Water → 5-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile

HRID 412395노트

반응식

HRID 412395 반응식
[CH3:1][C:2]1([CH3:20])[C:7]2[CH:8]=[C:9]([C:12]3[NH:16][C:15]([C:17]#[N:18])=[CH:14][CH:13]=3)[CH:10]=[CH:11][C:6]=2[NH:5][C:4](=[O:19])[O:3]1.[C:21](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O>[CH3:1][C:2]1([CH3:20])[C:7]2[CH:8]=[C:9]([C:12]3[N:16]([CH3:21])[C:15]([C:17]#[N:18])=[CH:14][CH:13]=3)[CH:10]=[CH:11][C:6]=2[NH:5][C:4](=[O:19])[O:3]1

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 102209945-(4,4-Dimethyl-oxo-1,4-dihydro-2H-3,1-benzoxazine-6-yl)-1H-pyrrole-carbonitrile

생성물 1

HCID 99038535-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile수율 41%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrole-2-carbonitrile (1 eq, 71 mg, 0.27 mmol) in dimethylformamide (0.5 mL) was added potassium carbonate (5 eq, 0.18 g, 0.1.35 mmol). After 10 min., iodomethane (3 eq, 0.05 mL, 0.81 mmol) was added and the suspension was stirred for 2 h, poured into water (5 mL) and extracted with ethyl acetate (3×5 mL). The layers were separated, the aqueous layer was extracted with ethyl acetate (3×10 mL) and the combined organic layer was washed with brine, dried over MgSO4 and purified by flash column chromatography on silica gel eluting with 30% ethyl acetate/hexane to give 5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile (30 mg, 41%) as a white solid. 1H NMR (300 MHz, d6-DMSO) δ 1.64 (s, 6 H), 3.71 (s, 3 H), 6.33 (d, 1 H, J=4.1 Hz), 6.98 (d, 1H, J=8.0 Hz), 7.03 (d, 1H, J=4.1 Hz), 7.39 (m, 2 H), 10.39 (s, 1 H). MS (APCI (−)) m/z 280 (M−H)−. Anal. calcd for C16H15N3O2, C, 68.3, H, 5.37, N, 14.9. Found, C, 68.4, H, 5.51, N, 14.6.

후처리

  1. extractionextracted with ethyl acetate (3×5 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×10 mL)
  4. washthe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. custompurified by flash column chromatography on silica gel eluting with 30% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-1aea41e8d76a410081f1aaea24854430
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562857B2

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