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 |
|---|---|---|---|---|---|---|---|
US06008230 | O=[N+]([O-])c1cccc2cc(Br)cnc12.OB(O)Oc1ccccc1>>O=[N+]([O-])c1cccc2cc(-c3ccccc3)cnc12 | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | CCOC(C)=O | COCCOC | O=C([O-])[O-].[Na+].[Na+] | null | train |
US20060025601A1 | O=C1NCC2c3ccccc3CC12>>c1ccc2c(c1)CC1CNCC21 | null | C1CCOC1 | null | [Al+3].[H-].[H-].[H-].[H-].[Li+] | null | train |
US20070249670A1 | COC(=O)[C@@H](N)[C@@H](C)OC1CCC1.Nc1cc2ccccc2cc1C(=O)O>>COC(=O)[C@@H](NC(=O)c1cc2ccccc2cc1N)[C@@H](C)OC1CCC1 | 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 |
US20060111375A1 | CC(C)(C)C(=O)Nc1ncccc1C=O>>Nc1ncccc1C=O | null | Cl | null | null | null | train |
US20080090818A1 | CC(C)(C)OC(=O)N(c1ccc(N2CCOCC2)cc1)c1ncc(-c2ccc3c(c2)S(=O)(=O)NC3=O)n2ncnc12>>O=C1NS(=O)(=O)c2cc(-c3cnc(Nc4ccc(N5CCOCC5)cc4)c4ncnn34)ccc21 | null | C1COCCO1 | Cl | null | null | train |
US20090048306A1 | CC(C)OB(OC(C)C)OC(C)C.CCOc1ccc(OC(F)(F)F)c(Br)c1>>CCOc1ccc(OC(F)(F)F)c(B(O)O)c1 | null | C1CCOC1 | null | [Li]CCCC | null | train |
US06562978B1 | CC(=O)N1CCC(C(=O)N(CCCN2CCC(Cc3ccc(N)cc3)CC2)c2ccc(Cl)c(Cl)c2)CC1.CS(=O)(=O)Cl>>CC(=O)N1CCC(C(=O)N(CCCN2CCC(Cc3ccc(NS(C)(=O)=O)cc3)CC2)c2ccc(Cl)c(Cl)c2)CC1 | null | C1CCOC1 | null | CCN(CC)CC | [Na+].[OH-] | train |
US20140121377A1 | CC(=O)c1ccc(Br)nc1.c1c[nH]nn1>>CC(=O)c1ccc(-n2ccnn2)nc1 | null | CN(C)C=O | O | [Cl-].[NH4+] | O=C([O-])[O-].[K+].[K+] | train |
US20050054626A1 | CC(C)(C)N[C@@H]1CC[C@H](NC(=O)CNC(=O)OCc2ccccc2)[C@H](CO)C1>>CC(C)(C)N[C@@H]1CC[C@H](NC(=O)CN)[C@H](CO)C1 | [Pd] | CO | null | null | null | train |
US04948882 | COC(=O)C=Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)nc1N.O=C(OC(=O)c1ccccc1)c1ccccc1>>COC(=O)C=Cc1cn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)nc1NC(=O)c1ccccc1 | null | CCO | null | null | null | train |
US20100125062A1 | Cc1cc(-c2cccnc2F)ccn1.Oc1ccc(Cc2nc3ccccc3[nH]2)cc1>>Cc1cc(-c2cccnc2Oc2ccc(Cc3nc4ccccc4[nH]3)cc2)ccn1 | null | O | null | O=C([O-])[O-].[Cs+].[Cs+] | null | train |
