Triethylamine → (3-(4-((Dimethylamino)methyl)phenylthio)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

HRID 1035230노트

반응식

HRID 1035230 반응식
Cl.[CH3:2][NH:3][CH3:4].Cl[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH:14]2[CH2:17][N:16]([C:18]([C:20]3[O:21][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:23][N:24]=3)=[O:19])[CH2:15]2)=[CH:9][CH:8]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:2][N:3]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([S:13][CH:14]2[CH2:17][N:16]([C:18]([C:20]3[O:21][C:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:23][N:24]=3)=[O:19])[CH2:15]2)=[CH:11][CH:12]=1)[CH3:4]

참가 물질

5

반응물 3

HCID 8471Triethylamine2회HCID 10473Dimethylamine, hydrochloride2회HCID 58043149(3-(4-(Chloromethyl)phenylthio)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

생성물 1

HCID 56598532(3-(4-((Dimethylamino)methyl)phenylthio)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone수율 86.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Dimethylamine hydrochloride (0.10 g, 1.24 mmol) and 60B (0.16 g, 0.41 mmol) were mixed in DCM (5 ml). Triethylamine (0.290 ml, 2.07 mmol) was added and the mixture was stirred at RT for 2.5 h. More of triethylamine (0.290 ml, 2.07 mmol) and dimethylamine hydrochloride (0.10 g, 1.24 mmol) were added. The mixture was stirred overnight at RT and then diluted with DCM (10 ml). The mixture was washed with water, filtered through a phase separator and then evaporated. The residue was purified by column chromatography eluting with NH3 in MeOH (2M)/DCM (1:99, 2:98). There was obtained 0.14 g (84%) of 60 as a solid. 1H NMR (500 MHz, CDCl3): δ 2.20 (s, 6H), 3.38 (s, 2H), 4.16 (m, 2H), 4.61 (m, 2H), 5.07 (m, 1H), 7.50 (t, 2H), 7.56 (t, 1H), 8.12 (d, 2H), MS (APCI+) m/z 395 [M+H]+, LC purity: 97%.

후처리

  1. stirringThe mixture was stirred overnight at RT
  2. washThe mixture was washed with water
  3. filtrationfiltered through a phase separator
  4. customevaporated
  5. customThe residue was purified by column chromatography
  6. washeluting with NH3 in MeOH (2M)/DCM (1:99, 2:98)

출처 및 근거

ORD 기록
ord-b6d4978c5a0f4dd384bca65d937eba88
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546375B2

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