Oxalyl chloride → N-(5-cyano-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 1045399

反応式

HRID 1045399 の反応式
[N:1]1[CH:2]=[C:3]([C:10]([OH:12])=O)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(Cl)(=O)C(Cl)=O.[NH2:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[CH3:28])[C:23]#[N:24]>ClCCl.CN(C=O)C.CO.ClC(Cl)C.N(CC)(CCC)CCC>[C:23]([C:22]1[CH:25]=[CH:26][C:27]([CH3:28])=[C:20]([NH:19][C:10]([C:3]2[N:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]3=[N:1][CH:2]=2)=[O:12])[CH:21]=1)#[N:24]

参加物

9

反応物 3

HCID 65578Oxalyl chlorideHCID 73142Imidazo(1,2-a)pyridine-3-carboxylic acidHCID 70164283-Amino-4-methylbenzonitrile

生成物 1

HCID 71280318N-(5-cyano-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide収率 35.5%

試薬・触媒・溶媒 5

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 63651,1-Dichloroethane溶媒2 回HCID 519799N,N-Dipropylethylamine溶媒

実験手順

To a suspension of imidazo[1,2-a]pyridine-3-carboxylic acid (1) (16.6 g, 102 mmol) in dichloromethane (300 mL) and DMF (0.5 mL) at 0° C. was added oxalyl chloride (45 mL, 510 mmol) dropwise over 10 minutes. The reaction was slowly warmed to room temperature and stirred until complete conversion was detected by LCMS in MeOH. The reaction was subsequently reduced to dryness and suspended in dichloroethane (100 mL) and was added to a solution of 3-amino-4-methylbenzonitrile (7) (15 g, 113 mmol) in dichloroethane (200 mL) and Pr2NEt (55 mL) at 0° C. After the addition, the cold bath was removed and contents were stirred at room temperature for 1 hour and then heated to 50° C. for another 2 hours. After the completion of the reaction, the mixture was cooled and a white precipitate formed. The mixture was filtered and the solid was washed with cold dichloromethane. About 10 g of the desired N-(5-cyano-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (8) was obtained. The filtrate was washed with saturated NH4Cl, saturated NaHCO3, brine, dried over magnesium sulfate, filtered and reduced to dryness. The crude solid was triturated with diethyl ether to remove excess aniline and filtered to afford another crop of N-(5-cyano-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (8) as a white solid. MS m/z 277.1 (M+1).

後処理

  1. additionAfter the addition
  2. customthe cold bath was removed
  3. stirringcontents were stirred at room temperature for 1 hour
  4. temperatureheated to 50° C. for another 2 hours
  5. customAfter the completion of the reaction
  6. temperaturethe mixture was cooled
  7. customa white precipitate formed
  8. filtrationThe mixture was filtered
  9. washthe solid was washed with cold dichloromethane

出典と根拠

ORDレコード
ord-c75688a182f44091a80eae657f0ef4fe
出典データセット
uspto-grants-2013_10
特許番号
US08569283B2

関連ノート

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