Urea → N-(1-Acetylpiperidin-4-yl)-N-cyclopentyl-N'-1,3-thiazol-2-ylurea

HRID 731408Notes

Reaction equation

HRID 731408 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=O)(=[O:3])[CH3:2].C1(N)CCCC1.C([BH3-])#N.[Na+].NC(N)=O.[CH:25]1([N:30](C2CCCC2)[C:31]([NH:33][C:34]2[S:35][CH:36]=[CH:37][N:38]=2)=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26]1.C(=C1N=CC=N1)=O.NC1SC=CN=1>C1COCC1.CO>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([N:30]([CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29]2)[C:31]([NH:33][C:34]2[S:35][CH:36]=[CH:37][N:38]=2)=[O:32])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

10

Reactant 7

HCID 1176UreaHCID 21552-AminothiazoleHCID 2906CyclopentylamineHCID 5003444Sodium cyanoborohydrideHCID 118159051-Acetylpiperidin-2-oneHCID 13571086CarbonylimidazoleHCID 57688319N,N-Dicyclopentyl-N'-1,3-thiazol-2-ylurea

Product 1

HCID 57688263N-(1-Acetylpiperidin-4-yl)-N-cyclopentyl-N'-1,3-thiazol-2-ylurea

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepared according to general procedure (I). To a mixture of N-acetyl-piperidone (1.4 g) and cyclopentylamine (0.9 g) and molecular sieves (5 g) in THF (8 mL) and methanol (8 mL) was added sodium cyanoborohydride (2.1 g) and the reaction was stirred overnight at room temperature. Insoluble material was removed by filtration and after removal of solvent in vacuo the crude secondary amine (0.57 g) was isolated. The urea coupling was performed in an similar manner to the synthesis of 1,1-dicyclopentyl-3-thiazol-2-yl-urea using carbonyl imidazole and 2-aminothiazole as starting material.

Workup

  1. customPrepared
  2. customInsoluble material was removed by filtration
  3. customafter removal of solvent in vacuo the crude secondary amine (0.57 g)
  4. customwas isolated

Sources & evidence

ORD record
ord-1643087c39924873b3b954fe40406b26
Source dataset
uspto-grants-2009_09
Patent number
US07582769B2

Reaction notes

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