Hydrochloric Acid → 6-[(1,1-Dimethylethyl)thio]-3-pyridinemethanamine

HRID 911645노트

반응식

HRID 911645 반응식
[C:1]([S:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].Cl>C1COCC1.CO>[NH2:11][CH2:10][C:9]1[CH:12]=[CH:13][C:6]([S:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[N:7][CH:8]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 284131906-(Tert-butylsulfanyl)pyridine-3-carbonitrile

생성물 1

HCID 435287746-[(1,1-Dimethylethyl)thio]-3-pyridinemethanamine수율 61.5%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매2회

실험 절차

Use a method similar to the General Procedure 6-5 to react 6-(tert-butylthio)nicotinonitrile (4.4 g, 22.7 mmol) in anhydrous THF (25 mL) with 1M BH3-THF complex in THF (25 mL, 25 mmol). Add 5M aqueous HCl (10 mL) cautiously and stir the mixture overnight at room temperature. Extract into EtOAc, wash with brine, dry over MgSO4 and concentrate in vacuo to give an orange solid. Dissolve the crude mixture in methanol and filter through an SCX column eluting with methanol followed by 3M ammonia in methanol to obtain the title compound (2.74 g, 61%). MS (ES+) m/z: 197 (M+H)+.

후처리

  1. extractionExtract into EtOAc
  2. washwash with brine
  3. dry with materialdry over MgSO4
  4. concentrationconcentrate in vacuo
  5. customto give an orange solid
  6. filtrationfilter through an SCX column
  7. washeluting with methanol

출처 및 근거

ORD 기록
ord-69df268f146a47289309304c78373329
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022062B2

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