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-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7b37c31faaef4c5bb1868f6f9352f189 | CC(C)(C)c1ccc(CON)cc1.COc1c(Cl)ccnc1C>>COc1c(NOCc2ccc(C(C)(C)C)cc2)ccnc1C | ClC1=C(C(=NC=C1)C)OC.C(C)(C)(C)C1=CC=C(CON)C=C1>>C(C)(C)(C)C1=CC=C(CONC2=C(C(=NC=C2)C)OC)C=C1 | [NH2:5][O:6][CH2:7][c:8]1[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17]1.Cl[c:4]1[c:3]([O:2][CH3:1])[c:21]([CH3:22])[n:20][cH:19][cH:18]1>>[CH3:1][O:2][c:3]1[c:4]([NH:5][O:6][CH2:7][c:8]2[cH:9][cH:10][c:11]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17]2)[cH:18][cH:19][n:20][c:21]1[CH3:22] | CC(C)(C)c1ccc(CON)cc1.COc1c(Cl)ccnc1C | COc1c(NOCc2ccc(C(C)(C)C)cc2)ccnc1C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CONc2ccncc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C;D1;H3:6]):[c:7]:1-[#8:8].[C:9]-[#8:10]-[NH2;D1;+0:11]>>[#8:8]-[c:7]1:[c:5](-[C;D1;H3:6]):[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:11]-[#8:10]-[C:9] | 80 | [{"value": 80.0, "product": "C(C)(C)(C)C1=CC=C(CONC2=C(C(=NC=C2)C)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared analogously to Example 1 from 4-chloro-3-methoxy-2-methylpyridine and O-(4-tert-butylbenzyl)hydroxylamine. Yield: 80%; m.p.: 113° C.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | null | null | null | CC(C)(C)c1ccc(CON)cc1.COc1c(Cl)ccnc1C>>COc1c(NOCc2ccc(C(C)(C)C)cc2)ccnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a05cf5e0c43f4ae0a2ddb5d7e074dffb | COc1c(NOCc2ccccc2)ccnc1C.Cc1ccc(S(=O)(=O)OC2CCC3(CC2)OCC(C)(C)CO3)cc1>>COc1c(N(OCc2ccccc2)C2CCC3(CC2)OCC(C)(C)CO3)ccnc1C | C(C1=CC=CC=C1)ONC1=C(C(=NC=C1)C)OC.[H-].[Na+].CC1(COC2(OC1)CCC(CC2)OS(=O)(=O)C2=CC=C(C)C=C2)C.[H][H]>>C(C1=CC=CC=C1)ON(C1CCC2(OCC(CO2)(C)C)CC1)C1=C(C(=NC=C1)C)OC | [CH3:1][O:2][c:3]1[c:4]([NH:5][O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:27][cH:28][n:29][c:30]1[CH3:31].Cc1ccc(S(=O)(=O)O[CH:14]2[CH2:15][CH2:16][C:17]3([CH2:18][CH2:19]2)[O:20][CH2:21][C:22]([CH3:23])([CH3:24])[CH2:25][O:26]3)cc1>>[CH3:1][O:2][c:3]1[c:4]([N:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:... | COc1c(NOCc2ccccc2)ccnc1C.Cc1ccc(S(=O)(=O)OC2CCC3(CC2)OCC(C)(C)CO3)cc1 | COc1c(N(OCc2ccccc2)C2CCC3(CC2)OCC(C)(C)CO3)ccnc1C | null | null | CS(=O)C.C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 1ed5ab0235ed7383317ad877ff9509533e75fb953436d99ed30f9e668f7ef4f8 | 71b4ac4449ece5e0df64e56caf0f1cbac76e83f802a92104cfb6c6c861b6a71c | c1ccc(CON(c2ccncc2)C2CCC3(CC2)OCCCO3)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]):c:c:1.[C:6]-[#8:7]-[NH;D2;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[C:3]-[C:2]-[CH;D3;+0:1](-[N;H0;D3;+0:8](-[#8:7]-[C:6])-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1)-[C:4]-[C:5] | null | [] | 50 | CELSIUS | 4 | HOUR | 7.3 g of 4-(O-benzylhydroxylamino)-3-methoxy-2-methylpyridine in 30 ml of absolute DMSO are deprotonated under N2 using 0.9 g of sodium hydride (80% strength). After evolution of hydrogen has ended, 11.7 g of 3,3-dimethyl-9-tosyloxy-1,5-dioxaspiro[5.5]undecane are added in 50 ml of absolute THF. The mixture is stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary amine | Tertiary amine | c1ccccc1.C1CCC2(CC1)OCCCO2 | C1CCC2(CC1)OCCCO2 | c1ccncc1.c1ccccc1.C1CCC2(CC1)OCCCO2 | TsOH.HO- | CS(=O)C.C1CCOC1 | 50 | 4 | COc1c(NOCc2ccccc2)ccnc1C.Cc1ccc(S(=O)(=O)OC2CCC3(CC2)OCC(C)(C)CO3)cc1>CS(=O)C.C1CCOC1>COc1c(N(OCc2ccccc2)C2CCC3(CC2)OCC(C)(C)CO3)ccnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d2942481069b43c48c9121e0d8415d47 | COc1c(NOCc2ccccc2)ccnc1C.Cc1ccc(S(=O)(=O)OC2CCC3(CC2)OCCO3)cc1>>COc1c(N(OCc2ccccc2)C2CCC3(CC2)OCCO3)ccnc1C | C(C1=CC=CC=C1)ONC1=C(C(=NC=C1)C)OC.S(=O)(=O)(C1=CC=C(C)C=C1)OC1CCC2(OCCO2)CC1>>C(C1=CC=CC=C1)ON(C1CCC2(OCCO2)CC1)C1=C(C(=NC=C1)C)OC | [CH3:1][O:2][c:3]1[c:4]([NH:5][O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[cH:24][cH:25][n:26][c:27]1[CH3:28].Cc1ccc(S(=O)(=O)O[CH:14]2[CH2:15][CH2:16][C:17]3([CH2:18][CH2:19]2)[O:20][CH2:21][CH2:22][O:23]3)cc1>>[CH3:1][O:2][c:3]1[c:4]([N:5]([O:6][CH2:7][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH:14]2[CH2:1... | COc1c(NOCc2ccccc2)ccnc1C.Cc1ccc(S(=O)(=O)OC2CCC3(CC2)OCCO3)cc1 | COc1c(N(OCc2ccccc2)C2CCC3(CC2)OCCO3)ccnc1C | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 0f6ed1b48d8acfd9004cc562b036ac7f9d6a1b5a008aba33ebadbb706b113a22 | 71b4ac4449ece5e0df64e56caf0f1cbac76e83f802a92104cfb6c6c861b6a71c | c1ccc(CON(c2ccncc2)C2CCC3(CC2)OCCO3)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]):c:c:1.[C:6]-[#8:7]-[NH;D2;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[C:3]-[C:2]-[CH;D3;+0:1](-[N;H0;D3;+0:8](-[#8:7]-[C:6])-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1)-[C:4]-[C:5] | 70 | [{"value": 70.0, "product": "C(C1=CC=CC=C1)ON(C1CCC2(OCCO2)CC1)C1=C(C(=NC=C1)C)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Prepared analogously to Example 5 from 4-(O-benzylhydroxylamino)-3-methoxy-2-methylpyridine and 8-tosyloxy-1,4-dioxaspiro[4.5]decane. Yield: 70%
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary amine | Tertiary amine | c1ccccc1.C1CCC2(CC1)OCCO2 | C1CCC2(CC1)OCCO2 | c1ccncc1.c1ccccc1.C1CCC2(CC1)OCCO2 | TsOH.HO- | null | null | null | COc1c(NOCc2ccccc2)ccnc1C.Cc1ccc(S(=O)(=O)OC2CCC3(CC2)OCCO3)cc1>>COc1c(N(OCc2ccccc2)C2CCC3(CC2)OCCO3)ccnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f4dba46589654bd6a818f29b87cc4306 | COc1c(N(OCc2ccccc2)C2CCC3(CC2)OCC(C)(C)CO3)ccnc1C>>COc1c(NC2CCC3(CC2)OCC(C)(C)CO3)ccnc1C | C(C1=CC=CC=C1)ON(C1CCC2(OCC(CO2)(C)C)CC1)C1=C(C(=NC=C1)C)OC>>CC1(COC2(OC1)CCC(CC2)NC2=C(C(=NC=C2)C)OC)C | c1ccc(CO[N:5]([c:4]2[c:3]([O:2][CH3:1])[c:22]([CH3:23])[n:21][cH:20][cH:19]2)[CH:6]2[CH2:7][CH2:8][C:9]3([CH2:10][CH2:11]2)[O:12][CH2:13][C:14]([CH3:15])([CH3:16])[CH2:17][O:18]3)cc1>>[CH3:1][O:2][c:3]1[c:4]([NH:5][CH:6]2[CH2:7][CH2:8][C:9]3([CH2:10][CH2:11]2)[O:12][CH2:13][C:14]([CH3:15])([CH3:16])[CH2:17][O:18]3)[cH:... | COc1c(N(OCc2ccccc2)C2CCC3(CC2)OCC(C)(C)CO3)ccnc1C | COc1c(NC2CCC3(CC2)OCC(C)(C)CO3)ccnc1C | null | [Ni] | CO | Reduction | Hydrogenolysis of tertiary amines | 215d104343a7b35de5be990c5f5f235e56ba596d2e063a631da9494ea311dc2b | bcb9bfb3b7e1d1e34dc71b339ec9a6091906ae73cd7793ace40af94d3849dabf | c1cc(NC2CCC3(CC2)OCCCO3)ccn1 | [C:1]-[C:2](-[N;H0;D3;+0:3](-O-C-c1:c:c:c:c:c:1)-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1)-[C:10]>>[C:1]-[C:2](-[NH;D2;+0:3]-[c:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1)-[C:10] | null | [] | null | null | null | null | 6.5 g of 4-[O-benzyl-N-(3,3-dimethyl-1,5-dioxaspiro[5.5]undec-9-yl)hydroxylamino]-3-methoxy-2-methylpyridine in 70 ml of methanol are hydrogenated using 2 g of Raney nickel at normal pressure until absorption of hydrogen is complete. After filtering, the filtrate is concentrated and the product is dissolved in diisopro... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1 | null | c1ccncc1.C1CCC2(CC1)OCCCO2 | HO- | [Ni].CO | null | null | COc1c(N(OCc2ccccc2)C2CCC3(CC2)OCC(C)(C)CO3)ccnc1C>[Ni].CO>COc1c(NC2CCC3(CC2)OCC(C)(C)CO3)ccnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-87cd3f597261426bbf9068b66cd80964 | COc1c(NC2CCC3(CC2)OCCO3)ccnc1C>>COc1c(NC2CCC(=O)CC2)ccnc1C | Cl.O1CCOC12CCC(CC2)NC2=C(C(=NC=C2)C)OC>>Cl.O=C1CCC(CC1)NC1=C(C(=NC=C1)C)OC | C1C[O:10][C:9]2(O1)[CH2:8][CH2:7][CH:6]([NH:5][c:4]1[c:3]([O:2][CH3:1])[c:16]([CH3:17])[n:15][cH:14][cH:13]1)[CH2:12][CH2:11]2>>[CH3:1][O:2][c:3]1[c:4]([NH:5][CH:6]2[CH2:7][CH2:8][C:9](=[O:10])[CH2:11][CH2:12]2)[cH:13][cH:14][n:15][c:16]1[CH3:17] | COc1c(NC2CCC3(CC2)OCCO3)ccnc1C | COc1c(NC2CCC(=O)CC2)ccnc1C | null | null | C(=O)O | Miscellaneous | Ketal hydrolysis to ketone | 7165849453c1f3f22c37497ec202aa2a6a319b018b3ae9fffa16fa9182ebd128 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1CCC(Nc2ccncc2)CC1 | [C:1]-[C:2]-[C;H0;D4;+0:3]1(-O-C-C-[O;H0;D2;+0:4]-1)-[C:5]-[C:6]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[C:5]-[C:6] | null | [] | null | null | null | null | 27.3 g of 4-(1,4-dioxaspiro[4.5]dec-8-ylamino)-3-methoxy-2-methylpyridine hydrochloride are stirred with 400 ml of formic acid for 4 hours. The residue which remains after concentrating in vacuo is dissolved in methylene chloride and shaken with 2N NaOH. The methylene chloride phase is concentrated, the residue is diss... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1CCC2(CC1)OCCO2 | C1CCCCC1 | c1ccncc1.C1CCCCC1 | HO- | C(=O)O | null | null | COc1c(NC2CCC3(CC2)OCCO3)ccnc1C>C(=O)O>COc1c(NC2CCC(=O)CC2)ccnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7b74a27dcc2940b5b3a704ddbd2de98d | COc1c(NC2CCC(=O)CC2)ccnc1C.NOCc1ccccc1>>COc1c(NC2CCC(=NOCc3ccccc3)CC2)ccnc1C | O.O=C1CCC(CC1)NC1=C(C(=NC=C1)C)OC.C(C1=CC=CC=C1)ON.C(C)(=O)OCC.CO.O>>C(C1=CC=CC=C1)ON=C1CCC(CC1)NC1=C(C(=NC=C1)C)OC | O=[C:9]1[CH2:8][CH2:7][CH:6]([NH:5][c:4]2[c:3]([O:2][CH3:1])[c:24]([CH3:25])[n:23][cH:22][cH:21]2)[CH2:20][CH2:19]1.[NH2:10][O:11][CH2:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1>>[CH3:1][O:2][c:3]1[c:4]([NH:5][CH:6]2[CH2:7][CH2:8][C:9](=[N:10][O:11][CH2:12][c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[CH2:19][CH2:20... | COc1c(NC2CCC(=O)CC2)ccnc1C.NOCc1ccccc1 | COc1c(NC2CCC(=NOCc3ccccc3)CC2)ccnc1C | null | null | C1(=CC=CC=C1)C | Heteroatom Alkylation and Arylation | OtherReaction | b123293a415ce6152ab74c524d488242b27263f8777086f636c68871a471cfa1 | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | c1ccc(CON=C2CCC(Nc3ccncc3)CC2)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[C:6]-[#8:7]-[NH2;D1;+0:8]>>[C:6]-[#8:7]-[N;H0;D2;+0:8]=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5] | null | [] | null | null | null | null | 2 g of 4-(4-oxocyclohexylamino)-3-methoxy-2-methylpyridine and 1.2 g O-benzylhydroxylamine are boiled in toluene in a water separator until liberation of water has ended. The product is isolated by column chromatography (ethyl acetate/methanol 9:1; silica gel). 1.8 g=53%
Conditions: See reaction.notes.procedure_details... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | C1CCCCC1 | C1CCCCC1 | c1ccncc1.C1CCCCC1.c1ccccc1 | HO- | C1(=CC=CC=C1)C | null | null | COc1c(NC2CCC(=O)CC2)ccnc1C.NOCc1ccccc1>C1(=CC=CC=C1)C>COc1c(NC2CCC(=NOCc3ccccc3)CC2)ccnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-13d9fefea0ad416fb3ed3b3104651c13 | COc1c(NC2CCC(=O)CC2)ccnc1C.c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>>COc1c(NC2CCC(=Cc3ccccc3)CC2)ccnc1C | O.[Br-].C(C1=CC=CC=C1)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.C(CCC)[Li].O=C1CCC(CC1)NC1=C(C(=NC=C1)C)OC>>C(C1=CC=CC=C1)=C1CCC(CC1)NC1=C(C(=NC=C1)C)OC | O=[C:9]1[CH2:8][CH2:7][CH:6]([NH:5][c:4]2[c:3]([O:2][CH3:1])[c:22]([CH3:23])[n:21][cH:20][cH:19]2)[CH2:18][CH2:17]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)cc1>>[CH3:1][O:2][c:3]1[c:4]([NH:5][CH:6]2[CH2:7][CH2:8][C:9](=[CH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[CH2:17]... | COc1c(NC2CCC(=O)CC2)ccnc1C.c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | COc1c(NC2CCC(=Cc3ccccc3)CC2)ccnc1C | null | null | CS(=O)C.CCCCCC.COCCOC | C-C Coupling | Wittig with Phosphonium | 4ace91bfe286d7308b684482c14d0e07094c3e16f8d78c7715341add0f69a6d3 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | C(=C1CCC(Nc2ccncc2)CC1)c1ccccc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[c:6]:[c:7](-[CH2;D2;+0:8]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1):[c:9]>>[C:3]-[C:2]-[C;H0;D3;+0:1](=[CH;D2;+0:8]-[c:7](:[c:6]):[c:9])-[C:4]-[C:5] | null | [] | null | null | null | null | 7.8 g of benzyltriphenylphosphonium bromide in 50 ml of ethylene glycol dimethyl ether are deprotonated at 10° to 20° C. using 11 ml of 1.6 molar butyllithium solution in hexane. After 30 minutes 1.3 g of 4-(4-oxocyclohexylamino)-3-methoxy-2-methylpyridine are added dropwise in 10 ml of DMSO. After 5 hours at 40° to 50... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1CCCCC1.c1ccccc1.c1ccccc1.c1ccccc1 | C1CCCCC1 | c1ccncc1.C1CCCCC1.c1ccccc1 | HO- | CS(=O)C.CCCCCC.COCCOC | null | null | COc1c(NC2CCC(=O)CC2)ccnc1C.c1ccc(C[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>CS(=O)C.CCCCCC.COCCOC>COc1c(NC2CCC(=Cc3ccccc3)CC2)ccnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-77b579259b0e47c2ac2dc691717deb93 | CC(C)(C)c1ccc(CBr)cc1.COc1c(NC2CCC(=O)CC2)ccnc1C>>COc1c(N(CC2=CCC(O)(C(C)(C)C)C=C2)C2CCCCC2)ccnc1C | Cl.O=C1CCC(CC1)NC1=C(C(=NC=C1)C)OC.C1CCOC1.[Mg].C(C)(C)(C)C1=CC=C(CBr)C=C1>>OC1(CC=C(CN(C2=C(C(=NC=C2)C)OC)C2CCCCC2)C=C1)C(C)(C)C | Br[CH2:6][c:7]1[cH:8][cH:9][c:10]([C:12]([CH3:13])([CH3:14])[CH3:15])[cH:16][cH:17]1.[CH3:1][O:2][c:3]1[c:4]([NH:5][CH:18]2[CH2:19][CH2:20][C:21](=[O:11])[CH2:22][CH2:23]2)[cH:24][cH:25][n:26][c:27]1[CH3:28]>>[CH3:1][O:2][c:3]1[c:4]([N:5]([CH2:6][C:7]2=[CH:8][CH2:9][C:10]([OH:11])([C:12]([CH3:13])([CH3:14])[CH3:15])[CH... | CC(C)(C)c1ccc(CBr)cc1.COc1c(NC2CCC(=O)CC2)ccnc1C | COc1c(N(CC2=CCC(O)(C(C)(C)C)C=C2)C2CCCCC2)ccnc1C | null | null | CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | b4d889531d9ddb6a958bab05dde428abf42cb7bd1998285af822f1f407851945 | 23a4c72a0299e9ab2af725abaf399ead2493921ab1df5fa49643c4c5ff36720f | C1=CC(CN(c2ccncc2)C2CCCCC2)=CCC1 | Br-[CH2;D2;+0:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:[cH;D2;+0:4]:[c;H0;D3;+0:5](-[C:6](-[C;D1;H3:7])(-[C;D1;H3:8])-[C;D1;H3:9]):[cH;D2;+0:10]:[cH;D2;+0:11]:1.[O;H0;D1;+0:12]=[C;H0;D3;+0:13]1-[C:14]-[C:15]-[C:16](-[NH;D2;+0:17]-[c:18]2:[c:19]:[c:20]:[#7;a:21]:[c:22]:[c:23]:2)-[C:24]-[C:25]-1>>[C;D1;H3:7]-[C:6](-[C;D1;H3:8])(-... | null | [] | null | null | null | null | A Grignard solution is prepared from 1.2 g of magnesium and 12.9 g of 90% strength 4-tert-butylbenzyl bromide in 100 ml of abs. ether. 2.9 g of 4-(4-oxocyclohexylamino)-3-methoxy-2-methylpyridine in 50 ml of absolute THF are added dropwise to this solution. After 17 hours at room temperature it is acidified with 25 ml ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Secondary amine | Tertiary alcohol.Tertiary amine | c1ccccc1.C1CCCCC1 | C1=CCCC=C1.C1CCCCC1 | c1ccncc1.C1=CCCC=C1.C1CCCCC1 | Br- | CCOCC | null | null | CC(C)(C)c1ccc(CBr)cc1.COc1c(NC2CCC(=O)CC2)ccnc1C>CCOCC>COc1c(N(CC2=CCC(O)(C(C)(C)C)C=C2)C2CCCCC2)ccnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8babbf86aa35457596df795b424dbf27 | CCCCCCCCBr.COc1c(NC2CCC(=O)CC2)ccnc1C>>CCCCC(O)(CCC)N(c1ccnc(C)c1OC)C1CCCCC1 | Cl.[Mg].C(CCCCCCC)Br.C1CCOC1.O=C1CCC(CC1)NC1=C(C(=NC=C1)C)OC.C1CCOC1>>OC(CCC)(CCCC)N(C1=C(C(=NC=C1)C)OC)C1CCCCC1 | Br[CH2:9][CH2:8][CH2:7][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[O:6]=[C:23]1[CH2:22][CH2:21][CH:20]([NH:10][c:11]2[cH:12][cH:13][n:14][c:15]([CH3:16])[c:17]2[O:18][CH3:19])[CH2:25][CH2:24]1>>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]([OH:6])([CH2:7][CH2:8][CH3:9])[N:10]([c:11]1[cH:12][cH:13][n:14][c:15]([CH3:16])[c:17]1[O:18][CH3:1... | CCCCCCCCBr.COc1c(NC2CCC(=O)CC2)ccnc1C | CCCCC(O)(CCC)N(c1ccnc(C)c1OC)C1CCCCC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 7957ae97aaa0bc2530d209fe1247fa308cf0c93490dbb15ded5781f434bf132c | 23a4c72a0299e9ab2af725abaf399ead2493921ab1df5fa49643c4c5ff36720f | c1cc(NC2CCCCC2)ccn1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3]-[CH2;D2;+0:4]-[C:5]-[C:6].[O;H0;D1;+0:7]=[C;H0;D3;+0:8]1-[C:9]-[C:10]-[C:11](-[NH;D2;+0:12]-[c:13]2:[c:14]:[c:15]:[#7;a:16]:[c:17]:[c:18]:2)-[C:19]-[C:20]-1>>[C:6]-[C:5]-[C;H0;D4;+0:4](-[OH;D1;+0:7])(-[C:3]-[C:2]-[CH3;D1;+0:1])-[N;H0;D3;+0:12](-[C:11]1-[C:10]-[C:9]-[CH2;D2;+0:8]-[C:20]-[C:1... | null | [] | null | null | null | null | The Grignard solution is prepared from 0.73 g of magnesium and 6.0 g of octyl bromide in 50 ml of absolute THF. 2.8 g of 4-(4-oxocyclohexylamino)-3-methoxy-2-methylpyridine in 20 ml of THF are added dropwise to the solution. After 2 hours the mixture is acidified with 2N HCl. The THF is then distilled off in vacuo at r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Secondary amine | Tertiary alcohol.Tertiary amine | C1CCCCC1 | C1CCCCC1 | c1ccncc1.C1CCCCC1 | Br- | null | null | null | CCCCCCCCBr.COc1c(NC2CCC(=O)CC2)ccnc1C>>CCCCC(O)(CCC)N(c1ccnc(C)c1OC)C1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ed5d30e63cae482aa9ed8a44a63361f9 | CC(C)(C)c1ccc(N)cc1.COc1c(Cl)ccnc1C>>COc1c(Nc2ccc(C(C)(C)C)cc2)ccnc1C | ClC1=C(C(=NC=C1)C)OC.C(C)(C)(C)C1=CC=C(N)C=C1.[OH-].[Na+]>>C(C)(C)(C)C1=CC=C(NC2=C(C(=NC=C2)C)OC)C=C1 | [NH2:5][c:6]1[cH:7][cH:8][c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[cH:14][cH:15]1.Cl[c:4]1[c:3]([O:2][CH3:1])[c:19]([CH3:20])[n:18][cH:17][cH:16]1>>[CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[cH:14][cH:15]2)[cH:16][cH:17][n:18][c:19]1[CH3:20] | CC(C)(C)c1ccc(N)cc1.COc1c(Cl)ccnc1C | COc1c(Nc2ccc(C(C)(C)C)cc2)ccnc1C | null | null | C1(=CC=CC=C1)O | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2ccncc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C;D1;H3:6]):[c:7]:1-[#8:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12]>>[#8:8]-[c:7]1:[c:5](-[C;D1;H3:6]):[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | 7.9 g of 4-chloro-3-methoxy-2-methylpyridine and 22.4 g of 4-tert-butylaniline are heated at 120° C. for 8 hours in 20 g of phenol. After cooling, the mixture is poured into NaOH and the product is extracted using methylene chloride. After concentrating, the excess of amine is distilled off in vacuo and the residue is ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | C1(=CC=CC=C1)O | null | null | CC(C)(C)c1ccc(N)cc1.COc1c(Cl)ccnc1C>C1(=CC=CC=C1)O>COc1c(Nc2ccc(C(C)(C)C)cc2)ccnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-61a0177588e440db829d21a8578b91c1 | COc1c(Nc2ccc(C(C)(C)C)cc2)ccnc1C>>COc1c(NC2CCC(C(C)(C)C)CC2)ccnc1C | C(C)(C)(C)C1=CC=C(NC2=C(C(=NC=C2)C)OC)C=C1>>C(C)(C)(C)C1CCC(CC1)NC1=C(C(=NC=C1)C)OC | [CH3:1][O:2][c:3]1[c:4]([NH:5][c:6]2[cH:7][cH:8][c:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[cH:14][cH:15]2)[cH:16][cH:17][n:18][c:19]1[CH3:20]>>[CH3:1][O:2][c:3]1[c:4]([NH:5][CH:6]2[CH2:7][CH2:8][CH:9]([C:10]([CH3:11])([CH3:12])[CH3:13])[CH2:14][CH2:15]2)[cH:16][cH:17][n:18][c:19]1[CH3:20] | COc1c(Nc2ccc(C(C)(C)C)cc2)ccnc1C | COc1c(NC2CCC(C(C)(C)C)CC2)ccnc1C | null | null | Cl.CO.O | Reduction | Arene hydrogenation | cfd1f3b98f7cd3ca3735c14f302dc0acdc6f0d4501cd6920cbb5c1a3d892ff3a | 312e9350dcad67590617294c0eb017edf0b9fbfe6133c06a3f393b871a889092 | c1cc(NC2CCCCC2)ccn1 | [C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[c;H0;D3;+0:5]1:[cH;D2;+0:6]:[cH;D2;+0:7]:[c;H0;D3;+0:8](-[#7:9]-[c:10]):[cH;D2;+0:11]:[cH;D2;+0:12]:1>>[C;D1;H3:1]-[C:2](-[C;D1;H3:3])(-[C;D1;H3:4])-[CH;D3;+0:5]1-[CH2;D2;+0:6]-[CH2;D2;+0:7]-[CH;D3;+0:8](-[#7:9]-[c:10])-[CH2;D2;+0:11]-[CH2;D2;+0:12]-1 | null | [] | null | null | null | null | 1 g of 4-(4-tert-butylanilino)-3-methoxy-2-methylpyridine in 20 ml of methanol, 3.7 ml of 2N HCl and 1.3 ml of water are hydrogenated at room temperature and normal pressure until absorption of hydrogen has ended using 1 g of rhodium on alumina (5% strength). After filtering and concentrating 1 g of syrup remains=100% ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | c1ccccc1 | C1CCCCC1 | c1ccncc1.C1CCCCC1 | null | Cl.CO.O | null | null | COc1c(Nc2ccc(C(C)(C)C)cc2)ccnc1C>Cl.CO.O>COc1c(NC2CCC(C(C)(C)C)CC2)ccnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d4704ef73c974a1ead59af967133bf07 | CCOCCOCCOc1ccc(C2CCC(N)CC2)cc1.Cc1nccc(Cl)c1Cl>>CCOCCOCCOc1ccc(C2CCC(Nc3ccnc(C)c3Cl)CC2)cc1 | ClC=1C(=NC=CC1Cl)C.C(COCCOCC)OC1=CC=C(C=C1)C1CCC(CC1)N>>C(COCCOCC)OC1=CC=C(C=C1)C1CCC(CC1)NC1=C(C(=NC=C1)C)Cl | [CH3:1][CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([CH:14]2[CH2:15][CH2:16][CH:17]([NH2:18])[CH2:27][CH2:28]2)[cH:29][cH:30]1.Cl[c:19]1[cH:20][cH:21][n:22][c:23]([CH3:24])[c:25]1[Cl:26]>>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][c:10]1[cH:11][cH:12][c:13]([CH:14]2[CH2:1... | CCOCCOCCOc1ccc(C2CCC(N)CC2)cc1.Cc1nccc(Cl)c1Cl | CCOCCOCCOc1ccc(C2CCC(Nc3ccnc(C)c3Cl)CC2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(C2CCC(Nc3ccncc3)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C;D1;H3:6]):[c:7]:1-[Cl;D1;H0:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12]>>[C:9]-[C:10](-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C;D1;H3:6]):[c:7]:1-[Cl;D1;H0:8])-[C:12] | 28 | [{"value": 28.0, "product": "C(COCCOCC)OC1=CC=C(C=C1)C1CCC(CC1)NC1=C(C(=NC=C1)C)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 4.5 | HOUR | Preparation was carried out analogously to Example 35 from 3,4-dichloro-2-methylpyridine and 4-(4-(3,6-dioxaoctyloxy)phenyl)cyclohexylamine. After 4.5 hours the mixture is worked up. Yield: 28%
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccccc1.C1CCCCC1.c1ccncc1 | HCl | null | null | 4.5 | CCOCCOCCOc1ccc(C2CCC(N)CC2)cc1.Cc1nccc(Cl)c1Cl>>CCOCCOCCOc1ccc(C2CCC(Nc3ccnc(C)c3Cl)CC2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-70baa8bcab424511a56acfca39fce88b | CCOc1c(NC2CCC(=O)CC2)ccnc1C.c1ccc([P+](CCCC2CCCCC2)(c2ccccc2)c2ccccc2)cc1>>CCOc1c(NC2CCC(=CCCC3CCCCC3)CC2)ccnc1C | O=C1CCC(CC1)NC1=C(C(=NC=C1)C)OCC.[Cl-].C1(CCCCC1)CCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C1(CCCCC1)CCC=C1CCC(CC1)NC1=C(C(=NC=C1)C)OCC | O=[C:10]1[CH2:9][CH2:8][CH:7]([NH:6][c:5]2[c:4]([O:3][CH2:2][CH3:1])[c:25]([CH3:26])[n:24][cH:23][cH:22]2)[CH2:21][CH2:20]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:11][CH2:12][CH2:13][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)cc1>>[CH3:1][CH2:2][O:3][c:4]1[c:5]([NH:6][CH:7]2[CH2:8][CH2:9][C:10](=[CH:11][CH2:12][CH2:1... | CCOc1c(NC2CCC(=O)CC2)ccnc1C.c1ccc([P+](CCCC2CCCCC2)(c2ccccc2)c2ccccc2)cc1 | CCOc1c(NC2CCC(=CCCC3CCCCC3)CC2)ccnc1C | null | null | null | C-C Coupling | Wittig with Phosphonium | 4ace91bfe286d7308b684482c14d0e07094c3e16f8d78c7715341add0f69a6d3 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | C(CCC1CCCCC1)=C1CCC(Nc2ccncc2)CC1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[C:6]-[C:7]-[CH2;D2;+0:8]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:6]-[C:7]-[CH;D2;+0:8]=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5] | 42 | [{"value": 42.0, "product": "C1(CCCCC1)CCC=C1CCC(CC1)NC1=C(C(=NC=C1)C)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Preparation was carried out analogously to Example 27 from 4-(4-oxocyclohexylamino)-3-ethoxy-2-methylpyridine and 3-cyclohexylpropyltriphenylphosphonium chloride. Yield: 42%
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1CCCCC1.c1ccccc1.c1ccccc1.c1ccccc1 | C1CCCCC1 | c1ccncc1.C1CCCCC1.C1CCCCC1 | HO- | null | null | null | CCOc1c(NC2CCC(=O)CC2)ccnc1C.c1ccc([P+](CCCC2CCCCC2)(c2ccccc2)c2ccccc2)cc1>>CCOc1c(NC2CCC(=CCCC3CCCCC3)CC2)ccnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c2314524348047c3a3f43e522da4e6a5 | CCCCCCCCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.CCOc1c(NC2CCC(=O)CC2)ccnc1C>>CCCCCCCCCCC=C1CCC(Nc2ccnc(C)c2OCC)CC1 | O=C1CCC(CC1)NC1=C(C(=NC=C1)C)OCC.[Br-].C(CCCCCCCCCC)[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(CCCCCCCCCC)=C1CCC(CC1)NC1=C(C(=NC=C1)C)OCC | c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])cc1.O=[C:12]1[CH2:13][CH2:14][CH:15]([NH:16][c:17]2[cH:18][cH:19][n:20][c:21]([CH3:22])[c:23]2[O:24][CH2:25][CH3:26])[CH2:27][CH2:28]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH... | CCCCCCCCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.CCOc1c(NC2CCC(=O)CC2)ccnc1C | CCCCCCCCCCC=C1CCC(Nc2ccnc(C)c2OCC)CC1 | null | null | null | C-C Coupling | Wittig with Phosphonium | 4ace91bfe286d7308b684482c14d0e07094c3e16f8d78c7715341add0f69a6d3 | 06a42e352cf517302d592bf38a2fd11b220014e39071074dc7becb6ee0bee4b2 | [CH]=C1CCC(Nc2ccncc2)CC1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[C:6]-[C:7]-[CH2;D2;+0:8]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:3]-[C:2]-[C;H0;D3;+0:1](=[CH;D2;+0:8]-[C:7]-[C:6])-[C:4]-[C:5] | 51 | [{"value": 51.0, "product": "C(CCCCCCCCCC)=C1CCC(CC1)NC1=C(C(=NC=C1)C)OCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Preparation was carried out analogously to Example 27 from 4-(4-oxocyclohexylamino)-3-ethoxy-2-methylpyridine and undecyl triphenylphosphonium bromide. Yield: 51%
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | c1ccccc1.c1ccccc1.c1ccccc1.C1CCCCC1 | C1CCCCC1 | C1CCCCC1.c1ccncc1 | HO- | null | null | null | CCCCCCCCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.CCOc1c(NC2CCC(=O)CC2)ccnc1C>>CCCCCCCCCCC=C1CCC(Nc2ccnc(C)c2OCC)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-23dc3d980fa24e5c82e553d717c3da9c | CC1(C)COC2(CCC(O)CC2)OC1.COc1c(Cl)ccnc1C>>COc1c(OC2CCC3(CC2)OCC(C)(C)CO3)ccnc1C | ClC1=C(C(=NC=C1)C)OC.CC1(COC2(OC1)CCC(CC2)O)C>>CC1(COC2(OC1)CCC(CC2)OC2=C(C(=NC=C2)C)OC)C | [OH:5][CH:6]1[CH2:7][CH2:8][C:9]2([CH2:10][CH2:11]1)[O:12][CH2:13][C:14]([CH3:15])([CH3:16])[CH2:17][O:18]2.Cl[c:4]1[c:3]([O:2][CH3:1])[c:22]([CH3:23])[n:21][cH:20][cH:19]1>>[CH3:1][O:2][c:3]1[c:4]([O:5][CH:6]2[CH2:7][CH2:8][C:9]3([CH2:10][CH2:11]2)[O:12][CH2:13][C:14]([CH3:15])([CH3:16])[CH2:17][O:18]3)[cH:19][cH:20][... | CC1(C)COC2(CCC(O)CC2)OC1.COc1c(Cl)ccnc1C | COc1c(OC2CCC3(CC2)OCC(C)(C)CO3)ccnc1C | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | c5d1a3b8ff2abf1a13e793598317fd14bafd4f883bb7758ba14c5a0a08360b3f | 1f70dbbaebc288b3a5d3f37803812d9d22b151831cd4b8351080508554b19875 | c1cc(OC2CCC3(CC2)OCCCO3)ccn1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C;D1;H3:6]):[c:7]:1-[#8:8].[C:9]-[C:10](-[OH;D1;+0:11])-[C:12]>>[#8:8]-[c:7]1:[c:5](-[C;D1;H3:6]):[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:11]-[C:10](-[C:9])-[C:12] | 75 | [{"value": 75.0, "product": "CC1(COC2(OC1)CCC(CC2)OC2=C(C(=NC=C2)C)OC)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Preparation was carried out analogously to Example 43 from 4-chloro-3-methoxy-2-methylpyridine and 3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-ol. Yield: 75%; M.p.: 90° C.
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Secondary alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CCC2(CC1)OCCCO2 | HCl | null | null | null | CC1(C)COC2(CCC(O)CC2)OC1.COc1c(Cl)ccnc1C>>COc1c(OC2CCC3(CC2)OCC(C)(C)CO3)ccnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-91ac38e1cd644fcdbb0f2037b7004087 | COc1c(OC2CCC3(CC2)OCC(C)(C)CO3)ccnc1C>>COc1c(OC2CCC(=O)CC2)ccnc1C | CC1(COC2(OC1)CCC(CC2)OC2=C(C(=NC=C2)C)OC)C.C(=O)O>>O=C1CCC(CC1)OC1=C(C(=NC=C1)C)OC | CC1(C)CO[C:9]2([CH2:8][CH2:7][CH:6]([O:5][c:4]3[c:3]([O:2][CH3:1])[c:16]([CH3:17])[n:15][cH:14][cH:13]3)[CH2:12][CH2:11]2)[O:10]C1>>[CH3:1][O:2][c:3]1[c:4]([O:5][CH:6]2[CH2:7][CH2:8][C:9](=[O:10])[CH2:11][CH2:12]2)[cH:13][cH:14][n:15][c:16]1[CH3:17] | COc1c(OC2CCC3(CC2)OCC(C)(C)CO3)ccnc1C | COc1c(OC2CCC(=O)CC2)ccnc1C | null | null | CC(=O)C | Miscellaneous | Ketal hydrolysis to ketone | fbb0a69919ca8d69f9c509c0c507f9428ad325b527d1b7c038667a6ade8ddaf4 | 547697208447432e865290cf95eed8e4fcddc12f59856b7ddbf24dc1accb1210 | O=C1CCC(Oc2ccncc2)CC1 | C-C1(-C)-C-O-[C;H0;D4;+0:1](-[C:2]-[C:3])(-[C:4]-[C:5])-[O;H0;D2;+0:6]-C-1>>[C:3]-[C:2]-[C;H0;D3;+0:1](=[O;H0;D1;+0:6])-[C:4]-[C:5] | null | [] | null | null | null | null | 1 g of 4-(3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-9-yloxy)-3-methoxy-2-methylpyridine is stirred with 20 ml of formic acid and 5 ml of acetone for 5 hours. The residue which remains after concentrating is purified by chromatography on silica gel using ethyl acetate. 0.3 g=41%; m.p.: 56° to 57° C.
Conditions: See reacti... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Ketone | C1CCC2(CC1)OCCCO2 | C1CCCCC1 | c1ccncc1.C1CCCCC1 | HO- | CC(=O)C | null | null | COc1c(OC2CCC3(CC2)OCC(C)(C)CO3)ccnc1C>CC(=O)C>COc1c(OC2CCC(=O)CC2)ccnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-81b10c28bd9c47d5984b354d59da9d19 | CC(C)(C)c1ccc(OCCO)cc1.COc1c(Cl)ccnc1C>>COc1c(OCCOc2ccc(C(C)(C)C)cc2)ccnc1C | [Cl-].[NH4+].[H-].[Na+].CC1=NC=CC(=C1OC)Cl.C(C)(C)(C)C1=CC=C(OCCO)C=C1>>CC1=NC=CC(=C1OC)OCCOC1=CC=C(C=C1)C(C)(C)C | [OH:5][CH2:6][CH2:7][O:8][c:9]1[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]1.Cl[c:4]1[c:3]([O:2][CH3:1])[c:22]([CH3:23])[n:21][cH:20][cH:19]1>>[CH3:1][O:2][c:3]1[c:4]([O:5][CH2:6][CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[cH:17][cH:18]2)[cH:19][cH:20][n:21][c:22... | CC(C)(C)c1ccc(OCCO)cc1.COc1c(Cl)ccnc1C | COc1c(OCCOc2ccc(C(C)(C)C)cc2)ccnc1C | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | ea617b323b892eda23f5ae30e789991ea9692064ef355a16e8ed81c16e743d2b | a4cafa7bcd156e21cca6eaac1b32e28ec8540642a31181122e6957f3d7559631 | c1ccc(OCCOc2ccncc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C;D1;H3:6]):[c:7]:1-[#8:8].[C:9]-[C:10]-[OH;D1;+0:11]>>[#8:8]-[c:7]1:[c:5](-[C;D1;H3:6]):[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[O;H0;D2;+0:11]-[C:10]-[C:9] | null | [] | 60 | CELSIUS | 5 | HOUR | A mixture of 1.57 g (10 mmol) of 2-methyl-3-methoxy-4-chloropyridine, 2.52 g (13 mmol) of 2-(4-tert-butylphenoxy)ethanol and 15 ml of DMSO is added dropwise at 25° C. to 0.36 g (12 mmol) of NaH (80% strength) in 25 ml of DMSO. The mixture is then stirred at 60° C. for 5 hours. For working up, saturated ammonium chlorid... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary alcohol | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | CS(=O)C | 60 | 5 | CC(C)(C)c1ccc(OCCO)cc1.COc1c(Cl)ccnc1C>CS(=O)C>COc1c(OCCOc2ccc(C(C)(C)C)cc2)ccnc1C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cf5b984642ac4823a3cc135bcd09ba2e | CCc1nccc(Cl)c1Cl.NOCc1ccccc1>>CCc1nccc(NOCc2ccccc2)c1Cl | ClC=1C(=NC=CC1Cl)CC.C(C1=CC=CC=C1)ON>>C(C1=CC=CC=C1)ONC1=C(C(=NC=C1)CC)Cl | Cl[c:7]1[cH:6][cH:5][n:4][c:3]([CH2:2][CH3:1])[c:17]1[Cl:18].[NH2:8][O:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1>>[CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][c:7]([NH:8][O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:17]1[Cl:18] | CCc1nccc(Cl)c1Cl.NOCc1ccccc1 | CCc1nccc(NOCc2ccccc2)c1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CONc2ccncc2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C:6]):[c:7]:1-[Cl;D1;H0:8].[C:9]-[#8:10]-[NH2;D1;+0:11]>>[C:9]-[#8:10]-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C:6]):[c:7]:1-[Cl;D1;H0:8] | 99 | [{"value": 99.0, "product": "C(C1=CC=CC=C1)ONC1=C(C(=NC=C1)CC)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Preparation was carried out analogously to Example 1 from 3,4-dichloro-2-ethylpyridine and O-benzylhydroxylamine. Yield: 99%
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1ccccc1 | HCl | null | null | null | CCc1nccc(Cl)c1Cl.NOCc1ccccc1>>CCc1nccc(NOCc2ccccc2)c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aef921fb8b7c405c92fb8244dd4e6640 | CCc1nccc(NOCc2ccccc2)c1Cl.Cc1ccc(S(=O)(=O)OC2CCC3(CCCCC3)CC2)cc1>>CCc1nccc(N(OCc2ccccc2)C2CCC3(CCCCC3)CC2)c1Cl | C(C1=CC=CC=C1)ONC1=C(C(=NC=C1)CC)Cl.S(=O)(=O)(C1=CC=C(C)C=C1)OC1CCC2(CC1)CCCCC2>>C(C1=CC=CC=C1)ON(C1CCC2(CC1)CCCCC2)C2=C(C(=NC=C2)CC)Cl | [CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][c:7]([NH:8][O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[c:28]1[Cl:29].Cc1ccc(S(=O)(=O)O[CH:17]2[CH2:18][CH2:19][C:20]3([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[CH2:26][CH2:27]2)cc1>>[CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][c:7]([N:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][c... | CCc1nccc(NOCc2ccccc2)c1Cl.Cc1ccc(S(=O)(=O)OC2CCC3(CCCCC3)CC2)cc1 | CCc1nccc(N(OCc2ccccc2)C2CCC3(CCCCC3)CC2)c1Cl | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | af1756b5677c92e5b4e2341e6093e94973e66aa0b38d806e82c3b1d18d6f34c3 | 71b4ac4449ece5e0df64e56caf0f1cbac76e83f802a92104cfb6c6c861b6a71c | c1ccc(CON(c2ccncc2)C2CCC3(CCCCC3)CC2)cc1 | C-c1:c:c:c(-S(=O)(=O)-O-[CH;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5]):c:c:1.[C:6]-[#8:7]-[NH;D2;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[C:6]-[#8:7]-[N;H0;D3;+0:8](-[CH;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5])-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1 | 95 | [{"value": 95.0, "product": "C(C1=CC=CC=C1)ON(C1CCC2(CC1)CCCCC2)C2=C(C(=NC=C2)CC)Cl", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Was prepared analogously to Example 7 from 4-(O-benzylhydroxylamino)-3-chloro-2-ethylpyridine (Example 52) and 3-tosyloxyspiro[5.5]undecane. Yield: 95%
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Secondary amine | Tertiary amine | c1ccccc1.C1CCC2(CC1)CCCCC2 | C1CCC2(CC1)CCCCC2 | c1ccncc1.c1ccccc1.C1CCC2(CC1)CCCCC2 | TsOH.HO- | null | null | null | CCc1nccc(NOCc2ccccc2)c1Cl.Cc1ccc(S(=O)(=O)OC2CCC3(CCCCC3)CC2)cc1>>CCc1nccc(N(OCc2ccccc2)C2CCC3(CCCCC3)CC2)c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c0062b7363ec4154b00b2b22681d2f1d | CCc1nccc(Cl)c1Cl.NC1CCC(=Cc2ccc(Cl)cc2Cl)CC1>>CCc1nccc(NC2CCC(=Cc3ccc(Cl)cc3Cl)CC2)c1Cl | C([O-])(O)=O.[Na+].ClC=1C(=NC=CC1Cl)CC.ClC1=C(C=C2CCC(CC2)N)C=CC(=C1)Cl.[Cl-].[NH4+]>>ClC=1C(=NC=CC1NC1CCC(CC1)=CC1=C(C=C(C=C1)Cl)Cl)CC | Cl[c:7]1[cH:6][cH:5][n:4][c:3]([CH2:2][CH3:1])[c:24]1[Cl:25].[NH2:8][CH:9]1[CH2:10][CH2:11][C:12](=[CH:13][c:14]2[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]2[Cl:21])[CH2:22][CH2:23]1>>[CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][c:7]([NH:8][CH:9]2[CH2:10][CH2:11][C:12](=[CH:13][c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]3... | CCc1nccc(Cl)c1Cl.NC1CCC(=Cc2ccc(Cl)cc2Cl)CC1 | CCc1nccc(NC2CCC(=Cc3ccc(Cl)cc3Cl)CC2)c1Cl | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | C(=C1CCC(Nc2ccncc2)CC1)c1ccccc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C:6]):[c:7]:1-[Cl;D1;H0:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12]>>[C:9]-[C:10](-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C:6]):[c:7]:1-[Cl;D1;H0:8])-[C:12] | 7 | [{"value": 7.0, "product": "ClC=1C(=NC=CC1NC1CCC(CC1)=CC1=C(C=C(C=C1)Cl)Cl)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 1.6 g of 3,4-dichloro-2-ethylpyridine and 2.5 g of 4-(2,4-dichlorobenzylidene)cyclohexylamine are heated at 180° C. for 3.5 hours together with 55 g of ammonium chloride in 9 ml of N-methylpyrrolidone. After cooling, the mixture is poured into saturated sodium bicarbonate solution and extracted with ethyl acetate. The ... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CCCCC1.c1ccccc1 | HCl | CN1C(CCC1)=O | null | null | CCc1nccc(Cl)c1Cl.NC1CCC(=Cc2ccc(Cl)cc2Cl)CC1>CN1C(CCC1)=O>CCc1nccc(NC2CCC(=Cc3ccc(Cl)cc3Cl)CC2)c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-604b730a698f47929475fa327db8b570 | CCc1nccc(Cl)c1Cl.COCCOc1ccc(C2CCC(N)CC2)cc1>>CCc1nccc(NC2CCC(c3ccc(OCCOC)cc3)CC2)c1Cl | ClC=1C(=NC=CC1Cl)CC.COCCOC1=CC=C(C=C1)C1CCC(CC1)N>>ClC=1C(=NC=CC1NC1CCC(CC1)C1=CC=C(C=C1)OCCOC)CC | Cl[c:7]1[cH:6][cH:5][n:4][c:3]([CH2:2][CH3:1])[c:26]1[Cl:27].[NH2:8][CH:9]1[CH2:10][CH2:11][CH:12]([c:13]2[cH:14][cH:15][c:16]([O:17][CH2:18][CH2:19][O:20][CH3:21])[cH:22][cH:23]2)[CH2:24][CH2:25]1>>[CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][c:7]([NH:8][CH:9]2[CH2:10][CH2:11][CH:12]([c:13]3[cH:14][cH:15][c:16]([O:17][CH2:18... | CCc1nccc(Cl)c1Cl.COCCOc1ccc(C2CCC(N)CC2)cc1 | CCc1nccc(NC2CCC(c3ccc(OCCOC)cc3)CC2)c1Cl | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(C2CCC(Nc3ccncc3)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C:6]):[c:7]:1-[Cl;D1;H0:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12]>>[C:9]-[C:10](-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C:6]):[c:7]:1-[Cl;D1;H0:8])-[C:12] | 11 | [{"value": 11.0, "product": "ClC=1C(=NC=CC1NC1CCC(CC1)C1=CC=C(C=C1)OCCOC)CC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Preparation took place analogously to Example 59 from 3,4-dichloro-2-ethylpyridine and 4-(4-(2-methoxyethoxy)phenyl)cyclohexylamine. Yield: 11% (cis/trans mixture)
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CCCCC1.c1ccccc1 | HCl | null | null | null | CCc1nccc(Cl)c1Cl.COCCOc1ccc(C2CCC(N)CC2)cc1>>CCc1nccc(NC2CCC(c3ccc(OCCOC)cc3)CC2)c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4b4a7f0be88e4110be087990ba37caf4 | CC(C)CCC1CCC(N)C1.Cc1nccc(Cl)c1Cl>>Cc1nccc(NC2CCC(CCC(C)C)C2)c1Cl | ClC=1C(=NC=CC1Cl)C.C(CC(C)C)C1CC(CC1)N>>ClC=1C(=NC=CC1NC1CC(CC1)CCC(C)C)C | [NH2:7][CH:8]1[CH2:9][CH2:10][CH:11]([CH2:12][CH2:13][CH:14]([CH3:15])[CH3:16])[CH2:17]1.Cl[c:6]1[cH:5][cH:4][n:3][c:2]([CH3:1])[c:18]1[Cl:19]>>[CH3:1][c:2]1[n:3][cH:4][cH:5][c:6]([NH:7][CH:8]2[CH2:9][CH2:10][CH:11]([CH2:12][CH2:13][CH:14]([CH3:15])[CH3:16])[CH2:17]2)[c:18]1[Cl:19] | CC(C)CCC1CCC(N)C1.Cc1nccc(Cl)c1Cl | Cc1nccc(NC2CCC(CCC(C)C)C2)c1Cl | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1cc(NC2CCCC2)ccn1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C;D1;H3:6]):[c:7]:1-[Cl;D1;H0:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12]>>[C:9]-[C:10](-[NH;D2;+0:11]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[C;D1;H3:6]):[c:7]:1-[Cl;D1;H0:8])-[C:12] | 61 | [{"value": 61.0, "product": "ClC=1C(=NC=CC1NC1CC(CC1)CCC(C)C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Preparation was carried out as in Example 59 from 3,4-dichloro-2-methylpyridine and 3-isoamylcyclopentylamine. Yield: 61%
Conditions: See reaction.notes.procedure_details.
Workup: Preparation | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CCCC1 | HCl | null | null | null | CC(C)CCC1CCC(N)C1.Cc1nccc(Cl)c1Cl>>Cc1nccc(NC2CCC(CCC(C)C)C2)c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5d3b4c5598fc43c8868c332153f62858 | CCc1nccc(N)c1Br.O=C1CCC(c2ccccc2)CC1>>CCc1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Br | ClC(C)Cl.C(C)(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+].C(C)(=O)O.C(O)([O-])=O.[Na+].C1(=CC=CC=C1)C1CCC(CC1)=O.C(OCC)(OCC)OCC.C(C)C1=NC=CC(=C1Br)N>>C(C)C1=NC=CC(=C1Br)N[C@@H]1CC[C@@H](CC1)C1=CC=CC=C1 | [CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][c:7]([NH2:8])[c:21]1[Br:22].O=[C:9]1[CH2:10][CH2:11][CH:12]([c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][CH2:20]1>>[CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][c:7]([NH:8][C@H:9]2[CH2:10][CH2:11][C@@H:12]([c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[CH2:19][CH2:20]2)[c:21]1[Br:22] | CCc1nccc(N)c1Br.O=C1CCC(c2ccccc2)CC1 | CCc1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Br | null | B(F)(F)F.CCOCC | C(C)O | Heteroatom Alkylation and Arylation | Reductive amination with ketone | b3c233679044776f397868647ebe4ff6248540afeba9e0b29baba9f61657514b | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc([C@H]2CC[C@@H](Nc3ccncc3)CC2)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[NH2;D1;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1>>[C:3]-[C:2]-[C@@H;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1)-[C:4]-[C:5] | null | [] | 50 | CELSIUS | null | null | 3.48 g (20 mmol) of 4-phenylcyclohexanone in 3.3 ml of ethanol are treated with 3.3 ml of triethyl orthoformate and 2 drops of boron trifluoride etherate and warmed at 50° C. for 30 min. After addition of 2.01 g (10mmol) of 2-ethyl-3-bromo-4-aminopyridine the reaction mixture is heated at 135°-140° C. for 3.5-4 hours w... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CCCCC1 | C1CCCCC1 | c1ccncc1.C1CCCCC1.c1ccccc1 | Other | B(F)(F)F.CCOCC.C(C)O | 50 | null | CCc1nccc(N)c1Br.O=C1CCC(c2ccccc2)CC1>B(F)(F)F.CCOCC.C(C)O>CCc1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bbef73e40290461c80e983d0e34bab95 | CC(C)(C)CC(C)(C)C1CCC(=O)CC1.CCC1(N)CC=NC=C1Br>>CCc1cc(N[C@H]2CC[C@@H](C(C)(C)CC(C)(C)C)CC2)c(Br)cn1 | C(C)C1(CC=NC=C1Br)N.CC(CC(C)(C)C)(C)C1CCC(CC1)=O.C(C)(C)OC(C)C>>C(C)C1=NC=C(C(=C1)N[C@@H]1CC[C@@H](CC1)C(CC(C)(C)C)(C)C)Br | O=[C:7]1[CH2:8][CH2:9][CH:10]([C:11]([CH3:12])([CH3:13])[CH2:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH2:19][CH2:20]1.[CH3:1][CH2:2][C:5]1([NH2:6])[CH2:4][CH:3]=[N:24][CH:23]=[C:21]1[Br:22]>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]([NH:6][C@H:7]2[CH2:8][CH2:9][C@@H:10]([C:11]([CH3:12])([CH3:13])[CH2:14][C:15]([CH3:16])([CH3:17])... | CC(C)(C)CC(C)(C)C1CCC(=O)CC1.CCC1(N)CC=NC=C1Br | CCc1cc(N[C@H]2CC[C@@H](C(C)(C)CC(C)(C)C)CC2)c(Br)cn1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | bc051defa99e0c8466ed18b0d0ad954b653ef6cd7340cdb267907349f5057d04 | ee2865f0d3d0aaa7597f38906c8dd369eb866b8d7283f52b5a1f9674bce5f714 | c1cc(NC2CCCCC2)ccn1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[Br;D1;H0:6]-[C;H0;D3;+0:7]1=[CH;D2;+0:8]-[N;H0;D2;+0:9]=[CH;D2;+0:10]-[CH2;D2;+0:11]-[C;H0;D4;+0:12]-1(-[NH2;D1;+0:13])-[CH2;D2;+0:14]-[C;D1;H3:15]>>[Br;D1;H0:6]-[c;H0;D3;+0:7]1:[cH;D2;+0:8]:[n;H0;D2;+0:9]:[c;H0;D3;+0:10](-[CH2;D2;+0:14]-[C;D1;H3:15]):[cH;D2;+0:11]:[c;H0;D3;+... | null | [] | null | null | null | null | As Example 75, but using 2.01 g (10 mmol) of 4-ethyl-4-amino-5-bromopyridine instead of 2-ethyl-3-bromo-4-aminopyridine and 4.2 g (20 mmol) of 4-(1,1,3,3-tetramethylbutyl)cyclohexanone instead of 4-phenylcyclohexanone. Yield: 1.9 g (48%); Rf =0.39 (diisopropyl ether)
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Ketone.Substituted imine.Primary amine | Aromatic halide.Secondary amine | C1CCCCC1.C1=CN=CCC1 | c1ccncc1.C1CCCCC1 | c1ccncc1.C1CCCCC1 | HO- | null | null | null | CC(C)(C)CC(C)(C)C1CCC(=O)CC1.CCC1(N)CC=NC=C1Br>>CCc1cc(N[C@H]2CC[C@@H](C(C)(C)CC(C)(C)C)CC2)c(Br)cn1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-54a1898a2ac34fa5a7bd7f2b4fc5d5b1 | CC(C)(C)CC(C)(C)C1CCC(=O)CC1.COc1nccc(N)c1OC>>COc1nccc(N[C@H]2CC[C@@H](C(C)(C)CC(C)(C)C)CC2)c1OC | COC1=NC=CC(=C1OC)N.CC(CC(C)(C)C)(C)C1CCC(CC1)=O>>COC1=NC=CC(=C1OC)N[C@@H]1CC[C@@H](CC1)C(CC(C)(C)C)(C)C | O=[C:9]1[CH2:10][CH2:11][CH:12]([C:13]([CH3:14])([CH3:15])[CH2:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:21][CH2:22]1.[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]([NH2:8])[c:23]1[O:24][CH3:25]>>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]([NH:8][C@H:9]2[CH2:10][CH2:11][C@@H:12]([C:13]([CH3:14])([CH3:15])[CH2:16][C:17]([CH3:18... | CC(C)(C)CC(C)(C)C1CCC(=O)CC1.COc1nccc(N)c1OC | COc1nccc(N[C@H]2CC[C@@H](C(C)(C)CC(C)(C)C)CC2)c1OC | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with ketone | b3c233679044776f397868647ebe4ff6248540afeba9e0b29baba9f61657514b | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1cc(NC2CCCCC2)ccn1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[NH2;D1;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1>>[C:3]-[C:2]-[C@@H;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1)-[C:4]-[C:5] | null | [] | null | null | null | null | As Example 75, but using 1.54 g (10 mmol) of 2,3-dimethoxy-4-aminopyridine instead of 2-ethyl-3-bromo-4-amino-pyridine and 4.2 g (20 mmol) of 4-(1,1,3,3-tetramethylbutyl)cyclohexanone instead of 4-phenylcyclohexanone.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CCCCC1 | C1CCCCC1 | c1ccncc1.C1CCCCC1 | Other | null | null | null | CC(C)(C)CC(C)(C)C1CCC(=O)CC1.COc1nccc(N)c1OC>>COc1nccc(N[C@H]2CC[C@@H](C(C)(C)CC(C)(C)C)CC2)c1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4950a24c3bb24e6eb853f7c03d0888b7 | CC(C)c1nccc(N)c1Cl.O=C1CCC(c2ccccc2)CC1>>CC(C)c1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Cl | NC1=C(C(=NC=C1)C(C)C)Cl.C1(=CC=CC=C1)C1CCC(CC1)=O>>ClC=1C(=NC=CC1N[C@@H]1CC[C@@H](CC1)C1=CC=CC=C1)C(C)C | [CH3:1][CH:2]([CH3:3])[c:4]1[n:5][cH:6][cH:7][c:8]([NH2:9])[c:22]1[Cl:23].O=[C:10]1[CH2:11][CH2:12][CH:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH2:20][CH2:21]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[n:5][cH:6][cH:7][c:8]([NH:9][C@H:10]2[CH2:11][CH2:12][C@@H:13]([c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[CH2:20][CH2:2... | CC(C)c1nccc(N)c1Cl.O=C1CCC(c2ccccc2)CC1 | CC(C)c1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Cl | null | null | null | Heteroatom Alkylation and Arylation | Reductive amination with ketone | b3c233679044776f397868647ebe4ff6248540afeba9e0b29baba9f61657514b | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | c1ccc([C@H]2CC[C@@H](Nc3ccncc3)CC2)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[NH2;D1;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1>>[C:3]-[C:2]-[C@@H;D3;+0:1](-[NH;D2;+0:6]-[c:7]1:[c:8]:[c:9]:[#7;a:10]:[c:11]:[c:12]:1)-[C:4]-[C:5] | 26.6 | [{"value": 26.6, "product": "ClC=1C(=NC=CC1N[C@@H]1CC[C@@H](CC1)C1=CC=CC=C1)C(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Was prepared analogously to Example 75 starting from 4-amino-3-chloro-2-isopropylpyridine and 4-phenylcyclohexanone. Yield: 26.6%
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CCCCC1 | C1CCCCC1 | c1ccncc1.C1CCCCC1.c1ccccc1 | Other | null | null | null | CC(C)c1nccc(N)c1Cl.O=C1CCC(c2ccccc2)CC1>>CC(C)c1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d3878873efe84db9b86c10bc3e0d832a | Clc1ccnc(Cl)c1Br.N[C@H]1CC[C@@H](c2ccccc2)CC1>>Clc1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Br | C(O)([O-])=O.[Na+].ClC1=NC=CC(=C1Br)Cl.C1(=CC=CC=C1)[C@H]1CC[C@H](CC1)N.[Cl-].[NH4+]>>ClC1=NC=CC(=C1Br)N[C@@H]1CC[C@@H](CC1)C1=CC=CC=C1 | Cl[c:6]1[cH:5][cH:4][n:3][c:2]([Cl:1])[c:20]1[Br:21].[NH2:7][C@H:8]1[CH2:9][CH2:10][C@@H:11]([c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[CH2:18][CH2:19]1>>[Cl:1][c:2]1[n:3][cH:4][cH:5][c:6]([NH:7][C@H:8]2[CH2:9][CH2:10][C@@H:11]([c:12]3[cH:13][cH:14][cH:15][cH:16][cH:17]3)[CH2:18][CH2:19]2)[c:20]1[Br:21] | Clc1ccnc(Cl)c1Br.N[C@H]1CC[C@@H](c2ccccc2)CC1 | Clc1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Br | null | null | CN1C(CCC1)=O | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c026a7bf7aba66b20cf21a13c528689aaaa1c05901524d62b36ca0c3b0572cef | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc([C@H]2CC[C@@H](Nc3ccncc3)CC2)cc1 | Cl-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[#7;a:4]:[c:5](-[Cl;D1;H0:6]):[c:7]:1-[Br;D1;H0:8].[C:9]-[C:10](-[NH2;D1;+0:11])-[C:12]>>[Br;D1;H0:8]-[c:7]1:[c:5](-[Cl;D1;H0:6]):[#7;a:4]:[c:3]:[c:2]:[c;H0;D3;+0:1]:1-[NH;D2;+0:11]-[C:10](-[C:9])-[C:12] | null | [] | null | null | null | null | 2.27 g (10 mmol) of 2,4-dichloro-3-bromopyridine, 2.6 g (15 mmol) of cis-4-phenylcyclohexylamine and 0.1 g of ammonium chloride are heated at 120° C. for 10 hours in 10 ml of N-methylpyrrolidone. After cooling, saturated sodium hydrogencarbonate solution is added and the reaction product is extracted with ethyl acetate... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CCCCC1.c1ccccc1 | HCl | CN1C(CCC1)=O | null | null | Clc1ccnc(Cl)c1Br.N[C@H]1CC[C@@H](c2ccccc2)CC1>CN1C(CCC1)=O>Clc1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5a04f014ea6d40c2b125f6974f5951e3 | C[O-].Clc1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Br>>COc1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Br | Cl.ClC1=NC=CC(=C1Br)N[C@@H]1CC[C@@H](CC1)C1=CC=CC=C1.C[O-].[Na+].O>>COC1=NC=CC(=C1Br)N[C@@H]1CC[C@@H](CC1)C1=CC=CC=C1 | [CH3:1][O-:2].Cl[c:3]1[n:4][cH:5][cH:6][c:7]([NH:8][C@H:9]2[CH2:10][CH2:11][C@@H:12]([c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[CH2:19][CH2:20]2)[c:21]1[Br:22]>>[CH3:1][O:2][c:3]1[n:4][cH:5][cH:6][c:7]([NH:8][C@H:9]2[CH2:10][CH2:11][C@@H:12]([c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[CH2:19][CH2:20]2)[c:21]1[Br:22] | C[O-].Clc1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Br | COc1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Br | null | null | CN(C=O)C.CO | Heteroatom Alkylation and Arylation | OtherReaction | 600484490705932a09b3fac6538a42c6f3fc156ab44a4ea0bbd020dd3eafd6ff | 51fd03eb6a688046e417b9ed09ea0e72062396d005af1318b9b5f376a97da959 | c1ccc([C@H]2CC[C@@H](Nc3ccncc3)CC2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4](-[Br;D1;H0:5]):[c:6].[C;D1;H3:7]-[O-;H0;D1:8]>>[Br;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[O;H0;D2;+0:8]-[C;D1;H3:7]):[#7;a:2]:[c:3] | null | [] | 80 | CELSIUS | null | null | 2.21 g (6.04 mmol) of 2-chloro-3-bromo-4-(cis-4-phenylcyclohexylamino)pyridine in 30 ml of dimethylformamide are treated with 4.31 ml of 30% strength solution of sodium methoxide in methanol and the mixture is heated at 80° C. for 1 hour. After cooling, water is added, the mixture is adjusted to pH 8 using 1/2 conc. hy... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Ether | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CCCCC1.c1ccccc1 | Other | CN(C=O)C.CO | 80 | null | C[O-].Clc1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Br>CN(C=O)C.CO>COc1nccc(N[C@H]2CC[C@@H](c3ccccc3)CC2)c1Br |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-db32eb67f898496ca933619d4788c566 | CS(=O)(=O)OCC1CN(c2ccc(C#N)cc2)C(=O)O1>>N#Cc1ccc(NCC(O)CO)cc1 | O1C(CO)C1.[O-]C1=CC=CC=C1.C(#N)C1=CC=C(C=C1)N1C(OC(C1)COS(=O)(=O)C)=O.NC1=CC=C(C#N)C=C1>>OC(CNC1=CC=C(C#N)C=C1)CO | CS(=O)(=O)[O:12][CH2:11][CH:9]1[CH2:8][N:7]([c:6]2[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:14][cH:13]2)C(=O)[O:10]1>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][CH:9]([OH:10])[CH2:11][OH:12])[cH:13][cH:14]1 | CS(=O)(=O)OCC1CN(c2ccc(C#N)cc2)C(=O)O1 | N#Cc1ccc(NCC(O)CO)cc1 | null | null | CN(C=O)C | Functional Group Interconversion | OtherReaction | c894d305e402208599f7816fc6365e0abd5e0da113ee8f8951bfed6d3b392d45 | 66c3a775fc290b542b49287863ddd8d38d401ff60c247697e43dbe4d3514597a | c1ccccc1 | C-S(=O)(=O)-[O;H0;D2;+0:1]-[C:2]-[C:3]1-[C:4]-[N;H0;D3;+0:5](-[c:6](:[c:7]):[c:8])-C(=O)-[O;H0;D2;+0:9]-1>>[OH;D1;+0:9]-[C:3](-[C:2]-[OH;D1;+0:1])-[C:4]-[NH;D2;+0:5]-[c:6](:[c:7]):[c:8] | null | [] | null | null | 30 | MINUTE | 1 Equivalent of NaH is added to a solution of 1.7 g of Na p-methoxycarbonylmethylphenoxide (obtainable by converting p-hydroxybenzyl cyanide into the corresponding carboxylic acid, esterifying with methanol to give p-methoxycarbonylmethylphenol and subsequently converting the latter into the phenoxide) in 20 ml of dime... | 10.6084/m9.figshare.5104873.v1 | null | Mesylate.Carbamic ester | Primary alcohol.Secondary alcohol.Secondary amine | C1COC[NH]1 | null | c1ccccc1 | MsOH | CN(C=O)C | null | 0.5 | CS(=O)(=O)OCC1CN(c2ccc(C#N)cc2)C(=O)O1>CN(C=O)C>N#Cc1ccc(NCC(O)CO)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b93694f35b514da089ea14094910a4e3 | COC(=O)Cc1ccc(OCC2CN(c3ccc(C#N)cc3)C(=O)O2)cc1>>COC(=O)Cc1ccc(OCC2CN(c3ccc(C(=N)N)cc3)C(=O)O2)cc1 | S.C(#N)C1=CC=C(C=C1)N1C(OC(C1)COC1=CC=C(C=C1)CC(=O)OC)=O.N1=CC=CC=C1>>C(N)(=N)C1=CC=C(C=C1)N1C(OC(C1)COC1=CC=C(C=C1)CC(=O)OC)=O | [CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH:12]2[CH2:13][N:14]([c:15]3[cH:16][cH:17][c:18]([C:19]#[N:20])[cH:22][cH:23]3)[C:24](=[O:25])[O:26]2)[cH:27][cH:28]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][c:9]([O:10][CH2:11][CH:12]2[CH2:13][N:14]([c:15]3[cH:16][cH:17][c:18]([C:19](=... | COC(=O)Cc1ccc(OCC2CN(c3ccc(C#N)cc3)C(=O)O2)cc1 | COC(=O)Cc1ccc(OCC2CN(c3ccc(C(=N)N)cc3)C(=O)O2)cc1 | null | null | C(C)N(CC)CC | Functional Group Addition | OtherReaction | b3aaef1538bea73aa85740ccbb089c1b6ca4b164a10fd32235acb6c78d1de6d9 | d1a81d2cc57b1a744f94f80261b8629cf532e8b73012860cc8db4db5903fee1a | O=C1OC(COc2ccccc2)CN1c1ccccc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[N;D1;H2:6]-[C;H0;D3;+0:2](=[NH;D1;+0:1])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 14 | HOUR | H2S gas is passed, at -10°, into a solution of 1.2 g of 3-p-cyanophenyl-5-(p-methoxycarbonyimethylphenoxymethyl)oxazolidin-2-one (obtainable in accordance with Example 1) in 50 ml of pyridine and 7 ml of triethylamine. The mixture is subsequently stirred at room temperature for 14 h and concentrated by evaporation; the... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccccc1.C1COC[NH]1.c1ccccc1 | Other | C(C)N(CC)CC | null | 14 | COC(=O)Cc1ccc(OCC2CN(c3ccc(C#N)cc3)C(=O)O2)cc1>C(C)N(CC)CC>COC(=O)Cc1ccc(OCC2CN(c3ccc(C(=N)N)cc3)C(=O)O2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-305f2a9859fc40c6bc0ea6b940f734ce | O=C(O)/C=C/C(=O)O>>O=C(O)/C=C/C(=O)O | ClC1=CC=C(C=C1)C=1C=C(C=NC1)C1N(CCC1)C.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.ClC1=CC=C(C=C1)C=1C=C(C=NC1)C1N(CCC1)C | [O:20]=[C:21]([OH:22])/[CH:23]=[CH:24]/[C:25](=[O:26])[OH:27]>>[O:20]=[C:21]([OH:22])/[CH:23]=[CH:24]/[C:25](=[O:26])[OH:27] | O=C(O)/C=C/C(=O)O | O=C(O)/C=C/C(=O)O | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 72 | [{"value": 72.0, "product": "C(\\C=C\\C(=O)O)(=O)O.ClC1=CC=C(C=C1)C=1C=C(C=NC1)C1N(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The above-referenced pyridine was converted into invention compound of Formula I by the addition of one equivalent of fumaric acid to a methanol (15 mL) solution of the free amine at 25° C. After 30 minutes the solvent was removed in vacuo and the residue pumped under high vacuum. Trituration with diethyl ether followe... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CO | null | null | O=C(O)/C=C/C(=O)O>CO>O=C(O)/C=C/C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-dae22e9fc1e04628a24bea85d2bbf97b | O=C(O)/C=C/C(=O)O>>O=C(O)/C=C/C(=O)O | FC1=CC=C(C=C1)C=1C=C(C=NC1)C1N(CCC1)C.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.FC1=CC=C(C=C1)C=1C=C(C=NC1)C1N(CCC1)C | [O:20]=[C:21]([OH:22])/[CH:23]=[CH:24]/[C:25](=[O:26])[OH:27]>>[O:20]=[C:21]([OH:22])/[CH:23]=[CH:24]/[C:25](=[O:26])[OH:27] | O=C(O)/C=C/C(=O)O | O=C(O)/C=C/C(=O)O | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 63 | [{"value": 63.0, "product": "C(\\C=C\\C(=O)O)(=O)O.FC1=CC=C(C=C1)C=1C=C(C=NC1)C1N(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The pyridine derivative described above was converted to a compound of the invention having Formula I by the addition of one equivalent of fumaric acid to a methanol (15 mL) solution of the free amine at 25° C. After 30 minutes the solvent was removed in vacuo and the residue pumped under high vacuum. Trituration with ... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CO | null | null | O=C(O)/C=C/C(=O)O>CO>O=C(O)/C=C/C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a5ca07eaa4874ceb97ba416d73a61749 | O=C(O)/C=C/C(=O)O>>O=C(O)/C=C/C(=O)O | O1C(=CC=C1)C=1C=C(C=NC1)C1N(CCC1)C.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.O1C(=CC=C1)C=1C=C(C=NC1)C1N(CCC1)C | [O:18]=[C:19]([OH:20])/[CH:21]=[CH:22]/[C:23](=[O:24])[OH:25]>>[O:18]=[C:19]([OH:20])/[CH:21]=[CH:22]/[C:23](=[O:24])[OH:25] | O=C(O)/C=C/C(=O)O | O=C(O)/C=C/C(=O)O | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 43 | [{"value": 43.0, "product": "C(\\C=C\\C(=O)O)(=O)O.O1C(=CC=C1)C=1C=C(C=NC1)C1N(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The above-described pyridine derivative was converted to invention compound of Formula I by the addition of one equivalent of fumaric acid to a methanol (15 mL) solution of the free amine at 25° C. After 30 minutes the solvent was removed in vacuo and the residue pumped under high vacuum. Trituration with diethyl ether... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CO | null | null | O=C(O)/C=C/C(=O)O>CO>O=C(O)/C=C/C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c2497e75ae4e46b1beb5da566107c8e5 | O=C(O)/C=C/C(=O)O>>O=C(O)/C=C/C(=O)O | C[Si](C=1C=C(C=NC1)C1N(CCC1)C)(C)C.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.C[Si](C=1C=C(C=NC1)C1N(CCC1)C)(C)C | [O:17]=[C:18]([OH:19])/[CH:20]=[CH:21]/[C:22](=[O:23])[OH:24]>>[O:17]=[C:18]([OH:19])/[CH:20]=[CH:21]/[C:22](=[O:23])[OH:24] | O=C(O)/C=C/C(=O)O | O=C(O)/C=C/C(=O)O | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 51 | [{"value": 51.0, "product": "C(\\C=C\\C(=O)O)(=O)O.C[Si](C=1C=C(C=NC1)C1N(CCC1)C)(C)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The above-described pyridine derivative was converted into invention compound of Formula I by the addition of one equivalent of fumaric acid to a methanol (5 mL) solution of the free amine at 25° C. After 30 minutes the solvent was removed in vacuo and the residue pumped under high vacuum. Trituration with diethyl ethe... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CO | null | null | O=C(O)/C=C/C(=O)O>CO>O=C(O)/C=C/C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-1f6771ce25094db9b1b82aab83d569ee | O=C(O)/C=C/C(=O)O>>O=C(O)/C=C/C(=O)O | C1(=CC=CC=C1)C#CC=1C=C(C=NC1)C1N(CCC1)C.C(\C=C\C(=O)O)(=O)O>>C(\C=C\C(=O)O)(=O)O.C1(=CC=CC=C1)C#CC=1C=C(C=NC1)C1N(CCC1)C | [O:21]=[C:22]([OH:23])/[CH:24]=[CH:25]/[C:26](=[O:27])[OH:28]>>[O:21]=[C:22]([OH:23])/[CH:24]=[CH:25]/[C:26](=[O:27])[OH:28] | O=C(O)/C=C/C(=O)O | O=C(O)/C=C/C(=O)O | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 56 | [{"value": 56.0, "product": "C(\\C=C\\C(=O)O)(=O)O.C1(=CC=CC=C1)C#CC=1C=C(C=NC1)C1N(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The above-described pyridine derivative was converted into invention compound of Formula I by the addition of one equivalent of fumaric acid to a methanol (10 mL) solution of the free amine at 25° C. After 30 minutes the solvent was removed in vacuo and the residue pumped under high vacuum. Trituration with diethyl eth... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CO | null | null | O=C(O)/C=C/C(=O)O>CO>O=C(O)/C=C/C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8f013d8744a5498fbfa2b609c4f93dd7 | CN1CCCC1c1cncc(C#C[Si](C)(C)C)c1>>C#Cc1cncc(C2CCCN2C)c1 | C[Si](C)(C)C#CC=1C=C(C=NC1)C1N(CCC1)C.C([O-])([O-])=O.[Cs+].[Cs+]>>C(#C)C=1C=C(C=NC1)C1N(CCC1)C | C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][n:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][N:12]2[CH3:13])[cH:14]1>>[CH:1]#[C:2][c:3]1[cH:4][n:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][N:12]2[CH3:13])[cH:14]1 | CN1CCCC1c1cncc(C#C[Si](C)(C)C)c1 | C#Cc1cncc(C2CCCN2C)c1 | null | null | CO | Deprotection | TMS deprotection from alkyne | e85676bb81da384790c9c858d44f182cdd01e3a79f77f7a239fe38487234cb96 | 56d526d7c9cb1bd7bee4940e216a9b1dd4597fd025a186b8d6e4675d8f4db26b | c1cncc(C2CCCN2)c1 | C-[Si](-C)(-C)-[C;H0;D2;+0:1]#[C:2]-[c:3]:[c:4]:[#7;a:5]>>[#7;a:5]:[c:4]:[c:3]-[C:2]#[CH;D1;+0:1] | null | [] | null | null | null | null | Repeating the procedure of Example 16, but using trimethylsilylacetylene in place of phenylacetylene, 5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine and the fumarate derivative thereof were obtained as follows. 5-Trimethylsilylethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine (516 mg, 2 mmol) and cesium carbonate (200 mg, 0.6... | 10.6084/m9.figshare.5104873.v1 | null | Alkyne.Silyl protective group | Alkyne | null | null | c1ccncc1.C1CC[NH]C1 | Other | CO | null | null | CN1CCCC1c1cncc(C#C[Si](C)(C)C)c1>CO>C#Cc1cncc(C2CCCN2C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d98a159036ee4b80b53a751599758e27 | CC(C)(C)[Si](C)(C)Cl.Oc1ccc(Br)cc1.c1c[nH]cn1>>CC(C)(C)[Si](C)(Cc1ccc(Br)cc1)O[Si](C)(Cc1ccc(Br)cc1)C(C)(C)C | O.BrC1=CC=C(C=C1)O.N1C=NC=C1.[Si](C)(C)(C(C)(C)C)Cl>>BrC1=CC=C(C=C1)C[Si](C)(C(C)(C)C)O[Si](C(C)(C)C)(C)CC1=CC=C(C=C1)Br | Cl[Si:5]([C:2]([CH3:3])([CH3:26])[CH3:29])([CH3:6])[CH3:7].[cH:9]1[cH:10][c:11]([Br:12])[cH:13][cH:14][c:19]1[OH:15].n1[cH:8][cH:1][nH][cH:28]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH2:7][c:8]1[cH:9][cH:10][c:11]([Br:12])[cH:13][cH:14]1)[O:15][Si:16]([CH3:17])([CH2:18][c:19]1[cH:20][cH:21][c:22]([Br:23])[cH:... | CC(C)(C)[Si](C)(C)Cl.Oc1ccc(Br)cc1.c1c[nH]cn1 | CC(C)(C)[Si](C)(Cc1ccc(Br)cc1)O[Si](C)(Cc1ccc(Br)cc1)C(C)(C)C | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 0f959fe0beca926e96ada3da9e557256437f5c27bef02648c5d902ac520e91a2 | 328decf7a2b49d6f133f94d969c3f20d9991077f44a80a10d44297307471aa9c | c1ccc(C[SiH2]O[SiH2]Cc2ccccc2)cc1 | Cl-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[CH3;D1;+0:3])-[C;H0;D4;+0:4](-[C;D1;H3:5])(-[CH3;D1;+0:6])-[CH3;D1;+0:7].[OH;D1;+0:8]-[c;H0;D3;+0:9]1:[cH;D2;+0:10]:[c:11]:[c:12]:[c:13]:[cH;D2;+0:14]:1.[cH;D2;+0:15]1:[cH;D2;+0:16]:n:[cH;D2;+0:17]:[nH]:1>>[C;D1;H3:18]-[#14:19](-[C:20]-[c;H0;D3;+0:9](:[c:21]:[c:22]):[c:23]:[c:24])(-[O... | null | [] | null | null | null | null | 4-Bromophenol (5.76 g, 30 mmol), imidazole (4.08 g, 60 mmol) and tert-butyldimethylsilyl chloride (5.02 g, 33 mmol) were stirred in anhydrous DMF (100 mL) at 25° C. for 18 h. The reaction mixture was then poured into water (100 mL) and extracted with ethyl acetate (2×75 mL). The combined extracts were washed with water... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Silyl protective group | Aromatic halide.Silyl protective group.Silyl protective group | c1ccccc1.c1c[nH]cn1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | null | CN(C)C=O | null | null | CC(C)(C)[Si](C)(C)Cl.Oc1ccc(Br)cc1.c1c[nH]cn1>CN(C)C=O>CC(C)(C)[Si](C)(Cc1ccc(Br)cc1)O[Si](C)(Cc1ccc(Br)cc1)C(C)(C)C |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3d6034b340a6469bb00e1992fa10c04a | CN1CCCC1c1cncc(-c2ccc(O[Si](C)(C)C(C)(C)C)cc2)c1>>CN1CCCC1c1cncc(-c2ccc(O)cc2)c1 | [Si](C)(C)(C(C)(C)C)OC1=CC=C(C=C1)C=1C=C(C=NC1)C1N(CCC1)C.[F-].[Cs+]>>OC1=CC=C(C=C1)C=1C=C(C=NC1)C1N(CCC1)C | CC(C)(C)[Si](C)(C)[O:16][c:15]1[cH:14][cH:13][c:12](-[c:11]2[cH:10][n:9][cH:8][c:7]([CH:6]3[N:2]([CH3:1])[CH2:3][CH2:4][CH2:5]3)[cH:19]2)[cH:18][cH:17]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]1[c:7]1[cH:8][n:9][cH:10][c:11](-[c:12]2[cH:13][cH:14][c:15]([OH:16])[cH:17][cH:18]2)[cH:19]1 | CN1CCCC1c1cncc(-c2ccc(O[Si](C)(C)C(C)(C)C)cc2)c1 | CN1CCCC1c1cncc(-c2ccc(O)cc2)c1 | null | null | CO | Deprotection | Alcohol deprotection from silyl ethers | e70131badc7d7d580ed75b2dfb3ce6df2a5f496b2119611cf5354e1267babe73 | b09ece7bccc3ff762f4ff5407ad846fffba6d6a63735853c86a86d29904f54ed | c1ccc(-c2cncc(C3CCCN3)c2)cc1 | C-C(-C)(-C)-[Si](-C)(-C)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 93 | [{"value": 93.0, "product": "OC1=CC=C(C=C1)C=1C=C(C=NC1)C1N(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.5, "product": "OC1=CC=C(C=C1)C=1C=C(C=NC1)C1N(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | The above-described pyridine derivative (750 mg, 2.04 mmol) was dissolved in methanol (40 mL) and cesium fluoride (620 mg, 4.08 mmol) was added. The stirred mixture was heated at reflux for 18 h under inert atmosphere. After cooling the solvent was removed in vacuo and the resulting oil was dissolved in ethyl acetate (... | 10.6084/m9.figshare.5104873.v1 | null | TMS ether protective group | Aromatic alcohol | null | null | C1CC[NH]C1.c1ccncc1.c1ccccc1 | Other | CO | null | null | CN1CCCC1c1cncc(-c2ccc(O[Si](C)(C)C(C)(C)C)cc2)c1>CO>CN1CCCC1c1cncc(-c2ccc(O)cc2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6dce189fe63f4ba0b54cc330e70cd641 | O=C(O)C(F)(F)F.c1ccncc1>>Fc1ccc(-c2cncc(C3CCCCN3)c2)cc1 | N1=CC=CC=C1.FC(C(=O)O)(F)F>>FC1=CC=C(C=C1)C=1C=C(C=NC1)C1NCCCC1 | O=[C:7](O)[C:4](F)(F)[F:1].[cH:2]1[cH:3][cH:9][n:8][cH:15][cH:14]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][cH:9][c:10]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][NH:16]3)[cH:17]2)[cH:18][cH:19]1 | O=C(O)C(F)(F)F.c1ccncc1 | Fc1ccc(-c2cncc(C3CCCCN3)c2)cc1 | null | null | ClCCl | Aromatic Heterocycle Formation | OtherReaction | a8a87a158a2056cf6dbfb85230c0168ccac2f70e8bd65ac5e991d7afb0d13919 | f57d442aef6d0db344d3850f325d74c2ed6a0476807fa32b642769be47e1191e | c1ccc(-c2cncc(C3CCCCN3)c2)cc1 | F-[C;H0;D4;+0:1](-F)(-[F;H0;D1;+0:2])-[C;H0;D3;+0:3](-O)=O.[cH;D2;+0:4]1:[cH;D2;+0:5]:[n;H0;D2;+0:6]:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:1>>[F;H0;D1;+0:2]-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[c:12](-[c:13]2:[c:14]:[c:15](-[C:16]3-[#7:17]-[CH2;D2;+0:5]-[CH2;D2;+0:4]-[C:18]-[C:19]-3):[cH;D2;+0:7]:[n;H0;D2;+0:6]:[cH;D2;+0:3]... | null | [] | 25 | CELSIUS | 18 | HOUR | The above-described pyridine derivative (1.25 g, 3.5 mmol) was dissolved in a mixture of dichloromethane (10 mL) and trifluoroacetic acid (10 mL) and this was stirred at 25° C. for 18 h. The solvents were removed in vacuo and the crude material dissolved in ethyl acetate (50 mL). Saturated sodium carbonate solution (30... | 10.6084/m9.figshare.5104873.v1 | null | Trifluoro group.Carboxylic acid | Aromatic halide.Secondary amine | c1ccncc1 | c1ccccc1.c1ccncc1.C1CCNCC1 | c1ccccc1.c1ccncc1.C1CCNCC1 | null | ClCCl | 25 | 18 | O=C(O)C(F)(F)F.c1ccncc1>ClCCl>Fc1ccc(-c2cncc(C3CCCCN3)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-78d0ff9eaef04c19a3803165f28b1df6 | O=C(O)/C=C/C(=O)O>>O=C(O)/C=C/C(=O)O | N1=CC=CC=C1.C(\C=C\C(=O)O)(=O)O.FC1=CC=C(C=C1)C=1C=C(C=NC1)C1NCCCC1>>C(\C=C\C(=O)O)(=O)O.FC1=CC=C(C=C1)C=1C=C(C=NC1)C1NCCCC1 | [O:20]=[C:21]([OH:22])/[CH:23]=[CH:24]/[C:25](=[O:26])[OH:27]>>[O:20]=[C:21]([OH:22])/[CH:23]=[CH:24]/[C:25](=[O:26])[OH:27] | O=C(O)/C=C/C(=O)O | O=C(O)/C=C/C(=O)O | null | null | CO | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | null | null | 70 | [{"value": 70.0, "product": "C(\\C=C\\C(=O)O)(=O)O.FC1=CC=C(C=C1)C=1C=C(C=NC1)C1NCCCC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | The above described pyridine derivative was converted into invention compound of Formula I by the addition of one equivalent of fumaric acid to a methanol (15 mL) solution of the free amine at 25° C. After 30 minutes the solvent was removed in vacuo and the residue pumped under high vacuum. Trituration with diethyl eth... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | null | null | CO | null | null | O=C(O)/C=C/C(=O)O>CO>O=C(O)/C=C/C(=O)O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-cab3b5c8094f4cc7bac7b64653997c0e | CN1CCCC1c1cncc(Br)c1.COCCOC>>CC#Cc1cncc(C2CCCN2C)c1 | BrC=1C=C(C=NC1)C1N(CCC1)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+].COCCOC>>C(#CC)C=1C=C(C=NC1)C1N(CCC1)C | Br[c:4]1[cH:5][n:6][cH:7][c:8]([CH:9]2[CH2:10][CH2:11][CH2:12][N:13]2[CH3:14])[cH:15]1.COC[CH2:2]O[CH3:1]>>[CH3:1][C:2]#[C:3][c:4]1[cH:5][n:6][cH:7][c:8]([CH:9]2[CH2:10][CH2:11][CH2:12][N:13]2[CH3:14])[cH:15]1 | CN1CCCC1c1cncc(Br)c1.COCCOC | CC#Cc1cncc(C2CCCN2C)c1 | null | [Pd].[Cu]I | O | C-C Coupling | OtherReaction | a32a56bed9025f72117198f4e933df45b4281747e0549a7040af0b567c3d10eb | 7f5d32d1634bdedad0ee6775d65e5ccb1fbe91d490e3534a585699fa8bc13923 | c1cncc(C2CCCN2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.C-O-C-[CH2;D2;+0:7]-O-[CH3;D1;+0:8]>>[CH3;D1;+0:8]-[C;H0;D2;+0:7]#[C:9]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 312.1 | [{"value": 30.0, "product": "C(#CC)C=1C=C(C=NC1)C1N(CCC1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 312.1, "product": "C(#CC)C=1C=C(C=NC1)C1N(CCC1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | null | null | A Parr hydrogenation vessel was charged with 5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine (1 g, 4.15 mmol), 10% palladium on charcoal (106 mg, 0.1 mmol), copper(I)iodide (38 mg, 0.2 mmol), triphenylphosphine (104 mg, 0.4 mmol) and potassium carbonate (1.38 g, 10 mmol), DME (10 mL) and water (10 mL). The vessel was evacu... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Ether.Ether | Alkyne | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CC[NH]C1 | HBr | [Pd].[Cu]I.O | 90 | null | CN1CCCC1c1cncc(Br)c1.COCCOC>[Pd].[Cu]I.O>CC#Cc1cncc(C2CCCN2C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9501c188203f4630b6447cbfdf010c16 | C#CC(C)(C)O.CC(C)(C)OC(=O)N1CCCC1c1cncc(Br)c1>>C#CC(C)(O)Cc1cncc(C2CCCN2C(=O)OC(C)(C)C)c1 | BrC=1C=C(C=NC1)C1N(CCC1)C(=O)OC(C)(C)C.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C([O-])([O-])=O.[K+].[K+].CC(C)(C#C)O>>OC(CC=1C=C(C=NC1)C1N(CCC1)C(=O)OC(C)(C)C)(C#C)C | [CH:1]#[C:2][C:3]([CH3:4])([OH:5])[CH3:6].Br[c:7]1[cH:8][n:9][cH:10][c:11]([CH:12]2[CH2:13][CH2:14][CH2:15][N:16]2[C:17](=[O:18])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[cH:24]1>>[CH:1]#[C:2][C:3]([CH3:4])([OH:5])[CH2:6][c:7]1[cH:8][n:9][cH:10][c:11]([CH:12]2[CH2:13][CH2:14][CH2:15][N:16]2[C:17](=[O:18])[O:19][C:20]([... | C#CC(C)(C)O.CC(C)(C)OC(=O)N1CCCC1c1cncc(Br)c1 | C#CC(C)(O)Cc1cncc(C2CCCN2C(=O)OC(C)(C)C)c1 | null | [Pd].[Cu]I | COCCOC.O.C(C)(=O)OCC | C-C Coupling | beta C(sp3) arylation | 8f95a6a4dbf65d683dbaed1144079febc7be23de24a7c40bb0b3588067e89135 | 48892094855745f5c51f8910c27ce7c101e08ad3f9da2a58d5512e3d9c1b432f | c1cncc(C2CCCN2)c1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[C;D1;H1:7]#[C:8]-[C:9](-[C;D1;H3:10])(-[CH3;D1;+0:11])-[O;D1;H1:12]>>[C;D1;H1:7]#[C:8]-[C:9](-[C;D1;H3:10])(-[O;D1;H1:12])-[CH2;D2;+0:11]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | 76.4 | [{"value": 76.0, "product": "OC(CC=1C=C(C=NC1)C1N(CCC1)C(=O)OC(C)(C)C)(C#C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.4, "product": "OC(CC=1C=C(C=NC1)C1N(CCC1)C(=O)OC(C)(C)C)(C#C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | null | null | A mixture of 5-bromo-3-(1-tert-butyloxycarbonyl-2-pyrrolidinyl)pyridine (1 g, 3.06 mmol), 10% palladium on charcoal (80 mg, 0.077 mmol), copper(I)iodide (58 mg, 0.30 mmol), triphenylphosphine (80 mg, 0.30 mmol) and potassium carbonate (1.06 g, 7.65 mmol) in DME (5 mL) and water (5 mL) was stirred at 25° C. After 0.75 h... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | null | c1ccncc1 | c1ccncc1 | c1ccncc1.C1CC[NH]C1 | HBr | [Pd].[Cu]I.COCCOC.O.C(C)(=O)OCC | 25 | null | C#CC(C)(C)O.CC(C)(C)OC(=O)N1CCCC1c1cncc(Br)c1>[Pd].[Cu]I.COCCOC.O.C(C)(=O)OCC>C#CC(C)(O)Cc1cncc(C2CCCN2C(=O)OC(C)(C)C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-51f5891122124b97b3adda749c64890a | C#CC(C)(O)Cc1cncc(C2CCCN2C(=O)OC(C)(C)C)c1>>C#Cc1cncc(C2CCCN2C(=O)OC(C)(C)C)c1 | OC(CC=1C=C(C=NC1)C1N(CCC1)C(=O)OC(C)(C)C)(C#C)C.[H-].[Na+].C1(=CC=CC=C1)C.CC(=O)C>>C(#C)C=1C=C(C=NC1)C1N(CCC1)C(=O)OC(C)(C)C | C#C[C:1](C)(O)[CH2:2][c:3]1[cH:4][n:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][N:12]2[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20]1>>[CH:1]#[C:2][c:3]1[cH:4][n:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][CH2:11][N:12]2[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20]1 | C#CC(C)(O)Cc1cncc(C2CCCN2C(=O)OC(C)(C)C)c1 | C#Cc1cncc(C2CCCN2C(=O)OC(C)(C)C)c1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | e0c34d554f1533c02d2a147b68652164a16653ed3c18e090519cc6b4f25028b8 | c9a50ea006ee5a2373f3cee5af655b900834f385f12525a6f2d8d100641dbf3e | c1cncc(C2CCCN2)c1 | C-[C;H0;D4;+0:1](-O)(-C#C)-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[CH;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 61.2 | [{"value": 61.0, "product": "C(#C)C=1C=C(C=NC1)C1N(CCC1)C(=O)OC(C)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.2, "product": "C(#C)C=1C=C(C=NC1)C1N(CCC1)C(=O)OC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | null | null | 5-(2-Hydroxy-2-methyl-3-butynyl)-3-(1-tert-butyloxycarbonyl-2-pyrrolidinyl)pyridine (495 mg, 1.5 mmol) was dissolved in toluene (30 mL) and catalytic sodium hydride (10 mg) was added. The solution was heated until several milliliters of toluene-acetone mixture was removed by distillation. The mixture was cooled to 25° ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Alkyne | Alkyne | null | null | c1ccncc1.C1CC[NH]C1 | HO- | C1(=CC=CC=C1)C | 25 | null | C#CC(C)(O)Cc1cncc(C2CCCN2C(=O)OC(C)(C)C)c1>C1(=CC=CC=C1)C>C#Cc1cncc(C2CCCN2C(=O)OC(C)(C)C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-90e66e44000e45b397f6a1aa0fe837fd | CN1C(=O)C(Br)(Br)CC1c1cncc(Br)c1>>CN1C(=O)CCC1c1cncc(Br)c1 | BrC=1C=C(C=NC1)C1CC(C(N1C)=O)(Br)Br.[Te].[BH4-].[Na+].C(C)(=O)OCC>>BrC=1C=C(C=NC1)C1CCC(N1C)=O | Br[C:5]1(Br)[C:3](=[O:4])[N:2]([CH3:1])[CH:7]([c:8]2[cH:9][n:10][cH:11][c:12]([Br:13])[cH:14]2)[CH2:6]1>>[CH3:1][N:2]1[C:3](=[O:4])[CH2:5][CH2:6][CH:7]1[c:8]1[cH:9][n:10][cH:11][c:12]([Br:13])[cH:14]1 | CN1C(=O)C(Br)(Br)CC1c1cncc(Br)c1 | CN1C(=O)CCC1c1cncc(Br)c1 | null | null | C(C)O | Functional Group Interconversion | OtherReaction | 06e3b15235bbcc563676f888709fdde88f472154a47a559ea324203adaf9701d | 716a56ec5f93782b94d6bb966a574f05066aa2798606ca907a096a9823d2c7c7 | O=C1CCC(c2cccnc2)N1 | Br-[C;H0;D4;+0:1]1(-Br)-[C:2]-[C:3]-[#7:4](-[C;D1;H3:5])-[C:6]-1=[O;D1;H0:7]>>[C;D1;H3:5]-[#7:4]1-[C:3]-[C:2]-[CH2;D2;+0:1]-[C:6]-1=[O;D1;H0:7] | 68 | [{"value": 68.0, "product": "BrC=1C=C(C=NC1)C1CCC(N1C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 67.9, "product": "BrC=1C=C(C=NC1)C1CCC(N1C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | Sodium borohydride (862 mg, 22.8 mmol) was dissolved in ethanol (20 mL) and tellurium metal powder (1.45 g, 11.4 mmol) was added in portions. The mixture was heated under reflux for 0.25 h and 5-bromo-3-(3,3-dibromo-1-methyl-5-pyrrolidin-2-onyl)pyridine (775 mg, 1.9 mmol) was added to the solution at 25° C. After stirr... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide | null | C1CC[NH]C1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccncc1 | Br- | C(C)O | null | 2 | CN1C(=O)C(Br)(Br)CC1c1cncc(Br)c1>C(C)O>CN1C(=O)CCC1c1cncc(Br)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-531fb851617d486f9d7f9ae162bfa0c1 | C#CC(C)(O)Cc1cncc(C2CCC(=O)N2C)c1>>C#Cc1cncc(C2CCC(=O)N2C)c1 | OC(CC=1C=C(C=NC1)C1CCC(N1C)=O)(C#C)C.[H-].[Na+].C1(=CC=CC=C1)C.CC(=O)C>>C(#C)C=1C=C(C=NC1)C1CCC(N1C)=O | C#C[C:1](C)(O)[CH2:2][c:3]1[cH:4][n:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][C:11](=[O:12])[N:13]2[CH3:14])[cH:15]1>>[CH:1]#[C:2][c:3]1[cH:4][n:5][cH:6][c:7]([CH:8]2[CH2:9][CH2:10][C:11](=[O:12])[N:13]2[CH3:14])[cH:15]1 | C#CC(C)(O)Cc1cncc(C2CCC(=O)N2C)c1 | C#Cc1cncc(C2CCC(=O)N2C)c1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | e0c34d554f1533c02d2a147b68652164a16653ed3c18e090519cc6b4f25028b8 | c9a50ea006ee5a2373f3cee5af655b900834f385f12525a6f2d8d100641dbf3e | O=C1CCC(c2cccnc2)N1 | C-[C;H0;D4;+0:1](-O)(-C#C)-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7]>>[CH;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]:[#7;a:6]:[c:7] | 81.1 | [{"value": 81.0, "product": "C(#C)C=1C=C(C=NC1)C1CCC(N1C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 81.1, "product": "C(#C)C=1C=C(C=NC1)C1CCC(N1C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 25 | CELSIUS | null | null | 5-(2-Hydroxy-2-methyl-3-butynyl)-3-(1-methyl-5-pyrrolidin-2-onyl)pyridine (200 mg, 0.77 mmol) was dissolved in toluene (20 mL) and catalytic sodium hydride (5 mg) was added. The solution was heated until several milliliters of toluene-acetone mixture were removed by distillation. The mixture was cooled to 25° C. and wa... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary alcohol.Alkyne | Alkyne | null | null | c1ccncc1.C1CC[NH]C1 | HO- | C1(=CC=CC=C1)C | 25 | null | C#CC(C)(O)Cc1cncc(C2CCC(=O)N2C)c1>C1(=CC=CC=C1)C>C#Cc1cncc(C2CCC(=O)N2C)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f41d5311eb5f4af8a6285626321fd3d2 | Brc1cncc(N2C=CCC2)c1>>Brc1cncc(C2CCCN2)c1 | [BH4-].[Na+].C(=O)(OCC1=CC=CC=C1)N1[C@H](C(=O)O)CCC1.BrC=1C=C(C=NC1)N1C=CCC1.C(=O)(OCC1=CC=CC=C1)N1[C@H](C(=O)O)CCC1>>BrC=1C=C(C=NC1)C1NCCC1 | [Br:1][c:2]1[cH:3][n:4][cH:5][c:6]([N:11]2[CH:7]=[CH:8][CH2:9][CH2:10]2)[cH:12]1>>[Br:1][c:2]1[cH:3][n:4][cH:5][c:6]([CH:7]2[CH2:8][CH2:9][CH2:10][NH:11]2)[cH:12]1 | Brc1cncc(N2C=CCC2)c1 | Brc1cncc(C2CCCN2)c1 | null | null | COCCOC.C(Cl)Cl | Miscellaneous | OtherReaction | d3491f81d9e4014af9d583ce7f1eebd3f9b8fafb2edbfc204469f78b980a71cb | b676416ed64bee2703b25cfce23c2d729637614b49d16c9747d822896840232f | c1cncc(C2CCCN2)c1 | [#7;a:1]1:[c:2]:[c:3]:[c:4]:[c;H0;D3;+0:5](-[N;H0;D3;+0:6]2-[C:7]-[C:8]-[CH;D2;+0:9]=[CH;D2;+0:10]-2):[c:11]:1>>[#7;a:1]1:[c:2]:[c:3]:[c:4]:[c;H0;D3;+0:5](-[CH;D3;+0:10]2-[CH2;D2;+0:9]-[C:8]-[C:7]-[NH;D2;+0:6]-2):[c:11]:1 | 72.2 | [{"value": 72.0, "product": "BrC=1C=C(C=NC1)C1NCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.2, "product": "BrC=1C=C(C=NC1)C1NCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | Carbobenzyloxy-L-proline (37.4 g, 150 mmol) was dissolved in DME (100 mL) and cooled to 0° C. with stirring. Sodium borohydride (1.89 g, 50 mmol) was added in portions (gas evolution) and the resulting mixture was stirred for 2 h at 25° C. affording a colorless solution. The solvents were removed in vacuo and the resut... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Secondary amine | c1ccncc1.C1=C[NH]CC1 | c1ccncc1.C1CCNC1 | c1ccncc1.C1CCNC1 | null | COCCOC.C(Cl)Cl | 0 | null | Brc1cncc(N2C=CCC2)c1>COCCOC.C(Cl)Cl>Brc1cncc(C2CCCN2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-517e4912474b4ef3a1a63cf226e5a44c | Brc1cncc(C2CCCN2)c1>>CN1CCCC1c1cncc(Br)c1 | BrC=1C=C(C=NC1)C1NCCC1.C(=O)O>>BrC=1C=C(C=NC1)C1N(CCC1)C | [NH:2]1[CH2:3][CH2:4][CH2:5][CH:6]1[c:7]1[cH:8][n:9][cH:10][c:11]([Br:12])[cH:13]1>>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][CH:6]1[c:7]1[cH:8][n:9][cH:10][c:11]([Br:12])[cH:13]1 | Brc1cncc(C2CCCN2)c1 | CN1CCCC1c1cncc(Br)c1 | null | null | C=O | Miscellaneous | OtherReaction | 8e80b4f4b7042b748282a2f4c695bd44912d6f8b26c2523ed95efd55cabd75a9 | 06e4cfdff0e70e885199cc5de7382cc871277954ed1dd9750edc3ce3b12c44bd | c1cncc(C2CCCN2)c1 | [#7;a:1]:[c:2]:[c:3]-[C:4]1-[C:5]-[C:6]-[C:7]-[NH;D2;+0:8]-1>>[#7;a:1]:[c:2]:[c:3]-[C:4]1-[C:5]-[C:6]-[C:7]-[N;H0;D3;+0:8]-1-[C;D1;H3:9] | null | [] | 80 | CELSIUS | 3 | HOUR | Enantiomerically enriched 5-bromo-3-(2-pyrrolidinyl)pyridine (1.82 g, 8 mmol) was dissolved in a mixture of 98% formic acid (16 mL) and 37% aqueous formaldehyde (8 mL). The solution was heated with stirring for 3 h at 80° C. After cooling to 25° C. the mixture was concentrated in vacuo and water (30 mL) added. The mixt... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amine | Tertiary amine | C1CCNC1 | C1CC[NH]C1 | C1CC[NH]C1.c1ccncc1 | Other | C=O | 80 | 3 | Brc1cncc(C2CCCN2)c1>C=O>CN1CCCC1c1cncc(Br)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2e59b47848294fe195989e641f0b30fb | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CCC#N)oc2c1.[N-]=[N+]=[N-]>>Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CCc3nnn[nH]3)oc2c1 | C(#N)CCC=1OC2=C(C1)C=CC(=C2)OCC=2N=C(OC2C)C2=CC=CC=C2.[N-]=[N+]=[N-].[Na+].[Cl-].[NH4+].CN(C=O)C>>CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)CCC2=NN=NN2)C=C1 | [CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]2[cH:19][c:20]([CH2:21][CH2:22][C:23]#[N:24])[o:28][c:29]2[cH:30]1.[N-:25]=[N+:26]=[N-:27]>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][c:15]1[cH:16][cH:1... | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CCC#N)oc2c1.[N-]=[N+]=[N-] | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CCc3nnn[nH]3)oc2c1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | 237b84aaa459abf427f233dc6a07a1d9de824f980714e458423189bb68f60f12 | d8c808528b7ee68720aaeebd35cb6a2a30e344748d0066102cdae99843b93cf0 | c1ccc(-c2nc(COc3ccc4cc(CCc5nnn[nH]5)oc4c3)co2)cc1 | [C:1]-[C:2]-[C;H0;D2;+0:3]#[N;H0;D1;+0:4].[N-;H0;D1:5]=[N+;H0;D2:6]=[N-;H0;D1:7]>>[C:1]-[C:2]-[c;H0;D3;+0:3]1:[n;H0;D2;+0:4]:[n;H0;D2;+0:5]:[n;H0;D2;+0:6]:[nH;D2;+0:7]:1 | 78.1 | [{"value": 78.0, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)CCC2=NN=NN2)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.1, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)CCC2=NN=NN2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture of 2-(2-cyanoethyl)-6-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzofuran (1.20 g), sodium azide (1.09 g), ammonium chloride (0.90 g) and N,N-dimethylformamide (30 ml) was stirred at 130° to 140° C. for 16 hours. The reaction mixture was poured over water and extracted with ethyl acetate. After the ethyl acetate ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | null | null | c1nnn[nH]1 | c1cocn1.c1ccccc1.c1ccc2occc2c1.c1nnn[nH]1 | null | O | null | 16 | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CCC#N)oc2c1.[N-]=[N+]=[N-]>O>Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CCc3nnn[nH]3)oc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f01dc9a32ad94d4099a32d40a2b8c964 | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C=C3SC(=O)NC3=O)oc2c1>>Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CC3SC(=O)NC3=O)oc2c1 | CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)C=C2C(NC(S2)=O)=O)C=C1>>CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)CC2C(NC(S2)=O)=O)C=C1 | [CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]2[cH:19][c:20]([CH:21]=[C:22]3[S:23][C:24](=[O:25])[NH:26][C:27]3=[O:28])[o:29][c:30]2[cH:31]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][c:15]1[cH:16][... | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C=C3SC(=O)NC3=O)oc2c1 | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CC3SC(=O)NC3=O)oc2c1 | null | [C].[Pd] | O1CCCC1 | Reduction | Hydrogenation (double to single) | 5287357a9ceae46aa07f85d3bac2070fe5bb40eaa8eb1baec18cbe42a25e8909 | 229264280d760663074461f898bce2a68d1dd7a993ad956085f2c6522e0edd11 | O=C1NC(=O)C(Cc2cc3ccc(OCc4coc(-c5ccccc5)n4)cc3o2)S1 | [O;D1;H0:1]=[C:2]1-[#16:3]-[C;H0;D3;+0:4](=[CH;D2;+0:5]-[c:6](:[c:7]):[#8;a:8]:[c:9])-[C:10](=[O;D1;H0:11])-[#7:12]-1>>[O;D1;H0:1]=[C:2]1-[#16:3]-[CH;D3;+0:4](-[CH2;D2;+0:5]-[c:6](:[c:7]):[#8;a:8]:[c:9])-[C:10](=[O;D1;H0:11])-[#7:12]-1 | 38 | [{"value": 38.0, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)CC2C(NC(S2)=O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.9, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)CC2C(NC(S2)=O)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture of 5-[6-(5-methyl-2-phenyl-4-oxazolyl-methoxy)-2-benzofuranylmethylidene]-2,4-thiazolidinedione (0.80 g), palladium-carbon (5%, 1.60 g) and tetrahydrofuran (250 ml) was subjected to catalytic reduction at room temperature under a hydrogen pressure of 3.2 kgf/cm2 for 8 hours. After the catalyst was filtered of... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Monosulfide | C1CSCN1 | C1CSCN1 | c1cocn1.c1ccccc1.c1ccc2occc2c1.C1CSCN1 | null | [C].[Pd].O1CCCC1 | null | 16 | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C=C3SC(=O)NC3=O)oc2c1>[C].[Pd].O1CCCC1>Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CC3SC(=O)NC3=O)oc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-76206d3ad92c4c3493b9dddaa1158ad8 | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C=O)oc2c1.O=C1COC(=O)N1>>Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CC3OC(=O)NC3=O)oc2c1 | CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)C=O)C=C1.O1C(NC(C1)=O)=O.N1CCCC1.C(C)O>>CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)CC2C(NC(O2)=O)=O)C=C1 | O=[CH:21][c:20]1[cH:19][c:18]2[cH:17][cH:16][c:15]([O:14][CH2:13][c:12]3[c:2]([CH3:1])[o:3][c:4](-[c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[n:11]3)[cH:31][c:30]2[o:29]1.[CH2:22]1[O:23][C:24](=[O:25])[NH:26][C:27]1=[O:28]>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][c:15]1[c... | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C=O)oc2c1.O=C1COC(=O)N1 | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CC3OC(=O)NC3=O)oc2c1 | null | null | O | C-C Coupling | OtherReaction | 33836e860df20f020a80983ec1dc6ecf2560632bbfe5ada8cdc3a4801998d112 | bf4569804906d66c98adaac7df334e96eee508d45c26c621eb5069c3e4f1df77 | O=C1NC(=O)C(Cc2cc3ccc(OCc4coc(-c5ccccc5)n4)cc3o2)O1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#8;a:4]:[c:5].[O;D1;H0:6]=[C:7]1-[#7:8]-[C:9](=[O;D1;H0:10])-[CH2;D2;+0:11]-[#8:12]-1>>[O;D1;H0:6]=[C:7]1-[#7:8]-[C:9](=[O;D1;H0:10])-[CH;D3;+0:11](-[CH2;D2;+0:1]-[c:2](:[c:3]):[#8;a:4]:[c:5])-[#8:12]-1 | 6.6 | [{"value": 6.6, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)CC2C(NC(O2)=O)=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 6.6, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)CC2C(NC(O2)=O)=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofurancarbaldehyde (1.70 g), 2,4-oxazolidinedione (1.55 g), pyrrolidine (0.365 g) and ethanol (40 ml) was heated under refluxing conditions for 3 hours. The reaction mixture was poured over water; the resulting crystals were collected by filtration. The crystal... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether | Ether | C1COCN1 | C1COCN1 | c1cocn1.c1ccccc1.c1ccc2occc2c1.C1COCN1 | Other | O | null | null | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C=O)oc2c1.O=C1COC(=O)N1>O>Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CC3OC(=O)NC3=O)oc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-87b01b59f727440086967c46a538d8dc | CCOP(=O)(CC#N)OCC.Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C=O)oc2c1>>Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CCC#N)oc2c1 | [H-].[Na+].CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)C=O)C=C1.C(#N)CP(OCC)(OCC)=O.Cl>>C(#N)CCC=1OC2=C(C1)C=CC(=C2)OCC=2N=C(OC2C)C2=CC=CC=C2 | CCOP(=O)(OCC)[CH2:22][C:23]#[N:24].O=[CH:21][c:20]1[cH:19][c:18]2[cH:17][cH:16][c:15]([O:14][CH2:13][c:12]3[c:2]([CH3:1])[o:3][c:4](-[c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[n:11]3)[cH:27][c:26]2[o:25]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][c:15]1[cH:16][cH:17][c:18... | CCOP(=O)(CC#N)OCC.Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C=O)oc2c1 | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CCC#N)oc2c1 | null | null | CN(C=O)C | C-C Coupling | OtherReaction | 43d4e2f03e758941ee99f59641d5d56e6475fe935434d251d75d5cdebbe19869 | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | c1ccc(-c2nc(COc3ccc4ccoc4c3)co2)cc1 | C-C-O-P(=O)(-O-C-C)-[CH2;D2;+0:1]-[C:2]#[N;D1;H0:3].O=[CH;D2;+0:4]-[c:5](:[c:6]):[#8;a:7]:[c:8]>>[N;D1;H0:3]#[C:2]-[CH2;D2;+0:1]-[CH2;D2;+0:4]-[c:5](:[c:6]):[#8;a:7]:[c:8] | 83.1 | [{"value": 83.0, "product": "C(#N)CCC=1OC2=C(C1)C=CC(=C2)OCC=2N=C(OC2C)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 83.1, "product": "C(#N)CCC=1OC2=C(C1)C=CC(=C2)OCC=2N=C(OC2C)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Sodium hydride (60%, oily, 0.20 g) was gradually added to a solution of 6-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzofuran-2-carbaldehyde (1.50 g) and diethyl cyanomethylphosphonate (0.88 g) in N,N-dimethylformamide (30 ml) at 0° C., followed by stirring at room temperature for 1 hour. The reaction mixture was poured ov... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | null | null | c1cocn1.c1ccccc1.c1ccc2occc2c1 | HO- | CN(C=O)C | null | 1 | CCOP(=O)(CC#N)OCC.Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C=O)oc2c1>CN(C=O)C>Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CCC#N)oc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-647fc8886f5443968e4362c127da55fe | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C=O)oc2c1.N#CCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>>Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CCCCC#N)oc2c1 | [H-].[Na+].[Br-].C(#N)CCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.Cl.CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)C=O)C=C1>>C(#N)CCCCC=1OC2=C(C1)C=CC(=C2)OCC=2N=C(OC2C)C2=CC=CC=C2 | O=[CH:21][c:20]1[cH:19][c:18]2[cH:17][cH:16][c:15]([O:14][CH2:13][c:12]3[c:2]([CH3:1])[o:3][c:4](-[c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[n:11]3)[cH:29][c:28]2[o:27]1.c1ccc([P+](c2ccccc2)(c2ccccc2)[CH2:22][CH2:23][CH2:24][C:25]#[N:26])cc1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH... | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C=O)oc2c1.N#CCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1 | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CCCCC#N)oc2c1 | null | [C].[Pd] | CN(C=O)C.O1CCCC1 | C-C Coupling | OtherReaction | cb5f277ac55a0e763ef643becc05f1522019cc4161daceb249ed2d634b78153b | cedc9d4b791e43eacf8e7ecfa6a98d1dc0438794e96e4f1c4bef436b78f82bd8 | c1ccc(-c2nc(COc3ccc4ccoc4c3)co2)cc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[#8;a:4]:[c:5].[C:6]-[C:7]-[CH2;D2;+0:8]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1>>[C:6]-[C:7]-[CH2;D2;+0:8]-[CH2;D2;+0:1]-[c:2](:[c:3]):[#8;a:4]:[c:5] | 60 | [{"value": 60.0, "product": "C(#N)CCCCC=1OC2=C(C1)C=CC(=C2)OCC=2N=C(OC2C)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.8, "product": "C(#N)CCCCC=1OC2=C(C1)C=CC(=C2)OCC=2N=C(OC2C)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | Sodium hydride (60%, oily, 0.20 g) was gradually added to a solution of 3-cyanopropyltriphenylphosphonium bromide (2.07 g) in N,N-dimethylformamide (30 ml) at room temperature, followed by stirring for 1 hour. 6-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzofuran-2-carboaldehyde (1.40 g) was added, followed by stirring at ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | c1cocn1.c1ccccc1.c1ccc2occc2c1 | HO- | [C].[Pd].CN(C=O)C.O1CCCC1 | null | 1 | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C=O)oc2c1.N#CCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1>[C].[Pd].CN(C=O)C.O1CCCC1>Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CCCCC#N)oc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-667e2aee4c9a4838b14ae6bea3b0b581 | Cc1oc(-c2ccccc2)nc1COc1ccc2oc(CCCO)cc2c1.[C-]#N>>Cc1oc(-c2ccccc2)nc1COc1ccc2oc(CCCC#N)cc2c1 | CC1=C(N=C(O1)C1=CC=CC=C1)COC=1C=CC2=C(C=C(O2)CCCO)C1.[C-]#N.[Na+]>>C(#N)CCCC=1OC2=C(C1)C=C(C=C2)OCC=2N=C(OC2C)C2=CC=CC=C2 | O[CH2:23][CH2:22][CH2:21][c:20]1[o:19][c:18]2[cH:17][cH:16][c:15]([O:14][CH2:13][c:12]3[c:2]([CH3:1])[o:3][c:4](-[c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[n:11]3)[cH:28][c:27]2[cH:26]1.[C-:24]#[N:25]>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]2[o... | Cc1oc(-c2ccccc2)nc1COc1ccc2oc(CCCO)cc2c1.[C-]#N | Cc1oc(-c2ccccc2)nc1COc1ccc2oc(CCCC#N)cc2c1 | null | null | null | C-C Coupling | OtherReaction | a1e85c1b3a4aa1231f3779c2baa8b6951b270c05216d065e2aa7ce489240e0a5 | 1d32632fcc69ac04f0b8d96dc5305dd07d5339ab86bfe9a364cefb5e65c6d5b1 | c1ccc(-c2nc(COc3ccc4occc4c3)co2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[C:3].[C-;H0;D1:4]#[N;D1;H0:5]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[C;H0;D2;+0:4]#[N;D1;H0:5] | 80 | [{"value": 80.0, "product": "C(#N)CCCC=1OC2=C(C1)C=C(C=C2)OCC=2N=C(OC2C)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In the same manner as in Example 13, 3-[5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]propanol was mesylated and then reacted with sodium cyanide to yield 2-(3-cyanopropyl)-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzofuran (yield 80%), which was then recrystallized from acetone-isopropyl ether to yield colorle... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Nitrile | null | null | c1cocn1.c1ccccc1.c1ccc2occc2c1 | HO- | null | null | null | Cc1oc(-c2ccccc2)nc1COc1ccc2oc(CCCO)cc2c1.[C-]#N>>Cc1oc(-c2ccccc2)nc1COc1ccc2oc(CCCC#N)cc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-4b3d1be49f204b63a88b6e40011ab757 | COC(=O)COc1cc(OC)ccc1C=O>>COC(=O)c1cc2ccc(OC)cc2o1 | C(=O)C1=C(OCC(=O)OC)C=C(C=C1)OC.C1CCC2=NCCCN2CC1>>COC1=CC2=C(C=C(O2)C(=O)OC)C=C1 | O=[CH:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][c:14]1[O:15][CH2:5][C:3]([O:2][CH3:1])=[O:4]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][c:14]2[o:15]1 | COC(=O)COc1cc(OC)ccc1C=O | COC(=O)c1cc2ccc(OC)cc2o1 | null | null | C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 64c067c002cd2d6d34703a3924071fac3d72722f06b3266a78d9ea4e5945bd33 | a2e795ae3b5f0274e22eb9f5b8f51b97c0dcb20cf7c0b4571dec4829087d5b28 | c1ccc2occc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-[CH2;D2;+0:6]-[C:7](=[O;D1;H0:8])-[#8:9]-[C;D1;H3:10]):[c:11]>>[C;D1;H3:10]-[#8:9]-[C:7](=[O;D1;H0:8])-[c;H0;D3;+0:6]1:[cH;D2;+0:1]:[c:2](:[c:3]):[c:4](:[c:11]):[o;H0;D2;+0:5]:1 | 57 | [{"value": 57.0, "product": "COC1=CC2=C(C=C(O2)C(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 56.1, "product": "COC1=CC2=C(C=C(O2)C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of methyl 2-formyl-5-methoxyphenoxyacetate (27.7 g), 1,8-diazabicyclo[5.4.0]-7-undecene (40.8 g) and toluene (200 ml) was heated under refluxing conditions for 4 hours. The reaction mixture was concentrated under reduced pressure; after 6N hydrochloric acid was added, the residue was extracted with ethyl acet... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ester.Ether | Ester | c1ccccc1 | c1ccc2occc2c1 | c1ccc2occc2c1 | HO- | C1(=CC=CC=C1)C | null | null | COC(=O)COc1cc(OC)ccc1C=O>C1(=CC=CC=C1)C>COC(=O)c1cc2ccc(OC)cc2o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c5d94e5973074b06af209206e6641b73 | COC(=O)c1cc2ccc(OC)cc2o1>>COC(=O)c1cc2ccc(O)cc2o1 | C(C)(=O)OCC.B(Br)(Br)Br.COC1=CC2=C(C=C(O2)C(=O)OC)C=C1>>OC1=CC2=C(C=C(O2)C(=O)OC)C=C1 | C[O:11][c:10]1[cH:9][cH:8][c:7]2[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[o:14][c:13]2[cH:12]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][cH:9][c:10]([OH:11])[cH:12][c:13]2[o:14]1 | COC(=O)c1cc2ccc(OC)cc2o1 | COC(=O)c1cc2ccc(O)cc2o1 | null | null | ClCCl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2occc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]:[c:5]:[#8;a:6]>>[#8;a:6]:[c:5]:[c:4]:[c:2](-[OH;D1;+0:1]):[c:3] | 73 | [{"value": 73.0, "product": "OC1=CC2=C(C=C(O2)C(=O)OC)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 10.1, "product": "OC1=CC2=C(C=C(O2)C(=O)OC)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | DAY | Boron tribromide (24.9 g) was added dropwise to a solution of methyl 6-methoxybenzofuran-2-carboxylate (18.6 g) in dichloromethane (200 ml) at 0° C., followed by stirring at room temperature for 1 day. The reaction mixture was poured over ice water; ethyl acetate (300 ml) was added. After the organic layer was washed w... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2occc2c1 | Other | ClCCl | null | 24 | COC(=O)c1cc2ccc(OC)cc2o1>ClCCl>COC(=O)c1cc2ccc(O)cc2o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8d150316356a42dca5493597307eba01 | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CO)oc2c1>>Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C=O)oc2c1 | CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)CO)C=C1>>CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)C=O)C=C1 | [CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]2[cH:19][c:20]([CH2:21][OH:22])[o:23][c:24]2[cH:25]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]2[cH:19][c:20]([CH:21]=[O:22])... | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CO)oc2c1 | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C=O)oc2c1 | null | [O-2].[O-2].[Mn+4] | O1CCCC1 | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc(-c2nc(COc3ccc4ccoc4c3)co2)cc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#8;a:5]:[c:6]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#8;a:5]:[c:6] | 69 | [{"value": 69.0, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)C=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.5, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)C=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 6 | HOUR | A mixture of 6-(5-methyl-2-phenyl-4-oxazolylmethoxy) benzofuran-2-methanol (21.0 g), activated manganese dioxide (52.0 g) and tetrahydrofuran (800 ml) was stirred at 60° to 65° C. for 6 hours. After the insoluble portion was filtered off, the filtrate was concentrated; the residue was subjected to silica gel column chr... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1cocn1.c1ccccc1.c1ccc2occc2c1 | null | [O-2].[O-2].[Mn+4].O1CCCC1 | null | 6 | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CO)oc2c1>[O-2].[O-2].[Mn+4].O1CCCC1>Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C=O)oc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9fb75830acba4d7b95932f5349ef385f | CCOC(=O)/C=C/c1cc2ccc(OCc3nc(-c4ccccc4)oc3C)cc2o1>>Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CCCO)oc2c1 | CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)/C=C/C(=O)OCC)C=C1>>CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)CCCO)C=C1 | CCO[C:23](/[CH:22]=[CH:21]/[c:20]1[cH:19][c:18]2[cH:17][cH:16][c:15]([O:14][CH2:13][c:12]3[c:2]([CH3:1])[o:3][c:4](-[c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[n:11]3)[cH:27][c:26]2[o:25]1)=[O:24]>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]2[cH:19]... | CCOC(=O)/C=C/c1cc2ccc(OCc3nc(-c4ccccc4)oc3C)cc2o1 | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CCCO)oc2c1 | null | [C].[Pd] | O1CCCC1 | Reduction | OtherReaction | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2nc(COc3ccc4ccoc4c3)co2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])/[CH;D2;+0:3]=[CH;D2;+0:4]/[c:5](:[c:6]):[#8;a:7]:[c:8]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[c:5](:[c:6]):[#8;a:7]:[c:8] | null | [] | null | null | null | null | To a solution of (E)-ethyl 3-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]acrylate (1.30 g) in tetrahydrofuran (50 ml), palladium-carbon (5%, 0.70 g) was added, followed by catalytic reduction at room temperature and under an atmospheric pressure of 1 atm. After the catalyst was filtered off, sodium borohydr... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cocn1.c1ccccc1.c1ccc2occc2c1 | Other | [C].[Pd].O1CCCC1 | null | null | CCOC(=O)/C=C/c1cc2ccc(OCc3nc(-c4ccccc4)oc3C)cc2o1>[C].[Pd].O1CCCC1>Cc1oc(-c2ccccc2)nc1COc1ccc2cc(CCCO)oc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-20c9273eacd748b48025e08d9d4eba7a | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C/C=C/O)oc2c1>>Cc1oc(-c2ccccc2)nc1COc1ccc2cc(/C=C/C=O)oc2c1 | CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)C/C=C/O)C=C1>>CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)/C=C/C=O)C=C1 | [CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]2[cH:19][c:20]([CH2:21]/[CH:22]=[CH:23]/[OH:24])[o:25][c:26]2[cH:27]1>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]2[cH:19][c:20... | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C/C=C/O)oc2c1 | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(/C=C/C=O)oc2c1 | null | [O-2].[O-2].[Mn+4] | ClCCl | Miscellaneous | OtherReaction | 85c6819f39bb2d5fd340b3c2674c9b53f845c23a98f4430280d0b76fc6cfbb35 | b5f6e2fa497f4ec01d9746fe00723015e89e6a0a35283ec80319ac80eb48c9dc | c1ccc(-c2nc(COc3ccc4ccoc4c3)co2)cc1 | [OH;D1;+0:1]/[CH;D2;+0:2]=[CH;D2;+0:3]/[CH2;D2;+0:4]-[c:5](:[c:6]):[#8;a:7]:[c:8]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]/[CH;D2;+0:3]=[CH;D2;+0:4]/[c:5](:[c:6]):[#8;a:7]:[c:8] | 89 | [{"value": 89.0, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)/C=C/C=O)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 88.8, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC1=CC2=C(C=C(O2)/C=C/C=O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of (E)-3-[6-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]propen-1-ol (3.85 g), activated manganese dioxide (8.00 g) and dichloromethane (150 ml ) was stirred at room temperature for 2 hours. After the insoluble portion was filtered off, the filtrate was concentrated to yield crystals of (E)-3-[6-(5-me... | 10.6084/m9.figshare.5104873.v1 | null | Enol | Aldehyde | null | null | c1cocn1.c1ccccc1.c1ccc2occc2c1 | null | [O-2].[O-2].[Mn+4].ClCCl | null | 2 | Cc1oc(-c2ccccc2)nc1COc1ccc2cc(C/C=C/O)oc2c1>[O-2].[O-2].[Mn+4].ClCCl>Cc1oc(-c2ccccc2)nc1COc1ccc2cc(/C=C/C=O)oc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-8d8d9084812145079c62beccf28cf5f0 | COC(=O)CBr.COc1ccc(O)c(C=O)c1>>COC(=O)COc1ccc(OC)cc1C=O | COC1=CC=C(C(C=O)=C1)O.BrCC(=O)OC>>C(=O)C1=C(OCC(=O)OC)C=CC(=C1)OC | Br[CH2:5][C:3]([O:2][CH3:1])=[O:4].[OH:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][c:14]1[CH:15]=[O:16]>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][O:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH3:12])[cH:13][c:14]1[CH:15]=[O:16] | COC(=O)CBr.COc1ccc(O)c(C=O)c1 | COC(=O)COc1ccc(OC)cc1C=O | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 50d675b335c583a6ce22e1164b27a78b18b9ca447d45137820c344bcb6369217 | 0865de4e1853c59ac25437e36fd18b03329566cb9eff4b4f0ce70d5714692fd3 | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[O;D1;H0:6]=[C:7]-[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[C;D1;H3:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[O;H0;D2;+0:10]-[c:9](:[c:11]):[c:8]-[C:7]=[O;D1;H0:6] | 86 | [{"value": 86.0, "product": "C(=O)C1=C(OCC(=O)OC)C=CC(=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In the same manner as in Reference Example 1, 5-methoxysalicylaldehyde was reacted with methyl bromoacetate to yield methyl 2-formyl-4-methoxyphenoxyacetate (yield 86%), which was then recrystallized from acetone-hexane to yield colorless prisms having a melting point of 74° to 75° C.
Conditions: See reaction.notes.pro... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Aromatic alcohol | Ester.Ether | null | null | c1ccccc1 | HBr | null | null | null | COC(=O)CBr.COc1ccc(O)c(C=O)c1>>COC(=O)COc1ccc(OC)cc1C=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b3116d4c51654c129518e27f86a5d786 | COC(=O)c1cc2cc(O)ccc2o1.Cc1oc(-c2ccccc2)nc1CCl>>COC(=O)c1cc2cc(OCc3nc(-c4ccccc4)oc3C)ccc2o1 | OC=1C=CC2=C(C=C(O2)C(=O)OC)C1.ClCC=1N=C(OC1C)C1=CC=CC=C1>>CC1=C(N=C(O1)C1=CC=CC=C1)COC=1C=CC2=C(C=C(O2)C(=O)OC)C1 | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([OH:10])[cH:24][cH:25][c:26]2[o:27]1.Cl[CH2:11][c:12]1[n:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[o:21][c:22]1[CH3:23]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]2[cH:8][c:9]([O:10][CH2:11][c:12]3[n:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][cH:2... | COC(=O)c1cc2cc(O)ccc2o1.Cc1oc(-c2ccccc2)nc1CCl | COC(=O)c1cc2cc(OCc3nc(-c4ccccc4)oc3C)ccc2o1 | null | null | null | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(-c2nc(COc3ccc4occc4c3)co2)cc1 | Cl-[CH2;D2;+0:1]-[c:2]1:[#7;a:3]:[c:4]:[#8;a:5]:[c:6]:1-[C;D1;H3:7].[OH;D1;+0:8]-[c:9](:[c:10]):[c:11]>>[C;D1;H3:7]-[c:6]1:[#8;a:5]:[c:4]:[#7;a:3]:[c:2]:1-[CH2;D2;+0:1]-[O;H0;D2;+0:8]-[c:9](:[c:10]):[c:11] | 87 | [{"value": 87.0, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC=1C=CC2=C(C=C(O2)C(=O)OC)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In the same manner as in Reference Example 4, methyl 5-hydroxybenzofuran-2-carboxylate was reacted with 4-chloromethyl-5-methyl-2-phenyloxazole to yield methyl 5-(5-methyl-2-phenyl-4-oxazolylmethoxy)bezofuran-2-carboxylate (yield 87%), which was then recrystallized from acetone-ethyl acetate to yield colorless prisms h... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccc2occc2c1.c1cocn1.c1ccccc1 | HCl | null | null | null | COC(=O)c1cc2cc(O)ccc2o1.Cc1oc(-c2ccccc2)nc1CCl>>COC(=O)c1cc2cc(OCc3nc(-c4ccccc4)oc3C)ccc2o1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-95e24e77c6ef45318b9ed18596119d65 | CCOC(=O)/C=C/c1cc2cc(OCc3nc(-c4ccccc4)oc3C)ccc2o1>>Cc1oc(-c2ccccc2)nc1COc1ccc2oc(/C=C/CO)cc2c1 | CC1=C(N=C(O1)C1=CC=CC=C1)COC=1C=CC2=C(C=C(O2)/C=C/C(=O)OCC)C1.[H-].C(C(C)C)[Al+]CC(C)C>>CC1=C(N=C(O1)C1=CC=CC=C1)COC=1C=CC2=C(C=C(O2)/C=C/CO)C1 | CCO[C:23](/[CH:22]=[CH:21]/[c:20]1[o:19][c:18]2[cH:17][cH:16][c:15]([O:14][CH2:13][c:12]3[c:2]([CH3:1])[o:3][c:4](-[c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[n:11]3)[cH:27][c:26]2[cH:25]1)=[O:24]>>[CH3:1][c:2]1[o:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][cH:9][cH:10]2)[n:11][c:12]1[CH2:13][O:14][c:15]1[cH:16][cH:17][c:18]2[o:19][... | CCOC(=O)/C=C/c1cc2cc(OCc3nc(-c4ccccc4)oc3C)ccc2o1 | Cc1oc(-c2ccccc2)nc1COc1ccc2oc(/C=C/CO)cc2c1 | null | null | null | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(-c2nc(COc3ccc4occc4c3)co2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])/[C:3]=[C:4]/[c:5](:[#8;a:6]):[c:7]>>[#8;a:6]:[c:5](/[C:4]=[C:3]/[CH2;D2;+0:1]-[OH;D1;+0:2]):[c:7] | 90 | [{"value": 90.0, "product": "CC1=C(N=C(O1)C1=CC=CC=C1)COC=1C=CC2=C(C=C(O2)/C=C/CO)C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | In the same manner as in Reference Example 11, (E)-ethyl 3-[5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]acrylate was reduced with diisobutylaluminum hydride to yield (E)-3-[5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]-2-propen-1-ol (yield 90%), which was then recrystallized from ethyl acetate-hexa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1cocn1.c1ccccc1.c1ccc2occc2c1 | HO- | null | null | null | CCOC(=O)/C=C/c1cc2cc(OCc3nc(-c4ccccc4)oc3C)ccc2o1>>Cc1oc(-c2ccccc2)nc1COc1ccc2oc(/C=C/CO)cc2c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a0b0409b86cb49f38ebdef232d24438a | Cc1oc(-c2ccccc2)nc1COc1ccc2oc(/C=C/CO)cc2c1>>Cc1cccc(C(Oc2ccc3oc(CCCO)cc3c2)c2cocn2)c1 | CC1=C(N=C(O1)C1=CC=CC=C1)COC=1C=CC2=C(C=C(O2)/C=C/CO)C1>>CC=1C=CC=C(C1)C(OC=1C=CC2=C(C=C(O2)CCCO)C1)C=1N=COC1 | [CH3:1][c:23]1[c:22]([CH2:7][O:8][c:9]2[cH:10][cH:11][c:12]3[o:13][c:14](/[CH:15]=[CH:16]/[CH2:17][OH:18])[cH:19][c:20]3[cH:21]2)[n:26][c:25](-[c:6]2[cH:5][cH:4][cH:3][cH:2][cH:27]2)[o:24]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH:7]([O:8][c:9]2[cH:10][cH:11][c:12]3[o:13][c:14]([CH2:15][CH2:16][CH2:17][OH:18])[cH:19][... | Cc1oc(-c2ccccc2)nc1COc1ccc2oc(/C=C/CO)cc2c1 | Cc1cccc(C(Oc2ccc3oc(CCCO)cc3c2)c2cocn2)c1 | null | [C].[Pd] | O1CCCC1 | Miscellaneous | OtherReaction | b8803ec569831ffedb8a7c98c3bd8440122b3fb5452083dd296b7420e3c89e86 | bced64702950df7cf56df22d8c2487b007734fece951727fd2c8a1c63fbcf6cc | c1ccc(C(Oc2ccc3occc3c2)c2cocn2)cc1 | [CH3;D1;+0:1]-[c;H0;D3;+0:2]1:[#8;a:3]:[c;H0;D3;+0:4](-[c;H0;D3;+0:5]2:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]:[c:10]:2):[#7;a:11]:[c:12]:1-[CH2;D2;+0:13]-[#8:14]-[c:15].[O;D1;H1:16]-[C:17]/[CH;D2;+0:18]=[CH;D2;+0:19]/[c:20](:[c:21]):[#8;a:22]:[c:23]>>[CH3;D1;+0:1]-[c;H0;D3;+0:7]1:[c:6]:[c;H0;D3;+0:5](-[CH;D3;+0:13](-[#8:14]-[c... | 93 | [{"value": 93.0, "product": "CC=1C=CC=C(C1)C(OC=1C=CC2=C(C=C(O2)CCCO)C1)C=1N=COC1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of (E)-3-[5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofuranyl]-2-propen-1-ol (2.00 g) in tetrahydrofuran (100 ml), palladium-carbon (5%, 0.30 g) was added, followed by catalytic reduction at room temperature and under an atmospheric pressure of 1 atm. After the catalyst was filtered off, the filtrate w... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Ether | c1cocn1.c1ccccc1 | c1ccccc1.c1cocn1 | c1ccccc1.c1ccc2occc2c1.c1cocn1 | null | [C].[Pd].O1CCCC1 | null | null | Cc1oc(-c2ccccc2)nc1COc1ccc2oc(/C=C/CO)cc2c1>[C].[Pd].O1CCCC1>Cc1cccc(C(Oc2ccc3oc(CCCO)cc3c2)c2cocn2)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9e829672ee641d4912a1f2c034f3d35 | CC(=O)Cl.CSc1ccccc1>>CSc1ccc(C(C)=O)cc1 | [Al+3].[Cl-].[Cl-].[Cl-].C1(=CC=CC=C1)SC.C(C)(=O)Cl>>CC(=O)C1=CC=C(C=C1)SC | Cl[C:7]([CH3:8])=[O:9].[CH3:1][S:2][c:3]1[cH:4][cH:5][cH:6][cH:10][cH:11]1>>[CH3:1][S:2][c:3]1[cH:4][cH:5][c:6]([C:7]([CH3:8])=[O:9])[cH:10][cH:11]1 | CC(=O)Cl.CSc1ccccc1 | CSc1ccc(C(C)=O)cc1 | null | null | C(Cl)Cl | C-C Coupling | Friedel-Crafts acylation | 55541449ad4f182ef3dc0497085b282b1dcb76e0fb5ed140dc4eab4973eacb28 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccccc1 | Cl-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:[c:8]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:6](:[c:5]:[c:4]):[c:7]:[c:8] | 88.1 | [{"value": 88.1, "product": "CC(=O)C1=CC=C(C=C1)SC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | 123 g (0.92 mol) of AlCl3 are added with a spatula to a mixture of 100 g (0.8 mol) of thioanisole, 750 ml of CH2Cl2 and 63 ml (0.9 mol) of acetyl chloride, cooled to 0° C. beforehand, said addition being carried out so that the temperature does not exceed 10° C. The mixture is stirred for 1 h at room temperature, heate... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccccc1 | c1ccccc1 | c1ccccc1 | HCl | C(Cl)Cl | 0 | 1 | CC(=O)Cl.CSc1ccccc1>C(Cl)Cl>CSc1ccc(C(C)=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-6d44d87ee23a4984ad13cff1877a23a4 | CSc1ccc(C(C)=O)cc1.[O]=[Mn](=[O])(=[O])[O-]>>CC(=O)c1ccc(S(C)(=O)=O)cc1 | C(C)(=O)O.[O-][Mn](=O)(=O)=O.[K+].CC(=O)C1=CC=C(C=C1)SC.S(=O)([O-])[O-].[Na+].[Na+]>>CC(=O)C1=CC=C(C=C1)S(=O)(=O)C | [CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([S:8][CH3:9])[cH:12][cH:13]1.[O]=[Mn]([O-])(=[O:10])=[O:11]>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7]([S:8]([CH3:9])(=[O:10])=[O:11])[cH:12][cH:13]1 | CSc1ccc(C(C)=O)cc1.[O]=[Mn](=[O])(=[O])[O-] | CC(=O)c1ccc(S(C)(=O)=O)cc1 | null | null | O | Oxidation | OtherReaction | 20dd6d48007b4fe7cd760226f21413eb5e71e6468db112596c2e7ea4858c8ac1 | 5cedc1bf0f43f21d78a249521ecfcec19fc5ac4895c41eed0e84f0c2618149fa | c1ccccc1 | [C;D1;H3:1]-[S;H0;D2;+0:2]-[c:3](:[c:4]):[c:5].[O-]-[Mn](=[O;H0;D1;+0:6])(=[O;H0;D1;+0:7])=[O]>>[C;D1;H3:1]-[S;H0;D4;+0:2](=[O;H0;D1;+0:6])(=[O;H0;D1;+0:7])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 8 | HOUR | A solution of 152 g (0.96 mol) of KMnO4 in 3.5 1 of water is introduced into a mixture of 117.1 g (0.7 mol) of 4-(methylthio)acetophenone, prepared in Example 2c, and 292 ml of acetic acid. 2.3 l of water are added and the reaction temperature is allowed to return to room temperature. Saturated sodium sulfite solution ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide | Sulfone | null | null | c1ccccc1 | Other | O | null | 8 | CSc1ccc(C(C)=O)cc1.[O]=[Mn](=[O])(=[O])[O-]>O>CC(=O)c1ccc(S(C)(=O)=O)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3db0d270f6194dd0b5a468ba8e5ab869 | CCn1ncc(C(=O)c2ccc3c(c2C)C(OC)CCS3(=O)=O)c1O.O=C(Cl)C1CCCCC1>>CCn1ncc(C(=O)c2ccc3c(c2C)C(OC)CCS3(=O)=O)c1OC(=O)C1CCCCC1 | COC1CCS(C2=CC=C(C(=C12)C)C(=O)C=1C=NN(C1O)CC)(=O)=O.N1N=CC=C1.C(C)N(CC)CC.C1(CCCCC1)C(=O)Cl.C([O-])([O-])=O.[Na+].[Na+]>>COC1CCS(C2=CC=C(C(=C12)C)C(=O)C=1C=NN(C1OC(=O)C1CCCCC1)CC)(=O)=O | [CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]3[c:13]([c:14]2[CH3:15])[CH:16]([O:17][CH3:18])[CH2:19][CH2:20][S:21]3(=[O:22])=[O:23])[c:24]1[OH:25].Cl[C:26](=[O:27])[CH:28]1[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]1>>[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:1... | CCn1ncc(C(=O)c2ccc3c(c2C)C(OC)CCS3(=O)=O)c1O.O=C(Cl)C1CCCCC1 | CCn1ncc(C(=O)c2ccc3c(c2C)C(OC)CCS3(=O)=O)c1OC(=O)C1CCCCC1 | null | null | C(Cl)Cl | Acylation | Schotten-Baumann to ester | 1cda078f55e64d9385e544d1067595d5e7672bbd1eff542e7a341817a2d8c4d5 | 6439fc27f97ee9ed7c11ef9b5032d9493d05f28a7bbb50d256a2d54d035fbfb2 | O=C(c1ccc2c(c1)CCCS2(=O)=O)c1cn[nH]c1OC(=O)C1CCCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C:4])-[C:5].[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10](-[C:11]=[O;D1;H0:12]):[c:13]:1-[OH;D1;+0:14]>>[C:4]-[C:3](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:14]-[c:13]1:[#7;a:7](-[C:6]):[#7;a:8]:[c:9]:[c:10]:1-[C:11]=[O;D1;H0:12])-[C:5] | 54 | [{"value": 54.0, "product": "COC1CCS(C2=CC=C(C(=C12)C)C(=O)C=1C=NN(C1OC(=O)C1CCCCC1)CC)(=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | As a starting material, 4-methoxy-5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide corresponding to pyrazole derivative (I-H) was used. 0.4 Gram (1.1 mmol) thereof was dissolved in 4 ml of methylene chloride, and 0.22 g (2.2 mmol) of triethylamine as a base and 0.19 g (1.3 mmol) of cyclohexylca... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Aromatic alcohol | Ester | null | null | c1c[nH]nc1.c1ccc2c(c1)CCCS2.C1CCCCC1 | HCl | C(Cl)Cl | null | null | CCn1ncc(C(=O)c2ccc3c(c2C)C(OC)CCS3(=O)=O)c1O.O=C(Cl)C1CCCCC1>C(Cl)Cl>CCn1ncc(C(=O)c2ccc3c(c2C)C(OC)CCS3(=O)=O)c1OC(=O)C1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7676d3f705f64b5888f4950efb2b2f22 | CCn1ncc(C(=O)c2ccc3c(c2C)C(=NOC)CCS3(=O)=O)c1O.O=C(CBr)c1ccccc1>>CCn1ncc(C(=O)c2ccc3c(c2C)C(=NOC)CCS3(=O)=O)c1OCC(=O)c1ccccc1 | CON=C1CCS(C2=CC=C(C(=C12)C)C(=O)C=1C=NN(C1O)CC)(=O)=O.N1N=CC=C1.C(C(=O)C1=CC=CC=C1)Br.C([O-])([O-])=O.[K+].[K+]>>CON=C1CCS(C2=CC=C(C(=C12)C)C(=O)C=1C=NN(C1OCC(=O)C1=CC=CC=C1)CC)(=O)=O | [CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH:11][c:12]3[c:13]([c:14]2[CH3:15])[C:16](=[N:17][O:18][CH3:19])[CH2:20][CH2:21][S:22]3(=[O:23])=[O:24])[c:25]1[OH:26].Br[CH2:27][C:28](=[O:29])[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1>>[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][cH... | CCn1ncc(C(=O)c2ccc3c(c2C)C(=NOC)CCS3(=O)=O)c1O.O=C(CBr)c1ccccc1 | CCn1ncc(C(=O)c2ccc3c(c2C)C(=NOC)CCS3(=O)=O)c1OCC(=O)c1ccccc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 8060b8e1565497a5ddf79be1adfe74f552b31798797b8841753247b06bdd2051 | 8749b179916f131d393264a24309227dc6177f560726bed2d1f4567dc2ac63f5 | N=C1CCS(=O)(=O)c2ccc(C(=O)c3cn[nH]c3OCC(=O)c3ccccc3)cc21 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[C:5]-[#7;a:6]1:[#7;a:7]:[c:8]:[c:9](-[C:10]=[O;D1;H0:11]):[c:12]:1-[OH;D1;+0:13]>>[C:5]-[#7;a:6]1:[#7;a:7]:[c:8]:[c:9](-[C:10]=[O;D1;H0:11]):[c:12]:1-[O;H0;D2;+0:13]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4] | 52 | [{"value": 52.0, "product": "CON=C1CCS(C2=CC=C(C(=C12)C)C(=O)C=1C=NN(C1OCC(=O)C1=CC=CC=C1)CC)(=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.4 Gram (1.1 mmol) of 4-methoxyimino-5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide corresponding to pyrazole derivative (I-H), 0.23 g (1.2 mmol) of phenacyl bromide corresponding to compound B-A-Hal and 0.15 g of potassium carbonate were added to 10 ml of acetone, and the mixture was stirre... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Aromatic alcohol | Ketone.Ether | null | null | c1c[nH]nc1.c1ccc2c(c1)CCCS2.c1ccccc1 | HBr | CC(=O)C | null | null | CCn1ncc(C(=O)c2ccc3c(c2C)C(=NOC)CCS3(=O)=O)c1O.O=C(CBr)c1ccccc1>CC(=O)C>CCn1ncc(C(=O)c2ccc3c(c2C)C(=NOC)CCS3(=O)=O)c1OCC(=O)c1ccccc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-c66dc862259d4aac940736920bae0111 | CCn1nccc1O.Cc1cc(C(=O)O)c(C)c2c1S(=O)(=O)CCC2(C)C>>CCn1ncc(C(=O)c2cc(C)c3c(c2C)C(C)(C)CCS3(=O)=O)c1O | CC1(CCS(C2=C(C=C(C(=C12)C)C(=O)O)C)(=O)=O)C.C1(CCCCC1)N=C=NC1CCCCC1.C(C)N1N=CC=C1O.OC1=CC=NN1.C([O-])([O-])=O.[K+].[K+].S1C(CCC2=CC=CC=C12)C(=O)O>>CC1(CCS(C2=C(C=C(C(=C12)C)C(=O)C=1C=NN(C1O)CC)C)(=O)=O)C | [CH3:1][CH2:2][n:3]1[n:4][cH:5][cH:6][c:25]1[OH:26].O[C:7](=[O:8])[c:9]1[cH:10][c:11]([CH3:12])[c:13]2[c:14]([c:15]1[CH3:16])[C:17]([CH3:18])([CH3:19])[CH2:20][CH2:21][S:22]2(=[O:23])=[O:24]>>[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][c:11]([CH3:12])[c:13]3[c:14]([c:15]2[CH3:16])[C:17]([CH3:18])([C... | CCn1nccc1O.Cc1cc(C(=O)O)c(C)c2c1S(=O)(=O)CCC2(C)C | CCn1ncc(C(=O)c2cc(C)c3c(c2C)C(C)(C)CCS3(=O)=O)c1O | null | null | C(C)(C)(CC)O | C-C Coupling | Friedel-Crafts acylation | a0eb501576cd1840858c4075b65e6179ed5aa7a8de808c0e168225f186f28b05 | a49756d2995b35bf1c4b6840928f031562470ef5bd676447fb43ce2575147daa | O=C(c1cn[nH]c1)c1ccc2c(c1)CCCS2(=O)=O | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[cH;D2;+0:10]:[c:11]:1-[O;D1;H1:12]>>[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c;H0;D3;+0:10](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:11]:1-[O;D1;H1:12] | 62.6 | [{"value": 62.0, "product": "CC1(CCS(C2=C(C=C(C(=C12)C)C(=O)C=1C=NN(C1O)CC)C)(=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.6, "product": "CC1(CCS(C2=C(C=C(C(=C12)C)C(=O)C=1C=NN(C1O)CC)C)(=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | 7.4 Grams (0.026 mol) of 4,4,5,8-tetramethylthiochroman-6-carboxylic acid-1,1-dioxide corresponding to thiochroman carboxylic acid (IIIc), 3.4 g (0.03 mol) of 1-ethyl-5-hydroxypyrazole corresponding to 5-hydroxypyrazole (II) and 6.22 g (0.03 mol) of DCC (N,N'-dicyclohexylcarbodiimide) were all together added to 50 ml o... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccn[nH]1 | c1c[nH]nc1 | c1c[nH]nc1.c1ccc2c(c1)CCCS2 | HO- | C(C)(C)(CC)O | null | 0.5 | CCn1nccc1O.Cc1cc(C(=O)O)c(C)c2c1S(=O)(=O)CCC2(C)C>C(C)(C)(CC)O>CCn1ncc(C(=O)c2cc(C)c3c(c2C)C(C)(C)CCS3(=O)=O)c1O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b437e05b173c435b946ece88305eb18d | CCS(=O)(=O)Cl.CCn1ncc(C(=O)c2cc(C)c3c(c2C)C(C)(C)CCS3(=O)=O)c1O>>CCn1ncc(C(=O)c2cc(C)c3c(c2C)C(C)(C)CCS3(=O)=O)c1OS(=O)(=O)CC | C(C)S(=O)(=O)Cl.C([O-])([O-])=O.[K+].[K+].CC1(CCS(C2=C(C=C(C(=C12)C)C(=O)C=1C=NN(C1O)CC)C)(=O)=O)C.N1N=CC=C1>>CC1(CCS(C2=C(C=C(C(=C12)C)C(=O)C=1C=NN(C1OS(=O)(=O)CC)CC)C)(=O)=O)C | Cl[S:27](=[O:28])(=[O:29])[CH2:30][CH3:31].[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][c:11]([CH3:12])[c:13]3[c:14]([c:15]2[CH3:16])[C:17]([CH3:18])([CH3:19])[CH2:20][CH2:21][S:22]3(=[O:23])=[O:24])[c:25]1[OH:26]>>[CH3:1][CH2:2][n:3]1[n:4][cH:5][c:6]([C:7](=[O:8])[c:9]2[cH:10][c:11]([CH3:12])[c:13]3... | CCS(=O)(=O)Cl.CCn1ncc(C(=O)c2cc(C)c3c(c2C)C(C)(C)CCS3(=O)=O)c1O | CCn1ncc(C(=O)c2cc(C)c3c(c2C)C(C)(C)CCS3(=O)=O)c1OS(=O)(=O)CC | null | [Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC | C(Cl)Cl.O | Acylation | Formation of Sulfonic Esters | 9339e107bef60affc137d23d580808fc37a7625dc676ebb48fe8271cd9670535 | 7ef9cdb7b67e90f0e8b5d9f8fed73f04903b09cd9fd8ced1da4341e88385cae2 | O=C(c1cn[nH]c1)c1ccc2c(c1)CCCS2(=O)=O | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C;D1;H3:5].[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10](-[C:11]=[O;D1;H0:12]):[c:13]:1-[OH;D1;+0:14]>>[C:6]-[#7;a:7]1:[#7;a:8]:[c:9]:[c:10](-[C:11]=[O;D1;H0:12]):[c:13]:1-[O;H0;D2;+0:14]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[C:4]-[C;D1;H3:5] | 82 | [{"value": 82.0, "product": "CC1(CCS(C2=C(C=C(C(=C12)C)C(=O)C=1C=NN(C1OS(=O)(=O)CC)CC)C)(=O)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.0, "product": "CC1(CCS(C2=C(C=C(C(=C12)C)C(=O)C=1C=NN(C1OS(=O)(=O)CC)CC)C)(=O)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 0.7 Gram (1.9 mmol) of the 4,4,5,8-tetramethyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide (Compound Ic-1) corresponding to pyrazole derivative (I-H), obtained in Referential Production Example 5, was dissolved in 8 ml of methylene chloride. Then, a solution of 0.51 g (3.8 mmol) of potassium carbon... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic alcohol.Sulfonyl halide | Sulfonate | null | null | c1c[nH]nc1.c1ccc2c(c1)CCCS2 | HCl | [Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC.C(Cl)Cl.O | null | null | CCS(=O)(=O)Cl.CCn1ncc(C(=O)c2cc(C)c3c(c2C)C(C)(C)CCS3(=O)=O)c1O>[Cl-].C(C1=CC=CC=C1)[N+](CC)(CC)CC.C(Cl)Cl.O>CCn1ncc(C(=O)c2cc(C)c3c(c2C)C(C)(C)CCS3(=O)=O)c1OS(=O)(=O)CC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aad0c6cdb96e435783b60b50f263f74c | COC(=O)[C@@H]1CN(Cc2ccccc2)C[C@H]1c1ccccc1OC>>COc1ccccc1[C@@H]1CN(Cc2ccccc2)C[C@H]1CO | [Cl-].[Na+].C(C)(C)O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C1=CC=CC=C1)N1C[C@H]([C@@H](C1)C1=C(C=CC=C1)OC)C(=O)OC>>C(C1=CC=CC=C1)N1C[C@H]([C@@H](C1)C1=C(C=CC=C1)OC)CO | CO[C:21]([C@H:20]1[C@H:9]([c:8]2[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][cH:7]2)[CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19]1)=[O:22]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[C@@H:9]1[CH2:10][N:11]([CH2:12][c:13]2[cH:14][cH:15][cH:16][cH:17][cH:18]2)[CH2:19][C@H:20]1[CH2:21][OH:22] | COC(=O)[C@@H]1CN(Cc2ccccc2)C[C@H]1c1ccccc1OC | COc1ccccc1[C@@H]1CN(Cc2ccccc2)C[C@H]1CO | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(CN2CC[C@H](c3ccccc3)C2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[C:5]-[#7:6]>>[#7:6]-[C:5]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:4] | null | [] | 5 | CELSIUS | 1 | HOUR | To 560 mmol of lithium aluminum hydride in 800 ml of tetrahydrofuran (THF), under a nitrogen atmosphere and at 5° C., are added 225 mmol of methyl [trans-1-benzyl-4-(2-methoxyphenyl)pyrrolidin-3-yl]carboxylate (described in Preparation A) dissolved in 500 ml of THF. After stirring for 1 hour at 5° C., 139 ml of isoprop... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.C1CC[NH]C1.c1ccccc1 | Other | O1CCCC1 | 5 | 1 | COC(=O)[C@@H]1CN(Cc2ccccc2)C[C@H]1c1ccccc1OC>O1CCCC1>COc1ccccc1[C@@H]1CN(Cc2ccccc2)C[C@H]1CO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7d193050015441f093d40bd7590a4914 | COc1ccc2c(c1)OC(=O)[C@H]1CN(Cc3ccccc3)C[C@@H]21>>COc1ccc([C@H]2CN(Cc3ccccc3)C[C@H]2CO)c(O)c1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].C(C1=CC=CC=C1)N1C[C@H]2[C@@H](C1)C1=C(OC2=O)C=C(C=C1)OC>>C(C1=CC=CC=C1)N1C[C@H]([C@H](C1)C1=C(C=C(C=C1)OC)O)CO | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:21]([cH:23]1)[O:22][C:19](=[O:20])[C@@H:18]1[C@H:7]2[CH2:8][N:9]([CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[CH2:17]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C@H:7]2[CH2:8][N:9]([CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[CH2:17][C@H:18]2[CH2:19][OH:20])[c:21]([OH:... | COc1ccc2c(c1)OC(=O)[C@H]1CN(Cc3ccccc3)C[C@@H]21 | COc1ccc([C@H]2CN(Cc3ccccc3)C[C@H]2CO)c(O)c1 | null | null | C1CCOC1 | Reduction | OtherReaction | ae8164954c34b21c8fa38773596af12d1e0783da323a81aa08ede45a74484775 | bb621eee13e64a87401761367bc299c7ba93ca9330953c6249ee208fbd91494f | c1ccc(CN2CC[C@@H](c3ccccc3)C2)cc1 | [#7:1]-[C:2]-[C:3]1-[C:4]-[c:5]:[c:6](:[c:7])-[O;H0;D2;+0:8]-[C;H0;D3;+0:9]-1=[O;H0;D1;+0:10]>>[#7:1]-[C:2]-[C:3](-[CH2;D2;+0:9]-[OH;D1;+0:10])-[C:4]-[c:5]:[c:6](-[OH;D1;+0:8]):[c:7] | null | [] | null | null | null | null | To 230 mmol of lithium aluminum hydride in 800 ml of THF, under a nitrogen atmosphere, are added 180 mmol of cis-2-benzyl-7-methoxy-1,3,3a,9b-tetrahydrobenzopyrano[3,4-c]pyrrol-4-one, described in Preparation G, at +5° C. The reaction medium is maintained at +10° C. for one hour before being hydrolyzed, and is filtered... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol.Aromatic alcohol | c1ccc2c(c1)OC[C@H]1C[NH]C[C@@H]21 | null | c1ccccc1.C1CC[NH]C1.c1ccccc1 | null | C1CCOC1 | null | null | COc1ccc2c(c1)OC(=O)[C@H]1CN(Cc3ccccc3)C[C@@H]21>C1CCOC1>COc1ccc([C@H]2CN(Cc3ccccc3)C[C@H]2CO)c(O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-a6aacc5162fa4403a0432cd2a4af49bf | CC(=O)C(C#N)c1ccc(NC(=O)OC(C)(C)C)cc1.CCOC(CNN)OCC>>Cc1nn2cc[nH]c2c1-c1ccc(N)cc1 | C(C)(C)(C)OC(=O)NC1=CC=C(C=C1)C(C#N)C(C)=O.C(C)O.C(C)OC(CNN)OCC.Cl>>Cl.NC1=CC=C(C=C1)C1=C2N(N=C1C)C=CN2 | CC(C)(C)OC(=O)[NH:14][c:13]1[cH:12][cH:11][c:10]([CH:9]([C:2](=O)[CH3:1])[C:8]#[N:7])[cH:16][cH:15]1.CCO[CH:6](OCC)[CH2:5][NH:4][NH2:3]>>[CH3:1][c:2]1[n:3][n:4]2[cH:5][cH:6][nH:7][c:8]2[c:9]1-[c:10]1[cH:11][cH:12][c:13]([NH2:14])[cH:15][cH:16]1 | CC(=O)C(C#N)c1ccc(NC(=O)OC(C)(C)C)cc1.CCOC(CNN)OCC | Cc1nn2cc[nH]c2c1-c1ccc(N)cc1 | null | null | C(C)(=O)OCC.O1CCOCC1 | Aromatic Heterocycle Formation | OtherReaction | 2c7bd0812528ed957fdd423e3bb9b0984f33ed133c2c2d218df2c9c73827ee41 | 7ede329335a326fd75937dd500b2b659716c73769382fa44998c1f4e3a815127 | c1ccc(-c2cnn3cc[nH]c23)cc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[CH;D3;+0:6](-[C;H0;D2;+0:7]#[N;H0;D1;+0:8])-[C;H0;D3;+0:9](=O)-[C;D1;H3:10]):[c:11]:[c:12]:1.C-C-O-[CH;D3;+0:13](-O-C-C)-[CH2;D2;+0:14]-[NH;D2;+0:15]-[NH2;D1;+0:16]>>[C;D1;H3:10]-[c;H0;D3;+0:9]1:[n;H0;D2;+0:16]:[n;H0;D3;+0:15]2:[cH;D2;+0:14]:[cH;D2;+0... | null | [] | null | null | null | null | A mixture of 2.5 g of 2-(4-t-butoxycarbonylaminophenyl)-3-oxobutyronitrile, 20 ml of ethanol and 1.4 g of 2,2-diethoxyethylhydrazine was heated under reflux for 2 hours. 