Diisopropylethylamine → 2-[1-(6-Chloro-5-methoxy-2-methyl-pyrimidin-4-yl)-piperidin-4-yl]-[1,8]naphthyridine

HRID 1094225

반응식

HRID 1094225 반응식
Cl[C:2]1[C:7]([O:8][CH3:9])=[C:6]([Cl:10])[N:5]=[C:4]([CH3:11])[N:3]=1.C(N(C(C)C)CC)(C)C.[NH:21]1[CH2:26][CH2:25][CH:24]([C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[N:30][CH:31]=[CH:32][CH:33]=3)[N:28]=2)[CH2:23][CH2:22]1.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C.CC(N(C)C)=O>[Cl:10][C:6]1[N:5]=[C:4]([CH3:11])[N:3]=[C:2]([N:21]2[CH2:22][CH2:23][CH:24]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[N:30][CH:31]=[CH:32][CH:33]=4)[N:28]=3)[CH2:25][CH2:26]2)[C:7]=1[O:8][CH3:9]

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 582936514,6-dichloro-5-methoxy-2-methylPyrimidineHCID 666409192-(Piperidin-4-YL)-1,8-naphthyridine

생성물 1

HCID 866189262-[1-(6-Chloro-5-methoxy-2-methyl-pyrimidin-4-yl)-piperidin-4-yl]-[1,8]naphthyridine수율 50.5%

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

반응 조건

온도
120 °C

실험 절차

30 ml of dimethylacetamide, 0.9 g (4.66 mmoles) 4,6-dichloro-2-methyl-5-methoxy-pyrimidine and 3 ml of diisopropylethylamine are added into a single-necked flask containing 1.1 g (5.2 mmoles) of 2-piperidin-4-yl-[1,8]naphthyridine. This mixture is heated at 120° C. for 4 hours then concentrated to dryness under reduced pressure (2 kPa). The residue obtained is taken up in a mixture of water, ethyl acetate and a saturated solution of sodium bicarbonate. The organic phase is separated and the aqueous phase reextracted with ethyl acetate. The collected organic phases are dried over magnesium sulphate then the solvent is evaporated off under reduced pressure (2 kPa). The residue is chromatographed on silica gel eluting with a gradient of heptane-ethyl acetate of 100-0 to 0-100. 870 mg of expected product is obtained in the form of a yellow solid.

후처리

  1. concentrationthen concentrated to dryness under reduced pressure (2 kPa)
  2. customThe residue obtained
  3. customThe organic phase is separated
  4. dry with materialThe collected organic phases are dried over magnesium sulphate
  5. customthe solvent is evaporated off under reduced pressure (2 kPa)
  6. customThe residue is chromatographed on silica gel eluting with a gradient of heptane-ethyl acetate of 100-0 to 0-100

출처 및 근거

ORD 기록
ord-183924e31bd74b5794c6554e38b0bf6f
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133896B2

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