Ammonia → 1-(3-Methylanilino)-4-(4-pyridylmethyl)phthalazine

HRID 1057700

반응식

HRID 1057700 반응식
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.Cl.C(N(CC)CC)C.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[CH:25]=1.[N:31]1[CH:36]=[CH:35][C:34]([CH2:37][C:38]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:41](=O)[NH:40][N:39]=2)=[CH:33][CH:32]=1.CN(C)C(=O)N(C)C.N>O.ClCCl>[CH3:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[NH:23][C:41]1[C:42]2[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:38]([CH2:37][C:34]2[CH:35]=[CH:36][N:31]=[CH:32][CH:33]=2)=[N:39][N:40]=1

참가 물질

9

반응물 6

HCID 222AmmoniaHCID 7934m-ToluidineHCID 11130Triethylamine hydrochlorideHCID 12437TetramethylureaHCID 14812Phosphorus oxide (P4O10)HCID 7899544-(4-Pyridylmethyl)-1(2H)-phtalazinone

생성물 1

HCID 64193871-(3-Methylanilino)-4-(4-pyridylmethyl)phthalazine

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매

반응 조건

온도
200 °C

실험 절차

A mixture of 2.39 g (16,8 mmol) phosphorus pentoxide, 2.31 g (16,8 mmol) triethylamine hydrochloride, and 1.82 ml (16.8 mmol) m-toluidine is heated and stirred in a nitrogen atmosphere at 200° C. until a homogeneous melt has formed. To the melt, 1 g (4.2 mmol) 4-(4-pyridylmethyl)-1(2H)-phthalazinone is added and the reaction mixture stirred for a further 3.5 h at 205° C. After cooling to about 170° C., 4 ml tetramethylurea is added to the reaction mixture, followed by 2 ml water at about 110° C. The mixture is stirred for a further 30 min while cooling to RT and then distributed between dichloromethane and a mixture of 20 ml water and 5 ml conc. ammonia. The organic phase dried over sodium sulfate is concentrated by evaporation and the residue purified on silica gel by flash chromatography using acetate and acetate/methanol (99:1 and 19:1). Title compound is obtained after crystallization of the product-containing fractions from acetonitrile and subsequent recrystallization from acetate; m.p. 141-143° C.; ESI-MS: (M+H)+=327.

후처리

  1. temperatureis heated
  2. customhas formed
  3. stirringthe reaction mixture stirred for a further 3.5 h at 205° C
  4. temperatureAfter cooling to about 170° C.
  5. stirringThe mixture is stirred for a further 30 min
  6. temperaturewhile cooling to RT
  7. dry with materialThe organic phase dried over sodium sulfate
  8. concentrationis concentrated by evaporation
  9. customthe residue purified on silica gel by flash chromatography

출처 및 근거

ORD 기록
ord-1e794733e22b4bffa9659de9ed27b495
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514974B2

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