US20090105253A1 | CC(Br)c1ccccc1.CCNC(=O)c1ccc(-n2cc(C(=O)NC3CC3)nn2)c(O)c1>>CCNC(=O)c1ccc(-n2cc(C(=O)NC3CC3)nn2)c(OC(C)c2ccccc2)c1 | null | CN(C)C=O | null | O | O=C([O-])[O-].[K+].[K+] | train |
US20020169171A1 | CCOC(=O)c1ccncc1N.O=C(Cl)Cl.OCc1cc2cc(-c3ccccc3)ccc2o1>>CCOC(=O)c1ccncc1NC(=O)OCc1cc2cc(-c3ccccc3)ccc2o1 | CN(C)c1ccncc1 | Cc1ccccc1 | null | Cl | c1ccncc1 | train |
US20080275035A1 | CC(C)(C)[Si](C)(C)OC[C@H](Cn1cc([N+](=O)[O-])nc1Cl)OC1CCCCO1>>O=[N+]([O-])c1cn2c(n1)OC[C@@H](OC1CCCCO1)C2 | null | C1CCOC1 | null | CCCC[N+](CCCC)(CCCC)CCCC.[F-] | null | train |
US20110003815A1 | C=C(OC)c1ccc([C@]2(c3ccc(OCc4ccccn4)cc3)CC3CCC2C3)cc1.CCOC(=O)C(Cl)=NO>>CCOC(=O)c1cc(-c2ccc([C@]3(c4ccc(OCc5ccccn5)cc4)CC4CCC3C4)cc2)on1 | null | C1CCOC1 | null | CCN(CC)CC | O=C(O)C(F)(F)F | train |
US20110288065A1 | C[C@H](Nc1nc(Nc2cnccn2)cc(N2CC(O)C2)n1)c1ccc(F)cc1>>C[C@H](Nc1nc(Nc2cnccn2)cc(N2CC(=O)C2)n1)c1ccc(F)cc1 | null | CCOC(C)=O | CS(C)=O | CCN(CC)CC | [Cl-].[NH4+] | train |
US05792765 | ClCCCl.Nc1ccc(Br)cn1.O=C(Cl)OCC(Cl)(Cl)Cl>>Cl.O=C=Nc1ccc(Br)cn1 | null | ClCCCl | null | null | null | train |
US20150065522A1 | COc1c(C(C)C)c(C)nc2c(-c3cnn(COCC[Si](C)(C)C)c3)cnn12>>Cc1[nH]c2c(-c3cn[nH]c3)cnn2c(=O)c1C(C)C | null | CO | null | Cl | ClCCl | train |
US20140315881A1 | CCOC(=O)Cc1ccccc1.O=C(Cl)CCCl>>CCOC(=O)Cc1ccc(C(=O)CCCl)cc1 | null | ClCCl | null | [Al+3].[Cl-].[Cl-].[Cl-] | null | train |
US20080207616A1 | Cc1ccc(NC(=O)c2cccc(C(C)(C)C#N)c2)cc1NC(=O)c1ccc2nc(Cl)cnc2c1.NCCCN1CCCCC1>>Cc1ccc(NC(=O)c2cccc(C(C)(C)C#N)c2)cc1NC(=O)c1ccc2nc(NCCCN3CCCCC3)cnc2c1 | null | CO | null | null | null | train |
US20070066819A1 | Cc1ccccc1.O=C(Cl)CCl>>O=C(CCl)C1CCCC1 | null | O | null | O=C([O-])[O-].[K+].[K+] | null | train |
US20070197521A1 | CC1(CO)NC(=O)N(c2ccc(Cl)c(C(F)(F)F)c2)C1=O.CS(=O)(=O)Cl>>CC1(COS(C)(=O)=O)NC(=O)N(c2ccc(Cl)c(C(F)(F)F)c2)C1=O | null | ClCCl | null | null | null | train |
US20140315933A1 | C=CCBr.O=S(=O)(Nc1nccs1)c1cc(F)c(F)cc1F>>C=CCN(c1nccs1)S(=O)(=O)c1cc(F)c(F)cc1F | null | C1CCOC1 | null | O=C([O-])[O-].[K+].[K+] | null | train |
US20060258714A1 | Cc1ccc(S(=O)(=O)OC[C@H]2C=Cc3ccc(F)c(-c4ccccc4Cl)c3O2)cc1>>Cc1ccc(S(=O)(=O)OC[C@H]2CCc3ccc(F)c(-c4ccccc4Cl)c3O2)cc1 | O=[Pt]=O | CCO | CCOC(C)=O | null | null | train |
US20120108582A1 | C[C@H](c1ccccc1)N1C[C@@H]2CC=CC[C@@]2(NC(=O)OC(C)(C)C)C1.O=C(Cl)OCc1ccccc1>>CC(C)(C)OC(=O)N[C@@]12CC=CC[C@H]1CN(C(=O)OCc1ccccc1)C2 | null | ClCCl | null | null | null | train |
US06235731B1 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CCOC(=O)CCc1ccc(N)cc1>>CCOC(=O)CCc1ccc(NC(=O)OC(C)(C)C)cc1 | null | O | null | C1CCOC1 | CCN(CC)CC | train |
US20130217893A1 | CCOC(=O)CN(CCC(=O)NC1CC1)C(=O)OCc1ccccc1>>O=C1CN(C(=O)OCc2ccccc2)CC1C(=O)NC1CC1 | null | Cc1ccccc1 | null | CC(C)(C)[O-].[K+] | null | train |
US20150329489A1 | CCO.N#C[C@@H]1C[C@@H]2C[C@@H]2N1C(=O)[C@@H](N)C12CC3CC(CC(O)(C3)C1)C2.O=C=O>>N#C[C@@H]1C[C@@H]2C[C@@H]2N1C(=O)[C@@H](N)C12CC3CC(CC(O)(C3)C1)C2.O=C([O-])O | null | CCO | null | null | null | train |
US20100184808A1 | CC1C[C@H]2CN(C(=O)OC(C)(C)C)[C@H](CNC(=O)C(F)(F)F)[C@H]2C1>>CC1C[C@H]2CN[C@H](CNC(=O)C(F)(F)F)[C@H]2C1 | null | ClCCl | null | O=C(O)C(F)(F)F | null | train |
US20060040954A1 | COC(=O)C(CCBr)NC(=O)OC(C)(C)C.O=C(NCCCCc1ccc(O)cc1)OCc1ccccc1>>COC(=O)C(CCOc1ccc(CCCCNC(=O)OCc2ccccc2)cc1)NC(=O)OC(C)(C)C | null | CCOC(C)=O | CN(C)C=O | O=C([O-])[O-].[K+].[K+] | null | train |
US20040106645A1 | COc1ccc2oc(=O)cc(O)c2c1>>O=c1cc(O)c2cc(O)ccc2o1 | null | ClCCl | null | BrB(Br)Br | null | train |
US20070179151A1 | COc1cc(C=CC(=O)O)cc(OC)c1>>COc1cc(CCC(=O)O)cc(OC)c1 | [Pd] | CCOC(C)=O | CO | [H][H] | null | train |
US20080051399A1 | C[C@@H]1CC(=O)c2ncnc(N3CCN(C(=O)OC(C)(C)C)CC3)c21.[Li]C>>C[C@@H]1CC(C)(O)c2ncnc(N3CCN(C(=O)OC(C)(C)C)CC3)c21 | null | C1CCOC1 | null | CCOCC | null | train |
US20160083391A1 | COC(=O)c1cnc(C(C)C)n1N>>CC(C)c1ncc(C(=O)O)n1N | null | C1CCOC1 | O | [Na+].[OH-] | null | train |
US05502065 | O=C(OCc1ccccc1)N1CCC[C@@H]1Cc1c[nH]c2ccc(-c3ccc(CO)cc3)cc12>>OCc1ccc(-c2ccc3[nH]cc(C[C@H]4CCCN4)c3c2)cc1 | null | CCO | null | CC(=O)Cl | null | train |
US20040220234A1 | II.OCCC(O)C(F)(F)F>>OC(CCI)C(F)(F)F | null | ClCCl | null | c1c[nH]cn1 | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | train |
US20140171390A1 | CC(C)(C)[Si](C)(C)OCCN[C@@H]1CC[C@@H](CC(=O)N[C@H]2Cc3cccc(C(=O)O)c3OB2O)CC1>>O=C(C[C@@H]1CC[C@@H](NCCO)CC1)N[C@H]1Cc2cccc(C(=O)O)c2OB1O | null | C1COCCO1 | null | Cl | null | train |
US20090062253A1 | CC(C)(C)c1ccc(C2=NCCCn3cncc32)cc1>>CC(C)(C)c1ccc(C2NCCCn3cncc32)cc1 | null | CO | null | O | [BH4-].[Na+] | train |
US04001223 | C1CNCCN1.ClCC=Cc1ccccc1>>C(=Cc1ccccc1)CN1CCNCC1 | null | CC(C)O | null | null | null | train |
US20130143863A1 | BrP(Br)Br.CC(O)c1cncc(N2CCc3cc(Cl)ccc3C2=O)c1>>CC(Br)c1cncc(N2CCc3cc(Cl)ccc3C2=O)c1 | null | ClCCl | null | null | null | train |
US20030199503A1 | CN(C(=O)c1ccc(Cl)cc1Cl)c1nc(-c2ccccc2)sc1C(=O)OC(C)(C)C>>CN(C(=O)c1ccc(Cl)cc1Cl)c1nc(-c2ccccc2)sc1C(=O)O | null | ClCCl | O=C(O)C(F)(F)F | null | null | train |
US20150225449A1 | C[C@H]1[C@H](NC(=O)OC(C)(C)C)C(=O)N(C(=O)C2CCOCC2)c2ccc(C#N)cc2N1C(=O)C1CCOCC1>>C[C@H]1[C@H](NC(=O)OC(C)(C)C)C(=O)Nc2ccc(C#N)cc2N1C(=O)C1CCOCC1 | null | CCOC(C)=O | CO | [Na+].[OH-] | null | train |
US20070197577A1 | COC(=O)c1ccc(CBr)cc1.Nc1cccc(S)c1>>COC(=O)c1ccc(CSc2cccc(N)c2)cc1 | null | CO | null | [Na+].[OH-] | null | train |
US20050153959A1 | CCc1cc(CC(N)C(=O)OC)cc2c(C)n[nH]c12.O=C(c1ncc[nH]1)c1ncc[nH]1.O=C1Nc2ccccc2CN1C1CCNCC1>>CCc1cc(CC(NC(=O)N2CCC(N3Cc4ccccc4NC3=O)CC2)C(=O)OC)cc2c(C)n[nH]c12 | null | C1CCOC1 | null | null | null | train |
US04011230 | CNC.O=[N+]([O-])C=Cc1ccccc1.S=C=S>>CN(C)C(=S)SC(C[N+](=O)[O-])c1ccccc1 | null | CO | null | null | null | train |
US20090269305A1 | CC(C)(C)N.CCOC(=O)CS(=O)(=O)Cl>>CCOC(=O)CS(=O)(=O)NC(C)(C)C | null | C1CCOC1 | null | null | null | train |
US20080242694A1 | CC(C)(C)OC(=O)NCCN.CC(C)(C)OC(=O)NCCNC(=O)CCCCc1ccccc1.O=C(O)CCCCc1ccccc1.Oc1cccc2[nH]nnc12>>NCCn1c(CCCCc2ccccc2)nnc1-c1ccc2cnccc2c1 | null | CN(C)C=O | null | CCN=C=NCCCN(C)C | null | train |
US20150087639A1 | O=[N+]([O-])c1ccc(F)c(F)c1.c1cn[nH]c1>>O=[N+]([O-])c1ccc(-n2cccn2)c(F)c1 | null | CS(C)=O | O | O=C([O-])[O-].[K+].[K+] | null | train |
US04766133 | CC(C)(C)[Mg]Cl.CCOC(=O)Cl.Cc1cccnc1C>>CCOC(=O)N1C=CC(C(C)(C)C)C(C)=C1C | [Cu]I | C1CCOC1 | null | null | null | train |
