7-Amino-4-(2-(dimethylamino)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one → HCID 178483725, 화합물

HRID 1917132노트

반응식

HRID 1917132 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([CH2:11][CH2:12][N:13]([CH3:15])[CH3:14])[C:9](=[O:16])[CH2:8][O:7][C:6]=2[CH:17]=1.I.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](SC)=[NH:25]>C(O)C.C([O-])(O)=O.[Na+]>[CH3:15][N:13]([CH3:14])[CH2:12][CH2:11][N:10]1[C:9](=[O:16])[CH2:8][O:7][C:6]2[CH:17]=[C:2]([NH:1][C:24]([C:20]3[S:19][CH:23]=[CH:22][CH:21]=3)=[NH:25])[CH:3]=[CH:4][C:5]1=2

참가 물질

5

반응물 2

HCID 242533077-Amino-4-(2-(dimethylamino)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-oneHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide2회

생성물 1

HCID 178483725HCID 178483725, 화합물수율 88%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 516892Sodium Bicarbonate용매

실험 절차

A solution of 7-amino-4-(2-(dimethylamino)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (0.125 g, 0.531 mmol) in dry ethanol (10 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (0.3 g, 1.062 mmol) at room temperature and stirred overnight (18 hours). At this time, additional methyl thiophene-2-carbimidothioate hydroiodide (0.3 g, 1.062 mmol) was added, and stirring was continued for another 24 hours. The reaction was diluted with saturated NaHCO3 solution (20 mL), and the product was extracted into CH2Cl2 (2×20 mL). The combined CH2Cl2 layers were washed with brine (15 mL) and dried (Na2SO4). The solvent was evaporated, and the crude material was purified by column chromatography (5:95 (2M NH3 in MeOH):CH2Cl2) to obtain the title compound 5 (0.16 g, 88%) as a solid. 1H NMR (DMSO-d6) δ 2.19 (s, 6H), 2.43 (t, 2H, J=6.9 Hz), 3.97 (t, 2H, J=6.9 Hz), 4.58 (s, 2H), 6.48-6.58 (m, 4H), 7.06-7.14 (m, 2H), 7.60 (d, 1H, J=5.1 Hz), 7.74 (d, 1H, J=3.3 Hz); ESI-MS (m/z, %): 345 (MH+, 100), 128 (85); ESI-HRMS calculated for C17H21N4O2S (MH+), calculated: 345.1379; observed: 345.1384; HPLC-purity: 93.15% by area.

후처리

  1. stirringstirring
  2. waitwas continued for another 24 hours
  3. extractionthe product was extracted into CH2Cl2 (2×20 mL)
  4. washThe combined CH2Cl2 layers were washed with brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated
  7. customthe crude material was purified by column chromatography (5:95 (2M NH3 in MeOH):CH2Cl2)

출처 및 근거

ORD 기록
ord-40834211b92745a5b1d93cfd7f6fcf8e
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618286B2

반응 노트

불러오는 중…