source stringlengths 10 15 | canonical_rxn stringlengths 21 868 | catalyst1 stringclasses 53
values | solvent1 stringclasses 84
values | solvent2 stringclasses 40
values | reagent1 stringclasses 222
values | reagent2 stringclasses 94
values | dataset stringclasses 1
value |
|---|---|---|---|---|---|---|---|
US20100016574A1 | CNC(=O)CCO[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1n1ccc(=O)[nH]c1=O.COc1ccc(C(Cl)(c2ccccc2)c2ccc(OC)cc2)cc1>>CNC(=O)CCO[C@@H]1[C@H](O)[C@@H](COC(c2ccccc2)(c2ccc(OC)cc2)c2ccc(OC)cc2)O[C@H]1n1ccc(=O)[nH]c1=O | null | c1ccncc1 | null | null | null | train |
US05219856 | BrCc1ccc(Br)cc1.CCCc1nc(C(=O)OC)c(C(=O)OC)[nH]1>>CCCc1nc(C(=O)OC)c(C(=O)OC)n1Cc1ccc(Br)cc1 | null | CN(C)C=O | null | O | O=C([O-])[O-].[K+].[K+] | train |
US20130274253A1 | CCN=C=NCCCN(C)C.CN(C)C=O.Cn1c(CC(=O)[O-])nc(N2CCOCC2)cc1=O.O=C(Cc1nc(N2CCOCC2)cc(=O)[nH]1)N1CCc2c(OC(F)F)cccc21.c1ccncc1>>CN1CCN(Cc2cccc3c2CCN3C(=O)Cc2nc(N3CCOCC3)cc(=O)n2C)CC1 | null | CN(C)C=O | null | Cl | null | train |
US20060247273A1 | CC(C)(C)OC(=O)CCNC(=O)Nc1c(C(=O)Nc2ccc(Cl)cn2)oc2ccccc12>>O=C(O)CCNC(=O)Nc1c(C(=O)Nc2ccc(Cl)cn2)oc2ccccc12 | null | O=C(O)C(F)(F)F | null | null | null | train |
US20150299165A1 | CC(C)(C)N.Cc1nnc(CCl)o1>>Cc1nnc(CNC(C)(C)C)o1 | null | CN(C)C=O | null | null | null | train |
US20120035206A1 | O=C1/C(=C/Cl)CSc2ccc(F)cc21>>O=C1/C(=C\Cl)CSc2ccc(F)cc21 | null | CO | null | null | null | train |
US20130157996A1 | CC(C)(C)OC(=O)CN.O=C(OCc1ccccc1)c1ccc(=O)oc1>>CC(C)(C)OC(=O)Cn1cc(C(=O)OCc2ccccc2)ccc1=O | null | CO | null | Cl | null | train |
US04752326 | CC(=O)C(C)C(C)=O.CS(=O)(=O)Oc1cc(NN)c(F)cc1Cl>>Cc1nn(-c2cc(OS(C)(=O)=O)c(Cl)cc2F)c(C)c1C | null | Cc1ccccc1 | null | CCO | O | train |
US20150329538A1 | Cc1nc2ccc(F)c(-c3cc(C(=O)O)c(C)[nH]3)c2nc1NC1(C)CC1.N>>Cc1nc2ccc(F)c(-c3cc(C(N)=O)c(C)[nH]3)c2nc1NC1(C)CC1 | null | CN(C)C=O | ClCCl | CCN(C(C)C)C(C)C | null | train |
US20080108828A1 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.COC(=O)[C@@H]1COC(C(C)C)N1>>COC(=O)[C@@H]1CO[C@H](C(C)C)N1C(=O)OC(C)(C)C | null | C1CCOC1 | null | null | null | train |
US05264577 | CCOC(=O)C[N+](=O)[O-].OC1c2ccccc2Oc2ccccc21>>CCOC(=O)C(C1c2ccccc2Oc2ccccc21)[N+](=O)[O-] | null | O | null | CCO | [K+].[OH-] | train |
