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Diisopropylethylamine → 5-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (1-ethyl-1-hydroxymethyl-propyl)-amide

HRID 1480110
ノート
印刷プレビュー

反応式

HRID 1480110 の反応式
[CH:1]1([C:4]2[C:5]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[CH:6][C:7]([C:10]([OH:12])=O)=[N:8][CH:9]=2)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:52][C:53]([CH2:58][CH3:59])([CH2:56][CH3:57])[CH2:54][OH:55].C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH2:56]([C:53]([NH:52][C:10]([C:7]1[CH:6]=[C:5]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:4]([CH:1]2[CH2:2][CH2:3]2)=[CH:9][N:8]=1)=[O:12])([CH2:54][OH:55])[CH2:58][CH3:59])[CH3:57]
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 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 143256072-Amino-2-ethylbutan-1-olHCID 902036745-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid

生成物 1

HCID 90214935
5-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (1-ethyl-1-hydroxymethyl-propyl)-amide
収率 58%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-Cyclopropyl-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid (Example 48c, 20 mg, 77 μmol) in DMF (1.5 mL) was added HATU (32 mg, 84 μmol) and DIPEA (15 μl, 84 μmol). The reaction mixture was stirred at roomtemperature for 20 minutes followed by addition of 2-amino-2-ethylbutan-1-ol (CAN 19792-52-0, 10 mg, 84 μmol). The reaction was stirred at room temperature overnight and was poured into 15 mL of a saturated aqueous solution of sodium bicarbonate. The solution was extracted three times with 10 mL dichloromethane. The organic phases were combined, dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica, eluting with a heptane/ethylacetate gradient to yield the titled compound (16 mg, 58%) as white solid. MS (ESI, m/z): 361.1 (M+H+).

後処理

  1. stirringThe reaction was stirred at room temperature overnight
  2. extractionThe solution was extracted three times with 10 mL dichloromethane
  3. dry with materialdried over sodium sulfate
  4. customevaporated down to dryness
  5. customThe crude material was purified by flash chromatography on silica
  6. washeluting with a heptane/ethylacetate gradient

出典と根拠

ORDレコード
ord-00a3cd1ccf75476b897a7fc86be628dc
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409866B2

反応ノート

読み込み中…

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