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Tin dichloride dihydrate → 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-aminophenyl)piperidin-3-ol

HRID 1392415
Notes
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Reaction equation

HRID 1392415 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1([C:15]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[N+:31]([O-])=O)[CH2:20][CH:19]2[OH:34])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7].O.[Sn](Cl)Cl>C(O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]1([C:15]([NH:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=3[NH2:31])[CH2:20][CH:19]2[OH:34])=[O:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 43835034Tin dichloride dihydrateHCID 693102044-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-nitrophenyl)piperidin-3-ol

Product 1

HCID 693103034-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-aminophenyl)piperidin-3-olYield 78.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To the solution of 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-nitrophenyl)piperidin-3-ol (7.0 g, 14.7 mmol) obtained in Step 1 in 70 ml of ethanol, was added tin (II) chloride hydrate (1.13 mg, 44.2 mmol). The reaction mixture was refluxed for about 4 hours at 80° C., and then cooled to room temperature and concentrated. The resulting residue was diluted with 100 ml of ethyl acetate, alkalized with 29% aqueous ammonia solution (pH 8), and then the resulting white solid was filtered out. 100 ml of distilled water was added to the resulting filtrate. The resulting organic layer was dried and concentrated on sodium sulfate to give the titled compound (5.1 g).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. additionThe resulting residue was diluted with 100 ml of ethyl acetate
  4. filtrationthe resulting white solid was filtered out
  5. addition100 ml of distilled water was added to the resulting filtrate
  6. customThe resulting organic layer was dried
  7. concentrationconcentrated on sodium sulfate

Sources & evidence

ORD record
ord-a4c00ecc03d1468c8ccd71128c4dd465
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07342027B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes