Dimethylformamide → 6-amino-5-cyano-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)imidazo[1,2-a]pyridine-8-carboxamide

HRID 2407743Notes

Reaction equation

HRID 2407743 reaction equation
[N:1]1(O)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=N1.[CH2:11]([N:13](CC)CC)[CH3:12].C([N:20]=C=NCCCN(C)C)C.Cl.Cl.Cl.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:38]1[S:39][C:40]([CH2:43][N:44]2[CH2:49][CH2:48][CH:47]([CH2:50][NH2:51])[CH2:46][CH2:45]2)=[CH:41][N:42]=1.CN(C)[CH:54]=[O:55]>C(=O)([O-])O.[Na+]>[NH2:20][C:8]1[CH:7]=[C:6]([C:54]([NH:51][CH2:50][CH:47]2[CH2:46][CH2:45][N:44]([CH2:43][C:40]3[S:39][C:38]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=4)=[N:42][CH:41]=3)[CH2:49][CH2:48]2)=[O:55])[C:5]2[N:1]([CH:12]=[CH:11][N:13]=2)[C:9]=1[C:4]#[N:3]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471Triethylamine2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-Hydroxybenzotriazole2×HCID 66989375(1-((2-(Pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methanamine Trihydrochloride2×

Product 1

HCID 585041036-amino-5-cyano-N-((1-((2-(pyridin-2-yl)thiazol-5-yl)methyl)piperidin-4-yl)methyl)imidazo[1,2-a]pyridine-8-carboxamide

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
40 °C

Procedure

This material was then combined with 1H-benzo[d][1,2,3]triazol-1-ol (0.012 g), and triethylamine (0.0613 mL) in N,N-dimethylformamide (0.5 mL). 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (0.0145 g) was then added to the reaction mixture. After stirring for 30 minutes, the compound prepared in Example 214 (0.030 g) was added to the reaction mixture. The reaction mixture was allowed to stir at room temperature for 3 hours. Equivalent amounts of 1H-benzo[d][1,2,3]triazol-1-ol, triethylamine, and the compound prepared in Example 214 were added to the reaction mixture, and then heated at 40° C. for 17 hours. The reaction mixture was diluted with saturated sodium hydrogen carbonate aqueous solution and extracted with ethyl acetate. The combined organics were then washed with water and brine, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=19:1) to obtain the title compound (0.0085 g) having the following physical data.

Workup

  1. stirringto stir at room temperature for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organics were then washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=19:1)

Sources & evidence

ORD record
ord-d44912bbdfa247039335da765ad28bd1
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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