dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1ab555f16b654ade937dccaeb6cb5b60 | Cc1cc(C)c(-c2c3nc(c(-c4ccc(C(C)(C)C)cc4)c4ccc([nH]4)c(C4OCC(C)(C)CO4)c4nc(c(-c5ccc(C(C)(C)C)cc5)c5ccc2[nH]5)C=C4)C=C3)c(C)c1>>Cc1cc(C)c(-c2c3nc(c(-c4ccc(C(C)(C)C)cc4)c4ccc([nH]4)c(C=O)c4nc(c(-c5ccc(C(C)(C)C)cc5)c5ccc2[nH]5)C=C4)C=C3)c(C)c1 | C(C)(C)(C)C1=CC=C(C=C1)C=1C2=CC=C(N2)C(=C2C=CC(C(=C3C=CC(=C(C=4C=CC1N4)C4OCC(CO4)(C)C)N3)C3=CC=C(C=C3)C(C)(C)C)=N2)C2=C(C=C(C=C2C)C)C.C(=O)(C(F)(F)F)O.O>>C(C)(C)(C)C1=CC=C(C=C1)C=1C2=CC=C(N2)C(=C2C=CC(C(=C3C=CC(=C(C=4C=CC1N4)C=O)N3)C3=CC=C(C=C3)C(C)(C)C)=N2)C2=C(C=C(C=C2C)C)C | CC1(C)CO[CH:28]([c:27]2[c:25]3[cH:24][cH:23][c:22]([c:11](-[c:12]4[cH:13][cH:14][c:15]([C:16]([CH3:17])([CH3:18])[CH3:19])[cH:20][cH:21]4)[c:10]4[n:9][c:8]([c:7](-[c:6]5[c:4]([CH3:5])[cH:3][c:2]([CH3:1])[cH:55][c:53]5[CH3:54])[c:47]5[cH:46][cH:45][c:44]([c:33](-[c:34]6[cH:35][cH:36][c:37]([C:38]([CH3:39])([CH3:40])[CH3... | Cc1cc(C)c(-c2c3nc(c(-c4ccc(C(C)(C)C)cc4)c4ccc([nH]4)c(C4OCC(C)(C)CO4)c4nc(c(-c5ccc(C(C)(C)C)cc5)c5ccc2[nH]5)C=C4)C=C3)c(C)c1 | Cc1cc(C)c(-c2c3nc(c(-c4ccc(C(C)(C)C)cc4)c4ccc([nH]4)c(C=O)c4nc(c(-c5ccc(C(C)(C)C)cc5)c5ccc2[nH]5)C=C4)C=C3)c(C)c1 | null | null | C(Cl)Cl | Miscellaneous | Acetal hydrolysis to aldehyde | c0e8259a4c04433c939fe17907d7eafe1c52bcb535318030bf0e1cb6f82c0712 | 84d5a69453aa750f462aa94a6bf2116fc17c5d88a9619aaa9eefb74b0c09848d | C1=Cc2nc1cc1ccc([nH]1)c(-c1ccccc1)c1nc(c(-c3ccccc3)c3ccc([nH]3)c2-c2ccccc2)C=C1 | C-C1(-C)-C-O-[CH;D3;+0:1](-[c:2](:[c:3](:[c:4]):[#7;a:5]:[c:6]):[c:7]2:[#7;a:8]:[c:9]-[C:10]=[C:11]-2)-[O;H0;D2;+0:12]-C-1>>[O;H0;D1;+0:12]=[CH;D2;+0:1]-[c:2](:[c:3](:[c:4]):[#7;a:5]:[c:6]):[c:7]1:[#7;a:8]:[c:9]-[C:10]=[C:11]-1 | 96.5 | [{"value": 92.0, "product": "C(C)(C)(C)C1=CC=C(C=C1)C=1C2=CC=C(N2)C(=C2C=CC(C(=C3C=CC(=C(C=4C=CC1N4)C=O)N3)C3=CC=C(C=C3)C(C)(C)C)=N2)C2=C(C=C(C=C2C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.5, "product": "C(C)(C)(C)C1=CC=C(C=C1)C=1C2=CC=C(N2)C(=C2C=CC(C(=C3C=CC(=C(C=4C=CC1N4)C=O)N3)C3=CC=C(C=C... | null | null | 2.5 | HOUR | Following a general procedure,22 a solution of 4 (43 mg, 0.05 mmol) in CH2Cl2 (5 mL) was treated with TFA/water (0.5 mL, 1:1) to give a biphasic solution. After stirring at room temperature for 2.5 h, CH2Cl2 was added. The organic layer was washed (saturated aqueous NaHCO3 and brine), dried (Na2SO4), concentrated, and ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aldehyde | C1COCOC1 | null | c1ccccc1.c1ccccc1.c1ccccc1.C1=Cc2cc3ccc(cc4nc(cc5ccc(cc1n2)n5)C=C4)n3 | HO- | C(Cl)Cl | null | 2.5 | Cc1cc(C)c(-c2c3nc(c(-c4ccc(C(C)(C)C)cc4)c4ccc([nH]4)c(C4OCC(C)(C)CO4)c4nc(c(-c5ccc(C(C)(C)C)cc5)c5ccc2[nH]5)C=C4)C=C3)c(C)c1>C(Cl)Cl>Cc1cc(C)c(-c2c3nc(c(-c4ccc(C(C)(C)C)cc4)c4ccc([nH]4)c(C=O)c4nc(c(-c5ccc(C(C)(C)C)cc5)c5ccc2[nH]5)C=C4)C=C3)c(C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac1066e2a00a46a68a42da26e6ac36ce | CC(C)(CO)CO.O=CC(=O)O>>CC1(C)COC(C(=O)O)OC1 | O.C(C=O)(=O)O.CC(CO)(CO)C>>C(=O)(O)C1OCC(CO1)(C)C | [CH3:1][C:2]([CH3:3])([CH2:4][OH:5])[CH2:11][OH:10].O=[CH:6][C:7](=[O:8])[OH:9]>>[CH3:1][C:2]1([CH3:3])[CH2:4][O:5][CH:6]([C:7](=[O:8])[OH:9])[O:10][CH2:11]1 | CC(C)(CO)CO.O=CC(=O)O | CC1(C)COC(C(=O)O)OC1 | null | null | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 09991f411aacffcc904d1b314d4846ed4bc3fcd70ecd0a878cedf349d9162730 | 7ac65b5a5f576337ce8e86e0130eb9b4757ca21b2419a0e82bbdfd5def30ee73 | C1COCOC1 | O=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].[OH;D1;+0:5]-[C:6]-[C:7]-[C:8]-[OH;D1;+0:9]>>[O;D1;H0:3]=[C:2](-[O;D1;H1:4])-[CH;D3;+0:1]1-[O;H0;D2;+0:5]-[C:6]-[C:7]-[C:8]-[O;H0;D2;+0:9]-1 | 73.4 | [{"value": 73.0, "product": "C(=O)(O)C1OCC(CO1)(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 73.4, "product": "C(=O)(O)C1OCC(CO1)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following a general procedure,23 a mixture of glyoxylic acid monohydrate (5.0 g, 54 mmol), 2,2-dimethyl 1,3-propanediol (8.5 g, 81 mmol) and Amberlyst-15 ion-exchange resin (100 mg) in benzene (140 mL) was refluxed for 15 h in a flask fitted with a Dean-Stark apparatus. The reaction mixture was filtered. The filtrate w... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary alcohol.Primary alcohol | Ether.Ether | null | C1COCOC1 | C1COCOC1 | HO- | C1=CC=CC=C1 | null | null | CC(C)(CO)CO.O=CC(=O)O>C1=CC=CC=C1>CC1(C)COC(C(=O)O)OC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-de88f6777451494bbb26cbe1ef4f25d6 | CC1(C)COC(c2c3nc(c(-c4ccccc4)c4ccc([nH]4)c(C4OCC(C)(C)CO4)c4nc(c(-c5ccccc5)c5ccc2[nH]5)C=C4)C=C3)OC1>>O=Cc1c2nc(c(-c3ccccc3)c3ccc([nH]3)c(C=O)c3nc(c(-c4ccccc4)c4ccc1[nH]4)C=C3)C=C2 | C(Cl)Cl.C(C)(=O)OCC.CC1(COC(OC1)C=1C2=CC=C(N2)C(=C2C=CC(C(=C3C=CC(=C(C=4C=CC1N4)C4=CC=CC=C4)N3)C3OCC(CO3)(C)C)=N2)C2=CC=CC=C2)C.C(=O)(C(F)(F)F)O.O>>C(=O)C=1C2=CC=C(N2)C(=C2C=CC(C(=C3C=CC(=C(C=4C=CC1N4)C4=CC=CC=C4)N3)C=O)=N2)C2=CC=CC=C2 | CC1(C)CO[CH:2]([c:3]2[c:4]3[n:5][c:6]([c:7](-[c:8]4[cH:9][cH:10][cH:11][cH:12][cH:13]4)[c:14]4[cH:15][cH:16][c:17]([nH:18]4)[c:19]([CH:20]4OCC(C)(C)C[O:21]4)[c:22]4[n:23][c:24]([c:25](-[c:26]5[cH:27][cH:28][cH:29][cH:30][cH:31]5)[c:32]5[cH:33][cH:34][c:35]2[nH:36]5)[CH:37]=[CH:38]4)[CH:39]=[CH:40]3)[O:1]C1>>[O:1]=[CH:2... | CC1(C)COC(c2c3nc(c(-c4ccccc4)c4ccc([nH]4)c(C4OCC(C)(C)CO4)c4nc(c(-c5ccccc5)c5ccc2[nH]5)C=C4)C=C3)OC1 | O=Cc1c2nc(c(-c3ccccc3)c3ccc([nH]3)c(C=O)c3nc(c(-c4ccccc4)c4ccc1[nH]4)C=C3)C=C2 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 25afb5e990cc694e9d051666ccb4295610f2a73c81de017ecb8368b0c5bb9111 | e21cb1bdfd69a4be8a457a57bfa9f8563cedb23c177c9d451a21afc104d55beb | C1=Cc2nc1cc1ccc([nH]1)c(-c1ccccc1)c1nc(cc3ccc([nH]3)c2-c2ccccc2)C=C1 | C-C1(-C)-C-O-[CH;D3;+0:1](-[c:2](:[c:3](:[c:4]):[#7;a:5]:[c:6]):[c:7]2:[#7;a:8]:[c:9]-[C:10]=[C:11]-2)-[O;H0;D2;+0:12]-C-1.C-C1(-C)-C-O-[CH;D3;+0:13](-[c:14](:[c:15](:[c:16]):[#7;a:17]:[c:18]):[c:19]2:[#7;a:20]:[c:21]-[C:22]=[C:23]-2)-[O;H0;D2;+0:24]-C-1>>[O;H0;D1;+0:12]=[CH;D2;+0:1]-[c:2](:[c:3](:[c:4]):[#7;a:5]:[c:6]... | 83 | [{"value": 83.0, "product": "C(=O)C=1C2=CC=C(N2)C(=C2C=CC(C(=C3C=CC(=C(C=4C=CC1N4)C4=CC=CC=C4)N3)C=O)=N2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.0, "product": "C(=O)C=1C2=CC=C(N2)C(=C2C=CC(C(=C3C=CC(=C(C=4C=CC1N4)C4=CC=CC=C4)N3)C=O)=N2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD... | null | null | 3 | DAY | As described for 5, a solution of 14 (30 mg, 44 μmol) in CH2Cl2 (5.0 mL) was treated with TFA/water (2.0 mL, 1:1) with stirring at room temperature for 3 days. Standard workup including chromatography (silica, CH2Cl2/ethyl acetate) gave a purple green solid (18.7 mg, 83%): IR (neat) 1673, 1550, 1120 cm−1; 1H NMR δ −2.3... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Aldehyde.Aldehyde | C1COCOC1.C1COCOC1 | null | c1ccccc1.c1ccccc1.C1=Cc2cc3ccc(cc4nc(cc5ccc(cc1n2)n5)C=C4)n3 | HO- | C(Cl)Cl | null | 72 | CC1(C)COC(c2c3nc(c(-c4ccccc4)c4ccc([nH]4)c(C4OCC(C)(C)CO4)c4nc(c(-c5ccccc5)c5ccc2[nH]5)C=C4)C=C3)OC1>C(Cl)Cl>O=Cc1c2nc(c(-c3ccccc3)c3ccc([nH]3)c(C=O)c3nc(c(-c4ccccc4)c4ccc1[nH]4)C=C3)C=C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-0986f615c1f044319bcf86fa07aa69f1 | CC1(C)COC(c2c3nc(c(C4OCC(C)(C)CO4)c4ccc([nH]4)c(-c4ccccc4)c4nc(c(-c5ccccc5)c5ccc2[nH]5)C=C4)C=C3)OC1>>O=Cc1c2nc(c(C=O)c3ccc([nH]3)c(-c3ccccc3)c3nc(c(-c4ccccc4)c4ccc1[nH]4)C=C3)C=C2 | CC1(COC(OC1)C=1C2=CC=C(N2)C(=C2C=CC(C(=C3C=CC(=C(C=4C=CC1N4)C4OCC(CO4)(C)C)N3)C3=CC=CC=C3)=N2)C2=CC=CC=C2)C.C(=O)(C(F)(F)F)O.O>>C(=O)C=1C2=CC=C(N2)C(=C2C=CC(C(=C3C=CC(=C(C=4C=CC1N4)C=O)N3)C3=CC=CC=C3)=N2)C2=CC=CC=C2 | CC1(C)CO[CH:2]([c:3]2[c:4]3[n:5][c:6]([c:7]([CH:8]4OCC(C)(C)C[O:9]4)[c:10]4[cH:11][cH:12][c:13]([nH:14]4)[c:15](-[c:16]4[cH:17][cH:18][cH:19][cH:20][cH:21]4)[c:22]4[n:23][c:24]([c:25](-[c:26]5[cH:27][cH:28][cH:29][cH:30][cH:31]5)[c:32]5[cH:33][cH:34][c:35]2[nH:36]5)[CH:37]=[CH:38]4)[CH:39]=[CH:40]3)[O:1]C1>>[O:1]=[CH:2... | CC1(C)COC(c2c3nc(c(C4OCC(C)(C)CO4)c4ccc([nH]4)c(-c4ccccc4)c4nc(c(-c5ccccc5)c5ccc2[nH]5)C=C4)C=C3)OC1 | O=Cc1c2nc(c(C=O)c3ccc([nH]3)c(-c3ccccc3)c3nc(c(-c4ccccc4)c4ccc1[nH]4)C=C3)C=C2 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 25afb5e990cc694e9d051666ccb4295610f2a73c81de017ecb8368b0c5bb9111 | e21cb1bdfd69a4be8a457a57bfa9f8563cedb23c177c9d451a21afc104d55beb | C1=Cc2cc3ccc([nH]3)c(-c3ccccc3)c3nc(c(-c4ccccc4)c4ccc(cc1n2)[nH]4)C=C3 | C-C1(-C)-C-O-[CH;D3;+0:1](-[c:2](:[c:3](:[c:4]):[#7;a:5]:[c:6]):[c:7]2:[#7;a:8]:[c:9](:[c:10](-[CH;D3;+0:11]3-O-C-C(-C)(-C)-C-[O;H0;D2;+0:12]-3):[c:13](:[c:14]):[#7;a:15]:[c:16])-[C:17]=[C:18]-2)-[O;H0;D2;+0:19]-C-1>>[O;H0;D1;+0:19]=[CH;D2;+0:1]-[c:2](:[c:3](:[c:4]):[#7;a:5]:[c:6]):[c:7]1:[#7;a:8]:[c:9](:[c:10](-[CH;D2... | 88 | [{"value": 88.0, "product": "C(=O)C=1C2=CC=C(N2)C(=C2C=CC(C(=C3C=CC(=C(C=4C=CC1N4)C=O)N3)C3=CC=CC=C3)=N2)C2=CC=CC=C2", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.8, "product": "C(=O)C=1C2=CC=C(N2)C(=C2C=CC(C(=C3C=CC(=C(C=4C=CC1N4)C=O)N3)C3=CC=CC=C3)=N2)C2=CC=CC=C2", "details": "CALCULATEDPERCENTYIELD... | null | null | null | null | As described for 5, a solution of 17 (30 mg, 44 μmol) in CH2Cl2 (5.0 mL) was treated with TFA/water (2.0 mL, 1:1) at room temperature for 3 days. The standard workup including chromatography (silica, CHCl3/hexanes) afforded a purple solid (19.8 mg, 88%): IR (neat) 1672, 1548, 1166 cm−1; 1H NMR δ −2.19 (s, 2H), 7.76-7.8... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Ether.Ether | Aldehyde.Aldehyde | C1COCOC1.C1COCOC1 | null | c1ccccc1.c1ccccc1.C1=Cc2cc3ccc(cc4nc(cc5ccc(cc1n2)n5)C=C4)n3 | HO- | C(Cl)Cl | null | null | CC1(C)COC(c2c3nc(c(C4OCC(C)(C)CO4)c4ccc([nH]4)c(-c4ccccc4)c4nc(c(-c5ccccc5)c5ccc2[nH]5)C=C4)C=C3)OC1>C(Cl)Cl>O=Cc1c2nc(c(C=O)c3ccc([nH]3)c(-c3ccccc3)c3nc(c(-c4ccccc4)c4ccc1[nH]4)C=C3)C=C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3f464347dcc84cd7a0f1603cd8663c97 | CCCCC=O.O=C1C=CCC1>>CCCCC(O)C1=CCCC1=O | C1(C=CCC1)=O.C(CCCC)=O.C(CCC)P(CCCC)CCCC>>OC(CCCC)C=1C(CCC1)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH:5]=[O:6].[CH:7]1=[CH:8][CH2:9][CH2:10][C:11]1=[O:12]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([OH:6])[C:7]1=[CH:8][CH2:9][CH2:10][C:11]1=[O:12] | CCCCC=O.O=C1C=CCC1 | CCCCC(O)C1=CCCC1=O | null | null | C1CCOC1 | C-C Coupling | OtherReaction | d982483ca196073df722bce8466788858afd4e2743b087e877ba8e9bd813efc2 | 7d7139092067ff475e8e8a4ad6adb4833600ca969e282ed08dc56c016dccb864 | O=C1C=CCC1 | [C:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4].[O;D1;H0:5]=[C:6]1-[C:7]-[C:8]-[C:9]=[CH;D2;+0:10]-1>>[C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[C;H0;D3;+0:10]1=[C:9]-[C:8]-[C:7]-[C:6]-1=[O;D1;H0:5] | 92 | [{"value": 92.0, "product": "OC(CCCC)C=1C(CCC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of cyclopentenone (1.23 g, 15 mmol), pentanal (1.94 g, 22.5 mmol), rac-1,1′-bi-2-naphthol (429 mg, 1.5 mmol) and tributyl phosphine (606 mg, 3 mmol) in dry THF (12 ml) was stirred at 20° C. under Argon for 3 hours. The solution was then passed through a short column of SiO2 (cyclohexane/Et2O 6:4) to obtain t... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone.Secondary alcohol | C1=CCCC1 | C1=CCCC1 | C1=CCCC1 | null | C1CCOC1 | null | null | CCCCC=O.O=C1C=CCC1>C1CCOC1>CCCCC(O)C1=CCCC1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-157c9ed3dcb14c5a90079d5afbbf6d01 | CC(C)(C)C(=O)O.CC(C)(C)C([O-])([O-])[O-].CCCCC(O)C1=CCCC1=O>>CCCCC=C1C(=O)CCC1CC(=O)OC | OC(CCCC)C=1C(CCC1)=O.C(C(C)(C)C)(=O)O.CC(C([O-])([O-])[O-])(C)C>>O=C1C(C(CC1)CC(=O)OC)=CCCCC | C[C:12](C)(C)[C:13](=[O:14])[OH:15].CC(C)(C([O-])([O-])[O-])[CH3:16].O[CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[C:6]1=[CH:11][CH2:10][CH2:9][C:7]1=[O:8]>>[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]=[C:6]1[C:7](=[O:8])[CH2:9][CH2:10][CH:11]1[CH2:12][C:13](=[O:14])[O:15][CH3:16] | CC(C)(C)C(=O)O.CC(C)(C)C([O-])([O-])[O-].CCCCC(O)C1=CCCC1=O | CCCCC=C1C(=O)CCC1CC(=O)OC | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 5a427e86cb728b62e97e3a9b8761cbd0f04cf303e69df89d58c25172edfe9b0c | bc537d2de7ba3dc6bb8984e8defe531f2d8495eed6447f40b3da4cb7e1cd3a44 | [CH]=C1CCCC1=O | C-C(-C)(-[CH3;D1;+0:1])-C(-[O-])(-[O-])-[O-].C-[C;H0;D4;+0:2](-C)(-C)-[C:3](=[O;D1;H0:4])-[OH;D1;+0:5].O-[CH;D3;+0:6](-[C:7]-[C:8])-[C;H0;D3;+0:9]1=[CH;D2;+0:10]-[C:11]-[C:12]-[C:13]-1=[O;D1;H0:14]>>[C:8]-[C:7]-[CH;D2;+0:6]=[C;H0;D3;+0:9]1-[C:13](=[O;D1;H0:14])-[C:12]-[C:11]-[CH;D3;+0:10]-1-[CH2;D2;+0:2]-[C:3](=[O;D1;H... | 88 | [{"value": 88.0, "product": "O=C1C(C(CC1)CC(=O)OC)=CCCCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 2-(1-hydroxypentyl)-2-cyclopenten-1-one (720 mg, 4.2 mmol) and pivalic acid (100 mg, 0.98 mmol) in trimethylorthoacetate (5 ml, 39.3 mmol) was heated at 115° C. for 3 hours with distillation of MeOH. The concentrated reaction mixture was bulb-to-bulb distilled to afford the title compound in 88% yield and ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Secondary alcohol | Ketone.Ester | C1=CCCC1 | C1CCCC1 | C1CCCC1 | HO- | CO | null | null | CC(C)(C)C(=O)O.CC(C)(C)C([O-])([O-])[O-].CCCCC(O)C1=CCCC1=O>CO>CCCCC=C1C(=O)CCC1CC(=O)OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-2bb76cb3b2ce428c869ec19cde483fb2 | O=C(F)C(F)(C(F)(F)F)C(F)(F)F.OCCCOCCCO>>O=C(OCCCOCCCOC(=O)C(F)(C(F)(F)F)C(F)(F)F)C(F)(C(F)(F)F)C(F)(F)F | OCCCOCCCO.FC(=O)C(F)(C(F)(F)F)C(F)(F)F>>C(F)(C(F)(F)F)(C(F)(F)F)C(=O)OCCCOCCCOC(=O)C(F)(C(F)(F)F)C(F)(F)F | [C:12](=[O:13])([C:14]([F:15])([C:16]([F:17])([F:19])[F:23])[C:30]([F:31])([F:32])[F:33])[F:25].[OH:1][CH2:2][CH2:9][CH2:8][O:7][CH2:6][CH2:5][CH2:4][OH:3]>>[O:1]=[C:2]([O:3][CH2:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][CH2:10][O:11][C:12](=[O:13])[C:14]([F:15])([C:16]([F:17])([F:18])[F:19])[C:20]([F:21])([F:22])[F:23])[C:2... | O=C(F)C(F)(C(F)(F)F)C(F)(F)F.OCCCOCCCO | O=C(OCCCOCCCOC(=O)C(F)(C(F)(F)F)C(F)(F)F)C(F)(C(F)(F)F)C(F)(F)F | null | null | null | Acylation | OtherReaction | e4d30fe38ff87c2481c7f22c259cbc2c34987aa16c61c63d81a7a542c909ff2e | 599255592d198b68bb8a6598b0274efd9cfd7815bf5288af70012aec84cc494d | null | [#8:1]-[C:2]-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[OH;D1;+0:5].[C:6]-[C:7]-[OH;D1;+0:8].[F;D1;H0:9]-[C;H0;D4;+0:10](-[C;H0;D3;+0:11](-[F;H0;D1;+0:12])=[O;D1;H0:13])(-[C;H0;D4;+0:14](-[F;D1;H0:15])(-[F;D1;H0:16])-[F;H0;D1;+0:17])-[C;H0;D4;+0:18](-[F;D1;H0:19])(-[F;D1;H0:20])-[F;D1;H0:21]>>[#8:1]-[C:2]-[CH2;D2;+0:3]-[C:22]-[#8:23... | 92.1 | [{"value": 81.0, "product": "C(F)(C(F)(F)F)(C(F)(F)F)C(=O)OCCCOCCCOC(=O)C(F)(C(F)(F)F)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.1, "product": "C(F)(C(F)(F)F)(C(F)(F)F)C(=O)OCCCOCCCOC(=O)C(F)(C(F)(F)F)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 7 | HOUR | HO(CH2)3O(CH2)3OH (10 g) was loaded into an autoclave and stirred in a sealed state, and FCOCF(CF3)2 (36.95 g) was fed over 7 hours at room temperature with occasional pauses for bubbling with nitrogen gas under unsealed conditions. After the feeding, the reaction solution was stirred at room temperature for 1 hour and... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trifluoro group.Trifluoro group.Tertiary halide.Primary alcohol.Primary alcohol | Trifluoro group.Trifluoro group.Trifluoro group.Trifluoro group.Tertiary halide.Tertiary halide.Ester.Ester | null | null | null | Other | null | null | 7 | O=C(F)C(F)(C(F)(F)F)C(F)(F)F.OCCCOCCCO>>O=C(OCCCOCCCOC(=O)C(F)(C(F)(F)F)C(F)(F)F)C(F)(C(F)(F)F)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bb577df9e2c347328109835fd6a602b1 | Cc1ccc(S(=O)(=O)OC(C)COC(C)(C)C)cc1.OCCCO>>CC(COC(C)(C)C)OCCCO | Cl.[OH-].[K+].OCCCO.S(=O)(=O)(C1=CC=C(C)C=C1)OC(C)COC(C)(C)C>>OCCCOC(C)COC(C)(C)C | Cc1ccc(S(=O)(=O)O[CH:2]([CH3:1])[CH2:3][O:4][C:5]([CH3:6])([CH3:7])[CH3:8])cc1.[OH:9][CH2:10][CH2:11][CH2:12][OH:13]>>[CH3:1][CH:2]([CH2:3][O:4][C:5]([CH3:6])([CH3:7])[CH3:8])[O:9][CH2:10][CH2:11][CH2:12][OH:13] | Cc1ccc(S(=O)(=O)OC(C)COC(C)(C)C)cc1.OCCCO | CC(COC(C)(C)C)OCCCO | null | null | O1CCOCC1 | Heteroatom Alkylation and Arylation | OtherReaction | 14f213034e6a37dd0cb837e56b2a221a4a43776111e112dda97ccbb323c0e76d | 603fcf095026d2fb605fcefe86430c369a5441c61b94694e2075fffc1fd129c3 | null | C-c1:c:c:c(-S(=O)(=O)-O-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3]-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8]):c:c:1.[C:9]-[C:10]-[OH;D1;+0:11]>>[C:9]-[C:10]-[O;H0;D2;+0:11]-[CH;D3;+0:1](-[C;D1;H3:2])-[C:3]-[#8:4]-[C:5](-[C;D1;H3:6])(-[C;D1;H3:7])-[C;D1;H3:8] | 43.8 | [{"value": 43.8, "product": "OCCCOC(C)COC(C)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Potassium hydroxide (274.27 g) and HO(CH2)3OH (371.93 g) were added to dioxane (3 L), and then TsOCH(CH3)CH2OC(CH3)3 (700 g) prepared in Example 2-1 was added gradually. The reaction solution was refluxed with heating for 16 hours, allowed to cool, and poured onto ice (500 g), neutralized with 2 N hydrochloric acid, co... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Primary alcohol | Ether | c1ccccc1 | null | null | TsOH.HO- | O1CCOCC1 | null | null | Cc1ccc(S(=O)(=O)OC(C)COC(C)(C)C)cc1.OCCCO>O1CCOCC1>CC(COC(C)(C)C)OCCCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-86d261b188c3472ea1e89fc68be3f816 | CC(COC(C)(C)C)OCCCO>>CC(CO)OCCCO | OCCCOC(C)COC(C)(C)C.Cl>>OCCCOC(C)CO | CC(C)(C)[O:4][CH2:3][CH:2]([CH3:1])[O:5][CH2:6][CH2:7][CH2:8][OH:9]>>[CH3:1][CH:2]([CH2:3][OH:4])[O:5][CH2:6][CH2:7][CH2:8][OH:9] | CC(COC(C)(C)C)OCCCO | CC(CO)OCCCO | null | null | null | Deprotection | Ether cleavage to primary alcohol | 9614211a2a35d6177bcded67d8911ba46072c6f11693f23436d14d3c121d33af | 29a81fd08d26edc3da6d72c4958026f5af2119326dc1b4714ee5be1c41835609 | null | C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2]-[C:3]>>[C:3]-[C:2]-[OH;D1;+0:1] | 91.3 | [{"value": 91.3, "product": "OCCCOC(C)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | HO(CH2)3OCH(CH3)CH2OC(CH3)3 (203.39 g) prepared in Example 2-2 was loaded into a round-bottomed flask and stirred with 5 N hydrochloric acid (1 L) at room temperature for 43 hours. The reaction solution was concentrated with an evaporator, and then, after addition of toluene, concentrated again with an evaporator to gi... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Primary alcohol | null | null | null | Other | null | null | null | CC(COC(C)(C)C)OCCCO>>CC(CO)OCCCO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4229ab0dce14b9886f55da78a21d461 | CC(CO)OCCCO.O=C(F)C(F)(OC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(F)(F)F>>CC(COC(=O)C(F)(OC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(F)(F)F)OCCCOC(=O)C(F)(OC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(F)(F)F | C(F)(F)(F)C(F)(F)C(F)(F)OC(F)(C(F)(F)F)C(F)(F)OC(F)(C(F)(F)F)C(=O)F.OCCCOC(C)CO>>C(F)(F)(F)C(F)(F)C(F)(F)OC(F)(C(F)(F)F)C(F)(F)OC(F)(C(F)(F)F)C(=O)OCC(C)OCCCOC(=O)C(F)(C(F)(F)F)OC(F)(F)C(F)(C(F)(F)F)OC(F)(F)C(F)(F)C(F)(F)F | [CH3:1][CH:2]([CH2:3][OH:4])[O:34][CH2:35][CH2:36][CH2:37][OH:38].[C:5](=[O:6])([C:7]([F:8])([O:9][C:10]([F:11])([F:12])[C:13]([F:14])([O:15][C:16]([F:17])([F:18])[C:19]([F:20])([C:22]([F:23])([F:25])[F:59])[F:51])[C:26]([F:27])([F:28])[F:29])[C:30]([F:21])([F:48])[F:67])[F:42]>>[CH3:1][CH:2]([CH2:3][O:4][C:5](=[O:6])[... | CC(CO)OCCCO.O=C(F)C(F)(OC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(F)(F)F | CC(COC(=O)C(F)(OC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(F)(F)F)OCCCOC(=O)C(F)(OC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(F)(F)F | null | null | C(=O)(O)[O-].[Na+] | Acylation | OtherReaction | ecf64c3d7829aa41163740b7b8b48d17ced9b305fb54f4144a94331afc334222 | b5800ccc1456e0f7e50a5b399bc5dd10000c4999d7d141f4411fd3d30d4028f2 | null | [#8:1]-[C:2](-[F;D1;H0:3])(-[C;H0;D3;+0:4](-[F;H0;D1;+0:5])=[O;D1;H0:6])-[C;H0;D4;+0:7](-[F;H0;D1;+0:8])(-[F;H0;D1;+0:9])-[F;H0;D1;+0:10].[#8:11]-[C:12](-[F;D1;H0:13])(-[F;D1;H0:14])-[C;H0;D4;+0:15](-[F;D1;H0:16])(-[F;H0;D1;+0:17])-[C;H0;D4;+0:18](-[F;D1;H0:19])(-[F;D1;H0:20])-[F;H0;D1;+0:21].[C:22]-[C:23]-[OH;D1;+0:24... | null | [] | null | null | 2 | HOUR | CF3(CF2)2OCF(CF3)CF2OCF(CF3)COF (120.69 g) was loaded into an autoclave and stirred under a nitrogen stream, and HO(CH2)3OCH(CH3)CH2OH (15.1 g) prepared in Example 2-3 was fed over 2 hours, while the temperature in the autoclave was maintained at 30° C. or below. Then, the reaction solution was stirred at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Trifluoro group.Trifluoro group.Tertiary halide.Tertiary halide.Primary alcohol.Primary alcohol | Trifluoro group.Trifluoro group.Trifluoro group.Trifluoro group.Trifluoro group.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Ester.Ester.Ether.Ether | null | null | null | Other | C(=O)(O)[O-].[Na+] | null | 2 | CC(CO)OCCCO.O=C(F)C(F)(OC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(F)(F)F>C(=O)(O)[O-].[Na+]>CC(COC(=O)C(F)(OC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(F)(F)F)OCCCOC(=O)C(F)(OC(F)(F)C(F)(OC(F)(F)C(F)(F)C(F)(F)F)C(F)(F)F)C(F)(F)F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9b383dcedcb34a41bc0685aba01455b8 | Cc1cc(C(C)(C)C)cc(C)c1S(=O)(=O)Cl.Cc1cc(C(C)(C)C)cc(C)c1S(=O)(=O)Cl>>Cc1cc(C(C)(C)C)cc(C)c1SSc1c(C)cc(C(C)(C)C)cc1C | CC1=C(C(=CC(=C1)C(C)(C)C)C)S(=O)(=O)Cl.CC1=C(C(=CC(=C1)C(C)(C)C)C)S(=O)(=O)Cl>>CC1=C(C(=CC(=C1)C(C)(C)C)C)SSC1=C(C=C(C=C1C)C(C)(C)C)C | O=[S:13](=O)(Cl)[c:12]1[c:2]([CH3:1])[cH:3][c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[cH:9][c:10]1[CH3:11].O=[S:14](=O)(Cl)[c:15]1[c:16]([CH3:17])[cH:18][c:19]([C:20]([CH3:21])([CH3:22])[CH3:23])[cH:24][c:25]1[CH3:26]>>[CH3:1][c:2]1[cH:3][c:4]([C:5]([CH3:6])([CH3:7])[CH3:8])[cH:9][c:10]([CH3:11])[c:12]1[S:13][S:14][c:15]1[c... | Cc1cc(C(C)(C)C)cc(C)c1S(=O)(=O)Cl.Cc1cc(C(C)(C)C)cc(C)c1S(=O)(=O)Cl | Cc1cc(C(C)(C)C)cc(C)c1SSc1c(C)cc(C(C)(C)C)cc1C | null | [Ti](Cl)(Cl)(Cl)Cl.[Zn].[Ti](Cl)(Cl)(Cl)Cl | O1CCCC1 | Miscellaneous | OtherReaction | 89bc08fe361ff61a489f484f20679a7df55a48107f2c39ffd1d09581fd50c810 | 9c42b3da034c86ee612727af954fc5bd394c43d40a029338ed887589dff65e6a | c1ccc(SSc2ccccc2)cc1 | Cl-[S;H0;D4;+0:1](=O)(=O)-[c:2](:[c:3]):[c:4].Cl-[S;H0;D4;+0:5](=O)(=O)-[c:6](:[c:7]):[c:8]>>[c:3]:[c:2](-[S;H0;D2;+0:1]-[S;H0;D2;+0:5]-[c:6](:[c:7]):[c:8]):[c:4] | 64.1 | [{"value": 64.1, "product": "CC1=C(C(=CC(=C1)C(C)(C)C)C)SSC1=C(C=C(C=C1C)C(C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | A two liter, three-neck flask, was obtained. A condenser with a drying tube, a thermometer, and a dropping funnel were each attached to the flask. Zinc dust (<10 micron, 43.6 g, 0.667 mol) and anhydrous tetrahydrofuran (400 mL) were added to the flask. The mixture was stirred and cooled on an ice-water bath and 58.6 ml... | 10.6084/m9.figshare.5104873.v1 | null | Sulfonyl halide.Sulfonyl halide | Disulfide | null | null | c1ccccc1.c1ccccc1 | Other | [Ti](Cl)(Cl)(Cl)Cl.[Zn].[Ti](Cl)(Cl)(Cl)Cl.O1CCCC1 | 60 | null | Cc1cc(C(C)(C)C)cc(C)c1S(=O)(=O)Cl.Cc1cc(C(C)(C)C)cc(C)c1S(=O)(=O)Cl>[Ti](Cl)(Cl)(Cl)Cl.[Zn].[Ti](Cl)(Cl)(Cl)Cl.O1CCCC1>Cc1cc(C(C)(C)C)cc(C)c1SSc1c(C)cc(C(C)(C)C)cc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-168c4fd7432548b4be25c5e932775b2c | FC(c1ccccc1)C(F)c1ccccc1>>FC(F)C(c1ccccc1)c1ccccc1 | FC(C(C1=CC=CC=C1)F)C1=CC=CC=C1.CC1=C(C(=CC(=C1)C(C)(C)C)C)S(F)(F)F.C1=CC=C(C=C1)[C@H]([C@H](C2=CC=CC=C2)O)O>>FC(C(C1=CC=CC=C1)C1=CC=CC=C1)F | [F:1][CH:2]([CH:4]([F:3])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1>>[F:1][CH:2]([F:3])[CH:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1 | FC(c1ccccc1)C(F)c1ccccc1 | FC(F)C(c1ccccc1)c1ccccc1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 33f5eee389135328e4ea80739281a0fec05a7ae4bbeb419b986075f2c964da81 | 715caf9c0ed0a006b1bedb353e5a492fd2cef4b9382daa4b0a254715d87abe0a | c1ccc(Cc2ccccc2)cc1 | [F;D1;H0:1]-[CH;D3;+0:2](-[CH;D3;+0:3](-[F;H0;D1;+0:4])-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12]>>[F;D1;H0:1]-[CH;D3;+0:2](-[F;H0;D1;+0:4])-[CH;D3;+0:3](-[c:5](:[c:6]):[c:7])-[c;H0;D3;+0:8](:[c:9]:[c:10]):[c:11]:[c:12] | 0.03 | [{"value": 0.03, "product": "FC(C(C1=CC=CC=C1)C1=CC=CC=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | In a 15 mL fluoropolymer flask, 2,6-dimethyl-4-tert-butylphenylsulfur trifluoride (0.625 g, 2.5 mmol) was dissolved in 5 mL of anhydrous CH2Cl2. A solution of meso-1,2-diphenyl-1,2-ethanediol (0.214 g, 1.0 mmol) in 5 mL of anhydrous CH2Cl2 was added to the above stirred solution at room temperature. After 3 hours, C12H... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide | Secondary halide.Secondary halide | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | null | C(Cl)Cl | null | 3 | FC(c1ccccc1)C(F)c1ccccc1>C(Cl)Cl>FC(F)C(c1ccccc1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da4e90e4acbe4d3ca8e30de0142f42ff | O=C(Cl)c1ccccc1.O=C(Nc1ccn([C@@H]2OC[C@@H](O)[C@@H](O)[C@H]2O)c(=O)n1)c1ccccc1>>O=C(Nc1ccn([C@@H]2OC[C@@H](O)[C@@H](O)[C@H]2OC(=O)c2ccccc2)c(=O)n1)c1ccccc1 | C(C1=CC=CC=C1)(=O)NC1=NC(N(C=C1)[C@H]1[C@H](O)[C@H](O)[C@H](O)CO1)=O.C(=O)(C1=CC=CC=C1)Cl.C(CC)O>>C(C1=CC=CC=C1)(=O)NC1=NC(N(C=C1)[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@H](O)[C@H](O)CO1)=O | Cl[C:17](=[O:18])[c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1.[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][n:7]([C@@H:8]2[O:9][CH2:10][C@@H:11]([OH:12])[C@@H:13]([OH:14])[C@H:15]2[OH:16])[c:25](=[O:26])[n:27]1)[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][n:7]([C@@H:8]2[O:9][CH2:10][C@@H:11](... | O=C(Cl)c1ccccc1.O=C(Nc1ccn([C@@H]2OC[C@@H](O)[C@@H](O)[C@H]2O)c(=O)n1)c1ccccc1 | O=C(Nc1ccn([C@@H]2OC[C@@H](O)[C@@H](O)[C@H]2OC(=O)c2ccccc2)c(=O)n1)c1ccccc1 | null | null | N1=CC=CC=C1.CN(C=O)C | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | O=C(Nc1ccn([C@@H]2OCCC[C@H]2OC(=O)c2ccccc2)c(=O)n1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]-[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]>>[#8:6]-[C:7]-[C:8](-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:10] | null | [] | 124 | CELSIUS | 8 | HOUR | 54.0 g (0.155 mol) of N4-benzoyl-1-(β-D-ribopyranosyl)cytosine 1 were dissolved in 830 ml of dimethylformamide (DMF) and 1.5 l of pyridine (both solvents dried and stored over molecular sieve 3 Å) with warming to 124° C. 23.0 g (0.163 mol; 1.05 eq.) of BzCl, dissolved in 210 ml of pyridine, were added dropwise at −58° ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | c1cncnc1.C1CCOCC1.c1ccccc1.c1ccccc1 | HCl | N1=CC=CC=C1.CN(C=O)C | 124 | 8 | O=C(Cl)c1ccccc1.O=C(Nc1ccn([C@@H]2OC[C@@H](O)[C@@H](O)[C@H]2O)c(=O)n1)c1ccccc1>N1=CC=CC=C1.CN(C=O)C>O=C(Nc1ccn([C@@H]2OC[C@@H](O)[C@@H](O)[C@H]2OC(=O)c2ccccc2)c(=O)n1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-97d2f9493a204b48a562afb3c9143e01 | O=C(Cl)c1ccccc1.O=C(c1ccccc1)N(C(=O)c1ccccc1)c1ncnc2c1ncn2[C@@H]1OC[C@@H](O)[C@@H](O)[C@H]1O>>O=C(O[C@@H]1[C@H](O)[C@H](O)CO[C@H]1n1cnc2c(N(C(=O)c3ccccc3)C(=O)c3ccccc3)ncnc21)c1ccccc1 | C(C1=CC=CC=C1)(=O)N(C1=C2N=CN(C2=NC=N1)[C@H]1[C@H](O)[C@H](O)[C@H](O)CO1)C(C1=CC=CC=C1)=O.C(=O)(C1=CC=CC=C1)Cl>>C(C1=CC=CC=C1)(=O)N(C1=C2N=CN(C2=NC=N1)[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@H](O)[C@H](O)CO1)C(C1=CC=CC=C1)=O | Cl[C:2](=[O:1])[c:38]1[cH:39][cH:40][cH:41][cH:42][cH:43]1.[OH:3][C@@H:4]1[C@H:5]([OH:6])[C@H:7]([OH:8])[CH2:9][O:10][C@H:11]1[n:12]1[cH:13][n:14][c:15]2[c:16]([N:17]([C:18](=[O:19])[c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[C:26](=[O:27])[c:28]3[cH:29][cH:30][cH:31][cH:32][cH:33]3)[n:34][cH:35][n:36][c:37]12>>[O:1]=... | O=C(Cl)c1ccccc1.O=C(c1ccccc1)N(C(=O)c1ccccc1)c1ncnc2c1ncn2[C@@H]1OC[C@@H](O)[C@@H](O)[C@H]1O | O=C(O[C@@H]1[C@H](O)[C@H](O)CO[C@H]1n1cnc2c(N(C(=O)c3ccccc3)C(=O)c3ccccc3)ncnc21)c1ccccc1 | null | CN(C)C=1C=CN=CC1 | N1=CC=CC=C1.C(Cl)Cl | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | O=C(O[C@@H]1CCCO[C@H]1n1cnc2c(N(C(=O)c3ccccc3)C(=O)c3ccccc3)ncnc21)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]-[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]>>[#8:6]-[C:7]-[C:8](-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:10] | 72.1 | [{"value": 72.1, "product": "C(C1=CC=CC=C1)(=O)N(C1=C2N=CN(C2=NC=N1)[C@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@H](O)[C@H](O)CO1)C(C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -88.5 | CELSIUS | 60 | HOUR | 26.4 g (55,5 mmol) of 3 were dissolved in 550 ml of anhydrous CH2Cl2 and 55 ml of pyridine (in each case stored over a molecular sieve) under an N2 atmosphere, treated with 0.73 g (5.55 mmol; 0.1 eq.) of DMAP and cooled to −87 to −90° C. 8.58 g (61 mmol; 1.1 eq.) of BzCl in 14 ml of pyridine were added dropwise in the ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | C1CCOCC1.c1ccccc1.c1ccccc1.c1ncnc2[nH]cnc12.c1ccccc1 | HCl | CN(C)C=1C=CN=CC1.N1=CC=CC=C1.C(Cl)Cl | -88.5 | 60 | O=C(Cl)c1ccccc1.O=C(c1ccccc1)N(C(=O)c1ccccc1)c1ncnc2c1ncn2[C@@H]1OC[C@@H](O)[C@@H](O)[C@H]1O>CN(C)C=1C=CN=CC1.N1=CC=CC=C1.C(Cl)Cl>O=C(O[C@@H]1[C@H](O)[C@H](O)CO[C@H]1n1cnc2c(N(C(=O)c3ccccc3)C(=O)c3ccccc3)ncnc21)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-74d1b8c5c2d54549b4a2b033dc7f78d5 | O=C(Cl)c1ccccc1.O=C1c2ccccc2C(=O)N1CCc1cn([C@@H]2OC[C@@H](O)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O>>O=C(O[C@@H]1[C@H](O)[C@H](O)CO[C@H]1n1cc(CCN2C(=O)c3ccccc3C2=O)c(=O)[nH]c1=O)c1ccccc1 | [Cl-].[NH4+].C1(C=2C(C(N1CCC=1C(NC(N(C1)[C@H]1[C@H](O)[C@H](O)[C@H](O)CO1)=O)=O)=O)=CC=CC2)=O.C(C1=CC=CC=C1)(=O)Cl>>C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](OC[C@H]([C@H]1O)O)N1C(=O)NC(=O)C(=C1)CCN1C(C=2C(C1=O)=CC=CC2)=O | Cl[C:2](=[O:1])[c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1.[OH:3][C@@H:4]1[C@H:5]([OH:6])[C@H:7]([OH:8])[CH2:9][O:10][C@H:11]1[n:12]1[cH:13][c:14]([CH2:15][CH2:16][N:17]2[C:18](=[O:19])[c:20]3[cH:21][cH:22][cH:23][cH:24][c:25]3[C:26]2=[O:27])[c:28](=[O:29])[nH:30][c:31]1=[O:32]>>[O:1]=[C:2]([O:3][C@@H:4]1[C@H:5]([OH:6]... | O=C(Cl)c1ccccc1.O=C1c2ccccc2C(=O)N1CCc1cn([C@@H]2OC[C@@H](O)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O | O=C(O[C@@H]1[C@H](O)[C@H](O)CO[C@H]1n1cc(CCN2C(=O)c3ccccc3C2=O)c(=O)[nH]c1=O)c1ccccc1 | null | null | N1=CC=CC=C1.ClCCl | Acylation | Schotten-Baumann to ester | 27b76e29491fa7db5375755e15223de884a194f57a493147db0b5495ea981908 | d47ab90ace9b5dcd818151c10aae400dcf599f5a3476072b8dfedc474e97c335 | O=C(O[C@@H]1CCCO[C@H]1n1cc(CCN2C(=O)c3ccccc3C2=O)c(=O)[nH]c1=O)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[#8:6]-[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]>>[#8:6]-[C:7]-[C:8](-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:10] | 60,597.3 | [{"value": 60.0, "product": "C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](OC[C@H]([C@H]1O)O)N1C(=O)NC(=O)C(=C1)CCN1C(C=2C(C1=O)=CC=CC2)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 60597.3, "product": "C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](OC[C@H]([C@H]1O)O)N1C(=O)NC(=O)C(=C1)CCN1C(C=2C(C1=O)=CC=CC2)=O", "details": "CAL... | -70 | CELSIUS | 35 | MINUTE | 10.6 g (0.025 mmol) of 5-(2-phtalimidoethyl)-1-(β-D-ribopyranosyl)uracil were dissolved in 20 ml of pyridine in a heated and argon-flushed 1 l four-necked flask and mixed with 200 ml of dichloromethane. The mixture was cooled to −70° C., 3.82 ml (0.033 mmol) of benzoyl chloride in 5 ml of pyridine and 20 ml of dichloro... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary alcohol | Ester | null | null | C1CCOCC1.c1cncnc1.c1ccc2c(c1)C[NH]C2.c1ccccc1 | HCl | N1=CC=CC=C1.ClCCl | -70 | 0.583333 | O=C(Cl)c1ccccc1.O=C1c2ccccc2C(=O)N1CCc1cn([C@@H]2OC[C@@H](O)[C@@H](O)[C@H]2O)c(=O)[nH]c1=O>N1=CC=CC=C1.ClCCl>O=C(O[C@@H]1[C@H](O)[C@H](O)CO[C@H]1n1cc(CCN2C(=O)c3ccccc3C2=O)c(=O)[nH]c1=O)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e68a2667e8044979cef6c0524dbcd71 | COc1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1OC>>COc1ccc(NCCc2ccc(C(F)(F)F)cc2)cc1OC | COC=1C=C(C=CC1OC)NC(CC1=CC=C(C=C1)C(F)(F)F)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.Cl>>COC=1C=C(C=CC1OC)NCCC1=CC=C(C=C1)C(F)(F)F | O=[C:8]([NH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:21]([O:22][CH3:23])[cH:20]1)[CH2:9][c:10]1[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]2)[cH:20][c:21]1[O:22][CH3:23] | COc1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1OC | COc1ccc(NCCc2ccc(C(F)(F)F)cc2)cc1OC | null | null | C1CCOC1 | Reduction | Reduction of secondary amides to amines | 85b757f1833edc9e5c6365ee6b904683f414e7b9a5f9bfcfd7addca401447058 | ab40188eef2f825df7003af0ffae31d0ce53d126542122535627d3d354cbc9fe | c1ccc(CCNc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[#7:2]-[c:3])-[C:4]-[c:5]>>[c:5]-[C:4]-[CH2;D2;+0:1]-[#7:2]-[c:3] | 24.5 | [{"value": 24.0, "product": "COC=1C=C(C=CC1OC)NCCC1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 24.5, "product": "COC=1C=C(C=CC1OC)NCCC1=CC=C(C=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | A mixture of 3 g (8.8 mmol) N-(3,4-Dimethoxy-phenyl)-2-(4-trifluoromethyl-phenyl)-acetamide and 1 g (26.3 mmol) LiAlH4 in 100 mL THF was stirred for 1 h at room temperature. Water and HCl aq. was added and the mixture was extracted with ethyl acetate. The combined organic phases were washed with water, dried with MgSO4... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | null | null | null | c1ccccc1.c1ccccc1 | Other | C1CCOC1 | null | 1 | COc1ccc(NC(=O)Cc2ccc(C(F)(F)F)cc2)cc1OC>C1CCOC1>COc1ccc(NCCc2ccc(C(F)(F)F)cc2)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b788071888c243319146f7e8d516f378 | COc1ccc(NCCc2ccc(C(F)(F)F)cc2)cc1OC.O=C(O)C(C(=O)OCc1ccccc1)c1ccccc1>>COc1ccc(N(CCc2ccc(C(F)(F)F)cc2)C(=O)C(C(=O)OCc2ccccc2)c2ccccc2)cc1OC | COC=1C=C(C=CC1OC)NCCC1=CC=C(C=C1)C(F)(F)F.C(C1=CC=CC=C1)OC(C(C(=O)O)C1=CC=CC=C1)=O.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.[B-](F)(F)(F)F.CCN(CC)CC>>C(C1=CC=CC=C1)OC(C(C(=O)N(CCC1=CC=C(C=C1)C(F)(F)F)C1=CC(=C(C=C1)OC)OC)C1=CC=CC=C1)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]2)[cH:39][c:40]1[O:41][CH3:42].O[C:20](=[O:21])[CH:22]([C:23](=[O:24])[O:25][CH2:26][c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1)[c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1>>[CH3:1][O:2][c:3]1[c... | COc1ccc(NCCc2ccc(C(F)(F)F)cc2)cc1OC.O=C(O)C(C(=O)OCc1ccccc1)c1ccccc1 | COc1ccc(N(CCc2ccc(C(F)(F)F)cc2)C(=O)C(C(=O)OCc2ccccc2)c2ccccc2)cc1OC | null | null | CN(C)C=O | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(OCc1ccccc1)C(C(=O)N(CCc1ccccc1)c1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8].[C:9]-[C:10]-[NH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[C:8]-[#8:7]-[C:5](=[O;D1;H0:6])-[C:3](-[c:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:11](-[C:10]-[C:9])-[c:12](:[c:13]):[c:14] | 29 | [{"value": 29.0, "product": "C(C1=CC=CC=C1)OC(C(C(=O)N(CCC1=CC=C(C=C1)C(F)(F)F)C1=CC(=C(C=C1)OC)OC)C1=CC=CC=C1)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 28.9, "product": "C(C1=CC=CC=C1)OC(C(C(=O)N(CCC1=CC=C(C=C1)C(F)(F)F)C1=CC(=C(C=C1)OC)OC)C1=CC=CC=C1)=O", "details": "CALCULATEDPERCENTYIELD", "is... | null | null | 16 | HOUR | A mixture of 0.7 g (2.1 mmol) (3,4-Dimethoxy-phenyl)-[2-(4-trifluoromethyl-phenyl)-ethyl]-amine, 0.58 g (2.1 mmol) 2-phenyl-malonic acid monobenzylester (commercially available), 0.83 g (2.5 mmol) TBTU and 0.43 g (4.3 mmol) NEt3 in 15 mL DMF was stirred at room temperature for 16 h. After evaporation to dryness the res... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | null | 16 | COc1ccc(NCCc2ccc(C(F)(F)F)cc2)cc1OC.O=C(O)C(C(=O)OCc1ccccc1)c1ccccc1>CN(C)C=O>COc1ccc(N(CCc2ccc(C(F)(F)F)cc2)C(=O)C(C(=O)OCc2ccccc2)c2ccccc2)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-42b4a92494f34c55aa383bde8206dcfe | COc1ccc(N(CCc2ccc(C(F)(F)F)cc2)C(=O)C(C(=O)OCc2ccccc2)c2ccccc2)cc1OC>>COc1ccc(N(CCc2ccc(C(F)(F)F)cc2)C(=O)C(C(=O)O)c2ccccc2)cc1OC | C(C1=CC=CC=C1)OC(C(C(=O)N(CCC1=CC=C(C=C1)C(F)(F)F)C1=CC(=C(C=C1)OC)OC)C1=CC=CC=C1)=O>>COC=1C=C(C=CC1OC)N(C(C(C(=O)O)C1=CC=CC=C1)=O)CCC1=CC=C(C=C1)C(F)(F)F | c1ccc(C[O:25][C:23]([CH:22]([C:20]([N:7]([c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[c:33]([O:34][CH3:35])[cH:32]2)[CH2:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([C:14]([F:15])([F:16])[F:17])[cH:18][cH:19]2)=[O:21])[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)=[O:24])cc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH2:8][CH2:9][c:... | COc1ccc(N(CCc2ccc(C(F)(F)F)cc2)C(=O)C(C(=O)OCc2ccccc2)c2ccccc2)cc1OC | COc1ccc(N(CCc2ccc(C(F)(F)F)cc2)C(=O)C(C(=O)O)c2ccccc2)cc1OC | null | [Pd] | C(C)(=O)O.C(C)(=O)OCC | Deprotection | Ester saponification (alkyl deprotection) | 86a971d3e4f88009ab4c98512e9f1deb51b2f0ce5cbd068cc61ae878c1e58e2a | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=C(Cc1ccccc1)N(CCc1ccccc1)c1ccccc1 | [#7:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](=[O;D1;H0:6])-[O;H0;D2;+0:7]-C-c1:c:c:c:c:c:1>>[#7:1]-[C:2](=[O;D1;H0:3])-[C:4]-[C:5](=[O;D1;H0:6])-[OH;D1;+0:7] | null | [] | null | null | null | null | 0.35 g (0.62 mmol) N-(3,4-Dimethoxy-phenyl)-2-phenyl-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-malonamic acid benzyl ester in 20 mL ethyl acetate and 0.37 mL acetic acid was hydrogenated over Pd/C with atmospheric pressure of H2 for 16 h at room temperature. The catalyst was filtered off and the and the filtrate evaporate... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | c1ccccc1 | null | c1ccccc1.c1ccccc1.c1ccccc1 | Other | [Pd].C(C)(=O)O.C(C)(=O)OCC | null | null | COc1ccc(N(CCc2ccc(C(F)(F)F)cc2)C(=O)C(C(=O)OCc2ccccc2)c2ccccc2)cc1OC>[Pd].C(C)(=O)O.C(C)(=O)OCC>COc1ccc(N(CCc2ccc(C(F)(F)F)cc2)C(=O)C(C(=O)O)c2ccccc2)cc1OC |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4b9d3f93ebc54ec0bf7376c8f134501f | CN.COc1ccc(N(CCc2ccc(C(F)(F)F)cc2)C(=O)C(C(=O)O)c2ccccc2)cc1OC>>CNC(=O)C(C(=O)N(CCc1ccc(C(F)(F)F)cc1)c1ccc(OC)c(OC)c1)c1ccccc1 | COC=1C=C(C=CC1OC)N(C(C(C(=O)O)C1=CC=CC=C1)=O)CCC1=CC=C(C=C1)C(F)(F)F.CN.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.[B-](F)(F)(F)F.N1=CC=CC=C1>>COC=1C=C(C=CC1OC)N(C(C(C(=O)NC)C1=CC=CC=C1)=O)CCC1=CC=C(C=C1)C(F)(F)F | [CH3:1][NH2:2].O[C:3](=[O:4])[CH:5]([C:6](=[O:7])[N:8]([CH2:9][CH2:10][c:11]1[cH:12][cH:13][c:14]([C:15]([F:16])([F:17])[F:18])[cH:19][cH:20]1)[c:21]1[cH:22][cH:23][c:24]([O:25][CH3:26])[c:27]([O:28][CH3:29])[cH:30]1)[c:31]1[cH:32][cH:33][cH:34][cH:35][cH:36]1>>[CH3:1][NH:2][C:3](=[O:4])[CH:5]([C:6](=[O:7])[N:8]([CH2:9... | CN.COc1ccc(N(CCc2ccc(C(F)(F)F)cc2)C(=O)C(C(=O)O)c2ccccc2)cc1OC | CNC(=O)C(C(=O)N(CCc1ccc(C(F)(F)F)cc1)c1ccc(OC)c(OC)c1)c1ccccc1 | null | null | CN(C)C=O | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(Cc1ccccc1)N(CCc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5](=[O;D1;H0:6])-[#7:7](-[C:8])-[c:9].[C;D1;H3:10]-[NH2;D1;+0:11]>>[C:8]-[#7:7](-[c:9])-[C:5](=[O;D1;H0:6])-[C:3](-[c:4])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C;D1;H3:10] | 16.3 | [{"value": 16.0, "product": "COC=1C=C(C=CC1OC)N(C(C(C(=O)NC)C1=CC=CC=C1)=O)CCC1=CC=C(C=C1)C(F)(F)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 16.3, "product": "COC=1C=C(C=CC1OC)N(C(C(C(=O)NC)C1=CC=CC=C1)=O)CCC1=CC=C(C=C1)C(F)(F)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | A mixture of 16.2 mg (0.033 mmol) N-(3,4-Dimethoxy-phenyl)-2-phenyl-N-[2-(4-trifluoromethyl-phenyl)-ethyl]-malonamic acid, 15.5 mg (0.049 mmol) methylamine (commercially available), 13.8 mg (0.043 mmol) TBTU and 7.8 mg (0.09 mmol) pyridine in 2 mL DMF was shaken for 4 h at room temperature. The mixture was evaporated t... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | null | 4 | CN.COc1ccc(N(CCc2ccc(C(F)(F)F)cc2)C(=O)C(C(=O)O)c2ccccc2)cc1OC>CN(C)C=O>CNC(=O)C(C(=O)N(CCc1ccc(C(F)(F)F)cc1)c1ccc(OC)c(OC)c1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-34500abe57a04c3db6dfd547c5979406 | CN(C)C(=O)C(C(=O)O)c1ccccc1.COc1ccc(NCCc2ccc(OC)c(OC)c2)cc1>>COc1ccc(N(CCc2ccc(OC)c(OC)c2)C(=O)C(C(=O)N(C)C)c2ccccc2)cc1 | COC=1C=C(C=CC1OC)CCNC1=CC=C(C=C1)OC.COC=1C=C(C=CC1OC)CCNC1=CC=C(C=C1)OC.CN(C(C(C(=O)O)C1=CC=CC=C1)=O)C.CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>>COC=1C=C(C=CC1OC)CCN(C(C(C(=O)N(C)C)C1=CC=CC=C1)=O)C1=CC=C(C=C1)OC | O[C:20](=[O:21])[CH:22]([C:23](=[O:24])[N:25]([CH3:26])[CH3:27])[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([NH:7][CH2:8][CH2:9][c:10]2[cH:11][cH:12][c:13]([O:14][CH3:15])[c:16]([O:17][CH3:18])[cH:19]2)[cH:34][cH:35]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([N:7]([CH2:8][CH2:9][c:10]2[c... | CN(C)C(=O)C(C(=O)O)c1ccccc1.COc1ccc(NCCc2ccc(OC)c(OC)c2)cc1 | COc1ccc(N(CCc2ccc(OC)c(OC)c2)C(=O)C(C(=O)N(C)C)c2ccccc2)cc1 | null | null | CN(C)C=O | Acylation | Acylation of Nitrogen Nucleophiles by Carboxylic Acids | ac72df6259d5d7baee7abdbd4706ef4b4627f86ead9dc94f0cefcfcb37c21def | c5e4172490b2731ba9322b68af56376edadc31ce0bb9a3dfdea23a1817a852fd | O=C(Cc1ccccc1)N(CCc1ccccc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5](=[O;D1;H0:6])-[#7:7](-[C;D1;H3:8])-[C;D1;H3:9].[C:10]-[C:11]-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C:10]-[C:11]-[N;H0;D3;+0:12](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[c:4])-[C:5](=[O;D1;H0:6])-[#7:7](-[C;D1;H3:8])-[C;D1;H3:9])-[c:13](:[c:14]):[c:15] | 61 | [{"value": 61.0, "product": "COC=1C=C(C=CC1OC)CCN(C(C(C(=O)N(C)C)C1=CC=CC=C1)=O)C1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 48.7, "product": "COC=1C=C(C=CC1OC)CCN(C(C(C(=O)N(C)C)C1=CC=CC=C1)=O)C1=CC=C(C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 16 | HOUR | A mixture of 28.7 mg (0.1 mmol) [2-(3,4-Dimethoxy-phenyl)-ethyl]-(4-methoxy-phenyl)-amine (intermediate 2), 20.7 mg (0.1 mmol) N,N-Dimethyl-2-phenyl-malonamic acid (WO2000009481), 38.5 mg (0.12 mmol) TBTU and 38.7 mg (0.3 mmol) DIPEA in 3 mL DMF was stirred at room temperature for 16 h. The mixture was concentrated dil... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | CN(C)C=O | null | 16 | CN(C)C(=O)C(C(=O)O)c1ccccc1.COc1ccc(NCCc2ccc(OC)c(OC)c2)cc1>CN(C)C=O>COc1ccc(N(CCc2ccc(OC)c(OC)c2)C(=O)C(C(=O)N(C)C)c2ccccc2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a175a90011cb4823bf69fdab4ee0fdf5 | CCOC(=O)C(C)(C(=O)Cl)c1ccccc1.COc1ccc(NCCc2ccc(C(F)(F)F)cc2)cc1OC>>CCOC(=O)C(C)(C(=O)N(CCc1ccc(C(F)(F)F)cc1)c1ccc(OC)c(OC)c1)c1ccccc1 | COC=1C=C(C=CC1OC)NCCC1=CC=C(C=C1)C(F)(F)F.COC=1C=C(C=CC1OC)NCCC1=CC=C(C=C1)C(F)(F)F.C(C)OC(C(C)(C1=CC=CC=C1)C(=O)Cl)=O.C(C)N(CC)CC>>C(C)OC(C(C(=O)N(CCC1=CC=C(C=C1)C(F)(F)F)C1=CC(=C(C=C1)OC)OC)(C1=CC=CC=C1)C)=O | Cl[C:8]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[c:33]1[cH:34][cH:35][cH:36][cH:37][cH:38]1)=[O:9].[NH:10]([CH2:11][CH2:12][c:13]1[cH:14][cH:15][c:16]([C:17]([F:18])([F:19])[F:20])[cH:21][cH:22]1)[c:23]1[cH:24][cH:25][c:26]([O:27][CH3:28])[c:29]([O:30][CH3:31])[cH:32]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH... | CCOC(=O)C(C)(C(=O)Cl)c1ccccc1.COc1ccc(NCCc2ccc(C(F)(F)F)cc2)cc1OC | CCOC(=O)C(C)(C(=O)N(CCc1ccc(C(F)(F)F)cc1)c1ccc(OC)c(OC)c1)c1ccccc1 | null | null | null | Acylation | N-alkylation of secondary amines with alkyl halides | b92e0bfd3d683c1f2a209adfe70a67ad7cb0d87749eb59e8fe0cf1689bc291e0 | 96cb0a2fed10552c5770a45a2d6523b47ac3e38928b4a9c698d8577451182dcd | O=C(Cc1ccccc1)N(CCc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[c:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9].[C:10]-[C:11]-[NH;D2;+0:12]-[c:13](:[c:14]):[c:15]>>[C:10]-[C:11]-[N;H0;D3;+0:12](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])(-[c:5])-[C:6](=[O;D1;H0:7])-[#8:8]-[C:9])-[c:13](:[c:14]):[c:15] | 45 | [{"value": 45.0, "product": "C(C)OC(C(C(=O)N(CCC1=CC=C(C=C1)C(F)(F)F)C1=CC(=C(C=C1)OC)OC)(C1=CC=CC=C1)C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.0, "product": "C(C)OC(C(C(=O)N(CCC1=CC=C(C=C1)C(F)(F)F)C1=CC(=C(C=C1)OC)OC)(C1=CC=CC=C1)C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | null | null | 16 | HOUR | A mixture of 97.5 mg (0.3 mmol) (3,4-dimethoxy-phenyl)-[2-(4-trifluoromethyl-phenyl)-ethyl]-amine (intermediate 1), 101 mg (0.45 mmol) 2-chlorocarbonyl-2-phenyl-propionic acid ethyl ester (Journal of Organic Chemistry (1959), 24 109-10) and 121 mg (1.2 mmol) triethylamine 15 mL DCM was stirred for 16 h at room temperat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HCl | null | null | 16 | CCOC(=O)C(C)(C(=O)Cl)c1ccccc1.COc1ccc(NCCc2ccc(C(F)(F)F)cc2)cc1OC>>CCOC(=O)C(C)(C(=O)N(CCc1ccc(C(F)(F)F)cc1)c1ccc(OC)c(OC)c1)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8a3c4571d07c44b796fe00511e454f86 | COCCOCc1nc(C(F)(F)F)ccc1C(=O)O.O=C1C=C(Cl)CCC1>>COCCOCc1nc(C(F)(F)F)ccc1C(=O)OC1=CC(=O)CCC1 | C(C)(C)N(CC)C(C)C.ClC1=CC(CCC1)=O.COCCOCC1=C(C(=O)O)C=CC(=N1)C(F)(F)F.C1(=CC=CC=C1)C.C1(=CC=CC=C1)C>>COCCOCC1=NC(=CC=C1C(=O)OC1=CC(CCC1)=O)C(F)(F)F | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][c:7]1[n:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][c:16]1[C:17](=[O:18])[OH:19].Cl[C:20]1=[CH:21][C:22](=[O:23])[CH2:24][CH2:25][CH2:26]1>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][c:7]1[n:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][c:16]1[C:17](=[O:18])[O:19][C:20]1... | COCCOCc1nc(C(F)(F)F)ccc1C(=O)O.O=C1C=C(Cl)CCC1 | COCCOCc1nc(C(F)(F)F)ccc1C(=O)OC1=CC(=O)CCC1 | null | [Cl-].[Cl-].[Zn+2] | ClCCl.O | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | fcf8f2bb951391d4eca3e180ca1db9de221ab19064c43fbc3ee25d99eb3d4dbc | 83fa46670fde4697f2da46ad00486528b93f00a3ef192db8e938bfe22fc495ff | O=C1C=C(OC(=O)c2cccnc2)CCC1 | Cl-[C;H0;D3;+0:1]1=[C:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6]-[C:7]-1.[#7;a:8]:[c:9]:[c:10]-[C:11](=[O;D1;H0:12])-[OH;D1;+0:13]>>[#7;a:8]:[c:9]:[c:10]-[C:11](=[O;D1;H0:12])-[O;H0;D2;+0:13]-[C;H0;D3;+0:1]1=[C:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6]-[C:7]-1 | null | [] | null | null | null | null | To a mixture of 157 mg (1.15 mmol) of 3-chlorocyclohex-2-en-1-one, 16 mg (0.12 mmol) of ZnCl2, 324 mg (1.15 mmol) of 2-methoxyethoxymethyl-6-trifluoromethylnicotinic acid (preparation described in WO 2001094339) and 2 ml of toluene there are added dropwise, under a nitrogen atmosphere, over the course of 15 minutes, 16... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Carboxylic acid | Ester | C1=CCCCC1 | C1=CCCCC1 | c1ccncc1.C1=CCCCC1 | HCl | [Cl-].[Cl-].[Zn+2].ClCCl.O | null | null | COCCOCc1nc(C(F)(F)F)ccc1C(=O)O.O=C1C=C(Cl)CCC1>[Cl-].[Cl-].[Zn+2].ClCCl.O>COCCOCc1nc(C(F)(F)F)ccc1C(=O)OC1=CC(=O)CCC1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e08e1cbc6beb424492820e89b8e50368 | COCCOCc1nc(C(F)(F)F)ccc1C(=O)O.O=C1C=C(Cl)C2CCC1C2>>COCCOCc1nc(C(F)(F)F)ccc1C(=O)OC1=CC(=O)C2CCC1C2 | C1(=CC=CC=C1)C.ClC1=CC(C2CCC1C2)=O.COCCOCC1=C(C(=O)O)C=CC(=N1)C(F)(F)F.C(C)(C)N(CC)C(C)C>>COCCOCC1=NC(=CC=C1C(=O)OC1=CC(C2CCC1C2)=O)C(F)(F)F | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][c:7]1[n:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][c:16]1[C:17](=[O:18])[OH:19].Cl[C:20]1=[CH:21][C:22](=[O:23])[CH:24]2[CH2:25][CH2:26][CH:27]1[CH2:28]2>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][c:7]1[n:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][c:16]1[C:17](=[O:1... | COCCOCc1nc(C(F)(F)F)ccc1C(=O)O.O=C1C=C(Cl)C2CCC1C2 | COCCOCc1nc(C(F)(F)F)ccc1C(=O)OC1=CC(=O)C2CCC1C2 | null | [Cl-].[Cl-].[Zn+2] | ClCCl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b0cc2671c5188ff45d2dc8f6f4a2748058b058251e35db4909cb7151f9e28dbd | 83fa46670fde4697f2da46ad00486528b93f00a3ef192db8e938bfe22fc495ff | O=C(OC1=CC(=O)C2CCC1C2)c1cccnc1 | Cl-[C;H0;D3;+0:1]1=[C:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6]-[C:7]-1-[C:8].