US20050153942A1 | CCOC(=O)C(=O)C(Cl)C(C)=O.Nc1cc[nH]n1>>CCOC(=O)c1nc2ccnn2c(C)c1Cl | null | CC#N | CCO | C1CCNCC1 | null | train |
US09388147B2 | COC(=O)CCN[C@@H]1CCc2c(-c3noc(-c4ccc(OC(C)C)c(C#N)c4)n3)cccc21>>CC(C)Oc1ccc(-c2nc(-c3cccc4c3CC[C@H]4NCCC(=O)O)no2)cc1C#N | null | CCO | null | Cl | [Na+].[OH-] | train |
US05498774 | N#CC(N)c1cccc(Cl)c1.O=C(O)c1cccn2cc(-c3ccccc3)nc12>>N#CC(NC(=O)c1cccn2cc(-c3ccccc3)nc12)c1cccc(Cl)c1 | null | CC#N | null | O=P(Cl)(Cl)Cl | O=C([O-])O.[Na+] | train |
US20130040931A1 | Cc1cccc(C(=O)N2CCCC2)c1-c1ccc(N)c(C=O)c1.N#CCC1=CCCC1>>Cc1cccc(C(=O)N2CCCC2)c1-c1ccc2nc(N)c(C3=CCCC3)cc2c1 | null | CS(C)=O | null | [K+].[OH-] | null | train |
US20150057450A1 | COCCCl.c1ccc2[nH]cnc2c1>>COCCn1cnc2ccccc21 | null | CC#N | null | [K+].[OH-] | null | train |
US20070197617A1 | CC(=O)OC(C)=O.CC(C)(C)OC(=O)N[C@@H](C(=O)O)c1ccc(N)cc1>>CC(=O)Nc1ccc([C@@H](NC(=O)OC(C)(C)C)C(=O)O)cc1 | null | ClCCl | null | c1ccncc1 | null | train |
US20160229816A1 | N#Cc1[nH]nnc1-c1csc(-c2cccc(C(F)(F)F)c2)n1.O=C1CCC(=O)N1Cl>>N#Cc1[nH]nnc1-c1nc(-c2cccc(C(F)(F)F)c2)sc1Cl | null | CC#N | null | null | null | train |
US20080009482A1 | CN1CCC(N)CC1.COc1ccc(C(=O)O)cc1[N+](=O)[O-]>>COc1ccc(C(=O)NC2CCN(C)CC2)cc1[N+](=O)[O-] | null | CN(C)C=O | null | CCN(C(C)C)C(C)C | CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F | train |
US20140038910A1 | CCOC(=O)C[C@H](NC(=O)CNC(=O)c1cc(O)cc(NC2=NCC(O)CN2)c1)c1cc(Cl)cc(C(C)(C)COC)c1>>COCC(C)(C)c1cc(Cl)cc([C@H](CC(=O)O)NC(=O)CNC(=O)c2cc(O)cc(NC3=NCC(O)CN3)c2)c1 | null | CC#N | O | [Li+].[OH-] | null | train |
US20080275037A1 | C[C@@H](N)c1ccc(C(F)(F)F)nc1.Clc1ncnc2c1CN(Cc1ccccc1)CC2>>C[C@@H](Nc1ncnc2c1CN(Cc1ccccc1)CC2)c1ccc(C(F)(F)F)nc1 | null | CC#N | null | CCN(C(C)C)C(C)C | null | train |
US07176310B1 | COC(=O)[C@H](O)c1ccccc1.CS(=O)c1ncc(C(=O)Nc2ccc(F)cc2)cn1>>COC(=O)[C@H](Oc1ncc(C(=O)Nc2ccc(F)cc2)cn1)c1ccccc1 | null | C1CCOC1 | null | C1CCC2=NCCCN2CC1 | null | train |
US04251541 | CCN1CC2OC2C1.Sc1ccccc1Cl>>CCN1C[C@@H](Sc2ccccc2Cl)[C@H](O)C1 | Cl | ClCCl | null | null | null | train |
US06303593B1 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.OCC1CCNCC1>>CC(C)(C)OC(=O)N1CCC(CO)CC1 | null | ClCCl | null | [Na+].[OH-] | null | train |
US04954507 | Cl.OCC1CN(Cc2ccccc2)CCN1Cc1ccccc1>>ClCC1CN(Cc2ccccc2)CCN1Cc1ccccc1 | null | O=S(Cl)Cl | null | Cl | null | train |
US07026336B1 | COc1cc(-c2nc(C(C)(C)CNC(=O)OC(C)(C)C)[nH]c2-c2ccncc2)ccc1Cl>>COc1cc(-c2nc(C(C)(C)CN)[nH]c2-c2ccncc2)ccc1Cl | null | ClCCl | null | O=C(O)C(F)(F)F | null | train |
US20140114068A1 | CC(C)c1ccc2c(c1)OC1(O)c3cccc([N+](=O)[O-])c3C(=O)C21NC(=O)c1ccc([N+](=O)[O-])cc1>>CC(C)c1ccc2c(c1)OC1(O)c3cccc(N)c3C(=O)C21NC(=O)c1ccc([N+](=O)[O-])cc1 | [Fe] | CCO | O | null | null | train |
US05223536 | Fc1ccc(CCCC(c2ccc(Cl)cc2)C2CC2)cc1Oc1ccccc1.O=C1CCC(=O)N1Br>>Fc1ccc(C(Br)CCC(c2ccc(Cl)cc2)C2CC2)cc1Oc1ccccc1 | null | ClC(Cl)(Cl)Cl | null | null | null | train |
US20060025459A1 | CCn1ccc2c(N(S(=O)(=O)CCCCl)S(=O)(=O)CCCCl)cc(C(=O)OC)cc21>>CCn1ccc2c(NS(=O)(=O)CCCCl)cc(C(=O)O)cc21 | null | CO | null | [Na+].[OH-] | null | train |
US20020032168A1 | CC(=O)OC[C@H]1O[C@@H](n2cnc3c(NCC4c5ccccc5-c5ccccc54)nc(C#N)nc32)[C@H](OC(C)=O)[C@@H]1OC(C)=O>>NCc1nc(NCC2c3ccccc3-c3ccccc32)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1 | [Pd] | CCO | null | N | null | train |
US20070167413A1 | C1CNCCN1.O=[N+]([O-])c1ccc(Br)nc1>>O=[N+]([O-])c1ccc(N2CCNCC2)nc1 | null | C1CCOC1 | null | null | null | train |
US06172085B2 | Cc1c(C)c2c(c(C)c1N)CC(C)(CBr)O2.Fc1ccc(C(NC2CCNCC2)c2ccc(F)cc2)cc1>>Cc1c(C)c2c(c(C)c1N)CC(C)(CN1CCC(NC(c3ccc(F)cc3)c3ccc(F)cc3)CC1)O2 | null | CC(=O)N(C)C | O | O=C([O-])[O-].[K+].[K+] | null | train |
US20150148333A1 | Cc1noc2c1-c1ccc(Cl)cc1NCC2.O=S(=O)(Cl)c1ccccc1>>Cc1noc2c1-c1ccc(Cl)cc1N(S(=O)(=O)c1ccccc1)CC2 | null | c1ccncc1 | null | null | null | train |
US20060116410A1 | COC(=O)c1cc(N)cc(Cl)c1.O=C(Cl)CCCCl>>COC(=O)c1cc(Cl)cc(NC(=O)CCCCl)c1 | null | ClCCl | null | c1ccncc1 | null | train |
US20030069257A1 | CCCNc1ccc(C#N)cc1N.CCOC(=N)CCl.Cl>>CCCn1c(CCl)nc2cc(C#N)ccc21.Cl | null | CCO | null | null | null | train |
US20070244095A1 | Cc1cc2c(cc1C(F)(F)F)NCCC[C@@H]2N(Cc1cc(Cl)cc(C(F)(F)F)c1)c1nnn(C)n1.O=C1CCC(=O)N1Br>>Cc1cc2c(c(Br)c1C(F)(F)F)NCCC[C@@H]2N(Cc1cc(Cl)cc(C(F)(F)F)c1)c1nnn(C)n1 | null | CC(=O)O | null | null | null | train |
US20030008849A1 | CC#CCOc1ccc(S(=O)(=O)N2CC2C(=O)OC)cc1.OCCBr>>CC#CCOc1ccc(S(=O)(=O)NC(COCCBr)C(=O)OC)cc1 | null | CCOC(C)=O | null | CCOCC | FB(F)F | train |
US20040092582A1 | COC(=O)Cl.COc1cc2c(c3c1OC(C)(C)C3)C(c1cccc(-c3ccc(N)cc3)c1)=NC(C)(C)C2>>COC(=O)Nc1ccc(-c2cccc(C3=NC(C)(C)Cc4cc(OC)c5c(c43)CC(C)(C)O5)c2)cc1 | null | C1CCOC1 | O | O=C([O-])[O-].[Na+].[Na+] | null | train |
US20120136148A1 | COC(=O)c1cc(OC(C)=O)c2ccc(OC)cc2c1-c1ccc(Br)cc1.COc1ccc(B(O)O)c(OC)c1>>COC(=O)c1cc(OC(C)=O)c2ccc(OC)cc2c1-c1ccc(-c2ccc(OC)cc2OC)cc1 | null | COCCOC | null | O | O=C([O-])[O-].[Na+].[Na+] | train |
US20090054435A1 | C=CCOC(=O)[C@H](C)O.COc1ccc(C(=O)c2ccc(OCc3nc(-c4ccccc4)oc3C)nc2)c(O)c1>>C=CCOC(=O)[C@@H](C)Oc1cc(OC)ccc1C(=O)c1ccc(OCc2nc(-c3ccccc3)oc2C)nc1 | null | ClCCl | null | CCOC(=O)N=NC(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | train |
US20120094972A1 | CC(C)(C)OC(=O)N1CCSc2ncc(N3CCOCC3)cc21>>c1nc2c(cc1N1CCOCC1)NCCS2 | null | ClCCl | null | O=C(O)C(F)(F)F | null | train |
US20090105325A1 | CC(C)COC(=O)Cl.COC(c1ccc(NC(=O)c2c(C)nn(C)c2C)cc1CC(C)C)(C(F)(F)F)C(F)(F)F>>COC(c1ccc(N(C(=O)OCC(C)C)C(=O)c2c(C)nn(C)c2C)cc1CC(C)C)(C(F)(F)F)C(F)(F)F | null | C1CCOC1 | null | Cl | [H-].[Na+] | train |
US20090221583A1 | COc1ccc(Br)c(C(=O)N2CCN(C(=O)CNC(=O)c3ccc(-c4ccccc4)cc3)CC2)c1>>O=C(NCC(=O)N1CCN(C(=O)c2cc(O)ccc2Br)CC1)c1ccc(-c2ccccc2)cc1 | null | ClCCl | null | BrB(Br)Br | null | train |
US20080021032A1 | CC(C)(C)[Si](C)(C)OCCn1ccc(N)n1.COc1cc([C@@H](CC2CCCC2)C(=O)O)ccc1S(C)(=O)=O>>COc1cc([C@@H](CC2CCCC2)C(=O)Nc2ccn(CCO[Si](C)(C)C(C)(C)C)n2)ccc1S(C)(=O)=O | CN(C)C=O | ClCCl | null | Cc1cccc(C)n1 | O=C(Cl)C(=O)Cl | train |
US08541595B2 | CC(C)(C)OC(=O)CC1(c2ccc(Br)cc2)c2ccccc2-c2nccn21.O=C(O)C(F)(F)F>>O=C(O)CC1(c2ccc(Br)cc2)c2ccccc2-c2[nH+]ccn21.O=C([O-])C(F)(F)F | null | ClCCl | null | null | null | train |
US04766128 | CCN(CC)C(=O)N[C@H]1C=C2c3ccc([N+](=O)[O-])c4c3C(CN4)C[C@H]2N(C)C1>>CCN(CC)C(=O)N[C@H]1C=C2c3ccc([N+](=O)[O-])c4[nH]cc(c34)C[C@H]2N(C)C1 | null | ClCCl | O | O=[Cr](=O)([O-])O[Cr](=O)(=O)[O-].c1cc[nH+]cc1.c1cc[nH+]cc1 | null | train |
US20040006236A1 | Nc1cccc(C(=O)O)c1>>NC1CCCC(C(=O)O)C1 | null | CCO | null | [H][H] | null | train |
US20040204421A1 | CCN1CCN(c2nc(-c3ccc(Br)cc3)cc3ccccc23)CC1.O=C1CCOCC1>>CCN1CCN(c2nc(-c3ccc(C4(O)CCOCC4)cc3)cc3ccccc23)CC1 | null | C1CCOC1 | null | [Li]CCCC | [Cl-].[NH4+] | train |
US04578395 | CC(=O)CC(=O)OCC(C)(C)CN(C)C.COC(=O)/C=C(/C)N.O=Cc1cccc([N+](=O)[O-])c1Cl>>COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)(C)CN(C)C)C1c1cccc([N+](=O)[O-])c1Cl | null | CC(C)O | null | null | null | train |
US20090264445A1 | CC#CC(=O)OCC.OCC1COc2ccccc2O1>>CCOC(=O)/C=C(\C)OCC1COc2ccccc2O1 | null | C1CCOC1 | null | CCCCP(CCCC)CCCC | null | train |
US20100160369A1 | OCCOc1ccc(-c2noc(-c3cn4cc(C(F)(F)F)cc(Cl)c4n3)n2)c(Cl)c1>>O=CCOc1ccc(-c2noc(-c3cn4cc(C(F)(F)F)cc(Cl)c4n3)n2)c(Cl)c1 | null | ClCCl | null | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | null | train |
US20080161315A1 | Fc1cc(F)cc(CBr)c1.O=C(c1c[nH]c2cc(Cl)ccc12)C(F)(F)F>>O=C(c1cn(Cc2cc(F)cc(F)c2)c2cc(Cl)ccc12)C(F)(F)F | null | CC#N | null | O | O=C([O-])[O-].[Cs+].[Cs+] | train |
US20140142258A1 | C#Cc1ccccc1.[N-]=[N+]=NCc1ccccc1>>c1ccc(Cn2cc(-c3ccccc3)nn2)cc1 | null | ClCCl | null | null | null | train |
US05192766 | C#Cc1ccccc1.COC(=O)/C=C\c1cccc(Br)c1>>COC(=O)/C=C(/C#Cc1ccccc1)c1ccccc1 | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | null | null | CCNCC | null | train |
US20160120850A1 | CCOC(=O)c1nc(CC(C)(C)OC)c(-c2ccc(S(=O)(=O)N[C@@H](CC)C(F)(F)F)c(Cl)c2Cl)s1.NN>>CC[C@H](NS(=O)(=O)c1ccc(-c2sc(C(=O)NN)nc2CC(C)(C)OC)c(Cl)c1Cl)C(F)(F)F | null | CCO | null | O | null | train |
US20140249132A1 | CC(=O)c1ccc(Br)cn1.C[Mg]Cl>>CC(C)(O)c1ccc(Br)cn1 | null | C1CCOC1 | C1CCOC1 | null | null | train |
US20100029633A1 | O=P(Br)(Br)Br.O=c1ccc2cccc(Br)c2[nH]1>>Brc1ccc2cccc(Br)c2n1 | null | O | null | null | null | train |
US05594023 | CCN(CC)C(=O)N1CCc2cc(S(=O)(=O)N3C(=O)C(NCCC4CCN(C(=O)OC(C)(C)C)CC4)(c4ccccc4Cl)c4cc(Cl)ccc43)ccc21.O=C(O)C(F)(F)F>>CCN(CC)C(=O)N1CCc2cc(S(=O)(=O)N3C(=O)C(NCCC4CCNCC4)(c4ccccc4Cl)c4cc(Cl)ccc43)ccc21.O.O=C(O)C(F)(F)F | null | ClCCl | null | null | null | train |
US20050065157A1 | CCOC(=O)c1cc2c3ccccc3n(C(C)C)c2cn1>>CC(C)n1c2ccccc2c2cc(C(=O)O)ncc21 | null | CO | O | [Na+].[OH-] | null | train |
US04636519 | CC1(Cl)CSC(=C(C#N)n2ccnc2)S1>>C=C1CSC(=C(C#N)n2ccnc2)S1 | null | C1CCOC1 | null | null | null | train |
US20070105904A1 | CN(C)C=O.Cc1cccc(OCc2ccc(Br)cc2)n1>>Cc1cccc(OCc2ccc(C=O)cc2)n1 | null | C1CCOC1 | CCOC(C)=O | O | [Li]CCCC | train |
US20140018393A1 | Cn1cc(-c2ccc([C@@H]3C[C@H]3N(CC3CCN(C(=O)OC(C)(C)C)CC3)C(=O)C(F)(F)F)cc2)cn1>>Cn1cc(-c2ccc([C@@H]3C[C@H]3N(CC3CCNCC3)C(=O)C(F)(F)F)cc2)cn1 | null | ClCCl | null | O=C(O)C(F)(F)F | null | train |
US20100280001A1 | CCCCc1nc2c(N)nc3ccccc3c2n1CCCN.COC(=O)Cc1ccc(C=O)cc1>>CCCCc1nc2c(N)nc3ccccc3c2n1CCCNCc1ccc(CC(=O)OC)cc1 | CO | C1CCOC1 | CO | [BH4-].[Na+] | null | train |
US20060111362A1 | CC(C)(C)OC(=O)N1CCN(c2ncc(Oc3ccccc3C(N)=O)c3c2n(Cc2ccccc2)c(=O)n3Cc2ccccc2C#N)CC1.O=C(O)C(F)(F)F>>N#Cc1ccccc1Cn1c(=O)n(Cc2ccccc2)c2c(N3CCNCC3)ncc(Oc3ccccc3C(N)=O)c21.O=C(O)C(F)(F)F | null | ClCCl | null | Cc1ccccc1 | null | train |
US20080146565A1 | CN(C)C1CCNCC1.CS(=O)(=O)CCCOc1cccc2c1ccn2-c1ccnc(NC2CCC(C(=O)O)CC2)n1>>CN(C)C1CCN(C(=O)C2CCC(Nc3nccc(-n4ccc5c(OCCCS(C)(=O)=O)cccc54)n3)CC2)CC1 | null | CN(C)C=O | null | O=C(n1ccnc1)n1ccnc1 | null | train |
US04001252 | CCOC(=O)C1=C(C)NC(N)=C(C(=O)OCC)C1c1ccccc1.CI>>CCOC(=O)C1=C(C)N=C(N)C(C)(C(=O)OCC)C1c1ccccc1 | null | CCO | null | C | C[O-].[Na+] | train |
US06083968 | CCSC(F)(F)C1(c2ccc(F)cc2F)CO1.c1nc[nH]n1>>CCSC(F)(F)C(O)(Cn1cncn1)c1ccc(F)cc1F | null | CCOC(C)=O | CS(C)=O | O | O=C([O-])[O-].[K+].[K+] | train |
US20140243302A1 | CN(C)C=O.Cc1ccc([N+](=O)[O-])c(C(=O)CF)n1>>Cc1ccc([N+](=O)[O-])c(C(=O)/C(F)=C/N(C)C)n1 | null | CN(C)C=O | null | CC(=O)N(C)C | null | train |
US20150152077A1 | BrC1CC1.C1CCOC1.COc1ccc2c(=O)c3ccc(OC)cc3oc2c1>>COc1ccc2c(c1)Oc1cc(OC)ccc1C2=C1CCCC1 | null | CCOC(C)=O | null | [Mg] | [Cl-].[NH4+] | train |
US20120202785A1 | O=[N+]([O-])c1ccc(F)cc1Nc1cnccn1>>Nc1ccc(F)cc1Nc1cnccn1 | [Pd] | null | null | null | null | train |
US20160024079A1 | CCc1cc(C)c2c(ccn2C(=O)OC(C)(C)C)c1C(C)(NS(=O)(=O)CC[Si](C)(C)C)c1nc2cc(C#N)cnc2n1COCC[Si](C)(C)C.CI>>CCc1cc(C)c2c(ccn2C(=O)OC(C)(C)C)c1C(C)(c1nc2cc(C#N)cnc2n1COCC[Si](C)(C)C)N(C)S(=O)(=O)CC[Si](C)(C)C | null | CC(C)=O | O | O=C([O-])[O-].[K+].[K+] | null | train |
US20130324576A1 | CC(C)(C)OC(=O)N1CCC(C(C#N)c2ccc(Cl)cc2F)CC1.Cl>>Cl.N#CC(c1ccc(Cl)cc1F)C1CCNCC1 | null | C1COCCO1 | null | null | null | train |
US05409943 | Nc1ncccc1OCc1ccccc1.S=C=Nc1ccc(Cl)cc1>>S=C(Nc1ccc(Cl)cc1)Nc1ncccc1OCc1ccccc1 | null | Cc1ccccc1 | null | CCOCC | null | train |
US20150250769A1 | COC(=O)CCCSc1nnc(-c2ccc(Cl)cc2Cl)o1>>O=C(O)CCCSc1nnc(-c2ccc(Cl)cc2Cl)o1 | null | C1CCOC1 | null | [Na+].[OH-] | null | train |
US20130158273A1 | CC(C)OC(=O)CCCc1nc2cc(N)ccc2n1C.CCOC(C)=O.OCCCl>>CC(C)OC(=O)CCCc1nc2cc(N(CCO)CCO)ccc2n1C | null | CCCCCC | CCOC(C)=O | CCN(CC)CC | O | train |
