Chlorine → HCID 178427137, compound

HRID 2054048Notes

Reaction equation

HRID 2054048 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][C:10]=1[CH3:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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:50][C:51]1[CH:62]=[CH:61][C:54]2[NH:55][C:56]([C@@H:58]([NH2:60])[CH3:59])=[N:57][C:53]=2[CH:52]=1.ClCl>O1CCCC1.ClCCl.C(O)C>[C:1]([C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH:60][C@H:58]([C:56]2[NH:55][C:54]3[CH:61]=[CH:62][C:51]([Cl:50])=[CH:52][C:53]=3[N:57]=2)[CH3:59])=[O:15])=[CH:11][C:10]=1[CH3:18])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 24526Chlorine2×HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 42034613(S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamineHCID 57346846HCID 57346846, compound

Product 1

HCID 178427137HCID 178427137, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 4-benzoyl-3-methylbenzoic acid, TBTU, diisopropylethylamine, and (1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine in tetrahydrofuran. Yield: 91%; Rf value: 0.54 (silica gel: dichloromethane/ethanol=9:1); C24H20ClN3O2 (417.894); mass spectrum: (M+H)+=418/420 (chlorine isotope) and (M−H)−=416/418 (chlorine isotope).

Sources & evidence

ORD record
ord-26395ac0f3a14b6989614eb4796e4b61
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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