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Triethylamine → 4-(3-(5-cyclopropylpyridin-2-yloxy)benzylidene)-N-(pyridin-3-yl)piperidine-1-carboxamide

HRID 1666385
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HRID 1666385 반응식
FC(F)(F)C(O)=O.[CH:8]1([C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]=[C:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[CH:19]=3)=[N:15][CH:16]=2)[CH2:10][CH2:9]1.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([NH:37][C:38](=O)[O:39]C2C=CC=CC=2)[CH:32]=1.C(N(CC)CC)C>CS(C)=O>[CH:8]1([C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]3[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=3)[CH:24]=[C:25]3[CH2:30][CH2:29][N:28]([C:38]([NH:37][C:33]4[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=4)=[O:39])[CH2:27][CH2:26]3)=[N:15][CH:16]=2)[CH2:10][CH2:9]1
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 6935890Phenyl pyridin-3-ylcarbamateHCID 668761235-Cyclopropyl-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine trifluoroacetate

생성물 1

HCID 249640604-(3-(5-cyclopropylpyridin-2-yloxy)benzylidene)-N-(pyridin-3-yl)piperidine-1-carboxamide수율 58%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide
용매

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온도
60 °C

실험 절차

To a solution of 5-cyclopropyl-2-(3-(piperidin-4-ylidenemethyl)phenoxy)pyridine trifluoroacetate (125 mg, 0.408 mmol) in DMSO (5 mL) was added phenyl pyridin-3-ylcarbamate (87.4 mg, 0.408 mmol) followed by triethylamine (0.12 mL, 0.82 mmol). The reaction was heated to 60° C. overnight and then allowed to cool to RT. The reaction mixture was partitioned between EtOAc and water. The organic layer was dried and concentrated. Purification by silica gel column chromatography (0-5% MeOH/CH2Cl2) afforded the title compound as a white foam (101 mg, 58% yield). MS (APCI 10V) AP+2 427.07; 1H NMR (400 MHz, CDCl3) δ ppm 0.61-0.66 (m, 2H) 0.93-0.99 (m, 2H) 1.55 (s, 1H) 1.81-1.89 (m, 1H) 2.45 (t, 2H) 2.58 (t, 2H) 3.50 (t, 2H) 3.60 (t, 2H) 6.38 (s, 1H) 6.44 (s, 1H) 6.80 (d, 1H) 6.94 (br. s., 1H) 6.96-7.01 (m, 2H) 7.20-7.23 (m, 1H) 7.29-7.35 (m, 2H) 7.99-8.01 (m, 1H) 8.26 (d, 1H) 8.42 (d, 1H).

후처리

  1. temperatureto cool to RT
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customPurification by silica gel column chromatography (0-5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-4b2e27eebfde4dcf8147abd79e9286b2
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08044052B2

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