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

HRID 60902

反応式

HRID 60902 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-4075ba61013643928e15f440f765ce6f
出典データセット
uspto-grants-2016_09
特許番号
US09440982B2

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