4-(2-(4-amino-3-nitrophenyl)imidazo[1,2-a]pyridin-3-yl)-N-(3-(2-(dimethylamino)ethyl)phenyl)pyrimidin-2-amine → 4-(3-(2-(3-(2-(Dimethylamino)ethyl)phenylamino)pyrimidin-4-yl)imidazo[1,2-a]pyridin-2-yl)benzene-1,2-diamine

HRID 42265Notes

Reaction equation

HRID 42265 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][N:11]3[C:16]=2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])[CH:25]=3)[N:18]=2)=[CH:4][C:3]=1[N+:35]([O-])=O>[Pd].O1CCCC1>[CH3:34][N:32]([CH3:33])[CH2:31][CH2:30][C:26]1[CH:25]=[C:24]([NH:23][C:19]2[N:18]=[C:17]([C:16]3[N:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]4=[N:9][C:8]=3[C:5]3[CH:4]=[C:3]([NH2:35])[C:2]([NH2:1])=[CH:7][CH:6]=3)[CH:22]=[CH:21][N:20]=2)[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 1

HCID 687634124-(2-(4-amino-3-nitrophenyl)imidazo[1,2-a]pyridin-3-yl)-N-(3-(2-(dimethylamino)ethyl)phenyl)pyrimidin-2-amine

Product 1

HCID 687775604-(3-(2-(3-(2-(Dimethylamino)ethyl)phenylamino)pyrimidin-4-yl)imidazo[1,2-a]pyridin-2-yl)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 50 mL pressure bottle was charged with 4-(2-(4-amino-3-nitrophenyl)imidazo[1,2-a]pyridin-3-yl)-N-(3-(2-(dimethylamino)ethyl)phenyl)pyrimidin-2-amine (60 mg, 0.121 mmol) from EXAMPLE 10A and tetrahydrofuran (20 mL). The solution was treated with 50% palladium on carbon (30.0 mg, 0.282 mmol) and stirred for 24 hours at 30 psi at ambient temperature. The mixture was filtered through a nylon membrane and solvents were concentrated to provide the title compound. MS (ESI+) m/e 465.1 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane and solvents
  2. concentrationwere concentrated

Sources & evidence

ORD record
ord-9984c7a6caa64959896cca8499c9153c
Source dataset
uspto-grants-2013_09
Patent number
US08536180B2

Reaction notes

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