Chlorine → HCID 178503802, compound

HRID 2054032Notes

Reaction equation

HRID 2054032 reaction equation
[N:1]1([C:6]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][C:9]=2[CH3:17])=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[Cl:49][C:50]1[CH:63]=[CH:62][C:53]2[NH:54][C:55]([C@@H:57]([NH2:61])[CH2:58][S:59][CH3:60])=[N:56][C:52]=2[CH:51]=1.ClCl>O1CCCC1.ClCCl.C(O)C>[Cl:49][C:50]1[CH:63]=[CH:62][C:53]2[NH:54][C:55]([C@@H:57]([NH:61][C:12](=[O:14])[C:11]3[CH:15]=[CH:16][C:8]([C:6]([N:1]4[CH2:2][CH:3]=[CH:4][CH2:5]4)=[O:7])=[C:9]([CH3:17])[CH:10]=3)[CH2:58][S:59][CH3:60])=[N:56][C:52]=2[CH:51]=1

Participants

8

Reactant 5

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118586383-Methyl-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzoic acidHCID 178503800HCID 178503800, compound

Product 1

HCID 178503802HCID 178503802, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 4-(2,5-dihydropyrrol-1-ylcarbonyl)-3-methylbenzoic acid, TBTU, diisopropylethylamine, and (1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methylsulfanylethylamine in tetrahydrofuran. Yield: 43%; Rf value: 0.47 (silica gel: dichloromethane/ethanol=9:1); C23H23ClN4O2S (454.98); mass spectrum: (M+H)+=455/457 (chlorine isotope).

Sources & evidence

ORD record
ord-147d66921ee5449eadca04d014c1a5f7
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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