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Sodium Carbonate → N-[1-(4-chlorobenzyl)piperidin-4-yl]-6-chloropyridazin-3-amine

HRID 1429668
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HRID 1429668 반응식
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[Cl:16][C:17]1[N:18]=[N:19][C:20](Cl)=[CH:21][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(N(C)C)=O.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:8][CH2:9][CH:10]([NH:13][C:20]3[N:19]=[N:18][C:17]([Cl:16])=[CH:22][CH:21]=3)[CH2:11][CH2:12]2)=[CH:14][CH:15]=1
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 673313,6-DichloropyridazineHCID 71308331-((4-Chlorophenyl)methyl)piperidin-4-amine

생성물 1

HCID 59805852N-[1-(4-chlorobenzyl)piperidin-4-yl]-6-chloropyridazin-3-amine

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide
용매

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온도
120 °C

실험 절차

A solution of 1-(4-chlorobenzyl)-piperidin-4-yl amine (1 g, 4.45 mmol) (prepared by a procedure similar to that described in WO2001098273), 3,6-dichloropyridazine (670 mg, 4.45 mmol) and sodium carbonate (940 mg, 8.90 mmol) in dimethylacetamide (5 ml) was heated at 120° C. in a microwave reactor (Emrys Optimizer; 0-9 Barr) for 40 minutes. After this period, the reaction mixture was diluted with water and extracted with dichloromethane. The organic layer was dried (MgSO4), filtered and the solvents evaporated in vacuo. Purification by reverse phase HPLC (conditions as previously described) gave E16 (228 mg, 15%). C16H18Cl2N4 requires 336; Found 337 (MH+). 1H NMR (360 MHz, CDCl3) δ1.52 (qd, J=11.5, 3.5 Hz, 2H), 2.08 (d, J=12.5 Hz, 2H), 2.16 (t, J=11.3 Hz, 2H), 2.82 (d, J=11.5 Hz, 2H), 3.48 (s, 2H), 3.77-3.87 (m, 1H), 4.55 (d, J=7.8 Hz, 1H), 6.59 (d, J=9.3 Hz, 1H), 7.14 (d, J=9.3 Hz, 1H), 7.25 (d, J=7.7 Hz, 2H), 7.29 (d, J=7.7 Hz, 2H)

후처리

  1. waitAfter this period
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo
  6. customPurification by reverse phase HPLC (conditions
  7. customgave E16 (228 mg, 15%)

출처 및 근거

ORD 기록
ord-be6bfbf89bd64deaadc901757fb7af05
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08940743B2

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