Trifluoroacetic acid → N-(2,6-diethylphenyl)-8-({2-methoxy-4-[(1-methylpiperidin-4-yl)amino]phenyl}amino)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 81969

반응식

HRID 81969 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:18]=[CH:17][C:16]3[CH2:15][CH2:14][C:13]4[C:19]([C:23]([NH:25][C:26]5[C:31]([CH2:32][CH3:33])=[CH:30][CH:29]=[CH:28][C:27]=5[CH2:34][CH3:35])=[O:24])=[N:20][N:21]([CH3:22])[C:12]=4[C:11]=3[N:10]=2)=[C:4]([O:36][CH3:37])[CH:3]=1.O1[CH2:43][CH2:42][C:41](=O)[CH2:40][CH2:39]1.C(O)(C(F)(F)F)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[CH3:65][N+:66](C)(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:34]([C:27]1[CH:28]=[CH:29][CH:30]=[C:31]([CH2:32][CH3:33])[C:26]=1[NH:25][C:23]([C:19]1[C:13]2[CH2:14][CH2:15][C:16]3[CH:17]=[N:18][C:9]([NH:8][C:5]4[CH:6]=[CH:7][C:2]([NH:1][CH:41]5[CH2:42][CH2:43][N:66]([CH3:65])[CH2:39][CH2:40]5)=[CH:3][C:4]=4[O:36][CH3:37])=[N:10][C:11]=3[C:12]=2[N:21]([CH3:22])[N:20]=1)=[O:24])[CH3:35]

참가 물질

7

반응물 5

HCID 6422Trifluoroacetic acidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 516892Sodium BicarbonateHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)HCID 670760398-[(4-amino-2-methoxyphenyl)amino]-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

생성물 1

HCID 44556121N-(2,6-diethylphenyl)-8-({2-methoxy-4-[(1-methylpiperidin-4-yl)amino]phenyl}amino)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide수율 34%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 8-[(4-amino-2-methoxyphenyl)amino]-N-(2,6-diethylphenyl)-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (80 mg, 0.158 mmol) in 1.5 ml of CH2Cl2 under argon atmosphere, tetrahydro-4H-pyran-4-one (20 mg, 0.198 mmol), TFA (0.428 mmol; 2.7 eq) and tetramethylammonium triacetoxyborohydride (63 mg, 0.238 mmol) were added. The mixture was stirred at room temperature for 1 h. Saturated aqueous NaHCO3 was added and the organic layer separated, dried on anhydrous Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (97.5/2.5 CH2Cl2/CH3OH) giving the to desired product as a brown foam in a 34% yield.

후처리

  1. customthe organic layer separated
  2. dry with materialdried on anhydrous Na2SO4
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography (97.5/2.5 CH2Cl2/CH3OH)

출처 및 근거

ORD 기록
ord-aced4729a7324df7b9c6d4aaf5f74eaa
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846701B2

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