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Formaldehyde → 4-({3-Chloro-4-[(1-methyl-1H-imidazole-2-yl)thio]phenyl}amino)-6-(methylamino)-7-(4-pyrrolidin-1-ylpiperidin-1-yl)quinoline-3-carbonitrile

HRID 499127
ノート
印刷プレビュー

反応式

HRID 499127 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][CH:15]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:14][CH2:13]1)[N:8]=[CH:7][C:6]([C:23]#[N:24])=[C:5]2[NH:25][C:26]1[CH:31]=[CH:30][C:29]([S:32][C:33]2[N:34]([CH3:38])[CH:35]=[CH:36][N:37]=2)=[C:28]([Cl:39])[CH:27]=1.C=O.[C:42]([BH3-])#N.[Na+]>C(O)(=O)C.C(O)C>[Cl:39][C:28]1[CH:27]=[C:26]([NH:25][C:5]2[C:4]3[C:9](=[CH:10][C:11]([N:12]4[CH2:13][CH2:14][CH:15]([N:18]5[CH2:19][CH2:20][CH2:21][CH2:22]5)[CH2:16][CH2:17]4)=[C:2]([NH:1][CH3:42])[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:23]#[N:24])[CH:31]=[CH:30][C:29]=1[S:32][C:33]1[N:34]([CH3:38])[CH:35]=[CH:36][N:37]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68460429HCID 68460429、化合物

生成物 1

HCID 684588494-({3-Chloro-4-[(1-methyl-1H-imidazole-2-yl)thio]phenyl}amino)-6-(methylamino)-7-(4-pyrrolidin-1-ylpiperidin-1-yl)quinoline-3-carbonitrile収率 50.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒
HCID 702
Ethanol
溶媒

実験手順

A mixture of 130 mg (0.23 mmol) of 6-amino-4-[3-chloro-4-(1-methyl-1H-imidazole-2-ylsulfanyl)phenylamino]-7-(4-pyrrolidin-1-yl-piperidin-1-yl)quinoline-3-carbonitrile, 12.0 mg (0.4 mmol) of paraformaldehyde, 25.0 mg (0.39 mmol) of sodium cyanoborohydride and 2 drops of acetic acid in 15 mL of ethanol is heated under reflux for 8 hours. The mixture is cooled to room temperature and solvent removed in vacuo. A 12 mL solution of 1N sodium hydroxide is added to the residue, and the mixture is stirred. A crude solid is collected by filtration, washed with water and dried. Purification by silica gel chromatography (gradient 95:5 methylene chloride/methanol to 4:1 methylene chloride/methanol) gives 66.0 mg of the 4-({3-Chloro-4-[(1-methyl-1H-imidazole-2-yl)thio]phenyl}amino)-6-(methylamino)-7-(4-pyrrolidin-1-ylpiperidin-1-yl)quinoline-3-carbonitrile as an yellow solid, mp 242-250° C.

後処理

  1. temperatureis heated
  2. temperatureunder reflux for 8 hours
  3. customsolvent removed in vacuo
  4. additionA 12 mL solution of 1N sodium hydroxide is added to the residue
  5. filtrationA crude solid is collected by filtration
  6. washwashed with water
  7. customdried
  8. customPurification by silica gel chromatography (gradient 95:5 methylene chloride/methanol to 4:1 methylene chloride/methanol)

出典と根拠

ORDレコード
ord-ab15b89f808b41869118dfa6d6e7f959
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07767671B2

反応ノート

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