HCID 49780163, compound → HCID 49780164, compound

HRID 574684Notes

Reaction equation

HRID 574684 reaction equation
[F:1][C:2]([F:28])([F:27])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:26])[NH:12][CH:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[CH:6][CH:5]=1>Cl>[NH:16]1[CH2:17][CH2:18][CH:13]([NH:12][C:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:1])([F:27])[F:28])=[CH:5][CH:6]=2)=[O:26])[CH2:14][CH2:15]1

Participants

3

Reactant 1

HCID 49780163HCID 49780163, compound

Product 1

HCID 49780164HCID 49780164, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

tert-butyl 4-(3-(4-(trifluoromethoxy)phenyl)ureido)piperidine-1-carboxylate (7.5 g, 18.6 mmol) was dissolved in HCl solution (2 M, MeOH, 100 mL). The resulting solution was refluxed for 2 h. The solvent was removed under vacuo and the crude was washed by dichloromethane twice and was basified to pH 10 by NaOH solution (6N). The final precipitates (5.6 g, 18.5 mmol, 99%) were filtered and dried under high vacuum. The final product (PTU/2) was served as a scaffold for the following urea inhibitors synthesis. 1H NMR (d6-DMSO, 300 Mhz): ∂ 1.19 (m, 2H), 1.74 (d, J=9 Hz, 2H), 2.10 (br, 1H), 2.48 (m, 2H), 2.87 (d, J=9 Hz, 2H), 2.90 (m, 1H), 6.18 (d, J=8 Hz, 1H), 7.20 (d, J=9 Hz, 2H), 7.46 (d, J=9 Hz, 2H), 8.52 (s, 1H). 19F NMR (d6-DMSO, 300 Mhz): ∂ 57.17.

Workup

  1. temperatureThe resulting solution was refluxed for 2 h
  2. customThe solvent was removed under vacuo
  3. washthe crude was washed by dichloromethane twice
  4. customThe final precipitates (5.6 g, 18.5 mmol, 99%)
  5. filtrationwere filtered
  6. customdried under high vacuum
  7. customThe final product (PTU/2) was served as a scaffold for the following urea inhibitors synthesis

Sources & evidence

ORD record
ord-b41d3f68298047adb37f985db23b368c
Source dataset
uspto-grants-2015_05
Patent number
US09034903B2

Reaction notes

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