HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 2300170
Notes
Print preview

Reaction equation

HRID 2300170 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-9a27681a38044ce3b2388f023b70448e
Source dataset
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06498159B1

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes