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

HRID 1377478Notes

Reaction equation

HRID 1377478 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

The title compound is prepared according to the procedure described for example 1 starting from 8-amino-2,3-dimethylimidazo[1,2-a]pyridine (4.8 g), 2-tert-butoxycarbonylamino-6-methylbenzylchloride (9.2 g), sodium iodide (5.5 g) and sodium carbonate (8.0 g) in acetone (250 ml). Purification by chromatography on silica gel (toluene/dioxane 20:1 as eluent) and crystallization from diisopropyl ether yield 7.1 g (62%) of m.p. 149°-152° C.

Workup

  1. customPurification by chromatography
  2. customon silica gel (toluene/dioxane 20:1 as eluent) and crystallization from diisopropyl ether yield 7.1 g (62%) of m.p. 149°-152° C.

Sources & evidence

ORD record
ord-6b041329237442c88929f711d8377873
Source dataset
uspto-grants-1997_09
Patent number
US05665730

Reaction notes

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