Dimethylamine → (5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(3-dimethylaminomethyl-4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester

HRID 1925002ノート

反応式

HRID 1925002 の反応式
[Br:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([N:11]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:12]2[CH:13]=[CH:14][C:15]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[C:16]([CH:23]=2)[CH2:17]OS(C)(=O)=O)=[N:4][CH:3]=1.[CH3:37][NH:38][CH3:39].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[NH3:4].[C:33]([O:32][C:30](=[O:31])[N:11]([C:5]1[C:6]2[N:7]([CH:8]=[CH:9][N:10]=2)[C:2]([Br:1])=[CH:3][N:4]=1)[C:12]1[CH:13]=[CH:14][C:15]([N:24]2[CH2:25][CH2:26][O:27][CH2:28][CH2:29]2)=[C:16]([CH2:17][N:38]([CH3:39])[CH3:37])[CH:23]=1)([CH3:35])([CH3:34])[CH3:36]

参加物

6

反応物 3

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 86652630Methanesulfonic acid 5-[(5-bromo-imidazo[1,2-a]pyrazin-8-yl)-tert-butoxycarbonyl-amino]-2-morpholin-4-yl-benzyl ester

生成物 2

HCID 222AmmoniaHCID 86652631(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(3-dimethylaminomethyl-4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester収率 61%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
75 °C

実験手順

To a solution of methanesulfonic acid 5-[(5-bromo-imidazo[1,2-a]pyrazin-8-yl)-tert-butoxycarbonyl-amino]-2-morpholin-4-yl-benzyl ester (0.098 g, 0.169 mmol) in THF (0.5 mL) is added 2M N,N-dimethylamine solution in THF (0.50 mL, 1.1 mmol) followed by K2CO3 (0.028 g, 0.202 mmol). The reaction mixture is stirred at room temperature for 1.5 hours and at 75° C. for an additional 3 hours. The solvent is removed under vacuum and the residue is partitioned between ethyl acetate and water. The organic layer is dried over MgSO4, filtered and concentrated in vacuo to give the crude compound which is purified by silica gel column chromatography. Elution using 97:3 DCM:NH3 (7M in MeOH) affords the title compound (0.0543 g, 61%). LCMS: Rt 2.37 min (95%), m/z (ES+) 531/533 (M+H)+.

後処理

  1. customThe solvent is removed under vacuum
  2. customthe residue is partitioned between ethyl acetate and water
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give the crude compound which
  7. customis purified by silica gel column chromatography
  8. washElution

出典と根拠

ORDレコード
ord-c725af116c1c4a06b43680fa4cb3b4fb
出典データセット
uspto-grants-2012_05
特許番号
US08178530B2

反応ノート

読み込み中…