Triethylamine → [1-(4-Fluoro-phenylcarbamoyl)-4-(4-isopropyl-phenylcarbamoyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 1949086Notes

Reaction equation

HRID 1949086 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1([C:14](=[O:25])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[F:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[O:36])=[CH:30][CH:29]=1.CCN(CC)CC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1([C:14](=[O:25])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]([CH3:23])[CH3:24])=[CH:18][CH:17]=2)[CH2:9][CH2:10][N:11]([C:35](=[O:36])[NH:34][C:31]2[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=2)[CH2:12][CH2:13]1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 709554-Fluorophenyl isocyanateHCID 66921345[4-(4-Isopropyl-phenylcarbamoyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

Product 1

HCID 66921340[1-(4-Fluoro-phenylcarbamoyl)-4-(4-isopropyl-phenylcarbamoyl)-piperidin-4-yl]-carbamic acid tert-butyl esterYield 77.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 36 mg (0.1 mmol) [4-(4-Isopropyl-phenylcarbamoyl)-piperidin-4-yl]-carbamic acid tert-butyl ester, 16.5 mg (0.12 mmol) 4-fluorophenyl isocyanate and 32 mg (0.31 mmol) NEt3 in 1 mL DCM was shaken at room temperature over night. After evaporation to dryness the residue was subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and HCOOH. The product containing fractions were evaporated to yield 38.5 mg (77%) of the title compound. MS (m/e): 499.3 [(M+H)+].

Workup

  1. customAfter evaporation to dryness the residue
  2. customwas subjected to purification by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and HCOOH
  5. additionThe product containing fractions
  6. customwere evaporated

Sources & evidence

ORD record
ord-bfb8488c8f0a46aab38bc7203deb24ec
Source dataset
uspto-grants-2013_03
Patent number
US08399676B2

Reaction notes

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