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Phthalimide → 4-(3-Chloro-4-methoxybenzyl)amino-6-cyano-1-(4-phthalimidopiperidino)phthalazine

HRID 47334
Notes
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Reaction equation

HRID 47334 reaction equation
N(C(OCC)=O)=NC(OCC)=O.O[CH:14]1[CH2:19][CH2:18][N:17]([C:20]2[C:29]3[C:24](=[CH:25][C:26]([C:30]#[N:31])=[CH:27][CH:28]=3)[C:23]([NH:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[C:36]([Cl:42])[CH:35]=3)=[N:22][N:21]=2)[CH2:16][CH2:15]1.[C:43]1(=[O:53])[NH:47][C:46](=[O:48])[C:45]2=[CH:49][CH:50]=[CH:51][CH:52]=[C:44]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Cl:42][C:36]1[CH:35]=[C:34]([CH:39]=[CH:38][C:37]=1[O:40][CH3:41])[CH2:33][NH:32][C:23]1[C:24]2[C:29](=[CH:28][CH:27]=[C:26]([C:30]#[N:31])[CH:25]=2)[C:20]([N:17]2[CH2:18][CH2:19][CH:14]([N:47]3[C:46](=[O:48])[C:45]4=[CH:49][CH:50]=[CH:51][CH:52]=[C:44]4[C:43]3=[O:53])[CH2:15][CH2:16]2)=[N:21][N:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9888568Yze9gcm2BB

Product 1

HCID 227445114-(3-Chloro-4-methoxybenzyl)amino-6-cyano-1-(4-phthalimidopiperidino)phthalazineYield 88.5%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Conditions

Temperature
4 °C

Procedure

Then, 30 ml solution of 3.48 g diethyl azodicarboxylate in tetrahydrofuran was added to 100 ml solution of 4.2 g 1-(4-hydroxypiperidino)-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine, 2.94 g phthalimide, and 5.24 g triphenylphosphine in tetrahydrofuran over 30 min under ice-cooling, and then it was stirred at 4° C. for 24 hr. The reaction solution was evaporated, water and ethyl acetate were added thereto, and then the insoluble matters were removed by filtration. The organic layer was concentrated, and the resulting residue was purified by silica gel column chromatography to give 4.85 g of 4-(3-chloro-4-methoxybenzyl)amino-6-cyano-1-(4-phthalimidopiperidino)phthalazine.

Workup

  1. temperaturecooling
  2. customThe reaction solution was evaporated
  3. additionwater and ethyl acetate were added
  4. customthe insoluble matters were removed by filtration
  5. concentrationThe organic layer was concentrated
  6. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3499b99806ee4668be7de89b733b6376
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06699870B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes