Triethylamine → 1-(5-Cyanopyrid-2-yl)-4-[4-(methoxycarbonylmethyl)-piperidinocarbonyl]-piperidine

HRID 1756997ノート

反応式

HRID 1756997 の反応式
[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][N:11]=2)[CH2:6][CH2:5]1)([OH:3])=O.Cl.[NH:19]1[CH2:24][CH2:23][CH:22]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:21][CH2:20]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O>[C:16]([C:13]1[CH:14]=[CH:15][C:10]([N:7]2[CH2:8][CH2:9][CH:4]([C:1]([N:19]3[CH2:24][CH2:23][CH:22]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH2:21][CH2:20]3)=[O:3])[CH2:5][CH2:6]2)=[N:11][CH:12]=1)#[N:17]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 162274741-(5-Cyano-2-pyridinyl)-4-piperidinecarboxylic acidHCID 18423605Methyl (piperidin-4-yl)acetate--hydrogen chloride (1/1)

生成物 1

HCID 193915041-(5-Cyanopyrid-2-yl)-4-[4-(methoxycarbonylmethyl)-piperidinocarbonyl]-piperidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2.3 g of 4-carboxy-1-(5-cyanopyrid-2-yl)-piperidine, 2.0 g of methyl 4-piperidylacetate hydrochloride, 4.8 g of 2-[(1H)-benzotriazol-1-yl]-1,1,3,3-tetramethyl-uronium tetrafluoroborate and 5 ml of triethylamine in 75 ml of dimethylformamide is stirred at ambient temperature for 16 hours. The solvent is removed under reduced pressure. The residue is diluted with water and the aqueous phase is extracted with ethyl acetate. The organic phase is washed with water and saturated saline solution and dried over sodium sulphate. The solvent is removed under reduced pressure and the residue is chromatographed over silica gel. Yield: 2.75 g (74% of theory), Melting point: 112°-115° C. Rf value: 0.40 (silica gel; methylene chloride/methanol=15:1)

後処理

  1. customThe solvent is removed under reduced pressure
  2. additionThe residue is diluted with water
  3. extractionthe aqueous phase is extracted with ethyl acetate
  4. washThe organic phase is washed with water and saturated saline solution
  5. dry with materialdried over sodium sulphate
  6. customThe solvent is removed under reduced pressure
  7. customthe residue is chromatographed over silica gel

出典と根拠

ORDレコード
ord-3b37f02aa62b44c9bc96f65f48ed277a
出典データセット
uspto-grants-1995_08
特許番号
US05442064

反応ノート

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