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

HRID 2362827
ノート
印刷プレビュー

反応式

HRID 2362827 の反応式
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]=[N+]=[N-])=[CH:12][CH:11]=2)[C:5]([C:22]#[N:23])=[C:4]([S:24][CH2:25][C:26]2[N:27]=[C:28]([NH:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)[S:29][CH:30]=2)[N:3]=1.[H][H].[ClH:41]>O1CCOCC1.[Pd]>[ClH:41].[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][NH2:19])=[CH:14][CH:15]=2)[C:5]([C:22]#[N:23])=[C:4]([S:24][CH2:25][C:26]2[N:27]=[C:28]([NH:31][C:32]3[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=3)[S:29][CH:30]=2)[N:3]=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 313Hydrochloric AcidHCID 866243362-Amino-4-[4-(2-azidoethoxy)phenyl]-6-[({2-[(4-fluorophenyl)amino]-1,3-thiazol-4-yl}methyl)thio]pyridine-3,5-dicarbonitrileHCID 178418361HCID 178418361、化合物2 回

生成物 1

HCID 866243382-Amino-4-[4-(2-aminoethoxy)phenyl]-6-[({2-[(4-fluorophenyl)amino]-1,3-thiazol-4-yl}methyl)-thio]pyridine-3,5-dicarbonitrile hydrochloride

試薬・触媒・溶媒 2

HCID 23938
Palladium
触媒
HCID 312751,4-Dioxane溶媒

実験手順

1000 mg (1.84 mmol) of the compound from Example 39A are dissolved in 100 ml of dioxane, 150 mg (1.41 mmol) of palladium-on-activated carbon are added and the mixture is hydrogenated with hydrogen at 3 bar. After 3 h, 4 ml of 2M hydrochloric acid are added and the mixture is hydrogenated with hydrogen at 3 bar for a further 20 h. The mixture is then filtered off with suction through a Seitz clarifying sheet filter, the product is then washed with 50 ml of dioxane, and 50 ml of toluene are added to the filtrate. After removal of the solvent on a rotary evaporator, the residue is taken up in a mixture of 50 ml of water and 50 ml of ethyl acetate. By cautious addition of aqueous dilute sodium bicarbonate solution, the pH is adjusted to about pH 9. The phases formed are separated. The organic phase is dried over magnesium sulphate, the solvent is then removed using a rotary evaporator and the residue is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5, with addition of 0.5% concentrated hydrochloric acid). The product-containing fractions are combined and concentrated using a rotary evaporator.

後処理

  1. filtrationThe mixture is then filtered off with suction through a Seitz clarifying sheet
  2. filtrationfilter
  3. washthe product is then washed with 50 ml of dioxane, and 50 ml of toluene
  4. additionare added to the filtrate
  5. customAfter removal of the solvent
  6. customon a rotary evaporator
  7. additionthe residue is taken up in a mixture of 50 ml of water and 50 ml of ethyl acetate
  8. additionBy cautious addition of aqueous dilute sodium bicarbonate solution
  9. customThe phases formed
  10. customare separated
  11. dry with materialThe organic phase is dried over magnesium sulphate
  12. customthe solvent is then removed
  13. customa rotary evaporator
  14. customthe residue is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5, with addition of 0.5% concentrated hydrochloric acid)
  15. concentrationconcentrated
  16. customa rotary evaporator

出典と根拠

ORDレコード
ord-3df2db9cf64a46788aca2eede6cc03ff
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08691850B2

反応ノート

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