Triethylamine → 5-[4-(7-Methoxy-3-phenyl-imidazo[1,2-a]pyrimidin-2-yl)-phenyl]-2-oxa-4-aza-bicyclo[3.1.1]heptan-3-one

HRID 872300

反応式

HRID 872300 の反応式
Br[CH:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]23[CH2:17][CH:15]([CH2:16]2)[O:14][C:13](=[O:18])[NH:12]3)=[CH:7][CH:6]=1)=O.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][N:30]=[C:29]([NH2:33])[N:28]=1.C(N(CC)CC)C>C(O)C>[CH3:25][O:26][C:27]1[CH:32]=[CH:31][N:30]2[C:2]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([C:11]45[CH2:17][CH:15]([CH2:16]4)[O:14][C:13](=[O:18])[NH:12]5)=[CH:7][CH:6]=3)[N:33]=[C:29]2[N:28]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 674284-Methoxy-2-pyrimidinamineHCID 866910395-[4-(2-Bromo-2-phenyl-acetyl)-phenyl]-2-oxa-4-aza-bicyclo[3.1.1]heptan-3-one

生成物 1

HCID 666651185-[4-(7-Methoxy-3-phenyl-imidazo[1,2-a]pyrimidin-2-yl)-phenyl]-2-oxa-4-aza-bicyclo[3.1.1]heptan-3-one

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
100 °C

実験手順

A mixture of crude 5-[4-(2-bromo-2-phenyl-acetyl)-phenyl]-2-oxa-4-aza-bicyclo[3.1.1]heptan-3-one (2.5 g), 4-methoxypyrimidin-2-amine (1.26 g), triethylamine (0.84 mL) and ethanol (62 mL), under argon, was heated at 100° C. (bath temperature) for 6 hours. On cooling the reaction was concentrated and partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc and the combined organic phases were washed with brine, dried and concentrated. Purification was achieved by chromatography on silica gel followed by preparative reverse phase HPLC to give the title compound.

後処理

  1. temperatureOn cooling the reaction
  2. concentrationwas concentrated
  3. custompartitioned between EtOAc and water
  4. extractionThe aqueous phase was extracted with EtOAc
  5. washthe combined organic phases were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customPurification

出典と根拠

ORDレコード
ord-b35483ed864f417a9415f319200dab38
出典データセット
uspto-grants-2015_03
特許番号
US08975265B2

関連ノート

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