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

HRID 2182165

反応式

HRID 2182165 の反応式
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

参加物

6

反応物 3

HCID 3283Diethyl EtherHCID 10953452Ether hydrochloride2 回HCID 69730478(2,5-difluoro-benzyl)-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-6'-yl)-carbamic acid tert-butyl ester

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid触媒HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e5c932272e62468baa401205df97b644
出典データセット
uspto-grants-2005_05
特許番号
US06894050B2

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