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Diisopropylethylamine → 4-(6-methyl-2-pyridinyl)-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2(1H)-pyrimidinone dihydrochloride

HRID 1514446
ノート
印刷プレビュー

反応式

HRID 1514446 の反応式
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=2)=[N:8][C:7]1=[O:19].[F:20][C:21]([F:35])([F:34])[C:22]1[CH:27]=[CH:26][C:25]([C@:28]23[CH2:33][C@H:32]2[CH2:31][NH:30][CH2:29]3)=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>CCO>[ClH:1].[ClH:1].[CH3:18][C:14]1[N:13]=[C:12]([C:9]2[CH:10]=[CH:11][N:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:30]3[CH2:31][C@H:32]4[C@:28]([C:25]5[CH:24]=[CH:23][C:22]([C:21]([F:20])([F:35])[F:34])=[CH:27][CH:26]=5)([CH2:33]4)[CH2:29]3)[C:7](=[O:19])[N:8]=2)[CH:17]=[CH:16][CH:15]=1
参加物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 81531DiisopropylethylamineHCID 592428011-(4-Chloro-butyl)-4-(6-methyl-pyridin-2-yl)-1H-pyrimidin-2-oneHCID 59337591(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

生成物 1

HCID 686973904-(6-methyl-2-pyridinyl)-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2(1H)-pyrimidinone dihydrochloride収率 36.9%

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

実験手順

A solution of 1-(4-chloro-butyl)-4-(6-methyl-pyridin-2-yl)-1H-pyrimidin-2-one (Prep17, 48 mg, 0.17 mmol), (1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hexane (Prep4, 38 mg, 0.17 mmol), KI (2 mg) and DIPEA (66 mg, 0.51 mmol) in absolute EtOH (2 ml) was placed in a microwave oven and irradiated at 125° C. for 13 hours. The solvent was removed under vacuum and the residue was redissolved in DCM and filtered. The filtrate was stirred in the presence of PS-isocyanate (350 mg) for 3 hours. The mixture was filtered and the solvent removed under vacuum. The crude was purified by flash chromatography with DCM-MeOH—NH4OH (99-1-0.1) to give the title compound (17 mg, 4% yield) as a free base.

後処理

  1. customirradiated at 125° C. for 13 hours
  2. customThe solvent was removed under vacuum
  3. dissolutionthe residue was redissolved in DCM
  4. filtrationfiltered
  5. filtrationThe mixture was filtered
  6. customthe solvent removed under vacuum
  7. customThe crude was purified by flash chromatography with DCM-MeOH—NH4OH (99-1-0.1)

出典と根拠

ORDレコード
ord-011686e4a1294291b5ab0e9ead0cc314
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08222266B2

反応ノート

読み込み中…

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