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1,1'-Carbonyldiimidazole → (R)-(3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidin-1-yl)(4,4-difluoropiperidin-1-yl)methanone

HRID 1969741
ノート
印刷プレビュー

反応式

HRID 1969741 の反応式
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][NH:17][C:14]=4[N:15]=[CH:16][C:11]3=[CH:10][N:9]=2)[CH2:3]1.C1N=CN([C:25]([N:27]2[CH:31]=N[CH:29]=[CH:28]2)=[O:26])C=1.Cl.[F:33][C:34]1([F:40])CCNC[CH2:35]1>N1C=CC=CC=1>[C:8]1([C@@H:4]2[CH2:5][CH2:6][CH2:7][N:2]([C:25]([N:27]3[CH2:28][CH2:29][C:34]([F:40])([F:33])[CH2:35][CH2:31]3)=[O:26])[CH2:3]2)[N:12]2[C:13]3[CH:19]=[CH:18][NH:17][C:14]=3[N:15]=[CH:16][C:11]2=[CH:10][N:9]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 682631,1'-Carbonyldiimidazole2 回HCID 27583514,4-Difluoropiperidine hydrochlorideHCID 67216656(R)-1-(piperidin-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine hydrochloride

生成物 1

HCID 58557191(R)-(3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidin-1-yl)(4,4-difluoropiperidin-1-yl)methanone収率 49.5%

試薬・触媒・溶媒 1

HCID 1049
Pyridine
溶媒

反応条件

温度
50 °C

実験手順

To a solution of (R)-1-(piperidin-3-yl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazine hydrochloride (0.24 g, 0.76 mmol) in pyridine (7.2 mL) was added CDI (0.14 g, 0.87 mmol) and the reaction mixture was stirred at about 50° C. for about 2 h. Additional CDI (0.02 g, 0.14 mmol) was added and the reaction mixture was stirred for about 1 h. To the reaction mixture was added 4,4-difluoropiperidine hydrochloride (0.12 g, 0.76 mmol). The reaction mixture was heated to about 55° C. for about 1 h, cooled to ambient temperature, and stirred for about 2 d. The solvent was removed under reduced pressure and the crude residue dissolved with DCM (5 mL) and washed with water (2 mL). The aqueous layer was back extracted with DCM (2 mL). The combined organic extracts were washed with brine (3 mL), dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 0-5% MeOH in DCM to afford (R)-(3-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)piperidin-1-yl)(4,4-difluoropiperidin-1-yl)methanone (0.146 g, 49%) as an off white solid: LC/MS (Table 1, Method b) Rt=1.70 min; MS m/z: 389 (M+H)+.

後処理

  1. stirringthe reaction mixture was stirred for about 1 h
  2. temperatureThe reaction mixture was heated to about 55° C. for about 1 h
  3. temperaturecooled to ambient temperature
  4. stirringstirred for about 2 d
  5. customThe solvent was removed under reduced pressure
  6. dissolutionthe crude residue dissolved with DCM (5 mL)
  7. washwashed with water (2 mL)
  8. extractionThe aqueous layer was back extracted with DCM (2 mL)
  9. washThe combined organic extracts were washed with brine (3 mL)
  10. dry with materialdried over anhydrous MgSO4
  11. filtrationfiltered
  12. customThe crude material was purified by silica gel chromatography
  13. washeluting with a gradient of 0-5% MeOH in DCM

出典と根拠

ORDレコード
ord-a5a5e04237d642bc8256814e749c3ea5
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08426411B2

反応ノート

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