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

HRID 884008
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HRID 884008 반응식
[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]
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67040925Methyl 4-(4-(tert-butoxycarbonylamino)phenylthio)-3-(7-isopropylquinazolin-4-ylamino)benzoate

생성물 1

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

시약·촉매·용매 2

HCID 962
Water
용매
2회
HCID 312751,4-Dioxane용매

실험 절차

The product of Example 92D (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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-0152a3e204804ba783a9041919145117
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08236950B2

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