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

HRID 445539노트

반응식

HRID 445539 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
50 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-107e0d394ec241819ab4fdd628a3d338
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476294B2

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