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

HRID 1094225ノート

反応式

HRID 1094225 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-183924e31bd74b5794c6554e38b0bf6f
出典データセット
uspto-grants-2012_03
特許番号
US08133896B2

反応ノート

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