20 ml of 4N hydrogen chloride in dioxane were added, and then the whole mixture was heated under reflux for a further 30 minutes. After the mixture ha... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Carbamic ester.Ketone.Ether.Ether.Ether.Nitrile.Boc | Primary amine | null | c1cn2[nH]ccc2n1 | c1cn2[nH]ccc2n1.c1ccccc1 | HO- | C(C)(=O)OCC.O1CCOCC1 | null | null | CC(=O)C(C#N)c1ccc(NC(=O)OC(C)(C)C)cc1.CCOC(CNN)OCC>C(C)(=O)OCC.O1CCOCC1>Cc1nn2cc[nH]c2c1-c1ccc(N)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7b357d5bf4334f0fb405475a558ece52 | O=S(=O)(Cl)Cl.c1ccc(COc2ccccc2)cc1>>O=S(=O)(Cl)c1ccc(OCc2ccccc2)cc1 | S(=O)(=O)(Cl)Cl.C1(=CC=CC=C1)OCC1=CC=CC=C1>>C(C1=CC=CC=C1)OC1=CC=C(C=C1)S(=O)(=O)Cl | Cl[S:2](=[O:1])(=[O:3])[Cl:4].[cH:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1>>[O:1]=[S:2](=[O:3])([Cl:4])[c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1 | O=S(=O)(Cl)Cl.c1ccc(COc2ccccc2)cc1 | O=S(=O)(Cl)c1ccc(OCc2ccccc2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 04bb0e110ac9bc3104a40572864ecdd042b39019cff0ea96d1a0ad7c9eb6ecf3 | d32b60b8f9bfd187c6c9f1eef6a22a00f53525a7532b83aba763d5389c9e4280 | c1ccc(COc2ccccc2)cc1 | Cl-[S;H0;D4;+0:1](-[Cl;D1;H0:2])(=[O;D1;H0:3])=[O;D1;H0:4].[c:5]:[c:6]:[cH;D2;+0:7]:[c:8]:[c:9]>>[Cl;D1;H0:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[c;H0;D3;+0:7](:[c:6]:[c:5]):[c:8]:[c:9] | null | [] | 90 | CELSIUS | 30 | MINUTE | A 1.12 portion of anhydrous DMF is cooled to 0° C. and treated dropwise with 2.06 g of sulfuryl chloride. The resulting suspension is stirred for 30 min., then treated with 1.50 g of benzyl phenyl ether. The mixture is heated at 90° C. for 3 h, then cooled, extracted with brine and methylene chloride, and dried over Mg... | 10.6084/m9.figshare.5104873.v1 | null | null | Sulfonyl halide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | CN(C)C=O | 90 | 0.5 | O=S(=O)(Cl)Cl.c1ccc(COc2ccccc2)cc1>CN(C)C=O>O=S(=O)(Cl)c1ccc(OCc2ccccc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f02b90c8e56b477c889ab251909baee4 | N.O=C(O)CC1CCCC1>>NC(=O)CC1CCCC1 | N.C1(CCCC1)CC(=O)O.S(=O)(Cl)Cl.CN(C)C=O>>C1(CCCC1)CC(=O)N | [NH3:1].O[C:2](=[O:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1>>[NH2:1][C:2](=[O:3])[CH2:4][CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9]1 | N.O=C(O)CC1CCCC1 | NC(=O)CC1CCCC1 | null | null | ClCCl | Acylation | Carboxylic acid to amide conversion | 1283aef55d7ee699f097a8e5267689198c76ba671644401547f902657820236d | cb0a71c3fb37a76e96fbd81aae6f95a28398a03d1ad2c8e877085e735efb98f1 | C1CCCC1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[NH3;D0;+0:5]>>[C:4]-[C:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2] | 52 | [{"value": 52.0, "product": "C1(CCCC1)CC(=O)N", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | Cyclopentylacetic acid (5.2 g, 41 mmol) and thionyl chloride (10 mL) were combined then DMF (0.2 mL) was added and the solution was stirred 1.5 h at R.T. Dichloromethane (10 mL) was added and the solution cooled in an ice bath whereupon 25% aqueous ammonia (30 mL) was added and the mixture stirred for 0.5 h. The soluti... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary amide | null | null | C1CCCC1 | HO- | ClCCl | null | 1.5 | N.O=C(O)CC1CCCC1>ClCCl>NC(=O)CC1CCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aad08f27e18e4070affc2570d3f9689b | BrCc1ccccc1.NC(=O)C1CCNCC1>>O=C(NCc1ccccc1)C1CCNCC1 | N1CCC(CC1)C(=O)N.C(C1=CC=CC=C1)Br>>C(C1=CC=CC=C1)NC(=O)C1CCNCC1 | Br[CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[O:1]=[C:2]([NH2:3])[CH:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[CH:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1 | BrCc1ccccc1.NC(=O)C1CCNCC1 | O=C(NCc1ccccc1)C1CCNCC1 | null | null | CS(=O)C.CCOC(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of primary amines with alkyl halides | 5a8ba8f657ca28e5102d919f34d9bdecf23bf3cdd14c1b5b58cfb8cd3076d18a | 66b130147811df95ca7554e5323dafaeff369902d2ef2b8f39832e5664e5e375 | O=C(NCc1ccccc1)C1CCNCC1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[NH2;D1;+0:7])=[O;D1;H0:8]>>[C:5]-[C:6](=[O;D1;H0:8])-[NH;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | 35 | [{"value": 35.0, "product": "C(C1=CC=CC=C1)NC(=O)C1CCNCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.7, "product": "C(C1=CC=CC=C1)NC(=O)C1CCNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Piperidinecarboxamide (10.2 g, 78.0 mmol) in DMSO (10 mL) was treated with benzyl bromide (20.0 mL, 168 mmol). The mixture was diluted with EtOAc and washed with 1N aq. HCl, 5N aq. NaOH, dried over MgSO4, and concentrated to give 5.90 g (35%) of N-benzyl-4-piperidinecarboxamide. [1H]-NMR(CDCl3) consistent with struct... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary amide | Secondary amide | null | null | c1ccccc1.C1CCNCC1 | HBr | CS(=O)C.CCOC(=O)C | null | null | BrCc1ccccc1.NC(=O)C1CCNCC1>CS(=O)C.CCOC(=O)C>O=C(NCc1ccccc1)C1CCNCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-554bd9dd465641989667d60605d8d5a8 | O=C(Cl)OCc1ccccc1.OC1CCNCC1>>O=C(OCc1ccccc1)N1CCCCC1 | OC1CCNCC1.CCN(CC)CC.ClC(=O)OCC1=CC=CC=C1.C(Cl)(Cl)Cl.CO>>C(=O)(OCC1=CC=CC=C1)N1CCCCC1 | Cl[C:2](=[O:1])[O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.O[CH:14]1[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1 | O=C(Cl)OCc1ccccc1.OC1CCNCC1 | O=C(OCc1ccccc1)N1CCCCC1 | null | null | C(Cl)Cl | Protection | OtherReaction | 542e05ffc7e3d0da44bf85ee5289c12b8172b2180d6c015ec758d6abffe9106c | 74a226a647253aaa75e7549a251233057634f1c7dbcbb9801acebcaa92e8b46d | O=C(OCc1ccccc1)N1CCCCC1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].O-[CH;D3;+0:5]1-[C:6]-[C:7]-[NH;D2;+0:8]-[C:9]-[C:10]-1>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:8]1-[C:7]-[C:6]-[CH2;D2;+0:5]-[C:10]-[C:9]-1 | 59.2 | [{"value": 55.0, "product": "C(=O)(OCC1=CC=CC=C1)N1CCCCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 59.2, "product": "C(=O)(OCC1=CC=CC=C1)N1CCCCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | 4-Hydroxypiperidine (10.8 g, 107 mmol) and Et3N (17 mL, 123 mmol) in 80 mL of CH2Cl2 was cooled in an ice bath whereupon benzyl chloroformate (16.3 mL, 114 mmol) was added. After stirring 1.5 h at R.T. the mixture was subjected to standard work-up conditions to give 13.9 g (55%) of N-Cbz-piperidine after chromatography... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Secondary alcohol.Secondary amine | Carbamic ester.Ether | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.C1CC[NH]CC1 | HCl | C(Cl)Cl | null | 1.5 | O=C(Cl)OCc1ccccc1.OC1CCNCC1>C(Cl)Cl>O=C(OCc1ccccc1)N1CCCCC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-d13c6a79a6d1480ca22e3b132fc186d6 | O=C(OCc1ccccc1)N1CCCCC1.O=C1NC(=O)c2ccccc21>>O=C(OCc1ccccc1)N1CCC(N2C(=O)c3ccccc3C2=O)CC1 | C1(C=2C(C(N1)=O)=CC=CC2)=O.C(=O)(OCC1=CC=CC=C1)N1CCCCC1.CCOC(=O)/N=N/C(=O)OCC.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)N1C(C=2C(C1=O)=CC=CC2)=O | [O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH2:14][CH2:26][CH2:27]1.[NH:15]1[C:16](=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[C:24]1=[O:25]>>[O:1]=[C:2]([O:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[N:11]1[CH2:12][CH2:13][CH:14]([N:15]2[C:16](=[O:17])[c:18]3[cH:... | O=C(OCc1ccccc1)N1CCCCC1.O=C1NC(=O)c2ccccc21 | O=C(OCc1ccccc1)N1CCC(N2C(=O)c3ccccc3C2=O)CC1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | OtherReaction | 8d961cc25bdf2bfb5e1b8ccc1c7515886b56ce7e26d872f1ef119f2be92c18d0 | 778765539b1f5c85e4df7554d2accb6652853c86a94bb67ba040cf186b3e9c48 | O=C(OCc1ccccc1)N1CCC(N2C(=O)c3ccccc3C2=O)CC1 | [#7:1]1-[C:2]-[C:3]-[CH2;D2;+0:4]-[C:5]-[C:6]-1.[O;D1;H0:7]=[C:8]1-[NH;D2;+0:9]-[C:10](=[O;D1;H0:11])-[c:12]:[c:13]-1>>[O;D1;H0:7]=[C:8]1-[c:13]:[c:12]-[C:10](=[O;D1;H0:11])-[N;H0;D3;+0:9]-1-[CH;D3;+0:4]1-[C:3]-[C:2]-[#7:1]-[C:6]-[C:5]-1 | 50 | [{"value": 50.0, "product": "C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)N1C(C=2C(C1=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 10.5 | HOUR | A solution of DEAD (1.61 mL, 10.2 mmol) in 20 mL of THF was added to a solution of triphenylphosphine (2.69 g, 10.3 mmol), the N-Cbz-piperidine prepared in Example 16A (2.36 g, 100 mmol) and phthalimide (1.50 g, 10.2 mmol) in 80 mL of THF. After stirring 10.5 h at R.T. the mixture was quenched with water, extracted wit... | 10.6084/m9.figshare.5104873.v1 | null | Unsubstituted dicarboximide | Substituted dicarboximide | C1CC[NH]CC1.c1ccc2c(c1)CNC2 | C1CC[NH]CC1.c1ccc2c(c1)C[NH]C2 | c1ccccc1.C1CC[NH]CC1.c1ccc2c(c1)C[NH]C2 | null | C1CCOC1 | null | 10.5 | O=C(OCc1ccccc1)N1CCCCC1.O=C1NC(=O)c2ccccc21>C1CCOC1>O=C(OCc1ccccc1)N1CCC(N2C(=O)c3ccccc3C2=O)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2cac9a20d7c04458add12877e56c0bdb | O=C(OCc1ccccc1)N1CCC(N2C(=O)c3ccccc3C2=O)CC1>>NC1CCN(C(=O)OCc2ccccc2)CC1 | C(=O)([O-])[O-].[K+].[K+].C(C1=CC=CC=C1)OC(=O)N1CCC(CC1)N1C(C=2C(C1=O)=CC=CC2)=O.O.NN>>NC1CCN(CC1)C(=O)OCC1=CC=CC=C1 | O=C1c2ccccc2C(=O)[N:1]1[CH:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1>>[NH2:1][CH:2]1[CH2:3][CH2:4][N:5]([C:6](=[O:7])[O:8][CH2:9][c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)[CH2:16][CH2:17]1 | O=C(OCc1ccccc1)N1CCC(N2C(=O)c3ccccc3C2=O)CC1 | NC1CCN(C(=O)OCc2ccccc2)CC1 | null | null | C(C)O.[Cl-].[Na+].O | Reduction | Phthalimide deprotection | d9f63cee80ef758bd939ff2a10772447b3092f1576180488281833a98eb1691a | dbfe4201a9328005dfaec4c3f363ddbb4ef3c9b825f648735dc97b2b57396333 | O=C(OCc1ccccc1)N1CCCCC1 | O=C1-[N;H0;D3;+0:1](-[C:2](-[C:3])-[C:4])-C(=O)-c2:c:c:c:c:c:2-1>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4] | 85 | [{"value": 85.0, "product": "NC1CCN(CC1)C(=O)OCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | 1-Benzyloxycarbonyl-4-phthalimidylpiperidine (1.50 g, 4.27 mmol), prepared in Example 16B, was taken up in 20 mL of ethanol. To this solution was added hydrazine monohydrate (35 mL, 700 mmol) and this mixture was heated at 100° C. for 3 h. Brine solution (40 mL) and 10% aq. K2CO3 (60 mL) were added and the mixture was ... | 10.6084/m9.figshare.5104873.v1 | null | Substituted dicarboximide | Primary amine | c1ccc2c(c1)C[NH]C2 | null | C1CC[NH]CC1.c1ccccc1 | HO- | C(C)O.[Cl-].[Na+].O | 100 | null | O=C(OCc1ccccc1)N1CCC(N2C(=O)c3ccccc3C2=O)CC1>C(C)O.[Cl-].[Na+].O>NC1CCN(C(=O)OCc2ccccc2)CC1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f19bba0b067b4f289e036aa25822eeb2 | CC(C)(C)Cl.CCCCCC.Oc1cccc(-c2ccccc2)c1>>CC(C)(C)c1ccc(-c2ccc(C(C)(C)C)c(O)c2)cc1 | CCCCCC.[Cl-].[Al+3].[Cl-].[Cl-].C1(=CC=CC=C1)C=1C=C(C=CC1)O.C(C)(C)(C)Cl.C(Cl)Cl>>C(C)(C)(C)C1=C(C=C(C=C1)C1=CC=C(C=C1)C(C)(C)C)O | Cl[C:13]([CH3:14])([CH3:15])[CH3:16].C(C[CH2:4]C[CH3:3])[CH3:1].[cH:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][cH:12][c:17]([OH:18])[cH:19]2)[cH:20][cH:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[c:5]1[cH:6][cH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([C:13]([CH3:14])([CH3:15])[CH3:16])[c:17]([OH:18])[cH:19]2)[cH:20][cH:21]1 | CC(C)(C)Cl.CCCCCC.Oc1cccc(-c2ccccc2)c1 | CC(C)(C)c1ccc(-c2ccc(C(C)(C)C)c(O)c2)cc1 | null | null | null | C-C Coupling | OtherReaction | e2d91cd51c75cd6fe43798b97f7e7a27025911ff838a15bd177f1e64c8731bbd | 28f7fcf0a1b08f7b5dc0f15b864f88b253059b1992ba5d9af160bb6fe1bd3f6a | c1ccc(-c2ccccc2)cc1 | Cl-[C;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C;D1;H3:4].[CH3;D1;+0:5]-C-C-[CH2;D2;+0:6]-C-[CH3;D1;+0:7].[O;D1;H1:8]-[c:9](:[c:10]):[cH;D2;+0:11]:[c:12]:[c:13].[c:14]:[c:15]:[cH;D2;+0:16]:[c:17]:[c:18]>>[C;D1;H3:2]-[C;H0;D4;+0:1](-[C;D1;H3:3])(-[C;D1;H3:4])-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:9](-[O;D1;H1:8]):[c:10].[C... | null | [] | null | null | 12 | HOUR | A suspension of 0.8 aluminum chloride in 50 mL of anhydrous methylene choloride is stirred under an anhydrous nitrogen atmosphere at 5°-15° C. while a solution of 17 g of 3-phenylphenol and 24 mL of t-butylchloride in 50 mL of anhydrous methylene chloride is added dropwise. The resultant mixture is stirred for 2 hours,... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide | null | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | null | null | 12 | CC(C)(C)Cl.CCCCCC.Oc1cccc(-c2ccccc2)c1>>CC(C)(C)c1ccc(-c2ccc(C(C)(C)C)c(O)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-64836a6fca744252ac2345f2b4e4762d | ClCCN1CCCC1.Oc1ccc(Oc2ccccc2)cc1>>c1ccc(Oc2ccc(OCCN3CCCC3)cc2)cc1 | O(C1=CC=CC=C1)C1=CC=C(C=C1)O.Cl.ClCCN1CCCC1.CCOCC.O>>O(C1=CC=CC=C1)C1=CC=C(OCCN2CCCC2)C=C1 | Cl[CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1.[cH:1]1[cH:2][cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([OH:10])[cH:18][cH:19]2)[cH:20][cH:21]1>>[cH:1]1[cH:2][cH:3][c:4]([O:5][c:6]2[cH:7][cH:8][c:9]([O:10][CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[cH:18][cH:19]2)[cH:20][cH:21]1 | ClCCN1CCCC1.Oc1ccc(Oc2ccccc2)cc1 | c1ccc(Oc2ccc(OCCN3CCCC3)cc2)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 7e1040116e3a4cf0e8ec5cc7865388d9cd0efabce6d320a1c25a36e411018d8b | d5f4610d46ccc0478471c5bc0fb862644eaf764bbc5d93badb39d54f6ec8e0a5 | c1ccc(Oc2ccc(OCCN3CCCC3)cc2)cc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#7:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[#7:3]-[C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | 92.9 | [{"value": 92.9, "product": "O(C1=CC=CC=C1)C1=CC=C(OCCN2CCCC2)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | A solution of 4-phenoxyphenol (0.56 g, 3.0 mmol), 1-(2-chloroethyl)-pyrrolidine HCl (0.51 g, 3.0 mmol) and powdered K2 CO3 (1.2 g, 8.7 mmol) in 30 mL DMF was stirred at 80°-90° C. for 15 hours. The solution was cooled, poured into Et2O and water and the ether layer washed with water and brine, dried over Na2SO4 and con... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aromatic alcohol | Ether | null | null | c1ccccc1.c1ccccc1.C1CC[NH]C1 | HCl | CN(C)C=O | null | 15 | ClCCN1CCCC1.Oc1ccc(Oc2ccccc2)cc1>CN(C)C=O>c1ccc(Oc2ccc(OCCN3CCCC3)cc2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-33cc46ae4b86423a92b024e4bd6cb9eb | CCOC(=O)C(=O)[O-].COc1cccc(OC)c1C(C)=O.C[O-]>>COC(=O)C(=O)C=C([O-])c1c(OC)cccc1OC | [Na].C(C)(C)OC(C)C.CC(=O)C1=C(C=CC=C1OC)OC.C(C(=O)[O-])(=O)OCC.C[O-].[Na+]>>[Na+].COC1=C(C(=CC=C1)OC)C(=CC(C(=O)OC)=O)[O-] | CCO[C:3](=[O:4])[C:5]([O-])=[O:6].[CH3:7][C:8](=[O:9])[c:10]1[c:11]([O:12][CH3:13])[cH:14][cH:15][cH:16][c:17]1[O:18][CH3:19].[CH3:1][O-:2]>>[CH3:1][O:2][C:3](=[O:4])[C:5](=[O:6])[CH:7]=[C:8]([O-:9])[c:10]1[c:11]([O:12][CH3:13])[cH:14][cH:15][cH:16][c:17]1[O:18][CH3:19] | CCOC(=O)C(=O)[O-].COc1cccc(OC)c1C(C)=O.C[O-] | COC(=O)C(=O)C=C([O-])c1c(OC)cccc1OC | null | null | CO | C-C Coupling | OtherReaction | 861d1140c1bf14edca2498b7091b2efd686a7dfdc1455a4210d69227711f7cf1 | 94c7364692188ef8ef531518cf74a9fca9728a2aa5d4b3e96a01bb7b82219171 | c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](-[O-])=[O;D1;H0:4].[C;D1;H3:5]-[O-;H0;D1:6].[CH3;D1;+0:7]-[C;H0;D3;+0:8](=[O;H0;D1;+0:9])-[c:10](:[c:11]):[c:12]>>[C;D1;H3:5]-[O;H0;D2;+0:6]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=[O;D1;H0:4])-[CH;D2;+0:7]=[C;H0;D3;+0:8](-[O-;H0;D1:9])-[c:10](:[c:11]):[c:12] | null | [] | null | null | 8 | HOUR | A solution of 100 g of 2,6-dimethoxyacetophenone and 7.5 ml of ethyl oxalate in 520 ml of anhydrous MeOH is added slowly to a solution of sodium methylate prepared from 12.7 g of sodium and 285 ml of anhydrous MeOH. The reaction mixture is heated to reflux for 7 hours and left overnight at RT. It is poured into 2 litre... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | Ketone.Ester | null | null | c1ccccc1 | HO- | CO | null | 8 | CCOC(=O)C(=O)[O-].COc1cccc(OC)c1C(C)=O.C[O-]>CO>COC(=O)C(=O)C=C([O-])c1c(OC)cccc1OC |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-7bfae8fa5eb84c9b9f50ce2960b99ca7 | Nc1ccc(C(=O)O)c2c1CCCC2>>Cl.NNc1ccc(C(=O)O)c2c1CCCC2 | N(=O)[O-].[Na+].Cl[Sn]Cl.NC1=CC=C(C=2CCCCC12)C(=O)O>>Cl.N(N)C1=CC=C(C=2CCCCC12)C(=O)O | [NH2:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[c:11]2[c:12]1[CH2:13][CH2:14][CH2:15][CH2:16]2>>[ClH:1].[NH2:2][NH:3][c:4]1[cH:5][cH:6][c:7]([C:8](=[O:9])[OH:10])[c:11]2[c:12]1[CH2:13][CH2:14][CH2:15][CH2:16]2 | Nc1ccc(C(=O)O)c2c1CCCC2 | Cl.NNc1ccc(C(=O)O)c2c1CCCC2 | null | null | Cl.O | Miscellaneous | OtherReaction | c4079cd46dafde13b56adeac363106820ab4184dee8b1ca632594de2bba804bd | 5c8e4e590249a630a16b10bd7a77b27600fffbea367a0b585a920dd877e5471b | c1ccc2c(c1)CCCC2 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[N;D1;H2:5]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 73.3 | [{"value": 73.3, "product": "Cl.N(N)C1=CC=C(C=2CCCCC12)C(=O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | null | null | A solution of 0.26 g of NaNO2 in 1 ml of water is added to a solution, cooled to -5° C., of 0.73 g of 4-amino-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid in 10 ml of concentrated HCl. After one and a half hours of stirring at -5° C., a solution of 3.4 g of SnCl2 ·2H2O in 34 ml of concentrated HCl is added at -5° C.... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Hydrazine | null | null | c1ccc2c(c1)CCCC2 | Other | Cl.O | -5 | null | Nc1ccc(C(=O)O)c2c1CCCC2>Cl.O>Cl.NNc1ccc(C(=O)O)c2c1CCCC2 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-70a25d6a367f495c9c26f59a04ae0cc2 | Cc1c(N)ccc(C(=O)O)c1C>>Cc1c(NN)ccc(C(=O)O)c1C.Cl | N(=O)[O-].[Na+].Cl[Sn]Cl.NC1=C(C(=C(C(=O)O)C=C1)C)C>>Cl.CC1=C(C(=O)O)C=CC(=C1C)NN | [CH3:1][c:2]1[c:3]([NH2:4])[cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12]1[CH3:13]>>[CH3:1][c:2]1[c:3]([NH:4][NH2:5])[cH:6][cH:7][c:8]([C:9](=[O:10])[OH:11])[c:12]1[CH3:13].[ClH:14] | Cc1c(N)ccc(C(=O)O)c1C | Cc1c(NN)ccc(C(=O)O)c1C.Cl | null | null | Cl.O | Miscellaneous | OtherReaction | c4079cd46dafde13b56adeac363106820ab4184dee8b1ca632594de2bba804bd | 5c8e4e590249a630a16b10bd7a77b27600fffbea367a0b585a920dd877e5471b | c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[N;D1;H2:5]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 93.7 | [{"value": 93.7, "product": "Cl.CC1=C(C(=O)O)C=CC(=C1C)NN", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -5 | CELSIUS | 2 | HOUR | A solution of 1.87 g of NaNO2 in 7 ml of water is added slowly to a solution, cooled to -5° C., of 4.5 g of 4-amino-2,3-dimethylbenzoic acid in 135 ml of concentrated HCl. After 2 hours of stirring at -5° C., a solution of 25 g of SnCl2 ·2H2O in 250 ml of concentrated HCl is added at -10° C., and the mixture is stirred... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Hydrazine | null | null | c1ccccc1 | Other | Cl.O | -5 | 2 | Cc1c(N)ccc(C(=O)O)c1C>Cl.O>Cc1c(NN)ccc(C(=O)O)c1C.Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b8001a84916e479bb360b2e627d79199 | COc1cc(C(=O)O)ccc1N>>COc1cc(C(=O)O)ccc1NN.Cl | Cl[Sn]Cl.N(=O)[O-].[Na+].NC1=C(C=C(C(=O)O)C=C1)OC>>Cl.N(N)C1=C(C=C(C(=O)O)C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][cH:10][c:11]1[NH2:12]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][cH:10][c:11]1[NH:12][NH2:13].[ClH:14] | COc1cc(C(=O)O)ccc1N | COc1cc(C(=O)O)ccc1NN.Cl | null | null | Cl.O | Miscellaneous | OtherReaction | c4079cd46dafde13b56adeac363106820ab4184dee8b1ca632594de2bba804bd | 5c8e4e590249a630a16b10bd7a77b27600fffbea367a0b585a920dd877e5471b | c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[N;D1;H2:5]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 0 | CELSIUS | 15 | MINUTE | A solution of 2.17 g of NaNO2 in 40 ml of H2O is added slowly to a solution, cooled to 0° C., of 5 g of 4-amino-3-methoxybenzoic acid in 50 ml of concentrated HCl. After 1 hour 15 minutes of stirring at 0° C., the mixture is cooled to -10° C., and a solution of 23.6 g of SnCl2 ·2H2O in 20 ml of concentrated HCl and 20 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Hydrazine | null | null | c1ccccc1 | Other | Cl.O | 0 | 0.25 | COc1cc(C(=O)O)ccc1N>Cl.O>COc1cc(C(=O)O)ccc1NN.Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-951984be58214825afaa7f028775b4b9 | N#Cc1ccc(N)cc1Cl>>Cl.N#Cc1ccc(NN)cc1Cl | NC1=CC(=C(C#N)C=C1)Cl.Cl[Sn]Cl.N(=O)[O-].[Na+]>>Cl.ClC1=C(C#N)C=CC(=C1)NN | [N:2]#[C:3][c:4]1[cH:5][cH:6][c:7]([NH2:8])[cH:10][c:11]1[Cl:12]>>[ClH:1].[N:2]#[C:3][c:4]1[cH:5][cH:6][c:7]([NH:8][NH2:9])[cH:10][c:11]1[Cl:12] | N#Cc1ccc(N)cc1Cl | Cl.N#Cc1ccc(NN)cc1Cl | null | null | C1CCOC1.O.Cl | Miscellaneous | OtherReaction | c4079cd46dafde13b56adeac363106820ab4184dee8b1ca632594de2bba804bd | 5c8e4e590249a630a16b10bd7a77b27600fffbea367a0b585a920dd877e5471b | c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[N;D1;H2:5]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | -5 | CELSIUS | 2 | HOUR | 5 g of 4-amino-2-chlorobenzonitrile and 40 ml of concentrated HCl in 30 ml of THF are mixed at -5° C.; 2.26 g of NaNO2 in 30 ml of water are added and the mixture is left stirring for 2 hours, 30 g of SnCl2 ·2H2O in 30 ml of concentrated HCl are then added and stirring is maintained at -5° C. for 30 minutes.
