Diisopropylethylamine → HCID 178427014, compound

HRID 2053814Notes

Reaction equation

HRID 2053814 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][NH2:12])[NH:8][C:5]2=[N:6][CH:7]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH3:44][C:45]1[CH:46]=[C:47]([CH:51]=[CH:52][C:53]=1[C:54]([N:56]1[CH2:60][CH:59]=[CH:58][CH2:57]1)=[O:55])[C:48](O)=[O:49]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][NH:12][C:48](=[O:49])[C:47]3[CH:51]=[CH:52][C:53]([C:54]([N:56]4[CH2:57][CH:58]=[CH:59][CH2:60]4)=[O:55])=[C:45]([CH3:44])[CH:46]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 118586383-Methyl-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzoic acidHCID 178510547HCID 178510547, compound

Product 1

HCID 178427014HCID 178427014, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 1g from C-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)methylamine, TBTU, diisopropylethylamine, and 3-methyl-4-(2,5-dihydropyrrol-1-ylcarbonyl)benzoic acid in tetrahydrofuran. Purification is effected by chromatography on silica gel (gradient: dichloromethane/ethanol=100:0□80:20). Yield: 240 mg (96%); Rf value: 0.68 (silica gel; dichloromethane/ethanol=8:2+2% ammonia solution); C20H18BrN5O2 (440.30); mass spectrum: (M+H)+=440/442 (bromine isotope).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-69573e27b8ef478bae2072e1ce77308c
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

Loading…