Chlorine → HCID 178427112, compound

HRID 2053849Notes

Reaction equation

HRID 2053849 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.[OH:49][CH2:50][CH:51]([NH2:62])[C:52]1[NH:56][C:55]2[CH:57]=[CH:58][C:59]([Cl:61])=[CH:60][C:54]=2[N:53]=1.ClCl>O1CCCC1.ClCCl.C(O)C>[Cl:61][C:59]1[CH:58]=[CH:57][C:55]2[NH:56][C:52]([CH:51]([NH:62][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][C:10]([C:11]([N:13]4[CH2:17][CH2:16][CH2:15][CH2:14]4)=[O:12])=[C:2]([CH3:1])[CH:3]=3)[CH2:50][OH:49])=[N:53][C:54]=2[CH:60]=1

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 178511393HCID 178511393, compound

Product 1

HCID 178427112HCID 178427112, compoundYield 68%

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 2-hydroxy-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine in tetrahydrofuran. Yield: 68%; Rf value: 0.40 (silica gel; dichloromethane/ethanol=95:5); C22H23ClN4O3 (426.90); mass spectrum: (M+H)+=427/429 (chlorine isotope) and (M−H)-=425/427 (chlorine isotope).

Sources & evidence

ORD record
ord-2c5f520f49dc4d57b7aff744bd7aeac6
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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