Hydrochloric Acid → 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(2-(N-(t-butoxycarbonyl)-N-ethylamino)ethyloxyimino)quinazoline

HRID 220113ノート

反応式

HRID 220113 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25](C=O)[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.C(OC([CH2:37][CH2:38][NH:39][CH2:40][CH2:41][O:42][NH2:43])=O)(C)(C)C.Cl.[C:45](=[O:48])(O)[O-:46].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:27]3[CH2:26][C:25](=[N:43][O:42][CH2:41][CH2:40][N:39]([C:45]([O:46][C:10]([CH3:15])([CH3:11])[CH3:9])=[O:48])[CH2:38][CH3:37])[CH:24]=[CH:23][C:22]=3[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 577336564-(3-Chloro-4-(3-fluorobenzyloxy)phenylamino) 6-formylquinazolineHCID 86630917N-(t-butoxycarbonyl)ethylaminoethoxyamine

生成物 1

HCID 866309164-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(2-(N-(t-butoxycarbonyl)-N-ethylamino)ethyloxyimino)quinazoline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In tetrahydrofuran (1.5 ml) were dissolved 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-formylquinazoline (IV-1, 120 mg) and N-(t-butoxycarbonyl)ethylaminoethoxyamine (110 mg), and 134 μl of 2 mol/L hydrochloric acid was added, then the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was poured into aqueous ice-cooled saturated sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was washed with water and aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated. The resulting residue was purified by amino column chromatography (eluting with hexane:ethyl acetate=1:1), and further re-purified by silica gel chromatography (eluting with hexane:ethyl acetate=1:1) to obtain 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-(2-(N-(t-butoxycarbonyl)-N-ethylamino)ethyloxyimino)quinazoline (V-16, 96 mg) as a yellow viscous oil.

後処理

  1. additionwas added
  2. customAfter completion of the reaction
  3. additionthe reaction mixture was poured into aqueous ice-
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe resulting residue was purified by amino column chromatography (eluting with hexane:ethyl acetate=1:1)
  9. customfurther re-purified by silica gel chromatography (eluting with hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-1149d957ec364d2f8f23cff88134330a
出典データセット
uspto-grants-2012_06
特許番号
US08202879B2

反応ノート

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