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 |
|---|---|---|---|---|---|---|---|
US05756817 | N.O=C(N[C@H](CO)Cc1cccc(F)c1)OCc1ccccc1.O=C(n1ccnc1)n1ccnc1>>NC(=O)OC[C@H](Cc1cccc(F)c1)NC(=O)OCc1ccccc1 | null | C1CCOC1 | null | O | null | train |
US20120010191A1 | CC(=O)OCc1c(Br)cccc1N1CCn2c(cc3c2CC(C)(C)C3)C1=O.CCN1CCN(c2ccc(Nc3cc(B4OC(C)(C)C(C)(C)O4)cn(C)c3=O)nc2)CC1>>CCN1CCN(c2ccc(Nc3cc(-c4cccc(N5CCn6c(cc7c6CC(C)(C)C7)C5=O)c4COC(C)=O)cn(C)c3=O)nc2)CC1 | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | ClCCl | null | COCCOC | O=C([O-])[O-].[Na+].[Na+] | train |
US20110046171A1 | Clc1cc(Br)cc(OCc2ccccc2)c1.O=S(=O)(Cl)Cl>>O=S(=O)(Cl)c1cc(Cl)cc(OCc2ccccc2)c1 | null | C1CCOC1 | null | null | null | train |
US20070161627A1 | COc1ccc2nccc(CCN3CCN(N=O)CC3)c2n1>>COc1ccc2nccc(CCN3CCN(N)CC3)c2n1 | null | C1CCOC1 | null | [Al+3].[H-].[H-].[H-].[H-].[Li+] | null | train |
US20130344030A1 | CC(O)C1(C(=O)OCc2ccccc2)COC(C)(C)CO1.O=S(=O)(N(c1ccc(Cl)cn1)S(=O)(=O)C(F)(F)F)C(F)(F)F>>CC(OS(=O)(=O)C(F)(F)F)C1(C(=O)OCc2ccccc2)COC(C)(C)CO1 | null | C1CCOC1 | null | [H-].[Na+] | [Cl-].[NH4+] | train |
US20100160303A1 | COc1ccc(C(=O)O)c(N)c1.N=CN>>COc1ccc2c(O)ncnc2c1 | null | COCCO | null | CC(=O)O | null | train |
US20060276533A1 | COC(=O)[C@@H](N=C=O)C(C)C.C[C@@H]1CC[C@@H](C(=O)N(c2cc(C3=CCCCC3)sc2C(=O)O)[C@@H]2CC[C@@H](O)CC2)CC1>>COC(=O)C(NC(=O)O[C@@H]1CC[C@@H](N(C(=O)[C@@H]2CC[C@@H](C)CC2)c2cc(C3=CCCCC3)sc2C(=O)O)CC1)C(C)C | null | Cc1ccccc1 | null | O | null | train |
US20100256133A1 | COc1ccncc1.NOc1ccc([N+](=O)[O-])cc1[N+](=O)[O-]>>COc1cc[n+](N)cc1.O=[N+]([O-])c1ccc([O-])c([N+](=O)[O-])c1 | null | CC#N | null | CCOCC | null | train |
US20070010556A1 | CCOC(=O)c1nc(C)sc1N.O=C=NC(=O)C(Cl)(Cl)Cl>>CCOC(=O)c1ncsc1NC(=O)NC(=O)C(Cl)(Cl)Cl | null | C1CCOC1 | null | null | null | train |
US20090306102A1 | Cc1cccc(C(=O)O)n1.O=S(Cl)Cl>>Cc1cccc(C(=O)Cl)n1 | null | ClCCl | null | null | null | train |
US20150111887A1 | CC(C)(C)[S@@](N)=O.Cn1cc(-c2cc3c(N4CCN(c5ncc(C(=O)c6ccc(F)cc6)cn5)CC4)ncnn3c2)cn1>>Cn1cc(-c2cc3c(N4CCN(c5ncc(/C(=N\[S@@](=O)C(C)(C)C)c6ccc(F)cc6)cn5)CC4)ncnn3c2)cn1 | null | C1CCOC1 | null | O | null | train |