Conditions... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Hydrazine | null | null | c1ccccc1 | Other | C1CCOC1.O.Cl | -5 | 2 | N#Cc1ccc(N)cc1Cl>C1CCOC1.O.Cl>Cl.N#Cc1ccc(NN)cc1Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-b9463e90fa6b413699ae9fcde2e663de | Nc1ccc(Cl)c(C(=O)O)c1>>Cl.NNc1ccc(Cl)c(C(=O)O)c1 | Cl[Sn]Cl.N(=O)[O-].[Na+].NC=1C=CC(=C(C(=O)O)C1)Cl>>Cl.N(N)C=1C=CC(=C(C(=O)O)C1)Cl | [NH2:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[c:9]([C:10](=[O:11])[OH:12])[cH:13]1>>[ClH:1].[NH2:2][NH:3][c:4]1[cH:5][cH:6][c:7]([Cl:8])[c:9]([C:10](=[O:11])[OH:12])[cH:13]1 | Nc1ccc(Cl)c(C(=O)O)c1 | Cl.NNc1ccc(Cl)c(C(=O)O)c1 | null | null | Cl.O | Miscellaneous | OtherReaction | c4079cd46dafde13b56adeac363106820ab4184dee8b1ca632594de2bba804bd | 5c8e4e590249a630a16b10bd7a77b27600fffbea367a0b585a920dd877e5471b | c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[N;D1;H2:5]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 123.1 | [{"value": 123.1, "product": "Cl.N(N)C=1C=CC(=C(C(=O)O)C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -3 | CELSIUS | 2 | HOUR | A solution of 2.11 g of NaNO2 in 40 ml of water is added over 30 minutes to a suspension, cooled to -2° C., of 5 g of 5-amino-2-chlorobenzoic acid in 50 ml of concentrated HCl. The solution is stirred for 2 hours at -3° C. and cooled to -10° C., and a solution of 23 g of SnCl2 ·2H2O in 20 ml of concentrated HCl and 20 ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Hydrazine | null | null | c1ccccc1 | Other | Cl.O | -3 | 2 | Nc1ccc(Cl)c(C(=O)O)c1>Cl.O>Cl.NNc1ccc(Cl)c(C(=O)O)c1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-e46e69b904a7491db50b6afa5f24b6f5 | Cc1ccc(C(=O)O)cc1N>>Cc1ccc(C(=O)O)cc1NN.Cl | N(=O)[O-].[Na+].Cl[Sn]Cl.NC=1C=C(C(=O)O)C=CC1C>>Cl.N(N)C=1C=C(C(=O)O)C=CC1C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][c:10]1[NH2:11]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][c:10]1[NH:11][NH2:12].[ClH:13] | Cc1ccc(C(=O)O)cc1N | Cc1ccc(C(=O)O)cc1NN.Cl | null | null | Cl.O.CC(=O)O | Miscellaneous | OtherReaction | c4079cd46dafde13b56adeac363106820ab4184dee8b1ca632594de2bba804bd | 5c8e4e590249a630a16b10bd7a77b27600fffbea367a0b585a920dd877e5471b | c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[N;D1;H2:5]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 0 | CELSIUS | 20 | MINUTE | A solution of 2.74 g of NaNO2 in 28 ml of water is added over 30 minutes to a solution, cooled to -5° C., of 5 g of 3-amino-4-methylbenzoic acid in 120 ml of concentrated HCl and 40 ml AcOH, and the mixture is left stirring for 1 hour 20 minutes at 0° C. After cooling to -10° C., a solution of 27.6 g of SnCl2 ·2H2O in ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Hydrazine | null | null | c1ccccc1 | Other | Cl.O.CC(=O)O | 0 | 0.333333 | Cc1ccc(C(=O)O)cc1N>Cl.O.CC(=O)O>Cc1ccc(C(=O)O)cc1NN.Cl |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-58c913b2ad0b45c7913c1bbe8dd60541 | Cc1cc([N+](=O)[O-])ccc1F.NN>>Cc1cc([N+](=O)[O-])ccc1NN.F | FC1=C(C=C(C=C1)[N+](=O)[O-])C.O.NN.O.NN>>F.N(N)C1=C(C=C(C=C1)[N+](=O)[O-])C | [CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][cH:9][c:10]1[F:13].[NH2:11][NH2:12]>>[CH3:1][c:2]1[cH:3][c:4]([N+:5](=[O:6])[O-:7])[cH:8][cH:9][c:10]1[NH:11][NH2:12].[FH:13] | Cc1cc([N+](=O)[O-])ccc1F.NN | Cc1cc([N+](=O)[O-])ccc1NN.F | null | null | CC(C)O | Heteroatom Alkylation and Arylation | OtherReaction | d8df4273e702dfa5f61e1fc063d26292e73a06b19b988689234fbb3a4a4eddc6 | 61806bbf8bb8981e140ee503663af0ef0e69dc4f34f6582f974a2e4218f7da88 | c1ccccc1 | [C;D1;H3:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[F;H0;D1;+0:5]):[c:6]:[c:7].[N;D1;H2:8]-[NH2;D1;+0:9]>>[C;D1;H3:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[NH;D2;+0:9]-[N;D1;H2:8]):[c:6]:[c:7].[FH;D0;+0:5] | null | [] | null | null | 2 | HOUR | A mixture of 4.6 g of 1-fluoro-2-methyl-4-nitrobenzene and 3 ml of hydrazine hydrate in 45 ml of 2-propanol is heated to reflux for 2 hours. 3 ml of hydrazine hydrate are added, refluxing is continued for 2 hours and the mixture is left overnight with stirring at RT. The precipitate formed is drained. 3.53 g of the exp... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aromatic halide | Hydrazine | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | CC(C)O | null | 2 | Cc1cc([N+](=O)[O-])ccc1F.NN>CC(C)O>Cc1cc([N+](=O)[O-])ccc1NN.F |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-bc7a243f2c2a4644a13ff947f64b4644 | BrBr.CC(C)[CH2][Mg][Cl].Cc1ccc(S(=O)(=O)Nc2ccc([N+](=O)[O-])cc2)cc1>>Br.Cc1ccc(S(=O)(=O)Nc2ccc(NN)c(CC(C)C)c2)cc1 | BrBr.[N+](=O)([O-])C1=CC=C(C=C1)NS(=O)(=O)C1=CC=C(C=C1)C.C(C(C)C)[Mg]Cl.C(C)N(CC)CC>>Br.N(N)C1=C(C=C(C=C1)NS(=O)(=O)C1=CC=C(C=C1)C)CC(C)C | Br[Br:1].[Cl][Mg][CH2:18][CH:19]([CH3:20])[CH3:21].O=[N+:15]([O-])[c:14]1[cH:13][cH:12][c:11]([NH:10][S:7]([c:6]2[cH:5][cH:4][c:3]([CH3:2])[cH:24][cH:23]2)(=[O:8])=[O:9])[cH:22][cH:17]1>>[BrH:1].[CH3:2][c:3]1[cH:4][cH:5][c:6]([S:7](=[O:8])(=[O:9])[NH:10][c:11]2[cH:12][cH:13][c:14]([NH:15][NH2:16])[c:17]([CH2:18][CH:19]... | BrBr.CC(C)[CH2][Mg][Cl].Cc1ccc(S(=O)(=O)Nc2ccc([N+](=O)[O-])cc2)cc1 | Br.Cc1ccc(S(=O)(=O)Nc2ccc(NN)c(CC(C)C)c2)cc1 | null | null | C1CCOC1.CCOCC | Functional Group Interconversion | OtherReaction | dd236e39b4ae6ec72e04aaa2773b4bd49b05f22bf8d330650412a2acdfc10051 | dd0956e7dcc59282d16a0d1fb44fe3474a77789c64febe0eded8eca82cfbe957 | O=S(=O)(Nc1ccccc1)c1ccccc1 | Br-[Br;H0;D1;+0:1].O=[N+;H0;D3:2](-[O-])-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7].[C;D1;H3:8]-[C:9](-[C;D1;H3:10])-[CH2;D2;+0:11]-[Mg]-[Cl]>>[BrH;D0;+0:1].[C;D1;H3:8]-[C:9](-[C;D1;H3:10])-[CH2;D2;+0:11]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3](-[NH;D2;+0:2]-[N;D1;H2:12]):[c:4] | null | [] | null | null | null | null | This compound is prepared according to the procedure described in step A of Preparation 2.18, from 10 g of N-(4-nitrophenyl)-4-methylbenzenesulphonamide in 100 ml of THF and 42.6 ml of a 2M solution of isobutylmagnesium chloride in ether, followed by 4.4 ml of bromine and 23.4 ml of triethylamine. 5.9 g of the expected... | 10.6084/m9.figshare.5104873.v1 | null | Magnesium halide.Nitro group | Hydrazine | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | Br-.Mg | C1CCOC1.CCOCC | null | null | BrBr.CC(C)[CH2][Mg][Cl].Cc1ccc(S(=O)(=O)Nc2ccc([N+](=O)[O-])cc2)cc1>C1CCOC1.CCOCC>Br.Cc1ccc(S(=O)(=O)Nc2ccc(NN)c(CC(C)C)c2)cc1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-5fccfb36b4f847b99c3306f4dc04bee7 | C=COC(C)=O.[OH-]>>C=CO.C=COC(C)=O | [OH-].[NH4+].C(C)(=O)OC=C>>C(=C)O.C(C)(=O)OC=C | [CH2:1]=[CH:5][O:6][C:7]([CH3:8])=[O:9].[OH-:3]>>[CH2:1]=[CH:2][OH:3].[CH2:4]=[CH:5][O:6][C:7]([CH3:8])=[O:9] | C=COC(C)=O.[OH-] | C=CO.C=COC(C)=O | null | null | CO | Acylation | OtherReaction | 8fe8083200843fe946bd12d67f4539032f043e35767053427736ef49982c73c5 | 25480c74bd02fabbbc377956ab30f65d8b71b4149771a58ac14cfcbe165b3d67 | null | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[CH;D2;+0:5]=[CH2;D1;+0:6].[OH-;D0:7]>>[C;D1;H2:8]=[CH;D2;+0:5]-[#8:4]-[C:2](-[C;D1;H3:1])=[O;D1;H0:3].[CH2;D1;+0:6]=[C:9]-[OH;D1;+0:7] | null | [] | null | null | null | null | This Example shows the preparation of high TFE content copolymer. The conditions of Example III were repeated except that a total of 470 mg of APS was added, the TFE addition rate was 0.01 lb/min (4.5 g/min), the vinyl acetate addition rate was 2 ml/min., and the final agitation rate was 80 rpm. 2580 g of a 25.0 wt % s... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Vinyl | Ester.Enol.Vinyl.Vinyl | null | null | null | null | CO | null | null | C=COC(C)=O.[OH-]>CO>C=CO.C=COC(C)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-f21f4d3aa1ac4453b3a2e9187d4eff8f | C=COC(C)=O.[OH-]>>C=CO.C=COC(C)=O | [OH-].[NH4+].C(C)(=O)OC=C>>C(C)(=O)OC=C.C(=C)O | [CH2:1]=[CH:5][O:6][C:7]([CH3:8])=[O:9].[OH-:3]>>[CH2:1]=[CH:2][OH:3].[CH2:4]=[CH:5][O:6][C:7]([CH3:8])=[O:9] | C=COC(C)=O.[OH-] | C=CO.C=COC(C)=O | null | null | CO | Acylation | OtherReaction | 8fe8083200843fe946bd12d67f4539032f043e35767053427736ef49982c73c5 | 25480c74bd02fabbbc377956ab30f65d8b71b4149771a58ac14cfcbe165b3d67 | null | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[CH;D2;+0:5]=[CH2;D1;+0:6].[OH-;D0:7]>>[C;D1;H2:8]=[CH;D2;+0:5]-[#8:4]-[C:2](-[C;D1;H3:1])=[O;D1;H0:3].[CH2;D1;+0:6]=[C:9]-[OH;D1;+0:7] | null | [] | null | null | 3 | DAY | To 100 g of a copolymer made by the process of the present invention and having the composition 55.8 wt % vinyl acetate, 32.8 wt % TFE and 11.4 wt % HFP, was added 500 ml of methanol and 40 ml of concentrated ammonium hydroxide to form a copolymer suspension in the methanol. After three days at room temperature with oc... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Vinyl | Ester.Enol.Vinyl.Vinyl | null | null | null | null | CO | null | 72 | C=COC(C)=O.[OH-]>CO>C=CO.C=COC(C)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-daa2e4e30ef942c09a4a540a3956b1ac | CCOC(C)=O.[OH-]>>C=CO.C=COC(C)=O | C(C)(=O)OCC.[OH-].[NH4+]>>C(C)(=O)OC=C.C(=C)O | [CH3:1][CH2:5][O:6][C:7]([CH3:8])=[O:9].[OH-:3]>>[CH2:1]=[CH:2][OH:3].[CH2:4]=[CH:5][O:6][C:7]([CH3:8])=[O:9] | CCOC(C)=O.[OH-] | C=CO.C=COC(C)=O | null | null | O | Acylation | OtherReaction | cb44b424e817a9ed1cecc5c7cb18abf82d23c8211a930d4bfe964096353ae852 | 10b0f728833e7c5aa84c06f83a2b8dc37d2805b80d07363861bfa14f6aaae5c9 | null | [C;D1;H3:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[CH2;D2;+0:5]-[CH3;D1;+0:6].[OH-;D0:7]>>[C;D1;H2:8]=[CH;D2;+0:5]-[#8:4]-[C:2](-[C;D1;H3:1])=[O;D1;H0:3].[CH2;D1;+0:6]=[C:9]-[OH;D1;+0:7] | null | [] | null | null | 2 | DAY | To 100 g of the same copolymer was added 1500 ml of ethyl acetate, 40 ml of concentrated ammonium hydroxide and 40 ml of water. After two days with stirring, the polymer dissolved to give a gel. During the next three weeks at room temperature, a progressive decrease in viscosity of the solution was noted. At this time ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ester.Enol.Vinyl.Vinyl | null | null | null | null | O | null | 48 | CCOC(C)=O.[OH-]>O>C=CO.C=COC(C)=O |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-9598dbc5228f4c2bae79065911c76e2b | CCCCCCC(O)CCCCCCCCCCC(=O)OC>>CCCCCCC(O)CCCCCCCCCCCO | [H-].[H-].[H-].[H-].[Li+].[Al+3].OC(CCCCCCCCCCC(=O)OC)CCCCCC.[OH-].[K+]>>C(CCCCCCCCCCC(CCCCCC)O)O | CO[C:19]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[OH:8])=[O:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([OH:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20] | CCCCCCC(O)CCCCCCCCCCC(=O)OC | CCCCCCC(O)CCCCCCCCCCCO | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | null | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3]-[C:4]>>[C:4]-[C:3]-[CH2;D2;+0:1]-[OH;D1;+0:2] | 86.6 | [{"value": 86.6, "product": "C(CCCCCCCCCCC(CCCCCC)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.4, "product": "C(CCCCCCCCCCC(CCCCCC)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A 5-liter flask equipped with a stirrer, dropping funnel and reflux tube was charged with 28.5 g (0.75 mol) of LiAlH4 and 2 liters of tetrahydrofuran, to which a solution of 237.0 g (0.75 mol) of methyl 12-hydroxyoctadecanate in 1 liter of tetrahydrofuran was added dropwise over 5 hours with stirring. After completion ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | null | Other | O1CCCC1 | null | 1 | CCCCCCC(O)CCCCCCCCCCC(=O)OC>O1CCCC1>CCCCCCC(O)CCCCCCCCCCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-0aef768b43124d028d286302e483b8f7 | CCCCCCC(O)CCCCCCCCCCCOCC1CO1.NCCO>>CCCCCCC(O)CCCCCCCCCCCOCC(O)CNCCO | C(O)CN.C(C1CO1)OCCCCCCCCCCCC(CCCCCC)O>>OCCNCC(COCCCCCCCCCCCC(CCCCCC)O)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([OH:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH:22]1[O:23][CH2:24]1.[NH2:25][CH2:26][CH2:27][OH:28]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]([OH:8])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH... | CCCCCCC(O)CCCCCCCCCCCOCC1CO1.NCCO | CCCCCCC(O)CCCCCCCCCCCOCC(O)CNCCO | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | null | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:4]-[C:5](-[OH;D1;+0:7])-[CH2;D2;+0:6]-[NH;D2;+0:3]-[C:2]-[C:1] | 77 | [{"value": 77.0, "product": "OCCNCC(COCCCCCCCCCCCC(CCCCCC)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 76.3, "product": "OCCNCC(COCCCCCCCCCCCC(CCCCCC)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A 200-ml flask equipped with a stirrer, reflux condenser and dropping funnel was charged with 35.0 g (0.57 mol) of ethanolamine and 35 g of ethanol, and the mixture was heated to 80° C. with stirring in a nitrogen atmosphere. To this mixture, 13.0 g (38 mmol) of 12-hydroxyoctadecyl glycidyl ether were added dropwise ov... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | null | null | C(C)O | 80 | null | CCCCCCC(O)CCCCCCCCCCCOCC1CO1.NCCO>C(C)O>CCCCCCC(O)CCCCCCCCCCCOCC(O)CNCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ab17bb46863940638ad69df37ccf3c23 | CCCCCCCCCCCCCCCCC(O)COCC1CO1.NCCO>>CCCCCCCCCCCCCCCCC(O)COCC(O)CNCCO | C(C1CO1)OCC(CCCCCCCCCCCCCCCC)O.C(O)CN>>OCCNCC(COCC(CCCCCCCCCCCCCCCC)O)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([OH:18])[CH2:19][O:20][CH2:21][CH:22]1[O:23][CH2:24]1.[NH2:25][CH2:26][CH2:27][OH:28]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH... | CCCCCCCCCCCCCCCCC(O)COCC1CO1.NCCO | CCCCCCCCCCCCCCCCC(O)COCC(O)CNCCO | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | null | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:4]-[C:5](-[OH;D1;+0:7])-[CH2;D2;+0:6]-[NH;D2;+0:3]-[C:2]-[C:1] | 75.2 | [{"value": 75.0, "product": "OCCNCC(COCC(CCCCCCCCCCCCCCCC)O)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.2, "product": "OCCNCC(COCC(CCCCCCCCCCCCCCCC)O)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A 300-ml flask equipped with a stirrer, reflux tube and dropping funnel was charged with 40.5 g (0.66 mol) of ethanolamine and 8.6 g of ethanol. While heating and stirring the mixture at 80° C., an ethanol solution of 4.08 g (11.8 mmol) of 2-hydroxyoctadecyl glycidyl ether was added dropwise over 3 hours. After the res... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | null | null | C(C)O | 80 | null | CCCCCCCCCCCCCCCCC(O)COCC1CO1.NCCO>C(C)O>CCCCCCCCCCCCCCCCC(O)COCC(O)CNCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-31b708e4b55e4146a82a5bb5a9af3de8 | CCCCC(CC)CBr.OCCCCCCCCCCO>>CCCCC(CC)COCCCCCCCCCCO | C(C)C(CBr)CCCC.C(CCCCCCCCCO)O.[OH-].[K+]>>C(C)C(COCCCCCCCCCCO)CCCC | Br[CH2:8][CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][CH3:7].[OH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20] | CCCCC(CC)CBr.OCCCCCCCCCCO | CCCCC(CC)COCCCCCCCCCCO | null | null | C=1(C(=CC=CC1)C)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | null | Br-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2](-[C:3])-[C:4] | 72.1 | [{"value": 72.0, "product": "C(C)C(COCCCCCCCCCCO)CCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 72.1, "product": "C(C)C(COCCCCCCCCCCO)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | HOUR | A 1-liter flask equipped with a stirrer and distiller was charged with 25 g (0.14 mol) of 1,10-decanediol, 8.09 g (0.14 mol) of KOH and 300 ml of xylene, and the resultant mixture was heated at 120° C. for 1 hour, thereby distilling off water formed. To this reaction mixture, were added 23.1 g (0.12 mol) of 2-ethylhexy... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | null | HBr | C=1(C(=CC=CC1)C)C | null | 15 | CCCCC(CC)CBr.OCCCCCCCCCCO>C=1(C(=CC=CC1)C)C>CCCCC(CC)COCCCCCCCCCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-aca60743900142f7968a0bb1a46a2668 | CCCCC(CC)COCCCCCCCCCCO.ClCC1CO1>>CCCCC(CC)COCCCCCCCCCCOCC1CO1 | C(C)C(COCCCCCCCCCCO)CCCC.C(Cl)C1CO1.[OH-].[Na+]>>C(C1CO1)OCCCCCCCCCCOCC(CCCC)CC | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20].Cl[CH2:21][CH:22]1[CH2:23][O:24]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][... | CCCCC(CC)COCCCCCCCCCCO.ClCC1CO1 | CCCCC(CC)COCCCCCCCCCCOCC1CO1 | null | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC | CCCCCC | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | dd3f9c60e1f90d961a7c01d970ae213561355ee1451f276a3b04696e4b6fae5c | 46a6e883cf919b4006e69abfdfd883f458f55c08b3200960c6a5b57c4139fbca | C1CO1 | Cl-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1.[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]1-[#8:3]-[C:4]-1 | 82.6 | [{"value": 82.6, "product": "C(C1CO1)OCCCCCCCCCCOCC(CCCC)CC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.5, "product": "C(C1CO1)OCCCCCCCCCCOCC(CCCC)CC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | 2 | HOUR | A 200-ml flask equipped with a stirrer, reflux tube and dropping funnel was charged with 24.8 g (87 mmol) of 10-(2-ethylhexyloxy)decanol, 17.7 g (0.191 mol) of epichlorohydrin, 1.4 g (4.4 mmol) of tetrabutylammonium bromide and 25 ml of hexane. While stirring the mixture at 40° C., 29.2 g (0.35 mol) of a 48% aqueous so... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Primary alcohol | Ether | null | null | C1CO1 | HCl | [Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.CCCCCC | 40 | 2 | CCCCC(CC)COCCCCCCCCCCO.ClCC1CO1>[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC.CCCCCC>CCCCC(CC)COCCCCCCCCCCOCC1CO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-ad4349523f614af097d0bd73d457fcbf | CCCCC(CC)COCCCCCCCCCCOCC1CO1.NCCO>>CCCCC(CC)COCCCCCCCCCCOCC(O)CNCCO | C(O)CN.C(C1CO1)OCCCCCCCCCCOCC(CCCC)CC>>OCCNCC(COCCCCCCCCCCOCC(CCCC)CC)O | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH:22]1[O:23][CH2:24]1.[NH2:25][CH2:26][CH2:27][OH:28]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([CH2:6][CH3:7])[CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:... | CCCCC(CC)COCCCCCCCCCCOCC1CO1.NCCO | CCCCC(CC)COCCCCCCCCCCOCC(O)CNCCO | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | null | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:4]-[C:5](-[OH;D1;+0:7])-[CH2;D2;+0:6]-[NH;D2;+0:3]-[C:2]-[C:1] | 68.4 | [{"value": 68.0, "product": "OCCNCC(COCCCCCCCCCCOCC(CCCC)CC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.4, "product": "OCCNCC(COCCCCCCCCCCOCC(CCCC)CC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A 200-ml two-necked flask equipped with a stirrer, reflux tube and dropping funnel was charged with 32.7 g (0.54 mol) of ethanolamine and 10.1 g of ethanol. While heating and stirring the mixture at 80° C., 1.76 g (5.14 mmol) of 10-(2-ethylhexyloxy)decyl glycidyl ether were added dropwise over 2 hours. After the result... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | null | null | C(C)O | 80 | null | CCCCC(CC)COCCCCCCCCCCOCC1CO1.NCCO>C(C)O>CCCCC(CC)COCCCCCCCCCCOCC(O)CNCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-47ed777a87bd4c2eaf51117084ffdcc4 | CCCCOC(=O)CCCCCCCCCCCOCC1CO1.NCCO>>CCCCOC(=O)CCCCCCCCCCCOCC(O)CNCCO | C(O)CN.C(C)O.C(C)O.O1C(COCCCCCCCCCCCC(=O)OCCCC)C1>>OC(COCCCCCCCCCCCC(=O)OCCCC)CNCCO | [CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]1[O:22][CH2:23]1.[NH2:24][CH2:25][CH2:26][OH:27]>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:7])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][... | CCCCOC(=O)CCCCCCCCCCCOCC1CO1.NCCO | CCCCOC(=O)CCCCCCCCCCCOCC(O)CNCCO | null | null | O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | null | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:4]-[C:5](-[OH;D1;+0:7])-[CH2;D2;+0:6]-[NH;D2;+0:3]-[C:2]-[C:1] | 55.4 | [{"value": 55.4, "product": "OC(COCCCCCCCCCCCC(=O)OCCCC)CNCCO", "details": "PERCENTYIELD", "is_desired": false}, {"value": 55.4, "product": "OC(COCCCCCCCCCCCC(=O)OCCCC)CNCCO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A 100-ml flask equipped with a stirrer and dropping funnel was charged with 23.7 g (250 mmol) of ethanolamine and 23.7 g of ethanol. While stirring the mixture at 80° C., an ethanol solution of 8.20 g (25 mmol) of butyl 12-(2,3-epoxypropoxy)-dodecanate was added dropwise over 1 hour. After completion of the reaction, w... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | null | null | O | 80 | null | CCCCOC(=O)CCCCCCCCCCCOCC1CO1.NCCO>O>CCCCOC(=O)CCCCCCCCCCCOCC(O)CNCCO |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-3d817c6e53494262853c2c135e11aa2f | C=CCCCCCCCCCOCC1CO1.CCCC[SiH](C)C>>CCCC[Si](C)(C)CCCCCCCCCCCOCC1CO1 | C(C1CO1)OCCCCCCCCCC=C.C(CCC)[SiH](C)C>>C(C1CO1)OCCCCCCCCCCC[Si](C)(C)CCCC | [CH2:8]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]1[CH2:22][O:23]1.[CH3:1][CH2:2][CH2:3][CH2:4][SiH:5]([CH3:6])[CH3:7]>>[CH3:1][CH2:2][CH2:3][CH2:4][Si:5]([CH3:6])([CH3:7])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19... | C=CCCCCCCCCCOCC1CO1.CCCC[SiH](C)C | CCCC[Si](C)(C)CCCCCCCCCCCOCC1CO1 | null | null | null | Miscellaneous | OtherReaction | d58f0e45f5e65f348e65093ae169a3aefe37d609d0cf033474e49e11b89de8cb | 74f01156541c6fb58c50400af9f4c8ee92e9ad7fe3a34f04ffeae72094d3e765 | C1CO1 | [C:1]-[C:2]-[CH;D2;+0:3]=[CH2;D1;+0:4].[C:5]-[C:6]-[SiH;D3;+0:7](-[C;D1;H3:8])-[C;D1;H3:9]>>[C:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[Si;H0;D4;+0:7](-[C;D1;H3:8])(-[C;D1;H3:9])-[C:6]-[C:5] | 82.6 | [{"value": 82.6, "product": "C(C1CO1)OCCCCCCCCCCC[Si](C)(C)CCCC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.6, "product": "C(C1CO1)OCCCCCCCCCCC[Si](C)(C)CCCC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 24 | HOUR | A 100-ml flask equipped with a stirrer was charged with 13.6 g (60 mmol) of 10-undecenyl glycidyl ether, 5.8 g (50 mmol) of butyldimethylsilane and 4 mg (0.01 mmol) of H2PtCl6. The contents were stirred at 60° C. for 24 hours. The resultant reaction mixture was distilled under reduced pressure (145°-154° C./6×10-3 Torr... | 10.6084/m9.figshare.5104873.v1 | null | Allyl | Silyl protective group | null | null | C1CO1 | null | null | 60 | 24 | C=CCCCCCCCCCOCC1CO1.CCCC[SiH](C)C>>CCCC[Si](C)(C)CCCCCCCCCCCOCC1CO1 |
ord_dataset-018fd0e1351f4fd09b20fcddd97b4c7a | ord-2859afa0baa6419ab73c46a66ac9120c | CCCC[Si](C)(C)CCCCCCCCCCCOCC1CO1.NCCO>>CCCC[Si](C)(C)CCCCCCCCCCCOCC(O)CNCCO | C(C1CO1)OCCCCCCCCCCC[Si](C)(C)CCCC.C(O)CN.N#N.C(O)CN>>OCCNCC(COCCCCCCCCCCC[Si](C)(C)CCCC)O | [CH3:1][CH2:2][CH2:3][CH2:4][Si:5]([CH3:6])([CH3:7])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]1[O:22][CH2:23]1.[NH2:24][CH2:25][CH2:26][OH:27]>>[CH3:1][CH2:2][CH2:3][CH2:4][Si:5]([CH3:6])([CH3:7])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:... | CCCC[Si](C)(C)CCCCCCCCCCCOCC1CO1.NCCO | CCCC[Si](C)(C)CCCCCCCCCCCOCC(O)CNCCO | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | f75f8fec78b0ee9c8e880101c8c57c2a3edaac070bc7ad0163a34826e2af8c65 | 04c78336d85647f6dca3040f384f77009d1b541aac7f8ccf33aa9798091ceab8 | null | [C:1]-[C:2]-[NH2;D1;+0:3].[C:4]-[C:5]1-[CH2;D2;+0:6]-[O;H0;D2;+0:7]-1>>[C:4]-[C:5](-[OH;D1;+0:7])-[CH2;D2;+0:6]-[NH;D2;+0:3]-[C:2]-[C:1] | 73.3 | [{"value": 73.0, "product": "OCCNCC(COCCCCCCCCCCC[Si](C)(C)CCCC)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.3, "product": "OCCNCC(COCCCCCCCCCCC[Si](C)(C)CCCC)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A 100-ml two-necked flask equipped with a stirrer, dropping funnel and N2 inlet tube was charged with 4.58 g (75 mmol) of ethanolamine and 9.2 g of ethanol. The contents were heated to 80° C. with stirring in an N2 atmosphere, and an ethanol solution of 1.71 g (5 mmol) of 11-(butyldimethylsilyl)undecyl glycidyl ether w... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine | Secondary alcohol.Secondary amine | C1CO1 | null | null | null | C(C)O | 80 | null | CCCC[Si](C)(C)CCCCCCCCCCCOCC1CO1.NCCO>C(C)O>CCCC[Si](C)(C)CCCCCCCCCCCOCC(O)CNCCO |
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