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

HRID 1480594노트

반응식

HRID 1480594 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6ecbf8013fee476bb7a130287d06b5fc
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409904B2

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