US20150368245A1 | CC(C)(C)OC(=O)N(C[C@@H]1CC[C@@H](N2CNC(=O)c3cnc4c(ccn4COCC[Si](C)(C)C)c32)CC1)CC(F)(F)F.COCCBr>>COCCN1CN([C@@H]2CC[C@@H](CN(CC(F)(F)F)C(=O)OC(C)(C)C)CC2)c2c(cnc3c2ccn3COCC[Si](C)(C)C)C1=O | null | CN(C)C=O | null | O | [H-].[Na+] | train |
US20110105463A1 | BrBr.CCOC(=O)C1CCOc2cc(O)c(Cl)cc21>>CCOC(=O)C1CCOc2c1cc(Cl)c(O)c2Br | null | CC(=O)O | null | null | null | train |
US20090143367A1 | Cc1nc(Br)n2c1c(C)nc1ccc(F)cc12.OB(O)c1ccc(F)cc1F>>Cc1nc(-c2ccc(F)cc2F)n2c1c(C)nc1ccc(F)cc12 | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | null | null | O=C([O-])[O-].[K+].[K+] | null | train |
US08987474B2 | CC(C)NS(=O)(=O)c1ccc2c(c1)CC(=O)N2.CN(C)C=O.COC(OC)N(C)C>>CN(C)C=C1C(=O)Nc2ccc(S(=O)(=O)O)cc21 | null | CN(C)C=O | null | O | null | train |
US20090275537A1 | CI.COC(=O)C(F)(F)C[C@@H](COC(=O)OC(C)(C)C)NC(=O)OC(C)(C)C>>COC(=O)C(F)(F)C[C@@H](COC(=O)OC(C)(C)C)N(C)C(=O)OC(C)(C)C | null | CN(C)C=O | null | [H-].[Na+] | null | train |
US05728899 | CC(=O)O[C@H]1C=C[C@@H](O)C1>>CC(=O)O[C@@H]1CC[C@H](O)C1 | [Ni] | CCO | null | CCN(CC)CC | null | train |
US20030171418A1 | C=CCc1c(OC(C)=O)ccc2cn[nH]c12.CCN=C=O>>C=CCc1c(OC(C)=O)ccc2cnn(C(=O)NCC)c12 | null | C1CCOC1 | null | null | null | train |
US03956314 | CCOC(=O)C(c1ccccc1)C(CN)c1ccc(Cl)cc1>>O=C1NCC(c2ccc(Cl)cc2)C1c1ccccc1 | null | Cc1ccccc1 | null | CCO | null | train |
US20090221555A1 | CCN1CCc2ccc(N)cc2CC1.O=C1NCCCCC1Nc1nc(Cl)ncc1Cl>>CCN1CCc2ccc(Nc3ncc(Cl)c(NC4CCCCNC4=O)n3)cc2CC1 | null | CC(C)O | O | Cl | [Na] | train |
US20040116328A1 | CC#CCn1c(N2CCN(C(=O)OC(C)(C)C)CC2)nc2cnn(C)c(=O)c21>>CC#CCn1c(N2CCNCC2)nc2cnn(C)c(=O)c21 | null | ClCCl | null | O=C(O)C(F)(F)F | null | train |
US20090137580A1 | CCOC(=O)Cc1ccc(O)cc1.Cn1ccc2ncnc(Cl)c21>>CCOC(=O)Cc1ccc(Oc2ncnc3ccn(C)c23)cc1 | null | O | null | CN1CCCC1=O | O=C([O-])[O-].[K+].[K+] | train |
US20140329858A1 | COc1ccc(CN2C(=O)N(C)[C@@H]3CC(O)(c4ccccc4)CC[C@H]32)cc1>>CN1C(=O)N[C@@H]2CCC(c3ccccc3)=C[C@H]21 | null | O=C(O)C(F)(F)F | null | null | null | train |
US04948796 | O=[N+]([O-])c1ccc2c(c1)C(N1CCN(C/C=C/c3cccc(NC(c4ccccc4)(c4ccccc4)c4ccccc4)c3)CC1)c1ccccc1CC2>>Nc1cccc(/C=C/CN2CCN(C3c4ccccc4CCc4ccc([N+](=O)[O-])cc43)CC2)c1 | null | CC(=O)O | CO | null | null | train |
US20130150353A1 | CC1(C)OB(c2cnc3ccc(F)cc3c2)OC1(C)C.C[Si](C)(C)CCOCN(COCC[Si](C)(C)C)c1cc(Cl)nc2c(I)cnn12>>C[Si](C)(C)CCOCN(COCC[Si](C)(C)C)c1cc(Cl)nc2c(-c3cnc4ccc(F)cc4c3)cnn12 | null | C1COCCO1 | O | O=P([O-])([O-])[O-].[K+].[K+].[K+] | null | train |
US06265415B1 | Cc1cccc(C)c1CCl.Cc1nc2c(O)cccn2c1CO>>Cc1cccc(C)c1COc1cccn2c(CO)c(C)nc12 | null | CC(C)=O | null | [I-].[Na+] | null | train |
US20060142357A1 | CC(C)(C)OC(=O)N1CCC(CBr)CC1.CC1SC(N[C@H]2CC3CCC2C3)=NC1=O>>CC(C)(C)OC(=O)N1CCC(CC2(C)SC(N[C@H]3CC4CCC3C4)=NC2=O)CC1 | null | C1CCOC1 | null | CC(C)[N-]C(C)C.[Li+] | null | train |
US20120142717A1 | O=Cc1ccc(Oc2ccc(F)cc2)cc1>>OCc1ccc(Oc2ccc(F)cc2)cc1 | null | CO | null | [BH4-].[Na+] | null | train |
US20080220031A1 | CC1(C)CC(N)CC(C)(C)N1.CCCCCCC=CC1CC(=O)OC1=O>>CCCCCCC=CC1CC(=O)N(C2CC(C)(C)NC(C)(C)C2)C1=O | null | CC(=O)O | null | null | null | train |
US20030073840A1 | CC[C@]1(c2ccnc(OC)c2COCOC)OC1CO>>CC[C@@](O)(CCO)c1ccnc(OC)c1COCOC | null | CCOCC | null | [Al+3].[H-].[H-].[H-].[H-].[Li+] | null | train |
US06613913B2 | CC=Cc1c(N)ccc2c1O[C@@H](COS(=O)(=O)c1ccc(C)cc1)CO2.O=C(Cl)OCc1ccccc1>>CC=CC1(COS(=O)(=O)c2ccc(C)cc2)COc2ccc(NC(=O)OCc3ccccc3)cc2O1 | null | CCOC(C)=O | null | CCN(C(C)C)C(C)C | null | train |
US20160083366A1 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.Nc1ccc(Cl)c(O)c1>>CC(C)(C)OC(=O)Nc1ccc(Cl)c(O)c1 | null | C1CCOC1 | CCOC(C)=O | null | null | train |
US20120035053A1 | CC(C)(C)C(=O)Cl.Cc1cc(C)c(C2C(=O)CC(CC3CCOC3)CC2=O)c(C)c1>>Cc1cc(C)c(C2=C(OC(=O)C(C)(C)C)CC(CC3CCOC3)CC2=O)c(C)c1 | null | ClCCl | null | CCN(CC)CC | null | train |
US20070275952A1 | CC(C)(C)OC(=O)N1CCN(c2ncccc2OCc2ccncc2)CC1.O=C(O)C(F)(F)F>>O=C(O)C(F)(F)F.c1cnc(N2CCNCC2)c(OCc2ccncc2)c1 | null | ClCCl | null | null | null | train |
US20020137929A1 | O=C1C2=C(CCCC2)C(=O)N1c1cc([N+](=O)[O-])c(Cl)cc1F>>Nc1cc(N2C(=O)C3=C(CCCC3)C2=O)c(F)cc1Cl | [Fe] | CC(=O)O | null | null | null | train |
US20080161419A1 | NC(N)=NC(=O)c1ccc2c(c1)C(=O)c1c(CO)cccc1-2.NO>>NC(N)=NC(=O)c1ccc2c(c1)C(=NO)c1c(CO)cccc1-2 | null | c1ccncc1 | null | Cl | null | train |
US20020022605A1 | CS(=O)(=O)Nc1cc(C(O)CN(Cc2ccccc2)Cc2ccccc2)ccc1OCc1ccccc1>>CS(=O)(=O)Nc1cc(C(O)CN)ccc1O | [Pd] | CO | null | null | null | train |
US20130116263A1 | COC(=O)Cc1cc(C)c([N+](=O)[O-])cc1Cl>>COC(=O)Cc1cc(C)c(N)cc1Cl | null | CO | null | [BH4-].[Na+] | null | train |
US06589950B1 | Clc1nc(Cl)c2[nH]cnc2n1.NC1CCC1>>Clc1nc(NC2CCC2)c2[nH]cnc2n1 | null | CCCCO | null | CCN(C(C)C)C(C)C | null | train |
US06054448 | CCOP(=O)(CCC(c1ccccc1)c1ccccc1)OCC.CSSC>>CCOP(=O)(OCC)C(CC(c1ccccc1)c1ccccc1)SC | null | C1CCOC1 | null | O | [Li]CCCC | train |
US20120322801A1 | O=C1OCCC1Br.OCCCS>>O=C1OCCC1SCCCO | null | CN(C)C=O | null | CCN(C(C)C)C(C)C | null | train |
US20080070928A1 | FC(F)(F)c1ccc(Br)cn1.Oc1cc2[nH]c(-c3cnccn3)nc2cc1Oc1ccccc1F>>Fc1ccccc1Oc1cc2nc(-c3cnccn3)[nH]c2cc1Oc1ccc(C(F)(F)F)nc1 | O=[Cu] | CN1CCCC1=O | null | O=C([O-])[O-].[Cs+].[Cs+] | null | train |
US20120261651A1 | Nc1nc2ccccc2c2ccccc12.O=CCCl>>c1ccc2c(c1)c1ccccc1n1ccnc21 | null | CC(C)O | null | O=C([O-])[O-].[Na+].[Na+] | null | train |
US06326506B1 | C=Cc1ccccc1.C[SiH](Cl)Cl>>Cl[SiH](Cl)CCCc1ccccc1 | [Pt] | Cc1ccccc1 | null | null | null | train |
US06034087 | CC(=O)OC(C)=O.COC1CCC(CO)CO1>>COC1CCC(COC(C)=O)CO1 | null | c1ccncc1 | null | null | null | train |
US20120283271A1 | COC(=O)[C@H](CCSC)N1Cc2c(cccc2C(F)(F)F)C1=O>>CSCC[C@@H](C(=O)O)N1Cc2c(cccc2C(F)(F)F)C1=O | null | C1CCOC1 | O | [Li+].[OH-] | null | train |
US20150038488A1 | COc1ccc([C@@H](C)N2C[C@H]([C@@H](C)O)CC2=O)cc1.CS(=O)(=O)c1nc(Cl)cc2ncn(C(F)F)c12>>COc1ccc([C@@H](C)N2C[C@H]([C@@H](C)Oc3nc(Cl)cc4ncn(C(F)F)c34)CC2=O)cc1 | null | CN(C)C=O | null | C[Si](C)(C)[N-][Si](C)(C)C.[Na+] | null | train |
US20090286816A1 | Cc1nc(Br)ccc1[N+](=O)[O-].c1nc[nH]n1>>Cc1nc(-n2cncn2)ccc1[N+](=O)[O-] | null | CS(C)=O | null | O=C([O-])[O-].[K+].[K+] | null | train |
US20090137595A1 | CC(C)C(=O)Nc1cn2nc(I)ccc2n1.Nc1cccc(O)c1>>CC(C)C(=O)Nc1cn2nc(Oc3cccc(N)c3)ccc2n1 | null | CN(C)C=O | null | O=C([O-])[O-].[K+].[K+] | null | train |
US20120295885A1 | CC(C)(C)c1cc(F)c2c(=O)n(-c3cccc(-n4cc(C#N)c(Nc5ccc(C(C)(C)O)cc5)n4)c3C=O)ncc2c1.O>>CC(C)(C)c1cc(F)c2c(=O)n(-c3cccc(-n4cc(C(N)=O)c(Nc5ccc(C(C)(C)O)cc5)n4)c3C=O)ncc2c1 | null | O | null | C1CCOC1 | null | train |
US20100144741A1 | CC(C)c1cccc(C2(NC[C@@H](O)[C@H](Cc3ccc([N+](=O)[O-])cc3)NC(=O)OC(C)(C)C)CC2)c1.O=C(n1ccnc1)n1ccnc1>>CC(C)c1cccc(C2(N3C[C@H]([C@H](Cc4ccc([N+](=O)[O-])cc4)NC(=O)OC(C)(C)C)OC3=O)CC2)c1 | CN(C)c1ccncc1 | ClCCCl | null | CCN(C(C)C)C(C)C | null | train |
US20020143023A1 | CCOC(=O)N1C(=O)NC(C)=C(C(=O)O)C1c1cccc(Cl)c1.NCCC(c1ccccc1)c1ccccc1>>CCOC(=O)N1C(=O)NC(C)=C(C(=O)NCCC(c2ccccc2)c2ccccc2)C1c1cccc(Cl)c1 | null | ClCCl | null | CCN=C=NCCCN(C)C | Cl | train |
US20040204320A1 | CCOC(=O)c1ccc(Br)c(OCC(=O)CC)c1Br>>CCC(=O)COc1c(Br)ccc(C(=O)O)c1Br | null | C1CCOC1 | O | [Na+].[OH-] | null | train |
US20130317026A1 | CCOC(=O)c1cc(O)nc2c1cnn2C(C)C.NC(=O)CCC(=O)NCl>>CCOC(=O)c1c(Cl)c(O)nc2c1cnn2C(C)C | null | CN(C)C=O | null | CCOC(C)=O | O | train |
US20130331372A1 | COC(=O)CCc1ccc(Cl)cc1.II>>COC(=O)CCc1ccc(Cl)c(I)c1 | null | O=S(=O)(O)O | null | [Na+].[O-][I+3]([O-])([O-])[O-] | null | train |
US20080312293A1 | CS(N)(=O)=O.C[C@@H](C(=O)O)c1cccc(C(=O)C2CCCC2)c1>>C[C@@H](C(=O)NS(C)(=O)=O)c1cccc(C(=O)C2CCCC2)c1 | null | ClCCl | null | C1CCC2=NCCCN2CC1 | O=C(n1ccnc1)n1ccnc1 | train |
US20140350019A1 | CCOC(=O)COc1ccc(F)c(NCc2c(F)ccc(-c3cccc(F)c3)c2F)c1F>>O=C(O)COc1ccc(F)c(NCc2c(F)ccc(-c3cccc(F)c3)c2F)c1F | null | C1CCOC1 | null | [Na+].[OH-] | null | train |
US05246948 | NCCCOc1ccncc1.O=C(Cl)c1cccs1>>O=C(NCCCOc1ccncc1)c1cccs1 | null | ClCCl | null | CCN(CC)CC | null | train |
US07250518B2 | BrCCBr.COC(=O)Cc1ccc(C#N)c(F)c1>>COC(=O)C1(c2ccc(C#N)c(F)c2)CC1 | null | C1CCOC1 | null | [H-].[Na+] | null | train |
US20050010031A1 | BrCCBr.C=CC[C@H](NS(=O)(=O)c1ccccc1[N+](=O)[O-])C(=O)N[C@@H](Cc1ccc2ccccc2c1)C(=O)OC>>C=CC[C@H]1C(=O)N([C@@H](Cc2ccc3ccccc3c2)C(=O)OC)CCN1S(=O)(=O)c1ccccc1[N+](=O)[O-] | null | CN(C)C=O | null | O=C([O-])[O-].[K+].[K+] | null | train |
US06245790B1 | COC(=O)c1cccc(CC2=C(c3nc(-c4ccccc4)c(-c4ccccc4)o3)C3CCC2C3)c1>>O=C(O)c1cccc(CC2=C(c3nc(-c4ccccc4)c(-c4ccccc4)o3)C3CCC2C3)c1 | null | C1CCOC1 | CO | [Na+].[OH-] | null | train |
US20120088750A1 | CCNC(=O)Nc1nc2cc(OCc3ccccc3)cc(C=O)c2s1.CON>>CCNC(=O)Nc1nc2cc(OCc3ccccc3)cc(/C=N/OC)c2s1 | null | CN(C)C=O | null | CCN(C(C)C)C(C)C | Cl | train |
US20140275076A1 | O=C1CCN(c2ccccc2)CC1.O=S(=O)(N(c1ccccc1)S(=O)(=O)C(F)(F)F)C(F)(F)F>>O=S(=O)(OC1=CCN(c2ccccc2)CC1)C(F)(F)F | null | C1CCOC1 | null | C[Si](C)(C)[N-][Si](C)(C)C.[Li+] | null | train |
US20110237832A1 | COC(c1ccc(N(C)C)cc1)[C@H](C)/C=C/C=C/C(=O)O.ClCCl>>CC(/C=C/C(=O)O)=C\[C@@H](C)C(=O)c1ccc(N(C)C)cc1 | null | ClCCl | O | N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O | null | train |
US20140306146A1 | C=CCCO.CS(=O)(=O)Cl>>C=CCCOS(C)(=O)=O | null | C1CCOC1 | CCN(CC)CC | Cl | null | train |
US20100280088A1 | CCC(C#N)OS(C)(=O)=O.O=Cc1cccc(O)c1Cl>>CCC(C#N)Oc1cccc(C=O)c1Cl | null | CN1CCCC1=O | O | [I-].[K+] | O=C([O-])[O-].[Cs+].[Cs+] | train |
US20080004302A1 | COc1cc(N)[nH]n1.Cc1cc(CNc2nccc(Cl)n2)on1>>COc1cc(Nc2ccnc(NCc3cc(C)no3)n2)[nH]n1 | null | CCO | null | null | null | train |
US20020143034A1 | OC[C@H](Cc1ccc(Oc2ccnc3ccccc23)cc1)N(Cc1ccccc1)C[C@H](O)c1cccc(Cl)c1>>OCC(Cc1ccc(Oc2ccnc3ccccc23)cc1)NC[C@H](O)c1cccc(Cl)c1 | [Pd] | Clc1ccccc1 | null | CO | null | train |
US20160115126A1 | C[Si](C)(C)CCOCCl.Cc1c[nH]c2c(Br)ccc(Br)c12>>Cc1cn(COCC[Si](C)(C)C)c2c(Br)ccc(Br)c12 | null | C1CCOC1 | null | O | [H-].[Na+] | train |
US20140294898A1 | O=C(Cl)OCC1c2ccccc2-c2ccccc21.O=C(O)[C@@H]1C[C@@H](OCc2ccccc2)CN1>>O=C(O)[C@@H]1C[C@@H](OCc2ccccc2)CN1C(=O)OCC1c2ccccc2-c2ccccc21 | null | C1COCCO1 | O | O=C(O)C(F)(F)F | O=C([O-])[O-].[K+].[K+] | train |
US04820834 | CN1C(=O)C(N)N=C(c2ccccc2)c2ccccc21.O=C=Nc1ccc(Cl)c(Cl)c1>>CN1C(=O)C(NC(=O)Nc2ccc(Cl)c(Cl)c2)N=C(c2ccccc2)c2ccccc21 | null | C1CCOC1 | null | null | null | train |
US20140179690A1 | NC1=N[C@@]2(c3cccc(F)c3F)CO[C@H](C(F)F)[C@H]2CS1.O=[N+]([O-])O>>NC1=N[C@@]2(c3cc([N+](=O)[O-])cc(F)c3F)CO[C@H](C(F)F)[C@H]2CS1 | null | O=C(O)C(F)(F)F | null | O=S(=O)(O)O | O=C([O-])O.[Na+] | train |
US20090069300A1 | C1CCNC1.O=CCN1CCc2cc(Br)ccc2C1=O>>O=C1c2ccc(Br)cc2CCN1CCN1CCCC1 | null | CO | ClCCl | CC(=O)O | [BH3-]C#N.[Na+] | train |
US20040180884A1 | BrCc1ccc2c(n1)CCCC2.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>[Br-].c1ccc([P+](Cc2ccc3c(n2)CCCC3)(c2ccccc2)c2ccccc2)cc1 | null | CC#N | null | null | null | train |
US20140343092A1 | CN.Cc1c(-c2c(CO[Si](C)(C)C(C)(C)C)oc(=O)c3sc4c(c23)CCCC4)ccc2c1CCCO2>>Cc1c(-c2c(CO)n(C)c(=O)c3sc4c(c23)CCCC4)ccc2c1CCCO2 | null | CCO | null | null | null | train |
US04186199 | O=C(Nc1ccccc1N1CCc2cc(Cl)ccc21)c1ccccc1.O=P(Cl)(Cl)Cl>>Cl.Clc1cc2c3c(c1)C(c1ccccc1)=Nc1ccccc1N3CC2 | null | ClCCl | null | null | null | train |
US20140200206A1 | CC(C)(O)Cn1cc([N+](=O)[O-])cn1.C[Si](C)(C)Cl>>CC(C)(Cn1cc([N+](=O)[O-])cn1)O[Si](C)(C)C | null | CCOC(C)=O | CN(C)C=O | c1c[nH]cn1 | null | train |
US20150158851A1 | CCOC(=O)C1CCC2(CC1)OCCO2.COC(=O)OC>>CCOC(=O)C1(C(=O)OC)CCC2(CC1)OCCO2 | null | C1CCOC1 | null | CC(C)[N-]C(C)C.[Li+] | null | train |
US20150152096A1 | CCOC(=O)CC(C)=O.NC(N)=O.O=Cc1ccc(F)cc1Br>>CCOC(=O)C1=C(C)NC(=O)NC1c1ccc(F)cc1Br | null | CC#N | null | C[Si](C)(C)Cl | [I-].[Na+] | train |
US20150126522A1 | CO.Cc1c(C(=O)O)cc(Cl)cc1[N+](=O)[O-]>>COC(=O)c1cc(Cl)cc([N+](=O)[O-])c1C | null | CCOC(C)=O | null | O=S(Cl)Cl | null | train |
US06232290B1 | COCCCCCCOc1ccc(-c2nnc(-c3ccc(C(=O)O)cc3)s2)cc1.On1nnc2ccccc21>>COCCCCCCOc1ccc(-c2nnc(-c3ccc(C(=O)On4nnc5ccccc54)cc3)s2)cc1 | null | ClCCl | null | CCN=C=NCCCN(C)C | Cl | train |
US20140194469A1 | CC(=O)Cc1ccccc1.COC(OC)N(C)C>>CC(=O)/C(=C/N(C)C)c1ccccc1 | null | CN(C)C=O | null | null | null | train |
US20140088079A1 | COc1ccc(Cc2cc(C3O[C@H](COCc4ccccc4)[C@@H](OCc4ccccc4)[C@H](OCc4ccccc4)[C@H]3OCc3ccccc3)c3c(c2Cl)CCO3)cc1>>COc1ccc(Cc2cc([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c3c(c2Cl)CCO3)cc1 | [Pd] | C1CCOC1 | CO | null | null | train |
US20100298402A1 | CC(=O)Oc1ccc(C(=Cc2ccc(F)c(C)c2)C(=O)O)cc1>>Cc1cc(C=C(C(=O)O)c2ccc(O)cc2)ccc1F | null | CO | O | [Na+].[OH-] | null | train |
US20050059669A1 | Brc1ncccn1.COC(=O)c1cc(N2CCC(N)CC2)ccc1F>>COC(=O)c1cc(N2CCC(Nc3ncccn3)CC2)ccc1F | null | O | null | CCN(C(C)C)C(C)C | CS(C)=O | train |
US20110257151A1 | CC1(C)Cc2cc(C(=O)O)ccc2NC1c1cc(Cl)cc(N2CCOCC2)c1.CS(N)(=O)=O>>CC1(C)Cc2cc(C(=O)NS(C)(=O)=O)ccc2NC1c1cc(Cl)cc(N2CCOCC2)c1 | CN(C)c1ccncc1 | ClCCl | null | CCN=C=NCCCN(C)C | Cl | train |
US20160221998A1 | CC1=C(c2cncnc2)C(=O)N(C(C)(C)C(=O)Cl)CO1.Nc1cccc(Cl)n1>>CC1=C(c2cncnc2)C(=O)N(C(C)(C)C(=O)Nc2cccc(Cl)n2)CO1 | null | O | null | CCN(CC)CC | ClCCl | train |
US20110144092A1 | CCI.CCOC(=O)N1CCc2nc(-c3ccncn3)cc(=O)n2CC1>>CCOC(=O)N1CCn2c(nc(-c3ccncn3)cc2=O)C(CC)C1 | null | C1CCOC1 | null | C[Si](C)(C)[N-][Si](C)(C)C.[Li+] | null | train |
US20080021032A1 | Cc1ccc2sccc2c1.O=C1CCC(=O)N1Br>>BrCc1ccc2sccc2c1 | null | ClC(Cl)(Cl)Cl | null | O=C(OOC(=O)c1ccccc1)c1ccccc1 | null | train |
US20100286116A1 | CC(C)N.COC(=O)c1sc(/C=C/c2c(-c3ccccc3)noc2C)nc1C>>Cc1nc(/C=C/c2c(-c3ccccc3)noc2C)sc1C(=O)NC(C)C | null | C1COCCO1 | Cc1ccccc1 | C[Al](C)C | null | train |
US05075303 | Cc1ccnc2c1CCCC2S(=O)c1ccccc1>>Cc1ccnc2c1CCC=C2 | null | Cc1ccccc1 | null | null | null | train |
US05958910 | NC(N)=S.O=C(CBr)c1cc(F)cc(C(F)(F)F)c1>>Br.Nc1nc(-c2cc(F)cc(C(F)(F)F)c2)cs1 | null | CO | null | null | null | train |
US20140323504A1 | C=CC(=O)Cl.Cn1cc(Nc2cc3c(cn2)cnn3Cc2cccc(N)c2)cn1>>C=CC(=O)Nc1cccc(Cn2ncc3cnc(Nc4cnn(C)c4)cc32)c1 | null | CN(C)C=O | ClCCl | CCN(C(C)C)C(C)C | null | train |
US20120029190A1 | NC1CCCN(C(=O)OCc2ccccc2)CC1O.O=C(O)c1ccccn1>>O=C(NC1CCCN(C(=O)OCc2ccccc2)CC1O)c1ccccn1 | null | ClCCl | null | CCN=C=NCCCN(C)C | On1nnc2ccccc21 | train |
US05629325 | CC(C)(C)OC(=O)N1CCC[C@H]1CO.Oc1cnc(F)c(Br)c1>>CC(C)(C)OC(=O)N1CCC[C@H]1COc1cnc(F)c(Br)c1 | null | C1CCOC1 | null | CCOC(=O)/N=N/C(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | train |
US20100197683A1 | CCCc1c(Cc2ccc(-c3ccccc3C#N)cc2)c(=O)n(CC(OC)C(C)(C)C)c2nc(C)nn12.O=C([O-])O.[NH3+]O>>CCCc1c(Cc2ccc(-c3ccccc3-c3noc(=O)[nH]3)cc2)c(=O)n(CC(OC)C(C)(C)C)c2nc(C)nn12 | null | CCOC(C)=O | null | CS(C)=O | [Cl-].[Na+] | train |
US20090306082A1 | COC(=O)c1ccc(OC2CCCC2)c2oc(C)cc12.O=C1CCC(=O)N1Br>>COC(=O)c1ccc(OC2CCCC2)c2oc(CBr)cc12 | null | ClC(Cl)(Cl)Cl | null | CC(C)(C#N)N=NC(C)(C)C#N | null | train |
US05106976 | O=C(OO)c1cccc(Cl)c1.c1ccc(CSc2cnc3ccccc3n2)nc1>>O=S(Cc1ccccn1)c1cnc2ccccc2n1 | null | CO | ClC(Cl)Cl | Cl | O=C([O-])O.[Na+] | train |
US20090005371A1 | CC(C)(C)[Si](C)(C)Cl.O=[N+]([O-])c1cnc2cc(OCc3ccccc3)ccc2c1NCCO>>CC(C)(C)[Si](C)(C)OCCNc1c([N+](=O)[O-])cnc2cc(OCc3ccccc3)ccc12 | CN(C)c1ccncc1 | CCOC(C)=O | null | c1ccncc1 | null | train |
US20030229094A1 | CC(C)Br.O=[N+]([O-])c1ccccc1O>>CC(C)Oc1ccccc1[N+](=O)[O-] | null | CC(C)=O | CN(C)C=O | O=C([O-])[O-].[K+].[K+] | null | train |
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