Dimethylamine → 3-[4-(Cyclopropyl-methyl-amino)-5,6,7,8-tetrahydro-[1]benzothiopheno[2,3-d]pyrimidin-2-yl]-N,N-dimethyl-propionamide

HRID 1056844ノート

反応式

HRID 1056844 の反応式
[CH:1]1([N:4]([CH3:23])[C:5]2[C:6]3[C:18]4[CH2:19][CH2:20][CH2:21][CH2:22][C:17]=4[S:16][C:7]=3[N:8]=[C:9]([CH2:11][CH2:12][C:13](O)=[O:14])[N:10]=2)[CH2:3][CH2:2]1.C[CH2:25][N:26]=[C:27]=NCCCN(C)C.Cl.C(N(CC)CC)C.CNC>C1COCC1>[CH:1]1([N:4]([CH3:23])[C:5]2[C:6]3[C:18]4[CH2:19][CH2:20][CH2:21][CH2:22][C:17]=4[S:16][C:7]=3[N:8]=[C:9]([CH2:11][CH2:12][C:13]([N:26]([CH3:27])[CH3:25])=[O:14])[N:10]=2)[CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 716677593-[4-(Cyclopropyl-methyl-amino)-5,6,7,8-tetrahydro-[1]benzothiopheno[2,3-d]pyrimidin-2-yl]-propionic acid

生成物 1

HCID 716677603-[4-(Cyclopropyl-methyl-amino)-5,6,7,8-tetrahydro-[1]benzothiopheno[2,3-d]pyrimidin-2-yl]-N,N-dimethyl-propionamide収率 51%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of 3-[4-(cyclopropyl-methyl-amino)-5,6,7,8-tetrahydro-[1]benzothiopheno[2,3-d]pyrimidin-2-yl]-propionic acid (0.2 g, 0.0006 mol) and EDC HCl (0.116 g, 0.0006 mol) in THF (10 ml) was added triethyl amine (0.122 g, 0.0012 mol), and the resulting mixture was stirred at R.T for 15 min. The dimethyl amine (0.0027 g, 0.0006 mol) in THF was added dropwise to the reaction mixture and stirring at R.T was continued for another 4 hrs. The solvent was removed; the reaction mixture was diluted with water and extracted with ethyl acetate (3×10 ml). The combined organic layers were dried over Na2SO4, concentrated. The crude material was subjected to column purification on 60-120 silica using ethyl acetate (50%) in hexane to give 0.05 g (51%) of the desired product as off-white solid. 1H NMR (400 MHz, CDCl3) δ ppm=0.43 (m, 2H), 0.69 (m, 2H), 1.75 (m, 2H), 1.89 (m, 2H), 2.85 (m, 7H), 2.94 (s, 3H), 3.0 (s, 3H), 3.05 (s, 3H), 3.20 (t, 2H). LC-MS: [M+H]=359.3.

後処理

  1. stirringstirring at R.T
  2. waitwas continued for another 4 hrs
  3. customThe solvent was removed
  4. additionthe reaction mixture was diluted with water
  5. extractionextracted with ethyl acetate (3×10 ml)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude material was subjected to column purification on 60-120 silica

出典と根拠

ORDレコード
ord-32c0448a5d41441cb2c61363f76acdf3
出典データセット
uspto-grants-2016_07
特許番号
US09399647B2

反応ノート

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