Hydrochloric Acid → HCID 59536664, 화합물

HRID 1922176노트

반응식

HRID 1922176 반응식
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([CH:13]([O:18][C:19]2[C:20]([CH3:27])=[N:21][C:22]([NH:25][CH3:26])=[CH:23][CH:24]=2)[CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:9]1)=O)(C)(C)C.Cl>>[CH3:27][C:20]1[C:19]([O:18][CH:13]([C@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:24][CH:23]=[C:22]([NH:25][CH3:26])[N:21]=1

참가 물질

3

반응물 2

HCID 313Hydrochloric AcidHCID 66737795HCID 66737795, 화합물

생성물 1

HCID 59536664HCID 59536664, 화합물수율 12%

실험 절차

Stir a mixture of (3S)-3-[1-(2-methyl-6-methylamino-3-pyridyloxy)-3-methyl-butyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (S-2) and aqueous HCl (4M, 0.261 mL, 1.04 mmol) at room temperature for 1 hour. After full conversion, concentrate the mixture, dissolve in dichloromethane and load the mixture onto a pre-packed SCX column. Wash with dichloromethane followed by methanol. Release the product with 2M NH3 in methanol and concentrate under reduced pressure. Purify the crude residue by reverse phase chromatography (17-43% gradient actonitrile in 0.01 M ammoniumformate in water, 85 mL/min, for 8 min., C18 ODB XBridge column, 30×75 mm, 5 μm) to give 9 mg (12%) of (3S)-3-[1-(2-methyl-6-methylamino-3-pyridyloxy)-3-methyl-butyl]-pyrrolidine (S-2). MS (m/z)=278 [M+1].

후처리

  1. concentrationAfter full conversion, concentrate the mixture
  2. dissolutiondissolve in dichloromethane
  3. washWash with dichloromethane
  4. concentrationconcentrate under reduced pressure
  5. customPurify the crude residue by reverse phase chromatography (17-43% gradient actonitrile in 0.01 M ammoniumformate in water, 85 mL/min, for 8 min., C18 ODB XBridge column, 30×75 mm, 5 μm)

출처 및 근거

ORD 기록
ord-6c61291de4464440a039ad67976ef330
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173821B2

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