Chlorine → HCID 178427082, compound

HRID 2053860Notes

Reaction equation

HRID 2053860 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12])[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH2:49]([O:56][C:57]([CH2:59][CH2:60][CH:61]([NH2:72])[C:62]1[NH:66][C:65]2[CH:67]=[CH:68][C:69]([Cl:71])=[CH:70][C:64]=2[N:63]=1)=[O:58])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.ClCl>O1CCCC1.C(OCC)(=O)C.C(O)C>[CH2:49]([O:56][C:57]([CH2:59][CH2:60][CH:61]([NH:72][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])=[C:2]([CH3:1])[CH:3]=1)[C:62]1[NH:66][C:65]2[CH:67]=[CH:68][C:69]([Cl:71])=[CH:70][C:64]=2[N:63]=1)=[O:58])[C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1

Participants

8

Reactant 5

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 178511063HCID 178511063, compound

Product 1

HCID 178427082HCID 178427082, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584252Ethanol ethylacetateSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and 3-benzyloxycarbonyl-1-(5-chloro-1H-benzimidazol-2-yl)propylamine in tetrahydrofuran. Yield: 70%; Rf value: 0.24 (silica gel; ethyl acetate/ethanol=95:5); C31H31ClN4O4 (559.06); mass spectrum: (M+H)+=559/561 (chlorine isotope).

Sources & evidence

ORD record
ord-a18d1770b5e2467487d35be97ccb00b0
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

Loading…