyl)-4-methoxycarbonyl-2H-pyridazin-3-one was reacted to yield the title compound as a yellow oil (yield: quantitative).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Aromatic alcohol | Aromatic halide | c1ccccc1.c1cnncc1.c1ccnnc1.c1ccccc1 | c1ccnnc1.c1ccccc1 | c1ccnnc1.c1ccccc1 | HF | null | null | null | COC(=O)c1cc(-c2ccc(F)c(F)c2)n[nH]c1=O.Cc1cc(-c2nn(CC(C)C)c(=O)c(O)c2C)ccc1F>>COC(=O)c1cc(-c2ccc(F)c(F)c2)nn(CC(C)C)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-714bb13112614b41842047c2a94caf55 | COC(=O)c1cc(-c2ccc(F)c(F)c2)nn(CC(C)C)c1=O>>CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(C(=O)O)c1=O | FC1=C(C=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C)C.FC=1C=C(C=CC1F)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)OC>>C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)F)F)CC(C)C)=O | C[O:20][C:18]([c:17]1[cH:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[cH:15]2)[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:21]1=[O:22])=[O:19]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[cH:15]2)[cH:16][c:17]([C:18](=[O:19])[OH:20])[c:21]1=[O:22] | COC(=O)c1cc(-c2ccc(F)c(F)c2)nn(CC(C)C)c1=O | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(C(=O)O)c1=O | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccccc2)n[nH]1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 91.4 | [{"value": 91.4, "product": "C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)F)F)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (7), 6-(3,4-difluorophenyl)-2-isobutyl-4-methoxycarbonyl-2H-pyridazin-3-one was reacted to yield the title compound as colorless fine needles (yield: 91.4%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccnnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(-c2ccc(F)c(F)c2)nn(CC(C)C)c1=O>>CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(C(=O)O)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fdde27bcafa44772a696d31f27493e13 | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(C(=O)O)c1=O>>CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(CO)c1=O | FC1=C(C=C(C=C1)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCN(CC1)C)C.C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)F)F)CC(C)C)=O>>FC=1C=C(C=CC1F)C=1C=C(C(N(N1)CC(C)C)=O)CO | O=[C:18]([c:17]1[cH:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[cH:15]2)[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:20]1=[O:21])[OH:19]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[cH:15]2)[cH:16][c:17]([CH2:18][OH:19])[c:20]1=[O:21] | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(C(=O)O)c1=O | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(CO)c1=O | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)n[nH]1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10]>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:9]:1=[O;D1;H0:10] | 25 | [{"value": 25.0, "product": "FC=1C=C(C=CC1F)C=1C=C(C(N(N1)CC(C)C)=O)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-carboxy-6-(3,4-difluorophenyl)-2-isobutyl-2H-pyridazin-3-one was reacted to yield the title compound as colorless fine-needles (yield: 25.0%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccnnc1.c1ccccc1 | Other | null | null | null | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(C(=O)O)c1=O>>CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(CO)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-44a0c0f88285404fb3b5edd818d8b15f | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(CO)c1=O.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F>>CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(COS(C)(=O)=O)c1=O | FC=1C=C(C=CC1C)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.FC=1C=C(C=CC1F)C=1C=C(C(N(N1)CC(C)C)=O)CO>>FC=1C=C(C=CC1F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C | CC(C)Cn1nc(-c2ccc([F:12])c(F)c2)cc(CO)c1=O.C[c:11]1[cH:10][cH:9][c:8](-[c:7]2[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:24](=[O:25])[c:17]([CH2:18][O:19][S:20]([CH3:21])(=[O:22])=[O:23])[cH:16]2)[cH:15][c:13]1[F:14]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[cH:15]2... | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(CO)c1=O.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(COS(C)(=O)=O)c1=O | null | null | null | Functional Group Interconversion | OtherReaction | 5835f09e6840e88e6db9a41014734e89eaee069096c177289d60d597ee435c03 | 56e659f47d9252b007f813b09a15f03d832eb638a85e85c168d3aa25a7cb5ba1 | O=c1ccc(-c2ccccc2)n[nH]1 | C-C(-C)-C-n1:n:c(-c2:c:c:c(-[F;H0;D1;+0:1]):c(-F):c:2):c:c(-C-O):c:1=O.C-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5](-[F;D1;H0:6]):[c:7]>>[F;D1;H0:6]-[c:5](:[c:7]):[c;H0;D3;+0:2](-[F;H0;D1;+0:1]):[c:3]:[c:4] | 81.4 | [{"value": 81.4, "product": "FC=1C=C(C=CC1F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (9), 6-(3,4-difluorophenyl)-4-hydroxymethyl-2-isobutyl-2H-pyridazin-3-one was reacted to yield the title compound as colorless fine-needles (yield: 81.4%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Primary alcohol | Aromatic halide | c1ccnnc1.c1ccccc1.c1ccccc1 | c1ccccc1 | c1ccnnc1.c1ccccc1 | HF | null | null | null | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(CO)c1=O.Cc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1F>>CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(COS(C)(=O)=O)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ebb3484013254eb193e142fa189b745f | CC(C)(C)OC(=O)N1CCNCC1.CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(COS(C)(=O)=O)c1=O.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1c(-c2ccc(F)c(F)c2)nn(CC(C)C)c(=O)c1N1CCN(C(=O)OC(C)(C)C)CC1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.FC=1C=C(C=CC1F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.N1(CCNCC1)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)F)F)CC(C)C)=O | [NH:21]1[CH2:22][CH2:23][N:24]([C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32][CH2:33]1.CS(=O)(=O)OC[c:20]1[cH:2][c:3](-[c:4]2[cH:5][cH:6][c:7]([F:8])[c:9]([F:10])[cH:11]2)[n:12][n:13]([CH2:14][CH:15]([CH3:16])[CH3:17])[c:18]1=[O:19].Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2[CH3:1])cc1F>>[... | CC(C)(C)OC(=O)N1CCNCC1.CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(COS(C)(=O)=O)c1=O.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F | Cc1c(-c2ccc(F)c(F)c2)nn(CC(C)C)c(=O)c1N1CCN(C(=O)OC(C)(C)C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2a0dbc48e846de8e0c36eabe2ecaa3dda67e2c62a942dd827dcb6cda2589c033 | f8979a7dc32618975f84bf1d08d0eb1a0766a30fc7e3bcdfee8ffc6d86d4188b | O=c1[nH]nc(-c2ccccc2)cc1N1CCNCC1 | C-C(-C)-C-n1:n:c(-c2:c:c:c(-C):c(-F):c:2):c(-[CH3;D1;+0:1]):c(-N2-C-C-N(-C(=O)-O-C(-C)(-C)-C)-C-C-2):c:1=O.C-S(=O)(=O)-O-C-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c:4](-[c:5]):[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:4](-[c:5]):[c;H0;D3;+0:3]... | 85.5 | [{"value": 85.5, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)F)F)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 6-(3,4-difluorophenyl)-2-isobutyl-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and tert-butyl 1-piperazinecarboxylate were reacted to yield the title compound as a yellow oil (yield: 85.5%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic halide.Carbamic ester.Ether.Secondary amine.Tertiary amine.Boc | Tertiary amine | C1CNCC[NH]1.c1ccnnc1.c1ccccc1.c1ccnnc1.C1CNCCN1 | c1ccnnc1.C1C[NH]CC[NH]1 | c1ccnnc1.c1ccccc1.C1C[NH]CC[NH]1 | MsOH.HF | null | null | null | CC(C)(C)OC(=O)N1CCNCC1.CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(COS(C)(=O)=O)c1=O.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1c(-c2ccc(F)c(F)c2)nn(CC(C)C)c(=O)c1N1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f79b7d8fd2e84a7ab7b6864720a4cbf1 | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1>>CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(CN2CCN(C)CC2)c1=O | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.FC=1C=C(C=CC1F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.CN1CCNCC1>>FC=1C=C(C=CC1F)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCN(CC1)C | CS(=O)(=O)O[CH2:18][c:17]1[cH:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[cH:15]2)[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:26]1=[O:27].[NH:19]1[CH2:20][CH2:21][N:22]([CH3:23])[CH2:24][CH2:25]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[c:13]([F:14])[cH:15]2)[cH:16... | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1 | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(CN2CCN(C)CC2)c1=O | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1[nH]nc(-c2ccccc2)cc1CN1CCNCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 79.1 | [{"value": 79.1, "product": "FC=1C=C(C=CC1F)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 6-(3,4-difluorophenyl)-2-isobutyl-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 79.1%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccnnc1.c1ccccc1.C1C[NH]CC[NH]1 | MsOH.HO- | null | null | null | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1>>CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(CN2CCN(C)CC2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ee2345b762164753b9c1c18611bc97d5 | COC(=O)c1cc(-c2ccc(F)c(F)c2)nn(CC(C)C)c1=O>>O=C(O)c1cc(-c2ccc(F)cc2F)n[nH]c1=O | FC=1C=C(C=CC1F)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)OC.FC1=C(C=CC(=C1)F)C(CC(C(=O)OCC)(O)C(=O)OCC)=O>>C(=O)(O)C=1C(NN=C(C1)C1=C(C=C(C=C1)F)F)=O | CC(C)C[n:16]1[n:15][c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[c:12]([F:14])[cH:13]2)[cH:5][c:4]([C:2](=[O:1])[O:3]C)[c:17]1=[O:18]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][c:13]2[F:14])[n:15][nH:16][c:17]1=[O:18] | COC(=O)c1cc(-c2ccc(F)c(F)c2)nn(CC(C)C)c1=O | O=C(O)c1cc(-c2ccc(F)cc2F)n[nH]c1=O | null | null | null | Miscellaneous | OtherReaction | 5257c1bb35515249cb04ceaf41f60a6416644d4651f846684e58644a9ac1a255 | b7ac6870bdba6a67a6fd8cef6826e167071ad392928d9e1d015ed4c8194dfd49 | O=c1ccc(-c2ccccc2)n[nH]1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5](=[O;D1;H0:6]):[n;H0;D3;+0:7](-C-C(-C)-C):[#7;a:8]:[c:9]-[c:10]1:[c:11]:[c:12]:[c:13](-[F;D1;H0:14]):[c;H0;D3;+0:15](-[F;H0;D1;+0:16]):[cH;D2;+0:17]:1>>[F;D1;H0:14]-[c:13]1:[c:12]:[c:11]:[c:10](-[c:9]:[#7;a:8]:[nH;D2;+0:7]:[c:5](=[O;D1;H0:6]):[c:4]-[C:2](=[O;D1;H0:3])-[OH... | 95.2 | [{"value": 95.2, "product": "C(=O)(O)C=1C(NN=C(C1)C1=C(C=C(C=C1)F)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (4), ethyl 4-(2,4-difluorophenyl)-2-ethoxycarbonyl-2-hydroxy-4-oxo-butanoate was reacted to yield the title compound as a pale yellow crystalline powder (yield: 95.2%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ester | Aromatic halide.Carboxylic acid | c1ccnnc1.c1ccccc1 | c1cnncc1.c1ccccc1 | c1cnncc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(-c2ccc(F)c(F)c2)nn(CC(C)C)c1=O>>O=C(O)c1cc(-c2ccc(F)cc2F)n[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ae39ca789a344dbc8de31b5a25116b20 | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(C(=O)O)c1=O.O=C(O)c1cc(-c2ccc(F)cc2F)n[nH]c1=O>>COC(=O)c1cc(-c2ccc(F)cc2F)n[nH]c1=O | C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)F)F)CC(C)C)=O.C(=O)(O)C=1C(NN=C(C1)C1=C(C=C(C=C1)F)F)=O>>FC1=C(C=CC(=C1)F)C=1C=C(C(NN1)=O)C(=O)OC | CC(C)[CH2:1]n1nc(-c2ccc(F)c(F)c2)cc(C(=O)O)c1=O.[OH:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[n:16][nH:17][c:18]1=[O:19]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[n:16][nH:17][c:18]1=[O:19] | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(C(=O)O)c1=O.O=C(O)c1cc(-c2ccc(F)cc2F)n[nH]c1=O | COC(=O)c1cc(-c2ccc(F)cc2F)n[nH]c1=O | null | null | null | Heteroatom Alkylation and Arylation | O-methylation | efd3518bd4e279e7463f400044a98f4911803e5af738e85a6f10a9f54a28b709 | bac5ad78f1095a8bfffc9c2800911460b9010b919c5b879ef36013ff086ae4ac | O=c1ccc(-c2ccccc2)n[nH]1 | C-C(-C)-[CH2;D2;+0:1]-n1:n:c(-c2:c:c:c(-F):c(-F):c:2):c:c(-C(-O)=O):c:1=O.[#7;a:2]:[c:3]:[c:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7]>>[#7;a:2]:[c:3]:[c:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-[CH3;D1;+0:1] | 81.2 | [{"value": 81.2, "product": "FC1=C(C=CC(=C1)F)C=1C=C(C(NN1)=O)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (5), 4-carboxy-6-(2,4-difluorophenyl)-2H-pyridazin-3-one was reacted to yield the title compound as a pale yellow crystalline powder (yield: 81.2%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Carboxylic acid.Carboxylic acid | Ester | c1ccnnc1.c1ccccc1 | null | c1cnncc1.c1ccccc1 | HF | null | null | null | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(C(=O)O)c1=O.O=C(O)c1cc(-c2ccc(F)cc2F)n[nH]c1=O>>COC(=O)c1cc(-c2ccc(F)cc2F)n[nH]c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-da69e8aadcb04131b7b10677babb8669 | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(CO)c1=O.COC(=O)c1cc(-c2ccc(F)cc2F)n[nH]c1=O>>COC(=O)c1cc(-c2ccc(F)cc2F)nn(CC(C)C)c1=O | FC=1C=C(C=CC1F)C=1C=C(C(N(N1)CC(C)C)=O)CO.FC1=C(C=CC(=C1)F)C=1C=C(C(NN1)=O)C(=O)OC>>FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)OC | OCc1cc(-c2ccc(F)c(F)c2)n[n:17]([CH2:18][CH:19]([CH3:20])[CH3:21])[c:22]1=[O:23].O=c1[nH][n:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[cH:6][c:5]1[C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[n:16][n:17]([CH2:18][CH:19]... | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(CO)c1=O.COC(=O)c1cc(-c2ccc(F)cc2F)n[nH]c1=O | COC(=O)c1cc(-c2ccc(F)cc2F)nn(CC(C)C)c1=O | null | null | null | Miscellaneous | OtherReaction | dc0b9ec7a6bd8bc4e85eb7f1d4e63c4d90244e31d053bf2267795f44f51aafe6 | b34e6c48d7d9d20e631391e66183dcefeeabad220767b79e0a7d38df753371b4 | O=c1ccc(-c2ccccc2)n[nH]1 | F-c1:c:c:c(-c2:c:c(-C-O):[c;H0;D3;+0:1](=[O;D1;H0:2]):[n;H0;D3;+0:3](-[C:4]-[C:5]):n:2):c:c:1-F.O=c1:[nH]:[n;H0;D2;+0:6]:[c:7](-[c:8]):[c:9]:[c;H0;D3;+0:10]:1-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H3:14]>>[C:5]-[C:4]-[n;H0;D3;+0:3]1:[n;H0;D2;+0:6]:[c:7](-[c:8]):[c:9]:[c;H0;D3;+0:10](-[C:11](=[O;D1;H0:12])-[#8:13]-[C;D1;H... | 84.8 | [{"value": 84.8, "product": "FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (6), 6-(2,4-difluorophenyl)-4-methoxycarbonyl-2H-pyridazin-3-one was reacted to yield the title compound as a pale yellow oil (yield: 84.8%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aromatic halide.Ester.Primary alcohol | Ester | c1ccnnc1.c1ccccc1.c1ccnnc1 | c1ccnnc1 | c1ccnnc1.c1ccccc1 | HF | null | null | null | CC(C)Cn1nc(-c2ccc(F)c(F)c2)cc(CO)c1=O.COC(=O)c1cc(-c2ccc(F)cc2F)n[nH]c1=O>>COC(=O)c1cc(-c2ccc(F)cc2F)nn(CC(C)C)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-db2f469dbd3242369371d21ba7dc441a | COC(=O)c1cc(-c2ccc(F)cc2F)nn(CC(C)C)c1=O>>CC(C)Cn1nc(-c2ccc(F)cc2F)cc(C(=O)O)c1=O | FC=1C=C(C=CC1F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)OC>>C(=O)(O)C=1C(N(N=C(C1)C1=C(C=C(C=C1)F)F)CC(C)C)=O | C[O:20][C:18]([c:17]1[cH:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:21]1=[O:22])=[O:19]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[cH:16][c:17]([C:18](=[O:19])[OH:20])[c:21]1=[O:22] | COC(=O)c1cc(-c2ccc(F)cc2F)nn(CC(C)C)c1=O | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(C(=O)O)c1=O | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccccc2)n[nH]1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 92.7 | [{"value": 92.7, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (7), 6-(2,4-difluorophenyl)-2-isobutyl-4-methoxycarbonyl-2H-pyridazin-3-one was reacted to yield the title compound as slightly yellow needles (yield: 92.7%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccnnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(-c2ccc(F)cc2F)nn(CC(C)C)c1=O>>CC(C)Cn1nc(-c2ccc(F)cc2F)cc(C(=O)O)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-394277e0d63a4f63977661e2548de12b | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(C(=O)O)c1=O>>CC(C)Cn1nc(-c2ccc(F)cc2F)cc(CO)c1=O | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)F)F)CC(C)C)=O.C(=O)(O)C=1C(N(N=C(C1)C1=C(C=C(C=C1)F)F)CC(C)C)=O>>FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CO | O=[C:18]([c:17]1[cH:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:20]1=[O:21])[OH:19]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[cH:16][c:17]([CH2:18][OH:19])[c:20]1=[O:21] | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(C(=O)O)c1=O | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(CO)c1=O | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)n[nH]1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10]>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:9]:1=[O;D1;H0:10] | 45 | [{"value": 45.0, "product": "FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-carboxy-6-(2,4-difluorophenyl)-2-isobutyl-2H-pyridazin-3-one was reacted to yield the title compound as a pale yellow oil (yield: 45.0%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccnnc1.c1ccccc1 | Other | null | null | null | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(C(=O)O)c1=O>>CC(C)Cn1nc(-c2ccc(F)cc2F)cc(CO)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-1fcb1e8a1161461b9c33d7d322bdcc0b | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(CN2C(=O)c3ccccc3C2=O)c1=O>>CC(C)Cn1nc(-c2ccc(F)cc2F)cc(CN)c1=O | C(=O)(O)C=1C(NN=C(C1)C1=C(C=C(C=C1)F)F)=O.C(C(C)C)N1N=C(C=C(C1=O)CN1C(C=2C(C1=O)=CC=CC2)=O)C2=C(C=C(C=C2)F)F>>NCC=1C(N(N=C(C1)C1=C(C=C(C=C1)F)F)CC(C)C)=O | O=C1c2ccccc2C(=O)[N:19]1[CH2:18][c:17]1[cH:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:20]1=[O:21]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[cH:16][c:17]([CH2:18][NH2:19])[c:20]1=[O:21] | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(CN2C(=O)c3ccccc3C2=O)c1=O | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(CN)c1=O | null | null | null | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | O=c1ccc(-c2ccccc2)n[nH]1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[c:3]:[c:4]:[#7;a:5])-C(=O)-c2:c:c:c:c:c:2-1>>[#7;a:5]:[c:4]:[c:3]-[C:2]-[NH2;D1;+0:1] | 98.4 | [{"value": 98.4, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 24 (2), 2-isobutyl-6-(2,4-difluorophenyl)-4-phthalimidomethyl-2H-pyridazin-3-one was reacted to yield the title compound as a slightly yellow oil (yield: 98.4%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | c1ccnnc1.c1ccccc1 | HO- | null | null | null | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(CN2C(=O)c3ccccc3C2=O)c1=O>>CC(C)Cn1nc(-c2ccc(F)cc2F)cc(CN)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7f859e611fc340788dd94777d9e88e65 | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(COS(C)(=O)=O)c1=O.CCNCC>>CCN(CC)Cc1cc(-c2ccc(F)cc2F)nn(CC(C)C)c1=O | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)C(=O)OC.FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.C(C)NCC>>C(C)N(CC)CC=1C(N(N=C(C1)C1=C(C=C(C=C1)F)F)CC(C)C)=O | CS(=O)(=O)O[CH2:6][c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][c:16]2[F:17])[n:18][n:19]([CH2:20][CH:21]([CH3:22])[CH3:23])[c:24]1=[O:25].[CH3:1][CH2:2][NH:3][CH2:4][CH3:5]>>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([F:14])[cH:15][c:16]2[F:17])[n:18][n:19]... | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(COS(C)(=O)=O)c1=O.CCNCC | CCN(CC)Cc1cc(-c2ccc(F)cc2F)nn(CC(C)C)c1=O | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1ccc(-c2ccccc2)n[nH]1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C;D1;H3:10]-[C:11]-[NH;D2;+0:12]-[C:13]-[C;D1;H3:14]>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:12](-[C:11]-[C;D1;H3:10])-[C:13]-[C;D1;H3:14]):[c:8]:1=[O;D1;H0:9] | null | [] | null | null | null | null | Following the procedure of Example 9 (4), 6-(2,4-difluorophenyl)-2-isobutyl-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and diethylamine were reacted to yield the title compound as a pale yellow oil (yield: quantitative).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccnnc1.c1ccccc1 | MsOH.HO- | null | null | null | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(COS(C)(=O)=O)c1=O.CCNCC>>CCN(CC)Cc1cc(-c2ccc(F)cc2F)nn(CC(C)C)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d878a20ce6cb413cbe126b1d52df5605 | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1>>CC(C)Cn1nc(-c2ccc(F)cc2F)cc(CN2CCN(C)CC2)c1=O | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.CN1CCNCC1>>FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCN(CC1)C | CS(=O)(=O)O[CH2:18][c:17]1[cH:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:26]1=[O:27].[NH:19]1[CH2:20][CH2:21][N:22]([CH3:23])[CH2:24][CH2:25]1>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[cH:16][c:... | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1 | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(CN2CCN(C)CC2)c1=O | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1[nH]nc(-c2ccccc2)cc1CN1CCNCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 94 | [{"value": 94.0, "product": "FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CN1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 6-(2,4-difluorophenyl)-2-isobutyl-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a pale yellow oil (yield: 94.0%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccnnc1.c1ccccc1.C1C[NH]CC[NH]1 | MsOH.HO- | null | null | null | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1>>CC(C)Cn1nc(-c2ccc(F)cc2F)cc(CN2CCN(C)CC2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-94f9a2de92fb4bf98791169184bbb5e3 | CC(C)(C)OC(=O)N1CCNCC1.CC(C)Cn1nc(-c2ccc(F)cc2F)cc(COS(C)(=O)=O)c1=O>>CC(C)Cn1nc(-c2ccc(F)cc2F)cc(CN2CCN(C(=O)OC(C)(C)C)CC2)c1=O | N1(CCNCC1)C(=O)OC(C)(C)C.C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=C(C=C(C=C1)F)F)CC(C)C)=O | [NH:19]1[CH2:20][CH2:21][N:22]([C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:30][CH2:31]1.CS(=O)(=O)O[CH2:18][c:17]1[cH:16][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][c:14]2[F:15])[n:6][n:5]([CH2:4][CH:2]([CH3:1])[CH3:3])[c:32]1=[O:33]>>[CH3:1][CH:2]([CH3:3])[CH2:4][n:5]1[n:6][c:7](-[c:8]2[cH:9][cH:1... | CC(C)(C)OC(=O)N1CCNCC1.CC(C)Cn1nc(-c2ccc(F)cc2F)cc(COS(C)(=O)=O)c1=O | CC(C)Cn1nc(-c2ccc(F)cc2F)cc(CN2CCN(C(=O)OC(C)(C)C)CC2)c1=O | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1[nH]nc(-c2ccccc2)cc1CN1CCNCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 97.5 | [{"value": 97.5, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 6-(2,4-difluorophenyl)-2-isobutyl-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and tert-butyl 1-piperazinecarboxylate were reacted to yield the title compound as a slightly yellow oil (yield: 97.5%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccnnc1.c1ccccc1.C1C[NH]CC[NH]1 | MsOH.HO- | null | null | null | CC(C)(C)OC(=O)N1CCNCC1.CC(C)Cn1nc(-c2ccc(F)cc2F)cc(COS(C)(=O)=O)c1=O>>CC(C)Cn1nc(-c2ccc(F)cc2F)cc(CN2CCN(C(=O)OC(C)(C)C)CC2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c691731ee11f4e87b3c2983c4e59d2bb | COC(=O)c1cc(-c2ccc(F)c(C)c2)n[nH]c1=O.ClCc1ccccc1>>COC(=O)c1cc(-c2ccc(F)c(C)c2)nn(Cc2ccccc2)c1=O | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CO.FC1=C(C=C(C=C1)C=1C=C(C(NN1)=O)C(=O)OC)C.C(C1=CC=CC=C1)Cl>>C(C1=CC=CC=C1)N1N=C(C=C(C1=O)C(=O)OC)C1=CC(=C(C=C1)F)C | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[c:13]([CH3:14])[cH:15]2)[n:16][nH:17][c:25]1=[O:26].Cl[CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[c:13]([CH3:14])[cH:15]2)[n:16][n:17]([CH2:18][c:19]2[cH:2... | COC(=O)c1cc(-c2ccc(F)c(C)c2)n[nH]c1=O.ClCc1ccccc1 | COC(=O)c1cc(-c2ccc(F)c(C)c2)nn(Cc2ccccc2)c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 456217c8bdd4490079dbc0339e1b1eedc560d0b24ec9d54c4ed1fbd8e71fb3dc | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[nH;D2;+0:11]:[#7;a:12]:[c:13]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[#7;a:12]:[c:13] | 71 | [{"value": 71.0, "product": "C(C1=CC=CC=C1)N1N=C(C=C(C1=O)C(=O)OC)C1=CC(=C(C=C1)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (6), 6-(4-fluoro-3-methylphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one and benzyl chloride were reacted to yield the title compound as yellow needles (yield: 71.0%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnncc1 | c1ccnnc1 | c1ccnnc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | COC(=O)c1cc(-c2ccc(F)c(C)c2)n[nH]c1=O.ClCc1ccccc1>>COC(=O)c1cc(-c2ccc(F)c(C)c2)nn(Cc2ccccc2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e4cb384438354d1495d3e3a819bb7dae | COC(=O)c1cc(-c2ccc(F)c(C)c2)nn(Cc2ccccc2)c1=O>>Cc1cc(-c2cc(C(=O)O)c(=O)n(Cc3ccccc3)n2)ccc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.C(C1=CC=CC=C1)N1N=C(C=C(C1=O)C(=O)OC)C1=CC(=C(C=C1)F)C>>C(C1=CC=CC=C1)N1N=C(C=C(C1=O)C(=O)O)C1=CC(=C(C=C1)F)C | C[O:10][C:8]([c:7]1[cH:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:24]([F:25])[cH:23][cH:22]2)[n:21][n:13]([CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[c:11]1=[O:12])=[O:9]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([C:8](=[O:9])[OH:10])[c:11](=[O:12])[n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[n:21... | COC(=O)c1cc(-c2ccc(F)c(C)c2)nn(Cc2ccccc2)c1=O | Cc1cc(-c2cc(C(=O)O)c(=O)n(Cc3ccccc3)n2)ccc1F | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 65.2 | [{"value": 65.2, "product": "C(C1=CC=CC=C1)N1N=C(C=C(C1=O)C(=O)O)C1=CC(=C(C=C1)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (7), 2-benzyl-6-(4-fluoro-3-methylphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one was reacted to yield the title compound as a pale yellow crystalline powder (yield: 65.2%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(-c2ccc(F)c(C)c2)nn(Cc2ccccc2)c1=O>>Cc1cc(-c2cc(C(=O)O)c(=O)n(Cc3ccccc3)n2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e966cf0212f84b11abd2ff6fc6332c91 | Cc1cc(-c2cc(C(=O)O)c(=O)n(Cc3ccccc3)n2)ccc1F>>Cc1cc(-c2cc(CO)c(=O)n(Cc3ccccc3)n2)ccc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CN1C(C=2C(C1=O)=CC=CC2)=O.C(C1=CC=CC=C1)N1N=C(C=C(C1=O)C(=O)O)C1=CC(=C(C=C1)F)C>>C(C1=CC=CC=C1)N1N=C(C=C(C1=O)CO)C1=CC(=C(C=C1)F)C | O=[C:8]([c:7]1[cH:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:23]([F:24])[cH:22][cH:21]2)[n:20][n:12]([CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:10]1=[O:11])[OH:9]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([CH2:8][OH:9])[c:10](=[O:11])[n:12]([CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[n:20]2)[cH:21][c... | Cc1cc(-c2cc(C(=O)O)c(=O)n(Cc3ccccc3)n2)ccc1F | Cc1cc(-c2cc(CO)c(=O)n(Cc3ccccc3)n2)ccc1F | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10]>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:9]:1=[O;D1;H0:10] | 28.4 | [{"value": 28.4, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 2-benzyl-4-carboxy-6-(4-fluoro-3-methylphenyl)-2H-pyridazin-3-one was reacted to yield the title compound as slightly yellow needles (yield: 28.4%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | Other | null | null | null | Cc1cc(-c2cc(C(=O)O)c(=O)n(Cc3ccccc3)n2)ccc1F>>Cc1cc(-c2cc(CO)c(=O)n(Cc3ccccc3)n2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4ff9cb33be7e4153becfd1f708da72b0 | CC(C)(C)OC(=O)N1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccccc3)n2)ccc1F>>Cc1cc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(Cc3ccccc3)n2)ccc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C(C1=CC=CC=C1)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC(=C(C=C1)F)C.N1(CCNCC1)C(=O)OC(C)(C)C>>C(C1=CC=CC=C1)N1N=C(C=C(C1=O)CN1CCN(CC1)C(=O)OC(C)(C)C)C1=CC(=C(C=C1)F)C | [NH:9]1[CH2:10][CH2:11][N:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[CH2:20][CH2:21]1.CS(=O)(=O)O[CH2:8][c:7]1[cH:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:35]([F:36])[cH:34][cH:33]2)[n:32][n:24]([CH2:25][c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[c:22]1=[O:23]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7... | CC(C)(C)OC(=O)N1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccccc3)n2)ccc1F | Cc1cc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(Cc3ccccc3)n2)ccc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1Cc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 91.8 | [{"value": 91.8, "product": "C(C1=CC=CC=C1)N1N=C(C=C(C1=O)CN1CCN(CC1)C(=O)OC(C)(C)C)C1=CC(=C(C=C1)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-benzyl-6-(4-fluoro-3-methylphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and tert-butyl 1-piperazinecarboxylate were reacted to yield the title compound as a yellow oil (yield: 91.8%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.c1ccccc1 | MsOH.HO- | null | null | null | CC(C)(C)OC(=O)N1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccccc3)n2)ccc1F>>Cc1cc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(Cc3ccccc3)n2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-114c079f419d48ed852795480fd58e9b | CN1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccccc3)n2)ccc1F>>Cc1cc(-c2cc(CN3CCN(C)CC3)c(=O)n(Cc3ccccc3)n2)ccc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C(C1=CC=CC=C1)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC(=C(C=C1)F)C.CN1CCNCC1>>C(C1=CC=CC=C1)N1N=C(C=C(C1=O)CN1CCN(CC1)C)C1=CC(=C(C=C1)F)C | [NH:9]1[CH2:10][CH2:11][N:12]([CH3:13])[CH2:14][CH2:15]1.CS(=O)(=O)O[CH2:8][c:7]1[cH:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:29]([F:30])[cH:28][cH:27]2)[n:26][n:18]([CH2:19][c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:16]1=[O:17]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([CH2:8][N:9]3[CH2:10][CH2:11][N:12]([CH3:13])... | CN1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccccc3)n2)ccc1F | Cc1cc(-c2cc(CN3CCN(C)CC3)c(=O)n(Cc3ccccc3)n2)ccc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1Cc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 81.3 | [{"value": 81.3, "product": "C(C1=CC=CC=C1)N1N=C(C=C(C1=O)CN1CCN(CC1)C)C1=CC(=C(C=C1)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-benzyl-6-(4-fluoro-3-methylphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 81.3%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.c1ccccc1 | MsOH.HO- | null | null | null | CN1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccccc3)n2)ccc1F>>Cc1cc(-c2cc(CN3CCN(C)CC3)c(=O)n(Cc3ccccc3)n2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-ab159311283c473e80d4c3406696396e | CNC.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccccc3)n2)ccc1F>>Cc1cc(-c2cc(CN(C)C)c(=O)n(Cc3ccccc3)n2)ccc1F | C(C1=CC=CC=C1)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC(=C(C=C1)F)C.CNC>>C(C1=CC=CC=C1)N1N=C(C=C(C1=O)CN(C)C)C1=CC(=C(C=C1)F)C | [NH:9]([CH3:10])[CH3:11].CS(=O)(=O)O[CH2:8][c:7]1[cH:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:25]([F:26])[cH:24][cH:23]2)[n:22][n:14]([CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:12]1=[O:13]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([CH2:8][N:9]([CH3:10])[CH3:11])[c:12](=[O:13])[n:14]([CH2:15][c:16]3[cH:17][c... | CNC.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccccc3)n2)ccc1F | Cc1cc(-c2cc(CN(C)C)c(=O)n(Cc3ccccc3)n2)ccc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C;D1;H3:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:11](-[C;D1;H3:10])-[C;D1;H3:12]):[c:8]:1=[O;D1;H0:9] | 92.7 | [{"value": 92.7, "product": "C(C1=CC=CC=C1)N1N=C(C=C(C1=O)CN(C)C)C1=CC(=C(C=C1)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 7, 2-benzyl-6-(4-fluoro-3-methylphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and dimethylamine were reacted to yield the title compound as a yellow oil (yield: 92.7%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | MsOH.HO- | null | null | null | CNC.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccccc3)n2)ccc1F>>Cc1cc(-c2cc(CN(C)C)c(=O)n(Cc3ccccc3)n2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fcf274a54078452a9ad50b4702e61f52 | COC(=O)c1cc(-c2ccc(F)c(C)c2)nn(CC=Cc2ccccc2)c1=O>>Cc1cc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccccc3)n2)ccc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.C(C=CC1=CC=CC=C1)N1N=C(C=C(C1=O)C(=O)OC)C1=CC(=C(C=C1)F)C>>C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)F)C)CC=CC1=CC=CC=C1)=O | C[O:10][C:8]([c:7]1[cH:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:26]([F:27])[cH:25][cH:24]2)[n:23][n:13]([CH2:14][CH:15]=[CH:16][c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[c:11]1=[O:12])=[O:9]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([C:8](=[O:9])[OH:10])[c:11](=[O:12])[n:13]([CH2:14][CH:15]=[CH:16][c:17]3[cH:18][cH:1... | COC(=O)c1cc(-c2ccc(F)c(C)c2)nn(CC=Cc2ccccc2)c1=O | Cc1cc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccccc3)n2)ccc1F | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccccc2)nn1CC=Cc1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 85.1 | [{"value": 85.1, "product": "C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)F)C)CC=CC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (7), 2-cinnamyl-6-(4-fluoro-3-methylphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one was reacted to yield the title compound as pale yellow needles (yield: 85.1%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(-c2ccc(F)c(C)c2)nn(CC=Cc2ccccc2)c1=O>>Cc1cc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccccc3)n2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-535ad6d41210447d8a3bfdad5a29b12b | Cc1cc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccccc3)n2)ccc1F>>Cc1cc(-c2cc(CO)c(=O)n(CC=Cc3ccccc3)n2)ccc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CN1C(C=2C(C1=O)=CC=CC2)=O.C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)F)C)CC=CC1=CC=CC=C1)=O>>C(C=CC1=CC=CC=C1)N1N=C(C=C(C1=O)CO)C1=CC(=C(C=C1)F)C | O=[C:8]([c:7]1[cH:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:25]([F:26])[cH:24][cH:23]2)[n:22][n:12]([CH2:13][CH:14]=[CH:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[c:10]1=[O:11])[OH:9]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([CH2:8][OH:9])[c:10](=[O:11])[n:12]([CH2:13][CH:14]=[CH:15][c:16]3[cH:17][cH:18][cH:19][cH... | Cc1cc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccccc3)n2)ccc1F | Cc1cc(-c2cc(CO)c(=O)n(CC=Cc3ccccc3)n2)ccc1F | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)nn1CC=Cc1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]-[C:9]=[C:10]):[c:11]:1=[O;D1;H0:12]>>[C:10]=[C:9]-[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:11]:1=[O;D1;H0:12] | 20.1 | [{"value": 20.1, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-carboxy-2-cinnamyl-6-(4-fluoro-3-methylphenyl)-2H-pyridazin-3-one was reacted to yield the title compound as slightly yellow needles (yield: 20.1%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | Other | null | null | null | Cc1cc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccccc3)n2)ccc1F>>Cc1cc(-c2cc(CO)c(=O)n(CC=Cc3ccccc3)n2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5b6ac077267d492e850168ceef9333fb | CC(C)(C)OC(=O)N1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccccc3)n2)ccc1F.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1cc(-c2nn(CC=Cc3ccccc3)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)ccc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C(C=CC1=CC=CC=C1)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC(=C(C=C1)F)C.N1(CCNCC1)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)F)C)CC=CC1=CC=CC=C1)=O | [NH:20]1[CH2:21][CH2:22][N:23]([C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:31][CH2:32]1.CS(=O)(=O)OC[c:19]1[c:17](=[O:18])[n:7]([CH2:8][CH:9]=[CH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[n:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:37]([F:38])[cH:36][cH:35]2)[cH:33]1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(... | CC(C)(C)OC(=O)N1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccccc3)n2)ccc1F.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F | Cc1cc(-c2nn(CC=Cc3ccccc3)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)ccc1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2a0dbc48e846de8e0c36eabe2ecaa3dda67e2c62a942dd827dcb6cda2589c033 | f8979a7dc32618975f84bf1d08d0eb1a0766a30fc7e3bcdfee8ffc6d86d4188b | O=c1c(N2CCNCC2)cc(-c2ccccc2)nn1CC=Cc1ccccc1 | C-C(-C)-C-n1:n:c(-c2:c:c:c(-C):c(-F):c:2):c(-[CH3;D1;+0:1]):c(-N2-C-C-N(-C(=O)-O-C(-C)(-C)-C)-C-C-2):c:1=O.C-S(=O)(=O)-O-C-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c:4](-[c:5]):[#7;a:6]:[#7;a:7](-[C:8]-[C:9]=[C:10]):[c:11]:1=[O;D1;H0:12].[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[C:10]=[C:9]-[C:8]-[#7;a:7]1:[#7;a:6]:[... | 86.7 | [{"value": 86.7, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)F)C)CC=CC1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-cinnamyl-6-(4-fluoro-3-methylphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and tert-butyl 1-piperazinecarboxylate were reacted to yield the title compound as a yellow oil (yield: 86.7%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic halide.Carbamic ester.Ether.Secondary amine.Tertiary amine.Boc | Tertiary amine | C1CNCC[NH]1.c1ccnnc1.c1ccccc1.c1ccnnc1.C1CNCCN1 | c1ccnnc1.C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.c1ccccc1.C1C[NH]CC[NH]1 | MsOH.HF | null | null | null | CC(C)(C)OC(=O)N1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccccc3)n2)ccc1F.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1cc(-c2nn(CC=Cc3ccccc3)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-5efab2f861dd4da19edc62163b941916 | CN1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccccc3)n2)ccc1F>>Cc1cc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC=Cc3ccccc3)n2)ccc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C(C=CC1=CC=CC=C1)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC(=C(C=C1)F)C.CN1CCNCC1>>C(C=CC1=CC=CC=C1)N1N=C(C=C(C1=O)CN1CCN(CC1)C)C1=CC(=C(C=C1)F)C | [NH:9]1[CH2:10][CH2:11][N:12]([CH3:13])[CH2:14][CH2:15]1.CS(=O)(=O)O[CH2:8][c:7]1[cH:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:31]([F:32])[cH:30][cH:29]2)[n:28][n:18]([CH2:19][CH:20]=[CH:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[c:16]1=[O:17]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([CH2:8][N:9]3[CH2:10][CH2:11][... | CN1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccccc3)n2)ccc1F | Cc1cc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC=Cc3ccccc3)n2)ccc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1CC=Cc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]-[C:8]=[C:9]):[c:10]:1=[O;D1;H0:11].[#7:12]1-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-1>>[C:9]=[C:8]-[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:15]2-[C:14]-[C:13]-[#7:12]-[C:17]-[C:16]-2):[c:10]:1=[O;D1;H0:11] | 80.1 | [{"value": 80.1, "product": "C(C=CC1=CC=CC=C1)N1N=C(C=C(C1=O)CN1CCN(CC1)C)C1=CC(=C(C=C1)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-cinnamyl-6-(4-fluoro-3-methylphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 80.1%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.c1ccccc1 | MsOH.HO- | null | null | null | CN1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccccc3)n2)ccc1F>>Cc1cc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC=Cc3ccccc3)n2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9099d3a220c64814acf549559f07b0ba | CNC.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccccc3)n2)ccc1F>>Cc1cc(-c2cc(CN(C)C)c(=O)n(CC=Cc3ccccc3)n2)ccc1F | C(C=CC1=CC=CC=C1)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC(=C(C=C1)F)C.CNC>>C(C=CC1=CC=CC=C1)N1N=C(C=C(C1=O)CN(C)C)C1=CC(=C(C=C1)F)C | [NH:9]([CH3:10])[CH3:11].CS(=O)(=O)O[CH2:8][c:7]1[cH:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:27]([F:28])[cH:26][cH:25]2)[n:24][n:14]([CH2:15][CH:16]=[CH:17][c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[c:12]1=[O:13]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([CH2:8][N:9]([CH3:10])[CH3:11])[c:12](=[O:13])[n:14]([CH2:15][... | CNC.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccccc3)n2)ccc1F | Cc1cc(-c2cc(CN(C)C)c(=O)n(CC=Cc3ccccc3)n2)ccc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1ccc(-c2ccccc2)nn1CC=Cc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]-[C:8]=[C:9]):[c:10]:1=[O;D1;H0:11].[C;D1;H3:12]-[NH;D2;+0:13]-[C;D1;H3:14]>>[C:9]=[C:8]-[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13](-[C;D1;H3:12])-[C;D1;H3:14]):[c:10]:1=[O;D1;H0:11] | 90.9 | [{"value": 90.9, "product": "C(C=CC1=CC=CC=C1)N1N=C(C=C(C1=O)CN(C)C)C1=CC(=C(C=C1)F)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 7, 2-cinnamyl-6-(4-fluoro-3-methylphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and dimethylamine were reacted to yield the title compound as a yellow oil (yield: 90.9%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | MsOH.HO- | null | null | null | CNC.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccccc3)n2)ccc1F>>Cc1cc(-c2cc(CN(C)C)c(=O)n(CC=Cc3ccccc3)n2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-24c70d4868564ed4aaa651e7184c89a3 | COC(=O)c1cc(-c2ccc(F)c(C)c2)nn(CC=Cc2ccc(Cl)cc2)c1=O>>Cc1cc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)ccc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.ClC1=CC=C(C=CCN2N=C(C=C(C2=O)C(=O)OC)C2=CC(=C(C=C2)F)C)C=C1>>C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)F)C)CC=CC1=CC=C(C=C1)Cl)=O | C[O:10][C:8]([c:7]1[cH:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:27]([F:28])[cH:26][cH:25]2)[n:24][n:13]([CH2:14][CH:15]=[CH:16][c:17]2[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]2)[c:11]1=[O:12])=[O:9]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([C:8](=[O:9])[OH:10])[c:11](=[O:12])[n:13]([CH2:14][CH:15]=[CH:16][c:17]3[cH:... | COC(=O)c1cc(-c2ccc(F)c(C)c2)nn(CC=Cc2ccc(Cl)cc2)c1=O | Cc1cc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)ccc1F | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccccc2)nn1CC=Cc1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 86.2 | [{"value": 86.2, "product": "C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)F)C)CC=CC1=CC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (7), 2-(4-chloro-cinnamyl)-6-(4-fluoro-3-methylphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one was reacted to yield the title compound as a yellow crystalline powder (yield: 86.2%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(-c2ccc(F)c(C)c2)nn(CC=Cc2ccc(Cl)cc2)c1=O>>Cc1cc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f3e9efc20bd94e9a93ba445badfcb9d1 | Cc1cc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)ccc1F>>Cc1cc(-c2cc(CO)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)ccc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CN1C(C=2C(C1=O)=CC=CC2)=O.C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)F)C)CC=CC1=CC=C(C=C1)Cl)=O>>ClC1=CC=C(C=CCN2N=C(C=C(C2=O)CO)C2=CC(=C(C=C2)F)C)C=C1 | O=[C:8]([c:7]1[cH:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:26]([F:27])[cH:25][cH:24]2)[n:23][n:12]([CH2:13][CH:14]=[CH:15][c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[c:10]1=[O:11])[OH:9]>>[CH3:1][c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([CH2:8][OH:9])[c:10](=[O:11])[n:12]([CH2:13][CH:14]=[CH:15][c:16]3[cH:17][cH:18][c... | Cc1cc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)ccc1F | Cc1cc(-c2cc(CO)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)ccc1F | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)nn1CC=Cc1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]-[C:9]=[C:10]):[c:11]:1=[O;D1;H0:12]>>[C:10]=[C:9]-[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:11]:1=[O;D1;H0:12] | 17.2 | [{"value": 17.2, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-carboxy-2-(4-chlorocinnamyl)-6-(4-fluoro-3-methylphenyl)-2H-pyridazin-3-one was reacted to yield the title compound as slightly yellow needles (yield: 17.2%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | Other | null | null | null | Cc1cc(-c2cc(C(=O)O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)ccc1F>>Cc1cc(-c2cc(CO)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6b78883984ef40e189d6eb0eb0ecab88 | CC(C)(C)OC(=O)N1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)ccc1F.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1cc(-c2nn(CC=Cc3ccc(Cl)cc3)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)ccc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.ClC1=CC=C(C=CCN2N=C(C=C(C2=O)COS(=O)(=O)C)C2=CC(=C(C=C2)F)C)C=C1.N1(CCNCC1)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)F)C)CC=CC1=CC=C(C=C1)Cl)=O | [NH:21]1[CH2:22][CH2:23][N:24]([C:25](=[O:26])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH2:32][CH2:33]1.CS(=O)(=O)OC[c:20]1[c:18](=[O:19])[n:7]([CH2:8][CH:9]=[CH:10][c:11]2[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]2)[n:6][c:5](-[c:4]2[cH:3][c:2]([CH3:1])[c:38]([F:39])[cH:37][cH:36]2)[cH:34]1.Cc1ccc(-c2nn(CC(C)C)c(=O)... | CC(C)(C)OC(=O)N1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)ccc1F.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F | Cc1cc(-c2nn(CC=Cc3ccc(Cl)cc3)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)ccc1F | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2a0dbc48e846de8e0c36eabe2ecaa3dda67e2c62a942dd827dcb6cda2589c033 | f8979a7dc32618975f84bf1d08d0eb1a0766a30fc7e3bcdfee8ffc6d86d4188b | O=c1c(N2CCNCC2)cc(-c2ccccc2)nn1CC=Cc1ccccc1 | C-C(-C)-C-n1:n:c(-c2:c:c:c(-C):c(-F):c:2):c(-[CH3;D1;+0:1]):c(-N2-C-C-N(-C(=O)-O-C(-C)(-C)-C)-C-C-2):c:1=O.C-S(=O)(=O)-O-C-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c:4](-[c:5]):[#7;a:6]:[#7;a:7](-[C:8]-[C:9]=[C:10]):[c:11]:1=[O;D1;H0:12].[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[C:10]=[C:9]-[C:8]-[#7;a:7]1:[#7;a:6]:[... | 87.9 | [{"value": 87.9, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)F)C)CC=CC1=CC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-(4-chlorocinnamyl)-6-(4-fluoro-3-methylphenyl)-4-methane-sulfonyloxymethyl-2H-pyridazin-3-one and tert-butyl 1-piperazinecarboxylate were reacted to yield the title compound as a yellow oil (yield: 87.9%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacte... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic halide.Carbamic ester.Ether.Secondary amine.Tertiary amine.Boc | Tertiary amine | C1CNCC[NH]1.c1ccnnc1.c1ccccc1.c1ccnnc1.C1CNCCN1 | c1ccnnc1.C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.c1ccccc1.C1C[NH]CC[NH]1 | MsOH.HF | null | null | null | CC(C)(C)OC(=O)N1CCNCC1.Cc1cc(-c2cc(COS(C)(=O)=O)c(=O)n(CC=Cc3ccc(Cl)cc3)n2)ccc1F.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1cc(-c2nn(CC=Cc3ccc(Cl)cc3)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)ccc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-abb0a210dd504a5dadf137cc2aaedd23 | COC(=O)c1cc(-c2ccc(SC)cc2)nn(CC2CC2)c1=O>>CSc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CC3)n2)cc1 | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.C1(CC1)CN1N=C(C=C(C1=O)C(=O)OC)C1=CC=C(C=C1)SC>>C(=O)(O)C=1C(N(N=C(C1)C1=CC=C(C=C1)SC)CC1CC1)=O | C[O:12][C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([S:2][CH3:1])[cH:22][cH:21]2)[n:20][n:15]([CH2:16][CH:17]2[CH2:18][CH2:19]2)[c:13]1=[O:14])=[O:11]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13](=[O:14])[n:15]([CH2:16][CH:17]3[CH2:18][CH2:19]3)[n:20]2)[cH:21][cH:22]1 | COC(=O)c1cc(-c2ccc(SC)cc2)nn(CC2CC2)c1=O | CSc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CC3)n2)cc1 | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccccc2)nn1CC1CC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 98.2 | [{"value": 98.2, "product": "C(=O)(O)C=1C(N(N=C(C1)C1=CC=C(C=C1)SC)CC1CC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (7), 2-cyclopropylmethyl-4-methoxycarbonyl-6-[4-(methylthio)-phenyl]-2H-pyridazin-3-one was reacted to yield the title compound as a yellow crystalline powder (yield: 98.2%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccnnc1.C1CC1 | Other | null | null | null | COC(=O)c1cc(-c2ccc(SC)cc2)nn(CC2CC2)c1=O>>CSc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CC3)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-45b35999b6f84963bf5a02dbc2d4b406 | CSc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CC3)n2)cc1>>CSc1ccc(-c2cc(CO)c(=O)n(CC3CC3)n2)cc1 | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CN1C(C=2C(C1=O)=CC=CC2)=O.C(=O)(O)C=1C(N(N=C(C1)C1=CC=C(C=C1)SC)CC1CC1)=O>>C1(CC1)CN1N=C(C=C(C1=O)CO)C1=CC=C(C=C1)SC | O=[C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([S:2][CH3:1])[cH:21][cH:20]2)[n:19][n:14]([CH2:15][CH:16]2[CH2:17][CH2:18]2)[c:12]1=[O:13])[OH:11]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][OH:11])[c:12](=[O:13])[n:14]([CH2:15][CH:16]3[CH2:17][CH2:18]3)[n:19]2)[cH:20][cH:21]1 | CSc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CC3)n2)cc1 | CSc1ccc(-c2cc(CO)c(=O)n(CC3CC3)n2)cc1 | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)nn1CC1CC1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10]>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:9]:1=[O;D1;H0:10] | 22.6 | [{"value": 22.6, "product": "C1(CC1)CN1N=C(C=C(C1=O)CO)C1=CC=C(C=C1)SC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-carboxy-2-cyclopropylmethyl-6-[4-(methylthio)phenyl]-2H-pyridazin-3-one was reacted to yield the title compound as a pale yellow crystalline powder (yield: 22.6%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccnnc1.C1CC1 | Other | null | null | null | CSc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CC3)n2)cc1>>CSc1ccc(-c2cc(CO)c(=O)n(CC3CC3)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-dac97961ada8488e8c17f9181fc1ba4d | CN1CCNCC1.CSc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1>>CSc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC3CC3)n2)cc1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C1(CC1)CN1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)SC.CN1CCNCC1>>C1(CC1)CN1N=C(C=C(C1=O)CN1CCN(CC1)C)C1=CC=C(C=C1)SC | [NH:11]1[CH2:12][CH2:13][N:14]([CH3:15])[CH2:16][CH2:17]1.CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([S:2][CH3:1])[cH:27][cH:26]2)[n:25][n:20]([CH2:21][CH:22]2[CH2:23][CH2:24]2)[c:18]1=[O:19]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][N:11]3[CH2:12][CH2:13][N:14]([CH3:15])[CH2:1... | CN1CCNCC1.CSc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1 | CSc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC3CC3)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1CC1CC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 85.7 | [{"value": 85.7, "product": "C1(CC1)CN1N=C(C=C(C1=O)CN1CCN(CC1)C)C1=CC=C(C=C1)SC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-cyclopropylmethyl-4-methanesulfonyloxymethyl-6-[4-(methylthio)phenyl]-2H-pyridazin-3-one and 1-methyl-piperazine were reacted to yield the title compound as a yellow oil (yield: 85.7 %)
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.C1CC1 | MsOH.HO- | null | null | null | CN1CCNCC1.CSc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CC3)n2)cc1>>CSc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC3CC3)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-91f9a9d242cc4d829d962d9a6373321d | CC(C)CBr.COC(=O)c1cc(-c2ccc(SC)cc2)n[nH]c1=O>>CSc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1 | C(O)([O-])=O.[Na+].COC(=O)C=1C(NN=C(C1)C1=CC=C(C=C1)SC)=O.C([O-])([O-])=O.[K+].[K+].C(C(C)C)Br>>C(=O)(O)C=1C(N(N=C(C1)C1=CC=C(C=C1)SC)CC(C)C)=O | Br[CH2:16][CH:17]([CH3:18])[CH3:19].C[O:12][C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([S:2][CH3:1])[cH:22][cH:21]2)[n:20][nH:15][c:13]1=[O:14])=[O:11]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13](=[O:14])[n:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[n:20]2)[cH:21][cH:22]1 | CC(C)CBr.COC(=O)c1cc(-c2ccc(SC)cc2)n[nH]c1=O | CSc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1 | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 5657c51de7724c63a786ad9d48deb9204ebd7b0734782c9118f1c3d5800dec03 | bb8c9cbffd0728fccf6e94a36c447b744f8891f8faf7c54ceec728809fb06a61 | O=c1ccc(-c2ccccc2)n[nH]1 | Br-[CH2;D2;+0:1]-[C:2](-[C;D1;H3:3])-[C;D1;H3:4].C-[O;H0;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[nH;D2;+0:11]:[#7;a:12]:[c:13]>>[C;D1;H3:3]-[C:2](-[C;D1;H3:4])-[CH2;D2;+0:1]-[n;H0;D3;+0:11](:[#7;a:12]:[c:13]):[c:9](=[O;D1;H0:10]):[c:8]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:5] | 65.1 | [{"value": 65.1, "product": "C(=O)(O)C=1C(N(N=C(C1)C1=CC=C(C=C1)SC)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 2 | HOUR | To a solution of 4-methoxycarbonyl-6-[4-(methylthio)-phenyl]-2H-pyridazin-3-one (8.00 g, 29.0 mmol) in N,N-dimethylformamide (80 mL) were added potassium carbonate (8.02 g, 58.0 mmol) and isobutyl bromide (4.76 g, 34.8 mmol), and the mixture was stirred at 80° C. for 2 hours. The temperature of the reaction mixture was... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester | Carboxylic acid | c1cnncc1 | c1ccnnc1 | c1ccccc1.c1ccnnc1 | HBr | CN(C=O)C | 80 | 2 | CC(C)CBr.COC(=O)c1cc(-c2ccc(SC)cc2)n[nH]c1=O>CN(C=O)C>CSc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-4890823ff7fb4745a8939acecea10f65 | CSc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1>>CSc1ccc(-c2cc(CO)c(=O)n(CC(C)C)n2)cc1 | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CN1C(C=2C(C1=O)=CC=CC2)=O.C(=O)(O)C=1C(N(N=C(C1)C1=CC=C(C=C1)SC)CC(C)C)=O>>OCC=1C(N(N=C(C1)C1=CC=C(C=C1)SC)CC(C)C)=O | O=[C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([S:2][CH3:1])[cH:21][cH:20]2)[n:19][n:14]([CH2:15][CH:16]([CH3:17])[CH3:18])[c:12]1=[O:13])[OH:11]>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][OH:11])[c:12](=[O:13])[n:14]([CH2:15][CH:16]([CH3:17])[CH3:18])[n:19]2)[cH:20][cH:21]1 | CSc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1 | CSc1ccc(-c2cc(CO)c(=O)n(CC(C)C)n2)cc1 | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)n[nH]1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10]>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:9]:1=[O;D1;H0:10] | 35.3 | [{"value": 35.3, "product": "OCC=1C(N(N=C(C1)C1=CC=C(C=C1)SC)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-carboxy-2-isobutyl-6-[4-(methylthio)phenyl]-2H-pyridazin-3-one was reacted to yield the title compound as a yellow oil (yield: 35.3%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccnnc1 | Other | null | null | null | CSc1ccc(-c2cc(C(=O)O)c(=O)n(CC(C)C)n2)cc1>>CSc1ccc(-c2cc(CO)c(=O)n(CC(C)C)n2)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-beeed6c788104ac49612491fac170148 | CN1CCNCC1.CSc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>CSc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C)CC3)c2C)cc1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)SC.CN1CCNCC1>>C(C(C)C)N1N=C(C(=C(C1=O)N1CCN(CC1)C)C)C1=CC=C(C=C1)SC | C1C[N:20]([CH3:21])[CH2:19]CN1.CC(C)Cn1nc(-c2c[cH:4][c:3]([S:2][CH3:1])[cH:27]c2)cc(COS(C)(=O)=O)c1=O.Cc1c[cH:5][c:6](-[c:7]2[n:8][n:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[c:14](=[O:15])[c:16]([N:17]3[CH2:18]CN(C(=O)OC(C)(C)C)[CH2:22][CH2:23]3)[c:24]2[CH3:25])[cH:26]c1F>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][... | CN1CCNCC1.CSc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F | CSc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C)CC3)c2C)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b575abea58eaae4f278ac3e30dfd9628b62a316f312c67692a18c9045c141889 | f8979a7dc32618975f84bf1d08d0eb1a0766a30fc7e3bcdfee8ffc6d86d4188b | O=c1[nH]nc(-c2ccccc2)cc1N1CCNCC1 | C-C(-C)-C-n1:n:c(-c2:c:[cH;D2;+0:1]:[c:2](-[#16:3]):[cH;D2;+0:4]:c:2):c:c(-C-O-S(-C)(=O)=O):c:1=O.C-c1:c:[cH;D2;+0:5]:[c:6](-[c:7]:[#7;a:8]:[#7;a:9]:[c:10]:[c:11]-[#7:12]2-[C:13]-[CH2;D2;+0:14]-N(-C(=O)-O-C(-C)(-C)-C)-C-[CH2;D2;+0:15]-2):[cH;D2;+0:16]:c:1-F.