Chlorine → HCID 178427205, compound

HRID 2053879Notes

Reaction equation

HRID 2053879 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.[C:49]([O:53][C:54]([CH2:56][O:57][CH2:58][C@H:59]([NH2:70])[C:60]1[NH:64][C:63]2[CH:65]=[CH:66][C:67]([Cl:69])=[CH:68][C:62]=2[N:61]=1)=[O:55])([CH3:52])([CH3:51])[CH3:50].ClCl>O1CCCC1.ClCCl.CO>[C:49]([O:53][C:54]([CH2:56][O:57][CH2:58][C@H:59]([NH:70][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:60]1[NH:64][C:63]2[CH:65]=[CH:66][C:67]([Cl:69])=[CH:68][C:62]=2[N:61]=1)=[O:55])([CH3:52])([CH3:50])[CH3:51]

Participants

8

Reactant 5

HCID 24526Chlorine2×HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 178451359HCID 178451359, compound

Product 1

HCID 178427205HCID 178427205, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and (R)-2-(C-tert-butoxycarbonylmethyloxy)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine in tetrahydrofuran. Yield: 82%; Rf value: 0.70 (silica gel; dichloromethane/methanol=95:5); C28H33ClN4O5 (541.05); mass spectrum: (M+H)+=541/543 (chlorine isotope) and (M−H)−=539/541 (chlorine isotope).

Sources & evidence

ORD record
ord-40ec86a2c3b249b5b8a8129f4b4c5bd2
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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