Cyclopropylamine → 8-(2-(Cyclopropylamino)-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

HRID 1501849ノート

反応式

HRID 1501849 の反応式
[CH3:1][C:2]1[C:10]([C:11](=O)[CH2:12][N:13]2[CH2:30][CH2:29][C:16]3([C:20](=[O:21])[N:19]([C:22]4[CH2:23][O:24][C:25](=[O:28])[C:26]=4[CH3:27])[CH2:18][CH2:17]3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:32].[CH:33]1([NH2:36])[CH2:35][CH2:34]1.[BH3-]C#N.[Na+]>CC(O)=O.C1COCC1>[CH:33]1([NH:36][CH:11]([C:10]2[C:2]([CH3:1])=[C:3]3[C:7](=[CH:8][CH:9]=2)[C:6](=[O:32])[O:5][CH2:4]3)[CH2:12][N:13]2[CH2:30][CH2:29][C:16]3([C:20](=[O:21])[N:19]([C:22]4[CH2:23][O:24][C:25](=[O:28])[C:26]=4[CH3:27])[CH2:18][CH2:17]3)[CH2:15][CH2:14]2)[CH2:35][CH2:34]1

参加物

5

反応物 3

HCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 867095278-(2-(4-Methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)-2-oxoethyl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

生成物 1

HCID 729484658-(2-(Cyclopropylamino)-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one

試薬・触媒・溶媒 1

HCID 23444217Acetic acid tetrahydrofuran溶媒

実験手順

To a mixture of 8-(2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)-2-oxoethyl)-2-(4-methyl-5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decan-1-one (25 mg, 0.057 mmol) and cyclopropanamine (6.5 mg, 0.114 mmol) in anhydrous 5% HOAc/THF (1 mL) was added NaCNBH3 (18 mg, 0.28 mmol). The reaction was sealed and shaken at ambient temperature for 16 h. LCMS showed that the product was formed. The reaction was quenched with water (0.5 mL) and the solvent was evaporated under reduced pressure. The residue was dissolved in DMSO (1.5 mL) and filtered. The crude product was purified by using reversed-phase HPLC (Acetonitrile with 0.1% TFA: water with 0.1% TFA from 10% to 60%) to give the title compound. LC-MS (IE, m/z): 480 [M+1]+.

後処理

  1. customThe reaction was sealed
  2. customwas formed
  3. customThe reaction was quenched with water (0.5 mL)
  4. customthe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in DMSO (1.5 mL)
  6. filtrationfiltered
  7. customThe crude product was purified

出典と根拠

ORDレコード
ord-223b75c47dbb4447a539ae8c7fcc6eb3
出典データセット
uspto-grants-2015_12
特許番号
US09206198B2

反応ノート

読み込み中…