HCID 25070138, compound → HCID 59803137, compound

HRID 929514Notes

Reaction equation

HRID 929514 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:25])[NH:11][CH:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)=[CH:5][CH:4]=1>Cl>[NH:15]1[CH2:16][CH2:17][CH:12]([NH:11][C:10]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:26])[F:27])=[CH:4][CH:5]=2)=[O:25])[CH2:13][CH2:14]1

Participants

3

Reactant 1

HCID 25070138HCID 25070138, compound

Product 1

HCID 59803137HCID 59803137, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

tert-butyl 4-(3-(4-(trifluoromethyl)phenyl)ureido)piperidine-1-carboxylate (1.6 g, 4.13 mmol) was dissolved in HCl solution (2M, MeOH, 100 mL). The resulting solution was refluxed for 2 h. The solvent was removed under vacuo and the crude was basified by NaOH solution (2N). The final precipitates (0.9 g, 3.13 mmol, 78%) were filtered and dried under high vacuum. The final product (PTU) was served as a scaffold for the following urea inhibitors synthesis. 1H NMR (d6-DMSO, 300 Mhz): δ 8.77 (s, 1H), 7.57 (s, 4H), 6.30 (d, J=7.8 Hz, 1H), 3.55 (m, 1H), 2.91 (d, J=12.6 Hz, 2H), 2.48 (d, J=11.1 Hz, 2H), 1.77 (d, J=11 Hz, 2H), 1.22 (m, 2H)

Workup

  1. temperatureThe resulting solution was refluxed for 2 h
  2. customThe solvent was removed under vacuo
  3. customThe final precipitates (0.9 g, 3.13 mmol, 78%)
  4. filtrationwere filtered
  5. customdried under high vacuum
  6. customThe final product (PTU) was served as a scaffold for the following urea inhibitors synthesis

Sources & evidence

ORD record
ord-1a267d49531e453f9bfffe61ce3f5ece
Source dataset
uspto-grants-2016_03
Patent number
US09296693B2

Reaction notes

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