Chlorine → HCID 178475122, compound

HRID 2054080Notes

Reaction equation

HRID 2054080 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]([NH:52][CH2:53][S:54][CH2:55][C@H:56]([NH2:67])[C:57]1[NH:61][C:60]2[CH:62]=[CH:63][C:64]([Cl:66])=[CH:65][C:59]=2[N:58]=1)(=[O:51])[CH3:50].ClCl>O1CCCC1.ClCCl.C(O)C>[C:49]([NH:52][CH2:53][S:54][CH2:55][C@H:56]([NH:67][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:57]1[NH:61][C:60]2[CH:62]=[CH:63][C:64]([Cl:66])=[CH:65][C:59]=2[N:58]=1)(=[O:51])[CH3:50]

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 178475121HCID 178475121, compound

Product 1

HCID 178475122HCID 178475122, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and (1R)-2-(acetylaminomethylsulfanyl)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine in tetrahydrofuran. Yield: 89%; Rf value: 0.40 (silica gel: dichloromethane/ethanol=9:1; C25H28ClN5O3S (514.05); mass spectrum: (M+H)+=514/516 (chlorine isotope).

Sources & evidence

ORD record
ord-34662dde34714ef09806891b404eb4f7
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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