Hydrochloric Acid → HCID 10158751、化合物

HRID 354139ノート

反応式

HRID 354139 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([N:12]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[O:11])=[CH:5][CH:4]=1.[CH:27](Br)([CH3:29])[CH3:28].CCN(C(C)C)C(C)C.C(=O)([O-])O.[Na+].Cl>C(#N)C.C(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([N:12]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)[CH:13]2[CH2:18][CH2:17][N:16]([CH:27]([CH3:29])[CH3:28])[CH2:15][CH2:14]2)=[O:11])=[CH:7][CH:8]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 63582-BromopropaneHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 10270645HCID 10270645、化合物

生成物 1

HCID 10158751HCID 10158751、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
60 °C

実験手順

42ELH89 (0.25 g, 0.67 mmol, 1.0 eq) was transferred to a 4 ml vial and dissolved in acetonitrile (2 ml). Isopropyl bromide (0.25 g, 3.0 eq.) was added along with Hünigs base (0.87 g, 10.0 eq.). The vial was sealed and shaken for 4 days at 60° C. The reaction mixture was transferred to a separatory funnel with distilled water and CH2Cl2. The aqueous phase was made basic with sodium hydrogen carbonate and extracted with dichloromethane (3 times). The organic layers were collected and dried with sodium sulfate and concentrated, this resulted in a yellow oil. The product was purified by flash chromatography (3% MeOH in CH2Cl2). The resulting product was dissolved in dichloromethane (1 ml) and HCl (1 eq. 2 M HCl in ether) was added under stirring. The salt precipitated by addition of the dichloromethane solution into heptane. Concentration on the rotary evaporator returned the product as white crystals. Yield 101.2 mg (63%), UV/MS 94/96 (M+ 415), Rf 0.25 (3% MeOH/CH2Cl2).

後処理

  1. customThe vial was sealed
  2. extractionextracted with dichloromethane (3 times)
  3. customThe organic layers were collected
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customthis resulted in a yellow oil
  7. customThe product was purified by flash chromatography (3% MeOH in CH2Cl2)
  8. dissolutionThe resulting product was dissolved in dichloromethane (1 ml)
  9. stirringunder stirring
  10. customThe salt precipitated by addition of the dichloromethane solution into heptane
  11. concentrationConcentration
  12. customon the rotary evaporator

出典と根拠

ORDレコード
ord-30ccfbca50944918817bbbc8be836028
出典データセット
uspto-grants-2004_06
特許番号
US06756393B2

反応ノート

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