[C;D1;H3:17]-[N;H0;D3;+0:18]1-C-C-N-C-[CH2;D2;+0:19]-1>>[#16:3... | 68.3 | [{"value": 68.3, "product": "C(C(C)C)N1N=C(C(=C(C1=O)N1CCN(CC1)C)C)C1=CC=C(C=C1)SC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-isobutyl-4-methanesulfonyloxymethyl-6-[4-(methylthio)phenyl]-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 68.3%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic halide.Carbamic ester.Ether.Secondary amine.Tertiary amine.Boc | Tertiary amine | C1CNCC[NH]1.c1ccnnc1.c1ccccc1.c1ccccc1.C1C[NH]CCN1 | c1ccccc1.C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1 | MsOH.HF | null | null | null | CN1CCNCC1.CSc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>CSc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C)CC3)c2C)cc1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a9661dee056c4c05b72bf31d6715bdc3 | C#CCN.CSc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1>>C#CCNCc1cc(-c2ccc(SC)cc2)nn(CC(C)C)c1=O | C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)SC.C(C#C)N>>C(C(C)C)N1N=C(C=C(C1=O)CNCC#C)C1=CC=C(C=C1)SC | [CH:1]#[C:2][CH2:3][NH2:4].CS(=O)(=O)O[CH2:5][c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([S:13][CH3:14])[cH:15][cH:16]2)[n:17][n:18]([CH2:19][CH:20]([CH3:21])[CH3:22])[c:23]1=[O:24]>>[CH:1]#[C:2][CH2:3][NH:4][CH2:5][c:6]1[cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([S:13][CH3:14])[cH:15][cH:16]2)[n:17][n:18]([CH2:19][CH:2... | C#CCN.CSc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1 | C#CCNCc1cc(-c2ccc(SC)cc2)nn(CC(C)C)c1=O | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | 8445343b2fb2fd8a9bc06f8532794f2ba6b99565a6e05a3bb9a4344ce2671186 | 7e6303acde8be57b43b4c6a673e1c7537b1efde90f08932e09e153dbba53a700 | O=c1ccc(-c2ccccc2)n[nH]1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C;D1;H1:10]#[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:13]-[C:12]-[C:11]#[C;D1;H1:10]):[c:8]:1=[O;D1;H0:9] | 52.2 | [{"value": 52.2, "product": "C(C(C)C)N1N=C(C=C(C1=O)CNCC#C)C1=CC=C(C=C1)SC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1(10), 2-isobutyl-4-methanesulfonyloxymethyl-6-[4-(methylthio)phenyl]-2H-pyridazin-3-one and propargylamine were reacted to yield the title compound as a yellow oil (yield: 52.2%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Primary amine | Secondary amine | null | null | c1ccnnc1.c1ccccc1 | MsOH.HO- | null | null | null | C#CCN.CSc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC(C)C)n2)cc1>>C#CCNCc1cc(-c2ccc(SC)cc2)nn(CC(C)C)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-80ed7fce2c314442ab3c85670fbca824 | CN1CCNCC1.CS(=O)c1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(C3CC3)n2)cc1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>CN1CCN(Cc2cc(-c3ccc(S(C)=O)cc3)nn(CC3CC3)c2=O)CC1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C1(CC1)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)S(=O)C.CN1CCNCC1>>C1(CC1)CN1N=C(C=C(C1=O)CN1CCN(CC1)C)C1=CC=C(C=C1)S(=O)C | [CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:27][CH2:28]1.CS(=O)(=O)O[CH2:6][c:7]1[cH:8][c:9](-[c:10]2[cH:11][cH:12][c:13]([S:14]([CH3:15])=[O:16])[cH:17][cH:18]2)[n:19][n:20]([CH:22]2[CH2:23][CH2:24]2)[c:25]1=[O:26].Cc1ccc(-c2nn([CH2:21]C(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][... | CN1CCNCC1.CS(=O)c1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(C3CC3)n2)cc1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F | CN1CCN(Cc2cc(-c3ccc(S(C)=O)cc3)nn(CC3CC3)c2=O)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | daedfd3234a67d0a187c6c54e3cd6417092e01f807dcf2ceeb0bbd8b0b212d6c | f8979a7dc32618975f84bf1d08d0eb1a0766a30fc7e3bcdfee8ffc6d86d4188b | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1CC1CC1 | C-C(-C)-[CH2;D2;+0:1]-n1:n:c(-c2:c:c:c(-C):c(-F):c:2):c(-C):c(-N2-C-C-N(-C(=O)-O-C(-C)(-C)-C)-C-C-2):c:1=O.C-S(=O)(=O)-O-[CH2;D2;+0:2]-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[n;H0;D3;+0:7](-[CH;D3;+0:8]2-[C:9]-[C:10]-2):[c:11]:1=[O;D1;H0:12].[#7:13]1-[C:14]-[C:15]-[NH;D2;+0:16]-[C:17]-[C:18]-1>>[O;D1;H0:12]=[c:11]1:[c:3](-[CH2;D2... | 60.6 | [{"value": 60.6, "product": "C1(CC1)CN1N=C(C=C(C1=O)CN1CCN(CC1)C)C1=CC=C(C=C1)S(=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-cyclopropyl-4-methanesulfonyloxymethyl-6-[4-(methyl-sulfinyl)phenyl]-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 60.6%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic halide.Carbamic ester.Ether.Secondary amine.Tertiary amine.Boc | Tertiary amine | C1C[NH]CCN1.c1ccnnc1.C1CC1.c1ccccc1.c1ccnnc1.C1CNCCN1 | C1C[NH]CC[NH]1.c1ccnnc1.C1CC1 | C1C[NH]CC[NH]1.c1ccnnc1.c1ccccc1.C1CC1 | MsOH.HF | null | null | null | CN1CCNCC1.CS(=O)c1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(C3CC3)n2)cc1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>CN1CCN(Cc2cc(-c3ccc(S(C)=O)cc3)nn(CC3CC3)c2=O)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-41795e14373e423a9737a2dafd26dc0b | CC(C)Cn1nc(-c2ccc(S(C)=O)cc2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1c(-c2ccc(S(C)=O)cc2)nn(CC(C)C)c(=O)c1N1CCN(C)CC1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)S(=O)C.CN1CCNCC1>>C(C(C)C)N1N=C(C(=C(C1=O)N1CCN(CC1)C)C)C1=CC=C(C=C1)S(=O)C | CS(=O)(=O)OC[c:21]1[cH:2][c:3](-[c:4]2[cH:5][cH:6][c:7]([S:8]([CH3:9])=[O:10])[cH:11][cH:12]2)[n:13][n:14]([CH2:15][CH:16]([CH3:17])[CH3:18])[c:19]1=[O:20].[NH:22]1[CH2:23][CH2:24][N:25]([CH3:26])[CH2:27][CH2:28]1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2[CH3:1])cc1F>>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6]... | CC(C)Cn1nc(-c2ccc(S(C)=O)cc2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F | Cc1c(-c2ccc(S(C)=O)cc2)nn(CC(C)C)c(=O)c1N1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2a0dbc48e846de8e0c36eabe2ecaa3dda67e2c62a942dd827dcb6cda2589c033 | f8979a7dc32618975f84bf1d08d0eb1a0766a30fc7e3bcdfee8ffc6d86d4188b | O=c1[nH]nc(-c2ccccc2)cc1N1CCNCC1 | C-C(-C)-C-n1:n:c(-c2:c:c:c(-C):c(-F):c:2):c(-[CH3;D1;+0:1]):c(-N2-C-C-N(-C(=O)-O-C(-C)(-C)-C)-C-C-2):c:1=O.C-S(=O)(=O)-O-C-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c:4](-[c:5]):[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:4](-[c:5]):[c;H0;D3;+0:3]... | 61.8 | [{"value": 61.8, "product": "C(C(C)C)N1N=C(C(=C(C1=O)N1CCN(CC1)C)C)C1=CC=C(C=C1)S(=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-isobutyl-4-methanesulfonyloxymethyl-6-[4-(methylsulfinyl)phenyl]-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 61.8%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic halide.Carbamic ester.Ether.Secondary amine.Tertiary amine.Boc | Tertiary amine | c1ccnnc1.C1CNCC[NH]1.c1ccccc1.c1ccnnc1.C1CNCCN1 | c1ccnnc1.C1C[NH]CC[NH]1 | c1ccnnc1.c1ccccc1.C1C[NH]CC[NH]1 | MsOH.HF | null | null | null | CC(C)Cn1nc(-c2ccc(S(C)=O)cc2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1c(-c2ccc(S(C)=O)cc2)nn(CC(C)C)c(=O)c1N1CCN(C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-51117be8824c445abd4949fe380f7aba | CNC.CS(=O)(=O)OCc1cc(-c2ccc(S(C)(=O)=O)cc2)nn(CC2CC2)c1=O>>Cc1c(-c2ccc(S(C)(=O)=O)cc2)nn(CC2CC2)c(=O)c1N(C)C | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C1(CC1)CN1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)S(=O)(=O)C.CNC>>C1(CC1)CN1N=C(C(=C(C1=O)N(C)C)C)C1=CC=C(C=C1)S(=O)(=O)C | [NH:23]([CH3:24])[CH3:25].CS(=O)(=O)O[CH2:1][c:22]1[cH:2][c:3](-[c:4]2[cH:5][cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][cH:13]2)[n:14][n:15]([CH2:16][CH:17]2[CH2:18][CH2:19]2)[c:20]1=[O:21]>>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][cH:13]2)[n:14][n:15]([CH2:16][CH:17]2[C... | CNC.CS(=O)(=O)OCc1cc(-c2ccc(S(C)(=O)=O)cc2)nn(CC2CC2)c1=O | Cc1c(-c2ccc(S(C)(=O)=O)cc2)nn(CC2CC2)c(=O)c1N(C)C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 82f622e78bec893ae4255bd5b4f122f92a6603278b6ec35a270ebdb7ddb8479c | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1ccc(-c2ccccc2)nn1CC1CC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c:4](-[c:5]):[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10].[C;D1;H3:11]-[NH;D2;+0:12]-[C;D1;H3:13]>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:4](-[c:5]):[c;H0;D3;+0:3](-[CH3;D1;+0:1]):[c;H0;D3;+0:2](-[N;H0;D3;+0:12](-[C;D1;H3:11])-[C;D1;H3:13]):[c:9]:1=[O;D1;H0:10] | 65.6 | [{"value": 65.6, "product": "C1(CC1)CN1N=C(C(=C(C1=O)N(C)C)C)C1=CC=C(C=C1)S(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-cyclopropylmethyl-4-methanesulfonyloxymethyl-6-[4-(methyl-sulfonyl)phenyl]-2H-pyridazin-3-one and dimethylamine were reacted to yield the title compound as a yellow oil (yield: 65.6%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | c1ccnnc1 | c1ccnnc1 | c1ccnnc1.c1ccccc1.C1CC1 | MsOH.HO- | null | null | null | CNC.CS(=O)(=O)OCc1cc(-c2ccc(S(C)(=O)=O)cc2)nn(CC2CC2)c1=O>>Cc1c(-c2ccc(S(C)(=O)=O)cc2)nn(CC2CC2)c(=O)c1N(C)C |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b331aaf73d044d758947cdf38450e89d | CC(C)(C)OC(=O)N1CCNCC1.CC(C)Cn1nc(-c2ccc(S(C)(=O)=O)cc2)cc(COS(C)(=O)=O)c1=O.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1c(-c2ccc(S(C)(=O)=O)cc2)nn(CC(C)C)c(=O)c1N1CCN(C(=O)OC(C)(C)C)CC1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)S(=O)(=O)C.N1(CCNCC1)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC=C(C=C1)S(=O)(=O)C)CC(C)C)=O | [NH:23]1[CH2:24][CH2:25][N:26]([C:27](=[O:28])[O:29][C:30]([CH3:31])([CH3:32])[CH3:33])[CH2:34][CH2:35]1.CC(C)Cn1nc(-[c:4]2[cH:5][cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][cH:13]2)cc(COS(C)(=O)=O)c1=O.Cc1ccc(-[c:3]2[c:2]([CH3:1])[c:22](N3CCN(C(=O)OC(C)(C)C)CC3)[c:20](=[O:21])[n:15]([CH2:16][CH:17]([CH3:18])[CH3... | CC(C)(C)OC(=O)N1CCNCC1.CC(C)Cn1nc(-c2ccc(S(C)(=O)=O)cc2)cc(COS(C)(=O)=O)c1=O.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F | Cc1c(-c2ccc(S(C)(=O)=O)cc2)nn(CC(C)C)c(=O)c1N1CCN(C(=O)OC(C)(C)C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | adbd4ad9eede124c54811c9f9237f48f5213f888183095ea7436009dbb07530e | f8979a7dc32618975f84bf1d08d0eb1a0766a30fc7e3bcdfee8ffc6d86d4188b | O=c1[nH]nc(-c2ccccc2)cc1N1CCNCC1 | C-C(-C)-C-n1:n:c(-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5]):c:c(-C-O-S(-C)(=O)=O):c:1=O.C-c1:c:c:c(-[c;H0;D3;+0:6]2:[#7;a:7]:[#7;a:8](-[C:9]):[c:10](=[O;D1;H0:11]):[c;H0;D3;+0:12](-N3-C-C-N(-C(=O)-O-C(-C)(-C)-C)-C-C-3):[c:13]:2-[C;D1;H3:14]):c:c:1-F.[#7:15]1-[C:16]-[C:17]-[NH;D2;+0:18]-[C:19]-[C:20]-1>>[C:9]-[#7;a:8]1:... | 75.9 | [{"value": 75.9, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC=C(C=C1)S(=O)(=O)C)CC(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-isobutyl-4-methanesulfonyloxymethyl-6-[4-(methylsulfonyl)phenyl]-2H-pyridazin-3-one and tert-butyl 1-piperazinecarboxylate were reacted to yield the title compound as a yellow oil (yield: 75.9%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic halide.Carbamic ester.Ether.Secondary amine.Tertiary amine.Boc | Tertiary amine | C1CNCC[NH]1.c1ccnnc1.c1ccccc1.c1ccccc1.c1ccnnc1.C1CNCCN1 | c1ccnnc1.c1ccccc1.C1C[NH]CC[NH]1 | c1ccnnc1.c1ccccc1.C1C[NH]CC[NH]1 | MsOH.HF | null | null | null | CC(C)(C)OC(=O)N1CCNCC1.CC(C)Cn1nc(-c2ccc(S(C)(=O)=O)cc2)cc(COS(C)(=O)=O)c1=O.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1c(-c2ccc(S(C)(=O)=O)cc2)nn(CC(C)C)c(=O)c1N1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b3423afc01ca486a9a249ab1a15b1858 | CC(C)Cn1nc(-c2ccc(S(C)(=O)=O)cc2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1c(-c2ccc(S(C)(=O)=O)cc2)nn(CC(C)C)c(=O)c1N1CCN(C)CC1 | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C(C(C)C)N1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC=C(C=C1)S(=O)(=O)C.CN1CCNCC1>>C(C(C)C)N1N=C(C(=C(C1=O)N1CCN(CC1)C)C)C1=CC=C(C=C1)S(=O)(=O)C | CS(=O)(=O)OC[c:22]1[cH:2][c:3](-[c:4]2[cH:5][cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][cH:13]2)[n:14][n:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[c:20]1=[O:21].[NH:23]1[CH2:24][CH2:25][N:26]([CH3:27])[CH2:28][CH2:29]1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2[CH3:1])cc1F>>[CH3:1][c:2]1[c:3](-[c:4]2[cH... | CC(C)Cn1nc(-c2ccc(S(C)(=O)=O)cc2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F | Cc1c(-c2ccc(S(C)(=O)=O)cc2)nn(CC(C)C)c(=O)c1N1CCN(C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 2a0dbc48e846de8e0c36eabe2ecaa3dda67e2c62a942dd827dcb6cda2589c033 | f8979a7dc32618975f84bf1d08d0eb1a0766a30fc7e3bcdfee8ffc6d86d4188b | O=c1[nH]nc(-c2ccccc2)cc1N1CCNCC1 | C-C(-C)-C-n1:n:c(-c2:c:c:c(-C):c(-F):c:2):c(-[CH3;D1;+0:1]):c(-N2-C-C-N(-C(=O)-O-C(-C)(-C)-C)-C-C-2):c:1=O.C-S(=O)(=O)-O-C-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[c:4](-[c:5]):[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10].[#7:11]1-[C:12]-[C:13]-[NH;D2;+0:14]-[C:15]-[C:16]-1>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:4](-[c:5]):[c;H0;D3;+0:3]... | 88.5 | [{"value": 88.5, "product": "C(C(C)C)N1N=C(C(=C(C1=O)N1CCN(CC1)C)C)C1=CC=C(C=C1)S(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-isobutyl-4-methanesulfonyloxymethyl-6-[4-(methylsulfonyl)phenyl]-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 88.5%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Aromatic halide.Carbamic ester.Ether.Secondary amine.Tertiary amine.Boc | Tertiary amine | c1ccnnc1.C1CNCC[NH]1.c1ccccc1.c1ccnnc1.C1CNCCN1 | c1ccnnc1.C1C[NH]CC[NH]1 | c1ccnnc1.c1ccccc1.C1C[NH]CC[NH]1 | MsOH.HF | null | null | null | CC(C)Cn1nc(-c2ccc(S(C)(=O)=O)cc2)cc(COS(C)(=O)=O)c1=O.CN1CCNCC1.Cc1ccc(-c2nn(CC(C)C)c(=O)c(N3CCN(C(=O)OC(C)(C)C)CC3)c2C)cc1F>>Cc1c(-c2ccc(S(C)(=O)=O)cc2)nn(CC(C)C)c(=O)c1N1CCN(C)CC1 |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-70106503310b486f9426aa13d75982e5 | BrCC1CCCC1.COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O>>COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CC2CCCC2)c1=O | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CO.FC=1C=C(C=CC1OC)C=1C=C(C(NN1)=O)C(=O)OC.C1(CCCC1)CBr>>C1(CCCC1)CN1N=C(C=C(C1=O)C(=O)OC)C1=CC(=C(C=C1)OC)F | Br[CH2:19][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([F:15])[cH:16]2)[n:17][nH:18][c:25]1=[O:26]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([F:15])[cH:16]2)[n:17][n:18]([CH2:19][C... | BrCC1CCCC1.COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CC2CCCC2)c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 456217c8bdd4490079dbc0339e1b1eedc560d0b24ec9d54c4ed1fbd8e71fb3dc | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1ccc(-c2ccccc2)nn1CC1CCCC1 | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[nH;D2;+0:11]:[#7;a:12]:[c:13]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]):[#7;a:12]:[c:13] | 72 | [{"value": 72.0, "product": "C1(CCCC1)CN1N=C(C=C(C1=O)C(=O)OC)C1=CC(=C(C=C1)OC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (6), 6-(3-fluoro-4-methoxyphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one and cyclopentylmethyl bromide {J. Org. Chem., 36, 3103 (1971)} were reacted to yield the title compound as yellow needles (yield: 72.0%).
