4-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carboxylic acid → (4-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridin-2-yl)methanol

HRID 1922213ノート

反応式

HRID 1922213 の反応式
[CH:1]1([CH2:7][NH:8][C:9]2[O:10][C:11]3[CH:17]=[C:16]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([C:25](O)=[O:26])[CH:20]=4)[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C1COCC1>[CH:1]1([CH2:7][NH:8][C:9]2[O:10][C:11]3[CH:17]=[C:16]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([CH2:25][OH:26])[CH:20]=4)[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

3

反応物 1

HCID 577255144-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carboxylic acid

生成物 1

HCID 57725588(4-(2-(Cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridin-2-yl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of the 4-(2-(cyclohexylmethylamino)benzo[d]oxazol-6-yloxy)pyridine-2-carboxylic acid (120 mg, 0.33 mmol, 1.0 eq) in 5 mL of THF was added borane-tetrahydrofuran complex (1M, 1 mL, 1 mmol) at 0° C. The reaction mixture was stirred at that temperature for 5 hours. The reaction was quenched with 1M hydrochloric acid. The resulting mixture was extracted with ethyl acetate (2×60 mL). The combined organic layers were washed with water (10 mL), brine (10 mL), then dried over MgSO4, filtered, and evaporated under reduced pressure to give crude product, which was purified by silica gel column eluted with ethyl acetate and hexane to give the titled compound. MH+=354.0.

後処理

  1. customThe reaction was quenched with 1M hydrochloric acid
  2. extractionThe resulting mixture was extracted with ethyl acetate (2×60 mL)
  3. washThe combined organic layers were washed with water (10 mL), brine (10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give crude product, which
  8. customwas purified by silica gel column
  9. washeluted with ethyl acetate and hexane

出典と根拠

ORDレコード
ord-898983447b2447cb88e200edf346982f
出典データセット
uspto-grants-2012_05
特許番号
US08173689B2

反応ノート

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