dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f03ed9c7507f4091b2c9ef9cde7be8c9 | COc1ccc(-c2ncn(CCC(C)(C)NCC(O)c3ccc(OCc4ccccc4)c(CO)c3)n2)cc1>>COc1ccc(-c2ncn(CCC(C)(C)NCC(O)c3ccc(O)c(CO)c3)n2)cc1 | C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C(CNC(CCN1N=C(N=C1)C1=CC=C(C=C1)OC)(C)C)O)CO>>OC(CNC(CCN1N=C(N=C1)C1=CC=C(C=C1)OC)(C)C)C1=CC(=C(C=C1)O)CO | c1ccc(C[O:24][c:23]2[cH:22][cH:21][c:20]([CH:18]([CH2:17][NH:16][C:13]([CH2:12][CH2:11][n:10]3[cH:9][n:8][c:7](-[c:6]4[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:31][cH:30]4)[n:29]3)([CH3:14])[CH3:15])[OH:19])[cH:28][c:25]2[CH2:26][OH:27])cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[n:8][cH:9][n:10]([CH2:11][CH2:12][C:13]([... | COc1ccc(-c2ncn(CCC(C)(C)NCC(O)c3ccc(OCc4ccccc4)c(CO)c3)n2)cc1 | COc1ccc(-c2ncn(CCC(C)(C)NCC(O)c3ccc(O)c(CO)c3)n2)cc1 | null | [Pd] | O1CCCC1.CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(CCNCCCn2cnc(-c3ccccc3)n2)cc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | null | null | 3.8 g of 1-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-{3-[3-(4-methoxy-phenyl)-[1,2,4]triazol-1-yl]-1,1-dimethyl-propylamino}-ethanol are hydrogenated with 0.6 g of palladium on charcoal (5%) as catalyst in 75 mL methanol and 75 mL tetrahydrofuran. Then the catalyst is suction filtered and the filtrate is evaporated down. ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1nnc[nH]1.c1ccccc1 | Other | [Pd].O1CCCC1.CO | null | null | COc1ccc(-c2ncn(CCC(C)(C)NCC(O)c3ccc(OCc4ccccc4)c(CO)c3)n2)cc1>[Pd].O1CCCC1.CO>COc1ccc(-c2ncn(CCC(C)(C)NCC(O)c3ccc(O)c(CO)c3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e9eb6ee0f02c4baba66eefb6b40f809a | CC(C)(N)CCn1cncn1.CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1>>COC(=O)c1cc(C(O)CNC(C)(C)CCn2cncn2)ccc1OCc1ccccc1 | C(C(=O)O)(=O)O.C(C1=CC=CC=C1)OC1=C(C(=O)OC)C=C(C=C1)C(C(O)OCC)=O.CC(CCN1N=CN=C1)(C)N>>C(C1=CC=CC=C1)OC1=C(C(=O)OC)C=C(C=C1)C(CNC(CCN1N=CN=C1)(C)C)O | [NH2:11][C:12]([CH3:13])([CH3:14])[CH2:15][CH2:16][n:17]1[cH:18][n:19][cH:20][n:21]1.CCO[CH:10](O)[C:8]([c:7]1[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:24]([O:25][CH2:26][c:27]2[cH:28][cH:29][cH:30][cH:31][cH:32]2)[cH:23][cH:22]1)=[O:9]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([CH:8]([OH:9])[CH2:10][NH:11][C:12]([CH3... | CC(C)(N)CCn1cncn1.CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1 | COC(=O)c1cc(C(O)CNC(C)(C)CCn2cncn2)ccc1OCc1ccccc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 1fdebd18d8e186352a5054d1639a246066c291a759c2941bdb27defc05ab0b96 | 270f718637e505454980bf4a24a04f3a3a166f4d4160855797b4e1923ac25b66 | c1ccc(COc2ccc(CCNCCCn3cncn3)cc2)cc1 | C-C-O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4](:[c:5]):[c:6].[C:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[NH2;D1;+0:11]>>[C:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[NH;D2;+0:11]-[CH2;D2;+0:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | 9.5 g of methyl 2-benzyloxy-5-(2-ethoxy-2-hydroxy-acetyl)-benzoate and 3.1 g of 1,1-dimethyl-3-[1,2,4]triazol-1-yl-propylamine are reacted and worked up analogously to the method described for Example 2a. The crude product is dissolved in 100 mL 95% ethanol and combined with an ethanolic solution of 1.8 g of oxalic aci... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Secondary alcohol.Primary amine | Secondary alcohol.Secondary amine | null | null | c1ccccc1.c1nc[nH]n1.c1ccccc1 | HO- | C(C)O | null | null | CC(C)(N)CCn1cncn1.CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1>C(C)O>COC(=O)c1cc(C(O)CNC(C)(C)CCn2cncn2)ccc1OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6a530b77776841f8a59965f50e2d8619 | COC(=O)c1cc(C(O)CNC(C)(C)CCn2cncn2)ccc1OCc1ccccc1>>CC(C)(CCn1cncn1)NCC(O)c1ccc(OCc2ccccc2)c(CO)c1 | C(C1=CC=CC=C1)OC1=C(C(=O)OC)C=C(C=C1)C(CNC(CCN1N=CN=C1)(C)C)O.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C(CNC(CCN1N=CN=C1)(C)C)O)CO | CO[C:28]([c:27]1[c:18]([O:19][CH2:20][c:21]2[cH:22][cH:23][cH:24][cH:25][cH:26]2)[cH:17][cH:16][c:15]([CH:13]([CH2:12][NH:11][C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][n:6]2[cH:7][n:8][cH:9][n:10]2)[OH:14])[cH:30]1)=[O:29]>>[CH3:1][C:2]([CH3:3])([CH2:4][CH2:5][n:6]1[cH:7][n:8][cH:9][n:10]1)[NH:11][CH2:12][CH:13]([OH:14])[c:... | COC(=O)c1cc(C(O)CNC(C)(C)CCn2cncn2)ccc1OCc1ccccc1 | CC(C)(CCn1cncn1)NCC(O)c1ccc(OCc2ccccc2)c(CO)c1 | null | null | null | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(COc2ccc(CCNCCCn3cncn3)cc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 7.6 g of methyl 2-benzyloxy-5-[2-[1,1-dimethyl-3-[1,2,4]triazol-1-yl-propylamino]-1-hydroxy-ethyl]-benzoate are reduced in an ethanolic calcium chloride solution with sodium borohydride as described for Example 1c. The product is obtained as a colourless oil after purification by column chromatography (CHCl3/MeOH/NH3=9... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1nc[nH]n1.c1ccccc1.c1ccccc1 | Other | null | null | null | COC(=O)c1cc(C(O)CNC(C)(C)CCn2cncn2)ccc1OCc1ccccc1>>CC(C)(CCn1cncn1)NCC(O)c1ccc(OCc2ccccc2)c(CO)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f373ea10a6a84604b61c0f16d566114d | CC(C)(CCn1cncn1)NCC(O)c1ccc(OCc2ccccc2)c(CO)c1>>CC(C)(CCn1cncn1)NCC(O)c1ccc(O)c(CO)c1 | C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C(CNC(CCN1N=CN=C1)(C)C)O)CO>>CC(CCN1N=CN=C1)(C)NCC(O)C1=CC(=C(C=C1)O)CO | c1ccc(C[O:19][c:18]2[cH:17][cH:16][c:15]([CH:13]([CH2:12][NH:11][C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][n:6]3[cH:7][n:8][cH:9][n:10]3)[OH:14])[cH:23][c:20]2[CH2:21][OH:22])cc1>>[CH3:1][C:2]([CH3:3])([CH2:4][CH2:5][n:6]1[cH:7][n:8][cH:9][n:10]1)[NH:11][CH2:12][CH:13]([OH:14])[c:15]1[cH:16][cH:17][c:18]([OH:19])[c:20]([CH2... | CC(C)(CCn1cncn1)NCC(O)c1ccc(OCc2ccccc2)c(CO)c1 | CC(C)(CCn1cncn1)NCC(O)c1ccc(O)c(CO)c1 | null | [Pd] | CO | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(CCNCCCn2cncn2)cc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | null | null | The debenzylation of 6 g of 1-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-(1,1-dimethyl-3-[1,2,4]triazol-1-yl-propylamino)-ethanol is carried out hydrogenolytically with 1 g of palladium on charcoal (5%) in 100 mL methanol. After the catalyst has been removed by suction filtering and the filtrate has been evaporated down th... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1nc[nH]n1.c1ccccc1 | Other | [Pd].CO | null | null | CC(C)(CCn1cncn1)NCC(O)c1ccc(OCc2ccccc2)c(CO)c1>[Pd].CO>CC(C)(CCn1cncn1)NCC(O)c1ccc(O)c(CO)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d01719cb473e41ad981816ef2ffe3e85 | CCOC(C)=N.Cc1ccc(C(=O)NN)cc1>>CC(=N)N(N)C(=O)c1ccc(C)cc1 | [Na].Cl.C(C)OC(C)=N.CC1=CC=C(C(=O)NN)C=C1>>N=C(C)N(N)C(C1=CC=C(C=C1)C)=O | CCO[C:2]([CH3:1])=[NH:3].[NH:4]([NH2:5])[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([CH3:12])[cH:13][cH:14]1>>[CH3:1][C:2](=[NH:3])[N:4]([NH2:5])[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([CH3:12])[cH:13][cH:14]1 | CCOC(C)=N.Cc1ccc(C(=O)NN)cc1 | CC(=N)N(N)C(=O)c1ccc(C)cc1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | fe324327bc33cfeacb108bab3ce14a06c4d02f9539f3b00ba33ac2a2ce6b4dcb | 261d643341ab1545270a23dc6e2baca2b5f0751e834201694e9fa9a615f13907 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[N;D1;H1:3].[N;D1;H2:4]-[NH;D2;+0:5]-[C:6](=[O;D1;H0:7])-[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[N;D1;H1:3])-[N;H0;D3;+0:5](-[N;D1;H2:4])-[C:6](=[O;D1;H0:7])-[c:8] | 15.7 | [{"value": 15.7, "product": "N=C(C)N(N)C(C1=CC=C(C=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | 1.65 g (72 mmol) of sodium are dissolved in 80 mL ethanol. 8.89 g (72 mmol) of ethylacetimidate hydrochloride in 160 mL ethanol are added at ambient temperature and the precipitated sodium chloride is filtered off. The filtrate is combined with 6.00 g (40 mmol) 4-methyl-benzoic acid hydrazide and stirred overnight. The... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Ether | Acylhydrazine | null | null | c1ccccc1 | HO- | C(C)O | null | 8 | CCOC(C)=N.Cc1ccc(C(=O)NN)cc1>C(C)O>CC(=N)N(N)C(=O)c1ccc(C)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a9735160f2dc458d91fffa7416777b23 | CC(C)(CCCl)NC(=O)OC(C)(C)C.Cc1ccc(-c2n[nH]c(C)n2)cc1>>Cc1ccc(-c2nc(C)n(CCC(C)(C)NC(=O)OC(C)(C)C)n2)cc1 | O.[H-].[Na+].CC1=NC(=NN1)C1=CC=C(C=C1)C.ClCCC(C)(C)NC(OC(C)(C)C)=O>>CC(CCN1N=C(N=C1C)C1=CC=C(C=C1)C)(C)NC(OC(C)(C)C)=O | Cl[CH2:11][CH2:12][C:13]([CH3:14])([CH3:15])[NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23].[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]([CH3:9])[nH:10][n:24]2)[cH:25][cH:26]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]([CH3:9])[n:10]([CH2:11][CH2:12][C:13]([CH3:14])([CH3:15])[NH:16][C:17](=[O:... | CC(C)(CCCl)NC(=O)OC(C)(C)C.Cc1ccc(-c2n[nH]c(C)n2)cc1 | Cc1ccc(-c2nc(C)n(CCC(C)(C)NC(=O)OC(C)(C)C)n2)cc1 | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | C(C)(=O)OCC.CN1CCCN(C1=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8bef00eaa42d3c717b13b9e6e5eb0aaa548aa02b0e5b8a7323f70bc5d1c7c865 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(-c2nc[nH]n2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[c:5]1:[#7;a:6]:[c:7](-[c:8]):[#7;a:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[#7;a:9]:[c:7](-[c:8]):[#7;a:6]:[c:5]:1-[C;D1;H3:4] | null | [] | null | null | 1 | HOUR | 1.35 g (34 mmol, 60%) sodium hydride are added to a solution of 4.87 g (28 mmol) of 5-methyl-3-p-tolyl-[1,2,4]triazole in 40 mL DMPU at 0° C. The reaction mixture is heated to ambient temperature and then stirred for one hour. 9.35 g (42 mmol) of tert.butyl (3-chloro-1,1-dimethyl-propyl)-carbamate and 1.87 g (5 mmol) o... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1nnc[nH]1 | c1nnc[nH]1 | c1ccccc1.c1nnc[nH]1 | HCl | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)OCC.CN1CCCN(C1=O)C | null | 1 | CC(C)(CCCl)NC(=O)OC(C)(C)C.Cc1ccc(-c2n[nH]c(C)n2)cc1>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.C(C)(=O)OCC.CN1CCCN(C1=O)C>Cc1ccc(-c2nc(C)n(CCC(C)(C)NC(=O)OC(C)(C)C)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b09313c7b74d4df39d251089e8546b43 | Cc1ccc(-c2nc(C)n(CCC(C)(C)NC(=O)OC(C)(C)C)n2)cc1>>Cc1ccc(-c2nc(C)n(CCC(C)(C)N)n2)cc1 | FC(C(=O)O)(F)F.CC(CCN1N=C(N=C1C)C1=CC=C(C=C1)C)(C)NC(OC(C)(C)C)=O>>CC(CCN1N=C(N=C1C)C1=CC=C(C=C1)C)(C)N | CC(C)(C)OC(=O)[NH:16][C:13]([CH2:12][CH2:11][n:10]1[c:8]([CH3:9])[n:7][c:6](-[c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:19][cH:18]2)[n:17]1)([CH3:14])[CH3:15]>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]([CH3:9])[n:10]([CH2:11][CH2:12][C:13]([CH3:14])([CH3:15])[NH2:16])[n:17]2)[cH:18][cH:19]1 | Cc1ccc(-c2nc(C)n(CCC(C)(C)NC(=O)OC(C)(C)C)n2)cc1 | Cc1ccc(-c2nc(C)n(CCC(C)(C)N)n2)cc1 | null | null | ClCCl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccc(-c2nc[nH]n2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[C;D1;H3:5]>>[C:3]-[C:2](-[C;D1;H3:4])(-[C;D1;H3:5])-[NH2;D1;+0:1] | null | [] | null | null | 8 | HOUR | A total of 11 mL trifluoroacetic acid are added dropwise to a solution of 2.97 g (8.3 mmol) of tert.butyl [1,1-dimethyl-3-(5-methyl-3-p-tolyl-[1,2,4]triazol-1-yl)-propyl]-carbamate in 80 mL dichloromethane and the mixture is stirred overnight at ambient temperature. The solvent is distilled off and the residue is combi... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1nnc[nH]1 | HO- | ClCCl | null | 8 | Cc1ccc(-c2nc(C)n(CCC(C)(C)NC(=O)OC(C)(C)C)n2)cc1>ClCCl>Cc1ccc(-c2nc(C)n(CCC(C)(C)N)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b2cc11185257469d8d38bfba1120cb56 | CC(C)(CCCl)NC(=O)OC(C)(C)C.Cc1nc(-c2ccc(F)cc2)n[nH]1>>Cc1nc(-c2ccc(F)cc2)nn1CCC(C)(C)NC(=O)OC(C)(C)C | ClCCC(C)(C)NC(OC(C)(C)C)=O.[H-].[Na+].FC1=CC=C(C=C1)C1=NNC(=N1)C>>FC1=CC=C(C=C1)C1=NN(C(=N1)C)CCC(C)(C)NC(OC(C)(C)C)=O | Cl[CH2:14][CH2:15][C:16]([CH3:17])([CH3:18])[NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26].[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]2)[n:12][nH:13]1>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]2)[n:12][n:13]1[CH2:14][CH2:15][C:16]([CH3:17])([CH3:18])... | CC(C)(CCCl)NC(=O)OC(C)(C)C.Cc1nc(-c2ccc(F)cc2)n[nH]1 | Cc1nc(-c2ccc(F)cc2)nn1CCC(C)(C)NC(=O)OC(C)(C)C | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | CN1CCCN(C1=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8bef00eaa42d3c717b13b9e6e5eb0aaa548aa02b0e5b8a7323f70bc5d1c7c865 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(-c2nc[nH]n2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[c:5]1:[#7;a:6]:[c:7](-[c:8]):[#7;a:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[#7;a:9]:[c:7](-[c:8]):[#7;a:6]:[c:5]:1-[C;D1;H3:4] | null | [] | null | null | null | null | 5.88 g (33 mmol) of 3-(4-fluoro-phenyl)-5-methyl-[1,2,4]triazole are dissolved in 40 mL DMPU and reacted with 11.04 g (50 mmol) of tert.butyl (3-chloro-1,1-dimethyl-propyl)-carbamate, 1.59 g (40 mmol, 60%) of sodium hydride and 2.21 g (6 mmol) of tetrabutylammonium iodide in the manner described in P-1-c).
Conditions: ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1nnc[nH]1 | c1nnc[nH]1 | c1nnc[nH]1.c1ccccc1 | HCl | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN1CCCN(C1=O)C | null | null | CC(C)(CCCl)NC(=O)OC(C)(C)C.Cc1nc(-c2ccc(F)cc2)n[nH]1>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN1CCCN(C1=O)C>Cc1nc(-c2ccc(F)cc2)nn1CCC(C)(C)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-be8785509a74442a8b9d8d877d506d40 | CC(C)(CCCl)NC(=O)OC(C)(C)C.Cc1nc(-c2cc(F)cc(F)c2)n[nH]1>>Cc1nc(-c2cc(F)cc(F)c2)nn1CCC(C)(C)NC(=O)OC(C)(C)C | FC=1C=C(C=C(C1)F)C1=NNC(=N1)C.[H-].[Na+].ClCCC(C)(C)NC(OC(C)(C)C)=O>>FC=1C=C(C=C(C1)F)C1=NN(C(=N1)C)CCC(C)(C)NC(OC(C)(C)C)=O | Cl[CH2:15][CH2:16][C:17]([CH3:18])([CH3:19])[NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27].[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][c:7]([F:8])[cH:9][c:10]([F:11])[cH:12]2)[n:13][nH:14]1>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][c:7]([F:8])[cH:9][c:10]([F:11])[cH:12]2)[n:13][n:14]1[CH2:15][CH2:16][C:17]([CH3:... | CC(C)(CCCl)NC(=O)OC(C)(C)C.Cc1nc(-c2cc(F)cc(F)c2)n[nH]1 | Cc1nc(-c2cc(F)cc(F)c2)nn1CCC(C)(C)NC(=O)OC(C)(C)C | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | CN1CCCN(C1=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8bef00eaa42d3c717b13b9e6e5eb0aaa548aa02b0e5b8a7323f70bc5d1c7c865 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1ccc(-c2nc[nH]n2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[C:3].[C;D1;H3:4]-[c:5]1:[#7;a:6]:[c:7](-[c:8]):[#7;a:9]:[nH;D2;+0:10]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:10]1:[#7;a:9]:[c:7](-[c:8]):[#7;a:6]:[c:5]:1-[C;D1;H3:4] | null | [] | null | null | null | null | 3.74 g (19 mmol) of 3-(3,5-difluoro-phenyl)-5-methyl-[1,2,4]triazole in 25 mL DMPU are reacted with 0.92 g (23 mmol, 60%) of sodium hydride, 6.37 g (29 mmol) of tert.butyl (3-chloro-1,1-dimethyl-propyl)-carbamate and 1.27 g (3.5 mmol) of tetrabutylammonium iodide analogously to P-1-c). Oil.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1nnc[nH]1 | c1nnc[nH]1 | c1nnc[nH]1.c1ccccc1 | HCl | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN1CCCN(C1=O)C | null | null | CC(C)(CCCl)NC(=O)OC(C)(C)C.Cc1nc(-c2cc(F)cc(F)c2)n[nH]1>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN1CCCN(C1=O)C>Cc1nc(-c2cc(F)cc(F)c2)nn1CCC(C)(C)NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-00c1178714e54103bd2c468d0d4bb1bd | CCC(=N)N.COc1ccc(C(=O)NN)cc1>>CCC(=N)N(N)C(=O)c1ccc(OC)cc1 | Cl.C(CC)(=N)N.COC1=CC=C(C(=O)NN)C=C1>>N=C(CC)N(N)C(C1=CC=C(C=C1)OC)=O | N[C:3]([CH2:2][CH3:1])=[NH:4].[NH:5]([NH2:6])[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]1>>[CH3:1][CH2:2][C:3](=[NH:4])[N:5]([NH2:6])[C:7](=[O:8])[c:9]1[cH:10][cH:11][c:12]([O:13][CH3:14])[cH:15][cH:16]1 | CCC(=N)N.COc1ccc(C(=O)NN)cc1 | CCC(=N)N(N)C(=O)c1ccc(OC)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 881186226d68555da074f393b7f41ec9b9a8312187844874bad4ad0ff35d9a64 | 29975e1d65e16090ba2ff7b9d7c27d2b9cd4263bd4cf95c313c0d29e9a47bc8f | c1ccccc1 | N-[C;H0;D3;+0:1](=[N;D1;H1:2])-[C:3]-[C;D1;H3:4].[N;D1;H2:5]-[NH;D2;+0:6]-[C:7](=[O;D1;H0:8])-[c:9]>>[C;D1;H3:4]-[C:3]-[C;H0;D3;+0:1](=[N;D1;H1:2])-[N;H0;D3;+0:6](-[N;D1;H2:5])-[C:7](=[O;D1;H0:8])-[c:9] | null | [] | null | null | null | null | Prepared from 4.90 g (45 mmol) of propioamidine hydrochloride and 5.00 g (30 mmol) of 4-methoxy-benzoic acid hydrazide analogously to the method described in P-1-a). After the ethanol has been distilled off 10.0 g of crude product are obtained which are reacted without any further purification.
Conditions: See reaction... | 10.6084/m9.figshare.5104873.v1 | null | Acylhydrazine.Primary amine | Acylhydrazine | null | null | c1ccccc1 | Other | null | null | null | CCC(=N)N.COc1ccc(C(=O)NN)cc1>>CCC(=N)N(N)C(=O)c1ccc(OC)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5e6f2fd3a3bf42e88505fcf3d36a1220 | CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1.Cc1ccc(-c2nc(C)n(CCC(C)(C)N)n2)cc1>>Cc1ccc(-c2nc(C)n(CCC(C)(C)NCC(O)c3ccc(O)c(CO)c3)n2)cc1 | C(C1=CC=CC=C1)OC1=C(C(=O)OC)C=C(C=C1)C(C(O)OCC)=O.CC(CCN1N=C(N=C1C)C1=CC=C(C=C1)C)(C)N>>CC(CCN1N=C(N=C1C)C1=CC=C(C=C1)C)(C)NCC(O)C1=CC(=C(C=C1)O)CO | CCO[CH:17](O)[C:18](=[O:19])[c:20]1[cH:21][cH:22][c:23]([O:24]Cc2ccccc2)[c:25]([C:26](OC)=[O:27])[cH:28]1.[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]([CH3:9])[n:10]([CH2:11][CH2:12][C:13]([CH3:14])([CH3:15])[NH2:16])[n:29]2)[cH:30][cH:31]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][c:8]([CH3:9])[n:10]([CH2:11][C... | CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1.Cc1ccc(-c2nc(C)n(CCC(C)(C)N)n2)cc1 | Cc1ccc(-c2nc(C)n(CCC(C)(C)NCC(O)c3ccc(O)c(CO)c3)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 34f8f4a6788d6c681d3e1d1d0ca8cdb0b22b34660b85a60626fbfbee66b0a978 | 4448e1ae18d5453e19796a86532c96366da07d8e645a2eff499c2e2676c0517a | c1ccc(CCNCCCn2cnc(-c3ccccc3)n2)cc1 | C-C-O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]1:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-C-c2:c:c:c:c:c:2):[c:9](-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-O-C):[c:12]:1.[C:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[NH2;D1;+0:17]>>[C:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[NH;D2;+0:17]-[CH2;D2;+0:1]-[CH;D3;+0:2](-[OH;D... | null | [] | null | null | null | null | The compound is prepared analogously to the general working method A from 241 mg (0.7 mmol) of methyl 2-benzyloxy-5-(2-ethoxy-2-hydroxy-acetyl)-benzoate and 181 mg (0.7 mmol) of 1,1-dimethyl-3-(5-methyl-3-p-tolyl-[1,2,4]triazol-1-yl)-propylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ether.Ether.Secondary alcohol.Primary amine | Primary alcohol.Secondary alcohol.Aromatic alcohol.Secondary amine | c1ccccc1 | null | c1ccccc1.c1nnc[nH]1.c1ccccc1 | HO- | null | null | null | CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1.Cc1ccc(-c2nc(C)n(CCC(C)(C)N)n2)cc1>>Cc1ccc(-c2nc(C)n(CCC(C)(C)NCC(O)c3ccc(O)c(CO)c3)n2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-06dc23e17530430893a7bcabb9eda233 | CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1.Cc1nc(-c2cc(F)cc(F)c2)nn1CCC(C)(C)N>>Cc1nc(-c2cc(F)cc(F)c2)nn1CCC(C)(C)NCC(O)c1ccc(O)c(CO)c1 | C(C1=CC=CC=C1)OC1=C(C(=O)OC)C=C(C=C1)C(C(O)OCC)=O.FC=1C=C(C=C(C1)F)C1=NN(C(=N1)C)CCC(C)(C)N>>FC=1C=C(C=C(C1)F)C1=NN(C(=N1)C)CCC(C)(C)NCC(O)C1=CC(=C(C=C1)O)CO | CCO[CH:21](O)[C:22](=[O:23])[c:24]1[cH:25][cH:26][c:27]([O:28]Cc2ccccc2)[c:29]([C:30](OC)=[O:31])[cH:32]1.[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][c:7]([F:8])[cH:9][c:10]([F:11])[cH:12]2)[n:13][n:14]1[CH2:15][CH2:16][C:17]([CH3:18])([CH3:19])[NH2:20]>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][c:7]([F:8])[cH:9][c:10]([F:11])[c... | CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1.Cc1nc(-c2cc(F)cc(F)c2)nn1CCC(C)(C)N | Cc1nc(-c2cc(F)cc(F)c2)nn1CCC(C)(C)NCC(O)c1ccc(O)c(CO)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 34f8f4a6788d6c681d3e1d1d0ca8cdb0b22b34660b85a60626fbfbee66b0a978 | 4448e1ae18d5453e19796a86532c96366da07d8e645a2eff499c2e2676c0517a | c1ccc(CCNCCCn2cnc(-c3ccccc3)n2)cc1 | C-C-O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]1:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-C-c2:c:c:c:c:c:2):[c:9](-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-O-C):[c:12]:1.[C:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[NH2;D1;+0:17]>>[C:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[NH;D2;+0:17]-[CH2;D2;+0:1]-[CH;D3;+0:2](-[OH;D... | null | [] | null | null | null | null | The compound is obtained according to general working method A from 121 mg (0.35 mmol) of methyl 2-benzyloxy-5-(2-ethoxy-2-hydroxy-acetyl)-benzoate and 98 mg (0.35 mmol) of 3-[3-(3,5-difluoro-phenyl)-5-methyl-[1,2,4]triazol-1-yl]-1,1-dimethyl-propylamine. Yield: 9 mg (6%); mass spectroscopy [M+H]+=447.
