Chlorine → HCID 178427127, compound

HRID 2054045Notes

Reaction equation

HRID 2054045 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][CH:16]=[CH: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@@H:54]([CH3:67])[C@H:55]([NH2:66])[C:56]1[NH:60][C:59]2[CH:61]=[CH:62][C:63]([Cl:65])=[CH:64][C:58]=2[N:57]=1)([CH3:52])([CH3:51])[CH3:50].ClCl>O1CCCC1.ClCCl.C(O)C>[C:49]([O:53][C@@H:54]([CH3:67])[C@H:55]([NH:66][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([C:11]([N:13]2[CH2:17][CH:16]=[CH:15][CH2:14]2)=[O:12])=[C:2]([CH3:1])[CH:3]=1)[C:56]1[NH:60][C:59]2[CH:61]=[CH:62][C:63]([Cl:65])=[CH:64][C:58]=2[N:57]=1)([CH3:52])([CH3:50])[CH3:51]

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 178462271HCID 178462271, compound

Product 1

HCID 178427127HCID 178427127, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and (1R,2S)-2-tert-butoxy-1-(5-chloro-1H-benzimidazol-2-yl)propylamine in tetrahydrofuran. Yield: 86%; Rf value: 0.61 (silica gel: dichloromethane/ethanol=9:1); C27H31ClN4O3 (495.02); mass spectrum: (M+H)+=495/497 (chlorine isotope).

Sources & evidence

ORD record
ord-bf29faa1ccf54d52905d946d7c6981d1
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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