Hydrochloric Acid → HCID 178489125, 화합물

HRID 271100노트

반응식

HRID 271100 반응식
[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]([NH2:18])=[CH:8][CH:7]=1.[N:19]([O-])=O.[Na+].Cl.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([C:34]2[CH2:35][C:36](=[O:39])[NH:37][N:38]=2)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33].C([O-])(=O)C.[Na+]>O.C(O)C>[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]([NH:18][N:19]=[C:35]2[C:34]([C:28]3[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:26]([O:25][CH3:24])[CH:27]=3)=[N:38][NH:37][C:36]2=[O:39])=[CH:8][CH:7]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 152835193-(3,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-5-oneHCID 223532056-(3-Bromo-propoxy)-biphenyl-3-ylamineHCID 23668193Sodium Nitrite

생성물 1

HCID 178489125HCID 178489125, 화합물수율 27.2%

시약·촉매·용매 1

HCID 19096565Water ethanol용매2회

실험 절차

6-(3-Bromo-propoxy)-biphenyl-3-ylamine (r, 250 mg, 0.82 mmol) was diazotized with sodium nitrite (67 mg, 0.98 mmol) in 1:1 water/ethanol and 0.5 mL concentrated HCl at 0° C. After approximately 1 hour, the diazonium solution was added dropwise to a suspension of 5-(3,4-dimethoxy-phenyl)-2,4-dihydro-pyrazol-3-one (200 mg, 0.9 mmol) and sodium acetate (1.1 g) in 10 mL 1:1 water/ethanol. The orange solid which precipitated was filtered and washed with water and dried. The crude product was purified by silica gel chromatography (eluent: 5% methanol/DCM) to afford 120 mg of 4-{[6-(3-bromo-propoxy)-biphenyl-3-yl]-hydrazono}-5-(3,4-dimethoxy-phenyl)-2,4-dihydro-pyrazol-3-one (s): HPLC (Rt) 5.02 min; m/e 536.1, MS (ES+): 538.9; 1H NMR (500 MHz, CDCl3): 13.9 (bs, 1H), 9.0 (bs, 1H), 7.7-6.9 (m, 11H), 4.1 (m, 2H), 3.9 (s, 3H), 3.7 (s, 3H), 3.5 (m, 2H), 3.3 (m, 2H), 2.2 (m, 2H) and 2.1 (m, 2H).

후처리

  1. customThe orange solid which precipitated
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried
  5. customThe crude product was purified by silica gel chromatography (eluent: 5% methanol/DCM)

출처 및 근거

ORD 기록
ord-2f0e308716c141d98ad61776008d5fa0
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452873B2

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