Diisopropylethylamine → HCID 86618929、化合物

HRID 1094230ノート

反応式

HRID 1094230 の反応式
C(N(C(C)C)CC)(C)C.[CH:10]1([C:13]2[N:18]=[C:17]([Cl:19])[C:16]([CH3:20])=[C:15](Cl)[N:14]=2)[CH2:12][CH2:11]1.[NH:22]1[CH2:27][CH2:26][CH:25]([C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[N:31][CH:32]=[CH:33][CH:34]=3)[N:29]=2)[CH2:24][CH2:23]1.N1C2C(=CC=CN=2)C=CC=1.C(=O)(O)[O-].[Na+]>O.C(OCC)(=O)C.CC(N(C)C)=O>[CH:10]1([C:13]2[N:14]=[C:15]([N:22]3[CH2:23][CH2:24][CH:25]([C:28]4[CH:37]=[CH:36][C:35]5[C:30](=[N:31][CH:32]=[CH:33][CH:34]=5)[N:29]=4)[CH2:26][CH2:27]3)[C:16]([CH3:20])=[C:17]([Cl:19])[N:18]=2)[CH2:11][CH2:12]1

参加物

9

反応物 5

HCID 81531DiisopropylethylamineHCID 1360691,8-NaphthyridineHCID 516892Sodium BicarbonateHCID 545957314,6-Dichloro-2-cyclopropyl-5-methylpyrimidineHCID 666409192-(Piperidin-4-YL)-1,8-naphthyridine

生成物 1

HCID 86618929HCID 86618929、化合物収率 51.7%

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
100 °C

実験手順

20 ml of dimethylacetamide and 3.36 ml (19.2 mmoles) of diisopropylethylamine are added into a single-necked flask containing 1.5 g (7.39 mmoles) of 2-cyclopropyl-4,6-dichloro-5-methyl-pyrimidine and 1.58 g (7.39 mmoles) of 2-piperidin-4-yl-[1,8]naphthyridine. This mixture is heated at 100° C. overnight. The next day 0.2 equivalent of naphthyridine is added and the reaction mixture is heated for another 6 hours, followed by returning to ambient temperature before concentration to dryness. 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 (50-50) to 100% ethyl acetate. 1.45 g of expected product is obtained.

後処理

  1. temperaturethe reaction mixture is heated for another 6 hours
  2. concentrationby returning to ambient temperature before concentration to dryness
  3. customThe residue obtained
  4. customThe organic phase is separated
  5. dry with materialThe collected organic phases are dried over magnesium sulphate
  6. customthe solvent is evaporated off under reduced pressure (2 kPa)
  7. customThe residue is chromatographed on silica gel eluting with a gradient of heptane-ethyl acetate (50-50) to 100% ethyl acetate

出典と根拠

ORDレコード
ord-64013a6b865a4078997bd59c9f044f8b
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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