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Hydrochloric Acid → HCID 71667659, 화합물

HRID 928954
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HRID 928954 반응식
[F:1][C:2]1[C:7]2[N:8]=[CH:9][O:10][C:6]=2[CH:5]=[C:4]([C:11]([NH:13][O:14][CH2:15][CH2:16][O:17]C=C)=[O:12])[C:3]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=1[F:28].Cl>C(Cl)Cl>[F:1][C:2]1[C:7]2[N:8]=[CH:9][O:10][C:6]=2[CH:5]=[C:4]([C:11]([NH:13][O:14][CH2:15][CH2:16][OH:17])=[O:12])[C:3]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=1[F:28]
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참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 89704805HCID 89704805, 화합물

생성물 1

HCID 71667659HCID 71667659, 화합물수율 88.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of compound 4-fluoro-5-((2-fluoro-4-iodophenyl)amino)-N-(2-(vinyloxy)ethoxy)benzo[d]oxazole-6-carboxamide (450 mg, 0.9 mmol) in CH2Cl2 (10 mL) was added 1.0 N HCl (aq., 6.7 mL, 6.72 mmol). After stirring for 1 h, the reaction mixture was washed with saturated NaHCO3 (aq.). The aqueous layer was washed with CH2Cl2 (10 mL×2). The combined organic layer was washed with water (10 mL) and brine (10 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel (CH2Cl2/MeOH, 50:1, v/v) and gave the desired product (white solid, 380 mg, 88.9% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.75 (s, 1H), 8.96 (s, 1H), 8.01 (s, 1H), 7.88 (s, 1H), 7.53 (d, J=9.4 Hz, 1H), 7.28 (d, J=8.7 Hz, 1H), 6.39 (m, 1H), 4.70 (s, 1H), 3.83 (s, 2H), 3.56 (s, 2H). MS APCI (+) m/z: 476.1, [M+H].

후처리

  1. washthe reaction mixture was washed with saturated NaHCO3 (aq.)
  2. washThe aqueous layer was washed with CH2Cl2 (10 mL×2)
  3. washThe combined organic layer was washed with water (10 mL) and brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography on silica gel (CH2Cl2/MeOH, 50:1

출처 및 근거

ORD 기록
ord-3885d88c95304059891122c18a805ec5
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09290468B2

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