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

HRID 30064
Notes
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Reaction equation

HRID 30064 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-72bf44b82f584085a2e47d40530dd312
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07423030B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes