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1-Hydroxybenzotriazole → 8-Hydroxy-N-methyl-N-(4-(2-phenylpropan-2-yl)benzyl)quinoline-2-carboxamide

HRID 1025542
Notes
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Reaction equation

HRID 1025542 reaction equation
CCN=C=N[CH2:6][CH2:7][CH2:8][N:9]([CH3:11])[CH3:10].Cl.C1C=CC2N([OH:22])N=NC=2C=1.CNCC1[CH:31]=[CH:30][C:29]([C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([CH3:34])[CH3:33])=[CH:28]C=1.[OH:41][C:42]1[C:43](C(O)=O)=[CH:44][CH:45]=[C:46]2[C:51]=1[N:50]=[CH:49][CH:48]=[CH:47]2>C(Cl)Cl>[OH:41][C:42]1[CH:43]=[CH:44][CH:45]=[C:46]2[C:51]=1[N:50]=[C:49]([C:11]([N:9]([CH3:10])[CH2:8][C:7]1[CH:6]=[CH:28][C:29]([C:32]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)([CH3:33])[CH3:34])=[CH:30][CH:31]=1)=[O:22])[CH:48]=[CH:47]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 2313638-Hydroxyquinoline-7-carboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18333891N-[4-(1-Methyl-1-phenylethyl)benzyl]-methylamine

Product 1

HCID 672931388-Hydroxy-N-methyl-N-(4-(2-phenylpropan-2-yl)benzyl)quinoline-2-carboxamide
Yield 47.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TEA (42 mg, 0.42 mmol), EDC.HCl (80 mg, 0.42 mmol), HOBt (57 mg, 0.418 mmol) and N-methyl-1-(4-(2-phenylpropan-2-yl)phenyl)methanamine (50 mg, 0.21 mmol) of Preparation 1 were sequentially added to a suspension of 8-hydroxyquinoline-7-carboxylic acid (48 mg, 0.25 mmol) in DCM (2.5 mL). The resulting reaction mixture was stirred at RT overnight. The mixture was quenched with H2O and then extracted three times with DCM. The separated organics were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, DCM:MeOH 95:5) affording the title compound (39 mg, 0.1 mmol) as a grey solid. LC-MS m/z (ESI+): 411.2 (MH+), Rt=2.42 min (Method A).

Workup

  1. customThe resulting reaction mixture
  2. customThe mixture was quenched with H2O
  3. extractionextracted three times with DCM
  4. dry with materialThe separated organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (silica gel, DCM:MeOH 95:5)

Sources & evidence

ORD record
ord-2f4323f60f0343f0b75e2947b552144f
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08729098B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes