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 |
|---|---|---|---|---|---|---|---|
US20120028919A1 | CI.O=c1[nH]c(=S)[nH]n2cc(Br)cc12>>CSc1nn2cc(Br)cc2c(=O)[nH]1 | null | C1CCOC1 | null | null | null | train |
US20150225449A1 | CC(=O)c1ccc(C(=O)N2c3ccccc3NC(=O)[C@@H](NC(=O)[C@H](C)N(C)C(=O)OC(C)(C)C)[C@@H]2C)cc1.COc1ccc2c(Br)cccc2c1CCl>>COc1ccc2c(Br)cccc2c1CN1C(=O)[C@@H](NC(=O)[C@H](C)N(C)C(=O)OC(C)(C)C)[C@H](C)N(C(=O)c2ccc(C(C)=O)cc2)c2ccccc21 | null | CN(C)C=O | O | [I-].[Na+] | O=C([O-])[O-].[Cs+].[Cs+] | train |
US20040132769A1 | COc1cccc(B(O)O)c1.Nc1c(F)c(F)c(Br)c(F)c1F>>COc1cccc(-c2c(F)c(F)c(N)c(F)c2F)c1 | null | COCCOC | null | c1ccc(P(c2ccccc2)c2ccccc2)cc1 | O=C([O-])[O-].[K+].[K+] | train |
US20110144105A1 | CN(C)c1ccc(C(=CC2CCCC2)c2cc3cccnc3[nH]2)cc1>>CN(C)c1ccc(C(CC2CCCC2)c2cc3cccnc3[nH]2)cc1 | [Pd] | CO | null | null | null | train |
US20070155726A1 | C=O.COC(=O)c1ccc(CNCC2CCCN2C(=O)OC(C)(C)C)cc1>>COC(=O)c1ccc(CN(C)CC2CCCN2C(=O)OC(C)(C)C)cc1 | null | CC(Cl)Cl | null | CC(=O)O | O=C([O-])O.[Na+] | train |
US04772614 | CI.Oc1ccnc2cc(F)ccc12>>Cn1ccc(=O)c2ccc(F)cc21 | null | CN(C)C=O | null | O | O=C([O-])[O-].[K+].[K+] | train |
US20060122187A1 | CC(C)CN1CCN(c2ccc([N+](=O)[O-])cn2)CC1>>CC(C)CN1CCN(c2ccc(N)cn2)CC1 | [Pd] | CO | null | [H][H] | null | train |
US20070249637A1 | COC(=O)[C@@H]1C[C@@H](Oc2nc(-c3cc(C)nn3C)nc3ccsc23)CN1C(=O)OC(C)(C)C>>Cc1cc(-c2nc(O[C@@H]3C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)C3)c3sccc3n2)n(C)n1 | null | CO | null | C1CCOC1 | [Li+].[OH-] | train |
US20020094987A1 | COc1cccc2c1nc(C(F)(F)F)n2C.O=C1CCC(=O)N1Br>>COc1ccc(Br)c2c1nc(C(F)(F)F)n2C | null | ClC(Cl)Cl | null | null | null | train |
US04420615 | CC(C)N(CCN)C(C)C.Cc1cc(C)c(C#N)c(Cl)n1>>Cc1cc(C)c(C#N)c(NCCN(C(C)C)C(C)C)n1 | null | CCN(CC)CC | null | null | null | train |
US04420424 | CC(=O)O.CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CCCCN)NC(=O)OCc1ccccc1)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)O>>CC(=O)O.COC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](N)CCCCN)C(C)C | null | O | null | null | null | train |
US20080318923A1 | COc1ccc(S(=O)(=O)N2C(=O)C(O)(c3ccccc3OC)c3cc(Cl)ccc32)c(OC(F)(F)F)c1.O=S(Cl)Cl>>COc1ccc(S(=O)(=O)N2C(=O)C(Cl)(c3ccccc3OC)c3cc(Cl)ccc32)c(OC(F)(F)F)c1 | null | ClC(Cl)Cl | null | null | null | train |
US20070254937A1 | CC(C)(C)OC(=O)n1nc(-c2c(Br)c3ccc(O[Si](C)(C)C(C)(C)C)cc3n2C(=O)OC(C)(C)C)c2sccc21>>CC(C)(C)OC(=O)n1nc(-c2c(Br)c3ccc(O)cc3n2C(=O)OC(C)(C)C)c2sccc21 | null | C1CCOC1 | null | CCCC[N+](CCCC)(CCCC)CCCC.[F-] | null | train |
US20160024044A1 | N#CCc1ccc(Br)c(Cl)c1.O=Cc1ccccc1>>N#CC(c1ccc(Br)c(Cl)c1)C(O)c1ccccc1 | null | C1CCOC1 | null | CC(C)[N-]C(C)C.[Li+] | null | train |
US20150152067A1 | CN1CCOCC1.C[C@H](CC(=O)O)c1c(I)ncnc1N1CCN(C(=O)OC(C)(C)C)CC1.O.O=C(n1ccnc1)n1ccnc1>>CON(C)C(=O)C[C@@H](C)c1c(I)ncnc1N1CCN(C(=O)OC(C)(C)C)CC1 | null | C1CCOC1 | O | [Cl-].[NH4+] | null | train |
US20140163001A1 | CC(C)(C)n1ncc(C2=NC(C(=O)O)CS2)c1-c1ccc(F)cc1.NCC1CCOCC1>>CC(C)(C)n1ncc(C2=NC(C(=O)NCC3CCOCC3)CS2)c1-c1ccc(F)cc1 | null | CN(C)C=O | O | CCN(C(C)C)C(C)C | CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F | train |
US20160221945A1 | CC1(F)C[C@@H](C(=O)NCc2cc(-c3ccc(C(F)(F)F)nc3)ncn2)N(C(=O)OC(C)(C)C)C1.Cl>>CC1(F)CN[C@H](C(=O)NCc2cc(-c3ccc(C(F)(F)F)nc3)ncn2)C1.Cl | null | C1COCCO1 | null | null | null | train |
US20100298290A1 | COc1cc2nc[nH]c(=O)c2cc1Br.O=S(Cl)Cl>>COc1cc2ncnc(Cl)c2cc1Br | null | CN(C)C=O | null | null | null | train |
US20060178377A1 | CC(=O)C(=Cc1ccc(Cl)c(F)c1)C(N)=O.COc1ccccc1-c1c[nH]c(N)n1>>COc1ccccc1-c1cn2c(n1)NC(C)=C(C(N)=O)C2c1ccc(Cl)c(F)c1 | null | C1CCOC1 | CO | CC(=O)[O-].[Na+] | null | train |
US20100240688A1 | CCCCBr.O=c1cc(OCc2ccccc2)cc[nH]1>>CCCCn1ccc(OCc2ccccc2)cc1=O | null | CC#N | null | O=C([O-])[O-].[K+].[K+] | null | train |
US20100075948A1 | CC(C)(C)CC1NC(C(=O)O)C(c2cccc(Cl)c2)C1(C#N)c1ccc(Cl)cc1.CC(C)(C)CN>>CC(C)(C)CNC(=O)C1NC(CC(C)(C)C)C(C#N)(c2ccc(Cl)cc2)C1c1cccc(Cl)c1 | 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 |
US20020193382A1 | CC(=O)O.CO.NCCNS(=O)(=O)c1ccc2cc(Cl)ccc2c1.O=Cc1ccc(-n2ccnc2)cc1>>O=C1CN(S(=O)(=O)c2ccc3cc(Cl)ccc3c2)CCN1Cc1ccc(-n2ccnc2)cc1 | null | CO | null | Cl | CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+] | train |
US20090062290A1 | O=C(Nc1nc2ccc(F)cn2c1-c1ccccc1)C(F)(F)F>>Nc1nc2ccc(F)cn2c1-c1ccccc1 | null | CO | O | O=C([O-])[O-].[K+].[K+] | null | train |
US20080242685A1 | CC(C)(C)OC(=O)N1CCC(=Cc2ncncc2[N+](=O)[O-])CC1>>CC(C)(C)OC(=O)N1CCC(Cc2ncncc2N)CC1 | [Pd] | CO | null | null | null | train |
US05733912 | CCc1cc(C23CCCN2CCC3)on1.Cl>>CCc1cc(C23CCCN2CCC3)on1.Cl | null | CCOCC | null | null | null | train |
US05354758 | CI.Cc1ccncc1C>>Cc1cc[n+](C)cc1C.[I-] | null | CC(C)=O | null | null | null | train |
US20120010235A1 | C=O.COC(=O)[C@@H]1N[C@@H](CC(C)(C)C)[C@](C#N)(c2ccc(Cl)cc2F)[C@H]1c1cccc(Cl)c1F>>COC(=O)[C@H]1[C@H](c2cccc(Cl)c2F)[C@@](C#N)(c2ccc(Cl)cc2F)[C@H](CC(C)(C)C)N1C | null | CC(=O)O | O | CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+] | null | train |
US20140140956A1 | CN1CC[C@H](O)C1.CS(=O)(=O)c1ccc(-c2cccc(-c3nc4cc(F)cc(F)c4c(=O)[nH]3)n2)cc1>>CN1CC[C@H](Oc2cc(F)cc3nc(-c4cccc(-c5ccc(S(C)(=O)=O)cc5)n4)[nH]c(=O)c23)C1 | null | CN(C)C=O | O | Cl | [H-].[Na+] | train |
US20120258952A1 | Cc1cccc(CBr)n1.O=[N+]([O-])c1cccc2[nH]nc(I)c12>>Cc1cccc(Cn2nc(I)c3c([N+](=O)[O-])cccc32)n1 | null | CN(C)C=O | O | O=C([O-])[O-].[K+].[K+] | null | train |
US20100216839A1 | CCOP(=O)(NC1CNCCC1Cl)OCC.O=[N+]([O-])c1cnccc1Cl>>CCOP(=O)(NC1CN(c2ccncc2[N+](=O)[O-])CCC1Cl)OCC | null | CC(C)O | null | CCN(C(C)C)C(C)C | null | train |
US20150031689A1 | NCC1CCC(CNc2ncnc3c2nc(-c2ccccc2Cl)n3-c2ccc(Cl)cc2)CC1.NS(N)(=O)=O>>O=[SH](=O)NNCC1CCC(CNc2ncnc3c2nc(-c2ccccc2Cl)n3-c2ccc(Cl)cc2)CC1 | null | C1COCCO1 | null | null | null | train |
US20100292188A1 | CC(=O)N1CCc2nc(-c3ccc(O)c(F)c3)sc2C1.O=S(=O)(O[C@@H]1C[C@H](N2CCCCC2)C1)c1ccc(Br)cc1>>CC(=O)N1CCc2nc(-c3ccc(O[C@@H]4C[C@@H](N5CCCCC5)C4)c(F)c3)sc2C1 | null | C1CCOC1 | O | C1COCCOCCOCCOCCO1 | [H-].[Na+] | train |
US05272163 | CC(O)(C(=O)O)C(F)(F)F.N#Cc1ccccc1S(=O)(=O)c1ccc(N)cc1>>CC(O)(C(=O)Nc1ccc(S(=O)(=O)c2ccccc2C#N)cc1)C(F)(F)F | null | CC(=O)N(C)C | null | O | O=S(Cl)Cl | train |
US05523302 | CC(=O)c1cccc(O)c1.OCCBr>>CC(=O)c1cccc(OCCO)c1 | null | CCOC(C)=O | CN(C)C=O | [I-].[K+] | O=C([O-])O.[Na+] | train |
US20100197591A1 | CC(C)(C)[Mg]Cl.O=Cc1ccc(Br)cc1>>CC(C)(C)C(O)c1ccc(Br)cc1 | null | C1CCOC1 | null | [Cl-].[NH4+] | null | train |
US20080146567A1 | O=C(Cl)c1cc(F)cc(F)c1.O=[N+]([O-])c1cccc2nc(N[C@@H]3CCc4ccccc43)ccc12>>O=C(Nc1cccc2nc(N[C@@H]3CCc4ccccc43)ccc12)c1cc(F)cc(F)c1 | null | c1ccncc1 | null | Cl | null | train |
US20090069288A1 | COC(=O)c1c(-c2ccc(Cl)cc2)csc1N.O=C(Cl)c1ccccc1>>COC(=O)c1c(-c2ccc(Cl)cc2)csc1NC(=O)c1ccccc1 | null | CC#N | null | c1ccncc1 | null | train |
US20130281412A1 | COc1ccc(C(=O)Nc2ccc(F)cc2F)c(O)c1.Fc1ccc(CBr)c(F)c1>>COc1ccc(C(=O)Nc2ccc(F)cc2F)c(OCc2ccc(F)cc2F)c1 | null | CC(C)=O | null | O=C([O-])[O-].[K+].[K+] | null | train |
US20130244993A1 | CS(C)(=O)=O.Fc1ccc(Br)cn1>>CS(=O)(=O)Cc1ccc(Br)cn1 | null | C1CCOC1 | null | C[Si](C)(C)[N-][Si](C)(C)C.[Na+] | null | train |
US20030216325A1 | CC1(C)C=CC(=O)CC1>>CC1(C)CCC(=O)CC1 | [Pd] | null | null | null | null | train |
US20040138286A1 | C=O.Cc1c(O[C@@H]2CCC[C@H](NCc3ccccc3)C2)ccc2[nH]ncc12>>Cc1c(O[C@@H]2CCC[C@H](N(C)Cc3ccccc3)C2)ccc2[nH]ncc12 | null | CO | ClC(Cl)Cl | CC(=O)O | [BH3-]C#N.[Na+] | train |
US20110288097A1 | CC(C)(O)C1(NC(=O)c2cn(COCC[Si](C)(C)C)c3ncc(C4CC4)nc23)CCCC1>>CC(C)(O)C1(NC(=O)c2c[nH]c3ncc(C4CC4)nc23)CCCC1 | null | ClCCl | null | O=C(O)C(F)(F)F | null | train |
US05010083 | CN.COc1ccc2c(c1)C(CC=O)CC(=O)N2C>>CNCCC1CC(=O)N(C)c2ccc(OC)cc21 | null | CO | null | Cl | [BH3-]C#N.[Na+] | train |
US20110143149A1 | CC(=O)O.CO[Si](CCCN(C)C)(OC)OC>>CC(=O)[O-].CO[Si](CCC[NH+](C)C)(OC)OC | null | CO | null | null | null | train |
US20150072980A1 | COc1cc2c(cc1N1CCC(C)CC1)C/C(=C\c1cccc(C(F)(F)F)c1)C2=O>>COc1cc2c(cc1N1CCC(C)CC1)CC(Cc1cccc(C(F)(F)F)c1)C2=O | [Ni] | CO | null | null | null | train |
US20150011773A1 | CC(C)(C)OC(=O)N[C@@H](CC(CCCc1ccc(CCCF)cc1)C(=O)OC(C)(C)C)C(=O)OC(C)(C)C>>N[C@@H](CC(CCCc1ccc(CCCF)cc1)C(=O)O)C(=O)O | null | O=C(O)C(F)(F)F | null | Cc1ccccc1 | null | train |
US20080045506A1 | CC(C)N1CCN(C(=O)[C@H]2CCN(C(=O)OC(C)(C)C)C2)C[C@@H]1C>>CC(C)N1CCN(C(=O)[C@H]2CCNC2)C[C@@H]1C | null | C1COCCO1 | CO | Cl | null | train |
US20100298292A1 | C1=Cc2ccccc2CCC1.C1CCOC1.C[N+](=O)[O-].[Li]CCCC>>CN1C[C@@H]2CCCc3ccccc3[C@@H]2C1 | null | C1CCOC1 | O | CC(C)NC(C)C | null | train |
US04124596 | CC(C(=O)O)c1cccc(C(=O)c2cc3ccsc3s2)c1.CN(C)CCN>>CC(C(=O)NCCN(C)C)c1cccc(C(=O)c2cc3ccsc3s2)c1 | null | CCOCC | Cl | null | null | train |
US20070265272A1 | CNCCN(C)C.O=C(O)c1ccc(-c2cnc3nnn(Cc4ccc5ncccc5c4)c3n2)cc1>>CN(C)CCN(C)C(=O)c1ccc(-c2cnc3nnn(Cc4ccc5ncccc5c4)c3n2)cc1 | null | CN(C)C=O | null | CCN(CC)CC | CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F | train |
US20070112005A1 | Nc1ccccc1NC(=O)c1nc(C2CCC2)n2ccnc(N)c12>>Nc1nccn2c(C3CCC3)nc(-c3nc4ccccc4[nH]3)c12 | null | CC(=O)O | null | null | null | train |
US20070167443A1 | COC(=O)C(=CNc1cccnc1)C(=O)c1ccc(C)c(C)c1>>Cc1ccc(C(=O)c2c[nH]c3cccnc3c2=O)cc1C | null | c1ccc(Oc2ccccc2)cc1 | null | CCCCCC | null | train |
US20130210796A1 | CC(=O)OCc1nnnn1-c1cc(C(F)(F)F)c(C#N)cc1C>>Cc1cc(C#N)c(C(F)(F)F)cc1-n1nnnc1CO | null | C1CCOC1 | O | [Li+].[OH-] | null | train |
US20140094462A1 | CC(=O)OC(C)=O.N[C@@H]1CC=CCCCOC(=O)[C@@H]2CCCN2C1=O>>CC(=O)N[C@@H]1CC=CCCCOC(=O)[C@@H]2CCCN2C1=O | null | CN(C)C=O | null | CCN(CC)CC | null | train |
US05811439 | CI.O=C(O)c1cccc2c1ccn2CC(O)c1ccccc1>>COC(=O)c1cccc2c1ccn2CC(O)c1ccccc1 | null | CN(C)C=O | null | [Cl-].[NH4+] | O=C([O-])[O-].[K+].[K+] | train |
US20070173501A1 | CC1C(=O)COC1=O.O=C1Cc2ccc(F)cc2N1>>COC1=CC(=C2C(=O)Nc3cc(F)ccc32)OC1 | null | C1CCOC1 | null | C[Si](C)(C)[N-][Si](C)(C)C.[Li+] | null | train |
US20090088425A1 | CC(c1ccc(CO)cc1Cl)C(O)(c1ccnc(Cl)c1)C(F)(F)F.CS(=O)(=O)Cl>>CC(c1ccc(COS(C)(=O)=O)cc1Cl)C(O)(c1ccnc(Cl)c1)C(F)(F)F | null | C1CCOC1 | CCOC(C)=O | CCN(CC)CC | null | train |
US20140024690A1 | COc1cccc(-c2cc(CC[C@](C)(C(=O)O)S(C)(=O)=O)no2)c1F.NOC1CCCCO1>>COc1cccc(-c2cc(CC[C@](C)(C(=O)NOC3CCCCO3)S(C)(=O)=O)no2)c1F | CN(C)c1ccncc1 | CCOC(C)=O | O | CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 | CCN(C(C)C)C(C)C | train |
US05244863 | CC(=O)N=c1sc(C)cn1-c1cccc(C(F)(F)F)c1>>Cc1cn(-c2cccc(C(F)(F)F)c2)c(=N)s1 | null | CCO | O | Cl | null | train |
US20130116235A1 | IC1COC1.O=[N+]([O-])c1c[nH]cn1>>O=[N+]([O-])c1cn(C2COC2)cn1 | null | C1COCCO1 | null | O=C([O-])[O-].[Cs+].[Cs+] | null | train |
US05409927 | CC(C)[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](Cc1ccccc1)C(=O)O.[NH-]N1CCOCC1>>CC(C)[C@H](N)C(=O)N[C@@H](Cc1ccccc1)C(=O)O.[NH-]N1CCOCC1 | [Pd] | CO | null | null | null | train |
US20090298823A1 | CN1C(=O)CCc2cc(N)ccc21.Cc1ccc(S(=O)(=O)n2cc(-c3ccc(F)cc3)c3c(NC4CC4)nc(Cl)nc32)cc1>>CN1C(=O)CCc2cc(Nc3nc(N)c4c(-c5ccc(F)cc5)c[nH]c4n3)ccc21 | null | CCCCO | null | C[Si](C)(C)Cl | null | train |
US20140163002A1 | CN(C)C=O.Cc1ccc(Cl)c(F)c1>>Cc1ccc(Cl)c(F)c1C=O | null | C1CCOC1 | O | CC1(C)CCCC(C)(C)N1 | [Li]CCCC | train |
US20140336153A1 | Cc1c(C2(O)CCN(Cc3ccccc3)CC2)oc2ccccc12>>Cc1c(C2(O)CCNCC2)oc2ccccc12 | [Pd] | CO | null | null | null | train |
US20100286275A1 | CO.O=C(O)c1cccc(Br)c1>>COC(=O)c1cccc(Br)c1 | null | O=S(=O)(O)O | null | null | null | train |
US20100069383A1 | COc1ccc(N(C)c2nc(CC#N)nc3ccccc23)cc1>>COc1ccc(N(C)c2nc(CCN)nc3ccccc23)cc1 | [Pd] | CO | ClCCl | Cl | null | train |
US20110046171A1 | CCNC(=NS(=O)(=O)c1ccc2c(c1)NCC2)N1CC(CC)C=N1>>CCNC(=NS(=O)(=O)c1ccc2cc[nH]c2c1)N1CC(CC)C=N1 | null | Cc1ccccc1 | null | null | null | train |
US20050009838A1 | CC(C)(C)OC(=O)N1CCC(=O)CC1.CCCCc1cccs1>>CCCCc1ccc(C2(O)CCN(C(=O)OC(C)(C)C)CC2)s1 | null | C1CCOC1 | C1CCOC1 | [Li]CCCC | null | train |
US20150376130A1 | COC(=O)c1cccnc1F.Nc1ccccc1>>COC(=O)c1cccnc1Nc1ccccc1 | null | ClCCl | null | null | null | train |
US20080090813A1 | CC(C)(C)c1cccc(-c2cc(CCCO)nc(C#N)n2)c1>>CC(C)(C)c1cccc(-c2cc(CCC=O)nc(C#N)n2)c1 | null | CCOC(C)=O | ClCCl | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | null | train |
US05326755 | COS(=O)(=O)OC.O=C(O)C=Cc1ccc(Cl)c(Cl)c1>>COC(=O)C=Cc1ccc(Cl)c(Cl)c1 | null | CC(C)=O | null | O=C([O-])[O-].[K+].[K+] | null | train |
US20140243334A1 | COC(=O)C1CCc2ccc(Oc3cccc(N)c3)cc2C1.O=C(Cl)C1CC1>>COC(=O)C1CCc2ccc(Oc3cccc(NC(=O)C4CC4)c3)cc2C1 | null | ClCCl | null | CCN(CC)CC | Cl | train |
US20080021209A1 | C1COCCOCCOCCOCCO1.CC(=O)N(C)C.CCCCCCBr>>CCCCCCOCCCCCC.O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@H]12 | null | CC(=O)N(C)C | null | null | null | train |
US05929097 | BrCc1ccccc1CBr.COC(=O)c1cccc(O)c1NS(=O)(=O)c1ccc(OC)cc1>>COC(=O)c1cccc2c1N(S(=O)(=O)c1ccc(OC)cc1)Cc1ccccc1CO2 | null | CCOCC | CN(C)C=O | [H-].[Na+] | null | train |
US20100280068A1 | C#Cc1cnc2ccc(OC(SC)C(=O)NC(C)(C#C)CO)cc2c1>>C#Cc1cnc2ccc(OC(SC)C(=O)NC(C)(C#C)C=O)cc2c1 | null | ClCCl | null | CC(=O)OI1(OC(C)=O)(OC(C)=O)OC(=O)c2ccccc21 | O=S([O-])([O-])=S.[Na+].[Na+] | train |
US20030096826A1 | CC(=O)Nc1ccc(S(=O)(=O)N[C@H](C#N)CC(=O)OC(C)(C)C)c(OCCc2cccc3ncccc23)c1>>CC(=O)Nc1ccc(S(=O)(=O)N[C@H](C#N)CC(=O)O)c(OCCc2cccc3ncccc23)c1 | null | ClCCl | O=C(O)C(F)(F)F | null | null | train |
US06093732 | CSCC#Cc1cc(F)c2ncc(C(=O)NCc3ccc(Cl)cc3)c(O)c2c1>>CSCCCc1cc(F)c2ncc(C(=O)NCc3ccc(Cl)cc3)c(O)c2c1 | [Pd] | CO | ClCCl | null | null | train |
US20130150339A1 | COc1cc2c(Cl)ccnc2cc1S(=O)(=O)Cl.COc1ccc(CNc2nccs2)cc1>>COc1ccc(CN(c2nccs2)S(=O)(=O)c2cc3nccc(Cl)c3cc2OC)cc1 | null | C1CCOC1 | null | [Cl-].[NH4+] | C[Si](C)(C)[N-][Si](C)(C)C.[Li+] | train |
US05308857 | BrBr.CC(=O)NC(=O)NCc1ccc(C(C)=O)o1>>CC(=O)NC(=O)NCc1ccc(C(=O)CBr)o1 | null | ClCCl | null | null | null | train |
US04237275 | CC(C)C=C1C=C(CN)C=CN1>>CC(C)CN=Cc1ccncc1 | null | Cc1ccccc1 | null | CC(C)(C)[O-].[K+] | null | train |
US20010007903A1 | CS(=O)(=O)Cl.Cc1nnsc1CO>>Cc1nnsc1COS(C)(=O)=O | null | ClCCl | null | CCN(CC)CC | O | train |
US20030203954A1 | CCOC(=O)Cn1nc(-c2ccccc2O)nc1-c1ccccc1O.NCCN(CCO)CCO>>O=C(Cn1nc(-c2ccccc2O)nc1-c1ccccc1O)NCCN(CCO)CCO | null | CCO | null | null | null | train |
US20090247519A1 | BrBr.COc1ccc(OC(C)=O)cc1>>COc1ccc(OC(C)=O)cc1Br | null | CC(=O)O | O | CC(=O)[O-].[Na+] | null | train |
US06451804B1 | C[Si](C)(C)CCOCN1C(=O)N(c2ccccc2Cl)Cc2cnc(N[C@@H]3CC[C@@H](NS(C)(=O)=O)CC3)nc21>>CS(=O)(=O)N[C@@H]1CC[C@@H](Nc2ncc3c(n2)NC(=O)N(c2ccccc2Cl)C3)CC1 | null | CO | null | Cl | null | train |
US20120252801A1 | CCN1CC(C)(C)OC(=O)C1CC(=O)O.NCc1ccccc1>>CCN1CC(C)(C)OC(=O)C1CC(=O)NCc1ccccc1 | 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 |
US20130303533A1 | CCI.Fc1ccc(Sc2nc(Cl)c3cc[nH]c3n2)cc1>>CCn1ccc2c(Cl)nc(Sc3ccc(F)cc3)nc21 | null | CN(C)C=O | null | [H-].[Na+] | null | train |
US20120269724A1 | CC(C)(C)Oc1ccccc1CN(CCCCl)Cc1ccccn1.c1ccc(C2CCNCC2)cc1>>CC(C)(C)Oc1ccccc1CN(CCCN1CCC(c2ccccc2)CC1)Cc1ccccn1 | null | CC#N | null | O=C([O-])[O-].[K+].[K+] | null | train |
US20080177108A1 | COc1ccc(O)c(C=O)c1.CS(=O)(=O)OCCOS(C)(=O)=O>>COc1ccc(OCCOS(C)(=O)=O)c(C=O)c1 | null | CN(C)C=O | null | O=C([O-])[O-].[Cs+].[Cs+] | null | train |
US20040224958A1 | CCNc1nc(Nc2ccccc2)ncc1C=CC(=O)OCC>>CCn1c(=O)ccc2cnc(Nc3ccccc3)nc21 | null | CCN(CC)CC | null | C1CCC2=NCCCN2CC1 | null | train |
US20040023974A1 | COC(=O)Cc1ccccc1N(CC(=O)OC(C)(C)C)S(=O)(=O)NC(=O)OC(C)(C)C>>COC(=O)Cc1ccccc1N(CC(=O)O)S(N)(=O)=O | null | ClCCl | O=C(O)C(F)(F)F | null | null | train |
US20110269734A1 | Cc1nc(OCCCC2CCNCC2)ccc1C(=O)NC(CO)CO.Clc1cnc(Cl)nc1>>Cc1nc(OCCCC2CCN(c3ncc(Cl)cn3)CC2)ccc1C(=O)NC(CO)CO | null | CCOC(C)=O | CS(C)=O | C1CCC2=NCCCN2CC1 | Cl | train |
US20150299121A1 | Cc1c(CN2CCN(C(=O)OC(C)(C)C)[C@@H](C)C2)cc(F)cc1NC(=O)c1cccc(C#N)c1>>Cc1c(CN2CCN[C@@H](C)C2)cc(F)cc1NC(=O)c1cccc(C#N)c1 | null | ClCCl | null | O=C(O)C(F)(F)F | null | train |
US20020040048A1 | COc1ccc(CS[C@@H]2C[C@@H](C(=O)N(C)NC(=O)OC(C)(C)C)N(S(=O)(=O)c3ccc4ccccc4c3)C2)cc1>>COc1ccc(CS[C@@H]2C[C@@H](C(=O)N(C)N)N(S(=O)(=O)c3ccc4ccccc4c3)C2)cc1 | null | ClCCl | null | O=C(O)C(F)(F)F | null | train |
US20050070541A1 | CCCOc1ccc(S(=O)(=O)Cl)cc1-c1nn2c(CCC)nc(C)c2c(=O)[nH]1.OC1CCNCC1>>CCCOc1ccc(S(=O)(=O)N2CCC(O)CC2)cc1-c1nn2c(CCC)nc(C)c2c(=O)[nH]1 | null | CO | ClCCl | null | null | train |
US20140275080A1 | C=C(C)OC(=O)Cl.NC(=O)CCCOC(F)(F)F>>C=C(C)OC(=O)NC(=O)CCCOC(F)(F)F | null | C1CCOC1 | null | C[Si](C)(C)[N-][Si](C)(C)C.[Li+] | null | train |
US05143920 | CCCC(=O)c1cnc2c(C(C)=O)cccc2c1Cl.Cc1cc(O)ccc1N>>CCCC(=O)c1cnc2c(C(C)=O)cccc2c1Nc1ccc(O)cc1C | null | C1COCCO1 | null | null | null | train |
US06133287 | CN1CC=C(c2c[nH]c3c(F)cc(F)cc23)CC1.Cc1cc(C)c(S(=O)(=O)Cl)c(C)c1>>Cc1cc(C)c(S(=O)(=O)n2cc(C3=CCN(C)CC3)c3cc(F)cc(F)c32)c(C)c1 | null | C1CCOC1 | null | C[Si](C)(C)[N-][Si](C)(C)C.[Na+] | null | train |
US20120270865A2 | CCOC(=O)CCN(C)C(=O)c1ccc(NC(c2oc3ccc(C#N)cc3c2C)C2CCCCC2)cc1>>Cc1c(C(Nc2ccc(C(=O)N(C)CCC(=O)O)cc2)C2CCCCC2)oc2ccc(C#N)cc12 | null | CCO | null | C1CCOC1 | [Li+].[OH-] | train |
US20140179733A1 | CC(C)c1c(N)cnn1-c1ccc(F)cc1.CCC(C(=O)O)n1cc(C(F)(F)F)nc1C>>CCC(C(=O)Nc1cnn(-c2ccc(F)cc2)c1C(C)C)n1cc(C(F)(F)F)nc1C | null | CN(C)C=O | O | CCN(C(C)C)C(C)C | CN(C)C(On1nnc2cccnc21)=[N+](C)C.F[P-](F)(F)(F)(F)F | train |
US20080261918A1 | COc1nc(NCCNCc2ccccc2)nc(OC)c1NC(=O)c1ccc(Oc2cc([Si](C)(C)C)ccc2C)o1>>COc1nc(NCCN)nc(OC)c1NC(=O)c1ccc(Oc2cc([Si](C)(C)C)ccc2C)o1 | [Pd] | CCO | null | null | null | train |
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