Chlorotrimethylsilane → HCID 178470311, 화합물

HRID 1424455노트

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HRID 1424455 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[NH:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])(=[O:3])[NH2:2].C[Si](Cl)(C)C>ClCCCl>[Cl:10][C:7]1[CH:6]=[C:5]2[C:4]([C:1]([OH:3])=[N:2][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:11]2)=[CH:9][CH:8]=1

참가 물질

4

반응물 2

HCID 6397ChlorotrimethylsilaneHCID 66610703Ethyl 2-(2-carbamoyl-5-chlorophenylamino)-2-oxoacetate

생성물 1

HCID 178470311HCID 178470311, 화합물수율 63%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
80 °C

실험 절차

To a solution of ethyl 2-(2-carbamoyl-5-chlorophenylamino)-2-oxoacetate (545 mg, 2.02 mmol) and TEA (11 mL, 80 mmol) in DCE (20 mL) was added trimethylsilyl chloride (3.8 mL, 30 mmol) and the solution was stirred at 80° C. for 16 h. The mixture was concentrated under reduced pressure and the residue was partitioned between saturated aq NaHCO3 and DCM (100 mL). The separated aqueous phase was extracted with DCM (2×100 mL) and the combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 10-60% EtOAc/hexanes to afford ethyl 7-chloro-4-hydroxyquinazoline-2-carboxylate as a solid (321 mg, 63%). 1H NMR (300 MHz, DMSO-d6) δ 1.36 (t, J=7.06 Hz, 3H), 4.39 (q, J=7.10 Hz, 2H), 7.60-7.74 (m, 1H), 7.85-7.98 (m, 1H), 8.11-8.23 (m, 1H), 12.82 (br s, 1H).

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between saturated aq NaHCO3 and DCM (100 mL)
  3. extractionThe separated aqueous phase was extracted with DCM (2×100 mL)
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 10-60% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-2162cc7af87c44c291457a6edb337d0c
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927711B2

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