Triethylamine → N-(5-tert-Butylisoxazol-3-yl)-4-{[(3S)-1-cyclopropylpiperidin-3-yl]methyl}piperazine-1-carboxamide

HRID 603169Notes

Reaction equation

HRID 603169 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][CH2:7][C@@H:6]([CH2:10][N:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[CH2:5]2)[CH2:3][CH2:2]1.C1([O:23][C:24](=O)[NH:25][C:26]2[CH:30]=[C:29]([C:31]([CH3:34])([CH3:33])[CH3:32])[O:28][N:27]=2)C=CC=CC=1.C(N(CC)CC)C>O1CCCC1>[NH3:4].[C:31]([C:29]1[O:28][N:27]=[C:26]([NH:25][C:24]([N:14]2[CH2:15][CH2:16][N:11]([CH2:10][C@@H:6]3[CH2:7][CH2:8][CH2:9][N:4]([CH:1]4[CH2:3][CH2:2]4)[CH2:5]3)[CH2:12][CH2:13]2)=[O:23])[CH:30]=1)([CH3:34])([CH3:32])[CH3:33]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13489605Phenyl 5-tert-butylisoxazol-3-ylcarbamateHCID 598460941-{[(3S)-1-cyclopropylpiperidin-3-yl]methyl}piperazine

Product 2

HCID 222AmmoniaHCID 57656670N-(5-tert-Butylisoxazol-3-yl)-4-{[(3S)-1-cyclopropylpiperidin-3-yl]methyl}piperazine-1-carboxamideYield 105.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-{[(3S)-1-cyclopropylpiperidin-3-yl]methyl}piperazine (60 mg), phenyl(5-tert-butylisoxazol-3-yl)carbamate (84 mg) and triethylamine (54 mg) in tetrahydrofuran (4 mL) was heated to 60° C. in the microwave for 1 hour. The solution was concentrated at reduced pressure and then purified by reverse phase prep HPLC eluting with a mixture of 5-95% acetonitrile in water and then SCX-2 column eluting with methanol then 7M NH3 in methanol to give the title compound as a white solid (55 mg, 52%).

Workup

  1. concentrationThe solution was concentrated at reduced pressure
  2. custompurified by reverse phase prep HPLC
  3. washeluting with a mixture of 5-95% acetonitrile in water
  4. washSCX-2 column eluting with methanol

Sources & evidence

ORD record
ord-f8d74c5f8aec48079f66e767d79f1d44
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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