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Water → 10-Morpholin-4-yl-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohepta[f]indene-7-carboxylic acid benzyl ester

HRID 528724
Notes
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Reaction equation

HRID 528724 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:25][CH2:24][C:15]2=[C:16](Cl)[N:17]3[C:21]([N:22]=[C:14]2[CH2:13][CH2:12]1)=[CH:20][CH:19]=[N:18]3)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.O>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:25][CH2:24][C:15]2=[C:16]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[N:17]3[C:21]([N:22]=[C:14]2[CH2:13][CH2:12]1)=[CH:20][CH:19]=[N:18]3)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 8666717110-Chloro-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohepta[f]indene-7-carboxylic acid benzyl ester

Product 1

HCID 6797929010-Morpholin-4-yl-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohepta[f]indene-7-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 702Ethanol
Solvent

Conditions

Temperature
60 °C

Procedure

To 0.15 g 10-chloro-5,6,8,9-tetrahydro-1,4,7,10a-tetraaza-cyclohepta[f]indene-7-carboxylic acid benzyl ester (0.42 mmol), in a sealed tube in 8 mL ethanol, was added 78 μL (0.88 mmol) morpholine, and the reaction was heated at 60° C. for 16 hours. 5 mL of H2O was added and the mixture was extracted with EtOAc (2×10 mL), the organic layers were combined and dried with MgSO4. After filtration and evaporation of the solvent the product was purified by column chromatography (silica, DCM/MeOH 2%).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×10 mL)
  2. dry with materialdried with MgSO4
  3. filtrationAfter filtration and evaporation of the solvent the product
  4. customwas purified by column chromatography (silica, DCM/MeOH 2%)

Sources & evidence

ORD record
ord-6befea2fa54c4220876f6377a5fe2f92
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09346816B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes