Triethylamine → HCID 58486421、化合物

HRID 1890770ノート

反応式

HRID 1890770 の反応式
C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[F:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[N:53]=[N:52][C:51]([N:54]3[CH2:59][CH2:58][CH:57]([NH:60][CH3:61])[CH2:56][CH2:55]3)=[C:50]([CH3:62])[C:49]=2[CH3:63])=[CH:44][CH:43]=1.[CH3:64][O:65][C:66]1[CH:84]=[CH:83][C:69]([CH2:70][N:71]2[CH:75]=[C:74]([C:76](O)=[O:77])[C:73]([C:79]([F:82])([F:81])[F:80])=[N:72]2)=[CH:68][CH:67]=1>CN(C=O)C>[F:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[N:53]=[N:52][C:51]([N:54]3[CH2:59][CH2:58][CH:57]([N:60]([CH3:61])[C:76]([C:74]4[C:73]([C:79]([F:80])([F:81])[F:82])=[N:72][N:71]([CH2:70][C:69]5[CH:68]=[CH:67][C:66]([O:65][CH3:64])=[CH:84][CH:83]=5)[CH:75]=4)=[O:77])[CH2:56][CH2:55]3)=[C:50]([CH3:62])[C:49]=2[CH3:63])=[CH:44][CH:43]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 582442211-(4-Methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acidHCID 67368812HCID 67368812、化合物

生成物 1

HCID 58486421HCID 58486421、化合物収率 57%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Add PyBOP (343 mg, 0.65 mmol) and triethylamine (0.21 mL, 1.50 mmol) to a stirred solution of 1-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl)-N-methylpiperidin-4-amine (157 mg, 0.50 mmol) and 1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid (165 mg, 0.55 mmol) in anhydrous DMF (2.5 mL). Stir the resulting mixture at ambient temperature under N2 overnight. Concentrate, add MeOH, filter solids, and concentrate the filtrate. Dilute the residue with MeOH, and pour onto an SCX column (Thermo Scientific, 10 g). Wash with MeOH, and then elute the product with 2 M NH3/MeOH. Concentrate and purify by flash silica gel chromatography using a gradient of 0 to 10% (10% 2 M NH3/MeOH in EtOAc) in hexanes to obtain the title compound as a white solid (170 mg, 43%). ES/MS m/z 597.0 (M+1).

後処理

  1. concentrationConcentrate
  2. additionadd MeOH
  3. filtrationfilter solids
  4. concentrationconcentrate the filtrate
  5. additionDilute the residue with MeOH
  6. additionpour onto an SCX column (Thermo Scientific, 10 g)
  7. washWash with MeOH
  8. washelute the product with 2 M NH3/MeOH
  9. concentrationConcentrate
  10. custompurify by flash silica gel chromatography

出典と根拠

ORDレコード
ord-ba5e918971504885b64f597e5cf52f6b
出典データセット
uspto-grants-2013_08
特許番号
US08507490B2

反応ノート

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