Dichloromethane → HCID 69192623, 화합물

HRID 1020273노트

반응식

HRID 1020273 반응식
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][OH:7].[F:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=1)[CH2:12][NH:13][C:14]([NH:16][C:17]1[S:21][N:20]=[C:19]([CH2:22]Cl)[N:18]=1)=[O:15].ClCCl>C1COCC1>[F:8][C:9]1[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=1)[CH2:12][NH:13][C:14]([NH:16][C:17]1[S:21][N:20]=[C:19]([CH2:22][O:7][CH2:6][CH2:5][O:4][CH3:3])[N:18]=1)=[O:15]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 58055089HCID 58055089, 화합물2회

생성물 1

HCID 69192623HCID 69192623, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Sodium hydride (4 eq, 2.66 mmol, 0.13 g of a 50 wt-% suspension in oil) was suspended in THF (2 mL) and cooled to 0° C. 2-methoxy ethanol (3 eq, 1.99 mmol, 0.15 g) and 15-crown-5-ether (1 drop) were added. 1-(3-Fluorobenzyl)-3-(3-(chloromethyl)-1,2,4-thiadiazol-5-yl)urea (Intermediate XXV) was added and the mixture was stirred over night with temperature allowed to rise to room temperature. Dichloromethane (50 mL) was added. The mixture was washed with water (2×10 mL), dried (Na2SO4), filtered and concentrated in vacuo. The crude material (0.2 g of an oil) was further purified by preparative HPLC to give 0.101 g. 1H-NMR (300 MHz, CD3OD): δ 7.34 (m, 1H), 7.14 (d, 1H), 7.07 (d, 1H), 6.99 (m, 1H), 4.58 (s, 2H), 4.45 (s, 2H), 3.70 (t, 2H), 3.56 (t, 2H), 3.30 (s, 3H).

후처리

  1. customto rise to room temperature
  2. washThe mixture was washed with water (2×10 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material (0.2 g of an oil) was further purified by preparative HPLC
  7. customto give 0.101 g

출처 및 근거

ORD 기록
ord-f5f8a67c92dd4b9f9370aa846e916fce
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716320B2

반응 노트

불러오는 중…