Water → 4-[Bis-(3-methyl-pyridin-2-ylmethyl)-amino-]butyl-cyanamide

HRID 1592483ノート

反応式

HRID 1592483 の反応式
[CH3:1][C:2]1[C:3]([CH2:8][N:9]([CH2:15][C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])=[N:4][CH:5]=[CH:6][CH:7]=1.CC([O-])=O.[Na+].[N:28]#[C:29]Br.O>CO>[CH3:1][C:2]1[C:3]([CH2:8][N:9]([CH2:15][C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:29]#[N:28])=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 517045Sodium AcetateHCID 11460737N1,N1-bis-(3-methyl-pyridin-2-ylmethyl)-butane-1,4-diamine

生成物 1

HCID 589970734-[Bis-(3-methyl-pyridin-2-ylmethyl)-amino-]butyl-cyanamide収率 74%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a 0° C. solution of N1,N1-bis-(3-methyl-pyridin-2-ylmethyl)-butane-1,4-diamine (237 mg, 0.80 mmol) in MeOH (10 mL) was added NaOAc (200 mg, 2.39 mmol) and cyanogen bromide (94 mg, 1.03 mmol) and stirred at room temperature for 17 hours. Water (10 mL) was added and the reaction mixture was extracted with CH2Cl2 (4×40 mL). The extracts were washed with brine (20 mL), dried (Na2SO4), filtered and concentrated to provide pure COMPOUND 198 as a beige solid (190 mg, 74%). 1H NMR (CDCl3) δ 1.45-1.51 (m, 2H), 1.65-1.63 (m, 2H), 2.12 (s, 6H), 2.61-2.65 (m, 2H), 2.83-2.89 (m, 2H), 3.68 (s, 4H), 7.08 (dd, 2H, J=4.2, 7.8 Hz), 7.38 (d, 2H, J=7.8 Hz), 7.57 (br s, 1H), 8.37 (d, 2H, J=4.2 Hz). 3C NMR (CDCl3) δ 18.5, 21.1, 28.3, 44.4, 53.6, 58.2, 118.9, 122.9, 133.4, 138.6, 146.6, 156.7. ES-MS m/z 324 (M+H). Anal. Calcd. for C19H25N5.0.4 CH2Cl2O.0.1CH40: C, 64.95; H, 7.32; N, 19.42. Found: C, 64.65; H, 7.22; N, 19.27.

後処理

  1. extractionthe reaction mixture was extracted with CH2Cl2 (4×40 mL)
  2. washThe extracts were washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-708b13498b7c4b778e95f90a9e51164b
出典データセット
uspto-grants-2007_11
特許番号
US07291631B2

反応ノート

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