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 |
|---|---|---|---|---|---|---|---|
US20100273744A1 | CCO.Cc1ccc(C(=O)O)cc1C(F)(F)F>>CCOC(=O)c1ccc(C)c(C(F)(F)F)c1 | null | ClCCl | null | O | O=S(=O)(O)O | train |
US05344958 | CC(C)(C)NN.COc1cccc(C(=O)Cl)c1C>>COc1cccc(C(=O)NNC(C)(C)C)c1C | null | ClCCl | O | Cl | [Na+].[OH-] | train |
US20160051512A1 | CC(C)(C)OC(=O)N1CC[C@H](C(=O)O)C1.Cc1cc(N)ccc1F>>Cc1cc(NC(=O)[C@H]2CCN(C(=O)OC(C)(C)C)C2)ccc1F | null | ClCCl | null | CCN(C(C)C)C(C)C | CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F | train |
US04886835 | O=C(O)CBr.SCc1ccccc1>>O=C(O)CSCc1ccccc1 | null | C1CCOC1 | ClCCl | Cl | [Na+].[OH-] | train |
US20090325925A1 | CNC(=O)c1sc(N2CCOCC2)c(C#N)c1I.OB(O)c1ccc(Cl)cc1>>CNC(=O)c1sc(N2CCOCC2)c(C#N)c1-c1ccc(Cl)cc1 | c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | COCCOC | O | O=C([O-])[O-].[Na+].[Na+] | null | train |
US20100144695A1 | CC(C)(C)OC(=O)N1CC(NC(=O)CNC(=O)c2cccc(C(F)(F)F)c2)C1.O=S(=O)(O)O>>O=C(CNC(=O)c1cccc(C(F)(F)F)c1)NC1CNC1.O=S(=O)(O)O | null | CO | null | O=C([O-])O.[Na+] | null | train |
US20120232051A1 | CC(C)Oc1ncccc1B1OC(C)(C)C(C)(C)O1.CN(C(=O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1)c1cnccc1Br>>CC(C)Oc1ncccc1-c1ccncc1N(C)C(=O)c1cc(C(F)(F)F)cc(C(F)(F)F)c1 | null | CN(C)C=O | null | null | null | train |
US20150087585A1 | CC(C)(C)OC(=O)N1CCCC(C2=NCC3CCCN23)C1>>CC(C)(C)OC(=O)N1CCCC(c2ncc3n2CCC3)C1 | null | Cc1ccccc1 | null | null | null | train |
US20110053943A1 | COC(=O)C1(c2ccccc2)CCNCC1.O=C(Cl)OC1C2CC3CC(C2)CC1C3>>COC(=O)C1(c2ccccc2)CCN(C(=O)OC2C3CC4CC(C3)CC2C4)CC1 | null | CCOCC | ClCCl | CCN(C(C)C)C(C)C | Cl | train |
US05476945 | CCOS(=O)(=O)c1ccc(C)cc1.COc1ccc2nc(N)sc2c1>>CC[n+]1c(N)sc2cc(OC)ccc21.Cc1ccc(S(=O)(=O)[O-])cc1 | null | CC(C)=O | null | null | null | train |
US20050043347A1 | CNN.COc1cc(-c2csc3c(/C=C/C=O)cnc(N)c23)ccc1NC(=O)c1cc2ccccc2n1C>>COc1cc(-c2csc3c(C4CC=NN4C)cnc(N)c23)ccc1NC(=O)c1cc2ccccc2n1C | null | O | null | null | null | train |
US20050065178A1 | BrBr.c1ccc(-n2cccn2)cc1>>Brc1cnn(-c2ccccc2)c1 | null | CC(=O)O | null | O | O=C([O-])O.[Na+] | train |
US20140031364A1 | COC(=O)CC(C)=O.ON=C(Cl)c1ccccc1F>>COC(=O)c1c(-c2ccccc2F)noc1C | null | CO | null | C[O-].[Na+] | null | train |
US20060074119A1 | CON(C)C(=O)c1sc(-n2cnc3cc(Cl)ccc32)cc1OCc1ccccc1C.C[Mg]Br>>CC(=O)c1sc(-n2cnc3cc(Cl)ccc32)cc1OCc1ccccc1C | null | C1CCOC1 | null | null | null | train |
US20100137313A1 | Cc1nc(C)c(S(=O)(=O)Cl)s1.N>>Cc1nc(C)c(S(N)(=O)=O)s1 | null | ClC(Cl)Cl | null | C1CCOC1 | null | train |
US04098898 | Cc1nc[nH]c1CSCCN=C=S.NN>>Cc1nc[nH]c1CSCCNC(=S)NN | null | CCO | null | O | null | train |
US05189040 | Cc1nn(C)c(O)c1Sc1ccccc1Cl.Clc1ccnc(Cl)n1>>Cc1nn(C)c(Oc2ccnc(Cl)n2)c1Sc1ccccc1Cl | null | CC#N | null | O | O=C([O-])[O-].[K+].[K+] | train |
US07247645B2 | O=C(COCCCOCc1ccccc1)CC(=O)OCCC(c1ccccc1)c1ccccc1>>O=C(COCCCO)CC(=O)OCCC(c1ccccc1)c1ccccc1 | [Pd] | CCO | null | null | null | train |
US20110003833A1 | C[Si](C)(C)CCOCn1ccc(N)n1.Cc1cc(Cl)nc(Cl)n1>>Cc1cc(Nc2ccn(COCC[Si](C)(C)C)n2)nc(Cl)n1 | null | C1COCCO1 | CCOC(C)=O | CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21 | O=P([O-])([O-])[O-].[K+].[K+].[K+] | train |
US05260453 | O=C(NC1c2sccc2OCC1O)c1ccc(C(F)(F)F)cc1.O=[N+]([O-])O>>O=C(NC1C(O)=COC2=C1SC([N+](=O)[O-])C2)c1ccc(C(F)(F)F)cc1 | null | CC(=O)O | null | [Br-].[K+] | null | train |
US20030225147A1 | NCCNc1ccccc1.Nc1nc(Nc2ccc(C(=O)Oc3ccccc3)c(O)c2)sc1C(=O)c1c(F)cccc1F>>Nc1nc(Nc2ccc(C(=O)NCCNc3ccccc3)c(O)c2)sc1C(=O)c1c(F)cccc1F | null | CN(C)C=O | null | null | null | train |
US20130158026A1 | COC(=O)c1cc(C(C)Nc2cccc(Cl)c2F)c2oc(N3CCOCC3)cc(=O)c2c1>>CC(Nc1cccc(Cl)c1F)c1cc(C(=O)O)cc2c(=O)cc(N3CCOCC3)oc12 | null | CO | null | C1CCOC1 | [Na+].[OH-] | train |
US20130310358A1 | CC(C)(C)OC(=O)N1CC(F)(F)CC1C(=O)O>>CC(C)(C)OC(=O)N1CC(F)(F)C[C@H]1CO | null | C1CCOC1 | null | null | null | train |
US20100278833A1 | CN.C[C@@H](Oc1cc(-n2cnc3cc(COS(C)(=O)=O)ncc32)sc1C(N)=O)c1ccccc1C(F)(F)F>>CNCc1cc2ncn(-c3cc(O[C@H](C)c4ccccc4C(F)(F)F)c(C(N)=O)s3)c2cn1 | null | CO | null | null | null | train |
US20160075692A1 | N[C@@H]1CCOC1.O=C(O)CN1CCN(c2cccc3c2cnn3-c2ccccc2F)C1=O>>O=C(CN1CCN(c2cccc3c2cnn3-c2ccccc2F)C1=O)N[C@@H]1CCOC1 | 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 |
