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Dimethylbarbituric acid → N-(((2S,3R)-3-Methylpiperidin-2-yl)methyl)-5-(trifluoromethyl)pyridin-2-amine

HRID 60902
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인쇄 미리보기

반응식

HRID 60902 반응식
[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4](C(OCC=C)=O)[C@@H:3]1[CH2:14][NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=1.CN1C(=O)CC(=O)N(C)C1=O>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][NH:4][C@@H:3]1[CH2:14][NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:18][N:17]=1
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참가 물질

5

반응물 2

HCID 69860Dimethylbarbituric acidHCID 89748220(2S,3R)-Allyl 3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidine-1-carboxylate

생성물 1

HCID 89739447N-(((2S,3R)-3-Methylpiperidin-2-yl)methyl)-5-(trifluoromethyl)pyridin-2-amine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6344
Dichloromethane
용매

실험 절차

A mixture of (2S,3R)-allyl 3-methyl-2-(((5-(trifluoromethyl)pyridin-2-yl)amino)methyl)piperidine-1-carboxylate (0.528 g, 1.48 mmol), Pd(PPh3)4 (0.086 g, 0.0074 mmol) and 1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione (0.14 g, 0.89 mmol) in DCM (20 mL) was stirred at rt. When the starting material was consumed as judged by reverse-phase HPLC analysis, the reaction was concentrated in vacuo. The crude residue was taken up in EtOAc, and washed with satd. aq. NaHCO3, brine, dried (MgSO4), and concentrated to obtain the crude which was purified by silica gel (0˜100% DCM/EtOAc) to afford the title compound. ESI-MS (m/z): 274 [M+1]+.

후처리

  1. customWhen the starting material was consumed
  2. concentrationthe reaction was concentrated in vacuo
  3. washwashed with satd
  4. dry with materialaq. NaHCO3, brine, dried (MgSO4)
  5. concentrationconcentrated
  6. customto obtain the crude which
  7. customwas purified by silica gel (0˜100% DCM/EtOAc)

출처 및 근거

ORD 기록
ord-4075ba61013643928e15f440f765ce6f
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09440982B2

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