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

HRID 731408
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HRID 731408 반응식
[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]
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참가 물질

10

반응물 7

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1643087c39924873b3b954fe40406b26
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07582769B2

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