Chlorine → HCID 59655047, compound

HRID 2053915Notes

Reaction equation

HRID 2053915 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[N:55]=[C:54]2[N:56]=[C:57]([CH:59]([NH2:61])[CH3:60])[NH:58][C:53]2=[CH:52][CH:51]=1.ClCl>CN(C)C=O.ClCCl.C(O)C>[Cl:49][C:50]1[N:55]=[C:54]2[N:56]=[C:57]([CH:59]([NH:61][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][C:10]([C:11]([N:13]4[CH2:17][CH2:16][CH2:15][CH2:14]4)=[O:12])=[C:2]([CH3:1])[CH:3]=3)[CH3:60])[NH:58][C:53]2=[CH:52][CH:51]=1

Participants

8

Reactant 5

HCID 24526ChlorineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 86620551HCID 86620551, compound

Product 1

HCID 59655047HCID 59655047, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Prepared analogously to Example 1g from 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, TBTU, diisopropylethylamine, and 1-(5-chloro-1H-imidazo[4,5-b]pyridin-2-yl)ethylamine in dimethylformamide. Yield: 42%; Rf value: 0.45 (silica gel; dichloromethane/ethanol=9:1); C21H22ClN5O2 (411.89); mass spectrum: (M+H)+=410/412 (chlorine isotope).

Sources & evidence

ORD record
ord-37e8a3ab45274eee90fed5a99a438d37
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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