Trifluoroacetic acid → HCID 178427170, compound

HRID 2053933Notes

Reaction equation

HRID 2053933 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]([OH:23])=O)=O)(C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH3:72][N:73]1[CH2:76][C:75]2([CH2:80][CH2:79][NH:78][CH2:77]2)[CH2:74]1.FC(F)(F)C(O)=O.ClCl>C(#N)C.C(OCC)(=O)C.C(O)C.C(N(CC)CC)C>[Cl:17][C:15]1[CH:14]=[CH:13][C:12]2[NH:8][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:78]3[CH2:79][CH2:80][C:75]4([CH2:76][N:73]([CH3:72])[CH2:74]4)[CH2:77]3)=[O:23])=[N:10][C:11]=2[CH:16]=1

Participants

9

Reactant 6

HCID 6422Trifluoroacetic acidHCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 151074502,6-Diazaspiro[3.4]octane, 2-methyl-HCID 69309776HCID 69309776, compound

Product 1

HCID 178427170HCID 178427170, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 22328969EtOH ethyl acetate triethylamineSolvent

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, 2-methyl-2,6-diazaspiro[3.4]octane in acetonitrile, and subsequent reaction with trifluoroacetic acid analogously to Example 17. Yield: 67%; Rf value: 0.05 (silica gel; ethyl acetate/ethanol/triethylamine=70:27:3); C31H37ClN6O3 (577.13); mass spectrum: (M+H)+=577/579 (chlorine isotope).

Sources & evidence

ORD record
ord-e66118029e064cc0a221a5b2f7f0b4e6
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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