Diethyl Ether → (2,5-Difluoro-benzyl)-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-6'-yl)-amine hydrochloride salt

HRID 2182165

반응식

HRID 2182165 반응식
C(OC(=O)[N:7]([CH2:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[F:28])[C:8]1[N:13]=[C:12]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:11]=[N:10][CH:9]=1)(C)(C)C.[ClH:30].CCOCC.C(OCC)C>CO.Cl>[ClH:30].[F:28][C:22]1[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=1[CH2:20][NH:7][C:8]1[N:13]=[C:12]([N:14]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19]2)[CH:11]=[N:10][CH:9]=1

참가 물질

6

반응물 3

HCID 3283Diethyl EtherHCID 10953452Ether hydrochloride2회HCID 69730478(2,5-difluoro-benzyl)-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-6'-yl)-carbamic acid tert-butyl ester

생성물 1

HCID 22481974(2,5-Difluoro-benzyl)-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-6'-yl)-amine hydrochloride salt수율 78%

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 887Methanol용매

실험 절차

The general procedure described in Example 4-A was followed using 2,5-difluoro-benzylamine as the amine in the preparation of the first intermediate and DMAP (1 equiv.) to give the BOC-protected compound. The protecting group was removed by dissolving (2,5-difluoro-benzyl)-(3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-6′-yl)-carbamic acid tert-butyl ester (99.6 mg, 0.24 mmol) in methanol (1 mL) and treating it with 1.0M HCl/Ether (3.68 mL, 3.68 mmol) and stirring the reaction mixture overnight at ambient temperature. Additional 1.0M HCl/ether (2 mL) was added to the reaction mixture and stirring continued overnight at room temperature. The reaction was still not complete, therefore conc. HCl (2 drops) was added and the resulting mixture stirred at ambient temperature overnight. Diethyl ether (20 mL) was added to the reaction mixture and stirring continued for 1 h. The solids were filtered from the reaction mixture, washed with Ether, and dried under high vacuum to give the title compound 4-P (64 mg).

후처리

  1. customThe protecting group was removed
  2. stirringstirring continued overnight at room temperature
  3. stirringthe resulting mixture stirred at ambient temperature overnight
  4. stirringstirring
  5. waitcontinued for 1 h
  6. filtrationThe solids were filtered from the reaction mixture
  7. washwashed with Ether
  8. customdried under high vacuum

출처 및 근거

ORD 기록
ord-e5c932272e62468baa401205df97b644
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06894050B2

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