Ammonia → HCID 178427015, compound

HRID 2053813Notes

Reaction equation

HRID 2053813 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][CH2:59][CH2:58][CH2:57]1)=[O:55])[C:48](O)=[O:49].N.BrBr>O1CCCC1.ClCCl.C(O)C>[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][CH2:58][CH2:59][CH2:60]4)=[O:55])=[C:45]([CH3:44])[CH:46]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

9

Reactant 6

HCID 222AmmoniaHCID 24408BromineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 178510547HCID 178510547, compound

Product 1

HCID 178427015HCID 178427015, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584144Dichloromethane ethanolSolvent

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-(pyrrolidin-1-ylcarbonyl)benzoic acid in tetrahydrofuran. Yield: 190 mg (76%); Rf value: 0.67 (silica gel; dichloromethane/ethanol=8:2+2% ammonia solution); C20H20BrN5O2 (442,32); mass spectrum: (M+H)+=442/444 (bromine isotope).

Sources & evidence

ORD record
ord-3a185bdfd7ef48c1aa305769ae712b11
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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