Diisopropylethylamine → N-((1H-pyrazol-4-yl)methyl)-5-(2,4-dichloro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-Pyrazole-3-carboxamide

HRID 522083ノート

反応式

HRID 522083 の反応式
[Cl:1][C:2]1[CH:24]=[C:23]([Cl:25])[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)=[CH:21][C:3]=1[C:4]([NH:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[C:9]([C:18](O)=[O:19])[CH:8]=1)=[O:5].CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1C2C(=NC=CC=2)N(OC(N(C)C)=[N+](C)C)N=1.Cl.[NH:66]1[CH:70]=[C:69]([CH2:71][NH2:72])[CH:68]=[N:67]1>CN(C=O)C.C(OCC)(=O)C>[NH:66]1[CH:70]=[C:69]([CH2:71][NH:72][C:18]([C:9]2[CH:8]=[C:7]([NH:6][C:4](=[O:5])[C:3]3[CH:21]=[C:22]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)[C:23]([Cl:25])=[CH:24][C:2]=3[Cl:1])[N:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:10]=2)=[O:19])[CH:68]=[N:67]1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57415873(1H-Pyrazol-4-yl)methanamine hydrochlorideHCID 1184970355-(2,4-dichloro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid

生成物 1

HCID 118497139N-((1H-pyrazol-4-yl)methyl)-5-(2,4-dichloro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-Pyrazole-3-carboxamide収率 29%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To solution of 5-(2,4-dichloro-5-(pyridin-2-yl)benzamido)-1-phenyl-1H-pyrazole-3-carboxylic acid (Example 111, 200 mg, 0.44 mmol) in DMF was added DIPEA (0.46 mL, 2.65 mmol) and 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (201 mg, 0.53 mmol). The reaction was stirred at room temperature for 10 minutes before the addition of (1H-pyrazol-4-yl)methanamine hydrochloride (64 mg, 0.49 mmol). The reaction was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate (50 mL) and extracted with water (3×5 mL) and brine (25 mL). The organic layer was collected, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with 2% MeOH in DCM to afford the title compound (68 mg, 29%).

後処理

  1. extractionextracted with water (3×5 mL) and brine (25 mL)
  2. customThe organic layer was collected
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified
  6. washeluting with 2% MeOH in DCM

出典と根拠

ORDレコード
ord-a81401a587984acdb69b47d049cbc029
出典データセット
uspto-grants-2016_05
特許番号
US09328096B2

反応ノート

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