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

HRID 1432153ノート

反応式

HRID 1432153 の反応式
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

参加物

6

反応物 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 10426DiphosgeneHCID 68942107[2-(4-Cyclopentyl-piperazin-1-yl)-pyridin-4-yl]-methyl-amine hydrochloride2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-82d8c1dbabd340d18749f745a43364ea
出典データセット
uspto-grants-2009_11
特許番号
US07612076B2

反応ノート

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