[#7;a:9]:[c:10]:[c:11]-[C:12](=[O;D1;H0:13])-[OH;D1;+0:14]>>[#7;a:9]:[c:10]:[c:11]-[C:12](=[O;D1;H0:13])-[O;H0;D2;+0:14]-[C;H0;D3;+0:1]1=[C:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6]-[C:7]-1-[C:8] | null | [] | null | null | null | null | A mixture of 200 mg (1.15 mmol) of 4-chlorobicyclo[3.2.1]oct-3-en-2-one, (Preparation Example P2) 16 mg (0.12 mmol) of ZnCl2, 324 mg (1.15 mmol) of 2-methoxyethoxymethyl-6 -trifluoromethylnicotinic acid, 166 mg (1.27 mmol) of diisopropylethylamine and 5 ml of toluene is stirred under a nitrogen atmosphere at room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Carboxylic acid | Ester | C1=CC2CCC(C1)C2 | C1=CC2CCC(C1)C2 | c1ccncc1.C1=CC2CCC(C1)C2 | HCl | [Cl-].[Cl-].[Zn+2].ClCCl | null | null | COCCOCc1nc(C(F)(F)F)ccc1C(=O)O.O=C1C=C(Cl)C2CCC1C2>[Cl-].[Cl-].[Zn+2].ClCCl>COCCOCc1nc(C(F)(F)F)ccc1C(=O)OC1=CC(=O)C2CCC1C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-409d008ed9254c7a90cc86e77c706786 | O=C(O)c1ccc(Cl)cc1.O=C1C=C(Cl)C2CCC1C2>>O=C(OC1=CC(=O)C2CCC1C2)c1ccc(Cl)cc1 | C1(=CC=CC=C1)C.ClC1=CC(C2CCC1C2)=O.ClC1=CC=C(C(=O)O)C=C1.C(C)(C)N(CC)C(C)C>>ClC1=CC=C(C=C1)C(=O)OC1=CC(C2CCC1C2)=O | [O:1]=[C:2]([OH:3])[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1.Cl[C:4]1=[CH:5][C:6](=[O:7])[CH:8]2[CH2:9][CH2:10][CH:11]1[CH2:12]2>>[O:1]=[C:2]([O:3][C:4]1=[CH:5][C:6](=[O:7])[CH:8]2[CH2:9][CH2:10][CH:11]1[CH2:12]2)[c:13]1[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]1 | O=C(O)c1ccc(Cl)cc1.O=C1C=C(Cl)C2CCC1C2 | O=C(OC1=CC(=O)C2CCC1C2)c1ccc(Cl)cc1 | null | [Cl-].[Cl-].[Zn+2] | ClCCl | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b0cc2671c5188ff45d2dc8f6f4a2748058b058251e35db4909cb7151f9e28dbd | 83fa46670fde4697f2da46ad00486528b93f00a3ef192db8e938bfe22fc495ff | O=C(OC1=CC(=O)C2CCC1C2)c1ccccc1 | Cl-[C;H0;D3;+0:1]1=[C:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6]-[C:7]-1-[C:8].[O;D1;H0:9]=[C:10](-[OH;D1;+0:11])-[c:12]>>[C:8]-[C:7]1-[C:6]-[C:5]-[C:3](=[O;D1;H0:4])-[C:2]=[C;H0;D3;+0:1]-1-[O;H0;D2;+0:11]-[C:10](=[O;D1;H0:9])-[c:12] | 84.9 | [{"value": 84.9, "product": "ClC1=CC=C(C=C1)C(=O)OC1=CC(C2CCC1C2)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A mixture of 500 mg of 4-chlorobicyclo[3.2.1]oct-3-en-2-one (Preparation Example P2), 440 mg of ZnCl2, 400 mg of 4-chlorobenzoic acid, 1.05 g of diisopropylethylamine and 5 ml of toluene is stirred at room temperature under a nitrogen atmosphere at reflux temperature for 6 hours. After cooling, the reaction mixture is ... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Carboxylic acid | Ester | C1=CC2CCC(C1)C2 | C1=CC2CCC(C1)C2 | C1=CC2CCC(C1)C2.c1ccccc1 | HCl | [Cl-].[Cl-].[Zn+2].ClCCl | null | null | O=C(O)c1ccc(Cl)cc1.O=C1C=C(Cl)C2CCC1C2>[Cl-].[Cl-].[Zn+2].ClCCl>O=C(OC1=CC(=O)C2CCC1C2)c1ccc(Cl)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-490092c910054855818fdd351ad58b33 | COCCOCc1nc(C(F)(F)F)ccc1C(=O)O.O=C1C=C(Br)C2CCC1C2>>COCCOCc1nc(C(F)(F)F)ccc1C(=O)OC1=CC(=O)C2CCC1C2 | COCCOCC1=C(C(=O)O)C=CC(=N1)C(F)(F)F.CCN(C(C)C)C(C)C.COCCOCC1=C(C(=O)O)C=CC(=N1)C(F)(F)F.CCN(C(C)C)C(C)C.BrC1=CC(C2CCC1C2)=O>>COCCOCC1=NC(=CC=C1C(=O)OC1=CC(C2CCC1C2)=O)C(F)(F)F | [CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][c:7]1[n:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][c:16]1[C:17](=[O:18])[OH:19].Br[C:20]1=[CH:21][C:22](=[O:23])[CH:24]2[CH2:25][CH2:26][CH:27]1[CH2:28]2>>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][c:7]1[n:8][c:9]([C:10]([F:11])([F:12])[F:13])[cH:14][cH:15][c:16]1[C:17](=[O:1... | COCCOCc1nc(C(F)(F)F)ccc1C(=O)O.O=C1C=C(Br)C2CCC1C2 | COCCOCc1nc(C(F)(F)F)ccc1C(=O)OC1=CC(=O)C2CCC1C2 | null | [Cl-].[Cl-].[Zn+2].[Cl-].[Cl-].[Zn+2] | ClC1=CC=CC=C1 | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | b0cc2671c5188ff45d2dc8f6f4a2748058b058251e35db4909cb7151f9e28dbd | 83fa46670fde4697f2da46ad00486528b93f00a3ef192db8e938bfe22fc495ff | O=C(OC1=CC(=O)C2CCC1C2)c1cccnc1 | Br-[C;H0;D3;+0:1]1=[C:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6]-[C:7]-1-[C:8].[#7;a:9]:[c:10]:[c:11]-[C:12](=[O;D1;H0:13])-[OH;D1;+0:14]>>[#7;a:9]:[c:10]:[c:11]-[C:12](=[O;D1;H0:13])-[O;H0;D2;+0:14]-[C;H0;D3;+0:1]1=[C:2]-[C:3](=[O;D1;H0:4])-[C:5]-[C:6]-[C:7]-1-[C:8] | null | [] | null | null | null | null | A mixture of 27 g of a 6.2% solution of 4-bromobicyclo[3.2.1]oct-3-en-2-one (Preparation Example P1) in chlorobenzene, 110 mg of ZnCl2, 2.34 g of 2-methoxyethoxymethyl-6-trifluoromethylnicotinic acid and 1.2 g of Hünig's base is stirred at room temperature under a nitrogen atmosphere until a dark-brown solution is form... | 10.6084/m9.figshare.5104873.v1 | null | Alkenyl halide.Carboxylic acid | Ester | C1=CC2CCC(C1)C2 | C1=CC2CCC(C1)C2 | c1ccncc1.C1=CC2CCC(C1)C2 | HBr | [Cl-].[Cl-].[Zn+2].[Cl-].[Cl-].[Zn+2].ClC1=CC=CC=C1 | null | null | COCCOCc1nc(C(F)(F)F)ccc1C(=O)O.O=C1C=C(Br)C2CCC1C2>[Cl-].[Cl-].[Zn+2].[Cl-].[Cl-].[Zn+2].ClC1=CC=CC=C1>COCCOCc1nc(C(F)(F)F)ccc1C(=O)OC1=CC(=O)C2CCC1C2 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a2addf944a834de8a9024e8dbef1406e | C[C@H]1C(S(=O)(=O)c2ccccc2)C=C(Sc2ccccc2)CC[C@H]1O[Si](C)(C)C>>C[C@H]1C=CC(Sc2ccccc2)=CC[C@H]1O | CO.CCN(CC)CC.C1(=CC=CC=C1)S(=O)(=O)C1[C@@H]([C@@H](CCC(=C1)SC1=CC=CC=C1)O[Si](C)(C)C)C.[Si](C)(C)(C)OS(=O)(=O)C(F)(F)F>>C[C@@H]1[C@@H](CC=C(C=C1)SC1=CC=CC=C1)O | C[Si](C)(C)[O:16][C@H:15]1[C@@H:2]([CH3:1])[CH:3](S(=O)(=O)c2ccccc2)[CH:4]=[C:5]([S:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[CH2:13][CH2:14]1>>[CH3:1][C@H:2]1[CH:3]=[CH:4][C:5]([S:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)=[CH:13][CH2:14][C@H:15]1[OH:16] | C[C@H]1C(S(=O)(=O)c2ccccc2)C=C(Sc2ccccc2)CC[C@H]1O[Si](C)(C)C | C[C@H]1C=CC(Sc2ccccc2)=CC[C@H]1O | null | null | C(Cl)Cl.CCOC(=O)C | Functional Group Interconversion | OtherReaction | c5a8179abb456fc1073dcc1b69f4dd6858023288e1c82295e0fa28ad8154fde5 | b6232982cc0a6eaeb0e19aa9e067e5a44b4ff6428382e09578f8d924ae232629 | C1=CC(Sc2ccccc2)=CCCC1 | C-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[C:3]-[CH2;D2;+0:4]-[C;H0;D3;+0:5](-[#16:6]-[c:7])=[CH;D2;+0:8]-[CH;D3;+0:9](-S(=O)(=O)-c2:c:c:c:c:c:2)-[C:10]-1-[C;D1;H3:11]>>[C;D1;H3:11]-[C:10]1-[CH;D2;+0:9]=[CH;D2;+0:8]-[C;H0;D3;+0:5](-[#16:6]-[c:7])=[CH;D2;+0:4]-[C:3]-[C:2]-1-[OH;D1;+0:1] | 86.8 | [{"value": 86.0, "product": "C[C@@H]1[C@@H](CC=C(C=C1)SC1=CC=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.8, "product": "C[C@@H]1[C@@H](CC=C(C=C1)SC1=CC=CC=C1)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 8 | HOUR | 22 or 23 (2.15 g, 4.81 mmol) was dissolved in dry methylene chloride (20 mL), and 4.0 mL of Et3N (28.7 mmol) was added at room temperature, followed by addition of 3.0 mL (16.6 mmol) of TMSOTf. This mixture was brought to reflux under N2, and stirred for 8 h until the starting material was consumed (monitored by TLC us... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Sulfone.Silyl protective group | Secondary alcohol.Monosulfide | C1=CCCCCC1.c1ccccc1 | C1=CCCCC=C1 | C1=CCCCC=C1.c1ccccc1 | HO- | C(Cl)Cl.CCOC(=O)C | 0 | 8 | C[C@H]1C(S(=O)(=O)c2ccccc2)C=C(Sc2ccccc2)CC[C@H]1O[Si](C)(C)C>C(Cl)Cl.CCOC(=O)C>C[C@H]1C=CC(Sc2ccccc2)=CC[C@H]1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-336aa01dbe29406f86a022344008d3f8 | CI.C[C@H]1C=CC(Sc2ccccc2)=CC[C@H]1O>>C[C@H]1C=CC(Sc2ccccc2)=C[C@H](C)[C@H]1O | C[C@@H]1[C@@H](CC=C(C=C1)SC1=CC=CC=C1)O.CI.[Li]CCCC>>C[C@@H]1[C@H]([C@H](C=CC(=C1)SC1=CC=CC=C1)C)O | I[CH3:15].[CH3:1][C@H:2]1[CH:3]=[CH:4][C:5]([S:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)=[CH:13][CH2:14][C@H:16]1[OH:17]>>[CH3:1][C@H:2]1[CH:3]=[CH:4][C:5]([S:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)=[CH:13][C@H:14]([CH3:15])[C@H:16]1[OH:17] | CI.C[C@H]1C=CC(Sc2ccccc2)=CC[C@H]1O | C[C@H]1C=CC(Sc2ccccc2)=C[C@H](C)[C@H]1O | null | null | C1CCOC1 | C-C Coupling | Methylation with MeI_secondary | 21b917c068b9b7d2a61c0af1aace99f1a5bedcf90946eeff3fd7449263787c71 | 410ec9b1cc243569e4ff568c248f0b402403802e002b4018f576af3f6960507b | C1=CC(Sc2ccccc2)=CCCC1 | I-[CH3;D1;+0:1].[#16:2]-[C:3]1=[C:4]-[CH2;D2;+0:5]-[C:6](-[O;D1;H1:7])-[C:8]-[C:9]=[C:10]-1>>[#16:2]-[C:3]1=[C:4]-[C@H;D3;+0:5](-[CH3;D1;+0:1])-[C:6](-[O;D1;H1:7])-[C:8]-[C:9]=[C:10]-1 | 70.1 | [{"value": 70.0, "product": "C[C@@H]1[C@H]([C@H](C=CC(=C1)SC1=CC=CC=C1)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 70.1, "product": "C[C@@H]1[C@H]([C@H](C=CC(=C1)SC1=CC=CC=C1)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | -100 | CELSIUS | 1 | HOUR | A solution of alcohol 29 (887 mg, 3.82 mmol) in THF (50 mL) was cooled to −78° C., and 3.20 mL of n-BuLi (2.5 M in hexanes, 8.00 mmol) was added dropwise. The mixture was slowly brought to −7° C. over 1 h, and stirred at this temperature for 10 min. It was then cooled to −100° C. in a THF-liquid N2 bath. To this cold d... | 10.6084/m9.figshare.5104873.v1 | null | null | null | C1=CCCCC=C1 | C1=CCCCC=C1 | C1=CCCCC=C1.c1ccccc1 | HI | C1CCOC1 | -100 | 1 | CI.C[C@H]1C=CC(Sc2ccccc2)=CC[C@H]1O>C1CCOC1>C[C@H]1C=CC(Sc2ccccc2)=C[C@H](C)[C@H]1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1c02daaec61d4b3cbef197317b0fd01b | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F.C[C@H]1C=CC(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O>>C[C@H]1C=CC(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C | CO.C1(=CC=CC=C1)S(=O)(=O)C1=C[C@@H]([C@H]([C@H](C=C1)C)O)C.N1=C(C=CC=C1C)C.[Si](C)(C)(C(C)(C)C)OS(=O)(=O)C(F)(F)F>>C1(=CC=CC=C1)S(=O)(=O)C1=C[C@@H]([C@H]([C@H](C=C1)C)O[Si](C)(C)C(C)(C)C)C | O=S(=O)(O[Si:20]([CH3:21])([CH3:22])[C:23]([CH3:24])([CH3:25])[CH3:26])C(F)(F)F.[CH3:1][C@H:2]1[CH:3]=[CH:4][C:5]([S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)=[CH:15][C@H:16]([CH3:17])[C@H:18]1[OH:19]>>[CH3:1][C@H:2]1[CH:3]=[CH:4][C:5]([S:6](=[O:7])(=[O:8])[c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)... | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F.C[C@H]1C=CC(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O | C[C@H]1C=CC(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 5538bfc5ecbe9cd9a5fd4ec1ef8ed524aca8f082f4aad29482d3c63cae96472f | 55a582b0275cf25a85be636ee06e566428dd16a5bf0128e091e139c3b4d668ec | O=S(=O)(C1=CCCCC=C1)c1ccccc1 | F-C(-F)(-F)-S(=O)(=O)-O-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[OH;D1;+0:8]-[C:9]1-[C:10]-[C:11]=[C:12]-[C:13]=[C:14]-[C:15]-1>>[C;D1;H3:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3])(-[O;H0;D2;+0:8]-[C:9]1-[C:10]-[C:11]=[C:12]-[C:13]=[C:14]-[C:15]-1)-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6... | 98 | [{"value": 98.0, "product": "C1(=CC=CC=C1)S(=O)(=O)C1=C[C@@H]([C@H]([C@H](C=C1)C)O[Si](C)(C)C(C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 97.8, "product": "C1(=CC=CC=C1)S(=O)(=O)C1=C[C@@H]([C@H]([C@H](C=C1)C)O[Si](C)(C)C(C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A solution of alcohol 32 (550 mg, 1.98 mmol) and 2,6-lutidine (0.34 mL, 2.97 mmol) in CH2Cl2 (20 mL) was cooled to −78° C., and 0.55 mL (2.39 mmol) of TBSOTf was added. The cold solution was stirred and allowed to warm to 0° C. over a 1 h. MeOH (40 μL, 1 mmol) was then added and the resulting mixture was concentrated v... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Secondary alcohol.TMS ether protective group | TMS ether protective group | null | null | C1=CCCCC=C1.c1ccccc1 | TfOH.HO- | C(Cl)Cl | 0 | null | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F.C[C@H]1C=CC(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O>C(Cl)Cl>C[C@H]1C=CC(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f7b1fcffd58148b790e375925e1c0e94 | CC=[N+]=CC.C[C@H]1C=CC(Sc2ccccc2)=CC[C@H]1O>>C[C@H]1C=CC(Sc2ccccc2)=C[C@H](CN(C)C)[C@H]1O | C(=O)(O)[O-].[Na+].[Li]CCCC.C[C@@H]1[C@@H](CC=C(C=C1)SC1=CC=CC=C1)O.[I-].CC=[N+]=CC>>CN(C)C[C@@H]1[C@H]([C@H](C=CC(=C1)SC1=CC=CC=C1)C)O | C[CH:15]=[N+:16]=[CH:17][CH3:18].[CH3:1][C@H:2]1[CH:3]=[CH:4][C:5]([S:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)=[CH:13][CH2:14][C@H:19]1[OH:20]>>[CH3:1][C@H:2]1[CH:3]=[CH:4][C:5]([S:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)=[CH:13][C@H:14]([CH2:15][N:16]([CH3:17])[CH3:18])[C@H:19]1[OH:20] | CC=[N+]=CC.C[C@H]1C=CC(Sc2ccccc2)=CC[C@H]1O | C[C@H]1C=CC(Sc2ccccc2)=C[C@H](CN(C)C)[C@H]1O | null | null | C(Cl)Cl.CO.C1CCOC1 | Functional Group Addition | OtherReaction | 1c8bd53765008786c2e459063d4bf8e8a6b2967c8a491a3b9823c42d8b3faebb | a5ecc0f9f40a26873e3f25b9146fa7daf7ef454ae1fed653ab37babf6624d21a | C1=CC(Sc2ccccc2)=CCCC1 | C-[CH;D2;+0:1]=[N+;H0;D2:2]=[CH;D2;+0:3]-[CH3;D1;+0:4].[#16:5]-[C:6]1=[C:7]-[CH2;D2;+0:8]-[C:9](-[O;D1;H1:10])-[C:11]-[C:12]=[C:13]-1>>[#16:5]-[C:6]1=[C:7]-[C@H;D3;+0:8](-[CH2;D2;+0:1]-[N;H0;D3;+0:2](-[CH3;D1;+0:3])-[CH3;D1;+0:4])-[C:9](-[O;D1;H1:10])-[C:11]-[C:12]=[C:13]-1 | 58 | [{"value": 58.0, "product": "CN(C)C[C@@H]1[C@H]([C@H](C=CC(=C1)SC1=CC=CC=C1)C)O", "details": "PERCENTYIELD", "is_desired": false}] | -7 | CELSIUS | 1 | HOUR | A solution of alcohol 29 (80 mg, 0.34 mmol) in THF (4 mL) was cooled to −78° C., and 0.30 mL of n-BuLi (2.5M in hexanes, 0.75 mmol) was added dropwise via syringe. This mixture was brought to −7° C. over 1 h, and stirred at −7° C. for 10 min, then cooled to −78° C., and transferred to a flask containing N,N-dimethylmet... | 10.6084/m9.figshare.5104873.v1 | null | null | Tertiary amine | C1=CCCCC=C1 | C1=CCCCC=C1 | C1=CCCCC=C1.c1ccccc1 | Other | C(Cl)Cl.CO.C1CCOC1 | -7 | 1 | CC=[N+]=CC.C[C@H]1C=CC(Sc2ccccc2)=CC[C@H]1O>C(Cl)Cl.CO.C1CCOC1>C[C@H]1C=CC(Sc2ccccc2)=C[C@H](CN(C)C)[C@H]1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b21ca584e8cd4b3989e87ac2851e83ab | C[C@H]1C=CC(Sc2ccccc2)=C[C@H](CN(C)C)[C@H]1O.O=C(OO)c1cccc(Cl)c1>>C=C1C=C(S(=O)(=O)c2ccccc2)C=C[C@H](C)[C@@H]1O | OS(=O)[O-].[Na+].CN(C)C[C@@H]1[C@H]([C@H](C=CC(=C1)SC1=CC=CC=C1)C)O.C1=CC(=CC(=C1)Cl)C(=O)OO>>C1(=CC=CC=C1)S(=O)(=O)C1=CC([C@H]([C@H](C=C1)C)O)=C | CN(C)[CH2:1][C@H:2]1[CH:3]=[C:4]([S:5][c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH:14]=[CH:15][C@H:16]([CH3:17])[C@@H:18]1[OH:19].OOC(c1cccc(Cl)c1)=[O:6]>>[CH2:1]=[C:2]1[CH:3]=[C:4]([S:5](=[O:6])(=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH:14]=[CH:15][C@H:16]([CH3:17])[C@@H:18]1[OH:19] | C[C@H]1C=CC(Sc2ccccc2)=C[C@H](CN(C)C)[C@H]1O.O=C(OO)c1cccc(Cl)c1 | C=C1C=C(S(=O)(=O)c2ccccc2)C=C[C@H](C)[C@@H]1O | null | null | C(Cl)Cl | Oxidation | OtherReaction | 4e73d8a6e53dce15b599fa81e988dc52b98d89f1f1c66213112ad885558686e7 | f575dc3da217eae1ac1d3f527627a065b02dc653aa7aedb45e854bbd5e8c558c | C=C1C=C(S(=O)(=O)c2ccccc2)C=CCC1 | C-N(-C)-[CH2;D2;+0:1]-[C@H;D3;+0:2]1-[C:3]=[C:4](-[S;H0;D2;+0:5]-[c:6](:[c:7]):[c:8])-[C:9]=[C:10]-[C:11]-[C:12]-1-[O;D1;H1:13].Cl-c1:c:c:c:c(-C(=[O;H0;D1;+0:14])-O-O):c:1>>[CH2;D1;+0:1]=[C;H0;D3;+0:2]1-[C:3]=[C:4](-[S;H0;D4;+0:5](=[O;D1;H0:15])(=[O;H0;D1;+0:14])-[c:6](:[c:7]):[c:8])-[C:9]=[C:10]-[C:11]-[C:12]-1-[O;D1;... | null | [] | null | null | 30 | MINUTE | To a solution of amine 34 (42 mg, 0.14 mmol) in CH2Cl2 (2 mL) was added 140 mg of m-CPBA (0.57 mmol based on 70% content). The mixture was stirred at room temperature for 30 min, then aqueous NaHSO3 was added, the resulting two layers were separated, and the aqueous phase was extracted with CH2Cl2 (3×3 mL). The combine... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Tertiary amine.Peroxide.Monosulfide | Sulfone.Vinyl | C1=CCCCC=C1.c1ccccc1 | C1=CCCCC=C1 | C1=CCCCC=C1.c1ccccc1 | HCl | C(Cl)Cl | null | 0.5 | C[C@H]1C=CC(Sc2ccccc2)=C[C@H](CN(C)C)[C@H]1O.O=C(OO)c1cccc(Cl)c1>C(Cl)Cl>C=C1C=C(S(=O)(=O)c2ccccc2)C=C[C@H](C)[C@@H]1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-86f49c24746b4b3a8725423ba5400fa9 | CC(C)(C)OO.C[C@H]1C=CC(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O>>C[C@@H]1[C@H](O)[C@@H](C)C=C(S(=O)(=O)c2ccccc2)[C@@H]2O[C@H]12 | C1(=CC=CC=C1)S(=O)(=O)C1=C[C@@H]([C@H]([C@H](C=C1)C)O)C.C(C)(C)(C)OO>>C1(=CC=CC=C1)S(=O)(=O)C1=C[C@@H]([C@H]([C@H]([C@H]2O[C@@H]12)C)O)C | CC(C)(C)O[OH:19].[CH3:1][C@@H:2]1[C@@H:3]([OH:4])[C@@H:5]([CH3:6])[CH:7]=[CH:18][C:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)=[CH:20]1>>[CH3:1][C@@H:2]1[C@H:3]([OH:4])[C@@H:5]([CH3:6])[CH:7]=[C:8]([S:9](=[O:10])(=[O:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][cH:17]2)[C@@H:18]2[O:19][C@H:20]12 | CC(C)(C)OO.C[C@H]1C=CC(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O | C[C@@H]1[C@H](O)[C@@H](C)C=C(S(=O)(=O)c2ccccc2)[C@@H]2O[C@H]12 | null | [C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo] | C1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | eea2dab1111e082cf7b8c07a2e45ffe4ee54f851a6b2dc0700e3bea011267548 | 42a03c3e3056d859131de561fc8292c06b2910df7e46ddbdd3187d6cec35220b | O=S(=O)(C1=CCCC[C@H]2O[C@@H]12)c1ccccc1 | C-C(-C)(-C)-O-[OH;D1;+0:1].[C;D1;H3:2]-[C:3]1-[C:4]-[C:5](-[C;D1;H3:6])-[CH;D2;+0:7]=[CH;D2;+0:8]-[C;H0;D3;+0:9](-[#16:10](=[O;D1;H0:11])(=[O;D1;H0:12])-[c:13])=[CH;D2;+0:14]-1>>[C;D1;H3:2]-[C:3]1-[C:4]-[C:5](-[C;D1;H3:6])-[CH;D2;+0:7]=[C;H0;D3;+0:9](-[#16:10](=[O;D1;H0:11])(=[O;D1;H0:12])-[c:13])-[C@@H;D3;+0:8]2-[O;H0... | 88 | [{"value": 88.0, "product": "C1(=CC=CC=C1)S(=O)(=O)C1=C[C@@H]([C@H]([C@H]([C@H]2O[C@@H]12)C)O)C", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | A suspension of dienyl sulfone 32 (67 mg, 0.24 mmol), molybdenum hexacarbonyl (3 mg, 0.01 mmol), and tert-butylhydroperoxide (74 μL of 5M solution in decane) in benzene (3 mL) was heated at 80° C. for 10 h. The reaction mixture was concentrated via rotary evaporation, purified by flash column chromatography (ethyl acet... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | Ether | C1=CCCCC=C1 | C1=C[C@@H]2O[C@@H]2CCC1 | c1ccccc1.C1=C[C@@H]2O[C@@H]2CCC1 | HO- | [C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].C1=CC=CC=C1 | 80 | null | CC(C)(C)OO.C[C@H]1C=CC(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].C1=CC=CC=C1>C[C@@H]1[C@H](O)[C@@H](C)C=C(S(=O)(=O)c2ccccc2)[C@@H]2O[C@H]12 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7062d2f0602944bcae3a395bd632b80a | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F.C[C@@H]1[C@H](O)[C@@H](C)C=C(S(=O)(=O)c2ccccc2)[C@@H]2O[C@H]12>>C[C@H]1[C@H]2O[C@H]2C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C | CO.C1(=CC=CC=C1)S(=O)(=O)C1=C[C@@H]([C@H]([C@H]([C@H]2O[C@@H]12)C)O)C.N1=C(C=CC=C1C)C.[Si](C)(C)(C(C)(C)C)OS(=O)(=O)C(F)(F)F>>C1(=CC=CC=C1)S(=O)(=O)C1=C[C@@H]([C@H]([C@H]([C@H]2O[C@@H]12)C)O[Si](C)(C)C(C)(C)C)C | O=S(=O)(O[Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27])C(F)(F)F.[CH3:1][C@H:2]1[C@H:3]2[O:4][C@H:5]2[C:6]([S:7](=[O:8])(=[O:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][cH:15]2)=[CH:16][C@H:17]([CH3:18])[C@H:19]1[OH:20]>>[CH3:1][C@H:2]1[C@H:3]2[O:4][C@H:5]2[C:6]([S:7](=[O:8])(=[O:9])[c:10]2[cH:11][cH:12][cH:1... | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F.C[C@@H]1[C@H](O)[C@@H](C)C=C(S(=O)(=O)c2ccccc2)[C@@H]2O[C@H]12 | C[C@H]1[C@H]2O[C@H]2C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 5538bfc5ecbe9cd9a5fd4ec1ef8ed524aca8f082f4aad29482d3c63cae96472f | 55a582b0275cf25a85be636ee06e566428dd16a5bf0128e091e139c3b4d668ec | O=S(=O)(C1=CCCC[C@H]2O[C@@H]12)c1ccccc1 | F-C(-F)(-F)-S(=O)(=O)-O-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]-[C:9](-[OH;D1;+0:10])-[C:11]-[C:12]=[C:13]>>[C:8]-[C:9](-[O;H0;D2;+0:10]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7])-[C:11]-[C:12]=[C:13] | 95.6 | [{"value": 95.0, "product": "C1(=CC=CC=C1)S(=O)(=O)C1=C[C@@H]([C@H]([C@H]([C@H]2O[C@@H]12)C)O[Si](C)(C)C(C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 95.6, "product": "C1(=CC=CC=C1)S(=O)(=O)C1=C[C@@H]([C@H]([C@H]([C@H]2O[C@@H]12)C)O[Si](C)(C)C(C)(C)C)C", "details": "CALCULATEDPERCENTYIELD", "is... | -78 | CELSIUS | null | null | A mixture of alcohol α36 (62 mg, 0.21 mmol) and 2,6-lutidine (50 μL, 0.43 mmol) in CH2Cl2 (2 mL) was cooled to −78° C., and 63 μL (0.27 mmol) of TBSOTf was added. The stirred cold solution was warmed to 0° C. over 5 h. MeOH (40 μL, 1 mmol) was then added to quench the excess TBSOTf. The resulting mixture was concentrat... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Secondary alcohol.TMS ether protective group | TMS ether protective group | null | null | C1=C[C@@H]2O[C@@H]2CCC1.c1ccccc1 | TfOH.HO- | C(Cl)Cl | -78 | null | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F.C[C@@H]1[C@H](O)[C@@H](C)C=C(S(=O)(=O)c2ccccc2)[C@@H]2O[C@H]12>C(Cl)Cl>C[C@H]1[C@H]2O[C@H]2C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-978d8844d75b40e69912f3415fd0a03e | C[C@H]1C=CC(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C>>C[C@H]1[C@H](O)[C@H](O)C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C | C1(=CC=CC=C1)S(=O)(=O)C1=C[C@@H]([C@H]([C@H](C=C1)C)O[Si](C)(C)C(C)(C)C)C.C[N+]1(CCOCC1)[O-].[O-]S(=O)(=S)[O-].[Na+].[Na+]>>C1(=CC=CC=C1)S(=O)(=O)C=1[C@H]([C@H]([C@@H]([C@@H]([C@H](C1)C)O[Si](C)(C)C(C)(C)C)C)O)O | [CH3:1][C@H:2]1[CH:3]=[CH:5][C:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)=[CH:17][C@H:18]([CH3:19])[C@H:20]1[O:21][Si:22]([CH3:23])([CH3:24])[C:25]([CH3:26])([CH3:27])[CH3:28]>>[CH3:1][C@H:2]1[C@H:3]([OH:4])[C@H:5]([OH:6])[C:7]([S:8](=[O:9])(=[O:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2... | C[C@H]1C=CC(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C | C[C@H]1[C@H](O)[C@H](O)C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C | null | O=[Os](=O)(=O)=O | O.CC(=O)C.C(C)(=O)OCC | Oxidation | Alkene to diol | 7e69a9bdf93826c76ddd41cc5796f4a45c5625e9ad9b7072dbd7eeda89cd597d | 4ce7d04b0dc7802a0fb0fdf6618787b32ab28eb210bbbb25767ced5b1fe9204d | O=S(=O)(C1=CCCCCC1)c1ccccc1 | [#16:1]-[C:2]1=[C:3]-[C:4]-[C:5]-[C:6](-[C;D1;H3:7])-[CH;D2;+0:8]=[CH;D2;+0:9]-1>>[#16:1]-[C:2]1=[C:3]-[C:4]-[C:5]-[C:6](-[C;D1;H3:7])-[C@H;D3;+0:8](-[O;D1;H1:10])-[C@@H;D3;+0:9]-1-[O;D1;H1:11] | 83 | [{"value": 83.0, "product": "C1(=CC=CC=C1)S(=O)(=O)C=1[C@H]([C@H]([C@@H]([C@@H]([C@H](C1)C)O[Si](C)(C)C(C)(C)C)C)O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 36 | HOUR | A mixture of dienyl sulfone 33 (45 mg, 0.11 mmol), OsO4 (2 mg, 0.0078 mmol), 4-methylmorpholine N-oxide (27 mg, 0.23 mmol) in acetone (0.5 mL) and H2O (0.5 mL) as co-solvent was stirred at room temperature for 36 h, then saturated aqueous Na2S2O3 (5 mL) was added, and stirred for 30 min. The reaction mixture was dilute... | 10.6084/m9.figshare.5104873.v1 | null | null | Secondary alcohol.Secondary alcohol | C1=CCCCC=C1 | C1=CCCCCC1 | C1=CCCCCC1.c1ccccc1 | Other | O=[Os](=O)(=O)=O.O.CC(=O)C.C(C)(=O)OCC | null | 36 | C[C@H]1C=CC(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C>O=[Os](=O)(=O)=O.O.CC(=O)C.C(C)(=O)OCC>C[C@H]1[C@H](O)[C@H](O)C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-7137800094964e29955ab14be3d26d96 | CC(=O)OC(C)=O.C[C@@H]1[C@H](O)CCC(Sc2ccccc2)=C[C@@H]1S(=O)(=O)c1ccccc1>>CC(=O)O[C@H]1CCC(=O)C[C@@H](S(=O)(=O)c2ccccc2)[C@H]1C | C1(=CC=CC=C1)S(=O)(=O)[C@@H]1[C@@H]([C@@H](CCC(=C1)SC1=CC=CC=C1)O)C.C(C)(=O)OC(C)=O.C(C)N(CC)CC.[I-].[Na+].Cl[Si](C)(C)C.O.C1(=CC=CC=C1)S(=O)(=O)[C@@H]1[C@@H]([C@@H](CCC(=C1)SC1=CC=CC=C1)O)C>>C1(=CC=CC=C1)S(=O)(=O)[C@H]1[C@H]([C@H](CCC(C1)=O)OC(C)=O)C | CC(O[C:2]([CH3:1])=[O:3])=[O:9].c1ccc(S[C:8]2=[CH:10][C@H:11]([S:12](=[O:13])(=[O:14])[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[C@H:21]([CH3:22])[C@H:5]([OH:4])[CH2:6][CH2:7]2)cc1>>[CH3:1][C:2](=[O:3])[O:4][C@H:5]1[CH2:6][CH2:7][C:8](=[O:9])[CH2:10][C@@H:11]([S:12](=[O:13])(=[O:14])[c:15]2[cH:16][cH:17][cH:18][cH:19... | CC(=O)OC(C)=O.C[C@@H]1[C@H](O)CCC(Sc2ccccc2)=C[C@@H]1S(=O)(=O)c1ccccc1 | CC(=O)O[C@H]1CCC(=O)C[C@@H](S(=O)(=O)c2ccccc2)[C@H]1C | null | Cl[Hg]Cl | ClCCl.C(C)#N | Acylation | OtherReaction | 8b047b910960ca5036329fbb60c10d38c50df9fd85dbfacaf84dc2f8c120600c | 295c5e035c2f8a1953383ce9322128b08edd510507adc4edb1b31e2c834ae9cf | O=C1CCCC[C@H](S(=O)(=O)c2ccccc2)C1 | C-C(=[O;H0;D1;+0:1])-O-[C;H0;D3;+0:2](-[C;D1;H3:3])=[O;D1;H0:4].[#16:5]-[C:6]1-[C:7]-[C:8](-[OH;D1;+0:9])-[C:10]-[C:11]-[C;H0;D3;+0:12](-S-c2:c:c:c:c:c:2)=[CH;D2;+0:13]-1>>[#16:5]-[C:6]1-[C:7]-[C:8](-[O;H0;D2;+0:9]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[O;D1;H0:4])-[C:10]-[C:11]-[C;H0;D3;+0:12](=[O;H0;D1;+0:1])-[CH2;D2;+0:13]-1 | 85 | [{"value": 85.0, "product": "C1(=CC=CC=C1)S(=O)(=O)[C@H]1[C@H]([C@H](CCC(C1)=O)OC(C)=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.9, "product": "C1(=CC=CC=C1)S(=O)(=O)[C@H]1[C@H]([C@H](CCC(C1)=O)OC(C)=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of 21 (4.63 g, 12.38 mmol) in dichloromethane (62 mL) was added acetic anhydride (1.40 mL, 14.9 mmol), triethylamine (2.61 mL, 18.6 mmol), and a catalytic amount of N,N-dimethylaminopyridine. The solution was stirred for 30 minutes at room temperature, diluted with dichloromethane (60 mL), washed with wat... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary alcohol.Monosulfide | Ketone.Ester | c1ccccc1.C1=CCCCCC1 | C1CCCCCC1 | C1CCCCCC1.c1ccccc1 | Other | Cl[Hg]Cl.ClCCl.C(C)#N | null | 0.5 | CC(=O)OC(C)=O.C[C@@H]1[C@H](O)CCC(Sc2ccccc2)=C[C@@H]1S(=O)(=O)c1ccccc1>Cl[Hg]Cl.ClCCl.C(C)#N>CC(=O)O[C@H]1CCC(=O)C[C@@H](S(=O)(=O)c2ccccc2)[C@H]1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-39222e8f250c4a279aec2e928411e88c | C[C@H]1[C@H]2O[C@H]2C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C>>C[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)C=C(S(=O)(=O)c2ccccc2)C[C@@H]1O | C1(=CC=CC=C1)S(=O)(=O)C1=C[C@@H]([C@H]([C@H]([C@H]2O[C@@H]12)C)O[Si](C)(C)C(C)(C)C)C.C1CCOC1.CC(C)C[AlH]CC(C)C>>C1(=CC=CC=C1)S(=O)(=O)C=1C[C@@H]([C@@H]([C@@H]([C@H](C1)C)O[Si](C)(C)C(C)(C)C)C)O | [CH3:1][C@@H:2]1[C@H:3]([O:4][Si:5]([CH3:6])([CH3:7])[C:8]([CH3:9])([CH3:10])[CH3:11])[C@@H:12]([CH3:13])[CH:14]=[C:15]([S:16](=[O:17])(=[O:18])[c:19]2[cH:20][cH:21][cH:22][cH:23][cH:24]2)[C@H:25]2[C@@H:26]1[O:27]2>>[CH3:1][C@@H:2]1[C@H:3]([O:4][Si:5]([CH3:6])([CH3:7])[C:8]([CH3:9])([CH3:10])[CH3:11])[C@@H:12]([CH3:13]... | C[C@H]1[C@H]2O[C@H]2C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C | C[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)C=C(S(=O)(=O)c2ccccc2)C[C@@H]1O | null | null | C1(=CC=CC=C1)C | Reduction | OtherReaction | 074bf371dcb142f3532dac755d4497500a2fbf5507a41d6c839926a966132f47 | 7198fae1b68de0a7b3cad42fd2e176cc1d426019158d5ea9d2333b476668381b | O=S(=O)(C1=CCCCCC1)c1ccccc1 | [#16:1]-[C:2]1=[C:3]-[C:4]-[C:5]-[C:6](-[C;D1;H3:7])-[C@H;D3;+0:8]2-[O;H0;D2;+0:9]-[C@@H;D3;+0:10]-1-2>>[#16:1]-[C:2]1=[C:3]-[C:4]-[C:5]-[C:6](-[C;D1;H3:7])-[C@@H;D3;+0:8](-[OH;D1;+0:9])-[CH2;D2;+0:10]-1 | 87.2 | [{"value": 85.0, "product": "C1(=CC=CC=C1)S(=O)(=O)C=1C[C@@H]([C@@H]([C@@H]([C@H](C1)C)O[Si](C)(C)C(C)(C)C)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 87.2, "product": "C1(=CC=CC=C1)S(=O)(=O)C=1C[C@@H]([C@@H]([C@@H]([C@H](C1)C)O[Si](C)(C)C(C)(C)C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desir... | -78 | CELSIUS | 3 | HOUR | Compound α37 (39 mg, 0.095 mmol) was dissolved in dry toluene (1.0 mL), and the temperature lowered to −78° C. To this cold solution was added THF (10 μL, 0.12 mmol), followed by DIBAL-H solution (0.20 mL of 1.55M in toluene) under nitrogen, and the reaction stirred magnetically at −78° C. for 3 hours. Upon completion,... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Secondary alcohol | C1=C[C@@H]2O[C@@H]2CCC1 | C1=CCCCCC1 | C1=CCCCCC1.c1ccccc1 | null | C1(=CC=CC=C1)C | -78 | 3 | C[C@H]1[C@H]2O[C@H]2C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C>C1(=CC=CC=C1)C>C[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)C=C(S(=O)(=O)c2ccccc2)C[C@@H]1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72bc74af69114b41ab0a74cdf3541e4c | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F.C[C@H]1[C@H](O)[C@H](O)C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C>>C[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C | C1(=CC=CC=C1)S(=O)(=O)C=1[C@H]([C@H]([C@@H]([C@@H]([C@H](C1)C)O[Si](C)(C)C(C)(C)C)C)O)O.N1=C(C=CC=C1C)C.CO.[Si](C)(C)(C(C)(C)C)OS(=O)(=O)C(F)(F)F>>C1(=CC=CC=C1)S(=O)(=O)C=1[C@H]([C@H]([C@@H]([C@@H]([C@H](C1)C)O[Si](C)(C)C(C)(C)C)C)O[Si](C)(C)C(C)(C)C)O | O=S(=O)(O[Si:5]([CH3:6])([CH3:7])[C:8]([CH3:9])([CH3:10])[CH3:11])C(F)(F)F.[CH3:1][C@H:2]1[C@H:3]([OH:4])[C@H:12]([OH:13])[C:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)=[CH:24][C@H:25]([CH3:26])[C@H:27]1[O:28][Si:29]([CH3:30])([CH3:31])[C:32]([CH3:33])([CH3:34])[CH3:35]>>[CH3:1][C@H:2]1[C@H... | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F.C[C@H]1[C@H](O)[C@H](O)C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C | C[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C | null | null | C(Cl)Cl | Functional Group Interconversion | OtherReaction | 5538bfc5ecbe9cd9a5fd4ec1ef8ed524aca8f082f4aad29482d3c63cae96472f | 55a582b0275cf25a85be636ee06e566428dd16a5bf0128e091e139c3b4d668ec | O=S(=O)(C1=CCCCCC1)c1ccccc1 | F-C(-F)(-F)-S(=O)(=O)-O-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7].[C:8]=[C:9]-[C:10]-[C:11](-[OH;D1;+0:12])-[C:13]>>[C:8]=[C:9]-[C:10]-[C:11](-[O;H0;D2;+0:12]-[Si;H0;D4;+0:1](-[C;D1;H3:2])(-[C;D1;H3:3])-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7])-[C:13] | 99.6 | [{"value": 99.0, "product": "C1(=CC=CC=C1)S(=O)(=O)C=1[C@H]([C@H]([C@@H]([C@@H]([C@H](C1)C)O[Si](C)(C)C(C)(C)C)C)O[Si](C)(C)C(C)(C)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.6, "product": "C1(=CC=CC=C1)S(=O)(=O)C=1[C@H]([C@H]([C@@H]([C@@H]([C@H](C1)C)O[Si](C)(C)C(C)(C)C)C)O[Si](C)(C)C(C)(C)C)O"... | -78 | CELSIUS | 2 | HOUR | Compound 39 (77 mg, 0.18 mmol) was dissolved in dry methylene chloride (2.0 mL), and cooled to −78° C. To this cold solution were added 2,6-lutidine (32 μL, 0.27 mmol), followed by TBSOTf (50 μL, 0.22 mmol) under nitrogen. After stirring for 2 h at −78° C. (the reaction was monitored by TLC until completionusing a mixt... | 10.6084/m9.figshare.5104873.v1 | null | Triflate.Secondary alcohol.TMS ether protective group | TMS ether protective group | null | null | C1=CCCCCC1.c1ccccc1 | TfOH.HO- | C(Cl)Cl | -78 | 2 | CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F.C[C@H]1[C@H](O)[C@H](O)C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C>C(Cl)Cl>C[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b1782a0af1a84ba9b389e90c07478f26 | CI.C[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C>>CO[C@@H]1C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@@H]1O[Si](C)(C)C(C)(C)C | O.C1(=CC=CC=C1)S(=O)(=O)C=1[C@H]([C@H]([C@@H]([C@@H]([C@H](C1)C)O[Si](C)(C)C(C)(C)C)C)O[Si](C)(C)C(C)(C)C)O.CI.[OH-].[K+]>>C1(=CC=CC=C1)S(=O)(=O)C1=C[C@@H]([C@H]([C@H]([C@@H]([C@@H]1OC)O[Si](C)(C)C(C)(C)C)C)O[Si](C)(C)C(C)(C)C)C | I[CH3:1].[OH:2][C@@H:3]1[C:4]([S:5](=[O:6])(=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)=[CH:14][C@H:15]([CH3:16])[C@@H:17]([O:18][Si:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[CH3:25])[C@@H:26]([CH3:27])[C@@H:28]1[O:29][Si:30]([CH3:31])([CH3:32])[C:33]([CH3:34])([CH3:35])[CH3:36]>>[CH3:1][O:2][C@@H:3]1[C:4... | CI.C[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C | CO[C@@H]1C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@@H]1O[Si](C)(C)C(C)(C)C | null | null | C(C)(=O)OCC.CCCCCC.CS(=O)C | Heteroatom Alkylation and Arylation | Williamson Ether Synthesis | 31ec8f945a35f4f87287620e27b68692ce42732551035fbac056df61d9acce14 | 08f7221cae607d413f579138dcaa6997bebcad2bbb42d2f1b3b2a2d886befb37 | O=S(=O)(C1=CCCCCC1)c1ccccc1 | I-[CH3;D1;+0:1].[#16:2]-[C:3](=[C:4]-[C:5])-[C:6](-[OH;D1;+0:7])-[C:8]>>[#16:2]-[C:3](=[C:4]-[C:5])-[C:6](-[O;H0;D2;+0:7]-[CH3;D1;+0:1])-[C:8] | 94 | [{"value": 94.0, "product": "C1(=CC=CC=C1)S(=O)(=O)C1=C[C@@H]([C@H]([C@H]([C@@H]([C@@H]1OC)O[Si](C)(C)C(C)(C)C)C)O[Si](C)(C)C(C)(C)C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 92.7, "product": "C1(=CC=CC=C1)S(=O)(=O)C1=C[C@@H]([C@H]([C@H]([C@@H]([C@@H]1OC)O[Si](C)(C)C(C)(C)C)C)O[Si](C)(C)C(C)(C)C)C"... | null | null | 5 | MINUTE | To a solution of compound 52 (75 mg, 0.14 mmol) and MeI (86 μL, 1.4 mmol) in DMSO (2.0 mL) was added powdered KOH (23 mg, 0.42 mmol) and the resulting mixture was stirred for 5 min (until no starting material was present by TLC, developed in 1:3 EA/hexanes) at room temperature. 5 mL of H2O was added, and extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ether | null | null | C1=CCCCCC1.c1ccccc1 | HI | C(C)(=O)OCC.CCCCCC.CS(=O)C | null | 0.083333 | CI.C[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@H]1O[Si](C)(C)C(C)(C)C>C(C)(=O)OCC.CCCCCC.CS(=O)C>CO[C@@H]1C(S(=O)(=O)c2ccccc2)=C[C@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@@H]1O[Si](C)(C)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-d87b75ced07142f3b235698e7c4c8744 | CC1C(O)CC=CC1S(=O)(=O)c1ccccc1>>C[C@H]1CCC(=O)C=C1S(=O)(=O)c1ccccc1 | [Li]C.[NH4+].[Cl-].[Li+].C[Si](C)(C)[N-][Si](C)(C)C.C1(=CC=CC=C1)S(=O)(=O)C1C=CCC(C1C)O>>C1(=CC=CC=C1)S(=O)(=O)C1=CC(CC[C@@H]1C)=O | [CH3:1][CH:2]1[CH:3]([OH:6])[CH2:4][CH:5]=[CH:7][CH:8]1[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][C@H:2]1[CH2:3][CH2:4][C:5](=[O:6])[CH:7]=[C:8]1[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | CC1C(O)CC=CC1S(=O)(=O)c1ccccc1 | C[C@H]1CCC(=O)C=C1S(=O)(=O)c1ccccc1 | null | null | CCOCC.C1CCOC1 | Miscellaneous | OtherReaction | 53cf4e2066676acec66f9f3f7a3a23d51f563226cdd6f5b0777cb107a8e9d680 | ef59ba7fad669d0d82c4daf03280dc0366c9a31cf6192836b4997e72f66f9d7c | O=C1C=C(S(=O)(=O)c2ccccc2)CCC1 | [C;D1;H3:1]-[CH;D3;+0:2]1-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[CH;D2;+0:6]=[CH;D2;+0:7]-[CH;D3;+0:8]-1-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12]>>[C;D1;H3:1]-[C@H;D3;+0:2]1-[CH2;D2;+0:3]-[C:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:4])-[CH;D2;+0:7]=[C;H0;D3;+0:8]-1-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12] | 92 | [{"value": 92.0, "product": "C1(=CC=CC=C1)S(=O)(=O)C1=CC(CC[C@@H]1C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | (1S, 55, 65)-5-Benzenesulfonyl-6-methylcyclohex-3-enol (22aMe). To a solution of epoxy-dienyl sulfone SS-9a (0.377 g, 1.6 mmol) in THF (10 mL) at −78° C. was slowly added LiHMDS (1.8 mL, 1.8 mmol). The solution was stirred for 30 min, followed by addition of sat'd solution of NH4Cl (5 mL). Et2O (5 mL) was added to the ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1=CCCCC1 | C1=CCCCC1 | C1=CCCCC1.c1ccccc1 | null | CCOCC.C1CCOC1 | null | 0.5 | CC1C(O)CC=CC1S(=O)(=O)c1ccccc1>CCOCC.C1CCOC1>C[C@H]1CCC(=O)C=C1S(=O)(=O)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-59170692a13f45e899dfc7157f96b4d9 | CC(C)C1C(O)CC=CC1S(=O)(=O)c1ccccc1>>C[C@H]1CCC(=O)C=C1S(=O)(=O)c1ccccc1 | [Li+].C[Si](C)(C)[N-][Si](C)(C)C.C1(=CC=CC=C1)S(=O)(=O)C1C=CCC(C1C(C)C)O.[NH4+].[Cl-].C(C)(C)[Mg]Cl>>C1(=CC=CC=C1)S(=O)(=O)C1=CC(CC[C@@H]1C)=O | C[CH:1](C)[CH:2]1[CH:3]([OH:6])[CH2:4][CH:5]=[CH:7][CH:8]1[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>>[CH3:1][C@H:2]1[CH2:3][CH2:4][C:5](=[O:6])[CH:7]=[C:8]1[S:9](=[O:10])(=[O:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1 | CC(C)C1C(O)CC=CC1S(=O)(=O)c1ccccc1 | C[C@H]1CCC(=O)C=C1S(=O)(=O)c1ccccc1 | null | null | CCOCC.C1CCOC1 | Miscellaneous | OtherReaction | 53cf4e2066676acec66f9f3f7a3a23d51f563226cdd6f5b0777cb107a8e9d680 | ef59ba7fad669d0d82c4daf03280dc0366c9a31cf6192836b4997e72f66f9d7c | O=C1C=C(S(=O)(=O)c2ccccc2)CCC1 | C-[CH;D3;+0:1](-C)-[CH;D3;+0:2]1-[CH;D3;+0:3](-[OH;D1;+0:4])-[C:5]-[CH;D2;+0:6]=[CH;D2;+0:7]-[CH;D3;+0:8]-1-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12]>>[CH3;D1;+0:1]-[C@H;D3;+0:2]1-[CH2;D2;+0:3]-[C:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:4])-[CH;D2;+0:7]=[C;H0;D3;+0:8]-1-[#16:9](=[O;D1;H0:10])(=[O;D1;H0:11])-[c:12] | 89 | [{"value": 89.0, "product": "C1(=CC=CC=C1)S(=O)(=O)C1=CC(CC[C@@H]1C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | (1S, 55, 65)-5-Benzenesulfonyl-6-methylcyclohex-3-enol (22aMe). To a solution of epoxy-dienyl sulfone SS-9a (0.377 g, 1.6 mmol) in THF (10 mL) at −78° C. was slowly added LiHMDS (1.8 mL, 1.8 mmol). The solution was stirred for 30 min, followed by addition of sat'd solution of NH4Cl (5 mL). Et2O (5 mL) was added to the ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | C1=CCCCC1 | C1=CCCCC1 | C1=CCCCC1.c1ccccc1 | Other | CCOCC.C1CCOC1 | null | 0.5 | CC(C)C1C(O)CC=CC1S(=O)(=O)c1ccccc1>CCOCC.C1CCOC1>C[C@H]1CCC(=O)C=C1S(=O)(=O)c1ccccc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-92ca338d45f34950ac71e0f1069d5ed8 | CC(C)[C@@H]1[C@@H](S(=O)(=O)c2ccccc2)[C@@H]2O[C@@H]2C[C@@H]1O[Si](C)(C)C(C)(C)C>>C[C@@H]1[C@@H](S(=O)(=O)c2ccccc2)[C@@H]2O[C@@H]2C[C@@H]1O[Si](C)(C)C(C)(C)C | C1(=CC=CC=C1)S(=O)(=O)[C@@H]1[C@H]([C@H](C[C@H]2O[C@@H]12)O[Si](C)(C)C(C)(C)C)C(C)C>>C1(=CC=CC=C1)S(=O)(=O)[C@@H]1[C@H]([C@H](C[C@H]2O[C@@H]12)O[Si](C)(C)C(C)(C)C)C | C[CH:1](C)[C@@H:2]1[C@@H:3]([S:4](=[O:5])(=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[C@@H:13]2[O:14][C@@H:15]2[CH2:16][C@@H:17]1[O:18][Si:19]([CH3:20])([CH3:21])[C:22]([CH3:23])([CH3:24])[CH3:25]>>[CH3:1][C@@H:2]1[C@@H:3]([S:4](=[O:5])(=[O:6])[c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)[C@@H:13]2[O:14][C@@H:15]2[CH2... | CC(C)[C@@H]1[C@@H](S(=O)(=O)c2ccccc2)[C@@H]2O[C@@H]2C[C@@H]1O[Si](C)(C)C(C)(C)C | C[C@@H]1[C@@H](S(=O)(=O)c2ccccc2)[C@@H]2O[C@@H]2C[C@@H]1O[Si](C)(C)C(C)(C)C | null | null | C(Cl)(Cl)Cl | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | O=S(=O)(c1ccccc1)[C@@H]1CCC[C@H]2O[C@@H]12 | C-[CH;D3;+0:1](-C)-[C:2](-[C:3])-[C:4]>>[C:3]-[C:2](-[CH3;D1;+0:1])-[C:4] | null | [] | null | null | null | null | 1H NMR (CDCl3): δ 7.91 (m, 2H), 7.62 (m, 3H), 4.15 (ddd, J=10.4 Hz, 6.3 Hz, 4.4 Hz, 1H), 3.59 (d, J=2.4 Hz, 1H), 3.35 (d, J=3.5 Hz, 1H), 3.25 (dd, J=5.0 Hz, 4.3 Hz, 1H), 2.32 (m, 1H), 1.98 (m, 2H), 1.01 (d, J=7.2 Hz, 3H), 0.86 (s, 9H), 0.05 (s, 6H). 13C NMR (CDCl3): □138.3 134.0, 129.4, 128.4, 65.7, 65.3, 52.1, 49.4, 3... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.C1CC[C@H]2O[C@H]2C1 | Other | C(Cl)(Cl)Cl | null | null | CC(C)[C@@H]1[C@@H](S(=O)(=O)c2ccccc2)[C@@H]2O[C@@H]2C[C@@H]1O[Si](C)(C)C(C)(C)C>C(Cl)(Cl)Cl>C[C@@H]1[C@@H](S(=O)(=O)c2ccccc2)[C@@H]2O[C@@H]2C[C@@H]1O[Si](C)(C)C(C)(C)C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-78b524b9b1684a779811e8d7f54e7410 | C[C@@H]1CC=C(S(=O)(=O)c2ccccc2)[C@H](O)C1>>C[C@H]1C=CC(Sc2ccccc2)=CC[C@H]1O | [Li+].C[Si](C)(C)[N-][Si](C)(C)C.C1(=CC=CC=C1)S(=O)(=O)C=1[C@@H](C[C@@H](CC1)C)O.CCN(CC)CC.CS(=O)(=O)Cl.C1CCOC1>>C[C@@H]1[C@@H](CC=C(C=C1)SC1=CC=CC=C1)O | O=[S:6](=O)([C:5]1=[CH:13][CH2:14][C@@H:2]([CH3:1])[CH2:4][C@H:15]1[OH:16])[c:7]1[cH:8][cH:9][cH:10][cH:11][cH:12]1>>[CH3:1][C@H:2]1[CH:3]=[CH:4][C:5]([S:6][c:7]2[cH:8][cH:9][cH:10][cH:11][cH:12]2)=[CH:13][CH2:14][C@H:15]1[OH:16] | C[C@@H]1CC=C(S(=O)(=O)c2ccccc2)[C@H](O)C1 | C[C@H]1C=CC(Sc2ccccc2)=CC[C@H]1O | null | null | C1=CC=CC=C1.CC(C)O | Reduction | OtherReaction | ead1c155d9aeb0039ff40f732db8600f7696952f022e16f5b513b79008524289 | 761a2706231bc8b83597d9327ed39c5d6cf596f163d1f8c30d951ba45f12f54b | C1=CC(Sc2ccccc2)=CCCC1 | O=[S;H0;D4;+0:1](=O)(-[C;H0;D3;+0:2]1=[C:3]-[CH2;D2;+0:4]-[C@@H;D3;+0:5](-[C;D1;H3:6])-[CH2;D2;+0:7]-[C@H;D3;+0:8]-1-[O;D1;H1:9])-[c:10](:[c:11]):[c:12]>>[C;D1;H3:6]-[C@H;D3;+0:5]1-[C:13]=[CH;D2;+0:7]-[C;H0;D3;+0:2](-[S;H0;D2;+0:1]-[c:10](:[c:11]):[c:12])=[C:3]-[CH2;D2;+0:4]-[C@H;D3;+0:8]-1-[O;D1;H1:9] | 92 | [{"value": 92.0, "product": "C[C@@H]1[C@@H](CC=C(C=C1)SC1=CC=CC=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | (4S)-4-Methyl-cyclohexa-1,5-dienesulfonyl)-benzene (29z). To a solution of 24z (355 mg, 1.40 mmol) and Et3N (0.19 mL, 1.40 mmol) in THF (10 mL) at 0° C. was added 0.11 mL (1.40 m-mol) of MsCl dropwise. After stirring at 0° C. for 1 h, the reaction mixture was cooled to −78° C., and freshly prepared LiHMDS (2.8 mL, 1.0 ... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol.Sulfone | Secondary alcohol.Monosulfide | C1=CCCCC1 | C1=CCCCC=C1 | C1=CCCCC=C1.c1ccccc1 | Other | C1=CC=CC=C1.CC(C)O | 0 | 1 | C[C@@H]1CC=C(S(=O)(=O)c2ccccc2)[C@H](O)C1>C1=CC=CC=C1.CC(C)O>C[C@H]1C=CC(Sc2ccccc2)=CC[C@H]1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ddf938e6d3e84ba59942c28c81d2961f | CC(C)(C)[Si](C)(C)Cl.C[C@H]1C(S(=O)(=O)c2ccccc2)C=C(Sc2ccccc2)CC[C@H]1O[Si](C)(C)C>>C[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)C(S(=O)(=O)c2ccccc2)=C[C@H]1O | C1(=CC=CC=C1)S(=O)(=O)C1[C@@H]([C@@H](CCC(=C1)SC1=CC=CC=C1)O[Si](C)(C)C)C.CC(C)(C)[Si](C)(C)Cl.N1C=NC=C1.C1CCOC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>C1(=CC=CC=C1)S(=O)(=O)C1=C[C@H]([C@@H]([C@@H]([C@H]1C)O[Si](C)(C)C(C)(C)C)C)O | Cl[Si:5]([CH3:6])([CH3:7])[C:8]([CH3:9])([CH3:10])[CH3:11].C[Si](C)(C)[O:4][C@H:3]1[C@@H:2]([CH3:1])[CH:14]([S:15](=[O:16])(=[O:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[CH:24]=[C:25](Sc2ccccc2)[CH2:13][CH2:12]1>>[CH3:1][C@@H:2]1[C@H:3]([O:4][Si:5]([CH3:6])([CH3:7])[C:8]([CH3:9])([CH3:10])[CH3:11])[C@@H:12]([CH3... | CC(C)(C)[Si](C)(C)Cl.C[C@H]1C(S(=O)(=O)c2ccccc2)C=C(Sc2ccccc2)CC[C@H]1O[Si](C)(C)C | C[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)C(S(=O)(=O)c2ccccc2)=C[C@H]1O | null | null | CN(C)C=O | C-C Coupling | OtherReaction | 90dae55e1a53e4b0f3abc0387a901aea8b4624a7d95f6ab3ae19c8012917de80 | 81383a16bb4bb21d717e2433121f2f777f575ecc39db8d06952e063b871ee9b0 | O=S(=O)(C1=CCCCC1)c1ccccc1 | C-[Si](-C)(-C)-[O;H0;D2;+0:1]-[C:2]1-[CH2;D2;+0:3]-[CH2;D2;+0:4]-[C;H0;D3;+0:5](-S-c2:c:c:c:c:c:2)=[CH;D2;+0:6]-[CH;D3;+0:7](-[#16:8](=[O;D1;H0:9])(=[O;D1;H0:10])-[c:11])-[C@@H;D3;+0:12]-1-[C;D1;H3:13].Cl-[Si;H0;D4;+0:14](-[C;D1;H3:15])(-[C;D1;H3:16])-[C:17](-[C;D1;H3:18])(-[C;D1;H3:19])-[C;D1;H3:20]>>[C;D1;H3:18]-[C:1... | 84 | [{"value": 84.0, "product": "C1(=CC=CC=C1)S(=O)(=O)C1=C[C@H]([C@@H]([C@@H]([C@H]1C)O[Si](C)(C)C(C)(C)C)C)O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 84.0, "product": "C1(=CC=CC=C1)S(=O)(=O)C1=C[C@H]([C@@H]([C@@H]([C@H]1C)O[Si](C)(C)C(C)(C)C)C)O", "details": "CALCULATEDPERCENTYIELD", "is_desired": fal... | 70 | CELSIUS | 20 | HOUR | The mixture of diol 23 (585 mg, 2.07 mmol), TBSCl (1.0 g, 6.63 mmol), and imidazole (564 mg, 8.28 mmol) in DMF (5.0 mL) was stirred at 70° C. for 20 h under nitrogen. After being quenched by aqueous NH4Cl, the reaction mixture was extracted with diethyl ether (3×20 mL). The organic layers were washed with brine, dried ... | 10.6084/m9.figshare.5104873.v1 | null | Monosulfide.Silyl protective group.Silyl protective group | Secondary alcohol.TMS ether protective group | C1=CCCCCC1.c1ccccc1 | C1=CCCCC1 | C1=CCCCC1.c1ccccc1 | HCl | CN(C)C=O | 70 | 20 | CC(C)(C)[Si](C)(C)Cl.C[C@H]1C(S(=O)(=O)c2ccccc2)C=C(Sc2ccccc2)CC[C@H]1O[Si](C)(C)C>CN(C)C=O>C[C@@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)C(S(=O)(=O)c2ccccc2)=C[C@H]1O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-93a7b084405c4ccdb8890c3c13a68a78 | CO.Cc1ccc(C(=O)O)cc1[N+](=O)[O-]>>COC(=O)c1ccc(C)c([N+](=O)[O-])c1 | CC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].OS(=O)(=O)O.CO>>COC(C1=CC(=C(C=C1)C)[N+](=O)[O-])=O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1 | CO.Cc1ccc(C(=O)O)cc1[N+](=O)[O-] | COC(=O)c1ccc(C)c([N+](=O)[O-])c1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 98 | [{"value": 98.0, "product": "COC(C1=CC(=C(C=C1)C)[N+](=O)[O-])=O", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | null | null | A solution of 4-methyl-3-nitrobenzoic acid (27.95 g, 154 mmol) in MeOH (550 mL) was treated with concentrated H2SO4 (10 mL, 188 mmol) and heated to reflux for 17 hours. The reaction was cooled and concentrated under reduced pressure. EtOAc (300 mL) and brine (400 mL) were added and the solution cooled to 0° C. 10N NaOH... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | 0 | null | CO.Cc1ccc(C(=O)O)cc1[N+](=O)[O-]>>COC(=O)c1ccc(C)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-744fbc66c6004b2a8e9359399b847e98 | COC(=O)c1ccc(C)c([N+](=O)[O-])c1>>COC(=O)c1ccc(C)c(N)c1 | COC(C1=CC(=C(C=C1)C)[N+](=O)[O-])=O.CCOC(=O)C>>COC(C1=CC(=C(C=C1)C)N)=O | O=[N+:11]([O-])[c:10]1[c:8]([CH3:9])[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:12]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([NH2:11])[cH:12]1 | COC(=O)c1ccc(C)c([N+](=O)[O-])c1 | COC(=O)c1ccc(C)c(N)c1 | null | [Pd] | CO | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 100 | [{"value": 100.0, "product": "COC(C1=CC(=C(C=C1)C)N)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | The ester from above (29.37 g, 150 mmol) was added to a 2L Parr hydrogenation flask and dissolved in anhydrous MeOH (200 mL) plus EtOAc (25 mL). The solution was then treated with 10% Pd/C (2.25 g, 50% wet) and fitted to a hydrogenator apparatus. After purging the flask 3 times with hydrogen gas, the mixture was shaken... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | [Pd].CO | null | 1 | COC(=O)c1ccc(C)c([N+](=O)[O-])c1>[Pd].CO>COC(=O)c1ccc(C)c(N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5fcd73f86fce4816afc9ce92a1d244c5 | Cc1ncccc1C(C)C.OO>>Cc1c(C(C)C)ccc[n+]1[O-] | OO.C(C)(C)C=1C(=NC=CC1)C>>C(C)(C)C=1C(=[N+](C=CC1)[O-])C | [CH3:1][c:2]1[c:3]([CH:4]([CH3:5])[CH3:6])[cH:7][cH:8][cH:9][n:10]1.O[OH:11]>>[CH3:1][c:2]1[c:3]([CH:4]([CH3:5])[CH3:6])[cH:7][cH:8][cH:9][n+:10]1[O-:11] | Cc1ncccc1C(C)C.OO | Cc1c(C(C)C)ccc[n+]1[O-] | null | null | CC(=O)O | Functional Group Interconversion | OtherReaction | d7f3c84fb751fef5567bc0e84a2e7c0afb271257e8dfb17aa871e038ff1a84c7 | bf536f3bf8ed7b8faf08cf1c004ccd0a5e7fe59339402dd73ac837bb4a52f2ba | c1cc[nH+]cc1 | O-[OH;D1;+0:1].[C;D1;H3:2]-[c:3](:[c:4]):[n;H0;D2;+0:5]:[c:6]:[c:7]>>[C;D1;H3:2]-[c:3](:[c:4]):[n+;H0;D3:5](-[O-;H0;D1:1]):[c:6]:[c:7] | 94 | [{"value": 94.0, "product": "C(C)(C)C=1C(=[N+](C=CC1)[O-])C", "details": "PERCENTYIELD", "is_desired": false}] | 70 | CELSIUS | 18 | HOUR | A 50% solution of hydrogen peroxide (24.89 mL) was slowly added to a solution of 3-isopropyl-2-methyl-pyridine (24.5 g, 183 mmol) (Ishiguro, et al., Yakugaku Zasshi (1958) 78:220) in HOAc (280 mL). The mixture was warmed to 70° C. and stirred for 18 h, then cooled to room temperature and concentrated in vacuo to remove... | 10.6084/m9.figshare.5104873.v1 | null | Peroxide | null | c1ccncc1 | C1=CC=[NH+]C=C1 | C1=CC=[NH+]C=C1 | HO- | CC(=O)O | 70 | 18 | Cc1ncccc1C(C)C.OO>CC(=O)O>Cc1c(C(C)C)ccc[n+]1[O-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-efd252a864cb426b883c7fa6d1b0393d | Cc1c(C(C)C)ccc[n+]1[O-]>>CC(C)c1cccnc1CO | C(=O)(C(F)(F)F)OC(=O)C(F)(F)F.C(C)(C)C=1C(=[N+](C=CC1)[O-])C.C(=O)(C(F)(F)F)OC(=O)C(F)(F)F>>C(C)(C)C=1C(=NC=CC1)CO | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][n+:8]([O-:11])[c:9]1[CH3:10]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[CH2:10][OH:11] | Cc1c(C(C)C)ccc[n+]1[O-] | CC(C)c1cccnc1CO | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 7e561d7afee9600ed6bdb2a097e47ef139bafb1884a12ad7f91414ba01df7b33 | 0607ce9ac404b7f992b14bf13602ccd36eb29bd5911f2b79cc25c0bfd203a764 | c1ccncc1 | [CH3;D1;+0:1]-[c:2](:[c:3]):[n+;H0;D3:4](-[O-;H0;D1:5]):[c:6]:[c:7]>>[OH;D1;+0:5]-[CH2;D2;+0:1]-[c:2](:[c:3]):[n;H0;D2;+0:4]:[c:6]:[c:7] | 99 | [{"value": 99.0, "product": "C(C)(C)C=1C(=NC=CC1)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a stirred solution of 3-isopropyl-2-methyl-pyridine 1-oxide (26.05 g, 173 mmol) in CH2Cl2 (690 mL) was added dropwise TFAA (51.83 mL) over 30 min. under N2 then stirred for an additional 3 h. Caution: exothermic reaction on addition of TFAA. The mixture was concentrated in vacuo to a minimum volume. Brine (200 mL) w... | 10.6084/m9.figshare.5104873.v1 | null | null | Primary alcohol | C1=CC=[NH+]C=C1 | c1ccncc1 | c1ccncc1 | null | C(Cl)Cl | null | 3 | Cc1c(C(C)C)ccc[n+]1[O-]>C(Cl)Cl>CC(C)c1cccnc1CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ba0749203138458e9779665d38312ba7 | CC(C)c1cccnc1CO>>CC(C)c1cccnc1C=O | C(C)(C)C=1C(=NC=CC1)CO>>C(C)(C)C=1C(=NC=CC1)C=O | [CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[CH2:10][OH:11]>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[CH:10]=[O:11] | CC(C)c1cccnc1CO | CC(C)c1cccnc1C=O | null | O=[Mn]=O | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccncc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6] | 61.7 | [{"value": 61.0, "product": "C(C)(C)C=1C(=NC=CC1)C=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.7, "product": "C(C)(C)C=1C(=NC=CC1)C=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | To a vigorously stirred solution of (3-isopropyl-pyridin-2-yl)-methanol (26 g, 170 mmol) in CH2Cl2 (575 mL) was added MnO2 (105 g, 1.20 mol) under N2. The mixture was stirred for 18 h then filtered through a celite pad and concentrated in vacuo. Purification by column chromatography on silica gel (EtOAc/hexanes, 1:3) a... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccncc1 | null | O=[Mn]=O.C(Cl)Cl | null | 18 | CC(C)c1cccnc1CO>O=[Mn]=O.C(Cl)Cl>CC(C)c1cccnc1C=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-02b10793e76e4128a3bfb4c79c287633 | CC(C)c1cccnc1C1CC(=O)CC(c2ncccc2C(C)C)N1>>CC(C)c1cccnc1[C@@H]1CCC[C@H](c2ncccc2C(C)C)N1 | C(Cl)Cl.C(C)(C)C=1C(=NC=CC1)C1NC(CC(C1)=O)C1=NC=CC=C1C(C)C.[OH-].[K+].O.NN>>C(C)(C)C=1C(=NC=CC1)[C@@H]1N[C@@H](CCC1)C1=NC=CC=C1C(C)C | O=[C:12]1[CH2:11][CH:10]([c:9]2[c:4]([CH:2]([CH3:1])[CH3:3])[cH:5][cH:6][cH:7][n:8]2)[NH:24][CH:14]([c:15]2[n:16][cH:17][cH:18][cH:19][c:20]2[CH:21]([CH3:22])[CH3:23])[CH2:13]1>>[CH3:1][CH:2]([CH3:3])[c:4]1[cH:5][cH:6][cH:7][n:8][c:9]1[C@@H:10]1[CH2:11][CH2:12][CH2:13][C@H:14]([c:15]2[n:16][cH:17][cH:18][cH:19][c:20]2[... | CC(C)c1cccnc1C1CC(=O)CC(c2ncccc2C(C)C)N1 | CC(C)c1cccnc1[C@@H]1CCC[C@H](c2ncccc2C(C)C)N1 | null | null | C(COCCO)O | Reduction | OtherReaction | 480c86d699cecfc77c66c4f0456bd74413c6252cfa33cc10192db180010e8392 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccc([C@@H]2CCC[C@H](c3ccccn3)N2)nc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[CH2;D2;+0:1]-[C:6]-[C:5]-1 | 99 | [{"value": 99.0, "product": "C(C)(C)C=1C(=NC=CC1)[C@@H]1N[C@@H](CCC1)C1=NC=CC=C1C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.5, "product": "C(C)(C)C=1C(=NC=CC1)[C@@H]1N[C@@H](CCC1)C1=NC=CC=C1C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | null | null | To a solution of 3,3″-diisopropyl-2′,3′,5′,6′-tetrahydro-1′H-[2,2′;6′,2″]terpyridin-4′-one (106 mg, 0.314 mmol) in diethylene glycol (3 mL) were added KOH (352 mg, 6.29 mmol) and hydrazine monohydrate (0.61 mL, 12.6 mmol). The reaction mixture was heated to ˜100° C. for 1 h using a sand bath. After 1 h the temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1CCNCC1 | C1CCNCC1 | c1ccncc1.C1CCNCC1.c1ccncc1 | Other | C(COCCO)O | 100 | null | CC(C)c1cccnc1C1CC(=O)CC(c2ncccc2C(C)C)N1>C(COCCO)O>CC(C)c1cccnc1[C@@H]1CCC[C@H](c2ncccc2C(C)C)N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a94744f385074e9fbe350ec4fe05f5ea | COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=CC1=CNN(Cc2ccccc2)C1>>O=CCC1=CNN(Cc2ccccc2)C1 | Cl.[Li+].CC(C)[N-]C(C)C.C(C1=CC=CC=C1)N1NC=C(C1)C=O.C(=O)([O-])[O-].[K+].[K+].CCOCCO.C(=O)=O.[Cl-].COC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1>>C(C1=CC=CC=C1)N1NC=C(C1)CC=O | C[O:1][CH2:2][P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=[CH:3][C:4]1=[CH:5][NH:6][N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1>>[O:1]=[CH:2][CH2:3][C:4]1=[CH:5][NH:6][N:7]([CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1 | COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=CC1=CNN(Cc2ccccc2)C1 | O=CCC1=CNN(Cc2ccccc2)C1 | null | null | O.C1CCOC1 | Acylation | OtherReaction | 09b9107a36f1ae0d38aaef1be8af826b4dbd28bb89f449aa890e5f5b01b29d66 | d80bfbfdd53d8fededd98b451eddf72f4ce5a473f9fc28d89a5474331b440496 | C1=CNN(Cc2ccccc2)C1 | C-[O;H0;D2;+0:1]-[CH2;D2;+0:2]-[P+](-c1:c:c:c:c:c:1)(-c1:c:c:c:c:c:1)-c1:c:c:c:c:c:1.O=[CH;D2;+0:3]-[C:4]1=[C:5]-[#7:6]-[#7:7]-[C:8]-1>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[CH2;D2;+0:3]-[C:4]1=[C:5]-[#7:6]-[#7:7]-[C:8]-1 | 51 | [{"value": 51.0, "product": "C(C1=CC=CC=C1)N1NC=C(C1)CC=O", "details": "PERCENTYIELD", "is_desired": false}] | -15 | CELSIUS | 30 | MINUTE | To a suspension of methoxymethyl-triphenyl-phosphonium chloride (2.06 g, 6.00 mmol) in dry THF (20 mL) cooled at −15° C. (ethyl glycol/dry ice) was added LDA (2.0 M in THF, 3.1 mL, 6.2 mmol) slowly. After the addition the mixture was stirred at −15° C. for 30 min, and a solution of 2-benzyl-1H-pyrazole-4-carbaldehyde (... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ether | Aldehyde | c1ccccc1.c1ccccc1.c1ccccc1 | null | C1=CN[NH]C1.c1ccccc1 | HO- | O.C1CCOC1 | -15 | 0.5 | COC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=CC1=CNN(Cc2ccccc2)C1>O.C1CCOC1>O=CCC1=CNN(Cc2ccccc2)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3a819352c303483fb22c31446bd2567e | Cc1cccnc1[C@H]1CCC[C@@H](c2ncccc2C)N1CCC1=CNN(Cc2ccccc2)C1>>Cc1cccnc1[C@H]1CCC[C@@H](c2ncccc2C)N1CCc1cn[nH]c1 | C(C1=CC=CC=C1)N1NC=C(C1)CCN1[C@H](CCC[C@H]1C1=NC=CC=C1C)C1=NC=CC=C1C.CC(C)(C)[O-].[K+]>>CC=1C(=NC=CC1)[C@@H]1N([C@@H](CCC1)C1=NC=CC=C1C)CCC=1C=NNC1 | c1ccc(C[N:26]2[NH:25][CH:24]=[C:23]([CH2:22][CH2:21][N:20]3[C@@H:8]([c:7]4[c:2]([CH3:1])[cH:3][cH:4][cH:5][n:6]4)[CH2:9][CH2:10][CH2:11][C@H:12]3[c:13]3[n:14][cH:15][cH:16][cH:17][c:18]3[CH3:19])[CH2:27]2)cc1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[C@H:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([c:13]2[n:14][cH:15][cH:16]... | Cc1cccnc1[C@H]1CCC[C@@H](c2ncccc2C)N1CCC1=CNN(Cc2ccccc2)C1 | Cc1cccnc1[C@H]1CCC[C@@H](c2ncccc2C)N1CCc1cn[nH]c1 | null | null | CS(=O)C.C1CCOC1 | Reduction | OtherReaction | 0ef0e7d2476c164dc4ef9783c9e090afca09f3d3affdb33868b053ddda3d6ef4 | f31a913ab5bcf12fcacb773a895211f3d47e2ac9715e3c3c87407321eb648176 | c1ccc([C@H]2CCC[C@@H](c3ccccn3)N2CCc2cn[nH]c2)nc1 | [C:1]-[C:2]-[C;H0;D3;+0:3]1=[CH;D2;+0:4]-[NH;D2;+0:5]-[N;H0;D3;+0:6](-C-c2:c:c:c:c:c:2)-[CH2;D2;+0:7]-1>>[C:1]-[C:2]-[c;H0;D3;+0:3]1:[cH;D2;+0:4]:[n;H0;D2;+0:5]:[nH;D2;+0:6]:[cH;D2;+0:7]:1 | 64.4 | [{"value": 64.0, "product": "CC=1C(=NC=CC1)[C@@H]1N([C@@H](CCC1)C1=NC=CC=C1C)CCC=1C=NNC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 64.4, "product": "CC=1C(=NC=CC1)[C@@H]1N([C@@H](CCC1)C1=NC=CC=C1C)CCC=1C=NNC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 140 | CELSIUS | null | null | To a solution of (2′R,6′S)-1′-[2-(2-benzyl-1H-pyrazol-4-yl)-ethyl]-3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (0.130 g, 0.288 mmol) in dry DMSO (0.70 mL) and THF (12 mL) was added 4 Å molecular sieve (˜1 g) pre-heated at 140° C., and KOtBu (0.600 g, 5.35 mmol). The solution was bubbled with air (... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Hydrazine | null | c1ccccc1.C1=CN[NH]C1 | c1cn[nH]c1 | c1ccncc1.C1CC[NH]CC1.c1ccncc1.c1cn[nH]c1 | Other | CS(=O)C.C1CCOC1 | 140 | null | Cc1cccnc1[C@H]1CCC[C@@H](c2ncccc2C)N1CCC1=CNN(Cc2ccccc2)C1>CS(=O)C.C1CCOC1>Cc1cccnc1[C@H]1CCC[C@@H](c2ncccc2C)N1CCc1cn[nH]c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a99bbec6227e4e2e9b0c57a1c96457cd | CC(C)(Br)Br.O=C1NC(=O)c2ccccc21>>O=C1c2ccccc2C(=O)N1CCCBr | BrC(C)(C)Br.C1(C=2C(C(N1)=O)=CC=CC2)=O.[K].CN(C)C=O>>BrCCCN1C(C2=CC=CC=C2C1=O)=O | Br[C:14]([CH3:12])([CH3:13])[Br:15].[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[NH:11]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][Br:15] | CC(C)(Br)Br.O=C1NC(=O)c2ccccc21 | O=C1c2ccccc2C(=O)N1CCCBr | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f611e1a25c8eecae07db6b8e7051174b409e359915352488fcf0aa865ea115f1 | 58ee6c221c641ad7f4c021795cad4d1767fad6c977d135f8d602f3a70dc4b197 | O=C1NC(=O)c2ccccc21 | Br-[C;H0;D4;+0:1](-[Br;D1;H0:2])(-[CH3;D1;+0:3])-[CH3;D1;+0:4].[O;D1;H0:5]=[C:6]1-[NH;D2;+0:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11]-1>>[Br;D1;H0:2]-[CH2;D2;+0:1]-[CH2;D2;+0:4]-[CH2;D2;+0:3]-[N;H0;D3;+0:7]1-[C:8](=[O;D1;H0:9])-[c:10]:[c:11]-[C:6]-1=[O;D1;H0:5] | 49 | [{"value": 49.0, "product": "BrCCCN1C(C2=CC=CC=C2C1=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 17 | HOUR | To a solution of dibromopropane (0.61 mL, 6.0 mmol) in DMF (8 mL) was added potassium phthalimide (0.2756 g, 1.5 mmol), and was stirred at 90° C. for 17 hours. The mixture was concentrated, 1N NaOH (10 mL) was added, and extracted with CH2Cl2 (2×30 mL). The combined organic extracts were washed with water (1×15 mL), dr... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Unsubstituted dicarboximide | Primary halide.Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HBr | null | 90 | 17 | CC(C)(Br)Br.O=C1NC(=O)c2ccccc21>>O=C1c2ccccc2C(=O)N1CCCBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-798af5c23b554ecd94e682f9b9a291b4 | Cc1cccnc1C#N.O=C1CCC(=O)N1Br>>N#Cc1ncccc1CBr | CC(C)(C#N)N=NC(C)(C)C#N.CC=1C(=NC=CC1)C#N.BrN1C(CCC1=O)=O.CC(=O)O>>BrCC=1C(=NC=CC1)C#N | [N:1]#[C:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[CH3:9].O=C1CCC(=O)N1[Br:10]>>[N:1]#[C:2][c:3]1[n:4][cH:5][cH:6][cH:7][c:8]1[CH2:9][Br:10] | Cc1cccnc1C#N.O=C1CCC(=O)N1Br | N#Cc1ncccc1CBr | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccncc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5](-[C:6]#[N;D1;H0:7]):[#7;a:8]:[c:9]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5](-[C:6]#[N;D1;H0:7]):[#7;a:8]:[c:9] | 21.4 | [{"value": 21.0, "product": "BrCC=1C(=NC=CC1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 21.4, "product": "BrCC=1C(=NC=CC1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 3-methylpicolinonitrile (700 mg, 5.93 mmol) in CCl4 (15 mL) was added recrystallized N-bromosuccinimide (1.21 g, 6.82 mmol), followed by glacial HOAc (0.34 mL, 1.0 eq), and AIBN (97 mg, 0.60 mmol). The resultant mixture was heated to 65° C. for 3 hours, 80° C. for 2 hours, and then cooled to room tempe... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccncc1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | Cc1cccnc1C#N.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>N#Cc1ncccc1CBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-eda5f317d500415fb4a65748bc302b1f | Cc1cccnc1[C@@H]1CCC[C@H](c2ncccc2C)N1.N#Cc1cscc1CBr>>Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1cscc1C#N | CC=1C(=NC=CC1)[C@@H]1N[C@@H](CCC1)C1=NC=CC=C1C.BrCC=1C(=CSC1)C#N.CCN(C(C)C)C(C)C>>CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC=1C(=CSC1)C#N | [CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[C@@H:8]1[CH2:9][CH2:10][CH2:11][C@H:12]([c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[CH3:19])[NH:20]1.Br[CH2:21][c:22]1[cH:23][s:24][cH:25][c:26]1[C:27]#[N:28]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH:15][cH:16][cH:17][c:18... | Cc1cccnc1[C@@H]1CCC[C@H](c2ncccc2C)N1.N#Cc1cscc1CBr | Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1cscc1C#N | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(C2CCCC(c3ccccn3)N2Cc2ccsc2)nc1 | Br-[CH2;D2;+0:1]-[c:2]1:[c:3]:[#16;a:4]:[c:5]:[c:6]:1.[c:7]:[#7;a:8]:[c:9](-[C@@H;D3;+0:10]1-[C:11]-[C:12]-[C:13]-[C@H;D3;+0:14](-[c:15](:[c:16]):[#7;a:17]:[c:18])-[NH;D2;+0:19]-1):[c:20]>>[c:7]:[#7;a:8]:[c:9](-[CH;D3;+0:10]1-[C:11]-[C:12]-[C:13]-[CH;D3;+0:14](-[c:15](:[c:16]):[#7;a:17]:[c:18])-[N;H0;D3;+0:19]-1-[CH2;D... | 84 | [{"value": 84.0, "product": "CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC=1C(=CSC1)C#N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.1, "product": "CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC=1C(=CSC1)C#N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure A: A solution of 3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-cis-[2,2′;6′,2″]terpyridine (0.097 g, 0.37 mmol), 4-bromomethyl-thiophene-3-carbonitrile (0.168 g, 0.83 mmol) (Terpstra, J. W., et al., J. Org. Chem. (1986) 51:230-238), KI (21 mg, 0.13 mmol), and DIPEA (0.15 mL, 0.86 mmol) in DMF (3 mL)... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccncc1.C1CC[NH]CC1.c1ccncc1.c1ccsc1 | HBr | CN(C)C=O | null | null | Cc1cccnc1[C@@H]1CCC[C@H](c2ncccc2C)N1.N#Cc1cscc1CBr>CN(C)C=O>Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1cscc1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-53ada5f6a5134fde91e72f7c8481bc5d | CS(=O)(=O)Cl.OCCc1cncs1>>CS(=O)(=O)OCCc1cncs1 | O.S1C=NC=C1CCO.CS(=O)(=O)Cl.CCN(CC)CC>>S1C=NC=C1CCOS(=O)(=O)C | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][CH2:7][c:8]1[cH:9][n:10][cH:11][s:12]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][CH2:7][c:8]1[cH:9][n:10][cH:11][s:12]1 | CS(=O)(=O)Cl.OCCc1cncs1 | CS(=O)(=O)OCCc1cncs1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | c1cscn1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4] | 100 | [{"value": 100.0, "product": "S1C=NC=C1CCOS(=O)(=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "S1C=NC=C1CCOS(=O)(=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | At 0° C., to a solution of 2-thiazol-5-yl-ethanol (0.154 g, 1.19 mmol) in CH2Cl2 (10 mL) was added MsCl (0.150 g, 1.31 mmol) and Et3N (0.180 g, 1.79 mmol). The mixture was stirred at room temperature for 1 h. Water (20 mL) was added, and the mixture was extracted with CH2Cl2 (3×30 mL). The extracts were combined and dr... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1cscn1 | HCl | C(Cl)Cl | null | 1 | CS(=O)(=O)Cl.OCCc1cncs1>C(Cl)Cl>CS(=O)(=O)OCCc1cncs1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e49c06edb6844f65a15f673b085d9f81 | CS(=O)(=O)Cl.O=[N+]([O-])c1ccccc1S(=O)(=O)N(Cc1ccc(CO)cc1)Cc1ccccn1>>CS(=O)(=O)OCc1ccc(CN(Cc2ccccn2)S(=O)(=O)c2ccccc2[N+](=O)[O-])cc1 | C(=O)(O)[O-].[Na+].OCC1=CC=C(CN(S(=O)(=O)C2=C(C=CC=C2)[N+](=O)[O-])CC2=NC=CC=C2)C=C1.CCN(CC)CC.CS(=O)(=O)Cl.CCN(CC)CC.CS(=O)(=O)Cl>>[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)N(CC1=NC=CC=C1)CC1=CC=C(COS(=O)(=O)C)C=C1 | Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][N:12]([CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][n:19]2)[S:20](=[O:21])(=[O:22])[c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]2[N+:29](=[O:30])[O-:31])[cH:32][cH:33]1>>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][c:7]1[cH:8][cH:9][c:10]([CH2:11][N:12... | CS(=O)(=O)Cl.O=[N+]([O-])c1ccccc1S(=O)(=O)N(Cc1ccc(CO)cc1)Cc1ccccn1 | CS(=O)(=O)OCc1ccc(CN(Cc2ccccn2)S(=O)(=O)c2ccccc2[N+](=O)[O-])cc1 | null | null | C(Cl)Cl | Acylation | Formation of Sulfonic Esters | 2fa969eb2c954bb96793348a1b2335ec63fbd290dadec6e3e02295e1768e64cf | cb77b899e4adf980b1def97230ef2861660fd7f9602260ec64747d9afd3a795a | O=S(=O)(c1ccccc1)N(Cc1ccccc1)Cc1ccccn1 | Cl-[S;H0;D4;+0:1](-[C;D1;H3:2])(=[O;D1;H0:3])=[O;D1;H0:4].[OH;D1;+0:5]-[C:6]-[c:7]>>[C;D1;H3:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-[C:6]-[c:7] | 95 | [{"value": 95.0, "product": "[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)N(CC1=NC=CC=C1)CC1=CC=C(COS(=O)(=O)C)C=C1", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 2 | HOUR | To a stirring solution of N-(4-hydroxymethyl-benzyl)-2-nitro-N-pyridin-2-ylmethyl-benzenesulfonamide (Bridger, et al., U.S. Ser. No. 09/111,895) (0.2096 g, 0.51 mmol) in CH2Cl2 (5 mL) at 0° C. under Ar, was added Et3N (0.14 mL, 1.02 mmol) and MsCl (0.05 mL, 0.66 mmol). The mixture was stirred at 0° C. for 2 hours, then... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Sulfonyl halide | Mesylate | null | null | c1ccccc1.c1ccncc1.c1ccccc1 | HCl | C(Cl)Cl | 0 | 2 | CS(=O)(=O)Cl.O=[N+]([O-])c1ccccc1S(=O)(=O)N(Cc1ccc(CO)cc1)Cc1ccccn1>C(Cl)Cl>CS(=O)(=O)OCc1ccc(CN(Cc2ccccn2)S(=O)(=O)c2ccccc2[N+](=O)[O-])cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-384691ba1af0445eb367e3e072844f60 | Cc1cnc(CO)c(C)c1>>Cc1cnc(C=O)c(C)c1 | CC=1C(=NC=C(C1)C)CO>>CC=1C(=NC=C(C1)C)C=O | [CH3:1][c:2]1[cH:3][n:4][c:5]([CH2:6][OH:7])[c:8]([CH3:9])[cH:10]1>>[CH3:1][c:2]1[cH:3][n:4][c:5]([CH:6]=[O:7])[c:8]([CH3:9])[cH:10]1 | Cc1cnc(CO)c(C)c1 | Cc1cnc(C=O)c(C)c1 | null | O=[Mn]=O | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccncc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | null | null | null | null | To a solution of (3,5-dimethyl-pyridin-2-yl)-methanol (2.12 g, 15.45 mmol) (Weidmann, K., et al., J. Med. Chem. (1992) 35:438-450) in CH2Cl2 (50 mL) was added MnO2 (9.41 g, 108.18 mmol) and the reaction mixture was refluxed overnight. Then it was cooled and the mixture was filtered through a layer of celite. The filtra... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccncc1 | null | O=[Mn]=O.C(Cl)Cl | null | null | Cc1cnc(CO)c(C)c1>O=[Mn]=O.C(Cl)Cl>Cc1cnc(C=O)c(C)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-3f169f4154fd4ae78f611376589451ea | Cc1cccnc1C1CC(C)(O)CC(c2ncccc2C)N1.O=C1c2ccccc2C(=O)N1CCCCBr>>Cc1cccnc1C1CC(C)(O)CC(c2ncccc2C)N1CCCCN1C(=O)c2ccccc2C1=O | CC=1C(=NC=CC1)C1NC(CC(C1)(O)C)C1=NC=CC=C1C.BrCCCCN1C(C2=CC=CC=C2C1=O)=O.CCN(C(C)C)C(C)C>>OC1(CC(N(C(C1)C1=NC=CC=C1C)CCCCN1C(C2=CC=CC=C2C1=O)=O)C1=NC=CC=C1C)C | [CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][C:10]([CH3:11])([OH:12])[CH2:13][CH:14]([c:15]2[n:16][cH:17][cH:18][cH:19][c:20]2[CH3:21])[NH:22]1.Br[CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[C:28](=[O:29])[c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]2[C:36]1=[O:37]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[... | Cc1cccnc1C1CC(C)(O)CC(c2ncccc2C)N1.O=C1c2ccccc2C(=O)N1CCCCBr | Cc1cccnc1C1CC(C)(O)CC(c2ncccc2C)N1CCCCN1C(=O)c2ccccc2C1=O | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | O=C1c2ccccc2C(=O)N1CCCCN1C(c2ccccn2)CCCC1c1ccccn1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]:[c:5]-[C:6](-[C:7])-[NH;D2;+0:8]-[C:9](-[c:10]:[#7;a:11])-[C:12]>>[#7;a:4]:[c:5]-[C:6](-[C:7])-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:9](-[c:10]:[#7;a:11])-[C:12] | null | [] | 60 | CELSIUS | 24 | HOUR | To a solution of meso-2′β,6′β-[3,4′,3″-trimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridin-4′-ol (0.2499 g, 0.84 mmol) in DMF (9 mL) was added 2-(4-bromo-butyl)-isoindole-1,3-dione (0.2605 g, 0.92 mmol), KI (0.0142 g, 0.08 mmol), and DIPEA (0.29 mL, 1.68 mmol), and stirred at 60° C. for 24 hours. The mixture w... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccncc1.C1CC[NH]CC1.c1ccncc1.c1ccc2c(c1)C[NH]C2 | HBr | CN(C)C=O | 60 | 24 | Cc1cccnc1C1CC(C)(O)CC(c2ncccc2C)N1.O=C1c2ccccc2C(=O)N1CCCCBr>CN(C)C=O>Cc1cccnc1C1CC(C)(O)CC(c2ncccc2C)N1CCCCN1C(=O)c2ccccc2C1=O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-551da803035448cea5dce0c49a883354 | COC(=O)c1cc(C#N)ccc1CBr.Cc1cccnc1C1CCCC(c2ncccc2C)N1>>COC(=O)c1cc(C#N)ccc1CN1C(c2ncccc2C)CCCC1c1ncccc1C | CC=1C(=NC=CC1)C1NC(CCC1)C1=NC=CC=C1C.COC(C1=C(C=CC(=C1)C#N)CBr)=O>>COC(C1=C(C=CC(=C1)C#N)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C)=O | Br[CH2:13][c:12]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][c:7]([C:8]#[N:9])[cH:10][cH:11]1.[NH:14]1[CH:15]([c:16]2[n:17][cH:18][cH:19][cH:20][c:21]2[CH3:22])[CH2:23][CH2:24][CH2:25][CH:26]1[c:27]1[n:28][cH:29][cH:30][cH:31][c:32]1[CH3:33]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([C:8]#[N:9])[cH:10][cH:11][c:12]1[CH2:1... | COC(=O)c1cc(C#N)ccc1CBr.Cc1cccnc1C1CCCC(c2ncccc2C)N1 | COC(=O)c1cc(C#N)ccc1CN1C(c2ncccc2C)CCCC1c1ncccc1C | null | null | null | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2C(c3ccccn3)CCCC2c2ccccn2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].[#7;a:8]:[c:9]-[C:10](-[C:11])-[NH;D2;+0:12]-[C:13](-[c:14]:[#7;a:15])-[C:16]>>[#7;a:8]:[c:9]-[C:10](-[C:11])-[N;H0;D3;+0:12](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7])-[C:13](-[c:14]:[#7;a:15])-[C:16] | 78 | [{"value": 78.0, "product": "COC(C1=C(C=CC(=C1)C#N)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.6, "product": "COC(C1=C(C=CC(=C1)C#N)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Following General Procedure A: 3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (1.6 g, 6.0 mmol) was reacted with 2-bromomethyl-5-cyano-benzoic acid methyl ester (1.5 g, 6.0 mmol) to give 5-cyano-2-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-benzoic acid methyl ester ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HBr | null | null | null | COC(=O)c1cc(C#N)ccc1CBr.Cc1cccnc1C1CCCC(c2ncccc2C)N1>>COC(=O)c1cc(C#N)ccc1CN1C(c2ncccc2C)CCCC1c1ncccc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a9159759d5ba40b1905a655940fbe6f2 | COC(=O)c1cc(C#N)ccc1CN1C(c2ncccc2C)CCCC1c1ncccc1C>>Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccc(C#N)cc1CO | COC(C1=C(C=CC(=C1)C#N)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C)=O.[Li+].[BH4-]>>CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC1=C(C=C(C#N)C=C1)CO | CO[C:30]([c:29]1[c:22]([CH2:21][N:20]2[CH:8]([c:7]3[c:2]([CH3:1])[cH:3][cH:4][cH:5][n:6]3)[CH2:9][CH2:10][CH2:11][CH:12]2[c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[CH3:19])[cH:23][cH:24][c:25]([C:26]#[N:27])[cH:28]1)=[O:31]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH... | COC(=O)c1cc(C#N)ccc1CN1C(c2ncccc2C)CCCC1c1ncccc1C | Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccc(C#N)cc1CO | null | null | CO | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(CN2C(c3ccccn3)CCCC2c2ccccn2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 86 | [{"value": 86.0, "product": "CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC1=C(C=C(C#N)C=C1)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | To a stirred, room temperature solution of the ester from above (2.05 g, 4.6 mmol) in MeOH (50 mL) was added LiBH4 (1.0 g, 50 mmol) in three portions. Effervescence was observed, and the mixture was stirred for 3.5 hours. The mixture was concentrated and 1 N NaOH (50 mL) was added to the resultant residue. The aqueous ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccncc1.C1CC[NH]CC1.c1ccncc1.c1ccccc1 | Other | CO | null | 3.5 | COC(=O)c1cc(C#N)ccc1CN1C(c2ncccc2C)CCCC1c1ncccc1C>CO>Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccc(C#N)cc1CO |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1e472432ad8f4a5b837c819eb7a792f7 | Cc1ccc(Br)c(F)c1>>Cc1ccc(C#N)c(F)c1 | BrC1=C(C=C(C=C1)C)F.CN(C)C=O>>FC1=C(C#N)C=CC(=C1)C | Br[c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:10][c:8]1[F:9]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6]#[N:7])[c:8]([F:9])[cH:10]1 | Cc1ccc(Br)c(F)c1 | Cc1ccc(C#N)c(F)c1 | null | [C-]#N.[C-]#N.[Zn+2].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | null | Miscellaneous | OtherReaction | 3ae4da8b7f110de99cf8afc091b6f0c8540050148e425770f8030bce1480042c | 73a96fe5e833259ca394a42f82d6cc2ee7231bcde92d95030d2893b90c3fef76 | c1ccccc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[F;D1;H0:5]):[c:6]>>[F;D1;H0:5]-[c:4](:[c:6]):[c;H0;D3;+0:1](-[C:7]#[N;D1;H0:8]):[c:2]:[c:3] | 65 | [{"value": 65.0, "product": "FC1=C(C#N)C=CC(=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | 130 | CELSIUS | null | null | Under N2, to a suspension of 1-bromo-2-fluoro-4-methyl-benzene (2.59 g, 13.7 mmol) and Zn(CN)2 (1.60 g, 13.7 mmol) in dry DMF (50 mL) was added 1,1′-bis(diphenylphosphino)ferrocene (DPPF) (0.0753 g, 0.136 mmol) and Pd2(dba)3 (dba=di(benzylidene)acetone) (0.0623 g, 0.0681 mmol). After the mixture was heated at 130° C. f... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | Br- | [C-]#N.[C-]#N.[Zn+2].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd] | 130 | null | Cc1ccc(Br)c(F)c1>[C-]#N.[C-]#N.[Zn+2].C1(=CC=CC=C1)P([C-]1C=CC=C1)C1=CC=CC=C1.[C-]1(C=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Fe+2].C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.C=1C=CC(=CC1)/C=C/C(=O)/C=C/C2=CC=CC=C2.[Pd].[Pd]>Cc1ccc(C#N)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9895fd7b8454479c8a6517c73ce07583 | Cc1ccc(C#N)c(F)c1.O=C1CCC(=O)N1Br>>N#Cc1ccc(CBr)cc1F | [O-]S(=O)(=S)[O-].[Na+].[Na+].FC1=C(C#N)C=CC(=C1)C.N(=NC1(CCCCC1)C#N)C1(CCCCC1)C#N.C1CC(=O)N(C1=O)Br>>BrCC1=CC(=C(C#N)C=C1)F | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH3:7])[cH:9][c:10]1[F:11].O=C1CCC(=O)N1[Br:8]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][Br:8])[cH:9][c:10]1[F:11] | Cc1ccc(C#N)c(F)c1.O=C1CCC(=O)N1Br | N#Cc1ccc(CBr)cc1F | null | null | O.C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 65.1 | [{"value": 65.0, "product": "BrCC1=CC(=C(C#N)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 65.1, "product": "BrCC1=CC(=C(C#N)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-fluoro-4-methyl-benzonitrile (1.45 g, 10.7 mmol) in CCl4 (100 mL) was added 1,1′-azobis(cyclohexanecarbonitrile) (0.240 g, 0.982 mmol) and NBS (2.19 g, 12.3 mmol). The mixture was stirred and heated at reflux overnight, and then cooled to room temperature. A solution of Na2S2O3 (5 g) in H2O (100 mL) ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | O.C(Cl)(Cl)(Cl)Cl | null | null | Cc1ccc(C#N)c(F)c1.O=C1CCC(=O)N1Br>O.C(Cl)(Cl)(Cl)Cl>N#Cc1ccc(CBr)cc1F |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b7b50d1e207e4d1fad21507dc139f2b0 | Cc1cccnc1[C@@H]1CCC[C@H](c2ncccc2C)N1.N#Cc1ccc(CBr)cc1F>>Cc1cccnc1[C@H]1CCC[C@@H](c2ncccc2C)N1Cc1ccc(C#N)c(F)c1 | CC=1C(=NC=CC1)[C@@H]1N[C@@H](CCC1)C1=NC=CC=C1C.BrCC1=CC(=C(C#N)C=C1)F.CCN(C(C)C)C(C)C>>CC=1C(=NC=CC1)[C@@H]1N([C@@H](CCC1)C1=NC=CC=C1C)CC1=CC(=C(C#N)C=C1)F | [CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[C@@H:8]1[CH2:9][CH2:10][CH2:11][C@H:12]([c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[CH3:19])[NH:20]1.Br[CH2:21][c:22]1[cH:23][cH:24][c:25]([C:26]#[N:27])[c:28]([F:29])[cH:30]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[C@H:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([c:13]2[n:14][cH:15... | Cc1cccnc1[C@@H]1CCC[C@H](c2ncccc2C)N1.N#Cc1ccc(CBr)cc1F | Cc1cccnc1[C@H]1CCC[C@@H](c2ncccc2C)N1Cc1ccc(C#N)c(F)c1 | null | null | CC#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2[C@@H](c3ccccn3)CCC[C@H]2c2ccccn2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]:[c:6]-[C:7](-[C:8])-[NH;D2;+0:9]-[C:10](-[c:11]:[#7;a:12])-[C:13]>>[#7;a:5]:[c:6]-[C:7](-[C:8])-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10](-[c:11]:[#7;a:12])-[C:13] | 100 | [{"value": 100.0, "product": "CC=1C(=NC=CC1)[C@@H]1N([C@@H](CCC1)C1=NC=CC=C1C)CC1=CC(=C(C#N)C=C1)F", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.9, "product": "CC=1C(=NC=CC1)[C@@H]1N([C@@H](CCC1)C1=NC=CC=C1C)CC1=CC(=C(C#N)C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 16 | HOUR | A mixture of (2′R,6′S)-3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (0.267 g, 1.00 mmol), 4-bromomethyl-2-fluoro-benzonitrile (0.321 g, 0.1.50 mmol), DIPEA (0.259 g, 2.00 mmol) and KI (0.017 g, 0.10 mmol) in dry CH3CN (10 mL) was stirred at 60° C. for 16 h. After that period of time the CH3CN was r... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccncc1.C1CC[NH]CC1.c1ccncc1.c1ccccc1 | HBr | CC#N | 60 | 16 | Cc1cccnc1[C@@H]1CCC[C@H](c2ncccc2C)N1.N#Cc1ccc(CBr)cc1F>CC#N>Cc1cccnc1[C@H]1CCC[C@@H](c2ncccc2C)N1Cc1ccc(C#N)c(F)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-41ffeaac47594f33aa948715cc781f89 | CC(C)=NO.Cc1cccnc1[C@H]1CCC[C@@H](c2ncccc2C)N1Cc1ccc(C#N)c(F)c1>>CC(C)=NOc1cc(CN2[C@@H](c3ncccc3C)CCC[C@H]2c2ncccc2C)ccc1C#N | CC=1C(=NC=CC1)[C@@H]1N([C@@H](CCC1)C1=NC=CC=C1C)CC1=CC(=C(C#N)C=C1)F.CC(C)([O-])C.[K+].CC(C)=NO>>CC=1C(=NC=CC1)[C@@H]1N([C@@H](CCC1)C1=NC=CC=C1C)CC1=CC(=C(C#N)C=C1)ON=C(C)C | [CH3:1][C:2]([CH3:3])=[N:4][OH:5].F[c:6]1[cH:7][c:8]([CH2:9][N:10]2[C@@H:11]([c:12]3[n:13][cH:14][cH:15][cH:16][c:17]3[CH3:18])[CH2:19][CH2:20][CH2:21][C@H:22]2[c:23]2[n:24][cH:25][cH:26][cH:27][c:28]2[CH3:29])[cH:30][cH:31][c:32]1[C:33]#[N:34]>>[CH3:1][C:2]([CH3:3])=[N:4][O:5][c:6]1[cH:7][c:8]([CH2:9][N:10]2[C@@H:11](... | CC(C)=NO.Cc1cccnc1[C@H]1CCC[C@@H](c2ncccc2C)N1Cc1ccc(C#N)c(F)c1 | CC(C)=NOc1cc(CN2[C@@H](c3ncccc3C)CCC[C@H]2c2ncccc2C)ccc1C#N | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 4074777e8d881b991351d02d1bc762626b9bc33d60e315f16350fd17e7674c5e | 16e2061367461bda1ff490f3d967aaccaa7d481e8df8d02752e2a63e0ea13301 | c1ccc(CN2[C@@H](c3ccccn3)CCC[C@H]2c2ccccn2)cc1 | F-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7].[C;D1;H3:8]-[C:9](-[C;D1;H3:10])=[#7:11]-[OH;D1;+0:12]>>[C;D1;H3:8]-[C:9](-[C;D1;H3:10])=[#7:11]-[O;H0;D2;+0:12]-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4](-[C:5]#[N;D1;H0:6]):[c:7] | 69 | [{"value": 69.0, "product": "CC=1C(=NC=CC1)[C@@H]1N([C@@H](CCC1)C1=NC=CC=C1C)CC1=CC(=C(C#N)C=C1)ON=C(C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 68.6, "product": "CC=1C(=NC=CC1)[C@@H]1N([C@@H](CCC1)C1=NC=CC=C1C)CC1=CC(=C(C#N)C=C1)ON=C(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 30 | MINUTE | To a solution of potassium tert-butoxide (0.140 g, 1.25 mmol) in dry DMF (5 mL) was added acetone oxime (0.0877 g, 1.20 mmol), and the mixture was stirred for 30 min. A solution of 4-((2′R,6′S)-3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-2-fluoro-benzonitrile (0.400 g, 1.00 mmol) in dry... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Oxime | null | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HF | CN(C)C=O | null | 0.5 | CC(C)=NO.Cc1cccnc1[C@H]1CCC[C@@H](c2ncccc2C)N1Cc1ccc(C#N)c(F)c1>CN(C)C=O>CC(C)=NOc1cc(CN2[C@@H](c3ncccc3C)CCC[C@H]2c2ncccc2C)ccc1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-64e1b511083d4b89a70af233551c73c8 | CC(C)=NOc1cc(CN2[C@@H](c3ncccc3C)CCC[C@H]2c2ncccc2C)ccc1C#N>>Cc1cccnc1[C@H]1CCC[C@@H](c2ncccc2C)N1Cc1ccc2c(N)noc2c1 | CC=1C(=NC=CC1)[C@@H]1N([C@@H](CCC1)C1=NC=CC=C1C)CC1=CC(=C(C#N)C=C1)ON=C(C)C.Cl>>CC=1C(=NC=CC1)[C@H]1N([C@H](CCC1)C1=NC=CC=C1C)CC1=CC2=C(C(=NO2)N)C=C1 | CC(C)=[N:28][O:29][c:30]1[c:25]([C:26]#[N:27])[cH:24][cH:23][c:22]([CH2:21][N:20]2[C@H:8]([c:7]3[c:2]([CH3:1])[cH:3][cH:4][cH:5][n:6]3)[CH2:9][CH2:10][CH2:11][C@@H:12]2[c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[CH3:19])[cH:31]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[C@H:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([c:13]2[n... | CC(C)=NOc1cc(CN2[C@@H](c3ncccc3C)CCC[C@H]2c2ncccc2C)ccc1C#N | Cc1cccnc1[C@H]1CCC[C@@H](c2ncccc2C)N1Cc1ccc2c(N)noc2c1 | null | null | CCO | Aromatic Heterocycle Formation | OtherReaction | b0c8b6cab702ae896823dfc39bf3c91df5af1f06a524f3e4589ddf87232b1bc2 | f7bbda299ac8fe6ebc980c7e96a23faca5969207a0ba4ec41cb02caa3616b51d | c1ccc([C@H]2CCC[C@@H](c3ccccn3)N2Cc2ccc3cnoc3c2)nc1 | C-C(-C)=[N;H0;D2;+0:1]-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5](-[C;H0;D2;+0:6]#[N;H0;D1;+0:7]):[c:8]>>[NH2;D1;+0:7]-[c;H0;D3;+0:6]1:[n;H0;D2;+0:1]:[o;H0;D2;+0:2]:[c:3](:[c:4]):[c:5]:1:[c:8] | 62 | [{"value": 62.0, "product": "CC=1C(=NC=CC1)[C@H]1N([C@H](CCC1)C1=NC=CC=C1C)CC1=CC2=C(C(=NO2)N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 62.0, "product": "CC=1C(=NC=CC1)[C@H]1N([C@H](CCC1)C1=NC=CC=C1C)CC1=CC2=C(C(=NO2)N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-((2′R,6′S)-3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-2-isopropylideneaminooxy-benzonitrile (0.145 g, 0.320 mmol) in EtOH (4 mL) was added aqueous HCl (3 N, 4 mL), and the mixture was stirred and heated at reflux overnight. The mixture was then cooled to room tempera... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | c1ccccc1 | c1ccc2oncc2c1 | c1ccncc1.C1CC[NH]CC1.c1ccncc1.c1ccc2oncc2c1 | Other | CCO | null | null | CC(C)=NOc1cc(CN2[C@@H](c3ncccc3C)CCC[C@H]2c2ncccc2C)ccc1C#N>CCO>Cc1cccnc1[C@H]1CCC[C@@H](c2ncccc2C)N1Cc1ccc2c(N)noc2c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e89c238f80f842dc9a596346db785b73 | COC(=O)c1cc(C#N)ccc1C.O=S(=O)(O)O>>Cc1ccc(C(=O)O)cc1C(=O)O | COC(C1=C(C=CC(=C1)C#N)C)=O.S(O)(O)(=O)=O.O>>CC1=C(C=C(C(=O)O)C=C1)C(=O)O | C[O:13][C:11]([c:10]1[c:2]([CH3:1])[cH:3][cH:4][c:5]([C:6]#N)[cH:9]1)=[O:12].O=S(=O)([OH:7])[OH:8]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([C:6](=[O:7])[OH:8])[cH:9][c:10]1[C:11](=[O:12])[OH:13] | COC(=O)c1cc(C#N)ccc1C.O=S(=O)(O)O | Cc1ccc(C(=O)O)cc1C(=O)O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 04f6f47359a38696a2f676a2c8a4c8f2bdd2e4c4c96cb5a4094b7353433a7559 | a005c00caf42b66f67212cff26e6319025c9c1a53adbd7d3253c8ef6782e7b51 | c1ccccc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]:[c:5]:[c:6](-[C;H0;D2;+0:7]#N):[c:8].O=S(=O)(-[OH;D1;+0:9])-[OH;D1;+0:10]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]:[c:5]:[c:6](-[C;H0;D3;+0:7](=[O;H0;D1;+0:9])-[OH;D1;+0:10]):[c:8] | null | [] | 150 | CELSIUS | 4 | HOUR | 5-Cyano-2-methyl-benzoic acid methyl ester (1.09 g, 6.22 mmol) was suspended in a mixture of water (25 mL) and concentrated sulfuric acid (10 mL). The yellow solution was stirred at 150° C. for 4 hours to give a pale yellow slurry. The reaction mixture was cooled to room temperature and the precipitate was isolated via... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitrile | Carboxylic acid.Carboxylic acid | null | null | c1ccccc1 | HO- | null | 150 | 4 | COC(=O)c1cc(C#N)ccc1C.O=S(=O)(O)O>>Cc1ccc(C(=O)O)cc1C(=O)O |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-da4dcd5cf6f748469c422da922640649 | COC(=O)c1ccc(C)c(C(=O)OC)c1.O=C1CCC(=O)N1Br>>COC(=O)c1ccc(CBr)c(C(=O)OC)c1 | N(=NC1(CCCCC1)C#N)C1(CCCCC1)C#N.COC(C1=CC(C(=O)OC)=C(C=C1)C)=O.BrN1C(CCC1=O)=O>>COC(C1=CC(C(=O)OC)=C(C=C1)CBr)=O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:11]([C:12](=[O:13])[O:14][CH3:15])[cH:16]1.O=C1CCC(=O)N1[Br:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][Br:10])[c:11]([C:12](=[O:13])[O:14][CH3:15])[cH:16]1 | COC(=O)c1ccc(C)c(C(=O)OC)c1.O=C1CCC(=O)N1Br | COC(=O)c1ccc(CBr)c(C(=O)OC)c1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[CH3;D1;+0:7]):[c:8]>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[CH2;D2;+0:7]-[Br;H0;D1;+0:1]):[c:8] | 72 | [{"value": 72.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 4-Methyl-isophthalic acid dimethyl ester (1.06 g, 5.10 mmol), N-bromosuccinimide (1.00 g, 5.61 mmol) and 1,1′-azobis(cyclohexanecarbonitrile) (0.31 g, 1.27 mmol) were suspended in carbon tetrachloride (22 mL) and the resulting mixture was refluxed for 16 hours under N2. The orange solution was concentrated under reduce... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | COC(=O)c1ccc(C)c(C(=O)OC)c1.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>COC(=O)c1ccc(CBr)c(C(=O)OC)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-cd83c06abdbc466b91d443a6d698ad5a | COC(=O)c1cc(C#N)ccc1CBr.Cc1cccnc1C1CCCC(c2ncccc2C)N1>>COC(=O)c1cc(C#N)ccc1CN1C(c2ncccc2C)CCCC1c1ncccc1C | CC=1C(=NC=CC1)C1NC(CCC1)C1=NC=CC=C1C.COC(C1=C(C=CC(=C1)C#N)CBr)=O.CCN(C(C)C)C(C)C>>COC(C1=C(C=CC(=C1)C#N)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C)=O | Br[CH2:13][c:12]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][c:7]([C:8]#[N:9])[cH:10][cH:11]1.[NH:14]1[CH:15]([c:16]2[n:17][cH:18][cH:19][cH:20][c:21]2[CH3:22])[CH2:23][CH2:24][CH2:25][CH:26]1[c:27]1[n:28][cH:29][cH:30][cH:31][c:32]1[CH3:33]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([C:8]#[N:9])[cH:10][cH:11][c:12]1[CH2:1... | COC(=O)c1cc(C#N)ccc1CBr.Cc1cccnc1C1CCCC(c2ncccc2C)N1 | COC(=O)c1cc(C#N)ccc1CN1C(c2ncccc2C)CCCC1c1ncccc1C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2C(c3ccccn3)CCCC2c2ccccn2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].[#7;a:8]:[c:9]-[C:10](-[C:11])-[NH;D2;+0:12]-[C:13](-[c:14]:[#7;a:15])-[C:16]>>[#7;a:8]:[c:9]-[C:10](-[C:11])-[N;H0;D3;+0:12](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7])-[C:13](-[c:14]:[#7;a:15])-[C:16] | 96.1 | [{"value": 96.0, "product": "COC(C1=C(C=CC(=C1)C#N)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.1, "product": "COC(C1=C(C=CC(=C1)C#N)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure A: A solution of 3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (0.260 g, 0.98 mmol), 2-bromomethyl-5-cyano-benzoic acid methyl ester (0.360 g, 1.42 mmol), KI (37 mg, 0.22 mmol), and DIPEA (0.35 mL, 2.01 mmol) in DMF (5 mL) was heated at 60° C. for 17 hours. Purification of th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HBr | CN(C)C=O | null | null | COC(=O)c1cc(C#N)ccc1CBr.Cc1cccnc1C1CCCC(c2ncccc2C)N1>CN(C)C=O>COC(=O)c1cc(C#N)ccc1CN1C(c2ncccc2C)CCCC1c1ncccc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-72f2007f948d4e52b9d8b0a1553167a4 | Cc1cccnc1C1CCCC(c2ncccc2C)N1.N#Cc1ccccc1CBr>>Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccccc1C#N | CC=1C(=NC=CC1)C1NC(CCC1)C1=NC=CC=C1C.BrCC=1C(=CC=CC1)C#N.CCN(C(C)C)C(C)C>>CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC1=C(C#N)C=CC=C1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[CH3:19])[NH:20]1.Br[CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][c:27]1[C:28]#[N:29]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH:15][cH:16][cH:17]... | Cc1cccnc1C1CCCC(c2ncccc2C)N1.N#Cc1ccccc1CBr | Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccccc1C#N | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2C(c3ccccn3)CCCC2c2ccccn2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]:[c:6]-[C:7](-[C:8])-[NH;D2;+0:9]-[C:10](-[c:11]:[#7;a:12])-[C:13]>>[#7;a:5]:[c:6]-[C:7](-[C:8])-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10](-[c:11]:[#7;a:12])-[C:13] | 91 | [{"value": 91.0, "product": "CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC1=C(C#N)C=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.6, "product": "CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC1=C(C#N)C=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure A: A solution of 3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (0.602 g, 2.25 mmol), α-bromo-o-tolunitrile (0.668 g, 3.41 mmol), KI (100 mg, 0.60 mmol), and DIPEA (0.80 mL, 4.59 mmol) in DMF (11 mL) was heated at 60° C. for 23 hours. Purification of the crude material by colu... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccncc1.C1CC[NH]CC1.c1ccncc1.c1ccccc1 | HBr | CN(C)C=O | null | null | Cc1cccnc1C1CCCC(c2ncccc2C)N1.N#Cc1ccccc1CBr>CN(C)C=O>Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccccc1C#N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-99bd945b17484da2b882e142999adcdf | CO.Cc1ccc(C(=O)O)cc1[N+](=O)[O-]>>COC(=O)c1ccc(C)c([N+](=O)[O-])c1 | CC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-].S(O)(O)(=O)=O.CO>>COC(C1=CC(=C(C=C1)C)[N+](=O)[O-])=O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1 | CO.Cc1ccc(C(=O)O)cc1[N+](=O)[O-] | COC(=O)c1ccc(C)c([N+](=O)[O-])c1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 97 | [{"value": 97.0, "product": "COC(C1=CC(=C(C=C1)C)[N+](=O)[O-])=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-methyl-3-nitrobenzoic acid (5.52 g, 30.5 mmol) in MeOH (100 mL) was added 98% sulfuric acid (2 mL) and the resultant mixture was refluxed overnight, then cooled to room temperature. The mixture was concentrated and the residue was dissolved in CH2Cl2 (50 mL) and water (20 mL). Solid Na2CO3 was added ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.Cc1ccc(C(=O)O)cc1[N+](=O)[O-]>>COC(=O)c1ccc(C)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4d5cc9c759a04a9da593bc4c28b37f28 | COC(=O)c1ccc(C)c([N+](=O)[O-])c1.O=C1CCC(=O)N1Br>>COC(=O)c1ccc(CBr)c([N+](=O)[O-])c1 | N(=NC1(CCCCC1)C#N)C1(CCCCC1)C#N.COC(C1=CC(=C(C=C1)C)[N+](=O)[O-])=O.BrN1C(CCC1=O)=O>>COC(C1=CC(=C(C=C1)CBr)[N+](=O)[O-])=O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH3:9])[c:11]([N+:12](=[O:13])[O-:14])[cH:15]1.O=C1CCC(=O)N1[Br:10]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][Br:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15]1 | COC(=O)c1ccc(C)c([N+](=O)[O-])c1.O=C1CCC(=O)N1Br | COC(=O)c1ccc(CBr)c([N+](=O)[O-])c1 | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[CH3;D1;+0:2]-[c:3](:[c:4]):[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 61 | [{"value": 61.0, "product": "COC(C1=CC(=C(C=C1)CBr)[N+](=O)[O-])=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 61.0, "product": "COC(C1=CC(=C(C=C1)CBr)[N+](=O)[O-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-methyl-3-nitrobenzoic acid (5.52 g, 30.5 mmol) in MeOH (100 mL) was added 98% sulfuric acid (2 mL) and the resultant mixture was refluxed overnight, then cooled to room temperature. The mixture was concentrated and the residue was dissolved in CH2Cl2 (50 mL) and water (20 mL). Solid Na2CO3 was added ... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | COC(=O)c1ccc(C)c([N+](=O)[O-])c1.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>COC(=O)c1ccc(CBr)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9689d5366eb44f93b0738e4b5c2d797b | COC(=O)c1ccc(CBr)c([N+](=O)[O-])c1.Cc1cccnc1C1CCCC(c2ncccc2C)N1>>COC(=O)c1ccc(CN2C(c3ncccc3C)CCCC2c2ncccc2C)c([N+](=O)[O-])c1 | CC=1C(=NC=CC1)C1NC(CCC1)C1=NC=CC=C1C.COC(C1=CC(=C(C=C1)CBr)[N+](=O)[O-])=O.CCN(C(C)C)C(C)C>>COC(C1=CC(=C(C=C1)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C)[N+](=O)[O-])=O | Br[CH2:9][c:8]1[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:34][c:30]1[N+:31](=[O:32])[O-:33].[NH:10]1[CH:11]([c:12]2[n:13][cH:14][cH:15][cH:16][c:17]2[CH3:18])[CH2:19][CH2:20][CH2:21][CH:22]1[c:23]1[n:24][cH:25][cH:26][cH:27][c:28]1[CH3:29]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][N:10]2[CH:11]([c:... | COC(=O)c1ccc(CBr)c([N+](=O)[O-])c1.Cc1cccnc1C1CCCC(c2ncccc2C)N1 | COC(=O)c1ccc(CN2C(c3ncccc3C)CCCC2c2ncccc2C)c([N+](=O)[O-])c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2C(c3ccccn3)CCCC2c2ccccn2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]:[c:6]-[C:7](-[C:8])-[NH;D2;+0:9]-[C:10](-[c:11]:[#7;a:12])-[C:13]>>[#7;a:5]:[c:6]-[C:7](-[C:8])-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10](-[c:11]:[#7;a:12])-[C:13] | 98.1 | [{"value": 98.0, "product": "COC(C1=CC(=C(C=C1)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C)[N+](=O)[O-])=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 98.1, "product": "COC(C1=CC(=C(C=C1)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C)[N+](=O)[O-])=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure A: A solution of 3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (0.829 g, 3.10 mmol), 4-bromomethyl-3-nitrobenzoic acid methyl ester (1.26 g, 4.61 mmol), KI (115 mg, 0.69 mmol), and DIPEA (1.20 mL, 6.89 mmol) in DMF (16 mL) was heated at 60° C. for 18 hours. Purification of th... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HBr | CN(C)C=O | null | null | COC(=O)c1ccc(CBr)c([N+](=O)[O-])c1.Cc1cccnc1C1CCCC(c2ncccc2C)N1>CN(C)C=O>COC(=O)c1ccc(CN2C(c3ncccc3C)CCCC2c2ncccc2C)c([N+](=O)[O-])c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-caedbfd91ed74b8fa4184a2c95b7f89d | COC(=O)c1ccc(CN2C(c3ncccc3C)CCCC2c2ncccc2C)c([N+](=O)[O-])c1>>COC(=O)c1ccc(CN2C(c3ncccc3C)CCCC2c2ncccc2C)c(N)c1 | COC(C1=CC(=C(C=C1)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C)[N+](=O)[O-])=O>>COC(C1=CC(=C(C=C1)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C)N)=O | O=[N+:31]([O-])[c:30]1[c:8]([CH2:9][N:10]2[CH:11]([c:12]3[n:13][cH:14][cH:15][cH:16][c:17]3[CH3:18])[CH2:19][CH2:20][CH2:21][CH:22]2[c:23]2[n:24][cH:25][cH:26][cH:27][c:28]2[CH3:29])[cH:7][cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:32]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]([CH2:9][N:10]2[CH:11]([c:12]3[n:13]... | COC(=O)c1ccc(CN2C(c3ncccc3C)CCCC2c2ncccc2C)c([N+](=O)[O-])c1 | COC(=O)c1ccc(CN2C(c3ncccc3C)CCCC2c2ncccc2C)c(N)c1 | null | [Pd] | CO.CCOC(=O)C | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccc(CN2C(c3ccccn3)CCCC2c2ccccn2)cc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | 69 | [{"value": 69.0, "product": "COC(C1=CC(=C(C=C1)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C)N)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 69.0, "product": "COC(C1=CC(=C(C=C1)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C)N)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure A: A solution of 3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (0.829 g, 3.10 mmol), 4-bromomethyl-3-nitrobenzoic acid methyl ester (1.26 g, 4.61 mmol), KI (115 mg, 0.69 mmol), and DIPEA (1.20 mL, 6.89 mmol) in DMF (16 mL) was heated at 60° C. for 18 hours. Purification of th... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | Other | [Pd].CO.CCOC(=O)C | null | null | COC(=O)c1ccc(CN2C(c3ncccc3C)CCCC2c2ncccc2C)c([N+](=O)[O-])c1>[Pd].CO.CCOC(=O)C>COC(=O)c1ccc(CN2C(c3ncccc3C)CCCC2c2ncccc2C)c(N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5b98b66900a94a9a9fc3531729dcd456 | COC(=O)c1ccccc1C.O=C1CCC(=O)N1Br>>COC(=O)c1ccccc1CBr | N(=NC1(CCCCC1)C#N)C1(CCCCC1)C#N.COC(C1=C(C=CC=C1)C)=O.BrN1C(CCC1=O)=O>>COC(C1=C(C=CC=C1)CBr)=O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH3:11].O=C1CCC(=O)N1[Br:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][cH:8][cH:9][c:10]1[CH2:11][Br:12] | COC(=O)c1ccccc1C.O=C1CCC(=O)N1Br | COC(=O)c1ccccc1CBr | null | null | C(Cl)(Cl)(Cl)Cl | Functional Group Interconversion | Wohl-Ziegler bromination benzyl primary | 45c0aca0d63a96f0092e6dded9c888827eaf6379dac179e1cefc99293896300a | 08f5e7e34d3f321cce3e85421b38226d6240cca0939494ae61032d4f8405cf22 | c1ccccc1 | O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1].[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[CH3;D1;+0:7]):[c:8]>>[#8:2]-[C:3](=[O;D1;H0:4])-[c:5]:[c:6](-[CH2;D2;+0:7]-[Br;H0;D1;+0:1]):[c:8] | 78 | [{"value": 78.0, "product": "COC(C1=C(C=CC=C1)CBr)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 77.9, "product": "COC(C1=C(C=CC=C1)CBr)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2-methyl-benzoic acid methyl ester (4.58 g, 30.5 mmol) in CCl4 (75 mL) was added N-bromosuccinimide (5.79 g, 32.5 mmol) followed by 1,1′-azobis(cyclohexanecarbonitrile) (1.42 g, 5.80 mmol). The resultant mixture was refluxed for 6 hours then cooled to room temperature, filtered through filter paper, an... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amide.Tertiary amide | Primary halide | C1CCNC1 | null | c1ccccc1 | HO- | C(Cl)(Cl)(Cl)Cl | null | null | COC(=O)c1ccccc1C.O=C1CCC(=O)N1Br>C(Cl)(Cl)(Cl)Cl>COC(=O)c1ccccc1CBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ac3d2913dff2459bb6045f47cb02c8fc | CC(=O)c1ccccc1C.O=C1CCC(=O)N1Br.OCCO>>CC1(c2ccccc2CBr)OCCO1 | BrN1C(CCC1=O)=O.CC1=C(C=CC=C1)C(C)=O.C(CO)O.N(=NC1(CCCCC1)C#N)C1(CCCCC1)C#N.O.C1(=CC=C(C=C1)S(=O)(=O)O)C>>BrCC1=C(C=CC=C1)C1(OCCO1)C | [CH3:1][C:2]([c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[CH3:9])=[O:11].O=C1CCC(=O)N1[Br:10].O[CH2:12][CH2:13][OH:14]>>[CH3:1][C:2]1([c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[CH2:9][Br:10])[O:11][CH2:12][CH2:13][O:14]1 | CC(=O)c1ccccc1C.O=C1CCC(=O)N1Br.OCCO | CC1(c2ccccc2CBr)OCCO1 | null | null | C1=CC=CC=C1.CCOCC | Heteroatom Alkylation and Arylation | OtherReaction | a600dedac1763c4f45af318938e18604b2fdb48d7ca40a6c88d35b0267d63357 | 2c0d9125c7e823dfb9df94c919dfb6803a7f1b063007b4bd723c966af137913c | c1ccc(C2OCCO2)cc1 | O-[CH2;D2;+0:1]-[C:2]-[OH;D1;+0:3].O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:4].[C;D1;H3:5]-[C;H0;D3;+0:6](=[O;H0;D1;+0:7])-[c:8](:[c:9]):[c:10](-[CH3;D1;+0:11]):[c:12]>>[Br;H0;D1;+0:4]-[CH2;D2;+0:11]-[c:10](:[c:12]):[c:8](-[C;H0;D4;+0:6]1(-[C;D1;H3:5])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2]-[O;H0;D2;+0:3]-1):[c:9] | 80 | [{"value": 80.0, "product": "BrCC1=C(C=CC=C1)C1(OCCO1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 79.5, "product": "BrCC1=C(C=CC=C1)C1(OCCO1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 2′-methyl-acetophenone (2.68 g, 20.0 mmol) in benzene (100 mL) was added ethylene glycol (2.0 mL, 35.9 mmol) followed by p-toluenesulfonic acid monohydrate (0.39 g, 2.10 mmol). The reaction flask was topped with a Dean-Stark trap, and the mixture was heated to reflux overnight. The mixture was cooled t... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Tertiary amide.Tertiary amide.Primary alcohol.Primary alcohol | Primary halide.Ether.Ether | C1CCNC1 | C1COCO1 | c1ccccc1.C1COCO1 | HO- | C1=CC=CC=C1.CCOCC | null | null | CC(=O)c1ccccc1C.O=C1CCC(=O)N1Br.OCCO>C1=CC=CC=C1.CCOCC>CC1(c2ccccc2CBr)OCCO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5a8d13c7819d4a7bbf64af0122245ff7 | CC1(c2ccccc2CBr)OCCO1.Cc1cccnc1C1CCCC(c2ncccc2C)N1>>Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccccc1C1(C)OCCO1 | CC=1C(=NC=CC1)C1NC(CCC1)C1=NC=CC=C1C.BrCC1=C(C=CC=C1)C1(OCCO1)C.CCN(C(C)C)C(C)C>>CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC1=C(C=CC=C1)C1(OCCO1)C | Br[CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][c:27]1[C:28]1([CH3:29])[O:30][CH2:31][CH2:32][O:33]1.[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[CH3:19])[NH:20]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([... | CC1(c2ccccc2CBr)OCCO1.Cc1cccnc1C1CCCC(c2ncccc2C)N1 | Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccccc1C1(C)OCCO1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(C2CCCC(c3ccccn3)N2Cc2ccccc2C2OCCO2)nc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]:[c:6]-[C:7](-[C:8])-[NH;D2;+0:9]-[C:10](-[c:11]:[#7;a:12])-[C:13]>>[#7;a:5]:[c:6]-[C:7](-[C:8])-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10](-[c:11]:[#7;a:12])-[C:13] | 90 | [{"value": 90.0, "product": "CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC1=C(C=CC=C1)C1(OCCO1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 89.5, "product": "CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC1=C(C=CC=C1)C1(OCCO1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure A: A solution of 3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (0.547 g, 2.04 mmol), 2-(2-bromomethyl-phenyl)-2-methyl-[1,3]dioxolane (1.03 g, 3.99 mmol), KI (73 mg, 0.42 mmol), and DIPEA (0.70 mL, 4.02 mmol) in DMF (10 mL) was heated at 60° C. for 24 hours. Purification of t... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccncc1.C1CC[NH]CC1.c1ccncc1.c1ccccc1.C1COCO1 | HBr | CN(C)C=O | null | null | CC1(c2ccccc2CBr)OCCO1.Cc1cccnc1C1CCCC(c2ncccc2C)N1>CN(C)C=O>Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccccc1C1(C)OCCO1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a62703f2863846e6afd6ff32984ed4ec | Cc1cccnc1C1CCCC(c2ncccc2C)N1.N#Cc1ccc(CBr)cc1>>Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccc(C#N)cc1 | CC=1C(=NC=CC1)C1NC(CCC1)C1=NC=CC=C1C.BrCC1=CC=C(C=C1)C#N.CCN(C(C)C)C(C)C>>CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC1=CC=C(C#N)C=C1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[CH3:19])[NH:20]1.Br[CH2:21][c:22]1[cH:23][cH:24][c:25]([C:26]#[N:27])[cH:28][cH:29]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH:15][cH:16][cH:1... | Cc1cccnc1C1CCCC(c2ncccc2C)N1.N#Cc1ccc(CBr)cc1 | Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccc(C#N)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2C(c3ccccn3)CCCC2c2ccccn2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]:[c:6]-[C:7](-[C:8])-[NH;D2;+0:9]-[C:10](-[c:11]:[#7;a:12])-[C:13]>>[#7;a:5]:[c:6]-[C:7](-[C:8])-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10](-[c:11]:[#7;a:12])-[C:13] | 94.3 | [{"value": 94.0, "product": "CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC1=CC=C(C#N)C=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 94.3, "product": "CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC1=CC=C(C#N)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure A: A solution of 3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (0.502 g, 1.83 mmol), α-bromo-p-tolunitrile (0.538 g, 2.75 mmol), KI (65 mg, 0.40 mmol), and DIPEA (0.72 mL, 4.13 mmol) in DMF (9 mL) was heated at 60° C. for 16 hours. Purification of the crude material by column... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccncc1.C1CC[NH]CC1.c1ccncc1.c1ccccc1 | HBr | CN(C)C=O | null | null | Cc1cccnc1C1CCCC(c2ncccc2C)N1.N#Cc1ccc(CBr)cc1>CN(C)C=O>Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccc(C#N)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-a362150b2d8c47d9b50a079bd6b19fe2 | Cc1cccnc1C1CCCC(c2ncccc2C)N1.N#Cc1cccc(CBr)c1>>Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1cccc(C#N)c1 | CC=1C(=NC=CC1)C1NC(CCC1)C1=NC=CC=C1C.BrCC1=CC(=CC=C1)C#N.CCN(C(C)C)C(C)C>>CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC=1C=C(C#N)C=CC1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[CH3:19])[NH:20]1.Br[CH2:21][c:22]1[cH:23][cH:24][cH:25][c:26]([C:27]#[N:28])[cH:29]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH:15][cH:16][cH:1... | Cc1cccnc1C1CCCC(c2ncccc2C)N1.N#Cc1cccc(CBr)c1 | Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1cccc(C#N)c1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2C(c3ccccn3)CCCC2c2ccccn2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[#7;a:5]:[c:6]-[C:7](-[C:8])-[NH;D2;+0:9]-[C:10](-[c:11]:[#7;a:12])-[C:13]>>[#7;a:5]:[c:6]-[C:7](-[C:8])-[N;H0;D3;+0:9](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4])-[C:10](-[c:11]:[#7;a:12])-[C:13] | 75.4 | [{"value": 75.0, "product": "CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC=1C=C(C#N)C=CC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 75.4, "product": "CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC=1C=C(C#N)C=CC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure A: A solution of 3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (0.414 g, 1.55 mmol), α-bromo-m-tolunitrile (0.466 g, 2.38 mmol), KI (53 mg, 0.32 mmol), and DIPEA (0.55 mL, 3.16 mmol) in DMF (8 mL) was heated at 60° C. for 18 hours. Purification of the crude material by column... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccncc1.C1CC[NH]CC1.c1ccncc1.c1ccccc1 | HBr | CN(C)C=O | null | null | Cc1cccnc1C1CCCC(c2ncccc2C)N1.N#Cc1cccc(CBr)c1>CN(C)C=O>Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1cccc(C#N)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ec4f0cfe78cd47c59b3f817a1665ac00 | COC(=O)c1ccc(CN2C(c3ncccc3C)CCCC2c2ncccc2C)cc1>>Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccc(C(=O)O)cc1 | COC(C1=CC=C(C=C1)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C)=O.O.[OH-].[Na+].Cl>>CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC1=CC=C(C(=O)O)C=C1 | C[O:28][C:26]([c:25]1[cH:24][cH:23][c:22]([CH2:21][N:20]2[CH:8]([c:7]3[c:2]([CH3:1])[cH:3][cH:4][cH:5][n:6]3)[CH2:9][CH2:10][CH2:11][CH:12]2[c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[CH3:19])[cH:30][cH:29]1)=[O:27]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH:15][cH:1... | COC(=O)c1ccc(CN2C(c3ncccc3C)CCCC2c2ncccc2C)cc1 | Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccc(C(=O)O)cc1 | null | null | CO | Deprotection | Ester saponification (methyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(CN2C(c3ccccn3)CCCC2c2ccccn2)cc1 | C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]>>[O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4] | 108.5 | [{"value": 108.5, "product": "CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC1=CC=C(C(=O)O)C=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-benzoic acid methyl ester (0.420 g, 1.01 mmol) in MeOH (5 mL) was added water (5 mL) and solid NaOH (0.448 g, 11.21 mmol). The resultant mixture was heated to reflux overnight then cooled to room temperature. The mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccncc1.C1CC[NH]CC1.c1ccncc1.c1ccccc1 | Other | CO | null | null | COC(=O)c1ccc(CN2C(c3ncccc3C)CCCC2c2ncccc2C)cc1>CO>Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccc(C(=O)O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-53957fe214f7449597c1405a3df69165 | CCOC(=O)CCCCCBr.Cc1cccnc1[C@@H]1CCC[C@H](c2ncccc2C)N1>>CCOC(=O)CCCCCN1[C@@H](c2ncccc2C)CCC[C@H]1c1ncccc1C | CC=1C(=NC=CC1)[C@@H]1N[C@@H](CCC1)C1=NC=CC=C1C.C(C)OC(CCCCCBr)=O.CCN(C(C)C)C(C)C>>C(C)OC(CCCCCN1[C@H](CCC[C@H]1C1=NC=CC=C1C)C1=NC=CC=C1C)=O | Br[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH:11]1[C@H:12]([c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[CH3:19])[CH2:20][CH2:21][CH2:22][C@@H:23]1[c:24]1[n:25][cH:26][cH:27][cH:28][c:29]1[CH3:30]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C@@H:12]([c:13]2[n:14... | CCOC(=O)CCCCCBr.Cc1cccnc1[C@@H]1CCC[C@H](c2ncccc2C)N1 | CCOC(=O)CCCCCN1[C@@H](c2ncccc2C)CCC[C@H]1c1ncccc1C | null | null | CC#N | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc([C@@H]2CCC[C@H](c3ccccn3)N2)nc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]:[c:5]-[C:6](-[C:7])-[NH;D2;+0:8]-[C:9](-[c:10]:[#7;a:11])-[C:12]>>[#7;a:4]:[c:5]-[C:6](-[C:7])-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:9](-[c:10]:[#7;a:11])-[C:12] | 90.2 | [{"value": 90.0, "product": "C(C)OC(CCCCCN1[C@H](CCC[C@H]1C1=NC=CC=C1C)C1=NC=CC=C1C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 90.2, "product": "C(C)OC(CCCCCN1[C@H](CCC[C@H]1C1=NC=CC=C1C)C1=NC=CC=C1C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 23 | HOUR | A solution of (2′R,6′S)-3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (308 mg, 1.15 mmol), 6-bromo-hexanoic acid ethyl ester (283 mg, 1.27 mmol), DIPEA (260 μL, 1.49 mmol) and KI (10 mg, 0.060 mmol) in CH3CN (12 mL) was warmed to 60° C. and stirred for 23 h according to General Procedure A. Purifica... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccncc1.c1ccncc1 | HBr | CC#N | null | 23 | CCOC(=O)CCCCCBr.Cc1cccnc1[C@@H]1CCC[C@H](c2ncccc2C)N1>CC#N>CCOC(=O)CCCCCN1[C@@H](c2ncccc2C)CCC[C@H]1c1ncccc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a8d6f2890094fde847fcfbd5892dbb6 | COC(=O)c1cc(C#N)ccc1CBr.Clc1cccnc1C1CCCC(c2ncccc2Cl)N1>>COC(=O)c1cc(C#N)ccc1CN1C(c2ncccc2Cl)CCCC1c1ncccc1Cl | ClC=1C(=NC=CC1)C1NC(CCC1)C1=NC=CC=C1Cl.COC(C1=C(C=CC(=C1)C#N)CBr)=O.CCN(C(C)C)C(C)C>>COC(C1=C(C=CC(=C1)C#N)CN1C(CCCC1C1=NC=CC=C1Cl)C1=NC=CC=C1Cl)=O | Br[CH2:13][c:12]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:6][c:7]([C:8]#[N:9])[cH:10][cH:11]1.[NH:14]1[CH:15]([c:16]2[n:17][cH:18][cH:19][cH:20][c:21]2[Cl:22])[CH2:23][CH2:24][CH2:25][CH:26]1[c:27]1[n:28][cH:29][cH:30][cH:31][c:32]1[Cl:33]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([C:8]#[N:9])[cH:10][cH:11][c:12]1[CH2:13]... | COC(=O)c1cc(C#N)ccc1CBr.Clc1cccnc1C1CCCC(c2ncccc2Cl)N1 | COC(=O)c1cc(C#N)ccc1CN1C(c2ncccc2Cl)CCCC1c1ncccc1Cl | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(CN2C(c3ccccn3)CCCC2c2ccccn2)cc1 | Br-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7].[#7;a:8]:[c:9]-[C:10](-[C:11])-[NH;D2;+0:12]-[C:13](-[c:14]:[#7;a:15])-[C:16]>>[#7;a:8]:[c:9]-[C:10](-[C:11])-[N;H0;D3;+0:12](-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4]-[C:5](-[#8:6])=[O;D1;H0:7])-[C:13](-[c:14]:[#7;a:15])-[C:16] | 82.3 | [{"value": 82.0, "product": "COC(C1=C(C=CC(=C1)C#N)CN1C(CCCC1C1=NC=CC=C1Cl)C1=NC=CC=C1Cl)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.3, "product": "COC(C1=C(C=CC(=C1)C#N)CN1C(CCCC1C1=NC=CC=C1Cl)C1=NC=CC=C1Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure A: 3,3″-dichloro-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (304 mg, 0.987 mmol), 2-bromomethyl-5-cyano-benzoic acid methyl ester (351 mg, 1.38 mmol), KI (32.7 mg, 0.197 mmol), DIPEA (0.34 mL, 1.97 mmol), and DMF (5 mL) were stirred at 60° C. for 3 h. Purification of the crude material ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | HBr | CN(C)C=O | null | null | COC(=O)c1cc(C#N)ccc1CBr.Clc1cccnc1C1CCCC(c2ncccc2Cl)N1>CN(C)C=O>COC(=O)c1cc(C#N)ccc1CN1C(c2ncccc2Cl)CCCC1c1ncccc1Cl |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-65a609bf873e4f87ae8f56f5fee6f767 | COC(=O)c1cc(C#N)ccc1CN1C(c2ncccc2Cl)CCCC1c1ncccc1Cl>>N#Cc1ccc(CN2C(c3ncccc3Cl)CCCC2c2ncccc2Cl)c(CO)c1 | COC(C1=C(C=CC(=C1)C#N)CN1C(CCCC1C1=NC=CC=C1Cl)C1=NC=CC=C1Cl)=O.[Li+].[BH4-]>>ClC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1Cl)CC1=C(C=C(C#N)C=C1)CO | CO[C:29]([c:28]1[c:6]([CH2:7][N:8]2[CH:9]([c:10]3[n:11][cH:12][cH:13][cH:14][c:15]3[Cl:16])[CH2:17][CH2:18][CH2:19][CH:20]2[c:21]2[n:22][cH:23][cH:24][cH:25][c:26]2[Cl:27])[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:31]1)=[O:30]>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]2[CH:9]([c:10]3[n:11][cH:12][cH:13][cH:14][c:15]3[Cl:... | COC(=O)c1cc(C#N)ccc1CN1C(c2ncccc2Cl)CCCC1c1ncccc1Cl | N#Cc1ccc(CN2C(c3ncccc3Cl)CCCC2c2ncccc2Cl)c(CO)c1 | null | null | CO.[OH-].[Na+].C1CCOC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc(CN2C(c3ccccn3)CCCC2c2ccccn2)cc1 | C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c:3](:[c:4]):[c:5]>>[OH;D1;+0:2]-[CH2;D2;+0:1]-[c:3](:[c:4]):[c:5] | 99.6 | [{"value": 99.6, "product": "ClC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1Cl)CC1=C(C=C(C#N)C=C1)CO", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3.5 | HOUR | To a cold (0° C.) solution of 5-cyano-2-(3,3″-dichloro-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-benzoic acid methyl ester (391 mg, 0.813 mmol) in THF (4 mL) and MeOH (4 mL) was added LiBH4 (88 mg, 4.1 mmol), and the mixture was warmed to room temperature and stirred for 3.5 h. The mixture was dilu... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.c1ccncc1.C1CC[NH]CC1.c1ccncc1 | Other | CO.[OH-].[Na+].C1CCOC1 | null | 3.5 | COC(=O)c1cc(C#N)ccc1CN1C(c2ncccc2Cl)CCCC1c1ncccc1Cl>CO.[OH-].[Na+].C1CCOC1>N#Cc1ccc(CN2C(c3ncccc3Cl)CCCC2c2ncccc2Cl)c(CO)c1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5e18d3597c814e759d3eb303dda0f79f | BrCCCBr.c1c[nH]cn1>>BrCCCn1ccnc1 | N1C=NC=C1.BrCCCBr.[H-].[Na+]>>BrCCCN1C=NC=C1 | Br[CH2:4][CH2:3][CH2:2][Br:1].[nH:5]1[cH:6][cH:7][n:8][cH:9]1>>[Br:1][CH2:2][CH2:3][CH2:4][n:5]1[cH:6][cH:7][n:8][cH:9]1 | BrCCCBr.c1c[nH]cn1 | BrCCCn1ccnc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1c[nH]cn1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]1:[c:5]:[c:6]:[nH;D2;+0:7]:[c:8]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[#7;a:4]:[c:8]:1 | 30 | [{"value": 30.0, "product": "BrCCCN1C=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a stirred solution of imidazole (500 mg, 7.35 mmol) and 1,3-dibromopropane (2.2 mL, 22.0) in THF (35 mL) was added 60% NaH (356 mg, 8.82 mmol), and the resultant mixture was refluxed for 1 h and stirred at room temperature overnight. The mixture was quenched with H2O (25 mL) and diluted with CH2Cl2 (40 mL). The aque... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1 | HBr | C1CCOC1 | null | 8 | BrCCCBr.c1c[nH]cn1>C1CCOC1>BrCCCn1ccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-9a2add3353b24f71a4bf49219117e507 | BrCCCn1ccnc1.Cc1cccnc1C1CCCC(c2ncccc2C)N1>>Cc1cccnc1C1CCCC(c2ncccc2C)N1CCCn1ccnc1 | CC=1C(=NC=CC1)C1NC(CCC1)C1=NC=CC=C1C.BrCCCN1C=NC=C1.CCN(C(C)C)C(C)C>>N1(C=NC=C1)CCCN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C | Br[CH2:21][CH2:22][CH2:23][n:24]1[cH:25][cH:26][n:27][cH:28]1.[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[CH3:19])[NH:20]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH:15][cH:16][cH:17][c:1... | BrCCCn1ccnc1.Cc1cccnc1C1CCCC(c2ncccc2C)N1 | Cc1cccnc1C1CCCC(c2ncccc2C)N1CCCn1ccnc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(C2CCCC(c3ccccn3)N2CCCn2ccnc2)nc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]:[c:5]-[C:6](-[C:7])-[NH;D2;+0:8]-[C:9](-[c:10]:[#7;a:11])-[C:12]>>[#7;a:4]:[c:5]-[C:6](-[C:7])-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:9](-[c:10]:[#7;a:11])-[C:12] | 38 | [{"value": 38.0, "product": "N1(C=NC=C1)CCCN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 37.5, "product": "N1(C=NC=C1)CCCN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using General Procedure A: 3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (91.3 mg, 0.341 mmol), 1-(3-bromo-propyl)-1H-imidazole (129 mg, 0.680 mmol), KI (5.6 mg, 0.034 mmol), DIPEA (0.18 mL, 1.02 mmol), and DMF (3.4 mL) were stirred at 60° C. overnight. Purification of the crude material by flash ch... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccncc1.C1CC[NH]CC1.c1ccncc1.c1c[nH]cn1 | HBr | CN(C)C=O | null | null | BrCCCn1ccnc1.Cc1cccnc1C1CCCC(c2ncccc2C)N1>CN(C)C=O>Cc1cccnc1C1CCCC(c2ncccc2C)N1CCCn1ccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-453460d0a36d41198be5545bdce21d62 | BrCCCCBr.c1c[nH]cn1>>BrCCCCn1ccnc1 | N1C=NC=C1.BrCCCCBr.[H-].[Na+]>>BrCCCCN1C=NC=C1 | Br[CH2:5][CH2:4][CH2:3][CH2:2][Br:1].[nH:6]1[cH:7][cH:8][n:9][cH:10]1>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][n:6]1[cH:7][cH:8][n:9][cH:10]1 | BrCCCCBr.c1c[nH]cn1 | BrCCCCn1ccnc1 | null | null | C1CCOC1 | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | b9d84e1ee028da6e8c5d8924d45fbf8f3755d9adc2caf0035bd5ed7f30f5ee03 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | c1c[nH]cn1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]1:[c:5]:[nH;D2;+0:6]:[c:7]:[c:8]:1>>[C:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:6]1:[c:5]:[#7;a:4]:[c:8]:[c:7]:1 | null | [] | null | null | 8 | HOUR | To a stirred solution of imidazole (500 mg, 7.35 mmol) and 1,4-dibromobutane (2.6 mL, 22.0) in THF (50 mL) was added 60% NaH (356 mg, 8.81 mmol), and the resultant mixture was refluxed for 2 h and stirred at room temperature overnight. The mixture was quenched with H2O (50 mL) and diluted with CH2Cl2 (75 mL). The aqueo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1c[nH]cn1 | c1c[nH]cn1 | c1c[nH]cn1 | HBr | C1CCOC1 | null | 8 | BrCCCCBr.c1c[nH]cn1>C1CCOC1>BrCCCCn1ccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-e6270c35b1aa4c4d8815b6b30c1cf727 | BrCCCCn1ccnc1.Cc1cccnc1C1CCCC(c2ncccc2C)N1>>Cc1cccnc1C1CCCC(c2ncccc2C)N1CCCCn1ccnc1 | CC=1C(=NC=CC1)C1NC(CCC1)C1=NC=CC=C1C.BrCCCCN1C=NC=C1.CCN(C(C)C)C(C)C>>N1(C=NC=C1)CCCCN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C | Br[CH2:21][CH2:22][CH2:23][CH2:24][n:25]1[cH:26][cH:27][n:28][cH:29]1.[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[CH3:19])[NH:20]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH:15][cH:16][cH... | BrCCCCn1ccnc1.Cc1cccnc1C1CCCC(c2ncccc2C)N1 | Cc1cccnc1C1CCCC(c2ncccc2C)N1CCCCn1ccnc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 0240b8450ff2c489d02f5f0d90bc953079d7a3ab239d35a03f26392fc248b4ef | 523d37155b42c8dc851abeddadebb241cdd90bdf649ba750c35e13c8c752d7b0 | c1ccc(C2CCCC(c3ccccn3)N2CCCCn2ccnc2)nc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[#7;a:4]:[c:5]-[C:6](-[C:7])-[NH;D2;+0:8]-[C:9](-[c:10]:[#7;a:11])-[C:12]>>[#7;a:4]:[c:5]-[C:6](-[C:7])-[N;H0;D3;+0:8](-[CH2;D2;+0:1]-[C:2]-[C:3])-[C:9](-[c:10]:[#7;a:11])-[C:12] | 34.2 | [{"value": 34.0, "product": "N1(C=NC=C1)CCCCN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.2, "product": "N1(C=NC=C1)CCCCN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a stirred solution of imidazole (500 mg, 7.35 mmol) and 1,4-dibromobutane (2.6 mL, 22.0) in THF (50 mL) was added 60% NaH (356 mg, 8.81 mmol), and the resultant mixture was refluxed for 2 h and stirred at room temperature overnight. The mixture was quenched with H2O (50 mL) and diluted with CH2Cl2 (75 mL). The aqueo... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccncc1.C1CC[NH]CC1.c1ccncc1.c1c[nH]cn1 | HBr | CN(C)C=O | null | null | BrCCCCn1ccnc1.Cc1cccnc1C1CCCC(c2ncccc2C)N1>CN(C)C=O>Cc1cccnc1C1CCCC(c2ncccc2C)N1CCCCn1ccnc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-b6e38debdb4e4f89bdadcddf63a58b91 | CO.O=C(O)Cc1c[nH]cn1>>COC(=O)Cc1c[nH]cn1 | Cl.N1C=NC(=C1)CC(=O)O.S(O)(O)(=O)=O.CO>>COC(CC=1N=CNC1)=O | [CH3:1][OH:2].O[C:3](=[O:4])[CH2:5][c:6]1[cH:7][nH:8][cH:9][n:10]1>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][nH:8][cH:9][n:10]1 | CO.O=C(O)Cc1c[nH]cn1 | COC(=O)Cc1c[nH]cn1 | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1c[nH]cn1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[c:4](:[#7;a:5]):[c:6]:[#7;a:7].[C;D1;H3:8]-[OH;D1;+0:9]>>[#7;a:5]:[c:4](-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[O;H0;D2;+0:9]-[C;D1;H3:8]):[c:6]:[#7;a:7] | 66 | [{"value": 66.0, "product": "COC(CC=1N=CNC1)=O", "details": "PERCENTYIELD", "is_desired": false}] | 80 | CELSIUS | null | null | To a solution of 4-imidazoleacetic acid hydrochloride (499 mg, 3.07 mmol) in MeOH (10 mL) was added concentrated sulfuric acid (1 mL) and the mixture was heated to 80° C. overnight. Then the mixture was cooled and concentrated. The residue was dissolved in CH2Cl2 (30 mL) and washed with saturated NaHCO3 (30 mL). The aq... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1c[nH]cn1 | HO- | null | 80 | null | CO.O=C(O)Cc1c[nH]cn1>>COC(=O)Cc1c[nH]cn1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-8e7597cbdb5847fba435581e46e3fceb | CO.Cc1ccc(F)cc1C(=O)O>>COC(=O)c1cc(F)ccc1C | FC=1C=CC(=C(C(=O)O)C1)C.CO.OS(=O)(=O)O>>COC(C1=C(C=CC(=C1)F)C)=O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]1[CH3:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]1[CH3:12] | CO.Cc1ccc(F)cc1C(=O)O | COC(=O)c1cc(F)ccc1C | null | null | null | Protection | Esterification of Carboxylic Acids | 9cecdbd189c6f9c3648521d17154d013842a5498de4e76e65efb1d842973340b | af0b8064f2e82ebe66c4c29d2391785ac1b993104265ccdc4d67ca79e36fa3c8 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | 78 | [{"value": 78.0, "product": "COC(C1=C(C=CC(=C1)F)C)=O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | 5-Fluoro-2-methyl-benzoic acid (0.29 g, 1.9 mmol) was dissolved in anhydrous MeOH (7 mL) and c. H2SO4 (0.12 mL, 2.3 mmol) was added, heating to reflux for 16 hours. The solution was cooled to room temperature and partitioned between EtOAc (15 mL) and brine (10 mL). After separating, the aqueous phase was extracted with... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.Cc1ccc(F)cc1C(=O)O>>COC(=O)c1cc(F)ccc1C |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c4ce1ab8900c4a21ace0be056038e3b9 | Cc1ccc(S(=O)(=O)Cl)cc1.O=Cc1ncc[nH]1>>Cc1ccc(S(=O)(=O)n2ccnc2C=O)cc1 | N1C(=NC=C1)C=O.CCN(CC)CC.S(=O)(=O)(C1=CC=C(C)C=C1)Cl>>C1(=CC=C(C=C1)S(=O)(=O)N1C(=NC=C1)C=O)C | Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:17][cH:16]1)(=[O:7])=[O:8].[nH:9]1[cH:10][cH:11][n:12][c:13]1[CH:14]=[O:15]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][cH:11][n:12][c:13]2[CH:14]=[O:15])[cH:16][cH:17]1 | Cc1ccc(S(=O)(=O)Cl)cc1.O=Cc1ncc[nH]1 | Cc1ccc(S(=O)(=O)n2ccnc2C=O)cc1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 9d95b3f7a94155c15253f03a3d139421fdad476c6138a59a600798d164b552ae | b7cf703ff8ec1befb0c6e5230d29d7904f3e22c3606b15633c7e7a7fc4abca48 | O=S(=O)(c1ccccc1)n1ccnc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[O;D1;H0:7]=[C:8]-[c:9]1:[#7;a:10]:[c:11]:[c:12]:[nH;D2;+0:13]:1>>[O;D1;H0:7]=[C:8]-[c:9]1:[#7;a:10]:[c:11]:[c:12]:[n;H0;D3;+0:13]:1-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | 58.2 | [{"value": 58.0, "product": "C1(=CC=C(C=C1)S(=O)(=O)N1C(=NC=C1)C=O)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 58.2, "product": "C1(=CC=C(C=C1)S(=O)(=O)N1C(=NC=C1)C=O)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 2-imidazolecarboxaldehyde (1.01 g, 10.51 mmol) in CH2Cl2 (25 mL) was added Et3N (2.9 mL, 21.02 mmol) and tosyl chloride (3.01 g, 15.77 mmol) and the reaction mixture was heated to reflux overnight. Then the mixture was cooled and washed with saturated NH4Cl (4×30 mL). The organic layer was dried (MgS... | 10.6084/m9.figshare.5104873.v1 | null | Tosylate.Sulfonyl halide | Tosylate | c1c[nH]cn1 | c1ncc[nH]1 | c1ccccc1.c1ncc[nH]1 | HCl | C(Cl)Cl | null | null | Cc1ccc(S(=O)(=O)Cl)cc1.O=Cc1ncc[nH]1>C(Cl)Cl>Cc1ccc(S(=O)(=O)n2ccnc2C=O)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-1cccd055a88448d3bbd9dd847eaf0a80 | Cc1ccc(S(=O)(=O)n2ccnc2C=O)cc1>>Cc1ccc(S(=O)(=O)n2ccnc2CO)cc1 | C1(=CC=C(C=C1)S(=O)(=O)N1C(=NC=C1)C=O)C.C(=O)(C(F)(F)F)O>>C1(=CC=C(C=C1)S(=O)(=O)N1C(=NC=C1)CO)C | [CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][cH:11][n:12][c:13]2[CH:14]=[O:15])[cH:16][cH:17]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][cH:11][n:12][c:13]2[CH2:14][OH:15])[cH:16][cH:17]1 | Cc1ccc(S(=O)(=O)n2ccnc2C=O)cc1 | Cc1ccc(S(=O)(=O)n2ccnc2CO)cc1 | null | null | C(Cl)Cl | Reduction | Reduction of aldehydes and ketones to alcohols | e7895795cd3f75445716c94697823c5929dcd4b5344525875fe75d36bca2f9d7 | 21bb81d5469aaaca71ab12c186bea4016451717fad8780cf288858a7d8fbc55a | O=S(=O)(c1ccccc1)n1ccnc1 | [#16:1]-[#7;a:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[CH;D2;+0:7]=[O;H0;D1;+0:8]>>[#16:1]-[#7;a:2]1:[c:3]:[c:4]:[#7;a:5]:[c:6]:1-[CH2;D2;+0:7]-[OH;D1;+0:8] | 36 | [{"value": 36.0, "product": "C1(=CC=C(C=C1)S(=O)(=O)N1C(=NC=C1)CO)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.7, "product": "C1(=CC=C(C=C1)S(=O)(=O)N1C(=NC=C1)CO)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of the above aldehyde (1.53 g, 6.11 mmol) in CH2Cl2 (50 mL) at 0° C. was added TFA (5 mL) as described in J. Med. Chem. (1997) 40:2196. Purification by flash column chromatography using EtOAc/hexane (1:1) afforded [1-(toluene-4-sulfonyl)-1H-imidazol-2-yl]-methanol as a white solid (0.55 g, 36%). 1H NMR (C... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde | Primary alcohol | null | null | c1ccccc1.c1ncc[nH]1 | null | C(Cl)Cl | null | null | Cc1ccc(S(=O)(=O)n2ccnc2C=O)cc1>C(Cl)Cl>Cc1ccc(S(=O)(=O)n2ccnc2CO)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-00b8ffdb5a4049e29a7c27475c4f58f0 | BrC(Br)(Br)Br.Cc1ccc(S(=O)(=O)n2ccnc2CO)cc1>>Cc1ccc(S(=O)(=O)n2ccnc2CBr)cc1 | C1(=CC=C(C=C1)S(=O)(=O)N1C(=NC=C1)CO)C.C(Br)(Br)(Br)Br.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1>>BrCC=1N(C=CN1)S(=O)(=O)C1=CC=C(C=C1)C | BrC(Br)(Br)[Br:15].O[CH2:14][c:13]1[n:9]([S:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:17][cH:16]2)(=[O:7])=[O:8])[cH:10][cH:11][n:12]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][cH:11][n:12][c:13]2[CH2:14][Br:15])[cH:16][cH:17]1 | BrC(Br)(Br)Br.Cc1ccc(S(=O)(=O)n2ccnc2CO)cc1 | Cc1ccc(S(=O)(=O)n2ccnc2CBr)cc1 | null | null | C(Cl)Cl | Functional Group Interconversion | Appel reaction | 752e1807cd47d8316010cc3f92eab16c5a89ffb844d9514fcae469ba993c78dd | 2c6b51fb1e17cb2c93d565e0423c75825df2c8e11c870e0c98b278f20ba9f3ad | O=S(=O)(c1ccccc1)n1ccnc1 | Br-C(-Br)(-Br)-[Br;H0;D1;+0:1].O-[CH2;D2;+0:2]-[c:3]1:[#7;a:4]:[c:5]:[c:6]:[#7;a:7]:1-[#16:8]>>[#16:8]-[#7;a:7]1:[c:6]:[c:5]:[#7;a:4]:[c:3]:1-[CH2;D2;+0:2]-[Br;H0;D1;+0:1] | 45.3 | [{"value": 45.0, "product": "BrCC=1N(C=CN1)S(=O)(=O)C1=CC=C(C=C1)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 45.3, "product": "BrCC=1N(C=CN1)S(=O)(=O)C1=CC=C(C=C1)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of the above alcohol (0.55 g, 2.17 mmol) and CBr4 (1.08 g, 3.26 mmol) in CH2Cl2 (25 mL) at 0° C. was added a solution of triphenylphosphine (0.68 g, 2.60 mmol) in CH2Cl2 (10 mL) as described in J. Med. Chem. (1997) 40, 14:2196. Purification by flash column chromatography using 25% EtOAc/hexanes afforded 2... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary halide.Tertiary halide.Tertiary halide.Tertiary halide.Primary alcohol | Primary halide | null | null | c1ccccc1.c1ncc[nH]1 | HBr | C(Cl)Cl | null | null | BrC(Br)(Br)Br.Cc1ccc(S(=O)(=O)n2ccnc2CO)cc1>C(Cl)Cl>Cc1ccc(S(=O)(=O)n2ccnc2CBr)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-29461549a9f644e5a4b0db020a8a3439 | CCOC(=O)C1CCN(S(=O)(=O)c2ccc(C)cc2)CC1>>Cc1ccc(S(=O)(=O)N2CCC(CO)CC2)cc1 | C(C)OC(=O)C1CCN(CC1)S(=O)(=O)C1=CC=C(C=C1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1CCOC1>>C1(=CC=C(C=C1)S(=O)(=O)N1CCC(CC1)CO)C | CCO[C:13]([CH:12]1[CH2:11][CH2:10][N:9]([S:6]([c:5]2[cH:4][cH:3][c:2]([CH3:1])[cH:18][cH:17]2)(=[O:7])=[O:8])[CH2:16][CH2:15]1)=[O:14]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[N:9]2[CH2:10][CH2:11][CH:12]([CH2:13][OH:14])[CH2:15][CH2:16]2)[cH:17][cH:18]1 | CCOC(=O)C1CCN(S(=O)(=O)c2ccc(C)cc2)CC1 | Cc1ccc(S(=O)(=O)N2CCC(CO)CC2)cc1 | null | null | C(Cl)Cl | Functional Group Interconversion | Reduction of ester to primary alcohol | cd99347e3144bc4f081bc664a4bc5a11d1e392f7cea47a5adad92bcd498ccf56 | a2b5cf843cfeb048c76ac4cbf0bd8ccab026fcad80259b78e012cdb6ac2f5934 | O=S(=O)(c1ccccc1)N1CCCCC1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[C:3](-[C:4])-[C:5]>>[C:4]-[C:3](-[CH2;D2;+0:1]-[OH;D1;+0:2])-[C:5] | 100 | [{"value": 100.0, "product": "C1(=CC=C(C=C1)S(=O)(=O)N1CCC(CC1)CO)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.1, "product": "C1(=CC=C(C=C1)S(=O)(=O)N1CCC(CC1)CO)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a solution of the above ester (1.29 g, 4.79 mmol) in CH2Cl2 (20 mL) at 0° C. was added a solution of LiAlH4 in THF (1.0 M, 13.9 mL, 13.87 mmol) and the mixture was heated to reflux. After 1 h, the mixture was cooled back down to 0° C. and quenched with H2O (0.51 mL), 15% NaOH (0.51 mL), and H2O (1.53 mL). After stir... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1.C1CC[NH]CC1 | HO- | C(Cl)Cl | 0 | 1 | CCOC(=O)C1CCN(S(=O)(=O)c2ccc(C)cc2)CC1>C(Cl)Cl>Cc1ccc(S(=O)(=O)N2CCC(CO)CC2)cc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-c97fed26492e4b758945b9c149c8318a | Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccc(C#N)cc1CO>>Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccc(CN)cc1CO.[NH4+].[OH-] | CC=1C(=NC=CC1)C1N(C(CCC1)C1=NC=CC=C1C)CC1=C(C=C(C#N)C=C1)CO>>[NH4+].[OH-].NCC=1C=CC(=C(C1)CO)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C | [CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[CH3:19])[N:20]1[CH2:21][c:22]1[cH:23][cH:24][c:25]([C:26]#[N:27])[cH:28][c:29]1[CH2:30][OH:31]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH:15][c... | Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccc(C#N)cc1CO | Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccc(CN)cc1CO.[NH4+].[OH-] | null | null | CO | Functional Group Interconversion | Reduction of nitrile to amine | 3b047a13c16a607c445b1c419e256808e8c9a0097d8fb9efd4e7970deb782b70 | 2882e57127fc469aa16ca9a2fd53388b6d97c74c76c010e6eb01be5726f46aa5 | c1ccc(CN2C(c3ccccn3)CCCC2c2ccccn2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 175.2 | [{"value": 88.0, "product": "NCC=1C=CC(=C(C1)CO)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 175.2, "product": "NCC=1C=CC(=C(C1)CO)CN1C(CCCC1C1=NC=CC=C1C)C1=NC=CC=C1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2.5 | HOUR | To a solution of 4-(3,3″-dimethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-3-hydroxymethyl-benzonitrile (0.610 g, 1.48 mmol) dissolved in MeOH (12 mL) ammonia gas was bubbled for 10 minutes. A pre-washed mixture of Raney Nickel (˜1.5 grams) was added to the nitrile and the mixture was shaken on th... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccncc1.C1CC[NH]CC1.c1ccncc1.c1ccccc1 | Other | CO | null | 2.5 | Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccc(C#N)cc1CO>CO>Cc1cccnc1C1CCCC(c2ncccc2C)N1Cc1ccc(CN)cc1CO.[NH4+].[OH-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-bbe1a5193e8f44d29aac70cb11d77962 | Cc1cnc(C2CCCC(c3ncc(C)cc3C)N2Cc2ccc(C#N)cc2CO)c(C)c1>>Cc1cnc(C2CCCC(c3ncc(C)cc3C)N2Cc2ccc(CN)cc2CO)c(C)c1.[NH4+].[OH-] | OCC=1C=C(C#N)C=CC1CN1C(CCCC1C1=NC=C(C=C1C)C)C1=NC=C(C=C1C)C>>[NH4+].[OH-].NCC=1C=CC(=C(C1)CO)CN1C(CCCC1C1=NC=C(C=C1C)C)C1=NC=C(C=C1C)C | [CH3:1][c:2]1[cH:3][n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH:10]([c:11]3[n:12][cH:13][c:14]([CH3:15])[cH:16][c:17]3[CH3:18])[N:19]2[CH2:20][c:21]2[cH:22][cH:23][c:24]([C:25]#[N:26])[cH:27][c:28]2[CH2:29][OH:30])[c:31]([CH3:32])[cH:33]1>>[CH3:1][c:2]1[cH:3][n:4][c:5]([CH:6]2[CH2:7][CH2:8][CH2:9][CH:10]([c:11]3[n:12][cH... | Cc1cnc(C2CCCC(c3ncc(C)cc3C)N2Cc2ccc(C#N)cc2CO)c(C)c1 | Cc1cnc(C2CCCC(c3ncc(C)cc3C)N2Cc2ccc(CN)cc2CO)c(C)c1.[NH4+].[OH-] | null | null | CO | Functional Group Interconversion | Reduction of nitrile to amine | 3b047a13c16a607c445b1c419e256808e8c9a0097d8fb9efd4e7970deb782b70 | 2882e57127fc469aa16ca9a2fd53388b6d97c74c76c010e6eb01be5726f46aa5 | c1ccc(CN2C(c3ccccn3)CCCC2c2ccccn2)cc1 | [N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[NH2;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5] | 196 | [{"value": 99.0, "product": "NCC=1C=CC(=C(C1)CO)CN1C(CCCC1C1=NC=C(C=C1C)C)C1=NC=C(C=C1C)C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 196.0, "product": "NCC=1C=CC(=C(C1)CO)CN1C(CCCC1C1=NC=C(C=C1C)C)C1=NC=C(C=C1C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a solution of 3-hydroxymethyl-4-(3,5,3″,5″-tetramethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-ylmethyl)-benzonitrile (0.060 g, 0.14 mmol) dissolved in MeOH (7 mL) ammonia gas was bubbled for 10 minutes. A pre-washed mixture of Raney Nickel (˜0.5 gram) was added to the nitrile and the mixture was shaken... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amine | null | null | c1ccncc1.C1CC[NH]CC1.c1ccncc1.c1ccccc1 | Other | CO | null | 2 | Cc1cnc(C2CCCC(c3ncc(C)cc3C)N2Cc2ccc(C#N)cc2CO)c(C)c1>CO>Cc1cnc(C2CCCC(c3ncc(C)cc3C)N2Cc2ccc(CN)cc2CO)c(C)c1.[NH4+].[OH-] |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-f7865eb4f1c34d4ab6f6b5c5db4bdf57 | CC(C)(C)OC(=O)N1CC(CN)C1.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl>>O=[N+]([O-])c1ccccc1S(=O)(=O)N1CC(CO)C1 | C(=O)(C(F)(F)F)O.NCC1CN(C1)C(=O)OC(C)(C)C.CCN(C(C)C)C(C)C.[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)Cl>>[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)N1CC(C1)CO | CC(C)(C)[O:17]C(=O)[N:13]1[CH2:14][CH:15]([CH2:16]N)[CH2:18]1.Cl[S:10]([c:9]1[c:4]([N+:2](=[O:1])[O-:3])[cH:5][cH:6][cH:7][cH:8]1)(=[O:11])=[O:12]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[S:10](=[O:11])(=[O:12])[N:13]1[CH2:14][CH:15]([CH2:16][OH:17])[CH2:18]1 | CC(C)(C)OC(=O)N1CC(CN)C1.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl | O=[N+]([O-])c1ccccc1S(=O)(=O)N1CC(CO)C1 | null | null | C(Cl)Cl | Acylation | OtherReaction | c9b078a4caf5c997901165af10960ed437a356b37bb74fff6be2fea2cd04573f | ebabfd3fff10853cf77efe5d8ae3f9cc562ad656b1c42b39d1bbf247c8359ebc | O=S(=O)(c1ccccc1)N1CCC1 | C-C(-C)(-C)-[O;H0;D2;+0:1]-C(=O)-[N;H0;D3;+0:2]1-[C:3]-[C:4](-[CH2;D2;+0:5]-N)-[C:6]-1.Cl-[S;H0;D4;+0:7](=[O;D1;H0:8])(=[O;D1;H0:9])-[c:10](:[c:11]):[c:12]>>[O;D1;H0:8]=[S;H0;D4;+0:7](=[O;D1;H0:9])(-[N;H0;D3;+0:2]1-[C:3]-[C:4](-[CH2;D2;+0:5]-[OH;D1;+0:1])-[C:6]-1)-[c:10](:[c:11]):[c:12] | 26 | [{"value": 26.0, "product": "[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)N1CC(C1)CO", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | Tert-butyl 3-(aminomethyl)-1-azetidinecarboxylate (J. Med. Chem., (2001) 44:94-104) (441 mg, 2.35 mmol) was dissolved in CH2Cl2 (2 mL) and TFA (1.5 mL) and the mixture was stirred for 2 hours at room temperature. The volatiles were removed under reduced pressure and the residue was dissolved in dry MeOH (5 mL). Solid N... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Primary amine.Sulfonyl halide.Boc | Primary alcohol.Tertiary amine | C1C[NH]C1 | C1C[NH]C1 | c1ccccc1.C1C[NH]C1 | HCl | C(Cl)Cl | null | 17 | CC(C)(C)OC(=O)N1CC(CN)C1.O=[N+]([O-])c1ccccc1S(=O)(=O)Cl>C(Cl)Cl>O=[N+]([O-])c1ccccc1S(=O)(=O)N1CC(CO)C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-95b95e90c71f45ecbbe9619ba59fb7a4 | Cc1cccnc1C1NC(c2ccccn2)CCC1C.O=[N+]([O-])c1ccccc1S(=O)(=O)N1CC(CO)C1>>Cc1cccnc1C1C(C)CCC(c2ccccn2)N1CC1CN(S(=O)(=O)c2ccccc2[N+](=O)[O-])C1 | C(=O)(O)[O-].[Na+].[N+](=O)([O-])C1=C(C=CC=C1)S(=O)(=O)N1CC(C1)CO.CCN(CC)CC.CCN(C(C)C)C(C)C.CC=1C(=NC=CC1)C1NC(CCC1C)C1=NC=CC=C1.S(=O)(=O)(C)Cl>>CC=1C(=NC=CC1)C1N(C(CCC1C)C1=NC=CC=C1)CC1CN(C1)S(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-] | [CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH:9]([CH3:10])[CH2:11][CH2:12][CH:13]([c:14]2[cH:15][cH:16][cH:17][cH:18][n:19]2)[NH:20]1.O[CH2:21][CH:22]1[CH2:23][N:24]([S:25](=[O:26])(=[O:27])[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[N+:34](=[O:35])[O-:36])[CH2:37]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:... | Cc1cccnc1C1NC(c2ccccn2)CCC1C.O=[N+]([O-])c1ccccc1S(=O)(=O)N1CC(CO)C1 | Cc1cccnc1C1C(C)CCC(c2ccccn2)N1CC1CN(S(=O)(=O)c2ccccc2[N+](=O)[O-])C1 | null | null | CCOC(=O)C | Functional Group Addition | OtherReaction | f03f6c9202affca8ab5230edf5678122ee5f9bfd569dea4217eba5e24f74f1c9 | 1019cc59ab0f350ad0daefd56a772ded1fa308745fe5d7f2116c2a78fd535d58 | O=S(=O)(c1ccccc1)N1CC(CN2C(c3ccccn3)CCCC2c2ccccn2)C1 | O-[CH2;D2;+0:1]-[C:2]1-[C:3]-[#7:4]-[C:5]-1.[#7;a:6]:[c:7]-[C:8](-[C:9])-[NH;D2;+0:10]-[C:11](-[c:12]:[#7;a:13])-[C:14]>>[#7;a:6]:[c:7]-[C:8](-[C:9])-[N;H0;D3;+0:10](-[CH2;D2;+0:1]-[C:2]1-[C:3]-[#7:4]-[C:5]-1)-[C:11](-[c:12]:[#7;a:13])-[C:14] | 53.1 | [{"value": 53.0, "product": "CC=1C(=NC=CC1)C1N(C(CCC1C)C1=NC=CC=C1)CC1CN(C1)S(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "PERCENTYIELD", "is_desired": false}, {"value": 53.1, "product": "CC=1C(=NC=CC1)C1N(C(CCC1C)C1=NC=CC=C1)CC1CN(C1)S(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-]", "details": "CALCULATEDPERCENTYIELD", "is_desir... | null | null | 1 | HOUR | To a 0° C. solution of [1-(2-nitro-benzenesulfonyl)-azetidin-3-yl]-methanol (165 mg, 0.606 mmol) in EtOAc (15 mL) was added Et3N (0.101 mL, 0.727 mmol) then mesyl chloride (0.052 mL, 0.666 mmol). The reaction mixture was stirred for 1 hour at room temperature. The precipitate was filtered through a plug of Celite and w... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Secondary amine | Tertiary amine | C1CCNCC1 | C1CC[NH]CC1 | c1ccncc1.C1CC[NH]CC1.c1ccncc1.C1C[NH]C1.c1ccccc1 | HO- | CCOC(=O)C | null | 1 | Cc1cccnc1C1NC(c2ccccn2)CCC1C.O=[N+]([O-])c1ccccc1S(=O)(=O)N1CC(CO)C1>CCOC(=O)C>Cc1cccnc1C1C(C)CCC(c2ccccn2)N1CC1CN(S(=O)(=O)c2ccccc2[N+](=O)[O-])C1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-66f1a9641cb44e7daa1ddf8302288fe0 | Cc1cccnc1C1C(C)CCC(c2ccccn2)N1CC1CN(S(=O)(=O)c2ccccc2[N+](=O)[O-])C1>>c1ccc(C2CCCC(c3ccccn3)N2CC2CNC2)nc1 | CC=1C(=NC=CC1)C1N(C(CCC1C)C1=NC=CC=C1)CC1CN(C1)S(=O)(=O)C1=C(C=CC=C1)[N+](=O)[O-].C1(=CC=CC=C1)S.C(=O)([O-])[O-].[K+].[K+]>>N1CC(C1)CN1C(CCCC1C1=NC=CC=C1)C1=NC=CC=C1 | C[c:3]1[cH:2][cH:1][cH:23][n:22][c:4]1[CH:5]1[CH:6](C)[CH2:7][CH2:8][CH:9]([c:10]2[cH:11][cH:12][cH:13][cH:14][n:15]2)[N:16]1[CH2:17][CH:18]1[CH2:19][N:20](S(=O)(=O)c2ccccc2[N+](=O)[O-])[CH2:21]1>>[cH:1]1[cH:2][cH:3][c:4]([CH:5]2[CH2:6][CH2:7][CH2:8][CH:9]([c:10]3[cH:11][cH:12][cH:13][cH:14][n:15]3)[N:16]2[CH2:17][CH:1... | Cc1cccnc1C1C(C)CCC(c2ccccn2)N1CC1CN(S(=O)(=O)c2ccccc2[N+](=O)[O-])C1 | c1ccc(C2CCCC(c3ccccn3)N2CC2CNC2)nc1 | null | null | CC#N | Reduction | OtherReaction | 0bb4f82351d44fc53045df118d951e20c9995441f41cd68cf728d5a241ca8944 | 1e653e20ac001d92972e72ca6294e607303822683eea0adc1fa0a988ff7782b7 | c1ccc(C2CCCC(c3ccccn3)N2CC2CNC2)nc1 | C-[CH;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[#7:5](-[C:6]-[C:7]2-[C:8]-[N;H0;D3;+0:9](-S(=O)(=O)-c3:c:c:c:c:c:3-[N+](=O)-[O-])-[C:10]-2)-[C:11]-1-[c:12]1:[#7;a:13]:[c:14]:[c:15]:[c:16]:[c;H0;D3;+0:17]:1-C>>[#7;a:13]1:[c:14]:[c:15]:[c:16]:[cH;D2;+0:17]:[c:12]:1-[C:11]1-[CH2;D2;+0:1]-[C:2]-[C:3]-[C:4]-[#7:5]-1-[C:6]-[C:7]1-[C:8]-[... | 80 | [{"value": 80.0, "product": "N1CC(C1)CN1C(CCCC1C1=NC=CC=C1)C1=NC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 74.5, "product": "N1CC(C1)CN1C(CCCC1C1=NC=CC=C1)C1=NC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 17 | HOUR | A mixture of 3,3′-dimethyl-1′-[1-(2-nitro-benzenesulfonyl)-azetidin-3-ylmethyl]-1′,2′,3′4′,5′,6′-hexahydro-[2,2′;6′,2″]terpyridine (168 mg, 0.322 mmol), thiophenol (0.3 mL), K2CO3 (500 mg) in CH3CN (5 mL) were stirred at room temperature for 17 hours. The volatiles were removed under reduced pressure and saturated NaHC... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Tertiary amine | Secondary amine | c1ccncc1.C1CC[NH]CC1.C1C[NH]C1.c1ccccc1 | c1ccncc1.C1CC[NH]CC1.C1CNC1 | c1ccncc1.C1CC[NH]CC1.c1ccncc1.C1CNC1 | HO- | CC#N | null | 17 | Cc1cccnc1C1C(C)CCC(c2ccccn2)N1CC1CN(S(=O)(=O)c2ccccc2[N+](=O)[O-])C1>CC#N>c1ccc(C2CCCC(c3ccccn3)N2CC2CNC2)nc1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-5c5da8fd01ab4a5194e715aeb5dde30c | CC(Br)C(C)Br.O=C1NC(=O)c2ccccc21>>O=C1c2ccccc2C(=O)N1CCCCBr | O.BrC(C(C)Br)C.C1(C=2C(C(N1)=O)=CC=CC2)=O.[K].CN(C=O)C>>BrCCCCN1C(C2=CC=CC=C2C1=O)=O | Br[CH:14]([CH3:13])[CH:15]([CH3:12])[Br:16].[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[NH:11]1>>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][CH2:13][CH2:14][CH2:15][Br:16] | CC(Br)C(C)Br.O=C1NC(=O)c2ccccc21 | O=C1c2ccccc2C(=O)N1CCCCBr | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f628a96282a02c2d934b6182ac9e68df387900d55aea182cb7d0c7bf6035f5d2 | 3f4a0d64bf09050966e4d8460e04088119f0c5af483bc862484ff07ecabfc118 | O=C1NC(=O)c2ccccc21 | Br-[CH;D3;+0:1](-[CH3;D1;+0:2])-[CH;D3;+0:3](-[Br;D1;H0:4])-[CH3;D1;+0:5].[O;D1;H0:6]=[C:7]1-[NH;D2;+0:8]-[C:9](=[O;D1;H0:10])-[c:11]:[c:12]-1>>[Br;D1;H0:4]-[CH2;D2;+0:3]-[CH2;D2;+0:1]-[CH2;D2;+0:2]-[CH2;D2;+0:5]-[N;H0;D3;+0:8]1-[C:9](=[O;D1;H0:10])-[c:11]:[c:12]-[C:7]-1=[O;D1;H0:6] | 58 | [{"value": 58.0, "product": "BrCCCCN1C(C2=CC=CC=C2C1=O)=O", "details": "PERCENTYIELD", "is_desired": false}] | 90 | CELSIUS | 5 | HOUR | To a hot solution (90° C.) of dibromobutane (1.50 kg, 6.95 mol) in dimethylformamide (1.7 L) was added potassium phthalimide (329 g, 1.74 mol). The solution was stirred at 90° C. for 5 hours. The solution was cooled to room temperature prior to the addition of water (900 mL). The layers were separated and the aqueous l... | 10.6084/m9.figshare.5104873.v1 | null | Secondary halide.Secondary halide.Unsubstituted dicarboximide | Primary halide.Substituted dicarboximide | c1ccc2c(c1)CNC2 | c1ccc2c(c1)C[NH]C2 | c1ccc2c(c1)C[NH]C2 | HBr | null | 90 | 5 | CC(Br)C(C)Br.O=C1NC(=O)c2ccccc21>>O=C1c2ccccc2C(=O)N1CCCCBr |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-16d3ff05724c49799b5dd239f1f80e7f | Cc1cccnc1C1CC(=O)CC(c2ncccc2C)N1>>Cc1cccnc1C1CCCC(c2ncccc2C)N1 | CC=1C(=NC=CC1)C1NC(CC(C1)=O)C1=NC=CC=C1C.O.NN.[OH-].[K+]>>CC=1C(=NC=CC1)C1NC(CCC1)C1=NC=CC=C1C | O=[C:10]1[CH2:9][CH:8]([c:7]2[c:2]([CH3:1])[cH:3][cH:4][cH:5][n:6]2)[NH:20][CH:12]([c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[CH3:19])[CH2:11]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][n:6][c:7]1[CH:8]1[CH2:9][CH2:10][CH2:11][CH:12]([c:13]2[n:14][cH:15][cH:16][cH:17][c:18]2[CH3:19])[NH:20]1 | Cc1cccnc1C1CC(=O)CC(c2ncccc2C)N1 | Cc1cccnc1C1CCCC(c2ncccc2C)N1 | null | null | C(COCCO)O | Reduction | OtherReaction | 480c86d699cecfc77c66c4f0456bd74413c6252cfa33cc10192db180010e8392 | f9ba67182f94acd5fbe41487f8f71e26bccf898b8fc8091ef46f4363de5628d4 | c1ccc(C2CCCC(c3ccccn3)N2)nc1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1>>[#7:4]1-[C:3]-[C:2]-[CH2;D2;+0:1]-[C:6]-[C:5]-1 | 97 | [{"value": 97.0, "product": "CC=1C(=NC=CC1)C1NC(CCC1)C1=NC=CC=C1C", "details": "PERCENTYIELD", "is_desired": false}, {"value": 96.7, "product": "CC=1C(=NC=CC1)C1NC(CCC1)C1=NC=CC=C1C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 125 | CELSIUS | 2 | HOUR | To a solution of 3,3″-dimethyl-2′,3′,5′,6′-tetrahydro-1′H-[2,2′;6′,2″]terpyridin-4′-one (9.6 g, 34.1 mmol) in diethylene glycol (170 mL) was added hydrazine monohydrate (90 mL, 2.89 mol) and potassium hydroxide pellets (57.4 g, 1.02 mol) and the reaction stirred at 125° C. for 2 hours. 50 mL of hydrazine distilled off ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | null | C1CCNCC1 | C1CCNCC1 | c1ccncc1.C1CCNCC1.c1ccncc1 | Other | C(COCCO)O | 125 | 2 | Cc1cccnc1C1CC(=O)CC(c2ncccc2C)N1>C(COCCO)O>Cc1cccnc1C1CCCC(c2ncccc2C)N1 |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-4a15a491c355436d97368bb672ec079a | COC(=O)[C@@H](N)Cc1ccc(-c2ccccc2)cc1.Nc1ccc(Br)cc1C(=O)O>>COC(=O)[C@H](Cc1ccc(-c2ccccc2)cc1)NC(=O)c1cc(Br)ccc1N | COC([C@H](CC1=CC=C(C=C1)C1=CC=CC=C1)N)=O.BrC=1C=CC(=C(C(=O)O)C1)N>>COC([C@H](CC1=CC=C(C=C1)C1=CC=CC=C1)NC(C1=C(C=CC(=C1)Br)N)=O)=O | [CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1)[NH2:19].O[C:20](=[O:21])[c:22]1[cH:23][c:24]([Br:25])[cH:26][cH:27][c:28]1[NH2:29]>>[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2... | COC(=O)[C@@H](N)Cc1ccc(-c2ccccc2)cc1.Nc1ccc(Br)cc1C(=O)O | COC(=O)[C@H](Cc1ccc(-c2ccccc2)cc1)NC(=O)c1cc(Br)ccc1N | null | null | null | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(NCCc1ccc(-c2ccccc2)cc1)c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7](-[NH2;D1;+0:8])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12]>>[C:6]-[C:7](-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5])-[C:9](=[O;D1;H0:10])-[#8:11]-[C;D1;H3:12] | 82.3 | [{"value": 80.0, "product": "COC([C@H](CC1=CC=C(C=C1)C1=CC=CC=C1)NC(C1=C(C=CC(=C1)Br)N)=O)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 82.3, "product": "COC([C@H](CC1=CC=C(C=C1)C1=CC=CC=C1)NC(C1=C(C=CC(=C1)Br)N)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | (2S)-(2-amino-5-bromo-benzoyl-amino)-3-biphenyl-4-yl-propionic acid methyl ester (1.53 g, 80%) was prepared from (2S)-amino-3-biphenyl-4-yl-propionic acid methyl ester (1.0 g, 4.1 mmol) and 5-bromo-2-amino-benzoic acid (1.23 g, 4.9 mmol) as described in procedure A.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | HO- | null | null | null | COC(=O)[C@@H](N)Cc1ccc(-c2ccccc2)cc1.Nc1ccc(Br)cc1C(=O)O>>COC(=O)[C@H](Cc1ccc(-c2ccccc2)cc1)NC(=O)c1cc(Br)ccc1N |
ord_dataset-c31cb9b44c404c10ba3aa533aa079e2b | ord-ab00b5f3e45e4be3a73101d5ff61a76e | CC(C)(C)c1ccc(S(=O)(=O)Cl)cc1.COC(=O)[C@H](Cc1ccc(-c2ccccc2)cc1)NC(=O)c1cc(Br)ccc1N>>COC(=O)C(Cc1ccc(-c2ccccc2)cc1)NC(=O)c1cc(Br)ccc1NS(=O)(=O)c1ccc(C(C)(C)C)cc1 | COC([C@H](CC1=CC=C(C=C1)C1=CC=CC=C1)NC(C1=C(C=CC(=C1)Br)N)=O)=O.N1=CC=CC=C1.C(C)(C)(C)C1=CC=C(C=C1)S(=O)(=O)Cl>>COC(C(CC1=CC=C(C=C1)C1=CC=CC=C1)NC(C1=C(C=CC(=C1)Br)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)=O)=O | Cl[S:30](=[O:31])(=[O:32])[c:33]1[cH:34][cH:35][c:36]([C:37]([CH3:38])([CH3:39])[CH3:40])[cH:41][cH:42]1.[CH3:1][O:2][C:3](=[O:4])[C@H:5]([CH2:6][c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1)[NH:19][C:20](=[O:21])[c:22]1[cH:23][c:24]([Br:25])[cH:26][cH:27][c:28]1[NH2:29]>>[CH3:1]... | CC(C)(C)c1ccc(S(=O)(=O)Cl)cc1.COC(=O)[C@H](Cc1ccc(-c2ccccc2)cc1)NC(=O)c1cc(Br)ccc1N | COC(=O)C(Cc1ccc(-c2ccccc2)cc1)NC(=O)c1cc(Br)ccc1NS(=O)(=O)c1ccc(C(C)(C)C)cc1 | null | null | C(Cl)Cl | Acylation | Sulfonamide synthesis (Schotten-Baumann) primary amine | 4c44ef6d7646f6ef25dd125d2c32c713d8dcae7c603407faa5f0fb810631670e | 8fce8115d8a725afa92eb3910ded29d4c852e5133eba78a425054f41f7142603 | O=C(NCCc1ccc(-c2ccccc2)cc1)c1ccccc1NS(=O)(=O)c1ccccc1 | Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[NH2;D1;+0:12]):[c:13]>>[#7:7]-[C:8](=[O;D1;H0:9])-[c:10]:[c:11](-[NH;D2;+0:12]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]):[c:13] | 96.2 | [{"value": 96.2, "product": "COC(C(CC1=CC=C(C=C1)C1=CC=CC=C1)NC(C1=C(C=CC(=C1)Br)NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a stirring solution of (2S)-(2-amino-5-bromo-benzoyl-amino)-3-biphenyl-4-yl-propionic acid methyl ester (1.0 g, 2 mmol) prepared above dissolved in DCM containing pyridine (1.58 g, 4 mmol), was added 4-tert-butylbenzenesulfonyl chloride (1.20 g, 2.5 mmol) at 0° C. The reaction mixture was stirred at rt for 3 h, extr... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine.Sulfonyl halide | Sulfonamide | null | null | c1ccccc1.c1ccccc1.c1ccccc1.c1ccccc1 | HCl | C(Cl)Cl | null | 3 | CC(C)(C)c1ccc(S(=O)(=O)Cl)cc1.COC(=O)[C@H](Cc1ccc(-c2ccccc2)cc1)NC(=O)c1cc(Br)ccc1N>C(Cl)Cl>COC(=O)C(Cc1ccc(-c2ccccc2)cc1)NC(=O)c1cc(Br)ccc1NS(=O)(=O)c1ccc(C(C)(C)C)cc1 |
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