Sodium hydride → HCID 178490658, 화합물

HRID 78540

반응식

HRID 78540 반응식
[C:1]([C:5]1[S:9][C:8]([NH:10][C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:25][C:26]1[CH:30]=[C:29]([CH3:31])[O:28][N:27]=1>CN(C=O)C.[Cl-].[Na+].O>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])/[N:7]([CH2:25][C:26]2[CH:30]=[C:29]([CH3:31])[O:28][N:27]=2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 27357633-(Chloromethyl)-5-methyl-1,2-oxazoleHCID 87094486n-(5-Tert-butylthiazol-2-yl)-5-chloro-2-methoxybenzamide

생성물 1

HCID 178490658HCID 178490658, 화합물수율 46.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

A solution of Example 244A (275 mg, 0.84 mmol) in DMF at 0° C. was treated with 60% NaH in mineral oil (40 mg, 1.03 mmol). After the gas evolution subsided, the reaction mixture was allowed to stir for 30 min and then treated with commercially available 3-(chloromethyl)-5-methylisoxazole (111 mg, 0.847 mmol). The resulting mixture was stirred at room temperature for 18 hr, poured into brine and extracted with EtOAc. The organics were combined and washed with water and brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography over silica gel using 20% EtOAc in hexane to afford the title compound (165 mg, 37% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.32 (s, 9H), 2.38 (s, 3H), 3.77 (s, 3H), 5.39 (s, 2H), 6.23 (s, 1H), 7.10 (d, J=8.8 Hz, 1H), 7.39 (s, 1H), 7.45 (dd, J=9.0, 2.9 Hz, 1H), 7.65 (d, J=3.1 Hz, 1H). MS (DCI) m/z 420 (M+H)+. Elemental analysis calculated for C20H22ClN3O3S: C, 57.20; H, 5.28; N, 10.01. Found: C, 57.16; H, 5.42; N, 9.75.

후처리

  1. stirringThe resulting mixture was stirred at room temperature for 18 hr
  2. extractionextracted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography over silica gel using 20% EtOAc in hexane

출처 및 근거

ORD 기록
ord-58dafc57c6de4064a16e2015623a5f11
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841334B2

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