Hydrochloric Acid → (6-Bromo-3-nitro-quinolin-4-yl)-(1,3-dimethyl-1H-pyrazol-4-yl)-amine

HRID 445539

反応式

HRID 445539 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2Cl.[NH2:16][C:17]1[C:18]([CH3:23])=[N:19][N:20]([CH3:22])[CH:21]=1.Cl.CN1C(C)(C)CCCC1(C)C>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2[NH:16][C:17]1[C:18]([CH3:23])=[N:19][N:20]([CH3:22])[CH:21]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6603PempidineHCID 44310561,3-dimethyl-1H-pyrazol-4-amineHCID 219841286-Bromo-4-chloro-3-nitroquinoline

生成物 1

HCID 59619997(6-Bromo-3-nitro-quinolin-4-yl)-(1,3-dimethyl-1H-pyrazol-4-yl)-amine

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
50 °C

実験手順

To a mixture of 6-bromo-4-chloro-3-nitro-quinoline (Stage A.4, 3.0 g, 20.43 mmol) and 4-amino-1,3-dimethylpyrazole.HCl (ChemCollect, Remscheid, Germany, 1.85 g, 12.53 mmol) in DMA (45 ml) was added 1,2,2,6,6-pentamethylpiperidine (6.67 ml, 36.5 mmol). The RM was stirred at 50° C. for 4.5 h. Then the RM was cooled down to rt and quenched with H2O. The suspension was filtered, the solid cake was washed with H2O and dried under vacuum, before being dissolved in EtOAc. The solution was washed with brine (2×), dried over Na2SO4, filtered and evaporated to dryness to give the title compound as an orange solid (HPLC tR 2.55 min (Method A); M+H=362; M−H=360 MS-ES)

後処理

  1. temperatureThen the RM was cooled down to rt
  2. customquenched with H2O
  3. filtrationThe suspension was filtered
  4. washthe solid cake was washed with H2O
  5. customdried under vacuum
  6. dissolutionbefore being dissolved in EtOAc
  7. washThe solution was washed with brine (2×)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated to dryness

出典と根拠

ORDレコード
ord-107e0d394ec241819ab4fdd628a3d338
出典データセット
uspto-grants-2013_07
特許番号
US08476294B2

関連ノート

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