Sodium Bicarbonate → HCID 68458639、化合物

HRID 269776ノート

反応式

HRID 269776 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([N:15]3[CH2:20][CH2:19][CH:18]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[CH2:17][CH2:16]3)=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:26]#[N:27].[Cl:28][C:29]1[CH:30]=[C:31]([CH:33]=[CH:34][C:35]=1[S:36][C:37]1[N:38]([CH3:42])[CH:39]=[CH:40][N:41]=1)[NH2:32].Cl.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(OCCO)C>[Cl:28][C:29]1[CH:30]=[C:31]([NH:32][C:2]2[C:11]3[C:6](=[CH:7][C:8]([N:15]4[CH2:20][CH2:19][CH:18]([N:21]5[CH2:22][CH2:23][CH2:24][CH2:25]5)[CH2:17][CH2:16]4)=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=3)[N:5]=[CH:4][C:3]=2[C:26]#[N:27])[CH:33]=[CH:34][C:35]=1[S:36][C:37]1[N:38]([CH3:42])[CH:39]=[CH:40][N:41]=1

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 10176127Pyridinium chlorideHCID 114590883-chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)phenylamineHCID 68460168HCID 68460168、化合物

生成物 1

HCID 68458639HCID 68458639、化合物収率 60.9%

試薬・触媒・溶媒 1

HCID 8076Glycol monoethyl ether溶媒

反応条件

温度
105 °C

実験手順

A mixture of 0.5 g (1.45 mmol) of 4-chloro-6-nitro-7-(4-pyrrolidin-1-ylpiperidin-1-yl)quinoline-3-carbonitrile, 0.38 g (1.6 mmol) of 3-chloro-4-[(1-methyl-1H-imidazole-2-yl)sulfanyl]aniline and 0.17 g of pyridine hydrochloride in 7.0 mL of 2-ethoxyethanol is heated at 105° C. for 1 hour. After cooling to room temperature, the mixture is stirred with 15 mL of saturated solution of sodium bicarbonate. The resulting solid is collected by filtration and washed with water. Some of the product dissolves in water, which is recovered by extracting the aqueous layer with solution of 95:5 methylene chloride/methanol. The organic layer is evaporated to provide crude product. The combined solids are purified by silica gel chromatography (gradient 95:5methylene chloride/methanol to 4:1 methylene chloride/methanol) gives 0.52 g of 4-({3-chloro-4-[(1-methyl-1H-imidazole-2-yl)thio]phenyl}amino)-6-nitro-7-(4-pyrrolidin-1-ylpiperidin-1-yl)quinoline-3-carbonitrile as an orange solid, mp 220-230° C.

後処理

  1. temperatureAfter cooling to room temperature
  2. filtrationThe resulting solid is collected by filtration
  3. washwashed with water
  4. dissolutionSome of the product dissolves in water
  5. customwhich is recovered
  6. extractionby extracting the aqueous layer with solution of 95:5 methylene chloride/methanol
  7. customThe organic layer is evaporated
  8. customto provide crude product
  9. customThe combined solids are purified by silica gel chromatography (gradient 95:5methylene chloride/methanol to 4:1 methylene chloride/methanol)

出典と根拠

ORDレコード
ord-7f42b46e2a5c405d9a302493f1e13a8d
出典データセット
uspto-grants-2008_11
特許番号
US07449460B2

反応ノート

読み込み中…