Trifluoroacetic acid → N-(4-amino-2-methyl-6-(((1-methylethyl)amino)carbonyl)phenyl)-1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

HRID 1983073ノート

反応式

HRID 1983073 の反応式
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([NH:15][C:16]3[C:21]([C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])=[CH:20][C:19]([N+:28]([O-])=O)=[CH:18][C:17]=3[CH3:31])=[O:14])=[CH:11][C:10]([C:32]([F:35])([F:34])[F:33])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(O)=O>ClCCl.[Zn]>[NH2:28][C:19]1[CH:20]=[C:21]([C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])[C:16]([NH:15][C:13]([C:12]2[N:8]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=3)[N:9]=[C:10]([C:32]([F:35])([F:34])[F:33])[CH:11]=2)=[O:14])=[C:17]([CH3:31])[CH:18]=1

参加物

5

反応物 2

HCID 6422Trifluoroacetic acidHCID 18446929HCID 18446929、化合物

生成物 1

HCID 10227689N-(4-amino-2-methyl-6-(((1-methylethyl)amino)carbonyl)phenyl)-1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

Zinc dust (90 mg, 1.4 mmol) was added to a solution of the product from Step C (70 mg, 0.14 mmole) and trifluoroacetic acid (2 mL) at 70° C. Some foaming occurred. After 10 minutes at 70° C., the mixture was cooled to 25° C., diluted with dichloromethane, and filtered. The filtrate was concentrated to remove most of the trifluoroacetic acid and the resulting residue was dissolved in acetonitrile (3 mL) and 1,2-dichloroethane (3 mL). The resulting solution was treated with strongly-basic ion exchange resin (Dowex® 550A, OH− form, 2 g), shaken for 1 hour and then filtered. Concentration of the filtrate gave the title compound, a compound of the invention, as a yellow solid.

後処理

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customto remove most of the trifluoroacetic acid
  4. dissolutionthe resulting residue was dissolved in acetonitrile (3 mL)
  5. additionThe resulting solution was treated with strongly-basic ion exchange resin (Dowex® 550A, OH− form, 2 g)
  6. filtrationfiltered

出典と根拠

ORDレコード
ord-9d1279655f4044c98ffb1af6556b9d0c
出典データセット
uspto-grants-2009_06
特許番号
US07541377B2

反応ノート

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