1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18672408, compound

HRID 1058233Notes

Reaction equation

HRID 1058233 reaction equation
C1CCN2C(=NCCC2)CC1.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([CH:21]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[CH:22]([F:24])[F:23])=[C:17]([CH2:19]O)[CH:18]=1.C1C=CC(P([N:48]=[N+:49]=[N-:50])(C2C=CC=CC=2)=O)=CC=1>C1COCC1>[N:48]([CH2:19][C:17]1[CH:18]=[C:13]([Cl:12])[CH:14]=[CH:15][C:16]=1[CH:21]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[CH:22]([F:24])[F:23])=[N+:49]=[N-:50]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 18672411HCID 18672411, compound

Product 1

HCID 18672408HCID 18672408, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DBU (0.20 mL, 1.34 mmol) was added to a stirred solution of (5-chloro-2-{2,2-difluoro-1-[(4-methoxyphenyl)amino]ethyl}phenyl)methanol (0.439 g, 1.34 mmol) and DPPA (0.29 mL, 1.34 mmol) in THF (1.7 mL) at 0° C. and the mixture was warmed to ambient temperature. After 3 h the solution was partitioned between EtOAc (20 mL) and water (10 mL). The EtOAc layer was washed with 1M NaOH (10 mL) and brine (10 mL), dried (Na2SO4) and reduced in vacuo to give N-{1-[2-(azidomethyl)-4-chlorophenyl]-2,2-difluoroethyl}-N-(4-methoxyphenyl)amine (0.463 g) as an oil: MS 353.5 (M+1).

Workup

  1. customAfter 3 h the solution was partitioned between EtOAc (20 mL) and water (10 mL)
  2. washThe EtOAc layer was washed with 1M NaOH (10 mL) and brine (10 mL)
  3. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-5d5552c9faf64c098ff8ae6939d6bf19
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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