Cesium carbonate → HCID 131723668、化合物

HRID 1823430ノート

反応式

HRID 1823430 の反応式
CN(C)/[CH:3]=[C:4](\[C:15]1[NH:16][CH:17]=[CH:18][N:19]=1)/[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)=O.Cl.[C:22]([NH:25][CH2:26][CH2:27][NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])(=[NH:24])[NH2:23].C([O-])([O-])=O.[Cs+].[Cs+]>CN1C(=O)CCC1>[C:32]([O:31][C:29]([NH:28][CH2:27][CH2:26][NH:25][C:22]1[N:23]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[CH:11][CH:12]=2)[C:4]([C:15]2[NH:19][CH:18]=[CH:17][N:16]=2)=[CH:3][N:24]=1)=[O:30])([CH3:35])([CH3:34])[CH3:33]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 693105754-[(2E)-3-(dimethylamino)-2-imidazolylprop-2-enoyl]benzenecarbonitrileHCID 178453692HCID 178453692、化合物

生成物 1

HCID 131723668HCID 131723668、化合物収率 83%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒2 回

反応条件

温度
100 °C

実験手順

4-[(2E)-3-(dimethylamino)-2-imidazolylprop-2-enoyl]benzenecarbonitrile (8.0 g, 30.0 mmol) in NMP (5 ml) was added to a stirred mixture of N-[2-(amidinoamino)ethyl](tert-butoxy)carboxamide, hydrochloride (13.8 g, 45 mmol)) and Cs2CO3 (11.72, 36.0 mmol) in NMP (15 ml). The reaction was heated to 100° C. for 48 hours. The reaction was followed by HPLC. Upon completion, the reaction was partitioned with water (50 ml) and dichloromethane (250 ml). The organic layer was separated and washed with water (2×50 ml), brine (50 ml), dried Na2SO4, filtered, and concentrated under reduced pressure. The product was purified by flash chromatography eluting with 10% methanol in dichloromethane. After stripping off the solvents and drying in vacuo, 10.08 g of (tert-butoxy)-N-(2-{[4-(4-cyanophenyl)-5-imidazolylpyrimidin-2-yl]amino}ethyl)carboxamide was obtained as a dark red glass in 83% yield.

後処理

  1. customUpon completion, the reaction was partitioned with water (50 ml) and dichloromethane (250 ml)
  2. customThe organic layer was separated
  3. washwashed with water (2×50 ml), brine (50 ml), dried Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified by flash chromatography
  7. washeluting with 10% methanol in dichloromethane
  8. customdrying in vacuo

出典と根拠

ORDレコード
ord-94c0c5cebfd249218d9bc165ac10a1b0
出典データセット
uspto-grants-2006_05
特許番号
US07037918B2

反応ノート

読み込み中…