Chlorine → Rac.-n-[1-(5-chloro-1h-indol-2-yl)ethyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamide

HRID 2054058Notes

Reaction equation

HRID 2054058 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][CH2:16][CH2:15][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.[Cl:49][C:50]1[CH:51]=[C:52]2[C:56](=[CH:57][CH:58]=1)[NH:55][C:54]([CH:59]([NH2:61])[CH3:60])=[CH:53]2.ClCCl.C(O)C.N.ClCl>O1CCCC1>[Cl:49][C:50]1[CH:51]=[C:52]2[C:56](=[CH:57][CH:58]=1)[NH:55][C:54]([CH:59]([NH:61][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([C:11]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[O:12])=[C:2]([CH3:1])[CH:3]=1)[CH3:60])=[CH:53]2

Participants

8

Reactant 6

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 22609213HCID 22609213, compoundHCID 653341651-(5-Chloro-1h-indol-2-yl)ethan-1-amine

Product 1

HCID 59655324Rac.-n-[1-(5-chloro-1h-indol-2-yl)ethyl]-3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzamideYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and rac.-1-(5-chloro-1H-indol-2-yl)ethylamine in tetrahydrofuran. Yield: 95%; Rf value: 0.65 (silica gel: dichloromethane/ethanol/ammonia=9:1:0.1); C23H24ClN3O2 (409.915); mass spectrum: (M+H)+=410/412 (chlorine isotope).

Sources & evidence

ORD record
ord-cbdac1b4b729441b84fb097bcfda02d9
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

Loading…