Trifluoroacetic acid → HCID 178464216, compound

HRID 2053865Notes

Reaction equation

HRID 2053865 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:11]=2[N:10]=[C:9]1[CH:18]([NH:24][C:25](=[O:40])[C:26]1[CH:31]=[CH:30][C:29]([C:32]([N:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)=[O:33])=[C:28]([CH3:39])[CH:27]=1)[CH2:19][CH2:20][C:21](O)=[O:22])=O)(C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH:63]([N:66](C(C)C)[CH2:67][CH3:68])(C)[CH3:64].C(NCC)C.FC(F)(F)C(O)=O.ClCl>O1CCCC1.C(OCC)(=O)C.C(O)C>[Cl:17][C:15]1[CH:14]=[CH:13][C:12]2[NH:8][C:9]([CH:18]([NH:24][C:25](=[O:40])[C:26]3[CH:31]=[CH:30][C:29]([C:32]([N:34]4[CH2:35][CH2:36][CH2:37][CH2:38]4)=[O:33])=[C:28]([CH3:39])[CH:27]=3)[CH2:19][CH2:20][C:21]([N:66]([CH2:67][CH3:68])[CH2:63][CH3:64])=[O:22])=[N:10][C:11]=2[CH:16]=1

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 8021DiethylamineHCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69309776HCID 69309776, compound

Product 1

HCID 178464216HCID 178464216, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584252Ethanol ethylacetateSolvent

Procedure

Prepared analogously to Example 1g from N-[1-(1-tert-butoxycarbonyl-5-chlorobenzimidazol-2-yl)-3-hydroxycarbonylpropyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide, TBTU, diisopropylethylamine, and diethylamine in tetrahydrofuran followed by treatment analogously to Example 17 with trifluoroacetic acid. Yield: 76%; Rf value: 0.16 (silica gel; ethyl acetate/ethanol=9:1); C28H34ClN5O3 (524.06); mass spectrum: (M+H)+=524/526 (chlorine isotope).

Sources & evidence

ORD record
ord-1b6f82a89acf4c3cad6dbe087b01432d
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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