Dimethylformamide → HCID 19876062, compound

HRID 1886457Notes

Reaction equation

HRID 1886457 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][N:11]3[C:15]4=[N:16][C:17]([CH3:21])=[CH:18][C:19]([CH3:20])=[C:14]4[N:13]=[C:12]3[CH2:22][CH3:23])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[C:26]12[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=1)NC(=O)O[C:27]2=[O:28].C[N:39]([CH:41]=[O:42])C>>[C:41]([C:36]1[CH:35]=[CH:34][CH:33]=[CH:32][C:26]=1[C:27]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][N:11]3[C:15]4=[N:16][C:17]([CH3:21])=[CH:18][C:19]([CH3:20])=[C:14]4[N:13]=[C:12]3[CH2:22][CH3:23])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)=[O:28])(=[O:42])[NH2:39]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8359Isatoic AnhydrideHCID 24758Sodium hydrideHCID 100407273-(5-indolyl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 19876062HCID 19876062, compoundYield 77%

Procedure

To a solution of the product of Example 2, Step A (200 mg, 0.66 mmol) in 7 mL of DMF was added NaH (53 mg, 1.23 mmol) and the mixture stirred for a few minutes. Isatoic anhydride (160 mg, 0.99 mmol) was added to the reaction mixture and it was stirred for 16 hours. The solvent was removed in vacuo and the resultant residue was flash column chromatographed with 15% of (10/1) mixture of MeOH/NH4OH in CHCl3 to give titled compound (236 mg, 77%).

Workup

  1. stirringwas stirred for 16 hours
  2. customThe solvent was removed in vacuo
  3. customchromatographed with 15% of (10/1) mixture of MeOH/NH4OH in CHCl3

Sources & evidence

ORD record
ord-36d30a7746574e089c433f1efd038d11
Source dataset
uspto-grants-1992_09
Patent number
US05151435

Reaction notes

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