2-Methoxyethanol → HCID 178496145、化合物

HRID 518689ノート

反応式

HRID 518689 の反応式
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[C:9]1[CH:14]=[C:13]([NH:15][C@@H:16]2[CH2:21][CH2:20][C@H:19]([C:22]([NH:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[C:12]([N+:28]([O-:30])=[O:29])=[CH:11][N:10]=1>C1COCC1>[CH:25]([NH:24][C:22]([C@H:19]1[CH2:20][CH2:21][C@@H:16]([NH:15][C:13]2[C:12]([N+:28]([O-:30])=[O:29])=[CH:11][N:10]=[C:9]([O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:14]=2)[CH2:17][CH2:18]1)=[O:23])([CH3:27])[CH3:26]

参加物

5

反応物 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 178457831HCID 178457831、化合物

生成物 1

HCID 178496145HCID 178496145、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To an ice-bath cooled solution of 2-methoxyethanol (0.296 mL, 3.76 mmol) in THF (2.3 mL) was added sodium hydride (150 mg, 3.76 mmol), and the mixture was stirred for 20 minutes. To the mixture was added cis-4-(2-chloro-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide (400 mg, 1.174 mmol), and the flask was removed from the ice bath and the reaction was stirred for 2 hours. The reaction was quenched with water and diluted with DCM, washed with water, saturated aqueous NaHCO3, and the organic layer dried over Na2SO4 and filtered through Celite® brand filter aid. The material was purified via flash chromatography using a linear gradient of 0% to 5% of 1% NH4OH in MeOH in CH2Cl2. The title compound was collected as a yellow solid (273 mg, 61% yield).

後処理

  1. customthe flask was removed from the ice bath
  2. stirringthe reaction was stirred for 2 hours
  3. customThe reaction was quenched with water
  4. additiondiluted with DCM
  5. washwashed with water, saturated aqueous NaHCO3
  6. dry with materialthe organic layer dried over Na2SO4
  7. filtrationfiltered through Celite® brand
  8. filtrationfilter aid
  9. customThe material was purified via flash chromatography

出典と根拠

ORDレコード
ord-bae4857bdfb74c88bd301c7c4c41f6dc
出典データセット
uspto-grants-2015_08
特許番号
US09115127B2

反応ノート

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