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

HRID 30064

反応式

HRID 30064 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-72bf44b82f584085a2e47d40530dd312
出典データセット
uspto-grants-2008_09
特許番号
US07423030B2

関連ノート

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