Water → 1-[6-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl]-1,2,4-oxadiazol-5-yl)pyridin-3-yl}ethyl 2,2,2-trichloroethanecarboximidate

HRID 341499

반응식

HRID 341499 반응식
[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[C:4]([C:16]2[N:20]=[C:19]([C:21]3[N:26]=[CH:25][C:24]([CH:27]([OH:29])[CH3:28])=[CH:23][CH:22]=3)[O:18][N:17]=2)[N:3]=1.[Cl:30][C:31]([Cl:35])([Cl:34])[C:32]#N.[N:36]1(C2CCCCCCCCCC2)CCCN=CCCCC[CH2:37]1.O>C(Cl)Cl>[Cl:30][C:31]([Cl:35])([Cl:34])[CH2:32][C:37](=[NH:36])[O:29][CH:27]([C:24]1[CH:25]=[N:26][C:21]([C:19]2[O:18][N:17]=[C:16]([C:4]3[N:3]=[C:2]([NH2:1])[N:7]=[C:6]([N:8]([CH3:15])[C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[N:5]=3)[N:20]=2)=[CH:22][CH:23]=1)[CH3:28]

참가 물질

6

반응물 4

HCID 962WaterHCID 11011TrichloroacetonitrileHCID 668031951-[6-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl]-1,2,4-oxadiazol-5-yl)pyridin-3-yl}ethan-1-ol2회HCID 1296629601,8-Diazabicycloundec-7ene

생성물 1

HCID 668027621-[6-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl]-1,2,4-oxadiazol-5-yl)pyridin-3-yl}ethyl 2,2,2-trichloroethanecarboximidate수율 91%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

1-[6-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridin-3-yl]ethan-1-ol (Intermediate 140, 0.400 g, 1.02 mmol) was suspended in DCM. Trichloroacetonitrile (0.123 mL, 1.22 mmol) and 1,8-diazabicycloundec-7-ene (few drops) were added and the mixture was stirred at room temperature for 19 h. DCM (30 mL) and water (30 mL) were added, the organic layer was separated and washed with brine (30 mL), before being dried over sodium sulfate and concentrated under vacuum to afford the title compound as a golden-brown solid (0.497 g, 91%), which was used in the next step without further purification. Method C HPLC-MS: MH+ requires m/z=534 Found: m/z=534, Rt=1.55 min (57%).

후처리

  1. customthe organic layer was separated
  2. washwashed with brine (30 mL)
  3. dry with materialbefore being dried over sodium sulfate
  4. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-d7c52dbed6844ba1b98c1c7681c50f04
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895733B2

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