Oxalyl chloride → N3-(5-Chlorothiophen-2-ylcarbonyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethyl]-2,3-pyridinediamine

HRID 49843

反応式

HRID 49843 の反応式
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[N:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][CH:25]([CH2:28][NH:29][C:30]3[C:35]([NH2:36])=[CH:34][CH:33]=[CH:32][N:31]=3)[CH2:24][CH2:23]2)=[CH:18][CH:17]=1>C(Cl)Cl.CN(C=O)C.N1C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:36][C:35]2[C:30]([NH:29][CH2:28][CH:25]3[CH2:26][CH2:27][N:22]([C:19]4[CH:18]=[CH:17][N:16]=[CH:21][CH:20]=4)[CH2:23][CH2:24]3)=[N:31][CH:32]=[CH:33][CH:34]=2)=[O:9])=[CH:4][CH:3]=1

参加物

8

反応物 3

HCID 65578Oxalyl chlorideHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 12150690N2-[1-(4-pyridyl)piperidin-4-ylmethyl]-2,3-pyridinediamine

生成物 1

HCID 12990572N3-(5-Chlorothiophen-2-ylcarbonyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethyl]-2,3-pyridinediamine収率 62.3%

試薬・触媒・溶媒 4

HCID 1049Pyridine溶媒HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 5-chlorothiophene-2-carboxylic acid (120 mg, 0.72 mmol) in methylene chloride and DMF (0.005 mL) was treated with oxalyl chloride (0.105 mL, 1.20 mmol). After 0.25 h, the mixture was concentrated and the residue was dissolved in chloroform. This solution was added dropwise to a solution of N2-[1-(4-pyridyl)piperidin-4-ylmethyl]-2,3-pyridinediamine (170 mg, 0.6 mmol) in pyridine and chloroform. The reaction mixture was then purified using a procedure similar to that described in Example 2, Part D, yielding 160 mg (58%) of the title compound as a hydrochloride salt.

後処理

  1. concentrationthe mixture was concentrated
  2. dissolutionthe residue was dissolved in chloroform
  3. customThe reaction mixture was then purified

出典と根拠

ORDレコード
ord-0208a0524ee5473484eeef0ced84e59f
出典データセット
uspto-grants-2004_03
特許番号
US06710057B2

関連ノート

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