Chlorine → 3-chloro-N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethyl]-4-(4,5,6,7-tetrahydroindol-1-yl)benzamide

HRID 2054056Notes

Reaction equation

HRID 2054056 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[CH:13]=[CH:12]1)[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.[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.ClCCl.C(O)C.N.ClCl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[CH:13]=[CH:12]1)[C:5]([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:7]

Participants

8

Reactant 6

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22609213HCID 22609213, compoundHCID 42034613(S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamineHCID 693152703-Chloro-4-(4,5,6,7-tetrahydroindol-1-yl)benzoic acid

Product 1

HCID 1784620853-chloro-N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethyl]-4-(4,5,6,7-tetrahydroindol-1-yl)benzamideYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 1g from 3-chloro-4-(4,5,6,7-tetrahydroindol-1-yl)benzoic acid, TBTU, diisopropylethylamine, and (1S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine in tetrahydrofuran. Yield: 25%; Rf value: 0.90 (silica gel: dichloromethane/ethanol/ammonia=4:1:0.1); C24H22C12N4O (453.371); mass spectrum: (M+H)+=453/455/457 (chlorine isotope).

Sources & evidence

ORD record
ord-b81cc26f6e4c49a0b6d8e6a6df630c4a
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

Loading…