Cesium carbonate → 2-{[5-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridin-2-yl]oxy}acetonitrile

HRID 341443ノート

反応式

HRID 341443 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[CH:22]=[CH:23][C:24]([OH:27])=[N:25][CH:26]=3)[O:18][N:17]=2)[N:3]=1.I[CH2:29][C:30]#[N:31].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[NH2:1][C:2]1[N:7]=[C:6]([N:8]([CH3:15])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:5]=[C:4]([C:16]2[N:20]=[C:19]([C:21]3[CH:22]=[CH:23][C:24]([O:27][CH2:29][C:30]#[N:31])=[N:25][CH:26]=3)[O:18][N:17]=2)[N:3]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 69356Iodoacetonitrile2 回HCID 178482120HCID 178482120、化合物2 回

生成物 1

HCID 569419822-{[5-(3-{4-Amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridin-2-yl]oxy}acetonitrile収率 2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 5-(3-{4-amino-6-[methyl(phenyl)amino]-1,3,5-triazin-2-yl}-1,2,4-oxadiazol-5-yl)pyridin-2-ol (Intermediate 136, 0.150 g, 0.414 mmol), 2-iodoacetonitrile (0.036 mL, 0.497 mmol), cesium carbonate (0.270 g, 0.827 mmol) in DMF (2 mL) was stirred at 90 C in a pressure tube for 18 h. A further 0.6 equivalent of 2-iodoacetonitrile was added and the mixture was stirred overnight at 90 C. The reaction mixture was cooled to room temperature, diluted with water, the precipitate was collected by filtration, washed with water and dried under vacuum. The resulting solid was purified by preparative HPLC to afford the title compound (3 mg, 2%).

後処理

  1. stirringthe mixture was stirred overnight at 90 C
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with water
  4. customdried under vacuum
  5. customThe resulting solid was purified by preparative HPLC

出典と根拠

ORDレコード
ord-4225f296082d4bbf92a9d5ab08127e04
出典データセット
uspto-grants-2014_11
特許番号
US08895733B2

反応ノート

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