Sodium Bicarbonate → 6-cyano-N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 706611Notes

Reaction equation

HRID 706611 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]([O-:14])=O)=[CH:10][N:11]=2)[CH:8]=1)#[N:2].[Li+].ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.[CH3:28][C:29]1[C:37]2[C:36]([NH2:38])=[CH:35][CH:34]=[CH:33][C:32]=2[N:31]([CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([CH3:46])[N:41]=2)[N:30]=1.C(=O)(O)[O-].[Na+]>CN1C(=O)CCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:7]([C:9]([C:12]([NH:38][C:36]3[CH:35]=[CH:34][CH:33]=[C:32]4[C:37]=3[C:29]([CH3:28])=[N:30][N:31]4[CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([CH3:46])[N:41]=3)=[O:14])=[CH:10][N:11]=2)[CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 67260216Lithium 6-cyanoimidazo[1,2-a]pyridine-3-carboxylateHCID 672609383-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine

Product 1

HCID 573869006-cyano-N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideYield 47.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Lithium 6-cyanoimidazo[1,2-a]pyridine-3-carboxylate (138 mg, 0.7 mmol) was dissolved in anhydrous NMP (3.6 mL) and 2,4,6-trichlorobenzoyl chloride (115 mL, 0.7 mmol) added drop-wise. The mixture was stirred at ambient temperature for 30 minutes. 3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (186 mg, 0.7 mmol) was then added in one portion and the reaction heated to 80° C. in a sand bath for 6 hours. Saturated sodium bicarbonate was added until precipitate formed and allowed to stir at ambient temperature for an hour. The precipitate was filtered off and dried under high vacuum for 2 hours to give 6-cyano-N-(3-methyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide as a beige solid (140 mg). MS m/z 422.3 (M+1, APCI+).

Workup

  1. temperaturethe reaction heated to 80° C. in a sand bath for 6 hours
  2. customformed
  3. stirringto stir at ambient temperature for an hour
  4. filtrationThe precipitate was filtered off
  5. customdried under high vacuum for 2 hours

Sources & evidence

ORD record
ord-ed260d57dcf04556b95089b254bb7753
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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