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Sodium Hydroxide → HCID 73386771、化合物

HRID 1480768
ノート
印刷プレビュー

反応式

HRID 1480768 の反応式
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH:14]=O)=[C:9]([O:16][CH3:17])[CH:8]=2)=[CH:5][N:4]=[C:3]1[CH3:18].[H-].[Na+].[CH3:21][N:22]1[CH:26]=[C:25]([C:27]2[C:32]3[N:33]=C(S(C)(=O)=O)[N:35]=[CH:36][C:31]=3[CH:30]=[CH:29][N:28]=2)[CH:24]=[N:23]1.[OH-].[Na+]>C1COCC1.CO>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:35]=[CH:36][C:31]4[CH:30]=[CH:29][N:28]=[C:27]([C:25]5[CH:24]=[N:23][N:22]([CH3:21])[CH:26]=5)[C:32]=4[N:33]=3)=[C:9]([O:16][CH3:17])[CH:8]=2)=[CH:5][N:4]=[C:3]1[CH3:18]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 89996010HCID 89996010、化合物HCID 89996058HCID 89996058、化合物

生成物 1

HCID 73386771HCID 73386771、化合物収率 14%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

A solution of N-(4-(1,2-dimethyl-1H-imidazol-5-yl)-2-methoxyphenyl)formamide (Preparation 55, 37 mg, 0.151 mmol) in THF (1 mL) was treated with sodium hydride (10 mg, 0.250 mmol) at 0° C. After stirring for 20 minutes at room temperature, the mixture was cooled to 0° C. and 8-(1-methyl-1H-pyrazol-4-yl)-2-(methylsulfonyl)pyrido[3,4-d]pyrimidine (Preparation 35, 50 mg, 0.173 mmol) was added. The reaction was allowed to reach room temperature and stirred for 18 hours. Aqueous NaOH (2M, 0.5 mL) and MeOH (0.5 mL) were added and the resulting mixture stirred at room temperature for 1 hour. The volatiles were removed under reduced pressure and the residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with water, brine, dried and evaporated. The residue was purified by silica gel column chromatography eluting with 0 to 10% MeOH in EtOAc to give the title compound (9 mg, 14%).

後処理

  1. temperaturethe mixture was cooled to 0° C.
  2. customto reach room temperature
  3. stirringstirred for 18 hours
  4. stirringthe resulting mixture stirred at room temperature for 1 hour
  5. customThe volatiles were removed under reduced pressure
  6. customthe residue was partitioned between EtOAc and water
  7. extractionThe aqueous layer was extracted with EtOAc
  8. washthe combined organic layers were washed with water, brine
  9. customdried
  10. customevaporated
  11. customThe residue was purified by silica gel column chromatography
  12. washeluting with 0 to 10% MeOH in EtOAc

出典と根拠

ORDレコード
ord-3ebbb98288fb495c9b6d4ea1ff1bda8d
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409907B2

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート