Chlorine → HCID 178462086, compound

HRID 2054052Notes

Reaction equation

HRID 2054052 reaction equation
[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[N:6]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=3)[CH:5]=[CH:4][C:3]1=2.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:51][C:52]1[CH:63]=[CH:62][C:55]2[NH:56][C:57]([C@@H:59]([NH2:61])[CH3:60])=[N:58][C:54]=2[CH:53]=1.[Cl:64]Cl>O1CCCC1.C(OCC)(=O)C>[Cl:64][C:19]1[CH:18]=[C:14]([CH:13]=[CH:12][C:11]=1[N:6]1[C:7]2[CH2:8][CH2:9][CH2:10][C:2](=[O:1])[C:3]=2[CH:4]=[CH:5]1)[C:15]([NH:61][C@H:59]([C:57]1[NH:56][C:55]2[CH:62]=[CH:63][C:52]([Cl:51])=[CH:53][C:54]=2[N:58]=1)[CH3:60])=[O:17]

Participants

8

Reactant 5

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 42034613(S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamineHCID 69312715HCID 69312715, compound

Product 1

HCID 178462086HCID 178462086, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Prepared analogously to Example 1g from 4-(4-oxo-4,5,6,7-tetrahydroindol-1-yl)benzoic acid, TBTU, diisopropylethylamine, and (1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine in tetrahydrofuran. Yield: 54%; Rf value: 0.41 (silica gel: ethyl acetate); C24H20Cl2N4O2 (467.354); mass spectrum: (M+H)+=467/469/471 (chlorine isotope).

Sources & evidence

ORD record
ord-94106d30cd094627b1f5196d00037d73
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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