Conditions: See reaction.notes.procedure_details.
Workup: , 36, 3103 (1971... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnncc1 | c1ccnnc1 | c1ccnnc1.c1ccccc1.C1CCCC1 | HBr | null | null | null | BrCC1CCCC1.COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O>>COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CC2CCCC2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3797b85c4944485da49699fb9a982709 | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CC2CCCC2)c1=O>>COc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CCCC3)n2)cc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.C1(CCCC1)CN1N=C(C=C(C1=O)C(=O)OC)C1=CC(=C(C=C1)OC)F>>C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CCCC1)=O | C[O:12][C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:24]([F:25])[cH:23]2)[n:22][n:15]([CH2:16][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[c:13]1=[O:14])=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13](=[O:14])[n:15]([CH2:16][CH:17]3[CH2:18][CH2:19][CH2:20]... | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CC2CCCC2)c1=O | COc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CCCC3)n2)cc1F | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccccc2)nn1CC1CCCC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 71.1 | [{"value": 71.1, "product": "C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (7), 2-cyclopentylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one was reacted to yield the title compound as a yellow powder (yield: 71.1%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccnnc1.C1CCCC1 | Other | null | null | null | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CC2CCCC2)c1=O>>COc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CCCC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-740a126536784c0ba93e047e84719970 | COc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CCCC3)n2)cc1F>>COc1ccc(-c2cc(CO)c(=O)n(CC3CCCC3)n2)cc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CN1C(C=2C(C1=O)=CC=CC2)=O.C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CCCC1)=O>>C1(CCCC1)CN1N=C(C=C(C1=O)CO)C1=CC(=C(C=C1)OC)F | O=[C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:23]([F:24])[cH:22]2)[n:21][n:14]([CH2:15][CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[c:12]1=[O:13])[OH:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][OH:11])[c:12](=[O:13])[n:14]([CH2:15][CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)[n... | COc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CCCC3)n2)cc1F | COc1ccc(-c2cc(CO)c(=O)n(CC3CCCC3)n2)cc1F | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)nn1CC1CCCC1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10]>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:9]:1=[O;D1;H0:10] | 47.3 | [{"value": 47.3, "product": "C1(CCCC1)CN1N=C(C=C(C1=O)CO)C1=CC(=C(C=C1)OC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-carboxy-2-cyclopentylmethyl-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one was reacted to yield the title compound as a yellow powder (yield: 47.3%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccnnc1.C1CCCC1 | Other | null | null | null | COc1ccc(-c2cc(C(=O)O)c(=O)n(CC3CCCC3)n2)cc1F>>COc1ccc(-c2cc(CO)c(=O)n(CC3CCCC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-14f2731ddd3b4d37959e64c1febe9385 | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CCCC3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC3CCCC3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C1(CCCC1)CN1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC(=C(C=C1)OC)F.CN1CCNCC1>>C1(CCCC1)CN1N=C(C=C(C1=O)CN1CCN(CC1)C)C1=CC(=C(C=C1)OC)F | [NH:11]1[CH2:12][CH2:13][N:14]([CH3:15])[CH2:16][CH2:17]1.CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:29]([F:30])[cH:28]2)[n:27][n:20]([CH2:21][CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)[c:18]1=[O:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][N:11]3[CH2:12][CH2:13... | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CCCC3)n2)cc1F | COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC3CCCC3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1CC1CCCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 61.4 | [{"value": 61.4, "product": "C1(CCCC1)CN1N=C(C=C(C1=O)CN1CCN(CC1)C)C1=CC(=C(C=C1)OC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-cyclopentylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 61.4%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.C1CCCC1 | MsOH.HO- | null | null | null | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CCCC3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CC3CCCC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-09757db6ecc3459884b3f63940f25133 | CNC.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CCCC3)n2)cc1F>>COc1ccc(-c2cc(CN(C)C)c(=O)n(CC3CCCC3)n2)cc1F | C1(CCCC1)CN1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC(=C(C=C1)OC)F.CNC>>C1(CCCC1)CN1N=C(C=C(C1=O)CN(C)C)C1=CC(=C(C=C1)OC)F | [NH:11]([CH3:12])[CH3:13].CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:25]([F:26])[cH:24]2)[n:23][n:16]([CH2:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[c:14]1=[O:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][N:11]([CH3:12])[CH3:13])[c:14](=[O:15])[n:16]([CH2:17... | CNC.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CCCC3)n2)cc1F | COc1ccc(-c2cc(CN(C)C)c(=O)n(CC3CCCC3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1ccc(-c2ccccc2)nn1CC1CCCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C;D1;H3:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:11](-[C;D1;H3:10])-[C;D1;H3:12]):[c:8]:1=[O;D1;H0:9] | 63.7 | [{"value": 63.7, "product": "C1(CCCC1)CN1N=C(C=C(C1=O)CN(C)C)C1=CC(=C(C=C1)OC)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 7, 2-cyclopentylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and dimethylamine were reacted to yield the title compound as a yellow oil (yield: 63.7%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccnnc1.C1CCCC1 | MsOH.HO- | null | null | null | CNC.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CCCC3)n2)cc1F>>COc1ccc(-c2cc(CN(C)C)c(=O)n(CC3CCCC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-86f3e597f9a249a098df0721367ec558 | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CCCC3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CCCC3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.C1(CCCC1)CN1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC(=C(C=C1)OC)F.N1(CCNCC1)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CCCC1)=O | [NH:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]1.CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:35]([F:36])[cH:34]2)[n:33][n:26]([CH2:27][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)[c:24]1=[O:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[... | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CCCC3)n2)cc1F | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CCCC3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1CC1CCCC1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 78.8 | [{"value": 78.8, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-cyclopentylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and tert-butyl 1-piperazinecarboxylate were reacted to yield the title compound as a yellow oil (yield: 78.8%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.C1CCCC1 | MsOH.HO- | null | null | null | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CC3CCCC3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CCCC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-29e53ed3ba274f1d9e1296751e1ed64e | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CCCC3)n2)cc1F>>COc1ccc(-c2cc(CN)c(=O)n(CC3CCCC3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CCCC1)=O.C1(CCCC1)CN1N=C(C=C(C1=O)COS(=O)(=O)C)C1=CC(=C(C=C1)OC)F>>NCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CCCC1)=O | CC(C)(C)OC(=O)N1CC[N:11]([CH2:10][c:9]2[cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[c:23]([F:24])[cH:22]3)[n:21][n:14]([CH2:15][CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)[c:12]2=[O:13])CC1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][NH2:11])[c:12](=[O:13])[n:14]([CH2:15][CH:16]3[CH2:17][CH2:18... | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CCCC3)n2)cc1F | COc1ccc(-c2cc(CN)c(=O)n(CC3CCCC3)n2)cc1F | null | null | null | Reduction | OtherReaction | 23146a52518addfb1c2672d9eda28be46306c0529900b58e4e443b48598a246d | 8db4ab69acf74a26aa2337e69e043c35d4e223d9c589e65301835fe886fa6f52 | O=c1ccc(-c2ccccc2)nn1CC1CCCC1 | C-C(-C)(-C)-O-C(=O)-N1-C-C-[N;H0;D3;+0:1](-[C:2]-[c:3]:[c:4]:[#7;a:5])-C-C-1>>[#7;a:5]:[c:4]:[c:3]-[C:2]-[NH2;D1;+0:1] | 53.7 | [{"value": 53.7, "product": "NCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1CCCC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 24 (1), 2-cyclopentylmethyl-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one was reacted to yield a crude product. Without purification, the crude product was reacted further in accordance with the procedure of Example 24 (2) to yield the title compound as a ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Tertiary amine.Boc | Primary amine | C1CNCC[NH]1 | null | c1ccccc1.c1ccnnc1.C1CCCC1 | HO- | null | null | null | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CC3CCCC3)n2)cc1F>>COc1ccc(-c2cc(CN)c(=O)n(CC3CCCC3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0297713c6c9247fcb65edc90485f6498 | COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O.Fc1ccc(CCl)cc1>>COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(F)cc2)c1=O | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CO.FC=1C=C(C=CC1OC)C=1C=C(C(NN1)=O)C(=O)OC.FC1=CC=C(CCl)C=C1>>FC1=CC=C(CN2N=C(C=C(C2=O)C(=O)OC)C2=CC(=C(C=C2)OC)F)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([F:15])[cH:16]2)[n:17][nH:18][c:27]1=[O:28].Cl[CH2:19][c:20]1[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([F:15])[cH:16]2)[n:17][n:18]([... | COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O.Fc1ccc(CCl)cc1 | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(F)cc2)c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 456217c8bdd4490079dbc0339e1b1eedc560d0b24ec9d54c4ed1fbd8e71fb3dc | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[nH;D2;+0:11]:[#7;a:12]:[c:13]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[#7;a:12]:[c:13] | 86.6 | [{"value": 86.6, "product": "FC1=CC=C(CN2N=C(C=C(C2=O)C(=O)OC)C2=CC(=C(C=C2)OC)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (6), 6-(3-fluoro-4-methoxyphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one and 4-fluorobenzyl chloride were reacted to yield the title compound as a slightly-yellow crystalline powder (yield: 86.6%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnncc1 | c1ccnnc1 | c1ccnnc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O.Fc1ccc(CCl)cc1>>COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(F)cc2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b14b2f59787d4ae3b3b8712a938b923e | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(F)cc2)c1=O>>COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.FC1=CC=C(CN2N=C(C=C(C2=O)C(=O)OC)C2=CC(=C(C=C2)OC)F)C=C1>>C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1=CC=C(C=C1)F)=O | C[O:12][C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:26]([F:27])[cH:25]2)[n:24][n:15]([CH2:16][c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]2)[c:13]1=[O:14])=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13](=[O:14])[n:15]([CH2:16][c:17]3[cH:18][cH:19][c... | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(F)cc2)c1=O | COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 97.7 | [{"value": 97.7, "product": "C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (7), 2-(4-fluorobenzyl)-6-(3-fluoro-4-methoxyphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one was reacted to yield the title compound as a yellow powder (yield: 97.7%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(F)cc2)c1=O>>COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(F)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-04bfd972c53743899c8054411c2f57b0 | COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CO)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CN1C(C=2C(C1=O)=CC=CC2)=O.C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1=CC=C(C=C1)F)=O>>FC1=CC=C(CN2N=C(C=C(C2=O)CO)C2=CC(=C(C=C2)OC)F)C=C1 | O=[C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:25]([F:26])[cH:24]2)[n:23][n:14]([CH2:15][c:16]2[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]2)[c:12]1=[O:13])[OH:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][OH:11])[c:12](=[O:13])[n:14]([CH2:15][c:16]3[cH:17][cH:18][c:19]([F:20])... | COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | COc1ccc(-c2cc(CO)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10]>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:9]:1=[O;D1;H0:10] | 27 | [{"value": 27.0, "product": "FC1=CC=C(CN2N=C(C=C(C2=O)CO)C2=CC(=C(C=C2)OC)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-carboxy-2-(4-fluorobenzyl)-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one was reacted to yield the title compound as a yellow powder (yield: 27.0%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | Other | null | null | null | COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CO)c(=O)n(Cc3ccc(F)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-8dd2fb9aa1e841e48cab5069dfd000bc | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.FC1=CC=C(CN2N=C(C=C(C2=O)COS(=O)(=O)C)C2=CC(=C(C=C2)OC)F)C=C1.CN1CCNCC1>>FC1=CC=C(CN2N=C(C=C(C2=O)CN2CCN(CC2)C)C2=CC(=C(C=C2)OC)F)C=C1 | [NH:11]1[CH2:12][CH2:13][N:14]([CH3:15])[CH2:16][CH2:17]1.CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:31]([F:32])[cH:30]2)[n:29][n:20]([CH2:21][c:22]2[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]2)[c:18]1=[O:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][N:11]3[CH2:1... | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1Cc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 45.8 | [{"value": 45.8, "product": "FC1=CC=C(CN2N=C(C=C(C2=O)CN2CCN(CC2)C)C2=CC(=C(C=C2)OC)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-(4-fluorobenzyl)-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and 1-methylpiprazine were reacted to yield the title compound as a slightly-brown crystalline powder (yield: 45.8%).