US20150045349A1 | Cc1cc(Cl)c(C#N)c(=O)n1-c1ccccc1Cl.O=C1CCC(=O)N1Br>>N#Cc1c(Cl)cc(CBr)n(-c2ccccc2Cl)c1=O | null | ClC(Cl)(Cl)Cl | ClCCl | CC(C)(C#N)N=NC(C)(C)C#N | null | train |
US20100316601A1 | CC1=NN(c2ccc3c(c2)CCO3)C(=O)C1.Cc1cc(N)c(O)c(-c2cccc(C(=O)O)c2)c1.O=N[O-]>>CC1=NN(c2ccc3c(c2)CCO3)C(=O)C1=NNc1cc(C)cc(-c2cccc(C(=O)O)c2)c1O | null | Cl | null | O=C([O-])O.[Na+] | null | train |
US06891066B2 | C[Si](C)(C)C#Cc1ccc(Nc2c(C(=O)O)ccc(F)c2F)c(F)c1>>C[Si](C)(C)C#Cc1ccc(N)c(F)c1 | null | CO | null | O=C([O-])[O-].[K+].[K+] | null | train |
US20080193700A1 | CC(=O)O.Cc1nc2ccc([N+](=O)[O-])cc2s1>>CC(=O)Nc1ccc2nc(C)sc2c1 | [Fe] | CC(=O)O | null | CC(=O)OC(C)=O | null | train |
US05739336 | CC(C)(C)NCC1(O)CCN(Cc2ccccc2)CC1.O=C(n1ccnc1)n1ccnc1>>CC(C)(C)N1CC2(CCN(Cc3ccccc3)CC2)OC1=O | null | C1CCOC1 | null | Cl | null | train |
US20110274846A1 | NCCCC[C@@H](C(=O)O)N(CC(=O)O)CC(=O)O>>NCCCCC(C(=O)O)N(CC(=O)O)CC(=O)O | null | CS(C)=O | null | ClCCCl | null | train |
US20020049240A1 | Clc1nc2ccccc2s1.OCCNCc1ccccc1>>OCCN(Cc1ccccc1)c1nc2ccccc2s1 | null | CCOC(C)=O | null | null | null | train |
US07504412B2 | Cc1c(C2CC2)nc2ccc([N+](=O)[O-])cn12.Cl.O=C(O)c1ccc(-c2ccc(F)cc2)cn1>>Cc1c(C2CC2)nc2ccc(NC(=O)c3ccc(-c4ccc(F)cc4)cn3)cn12.Cl | null | CCOC(C)=O | null | null | null | train |
US20130109689A1 | CCN1CC(CCN2CCOCC2)C(c2ccccc2)(c2ccccc2)C1=O>>CCN1CC(CCN2CCOCC2)C(c2ccccc2)(c2ccccc2)C1=O | null | ClCCl | null | Cl | O=C([O-])O.[Na+] | train |
US20140235620A1 | CC(C)C1COC(=O)N1c1ccnc(N[C@@H](C)C2CCNCC2)n1.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O>>CC(C)[C@H]1COC(=O)N1c1ccnc(N[C@@H](C)C2CCN(C(=O)c3ccncc3)CC2)n1 | null | ClCCl | null | CCN(C(C)C)C(C)C | null | train |
US20030036557A1 | CS(=O)(=O)c1ccc(N)cc1.Cc1cccc(C#N)n1>>Cc1cccc(C(=N)Nc2ccc(S(C)(=O)=O)cc2)n1 | null | Cc1ccccc1 | ClC(Cl)Cl | C[Al](C)C | Cl | train |
US05317023 | CC(C)(C)OC(=O)Nc1ccccc1-c1oc2ccc(CBr)cc2c1Br.CCc1nc2c(C)cc(C)nc2[nH]1>>CCc1nc2c(C)cc(C)nc2n1Cc1ccc2oc(-c3ccccc3NC(=O)OC(C)(C)C)c(Br)c2c1 | null | CN(C)C=O | null | O | [H-].[Na+] | train |
US05665718 | O=C1c2ccccc2C(=O)N1Cc1nnc(-c2ncn3c2[C@@H]2CCN2C(=O)c2sccc2-3)o1>>NCc1nnc(-c2ncn3c2[C@@H]2CCN2C(=O)c2sccc2-3)o1 | null | CCO | null | CN | null | train |
US05684011 | FC(CCBr)C(F)(F)Br.FC(F)(F)COc1cc(=S)[nH]cn1>>FC(CCSc1cc(OCC(F)(F)F)ncn1)C(F)(F)Br | null | CC(C)=O | null | O=C([O-])[O-].[K+].[K+] | null | train |
US20100010090A1 | CCOC(=O)c1ccc(O)cc1.ClI>>CCOC(=O)c1ccc(O)c(I)c1 | null | CC(=O)O | null | null | null | train |
US20010011143A1 | O=S(=O)([O-])c1ccc(Oc2ccc(F)cc2)cc1.O=S(Cl)Cl>>O=S(=O)(Cl)c1ccc(Oc2ccc(F)cc2)cc1 | null | Cc1ccccc1 | null | CN(C)C=O | null | train |
US20100256101A1 | COc1c(C)c2c(c(C)c1OC)C(CC(N)=O)NCC2>>COc1c(C)c2c(c(C)c1OC)CNCC2 | null | C1COCCO1 | null | [Na+].[OH-] | null | train |
US20160122341A1 | CCCC[C@@H](N)CO.Cc1nc2c(OCc3c(F)cccc3F)cc(Cl)cn2c1C(=O)O>>CCCC[C@H](CO)NC(=O)c1c(C)nc2c(OCc3c(F)cccc3F)cc(Cl)cn12 | 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 |
US05166198 | CCOP(=O)(CCCCO[Si](C)(C)C(C)(C)C)OCC>>CCOP(=O)(CCCCO)OCC | null | CC(=O)O | null | O | null | train |
US20100105700A1 | CN1C(=O)CC[C@@]2(C)C1=CC[C@H]1[C@@H]3CC=C(OS(=O)(=O)C(F)(F)F)[C@@]3(C)CC[C@@H]12.OB(O)c1cnccc1Cl>>CN1C(=O)CC[C@@]2(C)C1=CC[C@H]1[C@@H]3CC=C(c4cnccc4Cl)[C@@]3(C)CC[C@@H]12 | Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1 | C1COCCO1 | null | null | null | train |
US20110105514A1 | CC(C)(C)OC(=O)N1CCn2c(C3CC3)nc(I)c2C1CCc1ccc(F)c(C(F)(F)F)c1>>CC(C)(C)OC(=O)N1CCn2c(cnc2C2CC2)C1CCc1ccc(F)c(C(F)(F)F)c1 | [Pd] | CO | ClCCl | O | O=C([O-])[O-].[K+].[K+] | train |
US20070208007A1 | CCCN(CCC)CCCCN1Cc2cc(CNCc3ncc[nH]3)ccc2C1=O.Cn1ccnc1C=O>>CCCN(CCC)CCCCN1Cc2cc(CN(Cc3ncc[nH]3)Cc3nccn3C)ccc2C1=O | null | CC(=O)O | CO | [BH3-]C#N.[Na+] | null | train |
US20150072969A1 | BrC(Br)(Br)Br.OCc1cccc(-c2ccc(C(F)(F)F)cc2)c1>>FC(F)(F)c1ccc(-c2cccc(CBr)c2)cc1 | null | ClCCl | null | null | null | train |
US04615966 | BrBr.CC(=O)N1CCc2ccccc21>>CC(=O)N1CCc2cc(Br)ccc21 | null | CC(=O)O | null | O=S([O-])O.[Na+] | null | train |
US20080004297A1 | CI.COc1ccc(Nc2nc(C)nc3ccc([N+](=O)[O-])cc23)cc1OC>>COc1ccc(N(C)c2nc(C)nc3ccc([N+](=O)[O-])cc23)cc1OC | null | CN(C)C=O | null | [H-].[Na+] | null | train |
US06002008 | COc1cccc2c(Cl)c(C#N)cnc12.Nc1cccc(Br)c1>>COc1cccc2c(Nc3cccc(Br)c3)c(C#N)cnc12 | null | CCOCCO | null | Cl | c1ccncc1 | train |
US05219863 | CCOC(=O)COc1ccc2nc(CC)cc(OCc3ccc(-c4ccccc4-c4nnn(C(c5ccccc5)(c5ccccc5)c5ccccc5)n4)cc3)c2n1.Cl>>Cl.c1cnc2cccnc2c1 | null | CCO | null | null | null | train |
US20120115895A1 | CC(C)c1nc(CN2C(=O)N(C)C3(C2=O)C(=O)N(CC(=O)OC(C)(C)C)c2ccc(Cl)cc23)cs1>>CC(C)c1nc(CN2C(=O)N(C)C3(C2=O)C(=O)N(CC(=O)O)c2ccc(Cl)cc23)cs1 | null | C1COCCO1 | Cl | null | null | train |
US20110152240A1 | CC(C)(C)OC(=O)N1CCN(C(=O)c2cccc(Nc3cc(Nc4cccc(Cl)c4)nc4c(C=C5NC(=O)NC5=O)cnn34)c2)CC1>>O=C1NC(=O)C(=Cc2cnn3c(Nc4cccc(C(=O)N5CCNCC5)c4)cc(Nc4cccc(Cl)c4)nc23)N1 | null | ClCCl | O=C(O)C(F)(F)F | null | null | train |
US20020013480A1 | CCCc1cc(=O)oc2cc(OC(=O)CC)c3c(c12)OC(C)(C)C=C3>>CCCc1cc(=O)oc2cc(O)c3c(c12)OC(C)(C)C=C3 | null | CO | null | O | O=C([O-])O.[Na+] | train |
US20110224204A1 | Cc1ccc(OC2CCCCO2)c(-c2ccc(OCc3ccc4ccccc4n3)cc2)c1>>Cc1ccc(O)c(-c2ccc(OCc3ccc4ccccc4n3)cc2)c1 | null | CO | ClCCl | Cc1ccc(S(=O)(=O)[O-])cc1.c1cc[nH+]cc1 | null | train |
US20120289549A1 | NS(=O)(=O)c1ccccc1Cl.O=C1N(c2ccc(OCC(F)(F)F)cc2)C[C@H]2C[C@@H](Br)CN12>>O=C1N(c2ccc(OCC(F)(F)F)cc2)C[C@H]2C[C@H](NS(=O)(=O)c3ccccc3Cl)CN12 | null | CN(C)C=O | null | O=C([O-])[O-].[K+].[K+] | null | train |
US06124281 | Cc1ccc(S(=O)(=O)NN=Cc2ccccc2)cc1>>[N-]=[N+]=Cc1ccccc1 | null | CO | null | C[O-].[Na+] | null | train |
US20100144745A1 | Cc1ccc(S(=O)(=O)Cl)cc1.OCC1(C(F)(F)F)CC1>>Cc1ccc(S(=O)(=O)OCC2(C(F)(F)F)CC2)cc1 | CN(C)c1ccncc1 | ClCCl | null | CCN(CC)CC | null | train |
US06180835B2 | C#CC(C)(C)OC1CCCO1.ClCCCBr>>CC(C)(C#CCCCCl)OC1CCCO1 | null | C1CCOC1 | CN(C)P(=O)(N(C)C)N(C)C | [Li]CCCC | [Cl-].[NH4+] | train |
US20090143353A1 | Cc1c(-c2ccccc2)c(N2CC[C@H](N(C)C)C2)c2oc(C(C)(C)COCc3ccccc3)nc2c1C#N.Cl>>Cc1c(-c2ccccc2)cc2ocnc2c1C#N.Cl | null | CCOCC | null | C1COCCO1 | null | train |
US20150274661A1 | CC(C)Br.O=C(Nc1cccc(F)c1)c1cc2cc(-c3cccnc3)ccc2[nH]1>>CC(C)N1CCCC(c2ccc3[nH]c(C(=O)Nc4cccc(F)c4)cc3c2)C1 | null | CN(C)C=O | null | null | null | train |
US20040102384A1 | CC(C)(C)OC(=O)CN1CCN(CC(=O)OC(C)(C)C)C1=O>>CC(C)(C)OC(=O)CN1CCN(CC(=O)O)C1=O | null | CCO | O | [K+].[OH-] | null | train |
US06017917 | CC(C)OB(OC(C)C)OC(C)C.Clc1ccc(Cl)c(I)c1>>OB(O)c1cc(Cl)ccc1Cl | null | C1CCOC1 | CCCCCC | Cl | [Li]CCCC | train |
US20080207616A1 | COC(=O)c1cc(C#CCO)cc(C(C)(C)C#N)c1>>CCCc1cc(C(=O)OC)cc(C(C)(C)C#N)c1 | [Pd] | CO | null | null | null | train |
US04311787 | CCOC(=O)C1=NN(c2ccc(C(=O)O)cc2)C(=O)C1.O=Cc1ccc(O)cc1>>CCOC(=O)C1=NN(c2ccc(C(=O)O)cc2)C(=O)C1=Cc1ccc(O)cc1 | null | CC(=O)O | null | null | null | train |
US20110190618A1 | CCN(CC)C(=O)C1Sc2ccccc2-c2[nH]c3ccc(OC)cc3c21.Cc1ccc(S(=O)(=O)OCCF)cc1>>CCN(CC)C(=O)C1Sc2ccccc2-c2c1c1cc(OC)ccc1n2CCF | null | CN(C)C=O | null | [H-].[Na+] | null | train |
US20070286810A1 | C=C(C)C(=O)Cl.CC(=O)c1cccc(N)c1>>C=C(C)C(=O)Nc1cccc(C(C)=O)c1 | null | c1ccncc1 | null | null | null | train |
US20110021511A1 | NC(=O)c1[nH]c2cc(Br)cc(F)c2c1N.O=C(Cl)OC(Cl)(Cl)Cl>>O=c1[nH]c(=O)c2[nH]c3cc(Br)cc(F)c3c2[nH]1 | null | C1COCCO1 | null | O | null | train |
US04935430 | Cc1nc2cnccc2[nH]1.OO>>Cc1[nH]c2cnccc2[n+]1[O-] | null | CC(=O)O | null | null | null | train |
US20040127534A1 | CCOC(C)=O.CN(C)C=O.CN(C)c1ccncc1.C[C@@]1(Cc2ccc(C#N)cc2)C(=O)N(c2cc(Cl)cc(Cl)c2)c2ncc(S(=O)(=O)Cl)n21>>C[C@H](NS(=O)(=O)c1cnc2n1[C@](C)(Cc1ccc(C#N)cc1)C(=O)N2c1cc(Cl)cc(Cl)c1)C(=O)NCCO | CN(C)c1ccncc1 | CN(C)C=O | null | null | null | train |
US20160016979A1 | COC(=O)[C@H](CO)NC(=O)OC(C)(C)C.NCCN>>CC(C)(C)OC(=O)N[C@@H](CO)C(=O)NCCN | null | Cc1ccccc1 | null | null | null | train |
US20110021573A1 | CCO.COc1ccc(CC(=O)O)cc1Br>>CCOC(=O)Cc1ccc(OC)c(Br)c1 | Cl | null | null | null | null | train |
US20130143862A1 | CC(C)(C)OC(=O)N(CC1(c2ncccc2F)CCC1)c1ccc(F)nn1.N#Cc1cc[nH]c1>>CC(C)(C)OC(=O)N(CC1(c2ncccc2F)CCC1)c1ccc(-n2ccc(C#N)c2)nn1 | null | CN(C)C=O | null | CCOC(C)=O | O=C([O-])[O-].[K+].[K+] | train |
US20070066647A1 | Cc1cc2c(cc1Br)C(C)(C)CCC2(C)C.O=C1CCC(=O)N1Br>>CC1(C)CCC(C)(C)c2cc(CBr)c(Br)cc21 | null | ClC(Cl)(Cl)Cl | null | CC(C)(C#N)N=NC(C)(C)C#N | null | train |
US05180735 | COC1CC(O)(CSC)C(C2(C)OC2CC=C(C)C)CC1O.O=C=NC(=O)CCl>>COC1C(OC(=O)NC(=O)CCl)CCC(O)(CSC)C1C1(C)OC1CC=C(C)C | null | ClCCl | null | CCOC(C)=O | null | train |
US06316500B1 | C#CCBr.O=C(O)c1ccc(O)c(O)c1>>C#CCOC(=O)c1ccc(O)c(O)c1 | null | CC(C)O | null | [Na+].[OH-] | null | train |
US20020004513A1 | CC(C)(C)OC(=O)N1CCC(=O)CC1.NCCCc1ccccc1>>CC(C)(C)OC(=O)N1CCC(NCCCc2ccccc2)CC1 | null | CO | O | CC(=O)O | [BH3-]C#N.[Na+] | train |
US20050222118A1 | COc1cccc(N=C=O)c1.NCCCN1CC(Oc2ccc(F)cc2)C1>>COc1cccc(NC(=O)NCCCN2CC(Oc3ccc(F)cc3)C2)c1 | null | C1COCCO1 | null | null | null | train |
US20080312227A1 | CC(C)(C)C(=O)Nc1nc(-c2nc[nH]n2)c2cc(Br)cnc2n1.Cc1cccc(N)c1>>Cc1cccc(Nc2nc(NC(=O)C(C)(C)C)nc3ncc(Br)cc23)c1 | null | C1COCCO1 | null | O | null | train |
US07081461B1 | Cc1ccnc(COc2ccc([N+](=O)[O-])cc2C)c1>>Cc1ccnc(COc2ccc(N)cc2C)c1 | [Pt] | CCO | null | null | null | train |
US20090149425A1 | CC(C)c1cc(C(C)O)no1.Cc1ccc(S(=O)(=O)Cl)cc1>>CC(C)c1cc(C(C)Cl)no1 | null | c1ccncc1 | null | O | null | train |
US20150011548A1 | CC(=O)Nc1cc(-n2cccc2)cc(-n2cnc3cc(-c4cnn(C)c4)ccc32)c1>>Cn1cc(-c2ccc3c(c2)ncn3-c2cc(N)cc(-n3cccc3)c2)cn1 | null | CCO | CCOC(C)=O | [Na+].[OH-] | null | train |
US03943141 | Nc1nnn[nH]1.O=C(O)c1c[nH]c2nc(Cl)ccc2c1=O>>O=C(Nc1nnn[nH]1)c1c[nH]c2nc(Cl)ccc2c1=O | null | CN(C)C=O | null | null | null | train |
US04374131 | CC(C)(C)C(=O)OCCl.O=C(NC(CCCc1ccccc1)P(=O)(O)CC(=O)N1CCC[C@H]1C(=O)OCc1ccccc1)c1ccccc1>>CC(C)(C)C(=O)OCOP(=O)(CC(=O)N1CCC[C@H]1C(=O)OCc1ccccc1)C(CCCc1ccccc1)NC(=O)c1ccccc1 | null | CCOC(C)=O | CN(C)C=O | CCN(CC)CC | null | train |
US03996229 | COc1ccc2c(c1)Sc1ccc(SC)cc1C(=O)C2>>COc1ccc2c(c1)Sc1ccc(SC)cc1C(O)C2 | null | O | null | CCO | [BH4-].[Na+] | train |
US20020035136A1 | CCOC(=O)C(=O)N(Cc1ccccc1)CC(c1ccc(-c2cccc3ccccc23)cc1)C1CCCCC1>>O=C(O)C(=O)N(Cc1ccccc1)CC(c1ccc(-c2cccc3ccccc23)cc1)C1CCCCC1 | null | CCO | null | Cl | [Na+].[OH-] | train |
US20140275111A1 | CCOc1cc(Br)cnc1Cl.COc1ccc(CO)cc1>>CCOc1cc(Br)cnc1OCc1ccc(OC)cc1 | null | CN(C)C=O | null | [H-].[Na+] | null | train |
US03962249 | CC1CN(CCCc2ccccc2)CCN1.Cc1ccc(C(=O)Cl)o1>>Cc1ccc(C(=O)N2CCN(CCCc3ccccc3)CC2C)o1.Cl | null | c1ccccc1 | null | null | null | train |
US20070021404A1 | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.OC1CCNCC1>>CC(C)(C)OC(=O)N1CCC(O)CC1 | null | ClCCl | null | O=C([O-])O.[Na+] | null | train |
US20090099158A1 | C1CCNCC1.O=Cc1ccc2c(c1)CCN(C(=O)C1CCCCC1)C2>>O=C(C1CCCCC1)N1CCc2cc(CN3CCCCC3)ccc2C1 | null | ClCCCl | null | CC(=O)O | CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+] | train |
US20070078121A1 | NC=O.Nc1ccc([N+](=O)[O-])cc1C(=O)O>>O=c1[nH]cnc2ccc([N+](=O)[O-])cc12 | null | O | null | null | null | train |
US20100130506A1 | COC(=O)c1ccc2cc(OC[C@@H](O)CO)ccc2c1.COC(C)(C)OC>>COC(=O)c1ccc2cc(OC[C@@H]3COC(C)(C)O3)ccc2c1 | null | CN(C)C=O | null | Cc1ccc(S(=O)(=O)[O-])cc1.c1cc[nH+]cc1 | null | train |
US20030191337A1 | CC(O)(CSc1ccc(F)cc1)C(=O)Nc1ccc(C#N)c(C(F)(F)F)c1.O=C(O)c1ccccc1C(=O)OO>>CC(O)(CS(=O)(=O)c1ccc(F)cc1)C(=O)Nc1ccc(C#N)c(C(F)(F)F)c1 | null | CCOC(C)=O | null | [K+].[OH-] | null | train |
US20070129419A1 | CC(C)(C)OC(=O)N1CC(COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)C(c2ccc(F)cc2)C1.Cl>>Cl.Fc1ccc(C2CNCC2COCc2cc(C(F)(F)F)cc(C(F)(F)F)c2)cc1 | null | CO | null | null | null | train |
US20140213578A1 | Clc1ccc2c(c1)Nc1ccccc1CC2.O=C(Cl)CCl>>O=C(CCl)N1c2ccccc2CCc2ccc(Cl)cc21 | null | Cc1ccccc1 | null | null | null | train |
US20030109607A1 | O=C=NC1CCC(CC2CCC(N=C=O)CC2)CC1.O=C=NC1CCCCC1>>CCCCCCCCN | null | C1CCOC1 | null | null | null | train |
US20030225131A1 | Nc1cccc2oc(NCc3cccc(Cl)c3)nc12.O=S(=O)(OCC(F)(F)c1ccccn1)C(F)(F)F>>FC(F)(CNc1cccc2oc(NCc3cccc(Cl)c3)nc12)c1ccccn1 | null | CC(=O)N(C)C | null | CCN(C(C)C)C(C)C | null | train |
US20110201640A1 | COCC(=O)Cl.Nc1cccc(Cl)c1[N+](=O)[O-]>>COCC(=O)Nc1cccc(Cl)c1[N+](=O)[O-] | null | ClCCl | null | CCN(CC)CC | Cl | train |
US20100234351A1 | CC(C)(C)NC(=O)c1cccc(Oc2ccc(N)cc2Cl)c1.COc1ccc(CN(CCCC(=O)OC(C)(C)C)c2ncnc(Cl)c2C=O)cc1>>COc1ccc(CN(CCCC(=O)OC(C)(C)C)c2ncnc(Nc3ccc(Oc4cccc(C(=O)NC(C)(C)C)c4)c(Cl)c3)c2C=O)cc1 | null | CN(C)C=O | null | O | O=C([O-])[O-].[Na+].[Na+] | train |
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