1,3-Dichloroacetone → 2-Amino-4-[4-(2-azidoethoxy)phenyl]-6-[({2-[(4-fluorophenyl)amino]-1,3-thiazol-4-yl}methyl)thio]pyridine-3,5-dicarbonitrile

HRID 2362820ノート

反応式

HRID 2362820 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH2:11])=[S:10])=[CH:4][CH:3]=1.Cl[CH2:13][C:14]([CH2:16]Cl)=O.[NH2:18][C:19]1[C:24]([C:25]#[N:26])=[C:23]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]=[N+:37]=[N-:38])=[CH:29][CH:28]=2)[C:22]([C:39]#[N:40])=[C:21]([SH:41])[N:20]=1.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:18][C:19]1[C:24]([C:25]#[N:26])=[C:23]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:34][CH2:35][N:36]=[N+:37]=[N-:38])=[CH:31][CH:32]=2)[C:22]([C:39]#[N:40])=[C:21]([S:41][CH2:16][C:14]2[N:11]=[C:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[S:10][CH:13]=2)[N:20]=1

参加物

6

反応物 4

HCID 107931,3-DichloroacetoneHCID 516892Sodium Bicarbonate2 回HCID 6930614-FluorophenylthioureaHCID 178510482HCID 178510482、化合物

生成物 1

HCID 866243362-Amino-4-[4-(2-azidoethoxy)phenyl]-6-[({2-[(4-fluorophenyl)amino]-1,3-thiazol-4-yl}methyl)thio]pyridine-3,5-dicarbonitrile

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 74 mg (0.44 mmol) of 4-fluorophenylthiourea and 55 mg (0.44 mmol) of 1,3-dichloroacetone in 5 ml of ethanol is stirred at +85° C. for 60 min. After removal of the solvent on a rotary evaporator, the residue is taken up in 5 ml of DMF, 105 mg (0.31 mmol) of the compound from Example 38A and 78 mg (0.93 mmol) of sodium bicarbonate are added and the mixture is then stirred at RT for 20 h. The mixture is then added to 15 ml of saturated sodium bicarbonate solution. The mixture is extracted with ethyl acetate (three times, 15 ml each) and the combined organic phases are dried over magnesium sulphate. After removal of the solvent on a rotary evaporator, the crude product is purified chromatographically on silica gel 60 (mobile phase gradient dichloromethane/ethanol 200:1→20:1).

後処理

  1. customAfter removal of the solvent
  2. customon a rotary evaporator
  3. extractionThe mixture is extracted with ethyl acetate (three times, 15 ml each)
  4. dry with materialthe combined organic phases are dried over magnesium sulphate
  5. customAfter removal of the solvent
  6. customon a rotary evaporator
  7. customthe crude product is purified chromatographically on silica gel 60 (mobile phase gradient dichloromethane/ethanol 200:1→20:1)

出典と根拠

ORDレコード
ord-d1b5202be6064da1a2e0e2712e3d42ab
出典データセット
uspto-grants-2014_04
特許番号
US08691850B2

反応ノート

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