US20130085161A1 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.N=c1n(Cc2cccc3[nH]nnc23)c2ccccc2n1C1CCN(c2cc(Cl)ccc2[N+](=O)[O-])CC1>>CC(C)(C)OC(=O)N=c1n(Cc2cccc3c2nnn3C(=O)OC(C)(C)C)c2ccccc2n1C1CCN(c2cc(Cl)ccc2[N+](=O)[O-])CC1 | CN(C)c1ccncc1 | ClCCCl | ClCCl | null | null | train |
US20070155744A1 | NCc1cccnc1.O=C(O)c1cc(OCc2ccccc2)c(OCc2ccccc2)c(C(=O)NCc2ccc(F)cc2)n1>>O=C(NCc1cccnc1)c1cc(OCc2ccccc2)c(OCc2ccccc2)c(C(=O)NCc2ccc(F)cc2)n1 | null | ClCCl | null | CCN(CC)CC | O=C1OCCN1P(=O)(Cl)N1CCOC1=O | train |
US20100324003A1 | CC(=O)O[C@@H]1C(=O)CC[C@@]2(C)C1=CC[C@H]1[C@@H]3CCC(=O)[C@@]3(C)CC[C@@H]12>>CC(=O)O[C@H]1C2=CC[C@@H]3[C@H](CC[C@]4(C)[C@@H](O)CC[C@@H]34)[C@@]2(C)CCC1O | null | CO | null | [BH4-].[Na+] | null | train |
US03937837 | CC(=O)Oc1ccc2c(=O)c(C#N)c(C)oc2c1>>Cc1oc2cc(O)ccc2c(=O)c1C#N | null | CO | null | Cl | [Na+].[OH-] | train |
US20070225271A1 | CCOc1cc(CN2CCC(N)CC2)ccc1OC.Fc1ccccc1-c1nc(Cl)nc2ccccc12>>CCOc1cc(CN2CCC(Nc3nc(-c4ccccc4F)c4ccccc4n3)CC2)ccc1OC | null | CN1CCCC1=O | null | null | null | train |
US05439925 | CC(=O)OC(C)c1ccc2c(c1)C(C)(C)CCC2(C)C>>CC(O)c1ccc2c(c1)C(C)(C)CCC2(C)C | null | CO | null | [Na+].[OH-] | null | train |
US20090197862A1 | Cc1ccc(S(=O)(=O)OC2CCC3(CC2)OCCO3)cc1.Ic1cn[nH]c1>>Ic1cnn(C2CCC3(CC2)OCCO3)c1 | null | CN(C)C=O | O | C1COCCOCCOCCOCCOCCO1 | O=C([O-])[O-].[K+].[K+] | train |
US20110034455A1 | CCOC(=O)CC1CC2(CCN(C(=O)OC(C)(C)C)CC2)c2c(Br)cccc21>>CCOC(=O)CC1CC2(CCNCC2)c2c(Br)cccc21 | null | ClCCl | O=C(O)C(F)(F)F | null | null | train |
US20110046397A1 | C=C(C[C@@H](Cc1ccc(-c2ccccc2)cc1)NC(=O)OC(C)(C)C)C(=O)O>>C[C@H](C[C@@H](Cc1ccc(-c2ccccc2)cc1)NC(=O)OC(C)(C)C)C(=O)O | [Pd] | CC(=O)OC(C)C | null | [H][H] | null | train |
US20070066618A1 | Nc1ccc(CCO)cc1.O=[N+]([O-])c1c(Cl)cccc1Cl>>O=[N+]([O-])c1c(Cl)cccc1Nc1ccc(CCO)cc1 | null | O | null | CC(=O)[O-].[Na+] | null | train |
US05167949 | CC(=O)O.CCOCc1nc(N)c2nc(C)cnc2n1>>CCOCc1nc2ncc(C)nc2c(=O)[nH]1 | null | [Na+] | [OH-] | null | null | train |
US20070185168A1 | O=C1CCc2cc(C(=O)CN3CC=C(c4cccs4)CC3)ccc2N1>>O=C1CCc2cc(C(O)CN3CC=C(c4cccs4)CC3)ccc2N1 | null | CCO | null | [BH4-].[Na+] | null | train |
US20040132748A1 | ClCc1cccnc1.Nc1nc(Cl)nc2nc[nH]c12>>Nc1nc(Cl)nc2c1ncn2Cc1cccnc1 | null | CN(C)C=O | null | Cl | O=C([O-])[O-].[K+].[K+] | train |
US20080255083A1 | CN(Cc1ccc(CCn2ccc(OCc3ccccc3)cc2=O)cc1)C(=O)OC(C)(C)C>>CNCc1ccc(CCn2ccc(OCc3ccccc3)cc2=O)cc1 | null | ClCCl | O | O=C(O)C(F)(F)F | O=C([O-])O.[Na+] | train |
US04492707 | CC1Oc2ccccc2C(=O)C1n1ccnc1>>CC1Oc2ccccc2C(O)C1n1ccnc1 | null | CO | null | O | [BH4-].[Na+] | train |
US20110213143A1 | CC(C)CC(=O)OC(C)OC(=O)Oc1ccc([N+](=O)[O-])cc1.NCCC[C@@H](Cc1ncn2c1CCc1ccccc1-2)C(=O)O>>CC(C)CC(=O)OC(C)OC(=O)NCCC[C@@H](Cc1ncn2c1CCc1ccccc1-2)C(=O)O | null | CN(C)C=O | null | O | null | train |
US20080146611A1 | COC(=O)CSc1ccc(Cl)cn1>>O=C(O)CSc1ccc(Cl)cn1 | null | C1CCOC1 | O | Cl | [Li]O | train |
US20060205759A1 | CCOC(=O)C1CCC(Sc2ccc(F)cc2)C(=O)C1>>CCOC(=O)C1CCc2sc3ccc(F)cc3c2C1 | null | CC(Cl)Cl | O | Cl | [Al+3].[Cl-].[Cl-].[Cl-] | train |
US20160137696A1 | CC(C)(C)OC(=O)CCCCCCCCCCCCCCCCC(=O)N[C@@H](CCN=[N+]=[N-])C(=O)O>>[N-]=[N+]=NCC[C@H](NC(=O)CCCCCCCCCCCCCCCCC(=O)O)C(=O)O | null | ClCCl | null | O=C(O)C(F)(F)F | null | train |
US20090312335A1 | COc1c(-c2nnc(Cc3ccc(F)cc3)[nH]2)cn2c1C(=O)N(C)CC2>>CN1CCn2cc(-c3nnc(Cc4ccc(F)cc4)[nH]3)c(O)c2C1=O | null | ClCCl | null | BrB(Br)Br | null | train |
US20070049618A1 | NC1CCC(=O)NC1=O.O=C(O)c1cccc(Nc2ccc3ccccc3c2)c1C(=O)O>>O=C1CCC(N2C(=O)c3cccc(Nc4ccc5ccccc5c4)c3C2=O)C(=O)N1 | null | c1ccncc1 | null | Cl | null | train |
US20130123235A1 | CC(C)(C)O.O=C(O)c1c(CS(=O)(=O)c2ccccc2)ccc(Br)c1O>>CC(C)(C)OC(=O)c1c(CS(=O)(=O)c2ccccc2)ccc(Br)c1O | CN(C)c1ccncc1 | C1CCOC1 | null | C(=NC1CCCCC1)=NC1CCCCC1 | null | train |
US20140112945A1 | COc1ccc(C2=NN(C3CCN(C(=O)[C@H](Cn4cccn4)NC(=O)OC(C)(C)C)CC3)C(=O)[C@@H]3CCCC[C@H]23)cc1OC.Cl>>COc1ccc(C2=NN(C3CCN(C(=O)[C@@H](N)Cn4cccn4)CC3)C(=O)[C@@H]3CCCC[C@H]23)cc1OC.Cl | null | C1COCCO1 | null | null | null | train |
US20090062348A1 | COCc1ccc(C(=O)NCc2cc3ccc(O)cc3o2)c(N)n1.OCc1ccccn1>>COCc1ccc(C(=O)NCc2cc3ccc(OCc4ccccn4)cc3o2)c(N)n1 | null | C1CCOC1 | null | CCOC(=O)/N=N/C(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | train |
US20090221555A1 | CNC(=O)c1cccc(F)c1Nc1nc(Nc2ccc3c(c2)NC(=O)CNC3)ncc1Cl.FC(F)(F)CCI>>CNC(=O)c1cccc(F)c1Nc1nc(Nc2ccc3c(c2)NC(=O)CN(CCC(F)(F)F)C3)ncc1Cl | null | CCCCO | null | O=C([O-])[O-].[K+].[K+] | null | train |
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