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Hydrochloric Acid → 4-(4-(Tert-butoxycarbonylamino)phenylthio)-3-(7-isopropylquinazolin-4-ylamino)benzoic acid

HRID 605388
ノート
印刷プレビュー

反応式

HRID 605388 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][C:17]=2[NH:26][C:27]2[C:36]3[C:31](=[CH:32][C:33]([CH:37]([CH3:39])[CH3:38])=[CH:34][CH:35]=3)[N:30]=[CH:29][N:28]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>O1CCOCC1.O>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][C:17]=2[NH:26][C:27]2[C:36]3[C:31](=[CH:32][C:33]([CH:37]([CH3:39])[CH3:38])=[CH:34][CH:35]=3)[N:30]=[CH:29][N:28]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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 168937Lithium hydroxide, monohydrateHCID 67040925Methyl 4-(4-(tert-butoxycarbonylamino)phenylthio)-3-(7-isopropylquinazolin-4-ylamino)benzoate

生成物 1

HCID 670411334-(4-(Tert-butoxycarbonylamino)phenylthio)-3-(7-isopropylquinazolin-4-ylamino)benzoic acid収率 88%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
2 回
HCID 312751,4-Dioxane溶媒

実験手順

The product of Example 432D (0.505 g, 0.927 mmol) was suspended in 1,4-dioxane (6 mL), treated with a solution of lithium hydroxide monohydrate (0.078 g, 1.85 mmol) in water (3 mL) at room temperature, then heated at 50° for one hour. The reaction was diluted with water (25 mL), adjusted to pH 1 with 1N aqueous HCl, and extracted with ethyl acetate (50 mL). The organic extract was washed with water (25 mL) and brine (25 mL), dried over magnesium sulfate, filtered, and concentrated by rotary evaporation to afford the title compound as a light yellow solid (0.433 g, 0.816 mmol, 88%). 1H NMR (300 MHz, DMSO-D6) δ ppm 1.31 (d, J=6.99 Hz, 6 H) 1.48 (s, 9 H) 2.98-3.23 (m, 1 H) 6.92 (d, J=8.09 Hz, 1 H) 7.36 (d, J=8.46 Hz, 2 H) 7.54 (d, J=8.82 Hz, 2 H) 7.59 (d, J=11.77 Hz, 1 H) 7.73 (d, J=8.09 Hz, 1 H) 7.89 (s, 1 H) 8.34-8.49 (m, 2 H) 9.61 (s, 1 H) 9.94 (s, 1 H). MS (ESI+) m/z 531 (M+H)+.

後処理

  1. temperatureheated at 50° for one hour
  2. extractionextracted with ethyl acetate (50 mL)
  3. extractionThe organic extract
  4. washwas washed with water (25 mL) and brine (25 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-72d39934fce54413b64231f3a8cfc39a
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07910595B2

反応ノート

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