1,2-Dichloroethane → 2-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]-N-propylacetamide

HRID 1480594ノート

反応式

HRID 1480594 の反応式
[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:7]2[N:8]=[C:9]([S:11][CH2:12][C:13]([OH:15])=O)[S:10][C:6]=2[CH:5]=1)[CH3:2].[CH2:18]([NH2:21])[CH2:19][CH3:20].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)(Cl)Cl.CCOC(C)=O>[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:7]2[N:8]=[C:9]([S:11][CH2:12][C:13]([NH:21][CH2:18][CH2:19][CH3:20])=[O:15])[S:10][C:6]=2[CH:5]=1)[CH3:2]

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 7852PropylamineHCID 757711-HydroxybenzotriazoleHCID 9419442-[(6-Ethoxy-1,3-benzothiazol-2-yl)sulfanyl]acetic acid

生成物 1

HCID 25688572-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]-N-propylacetamide収率 45.5%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 24 (110.3 mg, 0.41 mmol) and n-propylamine (50.5 mg, 0.50 mmol) in CHCl3 (2.0 ml), HOBt (190 mg, 1.41 mmol) and EDC (120 mg, 0.63 mmol) were added at room temperature. After stirring for 20 hours, the reaction mixture was diluted with EtOAc, washed with saturated NaHCO3 solution and brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by HPLC (gradient from 20%, acetonitrile 80% in DDW to 100% acetonitrile, in 15 minutes) to give 33 (57.9 mg, 36% yield) as a brown amorphous solid, range of m.p. temperature was too large for a clear determination. 1H NMR (DMSO-d6): δ 0.97 (t, 3H, J=6.8), δ 1.27 (t, 3H, J=7.1), δ 1.53 (m, 2H, J=6.8, 3.5), δ 3.54 (d, 2H, J=3.7), δ 4.01 (s, 2H), δ 4.19 (q, 2H, J=7.3), δ 6.23 (amide broad peak), δ 6.97 (dd, 1H, J=10.8, J=3.7), 7.33 (d, 2H, J=8.8). 13C NMR (DMSO-d6): δ 12.8, 13.76, 20.6, 39.56, 40.78, 65.1, 101.79, 114.78, 123.6, 135.79, 145.8, 154.67, 168.4, 169.95. MS: MW=310.07 g/mol, MNa+=333.18 g/mol.

後処理

  1. washwashed with saturated NaHCO3 solution and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by HPLC (gradient from 20%, acetonitrile 80% in DDW to 100% acetonitrile, in 15 minutes)

出典と根拠

ORDレコード
ord-6ecbf8013fee476bb7a130287d06b5fc
出典データセット
uspto-grants-2016_08
特許番号
US09409904B2

反応ノート

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