Ammonia → N-{4-[(4-{[7-Methoxy-4-(4-methoxyphenyl)phthalazin-1-yl]amino}piperidin-1-yl)methyl]phenyl}carboxamide dihydrochloride

HRID 30064

반응식

HRID 30064 반응식
C([N:3]1[CH2:8]COCC1)C.[CH3:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([C:38]3[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=3)=[N:16][N:17]=[C:18]2[NH:21][CH:22]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[CH:34]=[CH:33][C:32](C(O)=O)=[CH:31][CH:30]=3)[CH2:24][CH2:23]2)=[CH:13][CH:12]=1.[Cl:46]C(OCC)=[O:48].N>O1CCCC1>[ClH:46].[ClH:46].[CH3:9][O:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([C:38]3[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=3)=[N:16][N:17]=[C:18]2[NH:21][CH:22]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([NH:3][CH:8]=[O:48])=[CH:31][CH:30]=3)[CH2:24][CH2:23]2)=[CH:13][CH:12]=1

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 7525EthylmorpholineHCID 10928Ethyl chloroformateHCID 69211746{4-[(4-{[7-Methoxy-4-(4-methoxyphenyl)phthalazin-1-yl]amino}piperidin-1-yl)methyl]phenyl}carboxylic acid

생성물 1

HCID 87736134N-{4-[(4-{[7-Methoxy-4-(4-methoxyphenyl)phthalazin-1-yl]amino}piperidin-1-yl)methyl]phenyl}carboxamide dihydrochloride수율 68.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

0.29 mL (2.3 mmol) of N-ethylmorpholine is added to a stirred suspension of 400 mg (0.7 mmol) of {4-[(4-{[7-methoxy-4-(4-methoxyphenyl)phthalazin-1-yl]amino}piperidin-1-yl)methyl]phenyl}carboxylic acid (dihydrochloride) in 10 mL of tetrahydrofuran at 0° C., followed by dropwise addition of 0.074 mL (0.77 mmol) of ethyl chloroformate. The mixture is stirred for 1 hour at 0° C., and 0.6 mL (3.5 mmol) of a 20% aqueous ammonia solution is then added slowly. The reaction medium is stirred for 20 hours at room temperature and is then concentrated under reduced pressure. 1N sodium hydroxide is added to the residue and the mixture is then extracted with dichloromethane. The organic phase is washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then evaporated under reduced pressure. The residue is purified on a column of silica (eluent: 85/15 (v/v) dichloromethane/methanol). 150 mg of a colourless oil are obtained.

후처리

  1. stirringThe reaction medium is stirred for 20 hours at room temperature
  2. concentrationis then concentrated under reduced pressure
  3. addition1N sodium hydroxide is added to the residue
  4. extractionthe mixture is then extracted with dichloromethane
  5. washThe organic phase is washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue is purified on a column of silica (eluent: 85/15 (v/v) dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-72bf44b82f584085a2e47d40530dd312
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423030B2

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