(2-(4-Methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamine → 1-(6,7-dihydro-5H-cyclopenta[b]pyridin-3-yl)-3-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)urea

HRID 571980노트

반응식

HRID 571980 반응식
[N:1]1[CH:6]=[C:5]([NH:7][C:8](=[O:16])OC2C=CC=CC=2)[CH:4]=[C:3]2[CH2:17][CH2:18][CH2:19][C:2]=12.[CH3:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]2[C:32]([CH2:33][NH2:34])=[CH:31][CH:30]=[C:29]([C:35]([F:38])([F:37])[F:36])[N:28]=2)[CH2:23][CH2:22]1>CN(C=O)C.CN(C1C=CN=CC=1)C>[N:1]1[CH:6]=[C:5]([NH:7][C:8]([NH:34][CH2:33][C:32]2[C:27]([N:24]3[CH2:25][CH2:26][CH:21]([CH3:20])[CH2:22][CH2:23]3)=[N:28][C:29]([C:35]([F:38])([F:36])[F:37])=[CH:30][CH:31]=2)=[O:16])[CH:4]=[C:3]2[CH2:17][CH2:18][CH2:19][C:2]=12

참가 물질

5

반응물 2

HCID 58873687(2-(4-Methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamineHCID 86676321phenyl 6,7-dihydro-5H-cyclopenta[b]pyridin-3-ylcarbamate

생성물 1

HCID 712369681-(6,7-dihydro-5H-cyclopenta[b]pyridin-3-yl)-3-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)urea수율 77.4%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

To a solution of phenyl 6,7-dihydro-5H-cyclopenta[b]pyridin-3-ylcarbamate (E) (80 mg, 0.31 mmol) in DMF was added DMAP (38 mg, 0.31 mmol) and (2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methanamine (F) (90 mg, 0.33 mmol) at room temperature. The reaction mixture was heated to 50° C. for 14 h. TLC showed complete consumption of starting material. The reaction mixture was diluted with water and extracted with EtOAc. The organic part was washed with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude was purified by column chromatography to give pure 1-(6,7-dihydro-5H-cyclopenta[b]pyridin-3-yl)-3-((2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)pyridin-3-yl)methyl)urea (example compound I) (104 mg, 76%).

후처리

  1. customconsumption of starting material
  2. additionThe reaction mixture was diluted with water
  3. extractionextracted with EtOAc
  4. washThe organic part was washed with water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by column chromatography

출처 및 근거

ORD 기록
ord-836fbcd10b794bceac3ff41740125201
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029378B2

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