Hydrochloric Acid → HCID 10158751, 화합물

HRID 354139노트

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HRID 354139 반응식
[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

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 63582-BromopropaneHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 10270645HCID 10270645, 화합물

생성물 1

HCID 10158751HCID 10158751, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

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온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-30ccfbca50944918817bbbc8be836028
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756393B2

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