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

HRID 1756997노트

반응식

HRID 1756997 반응식
[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]

참가 물질

6

반응물 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)

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-3b37f02aa62b44c9bc96f65f48ed277a
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05442064

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