Conditions: See reaction.notes.procedure_details.
Workup: were re... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.c1ccccc1 | MsOH.HO- | null | null | null | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(Cc3ccc(F)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-bee39e7f05844292ae39bee8e9a5d235 | CNC.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CN(C)C)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | FC1=CC=C(CN2N=C(C=C(C2=O)COS(=O)(=O)C)C2=CC(=C(C=C2)OC)F)C=C1.CNC>>CN(C)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1=CC=C(C=C1)F)=O | [NH:11]([CH3:12])[CH3:13].CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:27]([F:28])[cH:26]2)[n:25][n:16]([CH2:17][c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]2)[c:14]1=[O:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][N:11]([CH3:12])[CH3:13])[c:14](=[O:15])[n:16... | CNC.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | COc1ccc(-c2cc(CN(C)C)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C;D1;H3:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:11](-[C;D1;H3:10])-[C;D1;H3:12]):[c:8]:1=[O;D1;H0:9] | 60.8 | [{"value": 60.8, "product": "CN(C)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 7, 2-(4-fluorobenzyl)-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and dimethylamine were reacted to yield the title compound as a slightly-yellow crystalline powder (yield: 60.8%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | MsOH.HO- | null | null | null | CNC.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CN(C)C)c(=O)n(Cc3ccc(F)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-a23edce8748b4bc897de7e1e64fc60ca | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.FC1=CC=C(CN2N=C(C=C(C2=O)COS(=O)(=O)C)C2=CC(=C(C=C2)OC)F)C=C1.N1(CCNCC1)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1=CC=C(C=C1)F)=O | [NH:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]1.CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:37]([F:38])[cH:36]2)[n:35][n:26]([CH2:27][c:28]2[cH:29][cH:30][c:31]([F:32])[cH:33][cH:34]2)[c:24]1=[O:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5... | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1Cc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 78.8 | [{"value": 78.8, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-(4-fluorobenzyl)-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and tert-butyl 1-piperazinecarboxylate were reacted to yield the title compound as a yellow oil (yield: 78.8%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.c1ccccc1 | MsOH.HO- | null | null | null | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(Cc3ccc(F)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-f9edb749026f4a45b2f9abb04991d1b4 | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(Cc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CN)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1=CC=C(C=C1)F)=O.FC1=CC=C(CN2N=C(C=C(C2=O)COS(=O)(=O)C)C2=CC(=C(C=C2)OC)F)C=C1>>NCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1=CC=C(C=C1)F)=O | CC(C)(C)OC(=O)N1CC[N:11]([CH2:10][c:9]2[cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[c:25]([F:26])[cH:24]3)[n:23][n:14]([CH2:15][c:16]3[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]3)[c:12]2=[O:13])CC1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][NH2:11])[c:12](=[O:13])[n:14]([CH2:15][c:16]3[cH:17]... | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | COc1ccc(-c2cc(CN)c(=O)n(Cc3ccc(F)cc3)n2)cc1F | null | null | null | Reduction | OtherReaction | 23146a52518addfb1c2672d9eda28be46306c0529900b58e4e443b48598a246d | 8db4ab69acf74a26aa2337e69e043c35d4e223d9c589e65301835fe886fa6f52 | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | C-C(-C)(-C)-O-C(=O)-N1-C-C-[N;H0;D3;+0:1](-[C:2]-[c:3]:[c:4]:[#7;a:5])-C-C-1>>[#7;a:5]:[c:4]:[c:3]-[C:2]-[NH2;D1;+0:1] | 50.4 | [{"value": 50.4, "product": "NCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 24 (1), 2-(4-fluorobenzyl)-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one was reacted to yield a crude product. Without purification, the crude product was reacted further in accordance with the procedure of Example 24 (2) to yield the title compound as a p... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Tertiary amine.Boc | Primary amine | C1CNCC[NH]1 | null | c1ccccc1.c1ccnnc1.c1ccccc1 | HO- | null | null | null | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(Cc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CN)c(=O)n(Cc3ccc(F)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-9757eb78aaf243dd8b7402bab0cddbc6 | COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O.OCCCc1ccc(F)cc1>>COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CCCc2ccc(F)cc2)c1=O | FC1=CC=C(C=C1)CCCO.FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CO.FC=1C=C(C=CC1OC)C=1C=C(C(NN1)=O)C(=O)OC.S(C)(=O)(=O)[O-]>>FC=1C=C(C=CC1OC)C=1C=C(C(N(N1)CCCC1=CC=C(C=C1)F)=O)C(=O)OC | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([F:15])[cH:16]2)[n:17][nH:18][c:29]1=[O:30].O[CH2:19][CH2:20][CH2:21][c:22]1[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([F:15])[cH:16]2... | COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O.OCCCc1ccc(F)cc1 | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CCCc2ccc(F)cc2)c1=O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | b95c29713c24b74adbff47a799682c402f410a17712dc002150c13b278d09bba | 2ab4024aa17b6e89368e6fe8ee731d32c7611cb9b23de403e301e8362fea90b1 | O=c1ccc(-c2ccccc2)nn1CCCc1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](=[O;D1;H0:9]):[nH;D2;+0:10]:[#7;a:11]:[c:12]>>[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](=[O;D1;H0:9]):[n;H0;D3;+0:10](-[CH2;D2;+0:1]-[C:2]-[C:3]):[#7;a:11]:[c:12] | 90.1 | [{"value": 90.1, "product": "FC=1C=C(C=CC1OC)C=1C=C(C(N(N1)CCCC1=CC=C(C=C1)F)=O)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (6), 6-(3-fluoro-4-methoxyphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one and the mesylate derivative of 3-(4-fluorophenyl)-1-propanol {J. Med. Chem., 19, 461 (1976)} were reacted to yield the title compound as a yellow oil (yield: 90.1%). The mesylate derivative was prepared in accord... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | null | c1cnncc1 | c1ccnnc1 | c1ccnnc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O.OCCCc1ccc(F)cc1>>COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CCCc2ccc(F)cc2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-72d462986a3041f7b6769f8b11c4c5ad | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CCCc2ccc(F)cc2)c1=O>>COc1ccc(-c2cc(C(=O)O)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.FC=1C=C(C=CC1OC)C=1C=C(C(N(N1)CCCC1=CC=C(C=C1)F)=O)C(=O)OC>>C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CCCC1=CC=C(C=C1)F)=O | C[O:12][C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:28]([F:29])[cH:27]2)[n:26][n:15]([CH2:16][CH2:17][CH2:18][c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[c:13]1=[O:14])=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13](=[O:14])[n:15]([CH2:16][CH2:17... | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CCCc2ccc(F)cc2)c1=O | COc1ccc(-c2cc(C(=O)O)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccccc2)nn1CCCc1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 89.2 | [{"value": 89.2, "product": "C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CCCC1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (7), 6-(3-fluoro-4-methoxyphenyl)-2-[3-(4-fluorophenyl)propyl]-4-methoxycarbonyl-2H-pyridazin-3-one was reacted to yield the title compound as a yellow powder (yield: 89.2%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(CCCc2ccc(F)cc2)c1=O>>COc1ccc(-c2cc(C(=O)O)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-b0d283c8f3cd40afb9343776db9308af | COc1ccc(-c2cc(C(=O)O)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CO)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CN1C(C=2C(C1=O)=CC=CC2)=O.C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CCCC1=CC=C(C=C1)F)=O>>FC=1C=C(C=CC1OC)C=1C=C(C(N(N1)CCCC1=CC=C(C=C1)F)=O)CO | O=[C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:27]([F:28])[cH:26]2)[n:25][n:14]([CH2:15][CH2:16][CH2:17][c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]2)[c:12]1=[O:13])[OH:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][OH:11])[c:12](=[O:13])[n:14]([CH2:15][CH2:16][CH2:17][c:... | COc1ccc(-c2cc(C(=O)O)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | COc1ccc(-c2cc(CO)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)nn1CCCc1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10]>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:9]:1=[O;D1;H0:10] | 37 | [{"value": 37.0, "product": "FC=1C=C(C=CC1OC)C=1C=C(C(N(N1)CCCC1=CC=C(C=C1)F)=O)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-carboxy-6-(3-fluoro-4-methoxyphenyl)-2-[3-(4-fluorophenyl)propyl]-2H-pyridazin-3-one was reacted to yield the title compound as a yellow powder (yield: 37.0%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | Other | null | null | null | COc1ccc(-c2cc(C(=O)O)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CO)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-969a2ac2825a41809089de33e44a9c98 | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.FC=1C=C(C=CC1OC)C=1C=C(C(N(N1)CCCC1=CC=C(C=C1)F)=O)COS(=O)(=O)C.CN1CCNCC1>>FC=1C=C(C=CC1OC)C=1C=C(C(N(N1)CCCC1=CC=C(C=C1)F)=O)CN1CCN(CC1)C | [NH:11]1[CH2:12][CH2:13][N:14]([CH3:15])[CH2:16][CH2:17]1.CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:33]([F:34])[cH:32]2)[n:31][n:20]([CH2:21][CH2:22][CH2:23][c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[c:18]1=[O:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:... | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1CCCc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 79.3 | [{"value": 79.3, "product": "FC=1C=C(C=CC1OC)C=1C=C(C(N(N1)CCCC1=CC=C(C=C1)F)=O)CN1CCN(CC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 6-(3-fluoro-4-methoxyphenyl)-2-[3-(4-fluorophenyl)propyl]-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as a yellow oil (yield: 79.3%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.c1ccccc1 | MsOH.HO- | null | null | null | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-e10a6d32b3d740e695807ccc89fba89b | CNC.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CN(C)C)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | FC=1C=C(C=CC1OC)C=1C=C(C(N(N1)CCCC1=CC=C(C=C1)F)=O)COS(=O)(=O)C.CNC>>CN(C)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CCCC1=CC=C(C=C1)F)=O | [NH:11]([CH3:12])[CH3:13].CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:29]([F:30])[cH:28]2)[n:27][n:16]([CH2:17][CH2:18][CH2:19][c:20]2[cH:21][cH:22][c:23]([F:24])[cH:25][cH:26]2)[c:14]1=[O:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][N:11]([CH3:12])[CH3:13])[c:1... | CNC.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | COc1ccc(-c2cc(CN(C)C)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1ccc(-c2ccccc2)nn1CCCc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C;D1;H3:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:11](-[C;D1;H3:10])-[C;D1;H3:12]):[c:8]:1=[O;D1;H0:9] | 61.8 | [{"value": 61.8, "product": "CN(C)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CCCC1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 7, 6-(3-fluoro-4-methoxyphenyl)-2-[3-(4-fluorophenyl)propyl]-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and dimethylamine were reacted to yield the title compound as a pale yellow crystalline powder (yield: 61.8%).
Conditions: See reaction.notes.procedure_details.
Workup: were reac... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | MsOH.HO- | null | null | null | CNC.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CN(C)C)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-3558371fc3634f03a9a37eba55d9bdae | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.FC=1C=C(C=CC1OC)C=1C=C(C(N(N1)CCCC1=CC=C(C=C1)F)=O)COS(=O)(=O)C.N1(CCNCC1)C(=O)OC(C)(C)C>>C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CCCC1=CC=C(C=C1)F)=O | [NH:11]1[CH2:12][CH2:13][N:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:22][CH2:23]1.CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:39]([F:40])[cH:38]2)[n:37][n:26]([CH2:27][CH2:28][CH2:29][c:30]2[cH:31][cH:32][c:33]([F:34])[cH:35][cH:36]2)[c:24]1=[O:25]>>[CH3:1][O:2][... | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1CCCc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 72.6 | [{"value": 72.6, "product": "C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CCCC1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 6-(3-fluoro-4-methoxyphenyl)-2-[3-(4-fluorophenyl)propyl]-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and tert-butyl 1-piperazinecarboxylate were reacted to yield the title compound as a yellow oil (yield: 72.6%).
Conditions: See reaction.notes.procedure_details.
Workup: wer... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.c1ccccc1 | MsOH.HO- | null | null | null | CC(C)(C)OC(=O)N1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-6c2a06e8771b47df9c4944efecfcbe1f | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CN)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)CC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CCCC1=CC=C(C=C1)F)=O.FC=1C=C(C=CC1OC)C=1C=C(C(N(N1)CCCC1=CC=C(C=C1)F)=O)COS(=O)(=O)C>>NCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CCCC1=CC=C(C=C1)F)=O | CC(C)(C)OC(=O)N1CC[N:11]([CH2:10][c:9]2[cH:8][c:7](-[c:6]3[cH:5][cH:4][c:3]([O:2][CH3:1])[c:27]([F:28])[cH:26]3)[n:25][n:14]([CH2:15][CH2:16][CH2:17][c:18]3[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]3)[c:12]2=[O:13])CC1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][NH2:11])[c:12](=[O:13])[n:14]([CH2:1... | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | COc1ccc(-c2cc(CN)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F | null | null | null | Reduction | OtherReaction | 23146a52518addfb1c2672d9eda28be46306c0529900b58e4e443b48598a246d | 8db4ab69acf74a26aa2337e69e043c35d4e223d9c589e65301835fe886fa6f52 | O=c1ccc(-c2ccccc2)nn1CCCc1ccccc1 | C-C(-C)(-C)-O-C(=O)-N1-C-C-[N;H0;D3;+0:1](-[C:2]-[c:3]:[c:4]:[#7;a:5])-C-C-1>>[#7;a:5]:[c:4]:[c:3]-[C:2]-[NH2;D1;+0:1] | 41.7 | [{"value": 41.7, "product": "NCC=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CCCC1=CC=C(C=C1)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 24 (1), 6-(3-fluoro-4-methoxyphenyl)-2-[3-(4-fluorophenyl)propyl]-4-methanesulfonyloxymethyl-2H-pyridazin-3-one was reacted to a crude product. Without purification, the crude product was reacted in accordance with the procedure of Example 24 (2) to yield the title compound as a pale ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Tertiary amine.Boc | Primary amine | C1CNCC[NH]1 | null | c1ccccc1.c1ccnnc1.c1ccccc1 | HO- | null | null | null | COc1ccc(-c2cc(CN3CCN(C(=O)OC(C)(C)C)CC3)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F>>COc1ccc(-c2cc(CN)c(=O)n(CCCc3ccc(F)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-245d1a78a11e4d2bb32782f1a00fda24 | COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O.ClCc1ccc(Cl)cc1>>COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(Cl)cc2)c1=O | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CO.FC=1C=C(C=CC1OC)C=1C=C(C(NN1)=O)C(=O)OC.ClC1=CC=C(CCl)C=C1>>ClC1=CC=C(CN2N=C(C=C(C2=O)C(=O)OC)C2=CC(=C(C=C2)OC)F)C=C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([F:15])[cH:16]2)[n:17][nH:18][c:27]1=[O:28].Cl[CH2:19][c:20]1[cH:21][cH:22][c:23]([Cl:24])[cH:25][cH:26]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([F:15])[cH:16]2)[n:17][n:18](... | COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O.ClCc1ccc(Cl)cc1 | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(Cl)cc2)c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 456217c8bdd4490079dbc0339e1b1eedc560d0b24ec9d54c4ed1fbd8e71fb3dc | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[nH;D2;+0:11]:[#7;a:12]:[c:13]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[#7;a:12]:[c:13] | 97.6 | [{"value": 97.6, "product": "ClC1=CC=C(CN2N=C(C=C(C2=O)C(=O)OC)C2=CC(=C(C=C2)OC)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (6), 6-(3-fluoro-4-methoxyphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one and 4-chlorobenzyl chloride were reacted to yield the title compound as yellow needles (yield: 97.6%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnncc1 | c1ccnnc1 | c1ccnnc1.c1ccccc1.c1ccccc1 | HCl | null | null | null | COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O.ClCc1ccc(Cl)cc1>>COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(Cl)cc2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d6d1219af12d4e5e8426d879ab02395b | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(Cl)cc2)c1=O>>COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.ClC1=CC=C(CN2N=C(C=C(C2=O)C(=O)OC)C2=CC(=C(C=C2)OC)F)C=C1>>C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1=CC=C(C=C1)Cl)=O | C[O:12][C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:26]([F:27])[cH:25]2)[n:24][n:15]([CH2:16][c:17]2[cH:18][cH:19][c:20]([Cl:21])[cH:22][cH:23]2)[c:13]1=[O:14])=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13](=[O:14])[n:15]([CH2:16][c:17]3[cH:18][cH:19][... | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(Cl)cc2)c1=O | COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 96 | [{"value": 96.0, "product": "C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1=CC=C(C=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (7), 2-(4-chlorobenzyl)-6-(3-fluoro-4-methoxyphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one was reacted to yield the title compound as a pale yellow crystalline powder (yield: 96.0%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(Cl)cc2)c1=O>>COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-0c0f454ff7734536a2500814511e1c41 | COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F>>COc1ccc(-c2cc(CO)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CN1C(C=2C(C1=O)=CC=CC2)=O.C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1=CC=C(C=C1)Cl)=O>>ClC1=CC=C(CN2N=C(C=C(C2=O)CO)C2=CC(=C(C=C2)OC)F)C=C1 | O=[C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:25]([F:26])[cH:24]2)[n:23][n:14]([CH2:15][c:16]2[cH:17][cH:18][c:19]([Cl:20])[cH:21][cH:22]2)[c:12]1=[O:13])[OH:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][OH:11])[c:12](=[O:13])[n:14]([CH2:15][c:16]3[cH:17][cH:18][c:19]([Cl:20... | COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F | COc1ccc(-c2cc(CO)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10]>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:9]:1=[O;D1;H0:10] | 20.4 | [{"value": 20.4, "product": "ClC1=CC=C(CN2N=C(C=C(C2=O)CO)C2=CC(=C(C=C2)OC)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-carboxy-2-(4-chlorobenzyl)-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one was reacted to yield the title compound as pale yellow needles (yield: 20.4%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | Other | null | null | null | COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F>>COc1ccc(-c2cc(CO)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-d5fb31144de2413288f9f37a104ef2de | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.ClC1=CC=C(CN2N=C(C=C(C2=O)COS(=O)(=O)C)C2=CC(=C(C=C2)OC)F)C=C1.CN1CCNCC1>>ClC1=CC=C(CN2N=C(C=C(C2=O)CN2CCN(CC2)C)C2=CC(=C(C=C2)OC)F)C=C1 | [NH:11]1[CH2:12][CH2:13][N:14]([CH3:15])[CH2:16][CH2:17]1.CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:31]([F:32])[cH:30]2)[n:29][n:20]([CH2:21][c:22]2[cH:23][cH:24][c:25]([Cl:26])[cH:27][cH:28]2)[c:18]1=[O:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][N:11]3[CH2:... | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F | COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1Cc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 39.5 | [{"value": 39.5, "product": "ClC1=CC=C(CN2N=C(C=C(C2=O)CN2CCN(CC2)C)C2=CC(=C(C=C2)OC)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-(4-chlorobenzyl)-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as pale brown prisms (yield: 39.5%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.c1ccccc1 | MsOH.HO- | null | null | null | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-303e0dc0019f4156bc6e0cf54cf69910 | CNC.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F>>COc1ccc(-c2cc(CN(C)C)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F | ClC1=CC=C(CN2N=C(C=C(C2=O)COS(=O)(=O)C)C2=CC(=C(C=C2)OC)F)C=C1.CNC>>ClC1=CC=C(CN2N=C(C=C(C2=O)CN(C)C)C2=CC(=C(C=C2)OC)F)C=C1 | [NH:11]([CH3:12])[CH3:13].CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:27]([F:28])[cH:26]2)[n:25][n:16]([CH2:17][c:18]2[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]2)[c:14]1=[O:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][N:11]([CH3:12])[CH3:13])[c:14](=[O:15])[n:1... | CNC.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F | COc1ccc(-c2cc(CN(C)C)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C;D1;H3:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:11](-[C;D1;H3:10])-[C;D1;H3:12]):[c:8]:1=[O;D1;H0:9] | 74.7 | [{"value": 74.7, "product": "ClC1=CC=C(CN2N=C(C=C(C2=O)CN(C)C)C2=CC(=C(C=C2)OC)F)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 7, 2-(4-chlorobenzyl)-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and dimethylamine were reacted to yield the title compound as a slightly-yellow crystalline powder (yield: 74.7%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | MsOH.HO- | null | null | null | CNC.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F>>COc1ccc(-c2cc(CN(C)C)c(=O)n(Cc3ccc(Cl)cc3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-7fbe98d2d8c545b9967357d14a5f9904 | COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O.Fc1ccc(CBr)cc1F>>COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(F)c(F)c2)c1=O | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CO.FC=1C=C(C=CC1OC)C=1C=C(C(NN1)=O)C(=O)OC.FC=1C=C(CBr)C=CC1F>>FC=1C=C(CN2N=C(C=C(C2=O)C(=O)OC)C2=CC(=C(C=C2)OC)F)C=CC1F | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([F:15])[cH:16]2)[n:17][nH:18][c:28]1=[O:29].Br[CH2:19][c:20]1[cH:21][cH:22][c:23]([F:24])[c:25]([F:26])[cH:27]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([O:12][CH3:13])[c:14]([F:15])[cH:16]2)[n:17][... | COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O.Fc1ccc(CBr)cc1F | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(F)c(F)c2)c1=O | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 456217c8bdd4490079dbc0339e1b1eedc560d0b24ec9d54c4ed1fbd8e71fb3dc | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[nH;D2;+0:11]:[#7;a:12]:[c:13]>>[#8:5]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9](=[O;D1;H0:10]):[n;H0;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]):[#7;a:12]:[c:13] | 92.1 | [{"value": 92.1, "product": "FC=1C=C(CN2N=C(C=C(C2=O)C(=O)OC)C2=CC(=C(C=C2)OC)F)C=CC1F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (6), 6-(3-fluoro-4-methoxyphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one and 3,4-difluorobenzyl bromide were reacted to yield the title compound as a yellow crystalline powder (yield: 92.1%)
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1cnncc1 | c1ccnnc1 | c1ccnnc1.c1ccccc1.c1ccccc1 | HBr | null | null | null | COC(=O)c1cc(-c2ccc(OC)c(F)c2)n[nH]c1=O.Fc1ccc(CBr)cc1F>>COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(F)c(F)c2)c1=O |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-fd0da7479f3c4910bc9f48780c1874b2 | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(F)c(F)c2)c1=O>>COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)COS(=O)(=O)C.FC=1C=C(CN2N=C(C=C(C2=O)C(=O)OC)C2=CC(=C(C=C2)OC)F)C=CC1F>>C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1=CC(=C(C=C1)F)F)=O | C[O:12][C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:27]([F:28])[cH:26]2)[n:25][n:15]([CH2:16][c:17]2[cH:18][cH:19][c:20]([F:21])[c:22]([F:23])[cH:24]2)[c:13]1=[O:14])=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([C:10](=[O:11])[OH:12])[c:13](=[O:14])[n:15]([CH2:16][c:17]3[cH:18][c... | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(F)c(F)c2)c1=O | COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F | null | null | null | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 97.6 | [{"value": 97.6, "product": "C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1=CC(=C(C=C1)F)F)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (7), 2-(3,4-difluorobenzyl)-6-(3-fluoro-4-methoxyphenyl)-4-methoxycarbonyl-2H-pyridazin-3-one was reacted to yield the title compound as a yellow crystalline powder (yield: 97.6%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(-c2ccc(OC)c(F)c2)nn(Cc2ccc(F)c(F)c2)c1=O>>COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-c222847b90d34f32a09c7626c75e0038 | COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F>>COc1ccc(-c2cc(CO)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F | FC1=C(C=CC(=C1)F)C=1C=C(C(N(N1)CC(C)C)=O)CN1C(C=2C(C1=O)=CC=CC2)=O.C(=O)(O)C=1C(N(N=C(C1)C1=CC(=C(C=C1)OC)F)CC1=CC(=C(C=C1)F)F)=O>>FC=1C=C(CN2N=C(C=C(C2=O)CO)C2=CC(=C(C=C2)OC)F)C=CC1F | O=[C:10]([c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:26]([F:27])[cH:25]2)[n:24][n:14]([CH2:15][c:16]2[cH:17][cH:18][c:19]([F:20])[c:21]([F:22])[cH:23]2)[c:12]1=[O:13])[OH:11]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][OH:11])[c:12](=[O:13])[n:14]([CH2:15][c:16]3[cH:17][cH:18][c:19](... | COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F | COc1ccc(-c2cc(CO)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F | null | null | null | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[c:4]:[c:5]:[#7;a:6]:[#7;a:7](-[C:8]):[c:9]:1=[O;D1;H0:10]>>[C:8]-[#7;a:7]1:[#7;a:6]:[c:5]:[c:4]:[c:3](-[CH2;D2;+0:1]-[O;D1;H1:2]):[c:9]:1=[O;D1;H0:10] | 7.7 | [{"value": 7.7, "product": "FC=1C=C(CN2N=C(C=C(C2=O)CO)C2=CC(=C(C=C2)OC)F)C=CC1F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (8), 4-carboxy-2-(3,4-difluorobenzyl)-6-(3-fluoro-4-methoxyphenyl)-2H-pyridazin-3-one was reacted to yield the title compound as slightly-yellow neeldes (yield: 7.7%).
Conditions: See reaction.notes.procedure_details.
Workup: was reacted | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | Other | null | null | null | COc1ccc(-c2cc(C(=O)O)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F>>COc1ccc(-c2cc(CO)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-baf3a5ad49e947c4b1b86a6a9af2c485 | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F | C(C)(C)(C)OC(=O)N1CCN(CC1)C=1C(N(N=C(C1C)C1=CC(=C(C=C1)C)F)CC(C)C)=O.FC=1C=C(CN2N=C(C=C(C2=O)COS(=O)(=O)C)C2=CC(=C(C=C2)OC)F)C=CC1F.CN1CCNCC1>>FC=1C=C(CN2N=C(C=C(C2=O)CN2CCN(CC2)C)C2=CC(=C(C=C2)OC)F)C=CC1F | [NH:11]1[CH2:12][CH2:13][N:14]([CH3:15])[CH2:16][CH2:17]1.CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:32]([F:33])[cH:31]2)[n:30][n:20]([CH2:21][c:22]2[cH:23][cH:24][c:25]([F:26])[c:27]([F:28])[cH:29]2)[c:18]1=[O:19]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][N:11]... | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F | COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | bc40e881c80f733cc18ae6a4c32c0d2e3ac9ce7b07d3a2cb609684e869dc6007 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1c(CN2CCNCC2)cc(-c2ccccc2)nn1Cc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[#7:10]1-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-1>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:13]2-[C:12]-[C:11]-[#7:10]-[C:15]-[C:14]-2):[c:8]:1=[O;D1;H0:9] | 55 | [{"value": 55.0, "product": "FC=1C=C(CN2N=C(C=C(C2=O)CN2CCN(CC2)C)C2=CC(=C(C=C2)OC)F)C=CC1F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 1 (10), 2-(3,4-difluorobenzyl)-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and 1-methylpiperazine were reacted to yield the title compound as slightly-yellow neeldes (yield: 55.0%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | c1ccccc1.c1ccnnc1.C1C[NH]CC[NH]1.c1ccccc1 | MsOH.HO- | null | null | null | CN1CCNCC1.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F>>COc1ccc(-c2cc(CN3CCN(C)CC3)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F |
ord_dataset-0387783899c642a8b7eb4ba379bcdf5d | ord-219d580ddc064d6bb4eb4be881f5728d | CNC.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F>>COc1ccc(-c2cc(CN(C)C)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F | FC=1C=C(CN2N=C(C=C(C2=O)COS(=O)(=O)C)C2=CC(=C(C=C2)OC)F)C=CC1F.CNC>>FC=1C=C(CN2N=C(C=C(C2=O)CN(C)C)C2=CC(=C(C=C2)OC)F)C=CC1F | [NH:11]([CH3:12])[CH3:13].CS(=O)(=O)O[CH2:10][c:9]1[cH:8][c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:28]([F:29])[cH:27]2)[n:26][n:16]([CH2:17][c:18]2[cH:19][cH:20][c:21]([F:22])[c:23]([F:24])[cH:25]2)[c:14]1=[O:15]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][c:9]([CH2:10][N:11]([CH3:12])[CH3:13])[c:14](=[O:15... | CNC.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F | COc1ccc(-c2cc(CN(C)C)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F | null | null | null | Heteroatom Alkylation and Arylation | Alkylation of amines | ba24696731c43f94422863463da0ee528bfb8ec715fd228fe0a6c2ae67b49c25 | 35d789812c3241c3a185d06663a309d930259e30563212f3884ef74718436cbc | O=c1ccc(-c2ccccc2)nn1Cc1ccccc1 | C-S(=O)(=O)-O-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[#7;a:6](-[C:7]):[c:8]:1=[O;D1;H0:9].[C;D1;H3:10]-[NH;D2;+0:11]-[C;D1;H3:12]>>[C:7]-[#7;a:6]1:[#7;a:5]:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[N;H0;D3;+0:11](-[C;D1;H3:10])-[C;D1;H3:12]):[c:8]:1=[O;D1;H0:9] | 77.1 | [{"value": 77.1, "product": "FC=1C=C(CN2N=C(C=C(C2=O)CN(C)C)C2=CC(=C(C=C2)OC)F)C=CC1F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Following the procedure of Example 7, 2-(3, 4-difluorobenzyl)-6-(3-fluoro-4-methoxyphenyl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one and dimethylamine were reacted to yield the title compound as slightly-yellow needles (yield: 77.1%).
Conditions: See reaction.notes.procedure_details.
Workup: were reacted | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Secondary amine | Tertiary amine | null | null | c1ccccc1.c1ccnnc1.c1ccccc1 | MsOH.HO- | null | null | null | CNC.COc1ccc(-c2cc(COS(C)(=O)=O)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F>>COc1ccc(-c2cc(CN(C)C)c(=O)n(Cc3ccc(F)c(F)c3)n2)cc1F |
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