US20020016328A1 | CC(C)=O.CCC(CC)Nc1cc(C)nc(Oc2c(C)cc(Br)cc2C)c1C>>CCC(CC)Nc1cc(C)nc(Oc2c(C)cc(C(C)(C)O)cc2C)c1C | null | C1CCOC1 | null | [Li]CCCC | null | train |
US20110190334A1 | Cc1c(Nc2ccc(I)cc2F)c(N)c2n(c1=O)CCO2.O=S(=O)(Cl)C1CC(OCc2ccccc2)C1>>Cc1c(Nc2ccc(I)cc2F)c(NS(=O)(=O)C2CC(OCc3ccccc3)C2)c2n(c1=O)CCO2 | null | c1ccncc1 | null | null | null | train |
US20130210625A1 | Cc1ccc(C#C[Si](C)(C)C)c(CC(=O)O)c1>>C#Cc1ccc(C)cc1CC(=O)O | null | CO | null | O=C([O-])[O-].[K+].[K+] | null | train |
US04112095 | Clc1ccc(-c2ccc(Cl)nn2)cc1.NNC=O>>Clc1ccc(-c2ccc3nncn3n2)cc1 | null | CCCCO | null | null | null | train |
US20070197558A1 | Nc1ccc(Br)cc1.O=[N+]([O-])c1cc(S(=O)(=O)Cl)ccc1Cl>>O=[N+]([O-])c1cc(S(=O)(=O)Nc2ccc(Br)cc2)ccc1Cl | null | CC(=O)O | null | CC(=O)[O-].[Na+] | null | train |
US20100016261A1 | BrBr.COc1cc(C=O)cc(OC)c1OC>>COc1cc(C=O)c(Br)c(OC)c1OC | null | ClC(Cl)Cl | O | null | null | train |
US20130303551A1 | Cn1ncc(C(=O)NC[C@@H]2CCN(C(=O)C3CC3)C2)c1NC(=O)c1ccc(Br)cc1F>>Cn1ncc2c(=O)n(C[C@@H]3CCN(C(=O)C4CC4)C3)c(-c3ccc(Br)cc3F)nc21 | Cl[Ti](Cl)(Cl)Cl | ClCCCl | ClCCl | null | null | train |
US20150218124A1 | C=Cc1c(C#N)cc(O)c(O)c1C#N>>CCc1c(C#N)cc(O)c(O)c1C#N | [Pd] | CO | null | null | null | train |
US20040087789A1 | CC(=O)N1CCNCC1.CC(C)N(C=Nc1ncc(C#Cc2ccc(Cl)cc2)c(Cl)n1)C(C)C>>CC(=O)N1CCN(c2nc(N=CN(C(C)C)C(C)C)ncc2C#Cc2ccc(Cl)cc2)CC1 | null | CC#N | null | null | null | train |
US20140243288A1 | CC1(C)OB(c2ccc(N3C[C@H](CO)OC3=O)cc2F)OC1(C)C.Cn1nnc(N2Cc3ccc(Br)cc3C2)n1>>Cn1nnc(N2Cc3ccc(-c4ccc(N5C[C@H](CO)OC5=O)cc4F)cc3C2)n1 | null | C1COCCO1 | O | O=C([O-])[O-].[Cs+].[Cs+] | null | train |
US20160207883A1 | COc1cc(F)c([N+](=O)[O-])cc1F.Nc1ccc(N2CC(OCCOC3CCCCO3)C2)cc1>>COc1cc(Nc2ccc(N3CC(OCCOC4CCCCO4)C3)cc2)c([N+](=O)[O-])cc1F | null | CN(C)C=O | null | CCN(C(C)C)C(C)C | O | train |
US04186199 | C1=Nc2ccccc2N2CCc3cccc1c32.C[Mg]Br>>CC1Nc2ccccc2N2CCc3cccc1c32 | null | C1CCOC1 | CCOCC | [NH4+].[OH-] | null | train |
US20030236412A1 | CCOC(=O)C(C(C)=O)C(C)=O.NNc1cccc(F)c1>>CCOC(=O)c1c(C)nn(-c2cccc(F)c2)c1C | null | CCO | null | Cl | c1ccncc1 | train |
US20060030612A1 | FC(F)(F)c1cccc2c(-c3ccccc3)n[nH]c12.OB(O)c1ccccc1>>FC(F)(F)c1cccc2c(-c3ccccc3)n(-c3ccccc3)nc12 | null | ClCCl | null | c1ccncc1 | null | train |
US20150038498A1 | CN1CCN(C(=O)[C@H](O)C(C)(C)C)[C@H](C(=O)NCc2cc(Cl)ccc2CNC(=O)OC(C)(C)C)C1.O=C(O)C(F)(F)F>>CN1CCN(C(=O)[C@H](O)C(C)(C)C)[C@H](C(=O)NCc2cc(Cl)ccc2CN)C1.O=C(O)C(F)(F)F | null | ClCCl | null | null | null | train |
US06248739B1 | CON(C)C(C)=O.Fc1ccc(CN2CCOCC2)cc1Br>>CC(=O)c1cc(CN2CCOCC2)ccc1F | null | C1CCOC1 | null | [Li]CCCC | null | train |
US05229400 | OCC#Cc1ccncc1>>OCCCC1CCNCC1 | [Rh] | null | null | null | null | train |
US20120129832A1 | CCOC(=O)C(Br)CC.N#Cc1ccc(O)cc1>>CCOC(=O)C(CC)Oc1ccc(C#N)cc1 | null | O | null | CC#N | O=C([O-])[O-].[K+].[K+] | train |
US04029815 | BrBr.Cc1c(Nc2ccccc2C(=O)O)cccc1C(F)(F)F>>Cc1c(Nc2ccc(Br)cc2C(=O)O)cccc1C(F)(F)F | null | CC(=O)O | null | null | null | train |
US20030144283A1 | COC(=O)c1ccc(CBr)cc1.c1ccc2[nH]c(N3CCCC3)nc2c1>>COC(=O)c1ccc(Cn2c(N3CCCC3)nc3ccccc32)cc1 | null | CN(C)C=O | null | O | [H-].[Na+] | train |
US20040121964A1 | C#C[C@H]1CC[C@@H](C#N)N1C(=O)CCl.NC1(CO)CCCC1>>C#C[C@H]1CC[C@@H](C#N)N1C(=O)CNC1(CO)CCCC1 | null | CC#N | null | null | null | train |
US20160115179A1 | C1COCCOCCOCCOCCOCCO1.CN1C(=O)C(=O)c2cc(F)ccc21.C[Si](C)(C)c1ccccc1OS(=O)(=O)C(F)(F)F.c1ccncc1>>CN1C(=O)C(Oc2ccccc2)(c2ccccn2)c2cc(F)ccc21 | null | C1CCOC1 | null | [F-].[K+] | null | train |
US20070161681A1 | COC(=O)[C@@H](C)CO.N#Cc1ccc(O)cc1F>>COC(=O)[C@@H](C)COc1ccc(C#N)c(F)c1 | null | CCOC(C)=O | null | CCOC(=O)N=NC(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | train |
US20060100229A1 | CCOC(=O)c1cc(CC(C)(C)NC(=O)OC(C)(C)C)n(CCOC)n1>>COCCn1nc(C(=O)O)cc1CC(C)(C)NC(=O)OC(C)(C)C | null | CO | O | [Li+].[OH-] | null | train |
US20080009435A1 | C=C(C)C(=O)N1CCC[C@]12CCN([C@H](CC(C)C)C(=O)OCc1ccccc1)C2=O>>C=C(C)C(=O)N1CCC[C@]12CCN([C@H](CC(C)C)C(=O)O)C2=O | null | CO | null | O | [Na+].[OH-] | train |
US20080058328A1 | CC(=O)Nc1ccccc1C(=O)CNCCc1ccc(Cl)cc1Br>>CC(=O)Nc1ccccc1C(O)CNCCc1ccc(Cl)cc1Br | null | CO | null | [BH4-].[Na+] | null | train |
US20020156295A1 | Brc1ccccc1-c1ccccc1.CC(C)(C)P(Cl)C(C)(C)C>>CC(C)(C)P(c1ccccc1-c1ccccc1)C(C)(C)C | null | C1CCOC1 | null | II | [Mg] | train |
US20110034515A1 | NCc1ccc2[nH]c(C(F)(F)F)cc2c1.O=C(O)c1ccc(C(F)(F)F)nc1>>O=C(NCc1ccc2[nH]c(C(F)(F)F)cc2c1)c1ccc(C(F)(F)F)cn1 | CN(C)C=O | ClCCl | null | CCN(CC)CC | O=C(Cl)C(=O)Cl | train |
US20090143461A1 | COC(=O)c1ccc(CCC[C@H]2[C@H](Cl)C[C@@H](OC3CCCCO3)[C@@H]2C=O)s1.COP(=O)(CC(=O)CCC[C@H](C)O[Si](C)(C)C(C)(C)C)OC>>COC(=O)c1ccc(CCC[C@H]2[C@H](Cl)C[C@@H](OC3CCCCO3)[C@@H]2/C=C/C(=O)CCC[C@H](C)O[Si](C)(C)C(C)(C)C)s1 | null | C1CCOC1 | null | [H-].[Na+] | null | train |
US20140371269A1 | CC(C)(C)OC(=O)N1CC[C@@H](O)[C@H](c2ccccc2)C1.CI>>CO[C@@H]1CCN(C(=O)OC(C)(C)C)C[C@H]1c1ccccc1 | null | CN(C)C=O | null | O | [H-].[Na+] | train |
US20160244437A1 | COCCOCCOCCNC(=O)c1cccc(-c2cc(C[C@H](NC(=O)[C@@H]3CC[C@@H](CNC(=O)OC(C)(C)C)CC3)C(=O)Nc3ccc(-c4nnn[nH]4)cc3)ccc2C)c1.Cl>>COCCOCCOCCNC(=O)c1cccc(-c2cc(C[C@H](NC(=O)[C@@H]3CC[C@@H](CN)CC3)C(=O)Nc3ccc(-c4nnn[nH]4)cc3)ccc2C)c1.Cl | null | C1COCCO1 | null | CC#N | null | train |
US05130335 | CCO.Cc1cc(C(=O)O)cc(C)c1O>>CCOC(=O)c1cc(C)c(O)c(C)c1 | null | O | null | Cl | null | train |
US20130237555A1 | CO.O=C(O)c1cnccc1Cl>>COC(=O)c1cnccc1Cl | null | ClCCl | null | CN(C)C=O | O=C(Cl)C(=O)Cl | train |
US20050014952A1 | COC(=O)C1CSC(c2ccc(F)cc2)=N1>>O=C(O)C1CSC(c2ccc(F)cc2)=N1 | null | C1CCOC1 | O | [K+].[OH-] | null | train |
US20140024650A1 | O=C(c1ccc(OCc2ccccc2)cc1)N1CCCCC1>>O=C(c1ccc(O)cc1)N1CCCCC1 | [Pd] | CCO | null | null | null | train |
US20040157890A1 | CCOC(=O)CBr.CCc1ccccc1O>>CCOC(=O)COc1ccccc1CC | null | CC#N | CCOC(C)=O | O=C([O-])[O-].[Cs+].[Cs+] | null | train |
US20100113462A1 | CCOC(=O)C1(NC(=O)c2cccc(C)c2C=C(C)C)Cc2ccc(F)cc2C1>>CC(C)=Cc1c(C)cccc1C(=O)NC1(C(=O)O)Cc2ccc(F)cc2C1 | null | CCO | null | O | [K+].[OH-] | train |
US20160009701A1 | CCOC(=O)c1ccc2[nH]c3c(C(N)=O)cc(Br)cc3c2c1>>NC(=O)c1cc(Br)cc2c1[nH]c1ccc(C(=O)O)cc12 | null | C1CCOC1 | CO | [Na+].[OH-] | null | train |
US03987160 | NC(=O)c1nn[nH]c1N.O=C(Cl)c1ccccc1>>NC(=O)c1nn[nH]c1NC(=O)c1ccccc1 | null | [Na+] | [OH-] | null | null | train |
US20160145247A1 | CC(C)(C)OC(=O)Cc1ccccc1OCc1ccc(C#N)c(-c2cccc(CNC(=O)OC(C)(C)C)c2)c1>>N#Cc1ccc(COc2ccccc2CC(=O)O)cc1-c1cccc(CN)c1 | null | C1COCCO1 | null | Cl | null | train |
US20140288040A1 | CC(C)(C)S(=O)NC(CC(=O)O)c1ccc(F)c(Oc2ccccc2)c1F.Nc1ccncc1>>CC(C)(C)S(=O)NC(CC(=O)Nc1ccncc1)c1ccc(F)c(Oc2ccccc2)c1F | null | CN(C)C=O | null | CCN=C=NCCCN(C)C | On1nnc2ccccc21 | train |
US20080312226A1 | Cc1cc(N)on1.O=C(Cl)OCC(Cl)(Cl)Cl>>Cc1cc(NC(=O)OCC(Cl)(Cl)Cl)on1 | null | C1CCOC1 | null | O | c1ccncc1 | train |
US20090137557A1 | BrC(Br)(Br)Br.COCc1nc(-c2ccccc2O)n(CCc2ccccc2)c(=O)c1Br>>O=c1c(Br)c(CBr)nc(-c2ccccc2O)n1CCc1ccccc1 | null | ClCCl | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | null | train |
US04006231 | CNC(=O)Oc1cccc2c1OC(C)(C)C2.ClSN1CCOCC1>>CN(SN1CCOCC1)C(=O)Oc1cccc2c1OC(C)(C)C2 | null | c1ccncc1 | null | Cl | O | train |
US20090169558A1 | CCOC(=O)c1cc(-c2ccnc(/C=C/c3cccnc3)c2)[nH]c1N.N=C(N)Cc1ccccc1>>O=c1[nH]c(Cc2ccccc2)nc2[nH]c(-c3ccnc(/C=C/c4ccccc4)c3)cc12 | null | CN(C)C=O | null | O=C([O-])[O-].[K+].[K+] | null | train |
US06169087A | CCOC=O.NCCCCCC(=O)O>>O=CCCCCCC(=O)O | null | CN(C)C=O | null | null | null | train |
US20110172230A1 | O=C(Nc1cncc(O)c1)N1CCN(C(=O)c2cccc(OCCC3CCCCC3)c2)CC1.OCCOCc1ccccc1>>O=C(Nc1cncc(OCCOCc2ccccc2)c1)N1CCN(C(=O)c2cccc(OCCC3CCCCC3)c2)CC1 | null | C1CCOC1 | O | CCOC(=O)/N=N/C(=O)OCC | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | train |
US20020120148A1 | CCOC(=O)COc1ccc2c(c1)CC(N(Cc1ccccc1)C(=O)OC(C)(C)C)CCC2>>CC(C)(C)OC(=O)N(Cc1ccccc1)C1CCCc2ccc(OCC(=O)O)cc2C1 | null | CCO | null | [Na+].[OH-] | null | train |
US20050043323A1 | CCOC(=O)CC(=O)Cl.CCOC(=O)CC(C)(C)N>>CCOC(=O)CC(=O)NC(C)(C)CC(=O)OCC | null | ClCCl | null | CCN(CC)CC | Cl | train |
US20110112298A1 | CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3ccccc3nc2-1>>CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)CC2Cc3ccccc3NC12 | [Ni] | CC(=O)O | null | [H][H] | null | train |
US20150018363A1 | Cc1c(C2CC2)nc2ccc(-n3ccc(O)cc3=O)cn12.OCc1ccsc1>>Cc1c(C2CC2)nc2ccc(-n3ccc(OCc4ccsc4)cc3=O)cn12 | null | C1CCOC1 | null | CCCCP(CCCC)CCCC | O=C(N=NC(=O)N1CCCCC1)N1CCCCC1 | train |
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