Pentane, 1-isocyanato- → 4-[4-(4,5-dihydro-5-phenyl-3-isoxazoly)-2-thiazolyl]-N-pentyl-1-piperidinecarboxamide

HRID 1802322Notes

Reaction equation

HRID 1802322 reaction equation
[C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12]3[N:13]=[C:14]([CH:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[S:15][CH:16]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23]([N:28]=[C:29]=[O:30])[CH2:24][CH2:25][CH2:26][CH3:27]>ClCCl.C(OCC)C>[C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12]3[N:13]=[C:14]([CH:17]4[CH2:22][CH2:21][N:20]([C:29]([NH:28][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:30])[CH2:19][CH2:18]4)[S:15][CH:16]=3)[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 206036Pentane, 1-isocyanato-HCID 666184764-[4-(4,5-Dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]piperidine2×

Product 1

HCID 666286224-[4-(4,5-dihydro-5-phenyl-3-isoxazoly)-2-thiazolyl]-N-pentyl-1-piperidinecarboxamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]piperidine (i.e. the product of Example 1, Step B) (0.10 g, 0.32 mmol) and pentyl isocyanate (0.036 g, 0.32 mmol) in dichloromethane (10 mL) was stirred at room temperature overnight, then filtered and concentrated under reduced pressure to provide a white solid. The solid was slurried in diethyl ether, filtered and air-dried to provide the title compound, a compound of the present invention, as a white powder (0.081 g), melting at 132-134° C.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customto provide a white solid
  4. filtrationfiltered
  5. customair-dried

Sources & evidence

ORD record
ord-3d6fd28d0d934dad9f9fc0afda4f37c9
Source dataset
uspto-grants-2013_01
Patent number
US08349870B2

Reaction notes

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