Acetic Acid → 6-chloro-N-[(1S)-1-(3-{[1-(3-methylphenyl)ethyl]amino}phenyl)ethyl]pyrazin-2-amine

HRID 572210

반응식

HRID 572210 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH3:9])[CH:5]=N[CH:7]=1.[NH2:11][C:12]1[CH:13]=[C:14]([C@@H:18]([NH:20][C:21]2[CH:26]=[N:25][CH:24]=[C:23]([Cl:27])[N:22]=2)[CH3:19])[CH:15]=[CH:16][CH:17]=1.[C:28](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.Cl>ClCCCl>[Cl:27][C:23]1[N:22]=[C:21]([NH:20][C@H:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([NH:11][CH:5]([C:4]3[CH:8]=[CH:9][CH:7]=[C:2]([CH3:1])[CH:3]=3)[CH3:28])[CH:13]=2)[CH3:19])[CH:26]=[N:25][CH:24]=1

참가 물질

7

반응물 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 5775691-(5-Methylpyridin-3-yl)ethan-1-oneHCID 5049666Sodium triacetoxyborohydrideHCID 25218447(S)-N-(1-(3-aminophenyl)ethyl)-6-chloropyrazin-2-amine

생성물 1

HCID 875330326-chloro-N-[(1S)-1-(3-{[1-(3-methylphenyl)ethyl]amino}phenyl)ethyl]pyrazin-2-amine수율 14.2%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
80 °C

실험 절차

To a solution of 1-(5-methylpyridin-3-yl)ethanone (135 mg, 1 mmol) and N-[(1S)-1-(3-aminophenyl)ethyl]-6-chloropyrazin-2-amine (248 mg, 1 mmol) in 1,2-dichloroethane (5 mL) was added sodium triacetoxyborohydride (300 mg, 1.4 mmol), in one portion, and glacial acetic acid (0.18 mL, 3 mmol). The mixture was heated in the microwave reactor at 80° C. for 1 hour. After this time the mixture was stirred with dilute aqueous hydrochloric acid (2M, 7 mL) for 15 minutes and the two phases were separated. The aqueous phase was basified to pH 9 with solid potassium hydroxide and was extracted with dichloromethane (2×20 mL). The extracts were washed with brine (20 mL), dried (MgSO4) and concentrated under reduced pressure to give an orange oil which was purified by flash chromatography (silica, ethyl acetate/methanol) to give 6-chloro-N-[(1S)-1-(3-{[1-(3-methylphenyl)ethyl]amino}phenyl)ethyl]pyrazin-2-amine (52 mg, 14%) as a pale yellow oil.

후처리

  1. customthe two phases were separated
  2. extractionwas extracted with dichloromethane (2×20 mL)
  3. washThe extracts were washed with brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give an orange oil which
  7. customwas purified by flash chromatography (silica, ethyl acetate/methanol)

출처 및 근거

ORD 기록
ord-0be33a69c4534afe957e0d5d4eb4bbc3
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029386B2

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