Triphenyl phosphite → HCID 178451788, compound

HRID 1913144Notes

Reaction equation

HRID 1913144 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([C:23](O)=O)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>N1C=CC=CC=1.CCOC(C)=O>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([C:23]2[NH:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=3[N:9]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 3

HCID 7540Triphenyl phosphiteHCID 1645844-Fluorobenzene-1,2-diamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 178451788HCID 178451788, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

This compound is synthesized as described by adaptation of the following reference: Lin et al, Tetrahedron Lett., 2006, 47, 17, 2883. To a stirred mixture of 4-fluorobenzene-1,2-diamine (1.0 g, 7.93 mmol) and 1-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid (1.82 g, 7.93 mmol) in pyridine (4 mL) is added triphenyl phosphite (2.49 mL, 9.51 mmol). The reaction mixture is heated under reflux for 18 h. The reaction mixture is cooled to room temperature and diluted with EtOAc (40 mL). The solution is washed with 1M aqueous HCl (8 mL) followed by saturated aqueous NaHCO3 (8 mL) and water (5 mL) to give an oily residue. The crude product is purified by column chromatography (Isolute column, eluent: DCM, 3% MeOH) to afford 0.81 g of tert-butyl-4-(5-fluoro-1H-1,3-benzodiazol-2-yl)piperidine-1-carboxylate.

Workup

  1. customThis compound is synthesized
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux for 18 h
  4. washThe solution is washed with 1M aqueous HCl (8 mL)
  5. customto give an oily residue
  6. customThe crude product is purified by column chromatography (Isolute column, eluent: DCM, 3% MeOH)

Sources & evidence

ORD record
ord-b5bb068511b74463b658fe3e240d3ce3
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

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