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Acetic Anhydride → HCID 11177772, 화합물

HRID 2216303
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HRID 2216303 반응식
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:4][N:3]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=2[CH3:17])[C:5]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([O:27][C:28](=[O:30])[CH3:29])=[CH:25][CH:26]=2)(=[O:20])=[O:19])=[CH:4][N:3]=1
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참가 물질

6

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HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 11361091HCID 11361091, 화합물

생성물 1

HCID 11177772HCID 11177772, 화합물수율 92%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 4-[2-methyl-4-(2,4,6-trimethyl-phenylamino)-pyrimidine-5-sulfonyl]-phenol (46 mg, 0.12 mmol), prepared as described in Example 2, acetic anhydride (0.023 mL, 0.24 mmol), triethylamine (0.05 mL, 0.36 mmol) and CH2Cl2 (4 mL) was stirred at room temperature under N2 for 4 h. The reaction mixture was treated with saturated sodium bicarbonate, and extracted (3×) with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (50:50 hexanes/EtOAc) to provide the target compound (47 mg, 92%) as a white solid: mp 142–144° C.; 1H NMR (300 MHz, CDCl3) δ 8.76 (s, 1H), 8.23 (br s, 1H), 7.99 (d, J=8.7 Hz, 2H), 7.29 (d, J=8.7 Hz, 2H), 6.92 (s, 2H), 2.40 (s, 3H), 2.33 (s, 3H), 2.31 (s, 3H), 2.01 (s, 6H); APCI MS m/z 426 [(M+H)+, calcd for C22H24N3O4S, 426.1].

후처리

  1. customprepared
  2. extractionextracted (3×) with CH2Cl2
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel (50:50 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-a30b5c4bc4754266b328fd3f239a6050
출처 데이터셋
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07112585B2

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