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Water → Benzyl 1-benzyl-2-oxo-6-phenyl-1,2,3,4-tetrahydro-1,7-naphthyridin-3-ylcarbamate

HRID 2221098
Notes
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Reaction equation

HRID 2221098 reaction equation
[O:1]=[C:2]1[CH:11]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][C:9]2[C:4](=[CH:5][N:6]=[C:7]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:8]=2)[NH:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:35](Br)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.O>CN(C=O)C>[CH2:35]([N:3]1[C:4]2[C:9](=[CH:8][C:7]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:6][CH:5]=2)[CH2:10][CH:11]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:2]1=[O:1])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 58671541HCID 58671541, compound

Product 1

HCID 11605071Benzyl 1-benzyl-2-oxo-6-phenyl-1,2,3,4-tetrahydro-1,7-naphthyridin-3-ylcarbamateYield 50.4%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3F (400 mg, 1.07 mmol) in DMF (8 mL) was added cesium carbonate (873 mg, 2.68 mmol), followed by benzyl bromide (0.38 mL, 3.21 mmol). The reaction mixture was stirred at 50° C. for 1 h. After cooling to RT, water (100 mL) was added. The reaction mixture was extracted with EtOAc (3×30 mL). During the extraction, some precipitates formed. The solid was collected by filtration and washed with EtOAc to give the title compound (250 mg). The combined organics were washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. The resultant residue was purified by silica gel (40 g) column chromatography eluting with a gradient of EtOAc (0-60%) in hexane to give additional 160 mg of the title compound (total 410 mg, 83%) as a white solid. LC/MS (method A): retention time=3.55 min, (M+H)+=464.

Workup

  1. temperatureAfter cooling to RT
  2. extractionThe reaction mixture was extracted with EtOAc (3×30 mL)
  3. extractionDuring the extraction
  4. customsome precipitates formed
  5. filtrationThe solid was collected by filtration
  6. washwashed with EtOAc

Sources & evidence

ORD record
ord-da5066a45f6e4ed9b5bd758502073685
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07368458B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes