Dichloromethane → [4-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl)-phenyl]-methanol dihydrochloride

HRID 220562

反応式

HRID 220562 の反応式
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([C:20]3[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][CH:21]=3)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(Cl)[Cl:36]>>[ClH:36].[ClH:36].[N:11]1([C:14]2[C:19]([C:20]3[CH:21]=[CH:22][C:23]([CH2:26][OH:27])=[CH:24][CH:25]=3)=[N:18][CH:17]=[CH:16][N:15]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

参加物

4

反応物 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 685946841,1-Dimethylethyl 4-[3-[4-(hydroxymethyl)phenyl]-2-pyrazinyl]-1-piperazinecarboxylate

生成物 1

HCID 68595263[4-(3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-3'-yl)-phenyl]-methanol dihydrochloride収率 65%

実験手順

Dissolve 3′-(4-hydroxymethyl-phenyl)-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester (2.76 g, 7.45 mmol) in DCM (25 mL) and add trifluoroacetic acid (5 mL) and allow the mixture to stir at room temperature for six hr. Evaporate the solution then dilute with DCM and wash with saturated sodium bicarbonate. Dry the organics over sodium sulfate then filter and evaporate. Chromatograph the residue over silica gel (eluting with 8:92 methanol (with 2 M ammonia):DCM), then dissolve the solid in methanol and add ammonium chloride then sonicate the mixture for 10 min. Evaporate the solution to give [4-(3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-yl)-phenyl]-methanol dihydrochloride as a white solid (1.303 g, 65%). MS (ES): m/z=271 [M+H]+.

後処理

  1. customEvaporate the solution
  2. additionthen dilute with DCM
  3. washwash with saturated sodium bicarbonate
  4. dry with materialDry the organics over sodium sulfate
  5. filtrationthen filter
  6. customevaporate
  7. dissolutionChromatograph the residue over silica gel (eluting with 8:92 methanol (with 2 M ammonia):DCM), then dissolve the solid in methanol
  8. additionadd ammonium chloride
  9. customthen sonicate the mixture for 10 min
  10. customEvaporate the solution

出典と根拠

ORDレコード
ord-4bb3cdcb86504f3cb354cd2f4cd87ebb
出典データセット
uspto-grants-2012_06
特許番号
US08202873B2

関連ノート

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