Trifluoroacetic acid → HCID 178427174, compound

HRID 2053935Notes

Reaction equation

HRID 2053935 reaction equation
C(OC(N1C2C=CC(Cl)=CC=2N=[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]([OH:23])=O)=O)(C)(C)C.CN(C(O[N:49]1N=[N:56][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][C:50]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[C:72]([O:76][C:77]([NH:79][CH2:80][C@H:81]1[CH2:85][CH2:84][CH2:83][NH:82]1)=[O:78])([CH3:75])([CH3:74])[CH3:73].FC(F)(F)C(O)=O.[Cl:93]Cl>C(#N)C.C(OCC)(=O)C.C(O)C>[Cl:93][C:54]1[CH:53]=[CH:52][C:51]2[NH:56][C:9]([C@@H: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:82]3[CH2:83][CH2:84][CH2:85][C@@H:81]3[CH2:80][NH:79][C:77]([O:76][C:72]([CH3:75])([CH3:73])[CH3:74])=[O:78])=[O:23])=[N:49][C:50]=2[CH:55]=1

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22883086tert-Butyl {[(2R)-pyrrolidin-2-yl]methyl}carbamateHCID 69309776HCID 69309776, compound

Product 1

HCID 178427174HCID 178427174, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21584252Ethanol ethylacetateSolvent

Procedure

Prepared analogously to Example 1g from N-[1-(1-tert-butoxycarbonyl-5-chloro-1H-benzimidazol-2-yl)-3-hydroxycarbonylpropyl]-3-methyl-4-(pyrrolidin 1-ylcarbonyl)benzamide, TBTU, diisopropylethylamine, (R)-2-tert-butoxycarbonylaminomethylpyrrolidine in acetonitrile, and subsequent reaction with trifluoroacetic acid analogously to Example 17. Yield: 51%; Rf value: 0.59 (silica gel; ethyl acetate/ethanol=7:3); C34H43ClN6O5 (651.20); mass spectrum: (M+H)+=651/653 (chlorine isotope).

Sources & evidence

ORD record
ord-e99fc1298474457a9e6853e8f312b4ab
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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