Conditions: See ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ether.Ether.Secondary alcohol.Primary amine | Primary alcohol.Secondary alcohol.Aromatic alcohol.Secondary amine | c1ccccc1 | null | c1nnc[nH]1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1.Cc1nc(-c2cc(F)cc(F)c2)nn1CCC(C)(C)N>>Cc1nc(-c2cc(F)cc(F)c2)nn1CCC(C)(C)NCC(O)c1ccc(O)c(CO)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e5d952dab2484b08a7aa51cb7c6ebfd4 | CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1.Cc1nc(-c2ccc(F)cc2)nn1CCC(C)(C)N>>Cc1nc(-c2ccc(F)cc2)nn1CCC(C)(C)NCC(O)c1ccc(O)c(CO)c1 | C(C1=CC=CC=C1)OC1=C(C(=O)OC)C=C(C=C1)C(C(O)OCC)=O.FC1=CC=C(C=C1)C1=NN(C(=N1)C)CCC(C)(C)N>>FC1=CC=C(C=C1)C1=NN(C(=N1)C)CCC(C)(C)NCC(O)C1=CC(=C(C=C1)O)CO | CCO[CH:20](O)[C:21](=[O:22])[c:23]1[cH:24][cH:25][c:26]([O:27]Cc2ccccc2)[c:28]([C:29](OC)=[O:30])[cH:31]1.[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]2)[n:12][n:13]1[CH2:14][CH2:15][C:16]([CH3:17])([CH3:18])[NH2:19]>>[CH3:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]2)[n:12][... | CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1.Cc1nc(-c2ccc(F)cc2)nn1CCC(C)(C)N | Cc1nc(-c2ccc(F)cc2)nn1CCC(C)(C)NCC(O)c1ccc(O)c(CO)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 34f8f4a6788d6c681d3e1d1d0ca8cdb0b22b34660b85a60626fbfbee66b0a978 | 4448e1ae18d5453e19796a86532c96366da07d8e645a2eff499c2e2676c0517a | c1ccc(CCNCCCn2cnc(-c3ccccc3)n2)cc1 | C-C-O-[CH;D3;+0:1](-O)-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4]1:[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-C-c2:c:c:c:c:c:2):[c:9](-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-O-C):[c:12]:1.[C:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[NH2;D1;+0:17]>>[C:13]-[C:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[NH;D2;+0:17]-[CH2;D2;+0:1]-[CH;D3;+0:2](-[OH;D... | null | [] | null | null | null | null | Prepared according to general working method A from 344 mg (1 mmol) of methyl 2-benzyloxy-5-(2-ethoxy-2-hydroxy-acetyl)-benzoate and 262 mg (1 mmol) of 3-[3-(4-fluoro-phenyl)-5-methyl-[1,2,4]triazol-1-yl]-1,1-dimethyl-propylamine.
Conditions: See reaction.notes.procedure_details.
Workup: Prepared | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ether.Ether.Secondary alcohol.Primary amine | Primary alcohol.Secondary alcohol.Aromatic alcohol.Secondary amine | c1ccccc1 | null | c1nnc[nH]1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CCOC(O)C(=O)c1ccc(OCc2ccccc2)c(C(=O)OC)c1.Cc1nc(-c2ccc(F)cc2)nn1CCC(C)(C)N>>Cc1nc(-c2ccc(F)cc2)nn1CCC(C)(C)NCC(O)c1ccc(O)c(CO)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0846c3af3db74fb580a9cab8a8c1a031 | CC(O)CN.O=C(Cl)OCc1ccccc1>>CC(O)CNC(=O)OCc1ccccc1 | NCC(C)O.ClC(=O)OCC1=CC=CC=C1.C([O-])([O-])=O.[Na+].[Na+]>>C(C1=CC=CC=C1)OC(=O)NCC(C)O | [CH3:1][CH:2]([OH:3])[CH2:4][NH2:5].Cl[C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][CH:2]([OH:3])[CH2:4][NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | CC(O)CN.O=C(Cl)OCc1ccccc1 | CC(O)CNC(=O)OCc1ccccc1 | null | null | O | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[C:5]-[C:6]-[NH2;D1;+0:7]>>[C:5]-[C:6]-[NH;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4] | 100 | [{"value": 100.0, "product": "C(C1=CC=CC=C1)OC(=O)NCC(C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.8, "product": "C(C1=CC=CC=C1)OC(=O)NCC(C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 3 | HOUR | A mixture of 1-amino-2-propanol (1) (4.6 g, 61.8 mmol), benzyl chloroformate (11.5 g, 67.6 mmol), and sodium carbonate (7.16 g, 67.7 mmol) in water (50 mL) was stirred at 0° C. for 3 h. Water (50 mL) was added to the reaction mixture, the product was extracted with CH2Cl2 (3×20 mL), dried over Na2SO4 and concentrated. ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1ccccc1 | HCl | O | 0 | 3 | CC(O)CN.O=C(Cl)OCc1ccccc1>O>CC(O)CNC(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-94190286fc6e4421925b30e93ae48177 | CC(O)CNC(=O)OCc1ccccc1>>CC(=O)CNC(=O)OCc1ccccc1 | CCN(CC)CC.C(C1=CC=CC=C1)OC(=O)NCC(C)O.C(C(=O)Cl)(=O)Cl.CS(=O)C>>C(C1=CC=CC=C1)OC(=O)NCC(C)=O | [CH3:1][CH:2]([OH:3])[CH2:4][NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][C:2](=[O:3])[CH2:4][NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | CC(O)CNC(=O)OCc1ccccc1 | CC(=O)CNC(=O)OCc1ccccc1 | null | null | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | c1ccccc1 | [C;D1;H3:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[C:4]-[#7:5]-[C:6]=[O;D1;H0:7]>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[C:4]-[#7:5]-[C:6]=[O;D1;H0:7] | 81 | [{"value": 81.0, "product": "C(C1=CC=CC=C1)OC(=O)NCC(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.6, "product": "C(C1=CC=CC=C1)OC(=O)NCC(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 20 | MINUTE | To a solution of oxalyl chloride (37 mL, 2 M solution in CH2Cl2, 74 mmol) in CH2Cl2 (60 mL) at −78° C. under argon was added DMSO (7.8 g, 100 mmol). The mixture was stirred at −78° C. for 20 min, and to this mixture was added a solution of 1-benzyloxycarbonylamino-2-propanol (2) (12.9 g, 61.8 mmol) in CH2Cl2 (40 mL). T... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1 | null | C(Cl)Cl | -78 | 0.333333 | CC(O)CNC(=O)OCc1ccccc1>C(Cl)Cl>CC(=O)CNC(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-67649b5714094ab7943abcf6ed07b1b7 | CC(=O)CN.O=C(O)C(Cc1ccc(OCc2ccccc2)cc1)N1C(=O)c2ccccc2C1=O>>CC(=O)CNC(=O)C(Cc1ccc(OCc2ccccc2)cc1)N1C(=O)c2ccccc2C1=O | Cl.NCC(C)=O.C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(C(=O)O)N1C(C2=CC=CC=C2C1=O)=O.C=1C=CC2=C(C1)N=NN2O.CCN=C=NCCCN(C)C.CCN(CC)CC>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(C(=O)NCC(C)=O)N1C(C2=CC=CC=C2C1=O)=O | [CH3:1][C:2](=[O:3])[CH2:4][NH2:5].O[C:6](=[O:7])[CH:8]([CH2:9][c:10]1[cH:11][cH:12][c:13]([O:14][CH2:15][c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)[cH:22][cH:23]1)[N:24]1[C:25](=[O:26])[c:27]2[cH:28][cH:29][cH:30][cH:31][c:32]2[C:33]1=[O:34]>>[CH3:1][C:2](=[O:3])[CH2:4][NH:5][C:6](=[O:7])[CH:8]([CH2:9][c:10]1[cH:11][... | CC(=O)CN.O=C(O)C(Cc1ccc(OCc2ccccc2)cc1)N1C(=O)c2ccccc2C1=O | CC(=O)CNC(=O)C(Cc1ccc(OCc2ccccc2)cc1)N1C(=O)c2ccccc2C1=O | null | null | O.CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C1c2ccccc2C(=O)N1CCc1ccc(OCc2ccccc2)cc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[#7:5](-[C:6]=[O;D1;H0:7])-[C:8]=[O;D1;H0:9].[C;D1;H3:10]-[C:11](=[O;D1;H0:12])-[C:13]-[NH2;D1;+0:14]>>[C:4]-[C:3](-[#7:5](-[C:6]=[O;D1;H0:7])-[C:8]=[O;D1;H0:9])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:14]-[C:13]-[C:11](-[C;D1;H3:10])=[O;D1;H0:12] | 88 | [{"value": 88.0, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(C(=O)NCC(C)=O)N1C(C2=CC=CC=C2C1=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.6, "product": "C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(C(=O)NCC(C)=O)N1C(C2=CC=CC=C2C1=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 0.5 | HOUR | A mixture of 3-(4-benzyloxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid (500 mg, 1.25 mmol), HOBt (180 mg, 2.5 mmol), and EDCI (480 mg, 2.5 mmol) in DMF (3 mL) was stirred at 0° C. for 0.5 h. To this mixture was added 1-amino-2-propanone hydrochloride (4) (272 mg, 2.5 mmol) followed by Et3N (550 □L, ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccc2c(c1)C[NH]C2 | HO- | O.CN(C)C=O | 0 | 0.5 | CC(=O)CN.O=C(O)C(Cc1ccc(OCc2ccccc2)cc1)N1C(=O)c2ccccc2C1=O>O.CN(C)C=O>CC(=O)CNC(=O)C(Cc1ccc(OCc2ccccc2)cc1)N1C(=O)c2ccccc2C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d2f816afef8946e591b0b16b2214f1a5 | CC(=O)CNC(=O)C(Cc1ccc(OCc2ccccc2)cc1)N1C(=O)c2ccccc2C1=O>>CC(=O)Oc1ccc(CC(c2ncc(C)o2)N2C(=O)c3ccccc3C2=O)cc1 | C(C)(=O)[O-].[Na+].C(C1=CC=CC=C1)OC1=CC=C(C=C1)CC(C(=O)NCC(C)=O)N1C(C2=CC=CC=C2C1=O)=O.S(O)(O)(=O)=O>>O=C1N(C(C2=CC=CC=C12)=O)C(CC1=CC=C(C=C1)OC(C)=O)C=1OC(=CN1)C | O=[C:14]([CH2:13][NH:12][C:11]([CH:10]([CH2:9][c:8]1[cH:7][cH:6][c:5]([O:4]Cc2ccccc2)[cH:29][cH:28]1)[N:17]1[C:18](=[O:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26]1=[O:27])=[O:16])[CH3:15]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([CH2:9][CH:10]([c:11]2[n:12][cH:13][c:14]([CH3:15])[o:16]2)[N:17]2[C:18](... | CC(=O)CNC(=O)C(Cc1ccc(OCc2ccccc2)cc1)N1C(=O)c2ccccc2C1=O | CC(=O)Oc1ccc(CC(c2ncc(C)o2)N2C(=O)c3ccccc3C2=O)cc1 | null | null | C(C)(=O)OC(C)=O | Reduction | OtherReaction | c7bc602c79cc0d343fab98c3a176bdd6786ca2e12fbca669ada54bed1717a521 | 97e2ecf86f40b2e93e098f38aa85ca1db95baab3228abb0fdcc72152492d8f10 | O=C1c2ccccc2C(=O)N1C(Cc1ccccc1)c1ncco1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[CH2;D2;+0:3]-[NH;D2;+0:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[C:7](-[C:8])-[#7:9](-[C:10]=[O;D1;H0:11])-[C:12]=[O;D1;H0:13].[c:14]:[c:15](-[O;H0;D2;+0:16]-C-c1:c:c:c:c:c:1):[c:17]>>[C;D1;H3:18]-[C:19](=[O;D1;H0:20])-[O;H0;D2;+0:16]-[c:15](:[c:14]):[c:17].[C:8]-[C:7](-[#7:9](-[C:10]=[O;D1;H0... | 56 | [{"value": 56.0, "product": "O=C1N(C(C2=CC=CC=C12)=O)C(CC1=CC=C(C=C1)OC(C)=O)C=1OC(=CN1)C", "details": "PERCENTYIELD", "is_desired": false}] | 57.5 | CELSIUS | 2 | HOUR | To a solution of 3-(4-Benzyloxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-N-(2-oxo-propyl)-propionamide (5) (220 mg, 0.5 mmol) in acetic anhydride (2 mL) at room temperature was added concentrated sulfuric acid (0.2 mL). The mixture was stirred at 55-60° C. for 2 h, then sodium acetate (200 mg) was added, and the... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Secondary amide | Ester | c1ccccc1 | c1cocn1 | c1ccccc1.c1cocn1.c1ccc2c(c1)C[NH]C2 | HO- | C(C)(=O)OC(C)=O | 57.5 | 2 | CC(=O)CNC(=O)C(Cc1ccc(OCc2ccccc2)cc1)N1C(=O)c2ccccc2C1=O>C(C)(=O)OC(C)=O>CC(=O)Oc1ccc(CC(c2ncc(C)o2)N2C(=O)c3ccccc3C2=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2b99da6e97b8436a8959456d82cfddc4 | CC(O)CN.Cc1ccccc1.O=C1OC(=O)c2ccccc21>>CC(O)CNC(=O)OCc1ccccc1 | NCC(C)O.C1(C=2C(C(=O)O1)=CC=CC2)=O.C(C)N(CC)CC.C1(=CC=CC=C1)C>>C(C1=CC=CC=C1)OC(=O)NCC(C)O | [CH3:1][CH:2]([OH:3])[CH2:4][NH2:5].[CH3:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1.O=C1c2ccccc2[C:6](=[O:7])[O:8]1>>[CH3:1][CH:2]([OH:3])[CH2:4][NH:5][C:6](=[O:7])[O:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1 | CC(O)CN.Cc1ccccc1.O=C1OC(=O)c2ccccc21 | CC(O)CNC(=O)OCc1ccccc1 | null | null | O | Protection | OtherReaction | f7c969f78f0ccd827c55ebd06a1de19d35b3212f4ea0cbd9b6f08cc094d1e863 | d9c1951fa6bdd53d2581c243a75e964e0e16f6982143c2014721802f893c561b | c1ccccc1 | O=C1-[O;H0;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-c2:c:c:c:c:c:2-1.[CH3;D1;+0:4]-[c:5](:[c:6]):[c:7].[C:8]-[C:9]-[NH2;D1;+0:10]>>[C:8]-[C:9]-[NH;D2;+0:10]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[O;H0;D2;+0:1]-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7] | 142.1 | [{"value": 142.1, "product": "C(C1=CC=CC=C1)OC(=O)NCC(C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a round bottom flask equipped with Dean-Stark trap was added (1) (2 g, 7.4 mmol), phthalic anhydride (1.1 g, 7.4 mmol), triethylamine (0.1 mL) and toluene (50 mL). The reaction mixture was heated to reflux and water produced was collected. After refluxing for 2 hours, the solvent was removed. The residue was acidifi... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Ester.Ester.Primary amine | Carbamic ester.Ether | c1ccc2c(c1)COC2 | null | c1ccccc1 | HO- | O | null | null | CC(O)CN.Cc1ccccc1.O=C1OC(=O)c2ccccc21>O>CC(O)CNC(=O)OCc1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9224b47530c142a5b1621a88637ebdc4 | CC(=O)c1cc(N)ccc1Cl.CS(=O)(=O)Cl>>CC(=O)c1cc(NS(C)(=O)=O)ccc1Cl | NC=1C=CC(=C(C1)C(C)=O)Cl.CS(=O)(=O)Cl.O>>C(C)(=O)C=1C=C(C=CC1Cl)NS(=O)(=O)C | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([NH2:7])[cH:12][cH:13][c:14]1[Cl:15].Cl[S:8]([CH3:9])(=[O:10])=[O:11]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([NH:7][S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][cH:13][c:14]1[Cl:15] | CC(=O)c1cc(N)ccc1Cl.CS(=O)(=O)Cl | CC(=O)c1cc(NS(C)(=O)=O)ccc1Cl | null | null | C1(=CC=CC=C1)C | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | c1ccccc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 50 | MINUTE | 1-(5-Amino-2-chlorophenyl)ethanone (411 mg; synthesized by the process reported by Radziejewski et al., Heterocycles, vol. 26, pp. 1227-1238, 1987) was dissolved in toluene (5 mL), and pyridine(235 μL) and methanesulfonyl chloride (225 μL) were added. The resulting mixture was stirred at room temperature for 50 minutes... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | 0.833333 | CC(=O)c1cc(N)ccc1Cl.CS(=O)(=O)Cl>C1(=CC=CC=C1)C>CC(=O)c1cc(NS(C)(=O)=O)ccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-88f3058c955b41cdbf67bba058084b87 | BrBr.CC(=O)c1cc(NS(C)(=O)=O)ccc1Cl>>CS(=O)(=O)Nc1ccc(Cl)c(C(=O)CBr)c1 | C(C)(=O)C=1C=C(C=CC1Cl)NS(=O)(=O)C.BrBr>>BrCC(=O)C=1C=C(C=CC1Cl)NS(=O)(=O)C | Br[Br:15].[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]([C:12](=[O:13])[CH3:14])[cH:16]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([Cl:10])[c:11]([C:12](=[O:13])[CH2:14][Br:15])[cH:16]1 | BrBr.CC(=O)c1cc(NS(C)(=O)=O)ccc1Cl | CS(=O)(=O)Nc1ccc(Cl)c(C(=O)CBr)c1 | null | null | O1CCOCC1 | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | 1 | HOUR | N-(3-acetyl-4-chlorophenyl)methanesulfonamide (300 mg) was dissolved in dioxane (5 mL), and bromine (77 μL) was added dropwise with ice-cooling. After stirring at room temperature for 1 hour, the solvent was distilled off under reduced pressure. The residue was washed with a water/ethanol mixture (1:1) and then dried u... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | O1CCOCC1 | null | 1 | BrBr.CC(=O)c1cc(NS(C)(=O)=O)ccc1Cl>O1CCOCC1>CS(=O)(=O)Nc1ccc(Cl)c(C(=O)CBr)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d8616594c0d04ca5a9f372657f02e4e1 | CS(=O)(=O)Cl.Nc1cc(C(=O)c2ccccc2)cc([N+](=O)[O-])c1>>CC(=O)c1cc(NS(C)(=O)=O)cc([N+](=O)[O-])c1 | O.NC=1C=C(C(=O)C2=CC=CC=C2)C=C(C1)[N+](=O)[O-].CS(=O)(=O)Cl.CS(=O)(=O)Cl>>C(C)(=O)C=1C=C(C=C(C1)[N+](=O)[O-])NS(=O)(=O)C | Cl[S:8]([CH3:9])(=[O:10])=[O:11].c1cc[c:1]([C:2](=[O:3])[c:4]2[cH:5][c:6]([NH2:7])[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]2)cc1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([NH:7][S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17]1 | CS(=O)(=O)Cl.Nc1cc(C(=O)c2ccccc2)cc([N+](=O)[O-])c1 | CC(=O)c1cc(NS(C)(=O)=O)cc([N+](=O)[O-])c1 | null | null | N1=CC=CC=C1 | Acylation | OtherReaction | 86cfa56c5c936672a8e8d7b1baae400b2d2392c6c11f99c71b83851b67486cc6 | f84ee06fcaf2219fbd11c25e4c02a711528f4b8b23209196daa28d2a0a918e34 | c1ccccc1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]:[c:9]-[C:10](=[O;D1;H0:11])-[c;H0;D3;+0:12]1:c:c:c:c:c:1>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]:[c:9]-[C:10](-[CH3;D1;+0:12])=[O;D1;H0:11] | null | [] | 50 | CELSIUS | 2 | HOUR | 3-Amino-5-nitrobenzophenone (4 g; synthesized by the process reported by Berend et al., J. Prakt. Chem., vol. 69, p. 471 (1904)) was dissolved in pyridine (40 mL), and the temperature was maintained at 50° C. Methanesulfonyl chloride (1.9 mL) was added, followed by stirring for 2 hours. Additional methanesulfonyl chlor... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine.Sulfonyl halide | Sulfonamide.Ketone | c1ccccc1 | null | c1ccccc1 | HCl | N1=CC=CC=C1 | 50 | 2 | CS(=O)(=O)Cl.Nc1cc(C(=O)c2ccccc2)cc([N+](=O)[O-])c1>N1=CC=CC=C1>CC(=O)c1cc(NS(C)(=O)=O)cc([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-167ee1b3ddf04ba79ea3dfdb6e0c7ce9 | BrBr.CC(=O)c1cc(Cl)cc(NS(C)(=O)=O)c1>>CS(=O)(=O)Nc1cc(Cl)cc(C(=O)CBr)c1 | C(C)(=O)C=1C=C(C=C(C1)Cl)NS(=O)(=O)C.BrBr.O>>BrCC(=O)C=1C=C(C=C(C1)Cl)NS(=O)(=O)C | Br[Br:15].[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][c:8]([Cl:9])[cH:10][c:11]([C:12](=[O:13])[CH3:14])[cH:16]1>>[CH3:1][S:2](=[O:3])(=[O:4])[NH:5][c:6]1[cH:7][c:8]([Cl:9])[cH:10][c:11]([C:12](=[O:13])[CH2:14][Br:15])[cH:16]1 | BrBr.CC(=O)c1cc(Cl)cc(NS(C)(=O)=O)c1 | CS(=O)(=O)Nc1cc(Cl)cc(C(=O)CBr)c1 | null | null | O1CCOCC1 | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | Br-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | 50 | CELSIUS | 30 | MINUTE | N-(3-acetyl-5-chlorophenyl)methanesulfonamide (500 mg) was dissolved in dioxane (10 mL). The temperature was maintained at 50° C. and bromine (0.11 mL) was added. After stirring for 30 minutes, water (50 mL) was added to the mixture, and the mixture was extracted with ethyl acetate (50 mL). The ethyl acetate layer was ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | HBr | O1CCOCC1 | 50 | 0.5 | BrBr.CC(=O)c1cc(Cl)cc(NS(C)(=O)=O)c1>O1CCOCC1>CS(=O)(=O)Nc1cc(Cl)cc(C(=O)CBr)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1cb77ff985ea48bbb3a08fd858b47c30 | CCOC(=O)c1[nH]c2cc(OC)ccc2c1C>>CCOC(=O)c1[nH]c2cc(O)ccc2c1C | CC1=C(NC2=CC(=CC=C12)OC)C(=O)OCC.B(Br)(Br)Br.O>>CC1=C(NC2=CC(=CC=C12)O)C(=O)OCC | C[O:11][c:10]1[cH:9][c:8]2[nH:7][c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:15]([CH3:16])[c:14]2[cH:13][cH:12]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[nH:7][c:8]2[cH:9][c:10]([OH:11])[cH:12][cH:13][c:14]2[c:15]1[CH3:16] | CCOC(=O)c1[nH]c2cc(OC)ccc2c1C | CCOC(=O)c1[nH]c2cc(O)ccc2c1C | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2[nH]ccc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#7;a:6]>>[#7;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | null | [] | null | null | 40 | MINUTE | Ethyl 3-methyl-6-methoxy-1H-indole-2-carboxylate (1.00 g; synthesized according to the disclosures in the literature (Gan et al., J. Org. Chem., vol. 62, pp. 9298-9304, 1997)) was dissolved in methylene chloride (dehydrated, 13 mL), and boron tribromide (1 M/methylene chloride, 17.2 mL) was added dropwise under ice-coo... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2[nH]ccc2c1 | Other | C(Cl)Cl | null | 0.666667 | CCOC(=O)c1[nH]c2cc(OC)ccc2c1C>C(Cl)Cl>CCOC(=O)c1[nH]c2cc(O)ccc2c1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c1db8e4ae1b249e1809a6b8b9ce4932b | COCCN.O=C/C=C/c1ccccc1.O=Cc1ccc(C=CC(=O)O)cc1>>COCCN(CC=Cc1ccccc1)Cc1ccc(C=CC(=O)O)cc1 | C(=O)C1=CC=C(C=CC(=O)O)C=C1.C(\C=C\C1=CC=CC=C1)=O.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+].C(C)(C)N=C=NC(C)C.COCCN.[BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]>>COCCN(CC=CC1=CC=CC=C1)CC1=CC=C(C=C1)C=CC(=O)O | [CH3:1][O:2][CH2:3][CH2:4][NH2:5].O=[CH:6]/[CH:7]=[CH:8]/[c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1.O=[CH:15][c:16]1[cH:17][cH:18][c:19]([CH:20]=[CH:21][C:22](=[O:23])[OH:24])[cH:25][cH:26]1>>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:6][CH:7]=[CH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH2:15][c:16]1[cH:17][cH:18][c:1... | COCCN.O=C/C=C/c1ccccc1.O=Cc1ccc(C=CC(=O)O)cc1 | COCCN(CC=Cc1ccccc1)Cc1ccc(C=CC(=O)O)cc1 | null | CN(C)C=1C=CN=CC1 | C(C)(=O)O.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | caeb34b0d1f507fdfdad7625809efaadf272ca1e3abe9fad823e5db43af42099 | c96547fa32f6396bf2b14895e43dd5251c6f158a37edf6d969dcd15090496e48 | C(=Cc1ccccc1)CNCc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].O=[CH;D2;+0:5]/[C:6]=[C:7]/[c:8](:[c:9]):[c:10].[C:11]-[C:12]-[NH2;D1;+0:13]>>[C:11]-[C:12]-[N;H0;D3;+0:13](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[CH2;D2;+0:5]-[C:6]=[C:7]-[c:8](:[c:9]):[c:10] | null | [] | null | null | 24 | HOUR | Wang resin (1.1 mmol/g, 1.00 g) in a polypropylene filtration tube with a polyethylene frit was added DMF (5 mL) and CH2Cl2 (5 mL), followed by 4-formylcinnamic acid (5.5 mmol, 969 mg), DMAP (1.08 mmol, 132 mg) and diisopropylcarbodiimide (5.5 mmol, 861 μL). The mixture was shaken at room temperature for 24 hours. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Aldehyde.Primary amine | Tertiary amine | null | null | c1ccccc1.c1ccccc1 | Other | CN(C)C=1C=CN=CC1.C(C)(=O)O.CN(C)C=O | null | 24 | COCCN.O=C/C=C/c1ccccc1.O=Cc1ccc(C=CC(=O)O)cc1>CN(C)C=1C=CN=CC1.C(C)(=O)O.CN(C)C=O>COCCN(CC=Cc1ccccc1)Cc1ccc(C=CC(=O)O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-894fa63debf248a0848b52c2557f1b54 | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(O)c(C(=O)O)c1>>O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1O | NC1=CC=C(C(C(=O)O)=C1)O.C(C)N(CC)CC.FC1=C(CBr)C(=C(C(=C1F)C(F)(F)F)F)F>>OC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F | Br[CH2:8][c:9]1[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17])[F:18])[c:19]([F:20])[c:21]1[F:22].[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH2:7])[cH:23][cH:24][c:25]1[OH:26]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH:7][CH2:8][c:9]2[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17])[F:18])[c:19]([F:20])[c:2... | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(O)c(C(=O)O)c1 | O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 64 | [{"value": 64.0, "product": "OC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.7, "product": "OC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 5-aminosalicylic acid (1.02 g, 6.66 mmole, purchased from Aldrich Chemical Company, USA, A7, 980-9) and triethylamine (1 ml) in dried DMF (80 ml) was added 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (1.23 g, 7.18 mmole) (Aldrich, 40, 640-6) at room temperature under a nitrogen atmosphere. The ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | 2 | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(O)c(C(=O)O)c1>CN(C)C=O>O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a5cc683afae54cf789ffec9dbcebb847 | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc([N+](=O)[O-])c(C(=O)O)c1>>O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1[N+](=O)[O-] | NC=1C=CC(=C(C(=O)O)C1)[N+](=O)[O-].FC1=C(CBr)C(=C(C(=C1F)C(F)(F)F)F)F>>[N+](=O)([O-])C1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F | Br[CH2:8][c:9]1[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17])[F:18])[c:19]([F:20])[c:21]1[F:22].[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH2:7])[cH:23][cH:24][c:25]1[N+:26](=[O:27])[O-:28]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH:7][CH2:8][c:9]2[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17])[F:18])[c... | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc([N+](=O)[O-])c(C(=O)O)c1 | O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1[N+](=O)[O-] | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 76.3 | [{"value": 76.3, "product": "[N+](=O)([O-])C1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.4, "product": "[N+](=O)([O-])C1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the similar procedure in Synthesis Example 1, by using 5-amino-2-nitrobenzoic acid (1.03 g, 5.65 mmole) and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (1.01 g, 6.04 mmole) (ACROS, 33074-0010), 1.50 g (76.3% yield) of 2-nitro-5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)benzoic acid was obta... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HBr | null | null | null | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc([N+](=O)[O-])c(C(=O)O)c1>>O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1[N+](=O)[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c222045ee2aa408eb0a418c65a946bf8 | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(Cl)c(C(=O)O)c1>>O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1Cl | NC=1C=CC(=C(C(=O)O)C1)Cl.FC1=C(CBr)C(=C(C(=C1F)C(F)(F)F)F)F>>ClC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F | Br[CH2:8][c:9]1[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17])[F:18])[c:19]([F:20])[c:21]1[F:22].[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH2:7])[cH:23][cH:24][c:25]1[Cl:26]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH:7][CH2:8][c:9]2[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17])[F:18])[c:19]([F:20])[c:2... | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(Cl)c(C(=O)O)c1 | O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1Cl | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 85.5 | [{"value": 85.5, "product": "ClC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 85.5, "product": "ClC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the similar procedure in Synthesis Example 1, by using 5-amino-2-chlorobenzoic acid (1.02 g, 5.94 mmole) (ACROS, 32525-5000), DMF (50 ml) and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (1.16 g, 6.99 mmole), 2.04 g (85.5% yield) of 2-chloro-5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino) benzo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | null | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(Cl)c(C(=O)O)c1>CN(C)C=O>O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-390fd609b2054e69bd19397089e74dbd | O=C(O)c1cc([N+](=O)[O-])ccc1Br>>Nc1ccc(Br)c(C(=O)O)c1 | BrC1=C(C(=O)O)C=C(C=C1)[N+](=O)[O-].[H][H]>>NC=1C=CC(=C(C(=O)O)C1)Br | O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([Br:6])[c:7]([C:8](=[O:9])[OH:10])[cH:11]1>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([Br:6])[c:7]([C:8](=[O:9])[OH:10])[cH:11]1 | O=C(O)c1cc([N+](=O)[O-])ccc1Br | Nc1ccc(Br)c(C(=O)O)c1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 91.2 | [{"value": 91.2, "product": "NC=1C=CC(=C(C(=O)O)C1)Br", "details": "PERCENTYIELD", "is_desired": false}, {"value": 91.2, "product": "NC=1C=CC(=C(C(=O)O)C1)Br", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-bromo-5-nitrobenzoic acid (1.10 g, 4.06 mmol) (Aldrich, 38, 184-5), activated Pd—C (43.62 mg, 0.41 mmol) (Aldrich, 20, 569-9) in methanol (30 ml) was hydrogenated for 4 hr under 30 psi of hydrogen pressure. After the mixture was filtered, the filtrate was concentrated to give 0.80 g (91.2% yield) of 5-am... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].CO | null | null | O=C(O)c1cc([N+](=O)[O-])ccc1Br>[Pd].CO>Nc1ccc(Br)c(C(=O)O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8676b9e4f09b4e87b386240126c3f4b1 | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(Br)c(C(=O)O)c1>>O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1Br | NC=1C=CC(=C(C(=O)O)C1)Br.FC1=C(CBr)C(=C(C(=C1F)C(F)(F)F)F)F>>BrC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F | Br[CH2:8][c:9]1[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17])[F:18])[c:19]([F:20])[c:21]1[F:22].[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH2:7])[cH:23][cH:24][c:25]1[Br:26]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH:7][CH2:8][c:9]2[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17])[F:18])[c:19]([F:20])[c:2... | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(Br)c(C(=O)O)c1 | O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1Br | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 76.9 | [{"value": 76.9, "product": "BrC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.0, "product": "BrC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the similar procedure in Synthesis Example 1, by using 5-amino-2-bromobenzoic acid (1.05 g, 6.12 mmole) which was prepared from Synthesis Example (4-1), DMF (50 ml) and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (1.16 g, 6.99 mmole), 2.02 g (76.9% yield) of 2-bromo-5-(2,3,5,6-tetrafluoro-4-trifluo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | null | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(Br)c(C(=O)O)c1>CN(C)C=O>O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1Br |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-750e61fe796f4854bdffb6a3e69937e5 | Cc1ccc(N)cc1C(=O)O.Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr>>Cc1ccc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)cc1C(=O)O | NC=1C=CC(=C(C(=O)O)C1)C.FC1=C(CBr)C(=C(C(=C1F)C(F)(F)F)F)F>>CC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F | [CH3:1][c:2]1[cH:3][cH:4][c:5]([NH2:6])[cH:22][c:23]1[C:24](=[O:25])[OH:26].Br[CH2:7][c:8]1[c:9]([F:10])[c:11]([F:12])[c:13]([C:14]([F:15])([F:16])[F:17])[c:18]([F:19])[c:20]1[F:21]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([NH:6][CH2:7][c:8]2[c:9]([F:10])[c:11]([F:12])[c:13]([C:14]([F:15])([F:16])[F:17])[c:18]([F:19])[c:20]2[F:... | Cc1ccc(N)cc1C(=O)O.Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr | Cc1ccc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)cc1C(=O)O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 27 | [{"value": 27.0, "product": "CC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 26.2, "product": "CC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the similar procedure in Synthesis Example 1, by using 5-amino-2-methylbenzoic acid (2.06 g, 15.0 mmole), DMF (60 ml), TEA (4 ml), and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (5.52 ml, 17.7 mmole), 1.50 g (27.0% yield) of 2-methyl-5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)benzoic acid... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | null | Cc1ccc(N)cc1C(=O)O.Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr>CN(C)C=O>Cc1ccc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)cc1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-293ed785b3c94f7a8958f37859fb86e4 | COc1ccc(N)cc1C(=O)O.Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr>>COc1ccc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)cc1C(=O)O | NC=1C=CC(=C(C(=O)O)C1)OC.FC1=C(CBr)C(=C(C(=C1F)C(F)(F)F)F)F>>COC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH2:7])[cH:23][c:24]1[C:25](=[O:26])[OH:27].Br[CH2:8][c:9]1[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17])[F:18])[c:19]([F:20])[c:21]1[F:22]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][c:9]2[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17])[F:18])[c:19]([F:20... | COc1ccc(N)cc1C(=O)O.Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr | COc1ccc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)cc1C(=O)O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 31.5 | [{"value": 31.5, "product": "COC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 29.7, "product": "COC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the similar procedure in Synthesis Example 1, by using 5-amino-2-methoxy-benzoic acid (2.10 g, 12.7 mmole), DMF (50 ml), TEA (6 ml), and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (2.00 ml, 14.0 mmole), 1.50 g (31.5% yield) of 2-methoxy-5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)benzoic a... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | null | COc1ccc(N)cc1C(=O)O.Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr>CN(C)C=O>COc1ccc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)cc1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3c88871a490b486ba1336b695bd24fe1 | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(OC(F)(F)F)c(C(=O)O)c1>>O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1OC(F)(F)F | NC=1C=CC(=C(C(=O)O)C1)OC(F)(F)F.FC1=C(CBr)C(=C(C(=C1F)C(F)(F)F)F)F>>FC1=C(CNC=2C=CC(=C(C(=O)O)C2)OC(F)(F)F)C(=C(C(=C1F)C(F)(F)F)F)F | Br[CH2:8][c:9]1[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17])[F:18])[c:19]([F:20])[c:21]1[F:22].[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH2:7])[cH:23][cH:24][c:25]1[O:26][C:27]([F:28])([F:29])[F:30]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH:7][CH2:8][c:9]2[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17... | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(OC(F)(F)F)c(C(=O)O)c1 | O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1OC(F)(F)F | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 81 | [{"value": 81.0, "product": "FC1=C(CNC=2C=CC(=C(C(=O)O)C2)OC(F)(F)F)C(=C(C(=C1F)C(F)(F)F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.0, "product": "FC1=C(CNC=2C=CC(=C(C(=O)O)C2)OC(F)(F)F)C(=C(C(=C1F)C(F)(F)F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the similar procedure in Synthesis Example 1, by using 5-amino-2-trifluoromethoxybenzoic acid (1.35 g, 6.23 mmole), DMF (50 ml), TEA (6 ml), and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (1.10 ml, 6.73 mmole), 2.25 g (81.0% yield) of 5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)-2-trifluor... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | null | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(OC(F)(F)F)c(C(=O)O)c1>CN(C)C=O>O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1OC(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5e87e5d373204b00a309bcf30e191c85 | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(O)c([N+](=O)[O-])c1>>O=[N+]([O-])c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1O | NC1=CC(=C(C=C1)O)[N+](=O)[O-].FC1=C(CBr)C(=C(C(=C1F)C(F)(F)F)F)F>>[N+](=O)([O-])C1=C(C=CC(=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F)O | Br[CH2:8][c:9]1[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17])[F:18])[c:19]([F:20])[c:21]1[F:22].[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([NH2:7])[cH:23][cH:24][c:25]1[OH:26]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([NH:7][CH2:8][c:9]2[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17])[F:18])[c:19]([F:20])[c... | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(O)c([N+](=O)[O-])c1 | O=[N+]([O-])c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 40.1 | [{"value": 40.0, "product": "[N+](=O)([O-])C1=C(C=CC(=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 40.1, "product": "[N+](=O)([O-])C1=C(C=CC(=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the similar procedure in Synthesis Example 1, by using 4-amino-2-nitrophenol (1.00 g, 6.49 mmole), DMF (30 ml), TEA (0.5 ml), and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (1.30 g, 7.78 mmole), 1.00 g (40.0% yield) of 2-nitro-4-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)phenol was obtained... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HBr | CN(C)C=O | null | null | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(O)c([N+](=O)[O-])c1>CN(C)C=O>O=[N+]([O-])c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d5107375989e46bfbb8c0e6718b327ab | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(O)c(Cl)c1>>Cc1c(F)c(F)c(CNc2ccc(Cl)c(O)c2)c(F)c1F | CN(C)C=O.NC1=CC(=C(C=C1)O)Cl.FC1=C(CBr)C(=C(C(=C1F)C(F)(F)F)F)F>>ClC1=C(C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C)F)F)O | F[C:1](F)(F)[c:2]1[c:3]([F:4])[c:5]([F:6])[c:7]([CH2:8]Br)[c:18]([F:19])[c:20]1[F:21].[NH2:9][c:10]1[cH:11][cH:12][c:13]([OH:16])[c:15]([Cl:14])[cH:17]1>>[CH3:1][c:2]1[c:3]([F:4])[c:5]([F:6])[c:7]([CH2:8][NH:9][c:10]2[cH:11][cH:12][c:13]([Cl:14])[c:15]([OH:16])[cH:17]2)[c:18]([F:19])[c:20]1[F:21] | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(O)c(Cl)c1 | Cc1c(F)c(F)c(CNc2ccc(Cl)c(O)c2)c(F)c1F | null | null | null | Functional Group Interconversion | OtherReaction | 2f5fbc13bfdd659219d4acdbee0ba26495de3c7de2f9d8b612cbb13c8b331405 | 3c5408e040084c21855dd371e440694eff7bc6aaa42a994d1e1f5aa792221f78 | c1ccc(CNc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[C;H0;D4;+0:6](-F)(-F)-F):[c:7]:[c:8]:1.[Cl;H0;D1;+0:9]-[c;H0;D3;+0:10]1:[c:11]:[c:12](-[NH2;D1;+0:13]):[c:14]:[c:15]:[c;H0;D3;+0:16]:1-[OH;D1;+0:17]>>[CH3;D1;+0:6]-[c:5]1:[c:4]:[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:13]-[c:12]2:[c:14]:[c:15]:[c;H0;D3;+0:16](-[Cl;H0;D1;+0:9]):[c... | 76 | [{"value": 76.0, "product": "ClC1=C(C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C)F)F)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the similar procedure in Synthesis Example 1, by using 4-amino-2-chlorophenol (3.00 g, 19.6 mmole), DMF (80 ml), TEA (0.5 ml), and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (1.40 g, 8.36 mmole), 2.00 g (76.0% yield) of 2-chloro-5-(2,3,5,6-tetrafluoro-4-methylbenzylamino)phenol was obtained as a y... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Aromatic halide.Primary halide.Aromatic alcohol.Primary amine | Aromatic halide.Aromatic alcohol.Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br- | null | null | null | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(O)c(Cl)c1>>Cc1c(F)c(F)c(CNc2ccc(Cl)c(O)c2)c(F)c1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-66851f08c5224104813f8dba4d0abb62 | NC(=O)c1cc(N(Cc2c(F)c(F)c(C(F)(F)F)c(F)c2F)C(=O)C(F)(F)F)ccc1OC(=O)C(F)(F)F>>NC(=O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1O | FC(C(=O)OC1=C(C=C(C=C1)N(C(C(F)(F)F)=O)CC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F)C(N)=O)(F)F>>OC1=C(C(=O)N)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F | O=C(C(F)(F)F)[N:7]([c:6]1[cH:5][c:4]([C:2]([NH2:1])=[O:3])[c:25]([O:26]C(=O)C(F)(F)F)[cH:24][cH:23]1)[CH2:8][c:9]1[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17])[F:18])[c:19]([F:20])[c:21]1[F:22]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([NH:7][CH2:8][c:9]2[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17]... | NC(=O)c1cc(N(Cc2c(F)c(F)c(C(F)(F)F)c(F)c2F)C(=O)C(F)(F)F)ccc1OC(=O)C(F)(F)F | NC(=O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1O | null | null | O.CO | Reduction | OtherReaction | e732b2e4043397b4d449cd428dab168843bdc776f00bc9fc33f856fcf51f73d9 | 7306b7444ac76569af96bfc353474db991eabf13620e7820935e2aec88c27ee1 | c1ccc(CNc2ccccc2)cc1 | F-C(-F)(-F)-C(=O)-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5](-[N;H0;D3;+0:6](-[C:7]-[c:8])-C(=O)-C(-F)(-F)-F):[c:9]:[c:10]:1-[C:11](-[N;D1;H2:12])=[O;D1;H0:13]>>[N;D1;H2:12]-[C:11](=[O;D1;H0:13])-[c:10]1:[c:9]:[c:5](-[NH;D2;+0:6]-[C:7]-[c:8]):[c:4]:[c:3]:[c:2]:1-[OH;D1;+0:1] | 60.4 | [{"value": 60.0, "product": "OC1=C(C(=O)N)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.4, "product": "OC1=C(C(=O)N)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 2-carbamoyl-4-[2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl-(2,2,2-trifluoroacetyl)amino]phenyl trifluoroacetate (300 mg, 0.52 mmole) in methanol (8 ml) and water (3 ml) was added c-HCl (2.0 ml) at 40° C. under a nitrogen atmosphere. After the reaction mixture was stirred for 24 hr, the organic solvent ... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Trifluoro group.Ester.Tertiary amide | Aromatic alcohol.Secondary amine | null | null | c1ccccc1.c1ccccc1 | Other | O.CO | null | 24 | NC(=O)c1cc(N(Cc2c(F)c(F)c(C(F)(F)F)c(F)c2F)C(=O)C(F)(F)F)ccc1OC(=O)C(F)(F)F>O.CO>NC(=O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e4fa4aa1191e49bdb2e5eef8bfebf1e1 | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(S(=O)(=O)O)c(O)c1>>O=S(=O)(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1O | CN(C)C=O.NC1=CC(=C(C=C1)S(=O)(=O)O)O.FC1=C(CBr)C(=C(C(=C1F)C(F)(F)F)F)F>>OC1=C(C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F)S(=O)(=O)O | Br[CH2:9][c:10]1[c:11]([F:12])[c:13]([F:14])[c:15]([C:16]([F:17])([F:18])[F:19])[c:20]([F:21])[c:22]1[F:23].[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:25][cH:24][c:7]([NH2:8])[cH:6][c:26]1[OH:27]>>[O:1]=[S:2](=[O:3])([OH:4])[c:5]1[cH:6][c:7]([NH:8][CH2:9][c:10]2[c:11]([F:12])[c:13]([F:14])[c:15]([C:16]([F:17])([F:18])[F:19])... | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(S(=O)(=O)O)c(O)c1 | O=S(=O)(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | fb14e376a8ea411d1b814ae4d8f85eb9e6fad53469f2e0ef9107e3c147574d24 | 7f961f9f63fb19401b9cb6ccb23b7f9357060620e96238b4ca2454442616e763 | c1ccc(CNc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6]1:[c:7]:[cH;D2;+0:8]:[c;H0;D3;+0:9](-[#16:10](=[O;D1;H0:11])(=[O;D1;H0:12])-[O;D1;H1:13]):[c;H0;D3;+0:14](-[O;D1;H1:15]):[cH;D2;+0:16]:1>>[O;D1;H0:11]=[#16:10](=[O;D1;H0:12])(-[O;D1;H1:13])-[c;H0;D3;+0:9]1:[cH;D2;+0:16]:[c:6](-[NH;D2;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:... | 28 | [{"value": 28.0, "product": "OC1=C(C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F)S(=O)(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the similar procedure in Synthesis Example 1, by using 4-amino-2-hydroxybenzene sulfonic acid (1.00 g, 5.30 mmole), DMF (10 ml), TEA (1.0 ml), and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (0.88 g, 5.30 mmole), 0.61 g (28.0% yield) of 2-hydroxy-5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol.Primary amine | Aromatic alcohol.Secondary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HBr | null | null | null | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(S(=O)(=O)O)c(O)c1>>O=S(=O)(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-43cc6966ac17402492f3a6f82d958b8e | CO.Nc1ccc(O)c(C(=O)O)c1>>COC(=O)c1cc(N)ccc1O | NC1=CC=C(C(C(=O)O)=C1)O.CO>>NC=1C=CC(=C(C(=O)OC)C1)O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:9][cH:10][c:11]1[OH:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:9][cH:10][c:11]1[OH:12] | CO.Nc1ccc(O)c(C(=O)O)c1 | COC(=O)c1cc(N)ccc1O | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 76 | [{"value": 76.0, "product": "NC=1C=CC(=C(C(=O)OC)C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 5-aminosalicylic acid (3.00 g, 19.6 mmole) in methanol (80 ml) was added c-H2SO4 (8 ml) at 0° C. After the reaction mixture was refluxed for 6 hr, the solvent was removed in vacuo. The resulting residue was partitioned with ethyl acetate and water. The organic layer was washed with water (40 ml×3) and ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.Nc1ccc(O)c(C(=O)O)c1>>COC(=O)c1cc(N)ccc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-83e2a5dadaef4015baabb40fa38b9712 | CC(=O)Cl.CC(C)(C)OC(=O)Nc1ccc(O)c(C(=O)O)c1>>CC(=O)Oc1ccc(NC(=O)OC(C)(C)C)cc1C(=O)O | C(C)(C)(C)OC(=O)NC=1C=CC(=C(C(=O)O)C1)O.C(C)(=O)Cl.C([O-])([O-])=O.[K+].[K+]>>C(C)(=O)OC1=C(C(=O)O)C=C(C=C1)NC(=O)OC(C)(C)C | Cl[C:2]([CH3:1])=[O:3].[OH:4][c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][c:18]1[C:19](=[O:20])[OH:21]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([NH:9][C:10](=[O:11])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][c:18]1[C:19](=[O:20])[OH:21] | CC(=O)Cl.CC(C)(C)OC(=O)Nc1ccc(O)c(C(=O)O)c1 | CC(=O)Oc1ccc(NC(=O)OC(C)(C)C)cc1C(=O)O | null | null | CN(C)C=O | Acylation | Schotten-Baumann to ester | 1cda078f55e64d9385e544d1067595d5e7672bbd1eff542e7a341817a2d8c4d5 | 6439fc27f97ee9ed7c11ef9b5032d9493d05f28a7bbb50d256a2d54d035fbfb2 | c1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5](-[O;D1;H1:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:9]-[c:8](:[c:10]):[c:7]-[C:5](=[O;D1;H0:4])-[O;D1;H1:6] | 52.2 | [{"value": 52.0, "product": "C(C)(=O)OC1=C(C(=O)O)C=C(C=C1)NC(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 52.2, "product": "C(C)(=O)OC1=C(C(=O)O)C=C(C=C1)NC(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a solution of 5-tert-butoxycarbonylamino-2-hydroxybenzoic acid (1.02 g, 4.02 mmole) in DMF (20.0 ml) was added with acetyl chloride (39 mg, 4.83 mmole) and potassium carbonate (555 mg, 4.02 mmole). The reaction mixture was stirred for 4 hr at room temperature. After the reaction mixture was concentrated, the residue... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Ester | null | null | c1ccccc1 | HCl | CN(C)C=O | null | 4 | CC(=O)Cl.CC(C)(C)OC(=O)Nc1ccc(O)c(C(=O)O)c1>CN(C)C=O>CC(=O)Oc1ccc(NC(=O)OC(C)(C)C)cc1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f99c4245f5024eafbed92d5ba276e740 | CC(=O)Oc1ccc(NC(=O)OC(C)(C)C)cc1C(=O)O>>CC(=O)Oc1ccc(N)cc1C(=O)O | C(C)(=O)OC1=C(C(=O)O)C=C(C=C1)NC(=O)OC(C)(C)C>>C(C)(=O)OC1=C(C(=O)O)C=C(C=C1)N | CC(C)(C)OC(=O)[NH:9][c:8]1[cH:7][cH:6][c:5]([O:4][C:2]([CH3:1])=[O:3])[c:11]([C:12](=[O:13])[OH:14])[cH:10]1>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:10][c:11]1[C:12](=[O:13])[OH:14] | CC(=O)Oc1ccc(NC(=O)OC(C)(C)C)cc1C(=O)O | CC(=O)Oc1ccc(N)cc1C(=O)O | null | null | C(=O)(C(F)(F)F)O.C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 97.4 | [{"value": 97.0, "product": "C(C)(=O)OC1=C(C(=O)O)C=C(C=C1)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.4, "product": "C(C)(=O)OC1=C(C(=O)O)C=C(C=C1)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | The mixture of 2-ethanoyloxy-5-tert-butoxycarbonylaminobenzoic acid (1.01 g, 3.42 mmole) in TFA/CH2Cl2 (20.0 ml. 1:1 v/v) was stirred for 30 min at room temperature. After the reaction mixture was concentrated, the residue was dissolved in ether. The resulting residue was recrystallized from ethyl acetate/hexane to giv... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1 | HO- | C(=O)(C(F)(F)F)O.C(Cl)Cl | null | 0.5 | CC(=O)Oc1ccc(NC(=O)OC(C)(C)C)cc1C(=O)O>C(=O)(C(F)(F)F)O.C(Cl)Cl>CC(=O)Oc1ccc(N)cc1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4064f24c2f454f90b18ac8aeebb5accc | CC(=O)Oc1ccc(N)cc1C(=O)O.Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr>>CC(=O)Oc1ccc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)cc1C(=O)O | C(C)(=O)OC1=C(C(=O)O)C=C(C=C1)N.FC1=C(CBr)C(=C(C(=C1F)C(F)(F)F)F)F>>C(C)(=O)OC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F | [CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([NH2:9])[cH:25][c:26]1[C:27](=[O:28])[OH:29].Br[CH2:10][c:11]1[c:12]([F:13])[c:14]([F:15])[c:16]([C:17]([F:18])([F:19])[F:20])[c:21]([F:22])[c:23]1[F:24]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][cH:7][c:8]([NH:9][CH2:10][c:11]2[c:12]([F:13])[c:14]([F:15])[c:16]([C:17]([F:1... | CC(=O)Oc1ccc(N)cc1C(=O)O.Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr | CC(=O)Oc1ccc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)cc1C(=O)O | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 53 | [{"value": 53.0, "product": "C(C)(=O)OC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the similar procedure in Synthesis Example 1, by using 2-ethanoyloxy-5-aminobenzoic acid (0.81 g, 4.10 mmole) which was prepared from Synthesis Example (14-3), DMF (15 ml), TEA (0.1 ml), tetrabutyl ammonium iodide (5 mg), and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (1.02 ml, 6.15 mmole), 0.92 g... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HBr | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O | null | null | CC(=O)Oc1ccc(N)cc1C(=O)O.Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O>CC(=O)Oc1ccc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)cc1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1bc26572ee124f468997dceac639fc1f | CCC(=O)Oc1ccc(N)cc1C(=O)O.Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr>>CCC(=O)Oc1ccc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)cc1C(=O)O | NC=1C=CC(=C(C(=O)O)C1)OC(CC)=O.FC1=C(CBr)C(=C(C(=C1F)C(F)(F)F)F)F>>C(CC)(=O)OC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F | [CH3:1][CH2:2][C:3](=[O:4])[O:5][c:6]1[cH:7][cH:8][c:9]([NH2:10])[cH:26][c:27]1[C:28](=[O:29])[OH:30].Br[CH2:11][c:12]1[c:13]([F:14])[c:15]([F:16])[c:17]([C:18]([F:19])([F:20])[F:21])[c:22]([F:23])[c:24]1[F:25]>>[CH3:1][CH2:2][C:3](=[O:4])[O:5][c:6]1[cH:7][cH:8][c:9]([NH:10][CH2:11][c:12]2[c:13]([F:14])[c:15]([F:16])[c... | CCC(=O)Oc1ccc(N)cc1C(=O)O.Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr | CCC(=O)Oc1ccc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)cc1C(=O)O | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | c1ccc(CNc2ccccc2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 51 | [{"value": 51.0, "product": "C(CC)(=O)OC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the similar procedure in Synthesis Example 14-4, by using 5-amino-2-propanoyloxybenzoic acid (0.32 g, 1.53 mmole) which was prepared from Synthesis Example (15-2), DMF (10 ml), TEA (0.05 ml), tetrabutyl ammonium iodide (3 mg), and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (0.38 ml, 2.30 mmole), 0... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1 | HBr | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O | null | null | CCC(=O)Oc1ccc(N)cc1C(=O)O.Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O>CCC(=O)Oc1ccc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)cc1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae901311a46d4e2eb7b0e3a82f66843e | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(OC(=O)C2CCCCC2)c(C(=O)O)c1>>O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1OC(=O)C1CCCCC1 | NC=1C=CC(=C(C(=O)O)C1)OC(=O)C1CCCCC1.FC1=C(CBr)C(=C(C(=C1F)C(F)(F)F)F)F>>C1(CCCCC1)C(=O)OC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F | Br[CH2:8][c:9]1[c:10]([F:11])[c:12]([F:13])[c:14]([C:15]([F:16])([F:17])[F:18])[c:19]([F:20])[c:21]1[F:22].[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH2:7])[cH:23][cH:24][c:25]1[O:26][C:27](=[O:28])[CH:29]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6]([NH:7][CH2:8][c:9]2[c:10]([F:11])[c:12... | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(OC(=O)C2CCCCC2)c(C(=O)O)c1 | O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1OC(=O)C1CCCCC1 | null | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | fc19a1445ff204e66e51735d0191465bda3c6691fd233624a54742c9d4828411 | 0b1d32f56ad00f1e5bdae9390f9227bbea012fa2f8203aac34726b8a6761cc7c | O=C(Oc1ccc(NCc2ccccc2)cc1)C1CCCCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[CH2;D2;+0:1]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 49 | [{"value": 49.0, "product": "C1(CCCCC1)C(=O)OC1=C(C(=O)O)C=C(C=C1)NCC1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | According to the similar procedure in Synthesis Example (14-4), by using 5-amino-2-cyclohexanecarbonyloxybenzoic acid (1.03 g, 3.95 mmole) which was prepared from Synthesis Example (16-2), DMF (15 ml), TEA (0.10 ml), tetrabutyl ammonium iodide (10 mg), and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (1.01 ml, 5... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amine | Secondary amine | null | null | c1ccccc1.c1ccccc1.C1CCCCC1 | HBr | [I-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O | null | null | Fc1c(F)c(C(F)(F)F)c(F)c(F)c1CBr.Nc1ccc(OC(=O)C2CCCCC2)c(C(=O)O)c1>[I-].C(CCC)[N+](CCCC)(CCCC)CCCC.CN(C)C=O>O=C(O)c1cc(NCc2c(F)c(F)c(C(F)(F)F)c(F)c2F)ccc1OC(=O)C1CCCCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a2f5b3af7a1a425d85bfd0a6f9b274fa | CC(C)(C)OC(=O)Nc1cccnc1.O=C=Nc1ccc(Cl)cc1>>CC(C)(C)OC(=O)Nc1cnccc1C(=O)Nc1ccc(Cl)cc1 | C(C)(C)(C)OC(=O)NC=1C=NC=CC1.[Li]C(C)(C)C.ClC1=CC=C(C=C1)N=C=O>>C(C)(C)(C)OC(=O)NC=1C=NC=CC1C(=O)NC1=CC=C(C=C1)Cl | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][n:11][cH:12][cH:13][cH:14]1.[C:15](=[O:16])=[N:17][c:18]1[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][c:9]1[cH:10][n:11][cH:12][cH:13][c:14]1[C:15](=[O:16])[NH:17][c:18]1[cH:19][cH:20][c:21]([Cl:2... | CC(C)(C)OC(=O)Nc1cccnc1.O=C=Nc1ccc(Cl)cc1 | CC(C)(C)OC(=O)Nc1cnccc1C(=O)Nc1ccc(Cl)cc1 | null | null | C1CCOC1 | Acylation | OtherReaction | 83e204f94d06c21a57e066d9b0f22fdad61493b015559d3b3ec187461ef75bb8 | 3347203d95f451dc113645420a6f5b484c71b9ef5d3ed902199ccd8a70632b86 | O=C(Nc1ccccc1)c1ccncc1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[c:9]1:[c:10]:[#7;a:11]:[c:12]:[c:13]:[cH;D2;+0:14]:1.[O;D1;H0:15]=[C;H0;D2;+0:16]=[N;H0;D2;+0:17]-[c:18](:[c:19]):[c:20]>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[#8:5]-[C:6](=[O;D1;H0:7])-[#7:8]-[c:9]1:[c:10]:[#7;a:11]:[c:12]:[c:13]... | 36 | [{"value": 36.0, "product": "C(C)(C)(C)OC(=O)NC=1C=NC=CC1C(=O)NC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.8, "product": "C(C)(C)(C)OC(=O)NC=1C=NC=CC1C(=O)NC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -30 | CELSIUS | 1 | HOUR | The 3-tert-butoxycarbonylaminopyridine (2.0035 g, 10.32 mmol) was dissolved in THF (100 mL). The solution was cooled to −30° C. in a dry ice/acetonitrile bath, then t-BuLi (13 mL, 22.1 mmol) was added dropwise. After 1 h, 4-chlorophenyl isocyanate (1.911 g, 12.44 mmol) was added. The reaction mixture was warmed to 0° C... | 10.6084/m9.figshare.5104873.v1 | null | Isocyanate | Secondary amide | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | null | C1CCOC1 | -30 | 1 | CC(C)(C)OC(=O)Nc1cccnc1.O=C=Nc1ccc(Cl)cc1>C1CCOC1>CC(C)(C)OC(=O)Nc1cnccc1C(=O)Nc1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3c0ec90aa0e64da095384d499776ad82 | CC(C)(C)OC(=O)Nc1cnccc1C(=O)Nc1ccc(Cl)cc1>>Nc1cnccc1C(=O)Nc1ccc(Cl)cc1 | C(C)(C)(C)OC(=O)NC=1C=NC=CC1C(=O)NC1=CC=C(C=C1)Cl.FC(C(=O)O)(F)F>>NC=1C=NC=CC1C(=O)NC1=CC=C(C=C1)Cl | CC(C)(C)OC(=O)[NH:1][c:2]1[cH:3][n:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1>>[NH2:1][c:2]1[cH:3][n:4][cH:5][cH:6][c:7]1[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][c:14]([Cl:15])[cH:16][cH:17]1 | CC(C)(C)OC(=O)Nc1cnccc1C(=O)Nc1ccc(Cl)cc1 | Nc1cnccc1C(=O)Nc1ccc(Cl)cc1 | null | null | null | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(Nc1ccccc1)c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2](:[c:3]:[#7;a:4]:[c:5]):[c:6]-[C:7](-[#7:8])=[O;D1;H0:9]>>[#7:8]-[C:7](=[O;D1;H0:9])-[c:6]:[c:2](-[NH2;D1;+0:1]):[c:3]:[#7;a:4]:[c:5] | 93.2 | [{"value": 93.0, "product": "NC=1C=NC=CC1C(=O)NC1=CC=C(C=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 93.2, "product": "NC=1C=NC=CC1C(=O)NC1=CC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 10 | MINUTE | To 3-(N-tert-butoxycarbonylamino)-N-(4-chlorophenyl)-pyridine-4-carboxamide (552 mg, 1.59 mmol) was added trifluoroacetic acid (3 mL, 38.95 mmol). After stirring for 10 min, the reaction mixture was concentrated, diluted with CH2Cl2, washed with satd Na2CO3, dried (Na2SO4) and concentrated to give the title compound (3... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccncc1.c1ccccc1 | HO- | null | null | 0.166667 | CC(C)(C)OC(=O)Nc1cnccc1C(=O)Nc1ccc(Cl)cc1>>Nc1cnccc1C(=O)Nc1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72635546d05941bc89539332989fdc4d | C[Si](C)(C)C=[N+]=[N-].O=C(O)c1ccc(F)cc1O>>COC(=O)c1ccc(F)cc1O | C[Si](C)(C)C=[N+]=[N-].FC1=CC(=C(C(=O)O)C=C1)O.CCCCCC.C[Si](C)(C)C=[N+]=[N-]>>FC1=CC(=C(C(=O)OC)C=C1)O | C[Si](C)(C)[CH:1]=[N+]=[N-].[OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[OH:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[OH:12] | C[Si](C)(C)C=[N+]=[N-].O=C(O)c1ccc(F)cc1O | COC(=O)c1ccc(F)cc1O | null | null | C1=CC=CC=C1.CO | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 39589be0e9a30df66714fe618d22a8ac0fb24901dbf2ead1ab33e31556c7ac64 | 8b539baf7aeb5ab868833e33306bad77200a853d562904197e13de2e27e229d7 | c1ccccc1 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].[O;D1;H0:2]=[C:3](-[OH;D1;+0:4])-[c:5]>>[CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3](=[O;D1;H0:2])-[c:5] | 98 | [{"value": 98.0, "product": "FC1=CC(=C(C(=O)OC)C=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A solution of 4-fluoro-2-hydroxybenzoic acid (9.8 g, 62.3 mmol) in benzene (100 mL) and MeOH (20 mL) was cooled in an ice bath and a 2 M hexane solution of (trimethyl-silyl)diazomethane (50 mL) was added dropwise. The reaction was stirred overnight at ambient temperature, diluted with benzene (348 mL) and MeOH (39 mL),... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo.Silyl protective group | Ester | null | null | c1ccccc1 | Other | C1=CC=CC=C1.CO | null | 8 | C[Si](C)(C)C=[N+]=[N-].O=C(O)c1ccc(F)cc1O>C1=CC=CC=C1.CO>COC(=O)c1ccc(F)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b54b93e44bc459fb114f8396288f7b7 | CC(C)(C)OC(=O)N1CCC(O)CC1.COC(=O)c1ccc(F)cc1O>>COC(=O)c1ccc(F)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | N(=NC(=O)OCC)C(=O)OCC.FC1=CC(=C(C(=O)OC)C=C1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(C)(C)OC(=O)N1CCC(CC1)O>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)F | O[CH:13]1[CH2:14][CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH2:24][CH2:25]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[OH:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[O:12][CH:13]1[CH2:14][CH2:15][N:16]([C:17](=[O:18])[O:19][C:20]([C... | CC(C)(C)OC(=O)N1CCC(O)CC1.COC(=O)c1ccc(F)cc1O | COC(=O)c1ccc(F)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | C1=CC=CC=C1.C(Cl)Cl | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | a9e936b0e9135225700edbab1c7696738b7f1f0756494b6ceeeda63b184d572f | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1ccc(OC2CCNCC2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[O;H0;D2;+0:12]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:13] | 61 | [{"value": 61.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60.8, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A mixture of methyl 4-fluoro-2-hydroxybenzoate (5.1 g, 30 mmol), triphenylphosphine (9.5 g, 36 mmol), 1-tert-butoxycarbonyl-4-hydroxypiperidine (6 g, 30 mmol), and benzene (10 mL) was heated until all solids dissolved. The solution was cooled to 0° C., then sonicated while adding diethyl azodicarboxylate (6.3 g, 36 mmo... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HO- | C1=CC=CC=C1.C(Cl)Cl | 0 | null | CC(C)(C)OC(=O)N1CCC(O)CC1.COC(=O)c1ccc(F)cc1O>C1=CC=CC=C1.C(Cl)Cl>COC(=O)c1ccc(F)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-474ff65ba61c420db473efdf7d92bd68 | C1CCNC1.COC(=O)c1ccc(F)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>>COC(=O)c1ccc(N2CCCC2)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)F.N1CCCC1>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)N1CCCC1 | [NH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1.F[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:15]([O:16][CH:17]2[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]2)[cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)[cH:14][c:1... | C1CCNC1.COC(=O)c1ccc(F)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | COC(=O)c1ccc(N2CCCC2)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | 389dbc6c760ba22d5b089335787069e4da1dc4ed4889d745a0e1de1824c34c09 | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1cc(OC2CCNCC2)cc(N2CCCC2)c1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[C:6]1-[C:7]-[C:8]-[C:9]-[NH;D2;+0:10]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:10]1-[C:6]-[C:7]-[C:8]-[C:9]-1):[c:4]:[c:5] | 282.8 | [{"value": 100.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)N1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 282.8, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)N1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | 3 | HOUR | The methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoate (7.99 mmol, 22.6 mmol) was diluted with pyrrolidine (18 mL, 215.6 mmol). The resulting mixture was heated to 80° C. After 3 h, the reaction mixture was cooled to room temperature and quenched with water (50 mL). The mixture was extracted with dichlo... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1CCNC1.c1ccccc1 | c1ccccc1.C1CC[NH]C1 | c1ccccc1.C1CC[NH]C1.C1CC[NH]CC1 | HF | null | 80 | 3 | C1CCNC1.COC(=O)c1ccc(F)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>>COC(=O)c1ccc(N2CCCC2)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c19dc6be78b24ac5b520a14c933ce49f | COC(=O)c1ccc(N2CCCC2)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>>CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)O)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)N1CCCC1.[Li+].[OH-].CO>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)O)C=CC(=C1)N1CCCC1 | C[O:26][C:24]([c:23]1[c:13]([O:12][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:28][CH2:27]2)[cH:14][c:15]([N:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[cH:21][cH:22]1)=[O:25]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][c:15]([N:16]... | COC(=O)c1ccc(N2CCCC2)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)O)CC1 | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1cc(OC2CCNCC2)cc(N2CCCC2)c1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 78.2 | [{"value": 78.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)O)C=CC(=C1)N1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.2, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)O)C=CC(=C1)N1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A mixture of methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoate (9.133 g, 22.6 mmol), 1 M LiOH (40 mL, 40 mmol), MeOH (30 mL) and THF (90 mL) was heated at 60° C. for 14 h. The reaction mixture was concentrated to one-third of its initial volume, diluted with EtOAc (700 mL), and washed with s... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]CC1.c1ccccc1.C1CC[NH]C1 | Other | C1CCOC1 | 60 | null | COC(=O)c1ccc(N2CCCC2)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>C1CCOC1>CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d389d159301e4655a135a97230471e10 | COC(=O)c1ccc(F)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>>CC(C)(C)OC(=O)N1CCC(Oc2cc(F)ccc2C(=O)O)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)F.[Li+].[OH-].CO.C1CCOC1>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)O)C=CC(=C1)F | C[O:22][C:20]([c:19]1[c:13]([O:12][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:24][CH2:23]2)[cH:14][c:15]([F:16])[cH:17][cH:18]1)=[O:21]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][c:15]([F:16])[cH:17][cH:18][c:19]2[C:20](=[O:2... | COC(=O)c1ccc(F)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | CC(C)(C)OC(=O)N1CCC(Oc2cc(F)ccc2C(=O)O)CC1 | null | null | CCOC(=O)C | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(OC2CCNCC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 76.1 | [{"value": 76.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)O)C=CC(=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.1, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)O)C=CC(=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoate (3.05 g, 8.64 mmol), 1 M aq LiOH (15 mL, 15 mmol), MeOH (15 mL), and THF (45 mL) was stirred overnight. The reaction mixture was diluted with EtOAc, washed with satd citric acid, dried over MgSO4, concentrated, and triturated with ether to ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]CC1.c1ccccc1 | Other | CCOC(=O)C | null | 8 | COC(=O)c1ccc(F)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>CCOC(=O)C>CC(C)(C)OC(=O)N1CCC(Oc2cc(F)ccc2C(=O)O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-503ed7f5676548619595cdfb9337a1fe | CC(C)(C)OC(=O)N1CCC(O)CC1.COC(=O)c1ccc(C(C)(C)C)cc1O>>COC(=O)c1ccc(C(C)(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | N(=NC(=O)OC(C)C)C(=O)OC(C)C.C(C)(C)(C)C1=CC(=C(C(=O)OC)C=C1)O.C(=O)(OC(C)(C)C)N1CCC(CC1)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)(C)(C)C1=CC(=C(C(=O)OC)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C | O[CH:16]1[CH2:17][CH2:18][N:19]([C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:27][CH2:28]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][c:14]1[OH:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][c:14]1[O:15][CH:1... | CC(C)(C)OC(=O)N1CCC(O)CC1.COC(=O)c1ccc(C(C)(C)C)cc1O | COC(=O)c1ccc(C(C)(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | a9e936b0e9135225700edbab1c7696738b7f1f0756494b6ceeeda63b184d572f | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1ccc(OC2CCNCC2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[O;H0;D2;+0:12]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:13] | null | [] | null | null | 72 | HOUR | To a stirring solution of methyl 4-tert-butyl-2-hydroxybenzoate (9.45 g, 45.4 mmol), 1-Boc-piperidin-4-ol (9.6 g, 47.7 mmol) and triphenylphosphine (12.5 g, 47.7 mmol) in THF (125 mL) was added, dropwise via an addition funnel, a solution of diisopropyl azodicarboxylate (9.4 mL, 47.7 mmol) in THF (25 mL). After 72 h, t... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HO- | C1CCOC1 | null | 72 | CC(C)(C)OC(=O)N1CCC(O)CC1.COC(=O)c1ccc(C(C)(C)C)cc1O>C1CCOC1>COC(=O)c1ccc(C(C)(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f322c29aeb1e485caf31e657dd35d2b8 | COC(=O)c1ccc(C(C)(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>>CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)O)CC1 | C(C)(C)(C)C1=CC(=C(C(=O)OC)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C.O[Li].O>>C(C)(C)(C)C1=CC(=C(C(=O)O)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C | C[O:25][C:23]([c:22]1[c:13]([O:12][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:27][CH2:26]2)[cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]1)=[O:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][c:15]([C:16]([CH3:... | COC(=O)c1ccc(C(C)(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)O)CC1 | null | null | O1CCOCC1.O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(OC2CCNCC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 91 | [{"value": 91.0, "product": "C(C)(C)(C)C1=CC(=C(C(=O)O)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.7, "product": "C(C)(C)(C)C1=CC(=C(C(=O)O)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirring solution of methyl 4-(tert-butyl)-2-(1-Boc-piperidin-4-yloxy)benzoate (12.9 g, 33 mmol) in p-dioxane (150 mL) was added a solution of LiOH hydrate (2.8 g, 66 mmol) in water (75 mL). The next morning, the solvent was removed in vacuo, and the residue was diluted with water (200 mL) and washed with diethyl ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]CC1.c1ccccc1 | Other | O1CCOCC1.O | null | null | COC(=O)c1ccc(C(C)(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>O1CCOCC1.O>CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2824e47e2c2d4ebf8986ba5d92c2c82d | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)O)CC1.Nc1cccnc1C(=O)Nc1ccc(Cl)cn1.O=C([O-])C(F)(F)F>>CC(C)(C)c1ccc(C(=O)Nc2cccnc2C(=O)Nc2ccc(Cl)cn2)c(OC2CCNCC2)c1.O=C(O)C(F)(F)F | NC=1C(=NC=CC1)C(=O)NC1=NC=C(C=C1)Cl.C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)O)C=CC(=C1)C(C)(C)C.FC(C(=O)[O-])(F)F>>FC(C(=O)O)(F)F.C(C)(C)(C)C1=CC(=C(C(=O)NC=2C(=NC=CC2)C(=O)NC2=NC=C(C=C2)Cl)C=C1)OC1CCNCC1 | CC(C)(C)OC(=O)[N:33]1[CH2:32][CH2:31][CH:30]([O:29][c:28]2[c:8]([C:9](O)=[O:10])[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:36]2)[CH2:35][CH2:34]1.[NH2:11][c:12]1[cH:13][cH:14][cH:15][n:16][c:17]1[C:18](=[O:19])[NH:20][c:21]1[cH:22][cH:23][c:24]([Cl:25])[cH:26][n:27]1.[O:37]=[C:38]([O-:39])[C:40]([F:41])([F:42... | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)O)CC1.Nc1cccnc1C(=O)Nc1ccc(Cl)cn1.O=C([O-])C(F)(F)F | CC(C)(C)c1ccc(C(=O)Nc2cccnc2C(=O)Nc2ccc(Cl)cn2)c(OC2CCNCC2)c1.O=C(O)C(F)(F)F | null | null | null | Protection | OtherReaction | 7b8bd0a5903e8e7c9e6eb0e6d81e832fb78e2f9a7f8a1a8ebe542a80dfd09347 | 56cbaae9039b7a3d35974b4340a6737b25f33de7957a48106ebbad7a8d9a3713 | O=C(Nc1cccnc1C(=O)Nc1ccccn1)c1ccccc1OC1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].O-[C;H0;D3;+0:6](=[O;D1;H0:7])-[c:8](:[c:9]):[c:10].[#7:11]-[C:12](=[O;D1;H0:13])-[c:14](:[#7;a:15]:[c:16]):[c:17](-[NH2;D1;+0:18]):[c:19].[F;D1;H0:20]-[C:21](-[F;D1;H0:22])(-[F;D1;H0:23])-[C:24](-[O-;H0;D1:25])=[O;D1;H0:26]>>[#7:11]-[C:12](=[O;D1;H0:13])-[c:... | 30 | [{"value": 30.0, "product": "FC(C(=O)O)(F)F.C(C)(C)(C)C1=CC(=C(C(=O)NC=2C(=NC=CC2)C(=O)NC2=NC=C(C=C2)Cl)C=C1)OC1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using methods substantially equivalent to those described in Example 1-I, 3-amino-N-(5-chloropyridin-2-yl)-pyridine-2-carboxamide (626 mg, 2.52 mmol) and 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-tert-butylbenzoic acid (500 mg, 1.47 mmol) yielded, after deprotection of the coupled product using methods substantially... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Carboxylic acid.Secondary amide.Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.c1ccncc1.c1ccncc1.C1CCNCC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)O)CC1.Nc1cccnc1C(=O)Nc1ccc(Cl)cn1.O=C([O-])C(F)(F)F>>CC(C)(C)c1ccc(C(=O)Nc2cccnc2C(=O)Nc2ccc(Cl)cn2)c(OC2CCNCC2)c1.O=C(O)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5725c0e56974409fad22d836a0ede21a | CO.COCOc1cc(C(C)(C)C)ccc1C(=O)O>>COC(=O)c1ccc(C(C)(C)C)cc1O | C(C)(C)(C)C1=CC(=C(C(=O)O)C=C1)OCOC.CO>>C(C)(C)(C)C1=CC(=C(C(=O)OC)C=C1)O | O[CH3:1].COC[O:15][c:14]1[c:5]([C:3]([OH:2])=[O:4])[cH:6][cH:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([C:9]([CH3:10])([CH3:11])[CH3:12])[cH:13][c:14]1[OH:15] | CO.COCOc1cc(C(C)(C)C)ccc1C(=O)O | COC(=O)c1ccc(C(C)(C)C)cc1O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | d91c443ba57fb40e0967883daa0187a51b2b8803be256f291442bd62ce559ed9 | a908e90609f639256990fb4c36be9ac4315f79d646aca954876e9a637ca9dd82 | c1ccccc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7].O-[CH3;D1;+0:8]>>[CH3;D1;+0:8]-[O;H0;D2;+0:7]-[C:5](=[O;D1;H0:6])-[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | null | [] | null | null | null | null | A solution of 4-tert-butyl-2-(methoxymethoxy)benzoic acid (61.80 g, 259 mmol) and MeOH (865 mL) was cooled in an ice bath. Gaseous HCl was sparged through the cold fluid for 30 min to saturate it, and the solution was then heated to reflux. A Soxhlet extractor containing 3 Å molecular sieves was used to absorb the wate... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether.Methanol | Ester.Aromatic alcohol | null | null | c1ccccc1 | HO- | null | null | null | CO.COCOc1cc(C(C)(C)C)ccc1C(=O)O>>COC(=O)c1ccc(C(C)(C)C)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-47b76ad718ce4b32b774f444c4c5d7a8 | CC(C)c1cccc(O)c1.COCCl>>COCOc1cccc(C(C)C)c1 | C(C)(C)C=1C=C(C=CC1)O.C(C)(C)N(CC)C(C)C.COCCl>>C(C)(C)C1=CC(=CC=C1)OCOC | [OH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([CH:10]([CH3:11])[CH3:12])[cH:13]1.Cl[CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9]([CH:10]([CH3:11])[CH3:12])[cH:13]1 | CC(C)c1cccc(O)c1.COCCl | COCOc1cccc(C(C)C)c1 | null | null | O.C(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 6e90ffbf0683e1a3ee55c5e3ea453aefc5ddd369c0150ed0150f9546d7e47f4f | efd670663709b79afcad1306da9f69b33a0147cfa3639ca4c0b54b35ef4b1852 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:3]-[#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 56 | [{"value": 56.0, "product": "C(C)(C)C1=CC(=CC=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.5, "product": "C(C)(C)C1=CC(=CC=C1)OCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | Into methylene chloride (300 mL) was dissolved 3-isopropylphenol (27.24 g, 200 mmol). After cooling the solution in an ice bath, diisopropylethyl amine (69.7 mL, 400 mmol) was added in one portion, followed by the dropwise addition of chloromethyl methyl ether (18.9 mL, 236 mmol) in methylene chloride (50 mL). The reac... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol | Ether.Ether | null | null | c1ccccc1 | HCl | O.C(Cl)Cl | null | 16 | CC(C)c1cccc(O)c1.COCCl>O.C(Cl)Cl>COCOc1cccc(C(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-34d6ef1d399e470fa61f10610c2eca38 | COCOc1cc(C(C)C)ccc1C(=O)O>>COC(=O)c1ccc(C(C)C)cc1O | C[Si](C)(C)C=[N+]=[N-].C(C)(=O)Cl.C(C)(C)C1=CC(=C(C(=O)O)C=C1)OCOC.Cl>>C(C)(C)C1=CC(=C(C(=O)OC)C=C1)O | C(O[CH3:1])[O:14][c:13]1[c:5]([C:3]([OH:2])=[O:4])[cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[cH:12]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[cH:12][c:13]1[OH:14] | COCOc1cc(C(C)C)ccc1C(=O)O | COC(=O)c1ccc(C(C)C)cc1O | null | null | CCCCCC.C(Cl)Cl.CO | Miscellaneous | OtherReaction | 63e23a9fe2462a14c98b1466cfbe5f3f59528d6fd75acfa2a84c440daa67b1ed | 07b207b90c7119940291c3edd7051bccfd65e305571c0c76ed1431969e2388d0 | c1ccccc1 | [CH3;D1;+0:1]-O-C-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]-[C:6](=[O;D1;H0:7])-[OH;D1;+0:8]>>[CH3;D1;+0:1]-[O;H0;D2;+0:8]-[C:6](=[O;D1;H0:7])-[c:5]:[c:3](-[OH;D1;+0:2]):[c:4] | null | [] | null | null | 2 | HOUR | The 4-isopropyl-2-methoxymethoxybenzoic acid (5.3 g, 23.6 mmol) was dissolved in methylene chloride (75 mL) and MeOH (75 mL). Acetyl chloride (1 mL) was added to generate HCl. The reaction mixture was stirred for 2 h. The reaction was washed with water (2×150 mL), dried (MgSO4), and concentrated under vacuum. The crude... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Ether | Ester.Aromatic alcohol | null | null | c1ccccc1 | HO- | CCCCCC.C(Cl)Cl.CO | null | 2 | COCOc1cc(C(C)C)ccc1C(=O)O>CCCCCC.C(Cl)Cl.CO>COC(=O)c1ccc(C(C)C)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f3d29e400cd341f0b5639776912b6bd4 | CC(C)(C)OC(=O)N1CCCC(CO)C1.COC(=O)c1ccc(C(C)C)cc1O>>COC(=O)c1ccc(C(C)C)cc1OCC1CCCN(C(=O)OC(C)(C)C)C1 | OCC1CN(CCC1)C(=O)OC(C)(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(C)(C)C1=CC(=C(C(=O)OC)C=C1)O.N(=NC(=O)OC(C)C)C(=O)OC(C)C>>C(C)(C)(C)OC(=O)N1CC(CCC1)COC1=C(C(=O)OC)C=CC(=C1)C(C)C | O[CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[cH:12][c:13]1[OH:14]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH:9]([CH3:10])[CH3:11])[cH:12][c:13]1[O:14][CH2:15][CH:16]... | CC(C)(C)OC(=O)N1CCCC(CO)C1.COC(=O)c1ccc(C(C)C)cc1O | COC(=O)c1ccc(C(C)C)cc1OCC1CCCN(C(=O)OC(C)(C)C)C1 | null | null | C(Cl)Cl.C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccc(OCC2CCCNC2)cc1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4]-[#7:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[#7:5]-[C:4]-[C:2](-[CH2;D2;+0:1]-[O;H0;D2;+0:11]-[c:10](:[c:12]):[c:9]-[C:7](-[#8:6])=[O;D1;H0:8])-[C:3] | 43 | [{"value": 43.0, "product": "C(C)(C)(C)OC(=O)N1CC(CCC1)COC1=C(C(=O)OC)C=CC(=C1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.6, "product": "C(C)(C)(C)OC(=O)N1CC(CCC1)COC1=C(C(=O)OC)C=CC(=C1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | The methyl 4-isopropyl-2-hydroxybenzoate (4.4 g, 22.7 mmol) was dissolved in THF (100 mL). Then 3-(hydroxy-methyl)-1-tert-butoxycarbonylpiperidine (4.88 g, 22.7 mmol) and triphenylphosphine (7.14 g, 27.24 mmol) were added. The mixture was placed in an ice bath, and then diisopropyl azodicarboxylate (4.59 g, 22.7 mmol) ... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1.C1CC[NH]CC1 | HO- | C(Cl)Cl.C1CCOC1 | null | 16 | CC(C)(C)OC(=O)N1CCCC(CO)C1.COC(=O)c1ccc(C(C)C)cc1O>C(Cl)Cl.C1CCOC1>COC(=O)c1ccc(C(C)C)cc1OCC1CCCN(C(=O)OC(C)(C)C)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-64265ceffcb246c196f3dc6e771ef307 | COC(=O)c1ccc(C(C)C)cc1OCC1CCCN(C(=O)OC(C)(C)C)C1>>CC(C)c1ccc(C(=O)O)c(OCC2CCCN(C(=O)OC(C)(C)C)C2)c1 | C(C)(C)C1=CC(=C(C(=O)OC)C=C1)OCC1CN(CCC1)C(=O)OC(C)(C)C.O[Li].O>>C(C)(C)(C)OC(=O)N1CC(CCC1)COC1=C(C(=O)O)C=CC(=C1)C(C)C | C[O:10][C:8]([c:7]1[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:27][c:11]1[O:12][CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26]1)=[O:9]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[c:11]([O:12][CH2:13][CH:14]2[CH2:15][CH2:16][CH2:17... | COC(=O)c1ccc(C(C)C)cc1OCC1CCCN(C(=O)OC(C)(C)C)C1 | CC(C)c1ccc(C(=O)O)c(OCC2CCCN(C(=O)OC(C)(C)C)C2)c1 | null | null | O.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(OCC2CCCNC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 83.6 | [{"value": 83.6, "product": "C(C)(C)(C)OC(=O)N1CC(CCC1)COC1=C(C(=O)O)C=CC(=C1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 65 | CELSIUS | null | null | The methyl 4-isopropyl-2-(1-tert-butoxycarbonyl-piperidin-3-ylmethoxy)benzoate (1.53 g, 3.90 mmol) was dissolved in THF (15 mL). Then LiOH.H2O (0.36 g, 8.58 mmol) in water (5 mL) was added. The mixture was heated at 65° C. for 24 h. The reaction mixture was concentrated in vacuo and then redissolved in a mixture of EtO... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1CC[NH]CC1 | Other | O.C1CCOC1 | 65 | null | COC(=O)c1ccc(C(C)C)cc1OCC1CCCN(C(=O)OC(C)(C)C)C1>O.C1CCOC1>CC(C)c1ccc(C(=O)O)c(OCC2CCCN(C(=O)OC(C)(C)C)C2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-197def2531de41c1a5800dc10c81e8f3 | Nc1ccc(Cl)cn1.Nc1ncccc1C(=O)O.O=C(Cl)C(=O)Cl>>Cl.Nc1ncccc1C(=O)Nc1ccc(Cl)cn1 | N1=CC=CC=C1.C(C(=O)Cl)(=O)Cl.NC1=C(C(=O)O)C=CC=N1.NC1=NC=C(C=C1)Cl>>Cl.NC1=NC=CC=C1C(=O)NC1=NC=C(C=C1)Cl | [NH2:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][n:18]1.O[C:9]([c:8]1[c:3]([NH2:2])[n:4][cH:5][cH:6][cH:7]1)=[O:10].O=C(Cl)C(=O)[Cl:1]>>[ClH:1].[NH2:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[C:9](=[O:10])[NH:11][c:12]1[cH:13][cH:14][c:15]([Cl:16])[cH:17][n:18]1 | Nc1ccc(Cl)cn1.Nc1ncccc1C(=O)O.O=C(Cl)C(=O)Cl | Cl.Nc1ncccc1C(=O)Nc1ccc(Cl)cn1 | null | CN(C)C=O | ClCCl | Acylation | OtherReaction | 1594cf5835385d20ccf6bf195a66e3c2a67922d7fd1ff78b4b8bb896d3cd2627 | 5ced1cc9e0cb97cfb94bb570f8e59a8d9bacd5dab9880053be8261560108ed08 | O=C(Nc1ccccn1)c1cccnc1 | Cl-C(=O)-C(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6](-[N;D1;H2:7]):[#7;a:8]:[c:9].[NH2;D1;+0:10]-[c:11](:[c:12]):[#7;a:13]:[c:14]>>[ClH;D0;+0:1].[N;D1;H2:7]-[c:6](:[#7;a:8]:[c:9]):[c:4](-[C;H0;D3;+0:2](=[O;D1;H0:3])-[NH;D2;+0:10]-[c:11](:[c:12]):[#7;a:13]:[c:14]):[c:5] | 59.3 | [{"value": 59.3, "product": "Cl.NC1=NC=CC=C1C(=O)NC1=NC=C(C=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 60 | MINUTE | To a stirring suspension of 2-aminonicotinic acid (26.9 g, 194 mmol) in dichloromethane (120 mL) at 0° C., was added DMF (a few drops), followed by oxalyl chloride (20 mL, 194 mmol). The cold bath was removed, and the solution was allowed to stir for 60 min at room temperature. This solution was then transferred via ca... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccncc1.c1ccncc1 | HCl | CN(C)C=O.ClCCl | null | 1 | Nc1ccc(Cl)cn1.Nc1ncccc1C(=O)O.O=C(Cl)C(=O)Cl>CN(C)C=O.ClCCl>Cl.Nc1ncccc1C(=O)Nc1ccc(Cl)cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-56a1adc8b61e4717a5028e9720267380 | CC(C)(C)OC(=O)NCCCO.COC(=O)c1ccc(F)cc1O>>COC(=O)c1ccc(F)cc1OCCCNC(=O)OC(C)(C)C | FC1=CC(=C(C(=O)OC)C=C1)O.C(C)(C)(C)OC(=O)NCCCO>>C(C)(C)(C)OC(=O)NCCCOC1=C(C(=O)OC)C=CC(=C1)F | O[CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[OH:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([F:9])[cH:10][c:11]1[O:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[... | CC(C)(C)OC(=O)NCCCO.COC(=O)c1ccc(F)cc1O | COC(=O)c1ccc(F)cc1OCCCNC(=O)OC(C)(C)C | null | null | CCOCC | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[OH;D1;+0:9]):[c:10]>>[#8:4]-[C:5](=[O;D1;H0:6])-[c:7]:[c:8](-[O;H0;D2;+0:9]-[CH2;D2;+0:1]-[C:2]-[C:3]):[c:10] | null | [] | null | null | null | null | Using a procedure equivalent to Example 1-F, methyl 4-fluoro-2-hydroxybenzoate and 3-(tert-butoxycarbonylamino)-propanol gave the ether product as a white solid (20.6 g, 84%).
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1 | HO- | CCOCC | null | null | CC(C)(C)OC(=O)NCCCO.COC(=O)c1ccc(F)cc1O>CCOCC>COC(=O)c1ccc(F)cc1OCCCNC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4ebac061d5e49bf9ec62eaa9b650001 | C1COCCN1.COC(=O)c1ccc(F)cc1OCCCNC(=O)OC(C)(C)C>>COC(=O)c1ccc(N2CCOCC2)cc1OCCCNC(=O)OC(C)(C)C | C(C)(C)(C)OC(=O)NCCCOC1=C(C(=O)OC)C=CC(=C1)F.N1CCOCC1>>C(C)(C)(C)OC(=O)NCCCOC1=C(C(=O)OC)C=CC(=C1)N1CCOCC1 | [NH:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1.F[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:16]([O:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[cH:15][c:16]1[O:... | C1COCCN1.COC(=O)c1ccc(F)cc1OCCCNC(=O)OC(C)(C)C | COC(=O)c1ccc(N2CCOCC2)cc1OCCCNC(=O)OC(C)(C)C | null | null | null | Heteroatom Alkylation and Arylation | Buchwald-Hartwig/Ullmann-Goldberg/N-arylation secondary amine | a47b7d43ef99c1989f39629bd45f903079b03ac5a9d702fdbffdae93a63a79cd | b6b8e2cdb45054a35f5e8157d624f852c0601a09401556706e166b19536eb7a7 | c1ccc(N2CCOCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#8:6]1-[C:7]-[C:8]-[NH;D2;+0:9]-[C:10]-[C:11]-1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[N;H0;D3;+0:9]1-[C:8]-[C:7]-[#8:6]-[C:11]-[C:10]-1):[c:4]:[c:5] | 16 | [{"value": 16.0, "product": "C(C)(C)(C)OC(=O)NCCCOC1=C(C(=O)OC)C=CC(=C1)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | null | null | Using methods substantially equivalent to those described in Example 1-G, except that the reaction mixture was heated to 130° C., methyl 2-(3-tert-butoxycarbonylamino-propoxy)-4-(morpholin-4-yl)benzoate (2.39 g, 6.06 mmol, 16%) was prepared from methyl 2-(3-tert-butoxycarbonylamino-propoxy)-4-fluorobenzoate and morphol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary amine | Tertiary amine | C1COCCN1.c1ccccc1 | c1ccccc1.C1COCC[NH]1 | c1ccccc1.C1COCC[NH]1 | HF | null | 130 | null | C1COCCN1.COC(=O)c1ccc(F)cc1OCCCNC(=O)OC(C)(C)C>>COC(=O)c1ccc(N2CCOCC2)cc1OCCCNC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f5d7325b9cc94e09804b37d3859053e5 | COC(=O)c1ccc(N2CCOCC2)cc1OCCCNC(=O)OC(C)(C)C>>CC(C)(C)OC(=O)NCCCOc1cc(N2CCOCC2)ccc1C(=O)O | C(C)(C)(C)OC(=O)NCCCOC1=C(C(=O)OC)C=CC(=C1)N1CCOCC1.[OH-].[K+]>>C(C)(C)(C)OC(=O)NCCCOC1=C(C(=O)O)C=CC(=C1)N1CCOCC1 | C[O:27][C:25]([c:24]1[c:13]([O:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[cH:14][c:15]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[cH:22][cH:23]1)=[O:26]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][O:12][c:13]1[cH:14][c:15]([N:16]2[CH2:17][CH... | COC(=O)c1ccc(N2CCOCC2)cc1OCCCNC(=O)OC(C)(C)C | CC(C)(C)OC(=O)NCCCOc1cc(N2CCOCC2)ccc1C(=O)O | null | null | O.C(C)O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(N2CCOCC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 99.5 | [{"value": 99.0, "product": "C(C)(C)(C)OC(=O)NCCCOC1=C(C(=O)O)C=CC(=C1)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.5, "product": "C(C)(C)(C)OC(=O)NCCCOC1=C(C(=O)O)C=CC(=C1)N1CCOCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 2 | HOUR | The methyl 2-(3-tert-butoxycarbonylaminopropoxy)-4-(morpholin-4-yl)benzoate (2.34 g, 5.93 mmol) was diluted with ethanol (60 mL) and water (60 mL). Potassium hydroxide pellets (1.64 g, 29.2 mmol) were added, and the resulting mixture was heated to 70° C. After 2 h, the reaction mixture was concentrated in vacuo. The re... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.C1COCC[NH]1 | Other | O.C(C)O | 70 | 2 | COC(=O)c1ccc(N2CCOCC2)cc1OCCCNC(=O)OC(C)(C)C>O.C(C)O>CC(C)(C)OC(=O)NCCCOc1cc(N2CCOCC2)ccc1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2ed4140d900344f8850149539ced1594 | CC(C)(C)OC(=O)NCCO.CCOC(=O)c1ccc(F)cc1F>>CCOC(=O)c1ccc(F)cc1OCCNC(=O)OC(C)(C)C | FC1=C(C(=O)OCC)C=CC(=C1)F.C(C)(C)(C)OC(=O)NCCO.CC(C)([O-])C.[K+]>>C(C)(C)(C)OC(=O)NCCOC1=C(C(=O)OCC)C=CC(=C1)F | [OH:13][CH2:14][CH2:15][NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23].F[c:12]1[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:7][cH:8][c:9]([F:10])[cH:11]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][c:9]([F:10])[cH:11][c:12]1[O:13][CH2:14][CH2:15][NH:16][C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22]... | CC(C)(C)OC(=O)NCCO.CCOC(=O)c1ccc(F)cc1F | CCOC(=O)c1ccc(F)cc1OCCNC(=O)OC(C)(C)C | null | null | ClCCl.C1CCOC1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 4821d6d7238522ee9ef4538c00647e855becf4de3d9c939c0cec2b01c1e5e915 | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccccc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8]):[c:9].[C:10]-[C:11]-[OH;D1;+0:12]>>[C:10]-[C:11]-[O;H0;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8]):[c:9] | null | [] | 0 | CELSIUS | 20 | MINUTE | To a solution of 2-(tert-butoxycarbonylamino)ethanol (4.34 g, 26.9 mmol) in THF (16 mL) at 0° C. under N2, was added potassium tert-butoxide (K+−OtBu, 26.9 mL, 26.9 mmol, 1.0 M in THF). The reaction mixture was stirred for 20 min at 0° C. during which time a thick slurry formed. The anion solution was then poured into ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1 | HF | ClCCl.C1CCOC1 | 0 | 0.333333 | CC(C)(C)OC(=O)NCCO.CCOC(=O)c1ccc(F)cc1F>ClCCl.C1CCOC1>CCOC(=O)c1ccc(F)cc1OCCNC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a225ad6e575f4d5bb1d1fc9cc3450e55 | CC(C)(C)OC(=O)NCCOc1cc(N2CCOCC2)ccc1C(=O)O.Nc1cccnc1C(=O)Nc1ccc(Cl)cn1.O=C([O-])C(F)(F)F>>NCCOc1cc(N2CCOCC2)ccc1C(=O)Nc1cccnc1C(=O)Nc1ccc(Cl)cn1.O=C(O)C(F)(F)F | NC=1C(=NC=CC1)C(=O)NC1=NC=C(C=C1)Cl.C(C)(C)(C)OC(=O)NCCOC1=C(C(=O)O)C=CC(=C1)N1CCOCC1.FC(C(=O)[O-])(F)F>>FC(C(=O)O)(F)F.NCCOC1=C(C(=O)NC=2C(=NC=CC2)C(=O)NC2=NC=C(C=C2)Cl)C=CC(=C1)N1CCOCC1 | CC(C)(C)OC(=O)[NH:1][CH2:2][CH2:3][O:4][c:5]1[cH:6][c:7]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[cH:14][cH:15][c:16]1[C:17](O)=[O:18].[NH2:19][c:20]1[cH:21][cH:22][cH:23][n:24][c:25]1[C:26](=[O:27])[NH:28][c:29]1[cH:30][cH:31][c:32]([Cl:33])[cH:34][n:35]1.[O:36]=[C:37]([O-:38])[C:39]([F:40])([F:41])[F:42]>>[NH2:1... | CC(C)(C)OC(=O)NCCOc1cc(N2CCOCC2)ccc1C(=O)O.Nc1cccnc1C(=O)Nc1ccc(Cl)cn1.O=C([O-])C(F)(F)F | NCCOc1cc(N2CCOCC2)ccc1C(=O)Nc1cccnc1C(=O)Nc1ccc(Cl)cn1.O=C(O)C(F)(F)F | null | null | CN(C=O)C | Protection | OtherReaction | 2697e1cde97ce6b36a4bb65719f859b1cdcabdda76228456baf211310f680305 | 7be28c2b2dc32b89fb94d0f68f6267f37f885e2da768fcd4882818b94b2ee349 | O=C(Nc1cccnc1C(=O)Nc1ccccn1)c1ccc(N2CCOCC2)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3].O-[C;H0;D3;+0:4](=[O;D1;H0:5])-[c:6](:[c:7]):[c:8].[#7:9]-[C:10](=[O;D1;H0:11])-[c:12](:[#7;a:13]:[c:14]):[c:15](-[NH2;D1;+0:16]):[c:17].[F;D1;H0:18]-[C:19](-[F;D1;H0:20])(-[F;D1;H0:21])-[C:22](-[O-;H0;D1:23])=[O;D1;H0:24]>>[#7:9]-[C:10](=[O;D1;H0:11])-[c:12](:[#7;a:13]:[c:1... | 2 | [{"value": 2.0, "product": "FC(C(=O)O)(F)F.NCCOC1=C(C(=O)NC=2C(=NC=CC2)C(=O)NC2=NC=C(C=C2)Cl)C=CC(=C1)N1CCOCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using methods substantially equivalent to those described in Example 1-I, 3-amino-N-(5-chloropyridin-2-yl)-pyridine-2-carboxamide (321 mg, 1.29 mmol), N,N-dimethyl-formamide (0.2 mL) and 2-(2-tert-butoxycarbonylaminoethoxy)-4-(morpholin-4-yl)benzoic acid (500 mg, 1.36 mmol) yielded, after deprotection of the coupled pr... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Carboxylic acid.Ether.Primary amine.Boc | Carboxylic acid.Secondary amide.Primary amine | null | null | c1ccccc1.C1COCC[NH]1.c1ccncc1.c1ccncc1 | HO- | CN(C=O)C | null | null | CC(C)(C)OC(=O)NCCOc1cc(N2CCOCC2)ccc1C(=O)O.Nc1cccnc1C(=O)Nc1ccc(Cl)cn1.O=C([O-])C(F)(F)F>CN(C=O)C>NCCOc1cc(N2CCOCC2)ccc1C(=O)Nc1cccnc1C(=O)Nc1ccc(Cl)cn1.O=C(O)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-484c18b173124ccca2ff61658cea3a7d | COC(=O)c1ccncc1NC(=O)c1ccc(N2CCCC2)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>>CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)Nc2cnccc2C(=O)O)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC=2C=NC=CC2C(=O)OC)C=CC(=C1)N1CCCC1.[OH-].[Na+]>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC=2C=NC=CC2C(=O)O)C=CC(=C1)N1CCCC1 | C[O:35][C:33]([c:32]1[c:27]([NH:26][C:24]([c:23]2[c:13]([O:12][CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:37][CH2:36]3)[cH:14][c:15]([N:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)[cH:21][cH:22]2)=[O:25])[cH:28][n:29][cH:30][cH:31]1)=[O:34]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:... | COC(=O)c1ccncc1NC(=O)c1ccc(N2CCCC2)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)Nc2cnccc2C(=O)O)CC1 | null | null | CO.C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1cccnc1)c1ccc(N2CCCC2)cc1OC1CCNCC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | 4 | HOUR | A solution of methyl 3-[2-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoylamino]pyridine-4-carboxylate (2.78 g, 5.3 mmol) in MeOH (100 mL) and THF (50 mL) was treated with 1 N NaOH (11 mL) and stirred at ambient temperature for 4 h. The reaction was quenched with glacial acetic acid (1 g) and concen... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]CC1.c1ccccc1.C1CC[NH]C1.c1ccncc1 | Other | CO.C1CCOC1 | null | 4 | COC(=O)c1ccncc1NC(=O)c1ccc(N2CCCC2)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>CO.C1CCOC1>CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)Nc2cnccc2C(=O)O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5575b543a6ca43cabe4e4beafdc4cd23 | CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2-c2nc3cnccc3c(=O)o2)CC1.Nc1ccc(Cl)cn1>>CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)Nc2cnccc2C(=O)Nc2ccc(Cl)cn2)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C=CC(=C1)N1CCCC1)C=1OC(C2=C(N1)C=NC=C2)=O.C(C)OCC.C(C=C)[Mg]Br.NC1=NC=C(C=C1)Cl>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC=2C=NC=CC2C(=O)NC2=NC=C(C=C2)Cl)C=CC(=C1)N1CCCC1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][c:15]([N:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)[cH:21][cH:22][c:23]2-[c:24]2[o:25][c:33](=[O:34])[c:32]3[c:27]([n:26]2)[cH:28][n:29][cH:30][cH:31]3)[CH2:43][CH2:44]1.[NH2:35][c:36]1[cH:37][cH:38][c:39]([Cl:40])[cH:41][n:42... | CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2-c2nc3cnccc3c(=O)o2)CC1.Nc1ccc(Cl)cn1 | CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)Nc2cnccc2C(=O)Nc2ccc(Cl)cn2)CC1 | null | null | C1CCOC1 | Acylation | OtherReaction | b47b3587e7ae57e8006790ee803a5e0f02b71ebe0cd3e0556d0df0fb445694e1 | 4accd3f274dad8ca7d44350b7d7da15181b5e5579c068528178b23416d2aea4a | O=C(Nc1ccccn1)c1ccncc1NC(=O)c1ccc(N2CCCC2)cc1OC1CCNCC1 | [#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[c:7]2:[c:8]:[#7;a:9]:[c:10]:[c:11]:[c:12]:2:[c;H0;D3;+0:13](=[O;D1;H0:14]):[o;H0;D2;+0:15]:1):[c:16]:[c:17].[NH2;D1;+0:18]-[c:19](:[c:20]):[#7;a:21]:[c:22]>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[C;H0;D3;+0:5](=[O;H0;D1;+0:15])-[NH;D2;+0:6]-[c:7]1:[c:8... | 100 | [{"value": 99.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC=2C=NC=CC2C(=O)NC2=NC=C(C=C2)Cl)C=CC(=C1)N1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 100.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC=2C=NC=CC2C(=O)NC2=NC=C(C=C2)Cl)C=CC(=C1)N1CCCC1", "details": "CALCULATEDPERCENTYIEL... | null | null | 5 | MINUTE | A solution of 2-amino-5-chloropyridine (52 mg, 0.4 mmol) in THF (10 mL) was cooled to 0° C. and treated with a 1 M diethyl ether solution of allylmagnesium bromide (0.4 mL). The mixture was stirred for 5 minutes before adding 2-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)phenyl]-4H-pyrido[3,4-d][1,3]... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide.Secondary amide | c1nc2cnccc2co1 | c1ccncc1 | C1CC[NH]CC1.c1ccccc1.C1CC[NH]C1.c1ccncc1.c1ccncc1 | null | C1CCOC1 | null | 0.083333 | CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2-c2nc3cnccc3c(=O)o2)CC1.Nc1ccc(Cl)cn1>C1CCOC1>CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)Nc2cnccc2C(=O)Nc2ccc(Cl)cn2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ccc603e9536e469d9837ac6520ce0c29 | CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)Nc2cnccc2C(=O)Nc2ccc(Cl)cn2)CC1>>O=C(Nc1ccc(Cl)cn1)c1ccncc1NC(=O)c1ccc(N2CCCC2)cc1OC1CCNCC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC=2C=NC=CC2C(=O)NC2=NC=C(C=C2)Cl)C=CC(=C1)N1CCCC1.FC(C(=O)O)(F)F>>FC(C(=O)O)(F)F.ClC=1C=CC(=NC1)NC(=O)C1=C(C=NC=C1)NC(C1=C(C=C(C=C1)N1CCCC1)OC1CCNCC1)=O | CC(C)(C)OC(=O)[N:35]1[CH2:34][CH2:33][CH:32]([O:31][c:30]2[c:20]([C:18]([NH:17][c:16]3[c:11]([C:2](=[O:1])[NH:3][c:4]4[cH:5][cH:6][c:7]([Cl:8])[cH:9][n:10]4)[cH:12][cH:13][n:14][cH:15]3)=[O:19])[cH:21][cH:22][c:23]([N:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)[cH:29]2)[CH2:37][CH2:36]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6]... | CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)Nc2cnccc2C(=O)Nc2ccc(Cl)cn2)CC1 | O=C(Nc1ccc(Cl)cn1)c1ccncc1NC(=O)c1ccc(N2CCCC2)cc1OC1CCNCC1 | null | null | C1(=CC=CC=C1)OC.C(Cl)Cl | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(Nc1ccccn1)c1ccncc1NC(=O)c1ccc(N2CCCC2)cc1OC1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 89 | [{"value": 89.0, "product": "FC(C(=O)O)(F)F.ClC=1C=CC(=NC1)NC(=O)C1=C(C=NC=C1)NC(C1=C(C=C(C=C1)N1CCCC1)OC1CCNCC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The 3-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoylamino]-N-(5-chloropyridin-2-yl)-pyridine-4-carboxamide (109 mg, 0.18 mmol) was dissolved in CH2Cl2 (2 mL) with anisole (1 mL). The solution was treated with trifluoroacetic acid (1 mL) at room temperature for 2 h. The mixture was concentrated t... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccncc1.c1ccncc1.c1ccccc1.C1CC[NH]C1.C1CCNCC1 | HO- | C1(=CC=CC=C1)OC.C(Cl)Cl | null | null | CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)Nc2cnccc2C(=O)Nc2ccc(Cl)cn2)CC1>C1(=CC=CC=C1)OC.C(Cl)Cl>O=C(Nc1ccc(Cl)cn1)c1ccncc1NC(=O)c1ccc(N2CCCC2)cc1OC1CCNCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-871b6393702f46e4bccf3ff3709423c2 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2-c2nc3cnccc3c(=O)o2)CC1.Nc1ccc(Cl)cn1>>CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2cnccc2C(=O)Nc2ccc(Cl)cn2)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C=CC(=C1)C(C)(C)C)C=1OC(C2=C(N1)C=NC=C2)=O.[C-]#N.[K+].ClC=1C=CC(=NC1)N>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC=2C=NC=CC2C(=O)NC2=NC=C(C=C2)Cl)C=CC(=C1)C(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21][c:22]2-[c:23]2[o:24][c:32](=[O:33])[c:31]3[c:26]([n:25]2)[cH:27][n:28][cH:29][cH:30]3)[CH2:42][CH2:43]1.[NH2:34][c:35]1[cH:36][cH:37][c:38]([Cl:39])[cH:40][n:41]1>>[C... | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2-c2nc3cnccc3c(=O)o2)CC1.Nc1ccc(Cl)cn1 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2cnccc2C(=O)Nc2ccc(Cl)cn2)CC1 | null | null | CN(C)C=O | Acylation | OtherReaction | b47b3587e7ae57e8006790ee803a5e0f02b71ebe0cd3e0556d0df0fb445694e1 | 4accd3f274dad8ca7d44350b7d7da15181b5e5579c068528178b23416d2aea4a | O=C(Nc1ccccn1)c1ccncc1NC(=O)c1ccccc1OC1CCNCC1 | [#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[c:7]2:[c:8]:[#7;a:9]:[c:10]:[c:11]:[c:12]:2:[c;H0;D3;+0:13](=[O;D1;H0:14]):[o;H0;D2;+0:15]:1):[c:16]:[c:17].[NH2;D1;+0:18]-[c:19](:[c:20]):[#7;a:21]:[c:22]>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[C;H0;D3;+0:5](=[O;H0;D1;+0:15])-[NH;D2;+0:6]-[c:7]1:[c:8... | 23.5 | [{"value": 23.5, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC=2C=NC=CC2C(=O)NC2=NC=C(C=C2)Cl)C=CC(=C1)C(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | null | null | A mixture of 2-[2-(1-tert-butoxycarbonylpiperidin-4-yl-oxy)-4-tert-butylphenyl]-4H-pyrido[3,4-d][1,3]oxazin-4-one (100 mg, 0.21 mmol), KCN (100 mg), 5-chloro-2-aminopyridine (53 mg, 0.42 mmol), and dry DMF (2 mL) was heated at 70° C. for 4 h, then quenched with brine (25 mL). The mixture was extracted with 10% MQOH in ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide.Secondary amide | c1nc2cnccc2co1 | c1ccncc1 | C1CC[NH]CC1.c1ccccc1.c1ccncc1.c1ccncc1 | null | CN(C)C=O | 70 | null | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2-c2nc3cnccc3c(=O)o2)CC1.Nc1ccc(Cl)cn1>CN(C)C=O>CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2cnccc2C(=O)Nc2ccc(Cl)cn2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b8dcbc4583734b79ac012a5a7b4eaf05 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2cnccc2C(=O)Nc2ccc(Cl)cn2)CC1>>CC(C)(C)c1ccc(C(=O)Nc2cnccc2C(=O)Nc2ccc(Cl)cn2)c(OC2CCNCC2)c1 | C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC=2C=NC=CC2C(=O)NC2=NC=C(C=C2)Cl)C=CC(=C1)C(C)(C)C.C1(=CC=CC=C1)OC.FC(C(=O)O)(F)F>>C(C)(C)(C)C1=CC(=C(C(=O)NC=2C=NC=CC2C(=O)NC2=NC=C(C=C2)Cl)C=C1)OC1CCNCC1 | CC(C)(C)OC(=O)[N:33]1[CH2:32][CH2:31][CH:30]([O:29][c:28]2[c:8]([C:9](=[O:10])[NH:11][c:12]3[cH:13][n:14][cH:15][cH:16][c:17]3[C:18](=[O:19])[NH:20][c:21]3[cH:22][cH:23][c:24]([Cl:25])[cH:26][n:27]3)[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:36]2)[CH2:35][CH2:34]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c... | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2cnccc2C(=O)Nc2ccc(Cl)cn2)CC1 | CC(C)(C)c1ccc(C(=O)Nc2cnccc2C(=O)Nc2ccc(Cl)cn2)c(OC2CCNCC2)c1 | null | null | C(Cl)Cl | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(Nc1ccccn1)c1ccncc1NC(=O)c1ccccc1OC1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 63 | [{"value": 63.0, "product": "C(C)(C)(C)C1=CC(=C(C(=O)NC=2C=NC=CC2C(=O)NC2=NC=C(C=C2)Cl)C=C1)OC1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | The 3-[2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(tert-butyl)benzoylamino]-N-(5-chloropyridin-2-yl)pyridine-4-carboxamide (60 mg, 0.1 mmol) was mixed with anisole (1 mL) and CH2Cl2 (2 mL) then treated with trifluoroacetic acid (1 mL). The reaction was stirred at ambient temperature for 4 h, concentrated under vacuum... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.c1ccncc1.c1ccncc1.C1CCNCC1 | HO- | C(Cl)Cl | null | 4 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2cnccc2C(=O)Nc2ccc(Cl)cn2)CC1>C(Cl)Cl>CC(C)(C)c1ccc(C(=O)Nc2cnccc2C(=O)Nc2ccc(Cl)cn2)c(OC2CCNCC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ab34c9d7e1bb44e1bf823119269e3b8a | CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)O)CC1.COC(=O)c1sccc1N>>COC(=O)c1sccc1NC(=O)c1ccc(N2CCCC2)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | C(C)(C)(C)ON1C(CC(CC1)OC1=C(C(=O)NC2=C(SC=C2)C(=O)OC)C=CC(=C1)N1CCCC1)=C=O.C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)O)C=CC(=C1)N1CCCC1.NC1=C(SC=C1)C(=O)OC>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC2=C(SC=C2)C(=O)OC)C=CC(=C1)N1CCCC1 | O[C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([N:17]2[CH2:18][CH2:19][CH2:20][CH2:21]2)[cH:22][c:23]1[O:24][CH:25]1[CH2:26][CH2:27][N:28]([C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[CH2:36][CH2:37]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][cH:7][cH:8][c:9]1[NH2:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[s:6][cH:7][cH:... | CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)O)CC1.COC(=O)c1sccc1N | COC(=O)c1sccc1NC(=O)c1ccc(N2CCCC2)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccsc1)c1ccc(N2CCCC2)cc1OC1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1-[NH2;D1;+0:14]>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[#16;a:10]:[c:11]:[c:12]:[c:13]:1-[NH;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 58 | [{"value": 58.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC2=C(SC=C2)C(=O)OC)C=CC(=C1)N1CCCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using methods substantially equivalent to those described in Example 12-C, methyl 3-[2-(1-tert-butoxy-carbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoylamino]-thiophene-2-carboxylate was prepared in a 58% yield from 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoic acid and methyl 3-aminothiophen... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccsc1.c1ccccc1.C1CC[NH]C1.C1CC[NH]CC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)O)CC1.COC(=O)c1sccc1N>>COC(=O)c1sccc1NC(=O)c1ccc(N2CCCC2)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e4eb1700d8884e7e92062637cba3ef88 | COC(=O)c1sccc1NC(=O)c1ccc(N2CCCC2)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>>CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)Nc2ccsc2C(=O)O)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC2=C(SC=C2)C(=O)OC)C=CC(=C1)N1CCCC1.CCO.[OH-].[K+]>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC2=C(SC=C2)C(=O)O)C=CC(=C1)N1CCCC1 | C[O:34][C:32]([c:31]1[c:27]([NH:26][C:24]([c:23]2[c:13]([O:12][CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:36][CH2:35]3)[cH:14][c:15]([N:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)[cH:21][cH:22]2)=[O:25])[cH:28][cH:29][s:30]1)=[O:33]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8... | COC(=O)c1sccc1NC(=O)c1ccc(N2CCCC2)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)Nc2ccsc2C(=O)O)CC1 | null | null | O | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1ccsc1)c1ccc(N2CCCC2)cc1OC1CCNCC1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[#16;a:5]>>[#16;a:5]:[c:4]-[C:2](=[O;D1;H0:3])-[OH;D1;+0:1] | 94.4 | [{"value": 94.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC2=C(SC=C2)C(=O)O)C=CC(=C1)N1CCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.4, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC2=C(SC=C2)C(=O)O)C=CC(=C1)N1CCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the methyl 3-[2-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-4-(pyrrolidin-1-yl)benzoylamino]-thiophene-2-carboxylate (3.8 g, 7.2 mmol) and EtOH (100 mL) was treated with a solution of KOH (0.88 g) in water (80 mL). The reaction mixture was refluxed overnight, quenched with glacial acetic acid (1.5 mL) and c... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]CC1.c1ccccc1.C1CC[NH]C1.c1ccsc1 | Other | O | null | null | COC(=O)c1sccc1NC(=O)c1ccc(N2CCCC2)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>O>CC(C)(C)OC(=O)N1CCC(Oc2cc(N3CCCC3)ccc2C(=O)Nc2ccsc2C(=O)O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d3a29ac2466649be9f7409d0a2015af4 | CN(C)C=O.COC(=O)c1ccc(F)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>>COC(=O)c1ccc(N(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | CN(C)C=O.C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)F.N1CCOCC1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)N(C)C | O=C[N:9]([CH3:10])[CH3:11].F[c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:13]([O:14][CH:15]2[CH2:16][CH2:17][N:18]([C:19](=[O:20])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:26][CH2:27]2)[cH:12]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([N:9]([CH3:10])[CH3:11])[cH:12][c:13]1[O:14][CH:15]1[CH2:16][CH2:... | CN(C)C=O.COC(=O)c1ccc(F)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | COC(=O)c1ccc(N(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | [Cl-].[Na+].O | Heteroatom Alkylation and Arylation | OtherReaction | 79e5fcace80b85c39b8b97f2b6fb84586538378f01cb44375f57f3ff58a947fa | da441520990db3b7dfc8421b343d1a69dceb643d35ca5c86f0c23a5d017d38e3 | c1ccc(OC2CCNCC2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].O=C-[N;H0;D3;+0:6](-[C;D1;H3:7])-[C;D1;H3:8]>>[C;D1;H3:7]-[N;H0;D3;+0:6](-[C;D1;H3:8])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | 59 | [{"value": 59.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)N(C)C", "details": "PERCENTYIELD", "is_desired": false}] | 110 | CELSIUS | null | null | The 4-dimethylamino compound was obtained in the following preparation in which the dimethylamino group was derived from in situ decomposition of the solvent DMF: A mixture of methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-fluorobenzoate (6.45 g, 18.25 mmol), morpholine (8 g, 91.26 mmol), Cs2CO3 (11.8 g, 36.5 mmol... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amide | Tertiary amine | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CC[NH]CC1 | HF | [Cl-].[Na+].O | 110 | null | CN(C)C=O.COC(=O)c1ccc(F)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>[Cl-].[Na+].O>COC(=O)c1ccc(N(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ca0abe26feb74a2bbda23271876d02b4 | CN(C)c1ccc(C(=O)O)c(OC2CCN(C(=O)OC(C)(C)C)CC2)c1.COC(=O)c1cscc1N>>COC(=O)c1cscc1NC(=O)c1ccc(N(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | C(C)(C)(C)ON1C(CC(CC1)OC1=C(C(=O)NC=2C(=CSC2)C(=O)OC)C=CC(=C1)N(C)C)=C=O.C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)O)C=CC(=C1)N(C)C.NC=1C(=CSC1)C(=O)OC>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC=2C(=CSC2)C(=O)OC)C=CC(=C1)N(C)C | O[C:11](=[O:12])[c:13]1[cH:14][cH:15][c:16]([N:17]([CH3:18])[CH3:19])[cH:20][c:21]1[O:22][CH: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.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][s:7][cH:8][c:9]1[NH2:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][s:7][cH:8][c:9]1[NH:10][... | CN(C)c1ccc(C(=O)O)c(OC2CCN(C(=O)OC(C)(C)C)CC2)c1.COC(=O)c1cscc1N | COC(=O)c1cscc1NC(=O)c1ccc(N(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Nc1ccsc1)c1ccccc1OC1CCNCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[#16;a:11]:[c:12]:[c:13]:1-[NH2;D1;+0:14]>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]1:[c:10]:[#16;a:11]:[c:12]:[c:13]:1-[NH;D2;+0:14]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 51 | [{"value": 51.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC=2C(=CSC2)C(=O)OC)C=CC(=C1)N(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using methods substantially equivalent to those described in Example 12-C, methyl 4-[2-(1-tert-butoxy-carbonylpiperidin-4-yloxy)-4-(dimethylamino)benzoylamino]-thiophene-3-carboxylate was prepared in a 51% yield from 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(dimethyl-amino)benzoic acid and methyl 4-aminothiophene-3... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccsc1.c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | CN(C)c1ccc(C(=O)O)c(OC2CCN(C(=O)OC(C)(C)C)CC2)c1.COC(=O)c1cscc1N>>COC(=O)c1cscc1NC(=O)c1ccc(N(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1c025f3a95bc4e6b86e1a8dfda099309 | COC(=O)c1cscc1NC(=O)c1ccc(N(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>>CN(C)c1ccc(-c2nc3cscc3c(=O)o2)c(OC2CCN(C(=O)OC(C)(C)C)CC2)c1 | C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)NC=2C(=CSC2)C(=O)OC)C=CC(=C1)N(C)C.[OH-].[Na+]>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C=CC(=C1)N(C)C)C=1OC(C=2C(N1)=CSC2)=O | CO[C:15]([c:14]1[c:10]([NH:9][C:8]([c:7]2[cH:6][cH:5][c:4]([N:2]([CH3:1])[CH3:3])[cH:33][c:18]2[O:19][CH:20]2[CH2:21][CH2:22][N:23]([C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH2:31][CH2:32]2)=[O:17])[cH:11][s:12][cH:13]1)=[O:16]>>[CH3:1][N:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[n:9][c:10]3[cH:11][s:1... | COC(=O)c1cscc1NC(=O)c1ccc(N(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | CN(C)c1ccc(-c2nc3cscc3c(=O)o2)c(OC2CCN(C(=O)OC(C)(C)C)CC2)c1 | null | null | CO.C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | f165d441235a395ef6db5f790e934e063854e912f9b5233524dc0f2cf0d523a0 | 2fd2cda60f919882649147d24290e6fb253175d1342fb909035293b0bba9a63a | O=c1oc(-c2ccccc2OC2CCNCC2)nc2cscc12 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#16;a:5]:[c:6]:[c:7]:1-[NH;D2;+0:8]-[C;H0;D3;+0:9](=[O;H0;D1;+0:10])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](-[#8:15]):[c:16]>>[#8:15]-[c:14](:[c:16]):[c;H0;D3;+0:11](-[c;H0;D3;+0:9]1:[n;H0;D2;+0:8]:[c:7]2:[c:6]:[#16;a:5]:[c:4]:[c:3]:2:[c;H0;D3;+0:1](=[O;D1;H0:2]):[o;H0;D2;... | 92.2 | [{"value": 92.2, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C=CC(=C1)N(C)C)C=1OC(C=2C(N1)=CSC2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | A solution of methyl 4-[2-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-4-(dimethylamino)benzoylamino]thiophene-3-carboxylate (2.3 g, 4.6 mmol) in MeOH (100 mL) and THF (50 mL) was treated with a solution of 1 N aqueous NaOH (10 mL) at 60° C. for 24 h. The mixture was concentrated to dryness, mixed with brine (25 mL) and g... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Secondary amide | null | c1ccsc1 | c1nc2cscc2co1 | c1ccccc1.c1nc2cscc2co1.C1CC[NH]CC1 | HO- | CO.C1CCOC1 | 0 | 8 | COC(=O)c1cscc1NC(=O)c1ccc(N(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>CO.C1CCOC1>CN(C)c1ccc(-c2nc3cscc3c(=O)o2)c(OC2CCN(C(=O)OC(C)(C)C)CC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-6dec4c08d411456ebba835a408a5e987 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)O)CC1>>CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2CO)CC1 | [B-][N+](C)(C)C.C(C)(C)(C)C1=CC(=C(C(=O)O)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C.[B-][N+](C)(C)C>>C(C)(C)(C)C1=CC(=C(CO)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C | O=[C:23]([c:22]1[c:13]([O:12][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:26][CH2:25]2)[cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]1)[OH:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][c:15]([C:16]([CH3:17])(... | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)O)CC1 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2CO)CC1 | null | null | O1CCCC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc(OC2CCNCC2)cc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 4 | HOUR | The alcohol may be prepared as follows: To a solution of borane-trimethylamine complex (1.35 mL of a 1 M solution in tetrahydrofuran) in tetrahydrofuran (3 mL) stirring at 0° C., a solution of 4-tert-butyl-2-(1-Boc-piperidine-4-yl-oxy)benzoic acid (0.51 g, 1.35 mmol) in tetrahydrofuran (7 mL) was added slowly via cannu... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | C1CC[NH]CC1.c1ccccc1 | Other | O1CCCC1 | null | 4 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)O)CC1>O1CCCC1>CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2CO)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-00a42f08ec8c43148c1375dbb7365c1d | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2CN2C(=O)c3ccccc3C2=O)CC1>>CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2CN)CC1 | C(C)(C)(C)C1=CC(=C(CN2C(C=3C(C2=O)=CC=CC3)=O)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C.NN>>C(C)(C)(C)C1=CC(=C(CN)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C | O=C1c2ccccc2C(=O)[N:24]1[CH2:23][c:22]1[c:13]([O:12][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:26][CH2:25]2)[cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][c:15]([C... | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2CN2C(=O)c3ccccc3C2=O)CC1 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2CN)CC1 | null | null | C(Cl)Cl.C(C)O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | c1ccc(OC2CCNCC2)cc1 | O=C1-[N;H0;D3;+0:1](-[C:2]-[c:3])-C(=O)-c2:c:c:c:c:c:2-1>>[NH2;D1;+0:1]-[C:2]-[c:3] | 95.7 | [{"value": 95.0, "product": "C(C)(C)(C)C1=CC(=C(CN)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.7, "product": "C(C)(C)(C)C1=CC(=C(CN)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of N-[4-tert-butyl-2-(1-Boc-piperidin-4-yloxy)benzyl]phthalimide (0.243 g, 0.49 mmol) in 3 mL absolute ethanol was added hydrazine (0.062 mL, 1.98 mmol) at room temperature. The reaction mixture was stirred at room temperature for 2 h, diluted with methylene chloride; and the resulting white solid filtere... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | C1CC[NH]CC1.c1ccccc1 | HO- | C(Cl)Cl.C(C)O | null | 2 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2CN2C(=O)c3ccccc3C2=O)CC1>C(Cl)Cl.C(C)O>CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2CN)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ee29ab3c79d147be90897a0680970a2d | Nc1ccc(Cl)cc1.O=C(Cl)c1cccnc1>>O=C(Nc1ccc(Cl)cc1)c1cccnc1Cl | C(C1=CN=CC=C1)(=O)Cl.ClC1=CC=C(N)C=C1.C(C)N(CC)CC.ClCCCl>>ClC1=CC=C(C=C1)NC(C1=C(N=CC=C1)Cl)=O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1.[O:1]=[C:2]([c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1)[Cl:17]>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[cH:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][n:15][c:16]1[Cl:17] | Nc1ccc(Cl)cc1.O=C(Cl)c1cccnc1 | O=C(Nc1ccc(Cl)cc1)c1cccnc1Cl | null | null | null | Acylation | OtherReaction | b8b801d661aa1b765ccba3a9581618fcedc62dc62d7673fcb9123336188f178d | 66a2d985d0feddf4cfbcfcda0552b4c93401dee4e39ffbe91f30ac58e186e158 | O=C(Nc1ccccc1)c1cccnc1 | [Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[cH;D2;+0:6]:[#7;a:7]:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[Cl;H0;D1;+0:1]-[c;H0;D3;+0:6](:[#7;a:7]:[c:8]):[c:4](-[C;H0;D3;+0:2](=[O;D1;H0:3])-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]):[c:5] | 100 | [{"value": 100.0, "product": "ClC1=CC=C(C=C1)NC(C1=C(N=CC=C1)Cl)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of nicotinoyl chloride (0.500 g, 2.84 mmol) in 15 mL of 1,2-dichloroethane was added 4-chloroaniline (0.432 g, 3.41 mmol) and triethylamine (0.400 mL, 2.84 mmol), respectively. The reaction mixture was stirred at room temperature for 1 h before it was washed with water (2×), brine (1×), dried over Na2SO4,... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Primary amine | Aromatic halide.Secondary amide | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | null | null | null | 1 | Nc1ccc(Cl)cc1.O=C(Cl)c1cccnc1>>O=C(Nc1ccc(Cl)cc1)c1cccnc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-dff22854df074758802314edeec71394 | COCOc1cc(C(C)C)ccc1C(=O)O>>COCOc1cc(C(C)C)ccc1CO | C(C)(C)C1=CC(=C(C(=O)O)C=C1)OCOC.CN1CCOCC1.[BH4-].[Na+].ClC(=O)OCC.C(=O)=O>>C(C)(C)C1=CC(=C(CO)C=C1)OCOC | O=[C:14]([c:13]1[c:5]([O:4][CH2:3][O:2][CH3:1])[cH:6][c:7]([CH:8]([CH3:9])[CH3:10])[cH:11][cH:12]1)[OH:15]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][c:7]([CH:8]([CH3:9])[CH3:10])[cH:11][cH:12][c:13]1[CH2:14][OH:15] | COCOc1cc(C(C)C)ccc1C(=O)O | COCOc1cc(C(C)C)ccc1CO | null | null | O1CCCC1.CO | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccccc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3](:[c:4]):[c:5]>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 50 | [{"value": 50.0, "product": "C(C)(C)C1=CC(=C(CO)C=C1)OCOC", "details": "PERCENTYIELD", "is_desired": false}] | -10 | CELSIUS | 20 | MINUTE | To a solution of 4-isopropyl-2-(methoxymethoxy)benzoic acid, which may be prepared as described in Exmple 6-B, (2.40 g, 11.0 mmol) and 4-methylmorpholine (1.18 mL, 11.0 mmol) in 50 mL dry tetrahydrofuran at −10° C. was added dropwise ethyl chloroformate (1.02 mL, 11.0 mmol). After stirring at −10° C. for 20 min, sodium... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1ccccc1 | Other | O1CCCC1.CO | -10 | 0.333333 | COCOc1cc(C(C)C)ccc1C(=O)O>O1CCCC1.CO>COCOc1cc(C(C)C)ccc1CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7c19fc9f6df5401bb5c66e1c1807f9a4 | CC(C)(C)OC(=O)NCCO.CC(C)c1ccc(CNc2ncccc2C(=O)Nc2ccc(Cl)cc2)c(O)c1>>CC(C)c1ccc(CNc2ncccc2C(=O)Nc2ccc(Cl)cc2)c(OCCNC(=O)OC(C)(C)C)c1 | ClC1=CC=C(C=C1)NC(=O)C=1C(=NC=CC1)NCC1=C(C=C(C=C1)C(C)C)O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C(=O)(OC(C)(C)C)NCCO.N(=NC(=O)OCC)C(=O)OCC>>C(=O)(OC(C)(C)C)NCCOC1=C(CNC2=NC=CC=C2C(=O)NC2=CC=C(C=C2)Cl)C=CC(=C1)C(C)C | [OH:27][CH2:28][CH2:29][NH:30][C:31](=[O:32])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37].O[c:26]1[c:7]([CH2:8][NH:9][c:10]2[n:11][cH:12][cH:13][cH:14][c:15]2[C:16](=[O:17])[NH:18][c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]2)[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:38]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][... | CC(C)(C)OC(=O)NCCO.CC(C)c1ccc(CNc2ncccc2C(=O)Nc2ccc(Cl)cc2)c(O)c1 | CC(C)c1ccc(CNc2ncccc2C(=O)Nc2ccc(Cl)cc2)c(OCCNC(=O)OC(C)(C)C)c1 | null | null | O1CCCC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 8915084acbaaf997bf0f89ff5187cb2f89c25dc683fffc57b3391298c8430dd9 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | O=C(Nc1ccccc1)c1cccnc1NCc1ccccc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6].[C:7]-[C:8]-[OH;D1;+0:9]>>[C:7]-[C:8]-[O;H0;D2;+0:9]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]):[c:6] | 33.7 | [{"value": 30.0, "product": "C(=O)(OC(C)(C)C)NCCOC1=C(CNC2=NC=CC=C2C(=O)NC2=CC=C(C=C2)Cl)C=CC(=C1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 33.7, "product": "C(=O)(OC(C)(C)C)NCCOC1=C(CNC2=NC=CC=C2C(=O)NC2=CC=C(C=C2)Cl)C=CC(=C1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | DAY | To a solution of N-(4-chlorophenyl)-2-[2-hydroxy-4-isopropylbenzylamino]pyridine-3-carboxamide (0.050 g, 0.13 mmol), triphenylphosphine (0.033 g, 0.13 mmol) and N-Boc-ethanolamine (0.018 mg, 0.11 mmol) in 0.3 mL tetrahydrofuran at −10° C. was added a solution of diethyl azodicarboxylate (0.02 mL, 0.13 mmol) in 0.3 mL t... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1.c1ccccc1 | HO- | O1CCCC1 | null | 72 | CC(C)(C)OC(=O)NCCO.CC(C)c1ccc(CNc2ncccc2C(=O)Nc2ccc(Cl)cc2)c(O)c1>O1CCCC1>CC(C)c1ccc(CNc2ncccc2C(=O)Nc2ccc(Cl)cc2)c(OCCNC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ef4ebcbafe59483fa610a6277a58bc51 | CC(C)c1ccc(CNc2ncccc2C(=O)Nc2ccc(Cl)cc2)c(OCCNC(=O)OC(C)(C)C)c1>>CC(C)c1ccc(CNc2ncccc2C(=O)Nc2ccc(Cl)cc2)c(OCCN)c1 | C(=O)(OC(C)(C)C)NCCOC1=C(CNC2=NC=CC=C2C(=O)NC2=CC=C(C=C2)Cl)C=CC(=C1)C(C)C.C(Cl)Cl>>NCCOC1=C(CNC2=NC=CC=C2C(=O)NC2=CC=C(C=C2)Cl)C=CC(=C1)C(C)C | CC(C)(C)OC(=O)[NH:30][CH2:29][CH2:28][O:27][c:26]1[c:7]([CH2:8][NH:9][c:10]2[n:11][cH:12][cH:13][cH:14][c:15]2[C:16](=[O:17])[NH:18][c:19]2[cH:20][cH:21][c:22]([Cl:23])[cH:24][cH:25]2)[cH:6][cH:5][c:4]([CH:2]([CH3:1])[CH3:3])[cH:31]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][c:7]([CH2:8][NH:9][c:10]2[n:11][cH:12][cH:13... | CC(C)c1ccc(CNc2ncccc2C(=O)Nc2ccc(Cl)cc2)c(OCCNC(=O)OC(C)(C)C)c1 | CC(C)c1ccc(CNc2ncccc2C(=O)Nc2ccc(Cl)cc2)c(OCCN)c1 | null | null | FC(C(=O)O)(F)F | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | O=C(Nc1ccccc1)c1cccnc1NCc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[NH2;D1;+0:1] | 88 | [{"value": 88.0, "product": "NCCOC1=C(CNC2=NC=CC=C2C(=O)NC2=CC=C(C=C2)Cl)C=CC(=C1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.7, "product": "NCCOC1=C(CNC2=NC=CC=C2C(=O)NC2=CC=C(C=C2)Cl)C=CC(=C1)C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 2-[2-(N-Boc-Aminoethoxy)-4-isopropylbenzylamino]-N-(4-chlorophenyl)pyridine-3-carboxamide (0.02 g, 0.04 mmol) was dissolved in 2 mL of a 1:3 mixture of trifluoroacetic aicd:methylene chloride. The reaction mixture was stirred at room temperature for 30 min. The solvent was removed, and the material was purified by ion ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | HO- | FC(C(=O)O)(F)F | null | 0.5 | CC(C)c1ccc(CNc2ncccc2C(=O)Nc2ccc(Cl)cc2)c(OCCNC(=O)OC(C)(C)C)c1>FC(C(=O)O)(F)F>CC(C)c1ccc(CNc2ncccc2C(=O)Nc2ccc(Cl)cc2)c(OCCN)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5347db7719614c68834cfe16e6710679 | CC(C)(C)OC(=O)Nc1ccncc1C(=O)O.C[Si](C)(C)C=[N+]=[N-]>>COC(=O)c1cnccc1NC(=O)OC(C)(C)C | C(=O)(OC(C)(C)C)NC1=C(C=NC=C1)C(=O)O.C(C)(=O)O.C[Si](C)(C)C=[N+]=[N-]>>C(=O)(OC(C)(C)C)NC1=C(C=NC=C1)C(=O)OC | [OH:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][cH:9][c:10]1[NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18].C[Si](C)(C)[CH:1]=[N+]=[N-]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][cH:9][c:10]1[NH:11][C:12](=[O:13])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18] | CC(C)(C)OC(=O)Nc1ccncc1C(=O)O.C[Si](C)(C)C=[N+]=[N-] | COC(=O)c1cnccc1NC(=O)OC(C)(C)C | null | null | CO | Heteroatom Alkylation and Arylation | O-alkylation of carboxylic acids with diazo compounds | 39589be0e9a30df66714fe618d22a8ac0fb24901dbf2ead1ab33e31556c7ac64 | 8b539baf7aeb5ab868833e33306bad77200a853d562904197e13de2e27e229d7 | c1ccncc1 | C-[Si](-C)(-C)-[CH;D2;+0:1]=[N+]=[N-].[#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 | [{"value": 81.0, "product": "C(=O)(OC(C)(C)C)NC1=C(C=NC=C1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To a stirring suspension of 4-(Boc-amino)pyridine-3-carboxylic acid (1.04 g, 4.37 mmol) in methanol (3.5 mL) was added a 2 M solution of (trimethylsilyl)diazomethane in hexanes (3.5 mL, 7 mmol). After 15 min, acetic acid was added and the solvents were removed in vacuo. The residue was chromatographed over silica gel, ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Diazo.Silyl protective group | Ester | null | null | c1ccncc1 | Other | CO | null | 0.25 | CC(C)(C)OC(=O)Nc1ccncc1C(=O)O.C[Si](C)(C)C=[N+]=[N-]>CO>COC(=O)c1cnccc1NC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d0a6f6a08c924be985b821db55aa71fe | COC(=O)c1cnccc1NC(=O)OC(C)(C)C>>COC(=O)c1cnccc1N | C(=O)(OC(C)(C)C)NC1=C(C=NC=C1)C(=O)OC>>NC1=C(C=NC=C1)C(=O)OC | CC(C)(C)OC(=O)[NH:11][c:10]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][n:7][cH:8][cH:9]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][cH:9][c:10]1[NH2:11] | COC(=O)c1cnccc1NC(=O)OC(C)(C)C | COC(=O)c1cnccc1N | null | null | C(=O)(C(F)(F)F)O | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | c1ccncc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:[c:7]:1-[C:8](-[#8:9])=[O;D1;H0:10]>>[#8:9]-[C:8](=[O;D1;H0:10])-[c:7]1:[c:6]:[#7;a:5]:[c:4]:[c:3]:[c:2]:1-[NH2;D1;+0:1] | 92.8 | [{"value": 92.0, "product": "NC1=C(C=NC=C1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.8, "product": "NC1=C(C=NC=C1)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 45 | MINUTE | Methyl 4-(Boc-amino)pyridine-3-carboxylate (2.38 g, 9.4 mmol) was dissolved in TFA (20 mL) and the solution was allowed to stir for 45 min. The solvent was removed in vacuo and the residue was partitioned between 25% isopropanol in chloroform and satd aq sodium bicarbonate. The layers were separated and the aqueous pha... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccncc1 | HO- | C(=O)(C(F)(F)F)O | null | 0.75 | COC(=O)c1cnccc1NC(=O)OC(C)(C)C>C(=O)(C(F)(F)F)O>COC(=O)c1cnccc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a4e122a776584622b446483b34fbc154 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Cl)CC1.COC(=O)c1cnccc1N>>COC(=O)C1C=NC=CC1(NC(=O)c1ccccc1OC1CCN(C(=O)OC(C)(C)C)CC1)C(C)(C)C | NC1=C(C=NC=C1)C(=O)OC.ClCCl.C(C)(C)(C)C1=CC(=C(C(=O)Cl)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C.ClCCl.C(C)(C)N(C(C)C)CC>>C(C)(C)(C)C1(C(C=NC=C1)C(=O)OC)NC(C1=C(C=CC=C1)OC1CCN(CC1)C(=O)OC(C)(C)C)=O | Cl[C:12](=[O:13])[c:14]1[cH:15][cH:16][c:17]([C:34]([CH3:35])([CH3:36])[CH3:37])[cH:18][c:19]1[O:20][CH: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.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][n:7][cH:8][cH:9][c:10]1[NH2:11]>>[CH3:1][O:2][C:3](=[O:4])[CH:5]1[CH:6]=[N:7]... | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Cl)CC1.COC(=O)c1cnccc1N | COC(=O)C1C=NC=CC1(NC(=O)c1ccccc1OC1CCN(C(=O)OC(C)(C)C)CC1)C(C)(C)C | null | null | C(C)(=O)OCC | Acylation | OtherReaction | 4c40b4ac63ec434db0260e5e5e943e6184513743d3104c45e0ac97b2ecf8559b | 1fc2dd1a0c8f81d359eaece097d5f07348b604afb79f3effe317cf29392ea335 | O=C(NC1C=CN=CC1)c1ccccc1OC1CCNCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[c:5]:[c;H0;D3;+0:6](-[C;H0;D4;+0:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C;D1;H3:10]):[c:11]:[c:12]:1.[C;D1;H3:13]-[#8:14]-[C:15](=[O;D1;H0:16])-[c;H0;D3;+0:17]1:[cH;D2;+0:18]:[n;H0;D2;+0:19]:[cH;D2;+0:20]:[cH;D2;+0:21]:[c;H0;D3;+0:22]:1-[NH2;D1;+0:23]>>[C;D1;H3:13]-[#8:14]-[C:15](... | 66 | [{"value": 66.0, "product": "C(C)(C)(C)C1(C(C=NC=C1)C(=O)OC)NC(C1=C(C=CC=C1)OC1CCN(CC1)C(=O)OC(C)(C)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirring suspension of methyl 4-aminopyridine-3-carboxylate (0.10 g, 0.659 mmol) in dichloromethane (1 mL) was added a solution of 4-tert-butyl-2-(1-Boc-piperidin-4-yloxy)benzoyl chloride (1.3 mmol) in dichloromethane (6 mL), followed by N,N-diisopropylethylamine (0.15 mL, 0.8 mmol) and 4-N,N-dimethylaminopyridine... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Primary amine | Ester.Substituted imine.Secondary amide | c1ccccc1.c1ccncc1 | C1=CN=CCC1.c1ccccc1 | C1=CN=CCC1.c1ccccc1.C1CC[NH]CC1 | Other | C(C)(=O)OCC | null | 8 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Cl)CC1.COC(=O)c1cnccc1N>C(C)(=O)OCC>COC(=O)C1C=NC=CC1(NC(=O)c1ccccc1OC1CCN(C(=O)OC(C)(C)C)CC1)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7348ba2905634b879e85a0d88faa1132 | COC(=O)c1cnccc1NC(=O)c1ccc(C(C)(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>>CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2ccncc2C(=O)O)CC1 | [Li+].[OH-].C(C)(C)(C)C1=CC(=C(C(=O)NC2=C(C=NC=C2)C(=O)OC)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C.O.O>>C(C)(C)(C)C1=CC(=C(C(=O)NC2=C(C=NC=C2)C(=O)O)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C | C[O:34][C:32]([c:31]1[c:26]([NH:25][C:23]([c:22]2[c:13]([O:12][CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:36][CH2:35]3)[cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]2)=[O:24])[cH:27][cH:28][n:29][cH:30]1)=[O:33]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:... | COC(=O)c1cnccc1NC(=O)c1ccc(C(C)(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2ccncc2C(=O)O)CC1 | null | null | O1CCCC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Nc1ccncc1)c1ccccc1OC1CCNCC1 | 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] | 80.2 | [{"value": 80.0, "product": "C(C)(C)(C)C1=CC(=C(C(=O)NC2=C(C=NC=C2)C(=O)O)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 80.2, "product": "C(C)(C)(C)C1=CC(=C(C(=O)NC2=C(C=NC=C2)C(=O)O)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirring solution of methyl 4-[4-tert-butyl-2-(1-Boc-piperidin-4-yloxy)benzoylamino]pyridine-3-carboxylate (0.192 g, 0.376 mmol) in tetrahydrofuran (4 mL) was added water (1 mL), followed by a 1 M solution of LiOH in water (0.4 mL, 0.4 mmol). After stirring overnight, the solution was partially concentrated in vac... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]CC1.c1ccccc1.c1ccncc1 | Other | O1CCCC1 | null | 8 | COC(=O)c1cnccc1NC(=O)c1ccc(C(C)(C)C)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>O1CCCC1>CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2ccncc2C(=O)O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7f4dfec2d1b249969514a1e3303875f6 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2ccncc2C(=O)O)CC1>>CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2-c2nc3ccncc3c(=O)o2)CC1 | C(C)(C)(C)C1=CC(=C(C(=O)NC2=C(C=NC=C2)C(=O)O)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C.Cl.CN(CCCN=C=NCC)C>>C(C)(C)(C)C1=CC(=C(C=C1)C=1OC(C2=C(N1)C=CN=C2)=O)OC2CCN(CC2)C(=O)OC(C)(C)C | O[C:31]([c:30]1[c:25]([NH:24][C:23]([c:22]2[c:13]([O:12][CH:11]3[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:35][CH2:34]3)[cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]2)=[O:33])[cH:26][cH:27][n:28][cH:29]1)=[O:32]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH... | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2ccncc2C(=O)O)CC1 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2-c2nc3ccncc3c(=O)o2)CC1 | null | null | CN(C)C=O | Aromatic Heterocycle Formation | OtherReaction | 738fce1d0eb6fbbeb524f3efb6a269aaeb4cc42e45f8c3095f069eaec363b8f9 | c386cc4dfdcb50b87b14b7a3d3e77ff2ca728c923e8c9b97ba53184613a52138 | O=c1oc(-c2ccccc2OC2CCNCC2)nc2ccncc12 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]1:[c:4]:[#7;a:5]:[c:6]:[c:7]:[c:8]:1-[NH;D2;+0:9]-[C;H0;D3;+0:10](=[O;H0;D1;+0:11])-[c;H0;D3;+0:12](:[c:13]:[c:14]):[c:15](-[#8:16]):[c:17]>>[#8:16]-[c:15](:[c:17]):[c;H0;D3;+0:12](-[c;H0;D3;+0:10]1:[n;H0;D2;+0:9]:[c:8]2:[c:7]:[c:6]:[#7;a:5]:[c:4]:[c:3]:2:[c;H0;D3;+0:1](=[O;D1;H0:2])... | 84.1 | [{"value": 84.0, "product": "C(C)(C)(C)C1=CC(=C(C=C1)C=1OC(C2=C(N1)C=CN=C2)=O)OC2CCN(CC2)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.1, "product": "C(C)(C)(C)C1=CC(=C(C=C1)C=1OC(C2=C(N1)C=CN=C2)=O)OC2CCN(CC2)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirring solution of 4-[4-tert-butyl-2-(1-Boc-piperidin-4-yloxy)benzoylamino]pyridine-3-carboxylic acid (0.15 g, 0.30 mmol) in DMF (5 mL) was added 1-[3-(dimethyl-amino)propyl]-3-ethylcarbodiimide hydrochloride (0.077 g, 0.39 mmol). After stirring overnight, the solvent was removed in vacuo and the residue was dis... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amide | null | c1ccncc1 | c1nc2ccncc2co1 | C1CC[NH]CC1.c1ccccc1.c1nc2ccncc2co1 | HO- | CN(C)C=O | null | 8 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2ccncc2C(=O)O)CC1>CN(C)C=O>CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2-c2nc3ccncc3c(=O)o2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-537320c1c2dc45428e4e3c3c3aaf4570 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2-c2nc3ccncc3c(=O)o2)CC1.Nc1ccc(Cl)cn1>>CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2ccncc2C(=O)Nc2ccc(Cl)cn2)CC1 | NC1=NC=C(C=C1)Cl.C(C=C)[Mg]Cl.C(C)OCC.C(C)(C)(C)C1=CC(=C(C=C1)C=1OC(C2=C(N1)C=CN=C2)=O)OC2CCN(CC2)C(=O)OC(C)(C)C>>C(C)(C)(C)C1=CC(=C(C(=O)NC2=C(C=NC=C2)C(=O)NC2=NC=C(C=C2)Cl)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21][c:22]2-[c:23]2[o:24][c:32](=[O:33])[c:31]3[c:26]([n:25]2)[cH:27][cH:28][n:29][cH:30]3)[CH2:42][CH2:43]1.[NH2:34][c:35]1[cH:36][cH:37][c:38]([Cl:39])[cH:40][n:41]1>>[C... | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2-c2nc3ccncc3c(=O)o2)CC1.Nc1ccc(Cl)cn1 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2ccncc2C(=O)Nc2ccc(Cl)cn2)CC1 | null | null | C(C)(=O)OCC.C1CCOC1 | Acylation | OtherReaction | 01ef3ffd9dff64029b5e0e405490bcd195aa6c4c4b93124f80514842cfaec36a | 4accd3f274dad8ca7d44350b7d7da15181b5e5579c068528178b23416d2aea4a | O=C(Nc1ccccn1)c1cnccc1NC(=O)c1ccccc1OC1CCNCC1 | [#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[c;H0;D3;+0:5]1:[n;H0;D2;+0:6]:[c:7]2:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:2:[c;H0;D3;+0:13](=[O;D1;H0:14]):[o;H0;D2;+0:15]:1):[c:16]:[c:17].[NH2;D1;+0:18]-[c:19](:[c:20]):[#7;a:21]:[c:22]>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[C;H0;D3;+0:5](=[O;H0;D1;+0:15])-[NH;D2;+0:6]-[c:7]1:[c:8... | 72.4 | [{"value": 70.0, "product": "C(C)(C)(C)C1=CC(=C(C(=O)NC2=C(C=NC=C2)C(=O)NC2=NC=C(C=C2)Cl)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.4, "product": "C(C)(C)(C)C1=CC(=C(C(=O)NC2=C(C=NC=C2)C(=O)NC2=NC=C(C=C2)Cl)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCEN... | null | null | null | null | To a stirring solution of 2-amino-5-chloropyridine (0.055 g, 0.42 mmol) in THF (5 mL) at 0° C., was added a 1.0 M solution of allylmagnesium chloride in diethyl ether (0.4 mL, 0.4 mmol). To this solution was then added a solution of 2-[4-tert-butyl-2-(1-Boc-piperidin-4-yloxy)-phenyl]-4H-pyrido[4,3-d][1,3]oxazin-4-one (... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Secondary amide.Secondary amide | c1nc2ccncc2co1 | c1ccncc1 | C1CC[NH]CC1.c1ccccc1.c1ccncc1.c1ccncc1 | null | C(C)(=O)OCC.C1CCOC1 | null | null | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2-c2nc3ccncc3c(=O)o2)CC1.Nc1ccc(Cl)cn1>C(C)(=O)OCC.C1CCOC1>CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2ccncc2C(=O)Nc2ccc(Cl)cn2)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3f80ed626d8348359710fe0cba5b3db1 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2ccncc2C(=O)Nc2ccc(Cl)cn2)CC1>>CC(C)(C)c1ccc(C(=O)Nc2ccncc2C(=O)Nc2ccc(Cl)cn2)c(OC2CCNCC2)c1 | C(C)(C)(C)C1=CC(=C(C(=O)NC2=C(C=NC=C2)C(=O)NC2=NC=C(C=C2)Cl)C=C1)OC1CCN(CC1)C(=O)OC(C)(C)C.C1(=CC=CC=C1)OC.C(=O)(C(F)(F)F)O>>FC(C(=O)O)(F)F.C(C)(C)(C)C1=CC(=C(C(=O)NC2=C(C=NC=C2)C(=O)NC2=NC=C(C=C2)Cl)C=C1)OC1CCNCC1 | CC(C)(C)OC(=O)[N:33]1[CH2:32][CH2:31][CH:30]([O:29][c:28]2[c:8]([C:9](=[O:10])[NH:11][c:12]3[cH:13][cH:14][n:15][cH:16][c:17]3[C:18](=[O:19])[NH:20][c:21]3[cH:22][cH:23][c:24]([Cl:25])[cH:26][n:27]3)[cH:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[cH:36]2)[CH2:35][CH2:34]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][c... | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2ccncc2C(=O)Nc2ccc(Cl)cn2)CC1 | CC(C)(C)c1ccc(C(=O)Nc2ccncc2C(=O)Nc2ccc(Cl)cn2)c(OC2CCNCC2)c1 | null | null | ClCCl | Reduction | Boc amine deprotection | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | O=C(Nc1ccccn1)c1cnccc1NC(=O)c1ccccc1OC1CCNCC1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5] | 88 | [{"value": 88.0, "product": "FC(C(=O)O)(F)F.C(C)(C)(C)C1=CC(=C(C(=O)NC2=C(C=NC=C2)C(=O)NC2=NC=C(C=C2)Cl)C=C1)OC1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a stirring solution of 4-[4-tert-butyl-2-(1-Boc-piperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)pyridine-3-carboxamide (0.099 g, 0.163 mmol) and anisole (0.1 mL) in dichloromethane (5 mL) was added TFA (0.5 mL). After 2 h, the solvent was removed in vacuo and the residue was suspended in toluene and concentr... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.c1ccncc1.c1ccncc1.C1CCNCC1 | HO- | ClCCl | null | 2 | CC(C)(C)OC(=O)N1CCC(Oc2cc(C(C)(C)C)ccc2C(=O)Nc2ccncc2C(=O)Nc2ccc(Cl)cn2)CC1>ClCCl>CC(C)(C)c1ccc(C(=O)Nc2ccncc2C(=O)Nc2ccc(Cl)cn2)c(OC2CCNCC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2eff0da841654459882383e7c9b1b5c1 | COC(=O)c1ccc(O)cc1O.FCCBr>>COC(=O)c1ccc(OCCF)cc1O | OC1=C(C(=O)OC)C=CC(=C1)O.BrCCF.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>>FCCOC1=CC(=C(C(=O)OC)C=C1)O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([OH:9])[cH:13][c:14]1[OH:15].Br[CH2:10][CH2:11][F:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][F:12])[cH:13][c:14]1[OH:15] | COC(=O)c1ccc(O)cc1O.FCCBr | COC(=O)c1ccc(OCCF)cc1O | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[F;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[F;D1;H0:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 57.5 | CELSIUS | null | null | A mixture of methyl 2,4-dihydroxybenzoate (5.04 g, 30 mmol), 1-bromo-2-fluoroethane (4.18 g, 2.46 mL, 33 mmol), potassium carbonate (4.55 g, 33 mmol) and potassium iodide (1 g) in DMF (20 mL) was heated overnight at 55-60° C. before it was poured into water (150 mL). The resulting white precipitate was filtered, rediss... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | O.CN(C)C=O | 57.5 | null | COC(=O)c1ccc(O)cc1O.FCCBr>O.CN(C)C=O>COC(=O)c1ccc(OCCF)cc1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-124911f9618c472dbe489aba7f243e43 | CC(C)(C)OC(=O)N1CCC(O)CC1.COC(=O)c1ccc(OCCF)cc1O>>COC(=O)c1ccc(OCCF)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | FCCOC1=CC(=C(C(=O)OC)C=C1)O.C(C)(C)(C)OC(=O)N1CCC(CC1)O.N(=NC(=O)OCC)C(=O)OCC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)OCCF | O[CH:16]1[CH2:17][CH2:18][N:19]([C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:27][CH2:28]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][F:12])[cH:13][c:14]1[OH:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][F:12])[cH:13][c:14]1[O:15][CH:16]1[CH2:17][... | CC(C)(C)OC(=O)N1CCC(O)CC1.COC(=O)c1ccc(OCCF)cc1O | COC(=O)c1ccc(OCCF)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | a9e936b0e9135225700edbab1c7696738b7f1f0756494b6ceeeda63b184d572f | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1ccc(OC2CCNCC2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[O;H0;D2;+0:12]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:13] | 102.9 | [{"value": 102.9, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)OCCF", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure similar to that of Example 6-D, methyl 4-(2-fluoroethoxy)-2-hydroxybenzoate (3.6 g, 17.8 mmol), 1-tert-butoxycarbonyl-4-hydroxypiperidine (3.58 g, 17.8 mmol), and triphenylphosphine (5.60 g, 21.4 mmol) in THF (75 mL) is treated with diethyl azodicarboxylate (3.60 g, 17.8 mmol) in THF (15 mL) to afford... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HO- | C1CCOC1 | null | null | CC(C)(C)OC(=O)N1CCC(O)CC1.COC(=O)c1ccc(OCCF)cc1O>C1CCOC1>COC(=O)c1ccc(OCCF)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-648d187d3a16427b93e0cce86473ba35 | COC(=O)c1ccc(OCCF)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>>CC(C)(C)OC(=O)N1CCC(Oc2cc(OCCF)ccc2C(=O)O)CC1 | C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)OCCF.O[Li].O.O>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)O)C=CC(=C1)OCCF | C[O:25][C:23]([c:22]1[c:13]([O:12][CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:27][CH2:26]2)[cH:14][c:15]([O:16][CH2:17][CH2:18][F:19])[cH:20][cH:21]1)=[O:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([O:12][c:13]2[cH:14][c:15]([O:16][CH2:17][CH2... | COC(=O)c1ccc(OCCF)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | CC(C)(C)OC(=O)N1CCC(Oc2cc(OCCF)ccc2C(=O)O)CC1 | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(OC2CCNCC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 40 | [{"value": 40.0, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)O)C=CC(=C1)OCCF", "details": "PERCENTYIELD", "is_desired": false}, {"value": 39.3, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)O)C=CC(=C1)OCCF", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure similar to that of Example 6-E, methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(2-fluoroethoxy)benzoate (7.28 g) is hydrolyzed using LiOH.H2O (1.78 g, 2.2 equivalents), water (20 mL) and THF (60 mL) at 60-65° C. to afford the acid (2.76 g, 40%).
