1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 6-((5-(4-chlorophenylamino)-1,3,4-oxadiazol-2-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one

HRID 1023162노트

반응식

HRID 1023162 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][NH:12][C:13](=[O:27])[CH2:14][O:15][C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[NH:22][C:21](=[O:26])[CH2:20][CH2:19]3)=S)=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[O:27][C:13]([CH2:14][O:15][C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[NH:22][C:21](=[O:26])[CH2:20][CH2:19]4)=[N:12][N:11]=2)=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86680403N-(4-chlorophenyl)-2-(2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)acetyl)hydrazinecarbothioamide

생성물 1

HCID 715418456-((5-(4-chlorophenylamino)-1,3,4-oxadiazol-2-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one수율 38.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of N-(4-chlorophenyl)-2-(2-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)acetyl)hydrazinecarbothioamide (0.2 g, 0.49 mmol) in dry DMF (10 mL) at room temperature, EDC HCl (0.189 g, 0.98 mmol) and TEA (0.148 g 1.4 6 mmol) were added. The reaction was stirred at room temperature overnight and monitored by LCMS. The solvent was removed under vacuum and then water (20 mL) was added to the residue. The solid which formed was filtered, dried, and the crude product (0.15 g) was recrystallized in a mixture of ethanol/ACN to afford 6-((5-(4-chlorophenylamino)-1,3,4-oxadiazol-2-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one (70 mg, 38%) as an off white solid. 1H NMR: 400 MHZ, DMSO-d6: δ 2.41 (t, J=7.20 Hz, 2H), 2.85 (t, J=8.00 Hz, 2H), 5.23 (s, 2H), 6.80 (d, J=8.40 Hz, 1H), 6.87 (dd, J=2.80, 8.40 Hz, 1H), 6.94 (d, J=2.40 Hz, 1H), 7.42 (dd, J=2.00, 6.80 Hz, 2H), 7.58 (dd, J=2.40, 6.80 Hz, 2H), 9.96 (s, 1H), 10.77 (s, 1H). LCMS: RT 1.50 min, LCMS (ES-API), m/z 371.0 (M+H).

후처리

  1. customThe solvent was removed under vacuum
  2. additionwater (20 mL) was added to the residue
  3. customThe solid which formed
  4. filtrationwas filtered
  5. customdried
  6. customthe crude product (0.15 g) was recrystallized in a mixture of ethanol/ACN

출처 및 근거

ORD 기록
ord-1b192fb4119147ae8d1e696810e918ca
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722670B2

반응 노트

불러오는 중…