Sodium Iodide → 8-(2-tert-Butoxycarbonylamino-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine

HRID 1955007Notes

Reaction equation

HRID 1955007 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:13]([O:17][C:18]([NH:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:22]=1[CH2:23]Cl)=[O:19])([CH3:16])([CH3:15])[CH3:14].[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[C:13]([O:17][C:18]([NH:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:22]=1[CH2:23][NH:1][C:2]1[C:3]2[N:4]([C:8]([CH3:12])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 143684822-Tert-butoxycarbonylamino-6-methylbenzylchlorideHCID 218739802,3-Dimethylimidazo[1,2-a]pyridin-8-amine

Product 1

HCID 232872978-(2-tert-Butoxycarbonylamino-6-methylbenzylamino)-2,3-dimethylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Starting from 8-amino-2,3-dimethylimidazo[1,2-a]pyridine (4.8 g), 2-tert-butoxycarbonylamino-6-methylbenzyl chloride (9.2 g), sodium iodide (5.5 g) and sodium carbonate (8.0 g) in acetone (250 ml) analogously using the process of Example B1 gives, after chromatography on silica gel (eluent toluene/dioxane 20:1) and recrystallization from diisopropyl ether, 7.1 g (62%) of the title compound of m.p. 149-152° C.

Workup

  1. customgives
  2. customafter chromatography on silica gel (eluent toluene/dioxane 20:1) and recrystallization from diisopropyl ether, 7.1 g (62%) of the title compound of m.p. 149-152° C.

Sources & evidence

ORD record
ord-33d577e1133040fcb3f47ece4ad2dbaf
Source dataset
uspto-grants-2000_09
Patent number
US06124313

Reaction notes

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