Conditions: See reaction.notes.procedure_details.
W... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]CC1.c1ccccc1 | Other | C1CCOC1 | null | null | COC(=O)c1ccc(OCCF)cc1OC1CCN(C(=O)OC(C)(C)C)CC1>C1CCOC1>CC(C)(C)OC(=O)N1CCC(Oc2cc(OCCF)ccc2C(=O)O)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-445ff504caa7472293b9a6f54b4d2ea7 | CC(C)(C)OC(=O)N1CCCC(CO)C1.CCOC(=O)N=NC(=O)OCC.O=C([O-])c1ccc(OCCF)cc1O>>COC(=O)c1ccc(OCCF)cc1OCC1CCCN(C(=O)OC(C)(C)C)C1 | FCCOC1=CC(=C(C(=O)[O-])C=C1)O.C(C)(C)(C)OC(=O)N1CC(CCC1)CO.N(=NC(=O)OCC)C(=O)OCC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)(C)(C)OC(=O)N1CC(CCC1)COC1=C(C(=O)OC)C=CC(=C1)OCCF | O[CH2:16][CH:17]1[CH2:18][CH2:19][CH2:20][N:21]([C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29]1.CCOC(=O)N=NC(=O)O[CH2:1]C.[O-:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][F:12])[cH:13][c:14]1[OH:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][F:12])[cH:13][c... | CC(C)(C)OC(=O)N1CCCC(CO)C1.CCOC(=O)N=NC(=O)OCC.O=C([O-])c1ccc(OCCF)cc1O | COC(=O)c1ccc(OCCF)cc1OCC1CCCN(C(=O)OC(C)(C)C)C1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 6998b76c1fb00648c00a2106cbf23f36aee9db18b229882ac92a6f575220302c | c25afff91d4c1e70d2e5ea98a0decb1c958ecc71eaf896f606fa5564ee4cf400 | c1ccc(OCC2CCCNC2)cc1 | C-C-O-C(=O)-N=N-C(=O)-O-[CH2;D2;+0:1]-C.O-[CH2;D2;+0:2]-[C:3](-[C:4])-[C:5]-[#7:6].[O-;H0;D1:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#7:6]-[C:5]-[C:3](-[CH2;D2;+0:2]-[O;H0;D2;+0:12]-[c:11](:[c:13]):[c:10]-[C:8](=[O;D1;H0:9])-[O;H0;D2;+0:7]-[CH3;D1;+0:1])-[C:4] | 120.6 | [{"value": 120.6, "product": "C(C)(C)(C)OC(=O)N1CC(CCC1)COC1=C(C(=O)OC)C=CC(=C1)OCCF", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure similar to that of Example 26-B, 4-(2-fluoroethoxy)-2-hydroxybenzoate (2.6 g, 12.8 mmol), 1-tert-butoxycarbonylpiperidin-3-ylmethanol (2.76 g, 12.8 mmol), and triphenylphosphine (4.02 g, 15.4 mmol) in THF (50 mL) is treated with diethyl azodicarboxylate (2.59 g, 12.8 mmol) in THF to afford methyl 2-(1... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Diazene.Primary alcohol.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1.C1CC[NH]CC1 | HO- | C1CCOC1 | null | null | CC(C)(C)OC(=O)N1CCCC(CO)C1.CCOC(=O)N=NC(=O)OCC.O=C([O-])c1ccc(OCCF)cc1O>C1CCOC1>COC(=O)c1ccc(OCCF)cc1OCC1CCCN(C(=O)OC(C)(C)C)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-02293026a49c475ba7ec60af6f3d7760 | COC(=O)c1ccc(OCCF)cc1OCC1CCCN(C(=O)OC(C)(C)C)C1>>CC(C)(C)OC(=O)N1CCCC(COc2cc(OCCF)ccc2C(=O)O)C1 | C(C)(C)(C)OC(=O)N1CC(CCC1)COC1=C(C(=O)OC)C=CC(=C1)OCCF.O[Li].O.O>>C(C)(C)(C)OC(=O)N1CC(CCC1)COC1=C(C(=O)O)C=CC(=C1)OCCF | C[O:27][C:25]([c:24]1[c:15]([O:14][CH2:13][CH:12]2[CH2:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:28]2)[cH:16][c:17]([O:18][CH2:19][CH2:20][F:21])[cH:22][cH:23]1)=[O:26]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][CH:12]([CH2:13][O:14][c:15]2[cH:16][... | COC(=O)c1ccc(OCCF)cc1OCC1CCCN(C(=O)OC(C)(C)C)C1 | CC(C)(C)OC(=O)N1CCCC(COc2cc(OCCF)ccc2C(=O)O)C1 | null | null | C1CCOC1 | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(OCC2CCCNC2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | null | [] | null | null | null | null | Using a procedure similar to that of Example 26-C, the ester is hydrolyzed using LiOH.H2O (1.50 g, 2.2 equivalents), water (20 mL) and THF (60 mL) to afford the acid (2.93 g, 59% for the two steps).
Conditions: See reaction.notes.procedure_details.
Workup: to afford the acid (2.93 g, 59% for the two steps) | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]CC1.c1ccccc1 | Other | C1CCOC1 | null | null | COC(=O)c1ccc(OCCF)cc1OCC1CCCN(C(=O)OC(C)(C)C)C1>C1CCOC1>CC(C)(C)OC(=O)N1CCCC(COc2cc(OCCF)ccc2C(=O)O)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3391cfa1a6a840eebbbe1fab055a94af | CC(C)(CO)CNC(=O)OC(C)(C)C.COC(=O)c1ccc(OCCF)cc1O>>COC(=O)c1ccc(OCCF)cc1OCC(C)(C)CNC(=O)OC(C)(C)C | FCCOC1=CC(=C(C(=O)OC)C=C1)O.C(C)(C)(C)OC(=O)NCC(CO)(C)C>>C(C)(C)(C)OC(=O)NCC(COC1=C(C(=O)OC)C=CC(=C1)OCCF)(C)C | O[CH2:16][C:17]([CH3:18])([CH3:19])[CH2:20][NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][F:12])[cH:13][c:14]1[OH:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][F:12])[cH:13][c:14]1[O:15][CH2:16][C:17]([C... | CC(C)(CO)CNC(=O)OC(C)(C)C.COC(=O)c1ccc(OCCF)cc1O | COC(=O)c1ccc(OCCF)cc1OCC(C)(C)CNC(=O)OC(C)(C)C | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[C;D1;H3:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[C;D1;H3:5]):[c:12] | 72 | [{"value": 72.0, "product": "C(C)(C)(C)OC(=O)NCC(COC1=C(C(=O)OC)C=CC(=C1)OCCF)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure similar to that of Example 26-B, methyl 4-(2-fluoroethoxy)-2-hydroxybenzoate (3.6 g, 17.8 mmol) is alkylated with 3-tert-butoxycarbonylamino-2,2-dimethylpropanol (3.62 g, 17.8 mmol) to afford methyl 2-(3-tert-butoxycarbonylamino-2,2-dimethylpropoxy)-4-(2-fluoroethoxy)benzoate (5.12 g).
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1 | HO- | null | null | null | CC(C)(CO)CNC(=O)OC(C)(C)C.COC(=O)c1ccc(OCCF)cc1O>>COC(=O)c1ccc(OCCF)cc1OCC(C)(C)CNC(=O)OC(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0fe4a2024130415982a1cf7bb40535a2 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](O)CC1.COC(=O)c1ccc(OCCF)cc1O>>COC(=O)c1ccc(OCCF)cc1O[C@@H]1CC[C@H](NC(=O)OC(C)(C)C)CC1 | FCCOC1=CC(=C(C(=O)OC)C=C1)O.C(C)(C)(C)OC(=O)N[C@@H]1CC[C@H](CC1)O.N(=NC(=O)OCC)C(=O)OCC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C)(C)(C)OC(=O)N[C@H]1CC[C@H](CC1)OC1=C(C(=O)OC)C=CC(=C1)OCCF | [OH:15][C@H:16]1[CH2:17][CH2:18][C@H:19]([NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]1.O[c:14]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][F:12])[cH:13]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][F:12])[cH:13][c:14]1[O:15][C@H:... | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](O)CC1.COC(=O)c1ccc(OCCF)cc1O | COC(=O)c1ccc(OCCF)cc1O[C@@H]1CC[C@H](NC(=O)OC(C)(C)C)CC1 | null | null | CCCCCC.C(C)(=O)OCC.C1CCOC1 | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | de817abd28aa0a6201a692784d613d548e53f67c49ed49b6eff382c8e9e7a9e4 | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1ccc(OC2CCCCC2)cc1 | O-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8]):[c:9].[C:10]-[C:11](-[OH;D1;+0:12])-[C:13]>>[C:10]-[C:11](-[O;H0;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5](=[O;D1;H0:6])-[#8:7]-[C;D1;H3:8]):[c:9])-[C:13] | 71.7 | [{"value": 71.7, "product": "C(C)(C)(C)OC(=O)N[C@H]1CC[C@H](CC1)OC1=C(C(=O)OC)C=CC(=C1)OCCF", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | Using a procedure similar to that of Example 6-D, methyl 4-(2-fluoroethoxy)-2-hydroxybenzoate (5.0 g, 24.75 mmol), trans-4-tert-butoxycarbonylaminocyclohexanol (5.02 g, 24.75 mmol), and triphenylphosphine (1.2 equivalents) in THF (125 mL) is treated with diethyl azodicarboxylate (1.3 equivalents) in THF (25 mL). After ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | c1ccccc1 | c1ccccc1 | c1ccccc1.C1CCCCC1 | HO- | CCCCCC.C(C)(=O)OCC.C1CCOC1 | null | 8 | CC(C)(C)OC(=O)N[C@@H]1CC[C@@H](O)CC1.COC(=O)c1ccc(OCCF)cc1O>CCCCCC.C(C)(=O)OCC.C1CCOC1>COC(=O)c1ccc(OCCF)cc1O[C@@H]1CC[C@H](NC(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a02efbc475594085be6d4557b60f84e4 | CC(C)(C)OC(=O)N1CCC(O)CC1.COC(=O)c1ccc(OCC(F)(F)F)cc1O>>COC(=O)c1ccc(OCC(F)(F)F)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | OC1=C(C(=O)OC)C=CC(=C1)OCC(F)(F)F.C(C)(C)(C)OC(=O)N1CCC(CC1)O>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)OCC(F)(F)F | O[CH:18]1[CH2:19][CH2:20][N:21]([C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:29][CH2:30]1.[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][C:11]([F:12])([F:13])[F:14])[cH:15][c:16]1[OH:17]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][C:11]([F:12])([F:13])[F:14])[cH:15][c... | CC(C)(C)OC(=O)N1CCC(O)CC1.COC(=O)c1ccc(OCC(F)(F)F)cc1O | COC(=O)c1ccc(OCC(F)(F)F)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | a9e936b0e9135225700edbab1c7696738b7f1f0756494b6ceeeda63b184d572f | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1ccc(OC2CCNCC2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[O;H0;D2;+0:12]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:13] | 82.6 | [{"value": 82.6, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)OCC(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure similar to that of Example 26-B, methyl 2-hydroxy-4-(2,2,2-trifluoroethoxy)benzoate (2.0 g, 7.99 mmol) is alkylated with 1-tert-butoxycarbonyl-4-hydroxypiperidine (1.61 g, 7.99 mmol) to afford methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(2,2,2-trifluoroethoxy)benzoate (2.86 g).
Conditions: See... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(O)CC1.COC(=O)c1ccc(OCC(F)(F)F)cc1O>>COC(=O)c1ccc(OCC(F)(F)F)cc1OC1CCN(C(=O)OC(C)(C)C)CC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-51306b4812214cf79eac7b994c37ae78 | COC(=O)c1ccc(O)cc1O.COCCBr>>COCCOc1ccc(C(=O)OC)c(O)c1 | OC1=C(C(=O)OC)C=CC(=C1)O.BrCCOC.C([O-])([O-])=O.[K+].[K+].[I-].[Na+]>>OC1=C(C(=O)OC)C=CC(=C1)OCCOC | [OH:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[O:12][CH3:13])[c:14]([OH:15])[cH:16]1.Br[CH2:4][CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[O:12][CH3:13])[c:14]([OH:15])[cH:16]1 | COC(=O)c1ccc(O)cc1O.COCCBr | COCCOc1ccc(C(=O)OC)c(O)c1 | null | null | [Cl-].[Na+].O.CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 57.5 | CELSIUS | null | null | A mixture of methyl 2,4-dihydroxybenzoate (5.04 g, 30 mmol), 1-bromo-2-methoxyethane (3.1 mL, 33 mmol), potassium carbonate (4.55 g, 33 mmol) and sodium iodide (1 g) in DMF (20 mL) was heated overnight at 55-60° C. before it was poured into brine (300 mL). The resulting mixture was extracted with ethyl acetate; and the... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1 | HBr | [Cl-].[Na+].O.CN(C)C=O | 57.5 | null | COC(=O)c1ccc(O)cc1O.COCCBr>[Cl-].[Na+].O.CN(C)C=O>COCCOc1ccc(C(=O)OC)c(O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ae2dc634d3044565838c9800d362b386 | CC(C)(C)OC(=O)N1CCC(O)CC1.COCCOc1ccc(C(=O)OC)c(O)c1>>COCCOc1ccc(C(=O)OC)c(OC2CCN(C(=O)OC(C)(C)C)CC2)c1 | OC1=C(C(=O)OC)C=CC(=C1)OCCOC.C(C)(C)(C)OC(=O)N1CCC(CC1)O>>C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)OCCOC | O[CH:16]1[CH2:17][CH2:18][N:19]([C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:27][CH2:28]1.[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[O:12][CH3:13])[c:14]([OH:15])[cH:29]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[O:12][CH3:13])[c:14]([O:15][CH:16... | CC(C)(C)OC(=O)N1CCC(O)CC1.COCCOc1ccc(C(=O)OC)c(O)c1 | COCCOc1ccc(C(=O)OC)c(OC2CCN(C(=O)OC(C)(C)C)CC2)c1 | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | a9e936b0e9135225700edbab1c7696738b7f1f0756494b6ceeeda63b184d572f | 776ba735002e33225fbc578943016110c2c43efefd97bfeea4ec3cc2e2e1532f | c1ccc(OC2CCNCC2)cc1 | O-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[OH;D1;+0:12]):[c:13]>>[#8:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[O;H0;D2;+0:12]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1):[c:13] | 89.6 | [{"value": 89.6, "product": "C(C)(C)(C)OC(=O)N1CCC(CC1)OC1=C(C(=O)OC)C=CC(=C1)OCCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure similar to that of Example 26-B, methyl 2-hydroxy-4-(2-methoxyethoxy)benzoate (2.72 g, 12.02 mmol) is alkylated with 1-tert-butoxycarbonyl-4-hydroxy-piperidine (2.44 g, 12.02 mmol) to afford methyl 2-(1-tert-butoxycarbonylpiperidin-4-yloxy)-4-(2-methoxyethoxy)benzoate (4.41 g).
Conditions: See reactio... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Aromatic alcohol | Ether | C1CC[NH]CC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(O)CC1.COCCOc1ccc(C(=O)OC)c(O)c1>>COCCOc1ccc(C(=O)OC)c(OC2CCN(C(=O)OC(C)(C)C)CC2)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c2dc5be7370c4e9b94725db4891a4666 | CC(C)(CO)CNC(=O)OC(C)(C)C.COCCOc1ccc(C(=O)OC)c(O)c1>>COCCOc1ccc(C(=O)OC)c(OCC(C)(C)CNC(=O)OC(C)(C)C)c1 | OC1=C(C(=O)OC)C=CC(=C1)OCCOC.C(C)(C)(C)OC(=O)NCC(CO)(C)C>>C(C)(C)(C)OC(=O)NCC(COC1=C(C(=O)OC)C=CC(=C1)OCCOC)(C)C | O[CH2:16][C:17]([CH3:18])([CH3:19])[CH2:20][NH:21][C:22](=[O:23])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28].[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[O:12][CH3:13])[c:14]([OH:15])[cH:29]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]([C:10](=[O:11])[O:12][CH3:13])[c:14]([O:15][CH2:1... | CC(C)(CO)CNC(=O)OC(C)(C)C.COCCOc1ccc(C(=O)OC)c(O)c1 | COCCOc1ccc(C(=O)OC)c(OCC(C)(C)CNC(=O)OC(C)(C)C)c1 | null | null | null | Heteroatom Alkylation and Arylation | Mitsunobu aryl ether | 86bfb73617450d22f9456ed5ce4d96a73f1f8fc0c016bebae57fda68e2da86a2 | 2258bd14c3b5449b92dc09cf9fa522f88d5071b4af20f7e968b60aa1ae6db0cf | c1ccccc1 | O-[CH2;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[C;D1;H3:5].[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[OH;D1;+0:11]):[c:12]>>[#8:6]-[C:7](=[O;D1;H0:8])-[c:9]:[c:10](-[O;H0;D2;+0:11]-[CH2;D2;+0:1]-[C:2](-[C:3])(-[C;D1;H3:4])-[C;D1;H3:5]):[c:12] | 85.6 | [{"value": 85.6, "product": "C(C)(C)(C)OC(=O)NCC(COC1=C(C(=O)OC)C=CC(=C1)OCCOC)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using a procedure similar to that of Example 26-B, methyl 2-hydroxy-4-(2-methoxyethoxy)benzoate (3.2 g, 14.14 mmol) is alkylated with 3-tert-butoxycarbonylamino-2,2-dimethylpropanol (2.88 g, 14.14 mmol) to afford methyl 2-(3-tert-butoxycarbonylamino-2,2-dimethylpropoxy)-4-(2-methoxyethoxy)benzoate (4.982 g) after purif... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Aromatic alcohol | Ether | null | null | c1ccccc1 | HO- | null | null | null | CC(C)(CO)CNC(=O)OC(C)(C)C.COCCOc1ccc(C(=O)OC)c(O)c1>>COCCOc1ccc(C(=O)OC)c(OCC(C)(C)CNC(=O)OC(C)(C)C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7fdc48bc0b414ef59a18e4908777305b | COCOc1cccc(C2(C)OCCO2)c1.O=C=O>>COCOc1cc(C2(C)OCCO2)ccc1C(=O)O | C(=O)=O.CC1(OCCO1)C=1C=C(C=CC1)OCOC.C(C)(C)(C)[Li]>>CC1(OCCO1)C1=CC(=C(C(=O)O)C=C1)OCOC | [CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][c:7]([C:8]2([CH3:9])[O:10][CH2:11][CH2:12][O:13]2)[cH:14][cH:15][cH:16]1.[C:17](=[O:18])=[O:19]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][c:7]([C:8]2([CH3:9])[O:10][CH2:11][CH2:12][O:13]2)[cH:14][cH:15][c:16]1[C:17](=[O:18])[OH:19] | COCOc1cccc(C2(C)OCCO2)c1.O=C=O | COCOc1cc(C2(C)OCCO2)ccc1C(=O)O | null | null | CCOCC | Acylation | OtherReaction | d512242205ca0afb7920772ddd09825654068f093b5b2190929ae26db328221a | f2fa2063dd26da08ea200eb6cbb3037b91013a82352a2b60120e98f9e54cbd88 | c1ccc(C2OCCO2)cc1 | [#8:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6].[O;D1;H0:7]=[C;H0;D2;+0:8]=[O;H0;D1;+0:9]>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[C;H0;D3;+0:8](=[O;D1;H0:7])-[OH;D1;+0:9]):[c:5]:[c:6] | null | [] | 10 | CELSIUS | null | null | To a solution of methoxymethyl 3-(2-methyl-1,3-dioxolan-2-yl)phenyl ether (8.16 g, 36.4 mmol) in ether (200 mL) was added dropwise tert-butyl lithium (1.7 M solution, 26.8 mL, 1.25 equivalents) at −5 to −10° C. The reaction mixture was stirred 15 min before carbon dioxide gas was bubbled in for 5 min. The reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Carbon dioxide | Carboxylic acid | c1ccccc1 | c1ccccc1 | c1ccccc1.C1COCO1 | null | CCOCC | 10 | null | COCOc1cccc(C2(C)OCCO2)c1.O=C=O>CCOCC>COCOc1cc(C2(C)OCCO2)ccc1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-506d020f05dc4e06926c5a703d23fbaa | COCOc1cc(C2(C)OCCO2)ccc1C(=O)Nc1cccnc1C(=O)Nc1ccc(Cl)cn1>>CC(=O)c1ccc(C(=O)Nc2cccnc2C(=O)Nc2ccc(Cl)cn2)c(O)c1 | ClC=1C=CC(=NC1)NC(=O)C1=NC=CC=C1NC(C1=C(C=C(C=C1)C1(OCCO1)C)OCOC)=O.C(=O)(C(F)(F)F)O>>C(C)(=O)C1=CC(=C(C(=O)NC=2C(=NC=CC2)C(=O)NC2=NC=C(C=C2)Cl)C=C1)O | COC[O:28][c:27]1[c:7]([C:8](=[O:9])[NH:10][c:11]2[cH:12][cH:13][cH:14][n:15][c:16]2[C:17](=[O:18])[NH:19][c:20]2[cH:21][cH:22][c:23]([Cl:24])[cH:25][n:26]2)[cH:6][cH:5][c:4]([C:2]2([CH3:1])OCC[O:3]2)[cH:29]1>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[NH:10][c:11]2[cH:12][cH:13][cH:14][n:15][c:16]2[C:17]... | COCOc1cc(C2(C)OCCO2)ccc1C(=O)Nc1cccnc1C(=O)Nc1ccc(Cl)cn1 | CC(=O)c1ccc(C(=O)Nc2cccnc2C(=O)Nc2ccc(Cl)cn2)c(O)c1 | null | null | O | Miscellaneous | OtherReaction | 6c74714319c018934ab052dab2883ec1715618294b3a59459bcb05e410cf5362 | 3448fc7deb63a7904c2d5aaa772e6ddc22b9edb260ac097cd876b0f3e36979b0 | O=C(Nc1cccnc1C(=O)Nc1ccccn1)c1ccccc1 | C-O-C-[O;H0;D2;+0:1]-[c:2](:[c:3]:[c:4](-[C;H0;D4;+0:5]1(-[C;D1;H3:6])-O-C-C-[O;H0;D2;+0:7]-1):[c:8]):[c:9]-[C:10](-[#7:11])=[O;D1;H0:12]>>[#7:11]-[C:10](=[O;D1;H0:12])-[c:9]:[c:2](-[OH;D1;+0:1]):[c:3]:[c:4](-[C;H0;D3;+0:5](-[C;D1;H3:6])=[O;H0;D1;+0:7]):[c:8] | 18.6 | [{"value": 18.6, "product": "C(C)(=O)C1=CC(=C(C(=O)NC=2C(=NC=CC2)C(=O)NC2=NC=C(C=C2)Cl)C=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | N-(5-Chloropyridin-2-yl)-3-[4-(2-methyl-1,3-dioxolan-2-yl)-2-(methoxymethoxy)benzoylamino]pyridine-2-carboxamide (3.10 g) is treated with a solution of TFA (20 mL) and water (20 mL) for 2 h before the solution is evaporated. The residue is slurried with ethyl acetate to provide a solid which is collected and washed. Th... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Ketone.Aromatic alcohol | C1COCO1 | null | c1ccccc1.c1ccncc1.c1ccncc1 | HO- | O | null | null | COCOc1cc(C2(C)OCCO2)ccc1C(=O)Nc1cccnc1C(=O)Nc1ccc(Cl)cn1>O>CC(=O)c1ccc(C(=O)Nc2cccnc2C(=O)Nc2ccc(Cl)cn2)c(O)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ca2ea7aa7d104799bcd14d3dc93f50d2 | CC(=O)c1cccc(O)c1.COCCl>>COCOc1cccc(C(C)=O)c1 | ClCOC.CC(=O)C=1C=CC=C(C1)O.C(C)(C)N(C(C)C)CC>>COCOC1=CC(=CC=C1)C(C)=O | [OH:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([CH3:11])=[O:12])[cH:13]1.Cl[CH2:3][O:2][CH3:1]>>[CH3:1][O:2][CH2:3][O:4][c:5]1[cH:6][cH:7][cH:8][c:9]([C:10]([CH3:11])=[O:12])[cH:13]1 | CC(=O)c1cccc(O)c1.COCCl | COCOc1cccc(C(C)=O)c1 | null | null | C(Cl)Cl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 6e90ffbf0683e1a3ee55c5e3ea453aefc5ddd369c0150ed0150f9546d7e47f4f | efd670663709b79afcad1306da9f69b33a0147cfa3639ca4c0b54b35ef4b1852 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[#8:2]-[C;D1;H3:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:3]-[#8:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 64 | [{"value": 64.0, "product": "COCOC1=CC(=CC=C1)C(C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.0, "product": "COCOC1=CC(=CC=C1)C(C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | To a stirred solution of 3-hydroxyacetophenone (20.40 g, 150 mmol) in CH2Cl2 (450 mL) at 0° C. under N2 was added N,N-diisopropylethylamine (52.25 mL, 300 mmol) followed by methyl chloromethyl ether (MOM chloride) (13.67 mL, 180 mmol) over a period of 30 min. The reaction was stirred at 0° C. for 30 min and then at roo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ether.Aromatic alcohol | Ether.Ether | null | null | c1ccccc1 | HCl | C(Cl)Cl | 0 | 0.5 | CC(=O)c1cccc(O)c1.COCCl>C(Cl)Cl>COCOc1cccc(C(C)=O)c1 |
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