Piperidine → Piperidine-1-carboxylic acid [2-(4-cyclopentyl-piperazin-1-yl)-pyridin-4-yl]-methyl-amide

HRID 272541노트

반응식

HRID 272541 반응식
Cl.[CH:2]1([N:7]2[CH2:12][CH2:11][N:10]([C:13]3[CH:18]=[C:17]([NH:19][CH3:20])[CH:16]=[CH:15][N:14]=3)[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.O=C(Cl)[O:23][C:24](Cl)(Cl)Cl.CCN(CC)CC.[NH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>C1COCC1>[CH:2]1([N:7]2[CH2:8][CH2:9][N:10]([C:13]3[CH:18]=[C:17]([N:19]([CH3:20])[C:24]([N:36]4[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]4)=[O:23])[CH:16]=[CH:15][N:14]=3)[CH2:11][CH2:12]2)[CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

6

반응물 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 10426DiphosgeneHCID 68942107[2-(4-Cyclopentyl-piperazin-1-yl)-pyridin-4-yl]-methyl-amine hydrochloride2회

생성물 1

HCID 11689259Piperidine-1-carboxylic acid [2-(4-cyclopentyl-piperazin-1-yl)-pyridin-4-yl]-methyl-amide수율 52%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 20 mg (0.08 mmol) [2-(4-cyclopentyl-piperazin-1-yl)-pyridin-4-yl]-methyl-amine hydrochloride (intermediate 10), 46 mg (0.08 mmol) diphosgene and 31 mg (0.3 mmol) NEt3 in 1 ml THF was treated with 43 mg (0.5 mmol) piperidine (commercially available) and stirred for 30 min at room temperature. After evaporation of all volatiles the residue was taken up in methanol/DMF and subjected to preparative HPLC purification on reversed phase eluting with a gradient of acetonitrile/water (0.05% triethylamine). The combined product fractions were evaporated to dryness to yield 15 mg (52%) of the title compound as white solid. MS(m/e): 372.1 (MH+; 100%).

후처리

  1. customAfter evaporation of all volatiles the residue
  2. customsubjected to preparative HPLC purification on reversed phase
  3. washeluting with a gradient of acetonitrile/water (0.05% triethylamine)
  4. customThe combined product fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-b24bbf12078e45dca1489fb5cf28cd8a
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456175B2

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