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 |
|---|---|---|---|---|---|---|---|
US20160251339A1 | COc1ccc(S(=O)(=O)n2cc(C(F)F)c3ccc(C(F)(F)F)cc32)cc1N1CCN(C(=O)C(Cl)(Cl)Cl)CC1>>COc1ccc(S(=O)(=O)n2cc(C(F)F)c3ccc(C(F)(F)F)cc32)cc1N1CCNCC1 | null | C1CCOC1 | null | [K+].[OH-] | null | train |
US20100204274A1 | CC(NC(=O)c1ccccc1)C(C)C(=O)O.CC1(C)CNCC[C@]1(O)c1ccc(Cl)cc1>>CC(NC(=O)c1ccccc1)C(C)C(=O)N1CC[C@](O)(c2ccc(Cl)cc2)C(C)(C)C1 | null | C1CCOC1 | null | CCN(C(C)C)C(C)C | CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.F[P-](F)(F)(F)(F)F | train |
US05663448 | BrBr.CC(=O)Nc1ccc(C(C)(C)C)cc1>>CC(=O)Nc1ccc(C(C)(C)C)cc1Br | null | CC(=O)O | null | null | null | train |
US20130197271A1 | ClC(c1ccccc1)(c1ccccc1)c1ccccc1.OCCOCCOCCO>>OCCOCCOCCOC(c1ccccc1)(c1ccccc1)c1ccccc1 | null | ClCCl | null | CCN(CC)CC | null | train |
US20090215843A1 | CCOC(=O)CCCCC(CCc1ccc(C#N)cc1)C(=O)O>>CCOC(=O)CCCCC(CO)CCc1ccc(C#N)cc1 | null | C1CCOC1 | null | O=C([O-])O.[Na+] | null | train |
US20110319379A1 | CCOC(=O)c1cc(O)c2cn(C)nc2c1.O=S(=O)(N(c1ccccc1)S(=O)(=O)C(F)(F)F)C(F)(F)F>>CCOC(=O)c1cc(OS(=O)(=O)C(F)(F)F)c2cn(C)nc2c1 | null | ClCCl | null | CCN(C(C)C)C(C)C | null | train |
US05420151 | CCCN(CCC)C1COc2cccc(N)c2C1.COC1CCC(OC)O1>>CCCN(CCC)C1COc2cccc(-n3cccc3)c2C1 | null | CC(=O)O | null | [Na+].[OH-] | null | train |
US04528028 | O=C(O)CC[C@@H](CF)N=Cc1cc(Cl)ccc1O>>O=C(O)CC[C@@H](CF)NCc1cc(Cl)ccc1O | null | CCO | null | O | [BH4-].[Na+] | train |
US20020103229A1 | N#Cc1ccc2c(c1)c(/C=C/c1ccccc1)nn2C1CCCCO1>>N#Cc1ccc2c(c1)c(CCc1ccccc1)nn2C1CCCCO1 | null | CCOC(C)=O | null | null | null | train |
US20070281933A1 | CC(C)(C)OC(=O)N1CCC(c2n[nH]c3c(C(N)=O)cc(Br)cc23)CC1.OB(O)c1cccnc1>>CC(C)(C)OC(=O)N1CCC(c2n[nH]c3c(C(N)=O)cc(-c4cccnc4)cc23)CC1 | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | C1COCCO1 | O | O=C([O-])[O-].[K+].[K+] | null | train |
US05281590 | CCS(=O)(=O)CCC(=O)NNC(=O)N1Cc2ccc(OC)cc2Oc2ccc(Cl)cc21>>CCS(=O)(=O)CCC(=O)NNC(=O)N1Cc2ccc(O)cc2Oc2ccc(Cl)cc21 | null | ClCCl | null | BrB(Br)Br | null | train |
US20120208798A1 | CC(C)(C)OC(=O)Cn1cnc(-c2ccc([N+](=O)[O-])cc2)c1>>CC(C)(C)OC(=O)Cn1cnc(-c2ccc(N)cc2)c1 | [Pd] | CCO | null | O=C[O-].[NH4+] | null | train |
US05589474 | O=C1Nc2ccccc2Sc2ccccc21.S=P12SP3(=S)SP(=S)(S1)SP(=S)(S2)S3>>S=C1Nc2ccccc2Sc2ccccc21 | null | c1ccncc1 | null | Cl | null | train |
US20080306055A1 | CNOC.COC(=O)c1ccc(OC)nc1>>COc1ccc(C(=O)N(C)OC)cn1 | null | C1CCOC1 | null | CC(C)[Mg]Cl | Cl | train |
US20100016279A1 | O=C(OCc1ccccc1)N1CC=C(c2ccc(O)cc2)CC1>>Oc1ccc(C2CCNCC2)cc1 | [Pd] | CO | null | null | null | train |
US20110077273A1 | BrCC1CCCCC1.Fc1cc2nc(-c3cccnc3Cl)[nH]c2cc1F>>Fc1cc2nc(-c3cccnc3Cl)n(CC3CCCCC3)c2cc1F | null | CN(C)C=O | null | [H-].[Na+] | null | train |
US20020094989A1 | CC(C)(C)OC(=O)N1CCC(C=CC(=O)c2cccnc2)CC1>>CC(C)(C)OC(=O)N1CCC(CCC(=O)c2cccnc2)CC1 | [Pd] | CCO | null | null | null | train |
US20160176866A1 | Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2c(N)nc(Nc3ccc(Br)cc3)nc21.OCCN1CCOCC1>>Cn1c(=O)c(-c2c(Cl)cccc2Cl)cc2c(N)nc(Nc3ccc(OCCN4CCOCC4)cc3)nc21 | I[Cu]I | O | null | O=C([O-])[O-].[Cs+].[Cs+] | null | train |
US04829074 | COC(=O)C(C)Br.c1nnn[nH]1>>COC(=O)C(C)n1cnnn1 | null | CC(C)=O | null | O=C([O-])[O-].[K+].[K+] | null | train |
US20070281933A1 | NC(=O)c1cc(-c2ccccc2)cc2c(C3CCNCC3)n[nH]c12.O=S(=O)(Cl)c1ccc(F)cc1>>NC(=O)c1cc(-c2ccccc2)cc2c(C3CCN(S(=O)(=O)c4ccc(F)cc4)CC3)n[nH]c12 | CN(C)c1ccncc1 | CN(C)C=O | null | CCN(CC)CC | Cl | train |
US20150045560A1 | CCCCC#Cc1c(NCCCCC)ccc2c(C#CCCCC)c(NCCCCC)ccc12>>CCCCCn1c(CCCC)cc2c3ccc4c(cc(CCCC)n4CCCCC)c3ccc21 | null | CS(C)=O | null | [K+].[OH-] | null | train |
US20050282862A1 | Clc1ccncc1.O=C(Nc1ccc(Cl)cn1)c1cc(Cl)ccc1NCC1CCNCC1>>O=C(Nc1ccc(Cl)cn1)c1cc(Cl)ccc1NCC1CCN(c2ccncc2)CC1 | null | CCO | null | CCN(CC)CC | Cl | train |
US04873236 | CCN(CC)CC1CCCCN1CCN.O=C1Nc2cccnc2N(C(=O)Cl)c2ccc(Cl)cc21>>CCN(CC)CC1CCCCN1CCNC(=O)N1c2ccc(Cl)cc2C(=O)Nc2cccnc21 | null | ClCCCl | null | null | null | train |
US05189045 | N#CC(Cc1cccc2c1OCO2)C(=O)O>>N#CCCc1cccc2c1OCO2 | null | O | null | CC(=O)N(C)C | null | train |
US04571396 | CCS.CCn1cc(C(=O)O)c(=O)c2cc(F)c(Cl)nc21>>CCSc1nc2c(cc1F)c(=O)c(C(=O)O)cn2CC | null | CCO | CN(C)C=O | Cl | [K+].[OH-] | train |
US20160024060A1 | Br.COCc1ccc(C(C)=O)c2sc(C(=O)Nc3ccc4c(CO)cccc4n3)c(C)c12>>Br.COCc1ccc(C(C)=O)c2sc(C(=O)Nc3ccc4c(CO)cccc4n3)c(C)c12 | null | CC#N | null | O | null | train |
US20100093730A1 | CCOC(=O)Cc1ccc(C(F)(F)F)cc1.N#CCBr>>CCOC(=O)C(CC#N)c1ccc(C(F)(F)F)cc1 | null | C1CCOC1 | null | C[Si](C)(C)[N-][Si](C)(C)C.[Li+] | null | train |
US20100152112A1 | Brc1ccc2nccc(-c3ccncc3)c2c1.CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C>>CC1(C)OB(c2ccc3nccc(-c4ccncc4)c3c2)OC1(C)C | null | C1COCCO1 | null | CC(=O)[O-].[K+] | null | train |
US05077304 | CC(C)c1cc(Oc2ccc(Cl)cc2)nc(C(C)C)c1NC(=S)NC(C)(C)C.CI>>CSC(=Nc1c(C(C)C)cc(Oc2ccc(Cl)cc2)nc1C(C)C)NC(C)(C)C | null | CCO | null | null | null | train |
US20110071128A1 | Cn1ncc(Cl)c1C(=O)O.Nc1cc2nc(-c3ccccc3)cn2c(N2CCOCC2)n1>>Cn1ncc(Cl)c1C(=O)Nc1cc2nc(-c3ccccc3)cn2c(N2CCOCC2)n1 | null | CCOC(C)=O | CN(C)C=O | CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F | null | train |
US20070072901A1 | COc1ccc(-c2cccc3c(Nc4ccc5ncccc5c4)nccc23)cn1>>O=c1ccc(-c2cccc3c(Nc4ccc5ncccc5c4)nccc23)c[nH]1 | null | Cl | null | null | null | train |
US20090124596A1 | O=C(N[C@@H]1CC[C@H](NC(=O)c2cc(F)cnc2Nc2cccc(Cc3ccccc3)c2)CC1)c1cn2ccccc2n1.O=C(n1ccnc1)n1ccnc1>>O=C(N[C@@H]1CC[C@H](n2c(=O)c3cc(F)cnc3n(-c3cccc(Cc4ccccc4)c3)c2=O)CC1)c1cn2ccccc2n1 | null | CN(C)C=O | null | [H-].[Na+] | null | train |
US20150065531A1 | Cc1ccccc1/C=C/CO>>Cc1ccccc1/C=C/C=O | O=[Mn]=O | null | null | null | null | train |
US20110028515A1 | CC(C)c1ccc(NC(=O)C2(O)CCNCC2)cc1.Fc1ccc(CBr)cc1>>CC(C)c1ccc(NC(=O)C2(O)CCN(Cc3ccc(F)cc3)CC2)cc1 | null | ClCCl | null | CCN(CC)CC | null | train |
US06166006 | O=C(C=Cc1cccc(Br)c1)Nc1ccc(CN2CCCCC2)cc1.[O-]B([O-])Oc1ccc(F)cc1>>O=C(C=Cc1cccc(-c2ccc(F)cc2)c1)Nc1ccc(CN2CCCCC2)cc1 | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | Cc1ccccc1 | null | CCO | O=C([O-])[O-].[K+].[K+] | train |
US20130129753A1 | CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@@H](Cc1ccccc1)c1nccs1)OC)N(C)C(=O)[C@@H](NC(=O)C(C)(C)N(C)C(=O)OC(C)(C)C)C(C)C>>CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@@H](Cc1ccccc1)c1nccs1)OC)N(C)C(=O)[C@@H](NC(=O)C(C)(C)NC)C(C)C | null | ClCCl | null | O=C(O)C(F)(F)F | null | train |
US04954518 | CC(=O)c1cc(Oc2ccccc2)c(NS(C)(=O)=O)cc1O.CCOC=O>>CS(=O)(=O)Nc1cc2occc(=O)c2cc1Oc1ccccc1 | null | Cc1ccccc1 | null | [H-].[Na+] | null | train |
US20060276508A1 | CCOc1cc(CO)ccc1-c1ccc(C(F)(F)F)cc1>>CCOc1cc(C=O)ccc1-c1ccc(C(F)(F)F)cc1 | O=[Mn]=O | ClCCl | null | null | null | train |
US20040019098A1 | Nc1ccc2c(c1)COC2=O.O=C(CCl)OC(=O)CCl>>O=C(CCl)Nc1ccc2c(c1)COC2=O | null | C1CCOC1 | null | O | null | train |
US20010049374A1 | C[Si](C)(C)CCOCCl.Ic1cn[nH]c1>>C[Si](C)(C)CCOCn1cc(I)cn1 | null | C1CCOC1 | null | O | [H-].[Na+] | train |
US04560701 | O=C(O)c1ccsc1COc1ccc(CCCCO)cc1.O=C(OC(=O)C(F)(F)F)C(F)(F)F>>O=C1c2cc(CCCCOC(=O)C(F)(F)F)ccc2OCc2sccc21 | null | ClCCl | null | O | null | train |
US20100168082A1 | CC(C)(C)OC(=O)N1Cc2ncnc(Oc3ccc4[nH]ccc4c3)c2C1.COc1cc(N)cc(C(F)(F)F)c1.O=C(n1ccnc1)n1ccnc1>>COc1cc(NC(=O)n2ccc3cc(Oc4ncnc5c4CNC5)ccc32)cc(C(F)(F)F)c1 | CN(C)c1ccncc1 | CCOC(C)=O | CN(C)C=O | Cl | O=C(O)C(F)(F)F | train |
US20090093485A1 | Cc1ccc(S(=O)(=O)O)c(C)c1.Clc1nc(Cl)nc(Cl)n1>>Cc1ccc(S(=O)(=O)Cl)c(C)c1 | null | CC(C)=O | null | CCN(C(C)C)C(C)C | null | train |
US04910318 | CC(C)(C)OC(=O)ON=C(C#N)c1ccccc1.CNCC1CCSc2c1[nH]c1ccccc21>>CN(CC1CCSc2c1[nH]c1ccccc21)C(=O)OC(C)(C)C | null | C1CCOC1 | null | CCN(CC)CC | null | train |
US20110152273A1 | CCn1cc(B2OC(C)(C)C(C)(C)O2)cn1.COC(=O)c1c(C#N)ccnc1Cl>>CCn1cc(-c2nccc(C#N)c2C(=O)OC)cn1 | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | CCOC(C)=O | COCCOC | O | O=C([O-])[O-].[Na+].[Na+] | train |
US20120010281A1 | BrC(Br)(Br)Br.C=C(CO)[C@H](CC12CCCC(C#N)C1C1(CC2)OCCO1)O[Si](C)(C)C(C)(C)C>>C=C(CBr)[C@H](C[C@@]12CCC[C@@H](C#N)[C@@H]1C1(CC2)OCCO1)O[Si](C)(C)C(C)(C)C | null | ClCCl | null | CCN(CC)CC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | train |
US20120136008A1 | CC1(c2ccncc2)CO1.Cc1ccc2[nH]c3c(c2c1)CN(C)C(C)C3>>Cc1ccc2c(c1)c1c(n2CC(C)(O)c2ccncc2)CC(C)N(C)C1 | null | CN(C)C=O | null | [H-].[Na+] | null | train |
US20100216814A1 | CC(=CBr)c1cccc(F)c1.CN1CCc2[nH]c3ccc(Cl)cc3c2C1>>C/C(=C\n1c2c(c3cc(Cl)ccc31)CN(C)CC2)c1cccc(F)c1 | [Cu]I | CN(C)C=O | null | O=C(O)[C@@H]1CCCN1 | O=P([O-])([O-])[O-].[K+].[K+].[K+] | train |
US20060247210A1 | NC(=S)Nc1cccc(C(=O)O)c1>>Nc1nc2cccc(C(=O)O)c2s1 | null | ClC(Cl)Cl | null | BrBr | null | train |
US20020026060A1 | CC(C)=CC(=O)Cl.CCCCCC(C(=O)OCC)c1ccc(N)cc1>>CCCCCC(C(=O)OCC)c1ccc(NC(=O)C=C(C)C)cc1 | null | ClC(Cl)Cl | null | O | null | train |
US04954518 | CS(=O)(=O)Nc1cc2oc(C(=O)O)cc(=O)c2cc1Oc1ccccc1.O=S(Cl)Cl>>CS(=O)(=O)Nc1cc2oc(C(=O)Cl)cc(=O)c2cc1Oc1ccccc1 | null | ClCCl | null | CN(C)C=O | null | train |
US20090176760A1 | CCc1nc2c(C)cc(C)nc2n1Cc1ccc2c(c1)CCc1ccccc1N2C(C)C#N.C[Si](C)(C)N=[N+]=[N-]>>CCc1nc2c(C)cc(C)nc2n1Cc1ccc2c(c1)CCc1ccccc1N2C(C)c1nnn[nH]1 | null | Cc1ccccc1 | null | CCCC[Sn](=O)CCCC | null | train |
US04992474 | BrCCCCCCBr.Cc1cccc(C)c1CCO>>Cc1cccc(C)c1CCOCCCCCCBr | null | C1CCOC1 | null | O | [H-].[Na+] | train |
US20150011548A1 | CCN1CCN(CC(=O)OC)CC1>>CCN1CCN(CC(=O)O)CC1 | null | Cl | null | null | null | train |
US20060160877A1 | O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F.Oc1ccccc1N1CCOCC1>>O=S(=O)(Oc1ccccc1N1CCOCC1)C(F)(F)F | null | ClCCl | null | CCN(CC)CC | null | train |
US05939443 | CC(C)(Cc1ccc(O)cc1)[N+](=O)[O-].CCO>>CC(=O)O.CC(C)(N)Cc1ccc(O)cc1 | [Pd] | CO | null | null | null | train |
US20100144707A1 | C1COCCN1.CC(C)(C)OC(=O)n1ncc2cc(Nc3nc(-c4cccc(NC(=O)CCl)c4)nc4ccccc34)ccc21>>CC(C)(C)OC(=O)n1ncc2cc(Nc3nc(-c4cccc(NC(=O)CN5CCOCC5)c4)nc4ccccc34)ccc21 | null | CN(C)C=O | null | C1CCOC1 | null | train |
US20110015196A1 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCOC(=O)C1CCNCC1>>CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CC1 | null | O | null | null | null | train |
US20080132539A1 | CC(C)(C)C=O.Cc1cc(N)c(NC(=O)CC[C@H](NC(=O)OC(C)(C)C)C(=O)OCc2ccccc2)cc1C>>Cc1cc(NCC(C)(C)C)c(NC(=O)CC[C@H](NC(=O)OC(C)(C)C)C(=O)OCc2ccccc2)cc1C | null | CC#N | null | CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+] | null | train |
US20160243463A1 | C=C(C)CCl.C=CCC(C(=O)OCC)C(=O)OCC>>C=CCC(CC(=C)C)(C(=O)OCC)C(=O)OCC | null | C1CCOC1 | null | [H-].[Na+] | null | train |
US20030216398A1 | COc1ccc(C(=O)Cl)cc1OC.c1ccc2c(c1)NCCN2>>COc1ccc(C(=O)N2CCNc3ccccc32)cc1OC | null | c1ccncc1 | null | null | null | train |
US20100010035A1 | CCOCCl.CN(C)C=O.Cc1onc(NS(=O)(=O)c2sccc2Br)c1C>>COCCOCN(c1noc(C)c1C)S(=O)(=O)c1sccc1Br | null | CCOC(C)=O | null | [H-].[Na+] | null | train |
US04898854 | COC(=O)[C@H]1C[C@@H](CP(=O)(OC)OC)CCN1C(=O)OCc1ccccc1>>COC(=O)[C@H]1C[C@@H](CP(=O)(O)O)CCN1C(=O)OCc1ccccc1 | null | ClCCl | null | C[Si](C)(C)I | null | train |
US20090286827A1 | Clc1cc(Br)cnc1Cl.Nc1ccc(Cl)cc1>>Clc1ccc(Nc2ncc(Br)cc2Cl)cc1 | null | C1CCOC1 | null | [H-].[Na+] | null | train |
US20080261943A1 | CC(=O)NCCNc1nc(-c2ccccc2)nc2[nH]c(C(=O)N3CCC4(CC3)OCCO4)cc12>>CC(=O)NCCNc1nc(-c2ccccc2)nc2[nH]c(C(=O)N3CCC(=O)CC3)cc12 | null | Cl | null | O=C([O-])O.[Na+] | null | train |
US20100292236A1 | CC(C)CC(CN)c1cccnc1.O=C(O)c1cn(-c2ncccn2)nc1Cl>>CC(C)CC(CNC(=O)c1cn(-c2ncccn2)nc1Cl)c1cccnc1 | null | CN(C)C=O | O | CCN(C(C)C)C(C)C | CN(C)[P+](On1nnc2ccccc21)(N(C)C)N(C)C.F[P-](F)(F)(F)(F)F | train |
US20040162303A1 | N.O=C(c1cnc(Cl)nc1Cl)c1cc(F)cc2ccoc12>>Nc1nc(Cl)ncc1C(=O)c1cc(F)cc2ccoc12 | null | Cc1ccccc1 | null | null | null | train |
US20060063787A1 | BrCCc1ccccc1.CC(C)(C)C(=O)OCn1c(=O)[nH]c(=O)c2c1ncn2Cc1ccccc1>>CC(C)(C)C(=O)OCn1c(=O)n(CCc2ccccc2)c(=O)c2c1ncn2Cc1ccccc1 | null | CN(C)C=O | null | O=C([O-])[O-].[K+].[K+] | null | train |
US05736548 | CCOC(=O)COc1cccc(-c2nc3n(C4CCCC4)[nH]c(CC)c-3c(=O)n2)c1>>CCc1[nH]n(C2CCCC2)c2nc(-c3cccc(OCC(=O)O)c3)nc(=O)c1-2 | null | CCO | null | O | [K+].[OH-] | train |
US20160039794A1 | CN1CCN(C(=O)c2ccc([N+](=O)[O-])c([N+](=O)[O-])c2)CC1>>CN1CCN(C(=O)c2ccc(N)c(N)c2)CC1 | [Pd] | CCOC(C)=O | null | CCO | null | train |
US20140018401A1 | CCCC(=O)c1ccc(NC(C)=O)cc1.CCI>>CCC(CC)C(=O)c1ccc(NC(C)=O)cc1 | null | C1CCOC1 | null | CC(C)[N-]C(C)C.[Li+] | null | train |
US04859684 | CO.On1c(-c2ccccc2)nc2ccc(Cn3ccnc3)cc21>>COn1c(-c2ccccc2)nc2ccc(Cn3ccnc3)cc21 | null | CO | null | [Na] | C[O-].[Na+] | train |
US20090264431A1 | CC(C)(C)OC(=O)N1C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H]1COc1ccccc1>>CC(C)(C)OC(=O)N1C[C@@H](O)C[C@@H]1COc1ccccc1 | null | C1CCOC1 | null | CCCC[N+](CCCC)(CCCC)CCCC.[F-] | null | train |
US20120115845A1 | CN(C)[C@H]1CCNC1.NC(=O)c1cc(F)ccc1Cl>>CN(C)[C@H]1CCN(c2ccc(Cl)c(C(N)=O)c2)C1 | null | CS(C)=O | null | O | O=C([O-])[O-].[K+].[K+] | train |
US20120088755A1 | COc1ccc2c(c1)CCN(C1CCNCC1)C(=O)N2.Cc1cc(Oc2cc(Cl)ncn2)ccc1[N+](=O)[O-]>>COc1ccc2c(c1)CCN(C1CCN(c3cc(Oc4ccc([N+](=O)[O-])c(C)c4)ncn3)CC1)C(=O)N2 | null | CN(C)C=O | null | CCN(C(C)C)C(C)C | O | train |
US20160052888A1 | O=C1N[C@@]2(CC[C@H](c3ccc4c(c3)CC[C@@H](CO)C4)C2)CO1>>O=C[C@@H]1CCc2cc([C@H]3CC[C@]4(COC(=O)N4)C3)ccc2C1 | null | ClCCl | null | CS(C)=O | O=C(Cl)C(=O)Cl | train |
US05246965 | ClCCCCCBr.N#Cc1ccc(O)cc1>>N#Cc1ccc(OCCCCCCl)cc1 | null | CN(C)C=O | null | [H][H] | [H-].[Na+] | train |
US05534481 | Cn1nc2cccc(OCC3CC3)c2c1S(N)(=O)=O>>Cn1nc2cccc(O)c2c1S(N)(=O)=O | null | CC(=O)O | null | Cl | null | train |
US20070179165A1 | CCC(O)c1ccccc1.Cc1cc(C)c(-n2ccc3c(Cl)nn(C)c(=O)c32)c(C)c1>>CCC(Oc1nn(C)c(=O)c2c1ccn2-c1c(C)cc(C)cc1C)c1ccccc1 | null | CN(C)C=O | O | [H-].[Na+] | null | train |
US06130241 | CCCCC(I)CCCCl.O=C1NC(=O)C2CC12>>O=C1C2CC2C(=O)N1CCCCCl | null | CN(C)C=O | null | O | [H-].[Na+] | train |
US20090149439A1 | Cc1cc(C(=O)NCCO)ncc1C(c1cc(F)ccc1F)S(=O)(=O)c1ccc(F)cc1.O=S(Cl)Cl>>Cc1cc(C(=O)NCCCl)ncc1C(c1cc(F)ccc1F)S(=O)(=O)c1ccc(F)cc1 | null | O=S(Cl)Cl | null | ClCCl | null | train |
US20060106025A1 | COc1ccc([N+](=O)[O-])c2c1sc1ccccc12>>O=[N+]([O-])c1ccc(O)c2sc3ccccc3c12 | null | O | null | Cl | c1ccncc1 | train |
US20150284327A1 | COC(=O)CCl.COC(=O)c1cccc([N+](=O)[O-])c1>>COC(=O)Cc1ccc(C(=O)OC)cc1[N+](=O)[O-] | null | CN(C)C=O | null | Cl | CC(C)(C)[O-].[K+] | train |
US20070088001A1 | CC(=O)COCc1ccccc1.N.[C-]#N>>CC(N)(C#N)COCc1ccccc1 | null | CO | ClCCl | [Cl-].[NH4+] | null | train |
US20030013743A1 | O=C(Cl)C(=O)Cl.O=C(O)c1cccnc1Oc1cccnc1>>O=C(Cl)c1cccnc1Oc1cccnc1 | null | C1CCOC1 | null | null | null | train |
US20100197908A1 | C1CCNC1.CC(Oc1ccc(CCc2ccc(CCl)cc2)nn1)c1ccccc1>>CC(Oc1ccc(CCc2ccc(CN3CCCC3)cc2)nn1)c1ccccc1 | null | C1CCOC1 | O | null | null | train |
US20070043064A1 | C#CCN(c1cccc(C(=O)C=CN(C)C)c1)S(=O)(=O)C(C)C.Nc1[nH]ncc1[N+](=O)[O-]>>C#CCN(c1cccc(-c2ccnc3c([N+](=O)[O-])cnn23)c1)S(=O)(=O)C(C)C | null | CC(=O)O | null | CCOC(C)=O | null | train |
US20090076068A1 | CCCCCCN=C=O.Cc1ccnc2[nH]c(=O)n(C(=O)OC(C)(C)C)c12>>CCCCCCNC(=O)n1c(=O)[nH]c2c(C)ccnc21 | CN(C)c1ccncc1 | Cc1ccccc1 | null | null | null | train |
US20040254158A1 | CCOC(C)=O.COc1ccc(-n2nc(C(F)(F)F)c3c2C(=O)NCC3)cc1.N#N.c1cnc2c(c1)ccc1cccnc12>>COc1ccc(-n2nc(C(F)(F)F)c3c2C(=O)N(c2ccc(C4(C5=NCCO5)CC4)cc2)CC3)cc1 | I[Cu]I | CS(C)=O | null | O=C([O-])[O-].[K+].[K+] | null | train |
US20060025467A1 | COC(=O)/C=C/c1ccccc1.c1ccc2[nH]ccc2c1>>COC(=O)CC(c1ccccc1)n1ccc2ccccc21 | null | CN(C)C=O | null | O | [H-].[Na+] | train |
US04695398 | C1CCOC1.CCCCCC1CCC(=O)CC1.Fc1ccc(Br)cc1F>>CCCCCC1(F)CCC(O)CC1F.c1ccccc1 | null | C1CCOC1 | null | Cl | O | train |
US20090270436A1 | CC(C)(C)OC(=O)N1CCC2(CC1)CC(=O)c1cc(N)ccc1O2.COC(=O)Cl>>COC(=O)Nc1ccc2c(c1)C(=O)CC1(CCN(C(=O)OC(C)(C)C)CC1)O2 | null | c1ccncc1 | null | null | null | train |
US20110245241A1 | CC1(C)OCCn2c1nc(-c1nnc(Cc3ccc(F)cc3)o1)c(OCc1ccccc1)c2=O>>CC1(C)OCCn2c1nc(-c1nnc(Cc3ccc(F)cc3)o1)c(O)c2=O | null | O=C(O)C(F)(F)F | null | null | null | train |
US20140045862A1 | CC(C)(C)OC(=O)N(c1cscn1)S(=O)(=O)c1c(F)cc(O[C@H]2CCCC[C@@H]2c2cn(C3CCCCO3)nc2[N+](=O)[O-])cc1F>>O=[N+]([O-])c1n[nH]cc1[C@H]1CCCC[C@@H]1Oc1cc(F)c(S(=O)(=O)Nc2cscn2)c(F)c1 | null | CO | null | ClCCl | O=C(O)C(F)(F)F | train |
US20080319200A1 | CCOC(=O)[C@H](N)[C@@H](O)c1ccc(S(C)(=O)=O)cc1.O=C(Cl)C(Cl)Cl>>CCOC(=O)[C@H](NC(=O)C(Cl)Cl)[C@@H](O)c1ccc(S(C)(=O)=O)cc1 | null | CO | null | CCN(CC)CC | null | train |
US05026858 | COc1cc(NC(C)=O)c([N+](=O)[O-])cc1C(=O)O.NC1CCN(Cc2ccccc2)CC1.O=C(O)/C=C/C(=O)O>>COc1cc(NC(C)=O)c([N+](=O)[O-])cc1C(=O)NC1CCN(Cc2ccccc2)CC1.O=C(O)/C=C/C(=O)O | null | CO | ClCCl | C(=NC1CCCCC1)=NC1CCCCC1 | null | train |
US20040151687A1 | CCCCCCCCCCN1CCCCC1.ClCCCBr>>CCCCCCCCCC[N+]1(CCCCl)CCCCC1.[Br-] | null | CO | null | null | null | train |
US20130158025A1 | CCOC(=O)CC(=O)c1cccc(C(F)(F)F)c1.Cc1ccc(-c2c(C)n[nH]c2N)cc1>>Cc1ccc(-c2c(C)nn3c(-c4cccc(C(F)(F)F)c4)cc(=O)[nH]c23)cc1 | null | c1ccncc1 | null | null | null | train |
US20120178756A1 | CC(C)S(=O)(=O)c1ccc(-c2cnc(N)c(C#Cc3cccc(OCCCNC(=O)OC(C)(C)C)c3)n2)cc1>>CC(C)S(=O)(=O)c1ccc(-c2cnc(N)c(C#Cc3cccc(OCCCN)c3)n2)cc1 | null | ClCCl | null | O=C(O)C(F)(F)F | null | train |
US20070105943A1 | N#Cc1ccc(OCc2ccccn2)cc1>>NCc1ccc(OCc2ccccn2)cc1 | null | C1CCOC1 | null | [Al+3].[H-].[H-].[H-].[H-].[Li+] | null | train |
Subsets and Splits
No community queries yet
The top public SQL queries from the community will appear here once available.