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

反応式

HRID 341499 の反応式
[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]

参加物

6

反応物 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-ol2 回HCID 1296629601,8-Diazabicycloundec-7ene

生成物 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-trichloroethanecarboximidate収率 91%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-d7c52dbed6844ba1b98c1c7681c50f04
出典データセット
uspto-grants-2014_11
特許番号
US08895733B2

関連ノート

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