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Pyridine → 9H-fluoren-9-ylmethyl(2,4-dimethyl-5-{[(pyridin-3-ylmethyl)amino]sulfonyl}phenyl)carbamate

HRID 1802462
Notes
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Reaction equation

HRID 1802462 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:30])[NH:17][C:18]3[CH:23]=[C:22]([S:24](Cl)(=[O:26])=[O:25])[C:21]([CH3:28])=[CH:20][C:19]=3[CH3:29])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][NH2:38])[CH:32]=1.N1C=CC=CC=1>C(Cl)Cl>[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16](=[O:30])[NH:17][C:18]3[CH:23]=[C:22]([S:24]([NH:38][CH2:37][C:33]4[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=4)(=[O:26])=[O:25])[C:21]([CH3:28])=[CH:20][C:19]=3[CH3:29])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 310183-PyridinemethanamineHCID 594360429h-Fluoren-9-ylmethyl[5-(chlorosulfonyl)-2,4-dimethylphenyl]carbamate

Product 1

HCID 594361089H-fluoren-9-ylmethyl(2,4-dimethyl-5-{[(pyridin-3-ylmethyl)amino]sulfonyl}phenyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9H-fluoren-9-ylmethyl[5-(chlorosulfonyl)-2,4-dimethylphenyl]carbamate (1.0 g, 2.3 mmol) in CH2Cl2 (23 mL) was added 1-pyridin-3-ylmethanamine (0.46 mL, 4.5 mmol) and pyridine (0.55 mL, 6.8 mmol). The bright yellow solution was then stirred at room temperature overnight and then quenched by the addition of sat. aq. NaHCO3 solution. The reaction was extracted with EtOAc and the organic extracted were dried over Na2SO4 and concentrated in vacuo. Purification by silica gel column chromatography (0-5% MeOH/DCM) afforded the title compound.

Workup

  1. customquenched by the addition of sat. aq. NaHCO3 solution
  2. extractionThe reaction was extracted with EtOAc
  3. extractionthe organic extracted
  4. dry with materialwere dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel column chromatography (0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-e8510aed1e0d46bbb3cafaee6328fe98
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08349865B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes