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-c3a75813d0b24864aa4f7cd526efd6aa | ord-909429328f9c43f0b3f4f7598de5461c | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(NC(=O)OC(C)(C)C)C(=O)OC)cc1>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(N)C(=O)OC)cc1 | C(C)(C)(C)OC(=O)NC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=NOC)=O.C(=O)(C(F)(F)F)O>>NC(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=NOC)=O | CC(C)(C)OC(=O)[NH:30][CH:29]([CH2:28][c:27]1[cH:26][cH:25][c:24]([O:23][CH2:22][CH2:21][n:20]2[c:14]3[cH:13][cH:12][c:11]([C:4](=[N:3][O:2][CH3:1])[c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[cH:16][c:15]3[s:17][c:18]2=[O:19])[cH:36][cH:35]1)[C:31](=[O:32])[O:33][CH3:34]>>[CH3:1][O:2][N:3]=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:... | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(NC(=O)OC(C)(C)C)C(=O)OC)cc1 | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(N)C(=O)OC)cc1 | null | null | C(Cl)Cl | Reduction | Hydrogenolysis of amides/imides/carbamates | 3c33dd2a2d355ee5ba0287367e209aa147a39aa00607f0c95fb2bf1ade45d014 | c5b5dffe7dd8beebdc1baa8b5b05300a9f7079e65dcfd42ade6f8a77ff09537d | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | C-C(-C)(-C)-O-C(=O)-[NH;D2;+0:1]-[C:2](-[C:3])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7]>>[C:3]-[C:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[#8:6]-[C;D1;H3:7] | null | [] | null | null | 5 | HOUR | Dissolve the compound obtained in Example 10 (1 eq.) in 250 ml of anhydrous DCM and add TFA (20 eq.) dropwise. Stir for 5 hours and evaporate. Take up in water and render alkaline using 10% K2CO3. Extract with ethyl acetate. Wash the organic phases with water, dry over MgSO4, filter and evaporate. Take up in a minimum ... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Primary amine | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HO- | C(Cl)Cl | null | 5 | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(NC(=O)OC(C)(C)C)C(=O)OC)cc1>C(Cl)Cl>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(N)C(=O)OC)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-860dedf2fc534956b98b8e133ac89c91 | CI.COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)OC(C)(C)C>>COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)N(C)C(=O)OC(C)(C)C | Cl.C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)NC(=O)OC(C)(C)C)C=C1.CI.[H-].[Na+]>>C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)N(C)C(=O)OC(C)(C)C)C=C1 | I[CH3:35].[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH2:6][c:7]1[cH:8][cH:9][c:10]([O:11][CH2:12][CH2:13][n:14]2[c:15](=[O:16])[s:17][c:18]3[cH:19][c:20]([C:21](=[O:22])[c:23]4[cH:24][cH:25][cH:26][cH:27][cH:28]4)[cH:29][cH:30][c:31]23)[cH:32][cH:33]1)[NH:34][C:36](=[O:37])[O:38][C:39]([CH3:40])([CH3:41])[CH3:42]>>[CH3:1][O:2][... | CI.COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)OC(C)(C)C | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)N(C)C(=O)OC(C)(C)C | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 29c841ae076cb6ee785aad2a4e3ce1a9b47357d7ad25657b8d9991b1347f5721 | c485eddcb40c5a0d396ffdb624041effa09ee4f5ca2ecce3fe13077cf65004ed | O=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | I-[CH3;D1;+0:1].[C:2]-[C:3](-[NH;D2;+0:4]-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3:11])-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15]>>[C:2]-[C:3](-[C:12](=[O;D1;H0:13])-[#8:14]-[C;D1;H3:15])-[N;H0;D3;+0:4](-[CH3;D1;+0:1])-[C:5](=[O;D1;H0:6])-[#8:7]-[C:8](-[C;D1;H3:9])(-[C;D1;H3:10])-[C;D1;H3... | null | [] | null | null | null | null | Dissolve the compound obtained in Step C of Example 10 (1 eq.) and CH3I (2 eq.): in 55 ml of anhydrous DMF and place in an ice bath at 0° C. Add NaH (1.5 eq.) in portions. Allow to return to ambient temperature. Hydrolyse, acidify with 1N HCl and filter. Purify the resulting crude product by chromatography on silica ge... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester | Carbamic ester | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HI | CN(C)C=O | null | null | CI.COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)NC(=O)OC(C)(C)C>CN(C)C=O>COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)N(C)C(=O)OC(C)(C)C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-708b24f2e5e34bcf94303c04d4f13d44 | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)N(C)C(=O)OC(C)(C)C.CON>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(C(=O)OC)N(C)C(=O)OC(C)(C)C)cc1 | C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)N(C)C(=O)OC(C)(C)C)C=C1.CON>>C(C)(C)(C)OC(=O)N(C(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=NOC)=O)C | O=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[s:17][c:18](=[O:19])[n:20]2[CH2:21][CH2:22][O:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][CH:29]([C:30](=[O:31])[O:32][CH3:33])[N:34]([CH3:35])[C:36](=[O:37])[O:38][C:39]([CH3:40])([CH3:41])[CH3:42])[cH:43][cH:44]1.[CH3:1][O:2][NH2:... | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)N(C)C(=O)OC(C)(C)C.CON | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(C(=O)OC)N(C)C(=O)OC(C)(C)C)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C;D1;H3:10]-[#8:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[#8:11]-[C;D1;H3:10])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | Starting from the compound obtained in Step A, the procedure is as in Step B of Example 2, replacing the hydroxylamine by O-methylhydroxylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HO- | null | null | null | COC(=O)C(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)N(C)C(=O)OC(C)(C)C.CON>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(C(=O)OC)N(C)C(=O)OC(C)(C)C)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-11eebd30777b45dc9263fedb0c3509d0 | CON.O=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC2C(=O)Oc3ccccc32)cc1>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC2C(=O)Oc3ccccc32)cc1 | C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC2C(OC3=C2C=CC=C3)=O)C=C1.CON>>CON=C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC2C(OC3=C2C=CC=C3)=O)C=C1)C1=CC=CC=C1 | [CH3:1][O:2][NH2:3].O=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[s:17][c:18](=[O:19])[n:20]2[CH2:21][CH2:22][O:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][CH:29]2[C:30](=[O:31])[O:32][c:33]3[cH:34][cH:35][cH:36][cH:37][c:38]32)[cH:39][cH:40]1>>[CH3:1][O:2][N:3]=[C:4]([c:5]1[cH... | CON.O=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC2C(=O)Oc3ccccc32)cc1 | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC2C(=O)Oc3ccccc32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC2C(=O)Oc3ccccc32)cc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C;D1;H3:10]-[#8:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[#8:11]-[C;D1;H3:10])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | Starting from the compound obtained in Step A, the procedure is as in Step B of Example 2, replacing the hydroxylamine by O-methylhydroxylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1.c1ccc2c(c1)CCO2 | HO- | null | null | null | CON.O=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC2C(=O)Oc3ccccc32)cc1>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC2C(=O)Oc3ccccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c1cef0531c944d71b832c83ba61f51c7 | CO.CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC2C(=O)Oc3ccccc32)cc1>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(C(=O)OC)c2ccccc2O)cc1 | CON=C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC2C(OC3=C2C=CC=C3)=O)C=C1)C1=CC=CC=C1.CO>>OC1=C(C=CC=C1)C(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=NOC)=O | [OH:32][CH3:33].[CH3:1][O:2][N:3]=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[s:17][c:18](=[O:19])[n:20]2[CH2:21][CH2:22][O:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][CH:29]2[C:30](=[O:31])[O:40][c:39]3[c:34]2[cH:35][cH:36][cH:37][cH:38]3)[cH:41][cH:42]1>>[CH3:1][O:2][N:3]=[C:... | CO.CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC2C(=O)Oc3ccccc32)cc1 | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(C(=O)OC)c2ccccc2O)cc1 | null | null | S(O)(O)(=O)=O | Protection | OtherReaction | 6cfd4d1df6f9006d5687793df661d40f989ff8374937b623a149a85c7a294a6a | 5e4632d88056171b71c6999a966b3ed8f4e96271d8ecc461eaaa15cb46640ba7 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CCc2ccccc2)cc1 | [C;D1;H3:1]-[OH;D1;+0:2].[C:3]-[C:4]1-[c:5]:[c:6](:[c:7])-[O;H0;D2;+0:8]-[C;H0;D3;+0:9]-1=[O;D1;H0:10]>>[C:3]-[C:4](-[c:5]:[c:6](-[OH;D1;+0:8]):[c:7])-[C;H0;D3;+0:9](=[O;D1;H0:10])-[O;H0;D2;+0:2]-[C;D1;H3:1] | null | [] | null | null | null | null | 1.5 g of the compound obtained in Step B, in 50 ml of methanol and 0.1 ml of concentrated sulphuric acid, are heated at reflux for 2 hours. The solvent is then evaporated off, the residue is hydrolysed and the precipitate obtained is chromatographed on silica gel (eluant: AcOEt/toluene 5/95).
Conditions: See reaction.n... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Methanol | Ester.Aromatic alcohol | c1ccc2c(c1)CCO2 | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1.c1ccccc1 | null | S(O)(O)(=O)=O | null | null | CO.CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC2C(=O)Oc3ccccc32)cc1>S(O)(O)(=O)=O>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(C(=O)OC)c2ccccc2O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-79a3ed52a681452f9e6408051ec6d478 | COC(=O)C(Cc1ccccc1)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.CON>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(Cc2ccccc2)C(=O)OC)cc1 | C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(CC(C(=O)OC)CC3=CC=CC=C3)C=C2)C=C1.CON>>C(C1=CC=CC=C1)C(C(=O)OC)CC1=CC=C(C=C1)OCCN1C(SC2=C1C=CC(=C2)C(C2=CC=CC=C2)=NOC)=O | O=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[s:17][c:18](=[O:19])[n:20]2[CH2:21][CH2:22][O:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][CH:29]([CH2:30][c:31]2[cH:32][cH:33][cH:34][cH:35][cH:36]2)[C:37](=[O:38])[O:39][CH3:40])[cH:41][cH:42]1.[CH3:1][O:2][NH2:3]>>[CH3:1][O:2][N:3... | COC(=O)C(Cc1ccccc1)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.CON | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(Cc2ccccc2)C(=O)OC)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CCCc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C;D1;H3:10]-[#8:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[#8:11]-[C;D1;H3:10])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | Starting from the compound obtained in Step A, the procedure is as in Step B of Example 2, replacing the hydroxylamine by O-methylhydroxylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1.c1ccccc1 | HO- | null | null | null | COC(=O)C(Cc1ccccc1)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.CON>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(Cc2ccccc2)C(=O)OC)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b3e19273d94248e8a46697073c36fcfe | COC(=O)C(CCc1ccccc1)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.CON>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(CCc2ccccc2)C(=O)OC)cc1 | C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(CC(C(=O)OC)CCC3=CC=CC=C3)C=C2)C=C1.CON>>CON=C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(CC(C(=O)OC)CCC3=CC=CC=C3)C=C2)C=C1)C1=CC=CC=C1 | O=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[s:17][c:18](=[O:19])[n:20]2[CH2:21][CH2:22][O:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][CH:29]([CH2:30][CH2:31][c:32]2[cH:33][cH:34][cH:35][cH:36][cH:37]2)[C:38](=[O:39])[O:40][CH3:41])[cH:42][cH:43]1.[CH3:1][O:2][NH2:3]>>[CH3:1][... | COC(=O)C(CCc1ccccc1)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.CON | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(CCc2ccccc2)C(=O)OC)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CCCCc2ccccc2)cc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C;D1;H3:10]-[#8:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[#8:11]-[C;D1;H3:10])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | Starting from the compound obtained in Step A, the procedure is as in Step B of Example 2, replacing the hydroxylamine by O-methylhydroxylamine. The two (Z) and (E) compounds are not separated.
Conditions: See reaction.notes.procedure_details.
Workup: The two (Z) and (E) compounds are not separated | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1.c1ccccc1 | HO- | null | null | null | COC(=O)C(CCc1ccccc1)Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.CON>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(CCc2ccccc2)C(=O)OC)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-eee1c52aaa5b4766814cbe2cf60d8cf5 | CCOC(=O)C(C)(C)Oc1ccc(OCCCl)cc1.O=C(c1ccccc1)c1ccc2c(c1)S(=O)C=N2>>CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1 | [OH-].[Na+].C(C1=CC=CC=C1)(=O)C1=CC2=C(N=CS2=O)C=C1.C(=O)([O-])[O-].[K+].[K+].ClCCOC1=CC=C(OC(C(=O)OCC)(C)C)C=C1>>C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)OCC)(C)C)C=C2)C=C1 | Cl[CH2:16][CH2:15][O:14][c:13]1[cH:12][cH:11][c:10]([O:9][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8])[cH:36][cH:35]1.[N:17]1=[CH:18][S:20](=[O:19])[c:21]2[cH:22][c:23]([C:24](=[O:25])[c:26]3[cH:27][cH:28][cH:29][cH:30][cH:31]3)[cH:32][cH:33][c:34]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[O... | CCOC(=O)C(C)(C)Oc1ccc(OCCCl)cc1.O=C(c1ccccc1)c1ccc2c(c1)S(=O)C=N2 | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 42c83f048334b1ed148ed7afdbd743f45dba21a36b3061112c38545e7e60436d | 3dcb031a7507da808ae5e1b8f13ca2c4f0152648164857a941ec9d83076e2a56 | O=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[O;H0;D1;+0:4]=[S;H0;D3;+0:5]1-[CH;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]-1:[c:11]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:7]1:[c:8](:[c:9]):[c:10](:[c:11]):[s;H0;D2;+0:5]:[c;H0;D3;+0:6]:1=[O;H0;D1;+0:4] | null | [] | 120 | CELSIUS | null | null | To a solution, heated at 80° C. for 2 hours, of 6-benzoyl-benzothiazolinone (6.7 mmol) in the presence of K2CO3 in 20 ml of DMF there is added ethyl 2-[4-(2-chloroethoxy)phenoxy]-2-methylpropanoate. The reaction mixture is heated at 120° C. for 5 days, cooled, hydrolysed using 100 ml of water and rendered alkaline usin... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Sulfoxide | null | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HCl | O.CN(C)C=O | 120 | null | CCOC(=O)C(C)(C)Oc1ccc(OCCCl)cc1.O=C(c1ccccc1)c1ccc2c(c1)S(=O)C=N2>O.CN(C)C=O>CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b5f77654d99d40ec94ce5c7a18edac57 | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.CON>>CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1 | Cl.C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)OCC)(C)C)C=C2)C=C1.Cl.CON>>CON=C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)OCC)(C)C)C=C2)C=C1)C1=CC=CC=C1 | O=[C:24]([c:23]1[cH:22][c:21]2[s:20][c:18](=[O:19])[n:17]([CH2:16][CH2:15][O:14][c:13]3[cH:12][cH:11][c:10]([O:9][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8])[cH:38][cH:37]3)[c:36]2[cH:35][cH:34]1)[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1.[NH2:25][O:26][CH3:27]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7... | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.CON | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C;D1;H3:10]-[#8:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[#8:11]-[C;D1;H3:10])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | A solution of the compound obtained in Step A (500 mg) and O-methylhydroxylamine hydrochloride (165 mg) in 15 ml of pyridine is heated at reflux for 3 hours. The reaction mixture is hydrolysed using 100 ml of ice-cold water, acidified using 6N HCl and then extracted with ethyl acetate. The organic phase is dried over m... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HO- | N1=CC=CC=C1 | null | null | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.CON>N1=CC=CC=C1>CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f46bba6eaa754bbfac2c0e0b61e99bc0 | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.NO>>CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NO)c4ccccc4)ccc32)cc1 | Cl.C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)OCC)(C)C)C=C2)C=C1.Cl.NO>>ON=C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)OCC)(C)C)C=C2)C=C1)C1=CC=CC=C1 | O=[C:24]([c:23]1[cH:22][c:21]2[s:20][c:18](=[O:19])[n:17]([CH2:16][CH2:15][O:14][c:13]3[cH:12][cH:11][c:10]([O:9][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8])[cH:37][cH:36]3)[c:35]2[cH:34][cH:33]1)[c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1.[NH2:25][OH:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3... | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.NO | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NO)c4ccccc4)ccc32)cc1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | b5fd91d879f097d0ef2e8e2d3ef7d2ef0195968870a9602a47b8324c601790b9 | 1a0ef15294bdb221fb8888b5d4c7fcf00473b11e53da288791d32747daa48d23 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[NH2;D1;+0:10]-[O;D1;H1:11]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:10]-[O;D1;H1:11])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | A solution of the compound obtained in Step A of Example 31 (500 mg) and hydroxylamine hydrochloride (137 mg) in 10 ml of pyridine is heated at reflux for 3 hours. The reaction mixture is hydrolysed using 100 ml of ice-cold water and is acidified using 6N HCl. The precipitate obtained is then filtered off, washed with ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Oxime | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HO- | N1=CC=CC=C1 | null | null | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.NO>N1=CC=CC=C1>CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NO)c4ccccc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-264340a5610d49d1950476b864cc05dc | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1>>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(OC(C)(C)C(=O)O)cc1 | Cl.CON=C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)OCC)(C)C)C=C2)C=C1)C1=CC=CC=C1.[OH-].[K+]>>CON=C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)O)(C)C)C=C2)C=C1)C1=CC=CC=C1 | CC[O:34][C:32]([C:29]([O:28][c:27]1[cH:26][cH:25][c:24]([O:23][CH2:22][CH2:21][n:20]2[c:14]3[cH:13][cH:12][c:11]([C:4](=[N:3][O:2][CH3:1])[c:5]4[cH:6][cH:7][cH:8][cH:9][cH:10]4)[cH:16][c:15]3[s:17][c:18]2=[O:19])[cH:36][cH:35]1)([CH3:30])[CH3:31])=[O:33]>>[CH3:1][O:2][N:3]=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[... | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1 | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(OC(C)(C)C(=O)O)cc1 | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | To a solution of the compound obtained in Step B of Example 31 (0.8 g) in 5 ml of ethanol 95° there is added potassium hydroxide (100 mg) dissolved in 1 ml of ethanol 95° The reaction mixture is heated at reflux overnight. After cooling to ambient temperature, the solution is acidified using 1N HCl. The precipitate obt... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | Other | C(C)O | null | null | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1>C(C)O>CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(OC(C)(C)C(=O)O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5476e58a4d654c8d9d6fe2c2dbb09b99 | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NO)c4ccccc4)ccc32)cc1>>CC(C)(Oc1ccc(OCCn2c(=O)sc3cc(C(=NO)c4ccccc4)ccc32)cc1)C(=O)O | Cl.ON=C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)OCC)(C)C)C=C2)C=C1)C1=CC=CC=C1.[OH-].[K+]>>ON=C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)O)(C)C)C=C2)C=C1)C1=CC=CC=C1 | CC[O:35][C:33]([C:2]([CH3:1])([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][n:12]2[c:13](=[O:14])[s:15][c:16]3[cH:17][c:18]([C:19](=[N:20][OH:21])[c:22]4[cH:23][cH:24][cH:25][cH:26][cH:27]4)[cH:28][cH:29][c:30]23)[cH:31][cH:32]1)=[O:34]>>[CH3:1][C:2]([CH3:3])([O:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:... | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NO)c4ccccc4)ccc32)cc1 | CC(C)(Oc1ccc(OCCn2c(=O)sc3cc(C(=NO)c4ccccc4)ccc32)cc1)C(=O)O | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | To a solution of the compound obtained in Example 32 (0.5 g) in 5 ml of ethanol 95° there is added potassium hydroxide (107 mg) dissolved in 1 ml of ethanol 95°. The reaction mixture is heated at reflux overnight. After cooling to ambient temperature, the solution is acidified using 1N HCl. The precipitate obtained is ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | Other | C(C)O | null | null | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NO)c4ccccc4)ccc32)cc1>C(C)O>CC(C)(Oc1ccc(OCCn2c(=O)sc3cc(C(=NO)c4ccccc4)ccc32)cc1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-82f2de4777404c1f83fd80eb7ede4828 | CCOC(=O)C(C)(C)Oc1ccc(OCCCl)cc1.O=C(c1cccc(Cl)c1)c1ccc2c(c1)S(=O)C=N2>>CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4cccc(Cl)c4)ccc32)cc1 | [OH-].[Na+].ClC=1C=C(C(=O)C2=CC3=C(N=CS3=O)C=C2)C=CC1.C(=O)([O-])[O-].[K+].[K+].ClCCOC1=CC=C(OC(C(=O)OCC)(C)C)C=C1>>ClC=1C=C(C(=O)C2=CC3=C(N(C(S3)=O)CCOC3=CC=C(OC(C(=O)OCC)(C)C)C=C3)C=C2)C=CC1 | Cl[CH2:16][CH2:15][O:14][c:13]1[cH:12][cH:11][c:10]([O:9][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8])[cH:37][cH:36]1.[N:17]1=[CH:18][S:20](=[O:19])[c:21]2[cH:22][c:23]([C:24](=[O:25])[c:26]3[cH:27][cH:28][cH:29][c:30]([Cl:31])[cH:32]3)[cH:33][cH:34][c:35]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([C... | CCOC(=O)C(C)(C)Oc1ccc(OCCCl)cc1.O=C(c1cccc(Cl)c1)c1ccc2c(c1)S(=O)C=N2 | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4cccc(Cl)c4)ccc32)cc1 | null | null | O.CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 42c83f048334b1ed148ed7afdbd743f45dba21a36b3061112c38545e7e60436d | 3dcb031a7507da808ae5e1b8f13ca2c4f0152648164857a941ec9d83076e2a56 | O=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[O;H0;D1;+0:4]=[S;H0;D3;+0:5]1-[CH;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]-1:[c:11]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:7]1:[c:8](:[c:9]):[c:10](:[c:11]):[s;H0;D2;+0:5]:[c;H0;D3;+0:6]:1=[O;H0;D1;+0:4] | null | [] | 120 | CELSIUS | null | null | To a solution, heated at 80° C. for 2 hours, of 6-(3′-chlorobenzoyl)-benzothiazolinone (1.8 g) in the presence of K2CO3 (1.72 g) in 20 ml of DMF there is added ethyl 2-[4-(2-chloroethoxy)phenoxy]-2-methylpropanoate (1.96 g). The reaction mixture is heated at 120° C. for 5 days, cooled, hydrolysed using 100 ml of water ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Sulfoxide | null | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HCl | O.CN(C)C=O | 120 | null | CCOC(=O)C(C)(C)Oc1ccc(OCCCl)cc1.O=C(c1cccc(Cl)c1)c1ccc2c(c1)S(=O)C=N2>O.CN(C)C=O>CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4cccc(Cl)c4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-43e233c2fe6e4d73b14262eec7767f6c | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4cccc(Cl)c4)ccc32)cc1.CON>>CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4cccc(Cl)c4)ccc32)cc1 | Cl.ClC=1C=C(C(=O)C2=CC3=C(N(C(S3)=O)CCOC3=CC=C(OC(C(=O)OCC)(C)C)C=C3)C=C2)C=CC1.Cl.CON>>ClC=1C=C(C=CC1)C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)OCC)(C)C)C=C2)C=C1)=NOC | O=[C:24]([c:23]1[cH:22][c:21]2[s:20][c:18](=[O:19])[n:17]([CH2:16][CH2:15][O:14][c:13]3[cH:12][cH:11][c:10]([O:9][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8])[cH:39][cH:38]3)[c:37]2[cH:36][cH:35]1)[c:28]1[cH:29][cH:30][cH:31][c:32]([Cl:33])[cH:34]1.[NH2:25][O:26][CH3:27]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6... | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4cccc(Cl)c4)ccc32)cc1.CON | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4cccc(Cl)c4)ccc32)cc1 | null | null | N1=CC=CC=C1 | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C;D1;H3:10]-[#8:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[#8:11]-[C;D1;H3:10])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | A solution of the compound obtained in Step A (1.00 g) and O-methylhydroxylamine hydrochloride (309 mg) in 15 ml of pyridine is heated at reflux for 3 hours. The reaction mixture is hydrolysed using 100 ml of ice-cold water and acidified using 6N HCl. The precipitate obtained is filtered off, washed with water and then... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HO- | N1=CC=CC=C1 | null | null | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4cccc(Cl)c4)ccc32)cc1.CON>N1=CC=CC=C1>CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4cccc(Cl)c4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b14af2bb85a04671a97996f852d4bdb4 | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NO)c4cccc(Cl)c4)ccc32)cc1>>CC(C)(Oc1ccc(OCCn2c(=O)sc3cc(C(=NO)c4cccc(Cl)c4)ccc32)cc1)C(=O)O | Cl.ClC=1C=C(C=CC1)C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)OCC)(C)C)C=C2)C=C1)=NO.[OH-].[K+]>>ClC=1C=C(C=CC1)C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)O)(C)C)C=C2)C=C1)=NO | CC[O:36][C:34]([C:2]([CH3:1])([CH3:3])[O:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:10][CH2:11][n:12]2[c:13](=[O:14])[s:15][c:16]3[cH:17][c:18]([C:19](=[N:20][OH:21])[c:22]4[cH:23][cH:24][cH:25][c:26]([Cl:27])[cH:28]4)[cH:29][cH:30][c:31]23)[cH:32][cH:33]1)=[O:35]>>[CH3:1][C:2]([CH3:3])([O:4][c:5]1[cH:6][cH:7][c:8]([O:9][CH2:... | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NO)c4cccc(Cl)c4)ccc32)cc1 | CC(C)(Oc1ccc(OCCn2c(=O)sc3cc(C(=NO)c4cccc(Cl)c4)ccc32)cc1)C(=O)O | null | null | C(C)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | To a solution of the compound obtained in Example 37 (0.6 g) in 5 ml of ethanol 95° there is added potassium hydroxide (90 mg) dissolved in 1 ml of ethanol 95°. The reaction mixture is heated at reflux overnight. After cooling to ambient temperature, the solution is acidified using 1N HCl. The precipitate obtained is t... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | Other | C(C)O | null | null | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NO)c4cccc(Cl)c4)ccc32)cc1>C(C)O>CC(C)(Oc1ccc(OCCn2c(=O)sc3cc(C(=NO)c4cccc(Cl)c4)ccc32)cc1)C(=O)O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a075e7720b934c6fb85c6f4b2e0ba3cb | CCOC(=O)C(C)(C)CCCOc1ccc(OCCCl)cc1.O=C(c1ccccc1)c1ccc2c(c1)S(=O)C=N2>>CCOC(=O)C(C)(C)CCCOc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1 | O.C(C1=CC=CC=C1)(=O)C1=CC2=C(N=CS2=O)C=C1.C(=O)([O-])[O-].[K+].[K+].ClCCOC1=CC=C(OCCCC(C(=O)OCC)(C)C)C=C1>>C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OCCCC(C(=O)OCC)(C)C)C=C2)C=C1 | Cl[CH2:19][CH2:18][O:17][c:16]1[cH:15][cH:14][c:13]([O:12][CH2:11][CH2:10][CH2:9][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8])[cH:39][cH:38]1.[N:20]1=[CH:21][S:23](=[O:22])[c:24]2[cH:25][c:26]([C:27](=[O:28])[c:29]3[cH:30][cH:31][cH:32][cH:33][cH:34]3)[cH:35][cH:36][c:37]21>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[... | CCOC(=O)C(C)(C)CCCOc1ccc(OCCCl)cc1.O=C(c1ccccc1)c1ccc2c(c1)S(=O)C=N2 | CCOC(=O)C(C)(C)CCCOc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1 | null | null | CN(C)C=O | Heteroatom Alkylation and Arylation | OtherReaction | 42c83f048334b1ed148ed7afdbd743f45dba21a36b3061112c38545e7e60436d | 3dcb031a7507da808ae5e1b8f13ca2c4f0152648164857a941ec9d83076e2a56 | O=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | Cl-[CH2;D2;+0:1]-[C:2]-[#8:3].[O;H0;D1;+0:4]=[S;H0;D3;+0:5]1-[CH;D2;+0:6]=[N;H0;D2;+0:7]-[c:8](:[c:9]):[c:10]-1:[c:11]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:7]1:[c:8](:[c:9]):[c:10](:[c:11]):[s;H0;D2;+0:5]:[c;H0;D3;+0:6]:1=[O;H0;D1;+0:4] | null | [] | 120 | CELSIUS | null | null | To a solution, heated at 80° C. for 2 hours, of 6-benzoyl-benzothiazolinone (1 g) in the presence of K2CO3 (1.08 g) in 10 ml of DMF there is added ethyl 5-[4-(2-chloroethoxy)phenoxy]-2,2-dimethylpentanoate (1.41 g). The reaction mixture is heated at 120° C. for 5 days and is then hydrolysed using 100 ml of water. The s... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Sulfoxide | null | c1ccc2scnc2c1 | c1ccc2scnc2c1 | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HCl | CN(C)C=O | 120 | null | CCOC(=O)C(C)(C)CCCOc1ccc(OCCCl)cc1.O=C(c1ccccc1)c1ccc2c(c1)S(=O)C=N2>CN(C)C=O>CCOC(=O)C(C)(C)CCCOc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-52ded71733214fc18f24b59c99b12ca7 | CCOC(=O)C(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.CON>>CCOC(=O)C(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1 | C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)OCC)C)C=C2)C=C1.CON>>CON=C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)OCC)C)C=C2)C=C1)C1=CC=CC=C1 | O=[C:23]([c:22]1[cH:21][c:20]2[s:19][c:17](=[O:18])[n:16]([CH2:15][CH2:14][O:13][c:12]3[cH:11][cH:10][c:9]([O:8][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH3:7])[cH:37][cH:36]3)[c:35]2[cH:34][cH:33]1)[c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1.[NH2:24][O:25][CH3:26]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH3:7])[O:8][... | CCOC(=O)C(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.CON | CCOC(=O)C(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C;D1;H3:10]-[#8:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[#8:11]-[C;D1;H3:10])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | Starting from the compound obtained in Step A, the procedure is as in Step B of Example 2, replacing the hydroxylamine by O-methylhydroxylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HO- | null | null | null | CCOC(=O)C(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.CON>>CCOC(=O)C(C)Oc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8abf8f58a68546f390b521c3721265a9 | CCOC(=O)C(CC)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.CON>>CCOC(=O)C(CC)Oc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1 | C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)OCC)CC)C=C2)C=C1.CON>>CON=C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)OCC)CC)C=C2)C=C1)C1=CC=CC=C1 | O=[C:24]([c:23]1[cH:22][c:21]2[s:20][c:18](=[O:19])[n:17]([CH2:16][CH2:15][O:14][c:13]3[cH:12][cH:11][c:10]([O:9][CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH3:8])[cH:38][cH:37]3)[c:36]2[cH:35][cH:34]1)[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1.[NH2:25][O:26][CH3:27]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]([CH2:7... | CCOC(=O)C(CC)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.CON | CCOC(=O)C(CC)Oc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C;D1;H3:10]-[#8:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[#8:11]-[C;D1;H3:10])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | Starting from the compound obtained in Step A, the procedure is as in Step B of Example 2, replacing the hydroxylamine by O-methylhydroxylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HO- | null | null | null | CCOC(=O)C(CC)Oc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1.CON>>CCOC(=O)C(CC)Oc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4ccccc4)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-26fc786b3d5346d4a077959ef5fcb4b9 | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(C)=O)ccc32)cc1.CON>>CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(C)=NOC)ccc32)cc1 | C(C)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)OCC)(C)C)C=C2)C=C1.CON>>CON=C(C)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(OC(C(=O)OCC)(C)C)C=C2)C=C1 | O=[C:24]([c:23]1[cH:22][c:21]2[s:20][c:18](=[O:19])[n:17]([CH2:16][CH2:15][O:14][c:13]3[cH:12][cH:11][c:10]([O:9][C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])([CH3:7])[CH3:8])[cH:33][cH:32]3)[c:31]2[cH:30][cH:29]1)[CH3:25].[NH2:26][O:27][CH3:28]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]([CH3:7])([CH3:8])[O:9][c:10]1[cH:11][cH:1... | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(C)=O)ccc32)cc1.CON | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(C)=NOC)ccc32)cc1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | O=c1sc2ccccc2n1CCOc1ccccc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[c:3](:[c:4]):[c:5]:[c:6]:[#16;a:7].[C;D1;H3:8]-[#8:9]-[NH2;D1;+0:10]>>[#16;a:7]:[c:6]:[c:5]:[c:3](-[C;H0;D3;+0:1](-[C;D1;H3:2])=[N;H0;D2;+0:10]-[#8:9]-[C;D1;H3:8]):[c:4] | null | [] | null | null | null | null | Starting from the compound obtained in Step A, the procedure is as in Step B of Example 2, replacing the hydroxylamine by O-methylhydroxylamine. The two (Z) and (E) compounds are not separated.
Conditions: See reaction.notes.procedure_details.
Workup: The two (Z) and (E) compounds are not separated | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1 | HO- | null | null | null | CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(C)=O)ccc32)cc1.CON>>CCOC(=O)C(C)(C)Oc1ccc(OCCn2c(=O)sc3cc(C(C)=NOC)ccc32)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8806e84ee0fb48c0ae41a84d9c3dcbae | CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4cccc(Cl)c4)ccc32)cc1)C(=O)OC.CON>>CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4cccc(Cl)c4)ccc32)cc1)C(=O)OC | ClC=1C=C(C(=O)C2=CC3=C(N(C(S3)=O)CCOC3=CC=C(C=C3)CC(C(=O)OC)OCC)C=C2)C=CC1.CON>>ClC=1C=C(C=CC1)C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)OCC)C=C1)=NOC | O=[C:20]([c:19]1[cH:18][c:17]2[s:16][c:14](=[O:15])[n:13]([CH2:12][CH2:11][O:10][c:9]3[cH:8][cH:7][c:6]([CH2:5][CH:4]([O:3][CH2:2][CH3:1])[C:36](=[O:37])[O:38][CH3:39])[cH:35][cH:34]3)[c:33]2[cH:32][cH:31]1)[c:24]1[cH:25][cH:26][cH:27][c:28]([Cl:29])[cH:30]1.[NH2:21][O:22][CH3:23]>>[CH3:1][CH2:2][O:3][CH:4]([CH2:5][c:6... | CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4cccc(Cl)c4)ccc32)cc1)C(=O)OC.CON | CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4cccc(Cl)c4)ccc32)cc1)C(=O)OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C;D1;H3:10]-[#8:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[#8:11]-[C;D1;H3:10])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | Starting from the compound obtained in Step A, the procedure is as in Step B of Example 2, replacing the hydroxylamine by O-methylhydroxylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HO- | null | null | null | CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4cccc(Cl)c4)ccc32)cc1)C(=O)OC.CON>>CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=NOC)c4cccc(Cl)c4)ccc32)cc1)C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e7d06a53b0af464291e716e56b46128e | CC(C)(C)ON.CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC>>CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=NOC(C)(C)C)c4ccccc4)ccc32)cc1)C(=O)OC | C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)OCC)C=C1.C(C)(C)(C)ON>>C(C)(C)(C)ON=C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)OCC)C=C1)C1=CC=CC=C1 | [NH2:21][O:22][C:23]([CH3:24])([CH3:25])[CH3:26].O=[C:20]([c:19]1[cH:18][c:17]2[s:16][c:14](=[O:15])[n:13]([CH2:12][CH2:11][O:10][c:9]3[cH:8][cH:7][c:6]([CH2:5][CH:4]([O:3][CH2:2][CH3:1])[C:38](=[O:39])[O:40][CH3:41])[cH:37][cH:36]3)[c:35]2[cH:34][cH:33]1)[c:27]1[cH:28][cH:29][cH:30][cH:31][cH:32]1>>[CH3:1][CH2:2][O:3]... | CC(C)(C)ON.CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC | CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=NOC(C)(C)C)c4ccccc4)ccc32)cc1)C(=O)OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C;D1;H3:10]-[C:11](-[C;D1;H3:12])(-[C;D1;H3:13])-[#8:14]-[NH2;D1;+0:15]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:15]-[#8:14]-[C:11](-[C;D1;H3:10])(-[C;D1;H3:12])-[C;D1;H3:13])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | Starting from the compound obtained in Step C of Example 1, the procedure is as in Step B of Example 2, replacing the hydroxylamine by O-(tert-butyl)hydroxylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | HO- | null | null | null | CC(C)(C)ON.CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC>>CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=NOC(C)(C)C)c4ccccc4)ccc32)cc1)C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e2c294d2b5db404aa07425636a9c1607 | CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC.NOCc1ccccc1>>CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=NOCc4ccccc4)c4ccccc4)ccc32)cc1)C(=O)OC | C(C1=CC=CC=C1)(=O)C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)OCC)C=C1.C(C1=CC=CC=C1)ON>>C(C1=CC=CC=C1)ON=C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)OC)OCC)C=C1)C1=CC=CC=C1 | O=[C:20]([c:19]1[cH:18][c:17]2[s:16][c:14](=[O:15])[n:13]([CH2:12][CH2:11][O:10][c:9]3[cH:8][cH:7][c:6]([CH2:5][CH:4]([O:3][CH2:2][CH3:1])[C:41](=[O:42])[O:43][CH3:44])[cH:40][cH:39]3)[c:38]2[cH:37][cH:36]1)[c:30]1[cH:31][cH:32][cH:33][cH:34][cH:35]1.[NH2:21][O:22][CH2:23][c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>>[C... | CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC.NOCc1ccccc1 | CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=NOCc4ccccc4)c4ccccc4)ccc32)cc1)C(=O)OC | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3d7a74a3d1c5abb5292963d4a3067f1fb8a89aead752dc9bb1d63522c4c0bd5c | 6b0edeaa66853687109d0d530554f76edf36b01a8ec084e7ae9c709f0949a6b9 | O=c1sc2cc(C(=NOCc3ccccc3)c3ccccc3)ccc2n1CCOc1ccccc1 | O=[C;H0;D3;+0:1](-[c:2](:[c:3]):[c:4]:[c:5]:[#16;a:6])-[c:7](:[c:8]):[c:9].[C:10]-[#8:11]-[NH2;D1;+0:12]>>[#16;a:6]:[c:5]:[c:4]:[c:2](-[C;H0;D3;+0:1](=[N;H0;D2;+0:12]-[#8:11]-[C:10])-[c:7](:[c:8]):[c:9]):[c:3] | null | [] | null | null | null | null | Starting from the compound obtained in Step C of Example 1, the procedure is as in Step B of Example 2, replacing the hydroxylamine by O-benzylhydroxylamine.
Conditions: See reaction.notes.procedure_details. | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1.c1ccccc1 | HO- | null | null | null | CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=O)c4ccccc4)ccc32)cc1)C(=O)OC.NOCc1ccccc1>>CCOC(Cc1ccc(OCCn2c(=O)sc3cc(C(=NOCc4ccccc4)c4ccccc4)ccc32)cc1)C(=O)OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-19b7ee442f184e3aac6214417427587e | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(OCC(F)(F)F)C(=O)O)cc1>>CO/N=C(/c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(OCC(F)(F)F)C(=O)O)cc1 | CON=C(C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)O)OCC(F)(F)F)C=C1)C1=CC=CC=C1>>CO\N=C(/C1=CC2=C(N(C(S2)=O)CCOC2=CC=C(C=C2)CC(C(=O)O)OCC(F)(F)F)C=C1)\C1=CC=CC=C1 | [CH3:1][O:2][N:3]=[C:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]2[c:15]([cH:16]1)[s:17][c:18](=[O:19])[n:20]2[CH2:21][CH2:22][O:23][c:24]1[cH:25][cH:26][c:27]([CH2:28][CH:29]([O:30][CH2:31][C:32]([F:33])([F:34])[F:35])[C:36](=[O:37])[OH:38])[cH:39][cH:40]1>>[CH3:1][O:2]/[N:3]=[C:4](/[c:5]1[cH:... | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(OCC(F)(F)F)C(=O)O)cc1 | CO/N=C(/c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(OCC(F)(F)F)C(=O)O)cc1 | null | null | C(C)OCC | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | N=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccccc1 | null | null | [] | null | null | null | null | The compound obtained in Example 62 is taken up in the diethyl ether. The filtrate is recovered and evaporated to yield the title compound.
Conditions: See reaction.notes.procedure_details.
Workup: The filtrate is recovered; evaporated | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccc2scnc2c1.c1ccccc1 | null | C(C)OCC | null | null | CON=C(c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(OCC(F)(F)F)C(=O)O)cc1>C(C)OCC>CO/N=C(/c1ccccc1)c1ccc2c(c1)sc(=O)n2CCOc1ccc(CC(OCC(F)(F)F)C(=O)O)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c4fb685667cc4027a9ae52d41dc084f1 | CO.Nc1ccc(Cl)c(C(=O)O)c1>>COC(=O)c1cc(N)ccc1Cl | NC=1C=CC(=C(C(=O)O)C1)Cl.S(O)(O)(=O)=O.CO>>COC(C1=C(C=CC(=C1)N)Cl)=O | [CH3:1][OH:2].O[C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:9][cH:10][c:11]1[Cl:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:9][cH:10][c:11]1[Cl:12] | CO.Nc1ccc(Cl)c(C(=O)O)c1 | COC(=O)c1cc(N)ccc1Cl | 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] | null | [] | null | null | null | null | To a slurry of 5-amino-2-chloro-benzoic acid (20.0 g, 0.12 mol) in methanol (150 mL) was added concentrated sulfuric acid (25 mL). The resulting reaction was heated at reflux for 4 hours, cooled, and concentrated in vacuo. The residual was taken up in water and neutralized with Na2CO3. The aqueous was extracted with CH... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Methanol | Ester | null | null | c1ccccc1 | HO- | null | null | null | CO.Nc1ccc(Cl)c(C(=O)O)c1>>COC(=O)c1cc(N)ccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6da8632a0fd04031988c99538c46b5f4 | COC(=O)c1cc(N)ccc1Cl>>COC(=O)c1cc(NN)ccc1Cl.Cl | COC(C1=C(C=CC(=C1)N)Cl)=O.O.O.Cl[Sn]Cl.C(C)(=O)O.N(=O)[O-].[Na+]>>Cl.COC(C1=C(C=CC(=C1)NN)Cl)=O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH2:8])[cH:10][cH:11][c:12]1[Cl:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][NH2:9])[cH:10][cH:11][c:12]1[Cl:13].[ClH:14] | COC(=O)c1cc(N)ccc1Cl | COC(=O)c1cc(NN)ccc1Cl.Cl | null | null | Cl.O | Miscellaneous | OtherReaction | c4079cd46dafde13b56adeac363106820ab4184dee8b1ca632594de2bba804bd | 5c8e4e590249a630a16b10bd7a77b27600fffbea367a0b585a920dd877e5471b | c1ccccc1 | [NH2;D1;+0:1]-[c:2](:[c:3]):[c:4]>>[N;D1;H2:5]-[NH;D2;+0:1]-[c:2](:[c:3]):[c:4] | 183.3 | [{"value": 183.3, "product": "Cl.COC(C1=C(C=CC(=C1)NN)Cl)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 15 | MINUTE | To 5-amino-2-chloro-benzoic acid methyl ester (14.0 g, 75.0 mmol) in water (100 mL) was added concentrated HCl (100 mL), followed by glacial acetic acid (100 mL). The solution was stirred at ambient temperature for 15 minutes. The reaction was then cooled to 0° C., and a solution of sodium nitrite (5.69, 82.5 mmol) in ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Hydrazine | null | null | c1ccccc1 | Other | Cl.O | null | 0.25 | COC(=O)c1cc(N)ccc1Cl>Cl.O>COC(=O)c1cc(NN)ccc1Cl.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a6440d65e9064d14ad3fc361a82b8d96 | COC(=O)c1cc(NN)ccc1Cl.O=CC(=O)O>>COC(=O)c1cc(NN=CC(=O)O)ccc1Cl | Cl.COC(C1=C(C=CC(=C1)NN)Cl)=O.O=CC(=O)O>>COC(C1=C(C=CC(=C1)NN=CC(=O)O)Cl)=O | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][NH2:9])[cH:14][cH:15][c:16]1[Cl:17].O=[CH:10][C:11](=[O:12])[OH:13]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([NH:8][N:9]=[CH:10][C:11](=[O:12])[OH:13])[cH:14][cH:15][c:16]1[Cl:17] | COC(=O)c1cc(NN)ccc1Cl.O=CC(=O)O | COC(=O)c1cc(NN=CC(=O)O)ccc1Cl | null | null | Cl | Heteroatom Alkylation and Arylation | OtherReaction | c78be09cf200f3a07b02946ce0bbc22b647e9aaae7494d0480373904a4f330a9 | c3cbc07b90655a7aa9777b584274a03a2ec0cff34c5b5edc214a16916fe29f1c | c1ccccc1 | O=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[O;D1;H1:4].[NH2;D1;+0:5]-[#7:6]-[c:7]>>[O;D1;H0:3]=[C:2](-[O;D1;H1:4])-[CH;D2;+0:1]=[N;H0;D2;+0:5]-[#7:6]-[c:7] | null | [] | null | null | 1.5 | HOUR | 2-Chloro-5-hydrazino-benzoic acid methyl ester hydrochloride salt (2.0 g, 8.5 mmol) and oxoacetic acid (1.0 g, 10 mmol) were taken up in 10% HCl and stirred at ambient temperature for 1.5 hours. The resulting orange precipitate was collected by filtration. The filter cake was taken up in EtOAc, washed with brine, and d... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Aldehyde | Hydrazone | null | null | c1ccccc1 | HO- | Cl | null | 1.5 | COC(=O)c1cc(NN)ccc1Cl.O=CC(=O)O>Cl>COC(=O)c1cc(NN=CC(=O)O)ccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-65a98d94232b4a8dbc1370dbf320c0ca | COC(=O)c1cc(-n2nc[nH]c2=O)ccc1Cl.NCC1(O)CCCCCC1>>O=C(NCC1(O)CCCCCC1)c1cc(-n2nc[nH]c2=O)ccc1Cl | COC(C1=C(C=CC(=C1)N1N=CNC1=O)Cl)=O.Cl.NCC1(CCCCCC1)O.C1=CN(C=N1)C(=O)N2C=CN=C2.C=1C=CC2=C(C1)N=NN2O>>ClC1=C(C(=O)NCC2(CCCCCC2)O)C=C(C=C1)N1N=CNC1=O | CO[C:2](=[O:1])[c:13]1[cH:14][c:15](-[n:16]2[n:17][cH:18][nH:19][c:20]2=[O:21])[cH:22][cH:23][c:24]1[Cl:25].[NH2:3][CH2:4][C:5]1([OH:6])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1>>[O:1]=[C:2]([NH:3][CH2:4][C:5]1([OH:6])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)[c:13]1[cH:14][c:15](-[n:16]2[n:17][cH:18][nH:19][... | COC(=O)c1cc(-n2nc[nH]c2=O)ccc1Cl.NCC1(O)CCCCCC1 | O=C(NCC1(O)CCCCCC1)c1cc(-n2nc[nH]c2=O)ccc1Cl | null | CN(C)C=1C=CN=CC1 | CN(C)C=O | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | O=C(NCC1CCCCCC1)c1cccc(-n2nc[nH]c2=O)c1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 3 | HOUR | To 2-chloro-5-(5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)-benzoic acid methyl ester (48.0 mg, 0.2 mmol) in DMF (3 mL) was added 1-aminomethyl-cycloheptanol HCl (54.0 mg, 0.3 mmol), polymer-supported CDI (660 mg, 0.6 mmol), polymer-supported DMAP (280 mg, 0.20 mmol), and HOBt (40.0 mg, 0.3 mmol). The resulting reaction was ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | C1CCCCCC1.c1ccccc1.c1nc[nH]n1 | HO- | CN(C)C=1C=CN=CC1.CN(C)C=O | null | 3 | COC(=O)c1cc(-n2nc[nH]c2=O)ccc1Cl.NCC1(O)CCCCCC1>CN(C)C=1C=CN=CC1.CN(C)C=O>O=C(NCC1(O)CCCCCC1)c1cc(-n2nc[nH]c2=O)ccc1Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d7b0d0dd863f4f7a88433015679f4e3f | COCCBr.O=C(NCC1(O)CCCCCC1)c1cc(-n2nc[nH]c2=O)ccc1Cl>>COCCn1cnn(-c2ccc(Cl)c(C(=O)NCC3(O)CCCCCC3)c2)c1=O | ClC1=C(C(=O)NCC2(CCCCCC2)O)C=C(C=C1)N1N=CNC1=O.C(=O)([O-])[O-].[Cs+].[Cs+].COCCBr>>ClC1=C(C(=O)NCC2(CCCCCC2)O)C=C(C=C1)N1N=CN(C1=O)CCOC | Br[CH2:4][CH2:3][O:2][CH3:1].[nH:5]1[cH:6][n:7][n:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[c:14]([C:15](=[O:16])[NH:17][CH2:18][C:19]3([OH:20])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)[cH:27]2)[c:28]1=[O:29]>>[CH3:1][O:2][CH2:3][CH2:4][n:5]1[cH:6][n:7][n:8](-[c:9]2[cH:10][cH:11][c:12]([Cl:13])[c:14]([C:15](=[O:... | COCCBr.O=C(NCC1(O)CCCCCC1)c1cc(-n2nc[nH]c2=O)ccc1Cl | COCCn1cnn(-c2ccc(Cl)c(C(=O)NCC3(O)CCCCCC3)c2)c1=O | null | null | O.CS(=O)C | Heteroatom Alkylation and Arylation | N-alkylation of secondary amines with alkyl halides | 8bef00eaa42d3c717b13b9e6e5eb0aaa548aa02b0e5b8a7323f70bc5d1c7c865 | 2e1e5fd9557b69cb528f6b2ffd179c67ef24ecb1a2c3994e1cdf0efe7ae19e9c | O=C(NCC1CCCCCC1)c1cccc(-n2nc[nH]c2=O)c1 | Br-[CH2;D2;+0:1]-[C:2]-[#8:3].[O;D1;H0:4]=[c:5]1:[nH;D2;+0:6]:[c:7]:[#7;a:8]:[#7;a:9]:1-[c:10]>>[#8:3]-[C:2]-[CH2;D2;+0:1]-[n;H0;D3;+0:6]1:[c:7]:[#7;a:8]:[#7;a:9](-[c:10]):[c:5]:1=[O;D1;H0:4] | 34.9 | [{"value": 34.9, "product": "ClC1=C(C(=O)NCC2(CCCCCC2)O)C=C(C=C1)N1N=CN(C1=O)CCOC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 48 | HOUR | A slurry of 2-Chloro-N-(1-hydroxy-cycloheptylmethyl)-5-(5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)-benzamide (44.4 mg, 0.122 mmol) and Cs2CO3 (66.0 mg, 0.202 mmol) were stirred in DMSO (0.813 mL) at ambient temperature for 20 minutes. 2-Bromoethyl methyl ether (17.0 mg, 0.122 mmol) was added and the reaction stirred at amb... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | null | c1nnc[nH]1 | c1nnc[nH]1 | c1nnc[nH]1.c1ccccc1.C1CCCCCC1 | HBr | O.CS(=O)C | null | 48 | COCCBr.O=C(NCC1(O)CCCCCC1)c1cc(-n2nc[nH]c2=O)ccc1Cl>O.CS(=O)C>COCCn1cnn(-c2ccc(Cl)c(C(=O)NCC3(O)CCCCCC3)c2)c1=O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6261267f2f8e4379be277cdae9ecfd82 | N#CC(c1ccccc1)(c1ccccc1)[C@@H]1CCN(Cc2ccccc2)C1>>N#CC(c1ccccc1)(c1ccccc1)[C@@H]1CCN(Cc2ccccc2)C1 | C(C1=CC=CC=C1)N1C[C@@H](CC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C#N.Cl>>Cl.C(C1=CC=CC=C1)N1C[C@@H](CC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C#N | [N:2]#[C:3][C: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)[C@@H:17]1[CH2:18][CH2:19][N:20]([CH2:21][c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[CH2:28]1>>[N:2]#[C:3][C: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)[C@@H:17]1[CH2:18][CH2... | N#CC(c1ccccc1)(c1ccccc1)[C@@H]1CCN(Cc2ccccc2)C1 | N#CC(c1ccccc1)(c1ccccc1)[C@@H]1CCN(Cc2ccccc2)C1 | null | null | null | Miscellaneous | OtherReaction | 40ba59785861b8226ce5af6bdcbb9a37f0ff50a8c7ec7d4fc4c524cf906cc65c | 56ebed4a8b3cebec83c37a71d68f0c87d1e404ab05a9ce792691e4e18a2379dd | c1ccc(CN2CC[C@@H](C(c3ccccc3)c3ccccc3)C2)cc1 | null | null | [] | null | null | null | null | (S)-1-Benzyl-3-(1-cyano-1,1-diphenylmethyl)pyrrolidine was dissolved in IPAc (approximately 1 g/10 mL) and the solution was mixed with an equal volume of 1N aqueous HCl. The resulting layers were separated and the aqueous layer was extracted with an equal volume of IPAc. The organic layers were combined, dried over sod... | 10.6084/m9.figshare.5104873.v1 | null | null | null | null | null | c1ccccc1.c1ccccc1.C1CC[NH]C1.c1ccccc1 | null | null | null | null | N#CC(c1ccccc1)(c1ccccc1)[C@@H]1CCN(Cc2ccccc2)C1>>N#CC(c1ccccc1)(c1ccccc1)[C@@H]1CCN(Cc2ccccc2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b8801616301c4e96a73b970a3e9c4467 | N#CC(c1ccccc1)(c1ccccc1)[C@@H]1CCN(Cc2ccccc2)C1>>N#CC(c1ccccc1)(c1ccccc1)[C@@H]1CCNC1 | Cl.C(C1=CC=CC=C1)N1C[C@@H](CC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C#N.C(=O)[O-].[NH4+].O>>C(#N)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@H]1CNCC1 | c1ccc(C[N:19]2[CH2:18][CH2:17][C@@H:16]([C:3]([C:2]#[N:1])([c:4]3[cH:5][cH:6][cH:7][cH:8][cH:9]3)[c:10]3[cH:11][cH:12][cH:13][cH:14][cH:15]3)[CH2:20]2)cc1>>[N:1]#[C:2][C:3]([c:4]1[cH:5][cH:6][cH:7][cH:8][cH:9]1)([c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1)[C@@H:16]1[CH2:17][CH2:18][NH:19][CH2:20]1 | N#CC(c1ccccc1)(c1ccccc1)[C@@H]1CCN(Cc2ccccc2)C1 | N#CC(c1ccccc1)(c1ccccc1)[C@@H]1CCNC1 | null | [Pd] | CO | Deprotection | Hydrogenolysis of tertiary amines | 846a35f8c83fa58d2c714915319a8bc96745602a4dd9ac20dbad14bc1e16a470 | 1c99dd446c0bf4ae872cd8df8de34955be195747c234e9f3c49f46d1de614f66 | c1ccc(C(c2ccccc2)[C@@H]2CCNC2)cc1 | C(-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[C:4]-[C:5]-1)-c1:c:c:c:c:c:1>>[C:4]1-[C:3]-[C:2]-[NH;D2;+0:1]-[C:5]-1 | 99.7 | [{"value": 99.7, "product": "C(#N)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@H]1CNCC1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 99.7, "product": "C(#N)C(C1=CC=CC=C1)(C1=CC=CC=C1)[C@H]1CNCC1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 50 | CELSIUS | 3 | HOUR | To a stirred solution of (S)-1-benzyl-3-(1-cyano-1,1-diphenylmethyl)-pyrrolidine hydrochloride (8.55 g, 21.98 mmol) in MeOH (44 mL) was added palladium on carbon (1.71 g) and ammonium formate (6.93 g, 109.9 mmol). The reaction mixture was heated to 50° C. with stirring for 3 hours. The reaction was cooled to ambient te... | 10.6084/m9.figshare.5104873.v1 | null | Tertiary amine | Secondary amine | c1ccccc1.C1CC[NH]C1 | C1CCNC1 | c1ccccc1.c1ccccc1.C1CCNC1 | Other | [Pd].CO | 50 | 3 | N#CC(c1ccccc1)(c1ccccc1)[C@@H]1CCN(Cc2ccccc2)C1>[Pd].CO>N#CC(c1ccccc1)(c1ccccc1)[C@@H]1CCNC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-598b57d4432c433ab63bb311f3240ad0 | CN(CC(=O)NCCCCCN1CC[C@@H](C(C(N)=O)(c2ccccc2)c2ccccc2)C1)C(=O)OC(C)(C)C>>CNCC(=O)NCCCCCN1CC[C@@H](C(C(N)=O)(c2ccccc2)c2ccccc2)C1 | C(C)(C)(C)OC(N(C)CC(NCCCCCN1C[C@@H](CC1)C(C1=CC=CC=C1)(C1=CC=CC=C1)C(N)=O)=O)=O.Cl.C(=O)(C(F)(F)F)O>>CNCC(=O)NCCCCCN1C[C@@H](CC1)C(C(=O)N)(C1=CC=CC=C1)C1=CC=CC=C1 | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][C:4](=[O:5])[NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][C@@H:15]([C:16]([C:17]([NH2:18])=[O:19])([c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[CH2:32]1>>[CH3:1][NH:2][CH2:3][C:4](=[O:5])[NH:6][CH2:7][CH2:8][CH2:9][CH2:... | CN(CC(=O)NCCCCCN1CC[C@@H](C(C(N)=O)(c2ccccc2)c2ccccc2)C1)C(=O)OC(C)(C)C | CNCC(=O)NCCCCCN1CC[C@@H](C(C(N)=O)(c2ccccc2)c2ccccc2)C1 | null | null | O1CCOCC1.C(Cl)Cl | Reduction | Boc amine deprotection | bbda4640db5f48af4538caded12fdadd56eacd6d4e5f7aefe46282d665df167e | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(C(c2ccccc2)[C@@H]2CCNC2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C;D1;H3:2])-[C:3]-[C:4](=[O;D1;H0:5])-[#7:6]-[C:7]>>[C:7]-[#7:6]-[C:4](=[O;D1;H0:5])-[C:3]-[NH;D2;+0:1]-[C;D1;H3:2] | 91.7 | [{"value": 91.7, "product": "CNCC(=O)NCCCCCN1C[C@@H](CC1)C(C(=O)N)(C1=CC=CC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | To a stirred solution of ({5-[(S)-3-(carbamoyldiphenylmethyl)pyrrolidin-1-yl]pentylcarbamoyl}methyl)methylcarbamic acid tert-butyl ester (23.47 g, 43.7 mmol) in DCM (60 mL) was added 4 N HCl in dioxane (100 mL). The reaction mixture was stirred at room temperature for 2 hours and then concentrated to dryness. The resid... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | null | null | C1CC[NH]C1.c1ccccc1.c1ccccc1 | HO- | O1CCOCC1.C(Cl)Cl | null | 2 | CN(CC(=O)NCCCCCN1CC[C@@H](C(C(N)=O)(c2ccccc2)c2ccccc2)C1)C(=O)OC(C)(C)C>O1CCOCC1.C(Cl)Cl>CNCC(=O)NCCCCCN1CC[C@@H](C(C(N)=O)(c2ccccc2)c2ccccc2)C1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c5390d5a8a25467485038a2668f38edf | COc1ccc(OC)c2ccccc12>>COc1cc(C=O)c(OC)c2ccccc12 | O.COC1=CC=C(C2=CC=CC=C12)OC.COC(Cl)Cl>>COC1=C(C=C(C2=CC=CC=C12)OC)C=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:8]([O:9][CH3:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[c:8]([O:9][CH3:10])[c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12 | COc1ccc(OC)c2ccccc12 | COc1cc(C=O)c(OC)c2ccccc12 | null | null | ClCCl | Miscellaneous | OtherReaction | 67ced7cb99084202a37bff5e70c1f0d5ea491cac26940b361bc4195cc20b94d1 | 3cccf922e74135722ee21a46ad7578302a8603e1f71d6f2113cd42de4ba0cf73 | c1ccc2ccccc2c1 | [#8:1]-[c:2](:[c:3]):[cH;D2;+0:4]:[c:5]:[c:6]>>[#8:1]-[c:2](:[c:3]):[c;H0;D3;+0:4](-[C:7]=[O;D1;H0:8]):[c:5]:[c:6] | null | [] | null | null | 30 | MINUTE | To a solution of 1,4-dimethoxy-naphthalene (5 g, 26.6 mmol) in dichloromethane (100 mL) at 0° C. was added dichloromethyl methyl ether (3.66 g, 31.9 mmol) and stannic chloride (13.8 g, 53.1 mmol). The reaction mixture was stirred for 30 min at this temperature, allowed to warm to room temperature and stirred for an add... | 10.6084/m9.figshare.5104873.v1 | null | null | Aldehyde | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | Other | ClCCl | null | 0.5 | COc1ccc(OC)c2ccccc12>ClCCl>COc1cc(C=O)c(OC)c2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-376d69b127ad44a48115925c1173cab5 | CC[N+](=O)[O-].COc1cc(C=O)c(OC)c2ccccc12>>COc1cc(C=C(C)[N+](=O)[O-])c(OC)c2ccccc12 | COC1=C(C=C(C2=CC=CC=C12)OC)C=O.C(C)(=O)[O-].[NH4+].[N+](=O)([O-])CC>>COC1=C(C=C(C2=CC=CC=C12)OC)C=C(C)[N+](=O)[O-] | [CH2:7]([CH3:8])[N+:9](=[O:10])[O-:11].O=[CH:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:20]2[c:15]([c:12]1[O:13][CH3:14])[cH:16][cH:17][cH:18][cH:19]2>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[C:7]([CH3:8])[N+:9](=[O:10])[O-:11])[c:12]([O:13][CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12 | CC[N+](=O)[O-].COc1cc(C=O)c(OC)c2ccccc12 | COc1cc(C=C(C)[N+](=O)[O-])c(OC)c2ccccc12 | null | null | null | C-C Coupling | OtherReaction | 7ede86d40d3d69f429dde089476c8b7ffa9b74bf3050590255e6323d013c2daf | f736727903c0ad5511d468246b8e380897fd19905174c118ffa4ed4d3651f6ea | c1ccc2ccccc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[CH2;D2;+0:6]-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9]>>[C;D1;H3:5]-[C;H0;D3;+0:6](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[#7;+:7](-[O;-;D1;H0:8])=[O;D1;H0:9] | null | [] | 60 | CELSIUS | 8 | HOUR | To a solution of the product from Step A (0.8 g, 2.93 mmol) in nitroethane (10 mL) was added ammonium acetate (0.45 g, 5.84 mmol). The mixture was stirred at 60° C. overnight. The excess nitroethane was removed and the residue purified by flash chromatography (silica gel, ethyl acetate/hexane: 0.5/9.5) to give 0.5 g of... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Enamine | null | null | c1ccc2ccccc2c1 | HO- | null | 60 | 8 | CC[N+](=O)[O-].COc1cc(C=O)c(OC)c2ccccc12>>COc1cc(C=C(C)[N+](=O)[O-])c(OC)c2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-a8b3689f37c24bc3bfcb44a80276c1aa | COc1cc(C=C(C)[N+](=O)[O-])c(OC)c2ccccc12>>COc1cc(CC(C)N)c(OC)c2ccccc12 | Cl.[H-].[Al+3].[Li+].[H-].[H-].[H-].COC1=C(C=C(C2=CC=CC=C12)OC)C=C(C)[N+](=O)[O-]>>Cl.COC1=C(C=C(C2=CC=CC=C12)OC)CC(C)N | O=[N+:9]([O-])[C:7](=[CH:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:18]2[c:13]([c:10]1[O:11][CH3:12])[cH:14][cH:15][cH:16][cH:17]2)[CH3:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][CH:7]([CH3:8])[NH2:9])[c:10]([O:11][CH3:12])[c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12 | COc1cc(C=C(C)[N+](=O)[O-])c(OC)c2ccccc12 | COc1cc(CC(C)N)c(OC)c2ccccc12 | null | null | O1CCCC1.C(C)OCC | Reduction | OtherReaction | 4337e4e8b75c4193a30be38c3139251eb50201a1e90dac1ecfc293dd3e226a46 | 1ad3bfd18d4cba7c52a6c2c4705cfa4e2dc99589d9555154a809489f21a7a436 | c1ccc2ccccc2c1 | O=[N+;H0;D3:1](-[O-])-[C;H0;D3;+0:2](-[C;D1;H3:3])=[CH;D2;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:3]-[CH;D3;+0:2](-[NH2;D1;+0:1])-[CH2;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | 0 | CELSIUS | null | null | The product from Step B (0.5 g, 1.83 mmol) was dissolved in tetrahydrofuran (50 mL). This solution was cooled to 0° C. and then a 1 M solution of lithium aluminum hydride in tetrahydrofuran (9 mL) was added. The reaction mixture was allowed to warm to room temperature and then warmed at reflux for an additional 5 h. Th... | 10.6084/m9.figshare.5104873.v1 | null | Enamine | Primary amine | null | null | c1ccc2ccccc2c1 | Other | O1CCCC1.C(C)OCC | 0 | null | COc1cc(C=C(C)[N+](=O)[O-])c(OC)c2ccccc12>O1CCCC1.C(C)OCC>COc1cc(CC(C)N)c(OC)c2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e7432b3077a04dd99c20e2dcc8995da1 | CCC(=O)Cl.COc1ccc(OC)c2ccccc12>>CCC(=O)c1cc(OC)c2ccccc2c1OC | O.[Cl-].[Al+3].[Cl-].[Cl-].COC1=CC=C(C2=CC=CC=C12)OC.C(CC)(=O)Cl>>COC1=C(C=C(C2=CC=CC=C12)OC)C(CC)=O | Cl[C:3]([CH2:2][CH3:1])=[O:4].[cH:5]1[cH:6][c:7]([O:8][CH3:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[c:16]1[O:17][CH3:18]>>[CH3:1][CH2:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([O:8][CH3:9])[c:10]2[cH:11][cH:12][cH:13][cH:14][c:15]2[c:16]1[O:17][CH3:18] | CCC(=O)Cl.COc1ccc(OC)c2ccccc12 | CCC(=O)c1cc(OC)c2ccccc2c1OC | null | null | ClC(C)Cl | C-C Coupling | Friedel-Crafts acylation | 12bfc1cb494a0014608d71eb38cabea029a6bf3a3526b0cc7babc0ad4f29f3e1 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | c1ccc2ccccc2c1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4].[#8:5]-[c:6](:[c:7]):[cH;D2;+0:8]:[c:9]:[c:10]>>[#8:5]-[c:6](:[c:7]):[c;H0;D3;+0:8](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;D1;H3:4]):[c:9]:[c:10] | 21.5 | [{"value": 21.5, "product": "COC1=C(C=C(C2=CC=CC=C12)OC)C(CC)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | To a cold solution (ice bath) of 1,4-dimethoxy-naphthalene (5 g, 26.6 mmol) in dichloroethane (100 mL) was added propionyl chloride (2.7 g, 29.3 mmol) followed by aluminum chloride (3.9 g, 29.3 mmol). After the addition was complete, the reaction mixture was allowed to warm to room temperature and stirred for 4 hr. Wat... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | HCl | ClC(C)Cl | null | 4 | CCC(=O)Cl.COc1ccc(OC)c2ccccc12>ClC(C)Cl>CCC(=O)c1cc(OC)c2ccccc2c1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6ac4fd3e3c5d4e6bace153926c2ac20d | CCC(=O)c1cc(OC)c2ccccc2c1OC.CCCCON=O>>COc1cc(C(=O)C(C)=NO)c(OC)c2ccccc12 | Cl.COC1=C(C=C(C2=CC=CC=C12)OC)C(CC)=O.Cl.N(=O)OCCCC.N(=O)OCCCC>>COC1=C(C=C(C2=CC=CC=C12)OC)C(C(C)=NO)=O | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH2:8][CH3:9])[c:12]([O:13][CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12.CCCCO[N:10]=[O:11]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[C:8]([CH3:9])=[N:10][OH:11])[c:12]([O:13][CH3:14])[c:15]2[cH:16][cH:17][cH:18][cH:19][c:20]12 | CCC(=O)c1cc(OC)c2ccccc2c1OC.CCCCON=O | COc1cc(C(=O)C(C)=NO)c(OC)c2ccccc12 | null | null | C(C)OCC | Heteroatom Alkylation and Arylation | OtherReaction | 977610bf44fbda1e0a23f5dd16db8b0cb303f37c36d5a67ff66ec243f6e1d15c | 31357763b1be60679a29f55afc8815d0b4a90e485d09aebc6e88f16eae688399 | c1ccc2ccccc2c1 | C-C-C-C-O-[N;H0;D2;+0:1]=[O;H0;D1;+0:2].[C;D1;H3:3]-[CH2;D2;+0:4]-[C:5](=[O;D1;H0:6])-[c:7]>>[C;D1;H3:3]-[C;H0;D3;+0:4](=[N;H0;D2;+0:1]-[OH;D1;+0:2])-[C:5](=[O;D1;H0:6])-[c:7] | 55.9 | [{"value": 55.9, "product": "COC1=C(C=C(C2=CC=CC=C12)OC)C(C(C)=NO)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 4 | HOUR | The product from Step A (1.28 g, 5.24 mmol) was dissolved in ethyl ether (50 mL), anhydrous hydrogen chloride gas was added through this solution at moderate rate for 5 min. Butyl nitrite (0.68 mL, 5.77 mmol) was then added dropwise. Hydrogen chloride bubbling was continued for an additional 10 min. after addition of b... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Nitroso | Ketone.Oxime | null | null | c1ccc2ccccc2c1 | HO- | C(C)OCC | null | 4 | CCC(=O)c1cc(OC)c2ccccc2c1OC.CCCCON=O>C(C)OCC>COc1cc(C(=O)C(C)=NO)c(OC)c2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-0893e4388b4946148f4fb6c36f0aa994 | COc1ccc(OC)c2ccccc12.C[C@@H](NC(=O)C(F)(F)F)C(=O)O>>COc1cc(C(=O)[C@@H](C)NC(=O)C(F)(F)F)c(OC)c2ccccc12 | FC(C(=O)N[C@H](C)C(=O)O)(F)F.[Al+3].[Cl-].[Cl-].[Cl-].COC1=CC=C(C2=CC=CC=C12)OC>>COC1=C(C=C(C2=CC=CC=C12)OC)C([C@@H](C)NC(C(F)(F)F)=O)=O | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:17]([O:18][CH3:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]12.O[C:6](=[O:7])[C@@H:8]([CH3:9])[NH:10][C:11](=[O:12])[C:13]([F:14])([F:15])[F:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[C@@H:8]([CH3:9])[NH:10][C:11](=[O:12])[C:13]([F:14])([F:15])[F:16])[c:17]([O:18][CH3:19])[c:20]2[... | COc1ccc(OC)c2ccccc12.C[C@@H](NC(=O)C(F)(F)F)C(=O)O | COc1cc(C(=O)[C@@H](C)NC(=O)C(F)(F)F)c(OC)c2ccccc12 | null | null | ClCCl.C(Cl)Cl | C-C Coupling | Friedel-Crafts acylation | 6c02866b83e7a20d3fad869afb283fb288a49d5d0ad15036a6cc97e1db12cdce | a49756d2995b35bf1c4b6840928f031562470ef5bd676447fb43ce2575147daa | c1ccc2ccccc2c1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7].[#8:8]-[c:9](:[c:10]):[cH;D2;+0:11]:[c:12]:[c:13]>>[#8:8]-[c:9](:[c:10]):[c;H0;D3;+0:11](-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](-[C;D1;H3:4])-[#7:5]-[C:6]=[O;D1;H0:7]):[c:12]:[c:13] | 32.6 | [{"value": 32.6, "product": "COC1=C(C=C(C2=CC=CC=C12)OC)C([C@@H](C)NC(C(F)(F)F)=O)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | To a suspension of AlCl3 (3.8 g, 28.6 mmol) in dichloromethane (100 mL) was added a solution of 1,4-dimethoxynaphthalene (4.88 g, 25.9 mmol) in dichloromethane (50 mL). To this mixture was added a solution of (R)-N-trifluoroacetylalanine (16 g, 86.5 mmol) in CH2Cl2 (50 mL); this mixture was stirred at room temperature ... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Ketone | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | HO- | ClCCl.C(Cl)Cl | null | 3 | COc1ccc(OC)c2ccccc12.C[C@@H](NC(=O)C(F)(F)F)C(=O)O>ClCCl.C(Cl)Cl>COc1cc(C(=O)[C@@H](C)NC(=O)C(F)(F)F)c(OC)c2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4d9520f5a9c04390ae86ba1ae95e1a5f | COS(=O)(=O)OC.O=C(O)c1ccc2ccccc2c1O>>COC(=O)c1ccc2ccccc2c1OC | S(=O)(=O)(OC)OC.OC1=C(C=CC2=CC=CC=C12)C(=O)O.C([O-])([O-])=O.[K+].[K+]>>COC1=C(C=CC2=CC=CC=C12)C(=O)OC | O=S(=O)(O[CH3:1])O[CH3:16].[OH:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[c:14]1[OH:15]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[c:14]1[O:15][CH3:16] | COS(=O)(=O)OC.O=C(O)c1ccc2ccccc2c1O | COC(=O)c1ccc2ccccc2c1OC | null | null | CC(=O)C.C(C)(=O)OCC | Heteroatom Alkylation and Arylation | OtherReaction | a73a0b4bed36565b493919c1511184d75109f6c557167d64c85b98af57b69588 | edd21dfad97802e784d20c5398257e85c9ec7c075392afa5ab3339d34ce0623f | c1ccc2ccccc2c1 | O=S(=O)(-O-[CH3;D1;+0:1])-O-[CH3;D1;+0:2].[O;D1;H0:3]=[C:4](-[OH;D1;+0:5])-[c:6]:[c:7](-[OH;D1;+0:8]):[c:9]>>[CH3;D1;+0:1]-[O;H0;D2;+0:8]-[c:7](:[c:9]):[c:6]-[C:4](=[O;D1;H0:3])-[O;H0;D2;+0:5]-[CH3;D1;+0:2] | 90.4 | [{"value": 90.4, "product": "COC1=C(C=CC2=CC=CC=C12)C(=O)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1-hydroxy-naphthalene-2-carboxylic acid (5 g, 26.6 mmol) in acetone (100 mL) was added potassium carbonate (11 g, 79.72 mmol) followed by dimethyl sulfate (7.38 g, 58.46 mmol). The reaction mixture was refluxed overnight and then diluted with ethyl acetate (200 mL) and washed with water. The organic la... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol | Ester.Ether | null | null | c1ccc2ccccc2c1 | HO- | CC(=O)C.C(C)(=O)OCC | null | null | COS(=O)(=O)OC.O=C(O)c1ccc2ccccc2c1O>CC(=O)C.C(C)(=O)OCC>COC(=O)c1ccc2ccccc2c1OC |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cd5c48fb49a04e97be2dc29a00d259d3 | COC(=O)c1ccc2ccccc2c1OC>>COc1c(CO)ccc2ccccc12 | C(C)(=O)OCC.[H-].[Al+3].[Li+].[H-].[H-].[H-].COC1=C(C=CC2=CC=CC=C12)C(=O)OC>>OCC1=C(C2=CC=CC=C2C=C1)OC | CO[C:5]([c:4]1[c:3]([O:2][CH3:1])[c:14]2[c:9]([cH:8][cH:7]1)[cH:10][cH:11][cH:12][cH:13]2)=[O:6]>>[CH3:1][O:2][c:3]1[c:4]([CH2:5][OH:6])[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12 | COC(=O)c1ccc2ccccc2c1OC | COc1c(CO)ccc2ccccc12 | null | null | O1CCCC1 | Reduction | Reduction of ester to primary alcohol | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccc2ccccc2c1 | 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] | 104.6 | [{"value": 104.6, "product": "OCC1=C(C2=CC=CC=C2C=C1)OC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 30 | MINUTE | The product of Step A (4.5 g, 20.83 mmol) was dissolved in anhydrous tetrahydrofuran (100 mL) and cooled to 0° C. To this solution was added a 1 M solution of lithium aluminum hydride in tetrahydrofuran (31 mL). The mixture was stirred at this temperature for 30 min, allowed to warm up to room temperature, and stirred ... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccc2ccccc2c1 | Other | O1CCCC1 | 0 | 0.5 | COC(=O)c1ccc2ccccc2c1OC>O1CCCC1>COc1c(CO)ccc2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c876af2d9b2c4dcc8051aa884d4c2ab1 | COc1c(CO)ccc2ccccc12>>COc1c(C=O)ccc2ccccc12 | OCC1=C(C2=CC=CC=C2C=C1)OC.[Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1>>COC1=C(C=CC2=CC=CC=C12)C=O | [CH3:1][O:2][c:3]1[c:4]([CH2:5][OH:6])[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12>>[CH3:1][O:2][c:3]1[c:4]([CH:5]=[O:6])[cH:7][cH:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]12 | COc1c(CO)ccc2ccccc12 | COc1c(C=O)ccc2ccccc12 | null | null | ClCCl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccc2ccccc2c1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | 0 | CELSIUS | 1 | HOUR | The product from Step B (4 g, 27.28 mmol) was dissolved in dichloromethane (100 mL) and cooled to 0° C. To this solution was added pyridinium chlorochromate (5.5 g, 25.53 mmol) and the reaction was stirred at this temperature for 1 h. The reaction mixture was washed with 1 M aqueous solution of hydrogen chloride. The o... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccc2ccccc2c1 | null | ClCCl | 0 | 1 | COc1c(CO)ccc2ccccc12>ClCCl>COc1c(C=O)ccc2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cfb43091512a41c38f51122a705bcdbd | CC[N+](=O)[O-].COc1c(C=O)ccc2ccccc12>>COc1c(CC(C)N)ccc2ccccc12 | [H-].[Al+3].[Li+].[H-].[H-].[H-].[N+](=O)([O-])CC.Cl.C(C)(=O)[O-].[NH4+].COC1=C(C=CC2=CC=CC=C12)C=O>>Cl.COC1=C(C=CC2=CC=CC=C12)CC(C)N | O=[N+:8]([O-])[CH2:6][CH3:7].O=[CH:5][c:4]1[c:3]([O:2][CH3:1])[c:16]2[c:11]([cH:10][cH:9]1)[cH:12][cH:13][cH:14][cH:15]2>>[CH3:1][O:2][c:3]1[c:4]([CH2:5][CH:6]([CH3:7])[NH2:8])[cH:9][cH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]12 | CC[N+](=O)[O-].COc1c(C=O)ccc2ccccc12 | COc1c(CC(C)N)ccc2ccccc12 | null | null | O1CCCC1.C(C)OCC.C(C)O | Functional Group Interconversion | OtherReaction | c4948e685a5307dbb0ab39cc775435d9f18bdf3d98a988199508e5c7eca2d454 | 31831dfce215791960c88ffc82ccac6c15baeee7c4c4ea60fee7e78d0106ef98 | c1ccc2ccccc2c1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].O=[N+;H0;D3:5](-[O-])-[CH2;D2;+0:6]-[C;D1;H3:7]>>[C;D1;H3:7]-[CH;D3;+0:6](-[NH2;D1;+0:5])-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | 70 | CELSIUS | 3 | HOUR | The product from Step C (3.04 g, 18.3 mmol) was dissolved in ethanol (50 mL), ammonium acetate (1.55 g, 20.10 mmol) was added followed by nitroethane (2.75 g, 36.5 mmol). The reaction mixture was stirred at 70° C. for 3 h and then the solvent was removed. The residue was dissolved in ethyl acetate (100 mL) and washed w... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitro group | Primary amine | null | null | c1ccc2ccccc2c1 | Other | O1CCCC1.C(C)OCC.C(C)O | 70 | 3 | CC[N+](=O)[O-].COc1c(C=O)ccc2ccccc12>O1CCCC1.C(C)OCC.C(C)O>COc1c(CC(C)N)ccc2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-322771b3977d4496a9db69836b0f773d | BrBr.COc1c(CC(C)N)ccc2ccccc12>>COc1c(CC(C)N)cc(Br)c2ccccc12 | BrBr.Cl.COC1=C(C=CC2=CC=CC=C12)CC(C)N.FC(C(=O)OC(C(F)(F)F)=O)(F)F>>Cl.BrC1=CC(=C(C2=CC=CC=C12)OC)CC(C)N | Br[Br:11].[CH3:1][O:2][c:3]1[c:4]([CH2:5][CH:6]([CH3:7])[NH2:8])[cH:9][cH:10][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[CH3:1][O:2][c:3]1[c:4]([CH2:5][CH:6]([CH3:7])[NH2:8])[cH:9][c:10]([Br:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12 | BrBr.COc1c(CC(C)N)ccc2ccccc12 | COc1c(CC(C)N)cc(Br)c2ccccc12 | null | null | ClCCl | Functional Group Interconversion | Bromination | 3f028b3cb6667dfa94ac17841fc3d30723adc1bece1338dfafcba1f81845cc2e | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ccccc2c1 | Br-[Br;H0;D1;+0:1].[c:2]:[c:3](:[c:4]):[cH;D2;+0:5]:[c:6]:[c:7]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:3](:[c:2]):[c:4] | null | [] | 0 | CELSIUS | 1 | HOUR | To a solution of the product from Example 4 (1.2 g, 4.78 mmol) and TEA (0.97 g, 9.56 mmol) in dichloromethane (100 ml) at 0° C. was added trifluoroacetic anhydride (1.2 g, 5.74 mmol). The reaction mixture was stirred at 0° C. for 1 h and evaporated to a residue, which was filtered through silica (ethyl acetate/hexane: ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | HBr | ClCCl | 0 | 1 | BrBr.COc1c(CC(C)N)ccc2ccccc12>ClCCl>COc1c(CC(C)N)cc(Br)c2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-cde8aa8f36f64caa85bf895d0748e51a | COc1c(CC(C)N)ccc2ccccc12>>CC(N)Cc1ccc2ccccc2c1O | Cl.COC1=C(C=CC2=CC=CC=C12)CC(C)N.Br>>Cl.OC1=C(C=CC2=CC=CC=C12)CC(C)N | C[O:15][c:14]1[c:5]([CH2:4][CH:2]([CH3:1])[NH2:3])[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]21>>[CH3:1][CH:2]([NH2:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]2[c:14]1[OH:15] | COc1c(CC(C)N)ccc2ccccc12 | CC(N)Cc1ccc2ccccc2c1O | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc2ccccc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A solution of 2-(1-methoxy-naphthalen-2-yl)-1-methylethylamine hydrochloride (0.1 g, 0.40 mmol) and HBr 48% was refluxed for 3 h. The reaction mixture was concentrated under vacuum, the residue was washed with hexane and ether and then collected by filtration: 1H NMR (DMSO-d) δ 1.14 (d, 3H, CH3), 2.86–3.11 (m, 2H, CH2)... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccc2ccccc2c1 | Other | null | null | null | COc1c(CC(C)N)ccc2ccccc12>>CC(N)Cc1ccc2ccccc2c1O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c8e7cb25be944baf86677b3c5e4b9408 | COc1cc(C(=O)C(C)=NO)c(OC)c2ccccc12>>COc1cc(C(=O)C(C)N)c(OC)c2ccccc12 | COC1=C(C=C(C2=CC=CC=C12)OC)C(C(C)=NO)=O.Cl.O>>Cl.NC(C(=O)C1=C(C2=CC=CC=C2C(=C1)OC)OC)C | O[N:10]=[C:8]([C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:19]2[c:14]([c:11]1[O:12][CH3:13])[cH:15][cH:16][cH:17][cH:18]2)=[O:7])[CH3:9]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH:8]([CH3:9])[NH2:10])[c:11]([O:12][CH3:13])[c:14]2[cH:15][cH:16][cH:17][cH:18][c:19]12 | COc1cc(C(=O)C(C)=NO)c(OC)c2ccccc12 | COc1cc(C(=O)C(C)N)c(OC)c2ccccc12 | null | [Pd] | C(C)O | Reduction | OtherReaction | b7ca3f61b8b30140990222f00a4d6af83c258b1760b11f7f7486b0f8e5478e46 | 178656017be156591ed8f29982ee3a5eb5737c28c6bf11051dfba481e2bb48a3 | c1ccc2ccccc2c1 | O-[N;H0;D2;+0:1]=[C;H0;D3;+0:2](-[C;D1;H3:3])-[C:4](=[O;D1;H0:5])-[c:6]>>[C;D1;H3:3]-[CH;D3;+0:2](-[NH2;D1;+0:1])-[C:4](=[O;D1;H0:5])-[c:6] | null | [] | null | null | 12 | HOUR | To a solution of 1-(1,4-dimethoxynaphthalen-2-yl)-propane-1,2-dione 2-oxime (1 g, 3.66 mmol, Example 2, Step B) in 1 M hydrogen chloride in ethanol (50 mL) was added Pd/C 10% (100 mg), The mixture was hydrogenated on a Parr hydrogenator apparatus under 40–50 psi pressure for 12 h. The catalyst was separated by filtrati... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Oxime | Ketone.Primary amine | null | null | c1ccc2ccccc2c1 | Other | [Pd].C(C)O | null | 12 | COc1cc(C(=O)C(C)=NO)c(OC)c2ccccc12>[Pd].C(C)O>COc1cc(C(=O)C(C)N)c(OC)c2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b7b56b27075a459bb5c8651b01ad1115 | BrBr.COc1cc(CC(C)N)cc2ccccc12>>COc1cc(CC(C)N)c(Br)c2ccccc12 | Cl.COC1=CC(=CC2=CC=CC=C12)CC(C)N.BrBr>>Cl.BrC1=C(C=C(C2=CC=CC=C12)OC)CC(C)N | Br[Br:11].[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][CH:7]([CH3:8])[NH2:9])[cH:10][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH2:6][CH:7]([CH3:8])[NH2:9])[c:10]([Br:11])[c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]12 | BrBr.COc1cc(CC(C)N)cc2ccccc12 | COc1cc(CC(C)N)c(Br)c2ccccc12 | null | null | ClCCl | Functional Group Interconversion | Bromination | 3f028b3cb6667dfa94ac17841fc3d30723adc1bece1338dfafcba1f81845cc2e | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc2ccccc2c1 | Br-[Br;H0;D1;+0:1].[C:2]-[c:3](:[c:4]):[cH;D2;+0:5]:[c:6](:[c:7]):[c:8]>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:5](:[c:6](:[c:7]):[c:8]):[c:3](-[C:2]):[c:4] | null | [] | null | null | null | null | To a cold heterogeneous solution (ice bath) of 2-(4-methoxy-naphthalen-2-yl) 1-methyl-ethylamine hydrochloride (0.10 g, 0.39 mmol, Example 11) in dichloromethane, was added bromine (0.07 g, 0.43 mmol) via syringe. After 1 h the volatiles were evaporated and the residue was partitioned in a mixture of ethyl acetate (20 ... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | c1ccc2ccccc2c1 | HBr | ClCCl | null | null | BrBr.COc1cc(CC(C)N)cc2ccccc12>ClCCl>COc1cc(CC(C)N)c(Br)c2ccccc12 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e6e98be830eb44eab480e0c3b34cfda2 | CCOC(=O)CBr.O=C(O)CN1CCC(n2c(=O)[nH]c3ccccc32)CC1>>CCOC(=O)CN1CCC(n2c(=O)[nH]c3ccccc32)CC1 | O=C1NC2=C(N1C1CCNCC1)C=CC=C2.O=C1NC2=C(N1C1CCN(CC1)CC(=O)O)C=CC=C2.BrCC(=O)OCC>>O=C1NC2=C(N1C1CCN(CC1)CC(=O)OCC)C=CC=C2 | Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].O=C(O)C[N:7]1[CH2:8][CH2:9][CH:10]([n:11]2[c:12](=[O:13])[nH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)[CH2:21][CH2:22]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N:7]1[CH2:8][CH2:9][CH:10]([n:11]2[c:12](=[O:13])[nH:14][c:15]3[cH:16][cH:17][cH:18][cH:19][c:20]23)[CH2:21][CH... | CCOC(=O)CBr.O=C(O)CN1CCC(n2c(=O)[nH]c3ccccc32)CC1 | CCOC(=O)CN1CCC(n2c(=O)[nH]c3ccccc32)CC1 | null | null | C(C)#N | Heteroatom Alkylation and Arylation | OtherReaction | 80f5b5bef34a91832522456384c894e84b326f4976f8c6bb6ccd1413fa87e3b1 | 5e49cf00bd17391fcb272cb481c9600e6c39e7c28c33721dcc37b5cb979c7ce1 | O=c1[nH]c2ccccc2n1C1CCNCC1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5].O-C(=O)-C-[N;H0;D3;+0:6](-[C:7]-[C:8])-[C:9]-[C:10]>>[C:8]-[C:7]-[N;H0;D3;+0:6](-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:9]-[C:10] | null | [] | null | null | null | null | Compounds of formula A in which Z=2,3-dihydro-2-oxo-1H-benzimidazol-1-yl and L=(N-methylene)piperidin-4-yl are prepared from β-aminotetralins (VII) or phenethylamines (XI) and [4-(2-keto-1-benzimidazolinyl)piperidin-1-yl]acetic acid (Schemes 6–7). For example, 4-(2-keto-1-benzimidazolinyl)piperidine is reacted with a b... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Carboxylic acid.Ester.Tertiary amine | Ester.Tertiary amine | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1.c1ccc2[nH]cnc2c1 | HBr | C(C)#N | null | null | CCOC(=O)CBr.O=C(O)CN1CCC(n2c(=O)[nH]c3ccccc32)CC1>C(C)#N>CCOC(=O)CN1CCC(n2c(=O)[nH]c3ccccc32)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-84481c84dce14da58451666086b906a5 | CCOC(=O)CN1CCC(n2c(=O)[nH]c3ccccc32)CC1>>O=C(O)CN1CCC(n2c(=O)[nH]c3ccccc32)CC1 | O=C1NC2=C(N1C1CCN(CC1)CC(=O)OCC)C=CC=C2.[OH-].[Na+].CO>>O=C1NC2=C(N1C1CCN(CC1)CC(=O)O)C=CC=C2 | CC[O:3][C:2](=[O:1])[CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([n:9]2[c:10](=[O:11])[nH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1>>[O:1]=[C:2]([OH:3])[CH2:4][N:5]1[CH2:6][CH2:7][CH:8]([n:9]2[c:10](=[O:11])[nH:12][c:13]3[cH:14][cH:15][cH:16][cH:17][c:18]23)[CH2:19][CH2:20]1 | CCOC(=O)CN1CCC(n2c(=O)[nH]c3ccccc32)CC1 | O=C(O)CN1CCC(n2c(=O)[nH]c3ccccc32)CC1 | null | null | C(C)(=O)O | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | O=c1[nH]c2ccccc2n1C1CCNCC1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | Compounds of formula A in which Z=2,3-dihydro-2-oxo-1H-benzimidazol-1-yl and L=(N-methylene)piperidin-4-yl are prepared from β-aminotetralins (VII) or phenethylamines (XI) and [4-(2-keto-1-benzimidazolinyl)piperidin-1-yl]acetic acid (Schemes 6–7). For example, 4-(2-keto-1-benzimidazolinyl)piperidine is reacted with a b... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC[NH]CC1.c1ccc2[nH]cnc2c1 | Other | C(C)(=O)O | null | null | CCOC(=O)CN1CCC(n2c(=O)[nH]c3ccccc32)CC1>C(C)(=O)O>O=C(O)CN1CCC(n2c(=O)[nH]c3ccccc32)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b50eeddfd0eb46a38835147e8be00222 | COc1ccc2c(c1)CC[C@H](NCCCCCCc1cc(N)cc(S(N)(=O)=O)c1F)[C@@H]2Cc1cccnc1.Cl>>Cl.Nc1cc(CCCCCCN[C@H]2CCc3cc(O)ccc3[C@H]2Cc2cccnc2)c(F)c(S(N)(=O)=O)c1 | B(Br)(Br)Br.Cl.Cl.Cl.NC=1C=C(C(=C(C1)S(=O)(=O)N)F)CCCCCCN[C@@H]1[C@@H](C2=CC=C(C=C2CC1)OC)CC=1C=NC=CC1>>Cl.Cl.Cl.NC=1C=C(C(=C(C1)S(=O)(=O)N)F)CCCCCCN[C@@H]1[C@@H](C2=CC=C(C=C2CC1)O)CC=1C=NC=CC1 | C[O:21][c:20]1[cH:19][c:18]2[c:24]([cH:23][cH:22]1)[C@@H:25]([CH2:26][c:27]1[cH:28][cH:29][cH:30][n:31][cH:32]1)[C@@H:15]([NH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][c:7]1[cH:6][c:5]([NH2:4])[cH:40][c:35]([S:36]([NH2:37])(=[O:38])=[O:39])[c:33]1[F:34])[CH2:16][CH2:17]2.[ClH:3]>>[ClH:3].[NH2:4][c:5]1[cH:6][c:7... | COc1ccc2c(c1)CC[C@H](NCCCCCCc1cc(N)cc(S(N)(=O)=O)c1F)[C@@H]2Cc1cccnc1.Cl | Cl.Nc1cc(CCCCCCN[C@H]2CCc3cc(O)ccc3[C@H]2Cc2cccnc2)c(F)c(S(N)(=O)=O)c1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 005318874c4792a3ed14897fb19099f1f6e548b285f476e19a15213a92356c2d | 0bab01685da92cdead9c84b3a9c513c0e9bd4114585991beae2460d8c47b3623 | c1ccc(CCCCCCN[C@H]2CCc3ccccc3[C@H]2Cc2cccnc2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 16 | HOUR | Aminotetralin sulfonamide 8 from the previous reaction (0.160 g, 0.246 mmol) was placed in a 50 mL round-bottom flask along with a stir bar. Methylene chloride (25 mL) was added and the slurry was cooled on an ice bath for several minutes. Boron tribromide in methylene chloride (1M, 1.25 mL, 1.25 mmol) was added to the... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2c(c1)CCCC2.c1ccncc1 | Other | C(Cl)Cl | null | 16 | COc1ccc2c(c1)CC[C@H](NCCCCCCc1cc(N)cc(S(N)(=O)=O)c1F)[C@@H]2Cc1cccnc1.Cl>C(Cl)Cl>Cl.Nc1cc(CCCCCCN[C@H]2CCc3cc(O)ccc3[C@H]2Cc2cccnc2)c(F)c(S(N)(=O)=O)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1bcba84b1cd54f95bde7c4d8a4ae878c | COc1ccc2c(c1)CCC(N)C2Cc1cccnc1.Cl.O=C(O)CN1CCC(n2c(=O)[nH]c3ccccc32)CC1>>COc1ccc2c(c1)CC[C@H](NC(=O)CN1CCC(n3c(=O)[nH]c4ccccc43)CC1)[C@@H]2Cc1cccnc1.Cl | F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)OC(=[N+](C)C)N(C)C.O=C1NC2=C(N1C1CCN(CC1)CC(=O)O)C=CC=C2.C(C)(C)N(C(C)C)CC.C([O-])(O)=O.[Na+].Cl.Cl.COC=1C=C2CCC(C(C2=CC1)CC=1C=NC=CC1)N>>Cl.Cl.O=C1NC2=C(N1C1CCN(CC1)CC(=O)N[C@@H]1[C@@H](C3=CC=C(C=C3CC1)OC)CC=1C=NC=CC1)C=CC=C2 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[CH2:9][CH2:10][CH:11]([NH2:12])[CH:32]2[CH2:33][c:34]1[cH:35][cH:36][cH:37][n:38][cH:39]1.[ClH:41].O[C:13](=[O:14])[CH2:15][N:16]1[CH2:17][CH2:18][CH:19]([n:20]2[c:21](=[O:22])[nH:23][c:24]3[cH:25][cH:26][cH:27][cH:28][c:29]23)[CH2:30][CH2:31]1>>[CH3:1][O:2][c:3]1[cH:4... | COc1ccc2c(c1)CCC(N)C2Cc1cccnc1.Cl.O=C(O)CN1CCC(n2c(=O)[nH]c3ccccc32)CC1 | COc1ccc2c(c1)CC[C@H](NC(=O)CN1CCC(n3c(=O)[nH]c4ccccc43)CC1)[C@@H]2Cc1cccnc1.Cl | null | null | CN(C=O)C | Acylation | OtherReaction | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | O=C(CN1CCC(n2c(=O)[nH]c3ccccc32)CC1)N[C@H]1CCc2ccccc2[C@H]1Cc1cccnc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[#7:4].[#7;a:5]:[c:6]:[c:7]-[C:8]-[CH;D3;+0:9]1-[CH;D3;+0:10](-[NH2;D1;+0:11])-[C:12]-[C:13]-[c:14]:[c:15]-1:[c:16]>>[#7:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:11]-[C@H;D3;+0:10]1-[C:12]-[C:13]-[c:14]:[c:15](:[c:16])-[C@H;D3;+0:9]-1-[C:8]-[c:7]:[c:6]:[#7;a:5] | 22 | [{"value": 22.0, "product": null, "details": "PERCENTYIELD", "is_desired": false}] | 100 | CELSIUS | 18 | HOUR | A solution of 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HBTU) (0.974 g, 2.57 mmol), 4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidineacetic acid (1.20 g, 2.57 mmol), and N,N-diisopropylethylamine (1.8 mL, 10.3 mmol) in N,N-dimethylformamide (15 mL) was stirred at room temperature f... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccc2c(c1)CCCC2.C1CC[NH]CC1.c1ccc2[nH]cnc2c1.c1ccncc1 | HO- | CN(C=O)C | 100 | 18 | COc1ccc2c(c1)CCC(N)C2Cc1cccnc1.Cl.O=C(O)CN1CCC(n2c(=O)[nH]c3ccccc32)CC1>CN(C=O)C>COc1ccc2c(c1)CC[C@H](NC(=O)CN1CCC(n3c(=O)[nH]c4ccccc43)CC1)[C@@H]2Cc1cccnc1.Cl |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-228917398cef42f3a34830673e83d2fe | COc1ccc2c(c1)CC[C@H](NC(=O)CN1CCC(n3c(=O)[nH]c4ccccc43)CC1)[C@@H]2Cc1cccnc1.Cl>>Cl.O=C(CN1CCC(n2c(=O)[nH]c3ccccc32)CC1)N[C@H]1CCc2cc(O)ccc2[C@H]1Cc1cccnc1 | CO.Cl.Cl.O=C1NC2=C(N1C1CCN(CC1)CC(=O)N[C@@H]1[C@@H](C3=CC=C(C=C3CC1)OC)CC=1C=NC=CC1)C=CC=C2.B(Br)(Br)Br>>Cl.Cl.O=C1NC2=C(N1C1CCN(CC1)CC(=O)N[C@@H]1[C@@H](C3=CC=C(C=C3CC1)O)CC=1C=NC=CC1)C=CC=C2 | C[O:29][c:28]1[cH:27][c:26]2[c:32]([cH:31][cH:30]1)[C@@H:33]([CH2:34][c:35]1[cH:36][cH:37][cH:38][n:39][cH:40]1)[C@@H:23]([NH:22][C:4](=[O:3])[CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([n:10]3[c:11](=[O:12])[nH:13][c:14]4[cH:15][cH:16][cH:17][cH:18][c:19]34)[CH2:20][CH2:21]1)[CH2:24][CH2:25]2.[ClH:1]>>[ClH:1].[O:3]=[C:4]([CH2:5... | COc1ccc2c(c1)CC[C@H](NC(=O)CN1CCC(n3c(=O)[nH]c4ccccc43)CC1)[C@@H]2Cc1cccnc1.Cl | Cl.O=C(CN1CCC(n2c(=O)[nH]c3ccccc32)CC1)N[C@H]1CCc2cc(O)ccc2[C@H]1Cc1cccnc1 | null | null | ClCCl | Miscellaneous | OtherReaction | 005318874c4792a3ed14897fb19099f1f6e548b285f476e19a15213a92356c2d | 0bab01685da92cdead9c84b3a9c513c0e9bd4114585991beae2460d8c47b3623 | O=C(CN1CCC(n2c(=O)[nH]c3ccccc32)CC1)N[C@H]1CCc2ccccc2[C@H]1Cc1cccnc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | 68 | [{"value": 68.0, "product": "Cl.Cl.O=C1NC2=C(N1C1CCN(CC1)CC(=O)N[C@@H]1[C@@H](C3=CC=C(C=C3CC1)O)CC=1C=NC=CC1)C=CC=C2", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 0.5 | HOUR | A solution of 4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-N-[cis-1,2,3,4-tetrahydro-6-methoxy-1-(3-pyridinylmethyl)-2-naphthalenyl]-1-piperidineacetamide 19 (0.28 g, 0.37 mmol) in dichloromethane (2 mL) was added dropwise to a solution of boron tribromide (1.8 mmol) in dichloromethane (22 mL) at 0° C. After stirring the... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | C1CC[NH]CC1.c1ccc2[nH]cnc2c1.c1ccc2c(c1)CCCC2.c1ccncc1 | Other | ClCCl | null | 0.5 | COc1ccc2c(c1)CC[C@H](NC(=O)CN1CCC(n3c(=O)[nH]c4ccccc43)CC1)[C@@H]2Cc1cccnc1.Cl>ClCCl>Cl.O=C(CN1CCC(n2c(=O)[nH]c3ccccc32)CC1)N[C@H]1CCc2cc(O)ccc2[C@H]1Cc1cccnc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-4ba49e669c8944568145ff09ba5e9264 | CC(=O)Cc1ccncc1>>C=CC(=O)Cc1cccnc1 | N1=CC=C(C=C1)CC(C)=O.FC=1C=C(C=O)C=CC1OC.N1CCCCC1>>N1=CC(=CC=C1)CC(C=C)=O | [CH3:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][n:10][cH:9][cH:11]1>>[CH2:1]=[CH:2][C:3](=[O:4])[CH2:5][c:6]1[cH:7][cH:8][cH:9][n:10][cH:11]1 | CC(=O)Cc1ccncc1 | C=CC(=O)Cc1cccnc1 | null | null | C1(=CC=CC=C1)C | Miscellaneous | OtherReaction | 58ac067248252835f00a3165c674651cacbcbd5887568465d5bc1f845a3f9fd5 | a4ea716c40716a0b7f0a729baa69598349e4dc3a183004a01a28b0d16986acd9 | c1ccncc1 | [CH3;D1;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[c:5]1:[c:6]:[cH;D2;+0:7]:[n;H0;D2;+0:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:1>>[C;D1;H2:11]=[CH;D2;+0:1]-[C:2](=[O;D1;H0:3])-[C:4]-[c:5]1:[c:6]:[cH;D2;+0:7]:[cH;D2;+0:9]:[n;H0;D2;+0:8]:[cH;D2;+0:10]:1 | 146.9 | [{"value": 80.0, "product": "N1=CC(=CC=C1)CC(C=C)=O", "details": "PERCENTYIELD", "is_desired": false}, {"value": 146.9, "product": "N1=CC(=CC=C1)CC(C=C)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 18 | HOUR | A solution of 4-pyridylacetone (1.0 g, 7.4 mmol), 3-fluoro-p-anisaldehyde (1.25 g, 8.1 mmol), and piperidine (0.13 g, 1.5 mmol) in toluene (50 ml) was heated to reflux. After 18 hours, the reaction was cooled to room temperature and the solvent was removed under reduced pressure. The crude product (3.0 g) was purified ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone.Vinyl | c1ccncc1 | c1ccncc1 | c1ccncc1 | Other | C1(=CC=CC=C1)C | null | 18 | CC(=O)Cc1ccncc1>C1(=CC=CC=C1)C>C=CC(=O)Cc1cccnc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ede2249cb08b4a579ea218c9296d4d94 | CC(=O)Cc1ccncc1.O=Cc1ccccc1>>CC(=O)C(=Cc1ccccc1)c1ccncc1 | N1=CC=C(C=C1)CC(C)=O.C(C1=CC=CC=C1)=O.N1CCCCC1>>C1(=CC=CC=C1)C=C(C(C)=O)C1=CC=NC=C1 | [CH3:1][C:2](=[O:3])[CH2:4][c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1.O=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1>>[CH3:1][C:2](=[O:3])[C:4](=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][n:15][cH:16][cH:17]1 | CC(=O)Cc1ccncc1.O=Cc1ccccc1 | CC(=O)C(=Cc1ccccc1)c1ccncc1 | null | null | C1=CC=CC=C1 | C-C Coupling | Aldol condensation | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | C(=Cc1ccncc1)c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[C;D1;H3:5]-[C:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1 | 78.7 | [{"value": 78.0, "product": "C1(=CC=CC=C1)C=C(C(C)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 78.7, "product": "C1(=CC=CC=C1)C=C(C(C)=O)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Example A-1, step 1, 4-pyridylacetone (step 1) (1 g, 7.4 mmol) was condensed with benzaldehyde (790 mg, 7.4 mmol) in benzene (15 mL) containing piperidine (50 mg) at reflux. The desired 4-phenyl-3-(4-pyridyl)-3-butene-2-one (1.3 g, 78%) was obtained as a crystalline solid: m. p. 101-103° C. Anal.... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccncc1 | HO- | C1=CC=CC=C1 | null | null | CC(=O)Cc1ccncc1.O=Cc1ccccc1>C1=CC=CC=C1>CC(=O)C(=Cc1ccccc1)c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f58e317b4f9744969269814759558a45 | CC(=O)C(=Cc1ccccc1)c1ccncc1.OO>>CC(=O)C1(c2ccncc2)OC1c1ccccc1 | C1(=CC=CC=C1)C=C(C(C)=O)C1=CC=NC=C1.OO.[OH-].[Na+]>>C1(=CC=CC=C1)C1C(C(C)=O)(O1)C1=CC=NC=C1 | [CH3:1][C:2](=[O:3])[C:4]([c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1)=[CH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1.O[OH:11]>>[CH3:1][C:2](=[O:3])[C:4]1([c:5]2[cH:6][cH:7][n:8][cH:9][cH:10]2)[O:11][CH:12]1[c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1 | CC(=O)C(=Cc1ccccc1)c1ccncc1.OO | CC(=O)C1(c2ccncc2)OC1c1ccccc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 5310d49b11c467cc6f2bb1b67ae31fe7fbc0be3f375d7a005d31b2362cbddf0d | 7ff20700d82072065bf203f7a44745e56ef236256026869b544d4eff6bac8783 | c1ccc(C2OC2c2ccncc2)cc1 | O-[OH;D1;+0:1].[C;D1;H3:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1>>[C;D1;H3:2]-[C:3](=[O;D1;H0:4])-[C;H0;D4;+0:5]1(-[c:10]2:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:2)-[O;H0;D2;+0:1]-[CH;D3;+0:6]-1-[c:7](:[c:8]):[c:9] | 20 | [{"value": 20.0, "product": "C1(=CC=CC=C1)C1C(C(C)=O)(O1)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Example A-1, step 2, a solution of 4-phenyl-3-(4-pyridyl)-3-butene-2-one (step 2) (1.25 g, 5.6 mmol) in methanol (20 ml) was treated with 30% aqueous hydrogen peroxide (1 ml) in the presence of sodium hydroxide (230 mg, 5.7 mmol). The crude product was purified by chromatography (silica gel, 1:1 ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Peroxide | Ketone.Ether | null | C1CO1 | c1ccncc1.C1CO1.c1ccccc1 | HO- | CO | null | null | CC(=O)C(=Cc1ccccc1)c1ccncc1.OO>CO>CC(=O)C1(c2ccncc2)OC1c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-69b96eedf34c4a37acb566602bfb5210 | CC(=O)C1(c2ccncc2)OC1c1ccccc1.NN>>Cc1n[nH]c(-c2ccccc2)c1-c1ccncc1 | C1(=CC=CC=C1)C1C(C(C)=O)(O1)C1=CC=NC=C1.NN>>CC1=NNC(=C1C1=CC=NC=C1)C1=CC=CC=C1 | O=[C:2]([CH3:1])[C:12]1([c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)O[CH:5]1[c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1.[NH2:3][NH2:4]>>[CH3:1][c:2]1[n:3][nH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[c:12]1-[c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1 | CC(=O)C1(c2ccncc2)OC1c1ccccc1.NN | Cc1n[nH]c(-c2ccccc2)c1-c1ccncc1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 3d767427471af8679ab96a9ef8b8a5608e72cdf8ed95f8ea7ae504a611c2b5b3 | bb1c7e9a3d57170de2c73b6fa3f5bc7c31ad9976d2759941c3ea46738c101a22 | c1ccc(-c2[nH]ncc2-c2ccncc2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;H0;D4;+0:3]1(-[c;H0;D3;+0:4]2:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:2)-O-[CH;D3;+0:10]-1-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15].[NH2;D1;+0:16]-[NH2;D1;+0:17]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[n;H0;D2;+0:16]:[nH;D2;+0:17]:[c;H0;D3;+0:10](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14]:[c:15]):[c;... | 35 | [{"value": 35.0, "product": "CC1=NNC(=C1C1=CC=NC=C1)C1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 34.4, "product": "CC1=NNC(=C1C1=CC=NC=C1)C1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | Using the procedure of Example A-1, step 3, a solution of 4-phenyl-3-(4-pyridyl)-3,4-epoxy-2-butanone (step 3) (250 mg, 1 mmol) in ethanol (15 ml) was treated with anhydrous hydrazine (50 mg, 1.5 mmol) and heated to reflux for 4 hours. The crude product was purified by chromatography (silica gel, 1:1 acetone/hexane). T... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ether | null | C1CO1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.c1ccncc1 | HO- | C(C)O | null | null | CC(=O)C1(c2ccncc2)OC1c1ccccc1.NN>C(C)O>Cc1n[nH]c(-c2ccccc2)c1-c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e6655c96939d4951a24c084af478a9ee | C1CCNCC1.Cc1ccccc1.Cc1ccccc1C=O>>CC(=O)C(=Cc1ccccc1C)c1ccncc1 | C1(=CC=CC=C1)C.C=1(C(=CC=CC1)C=O)C.N1CCCCC1.O>>CC1=C(C=CC=C1)C=C(C(C)=O)C1=CC=NC=C1 | [CH2:13]1[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]1.c1cc[cH:4][c:2]([CH3:1])c1.[O:3]=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[CH3:12]>>[CH3:1][C:2](=[O:3])[C:4](=[CH:5][c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[CH3:12])[c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1 | C1CCNCC1.Cc1ccccc1.Cc1ccccc1C=O | CC(=O)C(=Cc1ccccc1C)c1ccncc1 | null | null | null | C-C Coupling | OtherReaction | 9e5c85b79e15bdcaaf9e3ec702b4eda0aef404997135a9ecc0a250fe682cf221 | c2326e088efe6b686881bcc39eafc3fbffc8a8d1281e2dcdeecdd838d9d42f48 | C(=Cc1ccncc1)c1ccccc1 | [C;D1;H3:1]-[c;H0;D3;+0:2]1:[cH;D2;+0:3]:c:c:c:c:1.[CH2;D2;+0:4]1-[CH2;D2;+0:5]-[CH2;D2;+0:6]-[NH;D2;+0:7]-[CH2;D2;+0:8]-[CH2;D2;+0:9]-1.[O;H0;D1;+0:10]=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14]>>[C;D1;H3:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:10])-[C;H0;D3;+0:3](=[CH;D2;+0:11]-[c:12](:[c:13]):[c:14])-[c;H0;D3;+0:4]1:[cH;D2;+0:5]:[... | null | [] | null | null | 15 | HOUR | A solution of 4-pyrridylacetone (Example A-5, step 1) (0.75 g, 5.56 mmol), o-tolualdehyde (0.73 g, 5.56 mmol) and piperidine (100 mg) in toluene (50 ml) was heated to reflux. Water generated during the reaction was removed by a Dean-Stark trap. After heating at reflux for 5 hours, the reaction mixture was stirred at ro... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Secondary amine | Ketone | C1CCNCC1.c1ccccc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | Other | null | null | 15 | C1CCNCC1.Cc1ccccc1.Cc1ccccc1C=O>>CC(=O)C(=Cc1ccccc1C)c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fcfae01ee9d9406f8c01efe92ac822bc | CC(=O)C(=Cc1ccccc1C)c1ccncc1.OO>>CC(=O)C1(c2ccncc2)OC1c1ccccc1C | CC1=C(C=CC=C1)C=C(C(C)=O)C1=CC=NC=C1.OO.[OH-].[Na+]>>CC1=C(C=CC=C1)C1C(C(C)=O)(O1)C1=CC=NC=C1 | [CH3:1][C:2](=[O:3])[C:4]([c:5]1[cH:6][cH:7][n:8][cH:9][cH:10]1)=[CH:12][c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[CH3:19].O[OH:11]>>[CH3:1][C:2](=[O:3])[C:4]1([c:5]2[cH:6][cH:7][n:8][cH:9][cH:10]2)[O:11][CH:12]1[c:13]1[cH:14][cH:15][cH:16][cH:17][c:18]1[CH3:19] | CC(=O)C(=Cc1ccccc1C)c1ccncc1.OO | CC(=O)C1(c2ccncc2)OC1c1ccccc1C | null | null | O.CO | Heteroatom Alkylation and Arylation | OtherReaction | 5310d49b11c467cc6f2bb1b67ae31fe7fbc0be3f375d7a005d31b2362cbddf0d | 7ff20700d82072065bf203f7a44745e56ef236256026869b544d4eff6bac8783 | c1ccc(C2OC2c2ccncc2)cc1 | O-[OH;D1;+0:1].[C;D1;H3:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1>>[C;D1;H3:2]-[C:3](=[O;D1;H0:4])-[C;H0;D4;+0:5]1(-[c:10]2:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:2)-[O;H0;D2;+0:1]-[CH;D3;+0:6]-1-[c:7](:[c:8]):[c:9] | null | [] | null | null | 70 | HOUR | To a solution of 4-(2-methylphenyl)-3-(4-pyridyl)-3-butene-2-one (step 1) (1.0 g, 4.2 mmol) in methyl alcohol (18 ml), a solution of H2O2 (30% by wt.) (0.95 g, 8.4 mmol) and sodium hydroxide (0.18 g 4.6 mmol) in water (4 ml) was added. The reaction was stirred at room temperature for 70 hours. After methyl alcohol was ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Peroxide | Ketone.Ether | null | C1CO1 | c1ccncc1.C1CO1.c1ccccc1 | HO- | O.CO | null | 70 | CC(=O)C(=Cc1ccccc1C)c1ccncc1.OO>O.CO>CC(=O)C1(c2ccncc2)OC1c1ccccc1C |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8f872610fe0847baa821c66233be02f3 | CC(=O)C1(c2ccncc2)OC1c1ccccc1C.NN>>Cc1ccccc1-c1n[nH]c(C)c1-c1ccncc1 | CC1=C(C=CC=C1)C1C(C(C)=O)(O1)C1=CC=NC=C1.O.NN>>CC1=C(C(=NN1)C1=C(C=CC=C1)C)C1=CC=NC=C1 | O=[C:11]([CH3:12])[C:13]1([c:14]2[cH:15][cH:16][n:17][cH:18][cH:19]2)O[CH:8]1[c:7]1[c:2]([CH3:1])[cH:3][cH:4][cH:5][cH:6]1.[NH2:9][NH2:10]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][cH:6][c:7]1-[c:8]1[n:9][nH:10][c:11]([CH3:12])[c:13]1-[c:14]1[cH:15][cH:16][n:17][cH:18][cH:19]1 | CC(=O)C1(c2ccncc2)OC1c1ccccc1C.NN | Cc1ccccc1-c1n[nH]c(C)c1-c1ccncc1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 3d767427471af8679ab96a9ef8b8a5608e72cdf8ed95f8ea7ae504a611c2b5b3 | bb1c7e9a3d57170de2c73b6fa3f5bc7c31ad9976d2759941c3ea46738c101a22 | c1ccc(-c2n[nH]cc2-c2ccncc2)cc1 | O=[C;H0;D3;+0:1](-[C;D1;H3:2])-[C;H0;D4;+0:3]1(-[c;H0;D3;+0:4]2:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:2)-O-[CH;D3;+0:10]-1-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:14](-[C;D1;H3:15]):[c:16].[NH2;D1;+0:17]-[NH2;D1;+0:18]>>[C;D1;H3:2]-[c;H0;D3;+0:1]1:[nH;D2;+0:17]:[n;H0;D2;+0:18]:[c;H0;D3;+0:10](-[c;H0;D3;+0:11](:[c:12]:[c:13]):[c:... | null | [] | null | null | null | null | A solution of 4-(2-methylphenyl)-3-(4-pyridyl)-3,4-epoxy-2-butanone (step 2) (0.11 g, 0.434 mmol) and hydrazine hydrate (0.043 g, 0.868 mmol) in ethyl alcohol (50 ml) was heated at reflux for 20 hours. The solvent was removed and the resulting residue was purified by chromatography to give 4-[5-methyl-3-(2-methylphenyl... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ether | null | C1CO1 | c1cn[nH]c1 | c1ccccc1.c1cn[nH]c1.c1ccncc1 | HO- | C(C)O | null | null | CC(=O)C1(c2ccncc2)OC1c1ccccc1C.NN>C(C)O>Cc1ccccc1-c1n[nH]c(C)c1-c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6bc658d1bfb6474e966703232df05d6f | CC(C)(C)[Si](C)(C)Cl.OCCNN=C(Cc1ccncc1)c1ccc(F)cc1>>CC(C)(C)[Si](C)(C)OCCNN=C(Cc1ccncc1)c1ccc(F)cc1 | O.OCCNN=C(CC1=CC=NC=C1)C1=CC=C(C=C1)F.CC(C)(C)[Si](C)(C)Cl.N1C=NC=C1>>CC(C)(C)[Si](OCCNN=C(CC1=CC=NC=C1)C1=CC=C(C=C1)F)(C)C | Cl[Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7].[OH:8][CH2:9][CH2:10][NH:11][N:12]=[C:13]([CH2:14][c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1)[c:21]1[cH:22][cH:23][c:24]([F:25])[cH:26][cH:27]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH2:9][CH2:10][NH:11][N:12]=[C:13]([CH2:14][c:15]1[cH:16][... | CC(C)(C)[Si](C)(C)Cl.OCCNN=C(Cc1ccncc1)c1ccc(F)cc1 | CC(C)(C)[Si](C)(C)OCCNN=C(Cc1ccncc1)c1ccc(F)cc1 | null | null | CN(C)C=O | Protection | Alcohol protection with silyl ethers | 0085cd6629412592263fdf1537bdf8c19ef10dbeafe6f880807464d8107fa715 | d2a170d01b2f3ec57d6fac058519475050ba5531f5d304635fb42e153d5bb9b5 | N=C(Cc1ccncc1)c1ccccc1 | Cl-[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: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] | 98 | [{"value": 98.0, "product": "CC(C)(C)[Si](OCCNN=C(CC1=CC=NC=C1)C1=CC=C(C=C1)F)(C)C", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a solution of the 1-(4-fluorophenyl)-2-(4-pyridinyl)ethanone (2-hydroxyethyl)hydrazone prepared in step 1 (2.73 g, 0.01 mol) and (1,1-dimethylethyl)dimethylsilyl chloride (1.5 g, 0.01 mol) in 25 mL of DMF was added imidazole portionwise. The reaction mixture was stirred at room temperature overnight. Water was added... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol.Silyl protective group | TMS ether protective group | null | null | c1ccncc1.c1ccccc1 | HCl | CN(C)C=O | null | 8 | CC(C)(C)[Si](C)(C)Cl.OCCNN=C(Cc1ccncc1)c1ccc(F)cc1>CN(C)C=O>CC(C)(C)[Si](C)(C)OCCNN=C(Cc1ccncc1)c1ccc(F)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b730e5b337614438b0df825449c44415 | CC(C)(C)[Si](C)(C)OCCNN=C(Cc1ccncc1)c1ccc(F)cc1.COC(=O)C1CC1.C[Si](C)(C)[N-][Si](C)(C)C>>CC(C)(C)[Si](C)(C)OCCn1nc(-c2ccccc2)c(-c2ccccc2)c1C1CC1 | O.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].CC(C)(C)[Si](OCCNN=C(CC1=CC=NC=C1)C1=CC=C(C=C1)F)(C)C.C1(CC1)C(=O)OC>>C1(CC1)C1=C(C(=NN1CCO[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)C1=CC=CC=C1 | F[c:17]1[cH:16][cH:15][c:14]([C:13](=[N:12][NH:11][CH2:10][CH2:9][O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[CH2:20][c:21]2[cH:22][cH:23]n[cH:25][cH:26]2)[cH:19][cH:18]1.CO[C:27](=O)[CH:28]1[CH2:29][CH2:30]1.C[Si](C)(C)[N-][Si](C)(C)[CH3:24]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][... | CC(C)(C)[Si](C)(C)OCCNN=C(Cc1ccncc1)c1ccc(F)cc1.COC(=O)C1CC1.C[Si](C)(C)[N-][Si](C)(C)C | CC(C)(C)[Si](C)(C)OCCn1nc(-c2ccccc2)c(-c2ccccc2)c1C1CC1 | null | null | C1CCOC1 | Aromatic Heterocycle Formation | OtherReaction | a79510dbe8d2b107583dd2a869abb0ef04cea09d18876fd92cedec7cce043db7 | e9e76a09cea9281459d2ce0878168c17feadc9adf5b8840167b7710e55849787 | c1ccc(-c2n[nH]c(C3CC3)c2-c2ccccc2)cc1 | C-O-[C;H0;D3;+0:1](=O)-[C:2]1-[C:3]-[C:4]-1.C-[Si](-C)(-C)-[N-]-[Si](-C)(-C)-[CH3;D1;+0:5].F-[c;H0;D3;+0:6]1:[c:7]:[c:8]:[c;H0;D3;+0:9](-[C;H0;D3;+0:10](-[CH2;D2;+0:11]-[c;H0;D3;+0:12]2:[c:13]:[cH;D2;+0:14]:n:[cH;D2;+0:15]:[c:16]:2)=[N;H0;D2;+0:17]-[NH;D2;+0:18]-[C:19]-[C:20]):[c:21]:[c:22]:1>>[C:20]-[C:19]-[n;H0;D3;+0... | null | [] | null | null | 30 | MINUTE | To a solution of sodium hexamethyldisilazide (4.2 mL, 1.0 M in THF) at 0° C. was added a solution of the compound prepared in step 2 (0.78 g, 0.002 mol) in 10 mL of dry THF dropwise. The dark brown solution was stirred at this temperature for 30 minutes. Then a solution of methyl cyclopropanecarboxylate (0.27 g, 0.0026... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Aromatic halide.Ester.Silyl protective group.Silyl protective group | null | c1ccccc1.c1ccncc1 | c1cn[nH]c1.c1ccccc1.c1ccccc1 | c1cn[nH]c1.c1ccccc1.c1ccccc1.C1CC1 | HF | C1CCOC1 | null | 0.5 | CC(C)(C)[Si](C)(C)OCCNN=C(Cc1ccncc1)c1ccc(F)cc1.COC(=O)C1CC1.C[Si](C)(C)[N-][Si](C)(C)C>C1CCOC1>CC(C)(C)[Si](C)(C)OCCn1nc(-c2ccccc2)c(-c2ccccc2)c1C1CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c37dc49a47b5484cafb5f39fa2a2c164 | CCOC(=O)C1CC1c1c(-c2ccncc2)c(-c2ccc(F)cc2)nn1CCO>>O=C(O)C1CC1c1c(-c2ccncc2)c(-c2ccc(F)cc2)nn1CCO | [OH-].[Na+].FC1=CC=C(C=C1)C1=NN(C(=C1C1=CC=NC=C1)C1C(C1)C(=O)OCC)CCO.C1CCC(C1)NC2=NN=C(C3=CC(=C(C=C32)Cl)Cl)C4=CC=NC=C4>>FC1=CC=C(C=C1)C1=NN(C(=C1C1=CC=NC=C1)C1C(C1)C(=O)O)CCO | CC[O:3][C:2](=[O:1])[CH:4]1[CH2:5][CH:6]1[c:7]1[c:8](-[c:9]2[cH:10][cH:11][n:12][cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][c:19]([F:20])[cH:21][cH:22]2)[n:23][n:24]1[CH2:25][CH2:26][OH:27]>>[O:1]=[C:2]([OH:3])[CH:4]1[CH2:5][CH:6]1[c:7]1[c:8](-[c:9]2[cH:10][cH:11][n:12][cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][c:... | CCOC(=O)C1CC1c1c(-c2ccncc2)c(-c2ccc(F)cc2)nn1CCO | O=C(O)C1CC1c1c(-c2ccncc2)c(-c2ccc(F)cc2)nn1CCO | null | null | O.CO | Deprotection | Ester saponification (alkyl deprotection) | d872e08ad5c85a4add6cd04e6e987e73fead5f79b3f30ba61a81ba5029b29894 | 38ae1ee78433b9acfb0390501446149c80f88f23ac2d84c60b3369bdab75cec9 | c1ccc(-c2n[nH]c(C3CC3)c2-c2ccncc2)cc1 | C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]>>[C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1] | null | [] | null | null | null | null | To a solution of ethyl 2-[3-(4-fluorophenyl)-1-(2-hydroxyethyl)-4-(4-pyridinyl)-1H-pyrazol-5-yl]cyclopropanecarboxylate prepared in accordance with Example A-196 (0.21 g, 0.00045 mol) in 10 mL of methanol was added a solution of sodium hydroxide (0.09 g, 0.0022 mol) in 2 mL of water. The reaction mixture was stirred at... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Carboxylic acid | null | null | C1CC1.c1ccncc1.c1ccccc1.c1cn[nH]c1 | Other | O.CO | null | null | CCOC(=O)C1CC1c1c(-c2ccncc2)c(-c2ccc(F)cc2)nn1CCO>O.CO>O=C(O)C1CC1c1c(-c2ccncc2)c(-c2ccc(F)cc2)nn1CCO |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e4e13147fc66491b8f6fcad33de9cd9b | CN(C)C=O.COC(=O)c1c[nH]cn1.C[Si](C)(C)CCOCCl>>COC(=O)c1ccn(COCC[Si](C)(C)C)c1 | [H-].[Na+].CN(C)C=O.N1C=NC(=C1)C(=O)OC.C[Si](C)(C)CCOCCl>>C[Si](CCOCN1C=C(C=C1)C(=O)OC)(C)C | CN(C=O)[CH3:6].n1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:17][nH:8][cH:7]1.Cl[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:14])([CH3:15])[CH3:16]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][cH:7][n:8]([CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:14])([CH3:15])[CH3:16])[cH:17]1 | CN(C)C=O.COC(=O)c1c[nH]cn1.C[Si](C)(C)CCOCCl | COC(=O)c1ccn(COCC[Si](C)(C)C)c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 7c5e42e4ce8d87d0453b8cd9567e04cd94c920799410915227b31c72d98ffa60 | 2984e97dc99d59f23dc9b7338b3c1cfa8c682d0ec9c881b8c684e99fe044da2a | c1cc[nH]c1 | C-N(-[CH3;D1;+0:1])-C=O.Cl-[CH2;D2;+0:2]-[#8:3]-[C:4].[C;D1;H3:5]-[#8:6]-[C:7](=[O;D1;H0:8])-[c;H0;D3;+0:9]1:[c:10]:[nH;D2;+0:11]:[cH;D2;+0:12]:n:1>>[C:4]-[#8:3]-[CH2;D2;+0:2]-[n;H0;D3;+0:11]1:[c:10]:[c;H0;D3;+0:9](-[C:7](=[O;D1;H0:8])-[#8:6]-[C;D1;H3:5]):[cH;D2;+0:1]:[cH;D2;+0:12]:1 | null | [] | null | null | 0.5 | HOUR | To a suspension of sodium hydride (1.0 g, 0.025 mol) in 50 mL of DMF was added methyl 4-imidazolecarboxylate (2.95 g, 0.023 mol) portionwise at room temperature. The mixture was stirred at room temperature for 0.5 hours. Then SEM-CL (4.17 g, 0.025 mol) was added dropwise over 5 minutes. The reaction mixture was stirred... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ester.Ether.Tertiary amide | Ester.Ether | c1c[nH]cn1 | c1cc[nH]c1 | c1cc[nH]c1 | HCl | null | null | 0.5 | CN(C)C=O.COC(=O)c1c[nH]cn1.C[Si](C)(C)CCOCCl>>COC(=O)c1ccn(COCC[Si](C)(C)C)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-fb50f6cfbe3d4f45adc3c70edc36c9b3 | Cc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1.[O]=[Mn](=[O])(=[O])[O-].[O]=[Mn](=[O])(=[O])[O-]>>O=C(O)c1n[nH]c(-c2ccc(F)cc2)c1-c1ccncc1 | O.FC1=CC=C(C=C1)C1=NNC(=C1C1=CC=NC=C1)C.[Mn](=O)(=O)(=O)[O-].[K+].[Mn](=O)(=O)(=O)[O-].[K+]>>FC1=CC=C(C=C1)C1=C(C(=NN1)C(=O)O)C1=CC=NC=C1 | [CH3:2][c:4]1[nH:5][n:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[c:15]1-[c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1.[O]=[Mn](=[O])(=[O])[O-:3].[O]=[Mn](=[O])([O-])=[O:1]>>[O:1]=[C:2]([OH:3])[c:4]1[n:5][nH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]2)[c:15]1-[c:16]1[cH:17][cH:18][n:19][cH:20]... | Cc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1.[O]=[Mn](=[O])(=[O])[O-].[O]=[Mn](=[O])(=[O])[O-] | O=C(O)c1n[nH]c(-c2ccc(F)cc2)c1-c1ccncc1 | null | null | C(C)(C)(C)O | Acylation | OtherReaction | 7769a4cd09a67e270ac2d1d32df6b7a59b468ff590f9c59723b72ba3c8deb342 | 903e48d04e4504a4fe6977f5e5582144adff237d0488a4542a1907161cf0134c | c1ccc(-c2[nH]ncc2-c2ccncc2)cc1 | [CH3;D1;+0:1]-[c:2]1:[c:3]:[c:4](-[c:5]):[n;H0;D2;+0:6]:[nH;D2;+0:7]:1.[O-;H0;D1:8]-[Mn](=[O])(=[O])=[O].[O-]-[Mn](=[O;H0;D1;+0:9])(=[O])=[O]>>[O;H0;D1;+0:9]=[C;H0;D3;+0:1](-[OH;D1;+0:8])-[c:2]1:[c:3]:[c:4](-[c:5]):[nH;D2;+0:6]:[n;H0;D2;+0:7]:1 | null | [] | null | null | 8 | HOUR | A mixture of 4-[3-(4-fluorophenyl)-5-methyl-1H-pyrazol-4-yl]pyridine prepared as set forth in Example A-4 (5.83 g, 24.0909 mmol) and potassium permanganate (7.6916 g, 48.1818 mmol) in water (7.5 ml) and tert-butanol (10 ml) was heated at reflux for 6 hours (or until all the potassium permanganate was consumed). The mix... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | null | null | c1cn[nH]c1.c1ccccc1.c1ccncc1 | HO- | C(C)(C)(C)O | null | 8 | Cc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1.[O]=[Mn](=[O])(=[O])[O-].[O]=[Mn](=[O])(=[O])[O-]>C(C)(C)(C)O>O=C(O)c1n[nH]c(-c2ccc(F)cc2)c1-c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1cc31954fc634c00a423cc1613ed9fd0 | O=C(O)c1n[nH]c(-c2ccc(F)cc2)c1-c1ccncc1>>OCc1n[nH]c(-c2ccc(F)cc2)c1-c1ccncc1 | [H-].[Al+3].[Li+].[H-].[H-].[H-].O.FC1=CC=C(C=C1)C1=C(C(=NN1)C(=O)O)C1=CC=NC=C1.[OH-].[K+].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>FC1=CC=C(C=C1)C1=C(C(=NN1)CO)C1=CC=NC=C1 | O=[C:2]([OH:1])[c:3]1[n:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[c:14]1-[c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1>>[OH:1][CH2:2][c:3]1[n:4][nH:5][c:6](-[c:7]2[cH:8][cH:9][c:10]([F:11])[cH:12][cH:13]2)[c:14]1-[c:15]1[cH:16][cH:17][n:18][cH:19][cH:20]1 | O=C(O)c1n[nH]c(-c2ccc(F)cc2)c1-c1ccncc1 | OCc1n[nH]c(-c2ccc(F)cc2)c1-c1ccncc1 | null | null | O.C1CCOC1 | Reduction | Reduction of carboxylic acid to primary alcohol | 0db83a5ebe1e318b78b55461cf7eb8f7c004eef0f9e3b6666d3df4c96b5f665e | 93b4621647b04d2ad2f2825215b1567f171ba61fe10d136b5db6ea0470aa4932 | c1ccc(-c2[nH]ncc2-c2ccncc2)cc1 | O=[C;H0;D3;+0:1](-[O;D1;H1:2])-[c:3]1:[#7;a:4]:[#7;a:5]:[c:6]:[c:7]:1>>[O;D1;H1:2]-[CH2;D2;+0:1]-[c:3]1:[#7;a:4]:[#7;a:5]:[c:6]:[c:7]:1 | 56.5 | [{"value": 56.5, "product": "FC1=CC=C(C=C1)C1=C(C(=NN1)CO)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a suspension of 5-(4-fluorophenyl)-4-(4-pyridinyl)-1H-pyrazole-3-carboxylic acid, monohydrate prepared in accordance with Example A-200 (0.526 g, 2.0 mmol) in dry THF (15 ml) at reflux under nitrogen, a solution of 1N lithium aluminum hydride in THF (4.0 ml, 4.0 mmol) was added dropwise over 15 minutes. A precipitat... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Primary alcohol | null | null | c1cn[nH]c1.c1ccccc1.c1ccncc1 | Other | O.C1CCOC1 | null | null | O=C(O)c1n[nH]c(-c2ccc(F)cc2)c1-c1ccncc1>O.C1CCOC1>OCc1n[nH]c(-c2ccc(F)cc2)c1-c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f36b5071028046928e6e1687e3cb3bc8 | CCCCOC(=O)N1CCNCC1.CN(C)C=O.O=C(O)c1n[nH]c(-c2ccc(F)cc2)c1-c1ccncc1>>CC(C)(C)OC(=O)N1CCN(C(=O)c2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1 | C(CCC)OC(=O)N1CCNCC1.CN1CCOCC1.O.FC1=CC=C(C=C1)C1=C(C(=NN1)C(=O)O)C1=CC=NC=C1.ON1N=NC2=C1C=CC=C2.CN(C)C=O>>FC1=CC=C(C=C1)C1=C(C(=NN1)C(=O)N1CCN(CC1)C(=O)OC(C)(C)C)C1=CC=NC=C1 | C([CH3:1])[CH2:4][CH2:2][O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:32][CH2:33]1.CN(C=O)[CH3:3].O[C:12](=[O:13])[c:14]1[n:15][nH:16][c:17](-[c:18]2[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]2)[c:25]1-[c:26]1[cH:27][cH:28][n:29][cH:30][cH:31]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][... | CCCCOC(=O)N1CCNCC1.CN(C)C=O.O=C(O)c1n[nH]c(-c2ccc(F)cc2)c1-c1ccncc1 | CC(C)(C)OC(=O)N1CCN(C(=O)c2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1 | null | null | C(C)(=O)OCC | Acylation | OtherReaction | c909fd92dae84461bd7f8e029068785c25084aa8358fc8856c619817f749d07a | 96600684aa7d168a6aca35abaa2f4fdb56ee5830af274f4369f6150052490b6e | O=C(c1n[nH]c(-c2ccccc2)c1-c1ccncc1)N1CCNCC1 | C-N(-[CH3;D1;+0:1])-C=O.O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4]1:[#7;a:5]:[#7;a:6]:[c:7]:[c:8]:1.[CH3;D1;+0:9]-C-[CH2;D2;+0:10]-[CH2;D2;+0:11]-[#8:12]-[C:13](=[O;D1;H0:14])-[#7:15]1-[C:16]-[C:17]-[NH;D2;+0:18]-[C:19]-[C:20]-1>>[CH3;D1;+0:9]-[C;H0;D4;+0:11](-[CH3;D1;+0:1])(-[CH3;D1;+0:10])-[#8:12]-[C:13](=[O;D1;H0:14])-[#7... | 78.4 | [{"value": 78.4, "product": "FC1=CC=C(C=C1)C1=C(C(=NN1)C(=O)N1CCN(CC1)C(=O)OC(C)(C)C)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 0 | CELSIUS | 1 | HOUR | To a solution of 5-(4-fluorophenyl)-4-(4-pyridinyl)-1H-pyrazole-3-carboxylic acid, monohydrate prepared in accordance with Example A-200 (0.9905 g, 3.5 mmol) and 1-hydroxybenzotriazole (0.4824 g, 3.57 mmol) in DMF (20 ml) at 0° C. under nitrogen, 1-(3-dimethylaminopropyl)3-ethylcarbodiiminde hydrochloride (0.6984 g, 3.... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ether.Tertiary amide.Secondary amine | Ether.Tertiary amide.Boc | C1C[NH]CCN1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1cn[nH]c1.c1ccccc1.c1ccncc1 | HO- | C(C)(=O)OCC | 0 | 1 | CCCCOC(=O)N1CCNCC1.CN(C)C=O.O=C(O)c1n[nH]c(-c2ccc(F)cc2)c1-c1ccncc1>C(C)(=O)OCC>CC(C)(C)OC(=O)N1CCN(C(=O)c2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-42d6b0052f2c4a7aa5b1572e7f3072a3 | BrBr.Cn1cc(-c2ccncc2)c(-c2ccc(F)cc2)n1>>Cn1nc(-c2ccc(F)cc2)c(-c2ccncc2)c1Br | FC1=CC=C(C=C1)C1=NN(C=C1C1=CC=NC=C1)C.BrBr>>BrC1=C(C(=NN1C)C1=CC=C(C=C1)F)C1=CC=NC=C1 | Br[Br:20].[CH3:1][n:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]2)[c:12](-[c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[cH:19]1>>[CH3:1][n:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]2)[c:12](-[c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[c:19]1[Br:20] | BrBr.Cn1cc(-c2ccncc2)c(-c2ccc(F)cc2)n1 | Cn1nc(-c2ccc(F)cc2)c(-c2ccncc2)c1Br | null | null | C(C)(=O)O.CN(C)C=O | Functional Group Interconversion | Bromination | 62bd82ea16bda9045775280a9a6f541acc1cff475707d068db9b03a630cda50f | 3c4065ab4a8681675e06a527dcad54d701c7bfdcac9f73f87773b05034108934 | c1ccc(-c2n[nH]cc2-c2ccncc2)cc1 | Br-[Br;H0;D1;+0:1].[C;D1;H3:2]-[#7;a:3]1:[#7;a:4]:[c:5](-[c:6]):[c:7](-[c:8]):[cH;D2;+0:9]:1>>[Br;H0;D1;+0:1]-[c;H0;D3;+0:9]1:[#7;a:3](-[C;D1;H3:2]):[#7;a:4]:[c:5](-[c:6]):[c:7]:1-[c:8] | 35 | [{"value": 35.0, "product": "BrC1=C(C(=NN1C)C1=CC=C(C=C1)F)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 35.0, "product": "BrC1=C(C(=NN1C)C1=CC=C(C=C1)F)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | null | null | To a solution of 4-[3-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]pyridine (2.7 g, 10.67 mmol) (prepared in accordance with Example A-212) in acetic acid (30 mL) and DMF (13 mL) was added bromine (19.5 g, 122.0 mmol). The solution was heated at 60° C. overnight. TLC indicated that the reaction was complete. The mixture w... | 10.6084/m9.figshare.5104873.v1 | null | null | Aromatic halide | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.c1ccncc1 | HBr | C(C)(=O)O.CN(C)C=O | 60 | null | BrBr.Cn1cc(-c2ccncc2)c(-c2ccc(F)cc2)n1>C(C)(=O)O.CN(C)C=O>Cn1nc(-c2ccc(F)cc2)c(-c2ccncc2)c1Br |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3fcc306a9c4449289e94389f92b79ddf | Cn1nc(-c2ccc(F)cc2)c(-c2ccncc2)c1Br.O=Cc1ccccc1>>Cn1nc(-c2ccc(F)cc2)c(-c2ccncc2)c1C(O)c1ccccc1 | [Mg].BrC1=C(C(=NN1C)C1=CC=C(C=C1)F)C1=CC=NC=C1.C(C1=CC=CC=C1)=O>>FC1=CC=C(C=C1)C1=NN(C(=C1C1=CC=NC=C1)C(O)C1=CC=CC=C1)C | Br[c:19]1[n:2]([CH3:1])[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]2)[c:12]1-[c:13]1[cH:14][cH:15][n:16][cH:17][cH:18]1.[CH:20](=[O:21])[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][n:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([F:9])[cH:10][cH:11]2)[c:12](-[c:13]2[cH:14][cH:15][n:16][cH:17][cH:18]2)[c:19... | Cn1nc(-c2ccc(F)cc2)c(-c2ccncc2)c1Br.O=Cc1ccccc1 | Cn1nc(-c2ccc(F)cc2)c(-c2ccncc2)c1C(O)c1ccccc1 | null | null | O1CCCC1 | C-C Coupling | Grignard_alcohol | a9dcf423fb5579f063fb57c4002a18e05872015bf82eb9caf581a96204c0493e | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(Cc2[nH]nc(-c3ccccc3)c2-c2ccncc2)cc1 | Br-[c;H0;D3;+0:1]1:[#7;a:2](-[C;D1;H3:3]):[#7;a:4]:[c:5](-[c:6]):[c:7]:1-[c:8].[O;H0;D1;+0:9]=[CH;D2;+0:10]-[c:11](:[c:12]):[c:13]>>[C;D1;H3:3]-[#7;a:2]1:[#7;a:4]:[c:5](-[c:6]):[c:7](-[c:8]):[c;H0;D3;+0:1]:1-[CH;D3;+0:10](-[OH;D1;+0:9])-[c:11](:[c:12]):[c:13] | 12 | [{"value": 12.0, "product": "FC1=CC=C(C=C1)C1=NN(C(=C1C1=CC=NC=C1)C(O)C1=CC=CC=C1)C", "details": "PERCENTYIELD", "is_desired": false}] | 40 | CELSIUS | null | null | To solid magnesium (60 mg, 5 mmol) under nitrogen was added a solution of 4-[5-bromo-3-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]pyridine (450 mg, 1.35 mmol) (prepared in accordance with Example A-214) in tetrahydrofuran (7 mL). The mixture was heated at 40° C. for 2 hours. Benzaldehyde (1 mL) was added. The mixture wa... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1cn[nH]c1 | c1cn[nH]c1 | c1cn[nH]c1.c1ccccc1.c1ccncc1.c1ccccc1 | Br- | O1CCCC1 | 40 | null | Cn1nc(-c2ccc(F)cc2)c(-c2ccncc2)c1Br.O=Cc1ccccc1>O1CCCC1>Cn1nc(-c2ccc(F)cc2)c(-c2ccncc2)c1C(O)c1ccccc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-1c08ee51d78245dbbfb5572cd408d2d8 | CN(C)C(OC(C)(C)C)N(C)C.Cc1ccnc(Br)c1>>CN(C)/C=C/c1ccnc(Br)c1.Cc1ccnc(Br)c1 | CC1=CC(=NC=C1)Br.C(C)(C)(C)OC(N(C)C)N(C)C>>CC1=CC(=NC=C1)Br.BrC1=NC=CC(=C1)/C=C/N(C)C | O([CH:4]([N:2]([CH3:1])[CH3:3])[N:17]([CH3:16])[CH3:18])[C:14]([CH3:13])([CH3:15])[CH3:20].[CH3:5][c:6]1[cH:7][cH:8][n:9][c:10]([Br:11])[cH:12]1>>[CH3:1][N:2]([CH3:3])/[CH:4]=[CH:5]/[c:6]1[cH:7][cH:8][n:9][c:10]([Br:11])[cH:12]1.[CH3:13][c:14]1[cH:15][cH:16][n:17][c:18]([Br:19])[cH:20]1 | CN(C)C(OC(C)(C)C)N(C)C.Cc1ccnc(Br)c1 | CN(C)/C=C/c1ccnc(Br)c1.Cc1ccnc(Br)c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | fb4c51aec19f24da9bb69263455ca40f02e025a61b854e9b0c007a8d0f5b9341 | fbe49a0e081bcdf53905cf8a3d57c67bfe6297c0544f2c3236f9be6fefa0316d | c1ccncc1.c1ccncc1 | [C;D1;H3:1]-[C;H0;D4;+0:2](-[CH3;D1;+0:3])(-[CH3;D1;+0:4])-O-[CH;D3;+0:5](-[#7:6](-[C;D1;H3:7])-[C;D1;H3:8])-[N;H0;D3;+0:9](-[CH3;D1;+0:10])-[CH3;D1;+0:11].[CH3;D1;+0:12]-[c:13]1:[c:14]:[c:15]:[#7;a:16]:[c:17]:[c:18]:1>>[Br;D1;H0:19]-[c;H0;D3;+0:11]1:[cH;D2;+0:4]:[c;H0;D3;+0:2](-[C;D1;H3:1]):[cH;D2;+0:3]:[cH;D2;+0:10]:... | null | [] | null | null | null | null | 4-Methyl-2-bromopyridine (1.0 g, 5.8 mmol) and t-butoxybis(dimethylamino)methane (5 ml) were heated to 150° C. for 16 hours. 4-Methyl-2-bromopyridine was prepared as set forth in B. Adger et al., J. Chem. Soc., Perkin Trans. 1, pp. 2791-2796 (1988), which is incorporated herein by reference. The contents were evaporate... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Tertiary amine | Enamine.Aromatic halide | null | c1ccncc1 | c1ccncc1.c1ccncc1 | null | null | null | null | CN(C)C(OC(C)(C)C)N(C)C.Cc1ccnc(Br)c1>>CN(C)/C=C/c1ccnc(Br)c1.Cc1ccnc(Br)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-52f9731d22ea41209e8550b5e70cad66 | CN(C)/C=C(\C(=O)c1cccc(Cl)c1)c1ccnc(Br)c1.NN>>Clc1cccc(-c2n[nH]cc2-c2ccnc(Br)c2)c1 | BrC1=NC=CC(=C1)/C(/C(=O)C1=CC(=CC=C1)Cl)=C/N(C)C.O.NN>>BrC1=NC=CC(=C1)C=1C(=NNC1)C1=CC(=CC=C1)Cl | CN(C)/[CH:10]=[C:11](\[C:7](=O)[c:6]1[cH:5][cH:4][cH:3][c:2]([Cl:1])[cH:19]1)[c:12]1[cH:13][cH:14][n:15][c:16]([Br:17])[cH:18]1.[NH2:8][NH2:9]>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][nH:9][cH:10][c:11]2-[c:12]2[cH:13][cH:14][n:15][c:16]([Br:17])[cH:18]2)[cH:19]1 | CN(C)/C=C(\C(=O)c1cccc(Cl)c1)c1ccnc(Br)c1.NN | Clc1cccc(-c2n[nH]cc2-c2ccnc(Br)c2)c1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | dfa2b000ac131205a53cbf7deffa11f27024f31fbf093f64d70ab7e9db936435 | 5904d01f33f3f511a876efed92dcef694c128bcdc48700898ac39b754505c633 | c1ccc(-c2n[nH]cc2-c2ccncc2)cc1 | C-N(-C)/[CH;D2;+0:1]=[C;H0;D3;+0:2](\[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])-[c;H0;D3;+0:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13](-[Br;D1;H0:14]):[c:15]:1.[NH2;D1;+0:16]-[NH2;D1;+0:17]>>[Br;D1;H0:14]-[c:13]1:[#7;a:12]:[c:11]:[c:10]:[c;H0;D3;+0:9](-[c;H0;D3;+0:2]2:[cH;D2;+0:1]:[nH;D2;+0:17]:[n;H0;D2;+0:16... | 31.5 | [{"value": 31.0, "product": "BrC1=NC=CC(=C1)C=1C(=NNC1)C1=CC(=CC=C1)Cl", "details": "PERCENTYIELD", "is_desired": false}, {"value": 31.5, "product": "BrC1=NC=CC(=C1)C=1C(=NNC1)C1=CC(=CC=C1)Cl", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the product from step 2 (650 mg, 1.8 mmol) and hydrazine monohydrate (100 mg) in ethanol (10 ml) was refluxed for 24 hours. Solvent was evaporated and the residue was chromatographed on silica gel using mixtures of ethyl acetate and toluene as eluents to give 2-bromo-4-(3-(3-chlorophenyl)-1H-pyrazol-4-yl]... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Hydrazine.Ketone | null | null | c1cn[nH]c1 | c1ccccc1.c1cn[nH]c1.c1ccncc1 | HO- | C(C)O | null | null | CN(C)/C=C(\C(=O)c1cccc(Cl)c1)c1ccnc(Br)c1.NN>C(C)O>Clc1cccc(-c2n[nH]cc2-c2ccnc(Br)c2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-805e8a619eca4ce6bf9ab6f1424716a9 | NN=c1cc(-c2c[nH]nc2-c2cccc(Cl)c2)cc[nH]1>>Clc1cccc(-c2n[nH]cc2-c2ccnc(NCc3ccccc3)c2)c1 | ClC=1C=C(C=CC1)C1=NNC=C1C1=CC(NC=C1)=NN>>ClC=1C=C(C=CC1)C1=NNC=C1C1=CC(=NC=C1)NCC1=CC=CC=C1 | N[N:17]=[c:16]1[nH:15][cH:14][cH:13][c:12](-[c:11]2[c:7](-[c:6]3[cH:5][cH:4][cH:3][c:2]([Cl:1])[cH:26]3)[n:8][nH:9][cH:10]2)[cH:25]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][nH:9][cH:10][c:11]2-[c:12]2[cH:13][cH:14][n:15][c:16]([NH:17][CH2:18][c:19]3[cH:20][cH:21][cH:22][cH:23][cH:24]3)[cH:25]2)[cH:26]1 | NN=c1cc(-c2c[nH]nc2-c2cccc(Cl)c2)cc[nH]1 | Clc1cccc(-c2n[nH]cc2-c2ccnc(NCc3ccccc3)c2)c1 | null | null | C(C1=CC=CC=C1)N | Aromatic Heterocycle Formation | OtherReaction | 78ab757a26a83873db78c850941655096b12e1a71e064e5bc1dcc6122f9f5c93 | fcfdaaee7721f8ca8af96a4ef99464dd31764b71786fa1482394754d563f919f | c1ccc(CNc2cc(-c3c[nH]nc3-c3ccccc3)ccn2)cc1 | N-[N;H0;D2;+0:1]=[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1>>[c:8]-[C:9]-[NH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[n;H0;D2;+0:7]:1 | 121.9 | [{"value": 61.0, "product": "ClC=1C=C(C=CC1)C1=NNC=C1C1=CC(=NC=C1)NCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 121.9, "product": "ClC=1C=C(C=CC1)C1=NNC=C1C1=CC(=NC=C1)NCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the bromopyridine compound prepared in step 3 of Example A-219 (150 mg, 0.5 mmol) in benzylamine (5 ml) was heated at 175° C. for six hours. After cooling, excess benzylamine was removed by high vacuum distillation and ethyl acetate added to the residue. After washing the organic phase with water and dryi... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone | Secondary amine | c1ccncc1 | c1ccncc1.c1ccccc1 | c1ccccc1.c1cn[nH]c1.c1ccncc1.c1ccccc1 | null | C(C1=CC=CC=C1)N | null | null | NN=c1cc(-c2c[nH]nc2-c2cccc(Cl)c2)cc[nH]1>C(C1=CC=CC=C1)N>Clc1cccc(-c2n[nH]cc2-c2ccnc(NCc3ccccc3)c2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b118a07e98b94ec0b7cc0223ff7ca087 | NN=c1cc(-c2c[nH]nc2-c2cccc(Cl)c2)cc[nH]1>>Clc1cccc(-c2n[nH]cc2-c2ccnc(NCCc3ccccc3)c2)c1 | ClC=1C=C(C=CC1)C1=NNC=C1C1=CC(NC=C1)=NN>>ClC=1C=C(C=CC1)C1=NNC=C1C1=CC(=NC=C1)NCCC1=CC=CC=C1 | N[N:17]=[c:16]1[nH:15][cH:14][cH:13][c:12](-[c:11]2[c:7](-[c:6]3[cH:5][cH:4][cH:3][c:2]([Cl:1])[cH:27]3)[n:8][nH:9][cH:10]2)[cH:26]1>>[Cl:1][c:2]1[cH:3][cH:4][cH:5][c:6](-[c:7]2[n:8][nH:9][cH:10][c:11]2-[c:12]2[cH:13][cH:14][n:15][c:16]([NH:17][CH2:18][CH2:19][c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[cH:26]2)[cH:27]... | NN=c1cc(-c2c[nH]nc2-c2cccc(Cl)c2)cc[nH]1 | Clc1cccc(-c2n[nH]cc2-c2ccnc(NCCc3ccccc3)c2)c1 | null | null | C(CC1=CC=CC=C1)N | Aromatic Heterocycle Formation | OtherReaction | 78ab757a26a83873db78c850941655096b12e1a71e064e5bc1dcc6122f9f5c93 | fcfdaaee7721f8ca8af96a4ef99464dd31764b71786fa1482394754d563f919f | c1ccc(CCNc2cc(-c3c[nH]nc3-c3ccccc3)ccn2)cc1 | N-[N;H0;D2;+0:1]=[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[nH;D2;+0:7]:1>>[C:8]-[C:9]-[NH;D2;+0:1]-[c;H0;D3;+0:2]1:[c:3]:[c:4]:[c:5]:[c:6]:[n;H0;D2;+0:7]:1 | 163.6 | [{"value": 81.0, "product": "ClC=1C=C(C=CC1)C1=NNC=C1C1=CC(=NC=C1)NCCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 163.6, "product": "ClC=1C=C(C=CC1)C1=NNC=C1C1=CC(=NC=C1)NCCC1=CC=CC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the bromopyridine compound prepared in step 3 of Example A-219 (250 mg, 0.75 mmol) in phenethylamine (5 ml) was heated at 175° C. for six hours under a nitrogen atmosphere. The excess amine was distilled off under high vacuum and the residue was dissolved in ethyl acetate and washed with water. After dryi... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone | Secondary amine | c1ccncc1 | c1ccncc1.c1ccccc1 | c1ccccc1.c1cn[nH]c1.c1ccncc1.c1ccccc1 | null | C(CC1=CC=CC=C1)N | null | null | NN=c1cc(-c2c[nH]nc2-c2cccc(Cl)c2)cc[nH]1>C(CC1=CC=CC=C1)N>Clc1cccc(-c2n[nH]cc2-c2ccnc(NCCc3ccccc3)c2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-ac2c04c0de4642518cbd5506b709b302 | CCN.NN=c1cc(-c2c[nH]nc2-c2cccc(Cl)c2)cc[nH]1>>CCNc1cc(-c2c[nH]nc2-c2cccc(Cl)c2)ccn1 | ClC=1C=C(C=CC1)C1=NNC=C1C1=CC(NC=C1)=NN.C(C)N>>ClC=1C=C(C=CC1)C1=NNC=C1C1=CC(=NC=C1)NCC | [CH3:1][CH2:2][NH2:3].NN=[c:4]1[cH:5][c:6](-[c:7]2[cH:8][nH:9][n:10][c:11]2-[c:12]2[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]2)[cH:19][cH:20][nH:21]1>>[CH3:1][CH2:2][NH:3][c:4]1[cH:5][c:6](-[c:7]2[cH:8][nH:9][n:10][c:11]2-[c:12]2[cH:13][cH:14][cH:15][c:16]([Cl:17])[cH:18]2)[cH:19][cH:20][n:21]1 | CCN.NN=c1cc(-c2c[nH]nc2-c2cccc(Cl)c2)cc[nH]1 | CCNc1cc(-c2c[nH]nc2-c2cccc(Cl)c2)ccn1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 3770d647e174bb367c3dad1a16aec780a9d143a2723b6680d9719dcab7945370 | a2cc61f64635a67d464928ccd0df2bfeb2b24dd9e52bbc1660da6cc142ef8b59 | c1ccc(-c2n[nH]cc2-c2ccncc2)cc1 | N-N=[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[nH;D2;+0:6]:1.[C;D1;H3:7]-[C:8]-[NH2;D1;+0:9]>>[C;D1;H3:7]-[C:8]-[NH;D2;+0:9]-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[c:5]:[n;H0;D2;+0:6]:1 | 46 | [{"value": 46.0, "product": "ClC=1C=C(C=CC1)C1=NNC=C1C1=CC(=NC=C1)NCC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the bromopyridine compound prepared in step 3 of Example A-219 (300 mg, 0.9 mmol) in ethylamine (3.5 ml) and ethanol (5 ml) as heated at 150° C. in a sealed tube for 9 hours. The solvent was removed in vacuo and the residue chromatographed on silica gel with 70 ethyl acetate/30 toluene to give 4-[3-(3-chl... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazone.Primary amine | Secondary amine | c1ccncc1 | c1ccncc1 | c1ccncc1.c1cn[nH]c1.c1ccccc1 | Other | C(C)O | null | null | CCN.NN=c1cc(-c2c[nH]nc2-c2cccc(Cl)c2)cc[nH]1>C(C)O>CCNc1cc(-c2c[nH]nc2-c2cccc(Cl)c2)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b34faaad8aa14c18968d85846f049561 | N#Cc1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1.OO>>NC(=O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1 | O.FC1=CC=C(C=C1)C1=NNC=C1C1=CC(=NC=C1)C#N.OO.C([O-])([O-])=O.[K+].[K+]>>FC1=CC=C(C=C1)C1=NNC=C1C1=CC(=NC=C1)C(=O)N | [N:1]#[C:2][c:4]1[cH:5][c:6](-[c:7]2[cH:8][nH:9][n:10][c:11]2-[c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)[cH:19][cH:20][n:21]1.O[OH:3]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][nH:9][n:10][c:11]2-[c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)[cH:19][cH:20][n:21]1 | N#Cc1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1.OO | NC(=O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1 | null | null | CS(=O)C | Heteroatom Alkylation and Arylation | Nitrile and hydrogen peroxide to amide | b438c1a5a5f49012c6adf1e24ab44bc669089beaf4e5b0289cbfa931d3ceafda | 37ed9176b981633816a0414a3f5b39ee33c11d757fe87a2cac8fe30b523bffdf | c1ccc(-c2n[nH]cc2-c2ccncc2)cc1 | O-[OH;D1;+0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4](:[c:5]):[#7;a:6]:[c:7]>>[NH2;D1;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4](:[c:5]):[#7;a:6]:[c:7] | 283.4 | [{"value": 67.0, "product": "FC1=CC=C(C=C1)C1=NNC=C1C1=CC(=NC=C1)C(=O)N", "details": "PERCENTYIELD", "is_desired": false}, {"value": 283.4, "product": "FC1=CC=C(C=C1)C1=NNC=C1C1=CC(=NC=C1)C(=O)N", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1 | HOUR | To a solution of 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyridinecarbonitrile from step 2 (0.45 g, 0.0017 mol) in 10 mL of DMSO was added hydrogen peroxide (0.24 mL of 30% aqueous solution, 1.7 mmol) and potassium carbonate (0.04 g, 0.4 mmol) at 0° C. The mixture was stirred for 1 hour while allowing it to warm to roo... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile.Peroxide | Primary amide | null | null | c1ccncc1.c1cn[nH]c1.c1ccccc1 | Other | CS(=O)C | null | 1 | N#Cc1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1.OO>CS(=O)C>NC(=O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-60cddbfe744d4b25a0c0e3447c68e8b0 | COC(OC)N(C)C.NC(=O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1>>COC(=O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1 | FC1=CC=C(C=C1)C1=NNC=C1C1=CC(=NC=C1)C(=O)N.COC(N(C)C)OC>>FC1=CC=C(C=C1)C1=NNC=C1C1=CC(=NC=C1)C(=O)OC | COC(N(C)C)[O:2][CH3:1].N[C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][nH:10][n:11][c:12]2-[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[cH:20][cH:21][n:22]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][nH:10][n:11][c:12]2-[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[cH:20][cH:21][n:22]1 | COC(OC)N(C)C.NC(=O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1 | COC(=O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1 | null | null | CO | Acylation | OtherReaction | 595d6bd126de87caac15f4e8c9976d7f117bf8a94adb3dc2e6e2e4c519efe623 | a5f18927c129d13b1e22363113e65847b548ef26b7e04f9d405e8894819737be | c1ccc(-c2n[nH]cc2-c2ccncc2)cc1 | C-O-C(-[O;H0;D2;+0:1]-[C;D1;H3:2])-N(-C)-C.N-[C;H0;D3;+0:3](=[O;D1;H0:4])-[c:5](:[c:6]):[#7;a:7]:[c:8]>>[C;D1;H3:2]-[O;H0;D2;+0:1]-[C;H0;D3;+0:3](=[O;D1;H0:4])-[c:5](:[c:6]):[#7;a:7]:[c:8] | 69 | [{"value": 69.0, "product": "FC1=CC=C(C=C1)C1=NNC=C1C1=CC(=NC=C1)C(=O)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | To a suspension of 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyridinecarboxamide prepared as set forth in Example A-223 (2.9 g, 0.01 mol) in 50 mL of methanol was added N,N-dimethylformamide dimethyl acetal (3.67 g, 0.03 mol) dropwise. The reaction mixture was stirred at room temperature overnight and heated at reflux f... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether.Primary amide.Tertiary amine | Ester | null | null | c1ccncc1.c1cn[nH]c1.c1ccccc1 | HO- | CO | null | 8 | COC(OC)N(C)C.NC(=O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1>CO>COC(=O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-48bc566224a84ed6a6938877093be0f6 | CN.COC(=O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1>>CNC(=O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1 | FC1=CC=C(C=C1)C1=NNC=C1C1=CC(=NC=C1)C(=O)OC.CN>>FC1=CC=C(C=C1)C1=NNC=C1C1=CC(=NC=C1)C(=O)NC | [CH3:1][NH2:2].CO[C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][nH:10][n:11][c:12]2-[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[cH:20][cH:21][n:22]1>>[CH3:1][NH:2][C:3](=[O:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][nH:10][n:11][c:12]2-[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[cH:20][cH:21][n:22]1 | CN.COC(=O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1 | CNC(=O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1 | null | null | O | Acylation | Aminolysis of esters | 04c54ce22aa9bc0cea0de3d900446bcab51cf02bebeb606fa788a47dcd0e37ff | 4335147c9ad02004b7c12428d7eac0b2e7e0e2017adc471d01c387239de8017d | c1ccc(-c2n[nH]cc2-c2ccncc2)cc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6].[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[#7;a:5]:[c:6] | null | [] | 120 | CELSIUS | null | null | A mixture of methyl 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyridinecarboxylate prepared as set forth in Example A-224 (0.45 g, 1.5 mmol) and 20 mL of methylamine (40% aqueous solution) was heated at 120° C. in a sealed tube for 16 hours. After cooling, water was added and the aqueous phase was extracted with ethyl ac... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Primary amine | Secondary amide | null | null | c1ccncc1.c1cn[nH]c1.c1ccccc1 | HO- | O | 120 | null | CN.COC(=O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1>O>CNC(=O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-921dbc232a2141aa8b536cfbd0a60f74 | O=C([O-])c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1>>O=C(O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1 | FC1=CC=C(C=C1)C1=NNC=C1C1=CC(=NC=C1)C(=O)[O-].[OH-].[Na+]>>FC1=CC=C(C=C1)C1=NNC=C1C1=CC(=NC=C1)C(=O)O | [O:1]=[C:2]([O-:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][nH:9][n:10][c:11]2-[c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)[cH:19][cH:20][n:21]1>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][nH:9][n:10][c:11]2-[c:12]2[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]2)[cH:19][cH:20][n:21]1 | O=C([O-])c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1 | O=C(O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1 | null | null | O.C(C)O | Reduction | Carboxylate to carboxylic acid | 65edb34f59b888c9ecb87d6c8e9fd76d082de6afc49403d96c457f834c73148e | 222e2311064b3cb906d6bdeba44711f5dada050c096bbbcc7b35038975f228e8 | c1ccc(-c2n[nH]cc2-c2ccncc2)cc1 | [#7;a:1]:[c:2]-[C:3](-[O-;H0;D1:4])=[O;D1;H0:5]>>[#7;a:1]:[c:2]-[C:3](=[O;D1;H0:5])-[OH;D1;+0:4] | 73 | [{"value": 73.0, "product": "FC1=CC=C(C=C1)C1=NNC=C1C1=CC(=NC=C1)C(=O)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyridinecarboxylate prepared as set forth in Example A-224 (0.90 g, 0.003 mol) in 10 mL of ethanol was added a solution of sodium hydroxide (0.24 g, 0.006 mol) in 5 mL of water. The reaction mixture was heated at reflux for 10 hours. After the removal of solvent... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | null | null | c1ccncc1.c1cn[nH]c1.c1ccccc1 | null | O.C(C)O | null | null | O=C([O-])c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1>O.C(C)O>O=C(O)c1cc(-c2c[nH]nc2-c2ccc(F)cc2)ccn1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-557205710d604952badc543a9a9745f7 | COC(OC)N(C)C.O=C(Cc1ccnc(Cl)n1)c1ccc(F)cc1>>CN(C)/C=C(/C(=O)c1ccc(F)cc1)c1ccnc(Cl)n1 | ClC1=NC=CC(=N1)CC(=O)C1=CC=C(C=C1)F.COC(N(C)C)OC>>ClC1=NC=CC(=N1)/C(/C(=O)C1=CC=C(C=C1)F)=C\N(C)C | CO[CH:4](OC)[N:2]([CH3:1])[CH3:3].[CH2:5]([C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1)[c:15]1[cH:16][cH:17][n:18][c:19]([Cl:20])[n:21]1>>[CH3:1][N:2]([CH3:3])/[CH:4]=[C:5](/[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11]([F:12])[cH:13][cH:14]1)[c:15]1[cH:16][cH:17][n:18][c:19]([Cl:20])[n:21]1 | COC(OC)N(C)C.O=C(Cc1ccnc(Cl)n1)c1ccc(F)cc1 | CN(C)/C=C(/C(=O)c1ccc(F)cc1)c1ccnc(Cl)n1 | null | null | null | C-C Coupling | OtherReaction | 57f48fac7254684faf48980af66a0d538cb8dee0ab05f049059285d4840b8be4 | 49ae3600e90e05c7cda8811d9438748b91211f407b3eab7b1bcb51e798f4d85a | [CH]=C(C(=O)c1ccccc1)c1ccncn1 | C-O-[CH;D3;+0:1](-O-C)-[#7:2](-[C;D1;H3:3])-[C;D1;H3:4].[O;D1;H0:5]=[C:6](-[c:7])-[CH2;D2;+0:8]-[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[C;D1;H3:3]-[#7:2](-[C;D1;H3:4])/[CH;D2;+0:1]=[C;H0;D3;+0:8](/[C:6](=[O;D1;H0:5])-[c:7])-[c:9]1:[#7;a:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1 | null | [] | null | null | 8 | HOUR | A mixture of the compound prepared in step 2 (4.7 g, 0.017 mol) in 100 mL of dimethylformamide dimethyl acetal was stirred at room temperature overnight. Excess dimethylformamide dimethyl acetal was removed under vacuum to give 4.5 g of crude product as a thick brown oil, which was used without further purification.
Co... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ether.Ether | Enamine | null | null | c1ccccc1.c1cncnc1 | HO- | null | null | 8 | COC(OC)N(C)C.O=C(Cc1ccnc(Cl)n1)c1ccc(F)cc1>>CN(C)/C=C(/C(=O)c1ccc(F)cc1)c1ccnc(Cl)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-444fac7d088041daa1c2a3c8dd57edce | CN(C)/C=C(/C(=O)c1ccc(F)cc1)c1ccnc(Cl)n1.NN>>Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1 | ClC1=NC=CC(=N1)/C(/C(=O)C1=CC=C(C=C1)F)=C\N(C)C.O.NN>>ClC1=NC=CC(=N1)C=1C(=NNC1)C1=CC=C(C=C1)F | CN(C)/[CH:9]=[C:10](/[C:6](=O)[c:5]1[cH:4][cH:3][c:2]([F:1])[cH:19][cH:18]1)[c:11]1[cH:12][cH:13][n:14][c:15]([Cl:16])[n:17]1.[NH2:7][NH2:8]>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][nH:8][cH:9][c:10]2-[c:11]2[cH:12][cH:13][n:14][c:15]([Cl:16])[n:17]2)[cH:18][cH:19]1 | CN(C)/C=C(/C(=O)c1ccc(F)cc1)c1ccnc(Cl)n1.NN | Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | dfa2b000ac131205a53cbf7deffa11f27024f31fbf093f64d70ab7e9db936435 | 5904d01f33f3f511a876efed92dcef694c128bcdc48700898ac39b754505c633 | c1ccc(-c2n[nH]cc2-c2ccncn2)cc1 | C-N(-C)/[CH;D2;+0:1]=[C;H0;D3;+0:2](/[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8])-[c;H0;D3;+0:9]1:[#7;a:10]:[c:11](-[Cl;D1;H0:12]):[#7;a:13]:[c:14]:[c:15]:1.[NH2;D1;+0:16]-[NH2;D1;+0:17]>>[Cl;D1;H0:12]-[c:11]1:[#7;a:13]:[c:14]:[c:15]:[c;H0;D3;+0:9](-[c;H0;D3;+0:2]2:[cH;D2;+0:1]:[nH;D2;+0:17]:[n;H0;D2;+0... | 48.1 | [{"value": 48.1, "product": "ClC1=NC=CC(=N1)C=1C(=NNC1)C1=CC=C(C=C1)F", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | null | null | A solution of the compound prepared in step 3 (4.4 g) and hydrazine hydrate (0.82 g, 0.014 mol) was stirred at room temperature for 6 hours. The yellow precipitate was collected by filtration and air-dried to give 1.85 g of 2-chloro-4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]pyrimidine as a yellow solid, mp: 204-205° C.; An... | 10.6084/m9.figshare.5104873.v1 | null | Enamine.Hydrazine.Ketone | null | null | c1cn[nH]c1 | c1ccccc1.c1cn[nH]c1.c1cncnc1 | HO- | null | null | null | CN(C)/C=C(/C(=O)c1ccc(F)cc1)c1ccnc(Cl)n1.NN>>Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-507202d3eb7145aca8d59b99a4f65adf | CN.Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1>>CNc1nccc(-c2c[nH]nc2-c2ccc(F)cc2)n1 | ClC1=NC=CC(=N1)C=1C(=NNC1)C1=CC=C(C=C1)F.CN>>FC1=CC=C(C=C1)C1=NNC=C1C1=NC(=NC=C1)NC | [CH3:1][NH2:2].Cl[c:3]1[n:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][nH:10][n:11][c:12]2-[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[n:20]1>>[CH3:1][NH:2][c:3]1[n:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][nH:10][n:11][c:12]2-[c:13]2[cH:14][cH:15][c:16]([F:17])[cH:18][cH:19]2)[n:20]1 | CN.Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1 | CNc1nccc(-c2c[nH]nc2-c2ccc(F)cc2)n1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2n[nH]cc2-c2ccncn2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[C;D1;H3:6]-[NH2;D1;+0:7]>>[C;D1;H3:6]-[NH;D2;+0:7]-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5] | null | [] | 100 | CELSIUS | null | null | A suspension of 2-chloro-4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]pyrimidine prepared in accordance with Example A-299 (0.3 g, 0.0011 mol) in 10 mL of methylamine (40% water solution) was heated in a sealed tube at 100° C. overnight. The mixture was then cooled to room temperature and the precipitate was filtered, air-dri... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1cncnc1.c1cn[nH]c1.c1ccccc1 | HCl | null | 100 | null | CN.Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1>>CNc1nccc(-c2c[nH]nc2-c2ccc(F)cc2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-47778ad10aac4ff2a711d212a18b5a25 | Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1>>Fc1ccc(-c2n[nH]cc2-c2ccnc(NCc3ccccc3)n2)cc1 | ClC1=NC=CC(=N1)C=1C(=NNC1)C1=CC=C(C=C1)F>>FC1=CC=C(C=C1)C1=NNC=C1C1=NC(=NC=C1)NCC1=CC=CC=C1 | Cl[c:15]1[n:14][cH:13][cH:12][c:11](-[c:10]2[c:6](-[c:5]3[cH:4][cH:3][c:2]([F:1])[cH:26][cH:17]3)[n:7][nH:8][cH:9]2)[n:16]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][nH:8][cH:9][c:10]2-[c:11]2[cH:12][cH:13][n:14][c:15]([NH:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[n:24]2)[cH:25][cH:26]1 | Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1 | Fc1ccc(-c2n[nH]cc2-c2ccnc(NCc3ccccc3)n2)cc1 | null | null | C(C1=CC=CC=C1)N | Aromatic Heterocycle Formation | OtherReaction | f414cdc2ebd114672a29511220b1d1b701c7a5d7e3abef7f1fd791da8adc5b0d | b0f572ad6b2b446ecd070d99ad48b6b5e87dc037ba48cc85596343bac1b77f42 | c1ccc(CNc2nccc(-c3c[nH]nc3-c3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[c:4]:[c;H0;D3;+0:5](-[c:6]2:[c:7]:[#7;a:8]:[#7;a:9]:[c:10]:2-[c;H0;D3;+0:11]2:[c:12]:[c:13]:[c:14](-[F;D1;H0:15]):[cH;D2;+0:16]:[cH;D2;+0:17]:2):[n;H0;D2;+0:18]:1>>[F;D1;H0:15]-[c:14]1:[c:13]:[c:12]:[c;H0;D3;+0:11](-[c:10]2:[#7;a:9]:[#7;a:8]:[c:7]:[c:6]:2-[c;H0;D3;+0:5]2:[#7;a:19]:[c;... | 95 | [{"value": 95.0, "product": "FC1=CC=C(C=C1)C1=NNC=C1C1=NC(=NC=C1)NCC1=CC=CC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was synthesize by refluxing 2-chloro-4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]pyrimidine prepared in accordance with Example A-299 in benzylamine overnight. The product, 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-N-(phenylmethyl)-2-pyrimidinamine, was obtained as a white solid in 95% yield; mp: 216-217° C.; Anal... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide | Secondary amine | c1cncnc1.c1ccccc1 | c1ccccc1.c1cncnc1.c1ccccc1 | c1ccccc1.c1cn[nH]c1.c1cncnc1.c1ccccc1 | null | C(C1=CC=CC=C1)N | null | null | Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1>C(C1=CC=CC=C1)N>Fc1ccc(-c2n[nH]cc2-c2ccnc(NCc3ccccc3)n2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-3eacffbe941e42079c0771b9a848e2a1 | Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1.NC1CC1>>Fc1ccc(-c2n[nH]cc2-c2ccnc(NC3CC3)n2)cc1 | ClC1=NC=CC(=N1)C=1C(=NNC1)C1=CC=C(C=C1)F.C1(CC1)N>>C1(CC1)NC1=NC=CC(=N1)C=1C(=NNC1)C1=CC=C(C=C1)F | Cl[c:15]1[n:14][cH:13][cH:12][c:11](-[c:10]2[c:6](-[c:5]3[cH:4][cH:3][c:2]([F:1])[cH:22][cH:21]3)[n:7][nH:8][cH:9]2)[n:20]1.[NH2:16][CH:17]1[CH2:18][CH2:19]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][nH:8][cH:9][c:10]2-[c:11]2[cH:12][cH:13][n:14][c:15]([NH:16][CH:17]3[CH2:18][CH2:19]3)[n:20]2)[cH:21][cH:22]1 | Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1.NC1CC1 | Fc1ccc(-c2n[nH]cc2-c2ccnc(NC3CC3)n2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(-c2n[nH]cc2-c2ccnc(NC3CC3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[C:7]1-[C:8]-[C:9]-1>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]1-[C:8]-[C:9]-1):[#7;a:2]:[c:3] | 26 | [{"value": 26.0, "product": "C1(CC1)NC1=NC=CC(=N1)C=1C(=NNC1)C1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was synthesized by stirring 2-chloro-4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]pyrimidine prepared in accordance with Example A-299 with excess cyclopropylamine in methanol at 50° C. for 12 hours. The product, N-cyclopropyl-4-(3-(4-fluorophenyl)-1H-pyrazol-4-yl)-2-pyrimidinamine, was obtained as a white solid... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cn[nH]c1.c1cncnc1.C1CC1 | HCl | CO | null | null | Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1.NC1CC1>CO>Fc1ccc(-c2n[nH]cc2-c2ccnc(NC3CC3)n2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-7ad8c779d296451c9fe0a61f950921a6 | COc1ccc(CN)cc1.Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1>>COc1ccc(CNc2nccc(-c3c[nH]nc3-c3ccc(F)cc3)n2)cc1 | ClC1=NC=CC(=N1)C=1C(=NNC1)C1=CC=C(C=C1)F.COC1=CC=C(CN)C=C1>>FC1=CC=C(C=C1)C1=NNC=C1C1=NC(=NC=C1)NCC1=CC=C(C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH2:8])[cH:27][cH:28]1.Cl[c:9]1[n:10][cH:11][cH:12][c:13](-[c:14]2[cH:15][nH:16][n:17][c:18]2-[c:19]2[cH:20][cH:21][c:22]([F:23])[cH:24][cH:25]2)[n:26]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][NH:8][c:9]2[n:10][cH:11][cH:12][c:13](-[c:14]3[cH:15][nH:16][n:17][c:18]3-[c:1... | COc1ccc(CN)cc1.Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1 | COc1ccc(CNc2nccc(-c3c[nH]nc3-c3ccc(F)cc3)n2)cc1 | null | null | null | Heteroatom Alkylation and Arylation | N-arylation (Buchwald-Hartwig/Ullmann-Goldberg) | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(CNc2nccc(-c3c[nH]nc3-c3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[C:7]-[c:8]>>[c:3]:[#7;a:2]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[C:7]-[c:8]):[#7;a:4]:[c:5] | 80 | [{"value": 80.0, "product": "FC1=CC=C(C=C1)C1=NNC=C1C1=NC(=NC=C1)NCC1=CC=C(C=C1)OC", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | This compound was synthesized by refluxing 2-chloro-4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]pyrimidine prepared in accordance with Example A-299 in 4-methoxybenzylamine overnight. The product, 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-N-[(4-methoxyphenyl)methyl]-2-pyrimidinamine, was obtained as a off-white solid in 80% yie... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cncnc1.c1cn[nH]c1.c1ccccc1 | HCl | null | null | null | COc1ccc(CN)cc1.Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1>>COc1ccc(CNc2nccc(-c3c[nH]nc3-c3ccc(F)cc3)n2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8a35d8e72a834eba9ed520931875ceb5 | CC(=O)OC(C)=O.Fc1ccc(-c2n[nH]cc2-c2ccnc(NCc3ccccc3)n2)cc1>>CC(=O)N(Cc1ccccc1)c1nccc(-c2c[nH]nc2-c2ccc(F)cc2)n1 | FC1=CC=C(C=C1)C1=NNC=C1C1=NC(=NC=C1)NCC1=CC=CC=C1.C(C)(=O)OC(C)=O.C(C)N(CC)CC>>FC1=CC=C(C=C1)C1=NNC=C1C1=NC(=NC=C1)N(C(C)=O)CC1=CC=CC=C1 | CC(=O)O[C:2]([CH3:1])=[O:3].[NH:4]([CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[n:13][cH:14][cH:15][c:16](-[c:17]2[cH:18][nH:19][n:20][c:21]2-[c:22]2[cH:23][cH:24][c:25]([F:26])[cH:27][cH:28]2)[n:29]1>>[CH3:1][C:2](=[O:3])[N:4]([CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[n:13][cH:14][cH:15][c:16](-... | CC(=O)OC(C)=O.Fc1ccc(-c2n[nH]cc2-c2ccnc(NCc3ccccc3)n2)cc1 | CC(=O)N(Cc1ccccc1)c1nccc(-c2c[nH]nc2-c2ccc(F)cc2)n1 | null | CN(C)C=1C=CN=CC1 | C1CCOC1 | Acylation | Aminolysis of esters | 72a6d1966b6b15ac7195d4682af251dc9ffac857f784a4242970ab5c7a529369 | 6593c6062585994f02076cd3c86920ae7244b86659eab65c21b5a8628c6d4bb8 | c1ccc(CNc2nccc(-c3c[nH]nc3-c3ccccc3)n2)cc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[c:4]:[#7;a:5]:[c:6](-[NH;D2;+0:7]-[C:8]-[c:9]):[#7;a:10]:[c:11]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:7](-[C:8]-[c:9])-[c:6](:[#7;a:5]:[c:4]):[#7;a:10]:[c:11] | null | [] | null | null | 8 | HOUR | To a mixture of 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-N-(phenylmethyl)-2-pyrimidinamine prepared in accordance with Example A-303 (0.15 g, 0.00043 mol), DMAP (0.027 g, 0.00022 mol) and acetic anhydride (0.066 g, 0.00066 mol) in 10 mL of THF was added triethylamine (0.053 g, 0.00052 mol). The solution was stirred at ro... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amine | Tertiary amide | null | null | c1ccccc1.c1cncnc1.c1cn[nH]c1.c1ccccc1 | HO- | CN(C)C=1C=CN=CC1.C1CCOC1 | null | 8 | CC(=O)OC(C)=O.Fc1ccc(-c2n[nH]cc2-c2ccnc(NCc3ccccc3)n2)cc1>CN(C)C=1C=CN=CC1.C1CCOC1>CC(=O)N(Cc1ccccc1)c1nccc(-c2c[nH]nc2-c2ccc(F)cc2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-332c3dbc1271454ab55d4fb27ca04f5b | CCOC(=O)Cl.Nc1nccc(-c2c[nH]nc2-c2ccc(F)cc2)n1>>CCOC(=O)Nc1nccc(-c2c[nH]nc2-c2ccc(F)cc2)n1 | O.FC1=CC=C(C=C1)C1=NNC=C1C1=NC(=NC=C1)N.C1=CN=C(N=C1)NS(=O)(=O)C2=CC=C(C=C2)N.ClC(=O)OCC>>C(C)OC(NC1=NC=CC(=N1)C=1C(=NNC1)C1=CC=C(C=C1)F)=O | Cl[C:4]([O:3][CH2:2][CH3:1])=[O:5].[NH2:6][c:7]1[n:8][cH:9][cH:10][c:11](-[c:12]2[cH:13][nH:14][n:15][c:16]2-[c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]2)[n:24]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[NH:6][c:7]1[n:8][cH:9][cH:10][c:11](-[c:12]2[cH:13][nH:14][n:15][c:16]2-[c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][cH:... | CCOC(=O)Cl.Nc1nccc(-c2c[nH]nc2-c2ccc(F)cc2)n1 | CCOC(=O)Nc1nccc(-c2c[nH]nc2-c2ccc(F)cc2)n1 | null | null | N1=CC=CC=C1 | Protection | Acylation of Nitrogen Nucleophiles by Acyl/Thioacyl/Carbamoyl Halides and Analogs_OS | 038720aa61a7efa0f2a9ee6f2e0adf63a9ffdc2be4697c11a6215baef34f97b2 | 205f353513ce9506ab61831799da8fb73ec2ef5cfa927664496d3ce72c438860 | c1ccc(-c2n[nH]cc2-c2ccncn2)cc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4].[NH2;D1;+0:5]-[c:6](:[#7;a:7]:[c:8]):[#7;a:9]:[c:10]>>[C:4]-[#8:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[c:6](:[#7;a:7]:[c:8]):[#7;a:9]:[c:10] | null | [] | null | null | 6 | HOUR | To a suspension of 4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]-2-pyrimidinamine prepared in accordance with Example A-306 (0.26 g, 0.001 mol) in 5 mL of pyridine was added ethyl chloroformate dropwise. After the addition, the clear solution was stirred at room temperature for 6 hours. Water was added and the aqueous phase w... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ether.Primary amine | Carbamic ester | null | null | c1cncnc1.c1cn[nH]c1.c1ccccc1 | HCl | N1=CC=CC=C1 | null | 6 | CCOC(=O)Cl.Nc1nccc(-c2c[nH]nc2-c2ccc(F)cc2)n1>N1=CC=CC=C1>CCOC(=O)Nc1nccc(-c2c[nH]nc2-c2ccc(F)cc2)n1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-f063ce1a31b14145937e680188c797d5 | CC[C@H](C)[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](C)NC(=O)[C@H](C)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)C(C)C)C(C)C.COC(=O)c1cccc(C)c1.Cc1ccncn1.O=C(Cc1ccncc1)c1ccc(F)cc1>>Cc1cccc(-c2n[nH]cc2-c2ccncn2)c1 | CC=1C=C(C(=O)OC)C=CC1.CC[C@H](C)[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](C)NC(=O)[C@H](C)N.FC1=CC=C(C(=O)CC2=CC=NC=C2)C=C1.CC1=NC=NC=C1>>CC=1C=C(C=CC1)C1=NNC=C1C1=NC=NC=C1 | CC[C@H](C)[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](C)NC(=O)[C@H](C)N)C(=O)N[C@@H](CCCCN)C(=O)[NH:8][C@H](C(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)C(C)C)C(C)C.CO[C:7](=O)[c:6]1[cH:5][cH:4][cH:3][c:2]([CH3:1])[cH:18]1.[CH3:11][c:12]1[cH:13][cH:14][n:15][cH:16][... | CC[C@H](C)[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](C)NC(=O)[C@H](C)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)C(C)C)C(C)C.COC(=O)c1cccc(C)c1.Cc1ccncn1.O=C(Cc1ccncc1)c1ccc(F)cc1 | Cc1cccc(-c2n[nH]cc2-c2ccncn2)c1 | null | null | null | Miscellaneous | OtherReaction | 5d185fa330956694446a5ce13c104e9c2fe8d95e6592b182417951877b53016a | 8fd360cfe649c09aa9c4ca06ea883331a0800bec68f3cb05a1b6221ccce33e79 | c1ccc(-c2n[nH]cc2-c2ccncn2)cc1 | C-C-[C@H](-C)-[C@H](-N-C(=O)-[C@H](-C-O)-N-C(=O)-[C@H](-C)-N-C(=O)-[C@H](-C)-N)-C(=O)-N-[C@@H](-C-C-C-C-N)-C(=O)-[NH;D2;+0:1]-[C@H](-C(-C)-C)-C(=O)-N-[C@@H](-C)-C(=O)-N-[C@H](-C(-C)-C)-C(=O)-N-[C@@H](-C-O)-C(=O)-N-[C@@H](-C)-C(=O)-N-[C@@H](-C-C(-O)=O)-C(=O)-N-[C@@H](-C-C-C-N=C(-N)-N)-C(-O)=O.C-O-[C;H0;D3;+0:2](=O)-[c;H... | null | [] | null | null | null | null | This compound was prepared by the same procedure as described for Example A-208 except that 1-methyl-3-(4′-pyrimidinylacetyl) benzene (prepared as set forth in Step 1 of Example A-19 from 4-methyl-pyrimidine and methyl 3-methylbenzoate) was used in place of 4-fluorobenzoyl-4-pyridinyl methane.
Conditions: See reaction.... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Carboxylic acid.Carboxylic acid.Ketone.Ester.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Secondary amide.Primary alcohol.Primary alcohol.Primary amine.Primary amine.Primary amine.Primary a... | null | c1ccncc1.c1ccccc1 | c1cn[nH]c1 | c1ccccc1.c1cn[nH]c1.c1cncnc1 | HF | null | null | null | CC[C@H](C)[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](C)NC(=O)[C@H](C)N)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)C(C)C)C(C)C.COC(=O)c1cccc(C)c1.Cc1ccncn1.O=C(Cc1ccncc1)c1ccc(F)cc1>>Cc1cccc(-c2n[nH]cc2-c2ccncn2)c1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-29ac42e35fb54511a6e1cdaf8ed77d68 | Cc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1.[O]=[Mn](=[O])(=[O])[O-]>>O=C(O)c1n[nH]c(-c2ccc(F)cc2)c1-c1ccncc1 | O.FC1=CC=C(C=C1)C1=NNC(=C1C1=CC=NC=C1)C.[Mn](=O)(=O)(=O)[O-].[K+].[Mn](=O)(=O)(=O)[O-].[K+]>>O.FC1=CC=C(C=C1)C1=C(C(=NN1)C(=O)O)C1=CC=NC=C1 | [CH3:3][c:5]1[nH:6][n:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]2)[c:16]1-[c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1.[O]=[Mn](=[O])(=[O:2])[O-:4]>>[O:2]=[C:3]([OH:4])[c:5]1[n:6][nH:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([F:13])[cH:14][cH:15]2)[c:16]1-[c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1 | Cc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1.[O]=[Mn](=[O])(=[O])[O-] | O=C(O)c1n[nH]c(-c2ccc(F)cc2)c1-c1ccncc1 | null | null | C(C)(C)(C)O | Acylation | OtherReaction | 7769a4cd09a67e270ac2d1d32df6b7a59b468ff590f9c59723b72ba3c8deb342 | 903e48d04e4504a4fe6977f5e5582144adff237d0488a4542a1907161cf0134c | c1ccc(-c2[nH]ncc2-c2ccncc2)cc1 | [CH3;D1;+0:1]-[c:2]1:[c:3]:[c:4](-[c:5]):[n;H0;D2;+0:6]:[nH;D2;+0:7]:1.[O-;H0;D1:8]-[Mn](=[O;H0;D1;+0:9])(=[O])=[O]>>[O;H0;D1;+0:9]=[C;H0;D3;+0:1](-[OH;D1;+0:8])-[c:2]1:[c:3]:[c:4](-[c:5]):[nH;D2;+0:6]:[n;H0;D2;+0:7]:1 | 40.6 | [{"value": 40.6, "product": "O.FC1=CC=C(C=C1)C1=C(C(=NN1)C(=O)O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 8 | HOUR | A mixture of 4-[3-(4-fluorophenyl)-5-methyl-1H-pyrazol-4-yl)pyridine (5.8 g, 24.0909 mmol; prepared as set forth in Example A-4) and potassium permanganate (7.6916 g, 48.1818 mmol) in water (7.5 mL) and tert-butanol (10 mL) was heated to reflux at 95 to 100° C. for 6 hours (or until all the potassium permanganate was c... | 10.6084/m9.figshare.5104873.v1 | null | null | Carboxylic acid | null | null | c1cn[nH]c1.c1ccccc1.c1ccncc1 | HO- | C(C)(C)(C)O | null | 8 | Cc1[nH]nc(-c2ccc(F)cc2)c1-c1ccncc1.[O]=[Mn](=[O])(=[O])[O-]>C(C)(C)(C)O>O=C(O)c1n[nH]c(-c2ccc(F)cc2)c1-c1ccncc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-48d632ca4e0f40deb2677fcf9e2654d8 | CC(C)(C)OC(=O)N1CCN(C(=O)c2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1>>CN1CCN(Cc2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1 | FC1=CC=C(C=C1)C1=C(C(=NN1)C(=O)N1CCN(CC1)C(=O)OC(C)(C)C)C1=CC=NC=C1.[OH-].[K+].CO.C(C)(=O)OCC.[NH4+].[OH-]>>FC1=CC=C(C=C1)C1=C(C(=NN1)CN1CCN(CC1)C)C1=CC=NC=C1 | CC(C)(C)O[C:1](=O)[N:2]1[CH2:3][CH2:4][N:5]([C:6](=O)[c:7]2[n:8][nH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]3)[c:18]2-[c:19]2[cH:20][cH:21][n:22][cH:23][cH:24]2)[CH2:25][CH2:26]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH2:6][c:7]2[n:8][nH:9][c:10](-[c:11]3[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]3)[c:18... | CC(C)(C)OC(=O)N1CCN(C(=O)c2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1 | CN1CCN(Cc2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1 | null | null | O1CCCC1.O.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(C)(=O)OCC | Reduction | OtherReaction | d1e38ff76373f2f85a70c476a5d7ea2d461bd8feff67e57b568219071b445e34 | e3e848d08b64607479a3af6f757302d1c3f585ca2558bd4bfb2ce28c641ade14 | c1ccc(-c2[nH]nc(CN3CCNCC3)c2-c2ccncc2)cc1 | C-C(-C)(-C)-O-[C;H0;D3;+0:1](=O)-[#7:2]1-[C:3]-[C:4]-[#7:5](-[C;H0;D3;+0:6](=O)-[c:7]2:[#7;a:8]:[#7;a:9]:[c:10]:[c:11]:2)-[C:12]-[C:13]-1>>[CH3;D1;+0:1]-[#7:2]1-[C:3]-[C:4]-[#7:5](-[CH2;D2;+0:6]-[c:7]2:[#7;a:8]:[#7;a:9]:[c:10]:[c:11]:2)-[C:12]-[C:13]-1 | 50.1 | [{"value": 50.1, "product": "FC1=CC=C(C=C1)C1=C(C(=NN1)CN1CCN(CC1)C)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}, {"value": 43.0, "product": "FC1=CC=C(C=C1)C1=C(C(=NN1)CN1CCN(CC1)C)C1=CC=NC=C1", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 1.5 | HOUR | To a suspension of 1,1-dimethylethyl 4-[[5-(4-fluorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]carbonyl]-1-piperazinecarboxylate (0.451 g, 1.0 mL) in dry tetrahydrofuran (8 mL), 1.0N LiAlH4 in tetrahydrofuran (2.5 mL, 2.5 mmol) was added dropwise at such a rate as to maintain reflux over 15 minutes. Upon the addition, the... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Tertiary amide.Boc | null | null | null | C1C[NH]CC[NH]1.c1cn[nH]c1.c1ccccc1.c1ccncc1 | HO- | O1CCCC1.O.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(C)(=O)OCC | null | 1.5 | CC(C)(C)OC(=O)N1CCN(C(=O)c2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1>O1CCCC1.O.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(C)(=O)OCC>CN1CCN(Cc2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-78ee5e4781a84148947e6b81bd1b4bd5 | CCOC(=O)CC1CCN(C(=O)OC(C)(C)C)CC1.Cc1ccncc1>>CC(C)(C)OC(=O)N1CCC(CC(=O)Cc2ccncc2)CC1 | [Cl-].[Ce+3].[Cl-].[Cl-].C(C)(C)[N-]C(C)C.C(CCC)[Li].CCCCCC.N1=CC=C(C=C1)C.C(C)(C)[N-]C(C)C.[Li+].C(C)(C)[N-]C(C)C.[Li+].CC(C)(OC(=O)N1CCC(CC1)CC(=O)OCC)C>>O=C(CC1CCN(CC1)C(=O)OC(C)(C)C)CC1=CC=NC=C1 | CCO[C:13]([CH2:12][CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:23][CH2:22]1)=[O:14].[CH3:15][c:16]1[cH:17][cH:18][n:19][cH:20][cH:21]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][C:13](=[O:14])[CH2:15][c:16]2[cH:17][cH:18][n:19][cH:20][cH:... | CCOC(=O)CC1CCN(C(=O)OC(C)(C)C)CC1.Cc1ccncc1 | CC(C)(C)OC(=O)N1CCC(CC(=O)Cc2ccncc2)CC1 | null | null | C(C)(=O)OCC.CCCCCC.O1CCCC1 | C-C Coupling | OtherReaction | 8ce89878f5db9b98fa4633d16adf2407dbf79d96925d930c608f1ce0756e674e | f80cbbd7f2bfc042e62829b7de30498cf0880b808f2adad888ffdfe089982722 | O=C(Cc1ccncc1)CC1CCNCC1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C:4].[CH3;D1;+0:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1>>[C:4]-[C:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[CH2;D2;+0:5]-[c:6]1:[c:7]:[c:8]:[#7;a:9]:[c:10]:[c:11]:1 | 25 | [{"value": 25.0, "product": "O=C(CC1CCN(CC1)C(=O)OC(C)(C)C)CC1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | -78 | CELSIUS | 1.5 | HOUR | To a solution of diisopropylamide (6.15 mL, 43.91 mmol) in dry tetrahydrofuran (40 mL) at 0° C. was added 2.5 M butyl lithium solution in hexane (16.22 mL, 40.53 mmol) dropwise over 10 minutes. After the addition, the lithium diisopropylamide solution was stirred at 0° C. for 20 minutes, then cooled to −78° C. 4-Picoli... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Ketone | null | null | C1CC[NH]CC1.c1ccncc1 | HO- | C(C)(=O)OCC.CCCCCC.O1CCCC1 | -78 | 1.5 | CCOC(=O)CC1CCN(C(=O)OC(C)(C)C)CC1.Cc1ccncc1>C(C)(=O)OCC.CCCCCC.O1CCCC1>CC(C)(C)OC(=O)N1CCC(CC(=O)Cc2ccncc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-2004ca65deec472ebfed350e5c6220a7 | CC(C)(C)OC(=O)N1CCC(CC(=O)Cc2ccncc2)CC1.O=Cc1ccc(F)cc1>>CC(C)(C)OC(=O)N1CCC(CC(=O)C(=Cc2ccc(F)cc2)c2ccncc2)CC1 | FC1=CC=C(C=O)C=C1.N1=CC=C(C=C1)CC(C)=O.FC=1C=C(C=O)C=CC1OC.O=C(CC1CCN(CC1)C(=O)OC(C)(C)C)CC1=CC=NC=C1>>FC1=CC=C(C=C1)C=C(C(CC1CCN(CC1)C(=O)OC(C)(C)C)=O)C1=CC=NC=C1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][C:13](=[O:14])[CH2:15][c:24]2[cH:25][cH:26][n:27][cH:28][cH:29]2)[CH2:30][CH2:31]1.O=[CH:16][c:17]1[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][C:13... | CC(C)(C)OC(=O)N1CCC(CC(=O)Cc2ccncc2)CC1.O=Cc1ccc(F)cc1 | CC(C)(C)OC(=O)N1CCC(CC(=O)C(=Cc2ccc(F)cc2)c2ccncc2)CC1 | null | null | null | C-C Coupling | Aldol condensation | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(CC1CCNCC1)C(=Cc1ccccc1)c1ccncc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](=[O;D1;H0:7])-[CH2;D2;+0:8]-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1>>[C:5]-[C:6](=[O;D1;H0:7])-[C;H0;D3;+0:8](=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4])-[c:9]1:[c:10]:[c:11]:[#7;a:12]:[c:13]:[c:14]:1 | null | [] | null | null | null | null | 1,1-Dimethylethyl 4-[4-(4-fluorophenyl)-2-oxo-3-(4-pyridinyl)-3-butenyl]-1-piperidinecarboxylate was prepared by the same method as described for step 1 of Example A-1 by replacing 4-pyridylacetone and 3-fluoro-p-anisaldehyde with the ketone of step 2 of the present Example and 4-fluorobenzaldehyde, respectively.
Condi... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | C1CC[NH]CC1.c1ccccc1.c1ccncc1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(CC(=O)Cc2ccncc2)CC1.O=Cc1ccc(F)cc1>>CC(C)(C)OC(=O)N1CCC(CC(=O)C(=Cc2ccc(F)cc2)c2ccncc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-e777a6ab67484a6788036952d7e3878b | CC(=O)C(=Cc1ccccc1)c1ccncc1.CC(C)(C)OC(=O)N1CCC(CC(=O)C(=Cc2ccc(F)cc2)c2ccncc2)CC1>>CC(C)(C)OC(=O)N1CCC(CC(=O)C2(c3ccncc3)OC2c2ccc(F)cc2)CC1 | C1(=CC=CC=C1)C=C(C(C)=O)C1=CC=NC=C1.FC1=CC=C(C=C1)C=C(C(CC1CCN(CC1)C(=O)OC(C)(C)C)=O)C1=CC=NC=C1>>FC1=CC=C(C=C1)C1C(O1)(C1=CC=NC=C1)C(CC1CCN(CC1)C(=O)OC(C)(C)C)=O | CC(C(=Cc1ccccc1)c1ccncc1)=[O:22].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH:11]([CH2:12][C:13](=[O:14])[C:15]([c:16]2[cH:17][cH:18][n:19][cH:20][cH:21]2)=[CH:23][c:24]2[cH:25][cH:26][c:27]([F:28])[cH:29][cH:30]2)[CH2:31][CH2:32]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:... | CC(=O)C(=Cc1ccccc1)c1ccncc1.CC(C)(C)OC(=O)N1CCC(CC(=O)C(=Cc2ccc(F)cc2)c2ccncc2)CC1 | CC(C)(C)OC(=O)N1CCC(CC(=O)C2(c3ccncc3)OC2c2ccc(F)cc2)CC1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 24e5a88ce69d7c2c82159f3a967c4e67572dd01e387f05153ff2a48694ec7bd7 | ab6b65f5e9f2eb3ba4b4737f10d104b1ae24afb168129247d60e743fa5ac8b83 | O=C(CC1CCNCC1)C1(c2ccncc2)OC1c1ccccc1 | C-C(=[O;H0;D1;+0:1])-C(=C-c1:c:c:c:c:c:1)-c1:c:c:n:c:c:1.[C:2]-[C:3](=[O;D1;H0:4])-[C;H0;D3;+0:5](=[CH;D2;+0:6]-[c:7](:[c:8]):[c:9])-[c:10]1:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:1>>[C:2]-[C:3](=[O;D1;H0:4])-[C;H0;D4;+0:5]1(-[c:10]2:[c:11]:[c:12]:[#7;a:13]:[c:14]:[c:15]:2)-[O;H0;D2;+0:1]-[CH;D3;+0:6]-1-[c:7](:[c:8]):[c... | null | [] | null | null | null | null | 1,1-Dimethylethyl 4-(2-[3-(4-fluorophenyl)-2-(4-pyridinyl)oxiranyl]-2-oxoethyl]-1-piperidinecarboxylate was prepared by the same method as described for step 3 of Example A-2 by replacing 4-phenyl-3-(4-pyridyl)-3-butene-2-one with the α,β unsaturated ketone of step 3 of the present Example.
Conditions: See reaction.not... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ketone | Ketone.Ether | c1ccccc1.c1ccncc1 | C1CO1 | C1CC[NH]CC1.c1ccncc1.C1CO1.c1ccccc1 | Other | null | null | null | CC(=O)C(=Cc1ccccc1)c1ccncc1.CC(C)(C)OC(=O)N1CCC(CC(=O)C(=Cc2ccc(F)cc2)c2ccncc2)CC1>>CC(C)(C)OC(=O)N1CCC(CC(=O)C2(c3ccncc3)OC2c2ccc(F)cc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-d11da7ec693843858f9cb323ee94d22b | CC(C)(C)OC(=O)N1CCC(CC(=O)C2(c3ccncc3)OC2c2ccc(F)cc2)CC1.NN>>CC(C)(C)OC(=O)N1CCC(CC2=NNC(c3ccc(F)cc3)C2(O)c2ccncc2)CC1 | FC1=CC=C(C=C1)C1C(O1)(C1=CC=NC=C1)C(CC1CCN(CC1)C(=O)OC(C)(C)C)=O.NN>>FC1=CC=C(C=C1)C1C(C(=NN1)CC1CCN(CC1)C(=O)OC(C)(C)C)(C1=CC=NC=C1)O | O=[C:13]([CH2:12][CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:33][CH2:32]1)[C:24]1([c:26]2[cH:27][cH:28][n:29][cH:30][cH:31]2)[CH:16]([c:17]2[cH:18][cH:19][c:20]([F:21])[cH:22][cH:23]2)[O:25]1.[NH2:14][NH2:15]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C... | CC(C)(C)OC(=O)N1CCC(CC(=O)C2(c3ccncc3)OC2c2ccc(F)cc2)CC1.NN | CC(C)(C)OC(=O)N1CCC(CC2=NNC(c3ccc(F)cc3)C2(O)c2ccncc2)CC1 | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 413aebc198e33af37de46cc9dc029a0a6e192f19d16a03f65d960d12511c5bf0 | 58e6d8eaf186f1d0e9a62408070dce07b35e7010855b0bf338cff7a37f228f81 | c1ccc(C2NN=C(CC3CCNCC3)C2c2ccncc2)cc1 | O=[C;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]1(-[c:5])-[O;H0;D2;+0:6]-[CH;D3;+0:7]-1-[c:8](:[c:9]):[c:10].[NH2;D1;+0:11]-[NH2;D1;+0:12]>>[C:3]-[C:2]-[C;H0;D3;+0:1]1=[N;H0;D2;+0:11]-[NH;D2;+0:12]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[C:4]-1(-[OH;D1;+0:6])-[c:5] | 53.9 | [{"value": 53.9, "product": "FC1=CC=C(C=C1)C1C(C(=NN1)CC1CCN(CC1)C(=O)OC(C)(C)C)(C1=CC=NC=C1)O", "details": "PERCENTYIELD", "is_desired": false}] | null | null | null | null | To a solution of 1,1-dimethylethyl 4-[2-[3-(4-fluorophenyl)-2-(4-pyridinyl)oxiranyl]-2-oxoethyl]-1-piperidinecarboxylate prepared in step 4 of this Example (3.45 g, 7.8409 mmol) in ethanol (15 mL), anhydrous hydrazine (0.50 mL, 15.6818 mmol) was added. The reaction was heated to reflux overnight. The reaction solution ... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ether | Hydrazone.Tertiary alcohol | C1CO1 | C1=NNCC1 | C1CC[NH]CC1.C1=NNCC1.c1ccccc1.c1ccncc1 | HO- | C(C)O | null | null | CC(C)(C)OC(=O)N1CCC(CC(=O)C2(c3ccncc3)OC2c2ccc(F)cc2)CC1.NN>C(C)O>CC(C)(C)OC(=O)N1CCC(CC2=NNC(c3ccc(F)cc3)C2(O)c2ccncc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-16d796de8c3d43a5b96bf661f394c01e | CC(C)(C)OC(=O)N1CCC(Cc2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1>>Fc1ccc(-c2n[nH]c(CC3CCNCC3)c2-c2ccncc2)cc1 | O.FC1=CC=C(C=C1)C1=C(C(=NN1)C(=O)N1CCNCC1)C1=CC=NC=C1.FC1=CC=C(C=C1)C1=C(C(=NN1)CC1CCN(CC1)C(=O)OC(C)(C)C)C1=CC=NC=C1>>FC1=CC=C(C=C1)C1=NNC(=C1C1=CC=NC=C1)CC1CCNCC1 | CC(C)(C)OC(=O)[N:14]1[CH2:13][CH2:12][CH:11]([CH2:10][c:9]2[n:8][nH:7][c:6](-[c:5]3[cH:4][cH:3][c:2]([F:1])[cH:25][cH:24]3)[c:17]2-[c:18]2[cH:19][cH:20][n:21][cH:22][cH:23]2)[CH2:16][CH2:15]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][nH:8][c:9]([CH2:10][CH:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]3)[c:17]2-[c:18]2[c... | CC(C)(C)OC(=O)N1CCC(Cc2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1 | Fc1ccc(-c2n[nH]c(CC3CCNCC3)c2-c2ccncc2)cc1 | null | null | null | Reduction | OtherReaction | bf3cd5dc3e17e694d8665c89f5d7e08e8763b18436a633eb66e9bf530b8b0316 | a94b29c7264c852156fc1cdd4a0951a4fc26c06d0edc9e50c743825dbf79e3fd | c1ccc(-c2n[nH]c(CC3CCNCC3)c2-c2ccncc2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2]-[C:3])-[C:4]-[C:5].[C:6]-[c:7]1:[c:8]:[c:9](-[c:10]):[nH;D2;+0:11]:[n;H0;D2;+0:12]:1>>[C:3]-[C:2]-[NH;D2;+0:1]-[C:4]-[C:5].[C:6]-[c:7]1:[c:8]:[c:9](-[c:10]):[n;H0;D2;+0:11]:[nH;D2;+0:12]:1 | null | [] | null | null | null | null | 4-[3-(4-Fluorophenyl)-5-(4-piperidinylmethyl)-1H-pyrazol-4-yl]pyridine was prepared using the same method as described for Example A-314, step 1 by replacing 1-[[5-(4-fluorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]carbonyl]piperazine, monohydrate with the pyrazole of step 5 of the present Example. Anal. Calc'd for C20H2... | 10.6084/m9.figshare.5104873.v1 | null | Carbamic ester.Ether.Boc | Secondary amine | C1CC[NH]CC1 | C1CCNCC1 | c1ccccc1.c1cn[nH]c1.C1CCNCC1.c1ccncc1 | HO- | null | null | null | CC(C)(C)OC(=O)N1CCC(Cc2n[nH]c(-c3ccc(F)cc3)c2-c2ccncc2)CC1>>Fc1ccc(-c2n[nH]c(CC3CCNCC3)c2-c2ccncc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c29682e0b23047cf9c54eab8703177eb | CC(=O)Cl.CC(C)(C)OC(=O)N1CCN(c2[nH]nc(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1.CO>>C#CCn1nc(N2CCNCC2)c(-c2ccncc2)c1-c1ccc(Cl)cc1.Cl.Cl.O | Cl.C(C)(=O)Cl.CO.CO.ClC1=CC=C(C=C1)C1=NNC(=C1C1=CC=NC=C1)N1CCN(CC1)C(=O)OC(C)(C)C>>O.Cl.Cl.Cl.ClC1=CC=C(C=C1)C1=C(C(=NN1CC#C)N1CCNCC1)C1=CC=NC=C1 | O=[C:2]([CH3:3])[Cl:29].CC(C)(C)OC(=O)[N:10]1[CH2:9][CH2:8][N:7]([c:6]2[nH:5][n:4][c:20](-[c:21]3[cH:22][cH:23][c:24]([Cl:25])[cH:26][cH:27]3)[c:13]2-[c:14]2[cH:15][cH:16][n:17][cH:18][cH:19]2)[CH2:12][CH2:11]1.[CH3:1][OH:31]>>[CH:1]#[C:2][CH2:3][n:4]1[n:5][c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[c:13](-[c:1... | CC(=O)Cl.CC(C)(C)OC(=O)N1CCN(c2[nH]nc(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1.CO | C#CCn1nc(N2CCNCC2)c(-c2ccncc2)c1-c1ccc(Cl)cc1.Cl.Cl.O | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | f509b0242b4ca73794d7a7155a837586bbc4dd1506dd49122ab9f9c4a8dd4350 | 2b0692bf029cf8e18cf2ae87cb1e8cb3a80b7a382d953614367c22133886aba7 | c1ccc(-c2[nH]nc(N3CCNCC3)c2-c2ccncc2)cc1 | C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4](-[c:5]2:[c:6]:[c:7](-[c:8]):[n;H0;D2;+0:9]:[nH;D2;+0:10]:2)-[C:11]-[C:12]-1.O=[C;H0;D3;+0:13](-[CH3;D1;+0:14])-[Cl;H0;D1;+0:15].[CH3;D1;+0:16]-[OH;D1;+0:17]>>[CH;D1;+0:16]#[C;H0;D2;+0:13]-[CH2;D2;+0:14]-[n;H0;D3;+0:9]1:[n;H0;D2;+0:10]:[c:5](-[#7:4]2-[C:3]-[C:2]-[NH... | 90 | [{"value": 90.0, "product": "O.Cl.Cl.Cl.ClC1=CC=C(C=C1)C1=C(C(=NN1CC#C)N1CCNCC1)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 5 | CELSIUS | 1 | HOUR | A solution of HCl in methanol (5 mL) was generated by addition of acetyl chloride (200 mg) to methanol while cooling (5° C.). 3-(4-Chlorophenyl)-4-(4-pyridyl)-5-(4-N-tert.-butoxycarbonylpiperazinyl)pyrazole (100 mg, 0.2 mmol) prepared above was added and the reaction stirred in the cold for one hour. The reaction mixtu... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Carbamic ester.Ether.Methanol.Boc | Secondary amine.Alkyne | C1C[NH]CC[NH]1.c1cn[nH]c1 | c1cn[nH]c1.C1C[NH]CCN1 | c1cn[nH]c1.C1C[NH]CCN1.c1ccncc1.c1ccccc1 | HO- | null | 5 | 1 | CC(=O)Cl.CC(C)(C)OC(=O)N1CCN(c2[nH]nc(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1.CO>>C#CCn1nc(N2CCNCC2)c(-c2ccncc2)c1-c1ccc(Cl)cc1.Cl.Cl.O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8f732a621ba7431f8cd0b56120fcc158 | COC(=O)Cl.COC(=O)Cl.Clc1ccc(-c2n[nH]c(N3CCNCC3)c2-c2ccncc2)cc1>>COC(=O)N1CCN(c2n[nH]c(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1.O | ClC(=O)OC.ClC1=CC=C(C=C1)C1=NNC(=C1C1=CC=NC=C1)N1CCNCC1.ClC(=O)OC>>O.ClC1=CC=C(C=C1)C1=C(C(=NN1)N1CCN(CC1)C(=O)OC)C1=CC=NC=C1 | Cl[C:3]([O:2][CH3:1])=[O:4].COC(Cl)=[O:29].[NH:5]1[CH2:6][CH2:7][N:8]([c:9]2[nH:10][n:11][c:12](-[c:13]3[cH:14][cH:15][c:16]([Cl:17])[cH:18][cH:19]3)[c:20]2-[c:21]2[cH:22][cH:23][n:24][cH:25][cH:26]2)[CH2:27][CH2:28]1>>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([c:9]2[n:10][nH:11][c:12](-[c:13]3[cH:14][cH:15][c... | COC(=O)Cl.COC(=O)Cl.Clc1ccc(-c2n[nH]c(N3CCNCC3)c2-c2ccncc2)cc1 | COC(=O)N1CCN(c2n[nH]c(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1.O | null | CN(C1=CC=NC=C1)C | N1=CC=CC=C1 | Protection | OtherReaction | 0e02fc91170b49b5aa2dca8c80b08a118529932c2c18cd69f9b50afc29bf35d6 | fed6af1de63673a8c49fb23c3aff5dc52a5e8e165cca4fe8707334eafa4bd550 | c1ccc(-c2[nH]nc(N3CCNCC3)c2-c2ccncc2)cc1 | C-O-C(-Cl)=[O;H0;D1;+0:1].Cl-[C;H0;D3;+0:2](=[O;D1;H0:3])-[#8:4]-[C;D1;H3:5].[c:6]-[c:7]1:[c:8]:[c:9](-[#7:10]2-[C:11]-[C:12]-[NH;D2;+0:13]-[C:14]-[C:15]-2):[nH;D2;+0:16]:[n;H0;D2;+0:17]:1>>[C;D1;H3:5]-[#8:4]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[N;H0;D3;+0:13]1-[C:12]-[C:11]-[#7:10](-[c:9]2:[c:8]:[c:7](-[c:6]):[nH;D2;+0:17]:[... | 48 | [{"value": 48.0, "product": "O.ClC1=CC=C(C=C1)C1=C(C(=NN1)N1CCN(CC1)C(=O)OC)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 3 | HOUR | Methyl chloroformate (55 mg) was added to a solution of 3-(4-chlorophenyl)-4-(4-pyridyl)-5-(4-piperazinyl)pyrazole (200 mg, 0.54 mmol; prepared as set forth in Example A-169) and 4-dimethylaminopyridine (5 mg) in pyridine (10 mL). The mixture was stirred at room temperature for 3 hours. Additional methyl chloroformate ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Acyl halide.Ether.Ether.Secondary amine | Carbamic ester.Ether | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1cn[nH]c1.c1ccccc1.c1ccncc1 | HCl | CN(C1=CC=NC=C1)C.N1=CC=CC=C1 | null | 3 | COC(=O)Cl.COC(=O)Cl.Clc1ccc(-c2n[nH]c(N3CCNCC3)c2-c2ccncc2)cc1>CN(C1=CC=NC=C1)C.N1=CC=CC=C1>COC(=O)N1CCN(c2n[nH]c(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1.O |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-79afce2fa3924dc5b9705bb990752660 | Clc1ccc(-c2n[nH]c(N3CCNCC3)c2-c2ccncc2)cc1.O=C1CCC(=O)O1>>O.O.O=C(O)CCC(=O)N1CCN(c2n[nH]c(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1 | ClC1=CC=C(C=C1)C1=NNC(=C1C1=CC=NC=C1)N1CCNCC1.C1(CCC(=O)O1)=O>>O.O.ClC1=CC=C(C=C1)C1=C(C(=NN1)N1CCN(CC1)C(CCC(=O)O)=O)C1=CC=NC=C1 | [NH:10]1[CH2:11][CH2:12][N:13]([c:14]2[nH:15][n:16][c:17](-[c:18]3[cH:19][cH:20][c:21]([Cl:22])[cH:23][cH:24]3)[c:25]2-[c:26]2[cH:27][cH:28][n:29][cH:30][cH:31]2)[CH2:32][CH2:33]1.[O:1]=[C:8]1[O:5][C:4](=[O:3])[CH2:6][CH2:7]1>>[OH2:1].[OH2:2].[O:3]=[C:4]([OH:5])[CH2:6][CH2:7][C:8](=[O:9])[N:10]1[CH2:11][CH2:12][N:13]([... | Clc1ccc(-c2n[nH]c(N3CCNCC3)c2-c2ccncc2)cc1.O=C1CCC(=O)O1 | O.O.O=C(O)CCC(=O)N1CCN(c2n[nH]c(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1 | null | CN(C1=CC=NC=C1)C | null | Functional Group Addition | OtherReaction | 02167a30770a77e8035d02274783b892ce713006cddb323eb2cb80946d0186fb | 2b0361106072ffa92111156a29af982a2a07689a390bf1c6a6a152f5698f2dc0 | c1ccc(-c2[nH]nc(N3CCNCC3)c2-c2ccncc2)cc1 | [O;D1;H0:1]=[C:2]1-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;H0;D1;+0:6])-[O;H0;D2;+0:7]-1.[c:8]-[c:9]1:[c:10]:[c:11](-[#7:12]2-[C:13]-[C:14]-[NH;D2;+0:15]-[C:16]-[C:17]-2):[nH;D2;+0:18]:[n;H0;D2;+0:19]:1>>[O;D1;H0:1]=[C:2](-[OH;D1;+0:7])-[C:3]-[C:4]-[C;H0;D3;+0:5](=[O;D1;H0:20])-[N;H0;D3;+0:15]1-[C:14]-[C:13]-[#7:12](-[c:11]2:[c... | 58 | [{"value": 58.0, "product": "O.O.ClC1=CC=C(C=C1)C1=C(C(=NN1)N1CCN(CC1)C(CCC(=O)O)=O)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | A solution of 3-(4-chlorophenyl)-4-(4-pyridyl)-5-(4-piperzinyl)pyrazole (200 mg; 0.54 mmol; prepared as set forth in Example A-169), succinic anhydride (60 mg, 0.55 mmol) and 4-dimethylaminopyridine (5 mg) was stirred at room temperature for 24 hours. The solvent was removed in vacuo and the residue treated with methan... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Secondary amine | Carboxylic acid.Tertiary amide | C1CNCC[NH]1.C1CCOC1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1cn[nH]c1.c1ccccc1.c1ccncc1 | Other | CN(C1=CC=NC=C1)C | null | 24 | Clc1ccc(-c2n[nH]c(N3CCNCC3)c2-c2ccncc2)cc1.O=C1CCC(=O)O1>CN(C1=CC=NC=C1)C>O.O.O=C(O)CCC(=O)N1CCN(c2n[nH]c(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-b9af1afd69274b8d86e5c594287bb052 | CCOC1(O[Si](C)(C)C)CC1.Clc1ccc(-c2n[nH]c(N3CCNCC3)c2-c2ccncc2)cc1>>Clc1ccc(-c2[nH]nc(N3CCN(C4CC4)CC3)c2-c2ccncc2)cc1 | C(C)OC1(CC1)O[Si](C)(C)C.ClC1=CC=C(C=C1)C1=NNC(=C1C1=CC=NC=C1)N1CCNCC1.C(#N)[BH3-].[Na+].C(C)(=O)O>>ClC1=CC=C(C=C1)C1=C(C(=NN1)N1CCN(CC1)C1CC1)C1=CC=NC=C1 | CCO[C:14]1(O[Si](C)(C)C)[CH2:15][CH2:16]1.[Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][nH:8][c:9]([N:10]3[CH2:11][CH2:12][NH:13][CH2:17][CH2:18]3)[c:19]2-[c:20]2[cH:21][cH:22][n:23][cH:24][cH:25]2)[cH:26][cH:27]1>>[Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[nH:7][n:8][c:9]([N:10]3[CH2:11][CH2:12][N:13]([CH:14]4[CH2:15][CH2:16]... | CCOC1(O[Si](C)(C)C)CC1.Clc1ccc(-c2n[nH]c(N3CCNCC3)c2-c2ccncc2)cc1 | Clc1ccc(-c2[nH]nc(N3CCN(C4CC4)CC3)c2-c2ccncc2)cc1 | null | null | CO | Heteroatom Alkylation and Arylation | OtherReaction | 607f9b7d2366723fd12e941369c42f5b4c0d36ce239278f2bebe31ef811fa60c | d68204a4cfa34cff6cd0e9ec3beba0b05875e761733cc428bd8f8c7f1d92fb07 | c1ccc(-c2[nH]nc(N3CCN(C4CC4)CC3)c2-c2ccncc2)cc1 | C-C-O-[C;H0;D4;+0:1]1(-O-[Si](-C)(-C)-C)-[C:2]-[C:3]-1.[c:4]-[c:5]1:[c:6]:[c:7](-[#7:8]2-[C:9]-[C:10]-[NH;D2;+0:11]-[C:12]-[C:13]-2):[nH;D2;+0:14]:[n;H0;D2;+0:15]:1>>[c:4]-[c:5]1:[c:6]:[c:7](-[#7:8]2-[C:9]-[C:10]-[N;H0;D3;+0:11](-[CH;D3;+0:1]3-[C:2]-[C:3]-3)-[C:12]-[C:13]-2):[n;H0;D2;+0:14]:[nH;D2;+0:15]:1 | 63 | [{"value": 63.0, "product": "ClC1=CC=C(C=C1)C1=C(C(=NN1)N1CCN(CC1)C1CC1)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | null | null | 5 | MINUTE | To a solution of 3-(4-chlorophenyl)-4-(4-pyridyl)-5-(4-piperazinyl)pyrazole (1.95-g; 5.8 mmoles; prepared as set forth in Example A-169) and acetic acid (3.6 g, 60 mmol) containing SA molecular sieves (6 g) was added [(1-ethoxycyclopropyl)oxy]trimethylsilane (6 g, 35 mmol). After stirring for 5 minutes, sodium cyanobor... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Secondary amine.Silyl protective group | Tertiary amine | C1CC1.C1C[NH]CCN1 | C1C[NH]CC[NH]1.C1CC1 | c1ccccc1.c1cn[nH]c1.C1C[NH]CC[NH]1.C1CC1.c1ccncc1 | HO- | CO | null | 0.083333 | CCOC1(O[Si](C)(C)C)CC1.Clc1ccc(-c2n[nH]c(N3CCNCC3)c2-c2ccncc2)cc1>CO>Clc1ccc(-c2[nH]nc(N3CCN(C4CC4)CC3)c2-c2ccncc2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-8a51e9fbfd424ea284f812afdea561e0 | Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1.Nc1ccccc1F>>Fc1ccc(-c2n[nH]cc2-c2ccnc(Nc3ccccc3F)n2)cc1 | ClC1=NC=CC(=N1)C=1C(=NNC1)C1=CC=C(C=C1)F.FC1=C(N)C=CC=C1>>FC1=C(C=CC=C1)NC1=NC=CC(=N1)C=1C(=NNC1)C1=CC=C(C=C1)F | Cl[c:15]1[n:14][cH:13][cH:12][c:11](-[c:10]2[c:6](-[c:5]3[cH:4][cH:3][c:2]([F:1])[cH:26][cH:25]3)[n:7][nH:8][cH:9]2)[n:24]1.[NH2:16][c:17]1[cH:18][cH:19][cH:20][cH:21][c:22]1[F:23]>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][nH:8][cH:9][c:10]2-[c:11]2[cH:12][cH:13][n:14][c:15]([NH:16][c:17]3[cH:18][cH:19][cH:20][cH:21][... | Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1.Nc1ccccc1F | Fc1ccc(-c2n[nH]cc2-c2ccnc(Nc3ccccc3F)n2)cc1 | null | CO | null | Heteroatom Alkylation and Arylation | Goldberg coupling aryl amine-aryl chloride | c38b7155556ff28144ae37859ff6668b20d59da60c705d26b158542b6d8385da | 71a04ae650defc5edd86a92f43c304e981a05f07ff76248da8d4155f3905a29d | c1ccc(Nc2nccc(-c3c[nH]nc3-c3ccccc3)n2)cc1 | Cl-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[#7;a:4]:[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9]>>[c:5]:[#7;a:4]:[c;H0;D3;+0:1](-[NH;D2;+0:6]-[c:7](:[c:8]):[c:9]):[#7;a:2]:[c:3] | 77 | [{"value": 77.0, "product": "FC1=C(C=CC=C1)NC1=NC=CC(=N1)C=1C(=NNC1)C1=CC=C(C=C1)F", "details": "PERCENTYIELD", "is_desired": false}] | 180 | CELSIUS | null | null | A mixture of 2-chloro-4-[3-(4-fluorophenyl)-1H-pyrazol-4-yl]pyrimidine (0.37 g; 0.0013 mol; prepared as set forth in Example A-299), 7 mL of 2-fluoroaniline and 2 drops of methanol was heated at 180° C. in a sealed tube for 16 hours. Excess amine was removed by vacuum distillation and the residue was treated with ethyl... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Primary amine | Secondary amine | c1cncnc1 | c1cncnc1 | c1ccccc1.c1cn[nH]c1.c1cncnc1.c1ccccc1 | HCl | CO | 180 | null | Fc1ccc(-c2n[nH]cc2-c2ccnc(Cl)n2)cc1.Nc1ccccc1F>CO>Fc1ccc(-c2n[nH]cc2-c2ccnc(Nc3ccccc3F)n2)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-6ee0bdc742a745a892e2c81122a50cd0 | C=O.Clc1ccc(-c2[nH]nc(N3CCNCC3)c2-c2ccncc2)cc1>>CN1CCN(c2n[nH]c(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1 | ClC1=CC=C(C=C1)C1=C(C(=NN1)N1CCNCC1)C1=CC=NC=C1.C=O>>ClC1=CC=C(C=C1)C1=C(C(=NN1)N1CCN(CC1)C)C1=CC=NC=C1 | O=[CH2:1].[NH:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][nH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]3)[c:17]2-[c:18]2[cH:19][cH:20][n:21][cH:22][cH:23]2)[CH2:24][CH2:25]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][nH:8][c:9](-[c:10]3[cH:11][cH:12][c:13]([Cl:14])[cH:15][cH:16]3)[c:17]2-[c:18]2[cH:19][cH:20... | C=O.Clc1ccc(-c2[nH]nc(N3CCNCC3)c2-c2ccncc2)cc1 | CN1CCN(c2n[nH]c(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1 | null | null | C(=O)O | Heteroatom Alkylation and Arylation | Eschweiler-Clarke Secondary Amine Methylation | bebbbc2e5c9880d648b53dd51b2cf84a8e9c9861f8ae46f927ebe311ad1ddfb0 | e1fdef8fde1c506d7c9deb8fd5e6f322eceea2abce3167abcf412a1fa4fd5443 | c1ccc(-c2[nH]nc(N3CCNCC3)c2-c2ccncc2)cc1 | O=[CH2;D1;+0:1].[#7:2]1-[C:3]-[C:4]-[NH;D2;+0:5]-[C:6]-[C:7]-1>>[CH3;D1;+0:1]-[N;H0;D3;+0:5]1-[C:4]-[C:3]-[#7:2]-[C:7]-[C:6]-1 | 68 | [{"value": 68.0, "product": "ClC1=CC=C(C=C1)C1=C(C(=NN1)N1CCN(CC1)C)C1=CC=NC=C1", "details": "PERCENTYIELD", "is_desired": false}] | 60 | CELSIUS | 16 | HOUR | The compound of Example A-170 was also synthesized in the following manner. 1-[5-(4-Chlorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]piperazine (12.2 g, 36 mmol, prepared as set forth in Example A-169), 88% formic acid (20 ml), and formaldehyde (37% formalin solution; 44 g, 540 mmol) were combined and stirred at 60° C. fo... | 10.6084/m9.figshare.5104873.v1 | null | Formaldehyde.Secondary amine | Tertiary amine | C1CNCC[NH]1 | C1C[NH]CC[NH]1 | C1C[NH]CC[NH]1.c1cn[nH]c1.c1ccccc1.c1ccncc1 | Other | C(=O)O | 60 | 16 | C=O.Clc1ccc(-c2[nH]nc(N3CCNCC3)c2-c2ccncc2)cc1>C(=O)O>CN1CCN(c2n[nH]c(-c3ccc(Cl)cc3)c2-c2ccncc2)CC1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-5e5de61c27764bc6a4d1626afe7d0a8c | O=C(Cc1ccncc1)c1ccc(Cl)cc1.S=C=S>>O=C(C(=C1SCS1)c1ccncc1)c1ccc(Cl)cc1 | N1=CC=C(C=C1)CC(=O)C1=CC=C(C=C1)Cl.C([O-])([O-])=O.[K+].[K+].BrCBr.C(=S)=S.C([O-])([O-])=O.[K+].[K+].C(=S)=S>>ClC1=CC=C(C=C1)C(C(C1=CC=NC=C1)=C1SCS1)=O | [O:1]=[C:2]([CH2:3][c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1.[C:4](=[S:5])=[S:7]>>[O:1]=[C:2]([C:3](=[C:4]1[S:5][CH2:6][S:7]1)[c:8]1[cH:9][cH:10][n:11][cH:12][cH:13]1)[c:14]1[cH:15][cH:16][c:17]([Cl:18])[cH:19][cH:20]1 | O=C(Cc1ccncc1)c1ccc(Cl)cc1.S=C=S | O=C(C(=C1SCS1)c1ccncc1)c1ccc(Cl)cc1 | null | null | CC(=O)C | Heteroatom Alkylation and Arylation | OtherReaction | 45739c82b492cab85da91dc7e10d4ad2aca0010f979d0ecc36adfc3be01ea86d | f2df0f382e7f6df1891c311da091c26cb669c7e7671ba8f75a8e799bf7582e3d | O=C(C(=C1SCS1)c1ccncc1)c1ccccc1 | [O;D1;H0:1]=[C:2](-[c:3])-[CH2;D2;+0:4]-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1.[S;H0;D1;+0:11]=[C;H0;D2;+0:12]=[S;H0;D1;+0:13]>>[O;D1;H0:1]=[C:2](-[c:3])-[C;H0;D3;+0:4](=[C;H0;D3;+0:12]1-[S;H0;D2;+0:11]-[C:14]-[S;H0;D2;+0:13]-1)-[c:5]1:[c:6]:[c:7]:[#7;a:8]:[c:9]:[c:10]:1 | 81.7 | [{"value": 81.7, "product": "ClC1=CC=C(C=C1)C(C(C1=CC=NC=C1)=C1SCS1)=O", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 24 | HOUR | To a solution of 2-(4-pyridyl)-1-(4-chlorophenyl)ethanone (70.0 g, 0.3 mol) prepared in a similar manner as the compound of Step 1 of Example A-19, dibromomethane (200 mL) and carbon disulfide (25.9 g, 0.34 mol) in acetone (800 mL) was added potassium carbonate (83.0 g, 0.6 mol). The reaction mixture was stirred at roo... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Ketone.Monosulfide.Monosulfide | null | C1SCS1 | C1SCS1.c1ccncc1.c1ccccc1 | Other | CC(=O)C | null | 24 | O=C(Cc1ccncc1)c1ccc(Cl)cc1.S=C=S>CC(=O)C>O=C(C(=C1SCS1)c1ccncc1)c1ccc(Cl)cc1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-94b9789562d44bf8a7bef0413f87460b | CC1CNCC(C)N1.NN.O=C(C(=C1SCS1)c1ccncc1)c1ccc(Cl)cc1>>CC1CN(c2n[nH]c(-c3ccc(Cl)cc3)c2-c2ccncc2)CC(C)N1 | NN.ClC1=CC=C(C=C1)C(C(C1=CC=NC=C1)=C1SCS1)=O.CC1NC(CNC1)C>>ClC1=CC=C(C=C1)C1=C(C(=NN1)N1CC(NC(C1)C)C)C1=CC=NC=C1 | [CH3:1][CH:2]1[CH2:3][NH:4][CH2:23][CH:24]([CH3:25])[NH:26]1.[NH2:6][NH2:7].O=[C:8]([c:9]1[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]1)[C:16](=[C:5]1SCS1)[c:17]1[cH:18][cH:19][n:20][cH:21][cH:22]1>>[CH3:1][CH:2]1[CH2:3][N:4]([c:5]2[n:6][nH:7][c:8](-[c:9]3[cH:10][cH:11][c:12]([Cl:13])[cH:14][cH:15]3)[c:16]2-[c:17]2[cH:1... | CC1CNCC(C)N1.NN.O=C(C(=C1SCS1)c1ccncc1)c1ccc(Cl)cc1 | CC1CN(c2n[nH]c(-c3ccc(Cl)cc3)c2-c2ccncc2)CC(C)N1 | null | null | O1CCCC1.C1(=CC=CC=C1)C | Aromatic Heterocycle Formation | OtherReaction | 4ba032ef00e1aab4abb44832e59f1d5d02c4d73b36f1a2c5cf3b1813dc5309f7 | 1e5f9b38d7db4fe595144f898e5235f6b6271ba8ecf3ac3e92120040e09a299c | c1ccc(-c2[nH]nc(N3CCNCC3)c2-c2ccncc2)cc1 | O=[C;H0;D3;+0:1](-[C;H0;D3;+0:2](=[C;H0;D3;+0:3]1-S-C-S-1)-[c;H0;D3;+0:4]1:[c:5]:[c:6]:[#7;a:7]:[c:8]:[c:9]:1)-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14].[#7:15]1-[C:16]-[C:17]-[NH;D2;+0:18]-[C:19]-[C:20]-1.[NH2;D1;+0:21]-[NH2;D1;+0:22]>>[c:12]:[c:11]:[c;H0;D3;+0:10](-[c;H0;D3;+0:1]1:[nH;D2;+0:22]:[n;H0;D2;+0:21]:[c... | null | [] | null | null | 1 | HOUR | A mixture of 1-(4-chlorophenyl)-2-(1,3-dithietan-2-ylidene)-2-(4-pyridinyl)ethanone (3.2 g, 0.01 mol; prepared as set forth in step 1 of Example A-341) and 2,6-dimethylpiperazine (3.43 g, 0.03 mol) in 35 mL of toluene was heated at reflux for 12 hours. Toluene and excess 2,6-dimethylpiperazine were then removed under v... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Secondary amine.Monosulfide.Monosulfide | Tertiary amine | C1CNCCN1.C1SCS1 | C1CNCC[NH]1.c1cn[nH]c1 | C1CNCC[NH]1.c1cn[nH]c1.c1ccccc1.c1ccncc1 | Other | O1CCCC1.C1(=CC=CC=C1)C | null | 1 | CC1CNCC(C)N1.NN.O=C(C(=C1SCS1)c1ccncc1)c1ccc(Cl)cc1>O1CCCC1.C1(=CC=CC=C1)C>CC1CN(c2n[nH]c(-c3ccc(Cl)cc3)c2-c2ccncc2)CC(C)N1 |
ord_dataset-c3a75813d0b24864aa4f7cd526efd6aa | ord-c3c882500a8d45a88c6af2dd611204ff | CN.CN1CCC(=O)CC1>>CNC1CCN(C)CC1 | CN1CCC(CC1)=O.O1CCCC1.CN>>CN1CCC(CC1)NC | [CH3:1][NH2:2].O=[C:3]1[CH2:4][CH2:5][N:6]([CH3:7])[CH2:8][CH2:9]1>>[CH3:1][NH:2][CH:3]1[CH2:4][CH2:5][N:6]([CH3:7])[CH2:8][CH2:9]1 | CN.CN1CCC(=O)CC1 | CNC1CCN(C)CC1 | null | [Pd] | CO | Heteroatom Alkylation and Arylation | Reductive amination with ketone | 42e9e55fb09951ae64da272b20a0fe6708e6155493933c6a5b57bd203fbe3626 | 07faf85ffe990e88a1de7fd04a339bf226f78d8bfae9712ea59eebd76bb54b9f | C1CCNCC1 | O=[C;H0;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1.[C;D1;H3:7]-[NH2;D1;+0:8]>>[C;D1;H3:7]-[NH;D2;+0:8]-[CH;D3;+0:1]1-[C:2]-[C:3]-[#7:4]-[C:5]-[C:6]-1 | 87 | [{"value": 87.0, "product": "CN1CCC(CC1)NC", "details": "PERCENTYIELD", "is_desired": false}, {"value": 86.7, "product": "CN1CCC(CC1)NC", "details": "CALCULATEDPERCENTYIELD", "is_desired": false}] | null | null | 2 | HOUR | A mixture of 1-methyl-4-piperidone (20 g, 0.18 mol) in methanol:tetrahydrofuran (100 mL, 1:1) and methyl amine (2 M in tetrahydrofuran, 3 mole excess) was placed in a Parr shaker with 5% Pd/C and hydrogenated for two hours at 60 psi and 70° C. The catalyst was filtered and the filtrate concentrated on the rotary evapor... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Primary amine | Secondary amine | C1CC[NH]CC1 | C1CC[NH]CC1 | C1CC[NH]CC1 | Other | [Pd].CO | null | 2 | CN.CN1CCC(=O)CC1>[Pd].CO>CNC1CCN(C)CC1 |
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